DE29714795U1 - Means for coloring and tinting human hair - Google Patents

Description

A-32/971/

Products for coloring and tinting human hair

The present invention relates to a composition for dyeing or tinting human hair, which simultaneously provides a
Hair coloring with increased color intensity, without damaging the hair, but on the contrary, has a conditioning,
particularly on the mechanical properties of the hair such as its elasticity and also its volume-enhancing effect.

It is generally known that hair dyes are divided into two categories: on the one hand, permanent hair dyes, which basically contain hair dye precursors which, together with oxidizing agents, develop the desired color on the hair depending on their composition; and on the other hand, semi-permanent hair dyes, which contain direct,
mostly contain cationic dyes, which do not require any oxidizing agent to develop their coloring performance. Accordingly, the dyes are also
less durable than those with permanent dyes
achievable.

These colour compositions based on direct dyes are usually sold either as tinting shampoos,
-lotions or as a tint fixative, possibly also as an aerosol foam.

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The invention is therefore based on the task of creating a hair dye containing at least one direct cationic hair dye which not only has no hair-damaging effect, but also has a conditioning effect on the hair, in particular improves its mechanical properties and volume, and increases the shine and stability as well as the intensity of the hair coloring achieved.

The solution to this problem consists in adding to a hair dye containing at least one direct hair dye at least one compound of the general formula I

R ² OH ₂ C -CH-OH

I (D

CH-CH,

I
N-(CH) _n -OH

I
R ¹ - C

■ The

■ ■ y

wherein R ¹ and R ² are identical or different alkyl or alkenyl radicals having 10 to 22 carbon atoms, and η is a number from 1 to 3.

This not only prevents possible hair damage, especially when used several times in quick succession, but also gives the colored hair additional bounce, volume and elasticity. In addition, a deeper color effect is achieved.

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These compounds are basically known from EP-A 227 994. They are described there as humectants for cosmetics.

Preferred compounds of formula I in the context of the invention

are those in which the radicals R ¹ and R ² are a C ₁₂ -C ₁₈ alkyl group mean.

A particularly preferred compound of formula I is

those in which R ¹ is a C ₁₆ H ₃₃ - and R ² is a C ₁₅ H ₃₁ -

alkyl radical and &eegr; 2. The proportion of this compound is preferably 0.001 to

2.5, in particular 0.005 to 1 wt.%, for example 0.01 to 0.5% by weight, calculated on the total composition of the agent according to the invention.

According to a preferred embodiment of the invention, the agents according to the invention contain the compound of formula (I) in the form of a nanoemulsion which has a corresponding content of the same, in particular N-(3-hexadecyloxy-2-hydroxypropyl)-N-2-hydroxyethylhexadecanamide.

By using it in a nanoemulsion, this active ingredient can be particularly well incorporated into aqueous carrier systems.

When the composition is applied to the hair to be treated, the active ingredient is evenly distributed and can take effect after the nanoparticles have broken down. - .

_4_

The production of the nanoemulsion containing the active ingredient
is carried out in a conventional manner by high pressure homogenization
in a microfluidizer, preferably under
Use of phospholipids, especially lecithin, as
Capsule wall material.

A suitable method is described, for example, by E. Mayhew et
al., Biochimica et Biophysica Acta, Vol. 775 (1984), pp. 169 174,
and in the publication by J. Gareiß et al., Parfümerie
and Cosmetics, No. 10/1994, pp. 652 - 659.

The average particle diameter of a particle in the
Nanoemulsion used in the inventive agents is
between about 10 and about 600 nm, preferably between about 25 and about 300 nm, in particular about 40 and about 200 nm.

The compositions according to the invention can be in the form of a solution, dispersion, emulsion, gel, aerosol foam or powder.

In principle, all direct dyes approved for this purpose can be used as direct hair dyes with which semi-permanent hair coloring, also known as tinting, is achieved; reference is made in particular to the German "Regulation on cosmetic products (Cosmetics Regulation)" in the currently applicable version, Annex 3.

