Composition comprising an ethylzingerone derivative in combination with a spiculisporic acid derivative

Abstract

Composition comprising an ethylzingerone derivative in combination with a spiculisporic acid derivative. The present invention relates to a composition comprising: (i) at least one compound of formula (I) and / or its salts, and / or its solvates, in which: - 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; - R3 represents a linear (C1-C6)alkyl group, a branched (C3-C6)alkyl group, or a linear (C2-C6)alkenyl group or a branched (C3-C6)alkenyl group; - X represents an oxo=O or hydroxyl group (OH);and (ii) at least one compound of formula (II) and / or (II'), and / or their stereoisomers, and / or their salts, and / or their solvates: wherein R' represents an aliphatic chain, linear or branched, cyclic or acyclic, saturated or unsaturated, comprising from 1 to 16 carbon atoms, and M+, when present, represents a cationic counterion, in particular an alkali metal such as sodium and potassium, an alkaline earth metal such as calcium, or the ammonium ion. Figure for the abstract: none;

Description

Title of the invention: Composition comprising an ethylzingerone derivative in combination with a spiculisporic acid derivative

[0001] The present invention relates to a composition, preferably antimicrobial, comprising at least one ethylzingerone derivative in combination with at least one spiculisporic acid derivative. 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 spiculisporic acid derivative. The present invention further relates to a method for preserving a cosmetic composition comprising mixing said cosmetic composition with such a composition comprising at least one ethylzingerone derivative in combination with at least one spiculisporic acid derivative.

[0002] Microorganisms can survive and multiply in cosmetic, pharmaceutical, and food products without preservatives. Antimicrobial agents (also called preservatives) are generally added to these preparations to prevent microbial growth over time.

[0003] Although every precaution is taken during the manufacture of these products, maintaining the microbial integrity of the products may require the presence of one or more preservatives compatible with the product and the stability of its composition. The products must not allow the growth or viability of contaminating microorganisms. Furthermore, maintaining cleanliness during use remains problematic, as the consumer's fingers, cosmetic applicators, or even the ambient air are not sterile. Preservatives are therefore necessary to reduce microbial contamination by consumers during normal use.

[0004] In addition, some commonly used preservatives are inactivated by a variety of surfactants. The more hydrophobic the preservative, the more it can be trapped in organized molecular systems such as micelles, and thus become less effective, or even ineffective, against microorganisms, especially pathogens (Ullmann's Encyclopedia of Industrial Chemistry, “Skin Cosmetics”, G. Schneider et al., vol. 33, p. 221, 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim DOI: 10.1002 / 14356007.a24_219).

[0005] There therefore remains a need for new compositions exhibiting antimicrobial properties.

[0006] In particular, there is a need for new compositions particularly suitable for use in cosmetic compositions comprising one or more surfactants, in particular micellar solutions.

[0007] There is a particular need for compositions that produce micellar solutions offering both optimal microbiological protection and good ocular tolerance, while also ensuring effective makeup removal. Furthermore, these micellar solutions must be stable over time and / or not develop any odor or unpleasant odor over time.

[0008] The inventors have surprisingly discovered that combining at least one compound of formula (I) as defined below with at least one compound of formula (II) and / or (II') as defined below yields a composition that meets these requirements. The compositions according to the invention are particularly well-suited for use in micellar solutions. The compositions according to the invention make it possible to provide micellar solutions that offer both optimal microbiological protection and effective makeup removal. Furthermore, 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 exhibit any change in odor and / or visual appearance over time (such as cloudiness).

[0009] More specifically, the present invention relates to a composition, preferably antimicrobial, comprising:

[0010] (i) at least one compound of formula (I) and / or its salts, and / or its solvates, R2 R3 (0

[0011] in which:

[0012] - RI represents a (Ci-C4)alkyl group such as methyl or ethyl, preferably ethyl;

[0013] - R2 represents a hydrogen atom or an (Ci-C4)alkyl group such as methyl or ethyl, preferably R2 represents a hydrogen atom;

[0014] - R3 represents a linear (Ci-C6)alkyl group, a branched (C3-C6)alkyl group or a group (C2-C6)linear alkenyl or (C3-C6)branched alkenyl;

[0015] - X represents an oxo group =0 or hydroxyl OH, preferably X represents =0; And

[0016] (ii) at least one compound of formula (II) and / or (II'), and / or their stereoisomers, and / or their salts, and / or their solvates such as hydrates:

[0017] [Chem.2] (H)

[0019] wherein R' represents an aliphatic chain, linear or branched, cyclic or acyclic, saturated or unsaturated, comprising from 1 to 16 carbon atoms, and M+, when present, represents a cationic counterion, in particular an alkali metal such as sodium and potassium, an alkaline earth metal such as calcium, or the ammonium ion.

[0020] Said composition is preferably antimicrobial, also called "preferably antimicrobial composition".

[0021] The present invention also relates to a cosmetic composition, preferably for skin and / or hair, preferably a makeup-removing composition, comprising, in a physiologically acceptable environment, a composition according to the invention.

[0022] Another object of the invention is the use of i) at least one compound (I) associated with ii) at least one compound (II) and / or (II') as an antimicrobial agent, in particular on the germs Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Ente-rococcus faecalis, Candida albicans and Aspergillus niger, in particular on the strain Aspergilus niger.

[0023] The present invention also relates to a method for preserving a cosmetic composition, in particular comprising a physiologically acceptable medium, including the mixture of said cosmetic composition with a composition according to the invention.

