WO2024065763A1 - Composition for caring for keratin materials - Google Patents

Composition for caring for keratin materials Download PDF

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Publication number
WO2024065763A1
WO2024065763A1 PCT/CN2022/123490 CN2022123490W WO2024065763A1 WO 2024065763 A1 WO2024065763 A1 WO 2024065763A1 CN 2022123490 W CN2022123490 W CN 2022123490W WO 2024065763 A1 WO2024065763 A1 WO 2024065763A1
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WO
WIPO (PCT)
Prior art keywords
composition
hydroxypropane
carnosine
extract
composition according
Prior art date
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PCT/CN2022/123490
Other languages
French (fr)
Inventor
Wanze WANG
Shanshan ZANG
Xinxin Chen
Mei Zhang
Yici ZHAO
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L'oreal
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Priority to PCT/CN2022/123490 priority Critical patent/WO2024065763A1/en
Priority to FR2211941A priority patent/FR3140266A1/en
Publication of WO2024065763A1 publication Critical patent/WO2024065763A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9728—Fungi, e.g. yeasts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/592—Mixtures of compounds complementing their respective functions
    • A61K2800/5922—At least two compounds being classified in the same subclass of A61K8/18

Definitions

  • the present invention relates to a cosmetic composition.
  • the present invention relates to a composition for caring for keratin materials.
  • the present invention also relates to a non-therapeutic method for caring for keratin materials.
  • the skin is the protective barrier for the human body. It protects the interior of the body from physical injury (such as trauma) and biological injury (such as bacteria, viruses or fungi) .
  • compositions providing skin barrier repairing and anti-aging effect.
  • the present invention provides a composition for caring for keratin materials, comprising:
  • -R represents a saturated C 1 to C 10 , in particular C 1 to C 4 , alkyl radical which can optionally be substituted by at least one radical selected from OH, COOH or COOR” 2 , with R” 2 being a saturated C 1 -C 4 alkyl radical,
  • -S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units, in particular up to 6 sugar units, in pyranose and/or furanose form and of the L and/or D series, it being possible for the said monosaccharide or polysaccharide to be substituted by a hydroxyl group which is necessarily free and optionally one or more optionally protected amine functional group (s) , and
  • -X represents a radical selected from the–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 ) -radical and more particularly a–CH (OH) -radical,
  • the S-CH 2 -X bond represents a bond of C-anomeric nature, which can be ⁇ or ⁇ ,
  • composition of the present invention shows significant better in anti-aging relevant attribute such as skin firmness improvement and shows much lower transdermal water loss which represent better skin barrier function.
  • the present invention provides a non-therapeutic method for caring for keratin materials, comprising applying the composition according to the first aspect of the present invention to the keratin materials.
  • Fig. 1 shows sensory profiles of compositions of invention example 5 and comparative example 3, wherein the solid line stands for composition of invention example 5, and the dotted line stands for composition of comparative example 3.
  • keratin materials is intended to cover human skin, mucous membranes such as the lips. Facial skin is most particularly considered according to the present invention.
  • the present invention provides a composition for caring for keratin materials, comprising:
  • composition of the present invention comprises Neohesperidin dihydrochalcone.
  • Neohesperidin dihydrochalcone is a polyphenol of natural oxygen with a large antioxidant potential over a very broad spectrum of several species of radicals, which is capable of acting on three cellular targets: membrane, nucleus and cytoplasm.
  • Neohesperidin dihydrochalcone is part of the dihydrochalcones family, which is part of the flavonoids class.
  • Neohesperidin DHC is a glycosylated flavonoid which has the following structure:
  • Neohesperidin DHC (CAS number 20702-77-6) may especially be obtained either from neohesperidin which may 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.
  • Synthesis from naringin is based on the conversion thereof to give phloroacetophenone-4'- ⁇ -neohesperidoside, which may be condensed with isovanillin (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) .
  • Neohesperidin dihydrochalcone is especially available under the commercial reference Neohesperidin DC from HEALTHTECH BIOACTIVES (FERRER) .
  • Neohesperidin dihydrochalcone may exist in the hydrate form.
  • neohesperidin dihydrochalcone is present in an amount ranging from 0.01 wt. %to 10 wt. %, preferably from 0.01 wt. %to 5 wt. %, and more preferably from 0.01 wt. %to 3 wt. %, relative to the total weight of the composition.
  • composition of the present invention comprises at least one C-glycoside selected from compounds of formula (I) :
  • -R represents a saturated C 1 to C 10 , in particular C 1 to C 4 , alkyl radical which can optionally be substituted by at least one radical selected from OH, COOH or COOR” 2 , with R” 2 being a saturated C 1 -C 4 alkyl radical,
  • -S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units, in particular up to 6 sugar units, in pyranose and/or furanose form and of the L and/or D series, it being possible for the said monosaccharide or polysaccharide to be substituted by a hydroxyl group which is necessarily free and optionally one or more optionally protected amine functional group (s) , and
  • -X represents a radical selected from the–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 ) -radical and more particularly a–CH (OH) -radical,
  • the S-CH2-X bond represents a bond of C-anomeric nature, which can be ⁇ or ⁇ , and also their physiologically acceptable salts, their solvates, such as the hydrates, and their optical and geometrical isomers.
  • the C-glycoside of use for the implementation of the invention are in particular those for which R denotes a saturated linear C 1 to C 6 , in particular C 1 to C 4 , preferentially C 1 to C 2 , alkyl radical and more preferably a methyl radical.
  • a monosaccharide of the invention can be selected from D-glucose, D-galactose, D-mannose, D-xylose, D-lyxose or L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D-glucosamine or N-acetyl-D-galactosamine and advantageously denotes D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose and in particular D-xylose.
  • a polysaccharide of the invention comprising up to 6 sugar units can be selected from D-maltose, D-lactose, D-cellobiose, D-maltotriose, a disaccharide combining a uronic acid selected from D-iduronic acid or D-glucuronic acid with 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 can advantageously be selected from xylobiose, methyl- ⁇ -xylobioside, xylotriose, xylotetraose, xylopentaose and xylohexaose and in particular xylobiose, which is composed of two xylose molecules linked via a 1-4 bond.
  • S can represent a monosaccharide selected from D-glucose, D-xylose, L-fucose, D-galactose or D-maltose and in particular D-xylose.
  • -R denotes an unsubstituted linear C 1 -C 4 , in particular C 1 -C 2 , alkyl radical, especially a methyl radical;
  • -S represents a monosaccharide as described above and selected in particular from D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, and in particular 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 comprise conventional non-toxic salts of the said compounds, such as those formed from organic or inorganic acids. Mention may be made, by way of example, of the salts of inorganic acids, such as sulfuric acid, hydrochloric acid. Mention may also be made of the salts of organic acids, which can comprise one or more carboxylic, sulfonic or phosphonic acid groups. Mention may in particular be made of propionic acid, acetic acid, terephthalic acid, citric acid and tartaric acid.
  • neutralization of the acid group (s) can be carried out with an inorganic base, such as LiOH, NaOH, KOH, Ca (OH) 2 , NH 4 OH, Mg (OH) 2 or Zn (OH) 2 , or with an organic base, such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine.
