Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2003-07-09
2004-05-18
Mruk, Brian P. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S406000, C008S410000, C008S412000, C008S423000, C008S455000, C008S568000, C008S688000
Reexamination Certificate
active
06736862
ABSTRACT:
This invention relates to new indole/indoline hybrid dyes and hybrid dye precursors which are particularly suitable for coloring keratin fibers, to the use of these dyes and dye precursors and to colorants containing these dyes and/or dye precursors.
BACKGROUND OF THE INVENTION
Among the various products available for the cosmetic treatment of the human body, formulations for modifying or shading the color of the hair occupy a prominent position. Disregarding blonding preparations which lighten the hair oxidatively by degrading the natural hair dyes, three types of colorants have long been of importance in the coloring of hair:
So-called oxidation colorants are used for permanent, intensive colors with corresponding fastness properties. 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 under the influence of oxidizing agents or atmospheric oxygen.
Colorants or tints containing substantive dyes as their coloring component are normally used for temporary colors. Substantive dyes are based on dye molecules which are directly absorbed onto the hair and do not require an oxidative process for developing the color. Dyes such as these include, for example, henna which has been used since ancient times for coloring the body and hair.
In recent years, a new coloring process has received considerable attention. In this process, precursors of the natural hair dye, melanin, more particularly derivatives of indole or indoline, are applied to the hair and then form virtually “nature-identical” dyes in the hair in the course of oxidative processes. One such process using 5,6-dihydroxyindolines as the dye precursors is described in EP-B1 530 229. If preparations containing 5,6-dihydroxyindoline are applied, in particular repeatedly, people with gray hair can be given back their natural hair color. Color development can be carried out with atmospheric oxygen as sole oxidizing agent so that no other oxidizing agent has to be used.
Although it is possible in principle to formulate colorants containing only a dye or a dye precursor, such colorants are of only limited significance in practice with the exception of a few products which contain melanin precursors for example.
Instead, commercial hair coloring products normally contain a mixture of about 3 to 8 different dyes and/or dye precursors. However, the individual dyes generally differ in their capacity to be absorbed onto the hair and in their fastness to light, perspiration, rubbing and washing which, in addition, can be determined to a considerable extent by the structural properties and condition of the hair. These differences are pronounced above all when substantive dyes are used for adjusting the shade in oxidation hair colorants, as has hitherto been essential for many shades.
Accordingly, there is often a need in the development of new hair colorants to carry out extensive tests not only to obtain certain shades, but above all to ensure that the color is stable for the required period both in regard to shade and in regard to intensity.
SUMMARY OF THE INVENTION
It has now surprisingly been found that many of the problems mentioned above can be completely or at least partly avoided by the use of substances which possess both the properties of a melanin precursor and the properties of an oxidation dye precursor or any other melanin precursor. In particular, it has been found that the dyes have a very high capacity for absorption onto the hair comparable with that of known hair dyes or hair dye precursors and lead to brilliant intensive hair colors. By virtue of the molecular linkage, the problem of differing fastness properties of the two dyes or dye precursors can thus largely be overcome in many cases.
Substances such as these usable in hair colorants, which are referred to hereinafter as “hybrid dyes”, are new.
DETAILED DESCRIPTION OF THE INVENTION
In a first embodiment, therefore, the present invention relates to indole/indoline hybrid dyes and hybrid dye precursors, more particularly for coloring keratin fibers, which correspond to formula (I):
X—S—Y (I)
where
X is a group derived from an indole or indoline derivative as a melanin precursor,
Y is a group derived from
an oxidation dye precursor of the secondary or primary intermediate type or
an indole or indoline derivative as a melanin precursor; and
S is a structural element which is common constituent of the groups X and Y, a direct bond or at least one spacer group.
The compounds corresponding to formula (I) are obtainable by standard synthesis methods of organic chemistry. In this connection, reference is specifically made to the Synthesis Examples in the following.
As mentioned above, the structural principles of known classes of dyes form the basis of the newly developed hybrid dyes.
The group X is derived from a precursor of melanin selected from the derivatives of indole and indoline. In the context of the present invention, “precursors of melanin” are understood to be derivatives of indole and indoline which are capable of forming melanin dyes or corresponding melanin dye derivatives in an oxidative process.
According to the invention, the groups X in this embodiment are derived from indoles and indolines which contain at least one hydroxy and/or amino group, preferably as a substituent on the six-membered ring. These groups may carry other substituents, for example in the form of etherification or esterification of the hydroxy group or alkylation of the amino group. Indoles and indolines containing two of these groups, particularly two hydroxy groups, of which one or both may be etherified or esterified are particularly preferred.
According to the invention, particularly preferred groups X are derived from derivatives of indoline, such as 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline, 5,6-dihydroxyindoline-2-carboxylic acid, 5-hydroxyindoline, 6-hydroxyindoline, 5-aminoindoline, 6-aminoindoline and 4-aminoindoline.
Most particularly preferred groups X are derivatives of 5,6-dihydroxyindoline corresponding to formula (IIa):
in which—independently of one another
R
1
is hydrogen, a C
1-4
alkyl group, a C
1-4
hydroxyalkyl group, a C
3-6
cycloalkyl group, a vinyl group or an allyl group,
R
2
is hydrogen or a —COOH group which may even be present as a salt with a physiologically compatible cation,
R
3
is hydrogen or a C
1-4
alkyl group,
R
4
is hydrogen, a C
1-4
alkyl group or a group —CO—R
6
where R
6
is a C
1-4
alkyl group or an optionally substituted phenyl group and
R
5
stands for one of the groups mentioned for R
4
.
According to the invention, preferred representatives are 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxy-indoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline. The parent compound, 5,6-dihydroxyindoline, is most particularly preferred.
According to the invention, preferred indoles from which the group X is derived are 5,6-dihydroxyindole, N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihydroxy-indole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole, 5,6-dihydroxyindole-2-carboxylic acid, 5-hydroxyindole, 6-hydroxyindole, 5-aminoindole, 6-aminoindole and 4-aminoindole.
Particular preference is attributed to derivatives of 5,6-dihydroxyindole corresponding to formula (IIb):
in which—independently of one another
R
1
is hydrogen, a C
1-4
alkyl group, a C
1-4
hydroxyalkyl group, a C
3-6
cycloalkyl group, a vinyl group or allyl group,
R
2
is hydrogen or a —COOH group which may even be present as a salt with a physiologically compatible cation,
R
3
is hydrogen, a C
1-4
alkyl group or a group —CH
2
—NR
7
R
8
, where R
7
and R
8
independently of one another are hydrogen or a C
1-4
alkyl group,
R
4
is hydrogen, a C
1-4
alkyl group or a group —CO—R
6
where R
6
is a C
1-4
alkyl group or
Hoeffkes Horst
Hollenberg Detlef
Naumann Frank
Rose David
Elhilo Eisa
Harper Stephen D.
Henkel Kommanditgesellschaft auf Aktien
Hill Gregory M.
Mruk Brian P.
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