EP4593601A1 - Compositions de revêtement antimicrobiennes - Google Patents

Compositions de revêtement antimicrobiennes

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Publication number
EP4593601A1
EP4593601A1 EP23786335.2A EP23786335A EP4593601A1 EP 4593601 A1 EP4593601 A1 EP 4593601A1 EP 23786335 A EP23786335 A EP 23786335A EP 4593601 A1 EP4593601 A1 EP 4593601A1
Authority
EP
European Patent Office
Prior art keywords
aryl
heteroalkyl
alkyl
polymer
antimicrobial composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP23786335.2A
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German (de)
English (en)
Inventor
Rong-Chang Liang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Polaroid IP BV
Original Assignee
Polaroid IP BV
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Filing date
Publication date
Application filed by Polaroid IP BV filed Critical Polaroid IP BV
Publication of EP4593601A1 publication Critical patent/EP4593601A1/fr
Pending legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/12—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • A01N25/10—Macromolecular compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides

Definitions

  • 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 transmissible by touching surfaces contaminated with the virus.
  • a 2020 study done at two major urban U.S. hospitals 1 concluded that there was a 36% decline in healthcare- associated infections when commonly touched surfaces (keyboards, countertops, railings, chairs, etc.) were coated with a disinfectant.
  • Desirable antimicrobial surface coatings would have the following properties: (i) broad spectrum antimicrobial activity at a low Minimum Inhibition Concentration (MIC); (ii) fast acting; (iii) long lasting; (iv) non-toxic and nonallergenic; (v) no materials leaching out Atty. Dkt. No. 130952-0701 of the coating; (vi) acceptable color, transparency and appearance as 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 appreciated by the inventors of the present application, conventional antimicrobial surface coatings lack many of the above-listed characteristics.
  • the embodiments of the present technology provide water-based quaternary ammonium polymeric coating formulations that can be applied to a wide range of surfaces to render them broadly antimicrobial.
  • the water-based coatings disclosed herein exhibit broad spectrum antimicrobial activity at a low Minimum Inhibition Concentration (MIC); (ii) are fast acting; (iii) long lasting; (iv) non-toxic and nonallergenic; (v) have no materials leaching out of the coating; (vi) have acceptable color, transparency and appearance as a surface coating; (vii) are easy to apply to a wide range of surfaces and materials; (viii) produce durable surface coatings that are resistant to water, alcohol and common solvents; and (ix) are easy and cost-effective to produce.
  • MIC Minimum Inhibition Concentration
  • a reactive low molecular-weight quaternary ammonium salt comprising a long-chain hydrophobic group that renders the salt with high surface activity and emulsification efficacy in water.
  • a reactive quaternary ammonium salt comprising a long-chain hydrophobic group that renders the salt with high surface activity and emulsification efficacy in water.
  • a multifunctional crosslinker such as a polyisocyanate
  • an oligomeric polyol and/or chain extender optionally an oligomeric polyol and/or chain extender
  • the resultant emulsion can be coated or sprayed onto a variety of surfaces or substrates while the chain extension or crosslinking reactions are continuing in the oil phase to form a highly durable antimicrobial coating after the film is dried and optionally post-cured.
  • the reactive low molecular-weight quaternary ammonium salt comprises a long-chain hydrophobic group on a nitrogen of the quaternary ammonium salt.
  • described herein is a use of a reactive water-soluble protective colloid that forms an interpenetration network with the antimicrobial polymers in the oil phase to further improve the durability of the resultant coating.
  • described herein is a use of a surface-active polyol in the oil phase to further improve the emulsion stability, reduce the particle size of the resultant emulsion, and improve the coating quality.
  • a surface-active polyol in the oil phase to further improve the emulsion stability, reduce the particle size of the resultant emulsion, and improve the coating quality.
  • Atty. Dkt. No. 130952-0701 in another aspect, described herein is a use of a blocking agent to protect the reaction product of the reactive surface-active quaternary ammonium salt with the multifunctional crosslinker before the emulsification step to further improve the emulsion stability and processability or green-time of the emulsion.
  • the blocking agent is de-blocked optionally in the presence of a catalyst or sensitizer, by for example, heat or radiation during or after the drying and/or post curing steps to obtain a durable coating.
  • a catalyst or sensitizer by for example, heat or radiation during or after the drying and/or post curing steps to obtain a durable coating.
  • the antimicrobial efficiency of organic solvent-based antimicrobial coatings generally decreases with an increasing crosslinking density of the coating.
  • a high degree of crosslinking is often required for acceptable coating properties including durability and resistance against organic solvents, alcohol, water, detergent and various disinfection solutions and processes.
  • the bioactive functional group in the organic solvent- based coatings tends to be trapped in the crosslinking network when the degree of crosslinking is high.
  • the high surface activity of the reactive quaternary ammonium salt of the present technology allows the bioactive functional group including quaternary ammonium group to diffuse to the interface of the emulsion droplet, and in turn the surface of the resultant coating.
  • durable coatings with desirable physical and chemical properties as well as a high antimicrobial efficiency can be achieved at the same time through use of the present technology.
  • an antimicrobial composition 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 to react with the first multifunctional crosslinker; a polyol; and optionally a second multifunctional crosslinker; and (ii) an aqueous phase comprising a water-soluble polymer.
  • the first quaternary ammonium salt has a chemical structure of , wherein R 1 is selected from a group consisting of -(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
  • x31 is an integer from 1 to 30 and y31 is an integer from 0 to 29, wherein x31 + y31 ⁇ 30; x40 is an integer from 1 to 19 and y40 is an integer from 1 to 19, wherein 3 ⁇ (x40 + y40) ⁇ 20; x41 is an integer from 1 to 20, and y41 is an integer from 0 to 19, wherein 3 ⁇ (x41 + y41) ⁇ 20; Y is selected from a group consisting of -OH, -NHR 4 , -SH, -CO 2 H, -C(O)NHR 4 , -C(S)NHR 4 , each R 4 is independently selected from a group consisting of 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
  • R 1 is selected from a group consisting of -(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); wherein -(C 12 -C 30 heteroalkyl), - (C 12 -C 30 heteroalkyl)-(C 6 -C 10 aryl), and -(C 6 -C 10 aryl)-(C 12 -C 30 heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S, and Si.
  • R 3 is selected from a group consisting of -(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); wherein -(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) have 1 to 4 heteroatoms independently selected from O, S, and Si.
  • R 2 and R 3 are methyl.
  • 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 is independently selected from a group consisting of 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), wherein -(C 6 -C 10 Atty.
  • Dkt. No. 130952-0701 aryl)-(C 1 -C 3 heteroalkyl) and -(C 1 -C 3 heteroalkyl)-(C 6 -C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si.
  • each R 5 is independently H or methyl.
  • 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.
  • 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.
  • 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.
  • the first multifunctional crosslinker which is incorporated into 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.
  • the first multifunctional crosslinker, 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.
  • 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.
  • 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.
  • the first multifunctional crosslinker is a first polyisocyanate
  • the second multifunctional crosslinker when present, is a second polyisocyanate, and the first polyisocyanate and the second polyisocyanate are different.
  • Atty. Dkt. No. 130952-0701 [0031]
  • the first multifunctional crosslinker is a first polyisocyanate
  • the second multifunctional crosslinker when present, is a second polyisocyanate, and the first polyisocyanate and the second polyisocyanate are the same.
  • each of the first and second polyisocyanates has an average isocyanate functionality of 2 to 5.
  • each of the first and second polyisocyanates has an average isocyanate functionality of 3 to 4.
  • each of the first and second polyisocyanates is prepared from a diisocyanate independently selected from a group consisting of hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), xylenediisocyanate (XDI), methylene-bis-(4-cyclohexylisocyanate) (H12MDI), meta-tetramethylxylene diisocyanate (TMXDI ), and trimethylhexamethylene diisocyanate (TMDI).
  • HDI hexamethylene diisocyanate
  • IPDI isophorone diisocyanate
  • TDI toluene diisocyanate
  • MDI methylene diphenyl diisocyanate
  • each of the first and second polyisocyanates is independently selected from a group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T series polyisocyanates, and LUPRANATE® M series polyisocyanates.
  • the first adduct has an average isocyanate functionality of 2 to 3.
  • the first adduct has an average isocyanate functionality of about 2.05 to about 2.3.
  • the reactive isocyanate functionality on the first adduct is protected with a blocking agent.
  • the blocking agent is selected from a group consisting of oximes, phenols, malonates, alcohols, lactams, dicarbonyl compounds, hydroxamates, bisulfite addition compounds, hydroxylamines, esters of p-hydroxybenzoic acid and salicylic acid.
  • the blocking agent is selected from a group consisting of acetone oxime, methyl ethyl ketone oxime, sodium bisulfite, diethyl malonate, and 3,5- dimethylpyrazole.
  • the antimicrobial composition further comprises a de-blocking agent. Atty. Dkt. No.
  • the de-blocking agent is selected from a group consisting of organotin, organobismuth, and tert-amines.
  • 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.
  • the oil phase further comprises an organic solvent or diluent.
  • the organic solvent or diluent in the oil phase is water miscible.
  • the organic solvent or diluent is acetone.
  • 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. [0048] In an aspect, 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.
