FR3046060A1 - EMULSION OF RESVERATROL - Google Patents

Abstract

The present invention relates to a composition, in particular a cosmetic composition, of the emulsion type and comprising: at least 0.5% by weight, preferably at least 1% by weight of resveratrol relative to its total weight, at least one homo- or copolymer of vinylpyrrolidone (PVP), and at least one hydrocarbon oil solubilizing said resveratrol.

Description

The present invention relates to a particularly cosmetic composition containing a dispersed form of resveratrol in a particular organic solvent medium.

Resveratrol is a polyphenol of the stilbene class that exists in cis form and tram form shown below.

trans-resveratrol cis-resveratrol

Resveratrol, and especially trans-resveratrol, is known to have many biological properties such as antioxidant activity and as such is an interesting substance for the prevention and treatment of age-related skin disorders and / or UV exposure.

It would therefore be particularly interesting to be able to maximize its performance, especially by having galenic formulas concentrated in this asset.

However, this compound which is in solid form at room temperature is very slightly soluble in water or solvents compatible with use in compositions dedicated to the care of keratin materials and in particular the skin.

More specifically, this compound is crystalline at room temperature and has a high melting point (of the order of 250 ° C) requiring for its dissolution significant levels of solvents distinct from water that can impact the sensory and the safety of facial and body care products.

To overcome this constraint, resveratrol is generally formulated in the form of a solid dispersion when concentrations greater than 0.25% are considered. Unfortunately in aqueous continuous phase O / W emulsions widely used in facial skincare creams, resveratrol crystals, of a moderately lipophilic nature, have the disadvantage of interacting by affinity with the surfactant systems and piercing the interfaces with the dispersed fatty phases resulting in a physico-chemical destabilization by coalescence of the globules pierced and bridged by the crystals.

There is therefore a need for particularly cosmetic compositions that are able to carry high concentrations of resveratrol while being devoid of the undesirable effects described above.

There is also a need for resveratrol compositions which are stable over time.

For obvious reasons, it would also be particularly interesting that these compositions are likely to improve the effectiveness of resveratrol.

The purpose of the present invention is precisely to propose a new galenic formulation of resveratrol making it possible to meet the aforementioned expectations.

More specifically, the subject of the invention is a composition, in particular a cosmetic composition, of the emulsion type and comprising: at least 0.5% by weight, preferably at least 1% by weight of resveratrol and preferably trans-resveratrol relative to its total weight, at least one homopolymer or co-polymer of vinylpyrrolidone (PVP), and at least one hydrocarbon oil solubilizing said resveratrol.

According to a preferred embodiment, a composition according to the invention contains at least one solubilizing hydrocarbon oil of resveratrol chosen from lauroyl isopropyl sarcosinate, diisopropyl sebacate, liquid lipophilic sunscreens such as, for example, octocrylene and ethylhexylsalicylate, and mixtures thereof.

Thus, a composition according to the invention advantageously contains at least lauroyl isopropyl sarcosinate as a hydrocarbon oil solubilizing resveratrol, especially such as that marketed under the name Eldew SL205.

According to another variant embodiment, a composition according to the invention may contain, as solubilizing hydrocarbon oil, a mixture of lauroyl isopropyl sarcosinate with at least one lipophilic sunscreen, in particular octocrylene and / or ethylhexylsalicylate, and preferably octocrylene.

According to a preferred embodiment, resveratrol is present in the dispersed state in the aqueous phase of said emulsion.

Advantageously, a composition according to the invention contains at least resveratrol in the dispersed state within its aqueous phase and resveratrol in the solute state.

According to another preferred embodiment, the emulsion is a direct emulsion.

According to another preferred embodiment, a composition according to the invention additionally contains at least one anionic surfactant chosen in particular from salts of glutamic acid, salts of phosphoric acid and fatty alcohol esters and alkyl sulphates. and their mixtures.

Advantageously, it contains a mixture of two or even a mixture of three surfactants chosen from the salts of glutamic acid, the salts of phosphoric acid and fatty alcohol esters and the alkyl sulphates.

Unexpectedly, the inventors have indeed found that it is possible to obtain a satisfactory concentration of resveratrol in stable architectural compositions provided that it is formulated therein in association with at least one homo-or co-polymer. vinylpyrrolidone and at least one solubilizing oil of resveratrol.

As is apparent from the examples below, the inventors have found that the combination, with an aqueous dispersion of resveratrol, of at least one hydrocarbon oil solubilizing resveratrol, makes it possible, against all waiting, to significantly increase the bioavailability cutaneous resveratrol. Moreover, the concomitant presence of polyvinylpyrrolidone makes it possible to guarantee an emulsion stability containing such a combination, hydrocarbon oil (s) solubilizing (s) and resveratrol.

