DE2717041A1 - Oxidn. dye-based hair-dyeing compsns. yielding brown shades - contain tetra:amino- pyrimidine developer and resorcinol deriv. coupler - Google Patents

Abstract

Oxidn. dye-based hair-dyeing compsns., as described in the parent patent, contain tetraaminopyrimidines (II) as developers. In this addn., the compsns. contain, as couplers for (II), resorcinol derivs. of formula (I) (where X is an aliphatic 1-4C gp. or -NR1R2 in which R1 and R2 are each H or an aliphatic 1-4C gp.) In combination with (II), (I) yield strong, fast, brown shades. The dyes penetrate through hair, are non-toxic and do not irritate the skin. In an example, an oak-brown shade was obtd. on using 2,4-dihydroxypropiophenone as (I) and 2,4,5,6-tetraaminopyrimidine as (II).

Description

Hair dyes

(Addition to patent. ... ... (patent application P 23 59 399.9)) Subject of the main patent. ...,., (Patent application P 23 59 399.9) are hair dyes based on oxidation dyes with a content of tetraaminopyrimidines of the general formula in which R1 ~ R6 is hydrogen, an alkyl radical with 1 - 4 carbon atoms, the radical - (CH2) -X, in which n = 1 - 4 and X is a hydroxyl group, a halogen atom, an -NH2-, NHR'- and -NR 'R "group, where Rl and R" can be alkyl radicals with 1 - 4 carbon atoms or closed with the nitrogen atom to form a heterocyclic ring, which can contain a further nitrogen atom or oxygen atom, R1 and R2, R3 and R4, and R5 and R6 together with the respective nitrogen atom can represent an optionally substituted heterocyclic 5- or 6-membered ring with one or two nitrogen atoms or one nitrogen atom and one oxygen atom, as well as their inorganic or organic salts as developer substances and the coupler substances customary in oxidation hair dyes.

The tetraaminopyrimidines to be used according to the invention as developer components can either as such or in formula of their salts with inorganic or organic Acids, such as chlorides, sulfates, phosphates, acetates, propionates, lactates, Citrates are used.

Developer components to be used according to the invention are e.g. 2,4,5,6-tetraamino, 4,5-diamino-2,6-bismethylamino-, 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-dimethylamino, 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-trianino-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-benzylamino, 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-dimeth «lamino-, 4,5,6-triamino-2-morpholino-, 2,4,5-triamino-6-ß-hydroxyethylamino-, 4,5,6-triamino-2-ß-amino-ethylamino-, 2,5,6-triamino- 4-ß-methylamino-ethylamino-, 2, 5-diamino-4, 6-bis r (-diethyl -amino-propylamino-, 4, 5-diamino-2-methylamino-6-ßhydroxy-ethylamino-, 5-Amino-2,4,6-triethylamino-, 2,4-bis-ß-hydroxyethylamino-6-anilino-5-aminopyrimidine to call.

When used as developer components, the tetraaminopyrimidines provide with the coupler substances generally used for oxidation hair coloring the most varied, very intense colors. They also stand out the tetraaminopyrimidines according to the invention by very good fastness properties the dyeings achieved therewith, due to their good solubility in water, a good one Storage stability and toxicological as well as dermatological safety.

Among the various color nuances comes the intense brown tones great importance too. The usual way used as brown coupler components Compounds showed in combination with the rest as developer components Very useful tetraaminopyrimidines do not give satisfactory results. It was therefore the task to find brown coupler components in combination with the tetraaminopyrimidines as developer substances, intense brown color nuances deliver that meet all requirements in terms of authenticity, stability, toxicological and dermatological safety.

This object was achieved in that, in combination with the tetraaminopyrimidines used as developer substances, resorcinol derivatives of the general formula as coupler components in which X represents an aliphatic radical with 1-4 carbon atoms or the group -N R2, in which R1 and R2, which can be identical or different, represent hydrogen or an aliphatic radical with 1-4 carbon atoms, is used will.

As coupler components according to the invention are 2,4-dihydroxyacetophenone, 2,4-dihydroypropiophenone, 2,4-dihydroxybutyrophenone, 3,5-dihydroxyacetophenone, 3, 5-dihydropropiophenone, 3, 5-dihydroxybenzoic acid amide, 2,4-dihydroxybenzoic acid amide, 2, 1-dihydroxybenzoic acid ethylamide, 2,4-dihydroxybenzoic acid diethylamide, 2,4-dihydroxybenzoic acid propylamide, 2,4-dihydroxybenzoic acid butylamide, 2,4-dihydroxybenzoic acid dibutylamide, 3,5-dihydroxybenzoic acid diethylamide, 3,5-dihydroxybenzoic acid di-isopropylamide, 3,5-dihydroxybeiizoic acid dibutylamide to call.

