IP Library Granted Patent US 10,721,907
Granted Patent B2
US 10,721,907 · App. 16/043,469 · Granted Jul 28, 2020

Antimicrobial compositions and methods with novel polymeric binding system

Inventors: Zhengbing Cao (Bothell, WA); Xinbo Sun (Bothell, WA); Simon Johnston (Bellevue, WA); Jeffrey F. Williams (Langley, WA)
Assignee: OXISCIENCE, LLC
A01K1/0154A01K1/0152A01K1/0155A01N33/12A01N43/50A01N43/66A01N59/00A61K31/00A61K31/4166A61K31/53A61L15/22A61L15/28A61L15/46A61L2300/204A61L2300/404A61L2300/606
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Quick Facts
Patent No.
US 10,721,907
App. No.
16/043,469
Granted
Jul 28, 2020
Kind
B2
Abstract

The present invention includes multifunctional compositions, methods and binding systems to provide disinfecting and deodorizing coatings for hard and soft surfaces, inorganic and organic solid surfaces and particulate media and other related substrates, including human and animal skin and skin lesions; to provide neutralizing functions for malodors generated by both human, animal and industrial fluids and solid wastes; and to provide neutralizing and degrading functions for nuisance and noxious chemicals. The present invention provides compositions and methods for producing disinfecting, oxidizing and enzyme-inhibiting fluids enabling preparation of durable, stable biocidal and deodorizing coatings and media which can be widely used for biological agent control, prevention and elimination of odors, and degradation of noxious agents susceptible to chemical oxidation, and which take forms that are inoffensive to users and offer high convenience.

Claims (19)

