WO2012084473A1 - Procédé de coloration de fibres kératiniques utilisant des dérivés du résorcinol, des sels de sulfate, un agent oxydant et un agent basifiant - Google Patents

Procédé de coloration de fibres kératiniques utilisant des dérivés du résorcinol, des sels de sulfate, un agent oxydant et un agent basifiant Download PDF

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WO2012084473A1
WO2012084473A1 PCT/EP2011/071744 EP2011071744W WO2012084473A1 WO 2012084473 A1 WO2012084473 A1 WO 2012084473A1 EP 2011071744 W EP2011071744 W EP 2011071744W WO 2012084473 A1 WO2012084473 A1 WO 2012084473A1
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group
alkyl
preferentially
formula
composition
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PCT/EP2011/071744
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English (en)
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Stéphane SABELLE
Christophe Rondot
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L'oreal
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Priority to CN201180061013.4A priority Critical patent/CN103249392B/zh
Publication of WO2012084473A1 publication Critical patent/WO2012084473A1/fr

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    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/23—Sulfur; Selenium; Tellurium; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • A61K8/315—Halogenated hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • 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
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/415—Aminophenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides

Definitions

  • the invention relates to a process for dyeing keratin fibres, especially the hair, using i) at least one resorcinol derivative, ii) at least one sulfate salt, iii) at least one oxidizing agent and iv) at least one basifying agent.
  • This dyeing process affords better colorations, which are chromatic, strong and fast, without the use of oxidation bases such as para- phenylenediamines and para-aminophenols. It is known practice to obtain "permanent" colorations with dye compositions containing oxidation dye precursors, which are generally known as oxidation bases, such as ortho- or para-phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds.
  • oxidation bases are colourless or weakly coloured compounds, which, when combined with oxidizing products, give rise to coloured compounds via a process of oxidative condensation. It is also known that the shades obtained with these oxidation bases may be varied by combining them with couplers or coloration modifiers, the latter being chosen especially from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as indole compounds which show light-fastness and shampoo-fastness.
  • This oxidation dyeing process consists in applying to the keratin fibres bases or a mixture of bases and couplers with hydrogen peroxide H 2 0 2 or aqueous hydrogen peroxide solution, as oxidizing agent, in leaving it to diffuse, and then in rinsing the fibres.
  • the colorations resulting therefrom are permanent, strong and resistant to external agents, especially to light, bad weather, washing, perspiration and rubbing.
  • 5,6-Dihydroxyindole derivatives are also capable of generating dark shades by "autoxidation", but the resulting colorations are not always satisfactory, especially in terms of chromaticity, power or remanence.
  • R 1 and R 4 which may be identical or different, represent a hydrogen or halogen atom, or a group chosen from:
  • M + representing a cationic counterion such as an alkali metal or alkaline-earth metal, or an ammonium
  • R 5 representing a group (C Cio)alkyl, particularly -C(0)-0-R 5 ;
  • R 8 and R 9 which may be identical or different, representing a hydrogen atom or a group (C Cio)alkyl, particularly -NH 2;
  • oxidizing agent preferably a chemical oxidizing agent
  • ingredients i) to iv) may be applied to the fibres either together or separately;
  • the pH of the composition comprising ingredient(s) iv) is basic, i.e. greater than 7; preferentially between 7.5 and 12; and
  • Another subject of the invention is a cosmetic composition for dyeing keratin fibres, comprising:
  • oxidizing agent preferably a chemical oxidizing agent
  • the pH of the composition is basic, i.e. greater than 7; preferentially between 7.5 and 12; and
  • the composition does not contain para- phenylenediamine.
  • Another subject of the invention relates to a multi-compartment device comprising the ingredients i) to iv) as defined previously.
  • the dye composition and the dyeing process of the invention have the advantage of dyeing human keratin fibres, with powerful or chromatic dyeing results that are resistant to washing, perspiration, sebum and light, and that are more long-lasting, without impairing the said fibres. Furthermore, the colorations obtained using the process give uniform colours from the root to the end of a fibre (little coloration selectivity).
  • the shades obtained after dyeing with the composition or the process of the invention are very strong, in particular at a temperature above room temperature, preferentially at a temperature of between 45 and 80°C.
  • the shades obtained with the composition or the process of the invention are compatible with standard oxidation conditions for lightening the hair.
  • the dyeing result is long-lasting and does not change even after several shampoo washes.
  • the colorations are particularly shampoo-fast.
