WO2016115674A1 - Cosmetic composition for the oxidation dyeing of keratin fibres comprising a cationic polymer and a particular combination of surfactants - Google Patents
Cosmetic composition for the oxidation dyeing of keratin fibres comprising a cationic polymer and a particular combination of surfactants Download PDFInfo
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- WO2016115674A1 WO2016115674A1 PCT/CN2015/071080 CN2015071080W WO2016115674A1 WO 2016115674 A1 WO2016115674 A1 WO 2016115674A1 CN 2015071080 W CN2015071080 W CN 2015071080W WO 2016115674 A1 WO2016115674 A1 WO 2016115674A1
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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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/731—Cellulose; Quaternized cellulose derivatives
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- 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
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/54—Polymers characterized by specific structures/properties
- A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
- A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
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- 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
- A61K2800/882—Mixing prior to application
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- 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 cosmetic composition for the oxidation dyeing of keratin fibres, in particular human keratin fibres such as the hair.
- a subject of the present invention is a dyeing cosmetic composition
- a dyeing cosmetic composition comprising one or more oxidation dyes, one or more cationic polymers and a particular combination of surfactants.
- the present invention also relates to a process for dyeing keratin fibres, in particular human keratin fibres such as the hair, using the composition according to the invention.
- the present invention relates to a kit for the oxidation dyeing of keratin fibres, which is suitable for performing the process of the invention.
- oxidation dyeing methods also known as oxidation dyeing, which use dye compositions containing oxidation dye precursors, generally referred to as oxidation bases, such as ortho-or para-phenylenediamines, ortho-or para-aminophenols and heterocyclic compounds, have been developed for dyeing human keratin fibres in a long-lasting manner.
- oxidation bases are colourless or weakly coloured compounds, which, when combined with oxidizing products, may give rise to coloured compounds via a process of oxidative condensation.
- couplers or coloration modifiers the latter being chosen especially from aromatic meta-diaminobenzenes, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as indole compounds.
- compositions known in the prior art mention may be made of WO 2011/138838 which discloses a ready-to-use composition for the oxidation dyeing of keratin fibers comprising, in an aqueous medium at least one oxidation dye, at least one oxidizing agent, and at least 1.5% by weight of at least one amphoteric surfactant.
- the prior art compositions are not entirely satisfactory, and their performance qualities can be further improved, in particular as regards the working qualities (whether or not the composition is mixed with an oxidizing composition before application) , especially in terms of texture, ease of application and ease of spreading of the composition on the keratin fibres.
- the compositions of the prior art are not always sufficiently stable, and their coloring performances can also be further improved, especially in terms of intensity, homogeneity and selectivity of the dyeing obtained.
- One subject of the present invention is thus a cosmetic composition for the oxidation dyeing of keratin fibres comprising:
- non ionic surfactant chosen from alkanolamides of C 6 -C 30 fatty acids
- composition according to the invention has very good working qualities, and especially a particularly pleasant texture and a good viscosity (neither too thick, nor too fluid which facilitates its use) .
- This property is very stable over the time, and does not diminish even after several months of storage at ambient temperature (25°C) as well as from low temperatures (such as 4°C) until high temperatures (such as 45°C) .
- the composition further exhibits excellent foaming properties similar to those of a shampoo, whenever or not is mixed with a developer composition (or oxidizer) , and it is very easy to apply and to spread on the locks of hair, in particular from the roots to the ends. More particularly, the composition of the present invention allows an easy an rapid formation of foam, such as immediately after massaging the hair. The foam is firm and creamy and allows a good dyeing performance. Moreover, the foam stays on the hair without flying away.
- composition of the invention does not require premixing with a developer composition or oxidizing composition or oxidizer. It allows to be used simultaneously with a developer or oxidizer directly on the hair, without a step of premixing.
- composition of the invention has very good cosmetic properties, and provides the keratin fibres with an excellent conditioning.
- the hair is shiny, smooth, supple and easy to disentangle.
- composition according to the invention has superior dyeing quality, especially in terms of intensity, homogeneity and selectivity of the dyeing obtained.
- composition of the invention is intended to be used in a process for dyeing keratin fibres either as a ready-to-use composition when it contains an oxidizing agent, or in combination with an oxidizing composition.
- a subj ect of the invention is thus also a process for dyeing keratin fibres, which consists in applying to the keratin fibres the composition of the invention. Said composition may be applied sequentially to or simultaneously with an oxidizing composition comprising one or more oxidizing agents.
- oxyalkylenated covers, respectively, mono-or poly-oxyalkylenated, oxyethylenated, oxypropylenated and glycerolated compounds, unless specifically mentioned.
- the composition of the invention is advantageously transparent.
- the transparency of the composition may be characterized by measuring its turbidity according to the NTU method using a 2100P model turbidimeter from the company Hach, at room temperature.
- the turbidity of the compositions of the invention is generally less than 400 NTU units and preferably less than 250 NTU units, more preferably less than 200 NTU.
- composition according to the invention comprises one or more oxidation dyes.
- oxidation dyes that may be used in the present invention are generally chosen from oxidation bases, optionally combined with one or more couplers.
- the oxidation dye (s) comprise one or more oxidation bases.
- the oxidation bases may be chosen especially from para-phenylenediamines, bis (phenyl) alkylenediamines, para-aminophenols, ortho-aminophenols, heterocyclic bases, and the addition salts thereof, and mixtures thereof.
- para-phenylenediamines examples that may be mentioned include para-phenylenediamine, para-tolylenediamine, 2-chloro-para-phenylenediamine, 2, 3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2, 6-diethyl-para-phenylenediamine, 2, 5-dimethyl-para-phenylenediamine, N, N- dimethyl-para-phenylenediamine, N, N-diethyl-para-phenylenediamine, N,N-dipropyl-para-phenylenediamine, 4-amino-N, N-diethyl-3-methylaniline, N, N-bis ( ⁇ -hydroxyethyl) -para-phenylenediamine, 4-N,N-bis ( ⁇ -hydroxyethyl) amino-2-methylaniline, 4-N, N–bis ( ⁇ -hydroxyethyl) amino-2-chloroaniline
- para-phenylenediamine para-tolylenediamine, 2-isopropyl-para-phenylenediamine, 2- ⁇ -hydroxyethyl-para-phenylenediamine, 2- ⁇ -hydroxyethyloxy-para-phenylenediamine, 2, 6-dimethyl-para-phenylenediamine, 2, 6-diethyl-para-phenylenediamine, 2, 3-dimethyl-para-phenylenediamine, N, N-bis ( ⁇ -hydroxyethyl) -para-phenylenediamine, 2-chloro-para-phenylenediamine and 2- ⁇ -acetylaminoethyloxy-para-phenylenediamine, and the addition salts thereof with an acid, are particularly preferred.
- the bis (phenyl) alkylenediamines examples include N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4'-aminophenyl) -1, 3-diaminopropanol, N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis(4'-aminophenyl) ethylenediamine, N, N'-bis (4-aminophenyl) tetramethylenediamine, N, N'-bis ( ⁇ -hydroxyethyl) -N, N'-bis (4-aminophenyl) tetramethylenediamine, N, N'-bis (4-methylaminophenyl) tetramethylenediamine, N, N'-bis (ethyl) -N, N'- bis (4'-amino-3'-methylphenyl) ethylenediamine, 1, 8-bis (2, 5-diaminophenoxy)
- para-aminophenols examples that may be mentioned include para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-chlorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- ( ⁇ -hydroxyethyl-aminomethyl) phenol and 4-amino-2-fluorophenol, and the addition salts thereof with an acid.
- ortho-aminophenols examples that may be mentioned include 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol and 5-acetamido-2-aminophenol, and the addition salts thereof.
- heterocyclic bases examples that may be mentioned include pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
- pyridine derivatives that may be mentioned are the compounds described, for example, in patents GB 1 026 978 and GB 1 153 196, for instance 2, 5-diaminopyridine, 2- (4-methoxyphenyl) amino-3-aminopyridine and 3, 4-diaminopyridine, and the addition salts thereof.
- pyridine oxidation bases that are useful in the present invention are the 3-aminopyrazolo [1, 5-a] pyridine oxidation bases or the addition salts thereof described, for example, in patent application FR 2 801 308.