1. A method for preparing an antimicrobial and/or deodorizing and/or enzyme inactivating material by applying a water-based disinfecting and deodorizing fluid to a substrate of said material and allowing the fluid to dry on said substrate to create the antimicrobial and/or deodorizing and/or enzyme inactivating material, wherein the water-based disinfecting and deodorizing fluid is comprised of (a) at least N-halamine, wherein the N-halamine is selected from the group consisting of N-chloro-N-sodiomethylbenzenesulfonamidate trihydrate, N,N-dichloro-4-methylbenzenesulfonamide, N-bromo-N-sodio-4-nitrobenzenesulfonamidate, N,N-dichlorobenzenesulfonamide, N-chloro-N-sodiobenzenesulfonamidate, mono-chlorosulfamate, dichlorosulfamate, N-chloroimidodisulfonates, sodium N-chloro-N-arylsulfamates, 2,4,6,8-tetrachloro-2,4,6,8-tetrazobicyclooctane-3,7-dione, sodium trichloroimidometaphosphamate, N-halosulfinylamines, N-halo-N-sodioamidates, chloroisocyanurates, N-halocarbamidates, N-halosulfonamidates, N-chloro-imidodisulfonate, N,N-dichloromethylamine, 2-chloro-1,3,5-triazine-2,4,6-triamine, 2,4-dichloro-1,3,5-triazine-2,4,6-triamine, 2,4,6-trichloro-1,3,5-triazine-2,4,6-triamine, 1-chloro-5,5-dimethylhydantoin, 1-bromo-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin 1-chloro-3-bromo-5,5-dimethylhydantoin, 1,3-dichloro-5,5-dimethylhydantoin, 1-chloro-4,4,5,5-tetramethylimidazolidin-2-one, 1,3-dichloro-4,4,5,5-tetramethylimidazolidin-2-one, 1-chloro-2,2,5,5-tetramethylimidazolidin-4-one, 1,3-dichloro-2,2,5,5-tetramethylimidazolidin-4-one, 1,3-dichloro-s-triazine-2,4,6-trione, trichloroisocyanuric acid, potassium dichloroisocyanurate, sodium dichloroisocyanurate, potassium dibromoisocyanurate, sodium dibromoisocyanurate, mono to hexachloromelamine, mono to hexabromomelamine, 3-chloro-4,4-dimethyl-2-oxazolidinone, N-chlorosuccinimide, 1-chloropyrrolidine-2,5-dione, 1,3-dichlorotetrahydroquinazoline-2,4-dione, 1,4-dichloro-2,2,5,5-tetrasubstituted-piperazine-3,6-diones, N-chloro-2,2,6,6-tetramethylpiperidine, N-chloro-4-amino-2,2,6,6-tetramethylpiperidine, polymer-bound N-chloro-N-sodiobenzenesulfonamidates, chlorinated polyacrylamide, brominated polyacrylamide, chlorinated poly(methacrylamide), brominated poly(methacrylamide), poly(N-chloro-2,2,6,6-tetramethyl-4-piperidinyl acrylate), poly(N-chloro-hydantoin-methyl-p-styrene) emulsion, 1-chloro-3-bromoalkyltrimethylammonium-4,4,5,5-tetramethyl imidazolidin-2-one, 1-bromo-3-bromoalkyltrimethylammonium-4,4,5,5-tetramethyl imidazolidin-2-one, 1-chloro-3-bromoalkyltrimethylammonium-2,2,5,5-tetramethyl imidazolidin-4-one, 1-bromo-3-bromoalkyltrimethylammonium-2,2,5,5-tetramethyl imidazolidin-4-one, 2-chloro-4-bromoalkyltrimethylammonium-1,3,5-triazine-2,4,6-triamine, 2-bromo-4-bromoalkyltrimethylammonium-1,3,5-triazine-2,4,6-triamine, 1-chloro-3-bromoalkyltrimethylammonium-5,5-dimethylhydantoin, and 1 bromo-3-bromoalkyltrimethylammonium-5,5-dimethylhydantoin; and (b) at least one halogen stabilizing compound or at least one polymeric binder/stabilizing agent, wherein the halogen stabilizing compound is selected from the group consisting of hydroquinone, 2,2,5,5-tetramethylimidazolidine-4-one, (2,2,6,6-tetramethylpiperidin-1-yl)oxy, 2,2,6,6-tetramethyl-piperidine-1,4-diol, 2,2,6,6-tetramethyl-4-piperidinol, 4-amino-2,2,6,6-tetramethylpiperidine, 2,2,6,6-tetramethylpiperidine, 2,2,6,6-tetramethyl-4-piperidyl methacrylate, 2,2,6,6-tetramethyl-4-piperidone, (2,2,6,6-tetramethylpiperidin-4-yl) benzoate, 1,1′-ethylenebis(3,3,5,5-tetramethylpiperazinone), 4-acetamido-2,2,6,6-tetramethylpiperidine, bis(2,2,6,6-tetramethyl-4-piperidyl) succinate, bis(2,2,6,6-tetramethylpiperidin-4-yl) butanedioate, bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine, and wherein the polymeric binder/stabilizing agent is selected from the group consisting of cellulose, carboxylic cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, starch, guar gum, gelatin, vinyl resin emulsion, acrylic resin emulsion, polyacrylamide, poly(methacrylamide), polyacrylic acid, polyethyleneimine, poly(vinyl alcohol), poly(vinylpyrrolidinone), poly(ethylene glycol), poly(ethylene oxide), poly(N-isopropylacrylamide), poly(2-oxazoline), poly(allylamine hydrochloride), poly(styrenesulfonate), and poly(diallyldimethylammonium chloride).

2. The method as specified in claim 1 wherein the water-based disinfecting and deodorizing fluid includes at least one of both the halogen stabilizing compounds and at least one of the the polymeric binder/stabilizing agents.

3. The method as specified in claim 1 wherein the material is a woven textile material or a nonwoven textile material.

4. The method as specified in claim 2 wherein the material is a woven textile material or a nonwoven textile material.

5. The method as specified in claim 1 wherein the material is solid material.

6. The method as specified in claim 2 wherein the material is solid material.

7. The method as specified in claim 1 wherein the material is a particulate material, wherein the particulate material is inorganic or organic, wherein the particulate material is porous or non-porous, and wherein the particulate material is natural or synthetic.

8. The method as specified in claim 2 wherein the material is a particulate material, wherein the particulate material is inorganic or organic, wherein the particulate material is porous or non-porous, and wherein the particulate material is natural or synthetic.