  • an "a/yr radical represents a fused or non-fused monocyclic or polycyclic group containing from 6 to 22 carbon atoms, and in which at least one ring is aromatic; preferentially, the aryl radical is a phenyl, biphenyl, naphthyl, indenyl, anthracenyl or tetrahydronaphthyl; preferably, the aryl group is a phenyl;
  • a/yr radical or the aryl part of a radical may be substituted with at least one substituent borne by a carbon atom, chosen from:
  • a C1-C16 and preferably C C C 8 alkyl radical optionally substituted with one or more radicals chosen from hydroxyl, C C 2 alkoxy, C 2 -C 4 (poly)hydroxyalkoxy, acylamino, amino substituted with two C C 4 alkyl radicals, which may be identical or different, optionally bearing at least one hydroxyl group, or the two radicals possibly forming, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted 5- to 7-membered and preferably 5- or 6-membered heterocycle optionally comprising another nitrogen or non-nitrogen heteroatom;
  • halogen atom such as chlorine, fluorine or bromine
  • hydroxyl group • a halogen atom such as chlorine, fluorine or bromine; a hydroxyl group;
  • a 5- or 6-membered heterocycloalkyl radical such as cyclohexyl
  • an optionally cationic 5- or 6-membered heteroaryl radical preferentially imidazolium, optionally substituted with a (C C 4 )alkyl radical, preferentially methyl;
  • alkyl radicals possibly forming with the nitrogen atom to which they are attached a saturated or unsaturated, optionally substituted 5- to 7- membered heterocycle, optionally comprising at least one other nitrogen or non- nitrogen heteroatom;
  • radical R is a hydrogen atom or a (C C 4 )alkyl radical optionally bearing at least one hydroxyl group and the radical R' is a (CrC 2 )alkyl radical;
  • R 2 N-C(0)- in which the radicals R, which may be identical or different, represent a hydrogen atom or a (C C 4 )alkyl radical optionally bearing at least one hydroxyl group;
  • R 2 N-S(0) 2 - in which the radicals R, which may be identical or different, represent a hydrogen atom or a (C C 4 )alkyl radical optionally bearing at least one hydroxyl group;
  • a carboxylic radical in acid or salified form preferably with an alkali metal or a substituted or unsubstituted ammonium
  • alkyr radical is a saturated linear or branched C Ci 6 , preferably C C 8 hydrocarbon-based radical such as methyl or ethyl;
  • the term "optionally substituted" applied to the alkyl radical implies that said alkyl radical may be substituted with one or more radicals chosen from the following groups: i) hydroxyl, ii) (C C 4 )alkoxy, iii) acylamino, iv) amino optionally substituted with one or two identical or different (CrC 6 )alkyl radicals, the said alkyl radicals possibly forming with the nitrogen atom that bears them a 5- to 7-membered heterocycle optionally comprising another nitrogen or non-nitrogen heteroatom; v) or a quaternary ammonium group -N + R'R"R"', M " for which R', R" and R'", which may be identical or different, represent a hydrogen atom or a (d-C 6 )alkyl group, or alternatively -N + R'R"R"' forms a heteroaryl such as imidazolium optionally substituted with a (CrC 6 )alkyl
  • an "alkoxy" radical is an alkyl-oxy or alkyl-O- radical for which the alkyl radical is a linear or branched C Ci 6 and preferentially C C 8 hydrocarbon-based radical;
  • an "alkylthio" radical is an alkyl-S- radical for which the alkyl radical is a linear or branched C Ci 6 and preferentially C C 8 hydrocarbon-based radical;
  • halogen atom preferentially a chlorine atom
  • an amido radical such as -C(0)-NH 2 ;
  • an amido group such as -C(0)-NH 2 ;
  • R 2 or R 4 represent, independently of each other:
  • ⁇ a hydrogen atom ⁇ a halogen atom, preferentially a chlorine atom;
  • alkyl carboxylate group such as -C(0)-0-R 5 with R 5 representing a (C C 4 )alkyl group
  • the resorcinol derivatives of formula (I) are those in which:
  • R 4 represents a hydrogen atom
  • a halogen preferentially a chlorine atom
  • resorcinol derivatives of formula (I) according to the invention are chosen from the following compounds:
  • the resorcinol derivatives of formula (I) are chosen from compounds 1 to 11 as defined in the preceding table.
  • the resorcinol derivative(s) are synthetic, natural, or are found in natural extracts.
  • the resorcinol derivative(s) of formula (I) are present in the composition in the absence of oxidizing agent or of coupler.
