WO2024115359A1 - Composition comprenant un dérivé d'éthylzingerone en combinaison avec un dérivé d'acide spiculisporique - Google Patents

Composition comprenant un dérivé d'éthylzingerone en combinaison avec un dérivé d'acide spiculisporique Download PDF

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WO2024115359A1
WO2024115359A1 PCT/EP2023/083119 EP2023083119W WO2024115359A1 WO 2024115359 A1 WO2024115359 A1 WO 2024115359A1 EP 2023083119 W EP2023083119 W EP 2023083119W WO 2024115359 A1 WO2024115359 A1 WO 2024115359A1
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cosmetic composition
formula
compound
weight
composition according
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PCT/EP2023/083119
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English (en)
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Reda Agnaou
Géraldine Lerebour
Catherine Marion
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L'oreal
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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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0291—Micelles
    • 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
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/14—Preparations for removing make-up

Definitions

  • composition comprising an ethylzingerone derivative in combination with a spiculisporic acid derivative
  • the present invention relates to a composition, preferably antimicrobial, comprising at least one ethylzingerone derivative in combination with at least one derivative of the spiculisporic acid.
  • the present invention also relates to a cosmetic composition comprising, in a physiologically-acceptable medium, such a composition comprising at least one ethylzingerone derivative in combination with at least one derivative of the spiculisporic acid.
  • the present invention also relates to a method for preserving a cosmetic composition comprising the mixture of said cosmetic composition with such a composition comprising at least one ethylzingerone derivative in combination with at least one derivative of the spiculisporic acid.
  • Microorganisms can survive and propagate in cosmetic, pharmaceutical and food products free of preservatives.
  • Antimicrobial agents also called preservative agents or preservatives
  • preservatives are inactivated by a variety of surfactants.
  • micellar solutions that have both an optimum microbiological protection and a good ocular tolerance, while guaranteeing an effective makeup removal. Furthermore, these micellar solutions should be stable over time, and/or develop no odor or bad odor over time.
  • compositions according to the invention are particularly well-suited for use in micellar solutions.
  • the compositions according to the invention allow providing micellar solutions having both an optimum microbiological protection while guaranteeing an effective makeup removal.
  • the micellar solutions according to the invention remain stable even after several weeks at room temperature, and even at temperatures above 25°C (for example at 37°C and 45°C), and do not feature any change in odor and/or any visual change over time (apparition of a trouble, for example).
  • an object of the present invention is a composition, preferably an antimicrobial composition, comprising:
  • R1 represents a (C1-C4) alkyl group such as methyl or ethyl, preferably ethyl;
  • R2 represents a hydrogen atom or a (C1-C4) alkyl group such as methyl or ethyl, preferably R2 represents a hydrogen atom;
  • - R3 represents a linear (Ci-C 6 ) alkyl group, a branched (C 3 -C 6 ) alkyl group or a linear (C 2 - Ce) alkenyl group or a branched (Cs-Ce) alkenyl group;
  • R’ represents an aliphatic chain, linear or branched, cyclic or acyclic, saturated or unsaturated, comprising from 1 to 16 carbon atom(s), and M + , when present, represents a cationic counterion, in particular an alkaline metal such as sodium and potassium, an alkaline-earth metal such as calcium, or the ammonium ion.
  • said composition is antimicrobial also so-called “preferably antimicrobial composition”.
  • Another object of the present invention is a cosmetic composition, preferably for the skin and/or the hair, preferably a makeup remover composition, comprising a composition according to the invention, in a physiologically-acceptable medium.
  • Another object of the invention is the use i) of at least one compound (I) combined with ii) at least one compound (II) and/or (II’) as an antimicrobial agent, in particular on the seeds Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Enterococcus faecalis, Candida albicans and Aspergillus niger, in particular on the strain Aspergilus niger.
  • Another object of the present invention is a method for preserving a cosmetic composition, in particular comprising a physiologically-acceptable medium, comprising the mixture of said cosmetic composition with a composition according to the invention.
  • an object of the invention is also a method for preserving a cosmetic formulation, in particular comprising a physiologically-acceptable medium, comprising the mixture of said cosmetic formulation with a composition according to the invention.
  • Another object of the present invention is a method for non-therapeutic cosmetic treatment, in particular for care and/or makeup and/or cleaning of keratin materials, comprising applying a cosmetic composition according to the invention on said keratin materials.
