WO2013087631A2 - Composition de coloration d'oxydation comprenant un coupleur particulier dans un milieu riche en corps gras, ainsi que procédés et dispositif adapté à ceux-ci - Google Patents

Composition de coloration d'oxydation comprenant un coupleur particulier dans un milieu riche en corps gras, ainsi que procédés et dispositif adapté à ceux-ci Download PDF

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Publication number
WO2013087631A2
WO2013087631A2 PCT/EP2012/075094 EP2012075094W WO2013087631A2 WO 2013087631 A2 WO2013087631 A2 WO 2013087631A2 EP 2012075094 W EP2012075094 W EP 2012075094W WO 2013087631 A2 WO2013087631 A2 WO 2013087631A2
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compound
composition
dihydro
chosen
perimidine
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PCT/EP2012/075094
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WO2013087631A3 (fr
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Alain Lagrange
Marie MIGNON
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L'oreal
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Publication of WO2013087631A3 publication Critical patent/WO2013087631A3/fr

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/411Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/69Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine
    • A61K8/70Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine containing perfluoro groups, e.g. perfluoroethers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair

Definitions

  • Oxidation dye composition comprising a particular coupler in a medium rich in fatty substances, and processes and device suitable therefor
  • the present invention relates to a composition for the oxidation dyeing o f keratin fibres, in particular o f human keratin fibres such as the hair, comprising at least 25 % by weight, relative to the total weight of the composition, o f one or more fatty substances, one or more surfactants, one or more basifying agents, one or more oxidation bases and one or more particular couplers .
  • the present invention also relates to dyeing processes using this composition in the presence o f at least one chemical oxidizing agent, and to a multi-compartment device suitable for using this composition.
  • the present invention relates to the field o f the dyeing o f keratinous fibres and more particularly to the field of hair dyeing.
  • the first type o f dyeing is "permanent" or oxidation dyeing, which uses dye compositions containing oxidation dye precursors, generally known as oxidation bases. These oxidation bases are co lourless or weakly coloured compounds, which, when combined with oxidizing products, may give rise to coloured compounds via a process of oxidative condensation.
  • oxidation bases may be varied by combining them with couplers or co louration modifiers, the latter being chosen especially from aromatic meta- diamines, meta-aminopheno ls, meta-dipheno ls and certain heterocyclic compounds such as indo le compounds.
  • couplers or co louration modifiers the latter being chosen especially from aromatic meta- diamines, meta-aminopheno ls, meta-dipheno ls and certain heterocyclic compounds such as indo le compounds.
  • couplers or co louration modifiers the latter being chosen especially from aromatic meta- diamines, meta-aminopheno ls, meta-dipheno ls and certain heterocyclic compounds such as indo le compounds.
  • the second type o f dyeing is " semi-permanent" dyeing or direct dyeing, which consists in applying direct dyes to the keratin fibres, the said dyes being coloured and colouring mo lecules that have affinity for the fibres, and then leaving them to take, to allow the mo lecules to penetrate by diffusion to the interior o f the fibre, and then rinsing the fibres .
  • the direct dyes generally used are chosen from nitrobenzene, anthraquinone, nitropyridine, azo , xanthene, acridine, azine and triarylmethane direct dyes .
  • one subj ect o f which is especially a composition for the oxidation dyeing keratin fibres, in particular o f human keratin fibres such as the hair, comprising :
  • p denotes 0 or 1
  • Ri, R 2 , R 3 , R 4 , R 5 , R 6 , R7 and Rs denote, independently of each other, a hydrogen atom; an amino group; a halogen atom; a hydroxyl group; a Ci-Cs alkoxy group; a C 2 -C 5 acylamino group; a group CHO, a linear, branched or cyclic Ci-Cis alkyl or C 2 -Cis alkylene group, one or more carbon atoms possibly being replaced with one or more heteroatoms such as oxygen, sulfur or nitrogen, an aryl group, the alkyl, alkylene or aryl groups possibly being substituted with one or more groups chosen from hydroxyl, nitro, nitrile, cyano, carboxylic acid, Ci-Cis alkyl ester, carbamate, carboxamide, amino, alkylamino, dialkylamino, carboxyl, alkoxy and halogen atoms, C 3 -C 6 cycloal
  • the groups R 7 and Rs may form, with the atom that bears them, a ring optionally comprising one or more heteroatoms, this ring possibly being substituted with a Ci-C 6 alkyl group or a hydroxyl group, or possibly being fused with one or more other rings optionally bearing one or more heteroatoms, one or more carbon atoms of the ring(s) possibly being replaced with one or more carbonyl groups.
  • R 7 may also denote a radical derived from a perimidinyl group of formula (I), thus leading to a dimer; the two perimidinyl groups are then preferably linked via the carbon atoms in position 2,
  • R 7 may denote a linear or branched C1-C10 alkylene chain, one or more carbon atoms possibly being replaced with one or more heteroatoms such as oxygen, sulfur or nitrogen and/or optionally comprising a ring, or alternatively a saturated or unsaturated ring, optionally comprising one or more heteroatoms; a chain comprising several and preferably two saturated or unsaturated rings linked together via a covalent bond or via a heteroatom, the chains or the ring possibly being substituted with a hydroxyl group or with a perimidinyl radical o f formula (I) preferably via the carbon atom in position 2,
  • R 4 when R 4 is in position 7 and R 5 is in position 6, then they can form, together with the carbon atoms that bear them, a 5 - to 8- membered ring optionally comprising one or more heteroatoms .
  • the present invention also relates to dyeing processes using this composition in the presence o f at least one chemical oxidizing agent, and to a multi-compartment device suitable for using this composition.
  • the use o f the composition according to the invention in the presence o f at least one chemical oxidizing agent leads to strong co lorations with little selectivity. Furthermore, the co lorations obtained remain stable, in particular with respect to light.
  • the human keratinous fibres treated by the method according to the invention are preferably the hair.
  • composition according to the invention comprises one or more fatty substances .
  • fatty substance means an organic compound that is inso luble in water at ordinary room temperature (25 °C) and at atmospheric pressure (760 mmHg) (solubility o f less than 5 %, preferably 1 % and even more preferentially 0. 1 %) . They exhibit, in their structure, at least one hydrocarbon chain comprising at least 6 carbon atoms or a sequence o f at least two siloxane groups.
  • the fatty substances are generally so luble in organic so lvents under the same temperature and pressure conditions, for instance chloroform, ethano l, benzene, liquid petrolatum or decamethylcyclopentasiloxane. These fatty substances are neither polyoxyethylenated nor polyglycerolated.
  • the fatty substances are chosen from C 6 - C i 6 hydrocarbons, hydrocarbons containing more than 16 carbon atoms, non-silicone oils o f animal origin, plant oils o f triglyceride type, synthetic triglycerides, fluoro oils, fatty alcoho ls, esters of fatty acids and/or of fatty alcoho ls other than triglycerides, and plant waxes, non- silicone waxes and silicones .
  • the fatty alcoho ls, fatty esters and fatty acids more particularly contain one or more linear or branched, saturated or unsaturated hydrocarbon-based groups comprising 6 to 30 carbon atoms, which are optionally substituted, in particular with one or more (in particular 1 to 4) hydroxyl groups. If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds .
  • C 6 - C i 6 hydrocarbons they are linear or branched, and possibly cyclic, and are preferably alkanes. Examp les that may be mentioned include hexane, dodecane and isoparaffins such as isohexadecane and isodecane.
