Copolymers of carboxylic acids and multiply olefinically unsatur

Details Copolymers of carboxylic acids and multiply olefinically unsatur Copolymers of carboxylic acids and multiply olefinically unsatur

1998-06-02

2000-01-18

Acquah, Samuel A.

Drug, bio-affecting and body treating compositions

Solid synthetic organic polymer as designated organic active...

528271, 528272, 528274, 528302, 528303, 528305, 528306, 524599, 524601, 523500, 522 1, 522 6, 424 7812, 424 782, 424 7833, A61K 3174, C08L 6700, C08G 6300

Patent

active

060155515

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to novel copolymers of carboxylic acids and polyolefinically unsaturated derivatives of the general formula I, with or without one or more copolymerizable monomers. The present invention furthermore relates to the use of these copolymers as thickeners or dispersants, in particular in cosmetic preparations, and to pharmaceutical and, in particular, cosmetic preparations comprising these copolymers.
Conventionally employed as thickeners or viscosity regulators are copolymers of olefinically unsaturated carboxylic acids such as (meth)acrylic acid, maleic acid or maleic anhydride, hydrophobic comonomers such as esters of (meth)acrylic acid and small amounts of a crosslinker, ie. a compound with at least two olefinically unsaturated groups in the molecule. Copolymers of these types are described, for example, in EP-A 328 725 and EP-A 435 066.
In order to achieve an adequate thickening effect, it is necessary for crosslinking to take place during the polymerization. However, control of the crosslinking entails problems with the crosslinker components conventionally employed, for example divinylbenzene, pentaerythritol triallyl ether, diallyltartaramide, bisacrylamidoacetic acid, methylenebisacrylamide, allyl methacrylate, trimethylolpropane diallyl ether or allyl ethers of sucrose. Because of the high double-bond density, many of these compounds are very reactive and therefore form an additional safety risk, and are difficult to store and have an increased skin-irritant potential. In addition, this makes the crosslinking generally take place in a very heterogeneous fashion so that the polymers still contain relatively large amounts of uncrosslinked portions. Because of the high reactivity of the crosslinkers, in general only small amounts of the crosslinking component are used, and even small variations in the crosslinker concentration, as occur in production processes, therefore lead to marked variations in the thickening effect of the copolymers.
It is an object of the present invention to provide a polymer which can be employed as thickener or dispersant and whose thickening effect can be controlled better.
We have found that this object is achieved by a copolymer which is obtainable by free-radical polymerization of -monocarboxylic acid, of an olefinically unsaturated C.sub.4 -C.sub.8 -dicarboxylic acid or of its anhydride or of a mixture of such carboxylic acids or carboxylic anhydrides with derivatives of the general formula I ##STR2## where Z is a vinyl or allyl group or the structure ##STR3## R.sup.1, R.sup.2 are identical or different and are hydrogen or methyl, R.sup.3 is hydrogen, methyl or ethyl, -alkenyl or -cycloalkenyl radical with 5 to 8 carbon atoms in the ring or a mono- or diolefinically unsaturated arylalkenyl radical with a total of 9 to 15 carbon atoms,
In a preferred embodiment, the copolymer according to the invention is composed of acid component A, polyolefinically unsaturated derivative I and copolymerizable monomers.
Particularly suitable as component A are acrylic acid, methacrylic acid or maleic anhydride, but also, in addition, crotonic acid, 2-pentenoic acid, maleic acid, fumaric acid or itaconic acid.
The radical R.sup.1 in the derivatives I is hydrogen or methyl.
The radical R.sup.2 in the derivatives I is preferably hydrogen.
The radical R.sup.3 in the derivatives I is hydrogen, methyl or ethyl, preferably hydrogen or methyl.
The variable X in the derivatives I is preferably oxygen.
The variable Y in the derivatives I is oxygen, NH or N-alkyl. Suitable and preferred as N-alkyl radicals are C.sub.1 -C.sub.4 -alkyl radicals such as methyl, ethyl, propyl, i-propyl, butyl, i-butyl and t-butyl. Y is particularly preferably oxygen and NH, very particularly preferably oxygen.
The degree of alkoxylation or alkimination n is preferably 0 to 20, in particular 0 to 7, very particularly preferably 0 or 1.
The radical R.sup.4 in the derivatives I is a mono- or polyolefinically unsaturated C.sub.6 -C.sub.30 -alkenyl or -cycloalkenyl radical with 5 to 8 carbon at

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