US3194734A - Processes and compositions for dyeing hair and similar fibres - Google Patents

Processes and compositions for dyeing hair and similar fibres Download PDF

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Publication number
US3194734A
US3194734A US126749A US12674961A US3194734A US 3194734 A US3194734 A US 3194734A US 126749 A US126749 A US 126749A US 12674961 A US12674961 A US 12674961A US 3194734 A US3194734 A US 3194734A
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solution
hair
indole
dihydroxy
water
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Seemuller John Robert
Pigerol Charles
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LOreal SA
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LOreal SA
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/30—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts
    • D06P3/305—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts with oxidation dyes
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
    • 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

  • This invention is also an improvement over U.S. Patent No. 2,934,296, which discloses a process for tinting hair and other keratinous materials, using dihydroxy-5,6-indole in an acid solution, which is applied to the hair and then oxidized in order to fix the dihydroxy-5,6-indole.
  • dihydroxyphenylalanine may be converted to a brown pigment by certain enzymes, such conversion taking place over a long period of time. This process is so slow that it is unsuitable for dyeing live human hair.
  • the dihydroxy-5,6-indole normally produces a black or deep brown color, and when it is desired to obtain a lighter color, it is necessary to destroy by oxidation a portion of the pigments after they have been formed, thus lightening the color produced by the re mainder of the pigments. This destruction, which has a bleaching effect, takes place simultaneously with the dyeing.
  • Another disadvantage is the impossibility of knowing :the exact moment at which the formation of pigments stops and the bleaching, that is to say, the partial destruction of the pigment starts.
  • a process for dyeing human hair and other keratinous fibers comprises applying thereto an aqueous alkaline composition containing dihydroxy-5,6-indole and ammonia, an ammonium salt or an amine, allowing the hair or other keratinous fiber to remain in contact with the said composition until the desired shade is obtained and then rinsing the hair free of such composition.
  • Another object of this invention is to produce a hair dye, which contains at least one ingredient having the following general formula:
  • the said methyl derivatives of dihydroxy-5,6-indole are prepared in an aqueous solution or in the form of a cream.
  • aqueous solution herein designates any solution, the principal solvent of which is water. These solutions may comprise other solvents miscible in water, such as ethyil alcohol, isopropyl alcohol, glycols, esters of glycol, etc.
  • the invention also relates to a process for the dyeing of hair which is characterized by the fact that the hair is impregnated with a solution or a cream containing at least one derivative of dihydroxy-5,6-indole having the following formula:
  • R, R R designate hydrogen or a methyl radical, at least one of the three radicals R, R and R being other than hydrogen, and in which the color is developed by an oxidizing agent.
  • concentrations of the said methyl derivative of dihydroxy-5, 6-indole, which are applied to the hair may vary within broad limits, but falls generally between 0.2% and 6% by weight of the solution and falls preferably between 0.5% and 3%.
  • Particularly suitable oxidizing agents include: hydrogen peroxide, odium brom-ate, sodium percarbonate, sodium persulf-ate, ammonium persulfate, etc.
  • This invention is directed to a new hair dye and to hair dyed with this new dye.
  • One method is carried out in two steps.
  • the hair is first impregnated within an aqueous solution of one of said methyl derivatives of dihydroxy-io-indole, the pH of this solution being less than or equal to 7.
  • the color is then developed in situ by a second step consisting of the application of an aqueous solution containing an oxidizing reagent.
  • the following may be used as oxidizing reagents: hydrogen peroxide, sodium bromate, sodium percarbonate, sodium persulfate, ammonium persulfate, etc.
  • the oxidizing agent is added at the time of use to an aqueous solution of a nitrogen containing base, such as ammonia or an organic amine.
  • a nitrogen containing base such as ammonia or an organic amine.
  • suitable organic amines are mono-, di-, and triethanolamine and the methyl, dimethyl and diethylamines.
  • base is preferably between 1% and 4% by weight of the total solution.
  • ammonia or the organic bases may be used in the form of their salts, for example, as phosphates, carbonates, and bicarbonates.
