WO2010133805A1 - Dyeing composition containing a secondary para-phenylenediamine oxidation base and a pearling agent - Google Patents
Dyeing composition containing a secondary para-phenylenediamine oxidation base and a pearling agent Download PDFInfo
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- WO2010133805A1 WO2010133805A1 PCT/FR2010/050966 FR2010050966W WO2010133805A1 WO 2010133805 A1 WO2010133805 A1 WO 2010133805A1 FR 2010050966 W FR2010050966 W FR 2010050966W WO 2010133805 A1 WO2010133805 A1 WO 2010133805A1
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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
- A61K8/41—Amines
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
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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
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
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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
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/26—Aluminium; Compounds 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
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/29—Titanium; Compounds 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
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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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/342—Alcohols having more than seven atoms in an unbroken chain
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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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
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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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
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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
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
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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
- A61K8/738—Cyclodextrins
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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
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/26—Optical properties
Definitions
- the invention relates to a dye composition comprising at least one particular para-phenylenediamine oxidation base and at least one pearlescent agent.
- the invention also relates to a process for dyeing keratinous fibers, in particular human fibers such as the hair, using this composition, as well as devices with several appropriate compartments.
- oxidation bases such as ortho or para-phenylenediamines, ortho or para-aminophenols and heterocyclic compounds.
- oxidation bases are colorless or weakly colored compounds which, when combined with oxidizing products, can give rise to colored compounds by a process of oxidative condensation.
- oxidation bases can be varied by combining them with couplers or color modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as than indolic compounds.
- couplers or color modifiers the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as than indolic compounds.
- couplers or color modifiers the variety of molecules involved in oxidation bases and couplers, allows to obtain a rich palette of colors.
- the dyes must also make it possible to cover the white hair, and finally be the least selective possible, that is to say, to obtain the lowest possible color differences throughout the same keratin fiber, which is in general differently sensitized (ie damaged) between its point and its root.
- oxidation bases of the para-phenylene diamine secondary type of formula (I) below for dyeing keratinous fibers, especially the hair.
- a base is disclosed in EP1580184 and EP0055386.
- This base has the drawbacks of leading to insufficiently intense or chromatic and / or too selective staining.
- the object of the present invention is to obtain a composition for hair dyeing which has improved dyeing properties in terms of intensity or chromaticity, and / or selectivity and / or resistance to external agents.
- oxidation bases selected from the compound of formula (I) or its addition salts with an acid
- the invention also relates to a dyeing process using this composition.
- It also relates to a multi-compartment device comprising in one of them, the dye composition according to the invention without oxidant, and in another, a composition comprising one or more oxidizing agents.
- the device comprises a first compartment containing one or more oxidation bases chosen from the compound of formula (I) or its salts with an acid and optionally one or more different oxidation bases of the compound of formula (I) or its salts and optionally one or more couplers; a second compartment containing a composition comprising one or more pearlescent agents and optionally a third compartment containing a composition comprising one or more oxidizing agents
- composition of the present invention makes it possible in particular to obtain a keratinous fiber coloring composition which is suitable for use in oxidation dyeing and makes it possible to obtain a coloring with varied shades, intense or chromatic, aesthetic, not very selective and resistant. well to the various aggressions that can undergo the hair such as the shampoos, the sweat and the permanent deformations and the light.
- the compound of formula (I) may be in the form of addition salts chosen especially from acid addition salts such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
- the compound of formula (I) or its salts are generally present each in an amount of between 0.001 to 10% by weight relative to the total weight of the dye composition, preferably between 0.005 and 6% by weight.
- the dye composition of the invention may optionally comprise one or more additional oxidation bases conventionally used for dyeing keratinous fibers, different from the compound of formula (I) or its salts.
- these additional oxidation bases are chosen from the different para-phenylenediamines of the compound of formula (I) and of its addition salts, bisphenylalkylenediamines, para-aminophenols, bis-para-amines and aminophenols, ortho-aminophenols, heterocyclic bases.
- para-phenylenediamines there may be mentioned by way of example, para-phenylenediamine, para-toluenediamine, 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- methyl aniline, 4-N, N-bis- ( ⁇ -hydroxyethyl) amino-2-
- para-phenylenediamine para-toluenediamine, 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, 2- ⁇ -acetylaminoethyloxy para-phenylenediamine, and their addition salts with an acid are particularly preferred.
- N N'-bis- ( ⁇ -hydroxyethyl) N
- N'-bis (4'-aminophenyl) -1,3-diamino propanol, N may be mentioned by way of example.
- para-aminophenols examples include para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluoro phenol, 4-amino-3-hydroxymethylphenol, 4- amino 2-methyl phenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- ( ⁇ -hydroxyethylaminomethyl) phenol, 4- amino 2-fluoro phenol, 1-hydroxy-4-methylamino-benzene, 2-2'-methylenebis-4-amino phenol and their addition salts with an acid.
- ortho-aminophenols there may be mentioned by way of example, 2-amino phenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol, 5-acetamido-2-amino phenol, and their addition salts with an acid.
- heterocyclic bases that may be mentioned by way of example are pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
- pyridine derivatives mention may be made of the compounds described for example in patents GB 1 026 978 and GB 1 153 196, such as 2,5-diaminopyridine, 2- (4-methoxyphenyl) amino 3-amino pyridine, 2,3-diamino-6-methoxy pyridine, 2- ( ⁇ -methoxyethyl) amino-3-amino-6-methoxy pyridine, 3,4-diamino pyridine, and their addition salts with an acid.
- pyrimidine derivatives mention may be made of the compounds described, for example, in 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, , 4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine, and pyrazolopyrimidine derivatives such as those mentioned in patent application FR-A-2750048 and among which mention may be made of pyrazolo [1, 5-a] -pyrimidine-3,7-diamine; 2,5-dimethyl pyrazolo [1,5-a] pyrimidine-3,7-diamine; pyrazolo [1,5-a] pyrimidine-3,5-diamine; 2,7-dimethyl pyrazolo
- pyrazole derivatives mention may be made of the compounds described in DE 3843892, DE 4133957 and patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988 as the 4.5 1-methyl pyrazole, 4,5-diamino-1- ( ⁇ -hydroxyethyl) pyrazole, 3,4-diamino pyrazole, 4,5-diamino-1- (4'-chlorobenzyl) pyrazole, 4,5 1-diamino-1,3-dimethyl pyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydrazino pyrazole 1-Benzyl-4,5-diamino-3-methyl-pyrazole, 4,5-diamino-3-tert-buty
- diaminopyrazolinones described in patent application FR2886137 and in particular 2,3-diamino-6,7-dihydro-1H, 5H-pyrazol-1-one and its salts.
- addition salts of the oxidation bases and couplers that can be used in the context of the invention are chosen especially from the addition salts with an acid such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates and addition salts with a base such as sodium hydroxide, potassium hydroxide, ammonia, amines or alkanolamines.
- an acid such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates
- a base such as sodium hydroxide, potassium hydroxide, ammonia, amines or alkanolamines.
- composition comprises one or more additional oxidation bases, that (s) represents (s) more particularly from 0.0005 to 12% by weight relative to the total weight of the dyeing composition, preferably from 0.005 to 8 % in weight.
- the dye composition according to the invention may also optionally comprise one or more couplers conventionally used for dyeing keratinous fibers.
- couplers there may be mentioned meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalenic couplers, heterocyclic couplers and their addition salts.
- a coupler there may be mentioned 2-methyl-5-aminophenol, 5-N- ( ⁇ -hydroxyethyl) amino-2-methylphenol, 6-chloro-2-methyl-5-aminophenol, 3 amino phenol, 2,4-dichloro-3-aminophenol, 5-amino-4-chloro-o-cresol, 1,3-dihydroxy benzene, 1,3-dihydroxy-2-methyl benzene, 4- chloro 1,3-dihydroxy benzene, 2,4-diamino 1- ( ⁇ -hydroxyethyloxy) benzene, 2-amino 4- ( ⁇ -hydroxyethylamino) -1-methoxybenzene, 1,3-diamino benzene, 1,3 bis-(2,4-diaminophenoxy) propane, 3-ureido aniline, 3-ureido 1-dimethylamino benzene, sesamol, 1- ⁇ -hydroxyethylamino- 3,4-methylenedi
- the coupler (s), if present, generally represent an amount of between 0.001% and 10% by weight relative to the total weight of the dyeing composition, preferably between 0.005% and 6% by weight. weight.
- the dye composition in accordance with the invention may also contain one or more direct dyes that may be chosen in particular from nitro dyes of the benzene series, azo direct dyes and methine direct dyes. These direct dyes may be nonionic, anionic or cationic in nature.
- the direct dye (s), if present, generally represent an amount of between 0.001% and 20% by weight relative to the total weight of the dyeing composition, preferably between 0.01% and 10% by weight.
- the dye composition according to the invention comprises one or more pearlescent agents.
- pearlescent agent in the sense of the present invention any compound capable of imparting to the composition of the invention an iridescent, iridescent, moiré or metallized appearance or effect.
- the pearling agents used in the composition according to the invention are chosen from the following compounds, alone or in mixtures: a) polyol esters having at least two carbon atoms and long chain fatty acids, more particularly Ci 0 -C 3 O and preferably C16-C22; such as mono or diesters of polyols and fatty acids; preferably the polyols are ethylene glycol and the polyalkylene glycol having from 2 to 10 ethylene oxide units; b) esters of long chain monohydric alcohols (Ci 0 -C 30 ) such as cetyl palmitate; c) ethers of long-chain fatty alcohols, solid at a temperature of less than or equal to about 30 ° C., such as, for example, the dialkyl ethers of formula (II):
- ROR '(II) in which R and R', which may be identical or different, denote a linear or branched, saturated or unsaturated alkyl radical containing from 10 to 30 carbon atoms and preferably from 14 to 24 carbon atoms, R and R 'being chosen such that the compound of formula (II) is solid at a temperature of less than or equal to approximately 30 ° C. More particularly, R and R 'denote a stearyl radical.
- R and R ' denote a stearyl radical.
- a distearyl ether which can be used in the context of the present invention is marketed under the name CUTINA STE by the company HENKEL; d) the long chain (C 10 -C 30) esters of long chain alkanolamides (C 10 -C 30) such as distearate stearamide diethanolamide or stearate stearamide monoethanolamide; e) single-chain fatty alcohols having at least 20 carbon atoms such as behenic alcohol; and f) compounds having from 27 to 48 carbon atoms and having one or two ether and / or thioether or sulfoxide groups, and more particularly, corresponding to formula (III):
- Y denotes an oxygen atom, a sulfur atom, a sulphoxide or methylene group
- R 3 and R b has a value ranging from 24 to 44 and preferably from 28 to 40 inclusive; when X or Y denotes a sulphoxide group, X or Y denotes a sulfur atom.
- the compounds of formula (III) preferably used in accordance with the invention are those for which X denotes an oxygen atom, Y denotes a methylene group, and R 3 and R b denote radicals having 12 to 22 carbon atoms.
- these compounds may be prepared according to patent EP457688; g) coated or uncoated titanium oxides, micas and mixtures of mica and metal oxide (titanium, iron) and / or dyes, for example the products Colorona Russet, Cloisonne Orange, Cloisonne Rouge Flambe, Cloisonne Copper, Cloisonne GoId, Colorona Red GoId, Colorona Bright GoId, Timiron MP 25 GoId Plus Cosmetic, Timica GoId Sparkle, (mica-titanium oxide-brown iron oxide mixtures); Timiron Super Silver, Prestige Pearlescent Pigments, Timiron Super Violet Cosmetic, Timiron MP-10 Pearl Flake, Timiron Super GoId, Flamenco Sparkle Blue, (mica-titanium oxide blends); Color
- the pearlescent agents are preferably chosen from ethylene glycol mono- or distearate; distearyl ether; behenic alcohol; titanium oxide; micas; the mixtures of mica and metal oxide (titanium, iron) and / or dyes and 1 - (hexadecyloxy) -2-octadecanol; ⁇ -cyclodextrin or mixtures thereof.
