U.S. patent application number 09/321889 was filed with the patent office on 2002-01-17 for dye composition for keratin fibers, with a cationic direct dye and a polyol or polyol ether.
This patent application is currently assigned to L' OREAL S.A.. Invention is credited to COTTERET, JEAN, LANG, GERARD.
Application Number | 20020004955 09/321889 |
Document ID | / |
Family ID | 9526825 |
Filed Date | 2002-01-17 |
United States Patent
Application |
20020004955 |
Kind Code |
A1 |
LANG, GERARD ; et
al. |
January 17, 2002 |
DYE COMPOSITION FOR KERATIN FIBERS, WITH A CATIONIC DIRECT DYE AND
A POLYOL OR POLYOL ETHER
Abstract
The invention relates to a dye composition for keratin fibers,
in particular for human keratin fibers such as the hair, comprising
at least one cationic direct dye of given formula and at least
glycerol and/or one specific polyol and/or polyol ether. The
invention also relates to the dyeing processes and devices using
this composition.
Inventors: |
LANG, GERARD; (SAINT PRIX,
FR) ; COTTERET, JEAN; (VERNEUIL SUR SEINE,
FR) |
Correspondence
Address: |
FINNEGAN HENDERSON FARABOW GARRETT &
DUNNER LLP
1300 I STREET NW
WASHINGTON
DC
200053315
|
Assignee: |
L' OREAL S.A.
|
Family ID: |
9526825 |
Appl. No.: |
09/321889 |
Filed: |
May 28, 1999 |
Current U.S.
Class: |
8/405 ; 8/406;
8/407; 8/426 |
Current CPC
Class: |
A61K 8/49 20130101; A61K
8/4946 20130101; A61K 8/494 20130101; A61K 8/4926 20130101; A61Q
5/065 20130101 |
Class at
Publication: |
8/405 ; 8/406;
8/407; 8/426 |
International
Class: |
A61K 007/13 |
Foreign Application Data
Date |
Code |
Application Number |
May 28, 1998 |
FR |
98 06752 |
Claims
What is claimed is:
1. A composition for dyeing keratin fibers comprising: (i) at least
one cationic direct dye of formula (I) below:A--N.dbd.N--B (I)in
which: the symbol A represents a group chosen from structures
A.sub.1 to A.sub.3 below: 7in which structures A.sub.1 to A.sub.3,
R.sub.1 is chosen from C.sub.1-C.sub.4 alkyl radicals and a phenyl
radical 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, in the case of structure A.sub.1, can together
form a substituted benzene ring, and in the case of structure
A.sub.2, can together form a benzene ring optionally having at
least one substituent chosen from C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 alkoxy and NO.sub.2 radicals; R.sub.3 can also
denote a hydrogen atom; Z is chosen from an oxygen atom, a sulphur
atom, and --NR.sub.2 groups; M is chosen from --CH, --CR, where R
is chosen from C.sub.1-C.sub.4 alkyl radicals, and
--N.sup.+R.sub.5(X.sup.-).sub.r groups; K is chosen from --CH,
--CR, where R is chosen from C.sub.1-C.sub.4 alkyl radicals, and
--N.sup.+R.sub.5(X.sup.-).sub.r groups; P is chosen from --CH,
--CR, where R is chosen from C.sub.1-C.sub.4 alkyl radicals, and
--N.sup.+R.sub.5(X.sup.+).sub.r groups; r denotes 0 or 1; R.sub.5
is chosen from an atom O.sup.-, C.sub.1-C.sub.4 alkoxy radicals and
C.sub.1-C.sub.4 alkyl radicals; R.sub.6 and R.sub.7, 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
an --NO.sub.2 radical; X.sup.- is an anion; with the proviso that,
if R.sub.4 is a C.sub.1-C.sub.4 alkyl radical and Z is a sulphur
atom, R.sub.3 is not a hydrogen atom; if R.sub.5 is O.sup.-, then r
is zero; if K or P or M is --N.sup.+--C.sub.1-C.sub.4 -alkyl
X.sup.-, then R.sub.6 or R.sub.7 is other than a hydrogen atom; if
K is --N.sup.+R.sub.5(X.sup.-).sub.r, then M.dbd.P and is --CH or
--CR; if M is --N.sup.+R.sub.5(X.sup.-).sub.r, then K.dbd.P and is
--CH or --CR; if P is --N.sup.+R.sub.5(X.sup.-).sub.r- , then
K.dbd.M and is --CH or --CR; if Z is --NR.sub.2 and 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.3 or R.sub.4 of structure A.sub.2 is other than a
C.sub.1-C.sub.4 alkyl radical; the symbol B represents: (a) a group
of structure B.sub.1 below: 8in which structure B.sub.1, R.sub.8 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 radical --OH, a radical
--NO.sub.2, --NHR.sub.11 radicals, --NR.sub.12R.sub.13 radicals,
and --NHCO(C.sub.1-C.sub.4)alkyl radicals or forms, with R.sub.9, a
5- or 6-membered ring which may contain at least one hetero atom
chosen from nitrogen, oxygen and sulphur; R.sub.9 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.10 or R.sub.11, a 5- or
6-membered ring which may contain at least one hetero atom chosen
from nitrogen, oxygen and sulphur; R.sub.10 is chosen from a
hydrogen atom, an --OH radical, --NHR.sub.11 radicals and
--NR.sub.12R.sub.13 radicals; R.sub.11 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.12 and R.sub.13, 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; or (b) a 5- or
6-membered nitrogenous heterocyclic group which can contain at
least one other hetero atom and/or at least one carbonyl group and
which can have at least one substituent chosen from C.sub.1-C.sub.4
alkyl, amino and phenyl radicals, and (ii) at least one compound
chosen from glycerol, polyols containing at least 4 carbon atoms,
C.sub.1-C.sub.8 aliphatic ethers of C.sub.3-C.sub.9 polyols, and
C.sub.6-C.sub.8 aromatic ethers of C.sub.2-C.sub.9 polyols.
2. The composition according to claim 1, wherein, in formula (I),
the C.sub.1-C.sub.4 alkyl radicals are chosen from methyl, ethyl,
and butyl radicals and the C.sub.1-C.sub.4 alkoxy radicals are
methoxy and ethoxy radicals.
3. The composition according to claim 1, wherein the symbol B
represents a a group of structure B.sub.2 below: 9in which
structure B.sub.2, R.sub.14 and R.sub.15, which may be identical or
different, are chosen from a hydrogen atom, C.sub.1-C.sub.4 alkyl
radicals and a phenyl radical; Y is chosen from a --CO-- radical
and a radical 10n=0 or 1, where, when n is 1, U is a --CO--
radical.