  • the preferably antimicrobial composition and the cosmetic composition according to the invention comprise one or more compound(s) of formula (I) as defined before and/or any one of its salts, and/or any one of its solvates.
  • R1 represents a methyl or ethyl radical
  • R2 represents a hydrogen atom or a methyl or ethyl radical
  • R3 represents a linear (Ci-Ce) alkyl
  • the compounds of formula (I) are such that, when considered together or separately (preferably when considered together):
  • R1 represents a methyl or ethyl radical, preferably ethyl
  • R2 represents a hydrogen atom or a methyl or ethyl radical, preferably a hydrogen atom
  • R3 represents a linear (Ci-Ce) alkyl, preferably a methyl
  • the compound(s) of formula (I) are 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and/or any one of salts thereof, and/or any one of solvates thereof.
  • 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one may be in a solvated, in particular hydrated, form.
  • 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one may be in a form salified by an organic or mineral base and have the following formula (la’): [Chem 5] wherein M + represents a cationic counterion, in particular an alkaline metal such as sodium and potassium, an alkaline-earth metal such as calcium, or the ammonium ion. ii) Compound of formula (II) and/or (II’)
  • the antimicrobial composition, preferably antimicrobial, and the cosmetic composition according to the invention comprise one or more compound(s) of formula (II) and/or (II’) as defined before, and/or any one of its stereoisomers, and/or any one of its salts, and/or any one of its solvates such as its hydrates.
  • R’ represents an aliphatic chain, linear or branched, cyclic or acyclic, saturated or unsaturated, comprising from 2 to 14 carbon atoms, preferably from 3 to 12 carbon atoms, more preferably from 5 to 10 carbon atoms, advantageously 9 carbon atoms.
  • the aliphatic chain is acyclic.
  • the aliphatic chain is linear.
  • the aliphatic chain is saturated.
  • the salts of the compounds of formula (II) are organic or mineral base salts.
  • the salts of the compounds of formula (II) are salts of alkaline metals such as sodium or potassium, salts of alkaline-earth metals, such as calcium, or salts of ammonium ions, preferably salts of sodium ions.
  • the salts of the compounds of formula (II) are selected from among the salts of the following formula as well as their stereoisomers:
  • M + represents a cationic counterion, in particular an alkaline metal such as sodium and potassium, an alkaline-earth metal such as calcium, or the ammonium ion.
  • the preferably antimicrobial composition and the cosmetic composition according to the invention comprise one or more compound(s) of formula (II’) as defined before as well as their stereoisomers, their salts and solvates such as hydrates.
  • the salts of the compounds of formula (II’) are salts of sodium ions.
  • the compound(s) of formula (II) are present in the composition, preferably antimicrobial, according to the invention in the form of a salt, in particular a sodium salt, a monosodium or disodium salt.
  • the composition, preferably antimicrobial, and the cosmetic composition according to the invention preferably comprise a compound of formula (II).
  • the compound of formula (II) is spiculisporic acid, also known as 4,5- dicarboxy-4-pentadecanolide, as well as its stereoisomers, its salts, and its solvates such as hydrates.
  • the spiculisporic acid has the following formula (ll-d) :
  • the preferably antimicrobial composition and/or the cosmetic composition according to the invention have a weight ratio between the weight content of the compound(s) of formula (II) and/or (II’) as defined before, in particular of formula (II), and the weight content of the compound(s) of formula (I) as defined before, in particular 4- (3-ethoxy-4-hydroxyphenyl)butan-2-one, comprised between 0.1 and 10, preferably between 0.2 and 5, preferably between 0.5 and 3, preferably between 0.8 and 2, preferably between 1 and 1 .5.
  • the cosmetic composition according to the invention comprises, in a physiolog ically- acceptable medium, The preferably antimicrobial composition according to the invention.
  • the compound(s) of formula (I) as defined before, in particular 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one are present at a concentration comprised between 0.01% and 2% by weight with respect to the total weight of the cosmetic composition, preferably between 0.01 % and 1.5%, preferably between 0.02% and 1% by weight, preferably between 0.05% and 0.8%, advantageously between 0.08% and 0.7%, even more advantageously between 0.3% and 0.7%.
  • the compound(s) of formula (II) and (II’), in particular of formula (II) such as of formula (ll-d) are present at a concentration comprised between 0.01% and 2% by weight with respect to the total weight of the cosmetic composition, preferably between 0.02% and 0.1 % by weight, preferably between 0.05% and 0.8%, advantageously between 0.1% and 0.7%, even more advantageously between 0.3% and 0.7%.
