Aminophenol derivatives and their use in oxidative hair dyes

Details Aminophenol derivatives and their use in oxidative hair dyes Aminophenol derivatives and their use in oxidative hair dyes

1999-01-22

2003-10-21

Killos, Paul J. (Department: 1621)

Drug, bio-affecting and body treating compositions

Live hair or scalp treating compositions

Hair coloring

C424S061000

Reexamination Certificate

active

06635241

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to new aminophenol derivatives, to their use for coloring keratin fibers and to colorants containing these compounds.
DESCRIPTION OF THE INVENTION
By virtue of their intensive colors and good fastness properties, so-called oxidation colorants play a prominent role in the coloring of keratin fibers, particularly human hair. Oxidation colorants normally contain oxidation dye precursors, so-called primary intermediates and secondary intermediates. The primary intermediates form the actual dyes with one another or by coupling with one or more secondary intermediates in the presence of oxidizing agents or atmospheric oxygen.
Good oxidation dye precursors are expected to satisfy above all the following requirements: they must form the required color tones with sufficient intensity and fastness during the oxidative coupling reaction. In addition, they must be readily absorbed onto the fibers with no significant differences—particularly in the case of human hair—between damaged and freshly regrown hair (levelling behavior). They must be resistant to light, heat and the effect of chemical reducing agents, for example permanent wave lotions. Finally, if they are used to color hair, they should not overly stain the scalp and, above all, should be toxicologically and dermatologically safe.
The primary intermediates normally used are primary aromatic amines containing another free or substituted hydroxy or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyridine and derivatives thereof.
Special representatives are, for example, p-phenylenediamine, p-toluylenediamine, 2,4,5,6-tetraaminopyrimidine. p-aminophenol, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 2-(2,5-diaminophenyl)ethanol, 2-(2,5-diaminophenoxy)-ethanol, 1-phenyl-3-carboxyamido-4-amino-5-pyrazolone, 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triamino-hydroxypyrimidine.
The secondary intermediates used are generally m-phenylenediamine derivatives, naphthols, resorcinols and resorcinol derivatives, pyrazolones and m-aminophenols. Particularly suitable secondary intermediates are &agr;-naphthol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenedi-amine, 1-phenyl-3-methyl-5-pyrazolone, 2,4-dichloro-3-aminophenol, 1,3-bis-(2,4-diaminophenoxy)-propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-amino-4-hydroxypyridine, 2-methyl resorcinol and 5-methyl resorcinol.
So far as other typical dye components are concerned, reference is expressly made to the Colipa list published by the Industrieverband Körperpflege und Waschmittel, Frankfurt.
Generally speaking, a natural-looking hair color cannot be obtained with a primary intermediate alone or with a special combination of primary and secondary intermediates. In practice, therefore, combinations of various primary intermediates and secondary intermediates are normally used. Because of this, there is a constant demand for new improved dye components.
Accordingly, the problem addressed by the present invention was to provide new primary intermediates which would satisfy the requirements oxidation dye precursors are expected to meet to a particular degree.
It has now been found that certain hitherto unknown aminophenol derivatives satisfy the requirements primary intermediates are expected to meet to a particularly high degree. Thus, brilliant color tones extremely resistant to light and washing are obtained using these primary intermediates with most of the known secondary intermediates. In addition, the colors obtained are distinguished by extreme fastness to cold waving and thermal stability and by excellent levelling.
In a first embodiment, therefore, the present invention relates to aminophenol derivatives corresponding to general formula (1):
in which one of the two substituents R
1
and R
2
is hydrogen and the other substituent is hydrogen, chlorine or fluorine and one of the two substituents R
3
and R
4
is
hydrogen,
a C
1-4
alkyl group, a C
1-4
alkoxy group
a C
1-4
hydroxyalkyl group, preferably with a terminal hydroxy group, or
halogen
and the other substituent is one of the following groups:
—O—CH
2
—CH═CH
2
,
—CH═CH—COOX, where X is hydrogen or a physiologically compatible inorganic or organic cation,
and, in the case of the substituent R
3
, a group corresponding to the following formula:
and, in the case of the substituent R
4
, a group corresponding to the following formula:
where -A- stands for one of the following groups:
These compounds may be prepared by known organic synthesis methods. So far as the details are concerned, reference is expressly made to the synthesis examples set out in detail in the Examples section.
Since all the compounds according to the invention are amino compounds, the known acid addition salts can be prepared from them by standard methods. Accordingly, all the disclosures of the present specification and, accordingly, the statement of claim relate both to the aminophenol derivatives (I) present in free form and to their water-soluble physiologically compatible salts. Examples of such salts are the hydrochlorides, hydrobromides, sulfates, phosphates, acetates, propionates, citrates and lactates.
The aminophenol derivatives of formula (I), where both R
1
and R
2
represent hydrogen, have proved to be particularly suitable for the purposes of the invention.
Compounds of formula (I), where one of the two substituents R
3
or R
4
is hydrogen, are also preferred for the purposes of the invention.
Among the compounds of formula (I) derived from cinnamic acid, the free acids, i.e. X═H, are preferred. However, the alkali metal, alkaline earth metal, aluminium, ammonium and mono-, di- and tri-C
1-4
-hydroxyalkyl ammonium salts may also be used for the purposes of the invention.
Finally, among the compounds representing hydroxyalkyl diethers, those in which R is a number of 1 to 6 and which contain a hydroxy group at the aliphatic chain, i.e. z=1, are preferred.
In the context of the invention as a whole, particularly suitable compounds are
bis-(5-amino-2-hydroxyphenyl)-methane,
3-hydroxy-6-aminoallyloxybenzene,
2-hydroxy-5-aminoallyloxybenzene,
5-amino-2-hydroxycinnamic acid,
bis-[2-(2-hydroxy-5-aminophenoxy)-ethyl]-ether,
1,8-bis-[2-hydroxy-5-aminophenoxy]-3,6-dioxaoctane,
1,3-bis-(2-hydroxy-5-aminophenoxy)-propane and
1,3-bis-(2-hydroxy-5-aminophenoxy)-propan-2-ol.
In a second embodiment, the present invention relates to the use of the aminophenol derivatives mentioned above as primary intermediates in oxidation hair colorants.
Finally, in a third embodiment, the present invention relates to oxidation colorants for coloring keratin fibers containing secondary intermediates and primary intermediates in a water-containing carrier, characterized in that they contain one of the above-mentioned aminophenol derivatives as primary intermediate.
Keratin fibers in the context of the invention include pelts, wool, feathers and, in particular, human hair. Although the oxidation colorants according to the invention are particularly suitable for coloring keratin fibers, there is in principle nothing to prevent them from being used in other fields, particularly in color photography.
The oxidation colorants according to the invention contain the primary intermediates according to the invention and, if desired, may contain other primary intermediates and secondary intermediates. So far as the other primary and secondary intermediates are concerned, reference is made to the substances mentioned at the beginning of the description which represent preferred other dye components. Particularly preferred other primary intermediates are 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, dihydroxyaminopyridines, 1-(&bgr;-hydroxyethyl)-2,5-diaminobenzene, p-phe

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