WO2018115394A1 - Procédé de défrisage et/ou de lissage de fibres kératiniques faisant appel à des agents réducteurs et à des composés disulfures cationiques, et kit de lissage - Google Patents

Procédé de défrisage et/ou de lissage de fibres kératiniques faisant appel à des agents réducteurs et à des composés disulfures cationiques, et kit de lissage Download PDF

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WO2018115394A1
WO2018115394A1 PCT/EP2017/084298 EP2017084298W WO2018115394A1 WO 2018115394 A1 WO2018115394 A1 WO 2018115394A1 EP 2017084298 W EP2017084298 W EP 2017084298W WO 2018115394 A1 WO2018115394 A1 WO 2018115394A1
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radical
optionally substituted
thiol
group
process according
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PCT/EP2017/084298
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English (en)
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Virginie BURCKBUCHLER
Henri Samain
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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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • 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
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • 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
    • A61Q5/04—Preparations for permanent waving or straightening the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/884—Sequential application

Definitions

  • the present invention relates to a process for curl-relaxing and/or straightening keratin fibres, such as the hair, which comprises the application to the fibres of one or more compositions comprising reducing agents, one or more compositions comprising cationic disulfide compounds and a step of heat treatment of the fibres by means of a heating tool.
  • the invention also relates to the composition(s) comprising reducing agents and the composition(s) comprising cationic disulfide compounds and the use thereof in a process for curl-relaxing and/or straightening keratin fibres.
  • the invention relates to a multi-compartment device or "kit” that is suitable for performing such a process.
  • the technique most commonly used consists, in a first stage, in opening the -S-S- disulfide bonds of keratin (keratocystine) generally by means of a basic composition containing a sulfur-based reducing agent (reduction step), and then, after having rinsed the head of hair thus treated, generally with water, in reconstituting, in a second stage, said disulfide bonds by applying to the hair, which has been placed under tension beforehand, an oxidizing composition (oxidation step, also known as the fixing step) so as finally to give the hair the desired shape.
  • oxidizing composition oxidation step, also known as the fixing step
  • the new shape given to the hair by such a chemical treatment is eminently long-lasting and especially withstands washing with water or shampoos, as opposed to the simple standard techniques of temporary reshaping, such as hairsetting.
  • the products intended for straightening or uncurling are generally formulated either using very alkaline compositions, with a pH above 12, or using a high concentration of thiols, such as mercaptan compounds.
  • the oxidizing compositions required for performing the fixing step are usually compositions based on aqueous hydrogen peroxide solution.
  • the reducing agents are generally used in high concentrations, which may lead to more or less pronounced degradation of the keratin fibre, in particular when the hair is dyed.
  • These drawbacks are observed in particular with thioglycolic acid which is generally used in basic medium with pH values ranging from 8.5 to 9.5.
  • this process must retain good performance qualities in terms of the straightening of keratin fibres, in particular with an effect that is persistent on shampooing several times. Furthermore, it is desirable for these treatments to be easy to apply, and comfortable for the operator to use, in particular in terms of odours deriving from the use of such a process.
  • steps i) and ii) are performed separately i) then ii) or else ii) then i).
  • the steps of the process are performed in the following order: i) then ii) then iii). This process makes it possible to achieve the desired properties, inter alia in terms of integrity, quality and cosmeticity of the keratin fibres, while at the same time obtaining curl relaxation and/or straightening of keratin fibres that is of good quality and long-lasting.
  • One subject of the present invention is thus a process for curl-relaxing and/or straightening keratin fibres, in particular keratin fibres such as the hair, comprising steps i), ii) and iii) as defined previously.
  • the implementation of this process makes it possible to obtain curl relaxation and/or straightening of keratin fibres that is of good quality and persistent on shampooing several times. Furthermore, the implementation of this process makes it possible to provide the keratin fibres with good cosmetic properties, in particular sheen and a soft feel.
  • the process according to the invention is a process for straightening keratin fibres, in particular the hair.
  • a subject of the invention is also a kit that is suitable for performing the process of the invention.
  • This kit comprises at least two compartments:
  • a first compartment comprising an acidic composition (A), preferably at a pH between 1 and 5 inclusive, which comprises one or more thiol-based reducing agents; - a second compartment comprising a composition (B) which comprises one or more cationic disulfide compounds and
  • a third compartment comprising a composition (C) which comprises one or more non-thiol-based reducing agents.
  • pH between 1 and 5 inclusive means that the limits 1 and 5 are included in the pH range.
  • a subject of the present invention is also the use of compositions (A) and (B) in a process for shaping, curl-relaxing and/or straightening keratin fibres, especially human keratin fibres such as the hair.
  • performing this process makes it possible to obtain curl relaxation and/or a reduction of the volume of the head of hair that is gradual.
  • Keratin fibres, especially hair, treated via the process according to the invention have a softer feel and remain tamed. No frizziness is observed.
  • the keratin fibres are aligned, straight and disentangle easily, which makes them easier to comb.
  • the process according to the invention makes it possible to substantially reduce the unpleasant odours derived from performing a standard curl relaxation and/or straightening process.
  • the "aryl” or “heteroaryl” radicals or the aryl or heteroaryl part of a radical may be substituted with at least one substituent borne by a carbon atom, chosen from: a Ci-C 6 and preferably C1-C4 alkyl radical optionally substituted with one or more radicals chosen from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, acylamino, amino substituted with two C1-C4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl group, or the two radicals possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- to 7-membered and preferably 5- or 6-membered heterocycle optionally comprising another nitrogen or non-nitrogen heteroatom;
  • Ci-C 6 alkoxy or Ci-C 6 alkylthio radical a Ci-C 6 alkoxy or Ci-C 6 alkylthio radical
  • a 5- or 6-membered heterocycloalkyl radical preferentially morpholino, piperazino, piperidino or pyrolidino, which is optionally substituted with a (C1-C4) alkyl radical, preferentially methyl;
  • a 5- or 6-membered heteroaryl radical preferentially imidazolyl, optionally substituted with a (Ci-C4)alkyl radical, preferentially methyl;
  • alkyl radicals possibly forming with the nitrogen atom to which they are attached a saturated or unsaturated, optionally substituted 5- to 7-membered heterocycle, optionally comprising at least one other nitrogen or non-nitrogen heteroatom,
  • an acylamino radical (-N(R)-C(0)-R) in which the R radical is a hydrogen atom or a C1-C4 alkyl radical optionally bearing at least one hydroxyl group and the R' radical is a C1-C2 alkyl radical;
  • R radicals which may be identical or different, represent a hydrogen atom or a C1-C4 alkyl radical optionally bearing at least one hydroxyl group;