4. The composition according to claim 1, wherein X.sup.- is chosen
from chloride, iodide, methyl sulphate, ethyl sulphate, acetate and
perchlorate.
5. The composition according to claim 1, wherein said keratin
fibers are human keratin fibers.
6. The composition according to claim 5, wherein said human keratin
fibers are hair.
7. The composition according to claim 1, wherein said polyols
containing at least 4 carbon atoms are chosen from C.sub.4-C.sub.9
polyols and polyalkylene glycols.
8. The composition according to claim 7, wherein said polyalkylene
glycols are chosen from polyethylene glycols and polypropylene
glycols.
9. The composition according to claim 7, wherein said
C.sub.4-C.sub.9 polyols are chosen from 2-butene-1,4-diol
pentane-1,5-diol, 2,2-dimethylpropane-1,3-diol,
3-methylpentane-1,5-diol, pentane-1,2-diol,
2,2,4-trimethylpentane-1,3-diol, 2-methylpropane-1,3-diol, hexylene
glycol, 1,3-butylene glycol, dipropylene glycol, diethylene glycol
and triethylene glycol.
10. The composition according to claim 1, wherein said
C.sub.1-C.sub.8 aliphatic ethers of C.sub.3-C.sub.9 polyols are
chosen from propylene glycol monomethyl ether, propylene glycol
monoethyl ether, isopropylene glycol dimethyl ether, diethylene
glycol monomethyl ether and monoethyl ether, dipropylene glycol
monomethyl ether, tripropylene glycol monomethyl ether and
diethylene glycol dimethyl ether.
11. The composition according to claim 1, wherein said
C.sub.6-C.sub.8 aromatic ethers of C.sub.2-C.sub.9 polyols are
chosen from ethylene glycol monophenyl ether, ethylene glycol
monobenzyl ether, propylene glycol monophenyl ether, propylene
glycol monobenzyl ether, diethylene glycol monophenyl ether and
diethylene glycol monobenzyl ether.
12. The composition according to claim 1, wherein said at least one
cationic direct dye is chosen from structures (I).sub.1 to
(I).sub.77 below: 11
13. The composition according to claim 1, wherein said at least one
cationic direct dye of formula (I) is present in an amount ranging
from 0.001 to 10% by weight relative to the total weight of the
composition.
14. The composition according to claim 13, wherein said at least
one cationic direct dye of formula (I) is present in an amount
ranging from 0.005 to 5% by weight relative to the total weight of
the composition.
15. The composition according to claim 1, wherein said at least one
compound chosen from glycerol, polyols containing at least 4 carbon
atoms, C.sub.1-C.sub.8 aliphatic, ethers of C.sub.3-C.sub.9 polyols
and C.sub.6-C.sub.8 aromatic ethers of C.sub.2-C.sub.9 polyols is
present in an amount ranging from 0.1 to 40% by weight relative to
the total weight of the composition.
16. The composition according to claim 15, wherein said at least
one compound is present in an amount ranging from 0.5 to 20% by
weight relative to the total weight of the composition.
17. The composition according to claim 1, wherein said composition
further comprises additional direct dyes.
18. The composition according to claim 1, wherein said composition
further comprises a mixture of water and at least one solvent
chosen from glycerol, polyols containing at least 4 carbon atoms,
C.sub.1-C.sub.8 aliphatic ethers of C.sub.3-C.sub.8 polyols, and
C.sub.6-C.sub.8 aromatic ethers of C.sub.2-C.sub.9 polyols.
19. The composition according to claim 18, wherein said composition
further comprises at least one additional organic solvent.
20. The composition according to claim 1, wherein said composition
has a pH ranging from 2 to 11.
21. The composition according to claim 20, wherein said pH ranges
from 5 to 10.
22. The composition according to claim 1, wherein said composition
further comprises at least one oxidation base chosen from
para-phenylenediamines, bis(pheniyl)alkylenediamines,
para-aminophenols, ortho-aminophenols and heterocyclic bases.
23. The composition according to claim 22, wherein said at least on
e oxidation base is present in an amount ranging from 0.0005 to 12%
by weight relative to the total weight of the composition.
24. The composition according to claim 23, wherein said at least
one oxidation base is present in an amount ranging from 0.005 to 6%
by weight relative to the total weight of the composition.
25. The composition according to claim 22, wherein said composition
further comprises at least one coupler chosen from
meta-phenylenediamine, meta-aminophenols, meta-diphenols and
heterocyclic couplers.
26. The composition according to claim 25, wherein said at least
one coupler is present in an amount ranging from 0.0001 to 10% by
weight relative to the total weight of the composition.
27. The composition according to claim 26, wherein said at least
one coupler is present in an amount ranging from 0.005 to 5% by
weight relative to the total weight of the composition.
28. The composition according to claim 1, wherein said composition
further comprises at least one oxidizing agent.
