Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
  • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
  • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• • 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
  • A61K8/49—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
• • 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
  • 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
  • A61K8/4953—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 containing pyrimidine ring derivatives, e.g. minoxidil
• • 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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
  • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
  • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
  • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms

Definitions

• the subject of the invention is a composition for the oxidation dyeing of keratin fibers, and in particular human keratin fibers such as the hair, comprising at least one oxidation base and, as coupler, at least one 2- acylaminophenol of formula (I) comprising at least one cationic group Z of formula (II), their use as a coupler for the oxidation dyeing of keratin fibers, the oxidation dyeing processes using them, as well as new cationic 2-acylaminophenols of formula (I ').
• oxidation dye precursors in particular ortho or para-phenylenediamines, ortho or paraaminophenols, heterocyclic compounds such as diaminopyrazole derivatives, called generally oxidation bases.
• oxidation dye precursors in particular ortho or para-phenylenediamines, ortho or paraaminophenols, heterocyclic compounds such as diaminopyrazole derivatives, called generally oxidation bases.
• the precursors of oxidation dyes, or oxidation bases are colorless or weakly colored compounds which, associated with oxidizing products, can give rise, through an oxidative condensation process, to colored and coloring compounds.
• the dyes must also make it possible to cover white hair, and finally be the least selective possible, that is to say allow to obtain the smallest possible color differences throughout the same keratin fiber, which can be in differently sensitized effect (ie damaged) between its tip and its root.
• Paraphenylenediamines are generally used to obtain red shades, alone or in admixture with other bases, and in combination with appropriate couplers, 4-aminophenol, and to obtain blue shades.
• the first object of the invention is therefore a composition for the oxidation dyeing of keratin fibers, and in particular human keratin fibers such as the hair, characterized in that it contains, in a medium suitable for dyeing:
• R represents a hydrogen atom; a group Z as defined below; a radical comprising from 1 to 15 carbon atoms, linear or branched (the branch or branches may form one or more carbon rings comprising from 3 to 7 members), which may contain one or more double bonds and / or one or more triple bonds, (said double bonds optionally leading to aromatic groups), one or more carbon atoms of which can be replaced by an oxygen, nitrogen, or sulfur atom or by an SO 2 group, and whose carbon atoms may, independently of one another, be substituted by one or more halogen atoms; it being understood that said group SO 2 is not directly connected to the nitrogen atom in position 7 carrying the radical R ⁇ ; said radical R 1 not comprising a peroxide bond nor of diazo, nitro or nitroso radicals;
• R 2 represents a hydrogen atom; a group Z as defined below; a radical comprising from 1 to 20 carbon atoms, linear or branched (the branch or branches may form one or more carbon rings comprising from 3 to 7 members), which may contain one or more double bonds and / or one or more triple bonds ( said double bonds optionally leading to aromatic groups), and one or more carbon atoms of which can be replaced by an oxygen, nitrogen, or sulfur atom or by an SO 2 group, and whose carbon atoms can, independently of each other, be substituted by one or more halogen atoms; said R 2 radical not comprising a peroxide bond nor of diazo, nitro or nitroso radicals; and it being understood that R 2 cannot represent a hydroxyl or thio radical;
• R 3 , R 4 and R 5 identical or different, represent a hydrogen or halogen atom; a group Z as defined below; a radical comprising from 1 to 20 carbon atoms, linear or branched (the branch or branches may then form one or more rings having from 3 to 7 members), which may contain one or more double bonds and / or one or more triple bonds ( said double bonds possibly leading to aromatic groups), and one or more carbon atoms of which can be replaced by an oxygen, nitrogen, or sulfur atom or by an SO 2 group, and whose carbon atoms can , independently of one another, be substituted by one or more halogen atoms; said radicals R 3 , R 4 and R 5 not comprising a peroxide bond nor of diazo, nitro or nitroso radicals; and it being understood that
