DE20010877U1 - Means for coloring human hair - Google Patents

Description

α-18/00 —UL

Agents for coloring human hair

The present invention relates to an agent for coloring human hair based on oxidation dyes, which has an excellent coloring effect, in particular produces a uniform color with good stability, has no damaging effect on the hair structure even after repeated use, but rather has a conditioning effect and produces an expressive color shine.

As is known, oxidation hair coloring requires the prior mixing of two compositions of oxidation dye precursor and oxidizing agent, kept separate until application, and the subsequent application of the resulting mixture.

These compositions are usually used at a pH value between about 8 and 11, especially 9 to 10.5, which can lead to hair damage if used repeatedly and in close proximity to one another. In addition, the color effect, especially the color stability and uniformity of the color, can still be improved.

It has now been found that these disadvantages can be overcome and a hair dye based on at least one oxidation dye precursor, preferably a developer-coupler system, which has a uniform coloring effect and does not damage the hair structure in any way, but gives the colored hair shine and makes it easy to comb, can be produced by adding to this agent at least one

Organopolysiloxane in which at least one silicon atom is bonded via an alkylene group having a heteroatom, in particular a nitrogen atom, to a poly-(N-acylalkyleneimine) having units of the formula I

-(CH ₂ )- N- (I)

I
RC = O

where η is a number from 1 to 5 and R is hydrogen, a Ci-C^-alkyl or cycloalkyl, aralkyl or aryl group, preferably in an amount of 0.01 to 5 wt.%, in particular 0.05 to 2.5 wt.%, based on the total amount of the agent.

Preferred organopolysiloxane polymers are those as described in EP-A 640 643, in particular optionally quaternized aminoalkyl, in particular aminopropyldimethylpolysiloxane/polyethyloxazoline copolymers of the formula

_CH3

_CH3 "

ISiO

(CH ₂ ) _x IH ₂ N©-

_CH3

SiO

CH-CH,

_CH3

I
- Si - CH ₃

_CH3

_{CH2 - CH2_N}

—R

yC = O

I
_{C2H5 ​}

·

·

-3-

wherein m and η are each integers from 20 to 10,000, in particular 50 to 7,000, especially 100 to 5,000, x is a number between 1 and 5, preferably 3, and y is a number from 5 to 30, R is a C-i-C^-alkyl or aryl group, in particular a methyl, ethyl or benzyl group, and Y" is an anion.

The preparation of the aminoalkyldimethylpolysiloxane/polyethyloxazoline graft copolymers preferably used according to the invention is described in the aforementioned EP-A 640 643 and is carried out according to the following scheme:

_{C2H5 ​}

_{C2 H5 -} ( _{NCH2 CH2} ) - I x-1

^C = ° C ₂ H ₅

_{C2H5 ​}

C ₂ H ₅ SO ₄

_{CH3 CH3}

CH-CH,

CH-CH,

H ₃ C - SiO(SiO ) — (SiO)-Si-CH ₃

_CH3

_CH3

H ₃ CH ₂ CH ₂ CH ₂ NH ₂

•♦ ··

_{CH3CH3CH3 ​ ​}
III

H ₃ C - SiO (SiO) _m (SiO) _?
The
_{CH3 CH3}

_CH3

Si

^CH3

_CH3

CH ₂ CH ₂ CH ₂ NH ₂ -(CH ₂ CH ₂ N) _x -C ₂ H ₅

&thetas;&igr;

O=C
|
_{C2H5 ​}

The anion Y" of the general formula can of course also be another
than the ethyl sulfate anion of the above example, ie the
Quaternization can also be carried out with methyl chloride, dimethyl sulfate, benzyl chloride,
Dodecyl bromide etc.

A particularly preferred graft copolymer of the type shown has a total molecular weight of about 50,000 to about 500,000, preferably about 80,000 to about 300,000, in particular about 100,000 daltons, the molecular weight of the oxazoline segment being about 2,500 to about 7,500, preferably about 4,000 to about 6,000, in particular about 5,000 daltons/segment, i.e. the molar fraction is 20 units/molecule. The preferred Si content is, according to elemental analysis, about 50%.

Particularly suitable are the organopolysiloxanes described under the names A-1, A-2 and A-3 on pages 12 to 13 of EP-A 640 643. The proportion of graft copolymers in the hair dyes according to the invention is about 0.05 to 5, preferably 0.1 to 2.5, in particular 0.5 to 1.5% by weight of the total composition.

Ir

VIII

xVV

-5-

The polymers added according to the invention can preferably be added to the composition containing the oxidation dye precursor; however, it is also possible to use them in the oxidizing agent composition or in both.

These compositions are known per se from the state of the art and are described, for example, in the monograph by K. Schrader, Fundamentals and Recipes of Cosmetics, 2nd edition (Hüthig Buchverlag, 1989), pp. 782-804.