  • an inorganic base such as LiOH, NaOH, KOH, Ca (OH) 2 , NH 4 OH, Mg (OH) 2 or Zn (OH) 2
  • organic base such as a primary, secondary or tertiary alkylamine, for example triethylamine or butylamine.
  • This primary, secondary or tertiary alkylamine can comprise one or more nitrogen and/or oxygen atoms and can thus comprise, for example, one or more alcohol 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.
  • solvates which are acceptable for the compounds described in the present invention comprise conventional solvates, such as those formed during the final stage of preparation of the said compounds due to the presence of solvents. Mention may be made, by way of example, of the solvates due to the presence of water or of linear or branched alcohols, such as ethanol or isopropanol.
  • a C-glycoside corresponding to the formula (I) can be used alone or as a mixture with other C-glycoside and in any proportion.
  • a C-glycoside which is suitable for the invention can in particular be obtained by the synthetic method described in the document WO 02/051828.
  • C- ⁇ -D-xylopyranoside-2-hydroxypropane or C- ⁇ -D-xylopyranoside-2-hydroxypropane and better still C- ⁇ -D-xylopyranoside-2-hydroxypropane can advantageously be used for the preparation of a composition according to the invention.
  • the C-glycoside can be C- ⁇ -D-xylopyranoside-2-hydroxypropane (or hydroxypropyl tetrahydropyrantriol) provided in the form of a solution containing 70%by weight of active material in water and propylene glycol.
  • the C-glycoside is present in the composition in an amount ranging from 0.01 wt. %to 25%, preferably from 0.01 wt. %to 15 wt. %, and more preferably from 0.01 wt. %to 10 wt. %, relative to the total weight of the composition.
  • the composition of the present invention comprises at least one carnosine compound.
  • the carnosine compound is selected from compounds of formula (II)
  • R1 represents H or CH3 and R2 represents H or COOH, or salts thereof.
  • salts of compounds of formula (II) are preferably salts of compounds of formula (II) with mineral acids, particularly salts of formula (III) :
  • n 1, 2 or 3 and A represents HCl or HNO 3 and R1 represents H or CH 3 and R2 represents H or COOH.
  • carnosine compounds useful for the composition according to the present invention are known and are accessible by conventional processes of organic chemistry.
  • 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 HNO 3 salt, and combinations thereof.
  • the carnosine compound is present in an amount ranging from 0.01 wt. %to 10 wt. %, preferably from 0.01 wt. %to 5 wt. %, more preferably from 0.01 wt.%to 3 wt. %, relative to the total weight of the composition.
  • the composition according to the present invention comprises an anti-redness active ingredient.
  • anti-redness active ingredients mention can be made to 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.
  • 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 t
  • the compositon 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.
  • 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 glycyr
  • the composition of the present invention comprises leontopodium alpinum extract, in particular, leontopodium alpinum callus culture extract, as anti-redness active ingredient.
  • the anti-redness active ingredient is present in the composition in an amount ranging from 0.01 wt. %to 10%, preferably from 0.01 wt. %to 5 wt. %, and more preferably from 0.01 wt. %to 3 wt. %, relative to the total weight of the composition.
  • the composition of the present invention comprises a truffle extract.
  • Truffle is the common name given to the edible fruiting body of an ectomycorrhizal ascomyscetes fungus which takes a more or less globular form. The fungus may produce several truffles.
  • the truffle (s) which may be used within the context of the invention are preferentially truffles of the genus Tuber, of the Tuberaceae family, in the Pezizales order. There are more than a hundred species thereof. Among the latter, mention may especially be made of black (Périgord) truffle (Tuber melanosporum) , white (Piedmont) truffle (Tuber magnatum) , white (summer) truffle (Tuber aestivum) , winter truffle (Tuber Brumale) , bianchetto truffle (Tuber borchii) , or else Chinese truffles (Tuber sinensis and Tuber indicum) .
  • the truffle (s) used within the context of the invention are selected from white truffles and black truffles.
  • the truffle (s) used within the context of the invention are black (Périgord) truffle (Tuber melanosporum) , white (summer) truffle (Tuber aestivum) , or a mixture of the two.
  • the truffle extract (s) may especially be obtained from an extraction solvent by using an extraction technique selected from the extraction techniques well known from the prior art.
  • the extraction solvent is chosen from water, water-soluble or water-miscible solvents (hydrophilic solvents) , and mixtures thereof.
  • hydrophilic solvents mention may especially be made of substantially linear or branched lower monoalcohols having 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 derivatives thereof; and mixtures thereof.
  • substantially linear or branched lower monoalcohols having 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 derivatives thereof; and mixtures thereof.
  • the truffle extract is said to be aqueous.
  • the truffle extract is said to be alcoholic.
  • the truffle extract is said to be glycolic.
  • the extract is said to be aqueous-alcoholic.
  • the extract is said to be aqueous-glycolic.
  • the truffle extract (s) are obtained from an extraction solvent comprising water.
  • the truffle extract (s) are then aqueous, aqueous-alcoholic or aqueous-glycolic.
  • the truffle extract (s) are aqueous or aqueous-glycolic.
  • the truffle extract is present in the composition in an amount ranging from 0.01 wt. %to 10%, preferably from 0.01 wt. %to 5 wt. %, and more preferably from 0.01 wt. %to 3 wt. %, relative to the total weight of the composition.
  • the composition according to the present invention comprises a Salvia miltiorrhiza extract.
  • the Salvia miltiorrhiza extract comprises a lot of 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%.
  • composition of the present invention comprises Salvia miltiorrhiza extract, in particular, Salvia miltiorrhiza leaf extract.
  • the Salvia miltiorrhiza extract is present in the composition in an amount ranging from 0.01 wt. %to 10%, preferably from 0.01 wt. %to 5 wt. %, and more preferably from 0.01 wt. %to 3 wt. %, relative to the total weight of the composition.
  • composition of the present invention may comprise an aqueous phase.
  • Said aqueous phase comprises water.
  • the aqueous phase comprises an organic solvent miscible with water (at room temperature 25°C) selected from glycols and polyols having from 2 to 20 carbon atoms, preferably from 2 to 10 carbon atoms, and preferentially having 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.
  • an organic solvent miscible with water selected from glycols and polyols having from 2 to 20 carbon atoms, preferably from 2 to 10 carbon atoms, and preferentially having 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
  • the organic solvent miscible with water selected from glycols and polyols is present in the composition in an amount ranging from 0.5 wt. %to 20 wt. %, preferably from 1 wt. %to 10 wt. %, relative to the total weight of the composition.
  • the aqueous phase of the composition of the present invention comprises water and glycerin.
  • aqueous phase is present in the composition of the present invention in an amount ranging from 70 wt. %to 99.8 wt. %, relative to the total weight of the composition.
  • composition of the present invention may comprise a fatty phase.
  • the fatty phase preferably contains at least one oil, notably a cosmetic oil. It may also contain other fatty substances.
  • oil means a water-immiscible non-aqueous compound that is liquid at room temperature (20°C) and at atmospheric pressure (760 mmHg) .
  • the oils may be volatile or non-volatile.
  • non-volatile refers to an oil whose vapour pressure at room temperature and atmospheric pressure is non-zero and is less than 10 -3 mmHg (0.13 Pa) .
