CARE COMPOSITION OF KERATINOUS MATERIALS

A composition with neohesperidin dihydrochalcone, C-glycosides, and carnosine compounds addresses the need for effective skin barrier repair and anti-aging, enhancing skin firmness and reducing water loss.

FR3140266B1Active Publication Date: 2025-10-24LOREAL SA
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Patent Information

Application Number
FR2022011941
Authority / Receiving Office
FR · FR
Patent Type
Patents
Current Assignee / Owner
Priority Date
2022-09-30
Filing Date
2022-11-17
Publication Date
2025-10-24
Estimated Expiration
2042-11-17

AI Technical Summary

Technical Problem

There is a lack of cosmetic products that effectively provide a repairing and anti-aging effect on the skin barrier.

Method used

A composition comprising neohesperidin dihydrochalcone, C-glycosides, and carnosine compounds, which are applied to keratinous materials to enhance skin firmness and reduce transdermal water loss, thereby improving the skin barrier function.

Benefits of technology

The composition exhibits significant anti-aging attributes with improved skin firmness and reduced transdermal water loss, indicating better skin barrier function.

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Abstract

COMPOSITION FOR CARE OF KERATINOUS MATERIALS The present invention relates to a composition for care of keratinous materials, comprising: (i) neohesperidin dihydrochalcone; (ii) at least one C-glycoside; and (iii) at least one carnosine compound. The present invention also relates to a non-therapeutic method for caring for keratinous materials, comprising the application of said composition to the keratinous materials. Figure for abstract: Figure 1
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Description

Title of the invention: COMPOSITION FOR CARE OF KERATINOUS MATERIALS Technical field The present invention relates to a cosmetic composition. In particular, the present invention relates to a composition for caring for keratinous materials. The present invention also relates to a non-therapeutic method for caring for keratinous materials. RELATED ART The skin is the human body's protective barrier. It protects the inside of the body from physical damage (such as trauma) and biological damage (such as that caused by bacteria, viruses, or fungi). The development of formulas dedicated to skin care is ongoing. It is also known for using active ingredients in cosmetic products to treat or care for the skin, such as cleansing, moisturizing, providing a skin barrier, anti-aging, minimizing pores, etcetera. Among them, providing a skin barrier and anti-aging are always centers of interest for consumers worldwide. However, there is no such cosmetic product that can effectively provide a repairing and anti-aging effect on the skin barrier. It is desirable to have cosmetic products that can provide a restorative and anti-aging effect on the skin barrier. Summary of the invention The inventors have now discovered that it is possible to formulate compositions that offer a repairing and anti-aging effect on the skin barrier. Accordingly, in a first aspect, the present invention provides a composition for caring for keratinous materials, comprising: (i) neohesperidin dihydrochalcone; (ii) at least one C-glycoside chosen from the compounds of formula (I): X—R (I) S—' w in which: - R represents a saturated C1 to C10 alkyl radical, in particular C1 to C4 which may optionally be replaced by at least one radical chosen from OH, COOH or COOR" 2 R"2 being a saturated C1-C4 alkyl radical>

[0013] - 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 hydroxyl group which is necessarily free and optionally one or more protected amine functional groups, and

[0014] - 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)-,

[0015] the S-CH2-X bond represents a bond of C-anomeric nature, which can be α or [3,

[0016] as well as their physiologically acceptable salts, their solvates, such as hydrates and their optical and geometric isomers; and

[0017] (iii) at least one camosine compound.

[0018] The inventors have discovered that the composition of the present invention exhibits significantly better relevant anti-aging attribute, such as improved skin firmness and exhibits much lower transdermal water loss, which represents better skin barrier function.

[0019] 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.

[0020] Other advantages of the present invention will appear more clearly on reading the description and examples which follow. Brief description of the drawings

[0021] Implementations of the present invention will now be described, by way of example only, with reference to the accompanying figure, in which:

[0022] [Fig-1] [Fig.l] shows sensory profiles of the compositions of the example Inventive Example 5 and Comparative Example 3, wherein the solid line represents the composition of Inventive Example 5, and the dotted line represents the composition of Comparative Example 3. DETAILED DESCRIPTION OF THE INVENTION

[0023] Unless otherwise indicated, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art in the field to which the present invention relates. Where the definition of a term in the present invention conflicts with the meaning commonly understood by those skilled in the art in the field to which the present invention relates, the definition described in the present invention shall apply.

[0024] 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 "from...to...".

[0025] Furthermore, the expression “at least one” used in the present description is equivalent to the expression “one or more”.

[0026] Throughout the present application, the term "comprising" should be interpreted as encompassing all the specifically mentioned features as well as optional, additional and unspecified features. As used herein, the term "comprising" also refers to the embodiment in which no features other than the specifically mentioned features are present (i.e. "consisting of").

