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WO2010133575A2 - Composition de coloration comprenant une base d'oxydation para-phénylènediamine secondaire et une substance grasse avec du silicone ou une substance grasse liquide sans silicone - Google Patents

Composition de coloration comprenant une base d'oxydation para-phénylènediamine secondaire et une substance grasse avec du silicone ou une substance grasse liquide sans silicone Download PDF

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Publication number
WO2010133575A2
WO2010133575A2 PCT/EP2010/056784 EP2010056784W WO2010133575A2 WO 2010133575 A2 WO2010133575 A2 WO 2010133575A2 EP 2010056784 W EP2010056784 W EP 2010056784W WO 2010133575 A2 WO2010133575 A2 WO 2010133575A2
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Prior art keywords
composition
silicone
chosen
radical
silicones
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WO2010133575A3 (fr
Inventor
Jean-Baptiste Saunier
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LOreal SA
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LOreal SA
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Priority claimed from FR0953319A external-priority patent/FR2945730B1/fr
Priority claimed from FR0953322A external-priority patent/FR2945731B1/fr
Application filed by LOreal SA filed Critical LOreal SA
Publication of WO2010133575A2 publication Critical patent/WO2010133575A2/fr
Publication of WO2010133575A3 publication Critical patent/WO2010133575A3/fr
Anticipated expiration legal-status Critical
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • A61K2800/31—Anhydrous

Definitions

  • a subject-matter of the invention is a dyeing composition comprising at least one specific secondary para-phenylenediamine oxidation base and at least one fatty substance chosen from a) non-silicone liquid fatty substances and b) silicones.
  • Another subject- matter of the invention is the use of this composition for dyeing keratinous fibres and the dyeing method employing this composition.
  • a subject-matter of the invention is a multicompartment device.
  • oxidation bases such as ortho- or para- phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds.
  • oxidation bases are colourless or weakly coloured compounds which, in combination with oxidizing products, can give rise, by an oxidative coupling process, to coloured compounds.
  • couplers or colouring modifiers the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds, such as indole compounds.
  • the "permanent" colouring obtained by virtue of these oxidation dyes furthermore has to satisfy a certain number of requirements.
  • it must be without disadvantage toxicologically, it must make it possible to obtain shades within the desired intensity and it must behave well in the face of external agents, such as light, bad weather, washing, permanent waving, perspiration and rubbing.
  • the dyes must also make it possible to cover white hair and, finally, be as non-selective as possible, that is to say make it possible to obtain the smallest possible differences in colouring along the same keratinous fibre, which is generally differently sensitized (i.e. damaged) between its tip and its root.
  • oils in the field of oxidation hair dyeing (see, for example, FR 2 464 710, WO2008/020730 or US 7 458 995) . It is also known to use compositions employing silicones. For example, aminated, polyoxyalkylenated silicones, or silicone gums/resins, have been used in combination with cationic direct dyes (EP 1 049 447) . Other specific aminated silicones have been used in combination with oxidation dyes (EP 1 312 343) . However, the colourings obtained with conventional oxidation dyes in combinations with these oils or with these silicones are not satisfactory, in particular in terms of chromaticity, of power, of selectivity and/or of resistance to external agents.
  • the aim of the present invention is to obtain a composition for dyeing the hair which exhibits improved dyeing properties in terms of intensity or of chromaticity, and/or of selectivity and/or of resistance to external agents.
  • This aim is achieved with the present invention, a subject-matter of which is a composition for dyeing keratinous fibres comprising, in an appropriate dyeing medium: one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid:
  • fatty substances chosen from a) non- silicone liquids and b) silicones.
  • Another subject-matter of the invention is a dyeing method employing this composition.
  • Another subject-matter of the invention is the use of the composition of the present invention for dyeing keratinous fibres, in particular human keratinous fibres, such as the hair.
  • Another subject-matter of the invention is a multicompartment device comprising, in one of the compartments, the dyeing composition according to the invention and, in another compartment, a composition comprising one or more oxidizing agents.
  • the device comprises a first compartment including one or more oxidation bases chosen from the compound of formula (I) or its salts with an acid and optionally one or more oxidation bases other than the compound of formula (I) or its salts and optionally one or more couplers, a second compartment including a composition comprising one or more fatty substances chosen from a) non-silicone liquids and b) silicones, and a third compartment including a composition comprising one or more oxidizing agents.
  • composition of the present invention makes it possible in particular to obtain a composition for dyeing keratinous fibres which is suitable for use in oxidation dyeing and which makes it possible to obtain a colouring with varied, intense or chromatic, attractive and not very selective shades which are highly resistant to the various attacks which hair may be subjected to, such as shampoos, sweat, permanent deformations and light. It should be noted that, in that which will follow and unless otherwise indicated, the limits of a range of values are included within this range.
  • the compound of formula (I) can be in the form of cosmetically acceptable addition salts chosen in particular from the addition salts with an acid, such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulphonates, phosphates and acetates.
  • an acid such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulphonates, phosphates and acetates.
  • the compound of formula (I) or its salts are generally each present in an amount of between 0.001 and 10% by weight approximately of the total weight of the dyeing composition, preferably between 0.005 and 6%.
  • compositions comprise a) one or more non-silicone liquid fatty substances.
  • liquid fatty substance is understood to mean an organic compound which is liquid at ambient temperature (25°C) and at atmospheric pressure (760 mm of mercury) , which is insoluble in water under these conditions, that is to say with a solubility of less than 5% by weight, preferably of less than 1% by weight and more preferably still of less than 0.1% by weight in water, and which exhibits, in its structure, at least one hydrocarbon chain comprising at least 6 carbon atoms
  • non-silicone liquid fatty substance is understood to mean a liquid fatty substance as defined above not comprising a silicon atom in its structure.