  • volatile oil means any oil that is capable of evaporating on contact with the skin in less than one hour, at room temperature and atmospheric pressure.
  • a fatty phase that is suitable for preparing the compositions, notably cosmetic compositions, accordingto the invention may comprise hydrocarbon-based oils, silicone oils, fluoro oils or non-fluoro oils, or mixtures thereof.
  • They may be of animal, plant, mineral or synthetic origin.
  • silicon oil means an oil comprising at least one silicon atom, and notably at least one Si-O group.
  • fluoro oil means an oil comprising at least one fluorine atom.
  • hydrocarbon-basedoil means an oil mainly containing hydrogen and carbon atoms.
  • the oils may optionally comprise oxygen, nitrogen, sulfur and/or phosphorus atoms, for example in the form of hydroxyl or acid radicals.
  • the fatty phase is present in the composition of the present invention in an amount ranging from 1 wt. %to 20 wt. %, preferably from 2 wt. %to 10 wt. %, relative to the total weight of the composition of the present invention.
  • composition of the present invention may comprise one or more additional cosmetic active ingredient in addition to cosmetic active ingredients mentioned above.
  • vitamins such as vitamin A (retinol) , vitamin E (tocopherol) , vitamin C (ascorbic acid) , vitamin B5 (panthenol) , vitamin B3 (niacinamide) , and derivatives of said vitamins (in particular esters) and mixtures thereof; urea; caffeine; salicylic acid and derivatives thereof; alpha-hydroxyacids such as lactic acid or glycolic acid and derivatives thereof; sunscreens; extracts from algae, fungi, yeasts and bacteria; enzymes; other moisturing agents such as hydroxyethyl urea, agents acting on the microcirculation, and mixtures thereof.
  • composition of the present invention may also comprise conventional cosmetic adjuvants or additives, for instance fragrances, preserving agents (for example, chlorphenesin and phenoxyethanol) and bactericides, surfactants, pH regulators (for example citric acid) , thickeners such as xanthan gum and acrylamide/sodium acryloyldimethyltaurate copolymer, and mixtures thereof.
  • fragrances for instance, preserving agents (for example, chlorphenesin and phenoxyethanol) and bactericides, surfactants, pH regulators (for example citric acid) , thickeners such as xanthan gum and acrylamide/sodium acryloyldimethyltaurate copolymer, and mixtures thereof.
  • preserving agents for example, chlorphenesin and phenoxyethanol
  • bactericides for example, bactericides, surfactants, pH regulators (for example citric acid)
  • pH regulators for example citric acid
  • thickeners such as xant
  • composition according to the present invention further comprises, relative to the total weight of the composition:
  • composition can provide a less smooth texture, which makes it easier for the composition of invention example to keep its shape and deliver a unique appearance.
  • the present invention provides a composition for caring for keratin materials comprising, relative to the total weight of the composition:
  • carnosine compound selected from carnosine, L-carnosine, D-carnosine, D/L-carnosine, carnicine, carnicine HCl salt, anserine, D-anserine, L-anserine, L-anserine HNO 3 salt, and combinations thereof;
  • composition of the present invention may be in the form of gel, cream, or lotion.
  • composition of the present invention can be used for caring for keratin materials, for example, the human skin, especially facial skin or the skin around eyes.
  • the present invention provides a non-therapeutic method for caring for keratin materials, comprising applying the composition according to the first aspect of the present invention to the keratin materials.
  • compositions of invention examples (IE. ) 1-5 and comparative examples (CE. ) 1-3 were prepared according to the amounts given in Tables 2 and 3. The amount of each component is given in%by weight of the total weight of the composition containing it.
  • composition of invention examples 1-5 are compositions according to the present invention.
  • Composition of comparative example 1 does not comprise neohesperidin dihydrochalcone.
  • Composition of comparative examples 2-3 do not comprise neohesperidin dihydrochalcone and a carnosine compound.
  • compositions listed above were prepared as follows, taking the composition of invention example 5 as an example:
  • compositions of invention examples (IE. ) 1-4 and comparative examples (CE. ) 1-2 were evaluated in terms of skin barrier function through trans epidermal water loss (TEWL) and anti-aging effect through skin firmness and length of wrinkles.
  • TEWL trans epidermal water loss
  • TEWL Trans epidermal water loss
  • compositions to be evaluated were evenly applied on the test area–inner forearm under at 2.0 mg/cm 2 in a room at 20-22°C with a relative humidity of40%-50%.
  • Trans epidermal water loss was measured with a vapometer at T 0 (the time just before applyingthe test compositions) and T 1h (1 hour after applyingthe test compositions) .
  • increase rate ofTrans Epidermal Water Loss (TEWL) at T 1h as compared with T 0 was used to evaluate the effect for improving skin barrier function of the test compositions.
  • compositions were invited to use compositions to be tested for 4 weeks and evaluated the compositions in terms of skin firmness by dermatologists.
  • compositions of invention examples 1-3 deliver better skin barrier function and anti-aging effect.
  • compositions of invention example 5 and comparative example 3 were evaluated by a trained expert panel in random for 37 attributes. Results were presented in the form of sensory profiles accompanied by their mean data. Threshold for significant difference in the test is fixed at 5%and 10%.
  • composition of invention example 5 shows less smooth texture and delivers less cooling feel during application, as compared with composition of comparative example 3, while composition of invention example 5 is comparable to composition of comparative example 3 in terms of skin finish and application.
  • composition of invention example to keep its shape and deliver a unique appearance.

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Abstract

A composition for caring keratin materials comprises: (i) neohesperidin dihydrochalcone; (ii) at least one C-glycoside; and (iii) at least one carnosine compound. A non-therapeutic method for caring for keratin materials comprises applying said composition to the keratin materials.

Description

COMPOSITION FOR CARING FOR KERATIN MATERIALS TECHNICAL FIELD
The present invention relates to a cosmetic composition. In particular, the present invention relates to a composition for caring for keratin materials. The present invention also relates to a non-therapeutic method for caring for keratin materials.
BACKGROUND ART
The skin is the protective barrier for the human body. It protects the interior of the body from physical injury (such as trauma) and biological injury (such as bacteria, viruses or fungi) .
The development of formulations dedicated to caring for the skin is permanent.
It is also known to use active ingredients in the cosmetic products for treating or caring for the skin, such as cleaning, hydration, providing skin-barrier, anti-aging, pore minimizing, and so on. Among them, providing skin-barrier and anti-aging are always interests to consumers around the world.
However, there is no such cosmetic product which can effectively provide skin barrier repairing and anti-aging effect.
It is desired to have cosmetic products, which can provide skin barrier repairing and anti-aging effect.
SUMMARY OF THE INVENTION
The inventors have now discovered that it is possible to formulate compositions providing skin barrier repairing and anti-aging effect.