• R 5 cannot represent a hydroxyl, thio or amino radical or a substituted or unsubstituted sulfonylamino group; and it being understood that the radicals R 3 , R 4 and R 5 cannot be linked to the benzene ring of formula (I) by a -NH-NH- bond;
• Y represents a hydrogen or halogen atom; a group -ORg, -SR 6 or -NH-SO 2 R 6 in which R 6 represents an alkyl radical in C r C 6 , linear or branched (the branch or branches can then form one or more cycles comprising from 3 to 6 chain links), substituted or unsubstituted by one or more radicals chosen from the group consisting of a halogen atom, a hydroxy radical, C 4 -C 4 alkoxy, amino and CC 4 aminoalkyl; a phenyl radical substituted or unsubstituted by one or two radicals chosen from the group consisting of a C 4 -C 4 alkyl, trifluoromethyl, carboxy, CC 4 alkoxycarbonyl, halogen, hydroxy, C 1 -C 4 amino alkoxy radical, and C ⁇ O aminoalkyl; or a benzyl radical; and it being understood that Y cannot represent -NH-SO 2 R 6 when R 3 represents
• - B represents a radical comprising from 1 to 15 carbon atoms, linear or branched (the branch or branches can then form one or more rings comprising from 3 to 7 members), which can contain one or more double bonds and / or one or more triple bonds, said double bonds optionally leading to aromatic groups, and one or more carbon atoms of which can be replaced by an oxygen, nitrogen or sulfur atom or by an SO 2 radical; and of which one or more carbon atoms can, independently of each others, be substituted by one or more halogen atoms or by one or more Z groups; said radical B not comprising a peroxide bond or of diazo, nitro or nitroso radicals;
• radical B is linked to the group D by any one of the atoms of the radical D;
• - n and p can, independently of one another, take the value 0 or 1;
• Z 1 ( Z 2 , Z 3 , and Z 4 , independently of each other, represent an oxygen atom; a sulfur atom; a nitrogen atom substituted or unsubstituted by a radical R rent; or an atom carbon substituted or unsubstituted by one or two radicals R ⁇ , which are identical or different;
• - Z 5 represents a nitrogen atom; or a carbon atom substituted or unsubstituted by a radical R ⁇ ;
• Z 6 can take the same meanings as those indicated below for the radical R ⁇ , it being understood that Z 6 is different from a hydrogen atom;
• radicals Z 1 or Z 5 can, in addition, form with Z 6 a saturated or unsaturated ring comprising from 5 to 7 links, each link being substituted or unsubstituted by one or two identical or different radicals R;
• - R represents a hydrogen atom; a group Z; a radical comprising from 1 to 10 carbon atoms, linear or branched, which can contain one or more double bonds and / or one or more triple bonds, the said double bonds can then optionally lead to aromatic groups, and of which one or more atoms of carbon may be replaced by an oxygen, nitrogen, or sulfur atom, or by an SO 2 group, and one or more carbon atoms of which may, independently of one another, be substituted by one or more 'halogen; said radical not comprising a peroxide bond or diazo, nitro or nitroso radicals;
• two of the adjacent radicals Z ⁇ Z 2 , Z 3 , Z 4 and Z 5 may also form a ring comprising from 5 to 7 links, each link being independently represented by a carbon atom substituted or unsubstituted by one or two radicals R personallyIdentical or different; a nitrogen atom substituted or unsubstituted by a radical R ⁇ ; an oxygen atom; or a sulfur atom;
• radicals R 7 , R 8 , R 9 , and R 10 identical or different, have the same meanings as those indicated above for the radical R réelle;
• the radicals R 7 , R 8 and R 9 can also form, two by two with the quaternary nitrogen atom to which they are attached, one or more saturated rings comprising from 5 to 7 links, each link being independently represented by an atom carbon substituted or unsubstituted by one or two identical or different radicals R; a nitrogen atom substituted or unsubstituted by a radical R seemingly; an oxygen atom; or a sulfur atom;
• - X represents an organic or inorganic anion and is preferably chosen from the group consisting of a halide group such as chloride, bromide, fluoride, iodide; a hydroxide; a sulphate; a hydrogen sulphate; an alkyl (CC 6 ) sulphate such as for example a methylsulfate or an ethylsulfate; an acetate; a tartrate; an oxalate; a (C 1 -C 6 ) alkyl sulfonate such as methylsulfonate; an arylsulfonate substituted or unsubstituted by a CC 4 alkyl radical such as for example a
• the oxidation dye composition containing the compound or compounds of formula (I) according to the invention makes it possible to obtain powerful colorings in shades ranging from red to blue and moreover having remarkable tenacity for the various treatments that keratin fibers can undergo. These properties are particularly remarkable in particular with regard to the resistance of the colorings obtained with respect to the action of light, bad weather, washing, permanent waving and perspiration.
