High molecular weight mass cationic copolymers

Details High molecular weight mass cationic copolymers High molecular weight mass cationic copolymers

1998-07-24

2004-01-27

Page, Thurman K. (Department: 1616)

Drug, bio-affecting and body treating compositions

Live hair or scalp treating compositions

Polymer containing

C424S070100, C424S070150, C424S070160, C424S070210, C424S401000

Reexamination Certificate

active

06682725

ABSTRACT:

The present invention relates to the use of polymers obtainable by free-radically initiated copolymerization of monomer mixtures comprising
(a) from 1 to 99.99% by weight of a cationic monomer or quaternizable monomer,
(b) from 0 to 98.99% by weight of a water-soluble monomer,
(c) from 0 to 50% by weight of a further free-radically copolymerizable monomer, and
(d) from 0.01 to 10% by weight of a bifunctional or polyfunctional, free-radically copolymerizable monomer,
and subsequent quaternization of the polymer if the monomer (a) employed is a non-quaternized monomer, as active ingredients in cosmetic formulations, preferably in cosmetic hair formulations, especially as conditioning agents in shampoos.
Cationic polymers are employed as conditioning agents in cosmetic formulations. They bring about primarily an improvement in the wet combability of the hair. In addition, cationic polymers prevent electrostatic charging of the hair.
In shampoos, cationic cellulose derivatives (polyquaternium 10) are primarily employed. However, with these compounds a build-up effect is observed; in other words, on repeated use the hair becomes coated with the conditioner and has a heavy feel.
In addition, copolymers of acrylamide and dimethyldiallylammonium chloride (polyquaternium 7) are used. These compounds have the disadvantage, however, of high residual monomer contents, since acrylamide and dimethyldiallylammonium chloride have unfavorable copolymerization parameters.
Quaternized polymers and their use as conditioning agents in haircare formulations are known.
For instance, EP 246 580 describes the use of homo- and copolymers of 3-methyl-1-vinylimidazolium chlorides, inter alia, as hair conditioning agents. EP 544 158 and U.S. Pat. No. 4,859,756 claim the use of homo- and copolymers of chloride-free quaternized N-vinylimidazoles in cosmetic formulations. EP 715 843 discloses the use of copolymers of a quaternized N-vinylimidazole, N-vinylcaprolactam and N-vinylpyrrolidone and, optionally, a further comonomer in cosmetic formulations.
None of said patents describes the use of crosslinked polymers.
DE 3209224 describes the preparation of crosslinked polymers based on N-vinylpyrrolidone and (quaternized) N-vinylimidazole. These polymers are claimed for use as adsorbents and ion exchangers. They are highly crosslinked, insoluble in water and of poor swellability and are therefore unsuitable as conditioning agents in cosmetic formulations.
U.S. Pat. No. 4,058,491 discloses crosslinked cationic hydrogels formed from N-vinylimidazole or N-vinylpyrrolidone and a quaternized basic acrylate along with other comonomers. These gels are proposed for the complexing and controlled release of anionic active substances.
WO 96/26229 describes crosslinked copolymers of N-vinylimidazoles and, inter alia, quaternized N-vinylimidazoles. The polymers are proposed as additives to detergent formulations for inhibiting dye transfer and as adsorbents. They are insoluble in water and unsuitable for cosmetic formulations.
WO 96/37525 describes the preparation of crosslinked copolymers of, inter alia, N-vinylpyrrolidone and quaternized vinylimidazoles in the presence of polymerization regulators, and their use, in particular, in detergents.
DE 4213971 describes copolymers of an unsaturated carboxylic acid, quaternized vinylimidazole and, optionally, further monomers and a crosslinker. The polymers are proposed as thickeners and dispersants.
DE 2821239 (U.S. Pat. No. 4,348,380) describes copolymers of quaternized diallylammonium compounds in cosmetic hair formulations. The polymers are not crosslinked.
DE 3106974 claims a hair treatment composition of the pre-shampoo type, which comprises homo- and copolymers of quaternized diallylammonium compounds. No crosslinker is mentioned.