  • non-silicone liquid fatty substances are generally soluble in organic solvents under the same temperature and pressure conditions, such as, for example, chloroform, ethanol, benzene, liquid paraffin or decamethylcyclopentasiloxane .
  • non-silicone liquid fatty substances according to the invention are chosen in particular from liquid lower C6-C16 alkanes, non-silicone oils of animal, vegetable, mineral or synthetic origin, liquid fatty alcohols, liquid fatty acids or liquid fatty alcohol and/or fatty acid esters.
  • fatty alcohols, esters and acids exhibit more particularly at least one saturated or unsaturated and linear or branched hydrocarbon group comprising from 6 to 30 carbon atoms which is optionally substituted, in particular by one or more hydroxyl groups (in particular from 1 to 4 hydroxyl groups) . If they are unsaturated, these compounds can comprise from one to three conjugated or nonconjugated carbon-carbon double bonds.
  • the lower C ⁇ -Ci ⁇ alkanes are linear or branched or optionally cyclic.
  • the alkanes can be chosen from hexane, dodecane or isoparaffins, such as isohexadecane and isodecane .
  • non-silicone oils of animal, vegetable, mineral or synthetic origin which can be used in the composition of the invention, for example, of: hydrocarbon oils of animal origin, such as perhydrosqualene;
  • triglyceride oils of vegetable or synthetic origin such as liquid triglycerides of fatty acids comprising from 6 to 30 carbon atoms, such as triglycerides of heptanoic acid or octanoic acid or also, for example, sunflower oil, maize oil, soybean oil, cucumber oil, grape seed oil, sesame oil, hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocado oil, camellia seed oil, olive oil, peach kernel oil, mango seed oil, argan oil, quinoa seed oil, wheat germ oil, pomegranate seed oil, camelina seed oil, blackcurrant seed oil, jojoba seed oil, coconut oil, triglycerides of caprylic/capric acids, such as those sold by Stearineries Dubois or those sold under the names Miglyol® 810, 812 and 818 by Dynamit Nobel, jojoba oil or shea butter oil; linear or branched hydrocarbons of
  • - fluorinated oils such as perfluoromethylcyclopentane and perfluoro-1, 3-dimethylcyclohexane, sold under the names "Flutec® PCl” and “Flutec® PC3" by BNFL Fluorochemicals; perfluoro-1, 2-dimethylcyclobutane; perfluoroalkanes, such as dodecafluoropentane and tetradecafluorohexane, sold under the names of "PF 5050®” and "PF 5060®” by 3M, or also bromoperfluorooctyl, sold under the name "Foralkyl®” by Atochem; nonafluoromethoxybutane and nonafluoroethoxyisobutane; or perfluoromorpholine derivatives, such as 4- (trifluoromethyl) perfluoromorpholine, sold under the name "PF 5052®” by 3M.
  • perfluoromorpholine derivatives such as 4- (
  • the non-silicone oils of animal, vegetable, mineral or synthetic origin which can be used in the composition of the invention are chosen from oils of mineral origin, such as petrolatum or polydecenes, or oils of vegetable origin, such as camellia seed oil, olive oil, peach kernel oil, apricot kernel oil, avocado oil, mango seed oil, argan oil, quinoa seed oil, wheat germ oil, sunflower seed oil, grape seed oil, pomegranate seed oil, camelina seed oil, blackcurrant seed oil, jojoba seed oil and coconut oil .
  • the liquid fatty alcohols which can be used in the composition according to the invention are unsaturated and/or branched and comprise from 6 to 30 carbon atoms and more particularly from 8 to 30 carbon atoms.
  • the liquid fatty acids which can be used in the composition according to the invention can be unsaturated and/or branched carboxylic acids and they comprise from 6 to 30 carbon atoms, in particular from 9 to 30 carbon atoms. They are more particularly chosen from oleic acid, linoleic acid, isostearic acid and their mixtures.
  • liquid fatty alcohol and/or fatty acid esters advantageously different from the triglycerides mentioned above, which can be used in the composition according to the invention, they can result from C3-C30 carboxylic acid and from C1-C30 alcohol, at least one of the acid or of the alcohol being branched and/or unsaturated and at least one of the acid or of the alcohol comprising more than 6 carbon atoms.
  • Use may also be made of esters of C4-C22 di- or tricarboxylic acids and of C1-C22 alcohols and esters of mono-, di- or tricarboxylic acids and of di-, tri-, tetra- or pentahydroxy alcohols comprising from 2 to 26 carbon atoms .
  • Mention may in particular be made of diisopropyl sebacate, diisopropyl adipate, diisostearyl adipate, octyldodecylstearoyl stearate, pentaerythrityl tetraisononanoate, pentaerythrityl tetraisostearate, triisostearyl citrate or trioctyldodecyl citrate.
  • the acid and the alcohol of the ester are saturated.
  • esters Preference is given, among the abovementioned esters, to the use of isopropyl palmitate, 2-ethylhexyl palmitate, 2-octyldecyl palmitate, myristates of branched alkyls, such as isopropyl myristate, t-butyl myristate or 2-octyldodecyl myristate, hexyl isostearate, butyl isostearate, isobutyl stearate, 2-hexyldecyl laurate and isononyl isononanoate .
  • branched alkyls such as isopropyl myristate, t-butyl myristate or 2-octyldodecyl myristate
  • hexyl isostearate butyl isostearate
  • isobutyl stearate 2-hexyldecyl laurate and isonon
  • esters of C7-C30 aromatic acid and of C1-C30 alcohol preferably esters of C 7 -Ci 7 aromatic acid and of C1-C20 alcohol.
  • esters are in particular C12-C15 alkyl benzoates, isostearyl benzoate, octyldodecyl benzoate, behenyl benzoate or 2-ethylhexyl benzoate.