[0027] Unless otherwise indicated, all numbers expressing amounts of ingredients, reaction conditions and the like, used in the description and claims are to be understood as being modified in all cases by the term "about". Therefore, unless otherwise indicated, the numerical values ​​and parameters described herein are approximate values ​​which may be modified depending on the intended purpose, if necessary.

[0028] For the purposes of the present invention, the term "keratinous materials" is intended to cover human skin and mucous membranes such as the lips. Facial skin is particularly considered according to the present invention.

[0029] In the present invention, all percentages refer, unless otherwise indicated, to a weight percentage.

[0030] According to a first aspect, the present invention provides a composition for caring for keratinous materials, comprising:

[0031] (i) neohesperidin dihydrochalcone;

[0032] (ii) at least one C-glycoside; and

[0033] (iii) at least one camosine compound. Neohesperidin dihydrochalcone

[0034] According to the first aspect, the composition of the present invention comprises Neohesperidine dihydrochalcone.

[0035] Neohesperidin dihydrochalcone (DHC) is a naturally occurring polyphenol with high antioxidant potential across a very broad spectrum of several radical species, which is capable of acting on three cellular targets: membrane, nucleus and cytoplasm.

[0036] Neohesperidin dihydrochalcone (DHC) is a member of the dihydrochalcone family, which is part of the flavonoid class. Neohesperidin DHC is a glycosylated flavonoid with the following structure: OH

[0037] It is also known as IUP AC: 1-(4-((2-O-[6-deoxy-aL-mannopyranosyl]-[3-D-glucopyranosyl)oxy)-2,6-dihydroxyphenyl)-3-[3-hydroxy-4-methoxyphenyl]-1-propanone.

[0038] Neohesperidin DHC (CAS number 20702-77-6) can notably be obtained either from neohesperidin which can be extracted from bitter orange (Citrus aurantium) or from naringin which is obtained from grapefruit (Citrus paradisii). Synthesis from extracted neohesperidin involves hydrogenation in the presence of a catalyst under alkaline conditions. The synthesis of naringin is based on its conversion to phloroacetophenone-4'-[3-neohesperidoside, which can be condensed with risovanillin (3-hydroxy-4-methoxybenzaldehyde) to produce neohesperidin (see the following references: Borrego, F. Sweeteners (3rd edition), 2007, 67-77 and Borrego, F; Montijano, H. Food Science and Technology, 2001, 112 (Alternatives Sweeteners), 87-104).

[0039] Neohesperidin dihydrochalcone is notably available under the commercial reference Neohesperidin DC from HEALTHTECH BIOACTIVES (FERRER).

[0040] Neohesperidin dihydrochalcone can exist in hydrate form.

[0041] Preferably, the neohesperidin dihydrochalcone is present in an amount ranging from 0.01% to 10% by weight, preferably from 0.01% to 5% by weight, more preferably from 0.01% to 3% by weight, relative to the total weight of the composition. C-glycosides

[0042] According to the first aspect, the composition of the present invention comprises at least one C-glycoside chosen from the compounds of formula (I): X—R (I) s—'

[0043] in which:

[0044] - R represents a saturated C 1 to C 10 alkyl radical, in particular C 1 to C 4 which can optionally be replaced by at least one radical chosen from OH, COOH or COOR" 2 R"2 being a saturated CrC4 alkyl radical

[0045] - 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 hydroxyl group which is necessarily free and optionally one or more protected amine functional groups, and

[0046] - 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)-,

[0047] the S-CH2-X bond represents a bond of C-anomeric nature, which can be α or [3,

[0048] as well as their physiologically acceptable salts, their solvates, such as hydrates and their optical and geometric isomers.

[0049] The C-glycosides used 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, preferably C1 to C2 and more preferably, a methyl radical.

[0050] Mention may in particular be made, among the alkyl groups suitable for implementing the invention, of methyl, ethyl, isopropyl, n-propyl, n-butyl, t-butyl, isobutyl, sec-butyl, pentyl, n-hexyl, cyclopropyl, cyclopentyl or cyclohexyl groups.

[0051] According to one embodiment of the invention, it is possible to use a CC-glycoside corresponding to formula (I) 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 monosaccharide or polysaccharide having at least one free hydroxyl functional group and / or optionally one or more necessarily protected amine functional groups, X and R moreover retaining all the above definitions.

[0052] Advantageously, a monosaccharide of the invention may be chosen from the following elements: 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 designates the following elements: D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose and in particular D-xylose.

[0053] 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 via a 1-4 bond.

[0054] 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.

