Antibacterial coating composition

Abstract

Described herein are broad-spectrum antimicrobial quaternary ammonium polymers and interpenetrating polymer networks, and compositions thereof, that produce fast-acting, long-lasting, non-toxic, non-allergenic, colorless, transparent, and durable surface coatings that are resistant to water and common solvents. The surface coatings are easy and cost-effective to produce from readily available materials using versatile synthesis, allowing for a wide range of chemical variations. They are easily applied to a wide range of surfaces and materials without leaching of materials from the coating.

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims the benefit of priority to U.S. Provisional Patent Application No. 63 / 410,722, filed September 28, 2022, which is incorporated herein by reference in its entirety.

[0002] FIELD OF THE DISCLOSURE Embodiments of the present disclosure relate to broad-spectrum antimicrobial coating compositions and methods of using the same. More particularly, embodiments of the present disclosure relate to quaternary ammonium polymer structures and formulations with broad-spectrum antibacterial and antiviral properties. [Background technology]

[0003] Infectious diseases, including influenza, kill millions of people and sicken hundreds of millions worldwide each year. Since approximately 2020, the world has been experiencing the global COVID-19 pandemic caused by a highly contagious novel coronavirus, severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2).

[0004] SARS-CoV-2 coronavirus and / or other viruses before it have been shown to be transmitted from person to person as airborne droplets, but may also be transmitted by contact with virus-contaminated surfaces. A 2020 study conducted at two major urban hospitals in the United States found that 1 concluded that when commonly touched surfaces (e.g., keyboards, countertops, handrails, chairs) were coated with disinfectants, healthcare-associated infections were reduced by 36%. Indeed, surface disinfection has been adopted as a widespread health safety practice during the COVID-19 pandemic, but its effectiveness is limited because antiviral coatings lose their effectiveness after a short period of time, necessitating frequent reapplication, which is costly and labor-intensive.

[0005] Over the years, numerous antimicrobial polymers have been developed to provide more effective antibacterial / antiviral surface coatings. Jarach et al. (2020) 2 A recent review by highlights some of the different polymer approaches to this problem. These polymers include nanoparticles with bound or adsorbed drugs, nanoparticles with embedded antiviral metals, naturally occurring polymers such as chitosan, silica particles with adsorbed quaternary ammonium salts, and quaternary polyethyleneimine (PEI).

[0006] Desirable antimicrobial surface coatings have the following properties: (i) broad-spectrum antimicrobial activity with a low minimum inhibitory concentration (MIC), (ii) fast acting, (iii) long-lasting, (iv) non-toxic and non-allergenic, (v) no materials leaching from the coating, (vi) acceptable color, transparency, and appearance for a surface coating, (vii) easy application 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.

[0007] As recognized by the inventors of the present application, conventional antimicrobial surface coatings lack many of the above-listed characteristics. Accordingly, there is a need for improved antimicrobial surface coating compositions. Summary of the Invention

[0008] Embodiments of the present technology provide water-based quaternary ammonium polymer coating formulations that can be applied to a wide range of surfaces to render them broadly antimicrobial. Unlike conventional coatings, the water-based coatings disclosed herein (i) exhibit broad-spectrum antimicrobial activity with low minimum inhibitory concentrations (MICs), (ii) are fast-acting, (iii) are long-lasting, (iv) are non-toxic and non-allergenic, (v) do not leach materials from the coating, (vi) have acceptable color, transparency, and appearance for surface coatings, (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.

[0009] In one aspect, described herein is the use of reactive low-molecular-weight quaternary ammonium salts containing long-chain hydrophobic groups that render the salts highly surface-active and emulsifying effective in water. When the reactive quaternary ammonium salts are reacted with a multifunctional crosslinker (such as a polyisocyanate) and, optionally, an oligomeric polyol and / or a chain extender, the resulting reaction mixture can be readily emulsified in water with 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 drying and optional post-curing of the film. In some embodiments, the reactive low-molecular-weight quaternary ammonium salt contains a long-chain hydrophobic group on the nitrogen of the quaternary ammonium salt.

[0010] In another aspect, described herein is the use of reactive water-soluble protective colloids that form interpenetrating networks with the antimicrobial polymer in the oil phase to further improve the durability of the resulting coating.

[0011] In another aspect, described herein is the use of surface active polyols in the oil phase to further improve emulsion stability, reduce the particle size of the resulting emulsion, and improve coating quality.

[0012] In another aspect, described herein is the use of a blocking agent to protect the reaction product of a reactive surface-active quaternary ammonium salt with a multifunctional crosslinker prior to the emulsification step to further improve emulsion stability and processability or green time. The blocking agent is deblocked, for example, by heat or radiation during or after the drying and / or post-cure step, optionally in the presence of a catalyst or sensitizer, to obtain a durable coating.

[0013] The antibacterial efficacy of organic solvent-based antibacterial coatings generally decreases with increasing crosslink density of the coating. A high degree of crosslinking is often required to achieve acceptable coating properties, including durability and resistance to organic solvents, alcohols, water, detergents, and various disinfection solutions and processes. Unfortunately, bioactive functional groups in organic solvent-based coatings tend to become trapped in the crosslinked network at high crosslinking levels. Unlike such organic solvent-based antibacterial 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. As a result, durable coatings with desirable physical and chemical properties and high antibacterial efficacy can be simultaneously achieved by using the present technology.

[0014] In one aspect, an antimicrobial composition is provided comprising an oil-in-water emulsion, the oil-in-water emulsion comprising: (i) an oil phase comprising a first adduct of a first multifunctional crosslinker and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group reactive with the first multifunctional crosslinker, optionally a polyol, a polyethyleneimine intermediate, or a second adduct of the polyethyleneimine intermediate and a second multifunctional crosslinker, and optionally a third multifunctional crosslinker; and (ii) an aqueous phase comprising a water-soluble polymer, wherein the polyethyleneimine intermediate comprises an optionally substituted hydroxyalkylene functional group reactive with the first adduct and, if present, the second multifunctional crosslinker, and wherein nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized.

[0015] In one aspect, the water-soluble polymer is crosslinked with (a) a first multifunctional crosslinker incorporated in the first adduct, (b) a second multifunctional crosslinker, if present, incorporated in the second adduct, (c) a third multifunctional crosslinker, if present, or (d) any combination of two or more thereof.

[0016] In one aspect, the first quaternary ammonium salt is [ka] wherein: R 1 is -(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 Rq ) y10 -H, and -(CR m R n ) x11 -W 11 -(CR p R q ) y11 H—, —(C8-C 30 heteroalkyl), -(C8-C 30 Heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Aryl)-(C8-C 30 heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si; R 2 is -(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, -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 (aryl)-(C1-C4 heteroalkyl) has 1 to 2 heteroatoms independently selected from O, S, and Si; R 3 is -(C1-C 30 alkyl), -(C1-C 30 heteroalkyl), -(C1-C 30 Heteroalkyl)-(C6-C10 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, -(C1-C 30 heteroalkyl), -(C1-C 30 Heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Aryl)-(C1-C 30 heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si; A is -(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 -(C3-C 20 Heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; -(C3-C 20 alkylene)- and -(C3-C20 Heteroalkylene)- is -(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 is 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 5- to 6-membered cycloalkyl, C-C 10 selected from aryl, 5- to 6-membered heterocycloalkyl, and 5- to 6-membered heteroaryl, wherein heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si; x10 is an integer from 1 to 30, y10 is an integer from 0 to 29, and 8≦(x10+y10)≦30; x11 is an integer of 1 to 30, y11 is an integer of 0 to 29, and 8≦(x11+y11)≦30; x20 is an integer of 1 to 4, y20 is an integer of 0 to 3, and x20+y20≦4; x21 is an integer of 1 to 4, y21 is an integer of 0 to 3, and x21+y21≦4; x30 is an integer from 1 to 30, y30 is an integer from 0 to 29, and x30+y30≦30; x31 is an integer of 1 to 30, y31 is an integer of 0 to 29, and x31+y31≦30; x40 is an integer from 1 to 19, y40 is an integer from 1 to 19, and 3≦(x40+y40)≦20; x41 is an integer from 1 to 20, y41 is an integer from 0 to 19, and 3≦(x41+y41)≦20; Y is -OH, -NHR 4 , -SH, -COH, -C(O)NHR 4 , -C(S)NHR 4 , [ka] is selected from the group consisting of Each R 4 are independently 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), -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si; X - is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, borate, or an organically substituted derivative of any of the foregoing.

[0017] In one aspect, R 1 is -(C 12 -C 30 alkyl), -(C12 -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), -(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.

[0018] In one aspect, R 3 is -(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), -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 The (aryl)-(C1-C4 heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si.

[0019] In one aspect, R 2 and R 3 is methyl.

[0020] In one aspect, A is —(CH) m -or-(CH2CHR 5 -O-) n CH2CHR 5 wherein m is an integer from 2 to 20, n is 0, 1, 2, 3, 4, or 5, and each R 5 are independently 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), -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si.

[0021] In one aspect, each R 5 is independently H or methyl.

[0022] In one aspect, the first quaternary ammonium salt is [ka] Or a combination of two or more of them.

[0023] In one embodiment, the first quaternary ammonium salt is present in the oil phase in an amount of about 1% to about 50% by weight based on the dry weight of the oil phase.

[0024] In one embodiment, the first quaternary ammonium salt is present in the oil phase in an amount of about 5% to about 25% by weight based on the dry weight of the oil phase.

[0025] In one embodiment, the first multifunctional crosslinker incorporated in the first adduct is present in the oil phase in an amount of about 2% to about 25% by weight based on the dry weight of the oil phase.

[0026] In one embodiment, the first multifunctional crosslinker incorporated in the first adduct is present in the oil phase in an amount of about 5% to about 20% by weight based on the dry weight of the oil phase.

[0027] In one embodiment, the second multifunctional crosslinker incorporated in the second adduct is present in the oil phase in an amount of from about 0.1% to about 10% by weight based on the dry weight of the oil phase.

[0028] In one embodiment, the second multifunctional crosslinker incorporated in the second adduct is present in the oil phase in an amount of about 2% to about 8% by weight based on the dry weight of the oil phase.

[0029] In one embodiment, the third multifunctional crosslinker is present in the oil phase in an amount of from about 0.1% to about 20% by weight based on the dry weight of the oil phase.

[0030] In one embodiment, the third multifunctional crosslinker is present in the oil phase in an amount of about 2% to about 15% by weight based on the dry weight of the oil phase.

[0031] In one aspect, the first multifunctional crosslinker is a first polyisocyanate, the second multifunctional crosslinker, if present, is a second polyisocyanate, and the third multifunctional crosslinker, if present, is a third polyisocyanate, and the first polyisocyanate, second polyisocyanate, and third polyisocyanate are different.

[0032] In one aspect, the first multifunctional crosslinker is a first polyisocyanate, the second multifunctional crosslinker, if present, is a second polyisocyanate, the third multifunctional crosslinker, if present, is a third polyisocyanate, and the first polyisocyanate, second polyisocyanate, and third polyisocyanate are the same.

[0033] In one embodiment, the first, second, and third polyisocyanates each have an average isocyanate functionality of 2-5.

[0034] In one embodiment, the first, second, and third polyisocyanates each have an average isocyanate functionality of 3-4.

[0035] In one aspect, each of the first, second, and third polyisocyanates 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-cyclohexylisocyanate) (H12MDI), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

[0036] In one aspect, each of the first, second, and third polyisocyanates is independently selected from the group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T-series polyisocyanates, and LUPRANATE® M-series polyisocyanates.

[0037] In one embodiment, the first adduct has an average isocyanate functionality of 2-3.

[0038] In one embodiment, the first adduct has an average isocyanate functionality of from about 2.05 to about 2.3.

[0039] In one embodiment, the reactive isocyanate functional groups on the first adduct are blocked with a blocking agent.

[0040] In one embodiment, the blocking agent is selected from the group consisting of oximes, phenols, malonates, alcohols, lactams, dicarbonyl compounds, hydroxamates, bisulfite adducts, hydroxylamines, esters of p-hydroxybenzoic acid and salicylic acid.

[0041] In one embodiment, the blocking agent is selected from the group consisting of acetone oxime, methyl ethyl ketone oxime, sodium bisulfite, diethyl malonate, and 3,5-dimethylpyrazole.

[0042] In one aspect, the antimicrobial composition further comprises a deblocking agent.

[0043] In one aspect, the deblocking agent is selected from the group consisting of organotins, organobismuths, and tert-amines.

[0044] In one embodiment, the first adduct is present in the oil phase in an amount of about 5% to about 70% by weight based on the dry weight of the oil phase.

[0045] In one embodiment, the second adduct is present in the oil phase in an amount of from about 1% to about 30% by weight based on the dry weight of the oil phase.

[0046] In one embodiment, the second adduct is present in the oil phase in an amount of about 3% to about 15% by weight based on the dry weight of the oil phase.

[0047] In one embodiment, the oil phase further comprises an organic solvent or diluent.

[0048] In one embodiment, the organic solvent or diluent in the oil phase is water-miscible.

[0049] In one embodiment, the organic solvent or diluent is acetone.

[0050] In one embodiment, the organic solvent or diluent is present in the oil phase in an amount of from about 5% to about 35% by weight based on the weight of the oil phase.

[0051] In one embodiment, the organic solvent or diluent is present in the oil phase in an amount of from about 10% to about 30% by weight based on the weight of the oil phase.

[0052] In one aspect, the polyol, if present, 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.

[0053] In one aspect, 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).

[0054] In one embodiment, the polyol has a weight average molecular weight of about 300 to about 3,000.

[0055] In one embodiment, the polyol has a weight average molecular weight of about 400 to about 2,000.

[0056] In one embodiment, the polyol has a weight average molecular weight of about 600 to about 1,500.

[0057] In one embodiment, the polyol is present in the oil phase in an amount of from about 1% to about 40% by weight based on the dry weight of the oil phase.

[0058] In one embodiment, the polyol is present in the oil phase in an amount of from about 5% to about 25% by weight based on the dry weight of the oil phase.

[0059] In one aspect, 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 intermediates, copolymers of two or more thereof, copolymers of one or more thereof with polyvinylpyrrolidone poly(glycidyl acrylate) or poly(glycidyl methacrylate), and combinations or blends of two or more thereof.

[0060] In one embodiment, the water-soluble polymer is hydroxyethyl cellulose or a hydrophobically modified derivative thereof.

[0061] In one embodiment, the water-soluble polymer is a polyethyleneimine intermediate.

[0062] In one embodiment, the water-soluble polymer is present in the aqueous phase in an amount of from about 0.5% to about 15% by weight of the dry weight of the oil phase.

[0063] In one embodiment, the water-soluble polymer is present in the aqueous phase in an amount of from about 3% to about 12% by weight of the dry weight of the oil phase.

[0064] In one embodiment, the water-soluble polymer is present in the aqueous phase in an amount of about 5% to about 10% by weight of the dry weight of the oil phase.

[0065] In one embodiment, the aqueous phase further comprises a surfactant.

[0066] In one embodiment, the surfactant is a non-ionic surfactant.

[0067] In one embodiment, the nonionic surfactant has an average HLB (hydrophile-lipophile balance) value of about 12 to about 15.

[0068] In one aspect, the non-ionic surfactant is selected from TRITON® X-114 ((1,1,3,3-tetramethylbutyl)phenyl-polyethylene glycol), SILWET™ L-7604 (siloxane polyalkylene oxide copolymer), and combinations thereof.

[0069] In one embodiment, the surfactant is present in the aqueous phase in an amount of from about 0.05% to about 2% by weight based on the dry weight of the oil phase.

[0070] In one embodiment, the surfactant is present in the aqueous phase in an amount of from about 0.1% to about 1% by weight based on the dry weight of the oil phase.

[0071] In one embodiment, the aqueous phase further comprises a defoamer or anti-foaming agent.

[0072] In one embodiment, the antifoam agent is FOAMSTAR® ST 2410 (a star polymer-based antifoam agent).

[0073] In one aspect, the random polymer or interpenetrating polymer network is produced from the random polymerization / crosslinking of a first adduct, a polyethyleneimine intermediate or a second adduct, if present, a polyol, a water-soluble polymer, if reactive, and a third multifunctional crosslinker, if present.

[0074] In one embodiment, the oil phase comprises a first multifunctional crosslinker and a second quaternary ammonium salt. [ka] wherein: R 1a , R 2a , and R 3a are each independently methyl or ethyl; A 1 is -(C3-C 20 alkylene)-, -(C3-C 20 heteroalkylene)-, -(C6-C 10 Arylene)-(C3-C20 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 -(C3-C 20 Heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; -(C3-C 20 alkylene)- and -(C3-C 20 Heteroalkylene)- is -(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 is selected from —C(O)—, —C(O)O—, —OC(O)—, —C(O)NH—, and —NHC(O)—; W 43 is a 5- to 6-membered cycloalkyl, C6-C 10 selected from aryl, 5- to 6-membered heterocycloalkyl, and 5- to 6-membered heteroaryl, wherein heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si; x42 is an integer from 1 to 19, y42 is an integer from 1 to 19, and 3≦(x42+y42)≦20; x43 is an integer from 1 to 20, y43 is an integer from 0 to 19, and 3≦(x43+y43)≦20; Y 1 -OH, -NHR 4a , -SH, -COH, -C(O)NHR 4a , -C(S)NHR 4a , [ka] is selected from the group consisting of Each R 4a are independently 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), -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si; X - is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, borate, or an organically substituted derivative of any of the foregoing.

[0075] In one embodiment, the oil phase comprises a fourth multifunctional crosslinker and a second quaternary ammonium salt. [ka] wherein: R 1a , R 2a , and R3a are each independently methyl or ethyl; A 1 is -(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 -(C3-C 20 Heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; -(C3-C 20 alkylene)- and -(C3-C 20 Heteroalkylene)- is -(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 is selected from —C(O)—, —C(O)O—, —OC(O)—, —C(O)NH—, and —NHC(O)—; W 43 is a 5- to 6-membered cycloalkyl, C6-C 10selected from aryl, 5- to 6-membered heterocycloalkyl, and 5- to 6-membered heteroaryl, wherein heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si; x42 is an integer from 1 to 19, y42 is an integer from 1 to 19, and 3≦(x42+y42)≦20; x43 is an integer from 1 to 20, y43 is an integer from 0 to 19, and 3≦(x43+y43)≦20; Y 1 -OH, -NHR 4a , -SH, -COH, -C(O)NHR 4a , -C(S)NHR 4a , [ka] is selected from the group consisting of Each R 4a are independently 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), -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si; X - is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, borate, or an organically substituted derivative of any of the foregoing.

[0076] In one embodiment, the fourth multifunctional crosslinker is different from the first multifunctional crosslinker, and, if present, the second multifunctional crosslinker, and, if present, the third multifunctional crosslinker.

[0077] In one embodiment, the fourth polyisocyanate is present in the oil phase in an amount of from about 0.1% to about 15% by weight based on the dry weight of the oil phase.

[0078] In one embodiment, the fourth multifunctional crosslinker is a fourth polyisocyanate.

[0079] In one embodiment, the fourth polyisocyanate has an average isocyanate functionality of 2-5.

[0080] In one embodiment, 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-cyclohexylisocyanate) (H12MDI), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

[0081] In one aspect, the fourth polyisocyanate is selected from the group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T-series polyisocyanates, and LUPRANATE® M-series polyisocyanates.

[0082] In one aspect, the second quaternary ammonium salt is [ka] is.

[0083] In one embodiment, the second quaternary ammonium salt is present in the oil phase in an amount of about 1% to about 15% by weight based on the dry weight of the oil phase.

[0084] In one embodiment, the second quaternary ammonium salt is present in the oil phase in an amount of about 3% to about 10% by weight based on the dry weight of the oil phase.

[0085] In one embodiment, the third adduct has an average isocyanate functionality of 2-3.

[0086] In one embodiment, the third adduct has an average isocyanate functionality of from about 2.05 to about 2.3.

[0087] In one embodiment, the third adduct is present in the oil phase in an amount of about 2% to about 30% by weight based on the dry weight of the oil phase.

[0088] In one embodiment, the reactive isocyanate functional groups on the third adduct are blocked with a blocking agent.

[0089] In one embodiment, the blocking agent for the reactive isocyanate functional group on the third adduct is selected from the group consisting of oximes, phenols, malonates, alcohols, lactams, dicarbonyl compounds, hydroxamates, bisulfite adducts, hydroxylamines, esters of p-hydroxybenzoic acid and salicylic acid.

[0090] In one embodiment, the blocking agent for the reactive isocyanate functionality on the third adduct is selected from the group consisting of acetone oxime, methyl ethyl ketone oxime, sodium bisulfite, diethyl malonate, and 3,5-dimethylpyrazole.

[0091] In one aspect, the random polymer or interpenetrating polymer network is produced from the random polymerization / crosslinking of a first adduct, a polyethyleneimine intermediate or second adduct, a third adduct, if present, a polyol, a water-soluble polymer, if reactive, and a third multifunctional crosslinker, if present.

[0092] In one embodiment, the oil phase is HO—(C n H 2n )-OH and HO-(C n H 2n-2 )—OH, or combinations thereof, wherein n is an integer from 2 to 8.

[0093] In one embodiment, the chain extender is propanediol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexanedimethanol, or a combination of two or more thereof.

[0094] In one embodiment, 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.

[0095] In one embodiment, the chain extender is present in the oil phase in an amount of from about 0.5% to about 10% by weight based on the dry weight of the oil phase.

[0096] In one aspect, the random polymer or interpenetrating polymer network is produced from the random polymerization / crosslinking of the first adduct, the polyethyleneimine intermediate or second adduct, if present, the third adduct, if present, the polyol, the chain extender, the water-soluble polymer, if reactive, and the third multifunctional crosslinker, if present.

[0097] In one embodiment, the polyethyleneimine intermediate is present in the oil phase in an amount of from about 0.1% to about 50% by weight based on the dry weight of the oil phase.

[0098] In one aspect, the hydroxyalkylene functional group is -N + (R 20 )3X - , -(C6-C 10 aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10aryl), and carboxy; and each R 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl, and each X - is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

[0099] In one embodiment, the hydroxyalkylene functional group is hydroxyethylene, hydroxypropylene, hydroxybutylene, or oligomers thereof.

[0100] In one aspect, the polyethyleneimine intermediate comprises the reaction product of a polyethyleneimine, a monoepoxide, and a reagent comprising an alkylating agent, wherein the monoepoxide is —(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with hydroxy, C1-C6 alkoxy, C6-C6 optionally substituted with C1-C6 alkyl 10 Optionally substituted with C1-C6 alkyl optionally substituted with a substituent selected from aryl, and carboxy.

[0101] In one embodiment, the monoepoxide is a C1-C6 alkyl epoxide.

[0102] In one aspect, the C1-C6 alkyl epoxide is selected from the group consisting of propyl epoxide, butyl epoxide, and hexyl epoxide.

[0103] In one aspect, the polyethyleneimine intermediate comprises the reaction product of a polyethyleneimine, a monoepoxide, and optionally a reagent comprising an alkylating agent, wherein the monoepoxide is -(C1-C6 alkyl)-N + (R 20 )3X - and each R 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl, and each X - is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

[0104] In one embodiment, the alkylating agent comprises one or more R 21 -LG, wherein each R 21 are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 and —(C1-C6 alkoxy) optionally substituted with —OH, wherein each LG is a leaving group.

[0105] In one embodiment, the alkylating agent is a benzyl halide or a hexyl halide.

[0106] In one aspect, the polyethyleneimine intermediate comprises the reaction product of a reagent comprising polyethyleneimine and a haloalkanol.

[0107] In one aspect, the haloalkanol is X 30 -(C2-C6 alkylene)-OH, and X 30 is Cl, Br, or I.

[0108] In one embodiment, the reagents for the reaction product comprised in the polyethyleneimine intermediate further comprise a monoisocyanate.

[0109] In one aspect, the monoisocyanate comprises one or more R 30 -NCO, wherein each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 alkyl, and (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, 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.

[0110] In one aspect, the monoisocyanate comprises octyl isocyanate, octadecyl isocyanate, or a combination thereof.

[0111] In one embodiment, the polyethyleneimine has a molecular weight of about 300 to about 270,000 daltons.

[0112] In one embodiment, the polyethyleneimine has a molecular weight of about 10,000 to about 200,000 daltons.

[0113] In one embodiment, the polyethyleneimine has a molecular weight of about 25,000 to about 120,000 daltons.

[0114] In one embodiment, the polyethyleneimine is branched.

[0115] In one embodiment, the polyethyleneimine is hyperbranched.

[0116] In one embodiment, the polyethyleneimine has a ratio of primary to secondary to tertiary amines of about 1:2:1 to about 1:1:1.

[0117] In one embodiment, the polyethyleneimine has a ratio of primary to secondary to tertiary amines of about 1:1:0.7.

[0118] In one aspect, the polyethyleneimine intermediate is [ka] or a copolymer of any two or more thereof, wherein: Each Y 3 are independently H or -OY 2 and for all Y 3 But it cannot be H, Each Y 2 are independently H or -C(O)-NHR 30 and for all Y 2 -C(O)-NHR 30 It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10are independently hydrogen; -N + (R 20 )3X - , -(C6-C 10 aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy; 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl; Each R 21 are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 C1-C6 alkyl optionally substituted with a substituent selected from -(aryl), and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 alkyl, and (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, wherein each Ra 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 X - are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and organically substituted derivatives thereof; however, R 10 But -(C6-C 10 aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy, the polyethyleneimine intermediate is [ka] The condition is that the item is selected from the following:

[0119] In one aspect, the polyethyleneimine intermediate is [ka] wherein each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000.

[0120] In one embodiment, at least 20% of the nitrogen atoms of the polyethyleneimine intermediate are quaternized.

[0121] In one embodiment, the second adduct is of formula (I): [ka] During the ceremony, Each A is independently [ka] or a copolymer of any two or more thereof, wherein the attachment of each A forms a carbamate linkage; Each Y 3 are independently H or -OY 2 and for all Y 3 But it cannot be H, Each Y 2 are independently H or -C(O)-NHR 30 and for all Y 2 -C(O)-NHR 30 It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 are independently hydrogen; -N + (R 20 )3X - , -(C6-C 10 aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy; 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl; Each R 21are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 C1-C6 alkyl optionally substituted with a substituent selected from -(aryl), and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 Alkyl, (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, and (3) [ka] 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 are independently -(C-C optionally substituted with phenyl) 10 alkylene)- or a 3- to 8-membered cycloalkyl ring; each X - are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and organically substituted derivatives thereof; however, R 10 But -(C6-C 10aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy, each A is independently [ka] The condition is that the item is selected from the following:

[0122] In one embodiment, the second adduct is of formula (II): [ka] During the ceremony, Each A is independently [ka] or a copolymer of any two or more thereof, wherein the attachment of each A forms a carbamate linkage; Each Y 3 are independently H or -OY 2 and for all Y 3 But it cannot be H, Each Y 2 are independently H or -C(O)-NHR 30 and for all Y 2 -C(O)-NHR 30 It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 are independently hydrogen; -N + (R 20 )3X - , -(C6-C 10aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy; 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl; Each R 21 are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 C1-C6 alkyl optionally substituted with a substituent selected from -(aryl), and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 Alkyl, (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, and (3) [ka] wherein each Ra 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 are independently -(C-C optionally substituted with phenyl) 10 alkylene)- or a 3- to 8-membered cycloalkyl ring; each X - are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and organically substituted derivatives thereof; however, R 10 But -(C6-C 10 aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy, each A is independently [ka] The condition is that the item is selected from the following:

[0123] A polymer or interpenetrating polymer network is provided that comprises the random polymerization / crosslinking product of reagents including (i) a first adduct of a first multifunctional crosslinker and a first quaternary ammonium salt, (ii) a polyol, (iii) a polyethyleneimine intermediate or a second adduct of a polyethyleneimine intermediate and a second multifunctional crosslinker, and (iv) optionally a third multifunctional crosslinker.

[0124] In one embodiment, in the polymer or interpenetrating polymer network, the first quaternary ammonium salt is [ka] wherein: R 1 is -(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—, —(C8-C 30 heteroalkyl), -(C8-C 30 Heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Aryl)-(C8-C 30 heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si; R 2 is -(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, -(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; R 3 is -(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, -(C1-C 30 heteroalkyl), -(C1-C 30 Heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Aryl)-(C1-C 30 heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si; A is -(C3-C 20 alkylene)-, -(C3-C 20 heteroalkylene)-, -(C6-C10 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 -(C3-C 20 Heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; -(C3-C 20 alkylene)- and -(C3-C 20 Heteroalkylene)- is -(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 is 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 5- to 6-membered cycloalkyl, C-C 10selected from aryl, 5- to 6-membered heterocycloalkyl, and 5- to 6-membered heteroaryl, wherein heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si; x10 is an integer from 1 to 30, y10 is an integer from 0 to 29, and 8≦(x10+y10)≦30; x11 is an integer of 1 to 30, y11 is an integer of 0 to 29, and 8≦(x11+y11)≦30; x20 is an integer of 1 to 4, y20 is an integer of 0 to 3, and x20+y20≦4; x21 is an integer of 1 to 4, y21 is an integer of 0 to 3, and x21+y21≦4; x30 is an integer from 1 to 30, y30 is an integer from 0 to 29, and x30+y30≦30; x31 is an integer of 1 to 30, y31 is an integer of 0 to 29, and x31+y31≦30; x40 is an integer from 1 to 19, y40 is an integer from 1 to 19, and 3≦(x40+y40)≦20; x41 is an integer from 1 to 20, y41 is an integer from 0 to 19, and 3≦(x41+y41)≦20; Y is -OH, -NHR 4 , -SH, -COH, -C(O)NHR 4 , -C(S)NHR 4 , [ka] is selected from the group consisting of Each R 4 are independently 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 10aryl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si; X - is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, borate, or an organically substituted derivative of any of the foregoing.

[0125] In one embodiment of the polymer or interpenetrating polymer network, R 1 is -(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), -(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.

[0126] In one embodiment of the polymer or interpenetrating polymer network, R 3is -(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), -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 The (aryl)-(C1-C4 heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si.

[0127] In one embodiment of the polymer or interpenetrating polymer network, R 2 and R 3 is methyl.

[0128] In one embodiment of the polymer or interpenetrating polymer network, A is —(CH) m -or-(CH2CHR 5 -O-) n CH2CHR 5 wherein m is an integer from 2 to 20, n is 0, 1, 2, 3, 4, or 5, and each R 5 are independently 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), -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si.

[0129] In one embodiment of the polymer or interpenetrating polymer network, R 5 is H or methyl.

[0130] In one embodiment of the polymer or interpenetrating polymer network, the first quaternary ammonium salt is [ka] Or a combination of two or more of them.

[0131] In one embodiment 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 from about 1% to about 50% by weight.

[0132] In one aspect of the polymer or interpenetrating polymer network, the first multifunctional crosslinker is a first polyisocyanate, the second multifunctional crosslinker, if present, is a second polyisocyanate, and the third multifunctional crosslinker, if present, is a third polyisocyanate, and the first polyisocyanate, second polyisocyanate, and third polyisocyanate are different.

[0133] In one aspect of the polymer or interpenetrating polymer network, the first multifunctional crosslinker is a first polyisocyanate, the second multifunctional crosslinker, if present, is a second polyisocyanate, the third multifunctional crosslinker, if present, is a third polyisocyanate, and the first polyisocyanate, second polyisocyanate, and third polyisocyanate are the same.

