Self-disinfecting surfaces

Patent metadata

Field	Value
Publication number	US-2018002533-A1
Application number	US-201715703104-A
Country	US
Kind code	A1
Filing date	Sep 13, 2017
Priority date	Feb 1, 2013
Publication date	Jan 4, 2018
Grant date	—

Abstract

The invention relates to an aqueous coating composition comprising a compound having reactive groups A, and a quaternary ammonium compound according to Formula I, II or III

wherein
R 1 is an alkyl, alkenyl, alkylaryl or arylalkyl group having from 5 to 50 carbon atoms;
R 2 is a C 1 -C 100 hydrocarbyl group, optionally containing heteroatoms;
R 3 and R 4 are alkylene groups having from 1 to 4 carbon atoms;
R 5 and R 6 are H or C 1 -C 100 hydrocarbyl group, optionally containing heteroatoms;
R 7 is a C 1 -C 100 hydrocarbyl group, optionally containing heteroatoms;
R 8 is a C 1 -C 100 hydrocarbyl group, optionally containing heteroatoms;
R 9 is H or a methyl group;
Z is a substituent containing at least one reactive group B which is capable of reacting with the reactive group A;
X − is an anion;
y is 0 or 1;
a is 0 or 1; and the sum of y and a is 1 or 2 and
m is an integer from 1 to 30, preferably between 1 and 10, or between 2 and 6
n is an integer from 0-30, preferably between 1 and 10, or 2 and 6
T is a monomer unit;
U is a monomer unit;
V is a C 1 -C 100 hydrocarbyl group, optionally containing hetero atoms;
d is an integer between 1 and 5, preferably 1;
e is an integer between 1 and 1000, preferably between 5 and 100;
g is an integer between 1 and 100, preferably between 2 and 10;
h is an integer between 1 and 5, preferably 2 or 3.

First claim

1 . (canceled)

2 . (canceled)

3 . (canceled)

4 . (canceled)

5 . (canceled)

6 . An aqueous coating composition comprising a compound having reactive groups A, and a quaternary ammonium compound according to Formula I, II or III

wherein
R 1 is an alkyl, alkenyl, alkylaryl or arylalkyl group having from 5 to 50 carbon atoms;
R 2 is a C 1 -C 100 hydrocarbyl group, optionally containing heteroatoms;
R 3 and R 4 are alkylene groups having from 1 to 4 carbon atoms;
R 5 and R 6 are H or C 1 -C 100 hydrocarbyl group, optionally containing heteroatoms;
R 7 is a C 1 -C 100 hydrocarbyl group, optionally containing heteroatoms;
R 8 is a C 1 -C 100 hydrocarbyl group, optionally containing heteroatoms;
R 9 is H or a methyl group;
Z is a substituent containing at least one reactive group B which is capable of reacting with the reactive group A, wherein the at least one reactive group B is independently selected from the group consisting of hydroxyl, carboxylic acid, aldehyde, anhydride, ester, ethyleneimine, amine, amide, thiol, epoxide, urea, acetoacetate, and isocyanate groups;
X − is an anion;
m is an integer from 1 to 30;
n is an integer from 0-30;
T is a monomer unit;
U is a monomer unit;
V is a C 1 -C 100 hydrocarbyl group, optionally containing hetero atoms;
d is an integer between 1 and 5;
e is an integer between 1 and 1000;
g is an integer between 1 and 100;
h is an integer between 1 and 5.

7 . The coating composition according to claim 6 , wherein reactive groups A are chosen from the group consisting of hydroxyl, carboxylic acid, urea, acetoacetates, aldehyde, isocyanate, ethyleneimine, anhydride, ester, acrylate, methacrylate, amine, amide, thiol, epoxide or vinyl groups.

8 . The coating composition according to claim 6 , wherein the compound having reactive groups A comprises at least one polymer selected from the group consisting of poly(lactams), in particular polyvinylpyrrolidones; polyurethanes; polyureas; homo- and copolymers of acrylic and methacrylic acid; polyvinyl alcohols; polyvinylethers; maleic anhydride based copolymers; polyesters; vinylamines; polyethyleneimines; polyethylene oxides; poly(carboxylic acids); polyamides; polyanhydrides; polyphosphazenes; cellulosics; chondroitin sulphates; (poly)peptides/proteins; polyesters; and polynucleotides.

9 . The coating composition according to claim 6 , wherein the compound having reactive groups A comprises a crosslinker selected from aziridine, carbodiimid, melamine, substituted melamine, melamine derivative, multifunctional alcohol, multifunctional aldehyde, multifunctional amine, multifunctional isocyanate, multifunctional epoxide and combinations thereof.