[0055] Preferably, a C-glycoside of formula I is used for which:

[0056] - R denotes an unsubstituted linear alkyl radical, in Cr C4c in particular a Cr-C2 alkyl radical, in particular a methyl radical;

[0057] - S represents a monosaccharide as described above and selected in particular among D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, and in particular D-xylose;

[0058] - X represents a group chosen from a group -CO-, -CH(OH)- or -CH(NH2) and, preferably a -CH(OH)- group.

[0059] Acceptable salts of the compounds described in the present invention include conventional non-toxic salts of said compounds, such as those formed from organic or inorganic acids. Examples include salts of inorganic acids such as sulfuric acid, hydrochloric acid. Also included are salts of organic acids, which may comprise one or more carboxylic, sulfonic or phosphonic acid groups. Particular mention may be made of propionic acid, acetic acid, terephthalic acid, citric acid and tartaric acid.

[0060] When the compound of formula (I) 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 therefore comprise, for example, one or more alcoholic functional groups; mention may in particular be made 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.

[0061] Solvates that are acceptable for the compounds described in the present invention include conventional solvates, such as those formed during the final stage 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.

[0062] Of course, according to the invention, a CC-glycoside corresponding to formula (I) can be used alone or in a mixture with other C-glycosides and in any proportion.

[0063] A C-glycoside which is suitable for the invention can in particular be obtained by the synthesis process described in document WO 02 / 051828.

[0064] Mention may in particular be made, by way of non-limiting illustration, of the C-glycoside compounds which are particularly suitable for the invention, the following compounds:

[0065] - C-[3-D-xylopyranoside-n-propane-2-one,

[0066] - C-a-D-xylopyranoside-n-propane-2-one,

[0067] - C-[3-D-xylopyranoside-2-hydroxypropane,

[0068] - C-a- D-xylopyranoside-2-hydroxypropane,

[0069] - l-(C-[3-D-fucopyranoside)propane-2-one,

[0070] - l-(C-a-D-fucopyranoside)propan-2-one,

[0071] - l-(C-[3-L-fucopyranoside)propane-2-one,

[0072] - l-(C-a-L-fucopyranoside)propane-2-one,

[0073] - l-(C-[3-D-fucopyranoside)-2-hydroxypropane,

[0074] - l-(C-a-D-fucopyranoside)-2-hydroxypropane,

[0075] - l-(C-[3-L-fucopyranoside)-2-hydroxypropane,

[0076] - l-(C-a-L-fucopyranoside)-2-hydroxypropane,

[0077] - l-(C-[3-D-glucopyranosyl)-2-hydroxypropane,

[0078] - l-(C-a-D-glucopyranosyl)-2-hydroxypropane,

[0079] - l-(C-[3-D-galactopyranosyl)-2-hydroxypropane,

[0080] - l-(CaD-galactopyranosyl)-2-hydroxypropane,

[0081] - l-(C-[3-D-fucofuranosyl)propane-2-one,

[0082] - l-(CaD-fucofuranosyl)propane-2-one,

[0083] - l-(C-[3-L-fucofuranosyl)propane-2-one,

[0084] - l-(CaL-fucofuranosyl)propane-2-one,

[0085] - C-[3-D-maltopyranoside-n-propane-2-one,

[0086] - CaD-maltopyranoside-n-propane-2-one,

[0087] - C-[3-D-maltopyranoside-2-hydroxypropane,

[0088] - CaD-maltopyranoside-2-hydroxypropane, their isomers and their mixtures.

[0089] According to one embodiment, C-[3-D-xylopyranoside-2-hydroxypropane or CaD-xylopyranoside-2-hydroxypropane and more preferably C-[3-D-xylopyranoside-2-hydroxypropane can advantageously be used for the preparation of a composition according to the invention.

[0090] According to a specific embodiment, the C-glycoside may be C-[3-D-xylopyranoside-2-hydroxypropane (or hydroxypropyl tetrahydropyrantriol) provided in the form of a solution containing 70% by weight of active ingredient in water and propylene glycol.

[0091] Advantageously, the C-glycoside is present in the composition in an amount ranging from 0.01 to 25% by weight, preferably from 0.01 to 15% by weight, and more preferably from 0.01% by weight to 10% by weight, relative to the total weight of the composition. Carnosine compounds

[0092] According to the first aspect, the composition of the present invention comprises at least one carnosine compound.

[0093] Preferably, the carnosine compound is chosen from the compounds of formula (II)

[0094] where RI represents H or CH3 and R2 represents H or COOH,

[0095] or their salts.

[0096] According to the present invention, the salts of compounds of formula (II) are preferably salts of compounds of formula (II) with mineral acids, in particular salts of formula (III): (IIII)

[0097] in which n represents 1, 2 or 3 and A represents HCl or HNO3 and RI represents H or CH3 and R2 represents H or COOH.