  • oxidation dyes are present, optionally with couplers, it being understood that the oxidation base is other than para-phenylenediamine.
  • the resorcinol derivative(s) of formula (I) are in a total concentration very much higher than at least ten times the concentration of other oxidation dye precursors such as the bases that may be present in the mixture.
  • the resorcinol derivative(s) are present in the composition or in the process according to the invention in a concentration of between 10 "4 and 10 "1 mol per 100 g (%) of the composition containing the resorcinol derivative(s) or the extract(s) comprising them, particularly between 10 "4 and 5 ⁇ 10 "2 mol% and preferentially between 0.01 and 0.025 mol%.
  • sulfate salt ii)
  • sulfates means salts derived from sulfuric acid H 2 S0 4 of which the sulfate ion is S0 4 2" (see “Sulfites, Thiosulfates, and Dithionites” in Ullmann's Encyclopedia of Industrial Chemistry; 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim - http://onlinelibrary.wiley.com/doi/10.1002/14356007.a25_477/pdf).
  • the pH of the sulfates according to the invention is neutral or even slightly acidic (pH between 7 and 6.6).
  • the sulfates are sulfates of formula M 2 S0 3 or M'S0 3 or hydrogen sulfate of formula MHSO 3 with M representing an alkali metal such as Na, K or (di)(CrC 6 )(alkyl)ammonium or tri(Ci-C 6 )alkylammonium such as NH 4 + .
  • the sulfates of the invention are in particular alkali metal or alkaline-earth metal or ammonium, (di)(CrC 6 )alkylammonium or tri(CrC 6 )alkylammonium salts; preferentially, the cationic counterion of the sulfate is chosen from sodium, potassium and ammonium.
  • the sulfate salts according to the invention are chosen from:
  • the sulfate salts used in the composition or in the process of the invention represent from 0.001 % to 10% by weight approximately relative to the total weight of the composition(s) containing this or these metal sulfates, and even more preferentially from 0.05% to 0.1 % by weight approximately.
  • the sulfate salt(s) used in the composition or in the process of the invention represent between 0.25 and 10 mol%, particularly between 0.5 and 10 mol%; between 2 and 10 mol%; and between 0.5 and 10 mol%.
  • Hi oxidizing agent: In the context of the present invention, the process of the invention may be performed in the absence of chemical oxidizing agent, i.e. under the action of atmospheric oxygen.
  • the said process uses a chemical oxidizing agent.
  • chemical oxidizing agent means:
  • alkali metal or quaternary ammonium persalts such as perborates, persulfates, percarbonates or peroxodiphosphates or Oxone®; the oxidizing agent is particularly chosen from sodium perborate, sodium persulfate, potassium persulfate, ammonium persulfate, sodium percarbonate and potassium percarbonate; c) C1-C4 aliphatic and C6-C20 aromatic organic peracids and percarboxylate forms thereof, such as performic acid, peracetic acid, perbenzoic acid derivatives, trifluoroacetic acid, peroxyphthalic acid, peroxymaleic acid and peroxypropionic acid; particularly, the oxidizing agent is peracetic acid;
  • organic peroxides such as dioxirane, C C 6 alkyl peroxides, benzoyl peroxide, peroxo(CrC 6 )alkyl carboxylates, bis(tri)(CrC 6 )alkylsilyl peroxides such as bis(trimethylsilyl) peroxide, C C 6 alkyl peroxydicarbonates, and sodium nonanoyloxybenzene sulfonate as described in patents WO 1995/000 625 and US 4 412 934;
  • organic peroxides such as dioxirane, C C 6 alkyl peroxides, benzoyl peroxide, peroxo(CrC 6 )alkyl carboxylates, bis(tri)(CrC 6 )alkylsilyl peroxides such as bis(trimethylsilyl) peroxide, C C 6 alkyl peroxydicarbonates, and sodium nonanoyloxybenzene sulfonate as described in
  • oxidizing anions such as nitrites, nitrates, hypochlorites, hypobromites, hypoiodites, chlorites, bromites, iodites, chlorates, bromates, iodates and periodates;
  • the oxidizing agent is chosen from an alkali metal hypochlorite or periodate such as sodium hypochlorite or sodium periodate;
  • N-oxy such as the radical 2,2,6,6-tetra(CrC 6 )alkylpiperidino- oxy, 2,2,6,6-tetra(Ci-C 6 )alkylmorpholino-oxy, Fremy nitrosodisulfonate salts, morpholine N-oxide; in particular, the oxidizing agent is chosen from the radical 2,2,6,6-tetramethylpiperidinyloxy;
  • multivalent iodine derivatives such as iodotriacetate, iodosobenzene, iodobenzenetriacetate, iodoperbenzoic acid derivatives, periodinanes, alkyls and benzoylhypoiodites.
