CN118973534A - Composition for caring for keratin materials - Google Patents

Abstract

To a composition in the form of an oil-in-water emulsion for caring for keratin materials, comprising: (i) At least one nonionic surfactant selected from the group consisting of sugar ethers of C ₈-C₂₂ 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. Also relates to a non-therapeutic method for caring for keratin materials, comprising the application of said composition to the skin.

Description

Composition for caring for keratin materials

Technical Field

The present invention relates to cosmetic compositions. In particular, the present invention relates to compositions for the care of keratin materials. The present invention also relates to non-therapeutic methods for the care of keratin materials.

Background Art

Skin acts as a natural barrier between the internal environment and the external environment, and therefore plays an important role in vital biological functions (such as defense against mechanical and chemical damage, microorganisms and ultraviolet damage). However, the health and appearance of the skin can deteriorate due to environmental factors, genetic composition, nutrition and sun exposure. With aging, even if the number of cell layers remains unchanged, the outer skin layer (epidermis) also thins. However, the number of pigment cells (melanocytes) decreases. Therefore, the skin looks pale and translucent. Large pigment spots (age spots, liver spots or freckles) may appear in the sun-exposed area. Changes in connective tissue reduce the strength and elasticity of the skin. This is called elastosis. It is more obvious in the sun-exposed area (solar elastosis). Elastosis produces a leathery, weather-beaten appearance shared by farmers, sailors and other people who spend a lot of time outdoors. Dehydration increases the risk of skin damage. Poor nutrition can also have a negative impact on the skin, causing dryness, rashes and edema.

Ceramides are a group of natural waxy fatty substances in the skin that are made up of sphingosine and lipids (fatty acids) bonded together. Ceramides make up about 50% of all skin lipids and are produced in the lower living cells of the epidermis. As cells mature and move to the surface, ceramides are released into the topmost layer (the stratum corneum). In the stratum corneum, ceramides bind to cholesterol (another important lipid found in the skin) and fatty acids to form an orderly, tightly packed, layered sheet arrangement between dead cells. Ceramides and cholesterol prevent water loss to keep the skin young and supple, and support the skin's matrix, keeping it firm. Young individuals produce ample ceramides and cholesterol to keep their skin healthy. However, with aging, the production of ceramides and cholesterol declines, and the skin begins to appear saggy and wrinkled.

To achieve stabilization and repair efficacy, skin barrier function enhancement is a necessary parameter, which means that transepidermal water loss (TEWL) should be a good attribute to characterize barrier function. However, ordinary products with excellent TEWL effect usually provide a greasy feel.

Therefore, there is a need to formulate compositions for caring for the skin that can enhance the skin barrier function without a greasy feel.

SUMMARY OF THE INVENTION

The inventors have now discovered that it is possible to formulate a composition for caring for the skin which enhances the skin barrier function without a greasy feel.

Thus, according to a first aspect, the present invention provides a composition in the form of an oil-in-water emulsion for caring for keratin materials comprising:

(i) at least one nonionic surfactant selected 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 polyglycerol diester; and

(iii) at least one ceramide-type compound.

The composition of the invention is in the form of an oil-in-water emulsion. Thus, the 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 structure or liquid crystal.

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

According to a second aspect, the present invention provides a non-therapeutic method for caring for keratin materials, which comprises applying to the keratin material a composition according to the first aspect of the invention.

Other advantages of the invention will emerge more clearly on reading the following description and examples.

BRIEF DESCRIPTION OF THE DRAWINGS

By way of example only, implementations of the present invention will now be described with reference to the accompanying drawings, in which:

FIG. 1 shows a photograph of the composition of Inventive Example 1 (IE.1) taken using a polarized light microscope.

FIG. 2 shows a photograph of the composition of Inventive Example 2 (IE.2) taken using a polarized light microscope.

Detailed description of the invention

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 invention belongs. When the definition of a term in this specification conflicts with the meaning commonly understood by those skilled in the art to which the invention belongs, the definition described herein shall apply.

In the following and unless otherwise indicated, the limits of a range of values are included in the range, especially in the expressions “between… and…” and “ranging from… to…”.

In addition, the expression "at least one" used in the present specification is equivalent to the expression "one or more".

Throughout this application, the term "comprising/including" should be interpreted as covering all specifically mentioned features as well as optional, additional, unspecified features. As used herein, the use of the term "comprising/including" also discloses embodiments in which there are no features other than the specifically mentioned features (i.e., "consisting of ...").

Unless otherwise indicated, all numerical values expressing quantities of ingredients and the like used in the specification and claims are to be understood as modified by the term “about.” Accordingly, unless indicated to the contrary, the numerical values and parameters described herein are approximations that can vary as necessary depending on the desired purpose.

For the purposes of the present invention, the term "keratin material" is intended to cover human skin, mucous membranes (eg lips). The facial skin is most particularly contemplated according to the present invention.

Unless otherwise specified, all percentages in the present invention are by weight.

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

(i) at least one nonionic surfactant selected 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 polyglycerol diester; and

(iii) at least one ceramide-type compound.

Nonionic surfactant selected from sugar ethers of _C8 - _C22 fatty alcohols

According to a first aspect, the present invention comprises at least one nonionic surfactant selected from sugar ethers of _C8 - _C22 fatty alcohols.

Sugar ethers that may be mentioned in particular are alkyl polyglycosides (APGs). The alkyl polyglycosides may be used alone or as a mixture of two or more alkyl polyglycosides. The alkyl polyglycosides generally have the following formula (I):

R(O)(G) _n (I)

in:

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

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

Alkyl polyglycosides useful according to the invention include, for example:

- decyl glucoside, 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 NS10 by the company SEPPIC;

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

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

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

- cetearyl glucoside, optionally as a mixture with cetearyl alcohol, such as sold 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, APG can be used as a mixture with a fatty alcohol, in particular a fatty alcohol having 8-30 carbon atoms, such as 10-20 carbon atoms. Preferably, for such a mixture, the alkyl polyglycoside and the fatty alcohol have similar carbon atoms, such as a difference of less than 5, especially less than 3 or less than 2. More preferably, the alkyl polyglycoside and the fatty alcohol used in the mixture have the same carbon atoms. For example, the alkyl polyglycoside and the fatty alcohol in the mixture may have the same alkyl moiety.

Alkyl polyglycoside/fatty alcohol mixtures are known in the art, see for example WO 9847610 and WO9513863.

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

-Myristyl alcohol/myristyl glucoside: Montanov 14;

- Isostearyl alcohol/isostearyl glucoside: Montanov WO 18;

- Cetearyl Alcohol/Cetearyl Glucoside: Montanov 68;

- Cetearyl Alcohol/Coco-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/Coco-Glucoside: Montanov S.

Other useful APGs may include, for example, decyl glucoside and lauryl glucoside, such as are sold under the respective names Plantaren 2000 and Plantaren 1200 by the company Henkel. In addition, mixtures of cetearyl glucoside and cetearyl alcohol are sold, in addition to Montanov 68, for example, under the names Tegocare CG90 by the company Goldschmidt and Emulgade KE3302 by the company Henkel.

