U.S. patent application number 09/320286 was filed with the patent office on 2002-01-24 for composition for the oxidation dyeing of keratin fibres and dyeing process using this composition.
This patent application is currently assigned to L' Oreal S.A.. Invention is credited to COTTERET, JEAN, LANG, GERARD.
Application Number | 20020007522 09/320286 |
Document ID | / |
Family ID | 9526711 |
Filed Date | 2002-01-24 |
United States Patent
Application |
20020007522 |
Kind Code |
A1 |
LANG, GERARD ; et
al. |
January 24, 2002 |
COMPOSITION FOR THE OXIDATION DYEING OF KERATIN FIBRES AND DYEING
PROCESS USING THIS COMPOSITION
Abstract
The invention relates to a composition for the oxidation dyeing
of keratin fibers, and in particular human keratin fibers such as
the hair, having, in a medium suitable for dyeing, at least one
oxidation base and at least one specific cationic dye as direct
dye, as well as to the dyeing process using this composition.
Inventors: |
LANG, GERARD; (SAINT PRIX,
FR) ; COTTERET, JEAN; (SUR SEINE, FR) |
Correspondence
Address: |
THOMAS L IRVING
FINNEGAN HENDERSON FARABOW GARRETT
& DUNNER LLP
1300 I STREET NW
WASHINGTON
DC
200053315
|
Assignee: |
L' Oreal S.A.
|
Family ID: |
9526711 |
Appl. No.: |
09/320286 |
Filed: |
May 26, 1999 |
Current U.S.
Class: |
8/405 ; 8/406;
8/407 |
Current CPC
Class: |
A61K 8/4926 20130101;
A61Q 5/065 20130101; A61K 8/494 20130101; A61K 8/49 20130101 |
Class at
Publication: |
8/405 ; 8/406;
8/407 |
International
Class: |
A61K 007/13 |
Foreign Application Data
Date |
Code |
Application Number |
May 26, 1998 |
FR |
98-06604 |
Claims
What is claimed is:
1. A composition for the oxidation dyeing of keratin fibres
comprising: at least one oxidation base, at least one cationic
direct dye of formula (I) below: A--N.dbd.N--B (I) wherein: A is
chosen from structures A1, A2, and A3 below: 67wherein in said
structures A1 to A3: R.sub.1 is chosen from C.sub.1-C.sub.4 alkyl
radicals, a phenyl radical, and phenyl radicals having a
substituent chosen from C.sub.1-C.sub.4 alkyl radicals and halogen
atoms chosen from chlorine, bromine, iodine and fluorine; R.sub.2
is chosen from C.sub.1-C.sub.4 alkyl radicals and a phenyl radical;
R.sub.3 and R.sub.4, which may be identical or different, are
chosen from C.sub.1-C.sub.4 alkyl radicals and a phenyl radical or
together form a benzene ring having at least one substituent chosen
from C.sub.1-C.sub.4 alkyl radicals, C.sub.1-C.sub.4 alkoxy
radicals, and nitro radicals; R.sub.3 can also be a hydrogen atom;
R.sub.5 and R.sub.6, which may be identical or different, are
chosen from C.sub.1-C.sub.4 alkyl radicals and a phenyl radical or
together form a benzene ring which is unsubstituted or has at least
one substituent chosen from C.sub.1-C.sub.4 alkyl radicals,
C.sub.1-C.sub.4 alkoxy radicals, and nitro radicals; R.sub.5 can
also be a hydrogen atom; R.sub.7 and R.sub.8, which may be
identical or different, are chosen from a hydrogen atom, halogen
atoms chosen from chlorine, bromine, iodine and fluorine,
C.sub.1-C.sub.4 alkyl radicals, C.sub.1-C.sub.4 alkoxy radicals and
nitro radicals; Z is chosen from an oxygen atom, a sulphur atom,
and a group NR.sub.2, wherein R.sub.2 is chosen from
C.sub.1-C.sub.4 alkyl radicals and a phenyl radical; the ring
member L is chosen from --CH, --CR and
--N.sup.+R.sub.9(X.sup.-).sub.r; the ring member M is chosen from
--CH, --CR and --N.sup.+R.sub.9(X.sup.-).sub.r; r is an integer
equal to 0 or 1; R is chosen from C.sub.1-C.sub.4 alkyl radicals;
R.sub.9 is chosen from an atom O.sup.-, C.sub.1-C.sub.4 alkyl
radicals, and C.sub.1-C.sub.4 alkoxy radicals; X.sup.- is chosen
from an anion; with the provisos that: in said formula A3, at least
one of the ring members L and M is a group
--N.sup.+R.sub.9(X.sup.-).sub.r; when R.sub.6 is a C.sub.1-C.sub.4
alkyl radical and Z is a sulphur atom, then R.sub.5 is other than a
C.sub.1-C.sub.4 alkyl radical; when R.sub.6 is a C.sub.1-C.sub.4
alkyl radical and Z is a sulphur atom and when one of the radicals
R.sub.10 and R.sub.11 is a hydrogen atom, then R.sub.5 is other
than a hydrogen atom; when R.sub.9 is O.sup.-, then r=0; when L or
M is a radical --N.sup.+R.sub.9(X.sup.-).sub.r wherein R.sub.9 is a
C.sub.1-C.sub.4 alkyl radical and r=1, then at least one of the
radicals R.sub.7 and R.sub.8 is other than a hydrogen atom; when L
is a radical --N.sup.+R.sub.9(X.sup.-).sub.r, then M is chosen from
--CH and CR; when M is a radical --N.sup.+R.sub.9(X.sup.-).sub.r,
then L is chosen from --CH and CR; when Z is a group NR.sub.2
wherein R.sub.2 is a C.sub.1-C.sub.4 alkyl radical, then at least
one of the radicals R.sub.1, R.sub.5 and R.sub.6 is other than a
C.sub.1-C.sub.4 alkyl radical; when Z is a sulphur atom and R.sub.1
is a C.sub.1-C.sub.4 alkyl radical and when one of the radicals
R.sub.10 and R.sub.11 is a hydrogen atom, then R.sub.5 and R.sub.6
cannot together form an unsubstituted benzene ring; B is chosen
from: (a) a group of structure B1 below: 68wherein in structure B1,
R.sub.10 is chosen from a hydrogen atom, halogen atoms chosen from
chlorine, bromine, iodine and fluorine, C.sub.1-C.sub.4 alkyl
radicals, C.sub.1-C.sub.4 alkoxy radicals, a hydroxyl radical,
--NHR.sub.13 groups, --NR.sub.14R.sub.15groups,
--NHCO(C.sub.1-C.sub.4)al- kyl groups and a nitro, or forms with
R.sub.1, a 5- or 6-membered carbon ring or a ring containing at
least one hetero atom chosen from nitrogen, oxygen and sulphur;
R.sub.11 is chosen from a hydrogen atom, halogen atoms chosen from
chlorine, bromine, iodine and fluorine, C.sub.1-C.sub.4 alkyl
radicals, and C.sub.1-C.sub.4 alkoxy radicals or forms with
R.sub.12 or R.sub.13 a 5- or 6-membered carbon ring or a ring
containing at least one hetero atom chosen from nitrogen, oxygen
and sulphur; R.sub.12 is chosen from a hydrogen atom, a hydroxyl
radical, --NHR.sub.13 radicals, and --NR.sub.14R.sub.15 radicals;
R.sub.13 is chosen from a hydrogen atom, C.sub.1-C.sub.4 alkyl
radicals, C.sub.1-C.sub.4 monohydroxyalkyl radicals,
C.sub.2-C.sub.4 polyhydroxyalkyl radicals, and a phenyl radical;
R.sub.14 and R.sub.15, which may be identical or different, are
chosen from C.sub.1-C.sub.4 alkyl radicals, C.sub.1-C.sub.4
monohydroxyalkyl radicals, and C.sub.2-C.sub.4 polyhydroxyalkyl
radicals;; and (b) a 5- or 6-membered nitrogenous heterocyclic
group, a 5- or 6-membered nitrogenous heterocyclic group comprising
at least one additional hetero atom chosen from oxygen and sulphur
and/or at least one carbonyl group, wherein said heterocycles are
unsubstituted or have at least one substituent chosen from
C.sub.1-C.sub.4 alkyl, amino and phenyl radicals.
2. A composition according to claim 1, wherein said keratin fibres
are human keratin fibres.
3. A composition according to claim 2, wherein said human keratin
fibres are human hair.
4. A composition according to claim 1, having a pH ranging from 3
to 12.
5. A composition according to claim 1, having a pH ranging from
about 3 to about 12.
6. A composition according to claim 5, wherein said pH ranges from
about 5 to about 11.
7. A composition according to claim 1, wherein said anion X.sup.-
is chosen from chloride, methyl sulphate, ethyl sulphate, acetate,
and perchlorate.
8. A composition according to claim 1, wherein in said B, said 5-
or 6-membered nitrogenous heterocyclic group is a group of
structure B2 below: 69wherein structure B2: R.sub.16 and R.sub.17
are identical or different and are chosen from a hydrogen atom,
C.sub.1-C.sub.4 alkyl radicals and a phenyl radical; Y is chosen
from a group 70and n is an integer equal to 0 or 1.
9. A composition according to claim 1, wherein said at least one
oxidation base is chosen from para-phenylenediamines, double bases,
para-aminophenols, ortho-aminophenols, and heterocyclic oxidation
bases.
