DE2359399C3 - Hair dye - Google Patents

Description

in

20th

is, in which Ri-R _{6 is} hydrogen, an alkyl radical with 1 -4 carbon atoms,

the radical - (CH ₂ J _n -X, in which n = 1-4 and X are a hydroxyl group, a halogen atom, an _NHr, -NHR'- and -NR'R "group, where R 'and R" are alkyl radicals with 1-4 carbon atoms or are closed with the nitrogen atom to form a heterocyclic ring which can contain another nitrogen atom or oxygen atom,

an optionally substituted aryl radical an optionally substituted heterocyclic 5- or 6-membered ring with one or two nitrogen atoms or one nitrogen atom and represent an oxygen atom, wherein the tetraaminopyrimidine can also be present as an inorganic or organic salt.

2. Hair dye according to Claim 1, characterized in that it additionally contains customary developer components and, if appropriate, customary substantive dyes

3. Hair dye according to claim 1 and 2, characterized in that it is a developer-coupler combination of tetraaminopyrimidine and Coupler component customary in hair coloring 0.2 to 5 percent by weight, preferably 1 to 3 Weight percent, contains.

4. Hair dye according to claim I, characterized in that Ri and R * R3 and fU or R5 and R _{6 are joined together} with the respective nitrogen atom to form an optionally substituted heterocyclic 5- or 6-membered ring with one or two nitrogen atoms or one nitrogen atom and one oxygen atom .

25th

35 4-Amino-pyrazolone derivatives, heterocyclic hydrazones used. As so-called coupler components m-phenylene-diamine derivatives, phenols, naphthols, resorcinol derivatives and pyrazolones are named

Good oxidation hair dye components must first and foremost meet the following requirements;

In the oxidative coupling with the respective developer or coupler components, you have to develop the desired color nuances with sufficient intensity. They must also have a sufficient to very good ability to be absorbed by human hair, and they should also ^{: be} toxicologically and dermatologically harmless.

The compound class of substituted or unsubstituted p-phenylenediamines usually used as developer substances has the disadvantage that it caused sensitization in a number of people and, as a result, severe allergies. The for Avoidance of these dermatological disadvantages recently proposed developer substances cannot always be satisfactory in terms of their application properties.

In the search for useful oxidation hair dyes, the task was therefore to find suitable ones Find components that meet the above requirements in an optimal way.

It has now been found that hair dyes based on oxidation dyes with a content of certain tetraaminopyrimidines meet the requirements to a particularly high degree will. The subject of the invention is therefore a hair dye, consisting of a developer component, a customary coupler component and customary additives, characterized in that the developer component is a tetraaminopyrimidine of the general formula

40

The so-called oxidation colors, which are produced by oxidative coupling, play a role in the coloring of hair Developer components with a coupler component arise because of their intense colors and very good fastness properties play a preferred role. Nitrogen bases such as p-phenylenediamine derivatives, diaminopyridines,

65

R ₄

is, in which Ri - Re is hydrogen, an alkyl radical with 1 -4 Carbon atoms,

the radical - (CH ₂ J _n -X, in which n = 1 -4 and X is a hydroxyl group, a halogen atom, an -NH ₂ -, - NHR 'and - NR'R "group, where R' and R "denotes alkyl radicals with 1-4 carbon atoms or are closed with the nitrogen atom to form a heterocyclic ring which can contain a further nitrogen atom or oxygen atom,

an optionally substituted aryl radical, an optionally substituted heterocyclic radical 5- or 6-membered ring with one or two nitrogen atoms or one nitrogen atom and one Represent oxygen atom, the tetraaminopyrimicline also being inorganic or organic Salt may be present.

When used as developer components, the tetraaminopyrimidines deliver with the in general for

the oxidation hair dyeing used coupler substances the most varied of very intense color nuances, as they were with these couplers and the ones up to now known developers were not achievable and thus represent a significant enrichment of the ί Oxidative hair coloring options. In addition, the tetraaminopyrimidines are very good Fastness properties of the dyeings achieved therewith, due to good solubility in water, good Storage stability and toxicological as well as dermatological ι ο look harmless.

