EP1836193A1 - Composes diazoiques dissymetriques, compositions les comprenant, procede de coloration et dispositif renfermant ces compositions - Google Patents

Composes diazoiques dissymetriques, compositions les comprenant, procede de coloration et dispositif renfermant ces compositions

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Publication number
EP1836193A1
EP1836193A1 EP05825515A EP05825515A EP1836193A1 EP 1836193 A1 EP1836193 A1 EP 1836193A1 EP 05825515 A EP05825515 A EP 05825515A EP 05825515 A EP05825515 A EP 05825515A EP 1836193 A1 EP1836193 A1 EP 1836193A1
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EP
European Patent Office
Prior art keywords
radical
alkyl
radicals
group
amino
Prior art date
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EP05825515A
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German (de)
English (en)
French (fr)
Inventor
Hervé David
Andrew Greaves
Nicolas Daubresse
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LOreal SA
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LOreal SA
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Publication of EP1836193A1 publication Critical patent/EP1836193A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached
    • C07D213/77—Hydrazine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
    • C09B44/12—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system having one nitrogen atom as the only ring hetero atom
    • C09B44/126—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system having one nitrogen atom as the only ring hetero atom in a six-membered ring, e.g. pyrridinium, quinolinium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
    • C09B44/16—1,3-Diazoles or hydrogenated 1,3-diazoles ; (Benz)imidazolium

Definitions

  • the subject of the present invention is particular asymmetric diazo cationic compounds and comprising a cationic or non-cationic linking arm, dyeing compositions comprising, in a medium which is suitable for dyeing keratinous fibers, such compounds as a direct dye, as well as a method for dyeing keratin fibers using this composition and a multi-compartment device.
  • the colorings that result from the use of direct dyes are temporary or semi-permanent dyes because the nature of the interactions that bind the direct dyes to the keratinous fiber, and their desorption of the surface and / or the core of the fiber are responsible their relatively low dye power and their relative poor resistance to washes or perspiration.
  • alkyl (en) radical or the alkyl (en) part of a radical is linear or branched
  • alkyl radical or the alkyl (en) part of a radical is said to be "substituted" when it comprises at least one substituent chosen from the groups:
  • An alkylcarbonylamino radical (R 1 CO-NR-) in which the radical R is a hydrogen atom or a C 1 -C 4 alkyl radical; and an alkylsulfonyl radical (R-SO 2 -) in which the radical R represents a C 1 -C 4 alkyl radical.
  • An alkylsulphinyl radical (R-SO-) in which the radical R represents a C 1 -C 4 alkyl radical.
  • R-CO- alkylcarbonyl radical in which the radical R represents a C 1 -C 4 alkyl radical.
  • a radical (hetero) cyclic, saturated or unsaturated, aromatic or otherwise, or the (hetero) cyclic, saturated or unsaturated, aromatic or non-aromatic part of a radical is said to be 'substituted' when it comprises at least one substituent, preferably carried by a carbon atom, chosen from:
  • a C 1 -C 4 alkoxy radical a (C 2 -C 4 ) polyhydroxyalkoxy radical; An amino radical;
  • R 1 CO-NR- An alkylcarbonylamino radical (R 1 CO-NR-) in which the radical R is a hydrogen atom, a C 1 -C 4 alkyl radical and the radical R 'is an alkyl radical;
  • radicals R which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical
  • An alkylsulphonylamino radical (R 1 SO 2 -NR-) in which the radical R represents a hydrogen atom, a C 1 -C 4 alkyl radical and the radical R 'represents a C 1 -C 4 alkyl radical, a phenyl radical; "An aminosulfonyl radical ((R) 2 N-SO 2 -) in which the radicals R, identical or different, represent a hydrogen atom, an alkyl radical in C 4.
  • the compounds according to the present invention are said to be asymmetrical when there is no plane of symmetry perpendicular to the linker L.
  • the two members of formula on either side of the linker L are different. More specifically, they are different when their substituents are different from their natures and / or their positions in the molecule.
  • the object of the present invention is to provide direct dyes not having the disadvantages of existing direct dyes.
  • the subject of the present invention is therefore asymmetric, cationic diazo compounds of formula (I) below, their resonant forms, as well as their addition salts with an acid and / or their solvates:
  • radicals R 2 identical or different, independently of one another, represent:
  • an alkyl radical -C 16 optionally substituted, optionally interrupted by one or more heteroatoms and / or by one or more groups comprising at least one heteroatom, preferably selected from oxygen, nitrogen, sulfur, -CO- , -SO 2 - or combinations thereof; said alkyl group being further optionally substituted by one or more identical or non moieties chosen from thio (-SH), thio C 1 -C 4 alkyl; alkyl (C 1 -C 4 ) sulfinyl, C 1 -C 4 alkylsulphonyl;
  • R represents a C 1 -C 4 alkyl radical.
  • RCO-O- alkylcarbonyloxy radical in which R represents a C 1 -C 4 alkyl radical.
  • R-CO- An alkylcarbonyl radical in which R represents a C 1 -C 4 alkyl radical. "An amino group.