  • the triglyceride oils o f p lant or synthetic origin are preferably chosen from liquid fatty acid triglycerides containing from 6 to 30 carbon atoms, for instance heptanoic or octanoic acid triglycerides, or alternatively, for examp le, 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, caprylic/capric acid triglycerides, for instance those so ld by the company Stearineries Dubois or those so ld under the names Miglyo l® 8 1 0, 8 12 and 8 1 8 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, or
  • the linear or branched hydrocarbons o f mineral or synthetic origin containing more than 16 carbon atoms are preferably chosen from liquid paraffins, petroleum j elly, liquid petrolatum, polydecenes, and hydrogenated polyisobutene such as Parleam® .
  • the fluoro oils may be chosen from perfluoromethylcyclopentane and perfluoro- 1 ,3 -dimethylcyclohexane, so ld under the names Flutec ® PC I and Flutec ® PC3 by the company BNFL Fluorochemicals; perfluoro- 1 ,2-dimethylcyclobutane; perfluoroalkanes such as dodecafluoropentane and tetradecafluorohexane, so ld under the names PF 5050 ® and PF 5060 ® by the company 3M, or bromoperfluorooctyl so ld 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 alcoho ls that may be used in the composition according to the invention are saturated or unsaturated, and linear or branched, and comprise from 6 to 30 carbon atoms and more particularly from 8 to 30 carbon atoms.
  • Examples that may be mentioned include cetyl alcoho l, stearyl alcoho l and the mixture thereo f (cetylstearyl alcoho l), octyldodecanol, 2-butyloctanol, 2- hexyldecanol, 2-undecylpentadecanol, oleyl alcoho l and lino leyl alcoho l.
  • the wax(es) that may be used in the composition are chosen especially from carnauba wax, candelilla wax, esparto grass wax, paraffin wax, ozokerite, plant waxes, for instance olive wax, rice wax, hydrogenated jojoba wax or the absolute waxes o f flowers such as the essential wax o f blackcurrant blo ssom sold by the company Bertin (France), animal waxes, for instance beeswaxes, or modified beeswaxes (cerabellina); other waxes or waxy starting materials that may be used according to the invention are especially marine waxes such as the product sold by the company Sophim under the reference M82, and polyethylene waxes or polyo lefin waxes in general.
  • the fatty acids that may be used in the composition may be saturated or unsaturated and contain from 6 to 30 carbon atoms and in particular from 9 to 30 carbon atoms. They are more particularly chosen from myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, linolenic acid and isostearic acid.
  • esters o f a fatty acid and/or of a fatty alcoho l, which are advantageously different from the triglycerides mentioned above, mention may be made especially o f esters o f saturated or unsaturated, linear or branched C i -C 26 aliphatic mono- or polyacids and o f saturated or unsaturated, linear or branched C i -C 26 aliphatic mono- or polyalcoho ls, the total carbon number o f the esters more particularly being greater than or equal to 1 0.
  • esters of C 4 -C 22 dicarboxylic or tricarboxylic acids and of C i -C 22 alcoho ls and esters of monocarboxylic, dicarboxylic or tricarboxylic acids and o f C 2 -C 26 dihydroxy, trihydroxy, tetrahydroxy or pentahydroxy alcoho ls 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; dio ctyl malate, hexyl laurate, 2-hexyldecyl laurate, isononyl isononanoate or cetyl octanoate.
  • the composition may also comprise, as fatty ester, sugar esters and diesters of C6 - C30 and preferably C 12 - C22 fatty acids .
  • sugar means oxygen-bearing hydrocarbon-based compounds bearing several alcoho l functions, with or without aldehyde or ketone functions, and which comprise at least 4 carbon atoms. These sugars can be monosaccharides, oligosaccharides or polysaccharides .
  • sugars for example, o f sucrose (or saccharose), glucose, galactose, ribose, fucose, maltose, fructose, mannose, arabino se, xylose, lactose and their derivatives, in particular alkyl derivatives, such as methyl derivatives, for example methylglucose.
  • esters o f sugars and o f fatty acids can be chosen in particular from the group consisting of the esters or mixtures of esters of sugars described above and of saturated or unsaturated and linear or branched C6 - C30 and preferably C 12 - C22 fatty acids. If they are unsaturated, these compounds may comprise one to three conjugated or unconjugated carbon-carbon double bonds .
  • esters according to this alternative form can also be chosen from mono-, di-, tri- and tetraesters and polyesters, and mixtures thereof. These esters can, for example, be o leates, laurates, palmitates, myristates, behenates, cocoates, stearates, lino leates, lino lenates, caprates, arachidonates or their mixtures, such as, in particular, oleate/palmitate, oleate/stearate or palmitate/stearate mixed esters .
  • Examples o f esters or mixtures o f esters of sugar and o f fatty acid that may also be mentioned include :
  • Ryoto Sugar Esters for example referenced B370 and corresponding to sucrose behenate formed of 20% monoester and 80% diester, triester and polyester;
  • the silicones that can be used in the composition of the present invention are vo latile or non- vo latile, cyclic, linear or branched silicones, which are unmodified or mo dified with organic groups, having a viscosity from 5 x 10 "6 to 2.5 m 2 /s at 25 °C, and preferably l x l O "5 to 1 m 2 /s .
  • the silicones which can be used in accordance with the invention can be provided in the form of oils, waxes, resins or gums .
  • the silicone is chosen from polydialkylsiloxanes, in particular polydimethylsiloxanes (PDMSs), and organomodified polysiloxanes comprising at least one functional group chosen from poly(oxyalkylene) groups, amino groups and alkoxy groups.
  • PDMSs 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 Technology of Silicones (1968), Academic Press. They may be volatile or non-volatile.
  • the silicones are more particularly chosen from those with 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. They 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 5 x 10 "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 .
  • Use is preferably made of non-volatile polydialkylsiloxanes, polydialkylsiloxane gums and resins, polyorganosiloxanes modified with the organofunctional groups above, and mixtures thereof.
  • silicones are more particularly chosen from polydialkylsiloxanes, among which mention may be made mainly of polydimethylsiloxanes having trimethylsilyl end groups.
  • the viscosity of the silicones is measured at 25°C according to ASTM standard 445 Appendix C.
  • oils of the 200 series from Dow Corning such as DC200 having a viscosity of 60000 mm 2 /s;
  • CTFA dimethiconol
  • the silicone gums which can be used in accordance with the invention are in particular polydialkylsiloxanes and preferably polydimethylsiloxanes having high number-average molecular weights of between 200000 and 1 000000, 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, tridecane or their mixtures .
  • Products which can be used more particularly in accordance with the invention are mixtures, such as :
  • CTFA dimethicono l
  • CFA cyclic polydimethylsiloxane
  • this product is an SF 30 gum corresponding to a dimethicone, having a number-average mo lecular weight o f 500 000, dissolved in the oil SF 1202 Silicone Fluid corresponding to decamethy Icy clop entasiloxane;
  • the product SF 1236 is the mixture of a gum SE 30 defined above having a viscosity o f 20 m 2 /s and of an oil
  • This product preferably comprises 15 % of gum SE 30 and 85 % of an oil SF 96.
  • organopolysiloxane resins that can be used in accordance with the invention are crosslinked siloxane systems containing the fo llowing units :
  • R represents an alkyl containing 1 to 16 carbon atoms.
