FR2845899A1 - Cosmetic composition containing oil phase and naphthopyran photochromic dye, useful e.g. as make up, provides rapid and reversible color change on exposure to sunlight - Google Patents

Abstract

Cosmetic composition (A) comprises, in a suitable medium, at least one oil phase (OP) and at least one naphthopyran (B), soluble in OP. Cosmetic composition (A) comprises, in a suitable medium, at least one oil phase (OP) and at least one naphthopyran (B), of formulae (I) or (II), soluble in OP. R1 = hydrogen or a substituent; R5 and R6 = saturated or unsaturated cyclic aminoaryl groups, indolinoaryl groups, or a 1-30, best 3-12, C hydrocarbyl group (Hy), linear, branched, cyclic, saturated or unsaturated, optionally containing 1-5 heteroatoms (nitrogen, oxygen, sulfur, silicon or phosphorus), particularly phenyl substituted by CONR2R3, NR2R3 or OR4; R7, R1' and R2' = hydrogen or substituents; R2 and R3 = Hy or together they complete a heterocycle containing 3-10, preferably 4-6 C atoms and optionally 1-5 additional heteroatoms, and optionally substituted by Hy; and R4 = Hy, optionally (per)halogenated, preferably by fluoro, bromo and/or chloro. The full definitions are given in the DEFINITIONS (Full Definitions) Field.

Description

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The present invention relates to novel cosmetic compositions, and in particular new make-up compositions, comprising organic dyes, in particular photochromic dyes.

Makeup compositions, such as free or compact powders, foundations, blushers, eyeshadows or lipsticks, generally consist of a suitable vehicle and one or more coloring agents intended to impart a certain color to said compositions before and / or after their application to the skin, mucous membranes, semi-mucous membranes and / or integuments such as fingernails or hair.

In order to create colors, a fairly limited range of coloring agents is used today, including lacquers, mineral pigments, organic pigments and pearlescent pigments. Lacquers provide bright colors, but most are unstable in light, temperature or pH. Some also have the disadvantage of staining the skin unsightly after application, disgorging the dye. The mineral pigments, in particular the mineral oxides are on the contrary very stable but give colors rather dull and pale. The pearlescent pigments meanwhile allow to obtain varied but not very intense colors, which lead to iridescent effects but usually quite weak.

In the field of temporary or fugitive hair coloring, which gives rise to a slight change in the natural color of the hair which holds from one shampoo to another and which serves to embellish or correct a shade already obtained, it has already been proposed a coloration with usual pigments to bring a temporary reflection to the hair, but the shades obtained by this coloration remain quite dull, too uniform and not very playful. In particular, such a coloration can be assimilated to a "make-up" of the hair.

Recently, it has also been proposed to use photochromic compounds in makeup or hair compositions, so as to obtain pleasant, playful and variable changes in the 'color rendition' of make-up of the skin and / or the hair.

Photochromic compounds are compounds that have the property of changing color when irradiated by a light source, then returning to their original color, or a similar color, when irradiation is stopped. Such compounds find particularly interesting application in cosmetic compositions, in particular in make-up compositions such as foundations, blushers, eyeshadows and lipsticks. Indeed, it has been found that the 'rendering Makeup of a masked skin is different depending on whether one is in natural lighting or artificial lighting. Thus, a make-up made in artificial lighting will appear brighter in natural light. Conversely, a makeup done outdoors will appear darker in an artificially lit place.

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To overcome this problem, it has been proposed, for example by the patent EP359909, cosmetic compositions comprising particular mineral photochromic compounds selected from metal oxides, their hydrates and their complexes. In particular, this document mentions the use of titanium oxide treated so as to make it photochromic, in makeup compositions such as powders and foundations.

However, it has been found that these inorganic photochromic compounds, although they make it possible to obtain a makeup that seems to remain of constant color whatever the lighting, do not however make it possible to obtain a true change in the color of the makeup, or, in other words, a real change in 'makeup rendering'.

On the other hand, it was also found that after stopping the light irradiation, the color of the makeup did not always return in a way acceptable to its initial color, in particular that it did not return completely to a color identical to said initial color and / or not fast enough.

It has also been proposed to use organic photochromic compounds, such as compounds of the spiropyran family or naphthoxoxazines.

These photochromic compounds are particularly interesting insofar as they make it possible to obtain a rapid color change of the support to which they are applied, when said support is exposed to UV for example, with a rapid return to the initial color when the exposure UV stops. One can thus cite the patent FR1604929 which describes cosmetic compositions in particular capillaries in aerosol form, which contain phototropic compounds such as nitrobenzylpyridines, thiosemicarbazones or derivatives of spiropyrans. After spraying these compositions on the hair and exposure to sunlight, we obtain a blue-violet color that becomes pale yellow in the dark.

Also known from EP970689 is a cosmetic make-up product comprising first and second compositions packaged separately, the first composition containing a photochromic coloring agent capable of producing at least one color in the presence of UV and the second composition containing at least one UV filter. . However, the dynamics of these compositions is low: in particular, the return to the initial state is slow.

Also known from the application W002 / 078665, a cosmetic composition comprising liquid dyestuffs, UV absorbers, naphthopyran type or naphthoxazines, and which are encapsulated in a capsule based on acrylate copolymers, and which can be used in the purpose of absorbing UV. However, there is no mention of any photochromic properties of these compositions or dyestuffs.

The object of the present invention is to propose novel cosmetic compositions which have many advantages over those of the prior art, thanks to the use of particular organic dyes.

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Thus, the cosmetic compositions according to the invention make it possible to obtain a makeup capable of rapidly changing color depending on the nature and / or the intensity of the light.

The use of photochromic dyes according to the invention also makes it possible to obtain a clean and pure color makeup, with a 'makeup rendering' which seems more intense.

The color change obtained with these dyes is rapid; it is also reversible and makes it possible to return, after stopping irradiation by a light source, to the initial color, and also in a fast manner.

Moreover, it is thus possible to use, in the cosmetic composition according to the invention, a smaller quantity of photochromic dyes than that generally used in the prior art, for example of the order of 0.01 to 2% in weight, while obtaining a comparable makeup effect and transparency.

In addition, the good cosmetic properties of the compositions according to the invention are maintained.

In addition, although of close chemical structure, the photochromic dyes according to the invention have a wide variety of colors that can go from red to blue through gray, with more or less dark variations. This allows in particular an easier formulation of said dyes, not requiring, for each hue modification, an adaptation of the composition.

In addition, it has surprisingly been found that according to the polarity of the oil or oil mixture forming the oily phase of the cosmetic composition, it is possible to modulate the color of the initial composition before irradiation.

-par-exempte,-du-rose clair au violet-en-passant-parl'orangén-fonctiOTTiJten- évidemment de la nature chimique du colorant, de sa quantité, ainsi que, notamment, de la polarité et de la nature chimique de ladite phase huileuse. Thus, when the oily phase is polar or rather polar, it has, in the presence of photochromic dyes according to the invention, a coloration that can go,

-par-free, from light pink to purple-passing-orangén-functiOTTiJten- obviously the chemical nature of the dye, its quantity, and, in particular, the polarity and the chemical nature of said oily phase.

When the oily phase is rather apolar or weakly polar, it has been found that its color is only slightly or not disturbed by the presence of photochromic dyes before irradiation; the oily phase remains almost colorless.

The photochromic dyes according to the invention are therefore also solvatochromes, that is to say that they change color depending on the nature (polarity) of the solvent in which they are located.

This allows, for example, in particular to obtain a completely colorless photochromic cosmetic product without UV excitation, then a sliced effect (colorless / colored) after irradiation.

In addition, if the composition is pigmented elsewhere, the absence of color provided by the photochromic dye according to the invention makes it possible not to disturb the initial color.

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It is also possible to obtain a light colored photochromic product without UV, which can make it possible to visualize the deposition and to facilitate its application before excitation and intensification of the color.

Thanks to the particular photochromic and solvatochromic dyes according to the invention, it is possible not only to modulate the color conferred by a cosmetic composition comprising said dyes, by irradiation (photochromism) but also to modulate the color of the initial composition, before irradiation.

An object of the present invention is therefore a cosmetic composition comprising, in a cosmetically acceptable medium, at least one oily phase and at least one dye of formula as defined below.

The subject of the invention is also a process for the cosmetic treatment of a support chosen from mucous membranes, semi-mucous membranes, skin and / or integuments, in which a cosmetic composition as defined above is applied to said support; .

In particular, the subject of the invention is a process for the temporary makeup and / or coloring of a support chosen from the mucous membranes, the semi-mucous membranes, the skin and / or the integuments, in which a composition is applied to said support. cosmetic as defined above.

dans lesquelles : * R1 représente : The organic dyes according to the invention are naphthopyrans, and in particular 3H-naphtho- [2,1-b] -pyrans which can be represented by formula (I) or 2H-naphtho- [1,2-b] -pyrannes which can be represented by the formula (II):

in which: R1 represents:

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 - (i) a hydrogen atom; (ii) a hydrocarbon group having 1 to 30, preferably 1-18, and preferably 1 to 12, or even 1 to 6, branched or cyclic linear, saturated or unsaturated, carbon atoms optionally containing 1 to 5 heteroatoms chosen from N, O, S, Si and P, and / or optionally halogenated or perhalogenated, especially by FI, Br and / or Cl; (iii) a hydrocarbon ring formed with one of the bonds "f" or "gh" and the radical R7; or - (iv) a group chosen from -COOR4, -C (O) NR2R3, -NR2R3, -OR4 and SR4, in which: R2 and R3 represent, independently of one another, a hydrocarbon group having 1 to 20, preferably 1-12, and more preferably 1 to 6, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally having 1 to 5 heteroatoms selected from N, O, S, Si and P, taken together with the nitrogen atom to which they are attached form a saturated or unsaturated hydrocarbon heterocycle having 3-10, preferably 4-6, carbon atoms and optionally 1-5 other heteroatoms selected from N, O, S , Si and P, said ring being optionally substituted with at least one hydrocarbon radical having 1 to 20, preferably 1-15, and more preferably 1 to 6, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally containing 1 with 5 heteroatoms selected from N, O, S, Si and P; - R4 represents a hydrocarbon group having 1 to 20, preferably 1-12, and more preferably 1 to 6, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally halogenated or perhalogenated, especially by FI, Br and / or CI, and / or optionally comprising 1 to 5 heteroatoms selected from N, O, S, Si and P; R5 and R6 represent, independently of one another, a group chosen from: - (i) saturated cyclic aminoaryl groups of formula (IIa) or (IIb):