- Examples that may be mentioned include pyrazolo [1, 5-a]pyrid-3-ylamine, 2- (acetylamino) pyrazolo [1, 5-a] pyrid-3-ylamine, 2-(morpholin-4-yl) pyrazolo [1, 5-a] pyrid-3-ylamine, 3-aminopyrazolo [1, 5-a] pyridine-2-carboxylic acid, 2-methoxypyrazolo [1, 5-a] pyrid-3-ylamine, (3-aminopyrazolo [1, 5-a]pyrid-7-yl) methanol, 2- (3-aminopyrazolo [1, 5-a] pyrid-5-yl) ethanol, 2-(3-aminopyrazolo [
- pyrimidine derivatives that may be mentioned are the compounds described, for example, in the patents DE 2359399; JP 88-169571; JP 05-63124; EP 0770375 or patent application WO 96/15765, such as 2, 4, 5, 6-tetraaminopyrimidine, 4-hydroxy-2, 5, 6-triaminopyrimidine, 2-hydroxy-4, 5, 6-triaminopyrimidine, 2, 4-dihydroxy-5, 6-diaminopyrimidine, 2, 5, 6-triaminopyrimidine and the addition salts thereof and the tautomeric forms thereof, when a tautomeric equilibrium exists.
- pyrazole derivatives that may be mentioned are the compounds described in patents DE 3843892 and DE 4133957 and patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988, for instance 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, 4-amino-1, 3-dimethyl-5-hydrazinopyrazole, 1-benzyl-4, 5-diamino-3-methylpyrazole, 4, 5-diamino-3-tert-butyl-1-methyl
- a 4, 5-diaminopyrazole will preferably be used, and even more preferentially 4, 5-diamino-1- ( ⁇ -hydroxyethyl) pyrazole and/or a salt thereof.
- Pyrazole derivatives that may also be mentioned include diamino-N, N-dihydropyrazolopyrazolones and especially those described in patent application FR-A-2 886 136, such as the following compounds and the addition salts thereof: 2, 3-diamino-6, 7-dihydro-1H,5H-pyrazolo [1, 2-a] pyrazol-1-one, 2-amino-3-ethylamino-6, 7-dihydro-1H, 5H-pyrazolo [1, 2-a] pyrazol-1-one, 2-amino-3-isopropylamino-6, 7-dihydro-1H, 5H-pyrazolo [1, 2-a] pyrazol-1-one, 2-amino-3- (pyrrolidin-1-yl) -6, 7-dihydro-1H, 5H-pyrazolo [1, 2-a] pyrazol-1-one, 4, 5-diamino-1, 2-dimethyl-1, 2-di
- Use will preferably be made of 2, 3-diamino-6, 7-dihydro-1H,5H-pyrazolo [1, 2-a] pyrazol-1-one and/or one of its salts.
- Heterocyclic bases that will preferentially be used include 4, 5-diamino-1- ( ⁇ -hydroxyethyl) pyrazole and/or 2, 3-diamino-6, 7-dihydro-1H,5H-pyrazolo [1, 2-a] pyrazol-1-one and/or a salt thereof.
- the oxidation dye (s) may also comprise one or more couplers, which may be chosen from those conventionally used for the dyeing of keratin fibres.
- couplers mention may be made especially of meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers heterocyclic couplers, and also the addition salts thereof, and mixtures thereof.
- Examples that may be mentioned include 1, 3-dihydroxybenzene, 1,3-dihydroxy-2-methylbenzene, 4-chloro-1, 3-dihydroxybenzene, 2, 4-diamino-1- ( ⁇ -hydroxyethyloxy) benzene, 2-amino-4- ( ⁇ -hydroxyethylamino) -1-methoxybenzene, 1, 3-diaminobenzene, 1, 3-bis(2, 4-diaminophenoxy) propane, 3-ureidoaniline, 3-ureido-1-dimethylaminobenzene, sesamol, 1- ⁇ -hydroxyethylamino-3, 4-methylenedioxybenzene, ⁇ -naphthol, 2-methyl-1-naphthol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methylindole, 2-amino-3-hydroxypyridine, 6-hydroxybenzomorpholine, 3, 5-diamino-2, 6-dimethoxypyridine, 1-N-
- addition salts of the oxidation bases and couplers that may be used within the context of the invention are especially chosen from the addition salts with an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
- an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
- the oxidation base (s) may advantageously represent from 0.0001% to 10% by weight relative to the total weight of the composition, preferably from 0.005% to 5% by weight and better still from 0.1% to 5% by weight.
- the coupler (s) may advantageously represent from 0.0001% to 10% by weight relative to the total weight of the composition, and preferably from 0.005% to 5% by weight.
- composition of the invention further comprises one or more cationic polymer (s) .
- cationic polymer is intended to mean any polymer comprising cationic groups and/or groups that can be ionized to cationic groups.
- the cationic polymer is hydrophilic or amphiphilic.
- the preferred cationic polymers are chosen from those that contain units comprising primary, secondary, tertiary and/or quaternary amine groups that may either form part of the main polymer chain or may be borne by a side substituent directly connected thereto.
- cationic polymers mention may be made more particularly of:
- -R 3 which may be identical or different, denote a hydrogen atom or a CH 3 group
- -A which may be identical or different, represent a linear or branched divalent alkyl group of 1 to 6 carbon atoms, preferably 2 or 3 carbon atoms, or a hydroxyalkyl group of 1 to 4 carbon atoms;
- R 4 , R 5 and R 6 which may be identical or different, represent an alkyl group containing from 1 to 18 carbon atoms or a benzyl group, and preferably an alkyl group containing from 1 to 6 carbon atoms;
- R 1 and R 2 which may be identical or different, represent a hydrogen atom 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 copolymers of family (1) may also contain one or more units derived from comonomers which may be chosen from the family of acrylamides, methacrylamides, diacetone acrylamides, acrylamides and methacrylamides substituted on the nitrogen with C 1- C 4 alkyls, acrylic or methacrylic acids or esters thereof, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, and vinyl esters.
- crosslinked polymers of methacryloyloxy (C 1 -C 4 )alkyl tri (C 1 -C 4 ) alkylammonium salts such as the polymers obtained by homopolymerization of dimethylaminoethyl methacrylate quaternized with methyl chloride, or by copolymerization of acrylamide with dimethylaminoethyl methacrylate quaternized with methyl chloride, the homo-or copolymerization being followed by crosslinking with an olefinically unsaturated compound, in particular methylenebisacrylamide.
- a crosslinked acrylamide/methacryloyloxyethyltrimethylammonium chloride copolymer (20/80 by weight) in the form of a dispersion comprising 50% by weight of said copolymer in mineral oil may more particularly be used.
- This dispersion is sold under the name SC 92 by the company Ciba.
- a crosslinked methacryloyloxyethyltrimethylammonium chloride homopolymer comprising 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 SC 95 and SC 96 by the company Ciba.
- Cationic polysaccharides in particular cationic celluloses and cationic galactomannan gums.
- cationic polysaccharides mention may be made more particularly of cellulose ether derivatives comprising quaternary ammonium groups, cationic cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer and cationic galactomannan gums.
- cellulose ether derivatives comprising quaternary ammonium groups are in particular described in FR patent 1 492 597, and mention may be made of the polymers sold under the name Ucare Polymer JR (JR 400 LT, JR 125 and JR 30M) or LR (LR 400 or LR 30M) by the company Amerchol. These polymers are also defined in the CTFA dictionary as quaternary ammoniums of hydroxyethylcellulose that have reacted with an epoxide substituted with a trimethylammonium group.
- Cationic cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer are described in particular in US patent 4 131 576, and mention may be made of hydroxyalkyl celluloses, for instance hydroxymethyl-, hydroxyethyl-or hydroxypropylcelluloses grafted, in particular, with a methacryloylethyltrimethylammonium, methacrylamidopropyltrimethyl-ammonium, dimethyldiallylammonium or hydroxypropyltrialkylammonium salt, for example 2-hydroxypropyl trimethyl ammonium chloride.
- hydroxyalkyl celluloses for instance hydroxymethyl-, hydroxyethyl-or hydroxypropylcelluloses grafted, in particular, with a methacryloylethyltrimethylammonium, methacrylamidopropyltrimethyl-ammonium, dimethyldiallylammonium or hydroxypropyltrialkylammoni
- the commercial products corresponding to this definition are more particularly the products sold under the names Celquat L 200 and Celquat H 100 by the company National Starch, or hydroxyethyl cellulose-2-hydroxypropyl trimethyl ammonium chloride ether (INCI name: Polyquaternium-10) such as the product sold under the name Polyquta 400KC by the company KCI.
- guar gums comprising cationic trialkylammonium groups.
