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WO2025043531A1 - Composition colorante pour colorer des fibres de kératine et kit la comprenant - Google Patents

Composition colorante pour colorer des fibres de kératine et kit la comprenant Download PDF

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Publication number
WO2025043531A1
WO2025043531A1 PCT/CN2023/115757 CN2023115757W WO2025043531A1 WO 2025043531 A1 WO2025043531 A1 WO 2025043531A1 CN 2023115757 W CN2023115757 W CN 2023115757W WO 2025043531 A1 WO2025043531 A1 WO 2025043531A1
Authority
WO
WIPO (PCT)
Prior art keywords
colorant composition
diamino
mixtures
keratin fibers
carbon atoms
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.)
Pending
Application number
PCT/CN2023/115757
Other languages
English (en)
Inventor
Yanan WU
Zhibing Liu
Jingmiao MA
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
Priority to PCT/CN2023/115757 priority Critical patent/WO2025043531A1/fr
Priority to FR2310921A priority patent/FR3152390B3/fr
Publication of WO2025043531A1 publication Critical patent/WO2025043531A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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
    • A61Q5/10—Preparations for permanently dyeing 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers

Definitions

  • the present invention relates to a cosmetic composition.
  • the present invention relates to a colorant composition for dyeing keratin fibers and a kit comprising the same.
  • the present invention also relates to a process for dyeing keratin fibers.
  • the dyeing product can comprise both at least one oxidative dye and at least one oxidant.
  • the oxidative dye and the oxidant may be placed respectively in a multi-compartment package, and be mixed together immediately before use.
  • hair colorant products are stable.
  • One aim of the present application is to provide a colorant composition for dyeing the hair comprising 4, 5-diamino-1- ( ⁇ -hydroxyethyl) pyrazole or the like, which is stable and preferably is in the form of liquid cream so as to be easily applied.
  • Another aim of the present application is to provide a process for dyeing the hair.
  • the present invention provides a colorant composition for dyeing keratin fibers, comprising:
  • At least one oxidative base selected from aminopyrazoles, their addition salts, and mixtures thereof;
  • hydrophilic gelling polymer selected from anionic acrylic copolymers.
  • the colorant composition for dyeing keratin fibers according to the present invention is stable and in some embodiments is in the form of liquid cream and can be easily applied.
  • the colorant composition according to the present invention can be used to dye keratin fibers in combination with a developer composition.
  • the present invention provides a kit for dyeing keratin fibers, comprising:
  • the present invention provides a process for dyeing keratin fibers, comprising:
  • the present invention provides a use of a polysaccharide of ⁇ -Carrageenan type for improving the stability of a colorant composition
  • a polysaccharide of ⁇ -Carrageenan type for improving the stability of a colorant composition
  • a colorant composition comprising at least one oxidative base selected from aminopyrazoles, their addition salts, and mixtures thereof.
  • keratin fibers includes animal keratin fibers and human keratin fibers such as the hair.
  • the colorant composition according to the present invention comprises:
  • At least one oxidative base selected from aminopyrazoles, their addition salts, and mixtures thereof;
