IP Library Granted Patent US 9,560,849
Granted Patent B2
US 9,560,849 · App. 14/406,618 · Granted Feb 7, 2017

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

Inventors: Yakov Lapitsky (Toledo, OH); Youngwoo Seo (Ottawa Hills, OH); Kristopher Richardson (Warren, OH)
Assignee: THE UNIVERSITY OF TOLEDO
A01N43/16A01N25/04A01N25/22A01N25/30A01N31/14A01N41/02C08B37/003
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Quick Facts
Patent No.
US 9,560,849
App. No.
14/406,618
Granted
Feb 7, 2017
Kind
B2
Abstract

In a first broad aspect, described herein is an antimicrobial formulation comprised of: at least one nonionic surfactant capable of providing colloidal stability to the formulation, and at least one quaternized polymeric microgel capable of being dispersed in the nonionic surfactant. The quaternized polymeric microgel is comprised of one or more of: chitosan oligomers or chitosan polymers. Further, the antimicrobial formulation is essentially free of cationic surfactants.

Claims (20)

1. An antimicrobial formulation comprising a nonionic surfactant providing colloidal stability to the formulation and a quaternized polymeric chitosan microgel dispersed in a nonionic surfactant solution, and wherein (a) the nonionic surfactant comprises t-octylphenoxypolyethoxyethanol, (b) the antimicrobial formulation is essentially free of cationic surfactants; and (c) the quaternized polymeric chitosan microgel comprises particles having a size distribution in the range of about 10 nm to about 1000 nm.

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; hydroxyalkyl chitosans, including hydroxypropyl chitosan; N,N,N-trimethyl chitosan; N,N,N-dimethyl chitosan propyl; N,N,N-dimethyl chitosan butyl; N,N,N-dimethyl chitosan hexyl; 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; and N-(2-thiophenylmethyl) chitosan.

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 nonionic surfactant further comprises polyoxypropylene glycol alkyl ethers; glycol octylphenol ethers; ethoxylated alkylphenols, including ethoxylated octylphenol; glucoside alkyl ethers; polyoxyethylene glycol alkylphenol ethers; or combination thereof.

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

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

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

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

11. An antimicrobial formulation comprising (a) a nonionic surfactant providing colloidal stability to the formulation and comprising t-octylphenoxypolyethoxyethanol; (b) a quaternized polymeric chitosan microgel dispersed in the nonionic surfactant solution and comprising at least one chitosan oligomer or chitosan polymer; and (c) an anionic surfactant present at a concentration such that amine groups on the quaternized polymeric microgel are not neutralized; and wherein (d) the antimicrobial formulation is essentially free of cationic surfactants.

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

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

15. The antimicrobial formulation of claim 11 , wherein the anionic surfactant comprises one or more alkali metal C 8-18 alkyl sulfates.

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

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

18. The antimicrobial formulation of claim 1 , wherein the 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.

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

20. An article comprising a porous or solid material at least partially comprised of the antimicrobial formulation of claim 1 .

Assignments (2)
CONFIRMATORY LICENSE Recorded Mar 28, 2016
From: UNIVERSITY OF TOLEDO
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 038264/0259 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 5, 2015
From: LAPITSKY, YAKOV; SEO, YOUNGWOO; RICHARDSON, KRISTOPHER
To: THE UNIVERSITY OF TOLEDO
Reel/Frame 034637/0013 →
Continuity (2)
Provisional Application 61657787 · Jun 9, 2012
Related Publication 20150150255A1 · Jun 4, 2015