  • the oxidizing agent is chosen from iodotriacetate, iodosobenzene, iodobenzenetriacetate, iodoperbenzoic acid and Dess-Martin periodinane.
  • the optional supports for these oxidizing agents a) to h) may be chosen from silica, alumina, charcoal and charged or neutral polymers.
  • i-2) polymeric complexes that can release hydrogen peroxide such as polyvinylpyrrolidone/H 2 0 2 in particular in the form of powders, and the other polymeric complexes described in US 5 008 093; US 3 376 110; US 5 183 901 ; i-3) oxidases that produce hydrogen peroxide in the presence of a suitable substrate (for example glucose in the case of glucose oxidase or uric acid with uricase);
  • a suitable substrate for example glucose in the case of glucose oxidase or uric acid with uricase
  • metal peroxides that generate hydrogen peroxide in water, for instance calcium peroxide or magnesium peroxide;
  • the chemical oxidizing agent(s) are chosen from i) hydrogen peroxide or systems for generating hydrogen peroxide, more particularly H 2 0 2 .
  • the process uses one or more system(s) that generate hydrogen peroxide, chosen from i) urea peroxide, i-2) polymeric complexes that can release hydrogen peroxide, chosen from polyvinylpyrrolidone/H 2 0 2 ; i-3) oxidases; i-v) perborates and i-vi) percarbonates.
  • composition according to the invention comprises hydrogen peroxide.
  • composition(s) comprising the hydrogen peroxide or hydrogen peroxide generators may also contain various adjuvants conventionally used in hair dye compositions and as defined hereinbelow under the section entitled "cosmetic composition”.
  • the hydrogen peroxide used or the system(s) used that generate hydrogen peroxide preferably represent from 0.001 % to 12% by weight expressed as hydrogen peroxide relative to the total weight of the composition(s) containing them. More particularly, the concentration of 20-volumes aqueous hydrogen peroxide solution is between 0.01 and 0.15 mol per 100 g (%) composition of the composition containing the peroxide; preferentially between 10 "4 and 5 ⁇ 10 "1 mol% and especially between 0.0125 and 0.25 mol%. iv) basifying agent
  • the basifying agent present in the composition according to the invention or used in the dyeing process according to the invention as fourth ingredient iv) is an agent for increasing the pH of the composition(s) in which it is present and which is different from the sulfate salts as defined previously.
  • the basifying agent is a Bronsted, Lowry or Lewis base. It may be mineral or organic.
  • the said agent is chosen from i) (bi)carbonates, ii) aqueous ammonia, iii) alkanolamines such as monoethanolamine, diethanolamine, triethanolamine and derivatives thereof, iv) oxyethylenated and/or oxypropylenated ethylenediamines, v) mineral or organic hydroxides, vi) alkali metal silicates such as sodium metasilicate, vii), amino acids, preferably basic amino acids such as arginine, lysine, ornithine, citrulline and histidine, and viii) the compounds of formula (II) below:
  • W is a divalent group (Ci-Cio)alkylene optionally interrupted with at least one heteroatom such as O, S or NR e , and/or the said alkylene group is optionally substituted with at least one hydroxyl group or a radical (C C 4 )alkyl;
  • R a , R b , R c , R d and R e which may be identical or different, represent a hydrogen atom, (C C 4 )alkyl or C C 4 hydroxyalkyl, preferentially a propylene group.
  • the mineral or organic hydroxides are preferably chosen from a) hydroxides of an alkali metal, b) hydroxides of an alkaline-earth metal, for instance sodium hydroxide or potassium hydroxide, c) hydroxides of a transition metal, such as hydroxides of metals from groups III, IV, V and VI, d) hydroxides of lanthanides or actinides, quaternary ammonium hydroxides and guanidinium hydroxide.
  • the hydroxide may be formed in situ, for instance guanidine hydroxide, by reacting calcium hydroxide and guanidine carbonate.
  • bicarbonates also known as hydrogen carbonates, of the following formulae:
  • the alkaline agent is chosen from alkali metal or alkaline-earth metal
  • These hydrogen carbonates may originate from a natural water, for example source water of the Vichy basin, La Roche Posay water, or Badoit water (cf. for example patent FR 2 814 943).
