Indoline-based products, processes for preparing them and their

Details Indoline-based products, processes for preparing them and their Indoline-based products, processes for preparing them and their

1993-12-29

1996-12-10

Haley, Jacqueline

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548460, 548490, 548491, 424 59, 424 61, 424 62, 424 63, 424401, A61K 713, C07D20910

Patent

active

055832342

DESCRIPTION:

BRIEF SUMMARY
This application is a National Stage application of PCT/FR93/00030 filed 13 Jan. 1993 and published as WO 93/13744 on 22 Jul. 1993.
The present invention relates to indoline-based products, to processes for preparing them, to their use in cosmetics and to cosmetic compositions employing them.
The use of colored pigments is of very great importance in the cosmetic field, in particular in makeup products intended for making up the exoskeleton and/or the skin.
Inorganic pigments or pigments derived from synthetic direct dyes, or from pure carbon in the case of black pigments, are generally used. These different products present, depending on the application, problems of use, and are not always problem-free from the standpoint of compatibility and toxicology.
The Applicant has discovered new products which can be used as pigments, especially in cosmetics, which are indoline-based products that are especially advantageous in respect of the colorations which they make it possible to obtain, as well as in their cosmetic use.
The products according to the invention are obtained by an oxidative polymerization process employing at least one indoline.
By analogy and for simplification, the term "indoline-based product" or "indoline-based polymer" will be used to denote the product obtained by oxidative polymerization of different compounds containing at least one indoline.
The subject of the present invention is hence new indoline-based products as defined below.
Another subject of the invention consists of the process for preparing these products.
The subject of the invention is also the cosmetic application of these indoline-based products, in particular the products for making up the skin and/or the exoskeleton and for protecting the human epidermis against UV radiation.
Other subjects of the invention will become apparent on reading the description and the examples which follow.
The indoline-based products according to the invention result from the oxidative polymerization of at least one indoline compound corresponding to the formula: ##STR2## in which:
R.sub.1 and R.sub.3 represent, independently of one another, a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group;
R.sub.2 represents a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group or a carboxyl or (C.sub.1 -C.sub.4 alkoxy)carbonyl group;
R.sub.4 denotes a hydrogen atom or a C.sub.1 -C.sub.4 alkyl, hydroxyl, (C.sub.1 -C.sub.4 alkoxy), amino or C.sub.1 -C.sub.10 alkylamino or halogen group;
R.sub.5 denotes a hydrogen atom or a hydroxyl, C.sub.1 -C.sub.4 alkoxy or amino group;
on condition that at least one of the radicals R.sub.4 or R.sub.5 denotes a hydroxyl, alkoxy or amino group; and with the proviso that when R.sub.5 denotes an amino group, R.sub.4 cannot denote an alkylamino radical;
R.sub.4 and R.sub.5 can also form a C.sub.1 -C.sub.2 alkylenedioxy ring, and are at positions 5 and 6;
as well as the corresponding salts.
Among the compounds corresponding to the formula (I), the preferred compounds used according to the invention are chosen from 5,6-dihydroxyindoline, 6-hydroxyindoline, 5,6-methylenedioxyindoline, 7-methoxy-6-hydroxyindoline, 6,7-dihydroxyindoline, 5-hydroxy-4-methoxyindoline, 4,5-dihydroxyindoline, 5-methoxy-6-hydroxyindoline, 4-hydroxy-5-methoxyindoline, 5-hydroxy-6-methoxyindoline, 4,7-dihydroxyindoline, 6-aminoindoline, N-ethyl-4-hydroxyindoline, 1-ethyl-6-amino-indoline, 5,6-diaminoindoline, 1-methyl-6-aminoindoline, 2-methyl-6-aminoindoline, 3-methyl-6-aminoindoline, 2-methyl-5,6-diaminoindoline, 5-chloro-7-aminoindoline, 3-methyl-5,7-diaminoindoline, 5,7-diaminoindoline, 2-methyl-5,7-diaminoindoline, 7-aminoindoline, 2-methyl-7-aminoindoline, 4-aminoindoline, 4-amino-6-chloroindoline, 4-amino-6-iodoindoline, 4-amino-5-bromoindoline, 4-amino-5-hydroxyindoline, 4-amino-7-hydroxyindoline, 4-amino-5-methoxyindoline, 4-amino-7-methoxyindoline, 5-aminoindoline, 2,3-dimethyl-5-aminoindoline, 1-methyl-5-aminoindoline, 2-methyl-5-aminoindoline, 5-[N-(1-methylhexyl)amino]indoline, 5,6-dimethoxyindoline and 5,6-dihydroxy-2-carboxyindoline.
In the com

REFERENCES:
patent: 4013404 (1977-03-01), Parent et al.

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