- the composition according to the invention has a nacreous agent (s) content ranging from 0.05 to 10% by weight relative to the weight of the dye composition, and preferably from 0.1 to 5% by weight.
- the medium which is suitable for dyeing also known as a dyeing medium, generally comprises water or a mixture of water and one or more solvents such as, for example, lower alkanols in dC 4 , such as ethanol and isopropanol, polyols such as propylene glycol, dipropylene glycol or glycerol, and polyol ethers such as dipropylene glycol monomethyl ether.
- solvents such as, for example, lower alkanols in dC 4 , such as ethanol and isopropanol
- polyols such as propylene glycol, dipropylene glycol or glycerol
- polyol ethers such as dipropylene glycol monomethyl ether.
- the solvent or solvents are generally present in proportions which can be between 1 and 40% by weight approximately relative to the total weight of the dye composition, and even more preferably between 3 and 30% by weight approximately.
- the dyeing composition in accordance with the invention may also contain various adjuvants conventionally used in compositions for dyeing hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants, or mixtures thereof, anionic, cationic polymers, nonionic, amphoteric, zwitterionic or mixtures thereof, inorganic or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrating agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as, for example, volatile or non-volatile silicones, modified or unmodified, film-forming agents, ceramides, preserving agents ,.
- the adjuvants above are generally present in an amount for each of them between 0.01 and 20% by weight relative to the weight of the composition.
- the pH of the dye composition according to the invention is generally between 3 and 12 approximately, and preferably between 5 and 1 1 approximately. It can be adjusted to the desired value by means of acidifying or alkalizing agents usually used for dyeing keratin fibers or else using conventional buffer systems.
- acidifying agents mention may be made, by way of example, of mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulphonic acids.
- alkalinizing agents for example, ammonia, alkali carbonates, alkali silicates and metasilicates, alkanolamines such as mono-, di- and triethanolamines and their derivatives, sodium hydroxides, potassium or magnesium, the alkaline salts of pyrrolidine carboxylate and the compounds of formula (IV) below:
- R 3 , Rb, Rc and R d which may be identical or different, represent a hydrogen atom, a C 1 -C 4 alkyl or dC 4 hydroxyalkyl radical.
- the composition according to the invention may comprise one or more oxidizing agents.
- the oxidizing agents are those conventionally used for the oxidation dyeing of keratin fibers, for example hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulfates, peracids and the like.
- oxidase enzymes among which mention may be made of peroxidases, 2-electron oxidoreductases such as uricases and 4-electron oxygenases such as laccases. Hydrogen peroxide is particularly preferred.
- the dye composition according to the invention may be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratinous fibers, and especially human hair. It can result from mixing at the time of use of several compositions.
- compositions in a first variant, it results from the mixture of at least two compositions, one comprising one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid, optionally one or more bases.
- compositions one comprising one or more oxidation bases selected from the compound of formula (I) or its addition salts with an acid, the pearlescent agent (s), optionally one or more different additional oxidation bases of the compound of formula (I) or of its salts, and optionally one or more couplers, another composition comprising one or more oxidizing agents as described above.
- composition of the invention is therefore applied to the hair for dyeing keratinous fibers either as such or in the presence of one or more oxidizing agents, for dyeing keratinous fibers.
- the process of the present invention is a process in which the non-oxidizing composition according to the present invention as defined above, either alone or in the presence of one or more oxidizing agents, is applied to the fibers.
- the color may be revealed at acidic, neutral or alkaline pH
- the oxidizing agent (s) if present, may be added to the composition of the invention just at the time of use or may be using an oxidizing composition containing them, applied simultaneously or sequentially to the composition of the invention,
- the composition according to the present invention free of oxidizing agent (s) is mixed, preferably at the time of use, with a composition comprising, in a medium suitable for dyeing, one or more oxidizing agents.
- the mixture obtained is then applied to the keratinous fibers.
- the oxidizing agents are those indicated above. Whether with or without an oxidant, the pause time of the composition (s) varies from approximately 3 to 50 minutes, preferably from 5 to approximately 30 minutes.
- the temperature during the application is conventionally between room temperature (between 15 and 25 ° C.) and 80 ° C., preferably between room temperature and 60 ° C.
- the keratinous fibers are rinsed with water, optionally washed with shampoo, rinsed with water again and then dried.
- the oxidizing composition may also contain various adjuvants conventionally used in compositions for dyeing hair and as defined above.
- the pH of the oxidizing composition containing the oxidizing agent is such that, after mixing with the dyeing composition, the pH of the resulting composition applied to the keratinous fibers preferably varies between 3 and 12 approximately, and even more preferably between 5 and 1. 1. It can be adjusted to the desired value by means of acidifying or alkalizing agents usually used in dyeing keratinous fibers and as defined above.
- the ready-to-use composition with or without an oxidizing agent which is finally applied to the keratinous fibers may be in various forms, such as in the form of liquids, creams, gels or in any other form suitable for dyeing keratinous fibers, and in particular human hair.
- the invention also relates to a multi-compartment device or "kit" of dyeing in which a first compartment contains the dye composition of the present invention defined above without any oxidizing agent and a second compartment contains a composition comprising one or more several oxidizing agents.
- a second device is constituted by a first compartment containing a composition comprising one or more oxidation bases selected from the compound of formula (I) or its addition salts with an acid, optionally one or more additional oxidation bases different from the compound of formula (I) or its salts and optionally one or more couplers and a second compartment containing a composition comprising the or the above-mentioned pearlescent agents.
- a third device may optionally comprise the two compartments of the second device plus a third compartment containing a composition comprising one or more oxidizing agents.
- These devices may be equipped with means for delivering the desired product onto the hair, such as the devices described in patent FR-2 586 913. From these devices, it is possible to dye the keratin fibers from a process which comprises mixing the compositions contained in each of the compartments of said devices and applying the resulting mixture to the keratinous fibers for a time sufficient to develop the desired coloration.
- composition was diluted extemporaneously with 1.5 times its weight in hydrogen peroxide at 20 volumes.
- the mixture was applied to 90% white natural gray hair at the rate of 10 g per 1 g of hair for 30 minutes at room temperature.
- the hair was then rinsed, washed with standard shampoo and dried.
- the hair color was evaluated visually.
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Abstract
The invention relates to a composition for coloring keratin fibers, including, in a suitable dyeing medium: one or more oxidation bases selected from the compound of formula (I) and the acid addition salts thereof; and one or more pearling agents. The invention also relates to a dyeing method implementing said composition, comprising applying the abovementioned dyeing composition to the fibers with or without an oxidizing agent. The invention further relates to devices comprising a plurality of compartments.
Description
COMPOSITION TINCTORIALE COMPRENANT UNE BASE D'OXYDATION PARA- PHENYLENE DIAMINE SECONDAIRE ET UN AGENT NACRANT TINCTORIAL COMPOSITION COMPRISING A PARA-PHENYLENE DIAMINE SECONDARY OXIDATION BASE AND A NACRANT AGENT
L'invention a pour objet une composition tinctoriale comprenant au moins une base d'oxydation para-phénylènediamine secondaire particulière et au moins un agent nacrant. L'invention a aussi pour objet un procédé de teinture de fibres kératiniques, en particulier humaines telles que les cheveux, mettant en œuvre cette composition, ainsi que des dispositifs à plusieurs compartiments appropriés. II est connu de teindre les fibres kératiniques et en particulier les cheveux humains avec des compositions tinctoriales contenant des précurseurs de colorant d'oxydation, appelés généralement bases d'oxydation, tels que des ortho ou paraphénylènediamines, des ortho ou paraaminophénols et des composés hétérocycliques. Ces bases d'oxydation sont des composés incolores ou faiblement colorés qui, associés à des produits oxydants, peuvent donner naissance par un processus de condensation oxydative à des composés colorés.The invention relates to a dye composition comprising at least one particular para-phenylenediamine oxidation base and at least one pearlescent agent. The invention also relates to a process for dyeing keratinous fibers, in particular human fibers such as the hair, using this composition, as well as devices with several appropriate compartments. It is known to dye keratin fibers and in particular human hair with dye compositions containing oxidation dye precursors, generally known as oxidation bases, such as ortho or para-phenylenediamines, ortho or para-aminophenols and heterocyclic compounds. These oxidation bases are colorless or weakly colored compounds which, when combined with oxidizing products, can give rise to colored compounds by a process of oxidative condensation.
On sait également que l'on peut faire varier les nuances obtenues avec ces bases d'oxydation en les associant à des coupleurs ou modificateurs de coloration, ces derniers étant choisis notamment parmi les métadiamines aromatiques, les métaaminophénols, les métadiphénols et certains composés hétérocycliques tels que des composés indoliques. La variété des molécules mises en jeu au niveau des bases d'oxydation et des coupleurs, permet l'obtention d'une riche palette de couleurs.It is also known that the shades obtained with these oxidation bases can be varied by combining them with couplers or color modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as than indolic compounds. The variety of molecules involved in oxidation bases and couplers, allows to obtain a rich palette of colors.
La coloration dite "permanente" obtenue grâce à ces colorants d'oxydation, doit par ailleurs satisfaire un certain nombre d'exigences. Ainsi, elle doit être sans inconvénient sur le plan toxicologique, elle doit permettre d'obtenir des nuances dans l'intensité souhaitée et présenter une bonne tenue face aux agents extérieurs tels que la lumière, les intempéries, le lavage, les ondulations permanentes, la transpiration et les frottements.The so-called "permanent" coloration obtained with these oxidation dyes must also meet a certain number of requirements. Thus, it must be harmless from the toxicological point of view, it must make it possible to obtain shades in the desired intensity and to have good resistance to external agents such as light, bad weather, washing, permanent undulations, sweating and friction.
Les colorants doivent également permettre de couvrir les cheveux blancs, et être enfin les moins sélectifs possibles, c'est-à-dire permettre d'obtenir des écarts de coloration les plus faibles possibles tout au long d'une même fibre kératinique, qui est en général différemment sensibilisée (i.e. abîmée) entre sa pointe et sa racine.The dyes must also make it possible to cover the white hair, and finally be the least selective possible, that is to say, to obtain the lowest possible color differences throughout the same keratin fiber, which is in general differently sensitized (ie damaged) between its point and its root.
Il est déjà connu d'utiliser des bases d'oxydation du type para-phénylène diamine secondaire de formule (I) ci-dessous pour la coloration des fibres kératiniques, notamment les cheveux. En particulier, une telle base est divulguée dans les documents EP1580184 et EP0055386. Cette base présente comme inconvénients de conduire à des colorations insuffisamment intenses ou chromatiques et/ou trop sélectives.
Le but de la présente invention est d'obtenir une composition pour la coloration des cheveux qui présente des propriétés tinctoriales améliorées en termes d'intensité ou de chromaticité, et/ou de sélectivité et/ou de résistance aux agents extérieurs.It is already known to use oxidation bases of the para-phenylene diamine secondary type of formula (I) below for dyeing keratinous fibers, especially the hair. In particular, such a base is disclosed in EP1580184 and EP0055386. This base has the drawbacks of leading to insufficiently intense or chromatic and / or too selective staining. The object of the present invention is to obtain a composition for hair dyeing which has improved dyeing properties in terms of intensity or chromaticity, and / or selectivity and / or resistance to external agents.
