WO2010133639A1 - Dyeing composition comprising a secondary para-phenylenediamine oxidation base and a selected para-phenylenediamine or para-aminophenol oxidation base - Google Patents

Dyeing composition comprising a secondary para-phenylenediamine oxidation base and a selected para-phenylenediamine or para-aminophenol oxidation base Download PDF

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Publication number
WO2010133639A1
WO2010133639A1 PCT/EP2010/056896 EP2010056896W WO2010133639A1 WO 2010133639 A1 WO2010133639 A1 WO 2010133639A1 EP 2010056896 W EP2010056896 W EP 2010056896W WO 2010133639 A1 WO2010133639 A1 WO 2010133639A1
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formula
para
oxidation base
addition salts
acid
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PCT/EP2010/056896
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French (fr)
Inventor
Jean-Baptiste Saunier
Anne-Marie Couroux
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L'oreal
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Priority claimed from FR0953347A external-priority patent/FR2945736B1/en
Priority claimed from FR0953348A external-priority patent/FR2945737B1/en
Application filed by L'oreal filed Critical L'oreal
Publication of WO2010133639A1 publication Critical patent/WO2010133639A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • 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
    • A61K8/415—Aminophenols
    • 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

Definitions

  • One subject of the invention is a dyeing composition
  • a dyeing composition comprising at least one particular secondary para- phenylenediamine oxidation base and one particular para- phenylenediamine oxidation base or one particular para- aminophenol oxidation base and also the dyeing method employing this composition.
  • 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 condensation 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 unselective as possible, that is to say make it possible to obtain the smallest possible differences in colouring along the same keratin fibre, which is generally differently sensitized (i.e. damaged) between its tip and its root .
  • the aim of the present invention is to obtain a composition for colouring hair that exhibits enhanced dyeing properties in terms of intensity or chromaticity, and/or selectivity and/or resistance to external agents.
  • This aim is achieved with the present invention, one subject of which is a composition for dyeing keratin fibres comprising, in a suitable dyeing medium: one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid,
  • oxidation bases chosen from para- phenylenediamines of formula (II) or their addition salts with an acid , para-aminophenols of formula (III) or their addition salts with an acid: :
  • Ri which are identical or different, represent a hydrogen atom or a hydroxyethyl radical and R2 represents a hydrogen atom or a methyl radical
  • R represents a hydrogen atom or a methyl radical the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (II) when present being greater than 1 and the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (III) when present being from 0.2 to 20.
  • the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (II) is greater than 1 and up to 50 and better still is from 1.5 to 30.
  • the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (III) is from 0.5 to 10.
  • Another subject of the invention is a dyeing method using this composition.
  • composition of the present invention for dyeing keratin fibres, in particular human keratin fibres such as the hair.
  • the invention also relates to multicompartment devices comprising compositions employing one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid and one or more oxidation bases chosen from para- phenylenediamines of formula (II) or their addition salts with an acid, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (II) being greater than 1 in the mixture of compositions present in the various compartments and containing the compounds of formulae (I) and (II) .
  • the invention also relates to multicompartment devices comprising compositions employing one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid and one or more oxidation bases chosen from para- aminophenols of formula (III) or their addition salts with an acid, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (III) in the mixture of compositions containing the compounds of formula (I) and of formula (III) being greater than 0.2
  • the composition of the present invention makes it possible, in particular, to obtain a composition for colouring keratin fibres that is suitable for use in oxidation dyeing and that makes it possible to obtain a colouring with varied, intense or chromatic, attractive and not very selective shades which is highly resistant to the various attacks to which hair may be subjected such as shampoos, sweat, permanent deformations and light. It should be noted that in what follows, and unless otherwise indicated, that the limits of a range of values are included in this range
  • the compounds of formula (I) (II) or (III) may be in the form of addition salts especially chosen from the addition salts with an acid such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulphonates, phosphates and acetates. They may also be in the form of solvates, for example a hydrate, or a solvate of a linear or branched alcohol, such as ethanol or isopropanol.
  • the para- phenylenediamine oxidation base of formula (II) is chosen from para-phenylenediamine, para-toluenediamine, N,N-bis( ⁇ - hydroxyethyl) -para-phenylenediamine, or the corresponding addition salts with an acid.
  • the compounds of formula (II) are chosen from para- aminophenol, 3-methyl-4-aminophenol or their addition salts with an acid.
  • the compounds of formula (I) (II) or (III) are each generally present in an amount of between 0.001% and 10% by weight approximately and preferably between 0.005% and 6% by weight relative to the total weight of the dyeing composition.
  • the dyeing composition according to the invention may contain and preferably does contain one or more couplers conventionally used for dyeing keratin fibres.
  • couplers conventionally used for dyeing keratin fibres.
  • couplers mention may especially be made of meta- phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers, heterocyclic couplers, and the addition salts thereof.
  • couplers examples include 2-methyl- 5-aminophenol, 5-N- ( ⁇ -hydroxyethyl) amino-2-methylphenol, 6-chloro-2-methyl-5-aminophenol, 3-aminophenol, 2, 4-dichloro-3- aminophenol, 5-amino-4-chloro-o-cresol, 1, 3-dihydroxybenzene, 1, 3-dihydroxy-2-methylbenzene, 4-chloro-l, 3-dihydroxybenzene, 2, 4-diamino-l- ( ⁇ -hydroxyethyloxy) benzene, 2-amino-4- ( ⁇ - hydroxyethylamino) -1-methoxybenzene, 1, 3-diaminobenzene, 1,3- bis (2 , 4-diaminophenoxy) propane, 3-ureidoaniline, 3-ureido-l- dimethylaminobenzene, sesamol, l- ⁇ -hydroxyethylamino-3, 4- methylenedioxybenzene,
  • the coupler (s) is (are) each generally present in an amount of between 0.001% and 10% by weight approximately and preferably between 0.005% and 6% by weight relative to the total weight of the dyeing composition.