  • hydrophilic gelling polymer selected from anionic acrylic copolymers.
  • the colorant composition of the present invention comprises at least one oxidative base selected from aminopyrazoles and its addition salts.
  • aminopyrazoles mention can be made of4, 5-diamino-1-methylpyrazole, 4, 5-diamino-1- ( ⁇ -hydroxyethyl) pyrazole, 3, 4-diaminopyrazole, 4, 5-diamino-1- (4'-chlorobenzyl) pyrazole, 4, 5-diamino-1, 3-dimethylpyrazole, 4, 5-diamino-3-methyl-1-phenylpyrazole, 4, 5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1, 3-dimethyl-5-hydrazinopyrazole, 1-benzyl-4, 5-diamino-3-methylpyrazole, 4, 5-diamino-3-tert-butyl-1-methylpyrazole, 4, 5-diamino-1-tert-butyl-3-methylpyrazole, 4, 5-diamino-1- (2-hydroxyethyl) -3-methylpyrazole, 4, 5-diamino
  • the oxidative base is selected from 4, 5-diamino-1-methylpyrazole, 4, 5-diamino-1- ( ⁇ -hydroxyethyl) pyrazole, 3, 4-diaminopyrazole, 4, 5-diamino-1- (4'-chlorobenzyl) pyrazole, 4, 5-diamino-1, 3-dimethylpyrazole, 4, 5-diamino-3-methyl-1-phenylpyrazole, 4, 5-diamino-1-methyl-3-phenylpyrazole, 1-benzyl-4, 5-diamino-3-methylpyrazole, 4, 5-diamino-3-tert-butyl-1-methylpyrazole, 4, 5-diamino-1-tert-butyl-3-methylpyrazole, 4, 5-diamino-1- (2-hydroxyethyl) -3-methylpyrazole, 4, 5-diamino-1-ethyl-3-methylpyrazole, 4, 5-diamino-1-( ⁇
  • the oxidative base is selected from 4, 5-diamino-1- ( ⁇ -hydroxyethyl) pyrazole (also named 1-hydroxyethyl-4, 5-diamino pyrazole) , its sulphates, chlorides, dimethosulfonates, and mixtures thereof.
  • the oxidative base is present in the colorant composition of the present invention in an amount ranging from 0.5 wt. %to 8 wt. %, or from 0.6 wt. %to 6 wt. %, or from 0.7 wt. %to 7 wt. %, preferably from 0.8 wt. %to 6 wt. %, or from 1 wt. %to 5 wt. %, or from 1.1 wt. %to 4 wt. %, and more preferably or from 1.2 wt. %to 3 wt. %, or from 1.2 wt. %to 2.5 wt. %, relative to the total weight of the colorant composition.
  • the polysaccharide of ⁇ -carrageenan is not chemically modified.
  • the molecular weight (M W ) of the polysaccharide of ⁇ -carrageenan ranges from 100,000 to 1,000,000. More preferably, the molecular weight (M W ) of the ⁇ -carrageenan ranges from 250,000 to 800,000.
  • %to 1.4 wt. % and more preferably from 0.15 wt. %to 1.2 wt. %, or from 0.2 wt. %to 1 wt. %, relative to the total weight of the colorant composition.
  • the colorant composition of the present invention comprises at least one hydrophilic gelling polymer selected from anionic acrylic copolymers.
  • the term "hydrophilic gelling polymer” means a polymer that is capable of thickening an aqueous medium.
  • the thickening polymer has, at 1%in water or in a 50/50 water/alcohol mixture by weight at 25°C, absorbcosity of greater than 100 centipoise at a shear rate of 1 s -1 .
  • the viscosity can be measured using in particular viscometers or rheometers having cone-plate geometry.
  • acrylic copolymer means a polymer resulting from the copolymerization of at least two chemically different monomers, at least one of which is selected from unsaturated carboxylic acids, preferably acrylic acid or methacrylic acid.
  • anionic copolymers derived from at least one unsaturated carboxylic acid and at least one ester of an unsaturated carboxylic acid and of a monoalcohol comprising from 1 to 6 carbon atoms and preferably from 1 to 4 carbon atoms;
  • hydrophobic group means a group or a polymer bearing a saturated or unsaturated and linear or branched hydrocarbon-based chain.
  • the hydrophobic group comprises at least 8 carbon atoms, preferably from 10 to 30 carbon atoms, in particular from 12 to 30 carbon atoms, from 12 to 24 carbon atoms and preferentially from 16 to 22 carbon atoms.
