Comb polymers which can be used in cosmetics and detergents

Patent metadata

Field	Value
Publication number	US-9499648-B2
Application number	US-201414760144-A
Country	US
Kind code	B2
Filing date	Jan 29, 2014
Priority date	Jan 31, 2013
Publication date	Nov 22, 2016
Grant date	Nov 22, 2016

Abstract

A water-soluble copolymer comprising, by mass relative to the total mass of the copolymer:
1 to 40% of at least one cationic monomer; 59.99 to 98% of at least one nonionic monomer; 0.01 to 10% of at least one monomer of formula (I);

in which:
R 1 is a hydrogen atom or a methyl radical; Z is a divalent group —C(═O)—O—, or —C(═O)—NH—; n is an integer between 2 and 200; R 2 is a hydrogen atom or a carbon-containing radical which is saturated or unsaturated, optionally aromatic, linear, branched or cyclic, comprising 1 to 30 carbon atoms, and from 0 to 4 heteroatoms chosen from the group comprising O, N and S;

the copolymer having a cationic charge density between 0.05 and 3 meq/g.

First claim

The invention claimed is:

1. A water-soluble copolymer comprising, by mass relative to the total mass of the copolymer, units derived from:
22.5 to 30% of at least one cationic monomer whose cationicity comes exclusively from one or more quaternary ammonium functional groups;
60 to 70% of at least one nonionic monomer;
0.01 to 10% of at least one monomer of formula (I);

in which:
R 1 is a hydrogen atom or a methyl radical;
Z is a functional group selected from the group consisting of a covalent bond, an oxygen atom, the divalent group —CH 2 —O—, —C(═O)—O—, and —C(═O)—NH—;
n is an integer between 2 and 200;
R 2 is a hydrogen atom or a carbon-containing radical which is saturated or unsaturated, optionally aromatic, linear, branched or cyclic, comprising 1 to 30 carbon atoms, and from 0 to 4 heteroatoms selected from the group consisting of O, N and S;

the copolymer having a cationic charge density between 0.05 and 3 meq/g.

2. The copolymer as claimed in claim 1 , wherein the copolymer has a cationic charge density between 0.05 and 1.8 meq/g.

3. The copolymer as claimed in claim 1 , wherein the monomer of formula (I) is selected from the group consisting of:
poly(ethylene glycol) (meth)acrylate in which R 1 =H or CH 3 ; Z=C(═O)—O—; R 2 =H; n=2 to 200;
methyl-poly(ethylene glycol) (meth)acrylate, in which R 1 =H or CH 3 ; Z=C(═O)—O—; R 2 =CH 3 ; n=2 to 200;
alkyl-poly(ethylene glycol) (meth)acrylates in which R 1 =H or CH 3 ; Z=C(═O)—O—; R 2 =C 1 -C 30 alkyl; n=2 to 200;
phenyl-poly(ethylene glycol) (meth)acrylates, in which R 1 =H or CH 3 ; Z=C(═O)—O—; R 2 =phenyl; n=2 to 200;
poly(ethylene glycol) vinyl alkylenes, in which R 1 =H or CH 3 ; Z=—CH 2 —O—; R 2 =H or C 1 -C 30 alkyl; with n=2 to 200; and
poly(ethylene glycol) oxyvinyl butylenes, in which R 1 =H or CH 3 ; Z=covalent bond; R 2 =H or C 1 -C 30 alkyl; with n=2 to 200.

4. The copolymer as claimed in claim 3 , wherein the monomer of formula (I) is selected from the group consisting of poly(ethylene glycol) (meth)acrylates and methyl-poly(ethylene glycol) (meth)acrylates, having a molar mass between 80 and 8000 g/mol.

5. The copolymer as claimed in claim 1 , wherein the cationic monomer is selected from the group consisting of quaternized dimethylaminoethyl acrylate (ADAME), quaternized dimethylaminoethyl methacrylate (MADAME), dimethyldiallylammonium chloride (DADMAC), acrylamidopropyltrimethylammonium chloride (APTAC) and methacrylamidopropyltrimethylammonium chloride (MAPTAC).

6. The copolymer as claimed in claim 1 , wherein the nonionic monomer is selected from the group consisting of acrylamide, methacrylamide, N-isopropylacrylamide, N,N-dimethylacrylamide, N-methylol acrylamide, N-vinylformamide, N-vinylacetamide, N-vinylpyridine, N-vinylpyrrolidone, acryloylmorpholine (ACMO) and diacetone acrylamide.

7. The copolymer according to claim 1 , wherein n is an integer between 7 and 45.

8. A cosmetic or detergent formulation comprising the copolymer according to claim 1 .

9. The copolymer as claimed in claim 2 , wherein the monomer of formula (I) is selected from the group consisting of:
poly(ethylene glycol) (meth)acrylate in which R 1 =H or CH 3 ; Z=C(═O)—O—; R 2 =H; n=2 to 200;
methyl-poly(ethylene glycol) (meth)acrylate, in which R 1 =H or CH 3 ; Z=C(═O)—O—; R 2 =CH 3 ; n=2 to 200;
alkyl-poly(ethylene glycol) (meth)acrylates in which R 1 =H or CH 3 ; Z=C(═O)—O—; R 2 =C 1 -C 30 alkyl; n=2 to 200;
phenyl-poly(ethylene glycol) (meth)acrylates, in which R 1 =H or CH 3 ; Z=C(═O)—O—; R 2 =phenyl; n=2 to 200;
poly(ethylene glycol) vinyl alkylenes, in which R 1 =H or CH 3 ; Z=—CH 2 —O—; R 2 =H or C 1 -C 30 alkyl; with n=2 to 200; and
poly(ethylene glycol) oxyvinyl butylenes, in which R 1 =H or CH 3 ; Z=covalent bond; R 2 =H or C 1 -C 30 alkyl; with n=2 to 200.