  • liquid fatty substance or substances present in the composition according to the invention are chosen from linear or branched C ⁇ -Ci ⁇ alkanes, hydrocarbons of more than 16 carbon atoms, liquid triglycerides of fatty acids comprising from 6 to 30 carbon atoms, liquid fatty acids or liquid fatty alcohol and/or acid esters other than the triglycerides .
  • liquid fatty substance or substances according to the invention are chosen from linear or branched hydrocarbons of more than 16 carbon atoms and of mineral or synthetic origin, such as liquid petrolatum or polydecenes, oils of vegetable origin, liquid fatty acids, liquid fatty alcohol and/or fatty acid esters or their mixtures.
  • liquid fatty substance or substances are generally each present in an amount of between 0.01 and
  • compositions comprise b) one or more silicones .
  • sicone is understood to mean, in conformity with what is generally accepted, any organosilicon polymer or oligomer with a linear or cyclic and branched or crosslinked structure of variable molecular weight obtained by polymerization and/or by polycondensation of suitably functionalized silanes and essentially composed of a repetition of main units in which the silicon atoms are connected to one another via oxygen atoms (siloxane -Si-O-Si- bond), optionally substituted hydrocarbon radicals being directly connected via a carbon atom to the said silicon atoms (see, for example, the encyclopaedias Ullmann's Encyclopedia of Industrial Chemistry, Wiley- VCH Verlag GmbH & Co.
  • the commonest hydrocarbon radicals are linear or branched C1-C30 alkyl or alkenyl radicals, preferably alkyl and linear radicals, especially Ci-C 4 radicals and in particular a methyl radical, or aryl radicals and in particular a phenyl radical. These hydrocarbon radicals and in particular the alkyl radicals can be substituted by various groups.
  • organomodified silicones The silicones used in the composition according to the invention may be volatile or nonvolatile and soluble or insoluble in the composition. They can be provided in the form of oils, waxes, resins or gums.
  • the insoluble silicones are in particular dispersed in the compositions in the form of particles generally having a number-average size of between 2 nanometres and 100 micrometres, preferably between 20 nanometres and 20 micrometres (measured with a particle sizer) .
  • Organicpolysiloxanes are defined in more detail in the work by Walter Noll, Chemistry and Technology of Silicones, Academic Press (1968). They can be volatile or nonvolatile. When they are volatile, the silicones are chosen more particularly from those having a boiling point of between 60 0 C and 260 0 C and more particularly still from:
  • cyclic silicones comprising from 3 to 7 silicon atoms and preferably 4 or 5. They are, for example, octamethylcyclotetrasiloxane, sold in particular under the name of "Volatile Silicone
  • linear volatile silicones having from 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. They are, for example, decamethyltetrasiloxane, sold in particular under the name "SH 200" by Toray Silicone. Silicones coming within 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”.
  • nonvolatile silicone is understood to mean, within the meaning of the present invention, any silicone having a number of silicon atoms of greater than 7.
  • nonvolatile silicones of poly (di) alkylsiloxanes, poly (di) arylsiloxanes, poly (di) alkyl (di) arylsiloxanes, silicone gums and resins, polyorganosiloxanes modified by organofunctional groups, polysiloxane (A) - polyoxyalkylene (B) linear block copolymers of (A-B) n type with n > 3, grafted silicone polymers having a non-silicone organic backbone, composed of an organic main chain formed from organic monomers not comprising silicone, to which is grafted, inside the said chain and optionally at one at least of its ends, at least one polysiloxane macromonomer, grafted silicone polymers having a polysiloxane backbone grafted with non-silicone organic monomers, comprising a polysiloxane main chain to which is grafted, inside the said chain and optionally at one
  • the viscosity of the silicones is, for example, measured at 25°C according to Standard ASTM 445 Appendix C. Mention may be made, among these polyalkylsiloxanes, without implied limitation, of the following commercial products:
  • Mirasil oils sold by Rh ⁇ ne-Poulenc such as, for example, the oil 70 047 V 500 000; oils of the Mirasil series sold by Rhodia; oils of the 200 series from Dow Corning, such as, more particularly, DC200 with a viscosity of
  • the poly (di) alkyl (di) arylsiloxanes can in particular be chosen from linear and/or branched polydimethyl (methylphenyl) siloxanes or polydimethyl- diphenylsiloxanes with a viscosity of 1 x 10 ⁇ 5 to 5 x 10 "2 m 2 /s at 25°C.
  • Silbione oils of the 70 641 series from Rhodia oils of the Rhodorsil 70 633 and 763 series from Rhodia; the oil Dow Corning 556 Cosmetic Grade Fluid from Dow Corning; silicones of the PK series from Bayer, such as the product PK20; silicones of the PN and PH series from Bayer, such as the products PNlOOO and PHlOOO; - some oils of the SF series from General Electric, such as SF 1023, SF 1154, SF 1250 and SF 1265.
  • Silicone gums which can be used in accordance with the invention are in particular polydiorganosiloxanes having 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, tridecanes or their mixtures.
  • polydimethylsiloxane gums polydimethylsiloxane/methylvinylsiloxane gums, - polydimethylsiloxane/diphenylsiloxane gums, polydimethylsiloxane/phenylmethylsiloxane gums, polydimethylsiloxane/diphenylsiloxane/methylvinyl- siloxane gums.
