[go: up one dir, main page]

WO2017018498A1 - Composition, processus, procédé et utilisation destinés à des fibres de kératine - Google Patents

Composition, processus, procédé et utilisation destinés à des fibres de kératine Download PDF

Info

Publication number
WO2017018498A1
WO2017018498A1 PCT/JP2016/072243 JP2016072243W WO2017018498A1 WO 2017018498 A1 WO2017018498 A1 WO 2017018498A1 JP 2016072243 W JP2016072243 W JP 2016072243W WO 2017018498 A1 WO2017018498 A1 WO 2017018498A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
radical
keratin fibers
weight
polyol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2016/072243
Other languages
English (en)
Inventor
Qinghua Li
Tomotaka Michitsuji
Hayato Nishimura
Daisuke Ishii
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by LOreal SA filed Critical LOreal SA
Publication of WO2017018498A1 publication Critical patent/WO2017018498A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • 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 composition, in particular a cosmetic composition, and a reshaping process, in particular waving, as well as a method and a use, for keratin fibers such as hair.
  • the new shape imposed on the keratin fibers by chemical treatment as described above is relatively long-lasting and notably withstands the action of washing with water or shampoo, in contrast to the simple conventional techniques of temporary styling by using foams, styling gels, or lacquers.
  • compositions and processes for the above chemical treatment have been proposed. Generally, they offer good performance on the day of treatment.
  • An objective of the present invention is to provide a composition, preferably a cosmetic composition, for keratin fibers, such as hair, which can be used to deform or reshape the keratin fibers, and can provide the keratin fibers with sufficient reshaping efficiency such as strong wave intensity, distinct wave deepness and good regularity of curl, as well as less damage to the keratin fibers which results in excellent hair conditioning effects such as good elasticity and suppleness of the keratin fibers.
  • the above objective of the present invention can be achieved by a composition, in particular a cosmetic composition, for keratin fibers, such as hair, comprising:
  • the amount of the polyol in the composition is less than 1.0% by weight relative to the total weight of the composition.
  • the (b) polyol may be selected from glycols.
  • the (b) polyol may be selected from the group consisting of butylene glycol, pentylene glycol, hexylene glycol, and mixtures thereof.
  • the amount of the (b) polyol(s) in the composition may be from 0.001 to less than 1.0% by weight, preferably from 0.01 to less than 0.5% by weight, and more preferably from 0.1 to 0.3% by weight, relative to the total weight of the composition.
  • the (a) reducing agent may be selected from the group consisting of thioglycolic acid, thiolactic acid, cysteine, N-acetylcysteine, cysteamine, lactonethiol compounds such as butyrolactonethiol, glyceryl monothioglycolate, sulfite or bisulfite compounds, thioglycerine, their derivatives, and their salts.
  • the amount of the (a) reducing agent(s) in the composition may be from 0.01 to 25% by weight, preferably from 0.1 to 20% by weight, and more preferably from 1.0 to 15% by weight, relative to the total weight of the composition.
  • composition according to the present invention may further comprise (c) at least one alkaline agent.
  • composition according to the present invention may have a pH of 9.0 or less, preferably 8.5 or less, and more preferably 8.0 or less.
  • composition according to the present invention may further comprise (d) at least one surfactant.
  • the composition according to the present invention may be free of dicarboxylic acid, preferably ⁇ , ⁇ -dicarboxylic acid with 5 to 10 carbon atoms, and more preferably adipic acid.
  • the composition according to the present invention is preferably intended for reshaping, in particular permanent waving, of keratin fibers, preferably the hair.
  • the composition according to the present invention can be used to deform or reshape keratin fibers, preferably the hair, and can provide the keratin fibers with sufficient reshaping efficiency such as strong wave intensity, distinct wave deepness and good regularity of curl, as well as excellent hair conditioning effects due to less damage to the keratin fibers, such as good elasticity and suppleness of the keratin fibers.
  • the present invention also relates to a reshaping process, in particular permanent waving, for keratin fibers, preferably the hair, comprising the steps of:
  • an oxidizing composition comprising at least one oxidizing agent
  • composition comprises
  • the amount of the polyol in the composition is less than 1.0% by weight relative to the total weight of the composition.
  • the present invention also relates to a method for enhancing reshaping efficiency of keratin fibers with less damage to the keratin fibers provided by a reducing composition comprising at least one reducing agent in combination with an oxidizing composition comprising at least one oxidizing agent, characterized by adding at least one polyol with 4 or more carbon atoms to the reducing composition in an amount of less than 1.0% by weight relative to the total weight of the reducing composition.
  • the present invention also relates to a use of at least one polyol with 4 or more carbon atoms in a reducing composition comprising at least one reducing agent wherein the amount of the polyol in the reducing composition is less than 1.0% by weight relative to the total weight of the reducing composition, for enhancing reshaping efficiency of keratin fibers with less damage to the keratin fibers provided by the reducing composition in combination with an oxidizing composition comprising at least one oxidizing agent.
  • the process, method and use according to the present invention can be used to deform or reshape keratin fibers, preferably hair, and can provide the keratin fibers with sufficient reshaping efficiency such as strong wave intensity, distinct wave deepness and good regularity of curl, as well as excellent hair conditioning effects due to less damage to the keratin fibers, such as good elasticity and suppleness of the keratin fibers.
  • one aspect of the present invention is a composition, in particular a cosmetic composition, for keratin fibers, such as hair, comprising:
  • the amount of the polyol in the composition is less than 1.0% by weight relative to the total weight of the composition.
  • Another aspect of the present invention is a reshaping process, in particular permanent waving, for keratin fibers, preferably the hair, comprising the steps of:
  • an oxidizing composition comprising at least one oxidizing agent
  • composition comprises
  • the amount of the polyol in the composition is less than 1.0% by weight relative to the total weight of the composition.
  • Another aspect of the present invention is a method for enhancing reshaping efficiency of keratin fibers with less damage to the keratin fibers provided by a reducing composition comprising at least one reducing agent in combination with an oxidizing composition comprising at least one oxidizing agent, characterized by adding at least one polyol with 4 or more carbon atoms to the reducing composition in an amount of less than 1.0% by weight relative to the total weight of the reducing composition.
  • Another aspect of the present invention is a use of at least one polyol with 4 or more carbon atoms in a reducing composition comprising at least one reducing agent wherein the amount of the polyol in the reducing composition is less than 1.0% by weight relative to the total weight of the reducing composition, for enhancing reshaping efficiency of keratin fibers with less damage to the keratin fibers provided by the reducing composition in a combination of an oxidizing composition comprising at least one oxidizing agent.
  • composition (Reducing Agent)
  • the composition according to the present invention comprises at least one (a) reducing agent. Two or more reducing agents may be used in combination. Thus, a single type of reducing agent or a combination of different types of reducing agents may be used.
  • the (a) reducing agent(s) may be present in the composition according to the present invention, in an amount of, for example, from 0.01 to 25% by weight, preferably from 0.1 to 20% by weight, and more preferably from 1.0 to 15% by weight, relative to the total weight of the composition.
  • the (a) reducing agent may be selected from thiol reducing agents and non-thiol reducing agents.
  • thiol reducing agent here means a reducing agent with at least one thiol group.
  • the thiol reducing agent may preferably be chosen from the group consisting of thioglycolic acid and derivatives thereof, in particular esters thereof such as glycerol or glycol
  • monothioglycolate thiolactic acid and derivatives thereof, in particular esters thereof such as glycerol monothiolactate; 3-mercaptopropionic acid and derivatives thereof, in particular esters thereof such as glycerol 3-mercaptopropionate and ethyleneglycol
  • cysteamine and derivatives thereof in particular Q-Q acyl derivatives thereof such as N-acetylcysteamine and N-propionylcysteamine; mono-thioglycerol and derivatives thereof, in particular esters; cysteine and derivatives thereof, in particular esters such as N-acetylcysteine, N-alkanoylcysteine and cysteine alkyl esters; thioglycerine and derivatives thereof, in particular s-alkyl derivatives, and salts thereof.
  • Q-Q acyl derivatives thereof such as N-acetylcysteamine and N-propionylcysteamine
  • mono-thioglycerol and derivatives thereof in particular esters
  • cysteine and derivatives thereof in particular esters such as N-acetylcysteine, N-alkanoylcysteine and cysteine alkyl esters
  • thioglycerine and derivatives thereof in particular s-alkyl derivative
  • salts mention may be made of, for example, ammonium salts; primary-, secondary- or tertiary-amine salts; alkaline metal salts; and alkaline earth metal salts.
  • primary-, secondary- or tertiary-amine for example, monoethanolamine, di-isopropanolamine or triethanolamine, respectively, may be mentioned.
  • mercapto carboxylic acid or amine As the thiol reducing agent, it is preferable to use mercapto carboxylic acid or amine.
  • the mercapto carboxylic acid or amine here means a compound with at least one mercapto group and at least one carboxyl group or at least one amino group. It is preferable that the mercapto carboxylic acid or amine have one mercapto group and one carboxyl group or one amino group.
  • the mercapto carboxylic acid or amine here does not encompass a compound with both carboxyl and amino groups such as cysteine and homocysteine.
  • the mercapto carboxylic acid As examples of the mercapto carboxylic acid, mention may be made of thioglycolic acid, thiolactic acid, 3-mercapto propionic acid, thiotartaric acid, mercapto succinic acid (thiomalic acid), and dimercapto adipic acid. It is preferable that the mercapto carboxylic acid be selected from the group consisting of thioglycolic acid, thiolactic acid, and
  • the mercapto carboxylic acid may be in the form of a derivative thereof.
  • the mercapto carboxylic acid derivative here means a compound in which the OH moiety of the mercapto carboxylic acid has been replaced with another group such as alkoxy group and amino group.
  • the mercaptocarboxylic acid derivative can be prepared by the reaction between the mercapto carboxylic acid and, for example, alcohols or amines.
  • mercapto carboxylic acid derivatives examples include mercapto caboxylates such as methylthioglycolate, ethylthioglycolate, glycolmonothioglycolate, 1 ,2-propyleneglycolmonothioglycolate, glycerolmonothioglycolate, glycolmonothiolactate, glycerolmonothiolactate, and glycerolmono-3-mercaptopropionate; and mercaptocarboxylic acid amides such as thioglycolamide, N-hydroxyethylthioglycolamide, 3 -mercaptopropionamide, and N-hydroxyethyl-3 -mercaptopropionamide.
  • mercapto caboxylates such as methylthioglycolate, ethylthioglycolate, glycolmonothioglycolate, 1 ,2-propyleneglycolmonothioglycolate
  • cysteamine As examples of the mercapto amine, mention may be made of cysteamine and cysteamine derivatives. As examples of the cysteamine derivatives, mention may be made of
  • N-acylcysteamines As the acyl group of the N-acylcysteamines, mention may be made of an alkanoyl group such as acetyl, octanoyl, decanoyl, lauroyl, myristoyl, palmitoyl, stearoyl, isostearoyl, and the like. As the cysteamine derivative, N-acetylcysteamine is preferable.
  • mercapto carboxylic acid or amine in combination with cysteine or a derivative thereof as mentioned above.
  • ⁇ , ⁇ -dialkylmercapto 4-butyramides such as those described in European Patent Application No. 0 368 763; aminomercaptoalkyl amides such as those described in European Patent Application No. 0 432 000 and alkylaminomercaptoalkylamides such as those described in European Patent Application No. 0 514 282; (2/3) hydroxy-2 propyl thioglycolate; and the hydroxy-2 methyl- 1 ethyl thioglycolate-based mixture (67/33) described in French Patent Application No. 2 679 448.
  • the thiol reducing agent be selected from the group consisting of thioglycolic acid, thiolactic acid, cysteine, N-acetylcysteine, cysteamine, lactonethiol compound such as butyrolactonethiol, glyceryl monothioglycolate, sulfite or bisulfite compounds, thioglycerine, their derivatives, and their salts such as ethanolamine thioglycolate, ammonium thioglycolate and cysteamine HC1.
  • non-thiol reducing agent here means a reducing agent with no thiol group.
  • the non-thiol reducing agent may preferably be chosen from the group consisting of sulfites, bisulfites, sulfinates, phosphines, sugars, reductones and hydrides. More preferably, the non-thiol reducing agent may be selected from ammonium sulfites and bisulfites as well as metal sulfites and bisulfites, more preferably alkali metal or alkali earth metal sulfites and bisulfites, and more preferably sodium sulfites and bisulfites.
