FR2818143A1 - Photoprotective cosmetic or dermatological composition useful for e.g. a sunscreen, comprises a benzotriazole-functional silicon-containing filter and a 4,4-diarylbutadiene filter - Google Patents

Abstract

Cosmetic or dermatological composition for topical use comprises: (1) 0.5-15 wt.% of a benzotriazole-functional silicon-containing filter; and (2) 0.5-15 wt.% of a 4,4-diarylbutadiene filter.

Description

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The invention relates to novel cosmetic or dermatological compositions for topical use, in particular for the photoprotection of the skin and / or the hair, characterized in that they comprise at least one embodiment of the present invention. in a cosmetically acceptable carrier, at least: (i) from 0.5 to 15% by weight of a benzotriazol-functional silicon derivative as the first filter; (ii) from 0.5 to 15% by weight of a 4,4-diarylbutadiene compound as a second filter; said first and second filters being present in said compositions in a proportion producing a synergistic activity at the conferred sun protection levels.

The invention also relates to their applications for the protection of the skin and hair against the effects of ultraviolet radiation.

It is known that light radiation with wavelengths between 280 nm and 400 nm enables the browning of the human epidermis and that wavelength rays between 280 and 320 nm, known under the name UV- B, cause erythema and skin burns that can hinder the development of natural tanning; this UV-B radiation must therefore be filtered.

It is also known that UV-A rays of wavelengths between 320 and 400 nm, which cause browning of the skin, are capable of inducing an alteration thereof, especially in the case of a skin sensitive or skin continuously exposed to solar radiation. UV-A rays cause in particular a loss of elasticity of the skin and the appearance of wrinkles leading to premature aging. They promote the triggering of the erythematous reaction or amplify this reaction in some subjects and may even be the cause of phototoxic or allergic photo reactions. It is therefore desirable to also filter the UV-A radiation.

Numerous cosmetic compositions intended for the photoprotection (UV-A and / or UV-B) of the skin have been proposed to date.

These antisolar compositions are quite often in the form of an oil-in-water emulsion (that is to say a cosmetically acceptable support consisting of an aqueous dispersant continuous phase and an oily disperse discontinuous phase) which contains at various concentrations, one or more conventional organic filters, lipophilic and / or hydrophilic, capable of selectively absorbing harmful UV radiation, these filters (and their amounts) being selected according to the desired sun protection factor, the sunscreen (SPF) expressed mathematically by the ratio of the UV radiation dose necessary to reach the erythematogenic threshold with the UV filter with the dose of UV radiation necessary to reach the erythematogenic threshold without UV filter.

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 Cosmetic UV filters are known from lipophilic benzotriazol-functional silicone derivatives having good filtering properties both in the field of UV-A radiation and in the field of UV-B radiation. They are described in applications EP-A-0392883; EP-A-0660701; EP-A-0708108; EP-A-0711778; In applications EP-A-0742003 and EP-A-0860165, it has already been proposed to associate with these benzotriazol-functional silicone filters water-soluble filters with a particular sulphonic function, namely benzene acid 1,4. -di (3-methylidene-10-camphosulphonic acid) or 2-phenyl benzimidazol-5-sulfonic acid and its salts, in order to produce a synergistic activity at sun protection levels. These synergetic filter systems require the use of at least one aqueous phase solubilizing the water-soluble filter and a fatty phase to solubilize the silicone filter; which significantly reduces the possibilities of formulation.

Following extensive research in the field of photoprotection mentioned above, the Applicant has discovered, unexpectedly and surprisingly, a combination of three families of particular filter compounds and already known per se in the state Of the art (1) a silicon derivative of benzotriazol and (2) a 4,4-diarylbutadiene afforded, because of a synergistic effect, to obtain antisolar compositions with significantly improved sun protection factors. Such an association made it possible to obtain solar compositions whose sun protection indices are markedly improved, and in any case much greater than those which can be obtained either with one or the other of the filters used alone.

In addition, the particular combination of filters according to the invention can be easily incorporated into a very wide range of cosmetic media.

This discovery is the basis of the present invention.

Thus, according to one of the objects of the present invention, it is now proposed new cosmetic compositions, in particular antisolar, which are characterized in that they comprise, in a cosmetically acceptable carrier, at least: (i) from 0.5 to 15% by weight of at least one benzotriazol-functional silicon derivative as a first filter; (ii) from 0.5 to 15% by weight of at least one 4,4-diarylbutadiene compound as a second filter; said first and second filters being present in said compositions in a proportion producing a synergistic activity at the conferred sun protection levels.

The present invention also relates to the use of the above compositions for the manufacture of cosmetic compositions for the protection of the skin and / or the hair against ultraviolet radiation, in particular solar radiation.

Other features, aspects and advantages of the present invention will appear on reading the detailed description which follows.

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 By 4, 4-diarylbutadiene compound according to the invention is meant any molecule comprising at least one chromophore group 4, 4-diarylbutadiene.

This may be in the form of a simple compound, an oligomer or a polymer having on the chain grafts containing the chromophore group.

dans laquelle :

- Y, identiques ou différents, sont choisis parmi les radicaux alkyles en Cl-C8, les halogènes et les radicaux alkoxy en Cl-C4 étant entendu que, dans ce dernier cas, deux Y adjacents d'un même noyau aromatique peuvent former ensemble un groupement alkylidène dioxy dans lequel le groupe alkylidène contient de 1 à 2 atomes de carbone, - X représente 0 ou NH, - Z représente l'hydrogène ou un radical alkyle en Ci-C4, - n est un nombre entier compris entre 0 et 3 inclusivement, - m est 0 ou 1, - p représente un nombre entier compris entre 1 et 10, inclusivement. The benzotriazol-functional silicic derivatives used in the present invention are preferably silanes or benzotriazol-functional siloxanes comprising at least one unit of the following formula (1):
0 (3-a) / 2 Si (R7) -G (1) wherein - R7 represents an optionally halogenated C1-C10 alkyl radical or a phenyl radical or a trimethylsilyloxy radical, - a is an integer selected from 0 and 3 inclusive, and the symbol G denotes a monovalent radical directly attached to a silicon atom, and which corresponds to the following formula (2):

in which :

Y, which are identical or different, are chosen from C1-C8 alkyl radicals, halogens and C1-C4 alkoxy radicals, it being understood that, in the latter case, two adjacent Y's of one and the same aromatic nucleus may together form a alkylidene dioxy group in which the alkylidene group contains from 1 to 2 carbon atoms, - X represents 0 or NH, - Z represents hydrogen or a C1-C4 alkyl radical, - n is an integer between 0 and 3 inclusive, - m is 0 or 1, - p is an integer from 1 to 10, inclusive.

These compounds are in particular described in patent applications EP-A-0392883; EP-A-0660701; EP-A-0708108; EP-A-0711778; EP-A-711779.

Preferably, the silicon derivatives used in the context of the present invention belong to the general family of benzotriazole silicones which is described in particular in EP-A-0660701.

A family of benzotriazole silicones that are particularly suitable for carrying out the present invention is that comprising the compounds corresponding to the following formulas (5) or (6):

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dans lesquelles : - R7, identiques ou différents, sont choisis parmi les radicaux alkyles en C1-C10, phényle, trifluoro-3, 3,3 propyle et triméthylsilyloxy, au moins 80% en nombre des radicaux R7 étant méthyle, - D, identiques ou différents sont choisis parmi les radicaux R7 et le radical G, - r est un nombre entier compris entre 0 et 50 inclusivement, et s est un nombre entier compris entre 0 et 20 inclusivement, et si s = 0, au moins l'un des deux symboles D désigne G, - u est un nombre entier compris entre 1 et 6 inclusivement, et t est un nombre entier compris entre 0 et 10 inclusivement, étant entendu que t + u est égal ou supérieur à 3, - et le symbole G répond à la formule (2) ci-dessus.

in which: R7, which are identical or different, are chosen from C1-C10 alkyl, phenyl, 3,3,3-trifluoro-propyl and trimethylsilyloxy radicals, at least 80% by number of the R7 radicals being methyl, -D, identical; or different are selected from radicals R7 and radical G, - r is an integer from 0 to 50 inclusive, and s is an integer from 0 to 20 inclusive, and if s = 0, at least one of the two symbols D denotes G, - u is an integer between 1 and 6 inclusive, and t is an integer between 0 and 10 inclusive, provided that t + u is equal to or greater than 3, - and the symbol G meets the formula (2) above.

De préférence, cet accrochage se fait en position 3,4, 5 (noyau aromatique portant la fonction hydroxy) ou 4' (noyau benzénique adjacent le cycle triazolé), et As can be seen from the formula (2) given above, the attachment of the - (X) - (CH 2) p -CH (Z) -CH 2 - linkage to the benzotriazol unit, which thus ensures the connection of said benzotriazol unit to the silicon atom of the silicone chain may, according to the present invention, be used in all the available positions offered by the two aromatic rings of benzotriazol:

Preferably, this attachment is at position 3,4, 5 (aromatic ring bearing the hydroxy function) or 4 '(benzene ring adjacent the triazole ring), and

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 even more preferably in position 3, 4 or 5. In a preferred embodiment of the invention, the attachment is in position 3.

