Antimicrobial coating composition

Abstract

Described herein are quaternary ammonium polymer and interpenetrating polymer networks having broad spectrum antimicrobial properties, as well as compositions thereof, that produce fast acting, lasting, non-toxic, and non-allergic, colorless and transparent durable surface coatings that are water resistant and resistant to common solvents. The surface coatings are readily and cost-effectively produced from off-the-shelf materials using a variety of synthetic methods, enabling a wide range of chemical changes. The coating is readily applied to a wide range of surfaces and materials, and no material is leached from the coating.

Description

[0001] Cross - reference to related applications

[0002] This application claims the benefit of priority of U.S. Provisional Patent Application No. 63 / 410,722, filed on September 28, 2022, which is hereby incorporated by reference in its entirety. Technical Field

[0003] Embodiments of the present disclosure relate to broad-spectrum antimicrobial coating compositions and methods of using the same. More specifically, embodiments of the present disclosure relate to quaternary ammonium polymer structures and formulations having broad-spectrum antibacterial and antiviral properties. Background Art

[0004] Infectious diseases, including influenza, cause millions of deaths and hundreds of millions of illnesses globally each year. Since around 2020, the world has experienced the global COVID-19 pandemic caused by the highly transmissible novel coronavirus severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2).

[0005] The SARS-CoV-2 coronavirus and / or other viruses before it have been shown to spread from person to person via airborne droplets, but also via contact with virus-contaminated surfaces. A study conducted in 2020 in two major urban hospitals in the United States 1 concluded that healthcare-associated infections decreased by 36% when frequently touched surfaces (keyboards, countertops, railings, chairs, etc.) were coated with disinfectants. In fact, during the COVID-19 pandemic, disinfecting surfaces was adopted as a widespread health and safety practice, but with limited effectiveness as antiviral coatings become ineffective within a short time and require costly and labor-intensive frequent reapplication.

[0006] Over the years, many antimicrobial polymers have been developed in an attempt to provide more effective antibacterial / antiviral surface coatings. A recent review by Jarach et al. (2020) 2 highlighted some of the different polymer approaches to solving this problem. These polymers include nanoparticles with attached or adsorbed drugs, nanoparticles embedded with antiviral metals, naturally occurring polymers such as chitosan, silica particles with adsorbed quaternary ammonium salts, and quaternized polyethyleneimine (PEI).

[0007] Desirable antimicrobial surface coatings should have the following properties: (i) broad-spectrum antimicrobial activity at low minimum inhibitory concentration (MIC); (ii) rapid action; (iii) persistence; (iv) non-toxic and non-allergenic; (v) no material leaching from the coating; (vi) acceptable color, transparency, and appearance as a surface coating; (vii) easy to apply to a wide range of surfaces and materials; (viii) durability and resistance to water, alcohol, and common solvents; and (ix) easy and cost-effective to produce.

[0008] As understood by the inventors of the present application, conventional antimicrobial surface coatings lack many of the properties listed above. Therefore, there is a need for improved antimicrobial surface coating compositions. Summary of the Invention

[0009] Embodiments of the present technology provide water-based quaternary ammonium polymer coating formulations that can be applied to a wide range of surfaces to make the surfaces broadly antimicrobial. Different from conventional coatings, the water-based coatings disclosed herein (i) exhibit broad-spectrum antimicrobial activity at low minimum inhibitory concentration (MIC); (ii) have rapid action; (iii) are persistent; (iv) are non-toxic and non-allergenic; (v) have no material leaching from the coating; (vi) have acceptable color, transparency, and appearance as a surface coating; (vii) are easy to apply to a wide range of surfaces and materials; (viii) produce durable surface coatings that are resistant to water, alcohol, and common solvents; and (ix) are easy and cost-effective to produce.

[0010] In one aspect, the use of a reactive low molecular weight quaternary ammonium salt is described herein, the reactive low molecular weight quaternary ammonium salt comprising a long-chain hydrophobic group that gives the salt high surface activity and emulsifying efficacy in water. When the reactive quaternary ammonium salt reacts with a polyfunctional crosslinker (such as a polyisocyanate) and optionally an oligomeric polyol and / or a chain extender, the resulting reaction mixture becomes easy to emulsify in water and has excellent emulsion stability, especially in the presence of a water-soluble polymer as a protective colloid. The resulting emulsion can be coated or sprayed onto various surfaces or substrates while the chain extension or crosslinking reaction continues in the oil phase to form a highly durable antimicrobial coating after the film dries and is optionally post-cured. In some embodiments, the reactive low molecular weight quaternary ammonium salt comprises a long-chain hydrophobic group on the nitrogen of the quaternary ammonium salt.

[0011] In another aspect, the use of a reactive water-soluble protective colloid is described herein, the reactive water-soluble protective colloid forming an interpenetrating network with an antimicrobial polymer in the oil phase to further improve the durability of the resulting coating.

[0012] On the other hand, the present disclosure describes the use of a surface-active polyol in an oil phase for further improving emulsion stability, reducing the particle size of the resulting emulsion, and improving coating quality.

[0013] On the other hand, the present disclosure describes the use of a blocking agent for protecting the reaction product of a reactive surface-active quaternary ammonium salt and a polyfunctional crosslinking agent prior to an emulsification step to further improve emulsion stability and processability or the green time of the emulsion. Optionally, in the presence of a catalyst or sensitizer, the blocking agent is de-blocked during or after a drying and / or post-curing step, for example, by heating or radiation, to obtain a durable coating.

[0014] The antimicrobial efficiency of an organic solvent-based antimicrobial coating generally decreases as the crosslink density of the coating increases. Acceptable coating properties typically require a high degree of crosslinking, including durability and resistance to organic solvents, alcohol, water, detergents, and various disinfection solutions and processes. Unfortunately, when the crosslink density is high, the bioactive functional groups in the organic solvent-based coating tend to be trapped in the crosslink network. Different from such organic solvent-based antimicrobial coatings, the high surface activity of the reactive quaternary ammonium salts of the present technology allows bioactive functional groups including quaternary ammonium groups to diffuse to the interface of the emulsion droplets and then to the surface of the resulting coating. Therefore, by using the present technology, a durable coating with desired physical and chemical properties and high antimicrobial efficiency can be achieved simultaneously.

[0015] In one aspect, there is provided an antimicrobial composition comprising an oil-in-water emulsion comprising (i) an oil phase comprising a first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group to react with the first polyfunctional crosslinking agent; optionally a polyol; a polyethyleneimine intermediate or a second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinking agent; and optionally a third polyfunctional crosslinking agent; and (ii) an aqueous phase comprising a water-soluble polymer, wherein the polyethyleneimine intermediate comprises an optionally substituted hydroxyalkylene functional group that reacts with the first adduct and, if present, the second polyfunctional crosslinking agent; and at least a portion of the nitrogen atoms present in the polyethyleneimine intermediate are quaternized.

[0016] In one aspect, the water-soluble polymer is crosslinked with: (a) the first polyfunctional crosslinking agent as incorporated in the first adduct; (b) the second polyfunctional crosslinking agent as incorporated in the second adduct, when present; (c) the third polyfunctional crosslinking agent, when present; or (d) any combination of two or more of them.

[0017] In one aspect, the first quaternary ammonium salt has The chemical structure, where

[0018] R 1 is selected from the group consisting of: -(C8-C 30 alkyl), -(C8-C 30 heteroalkyl), -(C8-C 30 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl), -(C6-C 10 aryl)-(C8-C 30 alkyl), -(C6-C 10 aryl)-(C8-C 30 heteroalkyl), -(CR m R n ) x10 -W 10 -(CR p R q ) y10 -H and -(CR m R n ) x11 -W 11 -(CR p R q ) y11 H-; where -(C8-C 30 heteroalkyl), -(C8-C 30 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl)-(C8-C 30 heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S and Si;

[0019] R 2 is selected from the group consisting of: -(C1-C4 alkyl), -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl), -(C6-C 10 aryl)-(C1-C4 alkyl), -(C6-C 10 aryl)-(C1-C4 heteroalkyl), -(CR m R n ) x20 -W 20 -(CR p R q ) y20 -H and -(CR m R n ) x21 -W 21 -(CRp R q ) y21 -H; wherein -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl)-(C1-C4 heteroalkyl) have 1 to 2 heteroatoms independently selected from O, S, and Si;

[0020] R 3 is selected from the group consisting of: -(C1-C 30 alkyl), -(C1-C 30 heteroalkyl), -(C1-C 30 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl), -(C6-C 10 aryl)-(C1-C 30 alkyl), -(C6-C 10 aryl)-(C1-C 30 heteroalkyl); -(CR m R n ) x30 -W 30 -(CR p R q ) y30 -H and -(CR m R n ) x31 -W 31 -(CR p R q ) y31 -H; wherein -(C1-C 30 heteroalkyl), -(C1-C 30 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl)-(C1-C 30 heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S, and Si;

[0021] A is a linking group selected from the group consisting of: -(C3-C 20 alkylene)-, -(C3-C 20 heteroalkylene)-, -(C6-C 10 arylene)-(C3-C 20 alkylene)-, -(CR m R n ) x40 -W 40 -(CR p R q )y40 -and-(CR m R n ) x41 -W 41 -(CR p R q ) y41 -wherein-(C3-C 20 alkylene)-has 1 to 4 heteroatoms independently selected from O, S, and Si; and-(C3-C 20 alkylene)-and-(C3-C 20 heteroalkylene)-are optionally substituted with 1 to 6 substituents independently selected from:-(C6-C 10 aryl)-(C1-C3 alkyl),-(C6-C 10 aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 aryl),-(C1-C3 heteroalkyl)-(C6-C 10 aryl), and-(C6-C 10 aryl);

[0022] Each R m 、R n 、R p and R q is independently selected from H and C1-C4 alkyl;

[0023] W 10 、W 20 、W 30 and W 40 is independently selected from -C(O)-; -C(O)O-; -OC(O)-; -C(O)NH-; and -NHC(O)-;

[0024] W 11 、W 21 、W 31 and W 41 is independently selected from 5- to 6-membered cycloalkyl, C6-C 10 aryl, 5- to 6-membered heteroalkyl, and 5- to 6-membered heteroaryl, wherein the heteroalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si; and the heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si;

[0025] x10 is an integer from 1 to 30, and y10 is an integer from 0 to 29, where 8 ≤ (x10 + y10) ≤ 30;

[0026] x11 is an integer from 1 to 30, and y11 is an integer from 0 to 29, where 8 ≤ (x11 + y11) ≤ 30;

[0027] x20 is an integer from 1 to 4, and y20 is an integer from 0 to 3, where x20 + y20 ≤ 4;

[0028] x21 is an integer from 1 to 4, and y21 is an integer from 0 to 3, where x21 + y21 ≤ 4;

[0029] x30 is an integer from 1 to 30, and y30 is an integer from 0 to 29, where x30 + y30 ≤ 30;

[0030] x31 is an integer from 1 to 30, and y31 is an integer from 0 to 29, where x31 + y31 ≤ 30;

[0031] x40 is an integer from 1 to 19, and y40 is an integer from 1 to 19, where 3 ≤ (x40 + y40) ≤ 20;

[0032] x41 is an integer from 1 to 20, and y41 is an integer from 0 to 19, where 3 ≤ (x41 + y41) ≤ 20;

[0033] Y is selected from the group consisting of: -OH, -NHR 4 , -SH, -CO2H, -C(O)NHR 4 , -C(S)NHR 4 ,

[0034]

[0035] Each R 4 is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl), where -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S and Si; and

[0036] X - is independently an acetate ion, a halide ion, a sulfate ion, a sulfonate ion, a phosphate ion, a phosphonate ion, a carbonate ion, a silicate ion, a hexafluorophosphate ion, a hexafluoroantimonate ion, a trifluoromethanesulfonate ion, a borate ion or an organic substituted derivative of any of the foregoing.

[0037] On the one hand, R1 selected from the group consisting of: -(C 12 -C 30 -alkyl), -(C 12 -C 30 -heteroalkyl), -(C 12 -C 30 -alkyl)-(C6-C 10 -aryl), -(C 12 -C 30 -heteroalkyl)-(C6-C 10 -aryl), -(C6-C 10 -aryl)-(C 12 -C 30 -alkyl) and -(C6-C 10 -aryl)-(C 12 -C 30 -heteroalkyl); wherein -(C 12 -C 30 -heteroalkyl), -(C 12 -C 30 -heteroalkyl)-(C6-C 10 -aryl) and -(C6-C 10 -aryl)-(C 12 -C 30 -heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S, and Si.

[0038] In one aspect, R 3 is selected from the group consisting of: -(C1-C4 alkyl), -(C1-C4 heteroalkyl), -(C1-C4 alkyl)-(C6-C 10 -aryl), -(C1-C4 heteroalkyl)-(C6-C 10 -aryl), -(C6-C 10 -aryl)-(C1-C4 alkyl) and -(C6-C 10 -aryl)-(C1-C4 heteroalkyl); wherein -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 -aryl) and -(C6-C 10 -aryl)-(C1-C4 heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S, and Si.

[0039] In one aspect, R 2 and R 3 are methyl.

[0040] In one aspect, A is -(CH2) m - or -(CH2CHR 5 -O-) n CH2CHR 5-, where m is an integer from 2 to 20; n is 0, 1, 2, 3, 4 or 5; and each R 5 is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl), where -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S and Si.

[0041] On the one hand, each R 5 is independently H or methyl.

[0042] On the one hand, the first quaternary ammonium salt is

[0043] or a combination of two or more thereof.

[0044] On the one hand, based on the dry weight of the oil phase, the first quaternary ammonium salt is present in the oil phase in an amount of about 1 wt% to about 50 wt%.

[0045] On the one hand, based on the dry weight of the oil phase, the first quaternary ammonium salt is present in the oil phase in an amount of about 5 wt% to about 25 wt%.

[0046] On the one hand, based on the dry weight of the oil phase, the first multifunctional crosslinking agent incorporated into the first adduct is present in the oil phase in an amount of about 2 wt% to about 25 wt%.

[0047] On the one hand, based on the dry weight of the oil phase, the first multifunctional crosslinking agent incorporated into the first adduct is present in the oil phase in an amount of about 5 wt% to about 20 wt%.

[0048] On the one hand, based on the dry weight of the oil phase, the second multifunctional crosslinking agent incorporated into the second adduct is present in the oil phase in an amount of about 0.1 wt% to about 10 wt%.

[0049] On the one hand, based on the dry weight of the oil phase, the second multifunctional crosslinking agent incorporated into the second adduct is present in the oil phase in an amount of about 2 wt% to about 8 wt%

[0050] On the one hand, based on the dry weight of the oil phase, the third polyfunctional crosslinking agent is present in the oil phase in an amount of about 0.1 wt% to about 20 wt%.

[0051] On the one hand, based on the dry weight of the oil phase, the third polyfunctional crosslinking agent is present in the oil phase in an amount of about 2 wt% to about 15 wt%.

[0052] On the one hand, the first polyfunctional crosslinking agent is a first polyisocyanate; the second polyfunctional crosslinking agent, when present, is a second polyisocyanate; the third polyfunctional crosslinking agent, when present, is a third polyisocyanate; and the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate are different.

[0053] On the one hand, the first polyfunctional crosslinking agent is a first polyisocyanate; the second polyfunctional crosslinking agent, when present, is a second polyisocyanate; the third polyfunctional crosslinking agent, when present, is a third polyisocyanate; and the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate are the same.

[0054] On the one hand, the average isocyanate functionality of each of the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate is from 2 to 5.

[0055] On the one hand, the average isocyanate functionality of each of the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate is from 3 to 4.

[0056] On the one hand, each of the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate is prepared from a diisocyanate independently selected from the group consisting of: hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), m-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

[0057] On the one hand, each of the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate is independently selected from the group consisting of: N-3300, N-100, Z4470SN, T series polyisocyanates and M series polyisocyanates.

[0058] On the one hand, the average isocyanate functionality of the first adduct is from 2 to 3.

[0059] On the one hand, the average isocyanate functionality of the first adduct is from about 2.05 to about 2.3.

[0060] On the one hand, the reactive isocyanate functional groups on the first adduct are protected with a blocking agent.

[0061] On the one hand, the blocking agent is selected from the group consisting of: oximes, phenols, malonic esters, alcohols, lactams, dicarbonyl compounds, isohydroxamic acid esters, bisulfite addition compounds, hydroxylamines, esters of p-hydroxybenzoic acid and salicylic acid.

[0062] On the one hand, the blocking agent is selected from the group consisting of: acetone oxime, methyl ethyl ketone oxime, sodium bisulfite, diethyl malonate and 3,5-dimethylpyrazole.

[0063] On the one hand, the antimicrobial composition further comprises a deblocking agent.

[0064] On the one hand, the deblocking agent is selected from the group consisting of: organotin, organobismuth and tertiary amines.

[0065] On the one hand, based on the dry weight of the oil phase, the first adduct is present in the oil phase in an amount of from about 5 wt% to about 70 wt%.

[0066] On the one hand, based on the dry weight of the oil phase, the second adduct is present in the oil phase in an amount of from about 1 wt% to about 30 wt%.

[0067] On the one hand, based on the dry weight of the oil phase, the second adduct is present in the oil phase in an amount of from about 3 wt% to about 15 wt%.

[0068] On the one hand, the oil phase further comprises an organic solvent or a diluent.

[0069] On the one hand, the organic solvent or diluent in the oil phase is water-miscible.

[0070] On the one hand, the organic solvent or diluent is acetone.

[0071] On the one hand, based on the weight of the oil phase, the organic solvent or diluent is present in the oil phase in an amount of from about 5 wt% to about 35 wt%.

[0072] On the one hand, based on the weight of the oil phase, the organic solvent or diluent is present in the oil phase in an amount of from about 10 wt% to about 30 wt%.

[0073] On the one hand, when present, the polyol is selected from the group consisting of: polyether polyols, polyester polyols, polyacrylic polyols, polymethacrylic polyols, polycaprolactone polyols, polybutadiene polyols, poly(acrylonitrile-co-butadiene) polyols, polysiloxane polyols, copolymers of any two or more thereof, and combinations of any two or more thereof.

[0074] On the one hand, the polyol is selected from the group consisting of: poly(tetramethylene glycol), polyethylene glycol, polypropylene glycol, poly(ethylene glycol-b-propylene glycol-b-ethylene glycol), and poly(propylene glycol-b-polyethylene glycol-b-propylene glycol).

[0075] On the one hand, the polyol has a weight average molecular weight of from about 300 to about 3000.

[0076] On the one hand, the polyol has a weight average molecular weight of from about 400 to about 2000.

[0077] On the one hand, the polyol has a weight average molecular weight of from about 600 to about 1500.

[0078] On the one hand, based on the dry weight of the oil phase, the polyol is present in the oil phase in an amount of from about 1 wt% to about 40 wt%.

[0079] On the one hand, based on the dry weight of the oil phase, the polyol is present in the oil phase in an amount of from about 5 wt% to about 25 wt%.

[0080] On the one hand, the water-soluble polymer is selected from the group consisting of: hydroxyethyl cellulose (HEC), hydroxypropyl cellulose, polyvinyl alcohol, poly(hydroxyethyl methacrylate-co-alkyl methacrylate), poly(hydroxyethyl methacrylate-co-alkyl acrylate), poly(acrylate hydroxyethyl ester-co-alkyl methacrylate), poly(acrylate hydroxyethyl ester-co-alkyl acrylate), polyacrylamide, polyethyleneimine intermediate, copolymers of two or more thereof, copolymers of one or more thereof with polyvinylpyrrolidone poly(glycidyl acrylate) or with poly(glycidyl methacrylate), and combinations or blends of two or more thereof.

[0081] On the one hand, the water-soluble polymer is hydroxyethyl cellulose or a hydrophobically modified derivative thereof.

[0082] On the one hand, the water-soluble polymer is a polyethyleneimine intermediate.

[0083] On the one hand, the water-soluble polymer is present in the aqueous phase in an amount of from about 0.5 wt% to about 15 wt% of the dry weight of the oil phase.

[0084] On the one hand, the water-soluble polymer is present in the aqueous phase in an amount of about 3 wt% to about 12 wt% based on the dry weight of the oil phase.

[0085] On the one hand, the water-soluble polymer is present in the aqueous phase in an amount of about 5 wt% to about 10 wt% based on the dry weight of the oil phase.

[0086] On the one hand, the aqueous phase further comprises a surfactant.

[0087] On the one hand, the surfactant is a nonionic surfactant.

[0088] On the one hand, the nonionic surfactant has an average HLB (hydrophilic-lipophilic balance) value of about 12 to about 15.

[0089] On the one hand, the nonionic surfactant is selected from TRITON TM X-114 ((1,1,3,3-tetramethylbutyl)phenyl-polyethylene glycol), SILWET TM L-7604 (siloxane polyalkylene oxide copolymer) and combinations thereof.

[0090] On the one hand, based on the dry weight of the oil phase, the surfactant is present in the aqueous phase in an amount of about 0.05 wt% to about 2 wt%.

[0091] On the one hand, based on the dry weight of the oil phase, the surfactant is present in the aqueous phase in an amount of about 0.1 wt% to about 1 wt%.

[0092] On the one hand, the aqueous phase further comprises an antifoaming agent or defoaming agent.

[0093] On the one hand, the antifoaming agent is ST 2410 (star-polymer based antifoaming agent).

[0094] On the one hand, the random polymer or interpenetrating polymer network is produced by random polymerization / crosslinking of: the first adduct; the polyethyleneimine intermediate or the second adduct; when present, the polyol; if reactive, the water-soluble polymer; and when present, the third polyfunctional crosslinking agent.

[0095] On the one hand, the oil phase further comprises a third adduct of the first polyfunctional crosslinking agent and a second quaternary ammonium salt where

[0096] R 1a 、R 2a and R 3a are each independently methyl or ethyl;

[0097] A 1A linking group selected from the group consisting of: -(C3-C 20 alkylene)-, -(C3-C 20 heteroalkylene)-, -(C6-C 10 arylene)-(C3-C 20 alkylene)-, -(CR m1 R n1 ) x42 -W 42 -(CR p1 R q1 ) y42 - and -(CR m1 R n1 ) x43 -W 43 -(CR p1 R q1 ) y43 -, where -(C3-C 20 heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; and -(C3-C 20 alkylene)- and -(C3-C 20 heteroalkylene)- are optionally substituted with 1 to 6 substituents independently selected from the following: -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl);

[0098] Each R m1 , R n1 , R p1 and R q1 is independently selected from H and C1-C4 alkyl;

[0099] W 42 is selected from -C(O)-; -C(O)O-; -OC(O)-; -C(O)NH-; and -NHC(O)-;

[0100] W 43 is selected from 5- to 6-membered cycloalkyl, C6-C 10 aryl, 5- to 6-membered heteroalkyl, and 5- to 6-membered heteroaryl, where the heteroalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si; and the heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si;

[0101] x42 is an integer from 1 to 19, and y42 is an integer from 1 to 19, where 3 ≤ (x42 + y42) ≤ 20;

[0102] x43 is an integer from 1 to 20, and y43 is an integer from 0 to 19, where 3 ≤ (x43 + y43) ≤ 20;

[0103] Y 1 is selected from the group consisting of: -OH, -NHR 4a , -SH, -CO2H, -C(O)NHR 4a , -C(S)NHR 4a ,

[0104]

[0105] Each R 4a is independently selected from the group consisting of: H, -(C6 - C 10 aryl)-(C1 - C3 alkyl), -(C6 - C 10 aryl)-(C1 - C3 heteroalkyl), -(C1 - C3 alkyl)-(C6 - C 10 aryl), -(C1 - C3 heteroalkyl)-(C6 - C 10 aryl) and -(C6 - C 10 aryl), where -(C6 - C 10 aryl)-(C1 - C3 heteroalkyl) and -(C1 - C3 heteroalkyl)-(C6 - C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si; and

[0106] X - is independently an acetate ion, a halide ion, a sulfate ion, a sulfonate ion, a phosphate ion, a phosphonate ion, a carbonate ion, a silicate ion, a hexafluorophosphate ion, a hexafluoroantimonate ion, a trifluoromethanesulfonate ion, a borate ion, or an organically substituted derivative of any of the foregoing.

[0107] On the one hand, the oil phase further comprises a third adduct of the fourth polyfunctional crosslinking agent and a secondary quaternary ammonium salt where

[0108] R 1a , R 2a and R 3a are each independently methyl or ethyl;

[0109] A 1 is a linking group selected from the group consisting of: -(C3 - C 20 alkylene)-, -(C3 - C 20 heteroalkylene)-, -(C6 - C10 arylene)-(C3-C 20 alkylene)-, -(CR m1 R n1 ) x42 -W 42 -(CR p1 R q1 ) y42 - and -(CR m1 R n1 ) x43 -W 43 -(CR p1 R q1 ) y43 -, wherein -(C3-C 20 heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; and -(C3-C 20 alkylene)- and -(C3-C 20 heteroalkylene)- are optionally substituted with 1 to 6 substituents independently selected from: -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl);

[0110] Each R m1 , R n1 , R p1 , and R q1 is independently selected from H and C1-C4 alkyl;

[0111] W 42 is selected from -C(O)-; -C(O)O-; -OC(O)-; -C(O)NH-; and -NHC(O)-;

[0112] W 43 is selected from 5- to 6-membered cycloalkyl, C6-C 10 aryl, 5- to 6-membered heteroalkyl, and 5- to 6-membered heteroaryl, wherein the heteroalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si; and the heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si;

[0113] x42 is an integer from 1 to 19, and y42 is an integer from 1 to 19, where 3 ≤ (x42 + y42) ≤ 20;

[0114] x43 is an integer from 1 to 20, and y43 is an integer from 0 to 19, where 3 ≤ (x43 + y43) ≤ 20;

[0115] Y 1 is selected from the group consisting of: -OH, -NHR 4a 、-SH, -CO2H, -C(O)NHR 4a 、-C(S)NHR 4a 、

[0116]

[0117] Each R 4a is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl), where -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si; and

[0118] X - is independently an acetate ion, a halide ion, a sulfate ion, a sulfonate ion, a phosphate ion, a phosphonate ion, a carbonate ion, a silicate ion, a hexafluorophosphate ion, a hexafluoroantimonate ion, a trifluoromethanesulfonate ion, a borate ion, or an organic substituted derivative of any of the foregoing.

[0119] In one aspect, the fourth polyfunctional crosslinker is different from the first polyfunctional crosslinker and, when present, different from the second polyfunctional crosslinker and, when present, different from the third polyfunctional crosslinker.

[0120] In one aspect, based on the dry weight of the oil phase, the fourth polyisocyanate is present in the oil phase in an amount of about 0.1 wt% to about 15 wt%.

[0121] In one aspect, the fourth polyfunctional crosslinker is a fourth polyisocyanate.

[0122] In one aspect, the average isocyanate functionality of the fourth polyisocyanate is 2 to 5.

[0123] On the one hand, the fourth polyisocyanate is prepared from a diisocyanate selected from the group consisting of: hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), m-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

[0124] On the one hand, the fourth polyisocyanate is selected from the group consisting of: N-3300, N-100, Z4470SN, T-series polyisocyanates and M-series polyisocyanates.

[0125] On the one hand, the second quaternary ammonium salt is (C2DMDEG-Br).

[0126] On the one hand, based on the dry weight of the oil phase, the second quaternary ammonium salt is present in the oil phase in an amount of about 1 wt% to about 15 wt%.

[0127] On the one hand, based on the dry weight of the oil phase, the second quaternary ammonium salt is present in the oil phase in an amount of about 3 wt% to about 10 wt%.

[0128] On the one hand, the average isocyanate functionality of the third adduct is 2 to 3.

[0129] On the one hand, the average isocyanate functionality of the third adduct is about 2.05 to about 2.3.

[0130] On the one hand, based on the dry weight of the oil phase, the third adduct is present in the oil phase in an amount of about 2 wt% to about 30 wt%.

[0131] On the one hand, the reactive isocyanate functional groups on the third adduct are protected with a blocking agent.

[0132] On the one hand, the blocking agent for the reactive isocyanate functional groups on the third adduct is selected from the group consisting of: oximes, phenols, malonic esters, alcohols, lactams, dicarbonyl compounds, isohydroxamic acid esters, bisulfite addition compounds, hydroxylamines, esters of p-hydroxybenzoic acid and salicylic acid.

[0133] On the one hand, the blocking agent for the reactive isocyanate functional groups on the third adduct is selected from the group consisting of: acetone oxime, methyl ethyl ketoxime, sodium bisulfite, diethyl malonate, and 3,5-dimethylpyrazole.

[0134] On the one hand, the random polymer or interpenetrating polymer network is produced by random polymerization / crosslinking of: the first adduct; the polyethyleneimine intermediate or the second adduct; the third adduct; when present, the polyol; if reactive, the water-soluble polymer; and when present, the third polyfunctional crosslinking agent.

[0135] On the one hand, the oil phase further comprises a chain extender selected from the group consisting of: HO-(C n H 2n )-OH and HO-(C n H 2n-2 )-OH or a combination thereof, where n is an integer from 2 to 8.

[0136] On the one hand, the chain extender is propylene glycol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexanedimethanol or a combination of two or more thereof.

[0137] On the one hand, based on the dry weight of the oil phase, the chain extender is present in the oil phase in an amount of up to about 10% by weight.

[0138] On the one hand, based on the dry weight of the oil phase, the chain extender is present in the oil phase in an amount of about 0.5% by weight to about 10% by weight.

[0139] On the one hand, the random polymer or interpenetrating polymer network is produced by random polymerization / crosslinking of: the first adduct; the polyethyleneimine intermediate or the second adduct; when present, the third adduct; when present, the polyol; the chain extender; if reactive, the water-soluble polymer; and when present, the third polyfunctional crosslinking agent.

[0140] On the one hand, based on the dry weight of the oil phase, the polyethyleneimine intermediate is present in the oil phase in an amount of about 0.1% by weight to about 50% by weight.

[0141] On the one hand, the hydroxyalkylene functional group is optionally substituted with a C1-C6 alkyl group, and the C1-C6 alkyl group is optionally substituted with a substituent selected from: -N + (R 20 )3X - 、-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl) and carboxyl; each R 20 is independently selected from the group consisting of: C1-C 18Alkyl; C1-C with heteroatoms independently selected from O, S, Si, and tert-substituted N, with 1 to 4 such heteroatoms 18 Heteroalkyl; and C6-C optionally substituted with the following 10 Aryl: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl); and each X - Is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion, and borate ion, and their organically substituted derivatives.

[0142] On the one hand, the hydroxyalkylene functional group is hydroxyethylene, hydroxypropylene, hydroxybutylene, or an oligomer thereof.

[0143] On the one hand, the polyethyleneimine intermediate comprises the reaction product of reagents, the reagents comprising polyethyleneimine, a monoepoxide, and an alkylating agent, wherein the monoepoxide is optionally substituted with a C1-C6 alkyl group, and the C1-C6 alkyl group is optionally substituted with substituents selected from the following: -(C6-C 10 Aryl) and -(C1-C6 alkoxy) optionally substituted with a hydroxyl group, C1-C6 alkoxy, C6-C optionally substituted with a C1-C6 alkyl group 10 Aryl and carboxyl.

[0144] On the one hand, the monoepoxide is a C1-C6 alkyl epoxide.

[0145] On the one hand, the C1-C6 alkyl epoxide is selected from the group consisting of propyl epoxide, butyl epoxide, and hexyl epoxide.

[0146] On the one hand, the polyethyleneimine intermediate comprises the reaction product of reagents, the reagents comprising polyethyleneimine, a monoepoxide, and optionally an alkylating agent; the monoepoxide is substituted with -(C1-C6 alkyl)-N + (R 20 )3X - Substituted; each R 20 Is independently selected from the group consisting of C1-C 18 Alkyl; C1-C with heteroatoms independently selected from O, S, Si, and tert-substituted N, with 1 to 4 such heteroatoms 18 Heteroalkyl; and C6-C optionally substituted with the following 10Aryl: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2 or -OC(O)-(C1-C6 alkyl); and each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and their organically substituted derivatives.

[0147] On the one hand, the alkylating agent comprises one or more R 21 -LG, wherein each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH; and each LG is a leaving group.

[0148] On the one hand, the alkylating agent is benzyl halide or hexyl halide.

[0149] On the one hand, the polyethyleneimine intermediate comprises the reaction product of reagents comprising polyethyleneimine and haloalkanol.

[0150] On the one hand, the haloalkanol is X 30 -(C2-C6 alkylene)-OH, wherein X 30 is Cl, Br or I.

[0151] On the one hand, the reagents of the reaction product comprised in the polyethyleneimine intermediate further comprise monoisocyanate.

[0152] On the one hand, the monoisocyanate comprises one or more R 30 -NCO, wherein each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1-3 substituents independently selected from: halogen, -SiR a (OR b )(OR c ) and -(C6-C 10 aryl); and (2) C6-C 10 aryl optionally substituted with 1-3 substituents independently selected from: halogen, -(C1-C6 alkyl) and -SiR a(OR b )(OR c ); wherein each R a is independently a C1-C6 alkyl group; and each R b and each R c is independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3.

[0153] On the one hand, the mono-isocyanate comprises octyl isocyanate, octadecyl isocyanate or a combination thereof.

[0154] On the one hand, the molecular weight of the polyethyleneimine is from about 300 Daltons to about 270,000 Daltons.

[0155] On the one hand, the molecular weight of the polyethyleneimine is from about 10,000 Daltons to about 200,000 Daltons.

[0156] On the one hand, the molecular weight of the polyethyleneimine is from about 25,000 Daltons to about 120,000 Daltons.

[0157] On the one hand, the polyethyleneimine is branched.

[0158] On the one hand, the polyethyleneimine is hyperbranched.

[0159] On the one hand, the ratio of primary amine: secondary amine: tertiary amine of the polyethyleneimine is from about 1:2:1 to about 1:1:1.

[0160] On the one hand, the ratio of primary amine: secondary amine: tertiary amine of the polyethyleneimine is about 1:1:0.7.

[0161] On the one hand, the polyethyleneimine intermediate is selected from

[0162]

[0163] or a copolymer of two or more of them, wherein:

[0164] Each Y 3 is independently H or -O-Y 2 , wherein each Y 3 cannot be H;

[0165] Each Y 2 is independently H or -C(O)-NHR 30 , wherein each Y 2 cannot be -C(O)-NHR 30 ;

[0166] Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000;

[0167] Z is -(C2-C6 alkylene)-;

[0168] Each R 10 is independently selected from hydrogen; C1-C6 alkyl optionally substituted with a substituent selected from the following: -N + (R 20 )3X - 、-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl; and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted with the following: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl);

[0169] Each R 21 is independently selected from C1-C6 alkyl optionally substituted with a substituent selected from the following: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with -OH;

[0170] Each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1 to 3 substituents independently selected from the following: halogen, –SiR a (OR b )(OR c ) and -(C6-C 10 aryl); and (2) C6-C 10 aryl optionally substituted with 1 to 3 substituents independently selected from the following: halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c ); wherein each R ais independently a C1-C6 alkyl group; and each R b and each R c is independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3; and

[0171] each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and their organically substituted derivatives;

[0172] provided that:

[0173] when R 10 is a C1-C6 alkyl group optionally substituted with a substituent selected from the following, then the polyethyleneimine intermediate is selected from -(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl) and carboxyl group.

[0174] On the one hand, the polyethyleneimine intermediate is

[0175] where each n is an integer independently selected from 1 to

[0176] 3000, preferably an integer independently selected from 10 to 1000.

[0177] On the one hand, at least 20% of the nitrogen atoms in the polyethyleneimine intermediate are quaternized.

[0178] On the one hand, the second adduct has the formula (I):

[0179]

[0180] wherein:

[0181] each A is independently selected from

[0182] or a copolymer of any two or more of them; and the attachment of each A forms a carbamate bond;

[0183] each Y 3 is independently H or -O-Y 2 , where each Y3 It cannot be H;

[0184] Each Y 2 is independently H or -C(O)-NHR 30 wherein each Y 2 cannot be -C(O)-NHR 30 ;

[0185] Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000;

[0186] Z is -(C2-C6 alkylene)-;

[0187] Each R 10 is independently selected from hydrogen; C1-C6 alkyl optionally substituted with substituents selected from the following: -N + (R 20 )3X - 、-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl; and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tert-substituted N; and C6-C 10 aryl optionally substituted with the following: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl);

[0188] Each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from the following: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with -OH;

[0189] Each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1-3 substituents independently selected from the following: halogen, –SiR a (OR b )(OR cand -(C6-C 10 aryl); (2) C6-C optionally substituted with 1-3 substituents independently selected from the following 10 aryl: halogen, -(C1-C6 alkyl), and –SiR a (OR b )(OR c ); and (3) wherein each R a is independently -(C1-C6 alkyl); and each R b and each R c is independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3;

[0190] each R 40 is independently -(C1-C 10 alkylene)- optionally substituted with phenyl or a 3- to 8-membered cycloalkyl ring; and

[0191] each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion, and borate ion, and their organically substituted derivatives;

[0192] provided that:

[0193] when R 10 is C1-C6 alkyl optionally substituted with a substituent selected from the following, then each A is independently selected from -(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl.

[0194] On the one hand, the second adduct has the formula (II):

[0195]

[0196] wherein:

[0197] each A is independently selected from or a copolymer of any two or more thereof; and the attachment of each A forms a urethane bond;

[0199] each Y 3 is independently H or -O-Y 2 , wherein each Y3 It cannot be H;

[0200] Each Y 2 is independently H or –C(O)-NHR 30 , wherein each Y 2 cannot be -C(O)-NHR 30 ;

[0201] Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000;

[0202] Z is -(C2-C6 alkylene)-;

[0203] Each R 10 is independently selected from hydrogen; C1-C6 alkyl optionally substituted with substituents selected from the following: -N + (R 20 )3X - 、-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl; and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted with the following: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl);

[0204] Each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from the following: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with -OH;

[0205] Each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1 to 3 substituents independently selected from the following: halogen, –SiR a (OR b )(OR cand -(C6-C 10 aryl); (2) C6-C 10 aryl optionally substituted with 1-3 substituents independently selected from the following: halogen, -(C1-C6 alkyl), and –SiR a (OR b )(OR c ); and (3) wherein each R a is independently -(C1-C6 alkyl); and each R b and each R c is independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3;

[0206] each R 40 is independently -(C1-C 10 alkylene)- optionally substituted with phenyl or a 3- to 8-membered cycloalkyl ring; and

[0207] each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion, and borate ion, and organically substituted derivatives thereof;

[0208] provided that:

[0209] when R 10 is C1-C6 alkyl optionally substituted with a substituent selected from the following, then each A is independently selected from -(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl.

