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WO2008049767A1 - Composition utilisée pour colorer par oxydation des fibres kératiniques comprenant au moins un sel d'ammonium particulier dérivé de 18mea et méthode de coloration comprenant l'utilisation de ladite composition - Google Patents

Composition utilisée pour colorer par oxydation des fibres kératiniques comprenant au moins un sel d'ammonium particulier dérivé de 18mea et méthode de coloration comprenant l'utilisation de ladite composition Download PDF

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Publication number
WO2008049767A1
WO2008049767A1 PCT/EP2007/061072 EP2007061072W WO2008049767A1 WO 2008049767 A1 WO2008049767 A1 WO 2008049767A1 EP 2007061072 W EP2007061072 W EP 2007061072W WO 2008049767 A1 WO2008049767 A1 WO 2008049767A1
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radical
alkyl
group
formula
crc
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PCT/EP2007/061072
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English (en)
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Christelle Demeulenaere
Christine Rondeau
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L'oreal
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Priority claimed from FR0654508A external-priority patent/FR2907671B1/fr
Priority claimed from FR0654511A external-priority patent/FR2907669B1/fr
Application filed by L'oreal filed Critical L'oreal
Priority to EP07821437A priority Critical patent/EP2076237A1/fr
Publication of WO2008049767A1 publication Critical patent/WO2008049767A1/fr

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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
    • A61K8/42—Amides
    • 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
    • A61K8/416—Quaternary ammonium 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
    • A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • COMPOSITION FOR OXIDATION DYEING KERATINOUS FIBRES COMPRISING AT LEAST ONE PARTICULAR AMMONIUM SALT DERIVED FROM 18MEA, AND A COLOURING METHOD USING THE COMPOSITION
  • the present invention relates to a composition for oxidation dyeing keratinous fibres, in particular human keratinous fibres such as hair, comprising, in a medium appropriate for dyeing, i) at least one oxidation base; ii) at least one coupling agent; iii) at least one particular ammonium salt; iv) at least one ceramide compound or at least one particular quaternary polyammonium compound.
  • the invention also relates to a dyeing method employing said composition, and to a multi-compartment device containing the composition.
  • oxidation bases such as ortho- or paraphenylenediamines, ortho- or paraaminophenols or heterocyclic compounds
  • oxidation bases are colourless or slightly coloured compounds which, when associated with oxidizing agents, can give rise to coloured compounds by an oxidative condensation process. Varying the shades obtained with such oxidation bases by associating them with coupling agents or colour modifiers is also known, these latter being selected from aromatic metadiamines, metaaminophenols, metadiphenols and certain heterocyclic compounds such as indole compounds.
  • the variety of molecules employed for the oxidation bases and coupling agents means that a rich palette of colours can be obtained.
  • the "permanent" colour obtained using such oxidation dyes must also satisfy a certain number of requirements. Thus, it must be harmless from a toxicological viewpoint, it must be capable of producing shades of the desired intensity and it must have good staying power when exposed to external agents such as light, poor weather, washing, permanent waves, perspiration and friction.
  • the colourants must also make it possible to cover white hair, and finally must be as non-selective as possible, i.e. they must be capable of producing as little colour difference as possible throughout the length of a keratinous fibre (uniform colour), which generally has a variable sensitivity (i.e. damage) between its end and its root.
  • the aim of the present invention is to develop dye compositions with improved cosmetic properties which can also produce strong and chromatic (luminous) shades with low selectivity and good persistence as regards chemical agents (shampoo, perming lotion, etc) or natural agents (light, perspiration, etc).
  • composition for oxidation dyeing keratinous fibres in particular human keratinous fibres such as hair, comprising, in a medium appropriate for dyeing: i) at least one oxidation base; M) at least one coupling agent; Mi) at least one ammonium salt with formula (I):
  • ⁇ R represents a CH 3 CH2-CH(R3)-CH2-(CH 2 )m- group, with R 3 representing a linear or branched, saturated or unsaturated alkyl group, and m representing an integer in the range 0 to 30 inclusive;
  • Ri and R 2 which may be identical or different, represent a group selected from i) alkyl; ii) alkenyl; iii) alkoxy; iv) alkenyloxy; and v) aryl; the alkyl or alkenyl group of groups i) to iv) possibly being interrupted by one or more heteroatoms, which may be identical or different, selected from oxygen, sulphur and N(Ra) with Ra representing a hydrogen atom or an alkyl group;
  • ⁇ X represents the following aminoalkylene group: -N(R 4 )-(CH 2 ) P -, with R 4 representing a hydrogen atom or a linear or branched alkyl group, preferably a hydrogen atom
  • ⁇ Q " represents the anionic counter-ion associated with the quaternary ammonium
  • R 4 , R 5 , R 6 and R 7j which may be identical or different, designate an alkyl or hydroxyalkyl radical containing about 1 to 4 carbon atoms;
  • ⁇ n and p are whole numbers from about 2 to 20;
  • ⁇ Q' represents an anionic counter-ion associated with the quaternary ammonium.
  • the invention also provides a method for oxidation dyeing keratinous fibres, in particular human keratinous fibres such as hair, consisting of applying to the fibres the composition of the invention in the presence of an oxidizing agent for a time sufficient to obtain the desired colour.
  • the invention also pertains to dyeing devices with a plurality of compartments, or "kits", for oxidation dyeing keratinous fibres, in particular human keratinous fibres such as hair, comprising a first compartment which comprises the composition of the invention; and a second compartment comprising at least one oxidizing agent.
  • the composition of the present invention can produce a high quality colour in the keratinous fibres as regards intensity, homogeneity, tenacity and, after colouring, also a particularly agreeable feel to the fibres, especially when dry.
  • an "alkyl radical” is a linear or branched CrCi 6 hydrocarbon radical, preferably Ci-C 4 ;
  • an "alkenyl radical” is a linear or branched C2-C16 hydrocarbon radical comprising 1 to 5 double ⁇ bonds, which may or may not be conjugated, preferably Ci-C 6 comprising one or two double bonds;
  • an "alkoxy radical” is an alkyl-oxy (alkyl-O-) radical wherein the alkyl radical is a linear or branched C r Ci 6 hydrocarbon radical, preferably CrC 6 ;
  • an "alkenyloxy radical” is an alkenyl-oxy radical wherein the alkenyl radical is a radical as defined above;
  • an "aryl" radical represents a mono- or poly-cyclic group, which may or may not be condensed, comprising 6 to 19 carbon atoms, wherein at least one cycle is aromatic; preferably, the aryl radical is a phenyl, biphenyl, naphthyl, xylyl, anthracyl, phenanthryl, indenyl or tetrahydronaphthyl radical; the aryl radical may be substituted with one or more substituents selected from a halogen atom; an alkyl group; an alkoxy group, preferably CrC 4 ; a hydroxy group: OH; a nitro group: NO2; a nitroso group: NO; a cyano group: CN; a RO-C(O)- or R-C(O)O- group with R representing a CrC 4 alkyl or hydroxy group; a carbamoyl R 2 N-C(O)-NR'- group with R, R,
  • heterocyclic radical is a non-aromatic monocyclic radical containing 5 to 6 links, comprising 1 to 3 heteroatoms selected from a nitrogen, oxygen and sulphur atom; preferably, the heterocycles are selected from pyridyl, piperazyl, morpholinylpiperidyl and pyrolidynyl groups; - a "counter-ion” is an anion or an anionic group associated with the cationic charge of the ammonium; more particularly, the anionic counter ion is selected from i) halides such as the chloride or bromide; ii) nitrates; iii) sulphonates including CrC 6 alkylsulphonat.es: AIk-S(O) 2 O " , such as methylsulphonate or ethylsulphonate; iv) arylsulphonates: Ar-S(O) 2 O " such as benzenesulphonate and
  • the composition may contain at least one oxidation base.
  • a base may be selected from those conventionally known in oxidation dyeing, and examples of those which may be cited are ortho- and para-phenylenediamines, double bases, ortho- and para- aminophenols, the following heterocyclic bases and their addition salts with an acid.