  • the dyeing composition of the invention may optionally comprise one or more additional oxidation bases conventionally used for dyeing keratin fibres other than the compounds of formula (I) (II) or (III) .
  • additional oxidation bases are chosen from para-phenylenediamines other than the bases of formula (I) or (II), bis (phenyl) alkylenediamines, para- aminophenols other than ones of formula (III), bis-para- aminophenols, ortho-aminophenols and heterocyclic bases, and the addition salts thereof.
  • para-phenylenediamines mention may be made, for example, of 2-chloro-para-phenylenediamine, 2, 3-dimethyl-para- phenylenediamine, 2, 6-dimethyl-para-phenylenediamine, 2,6- diethyl-para-phenylenediamine, 2, 5-dimethyl-para- phenylenediamine, N, N-dimethyl-para-phenylenediamine, N, N- diethyl-para-phenylenediamine, N, N-dipropyl-para- phenylenediamine, 4-amino-N, N-diethyl-3-methylaniline, 4-N,N- bis ( ⁇ -hydroxyethyl) amino-2-methylaniline, 4-N,N-bis ( ⁇ - hydroxyethyl) amino-2-chloroaniline, 2- ⁇ -hydroxyethyl-para- phenylenediamine, 2-fluoro-para-phenylenediamine, 2-chloro
  • the bis (phenyl) alkylenediamines mention may be made, for example, of N, N'-bis ( ⁇ -hydroxyethyl) -N, N' -bis (4'- aminophenyl) -1, 3-diaminopropanol, N, N'-bis ( ⁇ -hydroxyethyl) -N, N'- bis (4'-aminophenyl) ethylenediamine, N, N' -bis (4- aminophenyl) tetramethylenediamine, N, N' -bis ( ⁇ -hydroxyethyl) - N, N' -bis (4-aminophenyl) tetramethylenediamine, N, N' -bis (4- methylaminophenyl) tetramethylenediamine, N, N' -bis (ethyl) -N, N' - bis (4'-amino-3'-methylphenyl) ethylenediamine and l,8-bis(2,5
  • para-aminophenols mention may be made, for example, of 4-amino-3-fluorophenol, 4-amino-3-hydroxy- methylphenol, 4-amino-2-methylphenol, 4-amino-
  • ortho-aminophenols mention may be made, for example, of 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6- methylphenol and 5-acetamido-2-aminophenol, and the addition salts thereof with an acid.
  • heterocyclic bases mention may be made, for example, of pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
  • pyridine derivatives mention may be made of the compounds described, for example, in patents GB 1 026 978 and GB 1 153 196, such as 2, 5-diaminopyridine, 2- (4- methoxyphenyl) amino-3-aminopyridine, 2, 3-diamino-6- methoxypyridine, 2- ( ⁇ -methoxyethyl) amino-3-amino-6- methoxypyridine and 3, 4-diaminopyridine, and the addition salts thereof with an acid.
  • pyrimidine derivatives mention may be made of the compounds described, for example, in patents DE 2359399, 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-triaminopyrimidine, 2-hydroxy-4, 5, 6-triaminopyrimidine, 2 , 4-dihydroxy-5, 6-diaminopyrimidine and 2, 5, 6-triaminopyrimidine, and pyrazolopyrimidine derivatives such as those mentioned in patent application FR-A-2 750 048 and among which mention may be made of pyrazolo [ 1, 5-a] pyrimidine-3, 7-diamine;
  • diaminopyrazole bases mention may be made of the compounds described in patents DE-A-38 43 892 and DE-A-41 33 957 and patent applications WO 94/08969, WO 94/08970, FR-A- 2 733 749 and DE-A-195 43 988, such as 4, 5-diamino-l- methylpyrazole, 4, 5-diamino-l- (2-hydroxyethyl) pyrazole, 4,5- diamino-1- (4 ' -chlorobenzyl) pyrazole, 4 , 5-diamino-l , 3-dimethyl- pyrazole, 4, 5-diamino-3-methyl-l-phenylpyrazole, 4,5-diamino- l-methyl-3-phenylpyrazole, 4-amino-l, 3-dimethyl-
  • addition salts of the additional oxidation bases and of the couplers that may be used in the context of the invention are chosen especially from the addition salts with an acid, such as the 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, ammonium hydroxide, amines or alkanolamines .
  • an acid such as the hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulphonates, phosphates and acetates
  • a base such as sodium hydroxide, potassium hydroxide, ammonium hydroxide, amines or alkanolamines .
  • the dyeing composition in accordance with the invention may also contain one or more direct dyes which may, in particular, be chosen from nitrobenzene dyes, azo direct dyes or methine direct dyes. These direct dyes may be of nonionic, anionic or cationic nature.
  • the medium suitable for dyeing also known as dyeing vehicle, generally comprises water or a mixture of water and of one or more solvents such as, for example, C1-C4 lower alkanols, for instance 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, C1-C4 lower alkanols, for instance ethanol and isopropanol
  • polyols such as propylene glycol, dipropylene glycol or glycerol
  • polyol ethers such as dipropylene glycol monomethyl ether.
  • the solvent (s) is (are) in general present in proportions which may be between 1% and 40% by weight approximately, and more preferably between 3% and 30% by weight approximately, relative to the total weight of the dyeing composition.
  • the dyeing composition in accordance with the invention may also contain various adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof, inorganic or organic thickening agents and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrants, sequestrants, fragrances, buffers, dispersants, conditioning agents such as, for example, volatile or non-volatile, modified or unmodified silicones, 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 relative 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 may be adjusted to the desired value by using acidifying or basifying agents commonly used in the dyeing of keratin 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 mention may be made, by way of example, of aqueous ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamines and also derivatives thereof, sodium or potassium hydroxides and compounds of formula (III) below:
  • R a , R b , R c and R d which are identical or different, represent a hydrogen atom, a Ci-C 4 alkyl radical or a Ci-C 4 hydroxyalkyl radical.
  • composition according to the invention may comprise one or more oxidizing agents.