Ce but est atteint avec la présente invention qui a pour objet une composition de coloration des fibres kératiniques comprenant, dans un milieu de teinture approprié,This object is achieved with the present invention which relates to a coloring composition of keratinous fibers comprising, in an appropriate dyeing medium,
- une ou plusieurs bases d'oxydation choisies parmi le composé de formule (I) ou ses sels d'addition avec un acide,one or more oxidation bases selected from the compound of formula (I) or its addition salts with an acid,
L'invention a aussi pour objet un procédé de teinture mettant en œuvre cette composition.The invention also relates to a dyeing process using this composition.
Elle a également pour objet un dispositif à plusieurs compartiments comprenant dans l'un d'entre eux, la composition tinctoriale selon l'invention sans oxydant, et dans un autre, une composition comprenant un ou plusieurs agents oxydants.It also relates to a multi-compartment device comprising in one of them, the dye composition according to the invention without oxidant, and in another, a composition comprising one or more oxidizing agents.
Selon une autre variante de l'invention, le dispositif comprend un premier compartiment renfermant une ou plusieurs bases d'oxydation choisies parmi le composé de formule (I) ou ses sels avec un acide et éventuellement une ou plusieurs bases d'oxydation différentes du composé de formule (I) ou de ses sels et éventuellement un ou plusieurs coupleurs ; un deuxième compartiment renfermant une composition comprenant un ou plusieurs agents nacrants et éventuellement un troisième compartiment renfermant une composition comprenant un ou plusieurs agents oxydantsAccording to another variant of the invention, the device comprises a first compartment containing one or more oxidation bases chosen from the compound of formula (I) or its salts with an acid and optionally one or more different oxidation bases of the compound of formula (I) or its salts and optionally one or more couplers; a second compartment containing a composition comprising one or more pearlescent agents and optionally a third compartment containing a composition comprising one or more oxidizing agents
La composition de la présente invention permet en particulier d'obtenir une composition de coloration de fibres kératiniques qui convienne pour une utilisation en coloration d'oxydation et permettent d'obtenir une coloration aux nuances variées, intenses ou chromatiques, esthétiques, peu sélectives et résistant bien aux diverses agressions que peuvent subir les cheveux tels que les shampooings, la sueur et les déformations permanentes et la lumière.The composition of the present invention makes it possible in particular to obtain a keratinous fiber coloring composition which is suitable for use in oxidation dyeing and makes it possible to obtain a coloring with varied shades, intense or chromatic, aesthetic, not very selective and resistant. well to the various aggressions that can undergo the hair such as the shampoos, the sweat and the permanent deformations and the light.
Il est à noter que dans ce qui va suivre, et à moins d'une autre indication, les bornes d'un domaine de valeurs sont comprises dans ce domaine.It should be noted that in what follows, and unless otherwise indicated, the boundaries of a domain of values are included in this area.
Le composé de formule (I) peut être sous forme de sels d'addition notamment choisis parmi les sels d'addition avec un acide tels que les chlorhydrates, les bromhydrates, les sulfates, les citrates, les succinates, les tartrates, les lactates, les tosylates, les benzènesulfonates, les phosphates et les acétates.
Le composé de formule (I) ou ses sels sont en général présents chacun en quantité comprise entre 0,001 à 10 % en poids par rapport au poids total de la composition tinctoriale, de préférence entre 0,005 et 6 % en poids.The compound of formula (I) may be in the form of addition salts chosen especially from acid addition salts such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates. The compound of formula (I) or its salts are generally present each in an amount of between 0.001 to 10% by weight relative to the total weight of the dye composition, preferably between 0.005 and 6% by weight.
La composition tinctoriale de l'invention peut éventuellement comprendre une ou plusieurs bases d'oxydation additionnelles conventionnellement utilisées pour la teinture de fibres kératiniques, différentes du composé de formule (I) ou de ses sels.The dye composition of the invention may optionally comprise one or more additional oxidation bases conventionally used for dyeing keratinous fibers, different from the compound of formula (I) or its salts.
A titre d'exemple, ces bases d'oxydation additionnelles sont choisies parmi les para- phénylènediamines différentes du composé de formule (I) et de ses sels d'addition, les bis- phénylalkylènediamines, les para-aminophénols, les bis-para-aminophénols, les ortho- aminophénols, les bases hétérocycliques.By way of example, these additional oxidation bases are chosen from the different para-phenylenediamines of the compound of formula (I) and of its addition salts, bisphenylalkylenediamines, para-aminophenols, bis-para-amines and aminophenols, ortho-aminophenols, heterocyclic bases.
Parmi les para-phénylènediamines, on peut citer à titre d'exemple, la para- phénylènediamine, la para-toluènediamine, la 2-chloro para-phénylènediamine, la 2,3- diméthyl para-phénylènediamine, la 2,6-diméthyl para-phénylènediamine, la 2,6-diéthyl para-phénylènediamine, la 2,5-diméthyl para-phénylènediamine, la N,N-diméthyl para- phénylènediamine, la N,N-diéthyl para-phénylènediamine, la N,N-dipropyl para- phénylènediamine, la 4-amino N,N-diéthyl 3-méthyl aniline, la N,N-bis-(β-hydroxyéthyl) para- phénylènediamine, la 4-N,N-bis-(β-hydroxyéthyl)amino 2-méthyl aniline, la 4-N,N-bis-(β-hydroxyéthyl)amino 2-chloro aniline, la 2-β-hydroxyéthyl para- phénylènediamine, la 2-fluoro para-phénylènediamine, la 2-isopropyl para- phénylènediamine, la N-(β-hydroxypropyl) para-phénylènediamine, la 2-hydroxyméthyl para- phénylènediamine, la N,N-diméthyl 3-méthyl para-phénylènediamine, la N,N-(éthyl, β- hydroxyéthyl) para-phénylènediamine, la N-(β,γ-dihydroxypropyl) para-phénylènediamine, la N-(4'-aminophényl) para-phénylènediamine, la N-phényl para-phénylènediamine, la 2-β-hydroxyéthyloxy para-phénylènediamine, la 2-β-acétylaminoéthyloxy para- phénylènediamine, la N-(β-méthoxyéthyl) para-phénylène-diamine, la 4- aminophénylpyrrolidine, la 2-thiényl para-phénylènediamine, le 2-β hydroxyéthylamino 5- amino toluène, la 3-hydroxy 1-(4'-aminophényl)pyrrolidine et leurs sels d'addition avec un acide.Among the para-phenylenediamines, there may be mentioned by way of example, para-phenylenediamine, para-toluenediamine, 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- (β-hydroxyethyl) para-phenylenediamine, 4-N, N-bis- (β-hydroxyethyl) amino 2- methyl aniline, 4-N, N-bis- (β-hydroxyethyl) amino-2-chloroaniline, 2-β-hydroxyethyl-para-phenylenediamine, 2-fluoro-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N- (β-hydroxypropyl) para-phenylenediamine, 2-hydroxymethyl-para-phenylenediamine, N, N-dimethyl-3-methyl-para-phenylenediamine, N, N- (ethyl, β-hydroxyethyl) para-phenylenediamine, N- (β, γ-dihydroxypropyl) para-phenylenediamine, N- (4'-aminophenyl) para-phenylenediamine, N-phenyl para-phenylenediamine, 2-β-hydroxyethyloxy para-phenylenediamine, 2-β-acetylaminoethyloxy para-phenylenediamine, N- (β-methoxyethyl) para-phenylenediamine, 4-aminophenylpyrrolidine, 2-thienyl para-phenylenediamine, 2-β-hydroxyethylamino-5-amino-toluene, 3-hydroxy-1- (4 ') aminophenyl) pyrrolidine and their addition salts with an acid.
Parmi les para-phénylènediamines citées ci-dessus, la para-phénylènediamine, la para- toluènediamine, la 2-isopropyl para-phénylènediamine, la 2-β-hydroxyéthyl para- phénylènediamine, la 2-β-hydroxyéthyloxy para-phénylène-diamine, la 2,6-diméthyl para- phénylènediamine, la 2,6-diéthyl para-phénylènediamine, la 2,3-diméthyl para- phénylènediamine, la N,N-bis-(β-hydroxyéthyl) para-phénylènediamine, la 2-chloro para- phénylènediamine, la 2-β-acétylaminoéthyloxy para-phénylènediamine, et leurs sels d'addition avec un acide sont particulièrement préférées.Among the para-phenylenediamines mentioned above, para-phenylenediamine, para-toluenediamine, 2-isopropyl para-phenylenediamine, 2-β-hydroxyethyl para-phenylenediamine, 2-β-hydroxyethyloxy para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, N, N-bis- (β-hydroxyethyl) para-phenylenediamine, 2-chloro para-phenylenediamine, 2-β-acetylaminoethyloxy para-phenylenediamine, and their addition salts with an acid are particularly preferred.
Parmi les bis-phénylalkylènediamines, on peut citer à titre d'exemple, le N,N'-bis-(β- hydroxyéthyl) N,N'-bis-(4'-aminophényl) 1 ,3-diamino propanol, la N,N'-bis-(β-hydroxyéthyl) N,N'-bis-(4'-aminophényl) éthylènediamine, la N,N'-bis-(4-aminophényl)
tétraméthylènediamine, la N,N'-bis-(β-hydroxyéthyl) N,N'-bis-(4-aminophényl) tétraméthylènediamine, la N,N'-bis-(4-méthyl-aminophényl) tétraméthylènediamine, la N, N'- bis-(éthyl) N,N'-bis-(4'-amino, 3'-méthylphényl) éthylènediamine, le 1 ,8-bis-(2,5-diamino phénoxy)-3,6-dioxaoctane, et leurs sels d'addition avec un acide. Parmi les para-aminophénols, on peut citer à titre d'exemple, le para-aminophénol, le 4- amino 3-méthyl phénol, le 4-amino 3-fluoro phénol, le 4-amino 3-hydroxyméthyl phénol, le 4- amino 2-méthyl phénol, le 4-amino 2-hydroxyméthyl phénol, le 4-amino 2-méthoxyméthyl phénol, le 4-amino 2-aminométhyl phénol, le 4-amino 2-(β-hydroxyéthyl aminométhyl) phénol, le 4-amino 2-fluoro phénol, le 1-hydroxy-4-methylamino-benzene, le 2-2'- methylenebis-4-amino phénol et leurs sels d'addition avec un acide.Among the bis-phenylalkylenediamines, N, N'-bis- (β-hydroxyethyl) N, N'-bis (4'-aminophenyl) -1,3-diamino propanol, N, may be mentioned by way of example. N, N'-bis- (β-hydroxyethyl) N, N'-bis- (4'-aminophenyl) ethylenediamine, N, N'-bis- (4-aminophenyl) tetramethylenediamine, N, N'-bis- (β-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-diamino phenoxy) -3,6-dioxaoctane, and their addition salts with an acid. Examples of para-aminophenols include para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluoro phenol, 4-amino-3-hydroxymethylphenol, 4- amino 2-methyl phenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- (β-hydroxyethylaminomethyl) phenol, 4- amino 2-fluoro phenol, 1-hydroxy-4-methylamino-benzene, 2-2'-methylenebis-4-amino phenol and their addition salts with an acid.
Parmi les ortho-aminophénols, on peut citer à titre d'exemple, le 2-amino phénol, le 2- amino 5-méthyl phénol, le 2-amino 6-méthyl phénol, le 5-acétamido 2-amino phénol, et leurs sels d'addition avec un acide.Among the ortho-aminophenols, there may be mentioned by way of example, 2-amino phenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol, 5-acetamido-2-amino phenol, and their addition salts with an acid.
