JPS6117806B2 - - Google Patents

Description

[Detailed Description of the Invention] The subject of Japanese Patent Application No. 135964/1983 (Japanese Patent Publication No. 10325/1983) is based on the general formula [In the formula, _R1 to _R6 are a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a group -( _CH2 )n-X (in the formula, n=1-4 and X are a hydroxyl group, a halogen atom, - NH ₂ −, −NHR′− and −NR′R″−
R′ and R″ can be alkyl radicals having 1 to 4 carbon atoms, or can be closed with a nitrogen atom to form a heterocyclic ring, which is another nitrogen atom or an oxygen atom. can have −
form. ), one or two optionally substituted aryl residues
1 nitrogen atom or 1 nitrogen atom and 1 nitrogen atom
It may also be an optionally substituted heterocyclic 5- or 6-membered ring having two oxygen atoms. ] This is a hair dye based on an oxidative dye containing tetraaminopyrimidine and its inorganic or organic salt and a coupling substance that is usual in oxidative hair dyes. The tetraminopyrimidines used according to the invention as color developer components can be used as such or in the form of salts with inorganic or organic acids, such as chlorides, sulfates, phosphates, acetates, propionates, lactates, citric acids. Can be used as salt. Color developer components that can be used according to the present invention include, for example, 2,4,5,6-tetraamino, 4,
5-diamino-2,6-bismethyl-amino-,
2,5-diamino-4,6-bismethylamino-, 4,5-diamino-6-butylamino-2-
Dimethylamino, 2,5-diamino-4-diethylamino-6-methylamino-, 4,5-diamino-6-diethylamino-2-dimethyl-amino-, 4,5-diamino-2-diethylamino-6
-Methylamino-, 4,5-diamino-2-dimethylamino-6-ethylamino-, 4,5-diamino-2-dimethylamino-6-isopropylamino-, 4,5-diamino-2-dimethylamino- 6-methylamino-, 4,5-diamino-6-
dimethylamino-2-methylamino-, 4,5-
Diamino-2-dimethylamino-6-propylamino-, 2,4,5-triamino-6-dimethylamino-, 4,5,6-triamino-2-dimethylamino-, 2,4,5-triamino-6 -Methylamino-, 4,5,6-triamino-2-methylamino-, 4,5-diamino-2-dimethylamino-6-piperidino-, 4,5-diamino-6
-methylamino-2-piperidino-, 2,4,5
-Triamino-6-piperidino-, 2,4,5-
Triamino-6-anilino-, 2,4,5-triamino-6-pendylamino-, 2,4,5-triamino-6-benzylideneamino-, 4,5,
6-triamino-2-piperidino-,2,4,6
-trismethylamino-5-amino-,2,4,
5-triamino-6-di-n-propylamino-, 2,4,5-triamino-6-morpholino-, 2,5,6-triamino-4-dimethylamino-, 4,5,6-triamino-2 -morpholino-, 2,4,5-triamino-6-β-hydroxyethylamino-, 4,5,6-triamino-2
-β-amino-ethylamino-, 2,5,6-triamino-4-β-methylamino-ethylamino-, 2,5-diamino-4,6-bis-γ-diethylamino-propylamino, 4,5 -diamino-2-methylamino-6-β-hydroxy-ethylamino-, 5-amino-2,4,6-triethylamino-, 2,4-bis-β-hydroxyethylamino-6-anilino-5- Amino-pyrimidine may be mentioned. When used as a developer component, tetraaminopyrimidine together with coupling substances commonly used in oxidative hair dyes provides the widest variety of extremely intense shades. Moreover, the tetraminopyrimidines according to the invention have a good storage stability and are toxicologically and dermatologically safe due to the very good fastness properties of the dyeings obtained thereby, due to their good solubility in water. Excellent at something. Of the various shades, intense yellow, tan and red are of great importance. The compounds normally used as red- and yellow-coupling components did not show any satisfactory results in combination with tetraaminopyrimidines, which are anyway very good and useful as color developer components. Therefore, in combination with tetraaminopyrimidine as color developer, intense yellow, yellow-brown and red shades can be produced which meet all requirements regarding fastness, stability, toxicological and dermatological safety. The challenge is to find corresponding red and yellow coupling components. These issues are related to the combination of tetraaminopyrimidine used as a color developer and the general formula as a coupling component. (In the formula, R is an alkyl group having 1 to 4 carbon atoms, and n means 0 or 1.) This problem was solved by using it in combination with dihydroxypyridine represented by the following formula. According to the invention, the red and yellow coupling components are, for example, 2,3-dihydroxypyridine,