  • Ri represents a hydrogen atom, a Ci-C 4 alkyl radical, Ci-C 4 monohydroxyalkyl, C 2 -C 4 polyhydroxyalkyl, alkoxy(CrC 4 )alkyl(Ci-C 4 ), CrC 4 alkyl substituted with a nitrogen, phenyl or 4'-aminophenyl group;
  • R 2 represents a hydrogen atom, a Ci-C 4 alkyl radical, CrC 4 monohydroxyalkyl or C 2 -C 4 polyhydroxyalkyl, alkoxy(Ci-C 4 )alkyl(CrC 4 ) or CrC 4 alkyl substituted with a nitrogen group;
  • Ri and R 2 together with the nitrogen atom carrying them may also form a nitrogen- containing heterocycle with 5 or 6 links which may be substituted with one or more alkyl, hydroxy or ureido groups;
  • R 3 represents a hydrogen atom, a halogen atom such as a chlorine atom, a CrC 4 alkyl radical, sulpho, carboxy, CrC 4 monohydroxyalkyl or d-C 4 hydroxyalkoxy, CrC 4 acetylaminoalkoxy, CrC 4 mesylaminoalkoxy or CrC 4 carbamoylaminoalkoxy,
  • a halogen atom such as a chlorine atom, a CrC 4 alkyl radical, sulpho, carboxy, CrC 4 monohydroxyalkyl or d-C 4 hydroxyalkoxy, CrC 4 acetylaminoalkoxy, CrC 4 mesylaminoalkoxy or CrC 4 carbamoylaminoalkoxy
  • R 4 represents a hydrogen atom, a halogen atom or a CrC 4 alkyl radical.
  • Nitrogen-containing groups with formula (A) above which may be cited are the amino, monoalkyl(Ci-C 4 )amino, dialkyl(Ci-C 4 )amino, trialkyl(Ci-C 4 )amino, monohydroxyalkyl(Ci-C 4 )amino, imidazolinium and ammonium radicals.
  • paraphenylenediamines with formula (A) above which may be cited are paraphenylenediamine, paratoluylenediamine 1 -methyl-2,5- diaminobenzene, 2-chloro-paraphenylenediamine, 2,3-dimethyl- paraphenylenediamine, 2,6-dimethyl-paraphenylenediamine, 2,6-diethyl- paraphenylenediamine, 2,5-dimethyl-paraphenylenediamine, N,N-dimethyl- paraphenylenediamine, N,N-diethyl-paraphenylenediamine, N,N-dipropyl- paraphenylenediamine, 4-amino-N,N-diethyl-3-methyl-aniline, N,N-bis-( ⁇ - hydroxyethyl)-paraphenylenediamine, 4-N,N-bis-( ⁇ -hydroxyethyl)amino-2-methyl- aniline, Ia 4-N
  • 2-hydroxymethyl-paraphenylenediamine N,N-dimethyl-3-methyl- paraphenylenediamine, N,N-(ethyl, ⁇ -hydroxyethyl)-paraphenylenediamine, N-( ⁇ , ⁇ - dihydroxypropyl)-paraphenylenediamine, N-(4'-aminophenyl)- paraphenylenediamine, N-phenyl-paraphenylenediamine, 2- ⁇ -hydroxyethyloxy- paraphenylenediamine, 2- ⁇ -acetylaminoethyloxy-paraphenylenediamine,
  • More particularly preferred paraphenylenediamines with formula (A) above are paraphenylenediamine, paratoluylenediamine, 2-isopropyl- paraphenylenediamine, 2- ⁇ -hydroxyethyl-paraphenylenediamine,
  • soluble bases means compounds comprising at least two aromatic nuclei on which amino and/or hydroxyl groups are carried.
  • Double bases which may be used as oxidation bases in the dye compositions of the invention which may be cited are compounds with formula (B) below, and their addition salts with an acid:
  • - Zi and Z 2 which may be identical or different, represent a hydroxyl radical or -NH 2 radical which may be substituted with a CrC 4 alkyl radical or by a connecting arm Y;
  • the connecting arm Y represents a linear or branched alkylene chain containing 1 to 14 carbon atoms which may be interrupted or terminated by one or more nitrogen-containing groups and/or by one or more heteroatoms such as oxygen, sulphur or nitrogen atoms, and is optionally substituted with one or more hydroxyl radicals or C r C 6 alkoxy radicals;
  • R 5 and R 6 represent a hydrogen or halogen atom, a Ci-C 4 alkyl radical, CrC 4 monohydroxyalkyl, C 2 -C 4 polyhydroxyalkyl, CrC 4 aminoalkyl or a connecting arm Y;
  • - R 7 , Re, Rs, Rio, Rn and Ri 2 which may be identical or different, represent a hydrogen atom, a connecting arm Y or a Ci-C 4 alkyl radical; it being understood that the compounds with formula (B) comprise only a single connecting arm Y per molecule.
  • Nitrogen-containing groups with formula (B) above which may be cited include amino, monoalkyl(Ci-C 4 )amino, dialkyl(Ci-C 4 )amino, trialkyl(Ci-C 4 )amino, monohydroxyalkyl(Ci-C 4 )amino, imidazolinium and ammonium radicals.
  • double bases with formulae (B) above which may be cited include N,N'-bis-( ⁇ -hydroxyethyl)-N,N'-bis-(4'-aminophenyl)-1 ,3-diamino- propanol, 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-methyl-aminophenyl)- tetramethylenediamine, N,N'-bis-(ethyl)-N,N'-bis-(4'-amino-3'-methylphenyl)- ethylenediamine, 1 ,8-bis-(2,5-diaminophenoxy)-3,5-dioxaoctane, and their addition salts with an acid.
  • R- 13 represents a hydrogen atom, a halogen atom such as fluorine, a CrC 4 alkyl,
  • CrC 4 monohydroxyalkyl, alkoxy(Ci-C 4 )alkyl(Ci-C 4 ), CrC 4 aminoalkyl or CrC 4 hydroxyalkyl(Ci-C 4 )aminoalkyl radical.
  • Ru represents a hydrogen atom or a halogen atom such as fluorine, a CrC 4 alkyl,
  • para-aminophenols with formula (C) above which may be cited are para-aminophenol, 4-amino-3-methyl-phenol, 4-amino-3-fluoro-phenol, 4-amino-3-hydroxymethyl-phenol, 4-amino-2-methyl-phenol, 4-amino-2- hydroxymethyl-phenol, 4-amino-2-methoxymethyl-phenol, 4-amino-2- aminomethyl-phenol, 4-amino-2-( ⁇ -hydroxyethyl-aminomethyl)-phenol, and their addition salts with an acid;
  • ortho-aminophenols which may be used as oxidation bases in the context of the present invention are selected from 2-amino-phenol, 2-amino-1 - hydroxy-5-methyl-benzene, 2-amino-1 -hydroxy-6-methyl-benzene, 5-acetamido-2- amino-phenol, and their addition salts with an acid;
  • heterocyclic bases which may be used as oxidation bases in the dye compositions of the invention which may be cited are pyridine derivatives, pyrimidine derivatives, pyrazole derivatives and their addition salts with an acid.
  • pyridine derivatives which may be cited are the compounds described, for example, in British patents GB 1 026 978 and GB 1 153 196, such as 2,5-diamino-pyridine, 2-(4-methoxyphenyl)amino-3-amino-pyridine, 2,3-diamino-6-methoxy-pyridine, 2-( ⁇ -methoxyethyl)amino-3-amino-6-methoxy pyridine, 3,4-diamino-pyridine and their addition salts with an acid.
  • pyrimidine derivatives which may be cited are the compounds described, for example, in German patent DE 2 359 399 or Japanese patents JP 88-169 571 and JP 91 -10659 or International patent application WO 96/15765, such as 2,4,5, 6-tetra-aminopyrimidine, 4-hydroxy-2,5,6- triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6- diaminopyrimidine, 2,5,6-triaminopyrimidine, and pyrazolo-pyrimidine derivatives such as those mentioned in French patent application FR-A-2 750 048.