[0210] There is provided a polymer or an interpenetrating polymer network comprising a random polymerization / crosslinking product of reagents, said reagents comprising (i) a first polyfunctional crosslinker and a first adduct of a first quaternary ammonium salt; (ii) a polyol; (iii) a polyethyleneimine intermediate or a second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinker; and (iv) optionally a third polyfunctional crosslinker.

[0211] On the one hand, in the polymer or interpenetrating polymer network, the first quaternary ammonium salt has a chemical structure of, wherein

[0212] R 1 is selected from the group consisting of -(C8-C30 alkyl), -(C8-C 30 heteroalkyl), -(C8-C 30 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl), -(C6-C 10 aryl)-(C8-C 30 alkyl), -(C6-C 10 aryl)-(C8-C 30 heteroalkyl), -(CR m R n ) x10 -W 10 -(CR p R q ) y10 -H and -(CR m R n ) x11 -W 11 -(CR p R q ) y11 H-; wherein -(C8-C 30 heteroalkyl), -(C8-C 30 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl)-(C8-C 30 heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S, and Si;

[0213] R 2 is selected from the group consisting of: -(C1-C4 alkyl), -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl), -(C6-C 10 aryl)-(C1-C4 alkyl), -(C6-C 10 aryl)-(C1-C4 heteroalkyl); -(CR m R n ) x20 -W 20 -(CR p R q ) y20 -H and -(CR m R n ) x21 -W 21 -(CR p R q ) y21 -H; wherein -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C10 aryl) and -(C6-C 10 aryl)-(C1-C4 heteroalkyl) having 1 to 4 heteroatoms independently selected from O, S, and Si;

[0214] R 3 selected from the group consisting of: -(C1-C 30 alkyl), -(C1-C 30 heteroalkyl), -(C1-C 30 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl), -(C6-C 10 aryl)-(C1-C 30 alkyl), -(C6-C 10 aryl)-(C1-C 30 heteroalkyl), -(CR m R n ) x30 -W 30 -(CR p R q ) y30 -H and -(CR m R n ) x31 -W 31 -(CR p R q ) y31 -H; wherein -(C1-C 30 heteroalkyl), -(C1-C 30 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl)-(C1-C 30 heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S, and Si;

[0215] A is a linking group selected from the group consisting of: -(C3-C 20 alkylene)-, -(C3-C 20 heteroalkylene)-, -(C6-C 10 arylene)-(C3-C 20 alkylene)-, -(CR m R n ) x40 -W 40 -(CR p R q ) y40 - and -(CR m R n ) x41 -W 41 -(CRp R q ) y41 -, wherein -(C3-C 20 heteroalkyl)- has 1 to 4 heteroatoms independently selected from O, S and Si; and -(C3-C 20 alkylene)- and -(C3-C 20 heteroalkyl)- are optionally substituted by 1 to 6 substituents independently selected from the following: -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl);

[0216] Each R m 、R n 、R p and R q is independently selected from H and C1-C4 alkyl;

[0217] W 10 、W 20 、W 30 and W 40 are independently selected from -C(O)-; -C(O)O-; -OC(O)-; -C(O)NH-; and -NHC(O)-;

[0218] W 11 、W 21 、W 31 and W 41 are independently selected from 5- to 6-membered cycloalkyl, C6-C 10 aryl, 5- to 6-membered heteroalkyl and 5- to 6-membered heteroaryl, wherein the heteroalkyl contains 1-2 ring heteroatoms selected from O, N, S and Si; and the heteroaryl contains 1-3 ring heteroatoms selected from O, N, S and Si;

[0219] x10 is an integer from 1 to 30, and y10 is an integer from 0 to 29, where 8 ≤ (x10 + y10) ≤ 30;

[0220] x11 is an integer from 1 to 30, and y11 is an integer from 0 to 29, where 8 ≤ (x11 + y11) ≤ 30;

[0221] x20 is an integer from 1 to 4, and y20 is an integer from 0 to 3, where x20 + y20 ≤ 4;

[0222] x21 is an integer from 1 to 4, and y21 is an integer from 0 to 3, where x21 + y21 ≤ 4;

[0223] x30 is an integer from 1 to 30, and y30 is an integer from 0 to 29, where x30 + y30 ≤ 30;

[0224] x31 is an integer from 1 to 30, and y31 is an integer from 0 to 29, where x31 + y31 ≤ 30;

[0225] x40 is an integer from 1 to 19, and y40 is an integer from 1 to 19, where 3 ≤ (x40 + y40) ≤ 20;

[0226] x41 is an integer from 1 to 20, and y41 is an integer from 0 to 19, where 3 ≤ (x41 + y41) ≤ 20;

[0227] Y is selected from the group consisting of: -OH, -NHR 4 、-SH, -CO2H, -C(O)NHR 4 、-C(S)NHR 4 、

[0228]

[0229] Each R 4 is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl), where -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S and Si; and

[0230] X - is independently an acetate ion, a halide ion, a sulfate ion, a sulfonate ion, a phosphate ion, a phosphonate ion, a carbonate ion, a silicate ion, a hexafluorophosphate ion, a hexafluoroantimonate ion, a trifluoromethanesulfonate ion, a borate ion or an organic substituted derivative of any of the foregoing.

[0231] In one aspect of the polymer or interpenetrating polymer network, R 1 is selected from the group consisting of: -(C 12 -C 30-(C1-C4 alkyl), -(C 12 -C 30 -(C1-C4 heteroalkyl), -(C 12 -C 30 -(C1-C4 alkyl)-(C6-C 10 -aryl), -(C 12 -C 30 -(C1-C4 heteroalkyl)-(C6-C 10 -aryl), -(C6-C 10 -aryl)-(C 12 -C 30 -alkyl) and -(C6-C 10 -aryl)-(C 12 -C 30 -heteroalkyl); wherein -(C 12 -C 30 -heteroalkyl), -(C 12 -C 30 -heteroalkyl)-(C6-C 10 -aryl) and -(C6-C 10 -aryl)-(C 12 -C 30 -heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si.

[0232] In one aspect of the polymer or interpenetrating polymer network, R 3 is selected from the group consisting of: -(C1-C4 alkyl), -(C1-C4 heteroalkyl), -(C1-C4 alkyl)-(C6-C 10 -aryl), -(C1-C4 heteroalkyl)-(C6-C 10 -aryl), -(C6-C 10 -aryl)-(C1-C4 alkyl) and -(C6-C 10 -aryl)-(C1-C4 heteroalkyl); wherein -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 -aryl) and -(C6-C 10 -aryl)-(C1-C4 heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si.

[0233] In one aspect of the polymer or interpenetrating polymer network, R 2 and R 3 are methyl.

[0234] In one aspect of the polymer or interpenetrating polymer network, A is -(CH2) m - or -(CH2CHR 5 -O-) n CH2CHR 5-, where m is an integer from 2 to 20; n is 0, 1, 2, 3, 4 or 5; and each R 5 is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl), where -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S and Si.

[0235] In one aspect of the polymer or interpenetrating polymer network, R 5 is H or methyl.

[0236] In one aspect of the polymer or interpenetrating polymer network, the first quaternary ammonium salt is

[0237] or a combination of two or more thereof.

[0238] In one aspect of the polymer or interpenetrating polymer network, the first quaternary ammonium salt is present in the dry polymer or interpenetrating polymer network in an amount of about 1 wt.% to about 50 wt.%.

[0239] In one aspect of the polymer or interpenetrating polymer network, the first polyfunctional crosslinker is a first polyisocyanate; the second polyfunctional crosslinker, when present, is a second polyisocyanate; the third polyfunctional crosslinker, when present, is a third polyisocyanate; and the first polyisocyanate, the second polyisocyanate and the third polyisocyanate are different.

[0240] In one aspect of the polymer or interpenetrating polymer network, the first polyfunctional crosslinker is a first polyisocyanate; the second polyfunctional crosslinker, when present, is a second polyisocyanate; the third polyfunctional crosslinker, when present, is a third polyisocyanate; and the first polyisocyanate, the second polyisocyanate and the third polyisocyanate are the same.

[0241] In one aspect of the polymer or interpenetrating polymer network, the average isocyanate functionality of each of the first polyisocyanate, the second polyisocyanate and the third polyisocyanate is 2 to 5.

[0242] In one aspect of the polymer or interpenetrating polymer network, the average isocyanate functionality of each of the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate is from 3 to 4.

[0243] In one aspect of the polymer or interpenetrating polymer network, each of the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate is prepared from a diisocyanate independently selected from the group consisting of: hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), trimethylhexamethylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

[0244] In one aspect of the polymer or interpenetrating polymer network, each of the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate is independently selected from the group consisting of: N-3300, N-100, Z4470SN, T series polyisocyanates and M series polyisocyanates.

[0245] In one aspect of the polymer or interpenetrating polymer network, the first polyfunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of from about 2 wt.% to about 25 wt.%.

[0246] In one aspect of the polymer or interpenetrating polymer network, the second polyfunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1 wt.% to about 10 wt.%.

[0247] In one aspect of the polymer or interpenetrating polymer network, the third polyfunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1 wt.% to about 20 wt.%.

[0248] In one aspect of the polymer or interpenetrating polymer network, the average isocyanate functionality of the first adduct is from 2 to 3.

[0249] In one aspect of the polymer or interpenetrating polymer network, the average isocyanate functionality of the first adduct is from about 2.05 to about 2.3.

[0250] In one aspect of the polymer or interpenetrating polymer network, the polyol is selected from the group consisting of: polyether polyols, polyester polyols, polyacrylic polyols, polymethacrylic polyols, polycaprolactone polyols, polybutadiene polyols, poly(acrylonitrile-co-butadiene) polyols, polysiloxane polyols, copolymers of any two or more thereof, and combinations of any two or more thereof.

[0251] In one aspect of the polymer or interpenetrating polymer network, the polyol is selected from the group consisting of: poly(tetramethylene glycol), polyethylene glycol, polypropylene glycol, poly(ethylene glycol-b-propylene glycol-b-ethylene glycol), and poly(propylene glycol-b-polyethylene glycol-b-propylene glycol).

[0252] In one aspect of the polymer or interpenetrating polymer network, the polyol has a weight average molecular weight of from about 300 to about 3000.

[0253] In one aspect of the polymer or interpenetrating polymer network, the polyol has a weight average molecular weight of from about 400 to about 2000.

[0254] In one aspect of the polymer or interpenetrating polymer network, the polyol has a weight average molecular weight of from about 600 to about 1500.

[0255] In one aspect of the polymer or interpenetrating polymer network, the polyol is present in the dry polymer or interpenetrating polymer network in an amount of from about 1 wt.% to about 40 wt.%.

[0256] In one aspect of the polymer or interpenetrating polymer network, the reagent further comprises a third adduct of the first polyfunctional crosslinking agent and a second quaternary ammonium salt where

[0257] R 1a 、R 2a and R 3a are each independently methyl or ethyl;

[0258] A 1 is a linking group selected from the group consisting of: -(C3-C 20 alkylene)-, -(C3-C 20 heteroalkylene)-, -(C6-C 10 arylene)-(C3-C 20 alkylene)-, -(CR m1 R n1 ) x42 -W 42 -(CR p1 R q1 ) y42 - and -(CR m1R n1 ) x43 -W 43 -(CR p1 R q1 ) y43 -, wherein -(C3-C 20 alkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; and -(C3-C 20 alkylene)- and -(C3-C 20 heteroalkylene)- are optionally substituted with 1 to 6 substituents independently selected from the following: -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl);

[0259] Each R m1 、R n1 、R p1 and R q1 is independently selected from H and C1-C4 alkyl;

[0260] W 42 is selected from -C(O)-; -C(O)O-; -OC(O)-; -C(O)NH-; and -NHC(O)-;

[0261] W 43 is selected from 5- to 6-membered cycloalkyl, C6-C 10 aryl, 5- to 6-membered heteroalkyl, and 5- to 6-membered heteroaryl, wherein the heteroalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si; and the heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si;

[0262] x42 is an integer from 1 to 19, and y42 is an integer from 1 to 19, wherein 3 ≤ (x42 + y42) ≤ 20;

[0263] x43 is an integer from 1 to 20, and y43 is an integer from 0 to 19, wherein 3 ≤ (x43 + y43) ≤ 20;

[0264] Y 1 is selected from the group consisting of: -OH, -NHR 4a , -SH, -CO2H, -C(O)NHR 4a , -C(S)NHR 4a ,

[0265]

[0266] Each R 4a is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl), wherein -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si; and

[0267] X - is independently an acetate ion, a halide ion, a sulfate ion, a sulfonate ion, a phosphate ion, a phosphonate ion, a carbonate ion, a silicate ion, a hexafluorophosphate ion, a hexafluoroantimonate ion, a trifluoromethanesulfonate ion, a borate ion, or an organically substituted derivative of any of the foregoing.

[0268] In one aspect of the polymer or interpenetrating polymer network, the reagent further comprises a third adduct of the fourth polyfunctional crosslinking agent and a second quaternary ammonium salt wherein

[0269] R 1a 、R 2a and R 3a are each independently methyl or ethyl;

[0270] A 1 is a linking group selected from the group consisting of: -(C3-C 20 alkylene)-, -(C3-C 20 heteroalkylene)-, -(C6-C 10 arylene)-(C3-C 20 alkylene)-, -(CR m1 R n1 ) x42 -W 42 -(CR p1 R q1 ) y42 - and -(CR m1 R n1 ) x43 -W 43 -(CR p1 R q1 ) y43-, wherein -(C3-C 20 alkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; and -(C3-C 20 alkylene)- and -(C3-C 20 heteroalkylene)- are optionally substituted with 1 to 6 substituents independently selected from: -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl);

[0271] Each R m1 、R n1 、R p1 and R q1 is independently selected from H and C1-C4 alkyl;

[0272] W 42 is selected from -C(O)-; -C(O)O-; -OC(O)-; -C(O)NH-; and -NHC(O)-;

[0273] W 43 is selected from 5- to 6-membered cycloalkyl, C6-C 10 aryl, 5- to 6-membered heteroalkyl, and 5- to 6-membered heteroaryl, wherein the heteroalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si; and the heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si;

[0274] x42 is an integer from 1 to 19, and y42 is an integer from 1 to 19, where 3 ≤ (x42 + y42) ≤ 20;

[0275] x43 is an integer from 1 to 20, and y43 is an integer from 0 to 19, where 3 ≤ (x43 + y43) ≤ 20;

[0276] Y 1 is selected from the group consisting of: -OH, -NHR 4a 、-SH、-CO2H、-C(O)NHR 4a 、-C(S)NHR 4a 、

[0277]

[0278] Each R 4a is independently selected from the group consisting of: H, -(C6-C 10aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl), wherein -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si; and

[0279] X - is independently an acetate ion, a halide ion, a sulfate ion, a sulfonate ion, a phosphate ion, a phosphonate ion, a carbonate ion, a silicate ion, a hexafluorophosphate ion, a hexafluoroantimonate ion, a trifluoromethanesulfonate ion, a borate ion, or an organically substituted derivative of any of the foregoing.

[0280] On the one hand, the fourth multifunctional crosslinking agent is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1 wt.% to about 15 wt.%.

[0281] In one aspect of the polymer or interpenetrating polymer network, the fourth multifunctional crosslinking agent is different from the first multifunctional crosslinking agent, and different from the second multifunctional crosslinking agent when present, and different from the third multifunctional crosslinking agent when present.

[0282] In one aspect of the polymer or interpenetrating polymer network, the fourth multifunctional crosslinking agent is a fourth polyisocyanate.

[0283] In one aspect of the polymer or interpenetrating polymer network, the fourth polyisocyanate is prepared from a diisocyanate selected from the group consisting of: hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), m-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

[0284] In one aspect of the polymer or interpenetrating polymer network, the fourth polyisocyanate is selected from the group consisting of: N-3300, N-100, Z4470SN, T series polyisocyanates and M series polyisocyanates.

[0285] In one aspect of the polymer or interpenetrating polymer network, the second quaternary ammonium salt is (C2DMDEG-Br).

[0286] In one aspect of the polymer or interpenetrating polymer network, the second quaternary ammonium salt is present in the dry polymer or interpenetrating polymer network in an amount of about 1 wt.% to about 15 wt.%.

[0287] In one aspect of the polymer or interpenetrating polymer network, the average isocyanate functionality of the third adduct is 2 to 3.

[0288] In one aspect of the polymer or interpenetrating polymer network, the average isocyanate functionality of the third adduct is about 2.05 to about 2.3.

[0289] In one aspect of the polymer or interpenetrating polymer network, the third adduct is present in the dry polymer or interpenetrating polymer network in an amount of about 2 wt.% to about 30 wt.%.

[0290] In one aspect of the polymer or interpenetrating polymer network, the polyethyleneimine intermediate is present in the dry polymer or interpenetrating polymer network in an amount of about 0.1 wt.% to about 50 wt.%.

[0291] In one aspect of the polymer or interpenetrating polymer network, the polyethyleneimine intermediate comprises an optionally substituted hydroxyalkylene functional group that reacts with the first adduct and, if present, the second polyfunctional crosslinking agent.

[0292] In one aspect of the polymer or interpenetrating polymer network, the hydroxyalkylene functional group is optionally substituted with a C1-C6 alkyl group, and the C1-C6 alkyl group is optionally substituted with a substituent selected from: -N + (R 20 )3X - , -(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl; each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10Aryl: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2 or -OC(O)-(C1-C6 alkyl); and each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and their organically substituted derivatives.

[0293] In one aspect of the polymer or interpenetrating polymer network, the hydroxyalkylene functional group is hydroxyethylene, hydroxypropylene, hydroxybutylene or an oligomer thereof.

[0294] In one aspect of the polymer or interpenetrating polymer network, the polyethyleneimine intermediate comprises the reaction product of reagents comprising polyethyleneimine, a monoepoxide and an alkylating agent, wherein the monoepoxide is optionally substituted with a C1-C6 alkyl group which is optionally substituted with a substituent selected from: -(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with a hydroxyl group, C1-C6 alkoxy, C6-C 10 aryl optionally substituted with a C1-C6 alkyl group, and carboxyl.

[0295] In one aspect of the polymer or interpenetrating polymer network, the monoepoxide is a C1-C6 alkyl epoxide.

[0296] In one aspect of the polymer or interpenetrating polymer network, the C1-C6 alkyl epoxide is selected from the group consisting of propyl epoxide, butyl epoxide and hexyl epoxide.

[0297] In one aspect of the polymer or interpenetrating polymer network, the polyethyleneimine intermediate comprises the reaction product of reagents comprising polyethyleneimine, a monoepoxide and optionally an alkylating agent; the monoepoxide is substituted with -(C1-C6 alkyl)-N + (R 20 )3X - ; each R 20 is independently selected from the group consisting of C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary-substituted N; and C6-C 10Aryl: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2 or -OC(O)-(C1-C6 alkyl); and each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and their organically substituted derivatives.

[0298] In one aspect of the polymer or interpenetrating polymer network, the alkylating agent comprises one or more R 21 -LG, where each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH; and each LG is a leaving group.

[0299] In one aspect of the polymer or interpenetrating polymer network, the alkylating agent is benzyl halide or hexyl halide.

[0300] In one aspect of the polymer or interpenetrating polymer network, the polyethyleneimine intermediate comprises the reaction product of reagents comprising polyethyleneimine and haloalkanol.

[0301] In one aspect of the polymer or interpenetrating polymer network, the haloalkanol is X 30 -(C2-C6 alkylene)-OH, where X 30 is Cl, Br or I.

[0302] In one aspect of the polymer or interpenetrating polymer network, the reagents of the reaction product comprised in the polyethyleneimine intermediate further comprise monoisocyanate.

[0303] In one aspect of the polymer or interpenetrating polymer network, the monoisocyanate comprises one or more R 30 -NCO, where each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1-3 substituents independently selected from: halogen, -SiR a (OR b )(OR cand -(C6-C 10 aryl); and (2) C6-C 10 aryl optionally substituted with 1-3 substituents independently selected from: halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c ); where each R a is independently C1-C6 alkyl; and each R b and each R c is independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3.

[0304] In one aspect of the polymer or interpenetrating polymer network, the monoisocyanate comprises octyl isocyanate, octadecyl isocyanate, or a combination thereof.

[0305] In one aspect of the polymer or interpenetrating polymer network, the molecular weight of the polyethyleneimine is from about 300 Daltons to about 270,000 Daltons.

[0306] In one aspect of the polymer or interpenetrating polymer network, the molecular weight of the polyethyleneimine is from about 10,000 Daltons to about 200,000 Daltons.

[0307] In one aspect of the polymer or interpenetrating polymer network, the molecular weight of the polyethyleneimine is from about 25,000 Daltons to about 120,000 Daltons.

[0308] In one aspect of the polymer or interpenetrating polymer network, the polyethyleneimine is branched.

[0309] In one aspect of the polymer or interpenetrating polymer network, the polyethyleneimine is hyperbranched.

[0310] In one aspect of the polymer or interpenetrating polymer network, the ratio of primary amine:secondary amine:tertiary amine of the polyethyleneimine is from about 1:2:1 to about 1:1:1.

[0311] In one aspect of the polymer or interpenetrating polymer network, the ratio of primary amine:secondary amine:tertiary amine of the polyethyleneimine is about 1:1:0.7.

[0312] In one aspect of the polymer or interpenetrating polymer network, the polyethyleneimine intermediate is selected from

[0313] or a copolymer of two or more thereof, where:

[0314] each Y 3 is independently H or -O-Y2 , wherein each Y 3 is not H;

[0315] Each Y 2 is independently H or –C(O)-NHR 30 , wherein each Y 2 is not -C(O)-NHR 30 ;

[0316] Each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000;

[0317] Z is -(C2-C6 alkylene)-;

[0318] Each R 10 is independently selected from hydrogen; C1-C6 alkyl optionally substituted with substituents selected from the following: -N(R 20 )3, (C6-C 10 aryl), and -(C1-C6 alkoxy), -(C1-C6 alkoxy) optionally substituted with -OH, -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl; and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tert-substituted N; and C6-C 10 aryl optionally substituted with the following: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl);

[0319] Each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from the following: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with -OH;

[0320] Each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1-3 substituents independently selected from the following: halogen, –SiR a (OR b )(OR c ) and -(C6-C10 (aryl); and (2) C6-C optionally substituted with 1-3 substituents independently selected from the following 10 aryl: halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c ); where each R a is independently C1-C6 alkyl; and each R b and each R c is independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3; and

[0321] each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion, and borate ion, and their organically substituted derivatives;

[0322] provided that:

[0323] when R 10 is C1-C6 alkyl optionally substituted with substituents selected from the following, then the polyethyleneimine intermediate is selected from -(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl.

[0324] In one aspect of the polymer or interpenetrating polymer network, the polyethyleneimine intermediate is where each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000.

[0326] In one aspect of the polymer or interpenetrating polymer network, the second adduct has the formula (I):

[0327]

[0328] where:

[0329] each A is independently selected from or a copolymer of any two or more thereof; and the attachment of each A forms a urethane bond;

[0331] each Y3 independently H or -O-Y 2 , wherein each Y 3 is not H;

[0332] each Y 2 is independently H or –C(O)-NHR 30 , wherein each Y 2 is not -C(O)-NHR 30 ;

[0333] each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000;

[0334] Z is -(C2-C6 alkylene)-;

[0335] each R 10 is independently selected from hydrogen; C1-C6 alkyl optionally substituted with substituents selected from: -N(R 20 )3, (C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl; and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted with: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl);

[0336] each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with -OH;

[0337] each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1 to 3 substituents independently selected from: halogen, –SiR a (OR b)(OR c ) and -(C6-C 10 aryl); (2) C6-C 10 aryl optionally substituted with 1-3 substituents independently selected from the following: halogen, -(C1-C6 alkyl), and –SiR a (OR b )(OR c ); and (3) wherein each R a is independently -(C1-C6 alkyl); and each R b and each R c is independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3;

[0338] each R 40 is independently -(C1-C 10 alkylene)- optionally substituted with phenyl or a 3- to 8-membered cycloalkyl ring; and

[0339] each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion, and borate ion, and their organically substituted derivatives;

[0340] provided that:

[0341] when R 10 is C1-C6 alkyl optionally substituted with a substituent selected from the following, then each A is independently selected from -(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl.

[0342] In one aspect of the polymer or interpenetrating polymer network, the second adduct has the formula (II):

[0343]

[0344] wherein:

[0345] each A is independently selected from or a copolymer of any two or more thereof; and the attachment of each A forms a urethane bond;

[0347] each Y 3Independently H or -O-Y 2 , where each Y 3 is not H;

[0348] Each Y 2 is independently H or –C(O)-NHR 30 , where each Y 2 is not -C(O)-NHR 30 ;

[0349] Each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000;

[0350] Z is -(C2-C6 alkylene)-;

[0351] Each R 10 is independently selected from hydrogen; C1-C6 alkyl optionally substituted with substituents selected from: -N(R 20 )3, (C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl; and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted with: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl);

[0352] Each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with -OH;

[0353] Each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1-3 substituents independently selected from: halogen, –SiR a (OR b )(ORc ), and -(C6-C 10 aryl); (2) C6-C optionally substituted with 1-3 substituents independently selected from the following 10 aryl: halogen, -(C1-C6 alkyl), and –SiR a (OR b )(OR c ); and (3) wherein each R a is independently -(C1-C6 alkyl); and each R b and each R c is independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3;

[0354] Each R 40 is independently -(C1-C 10 alkylene)- optionally substituted with phenyl or a 3- to 8-membered cycloalkyl ring; and

[0355] Each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion, and borate ion, and their organically substituted derivatives;

[0356] Provided that:

[0357] When R 10 is C1-C6 alkyl optionally substituted with a substituent selected from the following, then each A is independently selected from -(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl.

[0358] In one aspect of the polymer or interpenetrating polymer network, the second adduct is present in the dry polymer or interpenetrating polymer network in an amount of about 1 wt.% to about 30 wt.%.

[0359] In one aspect of the polymer or interpenetrating polymer network, the reagent for the random polymerization / crosslinking product contained in the polymer or interpenetrating polymer network further comprises a water-soluble polymer.

[0360] In one aspect of the polymer or interpenetrating polymer network, the water-soluble polymer is crosslinked with: (a) the first polyfunctional crosslinking agent as incorporated in the first adduct; (b) when present, the second polyfunctional crosslinking agent as incorporated in the second adduct; (c) when present, the third polyfunctional crosslinking agent; or (d) any combination of two or more of them.

[0361] In one aspect of the polymer or interpenetrating polymer network, the water-soluble polymer is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.5 wt.% to about 15 wt.%.

[0362] In one aspect of the polymer or interpenetrating polymer network, the water-soluble polymer is selected from the group consisting of hydroxyethyl cellulose (HEC), hydroxypropyl cellulose, polyvinyl alcohol, poly(hydroxyethyl methacrylate-co-alkyl methacrylate), poly(hydroxyethyl methacrylate-co-alkyl acrylate), poly(hydroxyethyl acrylate-co-alkyl methacrylate), poly(hydroxyethyl acrylate-co-alkyl acrylate), polyacrylamide, polyethyleneimine intermediate, copolymers of two or more of them, copolymers of one or more of them with polyvinylpyrrolidone poly(glycidyl acrylate) or with poly(glycidyl methacrylate), and combinations or blends of two or more of them.

[0363] In one aspect of the polymer or interpenetrating polymer network, the water-soluble polymer is hydroxyethyl cellulose or a hydrophobically modified derivative thereof.

[0364] In one aspect of the polymer or interpenetrating polymer network, the water-soluble polymer is another polyethyleneimine intermediate.

[0365] In one aspect of the polymer or interpenetrating polymer network, the reagent for the random polymerization / crosslinked product contained in the polymer or interpenetrating polymer network further comprises a chain extender selected from the group consisting of HO-(C n H 2n )-OH and HO-(C n H 2n-2 )-OH or a combination thereof, where n is an integer from 2 to 8.

[0366] In one aspect of the polymer or interpenetrating polymer network, the chain extender is propylene glycol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexanedimethanol or a combination of two or more of them.

[0367] In one aspect of the polymer or interpenetrating polymer network, the chain extender is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.5 wt.% to about 10 wt.%.

[0368] On the one hand, a composition is provided that comprises a polymer or an interpenetrating polymer network as described above.

[0369] On the one hand, an antimicrobial compound is provided, which is selected from the following:

[0370]

[0371] or a copolymer of two or more of them, wherein:

[0372] each Y 3 is independently H or -O-Y 2 where each Y 3 cannot be H;

[0373] each Y 2 is independently H or -C(O)-NHR 30 where each Y 2 cannot be -C(O)-NHR 30 ;

[0374] each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000;

[0375] Z is -(C2-C6 alkylene)-;

[0376] each R 10 is a C1-C6 alkyl substituted by -N + (R 20 )3X - and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted by: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl);

[0377] each R 21 is independently selected from C1-C6 alkyl optionally substituted by substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted by -OH;

[0378] Each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1-3 substituents independently selected from: halogen, –SiR a (OR b )(OR c ) and -(C6-C 10 aryl); and (2) C6-C 10 aryl optionally substituted with 1-3 substituents independently selected from: halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c ); wherein each R a is independently C1-C6 alkyl; and each R b and each R c are independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3; and

[0379] Each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion, and borate ion, and their organically substituted derivatives.

[0380] In one aspect, in the aforementioned antimicrobial compound, each Y 2 is H.

[0381] In one aspect, in the aforementioned antimicrobial compound, the compound is

[0382]

[0383] wherein each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000.

[0384] In one aspect, there is provided a random polymerization product of a polyethyleneimine intermediate and a crosslinking agent, wherein the polyethyleneimine intermediate is selected from:

[0385]

[0386] or a copolymer of two or more thereof, wherein:

[0387] Each Y 3 is independently H or -O-Y 2 wherein each Y 3It cannot be H;

[0388] Each Y 2 is independently H or -C(O)-NHR 30 wherein each Y 2 cannot be -C(O)-NHR 30 ;

[0389] Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000;

[0390] Z is -(C2-C6 alkylene)-;

[0391] Each R 10 is C1-C6 alkyl substituted by -N + (R 20 )3X - and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted by: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl);

[0392] Each R 21 is independently selected from C1-C6 alkyl optionally substituted by substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted by -OH;

[0393] Each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted by 1 to 3 substituents independently selected from: halogen, –SiR a (OR b )(OR c ) and -(C6-C 10 aryl); and (2) C6-C 10 aryl optionally substituted by 1 to 3 substituents independently selected from: halogen, -(C1-C6 alkyl), and -SiR a (OR b )(ORc ); wherein each R a is independently a C1-C6 alkyl group; and each R b and each R c is independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3; and

[0394] each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and their organically substituted derivatives.

[0395] In one aspect of the random polymerization product, the crosslinking agent is a polyisocyanate.

[0396] In one aspect of the random polymerization product, the polyisocyanate is prepared from a diisocyanate independently selected from the group consisting of hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), m-tetramethylxylene diisocyanate (TMXDI) and trimethylhexamethylene diisocyanate (TMDI).

[0397] In one aspect of the random polymerization product, the polyisocyanate is independently selected from the group consisting of: N-3300, N-100, Z4470SN, T series polyisocyanates and M series polyisocyanates.

[0398] In one aspect of the random polymerization product, wherein the random polymerization product has the formula (I):

[0399]

[0400] wherein:

[0401] each A is independently selected from or a copolymer of any two or more thereof; and the attachment of each A forms a urethane bond;

[0403] each Y 3 is independently H or -O-Y 2 wherein each Y 3It cannot be H;

[0404] Each Y 2 is independently H or –C(O)-NHR 30 , where each Y 2 cannot be -C(O)-NHR 30 ;

[0405] Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000;

[0406] Z is -(C2-C6 alkylene)-;

[0407] Each R 10 is C1-C6 alkyl substituted by -N + (R 20 )3X - , and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tert-substituted N; and C6-C 10 aryl optionally substituted by: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl);

[0408] Each R 21 is independently selected from C1-C6 alkyl optionally substituted by substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted by -OH;

[0409] Each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted by 1 to 3 substituents independently selected from: halogen, –SiR a (OR b )(OR c ) and -(C6-C 10 aryl); (2) C6-C 10 aryl optionally substituted by 1 to 3 substituents independently selected from: halogen, -(C1-C6 alkyl), and –SiR a (OR b )(ORc ); and (3) where each R a is independently -(C1-C6 alkyl); and each R b and each R c is independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3;

[0410] Each R 40 is independently -(C1-C 10 alkylene)- optionally substituted with phenyl or a 3- to 8-membered cycloalkyl ring; and

[0411] Each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and their organically substituted derivatives.

[0412] In one aspect of the random polymerization product, wherein the random polymerization product has the formula (II):

[0413]

[0414] wherein:

[0415] Each A is independently selected from

[0416] or a copolymer of any two or more thereof; and the attachment of each A forms a urethane bond;

[0417] Each Y 3 is independently H or -O-Y 2 , where each Y 3 cannot be H;

[0418] Each Y 2 is independently H or –C(O)-NHR 30 , where each Y 2 cannot be -C(O)-NHR 30 ;

[0419] Each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000;

[0420] Z is -(C2-C6 alkylene)-;

[0421] Each R 10 is -N + (R20 ) 3X - Substituted C1-C6 alkyl, and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted with: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl);

[0422] Each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with -OH;

[0423] Each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1 to 3 substituents independently selected from: halogen, –SiR a (OR b )(OR c ) and -(C6-C 10 aryl); (2) C6-C 10 aryl optionally substituted with 1 to 3 substituents independently selected from: halogen, -(C1-C6 alkyl), and –SiR a (OR b )(OR c ); and (3) wherein each R a is independently -(C1-C6 alkyl); and each R b and each R c is independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3;

[0424] Each R 40 is independently -(C1-C 10 alkylene)- optionally substituted with phenyl or a 3- to 8-membered cycloalkyl ring; and

[0425] Each X -Independently selected from the group consisting of: acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and their organically substituted derivatives.

[0426] On the one hand, a composition is provided which comprises an antimicrobial compound as shown above.

[0427] On the one hand, a composition is provided which comprises a random polymerization product as shown above.

[0428] On the one hand, an antimicrobial coating, coating fluid or spraying fluid is provided which comprises the composition shown above.

[0429] On the one hand, a device, equipment, apparatus or fitting is provided which comprises the coating, coating fluid or spraying fluid shown above.

[0430] On the one hand, in the device, equipment, apparatus or fitting, the coating fluid or the spraying fluid is water-soluble or water-dispersible.

[0431] On the one hand, the device, equipment, apparatus or fitting is selected from the group consisting of: filters, air purifiers and masks.

[0432] On the one hand, the device, equipment, apparatus or fitting is selected from the group consisting of: keyboards, keypads, styli, mice, handheld devices, remote controllers, touchscreens, telephones, handheld devices and displays.

[0433] On the one hand, a personal care aid is provided which comprises the coating, coating fluid or spraying fluid shown above.

[0434] In one aspect of the personal care aid, the coating fluid or the spraying fluid is water-soluble or water-dispersible.

[0435] On the one hand, a method for disinfecting a surface is provided, the method comprising applying the composition described above.

[0436] On the one hand, a method for reducing antimicrobial growth on a surface is provided, the method comprising applying the composition described above to the surface.

[0437] On the one hand, a method for preventing antimicrobial growth on a surface is provided, the method comprising applying the composition described above to the surface.

[0438] On the one hand, a method is provided which includes forming a coating solution containing the composition.

[0439] On the one hand, a method of using the composition described above is provided. The use may include, for example, contacting a surface with the composition.

[0440] On the one hand, a method is provided, which comprises providing any one of the following: an antimicrobial coating, a coating fluid or a spraying fluid, each of the antimicrobial coating, the coating fluid or the spraying fluid comprising the composition described above, and applying the antimicrobial coating, the coating fluid or the spraying fluid to a surface.

[0441] On the one hand, a method is provided, which includes guiding the coating solution to a surface and providing a coating on the surface by applying the coating solution to the surface.

[0442] On the one hand, a polymer or an interpenetrating polymer network is provided, which is prepared by:

[0443] (a) Reacting a first polyfunctional crosslinking agent with a first quaternary ammonium salt to form a first adduct;

[0444] (b) Optionally reacting a polyethyleneimine intermediate with a second polyfunctional crosslinking agent to form a second adduct;

[0445] (c) Optionally reacting the first polyfunctional crosslinking agent or a fourth polyfunctional crosslinking agent with a second quaternary ammonium salt to form a third adduct;

[0446] (d) Combining (i) the first adduct, (ii) the polyethyleneimine intermediate or the second adduct, and (iii) when present, the third adduct with an optional polyol and an optional third polyfunctional crosslinking agent to form an oil phase;

[0447] (e) Dissolving a water-soluble polymer in water to form an aqueous phase;

[0448] (f) Combining the oil phase with the aqueous phase to form an oil-in-water emulsion; and

[0449] (g) Applying the emulsion to a surface and drying and curing the emulsion on the surface to form the polymer or interpenetrating polymer network on the surface.

[0450] On the one hand, a blocking agent is added to the oil phase after step (d) but before step (f).

[0451] On the one hand, step (d) further comprises combining (i) the first adduct, (ii) the polyethyleneimine intermediate or the second adduct, and (iii) when present, the third adduct with optionally the polyol and optionally the third polyfunctional crosslinker in an organic solvent or diluent to form the oil phase.

[0452] On the one hand, step (d) further comprises adding a chain extender to the oil phase; or step (e) further comprises adding a chain extender to the aqueous phase; or a combination thereof.

[0453] On the one hand, step (e) further comprises adding a surfactant to the aqueous phase.

[0454] On the one hand, step (e) further comprises adding an antifoaming agent or defoaming agent to the aqueous phase.

[0455] On the one hand, step (e) further comprises adding either a surfactant or an antifoaming agent or defoaming agent to the aqueous phase.

[0456] On the one hand, step (f) further comprises conducting a direct emulsification process, whereby the emulsion is formed by intense shearing and mixing.

[0457] On the one hand, step (f) further comprises conducting a direct emulsification process, whereby the emulsion is formed by sonication.