29. A process for dyeing keratin fibers, comprising applying to
said fibers, for a period which is sufficient to develop the
desired coloration, at least one dye composition comprising: (i) at
least one cationic direct dye of formula (I) below:A--N.dbd.N--B
(I)in which: the symbol A represents a group chosen from structures
A.sub.1 to A.sub.3 below: 12in which structures A.sub.1 to A.sub.3,
R.sub.1 is chosen from C.sub.1-C.sub.4 alkyl radicals and a phenyl
radical 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, in the case of structure A.sub.1, can together
form a substituted benzene ring, and in the case of structure
A.sub.2, can together form a benzene ring optionally having at
least one substituent chosen from C.sub.1-C.sub.4 alkyl,
C.sub.1-C.sub.4 alkoxy and NO.sub.2 radicals; R.sub.3 can also
denote a hydrogen atom; Z is chosen from an oxygen atom, a sulphur
atom, and --NR.sub.2 groups; M is chosen from --CH, --CR, where R
is chosen from C.sub.1-C.sub.4 alkyl radicals, and
--N.sup.+R.sub.5(X.sup.-).sub.r groups; K is chosen from --CH,
--CR, where R is chosen from C.sub.1-C.sub.4 alkyl radicals, and
--N.sup.+R.sub.5(X.sup.-).sub.r groups; P is chosen from --CH,
--CR, where R is chosen from C.sub.1-C.sub.4 alkyl radicals, and
--N.sup.+R.sub.5(X.sup.-).sub.r groups; r denotes 0 or 1; R.sub.5
is chosen from an atom O.sup.-, C.sub.1-C.sub.4 alkoxy radicals and
C.sub.1-C.sub.4 alkyl radicals; R.sub.6 and R.sub.7, 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
an --NO.sub.2 radical; X.sup.- is an anion; with the proviso that,
if R.sub.4 is a C.sub.1-C.sub.4 alkyl radical and Z is a sulphur
atom, R.sub.3 is not a hydrogen atom; if R.sub.5 is O.sup.-, then r
is zero; if K or P or M is --N.sup.+C.sub.1-C.sub.4 -alkyl X.sup.-,
then R.sub.6 or R.sub.7 is other than a hydrogen atom; if K is
--N.sup.+R.sub.5(X.sup.-).sub.r, then M.dbd.P and is --CH or --CR;
if M is --N.sup.+R.sub.5(X.sup.-).sub.r, then K.dbd.P and is --CH
or --CR; if P is --N.sup.+R.sub.5(X.sup.-).sub.r- , then K.dbd.M
and is --CH or --CR; if Z is --NR.sub.2 and 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.3 or R.sub.4 of structure A.sub.2 is other than a
C.sub.1-C.sub.4 alkyl radical; the symbol B represents: (a) a group
of structure B.sub.1 below: 13in which structure B.sub.1, R.sub.8
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 radical --OH, a radical
--NO.sub.2, --NHR.sub.11 radicals, --NR.sub.12R.sub.13 radicals,
and --NHCO(C.sub.1-C.sub.4)alkyl radicals or forms, with R.sub.9, a
5- or 6-membered ring which may contain at least one hetero atom
chosen from nitrogen, oxygen and sulphur; R.sub.9 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.10 or R.sub.11, a 5- or
6-membered ring which may contain at least one hetero atom chosen
from nitrogen, oxygen and sulphur; R.sub.10 is chosen from a
hydrogen atom, an --OH radical, --NHR.sub.11 radicals and
--NR.sub.12R.sub.13 radicals; R.sub.11 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.12 and R.sub.13, 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; or (b) a 5- or
6-membered nitrogenous heterocyclic group which can contain at
least one other hetero atom and/or at least one carbonyl group and
which can have at least one substituent chosen from C.sub.1-C.sub.4
alkyl, amino and phenyl radicals, and (ii) at least one compound
chosen from glycerol, polyols containing at least 4 carbon atoms,
C.sub.1-C.sub.8 aliphatic ethers of C.sub.3-C.sub.9 polyols, and
C.sub.6-C.sub.8 aromatic ethers of C.sub.2-C.sub.9 polyols, rinsing
the fibers, optionally washing said fibers with shampoo and rinsing
again, and drying.
30. A process for dyeing keratin fibers according to claim 29,
wherein said keratin fibers are human keratin fibers.
31. A process for dyeing keratin fibers according to claim 30,
wherein said human keratin fibers are hair.
32. A process for dyeing keratin fibers according to claim 29,
wherein said fibers are not rinsed a second time before drying.
33. A process for dyeing keratin fibers comprising: separately
storing a first composition comprising: (i) at least one cationic
direct dye of formula (I) below:A--N.dbd.N--B (I)in which: the
symbol A represents a group chosen from structures A.sub.1 to
A.sub.3 below: 14in which structures A.sub.1 to A.sub.3, R.sub.1 is
chosen from C.sub.1-C.sub.4 alkyl radicals and a phenyl radical
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, in the case of structure A.sub.1, can together form a
substituted benzene ring, and in the case of structure A.sub.2, can
together form a benzene ring optionally having at least one
substituent chosen from C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
alkoxy and NO.sub.2 radicals; R.sub.3 can also denote a hydrogen
atom; Z is chosen from an oxygen atom, a sulphur atom, and
--NR.sub.2 groups; M is chosen from --CH, --CR, where R is chosen
from C.sub.1-C.sub.4 alkyl radicals, and
--N.sup.+R.sub.5(X.sup.-).sub.r groups; K is chosen from --CH,
--CR, where R is chosen from C.sub.1-C.sub.4 alkyl radicals, and
--N.sup.+R.sub.5(X.sup.-).sub.r groups; P is chosen from --CH,
--CR, where R is chosen from C.sub.1-C.sub.4 alkyl radicals, and
--N.sup.+R.sub.5(X.sup.-).sub.r groups; r denotes 0 or 1; R.sub.5is
chosen from an atom O.sup.-, C.sub.1-C.sub.4 alkoxy radicals and
C.sub.1-C.sub.4 alkyl radicals; R.sub.6 and R.sub.7, 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
an --NO.sub.2 radical; X.sup.- is an anion; with the proviso that,
if R.sub.4is a C.sub.1-C.sub.4 alkyl radical and Z is a sulphur
atom, R.sub.3is not a hydrogen atom; if R.sub.5 is O.sup.-, then r
is zero; if K or P or M is --N.sup.+-C.sub.1-C.sub.4 -alkyl
X.sup.-, then R.sub.6 or R.sub.7 is other than a hydrogen atom; if
K is --N.sup.+R.sub.5(X.sup.-).sub.r, then M.dbd.P and is --CH or
--CR; if M is --N.sup.+R.sub.5(X.sup.-).sub.r, then K.dbd.P and is
--CH or --CR; if P is --N.sup.+R.sub.5(X.sup.-).sub.r- , then
K.dbd.M and is --CH or --CR; if Z is --NR.sub.2 and 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.3 or R.sub.4 of structure A.sub.2 is other than a
C.sub.1-C.sub.4 alkyl radical; the symbol B represents: (a) a group
of structure B.sub.1 below: 15in which structure B.sub.1, R.sub.8
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 radical --OH, a radical
--NO.sub.2, --NHR.sub.11 radicals, --NR.sub.12R.sub.13 radicals,
and --NHCO(C.sub.1-C.sub.4)alkyl radicals or forms, with R.sub.9, a
5- or 6-membered ring which may contain at least one hetero atom
chosen from nitrogen, oxygen and sulphur; R.sub.9 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.10 or R.sub.11, a 5- or
6-membered ring which may contain at least one hetero atom chosen
from nitrogen, oxygen and sulphur; R.sub.10 is chosen from a
hydrogen atom, an --OH radical, --NHR.sub.11 radicals and
--NR.sub.12R.sub.13 radicals; R.sub.11 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.12 and R.sub.13, 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; or (b) a 5- or
6-membered nitrogenous heterocyclic group which can contain at
least one other hetero atom and/or at least one carbonyl group and
which can have at least one substituent chosen from C.sub.1-C.sub.4
alkyl, amino and phenyl radicals, (ii) at least one compound chosen
from glycerol, polyols containing at least 4 carbon atoms,
C.sub.1-C.sub.8 aliphatic ethers of C.sub.3-C.sub.9 polyols, and
C.sub.6-C.sub.8 aromatic ethers of C.sub.2-C.sub.9 polyols, and
(iii) at least one oxidation base, separately storing a second
composition comprising at least one oxidizing agent, and thereafter
mixing said first composition with said second composition and
applying this mixture to said keratin fibers.
