DE1939255A1 - Solvent coloring - Google Patents

Description

PATENT LAWYERS

D RI MAAS
D RW PFEIF FFR

DR. F. VOITHENLEITNER

8 MUNICH 2 3
UNGERERSTR. 25 - TEL. 39 02 36

B 10 509

Revlon Inc., New York, N.Y., V. St. A.

Solvent coloring

The invention relates to the coloring of keratin fibers such as animal and human hair, and particularly relates to a solvent dyeing process in which a formamide derivative is used as the solvent.

The method of solvent staining by Peters and Stevens, J ₁ . Soc. Dyers & Colourists 72, 100, 241, 287 (1956), in deji British Patents 826,479 and 918,597 and in U.S. Patent 3,261,754, relates to the coloring of living human hair with conventional dyes at room temperature using an organic solvent as an essential component of the colorant. U.S. Patent 3,261,754 describes the properties that such solvents are said to have in order to be useful for this purpose, as well as tests for

909886/1 520

BAD ORfQlMAL

Determination of suitability of a solvent for the staining process indicated.

Of the many staining solvents specified, benzyl alcohol and tetraethyl urea give the best staining results. Benzyl alcohol, however, has the disadvantage that it discolors the skin and irritates the scalp caused. Tetraethylurea has the disadvantage of a strong pungent odor that is transmitted to the hair and can hardly be covered with perfume or removed by washing.

The invention is intended to overcome the disadvantages of the previously known coloring solvents.

The subject of the invention "is an aqueous hair dye composition, which is formed by an effective coloring amount of a dye and about 0.5 to 10 <$> of a formamide derivative of the formula

• ι ^ ^R 1

H-C- ΝΓ

is characterized in which R., a hydrogen atom, a lower alkyl radical, lower alkenyl radical or cycloalkyl radical or a hydroxy-substituted lower alkyl radical, lower alkenyl radical or cycloalkyl radical and Rp a lower alkyl radical, lower alkenyl radical or cycloalkyl radical or a hydroxy-substituted lower alkyl radical, means lower alkenyl radical or cycloalkyl radical.

^ßAD ORIGINAL 909886/1520

In the formula given above, the lower alkyl groups and lower alkenyl groups contain 1 to 6 carbon atoms and the cycloalkyl groups contain 5 to 6 carbon atoms. The total number of carbon atoms of both radicals R. and R ₂ is preferably 6 to 10 and in particular 6 to 8. The following formamides are particularly preferred: N-cyclohexylformamide, N, N-dibutylformamide, N-propyl-N-butyl- formamide, N, N-di-isobutyl-formamide and N-ethyl-N-cyclohexyl-formamide. These preferred compounds have a solubility in water of from about 0.5 to 10 foils, are liquids at the temperature at which coloring occurs, and are excellent solvents for dyes used in coloring human hair. The solvents are preferably contained in the colorants in a concentration of about 0.5 to 10%. If necessary, 2 or more solvents can be used in combination.

The invention further provides a method to: · dyeing human or animal hair, which is characterized by applying to the hair an effective Kenge for dyeing a dye and about 0.5 to 1 0 i> a formamide derivative of the formula

⁰ 'κ
H - C - N ^

R ₂

applies, where R -, - is a hydrogen atom, a lower one Alkyl radical, lower alkenyl radical or cycloalkyl radical or a hyaroxysubstituted lower alkyl radical, lower Alkenyl radical or cyeloalkyl radical and Rp a lower one Alkyl radical, lower alkenyl radical or cycloalkyl radical or a hydroxy-substituted lower alkyl radical, lower

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BATH

- 4 - ■ ■ mean alkenyl radical or cycloalkyl radical.

Dyes which can be used for dyeing from the solvent dyeing system with the formamides of the formula given above can be selected from various classes of dyes and should have a low solubility in water of 0.1 to 0.5 ° . The dyes that are suitable for dyeing include

(1) disperse dyes used for dyeing polyester fibers, Cellulose acetate and nylon can be used. They do not contain solubilizing groups like Sulfonic acid, carboxyl or quaternary nitrogen groups. You can go to the azo carbates and nitrodiphenylamine dyes or anthraquinone dyes !! belong. Examples of such dyes are:

Dispersion violet Dispersion violet Dispersion blue 1 Dispersion blue 3 Dispersion red 5 dispersion red 15 dispersion yellow 1 dispersion yellow 3 dispersion yellow 5

(2) Pre-metallized acidic dyes for neutral coloring. They are metal-containing azo dyes that act as metal Nickel, cobalt, iron or chromium contain the ratio of organic chelating compound to metal is 2: 1. They also have no solubilizing free sulfonic acid groups on.

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- 5 - ■
Examples of such dyes are:

Acid Red 213
Acid Yellow 217
Acid Black 58.

(3) Acid dyes, which have a sulfonic acid or contain carboxyl group, but very little in water due to the size of the molecule are soluble. Some of these dyes are also known as knuckle-fast acid dyes for wool. You insist mainly from bis- and trisazo dyes and dyes of the enthrachxnone group.

