Ethylene copolymers, compositions comprising same and preparation and treatment methods

Patent metadata

Field	Value
Publication number	US-9359461-B2
Application number	US-63111405-A
Country	US
Kind code	B2
Filing date	Jul 1, 2005
Priority date	Jul 2, 2004
Publication date	Jun 7, 2016
Grant date	Jun 7, 2016

Abstract

The invention concerns novel ethylene copolymers comprising polyethylene glycol (meth)acrylate monomers, cationic monomers, and optionally amphoteric, anionic and/or hydrophilic nonionic monomers, neutralized by particular neutralizing agents. The invention also concerns composition in particular cosmetic or pharmaceutical comprising said copolymers, as well as methods for preparing said copolymers, and cosmetic treatment methods using same.

First claim

The invention claimed is:

1. An ethylenic copolymer comprising, as a weight percentage relative to the total weight of the copolymer:
a) 10-80% by weight of at least one monomer of formula (I):

and salts thereof, wherein:
R 1 is chosen from hydrogen and linear or branched hydrocarbon-based radicals of the formula C p H 2p+1 , where p is an integer ranging from 1 to 12;
Z is a divalent group chosen from —COO—, —CONH—, —CONCH 3 —, —OCO—, —O—, —SO 2 —, —CO—O—CO—, and —CO—CH 2 —CO—;
x is 0 or 1;
R 2 is chosen from saturated or unsaturated, optionally aromatic, linear, branched or cyclic C 1 -C 30 carbon-based divalent radicals optionally comprising 1 to 18 heteroatoms chosen from O, N, S, F, Si, and P;
m is 0 or 1;
n is an integer ranging from 3 to 300;
R 3 is chosen from hydrogen and saturated or unsaturated, optionally aromatic, linear, branched, or cyclic C 1 -C 30 carbon-based radicals optionally comprising 1 to 20 heteroatoms chosen from O, N, S, F, Si, and P;

b) 20-90% by weight of at least one cationic monomer chosen from monomers of formula (IIa):

and salts thereof, wherein:
R 1 is chosen from hydrogen and linear or branched hydrocarbon-based radicals of the formula C p H 2p+1 , where p is an integer ranging from 1 to 12;
Z′ is a divalent group chosen from —COO—, —CONH—, —CONCH 3 —, —OCO—, —O—, —SO 2 —, —CO—O—CO—, and —CO—CH 2 —CO—;
x′ is 0 or 1;
R 2 ′ is chosen from saturated or unsaturated, optionally aromatic, linear, branched or cyclic C 1 -C 30 divalent carbon-based radicals, optionally comprising 1 to 18 heteroatoms chosen from O, N, S, F, Si, and P;
m′ is 0 or 1;
X is chosen from:
(a) guanidino and amidino groups;
(b) —N(R 6 )(R 7 ), —P(R 6 )(R 7 ), and —P + R 6 R 7 R 8 groups, wherein R 6 , R 7 , and R 8 are independently chosen from:
hydrogen;
linear, branched or cyclic, saturated or unsaturated, optionally aromatic C 1 -C 18 alkyl radicals optionally comprising 1 to 10 heteroatoms chosen from O, N, S, F, Si, and P;
R 6 and R 7 may form, together with the nitrogen or phosphorus atom, a first saturated or unsaturated, optionally aromatic ring comprising a total of 5 to 8 atoms and optionally 2 to 4 heteroatoms chosen from O, S, and N, wherein the first ring is optionally fused with at least one saturated or unsaturated, optionally aromatic ring comprising 5 to 7 atoms and optionally 2 to 4 heteroatoms chosen from 0, S, and N; and

(c) —R′ 6 —N—R′ 7 — groups, where R′ 6 and R′ 7 form, together with the nitrogen atom, a second saturated or unsaturated, optionally aromatic ring comprising a total of 5 to 8 atoms and optionally 2 to 4 heteroatoms chosen from O, S, and N, wherein the second ring is optionally fused with at least one saturated or unsaturated, optionally aromatic ring comprising 5 to 7 atoms and optionally 2 to 4 heteroatoms chosen from 0, S, and N,

wherein the ethylenic copolymer is noncrosslinked and at least partially neutralized with at least one neutralizer chosen from organic Brönsted acids.

2. The ethylenic copolymer of claim 1 , wherein R 1 is chosen from hydrogen, methyl, ethyl, propyl, and butyl.

3. The ethylenic copolymer of claim 1 , wherein Z′ is chosen from —COO— and —CONH—.

4. The ethylenic copolymer of claim 1 , wherein R 2 is chosen from:
alkylene radicals chosen from methylene, ethylene, propylene, n-butylene, isobutylene, tert-butylene, n-hexylene, n-octylene, n-dodecylene, n-octadecylene, n-tetradecylene, and n-docosanylene;
ortho, meta, and para phenylene radicals of the formula —C 6 H 4 —, optionally substituted with at least one group chosen from:
C 1 -C 12 alkyl radicals, optionally comprising 1 to 25 heteroatoms chosen from O, N, S, F, Si, and P; and
benzylene radicals —C 6 H 4 —CH 2 — optionally substituted with at least one C 1 -C 12 alkyl radical optionally comprising 1 to 8 heteroatoms chosen from O, N, S, F, Si, and P;