  • R denotes a C i -C 4 lower alkyl group, more particularly methyl.
  • Silicone Fluid S S 4230 and S S 4267 by General Electric which are silicones of dimethyl/trimethylsiloxane structure.
  • 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 can be polydiarylsiloxanes, in particular polydiphenylsiloxanes, and polyalkylarylsiloxanes functionalized by the abovementioned organofunctional groups.
  • the polyalkylarylsiloxanes are chosen particularly from linear and/or branched polydimethyl/methylphenylsiloxanes and polydimethyl/diphenylsiloxanes with a viscosity of from lxlO "5 to 5xl0 "2 m 2 /s at 25°C.
  • oils of the SF series from General Electric such as SF 1023, SF 1154, SF 1250 and SF 1265.
  • organomodified silicones of polyorganosiloxanes comprising:
  • polyethyleneoxy and/or polypropyleneoxy groups optionally comprising C6-C 2 4 alkyl groups, such as the products named dimethicone copolyol sold by Dow Corning under the name DC 1248 or the oils Silwet ® L 722, L 7500, L 77 and L 711 by Union Carbide, and the (Ci 2 )alkyl methicone copolyol sold by Dow Corning under the name Q25200;
  • substituted or unsubstituted amino groups such as the products sold under the names GP 4 Silicone Fluid and GP 7100 by Genesee or the products sold under the names Q2 8220 and Dow Corning 929 or 939 by Dow Corning.
  • the substituted amino groups are in particular C 1 - C 4 aminoalkyl groups;
  • the fatty substances are chosen from compounds that are liquid or pasty at room temperature and at atmospheric pressure.
  • the fatty substance is a compound which is liquid at the temperature of 25 °C and at atmospheric pressure.
  • the fatty substances are advantageously chosen from C 6 - C i 6 hydrocarbons, hydrocarbons containing more than 16 carbon atoms, non-silicone oils o f animal origin, plant oils o f triglyceride type, synthetic triglycerides, fluoro oils, fatty alcoho ls, esters of fatty acids and/or of fatty alcoho ls other than triglycerides, and plant waxes, non- silicone waxes and silicones, and a mixture thereof.
  • the fatty substance(s) are chosen from liquid petrolatum, polydecenes, fatty alcoho ls and liquid esters o f a fatty acid and/or of a fatty alcohol, or mixtures thereof.
  • the fatty substances are chosen from liquid petrolatum and octyldodecanol.
  • the composition according to the invention has a fatty substance content of at least 25 % by weight. More particularly, the fatty substance concentration ranges 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 total weight o f the composition.
  • composition according to the invention also comprises one or more surfactants .
  • the surfactant(s) are chosen from anionic, amphoteric, zwitterionic, cationic and nonionic surfactants, and preferentially nonionic surfactants .
  • anionic surfactant means a surfactant comprising, as ionic or ionizable groups, only anionic groups.
  • alkyl sulfates alkyl ether sulfates, alkylamido ether sulfates, alkylaryl polyether sulfates, monoglyceride sulfates, alkylsulfonates, alkylamidesulfonates, alkylarylsulfonates, a-o lefin sulfonates, paraffin sulfonates, alkyl sulfo succinates, alkyl ether sulfo succinates, alkylamide sulfo succinates, alkyl sulfoacetates, acylsarcosinates, acylglutamates, alkyl sulfosuccinamates, acylisethionates and N- acyltaurates, polyglycoside polycarboxylic acid and alkyl monoester
  • These compounds can be oxyethylenated and then preferably comprise from 1 to 50 ethylene oxide units.
  • the salts o f C 6 -C 2 4 alkyl monoesters o f polyglycoside- polycarboxylic acids can be chosen from C 6 -C 2 4 alkyl polyglycoside- citrates, C 6 -C 2 4 alkyl polyglycoside-tartrates and C 6 -C 2 4 alkyl poly glycoside-sulfo succinates .
  • the anionic surfactant(s) When the anionic surfactant(s) are in salt form, it (they) may be chosen from alkali metal salts such as the sodium or potassium salt and preferably the sodium salt, ammonium salts, amine salts and in particular amino alcoho l salts, or alkaline earth metal salts such as the magnesium salts .
  • alkali metal salts such as the sodium or potassium salt and preferably the sodium salt, ammonium salts, amine salts and in particular amino alcoho l salts, or alkaline earth metal salts such as the magnesium salts .
  • alkali metal salts such as the sodium or potassium salt and preferably the sodium salt, ammonium salts, amine salts and in particular amino alcoho l salts, or alkaline earth metal salts such as the magnesium salts .
  • amino alcohol salts that may especially be mentioned include monoethanolamine, diethanolamine and triethanolamine salts, monoisopropanolamine, diisopropano
  • Use is preferably made of alkali metal or alkaline earth metal salts and in particular of sodium or magnesium salts.
  • Use is preferably made, among the anionic surfactants mentioned, of (C 6 -C 2 4)alkyl sulfates, (C 6 -C 2 4)alkyl ether sulfates comprising from 2 to 50 ethylene oxide units, in particular in the form of alkali metal, ammonium, aminoalcohol and alkaline earth metal salts, or a mixture of these compounds.
  • (Ci 2 -C 2 o)alkyl sulfates it is preferable to use (Ci 2 -C 2 o)alkyl sulfates, (Ci 2 -C 2 o)alkyl ether sulfates comprising from 2 to 20 ethylene oxide units, in particular in the form of alkali metal, ammonium, aminoalcohol and alkaline earth metal salts, or a mixture of these compounds.
  • sodium lauryl ether sulfate comprising 2.2 mol of ethylene oxide.
  • amphoteric or zwitterionic surfactant(s), which are preferably (a) non-silicone surfactant(s), which can be used in the present invention can in particular be derivatives of secondary or tertiary, optionally quaternized aliphatic amines, in which derivatives the aliphatic group is a linear or branched chain comprising from 8 to 22 carbon atoms, said amine derivatives comprising at least one anionic group, such as, for example, a carboxylate, sulfonate, sulfate, phosphate or phosphonate group.
  • Ra represents a C 1 0 - C30 alkyl or alkenyl group derived from an acid RaCOOH preferably present in hydrolysed coconut oil, a heptyl, nonyl group or undecyl group;
  • Rb represents a ⁇ -hydroxyethyl group
  • Rc 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, (C i - C 4 )alkyl sulfates, (C i -C 4 )alkyl- or (C i -C 4 )alkylarylsulfonates, in particular methyl sulfate and ethyl sulfate; or alternatively M + and X " are absent;
  • B represents the group -CH 2 -CH 2 -0-X'
  • X * represents the group -CH 2 -C(0)OH, -CH 2 -C(0)OZ ' , -CH 2 - CH 2 -C(0)OH or -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)- S O 3 H or the group -CH 2 -CH(OH)-S0 3 -Z ' ;
  • 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;
  • Ra' represents a C 1 0 - C30 alkyl or alkenyl group of an acid Ra' - C(0)OH which is preferably present in coconut oil or in hydrolysed linseed oil, or an alkyl group, especially a C 1 7 group , and its iso form, or an unsaturated C 1 7 group .
  • amphoteric or zwitterionic surfactants use is preferably made o f (C 8 - C2o)alkylbetaines such as cocobetaine, and (C 8 - C2o)alkylamido(C 3 -C 8 )alkylbetaines such as cocamidopropylbetaine, and mixtures thereof. More preferably, the amphoteric or zwitterionic surfactant(s) are chosen from cocamidopropyl betaine and coco betaine.
