Use of novel indole compounds for dyeing and making up...

Details Use of novel indole compounds for dyeing and making up... Use of novel indole compounds for dyeing and making up...

2002-05-03

2004-02-17

Gupta, Yogendra N. (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S409000, C008S423000, C008S421000, C548S416000, C548S417000, C548S418000, C548S486000, C548S371400

Reexamination Certificate

active

06692538

ABSTRACT:

The invention relates to novel indole compounds, to their use as direct dyes in compositions intended for dyeing keratin materials and for example compositions intended for dyeing human keratin fibres and including the hair, and in cosmetic compositions intended for making up the skin, the nails and the lips, to the dye compositions and make-up compositions comprising them and to the corresponding direct dyeing process.
In the field of hair dyeing, direct dyes are sought, i.e. dyes which, without supplying an oxidizing agent, are capable by themselves of temporarily modifying the natural shade of the hair. In this application, the dyes may satisfy a certain number of criteria, and for example they may generate rich and varied shades making it possible to obtain a wide range of colours likely to satisfy the formulator; in this perspective, novel compounds are always being sought to be able to dye in a range of colours extending for example from orange to red. Moreover, the dyeing results obtained may be reproducible, strong and resistant to washing, rubbing, permanent-waving, light and perspiration.
The inventors have now discovered, entirely surprisingly and unexpectedly, novel indole compounds of formula (I) defined below, in the range of shades from orange to red, which are suitable for use as direct dyes in the dyeing of keratin materials, and in make-up compositions for the skin, the nails and the lips.
These novel dyes can also make it possible to obtain strong orange to red shades which show excellent properties of resistance to one or more of the various treatments to which keratin fibres may be subjected, and for example the hair, with respect to light, washing, permanent-waving and perspiration.
These discoveries form the basis of the present invention.
A first subject of the invention is thus a novel compound of formula (I):
wherein:
X, which may be identical or different, are each chosen from oxygen atoms and nitrogen atoms;
R
1
and R
2
, which may be identical or different, are each chosen from hydrogen atoms, C
1
-C
4
alkyl groups, C
1
-C
4
monohydroxyalkyl groups, C
1
-C
4
polyhydroxyalkyl groups, acyl( C
1
-C
4
alkyl carbonyl) groups, C
1
-C
4
aminoalkyl groups, C
1
-C
4
polyaminoalkyl groups and C
1
-C
4
aminohydroxyalkyl groups;
R
3
, R
4
and R
5
, which may be identical or different, are each chosen from hydrogen atoms and linear and branched, saturated and unsaturated C
1
-C
4
hydrocarbons.
In formula (I) according to the invention, said alkyl groups are chosen from linear groups and branched groups and include, for example, methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, isobutyl groups and tert-butyl groups; said C
1
-C
4
monohydroxyalkyl groups include, for example, —CH
2
—CH
2
OH groups and said C
1
-C
4
polyhydroxyalkyl groups include, for example, —CHOH—CH
2
OH groups.
Among the indole compounds of formula (I), the compound of formula (II) is an example:
A subject of the invention is also a process for manufacturing an indole compound of formula (I) according to the invention comprising oxidation of the corresponding indole in a solvent medium according to oxidation processes that are generally well known to those skilled in the art.
In this way, a compound of formula (III):
wherein R
1
, R
2
, R
3
, R
5
and X have the same meanings as defined in formula (I) above, may be oxidized in alcoholic medium (methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, for example). Additionally, said oxidation may be at room temperature. Further additionally, said oxidation may occur in the presence of sodium metaperiodate, to give a compound of formula (I) according to the invention.
Said sodium metaperiodate may also be replaced with appropriate sodium metaperiodate substitutes. Said substitutes may be chosen from, for example, molecular oxygen, hydrogen peroxide, potassium permanganate, selenium oxide and peracids. Said sodium metaperiodate and said appropriate substitutes may also be in the presence of metal catalysts which may be chosen from, for example, manganese, iron and chromium.
A subject of the invention is also a process for manufacturing an indole compound of formula (I) according to the invention, comprising oxidation of a compound of formula (III) described above in an alcoholic medium, in the presence of sodium metaperiodate, and at room temperature.
A subject of the invention is also a process of manufacturing a direct dye comprising including in said dyes at least one composition comprising at least one of said indole compounds of formula (I) according to the invention.
A subject of the invention is also a process of manufacturing make-up products comprising including in said make-up products at least one composition comprising at least one of said indole compounds of formula (I) according to the invention.
A subject of the invention is also a direct dye composition for keratin materials, comprising a medium suitable for dyeing and an effective amount of at least one compound of formula (I) according to the invention.
A subject of the invention is also a make-up product composition for keratin materials, comprising a medium suitable for make-up products and an effective amount of at least one compound of formula (I) according to the invention.
For the purposes of the present invention, the expression “keratin materials” mainly means the skin of the face and the body, the lips, the nails, at least one human keratin fiber such as human hair, body hairs, eyelashes and eyebrows, and also at least one keratin fiber such as natural textile fibers, including wool.
A subject of the invention is, for example, a direct dye composition for human keratin fibers such as the hair, comprising a medium suitable for dyeing and an effective amount of at least one compound of formula (I) according to the invention.
However, other non-limiting characteristics, aspects and advantages of the invention will emerge even more clearly on reading the description which follows, as well as the various concrete, but in no way limiting, examples intended to illustrate it.
When said composition is intended for dyeing, the compound(s) of formula (I) according to the invention can be each chosen from a range from approximately 0.05% to approximately 10% by weight relative to the total weight of the dye composition, and also from a range from approximately 0.05% to approximately 0.5% by weight relative to this weight.
When said composition is intended for make-up, the compound(s) of formula (I) according to the invention can be each chosen from a range from approximately 0.05% to approximately 20% by weight relative to the total weight of said composition, and also from a range from approximately 0.05% to approximately 5% by weight relative to this weight.
The compounds of formula (I) according to the invention can also serve, in well-known processes of oxidation dyeing of human keratin fibers, using oxidation dyes (oxidation dye precursors and optionally couplers), to shade the dyeing results obtained with the oxidation dyes or to enrich them with glints.
The dye composition according to the invention can also comprise, to broaden the range of shades and to obtain varied colours, besides the orange to red compounds of formula (I) according to the invention, other direct dyes conventionally used, for example nitrobenzene dyes, such as nitrophenylenediamines, nitrodiphenylamines, nitroanilines, nitrophenol ethers and nitrophenols, nitropyridines, anthraquinone dyes, monoazo dyes, diazo dyes, triarylmethane, azine, acridine and xanthene dyes, and alternatively metalliferous dyes.
The proportion of other additional said direct dyes can range from approximately 0.5% to approximately 10% by weight relative to the total weight of the dye composition.
The medium which is suitable for dyeing (or support) may generally comprise water or of a mixture of water and at least one organic solvent to dissolve compounds which may not be sufficiently soluble in water. Organic solvents which can be added to said composition, for examp

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