  • the sulfinates mention may be made of sulfmic acid salts, and benzenesulfmic acid salts such as sodium salts thereof.
  • the sulfinic acid derivatives as described in FR-A-2814948 can also be used.
  • a preferred sulfinate compound is 2-hydroxy-2-sulfinatoacetic acid, disodium salt.
  • the phosphines mention may be made of monophosphine and diphosphines as described in FR-A-2870119. According to one particular embodiment of the present invention, the phosphine(s) can be chosen from the compounds of formula (I) below:
  • L is a linker that represents a covalent bond or a divalent hydrocarbon-based radical optionally comprising one or more hetero atoms chosen from an oxygen atom, a sulfur atom, a nitrogen atom and a silicon atom;
  • n is an integer equal to 0 or 1 ;
  • q is an integer equal to 1 or 2;
  • p is an integer equal to 0 or 1 ;
  • R J1 , R J and R which may be identical or different, represent:
  • a monovalent hydrocarbon-based radical optionally comprising one or more hetero atoms chosen from a sulfur atom, an oxygen atom, a nitrogen atom, a phosphorus atom and a silicon atom, optionally substituted with one or more radicals chosen from:
  • an aromatic or heteroaromatic ring which is unsubstituted or substituted with one or more radicals chosen from a halogen atom, a hydroxyl radical, an alkoxy radical and a mono- or di(alkyl)amino radical,
  • a radical that increases the solubility of the phosphine in water such as sulfonate, sulfinate, phosphonate or carboxylate radicals,
  • the substituents are chosen from halo, hydroxyl, alkyl, haloalkyl, alkoxy, amino, mono- or dialkylamino, mono- or
  • the radical p-methoxyphenyl is a substituted aryl radical.
  • the radicals R , R and R do not simultaneously represent a hydrogen atom.
  • R , R and R denotes, as a hydrocarbon-based radical, an optionally substituted alkyl radical.
  • R , R and R are chosen from a hydrogen atom; an alkyl radical; a cycloalkyl radical optionally substituted with one or more alkyl radicals; an alkoxy radical; an alkoxyalkyl radical; a haloalkyl radical; a cyanoalkyl radical; a hydroxyalkyl radical; a carboxyalkyl radical; a halogen atom; a hydroxyl radical; a carboxyl radical; an alkenyl radical; a mono- or dialkylamino radical; an
  • N-aryl-N-alkylaminoalkyl radical an aryl radical optionally substituted with one or more radicals chosen from an alkyl radical, an alkoxy radical, a mono- or dialkylamino radical, a mono- or dialkylaminoalkyl radical, a haloalkyl radical, a hydroxyl radical, a carboxyl radical, a halogen atom, and an aryl radical substituted with a mono- or dialkylaminoalkyl radical; an arylalkyl radical; an arylalkyloxy radical; a pyrrolidino radical; a furyl radical; a morpholino radical; a thienyl radical; a pyridyl radical; a trialkylsilyl radical; and an alkyl radical substituted with a pyrrolidino radical, a furyl radical, a morpholino radical or a thienyl radical.
  • R , R and R may be chosen from a hydrogen atom; a methyl radical; an ethyl radical; a propyl radical; an isopropyl radical; an n-butyl radical; an isobutyl radical; a tert-butyl radical; an octyl radical; a cyclohexyl radical; a cyclopentyl radical; a methoxy radical; an ethoxy radical; a methoxypropyl radical; a chloroethyl radical; a cyanoethyl radical; a hydroxymethyl radical; a hydroxypropyl radical; a carboxyethyl radical; a chlorine atom; a hydroxyl radical; a carboxyl radical; a trifluoromethyl radical; a chloromethyl radical; an allyl radical; a vinyl radical; a dimethylamino radical; a diethylamino radical; a
  • di(isopropyl)amino radical a phenyl radical; an o-tolyl radical; an m-tolyl radical; a p-tolyl radical; a dimethylphenyl radical; a trimethylphenyl radical; an o-methoxyphenyl radical; an m-methoxyphenyl radical; a p-methoxyphenyl radical; a dimethoxyphenyl radical; a trimethoxyphenyl radical; an o-(dimethylamino)phenyl radical; an m-(dimethylamino)phenyl radical; a p-(dimethylamino)phenyl radical; a di(tert-butyl)phenyl radical; a
  • tri(tert-butyl)phenyl radical a trifluoromethylphenyl radical; a bis(trifluoromethyl)phenyl radical; an o-fluorophenyl radical; an m-fiuorophenyl radical; a p-fluorophenyl radical; an o-chlorophenyl radical; an m-chlorophenyl radical; a p-chlorophenyl radical; an
  • o-hydroxyphenyl radical an m-hydroxyphenyl radical; a p-hydroxyphenyl radical; a
  • 2-(4-diethylaminomethyl-phenyl)phenyl radical ; a 5-methyl-2-isopropylcyclohexyl radical; an N-methyl-N-phenylaminomethyl radical; and a carboxyphenyl radical.
  • the phosphines that are useful in the context of the present invention may be optionally salified with strong mineral acids, for instance HCl, HBr, H 2 S0 4 or HBF 4 or organic acids, for instance acetic acid, lactic acid, tartaric acid, citric acid or succinic acid.
  • the phosphine(s) that is (are) useful in the context of the present invention is (are) chosen from monophosphines.
  • q is then preferably equal to 1.
  • monophosphines examples include tri(hydroxymethyl)phosphine; tri(hydroxypropyl)phosphine; bis(hydroxymethyl)(phenyl)phosphine; allyldiphenylphosphine; benzyldiphenylphosphine; bis(3,4,5-trimethoxyphenyl)chlorophosphine;
  • diallylphenylphosphine dibenzylphosphine; dibutylphenylphosphine; dibutylphosphine;
  • dicyclohexylchlorophosphine dicyclohexylphenylphosphine; dicyclohexylphosphine;
  • diethylchlorophosphine diethylphenylphosphine; diethylphosphine; diisobutylphosphine; diisopropylchlorophosphine; diisopropylphosphine; dimethyl(phenyl)phosphine;
  • dimethyl(trimethylsilyl)phosphine dimethylchlorophosphine; diphenyl(o-tolyl)phosphine; diphenyl(p-tolyl)phosphine; diphenyl(trimethylsilyl)phosphine; diphenylchlorophosphine; diphenylphosphine; diphenylpropylphosphine; diphenylvinylphosphine;
  • di-tert-butylchlorophosphine di-tert-butylhydroxyphosphine; di-tert-butylmethylphosphine; di-tert-butylphenylphosphine; di-tert-butylphosphine; divinylphenylphosphine; ethyl-dichlorophosphine; ethyldiphenylphosphine; isopropyl-dichlorophosphine; methoxydiethoxyphosphine; methyl-dichlorophosphine; methyldiphenylphosphine;
  • tert-butyldiethylphosphine tert-butyldiphenylphosphine; tert-butylphosphine;
  • the monophosphines are chosen from trihydroxymethylphosphine
  • the phosphine(s) that is (are) useful in the context of the present invention is (are) diphosphines.
  • q is then preferably equal to 2.
  • p is equal to 0 and the linker L is a covalent bond or a divalent radical chosen from a binaphthylene radical; a methylene radical; an ethylene radical; a propylene radical; a butylene radical; a pentylene radical; a hexylene radical; a phenylene radical; a
  • meta-dimethylenebenzene radical an N-methyl-N'-methylhydrazo radical; a vinylene radical; and a diethyleneoxy radical.
  • diphosphines that are useful in the context of the present invention, mention may be made of 2,2'-bis(dicyclohexyiphosphino)- 1 , 1 '-binaphthyl;
  • the phosphine(s) that is (are) useful in the context of the present invention is (are) soluble in a cosmetically acceptable medium.
  • the phosphine(s) that is (are) useful in the context of the present invention is (are) water-soluble.
  • water-soluble means any phosphine whose solubility in water is greater than 0.01%, preferably greater than 1%, and even preferably greater than 2 or 5% by weight at 20°C and at atmospheric pressure (760 mm Hg, i.e.
  • the phosphine is trihydroxymethylphosphine.
  • sugars mention may be made of ribose, glucose, maltose, galactose, lactose, and xylose.
  • reductones mention may be made of ascorbic acid and erythorbic acid.
  • boron hydrides such as sodium borohydride, lithium hydride, and phosphorous hydride.
  • Precursors of hydrides and especially of boron hydrides such as diborane, tetraborane, pentaborane, decaborane and dodecaborane can be used.
  • Preferred non-thiol-based reducing agents are chosen from sulfites, bisulfites and phosphines.
  • non-thiol reducing agent(s) it may be preferable to use non-thiol reducing agent(s) because the malodor derived from sulfur atom(s) can be reduced or avoided.
  • composition according to the present invention also comprises at least one (b) polyol with 4 or more carbon atoms.
  • Two or more polyols may be used in combination.
  • a single type of polyol or a combination of different types of polyols may be used.
  • polyol here means an alcohol having two or more hydroxy groups, and does not encompass a saccharide or a derivative thereof.
  • the derivative of a saccharide includes a sugar alcohol which is obtained by reducing one or more carbonyl groups of a saccharide, as well as a saccharide or a sugar alcohol in which the hydrogen atom or atoms in one or more hydroxy groups thereof has or have been replaced with at least one substituent such as an alkyl group, a hydroxyalkyl group, an alkoxy group, an acyl group or a carbonyl group.
  • the (b) polyol can promote the penetration of the (a) reducing agent(s) into the keratin fibers, and can reduce or cancel hydrophobic interactions that are non-reactive bonds in the keratin fibers. Due to the use of the (b) polyol with the (a) reducing agent(s), cancellation of the internal bonds in the keratin fibers can be performed even with a small amount of the (a) reducing agent(s). Therefore, the deformation of keratin fibers is possible with reduced damage due to the use of a small amount of the (a) reducing agent(s).
  • the (b) polyol may be a C 4 -C 12 polyol, preferably a C 4 -C 9 polyol, and more preferably a C 4 -C 6 polyol, comprising at least 2 hydroxy groups, and preferably 2 to 5 hydroxy groups.
  • the (b) polyol with 4 or more carbon atoms may be a natural or synthetic polyol.
  • the polyol may have a linear, branched or cyclic molecular structure.
  • the (b) polyol may be selected from glycerins and glycols.
  • the (b) polyol may be selected from the group consisting of diglycerin, polyglycerin, diethyleneglycol, dipropyleneglycol, polyethyleneglycol (5 to 50 ethyleneoxide groups), polypropyleneglycol(5 to 50
  • propyleneoxide groups butyleneglycol, pentyleneglycol, hexyleneglycol, and a combination thereof.
  • the (b) polyol be selected from glycols, preferably a C 4 -C 12 glycol, more preferably a C 4 -C 9 glycol, and even more preferably a C 4 -C 6 glycol, comprising at least 2 hydroxy groups.
  • the (b) polyol be selected from the group consisting of butylene glycol, pentylene glycol, hexylene glycol, and mixtures thereof.
  • the amount of the (b) polyol(s) in the composition may be from 0.001 to less than 1.0% by weight, preferably from 0.01 to 0.5% by weight, and more preferably from 0.1 to 0.3% by weight, relative to the total weight of the composition.
  • the use of the (b) polyol in an amount of 1.0% by weight or more, preferably 1.5% by weight or more, and more preferably 2.0% by weight or more, relative to the total weight of the composition is not preferable, because the reshaping efficiency of the keratin fibers can be deteriorated.
  • the composition according to the present invention may comprise (c) at least one alkaline agent. Two or more (c) alkaline agents may be used in combination. Thus, a single type of alkaline agent or a combination of different types of alkaline agents may be used.
  • the (c) alkaline agent may be an inorganic alkaline agent. It is preferable that the inorganic alkaline agent be selected from the group consisting of ammonia; alkaline metal hydroxides; alkaline earth metal hydroxides; alkaline metal phosphates and monohydrogenophosphates such as sodium phosphate or sodium monohydrogenophosphate. It is also preferable that the inorganic alkaline agent be selected from inorganic ammonium salts such as ammonium carbonate and ammonium bicarbonate; and alkylammonium hydroxides such as
  • inorganic alkaline metal hydroxides mention may be made of sodium hydroxide and potassium hydroxide.
  • alkaline earth metal hydroxides mention may be made of calcium hydroxide and magnesium hydroxide.
  • sodium hydroxide is preferable.
  • the alkaline agent may be an organic alkaline agent. It is preferable that the organic alkaline agent be selected from the group consisting of monoamines and derivatives thereof; diamines and derivatives thereof; polyamines and derivatives thereof; basic amino acids and derivatives thereof; oligomers of basic amino acids and derivatives thereof; polymers of basic amino acids and derivatives thereof; urea and derivatives thereof; and guanidine and derivatives thereof.
  • organic alkaline agents examples include alkanolamines such as mono-, di- and tri-ethanolamine, and isopropanolamine; urea, guanidine and their derivatives; basic amino acids such as lysine, ornithine or arginine; and diamines such as those described in the structure below:
  • R denotes an alkylene such as propylene optionally substituted by a hydroxyl or a C C 4 alkyl radical, and R 1; R 2 , R 3 and R4 independently denote a hydrogen atom, an alkyl radical or a C 1 -C 4 hydroxyalkyl radical, which may be exemplified by 1,3-propanediamine and derivatives thereof. Arginine, urea and monoethanolamine are preferable.
  • the amount of the (c) alkaline agent in the composition may be from 0.01 to 15% by weight, preferably from 0.05 to 10% by weight, and more preferably from 0.1 to 8% by weight, relative to the total weight of the composition.
  • the pH of the composition according to the present invention may be 9.0 or less, preferably 8.9 or less, and more preferably 8.8 or less.
  • the pH of a composition comprising reducing agent(s) is relatively milder (lower) than that of conventional compositions for reshaping keratin fibers, the reshaping efficiency provided by the reducing agent(s) may be deteriorated.
  • the use of the (b) polyol can compensate for the deterioration of reshaping efficiency.
  • the composition according to the present invention can exert excellent reshaping efficiency even if the pH thereof is relatively milder.