2,4-dihydroxypyridine, 2,5-dihydroxypyridine, 2,6-dihydroxypyridine, 3,4-dihydroxypyridine, 3,5-dihydroxypyridine, 2,3-dihydroxy-4
-Methylpyridine, 2,3-dihydroxy-5-
Methyl-pyridine, 2,3-dihydroxy-6-
Methyl-pyridine, 2,4-dihydroxy-6-
Methyl-pyridine, 2,6-dihydroxy-4-
Methyl-pyridine, 2,4-dihydroxy-6-
Ethyl-pyridine, 2,4-dihydroxy-6-
Propyl-pyridine, 2,4-dihydroxy-6
-1-propyl-pyridine, 2,4-dihydroxy-6-butyl-pyridine, 2,6-dihydroxy-4-ethyl-pyridine, 2,6-dihydroxy-4-propyl-pyridine, 2,6-dihydroxy-4 -Butyl-pyridine, 2,3-dihydroxy-5-propyl-pyridine, 2,3-dihydroxy-6-butyl-pyridine, 3,5-dihydroxy-6-methyl-pyridine, 3,5-dihydroxy-6-propyl - Pyridine. The dihydroxypyridine to be used as the red- and yellow-coupling component according to the invention is a compound known in the literature or a compound that can be prepared by methods known in the literature, and is described in Erwin Klingberg's professional paper " Pyridine and its derivatives” Interscience Publishing,
1962, Part 3. The coupling component in the hair dye according to the present invention is generally used in an approximately equimolar amount to the color developer used. Although it has been found to be advantageous to use equimolar amounts, it is not disadvantageous to use some excess or deficiency of the coupling component. Furthermore, it is not necessary that the developer component and the coupling substance be a single product; rather, the developer component may be a mixture of tetraaminopyrimidines that can be used according to the invention, and it is also possible that the coupling substance is a mixture of the above-mentioned dihydroxypyridines. It may be hot. Moreover, the hair dyes according to the invention can contain, if necessary to obtain such shades, other known and customary developer components and optionally customary direct dyeing dyes. Oxidative coupling, ie development of the dyeing, can in principle also be carried out with atmospheric oxygen, as is the case with other oxidative hair dyes. However, it is preferred to use chemical oxidizing agents. Suitable oxidizing agents include, in particular, hydrogen peroxide or addition products to urea, melamine and sodium borate, as well as mixtures of such hydrogen peroxide addition compounds with potassium peroxide-disulfuric acid. In this case, the tetraaminopyrimidine according to the invention as developer component already provides very satisfactory dyeing results upon oxidative coupling with atmospheric oxygen and thus avoids hair damage caused by the oxidizing agents used for the oxidative coupling in addition. It has the advantage of being able to However, if at the same time other hair lightening effects are desired, it is necessary to use an oxidizing agent. The hair dye according to the invention can be used in a corresponding cosmetic composition,
They are used, for example, in creams, emulsions, gels or just solutions and are treated with one of the oxidizing agents mentioned above before being applied directly to the hair. The concentration of the coupling component-developing component combination in such dye preparations is from 0.2 to 5% by weight, in particular from 1 to 3% by weight. For the production of creams, emulsions or gels, the dye component is mixed with the other ingredients commonly used in such preparations. Such additional components include, for example, anionic or nonionic wetting agents or emulsifiers, such as alkylbenzole sulfonates, fatty alcohol sulfates, alkyl sulfonates, fatty alkanolamides, addition products of fatty alcohols and ethylene oxide, thickening agents, Examples include methylcellulose, starch, higher fatty alcohols, paraffin oil, fatty acids, as well as perfume oils and hair styling agents such as pantothenic acid and cholesterin. The abovementioned additives are then added in the amounts customary for this purpose, for example wetting or emulsifying agents from 0.5 to 30% by weight and thickening agents from 0.1 to 25% by weight, based on the total composition.