  • the oxidizing agents are those conventionally used for the oxidation dyeing of keratin fibres, which are, for example, hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulphates, peracids and oxidase enzymes, among which mention may be made of peroxidases, 2-electron oxidoreductases such as uricases and 4-electron oxygenases such as laccases. Hydrogen peroxide is particularly preferred.
  • composition with or without oxidizing agent according to the invention may be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratin fibres, and especially human hair.
  • compositions may result from the mixing of several compositions at the time of use.
  • 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 compounds of formula (I) or of formula (II) or salts thereof, and optionally one or more couplers, a second composition comprising the oxidation base(s) of formula (II) or their addition salts with an acid and optionally a third composition comprising one or more oxidizing agents as described previously, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (II) being greater than 1 in the mixture of the first two compositions.
  • compositions one comprising one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid, the oxidation base(s) of formula (II) or their addition salts with an acid, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula
  • 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 compounds of formula (I) or of formula (III) or salts thereof, and optionally one or more couplers, a second composition comprising the oxidation base(s) of formula (III) or salts thereof optionally one or more additional oxidation bases other than the compounds of formula (I) or of formula (III) or salts thereof, and optionally one or more couplers, the molar ratio, in the mixture of the two compositions, of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (III) being greater than 0.2, and optionally a third composition comprising one or more oxidizing agents as described previously.
  • compositions one comprising one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid, the oxidation base(s) of formula (III) or salts thereof, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (III) being greater than 0.2, optionally one or more additional oxidation bases other than the compounds of formula (I) or of formula (III) or salts thereof, and optionally one or more couplers, another composition comprising one or more oxidizing agents as described previously.
  • composition of the invention is therefore applied to the hair for colouring keratin fibres either as is, or in the presence of one or more oxidizing agents for colouring keratin fibres .
  • the method of the present invention is a method in which, applied to the fibres, is the composition without oxidizing agent according to the present invention as defined previously, either alone or in the presence of one or more oxidizing agents for a sufficient time to develop the desired colouring.
  • the colour may be developed at acid, neutral or alkaline pH and the oxidizing agent may be added to the composition of the invention only at the time of use or it may be used starting from an oxidizing composition containing it, applied simultaneously with or sequentially to the composition of the invention.
  • the composition without oxidizing agent according to the present invention is mixed, preferably at the time of use, with a composition containing, in a medium suitable for dyeing, one or more oxidizing agents.
  • the mixture obtained is then applied to the keratin fibres. After a leave-in time of 3 to 50 minutes approximately, preferably 5 to 30 minutes approximately, the keratin fibres are rinsed, optionally washed with shampoo, rinsed again, then dried.
  • the oxidizing agents are those indicated previously.
  • the oxidizing composition may also contain various additives conventionally used in compositions for dyeing hair and as defined previously.
  • the pH of the oxidizing composition containing the oxidizing agent is such that after mixing with the dyeing composition, the pH of the resulting composition applied to the keratin fibres preferably varies between 3 and 12 approximately, and more preferably still between 5 and 11. It may be adjusted to the desired value by means of acidifying or basifying agents customarily used in the dyeing of keratin fibres and as defined previously.
  • Another subject of the invention is a dyeing kit or multicompartment device in which a first compartment contains the dyeing composition without oxidizing agent of the present invention defined above comprising one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid and one or more oxidation bases chosen from the compounds of formula (II) or their addition salts with an acid, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (II) being greater than 1, and a second compartment contains one or more oxidizing agents .
  • a second device is constituted by a first compartment containing a composition 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 those of formula (I) or (II) or their addition salts with an acid, optionally one or more couplers and a second compartment containing a composition that comprises one or more oxidation bases chosen from the compounds of formula (II) or their addition salts with an acid and optionally one or more couplers, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (II) of the mixture of the compositions of the two compartments being greater than 1.
  • a third device may optionally comprise the two compartments from the second device plus a third compartment containing a composition that comprises one or more oxidizing agents.
  • the subject of the invention is also a dyeing kit or multicompartment device in which a first compartment contains the dyeing composition without oxidizing agent of the present invention defined above comprising one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid and one or more oxidation bases chosen from the compounds of formula (III) or their addition salts with an acid, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (III) being greater than 0.2, and a second compartment contains one or more oxidizing agents.
  • a first compartment contains the dyeing composition without oxidizing agent of the present invention defined above comprising one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid and one or more oxidation bases chosen from the compounds of formula (III) or their addition salts with an acid, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (III) being greater
  • a second device is constituted by a first compartment containing a composition 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 those of formula (I) or (III) or their addition salts with an acid, optionally one or more couplers and a second compartment containing a composition that comprises one or more oxidation bases chosen from the compounds of formula (III) or their addition salts with an acid, optionally one or more additional oxidation bases other than those of formula (I) or (III) or their addition salts with an acid, and optionally one or more couplers, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (III) being greater than 0.2.
  • a third device may optionally comprise the two compartments from the second device plus a third compartment containing a composition that comprises one or more oxidizing agents.
  • These devices may be equipped with a means that makes it possible to deliver the desired mixture to the hair, such as the devices described in patent FR-2 586 913 in the name of the applicant.
  • compositions Cl, C2 and C3 were prepared:
  • composition was diluted extemporaneously with 1 times its weight of 20-volume aqueous hydrogen peroxide solution.
  • Each of the mixtures was applied to grey hair containing 90% white hair in an amount of 10 g of mixture per 1 g of hair. After leaving in for 30 minutes at ambient temperature, the hair was then rinsed, washed with a standard shampoo and dried.
  • the hair colouring was evaluated visually.
  • compositions C4 and C5 were prepared
  • composition was diluted extemporaneously with 1 times its weight of 20-volume aqueous hydrogen peroxide solution.
  • the hair colouring was evaluated visually.