  • silicones can also be employed, such as : a) mixtures formed from a polydimethylsiloxane gum hydroxylated at the chain end (named dimethiconol according to the nomenclature of the CTFA dictionary) and from a cyclic polydimethylsiloxane (named cyclomethicone according to the nomenclature of the CTFA dictionary) , such as the product Q2 1401 sold by Dow Corning; b) mixtures formed from a polydimethylsiloxane gum with a cyclic silicone, such as the product SF 1214 Silicone Fluid from General Electric; this product is a gum SF 30, corresponding to a dimethicone, having a number-average molecular weight of 500 000, dissolved in the oil SF 1202 Silicone Fluid, corresponding to decamethylcyclopentasiloxane; c) mixtures of two PDMSs with different viscosities and more particularly of a PDMS gum and of a PD
  • the product SF 1236 is the mixture of a gum SE 30 defined above, having a viscosity of
  • This product preferably comprises 15% of gum SE 30 and 85% of an oil SF 96.
  • the organopolysiloxane resins which can be used in accordance with the invention are crosslinked siloxane systems including the units: R2Si ⁇ 2 / 2, R3SiOi / 2, RSi ⁇ 3 / 2 and Si ⁇ 4 / 2, in which R represents a hydrocarbon group having from 1 to 16 carbon atoms or a phenyl group.
  • R denotes a lower Ci-C 4 alkyl radical, more particularly methyl, or a phenyl radical .
  • R denotes a lower Ci-C 4 alkyl radical, more particularly methyl, or a phenyl radical .
  • organomodified silicones which can be used in accordance with the invention are silicones as defined above which comprise, in their structure, one or more organofunctional groups attached via a hydrocarbon group.
  • organomodified silicones of the polyorganosiloxanes comprising: polyethyleneoxy and/or polypropyleneoxy groups optionally comprising C6-C24 alkyl groups, such as the products known as dimethicone copolyol, sold by Dow Corning under the name DC Fluid 190 or DC 1248, or the Silwet ® L 722, L 7500, L 77 and L 711 oils from Union Carbide, and (C12) alkyl methicone copolyol, sold by Dow Corning under the name Q2 5200; thiol groups, such as the products sold under the names "GP 72 A” and "GP 71" from Genesee; alkoxylated groups, such as the product sold under the name "Silicone Copolymer F-755" by SWS Silicones and Abil Wax ® 2428, 2434 and 2440 by Goldschmidt ; hydroxylated groups, such as the polyorganosiloxanes possessing a hydroxyal
  • polymers of the grafted silicone type comprising a polysiloxane portion and a portion comprising a non- silicone organic chain, one of the two portions constituting the main chain of the polymer and the other being grafted to the main chain.
  • These polymers are disclosed, for example, in the documents EP A 0 412 704, EP-A-O 412 707, EP-A-O 640 105, WO 95/00578, EP-A-O 582 152 and WO 93/23009 and Patents US Nos 4 693 935, 4 728 571 and 4 972 037.
  • These polymers are, for example, anionic or nonionic.
  • Such polymers are, for example, copolymers capable of being obtained by radical polymerization starting from the mixture of monomers comprising: a) approximately 50% to approximately 90% by weight of tert-butyl acrylate; b) 0% to approximately 40% by weight of acrylic acid; c) approximately 5% to approximately 40% by weight of silicone macromer of formula (VII) :
  • grafted silicone polymers are in particular polydimethylsiloxanes (PDMS) to which are grafted, via a connecting link of thiopropylene type, mixed polymer units of the poly ( (meth) acrylic acid) type and of the poly(alkyl (meth) acrylate) type and polydimethylsiloxanes (PDMS) to which are grafted, via a connecting link of thiopropylene type, polymer units of the poly (isobutyl (meth) acrylate) type.
  • PDMS polydimethylsiloxanes
  • the silicone is an aminated silicone.
  • aminated silicone is understood to mean, within the meaning of the present invention, any silicone comprising at least one primary, secondary or tertiary amine functional group or one quaternary ammonium group.
  • aminated silicones used in the composition in the film form according to the present invention are chosen from: (a) the compounds corresponding to the following formula (II) : (T) 3 - a - (R 1 Ja (H) in which formula (II) : o T, which are identical or different, are a hydrogen atom, a phenyl radical, a hydroxyl (-0H) radical, a linear or branched Ci-Cs alkyl radical, preferably a methyl radical, or a Ci-Cs alkoxy radical, preferably a methoxy radical, o a denotes the number 0 or a number from 1 to 3, and preferably 0, o b denotes 0 or 1, and in particular 1, o m and n, which are identical or different, are numbers such that the sum (n + m) can vary in particular from 1 to 2000 inclusive and in particular from 50 to 150 inclusive, it being possible for n to denote a number ranging from 0 to 1999 inclusive and in particular from 49
  • R 2 which are identical or different, can denote a hydrogen atom, a phenyl, a benzyl or a saturated monovalent hydrocarbon radical, for example a Ci-C 2 O alkyl radical, and Q ⁇ represents an anionic counterion of halide type, such as, for example, fluoride, chloride, bromide or iodide.
  • aminated silicones corresponding to the definition of the formula (II) are chosen from the compounds corresponding to the following formula (III) :
  • Ci-C 4 alkoxy radical preferably a methoxy radical; or OH;
  • A represents a linear or branched C3-C8, preferably
  • C3-C6, alkylene radical ; m and n are numbers depending on the molecular weight, the sum of which is between 1 and 2000 inclusive .
  • R, R' and R" which are identical or different, represent a linear or branched Ci-C 4 alkyl or hydroxyl radical
  • A represents a C3 alkylene radical and m and n are such that the weight-average molecular weight of the compound is between 5000 and 500 000 approximately.
  • the compounds of this type are named "amodimethicone" in the CTFA dictionary.
  • R, R' and R" which are identical or different, represent a linear or branched Ci-C 4 alkoxy or hydroxyl radical, at least one of the R or R" radicals is an alkoxy radical and A represents a C3 alkylene radical.
