WO2012146527A2 - Composition de coloration mettant en oeuvre un coupleur 2-hydroxynaphtalénique et une base hétérocyclique en milieu riche en corps gras, le procédé de coloration et le dispositif - Google Patents
Composition de coloration mettant en oeuvre un coupleur 2-hydroxynaphtalénique et une base hétérocyclique en milieu riche en corps gras, le procédé de coloration et le dispositif Download PDFInfo
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/31—Hydrocarbons
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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
- A61K8/34—Alcohols
- A61K8/347—Phenols
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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
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
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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
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/88—Two- or multipart kits
Definitions
- the present invention relates to a composition for dyeing keratin fibres, comprising one or more fatty substances and one or more surfactants, one or more heterocyclic oxidation bases and one or more couplers, of which at least one coupler is a 1 - hydroxynaphthalene derivative, one or more basifying agents, and optionally one or more chemical oxidizing agents, the content of fatty substances in the composition representing in total at least 25% by weight relative to the total weight of the composition.
- the present invention also relates to a dyeing process using this composition, and to a multi-compartment device that is suitable for using this composition. Many people have sought for a long time to modify the colour of their hair and in particular to mask their grey hair.
- One of the dyeing methods is "permanent" or oxidation dyeing, which uses dye compositions containing oxidation dye precursors, generally known as oxidation bases. These oxidation bases are colourless or weakly coloured compounds, which, when combined with oxidizing products, may give rise to coloured compounds by a process of oxidative condensation.
- oxidation bases may be varied by combining them with couplers or coloration modifiers, the latter being chosen especially from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as indole compounds.
- couplers or coloration modifiers the latter being chosen especially from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as indole compounds.
- direct dyes are coloured and colouring molecules that have affinity for fibres. Examples that may be mentioned include benzenic, anthraquinone, nitropyridine, azo, xanthene, acridine, azine and triarylmethane direct dyes.
- Permanent dyeing processes thus consist in using, with the dye composition, an aqueous composition comprising at least one oxidizing agent, under alkaline pH conditions in the vast majority of cases.
- the role of this oxidizing agent is, at least partly, to degrade the melanin of the hair, which, depending on the nature of the oxidizing agent present, leads to more or less pronounced lightening of the fibres.
- the oxidizing agent used is generally hydrogen peroxide.
- the basifying agent makes it possible to adjust the pH of the composition to an alkaline pH to enable activation of the oxidizing agent.
- this basifying agent causes swelling of the keratin fibre, with raising of the scales, which promotes the penetration of the oxidizing agent, and also of the dyes, if they are present, essentially oxidation dyes, into the fibre, and thus increases the efficacy of the dyeing or lightening reaction.
- basifying agents and especially aqueous ammonia, cause the user discomfort due to their strong characteristic odour.
- One of the objects of the present invention is to propose compositions for dyeing human keratin fibres such as the hair that do not have the drawbacks of the existing compositions.
- composition according to the invention in the presence of a chemical oxidizing agent, produces satisfactory colours especially in terms of coverage or colour build-up at the root of the hairs, which makes it possible to avoid a "root" effect of the coloration.
- the invention makes it possible to achieve substantial degrees of lightening while at the same time colouring, without using persalts or increasing the amount of chemical oxidizing agent or of basifying agent.
- composition for dyeing keratin fibres in particular human keratin fibres such as the hair, comprising:
- - f optionally one or more chemical oxidizing agents; and the content of fatty substances representing in total at least 25% by weight relative to the total weight of the formulation.
- a subject of the invention is also dyeing processes using the composition of the invention containing at least one chemical oxidizing agent, and a multi-compartment device for using the composition of the invention.
- the use of the dye composition according to the invention especially in the presence of a chemical oxidizing agent leads to strong, chromatic and/or sparingly selective colorations, i.e. colorations that are uniform along the fibre.
- the dyeing process of the invention also makes it possible particularly to cover keratin fibres at their root, especially down to three centimetres from the base of the said fibres. Furthermore, the colours obtained after treating the fibres remain stable, in particular towards light.
- the invention also makes it possible to reduce the amounts of active agents of the invention such as the dyes and/or basifying agents and/or oxidizing agents.
- the processes according to the invention use formulations that are less malodorous during their application to the hair or during their preparation.
- the human keratin fibres treated via the process according to the invention are preferably the hair.
- composition of the invention comprises a) one or more fatty substances.
- fatty substance means an organic compound that is insoluble in water at ordinary temperature (25°C) and at atmospheric pressure (760 mmHg) (solubility of less than 5%, preferably 1 % and even more preferentially 0.1 %). They have in their structure at least one hydrocarbon-based chain comprising at least 6 carbon atoms or a sequence of at least two siloxane groups.
- the fatty substances are generally soluble in organic solvents under the same temperature and pressure conditions, for instance chloroform, dichloromethane, carbon tetrachloride, ethanol, benzene, toluene, tetrahydrofuran (THF), liquid petroleum jelly or decamethylcyclopentasiloxane.
- the fatty substances of the invention do not contain any salified or unsalified carboxylic acid groups (COOH or COO " ).
- the fatty substances of the invention are neither polyoxyalkylenated nor polyglycerolated.
- oil means a "fatty substance” that is liquid at room temperature (25°C) and at atmospheric pressure (760 mmHg).
- non-silicone ⁇ means an oil not containing any silicon atoms (Si) and the term "silicone o;T means an oil containing at least one silicon atom.
- the fatty substance(s) are chosen from C 6 -Ci 6 alkanes, nonsilicone oils of animal, plant, mineral or synthetic origin, fatty alcohols, esters of a fatty acid and/or of a fatty alcohol, nonsilicone waxes and silicones.
- fatty alcohols, esters and acids more particularly have at least one linear or branched, saturated or unsaturated hydrocarbon-based group comprising 6 to 30 carbon atoms, which is optionally substituted, in particular with one or more hydroxyl groups (in particular 1 to 4). If they are unsaturated, these compounds may have one to three conjugated or non-conjugated carbon-carbon double bonds.
- C 6 -Ci 6 alkanes they are linear or branched, and possibly cyclic.
- Examples that may be mentioned include hexane, dodecane and isoparaffins such as isohexadecane and isodecane.
- oils of animal, plant, mineral or synthetic origin that may be used in the composition of the invention, examples that may be mentioned include:
- oils of plant or synthetic origin such as liquid fatty acid triglycerides containing from 6 to 30 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, for example, sunflower oil, corn oil, soybean oil, marrow oil, grapeseed oil, sesame seed oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, capryiic/capric acid triglycerides, for instance those sold by the company Stearineries Dubois or those sold under the names Miglyol ® 810, 812 and 818 by the company Dynamit Nobel, jojoba oil and shea butter oil.
- liquid fatty acid triglycerides containing from 6 to 30 carbon atoms for instance heptanoic or octanoic acid triglycerides
- sunflower oil corn oil, soybean oil, marrow oil, grapeseed oil, sesame seed oil,
- fluoro oils for instance perfluoromethylcyclopentane and perfluoro-1 ,3- dimethylcyclohexane, sold under the names Flutec ® PC1 and Flutec ® PC3 by the company BN FL Fluorochemicals; perfluoro-1 ,2-dimethylcyclobutane; perfluoroalkanes such as dodecafluoropentane and tetradecafluorohexane, sold under the names PF 5050 ® and PF 5060 ® by the company 3M, or bromoperfluorooctyl sold under the name Foralkyl ® by the company Atochem; nonafluoromethoxybutane and nonafluoroethoxyisobutane; perfluoromorpholine derivatives such as 4-trifluoromethyl perfluoromorpholine sold under the name PF 5052 ® by the company 3M.
- the fatty alcohols that are suitable for use in the invention are more particularly chosen from linear or branched, saturated or unsaturated alcohols comprising from 6 to 30 carbon atoms and preferably from 8 to 30 carbon atoms. Examples that may be mentioned include cetyl alcohol, stearyl alcohol and the mixture thereof (cetylstearyl alcohol), octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol and linoleyl alcohol.
- esters of a fatty acid and/or of a fatty alcohol which are advantageously different than the triglycerides mentioned above, mention may be made especially of esters of saturated or unsaturated, linear or branched Ci-C 2 6 aliphatic mono- or polyacids and of saturated or unsaturated, linear or branched C 1 -C26 aliphatic mono- or polyalcohols, the total carbon number of the esters being greater than or equal to 6 and more advantageously greater than or equal to 10.
- dihydroabietyl behenate octyldodecyl behenate; isocetyl behenate; cetyl lactate; C 12 -C15 alkyl lactate; isostearyl lactate; lauryl lactate; linoleyl lactate; oleyl lactate; (iso)stearyl octanoate; isocetyl octanoate; octyl octanoate; cetyl octanoate; decyl oleate; isocetyl isostearate; isocetyl laurate; isocetyl stearate; isodecyl octanoate; isodecyl oleate; isononyl isononanoate; isostearyl palmitate; methylacetyl ricinoleate; myristyl stearate;
- esters of C4-C 22 dicarboxylic or tricarboxylic acids and of Ci-C 22 alcohols and esters of monocarboxylic, dicarboxylic or tricarboxylic acids and of C 2 -C 2 6 dihydroxy, trihydroxy, tetrahydroxy or pentahydroxy alcohols may also be used.
