Antibacterial coating composition

Abstract

Described herein are quaternary ammonium polymers and compositions with broad-spectrum antimicrobial properties 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. Such coatings 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 / 410,714, 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 every year. Since 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, including 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 that reacts with the first multifunctional crosslinker, a polyol, and optionally a second multifunctional crosslinker; and (ii) an aqueous phase comprising a water-soluble polymer.

[0015] In one aspect, an antimicrobial composition is provided, wherein the water-soluble polymer is crosslinked with one or both of a first adduct and a second multifunctional crosslinker.

[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 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 10aryl), -(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-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-C10 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-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 40is 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 is H, -(C6-C 10aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl), -(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; X - is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, borate, or an organically substituted derivative of any of the foregoing.

[0017] In one aspect, 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 30Heteroalkyl) 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 10aryl) 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 10% 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 15% to about 35% by weight based on the dry weight of the oil phase.

[0025] In one embodiment, the first quaternary ammonium salt is present in the oil phase in an amount of about 20% to about 30% 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 25% by weight based on the dry weight of the oil phase.

[0027] 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.

[0028] In one embodiment, the second multifunctional crosslinker 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.

[0029] In one embodiment, the second multifunctional crosslinker 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.

[0030] In one aspect, the first multifunctional crosslinker is a first polyisocyanate and the second multifunctional crosslinker, if present, is a second polyisocyanate, and the first polyisocyanate and second polyisocyanate are different.

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

[0032] In one embodiment, the first and second polyisocyanates each have an average isocyanate functionality of 2-5.

[0033] In one embodiment, the first and second polyisocyanates each have an average isocyanate functionality of 3-4.

[0034] In one aspect, each of the first and second 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).

[0035] In one aspect, each of the first and second 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.

[0036] In one embodiment, the first adduct has an average isocyanate functionality of 2-3.

[0037] In one embodiment, the first adduct has an average isocyanate functionality of from about 2.05 to about 2.3.

[0038] In one embodiment, the reactive isocyanate functional groups on the first adduct are blocked with a blocking agent.

[0039] 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.

[0040] 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.

[0041] In one aspect, the antimicrobial composition further comprises a deblocking agent.

[0042] In one aspect, the deblocking agent is selected from the group consisting of organotins, organobismuths, and tert-amines.

[0043] In one embodiment, the first adduct is present in the oil phase in an amount of about 15% to about 70% by weight based on the dry weight of the oil phase.

[0044] In one embodiment, the oil phase further comprises an organic solvent or diluent.

[0045] In one embodiment, the organic solvent or diluent in the oil phase is water-miscible.

[0046] In one embodiment, the organic solvent or diluent is acetone.

[0047] 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.

[0048] 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.

[0049] In one aspect, 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.

[0050] 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).

[0051] In one embodiment, the polyol has a weight average molecular weight of about 300 to about 3,000.

[0052] In one embodiment, the polyol has a weight average molecular weight of about 400 to about 2,000.

[0053] In one embodiment, the polyol has a weight average molecular weight of about 600 to about 1,500.

[0054] In one embodiment, the polyol is present in the oil phase in an amount of from about 15% to about 60% by weight based on the dry weight of the oil phase.

[0055] In one embodiment, the polyol is present in the oil phase in an amount of about 20% to about 40% by weight based on the dry weight of the oil phase.

[0056] 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, 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.

[0057] In one embodiment, the water-soluble polymer is hydroxyethyl cellulose or a hydrophobically modified derivative thereof.

[0058] In one embodiment, the water-soluble polymer is polyethyleneimine.

[0059] 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.

[0060] 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.

[0061] 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.

[0062] In one embodiment, in the antimicrobial composition, the aqueous phase further comprises a surfactant.

[0063] In one embodiment, the surfactant is a non-ionic surfactant.

[0064] In one embodiment, the nonionic surfactant has an HLB (hydrophile-lipophile balance) value of about 12 to about 15.

[0065] 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.

[0066] In one embodiment, the surfactant is present in the aqueous phase in an amount of from about 0.01% to about 2% by weight based on the dry weight of the oil phase.

[0067] 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.

[0068] In one embodiment, the aqueous phase further comprises a defoamer or anti-foaming agent.

[0069] In one embodiment, the antifoam agent is FOAMSTAR® ST 2410 (a star polymer-based antifoam agent).

[0070] In one embodiment, the random polymer or interpenetrating polymer network is produced from the random polymerization / crosslinking of the first adduct, the polyol, the water-soluble polymer, and, if present, the second multifunctional crosslinker.

[0071] 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-C 20 alkylene)-, -(CR m1 Rn1 ) 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 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; X - is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, borate, or an organically substituted derivative of any of the foregoing.

[0072] In one embodiment, the oil phase comprises a third 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-C20 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 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; X - is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, borate, or an organically substituted derivative of any of the foregoing.

[0073] In one embodiment, the third multifunctional crosslinker is different from the first multifunctional crosslinker and, if present, the second multifunctional crosslinker.

[0074] In one embodiment, the third multifunctional crosslinker is a third polyisocyanate.

[0075] In one embodiment, the third polyisocyanate has an average isocyanate functionality of 2-5.

[0076] In one embodiment, the third 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).

[0077] In one aspect, the third 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.

[0078] In one aspect, the second quaternary ammonium salt is [ka] (C2DMDEG-Br).

[0079] 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.

[0080] 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.

[0081] In one embodiment, the second adduct has an average isocyanate functionality of 2-3.

[0082] In one embodiment, the second adduct has an average isocyanate functionality of from about 2.05 to about 2.3.

[0083] In one embodiment, the second adduct is present in the oil phase in an amount of about 3% to about 40% by weight based on the dry weight of the oil phase.

[0084] In one embodiment, the random polymer or interpenetrating polymer network is produced from the random polymerization / crosslinking of the first adduct, the second adduct, the polyol, the water-soluble polymer, and, if present, the second multifunctional crosslinker.

[0085] 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.

[0086] In one embodiment, the chain extender is propanediol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexanedimethanol, or a combination of two or more thereof.

[0087] 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.

[0088] In one embodiment, the chain extender is present in the oil phase in an amount of from about 1% to about 5% by weight based on the dry weight of the oil phase.

[0089] In one embodiment, the random polymer or interpenetrating polymer network is produced from the random polymerization / crosslinking of the first adduct, the second adduct, the polyol, the chain extender, the water-soluble polymer, and, if present, the second multifunctional crosslinker.

[0090] In one aspect, there is provided a polymer or interpenetrating polymer network comprising the random polymerization / crosslinking product of reagents comprising: (i) a first adduct of a first multifunctional crosslinker and a first quaternary ammonium salt; (ii) a polyol; (iii) a water-soluble polymer; and (iv) optionally a second multifunctional crosslinker, wherein the water-soluble polymer comprises 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 a combination or blend of two or more thereof, or a copolymer of two or more thereof, or a copolymer of one or more of them with polyvinylpyrrolidone, poly(glycidyl acrylate), or poly(glycidyl methacrylate).

