DD297325A5 - EGALIZING OXIDATION HAIR AGENT - Google Patents

Abstract

The levelling action of oxidative hair dyes containing as the oxidative dye 2,4,5,6-tetraaminopyrimidine, or a derivative thereof, can be improved by the addition of histidine or its salts. Particularly intense and uniform dyeing of the hair is obtained if, in addition to 0.1-10 % by wt. of histidine, the hair dye contains 0.1-5 % by wt. of N-2-hydroxyethylacetamide.

Description

NR ⁵ R ⁶

in the R ¹ to R ⁶ independently of one another hydrogen, alkyl groups having 1-4 C atoms or hydroxyalkyl groups having 2-4 C atoms or the groups R ¹ and R ² or R ³ and R ⁴ or R ⁵ and R ⁶ in each case together with the nitrogen atom form a morpholine, piperidine, pyrrolidione or piperazine ring, or salts thereof and as coupler components one or more compounds from the group resorcinol, 2-methylresorcinol, 2,7-dihydroxynaphthalene, 2,6-dihydroxy-3 , 4 dimethylpyridine or salts thereof.

The invention relates to oxidation hair colorants containing as a developer component a 2,4,5,6-tetraaminopyrimidine and as an aid for improving the uniformity of hair coloring histidine or a water-soluble salt thereof. For the dyeing of hair, the so-called oxidation colors, which are formed by oxidative development of oxidation dye precursors play a preferred role. Oxidative hair dyes contain such oxidation dye precursors together with coloring aids in a cosmetic carrier. As oxidation dye precursors so-called developers or oxidation bases are used which form the dyes either with each other or with so-called couplers (color modifier) under the influence of oxidizing agents. As developers, primary aromatic amines are usually used with another in para or ortho position, free or substituted amino or hydroxy group and diaminopyridines, heterocyclic hydrazone derivatives, 4-aminopyrazolone and tetraaminopyrimidines. As so-called coupler substances, m-phenylenediamines, m-aminophenols, resorcinols, naphthols and pyrazolones are used.

As Därbehilfsmittel z. As antioxidants to prevent premature oxidation, pH adjuster, buffering agents and hair cosmetic additives used. Suitable carriers are for. As creams, emulsions, gels or foaming solutions, shampoos, aerosols or other preparations that are suitable for use on the hair. A particularly valuable developer component, which forms a wide range of intense color shades with good fastness properties with many known couplers, is 2,4,5,6-tetraaminopyrimidine and its derivatives. Many of the achievable with 2,4,5,6-tetraaminopyrimidine hair dyes have the disadvantage that they attract unevenly on the hair and z. B. stain the more stressed hair tips much more intense than the less damaged areas of the hairline.

It has now been found that the uniformity of hair coloring with oxidation hair colorants containing as developer component 2,4,5,6-tetraaminopyrimidine or its derivatives can be substantially improved by the addition of histidine or a water-soluble salt thereof.

The histidine may be in free form or as a salt, e.g. B. as carbonate, hydrochloride, sulfate, phosphate, acetate, propionate, lactate or citrate. In order to achieve marked leveling, it is sufficient to add the histidine or its salts in an amount of 0.1-10% by weight, preferably 1-5% by weight, calculated as free histidine, to the colorant. (All data in% by weight relate to the proportion based on the oxidation hair dye according to the invention before the addition of an oxidizing agent.)

As a further, the color depth and leveling the coloring improving aid, the N- (2-hydroxyethyl) acetamide has been found, its beneficial effect on the intensity and fastness of hair dyes already known from DE 2942376C2. In combination with the histidine, however, results in a disproportionate, d. H. synergistic increase in color depth and levelness of coloring. The 2-hydroxyethyl-acetamide is preferably used in an amount of 0.1-5 wt .-% in the Oxidationshaarstärbemittel. The suitable developer component 2,4,5,6-tetraaminopyrimidine is z. B. from DE 23593P9 known. However, its derivatives of general formula I are also suitable

NR ³ R ⁴

NH ₂

in the R 'to R ^e independently of one another hydrogen, alkyl groups having 1-4 C atoms or hydroxyalkyl groups having 2-4 C atoms or the groups R ¹ and R ² or R ³ and R ⁴ or R ⁵ and R ⁸ in each case together with the nitrogen atom form a morpholine, piperidine, pyrrolidine or piperazine ring, or their salts with inorganic or organic acids, for. Example in the form of hydrochlorides, sulfates, phosphates, acetates, propionates, lactates or citrates.

As a coupler, virtually all known coupler compounds which form useful colors with tetraaminopyrimidine are suitable. However, preferred couplers for the oxidation hair dye according to the invention are resorcinol, methylresorcinol, 2,7-dihydroxynaphthalene, 2,6-dihydroxy-3,4-dimethylpyridine and their salts.