[0134] In one embodiment of the polymer or interpenetrating polymer network, the first, second, and third polyisocyanates each have an average isocyanate functionality of 2-5.

[0135] In one embodiment of the polymer or interpenetrating polymer network, the first, third, and third polyisocyanates each have an average isocyanate functionality of 3 to 4.

[0136] In one embodiment of the polymer or interpenetrating polymer network, each of the first, second, and third polyisocyanates 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), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

[0137] In one embodiment of the polymer or interpenetrating polymer network, each of the first, second, and third polyisocyanates is independently selected from the group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T-series polyisocyanates, and LUPRANATE® M-series polyisocyanates.

[0138] In one embodiment of the polymer or interpenetrating polymer network, the first multifunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of from about 2% to about 25% by weight.

[0139] In one embodiment of the polymer or interpenetrating polymer network, the second multifunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1% to about 10% by weight.

[0140] In one embodiment of the polymer or interpenetrating polymer network, the third multifunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1% to about 20% by weight.

[0141] In one embodiment of the polymer or interpenetrating polymer network, the first adduct has an average isocyanate functionality of 2 to 3.

[0142] In one embodiment of the polymer or interpenetrating polymer network, the first adduct has an average isocyanate functionality of from about 2.05 to about 2.3.

[0143] 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.

[0144] In one embodiment 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).

[0145] In one embodiment of the polymer or interpenetrating polymer network, the polyol has a weight average molecular weight of about 300 to about 3,000.

[0146] In one embodiment of the polymer or interpenetrating polymer network, the polyol has a weight average molecular weight of about 400 to about 2000.

[0147] In one embodiment of the polymer or interpenetrating polymer network, the polyol has a weight average molecular weight of from about 600 to about 1500.

[0148] In one embodiment 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% to about 40% by weight.

[0149] In one embodiment of the polymer or interpenetrating polymer network, the reagents include a first multifunctional crosslinker and a second quaternary ammonium salt. [ka] wherein: R 1a , R 2a , and R 3a are each independently methyl or ethyl; A 1 is -(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 -(C3-C 20 Heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; -(C3-C 20 alkylene)- and -(C3-C 20 Heteroalkylene)- is -(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-C10 aryl); Each R m1 , R n1 , R p1 , and R q1 is independently selected from H and C1-C4 alkyl; W 42 is selected from —C(O)—, —C(O)O—, —OC(O)—, —C(O)NH—, and —NHC(O)—; W 43 is a 5- to 6-membered cycloalkyl, C6-C 10 selected from aryl, 5- to 6-membered heterocycloalkyl, and 5- to 6-membered heteroaryl, wherein heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si; x42 is an integer from 1 to 19, y42 is an integer from 1 to 19, and 3≦(x42+y42)≦20; x43 is an integer from 1 to 20, y43 is an integer from 0 to 19, and 3≦(x43+y43)≦20; Y 1 -OH, -NHR 4a , -SH, -COH, -C(O)NHR 4a , -C(S)NHR 4a , [ka] is selected from the group consisting of Each R 4a are independently 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), -(C6-C 10aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si; X - is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, borate, or an organically substituted derivative of any of the foregoing.

[0150] In one embodiment of the polymer or interpenetrating polymer network, the reagent comprises a fourth multifunctional crosslinker and a second quaternary ammonium salt. [ka] wherein: R 1a , R 2a , and R 3a are each independently methyl or ethyl; A 1 is -(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 -(C3-C 20 Heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; -(C3-C 20 alkylene)- and -(C3-C 20Heteroalkylene)- is -(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 is selected from —C(O)—, —C(O)O—, —OC(O)—, —C(O)NH—, and —NHC(O)—; W 43 is a 5- to 6-membered cycloalkyl, C6-C 10 selected from aryl, 5- to 6-membered heterocycloalkyl, and 5- to 6-membered heteroaryl, wherein heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si; x42 is an integer from 1 to 19, y42 is an integer from 1 to 19, and 3≦(x42+y42)≦20; x43 is an integer from 1 to 20, y43 is an integer from 0 to 19, and 3≦(x43+y43)≦20; Y 1 -OH, -NHR 4a , -SH, -COH, -C(O)NHR 4a , -C(S)NHR 4a , [ka] is selected from the group consisting of Each R 4a are independently H, -(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si; X - is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, borate, or an organically substituted derivative of any of the foregoing.

[0151] In one embodiment, the fourth multifunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1% to about 15% by weight.

[0152] In one embodiment of the polymer or interpenetrating polymer network, the fourth multifunctional crosslinker is different from the first multifunctional crosslinker, and, if present, the second multifunctional crosslinker, and, if present, the third multifunctional crosslinker.

[0153] In one embodiment of the polymer or interpenetrating polymer network, the fourth multifunctional crosslinker is a fourth polyisocyanate.

[0154] In one embodiment of the polymer or interpenetrating polymer network, each of the fourth polyisocyanates 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), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

[0155] In one embodiment of the polymer or interpenetrating polymer network, the fourth polyisocyanate is selected from the group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T-series polyisocyanates, and LUPRANATE® M-series polyisocyanates.

[0156] In embodiments of the polymer or interpenetrating polymer network, the second quaternary ammonium salt is [ka] is.

[0157] In one embodiment 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 from about 1% to about 15% by weight.

[0158] In one embodiment of the polymer or interpenetrating polymer network, the third adduct has an average isocyanate functionality of 2 to 3.

[0159] In one embodiment of the polymer or interpenetrating polymer network, the third adduct has an average isocyanate functionality of from about 2.05 to about 2.3.

[0160] In one embodiment of the polymer or interpenetrating polymer network, the third adduct is present in the dry polymer or interpenetrating polymer network in an amount of from about 2% to about 30% by weight.

[0161] In one embodiment of the polymer or interpenetrating polymer network, the polyethyleneimine intermediate is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1% to about 50% by weight.

[0162] In one aspect of the polymer or interpenetrating polymer network, the polyethyleneimine intermediate comprises a first adduct and, if present, an optionally substituted hydroxyalkylene functional group that reacts with the second multifunctional crosslinker.

[0163] In one embodiment of the polymer or interpenetrating polymer network, the hydroxy alkylene functionality is -N + (R 20 )3X - , -(C6-C 10 aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy; and each R 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl, and each X -is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

[0164] In one embodiment of the polymer or interpenetrating polymer network, the hydroxyalkylene functional group is hydroxyethylene, hydroxypropylene, hydroxybutylene, or oligomers thereof.

[0165] In one embodiment of the polymer or interpenetrating polymer network, the polyethyleneimine intermediate comprises the reaction product of a polyethyleneimine, a monoepoxide, and a reagent comprising an alkylating agent, wherein the monoepoxide is —(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with hydroxy, C1-C6 alkoxy, C6-C6 optionally substituted with C1-C6 alkyl 10 Optionally substituted with C1-C6 alkyl optionally substituted with a substituent selected from aryl, and carboxy.

[0166] In one embodiment of the polymer or interpenetrating polymer network, the monoepoxide is a C1-C6 alkyl epoxide.

[0167] In one embodiment 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.

[0168] In one aspect of the polymer or interpenetrating polymer network, the polyethyleneimine intermediate comprises the reaction product of a polyethyleneimine, a monoepoxide, and optionally a reagent comprising an alkylating agent, wherein the monoepoxide is a (C1-C6 alkyl)-N + (R 20 )3X - and each R 20 are independently C1-C18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl, and each X - is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

[0169] In one embodiment of the polymer or interpenetrating polymer network, the alkylating agent comprises one or more R 21 -LG, wherein each R 21 are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 and —(C1-C6 alkoxy) optionally substituted with —OH, wherein each LG is a leaving group.

[0170] In one embodiment of the polymer or interpenetrating polymer network, the alkylating agent is a benzyl halide or a hexyl halide.

[0171] In one aspect of the polymer or interpenetrating polymer network, the polyethyleneimine intermediate comprises the reaction product of a reagent comprising polyethyleneimine and a haloalkanol.

[0172] In one embodiment of the polymer or interpenetrating polymer network, the haloalkanol is X 30-(C2-C6 alkylene)-OH, and X 30 is Cl, Br, or I.

[0173] In one embodiment of the polymer or interpenetrating polymer network, the reagents for the reaction product included in the polyethyleneimine intermediate further comprise a monoisocyanate.

[0174] In one embodiment of the polymer or interpenetrating polymer network, the monoisocyanate may comprise one or more R 30 -NCO, wherein each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 alkyl, and (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, 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.

[0175] In one aspect of the polymer or interpenetrating polymer network, the monoisocyanate comprises octyl isocyanate, octadecyl isocyanate, or a combination thereof.

[0176] In one embodiment of the polymer or interpenetrating polymer network, the polyethyleneimine has a molecular weight of from about 300 to about 270,000 daltons.

[0177] In one embodiment of the polymer or interpenetrating polymer network, the polyethyleneimine has a molecular weight of about 10,000 to about 200,000 daltons.

[0178] In one embodiment of the polymer or interpenetrating polymer network, the polyethyleneimine has a molecular weight of about 25,000 to about 120,000 daltons.

[0179] In one aspect of the polymer or interpenetrating polymer network, the polyethyleneimine is branched.

[0180] In one aspect of the polymer or interpenetrating polymer network, the polyethyleneimine is hyperbranched.

[0181] In one embodiment of the polymer or interpenetrating polymer network, the polyethyleneimine has a ratio of primary to secondary to tertiary amines of about 1:2:1 to about 1:1:1.

[0182] In one embodiment of the polymer or interpenetrating polymer network, the polyethyleneimine has a ratio of primary to secondary to tertiary amines of about 1:1:0.7.

[0183] In one aspect of the polymer or interpenetrating polymer network, the polyethyleneimine intermediate is [ka] or a copolymer of any two or more thereof, wherein: Each Y 3 are independently H or -OY 2 and for all Y 3 But it cannot be H, Each Y 2 are independently H or -C(O)-NHR 30 and for all Y 2 -C(O)-NHR 30 It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 are independently hydrogen; -N(R 20 )3, -(C6-C 10 aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy; 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl; Each R 21 are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 C1-C6 alkyl optionally substituted with a substituent selected from -(aryl), and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 alkyl, and (2) halogen, -(C1-C6 alkyl), and -SiR a (ORb )(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, 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 X - are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and organically substituted derivatives thereof; however, R 10 But -(C6-C 10 aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy, the polyethyleneimine intermediate is [ka] The condition is that the item is selected from the following:

[0184] In one aspect of the polymer or interpenetrating polymer network, the polyethyleneimine intermediate is [ka] wherein each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000.

[0185] In one embodiment of the polymer or interpenetrating polymer network, the second adduct is of formula (I): [ka] During the ceremony, Each A is independently [ka] or a copolymer of any two or more thereof, wherein the attachment of each A forms a carbamate linkage; Each Y 3 are independently H or -OY 2 and for all Y 3 But it cannot be H, Each Y 2 are independently H or -C(O)-NHR 30 and for all Y 2 -C(O)-NHR 30 It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 are independently hydrogen; -N(R 20 )3, -(C6-C 10 aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy; 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl; Each R 21are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 C1-C6 alkyl optionally substituted with a substituent selected from -(aryl), and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 Alkyl, (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, and (3) [ka] 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 are independently -(C-C optionally substituted with phenyl) 10 alkylene)- or a 3- to 8-membered cycloalkyl ring; each X - are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and organically substituted derivatives thereof; however, R 10 But -(C6-C 10aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy, each A is independently [ka] The condition is that the item is selected from the following:

[0186] In one embodiment of the polymer or interpenetrating polymer network, the second adduct is of formula (II): [ka] During the ceremony, Each A is independently [ka] or a copolymer of any two or more thereof, wherein the attachment of each A forms a carbamate linkage; Each Y 3 are independently H or -OY 2 and for all Y 3 But it cannot be H, Each Y 2 are independently H or -C(O)-NHR 30 and for all Y 2 -C(O)-NHR 30 It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 are independently hydrogen; -N(R 20 )3, -(C6-C 10 aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C10 aryl), and carboxy; 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl; Each R 21 are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 C1-C6 alkyl optionally substituted with a substituent selected from -(aryl), and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 Alkyl, (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, and (3) [ka] wherein each R a is independently -(C1-C6 alkyl), and each R b and each R cis independently selected from —(C1-C6 alkyl) and —Si(C1-C6 alkyl)3; Each R 40 are independently -(C-C optionally substituted with phenyl) 10 alkylene)- or a 3- to 8-membered cycloalkyl ring; each X - are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and organically substituted derivatives thereof; however, R 10 But -(C6-C 10 aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy, each A is independently [ka] The condition is that the item is selected from the following:

[0187] In one embodiment of the polymer or interpenetrating polymer network, the second adduct is present in the dry polymer or interpenetrating polymer network in an amount of from about 1% to about 30% by weight.

[0188] In one embodiment of the polymer or interpenetrating polymer network, the random polymerization / crosslinking product reagents included in the polymer or interpenetrating polymer network further comprise a water-soluble polymer.

[0189] In one aspect of the polymer or interpenetrating polymer network, the water-soluble polymer is crosslinked with (a) a first multifunctional crosslinker incorporated in the first adduct, (b) a second multifunctional crosslinker, if present, incorporated in the second adduct, (c) a third multifunctional crosslinker, if present, or (d) any combination of two or more thereof.

[0190] In one embodiment 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% to about 15% by weight.

[0191] In one embodiment 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 intermediates, copolymers of two or more thereof, copolymers of one or more thereof with polyvinylpyrrolidone poly(glycidyl acrylate) or poly(glycidyl methacrylate), and combinations or blends of two or more thereof.

[0192] In one embodiment of the polymer or interpenetrating polymer network, the water-soluble polymer is hydroxyethyl cellulose or a hydrophobically modified derivative thereof.

[0193] In one aspect of the polymer or interpenetrating polymer network, the water-soluble polymer is another polyethyleneimine intermediate.

[0194] In one embodiment of the polymer or interpenetrating polymer network, the reagent for random polymerization / crosslinking products included in the polymer or interpenetrating polymer network is HO—(C n H2n )-OH and HO-(C n H 2n-2 )—OH, or combinations thereof, wherein n is an integer from 2 to 8.

[0195] In one embodiment of the polymer or interpenetrating polymer network, the chain extender is propanediol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexanedimethanol, or a combination of two or more thereof.

[0196] In one embodiment 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% to about 10% by weight.

[0197] In one aspect, a composition is provided that includes the above-described polymer or interpenetrating polymer network.

[0198] In one aspect, [ka] or a copolymer of any two or more thereof, wherein: Each Y 3 are independently H or -OY 2 and for all Y 3 But it cannot be H, Each Y 2 are independently H or -C(O)-NHR 30 and for all Y 2 -C(O)-NHR 30 It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 -N + (R 20 )3X -and each R 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl; Each R 21 are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 C1-C6 alkyl optionally substituted with a substituent selected from -(aryl), and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 alkyl, and (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, 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 X -is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

[0199] In one aspect, in the aforementioned antibacterial compounds, each Y 2 is H.

[0200] In one aspect, in the aforementioned antibacterial compound, the compound is [ka] wherein each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000.

[0201] In one aspect, a random polymerization product of a polyethyleneimine intermediate and a crosslinker is provided, wherein the polyethyleneimine intermediate comprises: [ka] or a copolymer of any two or more thereof, wherein: Each Y 3 are independently H or -OY 2 and for all Y 3 But it cannot be H, Each Y 2 are independently H or -C(O)-NHR 30 and for all Y 2 -C(O)-NHR 30 It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 -N + (R 20 )3X - and each R20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl; Each R 21 are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 C1-C6 alkyl optionally substituted with a substituent selected from -(aryl), and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 alkyl, and (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, 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 X -is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

[0202] In one embodiment of the random polymerization product, the crosslinker is a polyisocyanate.

[0203] In one embodiment of the random polymerization product, 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), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

[0204] In one embodiment of the random polymerization product, the polyisocyanates are independently selected from the group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T-series polyisocyanates, and LUPRANATE® M-series polyisocyanates.

[0205] In one embodiment of the random polymerization product, the random polymerization product is of formula (I): [ka] During the ceremony, Each A is independently [ka] or a copolymer of any two or more thereof, wherein the attachment of each A forms a carbamate linkage; Each Y3 are independently H or -OY 2 and for all Y 3 But it cannot be H, Each Y 2 are independently H or -C(O)-NHR 30 and for all Y 2 -C(O)-NHR 30 It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 -N + (R 20 )3X - and each R 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl; Each R 21 are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 C1-C6 alkyl optionally substituted with a substituent selected from -(aryl), and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from20 Alkyl, (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, and (3) [ka] 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 are independently -(C-C optionally substituted with phenyl) 10 alkylene)- or a 3- to 8-membered cycloalkyl ring; each X - is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

[0206] In one embodiment of the random polymerization product, the random polymerization product is of formula (II): [ka] During the ceremony, Each A is independently [ka] or a copolymer of any two or more thereof, wherein the attachment of each A forms a carbamate linkage; Each Y 3 are independently H or -OY 2 and for all Y 3 But it cannot be H, Each Y 2are independently H or -C(O)-NHR 30 and for all Y 2 -C(O)-NHR 30 It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 -N + (R 20 )3X - and each R 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl; Each R 21 are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 C1-C6 alkyl optionally substituted with a substituent selected from -(aryl), and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 Alkyl, (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR cC6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, and (3) [ka] 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 are independently -(C-C optionally substituted with phenyl) 10 alkylene)- or a 3- to 8-membered cycloalkyl ring; each X - is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

[0207] In one aspect, a composition is provided that includes the antimicrobial compound described above.

[0208] In one aspect, a composition is provided comprising the random polymerization product described above.

[0209] In one aspect, there is provided an antimicrobial coating, coating fluid, or spray fluid comprising the above-described composition.

[0210] In one aspect, there is provided a device, apparatus, equipment, or accessory comprising the above-described coating, coating fluid, or spray fluid.

[0211] In one aspect, in the device, equipment, apparatus, or accessory, the coating or spraying fluid is water-soluble or water-dispersible.

[0212] In one aspect, the device, equipment, apparatus, or accessory is selected from the group consisting of a filter, an air purifier, and a mask.

[0213] In one aspect, the device, equipment, apparatus, or accessory is selected from the group consisting of a keyboard, a keypad, a stylus pen, a mouse, a handheld device, a remote control, a touch screen, a phone, a handheld device, and a display.

[0214] In one aspect, a personal-care appliance is provided that includes the coating, coating fluid, or spray fluid described above.

[0215] In one aspect of the personal-care product, the coating or spray fluid is water-soluble or water-dispersible.

[0216] In one aspect, a method of disinfecting a surface is provided, comprising applying the composition described above.

[0217] In one aspect, a method of reducing antimicrobial growth on a surface is provided, comprising applying the above-described composition to the surface.

[0218] In one aspect, a method of preventing antimicrobial growth on a surface is provided, comprising applying the above-described composition to the surface.

[0219] In one aspect, a method is provided that includes forming a coating solution containing the composition.

[0220] In one aspect, methods of using the above-described compositions are provided. Using can include, for example, contacting a surface with the composition.

[0221] In one aspect, a method is provided that includes providing any of the antimicrobial coatings, coating fluids, or spray fluids that include the above-described compositions, and applying the antimicrobial coating, coating fluid, or spray fluid to a surface.

[0222] In one aspect, a method is provided that includes directing a coating solution to a surface and providing a coating on the surface through application of the coating solution to the surface.

[0223] In one aspect, a polymer or interpenetrating polymer network comprising: (a) reacting a first multifunctional crosslinker with a first quaternary ammonium salt to form a first adduct; (b) optionally reacting the polyethyleneimine intermediate with a second multifunctional crosslinker to form a second adduct; (c) optionally reacting the first multifunctional crosslinker or the fourth multifunctional crosslinker with a second quaternary ammonium salt to form a third adduct; (d) combining (i) the first adduct, (ii) the polyethyleneimine intermediate or the second adduct, and (iii) the third adduct, if present, with optionally a polyol and optionally a third multifunctional crosslinker to form an oil phase; (e) dissolving a water-soluble polymer in water to form an aqueous phase; (f) combining the oil and water phases to form an oil-in-water emulsion; and (g) applying the emulsion to a surface and allowing the emulsion to dry and cure on the surface to form a polymer or interpenetrating polymer network on the surface.

[0224] In one aspect, the blocking agent is added to the oil phase after step (d) but before step (f).

[0225] In one aspect, step (d) further comprises combining (i) the first adduct, (ii) the polyethyleneimine intermediate or second adduct, and (iii) the third adduct, if present, with an optional polyol, and optionally a third multifunctional crosslinker, in an organic solvent or diluent to form an oil phase.

[0226] In one aspect, step (d) further comprises adding a chain extender to the oil phase, or step (e) further comprises adding a chain extender to the water phase, or a combination thereof.

[0227] In one embodiment, step (e) further comprises adding a surfactant to the aqueous phase.

[0228] In one aspect, step (e) further comprises adding a defoamer or anti-foaming agent to the aqueous phase.

[0229] In one embodiment, step (e) further comprises adding a surfactant and either an antifoaming agent or an anti-foaming agent to the aqueous phase.

[0230] In one aspect, step (f) further comprises performing a direct emulsification process, where the emulsion is formed by vigorous shear and mixing.

[0231] In one aspect, step (f) further comprises performing a direct emulsification process, in which the emulsion is formed by sonication.

[0232] In one embodiment, step (f) further comprises performing a phase inversion emulsification process in which a water-in-oil emulsion is first prepared, followed by phase inversion to form an oil-in-water emulsion.

[0233] In one aspect, the phase inversion is achieved by changing the phase ratio, temperature, surfactant, solvent, or any combination of two or more thereof.

[0234] In another aspect, the present technology provides a personal-care article comprising any of the above-described coatings, coating fluids, or spray fluids. In some embodiments, the coating fluid or spray fluid is water-soluble or water-dispersible.

[0235] Other embodiments are also described and listed herein. DETAILED DESCRIPTION OF THE INVENTION

[0236] 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 may be apparent that the present technology can 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 various levels of detail in order to provide a substantial understanding of the present technology.

[0237] definition For convenience, the meanings of some terms and phrases used in the specification, examples, and appended claims are provided below. Unless otherwise stated or implied from context, the following terms and phrases include the meanings provided below. The definitions are provided to aid 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 expressly stated, 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 apparent discrepancy between the usage of a term in the art and its definition provided herein, the definition provided herein shall control.

[0238] As used in this specification and the appended claims, the singular forms "a," "an," and "the" include plural referents unless the context clearly dictates otherwise. For example, reference to "a cell" includes a combination of two or more cells, and the like.

[0239] As used herein, the term "approximately" or "about" in reference to a value or parameter is generally interpreted as including numerical values ​​that fall within 5%, 10%, 15%, or 20% of that numerical value in either direction (greater or less than) unless otherwise stated or clear from the context (except where such numerical value is less than 0% or greater than 100% of a possible value). Reference to "approximately" or "about" a value or parameter includes (and describes) embodiments that are directed to that value or parameter. For example, a description that refers to "about X" includes a description of "X."

[0240] As used herein, the term "or" means "and / or." When used herein in phrases such as "A and / or B," the term "and / or" is intended to include A and B, A or B, A alone, and B alone. Similarly, when used in phrases such as "A, B, and / or C," the term "and / or" is intended to encompass 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.

[0241] As used herein, the term "comprising" means that other elements may be present in addition to the defined elements presented. The use of "comprising" indicates inclusion, not limitation.

[0242] The term "consisting of" refers to compositions, methods, and their respective components described herein, excluding any element not recited in the description of the embodiment.

[0243] As used herein, the term "consisting essentially of" refers to 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 characteristic(s) of that embodiment of the technology.

[0244] As used herein, "aryl" refers to a carbocyclic (all carbon) ring that is fully aromatized. An "aryl" group can be composed of two or more fused rings (rings that share two adjacent carbon atoms). When an aryl group is a fused ring system, the ring that is connected to the rest of the molecule is fully aromatized. The other ring(s) in the fused ring system may or may not be fully aromatized. Examples of aryl groups include, but are not limited to, radicals of benzene, naphthalene, and azulene.

[0245] As used herein, "alkyl" refers to a hydrocarbon group that is straight- or branched-chain and fully saturated (no double or triple bonds). The alkyl groups of the compounds disclosed herein may contain 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. Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl, t-butyl, amyl, t-amyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl.

[0246] As used herein, "alkoxy" refers to an alkyl group, as defined above, appended to the parent molecular moiety through an oxy group -O-. As used herein, C1-C6 alkoxy refers to an alkoxy group containing 1 to 6 carbon atoms, and C1-C3 alkoxy refers to 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.

[0247] As used herein, "cycloalkyl" refers, in some embodiments, to a group having 3 to 14 carbon atoms (e.g., C3-C 14 cycloalkyl), or 3 to 10 carbon atoms (e.g., C3-C 10 "Cycloalkyl" refers to a monocyclic, bicyclic, or polycyclic hydrocarbon ring system having 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). Cycloalkyl groups can be saturated or characterized by one or more points of unsaturation (i.e., carbon-carbon double and / or triple bonds), provided that the points of unsaturation do not result in an aromatic system. Examples of monocyclic cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexeneyl, cyclohexynyl, cycloheptyl, cyclohepteneyl, cycloheptadieneyl, cyclooctyl, cycloocteneyl, cyclooctadieneyl, and the like. The rings of bicyclic and polycyclic cycloalkyl groups can be fused, bridged, or spirocyclic.

[0248] As used herein, unless otherwise specified, "heteroalkyl" refers to an alkyl group, as defined herein, in which one or more of the constituent carbon atoms is replaced by nitrogen, oxygen, sulfur, or silicon. A representative example of a heteroalkyl group is alkoxy. A heteroalkylene is a divalent heteroalkyl group.

[0249] As used herein, unless otherwise specified, the term "heteroaryl," in some embodiments, refers to a monocyclic or fused bicyclic aromatic group (or ring) having 5 to 14 (i.e., 5-14-membered heteroaryl), or 5 to 10 (i.e., 5-10-membered heteroaryl), or 5 to 6 (i.e., 5-6-membered heteroaryl) members (i.e., ring vertices) and containing 1 to 5, 1 to 4, 1 to 3, 1 to 2, or 1 heteroatom selected from nitrogen (N), oxygen (O), and sulfur (S). A heteroaryl group can be attached to the remainder of the molecule through a carbon atom or a heteroatom of the heteroaryl group, if chemically permissible. Non-limiting examples of heteroaryl groups include pyridyl, pyridazinyl, pyrazinyl, pyrimindinyl, triazinyl, purinyl, thienopyridinyl, thienopyrimidinyl, pyrazolopyrimidinyl, pyrazolopyridinyl, imidazopyridine, isothiazolyl, pyrazolyl, indazolyl, pteridinyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiadiazolyl, pyrrolyl, thiazolyl, furyl, thienyl, and the like.

[0250] The term "heterocycloalkyl," in some embodiments, refers to a non-aromatic monocyclic, bicyclic, or polycyclic cycloalkyl ring having 3 to 14 members (e.g., a 3-14-membered heterocycle), or 3 to 10 members (e.g., a 3-10-membered heterocycle), or 3 to 8 members (e.g., a 3-8-membered heterocycle), or 3 to 6 members (e.g., a 3-6-membered heterocycle), or 5 to 6 members (e.g., a 5-6-membered heterocycle), and having 1 to 5, 1 to 4, 1 to 3, 1 to 2, or 1 heteroatom selected from nitrogen (N), oxygen (O), sulfur (S), and silicon (Si). Heterocycloalkyl groups are 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 result in an aromatic system. The rings of bicyclic and polycyclic heterocycloalkyl groups can be fused, bridged, or spirocyclic. Non-limiting examples of heterocycloalkyl groups include aziridine, oxirane, thiirane, 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, and the like. A heterocycloalkyl group can be attached to the remainder of the molecule through a ring carbon atom or a ring heteroatom, if chemically permissible.

[0251] As used herein, unless otherwise specified, "independently selected" indicates that each of the specified groups is independently selected from the subsequent list of species.

[0252] The terms "statistically significant" or "significantly" refer to statistical significance, generally meaning a difference of two standard deviations (2SD) or greater.

[0253] The terms "reduce," "reduced," "reduction," or "inhibit" are all used herein to mean a statistically significant amount of reduction. In some embodiments, "reduce," "reduction," or "reduce," or "inhibit" typically refers to 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, "reduction" or "inhibition" does not encompass complete inhibition or reduction compared to a reference level. "Complete inhibition" is 100% inhibition compared to a reference level. The decrease may preferably be down to a level that is accepted as within the normal range for an individual without the given disorder.

[0254] The terms "increased," "increase," "enhance," or "activate" are all used herein to mean an increase by a statistically significant amount. In some embodiments, the terms "increased," "increase," "enhance," or "activate" can mean an increase of at least 10% compared to a reference level, e.g., 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 100%, including 100%, or any increase between 10-100% compared to a reference level, or at least about 2-fold, or at least about 3-fold, or at least about 4-fold, or at least about 5-fold, or at least about 10-fold increase compared to a reference level, or any increase between 2-fold and 10-fold or more. In the context of a marker or symptom, an "increase" is a statistically significant increase in such level.

[0255] As used herein, the term "polyisocyanate" generally refers to a family of polyisocyanates containing two or more isocyanate-reactive groups, such as, but not limited to, DESMODUR® N3300 and N100 (made by Covestro Deutschland AG, Leverkusen, Germany), which are aliphatic polyisocyanates based on HDI (hexamethylene diisocyanate) trimer; DESMODUR® Z4470SN (made by Covestro Deutschland AG, Leverkusen, Germany), which is a multifunctional polyisocyanate based on IPDI (isophorone diisocyanate); WANNATE® T-series polyisocyanates, which are toluene diisocyanate (TDI)-based aromatic polyisocyanates; and LUPRANATE® M-series polyisocyanates, which are 4,4-diphenylmethane diisocyanate (MDI)-based aromatic polyisocyanates.

[0256] As used herein, the term "antimicrobial" is generally used to indicate that a composition or coating of a portion of a surface kills at least some level of pathogens. For example, antimicrobial can be used to indicate biocontrol efficacy, a killing level (3 log, or 99.9%) reduction in at least one organism, or a disinfection level (5 log, or 99.999%) reduction in at least one organism, or sterilization (no detectable organisms). Pathogens, or microorganisms, can include any species of bacteria, viruses, fungi, including molds and yeasts, microalgae, or spores. Thus, antimicrobial herein encompasses antiviral, antibacterial, antifungal, and antialgal (e.g., antimicrobal).

[0257] As used herein, the terms “residual antimicrobial,” “residual self-sterilizing,” and “self-decontaminating surface” are used interchangeably to refer to a surface that maintains antimicrobial effectiveness over a specific period of time under certain conditions once the surface is coated with an antimicrobial coating composition and the composition dries on the surface as a thin film. A coated surface may maintain residual antimicrobial effectiveness indefinitely, or the coating may eventually “wear off” and lose its residual antimicrobial effectiveness. An antimicrobial coating composition may function as a contact disinfectant, bacteriostatic material, disinfectant, or sterilant (e.g., as a liquid antimicrobial applied to a contaminated surface) and may have the ability, once dried or cured on a surface, to leave a residual antimicrobial coating on the surface that can continue to inactivate new microorganisms that come into contact with the coated surface. In various embodiments, a coating composition may be antimicrobial until it dries or cures on the surface, but is still referred to as an antimicrobial coating composition due to its ability to produce a residual antimicrobial coating on the surface. An antimicrobial coating composition for use in various embodiments may provide residual antimicrobial effectiveness to a surface, meaning that microorganisms that are subsequently inoculated onto or otherwise come into contact with the coated surface may experience cell death, destruction, or inactivation. The residual antimicrobial effect enabled by the coatings herein is not limited by a particular mechanism of action, and no theory is offered as such. For example, the antimicrobial effect measured on a surface may be the result of intracellular mutation, inhibition of certain cellular processes, rupture of cell walls, or inactivation of undescribed organisms, such as in the case of viruses. Other antimicrobial effects may include inhibiting the reproduction of organisms or inhibiting the ability of organisms to accumulate in biofilms.

