WO2016166345A1

WO2016166345A1 - Composition made from trans-resveratrol or from a trans-resveratrol derivative

Info

Publication number: WO2016166345A1
Application number: PCT/EP2016/058452
Authority: WO
Inventors: Stéphanie Cheilian; Sandrine THEROUIN-KOELY; Catherine SOCROUN-METIVIER
Original assignee: L'oreal
Priority date: 2015-04-15
Filing date: 2016-04-15
Publication date: 2016-10-20
Also published as: FR3034987B1; EP3283047A1; FR3034987A1; CN107787225A

Abstract

The invention relates to a cosmetic or dermatological composition comprising, in a physiologically acceptable medium, at least trans-resveratrol and/or at least one trans-resveratrol derivative, and a filtering system comprising at least one amino-substituted 2-hydroxybenzophenone long UVA filter and at least one additional UV filter chosen from water-soluble organic UVA filters, liposoluble mixed organic UVA-UVB filters, mineral filters and/or mixtures thereof. The invention also relates to a use of a filtering system comprising at least one amino-substituted 2-hydroxybenzophenone long UVA filter and at least one additional UV filter chosen from water-soluble organic UVA filters, water-soluble organic UVB filters, mineral filters and/or mixtures thereof in order to stabilise, and in particular to photostabilise, a composition comprising trans-resveratrol and/or at least one trans-resveratrol derivative.

Description

Composition based on fmra.s'-resveratrol or a derivative of trans-resveratrol

The present invention relates to the field of compositions comprising ira? -Resveratrol and / or at least one derivative of iraws'-resveratrol in particular as an antioxidant, anti-aging or depigmenting agent.

Resveratrol is a polyphenol of the class of stilbenes that exists cis form and trans form shown below.

transregulated rat ro I cis- resected rat ro I

Iraws-Resveratrol is known to have many biological properties such as anti-oxidant, anti-inflammatory or antitumor activity.

However, iraws'-resveratrol is a photosensitive molecule that irreversibly transforms into its cis isomer under light exposure, whereas the trans isomer is the most active form.

Thus, there remains a need to have a composition containing trans-reservatrol, stable in particular to light.

The inventors have found that it is possible to obtain such a composition, by introducing at least one particular UVA filter and at least one additional UV filter into said composition.

Thus, according to a first of its aspects, the present invention relates to a cosmetic or dermatological composition comprising, in a physiologically acceptable medium, at least iraws'-resveratrol and / or at least one derivative of iraws'-resveratrol, and a filter system comprising a) at least one long UVA filter, liposoluble 2-hydroxybenzophenone substituted amino and b) at least one UV filter selected from water-soluble UVA organic screening agents, liposoluble UVA-UVB mixed organic screening agents, mineral filters and / or mixtures thereof .

Preferably, the compositions according to the invention have an SPF greater than or equal to 25, preferably from 30 to 75 and a PPD greater than or equal to 8, preferably from 10 to 30.

Preferably, iraws'-resveratrol or derivative of iraws'-resveratrol is present in a content ranging from 0.001 to 10% by weight relative to the total weight of the composition. In particular, the composition according to the invention is characterized in that the SPF / PPD ratio ranges from 1 to 5, preferably from 1.5 to 4.5 and better still from 2 to 4.

According to a second aspect, the invention relates to a method for stabilizing, in particular photostabilization, a composition comprising iraws'-resveratrol and / or at least one trans -resveratrol derivative comprising a step in which one adds to said composition a filtering system comprising a) at least one long UVA filter liposoluble 2-hydroxybenzophenone substituted amino and b) at least one UV filter selected from water-soluble UVA organic filters, liposoluble UVA-UVB mixed organic filters, mineral filters and / or their mixtures. Preferably, the SPF of said composition is brought to a value greater than or equal to 25 and the PPD of the composition is brought to a value greater than or equal to 8.

The invention also relates to the use of a filtering system comprising at least one long UVA-soluble liposoluble 2-hydroxybenzophenone amino filter and b) at least one UV-screening agent chosen from water-soluble UVA organic screening agents and liposoluble UVA-UVB mixed organic screening agents. , the mineral filters and / or their mixtures, for stabilizing in particular photostabilize a composition comprising iraws'-resveratrol and / or at least one derivative of trans -resveratrol.

This use comprising in particular the addition to said composition of said filter system in an amount such that the SPF of the composition is brought to a value greater than or equal to 25 and the PPD of the composition is brought to a value greater than or equal to 8.

Surprisingly, the inventors have found that the iraws'-resveratrol present in the composition according to the invention was particularly stable after being exposed to light. By long UVA filter in the sense of the present invention is meant an organic compound filtering absorbing UVA radiation in the wavelength range between 300 and 400 nm and more particularly from 340 to 400 nm.

For the purpose of the present invention, the term "derivative of iraws'-resveratrol" means the esters, glucosides and phosphates of irar-3-verertrol. These compounds all have the same biological properties as trans-resveratrol and are trans-stereochemistry. Like iraws'-resveratrol, they are photosensitive, and irreversibly transform into their cis isomer under light exposure.

By "water-soluble organic UV filter" is meant any organic or inorganic compound filtering UV radiation capable of being completely dissolved in the state molecular or miscible in a liquid aqueous phase or to be solubilized in colloidal form (for example in micellar form) in a liquid aqueous phase.

By "liposoluble organic UV filter" is meant any organic or inorganic compound filtering UV radiation capable of being completely dissolved in the molecular state or miscible in a liquid fatty phase or of being solubilized in colloidal form (for example in the form of micellar) in a liquid fatty phase.

In the following description by "iraws'-resveratrol" is meant trans-resveratrol or at least one derivative of iraws'-resveratrol or a mixture of iraws'-resveratrol and derivative (s) of iraws-resveratrol. By "stable" composition in the sense of the present invention is meant a composition in which the iraws'-resveratrol is degraded little in particular under light exposure, in particular by transformation into its cis isomer. Preferably, a stable composition according to the invention comprises at least 85% by weight of resveratrol, advantageously at least 90% by weight of resveratrol, in particular at least 95% by weight of resveratrol relative to the total weight of resveratrol initially introduced into the composition.

By "SPF" (Sun Protection Factor) within the meaning of the invention is meant the sun protection factor, which measures the level of protection against UVB. The SPF value is the ratio of the minimum duration of sunburn to an antisolar composition to the one without a product. It is expressed mathematically by the ratio of the dose of UV radiation necessary to reach the erythematogenic threshold with the UV filter on the dose of UV radiation necessary to reach the erythematogenic threshold without UV filter. This factor therefore concerns the effectiveness of the protection whose biological action spectrum is centered in the UVB and therefore, accounts for the protection with respect to this UV-B radiation. To characterize the protection against UV-A, the PPD method (Persistent

Pigment Darkening), which measures the skin color observed 2 to 4 hours after exposure of the skin to UV-A, is particularly recommended and used. This method has been adopted since 1996 by the Japanese Cosmetic Industry Association (JCIA) as the official testing procedure for UV-A labeling of products and is frequently used by testing laboratories in Europe and the United States; (Japan Cosmetic Industry Association Technical Bulletin, Measurement Standards for UVA protection efficacy, Issued November 21, 1995 and efective of January 1, 1996).

The UVA PPD sun protection factor (FP UVAppd) is expressed mathematically by the ratio of the UV-A radiation dose required to reach the UV filter pigmentation threshold (MPPDp) on the UV-A radiation dose required for reach the threshold of pigmentation without UV filter (MPPDnp). _{FP U} VA _PPD = ^ ¾

MPPDnp

The present application also relates, in another of its aspects, to the cosmetic use of an effective amount of a composition comprising trans-resveratrol or at least one derivative of iraws'-resveratrol as defined above, for combating cutaneous signs of aging, particularly induced by oxidative stress.

Indeed, the oxidative stress is particularly related to external agents such as ultraviolet radiation, pollution, heat stress or various toxins such as chemicals with which the skin may be in contact (tobacco, heavy metals, air pollutants, etc.). In particular, the use according to the invention aims to attenuate the cutaneous signs of aging, in particular the signs of cutaneous aging of actinic origin such as photo-aging.

Among the cutaneous signs of aging, in particular induced by oxidative stress, in particular of actinic origin, mention is made in particular of a loss of firmness and / or of elasticity and / or of tonicity and / or of flexibility of the skin, the formation wrinkles and fine lines, expression lines, in particular at the level of the forehead and the intersuracillary space, the wrinkles and / or perioral ridicules, and / or the relaxation at the level of the contour of the lips, in particular at the level of level of the white lip (area between the upper lip and the nose), a dullness of the complexion, the papery aspect of the skin. This use will be especially for people with mature skin, or very mature.

By "mature skin" according to the invention is meant in particular persons having at least 40 years.