The resorcinol derivatives to be used according to the invention as brown coupler components are compounds known from the literature or can be prepared by processes known from the literature Links.

The coupler components are used in the hair colorants according to the invention generally in approximately molar amounts, based on the developer substances used, used.

If molar use also proves useful, so it is but not disadvantageous if the Kuperkornpo component in a certain excess or shortfall to use e1an? t.

It is also not necessary that the developer component and the coupler substance represent uniform products, rather both the Developer component Mixtures of the tetraaminopyrimidines to be used according to the invention as well as the coupler substance mixtures of the aforementioned resorcinol derivatives 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. 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, in particular Hydrogen peroxide or its addition products with urea, melamine and sodium borate, as well as mixtures of such hydrogen peroxide addition compounds with potassium peroxide disulfate into consideration.

The tetraaminopyrimidines according to the invention have 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'through the otherwise for the oxidative Coupling used oxidizing agents can be avoided. However, it will be 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 in coupler-developer combinations is 0.2 to 5 percent by weight, preferably 1 to 3 percent by weight. For the production of creams, emulsions or gels are the coloring components with those for such Preparations mixed with other ingredients. As such additional Components are e.g. wetting or emulsifying agents from anionic or nonionic Type, such as alkylbenzenesulfonates, fatty acid alkanolamides, addition products of ethylene oxide in 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 used for purposes, such as wetting and emulsifying agents in concentrations from 0.5 to 30 percent by weight and thickener in concentrations of 0.1 up to 25 percent by weight, each based on the total 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 400C. After an exposure time of about 30 minutes, the hair dye is removed from the hair to be colored by rinsing, then the hair is treated with a mild one Shampoo washed and dried.

The resorcinol derivatives to be used according to the invention as coupler components in combination with the tetraaminopyrimidine developers deliver very intense brown Color nuances, which are characterized by a particularly high lightfastness, color penetration and toxicological safety.

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

Examples The following examples were used as coupler components The following compounds are used: Coupler component: K 1: 2,4-dihydroxypropiophenone K 2: 3,5-dihydroxybenzoic acid amide The developer component was: 2,4,5,6-tetraaminopyrimidine The hair colorants according to the invention were used in the form of a cream emulsion. This was done 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 Water in each case 0.01 triol of the tetraaminopyrimidine listed in the table below and resorcinol derivative incorporated. Thereafter, the pH of the emulsion was measured using Ammonia adjusted to 9.5 and the emulsion made up to 100 parts by weight with water. The oxidative coupling was carried out using 1 pointer hydrogen peroxide solution as the oxidizing agent carried out, with 100 parts by weight of the emulsion 10 parts by weight of hydrogen peroxide solution were given. The respective coloring cream with additional oxidizing agent was Applied to 90-64 gray, not specially pretreated pineapple hair and there 30 minutes left. After finishing the dyeing process the hair was washed out with a conventional shampoo and then dried. The dyeings obtained are shown in Table 1 below.

Table 1 . a) tLitwickler b) Coupler with Preserved Hue Example a) Developer b) Coupler with 1% H2O solution 1 EK 1 oak brown 2 EK 2 gray-brown

Claims (5)

"Hair dyes" (addendum to patent. ... ... (patent application P 23 59 399.9)) Patent claims: 1. Hair dyes based on oxidation dyes as well as additives known for hair dyes with a content of tetraaminopyrimidines as developer substances according to patent (patent application P 23 59 399.9), characterized by a content of resorein derivatives of the general formula in which X is an aliphatic radical with 1-4 carbon atoms or the group -NR 1R2, in which R1 and R2, which can be identical or different, denote hydrogen or an aliphatic radical with 1-4 carbon atoms, as Coupler components. 2. Hair dye according to claim 1, gel: cnnzei.chnet by a content on a mixture of tetraaminopyrimidines as a developer component. 3. Hair dye according to claim 1 and 2, characterized by a Content of a mixture of resorcinol derivatives as a coupler component. 4. Hair dye according to claim 1-3, characterized by a Content of other common developer substances, other common coupler substances, and, if appropriate, customary direct dyes. 5. Hair dye according to claim 1-4, characterized by a Content of developer-coupler combinations of tetraaminopyrimidines and resorcinol derivatives from 0.2 to 5 percent by weight, preferably from 1 to 3 percent by weight.