  • sodium carbonate [497-19-8] Na 2 C0 3
  • sodium hydrogen carbonate or sodium bicarbonate [144-55-8] NaHC0 3
  • sodium dihydrogen carbonate Na(HC0 3 ) 2 .
  • the basifying agent(s) iv) are chosen from i) bicarbonates, particularly alkali metal or ammonium bicarbonates, ii) aqueous ammonia, iii) alkanolamines such as ethanolamine or 2-amino-2-methyl-1-propanol, more preferentially aqueous ammonia.
  • the basifying agent(s) as defined previously preferably represent from 10 "3 to 2.5 ⁇ 10 "1 mol per 100 g (%) of the composition containing the said basifying agents, particularly from 0.05 to 0.5 mol% and preferentially from 0.1 to 0.25 g% by weight of the composition. v) optionally one or more mordants
  • the composition according to the invention may also contain a mordant or a mordanting agent that is conventionally used in the textile industry and that is cosmetically acceptable, preferentially in the form of metal salts such as iron, aluminium, titanium, calcium, manganese, copper, zinc or strontium salts.
  • the mordant may be iron sulfate, iron gluconate, iron chloride, iron acetate, manganese gluconate, copper sulfate, iron gluconate, copper, copper chloride, copper acetate, zinc gluconate, calcium chloride, magnesium chloride, potassium titanyl oxalate or strontium acetate.
  • the mordant used is iron sulfate.
  • the mordants may particularly be present in the composition in proportions of between 0.001 % and 10% relative to the total weight of the composition containing them.
  • neither the dyeing process nor the composition of the invention uses or contains a mordanting agent.
  • water is preferably included in the process of the invention. It may originate from the moistening of the keratin fibres and/or from the composition(s) comprising compounds i) to iv) as defined previously or from one or more other compositions. Preferably, the water comes from at least one composition comprising at least one compound chosen from i) to iv) as defined previously.
  • Cosmetic compositions :
  • compositions according to the invention are cosmetically acceptable, i.e. they comprise a dye support that generally contains water or a mixture of water and of one or more organic solvents or a mixture of organic solvents.
  • organic solvent means an organic substance that is capable of dissolving or dispersing in another substance without chemically modifying it.
  • organic solvents examples include C C 4 lower alcohols, such as ethanol and isopropanol; polyols and polyol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, hexylene glycol, and also aromatic alcohols, for instance benzyl alcohol or phenoxyethanol.
  • C C 4 lower alcohols such as ethanol and isopropanol
  • polyols and polyol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, hexylene glycol, and also aromatic alcohols, for instance benzyl alcohol or phenoxyethanol.
  • the organic solvents are present in proportions preferably of between 1 % and 40% by weight approximately and even more preferentially between 5% and 30% by weight approximately relative to the total weight of the dye composition.
  • Adjuvants :
  • composition(s) of the dyeing process in accordance with the invention may also contain various adjuvants conventionally used in hair dye compositions, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof, mineral or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrants, sequestrants, fragrances, buffers, dispersants, conditioning agents, for instance volatile or non-volatile, modified or unmodified silicones, film-forming agents, ceramides, preserving agents and opacifiers.
  • adjuvants conventionally used in hair dye compositions, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwit
  • the said adjuvants are preferably chosen from surfactants such as anionic or nonionic surfactants or mixtures thereof and mineral or organic thickeners.
  • the above adjuvants are generally present in an amount for each of them of between 0.01 % and 40% by weight relative to the weight of the composition, and preferably between 0.1 % and 20% by weight relative to the weight of the composition.
  • ingredients i) to iv) as defined previously or the cosmetic composition according to the invention comprising ingredients i) to iv) as defined previously may also use or comprise one or more additional direct dyes.
  • These direct dyes are chosen, for example, from those conventionally used in direct dyeing, and among which mention may be made of any commonly used aromatic and/or non-aromatic dye such as neutral, acidic or cationic nitrobenzene direct dyes, neutral, acidic or cationic azo direct dyes, natural direct dyes other than ortho-diphenols, neutral, acidic or cationic quinone and in particular anthraquinone direct dyes, azine, triarylmethane, indoamine, methine, styryl, porphyrin, metalloporphyrin, phthalocyanin, cyanin and methine direct dyes, and fluorescent dyes. All these additional dyes are other than the ortho-diphenol derivatives according to the invention.
  • the additional direct dye(s) used in the composition(s) preferably represent from 0.001 % to 10% by weight approximately relative to the total weight of the composition(s) containing them, and even more preferentially from 0.05% to 5% by weight approximately.