By "very mature skin" according to the invention is meant in particular persons having at least 50 years, in particular at least 60 years, or even 65 years.

Expression lines are produced under the effect of the stress exerted on the skin by the skin muscles which allow mimicry. Depending on the shape of the face, the frequency of mimicry and possible tics, they can appear from childhood. Some environmental factors such as oxidative stress, sun exposure, and age do not interfere in their genesis but can dig them further and make them permanent. Expression lines are characterized by the presence of furrows around the orifices of the nose (nasolabial folds), the mouth (para-buccal wrinkles and so-called bitterness wrinkles) and the eyes (wrinkles of the paw d 'oie), around which lie the skin muscles, as well as between the eyebrows (wrinkles of the glabella or the lion) and on the forehead. In particular, it will seek to prevent and / or smooth forehead wrinkles and intersurillary space. The papery appearance of the skin is characterized by a change in the visual appearance, as well as the resistance to touch, of the skin. Specifically, the skin visually looks like a cigarette paper giving it an appearance similar to that of a papyrus leaf. In addition, when it is slightly pinched between the thumb and forefinger, the skin forms fine folds, acute and numerous having the appearance of a crumpled paper. Finally, the touch of the skin shows that its superficial parts are like floating on the deep parts, giving the skin, at the very advanced stage of papery appearance, the appearance of a crumpled paper. The papery appearance of the skin is visible on the face and even more characteristic on the back of the hands of the elderly. The compositions according to the invention for preventing and / or smoothing expression lines will be applied to the face.

The compositions according to the invention intended to prevent and / or treat the papery appearance of the skin will be applied in particular on the back of the hands.

The compositions according to the invention intended to reduce the appearance and / or the visibility of the pores will be applied in particular at the level of the zone T (forehead, nose, cheeks, chin).

The use of antioxidant active agents may be useful in anti-aging compositions or in depigmenting compositions.

The use according to the invention may also be more particularly intended for people with oily skin.

The compositions in accordance with the invention may be makeup or care products for keratinous substances, in particular the skin.

More specifically, the makeup products may be of the foundation type, blushers or eyeshadow, anti-ring products, blush, or a product for body makeup or skin coloring.

The skincare products may be a protection, treatment or care composition for the face, for the hands, for the feet, for large anatomical folds or for the body, for example, day creams, night cream, sunscreen composition, body care or care milks, after-sun milks, lotion, gel or mousse for skin care, artificial tanning composition; or an aftershave composition.

The present invention also relates to a cosmetic treatment method for the skin and / or its integuments intended to prevent and / or treat cutaneous aging, in particular induced by oxidative stress, comprising at least one step of applying to a skin and / or or its integuments exhibiting signs of cutaneous aging induced by oxidative stress, at least one effective amount of at least one composition according to the invention. The present invention also relates to a non-therapeutic cosmetic method for limiting the darkening of the skin and / or improving the color and / or the homogeneity of the complexion, comprising the application to the surface of the keratinous material of at least one composition as defined previously. The present invention also relates to a cosmetic treatment method of the skin and / or its integuments, aimed at protecting the skin and / or its integuments from the effects of oxidative stress, in particular the effects of UV radiation, and / or toxins. and / or pollution, comprising at least one step of applying to the skin and / or its integuments at least an effective amount of at least one composition according to the invention. The composition according to the invention is suitable for topical application.

By "skin" is meant the skin of the face and / or the body, the scalp and the semi-mucous membranes (lips). Preferably, it will be the skin of the face and / or body and / or lips.

By "dander" means hair, hair, eyelashes, nails, and preferably hair.

The term "oxidative stress" as used in this application covers all the damage caused in a subject by free radicals.

The extent of the damage caused by this oxidative stress depends on how quickly the free radicals are created and then inactivated by antioxidants. rRANS-RESVERATROL

Resveratrol exists naturally in its cis and trans form, but also in other forms such as a glucosylated form. It is present in many plants and fruits. It is found especially in the Japanese knotweed (Fallopia japonica also known as Polygonum cupistadum or Reynoutria japonica) or in grapes such as those from the vine Vitis vinifera. More particularly, for example, resveratrol is found in blackberries, wine or peanuts.

In general, resveratrol is found in the following families of plants: Vitaceae, Myrtaceae, Dipterocarpaceae, Cyperaceae, Gnetaceae, Fabaceae, Pinaceae, Polygonaceae, Moraceae, Fagaceae, Liliaceae ...

The iraws'-resveratrol present in the composition according to the invention may be of synthetic, natural origin or may be in the form of a plant extract containing iraws-resveratrol.

According to a particular embodiment of the invention, said iraws'-resveratrol and / or at least one derivative of iraws'-resveratrol is present in the composition according to the invention in a content ranging from 0.001 to 10, preferably from 0.01 to 5% by weight, preferably from 0.05 to 2% by weight relative to the total weight of the composition.

For the purposes of the invention, the term "content" means active material.

The present invention also provides a process for preparing said composition.

UVA FILTERS long fat soluble

According to the invention, the composition comprises at least one amino-substituted 2-hydroxybenzophenone liposoluble long UVA filter.

The amino-substituted 2-hydroxybenzophenone compounds according to the invention are preferably chosen from the compounds corresponding to the following formula (I):

in which

1 2

R and R, which are identical or different, denote a C ₁ -C ₂₀ alkyl radical, a C ₂ -C ₂₀ alkenyl, a C ₃ -C ₁₀ cycloalkyl or a C ₃ -C ₁₀ cycloalkenyl radical or form with nitrogen atom with which they are bound a 5- or 6-membered ring; n is a number from 1 to 4; when n = 1, R denotes an alkyl radical C ₁ -C ₂₀ alkenyl radical C ₁ -C ₂₀ hydroxyalkyl C ₁ -C ₅ alkyl, cyclohexyl, C ₆ -C _2, phenyl which may be substituted by O, N or S, an aminocarbonyl radical or a C ₁ -C ₅ alkylcarbonyl radical;

when n = 2, R denotes an alkyl diradical, a cycloalkyl diradical, an alkenyl diradical or an aryl diradical or R with E form a diradical of formula (II):

with m a number ranging from 1 to 3; when n = 3, R is an alkyl triradical; when n = 4, R is an alkyl tetraradical;

E is -O-, or -N (R ⁴ ) - or N; R ⁴ is hydrogen, alkyl C ₁ -C ₅ hydroxyalkyl or C ₁ -C _5.

Examples of C ₁ -C ₂₀ alkyl radicals that may be mentioned include: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-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, 3,3-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, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl or n-eicosyl.

Examples of C ₃ -C ₁₀ cycloalkyl radicals which may be mentioned include: 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 ₃ -C ₁₀ cycloalkenyl radicals having one or more double bonds, mention may be made of: cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, 1,3-cyclohexadienyl, 1,4-cyclohexadienyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, 1, 5-cyclooctadienyl, cyclooctatetraenyl, cyclononenyl or cyclodecenyl.

Examples of a 5- or 6-membered ring formed by the radicals R 1 and R 2 with the nitrogen atom include, in particular, pyrrolidine or piperidine.

A compound of formula (I) with n = 1 very particularly preferred is n-hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate of formula (a):

such as the product sold under the trade name "UVINUL A Plus ®" by BASF.

A compound of formula (I) with n = 2 very particularly preferred is the derivative (2- {4- [2- (4-diethylamino-2-hydroxy-benzoyl) -benzoyl] -piperazine-1-carbonyl} -phenyl) - (4-diethylamino-2-hydroxy-phenyl) -methanone (CAS 919803-06-8) of formula (b):

which is described in the patent application WO 2007071584. This compound is advantageously used in micronized form (average size of 0.02 to 2 μιη) obtainable for example according to the micronization process described in applications GB-A-2 303. 549 and EP-A-893119 and more particularly in the form of an aqueous dispersion.

The compounds of formula (I) as defined above are known per se and their structures and their syntheses are described in patent applications EP-A-1046391, EPI 133980, DE10012408 and WO 2007071584. The filter (s) UVA-long liposoluble 2-hydroxybenzophenone aminosubstituted are preferably present in the compositions according to the invention at contents which preferably vary from 0.1 to 10% by weight, and more preferably from 0.25 to 5% by weight. relative to the total weight of the composition.

Additional UV FILTERS different from UVA-long filters

As stated above, a composition according to the invention further comprises at least one additional UV filter chosen from UVA organic filters. water-soluble, liposoluble UVA-UVB mixed organic screening agents, mineral filters and / or mixtures thereof,

Preferably, the composition according to the invention comprises at least one additional UV filter chosen from water-soluble UVA organic screening agents. Preferably, the composition according to the invention comprises at least one UV filter chosen from the liposoluble UVA-UVB mixed organic screening agents.