The tetraaminopyrimidines used as developer components can either as such or in Form of their salts with inorganic or organic acids, e.g. as chlorides, sulfates, phosphates, Acetates, propionates, lactates, citrates can be used. The preparation of most of these tetraaminopyrimides is already known from the literature and can Monograph by D. J. Br ο w η, "The Pyrimidines" in the series Heterocyclic Compounds, Interscience Publishers (1962) Volumes I and II. Just a few of the compounds used represent new substances, their production separately is described

The synthesis of the compounds is generally based on 2,4,6-triaminopyrimidines, in which the 5-amino group is introduced by nitrosation and subsequent reduction. But you can also start from appropriately substituted triamino-alkyl mercaptopyrimidines and the alkyl mercapto group jo substitute with amines. The latter method is particularly suitable for introducing amino groups or of substituted amino groups in the 2-, 4- or 6-position of the pyriinidine ring.

The developer components to be used in the hair colorant J5 according to the invention are e.g. B. 2,4,5,6-tetraamino-, 4,5-diamino-2,6-bismethylamino-, 2 _I 5-diamino-4,6-bismethylamino-, 4,5-diamino-6-butylamino-2 -dimethylamino-, 2,5-diamino-4-diethylamino-6-methylamino- ₁ 4,5-diamino-6-diethylamino-2-dimethylamino-, 4,5-diamino-2-diethyIamino-6-methylaniino-, 4,5 -Diamino-2-dimethylamino-6-ethylamino-, 4,5-diamino-2-dimethylamino-6-isopropylamino-, 4 ₁ 5-diamino-2-dimethylamino-6-methylainino- ₁ 4,5-diamino-6- dimethylamino-2-methylamino-, 4,5-diamino-2-dimethyIainino-6-propyIamino-, 2,4,5-triamino-6-dimethylamino-, 4Ä6-triamino-2-dimethylamino-, 2,4 ^ -Triamino-6-methylamino-, 4,5,6-triamino-2-methylamino-, 4,5-diarnino-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 _r 5-triamino-6-benzvlamino-, 2,4,5-triamino-6-benzylidenamino-, 4,5,6-triamino-2-piperidino -,

2,4,6-trismethylamino-5-amino-, 2,4,5-triamino-6-di-n-propylamino, 2.43-triamino-6-morpholino, 2.5 ₁ 6-triamino-4-dimethylamino-, 4,5,6-triamino-2 -morpholino-, 2,4,5-triamino-6 - /? - hydroxyäthylamino-, 4,5,6-triamino-2 - ^ - amino-ethylamino-, 2,5,6-triamino-4 - ^ - methylamino-ethylamino-, 2,5-diamino-4,6-bis -) '- diethylamino-propylamino-,

4,5-diamino-2-methylamino-6- / J-hydroxyethylami no-,

5-amino-2,4,6-triethylamino-,

2,4-bis- / I-hydroxyethylamino-6-anilino-

5-aminopyrimidine to call.

Examples of coupler components to be used in the hair colorants according to the invention are a-naphthol, o-cresol, m-cresol, 2,6-dimethylphenol, 2,5-dimethylphenol, S ^ DimethylphenoI.S ^ -Dimethylphenol, Catechol, pyrogallol, 1,5- or 1,7-dihydroxy-naphthaIin, 5-amino-2-methylphenol, hydroquinone, 2,4-diamino-anisole, m-toluylenediamine, 4-aminophenol, resorcinol, Resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-S-methyl-pyrazolone-S, 1-phenyl-S-aminopyrazolon-S, 1-phenyl ^^ - diketo-pyrazolidine, l-methyl-7-dimethyl-amino-4-hydroxy-quinolone-2, l-Amino-3-acetacety! amino-4-nitro-benzo! or 1-Amino-S-cyanoacetylamino ^ -nitro-benzene to cite.