  • the polyol is selected from a group consisting of polyether polyols, polyester polyols, polyacrylic polyols, polymethacrylic polyols, polycaprolactone polyols, polybutadiene polyols, poly(acrylonitrile-co-butadiene) polyols, polysiloxane polyols, a copolymer of any two or more thereof, and a combination of any two or more thereof.
  • the polyol is selected from a 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).
  • the polyol has a weight average molecular weight from about 300 to about 3000.
  • the polyol has a weight average molecular weight from about 400 to about 2000.
  • the polyol has a weight average molecular weight from about 600 to about 1500.
  • the polyol is 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. [0055] In an aspect, 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 an aspect, the water-soluble polymer is selected from a group consisting of hydroxyethyl cellulose (HEC), hydroxypropyl cellulose, polyvinyl alcohol, poly(hydroxyethyl methacrylate-co-alkyl methacrylate), poly(hydroxyethyl methacrylate-co-alkyl acrylate), Atty. Dkt. No.
  • the water-soluble polymer is hydroxyethyl cellulose or a hydrophobically modified derivative thereof.
  • the water-soluble polymer is a polyethylene imine.
  • the water-soluble polymer is present in the aqueous phase in amount of about 0.5% to about 15% by weight of the dry weight of the oil phase. [0060] In an aspect, the water-soluble polymer is present in the aqueous phase in amount of about 3% to about 12% by weight of the dry weight of the oil phase. [0061] In an aspect, the water-soluble polymer is present in the aqueous phase in amount of about 5% to about 10% by weight of the dry weight of the oil phase. [0062] In an aspect, in the antimicrobial composition, the aqueous phase further comprises a surfactant. [0063] In an aspect, the surfactant is a non-ionic surfactant.
  • the non-ionic surfactant has a HLB (hydrophilic-lipophilic balance) value of about 12 to about 15.
  • the non-ionic surfactant is selected from TRITON TM X-114 ((1,1,3,3-tetramethylbutyl)phenyl-polyethylene glycol), SILWET TM L-7604 (siloxane polyalkyleneoxide copolymer), and a combination thereof.
  • the surfactant is 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.
  • the surfactant is present in the aqueous phase in an amount of about 0.1% to about 1% by weight based on the dry weight of the oil phase.
  • the aqueous phase further comprises a defoamer or antifoamer.
  • the defoamer is FOAMSTAR ® ST 2410 (star polymer-based defoamer).
  • a random polymer or an interpenetrating polymer network is produced from random polymerization/crosslinking of the first adduct, the polyol, the water- soluble polymer, and, when present, the second multifunctional crosslinker. Atty. Dkt. No.
  • the oil phase further comprises a second adduct of the first multifunctional crosslinker and a second quaternary ammonium , wherein R 1a , R 2a , and R 3a are each independently methyl or ethyl;
  • a 1 is a linking group selected from a group consisting of -(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 -, wherein -(C 3 -C 20 heteroalkylene)- has 1 to 4 heteroatoms independently selected from O,
  • X- is independently acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, borate, or an organo-substituted derivative of any of the foregoing.
  • the oil phase further comprises a second adduct of a third multifunctional crosslinker and a second quaternary ammonium salt , wherein R 1a , R 2a , and R 3a are each independently methyl or ethyl;
  • a 1 is a linking group selected from a group consisting of -(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 -, wherein -(C 3 -C 20 heteroalkylene)- has 1 to 4 heteroatoms independently selected from O, S, and
  • the third multifunctional crosslinker is different from the first multifunctional crosslinker and, when present, from the second multifunctional crosslinker.
  • the third multifunctional crosslinker is a third polyisocyanate.
  • the third polyisocyanate has an average isocyanate functionality of 2 to 5.
  • the third polyisocyanate is prepared from a diisocyanate selected from a group consisting of hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), xylenediisocyanate (XDI), methylene-bis-(4-cyclohexylisocyanate) (H12MDI), meta- tetramethylxylene diisocyanate (TMXDI ), and trimethylhexamethylene diisocyanate (TMDI).
  • HDI hexamethylene diisocyanate
  • IPDI isophorone diisocyanate
  • TDI toluene diisocyanate
  • MDI methylene diphenyl diisocyanate
  • XDI xylenediisocyanate
  • H12MDI methylene-bis-(4-cycl
  • the third polyisocyanate is selected from a group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T series polyisocyanates, and LUPRANATE® M series polyisocyanates.
  • the second quaternary ammonium salt is .
  • 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.
  • 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.
  • the second adduct has an average isocyanate functionality of 2 to 3.
  • the second adduct has an average isocyanate functionality of about 2.05 to about 2.3. Atty. Dkt. No. 130952-0701
  • 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.
  • a random polymer or an interpenetrating polymer network is produced from random polymerization/crosslinking of the first adduct, the second adduct, the polyol, the water-soluble polymer, and, when present, the second multifunctional crosslinker.
  • the oil phase further comprises a chain extender selected from a group consisting of HO-(C n H 2n )-OH and HO-(C n H 2n-2 )-OH, or a combination thereof, wherein n is an integral between 2 and 8.
  • the chain extender is propanediol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexane dimethanol, or a combination of two or more thereof.
  • 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.
  • the chain extender is present in the oil phase in an amount of about 1% to about 5% by weight based on the dry weight of the oil phase.
  • a random polymer or an 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, when present, the second multifunctional crosslinker.
  • a polymer or interpenetrating polymer network comprising a 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, methylcellulose, 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 methacrylate), poly(hydroxyethyl acrylate-co-alkyl acrylate), poly(
  • the water-soluble polymer is present in the dried polymer or interpenetrating polymer network in an amount of about 0.5 wt.% to about 15 wt.%. Atty. Dkt. No. 130952-0701
  • the first quaternary ammonium salt has a chemical structure of , wherein R 1 is selected from a group consisting of -(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 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
  • R 1 is selected from a group consisting of -(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); wherein -(C 12 -C 30 heteroalkyl), -(C 12 -C 30 heteroalkyl)-(C 6 -C 10 aryl), and -(C 6 -C 10 aryl)-(C 12 -C 30 heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S, and Si.
  • R 3 is selected from a group consisting of -(C 1 -C 4 alkyl), -(C 1 -C 4 heteroalkyl), -(C 1 -C 4 alkyl)-(C 6 -C 10 Atty. Dkt. No.
  • R 2 and R 3 are methyl.
  • 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 is independently selected from a group consisting of 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), wherein -(C 6 -C 10 -C 10 aryl), wherein -(C 6 -C 10 -C 10 -C 10 aryl), wherein -(C 6 -
  • R 5 is H or methyl.
  • the first quaternary ammonium salt is , a combination of two or more thereof.
  • the first quaternary ammonium salt is present in the dried polymer or interpenetrating polymer network in an amount of about 10 wt.% to about 50 wt.%.
  • the first multifunctional crosslinker is a first polyisocyanate
  • the second multifunctional crosslinker when present, is a second polyisocyanate, and the first polyisocyanate and the second polyisocyanate are different.
  • the first multifunctional crosslinker is a first polyisocyanate
  • the second multifunctional crosslinker when present, is a second polyisocyanate, and the first polyisocyanate and the second polyisocyanate are the same.
  • each of the first and second polyisocyanates has an average isocyanate functionality of 2 to 5.
  • each of the first and second polyisocyanates has an average isocyanate functionality of 3 to 4.
  • each of the first and second polyisocyanates is prepared from a diisocyanate independently selected from a group consisting of hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), xylenediisocyanate (XDI), methylene-bis-(4-cyclohexylisocyanate) (H12MDI), meta- tetramethylxylene diisocyanate (TMXDI ), and trimethylhexamethylene diisocyanate (TMDI).
  • HDI hexamethylene diisocyanate
  • IPDI isophorone diisocyanate
  • TDI toluene diisocyanate
  • MDI methylene diphenyl diisocyanate
  • XDI xylenediisocyanate
  • H12MDI meta- te
  • each of the first and second polyisocyanates is independently selected from a group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T series polyisocyanates, and LUPRANATE® M series polyisocyanates.
  • the first multifunctional crosslinker is present in the dried polymer or interpenetrating polymer network in an amount of about 5 wt.% to about 25 wt.%.
  • the second multifunctional crosslinker is present in the dried polymer or interpenetrating polymer network in an amount of about 5 wt.% to about 25 wt.%.
  • each of the first polyisocyanate and the first adduct has an average isocyanate functionality of 2 to 3.
  • each of the first polyisocyanate and the first adduct has an average isocyanate functionality of about 2.05 to about 2.3.
  • the polyol is selected from a group consisting of polyether polyols, polyester polyols, polyacrylic polyols, polymethacrylic polyols, polycaprolactone polyols, polybutadiene polyols, poly(acrylonitrile- co-butadiene) polyols, polysiloxane polyols, a copolymer of any two or more thereof, and a combination of any two or more thereof.
  • the polyol is selected from a 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). Atty. Dkt. No. 130952-0701 [0112] In an aspect of the polymer or interpenetrating polymer network, the polyol has a weight average molecular weight from about 300 to about 3000.
  • the polyol has a weight average molecular weight from about 400 to about 2000.
  • the polyol has a weight average molecular weight from about 600 to about 1500.
  • the polyol is present in the dried polymer or interpenetrating polymer network in an amount of about 20 wt.% to about 40 wt.%.
