Classifications

• • 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
  • A61K8/40—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
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
• • 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
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
  • A61K8/4913—Cosmetics 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
• • 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
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
  • A61K8/4913—Cosmetics 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
  • A61K8/492—Cosmetics 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 having condensed rings, e.g. indol
• • 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
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
  • A61K8/4926—Cosmetics 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

Definitions

• the subject of the invention is a composition for the oxidation dyeing of keratin fibers, and in particular human keratin fibers such as the hair comprising, in a medium suitable for dyeing, at least one oxidation base chosen from certain derivatives. substituted paraphenylenediamine and their addition salts with an acid and at least one particular synthetic direct dye and / or a natural dye, as well as the dyeing process using this composition.
• oxidation bases it is known to dye keratin fibers and in particular human hair with dye compositions containing oxidation dye precursors, in particular ortho or paraphenylenediamines, ortho or paraaminophenois, heterocyclic bases, generally called oxidation bases.
• oxidation dye precursors in particular ortho or paraphenylenediamines, ortho or paraaminophenois, heterocyclic bases, generally called oxidation bases.
• the precursors of oxidation dyes, or oxidation bases are colorless or weakly colored compounds which, associated with oxidizing products, can give rise, through an oxidative condensation process, to colored and coloring compounds.
• the so-called "permanent" coloration obtained thanks to these oxidation dyes must moreover satisfy a certain number of requirements. Thus, it must make it possible to obtain nuances in the desired intensity and present good resistance to external agents (light, bad weather, washing, permanent waving, perspiration, friction).
• the dyes must also make it possible to cover white hair, and finally be the least selective possible, that is to say allow to obtain the smallest possible color differences throughout the same keratin fiber, which can be in differently sensitized effect (ie damaged) between its tip and its root.
• compositions for the oxidation dyeing of keratin fibers containing, as dye precursors d oxidation, substituted derivatives of paraphenylenediamine.
• the colorings obtained by using these compositions are not always powerful enough, chromatic, or resistant to the various aggressions that the hair can undergo.
• oxidation dyes capable of leading to colorations with varied shades, chromatic, powerful, aesthetic, not very selective, and resistant well to the various aggressions that can undergo the fibers, by combining at least one oxidation base chosen from certain derivatives of paraphenylenediamine of formula (I) defined below and their addition salts with an acid and at least one particular direct dye and / or a dye natural.
• the first object of the invention is therefore a composition for the oxidation dyeing of keratin fibers and in particular human keratin fibers such as the hair, characterized in that it comprises, in a suitable medium for dyeing: - ( A) at least one oxidation base chosen from substituted derivatives of paraphenylenediamine of formula (I) below, and their addition salts with an acid: in which :
• Ri and R 2 can take one of the following meanings i) to v):
• R T and R 2 simultaneously represent a radical - (CH 2 ) 2 CHOHCH 2 OH; or ii) Ri represents a radical -CH 2 (CHOH) CH 2 OH and R 2 represents a hydrogen atom, an alkyl radical, aryl or a heterocycle; or ili) R ⁇ represents an alkyl, aryl or heterocycle radical and R 2 represents an alkylene radical - (CH 2 ) m - in which m is an integer equal to 2 or 3, said alkylene radical forming a ring together with nitrogen atom, the carbon atom of the benzene ring carrying the nitrogen atom and one of the two carbon atoms of the benzene ring which are adjacent to it, it being understood that when R 1 is an alkyl or aryl radical, then either R 1 or said alkylene radical is substituted by a radical containing at least one nitrogen, oxygen or sulfur atom; iv) R ⁇ represents a radical - (CH 2 CH 2 0) p R
• R 3 represents a halogen atom, an alkyl or aryl radical, a cyano, nitro, hydroxyl, carboxyl, sulfo, alkoxy, aryloxy, cyanoamino, amino, anilino, ureido, sulfamylamino, mono- or di-alkylsulfamylamino, alkylthio radical , arylthio, alkoxycarbonylamino, sulfonamido, carbamyl, mono- or di-alkylcarbamylsulfamyle, sulfonyl, alkoxycarbonyl, azo, acyloxy, carbamyloxy, mono- or di-alkylcarbamyloxy, silyl, silyloxy, aryloxycarbonylamino, imidoon, sulfonyl a heterocycle, a heterocycle linked to the benzene ring of formula (I)
• said alkyl radicals having from 1 to 25 carbon atoms and which may be linear, branched or cyclic and be substituted by one or more radicals and then represent a mono or polyhydroxyalkyl, alkoxyalkyl, aminoalkyl radical optionally substituted on the nitrogen atom, carboxyalkyl , alkylcarboxyalkyle, thioalkyle, alkylthioalkyle, cyanoalkyle, trifluoroalkyle, sulfoalkyle, phosphoalkyle, or haloalkyle; said alkoxy radicals having from 1 to 25 carbon atoms and which may be linear, branched or cyclic; said aryl radicals containing from 6 to 26 carbon atoms and which may be substituted by one or more radicals chosen from alkyl, substituted alkyl or alkoxy radicals; the heterocycles being mono or polycyclic, each cycle comprising 3, 4, 5 or 6 members and possibly containing one or more heteroatoms, it being understood
• - n is an integer between 0 and 4; it being understood that when n is greater than 1, then the radicals R 3 may be identical or different and form between them a saturated or unsaturated ring with 3, 4, 5, or 6 links;
• B at least one synthetic direct dye chosen from azo, quinonics, triarylmethanics, indoamines or azinics and / or a natural dye.
