FR3134007A1 - Composition for the care of keratinous materials - Google Patents

Abstract

Composition for the care of keratinous materials The present invention relates to a composition in the form of an oil-in-water emulsion for the care of keratinous materials, comprising: (i) at least one nonionic surfactant chosen from sugar ethers of C8-C22 fatty alcohols; (ii) at least one nonionic ester surfactant comprising a combination of at least one monounsaturated ester and at least one polyglyceryl diester; and (iii) at least one ceramide compound. The present invention also relates to a non-therapeutic process for caring for keratinous materials, comprising the application of said composition to the skin Figure for abstract: Figure 1

Description

composition for the care of keratinous materials

The present invention relates to a cosmetic composition. In particular, the present invention relates to a composition for the care of keratinous materials. The present invention also relates to a non-therapeutic process for caring for keratinous materials.

context of art

The skin acts as a natural barrier between the internal and external environments and therefore plays an important role in vital biological functions such as protection against mechanical and chemical injury, microorganisms and ultraviolet damage. However, skin health and appearance can deteriorate due to environmental factors, genetics, makeup, diet and sun exposure. With aging, the outer layer of skin (epidermis) thins, even though the number of cell layers remains unchanged. On the other hand, the number of cells containing pigments (melanocytes) decreases. As a result, the skin appears pale and translucent. Large pigmented spots (age spots, senile spots or lentigos) may appear in areas exposed to the sun. Changes in connective tissue reduce the strength and elasticity of the skin. This phenomenon is known as elastosis. It is more visible in areas exposed to the sun (solar elastosis). Elastose gives skin the leathery, weather-worn appearance found in farmers, sailors, and people who spend a lot of time outdoors. Dehydration increases the risk of skin damage. A poor diet can also negatively impact the skin, causing dryness, breakouts and swelling.

Ceramides are a group of natural waxy and fatty substances found in the skin, composed of sphingosine and lipids (fatty acids) linked together. Ceramides make up about 50% of all lipids in the skin and are made in the lower living cells of the epidermis. As cells mature and move toward the surface, ceramides are released into the top layer, the stratum corneum. In the stratum corneum, ceramides combine with cholesterol (another important lipid found in the skin) and fatty acids to form an orderly, very dense, layered, sheetlike arrangement between dead cells. Ceramides and cholesterol protect the skin against moisture loss, keeping it young and supple, and support the skin's matrix, keeping it firm. Young individuals produce enough ceramides and cholesterol to maintain healthy skin. However, with aging, the production of ceramides and cholesterol decreases, and the skin begins to sag and wrinkle.

In order to achieve stabilization and restorative effectiveness, improving the barrier function of the skin is an essential parameter, which means that transepidermal water loss (TEWL) should be a good attribute to characterize the function of the skin. barrier. However, normal products with superior transepidermal water loss results generally deliver a greasy feeling.

There is therefore a need to formulate a skin care composition which can improve the barrier function of the skin without feeling greasy.

The inventors have now discovered that it is possible to formulate a skin care composition, which can improve skin barrier function without feeling greasy.

Consequently, according to a first aspect, the present invention provides a composition in the form of an oil-in-water emulsion for the care of keratinous materials, comprising:

(i) at least one nonionic surfactant chosen from sugar ethers of C ₈ -C ₂₂ fatty alcohols;

(ii) at least one ester-type nonionic surfactant comprising a combination of at least one monounsaturated ester and at least one polyglyceryl diester; And

(iii) at least one ceramide type compound.

The composition of the present invention is in the form of an oil-in-water emulsion. Thus, said composition comprises a continuous aqueous phase and a dispersed fatty phase.

The inventors have found that the composition of the present invention has a lamellar or liquid crystal structure.

The composition of the present invention can provide good skin barrier function and a non-greasy skin finish.

According to a second aspect, the present invention provides a non-therapeutic method for caring for keratinous materials, comprising the application of the composition according to the first aspect of the present invention to the keratinous materials.

Other advantages of the present invention will appear more clearly on reading the description and examples which follow.

Implementations of the present invention will now be described, by way of example only, with reference to the attached figures, in which:

There shows a photo of the composition of invention example 1 (EI.1) taken with a polarized light microscope.

There shows a photo of the composition of invention example 2 (EI.2) taken with a polarized light microscope.

DETAILED DESCRIPTION OF THE INVENTION

Unless otherwise defined, all technical and scientific terms used in this document have the same meaning as that commonly understood by those skilled in the art to which the present invention belongs. Where the definition of a term in this specification conflicts with the meaning commonly understood by those skilled in the art to which the present invention pertains, the definition described herein applies.

In what follows and unless otherwise indicated, the limits of a range of values are included in this range, in particular in the expressions “between ... and ...” and “ranging from ... to ...” .

Furthermore, the expression “at least one” used in the present description is equivalent to the expression “one or more”.

In this application, the term “comprising” shall be interpreted as including all optional features mentioned, as well as optional, additional and unspecified features. In this document, the use of the term “comprising” also discloses the embodiment in which no features other than those features specifically mentioned are present (i.e. “consisting of”).

Unless otherwise indicated, all numerical values expressing the quantity of ingredients and the like which are used in the description and claims are to be understood as being modified by the term "about". Therefore, unless otherwise stated, the numerical values and parameters described in this document are approximate values which can be modified for the intended purpose, if necessary.

For the purposes of the present invention, the term “keratinous materials” is intended to cover human skin and mucous membranes such as the lips. The skin of the face is more particularly considered according to the present invention.

All percentages in the present invention refer to percentages by weight unless otherwise stated.

According to the first aspect, the present invention provides a composition in the form of an oil-in-water emulsion for the care of keratinous materials, comprising:

(i) at least one nonionic surfactant chosen from sugar ethers of C ₈ -C ₂₂ fatty alcohols;

(ii) at least one ester-type nonionic surfactant comprising a combination of at least one monounsaturated ester and at least one polyglyceryl diester; And

(iii) at least one ceramide type compound.

Nonionic surfactants chosen from sugar ethers of C fatty alcohols ₈ -VS ₂₂

According to the first aspect, the present invention comprises at least one nonionic surfactant chosen from sugar ethers of C ₈ -C ₂₂ fatty alcohols.

Among the sugar ethers, mention may in particular be made of alkylpolyglucosides (APG). An alkylpolyglucoside may be used alone or as a mixture of two or more alkylpolyglucosides. An alkylpolyglucoside generally has a formula (I) of:

R(O)(G) _n (I)

in which :

R is a linear or branched C _8-22 alkyl, preferably a C _8-16 alkyl; G is a residue of a sugar; and n ranges from 1 to 5, preferably from 1.05 to 2.

The sugar for residue G of formula (I) may be selected from the group consisting of glucose, dextrose, fructose, galactose, sucrose, ribose, lactose, maltose, xylose, mannose, cellulose dextran, or starch.

Alkyl polyglucosides useful according to the present invention include, for example,

- decylglucoside, for example the product sold under the name Mydol 10 by the company Kao Chemicals, the product sold under the name Plantaren 2000 by the company Henkel, and the product sold under the name Oramix NS 10 by the company SEPPIC ;

- caprylic/capric glucoside, for example the product sold under the name Oramix CG 110 by the company SEPPIC or under the name Lutensol GD 70 by the company BASF;

- laurylglucoside, for example products sold under the names Plantaren 1200 N and Plantacare 1200 by the company Henkel;

- coco glucoside, for example the product sold under the name Plantacare 818/UP by the company Henkel;

- cetostearyl glucoside optionally mixed with cetostearyl alcohol, sold for example under the name Montanov 68 by the company SEPPIC, under the name Tego-Care CG90 by the company Goldschmidt and under the name Emulgade KE3302 by the company Henkel;

- arachidyl glucoside.

According to one embodiment of the present invention, the APG can be used in mixture with a fatty alcohol, in particular a fatty alcohol having from 8 to 30 carbon atoms, for example from 10 to 20 carbon atoms. Preferably, for such a mixture, the alkylpolyglucoside and the fatty alcohol have similar carbon atoms, for example, with a difference less than 5, in particular less than 3, or less than 2. More preferably, the alkylpolyglucoside and fatty alcohol used in the mixture have the same carbon atoms. For example, the alkyl polyglucoside and the fatty alcohol in the mixture may have the same alkyl moiety.

Alkyl polyglucoside/fatty alcohol mixtures are known in the art, see, for example, WO 9847610 and WO 9513863.

Examples of alkylpolyglucoside/fatty alcohol mixtures may include products sold under the name Montanov series by the company SEPPIC:

- myristyl alcohol/myristyl glucoside: Montanov 14;

- isostearyl alcohol/isostearyl glucoside: Montanov WO 18.

- cetylstearyl alcohol/cetylstearyl glucoside: Montanov 68;

- cetylstearyl alcohol/coconut glucoside: Montanov 82;

- arachidyl alcohol/behenyl alcohol/arachidyl glucoside: Montanov 202;

- C _14-22 alcohol/C _14-22 alkyl glucoside: Montanov L; And

- coconut alcohol/coconut glucoside: Montanov S.