34. A process for dyeing keratin fibers comprising: separately
storing a first composition comprising (i) at least one cationic
direct dye of formula (I) below:A--N.dbd.N--B (I)in which: the
symbol A represents a group chosen from structures A.sub.1 to
A.sub.3 below: 16in which structures A.sub.1 to A.sub.3, R.sub.1 is
chosen from C.sub.1-C.sub.4 alkyl radicals and a phenyl radical
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, in the case of structure A.sub.1, can together form a
substituted benzene ring, and in the case of structure A.sub.2, can
together form a benzene ring optionally having at least one
substituent chosen from C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
alkoxy and NO.sub.2 radicals; R.sub.3 can also denote a hydrogen
atom; Z is chosen from an oxygen atom, a sulphur atom, and
--NR.sub.2 groups; M is chosen from --CH, --CR, where R is chosen
from C.sub.1-C.sub.4 alkyl radicals, and
--N.sup.+R.sub.5(X.sup.-).sub.r groups; K is chosen from --CH,
--CR, where R is chosen from C.sub.1-C.sub.4 alkyl radicals, and
--N.sup.+R.sub.5(X.sup.-).sub.r groups; P is chosen from --CH,
--CR, where R is chosen from C.sub.1-C.sub.4 alkyl radicals, and
--N.sup.+R.sub.5(X.sup.-).sub.r groups; r denotes 0 or 1; R.sub.5
is chosen from an atom O.sup.-, C.sub.1-C.sub.4 alkoxy radicals and
C.sub.1-C.sub.4 alkyl radicals; R.sub.6 and R.sub.7, 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
an --NO.sub.2 radical; X.sup.- is an anion; with the proviso that,
if R.sub.4 is a C.sub.1-C.sub.4 alkyl radical and Z is a sulphur
atom, R.sub.3 is not a hydrogen atom; if R.sub.5 is O.sup.-, then r
is zero; if K or P or M is --N.sup.+-C.sub.1-C.sub.4 -alkyl
X.sup.-, then R.sub.6 or R.sub.7 is other than a hydrogen atom; if
K is --N.sup.+R.sub.5(X.sup.-).sub.r, then M.dbd.P and is --CH or
--CR; if M is --N.sup.+R.sub.5(X.sup.-).sub.r, then K.dbd.P and is
--CH or --CR; if P is --N.sup.+R.sub.5(X.sup.-).sub.r- , then
K.dbd.M and is --CH or --CR; if Z is --NR.sub.2 and 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.3 or R.sub.4 of structure A.sub.2 is other than a
C.sub.1-C.sub.4 alkyl radical; the symbol B represents: (a) a group
of structure B.sub.1 below: 17in which structure B.sub.1, R.sub.8
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 radical --OH, a radical
--NO.sub.2, --NHR.sub.11 radicals, --NR.sub.12R.sub.13 radicals,
and --NHCO(C.sub.1-C.sub.4)alkyl radicals or forms, with R.sub.9, a
5- or 6-membered ring which may contain at least one hetero atom
chosen from nitrogen, oxygen and sulphur; R.sub.9 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.10 or R.sub.11, a 5- or
6-membered ring which may contain at least one hetero atom chosen
from nitrogen, oxygen and sulphur; R.sub.10 is chosen from a
hydrogen atom, an --OH radical, --NHR.sub.11 radicals and
--NR.sub.12R.sub.13 radicals; R.sub.11 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.12 and R.sub.13, 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; or (b) a 5- or
6-membered nitrogenous heterocyclic group which can contain at
least one other hetero atom and/or at least one carbonyl group and
which can have at least one substituent chosen from C.sub.1-C.sub.4
alkyl, amino and phenyl radicals, and (ii) at least one compound
chosen from glycerol, polyols containing at least 4 carbon atoms,
C.sub.1-C.sub.8 aliphatic ethers of C.sub.3-C.sub.9 polyols, and
C.sub.6-C.sub.8 aromatic ethers of C.sub.2-C.sub.9 polyols,
separately storing a second composition comprising at least one
oxidizing agent, and thereafter mixing said first composition with
said second composition and applying this mixture to said keratin
fibers.