  • Examples of these which may be cited include pyrazolo-[1 ,5-a]-pyrimidine-3,7-diamine; 2,5- dimethyl-pyrazolo-[1 ,5-a]-pyrimidine-3,7-diamine; pyrazolo-[1 ,5-a]-pyrimidine-3,5- diamine; 2,7-dimethyl-pyrazolo-[1 ,5-a]-pyrimidine-3,5-diamine; 3-amino-pyrazolo- [1 ,5-a]-pyrimidin-7-ol; 3-amino-pyrazolo-[1 ,5-a]-pyrimidin-5-ol; 2-(3-amino pyrazolo-[1 ,5-a]-pyrimidin-7-ylamino)-ethanol; 2-(7-amino-pyrazolo-[1 ,5-a]- pyrimidin-3-ylamino)-ethanol; 2-[(3-a
  • pyrazole derivatives which may be cited are the compounds described in DE 3 843 892, 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-1 -methyl-pyrazole, 3,4-diamino-pyrazole, 4,5-diamino-
  • 1-(4'-chlorobenzyl)-pyrazole 4,5-diamino 1 ,3-dimethyl-pyrazole, 4,5-diamino-3- methyl-1 -phenyl-pyrazole, 4,5-diamino 1-methyl-3-phenyl-pyrazole, 4-amino-1 ,3- dimethyl-5-hydrazino-pyrazole, 1 -benzyl-4,5-diamino-3-methyl-pyrazole, 4,5- diamino-3-tert-butyl-1 -methyl-pyrazole, 4,5-diamino-1 -tert-butyl-3-methyl-pyrazole, 4,5-diamino-1 -( ⁇ -hydroxyethyl)-3-methyl pyrazole, 4,5-diamino-1 -( ⁇ -hydroxyethyl)- pyrazole, 4,5-diamino-1 -ethyl-3-methyl-pyrazole, 4,5-d
  • the oxidation bases preferably represent 0.0001 % to 20% by weight of the total composition weight, more preferably 0.005% to 10% by weight of that weight.
  • the coupling agents which may be used in the composition with the oxidation base of the invention are those which are conventionally used in oxidation dye compositions, i.e. meta-aminophenols, meta-phenylenediamines, meta-diphenols, naphthols and heterocyclic coupling agents such as, for example indole derivatives, indoline derivatives, sesamol and its derivatives, pyridine derivatives, pyrazolotriazole derivatives, pyrazolones, indazoles, benzimidazoles, benzothiazoles, benzoxazoles, 1 ,3-benzodioxoles, quinolines and their addition salts with an acid.
  • meta-aminophenols i.e. meta-aminophenols, meta-phenylenediamines, meta-diphenols, naphthols and heterocyclic coupling agents
  • indole derivatives indoline derivatives, sesamol and its derivatives
  • these coupling agents are selected from 1 -( ⁇ -hydroxyethyloxy)-2,4-diaminobenzene, 2-methyl-5-amino-phenol, 5-N-( ⁇ - hydroxyethyl)amino-2-methyl-phenol, 3-aminophenol or 1 -hydroxy-3-a mi no- benzene, 1 ,3-dihydroxybenzene, 1 ,3-dihydroxy-2-methyl-benzene, 4-chloro- 1 ,3-dihydroxy-benzene, 2-amino 4-( ⁇ -hydroxyethylamino)-1 -methoxy-benzene, 1 ,3-diaminobenzene, 1 ,3-bis-(2,4-diaminophenoxy)-propane, sesamol, 1 -amino-2- methoxy-4,5-methylenedioxy benzene, I' ⁇ -naphthol, 6-hydroxy-indole, 4-hydroxy- indole, 4-
  • These coupling agents preferably represent about 0.0001 % to 20% by weight of the total composition weight, more preferably about 0.005% to 10% by weight.
  • addition salts with an acid of the oxidation bases and coupling agents are selected from hydrochlorides, hydrobromides, sulphates, tartrates, lactates and acetates.
  • composition of the invention also contains at least one ammonium salt with formula (I) as defined above.
  • the ammonium salt with formula (I) includes a group R representing an alkyl group containing 8 to 40 carbon atoms, m being an integer between 3 and 25 inclusive, advantageously between 10 and 20.
  • the ammonium salt with formula (I) contains a group R 3 which represents an alkyl group comprising less than 12 carbon atoms, particularly 1 to 6 carbon atoms; as an example, R 3 represents a methyl group and Ri and R 2 particularly represent an alkyl or alkoxy group containing 1 to 8 carbon atoms, such as: ethoxy, polyethoxy, propoxy, polypropoxy or methyl.
  • ammonium salt with formula (I) containing a group Y representing an alkoxy group such as: ethoxy, polyethoxy, propoxy, polypropoxy, or alkyl containing 1 to 6 carbon atoms.
  • Y represents an ethyl group.
  • Q " represents the anionic counter-ion of the ammonium salt with formula (I), which may be selected from halides, alkyl sulphates such as methyl sulphate and ethyl sulphate; alkoxysulphates such as methoxysulphate and ethoxysulphate; phosphates; lactate; citrate; acetate and tartrate.
  • ammonium salt of formula (I) is not derived from linolic acid especially anteiso linolinic acid.
  • the ammonium salt with formula (I) is 18MEA in the quaternized form, which comprises a group R deriving from 18- methyl eicosanoic acid, i.e. R 3 is a methyl and m is 16.
  • 18MEA in the quaternized form means a quaternary ammonium salt derived from the fatty acid methyl eicosanoic acid (Methyl Eicosanoic Acid - 18MEA). Such a 18MEA compound in the quaternized form is sold by CRODA
  • 18MEA in the quaternized form corresponds to quaternized eicosanoic acid derivatives of Ci 0 -C 40 lsoalkylamidopropylethyldimonium methosulphate: R-C(O)-NH-(CH 2 ) 3 -N + (Me) 2 Et, CH 3 CH 2 -OSO 3 " , with R representing the following alkyl group: CH 3 CH 2 -CH(CH 3 )- CH 2 -(CH 2 )I 6 -.
  • ammonium salt with formula (I) above is present in the composition of the invention in a quantity in the range 0.001 % to 2% by weight with respect to the composition weight, in particular in the range 0.01 % to 1 %.
  • the ammonium salt is present in the composition in a quantity in the range 0.02% to 0.4%.
  • composition of the invention also contains a) either a compound of the ceramide type or b) a quaternary polyammonium polymer with formula (II): a) Either the composition of the invention also contains at least one ceramide type compound.
  • Ceramides or their analogues are known to protect and/or repair skin and/or hair fibres from attack by the various agents and treatments cited above. In particular, they have a barrier effect which limits protein loss, and they also reinforce cuticular cohesion.
  • international patent application WO 00/44345 describes a means for improving cosmetic properties such as untangling the hair by applying a composition comprising a ceramide type compound such as N- oleoyldihydrosphingosine in association with a hydrogenated sunflower wax and behenyl trimethyl ammonium chloride in water.
  • ceramide type compound means natural or synthetic ceramides and/or glycoceramides and/or pseudoceramides and/or neoceramides, with formula (I) below.