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dans lesquelles le cycle comportant N et X est un cycle saturé qui comprend au total 3 à 30 atomes, de préférence 4-10 et encore mieux 5,6 ou 7 atomes, inclus l'azote, le reste étant des atomes de carbone et/ou des hétéroatomes choisis parmi 0, S, Si, P et/ou des groupements choisis parmi-NH et-NR avec R représentant un radical hydrocarboné ayant 1 à 20, de préférence 1-15, et mieux 1 à 6, atomes de carbone, linéaire, ramifié ou cyclique, saturé ou insaturé, éventuellement comportant 1 à 5 hétéroatomes choisis parmi N, 0, S, Si et P; - (ii) les groupements indolinoaryles de formule (III) :

dans laquelle R10 et R11représentent, indépendamment l'un de l'autre, un groupement choisi parmi (i) les groupements hydrocarbonés ayant 1 à 30, de préférence 1-18, et mieux 1 à 12, voire 1-6, atomes de carbone, linéaires ramifiés ou cycliques, saturés ou insaturés, éventuellement comportant 1 à 5 hétéroatomes choisis parmi N, 0, S, Si et P, et/ou éventuellement halogéné ou perhalogéné, notamment par FI, Br et/ou CI; (ii) les atomes d'halogène, et notamment FI, Br et/ou CI; (iii) les groupements-CN (nitrile), -COOH (carboxylate), -N02 (nitro) ; (iv)

in which the ring containing N and X is a saturated ring which comprises in total 3 to 30 atoms, preferably 4-10 and even more preferably 5 or 7 atoms, including nitrogen, the remainder being carbon atoms and or heteroatoms selected from O, S, Si, P and / or groups selected from -NH and -NR with R representing a hydrocarbon radical having 1 to 20, preferably 1-15, and more preferably 1 to 6, carbon atoms linear, branched or cyclic, saturated or unsaturated, optionally containing 1 to 5 heteroatoms selected from N, O, S, Si and P; - (ii) the indolinoaryl groups of formula (III):

wherein R10 and R11represent, independently of one another, a group selected from (i) hydrocarbon groups having 1 to 30, preferably 1-18, and more preferably 1 to 12, or even 1-6, carbon atoms linear, branched or cyclic, saturated or unsaturated, optionally containing 1 to 5 heteroatoms chosen from N, O, S, Si and P, and / or optionally halogenated or perhalogenated, in particular by FI, Br and / or Cl; (ii) halogen atoms, and especially FI, Br and / or Cl; (iii) CN (nitrile), -COOH (carboxylate), -NO2 (nitro) groups; (Iv)

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dans laquelle m et p sont, indépendamment l'un de l'autre, des entiers allant de 2 à 5; - (iv) les groupements aminoaryles cycliques insaturés de formules (Va), (Vb) ou (Vc) :

a hydrogen atom; a group selected from -C (O) NR 2 R 3, -NR 2 R 3, -OR 4 or -SR 4 with R 2, R 3 and R 4 having the meanings given above; (vi) the radicals R10 and R11 may together form a saturated or unsaturated hydrocarbon ring having a total of 5 to 8 atoms (including the atoms of the indoline ring), said atoms being chosen from C, O, S and / or NR with R representing H or a linear, branched or cyclic, saturated or unsaturated, hydrocarbon radical having 1 to 20 or even 1 to 12 carbon atoms, optionally containing 1 to 5 heteroatoms chosen from N, O, S, Si and P; (iii) the groups of formula (IV):

wherein m and p are, independently of one another, integers ranging from 2 to 5; (iv) unsaturated cyclic aminoaryl groups of formulas (Va), (Vb) or (Vc):

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dans lesquelles R8 et R9, représentent, indépendamment l'un de l'autre, un groupement choisi parmi (i) les groupements hydrocarbonés ayant 1 à 30, de préférence 1-18, et mieux 1 à 12, voire 1-6, atomes de carbone, linéaires ramifiés ou cycliques, saturés ou insaturés, éventuellement comportant 1 à 5 hétéroatomes choisis parmi N, 0, S, Si et P, et/ou éventuellement halogéné ou perhalogéné, notamment par FI, Br et/ou CI; (ii) les atomes d'halogène, et notamment FI, Br et/ou CI; (iii) les groupements-CN (nitrile), -COOH (carboxylate), -N02 (nitro) ; (iv) un atome d'hydrogène ; un groupement choisi parmi -C(O)NR2R3, -NR2R3, - OR4 ou-SR4 avec R2, R3 et R4 ayant les significations données ci-dessus ; - (v) un groupement hydrocarboné ayant 1 à 30, de préférence 2-18, et mieux 3 à 12, atomes de carbone, linéaire, ramifié ou cyclique, saturé ou insaturé, éventuellement comportant 1 à 5 hétéroatomes choisis parmi N, 0, S, Si et P; et notamment un groupement choisi parmi -C6H4-CONR2R3, -C6H4-NR2R3 et C6H4-OR4 avec R2, R3 et R4 ayant les significations données ci-dessus; * R7 représente un groupement choisi parmi : - (i) les groupements hydrocarbonés ayant 1 à 30, de préférence 1-18, et mieux 1 à 12, atomes de carbone, linéaires ramifiés ou cycliques, saturés ou insaturés, éventuellement comportant 1 à 5 hétéroatomes choisis parmi N, 0, S, Si et P, et/ou éventuellement halogéné ou perhalogéné, notamment par FI, Br et/ou CI; - (ii) les atomes d'halogène, et notamment FI, Br et/ou CI; - (iii) les groupements-CN (nitrile), -COOH (carboxylate), -N02 (nitro) ; -N=N- (azo) ; =NH (imino); -CONH2 (amide) ; - (iv) un atome d'hydrogène; - (v) un groupement choisi parmi -C(O)NR2R3, -NR2R3,-OR4 ou-SR4 avec R2, R3 et R4 ayant les significations données ci-dessus; - (vi) le radical R7 pouvant en outre former, avec l'une des liaisons "i", "j", "k", ou "g,h" prises avec le radical R1, ou "f" prise avec le radical R1, un cycle hydrocarboné saturé ayant au total 3 à 8, de préférence 4 à 7, et mieux 5 ou 6, atomes de carbone, éventuellement comportant 1 à 5 hétéroatomes choisis parmi N, 0, S, Si et P;

in which R8 and R9 represent, independently of one another, a group chosen from (i) hydrocarbon groups having 1 to 30, preferably 1-18, and more preferably 1 to 12 or even 1-6, atoms saturated or unsaturated branched or cyclic linear carbon compounds, optionally containing 1 to 5 heteroatoms selected from N, O, S, Si and P, and / or optionally halogenated or perhalogenated, in particular by FI, Br and / or Cl; (ii) halogen atoms, and especially FI, Br and / or Cl; (iii) CN (nitrile), -COOH (carboxylate), -NO2 (nitro) groups; (iv) a hydrogen atom; a group selected from -C (O) NR 2 R 3, -NR 2 R 3, -OR 4 or -SR 4 with R 2, R 3 and R 4 having the meanings given above; (v) a hydrocarbon group having 1 to 30, preferably 2-18, and more preferably 3 to 12, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally containing 1 to 5 heteroatoms chosen from N, 0, S, Si and P; and in particular a group chosen from -C6H4-CONR2R3, -C6H4-NR2R3 and C6H4-OR4 with R2, R3 and R4 having the meanings given above; R7 represents a group chosen from: (i) hydrocarbon groups having 1 to 30, preferably 1-18, and more preferably 1 to 12, carbon atoms, branched or cyclic, saturated or unsaturated, optionally comprising 1 to 5 heteroatoms selected from N, O, S, Si and P, and / or optionally halogenated or perhalogenated, especially by FI, Br and / or Cl; - (ii) the halogen atoms, and in particular FI, Br and / or CI; (iii) CN (nitrile), -COOH (carboxylate), -NO2 (nitro) groups; -N = N- (azo); = NH (imino); -CONH2 (amide); - (iv) a hydrogen atom; (v) a group chosen from -C (O) NR 2 R 3, -NR 2 R 3, -OR 4 or -SR 4 with R 2, R 3 and R 4 having the meanings given above; (vi) the radical R7 may additionally form, with one of the bonds "i", "j", "k", or "g, h" taken with the radical R1, or "f" taken with the radical R1, a saturated hydrocarbon ring having a total of 3 to 8, preferably 4 to 7, and more preferably 5 or 6, carbon atoms, optionally having 1 to 5 heteroatoms selected from N, O, S, Si and P;

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 R'1 represents a group chosen from: - (i) a hydrogen atom; (ii) a hydrocarbon group having 1 to 30, preferably 1-18, and preferably 1 to 12, branched or cyclic linear, saturated or unsaturated carbon atoms, optionally containing 1 to 5 heteroatoms chosen from N, O, S; , Si and P, and / or optionally halogenated or perhalogenated, especially by FI, Br and / or CI; (iii) a group chosen from -C (O) NR 2 R 3, -NR 2 R 3, -OR 4 and -SR 4, with R 2, R 3 and R 4 having the meanings given above; R'2 represents a group chosen from: (i) hydrocarbon groups having 1 to 30, preferably 1-18, and more preferably 1 to 12, branched or cyclic linear, saturated or unsaturated carbon atoms, optionally containing 1 with 5 heteroatoms chosen from N, O, S, Si and P, and / or optionally halogenated or perhalogenated, in particular by FI, Br and / or Cl; - (ii) the halogen atoms, and in particular FI, Br and / or CI; (iii) CN (nitrile), -COOH (carboxylate), -NO2 (nitro) groups; -N = N- (azo); = NH (imino); -CONH2 (amide); - (iv) a hydrogen atom; (v) a group chosen from -C (O) NR 2 R 3, -NR 2 R 3, -OR 4 or -SR 4 with R 2, R 3 and R 4 having the meanings given above.

dans lesquelles R1, R5, R6, R7, R'1 et R'2 sont définis tels que précédemment. Preferably, the organic dyes according to the invention correspond to one of the following formulas (Ia) and (IIa):

in which R1, R5, R6, R7, R'1 and R'2 are defined as above.