Examples of such dyes are:

Acid Blue 25
Acid blue 230
Acid blue 113
Acid Red 85
Acid Red 213
Acid yellow 27

(4) Another class of dyes which are suitable for the purposes of the invention are formed by the Nitro dyes, for example nitrophenols, nitro /

aminophenols, nitrophenylenediamines and derivatives thereof.

The pH of a hair dye can be from pH 3 to 9 »5 rich, optimal colorations are achieved with a pH value between 3 and 6. This is especially true when acidic dyes are used as the acid form of the dye is less soluble in water than you are Salt. The desired pH value can be achieved by adding acids or acidic salts or bases to the hair dye.

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BATH ORIGINAL

be asked. For example _, hydrochloric acid, sulfuric acid, formic acid, citric acid, tartaric acid, acetic acid or lactic acid, ammonium sulfate, ammonium chloride, triethanolamine, monoethanolamine, sodium carbonate, sodium hydroxide and borax are suitable for this purpose.

The hair dye can also contain the usual additives, for example thickeners, detergents, surface-active agents, gums and perfumes. However, a mixture of dye, solvent and water is sufficient to color the hair. As a thickening agent, carboxymethyl cellulose (CMC), hydroxyethyl cellulose (Cellosize), sodium alginate and the like can be used. Most ionic and nonionic detergents can be used in hair dyes. The amount of detergent can be 0.1 to 10 $, however, any increase in the amount of detergent in the hair dye will decrease the strength of the dye. Use can be made of this to adjust the strength of the coloring. Deeper shades are achieved with smaller amounts of detergent, ie 0.1 to 3 ^σ / ο, medium shades with 2 to 6 fo and light shades with 5 to 10 $ of a detergent or a mixture of detergents.

The ^ used close to dyes in a hair-coloring agent can vary depending on the desired color strength and the type of dye used 0.001 amounted to 2 fo. The percentages given above and elsewhere are based on weight.

The hair dyes according to the invention can be in the usual formulas as gels. Creams, pastes, solutions, Suspensions and dispersions are prepared. The processes for producing such agents are known. So can the desired amount of dye in the appropriate amount

909886/1520 BAD original

a solvent suitable for the purposes of the invention or a mixture of solvents. Water, thickeners and the like can be used on this Detergent or a mixture of detergents can be added. The pH can be adjusted at this point by adding Acid or base can be adjusted to the desired value. Then the perfume can be added.

Various other application methods can also be used can be used with success. So-you can use the dye or dissolve the dyes in the solvent and add water. This solution is applied to the hair. Then the hair is coated with a composition consisting of the thickener, detergent and water treated with any desired pH. Alternatively, the hair can be cleaned with an aqueous solution of the solvent Pre-treated and then with a dispersion of the dye in water containing the thickener, detergent and containing perfume, can be treated at any desired pH. Another way of applying is to the hair with a dispersion of the dye in water containing the thickener, detergent and perfume, to soak with a pH between 3 and 9.5 and then with an aqueous solution or dispersion of the solvent to treat.

For the application of the solution dyeing process is no special prepping of the hair required. So the hair dye can be on dry, damp or before washed hair can be applied.

The agents according to the invention can also be applied to untreated as applied to permed or bleached hair will.

9G2886 / 1520

BATH

0, 250 " 1, 000 P 40 3, 500 until pH 4.2 until 100

By, the following examples showing the manufacture of various show inventive agents, the invention is explained in more detail.

example 1

Weight - ° / o

Brillatizarin whale blue N, N-dibutyl-f-drmamide

Cellosize hydroxyethyl cellulose WP 4 0

Citric acid water

The agent is prepared according to the above approach and left untreated for a period of 20 minutes at room temperature gray and bleached human hair applied. The samples are rinsed, washed, and again flushed.

A bright deep blue will appear on both hair samples Preserved color.

example

Cellitone Fast Violet 6 BACF N, N-dibutylformamide Cellosize (HEC) WP Citric Acid

until Weight # 6 BACF until 0.250 1,000 40 3,500 pH 3 100

909886/1520

A hair dye is produced according to the above analysis and for a time of 10 minutes and 20 minutes at room temperature on untreated gray and bleached Human hair applied. The samples are rinsed, washed and rinsed again. On both hair samples A medium purple shade is achieved after 10 to 20 minutes of treatment.

Example 3

Weight

Irgalan Black 0.250

N, N-dibutylformamide 1,000

Cellosize hydroxyethyl cellulose WP 40 3.500

Citric acid up to pH 4.3

Water up to 100

Samples of untreated gray dry human hair and Pre-moistened, bleached human hair is treated with the above agent for 10 and 20 minutes. The robes are rinsed, washed and rinsed again.

A medium shade of gray is obtained on all hair samples after 10 or 20 minutes of treatment.

Example 4

Weight-5

Celliton blue GA extra 0.350.

N, N-pibutylformamide 1,000

polyethoxylated lanolin 0.300

Coconut alkanolamide 0.300

Cellosize hydroxyethyl cellulose WP 40 3.500

Triethanolamine up to pH 9.0

Water 'except for

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- ίο -

Samples of untreated and bleached human hair are treated with the above agent at room temperature for 20 minutes, rinsed, washed and again flushed.