  • Ceramide type compounds have, for example, been described in patent applications DE4424530, DE4424533, DE4402929, DE4420736,
  • Ceramide type compounds which may be used in the present invention have the following general formula (XX):
  • R-J4 designates: i) a linear or branched, saturated or unsaturated hydrocarbon radical C1-C50, preferably C 5 -C 5 O, said radical possibly being substituted with one or more hydroxy groups which may be esterified by an acid R 19 COOH, with Rig being a linear or branched, saturated or unsaturated Ci-C3 5 hydrocarbon radical, which may be mono- or polyhydroxylated, the hydroxy group or groups of radical R19 possibly being esterified by a linear or branched, saturated or unsaturated Ci-C 35 fatty acid, which may be mono- or polyhydroxylated; ii) a R"-(NR-CO) q -R' radical, with R designating a hydrogen atom or a mono- or polyhydroxylated, preferably mono-hydroxylated C r C 2 o hydrocarbon radical, R' and R" are hydrocarbon radicals wherein the sum of the carbon atoms is in the range 9 to 30, R' being a di
  • ⁇ R- 15 is selected from a hydrogen atom, a saccharide type radical, in particular a (glycosyl) n , (galactosyl) m or sulphogalactosyl radical, a sulphate or phosphate residue, a phosphorylethylamine radical and a phosphorylethylammonium radical, in which n is an integer in the range 1 to 4 inclusive, and m is an integer in the range 1 to 8 inclusive;
  • ⁇ R-16 designates a saturated or unsaturated, hydroxylated or non- hydroxylated CrC 33 hydrocarbon radical, the hydroxy group or groups possibly being esterified by a mineral acid or an acid Ri 9 COOH, Ri 9 having the meanings given above, the hydroxyl group or groups possibly being etherified by a (glycosyl) n , (galactosyl) mj sulphogalactosyl, phosphorylethylamine or phosphorylethylammonium radical, Ri ⁇ possibly being substituted with one or more Ci-Ci 4 alkyl radicals; preferably, Ri 6 designates a Ci 5 -C 26 ⁇ -hydroxyalkyl radical, the hydroxyl group optionally being esterified by a Ci 6 -C 30 ⁇ - hydroxyacid;
  • R-J7 designates a hydrogen atom, a saturated or unsaturated, linear or branched non-alkoxylated C 3 -Cs 0 hydrocarbon radical, optionally hydroxylated such as a methyl, ethyl or a R 2 I-O-CO-(CH 2 ) radical, Rs designates a CrC 2 O hydrocarbon radical, p is an integer from 1 to 12; in particular, Ri 7 represents a Ci 0 -C 20 alkyl group;
  • R-J8 designates a hydrogen atom or a saturated or unsaturated, linear or branched CrC 30 hydrocarbon radical, which may be mono- or polyhydroxylated, the hydroxy group or groups possibly being etherified by (glycosyl) n , (galactosyl) mj sulphogalactosyl, phosphorylethylamine or phosphorylethylammonium, radical; in particular, R ⁇ s represents a hydrogen atom.
  • Preferred compounds with formula (XX) include ceramides and/or glycoceramides the structures of which have been described by DOWNING in the Journal of Lipid Research Vol. 35, 2060-2068, 1994, or those described in French patent FR-2 673 179, the teachings of which are included herewith by reference.
  • ceramide type compounds in accordance with the invention are compounds with formula (XX) wherein Ri 4 designates an alkyl or alkenyl derivative of Ci 4 -C 22 fatty acids which may be hydroxylated; in particular, Ri 4 represents a Ci 2 -C 2O alkenyl chain comprising one or more ⁇ double bonds, preferably one; Ri 5 designates a hydrogen atom; and Ri 6 designates a linear Cn- Ci7 radical which may be hydroxylated and preferably Ci 3 -Ci 5 ; more particularly, Ri6 represents an alkyl group such as methyl or ethyl hydroxylated by one or more hydroxy groups, preferably one hydroxy group.
  • Examples of such compounds are: - 2-N-linoleoylamino-octadecane-1 ,3-diol;
  • Ri 4 designates a saturated or unsaturated alkyl radical derived from Ci 2 -C 22 fatty acids
  • Ri 5 designates a galactosyl or sulphogalactosyl radical
  • An example which may be cited is the product constituted by a mixture of glycoceramides, sold under the trade name GLYCOCER by WAITAKI INTERNATIONAL BIOSCIENCES.
  • QUESTAMIDE H bis-(N- hydroxyethyl N-cetyl) malonamide sold by QUEST.
  • the concentration of ceramide type compounds may be in the range about 0.0001 % to 20% by weight with respect to the total composition weight, preferably in the range about 0.001 % to 10% and more preferably in the range 0.01 % to 3% by weight; r the composition of the invention also contains at least one quaternary polyammonium with formula (II) as defined above, preferably those comprising groups R 4 , R 5 , Re and R 7 independently representing a methyl or ethyl radical and Q " representing the anionic counter-ion of the polyammonium which may be selected from the halide, sulphate, sulphite, sulphides, nitrate, acetate, borate, citrate, tartrate, bisulphate, bisulphite, sulphate, phosphate, more preferably the halide ion such as the chloride, bromide
  • Said quaternary polyammonium compounds with formula (II) are prepared and described in French patent FR-A-2 270 846.
  • a particular embodiment of the invention concerns ionene quaternary polyammonium compounds such as Hexadimethrine Chloride corresponding to a polymer of N, N, N', N'- tetramethylhexamethylenediamine and 1 ,3-dichloropropylene.
  • the composition of the invention may also contain dialkyldiallylammonium cyclohomopolymers comprising, as the principal constituent of the chain, motifs with the following structure (III):
  • ⁇ Ri independently of each other, designates a hydrogen atom or a methyl radical
  • ⁇ R 2 and R 3 independently of each other, designate an alkyl group containing 1 to 6 carbon atoms, a hydroxyalkyl group in which the alkyl group preferably contains 1 to 5 carbon atoms, a lower amidoalkyl group (Ci-C 4 ), or R 2 and R 3 may, jointly with the nitrogen atom to which they are attached, designate heterocyclic groups such as piperidinyl or morpholinyl; R 2 and R 3 independently of each other preferably designate an alkyl group containing 1 to 4 carbon atoms; ⁇ Q" " represents an anionic counter ion associated with the quaternary ammonium, and may be selected from halides such as the bromide or chloride; acetate; alkyl sulphates such as methyl sulphate and ethyl sulphate; alkoxysulphates such as methoxysulphate and ethoxysulphate; citrate; tartrate and phosphates.
  • These polymers have in particular
  • Preferred polymers as defined above are those with formula (III) wherein R 1 designates hydrogen, and R 2 and R 3 designate a methyl radical.
  • R 1 designates hydrogen
  • R 2 and R 3 designate a methyl radical.
  • a particular compound of this latter genre which may be cited is the dimethyldiallylammonium chloride homopolymer sold under the trade name "Merquat 100" by Calgon (and its low mass average molecular mass homologues).
  • the quantity by weight of the dialkyldiallylammonium cyclohomopolymer with formula (III) is preferably in the range about 0.05% to 5%, more preferably in the range 0.1 % to 3%.
  • the quantity by weight of quaternary polyammonium compounds with motifs with formula (II) is preferably in the range from about 0.05% to 10%, more preferably in the range 0.2% to 5% with respect to the total composition weight.
  • composition of the invention may also contain one or more direct dyes.
  • Said direct dyes may in particular be selected from neutral, cationic or anionic dyes.
  • neutral direct dye means any direct dye which does not have in its molecular structure a quaternized nitrogen atom or COOR or SO3R substituents, where R designates a hydrogen atom, or a cation deriving from a metal or an amine, or an ammonium ion.
  • neutral direct dyes which may be cited are benzene direct dyes such as:
  • Neutral azo dyes which may be cited are Disperse Orange 3, Disperse Red 17, Disperse Black 9 and HC Yellow 7.
  • Neutral quinone dyes which may be cited are Disperse Violet 4, Disperse Blue 1 , Disperse Violet 1 , Disperse Blue 3, Disperse Blue 7, Natural Orange 6 and HC Blue 14.
  • Cationic direct dyes which may be used in the invention have at least one quaternized atom in their structure constituting at least one permanent cationic charge. This charge may be endocyclic or exocyclic.
  • endocyclic charge means that the charge is present on a heteroatom included in a cycle.
  • preferred direct dyes of the invention which may be mentioned are cationic direct dyes which have an endocyclic charge.
  • Cationic direct dyes with an exocyclic charge which may be cited are the dyes Basic Red 76, Basic Yellow 57, Basic Brown 16, Basic Brown 17, Basic Blue 99 and Basic Blue 22.