• R ⁇ preferably denotes a hydrogen atom, a radical Z; a group A. ,, A 2 , A 3 , A 4 or A 5 , optionally separated from the nitrogen located in position 7 on which the radical R ⁇ is fixed by a group - (CO) -.
• group A is intended to mean a C r C 8 alkyl radical, linear or branched, which may bear one or two double bonds or a triple bond, be substituted or unsubstituted by a group chosen from a group A 2 , A 4 , and A 5 , be substituted or unsubstituted by one or two groups, identical or different, chosen from N-alkyl (C 1 -C 3 ) amino, N-alkyl (C 1 -C 3 ) groups - N-alkyl (C 1 -C 3 ) amino, alkoxy (C 1 -C 6 ), oxo, alkoxycarbonyl, acyloxy, amide, acylamino, ureyl, sulfoxy, sulfonyl, sulfonamido, sulfonylamino, bromo, cyano, carboxy, and be substituted or unsubstituted by one or more hydroxyl
• group A 2 is intended to mean an aromatic group of phenyl or naphthyl type, which may be substituted or unsubstituted by one to three groups, identical or different, chosen from the methyl, trifluoromethyl, ethyl, isopropyl, butyl, pentyl, fluoro groups, chloro, bromo, methoxy, trifluoromethoxy, ethoxy, propyloxy, acetyloxy, acetyl, and cyano.
• group A 3 is intended to mean heteroaromatic groups chosen from the furanyl, thiophenyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, isoxazolyl, isothiazolyl, pyrazolyl, pyrazoltriazolyl groups.
• pyrazoloimidazolyle pyrrolotriazolyle, pyrazolopyrimidyle, pyrazolopyridyle, pyridyle, pyrimidyle, benzoimidazolyle, benzoxazolyle, benzothiazolyle, indolyle, indolidinyle, isoindolyle, indazolyle, benzotriazolyle, benzotriazolyle, quinolinyl, benzoimid, benolinimides C alkyl
• group A 4 is intended to mean a C 3 -C 7 cycloalkyl radical, a norbornanyl radical, whether or not bearing a double bond and substituted or unsubstituted by 1 or 2 radicals chosen from C 1 O 4 alkyl radicals, linear or branched, monohydroxyalkyl in CC 4 , polyhydroxyalkyl in C 2 -C 4 , carboxy, alkoxycarbonyl, halogen, amido, amino and hydroxy.
• group A 5 is intended to mean a heterocycle chosen from the dihydrofuranyl, tetrahydrofuranyl, butyrolact-one-yl, dihydrothiophenyl, tetrahydrothiophenyl, tetrahydrothiophen-one-yl, iminothiolane, dihydropyrrolyl, yyridolidone, pyrrolidinyl, pyrrolidinyl rings.
• R ⁇ preferably represents a hydrogen atom; a methyl, ethyl, isopropyl, allyl, phenyl, benzyl, fluorobenzyl, hydroxybenzyl, difluorobenzyl, trifluorobenzyl, chlorobenzyl, bromobenzyl, methoxybenzyl, dimethoxybenzyl, (trifluoromethoxy) benzyl, 3,4-methylendioxyethyl, 4-chlorobenzyl, 3-chlorobenzyl radical,
• R ⁇ represents a hydrogen atom or a methyl radical.
• R 2 preferably denotes a hydrogen atom, an amino group; a group Z; a group A ⁇ A 2 , A 3 , A 4 or A 5 as defined above, optionally separated from the carbon (in position 8) of the amide function of the compound of formula (I) by a group -O-, - NH, -Nalkyl (CyC 3 ) -, - (CO) -, - (CO) O- or - (CO) NH-.