Other useful APGs may include, for example: decyl glucoside and lauryl glucoside, sold, for example, by the Henkel Company under the respective names Plantaren 2000 and Plantaren 1200. In addition, a mixture of cetostearyl glucoside with Cetostearyl alcohol, in addition to Montanov 68, is also sold, for example, under the name Tegocare CG90 by the Goldschmidt company and under the name Emulgade KE3302 by the Henkel company.

Advantageously, the nonionic surfactant chosen from sugar ethers of C ₈ -C ₂₂ fatty alcohols is present in the composition of the present invention in an amount ranging from 0.1% by weight to 10% by weight, preferably from 0.5% by weight to 5% by weight, more preferably from 0.5% by weight to 5% by weight, relative to the total weight of the composition.

Nonionic ester surfactant

According to the first aspect, the composition according to the present invention comprises at least one nonionic ester-type surfactant comprising a combination of at least one monounsaturated ester and at least one polyglyceryl diester.

Preferably, the ester-type nonionic surfactant comprises:

i) at least one monounsaturated ester of formula (II),

R1-C(O)-O-R2 (II)

in which :

R1 and R2 represent, respectively, a C ₁₈ to C ₄₄ fatty chain, at least one of R1 or R2 is monounsaturated; And

ii) at least one polyglyceryl diester of formula (III),

R3-C(O)-(O-CH ₂ -CH(OH)-CH ₂ ) _n -OC(O)-R4 (III)

in which :

R3 and R4 represent, respectively, a C ₁₈ to C ₄₄ fatty chain, saturated linear or branched.

More precisely, in formula (II), R1 and R2 respectively represent a C ₁₈ -C ₄₀ fatty chain, more preferably a C ₁₈ -C ₃₀ fatty chain. At least one of R1 or R2 is monounsaturated.

More particularly, in formula (II), the group R1-C(O)- corresponds to the carbon chain of the fatty acid. This chain can be linear or monounsaturated, and includes at least 18 carbon atoms. We can cite oleic (C18:1), gadoleic (C20:1), erucic (C22:1), up to hexaconenoic acid (C26:1) for unsaturated acids. The R1-C(O)- group can also consist of branched and saturated acids of at least 18 carbon atoms, also called Guerbet acids. The R2-O- group may consist of monounsaturated linear fatty alcohols of at least 18 carbon atoms. We can thus cite octadecenol, eicosenol, docosenol and hexacosenol. The carbon chain of alcohol can also be branched and saturated and have at least 18 carbon atoms. Such alcohols are also called Guerbet alcohols.

Preferably, the monounsaturated ester of formula (II) is a mixture of esters comprising different lengths of fatty chains in their structures. More preferably, such a monounsaturated ester is liquid at room temperature.

As a preferred monounsaturated ester, we can cite, for example, the product commonly called jojoba oil (or jojoba esters), the liquid character being due to the presence of monounsaturated chains. This oil comprises in particular esters of unsaturated fatty acids at C18:1 (preferably minority), C20:1 and C22:1 (preferably majority with C20:1>C22:1), with unsaturated fatty alcohols at C20 :1, C22:1 and C24:1.

Preferably, in formula (III), the group R3-C(O)- corresponds to the carbon chain of a C ₁₈ to C ₄₄ fatty acid, said acid being generally linear and saturated, preferably corresponding to an acid linear and saturated fat in C ₂₀ to C ₃₄ . This therefore includes eicosanoic (or arachidic) acid (C ₂₀ ), docosanoic (or behenic) acid (C ₂₂ ), tetracosanoic (or lignoceric) acid (C ₂₄ ), hexacosanoic (or cerotic) acid (C ₂₆ ). The R4 group corresponds to the hydrocarbon chain of the alcohol, said alcohol being generally linear saturated and having a chain from C ₁₈ to C ₄₄ , preferably from C ₂₀ to C ₃₄ . n is an integer between 2 and 6.

According to the present invention, the polyglyceryl diester is obtained by esterification of a solid wax in the presence of at least one polyol.

The solid waxes suitable for obtaining the polyglyceryl diester have a melting point of between 50 and 90°C. They correspond to mixtures essentially comprising monoesters having the formula R ¹ -C(O)-OR ² , where the group R ¹ -C(O)- corresponds to the carbon chain of the fatty acid, said acid being generally linear and saturated and having a number of carbon atoms of at least 18, and in particular 20, and preferably up to 44 and preferably 34. This therefore includes eicosanoic (or arachidic) acid (C ₂₀ ), docosanoic (or behenic) acid (C ₂₂ ), tetracosanoic (or lignoceric) acid (C ₂₄ ), hexacosanoic (or cerotic) acid (C ₂₆ ). Depending on the origin of the wax, the monoester mixture may also contain a certain proportion of hydroxy acid esters such as hydroxypalmitic or hydroxystearic acid. This is the case, for example, with beeswax. The R ² group corresponds to the hydrocarbon chain of the alcohol, said alcohol being generally linear saturated and having a number of carbon atoms of at least 18, and in particular 20, and preferably up to 44 and preferably 34. Preferably, said alcohol is eicosanol, docosanol or tetracosanol. Examples of waxes include Beeswax, Carnauba Wax, Candelilla Wax, Rice Bran Wax, Sunflower Wax, Ouricury Wax, Shellac Wax, and Sugar Cane Wax. natural solids.

Preferably, the solid wax suitable for the esterification reaction is beeswax.

Preferably, the polyol used for esterification is chosen from the group comprising ethylene glycol, diethylene glycol, triethylene glycol, 2-methyl propanediol, propylene glycol, butylene glycol, neopentyl glycol, hexylene glycol, octylene glycol, polyethylene glycol, polypropylene glycol, trimethylolpropane, sorbitol, erythritol, pentaerythritol, dipentaerythritol, glycerol, diglycerol and polyglycerol (i.e. a polymer of glycerol units). More preferably, the polyol is a polyglycerol, having an average degree of polymerization of between 2 and 6, preferably 3. Preferably, the polyol is polyglycerol-3.

The nonionic ester surfactant also includes the acidic portion of a solid wax. Waxes have a complex composition. They have the common characteristic of containing a mixture of acid monoesters and very long chain fatty alcohols.

Preferably, the nonionic ester surfactant is a wax derivative obtained by reacting together at least one solid wax and at least one monounsaturated ester of formula (II) in the presence of at least one polyol and optionally at least one catalyst. . In this case, a transesterification reaction occurs between the different chemical entities giving the wax derivative.

The preferred catalysts are alkaline or alkaline earth hydroxides or alkoxides, calcium hydroxide, potassium or sodium carbonates or catalysts based on tin or titanium.

Preferably, the solid wax is advantageously chosen from the group comprising carnauba wax, candelilla wax, rice bran wax, sunflower wax, sugar cane wax, ouricury wax, beeswax and shellac wax. .

In a preferred embodiment, the wax derivative is obtained by reacting jojoba oil (also called jojoba wax), beeswax and a polyglycerol, such as polyglycerol-3.

In practice, the reaction is preferably carried out at a temperature between 100°C and 220°C, advantageously between 150°C and 200°C. Preferably, the monounsaturated ester/solid wax mass ratio varies between 5/95 and 95/5, advantageously between 30/70 and 75/25. The mass ratio of esters of formulas (II) and (III)/polyol preferably varies between 1/99 and 99/1, advantageously between 95/5 and 50/50. Preferably, the proportion of esterified polyol represents between 0.5 and 50% by weight of the mixture, the proportion of esterified fatty acids represents between 20 and 60% by weight of the mixture and the proportion of esterified fatty alcohols between 20 and 60 % by weight of the mixture.

Preferably, the nonionic ester surfactant comprises a diester of a C ₁₄ -C ₂₂ fatty acid with a polyglycerol.

Typically, the C ₁₄ -C ₂₂ fatty acid may be selected from the group of myristic, stearic, isostearic, palmitic, oleic, behenic, erucic and arachidic acids, and mixtures thereof.

The polyglycerol may be a polymer of glycerol units, preferably a polymer having an average degree of polymerization of between 4 and 8, preferably 6.

Preferably, said diester is a diester of distearic acid with hexaglycerol. Preferably, it is polyglyceryl-6 distearate.

According to a particular embodiment of the present invention, the nonionic ester type surfactant according to the present invention is present with at least one fatty alcohol comprising from 10 to 30 carbon atoms.

As examples of usable fatty alcohols, we can cite linear or branched fatty alcohols, of synthetic origin or alternatively of natural origin, for example alcohols derived from plant material (coconut, palm kernel, palm, etc. .) or animal (tallow, etc.). A fatty alcohol comprising 20 to 26 carbon atoms is preferably used, preferably 10 to 24 carbon atoms and more preferably 12 to 22 carbon atoms.

As particular examples of fatty alcohols which can be used in the context of the present invention, mention may be made in particular of lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, palmityl alcohol, oleyl alcohol, cetearyl alcohol (mixture of cetyl alcohol and stearyl alcohol), behenyl alcohol, erucyl alcohol and arachidyl alcohol, and mixtures thereof.