Advantageously, the nonionic surfactant selected from sugar ethers of _C8 - _C22 fatty alcohols is present in the composition of the invention in an amount ranging from 0.1 wt.% to 10 wt.%, preferably 0.5 wt.% to 5 wt.%, more preferably 0.5 wt.% to 5 wt.%, relative to the total weight of the composition of the invention.

Ester type nonionic surfactant

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

Preferably, the ester type nonionic surfactant comprises:

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

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

in:

R1 and R2 each represent a C18-C44 fatty chain, at least one of R1 or R2 is monounsaturated; and

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

R3-C(O)-(O-CH2-CH(OH)-CH2)n-O-C(O)-R4(III)

in:

R3 and R4 represent a linear or branched saturated C18-C44 fatty chain, respectively.

Specifically, in formula (II), R1 and R2 each represent a C18-C40 fatty chain, more preferably a C18-C30 fatty chain. At least one of R1 or R2 is monounsaturated.

More specifically, in formula (II), the R1-C(O)-group corresponds to the carbon chain of a fatty acid. The chain may be straight or monounsaturated and contain at least 18 carbon atoms. As for unsaturated acids, oleic acid (C18:1), gadoleic acid (C20:1), erucic acid (C22:1), up to hexacosenoic acid (C26:1) may be mentioned. The R1-C(O)-group may also consist of branched and saturated acids (also called Guerbet acids) of at least 18 carbon atoms. The R2-O-group may consist of monounsaturated straight-chain fatty alcohols containing at least 18 carbon atoms. Thus, octadecenol, eicosenol, docosenol and hexacosenol may be mentioned. The carbon chain of the alcohol may also be branched and saturated and contain 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 fatty chains of various lengths in its structure. More preferably, such monounsaturated esters are liquid at ambient temperature.

Preferred monounsaturated esters that may be mentioned are for example the products commonly known as jojoba oil (or jojoba esters), the liquid properties of which are due to the presence of monounsaturated chains. This oil comprises in particular C18:1 (preferably a minority), C20:1 and C22:1 (preferably a majority, wherein C20:1>C22:1) unsaturated fatty acid esters, and C20:1, C22:1 and C24:1 unsaturated fatty alcohols.

Preferably, in formula (III), the R3—C(O)—group corresponds to the carbon chain of a C18-C44 fatty acid, which is usually linear and saturated, preferably corresponds to a linear and saturated C20-C34 fatty acid. Thus, this includes eicosanoic acid (or arachidic acid) (C20), docosanoic acid (or behenic acid) (C22), tetracosanoic acid (or lignoceric acid) (C24), hexacosanoic acid (or cerotic acid) (C26). The R4 group corresponds to the hydrocarbon chain of an alcohol, which is usually saturated and linear and has a C18-C44 chain, preferably a C20-C34 chain. n is an integer between 2 and 6.

According to the invention, the polyglycerol diesters are obtained by esterification of solid waxes in the presence of at least one polyol.

Solid waxes suitable for obtaining polyglycerol diesters have a melting point between 50° C. and 90° C. They correspond to mixtures essentially comprising monoesters of the formula R ¹ —C(O)—O—R ² , wherein the R ¹ —C(O)— group corresponds to the carbon chain of a 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. Thus, this includes eicosanoic acid (or arachidic acid) (C20), docosanoic acid (or behenic acid) (C22), lignoceric acid (or lignoceric acid) (C24), hexacosanoic acid (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 acid or hydroxystearic acid. This is the case, for example, with beeswax. The R ² group corresponds to the hydrocarbon chain of an alcohol, said alcohol being generally saturated and linear and having a number of carbon atoms of at least 18, and in particular 20, and preferably up to 44 and preferably 34. Preferably, the alcohol is eicosanol, docosanol or tetracosanol.Beeswax, carnauba wax, candelilla wax, rice bran wax, sunflower wax, carnauba wax, shellac wax and sugar cane wax are examples of natural solid waxes.

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

Preferably, the polyol used for esterification is selected from ethylene glycol, diethylene glycol, triethylene glycol, 2-methylpropanediol, propylene glycol, butylene glycol, neopentyl glycol, hexylene glycol, octanediol, polyethylene glycol, polypropylene glycol, trimethylolpropane, sorbitol, erythritol, pentaerythritol, dipentaerythritol, glycerol, diglycerol and polyglycerol (i.e., polymer of glycerol units). More preferably, the polyol is polyglycerol, and its average degree of polymerization is between 2 and 6, preferably 3. Preferably, the polyol is polyglycerol-3.

Nonionic ester surfactants also contain the acid part of solid wax. Waxes have a complex composition. They have the common feature 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 at least one solid wax and at least one monounsaturated ester of formula (II) together in the presence of at least one polyol and optionally at least one catalyst. In such cases, an ester exchange reaction occurs between the various chemical entities that produce the wax derivative.

Preferred catalysts are hydroxides or alkali metal alkoxides or alkaline earth metal alkoxides, calcium hydroxide, potassium carbonate or sodium carbonate, or catalysts based on tin or titanium.

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

In a preferred embodiment, the wax derivative is obtained by reacting jojoba oil (also known as jojoba wax), beeswax, and polyglycerol (eg, 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 ester/polyol mass ratio of formula (II) and formula (III) preferably varies between 1/99 and 99/1 (advantageously between 95/5 and 50/50). Preferably, the proportion of esterified polyols is between 0.5% and 50% by weight of the mixture, the proportion of esterified fatty acids is between 20% and 60% by weight of the mixture, and the proportion of esterified fatty alcohols is between 20% and 60% by weight of the mixture.

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

Typically, the _C14 - _C22 fatty acid may be selected from myristic acid, stearic acid, isostearic acid, palmitic acid, oleic acid, behenic acid, erucic acid and arachidic acid, and mixtures thereof.

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

Preferably, the diester is a diester of distearic acid and hexaglycerol. Preferably, it is polyglyceryl-6 distearate.

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

As examples of fatty alcohols that can be used, mention may be made of linear or branched fatty alcohols of synthetic origin or alternatively of natural origin, for example alcohols derived from vegetable material (coconut, palm kernel, palm, etc.) or animal material (tallow, etc.). Preference is given to using fatty alcohols containing 20 to 26 carbon atoms, preferably 10 to 24 carbon atoms and more preferably 12 to 22 carbon atoms.

As particular examples of fatty alcohols that can be used in the context of the present invention, mention may especially be made of lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, palmityl alcohol, oleyl alcohol, cetearyl alcohol (a 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 invention to use a mixture of polyglyceryl-6 distearate and polyglyceryl-3 beeswax with cetyl alcohol and jojoba wax. Among particularly preferred mixtures, mention may be made of the mixture sold by the company Gattefosse under the name JOJOBA wax, cetyl alcohol, polyglyceryl-6 distearate and polyglyceryl-3 beeswax. Product sold by Mellifera (INCI name: Polyglyceryl-6 Distearate (and) Jojoba Esters (and) Polyglyceryl-3 Beeswax (and) Cetyl Alcohol). The mixture comprises 5-30% by weight of jojoba wax; 3-15% by weight of cetyl alcohol; at least 50% by weight of polyglyceryl-6 distearate; and 3-15% by weight of polyglyceryl-3 beeswax, relative to the total weight of the mixture.

