WO2021122876A1 - Procédé de traitement de fibres de kératine à l'aide d'une composition comprenant un sel de carnitine ou un sel à base de carnitine comprenant un anion organique aromatique - Google Patents

Procédé de traitement de fibres de kératine à l'aide d'une composition comprenant un sel de carnitine ou un sel à base de carnitine comprenant un anion organique aromatique Download PDF

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Publication number
WO2021122876A1
WO2021122876A1 PCT/EP2020/086615 EP2020086615W WO2021122876A1 WO 2021122876 A1 WO2021122876 A1 WO 2021122876A1 EP 2020086615 W EP2020086615 W EP 2020086615W WO 2021122876 A1 WO2021122876 A1 WO 2021122876A1
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WIPO (PCT)
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group
compounds
formula
chosen
hydrogen atom
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PCT/EP2020/086615
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English (en)
Inventor
Andrew Greaves
Manon Chaumontet
Bérangère Baril
Maria Dalko
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L'oreal
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Publication of WO2021122876A1 publication Critical patent/WO2021122876A1/fr

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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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/002—Preparations for repairing the hair, e.g. hair cure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • the present invention relates to a process for treating keratin fibers, comprising the application of a composition comprising at least one carnitine salt or carnitine-based salt comprising an aromatic organic anion, for caring for and/or repairing keratin fibers.
  • the hair can be damaged and embrittled by external atmospheric agents such as pollution and bad weather, and also by mechanical or chemical treatments, or certain routines, such as brushing, combing, dyeing, bleaching, permanent-waving, relaxing and repeated washing.
  • the hair may end up damaged and may in the long run become dry, coarse, brittle, dull, split and/or limp.
  • carnitine or a salt thereof such as carnitine tartrate or carnitine lactate
  • carnitine tartrate or carnitine lactate can be used in hair compositions (see notably DE 195 39 859, EP 1 800 654 and EP 2 111 852).
  • certain organic acids can be used in hair compositions (see notably EP 0 978 272).
  • these compounds are not always entirely satisfactory with regard notably to preventing the breakage of the hair, for example during combing.
  • a subject of the present invention is a process for treating keratin fibers, comprising i) a step of applying to the keratin fibers a composition (A) comprising at least one compound of formula (I): in which: R 1 , R 2 and R 3 , which may be identical or different, represent a (hydroxy)(Ci-C4)alkyl group; R 4 represents a hydrogen atom, a (CrC4)alkyl group or a group -C(0)R, in which R is a (CrC3)alkyl group; R 5 represents a hydrogen atom, a (CrC4)alkyl group, an alkali metal or an alkaline-earth metal; An represents an aromatic organic anion chosen from the compounds of formula (II), (III) or (IV) below: in which:
  • R 6 to R 10 represent, independently of each other: • a hydrogen atom
  • a group -O-X in which X represents a hydrogen atom or a protecting group for the phenol function such as an acyl group, in particular an acetyl group; it being understood that two adjacent groups R 6 to R 10 may also form, together with the carbon atoms that bear them, a saturated or unsaturated or aromatic 5- or 6-membered (hetero)cycle;
  • R a , R b , R c , R d , R e and R f denote, independently of each other:
  • a (Ci-C 6 )alkyl group optionally substituted with one or more identical or different groups chosen from: -OR, -NR’R”, -C(0)0R, -0-C(0)-R, (hetero)cycle, -C(0)-R, -NH-C(0)-R, -C(O) -NH-R, with R, R’ and R” as defined previously, it being understood that the group -NR’R” is other than an -NH2 group;
  • a (Ci-C 6 )alkoxy group optionally substituted with one or more identical or different groups chosen from: -OR, -NR’R”, -C(0)0R, -0-C(0)-R, aryl and -CF 3 and/or optionally interrupted with one or more groups or heteroatoms chosen from: O, NR’, CO, S, SO and SO2, with R, R’ and R” as defined previously, it being understood that the group -NR’R” is other than an -NH2 group;
  • R a and R b may form, together with the carbon atom which bears them, a saturated or unsaturated, 4- to 8-membered, in particular 4- to 6-membered, (hetero)cycle, and more particularly a 5- or 6-membered carbocycle;
  • R a or R b or R c or R d may form with R 6 or R 10 and the carbon atoms that bear them a 4- to 8- membered (hetero)cycle, more particularly a 5- to 6-membered carbocycle; represents a single bond or an ethylenic double bond, it being understood that when represents an ethylenic double bond, R b and R c are absent;
  • - p is an integer equal to 0 or 1 ;
  • - r is an integer equal to 0 or 1 ;
  • R 11 represents a hydrogen atom, a negative charge, an alkali metal or an alkaline-earth metal, preferably a negative charge;
  • x is a stoichiometric coefficient chosen so as to ensure the electrical neutrality of the compound of formula (I).