[0024] The present invention therefore also relates to a method for preserving a cosmetic formulation, in particular comprising a physiologically acceptable medium, comprising mixing said cosmetic formulation with a composition according to the invention.

[0025] The present invention also relates to a non-therapeutic cosmetic treatment method, in particular for the care and / or makeup and / or cleaning of keratinous materials, comprising the application to said keratinous materials of a cosmetic composition according to the invention.

[0026] i) Compound of formula (I)

[0027] The preferred antimicrobial composition and the cosmetic composition according to the invention comprise one or more compounds of formula (I) as defined above and / or any of its salts, and / or any of its solvates.

[0028] In particular, the compound(s) of formula (I) are such that, taken together or separately, (preferably taken together):

[0029] - RI represents a methyl or ethyl radical;

[0030] - R2 represents a hydrogen atom or a methyl or ethyl radical;

[0031] - R3 represents a linear (Ci-C6) alkyl; and

[0032] - X represents =0 or OH.

[0033] More particularly, the compounds of formula (I) are such that, taken together or separately (preferably taken together):

[0034] - RI represents a methyl or ethyl radical, preferably ethyl;

[0035] - R2 represents a hydrogen atom or a methyl or ethyl radical, preferably a hydrogen atom;

[0036] - R3 represents a linear (Ci-C6)alkyl, preferably a methyl;

[0037] - X represents =0.

[0038] According to a particular embodiment of the invention, the compound(s) of formula (I) are 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one and / or any of its salts, and / or any of its solvates.

[0039] 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one (also known as ethylzingerone (EZ)) is the compound with the formula (la):

[0040] [Chem.4] O (fe)

[0041] 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one can be in solvated form, in particular hydrated.

[0042] 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one can be in salified form with an organic or mineral base and have the following formula (la'):

[0043] [Chem.5] O (there')

[0044] wherein M+ represents a cationic counter-ion, in particular an alkali metal such as sodium and potassium, an alkaline earth metal such as calcium, or the ammonium ion.

[0045] ii) Compound of formula (II) and / or (II')

[0046] The preferably antimicrobial composition and the cosmetic composition according to the invention comprise one or more compounds of formula (II) and / or (II') as defined above, and / or any of its stereoisomers, and / or any of its salts, and / or any of its solvates such as its hydrates,

[0047] Preferably, 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.

[0048] According to one embodiment of the invention, the aliphatic chain is acyclic.

[0049] According to one embodiment of the invention, the aliphatic chain is linear.

[0050] According to one embodiment of the invention, the aliphatic chain is saturated.

[0051] Preferably, the salts of the compounds of formula (II) are organic base salts or mineral.

[0052] Preferably, the salts of the compounds of formula (II) are salts of alkali metals such as sodium or potassium, salts of alkaline earth metals such as calcium, or salts of ammonium ions, preferably salts of sodium ions.

[0053] Preferably, the salts of the compounds of formula (II) are chosen from the salts of the following formula and their stereoisomers:

[0054] - salts of formula (Il-a)

[0055] [Chem.6]

[0056] - salts of formula (Il-b),

[0057] [Chem.7] , And

[0058] - salts of formula (II-c)

[0059] [Chem. 8]

[0060] in which M+ represents a cationic counter-ion, in particular an alkali metal such as sodium and potassium, an alkaline earth metal such as calcium, or the ammonium ion.

[0061] According to another particular embodiment of the invention, the preferably antimicrobial composition and the cosmetic composition according to the invention comprise one or more compounds of formula (II') as defined above, as well as their stereoisomers, their salts and solvates such as hydrates.

[0062] Preferably, the salts of the compounds of formula (II') are sodium ion salts.

[0063] Preferably, the compound(s) of formula (II) are present in the preferably antimicrobial composition according to the invention in the form of a salt, in particular a sodium, monosodium, or disodium salt. The preferably antimicrobial composition and the cosmetic composition according to the invention therefore preferably comprise a compound of formula (II).

[0064] Preferably, the compound of formula (II) is spiculisporic acid, also known as 4,5-dicarboxy-4-pentadecanolide, as well as its stereoisomers, salts, and solvates such as hydrates. Spiculisporic acid has the following formula (II-d):

[0065] [Chem.9] (Hd).

[0066] Preferably, the preferably antimicrobial composition and / or the cosmetic composition according to the invention, have a weight ratio between the content by weight of compound(s) of formula (II) and / or (II') as defined above, in particular of formula (II), and the content by weight of compound(s) of formula (I) as defined above, in particular 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one, of 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. Cosmetic composition

[0067] The cosmetic composition according to the invention comprises, in a physiologically acceptable medium, the preferably antimicrobial composition according to the invention.

[0068] Preferably, in the cosmetic composition according to the invention, the compound(s) of formula (I) as defined above, in particular 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one, are present in a content of between 0.01% and 2% by weight relative 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%.

[0069] Preferably, in the cosmetic composition according to the invention, the compound(s) of formula (II) and / or (II'), in particular of formula (II) such as of formula (II-d), are present in a content of between 0.01% and 2% by weight relative 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%.

[0070] The cosmetic composition according to the invention comprises a physiologically acceptable medium. By physiologically acceptable medium, we mean a medium compatible with the skin, mucous membranes and / or hair.

[0071] Aqueous phase

[0072] Preferably, the cosmetic composition according to the invention comprises an aqueous phase.

[0073] The aqueous phase contains water.