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

Ceramide-type compounds

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

According to the invention, the term "ceramide-type compound" is understood to mean a natural or synthetic ceramide and/or glycoceramide and/or ceramide-like compound and/or neoceramide.

Ceramide-type compounds are disclosed, for example, in patent applications DE 4424530, DE 4424533, DE 4402929, DE4420736, 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 that can be used according to the invention preferably correspond to the general formula (I):

in:

-R ₁ means:

- a saturated or unsaturated and linear or branched C ₁ -C ₅₀ hydrocarbon group, preferably a C ₅ -C ₅₀ hydrocarbon group, which may be substituted by one or more hydroxyl groups optionally esterified with an acid R ₇ COOH, R ₇ is an optionally monohydroxylated or polyhydroxylated, saturated or unsaturated and linear or branched C ₁ -C ₃₅ hydrocarbon group, one or more hydroxyl groups of the R ₇ group may be esterified with an optionally monohydroxylated or polyhydroxylated, saturated or unsaturated and linear or branched C ₁ -C ₃₅ fatty acid;

- or R"-(NR-CO)-R' group, wherein R represents a hydrogen atom, or a monohydroxylated or polyhydroxylated C ₁ -C ₂₀ hydrocarbon group, preferably a monohydroxylated C ₁ -C ₂₀ hydrocarbon group, R' and R" are hydrocarbon groups, the sum of their carbon atoms being between 9 and 30, and R' is a divalent group;

- or R ₈ -O-CO-(CH ₂ ) _p group, wherein R ₈ represents a C ₁ -C ₂₀ hydrocarbon group, and p is an integer ranging from 1 to 12;

- _R2 is selected from a hydrogen atom; a glycosyl group, in particular a (glycosyl) _n , (galactosyl) _m or sulfogalactosyl group, a sulfate residue or a phosphate residue, a phosphoethylamine group and a phosphoethylammonium group, wherein n is an integer varying from 1 to 4, and m is an integer varying from 1 to 8;

- R ₃ represents a hydrogen atom, or a hydroxylated or non-hydroxylated and saturated or unsaturated C ₁ -C ₃₃ hydrocarbon group, one or more hydroxyl groups may be esterified by an inorganic acid or acid R ₇ COOH, R ₇ has the same meaning as above, and one or more hydroxyl groups may be etherified by (glycosyl) _n , (galactosyl) _m , sulfogalactosyl, phosphoethylamine group or phosphoethylammonium group, and R ₃ may also be substituted by one or more C ₁ -C ₁₄ alkyl groups;

Preferably, R ₃ represents a C ₁₅ -C ₂₆ α-hydroxyalkyl group, the hydroxy group being optionally esterified with a C ₁₆ -C ₃₀ α-hydroxy acid;

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

- R ₅ represents a hydrogen atom or an optionally monohydroxylated or polyhydroxylated, saturated or unsaturated and linear or branched C ₁ -C ₃₀ hydrocarbon group, one or more of which may be etherified by a (glycosyl) _n , (galactosyl) _m , sulfogalactosyl, phosphoethylamine or phosphoethylammonium group;

The proviso is 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 group.

Among the compounds of formula (I), preference is given to ceramides and/or glycoceramides having the structure described by Downing in Journal of Lipid Research (Vol. 35, 2060-2068, 1994) or those disclosed in French patent application FR-2 673 179, the teaching of which is included herein by reference.

More particularly preferred ceramide-type compounds according to the present invention are compounds of formula (I), wherein R ₁ represents an optionally hydroxylated and saturated or unsaturated hydrocarbon group derived from a C ₁₄ -C ₂₂ fatty acid; R ₂ represents a hydrogen atom; and R ₃ represents an optionally hydroxylated and linear C ₁₁ -C ₁₇ group (and preferably a C ₁₃ -C ₁₅ group). R ₃ preferably represents an α-hydroxycetyl group, and R ₂ , R ₄ and R ₅ represent a hydrogen atom.

Such compounds are for example:

-2-N-linoleamidooctadecane-1,3-diol,

-2-N-oleoylaminooctadecane-1,3-diol (N-oleoyl dihydrosphingosine),

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

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

-2-N-Behenamidooctadecane-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 a mixture of these compounds.

Certain mixtures may also be used, for example mixtures of ceramide 2 and ceramide 5 according to the Downing classification.

Also useful are compounds of formula (I) wherein _R1 represents a saturated or unsaturated hydrocarbon group derived from a _C12 - _C22 fatty acid; _R2 represents a galactosyl group or a sulfogalactosyl group; and _R3 represents a saturated or unsaturated _C12 - _C22 hydrocarbon group, and preferably a -CH=CH-( _CH2 ) ₁₂ - _CH3 group.

By way of example, mention may be made of the product consisting 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.

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

N-docosapentaenoyl-N-methyl-D-glucamine disclosed in patent application WO 94/24097 may also be used.

Most preferably, the ceramide may be chosen from 2-oleamido-1,3-octadecanediol (CTFA name thereof), for example sold as MEXANYL GZ by Chimex; and ceramide NP (CTFA name N-stearoylphytosphingosine), for example sold as CERAMIDE III by EVONIK GOLDSCHMIDT.

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

Water Phase

As oil-in-water emulsions, the cosmetic compositions of the present invention comprise a continuous aqueous phase.

The aqueous phase comprises water.

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

Oil phase

As oil-in-water emulsions, the compositions according to the invention comprise at least one dispersed oily phase.

The fatty phase preferably comprises at least one oil.

Oils can be volatile or non-volatile.

The term "oil" means a water-immiscible non-aqueous compound that is liquid at room temperature (25° C.) and atmospheric pressure (760 mmHg). The term "non-volatile oil" means an oil that can remain on a keratin material for at least several hours at room temperature and atmospheric pressure, and in particular has a vapor pressure of less than 10 ^-3 mmHg (0.13 Pa). Non-volatile oils may 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/cm ² .

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

The oil may be selected from hydrocarbonized oils, silicone oils or fluorinated oils.

The term "hydrocarbon-based oil" means an oil that is essentially formed or even consists of carbon atoms and hydrogen atoms and optionally oxygen atoms and nitrogen atoms, and does not contain silicon heteroatoms and fluorine heteroatoms. Such oils may contain alcohol groups, ester groups, ether groups, carboxylic acid groups, amine groups and/or amide groups.

The term "silicone oil" denotes an oil containing at least one silicon atom, in particular containing Si-O groups.

The term "fluorinated oil" means an oil containing at least one fluorine atom.

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

Additional cosmetic active ingredients

In addition to the ceramide-type compounds, the compositions according to the invention may also comprise further cosmetically active ingredients.

