Composition for the care of keratinous materials

The composition of an oil-in-water emulsion, containing specific non-ionic surfactants and ceramides, addresses the issue of greasiness in skin care products by enhancing skin barrier function while maintaining a non-greasy skin finish.

FR3134007B1Active Publication Date: 2025-05-02LOREAL SA
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Patent Information

Application Number
FR2022003972
Authority / Receiving Office
FR · FR
Patent Type
Patents
Current Assignee / Owner
Priority Date
2022-03-30
Filing Date
2022-04-28
Publication Date
2025-05-02
Estimated Expiration
2042-04-28

AI Technical Summary

Technical Problem

Existing skin care products that aim to improve the skin barrier function often result in a greasy feel, which is undesirable.

Method used

A composition in the form of an oil-in-water emulsion for the care of keratinous materials, comprising at least a non-ionic surfactant chosen from sugar ethers of fatty alcohols, a combination of monounsaturated esters and diesters of polyglyceryle, and at least one ceramide type compound, which forms a lamellar structure or liquid crystals, providing a non-greasy skin finish.

Benefits of technology

The composition effectively improves the skin barrier function without leaving a greasy residue, maintaining the skin's natural hydration and elasticity.

✦ Generated by Eureka AI based on patent content.
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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 selected from C8-C22 fatty alcohol sugar ethers; (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 present invention also relates to a non-therapeutic method for the care of keratinous materials, comprising the application of said composition to the skin. Figure for the abstract: Figure 1
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Description

Title of the invention: composition for the care of keratinous materials Technical field

[0001] 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 method for the care of keratinous materials. context of art

[0002] 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 injuries, microorganisms, and ultraviolet damage. The health and appearance of the skin can, however, deteriorate due to environmental factors, genetics, makeup, diet, and sun exposure. With aging, the outer layer of the skin (epidermis) thins, although the number of cell layers remains unchanged. In contrast, the number of pigment-containing cells (melanocytes) decreases. As a result, the skin appears pale and translucent. Large pigmented spots (age spots, senile spots, or lentigines) may appear in sun-exposed areas. Changes in connective tissue reduce the skin's strength and elasticity.This phenomenon is known as elastosis. It is most visible in areas exposed to the sun (solar elastosis). Elastosis gives the skin the parched, weather-worn appearance seen 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, rashes, and swelling.

[0003] Ceramides are a group of natural waxy, fatty substances found in the skin, composed of sphingosine and lipids (fatty acids) bound together. Ceramides make up about 50% of all skin lipids and are made in the lower living cells of the epidermis. As the cells mature and move to the surface, ceramides are released into the topmost 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 and sheeted array between the dead cells. Ceramides and cholesterol protect the skin from moisture loss, which which helps keep it youthful and supple, and support the skin matrix, keeping it firm. Young individuals produce enough ceramides and cholesterol to keep skin healthy. However, with aging, the production of ceramides and cholesterol decreases, and the skin begins to sag and wrinkle.

[0004] In order to achieve stabilization and restorative efficacy, improvement of the skin barrier function is an essential parameter, which means that transepidermal water loss (TEWL) should be a good attribute to characterize the barrier function. However, normal products with superior TEWL results generally deliver a greasy feel.

[0005] There is therefore a need to formulate a composition for skin care, which can improve the barrier function of the skin without a greasy feeling. Summary of the invention

[0006] The inventors have now discovered that it is possible to formulate a skin care composition, which can improve the skin barrier function without a greasy feeling.

[0007] Accordingly, 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:

[0008] (i) at least one non-ionic surfactant chosen from fatty alcohol sugar ethers in Cg-C22;

[0009] (ii) at least one non-ionic ester surfactant comprising a combination of at least one monounsaturated ester and at least one polyglyceryl diester; and

[0010] (iii) at least one ceramide-type compound.

[0011] 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.

[0012] The inventors have found that the composition of the present invention has a lamellar or liquid crystal structure.

[0013] The composition of the present invention can provide good skin barrier function and a non-greasy skin finish.

[0014] According to a second aspect, the present invention provides a non-therapeutic method for caring for keratinous materials, comprising applying the composition according to the first aspect of the present invention to the keratinous materials.

[0015] Other advantages of the present invention will appear more clearly on reading the description and examples which follow. Brief description of the drawings

[0016] Implementations of the present invention will now be described, by way of example. example only, with reference to the attached figures, in which:

[0017] [Fig.l] [Fig.l] shows a photograph of the composition of Invention Example 1 (ELI) taken with a polarized light microscope.

[0018] [Fig.2] [Fig.2] shows a photograph of the composition of the invention example 2 (EI.2) taken with a polarized light microscope. DETAILED DESCRIPTION OF THE INVENTION

[0019] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which the present invention pertains. 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 shall apply.

[0020] In the following 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 ...".

[0021] Furthermore, the expression "at least one" used in the present description is equivalent to the expression "one or more".

[0022] In the present application, the term "comprising" should be interpreted as encompassing all optionally mentioned features, as well as optional, additional and unspecified features. In the present document, the use of the term "comprising" also discloses the embodiment in which no features other than the specifically mentioned features are present (i.e., "consisting of").

[0023] Unless otherwise indicated, all numerical values ​​expressing the amount of ingredients and the like which are used in the description and claims are to be understood as being modified by the term "about". Accordingly, unless otherwise indicated, the numerical values ​​and parameters described herein are approximate values ​​which may be modified according to the intended purpose, if necessary.

[0024] For the purposes of the present invention, the term "keratinous materials" is intended to cover human skin, mucous membranes such as the lips. Facial skin is more particularly considered according to the present invention.

[0025] All percentages in the present invention refer to percentages by weight, unless otherwise indicated.

[0026] 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:

[0027] (i) at least one non-ionic surfactant chosen from fatty alcohol sugar ethers in C8-C22;

[0028] (ii) at least one non-ionic ester surfactant comprising a combination of at least one monounsaturated ester and at least one polyglyceryl diester; and

[0029] (iii) at least one ceramide-type compound.