[0074] The water used may be sterile demineralized water and / or floral water such as rose water, cornflower water, chamomile water or linden water, and / or natural thermal or mineral water, such as, for example: Vittel water, Vichy basin waters, Uriage water, La Roche-Posay water, La Bourboule water, Enghien-les-Bains water, Saint-Gervais-les-Bains water, Néris-les-Bains water, Allevar-les-Bains water, Digne water, Maizières water, Neyrac-les-Bains water, Lons-le-Saunier water, Eaux-Bonnes water, Rochefort water, Saint-Christau water, Fumades water and water From Tercis-les-bains, Avène water.

[0075] The aqueous phase may contain at least one organic solvent that is soluble or miscible in water at 25°C.

[0076] Water-soluble or miscible solvents suitable for the invention include (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, such as 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.

[0077] The quantity of solvents soluble or miscible in water is preferably from 0.01% to 15% by weight, preferably from 1% to 10% by weight, better from 2% to 8% by weight, better from 3% to 5% by weight relative to the total weight of the cosmetic composition.

[0078] According to a particular embodiment of the invention, the aqueous phase represents from 15% to 97% by weight, preferably from 30% to 90% by weight, even better from 45% to 90% by weight relative to the total weight of the cosmetic composition.

[0079] According to another particular embodiment of the invention, the aqueous phase represents 100% by weight of the cosmetic composition, for example when the cosmetic composition is a micellar solution or a micellar jelly.

[0080] According to a particular embodiment of the invention, the cosmetic composition of the invention is micellar, i.e., is in the form of a micellar structure, preferably of spherical micellar structure. The micelles can be direct or reverse, preferably direct.

[0081] iii) Surfactant

[0082] According to one embodiment of the invention, the cosmetic composition further comprises iii) one or more surfactants different from the compounds of formula (II) and (II').

[0083] The surfactant(s) iii) of the invention may be chosen from non-ionic, anionic, zwitterionic or amphoteric surfactants.

[0084] Preferably, the cosmetic composition comprises an amount of cationic surfactant less than or equal to 1.5% by weight relative to the total weight of the cosmetic composition, preferably in an amount less than or equal to 1%, more particularly less than or equal to 0.5% by weight relative to the total weight of the cosmetic composition, even more preferably the cosmetic composition comprises an amount less than 0.5%, or even better, the cosmetic composition of the invention does not comprise any cationic surfactant. According to a preferred embodiment of the invention, the surfactant(s) are nonionic or anionic, preferably nonionic.

[0085] Among the non-ionic surfactant(s), the following may be cited, alone or in mixtures: 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 comprising, for example, 8 to 30 carbon atoms, in particular comprising 10 to 22 carbon atoms, the number of ethylene oxide or propylene oxide groups being able to range in particular from 2 to 200, in particular from 10 to 100 and the number of glycerol groups being able to range in particular from 2 to 200, in particular from 10 to 100.Other examples include ethylene oxide (EO) and propylene oxide (PO) copolymers, ethylene oxide and propylene oxide condensates on fatty alcohols; polyethoxylated fatty amides preferably having 2 to 30 moles EO, polyglycerol fatty amides having on average 1 to 5 glycerol groups and in particular 1.5 to 4; oxyethylenated sorbitan fatty acid esters having 2 to 200 moles EO, in particular 10 to 100 EO; sucrose fatty acid esters, polyethylene glycol fatty acid esters, alkyl polyglycosides, N-alkyl glucamine derivatives, amine oxides such as alkyl (CiO-Ci4)amine oxides or N-acylaminopropylmorpholine oxides.

[0086] Preferably, the non-ionic surfactant(s) are chosen from: (poly)ethoxylated fatty alcohols; glycerolized fatty alcohols; alkyl polyglycosides, preferably mono- and diesters of sorbitan fatty acids oxyethylenated having 2 to 200 moles OE, in particular 10 to 100 OE and alkyl polyglycosides such as caprylyl / capryl glucoside.

[0087] Preferably, the surfactant(s) are chosen from mono- and diesters of oxyethylenated sorbitan fatty acids having from 2 to 200 moles OE, in particular from 10 to 100 OE such as propylene glycol stearate having from 10 to 30 OE such as 20 OE; glyceryl mono distearate / polyethylene glycol stearate (100 OE).

[0088] By fatty chain, we mean a hydrocarbon chain comprising 6 to 30 carbon atoms, preferably 8 to 24 carbon atoms, linear or branched, saturated or unsaturated, such as stearyl.

[0089] With regard to alkyl polyglycosides, these compounds can be represented by the following general formula: RiO-(R2O)t (G)v (III) in which:

[0090] - R represents a linear or branched alkyl and / or alkenyl radical comprising approximately of 8 to 24 carbon atoms, an alkylphenyl radical whose linear or branched alkyl radical comprises of 8 to 24 carbon atoms;

[0091] - R2 represents an alkylene radical comprising approximately 2 to 4 carbon atoms;

[0092] - G represents a sugar motif comprising 5 to 6 carbon atoms;

[0093] -1 denotes an integer between 0 and 10 inclusive, preferably between 0 and 4, preferably between 0 and 4; and

[0094] - v denotes an integer between 1 and 15.

[0095] Preferred alkylpolyglycosides according to the present invention are compounds of formula (HD) in which Ri more particularly designates a saturated or unsaturated, linear or branched alkyl radical comprising 8 to 18 carbon atoms, t designates a value from 0 to 3 and more particularly equal to 0, G may designate glucose, fructose or galactose, preferably glucose. The degree of polymerization, i.e. the value of v in formula (III), may range from 1 to 15, preferably from 1 to 4. The average degree of polymerization is more particularly between 1 and 2 and even more preferably from 1.1 to 1.5.