Parmi les bases hétérocycliques, on peut citer à titre d'exemple, les dérivés pyridiniques, les dérivés pyrimidiniques et les dérivés pyrazoliques.Among the heterocyclic bases that may be mentioned by way of example are pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
Parmi les dérivés pyridiniques, on peut citer les composés décrits par exemple dans les brevets GB 1 026 978 et GB 1 153 196, comme la 2,5-diamino pyridine, la 2-(4- méthoxyphényl)amino 3-amino pyridine, la 2,3-diamino 6-méthoxy pyridine, la 2-(β- méthoxyéthyl)amino 3-amino 6-méthoxy pyridine, la 3,4-diamino pyridine, et leurs sels d'addition avec un acide.Among the pyridine derivatives, mention may be made of the compounds described for example in patents GB 1 026 978 and GB 1 153 196, such as 2,5-diaminopyridine, 2- (4-methoxyphenyl) amino 3-amino pyridine, 2,3-diamino-6-methoxy pyridine, 2- (β-methoxyethyl) amino-3-amino-6-methoxy pyridine, 3,4-diamino pyridine, and their addition salts with an acid.
Parmi les dérivés pyrimidiniques, on peut citer les composés décrits par exemple dans les brevets DE 2359399 ; JP 88-169571 ; JP 05-63124 ; EP 0770375 ou demande de brevet WO 96/15765 comme la 2,4,5, 6-tétra-aminopyrimidine, la 4-hydroxy 2,5,6- triaminopyrimidine, la 2-hydroxy 4,5,6-triaminopyrimidine, la 2,4-dihydroxy 5,6- diaminopyrimidine, la 2,5,6-triaminopyrimidine, et les dérivés pyrazolo-pyrimidiniques tels ceux mentionnés dans la demande de brevet FR-A-2750048 et parmi lesquels on peut citer la pyrazolo-[1 ,5-a]-pyrimidine-3,7-diamine ; la 2,5-diméthyl pyrazolo-[1 ,5-a]-pyrimidine-3,7- diamine ; la pyrazolo-[1 ,5-a]-pyrimidine-3,5-diamine ; la 2,7-diméthyl pyrazolo-[1 ,5-a]- pyrimidine-3,5-diamine ; le 3-amino pyrazolo-[1 ,5-a]-pyrimidin-7-ol ; le 3-amino pyrazolo-[1 ,5- a]-pyrimidin-5-ol ; le 2-(3-amino pyrazolo-[1 ,5-a]-pyrimidin-7-ylamino)-éthanol, le 2-(7-amino pyrazolo-[1 ,5-a]-pyrimidin-3-ylamino)-éthanol, le 2-[(3-amino-pyrazolo[1 ,5-a]pyrimidin-7-yl)- (2-hydroxy-éthyl)-amino]-éthanol, le 2-[(7-amino-pyrazolo[1 ,5-a]pyrimidin-3-yl)-(2-hydroxy- éthyl)-amino]-éthanol, la 5,6-diméthyl pyrazolo-[1 ,5-a]-pyrimidine-3,7-diamine, la 2,6-diméthyl pyrazolo-[1 ,5-a]-pyrimidine-3,7-diamine, la 2, 5, N 7, N 7-tetraméthyl pyrazolo- [1 ,5-a]-pyrimidine-3,7-diamine, la 3-amino-5-méthyl-7-imidazolylpropylamino pyrazolo-[1 ,5- a]-pyrimidine et leurs sels d'addition avec un acide et leurs formes tautomères, lorsqu'il existe un équilibre tautomérique.
Parmi les dérivés pyrazoliques, on peut citer les composés décrits dans les brevets DE 3843892, DE 4133957 et demandes de brevet WO 94/08969, WO 94/08970, FR-A-2 733 749 et DE 195 43 988 comme le 4,5-diamino 1-méthyl pyrazole, le 4,5-diamino 1-(β- hydroxyéthyl) pyrazole, le 3,4-diamino pyrazole, le 4,5-diamino 1-(4'-chlorobenzyl) pyrazole, le 4,5-diamino 1 ,3-diméthyl pyrazole, le 4,5-diamino 3-méthyl 1-phényl pyrazole, le 4,5- diamino 1-méthyl 3-phényl pyrazole, le 4-amino 1 ,3-diméthyl 5-hydrazino pyrazole, le 1-benzyl 4,5-diamino 3-méthyl pyrazole, le 4,5-diamino 3-tert-butyl 1-méthyl pyrazole, le 4,5- diamino 1-tert-butyl 3-méthyl pyrazole, le 4,5-diamino i-(β-hydroxyéthyl) 3-méthyl pyrazole, le 4,5-diamino 1-éthyl 3-méthyl pyrazole, le 4,5-diamino 1-éthyl 3-(4'-méthoxyphényl) pyrazole, le 4,5-diamino 1-éthyl 3-hydroxyméthyl pyrazole, le 4,5-diamino 3-hydroxyméthyl 1-méthyl pyrazole, le 4,5-diamino 3-hydroxyméthyl 1-isopropyl pyrazole, le 4,5-diamino 3- méthyl 1-isopropyl pyrazole, le 4-amino 5-(2'-aminoéthyl)amino 1 ,3-diméthyl pyrazole, le 3,4,5-triamino pyrazole, le 1-méthyl 3,4,5-triamino pyrazole, le 3,5-diamino 1-méthyl 4- méthylamino pyrazole, le 3,5-diamino 4-(β-hydroxyéthyl)amino 1-méthyl pyrazole, et leurs sels d'addition avec un acide.Among the pyrimidine derivatives, mention may be made of the compounds described, for example, in 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, , 4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine, and pyrazolopyrimidine derivatives such as those mentioned in patent application FR-A-2750048 and among which mention may be made of pyrazolo [1, 5-a] -pyrimidine-3,7-diamine; 2,5-dimethyl pyrazolo [1,5-a] pyrimidine-3,7-diamine; pyrazolo [1,5-a] pyrimidine-3,5-diamine; 2,7-dimethyl pyrazolo [1,5-a] pyrimidine-3,5-diamine; 3-amino pyrazolo [1,5-a] pyrimidin-7-ol; 3-amino pyrazolo [1,5-a] pyrimidin-5-ol; 2- (3-amino pyrazolo [1,5-a] pyrimidin-7-ylamino) ethanol, 2- (7-amino pyrazolo [1,5-a] pyrimidin-3-ylamino) - ethanol, 2 - [(3-amino-pyrazolo [1,5-a] pyrimidin-7-yl) - (2-hydroxyethyl) amino] ethanol, 2 - [(7-amino-pyrazolo [ 1,5-a] pyrimidin-3-yl) - (2-hydroxyethyl) amino] ethanol, 5,6-dimethyl pyrazolo [1,5-a] pyrimidine-3,7-diamine, 2,6-dimethyl pyrazolo [1,5-a] pyrimidine-3,7-diamine, 2,5-N, 7-N-7-tetramethyl-pyrazolo [1,5-a] -pyrimidine-3, 7-diamine, 3-amino-5-methyl-7-imidazolylpropylamino pyrazolo [1,5-a] pyrimidine and their acid addition salts and their tautomeric forms, when tautomeric equilibrium exists. Among the pyrazole derivatives, mention may be made of the compounds described in DE 3843892, DE 4133957 and patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988 as the 4.5 1-methyl pyrazole, 4,5-diamino-1- (β-hydroxyethyl) pyrazole, 3,4-diamino pyrazole, 4,5-diamino-1- (4'-chlorobenzyl) pyrazole, 4,5 1-diamino-1,3-dimethyl pyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydrazino pyrazole 1-Benzyl-4,5-diamino-3-methyl-pyrazole, 4,5-diamino-3-tert-butyl-1-methyl-pyrazole, 4,5-diamino-1-tert-butyl-3-methyl-pyrazole, 4, 5-diamino 1- (β-hydroxyethyl) 3-methyl pyrazole, 4,5-diamino-1-ethyl-3-methylpyrazole, 4,5-diamino-1-ethyl-3- (4'-methoxyphenyl) pyrazole, 4 5-diamino-1-ethyl-3-hydroxymethyl pyrazole, 4,5-diamino-3-hydroxymethyl-1-methyl pyrazole, 4,5-diamino-3-hydroxymethyl-1-isopropyl pyrazole, 4,5-diamino-3- methyl 1-isopropyl pyrazole, 4-amino-5- (2'-aminoethyl) amino-1,3-dimethyl pyrazole, 3,4,5-triamino pyrazole, 1-methyl-3,4,5-triamino pyrazole, 3,5-diamino-1-methyl-4-methylamino pyrazole, 3,5-diamino 4- (β-hydroxyethyl) amino-1-methyl pyrazole, and their addition salts with an acid.
On peut aussi citer les diaminopyrazolinones décrites dans la demande de brevet FR2886137 et en particulier la 2,3-diamino-6,7-dihydro-1 H,5H-pyrazol-1-one et ses sels.There may also be mentioned diaminopyrazolinones described in patent application FR2886137 and in particular 2,3-diamino-6,7-dihydro-1H, 5H-pyrazol-1-one and its salts.
D'une manière générale, les sels d'addition des bases d'oxydation et des coupleurs utilisables dans le cadre de l'invention sont notamment choisis parmi les sels d'addition avec un acide tels que les chlorhydrates, les bromhydrates, les sulfates, les citrates, les succinates, les tartrates, les lactates, les tosylates, les benzènesulfonates, les phosphates et les acétates et les sels d'addition avec une base telles que la soude, la potasse, l'ammoniaque, les aminés ou les alcanolamines.In general, the addition salts of the oxidation bases and couplers that can be used in the context of the invention are chosen especially from the addition salts with an acid such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates and addition salts with a base such as sodium hydroxide, potassium hydroxide, ammonia, amines or alkanolamines.
Lorsque la composition comprend une ou plusieurs bases d'oxydation additionnelles, celle(s)-ci représente(nt) plus particulièrement de 0,0005 à 12 % en poids par rapport au poids total de la composition tinctoriales, de préférence de 0,005 à 8 % en poids.When the composition comprises one or more additional oxidation bases, that (s) represents (s) more particularly from 0.0005 to 12% by weight relative to the total weight of the dyeing composition, preferably from 0.005 to 8 % in weight.
La composition tinctoriale selon l'invention peut également, éventuellement, comprendre un ou plusieurs coupleurs conventionnellement utilisés pour la teinture des fibres kératiniques. Parmi ces coupleurs, on peut notamment citer les méta-phénylènediamines, les méta-aminophénols, les méta-diphénols, les coupleurs naphtaléniques, les coupleurs hétérocycliques et leurs sels d'addition.The dye composition according to the invention may also optionally comprise one or more couplers conventionally used for dyeing keratinous fibers. Among these couplers, there may be mentioned meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalenic couplers, heterocyclic couplers and their addition salts.