  • the reagents further comprise a second adduct of the first multifunctional crosslinker and a second quaternary ammonium salt , wherein R 1a , R 2a , and R 3a are each independently methyl or ethyl;
  • a 1 is a linking group selected from a group consisting of -(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 -, wherein -(C 3 -C 20 heteroalkylene)- has
  • Y 1 is selected from a group consisting of -OH, -NHR 4a , -SH, -CO 2 H, -C(O)NHR 4a , - C ; each is independently selected from a group consisting of 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), wherein -(C 6 -C 10 aryl)-(C 1 -C 3 heteroalkyl) and -(C 1 -C 3 heteroalkyl)-(C 6 -C 10 aryl) have 1 to 4 heteroatoms independently selected
  • the reagents further comprise a second adduct of a third multifunctional crosslinker and a second quaternary ammonium salt , wherein R 1a , R 2a , and R 3a are each independently methyl or ethyl;
  • a 1 is a linking group selected from a group consisting of -(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 -, wherein -(C 3 -C 20 heteroalkylene)-,
  • x42 is an integer from 1 to 19 and y42 is an integer from 1 to 19, wherein 3 ⁇ (x42 + y42) ⁇ 20; x43 is an integer from 1 to 20, and y43 is an integer from 0 to 19, wherein 3 ⁇ (x43 + y43) ⁇ 20; Y 1 is selected from a group consisting of -OH, -NHR 4a , -SH, -CO 2 H, -C(O)NHR 4a , - C ; each R 4a is independently selected from a group consisting of 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), -(C 1 -C
  • the third multifunctional crosslinker is present in the dried polymer or interpenetrating polymer network in an amount of about 5 wt.% to about 25 wt.%.
  • the third multifunctional crosslinker is different from the first multifunctional crosslinker and, if present, from the second multifunctional crosslinker.
  • the third multifunctional crosslinker is a third polyisocyanate.
  • 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), xylenediisocyanate (XDI), methylene-bis-(4- cyclohexylisocyanate) (H12MDI), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).
  • HDI hexamethylene diisocyanate
  • IPDI isophorone diisocyanate
  • TDI toluene diisocyanate
  • MDI methylene diphenyl diisocyanate
  • XDI xylenediisocyanate
  • H12MDI meta-tetramethylxylene diis
  • the third polyisocyanate is selected from the group consisting of DESMODUR® N-3300, Atty. Dkt. No. 130952-0701 DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T series polyisocyanates, and LUPRANATE® M series polyisocyanates.
  • the second quaternary ammonium salt is (C2DMDEG-Br).
  • the second quaternary ammonium salt is present in the dried polymer or interpenetrating polymer network in an amount of about 1 wt.% to about 15 wt.%.
  • the second adduct has an average isocyanate functionality of 2 to 3.
  • the second adduct has an average isocyanate functionality of about 2.05 to about 2.3.
  • the reagents further comprise a chain extender selected from a group consisting of HO-(C n H 2n )-OH and HO-(C n H 2n-2 )-OH, or a combination thereof, wherein n is an integral between 2 and 8.
  • the chain extender is propanediol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexane dimethanol, or a combination of two or more thereof.
  • the chain extender is present in the dried polymer or interpenetrating polymer network in an amount of about 0.5 wt.% to about 10 wt.%.
  • a composition is provided comprising the polymer or interpenetrating polymer network described above.
  • an antimicrobial coating, coating fluid, or spraying fluid comprising the composition described above is provided.
  • a device, equipment, apparatus, or accessory is provided comprising the coating, the coating fluid or the spraying fluid described above.
  • the device, the equipment, the apparatus, or the accessory described above is provided, wherein the coating fluid or spraying fluid is water soluble or water dispersible. Atty. Dkt. No. 130952-0701 [0134] In an aspect, the device, the equipment, the apparatus, or the accessory as described above is provided, wherein the device, equipment, apparatus, or accessory is selected from a group consisting of a filter, an air purifier, and a mask.
  • the device, the equipment, the apparatus, or the accessory described above is provided, wherein the device, equipment, apparatus, or accessory is selected from a group consisting of a keyboard, a keypad, a stylus, a mouse, a handheld device, a remote controller, a touch screen, a phone, a handheld device, and a display.
  • a personal care aid comprising the coating, the coating fluid, or the spraying fluid described above is provided.
  • the coating fluid or the spraying fluid is water soluble or water dispersible.
  • a method to sanitize a surface is provided, the method comprising applying the composition described above.
  • a method to reduce antimicrobial growth on a surface comprising applying the composition described above to the surface.
  • a method to prevent antimicrobial growth on a surface is provided, the method comprising applying the composition described above to the surface.
  • a method as described above further comprises forming a coating solution containing the composition.
  • the foregoing method further comprises directing the coating solution to a surface, and providing a coating on the surface through the application of the coating solution to the surface.
  • a polymer or interpenetrating polymer network is prepared by: (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 a third multifunctional crosslinker with a second quaternary ammonium salt to form a second adduct; (c) combining the first adduct and, when 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 aqueous phase to form an oil-in-water emulsion; and Atty.
  • step (f) applying the emulsion onto a surface and allowing the emulsion to dry and cure on the surface to form the polymer or interpenetrating polymer network on the surface.
  • a blocking agent is added to the oil phase after step (c) but before step (e).
  • step (c) further comprises combining the first adduct and, when present, the second adduct, with the polyol and optionally the second multifunctional crosslinker in an organic solvent or diluent to form the oil phase.
  • step (d) further comprises adding a chain extender to the oil phase or the aqueous phase.
  • step (d) further comprises adding a surfactant to the aqueous phase.
  • step (d) further comprises adding a defoamer or antifoamer to the aqueous phase.
  • step (d) further comprises adding a surfactant and either a defoamer or antifoamer to the aqueous phase.
  • step (e) further comprises performing a direct emulsification process whereby the emulsion is formed by vigorous shear and mixing.
  • step (e) further comprises performing a direct emulsification process whereby the emulsion is formed by sonication.
  • step (e) further comprises performing a phase inversion emulsification process whereby a water-in-oil emulsion is first prepared, followed by phase inversion to form the oil-in-water emulsion.
  • the phase inversion is conducted by changing the phase ratio, temperature, surfactant, solvent, or any combination of two or more thereof.
  • the present technology provides a personal care aid comprising any of the above-described coating, coating fluid or spraying fluid.
  • the coating fluid or spraying fluid is water soluble or water dispersible.
  • Other implementations are also described and recited herein.
  • the term “approximately” or “about” in reference to a value or parameter are generally taken to include numbers that fall within a range of 5%, 10%, 15%, or 20% in either direction (greater than or less than) of the number unless otherwise stated or otherwise evident from the context (except where such number would be less than 0% or exceed 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, description referring to "about X” includes description of "X”.
  • the term “or” means “and/or.”
  • the term “and/or” as used in a phrase such as "A and/or B” herein is intended to include both A and B; A or B; A (alone); and B (alone).
  • the term “and/or” as used in a phrase such as "A, B, and/or C” 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).
  • the term “comprising” means that other elements can also be present in addition to the defined elements presented. The use of “comprising” indicates inclusion rather than limitation.
  • the term “consisting of” refers to compositions, methods, and respective components thereof as described herein, which are exclusive of any element not recited in that description of the embodiment. Atty. Dkt. No. 130952-0701
  • the term “consisting essentially of” refers to those elements required for a given embodiment. The term permits the presence of additional elements that do not materially affect the basic and novel or functional characteristic(s) of that embodiment of the present technology.
  • aryl refers to a carbocyclic (all carbon) ring that is fully aromatized.
  • An “aryl” group can be made up of two or more fused rings (rings that share two adjacent carbon atoms). When an aryl group is a fused ring system, then 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, without limitation, the radicals of benzene, naphthalene and azulene.
  • alkyl refers to a straight or branched chain fully saturated (no double or triple bonds) hydrocarbon group.
  • An alkyl group of the presently disclosed compounds may comprise from 1 to 15 carbon atoms.
  • An alkyl group herein may 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.
  • a C 1 -C 6 alkyl represents an alkyl group having 1 to 6 carbon atoms
  • a C 1 -C 4 alkyl represents an alkyl group having 1 to 4 carbon atoms
  • a C 1 -C 3 alkyl represents an alkyl group having 1 to 3 carbon atoms, etc.
  • alkyl groups include, without limitation, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl, t-butyl, amyl, t-amyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl.
  • alkoxy refers to an alkyl group, as defined above, appended to the parent molecular moiety through an oxy group, -O-.
  • a C 1 -C 6 alkoxy represents an alkoxy group containing 1 to 6 carbon atoms and a C 1 -C 3 alkoxy represents an alkoxy group containing 1 to 3 carbon atoms.
  • Representative examples of alkoxy include, but are not limited to, methoxy, ethoxy, propoxy, 2-propoxy, butoxy, tert-butoxy, pentyloxy, hexyloxy etc.
  • cycloalkyl refers to a monocyclic, bicyclic or polycyclic hydrocarbon ring system having, in some embodiments, 3 to 14 carbon atoms (e.g., C 3 -C 14 cycloalkyl), or 3 to 10 carbon atoms (e.g., C 3 -C 10 cycloalkyl), or 3 to 8 carbon atoms (e.g., C 3 - C 8 cycloalkyl), or 3 to 6 carbon atoms (e.g., C 3 -C 6 cycloalkyl) or 5 to 6 carbon atoms (e.g., C 5 -C 6 cycloalkyl).