10. The copolymer as claimed in claim 9 , wherein the monomer of formula (I) is selected from the group consisting of poly(ethylene glycol) (meth)acrylates and methyl-poly(ethylene glycol) (meth)acrylates, having a molar mass between 80 and 8000 g/mol.

11. The copolymer as claimed in claim 9 , wherein the cationic monomer is selected from the group consisting of quaternized dimethylaminoethyl acrylate (ADAME), quaternized dimethylaminoethyl methacrylate (MADAME), dimethyldiallylammonium chloride (DADMAC), acrylamidopropyltrimethylammonium chloride (APTAC), and methacrylamidopropyltrimethylammonium chloride (MAPTAC).

12. The copolymer as claimed in claim 9 , wherein the nonionic monomer is selected from the group consisting of acrylamide, methacrylamide, N-isopropylacrylamide, N,N-dimethylacrylamide, N-methylol acrylamide, N-vinylformamide, N-vinylacetamide, N-vinylpyridine, N-vinylpyrrolidone, acryloylmorpholine (ACMO) and diacetone acrylamide.

13. A method of improving the formation of coacervates in a cosmetic or detergent formulation, the method comprising incorporating the copolymer according to claim 1 into a cosmetic or detergent formulation.

14. The method according to claim 13 , wherein the monomer of formula (I) is selected from the group consisting of:
poly(ethylene glycol) (meth)acrylate in which R 1 =H or CH 3 ; Z=C(═O)—O—; R 2 =H; n=2 to 200;
methyl-poly(ethylene glycol) (meth)acrylate, in which R 1 =H or CH 3 ; Z=C(═O)—O—; R 2 =CH 3 ; n=2 to 200;
alkyl-poly(ethylene glycol) (meth)acrylates in which R 1 =H or CH 3 ; Z=C(═O)—O—; R 2 =C 1 -C 30 alkyl; n=2 to 200;
phenyl-poly(ethylene glycol) (meth)acrylates, in which R 1 =H or CH 3 ; Z=C(═O)—O—; R 2 =phenyl; n=2 to 200;
poly(ethylene glycol) vinyl alkylenes, in which R 1 =H or CH 3 ; Z=—CH 2 —O—; R 2 =H or C 1 -C 30 alkyl; with n=2 to 200; and
poly(ethylene glycol) oxyvinyl butylenes, in which R 1 =H or CH 3 ; Z=covalent bond; R 2 =H or C 1 -C 30 alkyl; with n=2 to 200.

15. A water-soluble copolymer comprising, by mass relative to the total mass of the copolymer, units derived from:
22.5 to 30% of at least one cationic monomer whose cationicity comes exclusively from one or more quaternary ammonium functional groups;
60 to 80% of at least one nonionic monomer;
0.01 to 10% of at least one monomer of formula (I);

in which:
R 1 is a hydrogen atom or a methyl radical;
Z is a functional group selected from the group consisting of a covalent bond, an oxygen atom, the divalent group —CH 2 —O—, —C(═O)—O—, and —C(═O)—NH—;
n is an integer between 2 and 200;
R 2 is a hydrogen atom or a carbon-containing radical which is saturated or unsaturated, optionally aromatic, linear, branched or cyclic, comprising 1 to 30 carbon atoms, and from 0 to 4 heteroatoms selected from the group consisting of O, N and S;

the copolymer having a cationic charge density between 0.05 and 3 meq/g,
wherein the monomer of formula (I) is selected from the group consisting of:
poly(ethylene glycol) (meth)acrylate in which R 1 =H or CH 3 ; Z=C(═O)—O—; R 2 =H; n=2 to 200;
methyl-poly(ethylene glycol) (meth)acrylate, in which R 1 =H or CH 3 ; Z=C(═O)—O—; R 2 =CH 3 ; n=2 to 200;
alkyl-poly(ethylene glycol) (meth)acrylates in which R 1 =H or CH 3 ; Z=C(═O)—O—; R 2 =C 1 -C 30 alkyl; n=2 to 200;
phenyl-poly(ethylene glycol) (meth)acrylates, in which R 1 =H or CH 3 ; Z=C(═O)—O—; R 2 =phenyl; n=2 to 200;
poly(ethylene glycol) vinyl alkylenes, in which R 1 =H or CH 3 ; Z=—CH 2 —O—; R 2 =H or C 1 -C 30 alkyl; with n=2 to 200; and
poly(ethylene glycol) oxyvinyl butylenes, in which R 1 =H or

Assignees

• Spcm Sa

Inventors

• Blondel Frédéric
• Sanna Antonin

Classifications

• A61Q19/00

  Preparations for care of the skin · CPC title

• A61K2800/5426

  cationic · CPC title

• A61K8/8158

  Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers · CPC title

• C08F220/285

  and containing a polyether chain in the alcohol moiety · CPC title

• C08F226/02

  by a single or double bond to nitrogen · CPC title