Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2000-10-03
2003-10-21
Gupta, Yogendra N. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S406000, C008S407000, C008S408000, C008S409000, C546S298000
Reexamination Certificate
active
06635090
ABSTRACT:
The present invention relates to the use, for dyeing keratin fibres, of at least one heterocyclic cationic amine and of at least one compound chosen from a specific aldehyde of formula (III) defined below, a specific ketone of formula (IV) or (V) defined below, a quinone and a diiminoisoindoline or 3-aminoisoindolone derivative, to dye compositions comprising a combination of these compounds, to dyeing processes using the said compounds and to a multi-compartment device containing these compounds.
It is known practice, for the dyeing of keratin fibres, and in particular of human keratin fibres such as the hair, to use direct dyes or coloured substances which give the fibre a temporary or semi-permanent coloration, of low dyeing power, which is generally removed by washing or by perspiration. The range of shades obtained by these direct processes is generally limited. It is also known practice to use oxidation dyes (oxidation bases and couplers), which are compounds which are initially colourless or weakly coloured and which, under the action of an oxidizing agent, generate coloured compounds by a process of oxidative condensation. Compared with direct colorations, oxidative colorations are permanent, powerful and withstand external agents (light, bad weather, washing, perspiration and rubbing). Nevertheless, the use of the oxidizing agent can harm the keratin fibres and make the processes for carrying out the oxidative dyeing operations relatively complex.
The Applicant has just discovered a novel dyeing process, which does not involve a process of oxidative development of dyes, and which gives a wide range of shades.
The compounds used by the Applicant are small molecules which can penetrate into keratin easily. The Applicant has found, surprisingly, that these compounds can then condense to form chromophores or dyes, bulkier molecules which remain trapped inside the keratin.
The Applicant has thus found that the dyes obtained withstand shampooing and perspiration and are stable with respect to light, bad weather and chemical agents. The Applicant has, in a way, discovered a novel dyeing process which has the advantages of so-called oxidation dyeing without exhibiting its drawbacks, since no oxidizing agent is used.
One subject of the present invention is thus the use, for dyeing keratin fibres, of a specific cationic derivative and of a compound chosen from an aldehyde of formula (III), a ketone of formula (IV) or (V), a quinone and a diiminoisoindoline or 3-amino-isoindolone derivative.
Another subject of the invention relates to dye compositions comprising these compounds.
A subject of the present invention is also a process for dyeing keratin fibres, which consists in applying a specific cationic derivative and a compound chosen from an aldehyde of formula (III), a ketone of formula (IV) or (V), a quinone and a diiminoisoindoline or 3-aminoisoindolone derivative to the fibres, either simultaneously, in the form of a mixture prepared at the time of use, or successively.
Another subject of the invention also consists of a dyeing agent for carrying out the process of the invention.
Other subjects of the invention will become apparent in the light of the description.
The main subject of the present invention is thus the use, for dyeing keratin fibres, in particular human keratin fibres such as the hair, of at least one specific cationic derivative and of at least one compound chosen from an aldehyde of formula (III), a ketone of formula (IV) or (V), a quinone and a diiminoisoindoline or 3-aminoisoindolone derivative, in order to obtain, by reaction without an oxidizing agent, a coloration of the said keratin fibres.
In the context of the present invention, the cationic derivatives are chosen from:
the compounds of formula (I) below:
in which:
n denotes an integer from 1 to 4;
R
1
denotes an alkyl, hydroxyalkyl, polyhydroxyalkyl, alkylhydroxyalkyl, alkylsulphonyl, carboxyalkyl, aminoalkyl, (dihydroxy)alkylaminoalkyl, alkyl-NR′R″ (in which R′ and R″ are alkyl or can form, together with the nitrogen atom to which they are attached, a 5- or 6-membered aliphatic or heterocyclic ring) or an aryl radical, the alkyl radicals of the groups defined above containing from 1 to 4 carbon atoms and being linear or branched;
A and the nitrogen together form an unsaturated, aromatic or heterocyclic, 5- or 6-membered hydrocarbon-based ring which may be interrupted with one or more nitrogen, oxygen or sulphur atoms and which may be substituted with one or more radicals such as —NO
2
, —NH
2
, acetylamino, —OH, —SO
3
H, a halogen atom, —CH
3
SO
2
, —CF
3
, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio and (C
1
-C
4
) alkoxycarbonyl,
A denotes a substituted or unsubstituted carbon, a substituted or unsubstituted nitrogen, an oxygen or a sulphur;
the 5- or 6-membered hydrocarbon-based ring formed by A and the nitrogen can also be fused with a substituted or unsubstituted aromatic ring such as, in particular, aryl or naphthyl substituted with one or more halogen, allyl or alkoxy radicals;
or the compounds of formula (II) below:
in which:
R
1
is defined as above,
R
2
, R
3
, R
4
or R
5
, which may be identical or different, denote the substituents denoted by R
1
;
B denotes —CH— or a nitrogen;
the groups R
1
and R
2
, R
2
and R
3
, R
3
and R
4
, R
5
and R
1
, the group R
5
or R
4
and B can form, together with the atoms to which they are attached, an unsaturated, aromatic or heterocyclic, 5- or 6-membered hydrocarbon-based ring which may be interrupted with one or more nitrogen or sulphur atoms and which may be substituted with one or more radicals such as —NO
2
, —NH
2
, acetylamino, —OH, —SO
3
H, a halogen atom, —CH
3
SO
2
, —CF
3
, —OCF
3
, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio and (C
1
-C
4
)alkoxycarbonyl and the cosmetically acceptable salts of these compounds.
