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
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/35—Ketones, e.g. benzophenone
  • A61K8/355—Quinones
• • 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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
  • C07C225/24—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings
  • C07C225/26—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings
  • C07C225/32—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings of condensed quinone ring systems formed by at least three rings
  • C07C225/34—Amino anthraquinones
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
  • C09B1/16—Amino-anthraquinones
  • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
  • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
  • C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
  • C09B1/285—Dyes with no other substituents than the amino groups

Definitions

• the present invention relates to agents for dyeing hair containing 1,4-bis- [ " (dihydroxyalkyl) aminoj-anthraquinone and new 1,4-bis- (dihydroxyalkyl) aminoj-anthraquinones.
• dyes which are used for coloring human hair have to be harmless from a toxicological and dermatological point of view and enable coloring in the desired intensity. Furthermore, good light, permanent wave, Acid and rub fastness required. In any case, such hair coloring must remain stable over a period of at least 4 to 6 weeks without exposure to light, rubbing and chemical agents.
• the known 1,4-bis (2'-hydroxyethyl) amino-anthraquinone (Disperse Blue 23) has sufficient water solubility, but cannot be satisfactory in terms of the toxicological properties. For example, this dye shows a mutagenic effect in the Amestest.
• the object was therefore to provide hair colorants containing blue-coloring anthraquinone derivatives, the blue-coloring anthraquinone derivatives being said to have good water solubility in addition to good physiological compatibility.
• the new blue-coloring anthraquinone derivatives should enable more intense blue colorations than the previously known blue-coloring anthraquinones or their commercially available mixtures such as Celliton Fast Blue FFR®.
• R1 and R2 can be the same or different and independently of one another represent a straight-chain or branched C3- to C4-dihydroxyalkyl radical, the object is achieved in an outstanding manner.
• the compounds of the general formula (I) are notable for good physiological tolerance and very good absorbency on the hair.
• Hair dyeings carried out with the compounds of the general formula (I) are distinguished by a color-free shade of blue and have a significantly greater color intensity than hair dyeings which are customary with Disperse Blue 3, Disperse Blue 14 or Disperse Blue 23 or their used mixture, for example in the form of the commercial product Celliton Fast Blue FFR® (BASF AG, Ludwigshafen).
• the shading of hair colors by using a single defined dye of the general formula (I) is easier to carry out and therefore much more advantageous than the use of mixtures such as Celliton Fast Blue FFR® or the use of several dyes of the same color.
• the agents according to the invention the one which contains the 1,4-bis-j (2 ', 3'-dihydroxypropyl) amino-anthraquinone is preferred.
• the dyes of the general formula (I) should be present in the agent according to the invention in a concentration of 0.01 to 1.0 percent by weight, preferably in a concentration of 0.01 to 0.4 percent by weight.
• the hair coloring agent according to the invention relates both to an embodiment in which it is used without the addition of an oxidizing agent and to a further embodiment in which the addition of an oxidizing agent is required.
• the former hair dye without addition of oxidizing agent is an agent which contains at least one dye of the general formula (I), or an agent which, in addition to at least one dye of the general formula (I), also contains one or more others directly contains dyes on the hair.
• aromatic nitro dyes such as, for example, 2-amino-4-nitrophenol, 2-nitro-l, 4-diaminobenzene, 2-amino-5-nitrophenol, picraminic acid, 2-amino-5- (2'-hydroxyethyl) amino-nitrobenzene, 4- (2'-hydroxyethyl) amino-3-nitrophenol, 1- (2'-hydroxyethyl) amino-2-amino-4-nitrobenzene, 4- (2'-ureidoethyl) amino-nitrobenzene, 4- (2 ', 3'-dihydroxypropyl) amino-3-nitro-trifluoromethylbenzene, 1,4-bis-j (2'-hydroxyethyl, 2-amino-4-nitrophenol, 2-nitro-l, 4-di
• the dyes of the general formula (I) should be present in this hair dye without addition of oxidizing agents in a concentration of about 0.01 to 1.0 percent by weight, preferably in a concentration of 0.01 to 0.4 percent by weight.
• the total content of the dyes which are applied directly to the hair is in the range of about 0.01 to 3.0 percent by weight.