10. A composition according to claim 9, wherein said
para-phenylenediamines are chosen from compounds of formula (II)
below and acid addition salts thereof: 71wherein: R.sub.18 is
chosen from a hydrogen atom, C.sub.1-C.sub.4 alkyl radicals,
C.sub.1-C.sub.4 monohydroxyalkyl radicals, C.sub.2-C.sub.4
polyhydroxyalkyl radicals,
(C.sub.1-C.sub.4)alkoxy(C.sub.1-C.sub.4)alkyl radicals,
C.sub.1-C.sub.4 alkyl radicals substituted with an entity chosen
from nitrogenous groups, a phenyl group and a 4'-aminophenyl group;
R.sub.19 is chosen from a hydrogen atom, C.sub.1-C.sub.4 alkyl
radicals, C.sub.1-C.sub.4 monohydroxyalkyl radicals,
C.sub.2-C.sub.4 polyhydroxyalkyl radicals,
(C.sub.1-C.sub.4)alkoxy(C.sub.1-C.sub.4)alkyl radicals and
C.sub.1-C.sub.4 alkyl radicals substituted with a nitrogenous
group; R.sub.20 is chosen from a hydrogen atom, halogen atoms,
C.sub.1-C.sub.4 alkyl radicals, C.sub.1-C.sub.4 monohydroxyalkyl
radicals, C.sub.1-C.sub.4 hydroxyalkoxy radicals,
acetylamino(C.sub.1-C.sub.4)alkox- y radicals, C.sub.1-C.sub.4
mesylaminoalkoxy radicals and carbamoylamino(C.sub.1-C.sub.4)alkoxy
radicals, R.sub.21 is chosen from hydrogen and halogen atoms and
C.sub.1-C.sub.4 alkyl radicals.
11. A composition according to claim 10, wherein said halogen atoms
are chosen from chlorine, bromine, iodine, and fluorine atoms.
12. A composition according to claim 10, wherein said
para-phenylenediamines of formula (II) are chosen from
para-phenylenediamine, para-tolylenediamine,
2-chloro-para-phenylenediami- ne,
2,3-dimethyl-para-phenylenediamine,
2,6-dimethyl-para-phenylenediamine- ,
2,6-diethyl-para-phenylenediamine,
2,5-dimethyl-para-phenylenediamine,
N,N-dimethyl-para-phenylenediamine,
N,N-diethyl-para-phenylenediamine,
N,N-dipropyl-para-phenylenediamine,
4-amino-N,N-diethyl-3-methylaniline,
N,N-bis(.beta.-hydroxyethyl)-para-phenylenediamine,
4-amino-N,N-bis(.beta.-hydroxyethyl)-2-methylaniline,
4-amino-2-chloro-N,N-bis(.beta.-hydroxyethyl)aniline,
2-.beta.-hydroxyethyl-para-phenylenediamine,
2-fluoro-para-phenylenediami- ne,
2-isopropyl-para-phenylenediamine,
N-(.beta.-hydroxypropyl)-para-pheny- lenediamine,
2-hydroxymethyl-para-phenylenediamine,
N,N-dimethyl-3-methyl-para-phenylenediamine,
N,N-(ethyl-.beta.-hydroxyeth- yl)-para-phenylenediamine,
N-(.beta.,.gamma.-dihydroxypropyl)-para-phenyle- nediamine,
N-(4'-aminophenyl)-para-phenylenediamine,
N-phenyl-para-phenylenediamine,
2-.beta.-hydroxyethyloxy-para-phenylenedi- amine,
2-.beta.-acetylaminoethyloxy-para-phenylenediamine,
N-(.beta.-methoxyethyl)-para-phenylenediamine, and acid addition
salts thereof.
13. A composition according to claim 9, wherein said double bases
are chosen from compounds of formula (III) below and acid addition
salts thereof: 72wherein: Z.sub.1 and Z.sub.2, which may be
identical or different, are chosen from a hydroxyl radical and an
--NH.sub.2 radical which may be substituted with a C.sub.1-C.sub.4
alkyl radical or with a linker arm G; the linker arm G is chosen
from linear alkylene chains comprising from 1 to 14 carbon atoms
and branched alkylene chains comprising from 2 to 14 carbon atoms,
wherein said chains may be interrupted by or terminated with at
least one nitrogenous group and/or at least one hetero atom and
optionally substituted with at least one radical chosen from
hydroxyl and C.sub.1-C.sub.6 alkoxy radicals; R.sub.22 and R.sub.23
are chosen from hydrogen and halogen atoms, C.sub.1-C.sub.4 alkyl
radicals, C.sub.1-C.sub.4 monohydroxyalkyl radicals,
C.sub.2-C.sub.4 polyhydroxyalkyl radicals, C.sub.1-C.sub.4
aminoalkyl radicals, and a linker arm G; R.sub.24, R.sub.25,
R.sub.26, R.sub.27, R.sub.28 and R.sub.29, which may be identical
or different, are chosen from a hydrogen atom, a linker arm G and
C.sub.1-C.sub.4 alkyl radicals; with the proviso that the compounds
of formula (III) contain only one linker arm G per molecule.
14. A composition according to claim 13, wherein said at least one
hetero atom in said linker arm G is chosen from oxygen, sulphur,
and nitrogen atoms.
15. A composition according to claim 13, wherein said double bases
of formula (III) are chosen from
N,N'-bis(.beta.-hydroxyethyl)-N,N'-bis(4'-a-
minophenyl)-1,3-diaminopropanol,
N,N'-bis(.beta.-hydroxyethyl)-N,N'-bis(4'-
-aminophenyl)ethylenediamine,
N,N'-bis(4-aminophenyl)tetramethylenediamine- ,
N,N'-bis(.beta.-hydroxyethyl)-N,N'-bis(4-aminophenyl)tetramethylenediami-
ne, N,N'-bis(4-methylaminophenyl)tetramethylenediamine,
N,N'-bis(ethyl)-N,N'-bis(4'-amino-3'-methylphenyl)ethylenediamine,
1,8-bis(2,5-diaminophenoxy)-3,5-dioxaoctane, and acid addition
salts thereof.
16. A composition according to claim 9, wherein said
para-aminophenols are chosen from compounds of formula (IV) below
and acid addition salts thereof: 73wherein: R.sub.30 is chosen from
hydrogen and halogen atoms, C.sub.1-C.sub.4 alkyl radicals,
C.sub.1-C.sub.4 monohydroxyalkyl radicals,
(C.sub.1-C.sub.4)alkoxy(C.sub.1-C.sub.4)alkyl radicals,
C.sub.1-C.sub.4 aminoalkyl radicals, and
hydroxy(C.sub.1-C.sub.4)alkylami- no(C.sub.1-C.sub.4)alkyl
radicals, R.sub.31 is chosen from hydrogen and halogen atoms,
C.sub.1-C.sub.4-alkyl radicals, C.sub.1-C.sub.4 monohydroxyalkyl
radicals, C.sub.2-C.sub.4 polyhydroxyalkyl radicals,
C.sub.1-C.sub.4 aminoalkyl radicals, C.sub.1-C.sub.4 cyanoalkyl
radicals, and (C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl
radicals, with the proviso that at least one of the radicals
R.sub.30 and R.sub.31 is a hydrogen atom.
17. A composition according to claim 16, wherein said
para-aminophenols of formula (IV) are chosen from para-aminophenol,
4-amino-3-methylphenol, 4-amino-3-fluorophenol,
4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol,
4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol,
4-amino-2-aminomethylphenol,
4-amino-2-(.beta.-hydroxyethylaminomethyl)phenol,
4-amino-2-fluorophenol, and acid addition salts thereof.
18. A composition according to claim 9, wherein said
ortho-aminophenols are chosen from 2-aminophenol,
2-amino-5-methylphenol, 2-amino-6-methylphenol,
5-acetamido-2-aminophenol, and acid addition salts thereof.
19. A composition according to claim 9, wherein said heterocyclic
oxidation bases are chosen from pyridines, pyrimidines, pyrazoles,
and acid addition salts thereof.
20. A composition according to claim 1, wherein said at least one
oxidation base is present in an amount ranging from about 0.0005 to
about 12% by weight relative to the total weight of the dye
composition.
21. A composition according to claim 20, wherein said at least one
oxidation base is present in an amount ranging from about 0.005 to
about 6% by weight relative to the total weight of the dye
composition.