  • the composition according to the present invention can further reduce the damage to keratin fibers.
  • the pH of the composition according to the present invention is 9.0 or less, preferably 8.9 or less, and more preferably 8.8 or less, the malodor caused by the reducing agent(s) and the like can be reduced.
  • the composition according to the present invention may have a pH of 7.0 or more. It is preferable that the pH of the composition according to the present invention be 7.2 or more, and more preferably 7.4 or more.
  • the pH of the composition according to the present invention may be from 7.0 to 9.0, preferably from 7.0 to 8.9, and more preferably from 7.0 to 8.8.
  • composition according to the present invention comprises water.
  • the amount of the water in the composition may be from 50 to 99% by weight, preferably from 60 to 95% by weight, and more preferably from 70 to 90% by weight, relative to the total weight of the composition.
  • composition according to the present invention may comprise (d) at least one surfactant.
  • Two or more (d) surfactants may be used.
  • a single type of surfactant or a combination of different types of surfactants may be used.
  • the (d) surfactant may be selected from the group consisting of anionic surfactants, amphoteric surfactants, cationic surfactants and nonionic surfactants. Two or more surfactants may be used in combination. Thus, a single type of surfactant or a combination of different types of surfactants may be used.
  • the amount of the (d) surfactant(s) may range from 0.01 to 10% by weight, preferably from 0.05 to 5% by weight, and more preferably from 0.1 to 1% by weight, relative to the total weight of the composition used in the process according to the present invention.
  • the composition may comprise at least one anionic surfactant. Two or more anionic surfactants may be used in combination.
  • anionic surfactant be selected from the group consisting of
  • the anionic surfactants are in the form of salts such as salts of alkali metals, for instance sodium; salts of alkaline-earth metals, for instance magnesium; ammonium salts; amine salts; and amino alcohol salts. Depending on the conditions, they may also be in acid form.
  • the anionic surfactant be selected from salts of (C -C 30 )alkyl sulfate, (C 6 -C 30 )alkyl ether sulfates or polyoxyalkylenated (C 6 -C 30 )alkyl ether carboxylic acid salified or not.
  • the composition may comprise at least one amphoteric surfactant. Two or more amphoteric surfactants may be used in combination.
  • amphoteric or zwitterionic surfactants can be, for example (non-limiting list), amine derivatives such as aliphatic secondary or tertiary amine, and optionally quaternized amine derivatives, in which the aliphatic radical is a linear or branched chain including 8 to 22 carbon atoms and containing at least one water-solubilizing anionic group (for example, carboxylate, sulphonate, sulphate, phosphate or phosphonate).
  • amine derivatives such as aliphatic secondary or tertiary amine
  • optionally quaternized amine derivatives in which the aliphatic radical is a linear or branched chain including 8 to 22 carbon atoms and containing at least one water-solubilizing anionic group (for example, carboxylate, sulphonate, sulphate, phosphate or phosphonate).
  • amphoteric surfactant may preferably be selected from the group consisting of betaines and amidoaminecarboxylated derivatives.
  • amphoteric surfactant be selected from betaine-type surfactants.
  • the betaine-type amphoteric surfactant is preferably selected from the group consisting of alkylbetaines, alkylamidoalkylbetaines, sulfobetaines, phosphobetaines, and
  • alkylamidoalkylsulfobetaines in particular, (C 8 -C 24 )alkylbetaines
  • amphoteric surfactants of betaine type are chosen from (C 8 -C 24 )alkylbetaines,
  • Non-limiting examples that may be mentioned include the compounds classified in the CTFA International Cosmetic Ingredient Dictionary & Handbook, 15th Edition, 2014, under the names cocobetaine, laurylbetaine, cetylbetaine, coco/oleamidopropylbetaine,
  • cocamidoethylbetaine cocamidopropylhydroxysultaine, oleamidopropylhydroxysultaine, cocohydroxysultaine, laurylhydroxysultaine, and cocosultaine, alone or as mixtures.
  • the betaine-type amphoteric surfactant is preferably an alkylbetaine and an
  • alkylamidoalkylbetaine in particular cocobetaine and cocamidopropylbetaine.
  • amidoaminecarboxylated derivatives mention may be made of the products sold under the name Miranol, as described in U.S. Pat. Nos. 2,528,378 and 2,781,354 and classified in the CTFA dictionary, 3rd edition, 1982 (the disclosures of which are incorporated herein by reference), under the names Amphocarboxyglycinates and
  • Ri denotes an alkyl radical of an acid Ri-COOH present in hydrolysed coconut oil, a heptyl, nonyl or undecyl radical,
  • R 2 denotes a beta-hydroxyethyl group
  • R 3 denotes a carboxymethyl group
  • M + denotes a cationic ion derived from alkaline metals such as sodium; ammonium ion; or an ion derived from an organic amine;
  • X denotes an organic or inorganic anionic ion such as halides, acetates, phosphates, nitrates, alkyl(C 1 -C4)sulfates, alkyl(C 1 -C 4 )- or alkyl(C 1 -C 4 )aryl-sulfonates, particularly methylsulfate and ethylsulfate; or M + and X " are not present; R 1 '-CONHCH 2 CH 2 -N(B)(C) (B2) in which:
  • R denotes an alkyl radical of an acid Ri'-COOH present in coconut oil or in hydrolysed linseed oil, an alkyl radical, such as a C 7 , C 9 , C or C 13 alkyl radical, a C 17 alkyl radical and its iso-form, or an unsaturated C 17 radical,
  • X' denotes a -CH 2 -COOH group, -CH 2 -COOZ', -CH 2 CH 2 -COOH, -CH 2 CH 2 -COOZ' or a hydrogen atom
  • Y' denotes -COOH, -COOZ', -CH 2 -CHOH-S0 3 Z ⁇ -CH 2 -CHOH-S0 3 H radical or a
  • Z' represents an ion of an alkaline or alkaline earth metal such as sodium, an ion derived from an organic amine or an ammonium ion;
  • Y denotes -C(0)OH, -C(0)OZ", -CH 2 -CH(OH)-S0 3 H or -CH 2 -CH(OH)-S0 3 -Z", wherein Z" denotes a cationic ion derived from alkaline metal or alkaline-earth metals such as sodium, an ion derived from organic amine or an ammonium ion;
  • Rd and Re denote a C 1 -C 4 alkyl or C C 4 hydroxyalkyl radical
  • R a denotes a C ! o-C 30 group alkyl or alkenyl group from an acid
  • n and n' independently denote an integer from 1 to 3.
  • amphoteric surfactant with formula Bl and B2 be selected from (Cg-C 24 )-alkyl amphomonoacetates, (C 8 -C 24 )alkyl amphodiacetates, (C 8 -C 24 )alkyl
  • Caprylamphodiacetate Disodium Capryloamphodiacetate, Disodium Cocoamphodipropionate, Disodium Lauroamphopropionate, Disodium Caprylamphodipropionate, Disodium
  • cocoamphodiacetate sold under the trade name Miranol® C2M concentrate by the company Rhodia Chimie.
  • CTFA diethylaminopropyl cocoaspartamide
  • the composition may comprise at least one cationic surfactant, Two or more cationic surfactants may be used in combination.
  • the cationic surfactant may be selected from the group consisting of optionally
  • quaternary ammonium salts examples include, but are not limited to:
  • R ls R 2 , R 3 , and R which may be identical or different, are chosen from linear and branched aliphatic radicals including from 1 to 30 carbon atoms and optionally including heteroatoms such as oxygen, nitrogen, sulfur and halogens.
  • the aliphatic radicals may be chosen, for example, from alkyl, alkoxy, C 2 -C 6 polyoxyalkylene, alkylamide,
  • R 5 is chosen from alkenyl and alkyl radicals including from 8 to 30 carbon atoms, for example fatty acid derivatives of tallow or of coconut;
  • R6 is chosen from hydrogen, Ci-C 4 alkyl radicals, and alkenyl and alkyl radicals including from 8 to 30 carbon atoms;
  • R 7 is chosen from C1-C4 alkyl radicals;
  • R is chosen from hydrogen and Q-C4 alkyl radicals
  • X " is chosen from halides, phosphates, acetates, lactates, alkyl sulfates, alkyl sulfonates, and alkylaryl sulfonates.
  • R 5 and are, for example, a mixture of radicals chosen from alkenyl and alkyl radicals including from 12 to 21 carbon atoms, such as fatty acid derivatives of tallow, R 7 is methyl and R 8 is hydrogen. Examples of such products include, but are not limited to, Quaternium-27 (CTFA 1997) and Quaternium-83 (CTFA 1997), which are sold under the names "Rewoquat®" W75, W90, W75PG and W75HPG by the company Witco;
  • R 9 is chosen from aliphatic radicals including from 16 to 30 carbon atoms
  • R 10 is chosen from hydrogen or alkyl radicals including from 1 to 4 carbon atoms or a group
  • Rn, R 12 , R 13 , R 14 , R 16a , R 17a , and R 18a which may be identical or different, are chosen from hydrogen and alkyl radicals including from 1 to 4 carbon atoms;
  • X " is chosen from halides, acetates, phosphates, nitrates, ethyl sulfates, and methyl sulfates.
  • diquaternary ammonium salt is FINQUAT CT-P of FINETEX
  • R 22 is chosen from Ci-C 6 alkyl radicals and Cj-C 6 hydroxyalkyl and dihydroxyalkyl radicals;
  • R 23 is chosen from:
  • R 25 is chosen from:
  • R24, R26, and R 2 8 which may be identical or different, are chosen from linear and branched, saturated and unsaturated, C 7 -C 21 , hydrocarbon-based radicals;
  • x and z which may be identical or different, are chosen from integers ranging from 0 to 10;
  • X " is chosen from simple and complex, organic and inorganic anions; with the proviso that the sum x+y+z ranges from 1 to 15, that when x is 0, R 23 denotes R 27 , and that when z is 0, R 25 denotes R 29 .
  • R22 may be chosen from linear and branched alkyl radicals. In one embodiment, R 22 is chosen from linear alkyl radicals. In another embodiment, R 22 is chosen from methyl, ethyl, hydroxyethyl, and dihydroxypropyl radicals, for example methyl and ethyl radicals.
  • the sum x+y+z ranges from 1 to 10.
  • R 23 is a hydrocarbon-based radical R 2
  • R 25 is a hydrocarbon-based radical R 29
  • R 24 , R 26 , and R 28 which may be identical or different, are chosen from linear and branched, saturated and unsaturated, Cn-C 21 hydrocarbon-based radicals, for example from linear and branched, saturated and unsaturated Cu-C 21 alkyl and alkenyl radicals.
  • x and z which may be identical or different, are 0 or 1.
  • y is equal to 1.
  • r, s and t which may be identical or different, are equal to 2 or 3, for example equal to 2.
  • the anion X " may be chosen from, for example, halides, such as chloride, bromide, and iodide; and C C 4 alkyl sulfates, such as methyl sulfate.
  • methanesulfonate, phosphate, nitrate, tosylate, an anion derived from an organic acid, such as acetate and lactate, and any other anion that is compatible with the ammonium including an ester function are other non-limiting examples of anions that may be used according to the present invention.
  • the anion X " is chosen from chloride and methyl sulfate.
  • ammonium salts of formula (B6) may be used, wherein:
  • R 22 is chosen from methyl and ethyl radicals
  • x and y are equal to 1 ;
  • z is equal to 0 or 1 ;
  • r, s and t are equal to 2;
  • R23 is chosen from:
  • R 25 is chosen from:
  • R24, R26, and R 28 which may be identical or different, are chosen from linear and branched, saturated and unsaturated, C 13 -C 17 hydrocarbon-based radicals, for example from linear and branched, saturated and unsaturated, C 13 -C 17 alkyl and alkenyl radicals.
  • the hydrocarbon-based radicals are linear.
  • Non-limiting examples of compounds of formula (B6) that may be mentioned include salts, for example chloride and methyl sulfate, of diacyloxyethyl-dimethylammonium, of
  • the acyl radicals may include from 14 to 18 carbon atoms, and may be derived, for example, from a plant oil, for instance palm oil and sunflower oil. When the compound includes several acyl radicals, these radicals may be identical or different.
  • alkyldiisopropanolamine onto fatty acids or onto mixtures of fatty acids of plant or animal origin, or by transesterification of the methyl esters thereof.
  • This esterification may be followed by a quatemization using an alkylating agent chosen from alkyl halides, for example methyl and ethyl halides; dialkyl sulfates, for example dimethyl and diethyl sulfates; methyl methanesulfonate; methyl para-toluenesulfonate; glycol chlorohydrin; and glycerol
  • Such compounds are sold, for example, under the names Dehyquart® by the company Cognis, Stepanquat® by the company Stepan, Noxamium® by the company Ceca, and "Rewoquat® WE 18" by the company Rewo-Goldschmidt.
  • ammonium salts that may be used in the composition according to the present invention include the ammonium salts including at least one ester function described in U.S. Pat. Nos. 4,874,554 and 4,137,180.
  • quaternary ammonium salts mentioned above that may be used in the composition according to the present invention include, but are not limited to, those corresponding to formula (I), for example tetraalkylammonium chlorides, for instance
  • dialkyldimethylammonium and alkyltrimethylammonium chlorides in which the alkyl radical includes from about 12 to 22 carbon atoms, such as behenyltrimethylammonium,
  • the cationic surfactant that may be used in the composition according to the present invention is chosen from behenyltrimethylammonium chloride, cetyltrimethylammonium chloride, Quaternium-83, Quaternium-87, Quaternium-22, behenylamidopropyl-2,3-dihydroxypropyldimethylammonium chloride,
  • palmitylamidopropyltrimethylammonium chloride and stearamidopropyldimethylamine.
  • the composition comprises at least one nonionic surfactant.
  • Two or more nonionic surfactants may be used in combination.
  • the nonionic surfactants are compounds well known in themselves (see, e.g., in this regard, "Handbook of Surfactants” by M. R. Porter, Blackie & Son publishers (Glasgow and London), 1991, pp. 116-178).
  • they can, for example, be chosen from alcohols, alpha-diols, alkylphenols and esters of fatty acids, these compounds being ethoxylated, propoxylated or glycerolated and having at least one fatty chain comprising, for example, from 8 to 30 carbon atoms, it being possible for the number of ethylene oxide or propylene oxide groups to range from 2 to 50, and for the number of glycerol groups to range from 1 to 30.