In addition to 2,4,5,6-tetraaminopyrimidine and its derivatives of the formula I, the hair colorants according to the invention may contain other known developer substances which are necessary for modifying the color shades and for producing natural-looking shades, for example. As p-phenylenediamine, p-aminophenol, o-aminophenol or derivatives thereof. Given '.falls also direct dyes can be used in addition to the nuance. Such direct dyes are z. As nitrophenylenediamines, nitroaminophenols, nitrophenols, anthraquinone or indophenols. Developer and coupler substances are generally used in approximately molar amounts, but it is not disadvantageous if individual oxidation dye precursors are present in excess, so that developer substances and coupler substances may be present in a molar ratio of 1: 0.5 to 1: 2. 2,4,5,6-Tetraaminopyrimidine and its derivatives are contained in the hair dyes according to the invention preferably in amounts of 0.1 to 10 millimoles per 100 g of the hair dye. In addition to the leveling agents mentioned, histidine and N- (2-hydroxyethyl) acetamide, the oxidation hair colorants according to the invention may also contain further dyeing auxiliaries. Among these are:

- Antioxidants, ζ. Br sodium sulphite, ascorbic acid,

- alkalizing agent, ζ. As ammonia, alkanolamines such as mono-, di- and triethanolamine, isopropanolamine, basic amino acids such. B. ornithine and arginine,

- Buffer substances, for. Ammonium carbonate, ammonium chloride, ammonium sulfate,

- complexing agent, e.g. i-hydroxyethane-i.i-diphosphonic acid, nitrilotriacetic acid, ethylenediaminetetraacetic acid,

- Hair cosmetic aids, eg. B. water-soluble, cationic polymers, glucose, D-panthenol, protein derivatives, cholesterol,

- solubilizers, e.g. Isopropanol, 1,2-propylene glycol, glycerol,

direct hair dyes, e.g. Nitrophenylenediamines, nitroaminophenols and anthraquinone dyes.

To prepare the oxidation hair dye according to the invention, the oxidation dye precursors and the dyeing auxiliaries are incorporated into a suitable cosmetic carrier. Preferred carriers are gels and cream emulsions. Typical constituents of such carriers are, in addition to water, soaps, in particular ammonium oleate, nonionic, amphylotic and anionic wetting and emulsifying agents, eg. Fatty alcohol sulfates, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alpha-olefin sulfonates, ethylene oxide addition products to fatty alcohols, fatty acids, alkylphenols, glycerol and sorbitan fatty acid partial esters, fatty acid alkanolamides and fatty components, eg fatty alcohols containing 12-22 C-atoms, paraffin oils or fatty acid esters, water-soluble thickeners , ζ. As methyl or hydroxyethyl cellulose, starch, carboxymethyl cellulose, guar, vegetable gums and synthetic, water-soluble polymers with thickening effect and perfume oils. In a particularly preferred embodiment, the hair dye according to the invention is a cream emulsion containing 0.1-25% by weight of a fat component, 0.5-30% by weight of an emulsifier from the group of anionic, nonionic, zwitterionic or ampholytic surfactants, contains 0.1-10 millimoles per 100 g of developer components and coupler components, as well as conventional dyeing auxiliaries. The histidine is contained therein in an amount of 0.1-10 wt%. The oxidative development of the dyeing can in principle be carried out with atmospheric oxygen. Preferably, however, a chemical oxidizing agent is added shortly before use, especially if, apart from the coloring, a lightening effect on the hair is desired. Suitable oxidizing agents are, in particular, hydrogen peroxide or its addition products of urea, melamine or sodium borate and mixtures of such hydrogen peroxide addition products. The application of the hair dye according to the invention, regardless of the type of cosmetic preparation, for. B. as a cream, gel or shampoo, preferably in a pH range of 6-10. Especially preferred is di <? Application of hair dye in a weak alkaline environment. The application temperatures can range between 15 ⁰ C and 40 ° C. After a contact time of about 30 minutes, the hair dye by rinsing of the zu

removing coloring hair. Thereafter, the hair is washed with a mild shampoo and dried. The washing with a shampoo is eliminated if a strong surfactant-containing carrier, eg. As a dyeing shampoo was used.

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

Examples

Hair colorants according to the invention were prepared in the form of a hair dye cream emulsion. Hair strands that were untreated in the lower part, were previously defined in the upper part, stained with it and measured the color differences between damaged and undamaged hair regions and evaluated mathematically.

1. Preparation of hair dye cream emulsion

The hair dye cream emulsions were prepared according to the compositions given in Table 1 as follows: The fatty alcohols were melted and emulsified with the fatty alcohol ether sulfate and 30 g of water at 90 ° C. The emulsion was cooled to 60 ^° C. Then ascorbic acid and histidine were added dissolved in 20 g of water at 90 ° C. The oxidation dye precursors were then dissolved in 10 g of water at 90 ° C., adjusted to pH = 9.5 with concentrated ammonia and added. After cooling to 3O ⁰ C, the remaining components were added in the order given and the emulsions with concentrated ammonia solution adjusted to pH = 9.5 and supplemented with water to 100g and homogenized.

