Oxidation bases containing a guanidine chain, process for...

Details Oxidation bases containing a guanidine chain, process for... Oxidation bases containing a guanidine chain, process for...

2001-01-29

2003-11-25

Kopec, Mark (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S406000, C008S407000, C008S408000, C008S409000, C008S410000

Reexamination Certificate

active

06652600

ABSTRACT:

The present invention relates to novel oxidation bases containing a benzene nucleus and comprising a guanidine chain, to a process for their preparation, to their use for the oxidation dyeing of keratin fibers, to dye compositions containing them and to oxidation dyeing processes using them.
It is known practice to dye keratin fibers, and in particular human hair, with dye compositions containing oxidation dye precursors, in particular ortho-phenylenediamines, para-phenylenediamines, ortho-aminophenols or para-aminophenols and heterocyclic compounds, which are generally referred to as oxidation bases. The oxidation dye precursors, or oxidation bases, are colorless or weakly colored compounds which, when combined with oxidizing products, can give rise to colored compounds and dyes by 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 chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds.
The variety of molecules used as oxidation bases and couplers makes it possible to obtain a wide range of colors.
The so-called “permanent” coloration obtained by means of these oxidation dyes should generally satisfy a certain number of requirements. For example, it should have no toxicological drawbacks and it should allow shades of the desired color strength to be obtained and have good resistance to external agents, such as light, bad weather, washing, permanent-waving, perspiration and friction.
The dyes should also allow white hairs to be covered, and, lastly, they should be as unselective as possible, i.e., they should allow the smallest possible differences in coloration to be produced over the entire length of the same keratin fiber, which may indeed be differently sensitized (i.e., damaged) between its end and its root.
Many patents disclosing novel hair dyes containing a benzene nucleus have been published in the literature. Among the most recent, mention may be made, in particular, of the pyrrolidine derivatives disclosed in U.S. Pat. No. 5,851,237, the polyol derivatives disclosed in Japanese patent application no. JP 11-158 046 or piperazine derivatives, such as those disclosed in German patent application no. DE 197 28 335.
However, in the field of oxidation dyes, the dyeing properties such as the remanence with respect to the various attacking factors and the various treatments to which keratin fibers may be subjected, and also the variety of shades obtained after reaction with various couplers, still remain to be improved.
The inventors have now discovered, entirely surprisingly and unexpectedly, that novel compounds containing a benzene nucleus comprising a guanidine chain, of formula (I) defined below, are not only suitable for use as oxidation bases, but also make it possible to obtain dye compositions which give intense colorations, over a broad range of colors, and have excellent properties of fastness (remanence) to the various treatments to which keratin fibers may be subjected. This remanence is significantly greater than that generally of the prior art.
These discoveries form the basis of the present invention.
A first subject of the invention is thus novel compounds of formula (I) below, and the addition salts thereof with an acid:
wherein:
X
1
and X
2
are each independently chosen from a hydroxyl group, —NHR
1
groups and
—NR
1
R
2
groups, wherein X
1
and X
2
are not simultaneously both hydroxyl groups;
R
1
and R
2
, which may be identical or different, are each chosen from hydrogen atoms,
C
1
-C
8
alkyl groups, C
1
-C
8
monohydroxyalkyl groups, C
2
-C
8
polyhydroxyalkyl groups, C
2
-C
8
aminoalkyl groups, mono(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl groups,
di(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl groups and C
1
-C
8
haloalkyl groups; when either X
1
or X
2
represents a group —NR
1
R