  • the cationic surfactant(s) which can be used in the composition according to the invention comprise, for example, salts of primary, secondary or tertiary fatty amines, which are optionally polyoxyalkylenated, quaternary ammonium salts and mixtures thereof.
  • quaternary ammonium salts examples include :
  • Rs to Rn 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 o f the groups Rs 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, (C i - C 4 )alkyl sulfates, (C i -C 4 )alkyl or (C i -C 4 )alkylaryl sulfonates, in particular methyl sulfate and ethyl sulfate .
  • the aliphatic groups o f Rs 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 C1-C30 alkyl, C1-C30 alkoxy, polyoxy(C2-Ce)alkylene, C1-C30 alkylamide, (Ci2-C22)alkylamido(C2-C6)alkyl, (Ci2-C22)alkylacetate, C1-C30 hydroxyalkyl, X " is an anionic counterion chosen from halides, phosphates, acetates, lactates, (Ci-C4)alkyl sulfates, and (Ci-C4)alkyl- or (Ci-C4)alkylarylsulfonates.
  • quaternary ammonium salts of formula (A3) preference is given firstly to 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 met ho sulfate, dipalmitoylethylhydroxyethylammonium methosulfate or distearoylethylhydroxyethylammonium methosulfate, or else, lastly, palmitylamidopropyltrimethylammonium chloride or stearamidopropyldimethyl(myristyl acetate)ammonium
  • R12 represents an alkenyl or alkyl group comprising from 8 to 30 carbon atoms, for example tallow fatty acid derivatives
  • R represents a hydrogen atom, a C1-C4 alkyl group or an alkenyl or alkyl group comprising from 8 to 30 carbon atoms;
  • Ri4 represents a C1-C4 alkyl group
  • Ri5 represents a hydrogen atom or a C1-C4 alkyl group
  • X " represents an organic or inorganic anionic counterion, such as that chosen from halides, phosphates, acetates, lactates, (Ci- C 4 )alkyl sulfates, (Ci-C 4 )alkyl or (Ci-C 4 )alkylaryl sulfonates.
  • Ri2 and R13 preferably denote a mixture of alkenyl or alkyl groups comprising from 12 to 21 carbon atoms, for example tallow fatty acid derivatives, Ri 4 denotes a methyl group, and R15 denotes a hydrogen atom.
  • a product is sold, for example, under the name Rewoquat® W 75 by the company Rewo;
  • Ri6 denotes an alkyl group comprising approximately from 16 to 30 carbon atoms, which is optionally hydroxylated and/or interrupted by 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 + (Ri6a)(Ri7a)(Ri8a), X " ;
  • Ri6a, Ri7a, Ri8a, Ri8, Ri9, R 2 o and R 2 1 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, (Ci-C 4 )alkyl sulfates, (Ci-C 4 )alkyl or (Ci-C 4 )alkylaryl sulfonates, in particular methyl sulfate and ethyl sulfate.
  • organic or inorganic anionic counterion such as that chosen from halides, acetates, phosphates, nitrates, (Ci-C 4 )alkyl sulfates, (Ci-C 4 )alkyl or (Ci-C 4 )alkylaryl sulfonates, in particular methyl sulfate and ethyl sulfate.
  • Such compounds are, for example, Finquat CT-P, provided by Finetex (Quaternium 89), or Finquat CT, provided by Finetex (Quaternium 75);
  • R22 is chosen from Ci-C 6 alkyl groups and Ci-C 6 hydroxyalkyl or dihydroxyalkyl groups,
  • R23 is chosen from:
  • R25 is chosen from:
  • R24, R26 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, with the proviso that the sum x + y + z is from 1 to 15, that when x is 0, then R23 denotes R27 and that when z is 0, then R25 denotes R29.
  • the alkyl groups R22 may be linear or branched, and more particularly linear.
  • R22 denotes a methyl, ethyl, hydroxyethyl or dihydroxypropyl group, and more particularly a methyl or ethyl group .
  • the sum x + y + z ranges from 1 to 1 0.
  • R23 is a hydrocarbon-based group R27 , 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 .
  • R25 is a hydrocarbon-based group R29 , it preferably contains 1 to 3 carbon atoms .
  • R24 , R26 and R28 which may be identical or different, are chosen from linear or branched, saturated or unsaturated C 1 1 -C 2 1 hydrocarbon-based groups, and more particularly from linear or branched, saturated or unsaturated C n -C 2 1 alkyl and alkenyl groups .
  • x and z which may be identical or different, are preferably 0 or 1 .
  • y is advantageously equal to 1 .
  • r, s and t which may be identical or different, equal 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 (C i - C 4 )alkyl sulfate or a (C i - C 4 )alkylsulfonate or (C i -C 4 )alkylarylsulfonate.
  • a halide such as chloride, bromide or iodide
  • a (C i - C 4 )alkyl sulfate or a (C i - C 4 )alkylsulfonate or (C i -C 4 )alkylarylsulfonate 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.
  • R22 denotes a methyl or ethyl group
  • - R25 is chosen from:
  • R24 , R26 and R28 which may be identical or different, are chosen from linear or branched, saturated or unsaturated C 1 3 -C 1 7 hydrocarbon-based groups, and more particularly from linear or branched, saturated or unsaturated C 1 3 -C 1 7 alkyl and alkenyl groups .
  • hydrocarbon radicals are linear.
  • examples that may be mentioned include salts, especially the chloride or methyl sulfate, of diacyloxyethyldimethyl ammonium,
  • the acyl groups preferably contain 14 to 1 8 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 fo llowed by a quaternization by means of an alkylating agent such as an alkyl halide, preferably methyl or ethyl halide, a dialkyl sulfate, preferably dimethyl or diethyl sulfate, methyl methanesulfonate, methyl /?ara-toluenesulfonate, glycol chlorohydrin or glycerol chlorohydrin.
  • an alkylating agent such as an alkyl halide, preferably methyl or ethyl halide, a dialkyl sulfate, preferably dimethyl or diethyl sulfate, methyl methanesulfonate, methyl /?ara-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 monoesters, diesters 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 dipalmitoylethylhydroxyethylmethyl- ammonium salts, and mixtures thereof, and more particularly behenyltrimethylammonium chloride, cetyltrimethylammonium chloride, and dipalmitoylethylhydroxyethylammonium methosulfate, and mixtures thereof.
  • nonionic surfactants that can 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. 116-178.
  • They are especially chosen from alcohols, a-diols and (Ci-C2o)alkylphenols, these compounds being polyethoxylated, polypropoxylated or polyglycerolated, and containing at least one fatty chain comprising, for example, from 8 to 18 carbon atoms, it being possible for the number of ethylene oxide and/or propylene oxide groups to especially range from 2 to 50, and for the number o f glycerol groups to especially range from 2 to 30.
  • the nonionic surfactants are chosen more particularly from mono- or polyoxyalkylenated or mono- or polyglycero lated nonionic surfactants.
  • the oxyalkylene units are more particularly oxyethylene or oxypropylene units, or their combination, preferably oxyethylene units.