• the preparation of the hair dye described here without the addition of oxidizing agents can be, for example, that of a solution, in particular an aqueous or aqueous-alcoholic solution. Preferred forms of preparation are furthermore those of a cream, a gel, an emulsion or that of a foam, it also being possible to spray them in a mixture with a propellant gas or by means of a pump.
• the dyes of the general formula (I) should be present in this hair dye without adding any oxidizing agent in a concentration of about 0.01 to 1.0 percent by weight, preferably in a concentration of 0.01 to 0.4 percent by weight.
• the total content of the dyes which are applied directly to the hair is in the range of about 0.01 to 3.0 percent by weight.
• the pH of this colorant is in the range from 3 to 10.5, in particular at pH 7.5 to 9.5, the desired alkaline pH being set primarily with ammonia, but also with organic amines such as, for example, monoethanolamine or Triethanolamine can be made.
• the use of the hair dye described here without the addition of an oxidizing agent is usually carried out by applying to the hair an amount sufficient for hair dyeing with which it remains in contact for about 5 to 30 minutes. It is then rinsed with water, if appropriate also with an aqueous solution of a weak organic acid, and dried.
• a weak organic acid for example, acetic acid, citric acid, tartaric acid and the like can be used as the weak organic acid.
• the hair dye described above without the addition of an oxidizing agent can be in the form of a hair dye with additional hair fixation, which contains at least one polymer or natural polymer that is commonly used in cosmetics. Such agents are generally referred to as tinting or color strengthening agents.
• polymers known for this purpose in cosmetics are, for example, polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol or polyacrylic compounds such as polyacrylic acid or polymethacrylic acid, basic polymers of the esters of polyacrylic acid or polymethracrylic acid with amino alcohols or their salts or quaternization products, polyacrylonitrile, Polyvinyl lactams and copolymers of these compounds, such as polyvinylpyrrolidone-vinyl acetate and the like, are mentioned.
• Natural polymers such as chitosan (deacetylated chitin) or chitosan derivatives, can also be used for the purpose mentioned.
• the polymers and natural polymers are contained in the hair colorant described above without any oxidizing agent in the amount of about 1 to 5 percent by weight customary for such agents.
• the pH of the agent is in the range of about 6.0 to 9.0.
• This 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 can, if required, without the addition of an oxidizing agent, further additives which are customary for hair coloring agents, such as, for example, care substances, wetting agents, thickeners, plasticizers, preservatives and perfume oils, and also other customary additives listed below for hair coloring agents with addition of an oxidizing agent (oxidizing hair dye) Additives included.
• the subject matter of the present invention also includes a hair colorant in which the addition of an oxidizing agent is necessary (oxidation hair colorant).
• it additionally contains at least one developer substance-coupler substance combination which requires oxidative development.
• the oxidation hair dye according to the invention can contain at least one dye which is applied directly to the hair and which should be selected from: 2-amino-4-nitrophenol, 2-nitro-l, 4-diamino-benzene, 2-amino-5-nitrophenol, 2- Amino-4,6-dinitrophenol, 2-amino-5- (2'-hydroxyethyl) amino-3-nitrobenzene, 4- (2'-hydroxyethyl) amino-3-nitrotoluene, 4- (2'-ureido-ethyl) amino-nitrobenzene, Basic Violet 14 (CI 42 510), Basic Violet 2 (CI 42 520), Acid Brown 4 (CI 14 805), 1,4-diaminoanthraquinone and 1,4,5,8-tetra-aminoanthraquinone.
• 2-amino-4-nitrophenol 2-nitro-l
• 4-diamino-benzene 2-amino-5-nitrophenol
• 2- Amino-4,6-dinitrophenol 2-a
• the oxidation hair dye according to the invention can also contain self-coupling dye precursors, such as 2-amino-5-methylphenol and 6-amino-2-methylphenol.
• aromatic p-diamines and p-aminophenols such as 1,4-diamino benzene, 2,5-diaminotoluene, 2,5-diaminobenzyl alcohol, 2- (2'- Hydroxyethyl) -1,4-diaminobenzene, 4-aminophenol, 4-amino-3-methylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-ethoxymethylphenol and tetraaminopyrimidine or similar compounds.