A titre d'exemple de coupleur, on peut citer le 2-méthyl 5-aminophénol, le 5-N-(β- hydroxyéthyl)amino 2-méthyl phénol, le 6-chloro-2-méthyl-5-aminophénol, le 3-amino phénol, le 2,4-dichloro-3-aminophenol, le 5-amino-4-chloro-o-cresol, le 1 ,3-dihydroxy benzène, le 1 ,3-dihydroxy 2-méthyl benzène, le 4-chloro 1 ,3-dihydroxy benzène, le 2,4- diamino i-(β-hydroxyéthyloxy) benzène, le 2-amino 4-(β-hydroxyéthylamino) 1- méthoxybenzène, le 1 ,3-diamino benzène, le 1 ,3-bis-(2,4-diaminophénoxy) propane, la 3- uréido aniline, le 3-uréido 1-diméthylamino benzène, le sésamol, le 1-β-hydroxyéthylamino-
3,4-méthylènedioxybenzène, l'α-naphtol, le 2 méthyl-1-naphtol, le 1 ,5-dihydroxy naphtalene, le 2,7-naphthalenediol, le 1-acetoxy-2-methylnaphthalene, le 6-hydroxy indole, le 4-hydroxy indole, le 4-hydroxy N-méthyl indole, la 2-amino-3-hydroxy pyridine, la 6- hydroxy benzomorpholine la 3,5-diamino-2,6-diméthoxypyridine, les 2,6-dihydroxy-3-4- dimethyl pyridine, le 3-amino-2-methylamino-6-methoxypyridine, le 1-N-(β- hydroxyéthyl)amino-3,4-méthylène dioxybenzène, le 2,6-bis-(β-hydroxyéthylamino)toluène, le 3-methyl-1-phenyl-5-pyrazolone et leurs sels d'addition avec un acide.By way of example of a coupler, there may be mentioned 2-methyl-5-aminophenol, 5-N- (β-hydroxyethyl) amino-2-methylphenol, 6-chloro-2-methyl-5-aminophenol, 3 amino phenol, 2,4-dichloro-3-aminophenol, 5-amino-4-chloro-o-cresol, 1,3-dihydroxy benzene, 1,3-dihydroxy-2-methyl benzene, 4- chloro 1,3-dihydroxy benzene, 2,4-diamino 1- (β-hydroxyethyloxy) benzene, 2-amino 4- (β-hydroxyethylamino) -1-methoxybenzene, 1,3-diamino benzene, 1,3 bis-(2,4-diaminophenoxy) propane, 3-ureido aniline, 3-ureido 1-dimethylamino benzene, sesamol, 1-β-hydroxyethylamino- 3,4-methylenedioxybenzene, α-naphthol, 2-methyl-1-naphthol, 1,5-dihydroxy naphthalene, 2,7-naphthalenediol, 1-acetoxy-2-methylnaphthalene, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy N-methylindole, 2-amino-3-hydroxypyridine, 6-hydroxybenzomorpholine, 3,5-diamino-2,6-dimethoxypyridine, 2,6-dihydroxy-4-hydroxyindolines 3-4-dimethyl pyridine, 3-amino-2-methylamino-6-methoxypyridine, 1-N- (β-hydroxyethyl) amino-3,4-methylene dioxybenzene, 2,6-bis- (β-hydroxyethylamino) toluene, 3-methyl-1-phenyl-5-pyrazolone and their addition salts with an acid.
Dans la composition de la présente invention, le ou les coupleurs, s'ils sont présents, représentent en général une quantité comprise entre 0,001 et 10 % en poids par rapport au poids total de la composition tinctoriale, de préférence entre 0,005 et 6 % en poids.In the composition of the present invention, the coupler (s), if present, generally represent an amount of between 0.001% and 10% by weight relative to the total weight of the dyeing composition, preferably between 0.005% and 6% by weight. weight.
La composition tinctoriale conforme à l'invention peut en outre contenir un ou plusieurs colorants directs pouvant notamment être choisis parmi les colorants nitrés de la série benzénique, les colorants directs azoïques, les colorants directs méthiniques. Ces colorants directs peuvent être de nature non ionique, anionique ou cationique. Dans la composition de la présente invention, le ou les colorants directs, s'ils sont présents, représentent en général une quantité comprise entre 0,001 et 20 % en poids par rapport au poids total de la composition tinctoriale, de préférence entre 0,01 et 10 % en poids.The dye composition in accordance with the invention may also contain one or more direct dyes that may be chosen in particular from nitro dyes of the benzene series, azo direct dyes and methine direct dyes. These direct dyes may be nonionic, anionic or cationic in nature. In the composition of the present invention, the direct dye (s), if present, generally represent an amount of between 0.001% and 20% by weight relative to the total weight of the dyeing composition, preferably between 0.01% and 10% by weight.
Comme indiqué précédemment, la composition tinctoriale selon l'invention comprend un ou plusieurs agents nacrants.As indicated above, the dye composition according to the invention comprises one or more pearlescent agents.
Par agent nacrant, on entend au sens de la présente invention tout composé capable de conférer à la composition de l'invention un aspect ou effet irisé, iridescent, moiré ou métallisé.By pearlescent agent is meant in the sense of the present invention any compound capable of imparting to the composition of the invention an iridescent, iridescent, moiré or metallized appearance or effect.
De préférence, les agents nacrants utilisés dans la composition selon l'invention sont choisis parmi les composés suivants, seuls ou en mélanges : a) les esters de polyols ayant au moins deux atomes de carbone et d'acides gras à chaîne longue, plus particulièrement en Ci0-C3O et de préférence en C16-C22 ; tels que des mono ou diesters de polyols et d'acides gras ; de préférence les polyols sont l'éthylène glycol et les polyalkylène glycol ayant de 2 à 10 motifs d'oxyde d'éthylène ; b) les esters de monoalcools à chaîne longue (Ci0-C30) comme le cétyl palmitate ; c) les éthers d'alcools gras à chaîne longue, solides à une température inférieure ou égale à environ 300C tels que par exemple les dialkyléthers de formule (II) :Preferably, the pearling agents used in the composition according to the invention are chosen from the following compounds, alone or in mixtures: a) polyol esters having at least two carbon atoms and long chain fatty acids, more particularly Ci 0 -C 3 O and preferably C16-C22; such as mono or diesters of polyols and fatty acids; preferably the polyols are ethylene glycol and the polyalkylene glycol having from 2 to 10 ethylene oxide units; b) esters of long chain monohydric alcohols (Ci 0 -C 30 ) such as cetyl palmitate; c) ethers of long-chain fatty alcohols, solid at a temperature of less than or equal to about 30 ° C., such as, for example, the dialkyl ethers of formula (II):
R-O-R' (II) dans laquelle R et R', identiques ou différents, désignent un radical alkyle, saturé ou insaturé, linéaire ou ramifié, comportant de 10 à 30 atomes de carbone et de préférence de 14 à 24 atomes de carbone, R et R' étant choisis de façon telle que le composé de formule (II) soit solide à une température inférieure ou égale à 300C environ.
Plus particulièrement, R et R' désignent un radical stéaryle. Ces composés peuvent notamment être préparés selon le procédé décrit dans la demande de brevet DE 41 27 230. Un distéaryléther utilisable dans le cadre de la présente invention, est commercialisé sous la dénomination CUTINA STE par la société HENKEL ; d) les esters à chaîne longue (C10-C30) d'alcanolamides à chaîne longue (C10-C30) tels que le distéarate stéaramide diéthanolamide ou le stéarate stéaramide monoéthanolamide ; e) les alcools gras monochaînes ayant au moins 20 atomes de carbone tels que l'alcool béhénique ; et f) les composés ayant de 27 à 48 atomes de carbone et comportant un ou deux groupements éther et/ou thioéther ou sulfoxyde, et plus particulièrement, répondant à la formule (III) :ROR '(II) in which R and R', which may be identical or different, denote a linear or branched, saturated or unsaturated alkyl radical containing from 10 to 30 carbon atoms and preferably from 14 to 24 carbon atoms, R and R 'being chosen such that the compound of formula (II) is solid at a temperature of less than or equal to approximately 30 ° C. More particularly, R and R 'denote a stearyl radical. These compounds can in particular be prepared according to the process described in the patent application DE 41 27 230. A distearyl ether which can be used in the context of the present invention is marketed under the name CUTINA STE by the company HENKEL; d) the long chain (C 10 -C 30) esters of long chain alkanolamides (C 10 -C 30) such as distearate stearamide diethanolamide or stearate stearamide monoethanolamide; e) single-chain fatty alcohols having at least 20 carbon atoms such as behenic alcohol; and f) compounds having from 27 to 48 carbon atoms and having one or two ether and / or thioether or sulfoxide groups, and more particularly, corresponding to formula (III):
Ra-X[C2H3(OH)]-CH2-Y-Rb (III) dans laquelle R3 et Rb désignent indépendamment l'un de l'autre, des groupements linéaires en C12 à C24 ; X désigne un atome d'oxygène, un atome de soufre, un groupement sulfoxyde ou méthylène ;R a -X [C 2 H 3 (OH)] - CH 2 -YR b (III) wherein R 3 and R b denote independently of each other linear C 12 -C 24 groups ; X denotes an oxygen atom, a sulfur atom, a sulphoxide or methylene group;
Y désigne un atome d'oxygène, un atome de soufre, un groupement sulfoxyde ou méthylène ;Y denotes an oxygen atom, a sulfur atom, a sulphoxide or methylene group;
R3 et Rb a une valeur variant de 24 à 44 et de préférence de 28 à 40 inclus ; lorsque X ou Y désigne un groupement sulfoxyde, X ou Y ne désigne pas un atome de soufre.R 3 and R b has a value ranging from 24 to 44 and preferably from 28 to 40 inclusive; when X or Y denotes a sulphoxide group, X or Y denotes a sulfur atom.
Les composés de formule (III) utilisés de préférence conformément à l'invention, sont ceux pour lesquels X désigne un atome d'oxygène, Y désigne un groupement méthylène, et R3 et Rb désignent des radicaux ayant 12 à 22 atomes de carbone, ces composés pouvant être préparés selon le brevet EP457688 ; g) les oxydes de titane enrobés ou non, les micas et les mélanges de mica et d'oxyde de métaux (titane, fer) et/ou colorants comme par exemple les produits Colorona Russet, Cloisonne Orange, Cloisonne Rouge Flambe, Cloisonne Copper, Cloisonne GoId, Colorona Red GoId, Colorona Bright GoId, Timiron MP 25 GoId plus Cosmetic, Timica GoId Sparkle, (mélanges mica - oxyde de titane - oxyde de fer brun) ; les produits Timiron Super Silver, Prestige Pearlescent Pigments, Timiron Super Violet Cosmetic, Timiron MP-10 Pearl Flake, Timiron Super GoId, Flamenco Sparkle Blue, (mélanges mica - oxyde de titane) ; les produits Colorona Carminé Red, Duocrome RB, Cloisonne Red (mélanges mica - oxyde de titane - carmin ou carmin de cochenille); h) les cyclodextrines et en particulier la β-cyclodextrine.The compounds of formula (III) preferably used in accordance with the invention are those for which X denotes an oxygen atom, Y denotes a methylene group, and R 3 and R b denote radicals having 12 to 22 carbon atoms. these compounds may be prepared according to patent EP457688; g) coated or uncoated titanium oxides, micas and mixtures of mica and metal oxide (titanium, iron) and / or dyes, for example the products Colorona Russet, Cloisonne Orange, Cloisonne Rouge Flambe, Cloisonne Copper, Cloisonne GoId, Colorona Red GoId, Colorona Bright GoId, Timiron MP 25 GoId Plus Cosmetic, Timica GoId Sparkle, (mica-titanium oxide-brown iron oxide mixtures); Timiron Super Silver, Prestige Pearlescent Pigments, Timiron Super Violet Cosmetic, Timiron MP-10 Pearl Flake, Timiron Super GoId, Flamenco Sparkle Blue, (mica-titanium oxide blends); Colorona Carminé Red, Duocrome RB, Cloisonne Red (mica - titanium oxide - carmine or carmine cochineal mixtures); h) cyclodextrins and in particular β-cyclodextrin.
Les agents nacrants sont préférentiellement choisis parmi les mono- ou distéarate d'éthylène glycol ; le distéaryléther ; l'alcool béhénique ; l'oxyde de titane ; les micas ; les
mélanges de mica et d'oxyde de métaux (titane, fer) et/ou de colorants ainsi que le 1 - (hexadécyloxy)-2-octadécanol ; la β-cyclodextrine ou leurs mélanges.The pearlescent agents are preferably chosen from ethylene glycol mono- or distearate; distearyl ether; behenic alcohol; titanium oxide; micas; the mixtures of mica and metal oxide (titanium, iron) and / or dyes and 1 - (hexadecyloxy) -2-octadecanol; β-cyclodextrin or mixtures thereof.