Preferably, the composition according to the invention comprises at least one water-soluble UVA organic filter and at least one liposoluble UVA-UVB mixed organic filter and optionally at least one mineral filter. According to the invention, the composition may also comprise, in addition to the filters defined according to b), at least water-soluble organic UVB screening agents, liposoluble UVB organic screening agents, liposoluble UVA screening agents and mixtures thereof.

Preferably, the composition according to the invention comprises at least one water-soluble UVA organic filter and at least one liposoluble organic UVB filter, and optionally at least one mineral filter.

Preferably, the composition according to the invention comprises at least one water-soluble UVA organic filter, at least one liposoluble UVA-UVB mixed organic filter and at least one liposoluble organic UVB filter, and optionally at least one mineral filter.

Preferably, the composition according to the invention comprises at least one water-soluble UVA organic filter, at least one liposoluble UVA-UVB mixed organic filter, at least one liposoluble organic UVB filter and at least one water-soluble organic UVB filter, and optionally at least one filter. mineral.

UVA filters

The UVA filter (s) according to the present invention may be chosen from the following filters.

1) UVA fat-soluble filters

Dibenzoylmethane compounds:

Butyl Methoxydibenzoylmethane sold in particular under the trade name "PARSOL 1789" by DSM Nutritional Products, Inc .;

Isopropyl Dibenzoylmethane;

aminobenzophenones 2- (4-diethylamino-2-hydroxybenzoyl) benzoate of n-hexyl sold in particular under the trade name "UVINUL A +" by BASF;

Anthranilic compounds:

Menthyl anthranilate sold in particular under the trade name "Neo Heliopan MA" by SYMRISE;

4,4-diarylbutadiene compounds:

1,1-dicarboxy (2,2'-dimethyl-propyl) -4,4-diphenylbutadiene;

Merocyanine compounds:

Octyl-5-N, N-diethylamino-2-phenysulfonyl-2,4-pentadienoate; 2) Water-soluble UVA filters

Camphor compounds such as Terephthalylidene Dicamphor Sulfonic Acid manufactured under the name "Mexoryl SX" by Chimex,

The bis-benzoazolyl compounds as described in patents EP 669 323 and US 2,463,264 and more particularly the compound Disodium Phenyl Dibenzimidazo tetra-sulfonate sold under the trade name "NEO HELIOPAN AP" by SYMRISE;

According to a preferred embodiment, said at least one water-soluble UVA filter is chosen from the water-soluble compounds of camphor and their mixtures.

More particularly, said at least one UVA filter is terephthalylidene dicamphor sulfonic acid. Preferably, a composition according to the invention is characterized in that the said at least one water-soluble UVA filter is present in a content ranging from 1 to 20, in particular from 3 to 15% by weight relative to the total weight of the composition. .

UVB filters

The UVB filter (s) according to the present invention may be selected from the following filters.

1) Liposoluble UVB Filters

Para-aminobenzoate

Ethyl PABA;

Ethyl Dihydroxypropyl PABA;

Ethylhexyl Dimethyl PABA (ESCALOL 507 from ISP); Salicylic compounds:

Homosalate sold in particular under the name "Eusolex HMS" by Rona / EM

Industries;

Ethylhexyl salicylate sold in particular under the name "NEO HELIOPAN OS" by SYMRISE;

Dipropylene glycol salicylate sold in particular under the name "DIPSAL" by

SCHER;

- TEA Salicylate and under the name "NEO HELIOPAN TS" by SYMRISE;

cinnamates

Ethylhexyl methoxycinnamate sold in particular under the trade name

"PARSOL MCX" by DSM Nutritional Products, Inc.;

Isopropyl Methoxy cinnamate;

Isoamyl Methoxy cinnamate sold in particular under the trade name "NEO HELIOPAN E 1000" by SYMRISE;

Diisopropyl Methylcinnamate;

Cinnoxate;

Glyceryl Ethylhexanoate Dimethoxycinnamate;

Β, β'-diphenylacrylate compounds:

Octocrylene, sold in particular under the trade name "UVINUL N539" by BASF;

Etocrylene, sold in particular under the trade name Uvinul N35 by

BASF;

Benzylidene camphor compounds:

3-Benzylidene camphor manufactured under the name "MEXORYL SD" by

CHIMEX;

Methylbenzylidene camphor sold in particular under the name "Eusolex 6300" by Merck;

Polyacrylamidomethyl Benzylidene Camphor manufactured under the name "MEXORYL SW" by CHIMEX;

Triazine compounds:

Ethylhexyl triazone sold in particular under the trade name Uvinul T150 by BASF;

Diethylhexylbutamido triazone sold in particular under the trade name "UVASORB HEB" by SIGMA 3V;

2,4,6-tris (dineopentyl 4'-amino benzalmalonate) -s-triazine;

2,4,6-tris (diisobutyl 4'-amino benzalmalonate) -s-triazine; 2,4-bis (dineopentyl 4'-amino benzalmalonate) -6- (n-butyl 4'-aminobenzoate) -s-triazine;

2,4-bis (n-butyl 4'-amino benzoate) -6- (aminopropyltrisiloxane) -s-triazine; the symmetrical triazine filters described in US Pat. No. 6,225,467, WO 2004/085412 (see compounds 6 and 9) or the "Symetrical Triazine Derivatives" document IP.COM Journal, IP.COM INC. WEST HENRIETTA, NY, US (September 20 2004) including 2,4,6-tris- (biphenyl) -1,3,5-triazine (especially 2,4,6-tris (biphenyl-4-yl-1,3,5-triazine) and 2,4,6-tris (terphenyl) -1,3,5-triazine, the latter two filters being described in BEIERSDORF applications WO 06/035000, WO 06/034982, WO 06/034991, WO 06/035007 , WO 2006/034992, WO 2006/034985).

Imidazoline compounds:

Ethylhexyl Dimethoxybenzylidene Dioxoimidazoline Propionate,

Benzalmalonate compounds:

Benzalmalonate-functional polyorganosiloxanes such as Polysilicone-15 sold in particular under the trade name "PARSOL SLX" by DSM Nutritional Products, Inc.;

Di-neopentyl 4'-methoxybenzalmalonate; 2) Water-soluble UVB filters

The following p-aminobenzoic acid (PABA) compounds: - PABA,

- Glyceryl PABA and

PEG-25 PABA sold in particular under the trade name Uvinul P25 by BASF.

Phenylbenzimidzaole Sulfonic Acid sold in particular under the trade name "Eusolex 232" by Merck,

Ferulic acid

salicylic acid,

DE A methoxycinnamate,

benzylidene camphor Sulfonic Acid manufactured under the name "MEXORYL SL" by CHIMEX,

camphor Benzalkonium Methosulfate manufactured under the name "MEXORYL SO" by CHIMEX.

In particular, said at least one water-soluble UVB filter is selected from Phenylbenzimidzaole Sulfonic Acid. Preferably, a composition according to the invention is characterized in that said at least one water-soluble UVB filter is present in a content ranging from 0.5 to 8, in particular from 1 to 5, relative to the total weight of the composition. . According to a preferred embodiment, said at least one UVB filter included in a composition according to the invention is a liposoluble UVB filter.

In particular, said at least one liposoluble UVB filter is selected from salicylic compounds, cinnamates, β, β'-diphenylacrylate compounds, triazine compounds and mixtures thereof.

Preferably, said at least one liposoluble UVB filter is selected from ethylhexyl salicylate, ethylhexyl methoxycinnamate, octocrylene, ethylhexyl triazone and mixtures thereof. More particularly said liposoluble UVB filter is selected from ethylhexyl methoxycinnamate, ethylhexyl triazone, ethylhexyl salicylate and mixtures thereof.

Preferably, a composition according to the invention is characterized in that said at least one liposoluble UVB filter is present in a content ranging from 0.5 to 20, in particular from 1 to 15, and preferably from 1.2 to 10% by weight relative to the total weight of the composition. According to a variant of the invention, said organic filter system used in the invention comprises one or more mixed filter (s) UVA-UVB.