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Abstract

One subject of the present invention is a composition for dyeing keratin fibres comprising, in a suitable dyeing medium : - one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid, formula (I), and one or more oxidation bases chosen from para-phenylenediamines of formula (II) or their addition salts with an acid; para-aminophenols of formula (III) or their addition salts with an acid: formula (II), formula (II), wherein in formula (II) R1, which are identical or different, represent a hydrogen atom or a hydroxyethyl radical and R2 represents a hydrogen atom or a methyl radical, and wherein in formula (III) R represents a hydrogen atom or a methyl radical. The composition of the present invention makes it possible, in particular, to obtain a colouring with varied, intense and/or chromatic, attractive and not very selective shades which is highly resistant to the various attacks to which hair may be subjected.

Description

DYEING COMPOSITION COMPRISING A SECONDARY PARA-
PHENYLENEDIAMINE OXIDATION BASE AND A SELECTED PARA-
PHENYLENEDIAMINE or PARA-AMINOPHENOL OXIDATION BASE
One subject of the invention is a dyeing composition comprising at least one particular secondary para- phenylenediamine oxidation base and one particular para- phenylenediamine oxidation base or one particular para- aminophenol oxidation base and also the dyeing method employing this composition. It is known to dye keratin fibres, in particular human hair, with dyeing compositions containing oxidation dye precursors, generally known as oxidation bases, such as ortho- or para- phenylenediamines, ortho- or para-aminophenols and heterocyclic compounds. These oxidation bases are colourless or weakly coloured compounds which, in combination with oxidizing products, can give rise, by an oxidative condensation process, to coloured compounds.
It is also known that it is possible to vary the shades obtained with these oxidation bases by combining them with 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 variety of the molecules employed as oxidation bases and couplers makes it possible to obtain a rich palette of colours .
The "permanent" colouring obtained by virtue of these oxidation dyes furthermore has to satisfy a certain number of requirements. Thus, 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 unselective as possible, that is to say make it possible to obtain the smallest possible differences in colouring along the same keratin fibre, which is generally differently sensitized (i.e. damaged) between its tip and its root .
It is already known to use oxidation bases of para- phenylenediamine type in the field of colouring keratin fibres, especially secondary oxidation bases of formula (I) below for dyeing keratin fibres, especially the hair. In particular, such a base is disclosed in documents EP 1580184 and EP 0055386. This base has the drawbacks of resulting in colourings that are insufficiently intense or chromatic and/or that are too selective.
The aim of the present invention is to obtain a composition for colouring hair that exhibits enhanced dyeing properties in terms of intensity or chromaticity, and/or selectivity and/or resistance to external agents. This aim is achieved with the present invention, one subject of which is a composition for dyeing keratin fibres comprising, in a suitable dyeing medium: one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid,
Figure imgf000003_0001
and one or more oxidation bases chosen from para- phenylenediamines of formula (II) or their addition salts with an acid , para-aminophenols of formula (III) or their addition salts with an acid: :
Figure imgf000003_0002
wherein in formula (II) Ri, which are identical or different, represent a hydrogen atom or a hydroxyethyl radical and R2 represents a hydrogen atom or a methyl radical, and in formula (III) R represents a hydrogen atom or a methyl radical the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (II) when present being greater than 1 and the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (III) when present being from 0.2 to 20.
Preferably, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (II) is greater than 1 and up to 50 and better still is from 1.5 to 30.
Preferably the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (III) is from 0.5 to 10.
Another subject of the invention is a dyeing method using this composition.
Another subject of the invention is the use of the composition of the present invention for dyeing keratin fibres, in particular human keratin fibres such as the hair.
The invention also relates to multicompartment devices comprising compositions employing one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid and one or more oxidation bases chosen from para- phenylenediamines of formula (II) or their addition salts with an acid, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (II) being greater than 1 in the mixture of compositions present in the various compartments and containing the compounds of formulae (I) and (II) .
The invention also relates to multicompartment devices comprising compositions employing one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid and one or more oxidation bases chosen from para- aminophenols of formula (III) or their addition salts with an acid, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (III) in the mixture of compositions containing the compounds of formula (I) and of formula (III) being greater than 0.2 The composition of the present invention makes it possible, in particular, to obtain a composition for colouring keratin fibres that is suitable for use in oxidation dyeing and that makes it possible to obtain a colouring with varied, intense or chromatic, attractive and not very selective shades which is highly resistant to the various attacks to which hair may be subjected such as shampoos, sweat, permanent deformations and light. It should be noted that in what follows, and unless otherwise indicated, that the limits of a range of values are included in this range.
The compounds of formula (I) (II) or (III) may be in the form of addition salts especially chosen from the addition salts with an acid such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates, tosylates, benzenesulphonates, phosphates and acetates. They may also be in the form of solvates, for example a hydrate, or a solvate of a linear or branched alcohol, such as ethanol or isopropanol.
According to one particular embodiment, the para- phenylenediamine oxidation base of formula (II) is chosen from para-phenylenediamine, para-toluenediamine, N,N-bis(β- hydroxyethyl) -para-phenylenediamine, or the corresponding addition salts with an acid.
The compounds of formula (II) are chosen from para- aminophenol, 3-methyl-4-aminophenol or their addition salts with an acid. The compounds of formula (I) (II) or (III) are each generally present in an amount of between 0.001% and 10% by weight approximately and preferably between 0.005% and 6% by weight relative to the total weight of the dyeing composition.