22. A composition according to claim 1, wherein said at least one
cationic direct dye of formula (I) is chosen from:
4'-dimethylaminophenyl-2-azopyr- idine N-oxide of formula:
744'-dimethylamino-2'-methylphenyl-2-azopyridin- e N-oxide of
formula: 752-[(1,3-diamino-6-methyl-4-phenyl)azo]-3-methyl
benzothiazolium iodide of formula:
766'-hydroxybenzomorpholine-7'-aza-2-- methyl-3-benzothiazolium
chloride of formula: 776'-hydroxybenzomorpholine-
-7'-aza-2-methyl-4-phenyl-3-thiazolium perchlorate of formula:
786'-hydroxybenzomorpholine-7'-azo-2-diphenyl-3,4-thiazolium
perchlorate of formula:
796'-hydroxybenzomorpholine-7'-aza-2-methyl-3-benzothiazoliu- m
chloride of formula:
806'-hydroxybenzomorpholine-7'-aza-2-methyl-4-phen- yl-3-thiazolium
perchlorate of formula: 812',4'-diamino-5'-methoxyphenyl--
2-azopyridine N-oxide of formula:
822'-acetamido-4'-hydroxy-5'-methylphen- yl-2-azopyridine N-oxide
of formula: 832'-acetamido-4'-dimethylaminopheny- l-2-azopyridine
N-oxide of formula: 842'-amino-4'-dimethylaminophenyl-2-a-
zopyridine N-oxide of formula: 852',4'-diamino-5'-methyl
phenyl-2-azomethoxy-1-pyridinium perchlorate of formula:
862',5'-dimethyl-4'-hydroxyphenyl-2-azopyridine N-oxide of formula:
872'-dimethylamino-4'-hydroxyphenyl-2-azopyridine N-oxide of
formula: 884'-dimethylamino-2'-hydroxyphenyl-2-azopyridine N-oxide
of formula: 893',5'-dimethyl-4'-hydroxyphenyl-2-azopyridine N-oxide
of formula: 904'-dimethylamino-2'-nitrophenyl-2-azopyridine N-oxide
of formula: 918'-hydroxyquinoline-5':2'-azopyridine N-oxide of
formula:
922'-nitro-4'-dimethylaminophenyl-2-azomethoxy-1-pyridinium
methosulphate of formula:
934'-dimethylaminophenyl-2-azo-5-nitropyridine N-oxide of formula:
944'-dimethylaminophenyl-2-azo-6-nitropyridine N-oxide of formula:
954'-dimethylaminophenyl-2-azo-5-methylpyridine N-oxide of formula:
964'-dimethylaminophenyl-2-azo-3-methyl pyridine N-oxide of
formula: 974'-diethylaminophenyl-2-azo-3-methylpyridine N-oxide of
formula:
984'-dimethylamino-2'-acetylaminophenyl-2-azo-3-methylpyridine
N-oxide of formula: 994'-aminonaphthalene-1':2-azo-6-methylpyridine
N-oxide of formula:
1004'-di(.beta.-hydroxyethyl)aminophenyl-2-azo-6-met- hylpyridine
N-oxide of formula: 1014'-diethylaminophenyl-2-azo-6-methylpy-
ridine N-oxide of formula:
1022',5'-dimethyl-4'-hydroxyphenyl-2-azo-6-met- hylpyridine N-oxide
of formula: 1034'-di(.beta.-hydroxyethyl)aminophenyl--
2-azo-4-methylpyridine N-oxide of formula:
1044'-diethylaminophenyl-2-azo- -4-methyl pyridine N-oxide of
formula: 1054'-aminonaphthalene-1':2-azo-4-- methylpyridine N-oxide
of formula: 1062',4'-diamino-5'-methylphenyl-2-azo-
-2-4-methylpyridine N-oxide of formula: 1074'-dimethylamino
phenyl-2-azo-4-methylpyridine N-oxide of formula:
1084'-dimethylaminophenyl-2-azo-4,6-dimethylpyridine N-oxide of
formula: 1092',5'-dimethyl-4'-hydroxyphenyl-2-azo-4-methylpyridine
N-oxide of formula:
1104'-dimethylaminophenyl-2-azo-5-chloropyridine N-oxide of
formula: 1114'-dimethylamino-2'-methylphenyl-2-azo-5-chloropyridine
N-oxide of formula: 1124'-diethylaminophenyl-2-azo-5-chloropyridine
N-oxide of formula: 1136'-hydroxybenzomorpholine-7':2-azopyridine
N-oxide of formula:
1146'-hydroxybenzomorpholine-7':2-azo-1-methoxypyrid- inium
methosulphate of formula:
1152',4'-diamino-5'-methylphenyl-2-azopyr- idine N-oxide of
formula: 1162'-methyl-5'-oxo-4'-phenyldihydropyrazolyl-2-
-azo-1-methoxypyridinium methosulphate of formula:
1173'-methyl-2',4',6'-trioxohexahydropyrimidinyl-2-azopyridine
N-oxide of formula: 1184'-aminophenyl-2-azopyridine N-oxide of
formula: 1194'-di(.beta.-hydroxyethyl)aminophenyl-2-azopyridine
N-oxide of formula: 1204'-(N-phenylamino)phenyl-2-azopyridine
N-oxide of formula:
1214'-(N-phenylamino)phenyl-2-azo-3-methylpyridine N-oxide of
formula: 1224'-aminophenyl-2-azo-1,3-dimethylpyridinium
methosulphate of formula:
1234'-di(.beta.-hydroxyethyl)aminophenyl-2-azo-1,4-dimethylpyridinium
methosulphate of formula:
1244'-dimethylaminophenyl-2-azo-1,3-dimethylpy- ridinium
methosulphate of formula: 1254'-N-phenylaminophenyl-2-azo-1,6-di-
methylpyridinium methosulphate of formula:
1264'-dimethylaminophenyl-2-az- o-1,5-dimethylpyridinium
methosulphate of formula:
1274'-dimethylaminophenyl-2-azo-1,6-dimethylpyridinium
methosulphate of formula:
1282',4',6'-trioxohexahydropyrimidinyl-2-azopyridine N-oxide of
formula:
1294'-dimethylaminophenyl-2-azo-1,3-dimethylbenzimidazolium
perchlorate of formula: 1302',4'-diamino-3'-pyridine-2-azopyridine
N-oxide of formula: 131
23. A composition according to claim 1, wherein said at least one
cationic direct dye of formula (I) is present in an amount ranging
from about 0.001 to about 10% by weight relative to the total
weight of the dye composition.
24. A composition according to claim 23, wherein said at least one
cationic direct dye of formula (I) is present in an amount ranging
from about 0.01 to about 5% by weight relative to the total weight
of the dye composition.
25. A composition according to claim 1, further comprising at least
one ingredient chosen from couplers and direct dyes other than said
at least one cationic direct dye of formula (I).
26. A composition according to claim 25, wherein said couplers are
chosen from meta-phenylenediamines, meta-aminophenols,
meta-diphenols, heterocyclic couplers, and acid addition salts
thereof.
27. A composition according to claim 25, wherein said at least one
ingredient is chosen from couplers and is present in an amount
ranging from about 0.0001 to about 10% by weight relative to the
total weight of the dye composition.
28. A composition according to claim 27, wherein said at least one
ingredient is chosen from couplers and is present in an amount
ranging from about 0.005 to about 5% by weight relative to the
total weight of the dye composition.
29. A composition according to claim 10, wherein said acid addition
salts are chosen from hydrochloride, hydrobromide, sulphate,
tartrate, lactate, and acetate.
30. A composition according to claim 12, wherein said acid addition
salts are chosen from hydrochloride, hydrobromide, sulphate,
tartrate, lactate, and acetate.
31. A composition according to claim 13, wherein said acid addition
salts are chosen from hydrochloride, hydrobromide, sulphate,
tartrate, lactate, and acetate.
32. A composition according to claim 15, wherein said acid addition
salts are chosen from hydrochloride, hydrobromide, sulphate,
tartrate, lactate, and acetate.
33. A composition according to claim 16, wherein said acid addition
salts are chosen from hydrochloride, hydrobromide, sulphate,
tartrate, lactate, and acetate.
34. A composition according to claim 17, wherein said acid addition
salts are chosen from hydrochloride, hydrobromide, sulphate,
tartrate, lactate, and acetate.
35. A composition according to claim 18, wherein said acid addition
salts are chosen from hydrochloride, hydrobromide, sulphate,
tartrate, lactate, and acetate.
36. A composition according to claim 19, wherein said acid addition
salts are chosen from hydrochloride, hydrobromide, sulphate,
tartrate, lactate, and acetate.
37. A composition according to claim 26, wherein said acid addition
salts are chosen from hydrochloride, hydrobromide, sulphate,
tartrate, lactate, and acetate.
38. A method for dyeing keratin fibres, comprising: applying to
said keratin fibres for a time sufficient to achieve colour
development, a composition comprising: at least one oxidation base,
at least one cationic direct dye of formula (I) below:
A--N.dbd.N--B (I) wherein: A is chosen from structures A1, A2, and
A3 below: 132wherein in said structures A1 to A3: R.sub.1 is chosen
from C.sub.1-C.sub.4 alkyl radicals, a phenyl radical, and phenyl
radicals having a substituent chosen from C.sub.1-C.sub.4 alkyl
radicals and halogen atoms chosen from chlorine, bromine, iodine
and fluorine; R.sub.2 is chosen from C.sub.1-C.sub.4 alkyl radicals
and a phenyl radical; R.sub.3 and R.sub.4, which may be identical
or different, are chosen from C.sub.1-C.sub.4 alkyl radicals and a
phenyl radical or together form a benzene ring having at least one
substituent chosen from C.sub.1-C.sub.4 alkyl radicals,
C.sub.1-C.sub.4 alkoxy radicals, and nitro radicals; R.sub.3 can
also be a hydrogen atom; R.sub.5 and R.sub.6, which may be
identical or different, are chosen from C.sub.1-C.sub.4 alkyl
radicals and a phenyl radical or together form a benzene ring which
is unsubstituted or has at least one substituent chosen from
C.sub.1-C.sub.4 alkyl radicals, C.sub.1-C.sub.4 alkoxy radicals,
and nitro radicals; R.sub.5 can also be a hydrogen atom; R.sub.7
and R.sub.8, which may be identical or different, are chosen from a
hydrogen atom, halogen atoms chosen from chlorine, bromine, iodine
and fluorine, C.sub.1-C.sub.4 alkyl radicals, C.sub.1-C.sub.4
alkoxy radicals and nitro radicals; Z is chosen from an oxygen
atom, a sulphur atom, and a group NR.sub.2, wherein R.sub.2 is
chosen from C.sub.1-C.sub.4 alkyl radicals and a phenyl radical;
the ring member L is chosen from --CH, --CR and
--N.sup.+R.sub.9(X.sup.-).sub.r; the ring member M is chosen from
--CH, --CR and --N.sup.+R.sub.9(X.sup.-)- .sub.r; r is an integer
equal to 0 or 1; R is chosen from C.sub.1-C.sub.4 alkyl radicals;
R.sub.9 is chosen from an atom O.sup.-, C.sub.1-C.sub.4 alkyl
radicals, and C.sub.1-C.sub.4 alkoxy radicals; X.sup.- is chosen
from an anion; with the provisos that: in said formula A3, at least
one of the ring members L and M is a group
--N.sup.+R.sub.9(X.sup.-).sub.r; when R.sub.6 is a C.sub.1-C.sub.4
alkyl radical and Z is a sulphur atom, then R.sub.5 is other than a
C.sub.1-C.sub.4 alkyl radical; when R.sub.6 is a C.sub.1-C.sub.4
alkyl radical and Z is a sulphur atom and when one of the radicals
R.sub.10 and R.sub.11 is a hydrogen atom, then R.sub.5 is other
than a hydrogen atom; when R.sub.9 is O.sup.-, then r=0; when L or
M is a radical --N.sup.+R.sub.9(X.sup.-).sub.r wherein R.sub.9 is a
C.sub.1-C.sub.4 alkyl radical and r=1, then at least one of the
radicals R.sub.7 and R.sub.8 is other than a hydrogen atom; when L
is a radical --N.sup.+R.sub.9(X.sup.-).sub.r, then M is chosen from
--CH and CR; when M is a radical --N.sup.+R.sub.9(X.sup.-).sub.r,
then L is chosen from --CH and CR; when Z is a group NR.sub.2
wherein R.sub.2 is a C.sub.1-C.sub.4 alkyl radical, then at least
one of the radicals R.sub.1, R.sub.5 and R.sub.6 is other than a
C.sub.1-C.sub.4 alkyl radical; when Z is a sulphur atom and R.sub.1
is a C.sub.1-C.sub.4 alkyl radical and when one of the radicals
R.sub.10 and R.sub.11 is a hydrogen atom, then R.sub.5 and R.sub.6
cannot together form an unsubstituted benzene ring; B is chosen
from: (a) a group of structure B1 below: 133wherein in structure
B1, R.sub.10 is chosen from a hydrogen atom, halogen atoms chosen
from chlorine, bromine, iodine and fluorine, C.sub.1-C.sub.4 alkyl
radicals, C.sub.1-C.sub.4 alkoxy radicals, a hydroxyl radical,
--NHR.sub.13 groups, --NR.sub.14R.sub.15groups,
--NHCO(C.sub.1-C.sub.4)al- kyl groups and a nitro, or forms with
R.sub.11 a 5- or 6-membered carbon ring or a ring containing at
least one hetero atom chosen from nitrogen, oxygen and sulphur;
R.sub.11 is chosen from a hydrogen atom, halogen atoms chosen from
chlorine, bromine, iodine and fluorine, C.sub.1-C.sub.4 alkyl
radicals, and C.sub.1-C.sub.4 alkoxy radicals or forms with
R.sub.12 or R.sub.13 a 5- or 6-membered carbon ring or a ring
containing at least one hetero atom chosen from nitrogen, oxygen
and sulphur; R.sub.12 is chosen from a hydrogen atom, a hydroxyl
radical, --NHR.sub.13 radicals, and --NR.sub.14R.sub.15 radicals;
R.sub.13 is chosen from a hydrogen atom, C.sub.1-C.sub.4 alkyl
radicals, C.sub.1-C.sub.4 monohydroxyalkyl radicals,
C.sub.2-C.sub.4 polyhydroxyalkyl radicals, and a phenyl radical;
R.sub.14 and R.sub.15, which may be identical or different, are
chosen from C.sub.1-C.sub.4 alkyl radicals, C.sub.1-C.sub.4
monohydroxyalkyl radicals, and C.sub.2-C.sub.4 polyhydroxyalkyl
radicals; and (b) a 5- or 6-membered nitrogenous heterocyclic
group, a 5- or 6-membered nitrogenous heterocyclic group comprising
at least one additional hetero atom chosen from oxygen and sulphur
and/or at least one carbonyl group, wherein said heterocycles are
unsubstituted or have at least one substituent chosen from
C.sub.1-C.sub.4 alkyl, amino and phenyl radicals.