• R 2 preferably denotes a group Z; a radical chosen from the group (G1) consisting of a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl radical; cyclopropyl, cyclobutyl, cyclopentyl, cyclopentylmethyl,, 3-cyclopentyl-propyl, cyclohexyl, 2-cyclohexyl-ethyl, norbomane-2-yl, vinyl, 1-methylvinyl, 2-methylvinyl, 2,2-dimethylvinyl, allyl, 3-butenyl ; phenyl, methylphenyl, dimethylphenyl, 2,4,6-trimethylphenyl, 4-ethylphenyl, (trifluoromethyl) phenyl, hydroxyphenyl
• said ring is preferably chosen from the groups 2-pyrrolidinon-1-yl, methyl-2-pyrrolidinon-1-yl, 5-carboxy-2-pyrrolidinon-1-yl, 5-methoxycarbonyl-2-pyrrolidinone-1-yl, pyrazolinone-1-yl, succinimide-1-yl, 3,5-diketopyrazolidin-1-yl, oxindolin-1-yl, maleimide-1yl, isoindole-1, 3- dione-2-yl, 2-piperidinone-1-yl, and glutarimide-1-yl.
• R 2 represents a radical chosen from the group (G2) consisting of a methyl, ethyl, propyl, allyl, phenyl, tetrahydrofuran-2-yl, furan-2-yl, thiophene-2-yl radical, pyridinyl, piperazin-2-yl, fluoro methyl, chloromethyl, 2-chloroethyl, methoxymethyl, acetoxymethyl, 1, 2-dihydroxyethyl, methoxycarbonyl, 2-carboxyethyl, methoxy, ethoxy, propoxy, allyloxy, 2-chloroethoxy, 2-chloroethoxy , ethylamino, allylamino, 2-chloroethylamino, pyridylamino, dimethylamino, 1-pyrolidinyl, and 4-morpholinyl; or a group -D ⁇ -ED ⁇ -OED ⁇
• R 3 and R 4 identical or different, preferably denote a hydrogen or halogen atom; a hydroxyl or amino group; a group Z; a group A ,, A 4 , or A 5 as defined above; a group A 1 t A 2 , A 3 , A 4 or A 5 as defined above and separated from the phenolic nucleus of formula (I) by an oxygen atom or by a group -NH-, -Nalkyl (C r C 3 ) -, -O (
• R 3 even more preferably represents a hydrogen or chlorine atom; a group Z; a methyl, hydroxy methyl, methoxymethyl, 1-hydroxyethyl, aminomethyl, methylaminomethyl, hydroxy, methoxy, acetoxy, amino, methylamino, or 2-hydroxyethylamino radical; a group -NH (CO) R 12 in which R 12 represents one of the radicals listed in the group (G1) as defined above; a group -NHSO 2 R 13 , in which R 13 represents one of the radicals listed in the group (G3) consisting of the methyl, trifluoromethyl, ethyl, 2-chloroethyl, propyl, 3-chloropropyl, isopropyl, butyl, thiophene-2 radicals -yl, hydroxy, ethoxy and dimethylamino.
• a group Z a methyl, hydroxy methyl, methoxymethyl, 1-hydroxyethyl, aminomethyl, methyl
• R ⁇ and R 3 form a ring, together with the nitrogen atom in position 7 of the compound of formula (I), it is preferred for -R., R 3 - the bond -CH 2 CH 2 CH 2 -.
• R 2 and R 3 form a ring together with the nitrogen atom in position 7 of the compound of formula (I), it is preferred for R 2 -R 3 - the bonds -CH 2 -, -C (CH 3 ) 2 -, or -CH 2 CH 2 -.
• R 3 represents a hydrogen atom; a methyl, hydroxymethyl, aminomethyl, hydroxy, methoxy, amino, methylamino radical; a methanesulfonylamino group; ethanesulfonylamino; dimethylamino-sulfonylamino; a group -NH (CO) R 14 in which R 14 represents one of the radicals listed in the group (G2) as defined above; or a group -OED 2 , -NH-ED 2 , -CH 2 OED 2 , -CH 2 NH-ED 2 , -CH 2 NH (CO) -D 2 , -NH (CO) -D 2 , -NH ( CO) -ED 2> -NH (CO) OED 2 , -NH (CO) NH-ED 2 , or -NH (SO 2 ) -ED 2 , in which -E- has the same meaning as that indicated above and D 2 represents a group D
• R 4 preferably represents a hydrogen or chlorine atom; a group Z; a methyl, ethyl, hydroxymethyl, methoxymethyl, aminomethyl, methylaminomethyl, hydroxy, methoxy, acetoxy, amino, methylamino, N-piperidino, or N-morpholino radical; a group -NH (CO) R 15 in which R 15 represents one of the radicals listed in the group (G1) defined above; or a group -NHSO 2 R 16 in which R 16 represents one of the radicals listed in the group (G3) defined above.