9. The method as specified in claim 1 wherein the material is a porous material.

10. The method as specified in claim 9 wherein the material is a sponge or foam or granular medium.

11. The method as specified in claim 2 wherein the material is a porous material.

12. The method as specified in claim 11 wherein the material is a sponge or foam or granular medium.

13. A method for disinfecting and/or deodorizing an area of skin on a human or an animal which comprises applying a water-based disinfecting and deodorizing fluid to the area of skin on the human or the animal, wherein the water-based disinfecting and deodorizing fluid is comprised of (a) at least one N-halamine, wherein the N-halamine is selected from the group consisting of N-chloro-N-sodiomethylbenzenesulfonamidate trihydrate, N,N-dichloro-4-methylbenzenesulfonamide, N-bromo-N-sodio-4-nitrobenzenesulfonamidate, N,N-dichlorobenzenesulfonamide, N-chloro-N-sodiobenzenesulfonamidate, mono-chlorosulfamate, dichlorosulfamate, N-chloroimidodisulfonates, sodium N-chloro-N-arylsulfamates, 2,4,6,8-tetrachloro-2,4,6,8-tetrazobicyclooctane-3,7-dione, sodium trichloroimidometaphosphamate, N-halosulfinylamines, N-halo-N-sodioamidates, chloroisocyanurates, N-halocarbamidates, N-halosulfonamidates, N-chloro-imidodisulfonate, N,N-dichloromethylamine, 2-chloro-1,3,5-triazine-2,4,6-triamine, 2,4-dichloro-1,3,5-triazine-2,4,6-triamine, 2,4,6-trichloro-1,3,5-triazine-2,4,6-triamine, 1-chloro-5,5-dimethylhydantoin, 1-bromo-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin 1-chloro-3-bromo-5,5-dimethylhydantoin, 1,3-dichloro-5,5-dimethylhydantoin, 1-chloro-4,4,5,5-tetramethylimidazolidin-2-one, 1,3-dichloro-4,4,5,5-tetramethylimidazolidin-2-one, 1-chloro-2,2,5,5-tetramethylimidazolidin-4-one, 1,3-dichloro-2,2,5,5-tetramethylimidazolidin-4-one, 1,3-dichloro-s-triazine-2,4,6-trione, trichloroisocyanuric acid, potassium dichloroisocyanurate, sodium dichloroisocyanurate, potassium dibromoisocyanurate, sodium dibromoisocyanurate, mono to hexachloromelamine, mono to hexabromomelamine, 3-chloro-4,4-dimethyl-2-oxazolidinone, N-chlorosuccinimide, 1-chloropyrrolidine-2,5-dione, 1,3-dichlorotetrahydroquinazoline-2,4-dione, 1,4-dichloro-2,2,5,5-tetrasubstituted-piperazine-3,6-diones, N-chloro-2,2,6,6-tetramethylpiperidine, N-chloro-4-amino-2,2,6,6-tetramethylpiperidine, polymer-bound N-chloro-N-sodiobenzenesulfonamidates, chlorinated polyacrylamide, brominated polyacrylamide, chlorinated poly(methacrylamide), brominated poly(methacrylamide), poly(N-chloro-2,2,6,6-tetramethyl-4-piperidinyl acrylate), poly(N-chloro-hydantoin-methyl-p-styrene) emulsion, 1-chloro-3-bromoalkyltrimethylammonium-4,4,5,5-tetramethyl imidazolidin-2-one, 1-bromo-3-bromoalkyltrimethylammonium-4,4,5,5-tetramethyl imidazolidin-2-one, 1-chloro-3-bromoalkyltrimethylammonium-2,2,5,5-tetramethyl imidazolidin-4-one, 1-bromo-3-bromoalkyltrimethylammonium-2,2,5,5-tetramethyl imidazolidin-4-one, 2-chloro-4-bromoalkyltrimethylammonium-1,3,5-triazine-2,4,6-triamine, 2-bromo-4-bromoalkyltrimethylammonium-1,3,5-triazine-2,4,6-triamine, 1-chloro-3-bromoalkyltrimethylammonium-5,5-dimethylhydantoin, and 1 bromo-3-bromoalkyltrimethylammonium-5,5-dimethylhydantoin; and (b) at least one halogen stabilizing compound or at least one polymeric binder/stabilizing agent, wherein the halogen stabilizing compound is selected from the group consisting of hydroquinone, 2,2,5,5-tetramethylimidazolidine-4-one, (2,2,6,6-tetramethylpiperidin-1-yl)oxy, 2,2,6,6-tetramethyl-piperidine-1,4-diol, 2,2,6,6-tetramethyl-4-piperidinol, 4-amino-2,2,6,6-tetramethylpiperidine, 2,2,6,6-tetramethylpiperidine, 2,2,6,6-tetramethyl-4-piperidyl methacrylate, 2,2,6,6-tetramethyl-4-piperidone, (2,2,6,6-tetramethylpiperidin-4-yl) benzoate, 1,1′-ethylenebis(3,3,5,5-tetramethylpiperazinone), 4-acetamido-2,2,6,6-tetramethylpiperidine, bis(2,2,6,6-tetramethyl-4-piperidyl) succinate, bis(2,2,6,6-tetramethylpiperidin-4-yl) butanedioate, bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine, and wherein the polymeric binder/stabilizing agent is selected from the group consisting of cellulose, carboxylic cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, starch, guar gum, gelatin, vinyl resin emulsion, acrylic resin emulsion, polyacrylamide, poly(methacrylamide), polyacrylic acid, polyethyleneimine, poly(vinyl alcohol), poly(vinylpyrrolidinone), poly(ethylene glycol), poly(ethylene oxide), poly(N-isopropylacrylamide), poly(2-oxazoline), poly(allylamine hydrochloride), poly(styrenesulfonate), and poly(diallyldimethylammonium chloride).