  • a subject of the present invention is a composition (A) as defined above, it being understood that the composition does not comprise the compounds of formulae 1 to 4 below:
  • a subject of the present invention is the compounds of formulae 5 to 29 below and mixtures thereof:
  • a subject of the present invention is the cosmetic use of at least one compound of formula (I), as defined above, for caring for and/or repairing keratin fibers.
  • a subject of the present invention is the cosmetic use of at least one composition (A), as defined above, for caring for and/or repairing keratin fibers.
  • keratin fibers means fibers of human or animal origin, such as head hair, bodily hair, the eyelashes, the eyebrows, wool, angora, cashmere or fur. According to the present invention, the keratin fibers are preferably human keratin fibers, more preferentially the hair.
  • alkyl group means a linear or branched, saturated hydrocarbon-based radical.
  • (C x -C y )alkyl group means an alkyl group comprising from x to y carbon atoms, preferably methyl, ethyl, n-propyl, isopropyl or butyl, more preferentially methyl or n-propyl, even more preferentially methyl.
  • (C ⁇ C y )hydroxyalkyl group means a (C ⁇ C y )alkyl group, at least one of the hydrogen atoms of which is replaced with a hydroxyl (-OH) group.
  • alkoxy group means an alkyl group bonded to an oxygen atom.
  • (C x -C y )alkoxy group means an alkoxy group comprising from x to y carbon atoms.
  • (hetero)cycle means a heterocycle or a carbocycle.
  • heterocycle means a 4- to 8-membered, preferably 5- or 6-membered, saturated or unsaturated or aromatic cyclic group, the ring members of which consist of carbon atoms and of at least one heteroatom chosen from: O, S and N, preferably O and N.
  • a heterocycle denotes, for example, morpholinyl, piperidyl, tetrahydrofuryl or pyrrolidinyl.
  • carbocycle means a 4- to 8-membered, preferably 5- or 6-membered, saturated or unsaturated cyclic group, the ring members of which consist of carbon atoms.
  • a carbocycle denotes, for example, a cyclopentyl or cyclohexyl ring.
  • aryl means a fused or nonfused monocyclic or polycyclic carbon-based group comprising from 6 to 22 carbon atoms, and in which at least one ring is aromatic.
  • the aryl radical is a phenyl, biphenyl, naphthyl, anthracenyl or tetrahydronaphthyl, and more preferentially a phenyl.
  • aryl or heterocycle or “carbocycle” group or the aryl or heterocyclic or carbocyclic part of a group may be substituted with at least one substituent borne by a carbon atom, chosen from:
  • halogen atom such as chlorine
  • a (hetero)cyclic group or a nonaromatic part of an aryl group may also be substituted with one or more oxo groups.
  • protecting group for a phenol function means a protecting group such as those described in Greene's Protective Groups in Organic Synthesis, P.G.M. Wutz,
  • a subject of the present invention is a process for treating keratin fibers as described above.
  • the treatment process is a process for caring for and/or repairing keratin fibers.
  • the Applicant has discovered, surprisingly, that the use of carnitine or of a derivative thereof in combination with certain aromatic organic anions bearing a carboxylate, sulfonate or phosphonate group, in the process according to the invention, makes it possible to improve the mechanical strength of keratin fibers, notably by improving the density of bonding between proteins present in the cortex of the fibers, and thus to reduce the breakage thereof, notably during styling or disentangling, such as combing. Moreover, the Applicant has also observed that it was possible to obtain a long-lasting effect notably with satisfactory persistence with respect to shampoo washing.
  • Composition (A) comprises at least one compound of formula (I) as defined above.
  • the compound of formula (I) is a carnitine salt or a salt of a derivative thereof.
  • the cationic portion of the compound of formula (I) is carnitine or a derivative thereof and the anionic portion
  • An of the compound of formula (I) is an aromatic organic anion.
