DE2524329A1 - Hair dyeing compsns. contg. 5-amino 4,6-dioxo pyrimidine derivs. - as developers and standard couplers for oxidn. hair dyes - Google Patents

Abstract

Oxidn. dye-based hair dyeing compsns. contain (a), as developers, 5-amino-4,6-dioxo-pyrimidiene derivs., (I), having formula (Ia) or (Ib): (where R is H or -NR3R4; R1-R4 are H, 1-4C alkyl, 1-4C hydroxyalkyl, opt. substd. Ph or aralkyl, and R3 and R4 together with N to which they are linked can form 5- or 6-membered heterocyclic ring which may contain a further N- or O-atom), as well as their inorganic or organic salts, and (b) standard couplers used in oxidn. hair dyes. The hair dyeing compsns. are used in oxidn. hair dyes. The hair dyeing compsns. are used in cosmetic compsns., e.g. creams, emulsions, gels, or also solns. (I) form strong shades, ranging from yellow via brown, red and blue to violet; dyeings achieved are fast and can be easily stripped with reducing agents; (I) are soluble in water, stable to storage, non-toxic and do not irritate skin. (I) allow fully satisfactory dyeing to be achieved by oxidative coupling through air-O2, thus preventing hair-damage through chemical oxidising agents (which are however needed for lightening effect).

Description

"Hair dye" The invention relates to oxidative agents Hair coloring based on 5-amino-4,6-dioxo-pyrimidine derivatives as a developer component.

The so-called oxidation colors play a role in the coloring of hair, that by oxidative coupling of a developer component with a coupler component arise because of their intense colors and very good fastness properties preferred role. Nitrogen bases are usually used as developer substances such as p-phenylenediamine derivatives, diaminopyridines, 4-amino-pyrazolone derivatives, heterocyclic ones Hydrazones used. The so-called coupler components are m-phenylene-diamine derivatives, Phenols, naphthols, resorcinol derivatives and pyrazolones called.

Good oxidative hair dye components must primarily include the following Meet prerequisites: You must with the oxidative coupling with the respective Developer or coupler components the desired color nuances in sufficient Develop intensity. They must also have sufficient to very good absorbability on human hair and they are also said to be toxicological and be dermatologically harmless.

The class of compounds commonly used as developer substances the substituted or unsubstituted p-phenylenediamines has the disadvantage that they are sensitized in a number of people and severe in their wake Causes allergies. Another disadvantage is that they are difficult to restore are removable. The main purpose of avoiding these dermatological disadvantages in Recently proposed developer substances can be applied in their application Properties are not always fully satisfactory.

There was therefore a search for useful oxidation hair dyes the task of finding suitable components, the aforementioned requirements meet in an optimal way.

It has now been found that hair dyes based on oxidation dyes with a content of 5-amino-4,6-dioxo-pyrimidine derivatives of the general formula in which R can represent a hydrogen atom or the radical -NRDR4 and R1 - R4 a hydrogen atom, an alkyl radical with 1 - 4 carbon atoms, a hydroxyalkyl radical with 1 - 4 carbon atoms, a phenyl radical, substituted phenyl radical or aralkyl radical, furthermore R5 and R4 with the nitrogen atom to a 5- or 6-membered heterocyclic ring, which may contain a further nitrogen atom or oxygen atom, can be closed, as well as their inorganic or organic salts as developer substances and the coupler substances customary in oxidation hair dyes meet the requirements to a particularly high degree.

When used as developer components, those according to the invention provide Compounds with the coupler substances generally used for oxidation hair coloring the most varied of very intense color nuances, like those with these couplers and the previously known developers were not achievable and thus represent a essential enrichment of the oxidative hair coloring possibilities.

The 5-amino-4, 6-dioxopyrimidine derivatives according to the invention are also distinguished by very good fastness properties of the dyeings achieved therewith, by a good solubility in water, good storage stability and toxicological, as well dermatological harmlessness.

The 5-amino-4,6-dioxopyrimidine derivatives to be used as developer components according to the invention can either as such or in the form of their salts with inorganic or organic Acids such as B. as chlorides, sulfates, phosphates, acetates, propionates, lactates, Citrates are used.

The preparation of the components to be used according to the invention as developer components 5-Amino-4,6-dioxopyrimidine derivatives are already known from the literature. You can click on the take place in a wide variety of ways, as in the references given in the examples is described in more detail.