  • R'-S(0) 2 -N(R)- an alkylsulfonylamino radical in which the R radical represents a hydrogen atom or a C1-C4 alkyl radical optionally bearing at least one hydroxyl group and the R' radical represents a C1-C4 alkyl radical, or a phenyl radical;
  • R radicals (R) 2 N-S(0) 2 -) in which the R radicals, which may be identical or different, represent a hydrogen atom or a C1-C4 alkyl radical optionally bearing at least one hydroxyl group;
  • a carboxyl radical in the acid or salified form preferably salified with an alkali metal or a substituted or unsubstituted ammonium
  • cyclic or heterocyclic part of a non-aromatic radical may be substituted with at least one substituent chosen from the following groups:
  • alkylcarbonylamino (R-C(O)-N(R')-) in which the radical R' is a hydrogen atom or a C1-C4 alkyl radical optionally bearing at least one hydroxyl group, and the radical R is a C1-C2 alkyl radical or an amino radical optionally substituted with one or two C1-C4 alkyl groups, which may be identical or different, themselves optionally bearing at least one hydroxyl group, said alkyl radicals possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- to 7-membered heterocycle optionally comprising at least one other nitrogen or non-nitrogen heteroatom;
  • R-C(O)-O- in which the radical R is a C1-C4 alkyl radical or an amino group optionally substituted with one or two identical or different C1-C4 alkyl groups themselves optionally bearing at least one hydroxyl group, said alkyl radicals possibly forming with the nitrogen atom to which they are attached a saturated or unsaturated, optionally substituted 5- to 7-membered heterocycle, optionally comprising at least one other nitrogen or non-nitrogen heteroatom;
  • alkoxycarbonyl in which the radical R is a C1-C4 alkoxy radical, X is an oxygen atom or an amino group optionally substituted with a C1-C4 alkyl group itself optionally bearing at least one hydroxyl group, said alkyl radical possibly forming with the nitrogen atom to which it is attached a saturated or unsaturated, optionally substituted 5- to 7-membered heterocycle, optionally comprising at least one other nitrogen or non- nitrogen heteroatom;
  • a cyclic or heterocyclic radical, or a non-aromatic part of an aryl or heteroaryl radical may also be substituted with one or more oxo groups;
  • a hydrocarbon-based chain is unsaturated when it comprises one or more double bonds and/or one or more triple bonds;
  • an "aryl” radical represents a monocyclic or fused or non-fused polycyclic carbon- based group, comprising from 6 to 22 carbon atoms, at least one ring of which is aromatic; preferentially, the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl or tetrahydronaphthyl;
  • a heteroaryl radical represents a fused or non- fused, optionally cationic, 5- to 22- membered monocyclic or polycyclic group, comprising from 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium atoms, and at least one ring of which is aromatic; preferentially, a heteroaryl radical is chosen from acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridyl, tetrazolyl, dihydrothiazolyl, imidazopyridyl, imidazolyl, indolyl, isoquinolyl, naphthoimidazolyl, naphthooxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolyl
  • heterocyclic radical is a fused or non-fused, 5- to 22-membered monocyclic or polycyclic radical, possibly containing one or two unsaturations but non-aromatic, comprising from 1 to 6 heteroatoms chosen from nitrogen, oxygen, sulfur and selenium atoms;
  • an “alkyl” radical is a linear or branched, saturated Ci-Cio, in particular Ci-Cs, more particularly Ci-C 6 and preferably C1-C4, hydrocarbon-based radical;
  • an alkoxy" radical is an "alkyl-oxy" radical in which the alkyl group is as defined previously;
  • an “alkenyl” radical is a linear or branched C2-C10, in particular C2-C8, more particularly C2-C6, preferably C2-C4, hydrocarbon-based radical comprising one or more conjugated or non-conjugated unsaturations, preferably comprising one or two double bonds, such as ethylenyl;
  • alkyl or alkenyl radical may be substituted with one or more radicals chosen from the following radicals: i) hydroxyl, ii) C1-C4 alkoxy, iii) acylamino, iv) amino optionally substituted with one or two identical or different C1-C4 alkyl radicals, said alkyl radicals possibly forming, with the nitrogen atom that bears them, a 5- to 7-membered heterocycle, optionally comprising another nitrogen or non-nitrogen heteroatom; v) carboxy; or vi) aryl such as phenyl optionally substituted with one or more (di)(Ci-C4)(alkyl)amino groups or hydroxyl groups;
  • an "alkoxy" radical is an alkyl-oxy radical for which the alkyl radical is a linear or branched Ci-Cs and preferentially Ci-C 6 hydrocarbon-based radical;
  • alkoxy group when the alkoxy group is optionally substituted, this implies that the alkyl group is optionally substituted as defined above;
  • organic or mineral acid salt is more particularly intended to mean salts chosen from a salt derived from i) hydrochloric acid HC1, ii) hydrobromic acid HBr, iii) sulfuric acid H2SO4, iv) alkylsulfonic acids: Alk-S(0) 2 OH such as methanesulfonic acid and ethanesulfonic acid; v) arylsulfonic acids: Ar-S(0) 2 OH such as benzenesulfonic acid and toluenesulfonic acid; vi) citric acid; vii) succinic acid; viii) tartaric acid; ix) lactic acid; x) alkoxysulfinic acids: Alk-0-S(0)-OH such as methoxysulfinic acid and ethoxy sulfuric acid; xi) aryloxy sulfuric acids such as tolueneoxysulfinic acid and phenoxysulfmic acid; xii) phosphoric acid,
  • anionic counterion means an anion or an anionic group derived from an organic or mineral acid which counterbalances the cationic charge of the dye; more particularly, the anionic counterion is chosen from: i) halides such as chloride or bromide; ii) nitrates; iii) sulfonates, including Ci-C 6 alkylsulfo nates: Alk-S(0) 2 0 " such as methylsulfonate or mesylate and ethylsulfonate; iv) arylsulfo nates: Ar-S(0) 2 0 " such as benzenesulfonate and toluenesulfonate or tosylate; v) carboxylates Alk-C(0)-OH with Alk representing a (Ci-C 6 )alkyl group optionally substituted with one or more hydroxyl or carboxylate groups such as citrate; vi) succinate; vii) tartrate
  • the process according to the invention uses i) at least one thiol-based reducing agent and ii) at least one organic solvent, it being understood that the composition(s) containing said thiol-based reducing agent(s) are acidic; preferably said composition(s) have a pH between 1 and 5 inclusive, preferably between 2.5 and 4 inclusive.
  • the thiol-based reducing agent(s) present in composition (A) used according to the invention are chosen from organic compounds comprising one or more mercapto (-SH or -S-) groups, or disulfide (-S-S-) groups, preferably -SH groups and at least one other function chosen from carboxylic acid, amine, amide, ester and alcohol functions, and mixtures thereof.
  • the reducing agent(s) used in the invention are chosen from those of formulae i-l and i-2, and also the organic or mineral acid or base salts thereof, optical isomers thereof and tautomers thereof, and the solvates such as hydrates:
  • R represents a group from among:
  • R' " represents a hydrogen atom or a linear or branched (Ci-C4)alkyl group, C(O) or combinations thereof such as -O-C(O)-, -C(0)-0- -N(R" ')-C(0)- or -C(0)-N(R” ')-; (hetero)aryl optionally substituted in particular with one or more hydroxyl, thiol or carboxy groups;
  • R and R which may be identical or different, represent a (Ci-C8)alkyl group, preferably (Ci-C6)alkyl group, substituted with one or more groups chosen from hydroxyl, thiol and carboxy; or else R' and R" form, together with the sulfur atom which bears them, a 5- to 7-membered heterocyclic group, which is preferably saturated, which comprises from 1 to 3 heteroatoms, and which is optionally substituted (in particular with one or more (Ci-C6)alkyl groups optionally substituted with one or more hydroxyl, thiol or carboxy groups), more preferentially the heterocyclic group is a dithiolane group optionally substituted with a (Ci-C6)alkyl group optionally substituted with one or more carboxy groups.