[0096] The glycosidic bonds between the sugar motifs are of the 1-6 or 1-4 type and preferably 1-4.

[0097] Compounds of formula (III) are notably represented by the products sold by COGNIS under the names PLANTAREN® (600 CS / U, 1200 and 2000) or PLANT AC ARE® (818, 1200 and 2000). Products sold by SEPPIC under the names TRITON CG 110 (or ORAMIX CG 110) and TRITON CG 312 (or ORAMIX® NS 10), products sold by BASF under the name LUTENSOL GD 70, or those sold by CHEM Y under the name AGIO LK may also be used.

[0098] One can also use, for example, Alkyl in C8 / Ci6 polyglucoside 1,4 in aqueous solution at 53% marketed by COGNIS under the reference PLANTACARE® 818 UP.

[0099] With regard to mono- or polyglycerol surfactants, they preferably comprise on average from 1 to 40 glycerol groups, more particularly from 10 to 30 glycerol groups such as 20.

[0100] According to a particular embodiment of the invention, the surfactants are mono-glycerolated or polyglycerolated and are preferably chosen from compounds with the following formulas: RO[CH2CH(CH2OH)O]mH,

[0101] RO[CH2CH(OH)CH2O]mH or

[0102] RO[CH(CH2OH)CH2O]mH ;

[0103] in which:

[0104] - R represents a saturated or unsaturated, linear or branched hydrocarbon radical, comprising 8 to 40 carbon atoms and preferably 10 to 30 carbon atoms;

[0105] - m is a number between 1 and 30, preferably between 1 and 10, more particularly R is a group of 1.5 to 6. R may optionally include heteroatoms such as oxygen and nitrogen. In particular, R may optionally include one or more hydroxyl and / or ether and / or amide groups. R preferably denotes alkyl and / or alkenyl radicals of the form CiO-C2O, possibly mono- or polyhydroxylated.

[0106] Fatty (poly)ethoxylated alcohols are more particularly chosen from among alcohols having 8 to 30 carbon atoms, and preferably 12 to 22 carbon atoms.

[0107] Fatty (poly)ethoxylated alcohols more particularly have one or more hydrocarbon groups, linear or branched, saturated or unsaturated, comprising 8 to 30 carbon atoms, optionally substituted, in particular by one or more hydroxyl groups (in particular 1 to 4). If they are unsaturated, these compounds may comprise one to three carbon-carbon double bonds, conjugated or not.

[0108] The (poly)ethoxylated fatty alcohol(s) preferably have the following formula: Ra-[O-CH2-CH2]n-OH

[0109] with

[0110] - Ra representing a linear or branched Ci-C40 alkyl group, or linear alkenyl or branched at C2-C30 (preferably alkyl at C8-C30); and

[0111] - n represents an integer between 1 and 200 inclusive, preferably between 2 and 100, more particularly inclusively between 10 and 50, even more particularly inclusively between 15 and 30 such as 100 or 20.

[0112] Fatty (poly)ethoxylated alcohols are more particularly fatty alcohols comprising 8 to 22 carbon atoms and oxyethylenated with 1 to 30 moles of ethylene oxide (1 to 100 EO). Among them, the following may be mentioned more particularly: lauryl alcohol 20 EO, lauryl alcohol 30 EO, decyl alcohol 3 EO, decyl alcohol 5 EO and oleyl alcohol 20 EO.

[0113] Mixtures of these (poly)oxyethylenated fatty alcohols can also be used.

[0114] Non-ionic surfactants are preferably alkyl C6-C24 polyglucosides and fatty (poly)ethoxylated alcohols and more particularly alkyl C8-Ci6 polyglucoside.

[0115] The quantity of non-ionic surfactants preferably 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 relative to the total weight of the cosmetic composition of the invention.

[0116] According to another particular embodiment of the invention, the cosmetic composition comprises one or more anionic surfactants.

[0117] The term "anionic surfactant" means a surfactant comprising only anionic groups as ionic or ionizable groups. These anionic groups are preferably chosen from among the groups -C(O)OH, -C(O)O, -SO3H, -S(O)2O, -OS(O)2OH, -OS(O)2O, -P(O)2OH, -P(O)2O, -P(O)O2, -P(OH)2, =P(O)OH, -P(OH)O, =P(O)O, =POH, =PO, the anionic parts comprising a cationic counter ion such as an alkali metal, an alkaline earth metal, or an ammonium, more preferably the groups are carboxy-C(O)OH, or carboxylate -C(O)O.

[0118] Examples of anionic surfactants include alkylcarboxylic acids, alkyl sulfates, alkyl ether sulfates, alkylamidoethersulfates, alkylarylpolyethersulfates, monoglyceride sulfates, alkylsulfonates, alkylamide sulfonates, alkylarylsulfonates, alpha-olefin sulfonates, paraffin sulfonates, alkylsulfosuccinates, alkylethersulfosuccinates, alkylamide sulfosuccinates, alkylsulfoacetates, acylsarcosinates, acylglutamates, alkylglycinates, alkylsulfosuccinamates, acylisethionates and N-acyltaurates, salts of alkyl monoesters and polyglycoside polycarboxylic acids, alkyl diester salts and polyglycoside-polycarboxylic acids, acyllactylates, D-galactoside-uronic acid salts, alkyl ether-carboxylic acid salts, alkylaryl ether-carboxylic acid salts, alkyl amidoether-carboxylic acid salts,and the corresponding non-salted forms of all these compounds, the alkyl and acyl groups of all these compounds having from 8 to 30 carbon atoms, preferably from 10 to 22 carbon atoms, and the aryl group designating a phenyl group.