  • the cosmetic composition according to the invention comprises a physiologically-acceptable medium.
  • physiologically-acceptable medium it should be understood a medium compatible with the skin, the mucosae and/or the dander.
  • the cosmetic composition according to the invention comprises an aqueous phase.
  • the aqueous phase contains water.
  • the used water may be sterile demineralized water and/or a floral water such as rose water, blueberry water, chamomile water or linden water, and/or natural thermal or mineral water, like for example: Vittel water, Vichy basin water, linage water, Roche Posay water, Bourboule water, Enghien-les-Bains water, Saint Gervais-les-Bains water, Neris-les- Bains water, Allevar-les-Bains water, Digne water, Maizieres water, Neyrac-les-Bains water, Lons-le-Saunier water, Bonnes water, Rochefort water, Saint Christau water, Fumades water and Tercis-les-Bains water, Avene water.
  • a floral water such as rose water, blueberry water, chamomile water or linden water
  • natural thermal or mineral water like for example: Vittel water, Vichy basin water, linage water, Roche Posay water, Bourboule water, Enghien-les-Bains water, Saint Gerva
  • the aqueous phase possibly contains at least one organic solvent soluble or miscible in water at 25°C.
  • the water soluble or miscible solvents suitable to the invention comprise (C2-C4) alkanols, linear or branched, such as ethanol and isopropanol, propanol, butanol; polyols having in particular from 2 to 20 carbon atoms, preferably from 2 to 6 carbon atoms, like, glycerol, diglycerol, propylene glycol, isoprene glycol, dipropylene glycol, butylene glycol, hexylene glycol, 1 ,3-propanediol, pentylene glycol, polyethylene glycols having from 2 to 200 ethylene oxide units, and mixtures thereof.
  • C2-C4 alkanols linear or branched, such as ethanol and isopropanol, propanol, butanol
  • polyols having in particular from 2 to 20 carbon atoms, preferably from 2 to 6 carbon atoms, like, glycerol, diglycerol, propylene glycol
  • the amount of water soluble or miscible solvents preferably ranges from 0.01 % to 15% by weight, preferably from 1 % to 10% by weight, still better from2% to 8% by weight, still better from 3% from 5% by weight with respect to the total weight of the cosmetic composition.
  • the aqueous phase represents from 15% to 97% by weight, preferably from 30% to 90% by weight, still better from 45% to 90% by weight with respect to the total weight of the cosmetic composition.
  • the aqueous phase represents 100% by weight of the cosmetic composition, for example when the cometic composition is a micellar solution or a micellar jelly.
  • the cosmetic composition of the invention is micellar, i.e. in a form with a micellar structure, preferably with a spherical micellar structure.
  • the micelles may be direct or inverted, preferably direct.
  • the cosmetic composition further comprises iii) one or more surfactant(s) different from the compounds of formula (II) and (IP).
  • the surfactant(s) iii) of the invention may be selected from among nonionic, anionic, zwitterionic or amphoteric surfactants.
  • the cosmetic composition comprises an amount of cationic surfactant lower than or equal to 1 .5% by weight with respect to the total weight of the cosmetic composition, preferably in an amount lower than or equal to 1 %, even more particularly lower than or equal to 0.5% by weight with respect to the total weight of the cosmetic composition, even more preferably the cosmetic composition comprises an amount lower than 0.5%, still better the cosmetic composition of the invention comprises no cationic surfactant.
  • the surfactant(s) is/are nonionic or anionic, preferably nonionic.
  • nonionic surfactant(s) mention may be made, alone or in mixtures, of a) fatty alcohols, b) alpha-diols, c) alkylphenols, these 3 types of compounds a) to c) being polyethoxylated, polypropoxylated and/or polyglycerolated, and having a fatty chain including for example 8 to 30 carbon atoms, in particular including 10 to 22 carbon atoms, the number of ethylene oxide or propylene oxide groups could range in particular from 2 to 200, in particular from 10 to 100 and the number of glycerol groups could range in particular from 2 to 200, in particular from 10 to 100.