[0030] Nonionic surfactants chosen from sugar ethers of Cg-Qz fatty alcohols

[0031] According to the first aspect, the present invention comprises at least one non-ionic surfactant chosen from sugar ethers of C8-C22 fatty alcohols

[0032] Among the sugar ethers, mention may in particular be made of alkylpolyglucosides (APG). An alkylpolyglucoside may be used alone or in the form of a mixture of two or more alkylpolyglucosides. An alkylpolyglucoside generally has a formula (I) of:

[0033] R(O)(G)n (I)

[0034] in which:

[0035] R is a linear or branched C8-22 alkyl, preferably a Cx-16 alkyl; G is a residue of a sugar; and n is from 1 to 5, preferably from 1.05 to 2.

[0036] 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.

[0037] Alkylpolyglucosides useful according to the present invention include, for example,

[0038] - decylglucoside, for example the product sold under the name Mydol 10 by the Kao Chemicals company, the product sold under the name Plantaren 2000 by Henkel company, and the product sold under the name Oramix NS 10 by SEPPIC company;

[0039] - caprylic / capric glucoside, for example the product sold under the name mination Oramix CG 110 by the company SEPPIC or under the name Lutensol GD 70 by the company BASF;

[0040] - laurylglucoside, for example products sold under the names Plantaren 1200 N and Plantacare 1200 by Henkel;

[0041] - coco glucoside, for example the product sold under the name Plantacare 818 / UP by Henkel company;

[0042] - cetostearyl glucoside optionally in admixture 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;

[0043] - arachidyl glucoside.

[0044] According to one embodiment of the present invention, the APG may be used in a 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 mixture, the alkylpolyglucoside and the fatty alcohol have similar carbon atoms, for example, with a difference of less than 5, in particular less than 3, or less than 2. More preferably, the alkylpolyglucoside and the fatty alcohol used in the mixture have the same carbon atoms. For example, the alkylpolyglucoside and the fatty alcohol of the mixture may have the same alkyl moiety.

[0045] Alkylpolyglucoside / fatty alcohol mixtures are known in the art, see, for example, WO 9847610 and WO 9513863.

[0046] Examples of alkylpolyglucoside / fatty alcohol mixtures may include products sold under the Montanov series name by the company SEPPIC:

[0047] - myristyl alcohol / myristyl glucoside: Montanov 14;

[0048] - isostearyl alcohol / isostearyl glucoside: Montanov WO 18.

[0049] - cetylstearyl alcohol / cetylstearyl glucoside: Montanov 68;

[0050] - cetylstearyl alcohol / coco glucoside: Montanov 82;

[0051] - arachidyl alcohol / behenyl alcohol / arachidyl glucoside: Montanov 202;

[0052] - C14.22 alcohol / C14.22 alkyl glucoside: Montanov L; and

[0053] - coconut alcohol / coconut glucoside: Montanov S.

[0054] Other useful APGs may include, for example: decyl glucoside and lauryl glucoside, sold, for example, by Henkel under the respective names Plantaren 2000 and Plantaren 1200. Furthermore, a mixture of cetostearyl glucoside with cetostearyl alcohol, in addition to Montanov 68, is also sold, for example, under the name Tegocare CG90 by Goldschmidt and under the name Emulgade KE3302 by Henkel.

[0055] Advantageously, the non-ionic surfactant chosen from sugar ethers of C8-C22 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. Ester-type non-ionic surfactant

[0056] According to the first aspect, the composition according to the present invention comprises at least one non-ionic surfactant of ester type comprising a combination of at least one monounsaturated ester and at least one polyglyceryl diester.

[0057] Preferably, the ester-type non-ionic surfactant comprises:

[0058] i) at least one monounsaturated ester of formula (II),

[0059] R1-C(O)-O-R2 (II)

[0060] in which:

[0061] RI and R2 represent, respectively, a C[8 to C44] fatty chain, at least one of RI or R2 is monounsaturated; and

[0062] ii) at least one polyglyceryl diester of formula (III),

[0063] R3-C(O)-(O-CH2-CH(OH)-CH2)nOC(O)-R4 (III)

[0064] in which:

[0065] R3 and R4 represent, respectively, a linear or branched saturated C[8 to C44] fatty chain.

[0066] More specifically, in formula (II), RI and R2 respectively represent a C18-C40 fatty chain, more preferably a C18-C30 fatty chain. At least one of RI or R2 is monounsaturated.

[0067] More particularly, in formula (II), the Rl-C(O)- group corresponds to the carbon chain of the fatty acid. This chain may be linear or monounsaturated, and comprises at least 18 carbon atoms. Examples of unsaturated acids include oleic acid (C18:1), ga-doleic acid (C20:1), erucic acid (C22:1), up to hexaconenoic acid (C26:1). The Rl-C(O)- group may also consist of branched and saturated acids of at least 18 carbon atoms, also called Guerbet acids. The R2-O- group may consist of linear monounsaturated fatty alcohols of at least 18 carbon atoms. Examples of unsaturated acids include octadecenol, eicosenol, docosenol and hexacosenol. The carbon chain of the alcohol can also be branched and saturated and have at least 18 carbon atoms. Such alcohols are also called Guerbet alcohols.

[0068] Preferably, the monounsaturated ester of formula (II) is a mixture of esters comprising different fatty chain lengths in their structures. More preferably, such a monounsaturated ester is liquid at room temperature.

[0069] Mention may be made, as a preferred monounsaturated ester, for example, of 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 in C18:1 (preferably minor), C20:1 and C22:1 (preferably major with C20:1>C22:1), with unsaturated fatty alcohols in C20:1, C22:1 and C24:1.

[0070] Preferably, in formula (III), the group R3-C(O)- corresponds to the carbon chain of a C[8 to C44 fatty acid, said acid being generally linear and saturated, preferably corresponds to a linear and saturated C20 to C34 fatty acid. This therefore includes eicosanoic (or arachidic) acid (C20), docosanoic (or behenic) acid (C22), tetracosanoic (or lignoceric) acid (C24), hexacosanoic (or cerotic) acid (C26). The group R4 corresponds to the hydrocarbon chain of the alcohol, said alcohol being generally linear saturated and having a chain from C18 to C^, preferably from C20 to C34. n is an integer between 2 and 6.

[0071] According to the present invention, the polyglyceryl diester is obtained by esterification of a solid wax in the presence of at least one polyol.