  • ammonium persulfate or sodium persulfate may be used.
  • the persulfate selected may be added at the time of use to an aqueous solution of an organic acid, such. as lactic acid or monochloroacetic acid.
  • concentration of the organic acid should preferably be between 1% and 10% by weight.
  • the quantities of oxidizing agents used range preferably between 0. 1% and 6% by weight of the total solution.
  • the second step may simply consist of oxidation by exposure to the air.
  • a solution containing one of the said methyl derivatives of dihydroxy-5-6-indole is applied to the hair.
  • This solution is at a pH equal to or greater than 7.
  • concentration of the nitrogen containing solution which is prepared, immediately before the application to the hair, results from the mixture of two solutions A and B, solution A containing a methylated derivative of dihydrox*-5,6-indole and solution B being an oxidizing solution.
  • Solution A is an aqueous solution containing as hereinbefore indicated, one of the methylated derivatives of dihydroxy-5,6-indole, the pH of this solution being adjusted to be equal to or greater than 7.
  • the pH is adjusted by adding an alkaline agent, while taking care to exclude the air, by operating in a nitrogen atmosphere.
  • this alkaline agent may also be carried out in the presence of air, if there is added an organic or mineral reducing agent which retards the oxidizing action of the oxygen in the air.
  • the alkaline agents which may be used to regulate the pH are: ammonia, its salts, such as triammonium phosphate, ammonium carbonate, ammonium bicarbonate, and a mixture of ammonium hydroxide and caustic soda, etc., organic amines such as monoethanolamine, diethanolamine, triethanolamine, methylamine, ethylamine, dimethylamine, diethylamine, etc.
  • the concentration of the alkaline agents which is preferably between 1% and 1 5% by weight of the solution, is such that the pH is between 7 and 10.
  • the quantity of soda should not exceed 5% of the quantity of ammonia, that is to say, it should constitute no more than 0.75% by weight of the total solution.
  • the reducing agents which may be used to prevent the premature oxidation of the methyl derivative of dihydroxy-5,6-indole may be carboxylic mercaptans, such as thioglycolic acid, thiolactic acid, or mercapto alcohols, such as thioglycerol or even inorganic reducing agents, such as sodium sullite. Their concentration may vary between 0.1% and 1% of the total solution.
  • N-CHT-COZH O a-C ME
  • a certain quantity of sodium chloride may advantageously be added to the aqueous solution of the methyl ated derivatives of hydroxy-5,6-ind-ole. The addition of this salt produces certain shades of greater intensities for a given concentration of the indole derivatives.
  • the B solution is an aqueous solution containing an oxidizing agent and may be selected from the group comprising hydrogen peroxide, sodium bromate, sodium percarbonate, sodium persulfate, etc.
  • concentration of these oxidizing agents may vary from 0.2% to 12% of the oxidizing solution.
  • the solution is mixed at the time of use, volume for volume; the solution A of a methylated derivative of dihydroxy-5,6-indole and oxidizing agent B.
  • the mixture is applied directly to the hair and left in contact with it for a variable time, not greater than an hour, the hair is rinsed, lightly shampooed to eliminate any excess dye, and dried.
  • the process'according to the invention may be carried out, not only by means of aqueous solutions, but also by means of creams.
  • the methylated derivatives of dihydroxy-5,6-indole are incorporated into a base consisting of a cream, which may have either an acid or alkaline pH.
  • the hair may then be dyed in either one step or two.
  • the hair is first impregnated with the cream at an acid pH.
  • the cream is then removed by rinsing, and an oxidizingsolution, similar to the solution B, hereinbefore described, applied to the hair.
  • the cream containing the methylated derivative of dihydroxy-5,6-indole is mixed immediately before application with an oxidizing solution of the type B, 'hereinbefore described, and the mixture is then applied to the hair.