Likewise, the attachment of the substituent unit (s) Y can take place in all the other positions available within benzotriazol. However, preferably, this attachment is in the position 3,4, 4 ', 5 and / or 6. In a preferred embodiment of the invention, the attachment of the Y pattern is in position 5.

In the formulas (5) and (6) above, the alkyl radicals may be linear or branched and chosen in particular from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl radicals. n-amyl, isoamyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl and ter-octyl. The preferred R7 alkyl radicals according to the invention are the methyl, ethyl, propyl, n-butyl, noctyle and 2-ethylhexyl radicals. Even more preferably, the radicals R7 are all methyl radicals.

Among the compounds of formulas (5) or (6) above, it is preferred to use those corresponding to formula (5), that is to say short-chain linear diorganosiloxanes.

- m=O, ou [m=1 et X=O] - p est égat à 1. Among the compounds of formulas (5) above, it is preferred to use those for which the radicals D are both radicals R7. Among the linear diorganosiloxanes falling within the scope of the present invention, statistical derivatives are more particularly preferred. or else defined in blocks having at least one, and even more preferably all, of the following characteristics: - D is a radical R7 - R7 is alkyl and even more preferably is methyl, - r is between 0 and 15 inclusive ; s is between 1 and 10 inclusive, - n is non-zero, and preferably 1, and Y is then selected from methyl, tert-butyl or C 1 -C 4 alkoxy; Z is hydrogen or methyl,

- m = 0, where [m = 1 and X = O] - p is equal to 1.

A family of benzotriazole silicones that are particularly suitable for the invention is that defined by the following general formula (7):

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avec 0 < r < 10, 1 < s < 10, et où E représente le radical divalent

Dans une forme particulièrement préférée de réalisation de l'invention, la silicone benzotriazol est le composé Drométrizole Trisiloxane (nom CTFA) répondant à la formule suivante :

Des procédés convenant à la préparation des produits de formule (1), (5), (6) et (7) ci-dessus sont notamment décrits dans les brevets américains US3, 220, 972,

US3, 697, 473, US4, 340, 709, US4, 316, 033, US4, 328, 346 et dans les demandes de brevet EP-A-0392883 et EP-A-0742 003.

with 0 <r <10, 1 <s <10, and where E represents the divalent radical

In a particularly preferred embodiment of the invention, the benzotriazol silicone is the compound Drométrizole Trisiloxane (CTFA name) corresponding to the following formula:

Processes suitable for the preparation of the products of formulas (1), (5), (6) and (7) above are described in particular in US Pat.

US 3, 697, 473, US 4, 340, 709, US 4, 316, 033, US 4, 328, 346 and in EP-A-0392883 and EP-A-0742 003.

The silicone derivative with benzotriazol function is present in the compositions according to the invention at contents ranging preferably from 1 to 10%, by weight, always relative to the total weight of the composition.

Among the preferred compounds 4, 4-diarylbutadienes according to the invention, it is possible to choose the compounds corresponding to the following formula (tut):

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dans laquelle le système diène est de configuration Z, Z ; Z, E ; E, Z ou E, E ou des mélanges desdites configurations et où : 2 - R et R, identiques ou différents, désignent hydrogène, un radical alkyle en C1-C20, linéaire ou ramifié ; un radical alcényle en Cz-Cio ; un radical alcoxy en C1-C12 ; un radical cycloalkyle en C3-C10 ; un radical cycloalcényle en Cs-Cio ; un radical alcoxycarbonyle en C1-C20 linéaire ou ramifié ; un radical monoalkylamino en Ci-Ci2, linéaire ou ramifié ; un radical dialkylamino en Cl-Cl2, linéaire ou ramifié ; un aryle ; un hétéroaryle ou un substituant hydrosolubilisant choisi parmi un groupe carboxylate, un groupe sulfonate ou un reste ammonium ; - R désigne un groupe COOR ; COR5 ; CONR5R6 ; CN ; un radical alkyle en Ci- C20, linéaire ou ramifié ; un radical alcényle en C2-C1o ; un radical cycloalkyle en Cs-Cio ; un radical bicycloalkyle en C7-C10 ; un radical cycloalcényle en Cs-Cio ; un radical bicycloalcényle en Cp-Cio ; un aryle en Ce-Cia ; un hétéroaryle en C3-C7 ; - R4 désigne un groupe COOR6 ; COR6 ; CONRsR6 ; CN ; un radical alkyle en Ci- C20, linéaire ou ramifié ; un radical alcényle en C2-C1o ; un radical cycloalkyle en C3-C10 ; un radical bicycloalkyle en C7-C10 ; un radical cycloalcényle en C3-C10; ;

un radical bicyc) oa) cény) e en Cy-Cio ; un aryle ; un hétéroaryle ; - R5 et R'identiques ou différents, désignent hydrogène ; [V) o-R, C1-C6-alkylène-SO3U ; Ci-C6-alkylène-PO3U ; C1-C6-alkylène-N (R AA ; un radical alkyle en Ci-Czo. linéaire ou ramifié ; un radical alcényle en C2-C10 ; un radical cycloalkyle en C3-C10; un radical bicycloalkyle en Cy-Cio ; un radical cycloalcényle en Cg-Cio ; un radical cycloalcényle en C7-C10 ; un aryle ; un hétéroaryle ; - V désigne un groupe-CH2-CH2-W-,-CH2CH2CH2W-,-CH (CH3)-CH2-W-, -CH2-CH2-CH2-CH2-W-, -CH2-CH(CH2CH3)-W-;

- A désigne CI, Br, l, S04R9 ; - U désigne hydrogène, Na+, K, Mg2+, Ca, U". At+,-N (R - W désigne 0 ou NH ; 51 - et ru identiques ou différents, désignent hydrogène, un radical alkyle en C1-C6. linéaire ou ramifié ; un radical alcényle en 2-Ce. linéaire ou ramifié ; un radical acyle en C1-C6 linéaire ou ramifié ; - R9 désigne hydrogène, un radical alkyle en Ci-Ce, linéaire ou ramifié ; un radical alcényle en C2-C6 ; - 1 varie de 1 à 3 ; - o varie de 0 à 150.

wherein the diene system is of Z, Z configuration; Z, E; E, Z or E, E or mixtures of said configurations and wherein: R 2 and R 2, which may be identical or different, denote hydrogen, a linear or branched C 1 -C 20 alkyl radical; a C 1 -C 10 alkenyl radical; a C1-C12 alkoxy radical; a C3-C10 cycloalkyl radical; a C 5 -C 10 cycloalkenyl radical; a linear or branched C1-C20 alkoxycarbonyl radical; a linear or branched C 1 -C 12 monoalkylamino radical; a linear or branched C 1 -C 12 dialkylamino radical; aryl; a heteroaryl or a water-solubilising substituent selected from a carboxylate group, a sulfonate group or an ammonium residue; - R denotes a group COOR; COR5; CONR5R6; CN; a linear or branched C 1 -C 20 alkyl radical; a C2-C10 alkenyl radical; a C 5 -C 10 cycloalkyl radical; a C7-C10 bicycloalkyl radical; a C 5 -C 10 cycloalkenyl radical; a C 1 -C 10 bicycloalkenyl radical; an aryl in Ce-Cia; a C3-C7 heteroaryl; - R4 denotes a COOR6 group; COR6; CONRsR6; CN; a linear or branched C 1 -C 20 alkyl radical; a C2-C10 alkenyl radical; a C3-C10 cycloalkyl radical; a C7-C10 bicycloalkyl radical; a C 3 -C 10 cycloalkenyl radical; ;

a bicyclo (o) alkoxy radical of C 1 -C 10; aryl; a heteroaryl; - R5 and R 'identical or different, denote hydrogen; [V) oR, C1-C6-alkylene-SO3U; C1-C6-alkylene-PO3U; C1-C6-alkylene-N (R AA), a linear or branched C1-C20 alkyl radical, a C2-C10 alkenyl radical, a C3-C10 cycloalkyl radical, a bicycloalkyl radical at a C5-C10 radical or a cycloalkenyl radical; C 7 -C 10 C 7 -C 10 cycloalkenyl, aryl, heteroaryl, - V denotes a group -CH 2 -CH 2 -W -, - CH 2 CH 2 CH 2 W -, - CH (CH 3) -CH 2 -W-, -CH 2 CH 2 -CH 2 -CH 2 -W-, -CH 2 -CH (CH 2 CH 3) -W-;

A is CI, Br, 1, SO4R9; U denotes hydrogen, Na +, K, Mg 2+, Ca, U ", At +, - N (R - W denotes 0 or NH; 51 - and r 1, which may be identical or different, denote hydrogen, a linear C 1 -C 6 alkyl radical; branched; a linear or branched 2-C 6 alkenyl radical; a linear or branched C 1 -C 6 acyl radical; R 9 denotes hydrogen, a linear or branched C 1 -C 6 alkyl radical; a C 2 -C 6 alkenyl radical; - 1 varies from 1 to 3, - o varies from 0 to 150.