[0091] In one embodiment, 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.

[0092] 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-C30 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-C 10 Arylene)-(C3-C 20 alkylene)-, -(CR m R n ) x40 -W 40 -(CRp 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 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 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; X- is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, borate, or an organically substituted derivative of any of the foregoing.

[0093] 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.

[0094] In one embodiment of the polymer or interpenetrating polymer network, 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 10aryl)-(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.

[0095] In one embodiment of the polymer or interpenetrating polymer network, R 2 and R 3 is methyl.

[0096] 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.

[0097] In one embodiment of the polymer or interpenetrating polymer network, R 5 is H or methyl.

[0098] 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.

[0099] 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 10% to about 50% by weight.

[0100] In one aspect of the polymer or interpenetrating polymer network, the first multifunctional crosslinker is a first polyisocyanate and the second multifunctional crosslinker, if present, is a second polyisocyanate, and the first polyisocyanate and the second polyisocyanate are different.

[0101] 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 first polyisocyanate and the second polyisocyanate are the same.

[0102] In one embodiment of the polymer or interpenetrating polymer network, the first and second polyisocyanates each have an average isocyanate functionality of 2-5.

[0103] In one embodiment of the polymer or interpenetrating polymer network, the first and second polyisocyanates each have an average isocyanate functionality of 3 to 4.

[0104] In one embodiment of the polymer or interpenetrating polymer network, each of the first and second 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).

[0105] In one embodiment of the polymer or interpenetrating polymer network, each of the first and second 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.

[0106] 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 about 5% to about 25% by weight.

[0107] 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 about 5% to about 25% by weight.

[0108] In one embodiment of the polymer or interpenetrating polymer network, the first polyisocyanate and the first adduct each have an average isocyanate functionality of 2 to 3.

[0109] In one embodiment of the polymer or interpenetrating polymer network, the first polyisocyanate and the first adduct each have an average isocyanate functionality of from about 2.05 to about 2.3.

[0110] 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.

[0111] 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).

[0112] 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.

[0113] In one embodiment of the polymer or interpenetrating polymer network, the polyol has a weight average molecular weight of about 400 to about 2000.

[0114] 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.

[0115] 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 20% to about 40% by weight.

[0116] 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-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)—; W43 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 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; X - is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, borate, or an organically substituted derivative of any of the foregoing.

[0117] In one embodiment of the polymer or interpenetrating polymer network, the reagent comprises a third 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-C 10 aryl); Each R m1 , R n1 , R p1 , and Rq1 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 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; X -is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, borate, or an organically substituted derivative of any of the foregoing.

[0118] 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 about 5% to about 25% by weight.

[0119] In one embodiment of the polymer or interpenetrating polymer network, the third multifunctional crosslinker is different from the first multifunctional crosslinker and, if present, the second multifunctional crosslinker.

[0120] In one embodiment of the polymer or interpenetrating polymer network, the third multifunctional crosslinker is a third polyisocyanate.

[0121] In one embodiment of the polymer or interpenetrating polymer network, each of the third 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).

[0122] In one embodiment of the polymer or interpenetrating polymer network, the third 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.

[0123] In embodiments of the polymer or interpenetrating polymer network, the second quaternary ammonium salt is [ka] (C2DMDEG-Br).

[0124] 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.

[0125] In one embodiment of the polymer or interpenetrating polymer network, the second adduct has an average isocyanate functionality of 2 to 3.

[0126] In one embodiment of the polymer or interpenetrating polymer network, the second adduct has an average isocyanate functionality of from about 2.05 to about 2.3.

[0127] In one embodiment of the polymer or interpenetrating polymer network, the reagent 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.

[0128] 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.

[0129] 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.

[0130] In one aspect, a composition is provided that includes the above-described polymer or interpenetrating polymer network.

[0131] In one aspect, there is provided an antimicrobial coating, coating fluid, or spray fluid comprising the above-described composition.

[0132] In one aspect, a device, apparatus, equipment, or accessory is provided that includes the coating, coating fluid, or spray fluid.

[0133] In one aspect, there is provided the above device, apparatus, equipment, or accessory, wherein the coating fluid or spray fluid is water-soluble or water-dispersible.

[0134] In one aspect, there is provided the above device, equipment, apparatus, or accessory, wherein the device, equipment, apparatus, or accessory is selected from the group consisting of a filter, an air purifier, and a mask.

[0135] In one aspect, there is provided a device, apparatus, equipment, or accessory as described above, wherein the device, apparatus, equipment, 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.

[0136] In one aspect, a personal-care appliance is provided that includes the coating, coating fluid, or spray fluid described above.

[0137] In one aspect, the coating or spray fluid is water-soluble or water-dispersible.

[0138] In one aspect, a method of disinfecting a surface is provided, comprising applying the composition described above.

[0139] In one aspect, a method of reducing antimicrobial growth on a surface is provided, comprising applying the above-described composition to the surface.

[0140] In one aspect, a method of preventing antimicrobial growth on a surface is provided, comprising applying the above-described composition to the surface.

[0141] In one aspect, the above method further comprises forming a coating solution containing the composition.

[0142] In one aspect, the aforementioned method further comprises directing the coating solution to a surface and providing a coating on the surface through application of the coating solution to the surface.

[0143] In one 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 first multifunctional crosslinker or the third multifunctional crosslinker with a second quaternary ammonium salt to form a second adduct; (c) combining the first adduct, and, if present, the second adduct, with a polyol and, optionally, a second multifunctional crosslinker to form an oil phase; (d) dissolving a water-soluble polymer in water to form an aqueous phase; (e) combining the oil and water phases to form an oil-in-water emulsion; and (f) 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.

[0144] In one aspect, the blocking agent is added to the oil phase after step (c) but before step (e).

[0145] In one aspect, step (c) further comprises combining the first adduct, and, if present, the second adduct, with a polyol, and optionally a second multifunctional crosslinker, in an organic solvent or diluent to form an oil phase.

[0146] In one embodiment, step (d) further comprises adding a chain extender to the oil phase or the water phase.

[0147] In one embodiment, step (d) further comprises adding a surfactant to the aqueous phase.

[0148] In one aspect, step (d) further comprises adding a defoamer or anti-foaming agent to the aqueous phase.

[0149] In one embodiment, step (d) further comprises adding a surfactant and either a defoamer or anti-foaming agent to the aqueous phase.

[0150] In one aspect, step (e) further comprises performing a direct emulsification process, where the emulsion is formed by vigorous shear and mixing.

[0151] In one aspect, step (e) further comprises performing a direct emulsification process, wherein the emulsion is formed by sonication.