  • Examples o f oxyalkylenated nonionic surfactants that may be mentioned include :
  • esters of saturated or unsaturated and linear or branched C 8 - C30 acids and of polyethylene glycols are esters of saturated or unsaturated and linear or branched C 8 - C30 acids and of polyethylene glycols;
  • the surfactants contain a number o f mo les o f 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 C8-C30 alcohols comprising from 1 to 100 mol of ethylene oxide; and polyoxyethylenated esters of saturated or unsaturated and linear or branched C8-C30 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 nonionic surfactants monoglycerolated or polyglycerolated C8-C40 alcohols are preferably used.
  • the monoglycerolated or polyglycerolated C8-C40 alcohols correspond to the formula (A7) below:
  • R 2 9 represents a linear or branched C8-C40 and preferably C 8 - C30 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 comprising 1.5 mol of glycerol, oleyl alcohol comprising 4 mol of glycerol (INCI name: Polyglyceryl-4 Oleyl Ether), oleyl alcohol comprising 2 mol of glycerol (INCI name: Polyglyceryl-2 Oleyl Ether), cetearyl alcohol comprising 2 mol of glycerol, cetearyl alcohol comprising 6 mol of glycerol, oleocetyl alcohol comprising 6 mol of glycerol, and octadecanol comprising 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.
  • Use is more preferably made, among the mono- or polyglycerolated alcohols, of the Cs/Cio alcohol comprising 1 mol of glycerol, the C 10 /C 12 alcohol comprising 1 mol of glycerol and the C 12 alcohol comprising 1.5 mol of glycerol.
  • the surfactant used in the composition o f the invention is chosen from nonionic monooxyalkylenated or polyoxyalkylenated and monoglycerolated or polyglycero lated surfactants, more particularly monooxyethylenated or polyoxyethylenated, or monooxypropylenated or po lyoxypropylenated, nonionic surfactants, or a combination thereo f, more particularly monooxyethylenated or polyoxyethylenated.
  • the surfactant(s) are chosen from nonionic surfactants or from anionic surfactants . More particularly, the surfactant(s) present in the composition are chosen from nonionic surfactants .
  • the nonionic surfactants are chosen from polyoxyethylenated sorbito l esters and polyoxyethylenated fatty alcoho ls, 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 according to the invention comprises one or more basifying agents .
  • the basifying agent(s) may be mineral or organic or hybrid.
  • the term "mineral compound” means any compound bearing in its structure one or more elements from co lumns 1 to 13 of the Periodic Table o f the Elements other than hydrogen.
  • the mineral basifying agent contains one or more elements from columns 1 and 2 of the Perio dic Table of the Elements other than hydrogen.
  • the mineral basifying agent has the fo llowing structure :
  • Z 2 denotes a metal from columns 1 to 13 and preferably 1 or 2 of the Periodic Table of the Elements, such as sodium or potassium;
  • Zi x denotes an anion chosen from the ions C0 3 2 , OH “ , HC0 3 2” , Si0 3 2” , HP0 4 2” , P0 4 3” and B 4 0 7 2" , and preferably from the ions C0 3 2 , OH " and Si0 3 2" ;
  • x denotes 1, 2 or 3;
  • y denotes 1, 2, 3 or 4;
  • n and n denote, independently of each other, 1, 2, 3 or 4;
  • the mineral basifying agent(s) are preferably chosen from aqueous ammonia, alkali carbonates or bicarbonates such as sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium hydroxide (soda), potassium hydroxide (potash), sodium metasilicate and potassium metasilicate, and a mixture thereof.
  • the basifying agent is a mineral base chosen from alkali metal carbonates.
  • 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 functional group 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 (III) below: Rx Rz
  • W is a divalent Ci-C 6 alkylene residue optionally substituted with a hydroxyl group or a Ci-C 6 alkyl radical; and/or optionally interrupted with one or more heteroatoms such as O, or NRu; Rx, Ry, Rz, Rt and Ru, which may be identical or different, represent a hydrogen atom or a Ci-C 6 alkyl, Ci-C 6 hydroxyalkyl or Ci- C 6 aminoalkyl radical.
  • Examples of amines of formula (II) that may be mentioned 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 Ci-Cs alkyl groups bearing one or more hydroxyl radicals.
  • Organic amines chosen from alkanolamines, such as mono-, di- or trialkanolamines, comprising from one to three identical or different C 1 -C4 hydroxyalkyl radicals, are suitable in particular for the implementation of the invention.
  • MAA monoethanolamine
  • diethanolamine triethanolamine
  • monoisopropanolamine diisopropanolamine
  • N,N- dimethylethanolamine 2-amino-2-methyl- 1 -propanol
  • triisopropanolamine 2 -amino -2 -methyl- 1 ,3 -propanediol
  • 2- propanediol 3-dimethylamino- 1 ,2-propanediol
  • tris(hydroxymethyl)amino methane tris(hydroxymethyl)amino methane.
  • amino acids which can be used are of natural or synthetic origin, in their L, D or racemic form, and comprise at least one acid functional group chosen more particularly from carboxylic acid, sulfonic acid, phosphonic acid or phosphoric acid functional groups.
  • the amino acids can be in the neutral or ionic form.
  • amino acids which can be used in the present invention, of aspartic acid, glutamic acid, alanine, arginine, ornithine, citrulline, asparagine, carnitine, cysteine, glutamine, glycine, histidine, lysine, iso leucine, leucine, methionine, N-phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine and valine.
  • amino acids which can be used in the present invention, of aspartic acid, glutamic acid, alanine, arginine, ornithine, citrulline, asparagine, carnitine, cysteine, glutamine, glycine, histidine, lysine, iso leucine, leucine, methionine, N-phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine and valine.
  • the amino acids are basic amino acids comprising an additional amine functional group optionally included in a ring or in a ureido functional group .
  • Such basic amino acids are preferably chosen from those corresponding to formula (IV) below :
  • R represents a group chosen from:
  • the compounds corresponding to formula (IV) are histidine, lysine, arginine, ornithine and citrulline.
  • the organic amine may also be chosen from organic amines o f heterocyclic type. Besides histidine that has already been mentioned in the amino acids, mention may in particular be made o f pyridine, piperidine, imidazole, triazo le, 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 o f carnosine, anserine and balenine.
  • the organic amine may also be chosen from compounds comprising a guanidine function.
  • amines o f this type that can be used in the present invention, besides arginine, which has already been mentioned as an amino acid, mention may be made especially o f 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 o f 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 (IV), and compounds comprising a guanidine function, and mixtures thereof.
  • the basifying agent(s) are chosen from alkano lamines such as monoethanolamine (MEA) .
  • the composition according to the invention has a content of organic 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 said composition.
  • the composition according to the invention or else the process according to the invention does not use aqueous ammonia, or a salt thereo f, as basifying agent.
  • composition or the process according to the invention does use aqueous ammonia, or a salt thereo f, as basifying agent, its content should not exceed 0.03 %> by weight (expressed as NH 3 ) and preferably should not exceed 0.01 % by weight, relative to the weight of the composition of the invention.
  • the amount of basifying agent(s) other than the aqueous ammonia is greater than that of the aqueous ammonia (expressed as NH 3 ) .
  • composition according to the invention comprises one or more oxidation bases .
  • the oxidation bases may be chosen from heterocyclic bases and benzenic bases, and mixtures thereof.
  • the oxidation bases are chosen from para- phenylene diamines, bis (phenyl) alky lene diamines, para-aminophenols, ortho-aminopheno ls and heterocyclic bases, and the addition salts thereo f.