• the addition salts with an acid of the substituted para-phenylenediamine derivatives of formula (I) which can be used in dye compositions according to the invention are especially chosen from hydrochlorides, hydrobromides, sulphates, tartrates, lactates and acetates.
• the dye composition in accordance with the invention leads after mixing with an oxidizing composition, to colorings in various shades, chromatic, powerful, aesthetic, having a low selectivity and excellent resistance properties both to -vis atmospheric agents such as light and bad weather and vis-à-vis perspiration and different treatments that can undergo the hair.
• Another subject of the invention relates to a ready-to-use composition for the oxidation dyeing of keratin fibers which comprises, in a medium suitable for dyeing, at least one substituted derivative of paraphenylenediamine of formula (I), at least one azo, quinone, triarylmethane, indoamine or azine synthetic direct dye and / or a natural dye and at least one oxidizing agent.
• a ready-to-use composition for the oxidation dyeing of keratin fibers which comprises, in a medium suitable for dyeing, at least one substituted derivative of paraphenylenediamine of formula (I), at least one azo, quinone, triarylmethane, indoamine or azine synthetic direct dye and / or a natural dye and at least one oxidizing agent.
• ready-to-use composition is meant within the meaning of the present invention, any composition intended to be applied immediately to keratin fibers.
• the invention also relates to a process for the oxidation dyeing of keratin fibers, and in particular human keratin fibers such as the hair, consisting in applying to the fibers a coloring composition containing, in a medium suitable for dyeing, at least one substituted para-phenylenediamine derivative of formula (I) in combination with at least one synthetic azo, quinone, triarylmethane, indoamine or azine direct dye and / or a natural dye, the color being revealed at alkaline, neutral or acidic pH, using of a composition containing at least one oxidizing agent, which is mixed just at the time of use with the coloring composition or which is applied sequentially without intermediate rinsing.
• a coloring composition containing, in a medium suitable for dyeing, at least one substituted para-phenylenediamine derivative of formula (I) in combination with at least one synthetic azo, quinone, triarylmethane, indoamine or azine direct dye and / or
• the invention also relates to a dyeing device with several compartments or "kit” for the oxidation dyeing of keratin fibers, in particular of human keratin fibers such as the hair, which comprises at least one compartment containing at least one substituted derivative of paraphenylenediamine of formula (I) and at least one direct synthetic dye azo, quinonic, triarylmethane, indoaminic or azine and / or a dye natural, and at least one other compartment containing at least one oxidizing agent.
• kit for the oxidation dyeing of keratin fibers, in particular of human keratin fibers such as the hair, which comprises at least one compartment containing at least one substituted derivative of paraphenylenediamine of formula (I) and at least one direct synthetic dye azo, quinonic, triarylmethane, indoaminic or azine and / or a dye natural, and at least one other compartment containing at least one oxidizing agent.
• Another multi-compartment dyeing device comprises at least one compartment containing at least one substituted paraphenylenediamine derivative of formula (I), at least one compartment containing at least one synthetic azo, quinonic, triarylmethane, indoaminic or azine direct dye and / or a natural dye, and at least one other compartment containing at least one oxidizing agent.
• Ri and R 2 simultaneously represent a radical - (CH 2 ) 2CHOHCH 2 OH; or ii) Ri represents a radical -CH 2 (CHOH) 4 CH 2 OH and R 2 represents a hydrogen atom, an alkyl radical; or iv) R ⁇ represents a radical - (CH 2 CH 2 0) pR 4 in which p is an integer between 2 and 8 inclusive, R and R 2 , identical or different, represent a hydrogen atom, an alkyl radical ; v) Ri and R 2 form, together with the nitrogen atom to which they are attached, a saturated 5, 6 or 7-membered heterocycle, said heterocycle being substituted by at least one radical containing at least one carbon atom, or WO 01/66068 PCT / FR01 / 00644
• R 3 represents a halogen atom, an alkyl or aryl radical, a heterocycle,
• - n is an integer equal to 0, 1 or 2;
• Ri and R 2 form a pyrroiidinic heterocycle.