- Use is made, for example, of guar gums modified with a 2, 3-epoxypropyltrimethylammonium salt (for example, a chloride) .
- a 2, 3-epoxypropyltrimethylammonium salt for example, a chloride
- Such products are in particular sold under the names Jaguar C 13 S, Jaguar C 15, Jaguar C 17 and Jaguar C 162 by the company Rhodia.
- Water-soluble polyaminoamides prepared in particular by polycondensation of an acidic compound with a polyamine; these polyaminoamides can be crosslinked by an epihalohydrin, a diepoxide, a dianhydride, an unsaturated dianhydride, a bisunsaturated derivative, a bishalohydrin, a bisazetidinium, a bishaloacyldiamine or an alkyl bishalide or alternatively by an oligomer resulting from the reaction of a bifunctional compound reactive with respect to a bishalohydrin, a bisazetidinium, a bishaloacyldiamine, an alkyl bishalide, an epihalohydrin, a diepoxide or a bisunsaturated derivative; the crosslinking agent being used in proportions ranging from 0.025 to 0.35 mol per amine group of the polyaminoamide; these polyaminoamides can be alkylated or, if they comprise one
- Polyaminoamide derivatives resulting from the condensation of polyalkylene polyamines with polycarboxylic acids followed by alkylation with difunctional agents Mention may be made, for example, of adipic acid/dialkylaminohydroxyalkyldialkylenetriamine polymers in which the alkyl group comprises from 1 to 4 carbon atoms and preferably denotes methyl, ethyl or propyl.
- adipic acid/dimethylaminohydroxypropyl/diethylenetriamine polymers sold under the name Cartaretine F, F4 or F8 by the company Sandoz.
- Polymers of this type are sold in particular under the name Hercosett 57 by the company Hercules Inc. or alternatively under the name PD 170 or Delsette 101 by the company Hercules in the case of the adipic acid/epoxypropyl/diethylenetriamine copolymer.
- Cyclopolymers of alkyldiallylamine or of dialkyldiallylammonium such as the homopolymers or copolymers comprising, as main constituent of the chain, units corresponding to formula (PI) or (PII) :
- -R 12 denotes a hydrogen atom or a methyl group
- R 10 and R 11 independently of each other, denote an alkyl group containing from 1 to 6 carbon atoms, a hydroxyalkyl group in which the alkyl group contains 1 to 5 carbon atoms, a C 1 -C 4 amidoalkyl group; or alternatively R 10 and R 11 may denote, together with the nitrogen atom to which they are attached, heterocyclic groups such as piperidyl or morpholinyl; R 10 and R 11 , independently of each other, preferably denote an alkyl group containing from 1 to 4 carbon atoms;
- -Y - is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulfate, bisulfite, sulfate or phosphate.
- R 13 , R 14 , R 15 and R 16 which may be identical or different, represent aliphatic, alicyclic or arylaliphatic groups comprising from 1 to 20 carbon atoms or C 1-4 hydroxyalkylaliphatic groups, or else R 13 , R 14 , R 15 and R 16 , together or separately, form, with the nitrogen atoms to which they are attached, heterocycles optionally comprising a second heteroatom other than nitrogen, or else R 13 , R 14 , R 15 and R 16 represent a linear or branched C 1 -C 6 alkyl group sub stituted by a nitrile, ester, acyl, amide or -CO-O-R 17 -D or -CO-NH-R 17 -D group, where R 17 is an alkylene and D a quaternary ammonium group;
- -A 1 and B 1 represent divalent polymethylene groups comprising from 2 to 20 carbon atoms which may be linear or branched, and saturated or unsaturated, and which may contain, linked to or inserted 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
- a 1 , R 13 and R 15 can form, with the two nitrogen atoms to which they are attached, a piperazine ring.
- a 1 denotes a saturated or unsaturated and linear or branched alkylene or hydroxyalkylene group
- B 1 can also denote a (CH 2 ) n -CO-D-OC- (CH 2 ) n -group in which D denotes:
- a glycol residue of formula -O-Z-O- in which Z denotes a linear or branched hydrocarbon-based group, or a group corresponding to one of the following formulae: - (CH 2 -CH 2 -O) x -CH 2 -CH 2 -and - [CH 2 -CH(CH 3 ) -O] y -CH 2 -CH (CH 3 ) -, where 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;
- a bissecondary diamine residue such as a piperazine derivative
- Y denotes a linear or branched hydrocarbon-based group, or else the divalent group -CH 2 -CH 2 -S-S-CH 2 -CH 2 -;
- X - is an anion, such as chloride or bromide.
- Mn number-average molar mass
- R 1 , R 2 , R 3 and R 4 which may be identical or different, denote an alkyl or hydroxyalkyl group having from 1 to 4 carbon atoms approximately, n and p are integers varying from 2 to 20 approximately and X - is an anion derived from an inorganic or organic acid.
- -R 18 , R 19 , R 20 and R 21 which may be identical or different, represent a hydrogen atom or a methyl, ethyl, propyl, ⁇ -hydroxyethyl, ⁇ -hydroxypropyl or -CH 2 CH 2 (OCH 2 CH 2 ) p OH group, where p is equal to 0 or to an integer of between 1 and 6, with the proviso that R 18 , R 19 , R 20 and R 21 do not simultaneously represent a hydrogen atom,
- -r and s which may be identical or different, are integers between 1 and 6,
- -q is equal to 0 or to an integer between 1 and 34
- -A denotes a radical of a dihalide or preferably represents -CH 2 -CH 2 -O-CH 2 -CH 2 -.
- Examples that may be mentioned include the products A 15, AD 1, AZ 1 and 175 sold by the company Miranol.
- Polyamines such as H sold by Cognis, referred to under the name Polyethylene glycol (15) tallow polyamine in the CTFA dictionary.
- these polymers may be chosen in particular from homopolymers or copolymers comprising one or more units derived from vinylamine and optionally one or more units derived from vinylformamide.
- these cationic polymers are chosen from polymers comprising, in their structure, from 5 mol% to 100 mol% of units corresponding to formula (A) and from 0 to 95 mol% of units corresponding to formula (B) , preferentially from 10 mol% to 100 mol%of units corresponding to formula (A) and from 0 to 90 mol% of units corresponding to formula (B) .
- These polymers may be obtained, for example, by partial hydrolysis of polyvinylformamide. This hydrolysis may be performed in an acidic or basic medium.
- the weight-average molecular weight of said polymer measured by light scattering, may range from 1000 to 3 000 000 g/mol, preferably from 10 000 to 1 000 000 and more particularly from 100 000 to 500 000 g/mol.
- the cationic charge density of these polymers may range from 2 to 20 meq/g, preferably from 2.5 to 15 meq/g and more particularly from 3.5 to 10 meq/g.
- the polymers comprising units of formula (A) and optionally units of formula (B) are sold in particular under the name Lupamin by the company BASF, for instance, in a non-limiting manner, the products sold under the names Lupamin 9095, Lupamin 5095, Lupamin 1095, Lupamin 9030 (or Luviquat 9030) and Lupamin 9010.
- cationic polymers that may be used in the context of the invention are cationic proteins or cationic protein hydrolysates, polyalkyleneimines, in particular polyethyleneimines, polymers comprising vinylpyridine or vinylpyridinium units, condensates of polyamines and of epichlorohydrin, quaternary polyureylenes and chitin derivatives.
- the cationic polymers are chosen from those of family (2) mentioned above.
- Particularly preferred cationic polymers for use in the compositions of the present invention are quaternized hydroxyalkylcelluloses such as quaternized hydroxyethylcelluloses.
- Most particularly preferred polymers are those known under the INCI name of Polyquaternium-10.
- composition of the invention preferably contains from 0.1 to 5% by weight of cationic polymer (s) , more preferably from 0.2 to 2.5%by weight, with regard to the total weight of the composition.
- composition of the invention further comprises one or more amphoteric or zwitterionic surfactant (s) .
- amphoteric or zwitterionic surfactant (s) which are preferably non-silicone, may especially be derivatives of aliphatic secondary or tertiary amines, optionally quaternized, in which derivatives the aliphatic group is a linear or branched chain comprising from 8 to 22 carbon atoms, the said amine derivatives containing at least one anionic group, for instance a carboxylate, sulfonate, sulfate, phosphate or phosphonate group.