[0072] Solid waxes suitable for obtaining polyglyceryl diester have a melting point between 50 and 90 °C. They correspond to mixtures essentially comprising monoesters having the formula R'-C(O)-O-R2, where the R'-C(O)- group 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 (C20), docosanoic (or behenic) acid (C22), tetracosanoic (or lignoceric) acid (C24), hexacosanoic (or cerotic) acid (C26). Depending on the origin of the wax, the mixture of monoesters 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 R2 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 most preferably 34. Preferably, said alcohol is eicosanol, docosanol or tetracosanol. Beeswax, camauba wax, candelilla wax, rice bran wax, sunflower wax, ouricury wax, Shellac wax and sugarcane wax are examples of natural solid waxes.

[0073] Preferably, the solid wax suitable for the esterification reaction is beeswax.

[0074] Preferably, the polyol used for the esterification is selected from the group consisting of ethylene glycol, diethylene glycol, triethylene glycol, 2-methyl pro-panediol, propylene glycol, butylene glycol, neopentyl glycol, hexylene glycol, octylene glycol, polyethylene glycol, polypropylene glycol, trimethylolpropane, sorbitol, erythritol, pentaerythritol, dipentaerythritol, glycerol, diglycerol and poly-glycerol (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.

[0075] The non-ionic ester surfactant also comprises the acid portion of a solid wax. Waxes have a complex composition. They have the common characteristic of containing a mixture of monoesters of very long chain fatty acids and alcohols.

[0076] Preferably, the non-ionic 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.

[0077] Preferred catalysts are alkali or alkaline earth hydroxides or alkoxides, calcium hydroxide, potassium or sodium carbonates or tin or titanium based catalysts.

[0078] Preferably, the solid wax is advantageously chosen from the group comprising Camauba wax, candelilla wax, rice bran wax, sunflower wax, sugarcane wax, ouricury wax, beeswax and Shellac wax.

[0079] 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.

[0080] 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 esters of formulae (II) and (III) / polyol mass ratio 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.

[0081] Preferably, the ester-type non-ionic surfactant comprises a diester of a C14-C22 fatty acid with a polyglycerol.

[0082] Typically, the C14-C22 fatty acid may be selected from the group of myristic, stearic, isostearic, palmitic, oleic, behenic, erucic and ara-chidic acids, and mixtures thereof.

[0083] 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.

[0084] Preferably, said diester is a diester of distearic acid with hexaglycerol. Preferably, it is polyglyceryl-6 distearate.

[0085] According to a particular embodiment of the present invention, the non-ionic surfactant of ester type according to the present invention is present with at least one fatty alcohol comprising from 10 to 30 carbon atoms.

[0086] Examples of fatty alcohols that can be used include 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 material (tallow, etc.). Preferably, a fatty alcohol comprising from 20 to 26 carbon atoms, preferably from 10 to 24 carbon atoms and more preferably from 12 to 22 carbon atoms is used.

[0087] 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.

[0088]

[0089]

[0090]

[0091]

[0092]

[0093] 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 polyglyceryl-3 beeswax (INCI name: Poly-glyceryl-6 Distearate (and) Jojoba Esters (and) Polyglyceryl-3 Beeswax (and) Cetyl Alcohol). Said mixture comprises from 5 to 30% by weight of the total weight of the mixture of jojoba wax; from 3 to 15% by weight of cetyl alcohol; at least 50% by weight of polyglyceryl-6 distearate; and from 3 to 15% by weight of polyglyceryl-3 beeswax. Advantageously, the non-ionic surfactant of ester type 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 type 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 incorporated herein by reference. The ceramide-type compounds which can be used according to the present invention preferably correspond to the general formula (I):

[0094]

[0095]

[0096] in which: - Ri represents: - either a C1-C50, preferably C5-C50, saturated or unsaturated and linear or branched hydrocarbon radical, this radical possibly being substituted by one or more hy- groups droxyls optionally esterified by an acid R7COOH, R7 being a C1-C35 hydrocarbon radical optionally mono- or polyhydroxylated, saturated or unsaturated and linear or branched, the hydroxyl(s) of the radical R7 possibly being esterified by a C1-C35 fatty acid, saturated or unsaturated, linear or branched, optionally mono- or polyhydroxylated;

[0097] - either a radical R”-(NR-CO)-R', in which R denotes a hydrogen atom or a mono- or polyhydroxylated C1-C2o hydrocarbon radical, preferably mono-hydroxylated, R' and R' ' are hydrocarbon radicals whose sum of carbon atoms is between 9 and 30, R' being a divalent radical;

[0098] - either a radical R8-O-CO-(CH2)P, in which R8 denotes a hydrocarbon radical in CrC2o and p is an integer ranging from 1 to 12;

[0099] - R2 is chosen from a hydrogen atom, a saccharide-type radical, in particular 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 ranging from 1 to 4 and m is an integer ranging from 1 to 8;

[0100] - R3 denotes a hydrogen atom or a hydroxylated C1-C33 hydrocarbon radical or not, saturated or unsaturated, the hydroxyl(s) being able to be esterified by an inorganic acid or an acid R7COOH, R7 having the same meanings as above, and the hydroxyl(s) being able to be etherified by a (glycosyl)n, (galactosyl)m, sulfogalactosyl, phosphorylethylamine or phosphorylethylammonium radical, R3 also being able to be substituted by one or more CrCi4 alkyl radicals;

[0101] preferably, R3 denotes a C15-C26 α-hydroxyalkyl radical, the hydroxyl group being optionally esterified by a C16-C30 α-hydroxy acid;

[0102] - R4 denotes a hydrogen atom, a methyl or ethyl radical, a hy radical C3-C5o hydrocarbon radical, saturated or unsaturated, linear or branched, optionally hydroxylated or a radical -CH2-CHOH-CH2-O-R6, in which R6 denotes a C10-C26 hydrocarbon radical, or a radical R8-O-CO-(CH2)P, in which R8 denotes a C1C2o hydrocarbon radical and p is an integer ranging from 1 to 12;

[0103] - R5 denotes a hydrogen atom or a saturated or CrC3o hydrocarbon radical unsaturated, linear or branched, optionally mono or polyhydroxylated, the hydroxyl(s) being able to be etherified by a (glycosyl)n, (galactosyl)m, sulfogalactosyl, phosphorylethylamine or phosphorylethylammonium radical;

[0104] provided that when R3 and R5 represent hydrogen or when R3 represents hydrogen and R5 represents methyl, then R4 does not represent a hydrogen atom or a methyl or ethyl radical.