  • RCO-NR'- An alkylcarbonylamino group in which the radical R represents a C 1 -C 4 alkyl radical and the radical R 'represents a hydrogen or a C 1 -C 4 alkyl radical;
  • An aminocarbonyl group ((R) 2 N-CO-) in which the radicals R independently of one another represent a hydrogen atom or a C 1 -C 4 alkyl radical;
  • a ureido group (N (R) 2 -CO-NR'-) in which the radicals R and R ', independently of each other, represent a hydrogen atom or a Ci-C 4 alkyl radical;
  • An aminosulphonyl group ((R) 2 N-SO 2 -) in which the radicals R independently of one another represent a hydrogen atom or a C 1 -C 4 alkyl radical;
  • An alkylsulphonylamino group (RSO 2 -NR'-) in which R represents a C 1 -C 4 alkyl radical; R 'represents a hydrogen atom, a C 1 -C 4 alkyl radical;
  • R-SO 2 - An alkylsulphonyl group (R-SO 2 -) in which R represents a C 1 -C 4 radical;
  • a halogen atom preferably chlorine or fluorine
  • an alkylthio group in which the radical R represents an optionally substituted C 1 -C 4 alkyl radical;
  • the two radicals R 2 may optionally form, with the carbon atoms to which they are attached, a secondary cycle, aromatic or nonaromatic, 5- or 6-membered, preferably 6-membered, optionally substituted by one or more groups, identical or different, chosen from hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 ( poly) C 2 -C 4 hydroxyalkoxy, amino, amino substituted with one or two identical or different C 1 -C 4 alkyl radicals, optionally carrying at least one hydroxyl group;
  • e is an integer from 0 to 4; when e is less than 4, the carbon atom (s) of the unsubstituted heterocycle carry a hydrogen atom.
  • the radicals R 3, which may be identical or different, independently of each other represent: a C 1 -C 16 alkyl radical, optionally substituted, optionally interrupted by one or more heteroatoms or by one or more groups comprising at least one heteroatom, preferably selected from oxygen, nitrogen, sulfur, -CO-, -SO 2 - or combinations thereof.
  • RO-CO- an alkoxycarbonyl group in which R represents a C 1 -C 4 alkyl radical.
  • RCO-O- An alkylcarbonyloxy radical (RCO-O-) in which R represents a C 1 -C 4 alkyl radical
  • R-CO- alkylcarbonyl radical in which R represents a C 1 -C 4 alkyl radical
  • RCO-NR'- an alkylcarbonylamino group in which the radical R is an alkyl radical C 4 and the radical R 'represents a hydrogen atom or an alkyl radical in C 1 -C 4 alkyl;
  • An aminocarbonyl group ((R) 2 N-CO-) in which the radicals R independently of one another represent a hydrogen atom or a C 1 -C 4 alkyl radical;
  • a ureido group (N (R) 2 -CO-NR'-) in which the radicals R and R ', independently of each other, represent a hydrogen atom or a C 1 -C 4 alkyl radical; . an aminosulphonyl group ((R) 2 N-SO 2 -) in which the radicals R independently of one another represent a hydrogen atom or a C 1 -C 4 alkyl radical;
  • An alkylsulphonylamino group (RSO 2 -NR'-) in which the radicals R, R ', independently of each other, represent a hydrogen atom or a C 1 -C 4 alkyl radical; . a thio group (HS-); . an alkylthio group (RS-) in which the radical R represents a C 1 -C 4 alkyl radical;
  • a halogen atom preferably chlorine or fluorine
  • two adjacent radicals R 3 can form, with the carbon atoms to which they are attached, a secondary ring, aromatic or non-aromatic with 6 members, optionally substituted by one or more identical or different groups chosen from hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 (poly) hydroxyalkoxy, C 2 -C 4 alkylcarbonylamino, C 1 -C 4 alkyl, amino, amino substituted by one or two alkyl radicals C 1 -C 4 identical or different and optionally carrying at least one hydroxyl group.
  • m ' is an integer from 0 to 4; when m 'is less than 4, then the unsubstituted aromatic ring carbon atom (s) carry a hydrogen atom; Wi identical or not, independently of each other represent:. a hydrogen atom
  • a halogen atom selected from bromine, chlorine, fluorine, preferably chlorine and fluorine.
  • R 4 , R 7 which may be identical or different, represent a hydrogen atom, an optionally substituted C 1 -C 2 0, preferably C 1 -C 16 , alkyl radical or an optionally substituted C 1 -C 3 aralkyl radical; substituted, an optionally substituted phenyl radical;
  • R 5 and R 6 which are identical or different, represent a hydrogen atom, an optionally substituted C 1 -C 20 , preferably C 1 -C 16 , alkyl radical, an optionally substituted phenyl radical or a C 1 -C 6 aralkyl radical;
  • Optionally substituted 3 an alkylcarbonyl radical (R-CO-) wherein R is a C 1 -C 4 alkyl radical;
  • R 5 and R 6 may optionally form, with the nitrogen atom to which they are attached, a heterocycle containing 1 to 3 heteroatoms, preferably 1 to 2 heteroatoms, chosen from N, O, S, preferably N, comprising from 5-7 membered, saturated or unsaturated, aromatic or otherwise, optionally substituted;
  • R 5 and R 6 can form with the carbon atom of the aromatic ring adjacent to which to -NR 5 R 6 , is attached, a saturated heterocycle with 5 or 6 members;
  • Ph represents an optionally substituted phenyl radical
  • L is a cationic linking arm or not
  • the electroneutrality of the compound of formula (I) being provided by one or more cosmetically acceptable anions An, which may be identical or different.
  • the present invention also relates to dye compositions comprising, in a medium suitable for dyeing keratinous fibers, such compounds, or their addition salts with an acid, as direct dyes.
  • It further relates to a method for dyeing keratinous fibers comprising contacting a composition according to the invention with said fibers, dry or wet, for a time sufficient to obtain the desired effect.
  • a multi-compartment device comprising, in a first compartment, the composition according to the invention, and in a second compartment, an oxidizing composition.
  • the compounds of formula (I) as defined above have a good toughness vis-à-vis external agents such as shampoos, and this, even when the keratin fiber is sensitized. Moreover, these compounds have improved dyeing properties such as chromaticity, coloring power and low selectivity, that is to say that the compounds of the invention make it possible to obtain more uniform colorations between the tip and the hairline.
  • a first subject of the invention consists of compounds corresponding to the aforementioned formula (I) as well as their salts and / or solvates.