[0458] On the one hand, step (f) further comprises conducting a phase inversion emulsification process, whereby a water-in-oil emulsion is first prepared and subsequently phase inversion is carried out to form the oil-in-water emulsion.

[0459] On the one hand, the phase inversion is carried out by changing any combination of the phase ratio, temperature, surfactant, solvent, or two or more of them.

[0460] On the other hand, the present technology provides a personal care aid comprising any one of the coatings, coating fluids, or spraying fluids described above. In some embodiments, the coating fluid or the spraying fluid is water-soluble or water-dispersible.

[0461] Other embodiments are also described and cited herein. Detailed Description

[0462] In the following description, for purposes of explanation, numerous specific details are set forth in order to provide a thorough understanding of the present technology. However, it will be apparent that the present technology may be practiced without these specific details. It should be understood that certain aspects, modes, embodiments, variations, and features of the present technology are described below at different levels of detail in order to provide a substantial understanding of the present technology.

[0463] Definitions

[0464] For convenience, the meanings of some terms and phrases used in this specification, the examples, and the appended claims are provided below. Unless otherwise stated or implicit from the context, the following terms and phrases include the meanings provided below. These definitions are provided to assist in describing particular embodiments and are not intended to limit the claimed subject matter, as the scope of the technology is limited only by the claims. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this technology belongs. If there is an obvious deviation in the use of terms in the art from the definitions of such terms provided herein, the definitions provided within this specification shall prevail.

[0465] As used in this specification and the appended claims, unless the context clearly indicates otherwise, the singular forms "a", "an", and "the" include plural referents. For example, reference to "a cell" includes a combination of two or more cells, etc.

[0466] As used herein, the term "about" or "approximately" when referring to a value or parameter means a number that typically includes in either direction (greater than or less than) within a range of 5%, 10%, 15%, or 20% of the stated number, unless otherwise stated or otherwise obvious from the context (unless such a number is less than 0% of the possible value or exceeds 100% of the possible value). As used herein, a reference to "about" or "approximately" a value or parameter includes (and describes) embodiments that relate to the stated value or parameter. For example, a description of "about X" includes a description of "X".

[0467] As used herein, the term "or" means "and / or". In this document, the term "and / or" as used in phrases such as "A and / or B" is intended to include: both A and B; A or B; "A" (alone); and "B" (alone). Similarly, the term "and / or" as used in phrases such as "A, B, and / or C" is intended to cover each of the following embodiments: A, B, and C; A, B, or C; A or C; A or B; B or C; A and C; A and B; B and C; A (alone); B (alone); and C (alone).

[0468] As used herein, the term "comprising" means that other elements may exist in addition to the elements of the defined presentation. The use of "comprising" indicates inclusion rather than limitation.

[0469] The term "consisting of" refers to the compositions, methods, and their corresponding components as described herein, which exclude any element not recited in the description of the embodiment.

[0470] As used herein, the term "consisting essentially of" refers to those elements required for a given embodiment. The term permits the presence of additional elements that do not materially affect the basic and novel or functional characteristics of that embodiment of the technology.

[0471] As used herein, "aryl" refers to a fully aromatic carbocyclic (all-carbon) ring. "Aryl" may consist of two or more fused rings (rings sharing two adjacent carbon atoms). When aryl is a fused-ring system, the ring attached to the remainder of the molecule is fully aromatic. The other rings in the fused-ring system may or may not be fully aromatic. Examples of aryl include, but are not limited to, benzene, naphthalene, and azulene groups.

[0472] As used herein, "alkyl" refers to a straight-chain or branched-chain hydrocarbon group that is fully saturated (no double or triple bonds). The alkyl groups of the presently disclosed compounds can contain from 1 to 15 carbon atoms. The alkyl groups herein can have 1 to 4 carbon atoms, 1 to 5 carbon atoms, 1 to 6 carbon atoms, 1 to 7 carbon atoms, 1 to 8 carbon atoms, 1 to 9 carbon atoms, 1 to 10 carbon atoms, 1 to 11 carbon atoms, 1 to 12 carbon atoms, 1 to 13 carbon atoms, 1 to 14 carbon atoms, or 1 to 15 carbon atoms. As used herein, C1-C6 alkyl represents an alkyl group having 1 to 6 carbon atoms, C1-C4 alkyl represents an alkyl group having 1 to 4 carbon atoms, and C1-C3 alkyl represents an alkyl group having 1 to 3 carbon atoms, and so on. Examples of alkyl include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, tert-pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl.

[0473] As used herein, "alkoxy" refers to an alkyl group as defined above attached to the parent molecular moiety through an oxy group -O-. As used herein, C1-C6 alkoxy represents an alkoxy group containing 1 to 6 carbon atoms, and C1-C3 alkoxy represents an alkoxy group containing 1 to 3 carbon atoms. Representative examples of alkoxy include, but are not limited to, methoxy, ethoxy, propoxy, 2-propoxy, butoxy, tert-butoxy, pentyloxy, hexyloxy, and the like.

[0474] As used herein, "cycloalkyl" refers to, in some embodiments, having from 3 to 14 carbon atoms (e.g., C3-C 14 cycloalkyl), from 3 to 10 carbon atoms (e.g., C3-C 10a monocyclic, bicyclic or polycyclic hydrocarbon ring system having 3 to 12 carbon atoms (e.g., C3-C12 cycloalkyl), or 3 to 8 carbon atoms (e.g., C3-C8 cycloalkyl), or 3 to 6 carbon atoms (e.g., C3-C6 cycloalkyl), or 5 to 6 carbon atoms (e.g., C5-C6 cycloalkyl). The cycloalkyl can be saturated or characterized by one or more points of unsaturation (i.e., carbon-carbon double bonds and / or triple bonds), provided that the points of unsaturation do not give rise to an aromatic system. Examples of monocyclic cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexenyl, cyclohexynyl, cycloheptyl, cycloheptenyl, cycloheptadienyl, cyclooctyl, cyclooctenyl, cyclooctadienyl, etc. The rings of bicyclic and polycyclic cycloalkyl can be fused, bridged or spirocyclic.

[0475] As used herein, unless otherwise specified, "heteroalkyl" refers to an alkyl as defined herein, wherein one or more of the constituent carbon atoms have been replaced by nitrogen, oxygen, sulfur or silicon. A representative example of heteroalkyl is alkoxy. Heteroalkylene is divalent heteroalkyl.

[0476] As used herein, unless otherwise specified, the term "heteroaryl" refers to, in some embodiments, a monocyclic or fused bicyclic aromatic group (or ring) having 5 to 14 (i.e., 5-membered to 14-membered heteroaryl), or 5 to 10 (i.e., 5-membered to 10-membered heteroaryl), or 5 to 6 (i.e., 5-membered to 6-membered heteroaryl) members (i.e., ring vertices), and containing one to five, one to four, one to three, one to two or one heteroatom selected from nitrogen (N), oxygen (O) and sulfur (S). When chemically permissible, the heteroaryl can be attached to the rest of the molecule through a carbon atom or a heteroatom of the heteroaryl. Non-limiting examples of heteroaryl include pyridyl, pyridazinyl, pyrazinyl, pyrimidinyl, triazinyl, purinyl, thienopyridyl, thienopyrimidinyl, pyrazolopyrimidinyl, pyridinopyridyl, imidazopyridine, isothiazolyl, pyrazolyl, indazolyl, pteridinyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiadiazolyl, pyrrolyl, thiazolyl, furyl, thienyl, etc.

[0477] The term "heterocycloalkyl" refers to a non-aromatic monocyclic, bicyclic or polycyclic cycloalkyl ring having 3 to 14 members (e.g., 3- to 14-membered heterocycle), or 3 to 10 members (e.g., 3- to 10-membered heterocycle), or 3 to 8 members (e.g., 3- to 8-membered heterocycle), or 3 to 6 members (e.g., 3- to 6-membered heterocycle), or 5 to 6 members (e.g., 5- to 6-membered heterocycle) in some embodiments, and having one to five, one to four, one to three, one to two or one heteroatom selected from nitrogen (N), oxygen (O), sulfur (S) and silicon (Si). Heterocycloalkyl is saturated or characterized by one or more points of unsaturation (e.g., one or more carbon-carbon double bonds, carbon-carbon triple bonds, carbon-nitrogen double bonds and / or nitrogen-nitrogen double bonds), provided that the points of unsaturation do not give rise to an aromatic system. The rings of bicyclic and polycyclic heterocycloalkyls can be fused, bridged or spiro. Non-limiting examples of heterocycloalkyl include aziridine, ethylene oxide, thioethylene oxide, pyrrolidine, imidazolidine, pyrazolidine, dioxolane, phthalimide, piperidine, 1,4-dioxane, morpholine, thiomorpholine, thiomorpholine-S-oxide, thiomorpholine-S,S-oxide, piperazine, 3,4,5,6-tetrahydropyridazine, tetrahydropyran, pyran, decahydroisoquinoline, 3-pyrroline, thiopyran, tetrahydrofuran, tetrahydrothiophene, quinuclidine, etc. When chemically permissible, heterocycloalkyl can be attached to the remainder of the molecule through a ring carbon atom or a ring heteroatom.

[0478] As used herein, unless otherwise specified, "independently selected" indicates that each specified group of a designated group is independently selected from the subsequent list of species.

[0479] The term "statistically significant" or "significantly" refers to statistical significance and generally means a difference of two standard deviations (2SD) or greater.

[0480] The terms "decrease", "reduced", "reduction" or "inhibit" are all used herein to mean a statistically significant decrease in amount. In some embodiments, "reduce", "reduction" or "decrease" or "inhibit" generally means a decrease of at least 10% compared to a reference level (e.g., in the absence of a given treatment or agent), and can include, for example, a decrease of at least about 10%, at least about 20%, at least about 25%, at least about 30%, at least about 35%, at least about 40%, at least about 45%, at least about 50%, at least about 55%, at least about 60%, at least about 65%, at least about 70%, at least about 75%, at least about 80%, at least about 85%, at least about 90%, at least about 95%, at least about 98%, at least about 99% or more. As used herein, "decrease" or "inhibit" does not cover complete inhibition or reduction compared to the reference level. "Complete inhibition" is 100% inhibition compared to the reference level. The reduction can preferably be to a level acceptable within the normal range of an individual without a given disorder.

[0481] The terms "increased", "increase", "enhance" or "activate" are all used herein to mean a statistically significant increase in amount. In some embodiments, the terms "increased", "increase", "enhance" or "activate" can represent an increase of at least 10% compared to a reference level, such as an increase of at least about 20%, or at least about 30%, or at least about 40%, or at least about 50%, or at least about 60%, or at least about 70%, or at least about 80%, or at least about 90%, or up to and including a 100% increase or any increase from 10 - 100%, or an increase of at least about 2-fold, at least about 3-fold, or at least about 4-fold, at least about 5-fold or at least about 10-fold, or any increase from 2-fold to 10-fold or greater compared to the reference level. In the case of a marker or symptom, "increase" is a statistically significant increase in the level.

[0482] As used herein, the term "polyisocyanate" generally refers to a family of polyisocyanates containing more than one isocyanate-reactive group, such as but not limited to N3300 and N100 (manufactured by Covestro Deutschland AG of Leverkusen, Germany), which are aliphatic polyisocyanates based on HDI (hexamethylene diisocyanate) trimers; Z4470SN (manufactured by Covestro Deutschland AG, Leverkusen, Germany), which are polyfunctional polyisocyanates based on IPDI (isophorone diisocyanate); T series polyisocyanates, which are aromatic polyisocyanates based on toluene diisocyanate (TDI); and M series polyisocyanates, which are aromatic polyisocyanates based on 4,4-diphenylmethane diisocyanate (MDI).

[0483] As used herein, the term "antimicrobial" is generally used to indicate at least a certain degree of microbial killing of a coating on a composition or part of a surface. For example, antimicrobial can be used to indicate biostatic efficacy, a reduction in the sanitizing level (3-log or 99.9%) in at least one organism, or a reduction in the disinfection level (5-log or 99.999%) in at least one organism, or sterilization (no detectable organisms). Microorganisms or microbes can include bacteria, viruses, fungi (including molds and yeasts), microalgae, or spores of any species. Thus, the antimicrobials herein encompass antiviral, antibacterial, antifungal, and anti-algal (e.g., anti-microalgal).

[0484] As used herein, the terms “residual antimicrobial,” “residual self-disinfection,” and “self-decontaminating surface” are used interchangeably to denote a surface that, once coated with an antimicrobial coating composition and the composition has dried to a film on the surface, maintains antimicrobial efficacy for a period of time under specific conditions. The coated surface may maintain residual antimicrobial efficacy indefinitely, or the coating may eventually “wear” and lose its residual antimicrobial efficacy. The antimicrobial coating composition can be used as a contact disinfectant, bacteriostatic material, disinfectant, or sterilant (e.g., as a liquid antimicrobial applied to a contaminated surface), and can also leave a residual antimicrobial coating on the surface after the surface has dried or cured, which can keep inactivating new micro-organisms that will come into contact with the coated surface. In various embodiments, until it has dried or cured on the surface, the coating composition may not be antimicrobial, but is still referred to as an antimicrobial coating composition due to its ability to create a residual antimicrobial coating on the surface. The antimicrobial coating composition for various embodiments can provide a surface with residual antimicrobial efficacy, meaning that micro-organisms that are later inoculated onto the coated surface or otherwise come into contact with the coated surface may experience cell death, destruction, or inactivation. The residual antimicrobial action that the coatings herein may produce is not limited to a particular mechanism of action, and no such theory is proposed. For example, the antimicrobial action measured on the surface may be the result of intracellular mutations, inhibition of certain cellular processes, rupture of the cell wall, or featureless inactivation of the organism, as in the case of a virus. Other antimicrobial actions can include inhibiting the reproduction of the organism or inhibiting the ability of the organism to aggregate into a biofilm.

[0485] As used herein, the term "antimicrobial coating composition" refers to a chemical composition comprising at least one chemical species that is used to create a residual antimicrobial coating on a surface after application of the composition, and then dried, allowed to dry or cured in some manner. The term is also used for liquid compositions that may be used as a germicidal spray (disinfectant or sanitizer) as the composition can go on to dry into an antimicrobial coating. The term also extends to include compositions that can be applied sequentially (e.g., above or below the antimicrobial coating composition) or simultaneously with the application of the antimicrobial coating composition to assist in binding the residual antimicrobial coating to the surface, improving the durability of the overall coating, and / or providing a catalytic effect or some enhancement or synergistic effect with the residual antimicrobial coating containing antimicrobial activity. For simplicity, each composition of a plurality of compositions used sequentially or simultaneously to create an overall residual antimicrobial coating on a portion of a surface is referred to as an "antimicrobial coating composition" even if one or more of the compositions used in the coating composition do not have identifiable antimicrobial activity or the active agent is uncertain. An antimicrobial coating composition can comprise a pure 100% active chemical species or can be a solution or suspension of a single chemical species in a solvent. In other aspects, the composition can comprise a complex mixture of chemicals, some of which can undergo chemical reactions (hydrolysis, self-condensation, etc.) within the composition to produce identifiable or unidentifiable reaction products. For example, monomeric chemical species in an antimicrobial coating composition can partially or fully polymerize or copolymerize prior to the coating process using the composition, such as to produce polymers including homopolymers and copolymers having a molecular weight distribution, comonomer ratio or molecular architecture in solution. In other embodiments, chemical components within the antimicrobial coating composition can undergo chemical reactions, grafting or formation of an interpenetrating network on the surface or interface to which the composition is applied, such as when the composition dries and concentrates on the surface or when the coating composition is cured by various methods. In various embodiments, a solution containing a polymer distribution can further polymerize or cure when dried on a surface, such as to achieve longer chain lengths or form a polymer network. The antimicrobial coating composition for various embodiments can further comprise any number and combination of inert excipients such as solvents, buffers, acids, bases, surfactants, emulsifiers, stabilizers, UV absorbers, thickeners, free radical initiators, fillers, pigments or colorants, catalysts, etc.

[0486] As used herein, the term "homopolymer" has its ordinary meaning in organic chemistry of molecules having repeating and identical monomer units. For simplicity, unless otherwise stated, the term homopolymer herein includes each of the smaller oligomers in smaller oligomers, i.e., dimers, trimers, tetramers, dendrimers, dendritic building blocks, etc. For example, the homopolymer distribution herein may include dimers and above, or trimers and above, as indicated. In some cases, the homopolymer chain length distribution may be well defined and characterized, while in other cases, the distribution may not be characterized at all and may remain unknown. The term copolymer herein includes random copolymers, block copolymers, graft copolymers, interpolymer complexes, interpenetrating networks, etc. and blends thereof.

[0487] As used herein, unless otherwise stated, the term "wt.%" has its ordinary meaning of the weight percentage (%) of a component in a chemical composition, based on the total weight of the composition "as is". For example, "based on the total weight of the composition", an aqueous composition containing 1 wt.% amine is equivalent to a composition containing 99.0 grams of water and 1.0 gram of amine. Unless otherwise stated, the wt.% in a composition indicates the wt.% of the active material. "As is" means the composition as written shows the substances added to the mixing vessel, rather than the substances that may ultimately end up in the mixture after some components react (such as component hydrolysis or polymerization).

[0488] Unless otherwise defined herein, scientific and technical terms used in conjunction with this application shall have the meaning commonly understood by one of ordinary skill in the art to which this disclosure pertains. It should be understood that the technology is not limited to the specific methods, protocols, reagents, etc. described herein and may thus vary. The terms used herein are for the purpose of describing particular embodiments only and are not intended to limit the scope of the technology, which is defined only by the claims. Definitions of common terms in immunology and molecular biology can be found in: The Merck Manual of Diagnosis and Therapy; 3 The Encyclopedia of Molecular Cell Biology and Molecular Medicine; 4 Molecular Biology and Biotechnology: a Comprehensive Desk Reference; 5 Immunology; 6 Janeway's Immunobiology;7 Lewin's Genes XI 8 Molecular Cloning: A Laboratory Manual 9 Basic Methods in Molecular Biology 10 Laboratory Methods in Enzymology 11 Current Protocols in Molecular Biology (CPMB) 12 Current Protocols in Protein Science (CPPS) 13 and Current Protocols in Immunology (CPI). 14

[0489] Other terms are defined within the description of the various aspects of the present technology.

[0490] Antimicrobial coating

[0491] Surfaces of objects that come into direct or indirect contact with humans and animals are exposed to a high microbial load and have a significant impact on the spread of diseases and infections. The antimicrobial coatings of the present technology may be particularly useful because they can be applied to almost any surface and significantly reduce the microbial load. Surfaces that can be treated with antimicrobial coatings include, but are not limited to, internal and external building components such as handrails, fixtures, fixture knobs, pulls, and handles; parts of faucets, personal items, telephones, computers, doorknobs, counters, furniture, walls, ticket machines, high-touch areas (e.g., building lounges, public payment methods, and public transportation), and other hard-to-clean / access areas (such as machinery and HVAC systems) in kitchens, bathrooms, toilets, etc. In addition, these coatings are suitable for medical devices and accessories, implants and instruments, laboratory equipment, factories, water filtration equipment, hospitals, schools / childcare facilities, airports, restaurants, gyms, etc.

[0492] Bacteria of particular concern include, but are not limited to, Staphylococcus aureus (Staph), Escherichia coli (E. coli), Methicillin-Resistant Staphylococcus aureus (MRSA), Vancomycin-Resistant Enterococcus faecalis, and Vancomycin-Resistant Enterobacter aerogenes (VRE). Staphylococci are a group of over 30 strains that can cause many different types of infections, including skin infections, food and blood poisoning. Most strains of E. coli are harmless and are part of the healthy flora in the human gut. However, some strains can cause various diseases, including pneumonia, urinary tract infections, diarrhea, and meningitis. Some strains of E. coli can also cause nausea, vomiting, and fever. MRSA is a bacterium that causes infections in different parts of the body. It is more difficult to treat than most other strains of staphylococci because it is resistant to antibiotics. It can cause severe skin, bloodstream, lung, or urinary tract infections. VRE is a bacterium called Enterococci that has become resistant to many antibiotics, especially vancomycin as the name implies. These bacteria can cause severe infections, especially in people who are already sick, weak, and / or immunocompromised. VRE can cause bloodstream infections (sepsis), urinary tract infections, pneumonia, heart infections (endocarditis), or meningitis.

[0493] Viruses of particular concern include, but are not limited to, influenza A and B viruses, respiratory syncytial virus, adenovirus, rhinovirus, and coronaviruses (229E, HKU1, NL63, OC43, and more recently SARS-CoV-2), because these viruses have been shown to have long survival periods on many surfaces. For example, in a recent airport study, 15 Detection of viral nucleic acids of the pathogen indicated viral surface contamination at multiple sites associated with high contact rates and indicated potential risks in the standard passenger pathways at the airport site. These viruses can cause severe infections, especially in people who are already sick, weak, and / or immunocompromised.

[0494] In the chemical coating industry, a 99.9% reduction percentage of bacteria or viruses is equivalent to a three-order-of-magnitude reduction in microbial risk (i.e., 3 log). However, antimicrobial coatings should meet many physical and chemical requirements to be a fully effective and widely applicable antiviral / antibacterial / antifungal agent and surface coating. These properties include:

[0495] 1. Highly antimicrobial against a broad spectrum of viruses, bacteria, and fungi.

[0496] 2. Very fast acting; kills over 99.9% of viruses within ten minutes or less of contact time and bacteria after overnight exposure.

[0497] 3. Durable; maintains at least 98% of its bacterial or viral killing efficiency after 100 days of storage under environmental conditions or 72 hours of storage at 40°C / 85% RH humidity.

[0498] 4. Non-toxic and non-allergenic based on recognized standard test procedures.

[0499] 5. No material leaching over time or when exposed to typical liquids used for cleaning.

[0500] 6. Clearly colorless and transparent as a surface coating.

[0501] 7. A water-based formulation can be easily applied to a wide range of surfaces and materials by painting, spraying, dipping, or other common application methods.

[0502] 8. A durable surface coating that prevents surface delamination or significant deterioration due to water, alcohol, and common solvents.

[0503] 9. Easy and cost-effective to produce from readily available materials.

[0504] 10. Made from common syntheses that allow for a wide range of chemical variations to fine-tune its properties (i.e., solubility, etc.) for various different applications.

[0505] To the knowledge of the present inventor, there are currently no antimicrobial coatings available that meet most or all of these requirements. Many existing antimicrobial coatings tend to deteriorate over time and fail with repeated contamination.

[0506] Conventional coating products that claim to deliver antibacterial properties include those from the Sherwin Williams Company (Cleveland, Ohio) from Axalta (Philadelphia, PA) AM and Ralguard and SILVERSAN from PPG Industrial Coatings (Pittsburgh, PA) TMHowever, these products typically claim to be 99.9% effective but take over 5 hours to reach their maximum efficiency after application. Additionally, existing solutions tend to degrade over time, such that after recontamination (i.e., repeated exposure to pathogens over long periods, combined with regular environmental exposure and / or scrubbing / cleaning), their active performance drops below 90%. At only 90% protection, bacteria and germs have the ability to grow and respire, eventually multiplying to the extent that existing pathogens on the substrate layer will persist, thereby reducing the efficacy of these coatings.

[0507] It has been reported that antimicrobial polymers have embedded agents, including metals such as silver 16 , but these antimicrobial polymers have encountered the fact that the embedded antimicrobial agents may leach out over time, causing the polymer coating to lose its antimicrobial activity. Additionally, such formulations are not entirely satisfactory as they only result in a 3log reduction, which does not completely inhibit bacterial regrowth. This lack of effectiveness may be due to insufficient silver usage and / or uneven dispersion throughout the composition, such that the distribution of antimicrobial particles within the composition / coating is inconsistent and ultimately ineffective.

[0508] Park et al. (2006) 17 reported antimicrobial active polymers made by reacting polyethyleneimine with hydrophobic long-chain hydrocarbon alkylating agents and then quaternizing by methylation. Although these polymers have antibacterial and antiviral activity as surface coatings, the coatings are not colorless, and they are not durable and are not resistant to contact with water and other common solvents that the surface may frequently come into contact with.

[0509] Many have speculated that the antiviral activity of quaternary ammonium polymers is due to the interaction between the hydrophobic quaternary ammonium groups and the negatively charged membrane of the virus, causing the membrane to rupture, which inactivates microbial bodies such as viruses. In fact, the active ingredient in many commercially available antiviral surface sprays is a low-molecular-weight quaternary ammonium surfactant-like material, which is thought to act through this mechanism but does not form a durable surface coating.

[0510] Researchers have reported that acrylic or methacrylic acid copolymers with quaternary ammonium functional groups have antimicrobial activity 18,19 , but these copolymers do not produce durable water- and solvent-resistant coatings, and some also exhibit a certain level of toxicity.

[0511] Several researchers have reported antimicrobial polyurethane polymers carrying quaternary ammonium functional groups 20,21,22, but these polymers have many drawbacks. Some are water-soluble and thus not suitable for use in durable surface coatings. Others did not report the durability of the test coatings or the toxicity of the materials. Some syntheses are rather cumbersome, requiring some expensive materials and up to four synthetic steps, including amine blocking and de-blocking reactions.

[0512] Gao et al. (2007) 23 reported the synthesis and antibacterial activity of polymers synthesized by alkylation of polyethyleneimine with propyl epoxide and then quaternization with benzyl chloride. These polymers were reported to be highly antibacterial with contact times as short as 4 minutes, but they are water-soluble and thus not suitable for producing durable surface coatings. In addition, there were no reports on the virus and toxicity tests of these polymers.

[0513] Although antimicrobial quaternary compounds and polymers are previously known, simple coatings of these materials are either not optically transparent, not highly antimicrobial, not durable, and the simple step of crosslinking the coating to achieve durability is not sufficient to achieve these properties simultaneously.

[0514] The polymers or interpenetrating polymer networks of the present technology

[0515] The present technology provides water-based quaternary polymer structures and their compositions and formulations that almost meet all of the requirements listed above.

[0516] In one aspect, provided herein is a polymer or interpenetrating polymer network that comprises a random polymerization / crosslinking product of reagents that comprise, consist essentially of, or consist of: (i) a first adduct of a first polyfunctional crosslinker and a first quaternary ammonium salt; (ii) a polyethyleneimine intermediate or a second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinker; and (iii) a water-soluble polymer.

[0517] In another aspect, provided herein is a polymer or interpenetrating polymer network that comprises a random polymerization / crosslinking product of reagents that comprise, consist essentially of, or consist of: (i) a first adduct of a first polyfunctional crosslinker and a first quaternary ammonium salt; and (ii) a polyethyleneimine intermediate or a second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinker.

[0518] On the other hand, the present disclosure provides a polymer or an interpenetrating polymer network comprising a random polymerization / crosslinking product of reagents, said reagents comprising, consisting essentially of, or consisting of: (i) a first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt; (ii) optionally a polyol; (iii) a polyethyleneimine intermediate or a second adduct of said polyethyleneimine intermediate and a second polyfunctional crosslinking agent; (iv) optionally a third polyfunctional crosslinking agent; (v) a water-soluble polymer.

[0519] The water-soluble polymer comprises, consists essentially of, or consists of: hydroxyethyl cellulose, hydroxypropyl cellulose, methyl cellulose, hydrophobically modified cellulose, poly(2-hydroxyethyl methacrylate-co-alkyl methacrylate), poly(2-hydroxyethyl acrylate-co-alkyl acrylate), poly(2-hydroxyethyl acrylate-co-alkyl methacrylate), poly(2-hydroxyethyl acrylate-co-alkyl acrylate), polyethyleneimine, polyacrylamide, or a modified polymer or copolymer on its side chain or main chain (e.g., modification providing reactive functional groups, hydrophobicity, and / or surface activity), or a combination or blend of two or more thereof, or a copolymer of two or more thereof, or a copolymer of one or more thereof with polyvinylpyrrolidone, poly(glycidyl acrylate), or with poly(glycidyl methacrylate).

[0520] The water-soluble polymer may be present in the dry polymer or interpenetrating polymer network in an amount of from about 0.5 wt.% to about 15 wt.%. This includes about 0.5 wt.%, 0.75 wt.%, 1 wt.%, 1.5 wt.%, 2 wt.%, 2.5 wt.%, 3 wt.%, 3.5 wt.%, 4 wt.%, 4.5 wt.%, 5 wt.%, 5.5 wt.%, 6 wt.%, 6.5 wt.%, 7 wt.%, 7.5 wt.%, 8 wt.%, 8.5 wt.%, 9 wt.%, 9.5 wt.%, 10 wt.%, 10.5 wt.%, 11 wt.%, 11.5 wt.%, 12 wt.%, 12.5 wt.%, 13 wt.%, 13.5 wt.%, 14 wt.%, 14.5 wt.%, or 15 wt.%, or any value therebetween. In some embodiments, the water-soluble polymer is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.5 wt.% to about 15 wt.%, from about 3 wt.% to about 12 wt.%, or from about 5 wt.% to about 10 wt.%.

[0521] On the other hand, the present invention provides a polymer or an interpenetrating polymer network comprising a random polymerization / crosslinking product of reagents, said reagents comprising, consisting essentially of, or consisting of: (i) a first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt; (ii) optionally a polyol; (iii) a polyethyleneimine intermediate or a second adduct of said polyethyleneimine intermediate and a second polyfunctional crosslinking agent; and (iv) optionally a third polyfunctional crosslinking agent.

[0522] The first quaternary ammonium salt may have the following chemical structure:

[0523]

[0524] Wherein:

[0525] R 1 is selected from the group consisting of: -(C8-C 30 alkyl), -(C8-C 30 heteroalkyl), -(C8-C 30 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl), -(C6-C 10 aryl)-(C8-C 30 alkyl), -(C6-C 10 aryl)-(C8-C 30 heteroalkyl), -(CR m R n ) x10 -W 10 -(CR p R q ) y10 -H and -(CR m R n ) x11 -W 11 -(CR p R q ) y11 H-; wherein -(C8-C 30 heteroalkyl), -(C8-C 30 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl)-(C8-C 30 heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S, and Si;

[0526] R 2 is selected from the group consisting of: -(C1-C4 alkyl), -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl), -(C6-C10 aryl), -(C6-C 10 aryl)-(C1-C4 alkyl), -(C6-C 10 aryl)-(C1-C4 heteroalkyl); -(CR m R n ) x20 -W 20 -(CR p R q ) y20 -H and -(CR m R n ) x21 -W 21 -(CR p R q ) y21 -H; wherein -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl)-(C1-C4 heteroalkyl) have 1 to 2 heteroatoms independently selected from O, S, and Si;

[0527] R 3 is selected from the group consisting of: -(C1-C 30 alkyl), -(C1-C 30 heteroalkyl), -(C1-C 30 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl), -(C6-C 10 aryl)-(C1-C 30 alkyl), -(C6-C 10 aryl)-(C1-C 30 heteroalkyl), -(CR m R n ) x30 -W 30 -(CR p R q ) y30 -H and -(CR m R n ) x31 -W 31 -(CR p R q ) y31 -H; wherein -(C1-C 30 heteroalkyl), -(C1-C 30 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl)-(C1-C 30heteroalkyl) having 1 to 4 heteroatoms independently selected from O, S and Si;

[0528] A is a linking group selected from the group consisting of: -(C3-C 20 Alkylene)-, -(C3-C 20 Heteroalkylene)-, -(C6-C 10 Arylene)-(C3-C 20 Alkylene), -(CR m R n ) x40 -W 40 -(CR p R q ) y40 -and-(CR m R n ) x41 -W 41 -(CR p R q ) y41 -, where -(C3-C 20 -(C3-C 20 Alkylene)- and -(C3-C 20 optionally substituted by 1 to 6 substituents independently selected from the following: -(C6-C 10 Aryl)-(C1-C3 alkyl), -(C6-C 10 Aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 Aryl), -(C1-C3 heteroalkyl)-(C6-C 10 Aryl) and -(C6-C 10 Aryl);

[0529] Each R m , R n , R p and R q Independently selected from H and C1-C4 alkyl;

[0530] W 10 , W 20 , W 30 and W 40 independently selected from -C(O)-; -C(O)O-; -OC(O)-; -C(O)NH-; and -NHC(O)-;

[0531] W 11 , W 21 , W 31 and W 41 independently selected from 5- to 6-membered cycloalkyl, C6-C10 Aryl, 5- to 6-membered heteroalkyl, and 5- to 6-membered heteroaryl, wherein the heteroalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si; and the heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si;

[0532] x10 is an integer from 1 to 30, and y10 is an integer from 0 to 29, where 8 ≤ (x10 + y10) ≤ 30;

[0533] x11 is an integer from 1 to 30, and y11 is an integer from 0 to 29, where 8 ≤ (x11 + y11) ≤ 30;

[0534] x20 is an integer from 1 to 4, and y20 is an integer from 0 to 3, where x20 + y20 ≤ 4;

[0535] x21 is an integer from 1 to 4, and y21 is an integer from 0 to 3, where x21 + y21 ≤ 4;

[0536] x30 is an integer from 1 to 30, and y30 is an integer from 0 to 29, where x30 + y30 ≤ 30;

[0537] x31 is an integer from 1 to 30, and y31 is an integer from 0 to 29, where x31 + y31 ≤ 30;

[0538] x40 is an integer from 1 to 19, and y40 is an integer from 1 to 19, where 3 ≤ (x40 + y40) ≤ 20;

[0539] x41 is an integer from 1 to 20, and y41 is an integer from 0 to 19, where 3 ≤ (x41 + y41) ≤ 20;

[0540] Y is selected from the group consisting of: -OH, -NHR 4 , -SH, -CO2H, -C(O)NHR 4 , -C(S)NHR 4 ,

[0541]

[0542] Each R 4 is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl), where -(C6-C10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si; and

[0543] X - is independently an acetate ion, a halide ion, a sulfate ion, a sulfonate ion, a phosphate ion, a phosphonate ion, a carbonate ion, a silicate ion, a hexafluorophosphate ion, a hexafluoroantimonate ion, a trifluoromethanesulfonate ion, a borate ion, or an organically substituted derivative of any of the foregoing.

[0544] In some embodiments, R 1 is selected from the group consisting of: -(C 12 -C 30 alkyl), -(C 12 -C 30 heteroalkyl), -(C 12 -C 30 alkyl)-(C6-C 10 aryl), -(C 12 -C 30 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl)-(C 12 -C 30 alkyl) and -(C6-C 10 aryl)-(C 12 -C 30 heteroalkyl); wherein -(C 12 -C 30 heteroalkyl), -(C 12 -C 30 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl)-(C 12 -C 30 heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 1 is -(C 12 -C 30 alkyl). In some embodiments, R 1 is -(C8-C 30 heteroalkyl), which has 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 1 is -(C6-C 10 aryl)-(C 12 -C 30 alkyl). In some embodiments, R 1 is -(C 12-C 30 -alkyl)-(C6-C 10 aryl). In some embodiments, R 1 is -(C6-C 10 aryl)-(C 12 -C 30 heteroalkyl) having 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 1 is -(C 12 -C 30 heteroalkyl)-(C6-C 10 aryl) having 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 1 is -(CR m R n ) x10 -W 10 -(CR p R q ) y10 -H. In some embodiments, R 1 is -(CR m R n ) x11 -W 11 -(CR p R q ) y11 -H.

[0545] In some embodiments, R 2 is -(C1-C4 alkyl). In some embodiments, R 2 is -(C1-C4 heteroalkyl) having 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 2 is -(C6-C 10 aryl)-(C1-C4 alkyl). In some embodiments, R 2 is -(C1-C4 alkyl)-(C6-C 10 aryl). In some embodiments, R 2 is -(C6-C 10 aryl). In some embodiments, R 2 is -(C6-C 10 aryl)-(C1-C4 heteroalkyl) having 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 2 is -(C1-C4 heteroalkyl)-(C6-C 10 aryl) having 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 2 is -(CR m R n) x20 -W 20 -(CR p R q ) y20 -H. In some embodiments, R 2 is -(CR m R n ) x21 -W 21 -(CR p R q ) y21 -H.

[0546] In some embodiments, R 3 is selected from the group consisting of: -(C1-C4 alkyl), -(C1-C4 heteroalkyl), -(C1-C4 alkyl)-(C6-C 10 aryl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl)-(C1-C4 alkyl), and -(C6-C 10 aryl)-(C1-C4 heteroalkyl); wherein -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl)-(C1-C4 heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 3 is -(C1-C4 alkyl). In some embodiments, R 3 is -(C1-C4 heteroalkyl) having 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 3 is -(C6-C 10 aryl)-(C1-C4 alkyl). In some embodiments, R 3 is -(C1-C4 alkyl)-(C6-C 10 aryl). In some embodiments, R 3 is -(C6-C 10 aryl)-(C1-C4 heteroalkyl) having 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 3 is -(C1-C4 heteroalkyl)-(C6-C 10 aryl) having 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 3 is -(CR m R n ) x30 -W 30 -(CR p Rq ) y30 -H. In some embodiments, R 3 is -(CR m R n ) x31 -W 31 -(CR p R q ) y31 -H.

[0547] In some embodiments, R 2 and R 3 are methyl. In some embodiments, R 1 is C 12 -C 30 alkyl, and R 2 and R 3 are methyl.

[0548] In some embodiments, A is -(C3-C 20 alkylene) optionally substituted with 1 to 6 substituents independently selected from: -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl). In some embodiments, A is -(C3-C 20 heteroalkylene) having 1 to 4 heteroatoms independently selected from O, S, and Si, and optionally substituted with 1 to 6 substituents independently selected from: -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl). In some embodiments, A is -(C6-C 10 arylene)-(C3-C 20 alkylene)-. In some embodiments, A is -(C3-C 20 alkylene)-(C6-C 10 arylene)-.

[0549] In some embodiments, A is -(CR m R n ) x40 -W40 -(CR p R q ) y40 -. In some embodiments, A is -(CR m R n ) x41 -W 41 -(CR p R q ) y41 -.

[0550] In some embodiments, A is -(CH2) m - or -(CH2CHR 5 -O-) n CH2CHR 5 -, where m is an integer from 2 to 20; n is 0, 1, 2, 3, 4 or 5; and each R 5 is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl), wherein -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S and Si. In some embodiments, R 5 is H or methyl.

[0551] In some embodiments, Y is -OH. In some embodiments, Y is -NHR 4 . In some embodiments, Y is -SH. In some embodiments, Y is -CO2H. In some embodiments, Y is -C(O)NHR 4 , where R 4 is selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl), wherein -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C10 The aryl group has 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, Y is -C(S)NHR 4 , where R 4 is selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl), where -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, Y is where each R 4 is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl), where -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, Y is where each R 4 is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl), where -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si.