Admittedly, resveratrol has already been formulated, in particular in document PCT / IB2013 / 061219 in an emulsion with hydrophobic UV filters such as, for example, ethylhexylsalicylate. However, these emulsions are devoid of polyvinylpyrrolidone.

Similarly, polyvinylpyrrolidone (PVP) is known as a polymer with an affinity for phenols (European Polymer Journal Vol 13. pp. 269 to 272 Pergamon Press 1977, Bulletin of the USSR Academy of Sciences, Division of Chemical Science, August 1977, Volume 26, Issue 8, pp. 1644-1648), and in particular of a specific affinity with resveratrol by a hydrogen bond donor / acceptor mechanism (Wegiel et al, JOURNAL OF PHARMACEUTICAL SCIENCES, VOL. NO.1, JANUARY 2013, 171). Cosmetic formulations associating polyvinylpyrrolidone with a non-crystalline form of resveratrol are also described in documents WO 2010 102245 and EP 1 507 516. However, to the inventors' knowledge, such a compound has never been associated with crystalline resveratrol and to a hydrocarbon oil solubilizing resveratrol to obtain compositions based on resveratrol, according to the present invention.

The subject of the present invention is also a process for the preparation of a composition according to the invention comprising at least the steps consisting in: providing an aqueous dispersion of resveratrol also containing at least one vinylpyrrolidone homo- or co-polymer (PVP) and, where appropriate, at least one anionic surfactant, especially chosen from the salts of glutamic acid, the salts of phosphoric acid and fatty alcohol esters, the alkyl sulphates and their mixtures, and - introducing said dispersion with mechanical stirring in a solvent medium containing at least one hydrocarbon oil solubilizing resveratrol.

Advantageously, the aqueous dispersion of resveratrol is obtained beforehand by adding resveratrol with mechanical stirring to an aqueous medium containing the homopolymer (s) or co-polymer (s) of vinylpyrrolidone (PVP), and advantageously at least an anionic surfactant preferably chosen from salts of glutamic acid, salts of phosphoric acid and fatty alcohol esters, alkyl sulphates and their mixtures.

As is apparent from the examples below, the aqueous dispersion of resveratrol thus obtained is effectively stabilized and compatible with its subsequent formulation in the form of an emulsion.

In a particular embodiment, the solvent medium containing the solubilizing hydrocarbon oil may already consist of an emulsion.

According to another particular mode, the solvent medium may consist of an oily phase.

The subject of the present invention is also a method of treatment, in particular a cosmetic and therefore advantageously non-therapeutic process, of care and / or make-up of a keratinous material and in particular the skin comprising the application to the said keratin material of a composition such that described above or a composition obtained according to the method as described above.

RESVERATROL DEFINITION

As discussed above, resveratrol can be implemented in its cis form and / or its trans form shown below.

frans-resveratrol c / s-resveratrol

Resveratrol exists naturally in its cis and trans form, but also in other forms such as a glucosylated form.

The resveratrol and in particular the trans-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 resveratrol and in particular trans-resveratrol.

Thus, it is present in many plants and fruits. It is found 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 ...

According to a particular embodiment of the invention, said trans-resveratrol and / or at least one trans-resveratrol derivative is present in the composition according to the invention in a content ranging preferably from 0.5% by weight to 10% by weight relative to the total weight of the composition.

SOLUBILIZING OIL FROM RE S VERATROL

As specified above, an emulsion of the invention contains at least one hydrocarbon oil solubilizing resveratrol.

A composition according to the invention advantageously has a content varying from 1 to 17% by weight and preferably from 3 to 14% by weight of hydrocarbon oil (s) solubilizing (s) resveratrol relative to its total weight.

Similarly, a composition according to the invention advantageously has a content ranging from 1 to 10% by weight and preferably from 3 to 8% by weight of amino acid esters as hydrocarbon solubilizing oil of resveratrol compared to its total weight.

Within the meaning of the invention, a hydrocarbon oil is as defined below.

For the purposes of the invention, a solubilizing oil of resveratrol is an oil capable of solubilizing at least 0.5% by weight and preferably 1% by weight of resveratrol relative to its total weight. This solubilization may have necessitated heating conditions but on the other hand it persists by cooling the resveratrol solution to ambient temperature, that is to say from 18 to 25 ° C.

This hydrocarbon oil solubilizing resveratrol is advantageously non-volatile.

For the purposes of the invention, a non-volatile oil is as defined below.

According to a preferred variant, this hydrocarbon oil solubilizing resveratrol is selected from amino acid esters in particular as defined below and liquid lipophilic organic UV filters. 1. Amino acid esters

They are advantageously chosen from the compounds of formula (I): ## STR2 ## in which: n is an integer equal to 0, 1 or 2, - R 'i represents a linear or branched C5 to C21 alkyl or alkenyl radical, - R'2 represents a hydrogen atom or a C1-C3 alkyl group, - R 3 represents a radical selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, a linear or branched C 3 or C 4 alkyl radical, and R '4 represents a linear C 1 -C 10 alkyl radical; or branched, or a linear or branched C2 to C10 alkenyl radical, or a sterol residue; and - their mixtures.