As already indicated, the pH of the ready-to-use composition is preferably in the alkaline range between about 8 and 11, in particular about 9 to 10.5, but it may also be in the weakly acidic (about 5 to 6.9, in particular about 5.5 to 6.5) or neutral range.

The possibly slightly weaker color intensity in the acidic range is
is significantly increased by the polymer additive according to the invention.

As already mentioned, in principle all developer and coupler substances known from the state of the art for hair coloring can be used.

Examples of developer substances are in particular 1,4-diaminobenzene,
2,5-diaminotoluene, tetraaminopyrimidines, triaminohydroxypyrimidines,
1,2,4-triaminobenzene, 2-(2,5-diaminophenyl)ethanol, 4-aminophenol, 4-amino-3-methylphenol,
2-(2-hydroxyethylamino)-5-aminotoluene and 1-amino-4-bis-(2'-hydroxyethyl)-aminobenzene
or their water-soluble salts; exemplary

-6-

Coupler substances are resorcinol, 2-methylresorcinol, 4-chlororesorcinol, 2-amino-4-chlorophenol, 4-(N-methyl)aminophenol, 2-aminophenol, 3-aminophenol, 1-methyl-2-hydroxy-4-aminobenzene, 3 -N,N-dimethylaminophenol, 4-amino-3-methylphenol, 5-amino-2-methylphenol, 6-amino-3-methylphenol, 3-amino-2-methylamino-6-methoxypyridine, 2-amino-3-hydroxypyridine , 4-aminodiphenylamine, 4,4'-diaminodophenylamine, 2-dimethylamino-5-aminopyridine, 2,6-diaminopyridine, 1,3-diaminobenzene, 1-amino-3-(2'-hydroxyethylamino)benzene, 1-amino- 3-[bis(2'-hydroxyethyl)amino]benzene, cc-naphthol, 1 ^-diamino^-chloro-benzene, 4,6-dichlororesorcinol, 1,3-diaminotoluene, 4-hydroxy-1,2-methylenedioxybenzene, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1, 7-Dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1-hydroxynaphthalene, 4-hydroxy-1,2-methylenedioxybenzene, 2,4-diamino-3-chlorophenol and/or 1-methoxy-2-amino-4-(2'- hydroxyethylamino)benzene, although this exemplary list cannot claim to be complete.

Developer and coupler substances are preferably contained in a molar ratio of 1:3 to 5:1, in particular about 1:1 and about 3:1; their proportion in the color mixtures used according to the invention can be about 0.25 to about 5% by weight, depending on the desired coloration.

Diluted hydrogen peroxide solutions, emulsions or gels are mainly used as oxidizing agents. It is also possible, but less common, to use other peroxides such as alkaline earth peroxides, urea peroxide, melamine peroxide, etc. in appropriate stoichiometric amounts.

♦♦·· ■·

-7-

The oxidation dye compositions can be used as solutions, creams, pastes, gels, aerosols, etc.

The exposure time on the hair is preferably about five to thirty minutes, in particular about 10 to 20 minutes, for example 15 minutes each for the alkaline and acidified color mixture. The method according to the invention is suitable both for the holistic, i.e. initial coloring of the hair, and for re-coloring.

The agents used according to the invention can of course contain all substances customary in hair dyes, a detailed list of which is omitted here, and can be in the form of (aqueous) solutions, emulsions, creams, foams, etc.

It is also possible to use direct hair dyes to achieve the desired shades.

To avoid repetition, reference is made to the state of the art, as described, for example, in the monograph by K. Schrader, I.e.

The compositions and individual components disclosed therein, to which express reference is made, can also be used within the scope of the present invention.

The following examples serve to illustrate the invention.

·

·

A-18/00 -8- Example 1

On strands of bleached human hair, a dye composition was applied which was prepared by mixing equal parts by weight of a 6% hydrogen peroxide solution and an oxidation dye precursor of the following

composition and had a pH of 9.8.

Carrier mass

Cetylstearyl alcohol 11.00 (wt.%)

Oleth-5 5.00

Oleic acid 2.50

Stearic acid monoethanolamide ^,50

Coconut fatty acid monoethanolamide 2.50

Sodium lauryl sulfate 1.70

Sodium sulphite 1.00

1,2-Propanediol 1.00

Ascorbic acid 0.50

Ammonium chloride 0.50

EDTA, tetrasodium salt 0.20

Perfume 0.40

Wheat protein hydrolysate 0.20

Silica 0.10

Alkyldimethylpolysiloxane/Poly-0> ⁴⁰

ethyloxazoline graft copolymer

(Organopolysiloxane

A-1 of EP-A 640 643)

· ·
* · ·· * · · · ■
···· ·· ·. • · · · ·· •
•
• •
• ► · ·· ·
· » · • ·
* · *
·· · * •
•
« ·

A-18/00 -9-

Oxidation dye mixture

2,5,6-Triamino-4-hydroxypyrimidine sulfate ^>^ ¹

2,5-Diaminotoluenesulfate ®>^5

4-Chlorresorcinol ®>^

Resorcinol 0.05

3-Aminophenol °> ⁰³

Ammonia 9- ^s ·

Water ad 100.0

After 20 minutes of exposure, the hair was washed, rinsed and dried. A shiny, intense, even medium blonde color was obtained.