  • Endocyclic cationic direct dyes which may be cited are azo, methine or azomethine direct dyes with a quantitative ammonium group included in a cycle: i) the following colourants described in patent application EP 1 025 834 with formula (IV):
  • G represents a group selected from the following structures d to G3:
  • R2 4 designates a Ci-C 4 alkyl radical, a phenyl radical which may be substituted with a Ci-C 4 alkyl radical or a halogen atom selected from chlorine, bromine, iodine and fluorine;
  • R25 designates a Ci-C 4 alkyl radical or a phenyl radical
  • R26 and R27 which may be identical or different, represent a Ci-C 4 alkyl radical, a phenyl radical or together in Gi form a benzene ring substituted with one or more CrC 4 alkyl radicals, C r C 4 alkoxy radicals or NO 2 radicals, or together in G 2 form a benzene ring which may be substituted with one or more CrC 4 alkyl, Ci-C 4 alkoxy or NO 2 radicals;
  • R 26 may also designate a hydrogen atom
  • > Z designates an oxygen or sulphur atom or an -NR 25 group
  • > M represents a -CH, -CR (R designating d-C 4 alkyl), or -NR 28 (X " )r group;
  • K represents a -CH, -CR (R designating Ci-C 4 alkyl),or -NR 28 (X " )r group;
  • P represents a -CH, -CR (R designating Ci-C 4 alkyl), or -NR 28 (X " )r group;
  • > r designates zero or 1 ;
  • R 28 represents an O ⁇ atom, a CrC 4 alkoxy radical or a CrC 4 alkyl radical;
  • R 2 9 and R30 which may be identical or different, represent a hydrogen or halogen atom selected from chlorine, bromine, iodine and fluorine, a CrC 4 alkyl radical, a CrC 4 alkoxy radical or a -NO 2 radical;
  • X ⁇ represents an anion, preferably selected from chlorine, iodine, methyl sulphate, ethyl sulphate, acetate and perchlorate;
  • J represents: a) a group with the following structure J-i:
  • R 31 represents a hydrogen atom, a halogen atom selected from chlorine, bromine, iodine and fluorine, a CrC 4 alkyl radical, a CrC 4 alkoxy, a -OH, - NO 2 , -NHR 34 , -NR35R36, CrC 4 -NHCOalkyl radical, or with R 32 forms a cycle with 5 or 6 links which may or may not contain several heteroatoms selected from nitrogen, oxygen and sulphur;
  • R 32 represents a hydrogen atom, a halogen atom selected from chlorine, bromine, iodine and fluorine, a CrC 4 alkyl radical, a CrC 4 alkoxy radical, > or with R 33 or R 34 forms a cycle with 5 or 6 links which may or may not contain one or more heteroatoms selected from nitrogen, oxygen and sulphur;
  • R 33 represents a hydrogen atom, a -OH radical, a -NHR 34 radical, or an - NR 35 R36 radical;
  • R 34 represents a hydrogen atom, a C r C 4 alkyl radical, a C r C 4 monohydroxyalkyl radical, C 2 -C 4 poly hydroxyalkyl or a phenyl radical;
  • a heterocyclic nitrogen-containing group with 5 or 6 links which is capable of including other heteroatoms and/or carbonyl groups and which may be substituted with one or more CrC 4 alkyl, amino or phenyl radicals; and in particular a group with the following structure J 2 : in wh ich ,
  • R37 and R38 which may be identical or different, represent a hydrogen atom, a C 13 -C 10 alkyl radical, a phenyl radical;
  • n 0 or 1 , with, when n designates 1 , U designating the radical -CO-;
  • R 12 represents a hydrogen atom or a CrC 4 alkyl radical
  • Ri3 represents a hydrogen atom, an alkyl radical which may be substituted with a radical -CN or with an amino group, a 4'-aminophenyl radical or with Ri 2 forms a heterocycle which may contain oxygen and/or nitrogen which may be substituted with a C r C 4 alkyl radical;
  • Ri 4 and R 15 which may be identical or different, represent a hydrogen atom, a halogen atom such as bromine, chlorine, iodine or fluorine, a CrC 4 alkyl radical or CrC 4 alkoxy radical or a -CN radical;
  • X " represents an anion, preferably selected from the chloride, methyl sulphate and acetate
  • B represents a group selected from the following structures Bi to B 6 :
  • R 16 represents a CrC 4 alkyl radical
  • Ri7 and Ris which may be identical or different, represent a hydrogen atom or a CrC 4 alkyl radical
  • Rig represents a hydrogen atom, a CrC 4 alkoxy radical, a halogen atom such as bromine, chlorine, iodine or fluorine or an amino radical,
  • R 2O represents a hydrogen atom, a CrC 4 alkyl radical or with a carbon atom of the benzene ring forms a heterocycle which may optionally contain oxygen and/or be substituted with one or more CrC 4 alkyl groups;
  • R21 represents a hydrogen atom or a halogen atom such as bromine, chlorine, iodine or fluorine;
  • R22 and R23 which may be identical or different, represent a hydrogen atom or a C r C 4 alkyl radical
  • D 2 which may be identical or different, represent a nitrogen atom or the -CH group
  • X " represents an anion, preferably selected from the chloride, methyl sulphate and acetate
  • E represents a group selected from the following structures Ei to E 8 :
  • R' represents a CrC 4 alkyl radical
  • E may also designate a group with the following structure E 9 : in which R' represents a CrC 4 alkyl radical,
  • R 7 and Rs which may be identical or different, represent a hydrogen atom; a Ci-C 4 alkyl radical which may be substituted with a -CN, -OH or
  • -NH 2 radical or together with a carbon atom of the benzene cycle form a heterocycle which may contain oxygen or nitrogen, which may be substituted with one or more Ci-C 4 alkyl radicals; or a 4'-aminophenyl radical; > Rg and R'g, which may be identical or different, represent a hydrogen atom or halogen atom selected from chlorine, bromine, iodine and fluorine, a cyano radical, a CrC 4 alkyl radical, a CrC 4 alkoxy radical, or an acetyloxy radical;
  • X " represents an anion, preferably selected from the chloride, methyl sulphate and acetate,
  • A represents a group selected from the following structures Ai to Ai 9 :
  • R 10 which may be identical or different, represent a CrC 4 alkyl radical which may be substituted with a hydroxyl radical and Rn represents a CrC 4 alkoxy radical;
  • Ri and R 2 independently of each other represent a hydrogen atom, a CrC 4 alkyl group or may together with the 2 nitrogen atoms to which they are attached or with Z and Z 2 form a cycle with 5, 6 or 7 links;
  • > X represents the residue of a link forming a bridge;
  • n represents the integer 2, 3 or 4;
  • > KK represents a coupling agent residue
  • > R 3 and R 4 independently represent a hydrogen atom or a CrC 4 alkyl group
  • R 5 and R 6 independently represent a hydrogen atom, a C r C 4 alkyl group or a CrC 4 alkoxy group;
  • An " represents an anionic counter ion, particularly colourless; as well as the cationic dyes described in patent applications WO 95/01 772, WO 95/15 144, EP 714 954, EP 1 170 000 EP 1 166 753, EP 1 166 754 and EP 1 170 001 , which differ from the above dyes.
  • the passage of these applications devoted to cationic dyes is hereby incorporated into the present application.
  • - cationic dyes with xanthene cycles such as Basic Red 1 , Basic Red 3, Basic Red 4, Basic Violet 10 or Basic Violet 11 ;
  • - cationic dyes with phenothiazine cycles such as Basic Blue 9
  • - cationic dyes with triazole cycles such as Basic Red 22 or Basic Red 46
  • - cationic dyes with indolenine cycles such as Basic Red 14, Basic Yellow 13 , Basic Yellow 28 or Basic Yellow 29
  • - cationic dyes with phenoxazine cycles such as Basic Blue 6.
  • Anionic or acid direct dyes which may be used in the invention have in their structure at least one CO2R or SO3R group, in which R designates a hydrogen atom or a cation deriving from a metal or an amine, or an ammonium ion.
  • the anionic dyes may be selected from acid direct nitro dyes, acid azo dyes, acid azine dyes, acid triaryl methane dyes, acid indoamine dyes, acid anthraquinone dyes, indigoids and natural acid dyes.