  • compositions of the process using ingredients i) to iv) as defined previously or the cosmetic composition according to the invention comprising ingredients i) to iv) as defined previously may also use or comprise one or more oxidation bases and/or one or more couplers conventionally used for the dyeing of keratin fibres.
  • oxidation bases mention may be made of para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols, bis-para-aminophenols, ortho- aminophenols and heterocyclic bases, and the addition salts thereof.
  • couplers mention may be made especially of meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers and heterocyclic couplers, and the addition salts thereof.
  • the oxidation base(s) present in the composition(s) are each generally present in an amount of between 0.001 % and 10% by weight relative to the total weight of the corresponding compositions.
  • the oxidation bases especially aromatic amines such as para- phenylenediamines and/or para-aminophenols
  • they are present in amounts such that the ratio between the amount of resorcinol derivatives of formula (I) as defined previously/the amount of oxidation base is at least greater than 5; preferentially greater than 10 and more preferentially greater than 20.
  • the dyeing process and the composition according to the invention do not comprise para-phenylenediamines and/or para-aminophenols.
  • the cosmetic composition(s) of the invention may be in various galenical forms, such as a powder, a lotion, a mousse, a cream or a gel, or in any other form that is suitable for dyeing keratin fibres. They may also be conditioned in a pump-action bottle without a propellant or under pressure in an aerosol can in the presence of a propellant and form a mousse. pH of the composition(s)
  • the pH of the composition(s) containing iv) the basifying agent(s) is greater than 7, preferably between 8 and 12 and particularly between 8 and 10.
  • the pH of the composition(s) containing the oxidizing agent is preferably less than 7 and more particularly between 1 and 5.
  • composition(s) containing the resorcinol derivative(s) of formula (I) as defined previously and not containing any basifying agent have a pH of less than 7 and preferably between 3 and 6.5.
  • compositions containing the sulfate salt(s), containing or not containing a basifying agent have a pH of greater than 7 and preferably between 8 and 12.
  • compositions may be adjusted to the desired value by means of acidifying or basifying agents usually used in the dyeing of keratin fibres as defined in "iv basifying agent' previously, or alternatively using standard buffer systems.
  • acidifying agents for the compositions mention may be made more particularly of those chosen from a salt derived from i) hydrochloric acid HCI, ii) hydrobromic acid HBr, iii) sulfuric acid H 2 S0 4 , iv) alkylsulfonic acids: Alk-S(0) 2 OH such as methanesulfonic acid and ethanesulfonic acid; v) arylsulfonic acids: Ar-S(0) 2 OH such as benzenesulfonic acid and toluenesulfonic acid; vi) citric acid; vii) succinic acid; viii) tartaric acid; ix) lactic acid; x) alkoxysulfinic acids: Alk-0-S(0)OH such as methoxysulfinic acid and ethoxysulfinic acid; xi) aryloxysulfinic acids such as tolueneoxysulfinic acid and phenoxysulfinic acid;
  • the dyeing process is performed, in one or more steps, by applying to keratin fibres one or more cosmetic compositions containing, taken together or separately in said composition(s), the following ingredients:
  • oxidizing agent preferably a chemical oxidizing agent
  • the pH of the composition comprising ingredient(s) iv) is basic, i.e. greater than 7; preferentially between 7.5 and 12; and
  • the leave-on time between the steps of applying the compositions comprising ingredients i), ii), iii) and/or iv) is set at between 3 and 120 minutes, preferentially between 10 and 60 minutes and more particularly between 15 and 45 minutes.
  • the keratin fibres may or may not be moistened beforehand.
  • the chemical oxidizing agent(s) such as hydrogen peroxide iii) are:
  • One particular embodiment of the invention concerns processes for dyeing in one or two steps.
  • the process for dyeing keratin fibres is performed in a single step by applying to the keratin fibres the cosmetic composition according to the invention, which is preferentially aqueous, comprising:
  • the pH of the composition is basic, i.e. greater than 7; preferentially between 7.5 and 12; and
  • the composition does not contain para- phenylenediamine.
  • the leave-on time after application is generally set at between 5 minutes and 24 hours, particularly between 10 and 120 minutes and more particularly between 15 and 60 minutes, especially between 15 and 45 minutes.
  • the process for dyeing keratin fibres is performed in two steps.
  • the two-step process comprises in the first step the application to the said keratin fibres of a cosmetic composition comprising ingredients i), ii) and iv) as defined previously, and then, in a second step, a cosmetic composition comprising ingredient iii) at least one chemical oxidizing agent as defined previously is applied to said fibres, it being understood that at least one of the two cosmetic compositions is aqueous.