Furthermore, it is particularly advantageous, according to the present invention, to use a mixture of polyglyceryl-6 distearate and polyglyceryl-3 beeswax, with cetyl alcohol and jojoba wax. Among the particularly preferred mixtures, mention may be made of the product marketed by the company Gattefosse under the name Emulium ^® Mellifera, comprising jojoba wax, cetyl alcohol, polyglyceryl-6 distearate, and jojoba wax. bee polyglyceryl-3 (INCI name: Polyglyceryl-6 Distearate (and) Jojoba Esters (and) Polyglyceryl-3 Beeswax (and) Cetyl Alcohol). Said mixture comprises 5 to 30% by weight of the total weight of the jojoba wax mixture; from 3 to 15% by weight of cetyl alcohol; at least 50% by weight of polyglyceryl-6 distearate; and 3 to 15% by weight of polyglyceryl-3 beeswax.

Advantageously, the nonionic ester type surfactant is present in the composition of the present invention in an amount ranging from 0.1% by weight to 10% by weight, preferably from 0.5% by weight to 5% by weight, more preferably from 0.5% by weight to 5% by weight, relative to the total weight of the composition.

Ceramide-like compounds

According to the first aspect, the composition of the present invention comprises at least one ceramide type compound.

According to the present invention, the term “ceramide type compound” means natural or synthetic ceramides and/or glycoceramides and/or pseudoceramides and/or neoceramides.

Ceramide-type compounds are disclosed, for example, in patent applications DE 4424530, DE 4424533, DE 4402929, DE 4420736, WO 95/23807, WO 94/07844, EP A 0 646 572, WO 95/16665, FR 2 673 179, EP A 0 227 994, WO 94/07844, WO 94/24097 and WO 94/10131, the teachings of which are included herein by reference.

The ceramide type compounds which can be used according to the present invention preferably correspond to general formula (I):

in which :

- R ₁ represents:

- either a hydrocarbon radical in C ₁ -C ₅₀ , preferably in C ₅ -C ₅₀ , saturated or unsaturated and linear or branched, this radical being able to be substituted by one or more hydroxyl groups optionally esterified with an acid R ₇ COOH, R ₇ being a C ₁ -C ₃₅ hydrocarbon radical optionally mono- or polyhydroxylated, saturated or unsaturated and linear or branched, the hydroxyl(s) of the R ₇ radical being able to be esterified by a C ₁ -C ₃₅ fatty acid, saturated or unsaturated , linear or branched, optionally mono- or polyhydroxylated;

- either a radical R''-(NR-CO)-R', in which R denotes a hydrogen atom or a mono or polyhydroxylated C ₁ -C ₂₀ hydrocarbon radical, preferably monohydroxylated, R' and R'' are hydrocarbon radicals whose sum of carbon atoms is between 9 and 30, R' being a divalent radical;

- either a radical R ₈ -O-CO-(CH ₂ ) _p , in which R ₈ designates a C ₁ -C ₂₀ hydrocarbon radical and p is an integer varying from 1 to 12;

- R ₂ is chosen from a hydrogen atom, a saccharide type radical, in particular a (glycosyl) _n , (galactosyl) _m or sulfogalactosyl radical, a sulfate or phosphate residue, a phosphorylethylamine radical and a phosphorylethylammonium radical, in which n is an integer varying from 1 to 4 and m is an integer varying from 1 to 8;

- R ₃ designates a hydrogen atom or a C ₁ -C ₃₃ hydrocarbon radical, hydroxylated or not, saturated or unsaturated, the hydroxyl(s) being able to be esterified by an inorganic acid or an acid R ₇ COOH, R ₇ having the same meanings as above, and the hydroxyl(s) may be etherified by a (glycosyl) _n , (galactosyl) _m , sulfogalactosyl, phosphorylethylamine or phosphorylethylammonium radical, R ₃ may also be substituted by one or more C ₁ -alkyl radicals. C ₁₄ ;

preferably, R ₃ denotes a C ₁₅ -C ₂₆ α-hydroxyalkyl radical, the hydroxyl group being optionally esterified with a C ₁₆ -C ₃₀ α-hydroxyacid;

- R ₄ designates a hydrogen atom, a methyl or ethyl radical, a C ₃ -C ₅₀ hydrocarbon radical, saturated or unsaturated, linear or branched, optionally hydroxylated or a -CH ₂ -CHOH-CH ₂ -OR ₆ radical , in which R ₆ designates a C ₁₀ -C ₂₆ hydrocarbon radical, or a R ₈ -O-CO-(CH ₂ ) _p radical, in which R ₈ designates a C ₁ -C ₂₀ hydrocarbon radical and p is a integer varying from 1 to 12;

- R ₅ designates a hydrogen atom or a C ₁ -C ₃₀ hydrocarbon radical, saturated or unsaturated, linear or branched, optionally mono or polyhydroxylated, the hydroxyl(s) being able to be etherified by a radical (glycosyl) _n , (galactosyl ) _m , sulfogalactosyl, phosphorylethylamine or phosphorylethylammonium;

provided that when R ₃ and R ₅ represent hydrogen or when R ₃ represents hydrogen and R ₅ represents methyl, then R ₄ does not represent a hydrogen atom or a methyl or ethyl radical.

Among the compounds of formula (I), ceramides and/or glycoceramides of structure described by Downing in Journal of Lipid Research, volume 35, 2060 to 2068, 1994, or those disclosed in French patent application FR 2 673 179 are preferred. , the teachings of which are included here by reference.

The ceramide type compounds more particularly preferred according to the invention are the compounds of formula (I) for which R ₁ denotes an alkyl derived from C ₁₄ -C ₂₂ fatty acids, saturated or unsaturated optionally hydroxylated; R ₂ denotes a hydrogen atom; and R ₃ denotes a linear C ₁₁ -C ₁₇ and preferably C ₁₃ -C ₁₅ radical, optionally hydroxylated. R ₃ preferably denotes an α-hydroxycetyl radical and R ₂ , R ₄ and R ₅ denote a hydrogen atom.

Such compounds are for example:

- 2-N-linoleoylaminooctadecane-1,3-diol,

- 2-N-oleoylaminooctadecane-1,3-diol (N-oleoyldihydrosphingosine),

- 2-N-palmitoylaminooctadecane-1,3-diol,

- 2-N-stearoylaminooctadecane-1,3-diol,

- 2-N-behenoylaminooctadecane-1,3-diol,

- 2-N-[2-hydroxypalmitoyl]aminooctadecane-1,3-diol,

- 2-N-stearoylaminooctadecane-1,3,4-triol and in particular N-stearoylphytosphingosine,

- 2-N-palmitoylaminohexadecane-1,3-diol,

or mixtures of these compounds.

Specific mixtures can also be used, such as, for example, mixtures of ceramide(s) 2 and ceramide(s) 5 according to the Downing classification.

It is also possible to use the compounds of formula (I) for which R ₁ denotes an alkyl radical derived from saturated or unsaturated C ₁₂ -C ₂₂ fatty acids; R ₂ denotes a galactosyl or sulfogalactosyl radical; and R ₃ denotes a saturated or unsaturated C ₁₂ -C ₂₂ hydrocarbon radical and preferably a CH=CH-(CH ₂ ) ₁₂ -CH ₃ group.

We can cite, as an example, the product composed of a mixture of glycoceramides sold under the trade name Glycocer by Waitaki International Biosciences.

It is also possible to use the compounds of formula (I) disclosed in patent applications EP A 0 227 994, EP A 0 647 617, EP A 0 736 522 and WO 94/07844.

These compounds are, for example, Questamide H (bis(N hydroxyethyl-N-cetyl)malonamide), sold by Quest, or N-(2-hydroxyethyl)-N-(3-cetyloxy-2-hydroxy-propyl) cetyl acid amide.

N-docosanoyl-N-methyl-D-glucamine, described in patent application WO 94/24097, can also be used.

Most preferably, the ceramide can be chosen from 2-oleamido-1,3-octadcanediol (its CTFA name), sold for example under the name MEXANYL GZ by Chimex, and ceramide NP (CTFA name N-stearoylphytosphingosine), sold for example under the name CERAMIDE III by EVONIK GOLDSCHMIDT.

Advantageously, the ceramide type compound is present in an amount ranging from 0.01% by weight to 10% by weight, preferably from 0.05% by weight to 5% by weight, more preferably 0.1% by weight. at 2% by weight, relative to the total weight of the composition.

Aqueous phase

As an oil-in-water emulsion, the cosmetic composition of the present invention comprises a continuous aqueous phase.

Said aqueous phase comprises water.

Advantageously, said aqueous phase is present in an amount ranging from 80% by weight to 99% by weight, preferably from 90% by weight to 99% by weight, and more preferably from 95% by weight to 99% by weight relative to to the total weight of the composition.

Oily phase

As an oil-in-water emulsion, the composition of the present invention comprises at least one dispersed oil phase.

Said fatty phase preferably comprises at least one oil.

Oil can be volatile or non-volatile.

The term "oil" refers to a non-aqueous compound immiscible with water that is liquid at room temperature (25°C) and atmospheric pressure (760 mmHg). The term “non-volatile oil” designates an oil which can remain on keratinous materials at room temperature and atmospheric pressure for at least several hours and which in particular has a vapor pressure of less than 10 ^{- 3} mmHg (0.13 Pa). We can also define a non-volatile oil as having an evaporation speed such that, under the conditions defined above, the quantity evaporated after 30 minutes is less than 0.07 mg/cm ² .

These oils can be of vegetable, mineral or synthetic origin.