In the hair dye compositions according to the invention, the developer components are generally approximately molar amounts, based on the coupler substances used, used. If the molar use proves expedient, it is not disadvantageous if the developer component in a certain excess or deficit is used.

Furthermore, it is not necessary that the developer component and the coupler substance be uniform Represent products, rather both the developer component mixtures of the invention Tetraaminopyrimidines to be used as well as the coupler substance mixtures of the above Represent coupler components.

In addition, the inventive Hair dyes other known and customary developer components as well as possibly customary ones contain substantive 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 be carried out by means of atmospheric oxygen, as is the case with other oxidation hair dyes. Appropriately, however, are chemical Oxidizing agents used. In particular, hydrogen peroxide or its addition products with urea, melamine and sodium borate are used as such, and mixtures of such hydrogen peroxide addition compounds with potassium peroxide disulfate in Consideration.

As a developer component, the tetraaminopyrimidines have the advantage that they are already at oxidative coupling by atmospheric oxygen deliver completely satisfactory coloring results and thus hair damage through the otherwise for the oxidative coupling used oxidizing agents can be avoided. However, at the same time in addition to the coloring one If you want a lightening effect on the hair, it is necessary to use oxidizing agents.

The hair colorants according to the invention are used in corresponding cosmetic preparations, such as creams, emulsions, gels or simple ones Solutions incorporated and immediately before the

Use on the hair mixed with one of the oxidizing agents mentioned. Pie concentration of such dyeing preparations of coupler-developer combination is 0.2 to 5 percent by weight, preferably 1 -3 percent by weight. For the production of creams, emulsions or gels, the Dye components mixed with the other ingredients customary for such preparations. as such additional ingredients are e.g. B. network or Anionic or nonionic emulsifier ι ο 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, also perfume oils and hair care products, like pantothenic acid and cholesterol. Pie called additives are used in this the usual amounts used for this purpose, such as. B. wetting and emulsifying agents in concentrations of 0.5-30 weight percent and thickener at concentrations of 0.1-25 weight percent, each based on the entire preparation.

The hair colorants according to the invention can be used, regardless of whether it is a solution, an emulsion, a cream or a gel, in a weakly acidic, neutral or, in particular, alkaline medium at a pH of 8 to 10. The application temperatures are in the range from 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. The hair is then washed with a mild shampoo and dried.

Pie shades that can be achieved with the hair dyes according to the invention show when using different shades Developer and coupler components an extraordinary possibility of variation, that of light blonde until dark brown and green to purple. Pie dyeings have good light, wash and color properties Rubbing fastness properties and can easily be peeled off again with reducing agents.

Examples

First, the preparation of some to be used in the hair dyes according to the invention Tetraaminopyrimidines described, which are not previously known from the literature

Paragraph of

2,4,6-trimethylamino-5-aminopyrimidine sulfate,

C ₇ Hi ₄ N ₆ • H ₂ SO ₄ • 2 H ₂ O

5.5 g of 2,4,6-trismethylaminopyrimidine (prepared according to Winke I ma η η, J. Prakt. Chem., 115,292, [1927]) were dissolved in 50 ml of water and brought to pH 4 with sodium acetate. Pie solution was heated to 80 ⁰ C and a solution of 1.4 g NaNO ₂ in 5 ml H ₂ O added. A red solution resulted. Sodium dithionite was added at 60 ^° C. until the solution was yellow. Dilute H ₂ SO _{4 was} added to the yellow solution and the precipitate was filtered off with suction. Yield 55%.
Mp215 °.

Analysis:

Calculated: C 26.6%, H 6.4%, N 26.6%;
found: C26f%, H 8.3%, N 27.7%.