- esters mentioned above it is preferred to use ethyl, isopropyl, myristyl, cetyl or stearyl palmitate, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, alkyl myristates such as isopropyl, butyl, cetyl or 2-octyldodecyl myristate, hexyl stearate, butyl stearate, isobutyl stearate; dioctyl malate, hexyl laurate, 2-hexyldecyl laurate, isononyl isononanoate or cetyl octanoate.
- alkyl myristates such as isopropyl, butyl, cetyl or 2-octyldodecyl myristate, hexyl stearate, butyl stearate, isobutyl stearate
- composition may also comprise, as fatty ester, sugar esters and diesters of C 6 - C30 and preferably C12-C22 fatty acids.
- sugar esters and diesters of C 6 - C30 and preferably C12-C22 fatty acids.
- sugar esters oxygen- bearing hydrocarbon-based compounds containing several alcohol functions, with or without aldehyde or ketone functions, and which comprise at least 4 carbon atoms.
- sugars may be monosaccharides, oligosaccharides or polysaccharides.
- suitable sugars include sucrose (or saccharose), glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabinose, xylose and lactose, and derivatives thereof, especially alkyl derivatives, such as methyl derivatives, for instance methylglucose.
- the sugar esters of fatty acids may be chosen especially from the group comprising the esters or mixtures of esters of sugars described previously and of linear or branched, saturated or unsaturated C 6 -C 30 , and preferably C12-C22 fatty acids. If they are unsaturated, these compounds may comprise one to three conjugated or non-conjugated carbon-carbon double bonds.
- esters according to this variant may also be selected from monoesters, diesters, triesters, tetraesters and polyesters, and mixtures thereof.
- esters may be, for example, oleates, laurates, palmitates, myristates, behenates, cocoates, stearates, linoleates, linolenates, caprates and arachidonates, or mixtures thereof such as, especially, oleopalmitate, oleostearate and palmitostearate mixed esters.
- monoesters and diesters and especially sucrose, glucose or methylglucose monooleates or dioleates, stearates, behenates, oleopalmitates, linoleates, linolenates and oleostearates.
- esters or mixtures of esters of sugar and of fatty acid examples include:
- sucrose mono-dipalmito-stearate sold by the company Goldschmidt under the name Tegosoft ® PSE.
- the nonsilicone wax(es) are chosen in particular from carnauba wax, candelilla wax, esparto wax, paraffin wax, ozokerite, plant waxes, such as olive tree wax, rice wax, hydrogenated jojoba wax or absolute flower waxes, such as the blackcurrant blossom essential wax sold by Bertin (France), or animal waxes, such as beeswaxes or modified beeswaxes (cerabellina); other waxes or waxy raw materials that may be used according to the invention are in particular marine waxes, such as that sold by Sophim under the reference M82, polyethylene waxes or polyolefin waxes in general.
- the silicones that may be used in the cosmetic compositions of the present invention are volatile or nonvolatile, cyclic, linear or branched silicones, which are unmodified or modified with organic groups, having a viscosity from 5x10 "6 to 2.5 m 2 /s at 25°C, and preferably 1 x10 "5 to 1 m 2 /s.
- the silicones that may be used in accordance with the invention may be in the form of oils, waxes, resins or gums.
- the silicone is chosen from polydialkylsiloxanes, especially polydimethylsiloxanes (PDMS), and organomodified polysiloxanes comprising at least one functional group chosen from poly(oxyalkylene) groups, amino groups and alkoxy groups.
- PDMS polydimethylsiloxanes
- organomodified polysiloxanes comprising at least one functional group chosen from poly(oxyalkylene) groups, amino groups and alkoxy groups.
- Organopolysiloxanes are defined in greater detail in Walter Noll's "Chemistry and
- the silicones are more particularly chosen from those having a boiling point of between 60°C and 260°C, and even more particularly from:
- cyclic polydialkylsiloxanes containing from 3 to 7 and preferably from 4 to 5 silicon atoms.
- cyclic polydialkylsiloxanes containing from 3 to 7 and preferably from 4 to 5 silicon atoms.
- These are, for example, octamethylcyclotetrasiloxane sold in particular under the name Volatile Silicone ® 7207 by Union Carbide or Silbione ® 70045 V2 by Rhodia, decamethylcyclopentasiloxane sold under the name Volatile Silicone ® 7158 by Union Carbide, and Silbione ® 70045 V5 by Rhodia, and mixtures thereof.
- linear volatile polydialkylsiloxanes containing 2 to 9 silicon atoms and having a viscosity of less than or equal to 5x10 "6 m 2 /s at 25°C.
- An example is decamethyltetrasiloxane sold in particular under the name SH 200 by the company Toray Silicone. Silicones belonging to this category are also described in the article published in Cosmetics and Toiletries, Vol. 91 , Jan. 76, pp. 27-32, Todd & Byers, Volatile Silicone Fluids for Cosmetics.
- Non-volatile polydialkylsiloxanes are preferably used.
- silicones are more particularly chosen from polydialkylsiloxanes, among which mention may be made mainly of polydimethylsiloxanes containing trimethylsilyl end groups.
- the viscosity of the silicones is measured at 25°C according to ASTM standard 445 Appendix C.
- CTFA dimethiconol
- the silicone gums that can be used in accordance with the invention are especially polydialkylsiloxanes and preferably polydimethylsiloxanes with high number-average molecular weights of between 200 000 and 1 000 000, used alone or as a mixture in a solvent.
- This solvent can be chosen from volatile silicones, polydimethylsiloxane (PDMS) oils, polyphenylmethylsiloxane (PPMS) oils, isoparaffins, polyisobutylenes, methylene chloride, pentane, dodecane and tridecane, or mixtures thereof.
- Products that can be used more particularly in accordance with the invention are mixtures such as:
- CTFA dimethiconol
- CFA cyclic polydimethylsiloxane also known as cyclomethicone
- the product SF 1236 is a mixture of a gum SE 30 defined above with a viscosity of 20 m 2 /s and of an oil SF 96 with a viscosity of 5x10 "6 m 2 /s. This product preferably comprises 15% of gum SE 30 and 85% of an oil SF 96.
- organopolysiloxane resins that may be used in accordance with the invention are crosslinked siloxane systems containing the following units:
- R represents an alkyl containing 1 to 16 carbon atoms.
- R denotes a C 1 -C4 lower alkyl group, more particularly methyl.
- organomodified silicones that can be used in accordance with the invention are silicones as defined above and comprising in their structure one or more organofunctional groups attached via a hydrocarbon-based group.
- the organomodified silicones may be polydiarylsiloxanes, especially polydiphenylsiloxanes, and polyalkylarylsiloxanes functionalized with the organofunctional groups mentioned previously.
- the polyalkylarylsiloxanes are chosen particularly from linear and/or branched polydimethyl/methylphenylsiloxanes and polydimethyl/diphenylsiloxanes with a viscosity of from 1 10 "5 to 5x 10 "2 m 2 /s at 25°C.
- examples that may be mentioned include the products sold under the following names:
- silicones of the PK series from Bayer such as the product PK20;
- oils of the SF series from General Electric such as SF 1023, SF 1154, SF 1250 and SF 1265.
- organomodified silicones mention may be made of polyorganosiloxanes comprising:
- C 6 -C 2 4 alkyl groups such as the products known as dimethicone copolyol sold by the company Dow Corning under the name DC 1248 or the oils Silwet ® L 722, L 7500, L 77 and L 711 by the company Union Carbide, and the (Ci2)alkylmethicone copolyol sold by the company Dow Corning under the name Q2 5200;
- substituted or unsubstituted amine groups such as the products sold under the name GP 4 Silicone Fluid and GP 7100 by the company Genesee, or the products sold under the names Q2 8220 and Dow Corning 929 or 939 by the company Dow Corning.
- the substituted amine groups are, in particular, C1-C4 aminoalkyl groups;
- the fatty substance(s) do not comprise any C 2 -C 3 oxyalkylene units or any glycerolated units.
- the fatty substances are chosen from compounds that are liquid or pasty at room temperature (25°C) and at atmospheric pressure.
- the fatty substance is a compound that is liquid at a temperature of 25°C and at atmospheric pressure.
- the fatty substance(s) are advantageously chosen from C 6 -Ci 6 alkanes, nonsilicone oils of plant, mineral or synthetic origin, fatty alcohols, esters of a fatty acid and/or of a fatty alcohol, and silicones, or mixtures thereof.
- the fatty substance(s) are chosen from liquid petroleum jelly, C 6 -Ci 6 alkanes, polydecenes liquid esters of fatty acids and/or of fatty alcohols, and liquid fatty alcohols, or mixtures thereof.
- the fatty substance(s) are chosen from liquid petroleum jelly, C 6 -Ci 6 alkanes and polydecenes.
- the composition according to the invention comprises at least 25% by weight of fatty substance.
- composition according to the invention more particularly has a fatty substance content ranging from 25% to 80% by weight, preferably from 30% to 70% by weight and even more advantageously from 30% to 60% by weight relative to the weight of the composition.
- Surfactants The composition of the invention also comprises b) one or more surfactants.
