Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/41—Amines
  • A61K8/418—Amines containing nitro groups
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
  • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/10—Preparations for permanently dyeing the hair

Definitions

• the invention relates to an agent for dyeing fibers, in particular keratinic fibers, containing nitrophenylamines and a method for dyeing hair using this agent.
• Nitro dyes have become particularly important for hair coloring. They are an important component in oxidation hair dyes to round off the color result and to create fashionable color shades. By combining yellow, red and blue nitro dyes, it is also possible to produce dyes that are able to dye hair in natural to fashionable shades without the addition of oxidizing agents.
• nitro dyes which color the hair in an intense lemon yellow, which should be as free of red as possible.
• nitro dyes still have to meet a whole series of additional requirements. So they have to be harmless from a toxicological and dermatological point of view and enable the dyeing to be achieved in the desired intensity, which among other things also requires sufficient water solubility.
• good lightfastness, rubbing fastness, perming fastness and perspiration fastness are required for the dyeings obtained.
• the dyes must not be washed out too easily during post-treatment or shampooing. Their use in oxidation hair colorants further presupposes that they are stable in the presence of reducing agents and oxidizing agents, especially in alkaline solution.
• the present invention therefore relates to agents for dyeing fibers, in particular keratin fibers, such as human hair, which are characterized in that they contain at least one compound of the formula (I),
• R1 is hydrogen or a straight-chain or branched-chain
• Y is a heterocyclic ring of formula (II)
• the compounds of the general formula (I) are preferably selected from N- (2-methoxyethyl) -4-nitro-phenylamine, N- (2-methoxyethyl) -2-methyl-4-nitro-phenylamine, 4- (4-nitro -phenyl) - morpholine, N- (3-methoxypropyl) -4-nitro-phenylamine, N- (3-methoxypropyl) - 2-methyl-4-nitro-phenylamine, 4- (2-methyl-4-nitro-phenyl ) -morpholine, N-cyclopropyl-4-nitro-phenylamine, 4-nitro-N - ((tetrahydrofuran-2-yl) methyl) - phenylamine, 2-methyl-4-nitro-N- (tetrahydrofuran-2-yl- methyl) phenylamine and N-cyclopropyl-2-methyl-4-nitro-phenylamine.
• the dyes of the formula (I) are preferably used in the colorants according to the invention in a total amount of 0.01 to 10 percent by weight, in particular in a total amount of 0.1 to 5 percent by weight.
• the dyes of the formula (I) can be easily prepared from available precursors and not only have good water solubility, but also very good absorption behavior from anionic, cationic, amphoteric or nonionic carrier compositions.
• the dyeings obtained have a high resistance to washing out, sweat and light radiation and to bases such as ammonia and acids such as phosphoric acid, or reducing agents such as ascorbic acid or sodium sulfite, whereby the use in oxidative colorants is considerably facilitated.
• the colorants according to the invention also have a high storage stability and enable intensely bright yellow shades, with possible variations in all shades and shades from a light lemon yellow to an intense dark yellow.
• the colorants according to the invention can be used either without or with the addition of an oxidizing agent, in which case customary developer substances and coupler substances are added.
• the colorant can also contain, in addition to the dyes of the formula (I), other known direct-coloring dyes from the group consisting of nitro dyes, azo dyes, anthraquinone dyes and triphenylmethane dyes, alone or in a mixture with one another.
• other known direct-coloring dyes from the group consisting of nitro dyes, azo dyes, anthraquinone dyes and triphenylmethane dyes, alone or in a mixture with one another.
• Suitable substantive dyes are 1,4-bis [(2-hydroxyethyl) amino] -2-nitrobenzene, 1- (2-hydroxyethyl) amino-2-nitro-4- [di (2-hydroxyethyl) amino] benzene (HC Blue No. 2), 1-amino-3-methyl-4 - [(2-hydroxyethyl) amino] -6-nitrobenzene (HC Violet No. 1), 4- [ethyl- (2-hydroxyethyl) amino] -1 - [(2-hydroxyethyl) amino] -2-nitrobenzene hydrochloride (HC Blue No.
• the above-mentioned direct nitro dyes, azo dyes, anthraquinone dyes or triphenylmethane dyes can be contained in a total amount of about 0.01 to 4 percent by weight, the total content of non-oxidative dyes preferably being about 0.01 to 8 percent by weight, in particular 0.1 to 5 percent by weight , is.