[0258] As used herein, the term "antimicrobial coating composition" refers to a chemical composition containing at least one chemical species that is used to produce a residual antimicrobial coating on a surface after the composition has been applied and then dried, allowed to dry, or cured in some manner. The term also refers to a liquid composition that can then be used as a germicidal spray (disinfectant or sanitizer) because the composition can then dry into an antimicrobial coating. The term also extends to include compositions that can be applied sequentially (e.g., above or below) or simultaneously with the application of an antimicrobial coating composition to help bond the residual antimicrobial coating to the surface, improve the durability of the overall coating, and / or provide a catalytic effect or some kind of enhancing or synergistic effect with the residual antimicrobial coating that includes an antimicrobial active agent. For the sake of brevity herein, each of multiple compositions used sequentially or contemporaneously to produce an overall residual antimicrobial coating on a portion of a surface will be referred to as an "antimicrobial coating composition," even if one or more of the compositions used in the coating does not have discernible antimicrobial activity or the active agent is unclear. The antimicrobial coating composition may contain pure, 100% active chemical species or may be a solution or suspension of a single chemical species in a solvent. In other aspects, the composition may contain a complex mixture of chemicals, some of which may undergo chemical reactions (hydrolysis, self-condensation, etc.) within the composition to produce identifiable or indistinguishable reaction products. For example, monomeric species in the antimicrobial coating composition may be partially or fully polymerized or copolymerized to produce polymers, including homopolymers and copolymers, with a distribution of molecular weights, comonomer ratios, or molecular architectures in solution prior to the coating process using the composition. In other embodiments, the chemical components within the antimicrobial coating composition may chemically react, graft, or form interpenetrating networks on a surface or interphase to which the composition is applied, such as while the composition is drying and concentrating on the surface, or while the coating composition is cured by various methods.In various embodiments, the solution containing the polymer distribution may further polymerize or harden, such as to longer chain lengths or to form a polymer network, while the solution is drying on the surface. Antimicrobial coating compositions for use in various embodiments may further include any number and combination of inert excipients, such as, for example, solvents, buffers, acids, alkalis, surfactants, emulsifiers, stabilizers, UV absorbers, thickeners, free radical initiators, fillers, pigments or colorants, catalysts, and the like.

[0259] As used herein, the term "homopolymer" has its conventional meaning in organic chemistry of a molecule having repeating and identical monomeric units. For simplicity, the term homopolymer herein includes each of the smaller oligomers, i.e., dimers, trimers, tetramers, dendrimers, dendrons, etc., unless otherwise specified. For example, a homopolymer distribution herein may include dimers or more, or trimers or more, as indicated. In some cases, the homopolymer chain length distribution may be well-defined and characterized; in other cases, the distribution may not be characterizable at all and may remain unknown. The term copolymer herein includes random copolymers, block copolymers, graft copolymers, interpolymer composites, interpenetrating networks, etc., and blends thereof.

[0260] As used herein, and unless otherwise indicated, the term "wt. %" has its conventional meaning of weight percent (%) of a component in a chemical composition, based on the total weight of the composition "as made." For example, an aqueous composition containing 1 wt. % amine "based on the total weight of the composition" corresponds to a composition containing 99.0 grams of water and 1.0 gram of amine. In a composition, wt. % refers to the weight % of active material, unless otherwise specified. "As made" means that the composition written refers to what was added to a mixing container, not what the mixture may ultimately become after a particular component reacts, such as when the component hydrolyzes or polymerizes.

[0261] Unless otherwise defined herein, scientific and technical terms used in connection with this application shall have the meanings commonly understood by one of ordinary skill in the art to which this disclosure belongs. It is to be understood that the present technology is not limited to the particular methodology, protocols, and reagents described herein, as such may vary. The terminology used herein is for the purpose of describing particular embodiments only and is not intended to limit the scope of the present technology, which is defined solely by the claims. Definitions of common terms in immunology and molecular biology are provided 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 can be seen in.

[0262] Other terms are defined herein within the description of various aspects of the technology.

[0263] antibacterial coating Surfaces that come into direct or indirect contact with humans and animals are exposed to high microbial loads, which has a demonstrable impact on the transmission of disease and infection. The antimicrobial coatings of the present technology can 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, interior and exterior building components such as handrails, fixtures, fixture knobs, pull handles, and grips; kitchens, washrooms, bathrooms, toilets; personal items; telephones, computers; door handles; counters; furniture; walls; ticket machines; and components such as faucet handles in high-touch areas (e.g., building lounges, public payment facilities, and public transportation); and other difficult-to-clean / access areas such as mechanical equipment and HVAC systems. Furthermore, these coatings can be applied to medical devices and accessories, implants, and instruments, laboratory equipment, factories, water purification equipment, hospitals, schools / childcare facilities, airports, restaurants, gyms, and more.

[0264] Bacteria of particular concern include, but are not limited to, Staphylococcus aureus (Staph), Escherichia coli (E. coli), Methicillin-Resistant Staphylococcus aureus (MRSA), and Vancomycin-Resistant Enterococcus faecalis and Enterobacter aerogenes (VRE). Staph is a group of over 30 strains that cause many different types of infections, including skin infections, food poisoning, and blood poisoning. Most strains of E. coli are not harmful but are part of the healthy flora of the human intestine. However, some strains can cause a variety of illnesses, including pneumonia, urinary tract infections, diarrhea, and meningitis. Some strains of E. coli can cause nausea, vomiting, and fever. MRSA is a type of bacteria that causes infections in different parts of the body. Because it is resistant to antibiotics, it is relatively more difficult to treat than most other strains of Staph. It can cause serious skin, bloodstream, lung, or urinary tract infections. VRE is a type of bacteria called Enterococci that, as its name suggests, has developed resistance to many antibiotics, especially vancomycin. These bacteria can cause serious 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.

[0265] 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), which have been demonstrated to have long survival times on many surfaces. For example, a recent study at an airport 15Detection of pathogenic viral nucleic acids indicated viral surface contamination at multiple sites associated with high contact rates, suggesting a potential risk along standard passenger routes on airport premises. These viruses have the potential to cause serious infections, especially in people who are already sick, vulnerable, and / or immunocompromised.

[0266] In the chemical coatings industry, a 99.9% reduction in bacteria or viruses translates to a three-order of magnitude reduction in microbial risk (i.e., 3 logs). However, there are several physical and chemical requirements that an antimicrobial coating must meet to be a fully effective and widely applicable antiviral / antibacterial / antifungal agent and surface coating. These properties include: 1.Highly antibacterial against a broad spectrum of viruses, bacteria, and fungi. 2. Extremely fast-acting, killing over 99.9% of viruses in less than 10 minutes of contact time and bacteria overnight. 3. Long-lasting, maintains at least 98% bacterial or viral killing efficiency after 100 days of storage under ambient conditions or 72 hours of storage at 40°C / 85%RH humidity. 4. Non-toxic and non-allergenic based on recognized standard testing procedures. 5. The material will not leach over time or when exposed to typical liquids used in cleaning. 6. Visibly colorless and transparent as a surface coating. 7. It is easy to apply as a water-based formulation to a wide range of surfaces and materials by painting, spraying, dipping, or other commonly used application methods. 8. A durable surface coating that is resistant to peeling from the surface or visibly degrading upon contact with water, alcohol, and common solvents. 9. Easy and cost effective to produce from readily available materials. 10. They are produced by versatile synthesis, allowing a wide range of chemical variations to fine-tune their properties (i.e., solubility, etc.) for different applications. To the inventor's knowledge, no antimicrobial coating is yet available that meets most or all of these requirements. Many existing antimicrobial coatings tend to deteriorate over time and lose effectiveness with repeated contamination.

[0267] Conventional coating products that claim to provide antibacterial properties include PAINTGUARD / PAINTSHIELD® from Sherwin Williams Company (Cleveland, Ohio), ALESTA® AM and ALESTA® Ralguard from Axalta (Philadelphia, Pennsylvania), and SILVERSAN™ from PPG Industrial Coatings (Pittsburgh, Pennsylvania). However, while these products typically claim to be 99.9% effective, they require at least five hours after application to reach maximum efficacy. Furthermore, existing solutions tend to deteriorate over time, so their activity performance drops below 90% after recontamination (i.e., repeated exposure to pathogens combined with periodic environmental exposure and / or prolonged scrubbing / washing). With only 90% protection, bacteria and germs have the ability to grow and respire, eventually thriving to the point where existing pathogens on the substrate layer persist, thereby reducing the effectiveness of these coatings.

[0268] Antibacterial polymers have been reported for implants containing metals such as silver. 16 However, these suffer from the fact that the embedded antimicrobial agent may leach over time, causing the polymer coating to lose its antimicrobial activity. Furthermore, such formulations are not entirely satisfactory, as they only provide a 3-log reduction, which fails to completely inhibit bacterial regrowth. This lack of effectiveness may possibly be due to the fact that the silver is used in insufficient amounts and / or is unevenly dispersed throughout the composition, resulting in inconsistent and ultimately ineffective distribution of the antimicrobial particles within the composition / coating.

[0269] Park et al. (2006)17 reported antimicrobially active polymers prepared by reacting polyethyleneimine with hydrophobic long-chain hydrocarbon alkylating agents followed by quaternization by methylation. These polymers have antibacterial and antiviral activity as surface coatings, but the coatings are not colorless, durable, or resistant to contact with water and other common solvents with which surfaces may regularly come into contact.

[0270] Many speculate that the antiviral activity of quaternary ammonium polymers is due to interactions between the hydrophobic quaternary ammonium groups and the negatively charged membrane of viruses, causing membrane disruption that inactivates microorganisms such as viruses. Indeed, the active ingredients in many commercially available antiviral surface sprays are low molecular weight quaternary ammonium surfactant-like materials that are postulated to act by this mechanism, but do not form long-lasting, durable surface coatings.

[0271] Researchers have reported acrylic or methacrylic copolymers with quaternary ammonium functional groups that have antibacterial activity. 18、19 However, they do not produce durable water- and solvent-resistant coatings, and some exhibit some degree of toxicity.

[0272] Several researchers have reported antibacterial polyurethane polymers with quaternary ammonium functional groups. 20、21、22 However, these have several drawbacks. Some are water-soluble and therefore not suitable for durable surface coatings. Others have not reported testing of the coating durability or material toxicity. Some are rather tedious to synthesize, requiring somewhat expensive materials and up to four synthetic steps, including amine blocking and deblocking reactions.

[0273] Gao et al. (2007) 23reported the synthesis and antibacterial activity of polymers synthesized by alkylating polyethyleneimine with propyl epoxide and then quaternizing it with benzyl chloride. These polymers were reported to be highly antibacterial with a short contact time of 4 minutes, but they were water-soluble and therefore not suitable for producing durable surface coatings. Furthermore, no viral or toxicity tests were reported for these polymers.

[0274] Although antimicrobial quaternary ammonium compounds and polymers have been known for some time, simple coatings of these materials have not been optically transparent, highly antimicrobial, or durable, and the simple step of cross-linking the coating to achieve durability is insufficient to simultaneously achieve these properties.

[0275] Polymers or interpenetrating polymer networks of the present technology The present technology provides water-based quaternary ammonium polymer structures, and compositions and formulations thereof, that meet substantially all of the requirements listed above.

[0276] In one aspect, provided herein is a polymer or interpenetrating polymer network comprising the random polymerization / crosslinking product of reagents comprising, consisting essentially of, or consisting of (i) a first adduct of a first multifunctional crosslinker and a first quaternary ammonium salt, (ii) a polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second multifunctional crosslinker, and (iii) a water-soluble polymer.

[0277] In another aspect, provided herein is a polymer or interpenetrating polymer network comprising the random polymerization / crosslinking product of reagents comprising, consisting essentially of, or consisting of: (i) a first adduct of a first multifunctional crosslinker and a first quaternary ammonium salt, and (ii) a polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second multifunctional crosslinker.

[0278] In another aspect, provided herein is a polymer or interpenetrating polymer network comprising the random polymerization / crosslinking product of reagents comprising, consisting essentially of, or consisting of: (i) a first adduct of a first multifunctional crosslinker and a first quaternary ammonium salt; (ii) optionally a polyol; (iii) a polyethyleneimine intermediate or a second adduct of a polyethyleneimine intermediate and a second multifunctional crosslinker; (iv) optionally a third multifunctional crosslinker; and (v) a water-soluble polymer.

[0279] The water-soluble polymer comprises, consists essentially of, or consists of hydroxyethyl cellulose, hydroxypropyl cellulose, methyl cellulose, hydrophobically modified 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), polyethyleneimine, polyacrylamide, or modified polymers or copolymers thereof on the side chains or backbone (e.g., modification(s) that provide reactive functionality, 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 poly(glycidyl methacrylate).

[0280] The water-soluble polymer can be present in the dry polymer or interpenetrating polymer network in an amount of about 0.5% to about 15% by weight, including about 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, or 15% by weight, 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 about 0.5% to about 15%, about 3% to about 12%, or about 5% to about 10% by weight.

[0281] In another aspect, provided herein is a polymer or interpenetrating polymer network comprising the random polymerization / crosslinking product of reagents comprising, consisting essentially of, or consisting of: (i) a first adduct of a first multifunctional crosslinker and a first quaternary ammonium salt; (ii) optionally a polyol; (iii) a polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second multifunctional crosslinker; and (iv) optionally a third multifunctional crosslinker.

[0282] The first quaternary ammonium salt may have the following chemical structure: [ka] During the ceremony, R 1 is -(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 -(CRp R q ) y10 -H, and -(CR m R n ) x11 -W 11 -(CR p R q ) y11 H—, —(C8-C 30 heteroalkyl), -(C8-C 30 Heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Aryl)-(C8-C 30 heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si; R 2 is -(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, -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 (aryl)-(C1-C4 heteroalkyl) has 1 to 2 heteroatoms independently selected from O, S, and Si; R 3 is -(C1-C 30 alkyl), -(C1-C 30 heteroalkyl), -(C1-C 30Heteroalkyl)-(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, -(C1-C 30 heteroalkyl), -(C1-C 30 Heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Aryl)-(C1-C 30 heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si; A is -(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 -(C3-C 20 Heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; -(C3-C 20alkylene)- and -(C3-C 20 Heteroalkylene)- is -(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 is 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 5- to 6-membered cycloalkyl, C-C 10 selected from aryl, 5- to 6-membered heterocycloalkyl, and 5- to 6-membered heteroaryl, wherein heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si; x10 is an integer from 1 to 30, y10 is an integer from 0 to 29, and 8≦(x10+y10)≦30; x11 is an integer of 1 to 30, y11 is an integer of 0 to 29, and 8≦(x11+y11)≦30; x20 is an integer of 1 to 4, y20 is an integer of 0 to 3, and x20+y20≦4; x21 is an integer of 1 to 4, y21 is an integer of 0 to 3, and x21+y21≦4; x30 is an integer from 1 to 30, y30 is an integer from 0 to 29, and x30+y30≦30; x31 is an integer of 1 to 30, y31 is an integer of 0 to 29, and x31+y31≦30; x40 is an integer from 1 to 19, y40 is an integer from 1 to 19, and 3≦(x40+y40)≦20; x41 is an integer from 1 to 20, y41 is an integer from 0 to 19, and 3≦(x41+y41)≦20; Y is -OH, -NHR 4 , -SH, -COH, -C(O)NHR 4 , -C(S)NHR 4 , [ka] is selected from the group consisting of Each R 4 are independently 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), -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si; X - is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, borate, or an organically substituted derivative of any of the foregoing.

[0283] In some embodiments, R 1 is -(C 12 -C 30alkyl), -(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), -(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. In some embodiments, R 1 is -(C 12 -C 30 In some embodiments, R 1 has 1 to 4 heteroatoms independently selected from O, S, and Si; 30 In some embodiments, R 1 is -(C6-C 10 Aryl)-(C 12 -C 30 In some embodiments, R 1 is -(C 12 -C 30 Alkyl)-(C6-C 10 aryl). In some embodiments, R 1 has 1 to 4 heteroatoms independently selected from O, S, and Si; 10 Aryl)-(C 12 -C 30 In some embodiments, R1 has 1 to 4 heteroatoms independently selected from O, S, and Si; 12 -C 30 Heteroalkyl)-(C6-C 10 aryl). In some embodiments, R 1 is -(CR m R n ) x10 -W 10 -(CR p R q ) y10 In some embodiments, R 1 is -(CR m R n ) x11 -W 11 -(CR p R q ) y11 -H.

[0284] 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 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 has 1 to 4 heteroatoms independently selected from O, S, and Si; 10 In some embodiments, R 2 is -(C1-C4 heteroalkyl)-(C6-C 10 aryl). In some embodiments, R 2 is -(CR m Rn ) x20 -W 20 -(CR p R q ) y20 In some embodiments, R 2 is -(CR m R n ) x21 -W 21 -(CR p R q ) y21 -H.

[0285] In some embodiments, R 3 is -(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), -(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. 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 In some embodiments, R 3 is -(C1-C4 alkyl)-(C6-C 10 aryl). In some embodiments, R 3 has 1 to 4 heteroatoms independently selected from O, S, and Si; 10In some embodiments, R 3 is -(C1-C4 heteroalkyl)-(C6-C 10 aryl). In some embodiments, R 3 is -(CR m R n ) x30 -W 30 -(CR p R q ) y30 In some embodiments, R 3 is -(CR m R n ) x31 -W 31 -(CR p R q ) y31 -H.

[0286] In some embodiments, R 2 and R 3 is methyl. In some embodiments, R 1 is C 12 -C 30 alkyl, and R 2 and R 3 is methyl.

[0287] In some embodiments, A is -(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 -(C3-C4) optionally substituted with 1 to 6 substituents independently selected from -(C3-C4) 20 In some embodiments, A has 1 to 4 heteroatoms independently selected from O, S, and Si, and is -(C-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 -(C3-C aryl) optionally substituted with 1 to 6 substituents independently selected from 20 In some embodiments, A is -(C6-C 10 Arylene)-(C3-C 20 In some embodiments, A is -(C-C alkylene). 20 Alkylene)-(C6-C 10 arylene)-.

[0288] In some embodiments, A is -(CR m R n ) x40 -W 40 -(CR p R q ) y40 In some embodiments, A is -(CR m R n ) x41 -W 41 -(CR p R q ) y41 -It is.

[0289] In some embodiments, A is —(CH) m -or-(CH2CHR 5 -O-) n CH2CHR 5 wherein m is an integer from 2 to 20, n is 0, 1, 2, 3, 4, or 5, and each R 5 are independently 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 10aryl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 5 is H or methyl.

[0290] In some embodiments, Y is -OH. In some embodiments, Y is -NHR 4 In some embodiments, Y is -SH. In some embodiments, Y is -COH. In some embodiments, Y is -C(O)NHR 4 where R 4 is 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), -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) 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 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), -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C10 aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, Y is [ka] where each R 4 is 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), -(C-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, Y is [ka] where each R 4 is 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), -(C-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si.

[0291] X -can be independently selected from the group consisting of acetate, halide (e.g., chloride, bromide, or iodide), sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof. As used herein, and unless otherwise specified, "organically substituted derivative" refers to an anion in which the sulfur atom, phosphorus atom, boron atom, silicon atom, or carbonyl group is replaced with either an alkyl group or an aryl group. Non-limiting examples include methyl sulfate, methanesulfonate, p-toluenesulfonate, trifluoromethylsulfonate, and trifluoroacetate.

[0292] In some embodiments, the first quaternary ammonium salt is [ka] Or a combination of two or more of them.

[0293] The first quaternary ammonium salt can be present in the dry polymer or interpenetrating polymer network in an amount of about 1% to about 50% by weight, including 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% by weight, 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% to about 25% by weight. More precisely, the amount of quaternary ammonium salt may be expressed in millinormals per gram (mN / g) instead of weight percent based on the total weight of the dry polymer or interpenetrating polymer network. The first quaternary ammonium salt may 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, including 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 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.

[0294] The first multifunctional crosslinker can be a first polyisocyanate. In some embodiments, the first polyisocyanate has an average isocyanate functionality of 2 to 5, including an average isocyanate functionality of 2, 3, 4, or 5. In some embodiments, the first polyisocyanate has an average isocyanate functionality of 3 to 4.

[0295] The second multifunctional crosslinker can be a second polyisocyanate. In some embodiments, the second polyisocyanate has an average isocyanate functionality of 2 to 5, including an average isocyanate functionality of 2, 3, 4, or 5. In some embodiments, the second polyisocyanate has an average isocyanate functionality of 3 to 4.

[0296] The third multifunctional crosslinker can be a third polyisocyanate. In some embodiments, the third polyisocyanate has an average isocyanate functionality of 2 to 5, including an average isocyanate functionality of 2, 3, 4, or 5. In some embodiments, the third polyisocyanate has an average isocyanate functionality of 3 to 4.

[0297] In some embodiments, the first multifunctional crosslinker is a first polyisocyanate, the second multifunctional crosslinker, if present, is a second polyisocyanate, and the third multifunctional crosslinker, if present, is a third polyisocyanate, and the first polyisocyanate, second polyisocyanate, and third polyisocyanate are different. In some embodiments, the first multifunctional crosslinker is a first polyisocyanate, the second multifunctional crosslinker, if present, is a second polyisocyanate, and the third multifunctional crosslinker, if present, is a third polyisocyanate, and the first polyisocyanate, second polyisocyanate, and third polyisocyanate are the same.

[0298] Each of the first, second, and third polyisocyanates 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), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

[0299] In some embodiments, each of the first, second, and third polyisocyanates is independently selected from the group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T-series polyisocyanates, and LUPRANATE® M-series polyisocyanates. DESMODUR® N-3300 and DESMODUR® N-100 are aliphatic polyisocyanates based on HDI (hexamethylene diisocyanate) trimer. DESMODUR® Z4470SN is a multifunctional polyisocyanate based on IPDI (isophorone diisocyanate). WANNATE® T-series polyisocyanates are aromatic polyisocyanates based on toluene diisocyanate (TDI). LUPRANATE® M series polyisocyanates are aromatic polyisocyanates based on 4,4-diphenylmethane diisocyanate (MDI).

[0300] The first multifunctional crosslinker can be present in the dry polymer or interpenetrating polymer network in an amount of about 2% to about 25% by weight, including 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% by weight, or any value therebetween. In some embodiments, the first multifunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of about 7% to about 15% by weight, or about 5% to about 20% by weight.

[0301] The second multifunctional crosslinker can be present in the dry polymer or interpenetrating polymer network in an amount of about 0.1% to about 10% by weight, including 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% by weight, or any value therebetween. In some embodiments, the second multifunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of about 1% to about 10%, about 2% to about 8%, or about 3% to about 6% by weight.

[0302] The third multifunctional crosslinker may be present in the dry polymer or interpenetrating polymer network in an amount of about 0.1 wt % to about 20 wt %, including 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, or 20 wt %, or any value therebetween. In some embodiments, the third multifunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of from about 1% to about 20% by weight, or from about 2% to about 15% by weight.

[0303] In some embodiments, the first adduct has an average isocyanate functionality of 2 to 3. In some embodiments, the first adduct has an average isocyanate functionality of about 2.05 to about 2.3.

[0304] The first adduct can be present in the dry polymer or interpenetrating polymer network in an amount of about 5% to about 70% by weight, including 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% by weight, or any value therebetween. In some embodiments, the first adduct is present in the dry polymer or interpenetrating polymer network in an amount of about 10% to about 50% by weight, about 15% to about 65% by weight, about 15% to about 60% by weight, about 15% to about 50% by weight, about 20% to about 70% by weight, about 20% to about 60% by weight, or about 20% to about 50% by weight.

[0305] The polyol can be present in the dry polymer or interpenetrating polymer network in an amount of about 1% to about 40% by weight, including 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% by weight, or any value therebetween. In some embodiments, the polyol is present in the dry polymer or interpenetrating polymer network in an amount of about 5% to about 25% by weight.

[0306] 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.

[0307] In some embodiments, the polyol comprises, consists essentially of, or consists of polytetramethylene glycol (PTMG), polyethylene glycol (PEG), polypropylene glycol (PPG), or a combination 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).

[0308] In some embodiments, the polyol comprises, consists essentially of, or consists of a polyether polyol, a polyester polyol, or a combination thereof.

[0309] The polyol can have an average molecular weight of about 300 to about 3000 daltons, including about 200, 250, 300, 350, 400, 450, 500, 550, 600, 650, 700, 750, 800, 850, 900, 950, 1000, 1050, 1100, 1150, 1200, 1250, 1300, 1350, 1400, 1450, 1500, 1550, 1600, 1650, 1700, 1750, 1800, 1850, 1900, 1950, or 2000 daltons, or any value therebetween. In some embodiments, the polyol has an average molecular weight of about 400 to about 2000, or about 600 to about 1500 daltons.

[0310] In some embodiments, the polyol is pre-reacted with a first polyisocyanate to form an isocyanate-endcapped prepolymer. In some embodiments, the polyol is pre-reacted with a third polyisocyanate to form an isocyanate-endcapped prepolymer.

[0311] In some embodiments, the polyethyleneimine intermediate comprises an optionally substituted hydroxyalkylene functional group that reacts with the first adduct and, if present, the second multifunctional crosslinker. In some embodiments, the polyethyleneimine intermediate comprises an optionally substituted hydroxyalkylene functional group that reacts with the first adduct and, if present, the second multifunctional crosslinker, and, if present, the third multifunctional crosslinker.

[0312] In some embodiments, the hydroxyalkylene functional group is —N + (R 20 )3X - , -(C6-C 10 aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy; and each R 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl, and each X - is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof. In some embodiments, the hydroxyalkylene functional group is -N + (R 20 )3X -and each R is substituted with C1-C6 alkyl substituted with 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl, and each X - are independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof. In some embodiments, the hydroxyalkylene functional group is (CH)-N + (Me)3Cl - In some embodiments, the hydroxyalkylene functional group is hydroxyethylene, hydroxypropylene, hydroxybutylene, or oligomers thereof.

[0313] In some embodiments, the polyethyleneimine intermediate comprises the reaction product of a reagent comprising polyethyleneimine, a monoepoxide, and an alkylating agent, wherein the monoepoxide is —(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with hydroxy, C1-C6 alkoxy, C6-C6 optionally substituted with C1-C6 alkyl 10 Optionally substituted with C1-C6 alkyl optionally substituted with a substituent selected from aryl, and carboxy.

[0314] 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.

[0315] In some embodiments, the polyethyleneimine intermediate comprises the reaction product of a polyethyleneimine, a monoepoxide, and optionally a reagent comprising an alkylating agent, wherein the monoepoxide is -(C1-C6 alkyl)-N + (R 20 )3X - and each R 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl, and each X - is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

[0316] In some embodiments, the polyethyleneimine intermediate comprises the reaction product of polyethyleneimine and a reagent comprising a monoepoxide, wherein the monoepoxide is —(C1-C6 alkyl)-N + (R 20 )3X -and each R 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl, and each X - is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

[0317] In some embodiments, the alkylating agent is one or more R 21 -LG, wherein each R 21 are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 and —(C-C alkyl) optionally substituted with a substituent selected from —(aryl), and —(C-C alkoxy) optionally substituted with —OH, and each LG is a leaving group. As used herein, and unless otherwise indicated, a leaving group may be a halide, sulfonate, or the like. In some embodiments, the alkylating agent is a benzyl halide or a hexyl halide.

[0318] In some embodiments, the polyethyleneimine intermediate comprises the reaction product of a polyethyleneimine and a reagent comprising a haloalkanol. In some embodiments, the haloalkanol is X 30 -(C2-C6 alkylene)-OH, wherein X 30 is Cl, Br, or I.

[0319] In some embodiments, the reagent for the reaction product comprising the polyethyleneimine intermediate further comprises a monoisocyanate. In some embodiments, the monoisocyanate comprises one or more R 30 -NCO, wherein each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 alkyl, and (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, 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. In some embodiments, the monoisocyanate comprises octyl isocyanate, octadecyl isocyanate, or a combination thereof.

[0320] The polyethyleneimine intermediate may be present in the dry polymer or interpenetrating polymer network in an amount of about 0.1% to about 50% by weight, which may be 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, 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, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 9 In some embodiments, the polyethyleneimine intermediate is present in the dry polymer or interpenetrating polymer network in an amount of about 3% to about 30% by weight.

[0321] In some embodiments, at least 20% of the nitrogen atoms of the polyethyleneimine intermediate are quaternized. In some embodiments, at least 30% of the nitrogen atoms of the polyethyleneimine intermediate are quaternized.

[0322] The polyethyleneimine can have a molecular weight of about 300 to about 270,000 daltons, including about 300, 400, 500, 600, 700, 800, 900, 1000, 2500, 5000, 10,000, 25,000, 50,000, 75,000, 100,000, 125,000, 150,000, 175,000, 200,000, 225,000, 250,000, or 270,000 daltons, or any value therebetween. In some embodiments, the polyethyleneimine has a molecular weight of about 10,000 to about 200,000 daltons, or about 25,000 to about 120,000 daltons.

[0323] In some embodiments, the polyethyleneimine is branched. In some embodiments, the polyethyleneimine is hyperbranched.

[0324] In some embodiments, the polyethyleneimine has a ratio of primary to secondary to tertiary amines of about 1:2:1 to about 1:1:1. In some embodiments, the polyethyleneimine has a ratio of primary to secondary to tertiary amines of about 1:1:0.7.

[0325] In some embodiments, the polyethyleneimine intermediate is [ka] or a copolymer of any two or more thereof, wherein: Each Y 3 are independently H or -OY 2 and for all Y 3 But it cannot be H, Each Y 2 are independently H or -C(O)-NHR 30 and for all Y 2 -C(O)-NHR 30 It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 are independently hydrogen; -N(R 20 )3, -(C6-C 10 aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy; 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl; Each R 21 are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 C1-C6 alkyl optionally substituted with a substituent selected from -(aryl), and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 alkyl, and (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, 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 X - are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and organically substituted derivatives thereof; however, R 10 But -(C6-C10 aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy, the polyethyleneimine intermediate is [ka] The condition is that the item is selected from the following:

[0326] In some embodiments, the polyethyleneimine intermediate is [ka] wherein each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000.