[0152] In one aspect, step (e) 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.

[0153] In one aspect, the phase inversion is achieved by changing the phase ratio, temperature, surfactant, solvent, or any combination of two or more thereof.

[0154] 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.

[0155] Other embodiments are also described and listed herein. DETAILED DESCRIPTION OF THE INVENTION

[0156] 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.

[0157] 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.

[0158] 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.

[0159] 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."

[0160] 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.

[0161] 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.

[0162] 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.

[0163] 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.

[0164] 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.

[0165] 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.

[0166] 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.

[0167] 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.

[0168] 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.

[0169] 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.

[0170] 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.

[0171] As used herein, unless otherwise specified, "independently selected" indicates that each of the specified groups is independently selected from the subsequent list of species.

[0172] The terms "statistically significant" or "significantly" refer to statistical significance, generally meaning a difference of two standard deviations (2SD) or greater.

[0173] 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.

[0174] 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.

[0175] 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 of Leverkusen, Germany), which are aliphatic polyisocyanates based on HDI (hexamethylene diisocyanate) trimer; DESMODUR® Z4470SN (made by Covestro Deutschland AG of 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.

[0176] As used herein, the term "antimicrobial" is generally used to indicate that at least some level of pathogens are killed by a composition or coating on a portion of a surface. For example, antimicrobial may be used to indicate biocontrol efficacy, a kill 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, may include any species of bacteria, viruses, fungi, including molds and yeasts, or spores. Thus, antimicrobial herein includes antiviral, antibacterial, and antifungal.

[0177] 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.

[0178] 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.

[0179] 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.

[0180] 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.

[0181] 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 understood that the 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 technology, which is defined solely by the claims. Definitions of common terms in immunology and molecular biology can be found in The Merck Manual of Diagnosis and Therapy, 3 The Encyclopedia of Molecular Cell Biology and Molecular Medicine, 4 Molecular Biology and Biotechnology: a Comprehensive Desk Reference, 5 Immunology, 6 Janeway's Immunobiology, 7 Lewin's Genes XI, 8 Molecular Cloning: A Laboratory Manual. 9 Basic Methods in Molecular Biology, 10 Laboratory Methods in Enzymology, 11 Current Protocols in Molecular Biology (CPMB), 12 Current Protocols in Protein Science (CPPS), 13 and Current Protocols in Immunology (CPI) 14 can be seen in.

[0182] Other terms are defined herein within the description of various aspects of the technology.

[0183] 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.

[0184] 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.

[0185] 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.

[0186] 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 log). 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.

[0187] 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, PA), and SILVERSAN™ from PPG Industrial Coatings (Pittsburgh, PA). However, while these products generally 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 falls 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.

[0188] 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.

[0189] Park et al. (2006) 17 reported antimicrobially active polymers made 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.

[0190] 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.

[0191] 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.

[0192] Some researchers have reported antibacterial polyurethane polymers with quaternary ammonium functional groups. 20、21、22 However, these have a number of 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.

[0193] 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.

[0194] 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.

[0195] 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.

[0196] 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 polyol; (iii) a water-soluble polymer; and (iv) optionally a second multifunctional crosslinker. In some embodiments, 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 a combination or blend of two or more thereof, or a copolymer of two or more thereof, or a copolymer of one or more of them with polyvinylpyrrolidone, poly(glycidyl acrylate), or poly(glycidyl methacrylate).

[0197] In another aspect, a polymer or interpenetrating polymer network is provided that comprises the random polymerization / crosslinking product of reagents that comprise, consist essentially of, or consist of: (i) a first adduct of a first multifunctional crosslinker and a first quaternary ammonium salt; (ii) a polyol; (iii) a water-soluble polymer; and (iv) optionally a second multifunctional crosslinker, wherein the water-soluble polymer is selected from the group consisting of hydroxyethyl cellulose, hydroxypropyl cellulose, methyl cellulose, hydrophobically modified cellulose, polyvinyl alcohol, poly(hydroxyethyl methacrylate-co-alkyl methacrylate), poly(hydroxyethyl methacrylate), Provided herein is a polymer or interpenetrating polymer network that comprises, consists essentially of, or consists of poly(hydroxyethyl acrylate-co-alkyl acrylate), poly(hydroxyethyl acrylate-co-alkyl methacrylate), poly(hydroxyethyl acrylate-co-alkyl acrylate), polyethyleneimine, polyacrylamide, 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).

[0198] 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.

[0199] 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 -(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 -(CRm 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-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 10Arylene)-(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 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 10aryl), -(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; X - is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, borate, or an organically substituted derivative of any of the foregoing.

[0200] In some embodiments, 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. In some embodiments, R 1 is -(C 12 -C 30 In some embodiments, R 1has 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, R 1 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.

[0201] 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 10In 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 R n ) 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.

[0202] 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 10aryl)-(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; 10 In 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.

[0203] 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.

[0204] 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 10 aryl)-(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)-.

[0205] 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.

[0206] 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 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, R 5 is H or methyl.

[0207] 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 10aryl)-(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-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. In some embodiments, Y is [ka] where each R 4is 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.

[0208] X - can be independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, 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.

[0209] In some embodiments, the first quaternary ammonium salt is [ka] Or a combination of two or more of them.

[0210] The first quaternary ammonium salt can be present in the dry polymer or interpenetrating polymer network in an amount of about 10% to about 50% by weight, including about 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 15% to about 40% by weight. In some embodiments, the first quaternary ammonium salt is present in the dry polymer or interpenetrating polymer network in an amount of about 20% to about 35% 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 0.3 mN / g to about 1.0 mN / g, including 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.

[0211] 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.

[0212] 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.

[0213] In some embodiments, the first multifunctional crosslinker is a first polyisocyanate, and the second multifunctional crosslinker, if present, is a second polyisocyanate, and the first polyisocyanate and the second polyisocyanate are different. In some embodiments, the first multifunctional crosslinker is a first polyisocyanate, and the second multifunctional crosslinker, if present, is a second polyisocyanate, and the first polyisocyanate and the second polyisocyanate are the same.

[0214] One or both of the first and second 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-cyclohexylisocyanate) (H12MDI), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

[0215] In some embodiments, one or both of the first and second 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. 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).

[0216] The first multifunctional crosslinker can be present in the dry polymer or interpenetrating polymer network in an amount of about 5% to about 25% by weight, including 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.

[0217] The second multifunctional crosslinker can be present in the dry polymer or interpenetrating polymer network in an amount of about 5% to about 25% by weight, including 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 second multifunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of about 10% to about 20% by weight, or about 5% to about 20% by weight.

[0218] 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.

[0219] 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.

[0220] 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).

[0221] In some embodiments, the polyol comprises, consists essentially of, or consists of a polyether polyol, a polyester polyol, or a combination thereof.

[0222] 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.