• the para-phenylenediamine derivative (s) of formula (I) used as oxidation base in the dye composition in accordance with the invention are present at concentrations varying from 0.0001 to 20%, preferably from 0.001 to 15% and even more particularly from 0.01 to 10% by weight relative to the total weight of the composition.
• the synthetic direct dyes which can be used according to the invention can be nonionic, anionic or cationic.
• natural dye is meant within the meaning of the invention, the compounds which exist in nature whether they have been obtained by extraction or reproduced via chemistry.
• natural direct dyes which can be used according to the invention, mention may be made of lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigo, isatin , curcumin, spinulosin, apigenidine.
• the synthetic direct dye (s) according to the invention and / or the natural dye (s) represent from 0.001 to 20% by weight approximately of the total weight of the composition and even more preferably from 0.005 to 10% by weight approximately.
• the compositions of the invention contain at least one coupler.
• couplers mention may in particular be made of metaphenylenediamines, meta-aminophenols, metadiphenols and heterocyclic couplers such as, for example, indole derivatives, indoline derivatives, benzimidazole derivatives, benzomorpholine derivatives, sesamol derivatives, pyridine, pyrimidine and pyrazole derivatives, and their addition salts with an acid.
• couplers are more particularly chosen from 2-methyl-5-amino-phenol, 5-N- ( ⁇ -hydroxyethyl) -amino2-methyl-phenol, 3-amino-phenol, 1,3-dihydroxy-benzene , 1, 3-dihydroxy-2-methyl-benzene, 4-chloro-1,3-dihydroxy-benzene, 2,4-diamino-1- ( ⁇ -hydroxyethyloxy) -benzene, 2-amino 4- ( ⁇ -hydroxyethylamino) -1-methoxy-benzene, 1, 3-diamino-benzene, 1, 3-bis- (2,4-diaminophenoxy) -propane, sesamol, 1-amino-2-methoxy- 4,5-methylenedioxy-benzene, ⁇ -naphthol, 2-methyl-1-naphthol, 6-hydroxy indole, 4-hydroxyindole, 4-hydroxy-N-methyl-indole, 6-hydroxy- indo
• the coupler (s) may be present in the said composition according to the invention at a concentration of between 0.0001 and 15% by weight relative to the total weight of the composition.
• the dye composition in accordance with the invention may, in addition, contain at least one additional oxidation base different from the substituted paraphenylenediamine derivatives of formula (I) and / or at least one direct dye different from those of the present invention.
• additional oxidation bases which can be used according to the invention, there may be mentioned paraphenylenediamine, paratoluylenediamine, 2-hydroxyethyl-paraphenylenediamine, 1-N, N-bis (2-hydroxyethyl) -paraphenylenediamine, para-aminophenols such as 3-methyl-4-aminophenol and 4-aminophenol, orthophenylenes diamines, orthoaminophenols, double bases, heterocyclic bases such as pyrimidines such as 2,4,5,6-tetraaminopyrimidine or as pyrazoles such as 1- (2-hydroxyethyl) -4,5-diamino-pyrazole.
• the additional oxidation base (s) may be present at a concentration of between 0.0001 and 15% by weight relative to the total weight of said composition.
• the medium of the composition suitable for dyeing is preferably an aqueous medium consisting of water and may advantageously contain cosmetically acceptable organic solvents, including more particularly alcohols such as ethyl alcohol, alcohol isopropyl, benzyl alcohol, and phenylethyl alcohol, or glycols or glycol ethers such as, for example, the monomethyl, monoethyl and monobutyl ethers of ethylene glycol, propylene glycol or its ethers such as, for example, the monomethyl ether of propylene glycol, butylene glycol, dipropylene glycol as well as the diethylene glycol alkyl ethers such as, for example, the monoethyl ether or the monobutyl ether of diethylene glycol, in concentrations of between approximately 1 and 40% and, preferably, between approximately 2 and 10% by weight per relative to the total weight of the composition.
• cosmetically acceptable organic solvents including more particularly alcohols such as ethyl alcohol, alcohol isopropyl, benz
• composition according to the invention may also contain an effective amount of other agents, also known previously in oxidation dyeing, such as various usual adjuvants such as sequestrants such as EDTA and etidronic acid, UV filters, waxes, silicones, volatile or not, cyclic or linear or branched, organomodified (in particular by amino groups) or not, preservatives, ceramides, pseudoceramides, vegetable, mineral or synthetic oils, vitamins or provitamins such as panthenol, opacifiers, thickening agents such as crosslinked polyacrylic acids or hydroxyalkylcelluloses, etc.