U.S. Pat. No. 5,275,809, EP 522 755, EP 521 665 and EP 521 666 claim copolymers with dimethyldiallylammonium chloride for use in shampoos. None of these documents describes a crosslinked polymer.
U.S. Pat. No. 4,806,345 cites crosslinked cationic thickeners for cosmetic formulations comprising quaternized dimethylaminoethyl methacrylate and acrylamide.
WO 93/25595 cites crosslinked cationic copolymers based on quaternized dialkylaminoalkyl acrylates or dialkylaminoalkylacrylamides. The proposed use of these crosslinked copolymers is as thickeners in cosmetic formulations, for example in shampoo formulations.
It is an object of the present invention to find a cationic conditioning agent for shampoos which has improved activity and no build-up effect.
We have found that this object is achieved by the crosslinked polymers defined at the outset, which have a very good conditioning action in shampoos, whereas the corresponding non-crosslinked polymers show little activity as conditioning agents in shampoos.
The use in accordance with the invention relates to polymers obtainable by (i) free-radically initiated copolymerization of monomer mixtures comprising
(a) from 1 to 99.99% by weight, preferably from 2 to 70% by weight and, with particular preference, from 2 to 50% by weight of a cationic monomer or quaternizable monomer,
(b) from 0 to 98.99% by weight, preferably from 22 to 97.98% by weight and, with particular preference, from 45 to 97.95% by weight of a water-soluble monomer,
(c) from 0 to 50% by weight, preferably from 0 to 40% by weight and, with particular preference, from 0 to 30% by weight of a further free-radically copolymerizable monomer, and
(d) from 0.01 to 10% by weight, preferably from 0.02 to 8% by weight and, with particular preference, from 0.05 to 5% by weight of a bi- or polyfunctional, free-radically copolymerizable monomer,
and (ii) subsequent quaternization of the polymer if the monomer (a) employed is a non-quaternized monomer, as conditioning agents for compositions in hair cosmetology.
Suitable monomers (a) are the N-vinylimidazole derivatives of the formula (I), in which R
1
to R
3
are hydrogen, C
1
-C
4
-alkyl or phenyl.
Also suitable are diallylamines of the formula (II), in which R
4
is C
1
-C
24
-alkyl.
Additionally suitable are N,N-dialkylaminoalkyl acrylates and methacrylates, and N,N-dialkylaminoalkylacrylamides and -methacrylamides, of the formula (III),
where R
5
and R
6
independently are hydrogen or methyl, R
7
is optionally alkyl-substituted C
1
-C
24
-alkylene and R
8
and R
9
are C
1
-C
24
-alkyl. Z is nitrogen if x=1 or is oxygen if x=0.
Examples of compounds of the formula (III) are
N,N-dimethylaminomethyl (meth)acrylate, N,N-diethylaminomethyl (meth)acrylate, N,N-dimethylaminoethyl (meth)acrylate,
N,N-diethylaminoethyl (meth)acrylate, N,N-dimethylaminobutyl (meth)acrylate, N,N-diethylaminobutyl (meth)acrylate,
N,N-dimethylaminohexyl (meth)acrylate, N,N-dimethylaminooctyl (meth)acrylate, N,N-dimethylaminododecyl (meth)acrylate,
N-[3-(dimethylamino)propyl]methacrylamide,
N-[3-(dimethylamino)propyl]acrylamide, N-[3-(dimethylamino)-butyl]methacrylamide, N-[8-(dimethylamino)octyl]methacrylamide,
N-[12-(dimethylamino)dodecyl]methacrylamide,
N-[3-(diethylamino)propyl]methacrylamide and
N-[3-(diethylamino)propyl]acrylamide.
Examples of compounds suitable for quaternizing the compounds of the formulae (I)-(III) are C
1
-C
24
-alkyl halides, examples being methyl chloride, methyl bromide, methyl iodide, ethyl chloride, ethyl bromide, propyl chloride, hexyl chloride, dodecyl chloride and lauryl chloride, and benzyl halides, especially benzyl chloride and benzyl bromide. Further suitable quaternizing agents are dialkyl sulfates, especially dimethyl sulfate or diethyl sulfate. The basic monomers of the formulae (I)-(III) can also be quaternized with alkylene oxides, such as ethylene oxide or propylene oxide, in the presence of acids.
Quaternization of the monomer or of a polymer with one of said quaternizing agents can be carried out by conventional methods.
Preferred quaternizing agents are methyl chloride, dimethyl sulfate and diethyl sulfate.
Preferred examples of monomers (a) are 3-methyl-1-vinylimidazolium chloride and m

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