[0223] The polyol can be present in the dry polymer or interpenetrating polymer network in an amount of about 15% to about 60% by weight, including 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, or 60% 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 20% to about 40% by weight.

[0224] In some embodiments, the polyol is pre-reacted with a second polyisocyanate to form an isocyanate-endcapped prepolymer.

[0225] The reagent comprises (i) a first multifunctional crosslinker or a third 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-C20 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 is H, (C-(C6-C 10 aryl)-(C1-C3 alkyl), -(C6-C 10 aryl)-(C1-C3 heteroalkyl), -(C1-C3 alkyl)-(C6-C 10 aryl), -(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 aryl), -(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; X - is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, borate, or an organically substituted derivative of any of the foregoing.

[0226] The third multifunctional crosslinker can be present in the dry polymer or interpenetrating polymer network in an amount of about 5% to about 25% by weight, including 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 third 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.

[0227] The third multifunctional crosslinker can be different from the first multifunctional crosslinker and, if present, the second multifunctional crosslinker.

[0228] In some embodiments, the third multifunctional crosslinker is a third polyisocyanate. In some embodiments, the third 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 third 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.

[0229] In some embodiments, the second quaternary ammonium salt is [ka] (C2DMDEG-Br).

[0230] 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.

[0231] In some embodiments, the second adduct has an average isocyanate functionality of 2 to 3. In some embodiments, the second adduct has an average isocyanate functionality of 2.05 to about 2.3.

[0232] The reagent 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.

[0233] 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) a polyol; (iii) a water-soluble polymer; (iv) optionally a second multifunctional crosslinker; (v) optionally, a random polymerization / crosslinking product of reagents comprising, consisting essentially of, or consisting of: (a) the first multifunctional crosslinker or a third multifunctional crosslinker and (b) a second adduct of a second quaternary ammonium salt; and (vi) optionally a chain extender.

[0234] In another aspect, a polymer or interpenetrating polymer network is provided 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 polyol; (iii) a water-soluble polymer; (iv) optionally a second multifunctional crosslinker; (v) optionally, a random polymerization / crosslinking product of reagents comprising, consisting essentially of, or consisting of: (a) the first multifunctional crosslinker or a third multifunctional crosslinker and (b) a second adduct of a second quaternary ammonium salt; and (vi) optionally, a chain extender, wherein the water-soluble polymer is selected from the group consisting of hydroxyethyl cellulose, hydroxypropyl cellulose, methyl cellulose, hydrophobically modified cellulose, polyvinyl alcohol, poly(hydroxyethyl methacrylate), ... Provided herein is a polymer or interpenetrating polymer network that comprises, consists essentially of, or consists of poly(hydroxyethyl methacrylate-co-alkyl acrylate), poly(hydroxyethyl acrylate-co-alkyl methacrylate), poly(hydroxyethyl acrylate-co-alkyl methacrylate), poly(hydroxyethyl acrylate-co-alkyl acrylate), polyethyleneimine, polyacrylamide, 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).

[0235] 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, a chain extender (if present), water, and a water-soluble polymer (if reactive). Similarly, in some embodiments, a second quaternary ammonium salt reacts with the first polyisocyanate or a third polyisocyanate to form a second adduct, which retains unreacted isocyanate functional groups from the first or third polyisocyanate. In some embodiments, about 10% to about 40%, preferably about 25% to 33%, of the isocyanate functional groups on the first polyisocyanate are converted, for example, to urethanes or ureas, by reaction with the second quaternary ammonium salt. If present, the second multifunctional crosslinker and / or second adduct may also react with one or more of the polyol, chain extender (if present), water, and water-soluble polymer (if reactive). The first adduct and second adduct are preformed before interacting with the polyol, chain extender (if present), and water-soluble polymer.

[0236] 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 first multifunctional crosslinker or the third multifunctional crosslinker with a second quaternary ammonium salt to form a second adduct; (c) combining the first adduct, and, if present, the second adduct, with a polyol and, optionally, a second multifunctional crosslinker to form an oil phase; (d) dissolving a water-soluble polymer in water to form an aqueous phase; (e) combining the oil and water phases to form an oil-in-water emulsion; and (f) 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.

[0237] In some embodiments, the blocking agent is added to the oil phase after step (c) but before step (e).

[0238] In some embodiments, step (c) further comprises combining the first adduct, and, if present, the second adduct, with a polyol, and optionally a second multifunctional crosslinker, in an organic solvent or diluent to form an oil phase.

[0239] In some embodiments, step (d) further comprises adding a chain extender to the oil phase or the water phase.

[0240] In some embodiments, step (d) further comprises adding a surfactant to the aqueous phase. In some embodiments, step (d) further comprises adding a defoamer or anti-foaming agent to the aqueous phase. In some embodiments, step (d) further comprises adding either a surfactant and a defoamer or anti-foaming agent to the aqueous phase.

[0241] In some embodiments, step (e) further comprises performing a direct emulsification process, in which the emulsion is formed by vigorous shear and mixing. In some embodiments, step (e) further comprises performing a direct emulsification process, in which the emulsion is formed by sonication.

[0242] In some embodiments, step (e) 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.

[0243] 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 (e).

[0244] In some embodiments, combining the oil phase and the aqueous phase in step (e) forms a combination of an oil-in-water emulsion and a multiple water-in-oil-in-water emulsion.

[0245] In another aspect, the reagents for preparing the polymers or interpenetrating polymer networks described herein are included in an antimicrobial composition.

[0246] 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; Polyols, and an oil phase optionally comprising a second 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.

[0247] The water-soluble polymer can be a reactive water-soluble polymer that crosslinks with one or both of the first adduct and the second multifunctional crosslinker, hi some embodiments, the water-soluble polymer is a reactive water-soluble polymer that crosslinks with the first adduct, the second multifunctional crosslinker (if present), or the second adduct (if present), or any combination of two or more thereof.

[0248] 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 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.

[0249] The first quaternary ammonium salt incorporated in the first adduct may be present in the oil phase in an amount of about 10% 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 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 about 15% to about 35% by weight, or about 20% to about 30% by weight, based on the dry weight of the oil phase.

[0250] The first multifunctional crosslinker (e.g., first polyisocyanate) incorporated into the first adduct can 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, including 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 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.

[0251] The second multifunctional crosslinker (e.g., second polyisocyanate) can 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, 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%, or 30%, 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 5% to about 20% by weight, based on the dry weight of the oil phase.

[0252] In some embodiments, the reactive isocyanate functional groups on the first adduct and / or the second 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.

[0253] 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.

[0254] 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).

[0255] The first adduct may be present in the oil phase in an amount of about 15% to about 70% by weight based on the dry weight of the oil phase. This includes 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, 40%, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, 50%, 51%, 52%, 53%, 54%, 55%, 56%, 57%, 58%, 59%, 60%, 61%, 62%, 63%, 64%, 65%, 66%, 67%, 68%, 69%, or 70%, or any value therebetween. In some embodiments, the first adduct is present in an amount of 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.