  • 3 to 14 carbon atoms e.g., C 3 -C 14 cycloalkyl
  • 10 carbon atoms e.g., C 3 -C 10 cycloalkyl
  • 3 to 8 carbon atoms e.g., C 3 - C 8 cycloalkyl
  • 6 carbon atoms
  • 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.
  • monocyclic cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexeneyl, cyclohexynyl, cycloheptyl, cyclohepteneyl, cycloheptadieneyl, Atty. Dkt. No.
  • heteroalkyl refers to an alkyl group, as defined herein, in which one or more of the constituent carbon atoms have been replaced by nitrogen, oxygen, sulfur, or silicon.
  • a representative example of a heteroalkyl group is an alkoxy.
  • a heteroalkylene is a divalent heteroalkyl group.
  • heteroaryl refers to monocyclic or fused bicyclic aromatic groups (or rings) having, in some embodiments, from 5 to 14 (i.e., 5- to 14-membered heteroaryl), or from 5 to 10 (i.e., 5- to 10-membered heteroaryl), or from 5 to 6 (i.e., 5- to 6-membered heteroaryl) members (i.e., ring vertices), and containing from one to five, one to four, one to three, one to two or one heteroatom selected from nitrogen (N), oxygen (O), and sulfur (S).
  • N nitrogen
  • O oxygen
  • S sulfur
  • a heteroaryl group can be attached to the remainder of the molecule through a carbon atom or a heteroatom of the heteroaryl group, when chemically permissible.
  • heteroaryl groups include pyridyl, pyridazinyl, pyrazinyl, pyrimindinyl, triazinyl, purinyl, thienopyridinyl, thienopyrimidinyl, pyrazolopyrimidinyl, pyrazolopyridinyl, imidazopyridines, isothiazolyl, pyrazolyl, indazolyl, pteridinyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiadiazolyl, pyrrolyl, thiazolyl, furyl, thienyl and the like.
  • heterocycloalkyl refers to a non-aromatic monocyclic, bicyclic or polycyclic cycloalkyl ring having, in some embodiments, 3 to 14 members (e.g., 3- to 14- membered heterocycle), or 3 to 10 members (e.g., 3- to 10-membered heterocycle), or 3 to 8 members (e.g., 3- to 8-membered heterocycle), or 3 to 6 members (e.g., 3- to 6-membered heterocycle), or 5 to 6 members (e.g., 5- to 6-membered heterocycle), and having from one to five, one to four, one to three, one to two or one heteroatom selected from nitrogen (N), oxygen (O), sulfur (S) and silicon (Si).
  • 3 to 14 members e.g., 3- to 14- membered heterocycle
  • 3 to 10 members e.g., 3- to 10-membered heterocycle
  • 3 to 8 members e.g., 3- to 8-membered heterocycle
  • 3 to 6 members
  • 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.
  • 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, when chemically permissible.
  • Atty. Dkt. No. 130952-0701 “independently selected” indicates that each one of a designated group is selected independently from a subsequent list of species.
  • the term “statistically significant” or “significantly” refers to statistical significance and generally means a two standard deviation (2SD) or greater difference.
  • the terms “decrease”, “reduced”, “reduction”, or “inhibit” are all used herein to mean a decrease by a statistically significant amount.
  • “reduce,” “reduction” or “decrease” or “inhibit” typically means a decrease by at least 10% as compared to a reference level (e.g., the absence of a given treatment or agent) and can include, for example, a decrease by 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.
  • “reduction” or “inhibition” does not encompass a complete inhibition or reduction as compared to a reference level. “Complete inhibition” is a 100% inhibition as compared to a reference level. A decrease can be preferably down to a level accepted as within the range of normal for an individual without a given disorder. [0174] The terms “increased”, “increase”, “enhance”, or “activate” are all used herein to mean an increase by a statically significant amount.
  • the terms “increased”, “increase”, “enhance”, or “activate” can mean an increase of at least 10% as compared to a reference level, for example an increase of at least about 20%, or at least about 30%, or at least about 40%, or at least about 50%, or at least about 60%, or at least about 70%, or at least about 80%, or at least about 90% or up to and including a 100% increase or any increase between 10-100% as compared to a reference level, or at least about a 2-fold, or at least about a 3-fold, or at least about a 4-fold, or at least about a 5-fold or at least about a 10-fold increase, or any increase between 2-fold and 10-fold or greater as compared to a reference level.
  • polyisocyanates generally represents the family of polyisocyanates containing more than one isocyanate reactive group such as, but not limited to, DESMODUR® N3300 and N100 (made by Covestro GmbH 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)- Atty.
  • DESMODUR® N3300 and N100 made by Covestro Deutschland AG of Leverkusen, Germany
  • HDI hexamethylene diisocyanate
  • DESMODUR® Z4470SN made by Covestro Deutschland AG of Leverkusen, Germany
  • antimicrobial is used generally to indicate at least some level of microbe kill by a composition or a coating on a portion of a surface.
  • antimicrobial may be used to indicate a biostatic efficacy, sanitizing 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).
  • Microbes, or microorganisms may include any species of bacteria, virus, fungus including mold and yeast, or spore.
  • antimicrobial herein encompasses antiviral, antibacterial and antifungal.
  • the terms "residual antimicrobial,” “residual self-sanitizing,” and “self-decontaminating surface” are used interchangeably to indicate a surface that maintains antimicrobial efficacy over a certain period of time under certain conditions once the surface is coated with an antimicrobial coating composition and that composition dried on the surface as a thin film.
  • a coated surface may maintain residual antimicrobial efficacy indefinitely, or the coating may eventually "wear out” and lose its residual antimicrobial efficacy.
  • An antimicrobial coating composition may function as a contact sanitizer, bacteriostatic material, disinfectant, or sterilant, (e.g., as a liquid antimicrobial applied to a contaminated surface) and may also have the ability to leave behind a residual antimicrobial coating on the surface once dried or cured thereon that can keep inactivating new microorganisms that contact the coated surface.
  • coating compositions may not be antimicrobial until dried or cured on a surface but are still referred to as antimicrobial coating compositions because of their ability to produce a residual antimicrobial coating on a surface.
  • Antimicrobial coating compositions for use in various embodiments may provide a residual antimicrobial efficacy to a surface, meaning that a microorganism later inoculated on, or that otherwise comes in contact with, the coated surface may experience cell death, destruction, or inactivation.
  • the residual antimicrobial effect made possible by the coatings herein is not limited by a particular mechanism of action, and no such theories are proffered.
  • an antimicrobial effect measured on a surface may be the result of intracellular mutations, inhibition of certain cellular processes, rupture of a cell wall, or a nondescript inactivation of the organism, such as in the case of viruses.
  • Other antimicrobial effects may include inhibiting the reproduction of an organism or inhibiting the organism's ability to accumulate into biofilms.
  • the term "antimicrobial coating composition” refers to a chemical composition comprising at least one chemical species, which is used to produce a residual antimicrobial coating on a surface after the composition is applied and then either dried, allowed to dry, or cured in some manner.
  • the term is also used for liquid Atty. Dkt. No. 130952-0701 compositions that may find use as a germicidal spray (disinfectant or sanitizer), since the composition could then go on to dry into an antimicrobial coating.
  • compositions that may be applied sequentially (e.g., over or under) or contemporaneously with the application of an antimicrobial coating composition, such as to assist in bonding the residual antimicrobial coating to the surface, improve durability of the overall coating, and/or to provide a catalytic effect or some sort of potentiation or synergy with the residual antimicrobial coating comprising an antimicrobial active.
  • an antimicrobial coating composition each one of multiple compositions used sequentially or contemporaneously to produce an overall residual antimicrobial coating on a portion of a surface is referred to as an "antimicrobial coating composition," even if one or more of the compositions used for coating has no identifiable antimicrobial activity or where the active agent is uncertain.
  • An antimicrobial coating composition may comprise a neat, 100% active chemical species or may be a solution or suspension of a single chemical species in a solvent.
  • a composition may comprise a complex mixture of chemical substances, some of which may chemically react (hydrolyze, self-condense, etc.) within the composition to produce identifiable or unidentifiable reaction products.
  • a monomeric chemical species in an antimicrobial coating composition may partially or fully polymerize or copolymerize, such as to produce polymers including homopolymer and copolymers with a distribution of molecular weight, comonomer ratio, or molecular architecture while in solution, prior to a coating process using that composition.
  • chemical constituents within an antimicrobial coating composition may chemically react, graft, or form an interpenetration network on the surface or interphase that the composition is applied to, such as while the composition is drying and concentrating on the surface or while the coating composition is cured by various methods.
  • a solution comprising a polymer distribution may polymerize or cure further, such as to longer chain lengths or forming a polymer network, while the solution dries on a surface.
  • Antimicrobial coating compositions for use in various embodiments may further comprise any number and combination of inert excipients, such as for example, solvents, buffers, acids, alkali, surfactants, emulsifiers, stabilizers, UV absorbers, thickeners, free-radical initiators, fillers, pigments or colorants, catalysts, etc.
  • inert excipients such as for example, solvents, buffers, acids, alkali, surfactants, emulsifiers, stabilizers, UV absorbers, thickeners, free-radical initiators, fillers, pigments or colorants, catalysts, etc.
  • a homopolymer distribution herein may include the dimer and above, or the trimer and above, as indicated.
  • a homopolymer chain length distribution may be well defined and characterized, and in other instances, the distribution may not be Atty. Dkt. No. 130952-0701 characterizable at all and may remain unknown.