[0327] In some embodiments, the second adduct is of formula (I): [ka] During the ceremony, Each A is independently [ka] or a copolymer of any two or more thereof, wherein the attachment of each A forms a carbamate linkage; Each Y 3 are independently H or -OY 2 and for all Y 3 But it cannot be H, Each Y 2 are independently H or -C(O)-NHR 30 and for all Y 2 -C(O)-NHR 30 It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 are independently hydrogen; -N(R 20 )3, -(C6-C 10 aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy; 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl; Each R 21 are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 C1-C6 alkyl optionally substituted with a substituent selected from -(aryl), and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 Alkyl, (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b)(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, and (3) [ka] 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 are independently -(C-C optionally substituted with phenyl) 10 alkylene)- or a 3- to 8-membered cycloalkyl ring; each X - are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and organically substituted derivatives thereof; however, R 10 But -(C6-C 10 aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy, each A is independently [ka] The condition is that the item is selected from the following:

[0328] In some embodiments, the second adduct is of formula (II): [ka] During the ceremony, Each A is independently [ka] or a copolymer of any two or more thereof, wherein the attachment of each A forms a carbamate linkage; Each Y 3 are independently H or -OY 2 and for all Y 3 But it cannot be H, Each Y 2 are independently H or -C(O)-NHR 30 and for all Y 2 -C(O)-NHR 30 It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 are independently hydrogen; -N(R 20 )3, -(C6-C 10 aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy; 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl; Each R 21 are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 C1-C6 alkyl optionally substituted with a substituent selected from -(aryl), and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 Alkyl, (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, and (3) [ka] 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 are independently -(C-C optionally substituted with phenyl) 10 alkylene)- or a 3- to 8-membered cycloalkyl ring; each X - are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and organically substituted derivatives thereof; however, R 10 But -(C6-C 10aryl), and -(C-C alkoxy) optionally substituted with -OH, -(C-C alkoxy), -(C-C alkyl) optionally substituted with -(C-C 10 aryl), and carboxy, each A is independently [ka] The condition is that the item is selected from the following:

[0329] In some embodiments, the second adduct is present in the dry polymer or interpenetrating polymer network in an amount of about 1% to about 30% by weight, including 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% by weight, 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% to about 15% by weight.

[0330] The reagents for the random polymerization / crosslinking product include (i) a first multifunctional crosslinker or a fourth multifunctional crosslinker and (ii) a second quaternary ammonium salt. [ka] wherein: R 1a , R 2a , and R 3a are each independently methyl or ethyl; A 1 is -(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 Rq1 ) y42 -, and -(CR m1 R n1 ) x43 -W 43 -(CR p1 R q1 ) y43 -(C3-C 20 Heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; -(C3-C 20 alkylene)- and -(C3-C 20 Heteroalkylene)- is -(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 is selected from —C(O)—, —C(O)O—, —OC(O)—, —C(O)NH—, and —NHC(O)—; W 43 is a 5- to 6-membered cycloalkyl, C6-C 10 selected from aryl, 5- to 6-membered heterocycloalkyl, and 5- to 6-membered heteroaryl, wherein heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si; x42 is an integer from 1 to 19, y42 is an integer from 1 to 19, and 3≦(x42+y42)≦20; x43 is an integer from 1 to 20, y43 is an integer from 0 to 19, and 3≦(x43+y43)≦20; Y1 -OH, -NHR 4a , -SH, -COH, -C(O)NHR 4a , -C(S)NHR 4a , [ka] is selected from the group consisting of Each R 4a are independently H, (C-(C-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), -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si; X - is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, borate, or an organically substituted derivative of any of the foregoing.

[0331] The fourth multifunctional crosslinker can be present in the dry polymer or interpenetrating polymer network in an amount of about 0.1 wt% to about 15 wt%, including 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, 11, 12, 13, 14, or 15 wt%, or any value therebetween. In some embodiments, the fourth multifunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of about 2 wt% to about 8 wt%.

[0332] The fourth multifunctional crosslinker can be different from the first multifunctional crosslinker, and, if present, the second multifunctional crosslinker, and, if present, the third multifunctional crosslinker.

[0333] In some embodiments, the fourth multifunctional crosslinker 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-cyclohexylisocyanate) (H12MDI), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI). In some embodiments, the fourth polyisocyanate is selected from the group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T-series polyisocyanates, and LUPRANATE® M-series polyisocyanates.

[0334] In some embodiments, the second quaternary ammonium salt is [ka] is.

[0335] The second quaternary ammonium salt can be present in the dry polymer or interpenetrating polymer network in an amount of about 1% to about 15% by weight, including about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15% by weight, or any value therebetween. In some embodiments, the second quaternary ammonium salt is present in the dry polymer or interpenetrating polymer network in an amount of about 3% to about 10% by weight.

[0336] In some embodiments, the third adduct has an average isocyanate functionality of 2 to 3. In some embodiments, the third adduct has an average isocyanate functionality of 2.05 to about 2.3.

[0337] The third adduct can be present in the dry polymer or interpenetrating polymer network in an amount of about 2% to about 30% by weight, including 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% by weight, or any value therebetween. In some embodiments, the second quaternary ammonium salt is present in the dry polymer or interpenetrating polymer network in an amount of about 3% to about 20% by weight.

[0338] The reagent for random polymerization / crosslinking products is 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 propanediol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexanedimethanol, or a combination of two or more thereof. The chain extender may be present in the dry polymer or interpenetrating polymer network in an amount of about 0.5% to about 10% by weight, including about 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10% by weight, or any value therebetween. In some embodiments, the chain extender may be present in the dry polymer or interpenetrating polymer network in an amount of about 1% to about 5% by weight.

[0339] In another aspect, provided herein is a polymer or interpenetrating polymer network comprising the random polymerization / crosslinking product of reagents comprising, consisting essentially of, or consisting of: (i) a first adduct of a first multifunctional crosslinker and a first quaternary ammonium salt; (ii) optionally a polyol; (iii) a polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second multifunctional crosslinker; (iv) optionally a third multifunctional crosslinker; (v) optionally a third adduct of (a) the first multifunctional crosslinker or a fourth multifunctional crosslinker and (b) a second quaternary ammonium salt; (vi) optionally a chain extender; and (vii) a water-soluble polymer.

[0340] In another aspect, provided herein is a polymer or interpenetrating polymer network comprising the random polymerization / crosslinking product of reagents comprising, consisting essentially of, or consisting of: (i) a first adduct of a first multifunctional crosslinker and a first quaternary ammonium salt; (ii) optionally a polyol; (iii) a polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second multifunctional crosslinker; (iv) optionally a third multifunctional crosslinker; (v) optionally, a random polymerization / crosslinking product of reagents comprising, consisting essentially of, or consisting of: (a) a first multifunctional crosslinker or a fourth multifunctional crosslinker and (b) a third adduct of a second quaternary ammonium salt; and (vi) optionally a chain extender.

[0341] In some embodiments, a first quaternary ammonium salt reacts with a first polyisocyanate to form a first adduct, which 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, for example, to urethane or urea, by reaction with the first quaternary ammonium salt. The unreacted isocyanate functional groups are then reacted with one or more of a polyol (if present), a chain extender (if present), a polyethyleneimine intermediate or second adduct, water, and a water-soluble polymer (if reactive). Similarly, in some embodiments, a second quaternary ammonium salt reacts with the first polyisocyanate or a fourth polyisocyanate to form a third adduct, which retains unreacted isocyanate functional groups from the first or fourth polyisocyanate. In some embodiments, about 10% to about 40%, preferably about 25% to 33%, of the isocyanate functional groups on the first or fourth polyisocyanate are converted, for example, to urethanes or ureas by reaction with the second quaternary ammonium salt. If present, the third multifunctional crosslinker and / or third adduct may also react with one or more of the polyol (if present), chain extender (if present), polyethyleneimine intermediate or second adduct, water, and water-soluble polymer (if reactive). The first adduct and third adduct are preformed before interacting with the polyol (if present), chain extender (if present), polyethyleneimine intermediate or second adduct, and water-soluble polymer (if reactive).

[0342] In another aspect, the polymer or interpenetrating polymer network is (a) reacting a first multifunctional crosslinker with a first quaternary ammonium salt to form a first adduct; (b) optionally reacting the polyethyleneimine intermediate with a second multifunctional crosslinker to form a second adduct; (c) optionally reacting the first multifunctional crosslinker or the fourth multifunctional crosslinker with a second quaternary ammonium salt to form a third adduct; (d) combining (i) the first adduct, (ii) the polyethyleneimine intermediate or the second adduct, and (iii) the third adduct, if present, with optionally a polyol and optionally a third multifunctional crosslinker to form an oil phase; (e) dissolving a water-soluble polymer in water to form an aqueous phase; (f) combining the oil and water phases to form an oil-in-water emulsion; and (g) Prepared by applying the emulsion to a surface and allowing the emulsion to dry and cure on the surface to form a polymer or interpenetrating polymer network on the surface.

[0343] In some embodiments, the blocking agent is added to the oil phase after step (d) but before step (f).

[0344] In some embodiments, step (d) further comprises combining (i) the first adduct, (ii) the polyethyleneimine intermediate or second adduct, and (iii) the third adduct, if present, with optionally a polyol, and optionally a second multifunctional crosslinker, in an organic solvent or diluent to form an oil phase.

[0345] 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.

[0346] In some embodiments, step (e) further comprises adding a surfactant to the aqueous phase. In some embodiments, step (e) further comprises adding a defoamer or anti-foaming agent to the aqueous phase. In some embodiments, step (e) further comprises adding either a surfactant and a defoamer or anti-foaming agent to the aqueous phase.

[0347] In some embodiments, step (f) further comprises performing a direct emulsification process, in which the emulsion is formed by vigorous shear and mixing. In some embodiments, step (f) further comprises performing a direct emulsification process, in which the emulsion is formed by sonication.

[0348] In some embodiments, step (f) further comprises performing a phase inversion emulsification process in which a water-in-oil emulsion is first prepared, followed by phase inversion to form an oil-in-water emulsion. Phase inversion can be achieved, for example, by changing the phase ratio, temperature, surfactant, solvent, or any combination of two or more thereof.

[0349] In some embodiments, a multiple phase water-in-oil-in-water emulsion is formed prior to conversion to an oil-in-water emulsion in step (f).

[0350] In some embodiments, combining the oil phase and the aqueous phase in step (f) forms a combination of an oil-in-water emulsion and a multiple water-in-oil-in-water emulsion.

[0351] In another aspect, the reagents for preparing the polymers or interpenetrating polymer networks described herein are included in an antimicrobial composition.

[0352] Thus, in another aspect, there is provided an antimicrobial composition comprising an oil-in-water emulsion, the oil-in-water emulsion comprising: (i) an oil phase, a first adduct of a first multifunctional crosslinker and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first multifunctional crosslinker; optionally a polyol, a polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second multifunctional crosslinker; and an oil phase optionally comprising a third multifunctional crosslinker; (ii) an aqueous phase comprising a water-soluble polymer. The composition may be applied to a surface and allowed to dry and cure, thereby forming the polymer or interpenetrating polymer network of the present technology.

[0353] The reactive linking group of the first quaternary ammonium salt is -OH, -NHR 4 , -SH, -COH, -C(O)NHR 4 , -C(S)NHR 4 , [ka] wherein each R 4 are independently 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), -(C6-C 10 aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si.

[0354] The first quaternary ammonium salt described herein and incorporated into the first adduct may be present in the oil phase in an amount of about 1% to about 50% by weight, based on the dry weight of the oil phase. As used herein, and unless otherwise indicated, "dry weight of the oil phase" refers to the weight of the oil phase in the absence of any organic solvent 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, the first quaternary ammonium salt incorporated in the first adduct is present in the oil phase in an amount of from about 1% to about 25% by weight, or from about 5% to about 25% by weight, based on the dry weight of the oil phase.

[0355] The first multifunctional crosslinker (e.g., first polyisocyanate) described herein and incorporated into the first adduct can be present in the oil phase in an amount of about 2% to about 25% by weight, based on the dry weight of the oil phase, including 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, the first multifunctional crosslinker (e.g., first polyisocyanate) incorporated into the first adduct is present in the oil phase in an amount of about 5% to about 20% by weight, based on the dry weight of the oil phase.

[0356] The first adduct described herein may be present in the oil phase in an amount of about 5% to about 70% by weight based on the dry weight of the oil phase, which may be 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%, 70%, 71%, 72%, 73%, 74%, 75%, 76%, 77%, 78%, 79%, 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, 100%, 101%, 102%, 103%, 104%, 105%, 106%, 107%, 108%, 109%, 110%, 111%, 112%, 113%, 114%, 115%, 116%, 117%, 11 In some embodiments, the first adduct is present in the oil phase in an amount of about 10% to about 50% by weight, about 15% to about 65% by weight, about 15% to about 60% by weight, about 15% to about 50% by weight, about 20% to about 70% by weight, about 20% to about 60% by weight, or about 20% to about 50% by weight, based on the dry weight of the oil phase.

[0357] The polyethyleneimine intermediates described herein may be 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, including 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%, 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%, 70%, 71%, 72%, 73%, 74%, 75%, 76%, 77%, 78%, 79%, 80%, 81%, 82%, 83%, 84%, 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92 %, 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, the polyethyleneimine intermediate is present in the oil phase in an amount of about 3% to about 30% by weight based on the dry weight of the oil phase.

[0358] The second multifunctional crosslinker (e.g., second polyisocyanate) described herein and incorporated into the second adduct can be present in the oil phase in an amount of about 0.1% to about 10% by weight, based on the dry weight of the oil phase, including 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, the second multifunctional crosslinker (e.g., second polyisocyanate) is present in the oil phase in an amount of about 2% to about 8% by weight, or about 3% to about 6% by weight, based on the dry weight of the oil phase.

[0359] The second adduct described herein may be present in the oil phase in an amount of about 1% to about 30% by weight based on the dry weight of the oil phase, including 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, the second adduct is present in the oil phase in an amount of about 3% to about 15% by weight based on the dry weight of the oil phase.

[0360] In some embodiments, the oil phase further comprises a third multifunctional crosslinker, as described herein. The third multifunctional crosslinker (e.g., a third polyisocyanate) may be present in the oil phase in an amount of about 5% to about 25% by weight, based on the dry weight of the oil phase. 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, the third multifunctional crosslinker (e.g., a third polyisocyanate) is present in the oil phase in an amount of about 5% to about 20% by weight, based on the dry weight of the oil phase.

[0361] In some embodiments, the oil phase further comprises a third additive described herein. The third additive may be present in the oil phase in an amount of about 2% to about 30% by weight based on the dry weight of the oil phase, including 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, the third additive is present in the oil phase in an amount of about 3% to about 20% by weight based on the dry weight of the oil phase.

[0362] In some embodiments, the second quaternary ammonium salt described herein and incorporated into the third adduct is present in the oil phase in an amount of about 1% to about 15% by weight based on the dry weight of the oil phase, including about 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, or 15%, or any value therebetween. In some embodiments, the second quaternary ammonium salt described herein and incorporated into the third adduct is present in the oil phase in an amount of about 3% to about 10% by weight based on the dry weight of the oil phase.

[0363] The fourth multifunctional crosslinker (e.g., fourth polyisocyanate) described herein and incorporated into the third adduct can be present in the oil phase in an amount of about 0.1% to about 15% by weight based on the dry weight of the oil phase, including 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, the fourth multifunctional crosslinker (e.g., fourth polyisocyanate) described herein and incorporated into the third adduct is present in the oil phase in an amount of about 2% to about 8% by weight based on the dry weight of the oil phase.

[0364] In some embodiments, the reactive isocyanate functional groups on the first adduct and / or the third adduct are blocked with a blocking agent. Reaction with the blocking agent converts the reactive isocyanate functional groups to blocked isocyanates (i.e., the isocyanate groups are reversibly protected from immediate reaction with nucleophiles). This slows the rate of the polyisocyanate reaction with water in the subsequent emulsification step and / or the crosslinking reaction with, for example, any polyol(s) in the oil phase and / or a water-soluble polymer (such as hydroxyethyl cellulose) in the aqueous phase. In some embodiments, there is a significant improvement in the reproducibility of the rheological properties, particle size, and distribution of the resulting emulsion. 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 yield of the coated product is improved. In some embodiments, no blocking agent is used to provide a faster-curing coating.

[0365] In some embodiments, the blocking agent is selected from the group consisting of oximes, phenols, malonates, alcohols, lactams, dicarbonyl compounds, hydroxamates, bisulfite adducts, hydroxylamines, esters of p-hydroxybenzoic acid and salicylic acid, hi 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.

[0366] In some embodiments, the composition further comprises a deblocking agent. Deblocking agents include, but are not limited to, organotin, organobismuth, and tert-amines. Non-limiting examples include triethanolamine, N,N,N'N'-tetrakis(2-hydroxyethyl)ethylenediamine, and K-KAT XK-651 (bismuth carboxylate catalyst).

[0367] In some embodiments, the oil phase comprises HO—(Cn 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 propanediol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexanedimethanol, or a combination of two or more thereof. The chain extender may be present in the oil phase in an amount of up to about 10% by weight, based on the dry weight of the oil phase, including about 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or any value therebetween. In some embodiments, the chain extender is present in the oil phase in an amount of about 0.5% to about 10% by weight, or about 1% to about 5% by weight, based on the dry weight of the oil phase.

[0368] In some embodiments, the oil phase further comprises an organic solvent or 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, the organic solvent or diluent is present in the oil phase in an amount of about 5% to about 35% by weight based on the weight of the oil phase, including 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, the organic solvent or diluent is present in the oil phase in an amount of about 10% to about 30% by weight based on the weight of the oil phase.

[0369] The polyol may be present in the oil phase in an amount of about 1% to about 40% by weight, based on the dry weight of the oil phase, including 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, the polyol is present in the oil phase in an amount of about 5% to about 25% by weight, based on the dry weight of the oil phase.

[0370] The weight percentage of the water-soluble polymer in the aqueous phase is calculated by the amount present in the oil phase due to interaction with the oil phase itself and / or oil phase components (e.g., the first adduct, the optional second multifunctional crosslinker). The water-soluble polymers described herein may be present in the aqueous phase in an amount of about 0.5% to about 15% by weight of the dry weight of the oil phase, including 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 polymers described herein are present in the aqueous phase in an amount of about 3% to about 12% by weight, or about 5% to about 10% by weight of the dry weight of the oil phase.

[0371] The water-soluble polymer can be a reactive water-soluble polymer that crosslinks with one or more of the first adduct and the third multifunctional crosslinker (if present). In some embodiments, the water-soluble polymer is a reactive water-soluble polymer that crosslinks with the first adduct, the third multifunctional crosslinker (if present), the third adduct (if present), or any combination of two or more thereof.

[0372] In some embodiments, the water-soluble polymer is a non-reactive water-soluble polymer and does not covalently bond to any component in the oil or water phase (e.g., the first adduct, the third multifunctional crosslinker (if present), the third adduct (if present), or any combination of two or more thereof).

[0373] In some embodiments, the aqueous phase further comprises a water-soluble low molecular weight chain extender or crosslinker. The inclusion of a water-soluble low molecular weight chain extender or crosslinker can increase the degree of crosslinking of the random polymerization product. Examples of water-soluble low molecular weight chain extenders or crosslinkers include, but are not limited to, polyfunctional amines such as ethylenediamine, diethylenetriamine, and triethylenetetramine.

[0374] In some embodiments, the aqueous phase further comprises a surfactant. In some embodiments, the surfactant is a non-ionic surfactant. In some embodiments, the non-ionic surfactant preferably has an average HLB (hydrophile-lipophile balance) value of about 12 to about 15. Non-ionic surfactants include, but are not limited to, TRITON® X-114 ((1,1,3,3-tetramethylbutyl)phenyl-polyethylene glycol), SILWET™ L-7604 (siloxane polyalkylene oxide copolymer), and combinations thereof.

[0375] The weight percentage of surfactant in the aqueous phase is calculated by the amount present in the oil phase due to interaction with or adsorption to the oil phase. The surfactant may be present in the aqueous phase in an amount of about 0.01% to about 2% by weight, based on the dry weight of the oil phase. 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, the surfactant is present in the aqueous phase in an amount of about 0.05% to about 2% by weight, or about 0.1% to about 1% by weight, based on the dry weight of the oil phase.

[0376] In some embodiments, the aqueous phase further comprises an antifoaming or anti-foaming agent, hi some embodiments, the antifoaming agent is FOAMSTAR® ST 2410 (a star polymer-based antifoaming agent).

[0377] The polyethyleneimine intermediates can be used as antimicrobial compounds. In some embodiments, the quaternization is on the pendant substitutions rather than on the polyethyleneimine backbone. Thus, in another aspect, [ka] or a copolymer of any two or more thereof, wherein: Each Y 3 are independently H or -OY 2 and for all Y 3 But it cannot be H, Each Y 2 are independently H or -C(O)-NHR 30 and for all Y 2 -C(O)-NHR 30 It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 -N + (R 20 )3X - and each R 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl; Each R 21 are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10C1-C6 alkyl optionally substituted with a substituent selected from -(aryl), and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 alkyl, and (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, 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 X - is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

[0378] In some embodiments, each Y 2 is H. In some embodiments, the compound is [ka] wherein each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000.

[0379] The second adduct, which is the random polymerization product of the polyethyleneimine intermediate and a (multifunctional) crosslinker disclosed herein, can be used as an antimicrobial compound. Thus, in another aspect, provided herein is a random polymerization product of a polyethyleneimine intermediate and a crosslinker, wherein the polyethyleneimine intermediate is [ka] or a copolymer of any two or more thereof, wherein: Each Y 3 are independently H or -OY 2 and for all Y 3 But it cannot be H, Each Y 2 are independently H or -C(O)-NHR 30 and for all Y 2 -C(O)-NHR 30 It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 -N + (R 20 )3X - and each R 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl; Each R 21 are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 C1-C6 alkyl optionally substituted with a substituent selected from -(aryl), and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 alkyl, and (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, 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 X - is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

[0380] In some embodiments, the crosslinking agent is a polyisocyanate. In some embodiments, 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-cyclohexylisocyanate) (H12MDI), meta-tetramethyl xylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI). In some embodiments, the polyisocyanate is independently selected from the group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T-series polyisocyanates, and LUPRANATE® M-series polyisocyanates.

[0381] In some embodiments, the random polymerization product is of formula (I): [ka] During the ceremony, Each A is independently [ka] or a copolymer of any two or more thereof, wherein the attachment of each A forms a carbamate linkage; Each Y 3 are independently H or -OY 2 and for all Y 3 But it cannot be H, Each Y 2 are independently H or -C(O)-NHR 30 and for all Y 2 -C(O)-NHR 30 It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 -N + (R 20 )3X - and each R 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl; Each R 21 are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 C1-C6 alkyl optionally substituted with a substituent selected from -(aryl), and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 Alkyl, (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, and (3) [ka] wherein each R ais 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 are independently -(C-C optionally substituted with phenyl) 10 alkylene)- or a 3- to 8-membered cycloalkyl ring; each X - is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

[0382] In some embodiments, the random polymerization product is of formula (II): [ka] During the ceremony, Each A is independently [ka] or a copolymer of any two or more thereof, wherein the attachment of each A forms a carbamate linkage; Each Y 3 are independently H or -OY 2 and for all Y 3 But it cannot be H, Each Y 2 are independently H or -C(O)-NHR 30 and for all Y 2 -C(O)-NHR 30 It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C2-C6 alkylene)-; Each R 10 -N + (R 20)3X - and each R 20 are independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; 18 Heteroalkyl, and C-C optionally substituted with -(C-C alkyl), -(C-C alkoxy), -C(O)O-(C-C alkyl), -C(O)NH(C-C alkyl), -C(O)N(C-C alkyl), or -OC(O)-(C-C alkyl). 10 aryl; Each R 21 are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 C1-C6 alkyl optionally substituted with a substituent selected from -(aryl), and -(C1-C6 alkoxy) optionally substituted with -OH; Each R 30 are independently: (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C-C optionally substituted with 1 to 3 substituents independently selected from 20 Alkyl, (2) halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C optionally substituted with 1 to 3 substituents independently selected from 10 aryl, and (3) [ka] 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 are independently -(C-C optionally substituted with phenyl) 10 alkylene)- or a 3- to 8-membered cycloalkyl ring; each X - is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

[0383] It will be appreciated that the polymers described herein and the general methods for preparing them offer considerable versatility for tuning and fine-tuning their physical and chemical properties, as well as their antimicrobial properties, for a wide range of different surfaces, substrates, and applications. Examples of variables available for this tuning include, but are not limited to, the structure and amount of the first quaternary ammonium salt, optional polyol, optional chain extender, water-soluble polymer, first multifunctional crosslinker (e.g., first polyisocyanate), polyethyleneimine intermediate or second adduct (including its second multifunctional crosslinker, e.g., second polyisocyanate), optional third multifunctional crosslinker (e.g., third polyisocyanate), optional second quaternary ammonium salt, optional fourth multifunctional crosslinker (e.g., fourth polyisocyanate), and the degree of crosslinking. It will also be understood that multifunctional crosslinker(s) other than polyisocyanates may be used, such as, but not limited to, multifunctional epoxides, imines, carbodiimides, and aldehydes.

[0384] In another aspect, provided herein is an antimicrobial coating, coating fluid, or spray fluid comprising, consisting essentially of, or consisting of the antimicrobial composition described herein. In some embodiments, the coating fluid or spray fluid is water-soluble or water-dispersible.

[0385] In another aspect, provided herein is a device, apparatus, equipment, or accessory comprising the antimicrobial coating, coating fluid, or spray fluid described herein. Non-limiting examples of devices, apparatus, equipment, or accessories include filters, air purifiers, masks or other personal protective devices (PPDs), respirators, etc. Other non-limiting examples include keyboards, keypads, stylus pens, mice, remote controls, touchscreens, phones, and displays, or any device integrating any of the foregoing components.

[0386] In another aspect, provided herein is a personal care appliance comprising the coating, coating fluid, or spray fluid described herein. Non-limiting examples of personal care appliances include facial tissues, hand soaps, and cleansing pads.

[0387] How to use In another aspect, provided herein is a method of disinfecting a surface, the method comprising, consisting essentially of, or consisting of applying to the surface a composition disclosed herein.

[0388] In another aspect, provided herein is a method of reducing (e.g., minimizing) antimicrobial growth on a surface, the method comprising, consisting essentially of, or consisting of applying to the surface a composition disclosed herein. In some embodiments, the method comprises forming a coating solution containing a composition according to any of the embodiments described herein. The method further comprises directing the coating solution to the surface via an applicator (e.g., a sprayer) and providing a coating on the surface through application of the coating solution to the surface.

[0389] In another aspect, provided herein is a method of preventing antimicrobial growth on a surface, the method comprising, consisting essentially of, or consisting of applying to the surface a composition disclosed herein.

[0390] In some embodiments of the above-described methods, the applying step comprises, consists essentially of, or consists of spraying or brushing the surface with the composition. In some embodiments of the above-described methods, the applying step comprises, consists essentially of, or consists of immersing the surface in a coating solution containing a composition according to any of the embodiments described herein. In some embodiments of the above-described methods, the applying step comprises, consists essentially of, or consists of applying the composition to the surface by an electrostatic process.

[0391] The description of the embodiments of the present disclosure is not intended to be exhaustive or to limit the disclosure to the precise form disclosed. Specific embodiments and examples of the present disclosure are described herein for illustrative purposes; however, those skilled in the relevant art will recognize that various equivalent modifications are possible within the scope of the present disclosure. For example, while method steps or functions are presented in a given order, alternative embodiments may perform the functions in a different order, or the functions may be performed substantially simultaneously. The teachings of the present disclosure provided herein can be applied to other procedures or methods, where appropriate. The various embodiments described herein can be combined to provide further embodiments. Aspects of the present disclosure can be modified, if necessary, to employ compositions, functions, and concepts from the above-mentioned references and applications to provide still further embodiments of the present disclosure. Furthermore, due to considerations of biological functional equivalence, some changes can be made in protein structure without affecting the type or amount of biological or chemical activity. These and other changes can be made to the present disclosure in light of the detailed description. All such modifications are intended to be within the scope of the appended claims.

[0392] Specific elements of any of the foregoing embodiments may be combined with or substituted for elements of other embodiments. Furthermore, although advantages associated with certain embodiments of the present disclosure are described in the context of those embodiments, other embodiments may also exhibit such advantages, and not all embodiments necessarily exhibit such advantages to fall within the scope of the present technology.

[0393] The technology described herein is further exemplified by the following examples, which should not be construed as further limiting in any way. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of this disclosure, suitable methods and materials are described below. [Example]

[0394] Having now generally described the present technology, it will be more readily understood by reference to the following examples, which are included solely for the purpose of illustrating certain aspects and embodiments of the technology and are not intended to limit the technology.

[0395] Evaluation of the antiviral activity of polymers and / or their coatings Evaluation of the antiviral activity of the polymer coating of the present technology was carried out as follows: All samples and all accessories for evaluation were first disinfected by either high temperature autoclaving, alcohol cleaning, or irradiation in a UV laminar flow chamber.

[0396] First, adenovirus (108 PFU / mL, plaque-forming units, MOI = 100) was inoculated into 2 × 10 7 The virus solution was diluted to PFU / ml, and 0.1 mL of the diluted virus solution was then deposited onto the disinfected sample.

[0397] The antiviral activity was determined by two different methods: (i) a human cell (HuH7) method, and (ii) a quantitative reverse transcription polymerase chain reaction (RT-qPCR) method.

[0398] (i) Human cell (HuH7) method Huh7 is a type of human liver cell line that can be grown in the laboratory for research purposes. According to the website huh7.com, it is "a cancer cell line derived from well-differentiated liver cells originally isolated from a liver tumor in a 57-year-old Japanese man in 1982."

[0399] To evaluate antiviral activity, 0.1 mL of virus (adenovirus) in Dulbecco's Modified Eagle Medium (DMEM) + 10% fetal bovine serum (FBS) was dropped onto the coating and onto a control substrate and left on the coating for 30 minutes. The virus / medium mixture was transferred to a Petri dish containing HuH7 cells (human hepatocytes) in medium. Residual virus on the coating was rinsed twice by combining 0.1 mL of medium and liquid with the virus solution in the Petri dish. The Petri dish was transferred to a CO2 incubator and incubated at 37°C with approximately 95% relative humidity and 5% CO2 for 48 hours to amplify the signal.

[0400] Once incubation was complete, visible and fluorescent micrographs of the virus / cell samples were taken to determine the virus and live / dead cell populations. For the positive control, 0.1 mL of virus in medium was transferred directly to a Petri dish containing HuH7 cells in medium.

[0401] (ii) RT-qPCR method RT-qPCR is used in a variety of applications, including pathogen detection, gene expression analysis, RNAi validation, microarray validation, genetic testing, and disease research.

[0402] Sample preparation The medium (DMEM, high sucrose, pyruvate; ThermoFisher, Cat. No.: 11995040) was removed from the refrigerator and conditioned in a 37°C water bath for 30 minutes.

[0403] Preparation of virus solution: Typical virus numbers for stock are 5 lambda (5x10) per tube. 8) Add 1 mL of DMEM medium to the virus tube, mix the tube evenly with a vortex mixer for 5 to 10 seconds, and then mix 5 x 10 8 The virus solution was diluted to 5 × 10 / mL in DMEM medium for antiviral testing. 7 / mL.

[0404] RT-qPCR procedure for coating: The coated film was immersed in 99% alcohol for 1 second. Excess alcohol was removed from the surface. The film was then air-dried in a new Petri dish for 15-20 minutes. Then, 100 μL of diluted virus solution (5 × 10 6 A drop of 1000 uL of 1X PBD was placed on the dried film. The Petri dish was covered and the virus was allowed to contact the film for the desired contact time. In some experiments, the contact time was reduced to as little as 30 seconds. The virus fluid from the film was transferred to an Eppendorf tube. The film was then rinsed twice with 50 μL of 1X PBD, and the rinse fluid was combined with the Eppendorf tube. The total test volume was 200 μL and ready for DNA extraction.