[0256] In some embodiments, the oil phase further comprises a second additive described herein. The second additive may be present in the oil phase in an amount of about 3% to about 40% by weight based on the dry weight of the oil phase, including about 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.

[0257] In some embodiments, the second quaternary ammonium salt incorporated in the second 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 incorporated in the second 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.

[0258] The third multifunctional crosslinker (e.g., a third polyisocyanate) incorporated into the second adduct can 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, including 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) incorporated into the second 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.

[0259] In some embodiments, the oil phase comprises 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 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.

[0260] 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.

[0261] The polyol may be present in the oil phase in an amount of about 15% to about 60% by weight based on the dry weight of the oil phase, including about 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%, or 60%, or any value therebetween. In some embodiments, the polyol is present in the oil phase in an amount of about 20% to about 40% by weight based on the dry weight of the oil phase.

[0262] 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 polymer 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 polymer is 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.

[0263] 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.

[0264] 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.

[0265] 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.

[0266] 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).

[0267] 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 first quaternary ammonium salt, polyol, optional chain extender, water-soluble polymer, first multifunctional crosslinker (e.g., first polyisocyanate), optional second quaternary ammonium salt, the structure and amount of optional second multifunctional crosslinker, and the degree of crosslinking. It will also be appreciated that multifunctional crosslinker(s) other than polyisocyanates can be used, such as, but not limited to, multifunctional epoxides, imines, carbodiimides, and aldehydes.

[0268] 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.

[0269] 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.

[0270] 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.

[0271] 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.

[0272] 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.

[0273] 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.

[0274] 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.

[0275] 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.

[0276] 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.

[0277] 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]

[0278] 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.

[0279] Example 1: A representative example of the present technology [ka] A. Preparation of Adduct-1 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 reacted for 15 hours. After removing the toluene under reduced pressure, a clear viscous liquid (Adduct-1) was obtained.

[0280] B. Preparation of Adduct-1-PTMG Prepolymer 0.54 g (0.54 mmol, 1.08 mmol OH) of polytetramethylene glycol (PTMG, MW=1000) was mixed with 1.83 g of adduct-1 (approximately 5.59 mmol NCO), reacted at 80° C. under nitrogen for 2 hours, and then cooled to room temperature to obtain the adduct-1-PTMG prepolymer.

[0281] C. Preparation of the adduct - l-PTMG-AO 0.07 g (0.96 mmol) of dry acetone oxime (AO) in 0.46 g of dry acetone was added to the adduct-1-PTMG pre-polymer from Example 2. This was mixed thoroughly on a vortex mixer at room temperature for 30 minutes to ensure the mixture was completely homogeneous, followed by gentle mixing for an additional 30 minutes until the oxime was completely reacted, as evidenced by a decrease in the NCO peak monitored by FTIR spectroscopy, to yield the adduct-1-PTMG-AO product.

[0282] D. Preparation of the Aqueous Phase 3.48 g of hydroxyethyl cellulose (HEC, MW=380K, 3.52% aqueous solution) was diluted with 0.63 g of water and the pH was adjusted to 4.0 with 1 N HCl.

[0283] E. Preparation of Oil / Water Emulsion Coating Formulations and Surface Coatings The solution from Step C and the aqueous solution from Step D were mixed thoroughly together in an ultrasonic device, and the resulting emulsion was immediately coated onto PET at a target dry thickness of approximately 25 μm. The coating was allowed to dry at room temperature for 10 minutes, heated to 60°C for approximately 1-2 hours, and then further dried at room temperature overnight. This formulation was found to yield an emulsion "green time" (the time before the emulsion becomes too thick to be coated) of approximately 15 minutes, compared to the control (omitting the oxime isocyanate blocking step), which had a green time of approximately 9 minutes.

[0284] Example 2 Evaluation of the antiviral activity of polymers and / or their coatings This study was conducted to evaluate the antiviral activity of the polymer coating of this technology. All samples and accessories in the evaluation were first disinfected by either high-temperature autoclaving, alcohol cleaning, or irradiation in a UV laminar flow chamber.

[0285] 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.

[0286] 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.

[0287] (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."

[0288] 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.

[0289] 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.

[0290] (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.

[0291] 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.

[0292] 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.

[0293] 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 6A 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.

[0294] 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.

[0295] 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]

[0296] 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.

[0297] 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.

[0298] 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.

[0299] 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.

[0300] 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. 4The 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.

[0301] 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.

[0302] Experimental results - Antiviral activity and toxicity The coating from Example 1 was tested against a variety of bacteria, viruses, and fungi. Selected data is shown in Tables 2 and 3 below. [Table 3] [Table 4]

[0303] In contrast to the coatings of this technology, the quaternary PEI polymer shown below did not form a colorless, transparent, durable water- and alcohol-resistant coating and had only moderate antiviral activity. Two latex quaternary polymers shown below exhibited antiviral activity but were toxic to HuH7 cells. [ka]

[0304] Mundex-W and Mundex-LK (from Munditech, Germany) are two "self-disinfecting polymer emulsions" for treating surfaces. Both were found to have very weak antiviral activity against adenovirus. Not unexpectedly, the water-based Mundex-W did not provide a durable, water- or alcohol-resistant surface coating. The solvent-based Mundex-LK provided a more hydrophobic coating, but its water or alcohol resistance was only marginal. Furthermore, both were found to be toxic to HuH7 cells.

[0305] The LIVINGUARD® face mask contains an antiviral component. The mask exhibited modest antiviral efficiencies of approximately 44% after 1 minute of contact time and approximately 72% after 20 minutes of contact time. These efficiencies were significantly reduced after the mask was preconditioned at 40°C and 85% RH for 96 hours.