  • Maltose derivatives may also be mentioned.
  • amine oxides such as (C 1 o-C 14 )alkylamine oxides or N-(C 10 -C 14 )acylaminopropylmorpholine oxides; silicone surfactants; and mixtures thereof.
  • the nonionic surfactants may preferably be chosen from monooxyalkylenated,
  • polyoxyalkylenated, monoglycerolated or polyglycerolated nonionic surfactants are more particularly oxyethylene or oxypropylene units, or a combination thereof, and are preferably oxyethylene units.
  • monooxyalkylenated or polyoxyalkylenated nonionic surfactants include:
  • esters of saturated or unsaturated, linear or branched, C 8 -C 30 acids and of polyalkylene glycols are examples of esters of saturated or unsaturated, linear or branched, C 8 -C 30 acids and of polyalkylene glycols,
  • the surfactants preferably contain a number of moles of ethylene oxide and/or of propylene oxide of between 1 and 100 and most preferably between 2 and 50.
  • the polyoxyalkylenated nonionic surfactants are chosen from polyoxyethylenated fatty alcohol (polyethylene glycol ether of fatty alcohol) and polyoxyethylenated fatty ester (polyethylene glycol ester of fatty acid).
  • polyoxyethylenated saturated fatty alcohol examples include the adducts of ethylene oxide with lauryl alcohol, especially those containing from 9 to 50 oxyethylene units and more particularly those containing from 10 to 12 oxyethylene units (Laureth-10 to Laureth-12, as the CTFA names); the adducts of ethylene oxide with behenyl alcohol, especially those containing from 9 to 50 oxyethylene units (Beheneth-9 to Beheneth-50, as the CTFA names); the adducts of ethylene oxide with cetearyl alcohol (mixture of cetyl alcohol and stearyl alcohol), especially those containing from 10 to 30 oxyethylene units (Ceteareth-10 to Ceteareth-30, as the CTFA names); the adducts of ethylene oxide with cetyl alcohol, especially those containing from 10 to 30 oxyethylene units (Ceteth-10 to Ceteth-30, as the CTFA names); the adducts of ethylene oxide with cetyl alcohol, especially those containing from 10 to
  • Steareth-30 as the CTFA names
  • the adducts of ethylene oxide with isostearyl alcohol especially those containing from 10 to 50 oxyethylene units (Isosteareth-10 to Isosteareth-50, as the CTFA names); and mixtures thereof.
  • polyoxyethylenated unsaturated fatty alcohol (or C 8 -C 30 alcohols) include the adducts of ethylene oxide with oleyl alcohol, especially those containing from 2 to 50 oxyethylene units and more particularly those containing from 10 to 40 oxyethylene units (Oleth-10 to Oleth-40, as the CTFA names); and mixture thereof.
  • monoglycerolated or polyglycerolated nonionic surfactants examples include the adducts of ethylene oxide with oleyl alcohol, especially those containing from 2 to 50 oxyethylene units and more particularly those containing from 10 to 40 oxyethylene units (Oleth-10 to Oleth-40, as the CTFA names).
  • monoglycerolated or polyglycerolated C -C 40 alcohols are preferably used.
  • the monoglycerolated or polyglycerolated C -C 4 o alcohols correspond to the following formula:
  • lauryl alcohol containing 4 mol of glycerol (INCI name: Polyglyceryl-4 Lauryl Ether), lauryl alcohol containing 1.5 mol of glycerol, oleyl alcohol containing 4 mol of glycerol (INCI name: Polyglyceryl-4 Oleyl Ether), oleyl alcohol containing 2 mol of glycerol (INCI name: Polyglyceryl-2 Oleyl Ether), cetearyl alcohol containing 2 mol of glycerol, cetearyl alcohol containing 6 mol of glycerol, oleocetyl alcohol containing 6 mol of glycerol, and octadecanol containing 6 mol of glycerol.
  • the alcohol may represent a mixture of alcohols in the same way that the value of m represents a statistical value, which means that, in a commercial product, several species of polyglycerolated fatty alcohol may coexist in the form of a mixture.
  • the C /C 10 alcohol containing 1 mol of glycerol it is preferable to use the C /C 10 alcohol containing 1 mol of glycerol, the C 10 /C 12 alcohol containing 1 mol of glycerol and the C 12 alcohol containing 1.5 mol of glycerol.
  • the monoglycerolated or polyglycerolated C -C 40 fatty esters may correspond to the following formula: R'0-[CH 2 -CH(CH 2 OR'")-0] m -R" or R'0-[CH(CH 2 OR'")-CH 2 0] m -R" in which each of R', R" and R"' independently represents a hydrogen atom, or a linear or branched C 8 -C 40 and preferably C -C 3 o alkyl-CO- or alkenyl-CO-radical, with the proviso that at least one of R', R" and R'" is not a hydrogen atom, and m represents a number ranging from 1 to 30 and preferably from 1.5 to 10.
  • polyoxyethylenated fatty esters examples include the adducts of ethylene oxide with esters of lauric acid, palmitic acid, stearic acid or behenic acid, and mixtures thereof, especially those containing from 9 to 100 oxyethylene units, such as PEG-9 to PEG-50 laurate (CTFA names: PEG-9 laurate to PEG-50 laurate); PEG-9 to PEG-50 palmitate (CTFA names: PEG-9 palmitate to PEG-50 palmitate); PEG-9 to PEG-50 stearate (CTFA names: PEG-9 stearate to PEG-50 stearate); PEG-9 to PEG-50 palmitostearate; PEG-9 to PEG-50 behenate (CTFA names: PEG-9 behenate to PEG-50 behenate); polyethylene glycol 100 EO monostearate (CTFA name: PEG- 100 stearate); and mixtures thereof.
  • CTFA names: PEG-9 laurate to PEG-50 laurate PEG-9 to PEG-50
  • the nonionic surfactant may be selected from esters of polyols with fatty acids with a saturated or unsaturated chain containing for example from 8 to 24 carbon atoms, preferably 12 to 22 carbon atoms, and polyoxyalkylenated derivatives thereof, preferably containing from 10 to 200, and more preferably from 10 to 100 oxyalkylene units, such as glyceryl esters of a C -C 24 , preferably C 12 -C 22 , fatty acid or acids and polyoxyalkylenated derivatives thereof, preferably containing from 10 to 200, and more preferably from 10 to 100 oxyalkylene units; sorbitol esters of a C 8 -C 2 4, preferably C 12 -C 22 , fatty acid or acids and polyoxyalkylenated derivatives thereof, preferably containing from 10 to 200, and more preferably from 10 to 100 oxyalkylene units; sugar (sucrose, maltose, glucose, fruct
  • glyceryl esters of fatty acids glyceryl stearate (glyceryl mono-, di- and/or tristearate) (CTFA name: glyceryl stearate), glyceryl laurate or glyceryl ricinoleate and mixtures thereof can be cited, and as polyoxyalkylenated derivatives thereof, mono-, di- or triester of fatty acids with a polyoxyalkylenated glycerol (mono-, di- or triester of fatty acids with a polyalkylene glycol ether of glycerol), preferably polyoxyethylenated glyceryl stearate
  • surfactants such as for example the product containing glyceryl stearate and PEG- 100 stearate, marketed under the name ARLACEL 165 by Uniqema, and the product containing glyceryl stearate (glyceryl mono- and distearate) and potassium stearate marketed under the name TEGIN by Goldschmidt (CTFA name: glyceryl stearate SE), can also be used.
  • the sorbitol esters of C 8 -C 24 fatty acids and polyoxyalkylenated derivatives thereof can be selected from sorbitan palmitate, sorbitan isostearate, sorbitan trioleate and esters of fatty acids and alkoxylated sorbitan containing for example from 20 to 100 EO, such as for example sorbitan monostearate (CTFA name: sorbitan stearate), sold by the company ICI under the name Span 60, sorbitan monopalmitate (CTFA name: sorbitan palmitate), sold by the company ICI under the name Span 40, and sorbitan tristearate 20 EO (CTFA name:
  • polysorbate 65 sold by the company ICI under the name Tween 65, polyethylene sorbitan trioleate (polysorbate 85) or the compounds marketed under the trade names Tween 20 or Tween 60 by Uniqema.
  • esters of fatty acids and glucose or alkylglucose glucose palmitate, alkylglucose sesquistearates such as methylglucose sesquistearate, alkylglucose palmitates such as methylglucose or ethylglucose palmitate, methylglucoside fatty esters, the diester of methylglucoside and oleic acid (CTFA name: Methyl glucose dioleate), the mixed ester of methylglucoside and the mixture of oleic acid/hydroxystearic acid (CTFA name: Methyl glucose dioleate/hydroxystearate), the ester of methylglucoside and isostearic acid (CTFA name: Methyl glucose isostearate), the ester of methylglucoside and lauric acid (CTFA name: Methyl glucose laurate), the mixture of monoester and diester of methylglucoside and isostearic acid (CTFA name: Methyl
  • ethoxylated ethers of fatty acids and glucose or alkylglucose ethoxylated ethers of fatty acids and methylglucose, and in particular the polyethylene glycol ether of the diester of methylglucose and stearic acid with about 20 moles of ethylene oxide (CTFA name: PEG-20 methyl glucose distearate) such as the product marketed under the name Glucam E-20 distearate by AMERCHOL, the polyethylene glycol ether of the mixture of monoester and diester of methyl-glucose and stearic acid with about 20 moles of ethylene oxide (CTFA name: PEG-20 methyl glucose sesquistearate) and in particular the product marketed under the name Glucamate SSE-20 by AMERCHOL and that marketed under the name Grillocose PSE-20 by GOLDSCHMIDT, and mixtures thereof, can for example be cited.
  • sucrose esters As sucrose esters, saccharose palmito-stearate, saccharose stearate and saccharose
  • alkylpolyglucosides can be used, and for example decylglucoside such as the product marketed under the name MYDOL 10 by Kao Chemicals, the product marketed under the name PLANTAREN 2000 by Henkel, and the product marketed under the name
  • ORAMIX NS 10 by Seppic caprylyl/capryl glucoside such as the product marketed under the name ORAMIX CG 110 by Seppic or under the name LUTENSOL GD 70 by BASF, laurylglucoside such as the products marketed under the names PLANTAREN 1200 N and PLANTACARE 1200 by Henkel, coco-glucoside such as the product marketed under the name PLANTACARE 818 UP by Henkel, cetostearyl glucoside possibly mixed with cetostearyl alcohol, marketed for example under the name MONTANOV 68 by Seppic, under the name TEGO-CARE CG90 by Goldschmidt and under the name EMULGADE KE3302 by Henkel, arachidyl glucoside, for example in the form of the mixture of arachidyl and behenyl alcohols and arachidyl glucoside marketed under the name MONTANOV 202 by Seppic, cocoylethylglucoside, for example in
  • glycerides of alkoxylated plant oils such as mixtures of ethoxylated (200 EO) palm and copra (7 EO) glycerides can also be cited.
  • the nonionic surfactant according to the present invention preferably contains alkenyl or a branched C 12 -C 22 acyl chain such as an oleyl or isostearyl group. More preferably, the nonionic surfactant according to the present invention is PEG-20 glyceryl triisostearate.
  • the nonionic surfactant may be selected from copolymers of ethylene oxide and of propylene oxide, in particular copolymers of the following formula: HO(C 2 H 4 0) a (C 3 H 6 0) b (C 2 H 4 0) c H in which a, b and c are integers such that a+c ranges from 2 to 100 and b ranges from 14 to 60, and mixtures thereof.
  • the nonionic surfactant may be selected from silicone surfactants.
  • silicone surfactants Non-limiting mention may be made of those disclosed in documents US-A-5364633 and US-A-5411744.
  • the silicone surfactant may preferably be a compound of formula (I):
  • R l3 R 2 and R 3 independently of each other, represent a Ci-C ⁇ alkyl radical or a radical
  • R R 2 or R 3 not being an alkyl radical
  • R4 being a hydrogen, an alkyl radical or an acyl radical
  • A is an integer ranging from 0 to 200;
  • B is an integer ranging from 0 to 50; with the proviso that A and B are not simultaneously equal to zero;
  • x is an integer ranging from 1 to 6;
  • y is an integer ranging from 1 to 30;
  • z is an integer ranging from 0 to 5.
  • the alkyl radical is a methyl radical
  • x is an integer ranging from 2 to 6
  • y is an integer ranging from 4 to 30.
  • silicone surfactants of formula (I) mention may be made of the compounds of formula (II):
  • A is an integer ranging from 20 to 105
  • B is an integer ranging from 2 to 10
  • y is an integer ranging from 10 to 20.
  • silicone surfactants of formula (I) mention may also be made of the compounds of formula (III):
  • DC 5329, DC 7439-146, DC 2-5695 and Q4-3667 are compounds of formula (II) in which, respectively, A is 22, B is 2 and y is 12; A is 103, B is 10 and y is 12; A is 27, B is 3 and y is 12.
  • the compound Q4-3667 is a compound of formula (III) in which A is 15 and y is 13.
  • the composition according to the present invention may comprise at least one acid. Two or more acids may be used in combination. Thus, a single type of acid or a combination of different types of acids may be used.
  • the acid may be used to adjust the pH of the composition according to the present invention.
  • the composition according to the present invention include acid(s), if necessary, to control the pH of the composition to be 9.0 or less, preferably 8.9 or less, and more preferably 8.8 or less.
  • acid mention may be made of any inorganic or organic acids which are commonly used in cosmetic products such as citric acid, lactic acid, sulfuric acid, phosphoric acid or hydrochloric acid (HC1). HC1 is preferable.
  • the acid(s) may be used in a total amount of from 0.1 to 15% by weight, preferably from 0.2 to 10% by weight, more preferably from 0.3 to 5% by weight, relative to the total weight of the composition, depending on their solubility.
  • the composition according to the present invention may comprise at least one amino acid other than the above reducing agent, alkaline agent or acid. Two or more amino acids may be used in combination. Thus, a single type of amino acid or a combination of different types of amino acids may be used.
  • amino acid here means a compound which is not obtained by polycondensation of identical or different amino acids.
  • amino acid here encompasses not only an amino acid itself but also an amino acid in the form of a salt thereof. As the salt, mention may be made of sodium salt, magnesium salt, potassium salt, calcium salt, and the like.