- the surfactant(s) are chosen from anionic, amphoteric, zwitterionic, cationic and nonionic surfactants, and preferentially nonionic surfactants.
- anionic surfactants that may be used in the composition according to the invention, of alkyl sulfates, alkyl ether sulfates, alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates, alkyl sulfonates, alkylamidesulfonates, alkylarylsulfonates, a-olefin sulfonates, paraffin sulfonates, alkyl sulfosuccinates, alkyl ether sulfosuccinates, alkylamide sulfosuccinates, alkyl sulfoacetates, acylsarcosinates, acylglutamates, alkyl sulfosuccinamates, acylisethionates and N-acyltaurates, polyglycoside polycarboxylic acid and alkyl
- These compounds may be oxyethylenated and then preferably comprise from 1 to 50 ethylene oxide units.
- the salts of C 6 -C 24 alkyl monoesters of polyglycoside-polycarboxylic acids can be selected from C 6 -C 24 alkyl polyglycoside-citrates, C 6 -C 24 alkyl polyglycoside-tartrates and C 6 -C 24 alkyl polyglycoside-sulfosuccinates.
- anionic surfactant(s) When the anionic surfactant(s) are in salt form, they may be chosen from alkali metal salts such as the sodium or potassium salt and preferably the sodium salt, the ammonium salts, the amine salts and in particular amino alcohol salts or the alkaline- earth metal salts such as the magnesium salts.
- alkali metal salts such as the sodium or potassium salt and preferably the sodium salt, the ammonium salts, the amine salts and in particular amino alcohol salts or the alkaline- earth metal salts such as the magnesium salts.
- amino alcohol salts that may especially be mentioned include monoethanolamine, diethanolamine and triethanolamine salts, monoisopropanolamine, diisopropanolamine or triisopropanolamine salts, 2-amino-2-methyl-1-propanol salts, 2- amino-2-methyl-1 ,3-propanediol salts and tris(hydroxymethyl)aminomethane salts.
- Alkali metal or alkaline-earth metal salts and in particular the sodium or magnesium salts are preferably used.
- anionic surfactants use is preferably made of (C6-C24)alkyl sulfates, (C 6 -C 2 4)alkyl ether sulfates comprising from 2 to 50 ethylene oxide units, especially in the form of alkali metal, ammonium, amino alcohol and alkaline-earth metal salts, or a mixture of these compounds.
- (Ci 2 -C 2 o)alkyl sulfates (Ci 2 -C 2 o)alkyl ether sulfates comprising from 2 to 20 ethylene oxide units, especially in the form of alkali metal, ammonium, amino alcohol and alkaline-earth metal salts, or a mixture of these compounds.
- amphoteric or zwitterionic surfactant(s), which are preferably nonsilicone, that may be used in the present invention may especially be derivatives of optionally quaternized aliphatic secondary or tertiary amines, in which derivatives the aliphatic group is a linear or branched chain comprising from 8 to 22 carbon atoms, said amine derivatives containing at least one anionic group, for instance a carboxylate, sulfonate, sulfate, phosphate or phosphonate group.
- R a represents a C 1 0-C30 alkyl or alkenyl group derived from an acid R a COOH preferably present in hydrolysed coconut oil, or a heptyl, nonyl or undecyl group;
- ⁇ R b represents a ⁇ -hydroxyethyl group
- ⁇ R c represents a carboxymethyl group
- ⁇ M + represents a cationic counterion derived from an alkali metal or alkaline- earth metal, such as sodium, an ammonium ion or an ion derived from an organic amine, and
- ⁇ X " represents an organic or inorganic anionic counterion, such as that chosen from halides, acetates, phosphates, nitrates, (CrC 4 )alkyl sulfates, (CrC 4 )alkyl- or (Ci-C4)alkylarylsulfonates, in particular methyl sulfate and ethyl sulfate; or alternatively M + and X " are absent;
- ⁇ B represents the group -CH 2 -CH 2 -0-X'
- ⁇ X' represents the group -CH 2 -C(0)OH, -CH 2 -C(0)OZ', -CH 2 -CH 2 -C(0)OH, -CH 2 -CH 2 -C(0)OZ', or a hydrogen atom;
- ⁇ Y' represents the group -C(0)OH, -C(0)OZ', -CH 2 -CH(OH)-S0 3 H or the group
- ⁇ Z' represents a cationic counterion derived from an alkali metal or alkaline-earth metal, such as sodium, an ammonium ion or an ion derived from an organic amine;
- R a ' represents a Ci 0 -C 3 o alkyl or alkenyl group of an acid R a '-C(0)OH preferably present in coconut oil or in hydrolyzed linseed oil, an alkyl group, especially of Ci 7 and its iso form, or an unsaturated Ci 7 group.
- cocoamphodiacetate sold by the company Rhodia under the trade name Miranol ® C2M Concentrate.
- amphoteric or zwitterionic surfactants mentioned above, use is preferably made of (C 8 -C 20 )alkylbetaines such as cocoylbetaine, and (C 8 - C 20 )alkylamido(C3-C 8 )alkylbetaines such as cocamidopropylbetaine, and mixtures thereof. More preferentially, the amphoteric or zwitterionic surfactant(s) are chosen from cocamidopropylbetaine and cocoylbetaine.
- the cationic surfactant(s) that can be used in the compositions of the present invention comprise, for example, salts of optionally polyoxyalkylenated primary, secondary or tertiary fatty amines, quaternary ammonium salts, and mixtures thereof.
- quaternary ammonium salts examples include:
- R 8 to Rii which may be identical or different, represent a linear or branched aliphatic group comprising from 1 to 30 carbon atoms, or an aromatic group such as aryl or alkylaryl, it being understood that at least one of the groups R 8 to Rn comprises from 8 to 30 carbon atoms and preferably from 12 to 24 carbon atoms; and
- X " represents an organic or inorganic anionic counterion, such as that chosen from halides, acetates, phosphates, nitrates, (Ci-C 4 )alkyl sulfates, (CrC 4 )alkyl- or (Ci-C 4 )alkylarylsulfonates, in particular methyl sulfate and ethyl sulfate.
- the aliphatic groups of R 8 to Rn may also comprise heteroatoms especially such as oxygen, nitrogen, sulfur and halogens.
- the aliphatic groups of Rs to Rn are chosen, for example, from C 1 -C30 alkyl, C 1 -C30 alkoxy, polyoxy(C 2 -C 6 )alkylene, C 1 -C30 alkylamide, (Ci 2 -C 22 )alkylamido(C 2 -C6)alkyl, (C 12 - C 22 )alkylacetate, C 1 -C30 hydroxyalkyl, X " is an anionic counterion chosen from halides, phosphates, acetates, lactates, (Ci-C 4 )alkyl sulfates, and (Ci-C 4 )alkyl- or (Ci- C 4 )alkylarylsulfonates.
- tetraalkylammonium chlorides for instance dialkyldimethylammonium or alkyltrimethylammonium chlorides in which the alkyl group contains approximately from 12 to 22 carbon atoms, in particular behenyltrimethylammonium chloride, distearyldimethylammonium chloride, cetyltrimethylammonium chloride, benzyldimethylstearylammonium chloride, or else, secondly, distearoylethylhydroxyethylmethylammonium methosulfate, dipalmitoylethylhydroxyethylammonium methosulfate or distearoylethylhydroxyethylammonium methosulfate, or else, lastly, palmitylamidopropyltrimethylammonium chloride or stearamidopropyldimethyl(myristyl acetate)ammonium chlor
- ⁇ Ri 2 represents an alkenyl or alkyl group comprising from 8 to 30 carbon atoms, for example fatty acid derivatives of tallow;
- ⁇ Ri3 represents a hydrogen atom, a C1-C4 alkyl group or an alkenyl or alkyl group comprising from 8 to 30 carbon atoms;
- Ri 4 represents a C 1 -C4 alkyl group
- ⁇ Ri 5 represents a hydrogen atom or a C 1 -C4 alkyl group
- ⁇ X " represents an organic or inorganic anionic counterion, such as that chosen from halides, acetates, phosphates, acetates, lactates, (d-C 4 )alkyl sulfates, (Ci- C 4 )alkyl- or (Ci-C 4 )alkylarylsulfonates.
- R12 and Ri3 preferably denote a mixture of alkenyl or alkyl groups comprising from 12 to 21 carbon atoms, for example tallow fatty acid derivatives, R-
- 4 denotes a methyl group
- R-I5 denotes a hydrogen atom.
- Rewoquat® W 75 by the company Rewo;
- R16 denotes an alkyl group comprising from about 16 to 30 carbon atoms, which is optionally hydroxylated and/or interrupted with one or more oxygen atoms;
- Ri7 is chosen from hydrogen, an alkyl group comprising from 1 to 4 carbon atoms or a group -(CH 2 )3-N + (R 16a )(R 17a )(R 18 a), X " ;
- i6a, Ri7a, Ri8a, 18, i9, R20 and R 2 i which may be identical or different, are chosen from hydrogen and an alkyl group comprising from 1 to 4 carbon atoms;
- ⁇ X " which may be identical or different, represents an organic or inorganic anionic counterion, such as that chosen from halides, acetates, phosphates, nitrates, (CrC 4 )alkyl sulfates, (Ci-C 4 )alkyl- or (Ci-C 4 )alkylarylsulfonates, in particular methyl sulfate and ethyl sulfate.
