DE1619612A1 - Process for dyeing keratinous fibers - Google Patents

Description

PA ΐ f- H IANWi! Τξ - ■ - ".

PROF. DR, DR. J. REITSTÖTT ^ R '

DR.-1N3. TUNGSTEN BUNTE;

D- r IIfO Mi) MCHI-N IS. HAYDNhTRA-Ot. *. S -FtKNiSUf .-. Ijri- f-3 iv?; -.-- _

P 16 19 612.6
L * OBEAL company

Munich * December 9, 1969 M / 8212

Method of coloring Keratin fibers

The invention relates to a method for dyeing Keratin fibers, especially human hair, consist in applying an aqueous layer to the hair Solution of at least one dye according to formula

Documents (Art. R §, ^, \ .., / ,. ^ _{b dc8ÄflUörunfliOiiBi} - ^

in which R is CH ₃ or CH ₂ CH ₂ OH, R * is hydrogen or CH ₃ and η is an integer between 1 and 4 inclusive «applies, and after a period of about 15-40 minutes rinses, washes and dries the hair.

To carry out the hair coloring process, the im previously identified dyes are used, which make it possible to achieve darker shades tending towards blue and in a wide pH range of acidic pH values, preferably between 3 and 10, can be used, while physiologically justifiable and not at all cause harmful side effects on the hair or skin.

The nitro dyes to be used according to the invention can be obtained in such a way that, for example, 1-methylamino-2-nitro-4-aminobenzene with a chloroacylamide of the formula Cl (CH ₂ ) CQHH ₂ * in which η denotes 1 to 4, such as, for example, chloroacetamide or β-chloropropionamide , is brought to reaction and in the resulting N-carbamylalkyl compound, such as l-methylamino ^ -nitro- ^ carbamylmethylaminobenzene or 4- (ß-carbamylethylamino) benzene, the amide group is split off by hydrolysis with hydrochloric acid.

009638/1986

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The coloring agent of the new 'hair dye' can be manufactured in various ways. So can it can be obtained in such a way that first through conversion of l-aisino * -2 ~ nitro-4- (N-methyl-N-carbamylalkyl-araino) -benzene, the alkyl radical containing 1-4 carbon atoms can »with: p-toluenesulfochloride the primary amino group blocked. Then the free hydrogen of this amino group "for example by the action of dimethyl sulfate in a basic medium" against the methyl residue replaced. The tosyl radical introduced in the first stage is then concentrated by the action of Splitting off sulfuric acid and finally split off by the action of concentrated sulfuric acid and seMiesslieh by hydrolysis with concentrated hydrochloric acid Cleaved acid amide group.

It can also be obtained by reacting l-amino-2-nitro-4-methylaminobenzene with a chloroacylamide of the formula Cl (CH ₂ ) CONH ₂ , where η means 1 to 4, such as, for example, chloroacetamide or β-chloropropionamide , a carbamylalkyl radical, such as, for example, a carbaraylmethyl or carbamylethyl radical, is introduced into the secondary amino group in the 4-position. The 1-amino-2-nitro-4-CN-ethyl-N-carbamylalkylamino) -benzene obtained is converted into the ß-chloroethyl ester of the ent-

speaking N-carbamylalkyl compound, such as 2-nitro-4- (N-methyl-N-carbamylmethyl- or -N-carbarayl-ethylamino) -phenyl-carbamic acid, implemented »The acid amide group is then split off by hydrolysis with hydrochloric acid and the compound obtained for the purpose of converting the chloroethyl ester group into the ß-oxyethyl group subjected to alkaline hydrolysis. Then will the monochlorohydrate of the desired compound is obtained by acidification with hydrochloric acid.

Example 1"

Prepare an aqueous solution of:

1-methylamino ^ -nitro- ^ (N-methyl-N-carboxymethylamino) benzene chlorohydrate. 0.3 g

with 10 moles of ethylene oxide oxyäthylenierter

Lauryl alcohol i 5 g

Sodium carbonate until a pH value of 3 is reached and topped up with water to ..... 100 g

This coloring solution is applied to golden yellow bleached hair. After 20 minutes of exposure time, the hair will be washed and rinsed. It becomes an ash blonde with a mother-of-pearl effect obtain.

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Example 2:.

Prepare an aqueous solution of:

l-methylamino-Z-nitro- ^ (N-methyl-iN-carboxy-

methylamino) benzene chlorohydrate ..... »...... * .. *. *. 0.6 g Lauryl aramonium sulfate (20%) .................... 5 g Sodium carbonate until a pH value of 5 is reached and fill up with water ...................... 100 g

This coloring solution is applied to light chestnut brown hair. After an exposure time of 40 minutes the hair washed and rinsed. It turns a maroon Preserved with golden beetle-colored reflections.

Example 3;

Prepare an aqueous solution of:

1- (β-Hydroxyethyl-amino) ^ -nitro- ^ (N-methyl-N-carboxymethylamino) -benzene chlorohydrate ........... 0.6 g

1-Hydroxy-2-amino-5-nitrobenzene .................... 0.01 g With 10 moles of ethylene oxide oxyäthylenierter Lauryl alcohol 5 g Sodium carbonate until a pH value of 9 is reached and top up with water ....................... 100 g

This coloring solution is applied to auburn hair that is up to 50 % white. After an exposure time of

009838/1986

The hair is washed and rinsed for 20 minutes. It
a maroon with a violet effect is obtained.