Examples of alkyl radicals that may be mentioned include: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-propyl,

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pentyl, 1-méthylbutyle, 2-méthylbutyle, 3-méthylbutyle, 2, 2-diméthylpropyle, 1- éthylpropyle, n-hexyle, 1, 1-diméthylpropyle, 1, 2-diméthylpropyle, 1-méthylpentyle, 2-méthylpentyle, 3-méthylpentyle, 4-méthylpentyle, 1, 1-diméthylbutyle, 1, 2diméthylbutyle, 1, 3-diméthylbutyle, 2, 2-diméthylbutyle, 2, 3-diméthylbutyle, 3, 3diméthylbutyle, 1-éthylbutyle, 2-éthylbutyle, 1, 2, 2-triméthylpropyle, 1-éthyl-1méthylpropyle, 1-éthyl-2-méthylpropyle, n-heptyle, n-octyle, n-nonyle, n-décyle, nundécyle, n-dodécyle, n-tridécyle, n-tétradécyle, n-pentadécyle, n-hexadécyle, nheptadécyle, n-octadécyle, n-nonadécyle ou n-eicosyle.

pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3- methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 2, 2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, n-heptyl, n-octyl, n-nonyl, n-decyl, nundecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n- pentadecyl, n-hexadecyl, nheptadecyl, n-octadecyl, n-nonadecyl or n-eicosyl.

Examples of C 2 -C 10 alkenyl groups which may be mentioned include: ethenyl, n-propenyl, 1-methylethenyl, n-butenyl, 1-methylpropenyl, 2-methylpropenyl, 1,1-dimethylethenyl, n-pentenyl, 1-methylbutenyl, 2-methylbutenyl, 3-methylbutenyl, 2,2-dimethylpropenyl, 1-ethylpropenyl, n-hexenyl, 1,1-dimethylpropenyl, 1,2-dimethylpropenyl, 1-methylpentenyl, 2-methylpentenyl, 3-methylpentenyl, 4-methylpentenyl, 1,1-dimethylbutenyl, 1,2-dimethylbutenyl, 1,3-dimethylbutenyl, 2,2-dimethylbutenyl, 2,3-dimethylbutenyl, 3,3-dimethylbutenyl, 1-ethylbutenyl, 2-ethylbutenyl, 1, 1, 2 trimethylpropyl, 1, 2, 2-trimethylpropenyl, 1-ethyl-1-methylpropenyl, 1-ethyl-2-methylpropenyl, n-heptenyl, n-octenyl, n-nonenyl, n-decenyl.

As C1-C12 alkoxy radicals for R and R2 radicals, mention may be made of: methoxy, n-propoxy, 1-methylethoxy, 1-methylpropoxy, n-pentoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-methyl 1-ethylpropoxy, octoxy, ethoxy, n-propoxy, n-butoxy, 2-methylpropoxy, 1,1-dimethylpropoxy, hexoxy, heptoxy, 2-ethylhexoxy.

C 3 -C 10 cycloalkyl radicals for R 6 and R 7 include, for example: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclopropyl, 1-ethylcyclopropyl, 1-propylcyclopropyl, 1-butylcyclopropyl, 1- pentylcyclopropyl, 1-methyl-1-butylcyclopropyl, 1, 2-dimethylcyclypropyl, 1-methyl-2-ethylcyclopropyl, cyclooctyl, cyclononyl or cyclodecyl.

As C 5 -C 10 cycloalkylene radicals having one or more double bonds, for the R 6 and R 7 radicals, mention may be made of: cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, 1,3-cyclohexadienyl, 1,4-cyclohexadienyl, cycloheptenyl, cycloheptameryl cyclooctenyl, 1,5-cyclooctadienyl, cyclooctterenyl, cyclononenyl or cyclodecenyl.

The cycloalkyl or cycloalkenyl radicals may comprise one or more substituents (preferably from 1 to 3) chosen, for example, from halogen such as chlorine, fluorine or bromine; cyano; nitro; amino; C1-C4-alkylamino; C1-C4 dialkylamino; C1-C4alkyl; C1-C4-alkoxy; hydroxy; they may also contain from 1 to 3 heteroatoms such as sulfur, oxygen or nitrogen, the free valencies of which may be saturated with a hydrogen or a C 1 -C 4 alkyl radical.

As acyl radicals, for example, formyl, acetyl, propionyl or n-butyryl may be mentioned.

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 The bicycloalkyl or bicycloalkyl groups are chosen, for example, from bicyclic terpenes such as the derivatives of pinane, bornane, pinene or camphor or adamantane.

The aryl groups are preferably chosen from phenyl or naphthyl rings, which may comprise one or more substituents (preferably from 1 to 3) chosen for example from halogen such as chlorine, fluorine or bromine; cyano; nitro; amino; C1-C4-alkylamino; C1-C4 dialkylamino; C1-4alkyl; C1-C4alkoxy, hydroxy. Particularly preferred are phenyl, methoxyphenyl and naphthyl.

The heteroaryl groups generally comprise one or more heteroatoms chosen from sulfur, oxygen or nitrogen.

The water-solubilising groups are for example carboxylate groups, sulphonates and more particularly their salts with physiologically acceptable cations such as alkali metal salts or trialkylammonium salts such as tri (hydroxyalkyl) ammonium or 2-methylpropan-1-ol salts. -2- ammonium. Mention may also be made of ammonium groups such as alkylammoniums and their salified forms with physiologically acceptable anions.

dans laquelle le système diène est de configuration Z, Z ; Z, E ; E, Z ou E, E ou des mélanges desdites configurations et où : - R1 et R2, identiques ou différents, désignent hydrogène, un radical alkyle en Ci-Ce ; un radical alcoxy en Ci-Cg ; un substituant hydrosolubilisant choisi parmi un groupe carboxylate, un groupe sulfonate ou un reste ammonium ; - R désigne un groupe COOR5 ; CONR5R6 ; CN ; - R4 désigne un groupe COOR6 ; CONR 5R 6 ; - R5 désigne hydrogène ; [V]o-R7 ; C1-C6-alkylène-SO3U ; C1-C6-alkylène-R(R8)3+ A- ; - R6 désigne Mo-R7 ; C1-C6-alkylène-SO3U ; Ci-C6-alkylène-N (R3+ A' ; - V désigne un groupe -CH2-CH2-O-, -CH2CH2CH2O-, -CH(CH3)-CH2-O-,

- A désigne CI, Br, l, S04R9 ; - U désigne hydrogène, Na+, K+, Mg,Ca2+,Li+, A)-N (R8) 4+ - R7, R et R9 identiques ou différents, désignent hydrogène, un radical alkyle en Cl-C3, linéaire ou ramifié ; The preferred compounds of formula (II) are chosen from those of formula (IIa) below:

wherein the diene system is of Z, Z configuration; Z, E; E, Z or E, E or mixtures of said configurations and wherein: - R1 and R2, identical or different, denote hydrogen, a C1-C6 alkyl radical; a C1-C8 alkoxy radical; a water-solubilising substituent selected from a carboxylate group, a sulfonate group or an ammonium residue; - R denotes a COOR5 group; CONR5R6; CN; - R4 denotes a COOR6 group; CONR 5R 6; - R5 is hydrogen; [V] o-R7; C1-C6-alkylene-SO3U; C1-C6-alkylene-R (R8) 3+ A-; - R6 denotes Mo-R7; C1-C6-alkylene-SO3U; C1-C6-alkylene-N (R3 + A ') - V is -CH2-CH2-O-, -CH2CH2CH2O-, -CH (CH3) -CH2-O-,

A is CI, Br, 1, SO4R9; - U denotes hydrogen, Na +, K +, Mg, Ca2 +, Li +, A) -N (R8) 4+ - R7, R and R9 identical or different, denote hydrogen, a linear or branched C1-C3 alkyl radical;

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- 1 varie de 1 à 3 - o varie de 0 à 50 ; Les composés de formule (II) encore plus préférentiels sont choisis parmi ceux répondant à la formule (lib) suivante :

- 1 varies from 1 to 3 - o varies from 0 to 50; The compounds of formula (II) that are even more preferred are chosen from those corresponding to the following formula (lib):

dans laquelle le système diène est de configuration Z, Z ; Z, E ; E, Z ou E, E ou des mélanges desdites configurations et où : 2 - R'et R2, identiques ou différents, désignent hydrogène, un radical alkyle en Cl-C8 ; un radical alcoxy en C1-C8 ; - R3 désigne un groupe COOR5 ; CONR5R6 ; CN ; - R4 désigne un groupe COOR ; CONR5R6 ; - R5 désigne hydrogène ; [V] o-R ; Ci-C6-alkylène-S03Y ; Ci-C6-alkylène-N (R8) 3+ A- ; - R6 désigne [V] o-R7 ; Ci-C6-alkylène-SO3U ; Ci-C6-alkylène-N (R A- ; - V désigne un groupe-CH2-CH2-0-,-CH2CH2CH2O-,-CH (CH3)-CH2-0-, - A désigne CI, Br, l, SO4R9 ; - U désigne hydrogène, Na+, K+, Mg2+, Ca2+, Li+, At,-N (R - R, R et R identiques ou différents, désignent hydrogène, un radical alkyle en Ci-Cg linéaire ou ramifié ; - o varie de 0 à 50.

wherein the diene system is of Z, Z configuration; Z, E; E, Z or E, E or mixtures of said configurations and wherein: R 2 and R 2, which may be identical or different, denote hydrogen, a C 1 -C 8 alkyl radical; a C1-C8 alkoxy radical; - R3 denotes a COOR5 group; CONR5R6; CN; - R4 denotes a group COOR; CONR5R6; - R5 is hydrogen; [V] oR; C1-C6-alkylene-SO3Y; C1-C6-alkylene-N (R8) 3+ A-; - R6 denotes [V] o -R7; C1-C6-alkylene-SO3U; C1-C6-alkylene-N (R A-) - V is -CH2-CH2-O-, -CH2CH2CH2O-, -CH (CH3) -CH2-O-, A is Cl, Br, l, SO4R9 U denotes hydrogen, Na +, K +, Mg2 +, Ca2 +, Li +, At, -N (R - R, R and R, which are identical or different, denote hydrogen, a linear or branched C1-C8 alkyl radical; 0 to 50.