[0105] Among the compounds of formula (I), preferred are 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, the teachings of which are incorporated herein by reference.

[0106] The ceramide-type compounds more particularly preferred according to the invention are the compounds of formula (I) for which Ri denotes an alkyl derived from C14-C22 fatty acids, saturated or unsaturated, optionally hydroxylated; R2 denotes a hydrogen atom; and R3 denotes a linear Cn-Cp radical and preferably C13-C15, optionally hydroxylated. R3 preferably denotes an α-hydroxycetyl radical and R2, R4 and R5 denote a hydrogen atom.

[0107] Such compounds are for example:

[0108] - 2-N-linoleoylaminooctadecane-1,3-diol,

[0109] - 2-N-oleoylaminooctadecane-1,3-diol (N-oleoyldihydrosphingosine),

[0110] - 2-N-palmitoylaminooctadecane-1,3-diol,

[0111] - 2-N-stearoylaminooctadecane-1,3-diol,

[0112] - 2-N-behenoylaminooctadecane-1,3-diol,

[0113] - 2-N-[2-hydroxypalmitoyl]aminooctadecane-1,3-diol,

[0114] - 2-N-stearoylaminooctadecane-1,3,4-triol and in particular N- stearoylphytosphingosine,

[0115] - 2-N-palmitoylaminohexadecane-1,3-diol,

[0116] or mixtures of these compounds.

[0117] Specific mixtures may also be used, such as, for example, mixtures of ceramide(s) 2 and ceramide(s) 5 according to the Downing classification.

[0118] It is also possible to use the compounds of formula (I) for which R 1 denotes an alkyl radical derived from saturated or unsaturated C12-C22 fatty acids; R 2 denotes a galactosyl or sulfogalactosyl radical; and R 3 denotes a saturated or unsaturated C12-C22 hydrocarbon radical and preferably a CH=CH-(CH 2) i 2 -CH 3 group.

[0119] An example of this is the product composed of a mixture of glycoceramides sold under the trade name Glycocer by Waitaki International Biosciences.

[0120] 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.

[0121] These compounds are, for example, Questamide H (bis(N hydroxyethyl-N-cetyl)malonamide), sold by Quest, or cetyl acid N-(2-hydroxyethyl)-N-(3-cetyloxy-2-hydroxy-propyl)amide.

[0122] N-docosanoyl-N-methyl-D-glucamine, described in patent application WO 94 / 24097, can also be used.

[0123] Most preferably, the ceramide may be chosen from 2-oleamido-l,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.

[0124] 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 from 0.1% by weight to 2% by weight, relative to the total weight of the composition. Aqueous phase

[0125] As an oil-in-water emulsion, the cosmetic composition of the present invention comprises a continuous aqueous phase.

[0126] Said aqueous phase comprises water.

[0127] 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 the total weight of the composition. Oily phase

[0128] As an oil-in-water emulsion, the composition of the present invention comprises at least one dispersed oily phase.

[0129] Said fatty phase preferably comprises at least one oil.

[0130] The oil may be volatile or non-volatile.

[0131] The term "oil" denotes a non-aqueous, water-immiscible compound which is liquid at room temperature (25°C) and atmospheric pressure (760 mmHg). The term "non-volatile oil" denotes 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 103 mmHg (0.13 Pa). A non-volatile oil can also be defined as having an evaporation rate such that, under the conditions defined above, the amount evaporated after 30 minutes is less than 0.07 mg / cm2.

[0132] These oils can be of vegetable, mineral or synthetic origin.

[0133] Said oils can be chosen from hydrocarbon, silicone or fluorinated oils.

[0134] 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 F heteroatoms. Such an oil may contain alcohol, ester, ether, carboxylic acid, amine and / or amide groups.

[0135] The term “silicone oil” designates an oil containing at least one silicon atom, notably containing Si-O groups.

[0136] The term “fluorinated oil” designates an oil containing at least one fluorine atom.

[0137] Advantageously, the oily phase is present in an amount ranging from 0.5% in 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

[0138] The composition of the present invention may comprise an additional cosmetic active ingredient in addition to the ceramide compound.

[0139] As an example of cosmetic active ingredient, mention may be made of 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 thereof; 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, yeasts and bacteria; enzymes; agents acting on microcirculation, etc.

[0140] It is easy for a person skilled in the art to adjust the amount of the additional cosmetic active ingredient depending on the final use of the composition according to the present invention.

[0141] Preferably, the composition of the present invention comprises a cosmetic active compound chosen from C-glycosides of formula (V): (V)

[0142] in which:

[0143] - R represents a C 1 to C 10 alkyl radical, in particular C 1 to C 4 , saturated which may optionally be substituted by at least one radical chosen from OH, COOH or COOR” 2, with R”2 being a saturated C1-C4 alkyl radical,

[0144] - 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 possibly being substituted by a necessarily free hydroxyl group and optionally one or more optionally protected amine functional groups, and

[0145] - X represents a radical chosen from the groups -CO-, -CH(OH)-, -CH(NH2)-, - CH(NHCH2CH2CH2OH)-, -CH(NHPh)- and -CH(CH3)- and in particular a radical -CO-, -CH(OH)- or -CH(NH2)- and more particularly a radical -CH(OH)-,

[0146] the S-CH2-X bond represents a bond of anomeric nature C, which can be a or [3, as well as their physiologically acceptable salts, their solvates, such as hydrates, and their optical and geometric isomers.

[0147] The C-glycosides of formula (V) useful for implementing the invention are in particular those for which R denotes a saturated linear alkyl radical of C1 to C6, in particular C1 to C4, preferentially C1 to C2, and more preferentially a methyl radical.

[0148] Among the alkyl groups suitable for implementing the invention, mention may in particular be made of methyl, ethyl, isopropyl, n-propyl, n-butyl, t-butyl, isobutyl, sec-butyl, pentyl, n-hexyl, cyclopropyl, cyclopentyl or cyclohexyl groups.

[0149] According to one embodiment of the invention, it is possible to use a C-glycoside compound corresponding to formula (V) for which S can represent a monosaccharide or a polysaccharide comprising up to 6 sugar units, in the form of pyranose and / or furanose and of L and / or D series, 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 moreover retaining all the definitions given above.