- an organic or inorganic anionic counterion such as that chosen from halides, acetates, phosphates, nitrates, (CrC 4 )alkyl sulfates, (Ci-C 4 )alkyl- or (Ci-C 4 )alkylarylsulfonates, in particular methyl sulfate and ethyl sulfate.
- Such compounds are, for example, Finquat CT-P, sold by the company Finetex (Quaternium 89), and Finquat CT, sold by the company Finetex (Quaternium 75);
- R 22 is chosen from C 1 -C6 alkyl and C 1 -C6 hydroxyalkyl or dihydroxyalkyl groups;
- ⁇ R23 is chosen from:
- ⁇ R25 is chosen from:
- Ci-C 6 hydrocarbon-based groups R 29 - linear or branched, saturated or unsaturated Ci-C 6 hydrocarbon-based groups R 29 ,
- R24, 26 and R28 which may be identical or different, are chosen from linear or branched, saturated or unsaturated C7-C 21 hydrocarbon-based groups;
- ⁇ r, s and t which may be identical or different, are integers ranging from 2 to 6;
- ⁇ y is an integer ranging from 1 to 10;
- ⁇ x and z which may be identical or different, are integers ranging from 0 to 10;
- ⁇ X " represents an organic or inorganic anionic counterion
- the alkyl groups R 22 may be linear or branched, and more particularly linear.
- R 22 denotes a methyl, ethyl, hydroxyethyl or dihydroxypropyl group, and more particularly a methyl or ethyl group.
- the sum x + y + z is from 1 to 10.
- R 2 3 is a hydrocarbon-based group R 2 7, it may be long and may contain from 12 to 22 carbon atoms, or may be short and may contain from 1 to 3 carbon atoms.
- R 25 is a hydrocarbon-based group R 2 9, it preferably contains 1 to 3 carbon atoms.
- R 24 , R 26 and R 28 which may be identical or different, are chosen from linear or branched, saturated or unsaturated Cn-C 2 i hydrocarbon-based groups, and more particularly from linear or branched, saturated or unsaturated C -C 2 i alkyl and alkenyl groups.
- x and z which may be identical or different, are equal to 0 or 1.
- y is equal to 1.
- r, s and t which may be identical or different, are equal to 2 or 3, and even more particularly are equal to 2.
- the anionic counterion X " is preferably a halide, such as chloride, bromide or iodide; a (CrC 4 )alkyl sulfate or a (C C 4 )alkyl- or (Ci-C 4 )alkylaryl-sulfonate.
- a halide such as chloride, bromide or iodide
- a (CrC 4 )alkyl sulfate or a (C C 4 )alkyl- or (Ci-C 4 )alkylaryl-sulfonate it is possible to use methanesulfonate, phosphate, nitrate, tosylate, an anion derived from an organic acid, such as acetate or lactate, or any other anion that is compatible with the ammonium containing an ester function.
- the anionic counterion X " is even more particularly chloride, methyl sulfate or ethyl sulfate.
- R 22 denotes a methyl or ethyl group
- - R 25 is chosen from:
- R24, R26 and R 28 which may be identical or different, are chosen from linear or branched, saturated or unsaturated C13-C17 hydrocarbon-based groups, and more particularly from linear or branched, saturated or unsaturated C13-C17 alkyl and alkenyl groups.
- the hydrocarbon-based radicals are linear.
- acyl groups preferably contain 14 to 18 carbon atoms and are obtained more particularly from a plant oil such as palm oil or sunflower oil. When the compound contains several acyl groups, these groups may be identical or different.
- This esterification is followed by a quaternization by means of an alkylating agent such as an alkyl halide, preferably methyl or ethyl halide, a dialkyl sulfate, preferably methyl or ethyl sulfate, methyl methanesulfonate, methyl para- toluenesulfonate, glycol chlorohydrin or glycerol chlorohydrin.
- an alkylating agent such as an alkyl halide, preferably methyl or ethyl halide, a dialkyl sulfate, preferably methyl or ethyl sulfate, methyl methanesulfonate, methyl para- toluenesulfonate, glycol chlorohydrin or glycerol chlorohydrin.
- Such compounds are sold, for example, under the names Dehyquart® by the company Henkel, Stepanquat® by the company Stepan, Noxamium® by the company Ceca or Rewoquat® WE 18 by the company Rewo-Witco.
- composition according to the invention may contain, for example, a mixture of quaternary ammonium salts of mono-, di- and triesters with a weight majority of diester salts.
- ammonium salts containing at least one ester function that are described in patents US-A-4 874 554 and US-A-4 137 180.
- Use may be made of behenoylhydroxypropyltrimethylammonium chloride sold by KAO under the name Quatarmin BTC 131.
- the ammonium salts containing at least one ester function contain two ester functions.
- cationic surfactants that may be present in the composition according to the invention, it is more particularly preferred to choose cetyltrimethylammonium, behenyltrimethylammonium and dipalmitoylethylhydroxyethylmethylammonium salts, and mixtures thereof, and more particularly behenyltrimethylammonium chloride, cetyltrimethylammonium chloride, and dipalmitoylethylhydroxyethylammonium methosulfate, and mixtures thereof.
- nonionic surfactants that may be used in the composition used according to the invention are described, for example, in the Handbook of Surfactants by M.R. Porter, published by Blackie & Son (Glasgow and London), 1991 , pp. 1 16-178. They are especially chosen from polyethoxylated, polypropoxylated or polyglycerolated alcohols, ⁇ -diols and (Ci_C2o)alkylphenols, containing at least one fatty chain comprising, for example, from 8 to 18 carbon atoms, the number of ethylene oxide and/or propylene oxide groups possibly ranging especially from 2 to 50, and the number of glycerol groups possibly ranging especially from 2 to 30.
- copolymers of ethylene oxide and propylene oxide optionally oxyethylenated fatty acid esters of sorbitan, fatty acid esters of sucrose, polyoxyalkylenated fatty acid esters, optionally oxyalkylenated alkylpolyglycosides, alkylglucoside esters, derivatives of N-alkylglucamine and of N-acylmethylglucamine, aldobionamides and amine oxides.
- the nonionic surfactants are more particularly chosen from monooxyalkylenated or polyoxyalkylenated, monoglycerolated or polyglycerolated nonionic surfactants.
- the oxyalkylene units are more particularly oxyethylene or oxypropylene units, or a combination thereof, preferably oxyethylene units. Examples of oxyalkylenated nonionic surfactants that may be mentioned include:
- esters of saturated or unsaturated, linear or branched C 8 -C 3 o acids and of polyethylene glycols • esters of saturated or unsaturated, linear or branched C 8 -C 3 o acids and of polyethylene glycols;
- the surfactants contain a number of moles of ethylene oxide and/or of propylene oxide of between 1 and 100, preferably between 2 and 50 and preferably between 2 and 30.
- the nonionic surfactants do not comprise any oxypropylene units.
- the oxyalkylenated nonionic surfactants are chosen from oxyethylenated C 8 -C 30 alcohols comprising from 1 to 100 mol of ethylene oxide; polyoxyethylenated esters of linear or branched, saturated or unsaturated C 8 -C 30 acids and of sorbitol comprising from 1 to 100 mol of ethylene oxide.
- monoglycerolated or polyglycerolated nonionic surfactants monoglycerolated or polyglycerolated nonionic surfactants.
- monoglycerolated or polyglycerolated C 8 -C 4 o alcohols are preferably used.
- the monoglycerolated or polyglycerolated C 8 -C 4 o alcohols correspond to the formula (A8) below: R 29 0-[CH 2 -CH(CH 2 OH)-0] m -H (A8)
- ⁇ R29 represents a linear or branched C 8 -C 4 o and preferably C 8 -C 3 o alkyl or alkenyl radical
- ⁇ m represents a number ranging from 1 to 30 and preferably from 1 to 10.
- lauryl alcohol containing 4 mol of glycerol (INCI name: Polyglyceryl-4 Lauryl Ether), lauryl alcohol containing 1 .5 mol of glycerol, oleyl alcohol containing 4 mol of glycerol (I NCI name: Polyglyceryl-4 Oleyl Ether), oleyl alcohol containing 2 mol of glycerol (INCI name: Polyglyceryl-2 Oleyl Ether), cetearyl alcohol containing 2 mol of glycerol, cetearyl alcohol containing 6 mol of glycerol, oleocetyl alcohol containing 6 mol of glycerol, and octadecanol containing 6 mol of glycerol.
- the alcohol of formula (A8) may represent a mixture of alcohols in the same way that the value of m represents a statistical value, which means that, in a commercial product, several species of polyglycerolated fatty alcohols may coexist in the form of a mixture.
- the monoglycerolated or polyglycerolated alcohols it is more particularly preferred to use the C 8 /Ci 0 alcohol containing 1 mol of glycerol, the C10/C12 alcohol containing 1 mol of glycerol and the C12 alcohol containing 1.5 mol of glycerol.