  • the compounds of formula (I) according to the present invention are such that the radicals R 2 , which may be identical or different, independently of one another, preferably represent:
  • a halogen atom chosen from chlorine or fluorine; a C 1 -C 4 alkyl radical, optionally substituted with one or more radicals chosen, which may be identical or different, from hydroxyl, C 1 -C alkoxy, (C 2 -C 4 ) poly (C 2 -C 4 ) polyoxyalkoxy, amino, (di) alkylamino radicals, C 1 -C 2 alkyl, thio (-SH), (C r -C 4) alkylsulfinyl, (Ci-C 4) alkylsulfonyl, thioalkyl (C r C 4);
  • a phenyl radical optionally substituted with one or more radicals chosen from hydroxyl, C 1 -C 2 alkoxy, (C 2 -C 4 ) (poly) hydroxyalkoxy, amino, (di) C 1 -C 2 alkylamino radicals, or a halogen atom such as chlorine, fluorine
  • an alkylsulphonylamino radical (RSO 2 N-) in which the radical R represents a C 1 -C 4 alkyl radical
  • an aminosulphonyl radical ((R) 2 NSO 2 -) in which the radicals R independently of one another represent a hydrogen atom or a C 1 -C 4 alkyl radical
  • an alkylthio radical in which the radical R represents a C 1 -C 4 alkyl radical.
  • an alkylsulfinyl radical RSO- in which the radical R represents a C 1 -C 4 alkyl radical.
  • R-SO 2 - an alkylsulphonyl radical in which the radical R represents a C 1 -C 4 alkyl radical
  • RCONR'- an alkylcarbonylamino radical in which the radical R represents a hydrogen atom, a C 1 -C 4 alkyl radical and the radical R 'represents a hydrogen atom or a C 1 -C alkyl radical; 4 .
  • the radicals R 2 which may be identical or different, independently of one another, preferably represent a methyl, ethyl, 2-hydroxyethyl, 2-methoxyethyl, methylsulfonyl (CH 3 SO 2 -) or methylcarbonylamino (CH 3 ) radical.
  • 3 CONH-) hydroxyl, amino, methylamino, dimethylamino, 2-hydroxyethylamino, methoxy, ethoxy, phenyl.
  • two radicals R 2 may optionally form, with the carbon atoms to which they are attached, a secondary, aromatic, 6-membered ring, optionally substituted with one or more groups.
  • identical or different chosen from hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, amino, amino substituted by one or two alkyl radicals C 1 -C 4 identical or different and optionally bearing at least one hydroxyl or methylcarbonylamino group.
  • two radicals R 2 may optionally form, with the carbon atoms to which they are attached, a secondary 6-membered aromatic ring, optionally substituted by one or more radicals which may be identical or different, chosen from hydroxyl, methoxy and ethoxy, amino, acylamino, 2-hydroxyethylamino, dimethylamino, (di) -2-hydroxyethylamino, methylcarbonylamino.
  • the coefficient e is equal to 0.
  • radicals R 3 which are identical or different, independently of one another, more particularly represent: a C 1 -C 16 , preferably C 1 -C 8 , alkyl radical which is optionally substituted; ; a halogen atom such as chlorine, fluorine;
  • hydroxyl group a C 1 -C 2 alkoxy radical; a (poly) -hydroxyalkoxy (C 2 -C 4) radical;
  • an amino radical an amino radical substituted with one or two identical or different C 1 -C 4 alkyl radicals optionally bearing at least one hydroxyl group or at least one C 1 -C 4 alkoxy radical, the two alkyl radicals being able to form with the nitrogen atom to which they are attached, a heterocycle containing 1 to 3 heteroatoms, preferably 1 to 2 heteroatoms, chosen from N, O, S, preferably N, the 5- to 7-membered heterocycle being saturated; or unsaturated, aromatic or not, and optionally substituted;
  • RCO-NR'- an alkylcarbonylamino radical in which the radical R represents a C 1 -C 4 alkyl radical and the radical R 'represents a hydrogen, an alkyl radical
  • Ci-C 4 Ci-C 4 ; an alkylsulphonylamino radical (R 1 SO 2 -NR-) in which the radical R represents a hydrogen atom or a C 1 -C 4 alkyl radical, the radical R 'represents a C 1 -C 4 alkyl radical; an aminosulfonyl radical ((R) 2 N-SO 2 -) in which the radicals R, which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl radical;
  • radical R-SO 2 - an alkylsulphonyl radical (R-SO 2 -) in which the radical R represents a C 1 -C 4 alkyl radical. More preferably, said radicals R 3 , which are identical or different, independently of one another, represent:
  • alkyl radical in C 1 -C 4 optionally substituted by one or more radicals identical or not chosen from hydroxyl, alkylcarbonylamino, C 1 -
  • C 2 amino substituted with two identical or different C 1 -C 2 alkyl radicals and optionally bearing at least one hydroxyl group or a C 1 -C 2 alkoxy radical; these two alkyl radicals may optionally form, with the nitrogen atom to which they are attached, a 5- or 6-membered heterocycle, saturated or unsaturated, optionally aromatic, preferably chosen from pyrrolidine, piperazine, homopiperazine and pyrrole; imidazole, pyrazole;
  • halogen chosen from chlorine or fluorine; an amino radical; an amino radical substituted with one or two identical or different C 1 -C 2 alkyl radicals and optionally bearing at least one hydroxyl group;
  • hydroxyl radical a C 1 -C 2 alkoxy radical; a methylsulfonyl radical.
  • the radicals R 3 independently of each other, preferably represent: a methyl, ethyl, propyl, 2-hydroxyethyl, methoxy, ethoxy, 2-hydroxyethyloxy, 3-hydroxypropyloxy or 2-methoxyethyl radical;
  • two adjacent radicals R 3 may form, with the carbon atoms to which they are attached, a 6-membered aromatic secondary ring, optionally substituted by one or more identical or different groups chosen from hydroxyl groups,
  • two adjacent radicals R 3 can form, with the carbon atoms to which they are attached, a 6-membered aromatic secondary ring, optionally substituted with one or more identical or different groups chosen from hydroxyl, methoxy, ethoxy, 2-hydroxyethyloxy, amino, methylcarbonylamino, (di) 2-hydroxyethylamino, -NH-Ph, -NH-Ph-NH 2, -NH-Ph-NHCOCH 3, -NH-Ph-OH 1 -NH-Ph-OCH 3 .