[0552] X -It can be independently selected from the group consisting of: acetate ion, halide ion (e.g., chloride ion, bromide ion or iodide ion), sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and their organically substituted derivatives. As used herein, unless otherwise specified, "organically substituted derivative" refers to an anion in which a sulfur atom, a phosphorus atom, a boron atom, a silicon atom or a carbonyl group is substituted by an alkyl or aryl group. Non-limiting examples include methyl sulfate, methanesulfonate, p-toluenesulfonate, trifluoromethanesulfonate and trifluoroacetate.

[0553] In some embodiments, the first quaternary ammonium salt is

[0554]

[0555] or a combination of two or more thereof.

[0556] The first quaternary ammonium salt can be present in the dry polymer or interpenetrating polymer network in an amount of about 1 wt.% to about 50 wt.%. This includes about 1 wt.%, 2 wt.%, 3 wt.%, 4 wt.%, 5 wt.%, 6 wt.%, 7 wt.%, 8 wt.%, 9 wt.%, 10 wt.%, 11 wt.%, 12 wt.%, 13 wt.%, 14 wt.%, 15 wt.%, 16 wt.%, 17 wt.%, 18 wt.%, 19 wt.%, 20 wt.%, 21 wt.%, 22 wt.%, 23 wt.%, 24 wt.%, 25 wt.%, 26 wt.%, 27 wt.%, 28 wt.%, 29 wt.%, 30 wt.%, 31 wt.%, 32 wt.%, 33 wt.%, 34 wt.%, 35 wt.%, 36 wt.%, 37 wt.%, 38 wt.%, 39 wt.%, 40 wt.%, 41 wt.%, 42 wt.%, 43 wt.%, 44 wt.%, 45 wt.%, 46 wt.%, 47 wt.%, 48 wt.%, 49 wt.% or 50 wt.% or any value therebetween. In some embodiments, the first quaternary ammonium salt is present in the dry polymer or interpenetrating polymer network in an amount of about 5 wt.% to about 25 wt.%. More precisely, the amount of the quaternary ammonium salt can be expressed in milliequivalents / g (mN / g), rather than wt.% based on the total weight of the dry polymer or interpenetrating polymer network. The first quaternary ammonium salt can be present in the dry polymer or interpenetrating polymer network in an amount of about 0.1 mN / g to about 1.0 mN / g. This includes 0.1 mN / g, 0.2 mN / g, 0.3 mN / g, 0.4 mN / g, 0.5 mN / g, 0.6 mN / g, 0.7 mN / g, 0.8 mN / g, 0.9 mN / g or 1.0 mN / g or any value therebetween. In some embodiments, the first quaternary ammonium salt is present in the dry polymer or interpenetrating polymer network in an amount of about 0.4 mN / g to about 0.9 mN / g. In some embodiments, the first quaternary ammonium salt is present in the dry polymer or interpenetrating polymer network in an amount of about 0.5 mN / g to about 0.8 mN / g.

[0557] The first polyfunctional crosslinking agent can be a first polyisocyanate. In some embodiments, the average isocyanate functionality of the first polyisocyanate is from 2 to 5. This includes an average isocyanate functionality of 2, 3, 4 or 5. In some embodiments, the average isocyanate functionality of the first polyisocyanate is from 3 to 4.

[0558] The second polyfunctional crosslinking agent can be a second polyisocyanate. In some embodiments, the average isocyanate functionality of the second polyisocyanate is from 2 to 5. This includes an average isocyanate functionality of 2, 3, 4 or 5. In some embodiments, the average isocyanate functionality of the second polyisocyanate is from 3 to 4.

[0559] The third polyfunctional crosslinking agent may be a third polyisocyanate. In some embodiments, the average isocyanate functionality of the third polyisocyanate is from 2 to 5. This includes an average isocyanate functionality of 2, 3, 4, or 5. In some embodiments, the average isocyanate functionality of the third polyisocyanate is from 3 to 4.

[0560] In some embodiments, the first polyfunctional crosslinking agent is a first polyisocyanate; the second polyfunctional crosslinking agent, when present, is a second polyisocyanate; the third polyfunctional crosslinking agent, when present, is a third polyisocyanate; wherein the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate are different. In some embodiments, the first polyfunctional crosslinking agent is a first polyisocyanate; the second polyfunctional crosslinking agent, when present, is a second polyisocyanate; the third polyfunctional crosslinking agent, when present, is a third polyisocyanate; wherein the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate are the same.

[0561] Each of the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate may be prepared from a diisocyanate independently selected from the group consisting of: hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), m-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

[0562] In some embodiments, each of the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate is independently selected from the group consisting of: N-3300, N-100, Z4470SN, T series polyisocyanates, and M series polyisocyanates. N-3300 and N-100 are aliphatic polyisocyanates based on HDI (hexamethylene diisocyanate) trimers. Z4470SN is a polyfunctional polyisocyanate based on IPDI (isophorone diisocyanate). T series polyisocyanates are aromatic polyisocyanates based on toluene diisocyanate (TDI). M series polyisocyanates are aromatic polyisocyanates based on 4,4-diphenylmethane diisocyanate (MDI).

[0563] The first multifunctional crosslinking agent may be present in the dry polymer or interpenetrating polymer network in an amount of from about 2 wt.% to about 25 wt.%. This includes 2 wt.%, 3 wt.%, 4 wt.%, 5 wt.%, 6 wt.%, 7 wt.%, 8 wt.%, 9 wt.%, 10 wt.%, 11 wt.%, 12 wt.%, 13 wt.%, 14 wt.%, 15 wt.%, 16 wt.%, 17 wt.%, 18 wt.%, 19 wt.%, 20 wt.%, 21 wt.%, 22 wt.%, 23 wt.%, 24 wt.% or 25 wt.% or any value therebetween. In some embodiments, the first multifunctional crosslinking agent is present in the dry polymer or interpenetrating polymer network in an amount of from about 7 wt.% to about 15 wt.% or from about 5 wt.% to about 20 wt.%.

[0564] The second multifunctional crosslinking agent may be present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1 wt.% to about 10 wt.%, which includes 0.1 wt.%, 0.25 wt.%, 0.5 wt.%, 0.75 wt.%, 1 wt.%, 1.5 wt.%, 2 wt.%, 2.5 wt.%, 3 wt.%, 3.5 wt.%, 4 wt.%, 4.5 wt.%, 5 wt.%, 5.5 wt.%, 6 wt.%, 6.5 wt.%, 7 wt.%, 7.5 wt.%, 8 wt.%, 8.5 wt.%, 9 wt.%, 9.5 wt.% or 10 wt.% or any value therebetween. In some embodiments, the second multifunctional crosslinking agent is present in the dry polymer or interpenetrating polymer network in an amount of from about 1 wt.% to about 10 wt.%, from about 2 wt.% to about 8 wt.% or from about 3 wt.% to about 6 wt.%.

[0565] The third polyfunctional crosslinking agent may be present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1 wt.% to about 20 wt.%. This includes 0.1 wt.%, 0.25 wt.%, 0.5 wt.%, 0.75 wt.%, 1 wt.%, 1.5 wt.%, 2 wt.%, 2.5 wt.%, 3 wt.%, 3.5 wt.%, 4 wt.%, 4.5 wt.%, 5 wt.%, 5.5 wt.%, 6 wt.%, 6.5 wt.%, 7 wt.%, 7.5 wt.%, 8 wt.%, 8.5 wt.%, 9 wt.%, 9.5 wt.%, 10 wt.%, 10.5 wt.%, 11 wt.%, 11.5 wt.%, 12 wt.%, 12.5 wt.%, 13 wt.%, 13.5 wt.%, 14 wt.%, 14.5 wt.%, 15 wt.%, 15.5 wt.%, 16 wt.%, 16.5 wt.%, 17 wt.%, 17.5 wt.%, 18 wt.%, 18.5 wt.%, 19 wt.%, 19.5 wt.% or 20 wt.% or any value therebetween. In some embodiments, the third polyfunctional crosslinking agent is present in the dry polymer or interpenetrating polymer network in an amount of from about 1 wt.% to about 20 wt.% or from about 2 wt.% to about 15 wt.%.

[0566] In some embodiments, the average isocyanate functionality of the first adduct is from 2 to 3. In some embodiments, the average isocyanate functionality of the first adduct is from about 2.05 to about 2.3.

[0567] The first adduct may be present in the dry polymer or interpenetrating polymer network in an amount of from about 5 wt.% to about 70 wt.%. This includes about 5 wt.%, 6 wt.%, 7 wt.%, 8 wt.%, 9 wt.%, 10 wt.%, 11 wt.%, 12 wt.%, 13 wt.%, 14 wt.%, 15 wt.%, 16 wt.%, 17 wt.%, 18 wt.%, 19 wt.%, 20 wt.%, 21 wt.%, 22 wt.%, 23 wt.%, 24 wt.%, 25 wt.%, 26 wt.%, 27 wt.%, 28 wt.%, 29 wt.%, 30 wt.%, 31 wt.%, 32 wt.%, 33 wt.%, 34 wt.%, 35 wt.%, 36 wt.%, 37 wt.%, 38 wt.%, 39 wt.%, 40 wt.%, 41 wt.%, 42 wt.%, 43 wt.%, 44 wt.%, 45 wt.%, 46 wt.%, 47 wt.%, 48 wt.%, 49 wt.%, 50 wt.%, 51 wt.%, 52 wt.%, 53 wt.%, 54 wt.%, 55 wt.%, 56 wt.%, 57 wt.%, 58 wt.%, 59 wt.%, 60 wt.%, 61 wt.%, 62 wt.%, 63 wt.%, 64 wt.%, 65 wt.%, 66 wt.%, 67 wt.%, 68 wt.%, 69 wt.% or 70 wt.% or any value therebetween. In some embodiments, the first adduct is present in the dry polymer or interpenetrating polymer network in an amount of from about 10 wt.% to about 50 wt.%, from about 15 wt.% to about 65 wt.%, from about 15 wt.% to about 60 wt.%, from about 15 wt.% to about 50 wt.%, from about 20 wt.% to about 70 wt.%, from about 20 wt.% to about 60 wt.% or from about 20 wt.% to about 50 wt.%.

[0568] The polyol may be present in the dry polymer or interpenetrating polymer network in an amount of from about 1 wt.% to about 40 wt.%. This includes 1 wt.%, 2 wt.%, 3 wt.%, 4 wt.%, 5 wt.%, 6 wt.%, 7 wt.%, 8 wt.%, 9 wt.%, 10 wt.%, 11 wt.%, 12 wt.%, 13 wt.%, 14 wt.%, 15 wt.%, 16 wt.%, 17 wt.%, 18 wt.%, 19 wt.%, 20 wt.%, 21 wt.%, 22 wt.%, 23 wt.%, 24 wt.%, 25 wt.%, 26 wt.%, 27 wt.%, 28 wt.%, 29 wt.%, 30 wt.%, 31 wt.%, 32 wt.%, 33 wt.%, 34 wt.%, 35 wt.%, 36 wt.%, 37 wt.%, 38 wt.%, 39 wt.% or 40 wt.% or any value therebetween. In some embodiments, the polyol is present in the dry polymer or interpenetrating polymer network in an amount of from about 5 wt.% to about 25 wt.%.

[0569] In some embodiments, the polyol may be selected from the group consisting of: polyether polyols, polyester polyols, polyacrylic polyols, polymethacrylic polyols, polycaprolactone polyols, polybutadiene polyols, poly(acrylonitrile-co-butadiene) polyols, polysiloxane polyols, copolymers of any two or more thereof, and combinations of any two or more thereof.

[0570] In some embodiments, the polyol comprises, consists essentially of, or consists of: polytetramethylene glycol (PTMG), polyethylene glycol (PEG), polypropylene glycol (PPG), or combinations of two or more thereof, or copolymers of one or more thereof with polyester, polycaprolactone, polybutadiene, poly(acrylonitrile-butadiene), polysiloxane, or polyacrylate. In some embodiments, the polyol is selected from the group consisting of: poly(tetramethylene glycol), polyethylene glycol, polypropylene glycol, poly(ethylene glycol-b-propylene glycol-b-ethylene glycol), and poly(propylene glycol-b-polyethylene glycol-b-propylene glycol).

[0571] In some embodiments, the polyol comprises, consists essentially of, or consists of: polyether polyols, polyester polyols, or combinations thereof.

[0572] The average molecular weight of the polyol can be from about 300 Daltons to about 3000 Daltons. This includes about 200 Daltons, 250 Daltons, 300 Daltons, 350 Daltons, 400 Daltons, 450 Daltons, 500 Daltons, 550 Daltons, 600 Daltons, 650 Daltons, 700 Daltons, 750 Daltons, 800 Daltons, 850 Daltons, 900 Daltons, 950 Daltons, 1000 Daltons, 1050 Daltons, 1100 Daltons, 1150 Daltons, 1200 Daltons, 1250 Daltons, 1300 Daltons, 1350 Daltons, 1400 Daltons, 1450 Daltons, 1500 Daltons, 1550 Daltons, 1600 Daltons, 1650 Daltons, 1700 Daltons, 1750 Daltons, 1800 Daltons, 1850 Daltons, 1900 Daltons, 1950 Daltons or 2000 Daltons or any value therebetween. In some embodiments, the average molecular weight of the polyol is from about 400 Daltons to about 2000 Daltons or from about 600 Daltons to about 1500 Daltons.

[0573] In some embodiments, the polyol is pre-reacted with a first polyisocyanate to form an isocyanate-terminated prepolymer. In some embodiments, the polyol is pre-reacted with a third polyisocyanate to form an isocyanate-terminated prepolymer.

[0574] In some embodiments, the polyethyleneimine intermediate comprises an optionally substituted hydroxyalkylene functional group that reacts with the first adduct and, if present, a second polyfunctional crosslinker. In some embodiments, the polyethyleneimine intermediate comprises an optionally substituted hydroxyalkylene functional group that reacts with the first adduct and, if present, a second polyfunctional crosslinker, and, if present, a third polyfunctional crosslinker.

[0575] In some embodiments, the hydroxyalkylene functional group is optionally substituted with a C1-C6 alkyl group, and the C1-C6 alkyl group is optionally substituted with a substituent selected from: -N + (R 20 )3X - 、-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl; each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C optionally substituted with the following10 Aryl: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2 or -OC(O)-(C1-C6 alkyl); and each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and organically substituted derivatives thereof. In some embodiments, the hydroxyalkylene functional group is substituted with a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with -N + (R 20 )3X - where each R 20 is independently selected from the group consisting of C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary substituted N; and C6-C 10 aryl optionally substituted with: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2 or -OC(O)-(C1-C6 alkyl); and each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and organically substituted derivatives thereof. In some embodiments, the hydroxyalkylene functional group is substituted with –(CH2)-N + (Me)3Cl - . In some embodiments, the hydroxyalkylene functional group is hydroxyethylene, hydroxypropylene, hydroxybutylene or an oligomer thereof.

[0576] In some embodiments, the polyethyleneimine intermediate comprises the reaction product of reagents comprising polyethyleneimine, a monoepoxide and an alkylating agent, wherein the monoepoxide is optionally substituted with a C1-C6 alkyl group, and the C1-C6 alkyl group is optionally substituted with a substituent selected from: -(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with a hydroxyl group, C1-C6 alkoxy, C6-C 10 aryl optionally substituted with a C1-C6 alkyl group, and carboxyl.

[0577] In some embodiments, the monoepoxide is a C1-C6 alkyl epoxide. In some embodiments, the C1-C6 alkyl epoxide is selected from the group consisting of propyl epoxide, butyl epoxide, and hexyl epoxide. In some embodiments, the C1-C6 alkyl epoxide is propyl epoxide. In some embodiments, the C1-C6 alkyl epoxide is butyl epoxide. In some embodiments, the C1-C6 alkyl epoxide is hexyl epoxide.

[0578] In some embodiments, the polyethyleneimine intermediate comprises the reaction product of reagents comprising polyethyleneimine, a monoepoxide, and optionally an alkylating agent; the monoepoxide is substituted by -(C1-C6 alkyl)-N + (R 20 )3X - ; each R 20 is independently selected from the group consisting of C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted with -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl); and each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion, and borate ion, and organically substituted derivatives thereof.

[0579] In some embodiments, the polyethyleneimine intermediate comprises the reaction product of reagents comprising polyethyleneimine and a monoepoxide; the monoepoxide is substituted by -(C1-C6 alkyl)-N + (R 20 )3X - ; each R 20 is independently selected from the group consisting of C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10Aryl: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2 or -OC(O)-(C1-C6 alkyl); and each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and their organically substituted derivatives.

[0580] In some embodiments, the alkylating agent comprises one or more R 21 -LG, wherein each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH; and each LG is a leaving group. As used herein, unless otherwise specified, the leaving group can be a halide ion, a sulfonate ion, etc. In some embodiments, the alkylating agent is a benzyl halide or a hexyl halide.

[0581] In some embodiments, the polyethyleneimine intermediate comprises the reaction product of reagents comprising polyethyleneimine and a haloalkanol. In some embodiments, the haloalkanol is X 30 -(C2-C6 alkylene)-OH, wherein X 30 is Cl, Br or I.

[0582] In some embodiments, the reagents of the reaction product comprised in the polyethyleneimine intermediate further comprise a monoisocyanate. In some embodiments, the monoisocyanate comprises one or more R 30 -NCO, wherein each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1-3 substituents independently selected from: halogen, -SiR a (OR b )(OR c ) and -(C6-C 10 aryl); and (2) C6-C 10 aryl optionally substituted with 1-3 substituents independently selected from: halogen, -(C1-C6 alkyl) and -SiR a (OR b )(OR c); wherein each R a is independently a C1-C6 alkyl group; and each R b and each R c is independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3. In some embodiments, the monoisocyanate comprises octyl isocyanate, octadecyl isocyanate, or a combination thereof.

[0583] The polyethyleneimine intermediate can be present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1 wt.% to about 50 wt.%. This includes 0.1 wt.%, 0.25 wt.%, 0.5 wt.%, 0.75 wt.%, 1 wt.%, 1.5 wt.%, 2 wt.%, 2.5 wt.%, 3 wt.%, 3.5 wt.%, 4 wt.%, 4.5 wt.%, 5 wt.%, 5.5 wt.%, 6 wt.%, 6.5 wt.%, 7 wt.%, 7.5 wt.%, 8 wt.%, 8.5 wt.%, 9 wt.%, 9.5 wt.%, 10 wt.%, 10.5 wt.%, 11 wt.%, 11.5 wt.%, 12 wt.%, 12.5 wt.%, 13 wt.%, 13.5 wt.%, 14 wt.%, 14.5 wt.%, 15 wt.%, 15.5 wt.%, 16 wt.%, 16.5 wt.%, 17 wt.%, 17.5 wt.%, 18 wt.%, 18.5 wt.%, 19 wt.%, 19.5 wt.%, 20 wt.%, 21 wt.%, 22 wt.%, 23 wt.%, 24 wt.%, 25 wt.%, 26 wt.%, 27 wt.%, 28 wt.%, 29 wt.%, 30 wt.%, 31 wt.%, 32 wt.%, 33 wt.%, 34 wt.%, 35 wt.%, 36 wt.%, 37 wt.%, 38 wt.%, 39 wt.%, 40 wt.%, 41 wt.%, 42 wt.%, 43 wt.%, 44 wt.%, 45 wt.%, 46 wt.%, 47 wt.%, 48 wt.%, 49 wt.%, or 50 wt.% or any value therebetween. In some embodiments, the polyethyleneimine intermediate is present in the dry polymer or interpenetrating polymer network in an amount of from about 3 wt.% to about 30 wt.%.

[0584] In some embodiments, at least 20% of the nitrogen atoms in the polyethyleneimine intermediate are quaternized. In some embodiments, at least 30% of the nitrogen atoms in the polyethyleneimine intermediate are quaternized.

[0585] The molecular weight of the polyethyleneimine intermediate can be from about 300 Daltons to about 270,000 Daltons. This includes about 300 Daltons; 400 Daltons; 500 Daltons; 600 Daltons; 700 Daltons; 800 Daltons; 900 Daltons; 1000 Daltons; 2500 Daltons; 5000 Daltons; 10,000 Daltons; 25,000 Daltons; 50,000 Daltons; 75,000 Daltons; 100,000 Daltons; 125,000 Daltons; 150,000 Daltons; 175,000 Daltons; 200,000 Daltons; 225,000 Daltons; 250,000 Daltons; or 270,000 Daltons or any value therebetween. In some embodiments, the molecular weight of the polyethyleneimine is from about 10,000 Daltons to about 200,000 Daltons or from about 25,000 Daltons to about 120,000 Daltons.

[0586] In some embodiments, the polyethyleneimine is branched. In some embodiments, the polyethyleneimine is hyperbranched.

[0587] In some embodiments, the ratio of primary amine:secondary amine:tertiary amine of the polyethyleneimine is from about 1:2:1 to about 1:1:1. In some embodiments, the ratio of primary amine:secondary amine:tertiary amine of the polyethyleneimine is about 1:1:0.7.

[0588] In some embodiments, the polyethyleneimine intermediate is selected from

[0589] or a copolymer of two or more thereof, wherein:

[0590] Each Y 3 is independently H or -O-Y 2 wherein each Y 3 cannot be H;

[0591] Each Y 2 is independently H or –C(O)-NHR 30 wherein each Y 2 cannot be -C(O)-NHR 30 ;

[0592] Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000;

[0593] Z is -(C2-C6 alkylene)-;

[0594] Each R 10 is independently selected from hydrogen; C1-C6 alkyl optionally substituted with a substituent selected from: -N(R 20)3. (C6-C 10 aryl), and optionally -OH-substituted -(C1-C6 alkoxy), -(C1-C6 alkoxy), optionally -(C1-C6 alkyl)-substituted -(C6-C 10 aryl), and carboxyl; and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and optionally C6-C 10 aryl substituted with: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl);

[0595] each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl), and optionally -OH-substituted -(C1-C6 alkoxy);

[0596] each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1 to 3 substituents independently selected from: halogen, –SiR a (OR b )(OR c ), and -(C6-C 10 aryl); and (2) C6-C 10 aryl optionally substituted with 1 to 3 substituents independently selected from: halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c ); where each R a is independently C1-C6 alkyl; and each R b and each R c are independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3; and

[0597] each X -Independently selected from the group consisting of: acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and their organically substituted derivatives;

[0598] Provided that:

[0599] When R 10 is a C1-C6 alkyl optionally substituted with substituents selected from the following, then the polyethyleneimine intermediate is selected from

[0600] -(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl.

[0601] In some embodiments, the polyethyleneimine intermediate is selected from:

[0602]

[0603] where each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000.

[0604] In some embodiments, the second adduct has the formula (I):

[0605]

[0606] wherein:

[0607] each A is independently selected from

[0608] or a copolymer of any two or more thereof; and the attachment of each A forms a urethane bond;

[0609] each Y 3 is independently H or -O-Y 2 where each Y 3 cannot be H;

[0610] each Y 2 is independently H or –C(O)-NHR 30 where each Y 2 cannot be -C(O)-NHR 30 ;

[0611] Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000;

[0612] Z is -(C2-C6 alkylene)-;

[0613] Each R 10 is independently selected from hydrogen; C1-C6 alkyl optionally substituted with a substituent selected from: -N(R 20 )3, (C6-C 10 aryl), and -(C1-C6 alkoxy), -(C1-C6 alkoxy) optionally substituted with -OH, -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl; and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted with: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl);

[0614] Each R 21 is independently selected from C1-C6 alkyl optionally substituted with a substituent selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with -OH;

[0615] Each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1 to 3 substituents independently selected from: halogen, –SiR a (OR b )(OR c ), and -(C6-C 10 aryl); (2) C6-C 10 aryl optionally substituted with 1 to 3 substituents independently selected from: halogen, -(C1-C6 alkyl), and –SiR a (OR b )(OR c ); and (3) wherein each R aindependently is -(C1-C6 alkyl); and each R b and each R c independently is selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3;

[0616] each R 40 independently is -(C1-C 10 alkylene)- optionally substituted with phenyl or a 3- to 8-membered cycloalkyl ring; and

[0617] each X - independently is selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion, and borate ion, and their organically substituted derivatives;

[0618] provided that:

[0619] when R 10 is C1-C6 alkyl optionally substituted with a substituent selected from the following, then each A independently is selected from -(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl.

[0620] In some embodiments, the second adduct has the formula (II):

[0621]

[0622] wherein:

[0623] each A independently is selected from

[0624] or a copolymer of any two or more thereof; and the attachment of each A forms a urethane bond;

[0625] each Y 3 independently is H or -O-Y 2 where each Y 3 cannot be H;

[0626] each Y 2 independently is H or –C(O)-NHR 30 where each Y 2 cannot be -C(O)-NHR 30 ;

[0627] Each n is independently an integer selected from 1 to 3000, preferably an integer independently selected from 10 to 1000;

[0628] Z is -(C2-C6 alkylene)-;

[0629] Each R 10 is independently selected from hydrogen; C1-C6 alkyl optionally substituted with substituents selected from: -N(R 20 )3, (C6-C 10 aryl), and -(C1-C6 alkoxy), -(C1-C6 alkoxy) optionally substituted with -OH, -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl; and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tert-substituted N; and C6-C 10 aryl optionally substituted with: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl);

[0630] Each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with -OH;

[0631] Each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1 to 3 substituents independently selected from: halogen, –SiR a (OR b )(OR c ) and -(C6-C 10 aryl); (2) C6-C 10 aryl optionally substituted with 1 to 3 substituents independently selected from: halogen, -(C1-C6 alkyl), and –SiR a (OR b )(OR c ); and (3) where each R aindependently is -(C1-C6 alkyl); and each R b and each R c independently is selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3;

[0632] each R 40 independently is -(C1-C 10 alkylene)- optionally substituted by phenyl or a 3- to 8-membered cycloalkyl ring; and

[0633] each X - independently is selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and organically substituted derivatives thereof;

[0634] provided that:

[0635] when R 10 is C1-C6 alkyl optionally substituted by a substituent selected from the following, then each A independently is selected from -(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted by -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted by -(C1-C6 alkyl), and carboxyl.

[0636] In some embodiments, the second adduct is present in the dry polymer or interpenetrating polymer network in an amount of about 1 wt.% to about 30 wt.%. This includes about 1 wt.%, 2 wt.%, 3 wt.%, 4 wt.%, 5 wt.%, 6 wt.%, 7 wt.%, 8 wt.%, 9 wt.%, 10 wt.%, 11 wt.%, 12 wt.%, 13 wt.%, 14 wt.%, 15 wt.%, 16 wt.%, 17 wt.%, 18 wt.%, 19 wt.%, 20 wt.%, 21 wt.%, 22 wt.%, 23 wt.%, 24 wt.%, 25 wt.%, 26 wt.%, 27 wt.%, 28 wt.%, 29 wt.% or 30 wt.% or any value therebetween. In some embodiments, the second adduct is present in the dry polymer or interpenetrating polymer network in an amount of about 3 wt.% to about 15 wt.%.

[0637] The reagent for the random polymerization / crosslinking product may further comprise (i) a first polyfunctional crosslinking agent or a fourth polyfunctional crosslinking agent and (ii) a third adduct of a quaternary ammonium salt wherein

[0638] R1a 、R 2a and R 3a are each independently methyl or ethyl;

[0639] A 1 is a linking group selected from the group consisting of: -(C3-C 20 alkylene)-, -(C3-C 20 heteroalkylene)-, -(C6-C 10 arylene)-(C3-C 20 alkylene), -(CR m1 R n1 ) x42 -W 42 -(CR p1 R q1 ) y42 - and -(CR m1 R n1 ) x43 -W 43 -(CR p1 R q1 ) y43 -, where -(C3-C 20 heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; and -(C3-C 20 alkylene)- and -(C3-C 20 heteroalkylene)- are optionally substituted with 1 to 6 substituents independently selected from: -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl);

[0640] Each R m1 、R n1 、R p1 and R q1 is independently selected from H and C1-C4 alkyl;

[0641] W 42 is selected from -C(O)-; -C(O)O-; -OC(O)-; -C(O)NH-; and -NHC(O)-;

[0642] W 43 is selected from 5- to 6-membered cycloalkyl, C6-C 10Aryl, 5- to 6-membered heteroalkyl, and 5- to 6-membered heteroaryl, wherein the heteroalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si; and the heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si;

[0643] x42 is an integer from 1 to 19, and y42 is an integer from 1 to 19, where 3 ≤ (x42 + y42) ≤ 20;

[0644] x43 is an integer from 1 to 20, and y43 is an integer from 0 to 19, where 3 ≤ (x43 + y43) ≤ 20;

[0645] Y 1 Selected from the group consisting of: -OH, -NHR 4a 、-SH, -CO2H, -C(O)NHR 4a 、-C(S)NHR 4a 、

[0646]

[0647] Each R 4a Independently selected from the group consisting of: H, (C-(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl), where -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si; and

[0648] X - Independently is an acetate ion, a halide ion, a sulfate ion, a sulfonate ion, a phosphate ion, a phosphonate ion, a carbonate ion, a silicate ion, a hexafluorophosphate ion, a hexafluoroantimonate ion, a trifluoromethanesulfonate ion, a borate ion, or an organically substituted derivative of any of the foregoing.

[0649] The fourth polyfunctional crosslinking agent may be present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1 wt.% to about 15 wt.%. This includes 0.1 wt.%, 0.25 wt.%, 0.5 wt.%, 0.75 wt.%, 1 wt.%, 1.5 wt.%, 2 wt.%, 2.5 wt.%, 3 wt.%, 3.5 wt.%, 4 wt.%, 4.5 wt.%, 5 wt.%, 5.5 wt.%, 6 wt.%, 6.5 wt.%, 7 wt.%, 7.5 wt.%, 8 wt.%, 8.5 wt.%, 9 wt.%, 9.5 wt.%, 10 wt.%, 11 wt.%, 12 wt.%, 13 wt.%, 14 wt.% or 15 wt.% or any value therebetween. In some embodiments, the fourth polyfunctional crosslinking agent is present in the dry polymer or interpenetrating polymer network in an amount of from about 2 wt.% to about 8 wt.%.

[0650] In some embodiments, the fourth polyfunctional crosslinking agent may be different from the first polyfunctional crosslinking agent, and different from the second polyfunctional crosslinking agent if present, and different from the third polyfunctional crosslinking agent if present.

[0651] In some embodiments, the fourth polyfunctional crosslinking agent is a fourth polyisocyanate. In some embodiments, the fourth polyisocyanate is prepared from a diisocyanate selected from the group consisting of: hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), m-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI). In some embodiments, the fourth polyisocyanate is selected from the group consisting of: N-3300, N-100, Z4470SN, T series polyisocyanates and M series polyisocyanates.

[0652] In some embodiments, the second quaternary ammonium salt is (C2DMDEG-Br).

[0653] The secondary ammonium salt can be present in the dry polymer or interpenetrating polymer network in an amount of from about 1 wt.% to about 15 wt.%. This includes about 1 wt.%, 2 wt.%, 3 wt.%, 4 wt.%, 5 wt.%, 6 wt.%, 7 wt.%, 8 wt.%, 9 wt.%, 10 wt.%, 11 wt.%, 12 wt.%, 13 wt.%, 14 wt.%, or 15 wt.% or any value therebetween. In some embodiments, the secondary ammonium salt is present in the dry polymer or interpenetrating polymer network in an amount of from about 3 wt.% to about 10 wt.%.

[0654] In some embodiments, the average isocyanate functionality of the third adduct is from 2 to 3. In some embodiments, the average isocyanate functionality of the third adduct is from 2.05 to about 2.3.

[0655] The third adduct can be present in the dry polymer or interpenetrating polymer network in an amount of from about 2 wt.% to about 30 wt.%. This includes about 2 wt.%, 3 wt.%, 4 wt.%, 5 wt.%, 6 wt.%, 7 wt.%, 8 wt.%, 9 wt.%, 10 wt.%, 11 wt.%, 12 wt.%, 13 wt.%, 14 wt.%, 15 wt.%, 16 wt.%, 17 wt.%, 18 wt.%, 19 wt.%, 20 wt.%, 21 wt.%, 22 wt.%, 23 wt.%, 24 wt.%, 25 wt.%, 26 wt.%, 27 wt.%, 28 wt.%, 29 wt.%, or 30 wt.% or any value therebetween. In some embodiments, the secondary ammonium salt is present in the dry polymer or interpenetrating polymer network in an amount of from about 3 wt.% to about 20 wt.%.

[0656] The reagent for the random polymerization / crosslinked product can further comprise a chain extender selected from the group consisting of HO-(C n H 2n )-OH and HO-(C n H 2n-2 )-OH or a combination thereof, where n is an integer from 2 to 8. In some embodiments, the chain extender is propylene glycol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexanedimethanol, or a combination of two or more thereof. The chain extender can be present in the dry polymer or interpenetrating polymer network in an amount of from about 0.5 wt.% to about 10 wt.%. This includes about 0.5 wt.%, 1 wt.%, 2 wt.%, 3 wt.%, 4 wt.%, 5 wt.%, 6 wt.%, 7 wt.%, 8 wt.%, 9 wt.%, or 10 wt.% or any value therebetween. In some embodiments, the chain extender can be present in the dry polymer or interpenetrating polymer network in an amount of from about 1 wt.% to about 5 wt.%.

[0657] On the other hand, the present disclosure provides a polymer or an interpenetrating polymer network comprising a random polymerization / crosslinking product of reagents, the reagents comprising, consisting essentially of, or consisting of: (i) a first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt; (ii) optionally a polyol; (iii) a polyethyleneimine intermediate or a second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinking agent; (iv) optionally a third polyfunctional crosslinking agent; (v) optionally a third adduct of (a) a first polyfunctional crosslinking agent or a fourth polyfunctional crosslinking agent and (b) a second quaternary ammonium salt; (vi) optionally a chain extender; and (vii) a water-soluble polymer.

[0658] On the other hand, the present disclosure provides a polymer or an interpenetrating polymer network comprising a random polymerization / crosslinking product of reagents, the reagents comprising, consisting essentially of, or consisting of: (i) a first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt; (ii) optionally a polyol; (iii) a polyethyleneimine intermediate or a second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinking agent; (iv) optionally a third polyfunctional crosslinking agent; (v) optionally a third adduct of (a) a first polyfunctional crosslinking agent or a fourth polyfunctional crosslinking agent and (b) a second quaternary ammonium salt; and (vi) optionally a chain extender.

[0659] In some embodiments, a first quaternary ammonium salt reacts with a first polyisocyanate to form a first adduct, wherein the first adduct retains unreacted isocyanate functional groups from the first polyisocyanate. In some embodiments, about 10% to about 40%, preferably about 25% to about 33% of the isocyanate functional groups on the first polyisocyanate are converted to, for example, urethane or urea by reaction with the first quaternary ammonium salt. The unreacted isocyanate functional groups then react with one or more of the following: a polyol (if present), a chain extender (if present), a polyethyleneimine intermediate or a second adduct, water, and a water-soluble polymer (if reactive). Similarly, in some embodiments, a second quaternary ammonium salt reacts with a first polyisocyanate or a fourth polyisocyanate to form a third adduct, wherein the third adduct retains unreacted isocyanate functional groups from the first polyisocyanate or the fourth polyisocyanate. In some embodiments, about 10% to about 40%, preferably about 25% to 33% of the isocyanate functional groups on the first polyisocyanate or the fourth polyisocyanate are converted to, for example, urethane or urea by reaction with the second quaternary ammonium salt. If present, the third polyfunctional crosslinker and / or the third adduct can also react with one or more of the following: a polyol (if present), a chain extender (if present), a polyethyleneimine intermediate or a second adduct, water, and a water-soluble polymer (if reactive). The first adduct and the third adduct are pre-formed prior to interacting with a polyol (if present), a chain extender (if present), a polyethyleneimine intermediate or a second adduct, and a water-soluble polymer (if reactive).

[0660] On the other hand, a polymer or an interpenetrating polymer network is prepared by:

[0661] (a) Reacting a first polyfunctional crosslinker with a first quaternary ammonium salt to form a first adduct;

[0662] (b) Optionally reacting a polyethyleneimine intermediate with a second polyfunctional crosslinker to form a second adduct;

[0663] (c) Optionally reacting the first polyfunctional crosslinker or a fourth polyfunctional crosslinker with a second quaternary ammonium salt to form a third adduct;

[0664] (d) Combining (i) the first adduct, (ii) the polyethyleneimine intermediate or the second adduct, and (iii) when present, the third adduct with an optional polyol and an optional third polyfunctional crosslinker to form an oil phase;

[0665] (e) Dissolving a water-soluble polymer in water to form an aqueous phase;

[0666] (f) Combine the oil phase and the water phase to form an oil-in-water emulsion; and

[0667] (g) Apply the emulsion to a surface and allow the emulsion to dry and cure on the surface to form the polymer or interpenetrating polymer network on the surface.

[0668] In some embodiments, a blocking agent is added to the oil phase after step (d) but before step (f).

[0669] In some embodiments, step (d) further comprises combining (i) the first adduct, (ii) the polyethyleneimine intermediate or the second adduct, and (iii) when present, the third adduct with optionally the polyol and optionally the second polyfunctional crosslinking agent in an organic solvent or diluent to form the oil phase.

[0670] In some embodiments, step (d) further comprises adding a chain extender to the oil phase. In some embodiments, step (e) further comprises adding a chain extender to the water phase.

[0671] In some embodiments, step (e) further comprises adding a surfactant to the water phase. In some embodiments, step (e) further comprises adding an antifoaming agent or defoaming agent to the water phase. In some embodiments, step (e) further comprises adding either a surfactant or an antifoaming agent or defoaming agent to the water phase.

[0672] In some embodiments, step (f) further comprises performing a direct emulsification process whereby the emulsion is formed by intense shearing and mixing. In some embodiments, step (f) further comprises performing a direct emulsification process whereby the emulsion is formed by sonication.

[0673] In some embodiments, step (f) further comprises performing a phase inversion emulsification process whereby a water-in-oil emulsion is first prepared and subsequently phase inversion is carried out to form the oil-in-water emulsion. Phase inversion can be carried out by, for example, changing the phase ratio, temperature, surfactant, solvent or any combination of two or more thereof.

[0674] In some embodiments, a multiphase water-in-oil-in-water emulsion is formed before conversion to the oil-in-water emulsion in step (f).