39. The method according to claim 38, wherein said composition
further comprises an oxidizing agent.
40. The method according to claim 38, wherein said colour is
developed at an acidic, neutral, or alkaline pH by an oxidizing
agent added sequentially at the time of applying said composition
to said fibres, or added simultaneously at the time of applying
said composition to said fibres.
41. The method according to claim 38, wherein said keratin fibres
are human keratin fibres.
42. The method according to claim 41, wherein said human keratin
fibres are human hair.
43. The method according to claim 38, wherein said time sufficient
ranges from about 3 to about 50 minues.
44. The method according to claim 43, wherein said time sufficient
ranges from about 5 to about 30 minutes.
45. The method according to claim 39, wherein said oxidizing agent
present in the oxidizing composition is chosen from hydrogen
peroxide, urea peroxide, alkali metal bromates, persalts, peracids
and enzymes.
46. The method according to claim 45, wherein said persalts are
perborates, percarbonates, and persulfates.
47. The method according to claim 39, wherein said oxidizing agent
is hydrogen peroxide.
48. A multi-compartment dyeing device or kit for dyeing keratin
fibres, comprising at least two separate compartments: a first
compartment comprising an oxidizing composition, and a second
compartment comprising the following composition: at least one
oxidation base, at least one cationic direct dye of formula (I)
below: A--N.dbd.N--B (I) wherein: A is chosen from structures A1,
A2, and A3 below: 134wherein in said structures A1 to A3: R.sub.1
is chosen from C.sub.1-C.sub.4 alkyl radicals, a phenyl radical,
and phenyl radicals having a substituent chosen from
C.sub.1-C.sub.4 alkyl radicals and halogen atoms chosen from
chlorine, bromine, iodine and fluorine; R.sub.2 is chosen from
C.sub.1-C.sub.4 alkyl radicals and a phenyl radical; R.sub.3 and
R.sub.4, which may be identical or different, are chosen from
C.sub.1-C.sub.4 alkyl radicals and a phenyl radical or together
form a benzene ring having at least one substituent chosen from
C.sub.1-C.sub.4 alkyl radicals, C.sub.1-C.sub.4 alkoxy radicals,
and nitro radicals; R.sub.3 can also be a hydrogen atom; R.sub.5
and R.sub.6, which may be identical or different, are chosen from
C.sub.1-C.sub.4 alkyl radicals and a phenyl radical or together
form a benzene ring which is unsubstituted or has at least one
substituent chosen from C.sub.1-C.sub.4 alkyl radicals,
C.sub.1-C.sub.4 alkoxy radicals, and nitro radicals; R.sub.5 can
also be a hydrogen atom; R.sub.7 and R.sub.8, which may be
identical or different, are chosen from a hydrogen atom, halogen
atoms chosen from chlorine, bromine, iodine and fluorine,
C.sub.1-C.sub.4 alkyl radicals, C.sub.1-C.sub.4 alkoxy radicals and
nitro radicals; Z is chosen from an oxygen atom, a sulphur atom,
and a group NR.sub.2, wherein R.sub.2 is chosen from
C.sub.1-C.sub.4 alkyl radicals and a phenyl radical; the ring
member L is chosen from --CH, --CR and
--N.sup.+R.sub.9(X.sup.-).sub.r; the ring member M is chosen from
--CH, --CR and --N.sup.+R.sub.9(X.sup.-)- .sub.r; r is an integer
equal to 0 or 1; R is chosen from C.sub.1-C.sub.4 alkyl radicals;
R.sub.9 is chosen from an atom O.sup.-, C.sub.1-C.sub.4 alkyl
radicals, and C.sub.1-C.sub.4 alkoxy radicals; X.sup.- is chosen
from an anion; with the provisos that: in said formula A3, at least
one of the ring members L and M is a group
--N.sup.+R.sub.9(X.sup.-).sub.r; when R.sub.6 is a C.sub.1-C.sub.4
alkyl radical and Z is a sulphur atom, then R.sub.5 is other than a
C.sub.1-C.sub.4 alkyl radical; when R.sub.6 is a C.sub.1-C.sub.4
alkyl radical and Z is a sulphur atom and when one of the radicals
R.sub.10 and R.sub.11 is a hydrogen atom, then R.sub.5 is other
than a hydrogen atom; when R.sub.9 is O.sup.-, then r=0; when L or
M is a radical --N.sup.+R.sub.9(X.sup.-).sub.r wherein R.sub.9 is a
C.sub.1-C.sub.4 alkyl radical and r=1, then at least one of the
radicals R.sub.7 and R.sub.8 is other than a hydrogen atom; when L
is a radical --N.sup.+R.sub.9(X.sup.-).sub.r, then M is chosen from
--CH and CR; when M is a radical --N.sup.+R.sub.9(X.sup.-).sub.r,
then L is chosen from --CH and CR; when Z is a group NR.sub.2
wherein R.sub.2 is a C.sub.1-C.sub.4 alkyl radical, then at least
one of the radicals R.sub.1, R.sub.5 and R.sub.6 is other than a
C.sub.1-C.sub.4 alkyl radical; when Z is a sulphur atom and R.sub.1
is a C.sub.1-C.sub.4 alkyl radical and when one of the radicals
R.sub.10 and R.sub.11 is a hydrogen atom, then R.sub.5 and R.sub.6
cannot together form an unsubstituted benzene ring; B is chosen
from: (a) a group of structure B1 below: 135wherein in structure
B1, R.sub.10 is chosen from a hydrogen atom, halogen atoms chosen
from chlorine, bromine, iodine and fluorine, C.sub.1-C.sub.4 alkyl
radicals, C.sub.1-C.sub.4 alkoxy radicals, a hydroxyl radical,
--NHR.sub.13 groups, --NR.sub.14R.sub.15 groups,
--NHCO(C.sub.1-C.sub.4)a- lkyl groups and a nitro, or forms with
R.sub.1 a 5- or 6-membered carbon ring or a ring containing at
least one hetero atom chosen from nitrogen, oxygen and sulphur;
R.sub.11 is chosen from a hydrogen atom, halogen atoms chosen from
chlorine, bromine, iodine and fluorine, C.sub.1-C.sub.4 alkyl
radicals, and C.sub.1-C.sub.4 alkoxy radicals or forms with
R.sub.12 or R.sub.13 a 5- or 6-membered carbon ring or a ring
containing at least one hetero atom chosen from nitrogen, oxygen
and sulphur; R.sub.12 is chosen from a hydrogen atom, a hydroxyl
radical, --NHR.sub.13 radicals, and --NR.sub.14R.sub.15 radicals;
R.sub.13 is chosen from a hydrogen atom, C.sub.1-C.sub.4 alkyl
radicals, C.sub.1-C.sub.4 monohydroxyalkyl radicals,
C.sub.2-C.sub.4 polyhydroxyalkyl radicals, and a phenyl radical;
R.sub.14 and R.sub.15, which may be identical or different, are
chosen from C.sub.1-C.sub.4 alkyl radicals, C.sub.1-C.sub.4
monohydroxyalkyl radicals, and C.sub.2-C.sub.4 polyhydroxyalkyl
radicals;; and (b) a 5- or 6-membered nitrogenous heterocyclic
group, a 5- or 6-membered nitrogenous heterocyclic group comprising
at least one additional hetero atom chosen from oxygen and sulphur
and/or at least one carbonyl group, wherein said heterocycles are
unsubstituted or have at least one substituent chosen from
C.sub.1-C.sub.4 alkyl, amino and phenyl radicals.
49. A composition according to claim 1, in the form of a liquid,
cream, gel, or any other form suitable for dyeing keratin fibres.
Description
[0001] The invention relates to a composition for the oxidation
dyeing of keratin fibres, especially human keratin fibres such as
the hair, comprising, in a medium suitable for dyeing, at least one
oxidation base and at least one specific cationic dye as direct
dye, as well as to the dyeing process using this composition.