Mixed UVA - UVB filters

Said at least one mixed UVA-UVB filter may be chosen from the following filters. 1) UVA and UVB mixed liposoluble filters

The UVA - UVB mixed liposoluble filters are preferably chosen from benzophenone compounds; phenylbenzotriazole compounds; methylene bis (hydroxyphenyl benzotriazole) compounds as described in US5,237,071, US 5,166,355, GB2303549, DE 197 26 184 and EP893119; bis-resorcinyl triazine compounds as described in application EP0775698; benzoxazole compounds as described in patent applications EP0832642, EP1027883, EP1300137 and DE10162844; symmetrical triazine filters substituted with naphthalenyl groups or polyphenyl groups described in US Pat. No. 6,225,467, WO2004 / 085412 (see compounds 6 and 9) or the document "Symetrical Triazine Derivatives" IP.COM IPCOM000031257 Journal, INC WEST HENRIETTA , NY, US (September 20, 2004) including 2,4,6-tris (di-phenyl) -triazine and 2,4,6-tris (ter-phenyl) -triazine which is included in WO06 patent applications. / 035000, WO06 / 034982, WO06 / 034991, WO06 / 035007, WO2006 / 034992, WO2006 / 034985, these compounds being advantageously used in micronized form (average particle size of 0.02 to 3 μιη) obtainable for example according to the micronization process described in applications GB-A-2 303 549 and EP-A-893119 and in particular in aqueous dispersion; and their mixtures. Benzophenone compounds

Benzophenone-1 sold in particular under the trade name "UVINUL400®" by BASF;

Benzophenone-2 sold in particular under the trade name Uvinul D 50® by BASF;

Benzophenone-3 or Oxybenzone sold in particular under the trade name "Uvinul M 40®" by BASF;

Benzophenone-4, sold by BASF under the name Uvinul MS 40®:

Benzophenone-5;

Benzophenone-6 sold in particular under the trade name "Helisorbl l" by

Norquay;

Benzophenone-8 sold in particular under the trade name "Spectra-Sorb UV-24®" by American Cyanamid;

Benzophenone-9, sold by BASF under the name Uvinul DS 49®:

Benzophenone-10;

Benzophenone-11;

Benzophenone-12.

Phenyl benzotriazole compounds:

- Drometrizole Trisiloxane sold in particular under the name "Silatrizole" by

RHODIA CHEMISTRY or manufactured under the name "Meroxyl XL®" by the company CHIMEX.

Methylene bis-benzotriazolyl tetramethylbutylphenol, sold in solid form in particular under the trade name "MIXXIM BB / 100" by FAIRMOUNT CHEMICAL or in micronized form in aqueous dispersion, especially under the trade name "TINOSORB M" by CIBA SPECIALTY CHEMICALS;

Methylene bis-benzotriazolyl tetramethylbutylphenol, sold in solid form in particular under the trade name "MIXXIM BB / 100®" by FAIRMOUNT CHEMICAL or in the form of an aqueous dispersion of micronized particles having an average particle size ranging from 0.01 to 5 μm and more preferably from 0.01 to 2 μιη and more particularly from 0.020 to 2 μιη with at least one alkylpolyglycoside surfactant of structure CnH2n + 1 O (C6H10O5) xH in which n is an integer of 8 to 16 and x is the average degree of polymerization of the unit (C6H10O5) and varies from 1.4 to 1.6 as described in GB-A-2 303 549 sold especially under the trade name "TINOSORB M®" by BASF or in the form of a aqueous dispersion of micronized particles having an average particle size ranging from 0.02 to 2μιη and more preferably from 0.01 to 1.5 μιη and more particularly from 0.02 to 1 μιη in the presence of at least one monomer. (C8-C20) alkyl-es polyglycerol ter with a glycerol polymerization degree of at least 5 such as the aqueous dispersions described in the application WO2009 / 063392.

Bis-resorcinyl triazine compounds

Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine sold in particular under the trade name "TINOSORB S®" by BASF. Benzoxazole compounds:

2,4-bis- [5-1 (dimethylpropyl) benzoxazol-2-yl- (4-phenyl) imino] -6- (10 (2-ethylhexyl) imino-1,3,5-triazine sold especially under the name of Uvasorb K2A by Sigma 3V.

The liposoluble mixed UVA-UVB filters are preferably chosen from phenylbenzotriazole compounds and benzophenone compounds, in particular benzophenone-3, drometrizole trisiloxane and methylene bis-benzotriazolyl tetramethylbutylphenol, especially in the form of an aqueous dispersion of micronized particles, and even more particularly phenylbenzotriazole compounds such as Drometrizole Trisiloxane

2) Water-soluble mixed UVA and UVB filters

Benzophenone compounds having at least one sulphonic radical as

Benzophenone-4 sold in particular under the trade name UVINUL MS

40 "by BASF,

Benzophenone-5, and

- Benzophenone-9.

Preferably, said at least one mixed UVA-UVB filter according to the invention is a fat-soluble filter. In particular, said mixed UVA-UVB filter is chosen from phenyl benzotriazole compounds and bis-resorcinyl triazine compounds, more preferably it is chosen from trisiloxane drometrizole, and mixtures thereof.

Preferably, a composition according to the invention is characterized in that said at least one liposoluble UVA-UVB mixed filter is present in a content ranging from 0.5 to 20, in particular from 1 to 15, and preferably from 1 to at 10% by weight relative to the total weight of the composition.

According to a particular embodiment, a composition of the invention is characterized in that it comprises a substituted 2-hydroxybenzophenone amino compound, at least one filter selected from terephthalylidene dicamphersulfonic acid, drometrizole trisiloxane, and mixtures thereof.

According to a first preferred variant, the composition according to the invention additionally comprises the aminosubstituted 2-hydroxybenzophenone compound, ethylhexyltriazone (Uvinul T150), Drometzole Trisiloxane (Mexoryl XL), Terephthalylidene Dicamphor Sulfonic Acid (Mexoryl SX), phenylbenzimidazole, ethylhexyl salicylate with or without TiO ₂ treated or untreated on the surface.

According to a second preferred variant, the composition according to the invention additionally comprises the aminosubstituted 2-hydroxybenzophenone compound, ethylhexyl methoxycinnamate, drometrazole trisiloxane (Mexoryl XL), bisulfite Ethylhexyloxyphenol Methoxyphenyl Triazine (Tinosorb S), Terephthalylidene Dicamphor Sulfonic Acid (Mexoryl SX), with or without TiO2 treated or untreated on the surface.

More particularly, the composition according to the invention comprises the following UV filter mixtures by weight relative to the total weight of the composition:

from 0.1 to 3% of ethylhexyltriazone (Uvinul T150), from 0.5 to 6% of

Drometzole Trisiloxane (Mexoryl XL), 5 to 15% of

Terephthalylidene Dicamphor Sulfonic Acid (Mexoryl SX), from 1 to 5% of ethylhexyl salicylate, from 0.5 to 5 of phenylbenzimidazole, and from 2 to 8% of TiO ₂ treated or not surface-treated by weight relative to the total weight composition;

from 4 to 10% of ethylhexyl methoxycinnamate, from 2 to 6% of

Drometzole Trisiloxane (Mexoryl XL), from 0.2 to 3% of Bis- Ethylhexyloxyphenol Methoxyphenyl Triazine (Tinosorb S), from 5 to

15% Terephthalylidene Dicamphor Sulfonic Acid (Mexoryl _SX), and 2 to 8% Ti0 ₂ treated or untreated surface.

Additives

The composition according to the invention may further comprise additives, for example inorganic filters, active agents, fillers, fats, polymers or silicones.

Inorganic filters (or minerals)

The inorganic filters are chosen from coated or uncoated metal oxide pigments, the average size of the primary particles of which is preferably between 5 nm and 100 nm (preferably between 10 nm and 50 nm), such as for example titanium (amorphous or crystallized in rutile and / or anatase form), iron, zinc, zirconium or cerium which are all UV photoprotective agents well known per se.

The pigments can be coated or uncoated. The coated pigments are pigments which have undergone one or more surface treatments of a chemical, electronic, mechanochemical and / or mechanical nature with compounds as described, for example, in Cosmetics & Toiletries, February 1990, Vol. 105, p. 53-64, such as amino acids, beeswax, fatty acids, fatty alcohols, anionic surfactants, lecithins, sodium, potassium, zinc, iron or aluminum salts of fatty acids, metal alkoxides (titanium or aluminum), polyethylene, silicones, proteins (collagen, elastin), alkanolamines, silicon oxides, metal oxides or sodium hexametaphosphate. In a known manner, the silicones are organosilicon polymers or oligomers with a linear or cyclic, branched or crosslinked structure, of variable molecular weight, obtained by polymerization and / or polycondensation of suitably functionalized silanes, and essentially constituted by a repetition of main units in which the silicon atoms are connected to each other by oxygen atoms (siloxane bond), optionally substituted hydrocarbon radicals being directly bonded via a carbon atom to said silicon atoms.

The term "silicones" also includes the silanes necessary for their preparation, in particular alkyl silanes. The silicones used for coating the pigments suitable for the present invention are preferably chosen from the group containing alkyl silanes, polydialkylsiloxanes, and polyalkylhydrogensiloxanes. Even more preferentially, the silicones are chosen from the group containing octyl trimethyl silane, polydimethylsiloxanes and polymethylhydro-genosiloxanes. Of course, the metal oxide pigments before their treatment with silicones, may have been treated with other surfactants, in particular with cerium oxide, alumina, silica, aluminum, silicon compounds, or mixtures thereof.