  • copolymer herein includes random copolymer, block copolymer, graft copolymer, interpolymer complex, interpenetration network, etc., and their blends.
  • wt.% takes on the ordinary meaning of percent (%) by weight of an ingredient in a chemical composition, based on the total weight of the composition "as made.”
  • an aqueous composition comprising 1 wt. % amine "based on the total weight of the composition” equates to a composition containing 99.0 grams water and 1.0 gram amine.
  • Wt. % in a composition indicates the wt. % of active material, unless indicated otherwise.
  • “As made” means that a written composition shows what was added to a mixing vessel, and not what might end up in the mixture after certain ingredients react, such as if an ingredient hydrolyzes or polymerizes.
  • ANTIMICROBIAL COATINGS Surfaces of objects which are in direct or indirect contact with humans and animals are exposed to a high microbial load and have a demonstrable influence on the transmission of diseases and infections.
  • the antimicrobial coatings of the present technology can be particularly useful because they can be applied to just about any surface and drastically 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, pulling handles, and grips; parts such as faucet handles for Atty. Dkt. No.
  • Staph is a group of over 30 strains that cause many different types of infections, including skin infections, food and blood poisoning. Most strains of E. coli are not harmful but are part of the healthy bacterial flora in the human gut. However, some strains can cause various diseases, including pneumonia, urinary tract infections, diarrhea and meningitis. Some strains of E. coli can also cause nausea, vomiting and fever. MRSA is a type of bacterium that causes infections in different parts of the body.
  • VRE ulcerative colitis
  • Enterococci a type of bacteria called Enterococci that have developed resistance to many antibiotics, especially Vancomycin as the name suggests. These bacteria can cause serious infections, especially in people who are already ill, weak, and/or immunocompromised. VRE may cause bloodstream infection (sepsis), urinary infection, pneumonia, heart infections (endocarditis), or meningitis.
  • 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) as these viruses have been demonstrated to have long survival periods on numerous surfaces. For example, in a recent study of airports, 15 detection of pathogen viral nucleic acids demonstrated viral surface contamination at multiple sites associated with high touch rates and suggested a potential risk in standard passenger pathways at airport sites. These viruses can cause serious infections, especially in people who are already ill, weak, and/or immunocompromised.
  • Atty. Dkt. No. 130952-0701 such formulations are not entirely satisfactory, as they only lead to a 3 log reduction that fails to completely inhibit regrowth of bacteria. This lack of effectiveness can probably be attributed to the fact that silver is used insufficient amounts and/or is unevenly dispersed throughout the composition, resulting in an inconsistent and, ultimately, ineffective distribution of anti-microbial particles within the composition/coating. [0189] Park et al. (2006) 17 reported antimicrobial active polymers made by reacting polyethyleneimine with a hydrophobic long chain hydrocarbon alkylating agent and then quaternization by methylation.
  • the coatings are not colorless, and they are not durable and resistant to contact with water and other common solvents to which the surface may regularly come in contact.
  • the antiviral activity of quaternary ammonium polymers is due to the interaction between the hydrophobic quaternary ammonium groups and the negatively charged membrane of the virus causing a disruption of the membrane which inactivates microorganisms such as viruses.
  • the active ingredients in many of the commercially-available antiviral surface sprays are low molecular weight quaternary ammonium surfactant-like materials, which are assumed to act by this mechanism but that do not form long lasting durable surface coatings.
  • a polymer or interpenetrating polymer network comprising a 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.
  • the water-soluble polymer comprises, consists essentially of, or consists of hydroxyethyl cellulose, hydroxypropyl cellulose, methylcellulose, 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), polyethylene imine, 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 with poly(glycidyl methacrylate).
  • a polymer or interpenetrating polymer network comprising a 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, wherein the water-soluble polymer comprises, consists essentially of, or consists of hydroxyethyl cellulose, hydroxypropyl cellulose, methylcellulose, 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 methacrylate),
  • the water-soluble polymer may be present in the dried polymer or interpenetrating polymer network in an amount of from about 0.5 wt.% to about 15 wt.%. This includes 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 wt.%, or any value therebetween.
  • the water-soluble polymer is present in the dried polymer or Atty. Dkt. No.
  • 130952-0701 interpenetrating polymer network in an amount of from about 0.5 wt.% to about 15 wt.%, about 3 wt.% to about 12 wt.%, or about 5 wt.% to about 10 wt.%.
  • the first quaternary ammonium salt may have a chemical structure of: wherein: R 1 is selected from a group consisting of -(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-; wherein - (C 8 -C 30 heteroalkyl), -(C 8 -C 30 heteroalkyl)
  • R 1 is selected from a group consisting of -(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); wherein -(C 12 -C 30 heteroalkyl), -(C 12 -C 30 heteroalkyl)-(C 6 -C 10 aryl), and -(C 6 -C 10 aryl)-(C 12 -C 30 heteroalkyl) have 1 to 4 heteroatoms independently selected from O, S, and Si.
  • R 1 is - (C 12 -C 30 alkyl). In some embodiments, R 1 is -(C 8 -C 30 heteroalkyl) with 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 1 is -(C 6 -C 10 aryl)-(C 12 - C 30 alkyl). In some embodiments, R 1 is -(C 12 -C 30 alkyl)-(C 6 -C 10 aryl). In some embodiments, R 1 is -(C 6 -C 10 aryl)-(C 12 -C 30 heteroalkyl) with 1 to 4 heteroatoms independently selected from O, S, and Si.
  • R 1 is -(C 12 -C 30 heteroalkyl)-(C 6 -C 10 aryl) with 1 to 4 Atty. Dkt. No. 130952-0701 heteroatoms independently selected from O, S, and Si.
  • R 1 is - (CR m R n ) x10 -W 10 -(CR p R q ) y10 -H.
  • R 1 is -(CR m R n ) x11 -W 11 -(CR p R q ) y11 -H.
  • R 2 is -(C 1 -C 4 alkyl).
  • R 2 is -(C 1 - C 4 heteroalkyl) with 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 2 is -(C 6 -C 10 aryl)-(C 1 -C 4 alkyl). In some embodiments, R 2 is -(C 1 -C 4 alkyl)- (C 6 -C 10 aryl). In some embodiments, R 2 is -(C 6 -C 10 aryl). In some embodiments, R 2 is -(C 6 - C 10 aryl)-(C 1 -C 4 heteroalkyl) with 1 to 4 heteroatoms independently selected from O, S, and Si.
  • R 2 is -(C 1 -C 4 heteroalkyl)-(C 6 -C 10 aryl) with 1 to 4 heteroatoms independently selected from O, S, and Si.
  • R 2 is -(CR m R n ) x20 -W 20 - (CR p R q ) y20 -H.
  • R 2 is -(CR m R n ) x21 -W 21 -(CR p R q ) y21 -H.
  • R 3 is selected from a group consisting of -(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); wherein -(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) have 1 to 4 heteroatoms independently selected from O, S, and Si.
  • R 3 is -(C 1 -C 4 alkyl). In some embodiments, R 3 is -(C 1 -C 4 heteroalkyl) with 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 3 is -(C 6 -C 10 aryl)-(C 1 -C 4 alkyl). In some embodiments, R 3 is -(C 1 -C 4 alkyl)-(C 6 -C 10 aryl). In some embodiments, R 3 is - (C 6 -C 10 aryl)-(C 1 -C 4 heteroalkyl) with 1 to 4 heteroatoms independently selected from O, S, and Si.
  • R 3 is -(C 1 -C 4 heteroalkyl)-(C 6 -C 10 aryl) with 1 to 4 heteroatoms independently selected from O, S, and Si.
  • R 3 is - (CR m R n ) x30 -W 30 -(CR p R q ) y30 -H.
  • R 3 is -(CR m R n ) x31 -W 31 -(CR p R q ) y31 -H.
  • R 2 and R 3 are methyl.
  • R 1 is C 12 -C 30 alkyl, and R 2 and R 3 are methyl.
  • A is -(C 3 -C 20 alkylene)- optionally substituted with 1 to 6 substituents independently selected from -(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).
  • A is -(C 3 -C 20 heteroalkylene)- with 1 to 4 heteroatoms independently selected from O, S, and Si, and optionally substituted with 1 to 6 substituents independently selected from -(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 ary).
  • A is - (C 6 -C 10 arylene)-(C 3 -C 20 alkylene)-. In some embodiments, A is -(C 3 -C 20 alkylene)-(C 6 -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 -.
  • 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 is independently selected from Atty. Dkt. No.
  • 130952-0701 a group consisting of 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), wherein -(C 6 -C 10 aryl)-(C 1 -C 3 heteroalkyl) and -(C 1 -C 3 heteroalkyl)-(C 6 -C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si.
  • R 5 is H or methyl.
  • Y is -OH. In some embodiments, Y is -NHR 4 . In some embodiments, Y is -SH. In some embodiments, Y is -CO 2 H.
  • Y is - C(O)NHR 4 , wherein R 4 is selected from a group consisting of 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), wherein -(C 6 -C 10 aryl)-(C 1 -C 3 heteroalkyl) and -(C 1 -C 3 heteroalkyl)-(C 6 -C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si.
  • Y is -C(S)NHR 4 , wherein R 4 is selected from a group consisting of 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), wherein -(C 6 -C 10 aryl)-(C 1 -C 3 heteroalkyl) and - (C 1 -C 3 heteroalkyl)-(C 6 -C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si.