[0150] Advantageously, a monosaccharide of the invention may be chosen from D-glucose, D-galactose, D-mannose, D-xylose, D-lyxose or L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D-glucosamine or N-acetyl-D-galactosamine and advantageously denotes D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose and in particular D-xylose.

[0151] More particularly, a polysaccharide of the invention comprising up to 6 sugar units may 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 may advantageously be chosen from xylobiose, methyl-[3-xylobioside, xylotriose, xylotetraose, xylopentaose and xylohexaose and in particular xylobiose, which is composed of two xylose molecules linked by a 1-4 bond.

[0152] 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.

[0153] Preferably, a C-glycoside derivative of formula (V) is used for which:

[0154] - R represents a linear unsubstituted C1-C4, in particular C1-C2, alkyl radical, in particular a methyl radical;

[0155] - 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;

[0156] - X represents a group chosen from -CO-, -CH(OH)- or -CH(NH2)- and preferably a CH(OH)- group.

[0157] Acceptable salts of the compounds described in the present invention include conventional non-toxic salts of said compounds, such as those formed from acids organic or inorganic. Examples include salts of inorganic acids, such as sulfuric acid and hydrochloric acid. Also included are salts of organic acids, which may contain one or more carboxylic, sulfonic or phosphonic acid groups. Particular examples include propionic acid, acetic acid, terephthalic acid, citric acid and tartaric acid.

[0158] When the compound of formula (V) comprises an acid group, the neutralization of the acid group(s) may be carried out with an inorganic base, such as LiOH, NaOH, KOH, Ca(OH)2, NH4OH, 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 comprise one or more nitrogen and / or oxygen atoms and may thus comprise, for example, one or more alcohol functions; in particular, 2-amino-2-methylpropanol, triethanolamine, 2-(dimethylamino)propanol or 2-amino-2-(hydroxymethyl)-1,3-propanediol may be mentioned. Lysine or 3-(dimethylamino)propylamine may also be mentioned.

[0159] 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. Examples include solvates due to the presence of water or linear or branched alcohols, such as ethanol or isopropanol.

[0160] Of course, according to the invention, a C-glycoside derivative corresponding to formula (V) can be used alone or in a mixture with other C-glycoside derivatives and in any proportion.

[0161] A C-glycoside derivative suitable for the invention can in particular be obtained by the synthesis method described in document WO 02 / 051828.

[0162] Mention may in particular be made, by way of non-limiting illustration of the C-glycoside compounds which are particularly suitable for the invention, of the following compounds:

[0163] - C-[3-D-xylopyranoside-n-propan-2-one,

[0164] - C-a-D-xylopyranoside-n-propan-2-one,

[0165] - C-[3-D-xylopyranoside-2-hydroxypropane,

[0166] - C-a-D-xylopyranoside-2-hydroxypropane,

[0167] - l-(C-[3-D-fucopyranoside)propan-2-one,

[0168] - l-(C-a-D-fucopyranoside)propan-2-one,

[0169] - l-(C-[3-L-fucopyranoside)propan-2-one,

[0170] - l-(C-a-L-fucopyranoside)propan-2-one,

[0171] - l-(C-[3-D-fucopyranoside)-2-hydroxypropane,

[0172] - l-(C-a-D-fucopyranoside)-2-hydroxypropane,

[0173] - l-(C-[3-L-fucopyranoside)-2-hydroxypropane,

[0174] - l-(C-a-L-fucopyranoside)-2-hydroxypropane,

[0175] - l-(C-[3-D-glucopyranosyl)-2-hydroxypropane,

[0176] - l-(C-a-D-glucopyranosyl)-2-hydroxypropane,

[0177] - l-(C-[3-D-galactopyranosyl)-2-hydroxypropane,

[0178] - l-(C-a-D-galactopyranosyl)-2-hydroxypropane,

[0179] - l-(C-[3-D-fucofuranosyl)propan-2-one,

[0180] - l-(CaD-fucofuranosyl)propan-2-one,

[0181] - l-(C-[3-L-fucofuranosyl)propan-2-one,

[0182] - l-(CaL-fucofuranosyl)propan-2-one,

[0183] - CPD-maltopyranoside-n-propan-2-one,

[0184] - CaD-maltopyranoside-n-propan-2-one,

[0185] - C-[3-D-maltopyranoside-2-hydroxypropane,

[0186] - CaD-maltopyranoside-2-hydroxypropane, their isomers and their mixtures.

[0187] According to one embodiment, C-[3-D-xylopyranoside-2-hydroxypropane or CaD-xylopyranoside-2-hydroxypropane and better still C-[3-D-xylopyranoside-2-hydroxypropane can advantageously be used for the preparation of a composition according to the invention.

[0188] According to a specific embodiment, the C-glycoside compound may be C-[3-D-xylopyranoside-2-hydroxypropane (or hydroxypropyl tetrahydropyrantriol) provided as a solution containing 35% by weight of active material in propylene glycol.

[0189] 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

[0190] 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.

[0191] A person skilled in the art can select the amount of additional adjuvants or additives so as not to have a negative impact on the final use of the composition according to the present invention.

[0192] Preferably, the composition of the present invention comprises at least one water-soluble polymer with hydrophobic association.

[0193] As used herein, a water-soluble polymer with a hydrophobic association means any amphiphilic polymer having in its structure at least one fatty chain as hydrophobic end and at least one hydrophilic portion as backbone.

[0194] Preferably, the water-soluble polymer with hydrophobic association is chosen from polyether-polyurethanes with non-ionic association, crosslinked polyacrylate polymers and a combination thereof.

[0195] - Non-ionic associative polyether-polyurethanes:

[0196] 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.

[0197] 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 for the hydrocarbon chains to be pendant chains or chains at the end of a hydrophilic sequence. In particular, it is possible to envisage one or more pendant chains. In addition, the polymer may comprise a hydrocarbon chain at one end or at both ends of a hydrophilic sequence.

[0198] Polyether 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.

[0199] 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.

[0200] The polyether-polyurethanes containing a fatty chain may be triblock copolymers whose hydrophilic sequence is a polyoxyethylenated chain comprising from 50 to 1,000 oxyethylenated groups.

