Direct hair dyes and use thereof

Details Direct hair dyes and use thereof Direct hair dyes and use thereof

2002-08-15

2004-12-28

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S636000, C008S643000, C008S407000, C552S208000

Reexamination Certificate

active

06835211

ABSTRACT:

This invention relates to preparations containing special substantive dyes for coloring and tinting keratin fibers, more especially human hair, to the use of these preparations and to new dyes.
Preparations for tinting and coloring hair are an important type of cosmetic product. They may be used to give the natural color of the hair a light or relatively dark shade, to obtain a totally different hair color or to cover unwanted color tones, for example gray tones, according to the wishes of the particular user. Conventional hair colorants are formulated either on the basis of oxidation dyes or on the basis of substantive dyes according to the required color or the permanence thereof. In many cases, combinations of oxidation dyes and substantive dyes are also used to obtain special shades.
Good dyes are distinguished by high coloring strength. They are also required to show high fastness to perspiration, heat, permanent waving, washing and light. In addition, they are expected to be toxicologically and dermatologically safe. It is also of advantage if the substances are highly soluble in various basic formulations.
Colorants based on oxidation dyes lead to bright and permanent color tones. However, they do involve the use of powerful oxidizing agents such as, for example, hydrogen peroxide solutions. This can damage the hair to be colored. Such damage then has to be repaired with suitable hair-care products. In addition, contact of the skin with these colorants can produce unwanted reactions in very sensitive people.
Colorants based on substantive dyes do not require oxidizing agents and can be better formulated at pH values around the neutral point. However, a major disadvantage of colorants based on substantive dyes is the poor fastness to washing of the colors obtained.
Among the substantive dyes, nitrobenzene derivatives play an important role. Nitroanilines and their derivatives in particular are distinguished by intensive colors with good fastness to light. However, a disadvantage of known nitroaniline dyes is their unsatisfactory fastness to washing, i.e. the colors lose intensity after repeated washing of the hair.
Accordingly, there is still a need for new substantive dyes distinguished by improved absorption onto the hair and/or by colors with improved fastness to washing.
In addition, substantive dyes are also used for shading purposes in oxidation hair colors. Accordingly, substantive dyes are expected to be highly compatible with oxidation dye precursors and with the components typically present in oxidation hair colorants. In particular, stability to reducing and oxidizing agents is desirable for an applicationally valuable substantive dye.
To develop fashionable colors, red color tones have to be obtained. This is frequently achieved by the use of 2-nitro-p-phenylenediamine derivatives. However, these derivatives are often inadequately soluble or dispersible in water. If the dye cannot be solubilized in the coloring medium, uneven colors are the result. There is also a high risk of only weak colors being obtained. In the particular case of colorants containing a high concentration of dyes or colorants containing carriers with only a weak solubilizing effect, the dyes crystallize out, remain in the coloring bath or are not sufficiently absorbed onto the hair.
It has now surprisingly been found that special hydroxyanthraquinone derivatives satisfy the requirements substantive dyes are expected to meet to a high degree.
Some hydroxyanthraquinone derivatives are already known to the expert as hair dyes from DE 32 07 036 A1. However, there is nothing in that document which points towards the hair dyes according to the present invention.
In a first embodiment, therefore, the present invention relates to preparations for coloring and tinting keratin fibers, more particularly human hair, which contain at (east one hydroxyanthraquinone derivative corresponding to formula (I):
in which R stands for a group corresponding to formula (II):
in which R
1
to R
4
independently of one another represent hydrogen, a hydroxy group, a C
1-4
alkoxy group, a C
1-4
alkyl group, a C
1-4
fluoroalkyl group, a carboxy group, a nitro group, a halogen atom, a group with the formula —S—R
5
, where R
5
is hydrogen or a C
1-4
alkyl group, a group with the formula —Ph—CH
2
—COOR
6
, where R
6
is hydrogen, a C
1-4
alkyl group or a physiologically acceptable cation, or two adjacent substituents R
1
to R
4
form a methylenedioxy ring and X is a halogen atom, as a substantive dye in a cosmetically acceptable carrier.
Examples of the C
1-4
alkyl groups mentioned as substituents in the compounds according to the invention are the methyl, ethyl, propyl, isopropyl and butyl groups. Ethyl and methyl are preferred alkyl groups. According to the invention, a preferred C
1-4
alkoxy group is, for example, a methoxy group or an ethoxy group. According to the invention, examples of a halogen atom are an F, Cl or Br atom, a Cl atom being particularly preferred. According to the invention, a preferred fluoroalkyl group is the trifluoromethyl group. Examples of physiologically acceptable cations are the cations of sodium, potassium and lithium and the ammonium ion. The sodium cation and the ammonium ion are particularly preferred. According to the invention, the abbreviation —Ph— stands for a disubstituted phenyl ring.
According to the invention, compounds of formula (I) in which X is a chlorine atom are preferred.
Other preferred compounds of formula (I) are those in which at least one of the substituents R
1
to R
4
is a hydroxy group, a methyl group or a methoxy group.
Particularly preferred compounds of formula (I) are 1,4-dihydroxy-6-chloro-7-phenoxyanthraquinone, 1,4-dihydroxy-6-chloro-7-(3′-hydroxyphenoxy)-anthraquinone, 1,4-dihydroxy-6-chloro-7-(3′-methoxyphenoxy)-anthraquinone, 1,4-dihydroxy-6-chloro-7-(3′-methylphenoxy)-anthraquinone, 1,4-dihydroxy-6-chloro-7-(2′-methyl-3′-hydroxyphenoxy)-anthraquinone, 1,4-dihydroxy-6-chloro-7-(4′-methylphenoxy)-anthraquinone, 1,4-dihydroxy-6-chloro-7-(3′,5′,-dimethoxyphenoxy)-anthraquinone, 1,4-dihydroxy-6-chloro-7-(2′,3′-dimethoxyphenoxy)-anthraquinone, 2-benzo-[3,4-d]-1,3-dioxolan-5-yloxy-3-chloro-5,8-dihydroxynaphthalene-1,4-dione and 1,4-dihydroxy-6-chloro-7-(2′-methylphenoxy)-anthraquinone.
The preparations according to the invention contain the compound of formula (I) in quantities of typically 0.05 to 5.0% by weight, based on the colorant, in the case of oxidation colorants without the oxidizing preparation. Quantities of 0.1 to 3% by weight are preferred.
In principle, there are no limitations to the usability of the compounds of formula (I) in preparations for coloring and tinting keratin fibers.
In a first preferred embodiment, the preparations according to the invention are preparations intended to produce only temporary coloring of the fibers. Corresponding preparations are commonly known as tinting preparations. This embodiment also encompasses, for example, hair treatment preparations with which the hair is intended to be not only temporarily colored, but also given a certain style. Corresponding preparations are known as tinting lotions.
Since the preparations in question can normally be formulated without the assistance of oxidizing components, especially hydrogen peroxide, the preparations according to the invention in this embodiment may be free from oxidation dye precursors.
Although the compounds corresponding to formula (I) may also be used as sole dye component, the preparations according to this embodiment preferably still contain at least one other dye of the substantive type.
Substantive dyes are normally nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols. Preferred substantive dyes are the compounds known under the International names or trade names of HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, Basic Yellow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HC Blue 2, HC Blue 12, Disperse Blue 3, Basic Blue

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