  • the first step consists in applying to the said fibres a composition comprising ingredients i) and iv) as defined previously, and then, in a second step, a second cosmetic composition comprising ingredients ii) and iii) as defined previously is applied to the said fibres, it being understood that preferably at least one of the two compositions is aqueous.
  • One advantageous aspect concerns the dyeing process as described previously preceded by one or more mordanting steps by first treating the keratin fibres with at least one mordant as defined previously (see “v) optionally one or more mordants”).
  • the mordant(s) are especially in a cosmetic composition and are applied at least 5 minutes before performing the dyeing process comprising ingredients i) to iv) as defined previously.
  • the mordant used is iron sulfate.
  • Another advantageous aspect concerns the dyeing process as described previously followed by post-treatment steps such as shampooing using a standard shampoo, rinsing, for example with water, and/or drying the keratin fibres by heat treatment as defined below.
  • the dyeing process according to the invention is performed in one step by applying to the keratin fibres the composition according to the invention comprising ingredients i) to iv) as defined previously, followed by post-treatment steps of rinsing, for example with water, of shampooing with a standard shampoo and/or of drying the keratin fibres.
  • the application temperature is generally between room temperature (15 to 25°C) and 150°C, particularly between 15 and 85°C and preferentially between 20 and 60°C.
  • the head of hair may advantageously be subjected to a heat treatment by heating to a temperature of between 30 and 60°C.
  • this operation may be performed using a styling hood, a hairdryer, an infrared ray dispenser or other standard heating appliances.
  • heating iron at a temperature of between 60 and 220°C and preferably between 120 and 200°C.
  • One particular mode of the invention concerns a dyeing process that is performed at room temperature (25°C).
  • compositions mentioned are ready-to-use compositions that may result from the extemporaneous mixing of two or more compositions and especially of compositions present in dyeing kits.
  • kits comprises from 2 to 5 compartments containing from 2 to 5 compositions among which are distributed the following ingredients: i) at least one resorcinol derivative of formula (I) as defined previously, ii) at least one sulfate salt as defined previously, iii) at least one chemical oxidizing agent such as hydrogen peroxide, and iv) at least one basifying agent as defined previously.
  • the kit comprises five compartments, the first four compartments comprising, respectively, the powdered ingredients i), ii), iii) and iv) as defined previously and the fifth compartment containing an aqueous composition such as water.
  • the compound(s) iii) are hydrogen peroxide precursors.
  • the kit comprises four compartments, the first three compartments comprising, respectively, the powdered ingredients i), ii) and iv) as defined previously and the fourth compartment containing an aqueous composition such as water.
  • Another variant concerns a four-compartment kit, at least one of which compartments contains an aqueous composition, and comprising ingredients i) to iv) as defined previously.
  • Another preferred embodiment concerns a device comprising three compartments: (a) a first compartment contains a composition containing:
  • a second compartment contains a composition containing:
  • At least one chemical oxidizing agent such as hydrogen peroxide
  • At least one of the three compositions is preferably aqueous and the resorcinol derivative(s) of formula (I) may be in powder form.
  • a three-compartment kit the first a) containing a composition comprising i) at least one resorcinol derivative of formula (I) and ii) at least one sulfate salt as defined previously, the second b) containing a composition comprising iii) at least one chemical oxidizing agent such as hydrogen peroxide, and the third c) containing a composition comprising iv) at least one basifying agent as defined previously.
  • At least one of the compositions is preferably aqueous.
  • This composition preferably contains hydrogen peroxide.
  • the kit comprises two compartments: a first compartment comprising a composition containing i) at least one resorcinol derivative of formula (I) as defined previously, ii) at least one sulfate salt as defined previously, iii) at least one chemical oxidizing agent such as hydrogen peroxide, and a second compartment containing iv) at least one basifying agent as defined previously.
  • kits that contain, in a first compartment, a composition comprising compounds i), ii) and iv) as defined previously and, in a second compartment, a composition comprising compound iii) at least one chemical oxidizing agent such as hydrogen peroxide as defined previously.
  • the device according to the invention also comprises an additional composition (c) comprising one or more treating agents.
  • compositions of the device according to the invention are conditioned in separate compartments, optionally accompanied by suitable application means, which may be identical or different, such as fine brushes, coarse brushes or sponges.
  • the device mentioned above may also be equipped with a means for dispensing the desired mixture on the hair, such as the devices described in patent FR 2 586 913.
