DE2523629A1 - Hair dyeing agents based on oxidation dyes - contain 5,6-diamino 4-oxo pyrimidine cpds. as developing agents - Google Patents

Abstract

Hair dyeing agents based on oxidn. dyes contain 5,6-diamino-4-oxo-pyrimidine derivs. of formula: in which R1-R4 = H, 1-4C alkyl, 1-4C hydroxyalkyl, phenyl, substd. phenyl or aralkyl gp., or R1 and R2 together with the N atom form a heterocyclic 5- or 6-ring which opt. contains a further N or O atom; X = O or S, and their (in)organic salts, as developing agents together with couplers normally used in oxidn. hair dyes. (I) are toxicologically and dermatologically more acceptable than prior art couplers such as m-phenylenediamine derivs., phenols, naphthols, resorcinol derivs. and pyrazolones, and gives the desired colour tones in sufficient intensity with good affinity to human hair.

Description

"Hair dye" The invention relates to oxidative agents Coloring of hair based on 5,6-diamino-4-oxo-pyrimidinder ivaten as a development chatter 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 Fulfill the requirements: You mass in 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 compound class commonly used as developer subsets the substituted bzl; s. unsubstituted p-phenylenediamines has the disadvantage that they at one Range of people sensitizations and in their Wake causing severe allergies. Another disadvantage is that they are difficult to remove again. The most important to avoid this dermatological Disadvantages of recently proposed developer substances can be in their application technology 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 5,6-diaminot-oxo-pyrimidine derivatives of the general formula in which R1 - R1p can independently represent hydrogen, 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 R1 and R2 with the nitrogen atom to form a 5- or 6-membered group hecerocyclic ring, which can contain a further nitrogen atom or oxygen atom, can be closed, X denotes an oxygen atom or sulfur atom, as well as their inorganic or organic salts as developing substances and the coupling substances common in oxidative hair dyes meet the requirements set 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. In addition the 5,6-diamino-4-oxo-pyrimidine derivatives according to the invention are characterized by very good fastness properties of the dyeings obtained therewith, due to good solubility in water, good storage stability and toxicological and dermatological harmlessness the end.

The 5,6-diamino-4-oxo-pyrimidine derivatives to be used according to the invention as developer components can either as such or in the form of their salts with inorganic or organic Acids such 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 5,6-diamino-4-oxo-pyrimidine derivatives are already known from the literature. You can click on the take place in a wide variety of ways, as indicated in the examples given in dssr References is described in more detail.

Developer components to be used according to the invention are e.g. 5,6-diamino-uracil, 5,6-diamino-2-thio-uracil, 5,6-diamino-3-methyl-uracil, 5,6-diamino-3-methyl-2-thio-uracil, 5-amino-6-methylamino-3-methyl-uracil, 5-amino-6-methylamino-3-methyl-2-thio-uracil, 5-Amino-6-hydroxyäthylamino-3-methyl-uracil, 5-Amino-6-hydroxyäthylamino-3-methyl-2-thio-uracil, 5-amino-6-benzylamino 3-methyl-uracil, 5-amino-6-benzylamino-3-methyl-2-thiouracil, 5-amino-6-anilino-3-methyl-uracil, 5-amino-6-anilino-3-methyl-2-thio-uracil, 5,6-diamino-1-phenyluracil, 5,6-diamino-1-phenyl-2-thio-uracil, 5,6-diamino-1,3-dimethyl-uracil, 5,6-diamino-1,3-dimethyl-2-thiouracil, 5-Amino-5-methylamino-1, 3-dimethyl-uracil, 5-Amino-6-ethylamino-3-propyl-uracil, 5, 6-diamino-1,3-diisopropyl-uracil, 5,6-diamino-5-butyl-uracil, 5-amino-6-butylamino-1,3-dipropyl-uracil, 5-Amino-6-hydroxyäthylamino-1,3-dimethyl-uracil, 5-Amino-6-benzylamino-1,5-dimethyl-uracil, 5-amino-6-anilino-1,3-dimethyl-uracil, 5-amino-6-dimethylamino-1,3-dimethyl-uracil, 5-amino-6-diisopropylamino-1, -dimethyluracil, 5-amino-6-anisidino-1,5-dimethyl-uracil, 5-amino-6-piperidino-3-methyl-uracil, 5-amino-6-morpholino-1,3-dimethyl-uracil, 5-amino-6-morpholino-1,3-dimethyl-2-thio-uracil, 5-amino-6-piperidinol, 5-dimethyl-2-thio-uracil to call.

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

The developer components are used in the hair dyes according to the invention generally roughly molar Quantities based on those used Coupler substances, used. Even if the molar use proves to be expedient proves, so it is not disadvantageous if the developer component in a certain excess or deficit 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 5,6-diamino-4-oxo-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 any customary substantive components Contain dyes in the mixture, if this is necessary to achieve certain color nuances is.

The oxidative coupling, i.e. 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 nitrate as well as mixtures of such hydrogen peroxide systems, erungsverbindungen with potassium peroxide disulfate into consideration.

The drainage components according to the invention have 5,6-diamino-4-oxo-pyrimidine derivatives have the advantage that they are already oxidative Coupling by atmospheric oxygen deliver fully satisfactory dyeing 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 you want a lightening effect on your hair, you should also use oxidizing agents necessary.