[0405] RT-qPCR procedure for aqueous solutions: Add 100 µL of test sample to 100 µL of diluted virus flow (5 x 10) in an Eppendorf tube. 7 / mL) and the mixture (5 × 10 6 The virus count was measured and shaken for 30 minutes on a shaker. DNA was extracted using a Novogene DNA kit according to the specified extraction procedure.

[0406] RT-qPCR testing: Each sample was tested in quadruplicate. The components listed in Table 1 were mixed thoroughly in an Eppendorf tube. [Table 1] [Table 2]

[0407] Ten microliters of the premix was added to each cavity of the test plate, and three samples were taken for each coating, with each sample run in quadruplicate, for a total of 12 tests for each coating.

[0408] The plate was centrifuged to ensure that all premix fluid had flowed to the bottom of the cavity. The plate was then inserted into Applied Biosystems QuantStudio 3 (ThermoFisher) to determine the cycle threshold (CT) number for calculating antiviral efficacy. Antiviral efficacy was quantitatively calculated from the CT number.

[0409] test Qualitative cell viability test of coating: The coating was placed in a Petri dish, and 100 μL of DMEM medium was dropped onto the coating. The Petri dish was then covered for 30 minutes. The medium on the film was then removed by adding 8 × 10 cells in 500 μL of medium in each fraction. 4 The film was then transferred to a cell plate containing 100 cells. The film was rinsed twice with 50 μL of DMEM medium, and the resulting fluid was combined with the previous test fluid in the same location in the plate. A total of 200 μL of test fluid was added to the 500 μL of cells / medium. The cell plate was incubated in a 37°C / 95% RH CO2 incubator for 48–96 hours, after which cell growth and morphology were observed under a visible microscope. Dead cells floated or suspended in the medium, while live cells remained fixed to the bottom of the plate. This test was intended to assess the contact cytotoxicity of the polymer film. If this test indicates some degree of cytotoxicity, the actual mechanism of cell death is not given, although cell death due to extraction of chemicals from the coating is one possibility.

[0410] Qualitative cell viability testing of polymer solutions or dispersions: 100 μL of polymer solution or dispersion and 100 μL of DMEM medium were added to an Eppendorf tube and thoroughly mixed on a shaker for 30 minutes. For polymer films, a fixed area of ​​the film was cut and dispersed in the medium for testing. The test fluid was transferred to a cell plate, and cells were grown in a 37°C / 95% RH CO2 incubator for 48-96 hours. Cell growth and morphology were recorded under a visible microscope.

[0411] Qualitative antiviral efficiency test of polymer films: 100 μL of virus solution (5 × 10 7 8 × 10 virus suspensions (8 × 10 virus suspensions / mL) were dropped onto a polymer film in a Petri dish. The Petri dish was covered for 30 minutes. The virus suspension was added to 8 × 10 virus suspensions in 500 μL of medium in each fraction. 4 The film was then rinsed twice with 50 μL of DMEM medium, and the resulting fluid was combined with the previous test fluid in the same location within the plate. The total volume of the test fluid was 200 μL. The cell plate was then incubated in a 37°C / 95% RH CO2 incubator for 48 to 96 hours. Finally, cell morphology and fluorescence were recorded under a UV microscope.

[0412] Qualitative antiviral efficiency test of polymer solution or dispersion: 100 μL of virus solution (5 × 10 7 100 μL of the polymer solution or dispersion was added to the Eppendorf tube and thoroughly shaken on a shaker for 30 minutes. The test mixture was added to 8 × 10 cells in 500 μL of medium for each fraction. 4 The cells were added to a cell plate containing 1000 cells. 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.

[0413] Examples 1-4. Water-based coatings containing water-soluble polyethyleneimine intermediates [Table 3]

[0414] Preparation of the aqueous phase: 3.1 parts of HEC 380K (2-hydroxyethyl cellulose, average Mw=380,000) from Aldrich was completely dissolved in 96.9 parts of DI water. The pH of the solution was adjusted to 4.5 with a 5% solution of H3PO4.

[0415] Comparative Example 1: Preparation and Antiviral Activity Evaluation Preparation of oil phase: 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 DESMODUR® N100 in 5 g of dry toluene at 90° C. under nitrogen and allowed to react for 15 hours. After removing the toluene under reduced pressure, a clear viscous liquid (first adduct) was obtained.

[0416] 4.144 parts of the first adduct (N100-C18DMDEG(Br-)), 0.356 parts of PTMG 1000 (poly(tetramethylene glycol) from Aldrich, average Mn=1000), 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 solids content reached approximately 90% by weight. 0.828 parts of polyisocyanate N100 (DESMODUR N100 from Convestro) and 1.276 parts of dry acetone were added to the solution and mixed homogeneously.

[0417] Preparation of oil-in-water emulsions and coatings The aqueous phase solution prepared above was added to the oil phase at room temperature and emulsified by sonication (100 watts) for 10 seconds, five times with 10-second pulses between each sonication. The total emulsification time was approximately 90-120 seconds. The resulting oil-in-water emulsion was coated onto 2-mil corona-treated white PET (Melinex 339, Teijin) and dried at room temperature for 10 minutes, followed by 15 hours at 60°C. The resulting film exhibited acceptable film properties and resistance to alcohol and water disinfection processes. Its antiviral efficacy against adenovirus was measured by q-RT-PCR as described above.

[0418] Examples 2 to 4 The same procedure described in Example 1 was repeated for the preparation of 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%.

[0419] Preparation of QPEI 37169 [ka] QPEI 37169 was prepared as shown in the reaction scheme above.

[0420] For the purposes of the chemistry described herein, the ratio of primary, secondary, and tertiary amines in branched PEI is assumed to be 1:2:1, as reported in the literature. 24、25 .

[0421] The procedure used was essentially as described in Gao et al. (2007). 26 The structure of QPEI 37169 is intended to be an approximation indicating that most of the primary and secondary amines have reacted with the epoxide and most of the tertiary amines have been quaternized by alkylation with benzyl chloride.

[0422] To a 25 mL two-neck flask under nitrogen, 3.33 g of 70 kDa PEI solution (30% / 1 g PEI in water, mw = 43.1 g / mol, assuming 23.2 mmol) was added and cooled to 0 °C. To this mixture, 5.4 g (92.8 mmol) of propylene oxide was added dropwise at 0-3 °C. After the addition was complete, the reaction mixture was stirred at 0-3 °C for 7 h. The temperature of the reaction mixture was then raised to 35 °C, and unreacted propylene oxide was distilled (approximately 3.60 mL). To the resulting solution, 11.75 g (10.6 mL, 92.8 mmol) of benzyl chloride was added, and the reaction was heated to 50 °C for 30 h. The reaction was extracted with diethyl ether (3 × 20 mL) to remove unreacted benzyl chloride, residual propylene oxide, and any lipophilic by-products or impurities (if present). The aqueous phase was separated, evaporated under vacuum, and dried by lyophilization to leave QPEI 37169 as a clear solid (2.85 g). The product was characterized by proton NMR and infrared (IR) spectroscopy.

[0423] Preparation of QPEI HB37169 The same reaction as in the preparation of QPEI 37169 was used to prepare QPEI HB37169, except that hyperbranched polyethyleneimine of the same molecular weight was used.

[0424] Preparation of QPEI HB37478 The same reaction as in the preparation of QPEI 37169 was used to prepare QPEI HB37478, except that the quaternizing agent benzyl bromide was replaced by hexyl bromide and a hyperbranched polyethyleneimine of the same molecular weight was used.

[0425] Substitution of 5 wt % of the first adduct (N100-C18DMDEG(Br-)) with three polyethyleneimine intermediates (QPEI) significantly improved the antiviral efficiency even at contact times as short as 30 s (see Table 2).

[0426] Examples 5-9. QPEI 37169 as a Polyethyleneimine Intermediate in Aqueous Phase [Table 4]

[0427] The compositions of Examples 5-9 were prepared using the same procedures as in Examples 1-4, except that the compositions were modified as shown in Table 3. All coatings exhibited acceptable film properties, water resistance, and alcohol resistance.

[0428] All coatings showed antiviral efficiency greater than 99.95% at a contact time of 30 minutes.

[0429] Examples 10-20 illustrate additional examples of polyethyleneimine intermediates or second adducts that can be used in the present technology.

[0430] Example 10. Synthesis of Polyethyleneimine Intermediate 40840 [ka] A 500 mL three-necked round-bottom flask was equipped with a thermometer, a condenser, and a magnetic stirrer. The reaction flask was flushed with nitrogen gas and the reaction was carried out under a stream of nitrogen gas.

[0431] 10 g of PEI (70 kDa branched, 30 wt% aqueous solution, amine content 18 mmol / g solid polymer, primary:secondary:tertiary amine ratio = 1:2:1), potassium carbonate (37.07 g, 0.232 mol), and 150 mL of t-amyl alcohol were added to a round-bottom flask. The mixture was stirred under nitrogen for 30 min, 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 h.

[0432] 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, forming a white precipitate. 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 on a rotary evaporator and then further dried under high vacuum for 5 hours. The yield of the dried product was then 17.4 g. The product was 1 Characterized by 1 H NMR and analyzed for the degree of quaternization using Mohr silver titration to determine the amount of bromide.

[0433] Example 11. Synthesis of Polyethyleneimine Intermediate 40660 [ka]

[0434] A 2 L three-necked round-bottom flask was fitted with a dropping funnel, a condenser, and a magnetic stirrer. The reaction flask was flushed with nitrogen gas and the reaction was carried out under a stream of nitrogen gas.

[0435] 10 g of PEI (70 kDa branched, 30% by weight aqueous solution, amine content 18 mmol / g solid polymer, primary, secondary, and tertiary amine ratio = 1:2:1) was added to a reaction flask, and 835 mL of water was added to it. 114.3 g of glycidyltrimethylammonium chloride (0.754 mol, approximately 4 equivalents based on 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 vigorously stirred at room temperature for 4 days, after which the reaction mixture was a single clear phase. All solvents were removed on a rotary evaporator at 55 °C. The pasty liquid residue was dissolved in 200 mL of methanol, and the polymer 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 on a rotary evaporator and then under high vacuum to give 46.5 g of the final product. 1 Characterized by 1 H NMR and analyzed for the degree of quaternization using Mohr silver titration to determine the amount of chloride.

[0436] Example 12. Synthesis of Polyethyleneimine Intermediate 40818 [ka]

[0437] A 100 mL single-neck round-bottom flask was fitted with a condenser, a heating cup, and a magnetic stirrer. The reaction flask was flushed with nitrogen gas and the reaction was carried out under a stream of nitrogen gas.

[0438] 2 g of glycidyl-functionalized PEI (3.3 mmol, 13.3 mmol reactive N), bromohexane (7 g, 40 mmol, 3 equiv.), and 4.4 mL of t-amyl alcohol were added to a flask, and the reaction mixture was heated at 96° C. for 96 hours. The reaction mixture turned from colorless to pale orange. The reaction was cooled to room temperature, and the resulting solution was poured into tertiary butyl methyl ether (TBME) with vigorous stirring, causing a precipitate to form. The liquid was decanted from the precipitated solid, which was dissolved in methanol and reprecipitated with TBME. This process was repeated three times, yielding 4.06 g of product after drying on a rotary evaporator and then under high vacuum. The product was 1 They were characterized by 1 H NMR and analyzed for the degree of quaternization using Mohr silver titration to determine the amount of halide.

[0439] Example 13. Evaluation of adenovirus activity in Examples 10 and 11 Aqueous solutions of polyethyleneimine intermediates 40840 and 40660 were evaluated for antiviral activity as described above. [Table 5]

[0440] Example 14. Synthesis of a monoisocyanate-capped polyethyleneimine intermediate (approximately 85% of free OH groups) As shown below, the structure of the polymer product is intended to be an approximation showing that the majority of the hydroxyl groups (approximately 85% molar equivalents) react with the blend of monoisocyanates to form a urethane, with some hydroxyl groups remaining unreacted. [ka]

[0441] The concentration of reactive hydroxyl groups (mmol / gram of dry polymer) was determined by titrating a known amount (grams) of dry hydroxyl alkyl quaternary polyethyleneimine (HA-Q-PEI) with a known excess (grams, mmol) of octadecyl isocyanate. The percentage of monoisocyanate consumed in the reaction was determined by monitoring the reaction progress using infrared (IR) spectroscopy at 2263 cm. -1 The isocyanate concentration was determined by monitoring the decrease in the isocyanate peak at 100°C. From the percentage decrease in this peak, the number of millimoles of isocyanate consumed was estimated. This value corresponded to the number of millimoles of polymer hydroxyl groups that reacted with isocyanate. In this way, the hydroxyl group concentration of the polymer (mmoles reactive hydroxyl groups / g dry polymer) was calculated and then used in subsequent reactions to determine the amount of monoisocyanate(s) needed to functionalize a specific percentage of reactive hydroxyl groups in the polymer, thereby fine-tuning the hydrophilic / hydrophobic properties of the polymer.

[0442] 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 2 hours, followed by storage in a desiccator at room temperature overnight. To the dried polymer, 13.8 g of t-butyl alcohol and 9.2 g of dimethylacetamide were added. The resulting mixture was stirred under nitrogen until the polymer was completely dissolved. Both of these solvents were thoroughly dried over 4 Å molecular sieves before use. 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 totaled 7.73 mmol of monoisocyanates, corresponding to approximately 85% of the available hydroxyl groups. The reaction mixture became slightly cloudy. The resulting reaction mixture was stirred at room temperature under nitrogen for 12 hours. The resulting reaction mixture was filtered through a PTFE filter (1 μm pore size) to yield 20.83 grams of QPEI 37169 caps as a 12.19% solid solution. IR spectroscopy showed the expected new peaks corresponding to the urethane carbonyl and no residual isocyanate peaks.

[0443] In some embodiments, after the reaction with the monoisocyanate(s) was complete, the reaction mixture was added to water to precipitate the capped product. The product was isolated, washed with water to remove any water-soluble impurities, and then dried for use in the next step. This water precipitation step was useful for removing any water-soluble impurities that could contribute to toxicity.

[0444] Example 15. Process for the crosslinking and coating reaction of octadecyl / octylurethane quaternary ammonium PEI (example of second adduct formation) As shown below, the structure of polymeric compound (A) is intended to be an approximation indicating that some of the unreacted hydroxyl groups in the QPEI 37169 cap reacted with polyisocyanate to form urethane crosslinks. [ka]

[0445] Using the procedure described in Example 15, 20 g of octadecyl / octylurethane quaternary ammonium PEI was prepared, to which 1.25 g of Desmodur N3300 (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 with a #36 Mayer rod onto corona-pretreated white PET (2 mil, Milenex 339) supported on a stainless steel plate. The coated film was heated in an oven at 60°C for 30 minutes without vacuum. This dried film was used to measure antimicrobial activity. IR spectroscopy showed no residual isocyanate.

[0446] It should be noted that the above crosslinking procedure has also been carried out without the dibutyltin dilaurate catalyst, and although the resulting dry film was somewhat less durable than when the catalyst was used, it still provided a reasonable coating.

[0447] Example 16. Aqueous antiviral efficiencies against adenovirus of HA-Q-PEI polymers with various PEI molecular weights, nitrogen quaternized groups, and anionic counterions The following formula: [ka] A variety of HA-Q-PEIs (hydroxyalkyl quaternary PEIs) were prepared using procedures similar to those described in Example 2 (preparation of QPEI 37169) and analyzed for their antiviral (AV) efficacy against adenovirus as described above. Selected data are shown in Table 5 (R1 = methyl for each polymer). These results demonstrate high antiviral efficacy across a range of PEI molecular weights using various nitrogen quaternizing groups (R2) and anionic counterions (X-). [Table 6]

[0448] Example 17. Aqueous antiviral efficiency of HA-Q-PEI polymers with various PEI molecular weights against adenovirus The following formulas with various molecular weights: [ka] Additional HA-Q-PEI polymers (R1 = methyl, R2 = hexyl, X = bromide) were prepared using procedures similar to those described in Example 2 (Preparation of QPEI 37169) and analyzed for their antiviral (AV) efficacy against adenovirus as described above. Selected data are shown in Table 6. [Table 7]

[0449] These results demonstrate that for this series of HA-Q-PEI polymers, the solution antiviral efficiency against adenovirus increases as the PEI molecular weight increases, leveling off at a maximum of >99% within the range of 25,000–270,000.

[0450] Although these HA-Q-PEI polymers exhibit high solution antiviral efficacy, their high water solubility makes them unsuitable for the fabrication of durable, water-resistant surface coatings. Coating durability against solvents such as water and ethanol is highly desirable, as it maintains antibacterial efficacy and significantly reduces the need for frequent re-sterilization of surfaces after they have been cleaned by washing.

[0451] Example 18. Adenoviral Antiviral Efficacy of Second Additive as Antimicrobial Agent in Coating as a Function of Weight Percentage of N100 Crosslinker Used The following formula: [ka] was prepared using a procedure similar to that described in Example 15, replacing octadecyl / octyl urethane quaternary ammonium PEI with HA-Q-PEI (prepared from PEI: MW=70,000 (branched), R1=methyl, R2=hexyl, X=bromide) to prepare a second adduct coating of crosslinker Z (DESMODUR® N100): [ka] The amount of each was varied.

[0452] These second adducts were investigated for antiviral efficacy against adenovirus (procedure described above), and the selected data are shown in Table 7. [Table 8]

[0453] Cross-linking 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 by this example, this was associated with a significant decrease in antiviral efficacy with increasing amounts of cross-linking.

[0454] Example 19 Antiviral Efficacy Against Adenovirus of Polyethylenimine Intermediates with or without Monoisocyanate Substitution as Non-Crosslinked Coatings The following formula: [ka] Polyethylenimine intermediate (MUA-Q-PEI-A polymer, where R3 = C 18HA-Q-PEI (prepared from PEI: molecular weight = 70,000 (branched), R1 = methyl, R2 = benzyl) and a monoisocyanate mixture (octadecyl isocyanate to octyl isocyanate in a 7:3 ratio), in which approximately 90% of the HA-Q-PEI hydroxyl groups reacted with the monoisocyanate mixture (see similar protocol in Example 14). MUA-Q-PEI-A100 polymer was similarly prepared, in which approximately 100% of the HA-Q-PEI hydroxyl groups reacted with the monoisocyanate mixture. Films of these MUA-Q-PEI-A and MUA-Q-PEI-A100 polymers were examined for their antiviral efficacy against adenovirus, as described above. The results are shown in Table 8. [Table 9]

[0455] These results indicate that the high solution antiviral efficacy of the HA-Q-PEI polymer was maintained and / or increased after reaction with the monoisocyanate mixture to form coatings of the MUA-Q-PEI-A and MUA-Q-PEI-A100 polymers. These results also demonstrate that the coatings exhibited >99% antiviral efficacy even at contact times as short as 30 seconds.

[0456] Example 20 Second Adduct Coating Antiviral Efficiency Against Adenovirus and Coating Durability as a Function of the Amount (Weight Percent) of N3300 Polyisocyanate Crosslinker Used The following formula: [ka] the second adduct (PUA-Q-PEI-B polymer, where R3 = C 18Alkyl or C8 alkyl) were prepared using a procedure similar to that described in Example 14. In particular, HA-Q-PEI (prepared from PEI: MW=25,000 (hyperbranched), R1=methyl, R2=hexyl, X=bromide) was reacted with a monoisocyanate mixture (7:3 ratio of octadecyl isocyanate to octyl isocyanate) in which approximately 90% of the HA-Q-PEI hydroxyl groups reacted with the monoisocyanate mixture, and then the remaining hydroxyl groups were cross-linked with various amounts of cross-linker Z (DESMODUR® N3300): [ka] and reacted with

[0457] These PUA-Q-PEI-B polymer coatings were evaluated for their antiviral efficacy against adenovirus (procedure described above), water durability, and ethanol durability. The general procedure for measuring water and ethanol durability was to immerse a center cross-cut coating sample in water or ethanol for 10 minutes, followed by gently wiping the sample with a cotton swab. Intact coatings passed the test. Selected data are shown in Table 9. [Table 10]

[0458] This data suggests that crosslinker is necessary to achieve good durability, and that for these samples there was an optimal range of crosslinker levels where antiviral efficacy was >99% and above which antiviral efficacy significantly decreased.

[0459] Example 21. Antibacterial and antiviral tests The coating samples from Table 10 were prepared in a manner similar to that described in Examples 1-4. [Table 11] [ka]

change

[0460] The QPEI for these coatings was prepared as follows: To a 500 mL four-neck round-bottom flask equipped with a reflux condenser, addition funnel, thermometer, and KPG stirrer with a side stirrer blade, 20 g of EPOMIN™ P-1050 (PEI 70 kDa with a 1:2:1 ratio of primary to secondary to tertiary amines and an amine content of 18 mmol / g of polymer), 150 ml of t-amyl alcohol, and 32.1 g (232 mmol) of K2CO3 were added. The mixture was stirred under nitrogen gas at 200 rpm at 25-30°C for 30 minutes. To this reaction mixture, 6.5 g (46 mmol) of 3-bromo-1-propanol dissolved in 145.5 g (881 mmol) of 1-bromohexane was added dropwise over 30 minutes at 25-30°C. After the addition was complete, the temperature was increased to 96°C and the reaction mixture was stirred at 96-98°C for 98 hours, resulting in a light brown solution. The reaction mixture was cooled to 25-30°C and filtered (Büchner funnel), rinsing the filter with 50 mL of tert-amyl alcohol. The filtrate was concentrated to dryness under vacuum below 50°C, and 200 mL of diethyl ether was added to the residue at 25-30°C. This mixture was stirred for 30-60 minutes, during which time a brown slurry formed. The stirring was stopped, and the solid was allowed to settle for 30-60 minutes. The supernatant liquid was decanted. The supernatant liquid (ether suspension) was decanted several times (5-6 times) until the amount of alkyl halide in the decanted liquid was less than 0.5% by GC analysis. The remaining liquid was distilled from the solid under vacuum in a rotary evaporator at below 40°C. The sticky off-white material was dissolved in methyl ethyl ketone at 25-30°C to obtain a slightly hazy solution, which was filtered through a bed of Celite, after which a clear solution was observed. Distillation of the solvent under reduced pressure in a Rota evaporator at 45°C resulted in a solid mass. The solid mass was dried below 45°C for 6-8 hours. The product was isolated as an off-white solid in a yield of 39.4 g. The theoretical mole percentages for the PEI reaction with 1-bromopropanol and 1-bromohexane are 5% and 95%, respectively, assuming similar alkylation rates between the two alkyl halides.

[0461] The coated samples from Table 10 were tested against a wide range of viruses and bacteria, as well as fungi and microalgae, according to ISO standard 21702:2019. Selected data is shown below in Tables 11, 12, 13, and 14. Positive values ​​reflect a percent reduction in microbial population. Negative log values ​​indicate an increase in microbial population. [Table 12] [Table 13] [Table 14] [Table 15]

[0462] Coated Sample 3 from Table 10 was tested for antiviral and antibacterial efficiency after being subjected to wet abrasion (PAS Standard 2424:2014 pt. 9.2.4) or dry abrasion (PAS Standard 2424:2014 pt. 9.2.2). The data is shown in Table 15. [Table 16]

[0463] Non-limiting examples of QPEIs that can be incorporated into the technology disclosed herein are set forth below.

[0464] Example 22. Compound 22-1 Compound 22-1 is similar to QPEI samples 3-8 and 3-9 in Example 17 and was prepared from PEI with a MW of 270 kDa. Compound 22-1 (batch 105159) contains a greater than 1:1 ratio of hexyl halide nitrogen functionalization to propylene oxide nitrogen functionalization (i.e., there are more hexyl groups than 2-hydroxypropyl groups on the nitrogen atom). Compound 22-1 (batch 99367) contains an approximately 1:1 ratio of hexyl halide nitrogen functionalization to propylene oxide nitrogen functionalization (i.e., the number of hexyl groups is approximately equal to the number of 2-hydroxypropyl groups on the nitrogen atom).

[0465] Example 23. Compound 23-1 Compound 23-1 is similar to compound 37478, but was prepared from PEI with a MW of 25 kDa. Compound 23-1 contains approximately a 1:1 ratio of nitrogen functionalization with hexyl halide to nitrogen functionalization with propylene oxide (i.e., the number of hexyl groups is approximately equal to the number of 2-hydroxypropyl groups on the nitrogen atom).

[0466] Example 24. Compound 24-1 Compound 24-1 (Batch 109590) is similar to HB37478 in Example 4, but uses branched 70 kDa PEI rather than hyperbranched 70 kDa PEI. Compound 24-1 (Batch 109590) contains approximately a 1:1 ratio of hexyl halide nitrogen functionalization to propylene oxide nitrogen functionalization (i.e., the number of hexyl groups is approximately equal to the number of 2-hydroxypropyl groups on the nitrogen atom).

[0467] Example 25. Compound 25-1 Compound 25-1 (Batch 105402 and Batch 109634) is similar to QPEI sample 2-9 (prepared from PEI with MW=70 kDa) in Example 16. Compound 25-1 (Batch 105402 and Batch 109634) contains approximately a 1:1 ratio of nitrogen functionalization with phenacyl halide to nitrogen functionalization with propylene oxide (i.e., the number of phenacyl groups is approximately equal to the number of 2-hydroxypropyl groups on the nitrogen atom).

[0468] Example 26. Compound 26-1 Compound 26-1 (Batch 109781) is similar to QPEI 37169 (prepared from PEI of MW=70 kDa) in Example 2. Compound 26-1 (Batch 109781) contains approximately a 1:1 ratio of benzyl halide nitrogen functionalization to propylene oxide nitrogen functionalization (i.e., the number of benzyl groups is approximately equal to the number of 2-hydroxypropyl groups on the nitrogen atom).

[0469] Example 27. Compound 27-1 Compound 27-1 (batch 110417) is similar to compound 25-1 but is prepared from PEI with MW=750 kDA.

[0470] Example 28. Compound 28-1 Compound 28-1 (batch 109831) is similar to polyethyleneimine intermediate 40660 of Example 11 (prepared from PEI of MW=70 kDa).

[0471] Example 29. Compound 29-1 Compound 29-1 (batch 110420) is similar to polyethyleneimine intermediate 40818 of Example 12 (prepared from PEI of MW=70 kDa).

[0472] Example 30. Compound 30-1 Compound 30-1 corresponds to an intermediate compound in the synthesis of QPEI 37169 in Example 2, resulting from the reaction of PEI (MW=70 kDa) with propylene oxide. Therefore, no quaternary amine is present in compound 29-1.

[0473] Example 31. Compound 31-1 [ka]

[0474] A 1 L three-necked round-bottom flask was fitted with a dropping funnel, a condenser, a water bath, and a mechanical stirrer. The flask was flushed with nitrogen gas and the reaction was carried out under a stream of nitrogen gas.

[0475] 20 g of a 50% aqueous solution of 70 kDa branched PEI (10 g of PEI polymer, 0.180 moles of amine content with an approximate 1:2:1 ratio of primary to secondary to tertiary amines) was added to the flask and stirred at approximately 200 RPM. Note that theoretically, the 0.180 moles of nitrogen content at this ratio of primary, secondary, and tertiary amines can react with 0.36 moles of alkyl halide, which is defined as "one equivalent of alkyl halide" in this example.

[0476] tert-Amyl alcohol (150 mL) was added to the flask at ambient temperature, followed by KCO (32.1 g, 0.232 mol). A mixture of bromopropanol (1.29 g, 0.0093 mol) and 1-bromohexane (151.86 g, 0.92 mol) (total alkyl halide = 0.93 mol, molar % content of each alkyl halide = 2.6 equivalents at 1% bromopropanol / 99% 1-bromohexane) was added dropwise over 1-2 hours at ambient temperature.

[0477] The reaction temperature was increased to 96°C and the reaction was stirred at 96°C for 98 hours. The reaction 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 while maintaining 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 trituration and decantation of diethyl ether was repeated 3-4 times until the residual alkyl halide content in the decanted layer was less than 0.5%, as determined by GC analysis.

[0478] After completing the grinding / decantation process, the mixture was evaporated to dryness under reduced pressure, keeping the temperature below 40°C, to yield an off-white sticky solid. This solid was dissolved in methyl ethyl ketone (100 ml) at 25-30°C, filtered through Celite, and the filtrate was evaporated to dryness under reduced pressure at 45°C. The resulting solid was oven-dried at below 45°C for 4-6 hours to yield the product (37.8 g) as an off-white solid. The water content was determined to be 0.24% by Karl Fischer analysis. The bromine content was determined to be 23.6% by AgNO3 titration. The theoretical mole percentages for the PEI reaction with 1-bromopropanol and 1-bromohexane are 1% and 99%, respectively, assuming similar alkylation rates between the two alkyl halides.

[0479] Example 32. Compound 32-1 [ka]

[0480] A 1 L, four-necked round-bottom flask was fitted with a dropping funnel, a condenser, a water bath, and a mechanical stirrer. The flask was flushed with nitrogen gas and the reaction was carried out under a stream of nitrogen gas.

[0481] Ten grams of 25 kDa hyperbranched PEI (0.180 moles of amine content with an approximate 1:1:1 ratio of primary to secondary to tertiary amines) was added to a flask along with 10 ml of water. Note that theoretically, the 0.180 moles of nitrogen content at this ratio of primary, secondary, and tertiary amines can react with 0.36 moles of alkyl halide, which is defined in this example as "one equivalent of alkyl halide."

[0482] 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 bromopropanol (3.2 g, 0.023 mol, 0.064 equiv.) was added dropwise at 0-5°C over 15-30 minutes. The reaction mixture was stirred at 0-5°C for 4-5 hours, then the temperature was allowed to rise to ambient temperature. The reaction was stirred at ambient temperature for 14-15 hours, after which the reaction mixture was a hazy solution.

[0483] The water content of the reaction mixture was reduced by azeotropic distillation of the solvent (approximately 10 mL). This volume of tert-amyl alcohol was added to the reaction mixture, and the distillation process was repeated three times. tert-amyl alcohol was added to make up the original reaction volume, and the resulting mixture was stirred at 50-60°C for 60-90 minutes, after which a clear solution was obtained.

[0484] 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) was added at 50-60°C. The temperature was raised to 94-98°C, and the reaction was stirred at this temperature for 48 hours, resulting in a clear brown solution. The solvent was removed under reduced pressure below 60°C, and the resulting residue was cooled to 25-30°C and 500 mL of acetone was added. 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 liquid was decanted from the solid, and acetone (500 mL) was added to the solid residue. The suspension was stirred at 25-30°C for 30-60 minutes, after which the stirring was stopped, the suspension was allowed to settle for 30-60 minutes, and the supernatant was decanted from the settled solids. This process of stirring, settling, and decanting the suspension was repeated several times until the 1-bromooctadecane and 1-bromooctane in the supernatant was less than 0.5% as determined by GC analysis.

[0485] The remaining solvent was removed under reduced pressure below 35°C. The solid product was further dried at below 35°C for 8-10 hours to yield 40.6 g of QPEI product as a light brown solid. The bromine content was determined to be approximately 23% as measured by AgNO titration. The theoretical mole percentages for reaction with 1-bromopropanol and a 75 / 25 mixture of 1-bromooctadecane and 1-bromooctane are 6.4% and 93.6%, respectively.