[0002] It is known to dye keratin fibres, particularly human hair,
with dye compositions containing oxidation dye precursors, in
particular ortho- or para-phenylenediamines, ortho- or
para-aminophenols and heterocyclic bases, generally referred to as
oxidation bases. Oxidation dye precursors, or oxidation bases, are
colourless or weakly coloured compounds which, when combined with
oxidizing products, can give rise to coloured compounds and dyes by
a process of oxidative condensation.
[0003] It is also known that the shades obtained with these
oxidation bases can be varied by combining them with couplers or
colour modifiers, the latter being chosen in particular from
aromatic meta-diamines, meta-aminophenols, meta-diphenols and
certain heterocyclic compounds.
[0004] The variety of compounds used as oxidation bases and
couplers allows a wide range of colours to be obtained.
[0005] It is also known that direct dyes, i.e., coloured substances
which give a coloration in the absence of an oxidizing agent, can
be used, in combination with the oxidation dye precursors and the
couplers, to further vary the shades obtained and to give them
glints.
[0006] The vast majority of these direct dyes belong to the family
of nitrobenzene compounds and have the drawback, when they are
incorporated into dye compositions, of leading to colorations which
show insufficient staying power, especially with respect to
shampooing.
[0007] The so-called "permanent" coloration obtained by these
oxidation dyes should, moreover, satisfy a certain number of
objectives. The dyes should allow shades to be obtained in the
desired intensity and should show good resistance to external
agents (light, bad weather, washing, permanent-waving,
perspiration, rubbing).
[0008] The dyes should also be able to cover grey hair and,
finally, they should be as unselective as possible, i.e., they
should allow only the smallest possible colour differences along
the same keratin fibre, which may indeed be differently sensitized,
i.e., damaged, between its tip and its root.
[0009] The present invention is directed towards proposing novel
compositions for the oxidation dyeing of keratin fibres, especially
human keratin fibres such as the hair, which produce colorations
that are preferably rich in glints while at the same time having
good properties of staying power.
[0010] Thus, the inventors have discovered that it is possible to
obtain novel dyes which are can be both rich in glints and have
good staying power by combining:
[0011] at least one oxidation base,
[0012] at least one cationic direct dye of formula (I) defined
below.
[0013] This discovery forms the basis of the present invention.
[0014] Additional features and advantages of the invention are set
forth in the description that follows, and, in part, will be
apparent from the description or may be learned from practice of
the invention. The advantages of the invention will be realized and
attained by the dyeing compositions, processes, and kits
particularly pointed out in the written description and claims.
[0015] Both the foregoing general description and the following
detailed description of the invention are exemplary and explanatory
only and are not restrictive of the claimed invention.
[0016] A first subject of the invention is a composition for the
oxidation dyeing of keratin fibres, especially human keratin fibres
such as the hair, comprising, in a medium suitable for dyeing:
[0017] at least one oxidation base,
[0018] at least one cationic direct dye of formula (I) below:
A--N.dbd.N--B (I)
[0019] wherein:
[0020] A is chosen from structures A1, A2, and A3 below: 1
[0021] wherein in said structures A1 to A3:
[0022] R.sub.1 is chosen from C.sub.1-C.sub.4 alkyl radicals, a
phenyl radical, and phenyl radicals having a substituent chosen
from C.sub.1-C.sub.4 alkyl radicals and halogen atoms chosen from
chlorine, bromine, iodine and fluorine;
[0023] R.sub.2 is chosen from C.sub.1-C.sub.4 alkyl radicals and a
phenyl radical;
[0024] R.sub.3 and R.sub.4, which may be identical or different,
are chosen from C.sub.1-C.sub.4 alkyl radicals and a phenyl radical
or together form a benzene ring having at least one substituent
chosen from C.sub.1-C.sub.4 alkyl radicals, C.sub.1-C.sub.4 alkoxy
radicals, and nitro radicals; R.sub.3 can also be a hydrogen
atom;
[0025] R.sub.5 and R.sub.6, which may be identical or different,
are chosen from C.sub.1-C.sub.4 alkyl radicals and a phenyl radical
or together form a benzene ring which is unsubstituted or has at
least one substituent chosen from C.sub.1-C.sub.4 alkyl radicals,
C.sub.1-C.sub.4 alkoxy radicals, and nitro radicals; R.sub.5 can
also be a hydrogen atom;
[0026] R.sub.7 and R.sub.8, which may be identical or different,
are chosen from a hydrogen atom, halogen atoms chosen from
chlorine, bromine, iodine and fluorine, C.sub.1-C.sub.4 alkyl
radicals, C.sub.1-C.sub.4 alkoxy radicals and nitro radicals;
[0027] Z is chosen from an oxygen atom, a sulphur atom, and a group
NR.sub.2, wherein R.sub.2 is chosen from C.sub.1-C.sub.4 alkyl
radicals and a phenyl radical;
[0028] the ring member L is chosen from --CH, --CR and
--N.sup.+R.sub.9(X.sup.-).sub.r;
[0029] the ring member M is chosen from --CH, --CR and
--N.sup.+R.sub.9(X.sup.-).sub.r;
[0030] r is an integer equal to 0 or 1;
[0031] R is chosen from C.sub.1-C.sub.4 alkyl radicals;
[0032] R.sub.9 is chosen from an atom O.sup.-, C.sub.1-C.sub.4
alkyl radicals, and C.sub.1-C.sub.4 alkoxy radicals;
[0033] X.sup.- is chosen from an anion preferably chloride, methyl
sulphate, ethyl sulphate, acetate, and perchlorate;
[0034] with the provisos that:
[0035] in the formula A3, at least one of the ring members L and M
is chosen from a group --N.sup.+R.sub.9(X.sup.-).sub.r;
[0036] when R.sub.6 is a C.sub.1-C.sub.4 alkyl radical and Z is a
sulphur atom, then R.sub.5 is other than a C.sub.1-C.sub.4 alkyl
radical;
[0037] when R.sub.6 is a C.sub.1-C.sub.4 alkyl radical and Z is a
sulphur atom and when one of the radicals R.sub.10 and R.sub.11,
defined below, is a hydrogen atom, then R.sub.5 is other than a
hydrogen atom;
[0038] when R.sub.9 is O.sup.-, then r=0;
[0039] when L or M is a radical --N.sup.+R.sub.9(X.sup.-).sub.r
wherein R.sub.9 is a C.sub.1-C.sub.4 alkyl radical and r=1, then at
least one of the radicals R.sub.7 and R.sub.8 is other than a
hydrogen atom;
[0040] when L is a radical --N.sup.+R.sub.9(X.sup.-).sub.r, then M
is chosen from a group --CH and CR;
[0041] when M is a radical --N.sup.+R.sub.9(X.sup.-).sub.r, then L
is chosen from a group --CH and CR;
[0042] when Z is a group NR.sub.2 wherein R.sub.2 is a
C.sub.1-C.sub.4 alkyl radical, then at least one of the radicals
R.sub.1, R.sub.5 and R.sub.6 is other than a C.sub.1-C.sub.4 alkyl
radical;
[0043] when Z is a sulphur atom and R.sub.1 is a C.sub.1-C.sub.4
alkyl radical and when one of the radicals R.sub.10 and R.sub.11,
defined below, is a hydrogen atom, then R.sub.5 and R.sub.6 cannot
together form an unsubstituted benzene ring;
[0044] B is chosen from:
[0045] (a) a group of structure B1 below: 2
[0046] wherein in structure B1,
[0047] R.sub.10 is chosen from a hydrogen atom, halogen atoms
chosen from chlorine, bromine, iodine and fluorine, C.sub.1-C.sub.4
alkyl radicals, C.sub.1-C.sub.4 alkoxy radicals, a hydroxyl
radical, --NHR.sub.13 groups, --NR.sub.14R.sub.15groups,
--NHCO(C.sub.1-C.sub.4)alkyl groups and a nitro, or forms with
R.sub.11 a 5- or 6-membered carbon ring or a ring containing at
least one hetero atom chosen from nitrogen, oxygen and sulphur;
[0048] R.sub.11 is chosen from a hydrogen atom, halogen atoms
chosen from chlorine, bromine, iodine and fluorine, C.sub.1-C.sub.4
alkyl radicals, and C.sub.1-C.sub.4 alkoxy radicals or forms with
R.sub.12 or R.sub.13 a 5- or 6-membered carbon ring or a ring
containing at least one hetero atom chosen from nitrogen, oxygen
and sulphur;
[0049] R.sub.12 is chosen from a hydrogen atom, a hydroxyl radical,
--NHR.sub.13 radicals, and --NR.sub.14R.sub.15 radicals;
[0050] R.sub.13 is chosen from a hydrogen atom, C.sub.1-C.sub.4
alkyl radicals, C.sub.1-C.sub.4 monohydroxyalkyl radicals,
C.sub.2-C.sub.4 polyhydroxyalkyl radicals, and a phenyl
radical;
[0051] R.sub.14 and R.sub.15, which may be identical or different,
are chosen from C.sub.1-C.sub.4 alkyl radicals, C.sub.1-C.sub.4
monohydroxyalkyl radicals, and C.sub.2-C.sub.4 polyhydroxyalkyl
radicals; and
[0052] (b) a 5- or 6-membered nitrogenous heterocyclic group, a 5-
or 6-membered nitrogenous heterocyclic group comprising at least
one additional hetero atom chosen from oxygen and sulphur and/or at
least one carbonyl group, wherein said heterocycles are
unsubstituted or have at least one substituent chosen from
C.sub.1-C.sub.4 alkyl, amino and phenyl radicals.
[0053] Among the said 5- or 6-membered nitrogenous heterocyclic
groups featured above, preferred compounds include groups of
structure B2 below: 3
[0054] wherein in structure B2:
[0055] R.sub.16 and R.sub.17, which may be identical or different,
are chosen from a hydrogen atom, C.sub.1-C.sub.4 alkyl radicals and
a phenyl radical;
[0056] Y is chosen from 4
[0057] n is an integer equal to 0 or 1.
[0058] The cationic direct dyes of formula (I) above are known
compounds of the prior art and are described, for example, in
patent application FR-A-2,140,205 and its Certificates of Addition,
as well as in patent application FR-A-2,189,006, the disclosures of
which are specifically incorporated by reference herein.