• R 4 represents a hydrogen or chlorine atom; a methyl, hydroxymethyl, aminomethyl, hydroxy, methoxy, amino, or methylamino radical; a methanesulfonylamino group; ethanesulfonylamino; dimethylaminosulfonylamino; a group -NH (CO) R 17 in which R 17 represents one of the radicals listed in the group (G2) defined above; or a group -OED 3 , -NH-ED 3 , -CH 2 OED 3 , -CH 2 NH-ED 3 , -CH 2 NH (CO) -D 3 , -NH (CO) -D 3 , -NH ( CO) -ED 3 , -NH (CO) OED 3 , -NH (CO) NH-ED 3 , or -NH (SO 2 ) -ED 3 , in which -E- has the same meaning as that indicated above , and D 3 represents a
• R 5 preferably represents a hydrogen, chlorine, fluorine or bromine atom; a group Z; a methyl, trifluoromethyl, allyl, hydroxymethyl, methoxymethyl, 1-hydroxyethyl, aminomethyl, methylaminomethyl, methoxy, acetoxy, or methylamino radical; or a group -NH (CO) R 18 in which R 18 represents one of the radicals listed in the group (G1) defined above.
• R 5 represents a hydrogen, chlorine or fluorine atom; a methyl, hydroxymethyl, aminomethyl, methoxy, or methylamino radical; a group -NH (CO) R 19 in which R 19 represents one of the radicals listed in the group (G2) defined above; or a group -OED 4 , -NH-ED 4 , -CH 2 OED 4 , -CH 2 NH-ED 4 , -CH 2 NH (CO) -D 4 , -NH (CO) -D 4 , -NH (CO) -D 4 , -NH ( CO) -ED 4 , -NH (CO) OED 4 ,
• Y is preferably chosen from a hydrogen, chlorine, fluorine or bromine atom; a methoxy, ethoxy, propoxy, benzyloxy, phenoxy, -OCH 2 CH 2 OCH 3 group ; -OCH 2 CH 2 OCH 3 ; -OCH 2 CH 2 N (CH 3 ) 2 ; -OCH 2 (CO) OH, -OCH 2 (CO) OCH 3 , -OCH 2 (CO) OC 2 H 5 , -SCH 2 CH 2 CO 2 H, or -NHSO 2 CH 3 ; it being understood that Y cannot represent a group -NHSO 2 CH 3 when R 3 represents a hydroxyl radical.
• Y represents a hydrogen or chlorine atom, a methoxy group, -OCH 2 (CO) OH, or -OCH 2 (CO) OCH 3 .
