Cationic di-methylenedioxy-benzenes, their use for oxidation...

Details Cationic di-methylenedioxy-benzenes, their use for oxidation... Cationic di-methylenedioxy-benzenes, their use for oxidation...

2000-11-21

2002-06-11

Kopec, Mark (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dyeing involving animal-derived natural fiber material ,...

Hair dyeing

C008S406000, C008S408000, C008S409000, C008S554000, C008S570000, C008S573000, C549S437000, C549S438000

Reexamination Certificate

active

06402791

ABSTRACT:

The subject of the invention is novel dimethylenedioxybenzenes comprising at least one cationic group Z, Z being chosen from quaternized aliphatic chains, aliphatic chains comprising at least one quaternized saturated ring, and aliphatic chains comprising at least one quaternized unsaturated ring, their use as oxidation dye precursor for the oxidation dyeing of keratinous fibres, dyeing compositions containing them, as well as the oxidation dyeing methods using them.
It is known to dye keratinous fibres, and in particular human hair, with dyeing compositions containing oxidation dye precursors, in particular para-phenylenediamines, ortho- or para-aminophenols, heterocyclic compounds such as diaminopyrazole derivatives, generally called oxidation bases. Oxidation dye precursors, or oxidation bases, are colourless or weakly coloured compounds which, combined with oxidizing products, can give rise, by a process of oxidative condensation, to coloured and colouring compounds.
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 such as for example indolic couplers.
The variety of the molecules used in oxidation bases and couplers makes it possible to obtain a rich palette of colours.
The so-called “permanent” colour obtained using these oxidation dyes must moreover meet a number of requirements. Thus, it must be without drawbacks from the toxicological point of view, it must make it possible to obtain shades in the desired intensity and exhibit good resistance to external agents (light, adverse weather conditions, washing, permanent waving, perspiration, rubbing).
The dyes must also make it possible to cover grey hair, and be the least selective possible, that is to say make it possible to obtain the smallest possible differences in colour right along the same keratinous fibre, which may indeed be differently sensitized (i.e. damaged) between its tip and its root.
However, the Applicant has now just discovered, completely unexpectedly and surprisingly, that a novel family of dimethylenedioxybenzenes of formula (I) defined below, comprising at least one cationic group Z, Z being chosen from quaternized aliphatic chains, aliphatic chains comprising at least one quaternized saturated ring, and aliphatic chains comprising at least one quaternized unsaturated ring, is not only suitable for use as oxidation dye precursor for oxidation dyeing, but, in addition, that it makes it possible to obtain dyeing compositions leading to intense colours, in a very broad palette of shades and exhibiting excellent properties of resistance to different treatments to which the keratinous fibres may be subjected.
These discoveries form the basis of the present invention.
The first subject of the invention is therefore dimethylenedioxybenzenes of the following formula (I), and their addition salts with an acid:
in which:
B is a linking arm which represents a linear or branched alkyl chain preferably comprising from 1 to 14 carbon atoms, which may be interrupted by one or more groups Z as defined below and/or by one or more heteroatoms such as oxygen, sulphur or nitrogen atoms, and optionally substituted with one or more hydroxyl or C
1
-C
6
alkoxy radicals, and which may carry one or more ketone functions;
Ra, Rb, R′a and R′b, which are identical or different, may represent a hydrogen atom, a C
1
-C
6
alkyl radical, a C
1
-C
6
hydroxyalkyl radical, or form in pairs, together with the carbon atom to which they are attached, a 5-, 6- or 7-membered saturated carbon ring;
R
1
, R′
1
, R
2
, R′
2
, R
3
and R′
3