  • Y is , wherein each R 4 is independently selected from a group consisting of 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), wherein -(C 6 -C 10 aryl)-(C 1 -C 3 heteroalkyl) and -(C 1 -C 3 heteroalkyl)-(C 6 -C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si.
  • Y is , wherein each R 4 is independently selected from a group consisting of 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), wherein -(C 6 -C 10 aryl)-(C 1 -C 3 heteroalkyl) and -(C 1 -C 3 heteroalkyl)-(C 6 -C 10 aryl) have 1 to 4 heteroatoms independently selected from O, S, and Si.
  • X- may be independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, and borate, and their organo-substituted derivatives.
  • organo-substituted derivatives refers to anions wherein a sulfur atom, a phosphorous atom, a boron atom, a silicon atom or carbonyl group is substituted with either an alkyl or an aryl group.
  • Non-limiting examples include methylsulfate, methanesulfonate, p-toluene sulfonate, trifluoromethylsulfonate, and trifluoroacetate.
  • Atty. Dkt. No. 130952-0701 the first quaternary ammonium salt is , , or a combination of two or more thereof.
  • the first quaternary ammonium salt may be present in the dried polymer or interpenetrating polymer network in an amount of about 10 wt.% to about 50 wt.%.
  • the first quaternary ammonium salt is present in the dried polymer or interpenetrating polymer network in an amount of about 15 wt.% to about 40 wt.%. In some embodiments, the first quaternary ammonium salt is present in the dried polymer or interpenetrating polymer network in an amount of about 20 wt.% to about 35 wt.%.
  • the amount of quaternary ammonium salt may be represented by millinormal/g (mN/g) instead of wt.% based on the total weight of the dried polymer or interpenetrating polymer network.
  • the first quaternary ammonium salt may be present in the dried polymer or interpenetrating polymer network in an amount of from about 0.3 mN/g to about 1.0 mN/g. This includes 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, or 1.0 mN/g, or any value therebetween.
  • the first quaternary ammonium salt is present in the dried polymer or interpenetrating polymer network in an amount of from about 0.4 mN/g to about 0.9 mN/g. In some embodiments, the first quaternary ammonium salt is present in the dried polymer or interpenetrating polymer network in an amount of from about 0.5 mN/g to about 0.8 mN/g.
  • the first multifunctional crosslinker may be a first polyisocyanate. In some embodiments, the first polyisocyanate has an average isocyanate functionality of 2 to 5. This includes an average isocyanate functionality of 2, 3, 4, or 5.
  • the first polyisocyanate has an average isocyanate functionality of 3 to 4.
  • the second multifunctional crosslinker may be a second polyisocyanate. In some embodiments, the second polyisocyanate has an average isocyanate functionality of 2 to 5. This includes 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, when present, is a second Atty. Dkt. No. 130952-0701 polyisocyanate, wherein the first polyisocyanate and the second polyisocyanate are different.
  • the first multifunctional crosslinker is a first polyisocyanate
  • the second multifunctional crosslinker when present, is a second polyisocyanate, wherein the first polyisocyanate and the second polyisocyanate are the same.
  • first and second polyisocyanates may be prepared from diisocyanates independently selected from the group consisting of: hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), xylenediisocyanate (XDI), methylene-bis-(4- cyclohexylisocyanate) (H12MDI), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).
  • HDI hexamethylene diisocyanate
  • IPDI isophorone diisocyanate
  • TDI toluene diisocyanate
  • MDI methylene diphenyl diisocyanate
  • XDI xylenediisocyanate
  • H12MDI methylene-bis-(4-
  • one or both 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.
  • 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 toluene diisocyanate (TDI)-based aromatic polyisocyanates.
  • LUPRANATE® M series polyisocyanates are 4,4- diphenylmethane diisocyanate (MDI)-based aromatic polyisocyanates.
  • the first multifunctional crosslinker may be present in the dried polymer or interpenetrating polymer network in an amount of about 5 wt.% to about 25 wt.%. This includes 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 wt.%, or any value therebetween.
  • the first multifunctional crosslinker is present in the dried polymer or interpenetrating polymer network in an amount of about 7 wt.% to about 15 wt.%, or about 5 wt.% to about 20 wt.%.
  • the second multifunctional crosslinker may be present in the dried polymer or interpenetrating polymer network in an amount of about 5 wt.% to about 25 wt.%, This includes 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 wt.%, or any value therebetween.
  • the second multifunctional crosslinker is present in the dried polymer or interpenetrating polymer network in an amount of about 10 wt.% to about 20 wt.%, or about 5 wt.% to about 20 wt.%.
  • 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.
  • the polyol may be selected from a group consisting of polyether polyols, polyester polyols, polyacrylic polyols, polymethacrylic polyols, polycaprolactone polyols, Atty. Dkt. No.
  • 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 a copolymer of one or more thereof with polyester, polycaprolactone, polybutadiene, poly(acrylonitrile-butadiene), polysiloxane, or polyacrylate.
  • PTMG polytetramethylene glycol
  • PEG polyethylene glycol
  • PPG polypropylene glycol
  • the polyol is selected from a 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).
  • the polyol comprises, consists essentially of, or consists of a polyether polyol, a polyester polyol, or a combination thereof.
  • the polyol may have an average molecular weight of about 300 to about 3000 daltons.
  • the polyol has an average molecular weight of about 400 to about 2000, or about 600 to about 1500 daltons.
  • the polyol may be present in the dried polymer or interpenetrating polymer network in an amount of about 15 wt.% to about 60 wt.%.
  • the polyol is present in the dried polymer or interpenetrating polymer network in an amount of about 20 wt.% to about 40 wt.%. [0224] In some embodiments, the polyol is pre-reacted with the second polyisocyanate to form an isocyanate end-capped prepolymer.
  • the reagents may further comprise a second adduct of (i) the first multifunctional crosslinker or a third multifunctional crosslinker; and (ii) a second quaternary ammonium salt , wherein R 1a , R 2a , and R 3a are each independently methyl or ethyl;
  • a 1 is a linking group selected from a group consisting of -(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 -, wherein -(C 3 -C 20 heteroalkylene)- has 1
  • the third multifunctional crosslinker may be present in the dried polymer or interpenetrating polymer network in an amount of about 5 wt.% to about 25 wt.%. This includes 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 wt.%, or any value therebetween. In some embodiments, the third multifunctional crosslinker is present in the dried polymer or interpenetrating polymer network in an amount of about 7 wt.% to about 15 wt.%, or about 5 wt.% to about 20 wt.%. [0227] The third multifunctional crosslinker may be different from the first multifunctional crosslinker and, if present, from the second multifunctional crosslinker.
  • the third multifunctional crosslinker is a third polyisocyanate.
  • the third polyisocyanate is prepared from a Atty. Dkt. No. 130952-0701 diisocyanate selected from the group consisting of: hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylene diphenyl diisocyanate (MDI), xylenediisocyanate (XDI), methylene-bis-(4-cyclohexylisocyanate) (H12MDI), meta- tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).
  • HDI hexamethylene diisocyanate
  • IPDI isophorone diisocyanate
  • TDI toluene diisocyanate
  • MDI methylene diphenyl diisocyan
  • 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.
  • the second quaternary ammonium salt is salt may be present in the dried polymer or interpenetrating polymer network in an amount of about 1 wt.% to about 15 wt.%. This includes about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 wt.%, or any value therebetween.
  • the second adduct has an average isocyanate functionality of 2 to 3.
  • the second adduct has an average isocyanate functionality of 2.05 to about 2.3.
  • the reagents may further comprise a chain extender selected from a group consisting of HO-(C n H 2n )-OH and HO-(C n H 2n-2 )-OH, or a combination thereof, wherein n is an integral between 2 and 8.
  • the chain extender is propanediol, 1,4- butanediol, neopentyl glycol, hexanediol, cyclohexane dimethanol, or a combination of two or more thereof.
  • the chain extender may be present in the dried polymer or interpenetrating polymer network in an amount of about 0.5 wt.% to about 10 wt.%. This includes about 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 wt.%, or any value therebetween.
  • a polymer or interpenetrating polymer network comprising a 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 second adduct of (a) the first multifunctional crosslinker or a third multifunctional crosslinker, and (b) a second quaternary ammonium salt; and (vi) optionally a chain extender.
  • a polymer or interpenetrating polymer network comprising a 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 second adduct of (a) the first Atty. Dkt. No.
  • the water-soluble polymer comprises, consists essentially of, or consists of hydroxyethyl cellulose, hydroxypropyl cellulose, methylcellulose, 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), polyethylene imine, 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
  • a first quaternary ammonium salt reacts with a first polyisocyanate to form a first adduct, wherein the first adduct retains unreacted isocyanate functionality from the first polyisocyanate.
  • about 10% to about 40%, preferably about 25% to about 33% of isocyanate functionality on the first polyisocyanate is converted to, for example, urethane or urea by reaction with the first quaternary ammonium salt.
  • the unreacted isocyanate functionality subsequently reacts with one or more of the polyol, the chain extender (if present), water, and the water-soluble polymer (if reactive).
  • the second quaternary ammonium salt reacts with the first polyisocyanate or a third polyisocyanate to form a second adduct, wherein the second adduct retains unreacted isocyanate functionality from the first or third polyisocyanate.