<Desc / Clms Page number 11>

Les composés de formule (11) encore plus préférentiels sont choisis parmi ceux répondant à la formule (lac) suivante :

The compounds of formula (11) that are even more preferred are chosen from those corresponding to the following formula (lac):

dans laquelle le système diène est de configuration Z, Z ; Z, E ; E, Z ou E, E ou des mélanges desdites configurations et où : 2 - R1 et Rz, identiques ou différents, désignent hydrogène, un radical alkyle en Ci-Cs ; un radical alcoxy en Ci-Cg ; - R3 désigne un groupe COOR5 ; CONS ; CN ; - R4 désigne un groupe COOR ; CONRR ; - R5 désigne hydrogène ; [V]o-R7 ; Ci-C6-alkylène-SO3U ; Ci-C6-alkylène-N (R3+ A- ; - R6désigne [V],-R7 ; Ci-C6-alkylène-SO3U ; Ci-C6-alkylène-N (R AA ; - V désigne un groupe -CHz-CH2-O-, -CH2CH2CH2O-, -CH (CH3) -CH2-O-, - A désigne C !, Br. t, S04R ; - U désigne hydrogène, Na+, K+, Mg, Ca, Li+, At,-N (R - R, R et R identiques ou différents, désignent hydrogène, un radical alkyle en Cl-C3, linéaire ou ramifié ; - o varie de 0 à 50.

wherein the diene system is of Z, Z configuration; Z, E; E, Z or E, E or mixtures of said configurations and wherein: R 2 and R 2, which may be identical or different, denote hydrogen, a Ci-Cs alkyl radical; a C1-C8 alkoxy radical; - R3 denotes a COOR5 group; CONS; CN; - R4 denotes a group COOR; CONRR; - R5 is hydrogen; [V] o-R7; C1-C6-alkylene-SO3U; C1-C6-alkylene-N (R3 + A-) -R6 is [V], -R7; C1-C6-alkylene-SO3U; C1-C6-alkylene-N (R AA; -V is -CH2-CH2- O-, -CH2CH2CH2O-, -CH (CH3) -CH2-O-, A is C, Br, t, SO4R; U is hydrogen, Na +, K +, Mg, Ca, Li +, At, -N ( R - R, R and R, which are identical or different, denote hydrogen, a linear or branched C1-C3 alkyl radical; o varies from 0 to 50.

<Desc / Clms Page number 12>

The compounds of formula (II) that are even more particularly preferred are chosen from the following compounds:

<Desc / Clms Page number 13>

Les composés de formule (11) tells que définis ci-dessus sont connus en eux- mêmes et leurs structures et leurs synthèses sont décrites dans les demandes de brevet EP0967200 et DE19755649 (faisant partie intégrante du contenu de la description).

The compounds of formula (11) as defined above are known per se and their structures and their syntheses are described in patent applications EP0967200 and DE19755649 (forming an integral part of the content of the description).

dans laquelle le système diène est de configuration Z, Z ; Z, E ; E, Z ou E, E ou des mélanges desdites configurations et où : -R1, R2, R3 et I ont les mêmes significations indiquées dans la formule (11)

précédente ; - Y'désigne un groupe-0-ou-NR- - R désigne hydrogène ; un radical alkyle en Cl-C20, linéaire ou ramifié ; un radical alcényle en C2-C1o ; un radical cycloalkyle en Cs-Cio ; un radical Among the preferred 4,4-diarylbutadiene compounds according to the invention, mention may also be made of the oligomers corresponding to the following formula (III):

wherein the diene system is of Z, Z configuration; Z, E; E, Z or E, E or mixtures of said configurations and wherein: -R1, R2, R3 and I have the same meanings indicated in formula (11)

former ; Y 'denotes a group -O-or-NR- - R denotes hydrogen; a linear or branched C1-C20 alkyl radical; a C2-C10 alkenyl radical; a C 5 -C 10 cycloalkyl radical; a radical

<Desc / Clms Page number 14>

bicycloalkyle en C7-Ci ; un radical cycloalcényle en Cs-Cio ; ; un radical bicycloalcényle en Cp-Cio ; un aryle ; un hétéroaryle ; - X'désigne un reste de polyol linéaire ou ramifié, aliphatique ou cycloaliphatique comprenant de 2 à10 groupes hydroxy et de valence q ; la chaîne carbonée dudit reste pouvant être interrompue par un ou plusieurs atomes de souffre ou d'oxygène ; un ou plusieurs groupes imines ; un ou plusieurs alkylimino en C1-C4 ; - 1 varie de 2 à 10.

C7-C1 bicycloalkyl; a C 5 -C 10 cycloalkenyl radical; ; a C 1 -C 10 bicycloalkenyl radical; aryl; a heteroaryl; X 'denotes a linear or branched, aliphatic or cycloaliphatic polyol residue comprising from 2 to 10 hydroxyl groups and of valence q; the carbon chain of said remainder may be interrupted by one or more atoms of sulfur or oxygen; one or more imine groups; one or more C1-C4 alkylimino; - 1 varies from 2 to 10.

Les composés plus préférentiels de formule (III) sont ceux pour lesquels : X is a polyol residue containing from 2 to 10 hydroxyl groups and in particular:

The more preferred compounds of formula (III) are those for which:

<Desc / Clms Page number 15>

2 - R'et R, identiques ou différents, désignent hydrogène, un radical alkyle en Ci-Ci2 ; un radical alcoxy en Ci-Ce ; un substituant hydrosolubilisant choisi parmi un groupe carboxylate, un groupe sulfonate ou un reste ammonium ; - R désigne un groupe COOR5 ; CONR5R ; CN ; un radical cycloalkyle en C3Cio ; un radical bicycloalkyle en CrC1o ; 6 - R5 et R, identiques ou différents, désignent un radical alkyle en Cl-C20, linéaire ou ramifié ; un radical cycloalkyle en Cs-Cio ; un radical bicycloalkyle en C7-C1o ; naphtyle ou phényle éventuellement substitué ; - X'désigne un reste de polyol comprenant de 2 à 6 groupes hydroxy et plus particulièrement de 2 à 4.

R 2 and R 3, which may be identical or different, denote hydrogen, a C 1 -C 12 alkyl radical; a C1-C6 alkoxy radical; a water-solubilising substituent selected from a carboxylate group, a sulfonate group or an ammonium residue; - R denotes a COOR5 group; CONR5R; CN; a C 3 -C 10 cycloalkyl radical; a C 1 -C 20 bicycloalkyl radical; R5 and R, which may be identical or different, denote a linear or branched C1-C20 alkyl radical; a C 5 -C 10 cycloalkyl radical; a C7-C10 bicycloalkyl radical; naphthyl or optionally substituted phenyl; X 'denotes a polyol residue comprising from 2 to 6 hydroxyl groups and more particularly from 2 to 4.

Even more preferred compounds of formula (tut) are those for which: X 'denotes a residue of ethanol or pantaerylthrol.

The compounds of formula (tet) still more particularly preferred are chosen from the following compounds:

<Desc / Clms Page number 16>

Les composés de formule (III) tels que définis ci-dessus sont connus en euxmêmes et leurs structures et leurs synthèses sont décrites dans la demande de brevet EP-A-1008586 (faisant partie intégrante du contenu de la description).

The compounds of formula (III) as defined above are known in themselves and their structures and their syntheses are described in the patent application EP-A-1008586 (forming an integral part of the content of the description).

The compounds 4, 4-dlarylbutadiene according to the invention are present in the composition of the invention at contents which preferably vary from 1% to 10% by weight, relative to the total weight of the composition. The compositions according to the invention The invention may comprise in addition to other complementary organic UV filters active in the UVA and / or UVB (absorbers), water-soluble or fat-soluble or insoluble in the cosmetic solvents commonly used.

demandes US5, 237, 071, US5, 166, 355, GB2303549, DE 197 26 184 et EP893119 ; les polymères filtres et silicones filtres autres que ceux de l'invention tels que ceux décrits notamment dans la demande WO-93/04665 ; les dimères dérivés d'a-alkylstyrène tels que ceux décrits dans la demande de brevet DE19855649. The complementary organic UV filters are in particular chosen from anthranilates; cinnamic derivatives; salicylic derivatives, camphor derivatives other than p-methyl-benzylidene camphor; triazine derivatives such as those described in patent applications US 4367390, EP863145, EP517104, EP570838, EP796851, EP775698, EP878469 and EP933376; benzophenone derivatives; derivatives of P, P'-diphenylacrylate, benzotriazol derivatives; benzalmalonate derivatives; benzimidazole derivatives; imadazolines; bis-benzoazolyl derivatives as described in patents EP669323 and US 2,463,264; p-aminobenzoic acid derivatives (PABA); methylene bis (hydroxyphenyl benzotriazole) derivatives as described in

applications US5, 237, 071, US5, 166, 355, GB2303549, DE 197 26 184 and EP893119; filter polymers and silicone filters other than those of the invention such as those described in particular in the application WO-93/04665; dimers derived from α-alkylstyrene such as those described in patent application DE19855649.