- the surfactant used in the process of the invention in the composition is a monooxyalkylenated or polyoxyalkylenated, particularly monooxyethylenated or polyoxyethylenated, or monooxypropylenated or polyoxypropylenated, nonionic surfactant, or a combination thereof, more particularly monooxyethylenated or polyoxyethylenated.
- the surfactant(s) are chosen from nonionic surfactants and anionic surfactants. More particularly, the surfactant(s) present in the composition are chosen from nonionic surfactants. Even more preferentially, the nonionic surfactants are chosen from polyoxyethylenated sorbitol esters and polyoxyethylenated fatty alcohols, and mixtures thereof.
- the amount of surfactant(s) in the composition preferably ranges from 0.1 % to 50% by weight and better still from 0.5% to 20% by weight relative to the total weight of the composition.
- composition of the invention comprises c) one or more heterocyclic oxidation bases, and the addition salts thereof.
- heterocyclic oxidation bases according to the invention are more particularly chosen from pyridine derivatives, pyrimidine derivatives and pyrazole derivatives, and the addition salts thereof.
- pyridine derivatives that may be mentioned are the compounds described, for example, in patents GB 1 026 978 and GB 1 153 196, for instance 2,5- diaminopyridine, 2-(4-methoxyphenyl)amino-3-aminopyridine and 3,4-diaminopyridine, and the addition salts thereof.
- pyridine oxidation bases that are useful in the dyeing process according to the present invention are the 3-aminopyrazolo[1 ,5-a]pyridine oxidation bases or addition salts thereof described, for example, in patent application FR 2801308.
- Examples that may be mentioned include pyrazolo[1 ,5-a]pyrid-3-ylamine, 2-acetylaminopyrazolo[1 ,5- a]pyrid-3-ylamine, 2-morpholin-4-ylpyrazolo[1 ,5-a]pyrid-3-ylamine, 3-aminopyrazolo[1 ,5- a]pyridine-2-carboxylic acid, 2-methoxypyrazolo[1 ,5-a]pyrid-3-ylamine, (3- aminopyrazolo[1 ,5-a]pyrid-7-yl)methanol, 2-(3-aminopyrazolo[1 ,5-a]pyrid-5-yl)ethanol, 2- (3-aminopyrazolo[1 ,5-a]pyrid-7-yl)ethanol, (3-aminopyrazolo[1 ,5-a]pyrid-2-yl)methanol, 3,6-dia
- pyrimidine derivatives that may be mentioned are the compounds described, for example, in the patents DE 2359399; JP 88-169571 ; JP 05-63124; EP 0770375 or patent application WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4- hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6- diaminopyrimidine, 2,5,6-triaminopyrimidine and their addition salts and their tautomeric forms, when a tautomeric equilibrium exists.
- pyrazole derivatives that may be mentioned are the compounds described in the patents DE 3843892, DE 4133957 and patent applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988, such as 4,5-diamino-1 - methylpyrazole, 4,5-diamino-1-( -hydroxyethyl)pyrazole, 3,4-diaminopyrazole, 4,5- diamino-1-(4'-chlorobenzyl)pyrazole, 4,5-diamino-1 ,3-dimethylpyrazole, 4,5-diamino-3- methyl-1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1 ,3-dimethyl- 5-hydrazinopyrazole, 1-benzyl-4,5-diamino-3-methylpyrazole, 4,5-dia
- a 4,5-diaminopyrazole will preferably be used, and even more preferentially 4,5- diamino-1-( -hydroxyethyl)pyrazole and/or a salt thereof.
- Pyrazole derivatives that may also be mentioned include diamino-N,N-dihydro- pyrazolopyrazolones and especially those described in patent application FR-A-2 886 136, such as the following compounds and the addition salts thereof: 2,3-diamino-6,7- dihydro-1 H,5H-pyrazolo[1 ,2-a]pyrazol-1-one, 2-amino-3-ethylamino-6,7-dihydro-1 H, 5H- pyrazolo[1 ,2-a]pyrazol-1 -one, 2-amino-3-isopropylamino-6,7-dihydro-1 H,5H-pyrazolo[1 ,2- a]pyrazol-1 -one, 2-amino-3-(pyrrolidin-1 -yl)-6,7-dihydro-1 H,5H-pyrazolo[1 ,2-a]pyrazol-1 - one, 4,5-diamin
- the oxidation base(s) each advantageously represent from 0.0001% to 10% by weight relative to the total weight of the composition, and preferably from 0.005% to 5% by weight relative to the total weight of the composition.
- composition of the invention may comprise one or more oxidation bases other than heterocyclic oxidation bases, such as benzene-based bases, and the addition salts thereof.
- oxidation bases according to the invention are particularly chosen from from para-phenylenediamines, bis(phenyl)alkylenediamines, para-aminophenols and ortho- aminophenols, and the addition salts thereof.
- para-phenylenediamines that may be mentioned, for example, are 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, ⁇ , ⁇ -diethyl-para-phenylenediamine, N,N-dipropyl-para- phenylenediamine, 4-amino-N,N-diethyl-3-methylaniline, N,N-bis(P-hydroxyethyl)-para- phenylenediamine, 4-N,N-bis ⁇ -hydroxyethyl)amino-2-methylaniline, 4-N,N-bis( - hydroxy
- para-phenylenediamine para-toluenediamine, 2-isopropyl-para-phenylenediamine, 2- -hydroxyethyl-para- phenylenediamine, 2-p-hydroxyethyloxy-para-phenylenediamine, 2,6-dimethyl-para- phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,3-dimethyl-para- phenylenediamine, N,N-bis(P-hydroxyethyl)-para-phenylenediamine, 2-chloro-para- phenylenediamine and 2-p-acetylaminoethyloxy-para-phenylenediamine, and the addition salts thereof with an acid, are particularly preferred.
- bis(phenyl)alkylenediamines that may be mentioned, for example, are N,N'-bis(P-hydroxyethyl)-N,N'-bis(4'-aminophenyl)-1 ,3-diaminopropanol, N,N'-bis( - hydroxyethyl)-N,N'-bis(4'-aminophenyl)ethylenediamine, N,N'-bis(4- aminophenyl)tetramethylenediamine, N,N'-bis(P-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 and 1 ,8-bis(2,5-diaminophenoxy
- para-aminophenols that may be mentioned, for example, are para- aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-chlorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2- hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-( -hydroxyethylaminomethyl)phenol and 4-amino-2-fluorophenol, and the addition salts thereof with an acid.
- ortho-aminophenols that may be mentioned, for example, are 2- aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol and 5-acetamido-2- aminophenol, and the addition salts thereof.
- the additional oxidation base(s) according to the invention each advantageously represent from 0.0001 % to 10% by weight relative to the total weight of the composition, and preferably from 0.005% to 5% by weight relative to the total weight of the composition.
- the cosmetic composition according to the invention comprises d) one or more 1 - hydroxynaphthalene-based couplers.
- 1-hydroxynaphthalene couplers means couplers comprising a 1 - hydroxynaphthalene unit, in which the hydroxyl group in position 1 is free or blocked with a hydrolysable function.
- 1 -hydroxynaphthalene couplers mention may be made of those of formula (B5) and also salts thereof, optical or geometrical isomers and tautomers thereof, and hydration
- R 1 , R 2 , R 3 , R 4 and R 5 which may be identical or different, represent an atom or a group chosen from:
- halogen such as chlorine or bromine
- NR a R b with R a and R b which may be identical or different, representing a hydrogen atom or a (CrC 8 )alkyl group optionally substituted with a hydroxyl group or a (di)(Ci-C 8 )(alkyl)amino group;
- R a and R b with the nitrogen atom, together form a saturated or partially unsaturated 3- to 10-membered mono- or polycyclic heterocycle containing from 1 to 5 heteroatoms chosen from oxygen, nitrogen, sulfur, sulfoxide S(O) and sulfone S(0) 2 , the heterocycle possibly being substituted with a group (d-C ⁇ alkyl or an oxo group; in particular, the heterocycle is chosen from morpholino, piperidino and piperazino;
- aryl such as phenyl
- heterocycle saturated or partially unsaturated 3- to 10-membered mono- or polycyclic heterocycle containing from 1 to 5 heteroatoms chosen from oxygen, nitrogen, sulfur, sulfoxide S(O) and sulfone S(0) 2 , the heterocycle possibly being substituted with a group (CrC 4 )alkyl or an oxo group; in particular, the heterocycle is chosen from morpholinyl, piperidinyl and piperazinyl; x) aryloxy such as phenoxy;
- M representing a hydrogen atom, a group (CrC 8 )alkyl or a cation derived from an alkali metal, an alkaline-earth metal or an organic cation such as ammonium;
- R 2 and R 3 and/or R 1 and R 5 and/or R 4 and R 5 form, together with the carbon atom to which each is attached, an optionally substituted (hetero)cycle or (hetero)aryl; together preferentially form a benzo group;
- ⁇ R 6 represents a hydrogen atom, a hydrolysable protecting group for the hydroxyl group such as -C(X)-R 7 with X denoting an oxygen or sulfur atom, particularly oxygen, and R 7 denoting a hydrogen atom or a group (C C 8 )alkyl, or alternatively R 6 forms with the radical R 1 located in position 8 a sultone group; R 6 preferentially represents a hydrogen atom.