[0675] In some embodiments, in step (f), the oil phase and the water phase are combined to form a combination of an oil-in-water emulsion and a multiphase water-in-oil-in-water emulsion.

[0676] On the other hand, the reagents for preparing the polymers or interpenetrating polymer networks described herein are included in an antimicrobial composition.

[0677] Accordingly, on the other hand, the present disclosure provides an antimicrobial composition comprising an oil-in-water emulsion, wherein the oil-in-water emulsion comprises

[0678] (i) an oil phase comprising

[0679] a first adduct of a first polyfunctional crosslinker and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group for reacting with the first polyfunctional crosslinker;

[0680] optionally a polyol;

[0681] a polyethyleneimine intermediate or a second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinker; and

[0682] optionally a third polyfunctional crosslinker; and

[0683] (ii) an aqueous phase comprising a water-soluble polymer.

[0684] This composition can be applied to a surface and allowed to dry and cure, thereby forming the polymers or interpenetrating polymer networks of the present technology.

[0685] The reactive linking group of the first quaternary ammonium salt can be selected from the group consisting of: -OH, -NHR 4 , -SH, -CO2H, -C(O)NHR 4 , -C(S)NHR 4 , wherein each R 4 is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl), wherein -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S and Si.

[0686] Based on the dry weight of the oil phase, the first quaternary ammonium salt as described herein and incorporated into the first adduct can be present in the oil phase in an amount of from about 1 wt% to about 50 wt%. As used herein, unless otherwise specified, "dry weight of the oil phase" refers to the weight of the oil phase in the absence of any organic solvents and any water. This includes about 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, 40%, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49% or 50% or any value therebetween. In some embodiments, based on the dry weight of the oil phase, the first quaternary ammonium salt incorporated into the first adduct is present in the oil phase in an amount of from about 1 wt% to about 25 wt% or from about 5 wt% to about 25 wt%.

[0687] Based on the dry weight of the oil phase, the first polyfunctional crosslinking agent (e.g., the first polyisocyanate) as described herein and incorporated into the first adduct can be present in the oil phase in an amount of from about 2 wt% to about 25 wt%. This includes about 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24% or 25% or any value therebetween. In some embodiments, based on the dry weight of the oil phase, the first polyfunctional crosslinking agent (e.g., the first polyisocyanate) incorporated into the first adduct is present in the oil phase in an amount of from about 5 wt% to about 20 wt%.

[0688] Based on the dry weight of the oil phase, the first adduct as described herein can be present in the oil phase in an amount of from about 5 wt% to about 70 wt%. This includes about 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, 40%, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, 50%, 51%, 52%, 53%, 54%, 55%, 56%, 57%, 58%, 59%, 60%, 61%, 62%, 63%, 64%, 65%, 66%, 67%, 68%, 69% or 70% or any value therebetween. In some embodiments, based on the dry weight of the oil phase, the first adduct is present in the oil phase in an amount of from about 10 wt% to about 50 wt%, from about 15 wt% to about 65 wt%, from about 15 wt% to about 60 wt%, from about 15 wt% to about 50 wt%, from about 20 wt% to about 70 wt%, from about 20 wt% to about 60 wt% or from about 20 wt% to about 50 wt%.

[0689] Based on the dry weight of the oil phase, the polyethyleneimine intermediate as described herein can be present in the oil phase in an amount of from about 0.1 wt% to about 50 wt%. This includes 0.1%, 0.25%, 0.5%, 0.75%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%, 5.5%, 6%, 6.5%, 7%, 7.5%, 8%, 8.5%, 9%, 9.5%, 10%, 10.5%, 11%, 11.5%, 12%, 12.5%, 13%, 13.5%, 14%, 14.5%, 15%, 15.5%, 16%, 16.5%, 17%, 17.5%, 18%, 18.5%, 19%, 19.5%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, 40%, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49% or 50% or any value therebetween. In some embodiments, based on the dry weight of the oil phase, the polyethyleneimine intermediate is present in the oil phase in an amount of from about 3 wt% to about 30 wt%.

[0690] Based on the dry weight of the oil phase, the second polyfunctional crosslinking agent (e.g., the second polyisocyanate) incorporated into the second adduct as described herein can be present in the oil phase in an amount of from about 0.1 wt% to about 10 wt%. This includes about 0.1%, 0.25%, 0.5%, 0.75%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%, 5.5%, 6%, 6.5%, 7%, 7.5%, 8%, 8.5%, 9%, 9.5% or 10% or any value therebetween. In some embodiments, based on the dry weight of the oil phase, the second polyfunctional crosslinking agent (e.g., the second polyisocyanate) is present in the oil phase in an amount of from about 2 wt% to about 8 wt% or from about 3 wt% to about 6 wt%.

[0691] Based on the dry weight of the oil phase, the second adduct as described herein can be present in the oil phase in an amount of from about 1 wt% to about 30 wt%. This includes about 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29% or 30% or any value therebetween. In some embodiments, based on the dry weight of the oil phase, the second adduct is present in the oil phase in an amount of from about 3 wt% to about 15 wt%.

[0692] In some embodiments, the oil phase further comprises a third polyfunctional crosslinking agent as described herein. Based on the dry weight of the oil phase, the third polyfunctional crosslinking agent (e.g., the third polyisocyanate) can be present in the oil phase in an amount of from about 5 wt% to about 25 wt%. This includes about 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24% or 25% or any value therebetween. In some embodiments, based on the dry weight of the oil phase, the third polyfunctional crosslinking agent (e.g., the third polyisocyanate) is present in the oil phase in an amount of from about 5 wt% to about 20 wt%.

[0693] In some embodiments, the oil phase further comprises a third adduct as described herein. Based on the dry weight of the oil phase, the third adduct may be present in the oil phase in an amount of from about 2 wt% to about 30 wt%. This includes about 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29% or 30% or any value therebetween. In some embodiments, based on the dry weight of the oil phase, the third adduct is present in the oil phase in an amount of from about 3 wt% to about 20 wt%.

[0694] In some embodiments, based on the dry weight of the oil phase, the second quaternary ammonium salt as described herein and incorporated into the third adduct may be present in the oil phase in an amount of from about 1 wt% to about 15 wt%. This includes about 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14% or 15% or any value therebetween. In some embodiments, based on the dry weight of the oil phase, the second quaternary ammonium salt incorporated into the third adduct as described herein is present in the oil phase in an amount of from about 3 wt% to about 10 wt%.

[0695] Based on the dry weight of the oil phase, the fourth polyfunctional crosslinker (e.g., the fourth polyisocyanate) as described herein and incorporated into the third adduct may be present in the oil phase in an amount of from about 0.1 wt% to about 15 wt%. This includes about 0.1%, 0.25%, 0.5%, 0.75%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%, 4.5%, 6%, 6.5%, 7%, 7.5%, 8%, 8.5%, 9%, 9.5%, 10%, 11%, 12%, 13%, 14% or 15% or any value therebetween. In some embodiments, based on the dry weight of the oil phase, the fourth polyfunctional crosslinker (e.g., the fourth polyisocyanate) as described herein and incorporated into the third adduct is present in the oil phase in an amount of from about 2 wt% to about 8 wt%.

[0696] In some embodiments, the reactive isocyanate functional groups on the first adduct and / or the third adduct are protected with a blocking agent. The reaction with the blocking agent converts the reactive isocyanate functional groups into blocked isocyanates (i.e., the isocyanate groups are reversibly protected and will not immediately react with nucleophiles). This reduces the rate of reaction of the polyisocyanate with water in subsequent emulsification steps and / or crosslinking reactions with any polyols in the oil phase and / or water-soluble polymers (such as hydroxyethyl cellulose) in the aqueous phase. In some embodiments, the rheological properties, particle size, and reproducibility of the distribution of the resulting emulsion are significantly improved. In some embodiments, the coatability and process window of the coating process are also significantly improved. In some embodiments, the defect rate of the resulting surface coating is reduced, and the production rate of the coated product is also improved. In some embodiments, no blocking agent is used to provide a more rapidly curing coating.

[0697] In some embodiments, the blocking agent is selected from the group consisting of: oximes, phenols, malonic esters, alcohols, lactams, dicarbonyl compounds, isohydroxamic acid esters, bisulfite addition compounds, hydroxylamines, esters of p-hydroxybenzoic acid, and salicylic acid. In some embodiments, the blocking agent is selected from the group consisting of: acetone oxime, methyl ethyl ketone oxime, sodium bisulfite, diethyl malonate, and 3,5-dimethylpyrazole.

[0698] In some embodiments, the composition further comprises a deblocking agent. Deblocking agents include, but are not limited to, organotin, organobismuth, and tertiary amines. Non-limiting examples include triethanolamine; N,N,N'N'-tetrakis(2-hydroxyethyl)ethylenediamine; and K-KAT XK-651 (bismuth formate catalyst).

[0699] In some embodiments, the oil phase further comprises a chain extender selected from the group consisting of: HO-(C n H 2n )-OH and HO-(C n H 2n-2 )-OH or combinations thereof, where n is an integer from 2 to 8. In some embodiments, the chain extender is propylene glycol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexanedimethanol, or a combination of two or more thereof. Based on the dry weight of the oil phase, the chain extender may be present in the oil phase in an amount of up to about 10 wt%. This includes about 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or any value therebetween. In some embodiments, based on the dry weight of the oil phase, the chain extender is present in the oil phase in an amount of about 0.5 wt% to about 10 wt% or about 1 wt% to about 5 wt%.

[0700] In some embodiments, the oil phase further comprises an organic solvent or a diluent. In some embodiments, the organic solvent or diluent in the oil phase is water-miscible. In some embodiments, the organic solvent or diluent is acetone. In some embodiments, based on the weight of the oil phase, the organic solvent or diluent is present in the oil phase in an amount of about 5 wt% to about 35 wt%. This includes about 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, or 35% or any value therebetween. In some embodiments, based on the weight of the oil phase, the organic solvent or diluent is present in the oil phase in an amount of about 10 wt% to about 30 wt%.

[0701] Based on the dry weight of the oil phase, the polyol may be present in the oil phase in an amount of about 1 wt% to about 40 wt%. This includes about 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, or 40% or any value therebetween. In some embodiments, based on the dry weight of the oil phase, the polyol is present in the oil phase in an amount of about 5 wt% to about 25 wt%.

[0702] The weight percentage of the water-soluble polymer in the aqueous phase is calculated by the amount present in the oil phase that interacts with the oil phase itself and / or the oil phase components (e.g., the first adduct, the optional second polyfunctional crosslinking agent). The water-soluble polymer as described herein may be present in the aqueous phase in an amount of about 0.5 wt% to about 15 wt% based on the dry weight of the oil phase. This includes about 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, or 15% or any value therebetween. In some embodiments, the water-soluble polymer as described herein is present in the aqueous phase in an amount of about 3 wt% to about 12 wt% or about 5 wt% to about 10 wt% based on the dry weight of the oil phase.

[0703] The water-soluble polymer can be a reactive water-soluble polymer and crosslinked with one or more of the first adduct and the third polyfunctional crosslinking agent (if present). In some embodiments, the water-soluble polymer is a reactive water-soluble polymer and crosslinked with any combination of the first adduct, the third polyfunctional crosslinking agent (if present), the third adduct (if present), or two or more of them.

[0704] In some embodiments, the water-soluble polymer is a non-reactive water-soluble polymer and not covalently bonded to any components in the oil phase or the water phase (e.g., any combination of the first adduct, the third polyfunctional crosslinking agent (if present), the third adduct (if present), or two or more of them).

[0705] In some embodiments, the water phase further comprises a water-soluble low molecular weight chain extender or crosslinking agent. Including a water-soluble low molecular weight chain extender or crosslinking agent can increase the degree of crosslinking of the random polymerization product. Examples of water-soluble low molecular weight chain extenders or crosslinking agents include but are not limited to polyfunctional amines such as ethylenediamine, diethylenetriamine, and triethylenetetramine.

[0706] In some embodiments, the water phase further comprises a surfactant. In some embodiments, the surfactant is a non-ionic surfactant. In some embodiments, the average HLB (hydrophilic-lipophilic balance) value of the non-ionic surfactant is preferably from about 12 to about 15. Non-ionic surfactants include but are not limited to TRITON TM X-114 ((1,1,3,3-tetramethylbutyl)phenyl-polyethylene glycol), SILWET TM L-7604 (siloxane polyalkylene oxide copolymer), and combinations thereof.

[0707] The weight percentage of the surfactant in the water phase is calculated by the amount present in the oil phase that interacts with or adsorbs on the oil phase. Based on the dry weight of the oil phase, the surfactant can be present in the water phase in an amount of about 0.01 wt% to about 2 wt%. This includes about 0.05%, 0.075%, 0.1%, 0.25%, 0.5%, 0.75%, 1%, 1.25%, 1.5%, 1.75%, or 2% or any value therebetween. In some embodiments, based on the dry weight of the oil phase, the surfactant is present in the water phase in an amount of about 0.05 wt% to about 2 wt% or about 0.1 wt% to about 1 wt%.

[0708] In some embodiments, the water phase further comprises an antifoaming agent or defoaming agent. In some embodiments, the antifoaming agent is ST 2410 (star-polymer-based antifoaming agent).

[0709] Polyethyleneimine intermediates can be used as antimicrobial compounds. In some embodiments, quaternization occurs not on the polyethyleneimine backbone but on side-chain substitutions. Thus, on the other hand, there is provided an antimicrobial compound selected from the following:

[0710]

[0711] or a copolymer of two or more thereof, wherein:

[0712] each Y 3 is independently H or -O-Y 2 where each Y 3 cannot be H;

[0713] each Y 2 is independently H or -C(O)-NHR 30 where each Y 2 cannot be -C(O)-NHR 30 ;

[0714] each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000;

[0715] Z is -(C2-C6 alkylene)-;

[0716] each R 10 is a C1-C6 alkyl substituted by -N + (R 20 )3X - and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tert-substituted N; and C6-C 10 aryl optionally substituted by: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl);

[0717] each R 21 is independently selected from C1-C6 alkyl optionally substituted by substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted by -OH;

[0718] Each R 30 is independently selected from (1) C6-C optionally substituted with 1-3 substituents independently selected from the following 20 alkyl: halogen, –SiR a (OR b )(OR c ) and -(C6-C 10 aryl); and (2) C6-C optionally substituted with 1-3 substituents independently selected from the following 10 aryl: halogen, -(C1-C6 alkyl) and -SiR a (OR b )(OR c ); wherein each R a is independently C1-C6 alkyl; and each R b and each R c are independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3; and

[0719] Each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and organically substituted derivatives thereof.

[0720] In some embodiments, each Y 2 is H. In some embodiments, the compound is

[0721]

[0722] wherein each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000.

[0723] A second adduct (which is a random polymerization product of a polyethyleneimine intermediate and a (polyfunctional) crosslinker disclosed herein) can be used as an antimicrobial compound. Thus, on the other hand, there is provided herein a random polymerization product of a polyethyleneimine intermediate and a crosslinker, wherein the polyethyleneimine intermediate is selected from:

[0724]

[0725] or a copolymer of two or more thereof, wherein:

[0726] Each Y 3 is independently H or -O-Y 2 , wherein each Y 3Cannot be H;

[0727] Each Y 2 Is independently H or -C(O)-NHR 30 Wherein each Y 2 Cannot be -C(O)-NHR 30 ;

[0728] Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000;

[0729] Z is -(C2-C6 alkylene)-;

[0730] Each R 10 Is -N + (R 20 )3X - Substituted C1-C6 alkyl, and each R 20 Is independently selected from the group consisting of: C1-C 18 Alkyl; C1-C 18 Heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tert-substituted N; and optionally substituted C6-C 10 Aryl: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl);

[0731] Each R 21 Is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 Aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 Aryl), and -(C1-C6 alkoxy) optionally substituted with -OH;

[0732] Each R 30 Is independently selected from (1) C6-C 20 Alkyl optionally substituted with 1 to 3 substituents independently selected from: halogen, –SiR a (OR b )(OR c ) and -(C6-C 10 Aryl); and (2) C6-C 10 Aryl optionally substituted with 1 to 3 substituents independently selected from: halogen, -(C1-C6 alkyl), and -SiR a (OR b )(ORc ); wherein each R a is independently a C1-C6 alkyl group; and each R b and each R c is independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3; and

[0733] each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and their organically substituted derivatives.

[0734] In some embodiments, the crosslinking agent is a polyisocyanate. In some embodiments, the polyisocyanate is prepared from diisocyanates independently selected from the group consisting of: hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), m-tetramethylxylene diisocyanate (TMXDI) and trimethylhexamethylene diisocyanate (TMDI). In some embodiments, the polyisocyanate is independently selected from the group consisting of: N-3300, N-100, Z4470SN, T series polyisocyanates and M series polyisocyanates.

[0735] In some embodiments, the random polymerization product has the formula (I):

[0736]

[0737] Wherein:

[0738] each A is independently selected from

[0739] or a copolymer of any two or more thereof; and the attachment of each A forms a urethane bond;

[0740] each Y 3 is independently H or -O-Y 2 wherein each Y 3 cannot be H;

[0741] each Y 2 is independently H or –C(O)-NHR30 , wherein each Y 2 is not -C(O)-NHR 30 ;

[0742] Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000;

[0743] Z is -(C2-C6 alkylene)-;

[0744] Each R 10 is -N + (R 20 )3X - substituted C1-C6 alkyl, and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si and tert-substituted N; and optionally substituted C6-C 10 aryl: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2 or -OC(O)-(C1-C6 alkyl);

[0745] Each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH;

[0746] Each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1 to 3 substituents independently selected from: halogen, –SiR a (OR b )(OR c ) and -(C6-C 10 aryl); (2) C6-C 10 aryl optionally substituted with 1 to 3 substituents independently selected from: halogen, -(C1-C6 alkyl) and –SiR a (OR b )(OR c ); and (3) wherein each R a is independently -(C1-C6 alkyl); and each Rb and each R c is independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3;

[0747] each R 40 is independently -(C1-C 10 alkylene)- optionally substituted with phenyl or a 3- to 8-membered cycloalkyl ring; and

[0748] each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion, and borate ion, and their organically substituted derivatives.

[0749] In some embodiments, the random polymerization product has the formula (II):

[0750]

[0751] wherein:

[0752] each A is independently selected from

[0753] or a copolymer of any two or more thereof; and the attachment of each A forms a urethane bond;

[0754] each Y 3 is independently H or -O-Y 2 , where each Y 3 cannot be H;

[0755] each Y 2 is independently H or –C(O)-NHR 30 where each Y 2 cannot be -C(O)-NHR 30 ;

[0756] each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000;

[0757] Z is -(C2-C6 alkylene)-;

[0758] each R 10 is C1-C6 alkyl substituted with -N + (R 20 )3X - and each R 20 is independently selected from the group consisting of C1-C 18alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si and tert-substituted N 18 heteroalkyl; and optionally C6-C substituted with the following 10 aryl: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2 or -OC(O)-(C1-C6 alkyl);

[0759] each R 21 independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH;

[0760] each R 30 independently selected from (1) C6-C optionally substituted with 1 to 3 substituents independently selected from the following 20 alkyl: halogen, –SiR a (OR b )(OR c ) and -(C6-C 10 aryl); (2) C6-C optionally substituted with 1 to 3 substituents independently selected from the following 10 aryl: halogen, -(C1-C6 alkyl) and –SiR a (OR b )(OR c ); and (3) wherein each R a is independently -(C1-C6 alkyl); and each R b and each R c is independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3;

[0761] each R 40 is independently -(C1-C optionally substituted with phenyl or a 3- to 8-membered cycloalkyl ring 10 alkylene)-; and

[0762] each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and organically substituted derivatives thereof.

[0763] It should be understood that the polymers described herein and the general methods for preparing such polymers provide great versatility to adjust and fine-tune physical and chemical properties as well as their antimicrobial properties for a wide variety of different surfaces, substrates, and applications. Examples of variables that can be used for such fine-tuning include, but are not limited to, a first quaternary ammonium salt, an optional polyol, an optional chain extender, a water-soluble polymer, a first polyfunctional crosslinker (e.g., a first polyisocyanate), a polyethyleneimine intermediate or a second adduct (and its second polyfunctional crosslinker, e.g., a second polyisocyanate), an optional third polyfunctional crosslinker (e.g., a third polyisocyanate), an optional second quaternary ammonium salt, an optional fourth polyfunctional crosslinker (e.g., a fourth polyisocyanate), and the structure and amount thereof, as well as the degree of crosslinking. It should also be understood that polyfunctional crosslinkers other than polyisocyanates can be used, such as, but not limited to, polyfunctional epoxides, imines, carbodiimides, and aldehydes.

[0764] On the other hand, the present disclosure provides an antimicrobial coating, coating fluid, or spraying fluid that comprises, consists essentially of, or consists of the antimicrobial composition described herein. In some embodiments, the coating fluid or the spraying fluid is water-soluble or water-dispersible.

[0765] On the other hand, the present disclosure provides a device, equipment, apparatus, or fitting that comprises the antimicrobial coating, coating fluid, or spraying fluid described herein. Non-limiting examples of the device, equipment, apparatus, or fitting include filters, air purifiers, face masks, or other personal protective devices (PPDs), respirators, etc. Other non-limiting examples include keyboards, keypads, styli, mice, remote controllers, touchscreens, telephones, and displays, or any device that integrates any of the foregoing components.

[0766] On the other hand, the present disclosure provides a personal care aid that comprises the coating, coating fluid, or spraying fluid described herein. Non-limiting examples of the personal care aid include facial tissues, hand sanitizers, and cleaning pads.

[0767] Method of Use

[0768] On the other hand, the present disclosure provides a method for disinfecting a surface, the method comprising, consisting essentially of, or consisting of applying the composition disclosed herein to the surface.

[0769] On the other hand, the present disclosure provides a method for reducing (e.g., minimizing) antimicrobial growth on a surface, the method comprising, consisting essentially of, or consisting of: applying a composition disclosed herein to the surface. In some embodiments, the method includes forming a coating solution containing a composition according to any one of the embodiments shown herein. The method further includes directing the coating solution onto the surface by an applicator (e.g., a sprayer), and providing a coating on the surface by applying the coating solution to the surface.

[0770] On the other hand, the present disclosure provides a method for preventing antimicrobial growth on a surface, the method comprising, consisting essentially of, or consisting of: applying a composition disclosed herein to the surface.

[0771] In some embodiments of the methods described above, the applying step comprises, consists essentially of, or consists of: spraying or brushing the surface with the composition. In some embodiments of the methods described above, the applying step comprises, consists essentially of, or consists of: dipping the surface into a coating solution containing a composition according to any one of the embodiments shown herein. In some embodiments of the methods described above, the applying step comprises, consists essentially of, or consists of: applying the composition to the surface by an electrostatic process.

[0772] The description of embodiments of the present disclosure is not intended to be exhaustive or to limit the present disclosure to the precise forms disclosed. Although specific embodiments and examples of the present disclosure are described herein for illustrative purposes, various equivalent modifications will be recognized by those skilled in the relevant art as being within the scope of the present disclosure. For example, while method steps or functions are presented in a given order, alternative embodiments may perform functions in a different order or may perform functions substantially simultaneously. The teachings of the present disclosure provided herein may be suitably applied to other processes or methods. The various embodiments described herein may be combined to provide additional embodiments. If necessary, aspects of the present disclosure may be modified to utilize the compositions, functions, and concepts of the above references and applications to provide yet another embodiment of the present disclosure. Additionally, due to considerations of biological functional equivalence, some changes may be made to the protein structure without affecting the type or amount of biological action. These and other changes may be made to the present disclosure in accordance with the detailed description. All such modifications are intended to be included within the scope of the appended claims.

[0773] Specific elements of any of the foregoing embodiments may be combined with or replace elements in other embodiments. Additionally, although advantages associated with certain embodiments of the present disclosure have been described in the context of these embodiments, other embodiments may also exhibit these advantages and not all embodiments need to exhibit these advantages to fall within the scope of the present disclosure.

[0774] The techniques described herein are further illustrated by the following examples, which should in no way be construed as further limitations. Although methods and materials similar or equivalent to those described herein may be used to practice or test the present disclosure, suitable methods and materials are described below.

[0775] Examples

[0776] The present technology is now described generally, and will be more readily understood by reference to the following examples. These examples are included only to illustrate certain aspects and embodiments of the present technology and are not intended to limit the present technology.

[0777] Evaluation of the antiviral activity of the polymer and / or its coating

[0778] The evaluation of the antiviral activity of the polymer coating of the present technology is carried out as follows. All samples and all accessories in the evaluation are first sterilized by autoclaving, alcohol cleaning, or UV laminar flow chamber irradiation.

[0779] First, adenovirus (108 PFU / mL, plaque forming units, MOI = 100 multiplicity of infection) is diluted in phosphate buffered saline (PBS) to 2×10 7 PFU / ml. Then, 0.1 mL of the diluted virus solution is deposited on the sterilized sample.

[0780] The antiviral activity is determined by two different methods: (i) the human cell (HuH7) method; and (ii) the quantitative reverse transcription polymerase chain reaction (RT-qPCR) method.

[0781] (i) The human cell (HuH7) method

[0782] Huh7 is a human hepatocyte cell line that can be grown in the laboratory for research purposes. According to the website huh7.com, it is "a well-differentiated hepatocyte-derived cancer cell line originally collected from the liver tumor of a 57-year-old Japanese male in 1982".

[0783] To evaluate the antiviral activity, 0.1 mL of the virus (adenovirus) in Dulbecco's Modified Eagle Medium (DMEM) + 10% fetal bovine serum (FBS) medium was dropped onto the coating and also onto the control substrate, and it was left on the coating for 30 minutes. The virus / media mixture was transferred to a Petri dish containing HuH7 cells (human hepatocytes) in the medium. The residual virus on the coating was rinsed twice with 0.1 mL of the medium, and the liquid was combined with the virus fluid in the Petri dish. The Petri dish was transferred to a CO2 incubator and incubated at 37 °C and at a relative humidity of approximately 95% and a CO2 concentration of approximately 5% for 48 hours to amplify the signal.

[0784] After incubation, visible light and fluorescence micrographs were taken of the virus / cell samples to determine the populations of virus and live / dead cells. For the positive control, 0.1 mL of the virus in the medium was directly transferred to a Petri dish containing HuH7 cells in the medium.

[0785] (ii) RT-qPCR method

[0786] RT-qPCR is used for a variety of applications, including pathogen detection, gene expression analysis, RNAi validation, microarray validation, genetic testing, and disease research.

[0787] Sample preparation

[0788] The medium (DMEM, high glucose, pyruvate; Thermo Fisher Scientific, catalog number: 11995040) was taken out of the refrigerator and conditioned in a 37 °C water bath for 30 minutes.

[0789] Preparation of virus fluid: The typical virus count in stock is 5 λ (5×10 8 ) per tube. 1 mL of DMEM medium was added to the virus tube, and the tube was mixed evenly with a vortex mixer for 5 - 10 seconds to make a virus fluid with a concentration of 5×10 8 / mL. The virus fluid was further diluted to 5×10 7 / mL with DMEM medium for antiviral testing.

[0790] RT-qPCR procedure for the coating: The coated film was immersed in 99% alcohol for 1 second. Excess alcohol was removed from the surface. Then the film was air-dried in a new Petri dish for 15 - 20 minutes. Then 100 μL of the diluted virus fluid (5×10 6Add (x mL) dropwise onto the dry film. Cover the Petri dish and allow the virus to contact the film for the desired contact period. In some experiments, the contact time was reduced to as short as 30 seconds. Transfer the virus fluid from the film to an Eppendorf tube. Then rinse the film twice with 50 μL of 1X PBD and combine the rinse fluids into the Eppendorf tube. The total test fluid volume is 200 μL and is ready for DNA extraction.

[0791] RT-qPCR procedure for aqueous solution: Add 100 μL of the test sample to 100 μL of the diluted virus fluid (5×10 7 / mL) in an Eppendorf tube and mix the mixture (5×10 6 virus count) on an oscillator for 30 minutes. Extract DNA using the Novogene DNA kit according to the specified extraction procedure.

[0792] RT-qPCR test: Each sample is tested in quadruplicate. Thoroughly mix the components listed in Table 1 in an Eppendorf tube.

[0793] Table 1 - Preparation of the premix for q-RT-PCR test

[0794]

[0795]

[0796] EGFP primer sequence:

[0797]

[0798] Add 10 μL of the premix to each well of the test plate, take three samples for each coating, and perform each sample in quadruplicate. Thus, a total of 12 tests are performed for each coating.

[0799] Centrifuge the plate to ensure that all the premix fluid flows to the bottom of the well. Then insert the plate into an Applied Biosystems QuantStudio 3 (Thermo Fisher Scientific) to determine the cycle threshold (CT) number for calculating the antiviral efficiency. Quantitatively calculate the antiviral efficiency based on the CT value.

[0800] Test

[0801] Qualitative cell viability test of the coating: Place the coating in a Petri dish, and drop 100 μL of DMEM medium onto the coating. Then cover the Petri dish for 30 minutes. Then transfer the medium on the film to a cell plate, which contains 8×10 4 cells in 500 μL of medium in each well. Rinse the film twice with 50 μL of DMEM medium, and combine the rinsing fluid with the previous test fluid in the same position in the plate. Add a total of 200 μL of the test fluid to 500 μL of cells / medium. Incubate the cell plate in a 37 °C / 95% RH CO₂ incubator for 48 - 96 hours, and then observe cell growth and morphology under a visible microscope. Dead cells float or are suspended in the medium, while live cells remain attached to the bottom of the plate. This test is used to evaluate the contact cytotoxicity of the polymer film. In the case where this test indicates a certain degree of cytotoxicity, no actual mechanism of cell death is given, although cell death caused by extracting chemicals from the coating is a possibility.

[0802] Qualitative cell viability test of the polymer solution or dispersion: Add 100 μL of the polymer solution or dispersion and 100 μL of DMEM medium to an Eppendorf tube and mix well with an oscillator for 30 minutes. For the polymer film, cut a fixed area of the film and disperse it in the medium for testing. Transfer the test fluid to a cell plate, and the cells are grown in a 37 °C / 95% RH CO₂ incubator for 48 - 96 hours. Record cell growth and morphology under a visible microscope.

[0803] Qualitative antiviral efficiency test of the polymer film: Drop 100 μL of virus fluid (5×10 7 / mL) onto the polymer film in a Petri dish. Cover the Petri dish for 30 minutes. Transfer the virus fluid to a cell plate, which contains 8×10 4 cells in 500 μL of medium in each well. Then rinse the film twice with 50 μL of DMEM medium, and combine the rinsing fluid with the previous test fluid in the same position in the plate. The total volume of the test fluid is 200 μL. Then incubate the cell plate in a 37 °C / 95% RH CO₂ incubator for 48 - 96 hours. Finally, record cell morphology and fluorescence under a UV microscope.

[0804] Qualitative antiviral efficiency test of the polymer solution or dispersion: Add 100 μL of virus fluid (5×10 7( / mL) and 100 μL of the polymer solution or dispersion were added to an Eppendorf and shaken well for 30 minutes using an oscillator. The test mixture was added to a cell plate that contained 8×10 4 cells in 500 μL of culture medium in each well. The cell plate was then incubated in a 37 °C / 95% RH CO2 incubator for 48 - 96 hours. Finally, cell morphology and fluorescence were recorded under a UV microscope.

[0805] Examples 1 - 4. Water-based coatings containing water-soluble polyethyleneimine intermediates

[0806] Table 2.

[0807]

[0808] Preparation of the aqueous phase:

[0809] 3.1 parts of HEC 380K ((2-hydroxyethylcellulose, average Mw = 380,000, from Aldrich)) was dissolved thoroughly in 96.9 parts of DI water. The pH of the solution was adjusted to 4.5 using a 5% solution of H3PO4.

[0810] Comparative Example 1: Preparation and antiviral activity evaluation

[0811] Preparation of the oil phase:

[0812] At 90 °C under nitrogen, 5.0 g (10.7 mmol) of thoroughly dried C18DMDEG was added to a solution of 7.67 g (16.03 mmol, 48 mmol reactive NCO) of N100 in 5 g of dry toluene, and the mixture was allowed to react for 15 hours. After removing toluene under reduced pressure, a clear viscous liquid (the first adduct) was obtained.

[0813] 4.144 parts of the first adduct (N100 - C18DMDEG(Br - )), 0.356 parts of PTMG 1000 (poly(tetramethylene glycol), average Mn = 1000, from Aldrich), and 1.5 parts of MEK (methyl ethyl ketone) were pre-reacted at 70 °C for 1 hour. The mixture was cooled to room temperature and dried under vacuum until the solid content reached approximately 90 wt%. 0.828 parts of polyisocyanate N100 (DESMODUR N100 from Convestro) and 1.276 parts of dry acetone were added to the solution and mixed uniformly.

[0814] Preparation of the oil-in-water emulsion and the coating

[0815] The aqueous solution prepared as above was added to the oil phase at room temperature and emulsified by sonication (100 W) for 10 seconds, performed 5 times, with a 10-second pulse between each sonication. The total emulsification time was about 90 - 120 seconds. The resulting oil-in-water emulsion was coated onto a 2-mil, corona-treated white PET (Melinex 339 from Teijin) and dried at room temperature for 10 minutes, followed by drying at 60 °C for 15 hours. The resulting film showed acceptable film properties and resistance to alcohol and water disinfection processes. As described above, its antiviral efficiency against adenovirus was measured by q-RT-PCR.

[0816] Examples 2 - 4

[0817] The same procedure described in Example 1 was repeated to prepare the emulsions and coatings of Examples 2, 3, and 4, except that the amount of the first adduct (N100 - C18DMDEG(Br-)) was reduced by 5 wt.%, and QPEI 37169, QPEI HB37169 (hyperbranched), or QPEI HB37478 was added in an amount of 5 wt.%.

[0818] Preparation of QPEI 37169

[0819]

[0820] QPEI 37169 was prepared as shown in the reaction scheme above.

[0821] For the chemical purposes described herein, as reported in the literature, the ratio of primary, secondary, and tertiary amines in branched PEI is assumed to be 1:2:1. 24,25

[0822] The procedure used was essentially as described by Gao et al. (2007). 26 The structure of QPEI 37169 is intended as an approximation, indicating that most primary and secondary amines have reacted with epoxides, and most tertiary amines have been quaternized by alkylation with benzyl chloride.

[0823] Under nitrogen, 3.33 g of a 70 kDa PEI solution (30% in water / 1 g PEI, assuming mw = 43.1 g / mol, 23.2 mmol) was added to a 25 mL two-necked flask and cooled to 0 °C. 5.4 g (92.8 mmol) of propylene oxide was added dropwise to this mixture at 0 - 3 °C. After the addition was complete, the reaction mixture was stirred at 0 - 3 °C for seven hours. Then the temperature of the reaction mixture was raised to 35 °C and the unreacted propylene oxide (about 3.60 mL) was distilled off. 11.75 g (10.6 mL, 92.8 mmol) of benzyl chloride was added to the resulting solution and the reaction solution was heated to 50 °C for 30 hours. The reaction solution was extracted with diethyl ether (3 × 20 mL) to remove unreacted benzyl chloride, residual propylene oxide, and lipophilic by-products or impurities (if any). The aqueous phase was separated and evaporated under vacuum and dried by lyophilization, leaving QPEI37169 (2.85 g) as a transparent solid. The product was characterized by proton NMR and infrared (IR) spectroscopy.

[0824] Preparation of QPEIHB37169

[0825] The same reaction in the preparation of QPEI 37169 was used for the preparation of QPEIHB37169 except that hyperbranched polyethyleneimine of the same molecular weight was used.

[0826] Preparation of QPEIHB37478

[0827] The same reaction in the preparation of QPEI 37169 was used for the preparation of QPEIHB37478 except that the quaternizing agent benzyl bromide was replaced by hexyl bromide and hyperbranched polyethyleneimine of the same molecular weight was used.

[0828] Even at a contact time as short as 30 seconds, replacing 5 wt.% of the first adduct (N100-C18DMDEG(Br-)) with three polyethyleneimine intermediates (QPEI) significantly improved the antiviral efficiency (see Table 2).

[0829] Examples 5 - 9. QPEI 37169 as a polyethyleneimine intermediate in the aqueous phase

[0830] Table 3.

[0831]

[0832] The compositions of Examples 5 - 9 were prepared using the same procedure as in Examples 1 - 4 except that the compositions were changed as shown in Table 3. All coatings showed acceptable film properties, water resistance, and alcohol resistance.

[0833] All coatings showed antiviral efficiency > 99.95% within a contact time of 30 minutes.

[0834] Examples 10 - 20 describe additional examples of polyethyleneimine intermediates or second adducts that can be used in the present technology.

[0835] Example 10. Synthesis of Polyethyleneimine Intermediate 40840

[0836]

[0837] A 500 mL three-neck round-bottom flask was equipped with a thermometer, condenser, and magnetic stirrer. The reaction flask was flushed with nitrogen, and the reaction was carried out under a nitrogen stream.

[0838] 10 g of PEI (70 kDa branched, 30 wt% aqueous solution, amine content 18 mmol / g solid polymer, ratio of primary, secondary, and tertiary amines = 1:2:1), potassium carbonate (37.07 g, 0.232 mol), and 150 mL of tert-amyl alcohol were added to the round-bottom flask. This mixture was stirred under nitrogen for 30 minutes and then 3-bromo-1-propanol (64.5 g, 0.464 mol, 1.3 equivalents for complete quaternization) was added dropwise at room temperature. The resulting mixture was heated and stirred at 95 °C for 96 hours.

[0839] After 96 hours, the mixture was cooled to room temperature and filtered to remove insoluble solids. The filtered solid was washed with 150 mL of methanol. The combined filtrate was treated with 250 mL of diethyl ether, and a white precipitate formed. The organic phase was decanted and the white solid was dissolved in 200 mL of methanol and precipitated with 200 mL of diethyl ether. This dissolution / precipitation process was carried out two more times, and the resulting white pasty solid was dried in a rotary evaporator and then further dried under high vacuum for 5 hours. The yield of the dry product was 17.4 g. The product was characterized by 1 1H NMR, and the degree of quaternization was analyzed using the Mohr argentometric titration method to measure the amount of bromide ions.

[0840] Example 11. Synthesis of Polyethyleneimine Intermediate 40660

[0841]

[0842] A 2-L three-neck round-bottom flask was equipped with a dropping funnel, condenser, and magnetic stirrer. The reaction flask was flushed with nitrogen, and the reaction was carried out under a nitrogen stream.