2
, then R
1
and R
2
can optionally form together, in combination with the nitrogen atom to which they are attached, an aromatic or non-aromatic 4-, 5- or 6-membered ring;
R
1
and R
2
, are each independently chosen from aromatic 4-, 5- and 6-membered rings and non-aromatic 4-, 5- and 6-membered rings, wherein said rings may comprise at least one heteroatom;
A is a divalent group chosen from —CH═N— and —CH
2
—NH—;
Z is a group chosen from a hydrogen atom, a halogen atom, aromatic 4-, 5- and 6-membered rings, non-aromatic 4-, 5- and 6-membered rings, C
1
-C
8
alkyl groups, C
1
-C
8
monohydroxyalkyl groups, C
2
-C
8
polyhydroxyalkyl groups, C
2
-C
8
aminoalkyl groups, mono(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl groups, di(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl groups, C
1
-C
8
haloalkyl groups, and —BR
3
groups wherein B is a divalent group chosen from the following groups:
and wherein R
3
is chosen from C
1
-C
8
alkyl groups, C
1
-C
8
monohydroxyalkyl groups, C
2
-C
8
polyhydroxyalkyl groups, C
2
-C
8
aminoalkyl groups, mono(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl groups, di(C
1
-C
4
)alkylamino(C
1
-C
4
)alkyl groups and C
1
-C
8
haloalkyl groups.
As indicated above, the dyes obtained with the compound(s) of formula (I) in accordance with the invention are powerful and make it possible to obtain a wide range of colors. Furthermore, they have excellent fastness properties with respect to the action of various external agents, such as light, bad weather, washing, permanent-waving, perspiration and friction.
In formula (I) above, the alkyl groups are chosen from linear groups and branched groups.
In formula (I) above, when R
1
and R
2
form, together with the nitrogen atom to which they are attached, a 4-, 5- or 6-membered ring, or when R
1
and/or R
2
represent a 4-, 5- or 6-membered ring, or when Z is an aromatic or non-aromatic 4-, 5- or 6-membered ring, then the said rings may bear one or more substituents which may be chosen, for example, from the following groups: hydroxyl groups, amido groups, halogen atoms, cyano groups, C
1
-C
8
alkyl groups, aromatic C
4
, C
5
and C
6
rings and non-aromatic C
4
, C
5
and C
6
rings.
Embodiments of compounds of formula (I) include the following compounds:
5-amino-2-hydroxy-benzylideneamino-guanidine,
2-amino-5-hydroxy-benzylideneamino-guanidine,
2,5-diamino-benzylideneamino-guanidine,
5-dihydroxyethylamino-2-hydroxy-benzylideneamino-guanidine,
5-dimethylamino-2-hydroxy-benzylideneamino-guanidine,
2-dihydroxyethylamino-5-hydroxy-benzylideneamino-guanidine,
2-dimethylamino-5-hydroxy-benzylideneamino-guanidine,
2-dihydroxyethylamino-5-amino-benzylideneamino-guanidine,
5-dihydroxyethylamino-2-amino-benzylideneamino-guanidine,
5-dimethylamino-2-amino-benzylideneamino-guanidine,
2-dimethylamino-5-amino-benzylideneamino-guanidine,
2-N-pyrrolidinyl-5-amino-benzylideneamino-guanidine,
5-N-pyrrolidinyl-2-amino-benzylideneamino-guanidine, and the addition salts thereof with an acid.
The addition salts with an acid of the compounds of formula (I) in accordance with the invention (mono- or disalification) may be chosen from inorganic salts and organic salts, such as hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates and acetates. For example, the addition salt may be chosen from the hydrochloride salts.
A subject of the invention is also a process for preparing the compounds of formula (I) in accordance with the invention, which comprises carrying out a direct coupling of the aminoguanidine with a benzaldehyde derivative whose substituents correspond to the compound of formula (I) which can be obtained, in an organic solvent such as an alcohol, to for instance ethanol, at a temperature ranging from 10° C. to the reflux temperature of said solvent. Said coupling may be followed by other reactions, for example a conventional reduction of a nitro group or a reduction of an imine function, leading to the expected compounds of formula (I). More details are given in the experimental section below.
When the synthesis is complete, the compounds of formula (I) in accordance with the invention may, if n

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