- -R a represents a C 10 -C 30 alkyl or alkenyl group derived from an acid R a COOH preferably present in hydrolysed coconut oil, or a heptyl, nonyl or undecyl group;
- -R b represents a beta-hydroxyethyl group
- -M + represents a cationic counterion derived from an alkali metal or alkaline-earth metal, such as sodium, an ammonium ion or an ion derived from an organic amine, and
- -X - represents an organic or mineral anionic counterion, such as that chosen from halides, acetates, phosphates, nitrates, (C 1 -C 4 )alkyl sulfates, (C 1 -C 4 ) alkylsulfonates or (C 1 -C 4 ) alkylarylsulfonates, in particular methyl sulfate and ethyl sulfate; or alternatively M + and X - are absent;
- -B represents the group -CH 2 CH 2 OX'
- -X' represents the group -CH 2 COOH, -CH 2 -COOZ’ ,
- -Z' represents a cationic counterion derived from an alkali metal or alkaline-earth metal, such as sodium, an ammonium ion or an ion derived from an organic amine;
- -R a ’ represents a C 10 -C 30 alkyl or alkenyl group of an acid R a ’-COOH which is preferably present in coconut oil or in hydrolysed linseed oil, or an alkyl group, especially a C 17 group, and its iso form, or an unsaturated C 17 group.
- cocoamphodiacetate sold by the company Rhodia under the trade name C2M Concentrate.
- -Y′′ represents the group -COOH, -COOZ”
- R -R d and R e represent, independently of each other, a C 1 -C 4 alkyl or hydroxyalkyl radical;
- -Z′′ represents a cationic counterion derived from an alkali metal or alkaline-earth metal, such as sodium, an ammonium ion or an ion derived from an organic amine;
- R a ′′ represents a C 10 -C 30 alkyl or alkenyl group of an acid R a ′′ -COOH which is preferably present in coconut oil or in hydrolysed linseed oil;
- -n and n' denote, independently of each other, an integer ranging from 1 to 3.
- amphoteric or zwitterionic surfactants use is preferably made of (C 8 -C 20 ) alkylbetaines, (C 8 -C 20 ) alkylsulfobetaines, (C 8 -C 20 ) alkylamido (C 3 -C 8 ) alkylbetaines and (C 8 -C 20 ) alkylamido (C 6 -C 8 ) alkylsulfobetaines, more preferably of (C 8 -C 20 ) alkylbetaines and even more preferably of cocoylbetaine.
- composition of the invention preferably comprises said amphoteric or zwitterionic surfactant (s) in an amount of from 0.01 to 15% by weight, more preferably from 0.1 to 10% by weight, and even more preferably from 1 to 5% by weight, based on the total weight of the composition.
- composition of the invention further comprises one or more non ionic surfactant (s) chosen from alkanolamides of C 6 -C 30 fatty acids.
- Such surfactants can be chosen from mono-alkanolamides and di-alcanolamides of C 8 -C 30 fatty acids, and preferably from mono-alkanolamides and di-alcanolamides of C 8 -C 18 fatty acids.
- the alkanol groups may have from 1 to 10 carbon atoms, and preferably from 2 to 5 carbon atoms.
- cocamide monoethanolamine cocamide diethanolamine
- cocamide mono-isopropanolamine cocamide mono-isopropanolamine
- said non ionic surfactant is cocamide mono-isopropanolamine.
- composition of the invention preferably comprises said non ionic surfactant (s) chosen from alkanolamides of C 6 -C 30 fatty acids in an amount ranging from 0.05 to 5 % by weight, more preferably from 0.1 to 1 % by weight, with regard to the total weight of the composition.
- non ionic surfactant chosen from alkanolamides of C 6 -C 30 fatty acids in an amount ranging from 0.05 to 5 % by weight, more preferably from 0.1 to 1 % by weight, with regard to the total weight of the composition.
- composition according to the invention further comprises one or more anionic surfactant (s) .
- anionic surfactant means a surfactant comprising, as ionic or ionizable groups, only anionic groups. These anionic groups are preferably chosen from the following groups:
- anionic surfactants that may be used in the composition according to the invention, mention may be made of alkyl sulfates, alkyl ether sulfates, alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates, alkylsulfonates, alkylamidesulfonates, alkylarylsulfonates, ⁇ -olefin sulfonates, paraffin sulfonates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkylamide sulfosuccinates, alkyl sulfoacetates, acylsarcosinates, acylglutamates, alkyl sulfosuccinamates, acylisethionates and N-acyltaurates, polyglycoside polycarboxylic acid and alkyl monoester
- These compounds can be oxyethylenated and then preferably comprise from 1 to 50 ethylene oxide units.
- the salts of C 6 -C 24 alkyl monoesters of polyglycoside-polycarboxylic acids may be chosen from C 6 -C 24 alkyl polyglycoside-citrates, C 6 -C 24 alkyl polyglycoside-tartrates and C 6 -C 24 alkyl polyglycoside-sulfosuccinates.
- anionic surfactant (s) When the anionic surfactant (s) are in salt form, they may be chosen from alkali metal salts such as the sodium or potassium salt and preferably the sodium salt, ammonium salts, amine salts and in particular amino alcohol salts, or alkaline-earth metal salts such as the magnesium salts.
- alkali metal salts such as the sodium or potassium salt and preferably the sodium salt, ammonium salts, amine salts and in particular amino alcohol salts, or alkaline-earth metal salts such as the magnesium salts.
- amino alcohol salts examples include monoethanolamine, diethanolamine and triethanolamine salts, monoisopropanolamine, diisopropanolamine or triisopropanolamine salts, 2-amino-2-methyl-1-propanol salts, 2-amino-2-methyl-1, 3-propanediol salts and tris (hydroxymethyl) aminomethane salts.
- Alkali metal or alkaline-earth metal salts and in particular sodium or magnesium salts, are preferably used.
- Preferred anionic surfactants are chosen from (C 6 -C 30 ) alkyl sulfates, (C 6 -C 30 ) alkyl ether sulfates, (C 6 -C 30 ) alkylamido ether sulfates, alkylaryl polyether sulfates and monoglyceride sulphates, all these compounds optionally comprising from 1 to 20 ethylene oxide units; and more preferably from (C 12 -C 20 ) alkyl sulphates and (C 12 -C 20 ) alkyl ether sulfates comprising from 2 to 20 ethylene oxide units, and even more preferably from 1 to 4 ethylene oxide units, especially in the form of alkali metal, ammonium, amino alcohol and alkaline-earth metal salts, or a mixture of these compounds.
- a polyoxyethylenated sodium lauryl ether sulphate such as sodium lauryl ether sulphate containing 2 or
- the amount of said anionic surfactant (s) in the composition of the invention is of at least 1.5% by weight, more preferably at least 3% by weight, with regard to the total weight of the composition. This amount preferably ranges from 5 to 30% by weight, more preferably from 5 to 15% by weight, with regard to the total weight of the composition.
- composition of the invention may further contain one or more additional non ionic surfactant (s) different from the above-described alkanolamides of C 6 -C 30 fatty acids.
- nonionic surfactant (s) that may be used in the compositions are described, for example, in the Handbook of Surfactants by M. R. Porter, published by Blackie &Son (Glasgow and London) , 1991, pp. 116-178.
- nonionic surfactants examples include the following nonionic surfactants:
- the oxyalkylene units are more particularly oxyethylene or oxypropylene units, or a combination thereof, preferably oxyethylene units.
- the number of moles of ethylene oxide and/or propylene oxide preferably ranges from 1 to 250, more particularly from 2 to 100 and better still from 2 to 50; the number of moles of glycerol ranges especially from 1 to 50 and better still from 1 to 10.
- nonionic surfactants according to the invention do not comprise any oxypropylene units.
- glycerolated nonionic surfactants use is preferably made of monoglycerolated or polyglycerolated C 8 -C 40 alcohols, comprising from 1 to 50 mol of glycerol and preferably from 1 to 10 mol of glycerol.
- 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, oleyl/cetyl alcohol containing 6 mol of glycerol, and octadecanol containing 6 mol of glycerol.
- glycerolated alcohols it is more particularly preferred to use the C 8 /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 additional nonionic surfactant (s) when they are present in the composition of the invention, are preferably present in a total amount ranging from 0.01 to 1% by weight, with regard to the total weight of the composition.
- composition of the invention may further comprise one or more cationic surfactants.
- cationic surfactant means a surfactant that is positively charged when it is contained in the composition according to the invention. This surfactant may bear one or more positive permanent charges or may contain one or more cationizable functions in the compositions.
