Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1999-05-26
2002-03-19
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S407000, C008S426000, C008S654000, C008S655000, C008S657000, C008S659000, C008S406000, C008S408000, C008S410000, C008S411000, C008S412000
Reexamination Certificate
active
06358286
ABSTRACT:
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.
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.
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.
The variety of compounds used as oxidation bases and couplers allows a wide range of colours to be obtained.
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.
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.
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).
The dyes should also be able to cover grey hair and, finally, they should be as unselective as possible, ie., 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.
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.
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:
at least one oxidation base,
at least one cationic direct dye of formula (I) defined below.
This discovery forms the basis of the present invention.
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.
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.
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:
at least one oxidation base,
at least one cationic direct dye of formula (I) below:
A—N═N—B (I)
wherein:
A is chosen from structures A1, A2, and A3 below:
wherein in said structures A1 to A3:
R
1
is chosen from C
1
-C
4
alkyl radicals, a phenyl radical, and phenyl radicals having a substituent chosen from C
1
-C
4
alkyl radicals and halogen atoms chosen from chlorine, bromine, iodine and fluorine;
R
2
is chosen from C
1
-C
4
alkyl radicals and a phenyl radical;
R
3
and R
4
, which may be identical or different, are chosen from C
1
-C
4
alkyl radicals and a phenyl radical or together form a benzene ring having at least one substituent chosen from C
1
-C
4
alkyl radicals, C
1
-C
4
alkoxy radicals, and nitro radicals; R
3
can also be a hydrogen atom;
R
5
and R
6
, which may be identical or different, are chosen from C
1
-C
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
1
-C
4
alkyl radicals, C
1
-C
4
alkoxy radicals, and nitro radicals; R
5
can also be a hydrogen atom;
R
7
and R
8
, which may be identical or different, are chosen from a hydrogen atom, halogen atoms chosen from chlorine, bromine, iodine and fluorine, C
1
-C
4
alkyl radicals, C
1
-C
4
alkoxy radicals and nitro radicals;
Z is chosen from an oxygen atom, a sulphur atom, and a group NR
2
, wherein R
2
is chosen from C
1
-C
4
alkyl radicals and a phenyl radical;
the ring member L is chosen from —CH, —CR and —N
+
R
9
(X
−
)
r
;
the ring member M is chosen from —CH, —CR and —N
+
R
9
(X
−
)
r
;
r is an integer equal to 0 or 1;
R is chosen from C
1
-C
4
alkyl radicals;
R
9
is chosen from an atom O
−
, C
1
-C
4
alkyl radicals, and C
1
-C
4
alkoxy radicals;
X
−
is chosen from an anion preferably chloride, methyl sulphate, ethyl sulphate, acetate, and perchlorate;
with the provisos that:
in the formula A3, at least one of the ring members L and M is chosen from a group —N
+
R
9
(X
−
)
r
;
when R
6
is a C
1
-C
4
alkyl radical and Z is a sulphur atom, then R
5
is other than a C
1
-C
4
alkyl radical;
when R
6
is a C
1
-C
4
alkyl radical and Z is a sulphur atom and when one of the radicals R
10
and R
11
, defined below, is a hydrogen atom, then R
5
is other than a hydrogen atom;
when R
9
is O
−
, then r=0;
when L or M is a radical —N
+
R
9
(X
−
)
r
wherein R
9
is a C
1
-C
4
alkyl radical and r=1, then at least one of the radicals R
7
and R
8
is other than a hydrogen atom;
when L is a radical —N
+
R
9
(X
−
)
r
, then M is chosen from a group —CH and CR;
when M is a radical —N
+
R
9
(X
−
)
r
, then L is chosen from a group —CH and CR;
when Z is a group NR
2
wherein R
2
is a C
1
-C
4
alkyl radical, then at least one of the radicals R
1
, R
5
and R
6
is other than a C
1
-C
4
alkyl radical;
when Z is a sulphur atom and R
1
is a C
1
-C
4
alkyl radical and when one of the radicals R
10
and R
11
, defined below, is a hydrogen atom, then R
5
and R
6
cannot together form an unsubstituted benzene ring;
B is chosen from:
(a) a group of structure B1 below:
wherein in structure B1,
R
10
is chosen from a hydrogen atom, halogen atoms chosen from chlorine, bromine, iodine and fluorine, C
1
-C
4
alkyl radicals, C
1
-C
4
alkoxy radicals, a hydroxyl radical, —NHR
13
groups, —NR
14
R
15
groups, —NHCO(C
1
-C
4
)alkyl groups and a nitro, or forms with R
11
a 5- or 6-membered carbon ring or a ring containing at least one hetero atom chosen from nitrogen, oxygen and sulphur;
R
11
is chosen from a hydrogen atom, halogen atoms chosen from chlorine, bromine, iodine and fluorine, C
1
-C
4
alkyl radicals, and C
1
-C
4
alkoxy radicals or forms with R
12
or R
13
a 5- or 6-membered carbon ring or a ring containing at least one hetero atom chosen from nitrogen, oxygen and sulphur;
R
12
is chosen from a hydrogen atom, a hydroxyl radical, —NHR
13
radicals, and —NR
14
R
15
radicals;
R
13
is chosen from a hydrogen atom, C
1
-C
4
alkyl radicals, C
1
-C
4
monohydroxyalkyl radicals, C
2
-C
4
polyhydroxyalkyl radicals, and a phenyl radical;
R
14
and R
15
, which may be identical or different, are chosen from C
2
-C
4
alkyl radicals, C
1
-C
4
monohydroxyalkyl radicals, and C
2
-C
4
polyhydroxyalkyl radicals; and
(b) a 5- or 6-membered nitrogenous heterocyclic group, a 5- or 6-membered
Cotteret Jean
Lang Gerard
Einsmann Margaret
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
L'Oreal (S.A.)
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