As examples of cosmetic active ingredients, 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 (especially esters) of said vitamins and mixtures thereof; urea; caffeine; salicylic acid and its derivatives; alpha-hydroxy acids, such as lactic acid or glycolic acid, and their derivatives; sunscreens; extracts from algae, fungi, plants, yeasts and bacteria; enzymes; agents acting on the microcirculation, etc.

A person skilled in the art can easily adjust the amount of additional cosmetic active ingredients based on the end use of the composition according to the invention.

Preferably, the composition according to the invention comprises a cosmetically active compound selected from C-glycosides of formula (V):

in:

-R represents a saturated C ₁ -C ₁₀ (especially C ₁ -C ₄ ) alkyl group, which may be optionally substituted by at least one group selected from OH, COOH or COOR" ₂ , wherein R" ₂ is a saturated C ₁ -C ₄ alkyl group,

-S represents a mono- or polysaccharide containing up to 20 saccharide units, in particular up to 6 saccharide units, in the pyranose and/or furanose form and of the L and/or D series, which may be substituted by hydroxyl groups which must be free and optionally one or more optionally protected amine functions, and

-X represents a group selected from the group consisting of -CO-, -CH(OH)-, -CH(NH ₂ )-, -CH(NHCH ₂ CH ₂ CH ₂ OH)-, -CH(NHPh)- and -CH(CH ₃ )- groups, and in particular a -CO-, -CH(OH)- or -CH(NH ₂ )- group, and more particularly a -CH(OH)- group,

The S- _CH2 -X bond represents a bond of C-anomer isomeric nature, which can be α or β,

Also included are physiologically acceptable salts thereof, solvates thereof (eg hydrates), and optical isomers and geometric isomers thereof.

The C-glycosides of formula (V) used in the implementation of the invention are especially those in which R represents a saturated linear C ₁ -C ₆ (especially C ₁ -C ₄ , preferably C ₁ -C ₂ ) alkyl group, and more preferably a methyl group.

Among the alkyl radicals suitable for carrying out the invention, mention may especially be made of methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, isobutyl, sec-butyl, pentyl, n-hexyl, cyclopropyl, cyclopentyl or cyclohexyl.

According to one embodiment of the invention, C-glycoside compounds corresponding to formula (V) can be used, in which S can represent a monosaccharide or polysaccharide containing up to 6 sugar units, which are in the pyranose and/or furanose form and are of the L and/or D series, said monosaccharide or polysaccharide exhibiting at least one hydroxyl function which must be free and/or optionally one or more amine functions which must be protected, X and R otherwise retain all the definitions given above.

Advantageously, the 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, D-galacturonic acid, D-iduronic acid, N-acetyl-D-glucosamine or N-acetyl-D-galactosamine, and advantageously represents D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, and in particular D-xylose.

More particularly, the polysaccharide of the invention comprising up to 6 saccharide units may be chosen from D-maltose, D-lactose, D-cellobiose, D-maltotriose; a disaccharide combining a uronic acid selected from D-iduronic acid or D-glucuronic acid and a hexosamine selected 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-β-xylobiose, xylotriose, xylotetrose, xylopentaose and xylohexose, and in particular xylobiose, which is composed of two xylose molecules linked via a 1-4 bond.

More particularly, S may represent a monosaccharide selected from the group consisting of D-glucose, D-xylose, L-fucose, D-galactose or D-maltose, and especially D-xylose.

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

-R represents unsubstituted straight-chain C ₁ -C ₄ (especially C ₁ -C ₂ ) alkyl, especially methyl;

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

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

The acceptable salts of the compounds described in the present invention include conventional non-toxic salts of the compounds, such as those formed by organic or inorganic acids. By way of example, salts of inorganic acids (e.g., sulfuric acid, hydrochloric acid) may be mentioned. Salts of organic acids that may contain one or more carboxylic acid groups, sulfonic acid groups, or phosphonic acid groups may also be mentioned. Propionic acid, acetic acid, terephthalic acid, citric acid, and tartaric acid may be mentioned in particular.

When the compound of formula (V) contains acid groups, neutralization of the acid groups 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 an organic base, such as a primary, secondary or tertiary alkylamine, such as triethylamine or butylamine. The primary, secondary or tertiary alkylamine may contain one or more nitrogen atoms and/or oxygen atoms and may therefore contain, for example, one or more alcohol functions; mention may be made especially of 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 of the compounds described in the present invention include conventional solvates, such as those formed during the final stages of the preparation of the compounds due to the presence of solvents. By way of example, solvates produced by the presence of water or straight-chain or branched alcohols (such as ethanol or isopropanol) may be mentioned.

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

The C-glycoside derivatives suitable for the present invention can be obtained in particular by the synthesis method described in document WO 02/051828.

By way of non-limiting illustration of C-glycoside compounds particularly suitable for the present invention, mention may especially be made of the following compounds:

-C-β-D-xylopyranosyl-n-propan-2-one,

-C-α-D-xylopyranosyl-n-propan-2-one,

-C-β-D-xylopyranosyl-2-hydroxypropane,

-C-α-D-xylopyranosyl-2-hydroxypropane,

-1-(C-β-D-fucopyranosyl)propan-2-one,

-1-(C-α-D-fucopyranosyl)propan-2-one,

-1-(C-β-L-fucopyranosyl)propan-2-one,

-1-(C-α-L-fucopyranosyl)propan-2-one,

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

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

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

-1-(C-α-L-fucopyranosyl)-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-maltopyranosyl-n-propan-2-one,

-C-α-D-maltopyranosyl-n-propan-2-one,

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

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

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

According to a particular embodiment, the C-glycoside compound may be C-β-D-xylopyranosyl-2-hydroxypropane (or hydroxypropyltetrahydropyrantriol) provided as a solution containing 35% by weight of active material in propylene glycol.

If present, the cosmetically active compound selected from C-glycosides of formula (V) is advantageously present in the composition in an amount ranging from 0.1 wt.% to 10 wt.%, preferably from 0.5 wt.% to 7 wt.%, preferably from 1 wt.% to 5 wt.%, relative to the total weight of the composition.

Other adjuvants or additives

The compositions of the present invention may contain conventional cosmetic adjuvants or additives, such as fragrances, chelating agents, preservatives and bactericides, thickeners, pH adjusters, fillers and mixtures thereof.

A person skilled in the art can select the amount of further adjuvants or additives so as not to adversely affect the end use of the composition according to the invention.

Preferably, the compositions according to the invention comprise at least one hydrophobically associating water-soluble polymer.

As used herein, a hydrophobically associating water-soluble polymer refers to any amphiphilic polymer having at least one fatty chain as a hydrophobic end and at least one hydrophilic part as a blockbone in its structure.

Preferably, the hydrophobically associating water-soluble polymer is selected from the group consisting of nonionic associative polyether-polyurethanes, polyacrylate cross-linked polymers, and combinations thereof.

Nonionic associative polyether-polyurethane:

The polymer may contain in its chain both hydrophilic sequences, which are most often of a polyoxyethylenated nature, and hydrophobic sequences which may be solely aliphatic and/or cycloaliphatic and/or aromatic bonds.