 Preferably, R 1 represents a hydrogen atom; a hydrocarbon ring with one of the "f" or "gh" bonds and the radical R7; or a group chosen from -COOR4, -NR2R3, -OR4 and -SR4, in which: R2 and R3 represent, independently of one another, a hydrocarbon group having 1 to 20, preferably 1-12, and better 1-6, atoms of

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 carbon, linear, branched or cyclic, saturated or unsaturated, optionally containing 1 to 5 heteroatoms selected from N, O, S, Si and P, taken together with the nitrogen atom to which they are attached, form a hydrocarbon heterocycle, saturated or unsaturated, having 3-10, preferably 4-6, carbon atoms and optionally 1-5 other heteroatoms selected from N, O, S, Si and P, said ring being optionally substituted by at least one hydrocarbon radical having 1 at 20, preferably 1-15, and more preferably 1 to 6, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally containing 1 to 5 heteroatoms selected from N, O, S, Si and P; R 4 represents a hydrocarbon group having 1 to 20, preferably 1 to 15, and more preferably 1 to 6, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally halogenated or perhalogenated, in particular by FI, Br and / or CI, and / or optionally comprising 1 to 5 heteroatoms selected from N, O, S, Si and P.

dans lesquelles le cycle comportant N et X est un cycle saturé qui comprend au total 3 à 30 atomes, de préférence 4-10 et encore mieux 5, 6 ou 7 atomes, inclus l'azote, le reste étant des atomes de carbone et/ou des hétéroatomes choisis parmi 0, S, Si, P et/ou des groupements choisis parmi-NH et-NR avec R représentant un radical hydrocarboné ayant 1 à 20, de préférence 1-15, et mieux 1 à 6, atomes de carbone, linéaire, ramifié ou cyclique, saturé ou insaturé, éventuellement comportant 1 à 5 hétéroatomes choisis parmi N, 0, S, Si et P; - un groupement hydrocarboné ayant 1 à 30, de préférence 2-18, et mieux 3 à 12, atomes de carbone, linéaire, ramifié ou cyclique, saturé ou insaturé, éventuel- Preferably R5 and R6 represent, independently of one another, a group chosen from: - saturated cyclic aminoaryl groups of formula (IIa) or (IIb):

wherein the ring having N and X is a saturated ring which comprises a total of 3 to 30 atoms, preferably 4-10 and most preferably 5, 6 or 7 atoms, including nitrogen, the balance being carbon atoms and or heteroatoms selected from O, S, Si, P and / or groups selected from -NH and -NR with R representing a hydrocarbon radical having 1 to 20, preferably 1-15, and more preferably 1 to 6, carbon atoms linear, branched or cyclic, saturated or unsaturated, optionally containing 1 to 5 heteroatoms selected from N, O, S, Si and P; a hydrocarbon group having 1 to 30, preferably 2-18, and more preferably 3 to 12, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally

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 1 to 5 heteroatoms selected from N, O, S, Si and P; in particular a group chosen from -C6H4-CONR2R3, -C6H4-NR2R3 and -C6H4-OR4 with R2, R3 and R4 having the meanings given above; Preferably, R7 represents a group chosen from: - (i) hydrocarbon groups having 1 to 30, preferably 1-18, and more preferably 1 to 12, branched or cyclic linear, saturated or unsaturated carbon atoms, optionally containing 1 with 5 heteroatoms chosen from N, O, S, Si and P, and / or optionally halogenated or perhalogenated, in particular by FI, Br and / or Cl; - (ii) the halogen atoms, and in particular FI, Br and / or CI; (iii) CN (nitrile), -COOH (carboxylate), -NO2 (nitro) groups; -N = N- (azo); = NH (imino); -CONH2 (amide); - (iv) a hydrogen atom; (v) a group chosen from -NR 2 R 3, -OR 4 or -SR 4 with R 2, R 3 and R 4 having the meanings given above; (vi) the radical R7 may additionally form, with one of the bonds "i", "j", "k", or "g, h" taken with the radical R1, or "f" taken with the radical R1, a saturated hydrocarbon ring having in total 3 to 8, preferably 4 to 7, and more preferably 5 or 6, carbon atoms, optionally having 1 to 5 heteroatoms selected from N, O, S, Si and P.

Preferably, R '1 represents hydrogen or a hydrocarbon group having 1 to 30, preferably 1-18, and more preferably 1 to 12, carbon atoms, branched or cyclic, saturated or unsaturated, optionally containing 1 to 5 heteroatoms chosen from N, O, S, Si and P, and / or optionally halogenated or perhalogenated, in particular by FI, Br and / or Cl.

Preferably, R'2 represents hydrogen or a group chosen from -NO2, -NR2R3 and -C (O) NR2R3, in which R2 and R3 represent, independently of one another, a hydrocarbon group having 1 to 20, preferably 1-12, and more preferably 1 to 6, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally having 1 to 5 heteroatoms selected from N, O, S, Si and P; taken together with the nitrogen atom to which they are attached, form a saturated or unsaturated hydrocarbon heterocycle having 3-10, preferably 4-6, carbon atoms and optionally 1-5 other heteroatoms selected from N, O, S, Si and P, said ring being optionally substituted with at least one hydrocarbon radical having 1 to 20, preferably 1-15, and more preferably 1 to 6, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally comprising 1 to 5 heteroatoms selected from N, O, S, Si and P.

Mention may more particularly be made of the organic dyes of formula (I) or (la) for which: R1 represents hydrogen; or a group-COOR with R being a radical

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et/ou * R5 et R6 représentent, indépendamment l'un de l'autre, soit (i) un groupement de formule (Ila) :

dans laquelle le cycle comportant N et X est un cycle saturé qui comprend au total 4 à 7 atomes, notamment 5 ou 6 atomes, inclus l'azote, et notamment 3-5 ato- mes de carbone et 0-1 atome d'oxygène ; en particulier un groupement de for- mule:

soit (ii) un groupement hydrocarboné ayant 5 à 14, de préférence 6 à 10 atomes de carbone, linéaire, ramifié ou cyclique, saturé ou insaturé, éventuellement comportant 1 à 2 hétéroatomes choisis parmi N, 0 ou S; en particulier un groupement

dans lesquelles R est un radical hydrocarboné saturé ayant 1 à 12, de préférence 1-6, atomes de carbone, et notamment un radical méthyle ou éthyle; et R2 et R3 sont, indépendamment l'un de l'autre, un groupement hydrocarboné ayant 1 à 20, de préférence 1-15, et mieux 1 à 6, atomes de carbone, linéaire, ramifié ou cycli- saturated hydrocarbon having 1 to 12, preferably 1-6, carbon atoms, and especially a methyl or ethyl radical; or a group

and / or R5 and R6 represent, independently of one another, either (i) a group of formula (IIa):

wherein the ring having N and X is a saturated ring which comprises in total 4 to 7 atoms, especially 5 or 6 atoms, including nitrogen, and especially 3-5 carbon atoms and 0-1 oxygen atom ; in particular a group of formula:

or (ii) a hydrocarbon group having 5 to 14, preferably 6 to 10 carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally comprising 1 to 2 heteroatoms chosen from N, O or S; especially a group

in which R is a saturated hydrocarbon radical having 1 to 12, preferably 1-6, carbon atoms, and especially a methyl or ethyl radical; and R2 and R3 are, independently of one another, a hydrocarbon group having 1 to 20, preferably 1 to 15, and more preferably 1 to 6, carbon atoms, linear, branched or cyclic.

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 saturated or unsaturated, optionally having 1 to 5 heteroatoms selected from N, O, S, Si and P; and / or R7 represents a hydrogen atom or a group -NR2R3, with R2 and R3 representing, independently of one another, a linear or branched, saturated hydrocarbon group having 1 to 12, preferably 1- 6, carbon atoms, and in particular a methyl and / or ethyl group.

dans laquelle le cycle comportant N et X est un cycle saturé qui comprend au total 4 à 7 atomes, notamment 5 à 6 atomes, inclus l'azote, et notamment 4-5 ato- mes de carbone et 0-1 atome d'oxygène ; en particulier un groupement de for- mule:

soit (ii) un groupement hydrocarboné ayant 5 à 14, de préférence 6 à 10 atomes de carbone, linéaire, ramifié ou cyclique, saturé ou insaturé, éventuellement comportant 1 à 2 hétéroatomes choisis parmi N, 0 ou S; Mention may also be made of organic dyes of formula (II) or (IIa) for which: R'1 represents hydrogen or a group-COOR with R being a saturated hydrocarbon radical having 1 to 12, preferably 1-6, carbon atoms, and in particular a methyl or ethyl radical; and / or R5 and R6 represent, independently of one another, either (i) a group of formula (IIa):

wherein the ring having N and X is a saturated ring which comprises in total 4 to 7 atoms, especially 5 to 6 atoms, including nitrogen, and especially 4-5 carbon atoms and 0-1 oxygen atom ; in particular a group of formula:

or (ii) a hydrocarbon group having 5 to 14, preferably 6 to 10 carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally comprising 1 to 2 heteroatoms chosen from N, O or S;

<Desc / Clms Page number 14>

dans lesquelles R est un radical hydrocarboné saturé ayant 1 à 12, de préférence 1-6, atomes de carbone, et notamment un radical méthyle ou éthyle; et R2 et R3 sont, indépendamment l'un de l'autre, un groupement hydrocarboné ayant 1 à 20, de préférence 1-15, et mieux 1 à 6, atomes de carbone, linéaire, ramifié ou cyclique, saturé ou insaturé, éventuellement comportant 1 à 5 hétéroatomes choisis parmi N, 0, S, Si et P; et/ou * R'2 représente l'hydrogène, ou un groupement-NR'R" avec R' et R", identiques ou différents, représentant un groupement hydrocarboné saturé, linéaire ou ramifié, ayant 1 à 12, de préférence 1-6, atomes de carbone, et notamment un groupement méthyle et/ou éthyle; ou un groupement

Parmi ces colorants organiques, on peut citer ceux décrits dans les demandes W094/22850, W098/45281 et WO00/18755. in particular a grouping:

in which R is a saturated hydrocarbon radical having 1 to 12, preferably 1-6, carbon atoms, and especially a methyl or ethyl radical; and R2 and R3 are, independently of one another, a hydrocarbon group having 1 to 20, preferably 1-15, and more preferably 1 to 6, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally having 1 to 5 heteroatoms selected from N, O, S, Si and P; and / or R'2 represents hydrogen, or a group-NR'R "with R 'and R", identical or different, representing a linear or branched, saturated hydrocarbon group having 1 to 12, preferably 1- 6, carbon atoms, and especially a methyl and / or ethyl group; or a group

Among these organic dyes are those described in WO94 / 22850, WO98 / 45281 and WO00 / 18755.

- le 3-phényl-3-(4-morpholinophényl)-6-morpholino-3H-naphto[2,1-b]pyran de formule : Mention may especially be made of the following compounds, more particularly preferred: 3,3-di (4-methoxyphenyl) -6-morpholino-3H-naphtho [2,1-b] pyran of formula:

3-phenyl-3- (4-morpholinophenyl) -6-morpholino-3H-naphtho [2,1-b] pyran of formula:

<Desc / Clms Page number 15>

- le 3-phényl-3-(4-pipéridinophényl)-6-morpholino-3H-naphto[2,1-b]pyran de formule :

le 3-phényl-3-(4-pipéridinophényl)-6-carboxyméthyl-9-N-diméthyl-3Hnaphto[2,1-b]pyran de formule :

le 2-phényl-2-(4-piperidinophényl)-5-carboxyméthyl-9-N-diméthyl-2Hnaphto[1,2-b]pyran de formule :

3-phenyl-3- (4-piperidinophenyl) -6-morpholino-3H-naphtho [2,1-b] pyran of formula:

3-phenyl-3- (4-piperidinophenyl) -6-carboxymethyl-9-N-dimethyl-3H-naphtho [2,1-b] pyran of formula:

2-phenyl-2- (4-piperidinophenyl) -5-carboxymethyl-9-N-dimethyl-2H-naphtho [1,2-b] pyran of formula:

<Desc / Clms Page number 16>

- leurs mélanges.

- their mixtures.

The organic dyes according to the invention are preferably included, alone or as a mixture, in an amount of from 0.001 to 20% by weight, in particular from 0.005 to 10% by weight, preferably from 0.01 to 5% by weight, and even more preferably from 0.05 to 2% by weight, preferably from 0.1 to 1% by weight, relative to the total weight of the cosmetic composition.

Preferably, these organic dyes are photochromic, that is to say that they have a #E greater than or equal to 5, preferably greater than or equal to 10, more preferably greater than or equal to 25, more preferably greater than or equal to 35 or even greater than or equal to 45; AE is measured as defined before the examples.