The coated pigments are more particularly titanium oxides coated with: - silica such as the product "SUNVEIL" from the company IKEDA and the product

"Eusolex T-AVO" from MERCK

- silica and iron oxide such as the product "SUNVEIL F" of the company

Ikeda,

silica and alumina, such as the products "MICROTITANIUM DIOXIDE MT 500 SA" and "MICROTITANIUM DIOXIDE MT 100 SA" from TAYCA, "TIOVEIL" from TIOXIDE, and "Mirasun TiW 60" from Rhodia,

alumina such as the products "TIPAQUE TTO-55 (B)" and "TIPAQUE TTO-55 (A)" from the company ISHIHARA, and "UVT 14/4" from the company KEMIRA,

alumina and aluminum stearate such as the product "MICROTITANIUM DIOXIDE MT 100 TV, MT 100 TX, MT 100 Z, MT-01 from TAYCA, the products

"Solaveil CT-10 W", "Solaveil CT 100" and "Solaveil CT 200" from the company UNIQEMA,

silica, alumina and alginic acid such as the product "MT-100 AQ" from the company Tayca, alumina and aluminum laurate such as the product "MICROTITANIUM DIOXIDE MT 100 S" from TAYCA,

iron oxide and iron stearate such as the product MICROTITANIUM DIOXIDE MT 100 F from TAYCA, zinc oxide and zinc stearate such as the product BR351 from the company

Tayca,

silica and alumina and treated with a silicone such as the products "MICROTITANIUM DIOXIDE MT 600 SAS", "MICROTITANIUM DIOXIDE MT 500 SAS" or "MICROTITANIUM DIOXIDE MT 100 SAS" from the company TAYCA, - silica, alumina, aluminum stearate and treated with a silicone such as the product "STT-30-DS" from the company TITAN KOGYO,

silica and treated with a silicone such as the product "UV-TITAN X 195" from KEMIRA, or the product SMT-100 WRS from TAYCA.

of alumina and treated with a silicone such as the products "TIPAQUE TTO-55 (S)" from ISHIHARA, or "UV TITAN M 262" from KEMIRA, of triethanolamine such as the product "STT-65- S "from the company TITAN KOGYO,

stearic acid, such as the product "TIPAQUE TTO-55 (C)" from the company ISHIHARA, sodium hexametaphosphate such as the product "MICROTITANIUM DIOXIDE MT 150 W" from the company TAYCA.

Other titanium oxide pigments treated with a silicone are preferably TiO ₂ treated with octyl trimethyl silane and whose average elementary particle size is between 25 and 40 nm, such as that sold under the trade name " T 805 "by the company DEGUSSA SILICES, the TiO 2 treated with a polydimethylsiloxane and whose average elementary particle size is 21 nm, such as that sold under the trade name" 70250 Cardre UF Ti02SI3 "by CARDRE, TiO2 anatase / rutile treated with a polydimethylhydrogensiloxane and whose average elementary particle size is 25 nm such as that sold under the trade name "MICRO TITANIUM DIOXIDE USP GRADE HYDROPHOBIC" by the company COLOR TECHNIQUES.

Uncoated titanium oxide pigments are for example sold by the company Tayca under the trade names "MICROTITANIUM DIOXIDE MT 500 B" or "MICROTITANIUM DIOXIDE MT600 B", by the company DEGUSSA under the name "P 25", by the WACKHER company under the name "Titanium oxide transparent PW ", by the company MIYOSHI KASEI under the name" UFTR ", by the company TOMEN under the name" ITS "and by the company TIOXIDE under the name" TIOVEIL AQ ".

The uncoated zinc oxide pigments are, for example, those marketed under the name "Z-cote" by the company Sunsmart;

those marketed under the name "Nanox" by Elementis;

those marketed under the name "Nanogard WCD 2025" by Nanophase Technologies;

The coated zinc oxide pigments are, for example, those sold under the name "Z-COTE HP1" by the company.

SUNSMART (ZnO coated dimethicone);

those marketed under the name "Zinc Oxide CS-5" by the company Toshibi (ZnO coated with polymethylhydrogenosiloxane);

those marketed under the name "Nanogard Zinc Oxide FN" by Nanophase Technologies (as a 40% dispersion in Finsolv TN, C12-C15 alcohol benzoate);

those marketed under the name "DAITOPERSION ZN-30" and "DAITOPERSION Zn-50" by Daito (dispersions in cyclopolymethylsiloxane / polydimethylsiloxane oxyethylenated, containing 30% or 50% of zinc nano-oxides coated with silica and polymethylhydrogeniloxane; );

those marketed under the name "NFD Ultrafine ZnO" by the company Darkin (ZnO coated with perfluoroalkyl phosphate and a copolymer based on perfluoroalkylethyl dispersed in cyclopentasiloxane);

those marketed under the name "SPD-Z1" by Shin-Etsu (ZnO coated with silicone-grafted acrylic polymer, dispersed in cyclodimethylsiloxane);

those marketed under the name "Escalol ZI 00" by ISP (ZnO treated with alumina and dispersed in the ethylhexyl methoxycinnamate / PVP-hexadecene / methicone copolymer mixture);

those marketed under the name "Fuji ZnO-SMS-10" by the company Fuji Pigment (ZnO coated with silica and polymethylsilsesquioxane); those marketed under the name "Nanox Gel TN" by Elementis (ZnO dispersed at 55% in C12-C15 alcohols benzoate with hydroxystearic acid polycondensate).

Uncoated cerium oxide pigments are sold for example under the name "COLLOIDAL CERIUM OXIDE" by the company RHONE POULENC.

Uncoated iron oxide pigments are for example sold by ARNAUD under the names "NANOGARD WCD 2002 (FE 45B)", "NANOGARD IRON FE 45 BL AQ", "NANOGARD FE 45R AQ," NANOGARD WCD 2006 ( FE 45R) ", or by the company MITSUBISHI under the name" TY-220 "The coated iron oxide pigments are for example sold by the company

ARNAUD under the names "NANOGARD WCD 2008 (FE 45B FN)", "NANOGARD WCD 2009 (FE 45B 556)", "NANOGARD FE 45 BL 345", "NANOGARD FE 45 BL", or by the company BASF under the name " TRANSPARENT IRON OXIDE ".

Mention may also be made of mixtures of metal oxides, in particular titanium dioxide and cerium dioxide, including the titanium dioxide / silica-coated cerium-aluminum alloy mixture sold by the company IKEDA under the name "SUNVEIL A". ", as well as the mixture of titanium dioxide and zinc dioxide coated with alumina, silica and silicone such as the product" M 261 "sold by the company KEMIRA or coated with alumina, silica and glycerin such as that the product "M 211" sold by KEMIRA.

Composite particles

The composition according to the invention may also comprise, as inorganic filters, composite particles.

The composite particles usable according to the present invention comprise a matrix and an inorganic UV filter. The matrix comprises one or more organic and / or inorganic materials. The inorganic UV filter is generally chosen from metal oxides.

According to a preferred variant, the matrix consists essentially of organic and / or inorganic material. The inorganic materials that can be used in the matrix according to the present invention are chosen from the group formed by mica, synthetic mica, talc, sericite, boron nitride, glass, calcium carbonate, barium sulphate hydroxyapatite, silica, silicate, magnesium sulfate, magnesium carbonate, magnesium trisilicate, aluminum oxide, aluminum silicate, calcium silicate, calcium phosphate, oxide magnesium, bismuth oxychloride, kaolin, hydrotalcite, mineral clays, synthetic clays and mixtures thereof. The organic materials that can be used to form the matrix are chosen from the group formed by poly (meth) acrylates, polyamides, silicones, polyurethanes, polyethylenes, polypropylenes, polystyrenes, polyhydroxyalkanoates, polycaprolactams, poly (butylene) succinates, polysaccharides, polypeptides, polyvinylalcohols, polyvinyl resins, fluoropolymers, waxes, polyesters, polyethers, and mixtures thereof.

The inorganic UV filters that can be used in the composite particle are chosen from metal oxides.

Preferably, these metal oxides are selected from titanium dioxide TiO ₂ , zinc oxide ZnO, and iron oxide FeO. In a particularly preferred manner, the inorganic UV filter is TiO ₂ .

These metal oxides can be in the form of particles, of average size generally less than 0.2 μιη. Advantageously, the TiO 2 particles used have an average size less than or equal to 0.1 μιη.

These metal oxides can also be in the form of layers, preferably multilayer of average thickness generally less than 0.2 μιη.

Preferably, the content of composite particles of the composition according to the invention ranges from 1 to 70, preferably 1.5 to 45, preferably from 2 to 20% by weight relative to the total weight of the cosmetic composition.