  • An represents an aromatic organic anion chosen from the compounds of formula (II), (III) or (IV) below: in which:
  • a group -O-X in which X represents a hydrogen atom or a protecting group for the phenol function such as an acyl group, in particular an acetyl group; it being understood that two adjacent groups R 6 to R 10 may also form, together with the carbon atoms that bear them, a saturated or unsaturated or aromatic 5- or 6-membered (hetero)cycle;
  • R a , R b , R c , R d , R e and R f represent, independently of each other:
  • a (CrC 6 )alkyl group optionally substituted with one or more identical or different groups chosen from: -OR, -NR’R”, -C(0)0R, -0-C(0)-R, (hetero)cycle, -C(0)-R, -NH-C(0)-R, -C(0)-NH-R, with R, R’ and R” as defined previously, it being understood that the group -NR’R” is other than an -NH2 group;
  • R a and R b may form, together with the carbon atom which bears them, a saturated or unsaturated, 4- to 8-membered, in particular 4- to 6-membered, (hetero)cycle, and more particularly a 5- or 6-membered carbocycle;
  • R a or R b or R c or R d may form with R 6 or R 10 and the carbon atoms that bear them a 4- to 8- membered (hetero)cycle, more particularly a 5- to 6-membered carbocycle;
  • R b and R c represent a single bond or an ethylenic double bond, it being understood that when represents an ethylenic double bond, R b and R c are absent;
  • - p is an integer equal to 0 or 1 ;
  • - r is an integer equal to 0 or 1 ;
  • R 6 to R 10 represent, independently of each other:
  • R 6 to R 10 represent, independently of each other:
  • R a , R b , R c , R d , R e and R f represent, independently of each other:
  • R a , R b , R c , R d , R e and R f represent, independently of each other:
  • Composition (A) may comprise a mixture of compounds of formula (I) comprising different aromatic organic anions An chosen from the compounds of formula (II), (III) or (IV) as defined above.
  • An is chosen from the compounds of formula (lla), (Ilia) or (IVa) below: in which:
  • R 6 to R 10 represent, independently of each other: ⁇ a hydrogen atom
  • a group -O-X in which X represents a hydrogen atom or a protecting group for the phenol function such as an acyl group, in particular an acetyl group; it being understood that two adjacent groups R 6 to R 10 may also form, together with the carbon atoms that bear them, a saturated or unsaturated or aromatic 5- or 6-membered (hetero)cycle;
  • R a and R b represent, independently of each other:
  • a (CrC 6 )alkyl group optionally substituted with one or more identical or different groups chosen from: -OR, -NR’R”, -C(0)0R, -0-C(0)-R, (hetero)cycle, -C(0)-R, -NH-C(0)-R, -C(0)-NH-R, with R, R’ and R” as defined previously, it being understood that the group -NR’R” is other than an -NH2 group;
  • R 11 represents a hydrogen atom, a negative charge, an alkali metal or an alkaline-earth metal, preferably a negative charge.
  • R 6 to R 10 represent, independently of each other:
  • R 6 to R 10 represent, independently of each other:
  • R a and R b represent, independently of each other:
  • R a and R b represent, independently of each other:
  • An is preferably chosen from the compounds of formula (lla) or (Ilia) as defined above, more preferentially from the compounds of formula (lla).
  • An is chosen from the compounds of formula (ll’a), (lll’a) or (IV’a) below: in which:
  • a group -O-X in which X represents a hydrogen atom or a protecting group for the phenol function such as an acyl group, in particular an acetyl group; it being understood that two adjacent groups R 6 to R 10 may also form, together with the carbon atoms that bear them, a saturated or unsaturated or aromatic 5- or 6-membered (hetero)cycle;
  • R 11 represents a hydrogen atom, a negative charge, an alkali metal or an alkaline-earth metal, preferably a negative charge.
  • R 6 to R 10 represent, independently of each other:
  • R 6 to R 10 represent, independently of each other:
  • An is preferably chosen from the compounds of formula (ll’a) or (lll’a) as defined above, more preferentially from the compounds of formula (H’a).
  • An is chosen from the compounds of formula (ll”a), (lll”a) or (IV”a) below:
  • a group -O-X in which X represents a hydrogen atom or a protecting group for the phenol function such as an acyl group, in particular an acetyl group; it being understood that two adjacent groups R 6 to R 10 may also form, together with the carbon atoms that bear them, a saturated or unsaturated or aromatic 5- or 6-membered (hetero)cycle;
  • - R b represents: ⁇ a hydrogen atom; • a (CrC 6 )alkyl group optionally substituted with one or more identical or different groups chosen from: -OR, -NR’R”, -C(0)OR, -0-C(0)-R, (hetero)cycle, -C(0)-R, -NH-C(0)-R, -C(0)-NH-R, with R, R’ and R” as defined previously, it being understood that the group -NR’R” is other than an -NH2 group;
  • R b may form with R 6 or R 10 and the carbon atoms that bear them a 4- to 8-membered (hetero)cycle, more particularly a 5- to 6-membered carbocycle;
  • R 11 represents a hydrogen atom, a negative charge, an alkali metal or an alkaline-earth metal, preferably a negative charge.
  • R 6 to R 10 represent, independently of each other:
  • R 6 to R 10 represent, independently of each other:
  • R b represents: • a hydrogen atom
  • R b may form with R 6 or R 10 and the carbon atoms that bear them a 4- to 8-membered (hetero)cycle, more particularly a 5- to 6-membered carbocycle.
  • R b represents:
  • An is preferably chosen from the compounds of formula (ll”a) or (lll”a) as defined above, more preferentially from the compounds of formula (ll”a).
