Cationic 4-hydroxyindoles, their use for the oxidation...

Details Cationic 4-hydroxyindoles, their use for the oxidation... Cationic 4-hydroxyindoles, their use for the oxidation...

2001-08-09

2003-03-04

Davis, Zinna Northington (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S275100, C546S277400, C548S312100, C548S490000, C548S504000

Reexamination Certificate

active

06528650

ABSTRACT:

The invention relates to novel 4-hydroxyindole derivatives comprising at least one cationic group Z, Z being selected from quaternized aliphatic chains, aliphatic chains containing at least one quaternized saturated ring, and aliphatic chains containing at least one quaternized unsaturated ring, to their use as a coupler for the oxidation dyeing of keratinous fibers, to the dyeing compositions comprising them, and to the methods of oxidation dyeing which employ them.
It is known to dye keratinous fibers, and especially human hair, with dyeing compositions comprising oxidation dye precursors, especially para-phenylenediamines, ortho- or para-aminophenols, and heterocyclic compounds, such as diaminopyrazole derivatives, which are referred to generally as oxidation bases. The oxidation dye precursors or oxidation bases are colourless or slightly coloured compounds which, when combined with oxidizing products, have the capacity to give rise to coloured compounds and dyes by virtue of 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 coloration modifiers, the latter being selected in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as, for example, indole couplers.
The variety of molecules employed as oxidation bases and couplers makes it possible to obtain a wide range of colours.
The so-called permanent coloration obtained by virtue of these oxidation dyes should, moreover, satisfy certain conditions. Hence it should have no toxicological drawbacks, should allow shades of the desired intensity to be obtained, and should have good resistance to external agents (light, inclement weather, washing, permanent-waving, perspiration and friction).
The dyes should also allow white hair to be covered and, finally, they should be as unselective as possible; in other words, they should allow the smallest possible differences in coloration to be produced over the entire length of a single keratinous fibre, which may in fact be sensitized (i.e. damaged) differently between its tip and its root.
The inventors have now discovered, in a manner totally unexpected and surprising, that a novel class of 4-hydroxyindole derivatives of formula (I) defined below, containing at least one cationic group Z, Z being selected from quaternized aliphatic chains, aliphatic chains containing at least one quaternized saturated ring, and aliphatic chains containing at least one quaternized unsaturated ring, are suitable for use as a coupler for oxidation dyeing and that, furthermore, they make it possible to obtain dyeing compositions which lead to intense colorations in a very wide range of shades and have excellent properties of resistance to the various treatments which the keratinous fibers may undergo. Finally, these compounds have been found to be readily synthesizable.
It is these discoveries which form the basis of the present invention.
The invention therefore provides, firstly, 4-hydroxyindole derivatives of formula (I) below and their addition salts with an acid:
in which:
R
1
represents a hydrogen atom; a group Z; a C
1
-C
4
alkyl radical; a C
1
-C
4
monohydroxyalkyl radical; a C
2
-C
4
polyhydroxyalkyl radical; a (C
1
-C
4
alkoxy)-C
1
-C
4
alkyl radical; a hydroxy(C
1
-C
4
alkoxy)-C
1
-C
4
alkyl radical; a C
1
-C
4
aminoalkyl radical; a C
1
-C
4
aminoalkyl radical whose amine is mono- or disubstituted by a C
1
-C
4
alkyl radical, by an acetyl radical, by a C
1
-C
4
monohydroxyalkyl radical or by a C
2
-C
4
polyhydroxyalkyl radical; a (C
1
-C
4
alkyl)-C
1
-C
4
thioalkyl radical, a monohydroxy(C
1
-C
4
alkyl)-C
1
-C
4
thioalkyl radical; a polyhydroxy(C
2
-C
4
alkyl)-C
1
-C