The omission of the graft copolymer resulted in a significantly less intense and uniform coloration with reduced gloss.

In addition, both wet and dry combability as well as the feel of the hair were significantly worse.

·

α-18/00 -10-

Example 2

The following oxidation dye mixture was introduced into a carrier mass corresponding to the composition of Example 1, but containing as polymer only 0.1% by weight of an organopolysiloxane according to Example A-2 of EP-A 640 643:

2,5,6-Triamino-4-hydroxypyrimidine sulfate 0.01 (% by weight)

2,5-Diaminotoluene sulfate 0.90

2-Amino-4-hydroxypyridine 0.80

1-Naphthol 0.17

3-Aminophenols 0.10

Resorcinol 0.03

This product was mixed with 6% H2O2 solution in a weight ratio of 1:1 (pH 9.5) and applied to strands of bleached human hair.

After 20 minutes of exposure, the hair was rinsed with water, shampooed and dried.

An intense, shiny, even mahogany color was obtained.

After applying a composition without the polymer, the hair not only had a less intense and uniform color, but also a rough feel.

A-18/00 -11-

Example 3

The composition described in Example 1 was varied in that it contained 1.0 wt.% organopolysiloxane polymer A1 according to EP-A 640 643 and was adjusted so that a pH of 6.5 was achieved when mixed with 6% H ₂ O2 solution.
The coloring was carried out as described. Once again, an even, intense, shiny blonde color was achieved.

Omission of the polymer not only resulted in deteriorated hair properties such as rougher feel, wet and dry combability and reduced elasticity, but above all in significantly reduced color intensity, uniformity of coloring and less shine.

Example 4

The following oxidation dye mixture was introduced into a carrier mass corresponding to the composition of Example 1, but which did not contain any organopolysiloxane:

2,5-Diaminotoluene sulfate 0.80 (wt.%)

Resorcinol 0.30

2-Amino-4-hydroxypyridine 0.06

3-Aminophenol 0.03

This product was mixed with 2% H ₂ O ₂ lotion in a weight ratio of 1:2 (pH 9.6) and applied to strands of bleached human hair.

After 20 minutes of exposure, rinse thoroughly and dry.

A shiny, even, intense reddish-brown color was obtained that remained stable even after five washes, leaving the hair soft and loose to the touch.

Composition of Hg O g-Lotion:

Disodium hydrogen phosphate

^{a H} 0.1 (wt.%)

Etidronic acid 0.3

Triethanolamine lauryl sulfate 0.7

Poloxamer ^R 407 1.0

PEG-7-Glycerylco(sat 0.5

Hydrogen peroxide 2.0

Alkyldimethylsiloxane/polyethyloxazoline graft copolymer 1.5 (organopolysiloxane A-1 of EP-A 640 643)
Water ad 100.0

Use of the H ₂ O2 lotion without the organopolysiloxane polymer, replaced by the same amount of a common polymer, Polyquaternium-7, resulted in a significantly reduced intensity and uniformity as well as reduced gloss of the coloration.

·

·

Claims (4)

1. Agent for dyeing human hair, containing a) at least one oxidation dye precursor, and b) at least one organopolysiloxane in which at least one silicon atom is bonded via an alkylene group having a heteroatom, in particular a nitrogen atom, to a poly(N-acylalkyleneimine) having units of the formula I


where n is a number from 1 to 5 and R is hydrogen, a C ₁ -C ₁₂ alkyl, cycloalkyl, aralkyl or aryl group. 2. Agent according to claim 1, containing as organosiloxane an optionally quaternized aminoalkyldimethylpolysiloxane/polyethyloxazoline copolymer of the formula


wherein m and n are each integers from 20 to 10,000, in particular 50 to 7,000, especially 100 to 5,000, x is a number between 1 and 5, preferably 3, and y is a number from 5 to 30, R is a C ₁ -C ₁₂ alkyl or aryl group, in particular a methyl, ethyl or benzyl group, and Y is an anion. 3. Agent according to claim 1 or 2, containing 0.05 to 5 wt.%, calculated on the total composition, of the organopolysiloxane. 4. Agent according to claim 3, containing 0.1 to 2.5 wt.% of the organopolysiloxane, calculated on the total composition of the agent.