- the 1 -hydroxynaphthalene coupler(s) of formula (B5) are such that R 1 , R 2 , R 3 , R 4 and R 5 , which may be identical or different, represent a hydrogen atom, a halogen atom such as chlorine preferentially in position 4, a hydroxyl group preferentially in position 3, 4, 5, 6 or 7, (CrC 8 )alkyl preferentially in position 2 or (Ci-Cs)alkoxy preferentially in position 4.
- 1 -hydroxynaphthalene-based coupler(s) of formula (B5) are such that:
- R 2 represents a group (Ci-C 6 )alkyloxy such as methoxy, preferably in position 4; and R 1 , R 3 , R 4 and R 5 represent a hydrogen atom; or alternatively
- R 3 represents a group (C C 6 )alkyl such as methyl, preferably in position 2; and R 1 , R 2 , R 4 and R 5 represent a hydrogen atom; or alternatively
- R 3 represents a halogen atom such as chlorine, preferably in position 4; and R 1 , R 2 , R 4 and R 5 represent a hydrogen atom; or alternatively
- R 4 represents a hydroxyl group, preferably in position 5, 6 or 7; and R 1 , R 2 , R 3 and R 5 represent a hydrogen atom; or alternatively
- R 3 represents a hydroxyl group, preferably in position 3 or 4; and R 1 , R 2 , R 4 and R 5 represent a hydrogen atom; or alternatively
- R 1 , R 2 , R 3 , R 4 and R 5 represent a hydrogen atom.
- the 1-hydroxynaphthalene-based coupler(s) each advantageously represent from 0.0001% to 10% by weight relative to the total weight of the composition, and preferably from 0.005% to 5% by weight relative to the total weight of the composition of the invention.
- composition of the invention may comprise one or more couplers other than 1 - hydroxynaphthalene derivatives.
- non-1 -hydroxynaphthalene-based couplers mention may be made especially of meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers other than 1-hydroxynaphthalene-based couplers, and heterocyclic couplers, and also the addition salts thereof.
- the additional coupler(s) each advantageously represent from 0.0001% to 10% by weight relative to the total weight of the composition, and preferably from 0.005% to 5% by weight relative to the total weight of the composition of the invention.
- addition salts of the oxidation bases and couplers that may be used in the context of the invention are especially chosen from the addition salts with an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
- an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
- composition according to the invention may also comprise one or more direct dyes.
- the latter dyes are more particularly chosen from ionic or nonionic species, preferably cationic or nonionic species.
- These direct dyes may be synthetic or of natural origin.
- Suitable direct dyes include azo dyes; methine dyes; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; phthalocyanine dyes, and natural direct dyes, alone or as mixtures.
- one of the nitrogen or carbon atoms of the sequences may be engaged in a ring.
- the dyes of this family are derived from compounds of the type such as methines, azomethines, mono- and diarylmethanes, indoamines (or diphenylamines), indophenols, indoanilines, carbocyanins, azacarbocyanins and isomers thereof, diazacarbocyanins and isomers thereof, tetraazacarbocyanins and hemicyanins.
- dyes of the carbonyl family examples that may be mentioned include dyes chosen from acridone, benzoquinone, anthraquinone, naphthoquinone, benzanthrone, anthranthrone, pyranthrone, pyrazolanthrone, pyrimidinoanthrone, flavanthrone, idanthrone, flavone, (iso)violanthrone, isoindolinone, benzimidazolone, isoquinolinone, anthrapyridone, pyrazoloquinazolone, perinone, quinacridone, quinophthalone, indigoid, thioindigo, naphthalimide, anthrapyrimidine, diketopyrrolopyrrole and coumarin.
- dyes chosen from acridone benzoquinone, anthraquinone, naphthoquinone, benzanthrone, anthranthrone,
- the dyes of the cyclic azine family mention may be made especially of azine, xanthene, thioxanthene, fluorindine, acridine, (di)oxazine, (di)thiazine and pyronin.
- the nitro(hetero)aromatic dyes are more particularly nitrobenzene or nitropyridine direct dyes.
- cationic or non-cationic compounds optionally comprising one or more metals or metal ions, for instance alkali metals, alkaline-earth metals, zinc and silicon.
- Examples of particularly suitable direct dyes include nitrobenzene dyes; azo direct dyes; azomethine direct dyes; methine direct dyes; azacarbocyanin direct dyes, for instance tetraazacarbocyanins (tetraazapentamethines); quinone and in particular anthraquinone, naphthoquinone or benzoquinone direct dyes; azine direct dyes; xanthene direct dyes; triarylmethane direct dyes; indoamine direct dyes; indigoid direct dyes; phthalocyanine direct dyes, porphyrin direct dyes and natural direct dyes, alone or as mixtures.
- the direct dye(s) more particularly represent from 0.0001 % to 10% by weight and preferably from 0.005% to 5% by weight of the total weight of the composition.
- the basifying agents The composition of the invention also comprises e) one or more basifying agents.
- the basifying agent(s) may be mineral or organic or hybrid.
- the mineral basifying agent(s) are preferably chosen from aqueous ammonia, alkali metal carbonates or bicarbonates such as sodium or potassium carbonates and sodium or potassium bicarbonates, sodium hydroxide or potassium hydroxide, or mixtures thereof.
- the organic basifying agent(s) are preferably chosen from organic amines with a pK b at 25°C of less than 12, preferably less than 10 and even more advantageously less than 6. It should be noted that it is the pK b corresponding to the function of highest basicity.
- the organic amines do not comprise any alkyl or alkenyl fatty chains comprising more than ten carbon atoms.
- the organic basifying agent(s) are chosen, for example, from alkanolamines, oxyethylenated and/or oxypropylenated ethylenediamines, amino acids and the compounds of formula (I) below: N - W - N
- W is a C1-C6 divalent alkylene radical optionally substituted with one or more hydroxyl groups or a Ci-C 6 alkyl radical, and/or optionally interrupted with one or more heteroatoms such as O, or NR U ;
- R x , R y , R z , R t and R u which may be identical or different, represent a hydrogen atom or a C C s alkyl or C C 6 hydroxyalkyl or CrC 6 aminoalkyl radical.
- amines of formula (I) examples include 1 ,3- diaminopropane, 1 ,3-diamino-2-propanol, spermine and spermidine.
- alkanolamine means an organic amine comprising a primary, secondary or tertiary amine function, and one or more linear or branched d-Cs alkyl groups bearing one or more hydroxyl radicals.
- Organic amines chosen from alkanolamines such as monoalkanolamines, dialkanolamines or trialkanolamines comprising one to three identical or different C1-C4 hydroxyalkyl radicals are in particular suitable for performing the invention.
- MAA monoethanolamine
- diethanolamine triethanolamine
- monoisopropanolamine diisopropanolamine
- N- dimethylaminoethanolamine 2-amino-2-methyl-1-propanol
- triisopropanolamine 2-amino- 2-methyl-1 ,3-propanediol
- 3-amino-1 ,2-propanediol 3-dimethylamino-1 ,2-propanediol and tris(hydroxymethylamino)methane.
- amino acids that may be used are of natural or synthetic origin, in their L, D or racemic form, and comprise at least one acid function chosen more particularly from carboxylic acid, sulfonic acid, phosphonic acid or phosphoric acid functions.
- the amino acids may be in neutral or ionic form.
- amino acids that may be used in the present invention, mention may be made especially of aspartic acid, glutamic acid, alanine, arginine, ornithine, citrulline, asparagine, carnitine, cysteine, glutamine, glycine, histidine, lysine, isoleucine, leucine, methionine, N-phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine and valine.
- the amino acids are basic amino acids comprising an additional amine function optionally included in a ring or in a ureido function.
- Such basic amino acids are preferably chosen from those corresponding to formula (II) below:
- R CH,— CH ⁇ in whi II)
- R represents a group chosen from:
- the compounds corresponding to formula (II) are histidine, lysine, arginine, ornithine and citrulline.
- the organic amine may also be chosen from organic amines of heterocyclic type. Besides histidine that has already been mentioned in the amino acids, mention may in particular be made of pyridine, piperidine, imidazole, triazole, tetrazole and benzimidazole.
- the organic amine may also be chosen from amino acid dipeptides.
- amino acid dipeptides that may be used in the present invention, mention may be made especially of carnosine, anserine and baleine.
- the organic amine may also be chosen from compounds comprising a guanidine function.
- amines of this type that may be used in the present invention, besides arginine, which has already been mentioned as an amino acid, mention may be made especially of creatine, creatinine, 1 ,1-dimethylguanidine, 1 ,1-diethylguanidine, glycocyamine, metformin, agmatine, N-amidinoalanine, 3-guanidinopropionic acid, 4- guanidinobutyric acid and 2-([amino(imino)methyl]amino)ethane-1-sulfonic acid.
- Hybrid compounds that may be mentioned include the salts of the amines mentioned previously with acids such as carbonic acid or hydrochloric acid.
- Guanidine carbonate or monoethanolamine hydrochloride may be used in particular.
- the basifying agent(s) present in the composition of the invention are chosen from alkanolamines, amino acids in neutral or ionic form, in particular basic amino acids, and preferably corresponding to those of formula (II). Even more preferentially, the basifying agent(s) are chosen from monoethanolamine (MEA) and basic amino acids, in neutral or ionic form.