14. The method as specified in claim 13 wherein the water-based disinfecting and deodorizing fluid includes at least one of the halogen stabilizing compounds and at least one of the one water soluble/dispersible polymeric binder/stabilizing agents.

15. The method for disinfecting and/or deodorizing the surface of equipment for use in food processing, agricultural, or industrial processes which comprises applying a water-based disinfecting and deodorizing fluid to the surface of said equipment, wherein the water-based disinfecting and deodorizing fluid is comprised of (a) at least one N-halamine, wherein the N-halamine is selected from the group consisting of N-chloro-N-sodiomethylbenzenesulfonamidate trihydrate, N,N-dichloro-4-methylbenzenesulfonamide, N-bromo-N-sodio-4-nitrobenzenesulfonamidate, N,N-dichlorobenzenesulfonamide, N-chloro-N-sodiobenzenesulfonamidate, mono-chlorosulfamate, dichlorosulfamate, N-chloroimidodisulfonates, sodium N-chloro-N-arylsulfamates, 2,4,6,8-tetrachloro-2,4,6,8-tetrazobicyclooctane-3,7-dione, sodium trichloroimidometaphosphamate, N-halosulfinylamines, N-halo-N-sodioamidates, chloroisocyanurates, N-halocarbamidates, N-halosulfonamidates, N-chloro-imidodisulfonate, N,N-dichloromethylamine, 2-chloro-1,3,5-triazine-2,4,6-triamine, 2,4-dichloro-1,3,5-triazine-2,4,6-triamine, 2,4,6-trichloro-1,3,5-triazine-2,4,6-triamine, 1-chloro-5,5-dimethylhydantoin, 1-bromo-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin 1-chloro-3-bromo-5,5-dimethylhydantoin, 1,3-dichloro-5,5-dimethylhydantoin, 1-chloro-4,4,5,5-tetramethylimidazolidin-2-one, 1,3-dichloro-4,4,5,5-tetramethylimidazolidin-2-one, 1-chloro-2,2,5,5-tetramethylimidazolidin-4-one, 1,3-dichloro-2,2,5,5-tetramethylimidazolidin-4-one, 1,3-dichloro-s-triazine-2,4,6-trione, trichloroisocyanuric acid, potassium dichloroisocyanurate, sodium dichloroisocyanurate, potassium dibromoisocyanurate, sodium dibromoisocyanurate, mono to hexachloromelamine, mono to hexabromomelamine, 3-chloro-4,4-dimethyl-2-oxazolidinone, N-chlorosuccinimide, 1-chloropyrrolidine-2,5-dione, 1,3-dichlorotetrahydroquinazoline-2,4-dione, 1,4-dichloro-2,2,5,5-tetrasubstituted-piperazine-3,6-diones, N-chloro-2,2,6,6-tetramethylpiperidine, N-chloro-4-amino-2,2,6,6-tetramethylpiperidine, polymer-bound N-chloro-N-sodiobenzenesulfonamidates, chlorinated polyacrylamide, brominated polyacrylamide, chlorinated poly(methacrylamide), brominated poly(methacrylamide), poly(N-chloro-2,2,6,6-tetramethyl-4-piperidinyl acrylate), poly(N-chloro-hydantoin-methyl-p-styrene) emulsion, 1-chloro-3-bromoalkyltrimethylammonium-4,4,5,5-tetramethyl imidazolidin-2-one, 1-bromo-3-bromoalkyltrimethylammonium-4,4,5,5-tetramethyl imidazolidin-2-one, 1-chloro-3-bromoalkyltrimethylammonium-2,2,5,5-tetramethyl imidazolidin-4-one, 1-bromo-3-bromoalkyltrimethylammonium-2,2,5,5-tetramethyl imidazolidin-4-one, 2-chloro-4-bromoalkyltrimethylammonium-1,3,5-triazine-2,4,6-triamine, 2-bromo-4-bromoalkyltrimethylammonium-1,3,5-triazine-2,4,6-triamine, 1-chloro-3-bromoalkyltrimethylammonium-5,5-dimethylhydantoin, and 1 bromo-3-bromoalkyltrimethylammonium-5,5-dimethylhydantoin; and (b) at least halogen stabilizing compound or at least one polymeric binder/stabilizing agent, wherein the halogen stabilizing compound is selected from the group consisting of hydroquinone, 2,2,5,5-tetramethylimidazolidine-4-one, (2,2,6,6-tetramethylpiperidin-1-yl)oxy, 2,2,6,6-tetramethyl-piperidine-1,4-diol, 2,2,6,6-tetramethyl-4-piperidinol, 4-amino-2,2,6,6-tetramethylpiperidine, 2,2,6,6-tetramethylpiperidine, 2,2,6,6-tetramethyl-4-piperidyl methacrylate, 2,2,6,6-tetramethyl-4-piperidone, (2,2,6,6-tetramethylpiperidin-4-yl) benzoate, 1,1′-ethylenebis(3,3,5,5-tetramethylpiperazinone), 4-acetamido-2,2,6,6-tetramethylpiperidine, bis(2,2,6,6-tetramethyl-4-piperidyl) succinate, bis(2,2,6,6-tetramethylpiperidin-4-yl) butanedioate, and bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine, and wherein the polymeric binder/stabilizing agent is selected from the group consisting of cellulose, carboxylic cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, starch, guar gum, gelatin, vinyl resin emulsion, acrylic resin emulsion, polyacrylamide, poly(methacrylamide), polyacrylic acid, polyethyleneimine, poly(vinyl alcohol), poly(vinylpyrrolidinone), poly(ethylene glycol), poly(ethylene oxide), poly(N-isopropylacrylamide), poly(2-oxazoline), poly(allylamine hydrochloride), poly(styrenesulfonate), and poly(diallyldimethylammonium chloride).