[0059] The dye composition according to the invention can give
intense, chromatic colorations which show little selectivity and
excellent properties of resistance both with respect to atmospheric
agents such as light and bad weather, and with respect to
perspiration and the various treatments to which hair may be
subjected. These properties can be particularly noteworthy with
respect to chromaticity.
[0060] Another subject of the invention is a process for the
oxidation dyeing of keratin fibres using this dye composition.
[0061] In the compounds of formula (I) above, the C.sub.1-C.sub.4
alkyl and alkoxy radicals are preferably chosen from the methyl,
ethyl, butyl, methoxy and ethoxy radicals.
[0062] The nature of the oxidation base(s) used in the dye
composition according to the invention is not a critical factor.
They can be chosen, for example, from para-phenylenediamines,
double bases, para-aminophenols, ortho-aminophenols and
heterocyclic oxidation bases.
[0063] Among the para-phenylenediamines which can be used as
oxidation bases in the dye compositions according to the invention,
examples include the compounds of formula (II) below, and the
addition salts thereof with an acid: 5
[0064] wherein:
[0065] R.sub.18 is chosen from a hydrogen atom, C.sub.1-C.sub.4
alkyl radicals, C.sub.1-C.sub.4 monohydroxyalkyl radicals,
C.sub.2-C.sub.4 polyhydroxyalkyl radicals,
(C.sub.1-C.sub.4)alkoxy(C.sub.1-C.sub.4)alkyl radicals,
C.sub.1-C.sub.4 alkyl radicals substituted with an entity chosen
from nitrogenous groups, a phenyl group and a 4'-aminophenyl
group;
[0066] R.sub.19 is chosen from a hydrogen atom, C.sub.1-C.sub.4
alkyl radicals, C.sub.1-C.sub.4 monohydroxyalkyl radicals,
C.sub.2-C.sub.4 polyhydroxyalkyl radicals,
(C.sub.1-C.sub.4)alkoxy(C.sub.1-C.sub.4)alkyl radicals and
C.sub.1-C.sub.4 alkyl radicals substituted with a nitrogenous
group;
[0067] R.sub.20 is chosen from a hydrogen atom, halogen atoms such
as chlorine, bromine, iodine and fluorine atoms, C.sub.1-C.sub.4
alkyl radicals, C.sub.1-C.sub.4 monohydroxyalkyl radicals,
C.sub.1-C.sub.4 hydroxyalkoxy radicals,
acetylamino(C.sub.1-C.sub.4)alkoxy radicals, C.sub.1-C.sub.4
mesylamino-alkoxy radicals and carbamoylamino(C.sub.1-C.s-
ub.4)alkoxy radicals,
[0068] R.sub.21 is chosen from hydrogen and halogen atoms and
C.sub.1-C.sub.4 alkyl radicals.
[0069] Among the nitrogenous groups of formula (II) above, examples
include amino, mono(C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkyla- mino, tri(C.sub.1-C.sub.4)alkylamino,
monohydroxy(C.sub.1-C.sub.4)alkylami- no, imidazolinium and
ammonium radicals.
[0070] Among the para-phenylenediamines of formula (II) above,
examples include para-phenylenediamine, para-tolylenediamine,
2-chloro-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine,
2,6-dimethyl-para-phenylenediamine,
2,6-diethyl-para-phenylenediamine,
2,5-dimethyl-para-phenylenediamine,
N,N-dimethyl-para-phenylenediamine,
N,N-diethyl-para-phenylenediamine,
N,N-dipropyl-para-phenylenediamine,
4-amino-N,N-diethyl-3-methylaniline,
N,N-bis(.beta.-hydroxyethyl)-para-ph- enylenediamine,
4-amino-N,N-bis(.beta.-hydroxyethyl)-2-methylaniline,
4-amino-2-chloro-N,N-bis(.beta.-hydroxyethyl)aniline,
2-.beta.-hydroxyethyl-para-phenylenediamine,
2-fluoro-para-phenylenediami- ne,
2-isopropyl-para-phenylenediamine,
N-(.beta.-hydroxypropyl)-para-pheny- lenediamine,
2-hydroxymethyl-para-phenylenediamine,
N,N-dimethyl-3-methyl-para-phenylenediamine,
N,N-(ethyl-.beta.-hydroxyeth- yl)-para-phenylenediamine,
N-(.beta.,.gamma.-dihydroxypropyl)-para-phenyle- nediamine,
N-(4'-aminophenyl)-para-phenylenediamine,
N-phenyl-para-phenylenediamine,
2-.beta.-hydroxyethyloxy-para-phenylenedi- amine,
2-.beta.-acetylaminoethyloxy-para-phenylenediamine and
N-(.beta.-methoxyethyl)-para-phenylenediamine, and the acid
addition salts thereof.
[0071] Among the para-phenylenediamines of formula (II) above,
para-phenylenediamine, para-tolylenediamine,
2-isopropyl-para-phenylenedi- amine,
2-.beta.-hydroxyethyl-para-phenylenediamine,
2-.beta.-hydroxyethyloxy-para-phenylenediamine,
2,6-dimethyl-para-phenyle- nediamine,
2,6-diethyl-para-phenylenediamine, 2,3-dimethyl-para-phenylened-
iamine, N,N-bis(.beta.-hydroxyethyl)-para-phenylenediamine,
2-chloro-para-phenylenediamine and
2-.beta.-acetylaminoethyloxy-para-phen- ylenediamine, and the acid
addition salts thereof, are most particularly preferred.
[0072] According to the invention, the term double bases is
understood to refer to the compounds comprising at least two
aromatic rings bearing amino and/or hydroxyl groups.
[0073] Among the double bases which can be used as oxidation bases
in the dye compositions according to the invention, examples
include the compounds corresponding to formula (III) below, and the
acid addition salts thereof: 6
[0074] wherein:
[0075] Z.sub.1 and Z.sub.2, which may be identical or different,
are chosen from a hydroxyl radical and an --NH.sub.2 radical which
may be substituted with a C.sub.1-C.sub.4 alkyl radical or with a
linker arm G;
[0076] the linker arm G is chosen from linear alkylene chains
comprising from 1 to 14 carbon atoms and branched alkylene chains
comprising from 2 to 14 carbon atoms, wherein said chains may be
interrupted by or terminated with at least one nitrogenous group
and/or at least one hetero atom, such as oxygen, sulphur and
nitrogen atoms, and optionally substituted with at least one
radical chosen from hydroxyl and C.sub.1-C.sub.6 alkoxy
radicals;
[0077] R.sub.22 and R.sub.23 are chosen from hydrogen and halogen
atoms, C.sub.1-C.sub.4 alkyl radicals, C.sub.1-C.sub.4
monohydroxyalkyl radicals, C.sub.2-C.sub.4 polyhydroxyalkyl
radicals, C.sub.1-C.sub.4 aminoalkyl radicals, and a linker arm
G;
[0078] R.sub.24, R.sub.25, R.sub.26, R.sub.27, R.sub.28 and
R.sub.29, which may be identical or different, are chosen from a
hydrogen atom, a linker arm G and C.sub.1-C.sub.4 alkyl radicals;
with the proviso that the compounds of formula (III) contain only
one linker arm G per molecule.
[0079] Among the nitrogenous groups of formula (III) above,
examples include amino, mono(C.sub.1-C.sub.4)alkylamino,
di(C.sub.1-C.sub.4)alkyla- mino, tri(C.sub.1-C.sub.4)alkylamino,
monohydroxy(C.sub.1-C.sub.4)alkylami- no, imidazolinium and
ammonium radicals.
[0080] Among the double bases of formula (III) above, examples
include
N,N'-bis(.beta.-hydroxyethyl)-N,N'-bis(4'-aminophenyl)-1,3-diaminopropano-
l,
N,N'-bis(.beta.-hydroxyethyl)-N,N'-bis(4'-aminophenyl)ethylenediamine,
N,N'-bis(4-aminophenyl)-tetramethylenediamine,
N,N'-bis(.beta.-hydroxyeth-
yl)-N,N'-bis(4-aminophenyl)-tetramethylenediamine,
N,N'-bis(4-methylaminop- henyl)tetramethylenediamine,
N,N'-bis-(ethyl)-N,N'-bis(4'-amino-3'-methylp-
henyl)ethylenediamine and
1,8-bis(2,5-diaminophenoxy)-3,5-dioxaoctane, and the acid addition
salts thereof.
[0081] Among these double bases of formula (III),
N,N'-bis(.beta.-hydroxye-
thyl)-N,N'-bis(4'-aminophenyl)-1,3-diaminopropanol and
1,8-bis(2,5-diaminophenoxy)-3,5-dioxaoctane, or one of the acid
addition salts thereof, are particularly preferred.
[0082] Among the para-aminophenols which can be used as oxidation
bases in the dye compositions according to the invention, examples
include the compounds corresponding to formula (IV) below, and the
acid addition salts thereof: 7
[0083] wherein:
[0084] R.sub.30 is chosen from hydrogen and halogen atoms,
C.sub.1-C.sub.4 alkyl radicals, C.sub.1-C.sub.4 monohydroxyalkyl
radicals, (C.sub.1-C.sub.4)alkoxy(C.sub.1-C.sub.4)alkyl radicals,
C.sub.1-C.sub.4 aminoalkyl radicals, and
hydroxy(C.sub.1-C.sub.4)alkylamino(C.sub.1-C.sub- .4)alkyl
radicals,
[0085] R.sub.31 is chosen from hydrogen and halogen atoms,
C.sub.1-C.sub.4-alkyl radicals, C.sub.1-C.sub.4 monohydroxyalkyl
radicals, C.sub.2-C.sub.4 polyhydroxyalkyl radicals,
C.sub.1-C.sub.4 aminoalkyl radicals, C.sub.1-C.sub.4 cyanoalkyl
radicals, and (C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)alkyl
radicals,
[0086] with the proviso that at least one of the radicals R.sub.30
and R.sub.31 is a hydrogen atom.
[0087] Among the para-aminophenols of formula (IV) above, examples
include para-aminophenol, 4-amino-3-methylphenol,
4-amino-3-fluorophenol, 4-amino-3-hydroxymethylphenol,
4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol,
4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol,
4-amino-2-(.beta.-hydroxyethylaminomethyl)ph- enol and
4-amino-2-fluorophenol, and the acid addition salts thereof.