Particularly suitable basic (cationic) dyes that are preferred are:

·»· I t ti ···

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Basic Blue 6, C.I. No. 51,175;

Basic Blue 7, C.I. No. 42,595;

Basic Blue 9, C.I. No. 52,015;

Basic Blue 26, C.I. No. 44,045;

Basic Blue 41, C.I. No. 11,154;

Basic Blue 99, C.I. No. 56,059;

Basic Brown 4, C.I. No. 21,010;

Basic Brown 16, C.I. No. 12,250;

Basic Brown 17, C.I. No. 12,251;

Basic Green 1, C.I. No. 42,040;

Basic Red 2, C.I. No. 50,240;

Basic Red 22, C.I. No. 11,055;

Basic Red 76, C.I. No. 12,245;

Basic Violet 1, C.I. No. 42,535;

Basic Violet 3, C.I. No. 42,555;

Basic Violet 10, C.I. No. 45,170;

Basic Violet 14, C.I. No. 42,510;

Basic Yellow 57, C.I. No. 12,719.

Less preferred acidic (anionic) dyes may be used:

Acid Black 1, C.I. No. 20,470;

Acid Blue 9, C.I. No. 42,090;

Acid Blue 74, * C.I. No. 73,015;

Acid Red 18, C.I. No. 16,255;

Acid Red 27, C.I. No. 16,185;

Acid Red 87, C.I. No. 45,380;

Acid Red 92, C.I. No. 45,410;

Acid Violet 43, C.I. No. 60,730;

Acid Yellow 1, C.I. No. 10,316;

Acid Yellow 23, C.I. No. 19,140;

Acid Yellow 3, C.I. No. 47,005;

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D&C Brown No.1, C.I. No. 20,170;

D&C Green No.5, C.I. No. 61,570;

D&C Orange No.4, C.I. No. 15,510;

D&C Orange No.10, C.I. No. 45,425:1;

D&C Orange No.11, C.I. No. 45,425;

D&C No.21, . C.I. No. 45,380:2;

D&C Red No.27, C.I. No. 45,410:1;

D&C Red No. 33, C.I. No. 17,200;

D&C Yellow No.7, C.I. No. 454,350:1;

D&C Yellow No.8, C.I. No. 350;

FD&C Red No.4, C.I. No. 14,700;

FD&C Yellow No.6, C.I. No. 15,985.

Vegetable dyes can also be used alone or in combination with synthetic direct dyes, for example henna (red or black), alkanet root, laccaic acid (stick varnish), logwood powder, madder root and rhubarb root powder, etc.

The proportion of direct dyes in the ready-to-use compositions used according to the invention is variable depending on the desired color and can generally be between about 0.001 to about 5, preferably 0.01 to 2.5, in particular 0.1 to 1.5% by weight of the agent.

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The concentration is of course dependent on the application form of the agent, i.e. if it is in the form of a powder that must be diluted with water before use, the dye concentration in the powder is of course correspondingly higher than in an aqueous solution or dispersion. Suitable powdered hair dyes containing direct hair dyes are also known per se, for example from DE 195 30 998 Al, to which reference is made. These color powders must of course be mixed with water before use.

The compositions according to the invention can, in particular as coloring hair conditioners or leave-on products, preferably also contain at least one cationic surfactant, in particular in an amount of 0.1 to 7.5, preferably 0.25 to 5, particularly preferably 0.5 to 2.5% by weight of the total composition.

Suitable long-chain quaternary ammonium compounds that can be used as cationic surfactants alone or in a mixture with one another are in particular cetyltrimethylammonium chloride, dimethyldicetylammonium chloride, trimethylcetylammonium bromide, stearyltrimethylammonium chloride, dimethylstearylbenzylammonium chloride, benzyltetradecyldimethylammonium chloride, dimethyldihydrogenated tallow ammonium chloride, laurylpyridinium chloride, lauryldimethylbenzylammonium chloride, lauryltrimethylammonium chloride, tris(oligooxyethyl)alkylammonium phosphate, cetylpyridinium chloride, etc.

The quaternary ammonium salts disclosed in EP-A 472 107 are also very suitable.

In principle, all quaternary ammonium compounds as listed in the "CTFA International Cosmetic Ingredient Dictionary", 4th Ed. (1991), under the trivial name "quaternium", are suitable.

The composition can of course also contain the usual ingredients in such conditioning agents; to avoid repetition, reference is again made to K. Schrader, "Grundlagen und Rezepturen der Kosmetika", 2nd edition (1989), pp. 722 - 771.