La composition selon l'invention présente une teneur en agent(s) nacrant(s) variant de 0,05 à 10% en poids par rapport au poids de la composition tinctoriale, et de préférence de 0,1 à 5% en poids.The composition according to the invention has a nacreous agent (s) content ranging from 0.05 to 10% by weight relative to the weight of the dye composition, and preferably from 0.1 to 5% by weight.
Le milieu approprié pour la teinture appelé aussi support de teinture comprend généralement de l'eau ou un mélange d'eau et d'un ou plusieurs solvants comme par exemple les alcanols inférieurs en d-C4, tels que l'éthanol et l'isopropanol, les polyols comme le propylèneglycol, le dipropylèneglycol ou le glycérol, et les éthers de polyols comme le monométhyléther de dipropylèneglycol.The medium which is suitable for dyeing, also known as a dyeing medium, generally comprises water or a mixture of water and one or more solvents such as, for example, lower alkanols in dC 4 , such as ethanol and isopropanol, polyols such as propylene glycol, dipropylene glycol or glycerol, and polyol ethers such as dipropylene glycol monomethyl ether.
Le ou les solvants sont en général présents dans des proportions pouvant être comprises entre 1 et 40% en poids environ par rapport au poids total de la composition tinctoriale, et encore plus préférentiellement entre 3 et 30% en poids environ.The solvent or solvents are generally present in proportions which can be between 1 and 40% by weight approximately relative to the total weight of the dye composition, and even more preferably between 3 and 30% by weight approximately.
La composition tinctoriale conforme à l'invention peut également renfermer divers adjuvants utilisés classiquement dans les compositions pour la teinture des cheveux, tels que des agents tensioactifs anioniques, cationiques, non ioniques, amphotères, zwitterioniques, ou leurs mélanges, des polymères anioniques, cationiques, non ioniques, amphotères, zwitterioniques ou leurs mélanges, des agents épaississants minéraux ou organiques, et en particulier les épaississants associatifs polymères anioniques, cationiques, non ioniques et amphotères, des agents antioxydants, des agents de pénétration, des agents séquestrants, des parfums, des tampons, des agents dispersants, des agents de conditionnement tels que par exemple des silicones volatiles ou non volatiles, modifiées ou non modifiées, des agents filmogènes, des céramides, des agents conservateurs,. Les adjuvants ci dessus sont en général présents en quantité comprise pour chacun d'eux entre 0,01 et 20% en poids par rapport au poids de la composition.The dyeing composition in accordance with the invention may also contain various adjuvants conventionally used in compositions for dyeing hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants, or mixtures thereof, anionic, cationic polymers, nonionic, amphoteric, zwitterionic or mixtures thereof, inorganic or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrating agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as, for example, volatile or non-volatile silicones, modified or unmodified, film-forming agents, ceramides, preserving agents ,. The adjuvants above are generally present in an amount for each of them between 0.01 and 20% by weight relative to the weight of the composition.
Bien entendu, l'homme de l'art veillera à choisir ce ou ces éventuels composés complémentaires de manière telle que les propriétés avantageuses attachées intrinsèquement à la composition de teinture d'oxydation conforme à l'invention ne soient pas, ou substantiellement pas, altérées par la ou les adjonctions envisagées.Of course, one skilled in the art will take care to choose this or these optional additional compounds such that the advantageous properties intrinsically attached to the oxidation dyeing composition according to the invention are not, or not substantially impaired by the addition or additions envisaged.
Le pH de la composition tinctoriale conforme à l'invention est généralement compris entre 3 et 12 environ, et de préférence entre 5 et 1 1 environ. Il peut être ajusté à la valeur désirée au moyen d'agents acidifiants ou alcalinisants habituellement utilisés en teinture des fibres kératiniques ou bien encore à l'aide de systèmes tampons classiques. Parmi les agents acidifiants, on peut citer, à titre d'exemple, les acides minéraux ou organiques comme l'acide chlorhydrique, l'acide orthophosphorique, l'acide sulfurique, les acides carboxyliques comme l'acide acétique, l'acide tartrique, l'acide citrique, l'acide lactique, les acides sulfoniques.
Parmi les agents alcalinisants on peut citer, à titre d'exemple, l'ammoniaque, les carbonates alcalins, les silicates et métasilicates alcalins, les alcanolamines telles que les mono-, di- et triéthanolamines ainsi que leurs dérivés, les hydroxydes de sodium, potassium ou magnésium, les sels alcalins de pyrrolidine carboxylate et les composés de formule (IV) suivante :The pH of the dye composition according to the invention is generally between 3 and 12 approximately, and preferably between 5 and 1 1 approximately. It can be adjusted to the desired value by means of acidifying or alkalizing agents usually used for dyeing keratin fibers or else using conventional buffer systems. Among the acidifying agents, mention may be made, by way of example, of mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulphonic acids. Among the alkalinizing agents that may be mentioned, for example, ammonia, alkali carbonates, alkali silicates and metasilicates, alkanolamines such as mono-, di- and triethanolamines and their derivatives, sodium hydroxides, potassium or magnesium, the alkaline salts of pyrrolidine carboxylate and the compounds of formula (IV) below:
R»\ R \
N W N / \N W N / \
Rc Rd (IV) dans laquelle W est un reste propylène éventuellement substitué par un groupement hydroxyle ou un radical alkyle en d-C4 ; R3, Rb, Rc et Rd, identiques ou différents, représentent un atome d'hydrogène, un radical alkyle en CrC4 ou hydroxyalkyle en d-C4. La composition selon l'invention peut comprendre un ou plusieurs agents oxydants. Rc Rd (IV) in which W is a propylene residue optionally substituted by a hydroxyl group or an alkyl radical in dC 4 ; R 3 , Rb, Rc and R d , which may be identical or different, represent a hydrogen atom, a C 1 -C 4 alkyl or dC 4 hydroxyalkyl radical. The composition according to the invention may comprise one or more oxidizing agents.
Les agents oxydants sont ceux classiquement utilisés pour la teinture d'oxydation des fibres kératiniques sont par exemple le peroxyde d'hydrogène, le peroxyde d'urée, les bromates de métaux alcalins, les persels tels que les perborates et persulfates, les peracides et les enzymes oxydases parmi lesquelles on peut citer les peroxydases, les oxydo-réductases à 2 électrons telles que les uricases et les oxygénases à 4 électrons comme les laccases. Le peroxyde d'hydrogène est particulièrement préféré.The oxidizing agents are those conventionally used for the oxidation dyeing of keratin fibers, for example hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulfates, peracids and the like. oxidase enzymes, among which mention may be made of peroxidases, 2-electron oxidoreductases such as uricases and 4-electron oxygenases such as laccases. Hydrogen peroxide is particularly preferred.
La composition tinctoriale selon l'invention peut se présenter sous des formes diverses, telles que sous forme de liquides, de crèmes, de gels, ou sous toute autre forme appropriée pour réaliser une teinture des fibres kératiniques, et notamment des cheveux humains. Elle peut résulter du mélange au moment de l'emploi de plusieurs compositions.The dye composition according to the invention may be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratinous fibers, and especially human hair. It can result from mixing at the time of use of several compositions.
Dans une première variante elle résulte du mélange d'au moins deux compositions, l'une comprenant une ou plusieurs bases d'oxydation choisies parmi le composé de formule (I) ou ses sels d'addition avec un acide, éventuellement une ou plusieurs bases d'oxydation additionnelles différentes du composé de formule (I) ou de ses sels, et éventuellement un ou plusieurs coupleurs, une seconde composition comprenant le ou les agents nacrants et éventuellement une troisième composition comprenant un ou plusieurs agents oxydants tels que décrits précédemment.In a first variant, it results from the mixture of at least two compositions, one comprising one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid, optionally one or more bases. different additional oxidation of the compound of formula (I) or its salts, and optionally one or more couplers, a second composition comprising the pearlescent agent (s) and optionally a third composition comprising one or more oxidizing agents as described above.
Dans une seconde variante particulière, elle résulte du mélange de deux compositions, l'une comprenant une ou plusieurs bases d'oxydation choisies parmi le composé de formule (I) ou ses sels d'addition avec un acide, le ou les agents nacrants, éventuellement une ou plusieurs bases d'oxydation additionnelles différentes du composé de formule (I) ou de ses sels, et éventuellement un ou plusieurs coupleurs, une autre composition comprenant un ou plusieurs agents oxydants tels que décrits précédemment.In a second particular variant, it results from the mixture of two compositions, one comprising one or more oxidation bases selected from the compound of formula (I) or its addition salts with an acid, the pearlescent agent (s), optionally one or more different additional oxidation bases of the compound of formula (I) or of its salts, and optionally one or more couplers, another composition comprising one or more oxidizing agents as described above.
La composition de l'invention est donc appliquée sur les cheveux pour la coloration des fibres kératiniques soit telle quelle soit en présence d'un ou plusieurs agents oxydants, pour la coloration des fibres kératiniques.
Le procédé de la présente invention est un procédé dans lequel on applique sur les fibres la composition sans oxydant selon la présente invention telle que définie précédemment, soit seule soit en présence d'un ou plusieurs agents oxydants.The composition of the invention is therefore applied to the hair for dyeing keratinous fibers either as such or in the presence of one or more oxidizing agents, for dyeing keratinous fibers. The process of the present invention is a process in which the non-oxidizing composition according to the present invention as defined above, either alone or in the presence of one or more oxidizing agents, is applied to the fibers.
La couleur peut être révélée à pH acide, neutre ou alcalin De plus, le ou les agents oxydants, s'ils sont présents, peuvent être ajoutés à la composition de l'invention juste au moment de l'emploi ou bien encore être mis en œuvre à partir d'une composition oxydante le(s) contenant, appliquée simultanément ou séquentiellement à la composition de l'invention,The color may be revealed at acidic, neutral or alkaline pH In addition, the oxidizing agent (s), if present, may be added to the composition of the invention just at the time of use or may be using an oxidizing composition containing them, applied simultaneously or sequentially to the composition of the invention,
Selon un mode de réalisation particulier et préféré de l'invention, la composition selon la présente invention exempte d'agent(s) oxydant(s) est mélangée, de préférence au moment de l'emploi, à une composition comprenant, dans un milieu approprié pour la teinture, un ou plusieurs agents oxydants. Le mélange obtenu est ensuite appliqué sur les fibres kératiniques.According to a particular and preferred embodiment of the invention, the composition according to the present invention free of oxidizing agent (s) is mixed, preferably at the time of use, with a composition comprising, in a medium suitable for dyeing, one or more oxidizing agents. The mixture obtained is then applied to the keratinous fibers.
Les agents oxydants sont ceux indiqués précédemment. Que ce soit avec ou sans oxydant, le temps de pause de la ou des compositions varie de 3 à 50 minutes environ, de préférence 5 à 30 minutes environ.The oxidizing agents are those indicated above. Whether with or without an oxidant, the pause time of the composition (s) varies from approximately 3 to 50 minutes, preferably from 5 to approximately 30 minutes.
La température durant l'application est classiquement comprise entre la température ambiante (entre 15 à 25°C) et 800C, de préférence entre la température ambiante et 600C.The temperature during the application is conventionally between room temperature (between 15 and 25 ° C.) and 80 ° C., preferably between room temperature and 60 ° C.
A l'issue de ce temps de pause, les fibres kératiniques sont rincées à l'eau, éventuellement lavées au shampooing, rincées à l'eau à nouveau puis séchées.At the end of this pause time, the keratinous fibers are rinsed with water, optionally washed with shampoo, rinsed with water again and then dried.
La composition oxydante peut également renfermer divers adjuvants utilisés classiquement dans les compositions pour la teinture des cheveux et tels que définis précédemment.The oxidizing composition may also contain various adjuvants conventionally used in compositions for dyeing hair and as defined above.