  • Acid dyes in accordance with the invention which may be cited are colourants with the following formulae (XII), (XII'), (XIII), (XIII'), (XIV), (XIV), (XV),
  • R 7 , Re, R9, R10, R'7, R' ⁇ , R'9 and R'i 0 which may be identical or different, represent a hydrogen atom or a group selected from:
  • X, X' and X which may be identical or different, represent an oxygen atom, a sulphur atom or NR with R representing a hydrogen atom or an alkyl group;
  • R" representing a hydrogen atom, an alkyl group, an aryl, (di)(alkyl)amino or aryl(alkyl)amino group; preferably a phenylamino or phenyl group; - R"'-S(O)2-X'- with R'" representing an alkyl group, an aryl group which may optionally be substituted, and X' is as defined above;
  • - aryl(alkyl)amino optionally substituted with one or more groups selected from i) nitro; ii) nitroso; iii) (O)2S(O ⁇ )-, M + and iv) alkoxy with M + as defined above; - heteroaryl optionally substituted; preferably a benzothiazolyl group;
  • Ar-N N- with Ar representing an aryl group, optionally substituted; preferably a phenyl group optionally substituted with one or more alkyl groups, (O)2S(O ⁇ )-, M + or phenylamino;
  • R 7 with R 8 or R 8 with R 9 or R 9 with Ri 0 together form a fused benzo A' group
  • R' 7 with R' 8 or R' 8 with R' 9 or R' 9 with R'io together form a fused benzo B' group
  • ⁇ W represents a sigma bond ⁇ , an oxygen atom, a sulphur atom or a divalent radical i) -NR- with R as defined above, or ii) methylene -
  • R 3 and R b which may be identical or different, representing a hydrogen atom or an aryl group, or R 3 and R b together with the carbon atom carrying them form a spiro cycloalkyl; preferably, W represents a sulphur atom or R 3 and Rb together form a cyclohexyl group; it being understood that formulae (XII) and (XM') include at least one sulphonate (O) 2 S(O " )-, M + radical or a carboxylate (O)CO " -, M + radical on one of cycles A, A', B, B' or C; preferably sodium sulphonate;
  • dyes with formula (XII) which may be cited are: Acid Red 1 , Acid Red 4, Acid Red 13, Acid Red 14, Acid Red 18, Acid Red 27, Acid Red 32, Acid Red
  • Acid Red 35 Acid Red 37, Acid Red 40, Acid Red 41 , Acid Red 42, Acid Red
  • Acid Blue 19 Acid Orange 20, Acid Orange 24, Acid Yellow 9, Acid Yellow 36, Acid Yellow 199, Food Yellow 3; Acid Violet 7, Acid Violet 14, Acid Blue 113, Acid Blue 117,
  • Acid Black 1 Acid Brown 4, Acid Brown 20, Acid Black 26, Acid Black 52, Food
  • R-M, R-I2 and Ri 3 which may be identical or different, represent a hydrogen atom, a halogen atom, an alkyl group or -(O) 2 S(O ⁇ ), M + with M + as defined above;
  • ⁇ Ru represents a hydrogen atom, an alkyl group or a -C(O)O " , M + group with M + as defined above;
  • ⁇ R-15 represents a hydrogen atom
  • R- 16 represents an oxo, group in which case R'i 6 is absent, or R 15 with R 16 together form a double bond
  • R 17 and R 18 which may be identical or different, represent a hydrogen atom or a group selected from:
  • Ar representing an aryl group which may be substituted; preferably a phenyl group which may be substituted with one or more alkyl groups; ⁇ R 19 and R 2 o, together form either a double bond or a benzo D' group, which may be substituted;
  • ⁇ R' 16 , R'-i9 and R' 2 o which may be identical or different, represent a hydrogen atom or an alkyl group or a hydroxy group;
  • ⁇ R 2 i represents a hydrogen atom, an alkyl group, or an alkoxy group;
  • Ra and R a which may be identical or different, are as defined above; preferably, R 3 represents a hydrogen atom and R b represents an aryl group;
  • ⁇ Y represents either a hydroxy group or an oxo group
  • ⁇ represents a single bond when Y is an oxo group
  • ⁇ represents a double bond when Y represents a hydroxy group
  • formulae (XIII) and (XIM') comprise at least one sulphonate (O) 2 S(O " )-, M + radical or a carboxylate -C(O)O " , M + radical on one of cycles D or E; preferably sodium sulphonate;
  • dyes with formula (XIII) which may be cited are: Acid Red 195, Acid Yellow 23, Acid Yellow 27, Acid Yellow 76, and an example of a dye with formula (XIM') which may be cited is: Acid Yellow 17;
  • R22, R23, R24, R25, R26 and R27 which may be identical or different, represent a hydrogen atom, a halogen atom or a group selected from:
  • aryl(alkyl)amino optionally substituted, preferably substituted with one or more groups selected from alkyl and (O)2S(O ⁇ )-, M + with M + as defined above;
  • ⁇ Z' represents a hydrogen atom or a NR28R29 group with R 2 e and R29, which may be identical or different, representing a hydrogen atom or a group selected from:
  • - polyhydroxyalkyl such as hydroxyethyl; - aryl, optionally substituted with one or more groups, particularly i) alkyl such as methyl, n-dodecyl, n-butyl; ii) (O) 2 S(O " )-, M + with M + as defined above; iii) R°-C(X)-X'-, R°-X'-C(X)-, R°-X'-C(X)-X"- with R°, X, X' and X" as defined above; preferably, R° represents an alkyl group;
  • ⁇ Z represents a group selected from hydroxy and NR'28R'29 with R' 28 and
  • R'29 which may be identical or different, representing the same atoms or groups as R28 and R29 as defined above; it being understood that formulae (XIV) and (XIV) include at least one sulphonate (O) 2 S(O " )-, M + radical or a carboxylate -C(O)O " , M + radical; preferably sodium sulphonate;
  • Examples of colourants with formula (XIV) which may be cited are: Acid Blue 25, Acid Blue 43, Acid Blue 62, Acid Blue 78, Acid Blue 129, Acid Blue 138, Acid Blue 140, Acid Blue 251 , Acid Green 25, Acid Green 41 , Acid Violet 42, Acid Violet 43, Mordant Red 3; and an example of a colourant with formula (XIV) which may be cited is: Acid Black 48; d) nitro colourants with formulae (XV) and (XV):
  • R 30 , R 31 and R 32 which may be identical or different, represent a hydrogen atom, a halogen atom or a group selected from
  • alkoxy optionally substituted with one or more hydroxy groups, alkylthio optionally substituted with one or more hydroxy groups;
  • R 30 , R31 and R32 represent a hydrogen atom
  • Rc and Rd which may be identical or different, represent a hydrogen atom or an alkyl group
  • ⁇ W is as defined above; in particular, W represents a -NH- group; ⁇ ALK represents a linear or branched divalent C I -C ⁇ alkylene group; in particular, ALK represents a -CH 2 -CH 2 - group;
  • ⁇ n 1 or 2;
  • ⁇ p represents an integer in the range 1 to 5 inclusive
  • ⁇ q and t represent an integer in the range 1 to 4 inclusive
  • ⁇ u is 0 or 1 ;
  • J represents a nitro or nitroso group, in particular nitro
  • J represents an oxygen atom, a sulphur atom or a divalent -S(O) m - radical with m representing the integer 1 or 2; preferably, J represents a -SO 2 - radical;
  • ⁇ present or absent, represents a benzo group which may be substituted with one or more groups R30 as defined above;
  • formulae (XV) and (XV) include at least one sulphonate (O) 2 S(O " )-, M + radical or a carboxylate -C(O)O " , M + radical; preferably sodium sulphonate;
  • dyes with formula (XV) which may be cited are: Acid Brown 13; Acid Orange 3; examples of dyes with formula (XV) which may be cited are: Acid Yellow 1 , the sodium salt of 2,4-dinitro-1 -naphthol-7-sulphonic acid, 2-piperidino 5-nitro benzene sulphonic acid, 2(4'-N,N(2"-hydroxyethyl)amino-2'-nitro)aniline ethane sulphonic acid, 4- ⁇ -hydroxyethylamino-3-nitrobenzene sulphonic acid;
  • R33, R34, R35 and R 3 6 which may be identical or different, represent a hydrogen atom or a group selected from alkyl, aryl, which may be substituted and arylalkyl which may be substituted; in particular, an alkyl and benzyl group optionally substituted with a (O) m S(O>, M + group with M + and m as defined above;