- MEA monoethanolamine
- the composition according to the invention has a content of basifying agent(s) ranging from 0.01 % to 30% by weight and preferably from 0.1% to 20% by weight relative to the weight of the composition.
- the composition does not contain any aqueous ammonia or salt thereof, or the process according to the invention does not use any aqueous ammonia or salt thereof as basifying agent.
- the composition comprises aqueous ammonia, or a salt thereof, then the amount of basifying agent(s) other than aqueous ammonia is greater than that of the aqueous ammonia (expressed as NH 3 ).
- the amount of basifying agent(s) other than aqueous ammonia is greater than that of the aqueous ammonia (expressed as NH 3 ).
- composition of the invention may also comprise f) one or more chemical oxidizing agents.
- chemical oxidizing agent means an oxidizing agent other than atmospheric oxygen.
- the composition of the invention contains one or more chemical oxidizing agents.
- the chemical oxidizing agent(s) are chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, peroxygenated salts, for instance persulfates, perborates, peracids and precursors thereof and percarbonates of alkali metals or alkaline-earth metals.
- This oxidizing agent is advantageously formed from hydrogen peroxide especially in aqueous solution (aqueous hydrogen peroxide solution), the concentration of which may range more particularly from 0.1% to 50% by weight, even more preferentially from 0.5% to 20% by weight and better still from 1% to 15% by weight relative to the weight of the composition.
- composition of the invention does not contain any peroxygenated salts.
- Solvent
- composition according to the invention may also comprise one or more organic solvents.
- organic solvents examples include linear or branched C 2 - C 4 alkanols, such as ethanol and isopropanol; glycerol; polyols and polyol ethers, for instance 2-butoxyethanol, propylene glycol, dipropylene glycol, propylene glycol monomethyl ether, diethylene glycol monomethyl ether and monoethyl ether, and also aromatic alcohols or ethers, for instance benzyl alcohol or phenoxyethanol, and mixtures thereof.
- the solvent(s), if they are present, represent a content usually ranging from 1 % to 40% by weight and preferably from 5% to 30% by weight relative to the weight of the composition.
- Other additives include linear or branched C 2 - C 4 alkanols, such as ethanol and isopropanol; glycerol; polyols and polyol ethers, for instance 2-butoxyethanol, propylene glycol, dipropylene glycol, propylene glycol monomethyl
- composition according to the invention may also contain various adjuvants conventionally used in hair dye compositions, such as anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof; mineral thickeners, and in particular fillers such as clays, talc; organic thickeners with, in particular, anionic, cationic, nonionic and amphoteric polymeric associative thickeners; antioxidants; penetrants; sequestrants; fragrances; dispersants; film-forming agents; ceramides; preserving agents; opacifiers.
- adjuvants conventionally used in hair dye compositions, such as anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof; mineral thickeners, and in particular fillers such as clays, talc; organic thickeners with, in particular, anionic, cationic, nonionic and amphoteric polymeric associative thickeners; antioxidants; penetrants; sequestrants;
- the above adjuvants are generally present in an amount for each of them of between 0.01% and 20% by weight relative to the weight of composition.
- composition may especially comprise one or more mineral thickeners chosen from organophilic clays and fumed silicas, or mixtures thereof.
- the organophilic clay may be chosen from montmorillonite, bentonite, hectorite, attapulgite and sepiolite, and mixtures thereof.
- the clay is preferably a bentonite or a hectorite.
- These clays may be modified with a chemical compound chosen from quaternary amines, tertiary amines, amine acetates, imidazolines, amine soaps, fatty sulfates, alkylarylsulfonates and amine oxides, and mixtures thereof.
- Organophilic clays that may be mentioned include quatemium-18 bentonites such as those sold under the names Bentone 3, Bentone 38 and Bentone 38V by the company Rheox, Tixogel VP by the company United Catalyst, Claytone 34, Claytone 40 and Claytone XL by the company Southern Clay; stearalkonium bentonites such as those sold under the names Bentone 27 by the company Rheox, Tixogel LG by the company United Catalyst and Claytone AF and Claytone APA by the company Southern Clay; quaternium- 18/benzalkonium bentonites such as those sold under the names Claytone HT and Claytone PS by the company Southern Clay.
- the fumed silicas may be obtained by high-temperature hydrolysis of a volatile silicon compound in an oxhydric flame, producing a finely divided silica. This process makes it possible especially to obtain hydrophilic silicas having a large number of silanol groups at their surface.
- hydrophilic silicas are sold, for example, under the names Aerosil 130®, Aerosil 200®, Aerosil 255®, Aerosil 300® and Aerosil 380® by the company Degussa, and Cab-O-Sil HS5®, Cab-O-Sil EH5®, Cab-O-Sil LM-130®, Cab-O- Sil MS55® and Cab-O-Sil M-5® by the company Cabot.
- hydrophobic silica is then obtained.
- the hydrophobic groups may be:
- silica thus treated are known as "silica silylate” according to the CTFA (6th Edition, 1995). They are sold, for example, under the references Aerosil R812® by the company Degussa and Cab-O-Sil TS-530® by the company Cabot.
- silica thus treated are known as "silica dimethyl silylate" according to the CTFA (6th Edition, 1995). They are sold, for example, under the references Aerosil R972® and Aerosil R974® by the company Degussa, and Cab-O-Sil TS-610® and Cab-O-Sil TS- 720® by the company Cabot.
- the fumed silica preferably has a particle size that may be nanometric to micrometric, for example ranging from about 5 to 200 nm.
- the composition comprises a hectorite, an organomodified bentonite or an optionally modified fumed silica.
- the mineral thickener represents from 1 % to 30% by weight relative to the weight of the composition.
- composition may also comprise one or more organic thickeners.
- thickeners may be chosen from fatty acid amides (coconut monoethanolamide or diethanolamide, oxyethylenated carboxylic acid monoethanolamide alkyl ether), polymeric thickeners such as cellulose-based thickeners (hydroxyethylcellulose, hydroxypropylcellulose or carboxymethylcellulose), guar gum and derivatives thereof (hydroxypropyl guar), gums of microbial origin (xanthan gum, scleroglucan gum), acrylic acid or acrylamidopropanesulfonic acid crosslinked homopolymers and associative polymers (polymers comprising hydrophilic regions and fatty-chain hydrophobic regions (alkyl or alkenyl containing at least 10 carbon atoms) that are capable, in an aqueous medium, of reversibly combining with each other or with other molecules).
- fatty acid amides coconut monoethanolamide or diethanolamide, oxyethylenated carboxylic acid monoethanolamide alkyl ether
- the organic thickener is chosen from cellulose-based thickeners (hydroxyethylcellulose, hydroxypropylcellulose or carboxymethylcellulose), guar gum and derivatives thereof (hydroxypropyl guar), gums of microbial origin (xanthan gum, scleroglucan gum) and acrylic acid or acrylamidopropanesulfonic acid crosslinked homopolymers, and preferably from cellulose-based thickeners in particular with hydroxyethylcellulose.
- cellulose-based thickeners hydroxyethylcellulose, hydroxypropylcellulose or carboxymethylcellulose
- guar gum and derivatives thereof hydroxypropyl guar
- gums of microbial origin xanthan gum, scleroglucan gum
- acrylic acid or acrylamidopropanesulfonic acid crosslinked homopolymers preferably from cellulose-based thickeners in particular with hydroxyethylcellulose.
- the composition of the invention may be in various forms, for instance a solution, an emulsion (milk or cream) or a gel.
- composition according to the invention comprising ingredients a) to f) as defined previously is applied to wet or dry keratin fibres. It is left in place on the fibres for a time generally of from 1 minute to 1 hour and preferably from 5 minutes to 30 minutes.
- the temperature during the dyeing process is conventionally between room temperature (between 15 and 25°C) and 80°C and preferably between room temperature and 60°C.
- the human keratin fibres are optionally rinsed with water, optionally washed with a shampoo and then rinsed with water, before being dried or left to dry.
- composition according to the invention is generally prepared by mixing at least two compositions.
- composition according to the invention comprising ingredients a) to f) as defined previously is derived from the mixing of two compositions:
- composition (A) comprising c) at least one heterocyclic oxidation base as defined previously; d) at least one 1 -hydroxynaphthalene-based coupler as defined previously and e) at least one basifying agent as defined previously; and
- composition (B) comprising f) at least one chemical oxidizing agent as defined previously,
- compositions (A) and (B) comprises a) at least one fatty substance as defined previously, and b) at least one surfactant as defined previously, it being understood that the fatty substance content of the composition according to the invention resulting from the mixing of compositions (A) + (B) comprises at least 25% fatty substance.
- At least one of the compositions (A) or (B) is aqueous.
- both the compositions (A) and (B) are aqueous.
- aqueous composition means a composition comprising at least 5% water.
- an aqueous formulation comprises more than 10% by weight of water and even more advantageously more than 20% by weight of water.
- Composition (A) is preferably aqueous.
- composition (A) comprises at least 50% of fatty substances and even more preferentially at least 50% of fatty substances that are liquid at room temperature (25°C).