The amino acid esters which are suitable for the invention, as well as their synthesis process, are described in particular in patent applications EP 1 044 676 and EP 0 928 608 of the company Ajinomoto Co.

In the amino acid esters of formula (II), the group R'i (CO) - is preferably an acyl group of an acid chosen preferably from the group formed by capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, linoleic acid, linolenic acid, oleic acid, isostearic acid, 2-ethylhexanoic acid, fatty acids of coconut oil, palm kernel oil fatty acids. These fatty acids may furthermore have a hydroxyl group. Even more preferably, it will be lauric acid.

The part -N (R'2) CH (R'3) (CH2) n (CO) - of the amino acid ester is preferably chosen from the following amino acids: glycine, alanine, valine, leucine, isoleucine, serine , threonine, proline, hydroxyproline, β-alanine, aminobutyric acid, aminoca-proic acid, sarcosine, or N-methyl-β-alanine.

Even more preferably, it will be sarcosine.

The part of the amino acid esters corresponding to the group OR '4 can be obtained from the alcohols selected from the group formed by methanol, ethanol, propanol, isopropanol, butanol, tert-butanol, isobutanol, 3-methyl-1-butanol, 2 1-methyl-1-butanol, fusel oil, pentanol, hexanol, cyclohexanol, octanol, 2-ethylhexanol, decanol, lauryl alcohol, myristic alcohol, cetyl alcohol, cetostearyl alcohol, stearyl alcohol, oleic alcohol, behenyl alcohol, jojoba alcohol, 2-hexadecyl alcohol, 2-octyldodecanol alcohol and isostearyl alcohol.

These amino acid esters can in particular be obtained from natural sources of amino acids. In this case, the amino acids come from hydrolysis of natural plant proteins (oats, wheat, soybean, palm, coconut) and then necessarily lead to mixtures of amino acids which will then be esterified and then N-acylated. The preparation of such amino acids is more particularly described in patent application FR 2 796 550 which is incorporated herein by reference. 2. Liquid Lipophilic Sunscreens

By "liquid organic lipophilic UV filter" is meant any organic chemical molecule capable of absorbing at least the UV radiation in the wavelength range between 280 and 400 nm; said molecule being in liquid form at room temperature (20-25 ° C) and at atmospheric pressure (760 mmHg) and capable of being miscible in an oily phase.

The organic liquid UV filters that are suitable for the invention may be chosen from: liquid lipophilic β, β-diphenylacrylate compounds, liquid lipophilic salicylate compounds, liquid lipophilic cinnamic compounds, and mixtures thereof. 0 compounds β.β-diphenylacrylate

Among the liquid organic lipophilic UVB filters that can be used according to the invention, mention may be made of liquid lipophilic β, β-diphenylacrylate or α-cyano-l-diphenylacrylate alkyl compounds of formula (I) below:

Wherein R 1 to R 3 may have the following meanings: R 1 and R 1, which may be identical or different, represent a hydrogen atom, a straight or branched chain C 1 -C 12 alkoxy radical or a C 1 -C alkyl radical; C4 straight or branched chain, - Ri and R'i being para para position; R2 represents a straight or branched chain C1-C12 alkyl radical; - R.3 represents a hydrogen atom or the CN radical.

Among the straight or branched chain C1-C8 alkoxy radicals, mention may be made, for example, of methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-amyloxy, isoamyloxy and neopentyloxy radicals. -hexyloxy, n-heptyloxy, n-octyloxy and 2-ethylhexyloxy.

Among the straight or branched chain C1-C4 alkyl radicals, there may be mentioned more particularly the methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl radicals. For the C 1 -C 12 alkyl radicals, there may be mentioned by way of example, in addition to those mentioned above, the n-amyl, isoamyl, neopentyl, n-hexyl, n-heptyl and n-octyl radicals, 2 ethylhexyl, decyl and lauryl.

Among the compounds of general formula (I), the following compounds are more particularly preferred: - 2-ethyl hexyl-α-cyano-P, diphenylacrylate or octocrylene, α-cyano-β, β-diphenylacrylate ethyl, for example Etocrylene sold in particular under the trade name "UVINUL N35®" by BASF, - β, β-diphenylacrylate of 2-ethylhexyl, - β, β-di (4'-methoxyphenyl) acrylate ethyl.