pyridinium radicals of the formula:

wherein R′ 1 , R′ 2 , R′ 3 , and R′ 4 are independently chosen from hydrogen and C 1 -C 12 alkyl radicals optionally comprising 1 to 8 heteroatoms chosen from O, N, S, F, Si, and P; and
radicals chosen from —CH 2 —O—CO—O—, CH 2 —CH 2 —O—CO—O—, —CH 2 —CO—O—, —CH 2 —CH 2 —CO—O—, —CH 2 —O—CO—NH—, —CH 2 —CH 2 —O—CO—NH—, —CH 2 —NH—CO—NH—, —CH 2 —CH 2 —NH—CO—NH—, —CH 2 —CHOH—, —CH 2 —CH 2 —CHOH—, CH 2 —CH 2 —CH(NH 2 )—, —CH 2 —CH(NH 2 )—, —CH 2 —CH 2 —CH(NHR′)—, —CH 2 —CH(NHR′)—, —CH 2 —CH 2 —CH(NR′R″)—, —CH 2 —CH(NR′R″)—, —CH 2 —CH 2 —CH 2 —NR′—, —CH 2 —CH 2 —CH 2 —O—, and —CH 2 —CH 2 —CHR′—O—, wherein R′ and R″ are independently chosen from linear or branched C 1 -C 22 alkyl radicals optionally comprising 1 to 12 heteroatoms chosen from O, N, S, F, Si, and P;
and mixtures thereof.

5. The ethylenic copolymer of claim 1 , wherein n ranges from 9 to 50.

6. The ethylenic copolymer of claim 1 , wherein R 3 is chosen from
hydrogen, succinimido, maleimido, mesityl, tosyl, triethoxysilane, phthalimide, and —CH 2 —CH 2 CN radicals;
benzyl and phenyl radicals, each optionally substituted with at least one C 1 -C 12 alkyl radical optionally comprising 1 to 8 heteroatoms chosen from O, N, S, F, Si, and P; and
C 1 -C 30 alkyl radicals optionally comprising 1 to 18 heteroatoms chosen from O, N, S, F, Si, and P,
wherein the benzyl, phenyl or alkyl radicals are optionally substituted with at least one group chosen from succinimido, glutarate-succinimid, glutarate, maleimido, mesityl, benzoate, tosyl, triethoxysilane, phthalimide, thioester, benzotriazole carbonate, butyraldehyde, acetaldehyde diethyl acetal, biotin, phospholipid, succinate, N-hydroxysuccinimide, —SO 3 H, —COOH, —PO 4 , —NR 5 R 6 , and —N + R 5 R 6 R 7 , wherein R 5 , R 6 , and R 7 are independently chosen from hydrogen and linear, branched or cyclic C 1 -C 18 alkyl radicals optionally comprising at least one group chosen from heteroatoms and protecting groups.

7. The ethylenic copolymer of claim 6 , wherein the C 1 -C 30 alkyl radicals are chosen from C 2 -C 16 alkyl radicals.

8. The ethylenic copolymer of claim 1 and mixtures thereof, wherein the at least one monomer of formula (I) is chosen from:
poly(ethylene glycol) (meth)acrylate;
methylpoly(ethylene glycol) (meth)acrylate;
alkylpoly(ethylene glycol) (meth)acrylates;
phenylpoly(ethylene glycol) (meth)acrylates; and
monomers of the formula:

wherein n ranges from 3 to 100.

9. The ethylenic copolymer of claim 1 , wherein the at least one monomer of formula (I) has a molecular weight ranging from 350 to 13000 g/mol.

10. The ethylenic copolymer of claim 1 , wherein the at least one monomer of formula (I) is chosen from poly(ethylene glycol) (meth)acrylates and methylpoly(ethylene glycol) (meth)acrylates.

11. The ethylenic copolymer of claim 1 , wherein the at least one monomer of formula (I) is chosen from poly(ethylene glycol) (meth)acrylates having a molecular weight ranging from 500 to 8000 g/mol.

12. The ethylenic copolymer of claim 1 , wherein the at least one monomer of formula (I) is present in the copolymer, alone or as a mixture, in an amount ranging from 30% to 50% by weight, relative to the total weight of the ethylenic copolymer.

13. The ethylenic copolymer of claim 1 , wherein R′ 2 is c

Assignees

• Mougin Nathalie
• Jegou Gwenaëlle
• Oreal

Inventors

• Mougin Nathalie
• Jegou Gwenaëlle

Classifications

• C08F220/60

  containing nitrogen in addition to the carbonamido nitrogen · CPC title

• A61Q5/065

  Preparations for temporary colouring the hair, e.g. direct dyes · CPC title

• C08F220/26

  Esters containing oxygen in addition to the carboxy oxygen · CPC title

• A61K8/8158

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

• A61Q5/12

  Preparations containing hair conditioners · CPC title