- composition (A) is a direct or inverse emulsion, and preferably a direct emulsion (O W).
- compositions (A) and (B) are preferably mixed together in a weight ratio (A)/(B) ranging from 0.2 to 10 and better still from 0.5 to 2.
- the composition according to the invention comprising ingredients a) to f) as defined previously is derived from the mixing of three compositions, the three compositions being aqueous or at least one of them being anhydrous.
- anhydrous cosmetic composition means a cosmetic composition with a water content of less than 5% by weight, preferably less than 2% by weight and even more preferably less than 1 % by weight relative to the weight of the said composition. It should be noted that the water present in the composition is more particularly "bound water", such as water of crystallization in salts, or traces of water absorbed by the starting materials used in the preparation of the compositions according to the invention.
- the anhydrous composition (A 1 ) preferably comprises a) at least one fatty substance as defined previously and more preferentially at least one liquid fatty substance.
- composition ( ⁇ ') preferably comprises c) at least one heterocyclic oxidation base as defined previously and d) at least one 1-hydroxynaphthalene-based coupler as defined previously.
- composition (C) preferably comprises f) at least one chemical oxidizing agent as defined previously.
- the basifying agent(s) e) as defined previously are included in compositions ( ⁇ ') and/or ( ⁇ ') and preferably solely in composition ( ⁇ ').
- the surfactant(s) as defined previously are included in at least one of the compositions ( ⁇ ') or ( ⁇ ') or (C), these three compositions being such that the fatty substance content of the composition according to the invention resulting from the mixing of the three compositions ( ⁇ ') + ( ⁇ ') + (C) comprises at least 25% fatty substances.
- compositions ( ⁇ '), ( ⁇ ') and (C) are preferably mixed together in a weight ratio [(A')+(B')]/(C) ranging from 0.2 to 10 and more particularly from 0.5 to 2 and in a weight ratio ( ⁇ ')/( ⁇ ') ranging from 0.5 to 10 and preferably from 1 to 5.
- the invention relates to a first multi-compartment device comprising a first compartment containing composition (A) as described above and at least one second compartment containing composition (B) as described above, the compositions of the compartments being intended to be mixed together before application, to give the formulation after mixing according to the invention, provided that the amount of fatty substance in this formulation represents at least 25% by weight relative to the weight of the formulation derived from the mixture of (A) + (B).
- the invention also relates to a second multi-compartment device comprising a first compartment containing composition ( ⁇ ') as described above and a second compartment containing a composition ( ⁇ ') as described above, and a third compartment comprising composition (C) as described above, the compositions of the compartments being intended to be mixed together before application, to give the formulation after mixing according to the invention, provided that the amount of fatty substance in this formulation represents at least 25% by weight relative to the weight of the formulation derived from the mixture of (A) + (B) + (C).
- compositions are prepared, in which the amounts are expressed in grams of active materials.
- Composition A1 is a composition having the following properties:
- Composition B1
- Vitamin C L-ascorbic acid 0.25
- Hydroxyethylcellulose (Natrosol 250 HHR, Aqualon) 3.5
- Coupler 2x10 "2 mol
- the mixture obtained is then applied to hair that is 90% grey.
- the "mixture/lock” bath ratio is 10/1 (g/g).
- the leave-on time is 30 minutes at 27°C.
- the colour build-up (AE Lab *) was evaluated in the CIE L* a* b* system.
- L * represents the intensity of the colour
- a * indicates the green/red colour axis
- b * the blue/yellow colour axis.
- the lower the value of L * the darker or more intense the colour.
- the value of AE Lab * was calculated from the values of L * a * b * according to equation (i) below:
- the locks are fixed onto card supports, one half of the lock being obscured with a card.
- the sample holders are placed in the machine on horizontal plates arranged under a lamp, for 18 hours.
- the light-fastness is evaluated by determining the AE
- igh * was calculated from the values of L * a * b * according to the following equation: AE
- igh t* AE Lab * non-irradiated lock - AE Lab * irradiated lock
- composition according to the invention affords much greater colour build-up AE Lab * on 90% grey hair and thus better colour coverage at the root than that obtained with a prior art composition.
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Abstract
La présente invention a pour objet une composition cosmétique de coloration de fibres kératiniques, en particulier de fibres kératiniques humaines telles que les cheveux, comprenant : a) un ou plusieurs corps gras; b) un ou plusieurs tensioactifs; c) une ou plusieurs bases d'oxydation hétérocycliques; d) un ou plusieurs coupleurs à base de 1-hydroxynaphtalène; e) un ou plusieurs agents basifiants; f) éventuellement un ou plusieurs agents oxydants chimiques; et la teneur en corps gras représentant au total au moins 25% en poids par rapport au poids total de la formulation. La présente invention a également pour objet un procédé mettant en oeuvre cette composition, et un dispositif à plusieurs compartiments permettant la réalisation du procédé.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1153687 | 2011-04-29 | ||
| FR1153687A FR2974503B1 (fr) | 2011-04-29 | 2011-04-29 | Composition de coloration mettant en oeuvre un coupleur 1-hydroxynaphtalenique et une base heterocyclique en milieu riche en corps gras, le procede de coloration et le dispositif |
| US201161483374P | 2011-05-06 | 2011-05-06 | |
| US61/483,374 | 2011-05-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2012146527A2 true WO2012146527A2 (fr) | 2012-11-01 |
| WO2012146527A3 WO2012146527A3 (fr) | 2013-10-24 |
Family
ID=45002983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2012/057180 Ceased WO2012146527A2 (fr) | 2011-04-29 | 2012-04-19 | Composition de coloration mettant en oeuvre un coupleur 2-hydroxynaphtalénique et une base hétérocyclique en milieu riche en corps gras, le procédé de coloration et le dispositif |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR2974503B1 (fr) |
| WO (1) | WO2012146527A2 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3001384A1 (fr) * | 2013-01-29 | 2014-08-01 | Oreal | Composition de teinture mettant en oeuvre au moins un coupleur de type meta-aminophenol dans un milieu comprenant un corps gras, procedes et dispositif |
| US8915973B1 (en) | 2013-10-01 | 2014-12-23 | L'oreal | Agent for altering the color of keratin fibers containing a rheology modifying polymer and a fatty substance in an alkaline cream system |
| US11357714B2 (en) | 2020-07-21 | 2022-06-14 | Chembeau LLC | Diester cosmetic formulations and uses thereof |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8721742B2 (en) | 2012-10-02 | 2014-05-13 | L'oreal | Agent for altering the color of keratin fibers comprising a fatty substance, a rheology modifying polymer, and direct dyes in a liquid emulsion system |
| US8721739B2 (en) | 2012-10-02 | 2014-05-13 | L'oreal | Agent for altering the color of keratin fibers containing a fatty substance and a rheology modifying polymer in an alkaline system |
| US8721741B2 (en) | 2012-10-02 | 2014-05-13 | L'oreal | Agent for altering the color of keratin fibers containing a fatty substance, a rheology modifying polymer, and direct dyes in a cream emulsion system |
| US8721740B2 (en) | 2012-10-02 | 2014-05-13 | L'oreal | Agent for altering the color of keratin fibers containing a fatty substance and a rheology modifying polymer in a neutral to acidic system |
| FR3045357B1 (fr) * | 2015-12-18 | 2019-05-24 | L'oreal | Procede de coloration et/ou d'eclaircissement des matieres keratiniques comprenant des tensioactifs oxyethylenes |
| WO2017103260A1 (fr) * | 2015-12-18 | 2017-06-22 | L'oreal | Composition oxydante pour traiter des matières kératiniques comprenant un corps gras et des tensioactifs oxyalkylénés |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3001384A1 (fr) * | 2013-01-29 | 2014-08-01 | Oreal | Composition de teinture mettant en oeuvre au moins un coupleur de type meta-aminophenol dans un milieu comprenant un corps gras, procedes et dispositif |
| WO2014118231A3 (fr) * | 2013-01-29 | 2014-11-06 | L'oreal | Composition de teinture mettant en oeuvre au moins un coupleur de type méta-aminophénol dans un milieu comprenant un corps gras, procédés et dispositif |
| US8915973B1 (en) | 2013-10-01 | 2014-12-23 | L'oreal | Agent for altering the color of keratin fibers containing a rheology modifying polymer and a fatty substance in an alkaline cream system |
| US11357714B2 (en) | 2020-07-21 | 2022-06-14 | Chembeau LLC | Diester cosmetic formulations and uses thereof |
| US11491092B2 (en) | 2020-07-21 | 2022-11-08 | Chembeau LLC | Hair treatment formulations and uses thereof |
| US11801211B2 (en) | 2020-07-21 | 2023-10-31 | Chembeau LLC | Hair treatment formulations and uses thereof |
| US12214065B2 (en) | 2020-07-21 | 2025-02-04 | Chembeau LLC | Diester cosmetic formulations and uses thereof |
| US12285508B2 (en) | 2020-07-21 | 2025-04-29 | Chembeau LLC | Hair treatment formulations and uses thereof |
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| Publication number | Publication date |
|---|---|
| FR2974503A1 (fr) | 2012-11-02 |
| FR2974503B1 (fr) | 2013-04-12 |
| WO2012146527A3 (fr) | 2013-10-24 |
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