As examples of additional organic screening agents active in UV-A and / or UV-B, the above-mentioned INCI names may be mentioned:

<Desc / Clms Page number 17>

- TEA Salicylate, vendu sous le nom NEO HELIOPAN TS par HAARMANN et REIMER, Dérivés cinnamiques : - Ethylhexyl Methoxycinnamate vendu notamment sous le nom commercial PARSOL MCX par HOFFMANN LA ROCHE, - Isopropyl Methoxy cinnamate, Isoamyl Methoxy cinnamate vendu sous le nom commercial NEO HELIOPAN
E 1000 par HAARMANN et REIMER, Cinoxate, - DEA Methoxycinnamate, --DisopropylMethylcinnamate,

- Glyceryl Ethylhexanoate Dlmethoxycinnamate Dérivés de ss, 6'-diphénvtacrytate : - Octocrylene vendu notamment sous le nom commercial UVINUL N539 par
BASF, - Etocrylene, vendu notamment sous le nom commercial UVINUL N35 par
BASF, Dérivés de la benzophénone : - Benzophenone-1 vendu sous le nom commercial UVINUL 400 par BASF, - Benzophenone-2 vendu sous le nom commercial UVINUL D50 par BASF - Benzophenone-3 ou Oxybenzone, vendu sous le nom commercial UVINUL
M40 par BASF, - Benzophenone-4 vendu sous le nom commercial UVINUL MS40 par
BASF, - Benzophenone-5 - Benzophenone-6 vendu sous le nom commercial HELISORB 11 par
NORQUAY - Benzophenone-8 vendu sous le nom commercial SPECTRA-SORB UV-24
PAR AMERICAN CYANAMID - Benzophenone-9 vendu sous le nom commercial UVINUL DS-49 par BASF, - Benzophenone-12 Derivatives of para-aminobenzoic acid: PABA, Ethyl PABA, Ethyl Dihydroxypropyl PABA, Ethylhexyl Dlmethyl PABA sold in particular under the name ESCALOL 507 by ISP, Glyceryl PABA, PEG-25 PABA sold under the name UVINUL P25. by BASF, Salicylic derivatives: - Homosalate sold under the name EUSOLEX HMS by RONA / EM
INDUSTRIES, - Ethylhexyl Salicylate sold under the name NEO HELIOPAN OS by
HAARMANN and REIMER, - Dtpropytenegtycot Saticytate sold under the name DIPSAL by SCHER,

TEA Salicylate, sold under the name NEO HELIOPAN TS by HAARMANN and REIMER, cinnamic derivatives: Ethylhexyl Methoxycinnamate sold in particular under the trade name PARSOL MCX by Hoffmann La Roche, Isopropyl Methoxy Cinnamate, Isoamyl Methoxy Cinnamate sold under the trade name NEO HELIOPAN
E 1000 by HAARMANN and REIMER, Cinoxate, - DEA Methoxycinnamate, --DisopropylMethylcinnamate,

- Glyceryl Ethylhexanoate Dlmethoxycinnamate Derivatives of ss, 6'-diphenvtacrytate: - Octocrylene sold in particular under the trade name UVINUL N539 by
BASF, Etocrylene, sold in particular under the trade name UVINUL N35 by
BASF, Derivatives of benzophenone: Benzophenone-1 sold under the trade name UVINUL 400 by BASF; Benzophenone-2 sold under the trade name UVINUL D50 by BASF-Benzophenone-3 or Oxybenzone, sold under the trade name Uvinul
M40 by BASF, - Benzophenone-4 sold under the trade name UVINUL MS40 by
BASF, - Benzophenone-5 - Benzophenone-6 sold under the trade name HELISORB 11 by
NORQUAY - Benzophenone-8 sold under the trade name SPECTRA-SORB UV-24
BY AMERICAN CYANAMID - Benzophenone-9 sold under the trade name UVINUL DS-49 by BASF, - Benzophenone-12

<Desc / Clms Page number 18>

Dérivé du benzylidène camphre : - 3-benzyliden camphor fabriqué sous le nom MEXORYL SD par CHIMEX, - Benzylidene Camphor Sulfonic Acid fabriqué sous le nom MEXORYL SL par CHIMEX, - Camphor Benzalkonium Methosulfate fabriqué sous le nom MEXORYL SO par CHIMEX, --Terephthalylidene Dicamphor Sulfonic Acid fabriqué sous le nom MEXORYL
SX par CHIMEX, - Polyacrylamidomethyl Benzylidene Camphor fabriqué sous le nom MEXORYL SW)) par CHIMEX, Dérivés de benzimidazole : - Phenylbenzimidazole Sulfonic Acid vendu notamment sous le nom commercial EUSOLEX 232 par MERCK, - Benztmtdazitate vendu sous le nom commercial commercial NEO HELIOPAN AP par HAARMANN et REIMER, Dérivés de la triazine : - Anisotriazine vendu sous le nom commercial TINOSORB S par CIBA
SPECIALTY CHEMICALS, - Ethylhexyl triazone vendu notamment sous le nom commercial UVINUL Tl 50 par BASF,

- Diethylhexyl Butamido Triazone vendu sous le nom commercial UVASORB HEB par par SIGMA 3V, Dérivés du phenyl benzotriazol : - Drometrizole Trisiloxane vendu sous le nom SILATRIZOLE par RHODIA
CHIMIE, - Methylène bis-Benzotriazolyl Tetramethylbutylphénol, vendu sous forme solide sous le nom commercial MIXXIM BB/100 par FAIRMOUNT CHEMICAL ou sous forme micronisé en dispersion aqueuse sous le nom commercial TINOSORB M par CIBA SPECIALTY CHEMICALS, Dérivés anthraniliques : - Menthyl anthranilate vendu sous le nom commercial commercial NEO
HELIOPAN MA par HAARMANN et REIMER, Dérivés d'imidazolines : - Ethylhexyl Dimethoxybenzylidene Dioxoimdazoline Propionate, Dérivés de benzalmalonate : - Polyorganosiloxane à fonction benzalmalonate vendu sous la dénomination commerciale PARSOL SLX par HOFFMANN LA ROCHE et leurs mélanges.

Derivative of benzylidene camphor: - 3-benzyliden camphor manufactured under the name MEXORYL SD by CHIMEX, - Benzylidene Camphor Sulfonic Acid manufactured under the name MEXORYL SL by CHIMEX, - Camphor Benzalkonium Methosulfate manufactured under the name MEXORYL SO by CHIMEX, --Terephthalylidene Dicamphor Sulfonic Acid manufactured under the name MEXORYL
SX by CHIMEX, - Polyacrylamidomethyl Benzylidene Camphor manufactured under the name MEXORYL SW)) by CHIMEX, Benzimidazole derivatives: - Phenylbenzimidazole Sulfonic Acid sold in particular under the trade name EUSOLEX 232 by MERCK, - Benztmtdazitate sold under the trade name NEO HELIOPAN AP by HAARMANN and REIMER, Triazine derivatives: - Anisotriazine sold under the trade name TINOSORB S by CIBA
SPECIALTY CHEMICALS, - Ethylhexyl triazone sold in particular under the trade name UVINUL Tl 50 by BASF,

- Diethylhexyl Butamido Triazone sold under the trade name UVASORB HEB by SIGMA 3V, Derivatives of phenyl benzotriazol: - Drometrizole Trisiloxane sold under the name Silatriazole by Rhodia
CHEMISTRY, - Methylene bis-Benzotriazolyl Tetramethylbutylphenol, sold in solid form under the trade name MIXXIM BB / 100 by FAIRMOUNT CHEMICAL or in micronized form in aqueous dispersion under the trade name TINOSORB M by CIBA SPECIALTY CHEMICALS, Anthranilic derivatives: - Menthyl anthranilate sold under the trade name NEO
HELIOPAN MA by HAARMANN and REIMER, Imidazoline derivatives: Ethylhexyl Dimethoxybenzylidene Dioxoimdazoline Propionate, Derivatives of benzalmalonate: Polyorganosiloxane containing benzalmalonate function sold under the trade name PARSOL SLX by HOFFMANN LA ROCHE and their mixtures.

Soluble organic UV filters which are more particularly preferred are chosen from the following compounds: ethylhexyl salicylate, ethylhexyl methoxycinnamate, octocrylene,

<Desc / Clms Page number 19>

- Phenylbenzimidazole Sulfonic Acid, - Benzophenone-3, -Benzophenone-4, - Benzophenone-5, 4-Methylbenzylidene camphor, - Benzimtdazitate, - Anisotriazine, Ethylhexyl triazone,

- Diethythexyt Butamido Triazone, - Methylène bis-Benzotriazolyl Tetramethylbutylphénol et leurs mélanges.