[0119] These compounds can be oxyethylated and then preferably comprise from 1 to 50 ethylene oxide motifs.

[0120] The salts of C6-C24 alkyl monoesters and polyglycoside-polycarbyl acids can be selected from C6-C24 alkyl polyglycoside-citrates, C6-C24 alkyl polyglycoside-tartrates and C6-C24 alkyl polyglycoside-sulfosuccinates.

[0121] When the anionic surfactant(s) are in salt form, it / they may be chosen from among alkali metal salts such as sodium or potassium salt and preferably sodium salt, ammonium salts, amine salts and in particular amino alcohols or alkaline earth metal salts such as magnesium salts.

[0122] Examples of amino alcohol salts include mono-, di- and triethanolamine salts, mono-, di- or triisopropanolamine salts, 2-amino-2-methyl-1-propanol salts, 2-amino-2-methyl-1,3-propanediol and tris(hydroxy-methyl)aminomethane salts.

[0123] Salts of alkali or alkaline earth metals are preferably used, and in particular salts of sodium or magnesium.

[0124] Among the anionic surfactants mentioned, preferred are alkyl(C6-C24)carboxylic acids, in particular alkyl(C10-C2o)carboxylic acids, preferably of natural origin, in particular vegetable such as stearic acid, which may be in the form of salts of alkali metals, ammonium, amino alcohols, and alkaline earth metals, or a mixture of these compounds; acylglutamates such as disodium cocoyl glutamate; acylglycinates such as sodium N-cocoyl glycinate.

[0125] Examples of amphoteric surfactants include alkylbetaines or alkylamidopropylbetaines, such as coco-betaine and cocamidopropylbetaine.

[0126] The quantity of anionic surfactants preferably 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 relative to the total weight of the cosmetic composition of the invention.

[0127] The quantity of surfactants 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% relative to the total weight of the cosmetic composition of the invention.

[0128] iv) Hydrophilic gelling agent

[0129] The cosmetic composition according to the invention may optionally include a hydrophilic gelling agent, particulate or non-particulate, synthetic or of natural origin.

[0130] Examples of hydrophilic gelling agents include carboxy-vinyl polymers such as Carbopols (Carbomers) and Pemulen (acrylate / C10-C30-alkylacrylate copolymer); polyacrylamides such as crosslinked copolymers sold under the names Sepigel 305 (CTFA name: polyacrylamide / C13-14 isoparaffin / Laureth 7) or Simulgel 600 (CTFA name: acrylamide / sodium acryloyl-dimethyltaurate copolymer / isohexadecane / polysorbate 80) by the company Seppic; 2-acrylamido-2-methylpropane sulfonic acid polymers and copolymers, possibly crosslinked and / or neutralized, such as poly(2-acrylamido-2-methylpropane sulfonic acid) marketed by Hoechst under the trade name "Hostacerin AMPS" (CTFA name: ammonium polyacryloyl- dimethyl taurate or SIMULGEL 800 marketed by SEPPIC (CTFA name: sodium polyacryolyldimethyl taurate / polysorbate 80 / sorbitan oleate); copolymers of 2-acrylamido 2-methylpropane sulfonic acid and hydroxyethyl acrylate such as SIMULGEL NS and SEPINOV EMT 10 marketed by SEPPIC; cellulosic derivatives such as hydroxyethylcellulose; polysaccharides and in particular gums such as Xanthan gum; or sodium alginate; and mixtures thereof.

[0131] According to one embodiment, the hydrophilic gelling agent comprises at least xanthan gum.

[0132] According to one embodiment, the hydrophilic gelling agent is a mixture of one or more of the compounds listed above.

[0133] According to one embodiment, the hydrophilic gelling agent is selected from xanthan gum, acrylamide and sodium acryloyldimethyltaurate copolymers and any of their mixtures.

[0134] The quantity of gelling agent preferably ranges from 0.01% to 30% by weight, preferably from 1% to 15% by weight, more preferably from 2% to 7% by weight, more preferably from 3% to 5% by weight, relative to the total weight of the cosmetic composition of the invention. For example, the quantity of gelling agent ranges from 0.1% to 0.5% by weight relative to the total weight of the cosmetic composition of the invention.

[0135] Advantageously, the cosmetic composition according to the invention is a micellar solution, a micellar jelly or a micellar biphasic composition.

[0136] According to the invention, a micellar solution is a single-phase aqueous solution comprising an aqueous phase and at least one surfactant.

[0137] According to the invention, a micellar jelly is a gelled monophasic aqueous solution, i.e. comprising an aqueous phase, at least one surfactant, and iv) at least one gelling agent as defined above.

[0138] According to another embodiment, the cosmetic composition according to the invention is a micellar biphasic composition.

[0139] According to the invention, a micellar biphasic composition comprises an aqueous phase, at least one surfactant, and v) one or more fatty substances.

[0140] By "fats and oils," we mean an organic compound insoluble in water at ordinary room temperature (25°C) and atmospheric pressure (760 mm Hg) (solubility less than 5% and preferably less than 1%, and even more preferably less than 0.1%). They have in their structure at least one hydrocarbon chain comprising at least 6 carbon atoms or a chain of at least two siloxane groups. Furthermore, fats and oils are generally soluble in organic solvents under the same conditions of temperature and pressure, such as, for example, chloroform, ethanol, benzene, petrolatum, or decamethyl cy- clopentasiloxane.