The dyeing composition according to the invention may contain and preferably does contain one or more couplers conventionally used for dyeing keratin fibres. Among these couplers, mention may especially be made of meta- phenylenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers, heterocyclic couplers, and the addition salts thereof. Examples of couplers that may be mentioned include 2-methyl- 5-aminophenol, 5-N- (β-hydroxyethyl) amino-2-methylphenol, 6-chloro-2-methyl-5-aminophenol, 3-aminophenol, 2, 4-dichloro-3- aminophenol, 5-amino-4-chloro-o-cresol, 1, 3-dihydroxybenzene, 1, 3-dihydroxy-2-methylbenzene, 4-chloro-l, 3-dihydroxybenzene, 2, 4-diamino-l- (β-hydroxyethyloxy) benzene, 2-amino-4- (β- hydroxyethylamino) -1-methoxybenzene, 1, 3-diaminobenzene, 1,3- bis (2 , 4-diaminophenoxy) propane, 3-ureidoaniline, 3-ureido-l- dimethylaminobenzene, sesamol, l-β-hydroxyethylamino-3, 4- methylenedioxybenzene, OC-naphthol, 2-methyl-l-naphthol, 1,5- dihydroxynaphthalene, 2, 7-naphthalenediol, l-acetoxy-2- methylnaphthalene, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methy1indole, 2-amino-3-hydroxypyridine, 6-hydroxybenzomorpholine, 3, 5-diamino-2, 6-dimethoxypyridine, 2, 6-dihydroxy-3-4-dimethylpyridine, 3-amino-2-methylamino-6- methoxypyridine, 1-N- (β-hydroxyethyl) amino-3, 4-methylene- dioxybenzene, 2, 6-bis (β-hydroxyethylamino) toluene and 3-methy1- l-phenyl-5-pyrazolone, and the addition salts thereof with an acid.
In the composition of the present invention, the coupler (s) is (are) each generally present in an amount of between 0.001% and 10% by weight approximately and preferably between 0.005% and 6% by weight relative to the total weight of the dyeing composition.
The dyeing composition of the invention may optionally comprise one or more additional oxidation bases conventionally used for dyeing keratin fibres other than the compounds of formula (I) (II) or (III) . By way of example, these additional oxidation bases are chosen from para-phenylenediamines other than the bases of formula (I) or (II), bis (phenyl) alkylenediamines, para- aminophenols other than ones of formula (III), bis-para- aminophenols, ortho-aminophenols and heterocyclic bases, and the addition salts thereof.
Among the para-phenylenediamines, mention may be made, for example, of 2-chloro-para-phenylenediamine, 2, 3-dimethyl-para- phenylenediamine, 2, 6-dimethyl-para-phenylenediamine, 2,6- diethyl-para-phenylenediamine, 2, 5-dimethyl-para- phenylenediamine, N, N-dimethyl-para-phenylenediamine, N, N- diethyl-para-phenylenediamine, N, N-dipropyl-para- phenylenediamine, 4-amino-N, N-diethyl-3-methylaniline, 4-N,N- bis (β-hydroxyethyl) amino-2-methylaniline, 4-N,N-bis (β- hydroxyethyl) amino-2-chloroaniline, 2-β-hydroxyethyl-para- phenylenediamine, 2-fluoro-para-phenylenediamine, 2-isopropyl- para-phenylenediamine, N- (β-hydroxypropyl) -para-phenyl- enediamine, 2-hydroxymethyl-para-phenylenediamine, N, N- dimethyl-3-methyl-para-phenylenediamine, N-ethyl-N- (β- hydroxyethyl) -para-phenylenediamine, N- (β,γ-dihydroxypropyl) - para-phenylenediamine, N- (4' -aminophenyl) -para- phenylenediamine, N-phenyl-para-phenylenediamine,
2-β-hydroxyethyloxy-para-phenylenediamine, 2-β-acetylamino- ethyloxy-para-phenylenediamine, N- (β-methoxyethyl) -para- phenylenediamine, 4-aminophenylpyrrolidine, 2-thienyl-para- phenylenediamine, 2-β-hydroxyethylamino-5-aminotoluene and 3-hydroxy-l- (4' -aminophenyl) pyrrolidine, and the addition salts thereof with an acid. Among the para-phenylenediamines mentioned above, 2- isopropyl-para-phenylenediamine, 2-β-hydroxyethyl-para- phenylenediamine, 2-β-hydroxyethyloxy-para-phenylenediamine, 2, 6-dimethyl-para-phenylenediamine, 2, 6-diethyl-para- phenylenediamine, 2, 3-dimethyl-para-phenylenediamine, 2-chloro-para-phenylenediamine and 2-β-acetylaminoethyloxy- para-phenylenediamine, and the addition salts thereof with an acid are particularly preferred.
Among the bis (phenyl) alkylenediamines, mention may be made, for example, of N, N'-bis (β-hydroxyethyl) -N, N' -bis (4'- aminophenyl) -1, 3-diaminopropanol, N, N'-bis (β-hydroxyethyl) -N, N'- bis (4'-aminophenyl) ethylenediamine, N, N' -bis (4- aminophenyl) tetramethylenediamine, N, N' -bis (β-hydroxyethyl) - N, N' -bis (4-aminophenyl) tetramethylenediamine, N, N' -bis (4- methylaminophenyl) tetramethylenediamine, N, N' -bis (ethyl) -N, N' - bis (4'-amino-3'-methylphenyl) ethylenediamine and l,8-bis(2,5- diaminophenoxy) -3, 6-dioxaoctane, and the addition salts thereof with an acid.
Among the para-aminophenols, mention may be made, for example, of 4-amino-3-fluorophenol, 4-amino-3-hydroxy- methylphenol, 4-amino-2-methylphenol, 4-amino-
2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino- 2-aminomethylphenol, 4-amino-2- (β-hydroxyethyl- aminomethyl) phenol, 4-amino-2-fluorophenol, l-hydroxy-4- methylaminobenzene and 2, 2' -methylenebis (4-aminophenol) and the addition salts thereof with an acid.
Among the ortho-aminophenols, mention may be made, for example, of 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6- methylphenol and 5-acetamido-2-aminophenol, and the addition salts thereof with an acid.
Among the heterocyclic bases, mention may be made, for example, of pyridine derivatives, pyrimidine derivatives and pyrazole derivatives. Among the pyridine derivatives, mention may be made of the compounds described, for example, in patents GB 1 026 978 and GB 1 153 196, such as 2, 5-diaminopyridine, 2- (4- methoxyphenyl) amino-3-aminopyridine, 2, 3-diamino-6- methoxypyridine, 2- (β-methoxyethyl) amino-3-amino-6- methoxypyridine and 3, 4-diaminopyridine, and the addition salts thereof with an acid.