  • An is chosen from the compounds of formula (Mb), (Nib) or (IVb) below:
  • a group -O-X in which X represents a hydrogen atom or a protecting group for the phenol function such as an acyl group, in particular an acetyl group; it being understood that two adjacent groups R 6 to R 10 may also form, together with the carbon atoms that bear them, a saturated or unsaturated or aromatic 5- or 6-membered (hetero)cycle;
  • R a , R b , R c and R d represent, independently of each other: ⁇ a hydrogen atom; • a (CrC 6 )alkyl group optionally substituted with one or more identical or different groups chosen from: -OR, -NR’R”, -C(0)0R, -0-C(0)-R, (hetero)cycle, -C(0)-R, -NH-C(0)-R, -C(0)-NH-R, with R, R’ and R” as defined previously, it being understood that the group -NR’R” is other than an -NH2 group;
  • R a and R b may form, together with the carbon atom which bears them, a saturated or unsaturated, 4- to 8-membered, in particular 4- to 6-membered, (hetero)cycle, and more particularly a 5- or 6-membered carbocycle;
  • R a or R b or R c or R d may form with R 6 or R 10 and the carbon atoms that bear them a 4- to 8- membered (hetero)cycle, more particularly a 5- to 6-membered carbocycle;
  • R 11 represents a hydrogen atom, a negative charge, an alkali metal or an alkaline-earth metal, preferably a negative charge.
  • R 6 to R 10 represent, independently of each other:
  • R 6 to R 10 represent, independently of each other:
  • R a , R b , R c and R d represent, independently of each other:
  • R a , R b , R c and R d represent, independently of each other:
  • An is preferably chosen from the compounds of formula (Mb) or (lllb) as defined above, more preferentially from the compounds of formula (lib).
  • An is chosen from the compounds of formula (lie), (lllc) or (IVc) below:
  • a group -O-X in which X represents a hydrogen atom or a protecting group for the phenol function such as an acyl group, in particular an acetyl group; it being understood that two adjacent groups R 6 to R 10 may also form, together with the carbon atoms that bear them, a saturated or unsaturated or aromatic 5- or 6-membered (hetero)cycle;
  • - R a and R d represent, independently of each other: ⁇ a hydrogen atom; • a (CrC 6 )alkyl group optionally substituted with one or more identical or different groups chosen from: -OR, -NR’R”, -C(0)0R, -0-C(0)-R, (hetero)cycle, -C(0)-R, -NH-C(0)-R, -C(0)-NH-R, with R, R’ and R” as defined previously, it being understood that the group -NR’R” is other than an -NH2 group;
  • R 11 represents a hydrogen atom, a negative charge, an alkali metal or an alkaline-earth metal, preferably a negative charge.
  • the ethylenic double bond between -CR a and -CR C may be cis or trans.
  • R 6 to R 10 represent, independently of each other:
  • R 6 to R 10 represent, independently of each other:
  • R a and R c represent, independently of each other:
  • R a and R c represent, independently of each other:
  • An is preferably chosen from the compounds of formula (lie) or (lllc) as defined above, more preferentially from the compounds of formula (lie).
  • An is chosen from the compounds of formula (lid), (Mid) or (IVd) below: f!Vd ⁇ in which:
  • a group -O-X in which X represents a hydrogen atom or a protecting group for the phenol function such as an acyl group, in particular an acetyl group; it being understood that two adjacent groups R 6 to R 10 may also form, together with the carbon atoms that bear them, a saturated or unsaturated or aromatic 5- or 6-membered (hetero)cycle;
  • R a , R b , R c , R d , R e and R f represent, independently of each other:
  • a (Ci-C 6 )alkyl group optionally substituted with one or more identical or different groups chosen from: -OR, -NR’R”, -C(0)0R, -0-C(0)-R, (hetero)cycle, -C(0)-R, -NH-C(0)-R, -C(0)-NH-R, with R, R’ and R” as defined previously, it being understood that the group -NR’R” is other than an -NH2 group;
  • a (Ci-C 6 )alkoxy group optionally substituted with one or more identical or different groups chosen from: -OR, -NR’R”, -C(0)0R, -0-C(0)-R, aryl and -CF 3 and/or optionally interrupted with one or more groups or heteroatoms chosen from: O, NR’, CO, S, SO and SO2, with R, R’ and R” as defined previously, it being understood that the group -NR’R” is other than an -NH2 group;
  • R a and R b may form, together with the carbon atom which bears them, a saturated or unsaturated, 4- to 8-membered, in particular 4- to 6-membered, (hetero)cycle, and more particularly a 5- or 6-membered carbocycle;
  • R a or R b or R c or R d may form with R 6 or R 10 and the carbon atoms that bear them a 4- to 8- membered (hetero)cycle, more particularly a 5- to 6-membered carbocycle;
  • R 11 represents a hydrogen atom, a negative charge, an alkali metal or an alkaline-earth metal, preferably a negative charge.