  • the reducing agents are of formula i-1, in particular those for which R represents a linear or branched (Ci- C8)alkyl group, preferably (Ci-C6)alkyl group, substituted with one or more groups chosen from carboxyl C(0)OH, amino, hydroxyl -OH, and thiol -SH;
  • R represents a linear or branched, uninterrupted (Ci-Cs)alkyl group, preferably (Ci-C 6 )alkyl group.
  • the reducing agents are of formula i-1 for which R represents:
  • - a 5- to 10-membered and preferably 9- or 10-membered bicyclic heteroaryl, comprising from 1 to 4 heteroatoms chosen from O, S or N, preferably N, optionally substituted with one or more hydroxyl or thiol groups.
  • the reducing agents are of formula i-2, in particular those for which R' and R", which may be identical or different, represent a (Ci-C8)alkyl group, preferably (Ci-C6)alkyl group, substituted with one or more groups chosen from hydroxyl, thiol and carboxy.
  • the reducing agents are of formula i-2, in particular those for which R' and R" form, together with the sulfur atom which bears them, a 5- to 7-membered heterocyclic group, which is preferably saturated, which comprises from 1 to 3 heteroatoms, and which is optionally substituted with one or more (Ci-C6)alkyl groups optionally substituted with one or more hydroxyl, thiol or carboxy groups, more preferentially the heterocyclic group is a dithiolane group optionally substituted with a (Ci-C6)alkyl group optionally substituted with one or more hydroxyl, thiol or carboxy groups.
  • the reducing agent(s) comprising at least one mercapto or disulfide group of the invention are chosen from thioglycolic acid, thiolactic acid or 2- mercaptopropionic acid, cysteine, cysteamine, homocysteine, glutathione, thioglycerol, thiomalic acid, 3 -mercaptopropionic acid, thiodiglycol, 2- mercaptoethanol, dithiothreitol, thioxanthine, thiosalicylic acid, thio digly colic acid, lipoic acid, N-acetylcysteine, and thioglycolic or thiolactic acid esters and amides, in particular glyceryl mo no thioglycolate, and mixtures of these compounds.
  • the thiol-based reducing agent(s) as defined previously may be used especially in the form of salts, in particular alkali metal salts such as sodium and potassium salts, alkaline-earth metal salts, for example magnesium and calcium salts, ammonium salts, amine salts and amino alcohol salts. Ammonium thioglycolate may thus be used as thiol.
  • the thiol-based reducing agent(s) are chosen from thioglycolic acid and salts thereof, thiolactic acid and salts thereof, cysteamine and salts thereof, and mixtures thereof.
  • the thiol-based reducing agent(s) are chosen from thioglycolic acid and thiolactic acid.
  • composition (A) according to the invention are preferably present in an amount ranging from 0.02% to 15% by weight, preferably from 0.1% to 10%, and even more preferentially from 0.5% to 2% by weight, relative to the total weight of said composition.
  • composition (A) and/or (B) according to the invention may be adjusted to the desired value by means of basifying agents or acidifying agents that are usually used.
  • the organic alkaline agent(s) are preferably chosen from alkanolamines, in particular mono-, di- or tri- hydroxy(Ci-C6)alkylamines, such as triethanolamine, oxyethylenated and/or oxypropylenated ethylenediamines, amino acids, the polyamines of formula (VIII) below, and mixtures thereof:
  • W is a divalent Ci-C 6 alkylene radical optionally substituted with one or more hydroxyl groups or a Ci-C 6 alkyl radical, and/or optionally interrupted with one or more heteroatoms such as O, or NR U ;
  • R x , R y , R z , Rt and R u which may be identical or different, represent a hydrogen atom or a Ci-C 6 alkyl, Ci-C 6 hydroxyalkyl or Ci-C 6 amino alkyl radical.
  • amines of formula (VIII) examples include 1 ,3- diaminopropane, l ,3-diamino-2-propanol, spermine and spermidine.
  • alkanolamine means an organic amine comprising a primary, secondary or tertiary amine function, and one or more linear or branched Ci to Cs alkyl groups bearing one or more hydroxyl radicals.
  • Organic amines chosen from alkanolamines such as monoalkanolamines, dialkanolamines or trialkanolamines comprising one to three identical or different Ci to C 4 hydroxyalkyl radicals are in particular suitable for use in the invention.
  • MAA monoethanolamine
  • diethanolamine triethanolamine
  • monoisopropanolamine diisopropanolamine
  • ⁇ , ⁇ -dimethylethanolamine 2-amino-2-methyl- 1 -propanol
  • triisopropanolamine 2-amino-2-methyl-l ,3-propanediol
  • 3-amino-l ,2-propanediol 3- dimethylamino- 1 ,2-propanediol and tris(hydroxymethyl)aminomethane.
  • amino acids that may be used are of natural or synthetic origin, in their L, D or racemic form, and comprise at least one acid function chosen more particularly from carboxylic acid, sulfonic acid, phosphonic acid and phosphoric acid functions.
  • the amino acids may be in neutral or ionic form.
  • basifying agents mention may more particularly be made of aqueous ammonia, alkanolamines, and mineral or organic hydroxides.
  • HC1 ii) hydrobromic acid HBr, iii) sulfuric acid H 2 S0 4 , iv) alkylsulfonic acids: Alk- S(0) 2 OH, such as methanesulfonic acid and ethanesulfonic acid; v) arylsulfonic acids: Ar-S(0) 2 OH, such as benzenesulfonic acid and toluenesulfonic acid; vi) (poly)hydroxylated carboxylic acids, such as citric acid, succinic acid, tartaric acid or lactic acid, vii) alkoxysulfmic acids: Alk-0-S(0)-OH, such as methoxysulfinic acid and ethoxysulfinic acid; viii) aryloxysulfinic acids, such as tolueneoxysulfinic acid and phenoxysulfinic acid; ix) phosphoric acid H3PO4; x) acetic acid CH3C(0)-OH
  • the cationic disulfide compound(s) are chosen from the compounds of formula (I):
  • R 1 denotes a hydrocarbon-based group of formula chosen from
  • R 2 , R 3 denote, independently of each other, a linear hydrocarbon-based group containing from 1 to 6 carbon atoms or a branched hydrocarbon-based group containing from 3 to 6 carbon atoms, which is saturated or unsaturated, preferably saturated, optionally substituted with one or more hydroxyl groups;
  • R 4 denotes a hydrogen atom or a (Ci-C 6 )alkyl group, preferably a hydrogen atom;
  • ⁇ x is an integer ranging from 1 to 20;
  • m is an integer ranging from 1 to 20;
  • n is an integer ranging from 1 to 20;
  • X which may be identical or different, denote an anionic counterion; ⁇ Y represents an oxygen or sulfur atom or a group N(R 5 ) with R 5 denoting a hydrogen atom or a (Ci-C 6 )alkyl group; preferably, Y represents an oxygen atom.
  • the compounds of formula (I) are such that R 1 denotes a hydrocarbon-based group from among: i) methyl,
  • the compounds of formula (I) are such that R 1 denotes a hydrocarbon-based group:
  • the compounds of formula (I) are such that R 1 denotes a hydrocarbon-based group containing from 15 to 19 carbon atoms, i.e. in which m is an integer between 13 and 17 inclusive (13 ⁇ m ⁇ 17).