  • para-phenylenediamines examples that may be mentioned include para-phenylenediamine, para-tolylenediamine, 2- chloro-para-phenylenediamine, 2, 3 -dimethyl-para-pheny lene diamine, 2, 6 -dimethyl-para-pheny lene diamine, 2,6-diethyl-para- phenylenediamine, 2,5 -dimethyl-para-phenylenediamine, N,N- dimethyl-para-phenylenediamine, ⁇ , ⁇ -diethyl-para-pheny lene diamine, ⁇ , ⁇ -dipropyl-para-pheny lene diamine, 4 -amino -N,N- diethyl- 3 - methylaniline, N,N-bis(P -hydroxy ethyl) -para-phenylenediamine, 4- N,N-bis( -hydroxy ethyl) amino -2 -met hylaniline,
  • para-phenylenediamine para-tolylenediamine, 2-isopropyl-para- phenylenediamine, 2- -hydroxyethyl-para-phenylenediamine, 2- ⁇ - hydroxyethyloxy-para-phenylenediamine, 2, 6 -dimethyl-par a- phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2, 3 -dimethyl- par a-phenylenediamine, N, N-bis( - hydroxy ethyl) -par a- phenylenediamine, 2-chloro-para-phenylenediamine and 2- ⁇ - acetylaminoethyloxy-para-phenylenediamine, and the addition salts thereo f with an acid, are particularly preferred.
  • bis(phenyl)alkylenediamines examples that may be mentioned include N,N'-bis( -hydroxyethyl)-N,N'-bis(4'- aminophenyl)- l ,3 -diaminopropanol, N, N'-bis( -hydroxy ethyl)-N, N'- bis(4'-aminophenyl)ethylenediamine, N,N'-bis(4- aminophenyl)tetramethylenediamine, N, N'-bis( -hydroxy ethyl) -N,N '- bis(4- amino phenyl)tetramethylenediamine, N,N'-bis(4- methylaminophenyl)tetramethylenediamine, N,N'-bis(ethyl)-N,N'- bis(4'-amino-3 '-methylphenyl)ethylenediamine and l , 8-bis(2,5 - dia
  • para-aminophenols examples that may be mentioned include para-aminophenol, 4-amino-3 -methylpheno l, 4- amino-3 -fluoropheno l, 4-amino-3 -chlorophenol, 4-amino-3 - hydroxymethylpheno l, 4-amino-2-methylpheno l, 4-amino-2- hydroxymethylpheno l, 4-amino-2-methoxymethylpheno l, 4-amino-2- amino methylpheno l, 4-amino-2-( -hydroxyethylaminomethyl)pheno l and 4-amino-2-fluorophenol, and the addition salts thereof with an acid.
  • heterocyclic bases by way o f example, o f pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
  • pyridine derivatives that may be mentioned are the compounds described, for examp le, 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.
  • Other pyridine oxidation bases that are useful in the present invention are the 3-aminopyrazolo[ 1 ,5-a]pyridine oxidation bases or the addition salts thereof described, for example, in patent application FR 2 801 308.
  • Examples that may be mentioned include pyrazolo[ 1 ,5- a]pyrid-3-ylamine, 2-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
  • pyrimidine derivatives that may be mentioned are the compounds described, for example, in patents DE 2359399, JP 88- 169571, JP 05-63124 and EP 0 770 375 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 addition salts thereof, and tautomeric forms thereof, when a tautomeric equilibrium exists.
  • pyrazole derivatives that may be mentioned are the compounds described in patents DE 3843892 and DE 4133957 and patent applications WO 94/08969, WO 94/08970, FR-A-2733 749 and DE 19543988, 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-d
  • Use will preferably be made of a 4,5-diaminopyrazole and even more preferentially of 4,5-diamino- 1 -( -hydroxyethyl)pyrazole and/or a salt thereof.
  • pyrazole derivatives of diamino-N,N-dihydropyrazolopyrazolones and in particular those described in application FR-A-2886 136, such as the following compounds and the addition salts thereof: 2,3-diamino-6,7-dihydro- lH,5H-pyrazolo[ 1 ,2-a]pyrazol- 1 -one, 2-amino-3-ethylamino-6,7- dihydro- lH,5H-pyrazolo[ 1 ,2-a]pyrazol- 1 - one, 2-amino-3- isopropylamino-6,7-dihydro-lH,5H-pyrazolo[ 1 ,2-a]pyrazol- 1 -one, 2- amino-3-(pyrrolidin-l-yl)-6,7-dihydro-lH,5H-pyrazolo[ 1 ,2-a]pyrazol- 1-one,
  • heterocyclic bases use will preferably be made of 4,5- diamino- 1 - ( ⁇ -hydro xyethyl)pyrazole and/or 2,3-diamino-6,7-dihydro- lH,5H-pyrazolo[l,2-a]pyrazol-l-one and/or a salt thereof.
  • composition according to the invention also comprises one or more couplers chosen from the couplers of formula (I) below and the addition salts thereof, isomers thereof, tautomers thereof, solvates thereof and dimers thereof:
  • s denotes 0 or 1
  • p denotes 0 or 1
  • Ri, R 2 , R 3 , R 4 , R 5 , R 6 , R7 and Rs denote, independently of each other, a hydrogen atom; an amino group; a halogen atom; a hydroxyl group; a Ci-Cs alkoxy group; a C 2 -C 5 acylamino group; a group CHO, a linear, branched or cyclic Ci-Cis alkyl or C 2 -Cis alkylene group, one or more carbon atoms possibly being replaced with one or more heteroatoms such as oxygen, sulfur or nitrogen, an aryl group, the alkyl, alkylene or aryl groups possibly being substituted with one or more groups chosen from hydroxyl, nitro, nitrile, cyano, carboxylic acid, Ci-Cis alkyl ester, carbamate, carboxamide, amino, alkylamino, dialkylamino, carboxyl, alkoxy and halogen atoms, C 3 -C 6 cycloal
  • the groups R 7 and Rs may form, with the atom that bears them, a ring optionally comprising one or more heteroatoms, this ring possibly being substituted with a C i -C 6 alkyl group or a hydroxyl group, or possibly being fused with one or more other rings optionally bearing one or more heteroatoms, one or more carbon atoms o f the ring(s) possibly being replaced with one or more carbonyl groups .
  • R 7 may also denote a radical derived from a perimidinyl group of formula (I), thus leading to a dimer; the two perimidinyl groups are then preferably linked via the carbon atoms in position 2,
  • R 7 may denote a linear or branched C 1 - C 1 0 alkylene chain, one or more carbon atoms possibly being replaced with one or more heteroatoms such as oxygen, sulfur or nitrogen and/or optionally comprising a ring, or alternatively a saturated or unsaturated ring, optionally comprising one or more heteroatoms; a chain comprising several and preferably two saturated or unsaturated rings linked together via a covalent bond or via a heteroatom, the chains or the ring possibly being substituted with a hydroxyl group or with a perimidinyl radical o f formula (I) preferably via the carbon atom in position 2,
  • R 4 when R 4 is in position 7 and R 5 is in position 6, then they can form, together with the carbon atoms that bear them, a 5 - to 8- membered ring optionally comprising one or more heteroatoms .
  • couplers o f formula (I) are chosen from the fo llowing compounds :
  • p denotes 1 .
  • p denotes 0.
  • R3 and R 6 represent a hydrogen atom.
  • At least one of the groups Ri and R 2 represent a hydrogen atom.