[0098] The carnosine compounds useful in the composition according to the present invention are known and are accessible by conventional methods of organic chemistry.

[0099] Preferably, the carnosine compound is selected from carnosine, L-carnosine, D-carnosine, D / L-carnosine, carnicine, carnicine HCl salt, anserine, D-anserine, L-anserine, L-anserine HNO3 salt and combinations thereof.

[0100] As a commercial product for camosine, it is possible to mention the one available under the trade name Dragosine® PN 844033 from Symrise.

[0101] Advantageously, the camosine compound is present in an amount ranging from 0.01% by weight to 10% by weight, preferably from 0.01% by weight to 5% by weight, more preferably from 0.01% by weight to 3% by weight, relative to the total weight of the composition.

[0102] Unexpectedly, the inventors discovered that the combination of neohesperidin dihydrochalcone, C-glycoside and camosine compound leads to a significant synergistic effect on the repairing and anti-aging effect of the skin barrier. Anti-redness active ingredients

[0103] Preferably, the composition according to the present invention comprises an anti-redness active ingredient.

[0104] Examples of anti-redness active ingredients include madecassoside, saccharide isomerate, palmitoyl tripeptide-8, panthenol, Oea europaea (olive) leaf extract, Mentha piperita (peppermint) extract, leontopodium alpinum extract, dipotassium glycyrrhizate, acetyl dipeptide-1 cetyl ester, acetyl tetrapeptide-15, boswellia serrata extract, sodium palmitoyl proline (and) nymphaea alba flower extract.

[0105] In some embodiments, the composition of the present invention comprises at least one anti-redness active ingredient selected from madecassoside, saccharide isomerate, palmitoyl tripeptide-8, panthenol, Olea europaea (olive) leaf extract, Mentha piperita (peppermint) extract, Leontopodium alpinum extract, dipotassium glycyrrhizate, acetyl dipeptide-1 cetyl ester, acetyl tetrapeptide-15, Boswellia serrata extract, sodium palmitoyl proline (and) Nymphaea alba flower extract, and a combination thereof.

[0106] In some embodiments, the composition of the present invention comprises leontopodium alpinum extract, in particular, leontopodium alpinum callus culture extract, as an anti-redness active ingredient.

[0107] If present, advantageously, the anti-redness active ingredient is present in the composition in an amount ranging from 0.01% to 10% by weight, preferably from 0.01% to 5% by weight, more preferably from 0.01% to 3% by weight, relative to the total weight of the composition. Truffle extracts

[0108] Preferably, the composition of the present invention comprises a truffle extract.

[0109] Truffle is the common name given to the edible fruiting body of a corhizian ascomyscete fungus, which takes a more or less globular shape. The fungus can produce several truffles.

[0110] The truffle(s) that can be used in the context of the invention are preferably truffles of the genus Tuber, of the Tuberaceae family, in the Pezizales order. There are more than a hundred species. Among these, we can notably cite the black truffle (Périgord) (Tuber melanosporum), the white truffle (Piedmont) (Tuber magnatum), the white truffle (summer) (Tuber aestivum), the winter truffle (Tuber Brumale), the bianchetto truffle (Tuber borchii) or even the Chinese truffles (Tuber sinensis and Tuber indicum).

[0111] According to a particular embodiment, the truffle(s) used in the context of the invention are chosen from white truffles and black truffles. According to a preferred embodiment, the truffle(s) used in the context of the invention are the black truffle (Périgord) (Tubermelanosporum), the white truffle (summer) (Tuberaestivum), or a mixture of the two.

[0112] In the context of the invention, the truffle extract(s) may in particular be obtained from an extraction solvent using an extraction technique chosen from the extraction techniques well known in the prior art.

[0113] Generally, the extraction solvent is chosen from water-soluble or water-miscible solvents (hydrophilic solvents) and mixtures thereof.

[0114] Among the hydrophilic solvents, mention may be made in particular of substantially linear or branched lower monoalcohols comprising from 1 to 8 carbon atoms, such as ethanol, propanol, butanol, isopropanol or isobutanol; polyols, such as propylene glycol, isoprene glycol, butylene glycol, propylene glycol, glycerol, sorbitol, polyethylene glycols and their derivatives; and mixtures thereof.

[0115] When the extraction solvent is water, the truffle extract is said to be aqueous.

[0116] When the extraction solvent is a substantially linear or branched monoalcohol lower containing 1 to 8 carbon atoms, the truffle extract is said to be alcoholic.

[0117] When the extraction solvent is a polyol, the truffle extract is said to be glycolic.

[0118] When the extraction solvent is a mixture of water and one or more substantially linear or branched lower monoalcohols containing 1 to 8 carbon atoms, the extract is said to be aqueous-alcoholic.