Said oils can be chosen from hydrocarbon, silicone or fluorinated oils.

By “hydrocarbon-based oil” is meant an oil formed essentially, or even consisting, of carbon and hydrogen atoms, and optionally of O and N atoms, and devoid of Si and N heteroatoms. of F. Such an oil may contain alcohol, ester, ether, carboxylic acid, amine and/or amide groups.

The term “silicone oil” designates an oil containing at least one silicon atom, notably containing Si-O groups.

The term “fluorinated oil” refers to an oil containing at least one fluorine atom.

Advantageously, the oily phase is present in an amount ranging from 0.5% by weight to 15% by weight, preferably from 1% by weight to 10% by weight, more preferably from 1% by weight to 5% by weight, relative to the total weight of the composition of the present invention.

Additional cosmetic active ingredients

The composition of the present invention may include an additional cosmetic active ingredient in addition to the ceramide compound.

As an example of a cosmetic active ingredient, we can cite natural extracts; vitamins such as vitamin A (retinol), vitamin E (tocopherol), vitamin C (ascorbic acid), vitamin B5 (panthenol), vitamin B3 (niacinamide), and derivatives of said vitamins (in particular esters) and mixtures of these; urea; caffeine; salicylic acid and derivatives thereof; alpha-hydroxy acids such as lactic acid or glycolic acid and derivatives thereof; sunscreens; extracts of algae, fungi, plants, yeast and bacteria; enzymes; agents acting on microcirculation, etc.

It is easy for those skilled in the art to adjust the quantity of the additional cosmetic active ingredient depending on the final use of the composition according to the present invention.

Preferably, the composition of the present invention comprises a cosmetic active compound chosen from C-glycosides of formula (V):

(V)

in which :

- R represents a saturated C ₁ to C ₁₀ , in particular C ₁ to C ₄ , alkyl radical which can optionally be substituted by at least one radical chosen from OH, COOH or COOR''_'2 , with R'' ₂ being a saturated C ₁ -C ₄ alkyl radical,

- S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units, in particular up to 6 sugar units, in the form of pyranose and/or furanose and of the L and/or D series, said monosaccharide or polysaccharide being able to be substituted by a necessarily free hydroxyl group and optionally one or more optionally protected amine functional groups, and

_{- _ _ _} (CH ₃ )- and in particular a radical -CO-, -CH(OH)- or -CH(NH ₂ )- and more particularly a radical -CH(OH)-,

the S-CH ₂ -X bond represents a C anomeric bond, which can be α or β, as well as their physiologically acceptable salts, their solvates, such as hydrates, and their optical and geometric isomers.

The C-glycosides of formula (V) useful for the implementation of the invention are in particular those for which R denotes a saturated linear alkyl radical in C ₁ to C ₆ , in particular in C ₁ to C ₄ , preferably in C ₁ to C ₂ , and more preferably a methyl radical.

Mention may in particular be made, among the alkyl groups suitable for implementing the invention, of methyl, ethyl, isopropyl, n-propyl, n-butyl, t-butyl, isobutyl, sec-butyl, pentyl, n -hexyl, cyclopropyl, cyclopentyl or cyclohexyl.

According to one embodiment of the invention, a C-glycoside compound corresponding to formula (V) can be used for which S can represent a monosaccharide or a polysaccharide comprising up to 6 sugar units, in the form of pyranose and/or or furanose and of series L and/or D, said mono- or polysaccharide having at least one necessarily free hydroxyl function and/or optionally one or more necessarily protected amine functions, X and R also retaining all the definitions given above.

Advantageously, a monosaccharide of the invention can be chosen from D-glucose, D-galactose, D-mannose, D-xylose, D-lyxose or L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, acid D-galacturonic, D-iduronic acid, N-acetyl-D-glucosamine or N-acetyl-D-galactosamine and advantageously designates D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose and in particular D -xylose.

More particularly, a polysaccharide of the invention comprising up to 6 sugar units can be chosen from D-maltose, D-lactose, D-cellobiose, D-maltotriose, a disaccharide combining a uronic acid chosen from D-iduronic acid or D-glucuronic acid with a hexosamine chosen from D-galactosamine, D-glucosamine, N-acetyl-D-galactosamine or N-acetyl-D-glucosamine, an oligosaccharide comprising at least one xylose which can advantageously be chosen from xylobiose, methyl- β-xylobioside, xylotriose, xylotetraose, xylopentaose and xylohexaose and in particular xylobiose, which is composed of two xylose molecules joined by a 1-4 bond.

More particularly, S may represent a monosaccharide chosen from D-glucose, D-xylose, L-fucose, D-galactose or D-maltose and in particular D-xylose.

Preferably, a C-glycoside derivative of formula (V) is used for which:

- R represents a C ₁ -C ₄ alkyl radical, in particular a C ₁ -C ₂ , linear unsubstituted alkyl radical, in particular a methyl radical;

- S represents a monosaccharide as described above and chosen in particular from D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, and in particular D-xylose;

- X represents a group chosen from -CO-, -CH(OH)- or -CH(NH ₂ )- and preferably a CH(OH)- group.

Acceptable salts of the compounds described herein include conventional non-toxic salts of said compounds, such as those formed from organic or inorganic acids. We can cite, by way of example, the salts of inorganic acids, such as sulfuric acid, hydrochloric acid. We can also cite salts of organic acids, which may contain one or more carboxylic, sulfonic or phosphonic acid groups. We can cite in particular propionic acid, acetic acid, terephthalic acid, citric acid and tartaric acid.

When the compound of formula (V) comprises an acid group, the neutralization of the acid group(s) can be carried out with an inorganic base, such as LiOH, NaOH, KOH, Ca(OH) ₂ , NH ₄ OH, Mg(OH) ₂ or Zn(OH) ₂ , or with an organic base, such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine. This primary, secondary or tertiary alkylamine may contain one or more nitrogen and/or oxygen atoms and may thus comprise, for example, one or more alcohol functions; we can cite in particular 2-amino-2-methylpropanol, triethanolamine, 2-(dimethylamino)propanol or 2-amino-2-(hydroxymethyl)-1,3-propanediol. Mention may also be made of lysine or 3-(dimethylamino)propylamine.

Acceptable solvates for the compounds described in the present invention include conventional solvates, such as those formed during the final step of preparation of said compounds due to the presence of solvents. We can cite, by way of example, solvates due to the presence of water or linear or branched alcohols, such as ethanol or isopropanol.

Of course, according to the invention, a C-glycoside derivative corresponding to formula (V) can be used alone or in mixture with other C-glycoside derivatives and in any proportion.

A C-glycoside derivative suitable for the invention can in particular be obtained by the synthesis process described in document WO 02/051828.

We can in particular cite, by way of non-limiting illustration of the C-glycoside compounds particularly suitable for the invention, the following compounds:

- C-β-D-xylopyranoside-n-propan-2-one,

- C-α-D-xylopyranoside-n-propan-2-one,

- C-β-D-xylopyranoside-2-hydroxypropane,

- C-α-D-xylopyranoside-2-hydroxypropane,

- 1-(C-β-D-fucopyranoside)propan-2-one,

- 1-(C-α-D-fucopyranoside)propan-2-one,

- 1-(C-β-L-fucopyranoside)propan-2-one,

- 1-(C-α-L-fucopyranoside)propan-2-one,

- 1-(C-β-D-fucopyranoside)-2-hydroxypropane,

- 1-(C-α-D-fucopyranoside)-2-hydroxypropane,

- 1-(C-β-L-fucopyranoside)-2-hydroxypropane,

- 1-(C-α-L-fucopyranoside)-2-hydroxypropane,

- 1-(C-β-D-glucopyranosyl)-2-hydroxypropane,

- 1-(C-α-D-glucopyranosyl)-2-hydroxypropane,

- 1-(C-β-D-galactopyranosyl)-2-hydroxypropane,

- 1-(C-α-D-galactopyranosyl)-2-hydroxypropane,

- 1-(C-β-D-fucofuranosyl)propan-2-one,

- 1-(C-α-D-fucofuranosyl)propan-2-one,

- 1-(C-β-L-fucofuranosyl)propan-2-one,

- 1-(C-α-L-fucofuranosyl)propan-2-one,

- C-β-D-maltopyranoside-n-propan-2-one,

- C-α-D-maltopyranoside-n-propan-2-one,

- C-β-D-maltopyranoside-2-hydroxypropane,

- C-α-D-maltopyranoside-2-hydroxypropane, their isomers and their mixtures.

According to one embodiment, C-β-D-xylopyranoside-2-hydroxypropane or C-α-D-xylopyranoside-2-hydroxypropane and better still C-β-D-xylopyranoside-2-hydroxypropane can advantageously be used for the preparation of a composition according to the invention.

According to a specific embodiment, the C-glycoside compound may be C-β-D-xylopyranoside-2-hydroxypropane (or hydroxypropyl tetrahydropyrantriol) supplied in the form of a solution containing 35% by weight of active material in propylene. glycol.

If it is present, advantageously, the cosmetic active compound chosen from the C-glycosides of formula (V) is present in the composition in an amount ranging from 0.1% by weight to 10% by weight, preferably from 0. 5% by weight to 7% by weight, preferably from 1% by weight to 5% by weight, relative to the total weight of the composition.