• the groups D there may be mentioned, by way of example, the groups imidazolinium, thiazolinium, oxazolinium, pyrrolinium, 1, 2,3-triazolinium, 1, 2,4-triazolinium, isoxazolinium, ixothiazolinium, imidazolidinium, thiazolidinium, pyrazolinium , pyrazolidinium, oxazolidinium, pyrazolthazolinium, pyrazoloimidazolinium, pyrrolotriazolinium, pyrazolopyrimidinium, pyrazolopyridinium, pyridinium, pyrimidinium, pyrazinium, triazinium, benzoimidazolinium, benzoxazolinium, benzothiazolinium, ind
• D represents a 3-methylimidazolidinium-1-yl, 3- (2-hydroxyethyl) imidazolidinium-1-yl group,
• R T represents a hydrogen atom
• - R 2 represents a group -D. ,, -ED ⁇ -OED ⁇ -NH-ED T , as defined above; or a radical chosen from the group (G4) consisting of a methyl, methoxymethyl, 2-carboxyethyl, methoxy, amino, ethylamino, 1-pyrolidinyl radical; - R 3 represents a hydroxy, amino or methylamino radical; a group -NH (CO) R 20 in which R 20 represents one of the radicals listed in the group (G4) defined above; a methanesulfonylamino, ethanesulfonyiamino, or dimethylaminosulfonylamino group; a group -OED 2 , -NH-ED 2) -NH (CO) -D 2 , -NH (CO) -ED 2 , -NH (CO) OED 2 ,
• R 4 represents a hydrogen or chlorine atom, or a methyl group
• R 5 represents a hydrogen, chlorine or fluorine atom, or a methyl group
• - Y represents a hydrogen or chlorine atom; a methoxy group, or -OCH 2 (CO) OCH 3 ; it being understood that at least one of the groups R 2 and R 3 contains a group Z;
• R T represents a hydrogen atom
• - R 2 represents a group -D. ,, -ED ⁇ -OED ,, or -NH-ED ⁇ as defined above; or one of the radicals listed in the group (G4) defined above;
• - R 3 represents a hydrogen atom; or a methyl radical
• - R 4 represents a hydroxy, amino, methylamino, methanesulfonylamino, ethanesulfonyiamino, or dimethylaminosulfonylamino radical
• R 5 represents a hydrogen, chlorine or fluorine atom; or a methyl, methoxy, or methylamino group
• - Y represents a hydrogen or chlorine atom; a methoxy group, or -OCH 2 (CO) OCH 3 ; it being understood that at least one of the groups R 2 and R 4 contains a group Z; iii) - R 1 represents a hydrogen atom;
• - R 2 represents one of the radicals listed in the group (G4) defined above; or a group -D. ,, -ED. ,, -OED. ,, -NH-ED T , as defined above; - R 3 represents a hydrogen atom; or a methyl radical;
• R 4 represents a hydrogen or chlorine atom; a methyl radical; or a methoxy, or methylamino group;
• R 5 represents a group -NH (CO) R 22 in which R 22 represents one of the radicals listed in the group (G4) defined above; or a group -OED 4 , -NH-ED 4 , -NH (CO) -D 4 , -NH (CO) -ED 4 , -NH (CO) OED 4 , or
• - Y represents a hydrogen or chlorine atom; or a methoxy group, or -OCH 2 (CO) OCH 3 ; it being understood that at least one of the groups R 2 and R 5 contains a group Z;
• R 2 represents a group -D ⁇ -ED ⁇ -OED ! , or -NH-ED ⁇ as defined above;
• - R 3 represents a hydrogen atom; or a methyl radical
• - R 4 represents a hydrogen or chlorine atom; or a methyl radical
• R 5 represents a hydrogen, chlorine or fluorine atom; or a methyl group
• - Y represents a hydrogen atom, or chlorine; or a methoxy group, or -OCH 2 (CO) OCH 3 .
• the compound (s) of formula (I) in accordance with the invention and / or the acid addition salt (s) thereof preferably represent from 0.0005 to 12% by weight approximately of the total weight of the dye composition, and even more preferably from 0.005 to 6% by weight approximately of this weight.
• oxidation base or bases which can be used in the dye composition in accordance with the invention is not critical. They are preferably chosen from the oxidation bases conventionally used in oxidation dyeing and among which mention may especially be made of paraphenylenediamines, bis-phenylalkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases.
• paraphenylenediamines mention may more particularly be made, for example, of paraphenylenediamine, paratoluylenediamine, 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, 4-N, N-bis- ( ⁇ -hydroxyethyl) amino 2-chloro aniline , 2- ⁇ -hydroxyethyl para
• paraphenylenediamines mentioned above very particularly preferred are 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 paraphenylenediamine, 2- ⁇ -acetylaminoethyloxy paraphenylenediamine, and their addition salts with an acid.
• para-aminophenol mention may more particularly be made, for example, of 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, 4-amino 2-fluoro phenol, and their addition salts with an acid.
• 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, 4-amino 2-fluoro phenol, and their addition salts with an
• ortho-aminophenols there may be mentioned more particularly by way of example, 2-amino phenol, 2-amino 5-methyl phenol, 2-amino 6-methyl phenol, 5-acetamido 2-amino phenol, and their addition salts with an acid.