  • R 4 and R 5 represent a hydrogen atom.
  • composition o f the invention may also comprise one or more additional couplers other than the couplers that are usually used, of formula (I) as described previously.
  • couplers mention may be made especially o f meta-phenylenediamines, meta-aminopheno ls, meta-dipheno ls, naphthalene-based couplers and heterocyclic couplers, and also the addition salts thereof.
  • Examples that may be mentioned include 1,3- dihydroxybenzene, 1 ,3-dihydroxy-2-methylbenzene, 4-chloro- 1 ,3- dihydroxybenzene, 2,4-diamino- 1 -(P-hydroxyethyloxy)benzene, 2- amino -4 -( ⁇ - hydroxy ethy lamino) - 1 -methoxybenzene, 1,3- diaminobenzene, 1 ,3-bis(2,4-diaminophenoxy)propane, 3- ureidoaniline, 3-ureido- 1 -dimethylaminobenzene, sesamol, 1- ⁇ - hydroxyethylamino-3,4-methylenedioxybenzene, a-naphthol, 2- methyl- 1 -naphthol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N- methylindole, 2-amino-3-hydroxypyridine, 6- hydroxy
  • addition salts of the oxidation bases and couplers that can be used within the context of the invention are especially chosen from the addition salts with an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
  • an acid such as the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
  • the oxidation base(s) each advantageously represent from
  • composition 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 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.
  • composition according to the invention may optionally comprise one or more synthetic or natural direct dyes, chosen from ionic or nonionic species, preferably cationic or nonionic species .
  • Examples o f suitable synthetic direct dyes include azo direct dyes; (poly)methine dyes such as cyanins, hemicyanins and styryls; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; and phthalocyanin dyes, alone or as mixtures.
  • azo direct dyes include azo direct dyes; (poly)methine dyes such as cyanins, hemicyanins and styryls; carbonyl dyes; azine dyes; nitro(hetero)aryl dyes; tri(hetero)arylmethane dyes; porphyrin dyes; and phthalocyanin dyes, alone or as mixtures.
  • Use may also be made of extracts or decoctions comprising these natural dyes and in particular henna-based poultices or extracts .
  • the direct dye(s) more particularly represent from 0.00 1 % to 10% by weight and preferably from 0.005 % to 5 % by weight of the total weight of the composition.
  • composition according to the invention may be an anhydrous or aqueous composition. It is preferably aqueous.
  • aqueous composition is understood to mean a composition comprising more than 5 % by weight o f water, preferably more than 10% by weight of water and more advantageously still more than 20% by weight of water.
  • the cosmetic composition according to the invention may optionally comprise one or more organic solvents.
  • Examples o f organic so lvents that may be mentioned include linear or branched C 2 - C 4 alkano ls, such as ethanol and isopropano l; glycero l; polyo ls and polyo l ethers, for instance 2-butoxyethano l, propylene glyco l, dipropylene glyco l, propylene glyco l monomethyl ether, diethylene glyco l monomethyl ether and monoethyl ether, and also aromatic alcoho ls, for instance benzyl alcohol or phenoxyethano l, and mixtures thereof.
  • the organic so lvent(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.
  • 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 thereo f; mineral thickeners, and in particular fillers such as clays or talc; organic thickeners with, in particular, anionic, cationic, nonionic and amphoteric polymeric associative thickeners other than the polymers mentioned previously; 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 thereo f; mineral thickeners, and in particular fillers such as clays or talc; organic thickeners with, in particular, anionic, cationic, nonionic and amphoteric polymeric associative thickeners other
  • the above adjuvants are generally present in an amount for each o f them o f between 0.01 % and 20% by weight relative to the weight of the composition.
  • the composition may also comprise one or more mineral or organic thickeners .
  • the mineral thickeners may be chosen from organophilic clays and mineral fillers .
  • the organophilic clay may be chosen from montmoriUonite, bentonite, hectorite, attapulgite and sepiolite, and mixtures thereof.
  • the clay is preferably a bentonite or a hectorite .
  • These clays can be modified with a chemical compound chosen from quaternary ammoniums, tertiary amines, amine acetates, imidazo lines, amine soaps, fatty sulfates, alkylarylsulfonates and amine oxides, and mixtures thereof.
  • Organophilic clays that may be mentioned include quaternium- 1 8 bentonites, such as those so ld under the names Bentone 3 , Bentone
  • the mineral thickeners are chosen from inorganic fillers, in particular kao linite.
  • the organic thickeners may be chosen from associative or non- associative thickening polymers, in particular associative thickening polymers.
  • the term "associative thickening polymer” means a thickening polymer comprising at least one C 8 - C 30 fatty chain and at least one hydrophilic unit.
  • the associative thickening polymers are chosen from polyurethane polyethers comprising in their chain both hydrophilic blo cks usually o f po lyoxyethylenated nature and hydrophobic blo cks, which may be aliphatic sequences alone and/or cycloaliphatic and/or aromatic sequences,
  • Aculyn 46® is a po lycondensate of polyethylene glyco l containing 150 or 1 80 mo l o f ethylene oxide, of stearyl alcoho l and o f methylenebis(4-cyclohexyl isocyanate) (SMDI), at 15 % by weight in a matrix o f maltodextrin (4%) and water (8 1 %);
  • Aculyn 44® is a polycondensate of polyethylene glyco l containing 150 or 1 80 mo l o f ethylene oxide, o f decyl alcoho l and of methylenebis(4-cyclohexyl isocyanate) (SMDI), at 35 % by weight in a mixture of propylene glyco l (39%) and water (26%)] .
  • the thickeners represent from 1 % to 30% by weight relative to the weight of the composition.
  • composition according to the invention may comprise one or more chemical oxidizing agents .
  • the chemical oxidizing agent(s) are chosen from hydrogen peroxide, urea peroxide, alkali metal bromates or ferricyanides, peroxygenated salts, for instance persulfates, perborates, peracids and precursors thereof, and percarbonates o f alkali metals or alkaline-earth metals, and peracids and precursors thereo f.
  • One or more redox enzymes such as laccases, peroxidases and 2-electron oxidoreductases (such as uricase), optionally in the presence o f the respective donor or cofactor thereof, may also be used as oxidizing agent.
  • This oxidizing agent advantageously consists o f hydrogen peroxide, in particular in aqueous solution (aqueous hydrogen peroxide so lution), the concentration of which may vary, 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 composition.
  • composition used in the process according to the invention corresponds to the composition as defined previously and that is free of chemical oxidizing agent; this composition also being used in the presence of at least one chemical oxidizing agent.
  • the process according to the invention consists in applying to the said fibres a composition according to the invention, in the presence of at least one chemical oxidizing agent.
  • composition used in the process according to the invention i. e. used in the presence o f at least one chemical oxidizing agent
  • the temperature during the dyeing process is conventionally between room temperature (between 15 °C and 25 ° C) and 80°C and preferably between room temperature and 60°C .
  • the human keratinous fibres are advantageously rinsed with water. They can optionally be washed with a shampoo, fo llowed by rinsing with water, before being dried or left to dry.
  • composition applied in the process according to the invention i. e. used in the presence o f at least one chemical o xidizing agent
  • compositions preferably two or three compositions .
  • the composition applied in the process according to the invention results from the mixing o f two compositions.