The compounds of formula (I) are chosen in particular from the following compounds:
1,2,3-trimethyl-3H-imidazol-1-ium iodide
2,3,4-trimethylthiazol-3-ium iodide
3-ethylmethylbenzothiazolium iodide
3-methylmethylbenzothiazolium methosulphate
1,2,3,3-tetramethyl-3H-indolium iodide
3-ethylmethylbenzoxazolium iodide
1,2,3-trimethyl-3H-imidazol-1-ium methosulphate
3-(2-carboxyethyl)-2,5-dimethylbenzoxazol-3-ium bromide
3-ethylmethylbenzothiazolium toluene-4-sulphonate
5-chloro-3-ethyl-2-methylbenzothiazol-3-ium toluene-4-sulphonate
1-ethyl-2-methylnaphtho[1,2-d]thiazol-1-ium toluene-4-sulphonate
1,2,3-trimethyl-3H-benzoimidazol-1-ium tetrafluoroborate
2-ethyl-3-methylbenzo[d]isothiazol-2-ium tetrafluoroborate
2-methyl-3-(3-sulphonatopropyl)benzothiazol-3-ium
3-tertbutyl-2-methylbenzothiazol-3-ium bromide
3-(2-carboxyethyl)-2,5-dimethylbenzoxazol-3-ium bromide
5-methoxy-2-methyl-3-(3-sulphonatopropyl)benzothiazol-3-ium
2-methyl-1-(3-sulphonatopropyl)naphtho[1,2-d]oxazol-1-ium
2-methyl-3-(3-sulphonatopropyl)naphtho[2,3-d]oxazol-3-ium
2,5,6-trimethyl-3-(3-sulphonatopropyl)thieno[2,3-d]-thiazol-3-ium
1-ethyl-2-methylnaphtho1,2-dioxazol-1-ium perchlorate;
1,2-dimethylnaphtho[1,2-d]thiazol-1-ium methosulphate
3-ethyl-2,5,6-trimethylbenzoxazol-3-ium iodide
2-methyl-1-(3-sulphonatopropyl)naphtho[1,2-d]thiazol-1-ium
1-ethyl-2-methylnaphtho[1,2-d]thiazol-1-ium perchlorate
2-methyl-5-phenyl-3-(3-sulphonatopropyl)benzoxazol-3-ium
3-ethyl-6-methoxy-2-methylbenzothiazol-3-ium iodide
5-methoxy-1,2-dimethylnaphtho[1,2-d]thiazol-1-ium iodide
5-chloro-3-ethyl-2-methylbenzothiazol-3-ium toluene-4-sulphonate
5,6-dimethoxy-2,3-dimethylbenzothiazol-3-ium toluene-4-sulphonate
3-ethyl-2-methylbenzo[4,5]thieno[2,3-d]thiazol-3-ium toluene-4-sulphonate
3-ethyl-2-methylnaphtho[1,2-]thiazol-1-ium toluene-4-sulphonate
5,6-dichloro-3-ethyl-2-methyl-1-(3-sulphonatobutyl) 3H-benzoimidazol-1-ium
2,3-dimethyl-5-phenylbenzoxazol-3-ium methosulphate
5-methoxy-1,2-dimethylbenzo[cd]indolium perchlorate
1-butyl-2,3,3-trimethyl-3H-indolium iodide
1,1,2,3-tetramethyl-1H-benz[e&r
Andrean Herve
Lagrange Alain
Elhilo Eisa
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
Gupta Yogendra N.
L'Oreal (S.A.)
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