[0088] Among the ortho-aminophenols which can be used as oxidation
bases in the dye compositions according to the invention, examples
include 2-aminophenol, 2-amino-5-methylphenol,
2-amino-6-methylphenol and 5-acetamido-2-aminophenol, and the acid
addition salts thereof.
[0089] Among the heterocyclic bases which can be used as oxidation
bases in the dye compositions according to the invention, examples
include pyridines, pyrimidines and pyrazoles, and the acid addition
salts thereof.
[0090] Among the pyridines, preferred compounds are described, for
example, in patents GB 1,026,978 and GB 1,153,196 (the disclosures
of which are specifically incorporated by reference herein), such
as 2,5-diaminopyridine, 2-(4-methoxyphenyl)amino-3-aminopyridine,
2,3-diamino-6-methoxypyridine,
2-(.beta.-methoxy-ethyl)amino-3-amino-6-me- thoxypyridine and
3,4-diaminopyridine, and the acid addition salts thereof.
[0091] Among the pyrimidines, preferred compounds are described,
for example, in German patent DE 2,359,399 or Japanese patents JP
88-169,571 and JP 91-10659 or patent application WO 96/15765 (the
disclosures of which are specifically incorporated by reference
herein), such as 2,4,5,6-tetraaminopyrimidine,
4-hydroxy-2,5,6-triaminopyrimidine,
2-hydroxy-4,5,6-triaminopyrimidine,
2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triaminopyrimidine,
and pyrazolopyrimidine derivatives such as those mentioned in
patent application FR-A-2,750,048 (the disclosure of which is
specifically incorporated by reference herein), and examples
include pyrazolo[1,5-a]pyrimidine-3,7-diamine;
2,5-dimethylpyrazolo[1,5-a- ]pyrimidine-3,7-diamine,
pyrazolo[1,5-a]pyrimidine-3,5-diamine;
2,7-dimethylpyrazolo[1,5-a]pyrimidine-3,5-diamine,
3-aminopyrazolo[1,5-a]pyrimidin-7-ol;
3-aminopyrazolo[1,5-a]pyrimidin-5-o- l;
2-(3-aminopyrazolo[1,5-a]pyrimidin-7-ylamino)ethanol,
2-(7-aminopyrazolo[1,5-a]pyrimidin-3-ylamino)ethanol,
2-[(3-aminopyrazolo[1,5-a]pyrimidin-7-yl)(2-hydroxyethyl)amino]ethanol,
2-[(7-aminopyrazolo[1,5-a]pyrimidin-3-yl)(2-hydroxyethyl)amino]ethanol,
5,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine,
2,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine and
2,5,N7,N7-tetramethylpyrazolo[1,5-a]pyrimidine-3,7-diamine and the
addition salts and tautomeric forms thereof, when a tautomeric
equilibrium exists, and the acid addition salts thereof.
[0092] Among the pyrazoles, preferred compounds are described in
patents DE 3,843,892, DE 4,133,957 and patent applications WO
94/08969, WO 94/08970, FR-A-2,733,749 and DE 195 43 988 (the
disclosures of which are specifically incorporated by reference
herein), for example 4,5-diamino-1-methylpyrazole,
3,4-diaminopyrazole, 4,5-diamino-1-(4'-chlorobenzyl)pyrazole,
4,5-diamino-1,3-dimethyl-pyrazol- e,
4,5-diamino-3-methyl-1-phenylpyrazole,
4,5-diamino-1-methyl-3-phenylpyr- azole,
4-amino-1,3-dimethyl-5-hydrazinopyrazole,
1-benzyl-4,5-diamino-3-me- thylpyrazole,
4,5-diamino-3-tert-butyl-1-methylpyrazole,
4,5-diamino-1-tert-butyl-3-methylpyrazole,
4,5-diamino-1-(.beta.-hydroxye- thyl)-3-methylpyrazole,
4,5-diamino-1-ethyl-3-methylpyrazole,
4,5-diamino-1-ethyl-3-(4'-methoxyphenyl)pyrazole,
4,5-diamino-1-ethyl-3-h- ydroxymethylpyrazole,
4,5-diamino-3-hydroxymethyl-1-methylpyrazole,
4,5-diamino-3-hydroxymethyl-1-isopropylpyrazole,
4,5-diamino-3-methyl-1-i- sopropyl-pyrazole,
4-amino-5-(2'-aminoethyl)amino-1,3-dimethylpyrazole,
3,4,5-triaminopyrazole, 1-methyl-3,4,5-triaminopyrazole,
3,5-diamino-1-methyl-4-methylaminopyrazole and
3,5-diamino-4-(.beta.-hydr- oxyethyl)amino-1-methylpyrazole, and
the acid addition salts thereof.
[0093] The at least one oxidation base preferably is present in an
amount ranging from about 0.0005 to about 12% by weight relative to
the total weight of the dye composition according to the invention,
and even more preferably from about 0.005 to about 6% by weight
relative to this weight.
[0094] The preferred at least one cationic direct dye of formula
(I) according to the invention is chosen from:
[0095] 4'-dimethylaminophenyl-2-azopyridine N-oxide of formula:
8
[0096] 4'-dimethylamino-2'-methylphenyl-2-azopyridine N-oxide of
formula: 9
[0097]
2-[(1,3-diamino-6-methyl-4-phenyl)azo]-3-methylbenzothiazolium
iodide of formula: 10
[0098] 6'-hydroxybenzomorpholine-7'-aza-2-methyl-3-benzothiazolium
chloride of formula: 11
[0099]
6'-hydroxybenzomorpholine-7'-aza-2-methyl-4-phenyl-3-thiazolium
perchlorate of formula: 12
[0100] 6'-hydroxybenzomorpholine-7'-azo-2-diphenyl-3,4-thiazolium
perchlorate of formula: 13
[0101] 6'-hydroxybenzomorpholine-7'-aza-2-methyl-3-benzothiazolium
chloride of formula: 14
[0102]
6'-hydroxybenzomorpholine-7'-aza-2-methyl-4-phenyl-3-thiazolium
perchlorate of formula: 15
[0103] 2',4'-diamino-5'-methoxyphenyl-2-azopyridine N-oxide of
formula: 16
[0104] 2'-acetamido-4'-hydroxy-5'-methylphenyl-2-azopyridine
N-oxide of formula: 17
[0105] 2'-acetamido-4'-dimethylaminophenyl-2-azopyridine N-oxide of
formula: 18
[0106] 2'-amino-4'-dimethylaminophenyl-2-azopyridine N-oxide of
formula: 19
[0107] 2',4'-diamino-5'-methylphenyl-2-azomethoxy-1-pyridinium
perchlorate of formula: 20
[0108] 2',5'-dimethyl-4'-hydroxyphenyl-2-azopyridine N-oxide of
formula: 21
[0109] 2'-dimethylamino-4'-hydroxyphenyl-2-azopyridine N-oxide of
formula: 22
[0110] 4'-dimethylamino-2'-hydroxyphenyl-2-azopyridine N-oxide of
formula: 23
[0111] 3',5'-dimethyl-4'-hydroxyphenyl-2-azopyridine N-oxide of
formula: 24
[0112] 4'-dimethylamino-2'-nitrophenyl-2-azopyridine N-oxide of
formula: 25
[0113] 8'-hydroxyquinoline-5':2'-azopyridine N-oxide of formula:
26
[0114] 2'-nitro-4'-dimethylaminophenyl-2-azomethoxy-1-pyridinium
methosulphate of formula: 27
[0115] 4'-dimethylaminophenyl-2-azo-5-nitropyridine N-oxide of
formula: 28
[0116] 4'-dimethylaminophenyl-2-azo-6-methylpyridine N-oxide of
formula: 29
[0117] 4'-dimethylaminophenyl-2-azo-5-methylpyridine N-oxide of
formula: 30
[0118] 4'-dimethylaminophenyl-2-azo-3-methylpyridine N-oxide of
formula: 31
[0119] 4'-diethylaminophenyl-2-azo-3-methylpyridine N-oxide of
formula: 32
[0120] 4'-dimethylamino-2'-acetylaminophenyl-2-azo-3-methylpyridine
N-oxide of formula: 33
[0121] 4'-aminonaphthalene-1':2-azo-6-methylpyridine N-oxide of
formula: 34
[0122] 4'-di(.beta.-hydroxyethyl)aminophenyl-2-azo-6-methylpyridine
N-oxide of formula: 35
[0123] 4'-diethylaminophenyl-2-azo-6-methylpyridine N-oxide of
formula: 36
[0124] 2',5'-dimethyl-4'-hydroxyphenyl-2-azo-6-methylpyridine
N-oxide of formula: 37
[0125] 4'-di(.beta.-hydroxyethyl)aminophenyl-2-azo-4-methylpyridine
N-oxide of formula: 38
[0126] 4'-diethylaminophenyl-2-azo-4-methylpyridine N-oxide of
formula: 39
[0127] 4'-aminonaphthalene-1':2-azo-4-methylpyridine N-oxide of
formula: 40
[0128] 2',4'-diamino-5'-methylphenyl-2-azo-2-4-methylpyridine
N-oxide of formula: 41
[0129] 4'-dimethylaminophenyl-2-azo-4-methylpyridine N-oxide of
formula: 42
[0130] 4'-dimethylaminophenyl-2-azo-4,6-dimethylpyridine N-oxide of
formula: 43
[0131] 2',5'-dimethyl-4'-hydroxyphenyl-2-azo-4-methylpyridine
N-oxide of formula: 44
[0132] 4'-dimethylaminophenyl-2-azo-5-chloropyridine N-oxide of
formula: 45
[0133] 4'-dimethylamino-2'-methylphenyl-2-azo-5-chloropyridine
N-oxide of formula: 46
[0134] 4'-diethylaminophenyl-2-azo-5-chloropyridine N-oxide of
formula: 47
[0135] 6'-hydroxybenzomorpholine-7':2-azopyridine N-oxide of
formula: 48
[0136] 6'-hydroxybenzomorpholine-7':2-azo-1-methoxypyridinium
methosulphate of formula: 49
[0137] 2',4'-diamino-5'-methylphenyl-2-azopyridine N-oxide of
formula: 50
[0138]
2'-methyl-5'-oxo-4'-phenyldihydropyrazolyl-2-azo-1-methoxypyridiniu-
m methosulphate of formula: 51
[0139] 3'-methyl-2',4',6'-trioxohexahydropyrimidinyl-2-azopyridine
N-oxide of formula: 52
[0140] 4'-aminophenyl-2-azopyridine N-oxide of formula: 53
[0141] 4'-di(.beta.-hydroxyethyl)aminophenyl-2-azopyridine N-oxide
of formula: 54
[0142] 4'-(N-phenylamino)phenyl-2-azopyridine N-oxide of formula:
55
[0143] 4'-(N-phenylamino)phenyl-2-azo-3-methylpyridine N-oxide of
formula: 56
[0144] 4'-aminophenyl-2-azo-1,3-dimethylpyridinium methosulphate of
formula: 57
[0145]
4'-di(.beta.-hydroxyethyl)aminophenyl-2-azo-1,4-dimethylpyridinium
methosulphate of formula: 58
[0146] 4'-dimethylaminophenyl-2-azo-1,3-dimethylpyridinium
methosulphate of formula: 59
[0147] 4'-N-phenylaminophenyl-2-azo-1,6-dimethylpyridinium
methosulphate of formula: 60
[0148] 4'-dimethylaminophenyl-2-azo-1,5-dimethylpyridinium
methosulphate of formula: 61
[0149] 4'-dimethylaminophenyl-2-azo-1,6-dimethylpyridinium
methosulphate of formula: 62
[0150] 2',4',6'-trioxohexahydropyrimidinyl-2-azopyridine N-oxide of
formula: 63
[0151] 4'-dimethylaminophenyl-2-azo-1,3-dimethylbenzimidazolium
perchlorate of formula: 64
[0152] 2',4'-diamino-3'-pyridine-2-azopyridine N-oxide of formula:
65
[0153] The at least one cationic direct dye of formula (I) used
according to the invention preferably is present in an amount
ranging from about 0.001 to about 10% by weight relative to the
total weight of the dye composition, and even more preferably from
about 0.01 to about 5% by weight relative to this weight.