[0306] In conclusion, the antimicrobial polymers of the present technology produce surface coatings that exhibit the following properties: (i) high antimicrobial activity against viruses, bacteria, and fungi, (ii) fast acting, (iii) long-lasting, (iv) non-toxic and non-allergenic, (v) no materials leaching from the coating, (vi) colorless and transparent as a surface coating, (vii) easy application to a wide range of surfaces and materials, (viii) durable surface coatings that are resistant to water and common solvents, and (ix) easy and cost-effective to produce. Thus, these antimicrobial polymers represent an improved class of antimicrobial polymers. References: 1 Ellingson, KD, et al. (2020). “Urban Hospital Study-Antimicrobial Surface Coating.” 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).19th Edition,published by Merck Sharp & Dohme Corp.,(ISBN 978-0-911910-19-3). 4 THE ENCYCLOPEDIA OF MOLECULAR CELL BIOLOGY AND MOLECULAR MEDICINE,Robert S.Porter et al.(eds.),published by Blackwell Science Ltd.,1999-2012(ISBN 9783527600908). 5 MOLECULAR BIOLOGY AND BIOTECHNOLOGY:A COMPREHENSIVE DESK REFERENCE,(1995).Robert A.Meyers(ed.),published by VCH Publishers,Inc.(ISBN 1-56081-569-8). 6 IMMUNOLOGY,(2006).Werner Luttmann, published by Elsevier. 7 JANEWAY’S IMMUNOBIOLOGY,(2014).Kenneth Murphy, Allan Mowat, Casey Weaver (eds.), 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). 10 Davis 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. 16 Geczi, Z.,et al.,(2018).“Antimicrobial Silver-Polyethyleneimine Polylactic Acid Polymer Composite Film for Coating Methacrylate-Based Denture Surfaces.”J.of Nanomaterials,2018(6): 1 9. 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 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. 21 Chung, S., et al., (2016). “Antimicrobial Nanostructural Polyurethane Scaffolds.” Ch.17 in ADVANCES IN POLYURETHANE BIOMATERIALS, Cooper SLand 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.

[0307] 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 invention 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(s) and do not constitute any admission as to the accuracy of the dates or contents of these documents.

[0308] 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; Polyols, and an oil phase optionally comprising a second multifunctional crosslinker; (ii) an aqueous phase comprising a water-soluble polymer.

2. 10. The antimicrobial composition of claim 1, wherein the water-soluble polymer is crosslinked with one or both of the first adduct and the second multifunctional crosslinker.

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 But 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 an acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, 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), 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 10% to about 50% by weight, 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 15% to about 35% by weight, based on the dry weight of the oil phase.

12. 12. The antimicrobial composition of any one of claims 1 to 11, wherein the first quaternary ammonium salt is present in the oil phase in an amount of about 20% to about 30% by weight, based on the dry weight of the oil phase.

13. 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 5% to about 25% by weight based on the dry weight of the oil phase.

14. 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.

15. 15. The antimicrobial composition of any one of claims 1 to 14, wherein the second multifunctional crosslinker 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.

16. 16. The antimicrobial composition of any one of claims 1 to 15, wherein the second multifunctional crosslinker 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.

17. 17. The antimicrobial composition of any one of claims 1 to 16, wherein the first multifunctional crosslinker is a first polyisocyanate and the second multifunctional crosslinker, if present, is a second polyisocyanate, and the first polyisocyanate and the second polyisocyanate are different.

18. 17. The antimicrobial composition of any one of claims 1 to 16, wherein the first multifunctional crosslinker is a first polyisocyanate and the second multifunctional crosslinker, if present, is a second polyisocyanate, and the first polyisocyanate and the second polyisocyanate are the same.

19. 19. The antimicrobial composition of claim 17 or 18, wherein the first and second polyisocyanates each have an average isocyanate functionality of 2 to 5.

20. 20. The antimicrobial composition of claim 19, wherein each of the first and second polyisocyanates has an average isocyanate functionality of 3 to 4.

21. 21. The antimicrobial composition of any one of claims 17-20, wherein each of the first and second 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).

22. 21. The antimicrobial composition of any one of claims 17-20, wherein each of the first and second 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.

23. 23. The antimicrobial composition of any one of claims 17 to 22, wherein the first adduct has an average isocyanate functionality of 2 to 3.

24. 24. The antimicrobial composition of claim 23, wherein the first adduct has an average isocyanate functionality of from about 2.05 to about 2.

3.

25. 25. The antimicrobial composition of any one of claims 17 to 24, wherein reactive isocyanate functional groups on the first adduct are blocked with a blocking agent.

26. 26. The antimicrobial composition of claim 25, 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.

27. 27. The antimicrobial composition of claim 26, 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.

28. The antimicrobial composition of any one of claims 25 to 27, further comprising a deblocking agent.

29. 29. The antimicrobial composition of claim 28, wherein the deblocking agent is selected from the group consisting of organotins, organobismuths, and tertiary amines.

30. 30. The antimicrobial composition of any one of claims 1 to 29, wherein the first adduct is present in the oil phase in an amount of from about 15% to about 70% by weight based on the dry weight of the oil phase.

31. 31. The antimicrobial composition of any one of claims 1 to 30, wherein the oil phase further comprises an organic solvent or a diluent.

32. 32. The antimicrobial composition of claim 31, wherein the organic solvent or diluent in the oil phase is water-miscible.

33. 33. The antimicrobial composition of claim 31 or 32, wherein the organic solvent or diluent is acetone.

34. 34. The antimicrobial composition of any one of claims 31 to 33, 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.

35. 35. The antimicrobial composition of any one of claims 31 to 34, 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.

36. 36. The antimicrobial composition of any one of claims 1 to 35, 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.

37. 37. The antimicrobial composition of claim 36, 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).

38. 38. The antimicrobial composition of claim 36 or 37, wherein the polyol has a weight average molecular weight of about 300 to about 3,000.

39. 39. The antimicrobial composition of any one of claims 36 to 38, wherein the polyol has a weight average molecular weight of about 400 to about 2000.

40. 40. The antimicrobial composition of any one of claims 36 to 39, wherein the polyol has a weight average molecular weight of about 600 to about 1500.

41. 41. The antimicrobial composition of any one of claims 1 to 40, wherein the polyol is present in the oil phase in an amount of from about 15% to about 60% by weight based on the dry weight of the oil phase.

42. 42. The antimicrobial composition of any one of claims 1 to 41, wherein the polyol is present in the oil phase in an amount of about 20% to about 40% by weight based on the dry weight of the oil phase.

43. 43. The antimicrobial composition of any one of claims 1 to 42, 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, 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.

44. 43. The antimicrobial composition of any one of claims 1 to 42, wherein the water-soluble polymer is hydroxyethyl cellulose or a hydrophobically modified derivative thereof.

45. 43. The antimicrobial composition of any one of claims 1 to 42, wherein the water-soluble polymer is polyethyleneimine.

46. 46. ​​The antimicrobial composition of any one of claims 1 to 45, 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.

47. 47. The antimicrobial composition of any one of claims 1 to 46, 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.

48. 48. The antimicrobial composition of any one of claims 1 to 47, 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.

49. 49. The antimicrobial composition of any one of claims 1 to 48, wherein the aqueous phase further comprises a surfactant.

50. 50. The antimicrobial composition of claim 49, wherein the surfactant is a non-ionic surfactant.

51. 51. The antimicrobial composition of claim 50, wherein the nonionic surfactant has an HLB (hydrophile-lipophile balance) value of about 12 to about 15.

52. 52. The antimicrobial composition of claim 50 or 51, 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.

53. 53. The antimicrobial composition of any one of claims 49 to 52, wherein the surfactant is present in the aqueous phase in an amount of from about 0.01% to about 2% by weight based on the dry weight of the oil phase.

