Antibacterial surfactant/microgel formulations, methods of making and methods of using the same

Patent metadata

Field	Value
Publication number	US-10010078-B2
Application number	US-201615382968-A
Country	US
Kind code	B2
Filing date	Dec 19, 2016
Priority date	Jun 9, 2012
Publication date	Jul 3, 2018
Grant date	Jul 3, 2018

Abstract

Formulations having, as active agents, at least one quaternized polymeric microgel and at least one nonionic surfactant, methods of making, and methods of using are described.

First claim

What is claimed is:

1. An antimicrobial formulation comprising:
a nonionic surfactant providing colloidal stability to the formulation, wherein the nonionic surfactant comprises a hydrophilic polyethylene oxide chain and is selected from the group consisting of a polyoxypropylene glycol alkyl ether, a glycol octylphenol ether, an ethoxylated alkylphenol, a glucoside alkyl ether, and a polyoxyethylene glycol alkylphenol ether; and
a quaternized polymeric chitosan microgel dispersed in a solution of the nonionic surfactant;
wherein the quaternized polymeric chitosan microgel comprises particles having a size distribution in the range of about 10 nm to about 1000 nm; and
wherein the antimicrobial formulation is essentially free of cationic surfactants.

2. The antimicrobial formulation of claim 1 , wherein the quaternized polymeric chitosan microgel comprises at least one quaternized chitosan selected from the group consisting of N-[(2-hydroxy-3-trimethylammonium) propyl] chitosan chloride; hydroxypropyl chitosan; N,N,N-trimethyl chitosan; N,N,N-dimethyl chitosan propyl-(QuatPropyl); N,N,N-dimethyl chitosan butyl-(QuatButyl); N,N,N-dimethyl chitosan hexyl (QuatHexyl); N-(4-N,N-dimethylaminocinnamyl) chitosan chloride; N,N-octylchitosan; N-benzylchitosan; N-(4-methylbenzylchitosan); N-(4-hydroxybenzyl) chitosan; N-(2-methoxybenzyl) chitosan; N-(4-methoxybenzyl) chitosan; N-(3,4-dimethoxybenzyl) chitosan; N-(4-fluorobenzyl) chitosan; N-(4-chlorobenzyl) chitosan; N-(3-bromobenzyl) chitosan; N-(4-bromobenzyl) chitosan; N-(4-trifluorobenzyl) chitosan; N-(4-nitrobenzyl) chitosan; N-(4-carboxybenzyl) chitosan; N-(4-pyridinylmethyl) chitosan; N-(2-thiophenylmethyl) chitosan; and combinations thereof.

3. The antimicrobial formulation of claim 1 , wherein the total concentration of the quaternized polymeric chitosan microgel ranges from about 0.01% to about 0.5%, by weight.

4. The antimicrobial formulation of claim 1 , wherein the total concentration of the quaternized polymeric chitosan microgel is about 0.1%, by weight.

5. The antimicrobial formulation of claim 1 , wherein the nonionic surfactant is present at a concentration, based on the total weight of the formulation, of about 250 mmol/kg or less, about 100 mmol/kg or less, about 25 mmol/kg or less, about 15 mmol/kg or less, or about 5 mmol/kg or less.

6. The antimicrobial formulation of claim 1 , wherein the quaternized polymeric chitosan microgel comprises N-[(2-hydroxy-3-trimethylammonium) propyl] chitosan chloride.

7. The antimicrobial formulation of claim 6 , wherein the nonionic surfactant is present at a concentration ranging from about 0.05% to about 1%, by weight per volume of the formulation in water; and the N-[(2-hydroxy-3-trimethylammonium) propyl] chitosan chloride is present at a concentration ranging from about 0.01% to about 3%, by weight per volume of the formulation in water.

8. The antimicrobial formulation of claim 1 , wherein the quaternized polymeric chitosan microgel is prepared by ionic cross-linking of quaternized chitosan with sodium tripolyphosphate.

9. The antimicrobial formulation of claim 1 , further comprising at least one aqueous carrier material.

10. The antimicrobial formulation of claim 1 , further comprising an anionic surfactant present at a concentration such that amine groups on the quaternized polymeric microgel are not neutralized.

11. The antimicrobial formulation of claim 10 , wherein the anionic and nonionic surfactants are present in a concentration ratio of from about 30:70 to about 40:60, respectively.

12. The antimicrobial formulation of claim 11 , wherein the anionic and nonionic surfactants are present in a surfactant admixture and have a concentration ratio of about 40:60, respectively, the quaternized polymeric microgel is dispersed in the surfactant admixture, and the surfactant admixture has a concentration of about 3 mmol/kg or less, based on the weight of the formulation.

13. The antimicrobial formulation of claim 10 , wherein the anionic surfactant is present at a concentration, based on the total weight of the formulation, of about 2 mmol/kg or less, about 1 mmol/kg or less, or about 0.5 mmol/kg or less.

14. The antimicrobial formulation of claim 10 , wherein the anionic surfactant comprises one or more alkali metal C 8-18 alkyl sulfates.

15. The antimicrobial formulation of claim 14 , wherein the alkali metal C 8-18 alkyl sulfates are selected from the group consisting of sodium lauryl sulfate, sodium laureth sulfates, alkyl ether sulfates, alkyl benzene sulfonates, fatty acids, and fatty acid salts.

16. The antimicrobial formulation of claim 15 , wherein the anionic surfactant is sodium dodecyl sulfate.

17. The antimicrobial formulation of claim 1 , wherein the antimicrobial formulation is in the form of a tablet, powder, gel, capsule, liquid, coating, film, foam, sponge, woven material, non-woven material, knitted material, textile material, porous material, or solid material.

18. An article comprising a porous or solid material comprising, or at least partially coated with, the antimicrobial formulation of claim 1 .

19. An antimicrobial formulation comprising:
a nonionic surfactant present at a concentration in the range of from about 0.05% to about 3%, by weight of the formulation, wherein the nonionic surfactant comprises a hydrophilic polyethylene oxide chain and is selected from the group consisting of a polyoxypropylene glycol alkyl ether, a glycol octylphenol ether, an ethoxylated alkylphenol, a glucoside alkyl ether, and a polyoxyethylene glycol alkylphenol ether; and,
a quaternized polymeric chitosan microgel dispersed in a solution of the nonionic surfactant and present at a concentration ranging from about 0.01% to about 0.15%, by weight of the formulation.

20. The antimicrobial formulation of claim 19 , wherein the quaternized polymeric chitosan microgel comprises N-[(2-hydroxy-3-trimethylammonium) propyl] chitosan chloride.

Assignees

• Univ Toledo

Inventors

• Lapitsky Yakov
• Seo Youngwoo
• Richardson Kristopher

Classifications

• A01N25/04

  Dispersions, {emulsions, suspoemulsions, suspension concentrates} or gels (foams A01N25/16) · CPC title

• A01N25/30 Primary

  characterised by the surfactants · CPC title

• A01N41/02

  containing a sulfur-to-oxygen double bond · CPC title

• A01N43/16 Primary

  with oxygen as the ring hetero atom · CPC title

• C08B37/003

  Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof · CPC title