35. A multi-compartment dyeing device or multi-compartment dyeing
kit compnsing at least two separate compartments, wherein a first
compartment contains a com position comprising: in which: the
symbol A represents a group chosen from structures A.sub.1 to
A.sub.3 below: 18in which structures A.sub.1 to A.sub.3, R.sub.1 is
chosen from C.sub.1-C.sub.4 alkyl radicals and a phenyl radical
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, in the case of structure A.sub.1, can together form a
substituted benzene ring, and in the case of structure A.sub.2, can
together form a benzene ring optionally having at least one
substituent chosen from C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
alkoxy and NO.sub.2 radicals; R.sub.3 can also denote a hydrogen
atom; Z is chosen from an oxygen atom, a sulphur atom, and
--NR.sub.2 groups; M is chosen from --CH, --CR, where R is chosen
from C.sub.1-C.sub.4 alkyl radicals, and
--N.sup.+R.sub.5(X.sup.-).sub.r groups; K is chosen from --CH,
--CR, where R is chosen from C.sub.1-C.sub.4 alkyl radicals, and
--N.sup.+R.sub.5(X.sup.-).sub.r groups; P is chosen from --CH,
--CR, where R is chosen from C.sub.1-C.sub.4 alkyl radicals, and
--N.sup.+R.sub.5(X.sup.-).sub.r groups; r denotes 0 or 1; R.sub.5
is chosen from an atom O.sup.-, C.sub.1-C.sub.4 alkoxy radicals and
C.sub.1-C.sub.4 alkyl radicals; R.sup.6 and R.sub.7, 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
an --NO.sub.2 radical; X.sup.- is an anion; with the proviso that,
if R.sub.4 is a C.sub.1-C.sub.4 alkyl radical and Z is a sulphur
atom, R.sub.3 is not a hydrogen atom; if R.sub.5 is O.sup.-, then r
is zero; if K or P or M is --N.sup.+-C.sub.1-C.sub.4 -alkyl
X.sup.-, then R.sub.6 or R.sub.7 is other than a hydrogen atom; if
K is --N.sup.+R.sub.5(X.sup.-).sub.r, then M.dbd.P and is --CH or
--CR; if M is --N.sup.+R.sub.5(X.sup.-).sub.r, then K.dbd.P and is
--CH or --CR; if P is --N.sup.+R.sub.5(X.sup.-).sub.r- , then
K.dbd.M and is --CH or --CR; if Z is --NR.sub.2 and 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.3 or R.sub.4 of structure A.sub.2 is other than a
C.sub.1-C.sub.4 alkyl radical; the symbol B represents: (a) a group
of structure B.sub.1 below: 19in which structure B.sub.1, R.sub.8
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 radical --OH, a radical
--NO.sub.2, --NHR.sub.11 radicals, --NR.sub.12R.sub.13 radicals,
and --NHCO(C.sub.1-C.sub.4)alkyl radicals or forms, with R.sub.9, a
5- or 6-membered ring which may contain at least one hetero atom
chosen from nitrogen, oxygen and sulphur; R.sub.9 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.10 or R.sub.11, a 5- or
6-membered ring which may contain at least one hetero atom chosen
from nitrogen, oxygen and sulphur; R.sub.10 is chosen from a
hydrogen atom, an --OH radical, --NHR.sub.11 radicals and
--NR.sub.12R.sub.13 radicals; R.sub.11 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.12 and R.sub.13, 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; or (b) a 5- or
6-membered nitrogenous heterocyclic group which can contain at
least one other hetero atom and/or at least one carbonyl group and
which can have at least one substituent chosen from C.sub.1-C.sub.4
alkyl, amino and phenyl radicals, (ii) at least one compound chosen
from glycerol, polyols containing at least 4 carbon atoms,
C.sub.1-C.sub.8 aliphatic ethers of C.sub.3-C.sub.9 polyols, and
C.sub.6-C.sub.8 aromatic ethers of C.sub.2-C.sub.9 polyols, and
(iii) at least one oxidation base, and a second compartment
contains a composition comprising at least one oxidizing agent.
36. A multi-compartment dyeing device or multi-compartment dyeing
kit comprising at least two separate compartments wherein a first
compartment contains a composition comprising: in which: the symbol
A represents a group chosen from structures A.sub.1 to A.sub.3
below: 20in which structures A.sub.1 to A.sub.3, R.sub.1 is chosen
from C.sub.1-C.sub.4 alkyl radicals and a phenyl radical 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,
in the case of structure A.sub.1, can together form a substituted
benzene ring, and in the case of structure A.sub.2, can together
form a benzene ring optionally having at least one substituent
chosen from C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 alkoxy and
NO.sub.2 radicals; R.sub.3 can also denote a hydrogen atom; Z is
chosen from an oxygen atom, a sulphur atom, and --NR.sub.2 groups;
M is chosen from --CH, --CR, where R is chosen from C.sub.1-C.sub.4
alkyl radicals, and --N.sup.+R.sub.5(X.sup.-).sub.r groups; K is
chosen from --CH, --CR, where R is chosen from C.sub.1-C.sub.4
alkyl radicals, and --N.sup.+R.sub.5(X.sup.-).sub.r groups; P is
chosen from --CH, --CR, where R is chosen from C.sub.1-C.sub.4
alkyl radicals, and --N.sup.+R.sub.5(X.sup.-).sub.r groups; r
denotes 0 or 1; R.sub.5 is chosen from an atom O.sup.-,
C.sub.1-C.sub.4 alkoxy radicals and C.sub.1-C.sub.4 alkyl radicals;
R.sub.6 and R.sub.7, 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 an --NO.sub.2 radical; X.sup.-
is an anion; with the proviso that, if R.sub.4 is a C.sub.1-C.sub.4
alkyl radical and Z is a sulphur atom, R.sub.3 is not a hydrogen
atom; if R.sub.5 is O.sup.-, then r is zero; if K or P or M is
--N.sup.+C.sub.1-C.sub.4 -alkyl X.sup.-, then R.sub.6 or R.sub.7 is
other than a hydrogen atom; if K is
--N.sup.+R.sub.5(X.sup.-).sub.r, then M.dbd.P and is --CH or --CR;
if M is --N.sup.+R.sub.5(X.sup.-).sub.r, then K.dbd.P and is --CH
or --CR; if P is --N.sup.+R.sub.5(X.sup.-).sub.r- , then K.dbd.M
and is --CH or --CR; if Z is --NR.sub.2 and 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.3 or R.sub.4 of structure A.sub.2 is other than a
C.sub.1-C.sub.4 alkyl radical; the symbol B represents: (a) a group
of structure B.sub.1 below: 21in which structure B.sub.1, R.sub.8
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 radical --OH, a radical
--NO.sub.2, --NHR.sub.11 radicals, --NR.sub.12R.sub.13 radicals,
and --NHCO(C.sub.1-C.sub.4)alkyl radicals or forms, with R.sub.9, a
5- or 6-membered ring which may contain at least one hetero atom
chosen from nitrogen, oxygen and sulphur; R.sub.9 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.10 or R.sub.11, a 5- or
6-membered ring which may contain at least one hetero atom chosen
from nitrogen, oxygen and sulphur; R.sub.10 is chosen from a
hydrogen atom, an --OH radical, --NHR.sub.11, radicals and
--NR.sub.12R.sub.13 radicals; R.sub.11 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.12 and R.sub.13, 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; or (b) a 5- or
6-membered nitrogenous heterocyclic group which can contain at
least one other hetero atom and/or at least one carbonyl group and
which can have at least one substituent chosen from C.sub.1-C.sub.4
alkyl, amino and phenyl radicals, and (ii) at least one compound
chosen from glycerol, polyols containing at least 4 carbon atoms,
C.sub.1-C.sub.8 aliphatic ethers of C.sub.3-C.sub.9 polyols, and
C.sub.6-C.sub.8 aromatic ethers of C.sub.2-C.sub.9 polyols, and a
second compartment contains a composition comprising at least one
oxidizing agent.
Description
[0001] The invention relates to a dye composition for keratin
fibers, in particular for human keratin fibers such as the hair,
comprising, in a medium which is suitable for dyeing, at least one
cationic direct dye of given formula, and at least glycerol and/or
one specific polyol and/or polyol ether.
[0002] The invention also relates to the dyeing processes and
devices using the composition.
[0003] Two types of coloration can be distinguished in the field of
hair treatment.
