Ampholytic polymers having a thermosensitive character

Patent metadata

Field	Value
Publication number	US-10131729-B2
Application number	US-201314654679-A
Country	US
Kind code	B2
Filing date	Nov 26, 2013
Priority date	Dec 21, 2012
Publication date	Nov 20, 2018
Grant date	Nov 20, 2018

Abstract

A comb copolymer with a polymer backbone having grafted lateral macromonomer segments, the method of preparing, and the use thereof as a thickener in cosmetics. The polymer backbone is more than 55% and up to 90% molar ATBS, between 1% and 20% molar cationic monomer or monomer of formula (I): CH 2 ═C(R 1 )—C(═O)—Y—(CH 2 )m-N(R 2 ) (R 3 ), where m is between 1 and 4, Y is O or NH, R1 is H or CH 2 , and R 2 and R 3 are each a methyl or ethyl radical, and optionally 0.005% to 1% molar of at least one cross-linking monomer with at least two C═C bonds. The lateral macromonomer segments are polymerized from 9% to 30% molar of N-alkyl acrylamide or N,N-dialkyl acrylamide of formula (II): CH 2 ═C(R 4 )—C(═O)—N(R 5 ) (R 6 ), where R 4 is H or CH 2 and R 5 and R 6 are H or a C 1 to C 3 alkyl radical, with at least one of R 5 or R 6 not being H.

First claim

The invention claimed is:

1. A comb copolymer consisting of a polymer backbone to which macromonomeric side segments are grafted, wherein said polymer backbone consists, for 100 mol % of constituent monomer units of said comb copolymer:
of more than 55 mol %, up to 90 mol % of monomer units resulting from 2-methyl 2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid (hereinafter denoted ATBS), which is free, partially salified or completely salified;
of 1 mol % to 20 mol % of monomeric units resulting from a monomer of dimethylaminoethyl methacrylate or N-[3-(dimethylamino)propyl]acrylamide;
optionally of 0.005 mol % to 1 mol % of monomer units resulting from at least one crosslinking monomer comprising at least two carbon-carbon double bonds,
and said macromonomeric side segments result, for 100 mol % constituent of said comb copolymer, from the polymerization of 9 mol % to 30 mol % of an N-alkylacrylamide selected from the group consisting of N-methylmethacrylamide, N-ethylmethacrylamide, N-propylmethacrylamide, N-isopropylmethacrylamide, N-(2-hydroxyethyl)methacrylamide, N-methylacrylamide, N-ethylacrylamide, N-propylacrylamide, N-isopropylacrylamide, and N-(2-hydroxyethyl)acrylamide.

2. The comb copolymer as defined in claim 1 , wherein the N-alkylacrylamide is N-isopropylacrylamide.

3. The comb copolymer as defined in claim 1 , wherein the monomer units resulting from 2-methyl 2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid (hereinafter denoted ATBS) are 60 mol % to 80 mol % of the comb copolymer.

4. The comb copolymer as defined in claim 1 , wherein the monomeric units resulting from a monomer of dimethylaminoethyl methacrylate or N-[3-(dimethylamino)propyl]acrylamide are 4 mol % to 15 mol % of the comb copolymer.

5. The comb copolymer as defined in claim 1 , wherein the monomer units resulting from at least one crosslinking monomer comprising at least two carbon-carbon double bonds are 0.01 mol % to 0.5 mol % of the comb copolymer.

6. The comb copolymer as defined in claim 1 , wherein the macromonomeric side segments result from the polymerization of 15 mol % to 25 mol % of said N-alkylacrylamide.