Among the compounds of general formula (I), 2-ethyl hexyl-2-cyano-3,3-diphenylacrylate or octocrylene compound, for example that marketed under the name "UVINUL N539®" by BASF, is more particularly preferred. if) Salicylate compounds

Among the liquid lipophilic salicylate compounds that may be used according to the invention, mention may be made of: Homosalate, in particular that sold under the name "Eusolex HMS®" by Rona / EM Industries, Ethylhexyl Salicylate, in particular that sold under the name "NEO". HELIOPAN OS® "by Symrise. bed) Cinnamate compounds

Among the liquid lipophilic cinnamine compounds that can be used according to the invention, mention may be made of: the ethylhexyl methoxycinnamate sold in particular that sold under the trade name Parsol MCX® by DSM Nutritial Products, Isopropyl Methoxycinnamate, and Isomyl Methoxycinnamate, especially that sold under the trade name NEO HELIOPAN E 1000 by Symrise®.

According to a preferred variant, a composition according to the invention contains, as solubilizing oil, resveratrol at least one amino acid ester and more particularly at least isopropyl N-lauroylsarcosinate of formula CH3- (CH2) ioCO-N (CH3) -CH2-COO-CH (CH3) 2.

According to a preferred embodiment, the weight ratio solubilizing hydrocarbon oil / resveratrol present in the composition according to the invention is at least equal to 4 for example ranges from 5 to 15.

In the case of a solubilizing oil represented by a mixture of at least one amino acid ester and a lipophilic UV filter, this ratio may in particular be greater than 10.

HOMO- OR COPOLYMER OF VINYLPYRROLIDONE

The composition according to the invention comprises at least one homopolymer or copolymer of vinylpyrrolidone (PVP) and preferably at least one homovinylpyrrolidone.

This PVP effectively contributes to stabilizing the dispersion of resveratrol in an aqueous medium.

Among the homopolymers, mention may be made of polyvinylpyrrolidones (PVP) of different molecular weights, the weight average molecular weight of said homopolymer being measured by diffraction of light.

More particularly, the polyvinylpyrrolidones (PVP) are chosen from polyvinylpyrrolidones having a weight average molecular weight ranging from 2,000 Daltons to 3,000,000 Daltons, more particularly having a weight average molecular weight ranging from 30,000 Daltons to 2,000,000 Daltons. preferably having a weight average molecular weight of from 40,000 Daltons to 1,500,000 Daltons.

In a preferred embodiment of the invention, said vinylpyrrolidone homo- and co-polymer (s) present in the composition is (are) chosen from polyvinylpyrrolidone having a weight average molecular weight ranging from 40,000 Daltons to 80,000 Daltons, and polyvinylpyrrolidone having a weight average molecular weight of from 900,000 Daltons to 1,500,000 Daltons. By way of examples of polyvinylpyrrolidones concerning the invention may notably be mentioned those available under the trade names PVP K 30L® from ISP and PVP K 90® from ISP (ASHLAND).

In the composition of the invention, any type of vinylpyrrolidone copolymer can be used.

The term "copolymer" as used herein refers to polymers resulting from the polymerization of vinylpyrrolidone with a single type of monomer, as those resulting from the polymerization of vinylpyrrolidone with several kinds of monomers, and for example with two kinds of monomers leading to the production of of terpolymer.

Among the copolymers, mention may be made of polyvinylpyrrolidone / vinyl acetate (P VP / VA), polyvinylpyrrolidone / butene, polyvinylpyrrolidone / decene, polyvinylpyrrolidone / hexadecene, polyvinylpyrrolidone / dimethylaminoethyl methacrylate (PVP / DMAEMA), polyvinylpyrrolidone / dimethylaminopropyl (meth) copolymers acrylamide, polyvinylpyrrolidone / (meth) acrylic acid / lauryl methacrylate, polyvinylpyrrolidone / vinyl acetate / itaconic acid, polyvinylpyrrolidone / vinyl acetate / vinyl propionate and polyvinylpyrrolidone / vinylcaprolactam / dimethylaminopropylacrylamide / acid or acrylic ester.

In a particular embodiment according to the invention, the homo- and copolymers are chosen from polyvinylpyrrolidones (PVP) and vinylpyrrolidone / vinyl acetate copolymers (PVP / VA).

These co-polymers are commercially available, for example under the trademark LUVISKOL® (PVP and PVP / VA) from BASF and under the names PVP-K or PVP / VA from ISP.

The vinylpyrrolidone homopolymer (s) may be present at a content greater than or equal to 0.1% by weight, preferably at a level ranging from 0.3 to 0.5%. by weight, relative to the total weight of the composition.

According to a preferred embodiment, the weight ratio of said homopolymer (s) and co-polymer (s) of vinylpyrrolidone / resveratrol present in the composition according to the invention is at least equal to 0.2, for example varies from 0.3 to 0.8, and preferably about 0.5.

ANIONIC SURFACTANT

As stated above, a composition according to the invention preferably additionally contains at least one anionic surfactant chosen in particular from surfactants of the glutamic acid salt type, of the phosphoric acid ester and fatty alcohol salt type, alkylsulfate type, and mixtures thereof. 1. Anionic surfactant of glutamic acid salt type

According to one embodiment, a composition according to the invention may comprise at least one glutamic acid salt or in particular an acylglutamic salt (INCI name: acyl glutamic acid).