Accordingly, in a first aspect, the present invention provides a composition for caring for keratin materials, comprising:
(i) neohesperidin dihydrochalcone;
(ii) at least one C-glycoside selected from compounds of formula (I) :
Figure PCTCN2022123490-appb-000001
in which:
-R represents a saturated C 1 to C 10, in particular C 1 to C 4, alkyl radical which can optionally be substituted by at least one radical selected from OH, COOH or COOR”  2, with R” 2 being a saturated C 1-C 4 alkyl radical,
-S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units, in particular up to 6 sugar units, in pyranose and/or furanose form and of the L and/or D series, it being possible for the said monosaccharide or polysaccharide to be substituted by a hydroxyl group which is necessarily free and optionally one or more optionally protected amine functional group (s) , and
-X represents a radical selected from the–CO-, -CH (OH) -, -CH (NH 2) -, -CH (NHCH 2CH 2CH 2OH) -, -CH (NHPh) -and–CH (CH 3) -groups and in particular a–CO-, -CH (OH) -or–CH (NH 2) -radical and more particularly a–CH (OH) -radical,
the S-CH 2-X bond represents a bond of C-anomeric nature, which can beαorβ,
and also their physiologically acceptable salts, their solvates, such as the hydrates, and their optical and geometrical isomers; and
(iii) at least one carnosine compound.
The inventors found that the composition of the present invention shows significant better in anti-aging relevant attribute such as skin firmness improvement and shows much lower transdermal water loss which represent better skin barrier function.
In a second aspect, the present invention provides a non-therapeutic method for caring for keratin materials, comprising applying the composition according to the first aspect of the present invention to the keratin materials.
Other advantages of the present invention will emerge more clearly on reading the description and the examples that follow.
BRIEF DESCRIPTION OF THE DRAWINGS
Implementations of the present invention will now be described, by way of example only, with reference to the attached figure, wherein:
Fig. 1 shows sensory profiles of compositions of invention example 5 and comparative example 3, wherein the solid line stands for composition of invention example 5, and the dotted line stands for composition of comparative example 3.
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 the present invention belongs to. When the definition of a term in the present description conflicts with the meaning as commonly understood by those skilled in the art the present invention belongs to, the definition described herein shall apply.
In that which follows and unless otherwise indicated, the limits of a range of values are included within this range, in particular in the expressions "between... and…" and "from. . . to... " .
Moreover, the expression "at least one" used in the present description is equivalent to the expression "one or more" .
Throughout the instant application, the term “comprising” is to be interpreted as encompassing all specifically mentioned features as well as optional, additional, unspecified ones. As used herein, the use of the term “comprising” also discloses the embodiment wherein no features other than the specifically mentioned features are present (i.e. “consisting of” ) .
Unless otherwise specified, all numerical values expressing amount of ingredients and the like which are used in the description and claims are to be understood as being modified by the term “about” . Accordingly, unless indicated to the contrary, the numerical values and parameters described herein are approximate values which are capable of being changed according to the desired purpose as required.
For the purposes of the present invention, the term “keratin materials” is intended to cover human skin, mucous membranes such as the lips. Facial skin is most particularly considered according to the present invention.
All percentages in the present invention refer to weight percentage, unless otherwise specified.
According to the first aspect, the present invention provides a composition for caring for keratin materials, comprising:
(i) neohesperidin dihydrochalcone;
(ii) at least one C-glycoside; and
(iii) at least one carnosine compound.
Neohesperidin dihydrochalcone
According to the first aspect, the composition of the present invention comprises Neohesperidin dihydrochalcone.
Neohesperidin dihydrochalcone (DHC) is a polyphenol of natural oxygen with a large antioxidant potential over a very broad spectrum of several species of radicals, which is capable of acting on three cellular targets: membrane, nucleus and cytoplasm.
Neohesperidin dihydrochalcone (DHC) is part of the dihydrochalcones family, which is part of the flavonoids class. Neohesperidin DHC is a glycosylated flavonoid which has the following structure:
Figure PCTCN2022123490-appb-000002
It is also known under its IUPAC name: 1- (4- ( (2-O- [6-Deoxy-α-L-mannopyranosyl] -β-D-glucopyranosyl) oxy) -2, 6-dihydroxyphenyl) -3- [3-hydroxy-4-methoxyphenyl] -1-propanone.
Neohesperidin DHC (CAS number 20702-77-6) may especially be obtained either from neohesperidin which may 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. Synthesis from naringin is based on the conversion thereof to give phloroacetophenone-4'-β-neohesperidoside, which may be condensed with isovanillin (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) .
Neohesperidin dihydrochalcone is especially available under the commercial reference Neohesperidin DC from HEALTHTECH BIOACTIVES (FERRER) .
Neohesperidin dihydrochalcone may exist in the hydrate form.
Advantageously, neohesperidin dihydrochalcone is present in an amount ranging from 0.01 wt. %to 10 wt. %, preferably from 0.01 wt. %to 5 wt. %, and more preferably from 0.01 wt. %to 3 wt. %, relative to the total weight of the composition.
C-glycosides
According to the first aspect, the composition of the present invention comprises at least one C-glycoside selected from compounds of formula (I) :
Figure PCTCN2022123490-appb-000003
in which:
-R represents a saturated C 1 to C 10, in particular C 1 to C 4, alkyl radical which can optionally be substituted by at least one radical selected from OH, COOH or COOR”  2, with R” 2 being a saturated C 1-C 4 alkyl radical,
-S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units, in particular up to 6 sugar units, in pyranose and/or furanose form and of the L and/or D series, it being possible for the said monosaccharide or polysaccharide to be substituted by a hydroxyl group which is necessarily free and optionally one or more optionally protected amine functional group (s) , and
-X represents a radical selected from the–CO-, -CH (OH) -, -CH (NH 2) -, -CH (NHCH 2CH 2CH 2OH) -, -CH (NHPh) -and–CH (CH 3) -groups and in particular a–CO-, -CH (OH) -or–CH (NH 2) -radical and more particularly a–CH (OH) -radical,
the S-CH2-X bond represents a bond of C-anomeric nature, which can beαorβ, and also their physiologically acceptable salts, their solvates, such as the hydrates, and their optical and geometrical isomers.
The C-glycoside of use for the implementation of the invention are in particular those for which R denotes a saturated linear C 1 to C 6, in particular C 1 to C 4, preferentially C 1 to C 2, alkyl radical and more preferably a methyl radical.
Mention may in particular be made, among the alkyl groups suitable for the implementation of the invention, of the methyl, ethyl, isopropyl, n-propyl, n-butyl, t-butyl, isobutyl, sec-butyl, pentyl, n-hexyl, cyclopropyl, cyclopentyl or cyclohexyl groups.
According to one embodiment of the invention, use may be made of a C-glycoside corresponding to the formula (I) for which S can represent a monosaccharide or a polysaccharide comprising up to 6 sugar units, in pyranose and/or furanose form and of L and/or D series, the said mono-or polysaccharide exhibiting at least one necessarily free hydroxyl functional group and/or optionally one or more necessarily protected amine functional groups, X and R otherwise retaining all of the definitions given above.
Advantageously, a monosaccharide of the invention can be selected from D-glucose, D-galactose, D-mannose, D-xylose, D-lyxose or L-fucose, L-arabinose, L-rhamnose, D-glucuronic acid, D-galacturonic acid, D-iduronic acid, N-acetyl-D-glucosamine or N-acetyl-D-galactosamine and advantageously denotes D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose and in particular D-xylose.