  • EXAMPLE 1 5,6-diacetoxyindole gr 1 Cemulsol 132 (a non-ionogen condensation product of ethylene oxide and a naphthol compound) gr 9 Monoethanolamine gr 2 Thioglycollic acid (50%) gr 0.1 Water to make cc 100
  • This solution of 5,6-diacetoxyindole was prepared in water with heating at about 5060 C. until complete dissolution of the various ingredients. This temperature increase brings about the deacetylation and therefore the formation of the 5, 6-hydroxyindole.
  • the solution thus prepared comprises no accelerating agent and may be applied several times in succession, thus causing a progressive darkening of the shade obtained.
  • EXAMPLE 2 5,6-diacetoxyindole gr 1 Cemulsol 132 gr 9 Ammonia (20%) gr 3 Thioglycollic acid (50%) gr 0.1 Water to make cc 100 To 50 cc. of this solution there are added, immediately before use, 5 cc. of a 6 percent hydrogen peroxide solution, the mixture then being applied to the hair and al- To 50 cc. of this solution there is added, immediately before use, 1 gr. of ammonium persulfate as an oxidizing agent. The solution is applied to the hair and allowed to act for 20 minutes. An ash blond coloring is obtained.
  • EXAMPLE 4 5,6-diacetoxyindole gr 1 Cemulsol 132 gr 9 Ammonia (20%) gr 3 Thioglycollic acid (50%) gr 0.1 Water to make cc To 50 cc. of this solution there is added, immediately before use, 0.1 gr. of cobalt chloride as an oxidation catalyst. The solution is applied to the hair and allowed to act for 20 minutes. A bluish-grey shade is obtained.
  • EXAMPLE 6 5,6-diacetoxyindole gr 1 Acetone gr 20 Diethanolamine gr 2 Thioglycollic acid (50%) gr 0.1 Water to make cc 100 This solution is applied to the hair and allowed to act for 20 minutes. The hair is then rinsed and 50 cc. of a 1% cobalt chloride solution (serving as oxidation catalyst) is applied, and allowed to act for 5 minutes. The hair is rinsed and a very distinctive dark ash blond color is obtained.
  • EXAMPLE 7 5,6-diacetoxyindole gr 1 Cemulsol 132 gr 9 Ammonia (20%) gr 3 Thioglycollic acid (50%) gr 0.1 Water to make cc 100 50 cc. of this solution are applied to the hair and allowed to act for 15 minutes. At the end of this period the hair is rinsed and 50 cc. of an ammoniacal silver nitrate solution equivalent to a 0.1 percent silver oxide content is appligd. A fine normal to dark chestnut shade is obtaine EXAMPLE 8 5,6-diacetoxyindole gr 1 Cemulsol 132 gr 9 Monoethanolamine gr 2 Thioglycollic acid (50%) gr 0.1 Water to make cc 100 50 cc.
  • EXAMPLE 10 5,6-diacetoxyindole gr 1 Cemulsol 132 gr 9 Ammonium carbonate gr 4 Thioglycollic acid (50%) gr 0.1 Water to make cc 100 50 cc. of this solution are applied to the hair and A cream product is prepared by emulsifying 20.parts of glycol stearate in 80 parts of a solution containing the 5,6 diacetoxyindole, monoethanolarnine, thioglycollic acid and Ce-mulsol 132, as described in Example 8. This cream is brushed on the hair and allowed to act for about 20 minutes. The hair is then rinsed and 50 cc. of an ammoniacal silver nitrate solution equivalent to a 0.1 percent silver oxide content are applied. A rather distinguished golden chestnut shade is obtained.
  • Methyl-Z-dihydroxy-S,6-indole gr 1 Ammonia (20%) gr 8 Thioglycollic acid gr 0.3 Ethylenediamine N-dihydroxyethyl-N'-diacetic acid (as sequestering agent) grN 0.2 Water to make cc 100 The pH of this solution is about 9.5.
  • both solutions may be mixed together and the resulting solution may be applied immediately to the hair.
  • the hair is dyed a less intense shade.