  • radicals R 4 and R 7 represent: a hydrogen atom
  • an aryl or arylalkyl radical such as phenyl or benzyl, the aryl part being optionally substituted with one or more radicals that are identical or different, chosen from chlorine, amino, hydroxyl, C 1 -C 2 alkoxy, mono or di-substituted amino; or two identical or different C 1 -C 4 alkyl radicals and optionally bearing at least one hydroxyl group.
  • radicals R 4 and R 7 represent:
  • C 1 -C 3 alkyl radical such as methyl, ethyl, 2-hydroxyethyl or 2-methoxyethyl
  • a phenyl radical optionally substituted with one or more radicals chosen from hydroxyl, C 1 -C 2 alkoxy, amino and amino radicals substituted with one or more C 1 -C 4 groups optionally bearing at least one hydroxyl group;
  • radicals R 4 and R 7 represent: a hydrogen atom
  • a phenyl radical optionally substituted by a hydroxyl, methoxy, amino, (di) methylamino or (di) (2-hydroxyethyl) amino radical.
  • radicals R 5 , R 6 identical or not independently of one another, the latter more particularly represent:
  • R-CO- an alkylcarbonyl radical in which R represents an optionally substituted C 1 -C 4 alkyl radical.
  • R represents an optionally substituted C 1 -C 4 alkyl radical.
  • an optionally substituted C 1 -C 6 alkyl radical preferably one or more identical or different groups chosen from hydroxyl and C 1 -C 2 alkoxy, amino, (di-) alkylamino -C 4; the alkyl group may further be substituted by at least one -C 4 alkylsulfonyl group, at least one alkylsulfinyl group Ci-C 4, at least an alkylcarbonyl group in Ci-C 4.
  • an aryl or arylalkyl radical such as phenyl or benzyl, the aryl part being optionally substituted by one or more identical or different groups chosen from chlorine, amino, hydroxyl, C 1 -C 4 alkoxy, amino mono- or di-substituted with one or two identical or different C 1 -C 4 alkyl radicals and optionally bearing at least one hydroxyl group.
  • radicals R 5 , R 6 which are identical or different, independently of each other advantageously represent:
  • a hydrogen atom a methylcarbonyl, ethylcarbonyl or propylcarbonyl radical; an optionally substituted C 1 -C 3 alkyl radical, such as methyl, ethyl, 2-hydroxyethyl, 2-methoxyethyl;
  • a phenyl radical optionally substituted with one or more radicals chosen from hydroxyl, C 1 -C 2 alkoxy, amino and amino radicals substituted by one or more C 1 -C 4 groups optionally bearing at least one hydroxyl group.
  • radicals R 5 , R 6 which are identical or different, independently of one another, represent:
  • a methyl, ethyl, 2-hydroxyethyl radical a methylcarbonyl, ethylcarbonyl or propylcarbonyl radical
  • a phenyl radical optionally substituted by a hydroxyl, methoxy, amino, (di) methylamino or (di) (2-hydroxyethyl) amino radical;
  • the radicals R 5 and R 6 together with the nitrogen atom to which each is attached, form a heterocycle containing 1 to 3 heteroatoms, preferably 1 to 2 heteroatoms, chosen from N, O, S, preferably N, comprising from 5 to 7 members, saturated or unsaturated, aromatic or otherwise, optionally substituted.
  • the 5- to 7-membered heterocycle is chosen from the following heterocycles: piperidine, 2- (2-hydroxyethylpiperidine), 4- (aminomethyl) piperidine, 4- (2-hydroxyethyl) piperidine, 4- (dimethylamino) piperidine, piperazine, 1-methylpiperazine, 1- (2-hydroxyethyl) piperazine, 1- (2-aminoethyl) piperazine, 1-hydroxyethylethoxy piperazine, homopiperazine, 1-methyl-1,4-perhydrodiazepine, pyrrole, 1,4-dimethylpyrrole 1-methyl-4-ethylpyrrole, 1-methyl-4-propylpyrrole.
  • the 5- to 7-membered heterocycle represents a heterocycle of piperidine, piperazine, homopiperazine, pyrrole, imidazole or pyrazole type optionally substituted by one or more methyl, hydroxyl or amino (di) methylamino radicals.
  • the radicals R 5 and R 6 form, with the carbon atom of the aromatic ring optionally substituted by a hydroxyl and adjacent to that to which NR 5 R 6 is attached, a saturated heterocycle with 5 or 6 members. .
  • the group -NR 5 R 6 with the aromatic ring optionally substituted with a hydroxyl may correspond to the following compounds:
  • L is a non-cationic linker
  • the non-cationic linking arm connecting the two different azo chromophores represents:
  • alkyl C 1 -C 4 O preferably C 1 -C 2O, optionally substituted, optionally interrupted by a (hetero) saturated or unsaturated ring, aromatic or nonaromatic, comprising from 3 to 7 members, optionally substituted, optionally condensed; said alkyl radical being optionally interrupted by one or more heteroatoms or groups comprising at least one heteroatom, preferably oxygen, nitrogen, sulfur, -CO-, -SO 2 - or combinations thereof; the linking arm L not including azo bond, nitro, nitroso, peroxo;
  • the linker is cationic.
  • the cationic linking arm linking the two different azo chromophores represents a C 2 -C 40 alkyl radical carrying at least one cationic charge, optionally substituted and / or optionally interrupted by one or more (hetero) rings.
  • the linking arm L not including azo bond, nitro, nitroso, peroxo; Given that the link arm L carries at least one cationic charge.
  • L represents a non-cationic linker.
  • alkyl-type linking arm L mention may be made of the methylene, ethylene, linear or branched propylene, linear or branched butylene, linear or branched pentylene or linear or branched hexylene radicals, optionally substituted. and / or interrupted as indicated above.