The hair dyes according to the invention can contain the substances customary in such aqueous preparations.

These are, for example, synthetic or natural hair conditioning polymers, preferably in an amount of 0.1 to 2.5, in particular 0.25 to 1.5 wt.% of the total composition.

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In addition to the well-known quaternary cellulose derivatives of the "Polymer JR" type, suitable cationic polymers include in particular quaternized homo- and copolymers of dimethyldiallylammonium chloride, as sold under the trade name "Merquat", quaternary vinylpyrrolidone copolymers, in particular with dialkylaminoalkyl (meth)acrylates, as sold under the name "Gafquat", copolymers of vinylpyrrolidone and vinylimidazolinium methochloride, which are sold under the trade name "Luviquat", polyamino-polyamide derivatives, for example copolymers of adipic acid-dimethylaminohydroxypropyldiethylenetriamine, as sold under the name "Cartaretine F", as well as bisquaternary long-chain ammonium compounds of the urea structure described in US Pat. No. 4,157,388, which are sold under the trade name "Mirapol A 15" are available on the market.

In this context, reference is also made to the 'cation-active' polymers mentioned in DE-OSs 25 21 960, 28 11 010, 30 44 738 and 32 17 059 as well as the products described in EP-A 337 354 on pages 3 to 7. Mixtures of different cationic polymers can also be used.

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Instead of the cationic polymers or in combination with them, non-ionic polymers can also be used. Suitable non-ionic polymers are mainly vinylpyrrolidone homo- and copolymers, in particular polyvinylpyrrolidone itself, copolymers of vinylpyrrolidone and vinyl acetate or terpolymers of vinylpyrrolidone, vinyl acetate and vinyl propionate, such as those sold by BASF under the trade name "Luviskof".

However, (co)polymers made from various acrylic and methacrylic esters, acrylamide and methacrylamide, for example polyacrylamide with molecular weights of over 100,000, dimethylhydantoin-formaldehyde resins, etc., can also be used. Of course, mixtures of various non-ionic polymers can also be used.

Finally, amphoteric polymers are also suitable, e.g. the copolymers sold under the name "Amphomeir" made from N-octylacrylamide, N-butylaminoethyl methacrylate and acrylic acid.

These polymers are particularly found in colour fixatives.

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The colorants according to the invention can contain the additives that are usual in such compositions, the type and nature of which depends on the application form of the agent. These are fats, fatty alcohols, emulsifiers, pH regulators, solvents and binding agents, solubilizers, preservatives, perfumes, etc.

Emulsions or dispersions contain, for example, fats and oils, which also include waxes, in particular natural oils such as avocado oil, coconut oil, palm oil, sesame oil, peanut oil, sperm oil, sunflower oil, almond oil, peach kernel oil, wheat germ oil, macadamia nut oil, evening primrose oil, jojoba oil, castor oil, or even olive or soy oil, lanolin and its derivatives, as well as mineral oils such as paraffin oil and Vaseline.

Synthetic oils and waxes include silicone oils, polyethylene glycols, etc.

Other suitable hydrophobic components in emulsions and dispersions are in particular fatty alcohols, preferably those with about 8 to 22 carbon atoms in the molecule such as myristyl, cetyl, stearyl alcohol, wax alcohols and fatty acid esters such as isopropyl myristate, palmitate, stearate and isostearate, oleyl oleate, isocetyl stearate, hexyl laurate, dibutyl adipate, dioctyl adipate, myristyl myristate, oleyl erucate, polyethylene glycol and polyglyceryl fatty acid esters such as PEG-7 glyceryl cocoate, cetyl palmitate, etc.

A-32/97 -12-

These hydrophobic components can be contained in the compositions according to the invention preferably in a total amount of about 0.5 to about 10, in particular about 1 to 7.5, especially about 1.5 to 5 wt.%, calculated on the total composition.

A summary of the production of such agents can be found in the aforementioned monograph by K. Schrader, pp. 798 to 815, especially pp. 804 ff.

As mentioned at the beginning, the colorants according to the invention are preferably in the form of a powder, emulsion, dispersion or (optionally thickened, i.e. gel) solution and can also be packaged as an aerosol foam. These compositions and their production are generally known to the person skilled in the art and therefore require no further explanation. Tinting shampoos contain the usual shampoo ingredients, in particular surfactants. These are known from the prior art and are also described, for example, in Schrader, I.e., pp. 677-722.