A neutral shade of blue is obtained on all samples.

Example 5

Wt .- ^

Brillantalizarinwalk blue N-Cyclohexyl-formamide

Cellosize hydroxyethyl cellulose WP 40

Citric acid water

Samples of untreated hair and bleached hair can be used treated with the above agent at room temperature for 20 minutes, rinsed, washed and rinsed again.

A bright neutral shade of blue appears on both samples achieved.

Example 6

Weight- ^

Irgalan black BGL 0.250

N-cyclohexylformamide 5,500

Cellosize Hydroxyethyl Cellulose WP 40 3.200

Borax up to pH 7.3

Water 'up to 100

5, 250 3, VJl 2 until pH 4.1 until 100

909886/1520

Samples of dry and over-moistened untreated gray and bleached human hair are pre-. treated, rinsed, washed for 20 minutes and rinsed again.

A medium natural shade of gray will appear on the hair samples achieved.

Example 7

Weight -jo

Cellitone Fast Violet 6BA 0.250

N-butyl-N-propyl-formamide 3, 800

Cellosize HEC - WP 40 3.500

Citric acid up to pH 5 »6

Water up to 100

The above agent is prepared and stored at room temperature fanned out onto untreated gray and bleached human hair for a period of 20 minutes. The - ^ robes are rinsed, washed and rinsed again.

A deep purple hue is produced on both samples.

Example 8

Wt .- $

Real red B base. N-butyl-N-propyl-formamide Cellosize (HSG) WP 40 monoethanolamine water

0 on , 100 3 , 800 3 , 500 until pH 8.5 until 100

9 0 9 8 8 ■? / 1 -5 2 0

The above agent is prepared and stored at room temperature applied to samples of untreated gray and bleached human hair for a period of 20 minutes. The samples are rinsed, washed and rinsed again. ·

An illuminating deep yellow shade is produced.

For comparison, the same means are used as in the above examples, but without using the formamides. When such funds on hair samples are tested, they result in lower color yields and significantly poorer colorations.

0 9 8 8 5/1520

Claims (11)

Claims 1. Aqueous hair dye, g eke nnizei. without t through a for coloring effective amount of a dye and about 0.5 to 10 $ of a formamide derivative of the formula It H-C-N where IL is a hydrogen atom, a lower alkyl radical, lower alkenyl radical or cycloalkyl radical or a hydroxy-substituted lower alkyl radical, lower Alkenyl radical or cycloalkyl radical and R2 a lower alkyl radical, lower alkenyl radical or cycloalkyl radical or a hydroxy-substituted lower alkyl radical, lower alkenyl radical or cycloalkyl radical means. 2. Hair dye according to claim 1, characterized in that both of the formamide derivative used
Radicals R., and Rp mean butyl radicals or isobutyl radicals, 3. Hair dye according to claim 1, characterized in that in the formamide derivative used R ^ is a propyl radical and R _{2 is} a butyl radical. 4. Hair dye according to claim 1, characterized in that that in the formamide derivative R. used is a hydrogen atom and Rp is a cyclohexyl radical. 9 0 9 8 8 6/1520 5. Hair dye according to claim 1, characterized in that that in the formamide derivative used R.j is an ethyl radical and Rp is a cyclohexylreate. 6. Hair dye according to one of claims 1 to 5, characterized characterized in that the dye used is a disperse dye, a metallized azo dye for neutral dyeing, a millfast acid dye for wool or a nitro dye with a Water solubility is less than 0.5% by weight. 7. Hair dye according to one of claims 1 to 6, characterized characterized in that it contains one or more "thickeners, Contains detergents, surfactants, gums or perfumes. 8. Hair dye according to one of claims 1 to 7, characterized in that it has a pH value between 3 and 9.5, preferably between 3.5 and 6, has. 9. A method for dyeing human or animal hair, characterized in that one is on the hair for coloring effective amount of a dye and about 0.5 to 10 $ of a formamide derivative of the formula Il H-C-H brings up, in which R., a hydrogen atom, a lower one Alkyl radical, lower alkenyl radical or cycloalkyl radical or a hydroxy-substituted lower one Alkyl radical, lower alkenyl radical or cycloalkyl radical and R2 is a lower alkyl radical, lower alkenyl radical 909885 '1520 or Cycloarkyl radical or a hydroxy-substituted lower alkyl radical, lower alkenyl radical or cycloalkyl radical. · ^{R. r} 10. The method according to claim 9, characterized in that the agent is applied to the hair at a temperature below 40 ^° C., preferably at a temperature of about 20 to 25 ^° C. 11. Use of a formamide derivative of the formula H-C-N wherein R-. a hydrogen atom, a lower alkyl radical, lower alkenyl radical or cycloalkyl radical or a hydroxy-substituted lower alkyl radical, lower alkenyl radical or cycloalkyl radical and R ₂ denotes a n-mer alkyl radical, lower alkenyl radical or cycloalkyl radical or a hydroxy-substituted lower alkyl radical, lower alkenyl radical or cycloalkyl radical, as a solvent for a hair dye. 0 9886 ι λ 5? 0. L INSPECTED