• the preparation form of the colorant according to the invention based on compounds of the general formula (I) and, if appropriate, direct-coloring dyes can be, for example, a solution, in particular an aqueous-alcoholic solution.
• Preferred forms of preparation are also creams, gels or emulsions. It is also possible to take these agents out of a pressure container with the aid of an atomizer or other suitable pump devices or spray devices or in a mixture with conventional propellants liquefied under pressure as an aerosol spray or aerosol foam.
• the pH of this colorant is in the range from 3 to 12, in particular at a pH from 8 to 11, 5, the desired alkaline pH being set preferably with ammonia, but also with organic amines such as, for example, monoethanolamine or Triethanolamine can be made, while diluted organic or inorganic acids, such as hydrochloric acid, sulfuric acid, phosphoric acid, ascorbic acid or lactic acid, are used for the adjustment of an acidic pH depending on the desired pH.
• This dye is used for hair dyeing in a customary manner by applying a sufficient amount of the dye to the hair with which it remains in contact for a period of time, preferably 15 to 30 minutes.
• the hair is then rinsed with water and then, if appropriate, with an aqueous solution of a weak organic acid and then dried.
• a weak organic acid for example, acetic acid, citric acid or tartaric acid in the form of a dilute aqueous solution can be used as the weak organic acid.
• the colorant described above without the addition of oxidizing agents can furthermore contain natural or synthetic polymers or modified polymers of natural origin which are customary for cosmetic products, as a result of which hair is set at the same time as the coloring.
• Such agents are generally referred to as tinting or color strengthening agents.
• polyvinyl pyrrolidone polyvinyl acetate, polyvinyl alcohol or polyacrylic compounds such as polyacrylic acid or polymethacrylic acid, basic polymers of esters of polyacrylic acid, polymethylacrylic acid and amino alcohols, for example their salts or quaternization products, polyacrylonitrile, polyvinyl acetate and copolymer Compounds such as polyvinyl pyrrolidone vinyl acetate mentioned; while natural polymers or modified natural polymers, for example chitosan (deacetylated chitin) or chitosan derivatives, can be used.
• the abovementioned polymers can be present in the agent according to the invention in the amounts customary for such agents, in particular in an amount of about 1 to 5 percent by weight.
• the pH value of the tinting or color fixing agent according to the invention is about 6 to 9.
• the hair dye with additional setting is used in a known and customary manner by moistening the hair with the setting agent, setting (inserting) the hair for the hairstyle and subsequent drying.
• the hair colorant described above may optionally contain further additives customary for hair colorants, such as, for example, care substances, wetting agents, thickeners, plasticizers, preservatives and perfume oils, and also other customary additives listed below for oxidation hair colorants.
• further additives customary for hair colorants such as, for example, care substances, wetting agents, thickeners, plasticizers, preservatives and perfume oils, and also other customary additives listed below for oxidation hair colorants.
• the subject of the present invention also includes hair colorants in which the addition of an oxidizing agent is required.
• an oxidizing agent is required.
• these colorants additionally contain known oxidation dye precursors which require oxidative treatment (developer substances and Coupler substances).