Le pH de la composition oxydante renfermant l'agent oxydant est tel qu'après mélange avec la composition tinctoriale, le pH de la composition résultante appliquée sur les fibres kératiniques varie de préférence entre 3 et 12 environ, et encore plus préférentiellement entre 5 et 1 1. Il peut être ajusté à la valeur désirée au moyen d'agents acidifiants ou alcalinisants habituellement utilisés en teinture des fibres kératiniques et tels que définis précédemment. La composition prête à l'emploi avec ou sans agent oxydant qui est finalement appliquée sur les fibres kératiniques peut se présenter sous des formes diverses, telles que sous forme de liquides, de crèmes, de gels ou sous toute autre forme appropriée pour réaliser une teinture des fibres kératiniques, et notamment des cheveux humains.The pH of the oxidizing composition containing the oxidizing agent is such that, after mixing with the dyeing composition, the pH of the resulting composition applied to the keratinous fibers preferably varies between 3 and 12 approximately, and even more preferably between 5 and 1. 1. It can be adjusted to the desired value by means of acidifying or alkalizing agents usually used in dyeing keratinous fibers and as defined above. The ready-to-use composition with or without an oxidizing agent which is finally applied to the keratinous fibers may be in various forms, such as in the form of liquids, creams, gels or in any other form suitable for dyeing keratinous fibers, and in particular human hair.
L'invention a aussi pour objet un dispositif à plusieurs compartiments ou "kit" de teinture dans lequel un premier compartiment renferme la composition tinctoriale de la présente invention définie ci-dessus dépourvue d'agent oxydant et un deuxième compartiment renferme une composition comprenant un ou plusieurs agents oxydants.The invention also relates to a multi-compartment device or "kit" of dyeing in which a first compartment contains the dye composition of the present invention defined above without any oxidizing agent and a second compartment contains a composition comprising one or more several oxidizing agents.
Un second dispositif est constitué par un premier compartiment contenant une composition comprenant une ou plusieurs bases d'oxydation choisies parmi le composé de
formule (I) ou ses sels d'addition avec un acide, éventuellement une ou plusieurs bases d'oxydation additionnelles différentes du composé de formule (I) ou de ses sels et éventuellement un ou plusieurs coupleurs et un second compartiment renfermant une composition comprenant le ou les agents nacrants précités. Un troisième dispositif peut éventuellement comprendre les deux compartiments du second dispositif plus un troisième compartiment renfermant une composition comprenant un ou plusieurs agents oxydants.A second device is constituted by a first compartment containing a composition comprising one or more oxidation bases selected from the compound of formula (I) or its addition salts with an acid, optionally one or more additional oxidation bases different from the compound of formula (I) or its salts and optionally one or more couplers and a second compartment containing a composition comprising the or the above-mentioned pearlescent agents. A third device may optionally comprise the two compartments of the second device plus a third compartment containing a composition comprising one or more oxidizing agents.
Ces dispositifs peuvent être équipés d'un moyen permettant de délivrer sur les cheveux le produit souhaité, tel que les dispositifs décrits dans le brevet FR-2 586 913. A partir de ces dispositifs, il est possible de teindre les fibres kératiniques à partir d'un procédé qui comprend le mélange des compositions contenues dans chacun des compartiments desdits dispositifs et l'application du mélange obtenu sur les fibres kératiniques pendant un temps suffisant pour développer la coloration désirée.These devices may be equipped with means for delivering the desired product onto the hair, such as the devices described in patent FR-2 586 913. From these devices, it is possible to dye the keratin fibers from a process which comprises mixing the compositions contained in each of the compartments of said devices and applying the resulting mixture to the keratinous fibers for a time sufficient to develop the desired coloration.
L'exemple qui suit sert à illustrer l'invention sans toutefois présenter un caractère limitatif.
The following example serves to illustrate the invention without being limiting in nature.
ExempleExample
On prépare la composition suivante (les quantités exprimées en grammes sauf mention contraire :The following composition is prepared (the quantities expressed in grams unless otherwise stated:
Mode d'applicationMode of application
La composition a été diluée extemporanément avec 1 ,5 fois son poids en eau oxygénée à 20 volumes.The composition was diluted extemporaneously with 1.5 times its weight in hydrogen peroxide at 20 volumes.
Le mélange a été appliqué sur des cheveux gris naturels à 90% blancs à raison de 10 g pour 1 g de cheveux pendant 30 minutes, à température ambiante.The mixture was applied to 90% white natural gray hair at the rate of 10 g per 1 g of hair for 30 minutes at room temperature.
Les cheveux ont ensuite été rincés, lavés avec un shampooing standard et séchés.The hair was then rinsed, washed with standard shampoo and dried.
RésultatsResults
Claims
1. Composition de coloration des fibres kératiniques comprenant, dans un milieu approprié pour la teinture des fibres kératiniques : - une ou plusieurs bases d'oxydation choisies parmi le composé de formule (I) ou ses sels d'addition avec un acide,1. Coloring composition of keratinous fibers comprising, in a medium suitable for dyeing keratinous fibers: one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid,
- un ou plusieurs agents nacrants.one or more pearling agents.
2. Composition selon la revendication précédente, caractérisée en ce que la teneur en composé de formule (I) est comprise entre 0,001 à 10 % en poids par rapport au poids total de la composition tinctoriale.2. Composition according to the preceding claim, characterized in that the content of compound of formula (I) is between 0.001 to 10% by weight relative to the total weight of the dye composition.
3. Composition selon l'une quelconque des revendications précédentes, caractérisée en ce que le ou les agents nacrants sont choisis parmi les composés suivants, seuls ou en mélanges : a) les esters de polyols ayant au moins deux atomes de carbone et d'acides gras à chaîne longue, préférentiellement en Ci0-C3O ; b) les esters de monoalcools à chaîne longue en Ci0-C30; c) les éthers d'alcools gras à chaîne longue solides à une température inférieure ou égale à environ 300C ; d) les esters à chaîne longue (Ci0-C30) d'alcanolamides à chaîne longue3. Composition according to any one of the preceding claims, characterized in that the pearlescent agent (s) are chosen from the following compounds, alone or in mixtures: a) polyol esters having at least two carbon atoms and of acids long chain fatty, preferentially C 10 -C 30 ; b) esters of long chain monohydric alcohols C 10 -C 30 ; c) ethers of long chain fatty alcohols which are solid at a temperature of less than or equal to approximately 30 ° C. d) long-chain (C 10 -C 30 ) esters of long chain alkanolamides
e) les alcools gras monochaînes ayant au moins 20 atomes de carbone; f) les composés ayant de 27 à 48 atomes de carbone et comportant un ou deux groupements éther et/ou thioéther ou sulfoxyde ; g) les oxydes de titane enrobés ou non, les micas et les mélanges de mica et d'oxyde de métaux (titane, fer) et/ou de colorants; h) les cyclodextrines.e) single-chain fatty alcohols having at least 20 carbon atoms; f) compounds having from 27 to 48 carbon atoms and having one or two ether and / or thioether or sulfoxide groups; g) coated or uncoated titanium oxides, micas and mixtures of mica and metal oxide (titanium, iron) and / or dyes; h) cyclodextrins.
4. Composition selon la revendication précédente, caractérisée en ce que le ou les agents nacrants sont choisis parmi les mono- ou distéarate d'éthylène glycol, le distéaryléther, l'alcool béhénique, l'oxyde de titane, les micas, les mélanges de mica et d'oxyde de métaux (titane, fer) et/ou de colorants, le 1-(hexadécyloxy)-2-octadécanol, la β-cyclodextrine, ou leurs mélanges.4. Composition according to the preceding claim, characterized in that the pearlescent agent (s) are chosen from ethylene glycol mono- or distearate, distearyl ether, behenic alcohol, titanium oxide, micas, mica and metal oxide (titanium, iron) and / or dyes, 1- (hexadecyloxy) -2-octadecanol, β-cyclodextrin, or mixtures thereof.
5. Composition selon l'une quelconque des revendications précédentes, caractérisée en ce que la teneur en agent(s) nacrant(s) représente de 0,05 à 10 % en poids par rapport au poids de la composition tinctoriale, et de préférence de 0,1 à 5 % en poids.5. Composition according to any one of the preceding claims, characterized in that the content of pearlescent agent (s) represents from 0.05 to 10% by weight relative to the weight of the dye composition, and preferably from 0.1 to 5% by weight.
6. Composition selon l'une quelconque des revendications précédentes, caractérisée en ce qu'elle comprend un ou plusieurs coupleurs.6. Composition according to any one of the preceding claims, characterized in that it comprises one or more couplers.
7. Composition selon l'une quelconque des revendications précédentes, caractérisée en ce que le ou les coupleurs sont choisis parmi les métaphénylènediamines, les méta- aminophénols, les métadiphénols, les coupleurs naphtaléniques, les coupleurs hétérocycliques et leurs sels d'addition.7. Composition according to any one of the preceding claims, characterized in that the coupler or couplers are chosen from meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalenic couplers, heterocyclic couplers and their addition salts.
8. Composition selon l'une quelconque des revendications précédentes, caractérisée en ce qu'elle contient un ou plusieurs bases d'oxydation additionnelles différentes du composé de formule (I) ou de ses sels.8. Composition according to any one of the preceding claims, characterized in that it contains one or more different additional oxidation bases of the compound of formula (I) or its salts.
9. Composition selon la revendication précédente, caractérisée en ce qu'elle contient une ou plusieurs bases d'oxydation additionnelles choisies parmi les ortho- ou para- phénylènediamines, les bases doubles, les ortho- ou para- aminophénols, et les bases hétérocycliques, ainsi que les sels d'addition de ces composés avec un acide.9. Composition according to the preceding claim, characterized in that it contains one or more additional oxidation bases chosen from ortho- or para-phenylenediamines, double bases, ortho- or para-aminophenols, and heterocyclic bases, as well as the addition salts of these compounds with an acid.
10. Composition selon l'une quelconque des revendications précédentes, caractérisée en ce qu'elle contient un ou plusieurs agents oxydants.10. Composition according to any one of the preceding claims, characterized in that it contains one or more oxidizing agents.
11. Composition selon la revendication précédente, caractérisée en ce que l'agent oxydant est choisi parmi le peroxyde d'hydrogène, le peroxyde d'urée, les bromates de métaux alcalins, les persels, les peracides et les enzymes oxydases et de préférence le peroxyde d'hydrogène.11. Composition according to the preceding claim, characterized in that the oxidizing agent is chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts, peracids and oxidase enzymes and preferably the hydrogen peroxide.
12. Procédé de teinture des fibres kératiniques, caractérisé en ce qu'une composition telle que définie dans l'une quelconque des revendications 1 à 9 est appliquée sur les fibres kératiniques, sans agent oxydant. 12. A process for dyeing keratin fibers, characterized in that a composition as defined in any one of claims 1 to 9 is applied to the keratinous fibers, without oxidizing agent.
13. Procédé de teinture des fibres kératiniques, caractérisé en ce qu'une composition telle que définie dans l'une quelconque des revendications 1 à 9 est appliquée sur les fibres kératiniques en présence d'un ou plusieurs agents oxydants.13. A process for dyeing keratinous fibers, characterized in that a composition as defined in any one of claims 1 to 9 is applied to the keratinous fibers in the presence of one or more oxidizing agents.
14. Dispositif à plusieurs compartiments dans lequel un premier compartiment renferme une composition tinctoriale telle que définie dans l'une quelconque des revendications 1 à 9 et un deuxième compartiment renfermant une composition comprenant un ou plusieurs agents oxydants.14. A multi-compartment device in which a first compartment contains a dye composition as defined in any one of claims 1 to 9 and a second compartment containing a composition comprising one or more oxidizing agents.