• heterocyclic bases that may be mentioned more particularly by way of example, pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
• pyridine derivatives mention may more particularly be made of the compounds described, for example, in 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 mention may be made more particularly of the compounds described for example in German patents DE 2,359,399 or Japanese patents JP 88-169,571 and JP 91-10659 or 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-diaminopyhmidine, 2,5,6 -triaminopyrimidine, and pyrazolo-pyrimidine 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] -pyhmidine-3,7-diamine; 2,5-dimethyl pyrazolo- [1,5-a] -pyrimidine-3,7-diamine; pyrazolo- [1,5-a] -pyrimidine-3
• dye compositions containing one or more paraphenylenediamines and / or one or more heterocyclic oxidation bases are particularly preferred.
• the oxidation base (s) preferably represent from 0.0005 to 12% by weight approximately of the total weight of the dye composition, and even more preferably from 0.005 to 6% by weight approximately of this weight.
• the dye composition according to the invention may also contain, in addition to the compound or compounds of formula (I) above, one or more additional couplers which can be chosen from the couplers conventionally used in oxidation dyeing and among which mention may in particular be made of metaphenylenediamines, meta-aminophenols, metadiphenols and heterocyclic couplers such as, for example, indole derivatives, indoline derivatives, pyridine derivatives and pyrazolones, and their addition salts with an acid.
• additional couplers which can be chosen from the couplers conventionally used in oxidation dyeing and among which mention may in particular be made of metaphenylenediamines, meta-aminophenols, metadiphenols and heterocyclic couplers such as, for example, indole derivatives, indoline derivatives, pyridine derivatives and pyrazolones, and their addition salts with an acid.
• couplers are more particularly chosen from 2-methyl 5-amino phenol, 5-N- ( ⁇ -hydroxyethyl) amino 2-methyl phenol, 3-amino phenol, 1, 3-di hydroxy benzene, 1, 3-dihydroxy 2-methyl benzene, 4-chloro 1, 3-dihydroxy benzene, 2,4-diamino l- ( ⁇ -hydroxyethyloxy) benzene, 2-amino 4- ( ⁇ -hydroxyethylamino) 1-methoxy benzene, 1,3-diamino benzene, 1,3-bis- (2,4-diaminophenoxy) propane, sesamol, ⁇ -naphthol, 6-hydroxy indole, 4-hydroxy indole, 4-hydroxy N -methyl indole, 6-hydroxy indoline, 2,6-dihydroxy 4-methyl pyridine, 1-H 3-methyl pyrazole 5-one, 1-phenyl 3-methyl pyrazole 5-one, and their salts addition with an acid.
• these additional couplers preferably represent from 0.0001 to 10% by weight approximately of the total weight of the dye composition and even more preferably from 0.005 to 5% by weight approximately of this weight.
• addition salts with an acid which can be used in the context of the dye compositions of the invention are in particular chosen from hydrochlorides, hydrobromides , sulfates, citrates, succinates, tartrates, lactates and acetates.
• the medium suitable for dyeing generally consists of water or of a mixture of water and at least one organic solvent to dissolve the compounds which are not sufficiently soluble in water.
• organic solvent mention may, for example, be made of lower CC 4 alkanols, such as ethanol and isopropanol; glycerol; glycols and glycol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, monoethyl ether and diethylene glycol monomethyl ether, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, analogous products and mixtures thereof.
• the solvents may be present in proportions preferably of between 1 and 40% by weight approximately relative to the total weight of the dye composition, and even more preferably between 5 and 30% by weight approximately.
• 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 basifying agents usually used in dyeing keratin fibers.
• acidifying agents there may be mentioned, by way of example, mineral or organic acids such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid, sulfonic 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, sulfonic acids.
• basifying agents there may be mentioned, by way of example, ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamines as well as their derivatives, sodium or potassium hydroxides and compounds of following formula (V):
• R24 R26 in which W is a propylene residue substituted or unsubstituted by a hydroxyl group or a CC 6 alkyl radical;
• R 23 , R 24 , R 25 and R 26 identical or different, represent a hydrogen atom, an alkyl radical in CC 6 OR hydroxyalkyl in CC 6 .
• the oxidation dye compositions in accordance with the invention may also contain at least one direct dye, in particular for modifying the shades or enriching them with reflections.
