DE1619615C3 - Hair dye - Google Patents

Description

NO.

NO,

(D

where R ₁ , R ₂ , R ₃ and R _{4 represent} a hydrogen atom, a lower alkyl radical or a radical of the formula

- (CH ₂ ) ,, - N

denotes in which R ₆ and R ₇ denote a hydrogen atom or a lower alkyl radical or belong to a heterocycle, but R ₆ and R _{7 can} not represent a hydrogen atom if the above alkylamino group on which they are attached to the p-position to the nitro -Group located N atom is bonded, η is an integer between 2 and 6 inclusive, one of the radicals R ₁ , R ₂ , R ₃ or R _{4 is} a radical of the formula

- (CHA-N

Solution of at least one substituted nitrophenylenediamine and optionally other hair dyes and usual additives, which is characterized in that the substituted nitrophenylenediamine a compound of the formula

IO

15th

20th

30th

35

45

and R _{5 represents} a hydrogen atom, a lower alkyl radical, a halogen atom or a lower alkoxy radical or a compound of the formula I in which the amino group of the side chain is quaternized.

2. Colorant according to claim 1, characterized in that its pH value is between 4 and 10, preferably between pH 7 and 9.

3. Colorant according to claim 1 or 2, characterized in that the concentration of The dye of claim 1 is between 0.01 and 3%.

4. A method of coloring human hair which comprises applying a hair dye to the Allowing hair to act and then rinsing and drying, characterized in that a dye is used according to one of the preceding claims allowed to act for 5 to 30 minutes.

The invention relates to an agent for coloring human hair, consisting of an aqueous one NO.

where R ₁ , R ₂ , R ₃ and R _{4 represent} a hydrogen atom, a lower alkyl radical or a radical of the formula

- (CH ₂ ) ,, - N

R ₇

denotes in which R ₆ and R ₇ denote a hydrogen atom or a lower alkyl radical or belong to a heterocycle, but R ₆ and R _{7 can} not represent a hydrogen atom if the above alkylamino group on which they are attached to the p-position to the nitro -Group located N atom is bonded, η is an integer between 2 and 6 inclusive, one of the radicals R ₁ , R ₂ , R ₃ or R _{4 is} a radical of the formula

- (CH ₂ ) ,, - N

40 R ₇

and R _{5 represents} a hydrogen atom, a lower alkyl radical, a halogen atom or a lower alkoxy radical or a compound of the formula I in which the amino group of the side chain is quaternized.

This hair dye has a pH between 4 and 10, preferably between 7 and 9, and the dyes claimed are in one concentration between 0.01 and 3%.

In the hair dyeing process according to the invention, the claimed hair dye is allowed to 5 to Soak on hair for 30 minutes, then rinse and dry hair.

Hair dye based on nitrophenylenediamines are already known (see French patent specification 14 08 167). These are known means used as oxidation dyes and need a stabilizing additive for storage.

In contrast, the hair dyes according to the invention represent direct dyes with a good affinity that deliver intense yellow tones.

The series of derivatives derived from nitroparaphenylenediamine gives hues from red to blue; the series of dyes emanating from nitroorthophenylenediamine produces orange shades.

Because nuances on the hair are practically obtained through mixtures of dyes from yellow to blue

it is very important to have hair dyes in the shades of pure yellow or green-yellow.

The invention is therefore based on the object of providing yellow direct dyes with a good affinity for To create human hair.

This object is achieved by the hair colorant described above.

With the coloring agents according to the invention, intense yellow shades are produced on the treated hair, that easily go into the countryside. It should be noted that the dyes of formula I have a good affinity compared to human hair and the hair colorations carried out with it compared to shampoos are particularly resistant and do not stain the scalp; also are the received The coloration is very permanent.

The colorants mentioned are aqueous solutions of the dyes of the formula I. They do not require any Oxidizing agent to develop the color. Various additives used in hair coloring, such as about organic solvents, thickeners, detergents, perfumes, varnishes and the like Colorants can be added.

The application temperature of the colorants can be varied, preferably it is room temperature.

To adjust its pH value one can use either ammonia or an organic alkali Base, e.g. B. an alkylamine, an alkanolamine or a heterocyclic amine, use.

Mixtures of the dyes of the formula I can also be used and they can also be used as a mixture with other dyes, such as nitro dyes, azo dyes, anthraquinone dyes, or other types use of hair dyes.

example 1

40

Make the following mixture:

1-methyl-2-amino-4 ->'- dimethylamino-propylamino-5-nitro-benzene 0.2 g
Ethoxylated lauryl alcohol

with 10.5 moles of ethylene oxide 4.0 g

Make up to 100 ml with water

This mixture has a pH of 9. It is applied to 100% white hair for 10 minutes at room temperature brought to action. The hair is then rinsed and shampooed washed. A yellow color is obtained.

