Carbazole derivatives and their use in cosmetics

Details Carbazole derivatives and their use in cosmetics Carbazole derivatives and their use in cosmetics

1995-01-10

1996-08-06

Haley, Jacqueline

Drug, bio-affecting and body treating compositions

Manicure or pedicure compositions

514880, 514881, 514844, 424 62, 424 63, 424 64, 548416, 548418, C07D20980, A61K 700

Patent

active

055434363

DESCRIPTION:

BRIEF SUMMARY
This application is a National Stage Application of PCT/FR94/00549 filed May 10, 1994 and published as WO94/26711 on Nov. 24, 1994.
The present invention relates to novel carbazole derivatives and to a process for their preparation, as well as to their use in cosmetics, the cosmetic compositions containing them and the cosmetic treatment processes using them.
In the cosmetics field, and in particular for make-up compositions such as foundation compositions, tinted creams, mascaras, blushers and eye shadows, lipsticks and nail varnishes, pigments are being sought which are capable of imparting to these various types of products a varied palette of colorations which are reproducible over time and are insoluble in most of the cosmetic media used such as water and cosmetically acceptable solvents. These pigments should, moreover, be stable at the pHs usually used or encountered in the cosmetics field.
Carbazole derivatives are known in the state of the art, these being products of addition of indole compounds with quinones, such as the product of addition of 1,4-naphthoquinone with 1-methyl-5,6-dihydroxyindole, which leads to 2,3-dihydroxy-5-methyldinaphtho-[2,3-a:2',3'-c]carbazole-6,11,12,17-tetron e described in the articles from PROTA (Tetrahedron Letters, Vol. 43, No. 12 pages 2749-54, 1987 and Gazetta Chemica Italiana, 119, 1989), or alternatively the product of addition of 1,4-naphthoquinone with indole, which leads to 5-H-dinaphtho[2,3-a:2', 3'-c]carbazole-6,11,12,17-tetrone described in the article from PROTA (Gazetta Chemica Italiana, 119, 1989) and in the article from PRASAD (Tetrahedron letters, No. 15, pages 1361-1362, 1974).
The Applicant has just discovered novel carbazole derivatives whose use as pigments is particularly advantageous in the cosmetics field, and in particular their use in make-up compositions, especially foundations, tinted creams, mascaras, blushers and eye shadows, lipsticks, nail varnishes and nonpermanent dyeing compositions for the hair. These pigments enable a very varied palette of colorations, which are very much sought after in the cosmetics field and are reproducible, to be obtained, ranging from yellow to brown and including orange-yellow, orange and bright red. In addition, they are stable at pHs between 6 and 8 and are insoluble in most cosmetic media.
In addition, the high crystallinity of these pigments prevents the phenomenon of the colors separating out in the formulations.
One subject of the invention consists of novel carbazole derivatives and the synthesis thereof.
The subject of the invention is also the use of these pigments in cosmetic compositions.
Another subject of the invention consists of the cosmetic compositions containing this pigment, as well as their application for the cosmetic treatment and/or the coloration of keratinous substances such as the skin, the nails the eyelashes, the eyebrows and the hair.
Other subjects of the invention will become apparent on reading the description and the examples which follow.
The novel compounds in accordance with the present invention correspond to the formula (I) ##STR4## in which, R.sub.1 represents a hydrogen atom, a benzyl radical, or a C.sub.1 -C.sub.16 alkyl radical which may or may not be branched and may or may not be saturated; acetyl, nitrile or ##STR5## radical, or a hydrogen atom, it not being possible, however, for R.sub.2 and R.sub.3 simultaneously to represent a hydrogen atom, or R.sub.2 and R.sub.3 form the following ring systems: ##STR6## R.sub.4 represents a hydrogen atom, the methoxy, nitrile or nitro radical or a chlorine atom; hydrogen atom or the methoxy radical; least one of R.sub.1, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 does not denote a hydrogen atom.
The particularly preferred compounds are chosen from: -nitro-10,13-dimethoxy-5H-dinaphtho[2,3-a:2',3'-c]carbazole-6,11,12,17-tet rone, one, one, rone.
The compounds of formula (I) in accordance with the present invention may be obtained by two different preparation processes.
1) The compounds of formula (I) in which R.sub.2 and R

REFERENCES:
Napolitano, A. et al. "A Reinvestigation of the Reactions Between 5,6-Dihydroxyindoles and Quinones" Tetrahedron, vol. 43 No. 12, pp. 2749-2754. (1987).
Prasad, "A reinvestigation of the reaction of indole with 1,4-quinones ", Tetrahedron Letters, No. 15, 1974, pp. 1361-1362.

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