Phenylbenzimidazole Sulfonic Acid, Benzophenone-3-Benzophenone-4-Benzophenone-5,4-Methylbenzylidene camphor, Benzimedazazitate, Anisotriazine, Ethylhexyl triazone,

Diethylhexyt Butamido Triazone, Methylene bis-Benzotriazolyl Tetramethylbutylphenol and mixtures thereof.

The cosmetic compositions according to the invention may also contain pigments or even nanopigments (average size of the primary particles: generally between 5 nm and 100 nm, preferably between 10 nm and 50 nm) of metal oxides, whether or not coated, such as examples of nanopigments of titanium oxide (amorphous or crystallized rutile form and / or anatase), iron, zinc, zirconium or cerium which are all UV photoprotective agents well known per se. Conventional coating agents are, moreover, alumina and / or aluminum stearate. Such nanopigments of metal oxides, coated or uncoated, are in particular described in patent applications EP-A-0518772 and EP-A-0518773.

The compositions according to the invention may also contain agents for tanning and / or artificial browning of the skin (self-tanning agents), such as, for example, dihydroxyacetone (DHA).

The compositions of the invention may furthermore comprise conventional cosmetic adjuvants chosen in particular from fatty substances, organic solvents, ionic or nonionic thickeners, softeners, antioxidants, anti-free radical agents, opacifiers, stabilizers, emollients, silicones, α-hydroxy acids, anti-foam agents, moisturizers, vitamins, insect repellents, fragrances, preservatives, surfactants, anti-inflammatories, substance P antagonists, fillers, polymers, propellants, alkalinizing or acidifying agents, dyes or any other ingredient usually used in cosmetics, in particular for the manufacture of sunscreen compositions in the form of emulsions.

The fatty substances may be an oil or a wax or mixtures thereof, and they also include fatty acids, fatty alcohols and fatty acid esters. The oils may be chosen from animal, vegetable, mineral or synthetic oils and in particular from petrolatum oil, paraffin oil, silicone oils, which may or may not be volatile, isoparaffins, polyolefins, fluorinated oils and the like. perfluorinated. Similarly, the waxes can be chosen from animal, fossil, vegetable, mineral or synthetic waxes known per se.

Among the organic solvents, mention may be made of lower alcohols and polyols.

<Desc / Clms Page number 20>

Of course, those skilled in the art will take care to choose this or these optional additional compounds and / or their amounts in such a way that the advantageous properties, in particular the synergy of the protective factors, intrinsically attached to the compositions according to the invention are not, or not substantially, impaired by the addition or additions envisaged.

The compositions of the invention may be prepared according to the techniques well known to those skilled in the art, in particular those intended for the preparation of oil-in-water or water-in-oil type emulsions.

These compositions may be in particular in the form of an emulsion, simple or complex (O / W, W / O, O / W / H or W / O / W) such as cream, milk, gel or gel cream, powder, solid stick and optionally be packaged in aerosol and be in the form of foam or spray.

In the case of an emulsion, the aqueous phase thereof may comprise a nonionic vesicle dispersion prepared according to known methods (Bangham, Standish and Watkins, J. Mol Biol 13,238 (1965), FR2315991 and FR2416008).

The cosmetic composition of the invention can be used as a composition for protecting the human epidermis or the hair against ultraviolet rays, as an antisolar composition or as a makeup product.

When the cosmetic composition according to the invention is used for the protection of the human epidermis against UV rays, or as an antisolar composition, it may be in the form of a suspension or dispersion in solvents or fatty substances, in the form of non-ionic vesicular dispersion or in the form of an emulsion, preferably of the oil-in-water type, such as a cream or a milk, in the form of an ointment, a gel, a cream gel, a solid stick or a powder, stick, aerosol foam or spray.

When the cosmetic composition according to the invention is used for protecting the hair against UV rays, it may be in the form of a shampoo, a lotion, a gel, an emulsion or a nonionic vesicle dispersion and may constitute, for example, a composition. rinsing, applying before or after shampooing, before or after coloring or bleaching, before, during or after permanent or straightening, a styling or treatment lotion or gel, a lotion or a gel for blow-drying or setting, a composition of permanent or straightening, coloring or discoloration of hair.

 When the composition is used as a makeup product for eyelashes, eyebrows or skin, such as epidermis cream, foundation, lipstick stick, eyeshadow, blush, mascara or liner also called "eyeliner", it can be in solid or pasty, anhydrous or aqueous, such as oil in water or water in oil emulsions, nonionic vesicular dispersions or suspensions.

As an indication, for the antisolar formulations according to the invention which have an oil-in-water emulsion type support, the aqueous phase

<Desc / Clms Page number 21>

 (Comprising in particular the hydrophilic filters) generally represents from 50 to 95% by weight, preferably from 70 to 90% by weight, relative to the overall formulation, the oily phase (including in particular the lipophilic filters) from 5 to 50% by weight, preferably from 10 to 30% by weight, relative to the overall formulation, and the (co) emulsifier (s) from 0.5 to 20% by weight, preferably from 2 to 10% by weight, based on the overall formulation.

As indicated at the beginning of the description, an object of the invention is the use of a composition as defined above for the manufacture of a cosmetic or dermatological composition intended for the protection of the skin and / or the hair against radiation ultraviolet, especially solar radiation.

Concrete but non-limiting examples illustrating the invention will now be given

<Tb>
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<Tb>

<Desc / Clms Page number 22>

<Tb>
<tb> COMPOSITION <SEP> EX <SEP> 2
<tb><SEP> mixture of <SEP> cetylstearyl alcohol <SEP> and <SEP> of alcohol <SEP> cetylstearyl alcohol <SEP> 7
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<Tb>
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<tb> (DOW <SEP> CORNING <SEP> 200 <SEP> FLUID <SEP> - <SEP> DOW <SEP> CORNING)
<tb> Benzoate <SEP> lcools <SEP> in <SEP> C12 / C15 <SEP> 20
<tb> (WtTCONOLTN-W) <SEP> TCO)
<tb> Triethanolamine <SEP> 0.5
<tb> Drometrizole <SEP> Trisiloxane <SEP> 6
<tb> (SILATRIZOLE, <SEP> RHODIA <SEP> CHEMISTRY)
<tb> Compound <SEP> of <SEP> formula <SEP> (11) <SEP> 8
<tb> Oxybenzone, <SEP> 10
<tb> (UVINUL <SEP> M40, <SEP> BASF)
<tb> Glycerin <SEP> 4
<tb> Triethanolamine <SEP> 0.3
<tb> polyacrylic acid <SEP><SEP> 0.4
<tb> (SYNTHALEN <SEP> K-3V)
<tb> Conservatives <SEP> qs
<tb> Water <SEP> demineralizedqsp100g
<Tb>

<Desc / Clms Page number 23>

<Tb>
<tb> COMPOSITION <SEP> EX <SEP> 4
<tb><SEP> mixture of <SEP> cetylstearyl alcohol <SEP> and <SEP> of alcohol <SEP> cetylstearyl alcohol <SEP> 7
<tb> oxyethylenated <SEP> (33 <SEP> OE) <SEP> 80/20 <SEP> (SINNOWAX <SEP> AO-HENKEL)
<tb><SEP> Blend of <SEP> Mono <SEP> and <SEP> Distearate <SEP> of <SEP> Glycerol <SEP> 2
<tb> (CERASYNT <SEP> SD-V <SEP> ISP)
<tb> Alcohol <SEP> Cetyl <SEP> 1.5
<tb> Polydimethyl <SEP> slloxane <SEP> 1. <SEP> 5
<tb> (DOW <SEP> CORNING <SEP> 200 <SEP> FLUID <SEP> - <SEP> DOW <SEP> CORNING)
<tb> Oil <SEP> of <SEP> Vaseline <SEP> 15
<tb> Ethylhexyl <SEP> Methoxycinnamate <SEP> 7
<tb> (PARSOL <SEP> MCX <SEP> HOFFMANN <SEP> THE <SEP> ROCK)
<tb> Compound <SEP> of <SEP> formula <SEP> (13) <SEP> 6
<tb> Drometnzole <SEP> Trisiloxane <SEP> 6
<tb> (SILATRIZOLE, <SEP> RHODIA <SEP> CHEMISTRY)
<tb> Glycerine <SEP> 15
<tb> Conservatives <SEP> qs
<tb> Demineralized water <SEP><SEP> qsp <SEP> 100g
<Tb>

<Tb>
<tb> COMPOSITION <SEP> EX <SEP> 5
<tb> Mixture <SEP> mono <SEP> / <SEP> distearate <SEP> of <SEP> glycerol / stearate <SEP> from <SEP> polyethylene <SEP> 2
<tb> glycol <SEP> (100 <SE> OE)
<tb> (ARLACEL <SEP> 165 <SEP> FL <SEP> - <SEP> HERE)
<tb> Alcohol <SEP> stearyl alcohol <SEP> 1
<tb> (LANETTE <SEP> 18-HENKEL)
<tb><SEP> Stearic acid <SEP> oil <SEP> of <SEP> palm <SEP> 2.5
<tb> (STEARIN <SEP> TP <SEP> - <SEP> STEARINERY <SEP> DUBOIS)
<tb> Polydimethylsiloxane <SEP> 0.5
<tb> (DOW <SEP> CORNING <SEP> 200 <SEP> FLUID <SEP> - <SEP> DOW <SEP> CORNING)
<tb> Benzoate <SEP> of alcohols <SEP> in <SEP> C12 / C15 <SEP> 20
<tb> (WITCONOL <SEP> TCONOL <SEP> TN <SEP> - <SEP> WITCO)
<tb> Triethanolamine <SEP> 0. <SEP> 5
<tb> Drometrizole <SEP> Trisiloxane <SEP> 5
<tb> (SILATRIZOLE, <SEP> RHODIA <SEP> CHEMISTRY)
<tb> Compound <SEP> of <SEP> formula <SEP> (15) <SEP> 5
<tb> Glycerin <SEP> 4
<tb> Triethanolamine <SEP> 0.3
<tb> polyacrylic acid <SEP><SEP> 0.4
<tb> (SYNTHALEN <SEP> K-3V)
<tb> Conservatives <SEP> qs
<tb> Demineralized <SEP> water <SEP> qsp <SEP> 100 <SEP> g
<Tb>

