Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1999-08-31
2002-05-21
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S423000, C008S424000, C546S167000, C546S168000, C546S173000, C546S177000
Reexamination Certificate
active
06391064
ABSTRACT:
The invention relates to the use of derivatives of quinoline- or quinoxaline-5,8-diones or -diols in cosmetics, especially for the dyeing of keratinous matter and, in particular, the hair. It also relates to novel compounds of this class. The invention is also directed to dyeing compositions comprising the said compounds and to the method of dyeing keratinous fibres.
In the literature, adducts of pyrrole compounds and N,N-dialkylarylamines or N-alkylarylamines with quinoline-5,8-diones are known.
Thus J. Griffiths and C. Blackburn, in the journal
J. Chem. Res
. (
S
), 1982, pages 320-321, the disclosure of which is incorporated by reference herein, studied the reactions of 1,4-naphthoquinone and its derivatives with N,N-dialkylarylamines.
In the articles by K. Yoshida et al.,
Bull. Chem. Soc. Jpn
., 1988, 61, pages 4335-4340, and
Chem. Lett
., 1987, pages 1191-1194, the disclosures of each which are incorporated by reference herein, it was shown that, in the absence of metal salts, the reaction of quinoline-5,8-dione with N,N-dialkylarylamines was slow and led to isomer mixtures of 6- and 7-[p-(dialkylamino)phenyl]quinoline-5,8-dione whereas, in the presence of metal salts, only the compounds arylated in position 6 were obtained. The reactions are generally conducted in acetic acid; in certain cases, a chloroform-ethanol/HCl mixture can also be used, according to the article by K. Yoshida et al. in
Chem. Lett
., 1991, 2027-2030, the disclosure of which is incorporated by reference herein.
K. Yoshida et al. in
J. Chem. Soc. Perkin Trans. I
, 1992, 2713-2715, the disclosure of which is incorporated by reference herein, also studied the dioxo-5,8-quinolylpyrroles for their physiological properties and their colouring properties on an unspecified substrate. Furthermore, in the journal
J. Chem. Soc. Perkin Trans. I
, 1994, pages 2521-2523, the disclosure of which is incorporated by reference herein, K. Yoshida et al. took an interest in quinoline-5,8-diones carrying a substituent in position 6, for the purpose of a utility as a precursor of dyes which can be used in optoelectronics.
Furthermore, the only known derivative of quinoxaline corresponds to the following formula:
In accordance with the above text, adducts of pyrrole compounds and N,N-dialkylarylamines or N-alkylarylamines with quinoline-5,8-diones are already known, but no allusion whatsoever is made as regards their application in cosmetics.
On the other hand, the addition compounds of indoles with quinolinediones or quinoxalines are novel.
In the field of hair dyeing, dyes are sought which are reproducible, with rich and varied shades, thereby making it possible to obtain a wide pallet of colours capable of satisfying the formulator.
The inventors have now discovered that a new class of derivatives of quinoline- or quinoxaline-5,8-diones or -diols can be used for the dyeing of keratinous matter and, in particular, the hair. This new class, which is the subject of the invention, satisfies the above-described objectives and, moreover, is highly accessible, since the majority of these dyes are prepared in a single stage which is easy to implement.
The dyeings obtained with the aid of these dyes can exhibit reproducible, intensive and varied shades.
The present invention therefore provides for the use of compounds of general formulae (I) and (II) defined below in the dyeing of keratinous matter and, in particular, of the hair.
The present invention also provides novel compounds of this class.
The invention additionally provides dyeing compositions and a method of dyeing which employs them.
Other features, aspects and advantages of the invention will appear more clearly still on reading the description and various examples which follow.