Particularly suitable for the invention are acyl glutamic acids whose acyl group comprises from 10 to 30 carbon atoms, preferably from 12 to 22 carbon atoms, such as, for example, lauroyl glutamic acid, myristoyl glutamic acid, palmitoyl glutamic acid, stearoyl glutamic acid. , behenoyl glutamic acid, glutamic olivoyl, glutamic cocoyl and the salts of these acids, especially alkali metal salts such as Na, Li, K, preferably Na or K, alkaline earth metal salts such as Mg or salts thereof. ammonium of said acids.

Advantageously, a composition according to the invention contains, as anionic surfactant, at least one glutamate, said glutamate having an alkyl chain of Cx to C20, and a solubilizing counter-cation chosen from sodium, potassium and potassium. ammonium.

Such anionic surfactants are those described in EP 2,335,681. By way of illustration of these glutamate salts, the anionic surfactants chosen from cocoyl glutamates of potassium, methyl cocoyl glutamate of potassium, methyl caproyl of glutamate and sodium, cocoyl sodium glutamate, sodium lauroyl glutamate, methyl cocoyl sodium glutamate, sodium methyl lauroyl glutamate, methyl myristoyl glutamate sodium, sodium methyl oleoyl glutamate, sodium palmitoyl methyl glutamate, sodium methyl stearoyl glutamate, and the like. mixtures.

More particularly, the anionic surfactants are chosen from potassium cocoyl glutamates, potassium methyl cocoyl glutamate, sodium cocoyl glutamate, sodium lauroyl glutamate, sodium methyl cocoyl glutamate, sodium lauroyl methyl glutamate, and mixtures thereof.

According to one embodiment of the invention, at least one anionic surfactant is selected from sodium methyl oleoyl glutamates, sodium N-myristoyl-N-methyl glutamate, sodium salt of oil fatty acid methyl glutamate. coconut and laurylmethyl sodium glutamate.

Such compounds are sold under the name Amisoft by the company Ajinomoto and in particular under the references Amisoft CA, Amisoft LA, Amisoft HS 11 PF, Amisoft MK-11, Amisoft LK-11, Amisoft CK-11, or under the name EUMULGIN SG by the company COGNIS.

Mention may also be made of triethanolamine cocoyl glutamate, sold especially under the name Amisoft CT 12 by the company Ajinomoto, and triethanolamine lauroyl glutamate, sold especially under the name ACYLGLUTAMATE LT-12 by the company Ajinomoto.

As the acyl glutamic acid salt, mention may also be made of the product sold under the reference ACYLGLUTAMATE HS 11 by the company AJINOMOTO and that marketed under the reference ACYLGLUTAMATE HS-21 by the company AJINOMOTO.

There may also be mentioned the mixture of acyl glutamate salts, such as Amisoft LS-22 marketed by AJINOMOTO.

Of course, the compositions of the present invention may also comprise mixtures of anionic surfactants of the glutamate type, such as the mixture of anionic surfactants of glutamate and taurate type, a mixture of glutamates, or a mixture of surfactants of glutamate and sarcosinate type.

According to a particular embodiment, a composition according to the invention comprises the combination of mono-sodium salt of n-stearoyl-L-glutamic acid, more particularly that marketed by the company AJINOMOTO under the reference Amisoft HS 11 PF; with a mixture of cetylstearyl alcohol / cetylstearyl glucoside, more particularly that sold by the company SEPPIC under the name MONTANOV 68®.

The acyl glutamic acid (s) and their salts may be present in the composition according to the invention in an active matter content (MA) ranging from 0.01% to 5% by weight, preferably from 0.1% to 2% by weight. % by weight of the total weight of the composition. 2. Anionic surfactant of the type of phosphoric acid ester and fatty alcohol salts

These surfactants are advantageously alkaline salts of phosphoric acid and fatty alcohol esters comprising from 14 to 36 carbon atoms, preferably from 16 to 18 carbon atoms, such as cetyl alcohol or myristic alcohol.

In particular, they may be chosen from: sodium and potassium salts of monocetyl phosphate, for example the compound marketed under the reference Amphisol K by the company DSM; the alkaline salts of dicetylphosphate, and in particular the sodium and potassium salts; the alkaline salts of dimyristyl phosphate, and in particular the sodium and potassium salts; the alkaline salts of cholesterol sulfate, and in particular the sodium salt; alkaline salts of cholesterol phosphate, and in particular the sodium salt; and the alkylsulphonic derivatives of formula (I): wherein R represents the radicals C16H33 and C18H37 taken as a mixture or separately and M is an alkali metal, preferably sodium.