4
alkyl radical; a C
1
-C
4
carboxyalkyl radical; a (C
1
-C
4
alkoxy)-C
1
-C
4
thiocarbonylalkyl radical or a C
1
-C
4
acetylaminoalkyl radical; a C
1
-C
4
cyanoalkyl radical; a C
1
-C
4
trifluoroalkyl radical; a C
1
-C
4
haloalkyl radical; a C
1
-C
4
phosphoalkyl radical, or a C
1
-C
4
sulphoalkyl radical;
R
2
and R
3
, which are identical or different, represent a hydrogen or halogen atom; a group Z; a group —NH—Z; a C
1
-C
4
alkyl radical; a carboxyl radical; a (C
1
-C
4
alkoxy)carbonyl radical or a formyl radical;
R
4
and R
5
, which are identical or different, represent a hydrogen or halogen atom; a group Z; a group —NH—Z; a C
1
-C
4
alkyl radical; a C
1
-C
4
alkoxy radical; an acetylamino radical; a C
1
-C
5
monohydroxyalkyl radical; a C
2
-C
4
polyhydroxyalkyl radical; a (C
1
-C
4
alkoxy)-C
1
-C
4
alkyl radical; a thiophene radical; a furan radical; a phenyl radical; an aralkyl radical in which the alkyl moiety is C
1
-C
4
; a phenyl radical or aralkyl radical in which the alkyl moiety is C
1
-C
4
, each substituted by a halogen atom, by a C
1
-C
4
alkyl radical, by a trifluoromethyl radical, by a C
1
-C
4
alkoxy radical, by an amino radical or by an amino radical which is mono- or disubstituted by a C
1
-C
4
alkyl radical; a (C
1
-C
4
alkyl)-C
1
-C
4
aminoalkyl radical or a di(C
1
-C
4
alkyl)-C
1
-C
4
aminoalkyl radical;
Z is selected from the unsaturated cationic groups of formulae (II) and (III) below and the saturated cationic groups of formula (IV) below:
in which:
D is a linker which represents an alkyl chain containing preferably 1 to 14 carbon atoms, which is linear or branched and can be interrupted by one or more heteroatoms such as oxygen, sulphur or nitrogen atoms and can be substituted by one or more hydroxyl or C
1
-C
6
alkoxy radicals and can carry one or more ketone functional groups;
the ring members E, G, J, L and M, which are identical or different, represent a carbon, oxygen, sulphur or nitrogen atom;
n is an integer of between 0 and 4 inclusive;
m is an integer of between 0 and 5 inclusive;
the radicals R, which are identical or different, represent a 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 C
1
-C
6
cyanoalkyl radical, a C
1
-C
6
alkoxy radical, a tri(C
1
-C
6
alkyl)silyl-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
alkyl)thio radical, an amino radical, an amino radical protected by a (C
1
-C
6
alkyl)carbonyl, carbamyl or (C
1
-C
6
alkyl)sulphonyl radical; a group NHR″ or NR″R′″ in which R″ and R′″, which are identical or different, represent a C
1
-C
6
alkyl radical, a C
1
-C
6
monohydroxyalkyl radical or a C
2
-C
6
polyhydroxyalkyl radical;
R
6
represents a C
1
-C
6
alkyl radical, a C
1
-C
6
monohydroxyalkyl radical, a C
2
-C
6
polyhydroxyalkyl radical, a C
1
-C
6
cyanoalkyl radical, a tri(C
1
-C
6
alkyl)silyl-C
1
-C
6
alkyl radical, a (C
1
-C
6
alkoxy)-C
1
-C
6
alkyl radical, a C
1
-C
6
carbamylalkyl radical, a (C
1
-C
6
alkyl)-C
1
-C
6
carboxyalkyl radical, a benzyl radical or a group Z of formula (II), (III) or (IV) as defined above;
R
7
, R
8
and R
9
, which are identical or different, represent a C
1
-C
6
alkyl radical, a C
1
-C
6
monohydroxyalkyl radical, a C
2
-C
6
polyhydroxyalkyl radical, a (C
1
-C
6
alkoxy)-C
1
-C
6
alkyl radical, a C
1
-C
6
cyanoalkyl radical, an aryl radical, a benzyl radical, a C
1
-C
6
amidoalkyl radical, a tri(C
1
-C
6
alkyl)silyl-C
1
-C
6
alkyl radical or a C
1
-C
6
aminoalkyl radical whose amine is protected by a (C
1
-C
6
alkyl)carbonyl, carbamyl or (C
1
-C
6
alkyl)sulphonyl radical; where two of the radicals R
7
, R
8
and R
9
may also form, together with the nitrogen atom to which they are attached, a 5- or 6-membered saturated ring containing carbon or containing at least one additonal heteroatoms, such as, for example, a pyrrolidine ring, a piperidine ring, a piperazine ring or a morpholine ring, it being possible for the said ring to be unsubstituted or substituted by a halogen atom, a hydroxyl radical, a

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