  • R 6 to R 10 represent, independently of each other:
  • R 6 to R 10 represent, independently of each other:
  • R a , R b , R c , R d , R e and R f represent, independently of each other:
  • An is preferably chosen from the compounds of formula (lid) or (Mid) as defined above, more preferentially from the compounds of formula (lid).
  • Composition (A) may comprise a mixture of compounds of formula (I) comprising different aromatic organic anions An chosen from the compounds of formula (ll a ), (II ), (IV a ), (M’ a ), (IM’ a ), (IV’ a ), (M” a ), (IM” a ), (IV” a ), (ll ), (Ml b ), (IV b ), (ll c ), (IIU), (IV C ), (ll d ), (Ml d ) or (IV d ) as defined above.
  • An is chosen from the compounds of formula (II) as defined above or from the compounds of formula (lla) as defined above or from the compounds of formula (M’a) as defined above or from the compounds of formula (M”a) as defined above or from the compounds of formula (Mb) as defined above or from the compounds of formula (lie) as defined above or from the compounds of formula (lid) as defined above.
  • An is chosen from compounds (Mi) to (II 29 ) below:
  • An is chosen from compounds (Mi) to (lln) as defined above. According to an even more preferred embodiment, An is chosen from compound (11 1 ) or (M 2 ) as defined above.
  • R 5 represents an alkali metal, it may be sodium.
  • the compound of formula (I) is a carnitine salt.
  • R 1 , R 2 and R 3 represent a methyl group and R 4 and R 5 represent a hydrogen atom.
  • the cationic portion of the compound of formula (I) is in the form of an optical isomer of L (levorotatory) or D (dextrorotatory) configuration, more preferentially of L configuration.
  • the compound of formula (I) may be obtained by mixing a first composition comprising the cationic portion of the compound of formula (I) optionally in the form of a salt and of a second composition comprising the anionic portion of the compound of formula (I) optionally in the form of a salt.
  • the mixing may be extemporaneous.
  • the compound of formula (I) may be chosen from the compounds of formulae 1 to 29 below, and mixtures thereof:
  • the compound of formula (I) may be chosen from the compounds of formula (I) of formulae 1 to 11 as defined above, and mixtures thereof. More preferentially, the compound of formula (I) may be chosen from the compounds of formula 1 or 2 as defined above, and mixtures thereof.
  • Composition (A) may comprise a total content of compound(s) of formula (I) ranging from 0.1% to 100%, preferably from 0.5% to 50%, more preferentially from 0.5% to 20% and even more preferentially from 1% to 10% by weight, relative to the total weight of composition (A).
  • Composition (A) used in the process according to the present invention is a cosmetic composition, i.e. a composition which comprises a cosmetically acceptable medium, i.e. a medium that is compatible with human keratin fibers.
  • Composition (A) may comprise a solvent chosen from water, ethanol, isopropanol, glycerol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, dipropylene glycol, diethylene glycol, 2-butoxyethanol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, and mixtures thereof.
  • Composition (A) may comprise a solvent chosen from water, C 2 -C 4 alcohols, polyols, polyol ethers, and mixtures thereof. In this case, the compound of formula (I) may be in dissociated form in composition (A).
  • composition (A) may comprise a solvent chosen from water, ethanol, isopropanol, propylene glycol, and mixtures thereof.
  • composition (A) may comprise a solvent chosen from water, ethanol, propylene glycol, and mixtures thereof.
  • composition (A) may advantageously comprise a water/ethanol mixture, preferably a water/ethanol mixture comprising at least 10%, more preferentially at least 20% and even more preferentially at least 30% by weight of ethanol.
  • composition (A) may notably be formulated in the form of a lotion applied to dry keratin fibers, the use of ethanol making it possible to facilitate the wetting of the dry keratin fibers, the drying of the keratin fibers thus treated and also the diffusion of the active agents in the keratin fibers.
  • Composition (A) may also comprise at least one cosmetic ingredient chosen from nonionic, anionic, cationic and amphoteric surfactants, vitamins and provitamins, including panthenol, fillers, dyestuffs, nacreous agents, opacifiers, sequestrants, film-forming polymers, cationic, anionic or neutral polymers, associative polymers, plasticizers, silicones, thickeners, oils, antifoams, moisturizers, emollients, penetrants, fragrances, preserving agents, and mixtures thereof.