The composite particles that can be used according to the invention are preferably spherical.

They can be hollow, smooth, rough, or porous.

When the composite particles are in spherical form, they are characterized by an average diameter of between 0.1 μm and 30 μm, preferably between 0.2 μm and 20 μm and more preferably between 0.3 μm and 10 μm, advantageously between 0.5 μιη and 10 μπι.

By "spherical" is meant that the particle has a sphericity index, that is to say the ratio between its largest diameter and its smallest diameter, less than 1.2.

Forms of composite particles

According to a first variant, the composite particles contain a matrix comprising an organic and / or inorganic material in which particles of inorganic UV filter are included. Preferably, the composite particles consist of a matrix comprising an organic and / or inorganic material in which particles of inorganic UV filter are included. According to this embodiment, the matrix has inclusions and inorganic UV filter particles are placed in the inclusions of the matrix.

Preferably, the composite particles are spherical and have inclusions in which particles of inorganic UV filter are placed.

By way of composite particles corresponding to this variant, mention may be made of the Sunsil TIN 50 and Sunsil TIN 40 products marketed by SUNJIN CHEMICAL. These spherical composite particles of average size between 2 and 7 μιη are formed of Ti0 ₂ encapsulated in a silica matrix.

According to a second variant, the composite particles contain a matrix made of an organic and / or inorganic material covered with at least one inorganic UV filter layer that can be connected to the matrix by means of a binder.

According to this second variant, the matrix particles are, preferably, of spherical shape.

According to this second variant, the average thickness of the inorganic UV filter layer is generally about ten nanometers. The average thickness of the inorganic UV filter layer is advantageously between 10 ^" and 0.2 μιη, preferably between 10 ^{" 2} and 0.2 μιη.

According to a third variant, the composite particles contain an inorganic UV filter coated with at least one layer of an organic and / or inorganic material. According to this third variant, the particles of inorganic UV filter are characterized by an average elementary size generally between 10 ^" and 0.2 μιη Advantageously, the particles of metal oxides used have an average elementary size of between 10 ^" and 0, 1 μιη.

The matrix may be formed of one or more organic or inorganic materials. It can then be a continuous phase of materials such as an alloy, that is to say a continuous phase in which the materials are no longer dissociable, or a discontinuous phase of materials, for example consisting of an organic or inorganic material covered with a layer of another organic or inorganic material different.

According to a variant, in particular when the composite particles comprise a matrix covered with a UV filter layer, the composite particles may furthermore be covered with an additional coating, in particular chosen from biodegradable or biocompatible materials, lipid materials such as by Examples are surfactants or emulsifiers, polymers, and oxides.

The composite particles used according to the invention have a size of between 0.1 and 30 μιη, preferably between 0.5 and 20 μιη and more preferably between 0.3 and 10 μιη, advantageously between 0.5 and 10 μιη. . Preferably, the UV filter used in the composite particle is Ti0 ₂ or a mixture of Ti0 ₂ and ZnO.

Preferably, the matrix of the spherical composite particle contains a material or a mixture of materials chosen from: - Si0 _2,

polymethyl methacrylate,

copolymers of styrene and a C1-C5 alkyl (meth) acrylate derivative,

polyamides such as nylons.

By way of composite particles corresponding to this variant, mention may be made of the Sunsil TIN 50 and Sunsil TIN 40 products marketed by SUNJIN CHEMICAL. These spherical composite particles of average size between 2 and 7 μιη are formed of TiO2 encapsulated in a silica matrix.

We can also mention the following particles:

Spherical composite particles of average size between 4 and 8 μιη, containing Ti0 ₂ and SiO ₂ with the trade name Eospoly TR marketed by the company

COLOR CREATIONS,

Composite Particles Containing Ti0 ₂ and a Styrene / Alkyl Acrylate Copolymer Matrix Sold under the Name Eospoly UV TR22 HB 50 by the Company Couleurs Couleurs, Composite Particles Containing Ti0 ₂ and ZnO and a Name PMMA Matrix Sun PMMA-T50 commercialized by the company SUNJIN CHEMICAL.

Among the composite particles that can be used according to the invention, mention may also be made of spherical composite particles containing TiO ₂ and SiO ₂ under the tradename STM ACS-0050510, supplied by the company JGC Catalysts and Chemical. Preferably, the inorganic filters are chosen from titanium dioxide, optionally coated with aluminum hydroxide and stearic acid, titanium dioxide optionally coated with stearic acid and alumina, and mixtures thereof.

According to one particular embodiment of the invention, the at least one inorganic filter is present in the composition according to the invention in a content ranging from 0.01% to 20% by weight, preferably from 0.1% to 10% by weight. weight, preferably from 0.5 to 7% by weight, and in particular from 1 to 6% by weight relative to the total weight of the composition. The compositions in accordance with the present invention may furthermore comprise conventional cosmetic adjuvants, chosen in particular from organic solvents, ionic or nonionic, hydrophilic or lipophilic thickeners, softeners, humectants, opacifiers, stabilizers, emollients and silicones. , defoamers, perfumes, preservatives, anionic, cationic, nonionic, zwitterionic or amphoteric surfactants, fillers, polymers, propellants, alkalizing or acidifying agents or any other ingredient normally used in the field cosmetic and / or dermatological.

Among the organic solvents, mention may be made of lower alcohols and polyols. These can be selected from glycols such as propylene glycol, butylene glycol, dipropylene glycol, glycerin, 1,3-propanediol, pentylene glycol or hexylene glycol.

As hydrophilic thickeners, mention may be made of carboxyvinyl polymers such as Carbopols (Carbomers) and Pemulen (acrylate / C10-C30-alkylacrylate copolymer); polyacrylamides, for example crosslinked copolymers sold under the names Sepigel 305 (CTFA name: polyacrylamide / C13-C14 isoparaffin / Laureth 7) or Simulgel 600 (CTFA name: acrylamide / sodium acryloyldimethyltaurate copolymer / isohexadecane / polysorbate 80) by the company Seppic ; polymers and copolymers of 2-acrylamido-2-methylpropanesulphonic acid, optionally cross-linked and / or neutralized, such as Poly (2-acrylamido-2-methylpropanesulphonic acid) marketed by Hoechst under the trademark "Hostacerin AMPS®" ( CTFA name: ammonium polyacryloyldimethyl taurate or SIMULGEL 800 marketed by the company SEPPIC (CTFA name: sodium polyacryolyldimethyl taurate / polysorbate 80 / sorbitan oleate); copolymers of 2-acrylamido-2-methylpropanesulfonic acid and hydroxyethyl acrylate such as SIMULGEL NS and SEPINOV EMT 10 marketed by the company SEPPIC, cellulosic compounds such as hydroxyethylcellulose, polysaccharides and especially gums such as Xanthan gum, and mixtures thereof.

Mention may be made, as lipophilic thickeners, of synthetic polymers such as the poly C10-C30 alkyl acrylates sold under the name "IPA INTELIMER 13-1" and "INTELIMER IPA 13-6" by the company Landec, or modified clays such as hectorite and its derivatives, such as the products marketed under the Bentone name.

Of course, those skilled in the art will take care to choose the optional additional compound (s) mentioned above and / or their amounts in such a way that the advantageous properties intrinsically attached to the compositions in accordance with the invention are not, or substantially, not, altered by the addition or additions envisaged.

The compositions according to the invention can be prepared according to the techniques well known to those skilled in the art. They may be in particular in the form of direct, inverse or multiple emulsion (O / W, W / O, O / W / H or W / O / W). They may optionally be packaged in an aerosol and be in the form of a spray.

Preferably, the compositions according to the invention are in the form of an oil-in-water or water-in-oil emulsion and more particularly oil-in-water emulsions.

The emulsions generally contain at least one emulsifier chosen from amphoteric, anionic, cationic or nonionic emulsifiers, used alone or as a mixture. The emulsifiers are suitably selected according to the emulsion to be obtained (W / O or O / W). The emulsions may also contain other types of stabilizers, for example fillers, gelling or thickening polymers.

As emulsifying surfactants that may be used for the preparation of W / O emulsions, mention may be made, for example, of alkyl esters or ethers of sorbitan, of glycerol or of sugars; silicone surfactants such as dimethicone copolyols such as dimethicone and PEG / polypropylene glycol (PPG) 18/18 dimethicone, sold under the name "X-22-6711D" by Shin Etsu, and alkyl-dimethicone copolyols such as Laurylmethicone copolyol sold under the name Dow Corning 5200 Formulation Aid by the company Dow Corning; cetyl dimethicone copolyol such as the product sold under the name Abil EM 90R by the company Goldschmidt and the mixture of cetyl dimethicone copolyol, polyglycerol isostearate (4 moles) and hexyl laurate sold under the name ABIL WE 09 by the company Goldschmidt. One or more co-emulsifiers may also be added, which advantageously may be chosen from the group comprising alkylated polyol esters or emulsifying silicone elastomers, such as the mixture of dimethicone and cross-linked dimethicone / PEG polymer. -10/15 sold under the name "KSG-210". Polyol alkyl esters that may especially be mentioned include polyethylene glycol esters such as PEG-30 dipolyhydroxystearate, such as the product sold under the name Arlacel PI 35 by the company ICI.