Example 4;

Prepare an aqueous solution of j

1- (ß-Hydroxyethylamino) -2-nitro-4- (N-methyl-N-carboxymethylamino) benzene chlorohydrate ......... 0.5 g

Laurylammoniurasulfate (20%) 5 g

Sodium carbonate until a pH value of 8 is reached
and make up to 100 g with water

This solution is applied to light, natural brown hair.
After an exposure time of 35 minutes, the hair is washed and rinsed. It becomes an ashen-colored light
Preserved chestnut brown.

Example 5:

Prepare an aqueous solution of:

l-methylamino-i-nitro ^ - (N-carboxymethylami.no) -

benzene chlorohydrate 0.8 g

Sodium carbonate until a pH value of 9.5 is reached

Laurylammonium sulfate (20%) 5 g

and fills up with water to 100 g

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This solution is applied to dark blonde hair. After an exposure line: of 30 minutes, the Hair washed and rinsed. A light chestnut brown with a dark purple effect is obtained.

Example 6 * Prepare an aqueous solution of:

l-methylamino-2-nitrc — 4- (N-carboxymethylamino) -benzene-chlorohydrate ............................... 0.8 g

With 10 mol Äthylenojcyd oxyäthylenated Lauryl-

Sodium carbonate: until a pH value of and fills up: with water .......> ....., »...“ -. .. 100 g

This solution is applied to blonde hair. To an exposure time: the hair will be of 40 minutes washed and rinsed. A dark blonde with a mother-of-pearl effect is obtained.

Example 7s . ..-.-_ -'_-_. - - _:. : "_; .. [- ^ i - ^ _- ' _P _ ,,; _.''■■: Prepare an aqueous solution of: ·" toiffs J; ^ ^:

l-Methyiamino-2-Ilitίo-4- (N-methyl-N-carboxymethyl-amino) -benzene-chlorohydrate; *. »» ...; - ■ .- "·. V. ^r 0.14 g 4-nitro-1,3-diaiain6benzol ........... ^ * - »'; ..:, -. «■. 0.02 g

OOS838 / t9 86

Ammonia (20%) until a pH value of v. and make up to 100 g with water

This solution is applied to straw blonde bleached hair. After an exposure time of 15 minutes the hair rinsed, washed «rinsed again and dried» A beige with strong ash-colored pearlescent reflections is obtained.

Example 8?

Prepare an aqueous solution of:

1- (ß-Hydroxyethylaraino) -2-nitro-4- (N-methyl-H-carboxymethylamino) benzene chlorohydrate 0.15 g

4-nitro-II, 3-diaminobenzene 0.02 g

Ammonia (20%) until a pH value of v. and fill up with water, 100 g

This solution is applied to hair that has been bleached from platinum yellow * After an exposure time of 15 minutes the hair rinsed, washed, rinsed again and dried. A warm beige-gold color is obtained.

Example 9t _; V / ■ ■, · _i ...,.; ..-, .. ■:.:.: .. .-. '■ "- ■ - ■■; ■" ■ - " An aqueous solution is prepared fromί

Ί- (ß-Hydroxyethylamino) -2-nitro'-4- {N-methyl -'-- "" ^: N-carboxymethylamino) -benzo1-chlorohydrate, ....... 0.24 g

4-nitro-l, 3-diaminobenzene .. .. , ........ .Vi ....... 0.08 g ammonia (20%) until a pH value of v , 3 and fill up with water .Vi ^:. 100 g

This mixture becomes 100 %. white hair applied. After an exposure time of 25 minutes, the hair is rinsed, washed, rinsed again and dried. An ash-blonde coloration with a violet-colored effect is obtained.

Example 10; . .

Prepare an aqueous solution of:

1-methylamino ^ -nitro ^ - (carboxymethylamine) benzene chlorohydrate .............................. _0.1 g

4-nitro-1,3-diaminobenzene 0.004 g

Acetoquinone Violet Lumiere N 0.03 g

Acetoquinone Yellow Lumiere RZ 0.03 g

Ammonia (20%) until a pH value of v. 3 and fill up with water to .................... 100 g

This solution is applied to 100 % white hairs. After an exposure time of 20 minutes, the hair is rinsed, washed and dried. It will be a very bright one

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Obtained blonde with a slight pearlescent reflex.

Example 11:

Prepare an aqueous solution of:

l-Methylaraino - ^ - nitro-'l- (ß-carboxyethylamino) benzene chlorohydrate . 1 g

Sodium carbonate until a pH value of v is reached. 9

Lauryl ammonium sulfate (20 i6 ig) 5 g

and make up to 100 g with water

This solution is applied to blonde hair. After an exposure time of 15 minutes, the hair is washed and rinsed. A beige-pink color is obtained.

009838/1986

Claims (2)

P a te η t an s ρ r ü sS e 1. A process for dyeing K @ rätinfasem _s, in particular human hair _s, characterized in that an aqueous solution of at least one dye corresponding to the formula is applied to the hair NH-R R * -N- (CH ₂ ) _n -CCX) H in which R is CH ₃ or CH ₂ CH ₂ QH, R ^{e is} hydrogen or CH ₃ and η is an integer between 1 and 4 inclusive, and rinses, washes and dries the hair after a period of about 15-4O minutes. 2. Dyes according to the general formula 009S3S / 1386 'ν - 12 - NH-R R "-N- (CH ₂ J _n -COOH in which R is CH ₃ or CH ₂ CH ₂ OH, R ^{1 is} hydrogen or CH.j and η is an integer between 1 and 4 inclusive. 212 / V. ORIGINAL INSPECTED 009838/1986