Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2001-02-23
2003-10-21
Douyon, Lorna M. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S406000, C008S407000, C008S408000, C008S409000, C008S410000, C008S412000
Reexamination Certificate
active
06635091
ABSTRACT:
A subject of the invention is a composition for the oxidation dyeing of keratinous fibers, such as human keratinous fibers such as hair, comprising at least one oxidation base and at least one coupler chosen from N-(2-hydroxybenzene)carbamate and N-(2-hydroxybenzene)urea compounds of formula (I), their use as coupler for the oxidation dyeing of keratinous fibers, and the oxidation dyeing methods using them.
It is known to dye keratinous fibers, for example, human hair with dyeing compositions containing oxidation dye precursors, such as para-phenylenediamines, ortho-, and para-aminophenols, heterocyclic compounds such as diaminopyrazole derivatives, generally called oxidation bases. Oxidation dye precursors, i.e., oxidation bases, are colorless or weakly colored compounds which when combined with oxidizing products, can give rise, through a process of oxidative condensation, to colored or coloring compounds.
It is also known that it is possible to vary the shades obtained with these oxidation bases by combining them with couplers or color modifiers, the latter being chosen, for example, from aromatic meta-diamines, meta-aminophenols, meta-diphenols, noncationic naphthols or alternatively certain heterocyclic compounds such as indolic couplers.
The variety of molecules used in oxidation bases and couplers allows a rich palette of colors to be obtained.
The “permanent” color obtained using these oxidation dyes should moreover satisfy at least one of a number of objectives. Thus, it should, for example, satisfy at least one of the following: be without drawbacks from the toxicological point of view, make it possible to obtain shades in the desired intensity and exhibit good resistance towards external agents (at least one of light, adverse weather conditions, washing, permanent waving, perspiration, and rubbing).
The dyes may also cover grey hair and may also be the least selective possible, that is to say, make it possible to obtain the smallest possible differences in color right along the same keratinous fiber, which may indeed be differently sensitized (i.e. damaged) between its tip and its root.
Oxidation dyeing compositions containing certain derivatives of N-(2-hydroxy-4-aminophenyl)acetamide as couplers have already been described, for example, in patent applications WO 98/52519, JP2521636, FR-A-1 596 879 and FR-A-2 233 984. However, such compositions are not always satisfactory based on the intensity of the colors which may be obtained.
However, the inventors have discovered, completely unexpectedly and surprisingly, that compounds of N-(2-hydroxybenzene)carbamate and N-(2-hydroxybenzene)urea compounds of formula (I) defined below are suitable as couplers for oxidation dyeing, and that they make it possible to obtain dyeing compositions leading to at least one of the following advantages: intense colors which are particularly chromatic and brilliant, colors which are not very selective, a broad palette of colors, and properties of resistance to the various treatments to which keratinous fibers may be subjected.
One embodiment of the invention is therefore a composition for oxidation dyeing keratinous fibers, for example, human keratinous fibers such as hair, comprising in a medium suitable for dyeing:
(a) at least one oxidation base; and
(b) at least one coupler chosen from compounds of formula (I) and acid addition salts thereof:
in which:
R
1
is chosen from a hydrogen atom, linear and branched, saturated and unsaturated (comprising, for example, at least one double bond and at least one triple bond) groups comprising from 1-15 carbon atoms, optionally substituted with at least one halogen atom, wherein at least one carbon atom is optionally replaced by a unit chosen from an oxygen atom, a nitrogen atom, a sulfur atom, and a SO
2
group, and at least one branch of said branched groups optionally forms at least one 3- to 7-membered ring comprising at least one carbon atom, with the provisos that:
(i) said R
1
does not comprise a group chosen from a peroxide group, a diazo group, a nitro group, and a nitroso group, and
(ii) said SO
2
group is not directly linked to the nitrogen at the 7-position of formula (I);
X is chosen from groups OR
5
and NR
6
R
7
, wherein
R
5
is chosen from linear and branched, saturated and unsaturated (comprising, for example, at least one double bond and at least one triple bond) groups comprising from 1-20 carbon atoms, optionally substituted with at least one halogen atom, wherein at least one carbon atom is optionally replaced by a unit chosen from an oxygen atom, a nitrogen atom, a sulfur atom, and a SO
2
group, and at least one branch of said branched groups optionally forms at least one 3- to 7-membered ring comprising at least one carbon atom, with the proviso that:
(i) said R
5
does not comprise a group chosen from a peroxide group, a diazo group, a nitro group, and a nitroso group;
R
6
and R
7
, which are identical or different, are each chosen from a hydrogen atom, linear and branched, saturated and unsaturated (comprising, for example, at least one double bond and at least one triple bond) groups comprising from 1-20 carbon atoms, optionally substituted with at least one halogen atom, wherein at least one carbon atom is optionally replaced by a unit chosen from an oxygen atom, a nitrogen atom, a sulfur atom, and a SO
2
group, and at least one branch of said branched groups optionally forms at least one 3- to 7-membered ring comprising at least one carbon atom, with the proviso that:
(i) both said R
6
and R
7
do not comprise a group chosen from a peroxide group, a diazo group, a nitro group, and a nitroso group, and
said R
6
and R
7
optionally form a ring chosen from a saturated and an unsaturated ring comprising 5- to 7-members, wherein said members are each chosen from a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a carbonyl group, and said members are optionally substituted with 1 or 2 groups R, wherein
R is chosen from linear, branched, saturated and unsaturated (comprising, for example, at least one double bond and at least one triple bond), C
1
-C
6
alkyl groups, optionally substituted with at least one halogen atom, wherein at least one carbon atom is optionally replaced by a unit chosen from an oxygen atom, a nitrogen atom, a sulfur atom, and a SO
2
group, and at least one branch of said branched C
1
-C
6
alkyl group optionally forms at least one saturated or unsaturated 3- to 6-membered ring; with the proviso that:
(i) said R does not comprise a group chosen from a peroxide group, a diazo group, a nitro group, and a nitroso group;
wherein
said R
1
and said R
5
optionally form a ring chosen from a saturated and an unsaturated (comprising, for example, at least one double bond and at least one triple bond) ring comprising 5- to 7-members, wherein said members are each chosen from a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a carbonyl group, and said members are optionally substituted with 1 or 2 groups R as defined above, with the proviso that:
(i) said R does not comprise a group chosen from a peroxide group, a diazo group, a nitro group, and a nitroso group; and
said R
1
and said R
6
optionally form a ring, chosen from a saturated and an unsaturated (comprising, for example, at least one double bond and at least one triple bond) ring comprising 5- to 7-members, wherein said members are each chosen from a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a carbonyl group, and said members are optionally substituted with 1 or 2 groups R as defined above, with the proviso that:
(i) said R does not comprise a group chosen from a peroxide group, a diazo group, a nitro group, and a nitroso group;
R
2
, R
3
, and R
4
, which are identical or different, are each chosen from a hydrogen atom, a halogen atom, and linear and branched, saturated and unsaturated (comprising, for example, at least one double bond and at least one triple bond) groups comprising from 1-20 carbon atoms, optionally substituted with at least one halogen atom, wherein at least one car
Saunier Jean-Baptiste
Vidal Laurent
Douyon Lorna M.
Elhilo Eisa
Finnegan Henderson Farabow Garrett & Dunner
L'Oréal S. A.
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