Preferably, these polyether-polyurethanes contain at least two lipophilic hydrocarbon chains having 6 to 30 (preferably 8 to 30) carbon atoms separated by a hydrophilic sequence. The hydrocarbon chain may be a side chain or a chain at the end of the hydrophilic sequence. In particular, one or more side chains are conceivable. In addition, the polymer may contain a hydrocarbon chain at one or both ends of the hydrophilic sequence.

The polyether-polyurethanes may be multiblock, especially in triblock form. The hydrophobic sequences may be at each end of the chain (e.g. triblock copolymers with a hydrophilic core sequence) or distributed at the ends and in the chain (e.g. multiblock copolymers). These same polymers may also be in the form of grafted units or may be in star shape.

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

The polyether-polyurethane containing aliphatic chains may be a triblock copolymer, the hydrophilic sequence of which is a polyoxyethylenated chain containing 50-1000 oxyethylenated groups.

Polyether-polyurethanes contain urethane bonds between the hydrophilic sequences, hence their name.

By extension, the nonionic polyether-polyurethanes containing hydrophobic chains also include those whose hydrophilic sequences are linked to hydrophobic sequences by other chemical bonds.

By way of example of nonionic polyether-polyurethanes containing hydrophobic chains which can be used in the present invention, urea-functional polyethers sold by the company RHEOX can also be used. 205, or 208, 204 or 212, and 1840.

Mention may also be made of the product ELFACOS from AKZO containing C ₁₂ -C ₁₄ alkyl chains and products containing C ₁₈ alkyl chains ELFACOS

You can also use products from ROHM & HAAS DW It contains a _C20 alkyl chain and has urethane linkages and is sold at 20% dry matter content in water.

Solutions or dispersions of these polymers, in particular in water or in an aqueous-alcoholic medium, may also be used. By way of example of such polymers, mention may be made of the following: 255, 278 and 244. Products DW 1206F and DW 1206J provided by ROHM & HAAS can also be used.

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

As the polyether-polyurethane described above, there may be mentioned polyether-polyurethanes comprising in their chain at least one polyoxyethylenated hydrophilic block and at least one hydrophobic block containing at least one sequence selected from aliphatic sequences, alicyclic sequences and aromatic sequences.

It may be preferred that the polyether-polyurethane comprises at least two hydrocarbon-based lipophilic chains having 8 to 30 carbon atoms separated by a hydrophilic block, and wherein the hydrocarbon-based chains are selected from side chains and chains at the ends of the hydrophilic blocks.

According to one particular form of the invention, use is made of a polyether-polyurethane obtainable by polycondensation of at least three compounds comprising (i) at least one polyethylene glycol containing 150 to 180 mol of ethylene oxide, (ii) a polyoxyethylated stearyl alcohol containing 100 mol of ethylene oxide and (iii) a diisocyanate.

Such polyurethanes/polyethers are marketed in particular by the company Elementis under the name Rheolate FX and Rheoluxe 8118, which is a polycondensate of polyethylene glycol containing 136 mol of ethylene oxide, stearyl alcohol polyoxyethylated with 100 mol of ethylene oxide, and hexamethylene diisocyanate (HDI) having a weight average molecular weight of 40,000 (INCI name: PEG-136/steareth-100/HDI copolymer).

According to another particular form of the invention, use is made of a polyether-polyurethane obtainable by polycondensation of at least three compounds comprising (i) at least one polyethylene glycol containing 150 to 180 mol of ethylene oxide, (ii) stearyl alcohol or decanol and (iii) at least one diisocyanate.

Such polyurethanes/polyethers are marketed in particular by the company Rohm & Haas under the name Aculyn and Aculyn Sale.

Aculyn with the INCI name PEG-150/Stearyl Alcohol/SMDI Copolymer It is a polycondensate of polyethylene glycol containing 150 or 180 mol of ethylene oxide, stearyl alcohol and methylene bis(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 (PEG-150/Decanol/SMDI Copolymer) is a polycondensate of polyethylene glycol containing 150 mol or 180 mol of ethylene oxide, decanol and methylene bis(4-cyclohexyl isocyanate) (SMDI) at 35 wt. % in a mixture of propylene glycol (39 %) and water (26 %) (INCI name: PEG-150/Decanol/SMDI Copolymer).

As the associative polyurethane, a compound represented by the following formula (1) can be preferably used:

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

wherein ^R1 represents a hydrocarbon group, ^R2 and ^R4 independently represent an alkylene group having 2 to 4 carbon atoms (the alkylene groups may be the same as or different from each other) or a styrene group, ^R3 represents a hydrocarbon group which may optionally have a urethane bond, ^R5 represents a branched hydrocarbon group or a secondary 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 represented by the general formula (1) shown above is obtained, for example, by reacting at least one polyether polyol represented by the formula ^R1 -[(O- ^R2 ) _k -OH] _m , at least one polyisocyanate represented by the formula ^R3- (NCO) _h+1 and at least one polyether monool represented by the formula HO-( ^R4 -O) _n - ^R5 .

In such a case, R1 to ^R5 in the general formula (1) are determined by the compounds ^R1 -[(O- ^R2 ) _k -OH] _m , ^R3- (NCO) _h+1 and HO-( ^R4 -O) _n - ^R5 . The charging ratio among the three compounds is not particularly limited, and should preferably be selected so that the ratio of the isocyanate group derived from the polyisocyanate to the ^hydroxyl group derived from the polyether polyol and the polyether monool is within the range of NCO/OH between 0.8:1 and 1.4:1.

The polyether polyol compound represented by the formula ^R1 -[(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 m-hydroxy polyol with alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide or epichlorohydrin or with styrene oxide or the like.

The polyol should preferably be a dihydric to octahydric polyol. Examples of the dihydric to octahydric polyols include dihydric alcohols such as ethylene glycol, propylene glycol, butylene glycol, 1,6-hexanediol, and neopentyl 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-pentanetritol, 2,3,4,5-hexanetritol, 1,2,4,5-pentanetritol and 1,3,4,5-hexanetritol; pentahydric alcohols such as forsauryl alcohol, arabitol and xylitol; hexahydric alcohols such as dipentaerythritol, sorbitol, mannitol and iditol; and octahydric alcohols such as sucrose.

Furthermore, R ² is determined by the alkylene oxide, styrene oxide, etc. subjected to addition. In particular, an alkylene oxide or styrene oxide having 2 to 4 carbon atoms is preferred in terms of availability and excellent effects.

The alkylene oxide, styrene oxide, etc. to be subjected to addition may be subjected to single polymerization or random polymerization or block polymerization of at least two members. The procedure of addition may be a conventional procedure. In addition, the degree of polymerization k may be selected in the range of 0 to 1,000, preferably in the range of 1 to 500, and more preferably in the range of 10 to 200. In addition, the ratio of ethylene groups occupying R ² should preferably be in the range of 50-100% by mass relative to the total amount of R ^2. In such a case, an associative thickener suitable for the purpose of the present invention is obtained.