- the cationic surfactant (s) are preferably chosen from optionally polyoxyalkylenated, primary, secondary or tertiary fatty amines, or salts thereof, and quaternary ammonium salts, and mixtures thereof.
- the fatty amines generally comprise at least one C 8 -C 30 hydrocarbon-based chain.
- quaternary ammonium cationic surfactants those that are preferred are:
- -tetraalkylammonium salts for instance dialkyldimethylammonium or alkyltrimethylammonium salts in which the alkyl group contains approximately from 12 to 22 carbon atoms, in particular behenyltrimethylammonium, distearyldimethylammonium, cetyltrimethylammonium or benzyldimethylstearylammonium salts, or, on the other hand, the palmitylamidopropyltrimethylammonium salt, the stearamidopropyltrimethylammonium salt, the stearamidopropyldimethylcetearylammonium salt, or the stearamidopropyldimethyl (myristyl acetate) ammonium salt sold under the name 70 by the company Van Dyk. It is particularly preferred to use the chloride salts of these compounds.
- -di-or triquaternary ammonium salts for example, Finquat CT-P, available from the company Finetex (Quaternium 89) , and Finquat CT, available from the company Finetex (Quaternium 75) .
- acyl groups preferably contain 14 to 18 carbon atoms and are obtained more particularly from a vegetable oil, such as palm oil or sunflower oil. When the compound contains several acyl groups, these groups may be identical or different.
- Such compounds are, for example, sold under the names by the company Henkel, by the company Stepan, by the company Ceca or WE 18 by the company Rewo-Witco.
- composition according to the invention may contain, for example, a mixture of quaternary ammonium monoester, diester and triester salts with a weight maj ority of diester salts.
- ammonium salts containing at least one ester function that are described in patents US-A-4 874 554 and US-A-4 137 180.
- Use may be made of behenoylhydroxypropyltrimethylammonium chloride, provided by Kao under the name Quatarmin BTC 131.
- the ammonium salts containing at least one ester function contain two ester functions.
- quaternary ammonium salts containing at least one ester function which can be used, it is preferred to use dipalmitoylethylhydroxyethylmethylammonium salts.
- composition of the present invention may further contain one or more fatty substances.
- fatty sub stance means an organic compound that is insoluble in water at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg) (solubility of less than 5% by weight, preferably less than 1% and even more preferentially less than 0.1%) . They have in their structure at least one hydrocarbon-based chain comprising at least 6 carbon atoms or a sequence of at least two siloxane groups.
- the fatty substances are generally soluble in organic solvents under the same temperature and pressure conditions, for instance chloroform, dichloromethane, carbon tetrachloride, ethanol, benzene,toluene, tetrahydrofuran (THF) , liquid petroleum j elly or decamethylcyclopentasiloxane.
- organic solvents for instance chloroform, dichloromethane, carbon tetrachloride, ethanol, benzene,toluene, tetrahydrofuran (THF) , liquid petroleum j elly or decamethylcyclopentasiloxane.
- the fatty substances are chosen from C 6 -C 16 hydrocarbons, hydrocarbons containing more than 16 carbon atoms, non-silicone oils of animal origin, plant or synthetic oils of triglyceride type, fluoro oils, fatty alcohols, fatty acid and/or fatty alcohol esters other than triglycerides and plant waxes, non-silicone waxes other than fatty alcohols, and silicones, and mixtures thereof.
- the composition of the invention contains one or more oils, that is to say one or more fatty substance (s) that are liquid at room temperature (25°C) and at atmospheric pressure (760 mmHg; i.e. 1.013 ⁇ 10 5 Pa) .
- the oil (s) are chosen from linear or branched liquid hydrocarbons, of mineral or synthetic origin, containing more than 16 carbon atoms, and especially liquid petroleum jelly, hydrogenated polyisobutene, C 6 -C 16 alkanes; triglyceride oils of plant origin; liquid fatty acid and/or fatty alcohol esters; liquid fatty alcohols; and mixtures thereof.
- Particularly preferred oils are chosen from liquid fatty alcohols comprising from 8 to 20 carbon atoms.
- a most particularly preferred oil is octyldodecanol.
- the fatty substances may be present in an amount ranging from 0.05% to 10% by weight, preferably from 0.1% to 10% by weight, better still from 0.2% to 5% by weight, even better still from 0.2% to 2% by weight, relative to the total weight of the composition.
- composition according to the invention advantageously comprises water, in a content of greater than or equal to 40% by weight relative to the total weight of composition.
- the water content in the composition of the invention preferably ranges from 40% to 95% by weight, more preferentially from 40% to 80% by weight, relative to the total weight of the composition.
- composition according to the invention may also comprise one or more water-soluble organic solvents (solubility of greater than or equal to 5% in water at 25°C and at atmospheric pressure) .
- water-soluble organic solvents examples include linear or branched and preferably saturated monoalcohols or diols, comprising 2 to 10 carbon atoms, such as ethyl alcohol, isopropyl alcohol, hexylene glycol (2-methyl-2, 4-pentanediol) , neopentyl glycol and 3-methyl-1, 5-pentanediol, butylene glycol, dipropylene glycol and propylene glycol; aromatic alcohols such as phenylethyl alcohol; polyols containing more than two hydroxyl functions, such as glycerol; polyol ethers, for instance ethylene glycol monomethyl, monoethyl and monobutyl ether, propylene glycol or ethers thereof, for instance propylene glycol monomethyl ether; and also diethylene glycol alkyl ethers, especially C 1 -C 4 alkyl ethers, for instance diethylene glycol monoethyl ether or
- the water-soluble organic solvents when they are present, generally represent between 1% and 20% by weight relative to the total weight of the composition according to the invention, and preferably between 5% and 10% by weight.
- composition according to the invention preferably further comprises one or more alkaline agents.
- the alkaline agent (s) can especially be chosen from aqueous ammonia, alkali metal carbonates or bicarbonates, organic amines with a pKb at 25°C of less than 12, in particular less than 10 and even more advantageously less than 6; from the salts of the amines mentioned previously with acids such as carbonic acid or hydrochloric acid: it should be noted that it is the pKb corresponding to the function of highest basicity.
- the amines are chosen from alkanolamines, in particular comprising a primary, secondary or tertiary amine function, and one or more linear or branched C 1 -C 8 alkyl groups bearing one or more hydroxyl radicals; from oxyethylenated and/or oxypropylenated ethylenediamines, and from amino acids and compounds having the following formula:
- W is a C 1 -C 6 alkylene residue optionally substituted with a hydroxyl group or a C 1 -C 6 alkyl radical
- Rx, Ry, Rz and Rt which may be identical or different, represent a hydrogen atom or a C 1 -C 6 alkyl, C 1 -C 6 hydroxyalkyl or C 1 -C 6 aminoalkyl radical.
- the composition according to the invention comprises aqueous ammonia and/or at least one alkanolamine and/or at least one basic amino acid, more advantageously aqueous ammonia and/or at least one alkanolamine, such as monoethanolamine, or mixtures thereof.
- the content of alkaline agent (s) ranges from 0.01% to 30% by weight, preferably from 0.1% to 20% by weight and better still from 1% to 10% by weight relative to the total weight of the composition. It should be noted that this content is expressed as NH 3 when the alkaline agent is aqueous ammonia.
- the pH of composition of the invention is preferably greater than or equal to 8, preferably ranges from 8 to 12, and more preferably from 9 to 11.
- acidifying agents such as hydrochloric acid, (ortho) phosphoric acid, sulfuric acid, boric acid, and also carboxylic acids, for instance acetic acid, lactic acid or citric acid, or sulfonic acids.
- Alkaline agents such as those previously mentioned may also be used.
- composition according to the may also comprise one or more direct dyes.
- Examples of particularly suitable direct dyes include nitrobenzene dyes; azo direct dyes; azomethine direct dyes; methine direct dyes; azacarbocyanin direct dyes, for instance tetraazacarbocyanines (tetraazapentamethines) ; quinone and in particular anthraquinone, naphthoquinone or benzoquinone direct dyes; azine direct dyes; xanthene direct dyes; triarylmethane direct dyes; indoamine direct dyes; indigoid direct dyes; phthalocyanine direct dyes, porphyrin direct dyes and natural direct dyes, alone or as mixtures.
- direct dyes from among: azo; methine; carbonyl; azine; nitro (hetero) aryl; tri(hetero) arylmethane; porphyrin; phthalocyanine and natural direct dyes, alone or as mixtures.
- the direct dye (s) may represent from 0.0001% to 10% by weight and preferably from 0.005% to 5% by weight relative to the total weight of the composition.