[0843] 10 g of PEI (branched, 70 kDa, 30 wt% aqueous solution, amine content 18 mmol / g of solid polymer, ratio of primary:secondary:tertiary amines = 1:2:1) was added to a reaction flask, and 835 mL of water was added thereto. 114.3 g of glycidyltrimethylammonium chloride (0.754 mol, approximately 4 equivalents for theoretical complete conversion) was dissolved in 130 mL of water and added dropwise to the reaction mixture. 153 g (210 mL, 1.5 mol) of triethylamine was added dropwise to the reaction mixture at room temperature. The resulting two-phase reaction mixture was stirred vigorously at room temperature for 4 days, after which the reaction mixture was a single clear phase. All solvents were removed in a rotary evaporator at 55 °C. The pasty liquid residue was dissolved in 200 mL of methanol, and the polymeric product was precipitated with 400 mL of diethyl ether. This methanol / diethyl ether dissolution and precipitation was repeated six times. The final precipitate was dried in a rotary evaporator and then 46.5 g of the final product was produced under high vacuum. The product was characterized by 1 1H NMR, and the degree of quaternization was analyzed using the Mohr argentometric titration method to measure the amount of chloride ions.

[0844] Example 12. Synthesis of Polyethyleneimine Intermediate 40818

[0845]

[0846] A 100-mL one-neck round-bottom flask was equipped with a condenser, a heating mantle, and a magnetic stirrer. The reaction flask was flushed with nitrogen, and the reaction was carried out under a nitrogen stream.

[0847] 2 g of glycidyl-functionalized PEI (3.3 mmol 13.3 mmol reactive N), bromohexane (7 g, 40 mmol, 3 equivalents), and 4.4 mL of tert-amyl alcohol were added to the flask, and the reaction mixture was heated at 96 °C for 96 h. The reaction mixture changed from colorless to light orange. The reaction was cooled to room temperature and the resulting solution was poured into tert-butyl methyl ether (TBME) with vigorous stirring such that a precipitate formed. The liquid was decanted from the precipitated solid and the solid was dissolved in methanol and reprecipitated with TBME. This process was repeated 3 times, and after drying in a rotary evaporator and then high vacuum, 4.06 g of product was produced. The product was characterized by 1 1H NMR, and the degree of quaternization was analyzed using the Mohr argentometric titration method to measure the amount of halide ions.

[0848] Example 13. Evaluation of Adenovirus Activity of Examples 10 and 11

[0849] As described above, the antiviral activities of aqueous solutions of polyethyleneimine intermediates 40840 and 40660 were evaluated.

[0850] Table 4.

[0851]

[0852] Example 14. Synthesis of a polyethyleneimine intermediate capped with a mono-isocyanate (approx. 85% free OH groups)

[0853] As shown below, the structure of the polymer product is intended as an approximation indicating that most of the hydroxyl groups (approx. 85% molar equivalent) have reacted with the blend of mono-isocyanates to form urethanes, with some hydroxyl groups remaining unreacted.

[0854]

[0855] The concentration of reactive hydroxyl groups (mmol / g of dry polymer) is determined by titrating a known amount (g) of dry hydroxyalkyl quaternary polyethyleneimine (HA-Q-PEI) with a known excess (g, mmol) of octadecyl isocyanate. The percentage of mono-isocyanate consumed in the reaction is determined by monitoring the reaction process using infrared (IR) spectroscopy to monitor the decrease in the isocyanate peak at 2263 cm -1 -1. Based on the percentage decrease of this peak, the millimoles of isocyanate consumed are estimated. This value is equivalent to the millimoles of polymer hydroxyl groups that have reacted with the isocyanate. In this way, the hydroxyl concentration of the polymer (mmol reactive hydroxyl / g dry polymer) is calculated and then used in subsequent reactions to determine the amount of mono-isocyanate required to functionalize a specific percentage of the reactive hydroxyl groups in the polymer. By doing so, the hydrophilic / hydrophobic properties of the polymer will be fine-tuned.

[0856] Using the procedure described in Example 2, 2.0 g (2.27 mmol, assuming a molecular weight of 881 g / mol for the polymer unit cell) of hydroxypropyl quaternary ammonium PEI, QPEI 37169, was prepared and then dried under vacuum at 60 °C for two hours, followed by storage overnight in a desiccator at room temperature. 13.8 g of tert-butanol and 9.2 g of dimethylacetamide were added to the dried polymer. The resulting mixture was stirred under nitrogen until the polymer was completely dissolved. Both solvents were dried using molecular sieves Fully dried. A mixture of 1.6 g (5.41 mmol) of octadecyl isocyanate and 0.36 g (2.32 mmol) of octyl isocyanate was added dropwise to the polymer solution. This mixture corresponds to a total of 7.73 mmol of monoisocyanate relative to approximately 85% of the available hydroxyl groups. The reaction mixture became slightly turbid. The resulting reaction mixture was stirred under nitrogen at room temperature for twelve hours. The resulting reaction mixture was filtered through a PTFE filter (1 μm pore size) to yield 20.83 g of capped QPEI 37169 as a 12.19% solids solution. IR spectroscopy showed that the expected new peaks corresponded to urethane carbonyls and that there were no residual isocyanate peaks.

[0857] In some embodiments, after the reaction with the monoisocyanate is complete, the reaction mixture is added to water to precipitate the capped product. This product is separated and washed with water to remove any water-soluble impurities and then dried for use in subsequent steps. This water precipitation step can be used to remove any water-soluble impurities that may cause toxicity.

[0858] Example 15. Process for the crosslinking and coating reaction of octadecyl carbamate / octyl carbamate quaternary PEI (Example of formation of the second adduct)

[0859] As shown below, the structure of polymer compound (A) is intended as an approximation to indicate that some of the unreacted hydroxyl groups of the capped QPEI 37169 have reacted with the polyisocyanate to form urethane crosslinks.

[0860]

[0861] Using the procedure described in Example 15, 20 g of octadecyl carbamate / octyl carbamate quaternary PEI was prepared, to which 1.25 g of Desmodur N 3300 (50% solution in anhydrous acetone) and 0.18 g of a 1% solution of dibutyltin dilaurate in dry toluene were added. The resulting mixture was thoroughly mixed and immediately coated onto a corona-pretreated white PET (2 mils, Milenex 339) supported by a stainless steel plate using a No. 36 Meyer rod. The coated film was heated in an oven at 60 °C for 30 minutes without vacuum. This dried film was used to measure the antimicrobial activity. IR spectroscopic analysis indicated no residual isocyanate.

[0862] It should be noted that the above crosslinking procedure was also carried out without the dibutyltin dilaurate catalyst and produced a reasonable coating, although the durability of the resulting dried film was slightly poorer than when using the catalyst.

[0863] Example 16. Antiviral efficiency of HA-Q-PEI polymers with different PEI molecular weights, nitrogen quaternary ammonium groups, and anion counterions against adenovirus in aqueous solution

[0864] Various HA-Q-PEI (hydroxyalkyl quaternary PEI) of the following formula:

[0865]

[0866] Prepared using a procedure similar to that described in Example 2 (preparation of QPEI 37169), and analyzed for its antiviral (AV) efficiency against adenovirus as described above. Selected data are shown in Table 5. (R1 = methyl for each polymer). These results show that within the range of PEI molecular weights and for different nitrogen quaternary ammonium groups (R2) and anion counterions (X-), the antiviral efficiency is very high.

[0867] Table 5.

[0868] Sample MW <![CDATA[R2]]> X- AV efficiency % 2-1； 600 n - hexyl Bromide ion 82 2-2 10,000 n - hexyl Bromide ion 97.29 2-3 100,000 n - hexyl Bromide ion 99.98 2-4 70,000 n - hexyl Bromide ion 99.93 2-5 70,000 Benzyl Chloride ion 99.9 2-6 70,000 Methyl Iodide ion 99.91 2-7 70,000 n - butyl Bromide ion 99.92 2-8 70,000 <![CDATA[-CH2C(O)OCH2CH3]]> Bromide ion 99.94 2-9 70,000 <![CDATA[-CH2C(O)Ph]]> Bromide ion 99.42

[0869] Example 17. Antiviral efficiency of HA-Q-PEI polymers with different PEI molecular weights against adenovirus in aqueous solution

[0870] Additional HA-Q-PEI polymers of the following formula with different molecular weights (R1 = methyl, R2 = hexyl, X = bromide ion):

[0871]

[0872] Prepared using a procedure similar to that described in Example 2 (preparation of QPEI 37169), and analyzed for its antiviral (AV) efficiency against adenovirus as described above. Selected data are shown in Table 6.

[0873] Table 6.

[0874] Sample MW (kDa) AV efficiency % 3-1 0.6 82.05 3-2 0.6 95.18 3-3 10 97.29 3-4 10 98.41 3-5 25 99.98 3-6 70 99.93 3-7 100 99.98 3-8 270 99.99 3-9 270 99.97

[0875] These results show that for this series of HA-Q-PEI polymers, the antiviral efficiency of the solution against adenovirus increases with increasing PEI molecular weight, within the range of 25,000 to 270,000, and levels off at >99% at the highest.

[0876] Although these HA-Q-PEI polymers exhibit high solution antiviral efficiency, due to their high water solubility, they are not directly suitable for making durable water-resistant surface coatings. Coating durability against solvents such as water and ethanol is highly desirable, such that the antimicrobial efficiency can be maintained even after cleaning the surface by washing, and the need for frequent re-disinfection of the surface is significantly reduced.

[0877] Example 18. Antiviral efficiency of the second adduct as an antimicrobial agent in a coating as a function of the weight percentage of the N100 crosslinker used

[0878] Coatings of the second adduct of the formula:

[0879]

[0880] Prepared using a procedure similar to that described in Example 15, substituting octadecyl carbamate / octyl carbamate quaternary ammonium PEI with HA-Q-PEI (prepared from PEI: molecular weight = 70,000 (branched), R1 = methyl, R2 = hexyl, X = bromide ion), and varying the crosslinker Z( N100):

[0881] ( amount of N100).

[0882] The antiviral efficiency of these second adducts against adenovirus was studied (procedure as described above). Selected data are shown in Table 7.

[0883] Table 7.

[0884] Sample wt.% of cross - linker * AV efficiency % 4-1 6.5 87.12 4-2 17.7 65.11 4-3 26.5 66.05 4-4 33.3 49.47 4-5 39.2 46.42 4-6 44.1 2.52

[0885] *Relative to wt. % of the second adduct

[0886] Crosslinking the HA-Q-PEI (polyethyleneimine intermediate) coating to form a polyurethane second adduct coating improved the water and ethanol durability of the coating, but as can be seen from this example, this was associated with a significant decrease in antiviral efficiency with increasing crosslinking amount.

[0887] Example 19. Antiviral efficiency of polyethyleneimine intermediates with or without monoisocyanate substitution as non-crosslinked coatings against adenovirus

[0888] Polyethyleneimine intermediates with monoisocyanate substitution (MUA-Q-PEI-A polymer, where R3 = C 18 alkyl or C8 alkyl) of the formula:

[0889]

[0890] Prepared from HA-Q-PEI (prepared from PEI: molecular weight = 70,000 (branched), R1 = methyl, R2 = benzyl) and a mixture of monoisocyanates (ratio of octadecyl isocyanate: octyl isocyanate = 7:3), where approximately 90% of the HA-Q-PEI hydroxyl groups react with the mixture of monoisocyanates (see the similar protocol in Example 14). The MUA-Q-PEI-A100 polymer was also prepared similarly, where approximately 100% of the HA-Q-PEI hydroxyl groups react with the mixture of monoisocyanates. As described above, the antiviral efficiency of the films of these MUA-Q-PEI-A and MUA-Q-PEI-A100 polymers against adenovirus was examined. The selected results are shown in Table 8.

[0891] Table 8.

[0892] Sample Polymer system Contact time (minutes) AV efficiency % 5-1 1% aqueous solution of HA - Q - PEI 30 97.41 5-2 Dry film MUA - Q - PEI - A 30 99.99 5-3 Dry film MUA - Q - PEI - A 1 99.84 5-4 Dry film MUA - Q - PEI - A 0.5 99.49 5-5 Dry film MUA - Q - PEI - A100 30 99.99 5-6 Dry film MUA - Q - PEI - A100 1 99.98 5-7 Dry film MUA - Q - PEI - A100 0.5 99.91

[0893] These results indicate that the high solution antiviral efficiency of the HA-Q-PEI polymer is maintained and / or enhanced after coating with the mixture of monoisocyanates to form the MUA-Q-PEI-A and MUA-Q-PEI-A100 polymers. These results also show that the coating exhibits >99% antiviral efficiency even at a contact time as short as 30 seconds.

[0894] Antiviral efficiency and coating durability of the second adduct coating against adenovirus as a function of the amount (weight percentage) of the N3300 polyisocyanate crosslinker used

[0895] The second adduct of the following formula (PUA-Q-PEI-B polymer, where R3 = C 18 alkyl or C8 alkyl):

[0896]

[0897] Prepared using a procedure similar to that described in Example 14. Specifically, HA-Q-PEI (prepared from PEI: molecular weight = 25,000 (hyperbranched), R1 = methyl, R2 = hexyl, X = bromide ion) was reacted with a mixture of monoisocyanates (ratio of octadecyl isocyanate: octyl isocyanate = 7:3), where approximately 90% of the HA-Q-PEI hydroxyl groups react with the mixture of monoisocyanates, and then the remaining hydroxyl groups were reacted with different amounts of crosslinker Z ( N3300):

[0898] ( N3300).

[0899] The antiviral efficiency (by the procedure described above) of the coatings of these PUA-Q-PEI-B polymers against adenovirus, water durability, and ethanol durability were evaluated. The general procedure for measuring water and ethanol durability was to immerse the cross-sectioned coating samples in water or ethanol for ten minutes, and then gently wipe the samples with a cotton swab. The intact coatings passed the test. The selected data are shown in Table 9.

[0900] Table 9.

[0901]

[0902]

[0903] * wt.% of crosslinker relative to the PUA-Q-PEI-B polymer product

[0904] These data indicate that the crosslinker is necessary to achieve good durability, and there is an optimal range of crosslinker levels for these samples, within which the antiviral efficiency > 99%, and beyond which the antiviral efficiency decreases significantly.

[0905] Example 21. Antibacterial and Antiviral Tests

[0906] Coating samples from Table 10 were prepared in a similar manner as described in Examples 1 - 4.

[0907] Table 10.

[0908]

[0909] QPEI:

[0910] C 18DMDEG:

[0911] The QPEI for these coatings was prepared as follows. 20 g of EPOMIN was added to a 500 mL four-neck round-bottom flask equipped with a reflux condenser, dropping funnel, thermometer, and a KPG stirrer with side stirrer blades. TMP-1050 (a polymer of PEI 70 kDa with an amine content of 18 mmol / g, where the ratio of primary amine:secondary amine:tertiary amine = 1:2:1), 150 ml of tert-amyl alcohol, and 32.1 g (232 mmol) of K2CO3. Under nitrogen, the mixture was stirred at 200 rpm at 25 °C to 30 °C for 30 minutes. At 25 - 30 °C, 6.5 g (46 mmol) of 3-bromo-1-propanol dissolved in 145.5 g (881 mmol) of 1-bromohexane was added dropwise to this reaction mixture over 30 minutes. After the addition was complete, the temperature was raised to 96 °C, and the reaction was stirred at 96 °C to 98 °C for 98 hours, yielding a light brown solution. The reaction solution was cooled to 25 - 30 °C and filtered (Büchner funnel), and the filter was washed with 50 ml of tert-amyl alcohol. The filtrate was concentrated to dryness under vacuum at below 50 °C, and 200 ml of diethyl ether was added to the residue at 25 - 30 °C. It was stirred for 30 - 60 minutes, during which a brown slurry formed. Stirring was stopped, and the solid was allowed to precipitate within 30 - 60 minutes. The supernatant was decanted. The decantation of the supernatant (ether suspension) was repeated several times (5 - 6 times) until the amount of alkyl halide in the decanted liquid was less than 0.5% by GC analysis. The residual liquid was distilled off from the solid under vacuum in a rotary evaporator at below 40 °C. The viscous off-white material was dissolved in methyl ethyl ketone at 25 - 30 °C, yielding a slightly turbid solution, which was filtered through a diatomaceous earth bed, after which a clear solution was observed. The solvent was distilled off under reduced pressure in a rotary evaporator at 45 °C to give a solid material. The solid material was dried at below 45 °C for 6 - 8 hours. The product, obtained as an off-white solid, was isolated in a yield of 39.4 g. Assuming that the alkylation rates between the two alkyl halides are similar, the theoretical molar % of PEI reacting with 1-bromopropanol and 1-bromohexane are 5% and 95%, respectively.

[0912] According to ISO standard 21702:2019, a range of tests on virus, bacteria, fungi, and microalgae were carried out on the coating samples from Table 10. The selected data are shown in Tables 11, 12, 13, and 14 below. Positive values reflect the percentage reduction of the microbial population. Negative log values indicate an increase in the microbial population.

[0913] Table 11.

[0914]

[0915]

[0916] Table 12.

[0917]

[0918]

[0919] Table 13.

[0920]

[0921] Table 14.

[0922]

[0923] The coating sample 3 from Table 10 was tested for antiviral and antibacterial efficiency after being subjected to wet abrasion (PAS standard 2424:2014, point 9.2.4) or dry abrasion (PAS standard 2424:2014, point 9.2.2). The data are shown in Table 15.

[0924] Table 15. Antimicrobial efficiency after wet and dry abrasion tests (coating sample 3)

[0925]

[0926] Non-limiting examples of QPEI that can be incorporated into the technology disclosed herein are described below.

[0927] Example 22. Compound 22-1

[0928] Compound 22-1 is similar to the QPEI samples 3-8 and 3-9 of Example 17 and is prepared from PEI with MW = 270 kDa. Compound 22-1 (batch number 105159) contains a ratio of nitrogen functionalization by hexyl halide to nitrogen functionalization by propylene oxide greater than 1:1 (i.e., there are more hexyl groups on the nitrogen atom than 2-hydroxypropyl groups). Compound 22-1 (batch number 99367) contains a ratio of nitrogen functionalization by hexyl halide to nitrogen functionalization by propylene oxide of approximately 1:1 (i.e., the number of hexyl groups on the nitrogen atom is approximately equal to the number of 2-hydroxypropyl groups).

[0929] Example 23. Compound 23-1

[0930] Compound 23-1 is similar to compound 37478 but is prepared from PEI with MW = 25 kDa. Compound 23-1 contains a ratio of nitrogen functionalization by hexyl halide to nitrogen functionalization by propylene oxide of approximately 1:1 (i.e., the number of hexyl groups on the nitrogen atom is approximately equal to the number of 2-hydroxypropyl groups).

[0931] Example 24. Compound 24-1

[0932] Compound 24-1 (Lot No. 109590) is similar to HB37478 of Example 4, but uses branched 70 kDa PEI instead of hyperbranched 70 kDa PEI. Compound 24-1 (Lot No. 109590) contains a ratio of nitrogen functionalization by hexyl halide to nitrogen functionalization by propylene oxide of approximately 1:1 (i.e., the number of hexyl groups on the nitrogen atom is approximately equal to the number of 2-hydroxypropyl groups).

[0933] Example 25. Compound 25-1

[0934] Compound 25-1 (Lot No. 105402 and Lot No. 109634) is similar to QPEI sample 2-9 of Example 16 (prepared from PEI with MW = 70 kDa). Compound 25-1 (Lot No. 105402 and Lot No. 109634) contains a ratio of nitrogen functionalization by benzoylmethyl halide to nitrogen functionalization by propylene oxide of approximately 1:1 (i.e., the number of benzoylmethyl groups on the nitrogen atom is approximately equal to the number of 2-hydroxypropyl groups).

[0935] Example 26. Compound 26-1

[0936] Compound 26-1 (Lot No. 109781) is similar to QPEI 37169 of Example 2 (prepared from PEI with MW = 70 kDa). Compound 26-1 (Lot No. 109781) contains a ratio of nitrogen functionalization by benzyl halide to nitrogen functionalization by propylene oxide of approximately 1:1 (i.e., the number of benzyl groups on the nitrogen atom is approximately equal to the number of 2-hydroxypropyl groups).

[0937] Example 27. Compound 27-1

[0938] Compound 27-1 (Lot No. 110417) is similar to Compound 25-1, but is prepared from PEI with MW = 750 kDa.

[0939] Example 28. Compound 28-1

[0940] Compound 28-1 (Lot No. 109831) is similar to polyethyleneimine intermediate 40660 of Example 11 (prepared from PEI with MW = 70 kDa).

[0941] Example 29. Compound 29-1

[0942] Compound 29-1 (Lot No. 110420) is similar to polyethyleneimine intermediate 40818 of Example 12 (prepared from PEI with MW = 70 kDa).

[0943] Example 30. Compound 30-1

[0944] Compound 30-1 corresponds to the intermediate compound in the synthesis of QPEI 37169 of Example 2 and is obtained by the reaction of PEI (MW = 70 kDa) with propylene oxide. Therefore, there is no quaternary amine in Compound 29-1.

[0945] Example 31. Compound 31-1

[0946]

[0947] A 1-L 3-neck round-bottom flask was equipped with a dropping funnel, condenser, water bath, and mechanical stirrer. The flask was flushed with nitrogen, and the reaction was carried out under a nitrogen stream.

[0948] A 50% aqueous solution of 20 g of 70 kDa branched PEI (10 g of PEI polymer, 0.180 mole amine content, where the ratio of primary:secondary:tertiary amines is approximately 1:2:1) was added to the flask and stirred at approximately 200 RPM. Note that theoretically, 0.180 mole of nitrogen content with this ratio of primary, secondary, and tertiary amines can react with 0.36 mole of alkyl halide. For this example, this is defined as "1 equivalent of alkyl halide".

[0949] tert-Amyl alcohol (150 ml) was added to the flask at ambient temperature, followed by K2CO3 (32.1 g, 0.232 mole). A mixture of bromopropanol (1.29 g, 0.0093 mole) and 1-bromohexane (151.86 g, 0.92 mole) (total alkyl halide = 0.93 mole, 2.6 equivalents, where the mole % content of each alkyl halide = 1% bromopropanol / 99% 1-bromohexane) was added dropwise over 1 - 2 hours at ambient temperature.

[0950] The reaction temperature was raised to 96 °C, and the reaction mixture was stirred at 96 °C for 98 hours. The reaction mixture was cooled to 25 - 30 °C, filtered, and the filtered material was washed with methanol (50 ml). The filtrate was evaporated to dryness under vacuum, keeping the temperature below 50 °C. Diethyl ether (200 ml) was added to the residue, and the mixture was stirred at room temperature for 30 - 60 minutes, after which a light brown slurry formed. The mixture was allowed to settle, and the supernatant was decanted. This diethyl ether trituration and decantation were repeated 3 - 4 times until the residual alkyl halide content in the decanted layer was less than 0.5%, as determined by GC analysis.

[0951] After completion of the grinding / decantation process, the mixture was evaporated to dryness under reduced pressure while maintaining the temperature below 40 °C, yielding an off-white viscous solid. This solid was dissolved in methyl ethyl ketone (100 ml) at 25 - 30 °C, filtered through diatomaceous earth, and the filtrate was evaporated to dryness at 45 °C under reduced pressure. The resulting solid was oven-dried at below 45 °C for 4 - 6 hours to give the product (37.8 g) as an off-white solid. The water content was measured by Karl-Fischer analysis to be 0.24%. The bromine content was measured by AgNO3 titration to be 23.6%. Assuming similar alkylation rates between the two alkyl halides, the theoretical molar % of PEI reacting with 1-bromopropanol and 1-bromohexane were 1% and 99%, respectively.

[0952] Example 32. Compound 32-1

[0953]

[0954] A 1-L 4-neck round-bottom flask was equipped with a dropping funnel, condenser, water bath, and mechanical stirrer. The flask was flushed with nitrogen, and the reaction was carried out under a nitrogen stream.

[0955] 10 g of 25 kDa hyperbranched PEI (0.180 molar amine content, where the ratio of primary:secondary:tertiary amines was approximately 1:1:1) was added to the flask together with water (10 ml). Note that theoretically, 0.180 molar nitrogen content with this ratio of primary, secondary, and tertiary amines can react with 0.36 moles of alkyl halide. For this example, this was defined as "1 equivalent of alkyl halide".

[0956] tert-Amyl alcohol (50 ml) was added to the flask at ambient temperature, and the suspension was stirred at 160 - 180 RPM. After stirring for 15 - 30 minutes, the mixture was cooled to 0 - 5 °C, and 1-bromopropanol (3.2 g, 0.023 mole, 0.064 equivalent) was added dropwise over 15 - 30 minutes at 0 - 5 °C. The reaction mixture was stirred at 0 - 5 °C for 4 - 5 hours, and then the temperature was raised to ambient temperature. The reaction solution was stirred at ambient temperature for 14 - 15 hours, after which the reaction mixture was a turbid solution.

[0957] The water content of the reaction solution was reduced by azeotropic distillation of the solvent (approx. 10 mL). This volume of tert-amyl alcohol was added to the reaction solution, and the distillation process was repeated 3 times. tert-Amyl alcohol was added to make up the original reaction solution volume, and the resulting mixture was stirred at 50 - 60 °C for 60 - 90 minutes, after which a clear solution was obtained.

[0958] Add a mixture of 1-bromooctadecane (232.1 g, 0.696 mol) and 1-bromooctane (44.8 g, 0.232 mol) (0.928 mol, 2.6 equivalents of alkyl halide) at 50 - 60 °C. Raise the temperature to 94 - 98 °C and stir the reaction solution at this temperature for 48 h to produce a clear brown solution. Remove the solvent under reduced pressure at a temperature below 60 °C, cool the resulting residue to 25 - 30 °C, and add 500 mL of acetone. Stir the resulting suspension at 25 - 30 °C for 30 - 60 min. Stop stirring and allow the suspension to settle for 1 h. Decant the supernatant from the solid, and add acetone (500 ml) to the solid residue. Stir this suspension at 25 - 30 °C for 30 - 60 min, then stop stirring and allow the suspension to settle within 30 - 60 min, and decant the supernatant from the settled solid. Repeat the stirring, settling, and decanting process several times until the 1-bromooctadecane and 1-bromooctane in the supernatant are less than 0.5%, as measured by GC analysis.

[0959] Remove the remaining solvent under reduced pressure at a temperature below 35 °C. Further dry the solid product at a temperature below 35 °C for 8 - 10 h to produce 40.6 g of the QPEI product as a light brown solid. The bromine content was determined to be approximately 23%, as measured by AgNO3 titration. The theoretical molar percentages for reaction with a 75 / 25 mixture of 1-bromopropanol, 1-bromooctadecane, and 1-bromooctane are 6.4% and 93.6%, respectively.

[0960] Example 33. Compound 33-1

[0961]

[0962] A 0.5-L 4-neck round-bottom flask is equipped with a dropping funnel, condenser, water bath, and mechanical stirrer. Flush the flask with nitrogen, and the reaction is carried out under a nitrogen stream.

[0963] Add 10 g of 25 kDa hyperbranched PEI (0.180 mol amine content, where the ratio of primary:secondary:tertiary amines is approximately 1:1:1) to the flask and stir at 160 - 180 RPM. Note that theoretically, 0.180 mol of nitrogen content with this ratio of primary, secondary, and tertiary amines can react with 0.120 mol of ε-caprolactone (for this example, "1 equivalent of ε-caprolactone") and 0.360 mol of 1-bromohexane (for this example, "1 equivalent of 1-bromohexane").

[0964] Add water (10 g) together with tert-amyl alcohol (50 ml) to the flask, and cool the resulting solid suspension to 0 - 5 °C.

[0965] Caprolactone (2.65 g, 0.0238 mol, 0.2 eq) was added dropwise at 0 - 5 °C over 15 - 30 minutes. The resulting mixture was stirred at 0 - 5 °C for 4 - 5 hours. The temperature was raised to 25 - 30 °C and the reaction solution was stirred at this temperature for 14 - 15 hours, resulting in a turbid solution.

[0966] tert-Amyl alcohol was distilled off to remove water from the reaction mixture by azeotropy, and fresh tert-amyl alcohol was added to replace the distilled solvent. The reaction temperature was raised to 50 - 60 °C and the reaction solution was stirred for 60 - 90 minutes, resulting in a clear solution. 1-Bromohexane (153.2 g, 0.928 mol, 2.6 eq) was added. The resulting reaction mixture was stirred at 50 - 60 °C for 15 - 30 minutes and then the temperature was raised to 94 - 98 °C. The reaction solution was stirred at this temperature for 48 hours, resulting in a solid suspension.

[0967] The reaction solution was cooled to 25 - 30 °C. Diethyl ether (100 ml) was added dropwise and the resulting suspension was stirred at 25 - 30 °C for 30 - 60 minutes. Stirring was stopped and the suspension was allowed to settle for 1 hour. The supernatant was decanted from the settled solid and fresh diethyl ether (100 ml) was added. This suspension stirring, settling, and decanting process was repeated several times until the 1-bromohexane content in the decanted liquid was less than 0.5%, as measured by GC analysis.

[0968] The remaining solvent was removed under reduced pressure at below 35 °C. The crude solid product was further dried at below 35 °C for 10 - 12 hours to obtain the QPEI product (32 g) as a beige solid. The water content was measured to be 1200 PPM, as measured by Karl Fischer analysis. The bromine content was determined to be approximately 35%, as measured by AgNO3 titration.

[0969] Assuming that caprolactone reacts mainly with primary amines, the theoretical molar % of PEI reacting with caprolactone and 1-bromohexane are approximately 7% and 93%, respectively.

[0970] Example 34. Additional QPEI Compounds

[0971] The following compounds were prepared using a procedure similar to the procedure in the examples described above.

[0972]

[0973] *Indicates the molecular weight of the polyethyleneimine precursor

[0974] **Indicates the stoichiometric ratio

[0975] Example 35. Antimicrobial Activity Study

[0976] Minimum Inhibitory Concentration (MIC)

[0977] The antimicrobial efficacy of the tested compounds was studied using the standard broth microdilution method. In sterile MH broth in a 96-well plate, serial two-fold dilutions of each compound were prepared in a concentration range from 100 μM to 0.8 μM. The ONC of each bacterial strain was adjusted to obtain a standard bacterial concentration (5×10 5 CFU / mL), and it was added to each dilution to determine the MIC in a total volume of 100 μL of MH broth. All plates were incubated statically at 37 °C for 24 hours. Sterile dH2O was used only as a vehicle control, including positive (bacteria only) and negative (MH medium only) controls for each bacterial strain. To determine the MIC breakpoint, the plates were stained with 10 μL of 0.02% resazurin and incubated at 37 °C for 30 minutes. After incubation, all plates were imaged, and the absorbance at 570 nm (plate reader) was measured. The MIC was defined as the lowest concentration of the compound that inhibited growth. For all tested compounds, MH medium was used as a negative control, and only bacteria were used as a positive control on each plate. Serial two-fold dilutions were made by mixing 50 μL of the highest concentration (x2) from rows A to H containing 50 μL of sterile MH broth.

[0978] MIC Data Analysis

[0979] The data was exported to Microsoft Excel, and background normalization was performed by subtracting the OD570nm value from the wells containing only the medium (-VE control). The MIC value was determined by plotting the OD570nm value (Y) against the logarithmic concentration (X) of each compound. The data was fitted using the modified Gompertz model to obtain a more accurate MIC. The average OD570nm of each tested compound concentration was fitted to an S-shaped curve using the modified Gompertz function (y = A + Ce - e(B(x - M))), and the minimum inhibitory concentration (MIC) was identified from the inflection point of the lower asymptote (GraphPad Prism 9.0). This was applied to the mean of three biological replicates for each dilution in each compound, where each biological replicate had four technical replicates (n = 12).

[0980] Minimum Bactericidal Concentration (MBC) Procedure

[0981] To determine the MBC compound concentration, the breakpoint was estimated based on the MIC curve. As described above, all bacterial strains were cultured overnight. The next day, the overnight culture was adjusted to produce 5×10 5A cell density of cells / mL. Briefly, the culture was adjusted to the McFarland standard (0.08 - 0.12) and diluted (1:150). The adjusted culture was inoculated into a 96-well plate containing 50 μL of sterile Muller-Hinton broth (MHB) and two concentrations of each compound. The MBC plates were incubated statically at 37 °C for 24 hours. Sterile dH2O was used as a vehicle control, and positive controls (bacteria only) and negative controls (media only) were also included in the assay. The MBC cultures were quantified by serial dilution in a 96-well plate and spot plating onto Muller-Hinton agar (MHA). The MHA plates were incubated at 37 °C for 24 hours and counted. The results are presented as CFU / mL.

[0982] Summary of results:

[0983] Table 16. Summary of MIC values of compounds tested against the listed bacteria. All values are in μM.

[0984]

[0985]

[0986] * Compound 39637 corresponds to Corresponds to.

[0987] ** Compound 40598 corresponds to Corresponds to.

[0988] *^ Compound 40597 corresponds to Corresponds to.

[0989] Table 17. Summary of MBC values of compounds tested against the listed bacteria. All values are in μM.

[0990]

[0991] Compounds 39637, 40598, and 40597 are as defined in Table 15.

[0992] -: No activity was observed

[0993] Compounds 25-1 (lot numbers 105402 and 109634), 39637 (lot numbers 105543 and 109466), 24-1 (lot number 109590), 23-1 (lot number 109770), and 26-1 (lot number 109781) showed strong antimicrobial activity against the Gram +ve species Enterococcus faecalis and Staphylococcus aureus.

[0994] Among Gram-negative species (Klebsiella pneumoniae and Pseudomonas aeruginosa), three compounds were able to show inhibitory effects within the concentration ranges studied: compound 22-1 (lot number 105159), 22-1 (lot number 99367), and 24-1 (lot number 109590).

[0995] Compound 39637 (lot numbers 105543 and 109466), 24-1 (lot number 109590), and 23-1 (lot number 109770) inhibited Staphylococcus aureus at concentrations from 1.57 μM to 6.25 μM.

[0996] Among all the compounds tested, the most effective MIC and MBC were lower in Gram-positive bacteria; however, at much higher concentrations, Gram-negative bacteria did seem to have broad-spectrum activity.

[0997] Compound 22-1 (lot numbers 105159 and 99367) showed the most effective MBC inhibition curves across all bacterial strains. The MBC values clearly showed that all strains were inhibited at relatively low concentrations.

[0998] Among all the compounds tested above, the following compounds showed the lowest antimicrobial activity: compound 40840 (lot number 110435), 40598 (lot number 109448), 30-1 (lot number 109666), 28-1 (lot number 109831), and 40597 (lot number 109444). Compound 27-1 (lot number 110417) showed low antimicrobial efficacy by MIC, but inhibited five out of seven strains at 6.25 μM in MBC.

[0999] Additional compounds were tested to obtain MIC values against the same bacteria shown in Tables 16 and 17 (see Table 18). ****: For all bacteria tested, the MIC of QPEI ≤ 12.5 μM; ***: For > 50% of the bacteria tested, the MIC of QPEI > 12.5 μM and the MIC of QPEI ≤ 50 μM; **: For < 50% of the bacteria tested, the MIC of QPEI > 12.5 μM and the MIC of QPEI ≤ 50 μM; *: For all bacteria tested, the MIC of QPEI > 100 μM.

[1000] Table 18.

[1001]

[1002]

[1003] References:

[1004] ________________

[1005] 1 Ellingson, K.D. et al. (2020). “Urban Hospital Study–Antimicrobial Surface Coating.” *Clinical Infectious Diseases*, 71(8): 1807-1813.

[1006] 2 Jarach, N. et al., (2020). “Polymers in the Medical Antiviral Front-Line”. *Polymers*, 12(8): 1727.

[1007] 3 *The Merck Manual of Diagnosis and Therapy*, (2011). 19th Edition, published by Merck Sharp & Dohme Corp. (ISBN 978-0-911910-19-3).

[1008] 4 *Encyclopedia of Molecular Cell Biology and Molecular Medicine*, edited by Robert S. Porter et al., published by Blackwell Science Ltd., 1999-2012 (ISBN 9783527600908).

[1009] 5 *Molecular Biology and Biotechnology: A Comprehensive Desk Reference*, (1995). Edited by Robert A. Meyers, published by VCH Publishers, Inc. (ISBN 1-56081-569-8).

[1010] 6 *Immunology*, (2006). Werner Luttmann, published by Elsevier.

[1011] 7Janeway's Immunobiology, (2014). Kenneth Murphy, Allan Mowat, Casey Weaver (Eds.), Taylor & Francis Limited, (ISBN 0815345305, 9780815345305).

[1012] 8 Lewin's Genes XI, (2014). Published by Jones & Bartlett Publishers (ISBN-1449659055).

[1013] 9 Michael Richard Green and Joseph Sambrook, (2012). Molecular Cloning: A Laboratory Manual, 4th Edition, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y., USA (ISBN 1936113414).

[1014] 10 Davis et al., (2012). Basic Methods in Molecular Biology, Elsevier Science Publishing, Inc., New York, USA (ISBN 044460149X).

[1015] 11 Laboratory Methods in Enzymology: DNA, (2013). Jon Lorsch (Ed.) Elsevier (ISBN 0124199542).

[1016] 12 Current Protocols in Molecular Biology (CPMB), (2014). Frederick M. Ausubel (Ed.), John Wiley and Sons (ISBN 047150338X, 9780471503385).

[1017] 13 Current Protocols in Protein Science (CPPS), (2005). John E. Coligan (Ed.), John Wiley and Sons

[1018] 14 Current Protocols in Immunology (CPI) (2003). Coligan, J. E. et al., (Eds.). John Wiley & Sons (ISBN 0471142735, 9780471142737).

[1019] 15 Ikonen, N. et al., (2018). “Deposition of respiratory virus pathogens on frequently touched surfaces at airports.” BMC Infectious Diseases, 18(437): 1 - 8.

[1020] 16 Géczi, Z. et al., (2018). “Antimicrobial Silver - Polyethyleneimine Polylactic Acid Polymer Composite Film for Coating Methacrylate - Based Denture Surfaces.” J. of Nanomaterials, 2018(6): 1 - 9.

[1021] 17 Park, D. et al., (2006). “One - Step, Painting - Like Coating Procedures To Make Surfaces Highly and Permanently Bactericidal.” Biotechnology Prog. 22(2): 584 - 589.