Example 2

Make the following mixture:

Methyl-y- [N- (2-nitro-4-methyl-5-amino) -phenyl] aminopropyl-

trimothylammonium sulfate 1.9 g

Ethoxylated lauryl alcohol

with 10.5 moles of ethylene oxide 5.0 g

2-n solution (CO ₃ Na ₂ ) up to pH 10
Make up to 100 ml with water

This mixture is applied to 100% white hair for 10 minutes at room temperature brought. The hair is then rinsed and washed with a shampoo; you get a yellow one Color that is stronger than according to Example 1.

55

60 Example 3
Make the following mixture:

l-methyl-2-amino-4-) 3-amino-

ethylamino-5-nitrobenzene 0.25 g

Ethoxylated lauryl alcohol

with 10.5 moles of ethylene oxide 5.0 g

Make up to 100 ml with water

This mixture is applied to 100% white hair for minutes. After Rinsing and washing with shampoo gives a very strong greenish yellow.

B is ρ ie 1 4
Make the following mixture:

l-methyl-2-amino-4-ß-amino-

ethylamino-5-nitrobenzene 0.042 g

l-N- / S-aminoethylamino-2-nitro-4-N'-di- / I-hydroxy-ethylamino-

benzene dichlorohydrate 0.252 g

Ethoxylated lauryl alcohol

with 10.5 moles of ethylene oxide 4.0 g

2-n solution (CO ₃ Na ₂ ) up to pH 9 Make up to 100 ml with water

This mixture is applied to 100% white hair for 10 minutes. After Rinsing and washing with shampoo gives a maroon.

Example 5

Make the following mixture:

1-methyl ^ -amino ^ -y-dimethylaminopropylamino-5-nitrobenzene ... 0.025 g l-N-ß-aminoethylamino-2-nitro-4-N'-di- | S-hydroxy-ethylamino-

benzene dichlorohydrate 0.288 g

Ethoxylated lauryl alcohol

with 10.5 mol of ethylene oxide 4 g

2-n solution (CO ₃ Na ₂ ) up to pH value 7 Make up to 100 ml with water

This mixture is applied to 100% white hair for minutes. The hair are rinsed and washed with shampoo. A light gray beige is obtained.

B e i s ρ i e 1 6

Make the following mixture:

Methyl-y- [N- (2-nitro-4-methyl-5-amino) -phenyl] aminopropyl-

trimethylammonium sulfate 0.266 g,

l-N-methylamino-2-nitro-4-N '- / 3-aminoethylamino-

benzene monobromohydrate 0.435 g

Ethoxylated lauryl alcohol

with 10.5 mol of ethylene oxide 1.5 g

2-n solution (CO ₃ Na ₂ ) up to pH 9 Make up to 100 ml with water

This mixture is applied to light brown to dark blonde hair; one lets Leave on for minutes, rinsing and washing with a shampoo. You get a strong mahogany chestnut brown.

Example 7
The following dye is made:

1 -N, N-dimethylamino-3 - /? - amino-

ethylamino-4-nitrobenzene 0.2 g

Ethoxylated lauryl alcohol

with 10.5 moles of ethylene oxide 2.0 g

Citric acid in 5% solution up to

pH value 7

Make up to 100 ml with water

This mixture is applied to dark blonde hair; leave to act for 10 minutes, rinses and washes with shampoo. A bronze reflection is obtained.

Example 8

The following dye is made:

1-N, N-dimethylamino-3-y-dimethylaminopropylamino-4-nitrobenzene ... 0.40 g of ethoxylated lauryl alcohol

with 10.5 moles of ethylene oxide 2.0 g

Citric acid in 5% solution up to

pH value 7

Make up to 100 ml with water

This mixture is applied to auburn hair; let it act for 10 minutes, rinses and washes with shampoo. A golden chestnut brown is obtained.

Example 9

The following dye is made:

Methyl-y- [N- (2-nitro-5-dimethylamino) -phenyl] -amino-propyl-

trimethylammonium sulfate 0.37 g

Ethoxylated lauryl alcohol

with 10.5 mol of ethylene oxide 2 g

Sodium carbonate, 2-n solution up

pH 9

Make up to 100 ml with water

This mixture is applied to light chestnut colored hair; left for 10 minutes act for a long time, rinse and wash with a shampoo. A matt gold reflex is obtained.

Example 10

The following dye is made:

1- ^ N-Dimethylamino-S-y-dimethylaminopropylamino-4-nitrobenzene ... 0.23 g 1 -N-methylamino-2-nitro-4-N '- /? - aminoethyl-aminobenzene-

monobromohydrate 1.16 g

Ethoxylated lauryl alcohol

with 10.5 mol of ethylene oxide Ig

Sodium carbonate, 2-n solution up

pH 9

Make up to 100 g with water

This composition is applied to light auburn hair; let it act for 10 minutes, rinses and washes with shampoo. A chestnut brown tone is obtained.

Example 11 The following colorant is prepared:

l-N, N-dimethylamino-3- / S-amino-

ethylamino-4-nitrobenzene 0.04 g

l-N - ^ - Aminoethylamino-2-nitro-4-N ', N' - /? - hydroxy-ethylamino-

benzene monobromohydrate 0.27

Ethoxylated lauryl alcohol

with 10.5 moles of ethylene oxide 2.0 g

Citric acid, 4% solution, up to

pH value 7

Make up to 100 ml with water

This mixture is applied to 100% white hair; let it act for 15 minutes, rinses and washes with shampoo. A matt ash blonde is obtained.