  • EO ethylene oxide
  • PO propylene oxide
  • the nonionic surfactant(s) are selected from among: (poly)ethoxylated fatty alcohols; glycerolated fatty alcohols; alkylpolyglycosides, preferably oxyethylenated mono- and di-esters of fatty acids of sorbitan having from 2 to 200 mols of EO, in particular from 10 to 100 EO and alkylpolyglycosides like caprylyl/capryl glucoside.
  • the surfactant(s) are selected from among oxyethylenated mono- and di-esters of fatty acids of sorbitan having from 2 to 200 mols of EO, in particular from 10 to 100 EO such as propylene glycol stearate having from 10 to 30 EO such as 20 EO; glyceryl mono-distearate/polyethylene glycol stearate (100 EO).
  • fatty chain it should be understood a hydrocarbon chain comprising 6 to 30 carbon atoms, preferably from 8 to 24 carbon atoms, linear or branched, saturated or not, such as stearyl.
  • alkypolyglycosides these compounds may be represented by the following general formula: RiO-(R2O)t (G) v (III) wherein:
  • - Ri represents a linear or branched alkyl radical and/or alkenyl including about 8 to 24 carbon atoms, an alkylphenyl radical wherein the linear or branched alkyl radical includes from 8 to 24 carbon atoms;
  • R2 represents an alkylene radical including about 2 to 4 carbon atoms
  • - G represents a sugar unit including from 5 to 6 carbon atoms
  • - 1 denotes an integer inclusively comprised between 0 and 10, preferably between 0 and 4, preferably between 0 and 4;
  • Preferred alkyl polyglycosides according to the present invention are compounds of formula (III) wherein R1 represents more particularly a saturated or unsaturated, linear or branched alkyl radical including from 8 to 18 carbon atoms, t denotes a value ranging from 0 to 3 and still more particularly equal to 0, G may represent glucose, fructose or galactose, preferably glucose.
  • the degree of polymerization i.e. the value of v in the formula (III), may range from 1 to 15, preferably from 1 to 4.
  • the average degree of polymerization is more particularly comprised between 1 and 2 and even more preferably from 1 .1 to 1 .5.
  • glycosidic bonds between the sugar patterns are of the 1 -6 or 1 -4 type and preferably of the 1 -4 type.
  • Compounds of formula (III) are represented in particular by the products marketed by the company COGNIS under the brands PLANTAREN® (600 CS/ll, 1200 and 2000) or PLANTACARE® (818, 1200 and 2000). It is also possible to use the products marketed by the company SEPPIC under the brands TRITON CG 1 10 (or ORAMIX CG 1 10) and TRITON CG 312 (or ORAMIX® NS 10), the products marketed by the company B.A.S.F. under the brand LUTENSOL GD 70 or else those marketed by the company CHEM Y under the brand AGI O LK.
  • polyglucoside 1 ,4 Cs/C alkyl in an aqueous solution at 53% commercialized by COGNIS under the reference PLANTACARE® 818 UP.
  • mono or polyglycerolated surfactants these preferably include in average from 1 to 40 glycerol group(s), more particularly from 10 to 30 glycerol groups such as 20.
  • the surfactants are monoglycerolated or polyglycerolated and are preferably selected from among the compounds having the following formulas:
  • - R represents a saturated or unsaturated, linear or branched hydrocarbon radical, including from 8 to 40 carbon atoms and preferably from 10 to 30 carbon atoms;
  • R may possibly comprise heteroatoms such as oxygen and nitrogen.
  • R may possibly comprise one or more hydroxy and/or ether and/or amide group(s).
  • R represents C10-C20 alkyl and/or alkenyl radicals, possibly mono or polyhydroxylated.
  • the (poly)ethoxylated fatty alcohols are more particularly selected from among alcohols including from 8 to 30 carbon atoms, and preferably from 12 to 22 carbon atoms.
  • the (poly)ethoxylated fatty alcohols have one or more hydrocarbon group(s), linear or branched, saturated or unsaturated, comprising 8 to 30 carbon atoms, possibly substituted, in particular by one or more hydroxyl group(s) (in particular 1 to 4). If they are unsaturated, these compounds may comprise one to three carbon-carbon doublebonds, conjugated or not.
  • the (poly)ethoxylated fatty alcohol(s) meet(s) the following formula: R a -[O-CH 2 -CH 2 ] n -OH with
  • - R a representing a linear or branched C1-C40 alkyl group, a linear or branched C 2 - C30 alkenyl group (preferably C8-C30 alkyl); and - n represents an integer inclusively comprised between 1 and 200, preferably between 2 and 100, more particularly inclusively comprised between 10 and 50, even more particularly inclusively comprised between 15 and 30 such as 100 or 20.