  • R37, R38, R39, R40, R41, R42, R43 and R44 which may be identical or different, represent a hydrogen atom or a group selected from:
  • R 4 i with R 42 or R 42 with R 43 or R 43 with R 44 together form a fused benzo group: I'; with I' optionally substituted with one or more groups selected from i) nitro; ii) nitroso; iii) (O)2S(O ⁇ )-, M + ' iv) hydroxy; v) mercapto; vi) (di)(alkyl)amino; vii) R°-C(X)-X'-; viii) R°-X'- C(X)-; ix) R°-X'-C(X)-X"-; with M + , R°, X, X', X" as defined above; in particular R 37 to R 40 represent a hydrogen atom, and R 4 i to R 44 , which may be identical or different, represent a hydroxyl group or (O) 2 S
  • At least one of cycles G, H, I or I' includes at least one sulphonate (O) 2 S(O " )- radical or a carboxylate -C(O)O " radical; preferably sulphonate;
  • dyes with formula (XVI) which may be cited are: Acid Blue 1 ; Acid Blue 3; Acid Blue 7, Acid Blue 9; Acid Violet 49; Acid Green 50;
  • R45, R46, R47 and R 4 8 which may be identical or different, represent a hydrogen atom or a halogen atom
  • R49, R50, R51 and R 52 which may be identical or different, represent a hydrogen atom, a halogen atom or a group selected from:
  • R 53 R 54 , R 55 and R 4 s represent a hydrogen atom or a halogen atom;
  • G represents an oxygen atom, a sulphur atom or a NR e group with R e as defined above; in particular, G represents an oxygen atom;
  • ⁇ L represent an alcoholate O " , M + ; a thioalcoholate S “ , M + or a NR f group with R f representing a hydrogen atom or an alkyl group and M + as defined above; in particular, M + is sodium or potassium; ⁇ L' represents an oxygen atom, a sulphur atom or an ammonium group:
  • R f R 9 N + R f R 9 , with R f and R 9, which may be identical or different, representing a hydrogen atom, an alkyl group, an optionally substituted aryl group; in particular, L' represents an oxygen atom or a phenylamino group optionally substituted with one or more alkyl groups or (O) m S(O ⁇ )-, M + with m and M + as defined above;
  • Q and Q' which may be identical or different, represent an oxygen atom or a sulphur atom; in particular, Q and Q' represent an oxygen atom;
  • colourants with formula (XVII) which may be cited are: Acid Yellow 73; Acid Red 51 ; Acid Red 87; Acid Red 92; Acid Red 95 and Acid Violet 9; f) dyes derived from indole with formula (XVIII):
  • R53, R54, R55, R56, R57, Rs ⁇ , R59 and R 6 O which may be identical or different, represent a hydrogen atom or a group selected from:
  • X, X' and X which may be identical or different, representing an oxygen atom, a sulphur atom or NR with R representing a hydrogen atom or an alkyl group;
  • G represents an oxygen atom, a sulphur atom or a NR e group with R e as defined above; in particular, G represents an oxygen atom; Ri and Rh, which may be identical or different, represent a hydrogen atom or an alkyl group; it being understood that formula (XVIII) includes at least one sulphonate (O) 2 S(O " )-, M + radical or a carboxylate -C(O)O " , M + radical, preferably sodium sulphonate;
  • ⁇ R 6 i represents a hydrogen atom, a halogen atom or an alkyl group
  • ⁇ R 6 2, R ⁇ 3, and R 6 4 which may be identical or different, represent a hydrogen atom or an (O) 2 S(O " )-, M + group with M + representing a hydrogen atom or a cationic counter-ion;
  • R 6 i with R 6 2 or R 6 i with R 6 4 together form a benzo group optionally substituted with one or more (O) 2 S(O " )-, M + groups with M + representing a hydrogen atom or a cationic counter-ion; it being understood that formula (XIX) includes at least one sulphonate (O) 2 S(O " )-, M + radical, preferably sodium sulphonate.
  • dyes with formula (XII) to (XVII) which may be employed in the invention are selected from:
  • More particularly preferred anionic dyes are the dyes designated in the Colour Index with the code C.I. 58005 (monosodium salt of 1 ,2-dihydroxy-9,10- anthraquinone-3-sulphonic acid), C.I. 60730 (monosodium salt of 2-[(9,1 O- dihydro-4-hydroxy-9,10-dioxo-1-anthracenyl)-amino]-5-methyl-benzene sulphonic acid), C.I. 15510 (monosodium salt of 4-[(2-hydroxy-1 -naphthalenyl)-azo]- benzene sulphonic acid), C.I.
  • Natural direct dyes which may be used in the invention which may be cited are lawsone, juglone, alizarin, purpurin, carminic acid, kermesic acid, purpurogallin, protocatechaldehyde, indigo, isatin, curcumin, spinulosin and apigenidin. It is also possible to use extracts or decoctions containing these natural dyes and in particular cataplasms or extracts based on henna.
  • the direct dyes of the invention when they are included in the composition, are present in a proportion by weight of 0.001 % to 20%, preferably 0.01 % to 10% of the total composition weight.
  • the medium appropriate for dyeing also termed the dye support, is generally constituted by water or a mixture of water and at least one organic solvent to dissolve compounds which are not sufficiently soluble in water.
  • organic solvents which may be cited are CrC 4 lower alkanols such as ethanol or isopropanol; polyols and polyol ethers such as 2-butoxyethanol, propyleneglycol, propylene glycol monomethylether, diethylene glycol monoethylether and monomethylether, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof.
  • CrC 4 lower alkanols such as ethanol or isopropanol
  • polyols and polyol ethers such as 2-butoxyethanol, propyleneglycol, propylene glycol monomethylether, diethylene glycol monoethylether and monomethylether, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, and mixtures thereof.
  • the solvents are present in proportions which are preferably in the range about 1 % to 40% by weight with respect to the total weight of the dye composition, more preferably in the range about 5% to 30% by weight.
  • the dye composition of the invention may also comprise a variety of adjuvants which are conventionally used in hair dye compositions, such as anionic surfactants, cationic surfactants other than those with formula (I), non-ionic, amphoteric or zwittehonic surfactants or mixtures thereof, mineral or organic thickening agents, in particular associative thickeners, anionic, cationic, non ionic and amphoteric polymers, antioxidants, penetrating agents, sequestrating agents, fragrances, buffers, dispersing agents, packaging agents such as volatile or nonvolatile silicones, which may be modified or unmodified, film-forming agents, preservatives or opacifying agents.
  • adjuvants which are conventionally used in hair dye compositions, such as anionic surfactants, cationic sur
  • composition of the invention may also contain one or more fatty alcohols: R""-OH, with R"" representing an alkyl or alkenyl group containing 8 to
  • fatty alcohols being introduced in the pure form or as a mixture. More particular examples which may be cited are lauric, cetyl, stearyl or oleic alcohols and mixtures thereof.
  • the above adjuvants are generally each present in a quantity in the range 0.01 % to 20% by weight with respect to the total composition weight.
  • composition of the invention may also contain reducing agents or antioxidants. These may in particular be selected from sodium sulphite, thioglycolic acid, thiolactic acid, sodium bisulphite, dehydroascorbic acid, hydroquinone, 2-methyl-hydroquinone, ter-butyl-hydroquinone and homogentisic acid, and they are generally present in quantities of about 0.05% to 1.5% by weight with respect to the total composition weight.
  • the pH of the dye composition of the invention is generally in the range about 3 to 12, and preferably in the range about 6 to 11.5. It may be adjusted to the desired value using the acidifying agents or alkalinizing agents normally used in dyeing keratinous fibres, or by means of conventional buffer systems.