10 . (canceled)

11 . The coating composition according to claim 6 , wherein the ratio Q AB of the molar amount of reactive groups A and the molar amount of reactive groups B is between 0.1 and 2.

12 . The coating composition according to claim 6 , wherein R 3 and R 4 are alkylene groups having from 1-4 carbon atoms.

13 . The coating composition according to claim 6 , wherein the quaternary ammonium compound is present in the coating composition in an amount between 5 wt % and 70 wt % based on the total weight of the coating composition excluding the carrier liquid.

14 . The coating composition according to claim 6 , wherein the liquid coating composition has a low anti-microbial activity, wherein the low anti-microbial activity is defined as less than 20% inhibition of bacterial growth of pseudomonas aeruginosa , according to ISO/FDIS 20776-1 (2006).

15 . The coating composition according to claim 6 , wherein X − is an anion chosen from sulphate, nitrate, phosphate, acetate or halogen.

16 . A process for preparing an anti-microbial coating on a substrate, by applying a coating composition according to claim 6 on a substrate and subsequently curing the coating compositions to prepare the coating.

17 . An article comprising an anti-microbial coating that is prepared by
a. applying a coating composition comprising a quaternary ammonium compound having an alkoxylated substituent having a reactive group B according to formula (I), (II), or (III) to a substrate, and b. curing the coating composition to obtain a cured coating,
wherein the reactive group B of the alkoxylated substituent has reacted within the cured coating,

wherein:
R 1 is an alkyl, alkenyl, alkylaryl or arylalkyl group having from 5 to 50 carbon atoms;
R 2 is a C 1 -C 100 hydrocarbyl group, optionally containing heteroatoms;
R 3 is a C 1 -C 4 alkylene group;
R 4 is a C 1 -C 4 alkylene group;
R 5 and R 6 are H or C 1 -C 100 hydrocarbyl group, optionally containing heteroatoms;
R 7 is a C 1 -C 100 hydrocarbyl group, optionally containing heteroatoms;
R 8 is a C 1 -C 100 hydrocarbyl group, optionally containing heteroatoms;
R 9 is H or methyl;
Z is a substituent containing at least one reactive group B, wherein the at least one reactive group B is independently selected from the group consisting of hydroxyl, carboxylic acid, aldehyde, anhydride, ester, ethyleneimine, amine, amide, thiol, epoxide, urea, acetoacetate, and isocyanate groups;
X − is an anion;
m is an integer from 1 to 30;
n is an integer from 1 to 30; and
T is a monomer unit;
U is a monomer unit;
V is a C 1 -C 100 hydrocarbyl group, optionally containing hetero atoms;
d is an integer between 1 and 5;
e is an integer between 1 and 1000;
g is an integer between 1 and 100;
h is an integer between 1 and 5,
wherein the surface of the coating contains quaternary ammonium groups having alkoxy substituents.

18 . The article according to claim 17 , wherein the coating has a surface charge on the coatings is above of 1×10 15 /cm 2 .

19 . (canceled)

20 . (canceled)

21 . (canceled)

22 . The coating composition according to claim 6 , wherein the quaternary ammonium compound according to Formula I, II or III is a quaternary ammonium compound according to formula (Ia),

wherein R 9 is H or methyl;
R 1 is a linear alkyl group having from 10-15 carbon atoms;
R 2 is a C 1 -C 100 hydrocarbyl group, optionally containing heteroatoms;
R 3 is a C1-C4 alkylene group;
R 4 is a C1-C4 alkylene group;
Z is a substituent containing at least one reactive group B which is capable of reacting with the reactive group A, wherein the at least one reactive group B is independently selected from the group consisting of hydroxyl, carboxylic acid, aldehyde, anhydride, ester, ethyleneimine, amine, amide, thiol, epoxide, urea, acetoacetate, and isocyanate groups;
m is an integer from 1 to 30;
n is an integer from 1 to 30;
X is an anion, preferably a sulphate, nitrate, phosphate, acetate or a halogen ion.

23 . An article comprising a

Assignees

• Croda Int Plc

Inventors

• Mahmoud Hossein

Classifications

• C07C271/22

  to carbon atoms of hydrocarbon radicals substituted by carboxyl groups · CPC title

• A01N33/12

  Quaternary ammonium compounds · CPC title

• C08K5/19

  Quaternary ammonium compounds · CPC title

• A01N37/06

  Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof · CPC title

• C08K5/0058

  Biocides; (macromolecular substances as carriers for biocide material A01N25/10) · CPC title