[1022] 18Xue, Y. and Xiao, H. (2015). “Antibacterial / Antiviral Property and Mechanism of Dual-Functional Quaternized Pyridinium-Type Copolymer.” Polymers, 7(11): 2290 - 2303.

[1023] 19 U.S. Patent No. 5,783,502, “Virus Inactivating Coatings.” (issued on July 21, 1998).

[1024] 20 Nurdin, N. et al., (1993). “Biocidal Polymers Active By Contact. II. Biological Evaluation of Polyurethane Coatings with Pendent Quaternary Ammonium Salts.” J. of Applied Polymer Science, 50: 663 - 670.

[1025] 21 Chung, S. et al., (2016). “Antimicrobial Nanostructural Polyurethane Scaffolds.” Chapter 17, ADVANCES IN POLYURETHANE BIOMATERIALS, Cooper S.L and Guan, J. (eds.), Elsevier Publishing Company.

[1026] 22 Park, D. et al., (2013). “Antiviral and Antibacterial Polyurethanes of Various Modalities.” Appl. Biochem. Biotechnol., 169: 1134 - 1146.

[1027] 23Gao, B. et al. (2007). “Studies on the Preparation and Antibacterial Properties of Quaternized Polyethyleneimine.” J. Biomaterials Science, Polymer Edition, 18(5): 531 - 544.

[1028] 24 Klibanov, A. et al. (2006). “One - Step Painting - Like Coating Procedures to make Surfaces Highly and Permanently Bactericidal.” Biotechnol. Prog., 22(2): 584 - 589.

[1029] 25 Gao, B. et al. (2007). “Studies on the Preparation and Antibacterial Properties of Quaternized Polyethyleneimine.” J. Biomaterials Science, Polymer Edition, 18(5): 531 - 544.

[1030] 26 Ibid.

[1031] All patents and other publications cited throughout this application, including reference documents, issued patents, published patent applications, and co - pending patent applications, are hereby expressly incorporated by reference herein to describe and disclose, for example, the methods described in these publications that can be used in conjunction with the technologies described herein. These publications are provided solely for their disclosure prior to the filing date of this application. Nothing in this regard shall be construed as an admission that the inventors are entitled to antedate such disclosure by virtue of prior invention or for any other reason. All statements as to the date or content of these documents are based on information available to the applicant and do not constitute any admission as to the correctness of the date or content of these documents.

[1032] The foregoing written description is considered to be sufficient to enable a person skilled in the art to practice aspects and embodiments of the present invention. The aspects and embodiments of the present invention are not limited by the scope of the provided examples, as these examples are intended to be a single illustration of one aspect, and other functionally equivalent embodiments are within the scope of the present disclosure. Various modifications will be apparent to those skilled in the art from the foregoing description and fall within the scope of the appended claims. The advantages and objectives described herein are not necessarily covered by each embodiment. Using only routine experimentation, a person skilled in the art will recognize or be able to ascertain many equivalent forms of the specific embodiments described herein. Such equivalent forms are intended to be covered by the appended claims.

Claims

1. An antimicrobial composition comprising an oil-in-water emulsion, said oil-in-water emulsion comprising: (i) an oil phase, said oil phase comprising a first polyfunctional crosslinker and a first adduct of a first quaternary ammonium salt, wherein said first quaternary ammonium salt has a reactive linking group to react with said first polyfunctional crosslinker; optionally a polyol; a polyethyleneimine intermediate or a second adduct of said polyethyleneimine intermediate and a second polyfunctional crosslinker; and optionally a third polyfunctional crosslinker; and (ii) an aqueous phase, said aqueous phase comprising a water-soluble polymer, wherein said polyethyleneimine intermediate comprises an optionally substituted hydroxyalkylene functional group, said optionally substituted hydroxyalkylene functional group reacting with said first adduct and, if present, said second polyfunctional crosslinker; and at least a portion of the nitrogen atoms present in said polyethyleneimine intermediate are quaternized.

2. The antimicrobial composition according to claim 1, wherein said water-soluble polymer is crosslinked with: (a) said first polyfunctional crosslinker incorporated in said first adduct; (b) said second polyfunctional crosslinker incorporated in said second adduct, when present; (c) said third polyfunctional crosslinker, when present; or (d) any combination of two or more of them.

3. The antimicrobial composition according to claim 1 and claim 2, wherein the first quaternary ammonium salt has a chemical structure of, wherein R 1 selected from the group consisting of: -(C8-C 30 alkyl), -(C8-C 30 heteroalkyl), -(C8-C 30 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl), -(C6-C 10 aryl)-(C8-C 30 alkyl), -(C6-C 10 aryl)-(C8-C 30 heteroalkyl), -(CR m R n ) x10 -W 10 -(CR p R q ) y10 -H and -(CR m R n ) x11 -W 11 -(CR p R q ) y11 H-; wherein -(C8-C 30 heteroalkyl), -(C8-C 30 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl)-(C8-C 30 heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S and Si; R 2 selected from the group consisting of: -(C1-C4 alkyl), -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl), -(C6-C 10 aryl)-(C1-C4 alkyl), -(C6-C 10 aryl)-(C1-C4 heteroalkyl), -(CR m R n ) x20 -W 20 -(CR p R q ) y20 -H and -(CR m R n ) x21 -W 21 -(CR p R q ) y21 -H; wherein -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl)-(C1-C4 heteroalkyl) have 1 to 2 heteroatoms independently selected from O, S and Si; R 3 selected from the group consisting of: -(C1-C 30 alkyl), -(C1-C 30 heteroalkyl), -(C1-C 30 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl), -(C6-C 10 aryl)-(C1-C 30 alkyl), -(C6-C 10 aryl)-(C1-C 30 heteroalkyl); -(CR m R n ) x30 -W 30 -(CR p R q ) y30 -H and -(CR m R n ) x31 -W 31 -(CR p R q ) y31 -H; wherein -(C1-C 30 heteroalkyl), -(C1-C 30 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl)-(C1-C 30 heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S and Si; A is a linking group selected from the group consisting of: -(C3-C 20 alkylene)-, -(C3-C 20 heteroalkylene)-, -(C6-C 10 arylene)-(C3-C 20 alkylene)-, -(CR m R n ) x40 -W 40 -(CR p R q ) y40 - and -(CR m R n ) x41 -W 41 -(CR p R q ) y41 -, where -(C3-C 20 heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; and -(C3-C 20 alkylene)- and -(C3-C 20 heteroalkylene)- are optionally substituted with 1 to 6 substituents independently selected from the following: -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl); Each R m , R n , R p and R q is independently selected from H and C1-C4 alkyl; W 10 、W 20 、W 30 and W 40 are independently selected from -C(O)-; -C(O)O-; -OC(O)-; -C(O)NH-; and -NHC(O)-; W 11 、W 21 、W 31 and W 41 are independently selected from 5- to 6-membered cycloalkyl, C6-C 10 aryl, 5- to 6-membered heteroalkyl and 5- to 6-membered heteroaryl, wherein the heteroalkyl contains 1-2 ring heteroatoms selected from O, N, S and Si; and the heteroaryl contains 1-3 ring heteroatoms selected from O, N, S and Si; x10 is an integer from 1 to 30, and y10 is an integer from 0 to 29, where 8 ≤ (x10 + y10) ≤ 30; x11 is an integer from 1 to 30, and y11 is an integer from 0 to 29, where 8 ≤ (x11 + y11) ≤ 30; x20 is an integer from 1 to 4, and y20 is an integer from 0 to 3, where x20 + y20 ≤ 4; x21 is an integer from 1 to 4, and y21 is an integer from 0 to 3, where x21 + y21 ≤ 4; x30 is an integer from 1 to 30, and y30 is an integer from 0 to 29, where x30 + y30 ≤ 30; x31 is an integer from 1 to 30, and y31 is an integer from 0 to 29, where x31 + y31 ≤ 30; x40 is an integer from 1 to 19, and y40 is an integer from 1 to 19, where 3 ≤ (x40 + y40) ≤ 20; x41 is an integer from 1 to 20, and y41 is an integer from 0 to 19, where 3 ≤ (x41 + y41) ≤ 20; Y is selected from the group consisting of: -OH, -NHR 4 , -SH, -CO2H, -C(O)NHR 4 , -C(S)NHR 4 , Each R 4 is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl), where -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si; and X - Independently an acetate ion, a halide ion, a sulfate ion, a sulfonate ion, a phosphate ion, a phosphonate ion, a carbonate ion, a silicate ion, a hexafluorophosphate ion, a hexafluoroantimonate ion, a trifluoromethanesulfonate ion, a borate ion, or an organic-substituted derivative of any of the foregoing.

4. The antimicrobial composition according to claim 3, wherein R 1 is selected from the group consisting of: -(C 12 -C 30 -alkyl), -(C 12 -C 30 -heteroalkyl), -(C 12 -C 30 -alkyl)-(C6-C 10 -aryl), -(C 12 -C 30 -heteroalkyl)-(C6-C 10 -aryl), -(C6-C 10 -aryl)-(C 12 -C 30 -alkyl) and -(C6-C 10 -aryl)-(C 12 -C 30 -heteroalkyl); wherein -(C 12 -C 30 -heteroalkyl), -(C 12 -C 30 -heteroalkyl)-(C6-C 10 -aryl) and -(C6-C 10 -aryl)-(C 12 -C 30 -heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S, and Si.

5. The antimicrobial composition according to claim 3 or claim 4, wherein R 3 is selected from the group consisting of: -(C1-C4 alkyl), -(C1-C4 heteroalkyl), -(C1-C4 alkyl)-(C6-C 10 aryl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl)-(C1-C4 alkyl), and -(C6-C 10 aryl)-(C1-C4 heteroalkyl); wherein -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl)-(C1-C4 heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S, and Si.

6. The antimicrobial composition according to any one of claims 3 to 5, wherein R 2 and R 3 are methyl.

7. The antimicrobial composition according to any one of claims 3 to 6, wherein A is -(CH2) m - or -(CH2CHR 5 -O-) n CH2CHR 5 -, where m is an integer from 2 to 20; n is 0, 1, 2, 3, 4 or 5; and each R 5 is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl), wherein -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S and Si.

8. The antimicrobial composition according to claim 7, wherein each R 5 is independently H or methyl.

9. The antimicrobial composition according to any one of claims 1 to 8, wherein the first quaternary ammonium salt or a combination of two or more of them.

10. The antimicrobial composition according to any one of claims 1 to 9, wherein based on the dry weight of the oil phase, said first quaternary ammonium salt is present in said oil phase in an amount of about 1 wt% to about 50 wt%.

11. The antimicrobial composition according to any one of claims 1 to 10, wherein based on the dry weight of the oil phase, said first quaternary ammonium salt is present in said oil phase in an amount of about 5 wt% to about 25 wt%.

12. The antimicrobial composition according to any one of claims 1 to 12, wherein based on the dry weight of the oil phase, said first polyfunctional crosslinker incorporated into said first adduct is present in said oil phase in an amount of about 2 wt% to about 25 wt%.

13. The antimicrobial composition according to any one of claims 1 to 13, wherein based on the dry weight of the oil phase, the first polyfunctional crosslinking agent incorporated into the first adduct is present in the oil phase in an amount of about 5 wt% to about 20 wt%.

14. The antimicrobial composition according to any one of claims 1 to 14, wherein based on the dry weight of the oil phase, the second polyfunctional crosslinking agent incorporated into the second adduct is present in the oil phase in an amount of about 0.1 wt% to about 10 wt%.

15. The antimicrobial composition according to any one of claims 1 to 15, wherein based on the dry weight of the oil phase, the second polyfunctional crosslinking agent incorporated into the second adduct is present in the oil phase in an amount of about 2 wt% to about 8 wt%.

16. The antimicrobial composition according to any one of claims 1 to 16, wherein based on the dry weight of the oil phase, the third polyfunctional crosslinking agent is present in the oil phase in an amount of about 0.1 wt% to about 20 wt%.

17. The antimicrobial composition according to any one of claims 1 to 17, wherein based on the dry weight of the oil phase, the third polyfunctional crosslinking agent is present in the oil phase in an amount of about 2 wt% to about 15 wt%.

18. The antimicrobial composition according to any one of claims 1 to 17, wherein the first polyfunctional crosslinking agent is a first polyisocyanate; the second polyfunctional crosslinking agent, when present, is a second polyisocyanate; the third polyfunctional crosslinking agent, when present, is a third polyisocyanate; and the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate are different.

19. The antimicrobial composition according to any one of claims 1 to 17, wherein the first polyfunctional crosslinking agent is a first polyisocyanate; the second polyfunctional crosslinking agent, when present, is a second polyisocyanate; the third polyfunctional crosslinking agent, when present, is a third polyisocyanate; and the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate are the same.

20. The antimicrobial composition according to claim 18 or claim 19, wherein the average isocyanate functionality of each of the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate is 2 to 5.

21. The antimicrobial composition according to claim 20, wherein the average isocyanate functionality of each of the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate is 3 to 4.

22. The antimicrobial composition according to any one of claims 18 to 21, wherein each of the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate is prepared from a diisocyanate independently selected from the group consisting of: hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), trimethylhexamethylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

23. The antimicrobial composition according to any one of claims 18 to 21, wherein each of the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate is independently selected from the group consisting of: N-3300, N-100, Z4470SN, T series polyisocyanates and M series polyisocyanates.

24. The antimicrobial composition according to any one of claims 18 to 23, wherein the average isocyanate functionality of the first adduct is from 2 to 3.

25. The antimicrobial composition according to claim 24, wherein the average isocyanate functionality of the first adduct is from about 2.05 to about 2.

3.

26. The antimicrobial composition according to any one of claims 18 to 25, wherein the reactive isocyanate functional groups on the first adduct are protected with a blocking agent.

27. The antimicrobial composition according to claim 26, wherein the blocking agent is selected from the group consisting of: oximes, phenols, malonic esters, alcohols, lactams, dicarbonyl compounds, isohydroxamic acid esters, bisulfite addition compounds, hydroxylamines, esters of p-hydroxybenzoic acid, and salicylic acid.

28. The antimicrobial composition according to claim 27, wherein the blocking agent is selected from the group consisting of: acetone oxime, methyl ethyl ketone oxime, sodium bisulfite, diethyl malonate, and 3,5-dimethylpyrazole.

29. The antimicrobial composition according to any one of claims 25 to 28, which further comprises a deblocking agent.

30. The antimicrobial composition according to claim 29, wherein the deblocking agent is selected from the group consisting of: organotin, organobismuth, and tertiary amines.

31. The antimicrobial composition according to any one of claims 1 to 30, wherein based on the dry weight of the oil phase, the first adduct is present in the oil phase in an amount of from about 5 wt% to about 70 wt%.

32. The antimicrobial composition according to any one of claims 1 to 31, wherein based on the dry weight of the oil phase, the second adduct is present in the oil phase in an amount of from about 1 wt% to about 30 wt%.

33. The antimicrobial composition according to any one of claims 1 to 32, wherein based on the dry weight of the oil phase, the second adduct is present in the oil phase in an amount of from about 3 wt% to about 15 wt%.

34. The antimicrobial composition according to any one of claims 1 to 33, wherein the oil phase further comprises an organic solvent or a diluent.

35. The antimicrobial composition according to claim 34, wherein the organic solvent or diluent in the oil phase is water-miscible.

36. The antimicrobial composition according to claim 34 or claim 35, wherein the organic solvent or diluent is acetone.

37. The antimicrobial composition according to any one of claims 34 to 36, wherein based on the weight of the oil phase, the organic solvent or diluent is present in the oil phase in an amount of about 5 wt% to about 35 wt%.

38. The antimicrobial composition according to any one of claims 34 to 37, wherein based on the weight of the oil phase, the organic solvent or diluent is present in the oil phase in an amount of about 10 wt% to about 30 wt%.

39. The antimicrobial composition according to any one of claims 1 to 38, wherein the polyol, when present, is selected from the group consisting of polyether polyols, polyester polyols, polyacrylic acid polyols, polymethacrylic acid polyols, polycaprolactone polyols, polybutadiene polyols, poly(acrylonitrile-co-butadiene) polyols, polysiloxane polyols, copolymers of any two or more thereof, and combinations of any two or more thereof.

40. The antimicrobial composition according to claim 39, wherein the polyol is selected from the group consisting of poly(tetramethylene glycol), polyethylene glycol, polypropylene glycol, poly(ethylene glycol-b-propylene glycol-b-ethylene glycol), and poly(propylene glycol-b-polyethylene glycol-b-propylene glycol).

41. The antimicrobial composition according to claim 39 or claim 40, wherein the polyol has a weight average molecular weight of about 300 to about 3000.

42. The antimicrobial composition according to any one of claims 39 to 41, wherein the polyol has a weight average molecular weight of about 400 to about 2000.

43. The antimicrobial composition according to any one of claims 39 to 42, wherein the polyol has a weight average molecular weight of about 600 to about 1500.

44. The antimicrobial composition according to any one of claims 1 to 43, wherein based on the dry weight of the oil phase, the polyol is present in the oil phase in an amount of about 1 wt% to about 40 wt%.

45. The antimicrobial composition according to any one of claims 1 to 44, wherein based on the dry weight of the oil phase, the polyol is present in the oil phase in an amount of about 5 wt% to about 25 wt%.

46. The antimicrobial composition according to any one of claims 1 to 45, wherein the water-soluble polymer is selected from the group consisting of hydroxyethyl cellulose (HEC), hydroxypropyl cellulose, polyvinyl alcohol, poly(hydroxyethyl methacrylate-co-alkyl methacrylate), poly(hydroxyethyl methacrylate-co-alkyl acrylate), poly(hydroxyethyl acrylate-co-alkyl methacrylate), poly(hydroxyethyl acrylate-co-alkyl acrylate), polyacrylamide, polyethyleneimine intermediate, copolymers of two or more thereof, copolymers of one or more thereof with polyvinylpyrrolidone poly(glycidyl acrylate) or with poly(glycidyl methacrylate), and combinations or blends of two or more thereof.

47. The antimicrobial composition according to any one of claims 1 to 45, wherein the water-soluble polymer is hydroxyethyl cellulose or a hydrophobically modified derivative thereof.

48. The antimicrobial composition according to any one of claims 1 to 45, wherein the water-soluble polymer is a polyethyleneimine intermediate.

49. The antimicrobial composition according to any one of claims 1 to 48, wherein the water-soluble polymer is present in the aqueous phase in an amount of about 0.5 wt% to about 15 wt% based on the dry weight of the oil phase.

50. The antimicrobial composition according to any one of claims 1 to 49, wherein the water-soluble polymer is present in the aqueous phase in an amount of about 3 wt% to about 12 wt% based on the dry weight of the oil phase.

51. The antimicrobial composition according to any one of claims 1 to 50, wherein the water-soluble polymer is present in the aqueous phase in an amount of about 5 wt% to about 10 wt% based on the dry weight of the oil phase.

52. The antimicrobial composition according to any one of claims 1 to 51, wherein the aqueous phase further comprises a surfactant.

53. The antimicrobial composition according to claim 52, wherein the surfactant is a nonionic surfactant.

54. The antimicrobial composition according to claim 53, wherein the nonionic surfactant has an average HLB (hydrophilic-lipophilic balance) value of about 12 to about 15.

55. The antimicrobial composition according to claim 53 or claim 54, wherein the nonionic surfactant is selected from TRITON TM X-114 ((1,1,3,3-tetramethylbutyl)phenyl-polyethylene glycol), SILWET TM L-7604 (siloxane polyalkylene oxide copolymer) and combinations thereof.

56. The antimicrobial composition according to any one of claims 52 to 55, wherein the surfactant is present in the aqueous phase in an amount of about 0.05 wt% to about 2 wt% based on the dry weight of the oil phase.

57. The antimicrobial composition according to any one of claims 52 to 56, wherein the surfactant is present in the aqueous phase in an amount of about 0.1 wt% to about 1 wt% based on the dry weight of the oil phase.

58. The antimicrobial composition according to any one of claims 1 to 57, wherein the aqueous phase further comprises an antifoaming agent or defoaming agent.

59. The antimicrobial composition according to claim 58, wherein the defoamer is ST 2410 (a star polymer-based defoamer).

60. The antimicrobial composition according to any one of claims 1 to 56, wherein the random polymer or interpenetrating polymer network is produced by random polymerization / crosslinking of: the first adduct; the polyethyleneimine intermediate or the second adduct; when present, the polyol; if reactive, the water-soluble polymer; and when present, the third polyfunctional crosslinking agent.

61. The antimicrobial composition according to any one of claims 1 to 56, wherein the oil phase further comprises a third adduct of the first polyfunctional crosslinking agent and a second quaternary ammonium salt, wherein ​ R 1a 、R 2a and R 3a each independently represents methyl or ethyl; A 1 is a linking group selected from the group consisting of: -(C3-C 20 alkylene)-, -(C3-C 20 heteroalkylene)-, -(C6-C 10 arylene)-(C3-C 20 alkylene)-, -(CR m1 R n1 ) x42 -W 42 -(CR p1 R q1 ) y42 - and -(CR m1 R n1 ) x43 -W 43 -(CR p1 R q1 ) y43 -, where -(C3-C 20 heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; and -(C3-C 20 alkylene)- and -(C3-C 20 heteroalkylene)- are optionally substituted with 1 to 6 substituents independently selected from: -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl); Each R m1 、R n1 、R p1 and R q1 is independently selected from H and C1-C4 alkyl; W 42 selected from -C(O)-; -C(O)O-; -OC(O)-; -C(O)NH-; and -NHC(O)-; W 43 selected from 5- to 6-membered cycloalkyl, C6-C 10 aryl, 5- to 6-membered heteroalkyl and 5- to 6-membered heteroaryl, wherein the heteroalkyl contains 1-2 ring heteroatoms selected from O, N, S and Si; and the heteroaryl contains 1-3 ring heteroatoms selected from O, N, S and Si; x42 is an integer from 1 to 19, and y42 is an integer from 1 to 19, where 3 ≤ (x42 + y42) ≤ 20; x43 is an integer from 1 to 20, and y43 is an integer from 0 to 19, where 3 ≤ (x43 + y43) ≤ 20; Y 1 selected from the group consisting of: -OH, -NHR 4a , -SH, -CO2H, -C(O)NHR 4a , -C(S)NHR 4a , Each R 4a is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl), where -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si; and X - Independently an acetate ion, a halide ion, a sulfate ion, a sulfonate ion, a phosphate ion, a phosphonate ion, a carbonate ion, a silicate ion, a hexafluorophosphate ion, a hexafluoroantimonate ion, a trifluoromethanesulfonate ion, a borate ion, or an organic-substituted derivative of any of the foregoing.

62. The antimicrobial composition according to any one of claims 1 to 56, wherein the oil phase further comprises a fourth polyfunctional crosslinking agent and a third adduct of a second quaternary ammonium salt, wherein ​ R 1a 、R 2a and R 3a are each independently methyl or ethyl; A 1 is a linking group selected from the group consisting of: -(C3-C 20 alkylene)-, -(C3-C 20 heteroalkylene)-, -(C6-C 10 arylene)-(C3-C 20 alkylene)-, -(CR m1 R n1 ) x42 -W 42 -(CR p1 R q1 ) y42 - and -(CR m1 R n1 ) x43 -W 43 -(CR p1 R q1 ) y43 -, where -(C3-C 20 heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; and -(C3-C 20 alkylene)- and -(C3-C 20 heteroalkylene)- are optionally substituted with 1 to 6 substituents independently selected from: -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl); Each R m1 、R n1 、R p1 and R q1 is independently selected from H and C1-C4 alkyl; W 42 selected from -C(O)-; -C(O)O-; -OC(O)-; -C(O)NH-; and -NHC(O)-; W 43 selected from 5- to 6-membered cycloalkyl, C6-C 10 aryl, 5- to 6-membered heteroalkyl and 5- to 6-membered heteroaryl, wherein the heteroalkyl contains 1-2 ring heteroatoms selected from O, N, S and Si; and the heteroaryl contains 1-3 ring heteroatoms selected from O, N, S and Si; x42 is an integer from 1 to 19, and y42 is an integer from 1 to 19, where 3 ≤ (x42 + y42) ≤ 20; x43 is an integer from 1 to 20, and y43 is an integer from 0 to 19, where 3 ≤ (x43 + y43) ≤ 20; Y 1 selected from the group consisting of: -OH, -NHR 4a , -SH, -CO2H, -C(O)NHR 4a , -C(S)NHR 4a , Each R 4a is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl), where -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si; and X - Independently an acetate ion, a halide ion, a sulfate ion, a sulfonate ion, a phosphate ion, a phosphonate ion, a carbonate ion, a silicate ion, a hexafluorophosphate ion, a hexafluoroantimonate ion, a trifluoromethanesulfonate ion, a borate ion, or an organically substituted derivative of any of the foregoing.

63. The antimicrobial composition according to claim 62, wherein the fourth polyfunctional crosslinking agent is different from the first polyfunctional crosslinking agent, and different from the second polyfunctional crosslinking agent when present, and different from the third polyfunctional crosslinking agent when present.

64. The antimicrobial composition according to claim 62 or claim 63, wherein the fourth polyisocyanate is present in the oil phase in an amount of about 0.1 wt% to about 15 wt% based on the dry weight of the oil phase.

65. The antimicrobial composition according to any one of claims 62 to 64, wherein the fourth polyfunctional crosslinking agent is a fourth polyisocyanate.

66. The antimicrobial composition according to claim 65, wherein the average isocyanate functionality of the fourth polyisocyanate is 2 to 5.

67. The antimicrobial composition according to claim 65 or claim 66, wherein the fourth polyisocyanate is prepared from diisocyanates selected from the group consisting of: hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), trimethylhexamethylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

68. The antimicrobial composition according to claim 65 or claim 66, wherein the fourth polyisocyanate is selected from the group consisting of: N-3300, N-100, Z4470SN, T-series polyisocyanates and M-series polyisocyanates.

69. The antimicrobial composition according to any one of claims 61 to 68, wherein the second quaternary ammonium salt is (C2DMDEG-Br).

70. The antimicrobial composition according to any one of claims 61 to 69, wherein the second quaternary ammonium salt is present in the oil phase in an amount of about 1 wt% to about 15 wt% based on the dry weight of the oil phase.

71. The antimicrobial composition according to any one of claims 61 to 70, wherein the second quaternary ammonium salt is present in the oil phase in an amount of about 3 wt% to about 10 wt% based on the dry weight of the oil phase.

72. The antimicrobial composition according to any one of claims 61 to 71, wherein the average isocyanate functionality of the third adduct is 2 to 3.

73. The antimicrobial composition according to any one of claims 61 to 72, wherein the average isocyanate functionality of the third adduct is about 2.05 to about 2.

3.

74. The antimicrobial composition according to any one of claims 61 to 73, wherein the third adduct is present in the oil phase in an amount of about 2 wt% to about 30 wt% based on the dry weight of the oil phase.

75. The antimicrobial composition according to any one of claims 61 to 74, wherein the reactive isocyanate functional groups on the third adduct are protected with a blocking agent.

76. The antimicrobial composition according to claim 75, wherein the blocking agent is selected from the group consisting of: oximes, phenols, malonic esters, alcohols, lactams, dicarbonyl compounds, isohydroxamic acid esters, bisulfite addition compounds, hydroxylamines, esters of p-hydroxybenzoic acid, and salicylic acid.

77. The antimicrobial composition according to claim 76, wherein the blocking agent is selected from the group consisting of acetone oxime, methyl ethyl ketoxime, sodium bisulfite, diethyl malonate, and 3,5-dimethylpyrazole.

78. The antimicrobial composition according to any one of claims 61 to 74, wherein the random polymer or the interpenetrating polymer network is produced by random polymerization / crosslinking of: the first adduct; the polyethyleneimine intermediate or the second adduct; The third adduct; when present, the polyol; If reactive, the water-soluble polymer; and when present, the third polyfunctional crosslinking agent.

79. The antimicrobial composition according to any one of claims 1 to 59 or 61 to 77, wherein the oil phase further comprises a chain extender selected from the group consisting of: HO-(C n H 2n )-OH and HO-(C n H 2n-2 )-OH or a combination thereof, where n is an integer from 2 to 8.

80. The antimicrobial composition according to claim 79, wherein the chain extender is propylene glycol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexanedimethanol, or a combination of two or more thereof.

81. The antimicrobial composition according to claim 79 or 80, wherein the chain extender is present in the oil phase in an amount of up to about 10% by weight based on the dry weight of the oil phase.

82. The antimicrobial composition according to any one of claims 79 to 81, wherein the chain extender is present in the oil phase in an amount of about 0.5% to about 10% by weight based on the dry weight of the oil phase.

83. The antimicrobial composition according to any one of claims 79 to 82, wherein the random polymer or interpenetrating polymer network is produced by random polymerization / crosslinking of: the first adduct; the polyethyleneimine intermediate or the second adduct; when present, the third adduct; when present, the polyol; the chain extender; if reactive, the water-soluble polymer; and when present, the third polyfunctional crosslinking agent.

84. The antimicrobial composition according to any one of claims 1 to 83, wherein the polyethyleneimine intermediate is present in the oil phase in an amount of about 0.1% to about 50% by weight based on the dry weight of the oil phase.

85. The antimicrobial composition according to any one of claims 1 to 84, wherein the hydroxyalkylene functional group is optionally substituted with a C1-C6 alkyl group, and the C1-C6 alkyl group is optionally substituted with a substituent selected from the following: -N + (R 20 )3X - 、-(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl; each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted with: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl); and each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion, and borate ion, and organically substituted derivatives thereof.

86. The antimicrobial composition according to any one of claims 1 to 85, wherein the hydroxyalkylene functional group is hydroxyethylene, hydroxypropylene, hydroxybutylene, or an oligomer thereof.

87. The antimicrobial composition according to any one of claims 1 to 84, wherein the polyethyleneimine intermediate comprises a reaction product of reagents, the reagents comprising polyethyleneimine, a monoepoxide, and an alkylating agent, wherein the monoepoxide is optionally substituted with a C1-C6 alkyl group, and the C1-C6 alkyl group is optionally substituted with a substituent selected from: -(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with a hydroxyl group, C1-C6 alkoxy, C6-C 10 aryl optionally substituted with a C1-C6 alkyl group, and a carboxyl group.

88. The antimicrobial composition according to claim 87, wherein the monoepoxide is a C1-C6 alkyl epoxide.

89. The antimicrobial composition according to claim 88, wherein the C1-C6 alkyl epoxide is selected from the group consisting of propyl epoxide, butyl epoxide, and hexyl epoxide.

90. The antimicrobial composition according to any one of claims 1 to 84, wherein the polyethyleneimine intermediate comprises the reaction product of reagents, the reagents comprising polyethyleneimine, a monoepoxide and optionally an alkylating agent; the monoepoxide is substituted by -(C1-C6 alkyl)-N + (R 20 )3X - ; each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary substituted N; and C6-C 10 aryl optionally substituted by: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2 or -OC(O)-(C1-C6 alkyl); and each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and organically substituted derivatives thereof.

91. The antimicrobial composition according to any one of claims 87 to 90, wherein the alkylating agent comprises one or more R 21 -LG, wherein each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH; and each LG is a leaving group.

92. The antimicrobial composition according to claim 91, wherein the alkylating agent is benzyl halide or hexyl halide.

93. The antimicrobial composition according to any one of claims 1 to 84, wherein the polyethyleneimine intermediate comprises the reaction product of reagents comprising polyethyleneimine and haloalkanol.

94. The antimicrobial composition according to claim 93, wherein the haloalkanol is X 30 -(C2-C6 alkylene)-OH, wherein X 30 is Cl, Br or I.

95. The antimicrobial composition according to any one of claims 87 to 94, wherein the reagents of the reaction product comprised in the polyethyleneimine intermediate further comprise monoisocyanate.

96. The antimicrobial composition according to claim 95, wherein the monoisocyanate comprises one or more R 30 -NCO, wherein each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1-3 substituents independently selected from: halogen, -SiR a (OR b )(OR c ) and -(C6-C 10 aryl); and (2) C6-C 10 aryl optionally substituted with 1-3 substituents independently selected from: halogen, -(C1-C6 alkyl) and -SiR a (OR b )(OR c ); wherein each R a is independently C1-C6 alkyl; and each R b and each R c is independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3.

97. The antimicrobial composition according to claim 95 or claim 96, wherein the monoisocyanate comprises octyl isocyanate, octadecyl isocyanate, or a combination thereof.

98. The antimicrobial composition according to any one of claims 87 to 97, wherein the polyethyleneimine has a molecular weight of from about 300 Daltons to about 270,000 Daltons.

99. The antimicrobial composition according to any one of claims 87 to 98, wherein the polyethyleneimine has a molecular weight of from about 10,000 Daltons to about 200,000 Daltons.

100. The antimicrobial composition according to any one of claims 87 to 99, wherein the polyethyleneimine has a molecular weight of from about 25,000 Daltons to about 120,000 Daltons.

101. The antimicrobial composition according to any one of claims 87 to 100, wherein the polyethyleneimine is branched.

102. The antimicrobial composition according to any one of claims 87 to 100, wherein the polyethyleneimine is hyperbranched.

103. The antimicrobial composition according to any one of claims 87 to 102, wherein the ratio of primary amine:secondary amine:tertiary amine of the polyethyleneimine is from about 1:2:1 to about 1:1:

1.

104. The antimicrobial composition according to any one of claims 87 to 102, wherein the ratio of primary amine:secondary amine:tertiary amine of the polyethyleneimine is about 1:1:0.

7.

105. The antimicrobial composition according to any one of claims 1 to 84, wherein the polyethyleneimine intermediate is selected from a copolymer of two or more of them, wherein: Each Y 3 is independently H or -O-Y 2 where each Y 3 is not H; Each Y 2 is independently H or -C(O)-NHR 30 , where each Y 2 cannot be -C(O)-NHR 30 ; Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 is independently selected from hydrogen; C1-C6 alkyl optionally substituted with a substituent selected from: -N + (R 20 )3X - 、-(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl; and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tert-substituted N; and C6-C 10 aryl optionally substituted with: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl); Each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 is independently selected from (1) C6-C optionally substituted with 1-3 substituents independently selected from the following 20 alkyl: halogen, –SiR a (OR b )(OR c ) and -(C6-C 10 aryl); and (2) C6-C optionally substituted with 1-3 substituents independently selected from the following 10 aryl: halogen, -(C1-C6 alkyl) and -SiR a (OR b )(OR c ); wherein each R a is independently C1-C6 alkyl; and each R b and each R c is independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3; and Each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion, and borate ion, and their organically substituted derivatives; Provided that: When R 10 is a C1-C6 alkyl group optionally substituted with a substituent selected from the following, then the polyethyleneimine intermediate is selected from -(C6-C 10 aryl), and optionally -OH-substituted -(C1-C6 alkoxy), -(C1-C6 alkoxy), optionally -(C1-C6 alkyl)-substituted -(C6-C 10 aryl), and carboxyl group.

106. The antimicrobial composition according to any one of claims 1 to 84, wherein the polyethyleneimine intermediate is wherein each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000.

107. The antimicrobial composition according to any one of claims 1 to 106, wherein at least 20% of the nitrogen atoms in the polyethyleneimine intermediate are quaternized.

108. The antimicrobial composition according to any one of claims 1 to 84, wherein the second adduct has the formula (I): Wherein: Each A is independently selected from a copolymer of any two or more thereof; and the attachment of each A forms a urethane bond; Each Y 3 is independently H or -O-Y 2 where each Y 3 is not H; Each Y 2 is independently H or -C(O)-NHR 30 , where each Y 2 cannot be -C(O)-NHR 30 ; Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 is independently selected from hydrogen; C1-C6 alkyl optionally substituted with a substituent selected from: -N + (R 20 )3X - 、-(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl; and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted with: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl); Each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1-3 substituents independently selected from: halogen, –SiR a (OR b )(OR c ) and -(C6-C 10 aryl); (2) C6-C 10 aryl optionally substituted with 1-3 substituents independently selected from: halogen, -(C1-C6 alkyl) and –SiR a (OR b )(OR c ); and (3) wherein each R a is independently -(C1-C6 alkyl); and each R b and each R c is independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3; Each R 40 independently is optionally -(C1-C 10 alkylene)- substituted by phenyl or a 3- to 8-membered cycloalkyl ring; and Each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and their organically substituted derivatives; Provided that: When R 10 is a C1-C6 alkyl optionally substituted with a substituent selected from the following, then each A is independently selected from -(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl.

109. The antimicrobial composition according to any one of claims 1 to 84, wherein the second adduct has the formula (II): Wherein: Each A is independently selected from a copolymer of any two or more thereof; and the attachment of each A forms a urethane bond; Each Y 3 is independently H or -O-Y 2 , where each Y 3 is not H; Each Y 2 is independently H or –C(O)-NHR 30 , where each Y 2 cannot be -C(O)-NHR 30 ; Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 is independently selected from hydrogen; C1-C6 alkyl optionally substituted with a substituent selected from: -N + (R 20 )3X - , -(C6-C 10 aryl), and -(C1-C6 alkoxy), -(C1-C6 alkoxy) optionally substituted with -OH, -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl; and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted with: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl); Each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 is independently selected from (1) C6-C optionally substituted with 1-3 substituents independently selected from the following 20 alkyl: halogen, -SiR a (OR b )(OR c ) and -(C6-C 10 aryl); (2) C6-C optionally substituted with 1-3 substituents independently selected from the following 10 aryl: halogen, -(C1-C6 alkyl) and -SiR a (OR b )(OR c ); and (3) wherein each R a is independently -(C1-C6 alkyl); and each R b and each R c is independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3; Each R 40 independently is optionally -(C1-C 10 alkylene)- substituted by phenyl or a 3- to 8-membered cycloalkyl ring; and Each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and their organically substituted derivatives; Provided that: When R 10 is a C1-C6 alkyl optionally substituted with a substituent selected from the following, then each A is independently selected from -(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl.

110. A polymer or interpenetrating polymer network comprising a random polymerization / crosslinking product of reagents, said reagents comprising (i) a first polyfunctional crosslinking agent and a first adduct of a first quaternary ammonium salt; (ii) a polyol; (iii) a polyethyleneimine intermediate or a second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinking agent; And (iv) optionally a third polyfunctional crosslinking agent.