[0486] Example 33. Compound 33-1 [ka]

[0487] A 0.5 L four-neck round-bottom flask was fitted with a dropping funnel, a condenser, a water bath, and a mechanical stirrer. The flask was flushed with nitrogen gas and the reaction was carried out under a stream of nitrogen gas.

[0488] Ten grams of 25 kDa hyperbranched PEI (0.180 moles of amine content with an approximately 1:1:1 ratio of primary to secondary to tertiary amines) was added to the flask and stirred at 160-180 RPM. Note that theoretically, the 0.180 moles of nitrogen content at this ratio of primary, secondary, and tertiary amines can react with 0.120 moles of caprolactone ("1 equivalent of caprolactone" in this example) and 0.360 moles of 1-bromohexane ("1 equivalent of 1-bromohexane" in this example).

[0489] Water (10 g) was added to the flask along with tert-amyl alcohol (50 ml) and the resulting solid suspension was cooled to 0-5°C.

[0490] Caprolactone (2.65 g, 0.0238 mol, 0.2 equiv.) was added dropwise over 15-30 min at 0-5° C. The resulting mixture was stirred at 0-5° C. for 4-5 h. The temperature was raised to 25-30° C. and the reaction was stirred at this temperature for 14-15 h to give a hazy solution.

[0491] The tert-amyl alcohol was distilled off to azeotropically remove water from the reaction mixture, and fresh tert-amyl alcohol was added to replace the evaporated solvent. The reaction temperature was increased to 50-60°C, and the reaction was stirred for 60-90 minutes to obtain a clear solution. 1-Bromohexane (153.2 g, 0.928 mol, 2.6 equiv.) was added. The resulting reaction mixture was stirred at 50-60°C for 15-30 minutes, and then the temperature was increased to 94-98°C. The reaction was stirred at this temperature for 48 hours to obtain a solid suspension.

[0492] The reaction 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 liquid was decanted from the settled solid, and fresh diethyl ether (100 ml) was added. This process of stirring, settling, and decanting the suspension was repeated several times until the 1-bromohexane content in the decanted liquid was less than 0.5%, as determined by GC analysis.

[0493] The remaining solvent was removed under reduced pressure below 35°C. The crude solid product was further dried below 35°C for 10-12 hours to give the QPEI product (32 g) as a beige solid. The water content was determined to be 1200 ppm as measured by Karl Fischer analysis. The bromine content was determined to be approximately 35% as measured by AgNO titration.

[0494] The theoretical mole percentages of PEI reaction with caprolactone and 1-bromohexane are about 7% and about 93%, respectively, assuming that caprolactone reacts primarily with primary amines.

[0495] Example 34. Additional QPEI Compounds The following compounds were prepared using procedures similar to those in the examples above. [ka] [Table 17]

[0496] Example 35. Antibacterial activity study Minimum inhibitory concentration (MIC) The antibacterial efficacy of the tested compounds was investigated using a standard broth microdilution method. Serial two-fold dilutions were prepared for each compound at concentrations ranging from 100 μM to 0.8 μM in sterile MH broth in flat 96-well plates. The ONC for each bacterial strain was adjusted to achieve a standard bacterial concentration (5 × 10 5 The CFU / mL was obtained and 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 as a vehicle-only control, and positive (bacteria only) and negative (MH medium only) controls were included for each bacterial strain. MIC breakpoint 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 absorbance was measured at 570 nm (plate reader). The MIC is defined as the lowest concentration of compound that inhibits growth. MH medium was used as a negative control, and bacteria alone was used as a positive control on each plate for all compounds tested. Serial two-fold dilutions were performed by mixing 50 μL of the highest concentration (x2) into rows A through H containing 50 μL of sterile MH broth.

[0497] MIC data analysis Data were exported to Microsoft Excel and background normalized by subtracting OD570nm values ​​from medium-only wells (-VE control). MIC values ​​were determined by plotting OD570nm values ​​(Y) against the logarithmic concentration (X) of each compound. A modified Gompertz model was used to fit the data to obtain more accurate MICs. The mean OD570nm for each test compound concentration was fitted to a sigmoidal curve using a modified Gompertz function (y = A + Ce - e(B(xM))), and the minimum inhibitory concentration (MIC) was determined from the inflection point of the lower asymptote (GraphPad Prism 9.0). This was applied to the average of three biological replicates, each with four technical replicates (n = 12), for each dilution in each compound.

[0498] Minimum Lethal Concentration (MBC) Procedure To determine the MBC compound concentration, the breakpoint was estimated from the MIC curve. For all bacterial strains, overnight cultures were set up as described above. The next day, the overnight cultures were adjusted to 5 x 10 per mL. 5 A cell density of 1000 cells was obtained. Briefly, the cultures were adjusted to a McFarland standard (0.08–0.12) and diluted (1:150). The adjusted cultures were inoculated into 96-well plates containing 50 μL of sterile Mueller-Hinton broth (MHB) and two concentrations of each compound. MBC plates were incubated statically at 37°C for 24 hours. Sterile dH2O was used as a vehicle control, and positive (bacteria only) and negative (medium only) controls were also included in the assay. MBC cultures were serially diluted in 96-well plates and quantified by spot plating on Mueller-Hinton broth agar (MHA). MHA plates were incubated at 37°C for 24 hours and counted. Results are presented as CFU per mL.

[0499] Summary of results: [Table 18] [Table 19]

[0500] Compounds 25-1 (batches 105402 and 109634), 39637 (batches 105543 and 109466), 24-1 (batch 109590), 23-1 (batch 109770), and 26-1 (batch 109781) showed strong antibacterial activity against the Gram-positive species Enterococcus faecalis and Staphylococcus aureus.

[0501] For Gram-negative species (Klebsiella pneumonia and Pseudomonas aeruginosa), three compounds, namely, compounds 22-1 (batch 105159), 22-1 (batch 99367), and 24-1 (batch 109590), were able to show inhibitory effects within the investigated concentration range.

[0502] Compounds 39637 (batches 105543 and 109466), 24-1 (batch 109590), and 23-1 (batch 109770) inhibited Staphylococcus Aureus at concentrations ranging from 1.57 μM to 6.25 μM.

[0503] Of all the compounds tested, the most effective MICs and MBCs were lower in Gram-positive bacteria, but appear to be broad-spectrum active in Gram-negative bacteria at much higher concentrations.

[0504] Compound 22-1 (batches 105159 and 99367) exhibited the most potent MBC inhibition profile across all bacterial strains. The MBC values ​​clearly show inhibition of all strains at relatively low concentrations.

[0505] Of all the compounds tested above, the following showed the lowest antibacterial activity: compounds 40840 (batch 110435), 40598 (batch 109448), 30-1 (batch 109666), 28-1 (batch 109831), and 40597 (batch 109444). Compound 27-1 (batch 110417) showed low antibacterial efficacy via MIC, but inhibited 5 of 7 strains at MBC of 6.25 μM.

[0506] Additional compounds were tested and obtained MIC values ​​against the same bacteria shown in Tables 16 and 17 (see Table 18). ****: MIC of QPEI ≦12.5 μM for all bacteria tested; ***: MIC of QPEI >12.5 μM for more than 50% of bacteria tested and MIC of QPEI ≦50 μM; **: MIC of QPEI >12.5 μM for less than 50% of bacteria tested and MIC of QPEI ≦50 μM; *: MIC of QPEI >100 μM for all bacteria tested. [Table 20]

[0507] References: __________ 1 Ellingson, KD, et al. (2020). “Urban Hospital Study-Antimicrobial Surface Coating.” Clinical Infectious Diseases, 71(8):1807-1813. 2 Jarach, N., et al., (2020). “Polymers in the Medical Antiviral Front-Line”. Polymers, 12(8):1727. 3 THE MERCK MANUAL OF DIAGNOSIS AND THERAPY,(2011).19 thEdition, published by Merck Sharp & Dohme Corp., (ISBN 978 - 0 - 911910 - 19 - 3). 4 THE ENCYCLOPEDIA OF MOLECULAR CELL BIOLOGY AND MOLECULAR MEDICINE, edited by Robert S. Porter et al., published by Blackwell Science Ltd., 1999 - 2012 (ISBN 9783527600908). 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). 6 IMMUNOLOGY, (2006). Published by Werner Luttmann, Elsevier. 7 JANEWAY’S IMMUNOBIOLOGY, (2014). Edited by Kenneth Murphy, Allan Mowat, Casey Weaver, Taylor & Francis Limited, (ISBN 0815345305, 9780815345305). 8 LEWIN’S GENES XI, (2014). Published by Jones & Bartlett Publishers (ISBN - 1449659055). 9 Michael Richard Green and Joseph Sambrook, (2012). MOLECULAR CLONING: A LABORATORY MANUAL, 4th ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y., USA (ISBN 1936113414). 10Davis et al.,(2012).BASIC METHODS IN MOLECULAR BIOLOGY,Elsevier Science Publishing,Inc.,New York,USA(ISBN 044460149X). 11 LABORATORY METHODS IN ENZYMOLOGY:DNA,(2013).Jon Lorsch(ed.) Elsevier(ISBN 0124199542). 12 CURRENT PROTOCOLS IN MOLECULAR BIOLOGY(CPMB),(2014).Frederick M.Ausubel(ed.),John Wiley and Sons(ISBN 047150338X,9780471503385). 13 CURRENT PROTOCOLS IN PROTEIN SCIENCE(CPPS),(2005).John E.Coligan(ed.),John Wiley and Sons,Inc. 14 CURRENT PROTOCOLS IN IMMUNOLOGY(CPI)(2003).Coligan,J.E.,et al.,(eds.) John Wiley and Sons,Inc.(ISBN 0471142735,9780471142737). 15 Ikonen,N.,et al.,(2018).“Deposition of respiratory virus pathogens on frequently touched surfaces at airports.”BMC Infectious Diseases,18(437):1-8. 16Geczi, Z., et al., (2018). “Antimicrobial Silver-Polyethyleneimine Polylactic Acid Polymer Composite Film for Coating Methacrylate-Based Denture Surfaces.” J. of Nanomaterials, 2018(6): 19. 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. 18 Xue, Y. and Xiao, H. (2015). “Antibacterial / Antiviral Property and Mechanism of Dual-Functional Quaternized Pyridinium-Type Copolymer.” Polymers, 7(11): 2290 - 2303. 19 U.S. Patent No. 5,783,502, “Virus Inactivating Coatings.” (Issued on July 21, 1998). 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. 21Chung, S., et al., (2016). “Antimicrobial Nanostructural Polyurethane Scaffolds.” Ch.17, ADVANCES IN POLYURETHANE BIOMATERIALS, Cooper S.L. and Guan, J. (eds.), Elsevier Ltd. 22 Park, D., et al., (2013). “Antiviral and Antibacterial Polyurethanes of Various Modalities.” Appl. Biochem. Biotechnol., 169: 1134 - 1146. 23 Gao, B., et al., (2007). “Studies on the Preparation and Antibacterial Properties of Quaternized Polyethyleneimine.” J. Biomaterials Science, Polymer Edition, 18(5): 531 - 544. 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. 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. 26 Id.

[0508] All patents and other publications, including references, issued patents, published patent applications, and co-pending patent applications, cited throughout this application are expressly incorporated herein by reference for the purpose of describing and disclosing, for example, the methodology described in such publications, that might be used in connection with the technology described herein. These publications are provided solely for their disclosure prior to the filing date of this application. Nothing in this regard should be construed as an admission that the applicant is not entitled to antedate such disclosure by virtue of prior invention or for any other reason. All statements as to a date or representation as to the contents of these documents are based on the information available to the applicant and do not constitute any admission as to the accuracy of the dates or contents of these documents.

[0509] The foregoing written specification is deemed sufficient to enable one skilled in the art to practice the present aspects and embodiments. The present aspects and embodiments are not limited in scope by the provided examples, as the examples are intended to be merely illustrative of an embodiment; other functionally equivalent embodiments are within the scope of the present disclosure. Various modifications, in addition to those shown and described herein, will be apparent to those skilled in the art from the foregoing description and are encompassed within the scope of the appended claims. The advantages and objectives described herein are not necessarily encompassed by each embodiment. Those skilled in the art will recognize, or be able to ascertain using no more than routine experimentation, many equivalents to the specific embodiments described herein. Such equivalents are intended to be encompassed by the following claims.

Claims

1. 1. An antimicrobial composition comprising an oil-in-water emulsion, said oil-in-water emulsion comprising: (i) an oil phase, a first adduct of a first multifunctional crosslinker and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first multifunctional crosslinker; optionally a polyol, a polyethyleneimine intermediate or a second adduct of said polyethyleneimine intermediate and a second multifunctional crosslinker; and an oil phase optionally comprising a third multifunctional crosslinker; (ii) an aqueous phase comprising a water-soluble polymer; the polyethyleneimine intermediate comprises an optionally substituted hydroxyalkylene functional group that reacts with the first adduct and, if present, the second multifunctional crosslinker; An antimicrobial composition wherein the nitrogen atoms present in said polyethyleneimine intermediate are at least partially quaternized.

2. 10. The antimicrobial composition of claim 1, wherein the water-soluble polymer is crosslinked with (a) the first multifunctional crosslinker incorporated in the first adduct, (b) the second multifunctional crosslinker, if present, incorporated in the second adduct, (c) the third multifunctional crosslinker, if present, or (d) any combination of two or more thereof.

3. The first quaternary ammonium salt is 【Chemical 1】 wherein: R １ But -(C ８ -C ３０ alkyl), -(C ８ -C ３０ heteroalkyl), -(C ８ -C ３０ heteroalkyl)-(C ６ -C １０ aryl), -(C ６ -C １０ aryl), -(C ６ -C １０ aryl)-(C ８ -C ３０ alkyl), -(C ６ -C １０ aryl)-(C ８ -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—, —(C ８ -C ３０ heteroalkyl), -(C ８ -C ３０ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl)-(C ８ -C ３０ heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si; R ２ But -(C １ -C ４ alkyl), -(C １ -C ４ heteroalkyl), -(C １ -C ４ heteroalkyl)-(C ６ -C １０ aryl), -(C ６ -C １０ aryl), -(C ６ -C １０ aryl)-(C １ -C ４ alkyl), -(C ６ -C １０ aryl)-(C １ -C ４ 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, -(C １ -C ４ heteroalkyl), -(C １ -C ４ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl)-(C １ -C ４ heteroalkyl) has 1 to 2 heteroatoms independently selected from O, S, and Si; R ３ But -(C １ -C ３０ alkyl), -(C １ -C ３０ heteroalkyl), -(C １ -C ３０ heteroalkyl)-(C ６ -C １０ aryl), -(C ６ -C １０ aryl), -(C ６ -C １０ aryl)-(C １ -C ３０ alkyl), -(C ６ -C １０ aryl)-(C １ -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, -(C １ -C ３０ heteroalkyl), -(C １ -C ３０ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl)-(C １ -C ３０ heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si; A is -(C ３ -C ２０ alkylene)-, -(C ３ -C ２０ heteroalkylene)-, -(C ６ -C １０ arylene)-(C ３ -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 -(C ３ -C ２０ heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; ３ -C ２０ alkylene)- and -(C ３ -C ２０ heteroalkylene)- is -(C ６ -C １０ aryl)-(C １ -C ３ alkyl), -(C ６ -C １０ aryl)-(C １ -C ３ heteroalkyl), -(C １ -C ３ alkyl)-(C ６ -C １０ aryl), -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl); Each R ｍ , R ｎ , R ｐ , and R ｑ independently H and C １ -C ４ alkyl, 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)—; W １１ , W ２１ , W ３１ , and W ４１ are independently 5- to 6-membered cycloalkyl, C ６ -C １０ selected from aryl, 5- to 6-membered heterocycloalkyl, and 5- to 6-membered heteroaryl, wherein said heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and said heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si; x10 is an integer from 1 to 30, y10 is an integer from 0 to 29, and 8≦(x10+y10)≦30; x11 is an integer of 1 to 30, y11 is an integer of 0 to 29, and 8≦(x11+y11)≦30; x20 is an integer of 1 to 4, y20 is an integer of 0 to 3, and x20+y20≦4; x21 is an integer of 1 to 4, y21 is an integer of 0 to 3, and x21+y21≦4; x30 is an integer of 1 to 30, y30 is an integer of 0 to 29, and x30+y30≦30; x31 is an integer of 1 to 30, y31 is an integer of 0 to 29, and x31+y31≦30; x40 is an integer from 1 to 19, y40 is an integer from 1 to 19, and 3≦(x40+y40)≦20; x41 is an integer of 1 to 20, y41 is an integer of 0 to 19, and 3≦(x41+y41)≦20; --OH、-NHR ４ ,-SH,-CO ２ H、-C(O)NHR ４ ,-C(S)NHR ４ 、 【Chemistry 2】 is selected from the group consisting of Each R ４ are independently H, -(C ６ -C １０ aryl)-(C １ -C ３ alkyl), -(C ６ -C １０ aryl)-(C １ -C ３ heteroalkyl), -(C １ -C ３ alkyl)-(C ６ -C １０ aryl), -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl), and ６ -C １０ aryl)-(C １ -C ３ heteroalkyl) and -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si; X － 3. The antimicrobial composition of claims 1 and 2, wherein is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, borate, or an organically substituted derivative of any of the foregoing.

4. R １ But -(C １２ -C ３０ alkyl), -(C １２ -C ３０ heteroalkyl), -(C １２ -C ３０ alkyl)-(C ６ -C １０ aryl), -(C １２ -C ３０ heteroalkyl)-(C ６ -C １０ aryl), -(C ６ -C １０ aryl)-(C １２ -C ３０ alkyl), and -(C ６ -C １０ aryl)-(C １２ -C ３０ heteroalkyl), １２ -C ３０ heteroalkyl), -(C １２ -C ３０ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl)-(C １２ -C ３０ 4. The antimicrobial composition of claim 3, wherein the heteroalkyl has 1 to 4 heteroatoms independently selected from O, S, and Si.

5. R ３ But -(C １ -C ４ alkyl), -(C １ -C ４ heteroalkyl), -(C １ -C ４ alkyl)-(C ６ -C １０ aryl), -(C １ -C ４ heteroalkyl)-(C ６ -C １０ aryl), -(C ６ -C １０ aryl)-(C １ -C ４ alkyl), and -(C ６ -C １０ aryl)-(C １ -C ４ heteroalkyl), １ -C ４ heteroalkyl), -(C １ -C ４ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl)-(C １ -C ４ 5. The antimicrobial composition of claim 3, wherein the heteroalkyl has 1 to 4 heteroatoms independently selected from O, S, and Si.

6. R ２ and R ３ The antimicrobial composition according to any one of claims 3 to 5, wherein is methyl.

7. A is -(CH ２ ) ｍ - or - (CH ２ CHR ５ -O-) ｎ CH ２ CHR ５ -, wherein m is an integer from 2 to 20, n is 0, 1, 2, 3, 4, or 5, and each R ５ are independently H, -(C ６ -C １０ aryl)-(C １ -C ３ alkyl), -(C ６ -C １０ aryl)-(C １ -C ３ heteroalkyl), -(C １ -C ３ alkyl)-(C ６ -C １０ aryl), -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl), and ６ -C １０ aryl)-(C １ -C ３ heteroalkyl) and -(C １ -C ３ heteroalkyl)-(C ６ -C １０ 7. The antimicrobial composition of claim 3, wherein (aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si.

8. Each R ５ The antimicrobial composition of claim 7 , wherein is independently H or methyl.

9. The first quaternary ammonium salt is 【Chemistry 3】 The antimicrobial composition according to any one of claims 1 to 8, which is a combination of two or more thereof.

10. 10. The antimicrobial composition of any one of claims 1 to 9, wherein the first quaternary ammonium salt is present in the oil phase in an amount of about 1 wt % to about 50 wt %, based on the dry weight of the oil phase.

11. 11. The antimicrobial composition of any one of claims 1 to 10, wherein the first quaternary ammonium salt is present in the oil phase in an amount of about 5% to about 25% by weight, based on the dry weight of the oil phase.

12. 13. The antimicrobial composition of any one of claims 1 to 12, wherein the first multifunctional crosslinker incorporated in the first adduct is present in the oil phase in an amount of from about 2% to about 25% by weight based on the dry weight of the oil phase.

13. 14. The antimicrobial composition of any one of claims 1 to 13, wherein the first multifunctional crosslinker incorporated in the first adduct is present in the oil phase in an amount of from about 5% to about 20% by weight based on the dry weight of the oil phase.

14. 15. The antimicrobial composition of any one of claims 1 to 14, wherein the second multifunctional crosslinker incorporated in the second adduct is present in the oil phase in an amount of from about 0.1 wt % to about 10 wt %, based on the dry weight of the oil phase.

15. 16. The antimicrobial composition of any one of claims 1 to 15, wherein the second multifunctional crosslinker incorporated in the second adduct is present in the oil phase in an amount of from about 2% to about 8% by weight based on the dry weight of the oil phase.

16. 17. The antimicrobial composition of any one of claims 1 to 16, wherein the third multifunctional crosslinker is present in the oil phase in an amount of from about 0.1 wt % to about 20 wt %, based on the dry weight of the oil phase.

17. 18. The antimicrobial composition of any one of claims 1 to 17, wherein the third multifunctional crosslinker is present in the oil phase in an amount of from about 2% to about 15% by weight, based on the dry weight of the oil phase.

18. 18. The antimicrobial composition of any one of claims 1 to 17, wherein the first multifunctional crosslinker is a first polyisocyanate, the second multifunctional crosslinker, if present, is a second polyisocyanate, and the third multifunctional crosslinker, if present, is a third polyisocyanate, and the first polyisocyanate, second polyisocyanate, and third polyisocyanate are different.

19. 18. The antimicrobial composition of any one of claims 1 to 17, wherein the first multifunctional crosslinker is a first polyisocyanate, the second multifunctional crosslinker, if present, is a second polyisocyanate, and the third multifunctional crosslinker, if present, is a third polyisocyanate, and the first polyisocyanate, second polyisocyanate, and third polyisocyanate are the same.

20. 20. The antimicrobial composition of claim 18 or 19, wherein the first, second, and third polyisocyanates each have an average isocyanate functionality of 2 to 5.

21. 21. The antimicrobial composition of claim 20, wherein the first, second, and third polyisocyanates each have an average isocyanate functionality of 3 to 4.

22. 22. The antimicrobial composition of any one of claims 18-21, wherein each of the first, second, and third polyisocyanates 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), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

23. 22. The antimicrobial composition of any one of claims 18-21, wherein each of the first, second, and third polyisocyanates is independently selected from the group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T-series polyisocyanates, and LUPRANATE® M-series polyisocyanates.

24. 24. The antimicrobial composition of any one of claims 18 to 23, wherein the first adduct has an average isocyanate functionality of 2 to 3.

25. 25. The antimicrobial composition of claim 24, wherein the first adduct has an average isocyanate functionality of from about 2.05 to about 2.

3.

26. 26. The antimicrobial composition of any one of claims 18 to 25, wherein reactive isocyanate functional groups on the first adduct are blocked with a blocking agent.

27. 27. The antimicrobial composition of claim 26, wherein the blocking agent is selected from the group consisting of oximes, phenols, malonates, alcohols, lactams, dicarbonyl compounds, hydroxamates, bisulfite adducts, hydroxylamines, esters of p-hydroxybenzoic acid, and salicylic acid.

28. 28. The antimicrobial composition of 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 of any one of claims 25 to 28, further comprising a deblocking agent.

30. 30. The antimicrobial composition of claim 29, wherein the deblocking agent is selected from the group consisting of organotins, organobismuths, and tertiary amines.

31. 31. The antimicrobial composition of any one of claims 1 to 30, wherein the first adduct is present in the oil phase in an amount of from about 5% to about 70% by weight based on the dry weight of the oil phase.

32. 32. The antimicrobial composition of any one of claims 1 to 31, wherein the second adduct is present in the oil phase in an amount of from about 1% to about 30% by weight based on the dry weight of the oil phase.

33. 33. The antimicrobial composition of any one of claims 1 to 32, wherein the second adduct is present in the oil phase in an amount of from about 3% to about 15% by weight based on the dry weight of the oil phase.

34. 34. The antimicrobial composition of any one of claims 1 to 33, wherein the oil phase further comprises an organic solvent or diluent.

35. 35. The antimicrobial composition of claim 34, wherein the organic solvent or diluent in the oil phase is water-miscible.

36. 36. The antimicrobial composition of claim 34 or 35, wherein the organic solvent or diluent is acetone.

37. 37. The antimicrobial composition of any one of claims 34 to 36, wherein the organic solvent or diluent is present in the oil phase in an amount of from about 5% to about 35% by weight based on the weight of the oil phase.

38. 38. The antimicrobial composition of any one of claims 34 to 37, wherein the organic solvent or diluent is present in the oil phase in an amount of about 10% to about 30% by weight, based on the weight of the oil phase.

39. 39. The antimicrobial composition of any one of claims 1 to 38, wherein the polyol, if present, 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.

40. 40. The antimicrobial composition of 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. 41. The antimicrobial composition of claim 39 or 40, wherein the polyol has a weight average molecular weight of about 300 to about 3000.

42. 42. The antimicrobial composition of any one of claims 39 to 41, wherein the polyol has a weight average molecular weight of about 400 to about 2000.

43. 43. The antimicrobial composition of any one of claims 39 to 42, wherein the polyol has a weight average molecular weight of about 600 to about 1500.

44. 44. The antimicrobial composition of any one of claims 1 to 43, wherein the polyol is present in the oil phase in an amount of from about 1% to about 40% by weight based on the dry weight of the oil phase.

45. 45. The antimicrobial composition of any one of claims 1 to 44, wherein the polyol is present in the oil phase in an amount of from about 5% to about 25% by weight based on the dry weight of the oil phase.

46. 46. ​​The antimicrobial composition of 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 intermediates, copolymers of two or more thereof, copolymers of one or more of them with polyvinylpyrrolidone poly(glycidyl acrylate) or poly(glycidyl methacrylate), and combinations or blends of two or more thereof.

47. 46. ​​The antimicrobial composition of any one of claims 1 to 45, wherein the water-soluble polymer is hydroxyethyl cellulose or a hydrophobically modified derivative thereof.

48. 46. ​​The antimicrobial composition of any one of claims 1 to 45, wherein the water-soluble polymer is a polyethyleneimine intermediate.

49. 49. The antimicrobial composition of any one of claims 1 to 48, wherein the water-soluble polymer is present in the aqueous phase in an amount of from about 0.5% to about 15% by weight of the dry weight of the oil phase.

50. 50. The antimicrobial composition of any one of claims 1 to 49, wherein the water-soluble polymer is present in the aqueous phase in an amount of from about 3% to about 12% by weight of the dry weight of the oil phase.

51. 51. The antimicrobial composition of any one of claims 1 to 50, wherein the water-soluble polymer is present in the aqueous phase in an amount of about 5% to about 10% by weight of the dry weight of the oil phase.

52. 52. The antimicrobial composition of any one of claims 1 to 51, wherein the aqueous phase further comprises a surfactant.

53. 53. The antimicrobial composition of claim 52, wherein the surfactant is a non-ionic surfactant.

54. 54. The antimicrobial composition of claim 53, wherein the nonionic surfactant has an average HLB (hydrophile-lipophile balance) value of about 12 to about 15.

55. 55. The antimicrobial composition of claim 53 or 54, wherein the nonionic surfactant is selected from TRITON® X-114 ((1,1,3,3-tetramethylbutyl)phenyl-polyethylene glycol), SILWET™ L-7604 (siloxane polyalkylene oxide copolymer), and combinations thereof.

56. 56. The antimicrobial composition of any one of claims 52 to 55, wherein the surfactant is present in the aqueous phase in an amount of from about 0.05% to about 2% by weight based on the dry weight of the oil phase.

57. 57. The antimicrobial composition of any one of claims 52 to 56, wherein the surfactant is present in the aqueous phase in an amount of about 0.1% to about 1% by weight based on the dry weight of the oil phase.

58. 58. The antimicrobial composition of any one of claims 1 to 57, wherein the aqueous phase further comprises an antifoaming or anti-foaming agent.

59. 59. The antimicrobial composition of claim 58, wherein the antifoam agent is FOAMSTAR® ST 2410 (a star polymer-based antifoam agent).

60. 57. The antimicrobial composition of any one of claims 1 to 56, wherein a random polymer or interpenetrating polymer network is produced from the random polymerization / crosslinking of the first adduct, the polyethyleneimine intermediate or the second adduct, if present, the polyol, the water-soluble polymer, if reactive, and the third multifunctional crosslinker, if present.

61. the oil phase contains the first multifunctional crosslinker and the second quaternary ammonium salt 【Chemistry 4】 wherein: R １ａ , R ２ａ , and R ３ａ are each independently methyl or ethyl; A １ But -(C ３ -C ２０ alkylene)-, -(C ３ -C ２０ heteroalkylene)-, -(C ６ -C １０ arylene)-(C ３ -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 -(C ３ -C ２０ heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; ３ -C ２０ alkylene)- and -(C ３ -C ２０ heteroalkylene)- is -(C ６ -C １０ aryl)-(C １ -C ３ alkyl), -(C ６ -C １０ aryl)-(C １ -C ３ heteroalkyl), -(C １ -C ３ alkyl)-(C ６ -C １０ aryl), -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl); Each R ｍ１ , R ｎ１ , R ｐ１ , and R ｑ１ independently H and C １ -C ４ alkyl, W ４２ is selected from —C(O)—, —C(O)O—, —OC(O)—, —C(O)NH—, and —NHC(O)—; W ４３ is 5- to 6-membered cycloalkyl, C ６ -C １０ selected from aryl, 5- to 6-membered heterocycloalkyl, and 5- to 6-membered heteroaryl, wherein said heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and said heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si; x42 is an integer from 1 to 19, y42 is an integer from 1 to 19, and 3≦(x42+y42)≦20; x43 is an integer of 1 to 20, y43 is an integer of 0 to 19, and 3≦(x43+y43)≦20; Y １ が、-OH、-NHR ４ａ ,-SH,-CO ２ H、-C(O)NHR ４ａ ,-C(S)NHR ４ａ 、 【Chemistry 5】 is selected from the group consisting of Each R ４ａ are independently H, -(C ６ -C １０ aryl)-(C １ -C ３ alkyl), -(C ６ -C １０ aryl)-(C １ -C ３ heteroalkyl), -(C １ -C ３ alkyl)-(C ６ -C １０ aryl), -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl), ６ -C １０ aryl)-(C １ -C ３ heteroalkyl) and -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si; X － is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, borate, or an organically substituted derivative of any of the foregoing.