  • the hydrocarbon-based hydrophobic group originates from a monofunctional compound.
  • the unsaturated carboxylic acid which is in particular ⁇ , ⁇ -monoethylenically unsaturated, is a monomer corresponding to formula (I) below:
  • R 1 denotes H or CH 3 or C 2 H 5 (i.e. acrylate, methacrylate or ethacrylate units) and preferably H (acrylate units) or CH 3 (methacrylate units)
  • R 2 denotes an alkyl group comprising from 1 to 6 carbon atoms and preferably from 1 to 4 carbon atoms.
  • esters of an unsaturated carboxylic acid and of a fatty monoalcohol comprising from 1 to 6 carbon atoms according to formula (II) mention may be made more particularly of methyl acrylate, ethyl acrylate, propyl acrylate and butyl acrylate, and the corresponding methacrylates, methyl methacrylate, ethyl methacrylate, propyl methacrylate and butyl methacrylate.
  • anionic copolymers of this type use will more particularly be made of the polymers constituted of the following monomers:
  • R 1 denotes H or CH 3 or C 2 H 5 , which corresponds to acrylic acid, methacrylic acid or ethacrylic acid units;
  • R 1 denotes H or CH 3 or C 2 H 5 (i.e. acrylate, methacrylate or ethacrylate units) and preferably H (acrylate units) or CH 3 (methacrylate units)
  • R 2 denotes an alkyl group comprising from 1 to 6 carbon atoms and preferably from 1 to 4 carbon atoms
  • crosslinking agent which is a well-known copolymerizable polyethylenic unsaturated monomer, such as diallyl phthalate, allyl (meth) acrylate, divinylbenzene, (poly) ethylene glycol dimethacrylate or methylenebisacrylamide.
  • anionic copolymers as defined above are the crosslinked copolymer of acrylic acid and of ethyl acrylate sold under the trade name Aculyn 33 by the company Rohm&Haas, which is in aqueous dispersion containing 28%by weight of active material, the methacrylic acid/ethyl acrylate crosslinked copolymer in the form of an aqueous dispersion at 30%by weight (INCI name: Acrylates Copolymer) sold under the name Carbopol Aqua SF-1 Polymer by the company Lubrizol, and the copolymer of (meth) acrylic acid and of a C 1 -C 4 alkyl (meth) acrylate sold under the name Synthalen W400 by the company 3V Sigma, at 30%by weight of active material in water.
  • these anionic copolymers are selected from crosslinked copolymers of (meth) acrylic acid and of a C 1 -C 4 alkyl (meth) acrylate, and better still from crosslinked copolymers of (meth) acrylic acid and of ethyl (meth) acrylate.
  • anionic associative acrylic copolymers that may be used in the context of the invention, mention may be made of:
  • R denotes H or CH 3
  • B denotes the ethyleneoxy group (-CH 2 -CH 2 -O-)
  • n is zero or denotes an integer ranging from 1 to 100 (especially from 5 to 15)
  • R denotes a hydrocarbon-based group selected from alkyl, arylalkyl, aryl, alkylaryl and cycloalkyl groups comprising from 8 to 30 carbon atoms, preferably from 10 to 24 carbon atoms and even more particularly from 16 to 20 carbon atoms.
  • a monomer of formula (III) that is more particularly preferred is a monomer in which R' denotes H, n is equal to 10 and R denotes a stearyl (C18) group.
  • anionic associative acrylic copolymers the ones that are particularly preferred are polymers formed from 20%to 60%by weight of (meth) acrylic acid, from 5%to 60%by weight of C 1 -C 4 alkyl (meth) acrylate, from 2%to 50%by weight of monomer of formula (III) , and from 0 to 1%by weight of a crosslinking agent which is a well-known copolymerizable unsaturated polyethylenic monomer, for instance diallyl phthalate, allyl (meth) acrylate, divinylbenzene, (poly) ethylene glycol dimethacrylate or methylenebisacrylamide.