50 Paration of 2,4,5-triamino-6-di-n-propy | -
aminopyrimidine dihydrochloride, C, oH2oN6 · 2 HCI

2,4,5-triamino-6-di-n-propy! Amino-pyrimidine sulfate
was shown in stages as follows:

1. 2,4-piamino-6-di-n-propylamino-pyrimidine

15 g of 2,4-piamino-6-chloropyrimidine (according to R o th, B _n Smith, J. M _n and Hultquist, E. M _n J. Am. Chem. Soc "72, 1914 [1950]) were prepared in 130 ml of ethanol are mixed with 50 g of pi-n-propylamine and kept in the autoclave at 200 ° C. for 3 hours (initial pressure 10 atm. N ₂ ). After cooling and opening, the reaction mixture was cooled in an ice-saline bath to precipitate Pi-prGpylamine hydrochloride. It was filtered off and the mother liquor was largely concentrated (approx. 20 ml residue), 18 g = 82.9% of the crude product precipitated; this was further processed as such.

2. 2,4-piamino-5-nitΓOSo-6-di-n-propγlaminopyrimidine

18 g of 2,4-piamino-6-di-n-propylamino-pyrimidine (crude product) were slurried in 25 ml of water and glacial acetic acid was added until a pH of 4 was reached; it was then heated to 50 °, the substance being dissolved, and 5.5 g of sodium nitrite in 10 ml of water were slowly added; after a short time a raspberry-red precipitate fell out; suctioned off and dried under vacuum at room temperature, 9.4 g = 46% remained.
M.p .: 206-208 ° C
Analysis:

Calculated: C 50.40%, H 7.61%, N 35.27%;

found: C 49.56%, H 7.62%, N 35.50%.

3. 2,4,5-triamino-6-di-n-propyIaminopyrimidine dihydrochloride

6.5 g of 2,4-piamino-5-nitroso-6-cii-n-piopylaminopyrimidine were hydrogenated in 150 ml of ethanol with 0.5 g of catalyst (10% Fd on charcoal) in a shaking duck at room temperature. After the uptake of _{H 2 had ended} was filtered off from the catalyst, acidified with hydrochloric acid and concentrated.
Residue: 5.6 g = 78.8%, brown crystals, decomp. Point 105 ° C. Pas mass spectrum shows the molecular mass 224 (Ber. 224)

Paragraph of

2,4,5-triamino-6-morpholino-pyrimidine sulfate
C ₈ Hi ₄ N ₆ O • H ₂ SO ₄

2,4,5-Triamino-6-morpholino-pyrimidine-sulfate was prepared in stages from the following compounds:

1. To 10 g of 2,4-piamino-6-chloropyrimidine (according to R o th, B "S mith, JM and H u 11 quist, E. M _n J. Am. Chem. Soc, 72, 1914 [1950] prepared) (0.07 mol), 30 g of morpholine (30 ml 0.34 mol) was added and AjF under stirring within one hour heated 100 ⁰ C; the mixture was kept at this temperature for 2½ hours; then 10 ml of ethanol were added and left to stand in the refrigerator until mcrpholine hydrochloride had precipitated, which was separated off. The filtrate was concentrated in order to obtain the crude product as a semi-oily semi-crystalline residue (5.9 = 43.7%); further processed as a raw product.

2. 2,4-Diamino-6-morpholino-5-nitroso-pyrimidine

5.9 g of 2,4-diamiao-6-morpholino-pyrimidine (0.03 mol) (crude product) were dissolved in 25 ml of water while warming, and acetic acid was added until "> pH 4 was reached; then the solution was increased to 80% ^{Heated to 0} C and slowly added a sodium nitrite solution of 2 g in 5 ml of water; after a short time, the nitroso compound precipitated out as a raspberry-red precipitate; concentration and cooling gave a total of 4.1 g = 60.3% yield.
M.p .: 231-233 ° C

Analysis:

Calculated: C 42.85%, H 5.39%, N 37.48%:
found: C 41.92%, 114.97%, N 38.22%.