• the dye composition in accordance with the invention may also contain various adjuvants conventionally used in compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or mixtures thereof, anionic polymers, cationic, non-ionic, amphoteric, zwitterionic or mixtures thereof, mineral or organic thickening agents, antioxidant agents, penetration agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as by example of volatile or non-volatile silicones, modified or unmodified, film-forming agents, ceramides, preserving agents, opacifying agents.
• the dye composition according to the invention can be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratin fibers, and in particular human hair.
• the subject of the invention is also a process for the oxidation dyeing of keratin fibers and in particular human keratin fibers such as the hair using the dye composition as defined above.
• At least one dye composition as defined above is applied to the fibers, the color being revealed at acidic, neutral or alkaline pH using an oxidizing agent which is added just at the time of use in the dye composition or which is present in an oxidizing composition applied simultaneously or sequentially.
• the dye composition described above is preferably mixed with an oxidizing composition containing, in a suitable medium for dyeing, at the time of use. at least one oxidizing agent present in an amount sufficient to develop coloring.
• the mixture obtained is then applied to the keratin fibers and left to stand for 3 to 50 minutes approximately, preferably 5 to 30 minutes approximately, after which it is rinsed, washed with shampoo, rinsed again and dried.
• the oxidizing agent can be chosen from the oxidizing agents conventionally used for the oxidation dyeing of keratin fibers, and among which mention may be made of hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as as perborates and persulfates, and enzymes such as peroxidases, laccases, tyrosynases and oxidoreductases among which there may be mentioned in particular pyranose oxidases, glucose oxidases, glycerol oxidases, lactate oxidases, pyruvate oxidases , and uricases.
• the pH of the oxidizing composition containing the oxidizing agent as defined above is such that after mixing with the dye composition, the pH of the resulting composition applied to the keratin fibers preferably varies between 3 and 12 approximately, and again more preferably between 5 and 11. It is adjusted to the desired value by means of acidifying or basifying agents usually used in dyeing keratin fibers and as defined above.
• the oxidizing composition as defined above may also contain various adjuvants conventionally used in compositions for dyeing the hair and as defined above.
• composition which is finally applied to the keratin fibers can be in various forms, such as in the form of liquids, creams, gels, or in any other form suitable for dyeing keratin fibers, and in particular human hair. .
• Another object of the invention is a device with several compartments or "kit” for dyeing or any other packaging system with several compartments, a first compartment of which contains the dye composition as defined above and a second compartment of which contains the oxidizing composition. as defined above.
• These devices can be equipped with a means enabling the desired mixture to be delivered to the hair, such as the devices described in patent FR-2,586,913 in the name of the applicant.
• R ⁇ , R ' 2 , R' 3 , R ' 4 , R' 5 and Y can take the same meanings as those indicated above for R ⁇ R 2 , R 3 , R 4 , R 5 and Y, in which at least one of the groups R to R ' 5 represents a group Z' which can take the same meanings as those indicated above for the group Z; excluding the following compounds:
• R represents a radical é feel 4-m e thyl-C 6 H 4, 4-chloro-C 6 H 4 or 2-ethoxy-C 6 H 4
• the addition salts with an acid of the compounds of formula (I ') can in particular be chosen from hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates and acetates.
• the invention finally relates to the use of the compounds of formula (I ") as a coupler for the oxidation dyeing of keratin fibers and in particular human keratin fibers such as the hair.
• each weight-for-weight composition was mixed weight for weight with a 20 volume hydrogen peroxide solution (6% by weight) of pH 3.
• the mixture obtained was applied to locks of permanent gray hair containing 90% white hairs for 30 minutes.
• the locks were then rinsed, washed with a standard shampoo, rinsed again and then dried.
• the mixture obtained was applied to locks of permanent gray hair containing 90% white hairs for 30 minutes.
• the locks were then rinsed, washed with a standard shampoo, rinsed again and then dried.

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• 1999
  • 1999-01-21 FR FR9900638A patent/FR2788691B1/fr not_active Expired - Fee Related
• 2000
  • 2000-01-20 DE DE60006036T patent/DE60006036T2/de not_active Expired - Lifetime
  • 2000-01-20 AU AU30571/00A patent/AU3057100A/en not_active Abandoned
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