Cosmetic composition comprising a compound such as indigoid

Details Cosmetic composition comprising a compound such as indigoid Cosmetic composition comprising a compound such as indigoid

2000-06-13

2002-06-18

Dees, Jose′ G. (Department: 1616)

Drug, bio-affecting and body treating compositions

Live hair or scalp treating compositions

C424S401000, C424S059000, C424S061000, C424S064000

Reexamination Certificate

active

06406685

ABSTRACT:

The present invention relates to the use in cosmetics of compounds of indigoid type, in particular for contributing colour to cosmetic compositions.
Cosmetic compositions and in particular make-up compositions, such as loose or compact powders, foundations, face powders, eyeshadows, lipsticks or nail varnishes, are composed of an appropriate vehicle and of various colouring agents intended to confer a certain colour on the said compositions before and/or after their application to the skin, mucous membranes and/or superficial body growths, such as the nails, eyelashes or hair.
A fairly limited range of colouring agents is used today to create colours, among which colouring agents may be mentioned compounds which are generally insoluble in aqueous and organic media, such as organic lakes, inorganic pigments or pearlescent pigments.
The pigments and lakes used in the make-up field are highly varied in origin and in chemical nature. Their physicochemical properties, in particular particle size, specific surface, relative density and the like, are therefore very different. These differences are reflected by variations in behaviour: their ease of use or dispersion in tie medium, their stability with regard to light or to temperature, and their mechanical properties.
Thus, inorganic pigments, in particular inorganic oxides, such as iron oxides, are very stable with regard to light and pH but give rather lifeless, dull and pale colours. It is therefore necessary to introduce a large amount of them into the cosmetic formulations in order to obtain a sufficiently saturated feature. This high percentage of inorganic particles can, nevertheless, affect the gloss of the composition.
Use may also be made, in order to obtain coloured effects, of pearlescent pigments of varied but never very intense colours, which make it possible to obtain iridescent but mostly fairly weak effects.
In the field of temporary or transient hair colouring, which gives rise to a slight modification of the natural colour of the hair which lasts from one shampooing to another and which serves to beautify or correct a shade which has already been obtained, provision has already been made for colouring with conventional inorganic pigments, in order to introduce a temporary highlight to the hair, but the shades obtained by this colouring remain fairly lifeless, too uniform and not very playful.
In the field of make-up, only organic lakes have until now made it possible to obtain vivid and intense colours. However, most organic lakes exhibit very poor hold with regard to light, which results in a very marked attenuation in their colour over time. They can also be unstable with regard to temperature and/or pH. Furthermore, some lakes result in an excessive degree of bleeding, that is to say that they exhibit the disadvantage of staining the support to which they are applied. Thus, this can have the consequence of staining ocular lenses, in the case of eyeliners or mascaras, or of leaving a colouring on the skin or nails after the removal of make-up, in the case of lipsticks or nail varnishes. Finally, the instability of lakes is further exacerbated when they are used in combination with photoreactive pigments, such as titanium dioxide. In point of fact, these pigments are very widely used in make-up, in particular for protection against UV radiation. Consequently, the use of organic lakes in cosmetics is fairly limited, the consequence of which is a limitation in the tints achievable.
Thus, the need remains to have available colouring agents which can be used in cosmetics and which make it possible to obtain an appropriate colouring of the compositions and of the make-up film obtained, it being necessary for the said colouring agents not to bleed onto the support on which the said compositions are deposited.
After much research, the Applicant Company has demonstrated that the use of a very specific family of organic compounds makes it possible to obtain such a result.
Thus, a subject-matter of the invention is a cosmetic composition comprising, in a cosmetically acceptable medium, at least one compound of formula (I):
in which
R
1
and R′
1
are, independently of one another, saturated or unsaturated, linear, branched or cyclic alkyl radicals having 1 to 18 carbon atoms which are optionally substituted by one or more halogens and/or by one or more hydroxyl radicals and/or interrupted by one or more heteroatoms;
R
2
, R′
2
, R
3
, R′
3
, R
4
, R′
4
, R
5
and R′
5
are, independently of one another, chosen from a hydrogen atom, a halogenated radical, a hydroxyl radical or a saturated or unsaturated, linear or branched, alkyl, alkyloxy, acyl or acyloxy radical having 1 to 6 carbon atoms.
Another subject-matter of the invention is the use of at least one compound of formula (I) for at least partially coating substrate particles.
Another subject-matter of the invention is a pulverulent material composed of substrate particles which are at least partially coated with at least one compound (I).
Yet another subject-matter of the invention is the use of at least one compound of formula (I) and/or of at least one pulverulent material as defined above as colouring agent, in particular in a cosmetic composition.
Another subject-matter of the invention is a cosmetic composition comprising, in a cosmetically acceptable medium, at least one pulverulent material as defined above.
The compounds used in the context of the invention are, in some cases, compounds known in the literature. Some have been disclosed in particular in the publication “2,2′-Binaphthyliden-1,1′-dione, Farbe und Struktur” [2,2′-Binaphthylidene-1,1′-dione, Colour and Structure] by Göltner et al., Liebigs Ann. Chem., 1991, pages 1085-1089. This publication discloses in particular a preparation process which makes it possible to obtain some of these compounds in the form of crystals with a mauve colour or blue colour ranging from pale blue to dark blue.
However, there is nothing in this publication which allows it to be envisaged that these compounds can be employed with success in cosmetic compositions, that is to say that they make possible the preparation of a cosmetically acceptable composition capable of being applied to the skin, the said composition not bleeding.
It is to the credit of the Applicant Company to have found that such a use is possible.
It has also been found that, in addition, it is possible to adjust the colour of the compounds of formula (I) by varying the nature and/or the position of the various R substituents present on the molecule.
It is thus possible to obtain compounds with a colour which can vary from mauve to red, passing through blue and green.
Furthermore, the compounds used in the context of the invention exhibit good stability with regard to temperature, pH and light.
They are also readily accessible by chemical synthesis, even on an industrial scale.
The compounds used according to the invention therefore have the following formula (I):
in which
R
1
and R′
1
are, independently of one another, saturated or unsaturated, linear, branched or cyclic alkyl radicals having 1 to 18 carbon atoms which are optionally substituted by one or more halogens and/or by one or more hydroxyl radicals and/or interrupted by one or more heteroatoms;
R
2
, R′
2
, R
3
, R′
3
, R
4
, R′
4
, R
5
and R′
5
are, independently of one another, chosen from a hydrogen atom, a halogenated radical, a hydroxyl radical or a saturated or unsaturated, linear or branched, alkyl, alkyloxy, acyl or acyloxy radical having 1 to 6 carbon atoms.
Mention may be made, among the heteroatoms, of the oxygen, silicon, nitrogen or sulphur atoms (O, Si, N or S).
R
1
and/or R′
1
are preferably alkyl radicals having 1 to 8 carbon atoms and in particular methyl, CA ethyl, propyl, isopropyl, butyl, pentyl or hexyl radicals. R
1
and R′
1
preferably represent the same radical.
R
2
to R
5
and R′
2
to R′
5
preferably represent a hydrogen atom.
In particular, m

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