54. 54. The antimicrobial composition of any one of claims 49 to 53, wherein the surfactant is present in the aqueous phase in an amount of about 0.1 wt % to about 1 wt %, based on the dry weight of the oil phase.

55. 55. The antimicrobial composition of any one of claims 1 to 54, wherein the aqueous phase further comprises an antifoaming or anti-foaming agent.

56. 56. The antimicrobial composition of claim 55, wherein the antifoam agent is FOAMSTAR® ST 2410 (a star polymer-based antifoam agent).

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

58. 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 But 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, borate, or an organically substituted derivative of any of the foregoing.

59. the oil phase comprises a third 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 But 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, borate, or an organically substituted derivative of any of the foregoing.

60. 60. The antimicrobial composition of claim 59, wherein the third multifunctional crosslinker is different from the first multifunctional crosslinker and, if present, the second multifunctional crosslinker.

61. 61. The antimicrobial composition of claim 60, wherein the third multifunctional crosslinker is a third polyisocyanate.

62. 62. The antimicrobial composition of claim 61, wherein the third polyisocyanate has an average isocyanate functionality of 2 to 5.

63. 63. The antimicrobial composition of claim 61 or 62, wherein the third 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).

64. 63. The antimicrobial composition of claim 61 or 62, wherein the third 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.

65. The second quaternary ammonium salt is 【Chemistry 8】 The antibacterial composition of any one of claims 58 to 64, wherein the antibacterial composition is (C2DMDEG-Br).

66. 66. The antimicrobial composition of any one of claims 58-65, 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.

67. 67. The antimicrobial composition of any one of claims 58-66, 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.

68. 68. The antimicrobial composition of any one of claims 58 to 67, wherein the second adduct has an average isocyanate functionality of 2 to 3.

69. 69. The antimicrobial composition of any one of claims 58 to 68, wherein the second adduct has an average isocyanate functionality of from about 2.05 to about 2.

3.

70. 70. The antimicrobial composition of any one of claims 58 to 69, wherein the second adduct is present in the oil phase in an amount of from about 3% to about 40% by weight based on the dry weight of the oil phase.

71. 71. The antimicrobial composition of any one of claims 58-70, wherein a random polymer or interpenetrating polymer network is produced from random polymerization / crosslinking of the first adduct, the second adduct, the polyol, the water-soluble polymer, and, if present, the second multifunctional crosslinker.

72. The oil phase is HO—(C ｎ H ２ｎ )-OH and HO-(C ｎ H ２ｎ－２ 72. The antimicrobial composition of any one of claims 1-56 or 58-71, further comprising a chain extender selected from the group consisting of: —NH——NH——, — ...

73. 73. The antimicrobial composition of claim 72, wherein the chain extender is propanediol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexanedimethanol, or a combination of two or more thereof.

74. 74. The antimicrobial composition of claim 72 or 73, 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.

75. 75. The antimicrobial composition of any one of claims 72 to 74, wherein the chain extender is present in the oil phase in an amount of from about 1% to about 5% by weight based on the dry weight of the oil phase.

76. 76. The antimicrobial composition of any one of claims 72-75, wherein a random polymer or interpenetrating polymer network is produced from random polymerization / crosslinking of the first adduct, the second adduct, the polyol, the chain extender, the water-soluble polymer, and, if present, the second multifunctional crosslinker.

77. 1. A polymer or interpenetrating polymer network comprising the random polymerization / crosslinking product of reagents comprising: (i) a first adduct of a first multifunctional crosslinker and a first quaternary ammonium salt; (ii) a polyol; (iii) a water-soluble polymer; and (iv) optionally a second multifunctional crosslinker, wherein the water-soluble polymer comprises 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 a combination or blend of two or more thereof, or a copolymer of two or more thereof, or a copolymer of one or more of these with polyvinylpyrrolidone, poly(glycidyl acrylate), or poly(glycidyl methacrylate).

78. 78. The polymer or interpenetrating polymer network of claim 77, 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.

79. The first quaternary ammonium salt is 【Chemistry 9】 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 、 【Chemistry 10】 is selected from the group consisting of Each R ４ But 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, borate, or an organically substituted derivative of any of the foregoing.

80. 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 80. The polymer or interpenetrating polymer network of claim 79, wherein the heteroalkyl has 1 to 4 heteroatoms independently selected from O, S, and Si.

81. 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 81. The polymer or interpenetrating polymer network of claim 79 or 80, wherein the (heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si.

82. R ２ and R ３ is methyl.

83. 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), ６ -C １０ aryl)-(C １ -C ３ heteroalkyl) and -(C １ -C ３ heteroalkyl)-(C ６ -C １０ 83. The polymer or interpenetrating polymer network of any one of claims 79 to 82, wherein the (aryl) has 1 to 4 heteroatoms independently selected from O, S, and Si.

84. R ５ is H or methyl.

85. The first quaternary ammonium salt is 【Chemistry 11】 or a combination of two or more thereof.

86. 86. The polymer or interpenetrating polymer network of any one of claims 77 to 85, wherein the first quaternary ammonium salt is present in the dry polymer or interpenetrating polymer network in an amount of from about 10% to about 50% by weight.

87. 87. The polymer or interpenetrating polymer network of any one of claims 77 to 86, wherein the first multifunctional crosslinker is a first polyisocyanate and the second multifunctional crosslinker, if present, is a second polyisocyanate, and the first polyisocyanate and the second polyisocyanate are different.

88. 87. The polymer or interpenetrating polymer network of any one of claims 77 to 86, wherein the first multifunctional crosslinker is a first polyisocyanate and the second multifunctional crosslinker, if present, is a second polyisocyanate, and the first polyisocyanate and the second polyisocyanate are the same.

89. 89. The polymer or interpenetrating polymer network of claim 87 or 88, wherein the first and second polyisocyanates each have an average isocyanate functionality of from 2 to 5.

90. 90. The polymer or interpenetrating polymer network of claim 89, wherein each of the first and second polyisocyanates has an average isocyanate functionality of 3 to 4.

91. 91. The polymer or interpenetrating polymer network of any one of claims 87-90, wherein each of the first and second 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).

92. 91. The polymer or interpenetrating polymer network of any one of claims 87-90, wherein each of the first and second 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.

93. 93. The polymer or interpenetrating polymer network of any one of claims 77 to 92, wherein the first multifunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of from about 5% to about 25% by weight.

94. 93. The polymer or interpenetrating polymer network of any one of claims 77 to 92, wherein the second multifunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of from about 5% to about 25% by weight.

95. 95. The polymer or interpenetrating polymer network of any one of claims 77 to 94, wherein the first polyisocyanate and the first adduct each have an average isocyanate functionality of 2 to 3.

96. 96. The polymer or interpenetrating polymer network of claim 95, wherein the first polyisocyanate and the first adduct each have an average isocyanate functionality of from about 2.05 to about 2.