  • the hydroxyl/alkoxy molar ratio is preferably between 0.2/1 and 0.4/1 and is advantageously equal to 0.3/1.
  • n and n are such that the weight- average molecular weight of the compound is between 2000 and 1 000 000. More particularly, n is between 0 and 1500 inclusive and m is between 1 and 1000 inclusive, the sum of n and m being between 1 and 1800 inclusive .
  • Wacker-Belsil ADM LOG 1 corresponding to the mixture as a microemulsion of i) Amodimethicone, ii) Trideceth-5 and iii) Trideceth-10.
  • R and R" which are different, represent a linear or branched Ci-C 4 alkoxy or hydroxyl radical, at least one of the R or R" radicals is an alkoxy radical, R' represents a methyl radical and A represents a C3 alkylene radical.
  • the hydroxyl/alkoxy molar ratio is preferably between 1/0.8 and 1/1.1 and is advantageously equal to 1/0.95.
  • m and n are such that the weight-average molecular weight of the compound is between 2000 and 200 000 inclusive. More particularly, n is between 0 and 1500 inclusive and m is between 1 and 1000 inclusive, the sum of n and m being between 1 and 1800 inclusive .
  • the molecular weight of these silicones is determined by gel permeation chromatography (ambient temperature; polystyrene standard; styragem ⁇ columns; eluent THF; flow rate of 1 mm/m; 200 ⁇ l of a 0.5% by weight solution of silicone in THF are injected and detection is carried out by refractometry and UV spectrometry) .
  • a product corresponding to the definition of the formula (II) is in particular the polymer named "trimethylsilylamodimethicone" in the CTFA dictionary, corresponding to the following formula (IV) :
  • formula (IV) n and m have the meanings given above in accordance with the formula (II) .
  • Such compounds are described, for example, in EP 95 238; a compound of formula (II) is, for example, sold under the name Q2-8220 by OSI.
  • o R represents a monovalent Ci-Cis hydrocarbon radical and in particular a linear or branched Ci- Ci8 alkyl radical or a linear or branched C2-C18 alkenyl radical, for example a methyl or ethylenyl radical;
  • 0 Q " is an anionic counterion, such as halide, in particular chloride;
  • 0 r represents a mean statistical value between 2 and 20 inclusive and in particular between 2 and 8 inclusive;
  • 0 s represents a mean statistical value between 20 and 200 inclusive and in particular between 20 and 50 inclusive. Such compounds are described more particularly in
  • Patent US 4 185 087 Patent US 4 185 087.
  • Ci-Cis alkyl radical a linear or branched C2-C18 alkenyl radical or a ring comprising 5 or 6 carbon atoms, for example a methyl or ethylenyl radical
  • 0 R 6 represents a divalent hydrocarbon radical, in particular a linear or branched Ci-Cis alkylene radical, or a linear or branched divalent C1-C18, for example Ci-Cs, alkyleneoxy radical connected to the Si via an SiC bond
  • 0 R 8 which are identical or different, represent a hydrogen atom, a monovalent hydrocarbon radical having from 1 to 18 carbon atoms, in particular a linear or branched Ci-Cis alkyl radical or a linear or branched C2-C18 alkenyl radical, or an -R 6 -NHCOR 7 radical with R 6 and R7 as defined above
  • 0 Q " which are identical or different, represent an anionic counterion, such as halide, in particular chloride, or an organic acid
  • silicones are, for example, described in Application EP-A-O 530 974.
  • the silicones are liquid, i.e. liquid at ambient temperature (25°C) and at atmospheric pressure (760 mm of mercury), and insoluble in water under these conditions, that is to say with a solubility of less than 5% by weight, preferably of less than 1% by weight and more preferably still of less than 0.1% by weight in water. More particularly, the silicones are liquids and are oils.
  • the silicone or silicones used in the composition according to the invention can be present in an amount varying from 0.01 to 20% by weight, preferably in an amount varying from 0.1 to 15% by weight and more preferably still in an amount varying from 0.1 to 10% by weight, with respect to the total weight of the composition .
  • the ratio by weight of the compound of formula (I) or its salts to b) the silicone or silicones in accordance with the invention is between 0.005 and 20 and more preferably still between 0.01 and 10, better still between 0.05 and 1.
  • the other oxidation dyes can comprise one or more couplers conventionally used for the dyeing of keratinous fibres.
  • couplers Mention may in particular be made, among these couplers, of meta-phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene couplers, heterocyclic couplers and their addition salts.
  • 3-ureidoaniline 3-ureido-l- (dimethylamino) benzene, sesamol, 1- ( ⁇ -hydroxyethylamino) -3, 4-methylenedioxy- benzene, OC-naphthol, 2-methyl-l-naphthol, 1, 5-dihydroxynaphthalene, 2, 7-naphthalenediol,
  • the coupler or couplers if they are present, generally represent an amount of between 0.001 and 10% by weight approximately of the total weight of the dyeing composition, preferably between 0.005 and 6%.
  • the dyeing composition of the invention can optionally comprise one or more additional oxidation bases conventionally used for dyeing keratinous fibres other than the compound of formula (I) or its salts.
  • these additional oxidation bases are chosen from para-phenylenediamines other than the oxidation base of formula (I) and its addition salts, bisphenylalkylenediamines, para-aminophenols, bis-para-aminophenols, ortho-aminophenols or heterocyclic bases.