  • the compounds of formula (I) are such that the sum of n+m is between 12 and 22 inclusive, preferably between 14 and 18 inclusive.
  • the compounds of formula (I) are such that x is an integer between 1 and 4 inclusive, and preferably x is equal to 1.
  • the compounds of formula (I) are such that R 2 and R 3 represent, independently of each other, a linear hydrocarbon-based group containing from 1 to 6 and preferably from 1 to 4 carbon atoms or a branched hydrocarbon-based group containing from 3 to 6 and preferably 3 or 4 carbon atoms, which is unsubstituted.
  • R 2 and R 3 denote a linear or branched (Ci-C6)alkyl and more preferentially (Ci-C4)alkyl group such as methyl, ethyl or isobutyl, even more preferentially methyl.
  • the compounds of formula (I) are such that R 4 represents a hydrogen atom.
  • the compounds of formula (I) are such that Y represents an oxygen or sulfur atom, preferably oxygen.
  • the compounds of formula (I) are such that X " denotes an anionic counterion chosen from halide ions, in particular chloride or bromide, sulfate, phosphates, R"-C(0)-0 " with R' ' denoting an optionally hydroxylated C1-C5 hydrocarbon-based radical, in particular acetate, lactate, citrate, (Ci-C4)alkyl sulfates, (Ci-C4)alkylaryl-sulfonates, mesylate, tosylate and triflate, and preferentially, X " denotes a halide anionic counterion such as chloride or bromide.
  • the compounds of formula (I) are chosen from:
  • compound (I) of the invention is compound 15.
  • the compounds of formula (I) are synthesized from reagents that are accessible either commercially or synthesized via standard methods known to those skilled in the art. Mention may be made, for example, of the book by J. March, Advanced Organic Chemistry, Reactions, Mechanisms and Structure, fourth edition, 1992.
  • the compound(s) of formula (I) are present in a content ranging from 0.5% to 30% by weight relative to the total weight of the composition, preferably ranging from 1% to 20% by weight, more preferentially ranging from 2% to 15%, for instance 10% by weight, relative to the total weight of composition (B) containing them.
  • the process according to the invention preferably comprises a step o) of using a composition (C) containing one or more non-thiol-based reducing agents after step i) and/or ii) and before the heat treatment step iii).
  • the non-thiol-based reducing agent(s) present in composition (C) according to the invention are chosen from ortho-diphenol derivatives with reducing properties.
  • ortho-diphenol denotes compounds comprising at least one aromatic ring, preferably a benzene ring, comprising at least two hydroxyl (OH) groups borne by two adjacent carbon atoms of the aromatic ring which in addition do not comprise a mercapto or disulfide group.
  • the aromatic ring may more particularly be a fused aryl or fused heteroaromatic ring, i.e. optionally comprising one or more heteroatoms, such as benzene, naphthalene, tetrahydronaphthalene, indane, indene, anthracene, phenanthrene, isoindole, indoline, isoindoline, benzofuran, dihydrobenzofuran, chroman, isochroman, chromene, isochromene, quinoline, tetrahydroquinoline and isoquinoline, said aromatic ring comprising at least two hydroxyl groups borne by two adjacent carbon atoms of the aromatic ring.
  • the aromatic ring of the ortho-diphenol derivatives according to the invention is a benzene ring.
  • fused ring means that at least two saturated or unsaturated and heterocyclic or non-heterocyclic rings have a common bond, i.e. that at least one ring is joined side by side with another ring.
  • the ortho-diphenols according to the invention may or may not be salified. They may also be in aglycone form (without bonded sugars) or in the form of glycosylated compounds.
  • the ortho-diphenol derivative represents a compound of formula (II), or an oligomer thereof, in salified or non-salified form:
  • Ri to R 4 which may be identical or different, represent:
  • a saturated or unsaturated heterocyclic radical carrying or not carrying a cationic or anionic charge, optionally substituted and/or optionally fused with an aromatic ring, preferably a benzene ring, said aromatic ring being optionally substituted, in particular with one or more hydroxyl or glycosyloxy groups,
  • Ri - R 2 , R 2 - R3 or R3 - R 4 form, together with the carbon atoms carrying them, a saturated or unsaturated and aromatic or non-aromatic ring, optionally comprising one or more heteroatoms and optionally fused with one or more saturated or unsaturated rings optionally comprising one or more heteroatoms.
  • Ri to R 4 together form from one to four rings.
  • a specific embodiment of the invention relates to ortho-diphenol derivatives of formula (II), two adjacent substituents Ri - R 2 , R 2 - R3 or R3 - R 4 of which cannot form, with the carbon atoms which carry them, a pyrrolyl radical. More particularly, R 2 and R3 cannot form a pyrrolyl radical fused to the benzene ring bearing the two hydroxy Is.
  • the ortho-diphenols of use in the process of the invention can be natural or synthetic.
  • the natural ortho-diphenols include the compounds which may be present in nature and which are reproduced by chemical (semi)synthesis.
  • the salts of the ortho-diphenols of the invention can be salts of acids or of bases.
  • the acids may be mineral or organic.
  • the acid is hydrochloric acid, which results in chlorides.
  • the bases may be mineral or organic.
  • the bases are alkaline hydroxides, such as sodium hydroxide, which results in sodium salts.
  • composition(s) comprise as ingredient one or more synthetic ortho-diphenol derivatives that do not exist in nature.
  • the process for curl-relaxing and/or straightening keratin fibres uses, as non-thiol-based agent, one or more natural ortho-diphenol derivatives.
  • ortho-diphenols that may be used in the process of the invention are in particular:
  • anthocyanidins such as cyanidin, delphinidin or petunidin
  • anthocyanins or anthocyans for instance myrtillin
  • hydroxystilbenes for example 3,3',4,5'-tetrahydroxystilbene, optionally oxylated (for example glucosylated),
  • proanthocyanidins and especially the proanthocyanidins Al, A2, Bl, B2, B3 and CI,
  • the two forms may be used in the compositions according to the invention, as may the racemic mixtures.
  • the natural ortho-diphenols result from extracts of animals, bacteria, fungi, algae or plants, used in their entirety or partially.
  • the extracts are derived from plants or plant parts, such as fruit, including citrus fruit, vegetables, trees or shrubs. Use may also be made of mixtures of these extracts, which are rich in ortho-diphenols as defined above.
  • the natural ortho-diphenols of the invention are derived from plants or plant parts.
  • the extracts are obtained by extraction of various plant parts, for instance the root, the wood, the bark, the leaf, the flower, the fruit, the seed, the pod or the peel.
  • the ortho-diphenol derivative(s) are natural extracts rich in ortho-diphenols. According to a preferred form, the ortho-diphenol derivative(s) are solely natural extracts.
  • the natural extracts according to the invention may be in the form of powders or liquids.
  • the extracts of the invention are provided in the form of powders.
  • the non-thiol-based reducing agent(s) present in composition (C) according to the invention are chosen from meta-hydroxyphenol derivatives, also known as resorcinols, with reducing properties.
  • resorcinols denotes compounds which comprise at least one aromatic ring, preferably a benzene ring, comprising at least two hydroxyl (OH) groups borne by two carbon atoms which are in the meta position relative to each other, and which also do not comprise any mercapto or disulfide groups.