  • alkalinizing agents which may be cited are ammonia, alkaline carbonates, alkanolamines such as mono-, di- and thethanolamines as well as derivatives thereof, hydroxyalkylamines and ethylenediamines which may be oxyethylenated and/or oxypropylenated, sodium or potassium hydroxides and compounds with the following formula (XXI): in which formula (XXI):
  • W is a propylene residue, optionally substituted with a hydroxyl group or a CrC 4 alkyl radical;
  • R a , Rb, Rc and Rd which may be identical or different, represent a hydrogen atom, a Ci-C 4 alkyl radical or a CrC 4 hydroxyalkyl radical.
  • the acidifying agents are conventionally, for example, mineral or organic acids such as hydrochloric acid, orthophosphohc acid, carboxylic acids such as tartaric acid, citric acid, lactic acid or sulphonic acids.
  • the dye composition of the invention may be presented in a variety of galenical forms, such as in the form of a liquid, lotion, cream, gel, or any other form which is appropriate for dyeing keratinous fibres.
  • It may also be packaged under pressure in an aerosol flask in the presence of a propellant and may form a foam.
  • the present invention also pertains to a method for dyeing using the composition described above.
  • the dyeing method of the invention consists of applying to keratinous fibres, in particular human keratinous fibres such as the hair, the composition which comprises i) at least one oxidation base, at least one coupling agent; ii) at least one ammonium salt with formula (I), and iii) at least one ceramide; in the presence of an oxidizing agent.
  • the mixture may be produced extemporaneously, i.e. just when it is to be used, on dry or wet keratinous fibres, and then allowed to act for a time which is generally about 1 to 60 minutes, preferably about 10 to 45 minutes, then the fibres are rinsed, then optionally shampooed, then rinsed again and dried.
  • the oxidizing agent is preferably selected from hydrogen peroxide, urea peroxide, alkali metal bromates or ferricyanides and persalts such as perborates or persulphates.
  • the use of hydrogen peroxide is particularly preferred.
  • This oxidizing agent is advantageously constituted by a solution of hydrogen peroxide the titer of which may vary, more particularly from about 1 to 40 volumes, more preferably 5 to 40.
  • oxidizing agent one or more oxido- reduction enzymes such as laccases, peroxidases and 2-electron oxidoreductases such as uricase, if appropriate in the presence of their respective donor or co- factor.
  • compositions were prepared:
  • Dye compositions (expressed as the percentage by weight as is)
  • the colourant compositions were diluted extemporaneously with the oxidizing agent in an amount of 1 part of dye composition per 1.5 parts of oxidizing composition.
  • the oxidizing compositions were constituted by 20 volume hydrogen peroxide (pH close to 2-3).
  • the mixtures produced were applied to permed 90% white grey hair.
  • composition 1 and 1 ' Hair coloured with Chestnut (composition 1 and 1 '), Dark copper auburn blond (composition 2 and 2'), Black (composition 3 and 3') or Intense red (composition 4 and 4') using these compositions had good dye properties and a very good feel, in particular with dry hair.

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Abstract

La présente invention concerne une composition servant à colorer par oxydation des fibres kératiniques, notamment des fibres kératiniques humaines telles que les cheveux, cette composition comprenant, dans un milieu approprié à la coloration: i) au moins une base d'oxydation, ii) au moins un agent de couplage, iii) au moins un sel d'ammonium particulier, iv) au moins un composé céramide ou au moins un composé de polyammonium quaternaire particulier. Cette invention concerne également des méthodes de coloration et des dispositifs utilisant ladite composition. Les compositions de coloration selon l'invention présentent des propriétés cosmétiques améliorées, notamment, une excellente sensation tactile ressentie au contact de la chevelure après coloration des fibres kératiniques.
PCT/EP2007/061072 2006-10-25 2007-10-17 Composition utilisée pour colorer par oxydation des fibres kératiniques comprenant au moins un sel d'ammonium particulier dérivé de 18mea et méthode de coloration comprenant l'utilisation de ladite composition WO2008049767A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP07821437A EP2076237A1 (fr) 2006-10-25 2007-10-17 Composition utilisée pour colorer par oxydation des fibres kératiniques comprenant au moins un sel d'ammonium particulier dérivé de 18mea et méthode de coloration comprenant l'utilisation de ladite composition

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
FR0654508A FR2907671B1 (fr) 2006-10-25 2006-10-25 Composition pour la teinture des fibres keratiniques comprenant au moins un sel d'ammonium particulier derive du 18mea, au moins du ceramide et procede de coloration a partir de la composition.
FR0654511A FR2907669B1 (fr) 2006-10-25 2006-10-25 Composition pour la teinture d'oxydation des fibres keratiniques comprenant au moins un sel d'ammonium particulier derive du 18mea et procede de coloration a partir de la composition.
FR0654511 2006-10-25
FR0654508 2006-10-25
US85574106P 2006-11-01 2006-11-01
US60/855,741 2006-11-01
US85601406P 2006-11-02 2006-11-02
US60/856,014 2006-11-02

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WO2008049767A1 true WO2008049767A1 (fr) 2008-05-02

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WO (1) WO2008049767A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10716744B2 (en) 2015-06-12 2020-07-21 L'oreal Multi-step hair dyeing process using at least one titanium salt and a synthetic direct dye

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2270846A1 (fr) * 1974-05-16 1975-12-12 Oreal
EP0146350A2 (fr) * 1983-12-15 1985-06-26 Unilever Plc Composition pour le traitement des cheveux
WO1997015271A1 (fr) * 1995-10-20 1997-05-01 L'oreal Procede de teinture d'oxydation des fibres keratiniques et composition mise en oeuvre au cours de ce procede
WO2000010517A1 (fr) * 1998-08-19 2000-03-02 L'oreal Composition de teinture pour fibres keratiniques avec un colorant direct cationique et un sel d'ammonium quaternaire
DE19904359A1 (de) * 1999-02-04 2000-08-10 Wella Ag Haarpflegemittel
EP1106167A2 (fr) * 1999-12-03 2001-06-13 L'oreal Composition de teinture pour les fibres keratiniques contenant un composè non-ionique
EP1627666A1 (fr) * 2004-05-22 2006-02-22 KPSS-Kao Professional Salon Services GmbH Composition de teinture de fibres kératiniques

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2270846A1 (fr) * 1974-05-16 1975-12-12 Oreal
EP0146350A2 (fr) * 1983-12-15 1985-06-26 Unilever Plc Composition pour le traitement des cheveux
WO1997015271A1 (fr) * 1995-10-20 1997-05-01 L'oreal Procede de teinture d'oxydation des fibres keratiniques et composition mise en oeuvre au cours de ce procede
WO2000010517A1 (fr) * 1998-08-19 2000-03-02 L'oreal Composition de teinture pour fibres keratiniques avec un colorant direct cationique et un sel d'ammonium quaternaire
DE19904359A1 (de) * 1999-02-04 2000-08-10 Wella Ag Haarpflegemittel
EP1106167A2 (fr) * 1999-12-03 2001-06-13 L'oreal Composition de teinture pour les fibres keratiniques contenant un composè non-ionique
EP1627666A1 (fr) * 2004-05-22 2006-02-22 KPSS-Kao Professional Salon Services GmbH Composition de teinture de fibres kératiniques

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
T.E. GOTTSCHALCK, G.N. MCEWEN, JR.: "International Cosmetic Ingredient Dictionary and Handbook", January 2006, THE COSMETIC, TOILETRY AND FRAGRANCE ASSOCIATION, WASHINGTON, D.C., WASHINGTON, D.C., XP002437747 *
T.E. GOTTSCHALCK, G.N. MCEWEN, JR.: "International Cosmetic Ingredient Dictionary and Handbook", January 2006, THE COSMETIC, TOILETRY AND FRAGRANCE ASSOCIATION, WASHINGTON, D.C., XP002437746 *
T.E. GOTTSCHALCK, G.N. MCEWEN, JR.: "International Cosmetic Ingredient Dictionary and Handbook", January 2006, THE COSMETIC, TOILETRY AND FRAGRANCE ASSOCIATION, WASHINGTON, D.C., XP002439212 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10716744B2 (en) 2015-06-12 2020-07-21 L'oreal Multi-step hair dyeing process using at least one titanium salt and a synthetic direct dye

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