  • composition (A) comprising at least one oxidation base, at least one coupler chosen from the couplers o f formula (I) and at least one basifying agent is mixed with a composition (B) comprising at least one chemical oxidizing agent; at least one of the compositions (A) and (B) comprising at least one fatty substance, and at least one of the compositions (A) and (B) comprising at least one surfactant, the fatty substance content o f the composition according to the invention, resulting from the mixing o f compositions (A) and (B), comprising at least 25 % by weight of fatty substance.
  • At least one of the compositions (A) and (B) is advantageously aqueous.
  • composition (A) is aqueous.
  • composition (B) is also aqueous .
  • composition (A) preferably comprises at least 50% by weight of fatty substances, and more preferably still at least 50% by weight of fatty substances that are liquid at room temperature (25 °C), relative to the weight of this composition (A) .
  • composition (A) is a direct emulsion (oil-in-water:
  • 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 used in the process according to the invention results from the mixing of three compositions.
  • the three compositions are aqueous or alternatively at least one of them is anhydrous.
  • anhydrous cosmetic composition is understood to mean a cosmetic composition exhibiting a water content of less than 5% by weight, preferably of less than 2% by weight and more preferably still of less than 1% by weight, relative to the weight of the said composition.
  • water present in the composition is more particularly "bound water”, such as water of crystallization in salts, or traces of water absorbed by the raw materials used in the preparation of the compositions according to the invention.
  • ⁇ ' aqueous compositions
  • ⁇ ' anhydrous composition
  • the anhydrous composition ( ⁇ ') then preferably comprises at least one fatty substance, and more preferentially at least one liquid fatty substance.
  • Composition ( ⁇ ') then preferably comprises at least one oxidation base and at least one coupler chosen from the couplers of formula (I).
  • Composition (C) then preferably comprises at least one chemical oxidizing agent.
  • the basifying agent(s) are included in compositions ( ⁇ ') and/or ( ⁇ ') and preferably only in composition ( ⁇ ').
  • the surfactant(s) they are included in at least one of compositions ( ⁇ '), ( ⁇ ') and (C).
  • the composition according to the invention i.e. the composition derived from the mixing of the three compositions ( ⁇ '), ( ⁇ ') and (C), has a fatty substance content of at least 25% by weight relative to the weight of the composition derived from the mixing of the abovementioned three compositions.
  • 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 a second compartment containing composition (B) as described above; the compositions (A) and (B) of the compartments being intended to be mixed together before application to give a composition according to the invention; the amount of fatty substance of which represents at least 25% by weight relative to the weight of the formulation resulting from the mixing of compositions (A) and (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 cosmetic composition ( ⁇ ') as described above and at least 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 composition according to the invention; the amount of fatty substance in the composition representing at least 25% by weight relative to the weight of the composition of the invention, i.e. resulting from the mixing of compositions ( ⁇ '), ( ⁇ ') and (C).
  • compositions are prepared in which the amounts are expressed in grams of materials in their given state.
  • Vitamin C L-ascorbic acid 0.25
  • composition A -10 parts of composition A
  • Each of the mixtures is then applied to locks of natural hair containing 90% white hairs.
  • the “mixture/lock” bath ratio is respectively 10/1 (g/g).

Abstract

La présente invention se rapporte à une composition cosmétique de traitement des fibres kératiniques, en particulier des fibres kératiniques humaines telles que les cheveux, contenant au moins 25% en poids, par rapport au poids total de la composition, d'un ou de plusieurs corps gras, un ou plusieurs tensioactifs, un ou plusieurs agents alcalinisants, une ou plusieurs bases d'oxydation, et un ou plusieurs coupleurs représentés par la formule (I) ci-dessous, leurs sels d'addition, leurs isomères, leurs tautomères, leurs solvates et leurs dimères : (I). L'invention concerne également des procédés d'utilisation de la composition de l'invention ainsi qu'un dispositif à plusieurs compartiments.
PCT/EP2012/075094 2011-12-13 2012-12-11 Composition de coloration d'oxydation comprenant un coupleur particulier dans un milieu riche en corps gras, ainsi que procédés et dispositif adapté à ceux-ci WO2013087631A2 (fr)

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FR1161571A FR2983714A1 (fr) 2011-12-13 2011-12-13 Composition de coloration d'oxydation comprenant un coupleur particulier dans un milieu riche en corps gras, procedes et dispositif approprie
FR1161571 2011-12-13
US201261585007P 2012-01-10 2012-01-10
US61/585,007 2012-01-10

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CN104418811A (zh) * 2013-08-20 2015-03-18 江南大学 一类2,3-二氢萘嵌间二氮杂苯类似物、其合成方法、药物组合物及用途
US9193869B2 (en) 2013-08-26 2015-11-24 Xerox Corporation Dye compounds, method of making the compounds and ink composition employing the compounds
CN104739836B (zh) * 2014-09-30 2017-03-29 三峡大学 一种小分子抑制剂及其应用
US9738811B2 (en) 2013-08-26 2017-08-22 Xerox Corporation Phase change inks containing wax-soluble near-infrared dyes
US20170314007A1 (en) * 2014-09-30 2017-11-02 China Three Gorges University Medicament design pocket of ornithine decarboxylase and application of medicament design pocket
CN113337096A (zh) * 2021-06-23 2021-09-03 西北师范大学 一种凹凸棒石-氧化石墨烯复合粉体及其制备方法和用途
CN114773220A (zh) * 2021-12-21 2022-07-22 西安阿伯塔资环分析测试技术有限公司 一种刚性双尾表面活性剂及其制备方法和清洁压裂液

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CN104418811A (zh) * 2013-08-20 2015-03-18 江南大学 一类2,3-二氢萘嵌间二氮杂苯类似物、其合成方法、药物组合物及用途
CN104418811B (zh) * 2013-08-20 2017-05-31 江南大学 一类2,3‑二氢萘嵌间二氮杂苯类似物、其合成方法、药物组合物及用途
US8884012B1 (en) * 2013-08-26 2014-11-11 Xerox Corporation Dye compound and method of making the compound
JP2015042639A (ja) * 2013-08-26 2015-03-05 ゼロックス コーポレイションXerox Corporation 染料化合物およびこの化合物を製造する方法
US9193869B2 (en) 2013-08-26 2015-11-24 Xerox Corporation Dye compounds, method of making the compounds and ink composition employing the compounds
US9738811B2 (en) 2013-08-26 2017-08-22 Xerox Corporation Phase change inks containing wax-soluble near-infrared dyes
DE102014216738B4 (de) * 2013-08-26 2021-04-01 Xerox Corporation Perimidinkoppler und verfahren zu dessen herstellung
CN104739836B (zh) * 2014-09-30 2017-03-29 三峡大学 一种小分子抑制剂及其应用
US20170314007A1 (en) * 2014-09-30 2017-11-02 China Three Gorges University Medicament design pocket of ornithine decarboxylase and application of medicament design pocket
CN113337096A (zh) * 2021-06-23 2021-09-03 西北师范大学 一种凹凸棒石-氧化石墨烯复合粉体及其制备方法和用途
CN114773220A (zh) * 2021-12-21 2022-07-22 西安阿伯塔资环分析测试技术有限公司 一种刚性双尾表面活性剂及其制备方法和清洁压裂液
CN114773220B (zh) * 2021-12-21 2024-01-26 西安阿伯塔资环分析测试技术有限公司 一种刚性双尾表面活性剂及其制备方法和清洁压裂液

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