111. The polymer or interpenetrating polymer network according to claim 110, wherein the first quaternary ammonium salt has a chemical structure of, wherein R 1 selected from the group consisting of: -(C8-C 30 alkyl), -(C8-C 30 heteroalkyl), -(C8-C 30 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl), -(C6-C 10 aryl)-(C8-C 30 alkyl), -(C6-C 10 aryl)-(C8-C 30 heteroalkyl), -(CR m R n ), x10 -W 10 -(CR p R q ), y10 -H and -(CR m R n ), x11 -W 11 -(CR p R q ), y11 H-; wherein -(C8-C 30 heteroalkyl), -(C8-C 30 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl)-(C8-C 30 heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S and Si; R 2 selected from the group consisting of: -(C1-C4 alkyl), -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl), -(C6-C 10 aryl)-(C1-C4 alkyl), -(C6-C 10 aryl)-(C1-C4 heteroalkyl); -(CR m R n ) x20 -W 20 -(CR p R q ) y20 -H and -(CR m R n ) x21 -W 21 -(CR p R q ) y21 -H; wherein -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl)-(C1-C4 heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S and Si; R 3 selected from the group consisting of: -(C1-C 30 alkyl), -(C1-C 30 heteroalkyl), -(C1-C 30 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl), -(C6-C 10 aryl)-(C1-C 30 alkyl), -(C6-C 10 aryl)-(C1-C 30 heteroalkyl), -(CR m R n ) x30 -W 30 -(CR p R q ) y30 -H and -(CR m R n ) x31 -W 31 -(CR p R q ) y31 -H; wherein -(C1-C 30 heteroalkyl), -(C1-C 30 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl)-(C1-C 30 heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S and Si; A is a linking group selected from the group consisting of: -(C3-C 20 alkylene)-, -(C3-C 20 heteroalkylene)-, -(C6-C 10 arylene)-(C3-C 20 alkylene)-, -(CR m R n ) x40 -W 40 -(CR p R q ) y40 - and -(CR m R n ) x41 -W 41 -(CR p R q ) y41 -, where -(C3-C 20 heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; and -(C3-C 20 alkylene)- and -(C3-C 20 heteroalkylene)- are optionally substituted with 1 to 6 substituents independently selected from the following: -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl); Each R m , R n , R p and R q is independently selected from H and C1-C4 alkyl; W 10 , W 20 , W 30 and W 40 independently selected from -C(O)-; -C(O)O-; -OC(O)-; -C(O)NH-; and -NHC(O)-; W 11 、W 21 、W 31 and W 41 are independently selected from 5- to 6-membered cycloalkyl, C6-C 10 aryl, 5- to 6-membered heterocycloalkyl and 5- to 6-membered heteroaryl, wherein the heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S and Si; and the heteroaryl contains 1-3 ring heteroatoms selected from O, N, S and Si; x10 is an integer from 1 to 30, and y10 is an integer from 0 to 29, where 8 ≤ (x10 + y10) ≤ 30; x11 is an integer from 1 to 30, and y11 is an integer from 0 to 29, where 8 ≤ (x11 + y11) ≤ 30; x20 is an integer from 1 to 4, and y20 is an integer from 0 to 3, where x20 + y20 ≤ 4; x21 is an integer from 1 to 4, and y21 is an integer from 0 to 3, where x21 + y21 ≤ 4; x30 is an integer from 1 to 30, and y30 is an integer from 0 to 29, where x30 + y30 ≤ 30; x31 is an integer from 1 to 30, and y31 is an integer from 0 to 29, where x31 + y31 ≤ 30; x40 is an integer from 1 to 19, and y40 is an integer from 1 to 19, where 3 ≤ (x40 + y40) ≤ 20; x41 is an integer from 1 to 20, and y41 is an integer from 0 to 19, where 3 ≤ (x41 + y41) ≤ 20; Y is selected from the group consisting of: -OH, -NHR 4 , -SH, -CO2H, -C(O)NHR 4 , -C(S)NHR 4 , Each R 4 is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl), where -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si; and X - Independently an acetate ion, a halide ion, a sulfate ion, a sulfonate ion, a phosphate ion, a phosphonate ion, a carbonate ion, a silicate ion, a hexafluorophosphate ion, a hexafluoroantimonate ion, a trifluoromethanesulfonate ion, a borate ion or an organic-substituted derivative of any of the foregoing.

112. The polymer or interpenetrating polymer network according to claim 111, wherein R 1 is selected from the group consisting of: -(C 12 -C 30 alkyl), -(C 12 -C 30 heteroalkyl), -(C 12 -C 30 alkyl)-(C6-C 10 aryl), -(C 12 -C 30 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl)-(C 12 -C 30 alkyl) and -(C6-C 10 aryl)-(C 12 -C 30 heteroalkyl); wherein -(C 12 -C 30 heteroalkyl), -(C 12 -C 30 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl)-(C 12 -C 30 heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S, and Si.

113. The polymer or interpenetrating polymer network according to claim 111 or claim 112, wherein R 3 is selected from the group consisting of: -(C1-C4 alkyl), -(C1-C4 heteroalkyl), -(C1-C4 alkyl)-(C6-C 10 aryl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl)-(C1-C4 alkyl) and -(C6-C 10 aryl)-(C1-C4 heteroalkyl); wherein -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl)-(C1-C4 heteroalkyl) each have 1 to 4 heteroatoms independently selected from O, S and Si.

114. The polymer or interpenetrating polymer network according to any one of claims 111 to 113, wherein R 2 and R 3 are methyl groups.

115. The polymer or interpenetrating polymer network according to any one of claims 111 to 114, wherein A is -(CH2) m - or -(CH2CHR 5 -O-) n CH2CHR 5 -, where m is an integer from 2 to 20; n is 0, 1, 2, 3, 4 or 5; and each R 5 is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl) and -(C6-C 10 aryl), wherein -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S and Si.

116. The polymer or interpenetrating polymer network according to claim 115, wherein R 5 is H or methyl.

117. The polymer or interpenetrating polymer network according to any one of claims 110 to 116, wherein the first quaternary ammonium salt is or a combination of two or more of them.

118. The polymer or interpenetrating polymer network according to any one of claims 110 to 117, wherein the first quaternary ammonium salt is present in the dry polymer or interpenetrating polymer network in an amount of about 1 wt.% to about 50 wt.%.

119. The polymer or interpenetrating polymer network according to any one of claims 110 to 118, wherein the first polyfunctional crosslinking agent is a first polyisocyanate; the second polyfunctional crosslinking agent, when present, is a second polyisocyanate; the third polyfunctional crosslinking agent, when present, is a third polyisocyanate; and the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate are different.

120. The polymer or interpenetrating polymer network according to any one of claims 110 to 118, wherein the first polyfunctional crosslinking agent is a first polyisocyanate; the second polyfunctional crosslinking agent, when present, is a second polyisocyanate; the third polyfunctional crosslinking agent, when present, is a third polyisocyanate; and the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate are the same.

121. The polymer or interpenetrating polymer network according to claim 119 or claim 120, wherein the average isocyanate functionality of each of the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate is from 2 to 5.

122. The polymer or interpenetrating polymer network according to claim 121, wherein the average isocyanate functionality of each of the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate is from 3 to 4.

123. The polymer or interpenetrating polymer network according to any one of claims 119 to 122, wherein each of the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate is prepared from a diisocyanate independently selected from the group consisting of: hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), trimethylhexamethylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

124. The polymer or interpenetrating polymer network according to any one of claims 119 to 122, wherein each of the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate is independently selected from the group consisting of: N-3300, N-100, Z4470SN, T-series polyisocyanates and M-series polyisocyanates.

125. The polymer or interpenetrating polymer network according to any one of claims 110 to 124, wherein the first polyfunctional crosslinking agent is present in the dry polymer or interpenetrating polymer network in an amount of from about 2 wt.% to about 25 wt.%.

126. The polymer or interpenetrating polymer network according to any one of claims 110 to 125, wherein the second polyfunctional crosslinking agent is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1 wt.% to about 10 wt.%.

127. The polymer or interpenetrating polymer network according to any one of claims 110 to 126, wherein the third polyfunctional crosslinking agent is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1 wt.% to about 20 wt.%.

128. The polymer or interpenetrating polymer network according to any one of claims 110 to 127, wherein the average isocyanate functionality of the first adduct is from 2 to 3.

129. The polymer or interpenetrating polymer network according to claim 128, wherein the average isocyanate functionality of the first adduct is from about 2.05 to about 2.

3.

130. The polymer or interpenetrating polymer network according to any one of claims 110 to 129, wherein the polyol is selected from the group consisting of: polyether polyols, polyester polyols, polyacrylate polyols, polymethacrylate polyols, polycaprolactone polyols, polybutadiene polyols, poly(acrylonitrile-co-butadiene) polyols, polysiloxane polyols, copolymers of any two or more thereof, and combinations of any two or more thereof.

131. The polymer or interpenetrating polymer network according to claim 130, wherein the polyol is selected from the group consisting of: poly(tetramethylene glycol), polyethylene glycol, polypropylene glycol, poly(ethylene glycol-b-propylene glycol-b-ethylene glycol), and poly(propylene glycol-b-polyethylene glycol-b-propylene glycol).

132. The polymer or interpenetrating polymer network according to claim 130 or claim 131, wherein the weight average molecular weight of the polyol is from about 300 to about 3000.

133. The polymer or interpenetrating polymer network according to any one of claims 130 to 132, wherein the weight average molecular weight of the polyol is from about 400 to about 2000.

134. The polymer or interpenetrating polymer network according to any one of claims 130 to 123, wherein the weight average molecular weight of the polyol is from about 600 to about 1500.

135. The polymer or interpenetrating polymer network according to any one of claims 130 to 134, wherein the polyol is present in the dry polymer or interpenetrating polymer network in an amount of from about 1 wt.% to about 40 wt.%.

136. The polymer or interpenetrating polymer network according to any one of claims 110 to 135, wherein the reagent further comprises a third adduct of the first polyfunctional crosslinking agent and a second quaternary ammonium salt, wherein ​ R 1a 、R 2a and R 3a each independently represents methyl or ethyl; A 1 is a linking group selected from the group consisting of: -(C3-C 20 alkylene)-, -(C3-C 20 heteroalkylene)-, -(C6-C 10 arylene)-(C3-C 20 alkylene)-, -(CR m1 R n1 ) x42 -W 42 -(CR p1 R q1 ) y42 - and -(CR m1 R n1 ) x43 -W 43 -(CR p1 R q1 ) y43 -, where -(C3-C 20 heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; and -(C3-C 20 alkylene)- and -(C3-C 20 heteroalkylene)- are optionally substituted with 1 to 6 substituents independently selected from the following: -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl); Each R m1 、R n1 、R p1 and R q1 is independently selected from H and C1-C4 alkyl; W 42 selected from -C(O)-; -C(O)O-; -OC(O)-; -C(O)NH-; and -NHC(O)-; W 43 selected from 5- to 6-membered cycloalkyl, C6-C 10 aryl, 5- to 6-membered heteroalkyl and 5- to 6-membered heteroaryl, wherein the heteroalkyl contains 1-2 ring heteroatoms selected from O, N, S and Si; and the heteroaryl contains 1-3 ring heteroatoms selected from O, N, S and Si; x42 is an integer from 1 to 19, and y42 is an integer from 1 to 19, where 3 ≤ (x42 + y42) ≤ 20; x43 is an integer from 1 to 20, and y43 is an integer from 0 to 19, where 3 ≤ (x43 + y43) ≤ 20; Y 1 selected from the group consisting of: -OH, -NHR 4a , -SH, -CO2H, -C(O)NHR 4a , -C(S)NHR 4a , Each R 4a is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl), where -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si; and X - Independently an acetate ion, a halide ion, a sulfate ion, a sulfonate ion, a phosphate ion, a phosphonate ion, a carbonate ion, a silicate ion, a hexafluorophosphate ion, a hexafluoroantimonate ion, a trifluoromethanesulfonate ion, a borate ion, or an organic-substituted derivative of any of the foregoing.

137. A polymer or interpenetrating polymer network according to any one of claims 110 to 135, wherein the reagent further comprises a fourth polyfunctional crosslinking agent and a third adduct of a second quaternary ammonium salt, wherein ​ R 1a 、R 2a and R 3a are each independently methyl or ethyl; A 1 is a linking group selected from the group consisting of: -(C3-C 20 alkylene)-, -(C3-C 20 heteroalkylene)-, -(C6-C 10 arylene)-(C3-C 20 alkylene)-, -(CR m1 R n1 ) x42 -W 42 -(CR p1 R q1 ) y42 - and -(CR m1 R n1 ) x43 -W 43 -(CR p1 R q1 ) y43 -, where -(C3-C 20 heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; and -(C3-C 20 alkylene)- and -(C3-C 20 heteroalkylene)- are optionally substituted with 1 to 6 substituents independently selected from the following: -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl); Each R m1 、R n1 、R p1 and R q1 is independently selected from H and C1-C4 alkyl; W 42 selected from -C(O)-; -C(O)O-; -OC(O)-; -C(O)NH-; and -NHC(O)-; W 43 selected from 5- to 6-membered cycloalkyl, C6-C 10 aryl, 5- to 6-membered heteroalkyl and 5- to 6-membered heteroaryl, wherein the heteroalkyl contains 1-2 ring heteroatoms selected from O, N, S and Si; and the heteroaryl contains 1-3 ring heteroatoms selected from O, N, S and Si; x42 is an integer from 1 to 19, and y42 is an integer from 1 to 19, where 3 ≤ (x42 + y42) ≤ 20; x43 is an integer from 1 to 20, and y43 is an integer from 0 to 19, where 3 ≤ (x43 + y43) ≤ 20; Y 1 selected from the group consisting of: -OH, -NHR 4a , -SH, -CO2H, -C(O)NHR 4a , -C(S)NHR 4a , Each R 4a is independently selected from the group consisting of: H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl), where -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si; and X - Independently an acetate ion, a halide ion, a sulfate ion, a sulfonate ion, a phosphate ion, a phosphonate ion, a carbonate ion, a silicate ion, a hexafluorophosphate ion, a hexafluoroantimonate ion, a trifluoromethanesulfonate ion, a borate ion, or an organic-substituted derivative of any of the foregoing.

138. The polymer or interpenetrating polymer network according to claim 137, wherein the fourth polyfunctional crosslinking agent is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1 wt.% to about 15 wt.%.

139. The polymer or interpenetrating polymer network according to claim 137 or claim 138, wherein the fourth polyfunctional crosslinking agent is different from the first polyfunctional crosslinking agent, and different from the second polyfunctional crosslinking agent when present, and different from the third polyfunctional crosslinking agent when present.

140. The polymer or interpenetrating polymer network according to any one of claims 137 to 139, wherein the fourth polyfunctional crosslinking agent is a fourth polyisocyanate.

141. The polymer or interpenetrating polymer network according to claim 140, wherein the fourth polyisocyanate is prepared from a diisocyanate selected from the group consisting of: hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), trimethylhexamethylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

142. The polymer or interpenetrating polymer network according to claim 140, wherein the fourth polyisocyanate is selected from the group consisting of: N-3300, N-100, Z4470SN, T series polyisocyanates and M series polyisocyanates.

143. The polymer or interpenetrating polymer network according to any one of claims 136 to 142, wherein the second quaternary ammonium salt is (C2DMDEG-Br).

144. The polymer or interpenetrating polymer network according to any one of claims 136 to 143, wherein the second quaternary ammonium salt is present in the dry polymer or interpenetrating polymer network in an amount of from about 1 wt.% to about 15 wt.%.

145. The polymer or interpenetrating polymer network according to any one of claims 136 to 144, wherein the average isocyanate functionality of the third adduct is from 2 to 3.

146. The polymer or interpenetrating polymer network according to any one of claims 136 to 145, wherein the average isocyanate functionality of the third adduct is from about 2.05 to about 2.

3.

147. The polymer or interpenetrating polymer network according to any one of claims 136 to 146, wherein the third adduct is present in the dry polymer or interpenetrating polymer network in an amount of from about 2 wt.% to about 30 wt.%.

148. The polymer or interpenetrating polymer network according to any one of claims 110 to 147, wherein the polyethyleneimine intermediate is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1 wt.% to about 50 wt.%.

149. The polymer or interpenetrating polymer network according to any one of claims 110 to 148, wherein the polyethyleneimine intermediate comprises an optionally substituted hydroxyalkylene functional group, and the optionally substituted hydroxyalkylene functional group reacts with the first adduct and, if present, the second polyfunctional crosslinking agent.

150. The polymer or interpenetrating polymer network according to claim 149, wherein the hydroxyalkylene functional group is optionally substituted with a C1-C6 alkyl group, and the C1-C6 alkyl group is optionally substituted with a substituent selected from the following: -N + (R 20 )3X - , -(C6-C 10 aryl), and -(C1-C6 alkoxy), -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl; each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted with: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl); and each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion, and borate ion, and organically substituted derivatives thereof.

151. The polymer or interpenetrating polymer network according to claim 149 or claim 150, wherein the hydroxyalkylene functional group is hydroxyethylene, hydroxypropylene, hydroxybutylene or an oligomer thereof.

152. The polymer or interpenetrating polymer network according to any one of claims 110 to 149, wherein the polyethyleneimine intermediate comprises the reaction product of reagents, the reagents comprising polyethyleneimine, a monoepoxide, and an alkylating agent, wherein the monoepoxide is optionally substituted with a C1-C6 alkyl group, and the C1-C6 alkyl group is optionally substituted with substituents selected from: -(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with a hydroxyl group, C1-C6 alkoxy, C6-C 10 aryl optionally substituted with a C1-C6 alkyl group, and carboxyl.

153. The polymer or interpenetrating polymer network according to claim 152, wherein the monoepoxide is a C1-C6 alkyl epoxide.

154. The polymer or interpenetrating polymer network according to claim 153, wherein the C1-C6 alkyl epoxide is selected from the group consisting of propyl epoxide, butyl epoxide and hexyl epoxide.

155. The polymer or interpenetrating polymer network according to any one of claims 110 to 149, wherein the polyethyleneimine intermediate comprises the reaction product of reagents, the reagents comprising polyethyleneimine, a monocyclic epoxide and optionally an alkylating agent; the monocyclic epoxide is substituted by -(C1-C6 alkyl)-N + (R 20 )3X - ; each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary substituted N; and C6-C 10 aryl optionally substituted by: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2 or -OC(O)-(C1-C6 alkyl); and each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and organically substituted derivatives thereof.

156. The polymer or interpenetrating polymer network according to any one of claims 152 to 155, wherein the alkylating agent comprises one or more R 21 -LG, wherein each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH; and each LG is a leaving group.

157. The polymer or interpenetrating polymer network according to claim 156, wherein the alkylating agent is benzyl halide or hexyl halide.

158. The polymer or interpenetrating polymer network according to any one of claims 110 to 149, wherein the polyethyleneimine intermediate comprises a reaction product of reagents comprising polyethyleneimine and haloalkanol.

159. The polymer or interpenetrating polymer network according to claim 158, wherein the haloalkanol is X 30 -(C2-C6 alkylene)-OH, wherein X 30 is Cl, Br or I.

160. The polymer or interpenetrating polymer network according to any one of claims 152 to 159, wherein the reagents of the reaction product comprised in the polyethyleneimine intermediate further comprise monoisocyanate.

161. The polymer or interpenetrating polymer network according to claim 160, wherein the mono-isocyanate comprises one or more R 30 -NCO, wherein each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1-3 substituents independently selected from: halogen, -SiR a (OR b )(OR c ) and -(C6-C 10 aryl); and (2) C6-C 10 aryl optionally substituted with 1-3 substituents independently selected from: halogen, -(C1-C6 alkyl) and -SiR a (OR b )(OR c ); wherein each R a is independently C1-C6 alkyl; and each R b and each R c is independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3.

162. The polymer or interpenetrating polymer network according to claim 160 or claim 161, wherein the monoisocyanate comprises octyl isocyanate, octadecyl isocyanate or a combination thereof.

163. The polymer or interpenetrating polymer network according to any one of claims 152 to 162, wherein the molecular weight of the polyethyleneimine is from about 300 Daltons to about 270,000 Daltons.

164. The polymer or interpenetrating polymer network according to any one of claims 152 to 163, wherein the molecular weight of the polyethyleneimine is from about 10,000 Daltons to about 200,000 Daltons.

165. The polymer or interpenetrating polymer network according to any one of claims 152 to 164, wherein the molecular weight of the polyethyleneimine is from about 25,000 Daltons to about 120,000 Daltons.

166. The polymer or interpenetrating polymer network according to any one of claims 152 to 165, wherein the polyethyleneimine is branched.

167. The polymer or interpenetrating polymer network according to any one of claims 152 to 165, wherein the polyethyleneimine is hyperbranched.

168. The polymer or interpenetrating polymer network according to any one of claims 152 to 167, wherein the ratio of primary amine:secondary amine:tertiary amine of the polyethyleneimine is from about 1:2:1 to about 1:1:

1.

169. The polymer or interpenetrating polymer network according to any one of claims 152 to 167, wherein the ratio of primary amine:secondary amine:tertiary amine of the polyethyleneimine is about 1:1:0.

7.

170. The polymer or interpenetrating polymer network according to any one of claims 110 to 149, wherein the polyethyleneimine intermediate is selected from a copolymer of two or more of them, wherein: Each Y 3 is independently H or -O-Y 2 where each Y 3 is not H; Each Y 2 is independently H or –C(O)-NHR 30 , where each Y 2 cannot be -C(O)-NHR 30 ; Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 is independently selected from hydrogen; C1-C6 alkyl optionally substituted with a substituent selected from the following: -N(R 20 )3, (C6-C 10 aryl), and -(C1-C6 alkoxy), -(C1-C6 alkoxy) optionally substituted with -OH, -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl; and each R 20 is independently selected from the group consisting of C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted with the following: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl); Each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 is independently selected from (1) C6-C optionally substituted with 1-3 substituents independently selected from the following 20 alkyl: halogen, –SiR a (OR b )(OR c ) and -(C6-C 10 aryl); and (2) C6-C optionally substituted with 1-3 substituents independently selected from the following 10 aryl: halogen, -(C1-C6 alkyl) and -SiR a (OR b )(OR c ); wherein each R a is independently C1-C6 alkyl; and each R b and each R c is independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3; and Each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and their organically substituted derivatives; Provided that: When R 10 is a C1-C6 alkyl group optionally substituted with a substituent selected from the following, then the polyethyleneimine intermediate is selected from -(C6-C 10 aryl), and optionally -OH-substituted -(C1-C6 alkoxy), -(C1-C6 alkoxy), optionally -(C1-C6 alkyl)-substituted -(C6-C 10 aryl), and carboxyl.

171. The polymer or interpenetrating polymer network according to any one of claims 110 to 149, wherein the polyethyleneimine intermediate is where each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000.

172. The polymer or interpenetrating polymer network according to any one of claims 110 to 149, wherein the second adduct has the formula (I): Wherein: Each A is independently selected from a copolymer of any two or more thereof; and the attachment of each A forms a urethane bond; Each Y 3 is independently H or -O-Y 2 , where each Y 3 cannot be H; Each Y 2 is independently H or –C(O)-NHR 30 , where each Y 2 is not –C(O)-NHR 30 ; Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 is independently selected from hydrogen; C1-C6 alkyl optionally substituted with substituents selected from: -N(R 20 )3, (C6-C 10 aryl), and -(C1-C6 alkoxy), -(C1-C6 alkoxy) optionally substituted with -OH, -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl; and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted with: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl); Each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 is independently selected from (1) C6-C optionally substituted with 1-3 substituents independently selected from the following 20 alkyl: halogen, –SiR a (OR b )(OR c ) and -(C6-C 10 aryl); (2) C6-C optionally substituted with 1-3 substituents independently selected from the following 10 aryl: halogen, -(C1-C6 alkyl) and –SiR a (OR b )(OR c ); and (3) wherein each R a is independently -(C1-C6 alkyl); and each R b and each R c is independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3; Each R 40 is independently —(C1-C 10 alkylene)- optionally substituted by phenyl or a 3- to 8-membered cycloalkyl ring; and Each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion, and borate ion, and their organically substituted derivatives; Provided that: When R 10 is a C1-C6 alkyl optionally substituted with a substituent selected from the following, then each A is independently selected from -(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl.

173. The polymer or interpenetrating polymer network according to any one of claims 110 to 149, wherein the second adduct has the formula (II): Wherein: Each A is independently selected from or a copolymer of any two or more thereof; and the attachment of each A forms a urethane bond; Each Y 3 is independently H or -O-Y 2 , where each Y 3 cannot be H; Each Y 2 is independently H or –C(O)-NHR 30 wherein each Y 2 cannot be -C(O)-NHR 30 ; Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 is independently selected from hydrogen; C1-C6 alkyl optionally substituted with substituents selected from the following: -N(R 20 )3, (C6-C 10 aryl), and -(C1-C6 alkoxy), -(C1-C6 alkoxy) optionally substituted with -OH, -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl; and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted with: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl); Each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 is independently selected from (1) C6-C optionally substituted with 1-3 substituents independently selected from the following 20 alkyl: halogen, –SiR a (OR b )(OR c ) and -(C6-C 10 aryl); (2) C6-C optionally substituted with 1-3 substituents independently selected from the following 10 aryl: halogen, -(C1-C6 alkyl) and –SiR a (OR b )(OR c ); and (3) wherein each R a is independently -(C1-C6 alkyl); and each R b and each R c is independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3; Each R 40 independently is optionally -(C1-C 10 alkylene)- substituted by phenyl or a 3- to 8-membered cycloalkyl ring; and Each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and their organically substituted derivatives; Provided that: When R 10 is a C1-C6 alkyl optionally substituted with a substituent selected from the following, then each A is independently selected from -(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C6-C 10 aryl) optionally substituted with -(C1-C6 alkyl), and carboxyl.

174. The polymer or interpenetrating polymer network according to any one of claims 110 to 173, wherein the second adduct is present in the dry polymer or interpenetrating polymer network in an amount of about 1 wt.% to about 30 wt.%.

175. The polymer or interpenetrating polymer network according to any one of claims 110 to 174, wherein the reagent for the random polymerization / crosslinked product contained in the polymer or interpenetrating polymer network further comprises a water-soluble polymer.

176. The polymer or interpenetrating polymer network according to claim 175, wherein the water-soluble polymer is crosslinked with: (a) the first polyfunctional crosslinking agent incorporated in the first adduct; (b) when present, the second polyfunctional crosslinking agent incorporated in the second adduct; (c) when present, the third polyfunctional crosslinking agent; or (d) any combination of two or more of them.

177. The polymer or interpenetrating polymer network according to claim 175 or claim 176, wherein the water-soluble polymer is present in the dry polymer or interpenetrating polymer network in an amount of about 0.5 wt.% to about 15 wt.%.

178. The polymer or interpenetrating polymer network according to any one of claims 175 to 178, wherein the water-soluble polymer is selected from the group consisting of hydroxyethyl cellulose (HEC), hydroxypropyl cellulose, polyvinyl alcohol, poly(hydroxyethyl methacrylate-co-alkyl methacrylate), poly(hydroxyethyl methacrylate-co-alkyl acrylate), poly(acryloxyethyl methacrylate-co-alkyl methacrylate), poly(acryloxyethyl methacrylate-co-alkyl acrylate), polyacrylamide, polyethyleneimine intermediate, copolymers of two or more of them, copolymers of one or more of them with polyvinylpyrrolidone poly(glycidyl acrylate) or with poly(glycidyl methacrylate), and combinations or blends of two or more of them.

179. The polymer or interpenetrating polymer network according to any one of claims 175 to 178, wherein the water-soluble polymer is hydroxyethyl cellulose or a hydrophobically modified derivative thereof.

180. The polymer or interpenetrating polymer network according to any one of claims 175 to 178, wherein the water-soluble polymer is another polyethyleneimine intermediate.

181. The polymer or interpenetrating polymer network according to any one of claims 110 to 180, wherein the reagent for the random polymerization / crosslinked product comprised in the polymer or interpenetrating polymer network further comprises a chain extender selected from the group consisting of: HO-(C n H 2n )-OH and HO-(C n H 2n-2 )-OH, or a combination thereof, wherein n is an integer from 2 to 8.

182. The polymer or interpenetrating polymer network according to claim 181, wherein the chain extender is propylene glycol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexanedimethanol, or a combination of two or more thereof.

183. The polymer or interpenetrating polymer network according to claim 181 or claim 182, wherein the chain extender is present in the dry polymer or interpenetrating polymer network in an amount of about 0.5 wt.% to about 10 wt.%.

184. A composition comprising the polymer or interpenetrating polymer network according to any one of claims 110 to 184.

185. An antimicrobial compound selected from: a copolymer of two or more of them, wherein: Each Y 3 is independently H or -O-Y 2 , where each Y 3 is not H; Each Y 2 is independently H or -C(O)-NHR 30 wherein each Y 2 cannot be -C(O)-NHR 30 ; Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 is -N + (R 20 )3X - substituted C1-C6 alkyl, and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted with: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl); Each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 is independently selected from (1) C6-C optionally substituted with 1-3 substituents independently selected from the following 20 alkyl: halogen, -SiR a (OR b )(OR c ) and -(C6-C 10 aryl); and (2) C6-C optionally substituted with 1-3 substituents independently selected from the following 10 aryl: halogen, -(C1-C6 alkyl) and -SiR a (OR b )(OR c ); wherein each R a is independently C1-C6 alkyl; and each R b and each R c is independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3; and Each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion, and borate ion, and their organically substituted derivatives.

186. The antimicrobial compound according to claim 185, wherein each Y 2 is H.

187. The antimicrobial compound according to claim 185 or claim 186, wherein the compound is Each n is independently an integer selected from 1 to 3000, preferably an integer independently selected from 10 to 1000.

188. A random polymerization product of a polyethyleneimine intermediate and a crosslinking agent, wherein the polyethyleneimine intermediate is selected from: a copolymer of two or more of them, wherein: Each Y 3 is independently H or -O-Y 2 , where each Y 3 is not H; Each Y 2 is independently H or -C(O)-NHR 30 , where each Y 2 cannot be -C(O)-NHR 30 ; Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 is -N + (R 20 )3X - substituted C1-C6 alkyl, and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted with: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl); Each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1-3 substituents independently selected from: halogen, -SiR a (OR b )(OR c ) and -(C6-C 10 aryl); and (2) C6-C 10 aryl optionally substituted with 1-3 substituents independently selected from: halogen, -(C1-C6 alkyl) and -SiR a (OR b )(OR c ); wherein each R a is independently C1-C6 alkyl; and each R b and each R c is independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3; and Each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and their organically substituted derivatives.

189. The random polymerization product according to claim 188, wherein the crosslinking agent is a polyisocyanate.

190. The random polymerization product according to claim 189, wherein the polyisocyanate is prepared from a diisocyanate independently selected from the group consisting of: hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), m-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

191. The random polymerization product according to claim 189, wherein the polyisocyanate is independently selected from the group consisting of: N-3300, N-100, Z4470SN, T series polyisocyanates and M series polyisocyanates.

192. The random polymerization product according to any one of claims 188 to 191, wherein the random polymerization product has the formula (I): Wherein: Each A is independently selected from or a copolymer of any two or more thereof; and the attachment of each A forms a urethane bond; Each Y 3 is independently H or -O-Y 2 , where each Y 3 cannot be H; Each Y 2 is independently H or –C(O)-NHR 30 wherein each Y 2 cannot be -C(O)-NHR 30 ; Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 is -N + (R 20 )3X - substituted C1-C6 alkyl, and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted with: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl); Each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1-3 substituents independently selected from: halogen, -SiR a (OR b )(OR c ) and -(C6-C 10 aryl); (2) C6-C 10 aryl optionally substituted with 1-3 substituents independently selected from: halogen, -(C1-C6 alkyl) and -SiR a (OR b )(OR c ); and (3) wherein each R a is independently -(C1-C6 alkyl); and each R b and each R c is independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3; Each R 40 is independently —(C1-C 10 alkylene)- optionally substituted by phenyl or a 3- to 8-membered cycloalkyl ring; and Each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion, and borate ion, and their organically substituted derivatives.

193. The random polymerization product according to any one of claims 188 to 191, wherein the random polymerization product has the formula (II): Wherein: Each A is independently selected from a copolymer of any two or more thereof; and the attachment of each A forms a urethane bond; Each Y 3 is independently H or -O-Y 2 , where each Y 3 is not H; Each Y 2 is independently H or –C(O)-NHR 30 wherein each Y 2 cannot be -C(O)-NHR 30 ; Each n is independently an integer selected from 1 to 3000, preferably independently an integer selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 is -N + (R 20 )3X - substituted C1-C6 alkyl, and each R 20 is independently selected from the group consisting of: C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary-substituted N; and C6-C 10 aryl optionally substituted with: -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl); Each R 21 is independently selected from C1-C6 alkyl optionally substituted with substituents selected from: -OH, -(C1-C6 alkoxy), carboxyl, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl) and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 is independently selected from (1) C6-C 20 alkyl optionally substituted with 1-3 substituents independently selected from: halogen, –SiR a (OR b )(OR c ) and -(C6-C 10 aryl); (2) C6-C 10 aryl optionally substituted with 1-3 substituents independently selected from: halogen, -(C1-C6 alkyl) and –SiR a (OR b )(OR c ); and (3) wherein each R a is independently -(C1-C6 alkyl); and each R b and each R c is independently selected from -(C1-C6 alkyl) and –Si(C1-C6 alkyl)3; Each R 40 is independently —(C1-C 10 alkylene)- optionally substituted by phenyl or a 3- to 8-membered cycloalkyl ring; and Each X - is independently selected from the group consisting of acetate ion, halide ion, sulfate ion, sulfonate ion, phosphate ion, phosphonate ion, carbonate ion, silicate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion and borate ion, and their organically substituted derivatives.

194. A composition comprising an antimicrobial compound according to any one of claims 185 to 187.

195. A composition comprising a random polymerization product according to any one of claims 188 to 193.

196. An antimicrobial coating, coating fluid or spraying fluid comprising a composition according to any one of claims 1 to 109, 185 to 187 or 188 to 193.

197. A device, equipment, apparatus or fitting comprising a coating, coating fluid or spraying fluid according to claim 196.

198. The device, equipment, apparatus or fitting according to claim 197, wherein the coating fluid or the spraying fluid is water-soluble or water-dispersible.

199. The device, equipment, apparatus or fitting according to claim 197 or claim 198, wherein the device, equipment, apparatus or fitting is selected from the group consisting of: filters, air purifiers and face masks.

200. The device, equipment, apparatus or fitting according to claim 197 or claim 198, wherein the device, equipment, apparatus or fitting is selected from the group consisting of: keyboards, keypads, styli, mice, handheld devices, remote controllers, touchscreens, telephones, handheld devices and displays.

201. A personal care aid comprising a coating, coating fluid or spraying fluid according to claim 196.

202. The personal care aid according to claim 201, wherein the coating fluid or the spraying fluid is water-soluble or water-dispersible.

203. A method for disinfecting a surface, the method comprising applying a composition according to any one of claims 1 to 109, 185 to 187 or 188 to 193.

204. A method for reducing antimicrobial growth on a surface, the method comprising applying a composition according to any one of claims 1 to 109, 185 to 187 or 188 to 193 to the surface.

205. A method for preventing antimicrobial growth on a surface, the method comprising applying a composition according to any one of claims 1 to 109, 185 to 187 or 188 to 193 to the surface.

206. The method according to any one of claims 203 to 205, further comprising forming a coating solution containing the composition.

207. The method according to claim 206, further comprising directing the coating solution to a surface and providing a coating on the surface by applying the coating solution to the surface.

208. A polymer or interpenetrating polymer network prepared by: (a) reacting a first polyfunctional crosslinking agent with a first quaternary ammonium salt to form a first adduct; (b) optionally reacting a polyethyleneimine intermediate with a second polyfunctional crosslinking agent to form a second adduct; (c) optionally reacting the first polyfunctional crosslinking agent or a fourth polyfunctional crosslinking agent with a second quaternary ammonium salt to form a third adduct; (d) Combine (i) the first adduct, (ii) the polyethyleneimine intermediate or the second adduct, and (iii) when present, the third adduct with optionally a polyol and optionally a third polyfunctional crosslinking agent to form an oil phase; (e) Dissolve a water-soluble polymer in water to form an aqueous phase; (f) Combine the oil phase with the aqueous phase to form an oil-in-water emulsion; and (g) Apply the emulsion to a surface and dry and cure the emulsion on the surface to form the polymer or interpenetrating polymer network on the surface.

209. The polymer or interpenetrating polymer network according to claim 208, wherein a blocking agent is added to the oil phase after step (d) but before step (f).

210. The polymer or interpenetrating polymer network according to claim 208 or claim 209, wherein step (d) further comprises combining (i) the first adduct, (ii) the polyethyleneimine intermediate or the second adduct, and (iii) when present, the third adduct with optionally the polyol and optionally the third polyfunctional crosslinking agent in an organic solvent or diluent to form the oil phase.

211. The polymer or interpenetrating polymer network according to any one of claims 208 to 210, wherein step (d) further comprises adding a chain extender to the oil phase; or step (e) further comprises adding a chain extender to the aqueous phase; or a combination thereof.

212. The polymer or interpenetrating polymer network according to any one of claims 208 to 211, wherein step (e) further comprises adding a surfactant to the aqueous phase.

213. The polymer or interpenetrating polymer network according to any one of claims 208 to 211, wherein step (e) further comprises adding an antifoaming agent or defoaming agent to the aqueous phase.

214. The polymer or interpenetrating polymer network according to any one of claims 208 to 211, wherein step (e) further comprises adding either a surfactant or an antifoaming agent or defoaming agent to the aqueous phase.

215. The polymer or interpenetrating polymer network according to any one of claims 208 to 214, wherein step (f) further comprises performing a direct emulsification process, whereby the emulsion is formed by intense shear and mixing.

216. The polymer or interpenetrating polymer network according to any one of claims 208 to 214, wherein step (f) further comprises performing a direct emulsification process, whereby the emulsion is formed by sonication.

217. The polymer or interpenetrating polymer network according to any one of claims 208 to 214, wherein step (f) further comprises performing a phase inversion emulsification process, whereby a water-in-oil emulsion is first prepared and then phase inversion is carried out to form the oil-in-water emulsion.

218. The polymer or interpenetrating polymer network according to claim 217, wherein the phase inversion is carried out by changing any combination of the phase ratio, temperature, surfactant, solvent, or two or more of them.

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