[0201] Polyether polyurethanes have a urethane bond between the hydrophilic sequences, hence the origin of the name.

[0202] By extension, those whose hydrophilic sequences are linked by other chemical bonds to the hydrophobic sequences are also included among the non-ionic polyether-polyurethanes comprising a hydrophobic chain.

[0203] As examples of non-ionic polyether-polyurethanes with a hydrophobic chain which can be used in the present invention, it is also possible to use Rheolate® 205 with a urea function sold by the company RHEOX or Rheolates® 208, 204 or 212, as well as Acrysol® 1840.

[0204] Mention may also be made of the product ELFACOS T210® containing a C12-C14 alkyl chain and the product ELFACOS T212® containing a C[8] alkyl chain from the company AKZO.

[0205] ROHM & HAAS's DW 1206B® product with a C2o alkyl chain and a urethane linkage, sold at 20% solids in water, can also be used.

[0206] It is also possible to use solutions or dispersions of these polymers, particularly in water or in a hydroalcoholic medium. Examples of such polymers include 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.

[0207] The polyether-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 to 389 (1993).

[0208] As polyether-polyurethanes described above, mention may be made of polyether-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 aromatic sequences.

[0209] It may be preferable for the polyether-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 pendant chains and chains at the end of a hydrophilic block.

[0210] According to a particular 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 moles of ethylene oxide, (ii) a polyoxyethylenated stearyl alcohol comprising 100 moles of ethylene oxide, and (iii) a diisocyanate will be used.

[0211] Such polyurethanes / polyethers are notably marketed by the company Elementis under the name Rheolate FX 1100® and Rheoluxe 8118, which is a polycondensate of polyethylene glycol 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-13 6 / Steareth-100 / HDI Copolymer).

[0212] 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, (ii) stearyl alcohol or decyl alcohol, and (iii) at least one diisocyanate will be used.

[0213] These polyurethanes / polyethers are marketed in particular by the company Rohm & Haas under the names Aculyn 46® and Aculyn 44®.

[0214] Aculyn 46® having 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).

[0215] 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).

[0216] As associative polyurethanes, it may be preferable to use a compound represented by the following formula (1):

[0217] R1-{(O-R2)k-OCONH-R3[-NHCOO-(R4-O)n-R5]h]m (1)

[0218] wherein R1 represents a hydrocarbon group, R2 and R4 independently represent alkylene groups having 2 to 4 carbon atoms, which alkylene groups may be the same as or different from each other, or a phenylethylene group, R3 represents a hydrocarbon group, which may optionally have a urethane linkage, R5 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.

[0219] 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'-[(O-R2)k-OH]m, at least one polyisocyanate which is represented by the formula R3-(NCO)h+i, and at least one polymonoalcohol which is represented by the formula HO-(R4-O)n-R5.

[0220] In these cases, R1 to R5 in the general formula (1) are determined by the compounds R'-[(O-R2)k-OH]m, R3-(NCO)h+i and HO-(R4-O)n-R5. The charge ratios between the three compounds are not particularly limited 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 selected from the NCO / OH range of 0.8:1 to 1.4:1.

[0221] The polyether polyol compound which is represented by the formula R'-[(O-R2)k-OH]m and which can be preferably used to obtain the associative thickener represented by the general formula (1) can be obtained by addition polymerization 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.

[0222] 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 di-pentaerythritol, sorbitol, mannitol and iditol; and octahydric alcohols, such as sucrose.

[0223] Similarly, R2 is determined by the alkylene oxide, styrene oxide, or the like, which is subjected to the addition. In particular, for reasons of availability and excellent effects, an alkylene oxide having 2 to 4 carbon atoms, or a styrene oxide is preferable.

[0224] The alkylene oxide, styrene oxide, or the like to be subjected to addition may be subjected to simple polymerization, or random polymerization, or block polymerization of at least two members. The procedure for the addition may be a conventional procedure. In addition, the degree of polymerization k may be selected 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. Furthermore, the ratio of the ethylene group occupying R2 should preferably be in the range of 50 to 100% by mass relative to the total amount of R2. In such cases, the associative thickener suitable for the purposes of the present invention is obtained.

[0225] Furthermore, the molecular weight of the polyether polyol compound which is represented by the formula R'-[(O-R2)k-OH]m should preferably be selected in the range of 500 to 100,000, and more preferably should be selected in the range of 1,000 to 50,000.

[0226] The polyisocyanate which is represented by the formula R3-(NCO)h+i 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 particularly limited as long 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.

[0227] 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.

[0228] 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 R3-(NCO) n+1, it is preferable to use the above-mentioned polyisocyanate having the urethane bond.

[0229] The polyether monoalcohol which is represented by the formula HO-(R4-O)n-R5 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 particularly limited to the extent that the polyether monoalcohol is a polyether of a straight-chain, branched-chain or secondary monohydric alcohol. The polyether monoalcohol can 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.

[0230] 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.

[0231] According to the present invention, it is preferable that the polyether-polyurethane is chosen from the steareth-100 / PEG-136 / HDI copolymer sold by the company Rheox under the name Rheolate FX 1100, the PEG-240 / HDI bis-decyltetradeceth-20 ether copolymer sold by the company Asahi Denka under the name Adekanol GT-700, and a combination thereof.

[0232] - Crosslinked polyacrylate polymers

[0233] The term "crosslinked polyacrylate polymer", as used herein, refers to a copolymer of acrylic acid, methacrylic acid or one of its esters, crosslinked with glycol dimethacrylate.

[0234] The following is a non-limiting list of crosslinked polyacrylate polymers, which may be used in the composition of the present invention.

[0235] The crosslinked polyacrylate-1 polymer is a copolymer of one or more simple esters of acrylic or methacrylic acid, C1-4 alkyl methacrylate di-C1-6 alkylamino, PEG / PPG-30 / 5 allyl ether, PEG 20-25 C10-30 alkyl ether methacrylate, C2-6 hydroxyalkyl methacrylate crosslinked with ethylene glycol dimethacrylate. This copolymer is commercially available as Carbopol Aqua CC Polymer brand from Lubrizol Advanced Materials, Inc. (Cleveland, Ohio).