[0004] The first is semi-permanent or temporary dyeing, or direct
dyeing, which involves dyes capable of giving the hair's natural
color a more or less pronounced color change which may withstand
shampooing several times. These dyes are known as direct dyes; they
can be used with or without an oxidizing agent. In the presence of
an oxidizing agent, the aim is to obtain a lightening coloration.
The lightening coloration is carried out by applying to the hair
the mixture, prepared at the time of use, of a direct dye and an
oxidizing agent, and in particular makes it possible to obtain, by
lightening the melanin in the hair, an advantageous effect such as
a unified color in the case of grey hair, or to bring out the color
in the case of naturally pigmented hair.
[0005] The second is permanent dyeing or oxidation dyeing. This is
carried out with dyes known as "oxidation" dyes comprising
oxidation dye precursors and couplers. Oxidation dye precursors,
commonly known as "oxidation bases", are initially colorless or
weakly colored compounds which develop their dyeing power on the
hair in the presence of oxidizing agents added at the time of use,
leading to the formation of colored compounds and dyes. The
formation of these colored compounds and dyes results either from
an oxidative condensation of the "oxidation bases" with themselves
or from an oxidative condensation of the "oxidation bases" with
coloration modifier compounds commonly known as "couplers", which
are generally present in the dye compositions used in oxidation
dyeing.
[0006] In order to vary the shades obtained with the said oxidation
dyes, or to enrich them with glints, it is known to add direct dyes
thereto.
[0007] Among the cationic direct dyes available in the field of
dyeing keratin fibers, in particular human keratin fibers,
compounds which are already known are those whose structure is
developed in the text which follows; nevertheless, these dyes lead
to colorations which have properties that are still insufficient,
e.g., the homogeneity of the color distributed along the fiber
("unison"), in which case it is said that the coloration is too
selective, the staying power, in terms of resistance to the various
attacking factors to which the hair may be subjected (light, bad
weather, shampooing) and the intensity.
[0008] After considerable research conducted in this matter, the
inventors have now discovered that it is possible to obtain novel
compositions for dyeing keratin fibers, which are capable of
leading to colorations which can be more resistant to the various
attacking factors to which the hair may be subjected, and can be
more intense and less selective, by combining at least glycerol
and/or one specific polyol andlor polyol ether with at least one
cationic direct dye known in the prior art, and of formula (I)
defined below.
[0009] This discovery forms the basis of the present invention.
[0010] A first subject of the present invention is thus a
composition for dyeing keratin fibers, and in particular human
keratin fibers such as the hair, containing, in a medium which is
suitable for dyeing, (i) at least one cationic direct dye whose
structure corresponds to formula (I) below, characterized in that
it also contains (ii) at least glycerol and/or one specific polyol
and/or polyol ether.
[0011] (i) The cationic direct dye which can be used according to
the present invention is a compound of formula (I) below:
A--B.dbd.N--B (I)
[0012] in which:
[0013] the symbol A represents a group chosen from structures
A.sub.1 to A.sub.3 below: 1
[0014] in which structures A.sub.1 to A.sub.3,
[0015] R, is chosen from C.sub.1-C.sub.4 alkyl radicals and a
phenyl radical having a substituent chosen from C.sub.1-C.sub.4
alkyl radicals and halogen atoms chosen from chlorine, bromine,
iodine and fluorine;
[0016] R.sub.2 is chosen from C.sub.1-C.sub.4 alkyl radicals and a
phenyl radical;
[0017] 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, in the case of structure A.sub.1, can together form a
substituted benzene ring, and in the case of structure A.sub.2, can
together form a benzene ring optionally having at least one
substituent chosen from C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4
alkoxy and NO.sub.2 radicals;
[0018] R.sub.3 can ailso denote a hydrogen atom;
[0019] Z is chosen from an oxygen atom, a sulphur atom, and
--NR.sub.2 groups;
[0020] M is chosen from --CH, --CR, where R is chosen from
C.sub.1-C.sub.4 alkyl radicals, and --N.sup.+R.sub.5(X.sup.-).sub.r
groups;
[0021] K is chosen from --CH, --CR, where R is chosen from
C.sub.1-C.sub.4 alkyl radicals, and --N.sup.+R.sub.5(X.sup.-).sub.r
groups;
[0022] P is chosen from --CH, --CR, where R is chosen from
C.sub.1-C.sub.4 alkyl radicals, and --N.sup.+R.sub.5(X.sup.-).sub.r
groups;
[0023] r denotes 0 or 1;
[0024] R.sub.5 is chosen from an atom O.sup.-, C.sub.1-C.sub.4
alkoxy radicals and C.sub.1-C.sub.4 alkyl radicals;
[0025] R.sub.6 and R.sub.7, 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 an --NO.sub.2
radical;
[0026] X.sup.- is an anion, preferably chosen from chloride,
iodide, methyl sulphate, ethyl sulphate, acetate and
perchlorate;
[0027] with the proviso that,
[0028] if R.sub.4 is a C.sub.1-C.sub.4 alkyl radical and Z is a
sulphur atom, R.sub.3 is not a hydrogen atom;
[0029] if R.sub.5 is O.sup.-, then r is zero;
[0030] if K or P or M is --N.sup.+--C.sub.1-C.sub.4 -alkyl X.sup.-,
then R.sub.6 or R.sub.7 is other than a hydrogen atom;
[0031] if K is -N.sup.+R.sub.5(X.sup.-).sub.r, then M.dbd.P and is
--CH or --CR;
[0032] if M is --N.sup.+R.sub.5(X.sup.-).sub.r, then K.dbd.P and is
--CH or --CR;
[0033] if P is --N.sup.+R.sub.5(X.sup.-).sub.r, then K.dbd.M and is
--CH or --CR;
[0034] if Z is --NR.sub.2 and 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.3 or
R.sub.4 of structure A.sub.2 is other than a C.sub.1-C.sub.4 alkyl
radical;
[0035] the symbol B represents:
[0036] (a) a group of structure B.sub.1 below: 2
[0037] in which structure B.sub.1,
[0038] R.sub.8 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 radical --OH, a
radical --NO.sub.2, --NHR.sub.11 radicals, --NR.sub.12R.sub.13
radicals, and --NHCO(C.sub.1-C.sub.4)alkyl radicals or forms, with
R.sub.9, a 5- or 6-membered ring which may contain at least one
hetero atom chosen from nitrogen, oxygen and sulphur;
[0039] R.sub.9 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.10 or R.sub.11, a 5- or 6-membered ring which may contain at
least one hetero atom chosen from nitrogen, oxygen and sulphur;
[0040] R.sub.10 is chosen from a hydrogen atom, an --OH radical,
--NHR.sub.11 radicals and --NR.sub.12R.sub.13 radicals;
[0041] R.sub.11 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;
[0042] R.sub.12 and R.sub.13, 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; or
[0043] (b) a 5- or 6-membered nitrogenous heterocyclic group which
can contain at least one other hetero atom and/or at least one
carbonyl group and which can have at least one substituent chosen
from C.sub.1-C.sub.4 alkyl, amino and phenyl radicals, and in
particular a group of structure B2 below: 3
[0044] in which structure B2, R.sub.14 and R.sub.15, which may be
identical or different, are chosen from a hydrogen atom and
C.sub.1-C.sub.4 alkyl and phenyl radicals;
[0045] Y denotes a --CO-- radical or a radical 4
[0046] n=0 or 1, where, when n denotes 1, U denotes a --CO--
radical.