Preferably, this type of surfactant is chosen from alkaline salts of phosphoric acid and fatty alcohol esters comprising from 14 to 36 carbon atoms, preferably from 16 to 18 carbon atoms such as cetyl alcohol, myristic alcohol, and in particular the sodium and potassium salts of monocetyl phosphate. 3. Alkyl sulphate surfactants

This type of surfactant is very particularly chosen from alkyl ether sulfates, mention may be made, for example, of sodium lauryl ether sulphate (C12-14 70-30) (2.2 EO), such as, for example, that marketed under the names Sipon AOS225. or TEXAPON N702 by Henkel, ammonium lauryl ether sulfate (C12-14 70-30) (3 EO) such as for example that marketed under the name Sipon LEA 370 by Henkel, alkyl (C12- C14) ammonium ether (9 EO) sulfate such as for example that marketed under the name RHODAPEX AB / 20 by the company Rhodia Chimie, and the mixture of lauryl and oleyl ether sodium sulfate and magnesium such as for example that marketed under the name EMPICOL BSD 52 by Albright & Wilson.

According to an alternative embodiment, a composition according to the invention comprises at least one anionic surfactant chosen from triethanolamine cocoyl glutamate, triethanolamine lauroyl glutamate and monocetyl phosphate, and mixtures thereof.

PHYSIOLOGICALLY ACCEPTABLE ENVIRONMENT

The compositions used according to the invention contain a physiologically acceptable medium, that is to say compatible with the keratin materials of human beings such as the skin, the scalp, the hair and the nails.

The compositions according to the invention are advantageously in the form of oil-in-water (O / W) emulsions. These compositions are prepared according to the usual methods.

The composition may thus comprise at least one oil that is distinct from a solubilizing resveratrol oil according to the invention.

As other usable oils distinct from the solubilizing oil detailed above, mention may be made, for example, of: hydrocarbon-based oils of vegetable origin, such as liquid triglycerides of fatty acids containing from 4 to 10 carbon atoms, such as triglycerides heptanoic or octanoic acids or, for example, sunflower oil, corn, soya, squash, grape seed, sesame, hazelnut, apricot, macadamia, arara, castor oil, avocado, triglycerides of caprylic / capric acids such as those sold by the company Stearineries Dubois or those sold under the names "Miglyol 810", "812" and "818" by the company Dynamit Nobel, jojoba oil, the shea butter oil; esters and synthetic ethers, in particular of fatty acids, such as the oils of formulas R 1 COOR 2 and R 1 OR 2 in which R 1 represents the residue of a fatty acid comprising from 8 to 29 carbon atoms, and R 2 represents a hydrocarbon-based chain, branched or unbranched, containing from 3 to 30 carbon atoms, such as for example purcellin oil, isononyl isononanoate, isopropyl myristate, 2-ethylhexyl palmitate, octyl stearate -2-dodecyl, octyl-2-dodecyl erucate, isostearyl isostearate; hydroxylated esters such as isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, triisocetyl citrate; heptanoates, octanoates, decanoates of fatty alcohols; polyol esters, such as propylene glycol dioctanoate, neopentyl glycol diheptanoate and diethylene glycol diisononanoate; and pentaerythritol esters such as pentaerythrityl tetraisostearate; linear or branched hydrocarbons of mineral or synthetic origin, such as paraffin oils, volatile or not, and their derivatives, petroleum jelly, polydecenes, hydrogenated polyisobutene such as parleam oil, fatty alcohols having from 8 to 26 carbon atoms, such as cetyl alcohol, stearyl alcohol and their mixture (cetylstearyl alcohol), octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleic alcohol or linoleic alcohol; silicone oils such as volatile or non-volatile polymethylsiloxanes (PDMS) with a linear or cyclic silicone chain, which are liquid or pasty at room temperature, in particular cyclopolydimethylsiloxanes (cyclomethicones) such as cyclohexasiloxane; polydimethylsiloxanes comprising alkyl, alkoxy or phenyl groups, during or at the end of the silicone chain, groups having from 2 to 24 carbon atoms; phenyl silicones such as phenyltrimethicones, phenyldimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl-dimethicones, diphenylmethyldiphenyltrisiloxanes, 2-phenylethyltrimethylsiloxysilicates, and polymethylphenylsiloxanes; and - their mixtures.

The term "hydrocarbon-based oil" in the list of oils mentioned above, any oil predominantly comprising carbon and hydrogen atoms, and optionally ester, ether, fluoro, carboxylic acid and / or alcohol groups.

The proportion of the oily phase of the emulsion may range from 5 to 80% by weight, and preferably from 5 to 50% by weight relative to the total weight of the composition.

The emulsions generally contain at least one emulsifier, annexed to the anionic surfactant (s) defined above, and especially chosen from amphoteric, cationic or nonionic emulsifiers, used alone or as a mixture, and optionally a -émulsionnant. The emulsifiers are suitably selected according to the emulsion to be obtained (W / O or O / W). The emulsifier and the co-emulsifier are generally present in the composition, in a proportion ranging from 0.3 to 30% by weight, and preferably from 0.5 to 20% by weight relative to the total weight of the composition.