  • the aromatic ring may more particularly be a fused aryl or fused heteroaromatic ring, i.e. optionally comprising one or more heteroatoms, such as benzene, naphthalene, tetrahydronaphthalene, indane, indene, anthracene, phenanthrene, isoindole, indoline, isoindoline, benzofuran, dihydrobenzofuran, chroman, isochroman, chromene, isochromene, quinoline, tetrahydroquinoline and isoquinoline, said aromatic ring comprising at least two hydroxyl groups borne by two carbon atoms which are in the meta position relative to each other.
  • the aromatic ring of the resorcinol derivatives according to the invention is a benzene ring.
  • the non-thiol- based reducing agent(s) present in the composition(s) used according to the invention are chosen from the meta-hydroxyphenol derivatives of formula (III), and also the organic or mineral acid or base salts thereof, and the solvates thereof such as hydrates:
  • Ri, P 2 and R 4 which may be identical or different, represent:
  • a saturated or unsaturated heterocyclic radical optionally bearing a cationic or anionic charge, optionally substituted and/or optionally fused with an aromatic ring, preferably a benzene ring, said aromatic ring being optionally substituted, in particular with one or more hydroxyl or glycosyloxy groups,
  • - a saturated or unsaturated heterocyclic radical optionally bearing a cationic or anionic charge, optionally substituted and/or optionally fused with an aromatic ring, preferably a benzene ring, said aromatic ring being optionally substituted, in particular with one or more hydroxyl or glycosyloxy groups, - a radical containing one or more silicon atoms,
  • R 2 - R3 or R3 - R4 form, together with the carbon atoms bearing them, a saturated or unsaturated, non-aromatic ring, optionally containing one or more heteroatoms and optionally fused with one or more saturated or unsaturated rings optionally containing one or more heteroatoms.
  • R 2 to R 4 together form from two to four rings.
  • non-thiol-based reducing agent(s) present in composition (C) according to the invention are chosen from the meta-hydroxyphenols of formula (III) in which the substituents:
  • Ri, R3 and R 4 which may be identical or different, represent:
  • ⁇ R 2 represents:
  • the substituent R 2 in formula (III) represents a hydrogen atom or a (Ci-C 6 )alkyl group, preferably a hydrogen atom.
  • the non-thiol-based reducing agent(s) present in the composition (C) according to the invention are chosen from the resorcinol derivatives of formula (III), and also the organic or mineral acid or base salts thereof, and the solvates thereof such as hydrates:
  • R 1 to R 4 which may be identical or different, represent a hydrogen or halogen atom, or a group chosen from:
  • M + representing a cationic counterion such as an alkali metal or alkaline-earth metal, or an ammonium
  • amido -C(0)-NR 6 R 7 or -NR 6 -C(0)-R 7 with R 6 and R 7 which may be identical or different, representing a hydrogen atom or a (Ci-Cio)alkyl group, particularly - C(0)-NH 2 ;
  • R 8 and R 9 which may be identical or different, representing a hydrogen atom or a (Ci-Cio)alkyl group, particularly -NH 2 .
  • Ri, R 2 and R 4 represent a hydrogen atom or an optionally substituted (Ci-Ce)alkyl group, preferably hydrogen, and/or R 3 represents a hydrogen atom or a linear or branched (Ci-Ce)alkyl or (C 2 -C 6 )alkenyl group, such as ethenyl, optionally substituted with an aryl group, such as a phenyl group, which is optionally substituted, preferably with one or more (di)(Ci-C 4 )(alkyl)amino or hydroxyl groups.
  • Ri, R 2 and R 4 represent a hydrogen atom or a (Ci-C 4 )alkyl group, preferably hydrogen
  • the meta-hydroxyphenols according to the invention do not comprise two hydroxyl groups borne by two adjacent carbons.
  • the meta-hydroxyphenols of the invention may be natural or synthetic.
  • the salts of the meta- hydroxyphenols of the invention may be salts of acids or of bases.
  • the acids may be mineral or organic.
  • the acid is hydrochloric acid, which results in chlorides.
  • the bases may be mineral or organic.
  • the bases are alkaline hydroxides, such as sodium hydroxide, which results in sodium salts.
  • the composition comprises, as ingredient a), one or more synthetic meta-hydroxyphenol derivatives that do not exist in nature.
  • the natural meta-hydroxyphenols are derived from extracts of animals, bacteria, fungi, algae, plants and fruits, used in their entirety or partially.
  • the extracts are derived from fruits, including citrus fruits, from vegetables, from trees and from shrubs. Use may also be made of mixtures of these extracts, which are rich in meta-hydroxyphenols as defined above.
  • the non-thiol-based reducing agent(s) present in composition (C) according to the invention are chosen from para-hydroxyphenol derivatives with reducing properties.
  • para-hydroxyphenol denotes compounds which comprise at least one aromatic ring, preferably a benzene ring, comprising at least two hydroxyl (OH) groups borne by two adjacent carbon atoms which are in the para position relative to each other, and which also do not comprise any mercapto or disulfide groups.
  • non-thiol- based reducing agent(s) present in composition (C) are chosen from the para- hydroxyphenol derivatives of formula (IV), and also the organic or mineral acid or base salts thereof, and the solvates thereof such as hydrates:
  • R 1 to R 4 which may be identical or different, are as defined previously for formulae (II) and (III), and preferably represent a hydrogen atom or an optionally substituted (Ci-C4)alkyl group, preferably hydrogen.
  • the non-thiol-based agent(s) are chosen from catechol, gallic acid, para-hydroxyphenol or resveratrol, it being understood that, when the aromatic ring of the ortho-diphenols, meta-hydroxyphenols or para-hydroxyphenols bear more than two hydroxyl groups (for example three, four, etc.), the compounds should be understood according to the following rule:
  • the non-thiol-based reducing agent(s) represent from 1% to 10% by weight and preferably from 2% to 8% by weight relative to the total weight of composition (C) containing them.
  • the weight ratio between the amount of thiol-based reducing agent(s) and the amount of non-thiol-based reducing agent(s) is between 0.01 and 10, particularly between 0.1 and 5 inclusive, and more preferentially between 0.2 and 1 inclusive.
  • the pH of composition (C) is between 1 and 5 inclusive, preferably between 2.5 and 4. In one embodiment, the pH of composition (A) is between 1 and 5 inclusive, preferably between 2.5 and 4.
  • composition (C) comprising the non-thiol-based agent(s) is generally applied before and/or after composition (A) comprising the thiol-based agent(s), and preferably after composition (A).
  • the process according to the invention comprises step i) of applying composition (A), step o) of applying composition (C), step ii) of applying composition (B), and then iii) the heating step. This alternative is preferred.
  • the process of the invention preferably does not comprise a step of rinsing the keratin fibres between step i) and step o) before step ii) of applying composition (B).
  • composition(s) used according to the invention are non-dyeing, i.e. they do not comprise any direct dyeing or oxidation dyeing agents other than the non-thiol-based reducing agents or the compounds of formula (I) when they are coloured.
  • composition (C) when the compounds of formula (I) have a colouring function, for instance with a chromophore, the presence of composition (C) is preferable in the process for curl-relaxing.
  • the process comprises: - the application to the fibres of a composition (A) comprising said thiol-based agent(s) at a pH of between 1 and 5, and then
  • composition (C) comprising said non-thiol- based agent(s),
  • composition(s) used in the process according to the invention may also comprise one or more nonionic, anionic, cationic, or amphoteric or zwitterionic surfactants.