  • the (poly)ethoxylated fatty alcohols are the fatty alcohols including from 8 to 22 carbon atoms and oxyethylenated by 1 to 30 mols of ethylene oxide (1 to 100 EO).
  • fatty alcohols including from 8 to 22 carbon atoms and oxyethylenated by 1 to 30 mols of ethylene oxide (1 to 100 EO).
  • the nonionic surfactants are polyglucoside C6-C24 alkyls and (poly)ethoxylated fatty alcohols and more particularly polyglucoside Cs-C alkyls.
  • the amount of nonionic surfactants ranges from 0.5% to 20% by weight, in particular from 1% to 10% by weight, and more particularly from 2 to 5% by weight with respect to the total weight of the cosmetic composition of the invention.
  • the cosmetic composition comprises one or more anionic surfactant agent(s).
  • anionic surfactant agent a surfactant including only anionic groups as ionic or ionizable groups.
  • anionic surfactant agents mention may be made of alkylcarboxylic acids, alkyl sulfates, alkyl ether sulfates, alkylamidoethersulfates, alkylarylpolyethersulfates, monoglyceride-sulfates, alkylsulfonates, alkylamidesulfonates, alkylarylsulfonates, alpha-olefin-sulfonates, paraffine-sulfonates, alkylsulfosuccinates, alkylethersulfosuccinates, alkylamide-sulfosuccinates, alkylsulfo-acetates, acylsarcosinates, acylglutamates, alkylglycinates, alkylsulfosuccinamates, acylisethionates and N-acyltau rates, the salts of alkyl monoesters and of polyglycoside
  • the salts of C6-C24 alkyl monoesters and of polyglycoside-polycarboxylic acids may be selected from among C6-C24 alkyl polyglycoside-citrates, C6-C24 alkyl polyglycosidetartrates and C6-C24 alkyl polyglycoside-sulfosuccinates.
  • anionic surfactant agent(s) When the anionic surfactant agent(s) is/are in the form of a salt, it/they may be selected from among alkaline metal salts such as sodium or potassium salts, and preferably sodium salts, ammonium salts, amine salts and in particular amino-alcohol salts or alkaline- earth metal salts such as magnesium salts.
  • alkaline metal salts such as sodium or potassium salts, and preferably sodium salts, ammonium salts, amine salts and in particular amino-alcohol salts or alkaline- earth metal salts such as magnesium salts.
  • amino-alcohol salts mention may be made in particular of mono-, di- or tri-ethanolammine salts, mono-, di- or tri-isopropanolamine salts, salts of 2-amino-2- methyl-1 -propanol, 2-amino-2-methyl-1 ,3-propanediol and tris(hydroxy-methyl)amino methane.
  • the salts of alkaline or alkaline-earth metals are used.
  • the alkyl (C6-C24) carboxylic acids in particular the alkyl (C10-C20) carboxylic acids, preferably derived from a natural source in particular a plant source such as stearic acid, are used, possibly in the form of salts of alkaline metals, of ammonium, of amino alcohols, and of alkaline-earth metals, or a mixture of these compounds; acylglutamates like disodium cocoyl glutamate; acylglycinates like sodium N-cocoyl glycinate.
  • amphoteric surfactant agents mention may be made of alkylbetains or alkyl amidopropyl betains, like coco-betain and cocamidopropyl betain.
  • the amount of anionic surfactants will preferably range from 0.5% to 20% by weight, in particular from 1 % to 10% by weight, and more particularly from 2% to 5% by weight with respect to the total weight of the cosmetic composition of the invention.
  • the amount of surfactants will preferably ranges from 0.5% to 30% by weight, in particular from 1 % to 20% by weight, and more particularly from 2% to 10% by weight, even more particularly from 3% to 8% by weight, more preferably between 4% and 6% with respect to the total weight of the cosmetic composition of the invention.
  • the cosmetic composition according to the invention may possibly comprise a hydrophilic, gelling agent, particulate or not, synthetic or derived from a natural source.
  • hydrophilic gelling agent As a hydrophilic gelling agent, mention may be made for example of carboxyvinyl polymers such as Carbopols (Carbomers) and Pemulen (acrylate/C10-C30-alkylacrylate copolymer); polyacrylamides like for example the crosslinked copolymers marketed under the brands Sepigel 305 (C.T.F.A. name: polyacrylamide/C13-14 isoparaffin/Laureth 7) or Simulgel 600 (C.T.F.A.