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); oxyalkylenated fatty alcohol ethers (oxyethylenated and / or oxypropylenated); sugar esters such as sucrose stearate; and mixtures thereof such as the mixture of glyceryl stearate and PEG-40 stearate.

The composition according to the invention may also comprise solid bodies at room temperature (25 ° C.), for example fatty acids, such as stearic acid, lauric acid, palmitic acid and oleic acid; waxes such as lanolin, beeswax, Camauba or Candelilla wax, paraffin waxes, microcrystalline waxes, ceresin or ozokerite, synthetic waxes such as polyethylene waxes, Fischer waxes -Tropsch.

These fatty substances may be chosen in a varied manner by those skilled in the art in order to prepare a composition having the desired properties, for example of consistency or texture.

In known manner, the composition according to the invention may also contain adjuvants which are customary in the cosmetic or dermatological field, such as gelling agents, film-forming polymers, preservatives, perfumes, fillers, UV filters, bactericides, odor, dyestuffs, plant extracts, cosmetic and dermatological active ingredients, and salts. The amounts of these various adjuvants are those conventionally used in the field under consideration, and for example from 0.01 to 35% of the total weight of the composition.

As regards the process for preparing the compositions according to the invention and detailed below, it requires the introduction of the dispersion with mechanical stirring of an aqueous dispersion of resveratrol containing PVP and advantageously at least one anionic surfactant within an oil-in-water emulsion.

This introduction carried out with mechanical stirring is generally carried out by applying to the emulsion a high shear such as a rotor / stator Moritz emulsifier at 1000 revolutions / min for 30 minutes or equivalent apparatus. This emulsion may optionally be slightly heated during this operation. The invention is illustrated in more detail in the following examples. The contents of the ingredients are expressed in percentage by weight. EXAMPLES EXAMPLE 1

Formula 1 and Comparative Formulas A and B, the compositions of which are shown in the following table, were prepared.

Table I

Process for producing formula 1 according to the invention

Phase A is prepared by heating to 60 ° C and phase B by heating to 80 ° C. Phase Al is added to A just before emulsification. This emulsification is carried out on the rotor / stator by pouring the mixture A + Al on B + B1 for 5 minutes at 3500rpm, the assembly then being homogenized for 10 minutes at 3000 rpm. Phase C is made by sprinkling the cross polymer acrylate on water. This phase is then introduced into the emulsion with stirring to the blade, when the latter has slightly cooled (50 ° C). D is then introduced. Phase E is prepared by dissolving the PVP in water and then incorporating the anionic surfactant therein; then resveratrol under shear to the rotor / stator. Phase E is introduced into the emulsion under shear at the rotor / stator. F is introduced when the temperature has dropped to 40 ° C, then successively G, H and I.

Process for producing the control formula A

It is prepared according to the method of manufacture of formula 1 without the use of E. In addition, 0.25 g / 100 g of resveratrol is dissolved in phase A and stirring is added to the blade of 0.75 g / 100 g of resveratrol in powder form in post-emulsion (phase J).

Process for producing the control formula B

The method of manufacture of the control formula A is reproduced but without the incorporation of Eldew SL-205 and resveratrol into the phase A. On the other hand, it is stirred with a blade stirring of 1 g / 100 g of resveratrol under powder form in post emulsion. EXAMPLE 2

Evaluation: Physicochemical stability and cutaneous bioavailability of the formulas of Example 1 1. Stability

Formulas 1 and Control A of Example 1 were tested for stability according to the following methodology.

Samples of both formulations were stored for 2 months at 4 ° C, room temperature, 40 ° C and 45 ° C. They were then checked on the following criteria: macroscopic appearance, microscopic appearance (optical microscope x10 magnification, normal and polarized lights), pH, viscosity.

Table II reports on the evaluation results thus obtained.

Table II

The control formula A containing no P VP and thus resveratrol in the dispersed and stabilized state exhibits irreversible instability after 2 months of storage at 45 ° C., with oily release at the surface and at the edges testifying to a phenomenon coalescence of the fatty phase of the emulsion.

In contrast, the formula 1 according to the invention stored for 2 months at 45 ° C has a flocculation (due to the high level of gelling agents) which is a reversible phenomenon and does not show oil release. It is therefore more stable than the formula A control. 2. Assessment of Cutaneous Bioavailability

This evaluation is performed by characterizing the cutaneous absorption of resveratrol.

This dermal absorption has been evaluated according to the Guidelines (OECD guideline for the testing of chemicals: guideline 428, skin absorption: in vitro method (13 April 2004) .The studies are carried out on frozen skin resulting from plastic surgery after application of a finished dose of formulation (ie 5 mg / cm2) for 16 hours Quantitative analysis is performed with a validated LC / MS / MS method, cutaneous bioavailability is measured according to the definition given by the SCCS.