  • substituents are preferably selected from hydroxyl, alkoxy, C 1 -C 2 dialkylamino, C 1 -C 2 ralkyl (C r C 4) carbonyl, alkyl (C 4 -C ) alkylsulfonyl.
  • ring or heterocycle saturated or unsaturated, aromatic or non-aromatic, interrupting the alkyl radical of the linking arm L
  • linker L By way of example of linker L, mention may be made of methylene, ethylene, linear or branched propylene, linear or branched butylene, linear or branched pentylene or linear or branched hexylene radicals, optionally substituted and / or interrupted as indicated above. above.
  • saturated or unsaturated, saturated or unsaturated aromatic or non-aromatic ring or heterocycle interrupting the alkyl radical of the linking arm L mention may be made of phenylene or naphthylene, phenanthrylene, triazinyl, pyrimidinyl, pyridinyl, pyridazinyl and quinoxalinyl radicals. cyclohexyl
  • radicals L are suitable:
  • O n is an integer between 0 and 4
  • n '" is an integer from 0 to 3
  • R ' has the same definition as R 3 ;
  • R refers to a hydrogen, a C 1 -C 4 alkyl radical.
  • R 8 and R 9 represent, independently of one another, a hydrogen atom or a C 1 -C 6 alkyl radical optionally substituted by one or more identical or different radicals chosen from hydroxyl and C 1 -C 2 alkoxy, poly) C 2 -C 4 hydroxyalkoxy, amino, C 1 -C 2 (di) alkylamino or optionally substituted aryl.
  • n is an integer from 0 to 4
  • Aromatic ring positions not substituted by a methyl radical carry a hydrogen atom
  • L represents a cationic linker.
  • the cationic L bonding arm advantageously represents a C 2 -C 20 alkyl radical:
  • R 9 and R 10 independently of one another, represent a C 1 -C 8 alkyl radical; a C 1 -C 6 monohydroxyalkyl radical; a C 2 -C 6 polyhydroxyalkyl radical; alkoxy (C r C 6) alkyl C 1 -C 6 alkyl; an aryl radical such as optionally substituted phenyl; an arylalkyl radical such as optionally substituted benzyl; a C 1 -C 6 aminoalkyl radical; a C 1 -C 6 aminoalkyl radical, the amine of which is substituted by one or two identical or different C 1 -C 4 alkyl radicals, a (C 1 -C 6 ) alkylsulphonyl radical.
  • Two radicals R 9 may together form, with the nitrogen atom to which they are attached, a saturated or unsaturated, optionally substituted, 5-, 6- or 7-membered ring.
  • R 13 which may be identical or different, represent a halogen atom chosen from bromine, chlorine or fluorine, a C 1 -C 6 alkyl radical, a radical monohydroxyalkyl, C 1 -C 6 polyhydroxyalkyl radical, C 2 -C 6, alkoxy C 1 -C 6 alkyl group, a (di) alkylamino, C 1 -C 4 alkyl, a hydroxycarbonyl group, an alkylcarbonyl C 1 -C 6 thioalkyl radical C 1 -C 6 alkyl radical (C r C 6) alkylthio, an alkyl (C r -C 6) sulfonyl, an optionally substituted benzyl radical, a phenyl radical optionally substituted by one or more radicals chosen from methyl, hydroxyl, amino and methoxy radicals.
  • a halogen atom chosen from bromine, chlorine or fluorine
  • An is an anion or a mixture of anions, organic or mineral
  • Z is an integer from 1 to 3; if z ⁇ 3, then the unsubstituted carbon atoms carry a hydrogen atom.
  • v is an integer equal to 1 or 2, preferably 1.
  • 2- optionally interrupted by one or more heteroatoms or groups comprising at least one heteroatom or combinations thereof, such as, for example, oxygen, nitrogen, sulfur, a group -CO-, a group -SO 2 -; provided that there is no nitro, nitroso or peroxo group or bond in the linker L;
  • Rg, R 10 are preferably chosen from a C 1 -C 6 alkyl radical, a C 1 -C 4 monohydroxyalkyl radical and a radical.
  • R 9 and R 10 separately represent a methyl, ethyl, 2-hydroxyethyl radical.
  • R represents a halogen atom chosen from chlorine and fluorine, an alkyl radical C 1 -C 6 monohydroxylalkyle radical C 1 -C 4 , a C 1 -C 4 alkoxy radical, a hydroxycarbonyl radical, an alkyl (CrCe) thio radical, an amino radical disubstituted by a (C 1 -C 4 ) alkyl radical.
  • R 13 represents a chlorine atom, a methyl, an ethyl, a 2-hydroxyethyl, a methoxy, a hydroxycarbonyl, a dimethylamino.
  • An represents an anion or a mixture of organic or inorganic anions making it possible to balance the charge (s) of the compounds of formula (I), for example chosen from a halide such as chloride, bromide, fluoride, iodide; a hydroxide; sulphate; a hydrogen sulfate; an alkyl sulphate for which the linear or branched alkyl part is C 1 -C 6 , such as the methyl sulphate or ethyl sulphate ion; carbonates and hydrogen carbonates; salts of carboxylic acids such as formate, acetate, citrate, tartrate, oxalate; alkylsulphonates for which the linear or branched alkyl moiety is C 1 -C 6 such as the methylsulfonate ion; arylsulphonates for which the aryl part,
  • a halide such as chloride, bromide, fluoride, iodide
  • the acid addition salts of the compounds of formula (I) may be by way of example the addition salts with an organic or inorganic acid such as hydrochloric acid, hydrobromic acid, sulfuric acid or (alkyl- or phenyl) sulfonic acids such as p-toluenesulphonic acid or methylsulphonic acid.
  • an organic or inorganic acid such as hydrochloric acid, hydrobromic acid, sulfuric acid or (alkyl- or phenyl) sulfonic acids such as p-toluenesulphonic acid or methylsulphonic acid.