  • Example 1 The following four compositions were prepared:
  • each composition (A) to (D) obtained is applied to locks of 0.5 g of grey hair containing 90% white hairs. After a leave-on time of 60 minutes at 45°C, the locks are rinsed, washed with a standard shampoo and then dried.
  • compositions of the invention After treatment with the compositions of the invention, the locks are dyed strongly and chromatically, in the absence of para-phenylenediamines. The colorations are very wash-fast and light-fast. Compositions Colours after treatment on a natural lock containing 90% white hairs

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Abstract

La présente invention a pour objet un procédé de coloration de fibres kératiniques, en particulier des cheveux, utilisant i) au moins un dérivé du résorcinol, ii) au moins un sel de sulfate particulier, iii) au moins un agent oxydant et iv) au moins un agent basifiant. Un autre sujet de la présente invention est une composition cosmétique pour la coloration de fibres kératiniques, comprenant les ingrédients i) à iv) tels que définis précédemment. Un autre sujet de l'invention est un dispositif à compartiments multiples comprenant les ingrédients i), ii), iii) et iv). Ce procédé de coloration permet d'obtenir de meilleures colorations, qui sont chromatiques, puissantes et rapides, sans utilisation de bases d'oxydation telles que les para-phénylène diamines et les para-aminophénols.
PCT/EP2011/071744 2010-12-20 2011-12-05 Procédé de coloration de fibres kératiniques utilisant des dérivés du résorcinol, des sels de sulfate, un agent oxydant et un agent basifiant WO2012084473A1 (fr)

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CN201180061013.4A CN103249392B (zh) 2010-12-20 2011-12-05 使用间苯二酚衍生物、硫酸盐、氧化剂和碱化剂对角蛋白纤维进行染色的方法

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FR1060793 2010-12-20
FR1060793A FR2968946B1 (fr) 2010-12-20 2010-12-20 Procede de coloration de fibres keratiniques a partir de derives du resorcinol, de sels de sulfate, d'agents oxydant et d'agent alcalinisant
US201161430269P 2011-01-06 2011-01-06
US61/430,269 2011-01-06

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WO2019046389A1 (fr) * 2017-08-30 2019-03-07 L'oreal Procédés pour améliorer la durabilité de la couleur de cheveux artificiellement colorés
US11707420B2 (en) 2021-08-31 2023-07-25 L'oreal Compositions, kits, and methods for altering the color of hair

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JP6462120B2 (ja) 2014-06-17 2019-01-30 ザ プロクター アンド ギャンブル カンパニー 毛髪の縮れを軽減するための組成物
MX369683B (es) 2014-12-05 2019-10-02 Procter & Gamble Composición para la reducción del encrespado del cabello.
US10632054B2 (en) 2015-04-02 2020-04-28 The Procter And Gamble Company Method for hair frizz reduction
US10660835B2 (en) 2015-04-02 2020-05-26 The Procter And Gamble Company Method for hair frizz reduction
FR3041255B1 (fr) * 2015-09-23 2020-10-16 Oreal Composition de coloration comprenant un coupleur derive du resorcinol, une base d'oxydation.
US10258555B2 (en) 2015-12-04 2019-04-16 The Procter And Gamble Company Composition for hair frizz reduction
WO2017096154A1 (fr) 2015-12-04 2017-06-08 The Procter & Gamble Company Régime de soins capillaires utilisant des compositions comprenant des matériaux de contrôle d'humidité
WO2017173050A1 (fr) 2016-04-01 2017-10-05 The Procter & Gamble Company Composition pour le séchage rapide des cheveux
US10980723B2 (en) 2017-04-10 2021-04-20 The Procter And Gamble Company Non-aqueous composition for hair frizz reduction
FR3090343B1 (fr) * 2018-12-20 2020-12-18 Oreal Procédé de traitement des fibres kératiniques mettant en œuvre une composition comprenant un sel de carnitine ou de dérivé de carnitine comprenant un anion organique aromatique
CN112957269A (zh) * 2021-02-09 2021-06-15 常州大学 一种植物染发剂及其染色方法

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WO2019046389A1 (fr) * 2017-08-30 2019-03-07 L'oreal Procédés pour améliorer la durabilité de la couleur de cheveux artificiellement colorés
US10363208B2 (en) 2017-08-30 2019-07-30 L'oreal Methods for improving the durability of color in artificially colored hair
US11707420B2 (en) 2021-08-31 2023-07-25 L'oreal Compositions, kits, and methods for altering the color of hair

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