  • EXAMPLE 15 A solution is preparedcontaining: Dimethyl-2,3-dihydroxy-5,6-indole gr 4 Solution of methylamine (33%) gr l2 Complexing or sequestering agent of the recited type. gr 0.2 Water to make 100 Before the use this solution is mixed with a 1:1 volume ratio With an oxidizing solution containing:
  • a second solution is prepared containing:
  • Methyl-Z-dihydroxy-S,6-indole gr 1 Acetic acid cc 5 Water to make cc 100 This solution is applied to live grey hair, allowed to remain in contact therewith for 20 minutes, then there is applied a second solution having the same composition as the oxidizing solution called for in Example 19 and is applied in the same manner. A chestnut red shade is obtained.
  • a soltuion is prepared comprising:
  • Acetic acid cc 3 Water to make cr- 100 This solution is applied to grey hair, allowed to remain in contact therewith for 20 minutes, then there is applied the following solution:
  • EXAMPLE 27 The following solution is prepared: Methyl-Z-dihydroxy-S,6-indole gr 1.3 Butylglycol cc Acetic acid cc 2 Water to make cc 100 This solution is applied to grey hair and allowed to remain in contact therewith for 30 minutes with partial drying, then there is applied a second solution having the following composition:
  • EXAMPLE 28 The following solution is prepared: Dimethyl-'2,3-dihydroXy-5,6-indole gr 1.4 Butylglycol cc '12 Lactic acid cc 3 Water to make cc 100 This solution is applied to grey hair and allowed to remain in contact therewith for minutes. The hair is then rinsed and a second solution is applied, comprising: Monoethanolamine -gr 3 Ammonium persulfate gr 0.5 Urea gr 7.5 Water to make cc 100 This solution is allowed to remain in contact with the hair for 20 minutes, then rinsed, shampooed, rinsed the second time and dried. A golden blond color is obtained.
  • EXAMPLE 29 The following solution is prepared: Dimethyl'2,3-dihydroXy-5,6-indole gr 1 Butylglycol cc 10 Lactic acid cc 7 Water to make cc 100 T his solution is applied to live white hair, is allowed to remain in contact therewith for 30 minutes. The hair is allowed to partially dry and then there is applied thereto to the following solution:
  • EXAMPLE 32 The following solution is prepared: 7 Methyl-l-dihydroXy-5,6-ind0le gr 1.2 Butylglycol cc 10 Lactic acid cc 0.5 Water to make cc 100 This solution is applied to White hair and allowed to remain in contact therewith for 30 minutes. It is then rinsed and a second solution applied thereto, comprising:
  • EXAMPLE 34 Solution A comprises:
  • EXAMPLE 36 Solution A comprises:
  • Solutions A and B are mixed in equal volumes and then applied to white hair and allowed to remain in contact therewith for 30 minutes. The hair is then rinsed, shampooed, rinsed the second time and dried. A strong bluegrey color is obtained.
  • EXAMPLE 38 Solution A comprises:
  • Mcthyl-2-dihydroxy-5,6-indole gr 6 Butylglycol gr 30 Thioglycollic acid gr 1 Monoethanolamine gr 16 Sodium chloride gr 4 Sequestering agent gr 0.3 Water to make cc Solution B comprises:
  • Solution A comprises:
  • EXAMPLE 40 Solution A comprises:
  • Solution A comprises: Dimethyl-1,3-dihydroxy-5,6-indole gr 6 Butylglycol gr 30 Thioglycollic acid gr I Ammonium hydroxide (20%) gr 24 Sodium chloride gr 6 sequestering agent gr 0.4
  • EXAMPLE 42 Solution A comprises:
  • EXAMPLE 44 An acid cream is prepared as in the preceding example which comprises:
  • a process for dyeinghuman hair which comprises applying thereto an aqueous alkaline composition containing a compound represented by the formula in which R, R and R are selected from the group consisting of H and CH at least one of these radicals being CH and a nitrogeneous substance selected from the group consisting of ammonia, ammonium salts and amines; and applying thereto in a second step an aqueous solution of a water soluble synthetic inorganic oxidizing agent; and allowing said composition to remain in contact with said hair. until the desired shade is obtained.