Furthermore, the molecular weight of the polyether polyol compound represented by the formula R ¹ —[(O—R ² ) _k —OH] _m should preferably be selected within the range of 500 to 100,000, and should more preferably be selected within the range of 1,000 to 50,000.

The polyisocyanate represented by the formula ^R3- (NCO) _h+1 and which can be preferably used to obtain the hydrophobically modified polyether polyurethane represented by the general formula (1) employed in accordance with the present invention is not particularly limited as long as the polyisocyanate has at least two isocyanate groups in the molecule. Examples of the polyisocyanate include aliphatic diisocyanates, aromatic diisocyanates, alicyclic diisocyanates, biphenyl diisocyanate, phenylmethane diisocyanate, phenylmethane triisocyanate and phenylmethane tetraisocyanate.

Furthermore, dimers and trimers (isocyanurate bonds) of the polyisocyanates listed above may be used. In addition, biuret obtained by reaction with amines may be used.

In addition, the polyisocyanates with urethane bonds obtained by the reaction of the aforementioned polyisocyanate compounds and polyols can be used. As polyols, dihydroxy polyols to octahydroxy polyols are preferred, and the polyols listed above are preferred. In the case where trihydroxy polyisocyanates or more hydroxy polyisocyanates are used as the polyisocyanates represented by the formula R ³ —(NCO) _n+1 , the aforementioned polyisocyanates with urethane bonds are preferably used.

The polyether monool represented by the formula HO-( ^R4 -O) _n - ^R5 and which can be preferably used to obtain the hydrophobically modified polyether polyurethane represented by the general formula (1) used in accordance with the present invention is not particularly limited as long as the polyether monool is a polyether of a linear monool, a branched monool or a secondary monool. The polyether monool can be obtained by addition polymerization of a linear monool, a branched monool or a secondary monool with an alkylene oxide (e.g., ethylene oxide, propylene oxide, butylene oxide or epichlorohydrin) or with styrene oxide or the like.

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

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

Polyacrylate cross-linked polymer

The term "polyacrylate cross-linked polymer" as used in this application refers to a copolymer of acrylic acid, methacrylic acid or one of their esters cross-linked by dimethacrylate glycol.

The following is a non-limiting list of polyacrylate cross-linked polymers that can be used in the compositions of the present invention.

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

Polyacrylate Crosspolymer-2 is a copolymer of PEG/PPG-23/6 dimethicone citraconate, _C10-30 alkyl PEG-25 methacrylate, and one or more monomers of acrylic acid, methacrylic acid, or one of their simple esters, crosslinked with trimethylolpropane PEG-15 triacrylate. This copolymer is commercially available from Lubrizol Advanced Materials, Inc. (Cleveland, Ohio) under the trade name Fixate Superhold Polymer.

Polyacrylate crosspolymer-3 is a copolymer of butyl acrylate, PEG-10 acrylate, PPG-6 acrylate, and dimethyl acrylamide crosslinked by PEG-23 diacrylate. This copolymer is commercially available from Goo Chemical Company, Ltd. (Kyoto, Japan) under the trade name Plascize L-64S.

Polyacrylate Crosspolymer-4 is a copolymer of sodium acryloyldimethyltaurate, dimethylacrylamide, sodium acrylate, acrylic acid, and hydroxyethyl acrylate crosslinked with methylenebisacrylamide. This copolymer is commercially available from Seppic (Paris, France) under the trade name Sepinov P500.

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

Polyacrylate crosspolymer-6 is a copolymer of ammonium acryloyldimethyltaurate, dimethylacrylamide, lauryl methacrylate, and laureth-4 methacrylate crosslinked with trimethylolpropane triacrylate. This copolymer is commercially available from Seppic Affaires Reglementaires (Puteux, France) under the trade name Sepimax Zen.

Polyacrylate crosspolymer-7 is a copolymer of methacrylate PPG-6 phosphate and one or more monomers of acrylic acid, methacrylic acid, or one of their simple esters crosslinked with dimethicone PEG/PPG-25/29 acrylate. This copolymer is commercially available from Momentive Performance Materials (Friendly, W.Va.) under the trade name Y-17552.

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

Polyacrylate Crosspolymer-9 is a copolymer of tert-butylaminoethyl methacrylate and carboxyethyl acrylate crosslinked by a combination of pentaerythritol tetraacrylate and a hexafunctional acrylate formed by reacting pentaerythritol triacrylate with toluene diisocyanate.

Polyacrylate Crosspolymer-10 is a crosslinked polymer prepared by polymerizing a mixture of trimethoxysilylpropyl methacrylate and trimethylolpropane trimethacrylate.

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

Polyacrylate Crosspolymer-12 is a copolymer of t-butyl methacrylate, stearyl methacrylate, methoxy PEG-23 methacrylate, and dimethyl acrylamide cross-linked with methylene bisacrylamide.

Polyacrylate crosspolymer-14 is a copolymer of acrylic acid, lauryl methacrylate, cetyl methacrylate, stearyl methacrylate, and phosphorylcholine diol methacrylate crosslinked by allyl ether of pentaerythritol. This copolymer is commercially available from KCl Ltd. (Seoul, South Korea) under the trade name Phosphomer ST610KC.

According to some embodiments, the composition according to the present invention comprises a polyacrylate cross-linked polymer selected from the group consisting of polyacrylate cross-linked polymer-1, polyacrylate cross-linked polymer-2, polyacrylate cross-linked polymer-3, polyacrylate cross-linked polymer-4, polyacrylate cross-linked polymer-5, polyacrylate cross-linked polymer-6, polyacrylate cross-linked polymer-7, polyacrylate cross-linked polymer-8, polyacrylate cross-linked polymer-9, polyacrylate cross-linked polymer-10, polyacrylate cross-linked polymer-11, polyacrylate cross-linked polymer-12, polyacrylate cross-linked polymer-14, and combinations thereof.

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

More preferably, the composition according to the invention comprises a hydrophobically associating water-soluble polymer chosen from Polyacrylate Crosspolymer-6, Steareth-100/PEG-136/HDI Copolymer, PEG-240/HDI Copolymer Bis-Decyltetraceth-20 Ether, and combinations thereof.

If present, the hydrophobically associating water-soluble polymer is advantageously present in an amount ranging from 0.1 wt.% to 10 wt.%, preferably from 0.5 wt.% to 5 wt.%, more preferably from 0.3 wt.% to 3 wt.%, relative to the total weight of the composition.

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

(i) 0.5 wt.% to 5 wt.% of arachidyl alcohol (and) behenyl alcohol (and) arachidyl glucoside;

(ii) 0.5 wt.% to 5 wt.% of polyglyceryl-6 distearate (and) jojoba esters (and) cetyl alcohol (and) polyglyceryl-3 beeswax;

(iii) 0.1 wt.% to 2 wt.% of a compound selected from 2-oleylamino-1,3-octadecanediol and ceramide NP;

(iv) 1 wt.% to 5 wt.% of hydroxypropyltetrahydropyrantriol; and

(v) 0.3 wt.% to 3 wt.% of a hydrophobically associating water-soluble polymer selected from the group consisting of polyacrylate crosspolymer-6, steareth-100/PEG-136/HDI copolymer, PEG-240/HDI copolymer, bis-decyltetradeceth-20 ether, and combinations thereof.