  • composition according to the present invention may optionally also comprise one or more surfactants.
  • the surfactant(s) that may be used in the composition according to the invention may be chosen from nonionic surfactants, cationic surfactants, anionic surfactants and amphoteric or zwitterionic surfactants, and mixtures thereof.
  • composition according to the present invention may thus comprise one or more nonionic surfactants.
  • nonionic surfactants that may be used are described, for example, in the Handbook of Surfactants by M.R. Porter, published by Blackie & Son (Glasgow and London), 1991, pages 116-178.
  • nonionic surfactants examples include the fo llo wing nonionic surfactants :
  • the oxyalkylene units are more particularly oxy ethylene or oxypropylene units, or a combination thereof, preferably oxyethylene units.
  • the number of moles of ethylene oxide and/or of propylene oxide preferably ranges from 1 to 250, more particularly from 2 to 100 and better still from 2 to 50; the number of moles of glycerol ranges in particular from 1 to 50 and better still from 1 to 10.
  • the nonionic surfactants according to the invention do not comprise any oxypropylene units.
  • glycerolated nonionic surfactants use is preferably made of monoglycerolated or polyglycerolated C8-C40 alcohols, comprising from 1 to 50 mol of glycerol and preferably from 1 to 10 mol of glycerol.
  • glycerolated alcohols it is more particularly preferred to use the C8/C10 alcohol containing 1 mol of glycerol, the C10/C12 alcohol containing 1 mol of glycerol and the C 12 alcohol containing 1.5 mol of glycerol.
  • nonionic surfactant(s) that may be used in the dye composition according to the invention are preferentially chosen from:
  • - oxyethylenated Cs to C40 alcohols comprising from 1 to 100 mol of ethylene oxide, preferably from 2 to 50 and more particularly from 2 to 40 mol of ethylene oxide and comprising one or two fatty chains;
  • - saturated or unsaturated oxyethylenated vegetable oils comprising from 1 to 100 and preferably from 2 to 50 mol of ethylene oxide;
  • - monoglycerolated or polyglycerolated Cs to C40 alcohols comprising from 1 to 50 mol of glycerol and preferably from 1 to 10 mol of glycerol;
  • composition according to the present invention may comprise one or more cationic surfactants.
  • cationic surfactant means a surfactant that is positively charged when it is contained in the compositions according to the invention. This surfactant may bear one or more positive permanent charges or may contain one or more cationizable functions in the compositions according to the invention.
  • the cationic surfactant(s) are preferably chosen from primary, secondary or tertiary fatty amines, which are optionally polyoxyalkylenated, or salts thereof, and quaternary ammonium salts, and mixtures thereof.
  • the fatty amines generally comprise at least one Cs to C30 hydrocarbon-based chain.
  • the groups R 2 8 to R31 which may be identical or different, represent a linear or branched aliphatic group containing from 1 to 30 carbon atoms, or an aromatic group such as aryl or alkylaryl, at least one of the groups R 2 8 to R31 denoting a group containing from 8 to 30 carbon atoms, preferably from 12 to 24 carbon atoms.
  • the aliphatic groups may comprise heteroatoms especially such as oxygen, nitrogen, sulfur and halogens.
  • the aliphatic groups are chosen, for example, from C1-C30 alkyl, C1-C30 alkoxy, polyoxy(C 2 -C6)alkylene, C1-C30 alkylamide, (Ci 2 -C 22 )alkylamido(C2- C 6 )alkyl, (Ci 2 -C 22 )alkyl acetate, and C1-C30 hydroxyalkyl groups,
  • X " is an anion chosen from the group of halides, phosphates, acetates, lactates, (Ci-C4)alkyl sulfates, and (Ci- C4)alkyl- or (Ci-C4)alkylarylsulfo nates.
  • the anion X " is preferably a halide (chloride, bromide or iodide) or an alkyl sulfate, more particularly methyl sulfate.
  • halide chloride, bromide or iodide
  • alkyl sulfate more particularly methyl sulfate.
  • methanesulfonate, phosphate, nitrate, tosylate an anion derived from an organic acid, such as acetate or lactate, or any other anion that is compatible with the ammonium bearing an ester function.
  • composition according to the present invention may comprise one or more anionic surfactants.
  • composition according to the present invention may comprise one or more amphoteric or zwitterionic surfactants.
  • amphoteric or zwitterionic surfactant(s), which are preferably non-silicone, which may be used in the composition according to the present invention may in particular be derivatives of optionally quaternized, secondary or tertiary aliphatic amines, in which derivatives the aliphatic group is a linear or branched chain comprising from 8 to 22 carbon atoms, said amine derivatives containing at least one anionic group, for instance a carboxylate, sulfonate, sulfate, phosphate or phosphonate group.
  • the surfactants that may be used in the process according to the invention are preferably nonionic or cationic.
  • the surfactant(s) represent from 0.1% to 20% by weight and better still from 1% to 10% by weight relative to the total weight of each composition containing them.
  • the composition(s) that may be used in the process according to the invention generally comprise water, which typically represents from 10%> to 90%> by weight, preferably from 10%> to 80%> by weight, preferably from 10%> to 70%> by weight, relative to the total weight of each composition.
  • compositions that may be used in the process according to the invention may also contain cosmetically acceptable organic solvents other than those contained in composition (B), more particularly including alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol and phenylethyl alcohol, or polyols or polyol ethers, for instance ethylene glycol monomethyl, monoethyl and monobutyl ethers, propylene glycol or ethers thereof, for instance propylene glycol monomethyl ether, butylene glycol, dipropylene glycol, and also diethylene glycol alkyl ethers, for instance diethylene glycol monoethyl ether or monobutyl ether.
  • alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol and phenylethyl alcohol
  • polyols or polyol ethers for instance ethylene glycol monomethyl, monoethyl and monobutyl ethers
  • propylene glycol or ethers thereof
  • the solvents may then represent from 0.5% to 20% by weight and preferably from 2% to 10% by weight relative to the total weight of each composition containing them.
  • compositions used according to the invention may also comprise one or more cosmetic adjuvants other than the compounds described previously.
  • they may comprise one or more standard additive(s) that are well known in the art, such as linear or cyclic, volatile or non- volatile silicones, cationic, nonionic, anionic or amphoteric polymers, peptides and derivatives thereof, protein hydrolysates, waxes, agents for preventing hair loss, vitamins and provitamins including panthenol, sunscreens, mineral or organic pigments, sequestrants, plasticizers, solubilizers, mineral or organic thickeners, antioxidants, nacreous agents, fragrances and preserving agents.
  • standard additive(s) such as linear or cyclic, volatile or non- volatile silicones, cationic, nonionic, anionic or amphoteric polymers, peptides and derivatives thereof, protein hydrolysates, waxes, agents for preventing hair loss, vitamins and provitamins including panthenol, sunscreens, mineral or organic pigments, sequestrants, plasticizers, solubilizers, mineral or organic thickeners, antioxidants,
  • the above additives may generally be present in an amount, for each of them, of between 0 and 20% by weight relative to the total weight of the composition containing them.
  • compositions according to the invention can choose the appropriate presentation form for the compositions according to the invention, and also the methods for preparing them, on the basis of his general knowledge, taking into account first the nature of the constituents used, in particular their solubility in the support, and secondly the application envisaged for the composition.