  • a process for dyeing human hair which comprises saturating the fibrous material with an aqueous alkaline composition containing dihydroxy- 5,6-indole and a nitrogeneous substance selected from. the group consisting of ammonia, ammonium salts and amines; and a sufiicient amount of a water soluble syntheticinorganic oxidizing agent; and allowing said composition to remain in contact with said. hair until a desired shade is obtained.
  • a process for dyeing human hair which comprises applying thereto in a first step an aqueous alkaline composition containing a compound represented by the formula in which R, R and R are selected from the group consisting of H and CH at least one of these radicals being CH and a nitrogeneous substance selected from the group consisting of ammonia, ammonium salts and amines; rinsing said hair and applying thereto in a second step an ammoniacal silver nitrate solution.
  • a process for dyeing human hair which comprises saturating in a first step the fibrous material with an aqueous alkaline composition containing dihydroxy-5,6-indole and a nitrogeneous substance selected from the group consisting of ammonia, ammonium salts and amines; rinsing said fibrous material; and applying thereto in a second step an alkaline solution of a synthetic inorganic oxidizing agent.
  • a process according to claim 1 for dyeing human hair in which the oxidizing agent is applied to the hair after the hair has been impregnated with the oxidative dye substance.
  • a product suitable for dyeing live human hair by an oxidative process which comprises a water soluble solution of dihydroXy-5,6-indole having the formula in which R, R and R are selected from the group consisting of H and CH at least one of these radicals being 1% CH and the pH value of said solution being at least 7; and a nitrogeneous substance selected from the group consisting of ammonia, ammonium salts and amines; and a sufiicient amount of a water soluble oxidizing agent.
  • a product as claimed in claim 14 suitable for dyeing live human hair, in which the oxidative dye substance is methyl-1 dihydroxy-5,6-indole.
  • a product as claimed in claim 14 suitable for dyeing live human hair in which the oxidative dye substance is methyl-3 dihydroXy-5,6-indole.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
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US126749A 1959-07-24 1961-06-01 Processes and compositions for dyeing hair and similar fibres Expired - Lifetime US3194734A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US82921359A 1959-07-24 1959-07-24
FR829122A FR1264707A (fr) 1959-07-24 1960-06-03 Composition pour teindre les cheveux, procédé utilisé et produits obtenus

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US (1) US3194734A (ko)
BE (2) BE549801A (ko)
CH (1) CH395435A (ko)
DE (1) DE1193643B (ko)
ES (1) ES260079A1 (ko)
FR (2) FR1133594A (ko)
GB (2) GB797174A (ko)
NL (2) NL94284C (ko)

Cited By (36)

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US3898032A (en) * 1971-06-11 1975-08-05 Zotos Int Inc Oxidative hair-coloring mixtures containing a conditioning agent
US3899288A (en) * 1971-12-02 1975-08-12 Jean Galerne Keratinic fibres oxidation dyeing compositions containing a carbonate of an alkali metal amino acid
US3989447A (en) * 1970-10-19 1976-11-02 Societe Anonyme Dite: L'oreal Process for nonpermanently dyeing human hair with indamine indoaniline and indophenol hair dyes
US3993436A (en) * 1973-12-01 1976-11-23 Shiseido Co., Ltd. Dyeing live hair with melanin precursors
US4010872A (en) * 1968-08-28 1977-03-08 Dart Industries Inc. Oxidation hair dye in a plural-fluids dispensing package