  • carboxyvinyl polymers such as Carbopols (Carbomers) and Pemulen (acrylate/C10-C30-alkylacrylate copolymer)
  • polyacrylamides like for example the crosslinked copolymers marketed under the brands Sepigel 305 (C.T.F.A. name: polyacrylamide/C13-14 isoparaffin/Laureth 7) or Simulgel 600 (C.T.F.A.
  • the hydrophilic gelling agent comprises at least xanthan gum.
  • the hydrophilic gelling agent is a mixture of one or more of the compounds listed hereinabove.
  • the hydrophilic gelling agent is selected from among xanthan gum, copolymers of acrylamide and sodium acryloyldimethyltaurate and any one of mixtures thereof.
  • the amount of gelling agent will preferably range from 0.01% to 30% by weight, preferably from 1 % to 15% by weight, still better from 2% to 7% by weight, still better from 3% to 5% by weight with respect to the total weight of the cosmetic composition of the invention.
  • the amount of gelling agent ranges from 0.1% to 0.5% by weight with respect to the total weight of the cosmetic composition of the invention.
  • the cosmetic composition according to the invention is a micellar solution, a micellar jelly or a micellar two-phase composition.
  • a micellar solution is a single-phase aqueous solution comprising an aqueous phase and at least one surfactant.
  • micellar jelly is a gelled single-phase aqueous solution, i.e. comprising an aqueous phase, at least one surfactant, and iv) at least one gelling agent as defined hereinabove.
  • the cosmetic composition according to the invention is a micellar two-phase composition.
  • a micellar two-phase composition comprises an aqueous phase, at least one surfactant, and v) one or more fatty substance(s).
  • fatty substance an organic compound that is insoluble in water at ordinary room temperature (25°C) and at the atmospheric pressure (760 mm Hg) (a solubility lower than 5% and preferably lower than 1% and even more preferably lower than 0.1%). They have in their structure at least one hydrocarbon including at least 6 carbon atoms or a series of at least two siloxane groups. Furthermore, fatty substances are generally soluble in organic solvents under the same conditions of temperature and pressure, like for example chloroform, ethanol, benzene, jelly oil or decamethylcyclopentasiloxane.
  • the fatty substance(s) of the invention are derived from a natural or synthetic source, preferably natural, more preferably from a plant source. They are different from fatty acids because salified fatty acids form soaps that are generally soluble in aqueous media.
  • the cosmetic composition contains one or more fatty substance(s) v) which consist of hydrocarbon liquid fatty substances at 25°C and at the atmospheric pressure.
  • the hydrocarbon liquid fatty substance(s) are selected from among Ce-Ci6 hydrocarbons or with more than 16 carbon atoms up to 60 carbon atoms, preferably between C& and C16, and in particular alkanes, animal oils, vegetable oils, glycerides or synthetic fluorinated oils, fatty alcohols, fatty acid and/or fatty alcohol esters, silicones.
  • the liquid fatty substance(s) are selected from among non-silicone oils.
  • the cosmetic composition comprises at least one hydrocarbon liquid fatty substance selected from among:
  • oils formed by esters of fatty acids and polyols, in particular triglycerides, such as sunflower oil, sesame oil or rapeseed oil, macadamia, soybean oil, sweet almond oil, calophyllum oil, palm oil, grapeseed oil, corn oil, arara oil, cotton oil, apricot oil, avocado oil, jojoba oil, olive oil, coconut oil or cereal germ oil;
  • triglycerides such as sunflower oil, sesame oil or rapeseed oil, macadamia, soybean oil, sweet almond oil, calophyllum oil, palm oil, grapeseed oil, corn oil, arara oil, cotton oil, apricot oil, avocado oil, jojoba oil, olive oil, coconut oil or cereal germ oil;
  • esters of formula R d -C(O)-O-R e wherein R d represents the rest of a higher fatty acid including from 7 to 19 carbon atoms and R e represents a hydrocarbon chain including from 3 to 20 carbon atoms, such as palmitates, adipates, myristates and benzoates, in particular diisopropyl adipate and isopropyl myristate; more preferably the esters of formula R d -C(O)-O-R e wherein R d represents the rest of a higher fatty acid including from 8 to 10 carbon atoms and R e represents a hydrocarbon chain including from 12 to 18 carbon atoms; - hydrocarbons and in particular linear, branched and/or cyclic, volatile or nonvolatile alkanes
  • aliphatic fatty monoalcohols having 6 to 30 carbon atoms, the hydrocarbon chain including no substitution group, such as oleic alcohol, decanol, dodecanol, octadecanol, octyldodecanol and linoleic alcohol;
  • the cosmetic composition comprises one or more fatty substance(s), in particular liquid at 25°C and at the atmospheric pressure, preferably one or more oil(s), at a concentration ranging from 0.01 to 90% by weight, with respect to the total weight of the composition, preferably ranging from 0.5 to 70% by weight, preferably ranging from 1 to 50% by weight, preferably ranging from 5 to 30% by weight.