Example 12 The following colorant is prepared:

Methyl-y- [N- (2-nitro-5-dimethylamino) phenyl] -amino-propyl-

trimethylammonium sulfate 0.20 g

l-N-methylamino-2-nitro-4-N '- /? - aminoethylamino-

benzene monobromohydrate 0.35 g

Ethoxylated lauryl alcohol

with 10.5 moles of ethylene oxide 4.0 g

Sodium carbonate 2-n solution up to

pH value 7

Make up to 100 ml with water

This mixture is applied to light auburn hair; let it act for 5 minutes, rinses and washes with shampoo. A light chestnut brown with a slight red-violet reflex is obtained.

Example 13 The following colorant is prepared:

1-amino-3-y-dimethylaminopropylamino-4-nitrobenzene mono-

chlorohydrate 0.23 g

Ethoxylated lauryl alcohol

with 10 moles of ethylene oxide 3.0 g

Sodium hydroxide, 5-n solution to pH ... 7.5

Make up to 100 ml with water

This mixture is applied to light chestnut colored hair; left for 10 minutes act, washes with a shampoo and rinses. A golden light chestnut brown is obtained.

Example 14

The following dye is made:

l-N ^ -Diethylamino-S-y-dimethylaminopropylamino-4-nitro-benzene-

monochlorohydrate 0.26 g

Ethoxylated lauryl alcohol

with 10.5 moles of ethylene oxide 3.5 g

Citric acid in solution from 20% to pH

Make up to 100 ml with water

This mixture is applied to light chestnut colored hair; left for 10 minutes

act for a long time, rinse and wash with shampoo. A bronze reflection is obtained.

B e i s ρ i e 1 15 The following dye is made:

l-N.N-diethylamino-S-y-dimethylaminopropylamino-4-nitro-benzene-

monochlorohydrate 0.05 g

l-N-methylamino ^ -nitro ^ -N'-methyl-N '^ / S-aminoethylamino-benzene-

monobromohydrate 0.20 g

Ethoxylated lauryl alcohol

with 10.5 moles of ethylene oxide 2.5 g

Sodium carbonate, 2-n solution up

pH value 8

Make up to 100 ml with water

This mixture is applied to 100% white hair; let it act for 15 minutes, rinses and washes with shampoo. A light chestnut brown is obtained.

B e i s ρ i e 1 16

The following dye is made:

1 -N, N-dimethylamino-3- / S-diethylamino-ethylamino-4-nitro-benzene-

monochlorohydrate 0.32 g

Ethoxylated lauryl alcohol

with 10.5 mol of ethylene oxide 4 g

Sodium carbonate, 2-n solution up

pH value 7

Make up to 100 ml with water

This mixture is applied to light chestnut colored hair; left for 10 minutes act, rinse and wash with shampoo. A matt gold reflex is obtained.

Example 17 The following dye is made:

1-Ν, Ν-dimethylamino-3-ß-diethylaminoethylamino-4-nitrp-benzene monochlorohydrate 0.062 g

l-N-ß-Aminoäthylammo-2-nitro-4-N'N '- /? - hydroxyäthylamino-

benzene monobromohydrate 0.188 g

Sodium carbonate, 2-n solution up

pH value 7

Make up to 100 ml with water

This mixture is applied to 100% white hair; let it act for 15 minutes, rinses and washes with shampoo. An ash blonde is obtained.

Example 18 The following colorant is prepared:

Methyl- / S- [N- (3-dimethylamino-4-nitro-6-methyl) -phenyl] -amino- ethyl methyl diethyl ammonium

sulfate 2.0 g

Ethoxylated lauryl alcohol

with 10.5 moles of ethylene oxide 5.0 g

2-n solution (CO _? Na ₂ ) up to pH 10 Make up to 100 ml with water

This solution is applied to 100% white hair at room temperature for 10 minutes.

The hair is then rinsed and washed with shampoo. A strong yellow color is obtained Coloring.

B e i s ρ i e 1 19 The following dye is made:

Methyl - /? - [N- (3-dimethylamino-4-nitr o-6-methyl) -phenyl] -aminoethyl-methyl diethylammonium sulfate 0.067 g of l-diethylaminoethylamino-2-nitro-4-N, N-dihydroxyäthylamino-

benzene dichlorohydrate 0.328 g

Iso-octylphenyl-polyethoxy-

ethanol 4.0 g

Make up to 100 ml with water

This mixture is applied to 90% white hair; let it act for 15 minutes, washes with shampoo and rinses. A light chestnut brown is obtained.

609 543/400

Claims (1)

Patent claims: 1. Means for coloring human hair, consisting of an aqueous solution at least a substituted nitrophenylenediamine and optionally other hair dyes and usual Additives, characterized that the substituted nitrophenylenediamine is a compound of the formula