One subject of the present invention is the use in the dyeing of keratinous matter and, in particular, of the hair of compounds of general formulae (I) and (II):
in which:
Q represents the groups
X represents the group CH or a nitrogen atom;
T represents a hydrogen atom, a halogen atom or a hydroxyl group;
R
1
, R
2
, R
3
, R
4
and R
5
, which are identical or different, are selected from a hydrogen atom, C
1
-C
4
alkoxy groups, amino groups —N(W
1
)(W
2
), groups —NH—CO—W
1
, groups —O—CO—W
1
, a hydroxyl group, a carboxylic acid group, derivatives of a carboxylic acid group, such as esters, amides, mineral salts, and organic amine salts, halogen atoms, linear and branched C
1
-C
4
alkyl groups optionally substituted by a substituent selected from nitrile groups, a carboxylic acid group, derivatives of a carboxylic acid group, such as esters, amides, mineral salts, and organic amine salts, a hydroxyl group, groups such as:
ether groups —OSi(W
1
)
3
, amino groups
and amido groups
or
Z is selected from a hydrogen atom, a benzyl group, a phenyl group optionally substituted by a substituent selected from a hydroxyl group, groups —O—CO—W
1
, amino groups —N(W
1
)(W
2
), groups —NH—CO—W
1
and a nitrile group; linear and branched C
1
-C
8
alkyl groups optionally substituted by a substituent selected from a nitrile group, a carboxylic acid group, derivatives of a carboxylic acid group, such as esters, amides, mineral salts, and organic amine salts, a hydroxyl group, groups such as:
ether groups —OSi(W
1
)
3
, amino groups
and amido groups
or
W
1
and W
2
, which are identical or different, are selected from a hydrogen atom and linear and branched C
1
-C
4
alkyl groups,
W
3
and W
4
, which are identical or different, are selected from a hydrogen atom and linear and branched C
1
-C
4
alkyl groups optionally substituted by at least one substituent selected from a hydroxyl group, groups —CO—O—W
1
, groups —O—CO—W
1
, and amino groups —N(W
1
)(W
2
).
The C
1
-C
4
alkyl groups or the C
1
-C
4
alkyl moieties of alkoxy groups can be linear or branched and are selected in particular from the groups methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl, preferably from the groups methyl, ethyl and n-butyl.
The C
1
-C
8
alkyl groups can be linear or branched; they can be substituted by a nitrile group, a carboxylic acid group or its derivatives such as esters, amides, mineral salts and organic amine salts, a hydroxyl group, an ester group such as alkoxycarbonyl, carboxyl, alkylcarbonyloxy, formyloxy, tosyloxy, an amino group, an amido group such as aminocarbonyl or acetamido, or an ether group selected from trialkylsiloxy and siloxy groups.
These C
1
-C
8
alkyl groups are selected in particular from the groups methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl and octyl, and preferably from the groups methyl and pentyl.
The halogen atoms are selected from chlorine, bromine, fluorine and iodine, and in particular chlorine.
Among the compounds of formulae (I) and (II) defined above, mention may be made in particular of the following compounds:
6-(1-pentyl-1H-pyrrol-2-yl)quinoline-5,8-dione,
6-(1-benzyl-1H-pyrrol-2-yl)quinoline-5,8-dione,
methyl 4-(5,8-dioxo-5,8-dihydroquinolin-6-yl)-2,5-dimethyl-1H-pyrrole-3-carboxylate,
N-[2-[2-(5,8-dioxo-5,8-dihydroquinolin-6-yl)pyrrol-1-yl]ethyl]acetamide,
6-(1-phenyl-1H-pyrrol-2-yl)quinoline-5,8-dione,
3-[2-(5,8-dioxo-5,8-dihydroquinolin-6-yl)pyrrol-1-yl]propionitrile,
6-chloro-7-(1-methyl-1H-pyrrol-2-yl)quinoline-5,8-dione,
6-(1,2-dimethyl-1H-indol-3-yl)quinoline-5,8-dione,
6-(1-benzyl-1H-indol-3-yl)quinoline-5,8-dione,
6-(2-phenyl-1H-indol-3-yl)quinoline-5,8-dione,
6-(2-methyl-1H-indol-3-yl)quinoline-5,8-dione,
6-(2-methyl-1H-indol-3-yl)quinoline-5,8-dione,
6-[p-(N,N-(2-diacetyloxyethyl)amino)phenyl]-quinoline-5,8-dione,
6-(1-methyl-1H-pyrrol-2-yl)quinoxaline-5,8-dione,
6-(1-methyl-1H-pyrrol-2-yl)quinoline-5,8-dione,
7-(1-methyl-1H-pyrrol-2-yl)quinoline-5,8-dione,
6-[p-(N,N-diethylamino)phenyl]quinoline-5,8-dione,
6-[p-(N,N-dimethylamino)phenyl]quinoline-5,8-dione
7-[p-(N,N-dimethylamino)phenyl]quinoline-5,8-dione
6-[4-(N,N-diethylamino)-3-isopropenylphenyl]-quinoline-5,8-
Baudry Richard
Genard Sylvie
Maignan Jean
Einsmann Margaret
L'Oreal (S.A.)
LandOfFree
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