Advantageously, the organic dyes according to the invention are soluble or possibly dispersible in at least one of the phases of the composition which comprises them.

The composition according to the invention further comprises an oily phase which may comprise one or more cosmetically acceptable oils.

Cosmetically acceptable oil according to the invention is any liquid fatty substance at 25 C, 1 atm, and having a molecular weight of greater than or equal to 160, especially between 170 and 106, or even between 200 and 5 × 10 5, compatible with an application. on the skin, mucous membranes (lips) and / or integuments (nails, eyelashes, eyebrows, hair).

Preferably, the oily phase is macroscopically homogeneous, that is to say homogeneous with the naked eye.

The oily phase may comprise one or more oils, which may be polar or apolar, volatile or non-volatile, and preferably hydrocarbon-based.

By polar oil is meant an oil composed of chemical compounds comprising at least one polar group. The polar groups are well known to those skilled in the art: they may in particular be groups of the alcohol, ester or carboxylic acid type.

<Desc / Clms Page number 17>

In particular, the polar oils according to the invention can be defined as having a mean solubility parameter #a according to the Hansen solubility space, at 25 ° C., of: # a # 5.0 (J / cm 3).

Polar oils include the rather polar oils which have an average solubility parameter at 25 C of: 5.0 #a # 7.0 (J / cm3), and the frankly polar oils which have an average parameter of solubility at 25 ° C of: #a> 7.0 (J / cm3).

In the same way, apolar oils within the meaning of the invention have an average solubility parameter Sa according to the Hansen solubility space, at 25 ° C., of: ## EQU1 ## (J / cm 3).

Apolar oils within the meaning of the invention include frankly apolar oils (Sa = O) and low polar oils which have an average solubility parameter at 25 ° C of: 0 <a <5.0 (J / cm 3).

Thus, the higher the value of #a, the higher the polarity of the oil.

The definition and calculation of the solubility parameters in the HANSEN three-dimensional solubility space are described in the article by C. M. Hansen: "The three dimensional solubility parameters" J. Paint Technol. 39, 105 (1967).

According to this Hansen space: #D characterizes the LONDON dispersion forces resulting from the formation of dipoles induced during molecular shocks; - #p characterizes the DEBYE interaction forces between permanent dipoles as well as the KEESOM interaction forces between induced dipoles and permanent dipoles; - #h characterizes the specific interaction forces (hydrogen bond, acid / base, donor / acceptor type, etc.); - #a is determined by the equation: 8a = (# p2 + # h2) The parameters 8p, 8h, #D and Sa are expressed in (J / cm3).

âdmel = L Xi 80 ; spmel z Xi Ôpi et âhmel = X xi âhi i i Samel =(#2 pmel + #2hmel)1/2 où xi représente la fraction volumique du composé i dans le mélange. When the oily phase is a mixture of different oils, the solubility parameters of the mixture are determined from those of the compounds taken separately, according to the following relationships:

σmel = L Xi 80; ## EQU1 ## where xi represents the volume fraction of compound i in the mixture.

It is within the abilities of those skilled in the art to determine the amounts of each oil to obtain an oily phase satisfying the desired criteria.

According to a first preferred embodiment of the invention, the oily phase is polar and may comprise mainly, or even exclusively, one or more polar oils (rather or substantially polar) in a mixture, which can therefore represent 5 to 100% by weight, including 10-90%, even 15-60% and more

<Desc / Clms Page number 18>

 better 20-50% by weight of the total weight of said oily phase.

According to this first preferred embodiment, the polar oily phase has an average solubility parameter #a according to the Hansen solubility space, at 25 ° C., greater than or equal to 5.0 (J / cm 3), in particular greater than or equal to 5 , 3, even greater than or equal to 5.5 and even better than or equal to 6.0 (J / cm3), or even greater than or equal to 7.0 (J / cm3).

According to a second preferred embodiment of the invention, the oily phase is apolar and may comprise 5 to 100% by weight, in particular 10-90%, even 15-60% and even more preferably 20-50% by weight of a or several apolar oils (apolar or slightly polar); it has a mean solubility parameter #a according to Hansen's solubility space, at 25 ° C., less than 5.0, in particular less than or equal to 4.9, more preferably less than or equal to 4.5, and even better still less or equal to 4.0 (J / cm3).

The oils that may be used in the oily phase may be chosen from, alone or as a mixture, oils of animal, vegetable, mineral or synthetic origin; volatile or not.

The term "volatile oil" means the oils having, at 25 ° C., a vapor pressure of between 0.02 and 300 mmHg (evening 2.66 at 40000 Pa). Preferably, volatile oils are used whose flash point is of the order of 30-100 C.

These include: animal or vegetable oils formed by esters of fatty acids and polyols, in particular liquid triglycerides, for example sunflower, corn, soybean, squash, grape seed oils, sesame, hazelnut, apricot, almonds or avocado; fish oils, tricaprocaprylate glycerol, or vegetable or animal oils of formula RiCOOR2 in which R 1 represents the residue of a higher fatty acid having 7 to 19 carbon atoms and R 2 represents a branched hydrocarbon chain containing from 3 to 20 carbon atoms, for example, Purcellin oil; paraffin oil, petrolatum, calophyllum, macadamia, rapeseed, copra, peanut, palm, castor oil, jojoba, olive or cereal sprouts; shea butter oil ; perhydrosqualene; esters and synthetic ethers, in particular of fatty acids, such as the oils of formula RiCOOR 2 in which R 1 represents the residue of a higher fatty acid comprising from 7 to 29 carbon atoms and R 2 represents a hydrocarbon-based chain containing from 3 to 30 carbon atoms; carbon atoms such as isopropyl myristate, 2-ethylhexyl palmitate, octyl-2-dodecyl stearate, octyl-2-dodecyl erucate, isononyl isononanoate, isostearyl isostearate; hydroxylated esters such as isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, triisocetyl citrate, heptanoates, octanoates, decanoates of fatty alcohols; polyol esters such as propylene glycol dioctanoate, diheptanoate

<Desc / Clms Page number 19>

 neopentyl glycol, diethylene glycol diisononanoate; pentaerythritol esters such as pentaerythritol tetraisostearate; esters of the tridecyl trimellitate type; fatty alcohols having from 12 to 26 carbon atoms, such as octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol and oleyl alcohol.

linear or branched hydrocarbons of mineral or synthetic origin, such as liquid paraffins and their derivatives, petroleum jelly, polydecenes, and hydrogenated polyisobutene such as parleam; isoparaffins such as isohexadecane and isodecane; glycerides and in particular acetylglycerides or triglycerides of fatty acids having 4 to 10 carbon atoms, such as triglycerides of heptanoic, octanoic and capric / caprylic acids.

Particularly preferred polar oils include octyldodecanol, hexyldecanol, octyldecanol, oleic alcohol, castor oil, diisostearyl malate, glyceryl triheptanoate, glyceryl trioctanoate, triglyceride, and the like. capric / caprylic acids, triisononanoïn, tridecyl trimellitate, and mixtures thereof.

Among the particularly preferred apolar oils include aliphatic hydrocarbons including C6-C40 such as paraffin oils, volatile, such as isohexadecane or isododecane, or non-volatile, and derivatives thereof; petroleum jelly, hydrogenated or non-hydrogenated polydecenes, hydrogenated polyisobutene such as Parleam oil, squalane, polybutylenes, isononyl isononanoate; fluorinated oils, especially perfluorinated oils, and mixtures thereof.

The following oils may especially be mentioned:

<Tb>
<tb>#a<SEP> (J / cm3)
<tb> oil <SEP> of <SEP> ricin <SEP> 9.09 <SEP>
<tb> 2-hexyldecanol <SEP> 8.55 <SEP>
<tb> alcohol <SEP> oleic <SEP> 8,17
<tb> Octyldodecanol <SEP> 7.69 <SEP>
<tb> triglyceride <SEP> of <SEP><SEP> heptanoic acid <SEP> 7.29
<tb> diisostearyl malate <SEP> 7.19 <SEP>
<tb> triglyceride <SEP> of <SEP><SEP> octanoic acid <SEP> 6.87 <SEP>
<tb> triglyceride <SEP><SEP> acids <SEP> capric / caprylic acid <SEP> 6.69 <SEP>
<tb> Triisononanoin <SEP> 6.54 <SEP>
<tb> Trimellilate <SEP> of <SEP> tridecylate <SEP> 5.35 <SEP>
<tb> isononyl isononanoate <SEP><SEP> 4.87 <SEP>
<tb> Polyisobutene <SEP> hydrogenated <SEP> 0 <SEP>
<Tb>

Isododécane ~~ ~ I ~ ~~.~~~. ~~~~ ~~~~~~- ~~~. ~~~~~~~1

Isododecane ~~ ~ I ~~~. ~~~. ~~~~ ~~~~~~ - ~~~. ~~~~~~~ 1

<Desc / Clms Page number 20>

 The oily phase is preferably chosen in such a way that the photochromic organic dye (s) are soluble or dispersible therein.

The oily phase is preferably in an amount of 1 to 99% by weight, especially 10 to 90% by weight, preferably 15 to 80% by weight, relative to the total weight of the cosmetic composition.

The composition according to the invention may furthermore comprise other fatty substances than the above oils, which may be chosen by the person skilled in the art on the basis of his general knowledge, so as to give the final composition the desired properties. for example in consistency and / or in texture.

These additional fatty substances may be waxes, gums and / or pasty fatty substances of animal, vegetable, mineral or synthetic origin, and mixtures thereof.

A wax, within the meaning of the present invention, is a lipophilic fat compound, solid at room temperature (25 C), with reversible solid / liquid state change, having a melting point greater than 40 C and up to 200 C, generally a hardness greater than 0.5 MPa, and having in the solid state an anisotropic crystalline organization.

Mention may be made in particular of waxes of animal, vegetable, mineral or synthetic origin, such as microcrystalline waxes, paraffin wax, petrolatum, petroleum jelly, ozokerite, montan wax; beeswax, lanolin wax and its derivatives; Candelilla wax, Ouricury wax, Carnauba wax, Japan wax, cocoa butter, cork fiber or sugar cane wax, lignite wax, rice bran wax, fir wax, cotton wax; hydrogenated oils having a melting point above 40 C (approximately), such as hydrogenated jojoba oil; fatty esters and glycerides concretes at 25 C; polyethylene waxes and waxes obtained by Fischer-Tropsch synthesis; hydrogenated oils that are solid at 25 ° C .; lanolines.

The pasty fatty substances generally have a melting point of between 25 and 60 [deg.] C., preferably between 30 and 45 [deg.] C., and / or a hardness of between 0.001 and 0.5 MPa, preferably between 0.005 and 0.4 MPa. There may be mentioned lanolines and their derivatives, or cholesterol esters.

These additional fatty substances may be present in an amount of 0.1-50% by weight, especially 3-40% by weight, more preferably 5-30% by weight, relative to the total weight of the composition.

The composition according to the invention may be anhydrous, or may also comprise an aqueous phase, which may comprise water, floral water such as blueberry water and / or mineral water such as VITTEL water, the water of LUCAS or the water of LA ROCHE POSAY.