  • amino acids that may be used according to the present invention comprise at least one amine function and at least one acid function.
  • the acid function(s) may be carboxylic, sulfonic, phosphonic or phosphoric, and are preferably carboxylic.
  • amino acids that may be used according to the present invention may be a-amino acids, ⁇ -amino acids, or ⁇ -amino acids.
  • amino acids used in the present invention are a-amino acids, i.e., they comprise an amine function and an acid function at the same carbon atom.
  • the ⁇ -amino acids may be represented by the following formula:
  • R represents a hydrogen atom, an aliphatic group optionally containing one or several nitrogen atoms, a heterocyclic portion, or an aromatic group, or
  • This heterocycle is preferably a saturated 5-membered ring, optionally substituted with one or more C 1-4 alkyl or hydroxyl groups.
  • the aliphatic group is a linear or branched C 1-4 alkyl group; a linear or branched C 1-4 hydroxyalkyl group; a linear or branched C 1-4 aminoalkyl group; a linear or branched (C 1-4 alkyl)thio(C 1- 4)alkyl group; a linear or branched C 2-4 carboxyalkyl group; a linear or branched ureidoalkyl group, a linear or branched guanidinoalkyl group, a linear or branched imidazoloalkyl group or a linear or branched indolylalkyl group, the alkyl portions of these last four groups comprising from one to four carbon atoms.
  • the aromatic group is a C 6 aryl or C 7-10 aralkyl group, the aromatic nucleus optionally being substituted with one or more C 1-4 alkyl or hydroxyl groups.
  • amino acids that may be used in the present invention, mention may be made especially of aspartic acid, glutamic acid, alanine, asparagine, carnitine, glutamine, glycine, histidine, isoleucine, leucine, methionine, N-phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine, valine, hydroxyproline and mixtures thereof.
  • the amino acids comprise only one amine function, which may or may not be engaged in a ring, and only one acid function.
  • the amino acids that are particularly preferred in the present invention are alanine, asparagine, glutamine, glycine, isoleucine, leucine, methionine, N-phenylalanine, proline, serine, threonine, tyrosine and valine.
  • the aminoacid(s) may be used in a total amount of from 0.001 to 10% by weight, preferably from 0.05 to 5% by weight, more preferably from 0.01 to 1% by weight, relative to the total weight of the composition.
  • composition according to the present invention may comprise at least one conditioning agent.
  • Two or more conditioning agents may be used in combination.
  • a single type of conditioning agent or a combination of different types of conditioning agents may be used.
  • the conditioning agent can provide keratin fibers such as hair with conditioning effects.
  • the conditioning agent be selected from cationic polymers.
  • the composition according to the present invention may comprise at least one cationic polymer.
  • a single type of cationic polymer may be used, but two or more different types of cationic polymers may be used in combination.
  • the term "cationic polymer” denotes any polymer containing cationic groups and/or groups that may be ionized into cationic groups.
  • Such polymers may be chosen from those already known per se as improving the cosmetic properties of the hair, i.e., especially those described in patent application EP-A-337 354 and in French patents FR-2 270 846, 2 383 660, 2 598 611 , 2 470 596 and 2 519 863.
  • the cationic polymers that are preferred are chosen from those containing units comprising primary, secondary, tertiary and/or quaternary amine groups, which may either form part of the main polymer chain or may be borne by a side substituent directly attached thereto.
  • the cationic polymers used generally have a number-average molecular mass of between approximately 500 and approximately 5 ⁇ 10 6 and preferably between approximately 10 3 and approximately 3 ⁇ 10 6 .
  • cationic polymers that may be mentioned more particularly are polymers of the polyamine, polyamino amide and polyquaternary ammonium type.
  • R-3 which may be identical or different, denote a hydrogen atom or a CH 3 radical
  • A which may be identical or different, represent a linear or branched alkyl group of 1 to
  • R4, R 5 and R ⁇ which may be identical or different, represent an alkyl group containing from 1 to 18 carbon atoms or a benzyl radical and preferably an alkyl group containing from 1 to 6 carbon atoms;
  • R ⁇ and R 2 which may be identical or different, represent hydrogen or an alkyl group containing from 1 to 6 carbon atoms, and preferably methyl or ethyl;
  • X denotes an anion derived from an inorganic or organic acid, such as a methosulfate anion or a halide such as chloride or bromide.
  • the polymers of family (1) can also contain one or more units derived from comonomers which may be chosen from the family of acrylamides, methacrylamides, diacetone
  • Cationic cellulose derivatives such as the copolymers of cellulose or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer, described especially in US patent 4 131 576, such as hydroxyalkylcelluloses, for instance hydroxymethyl-,
  • the commercial products corresponding to this definition are more particularly the products sold under the name Celquat L 200 and Celquat H 100 by the company Akzo Nobel.
  • guar gums containing trialkylammonium cationic groups such as guar gums containing trialkylammonium cationic groups.
  • Use is made, for example, of guar gums modified with a salt (e.g., chloride) of
  • hydroxypropyltrimonium chloride and hydroxypropyl guar hydroxypropyl trimonium chloride such as those sold especially under the trade names Jaguar C13S, Jaguar CMS, Jaguar C 17 and Jaguar C 162 by the company Solvay.
  • Cyclopolymers of alkyldiallylamine or of dialkyldiallylammonium such as the homopolymers or copolymers containing, as a main constituent of the chain, units
  • R 9 denotes a hydrogen atom or a methyl radical
  • R 7 and R 8 independently of each other, denote an alkyl group having from 1 to 6 carbon atoms, a hydroxyalkyl group in which the alkyl group preferably has 1 to 5 carbon atoms, a lower (C 1 -C 4 ) amidoalkyl group, or R 7 and R 8 can denote, together with the nitrogen atom to which they are attached, heterocyclic groups such as piperidyl or morpholinyl
  • R 7 and R 8 independently of each other, preferably denote an alkyl group having from 1 to 4 carbon atoms
  • Y " is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulfate, bisulfite, sulfate or phosphate.
  • R 10 , n, R 12 and R 13 which may be identical or different, represent aliphatic, alicyclic or arylaliphatic radicals containing from 1 to 20 carbon atoms or lower hydroxyalkylaliphatic radicals, or alternatively R 10 , R 11; R 12 and R 13 , together or separately, constitute, with the nitrogen atoms to which they are attached, heterocycles optionally containing a second hetero atom other than nitrogen, or alternatively R 10 , Ru, R 12 and R 13 represent a linear or branched C C 6 alkyl radical substituted with a nitrile, ester, acyl or amide group or a group
  • Ai and Bi represent polymethylene groups containing from 2 to 20 carbon atoms which may be linear or branched, saturated or unsaturated, and which may contain, linked to or intercalated in the main chain, one or more aromatic rings or one or more oxygen or sulfur atoms or sulfoxide, sulfone, disulfide, amino, alkylamino, hydroxyl, quaternary ammonium, ureido, amide or ester groups, and
  • X denotes an anion derived from an inorganic or organic acid
  • Ai, R 10 and R 12 can form, with the two nitrogen atoms to which they are attached, a piperazine ring; in addition, if Ai denotes a linear or branched, saturated or unsaturated alkylene or hydroxyalkylene radical, Bi can also denote a group -(CH 2 ) n -CO-D-OC-(CH 2 ) n - in which D denotes:
  • hydrocarbon-based radical or a group corresponding to one of the following formulae:
  • x and y denote an integer from 1 to 4, representing a defined and unique degree of polymerization or any number from 1 to 4 representing an average degree of polymerization; ii) a bis-secondary diamine residue such as a piperazine derivative;
  • X " is an anion such as chloride or bromide.
  • These polymers generally have a number-average molecular mass of between 1000 and 100 000.
  • Rio, Rn, Ri2 and R 13 which may be identical or different, denote an alkyl or hydroxyalkyl radical containing from 1 to 4 carbon atoms approximately, n and p are integers ranging from 2 to 20 approximately, and X " is an anion derived from a mineral or organic acid.
  • acrylamide/methacryloyloxyethyltrimethylammonium chloride copolymer (20/80 by weight) in the form of a dispersion containing 50% by weight of the said copolymer in mineral oil can be used more particularly.
  • This dispersion is sold under the name "Salcare® SC 92" by the company BASF.
  • a crosslinked methacryloyloxyethyltrimethylammonium chloride homopolymer containing about 50% by weight of the homopolymer in mineral oil or in a liquid ester can also be used.
  • These dispersions are sold under the names "Salcare® SC 95" and "Salcare® SC 96" by the company Allied Colloids.
  • cationic polymers which can be used in the context of the present invention are polyalkyleneimines, in particular polyethyleneimines, polymers containing vinylpyridine or vinylpyridinium units, condensates of polyamines and of epichlorohydrin, quaternary polyureylenes and chitin derivatives. It is preferable that the cationic polymer be a polyquaternium polymer or a polymeric quaternary ammonium salt.
  • Polymeric quaternary ammonium salts are cationic polymers comprising at least one quaternized nitrogen atom. Mention may in particular be made, as polymeric quaternary ammonium salts, of the Polyquaternium products (CTFA name), which contribute mainly to the quality of foam and feeling of the skin after use, in particular the feeling of the skin after use.
  • CTFA name Polyquaternium products
  • These polymers can preferably be chosen from the following polymers:
  • Polyquaternium-5 such as the product Merquat 5 sold by Nalco;
  • Polyquaternium-6 such as the product Salcare SC 30 sold by BASF and the product Merquat 100 sold by Nalco;
  • Polyquaternium-7 such as the products Merquat S, Merquat 2200, Merquat 7SPR, and
  • Polyquaternium-ll such as the products Gafquat 755, Gafquat 755N and Gafquat 734 sold by ISP;
  • Polyquaternium- 16 such as the products Luviquat FC905, Luviquat FC370, Luviquat HM552 and Luviquat FC550 sold by BASF;
  • Polyquaternium-28 such as the product Styleze CC 10 sold by ISP;
  • Polyquaternium-44 such as the product Luviquat Care sold by BASF
  • Polyquaternium-46 such as the product Luviquat Hold sold by BASF
  • Polyquaternium-47 such as the product Merquat 2001 sold by Nalco.
  • the cationic polymer is chosen from, Polyquaternium-10, Polyquaternium-47, hydroxypropyl guar hydroxypropyl trimonium chloride and their mixtures.
  • the amount of the cationic polymer(s) is not limited, but the amount of the cationic polymer may be from 0.01 to 10% by weight, preferably 0.05 to 5% by weight, and more preferably 0.1 to 1% by weight, relative to the total weight of the composition.
  • composition according to the present invention may be free of dicarboxylic acid which is present as it is (i.e., dicarboxylic acid itself or a salt thereof).
  • dicarboxylic acid mention may be made of ⁇ , ⁇ -dicarboxylic acid with 5 to 10 carbon atoms, and preferably adipic acid.
  • composition according to the present invention may also comprise at least one additional ingredient.
  • the amount of the additional ingredient(s) is not limited, but may be from 0.1 to 10% by weight relative to the total weight of the composition according to the present invention.
  • the additional ingredient(s) may be selected from the group consisting of thickeners; anionic, nonionic or amphoteric polymers; peptides and derivatives thereof; protein hydrolyzates; swelling agents and penetrating agents; agents for combating hair loss; anti-dandruff agents; associative-type or not, natural or synthetic thickeners for oils; suspending agents;
  • sequestering agents include opacifying agents; dyes; sunscreen agents; vitamins or provitamins; fragrances; preserving agents, stabilizers; and mixtures thereof.
  • the vehicle for the composition according to the present invention is preferably an aqueous medium consisting of water and may advantageously contain one or several cosmetically acceptable organic solvents, which particularly include monohydric alcohols, such as ethyl alcohol, isopropyl alcohol, benzyl alcohol and phenylethyl alcohol, as well as ethylene glycol alkyl ethers such as ethylene glycol monomethyl, monoethyl and monobutyl ethers; propylene glycol alkyl ethers such as propylene glycol monomethyl, monoethyl and monomutyl ethers; diethylene glycol alkyl ethers such as diethylene glycol monomethyl, monoethyl and monobutyl ethers.
  • monohydric alcohols such as ethyl alcohol, isopropyl alcohol, benzyl alcohol and phenylethyl alcohol
  • ethylene glycol alkyl ethers such as ethylene glycol monomethyl, monoethyl and monobutyl ethers
  • the present invention also relates to a reshaping process, in particular permanent waving, for keratin fibers, preferably the hair.
  • the reshaping process according to the present invention can be performed by: (i) applying onto keratin fibers the composition described above;
  • the step (i) is for reducing the disulfide bonds in keratin fibers.
  • composition used in the step (i) for reducing the disulfide bonds in keratin fibers can be used as a permanent waving composition for the keratin fibers.
  • the above-described composition is applied to the keratin fibers.
  • the application of the composition may be performed by any means, such as a brush and a comb. It may be possible that the keratin fibers after the application of the composition be left as they are for a certain amount of time typically from 1 minute to 1 hour, preferably from 10 to 40 minutes, if necessary, in order to let the composition penetrate into the keratin fibers.