• aromatic p-diamines and p-aminophenols such as 1,4-diamino benzene, 2,5-diaminotoluene, 2,5-diaminobenzyl alcohol, 2- (2'- Hydroxyethyl) -1,4-diaminobenzene, 4-aminophenol, 4-amino-3-methylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-
• the oxidation hair dye according to the invention should contain the developer and coupler substances in an amount of 0.01 to 5 percent by weight, preferably in an amount of 0.1 to 3 percent by weight.
• the coupler and developer substances mentioned can in each case be present individually or in a mixture with one another in the hair colorants according to the invention.
• the developer substances are generally used in approximately equimolar amounts, based on the coupler substances. However, it is not a disadvantage if the developer substance is present in a certain excess or deficit in this regard.
• the coupler and developer substances as well as the other color components can also be used in the form of the physiologically compatible acid addition salts, such as, for example, as hydrochloride or sulfate or - if they have aromatic hydroxyl groups - in the form of the salts with bases, for example as alkali phenolates.
• physiologically compatible acid addition salts such as, for example, as hydrochloride or sulfate or - if they have aromatic hydroxyl groups - in the form of the salts with bases, for example as alkali phenolates.
• the total amount of the developer substance-coupler substance combination contained in the oxidation hair colorant described here should be about 0.1 to 5.0 percent by weight, preferably 0.5 to 4.0 percent by weight.
• the dyes of the general formula (I) should be present in the oxidation hair dye described above in a concentration of 0.01 to 1.0 percent by weight, preferably in a concentration of 0.01 to 0.4 percent by weight.
• the cosmetic hair dye can also contain other cosmetic additives, for example antioxidants such as ascorbic acid, thioglycolic acid or sodium sulfite, perfume oils, complexing agents, wetting agents, emulsifiers, thickeners, care agents and others.
• the oxidation hair colorants according to the invention can react weakly acidic, neutral or alkaline.
• they have a pH in the alkaline range between 8.0 and 11.5, the setting preferably being made with ammonia.
• organic amines for example monoethanolamine and triethanolamine, or else inorganic bases such as sodium hydroxide and potassium hydroxide can also be used.
• the main oxidizing agents used to develop hair color are hydrogen peroxide and its addition compounds to urea, melanin or sodium borate in the form of 3 to 12%, preferably 6%, aqueous solutions.
• the weight ratio between the hair dye and the oxidizing agent is 5: 1 to 1: 2, but preferably 1: 1. Larger amounts of oxidizing agent are used above all in the case of higher dye concentrations in the hair dye or when more bleaching of the hair is intended at the same time.
• the form of preparation of the oxidizing hair dye can be the same as that of the previously described hair dye without the addition of an oxidizing agent, for example that of an aqueous or aqueous-alcoholic solution.
• the preparation form is preferably that of a cream, a gel or that of an emulsion.
• Usual additives in solutions, creams, emulsions or gels are, for example, solvents such as water, lower aliphatic alcohols, for example ethanol, propanol and isopropanol or glycols such as glycerol and 1,2-propylene glycol, furthermore wetting agents or emulsifiers from the classes of the anionic, cationic, amphoteric or nonionic surfactants such as fatty alcohol sulfates, ethoxylated fatty alcohol sulfates, alkylsulfonates, alkylbenzenesulfonates, alkyltrimethylammonium salts, alkylbetaines, oxyethylated fatty alcohols, oxyethylated nonylphenols, fatty acid alkanolamides, ethoxylated fatty acid ester, further Ver ⁇ thicker such as higher fatty alcohols, starch or cellulose derivatives, petroleum jelly, paraffin oil and fatty acids as well as
• the components 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 a concentration of about 0.1 to 5.0 weight percent.
• the oxidizing hair dye described above is mixed with an oxidizing agent immediately before use and an amount sufficient for the hair dyeing treatment, depending on the fullness of the hair, is generally about 60 to 200 g of this mixture on the hair.
• the mixture is allowed to act on the hair at 15 to 50 ° C for about 10 to 45 minutes, preferably 30 minutes, then the hair is rinsed with water and dried. If necessary, this rinse is washed with a shampoo and possibly rinsed with a weak organic acid, such as citric acid or tartaric acid. The hair is then dried.