 Said aqueous phase may comprise from 0.1 to 14% by weight, relative to

<Desc / Clms Page number 21>

 total weight of the aqueous phase of a C2-C6 monoalcohol such as ethanol, propanol, butanol, isopropanol and isobutanol.

The composition according to the invention may optionally comprise a surfactant, especially when it is in the form of an emulsion, preferably in an amount of from 0.01 to 30% by weight relative to the total weight of the composition.

The alkali salts, ammonium salts, amine salts or aminoalcohol salts of the following compounds may be mentioned, alone or as a mixture, of the following compounds: alkyl sulphates, alkyl ether sulphates, alkyl sulphates and ether sulphates, alkylaryl polyethersulphates, monoglyceride sulphates , alkylsulphonates, alkylamides sulphonates, alkylaryl sulphonates, a-olefin sulphonates, paraffin sulphonates, alkyl sulphosuccinates, alcoyléthersulfosuccinates, alkylamides sulfosuccinates, alcoylsulfosuccinamates, alcoylsulfoacétates, alcoylpolyglycérol carboxylates, alkyl phosphates / alcoylétherphosphates, acyl sarcosinates, alcoylpolypeptidates, alcoylamidopolypeptidates, acyl isethionates, alcoyllaurates. The alkyl or acyl radical in all these compounds generally refers to a chain of 12 to 18 carbon atoms.

Mention may also be made of soaps and salts of fatty acids such as oleic, ricinoleic, palmitic or stearic acids, coconut oil acids or hydrogenated coconut oil acids and especially amine salts such as stearates. amine; acyl lactylates, the acyl radical of which comprises 8-20 carbon atoms; carboxylic acids of polyglycol ethers.

Mention may also be made of fatty-chain polyethoxylated, polypropoxylated or polyglycerolated alcohols, alkyl phenols and fatty acids containing 8 to 18 carbon atoms; copolymers of ethylene oxide and propylene oxide, condensates of ethylene oxide and propylene oxide on fatty alcohols, polyethoxylated fatty amides, polyethoxylated fatty amines, ethanolamides, fatty acid esters of glycol, esters of fatty acids (stearate, oleate) of sorbitan, oxyethylenated or otherwise, sucrose fatty acid esters, polyethylene glycol fatty acid esters (monostearate or polyethylene glycol monolaurate); phosphoric triesters, fatty acid esters of glucose derivatives; alkylpolyglycosides and alkylamides of amino sugars; the condensation products of an α-diol, a monoalcohol, an alkylphenol, an amide or a diglycolamide with glycidol or a glycidol precursor.

There may also be mentioned trioleyl phosphate; fatty acid esters of polyols such as mono-, di-, tri- or sesquiolates or stearates of sorbitol or glycerol, laurates of glycerol or polyethylene glycol; alkyl or alkoxy dimethicone copolyols having an alkyl or pendant alkoxy chain or a silicone backbone having, for example, from 6 to 22 carbon atoms; polyoxyethylenated alkyl (lauryl, cetyl, stearyl, octyl) ethers and dimethicone copolyols.

The composition according to the invention may also comprise one or more thickening agents, for example in preferential concentrations of 0.01 to 6%

<Desc / Clms Page number 22>

 by weight relative to the total weight of the composition. The thickening agent may be chosen from, alone or as a mixture: polysaccharide biopolymers such as xanthan gum, locust bean gum, guar gum, alginates, modified celluloses such as hydroxyethylcellulose, methylcellulose, hydroxypropylcellulose and carboxymethylcellulose, starch derivatives, cellulose ether derivatives having quaternary ammonium groups, cationic polysaccharides; synthetic polymers such as polyacrylic acids such as glyceryl poly (meth) acrylate polymers such as HISPAGEL or LUBRAGEL from HISPANO QUIMICA or GARDIAN, polyvinylpyrrolidone, polyvinyl alcohol, crosslinked polymers of acrylamide and ammonium acrylate such as PAS 5161 or BOZEPOL C from HOECHST; acrylate / octylacrylamide copolymers such as Dermacryl from National Starch; polyacrylamide-based polymers such as SEPIGEL 305 from SEPPIC, crosslinked polymers of acrylamide and methacryloyloxyethyltrimethylammonium chloride, such as SALCARE SC 92 from ALLIED COLLOIDS, magnesium aluminum silicate; optionally modified clays, such as hectorites modified with a C 10 -C 22 fatty acid ammonium chloride, such as hectorite modified with di-stearyl dimethyl ammonium chloride; - optionally modified silica; galactomannans containing from one to six and better still from two to four hydroxyl groups per sac, substituted with a saturated or unsaturated alkyl chain, such as guar gum alkylated with C1-C6 alkyl chains and better still with C1 to Cs and more particularly ethyl guar having a degree of substitution of 2 to 3 such as that sold by Aqualon under the name N-HANCE-AG; cellulose derivatives such as ethylcellulose.

block copolymers, especially of the "diblock" or "triblock" type of the polystyrene / polyisoprene type, polystyrene / polybutadiene, polystyrene / copoly (ethylenebutylene) or else polystyrene / copoly (ethylenepropylene) such as those sold under the name 'Kraton' by Shell Chemical; polymers of the polyamide type, for example comprising a polymer backbone having amide repeating units, and optionally at least one pendant fatty chain and / or at least one optionally functionalized terminal chain, having from 8 to 120 carbon atoms and being related to these amide units, among which may be mentioned the commercial products sold by Arizona Chemical under the names Uniclear 80 and Uniclear 100 which are a mixture of copolymers of a C36 diacid condensed on ethylene diamine with a weight average molecular weight of about 6000, the terminal ester groups resulting from the esterification of the remaining acid termini with cetyl alcohol, stearyl alcohol or mixtures thereof (also called cetylstearyl alcohol).

<Desc / Clms Page number 23>

Depending on the intended application, the composition may further comprise a film-forming polymer. This is generally the case when it is desired to prepare a composition such as nail polish, mascara, eyeliner or lip lacquer.

The polymers can be dissolved or dispersed in the cosmetically acceptable medium. The polymers may be present at a content ranging from 0.01% to 40% by weight relative to the total weight of the composition.

The composition may also comprise a plasticizer chosen from the usual plasticizers and which may be present at a content ranging from 0.1 to 40% by weight relative to the total weight of the composition.

The composition may further comprise a particulate phase, which may include pigments and / or nacres and / or fillers commonly used in cosmetic compositions.

By pigments, it is necessary to include white or colored particles, mineral or organic, intended to color and / or opacify the composition. By fillers, it is necessary to include colorless or white particles, mineral or synthetic, lamellar or non-lamellar, intended to give the body or rigidity to the composition, and / or softness, dullness and uniformity make-up.

By nacres, it is necessary to understand iridescent particles which reflect the light, in particular produced by some shellfish in their shell or else synthesized.

The pigments may be present in the composition in a proportion of 0.01 to 25% by weight of the final composition, and preferably in a proportion of 3 to 10% by weight.

They can be white or colored, mineral or organic, of usual size or nanometer. They can be in the form of powder or pigment paste. There may be mentioned oxides of titanium, zirconium or cerium, as well as oxides of zinc, iron or chromium, ferric blue, chromium hydrate, carbon black, ultramarines (polysulfides of aluminosilicates) , manganese pyrophosphate and some metal powders such as silver or aluminum. D & C pigments and lacquers commonly used to impart a make-up effect to the lips and the skin, which are salts of calcium, barium, aluminum, strontium or zirconium, may also be mentioned.

 The nacres may be present in the composition in a proportion of 0.01 to 20% by weight, preferably at a rate of the order of 3 to 10% by weight. Among the nacres that can be envisaged, mention may be made of natural mother-of-pearl, mica coated with titanium oxide, with iron oxide, with natural pigment or with bismuth oxychloride, and with colored titanium mica.

 The fillers, which may be present in amounts of 0.01 to 60% by weight, preferably 3 to 10%, in the composition may be inorganic or synthetic, lamellar or non-lamellar. Mention may be made of talc, mica, silica, kaolin, nylon and polyethylene powders, Teflon, starch, boron nitride, polymer microspheres such as Expancel (Nobel Industrie), Polyclap (Dow Corning) and Silicone Resin Microbeads (Toshearl Tospearls

<Desc / Clms Page number 24>

 ba, for example), precipitated calcium carbonate, magnesium carbonate or hydrocarbon, metal soaps derived from organic carboxylic acids having from 8 to 22 carbon atoms.

The composition may further comprise a dye, especially a natural organic dye such as carmine scale, and / or a synthetic dye such as halo-acid, azo, anthraquinone dyes. Mention may also be made of mineral dyes such as copper or iron sulphate. Other examples include Sudan Brown, Sudan Red and Annatto, as well as beet juice, carotene and methylene blue. The dye may be present in the composition, alone or as a mixture, in a proportion of 0.001 to 15% by weight, preferably 0.01 to 5% by weight and especially 0.1 to 2% by weight, relative to to the total weight of the composition.

The composition may further comprise a photochromic compound other than photochromic organic dyes of formula (I) or (II). Mention may in particular be made of mineral photochromic compounds, and more particularly doped alumino-silicates such as halogen-doped sodalite, or metal oxides or hydrates such as titanium oxides made photochromic with the aid of a metal chosen from iron, chromium, copper, nickel, manganese, cobalt, molybdenum, as such or in salt form such as sulfate, chlorate, nitrate, acetate. The photochromic compound can be incorporated in the composition in an amount of 0.001-20% by weight based on the total weight of the composition, preferably in an amount of 0.1-10% by weight.

The composition may further comprise a UV filter which may be incorporated in the composition in an amount of 0.01-20% by weight based on the total weight of the composition, preferably in an amount of 0.1-10% by weight. weight. Among the sunscreens that may be used, there may be mentioned compounds belonging to the para-aminobenzoic families; dessalicylates; dibenzoylmethanes; cinnamates; ss, ss'-diphenylacrylate derivatives; benzophenones; desbenzylidene camphors; phenyl benzimidazoles; triazines; desphenyl benzotriazoles; anthranilics; imidazolines and / or benzalmalonates.

The composition may furthermore comprise any additive usually used in the cosmetics field, such as antioxidants, perfumes, essential oils, preservatives, lipophilic or hydrophilic cosmetic active agents, moisturizers, vitamins, sphingolipids, agents and the like. self-tanning agents such as DHA, optical brighteners, defoamers, sequestering agents.

Of course the person skilled in the art will take care to choose the possible compounds

<Desc / Clms Page number 25>

 and / or the amount thereof, such that the advantageous properties of the composition according to the invention are not, or not substantially, impaired by the addition envisaged.

The composition according to the invention is advantageously photochromic, that is to say that it has an AE greater than or equal to 5, preferably greater than or equal to 10, more preferably greater than or equal to 25, more preferably greater than or equal to 35. or even greater than or equal to 45; AE is measured as defined before the examples.

The cosmetic composition according to the invention finds particular application particularly interesting in the field of makeup of the skin, semi-mucous membranes, mucous membranes and / or integuments (nails, eyelashes, eyebrows, hair and hair).