Additional adjuvants or additives

The composition of the present invention may also contain conventional cosmetic adjuvants or additives, for example perfumes, chelating agents, preservatives and bactericides, thickeners, pH regulators, fillers and mixtures thereof .

Those skilled in the art can select the quantity of adjuvants or additional additives so as not to have a negative impact on the final use of the composition according to the present invention.

Preferably, the composition of the present invention comprises at least one water-soluble polymer with hydrophobic association.

As used in this document, the term water-soluble polymer with hydrophobic association is understood to mean any amphiphilic polymer having in its structure at least one fatty chain as hydrophobic end and at least one hydrophilic portion as skeleton.

Preferably, the water-soluble polymer with hydrophobic association is chosen from polyethers-polyurethanes with nonionic association, crosslinked polyacrylate polymers and a combination thereof.

- Non-ionic associative polyethers-polyurethanes:

said polymers may contain in their chain both hydrophilic sequences, most often of a polyoxyethylenated nature, and hydrophobic sequences which may be aliphatic bonds alone and/or cycloaliphatic and/or aromatic bonds.

Preferably, these polyether-polyurethanes comprise at least two lipophilic hydrocarbon chains having from 6 to 30 carbon atoms, preferably from 8 to 30, separated by a hydrophilic sequence. It is possible that the hydrocarbon chains are dangling chains or chains at the end of a hydrophilic sequence. In particular, it is possible to consider one or more hanging chains. Additionally, the polymer may comprise a hydrocarbon chain at one end or at both ends of a hydrophilic sequence.

The polyethers-polyurethanes can be polyblocks, in particular in the form of triblocks. The hydrophobic sequences can be at each end of the chain (for example: triblock copolymer with hydrophilic central sequence) or distributed both at the ends and in the chain (polyblock copolymers for example). These same polymers can also be in the form of grafted units or be star-shaped.

The polyether-polyurethane can increase the viscosity or consistency of the composition according to the present invention. Thus, after application of the composition according to the present invention, it can quickly regain the initial elasticity of the composition.

The polyethers-polyurethanes containing a fatty chain can be triblock copolymers whose hydrophilic sequence is a polyoxyethylene chain comprising from 50 to 1,000 oxyethylenated groups.

Polyethers-polyurethanes have a urethane bond between the hydrophilic blocks, hence the origin of the name.

By extension, those whose hydrophilic sequences are linked by other chemical bonds to the hydrophobic sequences are also included among the nonionic polyethers-polyurethanes comprising a hydrophobic chain.

As examples of nonionic polyethers-polyurethanes with a hydrophobic chain which can be used in the present invention, one can also use Rheolate ^® 205 with a urea function sold by the company RHEOX or Rheolates ^® 208, 204 or 212, as well as ^Acrysol® 1840.

We can also cite the product ELFACOS T210 ^® containing a C ₁₂ -C ₁₄ alkyl chain and the product ELFACOS T212 ^® containing a C ₁₈ alkyl chain from the company AKZO.

The product DW 1206B ^® from ROHM & HAAS with C ₂₀ alkyl chain and urethane bond, sold at 20% dry matter in water, can also be used.

It is also possible to use solutions or dispersions of these polymers, particularly in water or in a hydroalcoholic medium. As examples of such polymers, we can cite Rheolate ^® 255, Rheolate ^® 278 and Rheolate ^® 244 sold by the company RHEOX. It is also possible to use the product DW 1206F and DW 1206J supplied by the company ROHM & HAAS.

The polyethers-polyurethanes described above which can be used can also be chosen from those described in the article by G. Fonnum, J. Bakke and Fk. Hansen-Colloid Polym. Sci 271, 380-389 (1993).

As polyethers-polyurethanes described above, mention may be made of polyethers-polyurethanes comprising in their chain at least one polyoxyethylenated hydrophilic block and at least one of the hydrophobic blocks containing at least one sequence chosen from aliphatic sequences, cycloaliphatic sequences and sequences aromatic.

It may be preferable for the polyethers-polyurethanes to comprise at least two lipophilic hydrocarbon-based chains having from 8 to 30 carbon atoms, separated by a hydrophilic block, and in which the hydrocarbon-based chains are chosen from the chains pendants and the chains at the end of the hydrophilic block.

According to a particular form of the present invention, we will use a polyether-polyurethane capable of being obtained by polycondensation of at least three compounds comprising (i) at least one polyethylene glycol comprising from 150 to 180 moles of ethylene oxide, (ii) a polyoxyethylenated stearyl alcohol comprising 100 moles of ethylene oxide, and (iii) a diisocyanate.

Such polyurethanes/polyethers are notably marketed by the company Elementis under the name Rheolate FX 1100 ^® and Rheoluxe 8118, which is a polyethylene glycol polycondensate containing 136 moles of ethylene oxide, polyoxyethylenated stearyl alcohol with 100 moles of ethylene oxide and hexamethylene diisocyanate (HDI) with a weight average molecular mass of 40,000 (INCI name: PEG-136/Steareth-100/HDI Copolymer).

According to another specific form of the present invention, a polyether-polyurethane capable of being obtained by polycondensation of at least three compounds comprising (i) at least one polyethylene glycol comprising from 150 to 180 mol of ethylene oxide will be used. , (ii) stearyl alcohol or decyl alcohol, and (iii) at least one diisocyanate.

These polyurethanes/polyethers are marketed in particular by the company Rohm & Haas under the names Aculyn 46 ^® and Aculyn 44 ^® .

Aculyn 46 ^® with the INCI name: PEG-150/Stearyl Alcohol/SMDI Copolymer, is a polyethylene glycol polycondensate comprising 150 or 180 mol of ethylene oxide, stearyl alcohol and methylenebis (4-cyclohexyl isocyanate) (SMDI) at 15% by weight in a matrix of maltodextrin (4%) and water (81%) (INCI name: PEG-150/Stearyl Alcohol/SMDI Copolymer).

Aculyn 44 ^® (PEG-150/Decyl Alcohol/SMDI Copolymer) is a polyethylene glycol polycondensate comprising 150 or 180 moles of ethylene oxide, decyl alcohol and methylenebis(4-cyclohexyl isocyanate) (SMDI) at 35% by weight in a mixture of propylene glycol (39%) and water (26%) (INCI name PEG-150/Decyl Alcohol/SMDI Copolymer).

As associative polyurethanes, it may be preferable to use a compound represented by the following formula (1):

R ¹ -{(OR ² ) _k -OCONH-R ³ [-NHCOO-(R ⁴ -O) _n -R ⁵ ] _h } _m (1)

in which R ¹ represents a hydrocarbon group, R ² and R ⁴ independently represent alkylene groups having 2 to 4 carbon atoms, which alkylene groups may be the same or different from each other, or a phenylethylene group, R ³ represents a hydrocarbon group, which may optionally have a urethane bond, R ⁵ represents a branched or secondary chain hydrocarbon group, m represents a number of at least 2, h represents a number of at least 1, k represents a number in the range of 1 to 500, and n represents a number in the range of 1 to 200.

The hydrophobically modified polyurethane which is represented by the general formula (1) shown above is obtained, for example, by reacting at least one polyether polyol which is represented by the formula R ¹ -[(OR ² ) _k -OH ] _m , at least one polyisocyanate which is represented by the formula R ³ -(NCO) _h+1 , and at least one polymonoalcohol which is represented by the formula HO-(R ⁴ -O) _n -R ⁵ .

In these cases, R ¹ to R ⁵ in general formula (1) are determined by the compounds R ¹ -[(OR ² ) _k -OH] _m , R ³ -(NCO) _h+1 and HO-(R ⁴ -O) _n -R ⁵ . The charge ratios between the three compounds are not limited in particular and should preferably be such that the ratio of the isocyanate group derived from the polyisocyanate to the hydroxyl group derived from the polyether polyol and the polyether monoalcohol is chosen in the range of NCO/OH between 0.8:1 and 1.4:1.

The polyether polyol compound which is represented by the formula R ¹ -[(OR ² ) _k -OH] _m and which can be preferably used to obtain the associative thickener represented by the general formula (1) can be obtained by polymerization by addition of an m-hydric polyol with an alkylene oxide, such as ethylene oxide, propylene oxide, butylene oxide or epichlorohydrin, or with styrene oxide, and the like.

The polyols are preferably di- to octa-hydric polyols. Examples of di- to octa-hydric polyols include dihydric alcohols, such as ethylene glycol, propylene glycol, butylene glycol, hexamethylene glycol, and neopenthyl glycol; trihydric alcohols, such as glycerol, trioxyisobutane, 1,2,3-butanetriol, 1,2,3-pentanetriol, 2-methyl-1,2,3-propanetriol, 2-methyl-2,3,4-butanetriol, 2-ethyl-1,2,3-butanetriol, 2,3,4-pentanetriol, 2,3,4-hexanetriol, 4-propyl-3,4,5-heptanetriol, 2,4-dimethyl-2,3, 4-pentanetriol, pentamethylglycerol, pentaglycerol, 1,2,4-butanetriol, 1,2,4-pentanetriol, trimethylolethane and trimethylolpropane; tetrahydric alcohols, such as pentaerythritol, 1,2,3,4-pentanetrol, 2,3,4,5-hexanetrol, 1,2,4,5-pentanetrol and 1,3,4,5-hexanetrol; pentahydric alcohols, such as adonitol, arabitol and xylitol; hexahydric alcohols, such as dipentaerythritol, sorbitol, mannitol and iditol; and octahydric alcohols, such as sucrose.