Among the pyrimidine derivatives, mention may be made of the compounds described, for example, in patents DE 2359399, 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-triaminopyrimidine, 2-hydroxy-4, 5, 6-triaminopyrimidine, 2 , 4-dihydroxy-5, 6-diaminopyrimidine and 2, 5, 6-triaminopyrimidine, and pyrazolopyrimidine derivatives such as those mentioned in patent application FR-A-2 750 048 and among which mention may be made of 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-dimethylpyrazolo-
[1, 5-a] pyrimidine-3, 5-diamine; 3-aminopyrazolo [1, 5-a] - pyrimidin-7-ol; 3-aminopyrazolo [1, 5-a] pyrimidin-5-ol; 2- (3- aminopyrazolo [ 1 , 5-a] pyrimidin-7-ylamino) ethanol, 2- (7- aminopyrazolo [1, 5-a] pyrimidin-3-ylamino) ethanol, 2- [ (3- aminopyrazolo [ 1 , 5-a] pyrimidin-7-yl) (2-hydroxyethyl) amino] - ethanol, 2- [ (7-aminopyrazolo [ 1, 5-a] pyrimidin-3-yl) (2- hydroxyethyl) amino] ethanol, 5, 6-dimethylpyrazolo [1, 5-a] - pyrimidine-3, 7-diamine, 2, 6-dimethylpyrazolo [1, 5-a] pyrimidine- 3, 7-diamine, 2 , 5, N7 , N7-tetramethylpyrazolo [ 1 , 5-a] pyrimidine- 3, 7-diamine and 3-amino-5-methyl-7-imidazolylpropylamino- pyrazolo [ 1, 5-a] pyrimidine, and the addition salts thereof with an acid and the tautomeric forms thereof, when a tautomeric equilibrium exists.
As examples of diaminopyrazole bases, mention may be made of the compounds described in patents DE-A-38 43 892 and DE-A-41 33 957 and patent applications WO 94/08969, WO 94/08970, FR-A- 2 733 749 and DE-A-195 43 988, such as 4, 5-diamino-l- methylpyrazole, 4, 5-diamino-l- (2-hydroxyethyl) pyrazole, 4,5- diamino-1- (4 ' -chlorobenzyl) pyrazole, 4 , 5-diamino-l , 3-dimethyl- pyrazole, 4, 5-diamino-3-methyl-l-phenylpyrazole, 4,5-diamino- l-methyl-3-phenylpyrazole, 4-amino-l, 3-dimethyl-
5-hydrazinopyrazole, l-benzyl-4, 5-diamino-3-methylpyrazole, 4, 5-diamino-3- tert-butyl-1-methylpyrazole, 4, 5-diamino-l- tert- butyl-3-methylpyrazole, 4, 5-diamino-l- (β-hydroxyethyl) - 3-methylpyrazole, 4, 5-diamino-l-ethyl-3-methylpyrazole, 4,5- diamino-l-ethyl-3- (4' -methoxyphenyl) pyrazole, 4, 5-diamino-l- ethyl-3-hydroxymethylpyrazole, 4, 5-diamino-3-hydroxymethyl-l- methylpyrazole, 4, 5-diamino-3-hydroxymethyl-l-isopropyl- pyrazole, 4, 5-diamino-3-methyl-l-isopropylpyrazole and 4- amino-5- (2' -aminoethyl) amino-1, 3-dimethylpyrazole, and the addition salts thereof.
Mention may also be made of the diaminopyrazolinones described in patent application FR 2 886 137 and in particular 2, 3-diamino-6, 7-dihydro-lH, 5H-pyrazol-l-one and salts thereof. In general, the addition salts of the additional oxidation bases and of the couplers that may be used in the context of the invention are chosen especially from the addition salts with an acid, such as the 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, ammonium hydroxide, amines or alkanolamines .
The dyeing composition in accordance with the invention may also contain one or more direct dyes which may, in particular, be chosen from nitrobenzene dyes, azo direct dyes or methine direct dyes. These direct dyes may be of nonionic, anionic or cationic nature.
The medium suitable for dyeing, also known as dyeing vehicle, generally comprises water or a mixture of water and of one or more solvents such as, for example, C1-C4 lower alkanols, for instance ethanol and isopropanol, polyols such as propylene glycol, dipropylene glycol or glycerol, and polyol ethers such as dipropylene glycol monomethyl ether.
The solvent (s) is (are) in general present in proportions which may be between 1% and 40% by weight approximately, and more preferably between 3% and 30% by weight approximately, relative to the total weight of the dyeing composition. The dyeing composition in accordance with the invention may also contain various adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof, inorganic or organic thickening agents and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetrants, sequestrants, fragrances, buffers, dispersants, conditioning agents such as, for example, volatile or non-volatile, modified or unmodified silicones, 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 relative to the weight of the composition.
Of course, a person skilled in the art will take care to choose this or these optional additional compounds so that the advantageous properties intrinsically linked to the oxidation dyeing composition according to the invention are not, or not substantially, impaired by the envisaged addition (s).
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 may be adjusted to the desired value by using acidifying or basifying agents commonly used in the dyeing of keratin fibres or else by means of conventional buffering systems.
Among the acidifying agents mention may be made, by way of example, of 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.
Among the basifying agents, mention may be made, by way of example, of aqueous ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamines and also derivatives thereof, sodium or potassium hydroxides and compounds of formula (III) below:
N W N
Rc Rd (III) in which W is a propylene residue optionally substituted with a hydroxyl group or a Ci-C4 alkyl radical; Ra, Rb, Rc and Rd, which are identical or different, represent a hydrogen atom, a Ci-C4 alkyl radical or a Ci-C4 hydroxyalkyl radical.
The composition according to the invention may comprise one or more oxidizing agents.
The oxidizing agents are those conventionally used for the oxidation dyeing of keratin fibres, which are, for example, hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulphates, peracids and oxidase enzymes, among which mention may be made of peroxidases, 2-electron oxidoreductases such as uricases and 4-electron oxygenases such as laccases. Hydrogen peroxide is particularly preferred.
