Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2000-10-27
2002-09-17
Gupta, Yogendra N. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S406000, C008S409000, C008S410000, C008S535000, C008S607000, C008S608000, C008S657000, C008S426000
Reexamination Certificate
active
06451067
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 an aldehyde, a ketone, 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. The ranges of shades obtained by these direct processes are generally limited. It is also known practice to use oxidation dyes (oxidation basis 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 makes 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 given a wide range of shades.
The compounds used by the Applicant are small molecules which can penetrate into keratin easily. The Applicant has found, suprisingly, that those 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. These colorations withstand shampooing particularly well. 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 oxidizing agent is used.
One subject of the present invention is thus the use, for dyeing keratin fibres, of a heterocyclic cationic amine and of a compound chosen from an aldehyde, a ketone, a quinone and a diiminoisoindoline or 3-aminoisoindolone 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 heterocyclic cationic amine and a compound chosen from an aldehyde, a ketone, 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 and the examples which follow.
The main subject of the present invention is thus the use, for dyeing keratin fibres, in particular human keratin fibres such as human hair, of at least one heterocyclic cationic amine and of at least one compound chosen from an aldehyde, a ketone, 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.
For the purposes of the invention, the exxpression “heterocyclic cationic amine” means a molecule comprising at least one amine function, at least one heterocycle, preferably a nitrogenous heterocycle, and at least one positve group, preferably on the heterocycle.
The heterocyclic cationic amine is chosen from the compounds of formula (I) below and the cosmetically acceptable salts thereof:
in which:
R
1
, R
2
, R
3
and R
4
, which may be identical or different, represent a hydrogen atom; a halogen atom, an -NH
2
group, an -OH group Z; a group Z; a group -COZ; a group -COOZ; an alkylcarbonyl radical; an aminoalkylcarbonyl radical; an N-alkylaminoalkylcarbonyl radical; an N,N-dialkylaminoalkylcarbonyl radical; an aminoalkylcarbonylalkyl radical; an N-alkylaminoalkycarbonylalkyl radical; an N,N-dialkylaminoalkylcarbonylalkyl radical; a carboxyl radical; an alkylcarboxyl radical; an alkylsulphonyl radical; an aminosulphonyl radical; an N-alkylaminosulphonyl radical; an N,N-dialkylaminosulphonyl radical; an aminosulphonylalkyl radical; an N-alkylaminosulphonylalkyl radical; an N,N-dialkylaminosulphonylalkyl radical; a carbamyl radical; an N-alkylcarbamyl radical; an N,N-dialkylcarbamyl radical; a carbamylalkyl radical; an N-alkylcarbamylalkyl radical; an N,N-dialkylcarbamylalkyl radical; an alkyl, monohydroxyalkyl, polyhydroxyalkyl, alkoxyalkyl or trifluoroalkyl radical or a cyano radical; a group OR
1
, SR
1
, OR
1
Z or SR
1
Z or an amino group protected with an alkylcarboxyl, trifluoroalkylcarbonyl, aminoalkylcarbonyl, carbonyl, N-alklaminoalkylcarbonyl, N,N-dialkylaminoalkylcarbonyl, alkylcarboxyl, carbamyl, N-alkylcarbamyl, N,N-dialkylcarbamyl, alkylsulphonyl, aminosulphonyl, N-alkylaminosulphonyl, N,N-dialkylaminosulphonyl, thiocarbamyl or formyl radical, a group -COZ or a group -COOZ;
R
1
denotes an alkyl, monohydroxyalkyl or polyhydroxyalkyl radical, a group Z, an alkoxyalkyl radical; an aryl radical; a benzyl radical, a carboxyalkyl radical, an alkoxycarboxyalkyl radical, a cyanoalkyl radical, a carbamylalkyl radical or an N-alkylcarbamylalkyl radical; an N,N-dialkylcarbamylalkyl radical; a trifluoroalkyl radical; an aminosulphonylalkyl radical; an N-alkylaminosulphonylalkyl radical; an N,N-dialkylaminosulphonylalkyl radical; an alkylsulphinylalkyl radical; an alkylsulphonylaklyl radical; an alkylcarbonylalkyl radical; an aminoalkyl radical; an aminoalkyl radical in which the amine is substituted with one or two radicals, which may be identical or different, chosen from alkyl, monohydroxyalkyl, polyhydroxyalkyl, alkylcarbonyl, formyl, trifluoroalkylcarbonyl, alkylcarboxyl, carbamyl, N-alkylcarbamyl, N,N-dialkylcarbamyl, thiocarbamyl and alkylsulphonyl radicals and from the groups Z, -COZ or -COOZ;
Z representing a group of formula (II) or (III) below:
in which:
D is a linker arm which represents a linear or branched alkyl chain preferably containing from 1 to 14 carbon atoms, which can be interrupted by one or more hetero atoms such as oxygen, sulphur or nitrogen atoms, and which can be substituted with one or more hydroxyl or C
1
-C
6
alkoxy radicals, and which can bear one or more ketone functions;
the ring members E, G, J, L and M, which may be identical or different, represent a carbon, oxygen, sulphur or nitrogen atom;
n is an integer between 0 and 4 inclusive;
m is an integer between 0 and 5 inclusive;
the radicals R
5
, which may be identical or different, represent one of the two valencies of a linker arm D, a second group Z which is identical to or different from the first group Z, a halogen atom, a hydroxyl radical, a C
1
-C
6
alkyl radical, a C
1
-C
6
monohydroxyalkyl radical, a C
2
-C
6
polyhydroxyalkyl radical, a nitro radical, a cyano radical, a cyano(C
1
-C
6
)alkyl radical, a C
1
-C
6
alkoxy radical, a tri(C
1
-C
6
)alkylsilane(C
1
-C
6
)alkyl radical, an amido radical, an aldehydo radical, a carboxyl radical, a (C
1
-C
6
)alkylcarbonyl radical, a thio radical, a C
1
-C
6
thioalkyl radical, a C
1
-C
6
alkylthio radical, an amino radical, an amino radical protected with a (C
1
-C
6
)alkylcarbonyl, carbamyl or C
1
-C
6
alkyl sulphonyl radical; a group NHR″ or NR″RO in which R″ and RO, which may be identical or different, represent a C
1
-C
6
alkyl radical, a C
1
-C
6
monohydroxyalkyl radical or a C
2
-C
6
polyhydroxylalkyl radical;
R
6
represents one of the two valencies of a linker arm B, a C
1
-C
4
alkyl radical, a C
1
-C
6
monohydroxyalkyl radical, a C
2
-C
6
polyhydroxyalkyl radical, a cyano-(C
1
-C
6
)alkyl radical, a tri(C
1
-C
6
)alkylsi
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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