• a weak organic acid such as citric acid or tartaric acid.
• oxidation hair colorants according to the invention containing at least one 1,4-bis- (dihydroxyalkyl) amino] anthraquinone of the general formula (I) lead to hair colorations with excellent fastness properties and high color intensity, never in the hair colorants described here and compounds of the formula (I) which do not contain any oxidizing agent are toxicologically and dermatologically harmless, readily water-soluble and stain alone in a clear shade of blue.
• the compounds of the general formula (I) are particularly suitable for shading intense black shades.
• This application also relates to the 1,4-bis j (dihydroxyalkyl) amino] anthraquinone of the general formula (II)
• R1 and R2 can be the same or different and independently of one another represent a straight-chain or branched C3- to C4-dihydroxyalkyl radical.
• An example of the new 1,4-bis- (dihydroxyalkyl) aminoj -anthraquinones of the general formula (II) is 1,4-bis- (2 ', 3'-dihydroxypropyl) amino J-anthraquinone.
• the new 1,4-bis- ((dihydroxyalkyl) aminoj-anthraquinones can be described according to, for example, in the textbook NN Woroshzow, Basics of the Synthesis of Intermediates and Dyes, Akademie Verlag, Berlin (1966), pages 481-482 to produce the described process, in which the industrially available 1,4-dihydroxyanthraquinone is first reduced to 1,4,5,8-tetrahydroanthraquinone in a alkaline aqueous solution using a conventional reducing agent, for example sodium dithionite
• a conventional reducing agent for example sodium dithionite
• the 1,4,5,8-tetrahydroanthraquinone is then treated under a protective gas atmosphere, for example under nitrogen, with a implemented aqueous solution of the corresponding amino-alkyldiol in the heat.
• Oxygen is then passed into the reaction mixture to reoxidize the quinone system, causing the 1,4-bis- (d
• the compounds of the general formula (II) are intensely blue-coloring anthraquinone dyes which, in addition to good water solubility, are also notable for their good physiological tolerance. Because of their properties, the compounds of the formula (II) are valuable blue-coloring hair dyes.
• 1,4-dihydroxyanthraquinone 50 g are dissolved in 1,000 ml of 5 percent sodium hydroxide solution and reduced with 500 ml of 20 percent sodium dithionite solution. After slower 75.8 g of 3-aminopropane-1,2-diol in 30 ml of water are added and the mixture is heated to 100 ° C. under nitrogen for 8 hours. Then oxygen is introduced for 3 hours. The 1,4-bis ((2 ', 3'-dihydroxypropyl) aminoj-anthraquinone is then filtered off and washed with acetone. 38 g of deep blue crystals, corresponding to a yield of 47% of theory, with a decomposition melting point of 220 ° C obtained.
• Bleached natural hair is treated with the above liquid hair dye at room temperature for 20 minutes. After rinsing the hair with water and then drying it, the hair is colored in a blonde-ash color.
• Lauryl alcohol diglycol ether sulfate sodium salt 28 percent aqueous solution of methyl p-hydroxybenzoate ammonia, 25 percent aqueous solution of water
• Example C Color fastener
• White human hair is inserted with the color fixer solution and dried.
• the hair is colored and set in a fashionable silver tone.
• 50 g of the above oxidation hair dye in gel form are mixed with 50 g of a 6% hydrogen peroxide solution and applied to white human hair. After an exposure time of 30 minutes at 40 degrees Celsius, the hair is rinsed with water, if necessary shampooed and dried. The hair is dyed in a natural medium blonde shade with a slight ash effect.

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• Chemical & Material Sciences (AREA)
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Citations (4)

• 1990
  • 1990-10-15 DE DE19904032607 patent/DE4032607A1/de not_active Withdrawn
• 1991
  • 1991-09-26 ES ES91916571T patent/ES2042469T1/es active Pending
  • 1991-09-26 EP EP19910916571 patent/EP0505528A1/de not_active Withdrawn
  • 1991-09-26 WO PCT/EP1991/001836 patent/WO1992006670A1/de not_active Application Discontinuation

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