Examples of glycerol and / or sorbitan esters that may be mentioned are polyglycerol isostearate, such as the product sold under the name Isolan GI 34 by the company Goldschmidt; sorbitan isostearate, such as the product sold under the name Arlacel 987 by the company ICI; sorbitan isostearate and glycerol, such as the product sold under the name Arlacel 986 by the company ICI, and mixtures thereof.

For O / W emulsions, mention may be made, for example, as emulsifiers, of nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated fatty acid and sorbitan esters; oxyalkylenated fatty acid esters (oxyethylenated and / or oxypropylenated) such as the mixture PEG-100 Stearate / Glyceryl Stearate marketed for example by the company ICI under the Arlacel 165; oxyalkylenated fatty alcohol ethers (oxyethylenated and / or oxypropylenated); sugar esters such as sucrose stearate; fatty alcohol and sugar ethers, in particular alkylpolyglucosides (APG) such as decylglucoside and laurylglucoside sold, for example, by Henkel under the respective names Plantaren 2000 and Plantaren 1200, cetostearylglucoside optionally mixed with cetostearyl alcohol; , marketed for example under the name Montanov 68 by the company Seppic, under the name Tegocare CG90 by Goldschmidt and under the name Emulgade KE3302 by Henkel, and arachidyl glucoside, for example in the form of a mixture of arachidic and behenic alcohols and arachidylglucoside sold under the name Montanov 202 by the company Seppic. According to one particular embodiment of the invention, the mixture of the alkylpolyglucoside as defined above with the corresponding fatty alcohol may be in the form of a self-emulsifying composition, as described, for example, in WO- A-92/06778. The following examples illustrate the invention without limiting its scope.

In the description and examples, percentages are percentages by weight. The ingredients are mixed in the order and under the conditions readily determined by those skilled in the art.

Examples

Example 1 Compositions in Accordance with the Invention

The compositions are prepared by mixing the following ingredients: Example 1 (% Example 2

INCI name

by weight) (% by weight)

Disodium EDTA 0.05 0.05

Tocopherol 0.5 0.5

Triethanolamine 2.5 1.7

Conservative qs qs

Sodium hyaluronate 0,001 0,001

Dicapryl carbonate 3

Cetyl alcohol 0.7 0.7

Glycyrrhizate 0.001

Tromethamine 1.25 0.33

Resveratrol 0.25 0.25

N-hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate ("Uvinul A Plus®" 2 2

from BASF)

Ethylhexyl methoxycinnamate 7.1

Butyl methoxydibenzoylmethane 3 example 1 (% example 2

INCI name

by weight) (by weight)

Ethylhexyl salicylate (NEO HELIOPAN

SYMRISE OS)

Ethylhexyl triazone (UVINUL T 150 from

1.5

BASF)

Terephtalylidene dicamphor sulfonic acid

12 7.5

(MEXORYL SX)

Phenylbenzimidazole sulfonic acid 2

Drometrizole trisiloxane (MEXORYL XL) 1 6

Bis-ethylhexyloxyphenol methoxyphenyl

1.5

triazine

Titanium dioxide (and) aluminum A

hydroxide (and) stearic acid

Titanium oxide encapsulated in

silica microspheres (SUNSIL TIN 50 of 6

SUNJIN)

Carrragenian 1

Xanthan gum 0,1

Carbomer 0.4 0.4

Ammonium polyacryloyldimethyl taurate 0.2

ACRYLAMIDE / SODIUM

ACRYLOYLDIMETHYLTAURATE 0.2

Copolymer

Dimethicone 2 CS 4

Dimethicone (DOW CORNING TORAY

SH200 C FLUID 5CS from DOW 3

CORNING)

DIMETHICONE (BELSIL DM 350 from

0.5 0.5

WACKER)

Ethanol 7 3

Glycerin 9,15 4

Glycols 4 7.34

Stearic acid 2 2

Potassium cetyl phosphate 1 1

Glyceryl stearate (and) PEG-100 stearate 1.5 1.5

Sodium cocoyl sarcosinate 1

Water Qspl00 Qspl00

The emulsions of Examples 1 and 2 are fine, homogeneous, shiny, smooth and stable over time.

The residual% in iraws'-resveratrol was measured: Compositions conforming to

the invention

1 2

SPF> 50> 50

PPD 20> 20

Report

3.6 2.2

SPF / PPD

% residual

trans- 100 96

resveratrol ⁽¹⁾ ⁽ The residual percentage of resveratrol is measured after an exposure of the composition at 5 J / cm ² of UV, which corresponds to a daily dose.

The two compositions according to the invention have a residual percentage of resveratrol after exposure of the composition to 5 J / cm ² of UV, very high which means that the latter degrades very little in contact with daylight.

Claims

Cosmetic or dermatological composition comprising, in a physiologically acceptable medium, at least iraws-resveratrol and / or at least one derivative of iraws'-resveratrol, and a filtering system comprising a) at least one long-term UVA-soluble filter 2-hydroxybenzophenone amino-substituted and b) at least one additional UV filter chosen from water-soluble UVA organic screening agents, liposoluble UVA-UVB mixed organic screening agents, mineral filters and / or their mixtures.

2. Composition according to Claim 1, characterized in that the amino-substituted 2-hydroxybenzophenone filter is chosen from the compounds corresponding to the following formula (I):

in which

1 2

R and R, identical or different, denote a C ₁ -C ₂₀ alkyl radical, a C ₂ -C ₂₀ alkenyl, a C ₃ -C ₁₀ cycloalkyl or a C ₃ -C ₁₀ cycloalkenyl or form with the nitrogen atom with which they are linked to a 5- or 6-membered ring; n is a number from 1 to 4; when n = 1, R denotes a C ₁ -C ₂₀ alkyl radical, a C ₁ -C ₂₀ alkenyl radical, a C ₁ -C ₅ hydroxyalkyl radical or a C ₆ -C ₁₂ cyclohexyl radical, a phenyl which may be substituted by O, N or S an aminocarbonyl radical or a C1-C5 alkylcarbonyl radical; when n = 2, R denotes an alkyl diradical, a cycloalkyl diradical, an alkenyl diradical or an aryl diradical or R with E form a diradical of formula (II):

with m a number ranging from 1 to 3; when n = 3, R is an alkyl triradical; when n = 4, R is an alkyl tetraradical; E is -O-, or -N (R) - or N;

R ⁴ is hydrogen, a C 1 -C 5 alkyl or C 1 -C 5 hydroxyalkyl radical.

3. Composition according to one of claims 1 or 2, characterized in that the amino-substituted 2-hydroxybenzophenone filter is n-hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate of formula (a):

4. Composition according to one of claims 1 to 3 characterized in that the amino-substituted 2-hydroxybenzophenone filter is present in contents ranging from 0.1 to 10% by weight, and more preferably from 0.25 to 5%. % by weight relative to the total weight of the composition

5. Composition according to one of claims 1 to 4, wherein said iraws'-resveratrol and / or derivative (s) of iraws'-resveratrol is present in a content ranging from 0.001 to 10%, preferably from 0, From 1 to 5% by weight, preferably from 0.05 to 2% by weight relative to the total weight of the composition.

6. Composition according to one of claims 1 to 5 characterized in that said composition having an SPF greater than or equal to 25 and a PPD greater than or equal to 8.

7. Composition according to one of claims 1 to 6, characterized in that the SPF / PPD ratio ranges from 1 to 5, preferably from 1.5 to 4.5 and better from 2 to 4.

8. Composition according to one of claims 1 to 7, characterized in that the one or more additional UV filters are chosen from at least one water-soluble UVA organic filter and at least one liposoluble UVA-UVB mixed organic filter and optionally at least one filter mineral.

9. Composition according to one of claims 1 to 7, characterized in that the or additional UV filters are selected from at least one water-soluble UVA organic filter and at least one liposoluble organic UVB filter, and optionally at least one mineral filter.

10. Composition according to one of claims 1 to 7, characterized in that the one or more additional UV filters are chosen from at least one water-soluble UVA organic filter, at least one liposoluble UVA-UVB mixed organic filter and at least one organic filter. Liposoluble UVB, and optionally at least one mineral filter.