3.

97. 97. The polymer or interpenetrating polymer network of any one of claims 77 to 96, 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.

98. 97. The polymer or interpenetrating polymer network of any one of claims 77 to 96, 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).

99. 99. The polymer or interpenetrating polymer network of claim 97 or 98, wherein the polyol has a weight average molecular weight of from about 300 to about 3000.

100. 100. The polymer or interpenetrating polymer network of any one of claims 77 to 99, wherein the polyol has a weight average molecular weight of from about 400 to about 2000.

101. 101. The polymer or interpenetrating polymer network of any one of claims 77 to 100, wherein the polyol has a weight average molecular weight of from about 600 to about 1500.

102. 102. The polymer or interpenetrating polymer network of any one of claims 77 to 101, wherein the polyol is present in the dry polymer or interpenetrating polymer network in an amount of from about 20% to about 40% by weight.

103. the reagent comprises the first multifunctional crosslinker and a second quaternary ammonium salt 【Chemistry 12】 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 13】 is selected from the group consisting of Each R ４ａ But 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, borate, or an organically substituted derivative of any of the foregoing.

104. the reagent comprises a third multifunctional crosslinker and a second quaternary ammonium salt 【Chemistry 14】 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 15】 is selected from the group consisting of Each R ４ａ But 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, borate, or an organically substituted derivative of any of the foregoing.

105. 105. The polymer or interpenetrating polymer network of claim 104, wherein the third multifunctional crosslinker is present in the dry polymer or interpenetrating polymer network in an amount of from about 5% to about 25% by weight.

106. 106. The polymer or interpenetrating polymer network of claim 104 or 105, wherein the third multifunctional crosslinker is different from the first multifunctional crosslinker and, if present, the second multifunctional crosslinker.

107. 107. The polymer or interpenetrating polymer network of any one of claims 104 to 106, wherein the third multifunctional crosslinker is a third polyisocyanate.

108. 108. The polymer or interpenetrating polymer network of claim 107, wherein the third 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).

109. 108. The polymer or interpenetrating polymer network of claim 107, wherein the third 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.

110. The second quaternary ammonium salt is 【Chemistry 16】 110. The polymer or interpenetrating polymer network of any one of claims 103 to 109, wherein the polymer or interpenetrating polymer network is (C2DMDEG-Br).

111. 111. The polymer or interpenetrating polymer network of any one of claims 103 to 110, wherein 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.

112. 112. The polymer or interpenetrating polymer network of any one of claims 103 to 111, wherein the second adduct has an average isocyanate functionality of 2 to 3.

113. 113. The polymer or interpenetrating polymer network of any one of claims 103 to 112, wherein the second adduct has an average isocyanate functionality of from about 2.05 to about 2.

3.

114. The reagent is HO—(C ｎ H ２ｎ )-OH and HO-(C ｎ H ２ｎ－２ 114. The polymer or interpenetrating polymer network of any one of claims 77 to 113, further comprising a chain extender selected from the group consisting of: —CH— ...

115. 115. The polymer or interpenetrating polymer network of claim 114, wherein the chain extender is propanediol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexanedimethanol, or a combination of two or more thereof.

116. 116. The polymer or interpenetrating polymer network of claims 114 or 115, 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.

117. 117. A composition comprising the polymer or interpenetrating polymer network of any one of claims 77 to 116.

118. 77. An antimicrobial coating, coating fluid, or spray fluid comprising the composition of any one of claims 1 to 76.

119. 119. A device, apparatus, equipment, or accessory comprising the coating, coating fluid, or spray fluid of claim 118.

120. 120. The device, apparatus, equipment, or accessory of claim 119, wherein the coating or spraying fluid is water-soluble or water-dispersible.

121. 121. The device, equipment, apparatus, or accessory of claim 119 or 120, wherein the device, equipment, apparatus, or accessory is selected from the group consisting of a filter, an air purifier, and a mask.

122. 121. The device, equipment, apparatus, or accessory of claim 119 or 120, 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.

123. 119. A personal-care appliance comprising the coating, coating fluid, or spray fluid of claim 118.

124. 124. The personal-care appliance of claim 123, wherein the coating fluid or the spray fluid is water-soluble or water-dispersible.

125. 77. A method of disinfecting a surface, the method comprising applying a composition according to any one of claims 1 to 76.

126. 77. A method of reducing antimicrobial growth on a surface, comprising applying to said surface a composition according to any one of claims 1 to 76.

127. 77. A method of preventing antimicrobial growth on a surface, comprising applying to said surface a composition according to any one of claims 1 to 76.

128. 128. The method of any one of claims 125 to 127, further comprising forming a coating solution containing the composition.

129. 129. The method of claim 128, further comprising directing the coating solution to a surface and providing a coating on the surface through the application of the coating solution to the surface.

130. 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 first multifunctional crosslinker or the third multifunctional crosslinker with a second quaternary ammonium salt to form a second adduct; (c) combining the first adduct, and, if present, the second adduct, with a polyol and optionally a second multifunctional crosslinker to form an oil phase; (d) dissolving a water-soluble polymer in water to form an aqueous phase; (e) combining the oil phase and the water phase to form an oil-in-water emulsion; and (f) 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.

131. 131. The polymer or interpenetrating polymer network of claim 130, wherein a blocking agent is added to the oil phase after step (c) but before step (e).

132. 132. The polymer or interpenetrating polymer network of claim 130 or 131, wherein step (c) further comprises combining the first adduct, and, if present, the second adduct, with the polyol, and optionally the second multifunctional crosslinker, in an organic solvent or diluent to form the oil phase.

133. 133. The polymer or interpenetrating polymer network of any one of claims 130 to 132, wherein step (d) further comprises adding a chain extender to the oil phase or the water phase.

134. 134. The polymer or interpenetrating polymer network of any one of claims 130 to 133, wherein step (d) further comprises adding a surfactant to the aqueous phase.

135. 134. The polymer or interpenetrating polymer network of any one of claims 130-133, wherein step (d) further comprises adding a defoamer or antifoaming agent to the aqueous phase.

136. 134. The polymer or interpenetrating polymer network of any one of claims 130-133, wherein step (d) further comprises adding a surfactant and either a defoamer or antifoaming agent to the aqueous phase.

137. 137. The polymer or interpenetrating polymer network of any one of claims 130-136, wherein step (e) further comprises performing a direct emulsification process, wherein the emulsion is formed by vigorous shear and mixing.

138. 137. The polymer or interpenetrating polymer network of any one of claims 130-136, wherein step (e) further comprises performing a direct emulsification process, wherein the emulsion is formed by sonication.

139. 137. The polymer or interpenetrating polymer network of any one of claims 130-136, wherein step (e) 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.

140. 140. The polymer or interpenetrating polymer network of claim 139, 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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