US4013404A (en) * 1970-12-06 1977-03-22 American Cyanamid Company Method of dyeing hair with indolines, indoles and indazoles
US4208183A (en) * 1977-05-10 1980-06-17 L'oreal Process for improving the storage stability of indole dyestuffs
US4595765A (en) * 1983-09-19 1986-06-17 Clairol Incorporated Process for preparing 5,6-dihydroxyindole
DE3720143A1 (de) * 1986-06-16 1987-12-17 Oreal Faerbemittel fuer menschliche keratinfasern in form eines schaumes auf der grundlage von 5,6-dihydroxyindol
US4822375A (en) * 1986-03-06 1989-04-18 L'oreal Dyeing compositions for keratinous fibres based on indole derivatives, and new compounds
US4932977A (en) * 1988-11-21 1990-06-12 Clairol Incorporated Indole-aldehyde hair dyes
US4956174A (en) * 1986-03-06 1990-09-11 L'oreal Compositions for coloring the skin based on indole derivatives
US4961754A (en) * 1987-07-17 1990-10-09 L'oreal Ultrafine inorganic powder containing melanin pigments, process for preparation thereof and its use in cosmetics
US5167669A (en) * 1989-07-21 1992-12-01 L'oreal Composition for dyeing keratinous fibers employing an indole dye and at least one para-phenylenediamine containing a secondary amino group and process for use
US5173085A (en) * 1982-12-07 1992-12-22 Clairol Incorporated Hair dyeing process and compositons package
US5273550A (en) * 1991-09-26 1993-12-28 Clairol Incorporated Process and kit for dyeing hair
US5279618A (en) * 1991-09-26 1994-01-18 Clairol Incorporated Process and kit for dyeing hair
US5346509A (en) * 1988-05-12 1994-09-13 Clairol Incorporated Process for dyeing hair by the sequential treatment of hair with metal ion-containing composition and with a dye composition containing 5,6-dihydroxyindole-2-carboxylic acid and certain derivatives thereof
US5413612A (en) * 1992-04-29 1995-05-09 Clairol Incorporated Composition and method for dyeing hair with indolic compounds in the presence of a chlorite oxidant
US5516916A (en) * 1985-08-02 1996-05-14 Clairol Incorporated Process for preparing dye compositions containing 5,6-dihydroxyindole
US5686084A (en) * 1995-12-06 1997-11-11 Clairol Incorporated Synthesis of quaternary melanin compounds and their use as hair dyes or for skin treatment
US5702712A (en) * 1995-12-06 1997-12-30 Clairol, Incorporated Melanoquaternary compounds and their use as hair dyes and for skin treatment
US5792220A (en) * 1997-05-16 1998-08-11 Bristol-Myers Squibb Company Dyeing hair with melanin procursors in the presence of iodate and peroxide
US6160127A (en) * 1998-07-15 2000-12-12 Bristol-Myers Squibb Company Process for the preparation of substituted indoles
US6258131B1 (en) 1988-04-12 2001-07-10 L'oreal Process for preserving the dyeing capacity of 5, 6-dihydroxyindole and of its and derivatives in an aqueous medium, composition and dyeing process
US6537330B1 (en) 1998-06-23 2003-03-25 Henkel Kommanditgesellschaft Auf Aktien Colorants
US6569211B2 (en) 1991-11-19 2003-05-27 Henkel Kommanditgesellschaft Auf Aktien 5,6-dihydroxyindolines as additives for hair dyeing preparations
EP1352630A2 (fr) * 2002-04-08 2003-10-15 L'oreal Procédé de gainage métallique conférant aux fibres kératiniques des propriétés cosmétiques rémanentes aux shampoings
US20030223944A1 (en) * 2002-04-08 2003-12-04 Aude Livoreil Metallic coating process for giving keratin fibres shampoo-remanent cosmetic properties
US6719811B1 (en) * 1990-05-19 2004-04-13 Henkel Kommanditgesellschaft Auf Aktien Oxidation colorants for keratin fibers
US6743264B2 (en) 2002-02-14 2004-06-01 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Two step permanent coloring of hair
US20050000035A1 (en) * 2003-07-03 2005-01-06 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Method of providing more vibrant, natural and long-lasting color to hair