  • nonionic, anionic, cationic and amphoteric surfactants including panthenol, fillers, dyestuffs, nacreous agents, opacifiers, sequestrants, film-forming polymers, cationic, anionic or neutral polymers, associative polymers, plasticizers, silicones, thickeners, oils, antifoams, moisturizers, emollients, penetrants
  • composition (A) may be present in usual amounts, which may readily be determined by a person skilled in the art, and which may range, for each ingredient, from 0.01% to 20% by weight relative to the total weight of composition (A). A person skilled in the art will take care to select the ingredients included in composition (A), and also the amounts thereof, so that they do not harm the properties of the composition.
  • composition (A) may be in any presentation form conventionally used for hair application.
  • composition (A) may be in the form of a lotion, a cream, a foam, a gel, a spray or a lacquer.
  • Composition (A) may be used by rinse-off or leave-on application.
  • Composition (A) may be in the form of a shampoo, a mask, a conditioning composition or a pre-shampoo. Composition (A) may also be in the form of a composition to be added to or mixed with, before application, a shampoo, a mask or a conditioning composition.
  • composition (A) may be packaged in a pump-action bottle or in an aerosol container, so as to apply composition (A) in vaporized (lacquer) form or in the form of a mousse.
  • composition (A) preferably comprises at least one propellant. pH of composition (A)
  • Composition (A) may have a pH ranging from 3 to 10, preferably from 4 to 7.
  • the pH may be adjusted using an organic or mineral acid or an organic or mineral base usually used in cosmetics.
  • Composition (A) may be applied to dry or wet keratin fibers, preferably to dry keratin fibers.
  • the bath ratio of composition (A) applied to the keratin fibers may range from 0.1 to 10.
  • bath ratio means the ratio between the total weight of the applied composition (A) and the total weight of keratin fibers to be treated.
  • the process according to the present invention may comprise at least one additional step following on from step i), chosen from steps ii) to iv) below: ii) a step of placing composition (A) on the keratin fibers, preferably for a time of at least 10 seconds, said leave-on step being optionally performed under a hermetic film such as a curlpaper or a plastic film; iii) a step of rinsing and/or washing the keratin fibers; iv) a step of drying the keratin fibers in ambient air or using a heating device.
  • the process may comprise the additional steps ii) and iv) as described above and performed in that order. More preferentially, the process may comprise all of the additional steps ii), iii) and iv) as described above and performed in that order.
  • the leave-on step may have a duration ranging from 10 seconds to 60 minutes, preferably from 30 seconds to 30 minutes.
  • the washing step may be performed, for example, using a shampoo.
  • the temperature of the heating device may range from 45°C to 230°C, preferably from 45°C to 100°C, more preferentially from 50°C to 80°C.
  • a hairdryer, a heating hood, an iron or a heating brush may be used, for example, as heating device.
  • the drying step iv) may also be a combination of drying with air or with a heating device at a temperature ranging from 50°C to 80°C, such as a hairdryer or a heating hood, followed by a step of treating with an iron.
  • composition (A) may, for example, comprise a water/ethanol mixture which comprises at least 10%, preferably at least 20% and more preferentially at least 30% by weight of ethanol. The use of such a mixture can notably facilitate the evaporation of the composition.
  • a subject of the present invention is a composition (A) as defined above, it being understood that the composition does not comprise the compounds of formulae 1 to 4 below:
  • a subject of the present invention is the compounds of formulae 5 to 29 below and mixtures thereof:
  • a subject of the present invention is the cosmetic use of at least one compound (I) as described above, for caring for and/or repairing keratin fibers, preferably for preventing the breakage of keratin fibers. Any of the compounds (I) described above may be used for this purpose.
  • a subject of the present invention is the cosmetic use of a composition (A) as described above, for caring for and/or repairing keratin fibers, preferably for preventing the breakage of keratin fibers.
  • alkaline solubility means the loss of mass of a sample of 100 mg of keratin fibers under the action of a decinormal sodium hydroxide solution for 30 minutes at 65°C.
  • L-Carnitine DL-mandelate was prepared according to the procedure below:
  • L-Carnitine (R)-(-)-mandelate was prepared according to the procedure below:
  • composition 1, 2, 3, 4, 5 or 6 to be tested is then applied onto one of the six locks with a bath ratio of 0.4 (0.4 g of composition per g of hair).
  • the locks are then massaged with the fingers, making circular movements along the entire length of the lock (five times) and the locks are then covered with kitchen film for 5 minutes.
  • the film is removed and the locks are washed.
  • the washing protocol consists in wetting the locks with tap water at 38°C for 10 seconds.
  • Shampoo is applied (0.4 g/g of hair).
  • the locks are massaged for 15 seconds and rinsed thoroughly with water for 20 seconds.
  • the locks are squeezed dry between two fingers, passing the fingers from the roots to the ends twice to remove the excess water. They are combed. They are dried under a hood (60°C, 10 minutes/g of hair). These various steps are repeated to have five applications in total on each of the locks.