  • para-phenylenediamines by way of example, of para-phenylenediamine, para- toluenediamine, 2-chloro-para-phenylenediamine, 2,3- dimethyl-para-phenylenediamine, 2, 6-dimethyl-para- phenylenediamine, 2, 6-diethyl-para-phenylenediamine, 2, 5-dimethyl-para-phenylenediamine, N, N-dimethyl-para- phenylenediamine, N, N-diethyl-para-phenylenediamine, N, N-dipropyl-para-phenylenediamine, 4-amino-
  • N, N' -bis (4-aminophenyl) tetramethylenediamine N, N' -bis (4-methylaminophenyl) tetramethylenediamine, N, N' -bis (ethyl) -N, N' -bis (4' -amino-3' -methyl- phenyl) ethylenediamine, 1, 8-bis (2, 5-diaminophenoxy) - 3, 6-dioxaoctane and their addition salts with an acid.
  • para-aminophenols Mention may be made, among para-aminophenols, by way of example, of para-aminophenol, 4-amino- 3-methylphenol, 4-amino-3-fluorophenol, 4-amino- 3- (hydroxymethyl) phenol, 4-amino-2-methylphenol, 4-amino-2- (hydroxymethyl) phenol, 4-amino-2- (methoxy- methyl) phenol, 4-amino-2- (aminomethyl) phenol, 4-amino- 2- ( ( ⁇ -hydroxyethyl) aminomethyl) phenol, 4-amino-
  • heterocyclic bases by way of example, of pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
  • pyridine derivatives of the compounds described, for example, in Patents GB 1 026 978 and GB 1 153 196, such as 2, 5-diaminopyridine, 2- [ (4-methoxyphenyl) amino] - 3-aminopyridine, 2, 3-diamino-6-methoxypyridine,
  • pyrimidine derivatives of the compounds described, for example, in Patents DE 2 359 399; JP 88-169571; JP 05-63124; EP 0 770 375 or Patent Application WO 96/15765, such as 2,4,5, 6-tetraaminopyrimidine, 4-hydroxy-2, 5, 6-triamino- pyrimidine, 2-hydroxy-4, 5, 6-triaminopyrimidine, 2 , 4-dihydroxy-5, 6-diaminopyrimidine or 2, 5, 6-triaminopyrimidine, and pyrazolopyrimidine derivatives, such as those mentioned in Patent Application FR-A-2 750 048 and among which may be mentioned pyrazolo [ 1 , 5-a] - pyrimidine-3, 7-diamine; 2, 5-dimethylpyrazolo [1, 5-a] - pyrimidine-3, 7-diamine; pyrazolo [ 1, 5-a] pyrimidine- 3, 5-diamine; 2 , 7-
  • pyrazole derivatives of the compounds described in Patents DE 3 843 892 and DE 4 133 957 and Patent Applications WO 94/08969, WO 94/08970, FR-A-2 733 749 and DE 195 43 988, such as 4, 5-diamino-l-methylpyrazole, 4, 5-diamino-l- ( ⁇ -hydroxy- ethyl) pyrazole, 3, 4-diaminopyrazole, 4, 5-diamino-l- (4' - chlorobenzyl) pyrazole, 4, 5-diamino- 1 , 3-dimethylpyrazole, 4, 5-diamino-3-methyl-
  • the addition salts of the oxidation bases and couplers which can be used in the context of the invention are chosen in particular from the addition salts with an acid, such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulphonates, phosphates and acetates, and the addition salts with a base, such as sodium hydroxide, potassium hydroxide, aqueous ammonia, amines or alkanolamines .
  • an acid such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulphonates, phosphates and acetates
  • a base such as sodium hydroxide, potassium hydroxide, aqueous ammonia, amines or alkanolamines.
  • the composition comprises one or more additional oxidation bases
  • the latter more particularly represent (s) from 0.0005 to 12% by weight, with respect to the total weight of the dyeing composition, preferably from 0.005 to 8% by weight.
  • the dyeing composition in accordance with the invention can additionally comprise one or more direct dyes which can in particular be chosen from nitrobenzene dyes, azo direct dyes or methine direct dyes. These direct dyes can be nonionic, anionic or cationic in nature.
  • the direct dye or dyes, if they are present generally represent an amount of between 0.001 and 20% by weight, with respect to the total weight of the dyeing composition, preferably between 0.01 and 10% by weight.
  • the medium appropriate for dyeing also referred to as dyeing vehicle, generally comprises water or a mixture of water and of one or more solvents, such as, for example, lower Ci-C 4 alkanols, such as ethanol and isopropanol, polyols, such as propylene glycol, dipropylene glycol or glycerol, and polyol ethers, such as dipropylene glycol monomethyl ether.
  • solvents such as, for example, lower Ci-C 4 alkanols, such as ethanol and isopropanol
  • polyols such as propylene glycol, dipropylene glycol or glycerol
  • polyol ethers such as dipropylene glycol monomethyl ether.
  • the solvent or solvents are generally present in proportions which can be between 1 and 40% by weight approximately, with respect to the total weight of the dyeing composition, and more preferably still between 3 and 30% by weight approximately.
  • the dyeing composition in accordance with the invention can also include various adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or their mixtures, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or their mixtures, inorganic or organic thickening agents and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetration agents, sequestering agents, fragrances, buffers, dispersing agents, conditioning agents other than fatty substances a) or b) as defined above, modified or unmodified, film-forming agents, ceramides, preservatives or opacifying agents.
  • the above adjuvants are generally present in an amount, for each of them, of between 0.01 and 20% by weight, with respect to the weight of the composition.
  • the pH of the dyeing composition in accordance with the invention is generally between 3 and 12 approximately and preferably between 5 and 11 approximately. It can be adjusted to the desired value using acidifying or basifying agents commonly used in the dyeing of keratinous fibres or else by means of conventional buffering systems.
  • inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids, such as acetic acid, tartaric acid, citric acid or lactic acid, or sulphonic acids.