Likewise, R ² is determined by the alkylene oxide, styrene oxide, or the like, which is subjected to the addition. Particularly, for reasons of availability and excellent effects, an alkylene oxide having 2 to 4 carbon atoms, or a styrene oxide is preferable.

The alkylene oxide, styrene oxide, or the like to be subjected to addition may be subjected to single polymerization, or random polymerization, or block polymerization of at least two members. The procedure for addition can be a classic procedure. In addition, the degree of polymerization k can be chosen in the range of 0 to 1000, preferably in the range of 1 to 500, and more preferably in the range of 10 to 200. In addition, the ratio of the ethylene group occupying R ² should preferably be in the range of 50 to 100% by mass relative to the total amount of R ² . In such cases, the appropriate associative thickener for the purposes of the present invention is obtained.

Furthermore, the molecular mass of the polyether polyol compound which is represented by the formula R ¹ -[(OR ² ) _k -OH] _m should preferably be chosen in the range of 500 to 100,000, and should more preferably be chosen in the range of 500 to 100,000. the range from 1,000 to 50,000.

The polyisocyanate which is represented by the formula R ³ -(NCO) _h+1 and which can be preferably used to obtain the hydrophobically modified polyether urethane represented by the general formula (1) used according to the present invention is not limited particularly as the polyisocyanate has at least two isocyanate groups in the molecule. Examples of polyisocyanates include aliphatic diisocyanates, aromatic diisocyanates, alicyclic diisocyanates, biphenyl diisocyanate, phenylmethane diisocyanate, phenylmethane triisocyanate, and phenylmethane tetraisocyanate.

It is also possible to use dimers and trimers (isocyanurate bonds) of the polyisocyanates listed above. In addition, it is possible to use biuret obtained by reaction with an amine.

Furthermore, it is possible to use a polyisocyanate having a urethane bond obtained by a reaction of the above-mentioned polyisocyanate compound and a polyol. As the polyol, di- to octa-hydric polyols are preferable, and the polyols listed above are preferable. In cases where a tri- or more -hydric polyisocyanate is used as the polyisocyanate which is represented by the formula R ³ -(NCO) _n+1 , it is preferable to use the aforementioned polyisocyanate having the urethane bond.

The polyether monoalcohol which is represented by the formula HO-(R ⁴ -O) _n -R ⁵ and which can be preferably used to obtain the hydrophobically modified polyether urethane represented by the general formula (1) used according to the present invention n is not limited in particular to the extent that the polyether monoalcohol is a polyether of a straight chain, branched chain or secondary monohydric alcohol. The polyether monoalcohol may be obtained by addition polymerization of the straight chain, branched chain or secondary monohydric alcohol with an alkylene oxide, such as ethylene oxide, propylene oxide, butylene oxide or epichlorohydrin, or with styrene oxide, and the like.

As a compound represented by general formula (1), polyethylene glycol-240/decyltetraceth-20/hexamethylene diisocyanate copolymer is preferable. Polyethylene glycol-240/decyltetraceth-20/hexamethylene diisocyanate copolymer is also called PEG-240/HDI ether bis-decyltetraceth-20 copolymer.

According to the present invention, it is preferable that the polyether-polyurethane is chosen from the copolymer of steareth-100/PEG-136/HDI sold by the company Rheox under the name Rheolate FX 1100, the copolymer of PEG-240/HDI ether of bis-decyltetradeceth-20 sold by the company Asahi Denka under the name Adekanol GT-700, and a combination thereof.

- Cross-linked polyacrylate polymers

The term “crosslinked polyacrylate polymer”, as used in the present application, designates a copolymer of acrylic acid, methacrylic acid or one of its esters, crosslinked with glycol dimethacrylate.

There follows a non-limiting list of crosslinked polyacrylate polymers, which can be used in the composition of the present invention.

The cross-linked polyacrylate-1 polymer is a copolymer of one or more simple esters of acrylic or methacrylic acid, C _1-4 alkyl methacrylate, C _1-6 dialkylamino, PEG/PPG-30/5 allyl ether , C _10-30 alkyl ether methacrylate of PEG 20-25, C _2-6 hydroxyalkyl methacrylate crosslinked with ethylene glycol dimethacrylate. This copolymer is commercially available under the brand name Carbopol Aqua CC Polymer from Lubrizol Advanced Materials, Inc. (Cleveland, Ohio).

The cross-linked polyacrylate-2 polymer is a copolymer of PEG/PPG-23/6 dimethicone citraconate, PEG-25 C _10-30 alkyl methacrylate and one or more acrylic acid monomers, methacrylic acid or one of their simple esters, crosslinked with trimethylolpropane PEG-15 triacrylate. This copolymer is commercially available under the brand name Fixate Superhold Polymer from Lubrizol Advanced Materials, Inc. (Cleveland, Ohio).

Polyacrylate-3 cross-linked polymer is a copolymer of butyl acrylate, PEG-10 acrylate, PPG-6 acrylate and dimethylacrylamide, cross-linked with PEG-23 diacrylate. This copolymer is commercially available under the trade name Plascize L-64S from Goo Chemical Company, Ltd. (Kyoto, Japan).

Polyacrylate-4 crosslinked polymer is a copolymer of sodium acryloyldimethyltaurate, dimethyl acrylamide, sodium acrylate, acrylic acid and hydroxyethylacrylate crosslinked with methylene bis-propenamide. This copolymer is commercially available under the brand Sepinov P500 from Seppic (Paris, France).

Polyacrylate-5 cross-linked polymer is commercially available under the trade name COSP23 from Miyoshi Kasei, Inc. (Urawa, Japan).

Polyacrylate-6 cross-linked polymer is a copolymer of acryloyldimethyl-ammonium taurate, dimethylacrylamide, lauryl methacrylate and laureth-4 methacrylate, cross-linked with trimethylolpropane triacrylate. This copolymer is commercially available under the brand name Sepimax Zen from Seppic Regulatory Affairs (Puteaux, France).

The cross-linked polyacrylate-7 polymer is a copolymer of PPG-6 phosphate methacrylate and one or more monomers of acrylic acid, methacrylic acid or a simple ester thereof, cross-linked with PEG dimethicone acrylate /PPG-25/29. This copolymer is commercially available under the trade name Y-17552 from Momentive Performance Materials (Friendly, W.Va.).

Polyacrylate-8 cross-linked polymer is a copolymer of t-butyl methacrylate, stearyl methacrylate, PEG-23 methoxy methacrylate and dimethylacrylamide, cross-linked with ethylene glycol dimethacrylate.

Polyacrylate-9 cross-linked polymer is a copolymer of t-butylaminoethyl methacrylate and carboxyethyl acrylate, cross-linked with a combination of pentaerythritol tetraacrylate and a hexafunctional acrylate formed by reacting pentaerythritol triacrylate with toluene diisocyanate .

Polyacrylate-10 cross-linked polymer is the cross-linked polymer prepared by polymerization of a mixture of trimethoxysilylpropyl methacrylate with trimethyloylpropane trimethacrylate.

Polyacrylate-11 cross-linked polymer is a polymer of methacrylic acid, acryloyl dimethyltaurate, and dimethylacrylamide, cross-linked with PPG-3 glyceryl triacrylate, and partially neutralized with ammonia. This copolymer is commercially available under the brand name Aristoflex Velvet from Clariant International Ltd. (Muttenz, Switzerland).

Polyacrylate-12 cross-linked polymer is a copolymer of t-butyl methacrylate, stearyl methacrylate, PEG-23 methoxy methacrylate and dimethylacrylamide, cross-linked with methylene bis-acrylamide.

Polyacrylate-14 cross-linked polymer is a copolymer of acrylic acid, lauryl methacrylate, cetyl methacrylate, stearyl methacrylate and phosphorylcholine glycol methacrylate, cross-linked with a pentaerythritol allyl ether. This copolymer is commercially available under the brand name Phosphomer ST610KC from KCl Ltd. (Seoul, South Korea).

According to certain embodiments, the composition according to the present invention comprises a crosslinked polyacrylate polymer chosen from crosslinked polymer of polyacrylate-1, crosslinked polymer of polyacrylate-2, crosslinked polymer of polyacrylate-3, crosslinked polymer of polyacrylate-4, crosslinked polymer of polyacrylate-5, cross-linked polymer of polyacrylate-6, cross-linked polymer of polyacrylate-7, cross-linked polymer of polyacrylate-8, cross-linked polymer of polyacrylate-9, cross-linked polymer of polyacrylate-10, cross-linked polymer of polyacrylate-11, cross-linked polymer of polyacrylate-12, cross-linked polymer of polyacrylate-14, and a combination thereof.

Preferably, the composition according to the present invention comprises one or more selected from cross-linked polyacrylate-1 polymer, cross-linked polyacrylate-6 polymer, cross-linked polyacrylate-9 polymer, and cross-linked polyacrylate-11 polymer.