It may comprise or be in the form of a suspension, especially a dispersion of oil in water by means of vesicles; an oily solution optionally thickened or gelled; an oil-in-water, water-in-oil or multiple emulsion; a gel or a mousse; oily or emulsified gel; a dispersion of vesicles, in particular lipids; a biphase or multiphase lotion; a spray; loose, compact or cast powder; an anhydrous paste. This composition may have the appearance of a lotion, a cream, an ointment, a soft paste, an ointment, a solid cast or molded and especially stick or cup, or compacted solid.

The cosmetic composition according to the invention may be in the form of a care product and / or make-up of the skin of the body or of the face, the lips and the hair, a sun-product or self-tanning product, or even a hair product. It finds particular application in the field of lipsticks, foundations, blushers or eyeshadow, free or compact powders, tinted creams, body makeup products, skin coloring products , eyeliners and mascaras.

The invention is illustrated in more detail in the following examples.

Measurement of AE The measurements of L, a and b were carried out on LENETA brand contrast card and reference FORM 1A PENOPAC, for a composition spread of 50 microns thick.

The reflection measurements were made using a MINOLTA 3700D spectrocolorimeter.

The initial trichromatic coordinates of the composition were thus determined.

<Desc / Clms Page number 26>

 before irradiation (Lo, ao and bo). The composition was then subjected to UV irradiation (flow of 2 mW / cm 2 of UVA radiation) for two minutes and then immediately after stopping irradiation, determined the trichromatic coordinates after irradiation (L, a and b ). Less than 5 seconds elapsed between stopping the irradiation and determining the new coordinates.

We then calculated the AE in the following way: #E = [(L - Lo) 2 + (a - ao) 2 + (b - b0) 2] 1/2 When we measure the AE of a dye and not a composition comprising it, the measurement is carried out on a solution comprising 0.05% by weight of dye in diisostearyl malate. Then the measurement is made as above.

EXAMPLE 1 The AE (before and after UV irradiation for 2 minutes) of different photochromic dyes according to the invention was determined at 1% by weight in a white lipstick base comprising: 2-octyl dodecanol 0.5% - hectorite modified with di-stearyl di-methyl ammonium chloride 0.6% - liquid lanolin 27.2% - microcrystalline wax 10.5% - polyglycerolated beeswax (3 moles) 4.2% - acetylated lanolin 6, 7% - arara oil (oleic acid esters) 13.5% - oxypropylenated lanolin wax (5 op) 6.7% - oleyl erucate 13.5% - oleic-linoleic-linolenic acid triglycerides 1.7% - palmitic-oleic-linoleic acid triglycerides 13.5% - 0.1% sodium hyaluronate - 0.1% preservatives - 0.5% vitamin - 0.7% UV filter A composition is therefore prepared thus comprising 1% of dye according to the invention and 99% of the base above.

The L, a and b measurements were performed on a LENETA brand contrast card and PENOPAC FORM 1A reference, for a composition spread of 50 microns in thickness.

<Desc / Clms Page number 27>

The reflection measurements were made using a MINOLTA 3700D spectrocolorimeter.

The initial trichromatic coordinates of the composition before irradiation (Lo, ao and bo) were thus determined. The compositions were then subjected to UV irradiation (flow of 2 mW / cm 2 of UVA radiation) for two minutes and immediately after stopping irradiation, the trichromatic coordinates after irradiation (L, a and b). Less than 5 seconds elapsed between stopping the irradiation and determining the new coordinates.

We then calculated the AE in the following way: #E = [(L - Lo) 2 + (a - ao) 2 + (b - b0) 2] 1/2 We obtain the following results:

<Tb>
<tb> Colorant <SEP>#E
<Tb>

3,3-di(4-methoxyphenyl)-6-morpholino-3H-naphto[2,1-b]pyran 51 3-phényl-3-(4-morpholinophényl)-6-morpholino-3H- 53

3,3-di (4-methoxyphenyl) -6-morpholino-3H-naphtho [2,1-b] pyran-3-phenyl-3- (4-morpholinophenyl) -6-morpholino-3H-53

<Tb>
<tb> na <SEP> hto <SEP> 2.1-b <SEP> ran <SEP>
<tb> 3-phenyl-3- (4-piperidinophenyl) -6-morpholino-3H-naphtho [2,1- <SEP> 49
<tb> b <SEP> ran <SEP>
<Tb>
A measure of AE greater than about 30 means that the dye gives a bright color; it is found that this is particularly the case with the dyes according to the invention tested here.

EXAMPLE 2 In order to demonstrate the solvatochromism of the dyes according to the invention, ie the influence of the nature of the oil on the color expression of said photochromic dyes, without UV exposure, several simplex mixtures have been prepared. comprising 0.05% by weight of 3-phenyl-3- (4-pyperidinophenyl) -6morpholino-3H-naphtho [2,1-b] pyran (James Robinson Reversacol Ruby) in various oils.

The trichromatic coordinates (Lh, ah and bh) of the oil alone and the oil + dye mixture (Lm, am and bm) were determined and the #E 'calculated as follows: AE' = [(Lh - Lm) 2 + (ah - am) 2 + (bh - bm) 2] 1/2 To do this, a Minolta 3700D spectrocolorimeter was used in transmission mode, with a plastic tank (optical path "walls tank + oil + optionally dye "= 1 cm).

<Desc / Clms Page number 28>

The following results are obtained:

<Tb>
<tb> Oil <SEP>#a<SEP> of <SEP> oil <SEP> only <SEP>#E'<SEP> from <SEP> blend
<tb> (J / cm3) <SEP> oil <SEP> + <SEP> dye
<tb> oil <SEP> of <SEP> ricinus <SEP> 9.09 <SEP> 33.6278
<tb> Octyldodecanol <SEP> 7.69 <SEP> 37.6049
<tb> Diisostearyl malate <SEP> 7.19 <SEP> 12.9041
<tb> triglyceride <SEP><SEP> acids <SEP> 6.69 <SEP> 12.4093
<tb> capric / caprylic
<tb> Triisononanoin <SEP> 6.54 <SEP> 12.8122
<tb> Trimellilate <SEP> of <SEP> tridecylate <SEP> 5.35 <SEP> 14.2178
<tb> isononyl isononanoate <SEP><SEP> 4.87 <SEP> 7.7386
<tb> Hydrogenated Polyisobutene <SEP><SEP> 0 <SEP> 6,6920
<tb> Isododecane <SEP> 0 <SEP> 4.2421
<Tb>
It is therefore found that the solvatochrome effect, namely the change in color by the oil, is all the more important that the oil is polar.

Example 3 The mixtures prepared in Example 2 were irradiated with UV (flow of 2 mW / cm 2 of UVA) for 2 minutes.

The trichromatic coordinates of the mixture were then again determined, as in Example 2, after irradiation (Lm ', am, and bm') and the AE calculated as follows: AE = [(Lm.-Lm) 2 + (am.-am) 2 + (bm, - bm) 2] 1/2 Less than 5 seconds elapsed between stopping irradiation and determining the new coordinates.

The following results are obtained:

<Tb>
<tb> Oil <SEP> AE
<tb> oil <SEP> of <SEP> ricin <SEP> 19.02 <SEP>
<tb> octyldodecanol <SEP> 20.88 <SEP>
<tb> diisostearyl malate <SEP> 38.79 <SEP>
<tb> triglyceride <SEP><SEP> acids <SEP> capric / caprylic acid <SEP> 23,70 <SEP>
<tb> Triisononanoin <SEP> 21.62 <SEP>
<tb> Trimellilate <SEP> of <SEP> tridecylate <SEP> 13,74 <SEP>
<tb> isononyl isononanoate <SEP><SEP> 25.47 <SEP>
<tb> Polyisobutene <SEP> hydrogenated ~~~~~~~~~~~~~~~ 17,69 ~~~~~~
<Tb>

<Desc / Clms Page number 29>

<Tb>
<tb> Isododecane <SEP> 19.17
<Tb>
It is therefore clear that the photochromic effect exists for the dye solubilized in different oils.

Example 4 To the mixtures prepared in Example 2 (oils + 0.05% by weight of Reversacol Ruby dye) was added 15% by weight of polyethylene wax (apolar wax), and then, before and after irradiation, 2 was measured. UV minutes (flux of 2 mW / cm 2 of UVA), the trichromatic coordinates L, a, b on thin films of composition, thickness 50 microns, cast on a contrast map.

For this purpose, a Minolta 3700D spectrocolorimeter was used in reflection mode; less than 5 seconds elapsed between stopping irradiation and determining the new coordinates.

As before, the AE was calculated and the following results are obtained:

<Tb>
<tb> Nature <SEP> of <SEP> oil <SEP> in <SEP><SEP> composition <SEP>#E
<tb> (15% <SEP> of <SEP> wax <SEP> + <SEP> 0.05% <SEP> of <SEP> dye)
<tb> oil <SEP> of <SEP> ricinus <SEP> 26,75
<tb> octyldodecanol <SEP> 31.09
<tb> diisostearyl malate <SEP> 43.12
<tb> Triisononanoin <SEP> 33.70
<tb> Trimellilate <SEP> of <SEP> tridecylate <SEP> 31,98
<tb> Isononanoate <SEP> Isononyl <SEP> 27.74
<tb> Polyisobutene <SEP> hydrogenated <SEP> 18.36
<tb> Isododecane <SEP> 27,21
<Tb>
It can therefore be seen that the photochromic effect always exists in a structured system, that is to say in the presence of a wax.

EXAMPLE 5 An apolar gloss for the lips comprising (% by weight) was prepared: - Reversacol Ruby 0.05% - polybutylene (#a = 0) 99.95% A very light salmon initial color gel is obtained, which becomes salmon sustained after exposure for a few seconds in the sun. The photochromic effect is clear, especially since the starting composition is not very colored and transparent. The

<Desc / Clms Page number 30>

 the speed of the effect on UV excitation and relaxation is remarkable.

EXAMPLE 6 A polar gloss for the lips comprising (% by weight) was prepared: - Reversacol Ruby 0.2% - octyl-2 dodecanol 10% - fumed silica 6% - castor oil qs 100% 8a of the oily phase> 7 (J / cm 3) A semi-thick gel of dark garnet initial color is obtained. The solvatochrome effect is very visible.

EXAMPLE 7 A lipstick comprising (% by weight) was prepared: Reversacol Ruby 0.2% Polyethylene wax 15% Hydrogenated polyisobutene (# a = 0) qs 100% A white initial color stick was obtained very slightly orange, which becomes very deep dark orange after exposure for a few seconds in the sun. The return to the initial color is also fast.

Example 8 A lipstick comprising (% by weight) was prepared: - Reversacol Ruby 0.05% - octyl-2 dodecanol 10% - fluid lanolin oil 10% - polyethylene wax 15% - castor oil qs 100 % A stick of light pink initial color is obtained which becomes deep dark orange after exposure a few seconds to the sun.

There is a very important photochromic effect with a high quality of return to the not excited state in terms of speed and recovery of the lack of color (the return is like the excitation in a few seconds).