[0119] When the extraction solvent is a mixture of water and one or more polyols, the extract is said to be aqueous-glycolic.

[0120] In the context of the invention, the truffle extract(s) are obtained from an extraction solvent comprising water. The truffle extract(s) are then aqueous, aqueous-alcoholic or aqueous-glycolic. Preferably, the truffle extract(s) are aqueous or aqueous-glycolic.

[0121] If present, advantageously, the truffle extract is present in an amount ranging from 0.01% to 10% by weight, preferably from 0.01% to 5% by weight, more preferably from 0.01% to 3% by weight, relative to the total weight of the composition. Salvia miltiorrhiza extracts

[0122] Preferably, the composition according to the present invention comprises an extract of Salvia miltiorrhiza.

[0123] Various extracts of Salvia miltiorrhiza have obvious antibacterial and anti-inflammatory effects. In addition, Salvia miltiorrhiza extracts have antioxidant and anti-aging effect.

[0124] The Salvia miltiorrhiza extract contains many components. The Salvia miltiorrhiza extract in the invention comprises tanshinone II A, Danshensu and salvianolic acid, and the weight percentage of tanshinone II A is 1-60%, and the weight percentage of Danshensu is 1-60%, the weight percentage of salvianolic acid is 1-60%; preferably, the weight percentage of tanshinone IIA is 20-40%, the weight percentage of Danshensu is 20-40%, the weight percentage of salvianolic acid is 20-40%.

[0125] In certain embodiments, the composition of the present invention comprises a Salvia miltiorrhiza extract, particularly a Salvia miltiorrhiza leaf extract.

[0126] If present, advantageously, the Salvia miltiorrhiza extract is present in an amount ranging from 0.01% to 10% by weight, preferably from 0.01% to 5% by weight, and more preferably from 0.01% to 3% by weight, relative to the total weight of the composition. Aqueous phase

[0127] The composition of the present invention may comprise an aqueous phase.

[0128] Said aqueous phase comprises water.

[0129] Preferably, the continuous aqueous phase comprises a water-miscible organic solvent (at room temperature to 25°C) chosen from glycols and polyols comprising from 2 to 20 carbon atoms, preferably from 2 to 10 carbon atoms, and preferably from 2 to 6 carbon atoms, such as glycerin, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, caprylyl glycol, dipropylene glycol, diethylene glycol; and mixtures thereof, so as to provide a hydration effect.

[0130] If present, advantageously, the water-miscible organic solvent selected from glycols and polyols is present in the composition in a amount ranging from 0.5% by weight to 20% by weight, preferably from 1% by weight to 10% by weight, relative to the total weight of the composition.

[0131] Preferably, the aqueous phase of the composition of the present invention comprises water and glycerin.

[0132] If present, advantageously, the aqueous phase is present in the composition of the present invention in an amount ranging from 70% by weight to 99.8% by weight, relative to the total weight of the composition. Fat phase

[0133] The composition of the present invention may comprise a fatty phase.

[0134] The fatty phase preferably contains at least one oil, in particular a cosmetic oil. It may also contain other fatty substances.

[0135] The term "oil" means a non-aqueous, water-immiscible compound that is liquid at room temperature (20°C) and atmospheric pressure (760 mmHg).

[0136] Oils can be volatile or non-volatile.

[0137] The term "non-volatile" refers to an oil whose vapor pressure at room temperature and atmospheric pressure is non-zero and is less than 103 mmHg (0.13 Pa).

[0138] For the purposes of the invention, the term “volatile oil” designates any oil which is capable of evaporating on contact with the skin in less than one hour, at room temperature and atmospheric pressure.

[0139] A fatty phase which is suitable for the preparation of the compositions, in particular cosmetic compositions, according to the invention may comprise hydrocarbon oils, silicone oils, fluorinated oils or non-fluorinated oils, or mixtures thereof.

[0140] They can be of animal, vegetable, mineral or synthetic origin.

[0141] For the purposes of the present invention, the expression “silicone oil” means an oil comprising at least one silicon atom and in particular, at least one Si-O group.

[0142] The expression “fluorinated oil” means an oil comprising at least one fluorine atom.

[0143] The term "hydrocarbon oil" means an oil containing mainly hydrogen and carbon atoms.

[0144] The oils may optionally comprise oxygen, nitrogen, sulfur and / or phosphorus atoms, for example in the form of hydroxyl or acid radicals.

[0145] If present, advantageously, the oily phase is present in the composition of the present invention in an amount ranging from 1% by weight to 20% by weight, preferably from 2% by weight to 10% by weight, relative to the total weight of the composition of the present invention. Additional cosmetic active ingredients

[0146] The composition of the present invention may comprise one or more additional cosmetic active ingredients in addition to the cosmetic active ingredients mentioned above.