More particularly, a polysaccharide of the invention comprising up to 6 sugar units can be selected from D-maltose, D-lactose, D-cellobiose, D-maltotriose, a disaccharide combining a uronic acid selected from D-iduronic acid or D-glucuronic acid with 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 can advantageously be selected from xylobiose, methyl-β-xylobioside, xylotriose, xylotetraose, xylopentaose and xylohexaose and in particular xylobiose, which is composed of two xylose molecules linked via a 1-4 bond.
More particularly, S can represent a monosaccharide selected from D-glucose, D-xylose, L-fucose, D-galactose or D-maltose and in particular D-xylose.
Preferably, use is made of a C-glycoside of formula (I) for which:
-R denotes an unsubstituted linear C 1-C 4, in particular C 1-C 2, alkyl radical, especially a methyl radical;
-S represents a monosaccharide as described above and selected in particular from D-glucose, D-xylose, N-acetyl-D-glucosamine or L-fucose, and in particular 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 comprise conventional non-toxic salts of the said compounds, such as those formed from organic or inorganic acids. Mention may be made, by way of example, of the salts of inorganic acids, such as sulfuric acid, hydrochloric acid. Mention may also be made of the salts of organic acids, which can comprise one or more carboxylic, sulfonic or phosphonic acid groups. Mention may in particular be made of propionic acid, acetic acid, terephthalic acid, citric acid and tartaric acid.
When the compound of formula (I) comprises an acid group, neutralization of the acid group (s) can be carried out with an inorganic base, such as LiOH, NaOH, KOH, Ca (OH)  2, NH 4OH, 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 can comprise one or more nitrogen and/or oxygen atoms and can thus comprise, for example, one or more alcohol 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.
The solvates which are acceptable for the compounds described in the present invention comprise conventional solvates, such as those formed during the final stage of preparation of the said compounds due to the presence of solvents. Mention may be made, by way of example, of the solvates due to the presence of water or of linear or branched alcohols, such as ethanol or isopropanol.
Of course, according to the invention, a C-glycoside corresponding to the formula (I) can be used alone or as a mixture with other C-glycoside and in any proportion.
A C-glycoside which is suitable for the invention can in particular be obtained by the synthetic method described in the document WO 02/051828.
Mention may in particular be made, by way of non-limiting illustration of the C-glycoside compounds which are particularly suitable for the invention, of the following compounds:
-C-β-D-xylopyranoside-n-propane-2-one,
-C-α-D-xylopyranoside-n-propan-2-one,
-C-β-D-xylopyranoside-2-hydroxypropane,
-C-α-D-xylopyranoside-2-hydroxypropane,
-1- (C-β-D-fucopyranoside) propan-2-one,
-1- (C-α-D-fucopyranoside) propan-2-one,
-1- (C-β-L-fucopyranoside) propan-2-one,
-1- (C-α-L-fucopyranoside) propan-2-one,
-1- (C-β-D-fucopyranoside) -2-hydroxypropane,
-1- (C-α-D-fucopyranoside) -2-hydroxypropane,
-1- (C-β-L-fucopyranoside) -2-hydroxypropane,
-1- (C-α-L-fucopyranoside) -2-hydroxypropane,
-1- (C-β-D-glucopyranosyl) -2-hydroxypropane,
-1- (C-α-D-glucopyranosyl) -2-hydroxypropane,
-1- (C-β-D-galactopyranosyl) -2-hydroxypropane,
-1- (C-α-D-galactopyranosyl) -2-hydroxypropane,
-1- (C-β-D-fucofuranosyl) propan-2-one,
-1- (C-α-D-fucofuranosyl) propan-2-one,
-1- (C-β-L-fucofuranosyl) propan-2-one,
-1- (C-α-L-fucofuranosyl) propan-2-one,
-C-β-D-maltopyranoside-n-propane-2-one,
-C-α-D-maltopyranoside-n-propan-2-one,
-C-β-D-maltopyranoside-2-hydroxypropane,
-C-α-D-maltopyranoside-2-hydroxypropane, their isomers and their mixtures.
According to one embodiment, C-β-D-xylopyranoside-2-hydroxypropane or C-α-D-xylopyranoside-2-hydroxypropane and better still C-β-D-xylopyranoside-2-hydroxypropane can advantageously be used for the preparation of a composition according to the invention.
According to a specific embodiment, the C-glycoside can be C-β-D-xylopyranoside-2-hydroxypropane (or hydroxypropyl tetrahydropyrantriol) provided in the form of a solution containing 70%by weight of active material in water and propylene glycol.
Advantageously, the C-glycoside is present in the composition in an amount ranging from 0.01 wt. %to 25%, preferably from 0.01 wt. %to 15 wt. %, and more preferably from 0.01 wt. %to 10 wt. %, relative to the total weight of the composition.
Carnosine compounds
According to the first aspect, the composition of the present invention comprises at least one carnosine compound.
Preferably, the carnosine compound is selected from compounds of formula (II)
Figure PCTCN2022123490-appb-000004
wherein R1 represents H or CH3 and R2 represents H or COOH, or salts thereof.
According to the present invention, salts of compounds of formula (II) are preferably salts of compounds of formula (II) with mineral acids, particularly salts of formula (III) :
Figure PCTCN2022123490-appb-000005
wherein n represents 1, 2 or 3 and A represents HCl or HNO 3 and R1 represents H or CH 3 and R2 represents H or COOH.
The carnosine compounds useful for the composition according to the present invention are known and are accessible by conventional processes of organic chemistry.
More 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 HNO 3 salt, and combinations thereof.
As commercial product for carnosine, mention can be made to that available under the tradename
Figure PCTCN2022123490-appb-000006
P.N. 844033 from Symrise.
Advantageously, the carnosine compound is present in an amount ranging from 0.01 wt. %to 10 wt. %, preferably from 0.01 wt. %to 5 wt. %, more preferably from 0.01 wt.%to 3 wt. %, relative to the total weight of the composition.
Unexpectedly, the inventors have found that the combination of neohesperidin dihydrochalcone, C-glycoside and carnosine compound results in significant synergy effect on skin barrier repairing and anti-aging effect.
Anti-redness active ingredients
Preferably, the composition according to the present invention comprises an anti-redness active ingredient.
As examples of anti-redness active ingredients, mention can be made to 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.
In some embodiments, the compositon 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.
In some embodiments, the composition of the present invention comprises leontopodium alpinum extract, in particular, leontopodium alpinum callus culture extract, as anti-redness active ingredient.
If presents, advantageously, the anti-redness active ingredient is present in the composition in an amount ranging from 0.01 wt. %to 10%, preferably from 0.01 wt. %to 5 wt. %, and more preferably from 0.01 wt. %to 3 wt. %, relative to the total weight of the composition.
Truffle extracts
Preferably, the composition of the present invention comprises a truffle extract.
Truffle is the common name given to the edible fruiting body of an ectomycorrhizal ascomyscetes fungus which takes a more or less globular form. The fungus may produce several truffles.
The truffle (s) which may be used within the context of the invention are preferentially truffles of the genus Tuber, of the Tuberaceae family, in the Pezizales order. There are more than a hundred species thereof. Among the latter, mention may especially be made of black (Périgord) truffle (Tuber melanosporum) , white (Piedmont) truffle (Tuber magnatum) , white (summer) truffle (Tuber aestivum) , winter truffle (Tuber Brumale) , bianchetto truffle (Tuber borchii) , or else Chinese truffles (Tuber sinensis and Tuber indicum) .