[0141] The fat(s) of the invention are of natural or synthetic origin, preferably natural, more preferably of vegetable origin. They differ from fatty acids because saline fatty acids constitute soaps that are generally soluble in aqueous media.

[0142] Preferably, the cosmetic composition contains one or more fatty substances (v) which are hydrocarbon-based liquid fatty substances at 25°C and atmospheric pressure. The hydrocarbon-based liquid fatty substance(s) are chosen in particular from hydrocarbons and are of the C6-Ci6 type or have more than 16 carbon atoms up to 60 carbon atoms, preferably between C6 and Ci6, and in particular alkanes, oils of animal origin, oils of vegetable origin, glycerides or fluorinated oils of synthetic origin, fatty alcohols, esters of fatty acids and / or fatty alcohols, and silicones. In particular, the liquid fatty substance(s) are chosen from non-siliconized oils.

[0143] In particular, the cosmetic composition comprises at least one liquid hydrocarbon oil selected from:

[0144] - vegetable oils formed by esters of fatty acids and polyols, in particular triglycerides, such as sunflower, sesame or rapeseed oil, macadamia, soybean, sweet almond, calophyllum, palm, grapeseed, corn, arara, cottonseed, apricot, avocado, jojoba, olive, coconut or cereal germ oil;

[0145] - linear, branched or cyclic esters, having more than 6 carbon atoms, including 6 to 30 carbon atoms; and in particular isononyl isononanoate;

[0146] and more particularly esters of formula Rd-C(O)-O-Re in which Rd represents the remainder of a higher fatty acid comprising 7 to 19 carbon atoms and Re represents a hydrocarbon chain comprising 3 to 20 carbon atoms, such as palmitates, adipates, myristates and benzoates, in particular diisopropyl adipate and isopropyl myristate; more preferably esters of formula Rd-C(O)-O-Re in which Rd represents the remainder of a higher fatty acid comprising 8 to 10 carbon atoms and Re represents a hydrocarbon chain comprising 12 to 18 carbon atoms;

[0147] - hydrocarbons, and in particular linear, branched and / or cyclic alkanes, volatile or non-volatile, such as C5-C60 isoparaffins, possibly volatile such as undecane, dodecane, isododecane, tridecane, Parleam (hydrogenated polyisobutene), isohexadecane, cyclohexane, or 'ISOPARs', and mixtures thereof; or alkanes obtained from the complete hydrogenation / reduction of fatty acid mixtures from Cocos Nucifera (coconut) oil such as dodecane, mixtures of C9-C12 alkanes, the chains of which comprise 9 to 12 carbon atoms, preferably linear or branched alkanes, in particular C9-C12 alkanes comprising dodecane, or paraffin oils, petroleum jelly, or hydrogenated polyisobutylene

[0148] - ethers having 6 to 30 carbon atoms;

[0149] - ketones having 6 to 30 carbon atoms;

[0150] - aliphatic fatty monoalcohols having 6 to 30 carbon atoms, the hydro chain carbonaceous not containing a substitution group, such as oleic alcohol, decanol, dodecanol, octadecanol, octyldodecanol and linoleic alcohol;

[0151] - polyols having 6 to 30 carbon atoms, such as hexylene glycol; and

[0152] - their mixtures, such as mixtures of linear or C8 branched fatty acid esters -Cio and fatty alcohols in Ci2-Ci8 and alkanes from the complete hydrogenation / reduction of fatty acid mixtures from Cocos Nucifera (Coconut) oil, in particular dodecane such as cococaprylate / caprate and dodecane mixtures, examples include those with INCI name coconut alkanes (and) Coco-caprylate / caprate marketed under the name VEGELIGHT 1212LC® by Grant Industries; or mixtures of C9-C12 alkanes, whose chains comprise 9 to 12 carbon atoms, preferably linear or branched alkanes, in C9-C12 in particular including dodecane, examples include the oil mixture with INCI name C9-12 ALKANE, VEGELIGHT SILK® marketed by BioSynthls.

[0153] Advantageously, the cosmetic composition comprises one or more fatty substances, in particular liquids at 25 °C and atmospheric pressure, preferably one or more oils, in a content ranging from 0.01 to 90% by weight, relative 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.

[0154] Preferably, the cosmetic composition according to the invention is substantially free of cationic antimicrobial agent.

[0155] By "substantially free" is meant that the cosmetic composition comprises less than 0.01% by weight relative to the total weight of the cosmetic composition, preferably less than 0.005% by weight of a cationic antimicrobial agent. Preferably, the cosmetic composition according to the invention is totally free of cationic antimicrobial agents.

[0156] By cationic antimicrobial agent, we mean for example quaternary ammonium salts such as, for example, benzalkonium chloride, or biguanide.

[0157] The present invention also relates to a non-therapeutic cosmetic treatment method, in particular for the care and / or makeup and / or cleaning of keratinous materials, preferably for the removal of makeup from keratinous materials, comprising the application to said keratinous materials of a cosmetic composition according to the invention.

[0158] The expressions "between ... and ...", "ranging from ... to ..." and "varies from ... to ..." "should be understood inclusive of the terminals, unless otherwise specified.

[0159] Unless otherwise stated:

[0160] By "alkyl" we mean a hydrocarbon chain, linear or branched.