Galenic form and method

The compositions of the invention are in the form of oil-in-water emulsions.

The composition according to the invention has a layered structure.

The term "lamellar structure" refers to a liquid crystal structure, or a swelled or non-swelled crystalline lamellar hydrate phase with a plane symmetry, which comprises several amphiphilic bilayers arranged in parallel and separated by a liquid medium, usually water. As shown in Figures 1 and 2, the lamellar structure has a characteristic optical effect when observed with an optical microscope under 90° cross-polarized light with a unique optical effect. If a unique optical effect is observed, it means that a lamellar structure is formed.

The compositions according to the invention can be used for caring for keratin materials.

According to a second aspect, the present invention provides a non-therapeutic method for caring for keratin materials, which comprises applying to the keratin material a composition according to the first aspect of the invention.

The following examples serve to illustrate the present invention, however, they are not limiting.

Example

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

Table 1

Inventive Example 1-2 and Comparative Example 1-2

The compositions of Inventive Examples (IE.) 1-2 and Comparative Examples (CE.) 1-2 were prepared according to the amounts given in Table 2. The amount of each component is given as % by weight of the total weight of the composition in which it is contained.

Table 2

Arachidyl alcohol (and) behenyl alcohol (and) arachidyl glucoside ¹⁾ : comprising 55 wt.% of arachidyl alcohol, 30 wt.% of behenyl alcohol and 15 wt.% of arachidyl glucoside.

Polyglyceryl-6 distearate (and) jojoba esters (and) cetyl alcohol (and) polyglyceryl-3 beeswax: containing 64wt.% polyglyceryl-6 distearate, 19wt.% jojoba esters, 8.5wt.% cetyl alcohol and 8.5wt.% polyglyceryl-3 beeswax

Preparation method:

Taking the composition of Inventive Example 1 as an example, the composition listed above was prepared as follows:

1). The ingredients for the aqueous phase (glycerin, sodium di(laurylamide glutamine) lysine, phenoxyethanol and water) were mixed using a homogenizer and heated to 70°C.

2). Using a homogenizer, arachidyl alcohol (and) behenyl alcohol (and) arachidyl glucoside, polyglyceryl-6 distearate (and) jojoba esters (and) cetyl alcohol (and) polyglyceryl-3 beeswax, 2-oleylamino-1,3-octadecanediol, C15-19 alkane, and hexadecanol were mixed to obtain a mixture, and heated to 70°C.

3). The mixture was introduced into the aqueous phase and homogenized at 60°C for 10 min to obtain an oil-in-water emulsion.

4). Add polymer (PEG-240/HDI copolymer bis-decyltetradecyl alcohol polyether-20 ether and polyacrylate crosspolymer-6) to the emulsion and homogenize for 10 minutes.

5). The emulsion was transferred to a disperser and cooled to room temperature, while stirring was continued and hydroxypropyl tetrahydropyrantriol was added.

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

Evaluate

Each composition of Inventive Examples 1-2 and Comparative Examples 1-2 was evaluated in terms of lamellar structure, skin barrier function, and skin modification.

Layered structure

Whether a lamellar structure is formed is evaluated as follows.

The composition was observed using a Leica DLMB microscope under 90° crossed polarized light and a microscope picture was taken. If the characteristic optical effect of a lamellar structure was observed, it means that a lamellar structure was formed.

FIG. 1 shows a photograph of the composition of Inventive Example 1 (IE.1) taken using a polarized light microscope.

FIG. 2 shows a photograph of the composition of Inventive Example 2 (IE.2) taken using a polarized light microscope.

Skin Retouching

The skin modification provided by each composition of Inventive Examples 1-2 and Comparative Examples 1-2 was evaluated in the following manner: 10 Chinese female volunteers were invited to apply each composition on their faces and score the skin modification on a scale of 1-5 and average the scores, where 1 represents very greasy skin modification and 5 represents very fresh skin modification. All 10 volunteers reported the ratings of the skin modification 10 minutes after application.

The layer structure of each composition prepared above and the skin modification results provided are listed in Table 3.

Table 3

project IE.1 IE.2 CE.1 CE.2 Layered structure yes yes yes yes Skin Retouching 4 4 2 3

NA: Not Observed

Transepidermal water loss (TEWL)

The transepidermal water loss (TEWL) of the compositions of Inventive Examples 1-2 and Comparative Examples 1-2 and a commercial product (LaMer concentrate serum from Estee Lauder) was measured on the forearms of 6 female volunteers aged 18-40 using a vapometer as follows.

18 μl (2 mg/cm ² ) of each tested sample was transferred and gently spread evenly on each 3*3 cm ² test area. And the transepidermal water loss (TEWL) obtained on an untreated area was used as a blank control.

A lower TEWL indicates better skin barrier function.

The results are summarized in Table 4.

Table 4

nature IE.1 IE.2 CE.1 CE.2 Commercial Products Blank control TEWL (8h,%) -45.39 -38.50 -31.75 -32.20 -27.63 -0.45

It can be seen that compared with the compositions of Comparative Examples 1-2 and the commercial products, the compositions of Inventive Examples 1-2 provide better skin barrier function.

Claims (14)