  • composition(s) according to the invention may be in the form of a suspension or a dispersion, in particular of oil-in- water by means of vesicles; an optionally thickened or even gelled oily solution; an oil-in-water, water-in-oil or multiple emulsion; a gel or a foam; an oily or emulsified gel; a dispersion of vesicles, in particular lipid vesicles; a two-phase or multiphase lotion; a spray.
  • compositions may have the appearance of a lotion, a cream, a salve, a soft paste, an ointment, a solid that has been cast or moulded and in particular as a stick or in a dish, or a compacted solid.
  • compositions used in the process according to the invention may thus be in any form that is compatible with application to keratin fibres, for example in the form of a wax, a paste, a more or less fluid or thick cream, a gel, a foam, a spray or a lotion.
  • compositions described previously are applied to wet or dry keratin fibres, sequentially or simultaneously.
  • compositions are usually left in place on the fibres for a time generally ranging from 1 minute to 1 hour and preferably from 5 minutes to 30 minutes for each composition.
  • the process according to the invention comprises a step of heat treatment of the fibres by means of a heating tool.
  • This heat treatment step is generally performed following the application of the composition(s) described above, optionally after removal thereof by rinsing.
  • the heating tool is chosen from a hairstyling hood, a straightening iron (or flat iron), a hairdryer and an infrared-ray dispenser, and more preferentially the heating tool is a straightening iron.
  • the iron is applied by successive separate strokes lasting a few seconds or by gradual movement or sliding along the locks.
  • the hair treatment step is generally performed at a temperature ranging from 30 to 250°C, preferably from 60 to 230°C and more preferentially from 100 to 150°C.
  • the process for treating keratin fibres comprises, as heat treatment, a step of straightening/uncurling the keratin fibres by means of a heating tool chosen from irons and a steam iron, i.e. "irons" which comprise a device that emits steam and that applies this steam before, during or after the straightening/uncurling.
  • a heating tool chosen from irons and a steam iron, i.e. "irons” which comprise a device that emits steam and that applies this steam before, during or after the straightening/uncurling.
  • iron means a device for heating keratin fibres by placing said fibres and the heating device in contact.
  • the end of the iron which comes into contact with the keratin fibres generally has two flat surfaces. These two surfaces may be made of metal or of ceramic. In particular, these two surfaces may be smooth or crimped or curved.
  • the iron or the steam iron is at a temperature of between 65°C and 250°C, particularly between 80°C and 230°C, more particularly greater than or equal to 100°C and preferentially between 100°C and 190°C.
  • the heat treatment step of the process for treating keratin fibres is performed at a temperature ranging from 150°C to 230°C, preferably ranging from 160°C to 230°C, preferentially ranging from 160°C to 210°C, especially ranging from 180°C to 200°C.
  • irons that may be used in the straightening process according to the invention, mention may be made of any type of flat steam iron, and in particular, in a non-limiting manner, those described in patents US 5 957 140 and US 5 046 516.
  • the steam iron may be applied by successive separate strokes lasting a few seconds or by gradual movement or sliding along the locks of keratin fibres, especially of hair.
  • the steam iron is applied in the process according to the invention by a continuous movement from the root to the end of the hair, in one or more passes, in particular in two to twenty passes.
  • the duration of each pass of the steam iron may range from 2 seconds to 1 minute.
  • steam is applied to the keratin fibres, especially the hair, at a flow rate of less than 5 g/min, especially of between 1 and 4 g/min.
  • Steam may be applied using any device known per se for generating the amount of steam of use in the process of the invention.
  • this machine is portable, i.e. the tank for generating steam is in contact with the part of the device comprising the steam-dispensing orifices.
  • the steam application step may be performed before, during or after the heating step, and preferably before.
  • the step of straightening/relaxing the keratin fibres is performed for a time that may range from 2 seconds to 30 minutes, preferentially from 2 seconds to 20 minutes, better still from 2 seconds to 10 minutes, better still from 2 seconds to 5 minutes and even better still from 2 seconds to 2 minutes.
  • step ii) is performed with a steampod steam straightening device.
  • the process according to the invention may also comprise an additional step of drying the keratin fibres, after the application steps i), optionally o) and ii), and before the heat treatment step iii).
  • the drying step may be performed using a hairdryer or a drying hood or by drying in the open air.
  • the drying step is advantageously performed at a temperature ranging from 20 to 70°C.
  • the keratin fibres may be optionally rinsed with water or washed with a shampoo.
  • the keratin fibres are subsequently optionally dried using a hairdryer or a drying hood or in the open air.
  • the process according to the invention is performed on natural keratin fibres, especially natural hair.
  • the process according to the invention is performed on keratin fibres, especially damaged hair.
  • damaged hair means dry or coarse or brittle or split or limp hair.
  • the process of the invention is particularly performed on sensitized human keratin fibres, especially hair, such as bleached, relaxed or permanent-waved fibres.
  • the process according to the invention may be performed on keratin fibres, especially hair, which is wet or dry. Preferentially, the process is performed on natural keratin fibres.
  • composition(s) A and/or B applied may be left on for a period ranging from 1 to 60 minutes, preferably ranging from 2 to 50 minutes, preferentially ranging from 5 to 45 minutes.
  • the leave-on period may take place at a temperature ranging from 15°C to 45°C, preferably at room temperature (25°C).
  • the cosmetic composition which contains the thiol-based reducing agents, as described previously, is advantageously applied to the keratin fibres in an amount ranging from 0.1 to 10 grams and preferably from 0.2 to 5 grams of composition per gram of keratin fibres.
  • the cosmetic composition which contains the non-thiol-based reducing agents, as described previously, is advantageously applied to the keratin fibres in an amount ranging from 0.1 to 10 grams and preferably from 0.2 to 5 grams of composition per gram of keratin fibres.
  • said fibres may be wrung out to remove the excess composition or washed with water or with a shampoo.
  • the treatment process according to the invention may be performed before, during and/or after an additional process of cosmetic treatment of the keratin fibres, such as a process for temporary curl relaxation (relaxing of curls with curlers, a crimping iron or a straightening iron) or a process for long-lasting curl relaxation (permanent-waving or uncurling) of the keratin fibres.
  • an additional process of cosmetic treatment of the keratin fibres such as a process for temporary curl relaxation (relaxing of curls with curlers, a crimping iron or a straightening iron) or a process for long-lasting curl relaxation (permanent-waving or uncurling) of the keratin fibres.
  • the process according to the invention may also comprise an additional step of partially predrying the hair fibres before the step of increasing the temperature, so as to prevent the evolution of large amounts of steam, which might burn the hairstylist's hands and the subject's scalp.
  • This predrying step may be performed, for example, by means of a dryer or of a drying hood or else by drying in the open air.
  • the keratin fibres may optionally be washed with a shampoo, followed by rinsing with water, before being dried or left to dry.
  • the process according to the invention may be repeated so as to increase the effects, until the desired level of straightening is obtained.
  • this constitutes an advantage of the present invention from the very first implementation of the process according to the invention, including implementation without placing the hair under tension, a substantial reduction in the volume of the head of hair is observed. When the hair is curly, relaxation of the curls and/or better curl definition are also observed.
  • the process is repeated several times, either consecutively or after a delay ranging from a few hours to a few days.