  • the keratin fibers may be rinsed preferably with water.
  • keratin fibers such as hair may be subjected to mechanical tension which is typically used for permanent deformation of the keratin fibers before and/or after the step (i), preferably before the step (iii).
  • the mechanical tension can be applied to the keratin fibers by any means to deform the keratin fibers to an intended shape.
  • the mechanical tension may be provided by at least one reshaping means selected from the group consisting of a curler, a roller, and a clip.
  • the reshaping means may comprise at least one heater. If the keratin fibers are rolled around a curler, this rolling-up may be performed on the entire length of the keratin fibers or, for example, on half the length of the keratin fibers. Depending on, for example, the desired hairstyle shape and amount of curls, the rolling-up may be performed with more or less thick locks.
  • the keratin fibers may be provided with heat, for deforming or reshaping the keratin fibers, preferably after the step (i) or the step (ii) if present, or before the step (iii).
  • the keratin fibers which may or may not be under mechanical tension are heated with a heating means such as a heating iron (when straightening) or a heating rod (when waving) at typically from 50 to 150°C, preferably 70 to 100°C for typically 5 minutes to 2 hours, preferably 10 minutes to 1 hour.
  • the keratin fibers are oxidized by an oxidizing composition.
  • the oxidizing composition comprises at least one oxidizing agent.
  • the oxidizing agent(s) is (are) chosen from hydrogen peroxide, urea peroxide, alkali metal bromates or ferricyanides, and peroxygenated salts, for instance alkali metal or alkaline-earth metal persulfates, perborates and percarbonates, and peracids and precursors thereof
  • the oxidizing composition comprise sodium bromate, especially as an aqueous solution thereof (aqueous sodium bromate solution).
  • concentration of the sodium bromate in the oxidizing composition may range from 0.1 to 20% by weight, preferably 1 to 10% by weight, relative to the total weight of the oxidizing composition.
  • the oxidizing composition comprises hydrogen peroxide, especially as an aqueous solution thereof (aqueous hydrogen peroxide solution).
  • concentration of the hydrogen peroxide in the oxidizing composition may range from 0.1 to 20% by weight, preferably 1 to 10% by weight, relative to the total weight of the oxidizing composition.
  • the oxidizing composition may be aqueous or nonaqueous.
  • aqueous means that the developer comprises more than 5% by weight of water, preferably more than 10% by weight of water and even more advantageously more than 20% by weight of water.
  • the pH of the oxidizing composition when it is aqueous, is less than 8.
  • the oxidizing composition may also contain at least one additional ingredient explained in detail previously in the context of the composition according to the present invention.
  • the oxidizing composition may be in various forms, for instance a shampoo, a gel, a mousse, a thickened lotion and a cream.
  • the step (iii) perform mild oxidation by applying an oxidizing composition with a short, or with no, standing time on the keratin fibers.
  • an oxidizing composition with a short, or with no, standing time on the keratin fibers.
  • the standing time mention may be made of 3 minutes to 40 minutes, preferably 5 minutes to 30 minutes.
  • the keratin fibers may be rinsed preferably with water, and/or may be dried.
  • the drying of the keratin fibers can be performed with a conventional drying means such as a hair drier.
  • the present invention also relates to a method for enhancing reshaping efficiency of keratin fibers with less damage to the keratin fibers provided by a reducing composition comprising at least one reducing agent in combination with an oxidizing composition comprising at least one oxidizing agent, characterized by adding at least one polyol with 4 or more carbon atoms to the reducing composition in an amount of less than 1.0% by weight relative to the total weight of the reducing composition.
  • the present invention also relates to a use of at least one polyol with 4 or more carbon atoms in a reducing composition comprising at least one reducing agent wherein the amount of the polyol in the reducing composition is less than 1.0% by weight relative to the total weight of the reducing composition, for enhancing reshaping efficiency for keratin fibers with less damage to the keratin fibers provided by the reducing composition in combination with an oxidizing composition comprising at least one oxidizing agent.
  • the polyol can promote the penetration of the reducing agent(s) into keratin fibers, and can reduce or cancel hydrophobic interactions that are non-reactive bonds in the keratin fibers. Due to the use of the polyol with the reducing agent(s), cancellation of the internal bonds in the keratin fibers can be performed even with a small amount of the reducing agent(s).
  • the polyol used in the present invention is not intended for conditioning keratin fibers.
  • the amount of polyol used in the present invention is limited such that it is less than 1.0% by weight relative to the total weight of the composition.
  • the use of the polyol in an amount of 1.0% by weight or more, preferably 1.5% by weight or more, and more preferably 2.0% by weight or more, relative to the total weight of the composition is not preferable, because the reshaping efficiency of the keratin fibers can be deteriorated.
  • compositions according to Examples 1-11 and Comparative Examples 1-7 shown in Tables 1 and 2 were prepared by mixing the ingredients shown in Tables 1 and 2.
  • the numerical values for the amounts of the ingredients shown in Tables 1 and 2 are all based on "% by weight" as active raw materials.
  • the pH of the compositions according to Examples 1-11 and Comparative Examples 1-7 were 8.8.
  • compositions according to Examples 1-11 and Comparative Examples 1-7 were used for permanent waving of the hair.
  • compositions according to Example 1-11 and Comparative Examples 1-7 in an amount of 40 g was applied to the hair on half of the head of each of 4 panelists, the hair was wound around a rod, and the hair was left for 30 min. Then, the hair was rinsed off with water. Next, an oxidizing lotion (neutralizer) which has the composition shown in Table 3 below was applied onto the hair, and the hair was left for 20 min. Then, the rod was removed, and the hair was rinsed off with water and dried.
  • neutralizer neutralizer
  • the panelists evaluated the cosmetic properties, such as wave intensity, deepness, regularity of curl, wave elasticity and suppleness, provided by the compositions according to Examples 1-11 and Comparative Examples 1-7 in accordance with the criteria shown below.
  • Wave intensity the greater the number of curls formed, the stronger the wave intensity is.
  • Deepness defined waves: the shorter the hair length becomes after the permanent waving process, the more deepness it has.
  • Regularity of curl the more each curl size and curl shape from the root to the tip of the hair are similar to each other, the more regularity of curl.
  • Wave elasticity when the wet waved hair is pulled to the same length and then released, the longer the bounce lasts, the more wave elasticity.
  • compositions according to Comparative Examples 1-6 do not comprise a polyol with 4 or more carbon atoms in an amount of less than 1.0% by weight relative to the total weight of the composition, and therefore, the cosmetic properties provided by the compositions according to Comparative Examples 1-6 are inferior to those provided by the compositions according to Examples 1-9.
  • composition according to Example 1 includes a combination of ethanolamine thioglycolate and cysteine (ingredients (a)), and 0.1% by weight of pentyleneglycol
  • composition according to Example 1 can provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 1 including 2.5% by weight of pentyleneglcol or Comparative Example 6, as a control, including no polyol.
  • composition according to Example 2 includes a combination of ethanolamine
  • composition according to Example 2 can also provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 6.
  • composition according to Example 3 includes a combination of ethanolamine
  • composition according to Example 3 can provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 2 including 2.5% by weight of hexyelne glycol or Comparative Example 6, as a control, including no polyol.
  • composition according to Example 4 includes a combination of ethanolamine
  • composition according to Example 4 can also provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 6.
  • composition according to Example 5 includes a combination of ethanolamine
  • composition according to Example 5 can provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 3 including 2.5% by weight of butyleneglycol or Comparative Example 6, as a control, including no polyol.
  • composition according to Example 6 includes a combination of ethanolamine
  • composition according to Example 6 can also provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 6.
  • composition according to Example 7 includes a combination of ethanolamine
  • composition according to Example 7 can provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 1 including 2.5% by weight of pentyleneglcol or Comparative Example 6, as a control, including no polyol. These cosmetic effects provided by Example 7 are inferior to those provided by Example 1.
  • Example 7 the cosmetic effects provided by Example 7 are sufficient to realize the purpose of the present invention.
  • composition according to Example 8 includes a combination of ethanolamine
  • composition according to Example 8 can provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 2 including 2.5% by weight of hexyelne glycol or
  • Comparative Example 6 as a control, including no polyol. These cosmetic effects provided by Example 8 are inferior to those provided by Example 2. However, the cosmetic effects provided by Example 8 are sufficient to realize the purpose of the present invention.
  • the composition according to Example 9 includes a combination of ethanolamine
  • composition according to Example 9 can provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 3 including 2.5% by weight of butyleneglycol or Comparative Example 6, as a control, including no polyol.
  • These cosmetic effects provided by Example 9 are inferior to those provided by Example 3.
  • the cosmetic effects provided by Example 9 are sufficient to realize the purpose of the present invention.
  • composition according to Comparative Example 4 including 0.1% by weight of propylene cannot exert better cosmetic effects than Comparative Example 6 which is a control including no polyol. Rather, the composition according to Comparative Example 5 including 2.5% by weight of propylene exert inferior cosmetic effects to Comparative
  • Example 6 which is a control including no polyol. It should be noted that the addition of a relatively large amount of polyol does not contribute to enhance cosmetic effects.
  • the composition according to Comparative Example 7 does not comprise a polyol with 4 or more carbon atoms in an amount of less than 1.0% by weight relative to the total weight of the composition, and therefore, the cosmetic properties provided by the composition according to Comparative Example 7 are inferior to those provided by the compositions according to Examples 10 and 11.
  • the composition according to Example 10 includes a combination of cysteamine HC1 and ammonium thioglycolate (ingredients (a)), and 0.1% by weight of pentyleneglycol (ingredient (b)).
  • the composition according to Example 10 can provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 7 including no pentyleneglcol.
  • the composition according to Example 11 includes a combination of cysteamine HC1 and ammonium thioglycolate (ingredients (a)), and 0.1% by weight of hexyleneglycol (ingredient (b)).
  • the composition according to Example 11 can provide hair with stronger wave intensity, deeper curls, better regularity of curls, better wave elasticity and better suppleness of the hair than Comparative Example 7 including no hexyleneglycol.
  • the evaluation results for Examples 1-11 show that the use of a combination of a reducing agent and a polyol with 4 or more carbon atoms in an amount of less than 1.0% by weight relative to the total weight of the composition can provide superior cosmetic effects such as good wave intensity, good deepness, good regularity of curl, good wave elasticity and good suppleness.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne une composition pour fibres de kératine, telles que les cheveux, comprenant : (a) au moins un agent de réduction; (b) au moins un polyol avec au moins 4 atomes de carbone, la quantité du polyol dans la composition étant inférieure à 1,0 % en poids par rapport au poids total de la composition. La présente invention peut être utilisée pour déformer ou remettre en forme des fibres de kératine, de préférence des cheveux, et peut fournir aux fibres de kératine une efficacité de remise en forme suffisante, telle qu'une intensité d'onde puissante, une profondeur d'onde distincte et une bonne régularité de boucle, ainsi qu'une lésion moins importante des fibres de kératine, ce qui permet d'obtenir d'excellents effets de conditionnement de cheveux, tels qu'une bonne élasticité et souplesse des fibres de kératine.
PCT/JP2016/072243 2015-07-28 2016-07-22 Composition, processus, procédé et utilisation destinés à des fibres de kératine Ceased WO2017018498A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2015148518A JP2017025051A (ja) 2015-07-28 2015-07-28 ケラチン繊維用の組成物、プロセス、方法及び使用
JP2015-148518 2015-07-28