• developers are 1,4-diamino-benzene (p-phenylenediamine), 1,4-diamino-2-methyl-benzene (p-toluenediamine), 1,4-diamino-2,6-dimethyl-benzene, 1,4 4-diamino-2,5-dimethyl-benzene, 1, 4-diamino-2,3-dimethyl-benzene, 2-chloro-1, 4-diaminobenzene, 4-phenylamino-aniline, 4-dimethylamino-aniline, 4- Diethylamino aniline, 4- [di (2-hydroxyethyl) amino] aniline, 4 - [(2-methoxyethyl) amino] aniline, 4 - [(3-hydroxypropyl) amino] aniline, 1,4-diamino 2- (2-hydroxyethyl) benzene, 1,4-diamino-2- (1-methylethyl) benzene,
• couplers are 5 - ((2-hydroxyethyl) amino) -2-methoxyaniline, N- (3-dimethylaminophenyl) urea, 2,6-diamino-pyridine, 2-amino-4 - [(2-hydroxyethyl ) amino] anisole, 2,4-diamino-1-fluoro-5-methyl-benzene, 2,4-diamino-1-methoxy-5-methyl-benzene, 2,4-diamino-1-ethoxy-5- methyl-benzene, 2,4-diamino-1- (2-hydroxyethoxy) -5-methyl-benzene, 2,4-di [(2-hydroxyethyl) amino] -1, 5-dimethoxy-benzene, 2,3- Diamino-6-methoxy-pyridine, 3-amino-6-methoxy-2- (methylamino) pyridine, 2,6-diamino-3,5- dimethoxy-pyridine
• Especially preferred compounds are 1,4-diamino-2-methylbenzene, 4- [di (2-hydroxyethyl) amino] aniline, 1,4-diamino-2- (2-hydroxyethyl) benzene, 4 -Amino-3-methylphenol, 4-amino-2- (aminomethyl) phenol, 2,4,5,6-tetraamino-pyhmidine, 4,5-diamino-1- (2-hydroxy-ethyl) -1 H- Pyrazole, 4-chlororesorcinol, 3-aminophenol, 5-hydroxy-1, 3-benzodioxole, 5-amino-1, 3-benzodioxole, 5 - ((2'-hydroxyethyl) amino) -1, 3-benzodioxole, 2 - Amino-4 - [(2-hydroxyethyl) amino] anisole, 2,4-diamino-1-fluoro-5-methylbenzene, 5-amino-2-
• Combinations of oxidation dyes and the dyes of formula (I) can be used to produce natural shades of blonde and brown, but also fashionable shades.
• the dyes of the formula (I) according to the invention are preferably present in the colorant with the addition of oxidizing agent in an amount of about 0.01 to 4.0 percent by weight, in particular 0.02 to 2.0 percent by weight, the total content of non-oxidative Dyes are preferably about 0.1 to 5 weight percent.
• the total concentration of oxidation dye precursors in the oxidation colorant according to the invention is approximately 0.1 and 10 percent by weight, an amount of 0.2 to 2 percent by weight being preferred.
• the desired alkaline pH is usually set with ammonia; however, other organic amines, for example monoethanolamine or triethanolamine, or inorganic bases such as sodium hydroxide and potassium hydroxide can be used while adjusting an acidic pH with organic acids such as citric acid, glycolic acid, lactic acid, malic acid, ascorbic acid or tartaric acid , he follows.
• Hydrogen peroxide and its addition compounds are primarily considered as oxidizing agents for developing the color.
• the form of preparation of the oxidation colorant according to the invention can be the same as that of the non-oxidative colorant according to the invention, the oxidation colorant preferably being in the form of a cream or a gel.
• Usual additives in solutions, creams, emulsions or gels are, for example, solvents such as water, lower aliphatic monohydric or polyhydric alcohols, their esters and ethers, for example alkanols, in particular with 1 to 4 carbon atoms, for example ethanol, propanol or isopropanol, butanol, Isobutanol, dihydric and trihydric alcohols, especially those with 2 to 6 carbon atoms, for example ethylene glycol, propylene glycol, 1, 3-propanediol, 1, 4-butanediol, 1, 5-pentanediol, 1, 6-hexanediol, 1, 2, 6-hexanetriol, glycerol, diethylene glycol, dipropylene glycol, polyalkylene glycols, such as triethylene glycol, polyethylene glycol, tripropylene glycol, polypropylene glycol, lower alkyl ethers of polyhydric alcohols, such as
• wetting agents or emulsifiers from the classes of the anionic, cationic, amphoteric, non-ionic or zwitterionic surface-active substances such as fatty alcohol sulfates, alkane sulfonates, alkylbenzenesulfonates, alkyltrimethylammonium salts, alkylbetaines, ⁇ -olefin sulfonates, ethoxylated fatty alcohols, ethoxylated nonylphenols, fatty acid alkanolamines, ethoxylated fatty acid glycols, fatty alcohol alcoholates, fatty alcohol alcoholates, fatty alcohol alcoholates, fatty alcohol alcoholates, fatty alcohol alcoholates, fatty alcohol alcoholates, fatty alcohol alcohols, fatty alcohol alcohols, fatty alcohol alcoholates, fatty alcohol alcohols, fatty alcohol alcohols, fatty alcohol alcohols, fatty alcohol alcoholates, fatty alcohol alcohols, fatty alcohol alcohols, fatty alcohol alcohols, fatty alcohol alcohols,
• ingredients mentioned are used in the amounts customary for such purposes, for example the wetting agents and emulsifiers in concentrations of about 0.5 to 30 percent by weight, the thickeners in an amount of about 0.1 to 25 percent by weight and the care substances in an amount of about 0.1 to 5 weight percent.