[0147] Examples of cosmetic active ingredients include 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 its derivatives; alpha-hydroxy acids such as lactic acid or glycolic acid and their derivatives; sunscreens; extracts of algae, fungi, plants, yeasts and bacteria; enzymes; other moisturizing agents such as hydroxyethylurea, agents acting on microcirculation and mixtures thereof.

[0148] It is easy for a person skilled in the art to adjust the amount of the additional cosmetic active ingredient based on the end use of the composition according to the present invention. Additional adjuvants or additives

[0149] The composition of the present invention may also comprise conventional cosmetic adjuvants or additives, for example, perfumes, preservatives (for example, chlorophenesin and phenoxyethanol) and bactericides, pH regulators (for example, citric acid), thickeners such as xanthan gum, acrylamide / sodium acryoyldimethyltaurate copolymer, and mixtures thereof.

[0150] A person skilled in the art can choose 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.

[0151] In certain preferred embodiments, the composition according to the present invention further comprises, relative to the total weight of the composition:

[0152] from 0.01% by weight to 10% by weight, preferably from 0.1% by weight to 5% by weight, more preferably from 0.5% by weight to 3% by weight of cetyl alcohol;

[0153] from 0.01% by weight to 5% by weight, preferably from 0.1% by weight to 2.5% by weight, more preferably from 0.5% by weight to 2% by weight of glyceryl stearate;

[0154] from 0.01% by weight to 5% by weight, preferably from 0.1% by weight to 2.5% by weight, more preferably from 0.5% by weight to 2% by weight of PEG-100 stearate;

[0155] from 0.1% by weight to 20% by weight, preferably from 0.5% by weight to 15% by weight, preferably from 1% by weight to 10% by weight of shea butter;

[0156] 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 1% by weight of tetrasodium glutamate diacetate; and

[0157] from 0.01% by weight to 5% by weight, preferably from 0.1% by weight to 4% by weight, more preferably from 0.4% by weight to 2% by weight of acrylamide / sodium acryloyldimethyltaurate copolymer.

[0158] Such a composition may provide a less smooth texture, which allows the composition of the inventive example to more easily retain its shape and provide a unique appearance.

[0159] According to a particularly preferred embodiment, the present invention provides a composition for caring for keratinous materials comprising, relative to the total weight of the composition:

[0160] (i) from 0.01% by weight to 3% by weight of neohesperidin dihydrochalcone;

[0161] (ii) from 0.01% by weight to 10% by weight of at least one C-glycoside chosen from C-[3-D-xylopyranoside-2-hydroxypropane or CaD-xylopyranoside-2-hydroxypropane, and combinations thereof;

[0162] (iii) from 0.01% by weight to 3% by weight of at least one carnosine compound selected from carnosine, L-carnosine, D-carnosine, D / L-carnosine, carnicine, carnicine HCl salt, anserine, D-anserine, L-anserine, L-anserine HNO3 salt and combinations thereof;

[0163] (iv) from 0.01% by weight to 3% by weight of leontopodium alpinum callus culture extract;

[0164] (iv) from 0.01% by weight to 3% by weight of the extract of tuber aestivum; and

[0165] (v) from 0.01% by weight to 3% by weight of Salvia miltiorrhiza leaf extract. Dosage form and process

[0166] The composition of the present invention may be in the form of a gel, cream, or lotion.

[0167] The composition of the present invention can be used for caring for keratinous materials, for example, human skin, in particular facial skin or skin around the eyes.

[0168] According to the 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.

[0169] The following examples serve to illustrate the present invention without, however, being limiting in nature. EXAMPLES

[0170] The main raw materials used, trade names and their suppliers are listed in Table 1.

[0171] [Tableauxl] Nom INCI Nom commercial Fournisseur HYDROXYPROPYL TÉTRAHY DROPYRANTRIOL MEXORYL SCS NOVEAL CARNOSINE DRAGOSINE® P.N. 844033 SYMRISE NEOHESPERIDIN DIHYDRO CHALCONE NEOHESPERIDI NE DC PHAR. EUR. HEALTHTECH BIOA CTIVES (FERRER) LEONTOPODIUM ALPINUM CALLUS CULTURE EXTRACT MAJESTEM® SEDERMA, CRODA NIACINAMIDE (et) SALVIA MIL TIORRHIZA LEAF EXTRACT COLLREPAIR® DG BC10036 BASF BEAUTY CARE SOLUTION TUBER AESTIVUM EXTRACT WHITE TRUFFEE EXTRACT PG CRODAROM CETYL ALCOHOL LANETTE® 16 BASF GLYCERYL STEARATE (et) P EG-100 STEARATE SIMULSOL™ 165 SEPPIC BUTYROSPERMUM PARKII( SHEA) BUTTER LIPEX® SHEAS OFT AARHUSKARLSH AMN TETRASODIUM GLUTAMATE DIACETATE DISSOLVINE® GL-47-S AKZO NOBEL (NOU RYON) ACRYLAMIDE / SODIUM ACR YLOYLDIMETHYLTAURATE COPOLYMER (et) ISOHEXADE CANE (et) POLYSORBATE 80 SIMULGEL™ 600 SEPPIC XANTHAN GUM KELTROL® CG CP KELCO GLYCERIN BP GLYCERINE ORGANIC CHEMICAL CORPORATION CHLORPHENESIN MACROCIDE-OL MACROCARE Exemples inventifs 1 à 5 et Exemples comparatifs 1 à 3