As developer components to be used according to the invention are, for. B. 5-amino-4,6-dioxo-3,4,5,6-tetrahydropyrimidine, 5-amino-4,6-dioxo-3-methyl-3,4,5,6-tetrahydropyrimidine J. 5-amino-4,6-dioxo-3-hydroxyethyl-3,4,5,6-tetrahydropyrimidine, 5-amino-3-phenyl-4,6-dioxo-3,4,5,6-tetrahydropyrimidine, 5-amino-4,6-dioxo-3-benzyl -), 4,5,6-tetrahydropyrimidine, 5-amino-4,6-dioxo-3-tolyl-3,4,5,6-tetrahydropyrimidine, 2,5-diamino-4,6-dioxo-3,4,5,6-tetrahydropyrimidine, 5-amino-2-dimethylamino-4,6-dioxo-3,4,5, 6-tetrahydropyrimidine, 5-amino-2-d-hydroxyethylamino-4,6-dioxo-3,4,5,6-tetrahydropyrimidine, 5-amino-2-anilino-4,6-dioxo-3,4,5,6-tetrahydropyrimidine, 5-amino-2-morpholino-4,6-dioxo-3,4,5,6-tetrahydropyrimidine, 5-amino-2-piperidino-4,6-dioxo-3,4,5,6-tetrahydropyrimidine, 5-amino-barbituric acid, 5-amino-1-methyl-barbituric acid, 5-amino-hydroxyethyl-barbituric acid, 5-amino-1 -phenyl-barbituric acid, 5-amino-1 -benzyl-barbituric acid, 5-amino-1 -tolyl-barbituric acid, 5-Amino-1,3-dimethyl-barbituric acid, 5-amino-1,3-diphenyl-barbituric acid should be mentioned.

As examples of those to be used in the hair colorants according to the invention Coupler components are i-naphthol, o-cresol, m-cresol, 2,6-dimethylphenol, 2,5-dimethylphenol, 3,4-dimethylphenol, 3,5-dimethylphenol, pyrocatechol, pyrogallol, 1,5- or. 1,7-dihydroxy-naphthalene, 5-amino-2-methylphenol, hydroquinone, 2,4-diamino-anisole, m-toluenediamine, 4-aminophenol, Resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-3-amino-pyrazolon-5, t-phenyl-3,5-diketo-pyrazolidine, 1-methyl-7-dimethyl-amino-4-hydroxy-quinolone-2, 1-amino-3-acet-acetylamino-4-nitro-benzene or 1-amino-3-cyanoacetyl-amino-4-nitrobenzene to cite.

The developer components are used in the hair dyes according to the invention generally in approximately molar amounts, based on the coupler substances used, used. If molar use also proves useful, so it is However, this is not disadvantageous if the developer component is in a certain excess or a shortfall is used.

It is also not necessary that the developer component and the coupler substance represent uniform products, rather both the Developer component Mixtures of the 5-amino-4,6-dioxo-pyrimidine derivatives to be used according to the invention as well as the coupler substance mixtures of the aforementioned coupler components represent.

In addition, the hair colorants of the invention can be others known and customary developer components, as well as, where appropriate, customary direct-drawing components Contain dyes in the mixture, if this is necessary to achieve certain color nuances is.

The oxidative coupling, i.e. H. the development of the color, can in principle As with other oxidation hair dyes, it is done by means of atmospheric oxygen. Appropriately However, chemical oxidizing agents are used. As such come in particular Hydrogen peroxide or its addition products with urea, melamine and sodium borate and mixtures of such hydrogen peroxide addition compounds with potassium peroxide disulfate into consideration.

The 5-amino-4,6-dioxopyrimidine derivatives according to the invention have as the developer component the advantage that they are fully satisfactory even with oxidative coupling by atmospheric oxygen Provide coloring results and thus a hair damage by the otherwise for the oxidative Coupling used oxidizing agents can be avoided. However, at the same time In addition to the coloring, if a lightening effect is desired on the hair, it should also be used of oxidizing agents required.

The hair dyes according to the invention are suitable for use in cosmetic preparations such as creams, emulsions, gels or simple solutions incorporated and immediately before application on the hair with one of the mentioned Oxidizing agents added. The concentration of such dyeing preparations of the coupler-developer combination is 0.2 to 5 percent by weight. For the production of creams, emulsions or gels are the coloring components with those for such Preparations mixed with other ingredients.

Such additional components are, for example, wetting agents or emulsifiers of the anionic or nonionic type such as alkylbenzenesulfonates, fatty alcohol sulfates, Alkyl sulfonates, fatty acid alkanolamides, addition products of io; ethylene oxide Fatty alcohols, thickeners such as methyl cellulose, starch, higher fatty alcohols, Paraffin oil, fatty acids, also perfume oils and hair care products, such as pantothenic acid and cholesterol. The additives mentioned are in the for this Usual amounts are used for purposes such as wetting and emulsifying agents in concentrations from 0.5 - 30 percent by weight and thickener in concentrations of 0.1 - 25th Percentage by weight, in each case based on the entire preparation.

The application of the hair colorants according to the invention can, independently whether it is a solution, an emulsion, a cream or a gel, in a weakly acidic, neutral or especially alkaline environment at a pH value from 8-10. The application temperatures are in the range of 15 to 40 ° C. After an exposure time of about 30 minutes, the hair dye is removed from the hair to be colored by rinsing. Afterwards the hair is treated with a mild one Shampoo washed and dried.