• the colorant described above is mixed immediately before use with an oxidizing agent and applies a sufficient amount for the hair dye treatment, depending on the fullness of the hair, generally about 60 to 200 g, of this mixture to the hair.
• the main oxidizing agents used to develop hair color are hydrogen peroxide or its addition compounds with urea, melanin or sodium borate in the form of 3 to 12%, preferably 6%, aqueous solutions.
• the weight ratio between coloring agent and oxidizing agent is 5: 1 to 1: 2, but preferably 1: 1. Larger amounts of oxidizing agent are used above all at higher dye concentrations in the coloring agent or when more bleaching of the hair is intended at the same time.
• the dyeing solution is allowed to act on the hair at 20 to 50 ° C. for about 10 to 45 minutes, preferably 40 ° C. for 40 minutes, the hair is then rinsed out with water and dried. If necessary, this is rinsed with a shampoo and rinsed. The hair is then dried.
• the dye according to the invention leads - especially in the case of hair dyeing - to dyeings with excellent fastness properties, in particular as regards light fastness, wash fastness and perspiration fastness.
• the high color intensity and the color purity of the dyeings that can be achieved are remarkable even after three months of storage.
• the colorant described there is also no graying or chemical staining pre-damaged hair is possible without problems and with good coverage.
• the dyeings obtained are uniform and very reproducible, regardless of the different structure of the hair.
• the hair colorants are used either in conjunction with or without an oxidizing agent.
• the colorants according to the invention based on compounds of the formula (I) are particularly suitable for coloring keratin fibers, such as wool, furs or hair, in particular human hair;
• these colorants it is also readily possible to use these colorants to use other natural fibers such as cotton, jute, sisal, linen or silk, modified natural fibers such as regenerated cellulose, nitrocellulose, alkyl cellulose, hydroxyalkyl cellulose or acetyl cellulose, or synthetic fibers such as for example polyamide fibers, polyurethane fibers and polyester fibers.
• the above color carrier is mixed into the ready-to-use hair dye immediately before use.
• An intensive lemon-yellow color results after both acidic and basic treatment. The color obtained survives up to five washes or a three-week exposure to sunlight without a noticeable loss in intensity.
• the ready-to-use hair dye is made just before use by mixing the other ingredients with water.
• Example 13 Hair dye with N- (3-methoxypropyl) -4-nitro-phenylamine
• the ready-to-use hair dye is made just before use by mixing the other ingredients with water.
• a dark yellow color results after both acidic and basic treatment.
• the color obtained lasts up to five washes or a three-week exposure to sunlight without a noticeable loss in intensity.
• Example 15 Hair dye with N- (3-methoxypropyl) -2-methyl-4-nitrophenylamine
• the ready-to-use hair dye is made just before use by mixing the other ingredients with water.
• the ready-to-use dye is used immediately before use
• Hair or wool or cotton are then each 40 minutes at a temperature of 40 ° C with the two colorants
• the result is a yolk color.
• the color obtained survives up to five Washing or a three-week exposure to sunlight without a noticeable loss in intensity.
• the ready-to-use hair dye is made just before use by mixing the other ingredients with water.
• Example 18 Colorant with 4-nitro-N - ((tetrahydrofuran-2-yl) methyl) phenylamine
• the ready-to-use colorant is produced immediately before use by mixing the remaining ingredients with water.
• the fibers are then rinsed with water and dried. An intense dark yellow coloration results after both acidic and basic treatment. The color obtained survives up to five washes or a three-week exposure to sunlight without a noticeable loss in intensity.
• a mustard yellow color results after both acidic and basic treatment.
• the color obtained lasts up to five washes or a three-week exposure to sunlight without a noticeable loss in intensity.
• 50 g of the above hair dye are mixed with 50 g of hydrogen peroxide solution (6% strength aqueous solution) immediately before use and applied to bleached hair. After an exposure time of 30 minutes, the hair is rinsed with water, shampooed and dried. The hair gets a brown color.