[0047] In the structures defined above, the C.sub.1-C.sub.4 alkyl
or alkoxy group preferably denotes methyl, ethyl, butyl, methoxy or
ethoxy.
[0048] The cationic direct dyes of formula (I) which can be used in
the dye compositions in accordance with the invention are known
compounds and are described, for example, in patent applications
FR-2,189,006, FR-2,285,851 and FR-2,140,205 and its Certificates of
Addition, the disclosures of all of which are specifically
incorporated by reference herein.
[0049] Among the cationic direct dyes of formula (I) which can be
used in the dye compositions in accordance with the invention,
those of formula (I) in which the symbol A denotes structure A3
while the symbol B denotes structure B1 or B2 are particularly
preferred.
[0050] Among these compounds, mention may especially be made more
particularly of the compounds of structures (I).sub.1 to
(II).sub.77 below: 5
[0051] The cationic direct dye(s) used according to the invention
preferably represent(s) from 0.001 to 10% by weight approximately
relative to the total weight of the dye composition, and even more
preferably from 0.005 to 5% by weight approximately relative to
this weight.
[0052] (ii) For the purposes of the invention, the term "polyol"
denotes a compound of linear, branched or cyclic, saturated or
unsaturated alkyl type bearing at least two --OH functions on the
alkyl chain, as well as the polymers (polyethers) of these
polyhydroxyalkyl compounds.
[0053] The specific polyols used according to the invention contain
at least 4 carbon atoms and can be chosen in particular from
C.sub.4-C.sub.9 polyols and polyalkylene glycols such as, more
particularly, polyethylene glycols and polypropylene glycols.
[0054] Among the C.sub.4-C.sub.9 polyols, mention may be made in
particular of 2-butene-1,4-diol, pentane-1,5-diol,
2,2-dimethylpropane-1,3-diol, 3-methylpentane-1,5-diol,
pentane-1,2-diol, 2,2,4-trimethylpentane-1,3-diol,
2-methylpropane-1,3-diol, hexylene glycol, 1,3-butylene glycol,
dipropylene glycol, diethylene glycol and triethylene glycol.
[0055] The specific polyol ethers according to the invention are
chosen from C.sub.1-C.sub.8 aliphatic ethers of C.sub.3-C.sub.9
polyols and C.sub.6-C.sub.8 aromatic ethers of C.sub.2-C.sub.9
polyols.
[0056] Among the C.sub.1-C.sub.8 aliphatic ethers of
C.sub.3-C.sub.9 polyols, mention may be made in particular of
propylene glycol monomethyl ether, propylene glycol monoethyl
ether, isopropylene glycol dimethyl ether, diethylene glycol
monomethyl ether and monoethyl ether, dipropylene glycol monomethyl
ether, tripropylene glycol monomethyl ether and diethylene glycol
dimethyl ether;
[0057] among the C.sub.6-C.sub.8 aromatic ethers of C.sub.2-C.sub.9
polyols, mention may be made in particular of ethylene glycol
monophenyl ether, ethylene glycol monobenzyl ether, propylene
glycol monophenyl ether, propylene glycol monobenzyl ether,
diethylene glycol monophenyl ether and diethylene glycol monobenzyl
ether.
[0058] The glycerol and/or the polyol(s) and/or polyol ether(s)
described for the purposes of the invention are present in the dye
composition in accordance with the invention in proportions
generally ranging from 0.1 to 40% by weight, and even more
particularly from 0.5 to 20% by weight, relative to the total
weight of the composition.
[0059] The medium which is suitable for dyeing (or support)
generally comprises a mixture of water and at least glycerol and/or
a polyol and/or polyol ether as defined above. It can also contain
one or more organic solvents other than glycerol and/or the
polyol(s) and/or polyol ether(s) used in accordance with the
invention, to dissolve the compounds which would not be
sufficiently soluble in water. Organic solvents which may be
mentioned, for example, are C.sub.1-C.sub.4 alkanols such as
ethanol and isopropanol, as well as aromatic alcohols such as
benzyl alcohol, similar products and mixtures thereof.
[0060] The said additional organic solvents can be present in
proportions preferably approximately ranging from 0.5 to 40% by
weight relative to the total weight of the dye composition, and
even more preferably approximately from 1 to 20% by weight.
[0061] The pH of the dye composition in accordance with the
invention generally approximately ranges from 2 to 11, and
preferably approximately from 5 to 10 . It can be adjusted to the
desired value using acidifying or basifying agents usually used for
dyeing keratin fibers.
[0062] Among the acidifying agents which may be mentioned, for
example, are inorganic or organic acids such as hydrochloric acid,
orthophosphoric acid, sulphuric acid, carboxylic acids such as
acetic acid, tartaric acid, citric acid or lactic acid, and
sulphonic acids.
[0063] Among the basifying agents which may be mentioned, for
example, are aqueous ammonia, alkaline carbonates, alkanolamines
such as mono-, di- and triethanolamine and derivatives thereof,
sodium hydroxide, potassium hydroxide and the compounds of formula
(II) below: 6
[0064] in which W is a propylene residue optionally having a
substituent chosen from a hydroxyl group and C.sub.1-C.sub.6 alkyl
radicals; R.sub.16, R.sub.17, R.sub.18 and R.sub.19, which may be
identical or different, are chosen from a hydrogen atom and
C.sub.1-C.sub.6 alkyl and C.sub.1-C.sub.6 hydroxyalkyl
radicals.
[0065] In addition to the cationic direct dye(s) defined above, the
dye composition in accordance with the invention can contain one or
more additional direct dyes which may be chosen, for example, from
nitrobenzene dyes, anthraquinone dyes, naphthoquinone dyes,
triarylmethane dyes, xanthene dyes and azo dyes which are
non-cationic.