<Desc / Clms Page number 24>

<Tb>
<tb> COMPOSITION <SEP> EX <SEP> 6
<tb> Mixture <SEP> mono / distearate <SEP> of <SEP> glycerol / stearate <SEP> from <SEP> polyethylene <SEP> 2
<tb> glycol <SEP> (100 <SE> OE)
<tb> (ARLACEL <SEP> 165 <SEP> FL <SEP> - <SEP> HERE)
<tb> Alcohol <SEP> stearylfc <SEP> 1
<tb> (LANETTE <SEP> 18 <SEP> - <SEP> HENKEL)
<tb><SEP> Stearic acid <SEP> oil <SEP> of <SEP> palm <SEP> 2.5
<tb> (STEARINE <SEP> TP <SEP> - <SEP> STEARINERY <SEP> DUBOIS)
<tb> Poly <SEP> dimethylsiloxane <SEP> 05
<tb> (DOW <SEP> CORNING <SEP> 200 <SEP> FLUID <SEP> - <SEP> DOW <SEP> CORNING)
<tb> Benzoate <SEP> of alcohols <SEP> in <SEP> C12 / C15 <SEP> 20
<tb> (WITCONOL <SEP> TN <SEP> -WITCO)
<tb> Triethanolamine <SEP> 05
<tb> Ethylhexyl <SEP> Methoxycinnamate <SEP> 7
<tb> (PARSOL <SEP> MCX <SEP> HOFFMANN <SEP> THE <SEP> ROCK)
<tb> Drometnzole <SEP> Trisiloxane <SEP> 5
<tb> (SILATRIZOLE, <SEP> RHOIDA <SEP> CHEMISTRY)
<tb> Compound <SEP> of <SEP> Formula <SEP> (8) <SEP> 8
<tb> Glycerin <SEP> 4
<tb> Triethanolamine <SEP> 0.3
<tb> polyacrylic acid <SEP><SEP> 0.4
<tb> (SYNTHALEN <SEP> K-3V)
<tb> Conservatives <SEP> qs
<tb> Demineralized <SEP> water <SEP> qsp <SEP> 100 <SEP> g
<Tb>

Claims (25)

1. Cosmetic composition, in particular antisolar, characterized in that it comprises, in a cosmetically acceptable support: (i) from 0.5 to 15% by weight of at least one benzotriazol-functional silicic acid derivative as a first filter; (ii) from 0.5 to 15% by weight of at least one 4,4-diarylbutadiene compound as a second filter; said first and second filters being present in said composition in a proportion producing a synergistic activity at the conferred sun protection levels. 2. Composition according to claim 1, wherein the benzotriazole-functional silicon derivative is chosen from silanes and / or benzotriazol-functional polyorganosiloxanes comprising at least one unit of formula (1) below: 0 (3-a) / 2 Si (R7) aG (1) in which: - R7 represents an optionally halogenated C1-C10 alkyl radical or a phenyl radical or a trimethylsilyloxy radical, - a is an integer selected from 0 and 3 inclusive, and the symbol G denotes a monovalent radical directly attached to a silicon atom, and which corresponds to the following formula (2):

 in which: Y, which are identical or different, are chosen from C1-C8 alkyl radicals, halogens and C1-C4 alkoxy radicals, it being understood that, in the latter case, two adjacent Y's of one and the same aromatic nucleus may together forming an alkylidene dioxy group in which the alkylidene group contains from 1 to 2 carbon atoms, - X represents 0 or NH, - Z represents hydrogen or a C1-C4 alkyl radical, - n is an integer between 0 and 3 inclusive, - m is 0 or 1, - p represents an integer between 1 and 10, inclusive. 3. Composition according to claim 1 or 2, characterized in that the benzotriazol-functional silicone derivative corresponds to one of the following formulas (5) or (6): <Desc / Clms Page number 26>

 or

 in which: R7, which are identical or different, are chosen from C1-C10 alkyl, phenyl, trifluor-3,3,3-propyl and trimethylsilyloxy radicals, at least 80% by number of the R7 radicals being methyl, -D, identical; or different are selected from radicals R7 and radical G, - r is an integer from 0 to 50 inclusive, and s is an integer from 0 to 20 inclusive, and if s = 0, at least one of the two symbols D denotes G, - u is an integer between 1 and 6 inclusive, and t is an integer between 0 and 10 inclusive, provided that t + u is equal to or greater than 3, - and the symbol G has the formula (2) defined in claim 2. 4. Composition according to Claim 3, characterized in that the benzotriazol-functional silicon derivative has the following formula (7):

<Desc / Clms Page number 27>

 with 0 <r 10, 1s 10, and where E represents the divalent radical:

 5. Composition according to Claim 4, characterized in that the benzotriazole-functional silicon derivative is Drometzole Trisiloxane of the following formula:

 6. Composition according to any one of claims 1 to 5, characterized in that the benzotriazole-functional silicon derivatives are present in a content ranging from 1% to 10% by weight, relative to the total weight of the composition. 7. The composition of any one of claims 1 to 6, wherein the 4,4diarylbutadiene compound has the following formula (II):

 wherein the diene system is of Z, Z configuration; Z, E; E, Z or E, E or

 mixtures of said configurations and wherein: - R 'and R, which are identical or different, denote hydrogen, a linear or branched C1-C20 alkyl radical; a C2-C10 alkenyl radical; a C1-C12 alkoxy radical; a C 5 -C 10 cycloalkyl radical; a C 3 -C 10 cycloalkenyl radical; a linear or branched C1-C20 alkoxycarbonyl radical; a linear or branched C 1 -C 12 monoalkylamino radical; a linear or branched C 1 -C 12 dialkylamino radical; aryl; a heteroaryl or a water-solubilising substituent selected from a carboxylate group, a sulfonate group or an ammonium residue; <Desc / Clms Page number 28>

 - R3 denotes a COOR5 group; COR; CONR5R6; CN; a linear or branched C1-C20 alkyl radical; a C2-C10 alkenyl radical; a C3-C10 cycloalkyl radical; a C 1 -C 10 bicycloalkyl radical; a C 3 -C 10 cycloalkenyl radical; a C7-C10 bicycloalkenyl radical; a C6-C18 aryl; a C3-C7 heteroaryl; -R4 denotes a COOR group; COR 6; CONR5R6; CN; a linear or branched C 1 -C 20 alkyl radical; a C2-C10 alkenyl radical; a C 3 -C 10 cycloalkyl radical; a C7-C10 bicycloalkyl radical; a C 3 -C 10 cycloalkenyl radical; a C7-C10 bicycloalkenyl radical; aryl; a heteroaryl;

 - R5 and R, identical or different, denote hydrogen; [V0-R, d-Ce-aikytene-SOsU; C1-C6-alkylene-PO3U; C1-C6-alkylene-N (R A-) linear or branched C1-C20 alkyl radical, C2-C10 alkenyl radical, C3-C10 cycloalkyl radical, C7-C10 bicycloalkyl radical; C 1 -C 10 cycloalkenyl; a C 1 -C 10 bicycloalkenyl radical; an aryl;

 heteroaryl; V represents a group -CH2-CH2-W-, -CH2CH2CH2W-, -CH (CH3) -CH2-W-, -CH2-CH2-CH2-CH2-W-CH2-CH (CH2CH3) -W- ; A is CI, Br, 1, SO4R9; U denotes hydrogen, Na +, K +, Mg2 +, Ca, Li ', A! , -N (RS - W denotes 0 or NH; R7 and R, which are identical or different, denote hydrogen, a linear or branched C1-C6 alkyl radical, a linear or branched C2-C6 alkenyl radical; an acyl radical; linear or branched C1-C6-R9 denotes hydrogen, a linear or branched C1-C6 alkyl radical, a C2-C6 alkenyl radical, ranging from 1 to 3, and ranging from 0 to 150. 8. Composition according to claim 7, wherein the compound of formula (II) is chosen from those of formula (IIa) below:

 wherein the diene system is of Z, Z configuration; Z, E; E, Z or E, E or mixtures of said configurations and wherein: - R1 and R2, identical or different, denote hydrogen, a C1-C6 alkyl radical; a C1-C8 alkoxy radical; a water-solubilising substituent selected from a carboxylate group, a sulfonate group or an ammonium residue;