Publications (1)

Publication Number Publication Date
WO2017018498A1 true WO2017018498A1 (fr) 2017-02-02

Family

ID=56738153

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2016/072243 Ceased WO2017018498A1 (fr) 2015-07-28 2016-07-22 Composition, processus, procédé et utilisation destinés à des fibres de kératine

Country Status (2)

Country Link
JP (1) JP2017025051A (fr)
WO (1) WO2017018498A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019074128A1 (fr) * 2017-10-12 2019-04-18 L'oreal Procédé de remodelage de fibres de kératine

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7353754B2 (ja) * 2018-12-14 2023-10-02 ロレアル ケラチン繊維の矯正法

Citations (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2261002A (en) 1941-06-17 1941-10-28 Du Pont Organic nitrogen compounds
US2271378A (en) 1939-08-30 1942-01-27 Du Pont Pest control
US2273780A (en) 1939-12-30 1942-02-17 Du Pont Wax acryalte ester blends
US2375853A (en) 1942-10-07 1945-05-15 Du Pont Diamine derivatives
US2388614A (en) 1942-05-05 1945-11-06 Du Pont Disinfectant compositions
US2454547A (en) 1946-10-15 1948-11-23 Rohm & Haas Polymeric quaternary ammonium salts
US3206462A (en) 1962-10-31 1965-09-14 Dow Chemical Co Quaternary poly(oxyalkylene)alkylbis(diethylenetriamine) compounds
FR1492597A (fr) 1965-09-14 1967-08-18 Union Carbide Corp Nouveaux éthers cellulosiques contenant de l'azote quaternaire
US3589578A (en) 1968-01-20 1971-06-29 Monforts Fa A Tension-relieving device for stretchable sheet material
FR2077143A5 (fr) 1970-01-30 1971-10-15 Gaf Corp
FR2080759A1 (fr) 1970-02-25 1971-11-19 Gillette Co
FR2162025A1 (fr) 1971-11-29 1973-07-13 Oreal
FR2190406A2 (fr) 1972-06-29 1974-02-01 Gillette Co
US3874870A (en) 1973-12-18 1975-04-01 Mill Master Onyx Corp Microbiocidal polymeric quarternary ammonium compounds
FR2252840A1 (fr) 1973-11-30 1975-06-27 Oreal
FR2270846A1 (fr) 1974-05-16 1975-12-12 Oreal
US3929990A (en) 1973-12-18 1975-12-30 Millmaster Onyx Corp Microbiocidal polymeric quaternary ammonium compounds
FR2280361A2 (fr) 1974-08-02 1976-02-27 Oreal Compositions de traitement et de conditionnement de la chevelure
US3966904A (en) 1974-10-03 1976-06-29 Millmaster Onyx Corporation Quaternary ammonium co-polymers for controlling the proliferation of bacteria
US4001432A (en) 1974-10-29 1977-01-04 Millmaster Onyx Corporation Method of inhibiting the growth of bacteria by the application thereto of capped polymers
US4005193A (en) 1974-08-07 1977-01-25 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
FR2316271A1 (fr) 1975-07-04 1977-01-28 Oreal Nouveaux polymeres quaternises, leur procede de preparation, et leur application
FR2320330A1 (fr) 1974-01-25 1977-03-04 Calgon Corp Composition de polymeres ionenes fonctionnels et leur utilisation
US4025653A (en) 1975-04-07 1977-05-24 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
US4025627A (en) 1973-12-18 1977-05-24 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
US4025617A (en) 1974-10-03 1977-05-24 Millmaster Onyx Corporation Anti-microbial quaternary ammonium co-polymers
US4026945A (en) 1974-10-03 1977-05-31 Millmaster Onyx Corporation Anti-microbial quaternary ammonium co-polymers
US4027020A (en) 1974-10-29 1977-05-31 Millmaster Onyx Corporation Randomly terminated capped polymers
US4031307A (en) 1976-05-03 1977-06-21 Celanese Corporation Cationic polygalactomannan compositions
FR2336434A1 (fr) 1975-12-23 1977-07-22 Ciba Geigy Ag Sels d'ammonium quaternaire polymeres, leur procede de preparation et leur utilisation
FR2368508A2 (fr) 1977-03-02 1978-05-19 Oreal Composition de conditionnement de la chevelure
FR2383660A1 (fr) 1977-03-15 1978-10-13 Oreal Composition et procede de traitement de matieres keratiniques avec des polymeres cationiques et anioniques
US4131576A (en) 1977-12-15 1978-12-26 National Starch And Chemical Corporation Process for the preparation of graft copolymers of a water soluble monomer and polysaccharide employing a two-phase reaction system
FR2393573A1 (fr) 1977-06-10 1979-01-05 Gaf Corp Preparations capillaires contenant un copolymere de vinylpyrrolidone
US4137180A (en) 1976-07-02 1979-01-30 Lever Brothers Company Fabric treatment materials
FR2413907A1 (fr) 1977-09-20 1979-08-03 Oreal Compositions cosmetiques a base de polymeres polyammonium quaternaires
FR2470596A1 (fr) 1979-11-28 1981-06-12 Oreal Composition destinee au traitement des fibres keratiniques a base de polymeres amphoteres et de polymeres cationiques
FR2505348A1 (fr) 1981-05-08 1982-11-12 Oreal Composition sous forme de mousse aerosol a base de polymere cationique et de polymere anionique
EP0080976A1 (fr) 1981-11-30 1983-06-08 Ciba-Geigy Ag Mélanges des sels polymères acryliques d'ammonium quaternaire, de sels mono- ou oligomères d'ammonium quaternaire et de tensioactifs, leur préparation et leur utilisation dans des compositions cosmétiques
FR2519863A1 (fr) 1982-01-15 1983-07-22 Oreal Composition cosmetique destinee au traitement des fibres keratiniques et procede de traitement de celles-ci
US4459284A (en) 1980-07-10 1984-07-10 Nikko Pharmaceutical Co., Ltd. Permanent waving composition comprising amino acids
FR2542997A1 (fr) 1983-03-23 1984-09-28 Oreal Composition epaissie ou gelifiee de conditionnement des cheveux contenant au moins un polymere cationique, au moins un polymere anionique et au moins une gomme de xanthane
FR2598611A1 (fr) 1986-05-16 1987-11-20 Oreal Compositions cosmetiques renfermant un polymere cationique et un polymere anionique comme agent epaississant
US4874554A (en) 1986-07-10 1989-10-17 Henkel Kommanditgesellschaft Auf Aktien Quaternary ammonium compounds
EP0337354A1 (fr) 1988-04-12 1989-10-18 Kao Corporation Composition détergente faiblement irritante
EP0354835A1 (fr) 1988-08-04 1990-02-14 L'oreal N-(mercaptoalkyl)oméga-hydroxyalkylamides et leur utilisation en tant qu'agents réducteurs dans un procédé de déformation permanente des cheveux
EP0368763A1 (fr) 1988-11-09 1990-05-16 L'oreal Mercapto-4 butyramides N-mono ou N,N-disubstitués par un radical mono ou polyhydroxyalkyle, et leur utilisation en tant qu'agents réducteurs dans un procédé de déformation permanente des cheveux
EP0432000A1 (fr) 1989-11-20 1991-06-12 L'oreal Composition rÀ©ductrice, pour déformation permanente des cheveux, contenant en tant qu'agent réducteur un amino mercaptoalkylamide ou l'un de ses sels, et son utilisation dans un procédé de déformation permanente des cheveux
EP0514282A1 (fr) 1991-05-17 1992-11-19 L'oreal Nouveaux alkylamino mercaptoalkylamides ou l'un de leurs sels cosmétiquement acceptables, et leur utilisation en tant qu'agents réducteurs, dans un procédé de déformation permanente des cheveux
FR2679448A1 (fr) 1991-07-23 1993-01-29 Oreal Melange azetrope de thioglycolate d'hydroxy-2 propyle et de thioglycolate d'hydroxy-2 methyl-1 ethyle, son procede d'obtention et son utilisation dans un procede de deformation permanente des cheveux.
US5364633A (en) 1994-03-14 1994-11-15 Dow Corning Corporation Silicone vesicles and entrapment
EP1155678A1 (fr) * 2000-05-18 2001-11-21 GOLDWELL GmbH Composition pour la déformation permanente des cheveux
FR2814948A1 (fr) 2000-10-11 2002-04-12 Oreal Composition cosmetique contenant des derives d'acide sulfinique
FR2870119A1 (fr) 2004-05-17 2005-11-18 Oreal Utilisation pour le decapage de la couleur artificielle des fibres keratiniques d'une composition comprenant au moins une phosphine a titre d'agent reducteur majoritaire
EP1880710A1 (fr) * 2006-07-21 2008-01-23 Wella Aktiengesellschaft Méthode et agent pour la déformation permanente de cheveux