Claims (25)

in which: R1 represents: - (i) a hydrogen atom; (ii) a hydrocarbon group having 1 to 30, preferably 1-18, and preferably 1 to 12, or even 1 to 6, branched or cyclic linear, saturated or unsaturated, carbon atoms optionally containing 1 to 5 heteroatoms chosen from N, O, S, Si and P, and / or optionally halogenated or perhalogenated, especially by FI, Br and / or Cl; (iii) a hydrocarbon ring formed with one of the bonds "f" or "gh" and the radical R7; or - (iv) a group chosen from -COOR4, -C (O) NR2R3, -NR2R3, -OR4 and SR4, in which: R2 and R3 represent, independently of one another, a hydrocarbon group having 1 to 20, preferably 1-12, and more preferably 1 to 6, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally having 1 to 5 heteroatoms selected from N, O, S, Si and P, taken together with the nitrogen atom to which they are attached form a saturated or unsaturated hydrocarbon heterocycle having 3-10, preferably 4-6, carbon atoms and optionally 1-5 other heteroatoms selected from N, O, S , Si and P, said ring being optionally substituted with at least one hydrocarbon radical having 1 to 20, preferably 1-15, and more preferably 1 to 6, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally containing 1 with 5 heteroatoms selected from N, O, S, Si and P; - R4 represents a hydrocarbon group having 1 to 20, preferably CLAIMS 1. Cosmetic composition comprising, in a cosmetically acceptable medium, at least one oily phase and at least one dye of formula (I) or (II): <Desc / Clms Page number 32>  1-15, and more preferably 1 to 6, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally halogenated or perhalogenated, especially by FI, Br and / or Cl, and / or optionally comprising 1 to 5 heteroatoms chosen from N, O, S, Si and P; R5 and R6 represent, independently of one another, a group chosen from: - (i) saturated cyclic aminoaryl groups of formula (IIa) or (IIb):

 wherein the ring having N and X is a saturated ring which comprises a total of 3 to 30 atoms, preferably 4-10 and most preferably 5, 6 or 7 atoms, including nitrogen, the balance being carbon atoms and or heteroatoms selected from O, S, Si, P and / or groups selected from -NH and -NR with R representing a hydrocarbon radical having 1 to 20, preferably 1-15, and more preferably 1 to 6, carbon atoms linear, branched or cyclic, saturated or unsaturated, optionally containing 1 to 5 heteroatoms selected from N, O, S, Si and P; - (ii) the indolinoaryl groups of formula (III): <Tb> <tb> (IIa) <SEP> (IIb) <tb> X <SEP> R9 <tb> # <SEP> # <tb> # <SEP> X <tb> R8 <SEP> # <tb> R8 <SEP> # <Tb> <Desc / Clms Page number 33>  wherein m and p are, independently of one another, integers ranging from 2 to 5; (iv) unsaturated cyclic aminoaryl groups of formulas (Va),

 in which R10 and R11 represent, independently of one another, a group chosen from (i) hydrocarbon groups having 1 to 30, preferably 1-18, and more preferably 1 to 12, or even 1-6, atoms of carbon, branched or cyclic linear, saturated or unsaturated, optionally containing 1 to 5 heteroatoms selected from N, O, S, Si and P, and / or optionally halogenated or perhalogenated, especially by FI, Br and / or CI; (ii) halogen atoms, and especially FI, Br and / or Cl; (iii) CN (nitrile), -COOH (carboxylate), -NO2 (nitro) groups; (iv) a hydrogen atom; a group selected from -C (O) NR 2 R 3, -NR 2 R 3, -OR 4 or -SR 4 with R 2, R 3 and R 4 having the meanings given above; (vi) the radicals R10 and R11 may together form a saturated or unsaturated hydrocarbon ring having a total of 5 to 8 atoms (including the atoms of the indoline ring), said atoms being chosen from C, O, S and / or NR with R representing H or a hydrocarbon radical having 1 to 20 carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally containing 1 to 5 heteroatoms chosen from N, O, S, Si and P; - (iii) groups of formula ( IV):

<Desc / Clms Page number 34>  in which R8 and R9 represent, independently of one another, a group chosen from (i) hydrocarbon groups having 1 to 30, preferably 1-18, and more preferably 1 to 12 or even 1-6, atoms saturated or unsaturated branched or cyclic linear carbon compounds, optionally containing 1 to 5 heteroatoms selected from N, O, S, Si and P, and / or optionally halogenated or perhalogenated, in particular by FI, Br and / or Cl; (ii) halogen atoms, and especially FI, Br and / or Cl; (iii) CN (nitrile), -COOH (carboxylate), -NO2 (nitro) groups; (iv) a hydrogen atom; (v) a group selected from -C (O) NR 2 R 3, -NR 2 R 3, OR 4 or -SR 4 with R 2, R 3 and R 4 having the meanings given above; (v) a hydrocarbon group having 1 to 30, preferably 2-18, and more preferably 3 to 12, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally containing 1 to 5 heteroatoms chosen from N, 0, S, Si and P; and in particular a group chosen from -C6H4-CONR2R3, -C6H4-NR2R3 and C6H4-OR4 with R2, R3 and R4 having the meanings given above; R7 represents a group chosen from: (i) hydrocarbon groups having 1 to 30, preferably 1-18, and more preferably 1 to 12, carbon atoms, branched or cyclic, saturated or unsaturated, optionally comprising 1 to 5 heteroatoms selected from N, O, S, Si and P,

 (Vb) or (Vc): <Desc / Clms Page number 35>  and / or optionally halogenated or perhalogenated, in particular by FI, Br and / or Cl; - (ii) the halogen atoms, and in particular FI, Br and / or CI; (iii) CN (nitrile), -COOH (carboxylate), -NO2 (nitro) groups; -N = N- (azo); = NH (imino); -CONH2 (amide); - (iv) a hydrogen atom; (v) a group chosen from -C (O) NR 2 R 3, -NR 2 R 3, -OR 4 or -SR 4 with R 2, R 3 and R 4 having the meanings given above; (vi) the radical R7 may additionally form, with one of the bonds "i", "j", "k", or "g, h" taken with the radical R1, or "f" taken with the radical R1, a saturated hydrocarbon ring having a total of 3 to 8, preferably 4 to 7, and more preferably 5 or 6, carbon atoms, optionally having 1 to 5 heteroatoms selected from N, O, S, Si and P; R'1 represents a group chosen from: - (i) a hydrogen atom; (ii) a hydrocarbon group having 1 to 30, preferably 1-18, and preferably 1 to 12, branched or cyclic linear, saturated or unsaturated carbon atoms, optionally containing 1 to 5 heteroatoms chosen from N, O, S; , Si and P, and / or optionally halogenated or perhalogenated, especially by FI, Br and / or CI; (iii) a group chosen from -C (O) NR 2 R 3, -NR 2 R 3, -OR 4 and -SR 4, with R 2, R 3 and R 4 having the meanings given above; R'2 represents a group chosen from: (i) hydrocarbon groups having 1 to 30, preferably 1-18, and more preferably 1 to 12, branched or cyclic linear, saturated or unsaturated carbon atoms, optionally containing 1 with 5 heteroatoms chosen from N, O, S, Si and P, and / or optionally halogenated or perhalogenated, in particular by FI, Br and / or Cl; - (ii) the halogen atoms, and in particular FI, Br and / or CI; (iii) CN (nitrile), -COOH (carboxylate), -NO2 (nitro) groups; -N = N- (azo); = NH (imino); -CONH2 (amide); - (iv) a hydrogen atom; (v) a group chosen from -C (O) NR 2 R 3, -NR 2 R 3, -OR 4 or -SR 4 with R 2, R 3 and R 4 having the meanings given above. 2. Composition according to claim 1 wherein the photochromic organic dye has one of the following formulas (Ia) and (IIa): <Desc / Clms Page number 36>  in which R1, R5, R6, R7, R'1 and R'2 are defined as in claim 1.

3. Composition according to one of the preceding claims, wherein R1 represents a hydrogen atom; a hydrocarbon ring with one of the "f" or "gh" bonds and the radical R7; or a group chosen from -COOR4, -NR2R3, OR4 and -SR4, in which: R2 and R3 represent, independently of one another, a hydrocarbon group having 1 to 20, preferably 1-15, and preferably 1 to 6 carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally having 1 to 5 heteroatoms selected from N, O, S, Si and P, taken together with the nitrogen atom to which they are connected, form a hydrocarbon heterocycle, saturated or unsaturated, comprising 3-10, preferably 4-6, carbon atoms and optionally 1-5 other heteroatoms selected from N, O, S, Si and P, said ring being optionally substituted by at least one hydrocarbon radical having 1 to 20, preferably 1 to 15, and more preferably 1 to 6, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally containing 1 to 5 heteroatoms chosen from N, O, S, Si and P; R 4 represents a hydrocarbon group having 1 to 20, preferably 1 to 15, and more preferably 1 to 6, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally halogenated or perhalogenated, in particular by FI, Br and / or CI, and / or optionally comprising 1 to 5 heteroatoms selected from N, O, S, Si and P. 4. Composition according to one of the preceding claims, wherein R5 and R6 represent, independently of one another, a group chosen from: - saturated cyclic aminoaryl groups of formula (Ila) or (Ilb): <Desc / Clms Page number 37>  in which the ring containing N and X is a saturated ring which comprises in total 3 to 30 atoms, preferably 4-10 and even more preferably 5 or 7 atoms, including nitrogen, the remainder being carbon atoms and or heteroatoms selected from O, S, Si, P and / or groups selected from -NH and -NR with R representing a hydrocarbon radical having 1 to 20, preferably 1-15, and more preferably 1 to 6, carbon atoms linear, branched or cyclic, saturated or unsaturated, optionally containing 1 to 5 heteroatoms selected from N, O, S, Si and P; a hydrocarbon group having 1 to 30, preferably 2-18, and more preferably 3 to 12, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally containing 1 to 5 heteroatoms chosen from N, O, S; , Si and P; in particular a group chosen from -C6H4-CONR2R3, -C6H4-NR2R3 and -C6H4-OR4 with R2, R3 and R4 having the meanings given in claim 1.