, which may be identical or different, represent a hydrogen atom; a halogen atom; one of the two valences of a linking arm B, a group Z as defined below; a group A
2
as defined below; a group A
2
′ as defined below; a (C
1
-C
6
)alkylcarbonyl radical; an amino(C
1
-C
6
)alkylcarbonyl radical; an N-Z-amino(C
1
-C
6
)alkylcarbonyl radical; an N-(C
1
-C
6
)alkylamino(C
1
-C
6
)alkylcarbonyl radical; an N,N-di(C
1
-C
6
alkyl)amino(C
1
-C
6
)alkylcarbonyl radical; an amino(C
1
-C
6
)alkylcarbonyl(C
1
-C
6
)alkyl radical; an N-Z-amino(C
1
-C
6
)alkylcarbonyl(C
1
-C
6
)alkyl radical; an N-(C
1
-C
6
alkyl)amino(C
1
-C
6
)alkylcarbonyl(C
1
-C
6
)alkyl radical; an N,N-di(C
1
-C
6
alkyl)amino(C
1
-C
6
)alkylcarbonyl(C
1
-C
6
)alkyl radical; a carboxyl radical; a (C
1
-C
6
)alkylcarboxyl radical; a (C
1
-C
6
)alkylsulphonyl radical; an aminosulphonyl radical; an N-Z-aminosulphonyl radical; an N-(C
1
-C
6
alkyl)aminosulphonyl radical; an N,N-di(C
1
-C
6
alkyl)aminosulphonyl radical; an aminosulphonyl(C
1
-C
6
)alkyl radical; an N-Z-aminosulphonyl(C
1
-C
6
)alkyl radical; an N-(C
1
-C
6
alkyl)aminosulphonyl(C
1
-C
6
)alkyl radical; an N,N-di(C
1
-C
6
alkyl)aminosulphonyl(C
1
-C
6
)alkyl radical; a carbamyl radical; an N-(C
1
-C
6
alkyl)carbamyl radical; an N,N-di(C
1
-C
6
alkyl)carbamyl radical; a carbamyl(C
1
-C
6
)alkyl radical; an N-(C
1
-C
6
alkyl)carbamyl(C
1
-C
6
)alkyl radical; an N,N-di(C
1
-C
6
alkyl)carbamyl(C
1
-C
6
)alkyl radical; 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
trifluoroalkyl radical; a cyano radical; a group OR
6
, OR′
6
, SR
6
or SR′
6
; a C
1
-C
6
aminoalkyl radical in which the alkyl is unsubstituted or substituted with one or more hydroxyl radicals; an amino(C
1
-C
6
)alkyl radical in which the alkyl is unsubstituted or substituted with one or more hydroxyl radicals and in which the amine is substituted with one or two radicals, which are identical or different, chosen from the alkyl, C
1
-C
6
monohydroxyalkyl, C
2
-C
6
polyhydroxyalkyl, (C
1
-C
6
)alkylcarbonyl, carbamyl, N-(C
1
-C
6
alkyl)carbamyl or N,N-di(C
1
-C
6
alkyl)carbamyl, C
1
-C
6
)alkylsulphonyl, formyl, trifluoro(C
1
-C
6
)alkylcarbonyl, (C
1
-C
6
)alkylcarboxyl or thiocarbamyl radicals, or from the groups Z as defined below, or which can form together, with the nitrogen atom to which they are attached, a 5- or 6-membered ring, containing carbon or containing one or more heteroatoms;
R
6
and R′
6
, which may be identical or different, denote one of the two valences of a linking arm B; a C
1
-C
6
alkyl radical; a C
1
-C
6
monohydroxyalkyl radical; a C
2
-C
6
polyhydroxyalkyl radical; a group Z as defined below; a (C
1
-C
6
)alkoxy(C
1
-C
6
)alkyl radical; an aryl radical; a benzyl radical; a C
1
-C
6
carboxyalkyl radical; a (C
1
-C
6
)alkylcarboxy(C
1
-C
6
)alkyl radical; a C
1
-C
6
cyanoalkyl radical; a C
1
-C
6
carbamylalkyl radical; an N-(C
1
-C
6
alkyl)carbamyl(C
1
-C
6
)alkyl radical; an N,N-di(C
1
-C
6
alkyl)carbamyl(C
1
-C
6
)alkyl radical; a C
1
-C
6
trifluoroalkyl radical; a C
1
-C
6
aminosulphonylalkyl radical; a C
1
-C
6
N-Z-aminosulphonylalkyl radical; an N-(C
1
-C
6
alkyl)aminosulphonyl(C
1
-C
6
)alkyl radical; an N,N-di(C
1
-C
6
alkyl)aminosulphonyl(C
1
-C
6
)alkyl radical; a (C
1
-C
6
)alkylsulphonyl(C
1
-C
6
)alkyl radical; a (C
1
-C
6
)alkylsulphonyl(C
1
-C
6
)alkyl radical; a (C
1
-C
6
)alkylcarbonyl(C
1
-C
6
)alkyl radical; an amino(C
1
-C
6
)alkyl radical; an amino(C
1
-C
6
)alkyl radical in which the alkyl is unsubstituted or substituted with one or more hydroxyl radicals and in which the amine is substituted with one or two radicals, which are identical or different, chosen from the (C
1
-C
6
)alkylmonohydroxy(C
1
-C
6
)alkyl, polyhydroxy(C
2
-C
6
)alkyl, (C
1
-C
6
)alkylcarbonyl, formyl, trifluoro(C
1
-C
6
)alkylcarbonyl, (C
1
-C
6
)alkylcarboxyl, carbamyl, N-(C
1
-C
6
alkyl)carbamyl, N,N-di(C
1
-C
6
alkyl)carbamyl, thiocarbamyl and (C
1
-C
6
)alkylsulphonyl radicals, and among the groups Z as defined below; or which can form, together with the nitrogen atom to which they are attached, a 5- or 6-membered ring containing carbon or containing one or more heteroatoms;
A
1
represents

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