1. A composition in the form of an oil-in-water emulsion for the care of keratin materials, comprising: (i) at least one nonionic surfactant selected 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 polyglycerol diester; and (iii) at least one ceramide-type compound. 2. The composition according to claim 1, wherein the sugar ether is an alkyl polyglycoside having the following formula (I): R(O)(G) _n (I) in: R is a linear or branched C _8-22 alkyl group, preferably a C _8-16 alkyl group; 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 The range of n is 1-5, preferably 1.05-2. 3. A composition according to claim 2, wherein the alkyl polyglycoside is used as a mixture with a fatty alcohol having 8 to 30 carbon atoms, for example 10 to 20 carbon atoms, wherein the alkyl polyglycoside and the fatty alcohol have similar carbon atoms, the difference being less than 5, or less than 2, or 0. 4. The composition of claim 3, wherein the mixture of alkyl polyglycoside and fatty alcohol is selected from the group consisting of myristyl alcohol/myristyl glucoside, isostearyl alcohol/isostearyl glucoside, cetearyl alcohol/cetearyl glucoside, cetearyl alcohol/cocoyl glucoside, arachidyl alcohol/behenyl alcohol/arachidyl glucoside, arachidyl alcohol/behenyl alcohol/arachidyl glucoside, _C14-22 alcohol/ _C14-22 alkyl glucoside and coconut alcohol/cocoyl glucoside. 5. The composition according to any one of claims 1 to 4, wherein the nonionic surfactant selected from sugar ethers of _C8 - _C22 fatty alcohols is present in an amount ranging from 0.1 wt.% to 10 wt.%, preferably 0.5 wt.% to 5 wt.%, more preferably 0.5 wt.% to 5 wt.%, relative to the total weight of the composition. 6. The cosmetic composition according to any one of claims 1 to 5, wherein the ester type nonionic surfactant comprises: i) at least one monounsaturated ester of formula (II) R1-C(O)-O-R2(II) in: R1 and R2 each represent a C18-C44 fatty chain, at least one of R1 or R2 is monounsaturated; and ii) at least one polyglycerol diester of formula (III) R3-C(O)-(O-CH2-CH(OH)-CH2)n-O-C(O)-R4(III) in: R3 and R4 represent a linear or branched saturated C18-C44 fatty chain, Preferably, the ester type nonionic surfactant comprises at least one monounsaturated ester of formula (II), wherein R1 and R2 represent C18-C30 fatty chains respectively, and at least one of R1 or R2 is monounsaturated; and at least one polyglycerol diester of formula (III), wherein R3-C(O)- and R4 each represent a linear or branched saturated C20-C34 fatty chain, More preferably, the ester type nonionic surfactant is a mixture of polyglyceryl-6 distearate, jojoba esters, polyglyceryl-3 beeswax and cetyl alcohol. 7. A composition according to any one of claims 1 to 6, wherein the ester type nonionic surfactant is present in an amount ranging from 0.1 wt.% to 10 wt.%, preferably from 0.5 wt.% to 5 wt.%, more preferably from 0.5 wt.% to 5 wt.%, relative to the total weight of the composition. 8. The composition according to any one of claims 1 to 7, wherein the ceramide-type compound corresponds to the general formula (I): in: -R ₁ means: - a saturated or unsaturated and linear or branched C ₁ -C ₅₀ hydrocarbon group, preferably a C ₅ -C ₅₀ hydrocarbon group, which may be substituted by one or more hydroxyl groups optionally esterified with an acid R ₇ COOH, R ₇ is an optionally monohydroxylated or polyhydroxylated, saturated or unsaturated and linear or branched C ₁ -C ₃₅ hydrocarbon group, one or more hydroxyl groups of the R ₇ group may be esterified with an optionally monohydroxylated or polyhydroxylated, saturated or unsaturated and linear or branched C ₁ -C ₃₅ fatty acid; - or R"-(NR-CO)-R' group, wherein R represents a hydrogen atom, or a monohydroxylated or polyhydroxylated C ₁ -C ₂₀ hydrocarbon group, preferably a monohydroxylated C ₁ -C ₂₀ hydrocarbon group, R' and R" are hydrocarbon groups, the sum of their carbon atoms being between 9 and 30, and R' is a divalent group; - or R ₈ -O-CO-(CH ₂ ) _p group, wherein R ₈ represents a C ₁ -C ₂₀ hydrocarbon group, and p is an integer ranging from 1 to 12; - _R2 is selected from a hydrogen atom; a glycosyl group, in particular a (glycosyl) _n , (galactosyl) _m or sulfogalactosyl group, a sulfate residue or a phosphate residue, a phosphoethylamine group and a phosphoethylammonium group, wherein n is an integer varying from 1 to 4, and m is an integer varying from 1 to 8; - R ₃ represents a hydrogen atom, or a hydroxylated or non-hydroxylated and saturated or unsaturated C ₁ -C ₃₃ hydrocarbon group, one or more hydroxyl groups may be esterified by an inorganic acid or acid R ₇ COOH, R ₇ has the same meaning as above, and one or more hydroxyl groups may be etherified by (glycosyl) _n , (galactosyl) _m , sulfogalactosyl, phosphoethylamine group or phosphoethylammonium group, and R ₃ may also be substituted by one or more C ₁ -C ₁₄ alkyl groups; Preferably, R ₃ represents a C ₁₅ -C ₂₆ α-hydroxyalkyl group, the hydroxy group being optionally esterified with a C ₁₆ -C ₃₀ α-hydroxy acid; -R ₄ represents a hydrogen atom, a methyl group or an ethyl group; an optionally hydroxylated, saturated or unsaturated and linear or branched C ₃ -C ₅₀ hydrocarbon group; or a -CH ₂ -CHOH-CH ₂ -OR ₆ group, wherein R ₆ represents a C ₁₀ -C ₂₆ hydrocarbon group; or a R ₈ -O-CO-(CH ₂ ) _p group, wherein R ₈ represents a C ₁ -C ₂₀ hydrocarbon group, and p is an integer varying from 1 to 12; - R ₅ represents a hydrogen atom or an optionally monohydroxylated or polyhydroxylated, saturated or unsaturated and linear or branched C ₁ -C ₃₀ hydrocarbon group, one or more of which may be etherified by a (glycosyl) _n , (galactosyl) _m , sulfogalactosyl, phosphoethylamine or phosphoethylammonium group; The proviso is 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 group. 9. The composition according to any one of claims 1 to 7, wherein the ceramide-type compound is selected from: -2-N-linoleamidooctadecane-1,3-diol, -2-N-oleoylaminooctadecane-1,3-diol, -2-N-palmitoylaminooctadecane-1,3-diol, -2-N-stearoylaminooctadecane-1,3-diol, -2-N-Behenamidooctadecane-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 combinations thereof. 10. The composition according to any one of claims 1-9, wherein the ceramide-type compound is present in an amount ranging from 0.01 wt.% to 10 wt.%, preferably 0.05 wt.% to 5 wt.%, more preferably 0.1 wt.% to 2 wt.%, relative to the total weight of the composition. 11. The composition of any one of claims 1-10, further comprising a hydrophobically associative water-soluble polymer selected from the group consisting of nonionic associative polyether-polyurethanes, polyacrylate cross-linked polymers, and combinations thereof. 12. The composition according to claim 11, wherein the hydrophobically associating water-soluble polymer is present in an amount ranging from 0.1 wt.% to 10 wt.%, preferably from 0.5 wt.% to 5 wt.%, more preferably from 0.3 wt.% to 3 wt.%, relative to the total weight of the composition. 13. The composition according to claim 1, comprising, relative to the total weight of the composition: (i) 0.5 wt.% to 5 wt.% of arachidyl alcohol (and) behenyl alcohol (and) arachidyl glucoside; (ii) 0.5 wt.% to 5 wt.% of polyglyceryl-6 distearate (and) jojoba esters (and) cetyl alcohol (and) polyglyceryl-3 beeswax; (iii) 0.1 wt.% to 2 wt.% of a compound selected from 2-oleamido-1,3-octadecanediol and ceramide NP; (iv) 1 wt.% to 5 wt.% of hydroxypropyltetrahydropyrantriol; and (v) 0.3 wt.% to 3 wt.% of a hydrophobically associating water-soluble polymer selected from the group consisting of polyacrylate crosspolymer-6, steareth-100/PEG-136/HDI copolymer, PEG-240/HDI copolymer, bis-decyltetradeceth-20 ether, and combinations thereof. 14. Non-therapeutic method for caring for keratin materials, comprising applying to said keratin materials a composition according to any one of claims 1 to 13.