[0172]

[0173] The compositions of inventive examples (EI) 1 to 5 and comparative examples (CE) 1 to 3 were prepared according to the quantities given in Tables 2 and 3. The quantity of each component is given in % by weight of the total weight of the composition containing it.

[0174] [Tables2] Components ELI EL 2 EI.3 EL 4 EC.l EC.2 Hydroxypropyl Tetrahydropyrantriol1' 0.01 0.875 0.875 0.105 7.35 3.15 Carnosine 0.01 0.2 0.105 0.105 0.1 / Neohesperidin dihydro ochalcone 0.02 0.05 0.05 0.02 / / Leontopodium Alpi num Callus Culture Extract 0.11 1 1 1 / / Tuber Aest ivum Extract 0.11 0.11 0.11 0.11 / / Sa Ivia Miltiorrhiza Leaf Extract 0.02 0.25 0.25 0.25 / / Chlorphenesin 0.2 0.3 0.2 / 0.2 0.27 Glycerin 9 7 5 8.5 6.2 5 Xanthan gum 0.05 0.15 / 0.15 0.25 / Water Qs per 100 Qs per 100 Qs per 100 Qs per 100 Qs per 100

[0175] [Tables3] Components El. 5 EC. 3 Hydroxypropyl Tetrahydropyrantriol 0.875 0.875 Carnosine 0.2 / Neohesperidine Dihydrochalcone 0.05 / Leontopodium Alpi num Callus Culture Extract 1 / Tuber Aestivum Extract 0.11 / Salvia Miltiorrhiza Leaf Extract 0.25 / Cetyl Alcohol 1.5 1.5 Glyceryl Stearate (and) PEG-100 Stearate 2.5 2.5 Butyrospermum Parkii (Shea) Butter 5 5 Glycerin 7 7 Chlorphenesin 0.3 0.3 Xanthan Gum 0.15 0.15 Tetrasodium Glutamate Diacetate 0.1 / Acrylamide / Sodium Acryloyldimethyltaurate Copolymer (and) isohexadecane (and) polysorbate 80 1.2 / Water Qs per 100 Qs per 100

[0176] The compositions of inventive examples 1 to 5 are compositions according to the present invention.

[0177] The composition of Comparative Example 1 does not include neohesperidin dihydrochalcone.

[0178] The composition of Comparative Examples 2-3 does not include neohesperidin dihydrochalcone and carnosine compound.

[0179] Preparation process:

[0180] The above compositions were prepared as follows, taking as an example the composition of Inventive Example 5:

[0181] 1). addition of water, glycerin, chlorphenesin, xanthan gum and glutamate tetrasodium diacetate in a main container with stirring at 65°C to obtain a uniform mixture;

[0182] 2). premixture of cetyl alcohol, GLYCERYL STEARATE (and) PEG-100 STEARATE, Butyrospermum Parkii (Shea) Butter into another container with stirring at 65°C to obtain a uniform oil phase; and transferring the oil phase into the main container with stirring to obtain a uniform combination;

[0183] 3). uniform cooling of the suit to less than 40°C;

[0184] 4). premix of hydroxypropyl tetrahydropyrantriol, carnosine, neohesperidin dihydrochalcone, leontopodium alpinum callus culture extract, tuber aestivum extract and salvia miltiorrhiza leaf extract in a mixture;

[0185] 5). addition of the mixture obtained in 4) into the main container at a temperature below 40°C, with agitation,

[0186] 6). addition of the acrylamide / sodium acryloyldimethyltaurate copolymer (and) isohexadecane (and) polysorbate 80 in the main container at a temperature below 40°C, with stirring to obtain a homogeneous composition. Evaluation

[0187] The compositions of inventive examples (EI) 1 to 4 and comparative examples (CE) 1-2 were evaluated in terms of skin barrier function by transepidermal water loss (TEWL) and anti-aging effect through skin firmness and wrinkle length. Transepidermal water loss (TEWL)

[0188] 33 women aged 30 to 55 years were invited to complete the trial. The compositions to be evaluated were applied evenly to the test area - inner forearm at 2.0 mg / cm2 in a room at 20-22 °C with a relative humidity of 40%-50%.