The composition with or without oxidizing agent according to the invention may be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratin fibres, and especially human hair.
It may result from the mixing of several compositions at the time of use. In a first particular variant, 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 compounds of formula (I) or of formula (II) or salts thereof, and optionally one or more couplers, a second composition comprising the oxidation base(s) of formula (II) or their addition salts with an acid and optionally a third composition comprising one or more oxidizing agents as described previously, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (II) being greater than 1 in the mixture of the first two compositions.
In a second particular variant, it results from the mixing of two compositions, one comprising one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid, the oxidation base(s) of formula (II) or their addition salts with an acid, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula
(II) being greater than 1, optionally one or more additional oxidation bases other than the compounds of formula (I) or of formula (II) or salts thereof, and optionally one or more couplers, another composition comprising one or more oxidizing agents as described previously.
In a different embodiment, 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 compounds of formula (I) or of formula (III) or salts thereof, and optionally one or more couplers, a second composition comprising the oxidation base(s) of formula (III) or salts thereof optionally one or more additional oxidation bases other than the compounds of formula (I) or of formula (III) or salts thereof, and optionally one or more couplers, the molar ratio, in the mixture of the two compositions, of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (III) being greater than 0.2, and optionally a third composition comprising one or more oxidizing agents as described previously. In a second particular variant, it results from the mixing of two compositions, one comprising one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid, the oxidation base(s) of formula (III) or salts thereof, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (III) being greater than 0.2, optionally one or more additional oxidation bases other than the compounds of formula (I) or of formula (III) or salts thereof, and optionally one or more couplers, another composition comprising one or more oxidizing agents as described previously.
The composition of the invention is therefore applied to the hair for colouring keratin fibres either as is, or in the presence of one or more oxidizing agents for colouring keratin fibres .
The method of the present invention is a method in which, applied to the fibres, is the composition without oxidizing agent according to the present invention as defined previously, either alone or in the presence of one or more oxidizing agents for a sufficient time to develop the desired colouring. The colour may be developed at acid, neutral or alkaline pH and the oxidizing agent may be added to the composition of the invention only at the time of use or it may be used starting from an oxidizing composition containing it, applied simultaneously with or sequentially to the composition of the invention.
According to one particular embodiment, the composition without oxidizing agent according to the present invention is mixed, preferably at the time of use, with a composition containing, in a medium suitable for dyeing, one or more oxidizing agents. The mixture obtained is then applied to the keratin fibres. After a leave-in time of 3 to 50 minutes approximately, preferably 5 to 30 minutes approximately, the keratin fibres are rinsed, optionally washed with shampoo, rinsed again, then dried.
The oxidizing agents are those indicated previously. The oxidizing composition may also contain various additives conventionally used in compositions for dyeing hair and as defined previously.
The pH of the oxidizing composition containing the oxidizing agent is such that after mixing with the dyeing composition, the pH of the resulting composition applied to the keratin fibres preferably varies between 3 and 12 approximately, and more preferably still between 5 and 11. It may be adjusted to the desired value by means of acidifying or basifying agents customarily used in the dyeing of keratin fibres and as defined previously.
Another subject of the invention is a dyeing kit or multicompartment device in which a first compartment contains the dyeing composition without oxidizing agent of the present invention defined above comprising one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid and one or more oxidation bases chosen from the compounds of formula (II) or their addition salts with an acid, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (II) being greater than 1, and a second compartment contains one or more oxidizing agents .
A second device is constituted by a first compartment containing a composition 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 those of formula (I) or (II) or their addition salts with an acid, optionally one or more couplers and a second compartment containing a composition that comprises one or more oxidation bases chosen from the compounds of formula (II) or their addition salts with an acid and optionally one or more couplers, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (II) of the mixture of the compositions of the two compartments being greater than 1. A third device may optionally comprise the two compartments from the second device plus a third compartment containing a composition that comprises one or more oxidizing agents.
According to a different embodiment, the subject of the invention is also a dyeing kit or multicompartment device in which a first compartment contains the dyeing composition without oxidizing agent of the present invention defined above comprising one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid and one or more oxidation bases chosen from the compounds of formula (III) or their addition salts with an acid, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (III) being greater than 0.2, and a second compartment contains one or more oxidizing agents.
A second device is constituted by a first compartment containing a composition 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 those of formula (I) or (III) or their addition salts with an acid, optionally one or more couplers and a second compartment containing a composition that comprises one or more oxidation bases chosen from the compounds of formula (III) or their addition salts with an acid, optionally one or more additional oxidation bases other than those of formula (I) or (III) or their addition salts with an acid, and optionally one or more couplers, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (III) being greater than 0.2. A third device may optionally comprise the two compartments from the second device plus a third compartment containing a composition that comprises one or more oxidizing agents. These devices may be equipped with a means that makes it possible to deliver the desired mixture to the hair, such as the devices described in patent FR-2 586 913 in the name of the applicant.
The examples that follow serve to illustrate the invention without however exhibiting a limiting nature.
EXAMPLES
DYEING EXAMPLES Cl, C2 , C3
The following compositions Cl, C2 and C3 were prepared:
Figure imgf000015_0001
Figure imgf000016_0001
Figure imgf000017_0001
AM: active material
Method of application
Each composition was diluted extemporaneously with 1 times its weight of 20-volume aqueous hydrogen peroxide solution.
Each of the mixtures was applied to grey hair containing 90% white hair in an amount of 10 g of mixture per 1 g of hair. After leaving in for 30 minutes at ambient temperature, the hair was then rinsed, washed with a standard shampoo and dried.
Results
The hair colouring was evaluated visually.
Figure imgf000017_0002
DYEING EXAMPLES C4 and C5
The following compositions C4 and C5 were prepared
Figure imgf000017_0003
Figure imgf000018_0001
AM: active material
Method of application
Each composition was diluted extemporaneously with 1 times its weight of 20-volume aqueous hydrogen peroxide solution.