  • the protein denaturing temperature of the six locks onto which compositions 1 , 2, 3, 5 or 6 are applied and also of two control locks (an identical lock of untreated damaged hair and an untreated lock of natural hair) are measured by differential scanning calorimetry.
  • the median drop time before breakage is also measured via the Flexabrasion test for the locks treated with compositions 1 , 2, 3, 5 or 6 and the two control locks.
  • the differential scanning calorimetry technique is known to those skilled in the art as a method for quantifying the reinforcement of proteins in the cortex of hair fibers.
  • the principle of the test is to measure the protein denaturing temperature. The higher the protein denaturing temperature, the better the integrity of the proteins of the cortex, which reflects greater resistance to breakage of the fibers (F.-J. Wortmann and H. Deutz, J. Appl. Polym Sci., 48, 137 (1993).
  • the denaturing temperature is directly linked to the bonding density of the keratin proteins present in the cortex.
  • the lower the denaturing temperature the lower the bonding density between the proteins: the disulfide bridges break and the cortex is damaged.
  • a difference of 2°C is acknowledged by a person skilled in the art as a significant difference.
  • the apparatus used for performing the measurements is a Mettler Toledo DSC 3+ Star System machine (temperature range: 30°C-250°C; heating ramp of 10°C/minute). The measurement is performed on six fibers of the lock.
  • the Flexabrasion technique is known to those skilled in the art for the breakage of keratin fibers (references: Flexabrasion: A Method for Evaluating Hair Strength, Cosmetics & Toiletries Journal, June 26, 2009, and Hair Breakage in Normal and Weathered Hair: Focus on the Black Patient, Journal of Investigative Dermatology Symposium Proceedings, Volume 12, Issue 2, December 2007, pages 6-9).
  • the principle of the test is to measure the time taken for hair fibers subjected to a mechanical stress to break (flexure and abrasion).
  • a Flexabrasion machine (Fiberstress model from the company Textechno) is used. A strand of hair is attached to a 20 g weight at one end and the other end is attached to an immobile bar.
  • the strand of hair moves back and forth over a 300 pm stainless steel wire.
  • the movement has an amplitude of 10 mm and a frequency of 0.5 Hz.
  • the detection of breakage is performed by an optical sensor which records the lifetime (drop time before breakage) in seconds, i.e. the time that the hair takes to break.
  • a series of measurements includes 75 hair strands.
  • a difference in drop time of 100 seconds is acknowledged by a person skilled in the art as a significant difference.
  • L-Carnitine is dissolved in water (5 ml_) in a 20 ml_ vial with magnetic stirring.
  • the acid is dissolved in methanol (10 ml_) in a second vial.
  • the methanolic solution of the acid is added dropwise to the aqueous solution of L-carnitine.
  • the reaction medium is stirred until dissolution is complete (about 30 minutes).
  • the magnetic bar is removed from the vial and the solvent is evaporated off under vacuum at 35°C.
  • compositions tested The following compositions were prepared and then tested according to the procedure described below:
  • Eight locks of damaged hair (1 g/20 cm; alkaline solubility of 20) are placed on a laboratory workbench covered with aluminum foil at room temperature (21 °C). Each of the test compositions is then applied onto one of the eight locks with a bath ratio of 0.4 (0.4 g of composition per g of hair). The locks are then massaged with the fingers, making circular movements along the entire length of the lock (five times) and the locks are then left to stand for 5 minutes. The locks are then washed. The washing protocol consists in wetting the locks with tap water at 38°C for 10 seconds. DOP shampoo is applied (0.4 g/g of hair). The locks are massaged for 15 seconds and rinsed thoroughly with water for 20 seconds.
  • the locks are squeezed dry between two fingers, passing the fingers from the roots to the ends twice to remove the excess water. They are combed. They are dried under a hood (60°C, 10 min/g hair). These various steps are repeated to have five applications in total on each of the locks.
  • the eight locks are then treated with a cosmetic straightening treatment (Mizani Butter Blend Sensitive Scalp), which consists in applying 10 g of the straightening formulation with a brush to each lock, and the locks are then left to stand for 10 minutes.
  • the locks are then washed with DOP shampoo.
  • the washing protocol consists in wetting the locks with tap water at 38°C for 10 seconds.
  • DOP shampoo is applied (0.4 g/g of hair).
  • the locks are massaged gently for 15 seconds and rinsed thoroughly with water for 20 seconds. They are dried under a hood (60°C, 10 min/g hair).
  • the eight locks are suspended vertically and then combed 30 times successively, passing the comb over the entire length of the lock in a single motion.
  • the fibers that are broken and separated from the lock are collected and the amount of collected hair strands is then measured using a precision laboratory balance.