  • basifying agents by way of example, of aqueous ammonia, alkaline carbonates, alkanolamines, such as mono-, di- and triethanolamines and their derivatives, sodium hydroxide, potassium hydroxide and the compounds of following formula (VIII) :
  • W is a propylene residue optionally substituted by a hydroxyl group or a Ci-C 4 alkyl radical
  • R a , R b , R c and R d which are identical or different, represent a hydrogen atom or a Ci-C 4 alkyl or Ci-C 4 hydroxyalkyl radical.
  • composition according to the invention can comprise one or more oxidizing agents.
  • the oxidizing agents conventionally used for the oxidation dyeing of keratinous fibres are, for example, hydrogen peroxide, urea hydrogen peroxide, persalts, such as perborates and persulphates, peracids, alkali metal bromates and oxidase enzymes, among which may be mentioned peroxidases, 2-electron oxidoreductases, such as uricases, and 4-electron oxygenases, such as laccases. Hydrogen peroxide is particularly preferred.
  • the dyeing composition according to the invention can be provided in various forms, such as in the form of liquids, of creams or of gels or in any other form appropriate for carrying out dyeing of keratinous fibres, in particular of human hair.
  • compositions can result from the mixing at the time of use of several compositions.
  • it results from the mixing of at least two compositions, one comprising one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid, optionally one or more additional oxidation bases other than the compound of formula (I) or its salts and optionally one or more couplers, a second composition comprising the non-silicone liquid fatty substance or substances described above and optionally a third composition comprising one or more oxidizing agents as described above.
  • compositions one comprising one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid, the non-silicone liquid fatty substance or substances described above, optionally one or more additional oxidation bases other than the compound of formula (I) or its salts and optionally one or more couplers and the other comprising one or more oxidizing agents as described above.
  • composition of the invention is thus applied to the hair for the colouring of the keratinous fibres either as is or in the presence of one or more oxidizing agents for the colouring of the keratinous fibres .
  • the method of the present invention is a method in which the composition devoid of oxidizing agent according to the present invention as defined above is applied to the fibres, either alone or in the presence of one or more oxidizing agents, for a time sufficient to develop the desired colouring.
  • the colour can be developed at acidic, neutral or alkaline pH.
  • the oxidizing agent if it is present, can be added to the composition of the invention only at the time of use or it can be employed starting from an oxidizing composition comprising it, applied simultaneously with or sequentially to the composition of the invention.
  • the composition devoid of oxidizing agent according to the present invention is mixed, preferably at the time of use, with a composition comprising, in a medium appropriate for dyeing, one or more oxidizing agents.
  • the mixture obtained is subsequently applied to the keratinous fibres.
  • the oxidizing agents are those indicated above.
  • the temperature during the application of the composition is conventionally between ambient temperature (between 15 and 25°C) and 80 0 C, preferably between ambient temperature and 60 0 C.
  • the keratinous fibres are rinsed, washed with a shampoo, rinsed again and then dried.
  • the oxidizing composition can also include various adjuvants conventionally used in compositions for dyeing the hair and as defined above.
  • the pH of the oxidizing composition including the oxidizing agent is such that, after mixing with the dyeing composition, the pH of the resulting composition applied to the keratinous fibres preferably varies between 3 and 12 approximately and more preferably still between 5 and 11. It can be adjusted to the desired value using acidifying or basifying agents commonly used in the dyeing of keratinous fibres and as defined above.
  • the ready-for-use composition, with or without oxidizing agent, which is finally applied to the keratinous fibres can be provided in various forms, such as in the form of liquids, creams or gels or in any other form appropriate for carrying out dyeing of keratinous fibres and in particular of human hair.
  • the dyeing kit or multicompartment device :
  • a subject-matter of the invention is a dyeing kit or multicompartment device in which a first compartment includes the dyeing composition devoid of oxidizing agent of the present invention as defined above and a second compartment includes one or more oxidizing agents as described above.
  • a second device is composed of a first compartment, comprising a composition comprising one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid as described above, optionally one or more additional oxidation bases other than the compound of formula (I) or its salts as described above and optionally one or more couplers as described above, and a second compartment, comprising a composition comprising a) the non-silicone liquid fatty substance or substances or b) the silicone or silicones as described above.
  • a third device can optionally comprise the two compartments of the second device plus a third compartment including a composition comprising one or more oxidizing agents.
  • These devices can be equipped with a means allowing the desired product to be deposited on the hair, such as the devices described in Patent FR-2 586 913 on behalf of the Applicant Company.
  • composition A2 Composition A2
  • Example 1 For Example 1 :
  • composition (Cl) - 1 part by weight of the composition (Cl) and - 10 parts by weight of an aqueous oxidizing composition comprising 6% of hydrogen peroxide at a pH of 2.3 (B) ;
  • Example 2 - 9 parts by weight of the composition (A2) with
  • Each of these mixtures was applied to natural grey hair comprising 90% white hairs, at the rate of 10 g per 1 g of hair, for 30 minutes at ambient temperature.
  • the hair was subsequently rinsed, washed with a standard shampoo and dried.
  • the hair colouring was evaluated (height of tone and highlight) visually:
  • composition 4 is prepared:
  • Each of Composition 3 or Composition 4 is diluted at the time of use with 1.5 times its weight of 20 volume aqueous hydrogen peroxide solution.
  • the mixture thus prepared is applied at ambient temperature to natural grey hair comprising 90% white hairs, at the rate of 10 g per 1 g of hair, for 30 min for Composition 3 and 20 min for Composition 4.
  • the hair colourings were evaluated visually.

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Abstract

L'invention concerne une composition de coloration qui comprend au moins une base d'oxydation para-phénylènediamine secondaire spécifique et une substance grasse sélectionnée parmi a) des liquides sans silicone et b) des silicones. L'invention concerne également l'utilisation de ladite composition pour colorer des fibres de kératine et le procédé de coloration faisant intervenir cette composition. L'invention concerne en outre un dispositif à compartiments multiples. La composition de la présente invention permet en particulier d'obtenir une coloration à teintes variées, intenses et/ou chromatiques, attrayantes et faiblement sélectives, et qui présente une haute résistance aux diverses attaques auxquelles les cheveux peuvent être soumis.