• hydrogen peroxide solution 6% strength aqueous solution
• 50 g of the above hair dye are mixed with 50 g of hydrogen peroxide solution (6% strength aqueous solution) immediately before use and applied to bleached hair. After an exposure time of 30 minutes, the hair is rinsed with water, shampooed and dried. The hair treated in this way receives a natural light brown color
• 50 g of the above hair dye are mixed with 50 g of hydrogen peroxide solution (6% strength aqueous solution) immediately before use and applied to bleached hair. After an exposure time of 30 minutes, the hair is rinsed with water, shampooed and dried. A brown color is obtained.
• hydrogen peroxide solution 6% strength aqueous solution
• 50 g of the above hair dye are mixed with 50 g of hydrogen peroxide solution (6% strength aqueous solution) immediately before use and applied to bleached hair. After an exposure time of 30 minutes, the hair is rinsed with water, shampooed and dried. The hair is dyed in an intense shade of brown.
• hydrogen peroxide solution 6% strength aqueous solution
• the above color carrier is mixed into the ready-to-use hair dye immediately before use.
• Bleached hair is then treated for 40 minutes at a temperature of 40 ° C with the hair dye (once acidic and once basic).
• the hair is then rinsed with water and dried. The hair treated in this way gets a dark brown color.
• the pH is adjusted a) with lactic acid or b) with dilute ammonia solution.
• the fibers are then rinsed with water and dried.
• the color measurement values of 5 colored strands of hair are determined.
• the strands of hair are then shampooed 5 times in succession with a neutral shampoo for 1 minute, then rinsed with water and dried. Following this treatment, the color measurement values of the individual strands are determined again and the difference between the color measurement values before and after the treatment is determined.
• the mean of the results of the 5 strands of hair is listed in Table 1.
• the color measurement values of 5 colored strands of hair are determined. Then the strands of hair are each in the solution of synthetic sweat from 10.00 g of sodium chloride 1.00 g of di-potassium phosphate 0.25 g of DL-histidine ad pH 3.2 lactic acid listed below immersed in 100.00 g of water and left twice in this solution for 24 hours at 37 ° C.
• the strands of hair are then rinsed out with water and dried.
• the color measurement values of the individual strands are determined again and the difference between the color measurement values before and after the treatment is determined.
• the color measurement values of 5 colored strands of hair are determined.
• the dyed strands of hair are then irradiated with a rapid exposure device of the "Atlas Suntest CPS +" brand, with a xenon arc discharge lamp 1.5 kW.
• the light fastness is assessed by comparing the change in the color measurement values with that of the type colorations of the light fastness scale.
• the color measurement values of the individual strands are determined again and the difference between the color measurement values before and after the treatment is determined.
• the L * a * b * color measurement values given in Table 1 below were determined using a color measurement device from Minolta, type Chromameter II.
• the total color differences ( ⁇ E color measurement values) are given in accordance with the CIE color system L * a * b *.
• the L value stands for the Brightness (the lower the L-value, the darker the sample and the higher the L-value, the brighter the sample), while the a-value is a measure of the red or green part (the larger or more positive the a- Value is the greater the red component and the smaller or more negative the a value is, the larger the green component).
• the b value is a measure of the blue component or yellow component (the larger or more positive the b value is, the larger the yellow component and the smaller or more negative the b value is, the greater the blue component).
• the ⁇ E value is a measure of the color change, the greater the ⁇ E value, the greater the loss in intensity of the coloring.
• the hair colorants according to the invention (Examples 1 + 2) have a higher stability of the dyeings with respect to washing out and the influence of sweat and light radiation than a conventional hair colorant.

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• 1998
  • 1998-10-13 DE DE19847192A patent/DE19847192A1/de not_active Withdrawn
• 1999
  • 1999-09-08 AT AT99944624T patent/ATE258782T1/de not_active IP Right Cessation
  • 1999-09-08 JP JP2000575472A patent/JP2002527369A/ja active Pending
  • 1999-09-08 US US09/581,367 patent/US6379400B1/en not_active Expired - Lifetime
  • 1999-09-08 EP EP99944624A patent/EP1037593B1/de not_active Expired - Lifetime
  • 1999-09-08 BR BR9906871-0A patent/BR9906871A/pt not_active Application Discontinuation
  • 1999-09-08 ES ES99944624T patent/ES2214882T3/es not_active Expired - Lifetime
  • 1999-09-08 DE DE59908466T patent/DE59908466D1/de not_active Expired - Lifetime
  • 1999-09-08 WO PCT/EP1999/006601 patent/WO2000021496A1/de not_active Ceased

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