[0161] By "alkenyl" is meant a hydrocarbon chain, linear or branched, comprising one or more unsaturations, conjugated or not.

[0162] Concrete, but by no means limiting, examples illustrating the invention will now be given. Examples

[0163] Example 1: Determination of antimicrobial activity synergy

[0164] Experimental conditions:

[0165] The association of at least one compound of formula (I) such that the 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one (substance A) and at least one compound of formula (II) and / or (II') such as spiculisporic acid (substance B) was tested on a strain of Aspergillus niger, from the collection of the American Type Collection (ATCC) and is maintained in the laboratory according to the requirements of standard NF EN 12353.

[0166] The culture medium is a Sabouraud broth supplemented with polyoxyethylenated sorbitan monopalmitate (20 OE) (Tween 40 from Croda) and Phytagel© BioReagent, at double concentration (i.e. a mixture of 5 g of Phytagel + 0.6 g of tween 40 + 60 g of Sabouraud broth).

[0167] The incubation temperature of the microplate is 30 °C + / - 1 °C under aerobic conditions.

[0168] The incubation time of the microplate is 18 h to 48 h under aerobic conditions. Preparation of daughter solutions of A and B

[0169] Stock solutions of A and B are prepared in 1% agar. Successive dilutions in 1% agar are carried out.

[0170] The range of product concentrations tested in the final brackets the MIC value of each product according to the principle: MC 1 / 8, MC 1 / 4, MIC / 2, MIC and 2 MIC. Tests of compounds A and B alone

[0171] 50 pL of each of the daughter solutions obtained containing compound A or B is added to the wells of the microplate. Also added are 100 pL of Sabouraud liquid nutrient broth inoculated at double concentration with the Aspergillus niger strain and 50 pL of an aqueous solution of 1% agar. Tests of compounds A and B in mixture

[0172] 50 pL of each of the daughter solutions obtained containing compound A and 50 pL of Each of the daughter solutions obtained, containing compound B, is added to the wells of the microplate. Also added are 100 µL of Sabouraud liquid nutrient broth inoculated at double concentration with the Aspergillus niger strain. Absorbance control for compounds A and B alone

[0173] An absorbance control of compounds A and B alone was prepared in parallel. This control consisted of 100 pL of sterile Sabouraud liquid nutrient broth at double concentration, 50 pL of each of the daughter solutions obtained containing compound A or B, and 50 pL of a 1% aqueous agar solution. Microbial growth control

[0174] A positive microbial growth control was also prepared. The positive microbial growth control consisted of mixing 100 pL of an aqueous 1% agar solution with 100 pL of Sabouraud liquid nutrient broth inoculated at double concentration with the Aspergillus niger strain in the absence of compounds A and B.

[0175] In all cases (absorbance control, growth control and assays), the final volume present in each well of the microplate is 200 pL. Results

[0176] The antimicrobial efficacy improvement effect of the combination of A and B, in particular the synergy of A and B, was determined by calculating the synergy index (or FIC index), according to the following formula:

[0177] FIC Index = (CMI of A with B / CMI of A) + (CMI of B with A / CMI of B)

[0178] with:

[0179] - MIC of A with B: minimum concentration of product A in the A + B combination allowing for an inhibitory effect;

[0180] - MIC of B with A: minimum concentration of product B in the A + B combination enabling the inhibitory effect to be achieved;

[0181] - MIC of A: minimum inhibitory concentration of product A alone;

[0182] - MIC of B: minimum inhibitory concentration of product B alone.

[0183] This formula was first described in the article by FC Kull, PC Eisman, HD Sylwestrowka, and RL Mayer, Applied Microbiology 9:538-541, 1961.

[0184] For each compound tested alone, the MIC is considered to be the first concentration allowing a percentage of microbial growth to be less than or equal to 20%.

[0185] Regarding the tested combinations, MIC of A with B and MIC of B with A are the respective concentrations of A and B in the combinations allowing the obtaining of a percentage of microbial growth less than or equal to 20%.

[0186] The percentage growth is calculated as follows:

[0187] Percentage growth = (DO product at concentration C - DO control absorbance at concentration C) / DO control growth

[0188] When the value of the FIC index is less than or equal to 0.75, the combination of the tested compounds is considered to have a synergistic effect.

[0189] The results obtained are as follows:

[0190] CMI of A: 0.2%

[0191] CMI of B: > 2%

[0192] CMI of A with B: 0.1%

[0193] CMI of B with A: 0.125%

[0194] FIC Index: < 0.625

[0195] These results demonstrate a significant improvement (or even a synergistic effect since the FIC is less than 0.75) in terms of antimicrobial activity of the association 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 (IF) such as spiculisporic acid.

[0196] Furthermore, no change in the odor of the formula or in the appearance of the composition of the invention comprising A and B was noted, even after 2 months and at room temperature, at 45°C or at 4°C.

[0197] Example 2: Makeup-removing cosmetic composition according to the invention

[0198] A makeup-removing composition (micellar solution) was prepared from the ingredients listed in the following table

[0199] [Tables] Chemical Name Concentration (% by weight) L-Arginine 0.7 Spiculisporic (II) acid 0.8 Sodium N-cocoyl glycinate (in 30% aqueous solution) 0.5 Disodium cocoyl glutamate (in 25% aqueous solution) 4 Propane-1,3-diol 3.5 4-(3-ethoxy-4-hydroxyphenyl)butan-2-one (I) (in water and propanediol) (90% MA) 0.78 Microbiologically clean deionized water q.s. 100

[0200] Microbiological tests were carried out on this composition and showed that it provides satisfactory antimicrobial protection at 7 days, 14 days, and 28 days against the germs Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Enterococcus faecalis, Candida albicans, and Aspergillus niger. Furthermore, the composition easily and effectively removes makeup from the face and lips. eyelids, eyelashes and eyebrows.