11. Composition according to one of claims 1 to 7, characterized in that the or additional UV filters are selected from at least one water-soluble UVA organic filter, at least one liposoluble UVA-UVB mixed organic filter, at least one organic filter. Liposoluble UVB and at least one water-soluble organic UVB filter, and optionally at least one mineral filter.

12. Composition according to any one of the preceding claims, characterized in that said at least one water-soluble UVA filter is chosen from fat-soluble compounds of dibenzoylmethane, water-soluble compounds of camphor and mixtures thereof.

13. Composition according to any one of the preceding claims, characterized in that said at least one water-soluble UVA filter is chosen from butyl methoxydibenzoylmethane, terephthalylidene dicamphersulfonic acid and mixtures thereof.

14. Composition according to any one of the preceding claims, characterized in that the said at least one water-soluble UVA filter is present in a content ranging from 1 to 20% and in particular from 3 to 15% by weight relative to the total weight of the composition.

15. Composition according to any one of the preceding claims, characterized in that said at least one liposoluble UVB filter is selected from salicylates, cinnamates, β, β'-diphenylacrylate compounds, triazine compounds and mixtures thereof.

16. Composition according to claim 9 to 11 and 15, characterized in that said at least one liposoluble UVB filter is selected from ethylhexyl salicylate, ethylhexyl methoxycinnamate, ethylhexyl triazone and mixtures thereof.

17. Composition according to any one of the preceding claims 9 to 11, 15, 16, characterized in that the said at least one liposoluble UVB filter is present in a content ranging from 0.5 to 20, in particular from 1 to 15%, and preferably from 1.2 to 10% by weight relative to the total weight of the composition.

18. Composition according to any one of the preceding claims, characterized in that the liposoluble UVA-UVB mixed filter is chosen from phenyl benzotriazole and bis-resorcinyl triazines compounds, preferably from drometrizole trisiloxane, and mixtures thereof.

19. Composition according to any one of the preceding claims 1, characterized in that the said at least one liposoluble UVA-UVB mixed filter is present in a content ranging from 0.5 to 20, in particular from 1 to 15, and preferably from 1 to 10% by weight relative to the total weight of the composition.

20. Composition according to any one of the preceding claims, characterized in that said filtering system comprises at least one additional filter selected from terephthalylidene dicamphersulfonic acid, drometrizole trisiloxane and mixtures thereof.

21. Composition according to any one of the preceding claims, characterized in that it is in the form of an oil-in-water or water-in-oil emulsion and more particularly oil-in-water emulsions.

22. A method for stabilizing, in particular photostabilization, a composition comprising iraws'-resveratrol and / or at least one derivative of iraws'-resveratrol comprising a step in which a filtering system comprising: at least one liposoluble long UVA filter and b) at least one additional UV filter chosen from water-soluble UVA organic screening agents, liposoluble UVA-UVB mixed organic screening agents, mineral filters and / or their mixtures, preferably in an amount such that the SPF of the composition is brought to a value greater than or equal to 25 and the PPD of the composition is brought to a value greater than or equal to 8.

23. Method according to one of claims 21 or 22, characterized in that the or additional UV filters are selected from at least one water-soluble UVA organic filter and at least one liposoluble organic UVB filter, and optionally at least one mineral filter.

24. Method according to one of claims 21 to 23, characterized in that the additional UV filters are chosen from at least one water-soluble UVA organic filter, at least one liposoluble UVA-UVB mixed organic filter and at least one organic filter. Liposoluble UVB, and optionally at least one mineral filter.

25. Method according to one of claims 21 to 23, characterized in that the additional UV filter (s) are chosen from at least one water-soluble UVA organic filter, at least one liposoluble UVA-UVB mixed organic filter, at least one organic filter. Liposoluble UVB and at least one water-soluble organic UVB filter, and optionally at least one mineral filter.

26. Method according to any one of claims 21 to 25, characterized in that said at least one water-soluble UVA filter is selected from fat-soluble compounds of dibenzoylmethane, water-soluble compounds of camphor and mixtures thereof.

27. Method according to any one of claims 21 to 26, characterized in that said at least one water-soluble UVA filter is selected from butyl methoxydibenzoylmethane, terephthalylidene dicamphersulfonic acid and mixtures thereof.

28. Method according to any one of claims 21 to 27, characterized in that said at least one water-soluble UVA filter is present in a content ranging from 1 to 20% and in particular from 3 to 15% by weight relative to the weight. total of the composition.

29. Method according to any one of claims 21 to 28, characterized in that said at least one liposoluble UVB filter is selected from salicylic compounds, cinnamates, β, β'-diphenylacrylate compounds, triazine compounds and mixtures thereof .

30. Process according to any one of claims 21 to 29, characterized in that said at least one liposoluble UVB filter is chosen from ethylhexyl salicylate, ethylhexyl methoxycinnamate, ethylhexyl triazone and their mixtures.

31. Method according to any one of the preceding claims 21 to 30 characterized in that said at least one liposoluble UVB filter is present in a content ranging from 0.5 to 20, in particular from 1 to 15% and preferably from 1.2 to 10% by weight relative to the total weight of the composition.

32. Process according to any one of claims 21 to 31, characterized in that the liposoluble UVA-UVB mixed filter is chosen from phenyl benzotriazole compounds and bis-resorcinyl triazine compounds, preferably from drometrizole trisiloxane, bis-ethylhexyloxyphenol methoxyphenyl triazine, and mixtures thereof.

33. Method according to any one of claims 21 to 32, characterized in that said at least one liposoluble UVA-UVB mixed filter is present in a content ranging from 0.5 to 20, in particular from 1 to 15, and preferably from 1 to 10% by weight relative to the total weight of the composition.

34. Use of a filtering system comprising at least one amino-substituted 2-hydroxybenzophenone liposoluble long UVA filter and at least one additional UV filter chosen from water-soluble UVA organic screening agents, mixed organic UVA-screening filters and Liposoluble UVBs, mineral filters and / or their mixtures for stabilizing in particular photostabilize a composition comprising iraws'-resveratrol and / or at least one derivative of iraws'-resveratrol.

35. Use according to one of claims 34, characterized in that the one or more additional UV filters are chosen from at least one water-soluble UVA organic filter and at least one liposoluble organic UVB filter, and optionally at least one mineral filter.

36. Use according to one of claims 34 or 35, characterized in that the one or more additional UV filters are chosen from at least one water-soluble UVA organic filter, at least one liposoluble UVA-UVB mixed organic filter and at least one organic filter. Liposoluble UVB, and optionally at least one mineral filter.

37. Use according to one of claims 34 to 36, characterized in that the one or more additional UV filters are chosen from at least one water-soluble UVA organic filter, at least one liposoluble UVA-UVB mixed organic filter, at least one organic filter. Liposoluble UVB and at least one water-soluble organic UVB filter, and optionally at least one mineral filter.

38. Use according to any one of claims 34 to 37, characterized in that said at least one water-soluble UVA filter is selected from fat-soluble compounds of dibenzoylmethane, water-soluble compounds of camphor and mixtures thereof.

39. Use according to any one of claims 34 to 38, characterized in that said at least one water-soluble UVA filter is chosen from butyl methoxydibenzoylmethane, terephthalylidene dicamphersulfonic acid and mixtures thereof.

40. Use according to any one of claims 34 to 39, characterized in that said at least one water-soluble UVA filter is present in a content ranging from 1 to 20% and in particular from 3 to 15% by weight relative to the weight. total of the composition.

41. Use according to any one of claims 34 to 40, characterized in that said at least one liposoluble UVB filter is selected from salicylic compounds, cinnamates, β, β'-diphenylacrylate compounds, triazine compounds and mixtures thereof .

42. Use according to any one of claims 34 to 41, characterized in that said at least one liposoluble UVB filter is selected from ethylhexyl salicylate, ethylhexyl methoxycinnamate, ethylhexyl triazone and mixtures thereof.

43. Use according to any one of the preceding claims 34 to 42 characterized in that said at least one liposoluble UVB filter is present in a content ranging from 0.5 to 20, in particular from 1 to 15% and preferably from 1.2 to 10% by weight relative to the total weight of the composition.

44. Use according to any one of claims 34 to 43, characterized in that the liposoluble UVA-UVB mixed filter is chosen from phenyl benzotriazole compounds and bis-resorcinyl triazines compounds, preferably from drometrizole trisiloxane, and their mixtures.

45. Use according to any one of claims 34 to 44, characterized in that said at least one liposoluble UVA-UVB mixed filter is present in a content ranging from 0.5 to 20, in particular from 1 to 15, and preferably from 1 to 10% by weight relative to the total weight of the composition.

46. A non-therapeutic cosmetic method for limiting the darkening of the skin and / or improving the color and / or the homogeneity of the complexion including the application on the skin. surface of the keratinous material of at least one composition as defined in one of claims 1 to 20.