7. A process for preparing the comb copolymer as defined in claim 1 , comprising the steps of:
(a) reacting:
an N-alkylacrylamide compound selected from the group consisting of N-methylmethacrylamide, N-ethylmethacrylamide, N-propylmethacrylamide, N-isopropylmethacrylamide, N-(2-hydroxyethyl)methacrylamide, N-methylacrylamide, N-ethylacrylamide, N-propylacrylamide, N-isopropylacrylamide, and N-(2-hydroxyethyl)acrylamide, said N-alkylacrylamide compound being defined according to formula (II):
CH 2 ═C(R 2 )—C(═O)—N(R 3 )(R 4 )  (II),

in which, depending on said N-alkylacrylamide compound, R 2 represents a hydrogen atom or a methyl group, R 3 represents a hydrogen atom and R 4 represents a linear or branched alkyl radical comprising from 1 to 3 carbon atoms, optionally substituted by a hydroxyl group,
with
a chain-limiting compound of formula (IVa):
HS—R 1 —NH 2   (IVa)

or of formula (IVb):
HS—R 1 —C(═O)—OH  (IVb)

in which formula (IVa) or (IVb) R 1 represents a divalent radical comprising from 1 to 4 carbon atoms, in the presence of a polymerization initiator, in a tert-butanol/water mixture,
in order to obtain a poly(N-alkylacrylamide) telomer of formula (Va):
H 2 N—R 1 —S—{CH 2 —C(R 2 )[C(═O)N(R 3 )(R 4 )]−} n —H  (Va)

or of formula (Vb):
HO—C(═O)—R 1 —S—{CH 2 —C(R 2 )[C(═O)N(R 3 )(R 4 )]—} n —H  (Vb),

in which formula (Va) or (Vb) n represents an integer of greater than or equal to 2 and less than or equal to 100;
optionally (b) isolating and/or drying of said telomer of formula (Va) or of formula (Vb) obtained in step (a);
(c) reacting in tert-butanol of the telomer of formula (Va) or of formula (Vb) obtained in step (a), or optionally in step (b), with glycidyl methacrylate (VI) and in a (VI)/(IVa) or (VI)/(IVb) molar ratio of less than or equal to 10 and greater than or equal to 1, while maintaining the pH of the reaction medium at a value of greater than 10 and less than or equal to 13 in order to obtain, after adjustment of the pH to a value of greater than or equal to 7 and less than or equal to 9 a solution of the macromonomer of formula (VIIa):
CH 2 ═C(CH 3 )—C(═O)—NH—R 1 —S—{CH 2 —C(R 2 )[C(═O)N(R 3 )(R 4 )]—} n —H   (VIIa);

or of formula (VIIb):
CH 2 ═C(CH 3 )—C(═O)—O—(C═O)—R 1 —S—{CH 2 —C(R 2 )[C(═O)N(R 3 )(R 4 )]—} n —H   (VIIb);

optionally (d) isolating and/or drying of said macromonomer of formula (VIIa) or of formula (VIIb) obtained in step (c);
(e) copolymerizing in tert-butanol of said macromonomer of formula (VIIa) or of formula (VIIb) resulting from step (c) or from optional step (d) with 2-acrylamido-2-methylpropanesulfonic acid and dimethylaminoethyl methacrylate or N-[3-(dimethylamino)propyl]acrylamide, and optionally with at least one crosslinking monomer comprising at least two carbon-carbon double bonds in the desired molar proportions, and,
optionally (f) purifying the comb copolymer obtained in step (e).

8. A method for caring for and/or conditioning the hair, comprising applying an effective amount of a cosmetic or pharmaceutical composition comprising the comb copolymer as defined in claim 1 .

9. A cosmetic or pharmaceutical composition, comprising, as thickening agent, an effective amount of the comb copolymer as defined in claim 1 .

Assignees

• Soc Dexploitation De Produits Pour Les Industries Chimiques Seppic

Inventors

• Mallo Paul
• Braun Olivier

Classifications

• A61K2800/54

  Polymers characterized by specific structures/properties · CPC title

• A61K8/91

  Graft copolymers (A61K8/89 takes precedence) · CPC title

• A61Q5/06

  Preparations for styling the hair, e.g. by temporary shaping or colouring · CPC title

• A61Q5/12

  Preparations containing hair conditioners · CPC title

• A61Q5/00

  Preparations for care of the hair · CPC title