  • about 10% to about 40%, preferably about 25% to 33% of isocyanate functionality on the first polyisocyanate is converted to, for example, urethane or urea by reaction with the second quaternary ammonium salt.
  • the second multifunctional crosslinker and/or second adduct may also react with one or more of the polyol, the chain extender (if present), water, and the water-soluble polymer (if reactive).
  • a polymer or interpenetrating polymer network is prepared by (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 a third multifunctional crosslinker with a second quaternary ammonium salt to form a second adduct; (c) combining the first adduct and, when 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 aqueous phase to form an oil-in-water emulsion; and Atty.
  • step (f) applying the emulsion onto a surface and allowing the emulsion to dry and cure on the surface to form the polymer or interpenetrating polymer network on the surface.
  • a blocking agent is added to the oil phase after step (c) but before step (e).
  • step (c) further comprises combining the first adduct and, when present, the second adduct, with the polyol and optionally the second multifunctional crosslinker in an organic solvent or diluent to form the oil phase.
  • step (d) further comprises adding a chain extender to the oil phase or aqueous phase.
  • step (d) further comprises adding a surfactant to the aqueous phase. In some embodiments, step (d) further comprises adding a defoamer or antifoamer to the aqueous phase. In some embodiments, step (d) further comprises adding a surfactant and either a defoamer or antifoamer to the aqueous phase. [0241] In some embodiments, step (e) further comprises performing a direct emulsification process whereby the emulsion is formed by vigorous shear and mixing. In some embodiments, step (e) further comprises performing a direct emulsification process whereby the emulsion is formed by sonication.
  • step (e) further comprises performing a phase inversion emulsification process whereby a water-in-oil emulsion is first prepared, followed by phase inversion to form the oil-in-water emulsion.
  • the phase inversion may be conducted by, for example, changing the phase ratio, temperature, surfactant, solvent, or any combination of two or more thereof.
  • a multiphase water-in-oil-in-water emulsion is formed prior to conversion to the oil-in-water emulsion in step (e).
  • combining the oil phase and the aqueous phase in step (e) forms a combination of the oil-in-water emulsion and a multiphase water-in-oil-in- water emulsion.
  • reagents for the preparation of a polymer or interpenetrating polymer network described herein are comprised in an antimicrobial composition.
  • an antimicrobial composition comprising an oil-in-water emulsion, wherein the oil-in-water emulsion comprises (i) an oil phase comprising Atty. Dkt. No.
  • This composition may be applied to a surface and allowed to dry and cure, thereby forming a polymer or interpenetrating polymer network of the present technology.
  • the water-soluble polymer may be a reactive water-soluble polymer and crosslinks with one or both of the first adduct and the second multifunctional crosslinker.
  • the water-soluble polymer is a reactive water-soluble polymer and 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.
  • the reactive linking group of the first quaternary ammonium salt may be selected from a group consisting of -OH, -NHR 4 , -SH, -CO 2 H, -C(O)NHR 4 , -C(S)NHR 4 , , wherein each R 4 is independently selected from a group consisting of 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), -(C 1
  • the first quaternary ammonium salt, incorporated into 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.
  • dry weight of the oil phase refers to weight of the oil phase in the absence of any organic solvent and any water.
  • the first multifunctional crosslinker (e.g., the first polyisocyanate), incorporated into the first adduct, may be present in the oil phase in an amount of about 5% to about 25% by weight based on the dry weight of the oil phase. This includes about 5%, Atty. Dkt. No. 130952-0701 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.
  • Reaction with the blocking agent converts the reactive isocyanate functionality to blocked isocyanates (i.e., the isocyanate group is reversibly protected from immediate reaction with a nucleophile). This decreases the rate of polyisocyanate reaction with water in a subsequent emulsification step and/or the cross-linking reaction with, for example, any polyol(s) in the oil phase and/or the water-soluble polymer (such as hydroxyethyl cellulose) in the aqueous phase.
  • the coatability and process window of the coating process are also significantly improved.
  • the defect rate of resultant surface coatings is reduced and the yield rate of coated products is also improved.
  • no blocking agent is used in order to provide a more rapidly curing coating.
  • the blocking agent is selected from a group consisting of oximes, phenols, malonates, alcohols, lactams, dicarbonyl compounds, hydroxamates, bisulfite addition compounds, hydroxylamines, esters of p-hydroxybenzoic acid and salicylic acid.
  • the blocking agent is selected from a group consisting of acetone oxime, methyl ethyl ketone oxime, sodium bisulfite, diethyl malonate, and 3,5- dimethylpyrazole.
  • the composition further comprises a de-blocking agent.
  • the de-blocking agent includes, but is not limited to, organotin, organobismuth, and tert-amines. Non-limiting examples include triethanolamine; N,N,N’N’-tetrakis(2- hydroxyethyl) ethylene diamine; and K-KAT XK-651 (bismuth carboxylate catalyst).
  • 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 about 15%, Atty. Dkt. No.
  • 130952-0701 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.
  • the first adduct is present in an amount of about 15% to about 65%, about 15% to about 60%, about 15% to about 50%, about 20% to about 70%, about 20% to about 60%, or about 20% to about 50%, by weight based on the dry weight of the oil phase.
  • the oil phase further comprises a second adduct as described herein.
  • the second adduct 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.
  • the second quaternary ammonium salt, incorporated into 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.
  • the second quaternary ammonium salt, incorporated into 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.
  • the third multifunctional crosslinker e.g., the third polyisocyanate
  • incorporated into the second adduct may be present in the oil phase in an amount of about 5% to about 25% by weight based on the dry weight of the oil phase.
  • the third multifunctional crosslinker e.g., the third polyisocyanate
  • the third 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.
  • the oil phase further comprises a chain extender selected from a group consisting of HO-(C n H 2n )-OH and HO-(C n H 2n-2 )-OH, or a combination thereof, wherein n is an integral between 2 and 8.
  • the chain extender is propanediol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexane dimethanol, 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.
  • the chain extender is present in the oil phase in Atty. Dkt. No. 130952-0701 an amount of about 0.5% to about 10%, or about 1% to about 5% by weight based on the dry weight of the oil phase.
  • the oil phase further comprises an organic solvent or diluent.
  • the organic solvent or diluent in the oil phase is water miscible.
  • the organic solvent or diluent is acetone.
  • 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. This includes about 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, or 35%, or any value therebetween. In some embodiments, 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.
  • 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. This includes 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.
  • 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.
  • Weight percentage of the water-soluble polymer in the aqueous phase is calculated by the amount present in the oil phase for interaction with the oil phase itself and/or oil phase constituents (e.g., the first adduct, the optional second multifunctional crosslinker).
  • the water-soluble polymer may be present in the aqueous phase in amount of about 0.5% to about 15% by weight of the dry weight of the oil phase.
  • the water-soluble polymer is present in the aqueous phase in amount of about 3% to about 12%, or about 5% to about 10% by weight of the dry weight of the oil phase.
  • the aqueous phase further comprises a water-soluble low molecular weight chain extender or crosslinker. The inclusion of the water-soluble low molecular weight chain extender or crosslinker may increase the degree of crosslinking of the random polymerization product.
  • the aqueous phase further comprises a surfactant.
  • the surfactant is a non-ionic surfactant.
  • the non-ionic surfactant preferably has an average HLB (hydrophilic-lipophilic balance) value of Atty. Dkt. No. 130952-0701 about 12 to about 15.
  • Non-ionic surfactants include, but are not limited to, TRITON TM X-114 ((1,1,3,3-tetramethylbutyl)phenyl-polyethylene glycol), SILWET TM L-7604 (siloxane polyalkyleneoxide copolymer), and a combination thereof.
  • Weight percentage of the surfactant in the aqueous phase is calculated by the amount present in the oil phase for interaction with or adsorption on 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.
  • the surfactant is present in the aqueous phase in an amount of about 0.05% to about 2%, or about 0.1% to about 1% by weight based on the dry weight of the oil phase.
  • the aqueous phase further comprises a defoamer or antifoamer.
  • the defoamer is FOAMSTAR ® ST 2410 (star polymer- based defoamer).
  • the polymers described herein and the general method to prepare them offers a great deal of versatility to adjust and fine-tune physical and chemical properties and their antimicrobial properties for a wide range of different surfaces, substrates and applications.
  • variables available for this fine-tuning include, but are not limited to, the structure and amount of the first quaternary ammonium salt, the polyol, the optional chain extender), the water-soluble polymer, the first multifunctional crosslinker (e.g., the first polyisocyanate), the optional second quaternary ammonium salt, the optional second multifunctional crosslinker, and the degree of cross-linking.
  • Non-limiting examples of the device, equipment, apparatus, or accessory include a filter, an air purifier, mask, or other personal protection device (PPD), respirator, etc.
  • Other non-limiting examples include a keyboard, a keypad, a stylus, a mouse, a remote controller, a touch screen, a phone, and a display or any device integrating any of the foregoing components.
  • PPD personal protection device
  • a keyboard, a keypad, a stylus, a mouse, a remote controller, a touch screen, a phone, and a display or any device integrating any of the foregoing components Atty. Dkt. No. 130952-0701 [0270]
  • a personal care aid comprising the coating, coating fluid, or spraying fluid described herein.
  • Non-limiting examples of a personal care aid include facial tissue, hand soap, and a cleansing pad.