  • compositions 1A to 6A comprising compounds 4 to 9 of the invention.

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Abstract

La présente invention concerne un procédé de traitement de fibres de kératine, comprenant l'application d'une composition comprenant au moins un sel de carnitine ou un sel à base de carnitine comprenant un anion organique aromatique, pour le soin et/ou la réparation de fibres de kératine.
PCT/EP2020/086615 2019-12-20 2020-12-17 Procédé de traitement de fibres de kératine à l'aide d'une composition comprenant un sel de carnitine ou un sel à base de carnitine comprenant un anion organique aromatique WO2021122876A1 (fr)

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FRFR1915365 2019-12-20
FR1915365A FR3104969B1 (fr) 2019-12-20 2019-12-20 Procédé de traitement des fibres kératiniques mettant en œuvre une composition comprenant un sel de carnitine ou de dérivé de carnitine comprenant un anion organique aromatique

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FR3136979A1 (fr) * 2022-06-22 2023-12-29 L'oreal Procédé de traitement des fibres kératiniques mettant en œuvre un sel de carnitine ou de dérivé de carnitine

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59231048A (ja) * 1983-06-11 1984-12-25 Hamari Yakuhin Kogyo Kk ｌ（−）―カルニチンの製造法
EP0688555A2 (fr) * 1994-06-20 1995-12-27 Tanabe Seiyaku Co., Ltd. Agent pour la croissance des cheveux
DE19539859A1 (de) 1995-10-26 1997-04-30 Eugen Konrad Haar und Hautbehandlungsmittel
EP0978272A1 (fr) 1998-08-07 2000-02-09 Kao Corporation Préparation pour les soins de la medulla
EP1800654A2 (fr) 2005-12-23 2007-06-27 Henkel Kommanditgesellschaft auf Aktien Réduction des signes de vieillesse des cheveux
EP2111852A2 (fr) 2008-04-21 2009-10-28 Henkel AG & Co. KGaA Procédé de traitement pour le soin des cheveux
CN102727481A (zh) * 2010-06-29 2012-10-17 辽宁思百得医药科技有限公司 包含左卡尼汀和羟苯磺酸盐的药物组合物
US20130266529A1 (en) * 2010-11-25 2013-10-10 L'oreal Process for stripping keratin fibres using a composition comprising a sulfinic acid derivative and an acidic aqueous composition
WO2019074129A1 (fr) * 2017-10-12 2019-04-18 L'oreal Procédé de remodelage de fibres kératiniques
WO2019200027A1 (fr) * 2018-04-12 2019-10-17 Lubrizol Advanced Materials, Inc. Composition de modification capillaire et procédé associé

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59231048A (ja) * 1983-06-11 1984-12-25 Hamari Yakuhin Kogyo Kk ｌ（−）―カルニチンの製造法
EP0688555A2 (fr) * 1994-06-20 1995-12-27 Tanabe Seiyaku Co., Ltd. Agent pour la croissance des cheveux
DE19539859A1 (de) 1995-10-26 1997-04-30 Eugen Konrad Haar und Hautbehandlungsmittel
EP0978272A1 (fr) 1998-08-07 2000-02-09 Kao Corporation Préparation pour les soins de la medulla
EP1800654A2 (fr) 2005-12-23 2007-06-27 Henkel Kommanditgesellschaft auf Aktien Réduction des signes de vieillesse des cheveux
EP2111852A2 (fr) 2008-04-21 2009-10-28 Henkel AG & Co. KGaA Procédé de traitement pour le soin des cheveux
CN102727481A (zh) * 2010-06-29 2012-10-17 辽宁思百得医药科技有限公司 包含左卡尼汀和羟苯磺酸盐的药物组合物
US20130266529A1 (en) * 2010-11-25 2013-10-10 L'oreal Process for stripping keratin fibres using a composition comprising a sulfinic acid derivative and an acidic aqueous composition
WO2019074129A1 (fr) * 2017-10-12 2019-04-18 L'oreal Procédé de remodelage de fibres kératiniques
WO2019200027A1 (fr) * 2018-04-12 2019-10-17 Lubrizol Advanced Materials, Inc. Composition de modification capillaire et procédé associé

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
"Flexabrasion: A Method for Evaluating Hair Strength", COSMETICS & TOILETRIES JOURNAL, 26 June 2009 (2009-06-26)
"Hair Breakage in Normal and Weathered Hair: Focus on the Black Patient", JOURNAL OF INVESTIGATIVE DERMATOLOGY SYMPOSIUM PROCEEDINGS, vol. 12, December 2007 (2007-12-01), pages 6 - 9
F.-J. WORTMANNH. DEUTZ, J. APPL. POLYM SCI., vol. 48, 1993, pages 137

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