62. the oil phase comprises a fourth multifunctional crosslinker and a second quaternary ammonium salt 【Chemistry 6】 wherein: R １ａ , R ２ａ , and R ３ａ are each independently methyl or ethyl; A １ But -(C ３ -C ２０ alkylene)-, -(C ３ -C ２０ heteroalkylene)-, -(C ６ -C １０ arylene)-(C ３ -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 -(C ３ -C ２０ heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; ３ -C ２０ alkylene)- and -(C ３ -C ２０ heteroalkylene)- is -(C ６ -C １０ aryl)-(C １ -C ３ alkyl), -(C ６ -C １０ aryl)-(C １ -C ３ heteroalkyl), -(C １ -C ３ alkyl)-(C ６ -C １０ aryl), -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl); Each R ｍ１ , R ｎ１ , R ｐ１ , and R ｑ１ independently H and C １ -C ４ alkyl, W ４２ is selected from —C(O)—, —C(O)O—, —OC(O)—, —C(O)NH—, and —NHC(O)—; W ４３ is 5- to 6-membered cycloalkyl, C ６ -C １０ selected from aryl, 5- to 6-membered heterocycloalkyl, and 5- to 6-membered heteroaryl, wherein said heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and said heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si; x42 is an integer from 1 to 19, y42 is an integer from 1 to 19, and 3≦(x42+y42)≦20; x43 is an integer of 1 to 20, y43 is an integer of 0 to 19, and 3≦(x43+y43)≦20; Y １ が、-OH、-NHR ４ａ ,-SH,-CO ２ H、-C(O)NHR ４ａ ,-C(S)NHR ４ａ 、 【Chemistry 7】 is selected from the group consisting of Each R ４ａ are independently H, -(C ６ -C １０ aryl)-(C １ -C ３ alkyl), -(C ６ -C １０ aryl)-(C １ -C ３ heteroalkyl), -(C １ -C ３ alkyl)-(C ６ -C １０ aryl), -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl), ６ -C １０ aryl)-(C １ -C ３ heteroalkyl) and -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si; X － is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, borate, or an organically substituted derivative of any of the foregoing.

63. 63. The antimicrobial composition of claim 62, wherein the fourth multifunctional crosslinker is different from the first multifunctional crosslinker, and, if present, the second multifunctional crosslinker, and, if present, the third multifunctional crosslinker.

64. 64. The antimicrobial composition of claim 62 or 63, wherein a fourth polyisocyanate is present in the oil phase in an amount of from about 0.1 wt % to about 15 wt %, based on the dry weight of the oil phase.

65. 65. The antimicrobial composition of any one of claims 62 to 64, wherein the fourth multifunctional crosslinker is a fourth polyisocyanate.

66. 66. The antimicrobial composition of claim 65, wherein the fourth polyisocyanate has an average isocyanate functionality of 2 to 5.

67. 67. The antimicrobial composition of claim 65 or 66, 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), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

68. 67. The antimicrobial composition of claim 65 or 66, wherein the fourth polyisocyanate is selected from the group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T-series polyisocyanates, and LUPRANATE® M-series polyisocyanates.

69. The second quaternary ammonium salt is 【Chemistry 8】 The antimicrobial composition of any one of claims 61 to 68, wherein

70. 70. The antimicrobial composition of 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. 71. The antimicrobial composition of 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% to about 10% by weight, based on the dry weight of the oil phase.

72. 72. The antimicrobial composition of any one of claims 61 to 71, wherein the third adduct has an average isocyanate functionality of 2 to 3.

73. 73. The antimicrobial composition of any one of claims 61 to 72, wherein the third adduct has an average isocyanate functionality of from about 2.05 to about 2.

3.

74. 74. The antimicrobial composition of any one of claims 61 to 73, wherein the third adduct is present in the oil phase in an amount of from about 2% to about 30% by weight based on the dry weight of the oil phase.

75. 75. The antimicrobial composition of any one of claims 61 to 74, wherein reactive isocyanate functional groups on the third adduct are blocked with a blocking agent.

76. 76. The antimicrobial composition of claim 75, wherein the blocking agent is selected from the group consisting of oximes, phenols, malonates, alcohols, lactams, dicarbonyl compounds, hydroxamates, bisulfite adducts, hydroxylamines, esters of p-hydroxybenzoic acid, and salicylic acid.

77. 77. The antimicrobial composition of claim 76, 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.

78. 75. The antimicrobial composition of any one of claims 61 to 74, wherein a random polymer or interpenetrating polymer network is produced from random polymerization / crosslinking of the first adduct, the polyethyleneimine intermediate or the second adduct, the third adduct, the polyol, if present, the water-soluble polymer, if reactive, and the third multifunctional crosslinker, if present.

79. The oil phase is HO—(C ｎ H ２ｎ )-OH and HO-(C ｎ H ２ｎ－２ 78. The antimicrobial composition of any one of claims 1-59 or 61-77, further comprising a chain extender selected from the group consisting of: —NH—, ...

80. 80. The antimicrobial composition of claim 79, wherein the chain extender is propanediol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexanedimethanol, or a combination of two or more thereof.

81. 81. The antimicrobial composition of 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. 82. The antimicrobial composition of any one of claims 79 to 81, wherein the chain extender is present in the oil phase in an amount of from about 0.5% to about 10% by weight based on the dry weight of the oil phase.

83. 83. The antimicrobial composition of any one of claims 79-82, wherein a random polymer or interpenetrating polymer network is produced from random polymerization / crosslinking of the first adduct, the polyethyleneimine intermediate or the second adduct, if present, the third adduct, if present, the polyol, the chain extender, the water-soluble polymer, if reactive, and the third multifunctional crosslinker, if present.

84. 84. The antimicrobial composition of any one of the preceding claims, wherein the polyethyleneimine intermediate is present in the oil phase in an amount of from about 0.1% to about 50% by weight based on the dry weight of the oil phase.

85. The hydroxyalkylene functional group is —N ＋ (R ２０ ) ３ X － , -(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ alkoxy), -(C １ -C ６ alkoxy), -(C １ -C ６ alkyl) optionally substituted with -(C ６ -C １０ aryl), and C optionally substituted with a substituent selected from carboxy １ -C ６ and each R ２０ But independently, C １ -C １８ alkyl; C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N １ -C １８ Heteroalkyl, and -(C １ -C ６ alkyl), -(C １ -C ６ alkoxy), —C(O)O—(C １ -C ６ alkyl), —C(O)NH(C １ -C ６ alkyl), —C(O)N(C １ -C ６ alkyl) ２ , or —OC(O)—(C １ -C ６ C optionally substituted with alkyl ６ -C １０ aryl, and each X － is independently selected from the group consisting of acetate, halides, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

86. 86. The antimicrobial composition of any one of claims 1 to 85, wherein the hydroxyalkylene functional group is hydroxyethylene, hydroxypropylene, hydroxybutylene, or an oligomer thereof.

87. The polyethyleneimine intermediate comprises the reaction product of a polyethyleneimine, a monoepoxide, and a reagent comprising an alkylating agent, the monoepoxide being -(C ６ -C １０ aryl), and -(C optionally substituted with hydroxy １ -C ６ Alkoxy), C １ -C ６ Alkoxy, C １ -C ６ C optionally substituted with alkyl ６ -C １０ C optionally substituted with a substituent selected from aryl and carboxy １ -C ６ 85. The antimicrobial composition of any one of claims 1 to 84, optionally substituted with alkyl.

88. The monoepoxide is C １ -C ６ 88. The antimicrobial composition of claim 87, which is an alkyl epoxide.

89. Said C １ -C ６ 89. The antimicrobial composition of claim 88, wherein the alkyl epoxide is selected from the group consisting of propyl epoxide, butyl epoxide, and hexyl epoxide.

90. The polyethyleneimine intermediate comprises the reaction product of a polyethyleneimine, a monoepoxide, and optionally a reagent comprising an alkylating agent, wherein the monoepoxide is -(C １ -C ６ alkyl)-N ＋ (R ２０ ) ３ X － and each R ２０ But independently, C １ -C １８ alkyl; C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N １ -C １８ Heteroalkyl, and -(C １ -C ６ alkyl), -(C １ -C ６ alkoxy), —C(O)O—(C １ -C ６ alkyl), —C(O)NH(C １ -C ６ alkyl), —C(O)N(C １ -C ６ alkyl) ２ , or —OC(O)—(C １ -C ６ C optionally substituted with alkyl ６ -C １０ aryl, and each X － is independently selected from the group consisting of acetate, halides, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

91. The alkylating agent may comprise one or more R ２１ -LG, wherein each R ２１ are independently —OH, —(C １ -C ６ alkoxy), carboxy, -(C ６ -C １０ aryl), —C(O)O(C １ -C ６ alkyl), —C(O)—(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ C optionally substituted with a substituent selected from １ -C ６ 91. The antimicrobial composition of any one of claims 87 to 90, wherein each LG is selected from alkyl, and each LG is a leaving group.

92. 92. The antimicrobial composition of claim 91, wherein the alkylating agent is a benzyl halide or a hexyl halide.

93. 85. The antimicrobial composition of any one of claims 1 to 84, wherein the polyethyleneimine intermediate comprises the reaction product of a reagent comprising polyethyleneimine and a haloalkanol.

94. The haloalkanol is X ３０ -(C ２ -C ６ alkylene)-OH, wherein X ３０ is Cl, Br, or I.

95. 95. The antimicrobial composition of any one of claims 87-94, wherein the reagent for the reaction product included in the polyethyleneimine intermediate further comprises a monoisocyanate.

96. The monoisocyanate may comprise one or more R ３０ -NCO, wherein each R ３０ are independently: (1) halogen, —SiR ａ (OR ｂ ) (OR ｃ ), and -(C ６ -C １０ C optionally substituted with 1 to 3 substituents independently selected from ６ -C ２０ alkyl, and (2) halogen, -(C １ -C ６ alkyl), and —SiR ａ (OR ｂ ) (OR ｃ C optionally substituted with 1 to 3 substituents independently selected from ６ -C １０ aryl, wherein each R ａ But independently, C １ -C ６ alkyl, and each R ｂ and each R ｃ are independently -(C １ -C ６ alkyl) and -Si(C １ -C ６ alkyl) ３ 96. The antimicrobial composition of claim 95, selected from:

97. 97. The antimicrobial composition of claim 95 or 96, wherein the monoisocyanate comprises octyl isocyanate, octadecyl isocyanate, or a combination thereof.

98. 98. The antimicrobial composition of any one of claims 87 to 97, wherein the polyethyleneimine has a molecular weight of from about 300 to about 270,000 daltons.

99. 99. The antimicrobial composition of any one of claims 87 to 98, wherein the polyethyleneimine has a molecular weight of about 10,000 to about 200,000 daltons.

100. 100. The antimicrobial composition of any one of claims 87 to 99, wherein the polyethyleneimine has a molecular weight of about 25,000 to about 120,000 daltons.

101. 101. The antimicrobial composition of any one of claims 87 to 100, wherein the polyethyleneimine is branched.

102. 101. The antimicrobial composition of any one of claims 87 to 100, wherein the polyethyleneimine is hyperbranched.

103. 103. The antimicrobial composition of any one of claims 87-102, wherein the polyethyleneimine has a ratio of primary to secondary to tertiary amines of from about 1:2:1 to about 1:1:

1.

104. 103. The antimicrobial composition of any one of claims 87-102, wherein the polyethyleneimine has a ratio of primary to secondary to tertiary amines of about 1:1:0.

7.

105. The polyethyleneimine intermediate is 【Chemistry 9】 or a copolymer of any two or more thereof, wherein: Each Y ３ are independently H or -O-Y ２ and all Y ３ But it cannot be H, Each Y ２ are independently H or —C(O)—NHR ３０ and all Y ２ is —C(O)—NHR ３０ It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C ２ -C ６ alkylene)-, Each R １０ are independently hydrogen; ＋ (R ２０ ) ３ X － , -(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ alkoxy), -(C １ -C ６ alkoxy), -(C １ -C ６ alkyl) optionally substituted with -(C ６ -C １０ aryl), and C optionally substituted with a substituent selected from carboxy １ -C ６ alkyl, and each R ２０ But independently, C １ -C １８ alkyl; C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N １ -C １８ Heteroalkyl, and -(C １ -C ６ alkyl), -(C １ -C ６ alkoxy), —C(O)O—(C １ -C ６ alkyl), —C(O)NH(C １ -C ６ alkyl), —C(O)N(C １ -C ６ alkyl) ２ , or —OC(O)—(C １ -C ６ C optionally substituted with alkyl ６ -C １０ aryl; Each R ２１ are independently —OH, —(C １ -C ６ alkoxy), carboxy, -(C ６ -C １０ aryl), —C(O)O(C １ -C ６ alkyl), —C(O)—(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ C optionally substituted with a substituent selected from １ -C ６ alkyl, Each R ３０ are independently: (1) halogen, —SiR ａ (OR ｂ ) (OR ｃ ), and -(C ６ -C １０ C optionally substituted with 1 to 3 substituents independently selected from ６ -C ２０ alkyl, and (2) halogen, -(C １ -C ６ alkyl), and —SiR ａ (OR ｂ ) (OR ｃ C optionally substituted with 1 to 3 substituents independently selected from ６ -C １０ aryl, wherein each R ａ are independently -(C １ -C ６ alkyl), and each R ｂ and each R ｃ are independently -(C １ -C ６ alkyl) and -Si(C １ -C ６ alkyl) ３ is selected from Each X － are independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof; however, R １０ But -(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ alkoxy), -(C １ -C ６ alkoxy), -(C １ -C ６ alkyl) optionally substituted with -(C ６ -C １０ aryl), and C optionally substituted with a substituent selected from carboxy １ -C ６ alkyl, the polyethyleneimine intermediate is 【Chemistry 10】 85. The antimicrobial composition of any one of claims 1 to 84, provided that the antimicrobial composition is selected from:

106. The polyethyleneimine intermediate is 【Chemistry 11】 wherein each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000.

107. 107. The antimicrobial composition of any one of claims 1 to 106, wherein at least 20% of the nitrogen atoms of the polyethyleneimine intermediate are quaternized.

108. the second adduct is of formula (I): 【Chemistry 12】 During the ceremony, Each A independently: 【Chemistry 13】 or a copolymer of any two or more thereof, wherein the attachment of each A forms a carbamate linkage; Each Y ３ are independently H or -O-Y ２ and all Y ３ But it cannot be H, Each Y ２ are independently H or —C(O)—NHR ３０ and all Y ２ is —C(O)—NHR ３０ It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C ２ -C ６ alkylene)-, Each R １０ are independently hydrogen; ＋ (R ２０ ) ３ X － , -(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ alkoxy), -(C １ -C ６ alkoxy), -(C １ -C ６ alkyl) optionally substituted with -(C ６ -C １０ aryl), and C optionally substituted with a substituent selected from carboxy １ -C ６ alkyl, and each R ２０ But independently, C １ -C １８ alkyl; C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N １ -C １８ Heteroalkyl, and -(C １ -C ６ alkyl), -(C １ -C ６ alkoxy), —C(O)O—(C １ -C ６ alkyl), —C(O)NH(C １ -C ６ alkyl), —C(O)N(C １ -C ６ alkyl) ２ , or —OC(O)—(C １ -C ６ C optionally substituted with alkyl ６ -C １０ aryl; Each R ２１ are independently —OH, —(C １ -C ６ alkoxy), carboxy, -(C ６ -C １０ aryl), —C(O)O(C １ -C ６ alkyl), —C(O)—(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ C optionally substituted with a substituent selected from １ -C ６ alkyl, Each R ３０ are independently: (1) halogen, —SiR ａ (OR ｂ ) (OR ｃ ), and -(C ６ -C １０ C optionally substituted with 1 to 3 substituents independently selected from ６ -C ２０ alkyl, (2) halogen, -(C １ -C ６ alkyl), and —SiR ａ (OR ｂ ) (OR ｃ C optionally substituted with 1 to 3 substituents independently selected from ６ -C １０ aryl, and (3) 【Chemistry 14】 wherein each R ａ But independently - (C １ -C ６ alkyl), and each R ｂ and each R ｃ are independently -(C １ -C ６ alkyl) and -Si(C １ -C ６ alkyl) ３ is selected from Each R ４０ are independently -(C １ -C １０ alkylene)- or a 3- to 8-membered cycloalkyl ring; Each X － are independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof; however, R １０ But -(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ alkoxy), -(C １ -C ６ alkoxy), -(C １ -C ６ alkyl) optionally substituted with -(C ６ -C １０ aryl), and C optionally substituted with a substituent selected from carboxy １ -C ６ When alkyl, each A independently represents 【Chemistry 15】 85. The antimicrobial composition of any one of claims 1 to 84, provided that the antimicrobial composition is selected from:

109. the second adduct is of formula (II): 【Chemistry 16】 During the ceremony, Each A independently: 【Chemistry 17】 or a copolymer of any two or more thereof, wherein the attachment of each A forms a carbamate linkage; Each Y ３ are independently H or -O-Y ２ and all Y ３ But it cannot be H, Each Y ２ are independently H or —C(O)—NHR ３０ and all Y ２ is —C(O)—NHR ３０ It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C ２ -C ６ alkylene)-, Each R １０ are independently hydrogen; ＋ (R ２０ ) ３ X － , -(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ alkoxy), -(C １ -C ６ alkoxy), -(C １ -C ６ alkyl) optionally substituted with -(C ６ -C １０ aryl), and C optionally substituted with a substituent selected from carboxy １ -C ６ alkyl, and each R ２０ But independently, C １ -C １８ alkyl; C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N １ -C １８ Heteroalkyl, and -(C １ -C ６ alkyl), -(C １ -C ６ alkoxy), —C(O)O—(C １ -C ６ alkyl), —C(O)NH(C １ -C ６ alkyl), —C(O)N(C １ -C ６ alkyl) ２ , or —OC(O)—(C １ -C ６ C optionally substituted with alkyl ６ -C １０ aryl; Each R ２１ are independently —OH, —(C １ -C ６ alkoxy), carboxy, -(C ６ -C １０ aryl), —C(O)O(C １ -C ６ alkyl), —C(O)—(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ C optionally substituted with a substituent selected from １ -C ６ alkyl, Each R ３０ are independently: (1) halogen, —SiR ａ (OR ｂ ) (OR ｃ ), and -(C ６ -C １０ C optionally substituted with 1 to 3 substituents independently selected from ６ -C ２０ alkyl, (2) halogen, -(C １ -C ６ alkyl), and —SiR ａ (OR ｂ ) (OR ｃ C optionally substituted with 1 to 3 substituents independently selected from ６ -C １０ aryl, and (3) 【Chemistry 18】 wherein each R ａ are independently -(C １ -C ６ alkyl), and each R ｂ and each R ｃ are independently -(C １ -C ６ alkyl) and -Si(C １ -C ６ alkyl) ３ is selected from Each R ４０ are independently -(C １ -C １０ alkylene)- or a 3- to 8-membered cycloalkyl ring; Each X － are independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof; however, R １０ But -(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ alkoxy), -(C １ -C ６ alkoxy), -(C １ -C ６ alkyl) optionally substituted with -(C ６ -C １０ aryl), and C optionally substituted with a substituent selected from carboxy １ -C ６ When alkyl, each A independently represents 【Chemistry 19】 85. The antimicrobial composition of any one of claims 1 to 84, provided that the antimicrobial composition is selected from:

110. A polymer or interpenetrating polymer network comprising the random polymerization / crosslinking product of reagents including (i) a first adduct of a first multifunctional crosslinker and a first quaternary ammonium salt, (ii) a polyol, (iii) a polyethyleneimine intermediate or a second adduct of said polyethyleneimine intermediate and a second multifunctional crosslinker, and (iv) optionally a third multifunctional crosslinker.

111. The first quaternary ammonium salt is 【Chemistry 20】 wherein: R １ But -(C ８ -C ３０ alkyl), -(C ８ -C ３０ heteroalkyl), -(C ８ -C ３０ heteroalkyl)-(C ６ -C １０ aryl), -(C ６ -C １０ aryl), -(C ６ -C １０ aryl)-(C ８ -C ３０ alkyl), -(C ６ -C １０ aryl)-(C ８ -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—, —(C ８ -C ３０ heteroalkyl), -(C ８ -C ３０ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl)-(C ８ -C ３０ heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si; R ２ But -(C １ -C ４ alkyl), -(C １ -C ４ heteroalkyl), -(C １ -C ４ heteroalkyl)-(C ６ -C １０ aryl), -(C ６ -C １０ aryl), -(C ６ -C １０ aryl)-(C １ -C ４ alkyl), -(C ６ -C １０ aryl)-(C １ -C ４ 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, -(C １ -C ４ heteroalkyl), -(C １ -C ４ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl)-(C １ -C ４ heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si; R ３ But -(C １ -C ３０ alkyl), -(C １ -C ３０ heteroalkyl), -(C １ -C ３０ heteroalkyl)-(C ６ -C １０ aryl), -(C ６ -C １０ aryl), -(C ６ -C １０ aryl)-(C １ -C ３０ alkyl), -(C ６ -C １０ aryl)-(C １ -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, -(C １ -C ３０ heteroalkyl), -(C １ -C ３０ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl)-(C １ -C ３０ heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si; A is -(C ３ -C ２０ alkylene)-, -(C ３ -C ２０ heteroalkylene)-, -(C ６ -C １０ arylene)-(C ３ -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 -(C ３ -C ２０ heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; ３ -C ２０ alkylene)- and -(C ３ -C ２０ heteroalkylene)- is -(C ６ -C １０ aryl)-(C １ -C ３ alkyl), -(C ６ -C １０ aryl)-(C １ -C ３ heteroalkyl), -(C １ -C ３ alkyl)-(C ６ -C １０ aryl), -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl); Each R ｍ , R ｎ , R ｐ , and R ｑ independently H and C １ -C ４ alkyl, 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)—; W １１ , W ２１ , W ３１ , and W ４１ are independently 5- to 6-membered cycloalkyl, C ６ -C １０ selected from aryl, 5- to 6-membered heterocycloalkyl, and 5- to 6-membered heteroaryl, wherein said heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and said heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si; x10 is an integer from 1 to 30, y10 is an integer from 0 to 29, and 8≦(x10+y10)≦30; x11 is an integer of 1 to 30, y11 is an integer of 0 to 29, and 8≦(x11+y11)≦30; x20 is an integer of 1 to 4, y20 is an integer of 0 to 3, and x20+y20≦4; x21 is an integer of 1 to 4, y21 is an integer of 0 to 3, and x21+y21≦4; x30 is an integer of 1 to 30, y30 is an integer of 0 to 29, and x30+y30≦30; x31 is an integer of 1 to 30, y31 is an integer of 0 to 29, and x31+y31≦30; x40 is an integer from 1 to 19, y40 is an integer from 1 to 19, and 3≦(x40+y40)≦20; x41 is an integer of 1 to 20, y41 is an integer of 0 to 19, and 3≦(x41+y41)≦20; --OH、-NHR ４ ,-SH,-CO ２ H、-C(O)NHR ４ ,-C(S)NHR ４ 、 【Chemical 21】 is selected from the group consisting of Each R ４ are independently H, -(C ６ -C １０ aryl)-(C １ -C ３ alkyl), -(C ６ -C １０ aryl)-(C １ -C ３ heteroalkyl), -(C １ -C ３ alkyl)-(C ６ -C １０ aryl), -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl), and ６ -C １０ aryl)-(C １ -C ３ heteroalkyl) and -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si; X － is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, borate, or an organically substituted derivative of any of the foregoing.

112. R １ But -(C １２ -C ３０ alkyl), -(C １２ -C ３０ heteroalkyl), -(C １２ -C ３０ alkyl)-(C ６ -C １０ aryl), -(C １２ -C ３０ heteroalkyl)-(C ６ -C １０ aryl), -(C ６ -C １０ aryl)-(C １２ -C ３０ alkyl), and -(C ６ -C １０ aryl)-(C １２ -C ３０ heteroalkyl), １２ -C ３０ heteroalkyl), -(C １２ -C ３０ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl)-(C １２ -C ３０ 112. The polymer or interpenetrating polymer network of claim 111, wherein the (heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si.

113. R ３ But -(C １ -C ４ alkyl), -(C １ -C ４ heteroalkyl), -(C １ -C ４ alkyl)-(C ６ -C １０ aryl), -(C １ -C ４ heteroalkyl)-(C ６ -C １０ aryl), -(C ６ -C １０ aryl)-(C １ -C ４ alkyl), and -(C ６ -C １０ aryl)-(C １ -C ４ heteroalkyl), １ -C ４ heteroalkyl), -(C １ -C ４ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl)-(C １ -C ４ 113. The polymer or interpenetrating polymer network of claim 111 or 112, wherein the heteroalkyl has 1 to 4 heteroatoms independently selected from O, S, and Si.

114. R ２ and R ３ is methyl.

115. A is -(CH ２ ) ｍ - or - (CH ２ CHR ５ -O-) ｎ CH ２ CHR ５ -, wherein m is an integer from 2 to 20, n is 0, 1, 2, 3, 4, or 5, and each R ５ are independently H, -(C ６ -C １０ aryl)-(C １ -C ３ alkyl), -(C ６ -C １０ aryl)-(C １ -C ３ heteroalkyl), -(C １ -C ３ alkyl)-(C ６ -C １０ aryl), -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl), and ６ -C １０ aryl)-(C １ -C ３ heteroalkyl) and -(C １ -C ３ heteroalkyl)-(C ６ -C １０ 115. The polymer or interpenetrating polymer network of any one of claims 111 to 114, wherein (aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si.

116. R ５ is H or methyl.

117. The first quaternary ammonium salt is 【Chemical 22】 or a combination of two or more thereof.

118. 118. The polymer or interpenetrating polymer network of 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 from about 1% to about 50% by weight.

119. 119. The polymer or interpenetrating polymer network of any one of claims 110 to 118, wherein the first multifunctional crosslinker is a first polyisocyanate, the second multifunctional crosslinker, if present, is a second polyisocyanate, and the third multifunctional crosslinker, if present, is a third polyisocyanate, and the first polyisocyanate, second polyisocyanate, and third polyisocyanate are different.

120. 119. The polymer or interpenetrating polymer network of any one of claims 110 to 118, wherein the first multifunctional crosslinker is a first polyisocyanate, the second multifunctional crosslinker, if present, is a second polyisocyanate, and the third multifunctional crosslinker, if present, is a third polyisocyanate, and the first polyisocyanate, second polyisocyanate, and third polyisocyanate are the same.

121. 121. The polymer or interpenetrating polymer network of claim 119 or 120, wherein the first, second, and third polyisocyanates each have an average isocyanate functionality of from 2 to 5.

122. 122. The polymer or interpenetrating polymer network of claim 121, wherein each of the first, second, and third polyisocyanates has an average isocyanate functionality of 3 to 4.

123. 123. The polymer or interpenetrating polymer network of any one of claims 119 to 122, wherein each of the first, second, and third polyisocyanates 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), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

124. 123. The polymer or interpenetrating polymer network of any one of claims 119 to 122, wherein each of the first, second, and third polyisocyanates is independently selected from the group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T-series polyisocyanates, and LUPRANATE® M-series polyisocyanates.

125. 125. The polymer or interpenetrating polymer network of any one of claims 110 to 124, wherein the first multifunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of from about 2% to about 25% by weight.

126. 126. The polymer or interpenetrating polymer network of any one of claims 110-125, wherein the second multifunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1% to about 10% by weight.

127. 127. The polymer or interpenetrating polymer network of any one of claims 110 to 126, wherein the third multifunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1% to about 20% by weight.

128. 128. The polymer or interpenetrating polymer network of any one of claims 110 to 127, wherein the first adduct has an average isocyanate functionality of 2 to 3.

129. 129. The polymer or interpenetrating polymer network of claim 128, wherein the first adduct has an average isocyanate functionality of from about 2.05 to about 2.

3.

130. 130. The polymer or interpenetrating polymer network of any one of claims 110 to 129, wherein 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.

131. 131. The polymer or interpenetrating polymer network of 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. 132. The polymer or interpenetrating polymer network of claims 130 or 131, wherein the polyol has a weight average molecular weight of from about 300 to about 3,000.

133. 133. The polymer or interpenetrating polymer network of any one of claims 130 to 132, wherein the polyol has a weight average molecular weight of from about 400 to about 2000.

134. 124. The polymer or interpenetrating polymer network of any one of claims 130 to 123, wherein the polyol has a weight average molecular weight of from about 600 to about 1500.

135. 135. The polymer or interpenetrating polymer network of 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% to about 40% by weight.

136. the reagent comprises the first multifunctional crosslinker and a second quaternary ammonium salt 【Chemical 23】 wherein: R １ａ , R ２ａ , and R ３ａ are each independently methyl or ethyl; A １ But -(C ３ -C ２０ alkylene)-, -(C ３ -C ２０ heteroalkylene)-, -(C ６ -C １０ arylene)-(C ３ -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 -(C ３ -C ２０ heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; ３ -C ２０ alkylene)- and -(C ３ -C ２０ heteroalkylene)- is -(C ６ -C １０ aryl)-(C １ -C ３ alkyl), -(C ６ -C １０ aryl)-(C １ -C ３ heteroalkyl), -(C １ -C ３ alkyl)-(C ６ -C １０ aryl), -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl); Each R ｍ１ , R ｎ１ , R ｐ１ , and R ｑ１ independently H and C １ -C ４ alkyl, W ４２ is selected from —C(O)—, —C(O)O—, —OC(O)—, —C(O)NH—, and —NHC(O)—; W ４３ is 5- to 6-membered cycloalkyl, C ６ -C １０ selected from aryl, 5- to 6-membered heterocycloalkyl, and 5- to 6-membered heteroaryl, wherein said heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and said heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si; x42 is an integer from 1 to 19, y42 is an integer from 1 to 19, and 3≦(x42+y42)≦20; x43 is an integer of 1 to 20, y43 is an integer of 0 to 19, and 3≦(x43+y43)≦20; Y １ が、-OH、-NHR ４ａ ,-SH,-CO ２ H、-C(O)NHR ４ａ ,-C(S)NHR ４ａ 、 【Chemistry 24】 is selected from the group consisting of Each R ４ａ are independently H, -(C ６ -C １０ aryl)-(C １ -C ３ alkyl), -(C ６ -C １０ aryl)-(C １ -C ３ heteroalkyl), -(C １ -C ３ alkyl)-(C ６ -C １０ aryl), -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl), and ６ -C １０ aryl)-(C １ -C ３ heteroalkyl) and -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si; X － is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, borate, or an organically substituted derivative of any of the foregoing.

137. the reagent comprises a fourth multifunctional crosslinker and a second quaternary ammonium salt 【Chemistry 25】 wherein: R １ａ , R ２ａ , and R ３ａ are each independently methyl or ethyl; A １ But -(C ３ -C ２０ alkylene)-, -(C ３ -C ２０ heteroalkylene)-, -(C ６ -C １０ arylene)-(C ３ -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 -(C ３ -C ２０ heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and Si; ３ -C ２０ alkylene)- and -(C ３ -C ２０ heteroalkylene)- is -(C ６ -C １０ aryl)-(C １ -C ３ alkyl), -(C ６ -C １０ aryl)-(C １ -C ３ heteroalkyl), -(C １ -C ３ alkyl)-(C ６ -C １０ aryl), -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl); Each R ｍ１ , R ｎ１ , R ｐ１ , and R ｑ１ independently H and C １ -C ４ alkyl, W ４２ is selected from —C(O)—, —C(O)O—, —OC(O)—, —C(O)NH—, and —NHC(O)—; W ４３ is 5- to 6-membered cycloalkyl, C ６ -C １０ selected from aryl, 5- to 6-membered heterocycloalkyl, and 5- to 6-membered heteroaryl, wherein said heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and said heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si; x42 is an integer from 1 to 19, y42 is an integer from 1 to 19, and 3≦(x42+y42)≦20; x43 is an integer of 1 to 20, y43 is an integer of 0 to 19, and 3≦(x43+y43)≦20; Y １ が、-OH、-NHR ４ａ ,-SH,-CO ２ H、-C(O)NHR ４ａ ,-C(S)NHR ４ａ 、 ​ is selected from the group consisting of Each R ４ａ are independently H, -(C ６ -C １０ aryl)-(C １ -C ３ alkyl), -(C ６ -C １０ aryl)-(C １ -C ３ heteroalkyl), -(C １ -C ３ alkyl)-(C ６ -C １０ aryl), -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl), and -(C ６ -C １０ aryl), ６ -C １０ aryl)-(C １ -C ３ heteroalkyl) and -(C １ -C ３ heteroalkyl)-(C ６ -C １０ aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si; X － is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, borate, or an organically substituted derivative of any of the foregoing.