Patent Citations (57)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2271378A (en) 1939-08-30 1942-01-27 Du Pont Pest control
US2273780A (en) 1939-12-30 1942-02-17 Du Pont Wax acryalte ester blends
US2261002A (en) 1941-06-17 1941-10-28 Du Pont Organic nitrogen compounds
US2388614A (en) 1942-05-05 1945-11-06 Du Pont Disinfectant compositions
US2375853A (en) 1942-10-07 1945-05-15 Du Pont Diamine derivatives
US2454547A (en) 1946-10-15 1948-11-23 Rohm & Haas Polymeric quaternary ammonium salts
US3206462A (en) 1962-10-31 1965-09-14 Dow Chemical Co Quaternary poly(oxyalkylene)alkylbis(diethylenetriamine) compounds
FR1492597A (fr) 1965-09-14 1967-08-18 Union Carbide Corp Nouveaux éthers cellulosiques contenant de l'azote quaternaire
US3589578A (en) 1968-01-20 1971-06-29 Monforts Fa A Tension-relieving device for stretchable sheet material
FR2077143A5 (fr) 1970-01-30 1971-10-15 Gaf Corp
FR2080759A1 (fr) 1970-02-25 1971-11-19 Gillette Co
FR2162025A1 (fr) 1971-11-29 1973-07-13 Oreal
FR2190406A2 (fr) 1972-06-29 1974-02-01 Gillette Co
FR2252840A1 (fr) 1973-11-30 1975-06-27 Oreal
US3874870A (en) 1973-12-18 1975-04-01 Mill Master Onyx Corp Microbiocidal polymeric quarternary ammonium compounds
US3929990A (en) 1973-12-18 1975-12-30 Millmaster Onyx Corp Microbiocidal polymeric quaternary ammonium compounds
US4025627A (en) 1973-12-18 1977-05-24 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
FR2320330A1 (fr) 1974-01-25 1977-03-04 Calgon Corp Composition de polymeres ionenes fonctionnels et leur utilisation
FR2270846A1 (fr) 1974-05-16 1975-12-12 Oreal
FR2280361A2 (fr) 1974-08-02 1976-02-27 Oreal Compositions de traitement et de conditionnement de la chevelure
US4005193A (en) 1974-08-07 1977-01-25 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
US3966904A (en) 1974-10-03 1976-06-29 Millmaster Onyx Corporation Quaternary ammonium co-polymers for controlling the proliferation of bacteria
US4025617A (en) 1974-10-03 1977-05-24 Millmaster Onyx Corporation Anti-microbial quaternary ammonium co-polymers
US4026945A (en) 1974-10-03 1977-05-31 Millmaster Onyx Corporation Anti-microbial quaternary ammonium co-polymers
US4001432A (en) 1974-10-29 1977-01-04 Millmaster Onyx Corporation Method of inhibiting the growth of bacteria by the application thereto of capped polymers
US4027020A (en) 1974-10-29 1977-05-31 Millmaster Onyx Corporation Randomly terminated capped polymers
US4025653A (en) 1975-04-07 1977-05-24 Millmaster Onyx Corporation Microbiocidal polymeric quaternary ammonium compounds
FR2316271A1 (fr) 1975-07-04 1977-01-28 Oreal Nouveaux polymeres quaternises, leur procede de preparation, et leur application
FR2336434A1 (fr) 1975-12-23 1977-07-22 Ciba Geigy Ag Sels d'ammonium quaternaire polymeres, leur procede de preparation et leur utilisation
US4031307A (en) 1976-05-03 1977-06-21 Celanese Corporation Cationic polygalactomannan compositions
US4137180A (en) 1976-07-02 1979-01-30 Lever Brothers Company Fabric treatment materials
FR2368508A2 (fr) 1977-03-02 1978-05-19 Oreal Composition de conditionnement de la chevelure
FR2383660A1 (fr) 1977-03-15 1978-10-13 Oreal Composition et procede de traitement de matieres keratiniques avec des polymeres cationiques et anioniques
FR2393573A1 (fr) 1977-06-10 1979-01-05 Gaf Corp Preparations capillaires contenant un copolymere de vinylpyrrolidone
FR2413907A1 (fr) 1977-09-20 1979-08-03 Oreal Compositions cosmetiques a base de polymeres polyammonium quaternaires
US4131576A (en) 1977-12-15 1978-12-26 National Starch And Chemical Corporation Process for the preparation of graft copolymers of a water soluble monomer and polysaccharide employing a two-phase reaction system
FR2470596A1 (fr) 1979-11-28 1981-06-12 Oreal Composition destinee au traitement des fibres keratiniques a base de polymeres amphoteres et de polymeres cationiques
US4459284A (en) 1980-07-10 1984-07-10 Nikko Pharmaceutical Co., Ltd. Permanent waving composition comprising amino acids
JPS629566B2 (fr) 1980-07-10 1987-02-28 Tanabe Seiyaku Kk
FR2505348A1 (fr) 1981-05-08 1982-11-12 Oreal Composition sous forme de mousse aerosol a base de polymere cationique et de polymere anionique
EP0080976A1 (fr) 1981-11-30 1983-06-08 Ciba-Geigy Ag Mélanges des sels polymères acryliques d'ammonium quaternaire, de sels mono- ou oligomères d'ammonium quaternaire et de tensioactifs, leur préparation et leur utilisation dans des compositions cosmétiques
FR2519863A1 (fr) 1982-01-15 1983-07-22 Oreal Composition cosmetique destinee au traitement des fibres keratiniques et procede de traitement de celles-ci
FR2542997A1 (fr) 1983-03-23 1984-09-28 Oreal Composition epaissie ou gelifiee de conditionnement des cheveux contenant au moins un polymere cationique, au moins un polymere anionique et au moins une gomme de xanthane
FR2598611A1 (fr) 1986-05-16 1987-11-20 Oreal Compositions cosmetiques renfermant un polymere cationique et un polymere anionique comme agent epaississant
US4874554A (en) 1986-07-10 1989-10-17 Henkel Kommanditgesellschaft Auf Aktien Quaternary ammonium compounds
EP0337354A1 (fr) 1988-04-12 1989-10-18 Kao Corporation Composition détergente faiblement irritante
EP0354835A1 (fr) 1988-08-04 1990-02-14 L'oreal N-(mercaptoalkyl)oméga-hydroxyalkylamides et leur utilisation en tant qu'agents réducteurs dans un procédé de déformation permanente des cheveux
EP0368763A1 (fr) 1988-11-09 1990-05-16 L'oreal Mercapto-4 butyramides N-mono ou N,N-disubstitués par un radical mono ou polyhydroxyalkyle, et leur utilisation en tant qu'agents réducteurs dans un procédé de déformation permanente des cheveux
EP0432000A1 (fr) 1989-11-20 1991-06-12 L'oreal Composition rÀ©ductrice, pour déformation permanente des cheveux, contenant en tant qu'agent réducteur un amino mercaptoalkylamide ou l'un de ses sels, et son utilisation dans un procédé de déformation permanente des cheveux
EP0514282A1 (fr) 1991-05-17 1992-11-19 L'oreal Nouveaux alkylamino mercaptoalkylamides ou l'un de leurs sels cosmétiquement acceptables, et leur utilisation en tant qu'agents réducteurs, dans un procédé de déformation permanente des cheveux
FR2679448A1 (fr) 1991-07-23 1993-01-29 Oreal Melange azetrope de thioglycolate d'hydroxy-2 propyle et de thioglycolate d'hydroxy-2 methyl-1 ethyle, son procede d'obtention et son utilisation dans un procede de deformation permanente des cheveux.
US5364633A (en) 1994-03-14 1994-11-15 Dow Corning Corporation Silicone vesicles and entrapment
US5411744A (en) 1994-03-14 1995-05-02 Dow Corning Corporation Silicone vesicles and entrapment
EP1155678A1 (fr) * 2000-05-18 2001-11-21 GOLDWELL GmbH Composition pour la déformation permanente des cheveux
FR2814948A1 (fr) 2000-10-11 2002-04-12 Oreal Composition cosmetique contenant des derives d'acide sulfinique
FR2870119A1 (fr) 2004-05-17 2005-11-18 Oreal Utilisation pour le decapage de la couleur artificielle des fibres keratiniques d'une composition comprenant au moins une phosphine a titre d'agent reducteur majoritaire
EP1880710A1 (fr) * 2006-07-21 2008-01-23 Wella Aktiengesellschaft Méthode et agent pour la déformation permanente de cheveux

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
"CTFA dictionary", 1982
"the CTFA dictionary", 1993
"the CTFA International Cosmetic Ingredient Dictionary & Handbook", 2014
M. R. PORTER: "Handbook of Surfactants", 1991, BLACKIE & SON PUBLISHERS, pages: 116 - 178

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019074128A1 (fr) * 2017-10-12 2019-04-18 L'oreal Procédé de remodelage de fibres de kératine
KR20200060495A (ko) * 2017-10-12 2020-05-29 로레알 케라틴 섬유를 재성형하기 위한 방법
CN111328277A (zh) * 2017-10-12 2020-06-23 莱雅公司 用于使角蛋白纤维再成型的方法
KR102410107B1 (ko) * 2017-10-12 2022-06-16 로레알 케라틴 섬유를 재성형하기 위한 방법
US11413230B2 (en) 2017-10-12 2022-08-16 L'oreal Process for reshaping keratin fibers

Also Published As

Publication number Publication date
JP2017025051A (ja) 2017-02-02

Similar Documents

Publication Publication Date Title
JP6914837B2 (ja) ケラチン繊維を処置するための方法
EP3694475B1 (fr) Procede de recoiffage des fibres keratiniques
WO2013092779A2 (fr) Composition cosmétique comprenant au moins une silicone fonctionnalisée avec un ou plusieurs groupes mercapto et au moins un sel hygroscopique
WO2017041905A1 (fr) Procédé de mise en forme permanente des cheveux
EP3694478B1 (fr) Procede de recoiffage des fibres keratiniques
WO2018058205A1 (fr) Compositions cosmétiques capillaires contenant des composés à base de thiol et procédés de nettoyage et de traitement des cheveux
KR20210013015A (ko) 환원제를 포함하는 모발 트리트먼트 조성물
JP6257535B2 (ja) ケラチン繊維のための化粧用組成物
EP3528775A1 (fr) Procédé de traitement capillaire
WO2017018498A1 (fr) Composition, processus, procédé et utilisation destinés à des fibres de kératine
WO2016076437A1 (fr) Composition pour fibres de kératine
EP3463276B1 (fr) Procédé pour traiter les cheveux
JP6317060B2 (ja) ケラチン繊維を処理する方法
JP2016113435A (ja) ケラチン繊維を処置するための方法
JP2016113436A (ja) ケラチン繊維を処置するための方法
JP6973983B2 (ja) ケラチン繊維用の組成物、プロセス、方法及び使用
WO2019197852A1 (fr) Compositions de traitement capillaire comprenant des agents réducteurs
EP4076357A1 (fr) Procédé de traitement cosmétique de fibres kératiniques à l'aide d'un métal des terres rares et d'un polymère particulier
WO2016120656A1 (fr) Composition comprenant une aminosilicone, un polymère de phospholipide, et un polymère associatif cationique

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 16753719

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16753719

Country of ref document: EP

Kind code of ref document: A1