For comparison, the formulations were also prepared without histidine (instead, an appropriate amount of water was added).

2. Hair coloring

The oxidative development of the dyeing was carried out with 6% hydrogen peroxide solution as the oxidizing agent. For this purpose, 100 g of the emulsion with 50 g of hydrogen peroxide solution (5%) were added and mixed. The ready-to-use dye preparations were then applied to approximately 15 cm long and approximately 2 g thick hair strands, which were pretreated in the following manner:

The upper half of the hair tress (the tip of the hair tip) was treated for 30 minutes with the aqueous solution of an ammonium thioglycolate based cryogenic agent. After fixation (10 minutes, potassium bromate solution), the same half of the hair strands were ultra-bleached with an aqueous solution of hydrogen peroxide and ammonium peroxide disulfate. This was followed by another treatment with the cold corrosive, the fixation and the Ultrablondierung. The lower half of the strand of hair (root area) was ultra-blonded only once. In this way, two differently stressed hair strands halves were obtained.

The coloring creams were then left for about 30 minutes at 27 ⁰ C on the strands of hair, then washed with water. After rinsing with water, the highlights were then dried.

3. Determination of the Uniformity of the Hair Preparation by Measurement of the Color Distance Values (DE Values)

Each strand of hair was measured at eight points (four in the area of the hairline and four in the area of the hair tip) using a color measuring system from Datacolor. The specimen to be measured was fixed to the spectrophotometer in a clamping device and the reflectance values were measured over the visible light range of 390-700 nm at a distance of 10 nm and processed by a computer (minicomputer HP 2113E). The computer program determines the standard color values according to the CIE system (Commission Internationale de l'Eclairage) in accordance with DIN 5033 and converts them into color space numbers according to DIN 6174.

In the practice of hair coloring with oxidation hair dyes, DE values below 12 can be considered satisfactory and acceptable if there is no visible hue difference.

The hair tresses stained with the hair colorants of Examples 1-5 according to the invention did not show a color tone difference discernible to the naked eye between the more damaged upper half and the less damaged lower area of the hair. The visible differences only affect the intensity or color intensity.

Table 1

Composition in g / 100 g 12 3 4 5

Hydr. Tallow fatty alcohol C _{ie /} | ₈ Coconut oil fatty alcohol C, _{2 /} , 8 fatty alcohol C, 2 / H + 2 EO sulfate

Na salt, 28% aqueous solution 25.0 25.0 25.0 25.0 25.0

Water 30.0 30.0 30.0 30.0 30.0

6.5 6.5 6.5 6.5 6.5 2.0 2.0 2.0 2.0 2.0

histidine 5.0 1.0 1.0 1.0 1.0 ascorbic acid 0.4 0.4 0.4 0.4 0.4 water 20.0 20.0 20.0 20.0 20.0 2,4,5,6-tetra 2,082 2,082 2,082 2,082 2,082 resorcinol - - - 0,220 0,220 2-methyl 0.993 0,496 0,496 - - 2,7-dihydroxy-3,4-dimethyl-pyridine - 0.492 0.492 0,740 0,740

Table 1 (continued)

Composition in g / 100 g 12 3 4 5

(NH ₄ I ₂ CO ₃ Na ₂ SO ₃

2-hydroxyethylacetamide

1.0 1.0 1.0 1.0 1.0 0.5 0.5 0.5 0.5 0.5 - - 0.5 - 0.5

to pH = 9.5

conc. Ammonia solution water mahagony coral red ad 100g henna gold henna gold Färbenuancen 4.48 10.77 coral red 10.88 7.22 DE value (color difference) 20.01 27.23 8.56 25.56 25.56 Comparison DE value without histidine 27.23

Claims (5)

1. oxidation hair colorant containing oxidation dye precursors and dyeing aids in a cosmetic carrier, wherein at least one 2,4,5,6-tetraaminopyrimidine or a derivative thereof or its water-soluble salts are contained as the developer component, characterized in that as leveling agent histidine or a water-soluble salt thereof is included. 2. oxidation hair dye according to claim 1, characterized in that N- (2-hydroxyethyl) acetamide is included as a further dyeing assistant. 3. oxidation hair colorant according to claim 1, characterized in that histidine or its salts in an amount of 0.1-10 wt .-%, calculated as free histidine are included. 4. oxidation hair dye according to claim 2, characterized in that N- (2-hydroxyethyl) acetamide is contained in an amount of 0.1-5Gew .-%. 5. oxidation hair dye according to claim 1 or 2, characterized in that 2,4,5,6-tetraaminopyrimidine or its derivatives of the formula NR ³ R ⁴