 - R denotes a COOR5 group; CONR; CN; - R4 denotes a COOR6 group; 7CONS; - R5 is hydrogen; Mo-R7; C1-C10-alkylene-SO3U; C1-C6-atkytene-N (R8) 3+ A-; X - R "is Mo-R7; d-Ce-alkylene-SO3U; C1-C6-alkylene-N (Rsh + A-; <Desc / Clms Page number 29>

 V is -CH2-CH2-O-, -CH2CH2CH2O-, -CH (CH3) -CH2-O-, A is CI, Br, 1, SO4R9; Hydrogen, Na +, K +, Mg 2 +, Ca, Li +, A-N (R 8) 4 + - R 7, R and R 9, which may be identical or different, denote hydrogen, a linear or branched C 1 -C 3 alkyl radical; - I varies from 1 to 3 - o varies from 0 to 50 9 Composition according to claim 8, wherein the compound of formula (II) is chosen from those of formula formula (IIb) below:

 wherein the diene system is of Z, Z configuration; Z, E; E, Z or E, E or mixtures of said configurations and wherein: R 'and R2, identical or different, denote hydrogen, an alkyl radical in

 C 1 -C 8; a C1-C8 alkoxy radical; R3 denotes a COOR group; CONR; CN; - R4 denotes a COOR6 group; CONR5R6; - R5 is hydrogen; [V] o-R7; C1-C6-alkylene-SO3U; C1-C6-alkylene-N (R8) 3+ A-; - R "is Mo-R7; Cl-C6-alkylene-SO3U; C1-C6-alkylene-N (RA '); - V is -CH2-CH2-O-, -CH2CH2CH2O-, -CH (CH3) - CH 2 -O-, A denotes Cl, Br, l, SO 4 R 9; U denotes hydrogen, Na +, K +, Mg, Ca 2 +, Li +, Al, -N (R-R 7, R and R 9, which may be identical or different, denote hydrogen, a linear or branched C 1 -C 3 alkyl radical; o varies from 0 to 50. 10. Composition according to claim 9, wherein the compound of formula (II) is chosen from those corresponding to the following formula (ltc): <Desc / Clms Page number 30>

 wherein the diene system is of Z, Z configuration; Z, E; E, Z or E, E or mixtures of said configurations and wherein: - R1 and Rz, identical or different, denote hydrogen, a Ci-Cs alkyl radical; a C1-C8 alkoxy radical; - R3 denotes a COOR5 group; CONR5R6; CN; - R4 denotes a COUR6 group; CONR5R6; - R5 is hydrogen; [V] o-R; Ce-aikytene-SOgU; C1-C6-alkylene-N (RA1) -R6 denotes [V] o -R7; d-Ce-atkyiene-SOsU; C1-C6-alkylene-N (R3 AA; -V denotes a -CH2-CH2-group; O -, - CH 2 CH 2 CH 2 O -, - CH (CH 3) -CH 2 -O-, A denotes Cl, Br, l, SO 4 R, - U denotes hydrogen, Na +, K +, Mg 2+, Ca 2+, Li +, At.-N (R R 7, R and R 9, which may be identical or different, denote hydrogen, a linear or branched C 1 -C 3 alkyl radical; <Desc / Clms Page number 31>  11. Composition according to claim 9 or 10, wherein the 4,4diarylbutadiene compound is chosen from the following compounds:

<Desc / Clms Page number 32>

 The composition of claim 1 wherein the 4,4-diarylbutadiene compound is an oligomer of the following formula (III):

 wherein the diene system is of Z, Z configuration; Z, E; E, Z or E, E-or mixtures of said configurations and wherein: - R1, R2 R3 and I have the same meanings given in formula (II) in claim 7; Y 'denotes a group -O- or -NR' - - R10 denotes hydrogen; a linear or branched C 1 -C 20 alkyl radical; a C2-C10 alkenyl radical; a C 5 -C 10 cycloalkyl radical; a bicycloalkyl radical C 1 -C 10; a C 3 -C 10 cycloalkenyl radical; a C 1 -C 10 bicycloalkenyl radical; aryl; a heteroaryl; X 'denotes a linear or branched, aliphatic or cycloaliphatic polyol residue comprising from 2 to 10 hydroxyl groups and of valence q; the carbon chain of said remainder may be interrupted by one or more atoms of sulfur or oxygen; one or more imine groups or one or more C 1-4 alkylimino groups; - q varies from 2 to 10. The composition of claim 12, wherein the compound of formula (III) is

 chosen from those for which: R 2 and R 2, which are identical or different, denote hydrogen, a C 1 -C 12 alkyl radical; a C1-C8 alkoxy radical; a water-solubilising substituent selected from a carboxylate group, a sulfonate group or an ammonium residue 5. 5 6; - R denotes a group COURT, CONR R CN; a C 3 -C 10 cycloalkyl radical; a bicycloalkyl radical C 1 -C 10; <Desc / Clms Page number 33>

 - R5 and R6, identical or different, denote a linear or branched C1-C20 alkyl radical; a C3-C10 cycloalkyl radical; a C 1 -C 10 bicycloalkyl radical; naphthyl or optionally substituted phenyl; X 'denotes a polyol residue comprising from 2 to 6 hydroxyl groups and more particularly from 2 to 4. 14. Composition according to claim 13, wherein the compound of formula (III) is chosen from those for which: X 'denotes a residue of ethanol or pentaerythrol. 15. The composition according to claim 14, wherein the compound of formula (tut) is chosen from the following compounds:

<Desc / Clms Page number 34>

 16. Composition according to any one of claims 1 to 15, characterized in that the compound 4, 4-diarylbutadiene is present at levels ranging from 1 to 10%, by weight, always relative to the total weight of the composition . 17. Composition according to any one of claims 1 to 16, characterized in that it contains in addition to other organic filters active in the UV-A and / or UV-B. 18. Composition according to claim 17, wherein the additional organic UV screening agent (s) is (are) chosen from anthranilates; cinnamic derivatives; salicylic derivatives, camphor derivatives other than p-methyl benzylidene camphor; triazine derivatives; benzophenone derivatives; the derivatives of p. p-diphenylacrylate, benzotriazol derivatives; benzalmalonate derivatives; benzimidazole derivatives; imadazolines; bis-benzoazolyl derivatives; p-aminobenzoic acid derivatives (PABA); methylene bis (hydroxyphenyl benzotriazole) derivatives; filter polymers and silicone filters other than the silicon derivatives of benzotriazol; dimers derived from α-alkylstyrene. 19. Composition according to Claim 18, characterized in that the organic UV screening agent (s) is (are) chosen from the following compounds: ethylhexyl salicylate, ethylhexyl methoxycinnamate, octocrylene, phenylbenzimidazole sulphonic acid, benzophenone-3, benzophenone 4, Benzophenone-5, 4-Methylbenzylidene camphor, Benzimidazilate, Anisotriazine, <Desc / Clms Page number 35>

 Ethylhexyl triazone, Diethythexyt Butamido Triazone, Methylene bis-Benzotriazolyl Tetramethylbutylphenol and mixtures thereof. 20. Composition according to any one of claims 1 to 19, characterized in that it further comprises pigments or nanopigments of metal oxides, coated or uncoated. 21. The composition as claimed in claim 20, characterized in that said pigments or nanopigments are chosen from titanium, zinc, iron, zirconium and cerium oxides and mixtures thereof, coated or uncoated. 22. Composition according to any one of claims 1 to 21, characterized in that it further comprises at least one agent for tanning and / or artificial browning of the skin. 23. Composition according to any one of claims 1 to 22, characterized in that it further comprises at least one adjuvant selected from fatty substances, organic solvents, ionic or nonionic thickeners, softeners, antioxidants anti-free radical agents, opacifiers, stabilizers, emollients, silicones, α-hydroxy acids, anti-foam agents, moisturizers, vitamins, anti-inflammatory agents,

 insects, perfumes, preservatives, surfactants, anti-inflammatories, substance P antagonists, fillers, polymers, propellants, basifying or acidifying agents, dyes. 24. Composition according to any one of claims 1 to 23, characterized in that it is a protective composition of the human epidermis or an antisolar composition and that it is in the form of a non-ionic vesicle dispersion, an emulsion, in particular an oil-in-water emulsion, a cream, a milk, a gel, a cream gel, a suspension , a dispersion, a powder, a solid stick, a foam or a spray. 25. A composition according to any one of claims 1 to 23, characterized in that it is a makeup composition of eyelashes, eyebrows or skin and that it is in solid or pasty form. , anhydrous or aqueous, an emulsion, a suspension or a dispersion. 26. A composition according to any one of claims 1 to 23, characterized in that it is a composition for protecting the hair against ultraviolet rays and is in the form of a shampoo, lotion, gel, emulsion, non-ionic vesicular dispersion. 27. Use of a composition as defined in claims 1 to 23 for the manufacture of cosmetic or dermatological compositions for the protection of the skin and / or the hair against ultraviolet radiation, in particular solar radiation. <Desc / Clms Page number 36> 28. Use of a compound 4, 4-diarylbutadiene as defined in the preceding claims for the manufacture of cosmetic or dermatological compositions for the protection of the skin and / or the hair against ultraviolet radiation, in particular the solar radiation comprising at least one filter of the silicic derivative type of benzotriazol as defined in the preceding claims, for the purpose of producing a synergistic effect at the level of the sun protection indices conferred.