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 in coupler-developer combinations is 0.2 to 5 percent by weight, preferably 1-3 percent by weight.

The dye components are used in the production of creams, emulsions or gels mixed with the other ingredients customary for such preparations. as such additional ingredients are e.g. wetting or emulsifying agents from the anionic or non-ionic type such as alkylbenzenesulfonates, fatty alcohol sulfates, alkylsulfonates, Fatty acid alkanolamides, addition products of ethylene oxide with fatty alcohols, thickeners, such as methyl cellulose, starch, higher fatty alcohols, paraffin oil, fatty acids, and more Perfume oils and hair care products such as pantothenic acid and cholesterol should be mentioned.

The additives mentioned are used in those customary for this purpose Amounts used, such as wetting and emulsifying agents in concentrations of 0.5 - 30 percent by weight and thickener in concentrations of 0.1-25 percent by weight, each 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 medium at at a pH of 8-10. The application temperatures vary in the range from 15 to 40 ° C. After an exposure time of approx. 30 minutes removes the hair dye from the hair to be colored by rinsing. After that it will Washed hair with a mild shampoo 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 blonde to red and blue to purple. The scored Dyeings have good light, wash and rub fastness properties and can be easily peel off 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 Table 1 below, the 5,6-diamino-4-oxo-pyrimidine derivatives to be used for hair dyes 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. R1 R2 R3 R4 X Manufacture according to literature 1 HHHHO J. Amer. Chem. Soc. 55, 1667 (1933) 2 HHHHS Liebigs Ann. Chem. 331, 64 (1904) 3 HH CH3 HO Chem. Ber. 90, 2272 (1957) 4 CH3 H CH3 HO Chem. Ber. 98, 1060 (1965) 5 CzH OH H CH3 HO - 6 C6H5CH2 H CH3 H 0 Chem. Ber. 95, 1597 (1962) 7 C6H5 H CH3 HO - 8 HHH C6H5 O - 9 HH CH3 CH3 O Chem. 3er. 88, 1306 (1955) 10 CH3 H CH3 CH3 O Liebigs Ann. Chem. 612, 158 (1958) 11 C2H4OH H CH3 CH3 O - 12 C6E5CH2 H CH3 CH3 O - 13 C6H5 H CH3 CH3 O - 14 OH3 CH3 CH3 CH3 O Chem. Ber. 104, 780 (1971) The hair colorants according to the invention were used in the form of a cream emulsion. In this case, in an emulsion of 10 parts by weight of fatty alcohols of chain length C12-C18, 10 parts by weight of fatty alcohol sulfate (sodium salt) chain length C12-C18, 75 parts by weight of water in each case 0.01 mol of the 5, 6 listed in the table below -Diamino-4-oxo-pyrimidine derivatives and coupler substances incorporated. The pH of the emulsion was then adjusted to 9.5 using ammonia and the emulsion was made up to 100 parts by weight with water.

The oxidative coupling was carried out either with air or with 1 point hydrogen peroxide solution carried out as the 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 ß gray, not specially treated human hair applied and there Leave for 30 minutes. After completing the dyeing process, the hair was finished with a Washed out conventional shampoos and then dried. The received The colorations are shown in Table 2 below.

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

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

Table 2 Example of dye components from dyeing on hair No developer coupler oxidation by atmospheric oxygen goat H202 solution 1 1 B violet dark purple 2 1 A purple gray purple gray 3 1 C brown orange terra di Siena 4 1 D brown nougat-colored 5 2 A blue-gray gray-purple 6 2 B blue violet 7 2 C old pink orange 8 3 B violet brown dark ruby 9 3 C copper red brick red 10 3 D brown orange brown orange 11 4 A sulfur blue sulfur blue 12 4 B olive olive 13 5 A. solid violet dark violet 14 5 B blue gray blue 15 6 C brown orange brown orange 16 7 C violet brown violet brown 17 8 A blue blue 18 9 A purple magenta 19 9 B ruby magenta 20 10 C brown orange brown orange 21 10 B olive olive brown 22 12 A gray blue gray blue 23 12 C orange red light red 24 13 B brown orange brown 25 14 C blond blond 26 14 B olive olive brown The above It can be seen from the table that the color develops with atmospheric oxygen can be done and to an extraordinary possibility of variation leads to color shades, which are characterized by good light, wash and rub fastness properties and can be easily removed with reducing agents.

Claims (4)

Claims ) Hair dyes based on oxidation dyes, characterized by a content of 5,6-diamino-4-oxo-pyrimidine derivatives of the general formula in which R1-R4 independently of one another can represent hydrogen, a ^ Sf t 1 - 4 carbon atoms, a hydroxyalkyl radical with 1 - 4 carbon atoms, a phenyl radical, substituted phenyl radical or aralkyl radical, furthermore R1 and R2 with the nitrogen atom to a 5- or 6- membered heterocyclic ring, which can contain a further nitrogen atom or oxygen atom, can be closed, X denotes an oxygen atom or sulfur atom and 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 5,6-diamino-4-oxopyrimidine 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 common developer substances and, where appropriate, common direct-acting substances Dyes. 4) hair colorant according to claim 1 - 3, characterized by a Content of developer-coupler combinations of 5,6-diamino-4-oxo-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.