• agents also known previously in oxidation dyeing, such as various usual adjuvants such as sequestrants such as EDTA and etidronic acid, UV filters, waxes, silicones, volatile or not, cyclic or linear or branched, organomodified (in particular by amino groups) or not, preservatives, ceramides, pseudoceramides, vegetable, mineral or
• Said composition can also contain reducing or antioxidant agents. These can be chosen in particular from sodium sulfite, thioglycolic acid, thiolactic acid, sodium bisulfite, dehydroascorbic acid, hydroquinone, 2-methyl-hydroquinone, ter-butyl- hydroquinone and homogentisic acid, and they are then generally present in amounts ranging from approximately 0.05 to 1.5% by weight relative to the total weight of the composition.
• composition according to the invention may also contain one or more fatty alcohols, these fatty alcohols being introduced in pure form or as a mixture. Mention may be made among them more particularly of lauric, cetyl, stearyl and oleic alcohols and their mixtures. These fatty alcohols can represent from 0.001 to 20% by weight approximately of the total weight of the composition.
• the composition of the invention contains at least one nonionic, anionic, cationic or amphoteric surfactant in the proportion of about 0.1 to 20% by weight. Even more preferably, said composition contains at least one nonionic surfactant.
• composition according to the invention preferably contains at least one cationic or amphoteric substantive polymer in the proportion of approximately 0.05 to 10% by weight.
• the oxidizing agent is preferably chosen from hydrogen peroxide, urea peroxide, bromates or ferricyanides of alkali metals, persalts such as perborates and persulfates.
• the use of hydrogen peroxide is particularly preferred.
• This oxidizing agent advantageously consists of a solution of hydrogen peroxide, the titer of which can vary, more particularly, from approximately 1 to 40 volumes, and even more preferably from approximately 5 to 40.
• oxidizing agent one or more redox enzymes such as laccases, peroxidases and oxidoreductases with 2 electrons (such as uricase), where appropriate in the presence of their respective donor or cofactor.
• redox enzymes such as laccases, peroxidases and oxidoreductases with 2 electrons (such as uricase)
• the pH of the coloring composition or of the ready-to-use composition applied to the keratin fibers is generally between the values 4 and 12 It is preferably between 6 and 11, and can be adjusted to the desired value by means of acidifying or basifying agents well known from the state of the art in dyeing keratin fibers.
• basifying agents there may be mentioned, by way of example, ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamines as well as their derivatives, hydroxyalkylamines and ethylenediamines oxyethylenated and / or oxypropylenes, sodium or potassium hydroxides and the compounds of formula (II) below:
• W is a propylene residue optionally substituted by a hydroxyl group or an alkyl radical in CrC 4 ;
• R5, Re, R and R 8, identical or different, represent a hydrogen atom, an alkyl radical with C ⁇ -C 4 hydroxyalkyl or C ⁇ -C 4.
• the acidifying agents are conventionally, for example, mineral or organic acids such as hydrochloric acid, orthophosphoric acid, carboxylic acids such as tartaric acid, citric acid, lactic acid, or acids sulfonic.
• the dye composition in accordance with the invention can be in various forms, such as in the form of liquids, powders, creams, gels, optionally pressurized, or in any other form suitable for dyeing keratin fibers, and especially human hair.
• the dyeing process according to the invention preferably consists in applying the ready-to-use composition, produced extemporaneously at the time of use, from the coloring composition according to the invention and the oxidizing composition described above. , on the dry or wet keratin fibers, and to let it act for a pause time varying, preferably, from 1 to 60 minutes approximately, and more preferably from 10 to 45 minutes approximately, rinsing the fibers, then optionally wash with shampoo, then rinse again, and dry them.
• MA * stands for Active Matter At the time of use, the dye compositions described above were mixed weight for weight with a 20 volume hydrogen peroxide solution (6% by weight).
• the mixtures thus produced were applied for 30 minutes to locks of permanent natural gray hair containing 90% white hairs.
• the locks were then rinsed, washed with a standard shampoo, rinsed again and then dried.
• the hair was dyed in a purplish blue shade sustained from composition 1 and in a deep purple shade sustained from composition 2.

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• 2000
  • 2000-03-06 FR FR0002862A patent/FR2805741B1/fr not_active Expired - Fee Related
• 2001
  • 2001-03-05 AU AU2001240768A patent/AU2001240768A1/en not_active Abandoned
  • 2001-03-05 CA CA002400456A patent/CA2400456A1/fr not_active Abandoned
  • 2001-03-05 US US10/333,663 patent/US20030159221A1/en not_active Abandoned
  • 2001-03-05 BR BR0109021-6A patent/BR0109021A/pt not_active IP Right Cessation
  • 2001-03-05 JP JP2001564721A patent/JP2003528053A/ja active Pending
  • 2001-03-05 WO PCT/FR2001/000644 patent/WO2001066068A1/fr not_active Application Discontinuation
  • 2001-03-05 EP EP01911846A patent/EP1263397A1/de not_active Withdrawn

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