According to one particular embodiment, the truffle (s) used within the context of the invention are selected from white truffles and black truffles. According to a preferred embodiment, the truffle (s) used within the context of the invention are black (Périgord) truffle (Tuber melanosporum) , white (summer) truffle (Tuber aestivum) , or a mixture of the two.
Within the context of the invention, the truffle extract (s) may especially be obtained from an extraction solvent by using an extraction technique selected from the extraction techniques well known from the prior art.
Generally, the extraction solvent is chosen from water, water-soluble or water-miscible solvents (hydrophilic solvents) , and mixtures thereof.
Among the hydrophilic solvents, mention may especially be made of substantially linear or branched lower monoalcohols having 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 derivatives thereof; and mixtures thereof.
When the extraction solvent is water, the truffle extract is said to be aqueous.
When the extraction solvent is a substantially linear or branched lower monoalcohol having from 1 to 8 carbon atoms, the truffle extract is said to be alcoholic.
When the extraction solvent is a polyol, the truffle extract is said to be glycolic.
When the extraction solvent is a mixture of water and of one or more substantially linear or branched lower monoalcohols having from 1 to 8 carbon atoms, the extract is said to be aqueous-alcoholic.
When the extraction solvent is a mixture of water and of one or more polyols, the extract is said to be aqueous-glycolic.
Within 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.
If presents, advantageously, the truffle extract is present in the composition in an amount ranging from 0.01 wt. %to 10%, preferably from 0.01 wt. %to 5 wt. %, and more preferably from 0.01 wt. %to 3 wt. %, relative to the total weight of the composition.
Salvia miltiorrhiza extracts
Preferably, the composition according to the present invention comprises a Salvia miltiorrhiza extract.
Various extracts of Salvia miltiorrhiza have obvious antibacterial and anti-inflammatory effects. In addition extracts of Salvia miltiorrhiza have anti-oxidiant and anti-aging effect.
The Salvia miltiorrhiza extract comprises a lot of 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%.
In some embodiments, the composition of the present invention comprises Salvia miltiorrhiza extract, in particular, Salvia miltiorrhiza leaf extract.
If presents, advantageously, the Salvia miltiorrhiza extract is present in the composition in an amount ranging from 0.01 wt. %to 10%, preferably from 0.01 wt. %to 5 wt. %, and more preferably from 0.01 wt. %to 3 wt. %, relative to the total weight of the composition.
Aqueous phase
The composition of the present invention may comprise an aqueous phase.
Said aqueous phase comprises water.
Preferably, the aqueous phase comprises an organic solvent miscible with water (at room temperature 25℃) selected from glycols and polyols having from 2 to 20 carbon atoms, preferably from 2 to 10 carbon atoms, and preferentially having 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.
If presents, advantageously, the organic solvent miscible with water selected from glycols and polyols is present in the composition in an amount ranging from 0.5 wt. %to  20 wt. %, preferably from 1 wt. %to 10 wt. %, relative to the total weight of the composition.
Preferably, the aqueous phase of the composition of the present invention comprises water and glycerin.
If presents, advantageously, aqueous phase is present in the composition of the present invention in an amount ranging from 70 wt. %to 99.8 wt. %, relative to the total weight of the composition.
Fatty phase
The composition of the present invention may comprise a fatty phase.
The fatty phase preferably contains at least one oil, notably a cosmetic oil. It may also contain otherfatty substances.
The term “oil” means a water-immiscible non-aqueous compound that is liquid at room temperature (20℃) and at atmospheric pressure (760 mmHg) .
The oils may be volatile or non-volatile.
The term “non-volatile” refers to an oil whose vapour pressure at room temperature and atmospheric pressure is non-zero and is less than 10 -3 mmHg (0.13 Pa) .
For the purposes of the invention, the term "volatile oil" means any oil that is capable of evaporating on contact with the skin in less than one hour, at room temperature and atmospheric pressure.
A fatty phase that is suitable for preparing the compositions, notably cosmetic compositions, accordingto the invention may comprise hydrocarbon-based oils, silicone oils, fluoro oils or non-fluoro oils, or mixtures thereof.
They may be of animal, plant, mineral or synthetic origin.
For the purposes of the present invention, the term “silicone oil” means an oil comprising at least one silicon atom, and notably at least one Si-O group.
The term "fluoro oil" means an oil comprising at least one fluorine atom.
The term "hydrocarbon-basedoil" means an oil mainly containing hydrogen and carbon atoms.
The oils may optionally comprise oxygen, nitrogen, sulfur and/or phosphorus atoms, for example in the form of hydroxyl or acid radicals.
If presents, advantageously, the fatty phase is present in the composition of the present invention in an amount ranging from 1 wt. %to 20 wt. %, preferably from 2 wt. %to 10 wt. %, relative to the total weight of the composition of the present invention.
Additional cosmetic active ingredients
The composition of the present invention may comprise one or more additional cosmetic active ingredient in addition to cosmetic active ingredients mentioned above.
As examples of cosmetic active ingredient, mention can be made of vitamins such as vitamin A (retinol) , vitamin E (tocopherol) , vitamin C (ascorbic acid) , vitamin B5 (panthenol) , vitamin B3 (niacinamide) , and derivatives of said vitamins (in particular esters) and mixtures thereof; urea; caffeine; salicylic acid and derivatives thereof; alpha-hydroxyacids such as lactic acid or glycolic acid and derivatives thereof; sunscreens; extracts from algae, fungi, yeasts and bacteria; enzymes; other moisturing agents such as hydroxyethyl urea, agents acting on the microcirculation, and mixtures thereof.
It is easy for the skilled in the art to adjust the amount of the additional cosmetic active ingredient based on the final use of the composition according to the present invention.
Additional adjuvants or additives
The composition of the present invention may also comprise conventional cosmetic adjuvants or additives, for instance fragrances, preserving agents (for example, chlorphenesin and phenoxyethanol) and bactericides, surfactants, pH regulators (for example citric acid) , thickeners such as xanthan gum and acrylamide/sodium acryloyldimethyltaurate copolymer, and mixtures thereof.
The skilled in the art can select the amount of the additional adjuvants or additive so as not to adversely impact the final use of the composition according to the present invention.
In some preferred embodiments, the composition according to the present invention further comprises, relative to the total weight of the composition:
from 0.01 wt. %to 10 wt. %, preferably from 0.1 wt. %to 5 wt. %, more preferably from 0.5 wt. %to 3 wt. %of cetyl alcohol;
from 0.01 wt. %to 5 wt. %, preferably from 0.1 wt. %to 2.5 wt. %, more preferably from 0.5 wt. %to 2 wt. %of glyceryl stearate;
from 0.01 wt. %to 5 wt. %, preferably from 0.1 wt. %to 2.5 wt. %, more preferably from 0.5 wt. %to 2 wt. %of PEG-100 stearate;
from 0.1 wt. %to 20 wt. %, preferably from 0.5 wt. %to 15 wt. %, more preferably from 1 wt. %to 10 wt. %of shea butter;
from 0.01 wt. %to 10 wt. %, preferably from 0.05 wt. %to 5 wt. %, more preferably from 0.1 wt. %to 1 wt. %of tetrasodium glutamate diacetate; and
from 0.01 wt. %to 5 wt. %, preferably from 0.1 wt. %to 4 wt. %, more preferably from 0.4 wt. %to 2 wt. %of acrylamide/sodium acryloyldimethyltaurate copolymer.