[0066] When it is intended for oxidation dyeing, in addition to the
cationic direct dye(s) and glycerol and/or specific polyol and/or
polyol ether defined above, the dye composition in accordance with
the invention contains one or more oxidation bases chosen from the
oxidation bases conventionally used for oxidation dyeing and among
which mention may be made in particular of para-phenylenediamines,
bis(phenyl)alkylenediamines- , para-aminophenols,
ortho-aminophenols and heterocyclic bases.
[0067] When it is (they are) used, the oxidation base(s) preferably
represent(s) from 0.0005 to 12% by weight approximately relative to
the total weight of the dye composition, and even more preferably
from 0.005 to 6% by weight approximately relative to this
weight.
[0068] When it is intended for oxidation dyeing, in addition to the
cationic direct dye and glycerol and/or specific polyol and/or
polyol ether defined above as well as oxidation bases, the dye
composition in accordance with the invention can also contain one
or more couplers so as to modify or enrich with glints the shades
obtained using the cationic direct dye(s) and the oxidation
bases.
[0069] The couplers which can be used in the dye composition in
accordance with the invention can be chosen from the couplers used
conventionally in oxidation dyeing and among which mention may be
made in particular of meta-phenylenediamines, meta-aminophenols,
meta-diphenols and heterocyclic couplers.
[0070] When it is (they are) present, the coupler(s) preferably
represent(s) from 0.0001 to 10% by weight approximately relative to
the total weight of the dye composition, and even more preferably
from 0.005 to 5% by weight approximately relative to this
weight.
[0071] The dye composition in accordance with the invention can
also contain various adjuvants conventionally used in compositions
for dyeing the hair, such as antioxidants, penetrating agents,
sequestering agents, fragrances, buffers, dispersing agents,
surfactants, film-forming agents, ceramides, preserving agents,
screening agents and opacifiers.
[0072] Needless to say, a person skilled in the art will take care
to select this or these optional complementary compound(s) such
that the advantageous properties intrinsically associated with the
dye composition in accordance with the invention are not, or are
not substantially, adversely affected by the addition(s)
envisaged.
[0073] The dye composition according to the invention can be in
various forms, such as in the form of liquids, shampoos, creams or
gels or any other form which is suitable for dyeing keratin fibers,
and in particular human hair. It can be obtained by mixing, at the
time of use, a composition, which may be in pulverulent form,
containing the cationic direct dye(s) with a composition containing
the glycerol and/or the specific polyol and/or polyol ether.
[0074] When the combination of the cationic direct dye and glycerol
and/or specific polyol and/or polyol ether defined according to the
invention is used in a composition intended for oxidation dyeing
(one or more oxidation bases are then used, optionally in the
presence of one or more couplers), or when it is used in a
composition intended for lightening direct dyeing, then the dye
composition in accordance with the invention also contains at least
one oxidizing agent chosen, for example, from hydrogen peroxide,
urea peroxide, alkali metal bromates, persalts such as perborates
and persulphates, and enzymes such as peroxidases, laccases and
two-electron oxidoreductases. The use of hydrogen peroxide or
enzymes is particularly preferred.
[0075] Another subject of the invention is a process for dyeing
keratin fibers, and in particular human keratin fibers such as the
hair, using the dye composition as defined above.
[0076] According to a first variant of this dyeing process in
accordance with the invention, at least one dye composition as
defined above is applied to the fibers, for a period which is
sufficient to develop the desired coloration, after which the
fibers are rinsed, optionally washed with shampoo, rinsed again and
dried.
[0077] The time required to develop the coloration on the keratin
fibers generally ranges from 3 to 60 minutes and even more
preferably from 5 to 40 minutes.
[0078] According to a second variant of this dyeing process in
accordance with the invention, at least one dye composition as
defined above is applied to the fibers, for a period which is
sufficient to develop the desired coloration, without final
rinsing.
[0079] According to one specific embodiment of this dyeing process,
and when the dye composition in accordance with the invention
contains at least one oxidation base and at least one oxidizing
agent, the dyeing process includes a preliminary step which
comprises separately storing, on the one hand, a composition (A1)
comprising, in a medium which is suitable for dyeing, at least one
cationic direct dye and at least glycerol and/or one specific
polyol and/or polyol ether as defined above and at least one
oxidation base, and, on the other hand, a composition (B1)
containing, in a medium which is suitable for dyeing, at least one
oxidizing agent, and then in mixing them together at the time of
use, after which this mixture is applied to the keratin fibers.
[0080] According to another specific embodiment of this dyeing
process, and when the dye composition in accordance with the
invention contains at least one oxidizing agent, the dyeing process
includes a preliminary step which comprises separately storing, on
the one hand, a composition (A2) comprising, in a medium which is
suitable for dyeing, at least one cationic direct dye and at least
glycerol and/or one specific polyol and/or polyol ether as defined
above, and, on the other hand, a composition (B1) containing, in a
medium which is suitable for dyeing, at least one oxidizing agent,
and then in mixing them together at the time of use, after which
this mixture is applied to the keratin fibers.
[0081] Another subject of the invention is a multi-compartment
dyeing device or "kit" or any other multi-compartment packaging
system, a first compartment of which comprises composition (A1) or
(A2) as defined above and a second compartment of which comprises
composition (B1) 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, assigned to the
present assignee.
[0082] The examples which follow are intended to illustrate the
invention without, however, limiting its scope.
EXAMPLES
Example 1
[0083] The dye composition below was prepared:
1 Cationic direct dye of formula (I).sub.27 0.1 g Glycerol 10.0 g
2-Amino-2-methylpropanol qs pH9 Demineralized water qs 100 g A.M.*:
Active material
[0084] The above composition was applied for 30 minutes to locks of
natural grey hair containing 90% white hairs. The locks of hair
were then rinsed, washed with a standard shampoo and then
dried.
[0085] They were dyed in an intense purple shade.
Example 2
[0086] The dye composition below was prepared:
2 Cationic direct dye of formula (I).sub.10 0.12 g Propylene glycol
monomethyl ether 10.0 g 2-Amino-2-methylpropanol qs pH9
Demineralized water qs 100 g A.M.*: Active material
[0087] The above composition was applied for 30 minutes to locks of
natural grey hair containing 90% white hairs. The locks of hair
were then rinsed, washed with a standard shampoo and then
dried.
[0088] They were dyed in an intense red shade.
* * * * *