[0201] Example 3: Micellar cosmetic compositions according to the invention

[0202] Three other makeup-removing compositions were prepared from the ingredients listed in the following table

[0203] [Tables2] Chemical Name: Semi-cellular Solution, Semi-cellular Jelly, Biphasic Semi-cellular Concentration (% by weight) L-Arginine 0.7 0.9 0.3 Spiculisporic Acid (II) 0.8 1 0.5 Glycerin 1 1 1 Caprylyl / capryl glucoside 1.7 - - Coco betaine 0.5 - - Propane-1,3-diol 3 3.5 3 Sodium alginate - 0.25 - 4-(3-ethoxy-4-hydroxyphenyl)butane-n-2-one (I) (in water and propanediol) (90% MA) 0.7 0.5 0.5 Isopropyl myristate - - 14 Dicaprylyl ether - - 5 Microbiologically clean deionized water Qsp 100 Qsp 100 Qsp 100

[0204] As with the previous example, it appeared that the compositions proved to be active on different microbial strains which effectively remove makeup from the face, lips, eyelids, eyelashes and eyebrows.

Claims

1. Demands Composition, preferably antimicrobial, comprising: (i) at least one compound of formula (I) and / or its salts, and / or its solvates, R2 R3 (I) in which: - RI represents an (Ci-C4)alkyl group, such as methyl or ethyl, preferably ethyl; - R2 represents a hydrogen atom or an (Ci-C4)alkyl group such as methyl or ethyl, preferably R2 represents a hydrogen atom; - R3 represents a linear (Ci-C6)alkyl group, a branched (C3-C6)alkyl group, or a linear (C2-C6)alkenyl group or a branched (C3-C6)alkenyl group; - X represents an oxo group (OH), preferably X represents 0; and (ii) at least one compound of formula (II) and / or (II'), and / or their stereoisomers, and / or their salts, and / or their solvates such as hydrates:

2. in which R' represents an aliphatic chain, linear or branched, cyclic or acyclic, saturated or unsaturated, comprising from 1 to 16 carbon atoms, and M+, when present, represents a cationic counterion, in particular an alkali metal such as sodium and potassium, an alkaline earth metal such as calcium, or the ammonium ion. Composition according to claim 1, wherein the weight ratio the ratio between the weight content of compound(s) of formula (II) and / or (II') and the weight content of compound(s) of formula (I) is 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.

3. Composition according to claim 1 or 2, wherein the compound of formula (II) and / or (II') is spiculisporic acid of formula (Il-d): HO-O-OH and / or any of its stereoisomers, and / or any of its salts, and / or any of its solvates.

4. Cosmetic composition, preferably for skin and / or hair, preferably makeup-removing composition, comprising a composition according to any one of claims 1 to 3, in a physiologically acceptable medium.

5. Cosmetic composition according to claim 4, characterized in that the compound(s) of formula (I) are present in a content of between 0.01% and 2% by weight relative 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%.

6. Cosmetic composition according to claim 4 or 5, characterized in that the compound(s) of formula (II) and / or (II') are present in a content of between 0.01% and 2% by weight relative 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%.

7. Cosmetic composition according to any one of claims 4 to 6, further comprising an aqueous phase.

8. Cosmetic composition according to any one of claims 4 to 7, further comprising iii) or several surfactants different from the compounds of formula (II) and (II').

9. Cosmetic composition according to any one of claims 4 to 8, which is a micellar solution, a micellar jelly or a micellar biphasic composition.

10. Cosmetic composition according to any one of claims 4 to 9, being substantially free of cationic antimicrobial agent.

11. Use i) of at least one compound of formula (I) R2 R3 (1) in which: - RI represents an (Ci-C4)alkyl group such as methyl or ethyl, preferably ethyl; - R2 represents a hydrogen atom or an (Ci-C4)alkyl group such as methyl or ethyl, preferably R2 represents a hydrogen atom; - R3 represents a linear (Ci-C6)alkyl group, a branched (C3-C6)alkyl group, or a linear (C2-C6)alkenyl group or a branched (C3-C6)alkenyl group; and - X represents an oxo =0 or hydroxyl OH group, preferably X represents =0; associated with ii) at least one compound (II) and / or (II') in which R' represents an aliphatic chain, linear or branched, cyclic or acyclic, saturated or unsaturated, comprising from 1 to 16 carbon atoms, and M+, when present, represents a cationic counterion, in particular an alkali metal such as sodium and potassium, an alkaline earth metal such as calcium, or the ammonium ion, as an antimicrobial agent, particularly against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Enterococcus faecalis, Candida albicans and Aspergillus niger, especially against the Aspergilus niger strain.

12. A method for preserving a cosmetic composition, characterized in that it comprises mixing said cosmetic composition with a composition according to any one of claims 1 to 3.

13. A non-therapeutic cosmetic treatment process for keratinous materials, in particular for the care and / or makeup and / or cleansing of keratinous materials, preferably for the removal of makeup from keratinous materials, comprising the application to said keratinous materials of a cosmetic composition according to any one of claims 4 to 10.