- composition according to the invention may also comprise one or more cosmetic adjuvants.
- the composition may comprise one or more additives that are well known in the art, such as anionic, nonionic or amphoteric polymers or mixtures thereof, agents for preventing hair loss, vitamins and provitamins including panthenol, sunscreens, mineral or organic pigments, sequestrants, plasticizers, solubilizers, acidifying agents, mineral or organic thickeners, especially polymeric thickeners, opacifiers, antioxidants, hydroxy acids, nacreous agents, fragrances and preserving agents.
- additives that are well known in the art, such as anionic, nonionic or amphoteric polymers or mixtures thereof, agents for preventing hair loss, vitamins and provitamins including panthenol, sunscreens, mineral or organic pigments, sequestrants, plasticizers, solubilizers, acidifying agents, mineral or organic thickeners, especially polymeric thickeners, opacifiers, antioxidants, hydroxy acids, nacreous agents, fragrances and preserving agents.
- the above adjuvants may generally be present in an amount, for each of them, of between 0 and 20% by weight relative to the total weight of the composition.
- the composition further comprises one or more oxidizing agents.
- the composition is then said to be "ready to use”in the sense that it does not require the use of a separate oxidizing composition.
- the oxidizing agent (s) used in the context of the invention are chemical oxidizing agents other than atmospheric oxygen.
- the said oxidizing agent (s) are preferably chosen from the group formed by hydrogen peroxide, urea peroxide, alkali metal bromates or ferricyanides, peroxygenated salts, for instance persulfates, perborates, peracids and precursors thereof and alkali metal or alkaline-earth metal percarbonates, and most particularly hydrogen peroxide.
- the oxidizing agent (s) may represent from 0.01% to 20%, preferably from 0.1% to 10% and better still from 2% to 8% by weight, relative to the total weight of the composition.
- compositions according to the invention may be in the form of fluid or thickened liquids, gels or creams.
- a viscosity measured at ambient temperature and atmospheric pressure, ranging from 10 to 100 UD, preferably from 20 to 80 UD, and even more preferably from 50 to 70 UD, when using rotor 3 under 200 rpm for 30 seconds.
- the viscosity of the composition of the present invention is measured using a ProRheo R180 machine from the company Prorheo, Roter 3 is used adapted to the viscosity of the composition to be tested (rotor is chosen for having a measure between 10 and 100 for UD Unit Deviation) , the measure being made after 30 seconds rotating the rotor inside the composition, with a shear rate from 200s -1 .
- the invention also relates to the use of the composition as described above for dyeing keratin fibres, in particular the hair.
- Another subject of the invention is a process for dyeing human keratin fibres, in particular the hair, using the composition as described above.
- the composition is "ready to use", i.e. it already contains at least one oxidizing agent.
- the dyeing process of the invention consists in applying the "ready-to-use"composition to the keratin fibres.
- the dyeing process of the invention consists in applying the composition as described above to the keratin fibres, the said composition being applied with a separate oxidizing composition.
- the oxidizing composition that is used in this embodiment of the process of the invention comprises one or more oxidizing agents.
- the oxidizing agent (s) of the oxidizing composition are as defined above, ie, they are preferably chosen from the group formed by hydrogen peroxide, urea peroxide, alkali metal bromates or ferricyanides, peroxygenated salts, for instance persulfates, perborates, peracids and precursors thereof and alkali metal or alkaline-earth metal percarbonates, and most particularly hydrogen peroxide.
- the oxidizing agent (s) may represent from 0.01% to 20%, preferably from 0.1% to 10% and better still from 2% to 8%by weight, relative to the total weight of the oxidizing composition.
- the composition according to the invention is mixed at the time of use with the oxidizing composition as described above.
- composition of the present invention is intended to mean the action of putting the composition of the present invention into a container or palm, together with the oxidizing composition as described above, with or without stirring them.
- the composition of the present invention is put into a container or palm together with the oxidizing composition as described above, without stirring them.
- composition of the invention due to the very good foaming properties of the composition of the invention, it is particularly advantageous and convenient to apply onto the keratin fibers the composition of the invention and an oxidizing composition without the need of stirring them in a container or palm, but apply them directly on the hair, and allow the mixture thus formed onto the hair to foam for example by massaging with the fingers.
- compositions described previously, optionally mixed beforehand, are applied to wet or dry keratin fibres.
- composition (s) are usually left in place on the fibres for a time generally ranging from 1 minute to 1 hour and preferably from 5 minutes to 30 minutes.
- the temperature during the process is conventionally between 20 and 80°C and preferably between 20 and 60°C.
- the human keratin fibres are advantageously rinsed with water. They may optionally be further washed with a shampoo, followed by rinsing with water, before being dried or left to dry.
- the process may be repeated several times in order to obtain the desired coloration.
- Another subj ect of the invention concerns a multi-compartment device, or a kit for dyeing keratin fibres, comprising at least two compartments:
- the kit also comprises an additional compartment containing an additional composition comprising one or more treating agents.
- compositions of the kit are packaged in separate compartments, which may be optionally accompanied by suitable identical or different application means, such as fine brushes, coarse brushes or sponges.
- kit may also be equipped with means allowing the delivery to the hair of the desired mixture, such as, for example, the device described in patent FR 2 586 913.
- the dyeing compositions hereunder were prepared, from the ingredients indicated in the table below (in which the contents are indicated in grams of active material with regard to the total weight of the composition) :
- composition C4 corresponds to the invention, whereascompositions C 1 to C3 correspond to comparative compositions.
- compositions above were tested with regard to thefollowing properties:
- Stability on storage of the composition was performed by leaving the compositions C 1 to C4 at 4°C, roomtemperature (25°C) , and 45°C for 2 months. Then C 1 to C4 were leftunder 37°C for 6 months to evaluate the long term stabilities.
- Viscosity of the composition The viscosities of the compositions C1 to C4 were measured at 25°C, using a ProRheo R180 machine from the company Prorheo, Roter 3 was used adapted to the viscosity of the product to be tested (rotor is chosen for having a measure between 10 and 100 for UD Unit Deviation) , the measure being made after 30 seconds rotating the rotor inside the composition, with a shear rate from 200s -1 .
- Ease of application onto the keratin fibers The ease of application onto hair of the compositions C1 to C4 was measured by 3 hair dressers using the compositions C1 to C4 for dyeing the hair. 30g of the compositions C1 to C4 were poured in the palm of the hair dressers, respectively, together with same amount of an oxidizer containing 6% of hydrogen peroxide. Without mixing, the hair dressers applied the products (compositions C1 to C4 mixing with oxidizers) immediately onto the middle-length hair, i.e., hair length is at the shoulder. The hair were massaged and foam was formed. After 15 minutes, the hair with the products mentioned above were rinsed with water.
- a dyeing composition in accordance with the invention was prepared, from the ingredients indicated in the table below (in which the contents are indicated in grams of active material with regard to the total weight of the composition) :
- Composition A 4-diaminophenoxyethanol, HCl 0.60 Resorcinol 1.70 m-aminophenol 0.2 p-phenylenediamine 2 Sodium laureth sulfate (2 OE) 10.0 Cocoylbetaine 3.0 Cocamide mono-isopropanolamine 0.3 Polyquaternium-10 0.8 PEG-120 methyl glucose dioleate 0.1 Polysorbate 21 0.2 Octyldodecanol 0.40 Ethanolamine 2.40 Glycerin 5 Ascorbic acid 0.25 Sodium metabisulfite 0.7 EDTA 0.1 Fragrance qs Water qs 100 g
- composition prepared above was poured in a palm together with 30g of an oxidizer containing 6% of hydrogen peroxide. Without mixing, the compositions were applied immediately onto the middle-length hair, i.e., hair length is at the shoulder. The hair was massaged and foam was formed. After 15 minutes, the hair was rinsed with water.
- the viscosity of the composition mentioned above is 63.8 UD, using the measurement method disclosed in example 1 above. It allows the composition staying in the palm without floating away. And furthermore, when mixing with the oxidizer on the hair, it allows the mixture and the foam staying on the hair without dropping or flying.
- the turbidity of the composition mentioned above is 6 NTU, using the measurement method disclosed in the above description.
- composition mentioned above is stable over 2 months under 4°C, room temperature, and 45°C.