A non-parametric statistical analysis of R-estimators type is used.

Table III below shows the results obtained.

Table III

From these results, it is clear the beneficial effect of the presence of a solubilizing oil resveratrol on the cutaneous bioavailability of resveratrol. Thus, the control formula B which is devoid of it shows the most reduced cutaneous biodispobility.

The taking into account of these results with those illustrating the stability presented above, demonstrate that only a composition according to the invention is likely to have both an excellent stability and a probably higher efficiency resveratrol given the increase cutaneous bioavailability.

Claims (18)

1. Composition, in particular cosmetic, of emulsion type and comprising: at least 0.5% by weight, preferably at least 1% by weight of resveratrol relative to its total weight, at least one homo- or co-polymer vinylpyrrolidone (PVP), and - at least one hydrocarbon oil solubilizing said resveratrol. The composition of claim 1 wherein resveratrol is present as trans-resveratrol. 3. Composition according to claim 1 or 2 wherein resveratrol is present in the dispersed state in its aqueous phase. 4. Composition according to any one of the preceding claims in the form of a direct emulsion. 5. Composition according to any one of the preceding claims, comprising at least one resveratrol solubilizing hydrocarbon oil chosen from lauroyl isopropyl sarcosinate, diisopropyl sebacate, liquid lipophilic sunscreens such as, for example, octocrylene and ethylhexylsalicylate. , and their mixtures. 6. Composition according to any one of the preceding claims comprising at least lauroyl isopropyl sarcosinate as hydrocarbon oil solubilizing resveratrol. 7. Composition according to any one of the preceding claims comprising from 1 to 17% by weight and preferably from 3 to 14% by weight of hydrocarbon oil (s) solubilizing (s) resveratrol relative to its total weight . 8. Composition according to any one of the preceding claims comprising from 1 to 10% by weight and preferably from 3 to 8% by weight of amino acid esters as hydrocarbon solubilizing oil of resveratrol, relative to its weight. total. 9. Composition according to any one of the preceding claims wherein the resveratol is present in the dispersed state in its aqueous phase and in the solute state. 10. Composition according to any one of the preceding claims wherein said homopolymer (s) and copolymer (s) of vinylpyrrolidone is (are) chosen from polyvinylpyrrolidone having a weight average molecular weight ranging from 40,000 Daltons to 80,000 Daltons, and polyvinylpyrrolidone having a weight average molecular weight ranging from 900,000 Daltons to 1,500,000 Daltons. 11. Composition according to any one of the preceding claims comprising a content greater than or equal to 0.1% by weight, preferably a content ranging from 0.3 to 0.5% by weight of homo- and copolymer (s) of vinylpyrrolidone in relation to its total weight. 12. Composition according to any one of the preceding claims comprising a mass ratio of said homopolymer (s) and copolymer (s) of vinylpyrrolidone / resveratrol at least equal to 0.2, in particular ranging from 0.3 to 0.8, and preferably about 0.5. 13. Composition according to any one of the preceding claims comprising at least one anionic surfactant, especially chosen from salts of glutamic acid, salts of phosphoric acid and fatty alcohol esters, alkyl sulphates and their mixtures. 14. The composition according to claim 13, wherein said anionic surfactant (s) is (are) chosen from triethanolamine cocoyl glutamate, triethanolamine lauroyl glutamate and monocetyl phosphate. and their mixtures. 15. Process for the preparation of a composition according to any one of the preceding claims, comprising at least the steps consisting in: providing an aqueous dispersion of resveratrol also containing at least one vinylpyrrolidone homopolymer or co-polymer (PVP) ) and where appropriate at least one anionic surfactant, especially chosen from the salts of glutamic acid, the salts of phosphoric acid and fatty alcohol esters, the alkyl sulphates and their mixtures, and introducing said dispersion with mechanical stirring. in a solvent medium containing at least one hydrocarbon oil solubilizing resveratrol. 16. Method according to the preceding claim, wherein the aqueous dispersion of resveratrol is obtained beforehand by adding resveratrol with mechanical stirring to an aqueous medium containing the (s) homopolymer (s) and copolymer (s) of vinylpyrrolidone (PVP). ) and preferably at least one anionic surfactant, especially chosen from salts of glutamic acid, salts of phosphoric acid and fatty alcohol esters, alkyl sulphates and their mixtures. 17. The method of claim 15 or 16 wherein said solvent medium containing at least one hydrocarbon oil solubilizing resveratrol is an emulsion. 18. Process for the cosmetic treatment of skincare and / or make-up of a keratinous material and in particular of the skin comprising the application to said keratinous material of a composition according to any one of Claims 1 to 14 or of a composition obtained according to any one of claims 15 to 17.