  • the cosmetic composition according to the invention is substantially free of any cationic antimicrobial agent.
  • the cosmetic composition comprises less than 0.01% by weight with respect to the total weight of the cosmetic composition, preferably less than 0.005% by weight of a cationic antimicrobial agent.
  • the cosmetic composition according to the invention is completely free of any cationic antimicrobial agent.
  • cationic antimicrobial agent it should be understood for example the quaternary ammonium salts such as benzalkonium chloride, or biguanide.
  • the present invention also relates to a method for non-therapeutic cosmetic treatment of keratin materials, in particular for care and/or makeup and/or cleaning of keratin materials, preferably for removing makeup off keratin materials, comprising applying a cosmetic composition according to the invention on said keratin materials.
  • alkyl it should be understood a linear or branched hydrocarbon chain.
  • alkenyl it should be understood a linear or branched hydrocarbon chain, comprising one or more unsaturations, conjugated or not.
  • Example 1 Determination of the antimicrobial activity synergy
  • the culture medium is a Sabouraud broth supplemented with polyoxyethylene sorbitan monopalmitate (20 EO) (Tween 40 from Croda) and with Phytagel ⁇ BioReagent, at double concentration (namely a mixture of 5 g of Phytagel + 0.6 g of tween + 60 g of a Sabouraud broth).
  • polyoxyethylene sorbitan monopalmitate (20 EO) Teween 40 from Croda
  • Phytagel ⁇ BioReagent at double concentration (namely a mixture of 5 g of Phytagel + 0.6 g of tween + 60 g of a Sabouraud broth).
  • the incubation temperature of the microplate is 30°C +/- 1 °C under aerobic conditions.
  • the incubation duration of the microplate is 18h to 48h under aerobic conditions.
  • the tested product concentration range ultimately surrounds the value of the MIC of each product according to the principle: MIC/8, MIC/4, MIC/2, MIC and 2 MIC.
  • each of the obtained working solutions containing the compound A or B is added in the wells of the microplate.
  • 100 pL of a Sabouraud liquid nutritive broth seeded at double concentration with the Aspergillus niger strain and 50 pL of an aqueous solution at 1 %o by weight of agar are also added therein.
  • each of the obtained working solutions containing the compound A and 50 pL of each of the obtained working solutions containing the compound B are added in the wells of the microplate.
  • 100 pL of a Sabouraud liquid nutritive broth seeded at double concentration with the Aspergillus niger strain are also added therein.
  • This control corresponds to 100 pL of a sterile Sabouraud liquid nutritive broth seeded at double concentration, 50 pL of each of the obtained working solutions containing the compound A or B and 50 pL of an aqueous solution at 1 %o by weight of agar.
  • the microbial growth positive control corresponds to the mixture of 100 pL of an aqueous solution at 1 %o by weight of agar with 100 pL of a Sabouraud liquid nutritive broth seeded at double concentration with the Aspergillus niger strain in the absence of the compounds A and B.
  • the final volume present in each well of the microplate is 200 pL.
  • the antimicrobial efficiency improvement effect of the combination of A and B in particular of synergy of A and B has been carried out by calculating the synergy index (or FIC index), according to the following formula:
  • FIC Index (MIC of A with B/MIC of A) + (MIC of B with A/MIC of B) with:
  • the MIC is considered as the first concentration allowing obtaining a microbial growth percentage lower than or equal to 20%.
  • MIC of A with B and MIC of B with A are the respective concentrations of A and B in the combinations allowing obtaining a microbial growth percentage lower than or equal to 20%.