  • a method to sanitize a surface comprising, consisting essentially of, or consisting of applying a composition disclosed herein to the surface.
  • a method to reduce (e.g., minimize) antimicrobial growth on a surface comprising, consisting essentially of, or consisting of applying a composition disclosed herein to the surface.
  • the method includes forming a coating solution containing a composition according to any of the embodiments set forth herein.
  • the method further includes directing, via an applicator (e.g., a sprayer), the coating solution to a surface, and providing a coating on the surface through the application of the coating solution to the surface.
  • an applicator e.g., a sprayer
  • the method comprising, consisting essentially of, or consisting of applying a composition disclosed herein to the surface.
  • the applying step comprises, consists essentially of, or consists of spraying or brushing the surface with the composition.
  • the applying step comprises, consists essentially of, or consists of dipping the surface into a coating solution containing a composition according to any of the embodiments set forth herein. In some embodiments of the methods described above, the applying step comprises, consists essentially of, or consists of applying the composition to the surface by an electrostatic process.
  • the antiviral activity was determined by two different methods: (i) the human cell (HuH7) method; and (ii) the quantitative reverse transcription polymerase chain reaction (RT-qPCR) method. Atty. Dkt. No. 130952-0701 (i) Human cell (HuH7) Method [0287] Huh7 is a type of human liver cell line that may be grown in the laboratory for research purposes.
  • hepatocyte-derived carcinoma cell line According to the web site huh7.com, it is "a well differentiated hepatocyte-derived carcinoma cell line, originally taken from a liver tumor in a 57-year-old Japanese male in 1982.”
  • DMEM Dulbecco
  • FBS fetal bovine serum
  • RT-qPCR is used in a variety of applications including pathogen detection, gene expression analysis, RNAi validation, microarray validation, genetic testing, and disease research.
  • the medium (DMEM, high sucrose, pyruvate; ThermoFisher, Catalog number: 11995040) was removed from the refrigerator and conditioned in a water bath at 37 o C for 30 min.
  • Preparation of Virus Fluid The typical virus count of the stock is 5 Lambda (5x10 8 ) per tube. To the virus tube, 1 mL of DMEM medium was added and the tube was mixed homogeneously with a vortex mixer for 5-10 sec to make a virus fluid of 5x10 8 /mL concentration. The virus fluid was further diluted to 5x10 7 /mL with DMEM medium for the antivirus tests.
  • RT-qPCR Procedure for Coatings The coated film was immersed in 99% alcohol for 1 sec. Any excess alcohol was removed from the surface. The film was then air- dried in a new petri dish for 15-20 min. Then 100 ⁇ L of the diluted virus fluid (5x10 6 /mL) was dropped onto the dried film. The petri dish was covered, and the virus allowed to contact the film for desired contact time period. In some of the experiments, the contact time was reduced to as short as 30 sec. The virus fluid from the film was transferred to an Eppendorf Atty. Dkt. No. 130952-0701 tube. The film was then rinsed twice with 50 ⁇ L of 1X PBD and the rinsing fluid was combined into the Eppendorf tube.
  • RT-qPCR Procedure for Aqueous Solutions 100 ⁇ L of the test sample was added to 100 ⁇ L of the diluted virus fluid (5x10 7 /mL) in an Eppendorf tube and the mixture (5x10 6 virus count) was shaken on a shaker for 30 min. DNA was extracted using the Novogene DNA kit following the specified extraction procedure.
  • RT-qPCR Tests Each sample was tested in quadruplicates. The ingredients listed in Table 1 were mixed thoroughly in an Eppendorf tube.
  • TESTING [0298] Qualitative Cell Viability Test for Coatings: The coating was placed in a petri dish and 100 ⁇ L of DMEM medium was dropped on the coating. The petri dish was Atty. Dkt. No. 130952-0701 then covered for 30 min. The medium on the film was then transferred to a cell plate containing 8x10 4 cells in 500 ⁇ L of medium in each partition. The film was rinsed twice with 50 ⁇ L of DMEM medium and the rising fluid was combined with previous test fluid in the same location in the plate. A total of 200 ⁇ L of the test fluid was added to the 500 ⁇ L cell/medium.
  • the cell plate was incubated at a 37 o C/95%RH CO 2 incubator for 48-96 hours, after which the cell growth and morphology were observed under visible microscope. Dead cells floated or were suspended in the medium, while live cells remained fixed to the bottom of the plate. This test was for the assessment of the contact cytotoxicity of the polymer film. In cases where this test indicates some degree of cytotoxicity, the actual mechanism for the cell death is not given although cell death due to chemicals extracting from the coating are one possibility. [0299] Qualitative Cell Viability Test for Polymer Solution or Dispersion: 100 ⁇ L of the polymer solution or dispersion and 100 ⁇ L of DMEM medium were added to an Eppendorf and mixed thoroughly with a shaker for 30 min.
  • test mixture was added in a cell plate containing 8x10 4 cells in 500 ⁇ L of medium in each partition. The cell plate was then incubated at a 37 o C/95%RH CO 2 incubator for 48-96 hours. Finally, the cell morphology and the fluorescence were recorded under UV microscope.
  • EXPERIMENTAL RESULTS – ANTIVIRAL ACTIVITY AND TOXICITY [0302] The coating from Example 1 was tested against a range of bacteria, viruses and fungi. Select data are shown in Tables 2 and 3 below. Ta M icrobe Antibacterial Efficiency Atty. Dkt. No. 130952-0701 ISO 22196:2011 ASTM E2149 S a G Table 3.
  • the quaternary PEI polymers shown below did not form colorless, transparent, durable water and alcohol resistant coatings and were only moderately antivirally active.
  • the two latex quaternary polymers shown below exhibited antiviral activity but were toxic to HuH7 cells.
  • Atty. Dkt. No. 130952-0701 [0304]
  • Mundex-W and Mundex-L-K are two “self- disinfecting polymer emulsions” for treating surfaces. Both were found to be very weakly antiviral against adenovirus. Not unexpectedly, the water-based Mundex-W did not give a durable water or alcohol resistant surface coating.
  • the solvent-based Mundex-L-K did give a more hydrophobic coating but its water or alcohol resistance was only marginal. Moreover, both of them were found toxic to HuH7 cells.
  • Atty. Dkt. No. 130952-0701 The LIVINGUARD® face mask includes an antiviral component. This mask exhibited only a marginal antiviral efficiency of ⁇ 44% after one minute contact time and ⁇ 72% after 20 minutes contact time. These efficiencies were significantly reduced after the mask was pre-conditioned at 40 o C 85% RH for 96 hours.
  • the antimicrobial polymers of the present technology produce surface coatings that displayed the following properties: (i) highly antimicrobial activity against viruses, bacteria, and fungus; (ii) fast acting; (iii) long lasting; (iv) non-toxic and nonallergenic; (v) no materials leaching out of the coating; (vi) colorless and transparent as a surface coating; (vii) easy application to a wide range of surfaces and materials; (viii) durable surface coating resistant to water and common solvents; and (ix) easy and cost effective to produce. Accordingly, these antimicrobial polymers represent an improved class of antimicrobial polymers. REFERENCES: 1 Ellingson, K.D., et al. (2020).
  • 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). Atty. Dkt. No. 130952-0701 11 LABORATORY METHODS IN ENZYMOLOGY: DNA, (2013). Jon Lorsch (ed.) Elsevier (ISBN 0124199542). 12 CURRENT PROTOCOLS IN MOLECULAR BIOLOGY (CPMB), (2014). Frederick M.
  • 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 S.L. and Guan, J. (eds.), Elsevier Ltd. 22 Park, D., et al., (2013).

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Abstract

L'invention concerne des polymères d'ammonium quaternaire et des compositions ayant des propriétés antimicrobiennes à large spectre qui produisent des revêtements de surface durables, incolores, non toxiques et non allergéniques à action rapide qui sont résistants à l'eau et à des solvants communs. Les revêtements de surface sont faciles et économiques à produire à partir de matériaux facilement disponibles à l'aide d'une synthèse polyvalente permettant une large gamme de variations chimiques. De tels revêtements sont facilement appliqués à une large gamme de surfaces et de matériaux, et aucun matériau ne s'échappe des revêtements.
EP23786335.2A 2022-09-28 2023-09-27 Compositions de revêtement antimicrobiennes Pending EP4593601A1 (fr)

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US12617890B2 (en) 2020-02-07 2026-05-05 Lanxess Solutions Australia Pty. Ltd. Polyurethane multi-part kit system

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US4939289A (en) * 1985-08-15 1990-07-03 Allied-Signal Inc. Fiber surface modifiers
US5783502A (en) 1995-06-07 1998-07-21 Bsi Corporation Virus inactivating coatings
WO2007024973A1 (fr) * 2005-08-22 2007-03-01 Quick-Med Technologies, Inc. Desinfectant a activite durable a base de polymeres et de copolymeres d'ammonium quaternaire solubles dans l'alcool
WO2008035246A2 (fr) * 2006-07-28 2008-03-27 Novagali Pharma Sa Compositions contenant des composés ammonium quaternaire
WO2016148649A1 (fr) * 2015-03-16 2016-09-22 Agency For Science, Technology And Research Halogénures d'ammonium quaternaire fonctionnalisés et leur utilisation

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US12617890B2 (en) 2020-02-07 2026-05-05 Lanxess Solutions Australia Pty. Ltd. Polyurethane multi-part kit system

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