PCT/EP2010/056784 2009-05-19 2010-05-18 Composition de coloration comprenant une base d'oxydation para-phénylènediamine secondaire et une substance grasse avec du silicone ou une substance grasse liquide sans silicone Ceased WO2010133575A2 (fr)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
FR0953319A FR2945730B1 (fr) 2009-05-19 2009-05-19 Composition tinctoriale comprenant une base d'oxydation para-phenylene diamine secondaire et un corps gras liquide non silicone.
FR0953322A FR2945731B1 (fr) 2009-05-19 2009-05-19 Composition tinctoriale comprenant une base d'oxydation para-phenylene diamine secondaire et une silicone.
FR0953322 2009-05-19
FR0953319 2009-05-19
US18019609P 2009-05-21 2009-05-21
US61/180,196 2009-05-21
US18177509P 2009-05-28 2009-05-28
US61/181,775 2009-05-28

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WO2014095458A3 (fr) * 2012-12-18 2014-10-09 Henkel Ag & Co. Kgaa Révélateur diphasique pour des produits modificateurs de couleur par oxydation
WO2014053504A3 (fr) * 2012-10-02 2014-10-23 L'oreal Agent permettant de modifier la couleur des fibres de kératine contenant un corps gras et polymère modificateur de rhéologie dans un système d'émulsion
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
US8920521B1 (en) 2013-10-01 2014-12-30 L'oreal Agent for altering the color of keratin fibers comprising a rheology modifying polymer and high levels of a fatty substance in a cream system
US9012691B2 (en) 2012-10-26 2015-04-21 The Procter & Gamble Company Process for preparing primary intermediates for dyeing keratin fibers
US9309185B2 (en) 2012-10-26 2016-04-12 The Procter & Gamble Company Process for preparing primary intermediates for dyeing keratin fibers
US9539192B2 (en) 2014-04-02 2017-01-10 Noxell Corporation Hair colouring compositions, kits, method, and use thereof
US9587116B2 (en) 2014-11-04 2017-03-07 Noxell Corporation Azo direct dyes and method for dyeing hair using these dyes
US9688609B2 (en) 2014-11-04 2017-06-27 Noxell Corporation Telescoping synthesis of 2-methoxymethyl-P-phenylenediamine
US9695109B2 (en) 2014-11-04 2017-07-04 Noxell Corporation Telescoping synthesis of 2-methoxymethyl-p-phenylenediamine
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CN110650627A (zh) * 2017-02-24 2020-01-03 牡蛎壳公司 甲硅烷基化的多元醇及其组合物

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US8663341B2 (en) 2012-06-25 2014-03-04 The Procter & Gamble Company Hair colorant compositions comprising 2-Methoxymethy1-1,4-diaminobenzene, methods, and kits comprising the compositions
US8702814B2 (en) 2012-06-25 2014-04-22 The Procter & Gamble Company Hair colorant compositions comprising 2-methoxymethyl-1,4-diaminobenzene and 2,6-diaminopyridine, methods, and kits comprising the compositions
US8709100B2 (en) 2012-06-25 2014-04-29 The Procter & Gamble Company Hair colorant compositions comprising 2-methoxymethyl-1,4-diaminobenzene and 5-amino-4-chloro-o-cresol, methods, and kits comprising the compositions
JP2015531385A (ja) * 2012-10-02 2015-11-02 ロレアル エマルジョン系中の脂肪性物質およびレオロジー調整ポリマーを含有するケラチン繊維の色を変更するための薬剤
CN104684533B (zh) * 2012-10-02 2018-01-05 欧莱雅 用于改变角蛋白纤维颜色的乳液体系中含有脂族物质和流变改性聚合物的试剂
WO2014053504A3 (fr) * 2012-10-02 2014-10-23 L'oreal Agent permettant de modifier la couleur des fibres de kératine contenant un corps gras et polymère modificateur de rhéologie dans un système d'émulsion
US9012691B2 (en) 2012-10-26 2015-04-21 The Procter & Gamble Company Process for preparing primary intermediates for dyeing keratin fibers
US9309185B2 (en) 2012-10-26 2016-04-12 The Procter & Gamble Company Process for preparing primary intermediates for dyeing keratin fibers
WO2014095458A3 (fr) * 2012-12-18 2014-10-09 Henkel Ag & Co. Kgaa Révélateur diphasique pour des produits modificateurs de couleur par oxydation
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
US8920521B1 (en) 2013-10-01 2014-12-30 L'oreal Agent for altering the color of keratin fibers comprising a rheology modifying polymer and high levels of a fatty substance in a cream system
US9539192B2 (en) 2014-04-02 2017-01-10 Noxell Corporation Hair colouring compositions, kits, method, and use thereof
US9688609B2 (en) 2014-11-04 2017-06-27 Noxell Corporation Telescoping synthesis of 2-methoxymethyl-P-phenylenediamine
US9695109B2 (en) 2014-11-04 2017-07-04 Noxell Corporation Telescoping synthesis of 2-methoxymethyl-p-phenylenediamine
US9758469B2 (en) 2014-11-04 2017-09-12 Noxell Corporation Process for the preparation of 2-substituted-1,4-benzenediamines and salts thereof
US9587116B2 (en) 2014-11-04 2017-03-07 Noxell Corporation Azo direct dyes and method for dyeing hair using these dyes
CN110650627A (zh) * 2017-02-24 2020-01-03 牡蛎壳公司 甲硅烷基化的多元醇及其组合物

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