[0189] Transepidermal water loss (TEWL) was measured using a vapometer at T0 (the time just before application of the test compositions) and Ti h (1 hour after application of the test compositions). According to the single-use method of the test compositions, an increase rate of transepidermal water loss (TEWL) at Tih compared to Toa was used to evaluate the skin barrier function-enhancing effect of the test compositions. Skin firmness

[0190] 63 women aged 30-55 were invited to use test compositions for 4 weeks and evaluated the compositions in terms of skin firmness by dermatologists. Length of wrinkles

[0191] 67 women aged 30-55 were invited to use test compositions for 2 weeks and wrinkle lengths (crow's feet) were measured via Primos 3D at To (the time just before application of the test compositions) and T2W (2 weeks after application of test compositions). The rate of decrease in wrinkle length at T2w compared to Toa was calculated.

[0192] The results on transepidermal water loss (TEWL), skin firmness and wrinkle length were summarized in Table 4 below.

[0193] [Tables4] ELI EL 2 EI.3 EI.4 EC.l EC.2 Skin barrier TEWL increase rate (%) 50.97 65 43.75 47.19 27.5 33.03 Anti-aging Skin firmness increase rate (%) / 12.82 13.8 / 10.91 / Wrinkle length decrease rate (%) / / 18 / 8.29 /

[0194] It can be seen from Table 4 that compared to the compositions of Comparative Examples 1-2, the compositions of Inventive Examples 1-3 provide better skin barrier function and anti-aging effect. Texture

[0195] The compositions of inventive example 5 and comparative example 3 were evaluated by a panel of randomly trained experts regarding 37 attributes. The results were presented in the form of sensory profiles accompanied by their average data. The threshold for significant difference in the test is set at 5% and 10%.

[0196] The sensory profiles of the compositions of inventive example 5 and comparative example 3, have been shown in [Fig.l], where the solid line represents the composition of inventive example 5, and the dotted line represents the composition of comparative example 3.

[0197] It can be seen in [Fig.l] that the composition of inventive example 5 has a less smooth texture and provides a less cooling sensation during application, compared to the composition of comparative example 3, while the composition of inventive example 5 is comparable to the composition of comparative example 3 in terms of skin finish and application.

[0198] A less smooth texture allows the composition of the inventive example to more easily retain its shape and provide a unique appearance.

Claims

Claims

1. Composition for caring for keratinous materials, comprising, relative to the total weight of the composition: i. from 0.01% by weight to 3% by weight of neohesperidin dihydrochalcone; ii. from 0.01% by weight to 10% by weight of at least one C-glycoside selected from C-[3-D-xylopyranoside-2-hydroxypropane or CaD -xylopyranoside-2-hydroxypropane, and combinations thereof; iii. from 0.01% by weight to 3% by weight of at least one carnosine compound selected from carnosine, L-carnosine, D-carnosine, D / L-carnosine, carnosine, carnosine HCl salt, anserine, D-anserine, L-anserine, L-anserine HNO3 salt and combinations thereof; iv. from 0.01% by weight to 3% by weight of Leontopodium alpinum callus culture extract; (v) from 0.01% by weight to 3% by weight of the extract of tuber aestivum; and (vi) from 0.01% by weight to 3% by weight of Salvia miltiorrhiza leaf extract.

2. Composition according to claim 1, further comprising, relative to the total weight of the composition: from 0.01% by weight to 10% by weight, preferably from 0.1% by weight to 5% by weight, more preferably from 0.5% by weight to 3% by weight of cetyl alcohol; from 0.01% by weight to 5% by weight, preferably from 0.1% by weight to 2.5% by weight, more preferably from 0.5% by weight to 2% by weight of glyceryl stearate; from 0.01% by weight to 5% by weight, preferably from 0.1% by weight to 2.5% by weight, more preferably from 0.5% by weight to 2% by weight of PEG-100 stearate; from 0.1% by weight to 20% by weight, preferably from 0.5% by weight to 15% by weight, preferably from 1% by weight to 10% by weight of shea butter; 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 1% by weight of tetrasodium glutamate diacetate; and from 0.01% by weight to 5% by weight, preferably from 0.1% by weight to 4% by weight, more preferably from 0.4% by weight to 2% by weight of acrylamide / sodium acryloyldimethyltaurate copolymer.

3. Non-therapeutic method for caring for keratinous materials, comprising applying the composition according to any one of claims 1 to 2 to the keratinous materials.