[0236] The polyacrylate-2 crosslinked polymer is a copolymer of PEG / PPG-23 / 6 dimethicone citraconate, PEG-25 C10-30 alkyl methacrylate and one or more monomers of acrylic acid, methacrylic acid or a simple ester thereof, crosslinked with PEG-15 trimethylolpropane triacrylate. This copolymer is commercially available under the trademark Fixate Superhold Polymer from Lubrizol Advanced Materials, Inc. (Cleveland, Ohio).

[0237] Polyacrylate-3 crosslinked polymer is a copolymer of butyl acrylate, PEG-10 acrylate, PPG-6 acrylate and dimethylacrylamide, crosslinked with PEG-23 diacrylate. This copolymer is commercially available under the trademark Plascize L-64S from Goo Chemical Company, Ltd. (Kyoto, Japan).

[0238] 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 trademark Sepinov P500 from Seppic (Paris, France).

[0239] Polyacrylate-5 crosslinked polymer is commercially available under the trademark COSP23 from Miyoshi Kasei, Inc. (Urawa, Japan).

[0240] The crosslinked polyacrylate-6 polymer is a copolymer of ammonium acryloyldimethyltaurate, dimethylacrylamide, lauryl methacrylate and laureth-4 methacrylate, crosslinked with trimethylolpropane triacrylate. This copolymer is commercially available under the brand name Sepimax Zen from Seppic Affaires Réglementaires (Puteaux, France).

[0241] The polyacrylate-7 crosslinked polymer is a copolymer of PPG-6 phosphate methacrylate and one or more monomers of acrylic acid, methacrylic acid, or a simple ester thereof, crosslinked with PEG / PPG-25 / 29 dimethicone acrylate. This copolymer is commercially available under the trademark Y-17552 from Momentive Performance Materials (Friendly, W. Va.).

[0242] The crosslinked polyacrylate-8 polymer is a copolymer of t-butyl methacrylate, stearyl methacrylate, methoxy PEG-23 methacrylate and dimethylacrylamide, crosslinked with ethylene glycol dimethacrylate.

[0243] The crosslinked polyacrylate-9 polymer is a copolymer of t-butylaminoethyl methacrylate and carboxyethyl acrylate, crosslinked with a combination of pentaerythritol tetraacrylate and a hexafunctional acrylate formed by reacting pentaerythritol triacrylate with toluene diisocyanate.

[0244] Polyacrylate-10 crosslinked polymer is the crosslinked polymer prepared by polymerizing a mixture of trimethoxysilylpropyl methacrylate with trimethyloylpropane trime-thacrylate.

[0245] Polyacrylate-11 crosslinked polymer is a polymer of methacrylic acid, acryloyl dimethyltaurate and dimethylacrylamide, crosslinked with PPG-3 glyceryl triacrylate, and partially neutralized with ammonia. This copolymer is commercially available under the trademark Aristoflex Velvet from Clariant International Ltd. (Muttenz, Switzerland).

[0246] The crosslinked polyacrylate-12 polymer is a copolymer of t-butyl methacrylate, stearyl methacrylate, methoxy PEG-23 methacrylate and dimethylacrylamide, crosslinked with methylene bis-acrylamide.

[0247] Polyacrylate-14 crosslinked polymer is a copolymer of acrylic acid, lauryl methacrylate, cetyl methacrylate, stearyl methacrylate and phosphorylcholine glycol methacrylate, crosslinked by a pentaerythritol allyl ether. This copolymer is commercially available under the trademark Phosphomer ST610KC from KC1 Ltd. (Seoul, South Korea).

[0248] According to certain embodiments, the composition according to the present invention comprises a crosslinked polyacrylate polymer selected from polyacrylate-1 crosslinked polymer, polyacrylate-2 crosslinked polymer, polyacrylate-3 crosslinked polymer, polyacrylate-4 crosslinked polymer, polyacrylate-5 crosslinked polymer, polyacrylate-6 crosslinked polymer, polyacrylate-7 crosslinked polymer, polyacrylate-8 crosslinked polymer, polyacrylate-9 crosslinked polymer, polyacrylate-10 crosslinked polymer, polyacrylate-11 crosslinked polymer, polyacrylate-12 crosslinked polymer, polyacrylate-14 crosslinked polymer, and a combination thereof.

[0249] Preferably, the composition according to the present invention comprises one or more selected from polyacrylate-1 crosslinked polymer, polyacrylate-6 crosslinked polymer, polyacrylate-9 crosslinked polymer, and polyacrylate-11 crosslinked polymer.

[0250] More preferably, the composition according to the present invention comprises a water-soluble polymer with hydrophobic association chosen from crosslinked polyacrylate-6 polymer, steareth-100 / PEG-136 / HDI copolymer, PEG-240 / HDI bis-decyltetradeceth-20 ether copolymer and a combination thereof.

[0251] If 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.

[0252] 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:

[0253] (i) from 0.5% by weight to 5% by weight of ARACHIDYL ALCOHOL (and) BEHENYL ALCOHOL (and) ARACHIDYL GLUCOSIDE;

[0254] (ii) from 0.5% by weight to 5% by weight of POLYGLYCERYL-6 DISTEARATE (and) JOJOBA ESTERS (and) CETYL ALCOHOL (and) PO-LYGLYCERYL-3 BEESWAX;

[0255] (iii) from 0.1% by weight to 2% by weight of a compound selected from 2-oleamido-1,3-octadecanediol and ceramide NP;

[0256] (iv) from 1% by weight to 5% by weight of hydroxypropyl tetrahydropyrantriol; and

[0257] (v) from 0.3% by weight to 3% by weight of a water-soluble polymer with hy drophobe selected from polyacrylate-6 crosslinked polymer, steareth-100 / PEG-136 / HDI copolymer, PEG-240 / HDI copolymer, bis-decyltetradeceth-20 ether, and a combination thereof. Dosage form and process

[0258] The composition of the present invention is in the form of an oil-in-water emulsion.

[0259] The composition according to the present invention has a lamellar structure.

[0260] The term "lamellar structure" means 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 exhibits 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 has been observed, it means that the lamellar structure is formed.

[0261] The composition of the present invention can be used for the care of keratinous materials.

[0262] According to the second aspect, the present invention provides a non-therapeutic method of caring for keratinous materials, comprising applying the composition according to the first aspect of the present invention to the keratinous materials.

