Skin-conditioning succinic acid derivatives

Details Skin-conditioning succinic acid derivatives Skin-conditioning succinic acid derivatives

1995-05-11

1997-07-22

Venkat, Jyothsna

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Cosmetic, antiperspirant, dentifrice

424 43, 424 59, 424101, 514844, 514937, 514938, 560198, 560199, A61K 748

Patent

active

056501587

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

1. Field of the Invention
This invention relates to new succinic acid derivatives with a lipid-like structure which are suitable as a skin-moisture-regulating component in cosmetic and dermatological preparations.
Keeping the skin healthy and promoting a cosmetically attractive smooth appearance and a soft feel means, above all, maintaining the natural moisture content of the stratum corneum. There are many known skin-moisturizing and moisture-retaining additives for cosmetic and therapeutic skin treatment compositions. They are generally water-soluble or water-binding substances or even hygroscopic compounds. Most of these substances have the disadvantage that, in the event of frequent use, they contribute towards even greater drying out of the skin.
Paraffin oils, triglyceride oils and waxes are distinguished by an excessively occlusive effect which seriously inhibits the transepidermal exchange of water.
2. Discussion of Related Art
The stratum corneum lipids of the human skin and also synthetic analogs of these lipids have recently become known for their effectiveness in regulating skin moisture (J. Soc. Cosmet. Chem. 40 (1989), 273-285). The synthetic lipid analogs in question are, for example, N-acyl sphingosines and fatty acid amides of 1-N-hydroxy-ethylamino-2-hydroxy-3-alkoxypropane (cf. for example EP 0 277 641, EP 0 455 429).


DESCRIPTION OF THE INVENTION

It has now been found that alkyl and alkenyl succinic acid monoester alkoxylates, which are easy to synthesize, are also analogous in their effect to the natural and synthetic ceramides.
The present invention relates to succinic acid derivatives corresponding to formula I: H.sub.2n O).sub.y OR.sup.4 (I) hydroxyalkenyl group containing 6 to 22 carbon atoms, one of the substituents R.sup.2 and R.sup.3 is hydrogen and the other is an alkyl or alkenyl group containing 12 to 22 carbon atoms, n=2 or 3, x and y are average degrees of alkoxylation and have values of 0 to 20 and 1 to 20, respectively, and R.sup.4 is hydrogen or a group R.sup.1 O--(C.sub.n H.sub.2n O).sub.x --CO--CHR.sup.2 --CHR.sup.3 --CO-- or has the same meaning as R.sup.1.
The succinic acid derivatives according to the invention are eminently suitable for use as a skin-moisture-regulating component for the production of cosmetic or therapeutic skin treatment preparations. By virtue of their lipid character, they increase the smoothness and softness of the skin and regulate the transepidermal loss of water without forming a water-impermeable barrier. They prevent the skin from drying out under the effect of climate and surfactants and contribute towards the skin retaining a smooth and youthful appearance.
The succinic acid derivatives according to the invention are prepared by methods known per se in preparative chemistry from the known alkenyl succinic anhydrides which can be obtained by ene addition of maleic anhydride onto olefins. A corresponding succinic anhydride of general formula II: ##STR1## in which one of the substituents R.sup.2 and R.sup.3 is hydrogen and the other is an alkenyl group containing 12 to 22 carbon atoms, is reacted with an alcohol of the formula R.sup.1 --OH to form the monoester and the monoester is then alkoxylated with (x+y) moles of ethylene oxide (n=2) or propylene oxide (n=3). R.sup.1, R.sup.2, R.sup.3, n, x and y have the same meanings as in formula I. If the substituent R.sup.2 or R.sup.3 is to be an alkyl group, the succinic anhydride corresponding to formula II, the monoester or the alkoxylate may be hydrogenated to saturate the double bonds present.
Suitable alcohols R.sup.1 OH are, for example, fatty alcohols containing 6 to 22 carbon atoms, preferably for example stearyl, arachidyl, behenyl, oleyl, linoleyl and erucic alcohol. Alkanediols and alkanetriols containing 6 to 22 carbon atoms, for example ricinolyl alcohol, 9-hydroxystearyl alcohol, and alkanetriols, such as 9,10-dihydroxystearyl alcohol for example, are also suitable.
The alkoxylation of the monoester is preferably carried out in the presence of basic c

REFERENCES:
patent: 3968310 (1976-07-01), Stowell
J. Soc. Cosmet. Chem. 40 (1989), 273-285.

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