Antimicrobial solution

Patent metadata

Field	Value
Publication number	US-10633551-B2
Application number	US-201815900338-A
Country	US
Kind code	B2
Filing date	Feb 20, 2018
Priority date	Feb 21, 2017
Publication date	Apr 28, 2020
Grant date	Apr 28, 2020

Abstract

A solution including an antimicrobial polymer in a polar solvent and a method of producing the solution. The polymer has the structure of Formula (I). The antimicrobial solution may be coated onto a substrate and cured to provide an antimicrobial substrate in which the polymer is covalently bonded to the substrate so that it cannot leach from the substrate.

First claim

We claim:

1. A solution including an antimicrobial polymer having the structure of Formula (I):

wherein R 1 is a C 2 -C 7 alkyl;

R 2 is a C 8 -C 15 alkyl;
R 5a is O − or OH and R 5b is OR 6 , or R 5b is O − or OH and R 5a is OR 6 ;
R 3 , R 4 and R 6 are each independently a C 1 -C 4 alkyl;
Hal − is a halide anion selected from the group consisting of bromide (Br − ), chloride (Cl − ) and iodide (I − );
f, i, j, k and l are each independently an integer from 1 to 100;
g is an integer from 0 to 100;
the ratio of j:l is from about 1:1 to 19:1;
0.1<j/(g+j+l)<1.0; in a polar solvent and
wherein n is an integer from about 20 to about 6000.

2. The solution as claimed in claim 1 wherein the ratio of j:l is from about 4:1 to 9:1.

3. The solution as claimed in claim 1 , wherein f, i and k are each independently an integer from 1 to 4.

4. The solution as claimed in claim 1 , wherein R 1 is a C 2 -C 3 alkyl.

5. The solution as claimed in claim 1 , wherein R 2 is a C 9 -C 12 alkyl.

6. The solution as claimed in claim 1 , wherein R 3 and R 4 are methyl groups.

7. The solution as claimed in claim 1 , wherein Hal − is bromide (Br − ).

8. A method of producing a solution including an antimicrobial polymer having the structure of Formula (I):

wherein R 1 is a C 2 -C 7 alkyl;
R 2 is a C 8 -C 15 alkyl;
R 5a is O − or OH and R 5b is OR 6 , or R 5b is O − or OH and R 5a is OR 6 ;
R 3 , R 4 and R 6 are each independently a C 1 -C 4 alkyl;
Hal − is a halide anion selected from the group consisting of bromide (Br − ), chloride (Cl − ) and iodide (I − );
f, i, j, k and l are each independently an integer from 1 to 100;
g is an integer from 0 to 100;
the ratio of j:l is from about 1:1 to 19:1;
0.1<j/(g+j+l)<1.0; and
wherein n is an integer ranging from 20 to 6000;
the method being carried out in a polar solvent and comprising the steps of:
reacting poly(styrene-co-maleic anhydride) copolymer with N,N-dimethyl-3-amino(C 2 -C 7 )alkyl-1-amine to form poly(styrene-co-N—(N′,N′-dimethylamino-(C 2 -C 7 )alkyl)-maleimide); and
reacting the poly(styrene-co-N—(N′,N′-dimethyl-3-amino(C 2 -C 7 )alkyl)-maleimide) with a C 8 -C 15 alkyl bromide, chloride or iodide to produce the polymer of Formula (I).

9. The method as claimed in claim 8 , wherein the reactions are carried out consecutively in the same solvent.

10. The method as claimed in claim 8 , further including a step of diluting the solution containing the polymer of Formula (I) with a low boiling point solvent which has a boiling point of less than 100° C. at a pressure of 101.325 kPa.

11. The method as claimed in claim 8 , wherein about 80-90 mol % of the total maleic anhydride residues in the poly(styrene-co-maleic anhydride) copolymer are converted into N—(N′,N′-dimethyl-3-amino(C 2 -C 7 )alkyl)-maleimide residues and 10%-20% of the maleic anhydride residues remain unmodified.

12. The method as claimed in claim 8 , wherein the poly(styrene-co-maleic anhydride) copolymer is reacted with N,N-dimethyl-3-aminopropyl-1-amine to form poly(styrene-co-N—(N′,N′-dimethylaminopropyl)-maleimide and the poly(styrene-co-N—(N′,N′-dimethyl-3-aminopropyl)-maleimide) is reacted with 1-bromodecane.

13. A method of producing an antimicrobial substrate comprising the steps of:
at least partially coating a substrate or a surface thereof with the solution of claim 1 ; and
curing the coating to crosslink the polymer of Formula (I) to the substrate.

14. An antimicrobial substrate which includes a polymer of

Formula (I)
wherein R 1 is a C 2 -C 7 alkyl;
R 2 is a C 8 -C 15 alkyl;
R 5a is O − or OH and R 5b is OR 6 , or R 5b is O − or OH and R 5a is OR 6 ;
R 3 , R 4 and R 6 are each independently a C 1 -C 4 alkyl;
Hal − is a halide anion selected from the group consisting of bromide (Br − ), chloride (Cl − ) and iodide (I − );
f, i, j, k and l are each independently an integer from 1 to 100;
g is an integer from 0 to 100;
0.1<j/(g+j+l)<1.0; and
n is an integer from about 20 to about 6000;
crosslinked to a substrate.

15. An antimicrobial substrate as claimed in claim 14 in which the substrate is a wound dressing, gauze, burn dressing, sponge, a medical or sanitary wipe, surgical gown, surgical glove, surgical scrubs, upholstery, floor mat, sheet, cover, liner, curtain or insole.

Assignees

• Univ Stellenbosch

Inventors

• Cloete William
• Klumperman Lubertus

Classifications

• C08F8/44

  Preparation of metal salts or ammonium salts · CPC title

• C08F8/32

  by reaction with amines · CPC title

• A01N27/00

  Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons · CPC title

• A61L2300/208

  Quaternary ammonium compounds · CPC title

• C09D125/08

  Copolymers of styrene (C09D129/08, C09D135/06, C09D155/02 take precedence) · CPC title