[0263] The following examples serve to illustrate the present invention without, however, being of a limiting nature. EXAMPLES

[0264] The main raw materials used, their trade names and their suppliers are listed in Table 1.

[0265] [Tables 1] Nom INCI Nom commercial Fournisseur 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 DILAURAMIDO- GLUTAMIDE LYSINE PELLICER LB-30G ASAHI KASEI PHENOXYETHANOL HISOLVE EPH TOHO CHEMICALS HYDROXYPROPYL TETRAHY- DROPYRANTRIOL 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) POLY-GLYCERYL-3 BEESWAX EMULIUM MELLIFERA MB GATTEFOSSE 2-OLEAMIDO-1,3-OCTADECANE DIOL 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 SOUDE CAUSTIQUE 50 % DOW

[0266] Exemples d’invention 1 et 2 et exemples comparatifs 1 et 2

[0267] The compositions of the invention examples (El.) 1 and 2 and of the 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 total weight of the composition containing it.

[0268] [Tables2] Components El. 1 EL 2 EC. 1 EC. 2 HYDROXYPROPYL TETRAHY- DROPYRANTRIOL 3.15 3.15 3.15 3.15 PEG-240 / HDI BIS-DECYLTETRADECETH-20 ETHER COPOLYMER 2 2 2 2 POLY-ACRYLATE-6 CROSSPOLYMER 0.2 0.2 0.2 0.2 ARACHIDYL ALCOHOL (and) BEHENYL ALCOHOL (and) ARACHIDYL GLUCOSIDE » 2 2 - 2 POLY-GLYCERYL-6 DISTEARATE (and) JOJOBA ESTERS (and) CETYL ALCOHOL (and) POLY-GLYCERYL-3 BEESWAX 2 2 2 GLYCERYL STEARATE (and) STEARATE PEG-100 - - 2 - 2-OLEAMIDO-1,3-OCTADECANE DIOL 1 - - - CERAMIDE NP - 1 - - ALKANE CiSi9 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 DILAURAMIDOGLUTAMIDE SODIUM LYSINE 0.35 0.35 0.35 0.35 PHENOXYETHANOL 0.3 0.3 0.3 0.3 Water Ce 100 Ce 100 Ce 100 Ce 100

[0269] 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.

[0270] POLYGLYCERYL-6 DISTEARATE (and) JOJOBA ESTERS (and) CETYL ALCOHOL (and) POLYGLYCERYL-3 BEESWAX: comprising 64% by weight POLYGLYCERYL-6 DISTEARATE, 19% by weight JOJOBA ESTERS, 8.5% by weight CETYL ALCOHOL and 8.5% by weight POLYGLYCERYL-3 BEESWAX. Preparation process:

[0271] The compositions listed above were prepared as follows, taking as an example the composition of Invention Example 1:

[0272] 1). Mix the ingredients for an aqueous phase (glycerin, dilauramido- sodium glutamide lysine, phenoxyethanol and water) with a homogenizer and heat to 70°C.

[0273] 2). Mix ARACHIDYL ALCOHOL (and) BEHENYL ALCOHOL (and) ARACHIDYL GLUCOSIDE, POLYGLYCERYL-6 DISTEARATE (and) JOJOBA ESTERS (and) CETYL ALCOHOL (and) POLY-GLYCERYL-3 BEESWAX, 2-oleamido-l,3-octadecanediol C15-19 alkane, hexyldecanol with a homogenizer to obtain a mixture and heat to 70 °C.

[0274] 3). Introduce the mixture into the aqueous phase and maintain homogenization at 60°C for 10 min to obtain an O / W emulsion.

[0275] 4). Add the polymers (PEG-240 / HDI BIS-ETHER COPOLYMER) DECYLTETRADECETH-20, and POLYACRYLATE-6 CROSSLINKED POLYMER) into the emulsion and homogenize for 10 min.

[0276] 5). Transfer the emulsion into a disperser and cool the emulsion to room temperature room temperature, maintain stirring and add the hydroxypropyl tetrahydropyrantriol.

[0277] 6). Adjust the pH value with sodium hydroxide to obtain the com position. Assessment

[0278] 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

[0279] The possible formation of a lamellar structure was evaluated as follows.

[0280] The compositions were observed using a Leica DLMB microscope under 90° cross-polarized light, and microscopic photographs were taken. If optical effects characteristic of the lamellar structure were observed, this means that the lamellar structure was formed.

[0281] [Fig.l] shows a photograph of the composition of Invention Example 1 (ELI) taken with a polarized light microscope.

[0282] [Fig.2] shows a photograph of the composition of Invention Example 2 (EI.2) taken with a polarized light microscope. Skin finish

[0283] 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.

[0284] The results of the lamellar structure of each composition prepared above and the skin finish delivered are shown in Table 3.

[0285] [Tables3] Point EL 1 EL 2 EC. 1 EC. 2 lamellar structure YES YES YES YES Skin finish 4 4 2 3

[0286] NA: not observed. Transepidermal water loss (TEWL)

[0287] 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.

[0288] 18 pL (2 mg / cm2) of each tested sample was transferred and spread gently and evenly over each 3*3 cm2 test area. Transepidermal water loss (TEWL) obtained on an untreated area was used as a blank control.

[0289] A lower TEWL indicates better skin barrier function.

[0290] The results are summarized in Table 4.

[0291] [Tables4] Properties ELI El. 2 EC. 1 EC. 2 Commercial product Blank control TEWL (8h, %) -45.39 -38.50 -31.75 -32.20 -27.63 -0.45

[0292] It can be seen that the compositions of inventive examples 1 and 2 provide a better skin barrier function compared to the compositions of comparative examples 1 and 2 and the commercial product.

Claims

Claims

1. 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 ALCOHOL (and) BEHENYL ALCOHOL (and) ARACHIDYL GLUCOSIDE; (ii) from 0.5% by weight to 5% by weight of POLY-GLYCERYL-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 selected 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 a hydrophobic association selected from polyacrylate-6 crosslinked polymer, steareth-100 / PEG-136 / HDI copolymer, PEG-240 / HDI copolymer, bis-decyltetradeceth-20 ether, and a combination thereof.

2. Non-therapeutic method for caring for keratinous materials, comprising applying the composition according to claim 1 to the keratinous materials.