  • a crosslinking agent which is a well-known copolymerizable unsaturated polyethylenic monomer, for instance diallyl phthalate, allyl (meth) acrylate, divinylbenzene, (poly) ethylene glycol dimethacrylate or methylenebisacrylamide.
  • associative polymers comprising at least one hydrophilic unit of unsaturated ethylenic carboxylic acid type and at least one hydrophobic unit of (C 10 -C 30 ) alkyl ester of unsaturated carboxylic acid type.
  • these polymers are selected from copolymers of (i) a monomer of formula (IV) below:
  • R 1 denotes H or CH 3 or C 2 H 5
  • (ii) monomer of the following formula (V) (monomer of (C 10 -C 30 ) alkyl ester of unsaturated carboxylic acid type) : H 2 C CR 1 -COOR 3 (V)
  • R 1 denotes H or CH 3 or C 2 H 5 and preferably H or CH 3
  • R 3 denotes a C 10 -C 30 and preferably C 12 -C 22 alkyl group.
  • the monomer (IV) constitutes the hydrophilic unit and the monomer (V) constitutes the hydrophobic unit.
  • (C 10 -C 30 ) alkyl esters of unsaturated carboxylic acids comprise, for example, lauryl (meth) acrylate, stearyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate and dodecyl (meth) acrylate.
  • anionic associative polymers of this type that will be used more particularly are polymers formed from a monomer mixture comprising:
  • crosslinking agent which is a well-known copolymerizable polyethylenic unsaturated monomer, such as diallyl phthalate, allyl (meth) acrylate, divinylbenzene, (poly) ethylene glycol dimethacrylate or methylenebisacrylamide.
  • anionic associative polymers of this type use will be made more particularly of:
  • Pemulen TR1 and Carbopol 1382 are the products sold by the company Lubrizol under the trade names Pemulen TR1, Pemulen TR2, Carbopol 1382, Carbopol ETD 2020, Carbopol Ultrez 20 and Carbopol Ultrez 21 (INCI name: Acrylates/C 10-30 alkyl acrylate crosspolymer) , and even more preferentially Pemulen TR1 and Carbopol 1382;
  • acrylic terpolymers comprising:
  • R2 is selected from linear alkyl radicals comprising from 18 to 26 and preferably from 20 to 24 carbon atoms.
  • R2 is a behenyl radical.
  • the ⁇ , ⁇ -monoethylenically unsaturated carboxylic acid (a) may be selected from acrylic acid, methacrylic acid and crotonic acid. It is preferably (meth) acrylic acid. Preferentially, the monomer (a) is methacrylic acid.
  • the terpolymer contains a monomer (b) selected from C 1 -C 4 alkyl (meth) acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate or butyl (meth) acrylate.
  • the monomer (b) is preferably selected from methyl acrylate and ethyl acrylate.
  • Such terpolymers are generally in the form of an aqueous dispersion.
  • Use is preferentially made of a terpolymer of methacrylic acid/methyl acrylate/condensate of dimethyl m-isopropenyl benzyl isocyanate and of polyoxyethylenated (40 OE) behenyl alcohol (INCI name: Polyacrylate-3) , such as the product sold in the form of an aqueous dispersion at 25%by weight, under the name Viscophobe DB 1000 by the company The Dow Chemical Company;
  • Viscosity was measured by a Mettler RM 180 Rheomat with spindle#3 at 25°C to check if the viscosity of each colorant composition is within a range of 600-1500 mPa. s.
  • composition was prepared and aged for 24 hours at room temperature, then contained in a cosmetic bottle, then put into an over or a refrigerator for storage for a period of time:
  • compositions according to the present invention are stable and can be easily applied.