Such composition can provide a less smooth texture, which makes it easier for the composition of invention example to keep its shape and deliver a unique appearance.
According to a particularly preferred embodiment, the present invention provides a composition for caring for keratin materials comprising, relative to the total weight of the composition:
(i) from 0.01 wt. %to 3 wt. %of neohesperidin dihydrochalcone;
(ii) from 0.01 wt. %to 10 wt. %of at least one C-glycoside selected from C-β-D-xylopyranoside-2-hydroxypropane or C-α-D-xylopyranoside-2-hydroxypropane, and combinations thereof;
(iii) from 0.01 wt. %to 3 wt. %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 HNO 3 salt, and combinations thereof;
(iv) from 0.01 wt. %to 3 wt. %of leontopodium alpinum callus culture extract;
(iv) from 0.01 wt. %to 3 wt. %of tuber aestivum extract; and
(v) from 0.01 wt. %to 3 wt. %of Salvia miltiorrhiza leaf extract.
Galenic form and method
The composition of the present invention may be in the form of gel, cream, or lotion.
The composition of the present invention can be used for caring for keratin materials, for example, the human skin, especially facial skin or the skin around eyes.
According to the second aspect, the present invention provides a non-therapeutic method for caring for keratin materials, comprising applying the composition according to the first aspect of the present invention to the keratin materials.
The following examples serve to illustrate the present invention without, however, being limiting in nature.
EXAMPLES
Main raw materials used, trade names and supplier thereof are listed in Table 1.
Table 1
Figure PCTCN2022123490-appb-000007
Figure PCTCN2022123490-appb-000008
Invention examples 1-5 and comparative examples 1-3
Compositions of invention examples (IE. ) 1-5 and comparative examples (CE. ) 1-3 were prepared according to the amounts given in Tables 2 and 3. The amount of each component is given in%by weight of the total weight of the composition containing it.
Table 2
Figure PCTCN2022123490-appb-000009
Table 3
Figure PCTCN2022123490-appb-000010
Composition of invention examples 1-5 are compositions according to the present invention.
Composition of comparative example 1 does not comprise neohesperidin dihydrochalcone.
Composition of comparative examples 2-3 do not comprise neohesperidin dihydrochalcone and a carnosine compound.
Preparation process:
The compositions listed above were prepared as follows, taking the composition of invention example 5 as an example:
1) . adding water, glycerin, chlorphenesin, xanthan gum, and tetrasodium glutamate diacetate into a main vessel with stirring at 65℃ to obtain an uniform mixture;
2) . premixing Cetyl Alcohol, GLYCERYL STEARATE (and) PEG-100 STEARATE, Butyrospermum Parkii (Shea) Butter in another container with stirring at 65℃ to obtain an uniform oil phase; and transferring the oil phase into the main vessel with stirring to obtain an uniform combination;
3) . cooling the uniform combination to below 40℃;
4) . premixing hydroxypropyl tetrahydropyrantriol, carnosine, neohesperidin dihydrochalcone, leontopodium alpinum callus culture extract, tuber aestivum extract, and salvia miltiorrhiza leaf extract into a mixture;
5) adding the mixture obtained in 4) into the main vessel below 40℃ with stirring,
6) adding Acrylamide/sodium acryloyldimethyltaurate copolymer (and) isohexadecane (and) polysorbate 80 into the main vessel below 40℃ with stirring to obtain a homogeneous composition.
Evaluation
Compositions of invention examples (IE. ) 1-4 and comparative examples (CE. ) 1-2 were evaluated in terms of skin barrier function through trans epidermal water loss (TEWL) and anti-aging effect through skin firmness and length of wrinkles.
Trans epidermal water loss (TEWL)
33 females of 30-55 years old were invited to complete the test. Compositions to be evaluated were evenly applied on the test area–inner forearm under at 2.0 mg/cm 2 in a room at 20-22℃ with a relative humidity of40%-50%.
Trans epidermal water loss (TEWL) was measured with a vapometer at T 0 (the time just before applyingthe test compositions) and T 1h (1 hour after applyingthe test compositions) . According to the method of single use oftest compositions, increase rate ofTrans Epidermal Water Loss (TEWL) at T 1h as compared with T 0was used to evaluate the effect for improving skin barrier function of the test compositions.
Skin firmness
63 females of 30-55 years old were invited to use compositions to be tested for 4 weeks and evaluated the compositions in terms of skin firmness by dermatologists.
Length of wrinkles
67 females of 30-55 years old were invited to use compositions to be tested for 2 weeks and the lengths ofwrinkles (Crow’s feet) were measured via Primos 3D at T 0 (the time just before applying the test compositions) and T 2W (2 weeks after applying the test compositions) . The decrease rate of the length of wrinkles at T 2w as compared with T 0was calculated.
The results on trans epidermal water loss (TEWL) , skin firmness and length of wrinkles were summarized in Table 4 below.
Table 4
Figure PCTCN2022123490-appb-000011
It can be seen from Table 4 that as compared with compositions of comparative examples 1-2, compositions of invention examples 1-3 deliver better skin barrier function and anti-aging effect.
Texture
Compositions of invention example 5 and comparative example 3 were evaluated by a trained expert panel in random for 37 attributes. Results were presented in the form of sensory profiles accompanied by their mean data. Threshold for significant difference in the test is fixed at 5%and 10%.
Sensory profiles of compositions of invention example 5 and comparative example 3 were shown in Fig. 1, wherein the solid line stands for composition of invention example 5, and the dotted line stands for composition of comparative example 3.
It can be seen from Fig. 1 that composition of invention example 5 shows less smooth texture and delivers less cooling feel during application, as compared with composition of comparative example 3, while composition of invention example 5 is comparable to composition of comparative example 3 in terms of skin finish and application.
Such less smooth texture makes it easier for the composition of invention example to keep its shape and deliver a unique appearance.

Claims (16)

  1. A composition for caring for keratin materials, comprising:
    (i) neohesperidin dihydrochalcone;
    (ii) at least one C-glycoside selected from compounds of formula (I) :
    Figure PCTCN2022123490-appb-100001
    in which:
    - R represents a saturated C 1 to C 10, in particular C 1 to C 4, alkyl radical which can optionally be substituted by at least one radical selected from OH, COOH or COOR”  2, with R” 2 being a saturated C 1-C 4 alkyl radical,
    - S represents a monosaccharide or a polysaccharide comprising up to 20 sugar units, in particular up to 6 sugar units, in pyranose and/or furanose form and of the L and/or D series, it being possible for the said monosaccharide or polysaccharide to be substituted by a hydroxyl group which is necessarily free and optionally one or more optionally protected amine functional group (s) , and
    - X represents a radical selected from the –CO-, -CH (OH) -, -CH (NH 2) -, -CH (NHCH 2CH 2CH 2OH) -, -CH (NHPh) -and–CH (CH 3) -groups and in particular a–CO-, -CH (OH) -or–CH (NH 2) -radical and more particularly a–CH (OH) -radical,
    the S-CH 2-X bond represents a bond of C-anomeric nature, which can be α or β,
    and also their physiologically acceptable salts, their solvates, such as the hydrates, and their optical and geometrical isomers; and
    (iii) at least one carnosine compound.