More preferably, the composition according to the present invention comprises a water-soluble polymer with hydrophobic association chosen from crosslinked polymer of polyacrylate-6, copolymer of steareth-100/PEG-136/HDI, copolymer of PEG-240/HDI bis-decyltetradeceth ether 20 and a combination thereof.

If it is present, advantageously, the water-soluble polymer with hydrophobic association is present in an amount ranging from 0.1% by weight to 10% by weight, preferably from 0.5% by weight to 5% by weight, more preferably from 0.3% by weight to 3% by weight, relative to the total weight of the composition.

According to a particularly preferred embodiment, the present invention provides a composition in the form of an oil-in-water emulsion for the care of keratinous materials comprising, relative to the total weight of the composition:

(i) from 0.5% by weight to 5% by weight of ARACHIDYL ALCOHOOL (and) BEHENYL ALCOHOL (and) ARACHIDYL GLUCOSIDE;

(ii) from 0.5% by weight to 5% by weight of POLYGLYCERYL-6 DISTEARATE (and) JOJOBA ESTERS (and) CETYL ALCOHOL (and) POLYGLYCERYL-3 BEESWAX;

(iii) from 0.1% by weight to 2% by weight of a compound chosen from 2-oleamido-1,3-octadecanediol and ceramide NP;

(iv) from 1% by weight to 5% by weight of hydroxypropyl tetrahydropyrantriol; And

(v) from 0.3% by weight to 3% by weight of a water-soluble polymer with hydrophobic association chosen from crosslinked polyacrylate-6 polymer, steareth-100/PEG-136/HDI copolymer, PEG-240/copolymer HDI, bis-decyltetradeceth-20 ether, and a combination thereof.

Dosage form and process

The composition of the present invention is in the form of an oil-in-water emulsion.

The composition according to the present invention has a lamellar structure.

The term “lamellar structure” designates a liquid crystalline structure, or a swollen or non-swollen crystalline lamellar hydrate phase, with planar symmetry, comprising several amphiphilic bilayers arranged in parallel and separated by a liquid medium which is generally water. The lamellar structure shows a characteristic optical effect when observed under an optical microscope under 90˚ cross-polarized light with unique optical effects, as shown in Figures 1 and 2. If the unique optical effect was observed, this means that the lamellar structure is formed.

The composition of the present invention can be used for the care of keratinous materials.

According to the second aspect, the present invention provides a non-therapeutic method for caring for keratinous materials, comprising the application of the composition according to the first aspect of the present invention to the keratinous materials.

The following examples serve to illustrate the present invention without being of a limiting nature.

EXAMPLES

The main raw materials used, their trade names and suppliers are listed in Table 1.

INCI name Trade name Supplier PEG-240/HDI COPOLYMER BIS-DECYLTETRADECETH-20 ETHER ADEKANOL GT-730 ADEKA POLYACRYLATE CROSSPOLYMER-6 SEPIMAX ZEN SEPPIC GLYCERIN GLICENAT GC K MB OXITENO SODIUM DILAURAMIDOGLUTAMIDE LYSINE PELLICER LB-30G ASAHI KASEI PHENOXYETHANOL HISOLVE EPH TOHO CHEMICALS HYDROXYPROPYL TETRAHYDROPYRANTRIOL MEXORYL SCN CHIMEX (NOVEAL) ARACHIDYL ALCOHOL (and) BEHENYL ALCOHOL (and) ARACHIDYL GLUCOSIDE MONTANOV 202 SEPPIC POLYGLYCERYL-6 DISTEARATE (and) JOJOBA ESTERS (and) CETYL ALCOHOL (and) POLYGLYCERYL-3 BEESWAX EMULIUM MELLIFERA MB GATTEFOSSE 2-OLEAMIDO-1,3-OCTADECANEDIOL MEXANYL GZ NOVEAL CERAMIDE NP CERAMIDE III EVONIK GOLDSCHMIDT C15-19 ALKANE EMOGREEN L19 SEPPIC HEXYLDECANOL EUTANOL G 16 COGNIS GLYCERYL STEARATE (and) PEG-100 STEARATE ARLACEL 165 CRODA SODIUM HYDROXIDE CAUSTIC SODA 50% DOW

Examples of invention 1 And 2 and comparative examples 1 And 2

The compositions of examples of invention (EI.) 1 and 2 and comparative examples (EC.) 1 and 2 were prepared according to the quantities indicated in table 2. The quantity of each component is given in % by weight of the weight total of the composition containing it.

Components EI. 1 EI. 2 EC. 1 EC. 2 HYDROXYPROPYL TETRAHYDROPYRANTRIOL 3.15 3.15 3.15 3.15 PEG-240/HDI COPOLYMER BIS-DECYLTETRADECETH-20 ETHER 2 2 2 2 CROSS-LINKED POLYACRYLATE-6 POLYMER 0.2 0.2 0.2 0.2 ARACHIDYL ALCOHOL (and) BEHENYL ALCOHOL (and) ARACHIDYL GLUCOSIDE ¹⁾ 2 2 - 2 POLYGLYCERYL-6 DISTEARATE (and) JOJOBA ESTERS (and) CETYL ALCOHOL (and) POLYGLYCERYL-3 BEESWAX 2 2 - 2 GLYCERYL STEARATE (and) PEG-100 STEARATE - - 2 - 2-OLEAMIDO-1,3-OCTADECANEDIOL 1 - - - CERAMIDE NP - 1 - - C ALKANE _15-19 0.5 0.5 0.5 0.5 HEXYLDECANOL 1 1 1 1 SODIUM HYDROXIDE Up to pH 6 Up to pH6 Up to pH6 Up to pH6 GLYCERIN 5 5 5 5 SODIUM DILAURAMIDOGLUTAMIDE LYSINE 0.35 0.35 0.35 0.35 PHENOXYETHANOL 0.3 0.3 0.3 0.3 Water This 100 This 100 This 100 This 100

ARACHIDYL ALCOHOL (and) BEHENYL ALCOHOL (and) ARACHIDYL GLUCOSIDE 1): comprising 55% by weight of ARACHIDYL ALCOHOL, 30% by weight of BEHENYL ALCOHOL and 15% by weight of ARACHIDYL GLUCOSIDE.

POLYGLYCERYL-6 DISTEARATE (and) JOJOBA ESTERS (and) CETYL ALCOHOL (and) POLYGLYCERYL-3 BEESWAX: comprising 64% by weight of POLYGLYCERYL-6 DISTEARATE, 19% by weight of JOJOBA ESTERS, 8 .5% by weight of CETYL ALCOHOL and 8.5% by weight of POLYGLYCERYL-3 BEESWAX.

Preparation process:

The compositions listed above were prepared as follows, taking as an example the composition of Example of Invention 1:

1). Mix the ingredients for an aqueous phase (glycerin, sodium dilauramidoglutamide lysine, phenoxyethanol and water) with a homogenizer and heat to 70 °C.

2). Mix ARACHIDYL ALCOHOL (and) BEHENYL ALCOHOL (and) ARACHIDYL GLUCOSIDE, POLYGLYCERYL-6 DISTEARATE (and) JOJOBA ESTERS (and) CETYL ALCOHOL (and) POLYGLYCERYL-3 BEESWAX, 2-oleamido-1 ,3-octadecanediol C _15-19 alkane, hexyldecanol with a homogenizer to obtain a mixture and heat to 70 °C.

3). Introduce the mixture into the aqueous phase and maintain homogenization at 60 °C for 10 min to obtain an O/W emulsion.

4). Add the polymers (PEG-240/HDI COPOLYMER, BIS-DECYLTETRADECETH-20 ETHER, and CROSS-LINKED POLYACRYLATE-6 POLYMER) into the emulsion and homogenize for 10 min.

5). Transfer the emulsion to a disperser and cool the emulsion to room temperature, maintain stirring and add the hydroxypropyl tetrahydropyrantriol.

6). Adjust the pH value with sodium hydroxide to obtain the composition.

Assessment

Each composition of invention examples 1 and 2 and comparative examples 1 and 2 was evaluated in terms of lamellar structure, skin barrier function and skin finish.

Lamellar structure

The possible formation of a lamellar structure was evaluated as follows.

The compositions were observed using a Leica DLMB microscope under 90˚ cross-polarized light, and microscopic photos were taken. If optical effects characteristic of the lamellar structure have been observed, this means that the lamellar structure has been formed.

There shows a photo of the composition of invention example 1 (EI.1) taken with a polarized light microscope.

There shows a photo of the composition of invention example 2 (EI.2) taken with a polarized light microscope.

Skin finish

The skin finish that each composition of invention Examples 1 and 2 and Comparative Examples 1 and 2 will deliver was evaluated by inviting 10 Chinese female volunteers to apply each composition to their face and rate the skin finish on a scale of 1 to 5 and on average, where 1 represents a very oily skin finish and 5 a very fresh skin finish. The 10 volunteers indicated the skin finish score 10 minutes after application.

The results of the lamellar structure of each composition prepared above and the skin finish delivered are indicated in Table 3.

Point EI. 1 EI. 2 EC. 1 EC. 2 lamellar structure YES YES YES YES Skin finish 4 4 2 3

NA: not observed.