  • the solvates of the compounds of formula (I) represent the hydrates of such compounds as well as the combination of these compounds with a linear or branched C 1 -C 4 alcohol, such as methanol, ethanol, isopropanol, naphthalene and the like. propanol.
  • the compounds correspond to the following formulas (I '), (I ") or (I 1 "), as well as their resonant forms and / or their addition salts with an acid and / or their solvates:
  • R 2 , n ', An have the same meanings as before.
  • the compounds correspond to one of the following formulas, as well as their resonant forms, their addition salts with an acid and / or their solvates:
  • the compounds corresponding to the monoazo species can in particular be obtained from the preparation processes described for example in the documents US Pat. No. 5,708,151, J. Chem. Res .., Synop. (1998), (10), 648-649, US3151106, US5852179, Heterocycles, 1987, 26 (2) 313-317, Synth. Common 1999, 29 (13), 2271-2276, Tetrahedron, 1983, 39 (7), 1091-1101.
  • Another subject of the present invention consists of a dyeing composition
  • a dyeing composition comprising, in a medium suitable for dyeing keratinous fibers, at least one compound of formula (I), its addition salts with an acid and / or its solvates, as a direct dye.
  • the total concentration of compound (s) of formula (I) may vary between 0.001 and 20% by weight relative to the total weight of the dyeing composition, more particularly between 0.01 and 10% by weight, and preferably between 0, 05 and 5% by weight.
  • the dye composition according to the invention may further comprise a base oxidation.
  • This oxidation base may be chosen from the oxidation bases conventionally used in oxidation dyeing, for example para-phenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases.
  • para-phenylenediamine para-phenylenediamine, paratoluylenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine and 2,6-diethyl-para-phenylenediamine may be mentioned by way of example; , 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, N, N-bis- ( ⁇ -hydroxyethyl) paraphenylenediamine, 4-N, N-bis- ( ⁇ -hydroxyethyl) amino-2-methylaniline, 4-N, N-bis- ( ⁇ -hydroxyethyl)
  • N- (4'-aminophenyl) paraphenylenediamine N-phenyl paraphenylenediamine, 2- ⁇ -hydroxyethyloxy para-phenylenediamine, 2- ⁇ -acetylaminoethyloxy para-phenylenediamine, N- ( ⁇ -methoxyethyl) paraphenylenediamine, 4-aminophenylpyrrolidine, 2-thienyl paraphenylene diamine, 2- ⁇ -hydroxyethylamino-5-amino toluene and their addition salts with an acid.
  • paraphenylenediamine paratoluylenediamine, 2-isopropyl paraphenylenediamine, 2- ⁇ -hydroxyethyl paraphenylenediamine, 2- ⁇ -hydroxyethyloxy paraphenylenediamine, 2,6-dimethyl paraphenylenediamine, 2,6-diethyl paraphenylenediamine, 2,3-dimethyl paraphenylenediamine, N, N-bis- ( ⁇ -hydroxyethyl) paraphenylenediamine, 2-chloro-para-phenylenediamine, 2- ⁇ -acetylaminoethyloxy-para-phenylenediamine, and their acid addition salts are particularly preferred .
  • N N'-bis- ( ⁇ -hydroxyethyl) N
  • N'-bis (4'-aminophenyl) -1,3-diamino propanol, N may be mentioned by way of example.
  • para-aminophenol para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluoro phenol, 4-amino-3-hydroxymethylphenol, 4- amino 2-methyl phenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- ( ⁇ -hydroxyethylaminomethyl) phenol, 4- amino 2-fluoro phenol, and their addition salts with an acid.
  • ortho-aminophenols mention may be made, for example, of 2-amino phenol, 2- amino-5-methylphenol, 2-amino-6-methylphenol, 5-acetamido-2-amino phenol, and their addition salts with an acid.
  • heterocyclic bases that may be mentioned by way of example are 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-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 mention may be made of the compounds described, for example, in DE 2 359 399; JP 88-169,571; JP 05 163 124; EP 0 770 375 or patent application WO 96/15765 such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy 2,5,6-triaminopyrimidine, 2-hydroxy 4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine, and 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-dimethyl pyrazolo [1,5-a] pyrimidine-3,7-diamine; pyrazolo [1,5-a] pyrimidine-3,5-diamine
  • the dye composition according to the invention may also contain one or more couplers conventionally used for dyeing keratinous fibers.
  • couplers there may be mentioned meta-phenylenediamines, meta-aminophenols, meta-diphenois, naphthalenic couplers and heterocyclic couplers.
  • the oxidation base (s) are present in a total amount, preferably of between 0.001% to 10% by weight relative to the total weight of the dyeing composition, and more preferably from 0.005% to 6% by weight.
  • the coupler (s) are generally present in a total amount of between 0.001% and 10% by weight relative to the total weight of the dyeing composition and more preferably from 0.005% to 6% by weight.
  • addition salts with an acid that can be used in the context of the dyeing compositions of the invention for the oxidation bases and the couplers are in particular chosen from those listed in the context of the definition of the compounds of formula
  • composition according to the invention may optionally comprise at least one additional direct dye different from the compounds of formula (I). This can be chosen from cationic or nonionic species.
  • nitrobenzene dyes such as nitrobenzene dyes, azo, azomethine, methine, tetraazapenthamethine, anthraquinone, naphthoquinone, benzoquinone, phenotiazine indigo, xanthene, phenanthridine, phthalocyanine dyes, those derived from triarylmethane and natural dyes. alone or in mixtures.
  • red or orange nitrobenzene dyes It may for example be chosen from the following red or orange nitrobenzene dyes:
  • the additional direct dye may also be chosen from the yellow and yellow-green nitro benzene direct dyes, for example compounds selected from:
  • Rb represents a C1-C4 alkyl radical, a ⁇ -hydroxyethyl or ⁇ -hydroxypropyl or ⁇ -hydroxypropyl radical;
  • Ra and Rc which are identical or different, represent a ⁇ -hydroxyethyl, - ⁇ -hydroxypropyl, ⁇ -hydroxypropyl or ⁇ , ⁇ -dihydroxypropyl radical, at least one of Rb, Rc or Ra radicals representing a ⁇ -hydroxypropyl radical; and Rb and Rc can not simultaneously designate a ⁇ -hydroxyethyl radical when Rb is a ⁇ -hydroxypropyl radical, such as those described in French patent FR 2,692,572.