15. Dispositif à plusieurs compartiments dans lequel un premier compartiment comprend une ou plusieurs bases d'oxydation choisies parmi le composé de formule (I) ou ses sels avec un acide selon la revendication 1 et éventuellement une ou plusieurs bases d'oxydation différentes du composé de formule (I) ou de ses sels et éventuellement un ou plusieurs coupleurs ; un deuxième compartiment renferme une composition renfermant une composition comprenant un ou plusieurs agents nacrants tels que décrits dans l'une quelconque des revendications 1 et 3 à 5, et éventuellement un troisième compartiment renfermant une composition comprenant un ou plusieurs agents oxydants. 15. A multi-compartment device in which a first compartment comprises one or more oxidation bases chosen from the compound of formula (I) or its salts with an acid according to claim 1 and optionally one or more different oxidation bases of the compound of formula (I) or its salts and optionally one or more couplers; a second compartment contains a composition containing a composition comprising one or more pearlescent agents as described in any one of claims 1 and 3 to 5, and optionally a third compartment containing a composition comprising one or more oxidizing agents.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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FR0953327A FR2945734B1 (en) | 2009-05-19 | 2009-05-19 | TINCTORIAL COMPOSITON COMPRISING THE PARA-PHENYLENE DIAMINE SECONDARY OXIDATION BASE AND A NACRANT AGENT. |
FR0953327 | 2009-05-19 |
Publications (1)
Publication Number | Publication Date |
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WO2010133805A1 true WO2010133805A1 (en) | 2010-11-25 |
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Family Applications (1)
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PCT/FR2010/050966 WO2010133805A1 (en) | 2009-05-19 | 2010-05-19 | Dyeing composition containing a secondary para-phenylenediamine oxidation base and a pearling agent |
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FR (1) | FR2945734B1 (en) |
WO (1) | WO2010133805A1 (en) |
Cited By (9)
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US8663341B2 (en) | 2012-06-25 | 2014-03-04 | The Procter & Gamble Company | Hair colorant compositions comprising 2-Methoxymethy1-1,4-diaminobenzene, methods, and kits comprising the compositions |
US9012691B2 (en) | 2012-10-26 | 2015-04-21 | The Procter & Gamble Company | Process for preparing primary intermediates for dyeing keratin fibers |
US9309185B2 (en) | 2012-10-26 | 2016-04-12 | The Procter & Gamble Company | Process for preparing primary intermediates for dyeing keratin fibers |
US9539192B2 (en) | 2014-04-02 | 2017-01-10 | Noxell Corporation | Hair colouring compositions, kits, method, and use thereof |
US9587116B2 (en) | 2014-11-04 | 2017-03-07 | Noxell Corporation | Azo direct dyes and method for dyeing hair using these dyes |
US9688609B2 (en) | 2014-11-04 | 2017-06-27 | Noxell Corporation | Telescoping synthesis of 2-methoxymethyl-P-phenylenediamine |
US9695109B2 (en) | 2014-11-04 | 2017-07-04 | Noxell Corporation | Telescoping synthesis of 2-methoxymethyl-p-phenylenediamine |
US9758469B2 (en) | 2014-11-04 | 2017-09-12 | Noxell Corporation | Process for the preparation of 2-substituted-1,4-benzenediamines and salts thereof |
CN107249550A (en) * | 2014-12-22 | 2017-10-13 | 斯普瑞格制药股份公司 | Cosmetic sunscreen composition |
Citations (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1026978A (en) | 1962-03-30 | 1966-04-20 | Schwarzkopf Verwaltung G M B H | Method of dyeing hair |
GB1153196A (en) | 1965-07-07 | 1969-05-29 | Schwarzkopf Verwaltung G M B H | Method of Dyeing Hair |
DE2359399A1 (en) | 1973-11-29 | 1975-06-12 | Henkel & Cie Gmbh | Tetraaminopyrimidines as developers in oxidation hair dyes - esp. used with meta aminophenol couplers for blue shading dyes |
EP0055386A2 (en) | 1980-12-13 | 1982-07-07 | Henkel Kommanditgesellschaft auf Aktien | Hair-dyeing preparations |
FR2586913A1 (en) | 1985-09-10 | 1987-03-13 | Oreal | PROCESS FOR FORMING IN IN SITU A COMPOSITION CONSISTING OF TWO PARTS CONDITIONED SEPARATELY AND DISPENSING ASSEMBLY FOR IMPLEMENTING SAID METHOD |
DE3843892A1 (en) | 1988-12-24 | 1990-06-28 | Wella Ag | OXIDATION HAIR AGENTS CONTAINING DIAMINOPYRAZOL DERIVATIVES AND NEW DIAMINOPYRAZOLE DERIVATIVES |
EP0457688A1 (en) | 1990-05-18 | 1991-11-21 | L'oreal | Washing compositions based on silicone and fatty alcohols containing ethers and/or thioethers or sulfoxyde |
DE4127230A1 (en) | 1991-08-16 | 1993-02-18 | Henkel Kgaa | Semi-continuous prodn. of di:alkyl ether(s) - by dehydration of alcohol(s) in presence of sulphonic acids with distn. of water, followed by distn., and re-using acid-contg. fraction |
JPH0563124A (en) | 1991-09-03 | 1993-03-12 | Mitsubishi Electric Corp | Hybrid integrated circuit device |
DE4133957A1 (en) | 1991-10-14 | 1993-04-15 | Wella Ag | HAIR DYE CONTAINING AMINOPYRAZOLE DERIVATIVES AND NEW PYRAZOLE DERIVATIVES |
WO1994008970A1 (en) | 1992-10-16 | 1994-04-28 | Wella Aktiengesellschaft | Oxidation hair dye containing 4,5-diaminopyrazole derivatives and novel 4,5-diaminopyrazole derivatives and process for their production |
WO1994008969A1 (en) | 1992-10-16 | 1994-04-28 | Wella Aktiengesellschaft | Process for producing 4,5-diamino pyrazole derivatives, their use for colouring hair and novel pyrazole derivatives |
WO1996015765A1 (en) | 1994-11-17 | 1996-05-30 | Henkel Kommanditgesellschaft Auf Aktien | Oxidation dyes |
FR2733749A1 (en) | 1995-05-05 | 1996-11-08 | Oreal | COMPOSITIONS FOR DYEING KERATINIC FIBERS CONTAINING DIAMINO PYRAZOLES, DYEING PROCESS, NOVEL DIAMINO PYRAZOLES, AND PREPARATION METHOD THEREOF |
EP0770375A1 (en) | 1995-10-21 | 1997-05-02 | GOLDWELL GmbH | Hair dyeing composition |
DE19543988A1 (en) | 1995-11-25 | 1997-05-28 | Wella Ag | Oxidative hair dye composition |
FR2750048A1 (en) | 1996-06-21 | 1997-12-26 | Oreal | KERATIN FIBER DYEING COMPOSITIONS CONTAINING PYRAZOLO- (1,5-A) -PYRIMIDINE DERIVATIVES, DYEING PROCESS, NOVEL PYRAZOLO- (1,5-A) -PYRIMIDINE DERIVATIVES AND PROCESS FOR PREPARING THE SAME |
EP1428513A1 (en) * | 2002-12-13 | 2004-06-16 | L'oreal | Dyeing composition comprising a tertiary paraphenylenediamine containing a pyrrolidine, and a opacifying or pearlescent agent; method and use |
EP1580184A1 (en) | 2004-02-27 | 2005-09-28 | L'oreal | secondary N-alkylepolyhydroxilated p-phenylendiamines, dye composition comprising them, processes and uses |
FR2870724A1 (en) * | 2004-05-28 | 2005-12-02 | Oreal | Composition, useful for the treatment (e.g. discoloration) of human keratinous material, comprises a compound (ethylenediamine-N,N'-disuccinic acid), pearling agent and/or opacifying agent |
FR2886137A1 (en) | 2005-05-31 | 2006-12-01 | Oreal | Composition useful for coloring of keratinous fibers comprises an oxidation base such as diamino-N,N-dihydropyrazolone derivatives or their salts, a coupling agent and an associative polymer such as polyurethane |
-
2009
- 2009-05-19 FR FR0953327A patent/FR2945734B1/en not_active Expired - Fee Related
-
2010
- 2010-05-19 WO PCT/FR2010/050966 patent/WO2010133805A1/en active Application Filing
Patent Citations (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1026978A (en) | 1962-03-30 | 1966-04-20 | Schwarzkopf Verwaltung G M B H | Method of dyeing hair |
GB1153196A (en) | 1965-07-07 | 1969-05-29 | Schwarzkopf Verwaltung G M B H | Method of Dyeing Hair |
DE2359399A1 (en) | 1973-11-29 | 1975-06-12 | Henkel & Cie Gmbh | Tetraaminopyrimidines as developers in oxidation hair dyes - esp. used with meta aminophenol couplers for blue shading dyes |
EP0055386A2 (en) | 1980-12-13 | 1982-07-07 | Henkel Kommanditgesellschaft auf Aktien | Hair-dyeing preparations |
FR2586913A1 (en) | 1985-09-10 | 1987-03-13 | Oreal | PROCESS FOR FORMING IN IN SITU A COMPOSITION CONSISTING OF TWO PARTS CONDITIONED SEPARATELY AND DISPENSING ASSEMBLY FOR IMPLEMENTING SAID METHOD |
DE3843892A1 (en) | 1988-12-24 | 1990-06-28 | Wella Ag | OXIDATION HAIR AGENTS CONTAINING DIAMINOPYRAZOL DERIVATIVES AND NEW DIAMINOPYRAZOLE DERIVATIVES |
EP0457688A1 (en) | 1990-05-18 | 1991-11-21 | L'oreal | Washing compositions based on silicone and fatty alcohols containing ethers and/or thioethers or sulfoxyde |
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WO1994008970A1 (en) | 1992-10-16 | 1994-04-28 | Wella Aktiengesellschaft | Oxidation hair dye containing 4,5-diaminopyrazole derivatives and novel 4,5-diaminopyrazole derivatives and process for their production |
WO1994008969A1 (en) | 1992-10-16 | 1994-04-28 | Wella Aktiengesellschaft | Process for producing 4,5-diamino pyrazole derivatives, their use for colouring hair and novel pyrazole derivatives |
WO1996015765A1 (en) | 1994-11-17 | 1996-05-30 | Henkel Kommanditgesellschaft Auf Aktien | Oxidation dyes |
FR2733749A1 (en) | 1995-05-05 | 1996-11-08 | Oreal | COMPOSITIONS FOR DYEING KERATINIC FIBERS CONTAINING DIAMINO PYRAZOLES, DYEING PROCESS, NOVEL DIAMINO PYRAZOLES, AND PREPARATION METHOD THEREOF |
EP0770375A1 (en) | 1995-10-21 | 1997-05-02 | GOLDWELL GmbH | Hair dyeing composition |
DE19543988A1 (en) | 1995-11-25 | 1997-05-28 | Wella Ag | Oxidative hair dye composition |
FR2750048A1 (en) | 1996-06-21 | 1997-12-26 | Oreal | KERATIN FIBER DYEING COMPOSITIONS CONTAINING PYRAZOLO- (1,5-A) -PYRIMIDINE DERIVATIVES, DYEING PROCESS, NOVEL PYRAZOLO- (1,5-A) -PYRIMIDINE DERIVATIVES AND PROCESS FOR PREPARING THE SAME |
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US9012691B2 (en) | 2012-10-26 | 2015-04-21 | The Procter & Gamble Company | Process for preparing primary intermediates for dyeing keratin fibers |
US9309185B2 (en) | 2012-10-26 | 2016-04-12 | The Procter & Gamble Company | Process for preparing primary intermediates for dyeing keratin fibers |
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CN107249550A (en) * | 2014-12-22 | 2017-10-13 | 斯普瑞格制药股份公司 | Cosmetic sunscreen composition |
Also Published As
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FR2945734A1 (en) | 2010-11-26 |
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