Transepidermal water loss (TEWL)

The transepidermal water loss (TEWL) for the compositions of invention examples 1 and 2 and comparative examples 1 and 2 as well as for a commercial product (La Mer concentrated serum from the company Estee Lauder) was determined with a vapometer on the forearms of 6 female volunteers aged 18 to 40 years as follows.

18 µL (2 mg/cm ² ) of each tested sample was transferred and spread gently and evenly over each 3*3 cm ² test area. Transepidermal water loss (TEWL) obtained from an untreated area was used as a blank control.

Lower TEWL indicates better skin barrier function.

The results are summarized in Table 4.

Properties EI.1 EI. 2 EC. 1 EC. 2 Commercial product Blank witness TEWL (8h, %) -45.39 -38.50 -31.75 -32.20 -27.63 -0.45

It can be seen that the compositions of examples of invention 1 and 2 deliver a better skin barrier function compared to the compositions of comparative examples 1 and 2 and of the commercial product.

Claims (10)

Composition in the form of an oil-in-water emulsion for the care of keratinous materials, comprising:
(i) at least one nonionic surfactant chosen from sugar ethers of C ₈ -C ₂₂ fatty alcohols;
(ii) at least one nonionic ester-type surfactant comprising a combination of at least one monounsaturated ester and at least one polyglyceryl diester; And
(iii) at least one ceramide type compound. Composition according to claim 1, in which the sugar ethers are alkylpolyglucosides having a formula (I) of:
R(O)(G) _n (I)
in which :
R is a linear or branched C _8-22 alkyl, preferably a C _8-16 alkyl;
G is a residue of a sugar selected from the group consisting of glucose, dextrose, fructose, galactose, sucrose, ribose, lactose, maltose, xylose, mannose, cellulose dextran or starch; And
n ranges from 1 to 5, preferably from 1.05 to 2. Composition according to claim 2, in which the alkylpolyglucoside is used in mixture with a fatty alcohol having 8 to 30 carbon atoms, for example 10 to 20 carbon atoms, in which the alkylpolyglucoside and the fatty alcohol have atoms of similar carbon with a difference less than 5, or less than 2, or worth 0. Composition according to claim 3, in which the mixture of alkylpolyglucoside with the fatty alcohol is chosen from: myristyl alcohol/myristyl glucoside, isostearyl alcohol/isostearyl glucoside, cetylstearyl alcohol/cetylstearyl glucoside, cetylstearyl alcohol/coconut glucoside, arachidyl alcohol/alcohol behenyl/arachidyl glucoside, C _14-22 alcohol/C _14-22 alkyl glucoside, and coconut alcohol/coconut glucoside. Cosmetic composition according to any one of claims 1 to 4, in which the nonionic ester-type surfactant comprises:
i) at least one monounsaturated ester of formula (II),
R1-C(O)-O-R2 (II)
in which :
R1 and R2 represent, respectively, a C ₁₈ to C ₄₄ fatty chain, at least one of R1 or R2 is monounsaturated; And
ii) at least one polyglyceryl diester of formula (III),
R3-C(O)-(O-CH ₂ -CH(OH)-CH ₂ ) _n -OC(O)-R4 (III)
in which :
R3 and R4 represent, respectively, a saturated C ₁₈ to C ₄₄ fatty chain, linear or branched,
preferably, the nonionic ester type surfactant comprises at least one monounsaturated ester of formula (II) in which R1 and R2 represent, respectively, a C ₁₈ -C ₃₀ fatty chain, and at least one of R1 or R2 is monounsaturated; and at least one polyglyceryl diester of formula (III) in which R3-C(O)- and R4 each represent a saturated C ₂₀ -C ₃₄ fatty chain, linear or branched,
more preferably, the ester-type nonionic surfactant is a mixture of polyglyceryl-6 distearate, jojoba esters, polyglyceryl-3 beeswax and cetyl alcohol. Composition according to any one of claims 1 to 5, in which the ceramide type compound corresponds to general formula (I):

in which :
- R ₁ designates:
- either a hydrocarbon radical in C ₁ -C ₅₀ , preferably in C ₅ -C ₅₀ , saturated or unsaturated and linear or branched, this radical being able to be substituted by one or more hydroxyl groups optionally esterified with an acid R ₇ COOH, R ₇ being a C ₁ -C ₃₅ hydrocarbon radical optionally mono- or polyhydroxylated, saturated or unsaturated and linear or branched, the hydroxyl(s) of the R ₇ radical being able to be esterified by a C ₁ -C ₃₅ fatty acid, saturated or unsaturated , linear or branched, optionally mono- or polyhydroxylated;
- either a radical R''-(NR-CO)-R', in which R denotes a hydrogen atom or a mono or polyhydroxylated C ₁ -C ₂₀ hydrocarbon radical, preferably monohydroxylated, R' and R'' are hydrocarbon radicals whose sum of carbon atoms is between 9 and 30, R' being a divalent radical;
- either a radical R ₈ -O-CO-(CH ₂ ) _p , in which R ₈ designates a C ₁ -C ₂₀ hydrocarbon radical and p is an integer varying from 1 to 12;
- R ₂ is chosen from a hydrogen atom, a saccharide type radical, in particular a (glycosyl) _n , (galactosyl) _m or sulfogalactosyl radical, a sulfate or phosphate residue, a phosphorylethylamine radical and a phosphorylethylammonium radical, in which n is an integer varying from 1 to 4 and m is an integer varying from 1 to 8;
- R ₃ designates a hydrogen atom or a C ₁ -C ₃₃ hydrocarbon radical, hydroxylated or not, saturated or unsaturated, the hydroxyl(s) being able to be esterified by an inorganic acid or an acid R ₇ COOH, R ₇ having the same meanings as above, and the hydroxyls can be etherified by a (glycosyl) _n , (galactosyl) _m , sulfogalactosyl, phosphorylethylamine or phosphorylethylammonium radical, R ₃ can also be substituted by one or more C ₁ -C ₁₄ alkyl radicals. ;
preferably, R ₃ denotes a C ₁₅ -C ₂₆ α-hydroxyalkyl radical, the hydroxyl group being optionally esterified with a C ₁₆ -C ₃₀ α-hydroxyacid;
- R ₄ designates a hydrogen atom, a methyl or ethyl radical, a C ₃ -C ₅₀ hydrocarbon radical, saturated or unsaturated, linear or branched, optionally hydroxylated or a -CH ₂ -CHOH-CH ₂ -OR ₆ radical , in which R ₆ designates a C ₁₀ -C ₂₆ hydrocarbon radical, or a R ₈ -O-CO-(CH ₂ ) _p radical, in which R ₈ designates a C ₁ -C ₂₀ hydrocarbon radical and p is a integer varying from 1 to 12;
- R ₅ designates a hydrogen atom or a C ₁ -C ₃₀ hydrocarbon radical, saturated or unsaturated, linear or branched, optionally mono or polyhydroxylated, the hydroxyl(s) being able to be etherified by a radical (glycosyl) _n , (galactosyl ) _m , sulfogalactosyl, phosphorylethylamine or phosphorylethylammonium;
provided that when R ₃ and R ₅ represent hydrogen or when R ₃ represents hydrogen and R ₅ represents methyl, then R ₄ does not represent a hydrogen atom or a methyl or ethyl radical. Composition according to any one of claims 1 to 5, in which the ceramide type compound is chosen from:
- 2-N-linoleoylaminooctadecane-1,3-diol,
- 2-N-oleoylaminooctadecane-1,3-diol,
- 2-N-palmitoylaminooctadecane-1,3-diol,
- 2-N-stearoylaminooctadecane-1,3-diol,
- 2-N-behenoylaminooctadecane-1,3-diol,
- 2-N-[2-hydroxypalmitoyl]aminooctadecane-1,3-diol,
- 2-N-stearoylaminooctadecane-1,3,4-triol, and in particular N-stearoylphytosphingosine,
- 2-N-palmitoylaminohexadecane-1,3-diol,
and a combination of these. Composition according to any one of claims 1 to 7, further comprising a water-soluble polymer with a hydrophobic association chosen from nonionic associative polyethers-polyurethanes, crosslinked polyacrylate polymers, and a combination thereof. Composition according to claim 1, comprising, relative to the total weight of the composition:
(i) from 0.5% by weight to 5% by weight of ARACHIDYL ALCOHOLS (and) BEHENYL ALCOHOL (and) ARACHIDYL GLUCOSIDE;
(ii) from 0.5% by weight to 5% by weight of POLYGLYCERYL-6 DISTEARATE (and) JOJOBA ESTERS (and) CETYL ALCOHOL (and) POLYGLYCERYL-3 BEESWAX;
(iii) from 0.1% by weight to 2% by weight of a compound chosen from 2-oleamido-1,3-octadecanediol and ceramide NP;
(iv) from 1% by weight to 5% by weight of hydroxypropyl tetrahydropyrantriol; And
(v) from 0.3% by weight to 3% by weight of a water-soluble polymer with hydrophobic association chosen from crosslinked polyacrylate-6 polymer, steareth-100/PEG-136/HDI copolymer, PEG-240/copolymer HDI, bis-decyltetradeceth-20 ether, and a combination thereof. Non-therapeutic process for caring for keratinous materials, comprising the application of the composition according to any one of claims 1 to 9 on the keratinous materials.