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

Abstract

L'invention concerne une composition colorante pour colorer des fibres de kératine et un kit la comprenant. La composition colorante comprend i) au moins une base oxydative choisie parmi les aminopyrazoles, leurs sels d'addition et leurs mélanges ; ii) au moins un polysaccharide de type λ-carraghénane ; et iii) au moins un polymère gélifiant hydrophile choisi parmi les copolymères acryliques anioniques. L'invention concerne également un procédé de coloration de fibres de kératine.
PCT/CN2023/115757 2023-08-30 2023-08-30 Composition colorante pour colorer des fibres de kératine et kit la comprenant Pending WO2025043531A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/CN2023/115757 WO2025043531A1 (fr) 2023-08-30 2023-08-30 Composition colorante pour colorer des fibres de kératine et kit la comprenant
FR2310921A FR3152390B3 (fr) 2023-08-30 2023-10-12 Composition de colorant pour la teinture des fibres kératineuses et nécessaire comprenant celle-ci

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2023/115757 WO2025043531A1 (fr) 2023-08-30 2023-08-30 Composition colorante pour colorer des fibres de kératine et kit la comprenant

Publications (1)

Publication Number Publication Date
WO2025043531A1 true WO2025043531A1 (fr) 2025-03-06

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Family Applications (1)

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FR (1) FR3152390B3 (fr)
WO (1) WO2025043531A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2807649A1 (fr) * 2000-04-12 2001-10-19 Oreal Composition pour la teinture d'oxydation des fibres keratiniques comprenant un derive de la 3,5-diamino- pyridine et un polymere epaississant particulier
WO2003075872A1 (fr) * 2002-03-04 2003-09-18 The Procter & Gamble Company Compositions de coloration de cheveux a base de composes de diaminopyrazole
US20060265818A1 (en) * 2003-11-21 2006-11-30 Martina Seiler Method for dyeing fibers containing keratin
WO2013058816A1 (fr) * 2011-02-22 2013-04-25 The Procter & Gamble Company Compositions de coloration oxydative comprenant un 1-hexyl/heptyl-4,5-diaminopyrazole et un 2-aminophénol et des dérivés de ceux-ci
WO2016069865A1 (fr) * 2014-10-29 2016-05-06 The Procter & Gamble Company Procédé et kit de coloration des cheveux
JP2018095858A (ja) * 2016-12-08 2018-06-21 三栄源エフ・エフ・アイ株式会社 増粘剤、増粘組成物、ゲル化剤及びゲル化組成物

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH606154A5 (fr) 1974-07-02 1978-11-15 Goodrich Co B F
US4509949A (en) 1983-06-13 1985-04-09 The B. F. Goodrich Company Water thickening agents consisting of copolymers of crosslinked acrylic acids and esters
US4514552A (en) 1984-08-23 1985-04-30 Desoto, Inc. Alkali soluble latex thickeners
FR2586913B1 (fr) 1985-09-10 1990-08-03 Oreal Procede pour former in situ une composition constituee de deux parties conditionnees separement et ensemble distributeur pour la mise en oeuvre de ce procede

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2807649A1 (fr) * 2000-04-12 2001-10-19 Oreal Composition pour la teinture d'oxydation des fibres keratiniques comprenant un derive de la 3,5-diamino- pyridine et un polymere epaississant particulier
WO2003075872A1 (fr) * 2002-03-04 2003-09-18 The Procter & Gamble Company Compositions de coloration de cheveux a base de composes de diaminopyrazole
US20060265818A1 (en) * 2003-11-21 2006-11-30 Martina Seiler Method for dyeing fibers containing keratin
WO2013058816A1 (fr) * 2011-02-22 2013-04-25 The Procter & Gamble Company Compositions de coloration oxydative comprenant un 1-hexyl/heptyl-4,5-diaminopyrazole et un 2-aminophénol et des dérivés de ceux-ci
WO2016069865A1 (fr) * 2014-10-29 2016-05-06 The Procter & Gamble Company Procédé et kit de coloration des cheveux
JP2018095858A (ja) * 2016-12-08 2018-06-21 三栄源エフ・エフ・アイ株式会社 増粘剤、増粘組成物、ゲル化剤及びゲル化組成物

Also Published As

Publication number Publication date
FR3152390B3 (fr) 2025-10-17
FR3152390A3 (fr) 2025-03-07

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