5. Composition according to one of the preceding claims, wherein R7 represents a group chosen from: - (i) hydrocarbon groups having 1 to 30, preferably 1-18, and more preferably 1 to 12, branched linear carbon atoms or cyclic, saturated or unsaturated, optionally comprising 1 to 5 heteroatoms selected from N, O, S, Si and P, and / or optionally halogenated or perhalogenated, especially by FI, Br and / or CI; - (ii) the halogen atoms, and in particular FI, Br and / or CI; (iii) CN (nitrile), -COOH (carboxylate), -NO2 (nitro) groups; -N = N- (azo); = NH (imino); -CONH2 (amide); - (iv) a hydrogen atom; (v) a group chosen from -NR 2 R 3, -OR 4 or -SR 4 with R 2, R 3 and R 4 having the meanings given in claim 1; (vi) the radical R7 may additionally form, with one of the bonds "i", "j", "k", or "g, h" taken with the radical R1, or "f" taken with the radical R1, a saturated hydrocarbon ring having in total 3 to 8, preferably 4 to 7, and more preferably 5 or 6, carbon atoms, optionally comprising 1 to 5 heteroatoms selected from N, O, S, <Desc / Clms Page number 38>  Si and P. 6. Composition according to one of the preceding claims, wherein R'1 represents hydrogen or a hydrocarbon group having 1 to 30, preferably 1-18, and preferably 1 to 12 carbon atoms, branched or cyclic linear, saturated or unsaturated, optionally containing 1 to 5 heteroatoms selected from N, O, S, Si and P, and / or optionally halogenated or perhalogenated, especially by FI, Br and / or CI. 7. Composition according to one of the preceding claims, in which R'2 represents hydrogen or a group chosen from -NO2, -NR2R3 and C (O) NR2R3, in which R2 and R3 represent independently one on the other, a hydrocarbon group having 1 to 20, preferably 1-12, and more preferably 1 to 6, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally having 1 to 5 heteroatoms selected from N , 0, S, Si and P; taken together with the nitrogen atom to which they are attached, form a saturated or unsaturated hydrocarbon heterocycle, having 3-10, preferably 4-6, carbon atoms and optionally 1-5 other heteroatoms selected from N, 0, S, Si and P, said ring being optionally substituted with at least one hydrocarbon radical having 1 to 20, preferably 1-15, and more preferably 1 to 6, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally containing 1 to 5 heteroatoms selected from N, O, S, Si and P.

 and / or R5 and R6 represent, independently of one another, either (i) a group of formula (IIa):

8. Composition according to one of the preceding claims, wherein the organic dye is of formula (I) or (la) for which: R1 represents hydrogen; or a COOR group with R being a saturated hydrocarbon radical having 1 to 12, preferably 1-6, carbon atoms, and especially a methyl or ethyl radical; or a group <Desc / Clms Page number 39>  in which R is a saturated hydrocarbon radical having 1 to 12, preferably 1-6, carbon atoms, and especially a methyl or ethyl radical; and R2 and R3 are, independently of one another, a hydrocarbon group having 1 to 20, preferably 1-15, and more preferably 1 to 6, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally having 1 to 5 heteroatoms selected from N, O, S, Si and P; and / or R7 represents a hydrogen atom or a group -NR2R3, with R2 and R3 representing, independently of one another, a linear or branched, saturated hydrocarbon group having 1 to 12, preferably 1- 6, carbon atoms, and in particular a methyl and / or ethyl group.

 or (ii) a hydrocarbon group having 5 to 14, preferably 6 to 10 carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally comprising 1 to 2 heteroatoms chosen from N, O or S; especially a group

 wherein the ring having N and X is a saturated ring which comprises in total 4 to 7 atoms, especially 5 or 6 atoms, including nitrogen, and especially 3-5 carbon atoms and 0-1 oxygen atom ; in particular a group of formula: 9. Composition according to one of claims 1 to 7, wherein the organic dye is of formula (II) or (IIa) for which: R'1 represents hydrogen or a group-COOR with R being a hydrocarbon radical saturated having 1 to 12, preferably 1-6, carbon atoms, and especially a methyl or ethyl radical; and / or R5 and R6 represent, independently of one another, either (i) a group of formula (IIa): <Desc / Clms Page number 40>  in which R is a saturated hydrocarbon radical having 1 to 12, preferably 1-6, carbon atoms, and especially a methyl or ethyl radical; and R2 and R3 are, independently of one another, a hydrocarbon group having 1 to 20, preferably 1-15, and more preferably 1 to 6, carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally having 1 to 5 heteroatoms selected from N, O, S, Si and P; and / or R'2 represents hydrogen, or a group-NR'R "with R 'and R", identical or different, representing a linear or branched, saturated hydrocarbon group having 1 to 12, preferably 1- 6, carbon atoms, and especially a methyl and / or ethyl group; or a group

 or (ii) a hydrocarbon group having 5 to 14, preferably 6 to 10 carbon atoms, linear, branched or cyclic, saturated or unsaturated, optionally comprising 1 to 2 heteroatoms chosen from N, O or S; in particular a grouping:

 wherein the ring having N and X is a saturated ring which comprises in total 4 to 7 atoms, especially 5 to 6 atoms, including nitrogen, and especially 4-5 carbon atoms and 0-1 oxygen atom ; in particular a group of formula:

<Desc / Clms Page number 41>  3-phenyl-3- (4-piperidinophenyl) -6-morpholino-3H-naphtho [2,1-b] pyran of formula:

 3-phenyl-3- (4-morpholinophenyl) -6-morpholino-3H-naphtho [2,1-b] pyran of formula:

 10. Composition according to one of the preceding claims, wherein the organic dye is chosen from: - 3,3-di (4-methoxyphenyl) -6-morpholino-3H-naphtho [2,1-b] pyran of formula :

<Desc / Clms Page number 42>  - their mixtures.

 2-phenyl-2- (4-piperidinophenyl) -5-carboxymethyl-9-N-dimethyl-2H-naphtho [1,2-b] pyran of formula:

 3-phenyl-3- (4-piperidinophenyl) -6-carboxymethyl-9-N-dimethyl-3H-naphtho [2,1-b] pyran of formula:

11. Composition according to one of the preceding claims, wherein the organic dye according to the invention is included, alone or as a mixture, in an amount of 0.001 to 20% by weight, in particular from 0.005 to 10% by weight, preferably 0.01 to 5% by weight, and more preferably 0.05 to 2% by weight, preferably 0.1 to 1% by weight, based on the total weight of the cosmetic composition. <Desc / Clms Page number 43>  tick. 12. Composition according to one of the preceding claims, wherein the oily phase is polar and has an average solubility parameter #a according Hansen solubility space at 25 C, greater than or equal to 5.0 (J / cm3), in particular greater than or equal to 5.3, even greater than or equal to 5.5 and even better than or equal to 6.0 (J / cm3), or even greater than or equal to 7.0 (J / cm3). 13. Composition according to one of the preceding claims wherein the oily phase comprises 5 to 100% by weight, especially 10-90%, or even 15-60% and more preferably 20-50% by weight of the total weight of said oily phase of one or more polar oils having an average solubility parameter 8a according to the Hansen solubility space, at 25 ° C., greater than or equal to 5.0 (J / cm 3). 14. Composition according to one of claims 1 to 11, wherein the oily phase is apolar and has a mean solubility parameter #a according Hansen solubility space at 25 C, less than 5.0, especially lower or 4.9, more preferably 4.5 or less, and still more preferably 4.0 or less (J / cm3). 15. Composition according to one of claims 1-11 and 14, wherein the oily phase comprises 5 to 100% by weight, in particular 10-90%, or even 15-60% and even more preferably 20-50% by weight of the weight. total of said oil phase, one or more apolar oils having a mean solubility parameter #a according Hansen solubility space, at 25 C, less than 5.0 (J / cm3). 16. Composition according to one of the preceding claims, wherein the oily phase comprises at least one oil chosen from: - animal or vegetable oils formed by fatty acid esters and polyols, in particular liquid triglycerides, for example sunflower, corn, soy, squash, grape seed, sesame, hazelnut, apricot, almond or avocado oils; fish oils, tricaprocaprylate glycerol, or vegetable or animal oils of formula R1COOR2 wherein R1 represents the residue of a higher fatty acid having 7 to 19 carbon atoms and R2 represents a branched hydrocarbon chain containing from 3 to 20 carbon atoms, for example, Purcellin oil; paraffin oil, petrolatum, calophyllum, macadamia, rapeseed, copra, peanut, palm, castor oil, jojoba, olive or cereal sprouts; shea butter oil ; perhydrosqualene; esters and synthetic ethers, in particular of fatty acids, such as the oils of formula R 1 COOR 2 in which R 1 represents the residue of a higher fatty acid having from 7 to 29 carbon atoms and R 2 represents a hydrocarbon-based chain containing from 3 to 30 carbon atoms; carbon atoms like for example the my- <Desc / Clms Page number 44>  isopropyl ristate, 2-ethylhexyl palmitate, octyl-2-dodecyl stearate, octyl-2-dodecyl erucate, isononyl isononanoate, isostearyl isostearate; hydroxylated esters such as isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, triisocetyl citrate, heptanoates, octanoates and decanoates of fatty alcohols; polyol esters such as propylene glycol dioctanoate, neopentyl glycol diheptanoate, diethylene glycol diisononanoate; pentaerythritol esters such as pentaerythritol tetraisostearate; esters of the tridecyl trimellitate type; fatty alcohols having from 12 to 26 carbon atoms, such as octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol and oleyl alcohol. linear or branched hydrocarbons of mineral or synthetic origin, such as liquid paraffins and their derivatives, petroleum jelly, polydecenes, and hydrogenated polyisobutene such as parleam; isoparaffins such as isohexadecane and isodecane; glycerides and in particular acetylglycerides or triglycerides of fatty acids having 4 to 10 carbon atoms, such as triglycerides of heptanoic, octanoic and capric / caprylic acids. 17. Composition according to one of the preceding claims, wherein the oily phase comprises at least one oil selected from octyldodecanol, hexyldecanol, octyldecanol, oleic alcohol, castor oil, diisostearyl malate. , glyceryl triheptanoate, glyceryl trioctanoate, capric / caprylic acid triglyceride, triisononanoïn, tridecyl trimellitate, aliphatic hydrocarbons, especially C 6 -C 40 hydrocarbons, such as paraffin oils, volatile oils, such as isohexadecane or isododecane, or non-volatile, and their derivatives; petroleum jelly, hydrogenated or non-hydrogenated polydecenes, hydrogenated polyisobutene such as Parleam oil, squalane, polybutylenes, isononyl isononanoate; fluorinated oils, especially perfluorinated oils, and mixtures thereof. 18. Composition according to one of the preceding claims, wherein the oily phase is in an amount of 1 to 99% by weight, especially 10 to 90% by weight, preferably 15 to 80% by weight, relative to the weight. total of the cosmetic composition. 19. Composition according to one of the preceding claims, further comprising other fatty substances chosen from waxes, gums and / or pasty fatty substances of animal, vegetable, mineral or synthetic origin, and mixtures thereof. 20. Composition according to one of the preceding claims, further comprising a particulate phase, which may comprise pigments and / or nacres and / or fillers; and / or dyes; and / or photochromic compounds other <Desc / Clms Page number 45>  photochromic organic dyes of formula (I) or (II); and / or UV filters. 21. Composition according to one of the preceding claims, having an AE greater than or equal to 5, preferably greater than or equal to 10, better than or equal to 25, more preferably greater than or equal to 35, or even greater than or equal to 45. 22. Composition according to one of the preceding claims, being in the form of a care product and / or make-up of the skin of the body or face, lips and hair, a sun product or self-tanning, even a hair product. 23. Composition according to one of the preceding claims, in the form of a lipstick, a foundation, a blush or eyeshadow, a loose powder or compact, of a tinted cream, a body make-up product, a skin coloring product, an eyeliner or a mascara. 24. Process for the cosmetic treatment of a support chosen from the mucous membranes, the semi-mucous membranes, the skin and / or the integuments, in which a cosmetic composition as defined in one of Claims 1 to 23 is applied to said support. . 25. A process for temporary makeup and / or coloring of a support chosen from the mucous membranes, the semi-mucous membranes, the skin and / or the integuments, in which a cosmetic composition as defined in one of the compositions is applied to said support. Claims 1 to 23.