  • the following dyes may be mentioned in particular: 1,3-dimethyl-2 - [[4- (dimethylamino) phenyl] azo] -1H-imidazolium chloride, 1,3-dimethyl-2-chloride [ (4-Aminophenyl) azo] -1H-imidazolium, 1-methyl-4 - [(methylphenylhydrazono) methyl] -pyridinium methylsulfate.
  • Other azo direct dyes that may be mentioned include the following dyes, described in the COLOR INDEX INTERNATIONAL 3rd edition: -Disperse Red 17-Acid Yellow 9-Acid Black 1 -Basic Red 22 -Basic Red 76
  • triarylmethane dyes that can be used according to the invention, mention may be made of the following compounds: -Basic Green 1
  • indoamine dyes that can be used according to the invention, mention may be made of the following compounds:
  • the content of additional direct dye (s) in the composition generally varies from 0.001 to 20% by weight relative to the weight of the composition, and preferably from 0.01 to 10% by weight. weight relative to the weight of the composition.
  • the appropriate medium for dyeing also called dyeing medium, is generally constituted by water or a mixture of water and at least one organic solvent to solubilize compounds that are not sufficiently soluble in water .
  • the organic solvents are chosen from monoalcohols or diols, linear or branched, preferably saturated, comprising 2 to 10 carbon atoms, such as ethyl alcohol, isopropyl alcohol, hexylene glycol (2-methyl 2, 4- pentanediol), neopentyl glycol and 3-methyl-1,5-pentanediol; aromatic alcohols such as benzyl alcohol, phenylethyl alcohol; glycols or glycol ethers such as, for example, ethylene glycol monomethyl, monoethyl and monobutyl ethers, propylene glycol or its ethers such as, for example, propylene glycol monomethyl ether, butylene glycol, dipropylene glycol; as well as the alkyl ethers of diethylene glycol, especially of C 1 -C 4 , such as, for example, diethylene glycol monoethyl ether or monobutyl ether, alone or as a mixture
  • the dyeing composition in accordance with the invention may also contain various adjuvants conventionally used in compositions for dyeing hair, such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic polymers.
  • ionic, amphoteric, zwitterionic or mixtures thereof inorganic or organic thickeners, and in particular anionic, cationic, nonionic and amphoteric polymeric associative thickeners, antioxidants, penetration agents, sequestering agents, perfumes, buffers , dispersing agents, conditioning agents such as, for example, volatile or non-volatile silicones, modified or unmodified, film-forming agents, ceramides, preserving agents, opacifying agents.
  • the pH of the dye composition according to the invention is generally between 3 and 12 approximately, and preferably between 5 and 11 approximately. It can be adjusted to the desired value by means of acidifying or alkalizing agents usually used for dyeing keratin fibers or else using conventional buffer systems.
  • acidifying agents mention may be made, by way of example, of mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulphonic acids.
  • mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulphonic acids.
  • alkalinizing agents that may be mentioned, by way of example, are ammonia, alkaline carbonates, alkanolamines such as mono-, di- and triethanolamines and their derivatives, sodium or potassium hydroxides and following formula:
  • W is a propylene residue optionally substituted by a hydroxyl group or a C 1 -C 4 alkyl radical
  • R 3, R b, R c and R d, identical or different, represent a hydrogen atom, an alkyl radical in C 1 -C 4 hydroxyalkyl or C 1 -C 4.
  • the dye composition 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 keratinous fibers, and especially human hair.
  • composition according to the invention may further comprise at least one oxidizing agent.
  • at least one oxidizing agent we speak of ready-to-use compositions.
  • ready-to-use composition in the sense of the present invention, the composition intended to be applied immediately to the keratinous fibers, that is to say that it can be stored as it is before use or result from extemporaneous mixing of two or more compositions. Said composition can also be obtained by mixing the composition according to the invention with an oxidizing composition.
  • the oxidizing agent can be any oxidizing agent conventionally used in the field. Thus, it may be chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulphates, as well as the enzymes among which may be mentioned peroxidases, oxides, 2-electron reductases such as uricases and 4-electron oxygenases such as laccases.
  • the use of hydrogen peroxide is particularly preferred.
  • the content of oxidizing agent is generally between 1 and 40% by weight, relative to the weight of the ready-to-use composition, preferably between 1 and 20% by weight relative to the weight of the ready-to-use composition. .
  • the oxidizing composition used is an aqueous composition and may be in the form of a solution or an emulsion.
  • the oxidant-free composition is mixed with about 0.5 to 10 equivalents by weight of the oxidizing composition.
  • the pH of the ready-to-use composition is more particularly between 4 and 12, preferably between 7 and 11.5.
  • the pH of the composition may be adjusted by means of an alkalinizing or acidifying agent, chosen in particular from those mentioned above, in the context of the description according to the invention.
  • the subject of the invention is also a dyeing method which comprises the application of a dyeing composition according to the invention to keratinous fibers, dry or wet.
  • the application to the fibers of the dye composition comprising the compound (s) of formula (I) or its addition salts with an acid, optionally at least one oxidation base optionally associated with at least one coupler, optionally at least one additional direct dye can be carried out in the presence of an oxidizing agent.
  • This oxidizing agent may be added to the composition comprising the compound (s) of formula (I) and any additional oxidation bases, couplers and / or direct dyes, either at the time of use or directly on the keratinous fiber. .
  • the oxidizing composition may also contain various adjuvants conventionally used in compositions for dyeing hair and as defined above.