The pH value of the hair dyes according to the invention is preferably between 3 and 7, in particular between 4 and 6.5.

-13-

The following examples describe the composition of the agents according to the invention.

Color gloss rinses of the following compositions were prepared by simply mixing the ingredients.

example 1 Colour fixer

Dimethylhydantoin-formaldehyde resin 2.30 (wt.%) Vinyl acetate/crotonic acid copolymer 1.00

Nanoemulsion 1 containing a 1.05

Compound of formula I
(R^C ₁₆ H ₃₃ ; R ² = C ₁₅ H ₃₁ ; η = 2)

Cetrimonium bromide 0.10

Polyethylene glycol-32 0.30

ethanol 34,00

Aminomethylpropanol 0.06

Benzophenone-4 0.02

Perfume 0.40

Basic Blue 2^2 0.08

Basic Brown 17 0.03

Basic Brown 16 0.02

Basic Yellow 57 0.02

Basic Red 76 0.01 water ad 100.00

Using this color fixer resulted in shiny, medium brown colored hair with improved shine and volume.

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Omitting the compound according to formula I resulted in a significantly paler coloration with reduced gloss and elasticity.

Composition of Nanoemulsion 1

By high-pressure homogenization in a microfluidizer, a homogeneous nanoemulsion was obtained in a known manner, which had the following composition:

Stage 1 :

Lecithin N-Cetylisopropanol-Palm.itamide MEA Glycerin

Avocadin® (Avocado oil unsaponifiables) Ethanol
Diisopropyl adipate

5, 0 (wt.%) 4, 0 8th, 0 8th, 0 10, 0 2, 5

Stage 2 :

Water @ 100.0 (wt.%)

The particle size was 100 ± 30 nm.

-15-

Example 2 Color Foam Conditioner

Cocoamidopropyl betaine 5.00 (wt.%)

Diethylene glycol 5.00

Oleth-5 9.0

Cetylstearyl alcohol 0.70

Wheat protein hydrolysate 0.40

Hydroxyethylcellulose 0.30

Ammonium chloride 0.25

Panthenol 0.20

PEG—40 hydrogenated castor oil 0.20

Coconut fatty acid monoethanolamide 0.30

Perfume 0, 20

Preservative 0.10

Ethanolamine 0.03 Nanoemulsion 1, containing a

Compound of formula I 0.25 (R^C ₁₆ H ₃₃ ; R ² = C ₁₅ H ₃₁ ; η = 2)

Basic Brown 16 0.40

HC Red No. 3 0.35

Basic Blue 99 0.35

HC Yellow No. 5 0.25 water to 100.00

94 wt.% of this composition was filled into an aerosol can with 6 wt.% propane/butane propellant.

When applied to the hair, a shiny chestnut brown color was obtained.

Omitting the compound according to formula I resulted in a less intense and shiny color.

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Example 3 1,2-Propanediol 3.00 Color conditioner Cetylstearyl alcohol 1.25 Hydroxyethylcellulose 1.00 Silicone oil 0.20 Methylparaben 0.20 Cetyltriethylammonium chloride 0.20 Dicetyldimethylammonium chloride 0.50 Henna extract 0.50 Perfume 0.50 Benzophenone-4 0.40 Lauryldimethylamine oxide 1.00 Nanoemulsion 1 containing a Compound of formula I 0.50 (R ¹ S=C ₁₆ H ₂₃ ; R ² = C ₁₅ H ₃₁ ; η = 2) Basic Red 76 0.10 Basic Blue 0.01 Citric acid .■..·.■:-.. q.s. Water .. . . ad 100.00

This composition produced a shiny, intense red tone on the hair, which was noticeably paler when the compound of formula I was omitted.

In addition, the hair without the Formula I compound had a noticeably rougher feel.