16. The method as specified in claim 15 wherein the water-based disinfecting and deodorizing fluid includes at least one of the halogen stabilizing compounds and at least one of the polymeric binder/stabilizing agents.

17. The method as specified in claim 1 wherein the N-halamine is present in the water-based disinfecting and deodorizing fluid at a level which is within the range of 0.01 weight percent to 2 weight percent, based upon the total weight of the water-based disinfecting and deodorizing fluid.

18. The method as specified in claim 1 wherein the N-halamine is present in the water-based disinfecting and deodorizing fluid at a level which is within the range of 0.1 weight percent to 1 weight percent, based upon the total weight of the water-based disinfecting and deodorizing fluid.

19. The method as specified in claim 1 wherein the N-halamine is present in the water-based disinfecting and deodorizing fluid at a level which is within the range of 0.2 weight percent to 0.5 weight percent, based upon the total weight of the water-based disinfecting and deodorizing fluid.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 31, 2024
From: OXISCIENCE LLC
To: OXISCIENCE WA, LLC
Reel/Frame 069705/0300 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 17, 2020
From: CAO, ZHENGBING; JOHNSTON, SIMON; WILLIAMS, JEFFREY
To: OXISCIENCE, LLC
Reel/Frame 052966/0883 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 4, 2020
From: OXISCIENCE, LLC
To: CLINTON MEADE, LENDER RESPRESENTATIVE
Reel/Frame 053452/0507 →
Cited By (1)
US 12,516,199