138. 138. The polymer or interpenetrating polymer network of claim 137, wherein the fourth multifunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1% to about 15% by weight.

139. 139. The polymer or interpenetrating polymer network of claim 137 or 138, wherein the fourth multifunctional crosslinker is different from the first multifunctional crosslinker, and, if present, the second multifunctional crosslinker, and, if present, the third multifunctional crosslinker.

140. 140. The polymer or interpenetrating polymer network of any one of claims 137 to 139, wherein the fourth multifunctional crosslinker is a fourth polyisocyanate.

141. 141. The polymer or interpenetrating polymer network of 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), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

142. 141. The polymer or interpenetrating polymer network of claim 140, wherein the fourth polyisocyanate is selected from the group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T-series polyisocyanates, and LUPRANATE® M-series polyisocyanates.

143. The second quaternary ammonium salt is 【Chemical 27】 143. The polymer or interpenetrating polymer network of any one of claims 136 to 142, wherein

144. 144. The polymer or interpenetrating polymer network of any one of claims 136-143, wherein the second quaternary ammonium salt is present in the dry polymer or interpenetrating polymer network in an amount from about 1% to about 15% by weight.

145. 145. The polymer or interpenetrating polymer network of any one of claims 136 to 144, wherein the third adduct has an average isocyanate functionality of 2 to 3.

146. 146. The polymer or interpenetrating polymer network of any one of claims 136 to 145, wherein the third adduct has an average isocyanate functionality of from about 2.05 to about 2.

3.

147. 147. The polymer or interpenetrating polymer network of any one of claims 136-146, wherein the third adduct is present in the dry polymer or interpenetrating polymer network in an amount of from about 2% to about 30% by weight.

148. 148. The polymer or interpenetrating polymer network of any one of claims 110-147, wherein the polyethyleneimine intermediate is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.1% to about 50% by weight.

149. 149. The polymer or interpenetrating polymer network of any one of claims 110 to 148, wherein the polyethyleneimine intermediate comprises an optionally substituted hydroxyalkylene functional group that reacts with the first adduct and, if present, the second multifunctional crosslinker.

150. The hydroxyalkylene functional group is —N ＋ (R ２０ ) ３ X － , -(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ alkoxy), -(C １ -C ６ alkoxy), -(C １ -C ６ alkyl) optionally substituted with -(C ６ -C １０ aryl), and C optionally substituted with a substituent selected from carboxy １ -C ６ and each R ２０ But independently, C １ -C １８ alkyl; C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N １ -C １８ Heteroalkyl, and -(C １ -C ６ alkyl), -(C １ -C ６ alkoxy), —C(O)O—(C １ -C ６ alkyl), —C(O)NH(C １ -C ６ alkyl), —C(O)N(C １ -C ６ alkyl) ２ , or —OC(O)—(C １ -C ６ C optionally substituted with alkyl ６ -C １０ aryl, and each X － is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

151. 151. The polymer or interpenetrating polymer network of claim 149 or 150, wherein the hydroxyalkylene functional group is hydroxyethylene, hydroxypropylene, hydroxybutylene, or an oligomer thereof.

152. The polyethyleneimine intermediate comprises the reaction product of a polyethyleneimine, a monoepoxide, and a reagent comprising an alkylating agent, the monoepoxide being -(C ６ -C １０ aryl), and -(C optionally substituted with hydroxy １ -C ６ Alkoxy), C １ -C ６ Alkoxy, C １ -C ６ C optionally substituted with alkyl ６ -C １０ C optionally substituted with a substituent selected from aryl and carboxy １ -C ６ 150. The polymer or interpenetrating polymer network of any one of claims 110 to 149, optionally substituted with alkyl.

153. The monoepoxide is C １ -C ６ 153. The polymer or interpenetrating polymer network of claim 152, which is an alkyl epoxide.

154. Said C １ -C ６ 154. The polymer or interpenetrating polymer network of claim 153, wherein the alkyl epoxide is selected from the group consisting of propyl epoxide, butyl epoxide, and hexyl epoxide.

155. The polyethyleneimine intermediate comprises the reaction product of a polyethyleneimine, a monoepoxide, and optionally a reagent comprising an alkylating agent, wherein the monoepoxide is -(C １ -C ６ alkyl)-N ＋ (R ２０ ) ３ X － and each R ２０ But independently, C １ -C １８ alkyl; C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N １ -C １８ Heteroalkyl, and -(C １ -C ６ alkyl), -(C １ -C ６ alkoxy), —C(O)O—(C １ -C ６ alkyl), —C(O)NH(C １ -C ６ alkyl), —C(O)N(C １ -C ６ alkyl) ２ , or —OC(O)—(C １ -C ６ C optionally substituted with alkyl ６ -C １０ aryl, and each X － is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

156. The alkylating agent may comprise one or more R ２１ -LG, wherein each R ２１ are independently —OH, —(C １ -C ６ alkoxy), carboxy, -(C ６ -C １０ aryl), —C(O)O(C １ -C ６ alkyl), —C(O)—(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ C optionally substituted with a substituent selected from １ -C ６ 156. The polymer or interpenetrating polymer network of any one of claims 152 to 155, wherein each LG is a leaving group selected from alkyl.

157. 157. The polymer or interpenetrating polymer network of claim 156, wherein the alkylating agent is a benzyl halide or a hexyl halide.

158. 150. The polymer or interpenetrating polymer network of any one of claims 110-149, wherein the polyethyleneimine intermediate comprises the reaction product of a reagent comprising polyethyleneimine and a haloalkanol.

159. The haloalkanol is X ３０ -(C ２ -C ６ alkylene)-OH, wherein X ３０ is Cl, Br, or I.

160. 160. The polymer or interpenetrating polymer network of any one of claims 152 to 159, wherein the reagents for the reaction product included in the polyethyleneimine intermediate further comprise a monoisocyanate.

161. The monoisocyanate may comprise one or more R ３０ -NCO, wherein each R ３０ are independently: (1) halogen, —SiR ａ (OR ｂ ) (OR ｃ ), and -(C ６ -C １０ C optionally substituted with 1 to 3 substituents independently selected from ６ -C ２０ alkyl, and (2) halogen, -(C １ -C ６ alkyl), and —SiR ａ (OR ｂ ) (OR ｃ C optionally substituted with 1 to 3 substituents independently selected from ６ -C １０ aryl, wherein each R ａ But independently, C １ -C ６ alkyl, and each R ｂ and each R ｃ are independently -(C １ -C ６ alkyl) and -Si(C １ -C ６ alkyl) ３ 161. The polymer or interpenetrating polymer network of claim 160, selected from:

162. 162. The polymer or interpenetrating polymer network of claim 160 or 161, wherein the monoisocyanate comprises octyl isocyanate, octadecyl isocyanate, or a combination thereof.

163. 163. The polymer or interpenetrating polymer network of any one of claims 152 to 162, wherein the polyethyleneimine has a molecular weight of from about 300 to about 270,000 daltons.

164. 164. The polymer or interpenetrating polymer network of any one of claims 152 to 163, wherein the polyethyleneimine has a molecular weight of from about 10,000 to about 200,000 daltons.

165. 165. The polymer or interpenetrating polymer network of any one of claims 152 to 164, wherein the polyethyleneimine has a molecular weight of from about 25,000 to about 120,000 daltons.

166. 166. The polymer or interpenetrating polymer network of any one of claims 152 to 165, wherein the polyethyleneimine is branched.

167. 166. The polymer or interpenetrating polymer network of any one of claims 152 to 165, wherein the polyethyleneimine is hyperbranched.

168. 168. The polymer or interpenetrating polymer network of any one of claims 152-167, wherein the polyethyleneimine has a ratio of primary to secondary to tertiary amines of from about 1:2:1 to about 1:1:

1.

169. 168. The polymer or interpenetrating polymer network of any one of claims 152 to 167, wherein the polyethyleneimine has a ratio of primary to secondary to tertiary amines of about 1:1:0.

7.

170. The polyethyleneimine intermediate is 【Chemical Formula 28】 or a copolymer of any two or more thereof, wherein: Each Y ３ are independently H or -O-Y ２ and all Y ３ But it cannot be H, Each Y ２ are independently H or —C(O)—NHR ３０ and all Y ２ is —C(O)—NHR ３０ It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C ２ -C ６ alkylene)-, Each R １０ are independently hydrogen; ２０ ) ３ , -(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ alkoxy), -(C １ -C ６ alkoxy), -(C １ -C ６ alkyl) optionally substituted with -(C ６ -C １０ aryl), and C optionally substituted with a substituent selected from carboxy １ -C ６ alkyl, and each R ２０ But independently, C １ -C １８ alkyl; C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N １ -C １８ Heteroalkyl, and -(C １ -C ６ alkyl), -(C １ -C ６ alkoxy), —C(O)O—(C １ -C ６ alkyl), —C(O)NH(C １ -C ６ alkyl), —C(O)N(C １ -C ６ alkyl) ２ , or —OC(O)—(C １ -C ６ C optionally substituted with alkyl ６ -C １０ aryl; Each R ２１ are independently —OH, —(C １ -C ６ alkoxy), carboxy, -(C ６ -C １０ aryl), —C(O)O(C １ -C ６ alkyl), —C(O)—(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ C optionally substituted with a substituent selected from １ -C ６ alkyl, Each R ３０ are independently: (1) halogen, —SiR ａ (OR ｂ ) (OR ｃ ), and -(C ６ -C １０ C optionally substituted with 1 to 3 substituents independently selected from ６ -C ２０ alkyl, and (2) halogen, -(C １ -C ６ alkyl), and —SiR ａ (OR ｂ ) (OR ｃ C optionally substituted with 1 to 3 substituents independently selected from ６ -C １０ aryl, wherein each R ａ are independently -(C １ -C ６ alkyl), and each R ｂ and each R ｃ are independently -(C １ -C ６ alkyl) and -Si(C １ -C ６ alkyl) ３ is selected from Each X － are independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof; however, R １０ But -(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ alkoxy), -(C １ -C ６ alkoxy), -(C １ -C ６ alkyl) optionally substituted with -(C ６ -C １０ aryl), and C optionally substituted with a substituent selected from carboxy １ -C ６ alkyl, the polyethyleneimine intermediate is 【Chemical 29】 150. The polymer or interpenetrating polymer network of any one of claims 110 to 149, wherein the polymer or interpenetrating polymer network is selected from:

171. The polyethyleneimine intermediate is 【Chemistry 30】 wherein each n is an integer independently selected from 1 to 3000, preferably 10 to 1000.

172. the second adduct is of formula (I): 【Chemical 31】 During the ceremony, Each A independently: 【Chemical 32】 or a copolymer of any two or more thereof, wherein the attachment of each A forms a carbamate linkage; Each Y ３ are independently H or -O-Y ２ and all Y ３ But it cannot be H, Each Y ２ are independently H or —C(O)—NHR ３０ and all Y ２ is —C(O)—NHR ３０ It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C ２ -C ６ alkylene)-, Each R １０ are independently hydrogen; ２０ ) ３ , -(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ alkoxy), -(C １ -C ６ alkoxy), -(C １ -C ６ alkyl) optionally substituted with -(C ６ -C １０ aryl), and C optionally substituted with a substituent selected from carboxy １ -C ６ alkyl, and each R ２０ But independently, C １ -C １８ alkyl; C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N １ -C １８ Heteroalkyl, and -(C １ -C ６ alkyl), -(C １ -C ６ alkoxy), —C(O)O—(C １ -C ６ alkyl), —C(O)NH(C １ -C ６ alkyl), —C(O)N(C １ -C ６ alkyl) ２ , or —OC(O)—(C １ -C ６ C optionally substituted with alkyl ６ -C １０ aryl; Each R ２１ are independently —OH, —(C １ -C ６ alkoxy), carboxy, -(C ６ -C １０ aryl), —C(O)O(C １ -C ６ alkyl), —C(O)—(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ C optionally substituted with a substituent selected from １ -C ６ alkyl, Each R ３０ are independently: (1) halogen, —SiR ａ (OR ｂ ) (OR ｃ ), and -(C ６ -C １０ C optionally substituted with 1 to 3 substituents independently selected from ６ -C ２０ alkyl, (2) halogen, -(C １ -C ６ alkyl), and —SiR ａ (OR ｂ ) (OR ｃ C optionally substituted with 1 to 3 substituents independently selected from ６ -C １０ aryl, and (3) 【Chemical 33】 wherein each R ａ are independently -(C １ -C ６ alkyl), and each R ｂ and each R ｃ are independently -(C １ -C ６ alkyl) and -Si(C １ -C ６ alkyl) ３ is selected from Each R ４０ are independently -(C １ -C １０ alkylene)- or a 3- to 8-membered cycloalkyl ring; Each X － are independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof; however, R １０ But -(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ alkoxy), -(C １ -C ６ alkoxy), -(C １ -C ６ alkyl) optionally substituted with -(C ６ -C １０ aryl), and C optionally substituted with a substituent selected from carboxy １ -C ６ When alkyl, each A independently represents 【Chemical 34】 150. The polymer or interpenetrating polymer network of any one of claims 110 to 149, wherein the polymer or interpenetrating polymer network is selected from:

173. the second adduct is of formula (II): 【Chemical 35】 During the ceremony, Each A independently: 【Chemical 36】 or a copolymer of any two or more thereof, wherein the attachment of each A forms a carbamate linkage; Each Y ３ are independently H or -O-Y ２ and all Y ３ But it cannot be H, Each Y ２ are independently H or —C(O)—NHR ３０ and all Y ２ is —C(O)—NHR ３０ It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C ２ -C ６ alkylene)-, Each R １０ are independently hydrogen; ２０ ) ３ , -(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ alkoxy), -(C １ -C ６ alkoxy), -(C １ -C ６ alkyl) optionally substituted with -(C ６ -C １０ aryl), and C optionally substituted with a substituent selected from carboxy １ -C ６ alkyl, and each R ２０ But independently, C １ -C １８ alkyl; C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N １ -C １８ Heteroalkyl, and -(C １ -C ６ alkyl), -(C １ -C ６ alkoxy), —C(O)O—(C １ -C ６ alkyl), —C(O)NH(C １ -C ６ alkyl), —C(O)N(C １ -C ６ alkyl) ２ , or —OC(O)—(C １ -C ６ C optionally substituted with alkyl ６ -C １０ aryl; Each R ２１ are independently —OH, —(C １ -C ６ alkoxy), carboxy, -(C ６ -C １０ aryl), —C(O)O(C １ -C ６ alkyl), —C(O)—(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ C optionally substituted with a substituent selected from １ -C ６ alkyl, Each R ３０ are independently: (1) halogen, —SiR ａ (OR ｂ ) (OR ｃ ), and -(C ６ -C １０ C optionally substituted with 1 to 3 substituents independently selected from ６ -C ２０ alkyl, (2) halogen, -(C １ -C ６ alkyl), and —SiR ａ (OR ｂ ) (OR ｃ C optionally substituted with 1 to 3 substituents independently selected from ６ -C １０ aryl, and (3) 【Chemical 37】 wherein each R ａ are independently -(C １ -C ６ alkyl), and each R ｂ and each R ｃ are independently -(C １ -C ６ alkyl) and -Si(C １ -C ６ alkyl) ３ is selected from Each R ４０ are independently -(C １ -C １０ alkylene)- or a 3- to 8-membered cycloalkyl ring; Each X － are independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof; however, R １０ But -(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ alkoxy), -(C １ -C ６ alkoxy), -(C １ -C ６ alkyl) optionally substituted with -(C ６ -C １０ aryl), and C optionally substituted with a substituent selected from carboxy １ -C ６ When alkyl, each A independently represents 【Chemical 38】 150. The polymer or interpenetrating polymer network of any one of claims 110 to 149, wherein the polymer or interpenetrating polymer network is selected from:

174. 174. The polymer or interpenetrating polymer network of 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 from about 1% to about 30% by weight.

175. 175. The polymer or interpenetrating polymer network of any one of claims 110 to 174, wherein the reagents for the random polymerization / crosslinking product included in the polymer or interpenetrating polymer network further comprise a water soluble polymer.

176. 176. The polymer or interpenetrating polymer network of claim 175, wherein the water-soluble polymer is crosslinked with (a) the first multifunctional crosslinker incorporated in the first adduct, (b) the second multifunctional crosslinker, if present, incorporated in the second adduct, (c) the third multifunctional crosslinker, if present, or (d) any combination of two or more thereof.

177. 177. The polymer or interpenetrating polymer network of claims 175 or 176, wherein the water soluble polymer is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.5% to about 15% by weight.

178. 179. The polymer or interpenetrating polymer network of any one of claims 175-178, 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(hydroxyethyl acrylate-co-alkyl methacrylate), poly(hydroxyethyl acrylate-co-alkyl acrylate), polyacrylamide, polyethyleneimine intermediates, copolymers of two or more thereof, copolymers of one or more thereof with polyvinylpyrrolidone poly(glycidyl acrylate) or poly(glycidyl methacrylate), and combinations or blends of two or more thereof.

179. 179. The polymer or interpenetrating polymer network of any one of claims 175 to 178, wherein the water soluble polymer is hydroxyethyl cellulose or a hydrophobically modified derivative thereof.

180. 179. The polymer or interpenetrating polymer network of any one of claims 175-178, wherein the water soluble polymer is another polyethyleneimine intermediate.

181. The reagent for the random polymerization / crosslinking product contained in the polymer or interpenetrating polymer network is HO—(C ｎ H ２ｎ )-OH and HO-(C ｎ H ２ｎ－２ 181. The polymer or interpenetrating polymer network of any one of claims 110 to 180, further comprising a chain extender selected from the group consisting of: —CH— ...

182. 182. The polymer or interpenetrating polymer network of claim 181, wherein the chain extender is propanediol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexanedimethanol, or a combination of two or more thereof.

183. 183. The polymer or interpenetrating polymer network of claims 181 or 182, wherein the chain extender is present in the dry polymer or interpenetrating polymer network in an amount of from about 0.5% to about 10% by weight.

184. 185. A composition comprising the polymer or interpenetrating polymer network of any one of claims 110 to 184.

185. 【Chemical 39】 or copolymers of any two or more thereof, wherein: Each Y ３ are independently H or -O-Y ２ and all Y ３ But it cannot be H, Each Y ２ are independently H or —C(O)—NHR ３０ and all Y ２ is —C(O)—NHR ３０ It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C ２ -C ６ alkylene)-, Each R １０ But, -N ＋ (R ２０ ) ３ X － C substituted with １ -C ６ alkyl, and each R ２０ But independently, C １ -C １８ alkyl; C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N １ -C １８ Heteroalkyl, and -(C １ -C ６ alkyl), -(C １ -C ６ alkoxy), —C(O)O—(C １ -C ６ alkyl), —C(O)NH(C １ -C ６ alkyl), —C(O)N(C １ -C ６ alkyl) ２ , or —OC(O)—(C １ -C ６ C optionally substituted with alkyl ６ -C １０ aryl; Each R ２１ are independently —OH, —(C １ -C ６ alkoxy), carboxy, -(C ６ -C １０ aryl), —C(O)O(C １ -C ６ alkyl), —C(O)—(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ C optionally substituted with a substituent selected from １ -C ６ alkyl, Each R ３０ are independently: (1) halogen, —SiR ａ (OR ｂ ) (OR ｃ ), and -(C ６ -C １０ C optionally substituted with 1 to 3 substituents independently selected from ６ -C ２０ alkyl, and (2) halogen, -(C １ -C ６ alkyl), and —SiR ａ (OR ｂ ) (OR ｃ C optionally substituted with 1 to 3 substituents independently selected from ６ -C １０ aryl, wherein each R ａ are independently -(C １ -C ６ alkyl), and each R ｂ and each R ｃ are independently -(C １ -C ６ alkyl) and -Si(C １ -C ６ alkyl) ３ is selected from Each X － are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and organically substituted derivatives thereof.

186. Each Y ２ The antibacterial compound of claim 185, wherein is H.

187. The compound is 【Chemistry 40】 187. The antibacterial compound of claim 185 or 186, wherein each n is an integer independently 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 crosslinker, wherein the polyethyleneimine intermediate is 【Chemistry 41】 or a copolymer of any two or more thereof, wherein: Each Y ３ are independently H or -O-Y ２ and all Y ３ But it cannot be H, Each Y ２ are independently H or —C(O)—NHR ３０ and all Y ２ is —C(O)—NHR ３０ It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C ２ -C ６ alkylene)-, Each R １０ But, -N ＋ (R ２０ ) ３ X － C substituted with １ -C ６ alkyl, and each R ２０ But independently, C １ -C １８ alkyl; C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N １ -C １８ Heteroalkyl, and -(C １ -C ６ alkyl), -(C １ -C ６ alkoxy), —C(O)O—(C １ -C ６ alkyl), —C(O)NH(C １ -C ６ alkyl), —C(O)N(C １ -C ６ alkyl) ２ , or —OC(O)—(C １ -C ６ C optionally substituted with alkyl ６ -C １０ aryl; Each R ２１ are independently —OH, —(C １ -C ６ alkoxy), carboxy, -(C ６ -C １０ aryl), —C(O)O(C １ -C ６ alkyl), —C(O)—(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ C optionally substituted with a substituent selected from １ -C ６ alkyl, Each R ３０ are independently: (1) halogen, —SiR ａ (OR ｂ ) (OR ｃ ), and -(C ６ -C １０ C optionally substituted with 1 to 3 substituents independently selected from ６ -C ２０ alkyl, and (2) halogen, -(C １ -C ６ alkyl), and —SiR ａ (OR ｂ ) (OR ｃ C optionally substituted with 1 to 3 substituents independently selected from ６ -C １０ aryl, wherein each R ａ are independently -(C １ -C ６ alkyl), and each R ｂ and each R ｃ are independently -(C １ -C ６ alkyl) and -Si(C １ -C ６ alkyl) ３ is selected from Each X － are independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

189. 189. The random polymerization product of claim 188, wherein the crosslinking agent is a polyisocyanate.

190. 190. The random polymerization product of 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), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

191. 190. The random polymerization product of claim 189, wherein the polyisocyanates are independently selected from the group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T-series polyisocyanates, and LUPRANATE® M-series polyisocyanates.

192. The random polymerization product is of formula (I): 【Chemistry 42】 During the ceremony, Each A independently: 【Chemistry 43】 or a copolymer of any two or more thereof, wherein the attachment of each A forms a carbamate linkage; Each Y ３ are independently H or -O-Y ２ and all Y ３ But it cannot be H, Each Y ２ are independently H or —C(O)—NHR ３０ and all Y ２ is —C(O)—NHR ３０ It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C ２ -C ６ alkylene)-, Each R １０ But, -N ＋ (R ２０ ) ３ X － C substituted with １ -C ６ alkyl, and each R ２０ But independently, C １ -C １８ alkyl; C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N １ -C １８ Heteroalkyl, and -(C １ -C ６ alkyl), -(C １ -C ６ alkoxy), —C(O)O—(C １ -C ６ alkyl), —C(O)NH(C １ -C ６ alkyl), —C(O)N(C １ -C ６ alkyl) ２ , or —OC(O)—(C １ -C ６ C optionally substituted with alkyl ６ -C １０ aryl; Each R ２１ are independently —OH, —(C １ -C ６ alkoxy), carboxy, -(C ６ -C １０ aryl), —C(O)O(C １ -C ６ alkyl), —C(O)—(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ C optionally substituted with a substituent selected from １ -C ６ alkyl, Each R ３０ are independently: (1) halogen, —SiR ａ (OR ｂ ) (OR ｃ ), and -(C ６ -C １０ C optionally substituted with 1 to 3 substituents independently selected from ６ -C ２０ alkyl, (2) halogen, -(C １ -C ６ alkyl), and —SiR ａ (OR ｂ ) (OR ｃ C optionally substituted with 1 to 3 substituents independently selected from ６ -C １０ aryl, and (3) 【Chemical 44】 wherein each R ａ are independently -(C １ -C ６ alkyl), and each R ｂ and each R ｃ are independently -(C １ -C ６ alkyl) and -Si(C １ -C ６ alkyl) ３ is selected from Each R ４０ are independently -(C １ -C １０ alkylene)- or a 3- to 8-membered cycloalkyl ring; Each X － is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

193. The random polymerization product is of formula (II): 【Chemistry 45】 During the ceremony, Each A independently: 【Chemistry 46】 or a copolymer of any two or more thereof, wherein the attachment of each A forms a carbamate linkage; Each Y ３ are independently H or -O-Y ２ and all Y ３ But it cannot be H, Each Y ２ are independently H or —C(O)—NHR ３０ and all Y ２ is —C(O)—NHR ３０ It cannot be, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000; Z is -(C ２ -C ６ alkylene)-, Each R １０ But, -N ＋ (R ２０ ) ３ X － C substituted with １ -C ６ alkyl, and each R ２０ But independently, C １ -C １８ alkyl; C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N １ -C １８ Heteroalkyl, and -(C １ -C ６ alkyl), -(C １ -C ６ alkoxy), —C(O)O—(C １ -C ６ alkyl), —C(O)NH(C １ -C ６ alkyl), —C(O)N(C １ -C ６ alkyl) ２ , or —OC(O)—(C １ -C ６ C optionally substituted with alkyl ６ -C １０ aryl; Each R ２１ are independently —OH, —(C １ -C ６ alkoxy), carboxy, -(C ６ -C １０ aryl), —C(O)O(C １ -C ６ alkyl), —C(O)—(C ６ -C １０ aryl), and -(C optionally substituted with -OH １ -C ６ C optionally substituted with a substituent selected from １ -C ６ alkyl, Each R ３０ are independently: (1) halogen, —SiR ａ (OR ｂ ) (OR ｃ ), and -(C ６ -C １０ C optionally substituted with 1 to 3 substituents independently selected from ６ -C ２０ alkyl, (2) halogen, -(C １ -C ６ alkyl), and —SiR ａ (OR ｂ ) (OR ｃ C optionally substituted with 1 to 3 substituents independently selected from ６ -C １０ aryl, and (3) 【Chemistry 47】 wherein each R ａ are independently -(C １ -C ６ alkyl), and each R ｂ and each R ｃ are independently -(C １ -C ６ alkyl) and -Si(C １ -C ６ alkyl) ３ is selected from Each R ４０ are independently -(C １ -C １０ alkylene)- or a 3- to 8-membered cycloalkyl ring; Each X － is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organically substituted derivatives thereof.

194. 188. A composition comprising the antimicrobial compound of any one of claims 185 to 187.

195. A composition comprising the random polymerization product of any one of claims 188 to 193.

196. 194. An antimicrobial coating, coating fluid, or spray fluid comprising the composition of any one of claims 1-109, 185-187, or 188-193.

197. 202. A device, apparatus, equipment, or accessory comprising the coating, coating fluid, or spray fluid of claim 196.

198. 200. The device, apparatus, equipment, or accessory of claim 197, wherein the coating or spraying fluid is water-soluble or water-dispersible.

199. 199. The device, equipment, apparatus, or accessory of claim 197 or 198, wherein the device, equipment, apparatus, or accessory is selected from the group consisting of a filter, an air purifier, and a mask.

200. 200. The device, equipment, apparatus, or accessory of claim 197 or 198, wherein the device, equipment, apparatus, or accessory is selected from the group consisting of a keyboard, a keypad, a stylus pen, a mouse, a handheld device, a remote control, a touch screen, a telephone, a handheld device, and a display.

201. 200. A personal-care appliance comprising the coating, coating fluid, or spray fluid of claim 196.

202. 202. The personal-care appliance of claim 201, wherein the coating fluid or the spray fluid is water-soluble or water-dispersible.

203. 194. A method of disinfecting a surface, the method comprising applying a composition according to any one of claims 1-109, 185-187, or 188-193.

204. 194. A method of reducing antimicrobial growth on a surface, comprising applying to said surface a composition of any one of claims 1-109, 185-187, or 188-193.

205. 194. A method of preventing antimicrobial growth on a surface, comprising applying to said surface a composition of any one of claims 1-109, 185-187, or 188-193.

206. 206. The method of any one of claims 203 to 205, further comprising forming a coating solution containing the composition.

207. 207. The method of claim 206, further comprising directing the coating solution onto a surface and providing a coating on the surface through the application of the coating solution to the surface.

208. a polymer or interpenetrating polymer network, (a) reacting a first multifunctional crosslinker with a first quaternary ammonium salt to form a first adduct; (b) optionally reacting the polyethyleneimine intermediate with a second multifunctional crosslinker to form a second adduct; (c) optionally reacting the first multifunctional crosslinker or the fourth multifunctional crosslinker with a second quaternary ammonium salt to form a third adduct; (d) combining (i) the first adduct, (ii) the polyethyleneimine intermediate or the second adduct, and (iii) the third adduct, if present, with an optional polyol and optionally a third multifunctional crosslinker to form an oil phase; (e) dissolving a water-soluble polymer in water to form an aqueous phase; (f) combining the oil phase and the water phase to form an oil-in-water emulsion; and (g) applying the emulsion to a surface and allowing the emulsion to dry and cure on the surface to form the polymer or interpenetrating polymer network on the surface.

209. 209. The polymer or interpenetrating polymer network of claim 208, wherein a blocking agent is added to the oil phase after step (d) but before step (f).

210. 210. The polymer or interpenetrating polymer network of claim 208 or 209, wherein step (d) further comprises combining (i) the first adduct, (ii) the polyethyleneimine intermediate or the second adduct, and (iii) the third adduct, if present, with optionally the polyol, and optionally the third multifunctional crosslinker, in an organic solvent or diluent to form the oil phase.

211. 211. The polymer or interpenetrating polymer network of any one of claims 208-210, 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. 212. The polymer or interpenetrating polymer network of any one of claims 208-211, wherein step (e) further comprises adding a surfactant to the aqueous phase.

213. 212. The polymer or interpenetrating polymer network of any one of claims 208-211, wherein step (e) further comprises adding a defoamer or antifoaming agent to the aqueous phase.

214. 212. The polymer or interpenetrating polymer network of any one of claims 208-211, wherein step (e) further comprises adding a surfactant and either a defoamer or antifoaming agent to the aqueous phase.

215. 215. The polymer or interpenetrating polymer network of any one of claims 208-214, wherein step (f) further comprises performing a direct emulsification process, wherein the emulsion is formed by vigorous shear and mixing.

216. 215. The polymer or interpenetrating polymer network of any one of claims 208-214, wherein step (f) further comprises performing a direct emulsification process, wherein the emulsion is formed by sonication.

217. 215. The polymer or interpenetrating polymer network of any one of claims 208-214, wherein step (f) further comprises performing a phase inversion emulsification process wherein a water-in-oil emulsion is first prepared, followed by phase inversion to form said oil-in-water emulsion.

218. 218. The polymer or interpenetrating polymer network of claim 217, wherein the phase inversion is effected by changing the phase ratio, temperature, surfactant, solvent, or any combination of two or more thereof.

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