3. 2,4,5-Tnamino-6-morphc) linopyrimidi η sulfate

2.5 g of 2,4-diamino-6-morpholino-5-nitroso-pyrimi- j < > din were slurried in 15 ml of water and 2N HCl (5 ml) was added until the substance was justified was resolved; the mixture of substances was then heated to 50 "and slowly became so much sodium di thionite (NaÄO-i) added until the purple r, The solution turned yellow: it was then filtered, cooled and adjusted to pH 2 with sulfuric acid (1: 1) set.

After a short time the pyrimidine precipitated as .Suiiai; it 2.6 g = 76.4% were obtained. w

Analysis (recrystallized):

Calculated: C 31.17%, H 5.23%, N 27.25%;
found: C 29.81%, H 4.98%, N 27.86%.

M.p .: sinters at 230 °; slow decomposition, at 255 ° C ν The other tetraaminopyrimidines used in the following examples are known from the literature, and their preparation takes place in ways as described in the monograph by DJ Brown “The Pyrimidines · in Heterocyclic Compounds, Interscience Publisher! 1962 Volume I and II are shown.

The hair colorants according to the invention were used in the form of a cream emulsion. Thereby ii an emulsion

to Ocw.-parts of fatty alcohols of chain length

Cl2 - C | H

10 parts by weight fatty alcohol sulfate (sodium salt)

Chain length Ci; -Cm
75 parts by weight of water

0.01 mol each of the in the table below; listed Telraaminopyrimidin; · and Kiinnlprcuh stamping incorporated. The pH of the emulsion was then adjusted to 9.5 using ammonia and the ( Emulsion; πι ". Water made up to 100 parts by weight The oxidative coupling was carried out either with atmospheric oxygen or with a 1% aqueous peroxide solution Oxidizing agents carried out, being 100% by weight share of the emulsion 10 parts by weight of hydrogen per oxide solution were given. The respective coloring cream with or o ': ne additional oxidizing agent was aul 90% gray, not specially treated! Human hair applied and there for 30 minutes left. After the end of the dyeing process, the hair was selected with a standard shampoo see and then dried. The colorations obtained are shown in Table 1 below remove.

Tabc rile 1 Coupler Q ^: Retain color tone with 1 "» H _: O _: Hey ! ■ Developers with air oxidation olive game m-phenylenediamine olive dark green 1 2.4.5.6-Tetraaminopyrimidine 2,4-diaminoanisole dark green yellow-brown 2 the same m-tolylenediamine yellow-brown purple brown the same m-aminophenol purple brown grey Red 4th the same Resorcinol strawberry red brown orange the same l-phenyl-3-amino- brown orange 6th the same pyrazolone brown orange l-phenyl-3-methyl- brownish red 7th the same pyrazolone golden brown Resorcinol monomethyl golden brown 8th the same ether yellow-brown ^ -Naphthol yellow-brown havana brown 9 the same 1,5-dihydroxynaphthalene havana brown olive brown 10 the same I.7-dihydroxynaphthalene olive brown yellow-brown 11th the same m-phenylenediamine yellow-brown 12th 4-dimethylamino-2,5,6-triamino- olive yellow pyrimidine 2: 4 diamino anisole olive yellow yellow-brown 13th the same m-tolylenediamine yellow-brown burgundy red 14th the same m-aminophenol burgundy red brownish red 15th the same Resorcinol ty Γ3 U f> ΓΟ ί raspberry red I £ the same l-phenyl-3-amino- raspberry red 17th the same pyrazolone