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Abstract
Description
Properties | C1 | C2 | C3 | C4 |
Viscosity | 3 | 1 | 1 | 4 |
Stability | 1 | 1 | 1 | 4 |
Application | 4 | 1 | 1 | 5 |
Composition | A |
2, 4-diaminophenoxyethanol, HCl | 0.60 |
Resorcinol | 1.70 |
m-aminophenol | 0.2 |
p-phenylenediamine | 2 |
Sodium laureth sulfate (2 OE) | 10.0 |
Cocoylbetaine | 3.0 |
Cocamide mono-isopropanolamine | 0.3 |
Polyquaternium-10 | 0.8 |
PEG-120 methyl glucose dioleate | 0.1 |
Polysorbate 21 | 0.2 |
Octyldodecanol | 0.40 |
Ethanolamine | 2.40 |
Glycerin | 5 |
Ascorbic acid | 0.25 |
Sodium metabisulfite | 0.7 |
EDTA | 0.1 |
Fragrance | qs |
Water | qs 100 g |
Claims (21)
- Cosmetic composition for the oxidation dyeing of keratin fibres comprising:a) one or more oxidation dye (s) ,b) one or more cationic polymer (s) ,c) one or more amphoteric or zwitterionic surfactant (s) ,d) one or more non ionic surfactant (s) chosen from alkanolamides of C6-C30 fatty acids, ande) one or more anionic surfactant (s) , in an amount of at least 1.5%by weight, with regard to the total weight of the composition.
- Composition according to Claim 1, characterized in that the oxidation dye (s) comprise one or more oxidation bases, preferably chosen from para-phenylenediamines, bis (phenyl) alkylenediamines, para-aminophenols, ortho-aminophenols, heterocyclic bases, and the addition salts thereof, and mixtures thereof.
- Composition according to the preceding claim, characterized in that the oxidation base (s) represent from 0.0001%to 10%by weight, preferably from 0.005%to 5%by weight and better still from 0.1%to 5%by weight relative to the total weight of the composition.
- Composition according to any one of the preceding claims, characterized in that the oxidation dye (s) comprise one or more couplers, preferably chosen from meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers, heterocyclic couplers, and the addition salts thereof, and mixtures thereof.
- Composition according to the preceding claim, characterized in that the said coupler (s) represent from 0.0001%to 10%by weight, preferably from 0.005%to 5%by weight, relative to the total weight of the composition.
- Composition according to any one of the preceding claims, characterized in that the cationic polymers are chosen from:(1) homopolymers or copolymers derived from acrylic or methacrylic esters or amides and comprising at least one of the units of the following formulae:in which:-R3, which may be identical or different, denote a hydrogen atom or a CH3 group;-A, which may be identical or different, represent a linear or branched divalent alkyl group of 1 to 6 carbon atoms, preferably 2 or 3 carbon atoms, or a hydroxyalkyl group of 1 to 4 carbon atoms;-R4, R5 and R6, which may be identical or different, represent an alkyl group containing from 1 to 18 carbon atoms or a benzyl group, and preferably an alkyl group containing from 1 to 6 carbon atoms;-R1 and R2, which may be identical or different, represent a hydrogen atom 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;(2) Cationic polysaccharides, in particular cationic celluloses and cationic galactomannan gums;(3) Polymers composed of piperazinyl units and of divalent alkylene or hydroxyalkylene groups containing linear or branched chains, optionally interrupted by oxygen, sulfur or nitrogen atoms or by aromatic or heterocyclic rings, and also the oxidation and/or quaternization products of these polymers;(4) Water-soluble polyaminoamides prepared in particular by polycondensation of an acidic compound with a polyamine; these polyaminoamides being optionally crosslinked by an epihalohydrin, a diepoxide, a dianhydride, an unsaturated dianhydride, a bisunsaturated derivative, a bishalohydrin, a bisazetidinium, a bishaloacyldiamine or an alkyl bishalide or alternatively by an oligomer resulting from the reaction of a bifunctional compound reactive with respect to a bishalohydrin, a bisazetidinium, a bishaloacyldiamine, an alkyl bishalide, an epihalohydrin, a diepoxide or a bisunsaturated derivative; these polyaminoamides being optionally alkylated or, if they comprise one or more tertiary amine functions, quaternized;(5) Polyaminoamide derivatives resulting from the condensation of polyalkylene polyamines with polycarboxylic acids followed by alkylation with difunctional agents;(6) Polymers obtained by reaction of a polyalkylenepolyamine comprising two primary amine groups and at least one secondary amine group with a dicarboxylic acid chosen from diglycolic acid and saturated aliphatic dicarboxylic acids having from 3 to 8 carbon atoms; the molar ratio of polyalkylenepolyamine to dicarboxylic acid preferably being of between 0.8: 1 and 1.4: 1; the polyaminoamide resulting therefrom being reacted with epichlorohydrin in a molar ratio of epichlorohydrin in relation to the secondary amine group of the polyaminoamide preferably of between 0.5: 1 and 1.8: 1;(7) Cyclopolymers of alkyldiallylamine or of dialkyldiallylammonium, such as the homopolymers or copolymers comprising, as main constituent of the chain, units corresponding to formula (PI) or (PII) :in which:-k and t are equal to 0 or 1, the sum k + t being equal to 1;-R12 denotes a hydrogen atom or a methyl group;-R10 and R11, independently of each other, denote an alkyl group containing from 1 to 6 carbon atoms, a hydroxyalkyl group in which the alkyl group contains 1 to 5 carbon atoms, a C1-C4 amidoalkyl group; or alternatively R10 and R11 may denote, together with the nitrogen atom to which they are attached, heterocyclic groups such as piperidyl or morpholinyl; R10 and R11, independently of each other, preferably denote an alkyl group containing from 1 to 4 carbon atoms;-Y- is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulfate, bisulfite, sulfate or phosphate;(8) quaternary diammonium polymers comprising repeating units of formula:in which:-R13, R14, R15 and R16, which may be identical or different, represent aliphatic, alicyclic or arylaliphatic groups comprising from 1 to 20 carbon atoms or C1-4 hydroxyalkylaliphatic groups, or else R13, R14, R15 and R16, together or separately, form, with the nitrogen atoms to which they are attached, heterocycles optionally comprising a second heteroatom other than nitrogen, or else R13, R14, R15 and R16 represent a linear or branched C1-C6 alkyl group sub stituted by a nitrile, ester, acyl, amide or -CO-O-R17-D or -CO-NH-R17-D group, where R17 is an alkylene and D a quaternary ammonium group;-A1 and B1 represent divalent polymethylene groups comprising from 2 to 20 carbon atoms which may be linear or branched, and saturated or unsaturated, and which may contain, linked to or inserted 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;it being understood that A1, R13 and R15 can form, with the two nitrogen atoms to which they are attached, a piperazine ring;(9) Polyquaternary ammonium polymers comprising units of formula (PV) :in which:-R18, R19, R20 and R21, which may be identical or different, represent a hydrogen atom or a methyl, ethyl, propyl, β-hydroxyethyl, β-hydroxypropyl or -CH2CH2 (OCH2CH2) pOH group, where p is equal to 0 or to an integer of between 1 and 6, with the proviso that R18, R19, R20 and R21 do not simultaneously represent a hydrogen atom,-r and s, which may be identical or different, are integers between 1 and 6,-q is equal to 0 or to an integer between 1 and 34,-X- denotes an anion such as a halide,-A denotes a radical of a dihalide or preferably represents -CH2-CH2-O-CH2-CH2-;(10) Quaternary polymers of vinylpyrrolidone and of vinylimidazole;(11) Polyamines;(12) Polymers comprising in their structure:(a) one or more units corresponding to formula (A) below:(b) optionally one or more units corresponding to formula (B) below:and preferably the cationic polymer (s) are chosen from those of family (2) mentioned above.
- Composition according to the preceding claim, characterized in that the cationic polymer (s) are chosen from quaternized hydroxyalkylcelluloses, more preferably from quaternized hydroxyethylcelluloses and even more preferably from hydroxyethyl cellulose-2-hydroxypropyl trimethyl ammonium chloride ether.
- Composition according to any one of the preceding claims, characterized in that it contains from 0.1 to 5%by weight of cationic polymer (s) , more preferably from 0.2 to 2.5%by weight, with regard to the total weight of the composition.
- Composition according to any one of the preceding claims, characterized in that the amphoteric or zwitterionic surfactant (s) are chosen from (C8-C20) alkylbetaines, (C8-C20) alkylsulfobetaines, (C8-C20) alkylamido (C3-C8) alkylbetaines and (C8-C20) alkylamido (C6-C8)alkylsulfobetaines, more preferably from (C8-C20) alkylbetaines and even more preferably the composition comprises cocoylbetaine.