  • 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 fibers preferably varies between 4 and 12 approximately, and even more preferably between 7 and 11. 5. It can be adjusted to the desired value by means of acidifying or alkalizing agents usually used in dyeing keratinous fibers and as defined above.
  • composition which is finally applied to the keratin fibers may be in various forms, such as in the form of liquids, creams, gels or in any other form suitable for dyeing keratinous fibers, and especially human hair.
  • the composition according to the invention is free of oxidation base and coupler.
  • the composition applied may optionally comprise at least one oxidizing agent.
  • the composition is therefore applied to the keratin fibers, dry or wet, and then left for a sufficient exposure time to obtain the desired color.
  • the exposure time is generally between a few seconds and one hour, preferably between 3 and 30 minutes.
  • the temperature at which the composition is allowed to act is in general between 15 and 220 ° C., more particularly between 15 and 80 ° C., preferably between 15 and 40 ° C.
  • the composition is preferably removed by rinsing with water, optionally followed by washing with a shampoo, then optionally drying.
  • Another object of the invention is a multi-compartment device or "kit” of dyeing in which a first compartment contains the dye composition of the invention and a second compartment contains the oxidizing composition.
  • This device may be equipped with means for delivering the desired mixture onto the hair, such as the devices described in patent FR-2,586,913.
  • Compound 1 is commercially available (INTERCHIM).
  • the 1 H and mass NMR analyzes are in accordance with the expected product (brominated compound mixture and chlorinated compound).
  • the compound (2/2 ') is stirred at 100 ° C. for 22 hours in the presence of 0.45 g of compound (3) and 0.05 g of Kl in 15 ml of dimethylformamide.
  • the reaction medium is subsequently brought to room temperature and then poured into diisopropyl ether.
  • the residue obtained is washed with acetone and then solubilized with dichloromethane.
  • the residual insoluble matter is subsequently filtered.
  • the dye in solution in the dichloromethane is precipitated by addition of ethyl acetate. The dark purple precipitate is filtered, dried under vacuum and analyzed.
  • Compound 1 is a commercial compound
  • reaction medium is cooled to ambient temperature and then poured into ethyl acetate (500 ml).
  • the precipitate obtained is filtered and then washed several times with ethyl acetate and finally dried under vacuum. 44 g of a dark violet powder corresponding to compound 5 are obtained.
  • the analyzes are in accordance with the expected product.
  • Compound 6 is a commercial compound.
  • reaction medium is cooled to room temperature and then poured into ethyl acetate (200 ml).
  • the precipitate obtained is filtered and then washed several times with ethyl acetate and finally dried under vacuum. 4.5 g of a dark violet powder corresponding to compound 7 are obtained.
  • the analyzes are in accordance with the expected product.
  • reaction medium is cooled to room temperature and then poured into ethyl acetate (150 ml).
  • the precipitate obtained is filtered and then washed several times with ethyl acetate and finally dried under vacuum. 3 g of a bright orange powder corresponding to compound 8 are obtained.
  • the analyzes are in accordance with the expected product.
  • the analyzes are in accordance with the expected product.
  • 100 g of the above composition are applied to hair for 30 minutes at room temperature. Then rinse with water and dry the hair.
  • the hair is colored in red-purple.

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EP05825515A 2004-12-15 2005-12-15 Composes diazoiques dissymetriques, compositions les comprenant, procede de coloration et dispositif renfermant ces compositions Withdrawn EP1836193A1 (fr)

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US64697605P 2005-01-27 2005-01-27
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FR2925307B1 (fr) 2007-12-21 2009-12-18 Oreal Procede de coloration directe eclaircissante ou d'oxydation en presence d'une amine organique particuliere et dispositif
EP2198832B1 (fr) 2008-12-19 2017-01-25 L'Oréal Procédé d'éclaircissement de fibres kératiniques humaines mettant en oeuvre une composition anhydre et dispositif
EP2198843B1 (fr) 2008-12-19 2017-09-13 L'Oréal Eclaircissement de fibres kératiniques humaines mettant en oeuvre une composition anhydre comprenant un melange monoethanolamine / acide amine basique et dispositif
JP5815205B2 (ja) 2008-12-19 2015-11-17 ロレアル 有機アミン及び無機塩基の存在下で、淡色化し、あるいは淡色化直接染色し、あるいは酸化染色する方法、及びそのためのデバイス
FR2940104B1 (fr) 2008-12-19 2011-08-19 Oreal Procede de traitement des cheveux mettant en oeuvre une emulsion directe comprenant un agent oxydant et une composition contenant un agent alcalin
FR2940077B1 (fr) 2008-12-19 2012-07-20 Oreal Procede de coloration eclaircissante de matieres keratiniques mettant en oeuvre une composition anhydre colorante comprenant un agent alcalin et une composition oxydante.
US7927381B2 (en) 2008-12-19 2011-04-19 L'oreal S.A. Process for lightening or lightening direct dyeing or oxidation dyeing in the presence of an aqueous composition comprising at least one fatty substance, and device
US7947089B2 (en) 2008-12-19 2011-05-24 L'oreal S.A. Method of coloring or lightening in the presence of an inorganic base and kit
FR2940103B1 (fr) 2008-12-19 2011-06-10 Oreal Procede de coloration eclaircissante de matieres keratiniques mettant en oeuvre une emulsion comprenant un colorant et un agent alcalin et une composition oxydante
US7909888B2 (en) 2008-12-19 2011-03-22 L'oreal Process for dyeing or lightening human keratin fibers using an anhydrous composition and a monoethanolamine/basic amino acid mixture, and suitable device therefor
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KR20070086179A (ko) 2007-08-27
FR2879191B1 (fr) 2007-08-24
US20080168607A1 (en) 2008-07-17
WO2006063866A1 (fr) 2006-06-22
FR2879191A1 (fr) 2006-06-16
CN101124218A (zh) 2008-02-13
BRPI0517201A (pt) 2008-09-30
MX2007007182A (es) 2007-08-14

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