  • a subject of the present invention is also an acidic composition, preferably with a pH of between 1 and 5 inclusive and containing one or more thiol-based reducing agents as defined previously, and one or more disulfide compounds of formula (I):
  • a subject of the present invention is also a kit that is suitable for performing the process of the invention.
  • This kit comprises at least two compartments:
  • composition (A) which comprises one or more thiol-based reducing agents, as defined above, at a pH of between 1 and 5 inclusive, preferentially between 2.5 and 4,
  • composition (B) which comprises one or more compounds of formula (I) as defined above, and
  • a third compartment comprising a composition (C) which comprises one or more non-thiol-based reducing agents, as defined above.
  • compositions of this kit are packaged in separate compartments, which may be optionally accompanied by suitable identical or different application means, such as fine brushes, coarse brushes or sponges.
  • kit may also be equipped with means for dispensing the desired mixture on the hair, for instance the device described in patent FR 2 586 913.
  • Thio lactic acid is tested comparatively in solution at 1% or at 8% by weight in water at pH 3.5.
  • the locks of keratin fibres were combed, and then were subjected to 10 successive blow drying passes, at position 2 (80°C) of the hairdryer, with a medium- diameter round brush. Each of the locks was then separated into two. Each part was subjected to 10 passes with the straightening iron using a comb on each half, then 2/3 passes over all of it at 230°C.
  • Control 2 The protocol used for the "Control 2" consists in applying a thiol-based reducing agent at 8% by weight for 30 minutes, rinsing, blow-drying and treating with an iron at a temperature of 230°C.
  • the protocol named "Gl” consists of an application of 8% thiol-based reducing agent for 30 minutes, the application of compound 15 for 20 minutes, blow-drying and treating with an iron at a temperature of 230°C.
  • the protocol named "G2" consists of an application of 1% thiol-based reducing agent for 30 minutes, the application of 5% para-hydroxyphenol for 10 minutes, the application of 10% compound 15 for 20 minutes, blow-drying and treating with an iron at a temperature of 230°C.
  • the protocol named "G3" consists of an application of 1% thiol-based reducing agent for 30 minutes, the application of 10% compound 15 for 20 minutes, the application of 5% para-hydroxyphenol for 10 minutes, blow-drying and treating with an iron at a temperature of 230°C.

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Abstract

La présente invention concerne un procédé de défrisage et/ou de lissage de fibres kératiniques, telles que les cheveux, qui comprend l'application sur les fibres d'une ou plusieurs compositions comprenant des agents réducteurs, d'une ou plusieurs compositions comprenant des composés disulfures cationiques et une étape de traitement thermique des fibres au moyen d'un outil de chauffage. L'invention concerne également l'utilisation de la ou des compositions comprenant des agents réducteurs et de la ou des compositions comprenant des composés disulfures cationiques dans un procédé de défrisage et/ou de lissage de fibres kératiniques. Enfin, l'invention concerne un dispositif à compartiments multiples ou "kit" qui convient à la mise en œuvre d'un tel procédé.
PCT/EP2017/084298 2016-12-22 2017-12-22 Procédé de défrisage et/ou de lissage de fibres kératiniques faisant appel à des agents réducteurs et à des composés disulfures cationiques, et kit de lissage WO2018115394A1 (fr)

Applications Claiming Priority (2)

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FR1663187 2016-12-22
FR1663187A FR3060989B1 (fr) 2016-12-22 2016-12-22 Procede de detente de boucles et/ou de lissage des fibres keratiniques, mettant en oeuvre des agents reducteurs et des composes disulfure cationiques, et kit de lissage

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2586913A1 (fr) 1985-09-10 1987-03-13 Oreal Procede pour former in situ une composition constituee de deux parties conditionnees separement et ensemble distributeur pour la mise en oeuvre de ce procede
EP0261387A1 (fr) * 1986-09-20 1988-03-30 Wella Aktiengesellschaft Composition et procédé d'ondulation permanente des cheveux
US5046516A (en) 1988-10-31 1991-09-10 George Barradas Hair curling iron
WO1993016991A1 (fr) * 1992-02-28 1993-09-02 Consejo Superior Investigaciones Científicas Tensioactifs cationiques contenant dans leurs molecules un groupe bisulfure, procede de production
US5957140A (en) 1998-11-19 1999-09-28 Mcgee; Robert J. Hair styling iron for straightening and curling
WO2006126729A2 (fr) * 2005-05-27 2006-11-30 Showa Denko K.K. Produit de permanente pour cheveux contenant un compose mercapto heterocyclique
WO2007135298A1 (fr) * 2006-05-24 2007-11-29 L'oreal Procede de defrisage des fibres keratiniques avec un moyen de chauffage et un compose aromatique
EP2196191A1 (fr) * 2008-12-11 2010-06-16 L'oreal Composition cosmetique comprenant un compose heterocyclique disulfure et un agent reducteur et procede pour la deformation permanente des fibres keratiniques

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2586913A1 (fr) 1985-09-10 1987-03-13 Oreal Procede pour former in situ une composition constituee de deux parties conditionnees separement et ensemble distributeur pour la mise en oeuvre de ce procede
EP0261387A1 (fr) * 1986-09-20 1988-03-30 Wella Aktiengesellschaft Composition et procédé d'ondulation permanente des cheveux
US5046516A (en) 1988-10-31 1991-09-10 George Barradas Hair curling iron
WO1993016991A1 (fr) * 1992-02-28 1993-09-02 Consejo Superior Investigaciones Científicas Tensioactifs cationiques contenant dans leurs molecules un groupe bisulfure, procede de production
US5957140A (en) 1998-11-19 1999-09-28 Mcgee; Robert J. Hair styling iron for straightening and curling
WO2006126729A2 (fr) * 2005-05-27 2006-11-30 Showa Denko K.K. Produit de permanente pour cheveux contenant un compose mercapto heterocyclique
WO2007135298A1 (fr) * 2006-05-24 2007-11-29 L'oreal Procede de defrisage des fibres keratiniques avec un moyen de chauffage et un compose aromatique
EP2196191A1 (fr) * 2008-12-11 2010-06-16 L'oreal Composition cosmetique comprenant un compose heterocyclique disulfure et un agent reducteur et procede pour la deformation permanente des fibres keratiniques

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
J. MARCH: "Advanced Organic Chemistry, Reactions, Mechanisms and Structure", 1992
M.R. PORTER: "Handbook of Surfactants", 1991, BLACKIE & SON, pages: 116 - 178
PINAZO A ET AL: "SYNTHESIS AND PROPERTIES OF CATIONIC SURFACTANTS CONTAINING A DISULFIDE BOND", JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY (JAOCS), SPRINGER, DE, vol. 70, no. 1, 1 January 1993 (1993-01-01), pages 37 - 42, XP000338539, ISSN: 0003-021X, DOI: 10.1007/BF02545364 *
SANTANU BHATTACHARYA ET AL: "Synthesis and Characterization of Novel Cationic Lipid and Cholesterol-Coated Gold Nanoparticles and Their Interactions with Dipalmitoylphosphatidylcholine Membranes", LANGMUIR, vol. 19, no. 10, 1 May 2003 (2003-05-01), pages 4439 - 4447, XP055182496, ISSN: 0743-7463, DOI: 10.1021/la0269513 *

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