Each of the mixtures was applied to grey hair containing 90% white hair in an amount of 10 g of mixture per 1 g of hair. After leaving in for 30 minutes at ambient temperature, the hair was then rinsed, washed with a standard shampoo and dried. Results
The hair colouring was evaluated visually.
Figure imgf000019_0001

Claims

1. Composition for dyeing keratin fibres comprising, in a medium suitable for dyeing keratin fibres: one or more oxidation bases chosen from the compound of formula (I) or its addition salts with an acid,
Figure imgf000020_0001
and one or more oxidation bases chosen from para- phenylenediamines of formula (II) or their addition salts with an acid; para-aminophenols of formula (III) or their addition salts with an acid: :
Figure imgf000020_0002
Wherein in formula (I) Ri, which are identical or different, represent a hydrogen atom or a hydroxyethyl radical and R2 represents a hydrogen atom or a methyl radical, and wherein in formula (III) R represents a hydrogen atom or a methyl radical, the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (II) when present being greater than 1 and the molar ratio of the oxidation base(s) of formula
(I) to the oxidation base(s) of formula (III) when present being from 0.2 to 20.
2. Composition according to the preceding claim, characterized in that the content of each of the compounds of formula (I) (II) or (III) is, for each, between 0.001 and 10% by weight approximately of the total weight of the dyeing composition, preferably between 0.005 and 6%.
3. Composition according to one of the preceding claims, in which the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (II) is greater than 1 and up to 50, preferably is from 1.5 to 30.
4. Composition according to one of the preceding claims, in which the para-phenylenediamine oxidation base of formula (II) is chosen from para-phenylenediamine, para-toluenediamine, N, N-bis (β-hydroxyethyl) -para-phenylenediamine, or the corresponding addition salts with an acid.
5. Composition according to claim 1 in which the molar ratio of the oxidation base(s) of formula (I) to the oxidation base(s) of formula (III) is from 0.5 to 10.
6. Composition according to one of the preceding claims, in which the para-aminophenol (s) of formula (III) are chosen from para-aminophenol, 3-methyl-4-aminophenol or their addition salts with an acid.
7. Composition according to any one of the preceding claims, characterized in that it contains one or more couplers chosen from meta-phenylenediamines, meta-aminophenols, meta- diphenols, naphthalene couplers, heterocyclic couplers and addition salts thereof.
8. Composition according to any one of the preceding claims, characterized in that it contains one or more oxidizing agents.
9. Composition according to the preceding claim, characterized in that the oxidizing agent is chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts, peracids and oxidase enzymes, and preferably hydrogen peroxide.
10. Method for dyeing keratin fibres, in which the composition as defined in any one of Claims 1 to 9 is applied to the keratin fibres in the presence of one or more oxidizing agents for a time sufficient to develop the desired colouring.
11. Multicompartment device, in which a first compartment contains a dyeing composition as defined in any one of Claims 1 to 9 and a second compartment contains one or more oxidizing agents.
PCT/EP2010/056896 2009-05-19 2010-05-19 Dyeing composition comprising a secondary para-phenylenediamine oxidation base and a selected para-phenylenediamine or para-aminophenol oxidation base WO2010133639A1 (en)

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FR0953347A FR2945736B1 (en) 2009-05-19 2009-05-19 TINCTORIAL COMPOSITION COMPRISING A SECONDARY PARA-PHENYLENE DIAMINE OXIDATION BASE AND A SELECTED PARA-PHENYLENE DIAMINE OXIDATION BASE
FR0953348 2009-05-19
FR0953348A FR2945737B1 (en) 2009-05-19 2009-05-19 TINCTORIAL COMPOSITION COMPRISING A SECONDARY PARA-PHENYLENE DIAMINE OXIDATION BASE AND A PARTICULAR PARA-AMINO PHENOL OXIDATION BASE
FR0953347 2009-05-19
US18407909P 2009-06-04 2009-06-04
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US9012691B2 (en) 2012-10-26 2015-04-21 The Procter & Gamble Company Process for preparing primary intermediates for dyeing keratin fibers
US9309185B2 (en) 2012-10-26 2016-04-12 The Procter & Gamble Company Process for preparing primary intermediates for dyeing keratin fibers
US9539192B2 (en) 2014-04-02 2017-01-10 Noxell Corporation Hair colouring compositions, kits, method, and use thereof
US9587116B2 (en) 2014-11-04 2017-03-07 Noxell Corporation Azo direct dyes and method for dyeing hair using these dyes
US9688609B2 (en) 2014-11-04 2017-06-27 Noxell Corporation Telescoping synthesis of 2-methoxymethyl-P-phenylenediamine
US9695109B2 (en) 2014-11-04 2017-07-04 Noxell Corporation Telescoping synthesis of 2-methoxymethyl-p-phenylenediamine
US9758469B2 (en) 2014-11-04 2017-09-12 Noxell Corporation Process for the preparation of 2-substituted-1,4-benzenediamines and salts thereof

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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
US9012691B2 (en) 2012-10-26 2015-04-21 The Procter & Gamble Company Process for preparing primary intermediates for dyeing keratin fibers
US9309185B2 (en) 2012-10-26 2016-04-12 The Procter & Gamble Company Process for preparing primary intermediates for dyeing keratin fibers
US9539192B2 (en) 2014-04-02 2017-01-10 Noxell Corporation Hair colouring compositions, kits, method, and use thereof
US9587116B2 (en) 2014-11-04 2017-03-07 Noxell Corporation Azo direct dyes and method for dyeing hair using these dyes
US9688609B2 (en) 2014-11-04 2017-06-27 Noxell Corporation Telescoping synthesis of 2-methoxymethyl-P-phenylenediamine
US9695109B2 (en) 2014-11-04 2017-07-04 Noxell Corporation Telescoping synthesis of 2-methoxymethyl-p-phenylenediamine
US9758469B2 (en) 2014-11-04 2017-09-12 Noxell Corporation Process for the preparation of 2-substituted-1,4-benzenediamines and salts thereof

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