· I

27 ,00 (wt.%) 7 ,50 9 ,00 6 ,00 3 ,50 1 ,00 1 ,00 O ,30 O ,50

-17-

Example 4 Tinting Shampoo

Disodium lauryl ether sulfosuccinate (30%) 27.00 (wt.%)

Sodium lauroyl sarcosinate (30%) Cg-C^-alkyl polyglycoside (&khgr;= 1.35),

Dimethyllaurylamine oxide (35%) Laurylhydroxysulphobetaine (30%) Polyethylene glycol-160-sorbitan tristearate

Polysorbate 60

Preservatives (parabens) Complexing agents (EDTA)

Cationic polymer

(Polydimethyldiallylammonium chloride) 0.50 Nanoemulsion 1, containing a

Compound of formula I 0.35

(R^C ₁₆ H ₃₃ ; R ² = C ₁₅ H ₃₄ ; η = 2)

Citric acid 1.00

Henna extract 0.10

Basic Yellow Sl 0.01

Basic Red 76 0.08

Basic Blue 99 0.01

Water ad 100,00

Using this tinting shampoo gives the hair a shiny, intense red tone and a pleasant feel.

Omitting the compound according to formula I resulted in a noticeably paler color and a rougher feel.

Example 5 Color powder

Hydroxypropyl Guar 14.00 (wt.%)

Cyclodextrin in 3.50

PEG-1500 20.00 Compound of formula I

(R ¹ S=C ₁₆ H ₃₃ ; R ² =C ₁₅ H ₃₁ ; n=2) 0.15

Fatty alcohol polyglycol ether (6 EO) 7.00

Fatty alcohol polyglycol ether (50 EO) 6.00

Wheat protein hydrolysate 2.40

Honey dry extract 3.00

Strength 38.00

Potassium sorbate 3.15

C.I. No. 56,059 0.65

C.I. No. 12,250 2.00

C.I. No. 12,251 0.15

After diluting with water in a ratio of 1:12, the resulting mixture was applied to the hair and, after 20 minutes of exposure, rinsed and dried.

A shiny, light blonde color was obtained. Omitting the compound of formula I resulted in a less intense, somewhat dull-looking hair color.

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Example No. 6 Color lotion

1,2-Propanediol 3.00 (wt.%)

Cetylstearyl alcohol 1.25

Hydroxyethylcellulose 1.00

Silicone oil 0.20

Methylparaben 0.20

Cetyltrimethylammonium chloride 0.20

Dicetyldimethylammonium chloride 0.50

Henna extract 0.50

Perfume 0.50

Benzophenone-4 0.40

Lauryldimethylamine oxide 1.00

Nanoemulsion 1 containing 0.30 compound of formula I
(R^C ₁₆ H ₃₃ ; R ² =C ₁₅ H ₃₁ ; n=2)

Basic Red 76 0.10

Basic Blue 99 0.01

Citric acid q.s. water ad 100.00

The composition was applied to the hair, massaged in and left there.

A shiny red color was obtained.

An identical composition, but without the nanoemulsion with a compound of formula I, resulted in a less intense coloration.

Example ad 7 1.00 (wt.%) Color gel 0.80 Hydroxypropyl Guar 1.00 Polyquaternium-7 0.10 Cocoamidopropyl betaine 5.00 Dimethicone Copolyol 0.20 Ethanol 0.50 Perfume Nanoemulsion 1, containing a compound of the formula I 0.066 (R ^l =C ₁₆ H ₃₃ ; R ² =C ₁₅ H ₃₁ ; n=2) 0.050 Basic Blue 99 0.004 Basic Brown 17 0.015 Disperse Black 9 0.060 Disperse Blue 3 100.00 HC Red No. 3 Water

A shiny, intense light brown hair color was achieved.

Omission of nanoemulsion 1 resulted in products whose color intensity, measured after 30 minutes of exposure at 30°C, was on average 25% lower than that achieved with the composition according to the invention.

Claims (3)

A-32/97 U Protection claims 1.Products for colouring and tinting human hair _/ containing at least one direct cationic hair dye, characterized in that it contains at least one compound of the formula I, R ² OH ₂ C -CH-OH I (D _CH2 I
N-(CH ₂ I-OH R ¹ - C wherein R ¹ and R ² represent identical or different alkyl or alkenyl radicals having 10 to 22 carbon atoms and is a number from 1 to 3. 2. Agent according to claim 1, containing 0.001 to 2.5% by weight of at least one compound of formula I, calculated on the total composition of the agent. 3. Agent according to one of claims 1 and/or 2, containing 0.005 to 1% by weight of at least one compound of formula I, calculated on the total conversion of the agent.