[0154] The dye composition according to the invention may further
comprise at least one coupler and/or at least one additional direct
dye other than the compounds of formula (I), particularly to modify
the shades or to enrich them with glints.
[0155] Among the couplers which can be present in the dye
composition according to the invention, examples include
meta-phenylenediamines, meta-aminophenols, meta-diphenols and
heterocyclic couplers, and the addition salts thereof with an
acid.
[0156] When they are present, the at least one coupler preferably
is present in an amount ranging from about 0.0001 to about 10% by
weight relative to the total weight of the dye composition, and
even more preferably from about 0.005 to about 5% by weight
relative to this weight.
[0157] In general, the preferred addition salts with an acid which
can be used in the context of the dye compositions of the invention
(oxidation bases and couplers) are the hydrochlorides,
hydrobromides, sulphates, tartrates, lactates and acetates.
[0158] The medium suitable for dyeing (or support) for the dye
composition according to the invention generally comprises water or
a mixture of water and at least one organic solvent to dissolve the
compounds which would not be sufficiently water-soluble. Examples
include C.sub.1-C.sub.4 alkanols, such as ethanol and isopropanol,
as organic solvents.
[0159] The solvents can be present in proportions preferably
ranging from about 1 to about 40% by weight relative to the total
weight of the dye composition, and even more preferably from about
5 to about 30% by weight.
[0160] The pH of the dye composition according to the invention
generally ranges from about 3 to about 12, and preferably from
about 5 to about 12. The pH can be adjusted to the desired value by
means of acidifying or basifying agents usually used for dyeing
keratin fibres.
[0161] Representative acidifying agents include organic or
inorganic acids such as hydrochloric acid, orthophosphoric acid,
sulphuric acid, carboxylic acids such as acetic acid, tartaric
acid, citric acid and lactic acid, and sulphonic acids.
[0162] Representative basifying agents include aqueous ammonia,
alkaline carbonates, alkanolamines such as mono-, di- and
triethanolamine, 2-methyl-2-aminopropanol and derivatives thereof,
sodium hydroxide, potassium hydroxide and the compounds of formula
(IX) below: 66
[0163] wherein W is a propylene residue optionally substituted with
a hydroxyl group or a C.sub.1-C.sub.4 alkyl radical; R.sub.32,
R.sub.33, R.sub.34 and R.sub.35, which may be identical or
different, are chosen from a hydrogen atom and C.sub.1-C.sub.4
alkyl and C.sub.1-C.sub.4 hydroxyalkyl radicals.
[0164] The dye composition according to the invention can also
contain various adjuvants conventionally used in compositions for
dyeing the hair.
[0165] Needless to say, a person skilled in the art will take care
to select this or these optional complementary compounds such that
the advantageous properties intrinsically associated with the dye
composition according to the invention are not, or are not
substantially, adversely affected by the addition(s) envisaged.
[0166] The dye composition according to the invention can be in
various forms, such as in the form of liquids, creams or gels,
which may be pressurized, or in any other form suitable for dyeing
keratin fibres, particularly human hair.
[0167] Another subject of the invention is a process for dyeing
keratin fibres, especially human keratin fibres such as the hair,
using the dye composition as defined above.
[0168] According to this process, the dye composition as defined
above is applied to the fibres, the colour being developed at
acidic, neutral or alkaline pH by means of an oxidizing agent added
to the dye composition just at the time of use, or which is present
in an oxidizing composition applied simultaneously or sequentially
in a separate manner.
[0169] According to one particularly preferred embodiment of the
dyeing process according to the invention, the dye composition
described above is mixed, at the time of use, with an oxidizing
composition containing, in a medium suitable for dyeing, at least
one oxidizing agent present in an amount sufficient to develop a
coloration. The mixture obtained is then applied to the keratin
fibres and is left on the fibres for about 3 to about 50 minutes,
preferably for about 5 to about 30 minutes, after which the fibres
are rinsed, washed with shampoo, rinsed again and dried.
[0170] The oxidizing agent present in the oxidizing composition as
defined above can be chosen from the oxidizing agents
conventionally used for the oxidation dyeing of keratin fibres,
such as, for example, hydrogen peroxide, urea peroxide, alkali
metal bromates, persalts such as perborates and persulphates,
peracids, and enzymes such as 2-electron oxidoreductases,
peroxidases and lactases. Hydrogen peroxide is particularly
preferred.
[0171] 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 fibres preferably ranges from about 3 to about 12 and even
more preferably from about 5 to about 11. The pH is adjusted to the
desired value by means of acidifying or basifying agents usually
used for dyeing keratin fibres and as defined above.
[0172] The oxidizing composition as defined above can also contain
various adjuvants conventionally used in compositions for dyeing
the hair.
[0173] The composition that is finally applied to the keratin
fibres can be in various forms, such as in the form of liquids,
creams or gels or in any other form suitable for dyeing keratin
fibres, particularly human hair.
[0174] Another subject of the invention is a multi-compartment
dyeing device or "kit" or any other multi-compartment packaging
system, a first compartment comprising the dye composition as
defined above and a second compartment comprising the oxidizing
composition as defined above. These devices can be equipped with
means for delivering the desired mixture onto the hair, such as the
devices described in patent FR-2,586,913, in the name of the
L'Oral, the disclosure of which is specifically incorporated by
reference herein.
[0175] The present invention is further illustrated by the
following examples which are designed to teach those of ordinary
skill in the art how to practice the invention. The following
examples are intended to illustrate the invention without limiting
its scope.
EXAMPLES
Dyeing Examples 1 to 4
[0176] The dye compositions below, according to the invention, were
prepared (contents in grams):
1 EXAMPLE 1 2 3 4 4'-Dimethylaminophenyl-2-a- zopyridine N- 0.5 --
4.0 -- oxide (compound of formula (I))
4'-Dimethylaminophenyl-2-azo-1,3- -- 0.5 -- 4.0 dimethylpyridinium
methosulphate (compound of formula (I)) para-Phenylenediamine
(oxidation base) 0.324 0.324 0.324 0.324 5-Amino-2-methylphenol
(coupler) 0.369 -- 0.369 -- meta-Aminophenol (coupler) -- 0.327 --
0.327 Common dye support (*) (*) (*) (*) Demineralized water qs 100
g 100 g 100 g 100 g (*): Common dye support: Oleyl alcohol
polyglycerolated 4.0 g with 2 mol of glycerol Oleyl alcohol
polyglycerolated with 5.69 g A.M. 4 mol of glycerol, containing 78%
active material (A.M.) Oleic acid 3.0 g Oleylamine containing 2 mol
of 7.0 g ethylene oxide, sold under the trade name Ethomeen O12
.RTM. by the company Akzo Diethylaminopropyl 3.0 g A.M.
laurylaminosuccinamate, sodium salt, containing 55% A.M. Oleyl
alcohol 5.0 g Oleic acid diethanolamide 12.0 g Propylene glycol 3.5
g Ethyl alcohol 16.5 g Sodium metabisulphite as an aqueous 0.455 g
A.M. solution containing 35% A.M. Ammonium acetate 0.8 g
Antioxidant, sequestering agent q.s. Fragrance, preserving agent
q.s. Aqueous ammonia containing 20% NH.sub.3 10.0 g
[0177] Each of the dye compositions described above was mixed, at
the time of use, with an equivalent amount by weight of 20-volumes
hydrogen peroxide (6% by weight) with a pH of about 3.
[0178] Each resulting mixture had a pH of about 10.+-.0.2 and was
applied for 30 minutes to locks of grey hair containing 90%
permanent-waved white hairs.
[0179] The locks were then rinsed with water, washed with a
standard shampoo, rinsed again and then dried.
[0180] The hair was dyed in the shades featured in the table
below:
2 EXAMPLE SHADE OBTAINED 1 Intense red 2 Intense purple 3 Intense
red 4 Intense purple
[0181] The foregoing written description relates to various
embodiments of the present invention. Numerous changes and
modifications may be made therein without departing from the spirit
and scope of the invention as defined in the following claims.
* * * * *