liirlscl / iing Kniwickler 23 59 399 IO \ Hey with I% H ₂ O ₃ 'j game the same Preserved shade of color olive brown \ 9 18th 2-dimethylamino-4,5,6-lriamino- Coupler with air oxidation dark green 19th pyfimidine olive brown the same m-phenylndianiine dark green dark green 20th the same m-phenylenediamine olive yellow 21 the same dark green dark purple ■ 22nd the same 2: 4 diamino anisole olive yellow red-violet 23 the same m-tolylenediamine gray-violet brick red 24 m-aminophenol red-violet the same Resorcinol brick red gray orange ^ 25th l-phenyl-3-amino- the same pyrazolone (5) lacquer red olive brown 26th the same l-phenyl-3-mcthyi- brass gib Τι pyra / olon (5) hair brown d '.- ^ I- ir-naphthol yellow-brown grey Red 28 3-acetyl;> cctamino- the same l-amino-4-nitrobenzene brown orange elienbein 29 the same l-phenyl-3,5-diketo- ivory 30th the same pyrazolone brown orange gray-green 31 the same o-K resol brown orange gray-green 32 the same m-K resol brownish red gray orange 33 the same 2,5-dimethylphenol brown orange Brown 34 the same 3,4-diniethylphenol brown orange metal gray 35 the same 3,5-dimethylphenol Brown pale 36 the same 1,5-dihydroxynaphthalene chocolate brown golden blonde 37 Pyrogallol red-brown Catechol gray orange the same l-methyl-4-hydroxy- Brown 38 the same 7-dimethylamino golden blonde 39 2-piperidino-4,5,6-triaminopyrimidine quinolone-2 Brown dark green 40 the same 5-amino-2-methylphenol brownish red dark purple 41 the same Hydroquinone dark green gray ruby 42 the same m-phenylenediamine dark purple dark green 43 the same m-aminophenol gray ruby brown orange 44 the same Resorcinol dark green tomato red 45 2: 4 diamino anisole brown orange 2-morpholino-4,5,6-triamino- m-tolylenediamine tomato red olive 46 pyrimidine l-phenyl-3-amino- the same pyrazolone (5) olive dark purple 47 the same m-phenylenediamine gray ruby 48 the same dark purple dark green 49 the same m-aminophenol gray ruby olive brown 50 the same Resorcinol dark green brownish red 51 2: 4 diamino anisole olive brown 2-methylamino-4,5,6-triamino- m-tolylenediamine brownish red olive 52 pyrimidine l-phenyl-3-amino- the same pyrazolone (5) olive dark purple 53 the same m-phenylenediamine brown purple 54 the same dark purple dark green 55 the same m-aminophenol grey Red yellow 56 the same Resorcinol dark green brownish red 57 2: 4 diamino anisoi yellow m-tolylenediamine brownish red l-phenyl-3-amino- pyrazolone (5)

l'orlsct / uiig

example

developer

Coupler Hiniillner 1 ^; arbton in air oxidation

with 1% 11.0,

58 6-morpholino-2,4,5-irianiino- m-phenylenediamine pyrimidine 59 the same 2,4-diaminoanisole 60 the same m-tolylenediamine 61 de3gl. m-aminophenol 62 • the same. Resorcinol 63 the same l-phenyl-3-amino- pyrazolone-5 64 6-piperidino-2,4,5-triamino | iyrimidine m-phenylenediamine 65 the same 2,4-diaminoanisole 66 the same m-aminophenol 67 the same Rosorcin 68 the same m-tolylenediamine 69 the same l-phenyl-3-amino- pyrazolone-5 70 o-Di-n-propylamino ^^^ - triamino- m-phenylenediamine pyrimidine 71 the same 2,4-diaminoanisole 72 the same m-tolylenediamine 73 the same m-aminophenol 74 the same Resorcinol 75 the same l-phenyl-3-amino- pyrazolone-5 76 2,4,6-TrismethyIamino-5-amino- m-phenylenediamine pyrimidine 77 the same 2,4-diaminoanisole 78 the same m-tolylenediamine 79 the same m-aminophenol 80 the same Resorcinol 81 the same l-phenyl-3-amino- pyrazolone-5

olive brown olive brown gray-green olive golden yellow brass yellow gray ruby grey Red brownish red brownish red dull red ma I trot bamboo yellow grey yellow olive brown olive olive brown bamboo gelh grey Red ivory grey yellow olive brown gem yellow straw yellow honey yellow olive olive green olive honey yellow honey yellow gray ruby gray ruby brownish red brownish red red-brown red-brown oak brown olive olive beaver brown brass yellow olive dark ruby Brown grey Red dull red red-brown light brown

The tests described below were carried out to test the toxicological and dermatological properties of tetraaminopyrimidines. The test substance used was 2-dimethylamino-4,5,6-triaminopyrimidine sulfate, which was compared to p-phenylenediamine and p-tolylenediamine sulfate. The following results were obtained.