The shades that can be achieved with the hair colorants according to the invention show an extraordinary result when using different developer and coupler components Variation options that range from yellow to brown, red and blue to purple. The dyeings obtained have good light, wash and rub fastness properties and can easily be removed again with reducing agents.

The following examples are intended to explain the subject matter of the invention in greater detail explain without, however, restricting it to this.

Examples In the following table 1 are in the invention Hair dyes to be used 5-amino-4,6-dioxo-pyrimidine derivatives are listed. The preparation was carried out according to the literature instructions given in the table or analogous to these regulations.

Table 1 Connection no. Compound Literature 1 5-Amino-4,6-dioxo-3,4,5,6- Chem.pharm.Bull. 8, tetrahydropyrimidine 137 (1960) 2 2,5-diamino-4,6-dioxo-3'4,5> 6- Chem.Ber. 26, tetrahydropyrimidine 2551 (1893; 7 3 5-amino-barbituric acid Liebigs Ann. Chem.

127, 223 (1862) 4 5-Amino-1-methyl-barbitur- Chem. Ber. 30, acid 3091 (1897) 5 5-Amino- 1-phenyl-barbituric acid 6 5-Amino-1> 3-dimethyl-barbituric acid Chem. Ber. 27, 3086 säure (1894) The hair dyes according to the invention were in Used in the form of a cream emulsion. This was in an emulsion of 10 parts by weight Fatty alcohols of chain length C12-C18 10 parts by weight fatty alcohol sulfate (sodium salt) Chain length C12-C18 75 parts by weight of water Each 0.01 mol of the in the following Incorporated 5-amino-4,6-dioxopyrimidine derivatives and coupler substances listed in the table. Thereafter, the pH was the Emulsion using ammonia to 9.5 set and the emulsion made up to 100 parts by weight with water.

The oxidative coupling was carried out either with atmospheric oxygen or with 1% hydrogen peroxide solution carried out as an oxidizing agent, with 100 Parts by weight of the emulsion were added to 10 parts by weight of hydrogen peroxide solution. The respective coloring cream with or without the addition of oxidizing agents was closed 90 ffi gray, not specially pretreated human hair applied and there Leave for 30 minutes.

After completing the dyeing process, the hair was treated with a usual Shampoo washed out and then dried. The colorations obtained in this way can be found in Table 2 below.

The following compounds served as coupler components: A C -naphthol B m-diaminoanisole, C 1-phenyl-3-amino-pyrazolone- (5) D resorcinol monomethyl ether.

The developer component numbers in Table 2 correspond the numbers in Table 1.

T: a b e 1 1 e 2 Example of dye components Coloring on hair with no. oxidation by developer coupler atmospheric oxygen 1% H202 solution 1 1 A pastel violet pastel violet 2 1 B olive olive 3 2 A blue purple 4 2 D matt red matt red 5 3 A smoke blue blue gray 6 3 C light yellow matt yellow 7 4 A violet gray violet 8 4 B brown brown 9 5 A gray-violet gray-violet 10 5 D brown-orange orange-brown 11 5 B olive brown olive brown 12 6 A delft blue smoke blue 13 6 C golden yellow golden yellow 14 6 D brown orange brown orange 15 6 B olive olive 16 4 C yellow deep yellow The above It can be seen from the table that the color develops with atmospheric oxygen can take place and to an extraordinary variety of color tones leads, which are characterized by good light, wash and rub fastness properties and can be easily removed again with reducing agents.

Claims (4)

Claims 1) Hair dyes based on oxidation dyes, characterized by a content of 5-amino-4,6-dioxo-pyrimidine derivatives of the general formula in which R is a hydrogen atom or the radical -N R3R4 and R1 - R4 can represent a hydrogen atom, an alkyl radical with 1 - 4 carbon atoms, a hydroxyalkyl radical with 1 - 4 carbon atoms, a phenyl radical, substituted phenyl radical or aralkyl radical, furthermore R3 and Rg with the Nitrogen atom to form a 5- or 6-membered heterocyclic ring, which may contain a further nitrogen atom or oxygen atom, can be closed, as well as their inorganic or organic salts as developer substances and the coupler substances customary in oxidation hair dyes. 2) hair dye according to claim 1, characterized by a content on a mixture of the 5-amino-4,6-dioxopyrimidine derivatives as a developer component with the coupler substances common in oxidation hair dyes. 3) Hair dye according to claim 1 and 2, characterized by a Content of other customary developer substances and, if appropriate, customary substantive substances Dyes. 4) Hair dye according to claim 1 - 3, characterized by a Content of developer-cup 1 combinations of 5-amino-4,6-dioxo-pyrimidine derivatives and coupler substances commonly used in hair coloring from 0.2 to 5 percent by weight, preferably 1 to 3 percent by weight.