used in The hair dye according to the invention, whether as a solution, emulsion, cream or gel, has a pH value of 8 to 10 in a slightly acidic, neutral or especially alkaline medium. applicable. The application temperature varies in the range from 15 to 40°C. about 30
After an action time of minutes, the hair dye is washed off from the hair to be dyed. The hair is then washed with a loose shampoo and dried. The dihydroxypyridine which can be used as a coupling component according to the invention in combination with a tetraminopyrimidine color developer produces a very intense yellow color, which is distinguished by particularly good light fastness, permeability and toxicological safety. Provides a brown to red hue. It is already known to use various dihydroxypyridines as dye precursors for dyeing human hair. If it is a hydroxypyridine without amino groups, blue to violet colors are obtained.
It was therefore unexpected that the dihydroxypyridine which can be used according to the invention is particularly suitable as a particularly advantageous red and yellow coupling substance in combination with tetraaminopyrimidine. The examples below serve to explain in detail the subject matter according to the invention, but are not limited thereto. EXAMPLES The following compounds are used in the examples below as coupling components. Coupling component K1: 2,3-dihydroxypyridine K2: 2,4-dihydroxypyridine K3: 2,4-dihydroxy-6-methyl-pyridine K4: 2,6-dihydroxy-4-methyl-pyridine The following color developing component: The following compounds are used in the examples. Color developing component E1: 2,4,5,6-tetraminopyrimidine E2: 2-dimethylamino-4,5,6-triaminopyrimidine E3: 2-morpholino-4,5,6-triaminopyridine E4: 2 ,4-bis-dimethylamino-5,6-
Diaminopyridine The hair dye according to the invention is used in the form of a cream emulsion. In this case: 10 parts by weight of fatty alcohols with a chain length of C ₁₂ to _{C 18} 75 parts by weight of fatty alcohol sulfates (sodium salts) with a chain length of C ₁₂ to _{C 18} 0.01 mol in each case in the table below in an emulsion consisting of water The mentioned tetraaminopyrimidine and dihydroxypyridine are mixed and used. After adjusting the pH value of the emulsion to 9.5 using ammonia, the emulsion is made up to 100 parts by weight with water. Oxidative coupling is carried out using atmospheric oxygen or a 1% hydrogen peroxide solution as the oxidizing agent. At that time, emulsion 100
Add 10 parts by weight of hydrogen peroxide solution to the parts by weight. The respective dyeing creams with and without additional oxidizing agents are applied to human hair that grays up to 90% and has not undergone any special pretreatment and are left to stand for 30 minutes. After the end of the dyeing process, the hair is washed with a normal hair wash and then dried. The stainings obtained are listed in Table 1 below. 【table】

Claims (1)

[Claims] 1. General formula as a coupling component (In the formula, R is an alkyl group having 1 to 4 carbon atoms,
A hair dye based on an oxidation dye, which contains dihydroxypyridine (n means 0 or 1) and tetraaminopyrimidine as a color developer substance. 2. The hair dye according to claim 1, which contains a mixture of tetraaminopyrimidines as a color developer component. 3. The hair dye according to claim 1 or 2, which contains a mixture of dihydroxypyridines as a coupling component. 4. The hair dye according to any one of claims 1 to 3, which contains other ordinary color developing substances, other ordinary coupling substances, and optionally ordinary direct dyes. 5. The dye according to any one of claims 1 to 4, containing 0.2 to 5% by weight, in particular 1 to 3% by weight, of a color developer-coupling substance combination consisting of tetraaminopyrimidine and dihydroxypyridine. Hair agent.