  • the growth percentage is calculated as follows:
  • results demonstrate a significant improvement (and possibly a synergistic effect since the FIC is lower than 0.75) in terms of antimicrobial activity of the combination of at least one compound of formula (I) such as 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and at least one compound of formula (II) and/or (II’) such as spiculisporic acid.
  • at least one compound of formula (I) such as 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one
  • at least one compound of formula (II) and/or (II’) such as spiculisporic acid.
  • no change in the odor of the formular or in the appearance of the composition of the invention comprising A and B has been noted, even after 2 months and at room temperature, at 45°C or at 4°C.
  • a makeup remover composition (micellar solution) has been prepared from the ingredients listed in the following table
  • Example 3 Micellar cosmetic compositions according to the invention
  • compositions have proven to be active on different microbial strains which effectively remove makeups on the face, the lips, the eyelids, the eyelashes and the eyebrows.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention se rapporte à une composition comprenant : (i) au moins un composé de formule (I) et/ou des sels de celui-ci, et/ou des solvates de celui-ci, dans lequel : - R1 représente un groupe alkyle en (C1-C4), tel que méthyle ou éthyle, de préférence éthyle ; - R2 représente un atome d'hydrogène ou un groupe alkyle en (C1-C4) tel que méthyle ou éthyle ; - R3 représente un groupe alkyle en(C1-C6) linéaire, un groupe alkyle en (C3-C6) ramifié ou un groupe alcényle en (C2-C6) linéaireou un groupe alcényle en (C3-C6) ramifié ; - X représente un groupe oxo = O ou hydroxyle OH ; et (ii) au moins un composé de formule (II) et/ou (II'), et/ou leurs stéréoisomères, et/ou leurs sels, et/ou leurs solvates : dans laquelle R' représente une chaîne aliphatique, linéaire ou ramifiée, cyclique ou acyclique, saturée ou insaturée, comprenant de 1 à 16 atomes de carbone, et M+, lorsqu'il est présent, représente un contre-ion cationique, en particulier un métal alcalin tel que le sodium et le potassium, un métal alcalino-terreux tel que le calcium, ou l'ion ammonium.
PCT/EP2023/083119 2022-11-28 2023-11-27 Composition comprenant un dérivé d'éthylzingerone en combinaison avec un dérivé d'acide spiculisporique WO2024115359A1 (fr)

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FR2212444A FR3142346A1 (fr) 2022-11-28 2022-11-28 Composition comprenant un dérivé d’éthylzingérone en combinaison avec un dérivé d’acide spiculisporique

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002047137A (ja) * 2000-07-27 2002-02-12 Shiyuu Uemura Keshohin:Kk ふき取り化粧料
WO2019002394A1 (fr) * 2017-06-30 2019-01-03 L'oreal Melange antimicrobien contenant du 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one et composition cosmetique le contenant
FR3075049A1 (fr) * 2017-12-19 2019-06-21 L'oreal Composition aqueuse moussante comprenant de l’acide spiculisporique, un alkyl polyglycoside et un polysaccharide

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002047137A (ja) * 2000-07-27 2002-02-12 Shiyuu Uemura Keshohin:Kk ふき取り化粧料
WO2019002394A1 (fr) * 2017-06-30 2019-01-03 L'oreal Melange antimicrobien contenant du 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one et composition cosmetique le contenant
FR3075049A1 (fr) * 2017-12-19 2019-06-21 L'oreal Composition aqueuse moussante comprenant de l’acide spiculisporique, un alkyl polyglycoside et un polysaccharide

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 200241, Derwent World Patents Index; AN 2002-376695, XP002809588 *
F.C. KULLP.C. EISMANH.D. SYLWESTROWKAR.L. MAYER, APPLIED MICROBIOLOGY, vol. 9, 1961, pages 538 - 541
G. SCHNEIDER ET AL.: "Ullmann's Encyclopedia of Industrial Chemistry", vol. 33, 2012, WILEY-VCH VERLAG GMBH & CO. KGAA, article "Skin Cosmetics", pages: 221
PABLO MIRALLES ET AL: "A Green and Rapid Analytical Method for the Determination of Hydroxyethoxyphenyl Butanone in Cosmetic Products by Liquid Chromatography", COSMETICS, vol. 5, no. 3, 16 July 2018 (2018-07-16), pages 44, XP055700417, DOI: 10.3390/cosmetics5030044 *

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