- Composition according to any one of the preceding claims, characterized in that said amphoteric or zwitterionic surfactant (s) are present in an amount of from 0.01 to 15%by weight, preferably from 0.1 to 10%by weight, and more preferably from 1 to 5%by weight, based on the total weight of the composition.
- Composition according to any one of the preceding claims, characterized in that said non ionic surfactant (s) are chosen from mono-alkanolamides and di-alcanolamides of C8-C30 fatty acids, preferably from mono-alkanolamides and di-alcanolamides of C8-C18 fatty acids and even more preferably the composition comprises cocamide mono-isopropanolamine.
- Composition according to any one of the preceding claims, characterized in that it comprises said non ionic surfactant (s) chosen from alkanolamides of C6-C30 fatty acids in an amount ranging from 0.05 to 5 %by weight, preferably from 0.1 to 1 %by weight, with regard to the total weight of the composition.
- Composition according to any one of the preceding claims, characterized in that said anionic surfactants are chosen from (C6-C30) alkyl sulfates, (C6-C30) alkyl ether sulfates, (C6-C30) alkylamido ether sulfates, alkylaryl polyether sulfates and monoglyceride sulphates, all these compounds optionally comprising from 1 to 20 ethylene oxide units; and more preferably from (C12-C20) alkyl sulphates and (C12-C20) alkyl ether sulfates comprising from 2 to 20 ethylene oxide units, and even more preferably from 1 to 4 ethylene oxide units, especially in the form of alkali metal, ammonium, amino alcohol and alkaline-earth metal salts, or a mixture of these compounds.
- Composition according to any one of the preceding claims, characterized in that it comprises said anionic surfactant (s) in an amount of at least 3%by weight, and preferably in an amount ranging from 5 to 30%by weight, more preferably from 5 to 15%by weight, with regard to the total weight of the composition.
- Composition according to any one of the preceding claims, characterized in that it further comprises one or more fatty substances preferably chosen from oils, and more preferably chosen from liquid fatty alcohols comprising from 8 to 20 carbon atoms, and even more preferably the composition comprises octyldodecanol.
- Composition according to the preceding claim, characterized in that it contains said fatty substance (s) in an amount ranging from 0.05%to 10%by weight, preferably from 0.1%to 10%by weight, better still from 0.2%to 5%by weight, even better still from 0.2%to 2%by weight, relative to the total weight of the composition.
- Composition according to any one of the preceding claims, characterized in that it further comprises one or more oxidizing agents, preferably chosen from the group formed by hydrogen peroxide, urea peroxide, alkali metal bromates or ferricyanides, peroxygenated salts, for instance persulfates, perborates, peracids and precursors thereof and alkali metal or alkaline-earth metal percarbonates, and more preferably hydrogen peroxide.
- Process for dyeing human keratin fibres, in particular the hair, wherein the composition as defined in claim 17 is applied onto said keratin fibres.
- Process for dyeing human keratin fibres, in particular the hair, wherein a composition as defined in anyone of claims 1 to 16 is applied onto said keratin fibres sequentially to or simultaneously with a separate oxidizing composition comprising one or more oxidizing agents preferably chosen from the group formed by hydrogen peroxide, urea peroxide, alkali metal bromates or ferricyanides, peroxygenated salts, for instance persulfates, perborates, peracids and precursors thereof and alkali metal or alkaline-earth metal percarbonates, and most particularly hydrogen peroxide.
- The process of the preceding claim, wherein the composition as defined in anyone of claims 1 to 16 is applied to the keratin fibres with an oxidizing composition, preferably without stirring them.
- Kit for the oxidation dyeing keratin fibres, comprising at least two compartments:-a first compartment containing a dyeing composition as defined in anyone of claims 1 to 16; and-a second compartment containing an oxidizing composition as defined in claim 19.
Priority Applications (4)
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MX2017009500A MX2017009500A (en) | 2015-01-20 | 2015-01-20 | Cosmetic composition for the oxidation dyeing of keratin fibres comprising a cationic polymer and a particular combination of surfactants. |
PCT/CN2015/071080 WO2016115674A1 (en) | 2015-01-20 | 2015-01-20 | Cosmetic composition for the oxidation dyeing of keratin fibres comprising a cationic polymer and a particular combination of surfactants |
CN201580078087.7A CN107427426A (en) | 2015-01-20 | 2015-01-20 | The cosmetic composition of the oxidising dyeing for keratin fiber of particular combination comprising cationic polymer and surfactant |
BR112017015526-5A BR112017015526B1 (en) | 2015-01-20 | 2015-01-20 | cosmetic composition for the oxidation dyeing of keratin fibers, process for the dyeing of human keratin fibers and kit for the oxidation dyeing of keratin fibers |
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PCT/CN2015/071080 WO2016115674A1 (en) | 2015-01-20 | 2015-01-20 | Cosmetic composition for the oxidation dyeing of keratin fibres comprising a cationic polymer and a particular combination of surfactants |
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CN (1) | CN107427426A (en) |
BR (1) | BR112017015526B1 (en) |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018056235A1 (en) * | 2016-09-20 | 2018-03-29 | L'oreal | Composition for keratin fibers |
WO2021124348A1 (en) * | 2019-12-20 | 2021-06-24 | L'ORéAL S.A. | Multiple-compartment device comprising at least one internal frangible seal containing a keratin fibers dyeing composition |
FR3146068A1 (en) * | 2023-02-27 | 2024-08-30 | L'oreal | DYE COMPOSITION FOR DYEING KERATIN FIBERS AND DYEING KIT CONTAINING THE SAME |
US12144878B2 (en) | 2019-12-20 | 2024-11-19 | L'oreal | Multiple-compartment device comprising at least one internal frangible seal containing a keratin fibers dyeing composition |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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FR3082739B1 (en) * | 2018-06-20 | 2020-05-29 | L'oreal | HAIR COLORING PROCESS USING A COLORING COMPOSITION AND AN OXIDIZING COMPOSITION, SAID COMPOSITIONS COMPRISING A SCLEROGLUCAN GUM. |
CN113646479B (en) * | 2019-01-17 | 2023-06-13 | 埃斯普投资有限公司 | Method for strengthening non-keratin fibers and use thereof |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US20020157191A1 (en) * | 2001-02-23 | 2002-10-31 | Stephen Casperson | Two-part aqueous composition for oxidative coloration of hair |
EP1905421A1 (en) * | 2006-09-29 | 2008-04-02 | Kao Corporation | Hair dye composition |
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TWI422394B (en) * | 2007-10-24 | 2014-01-11 | Kao Corp | Two-part hair dye |
BR112015002202B1 (en) * | 2012-08-02 | 2019-10-22 | Oreal | keratin fiber dyeing composition, keratin fiber dyeing process and device |
-
2015
- 2015-01-20 MX MX2017009500A patent/MX2017009500A/en active IP Right Grant
- 2015-01-20 CN CN201580078087.7A patent/CN107427426A/en active Pending
- 2015-01-20 WO PCT/CN2015/071080 patent/WO2016115674A1/en active Application Filing
- 2015-01-20 BR BR112017015526-5A patent/BR112017015526B1/en active IP Right Grant
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020157191A1 (en) * | 2001-02-23 | 2002-10-31 | Stephen Casperson | Two-part aqueous composition for oxidative coloration of hair |
EP1905421A1 (en) * | 2006-09-29 | 2008-04-02 | Kao Corporation | Hair dye composition |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018056235A1 (en) * | 2016-09-20 | 2018-03-29 | L'oreal | Composition for keratin fibers |
WO2021124348A1 (en) * | 2019-12-20 | 2021-06-24 | L'ORéAL S.A. | Multiple-compartment device comprising at least one internal frangible seal containing a keratin fibers dyeing composition |
US12144878B2 (en) | 2019-12-20 | 2024-11-19 | L'oreal | Multiple-compartment device comprising at least one internal frangible seal containing a keratin fibers dyeing composition |
FR3146068A1 (en) * | 2023-02-27 | 2024-08-30 | L'oreal | DYE COMPOSITION FOR DYEING KERATIN FIBERS AND DYEING KIT CONTAINING THE SAME |
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MX2017009500A (en) | 2018-02-09 |
BR112017015526B1 (en) | 2021-06-08 |
CN107427426A (en) | 2017-12-01 |
BR112017015526A2 (en) | 2019-11-19 |
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