55

1. Acute toxicity

The general tolerance tests were carried out on male white mice of the CF / W-68 strain. The average weight of the test animals was 22 g. The test substances were administered once in increasing doses with the gavage. 10 mice were used per dose. The application volume was constant O ^ ccm / 10 g body weight. After the 8-day observation period and after calculating the test results using the method of Lichfield-Wilcoxon (J. Pharm. Exptl. Ther. 96 99-108 [1949]), the following LD values were found. 2-dimethylamino-4,5,6-triamino-

pyrimidine sulfate 555 mg / kg

p-phenylenediamine 87 mg / kg

p-tolylenediamine sulfate 110 mg / kg

Aqua dest was used as the solvent. used.

2. Skin compatibility tests on hairless mice

In groups of 5 animals per preparation, the test substances were applied to the skin of the back in small amounts in 5% aqueous solutions once a day for 14 days. All animals showed no reaction during the application period and at the end of the experiment.

3. Mucosal compatibility tests on rabbit eyes

These tests of local tolerance were carried out in such a way that small amounts of the 5% aqueous test substances were introduced into groups of albino rabbits once in the conjunctival sac of one eye

60

instilled. The reactions of the mucous membranes of the eyes were based on a point scheme by D r a i ζ e (Appraisal of the safety of chemicals in foods, drugs and domestics. Ass. Of Food and Drug Official of the U.S .. pp. 49-52 [1959]) 2.6, 24 and 48 hours after

14th

of the application evaluated. It was found that p-phenylenediamine led to a slight reddening and Exudation of the conjunctiva leads, which is no longer detectable 24 hours after instillation. The two other test substances were tolerated without reaction.

4. Skin (tissue) compatibility tests on white mice after a single intracellular application of various concentrations of the test preparations

This test of the local compatibility according to Barail (l.Soc. Cosmet. Chemists 11,241 [I960]) is based on the intracutaneous application of small amounts of the test substance in increasing concentrations in the Bauclihkin. of the white mice. After 24 hours will be the test animals were killed, the treated skin areas cut out and dried. Assessing the Skin damage occurs according to a point scheme.

taking into account blood flow and other damage to the treated skin. Since pro Preparation and per test concentration a larger group of 10 mice cingcsetz; was let the above test method shows finer differences in terms of local compatibility. The test results are shown in Table 2 attached.

Table 2

Skin (tissue) compatibility test on white mice after intracutaneous application (test according to Barn ill Average values after assessment of 10 test animals per preparation b / w. per concentration

p-phenylenediamine

2-dimethylamino

4,5.6-triamino-

pyrimidine sulfate

p-Tolylenediamine uH'at

Points or degrees
the utterance

Ex. 0.3 0.9 2.7

0.1 0.3 0.9 0.1 0.3 0.9 2.7

Concentrations of
Test substances in%

The test results listed above show that 2-dimethylamino-4,5,6-triarriino-pyrimidine sulfate with regard to general and local compatibility among the developer substances tested behaves best. In addition to these good toxicological and dermatological properties bring in the hair dye according to the invention Tetraarninopyrimidines to be used have the further advantages that the development of the coloration can already be done with atmospheric oxygen and to an extraordinary range of color shades leads, which are characterized by good light, washing and rubbing fastness properties and with reducing agents are easily removable again.

Claims (1)

Patent claims: J, hair dye consisting of a heterocyclic developer component, a common one Coupler component and customary additives, characterized in that the developer component is a tetraaminopyrimidine of the general formula