  2. Composition according to claim 1, wherein neohesperidin dihydrochalcone is present in an amount ranging from 0.01 wt. %to 10 wt. %, preferably from 0.01 wt. %to 5 wt. %, and more preferably from 0.01 wt. %to 3 wt. %, relative to the total weight of the composition.
  3. Composition according to claim 1 or 2, wherein the C-glycoside is selected from
    -C-β-D-xylopyranoside-n-propane-2-one,
    -C-α-D-xylopyranoside-n-propan-2-one,
    -C-β-D-xylopyranoside-2-hydroxypropane,
    -C-α-D-xylopyranoside-2-hydroxypropane,
    -1- (C-β-D-fucopyranoside) propan-2-one,
    -1- (C-α-D-fucopyranoside) propan-2-one,
    -1- (C-β-L-fucopyranoside) propan-2-one,
    -1- (C-α-L-fucopyranoside) propan-2-one,
    -1- (C-β-D-fucopyranoside) -2-hydroxypropane,
    -1- (C-α-D-fucopyranoside) -2-hydroxypropane,
    -1- (C-β-L-fucopyranoside) -2-hydroxypropane,
    -1- (C-α-L-fucopyranoside) -2-hydroxypropane,
    -1- (C-β-D-glucopyranosyl) -2-hydroxypropane,
    -1- (C-α-D-glucopyranosyl) -2-hydroxypropane,
    -1- (C-β-D-galactopyranosyl) -2-hydroxypropane,
    -1- (C-α-D-galactopyranosyl) -2-hydroxypropane,
    -1- (C-β-D-fucofuranosyl) propan-2-one,
    -1- (C-α-D-fucofuranosyl) propan-2-one,
    -1- (C-β-L-fucofuranosyl) propan-2-one,
    -1- (C-α-L-fucofuranosyl) propan-2-one,
    -C-β-D-maltopyranoside-n-propane-2-one,
    -C-α-D-maltopyranoside-n-propan-2-one,
    -C-β-D-maltopyranoside-2-hydroxypropane,
    -C-α-D-maltopyranoside-2-hydroxypropane,
    their isomers and their mixtures.
  4. Composition according to any of claims 1 to 3, wherein the C-glycoside is present in an amount ranging from 0.01 wt. %to 25%, preferably from 0.01 wt. %to 15 wt. %, and more preferably from 0.01 wt. %to 10 wt. %, relative to the total weight of the composition.
  5. Composition according to any of claims 1 to 4, wherein the carnosine compound is selected from compounds of formula (II)
    Figure PCTCN2022123490-appb-100002
    wherein R1 represents H or CH 3 and R2 represents H or COOH,
    or salts thereof.
  6. Composition according to claim 5, wherein the carnosine compound is selected from the group consisting of carnosine, L-carnosine, D-carnosine, D/L-carnosine, carnicine, carnicine HCl salt, anserine, D-anserine, L-anserine, L-anserine HNO 3 salt, and combinations thereof.
  7. Composition according to any of claims 1 to 6, wherein the carnosine compound is present in an amount ranging from 0.01 wt. %to 10 wt. %, preferably from 0.01 wt. %to 5 wt. %, more preferably from 0.01 wt. %to 3 wt. %, relative to the total weight of the composition.
  8. Composition according to any of claims 1 to 7, further comprising an 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.
  9. Composition according to claim 8, wherein the anti-redness is present in an amount ranging from 0.01 wt. %to 10%, preferably from 0.01 wt. %to 5 wt. %, and more preferably from 0.01 wt. %to 3 wt. %, relative to the total weight of the composition.
  10. Composition according to any of claims 1 to 9, further comprising a truffle extract, wherein the truffle is selected from white truffles and black truffles such as  black (Périgord) truffle (Tuber melanosporum) , white (summer) truffle (Tuber aestivum) , and mixtures thereof.
  11. Composition according to claim 10, wherein the truffle extract is present in an amount ranging from 0.01 wt. %to 10%, preferably from 0.01 wt. %to 5 wt. %, and more preferably from 0.01 wt. %to 3 wt. %, relative to the total weight of the composition.
  12. Composition according to any of claims 1 to 11, further comprising a salvia miltiorrhiza extract.
  13. Composition according to claim 12, wherein the Salvia miltiorrhiza extract is present in the composition in an amount ranging from 0.01 wt. %to 10%, preferably from 0.01 wt. %to 5 wt. %, and more preferably from 0.01 wt. %to 3 wt. %, relative to the total weight of the composition.
  14. Composition according to claim 1, comprising, relative to the total weight of the composition:
    (i) from 0.01 wt. %to 3 wt. %of neohesperidin dihydrochalcone;
    (ii) from 0.01 wt. %to 10 wt. %of at least one C-glycoside selected from C-β-D-xylopyranoside-2-hydroxypropane or C-α-D-xylopyranoside-2-hydroxypropane, and combinations thereof;
    (iii) from 0.01 wt. %to 3 wt. %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 HNO 3 salt, and combinations thereof;
    (iv) from 0.01 wt. %to 3 wt. %of leontopodium alpinum callus culture extract;
    (iv) from 0.01 wt. %to 3 wt. %of tuber aestivum extract; and
    (v) from 0.01 wt. %to 3 wt. %of Salvia miltiorrhiza leaf extract.
  15. Composition according to any of claims 1 to 14, further comprising, relative to the total weight of the composition:
    from 0.01 wt. %to 10 wt. %, preferably from 0.1 wt. %to 5 wt. %, more preferably from 0.5 wt. %to 3 wt. %of cetyl alcohol;
    from 0.01 wt. %to 5 wt. %, preferably from 0.1 wt. %to 2.5 wt. %, more preferably from 0.5 wt. %to 2 wt. %of glyceryl stearate;
    from 0.01 wt. %to 5 wt. %, preferably from 0.1 wt. %to 2.5 wt. %, more preferably from 0.5 wt. %to 2 wt. %of PEG-100 stearate;
    from 0.1 wt. %to 20 wt. %, preferably from 0.5 wt. %to 15 wt. %, more preferably from 1 wt. %to 10 wt. %of shea butter;
    from 0.01 wt. %to 10 wt. %, preferably from 0.05 wt. %to 5 wt. %, more preferably from 0.1 wt. %to 1 wt. %of tetrasodium glutamate diacetate; and
    from 0.01 wt. %to 5 wt. %, preferably from 0.1 wt. %to 4 wt. %, more preferably from 0.4 wt. %to 2 wt. %of acrylamide/sodium acryloyldimethyltaurate copolymer.
  16. A non-therapeutic method for caring for keratin materials, comprising applying the composition according to any of claims 1 to 15 to the keratin materials.
PCT/CN2022/123490 2022-09-30 2022-09-30 Composition for caring for keratin materials WO2024065763A1 (en)

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FR2211941A FR3140266A1 (en) 2022-09-30 2022-11-17 COMPOSITION FOR CARE OF KERATINOUS MATERIALS

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