US20050000036A1 (en) * 2003-07-03 2005-01-06 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Hair dyeing method including an aligning step
EP1704847A1 (en) * 2005-03-23 2006-09-27 Wella Aktiengesellschaft Cosmetic agents and methods of mirrorizing keratin fibres
EP1649899B1 (de) * 2004-10-22 2008-08-13 TANA-Cosmetics MANOA Kurt Fortmann GmbH & CO. KG Mittel und Zubereitung zum Färben von Haaren
WO2013078492A2 (de) 2011-11-28 2013-06-06 Gw Cosmetics Gmbh Mittel und verfahren zur färbung von keratinfasern

Families Citing this family (14)

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NL224577A (ko) * 1957-02-02
BE593306A (ko) * 1959-07-24
DE1265699B (de) * 1959-11-07 1968-04-11 Basf Ag Faerben und Bedrucken von Wolle, Haaren, Leder und Pelzen mit sulfonsaeuregruppenfreien Farbstoffen
CA1201067A (en) * 1982-12-07 1986-02-25 Keith Brown Hair dyeing process and composition
LU86256A1 (fr) * 1986-01-20 1988-01-20 Oreal Procede de teinture des fibres keratiniques avec du 5,6-dihydroxyindole associe avec un iodure
CH676845A5 (ko) * 1986-11-07 1991-03-15 Oreal
LU86668A1 (fr) * 1986-11-17 1988-06-13 Oreal Procede de teinture des fibres keratiniques avec des derives d'indole associes avec un iodure
LU86833A1 (fr) * 1987-04-02 1988-12-13 Oreal Procede de teinture des fibres keratiniques avec le 5,6-dihydroxyindole associe a un iodure et une composition de peroxyde d'hydrogene a ph alcalin
FR2649886B1 (fr) * 1989-07-21 1991-10-11 Oreal Composition de teinture des fibres keratiniques mettant en oeuvre un colorant indolique et au moins une paraphenylenediamine comportant un groupement amino secondaire et procede de mise en oeuvre
FR2722685B1 (fr) * 1994-07-22 1997-03-21 Oreal Utilisation d'un sel de manganese, de zinc et de cobalt dans un procede de teinture en un temps mettant en oeuvre un compose indolique
FR2722684A1 (fr) * 1994-07-22 1996-01-26 Oreal Utilisation d'un sel metallique dans un procede de teinture en deux temps mettant en oeuvre un compose indolique
FR2722686B1 (fr) 1994-07-22 1996-08-30 Oreal Set, procede, dispositif et composition de teinture des fibres keratiniques
JP2003512686A (ja) 1999-10-21 2003-04-02 キュービック コーポレイション 運賃カードに値を迅速に分配し付加するためのシステム
CN110123670A (zh) * 2019-06-12 2019-08-16 四川大学 一种树枝状大分子催化染发剂及其制备和使用方法

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US4010872A (en) * 1968-08-28 1977-03-08 Dart Industries Inc. Oxidation hair dye in a plural-fluids dispensing package
US3989447A (en) * 1970-10-19 1976-11-02 Societe Anonyme Dite: L'oreal Process for nonpermanently dyeing human hair with indamine indoaniline and indophenol hair dyes
US4013404A (en) * 1970-12-06 1977-03-22 American Cyanamid Company Method of dyeing hair with indolines, indoles and indazoles
US3898032A (en) * 1971-06-11 1975-08-05 Zotos Int Inc Oxidative hair-coloring mixtures containing a conditioning agent
US3899288A (en) * 1971-12-02 1975-08-12 Jean Galerne Keratinic fibres oxidation dyeing compositions containing a carbonate of an alkali metal amino acid
US3993436A (en) * 1973-12-01 1976-11-23 Shiseido Co., Ltd. Dyeing live hair with melanin precursors
US4208183A (en) * 1977-05-10 1980-06-17 L'oreal Process for improving the storage stability of indole dyestuffs
US5173085A (en) * 1982-12-07 1992-12-22 Clairol Incorporated Hair dyeing process and compositons package
US4595765A (en) * 1983-09-19 1986-06-17 Clairol Incorporated Process for preparing 5,6-dihydroxyindole
US5516916A (en) * 1985-08-02 1996-05-14 Clairol Incorporated Process for preparing dye compositions containing 5,6-dihydroxyindole
US4822375A (en) * 1986-03-06 1989-04-18 L'oreal Dyeing compositions for keratinous fibres based on indole derivatives, and new compounds
US4956174A (en) * 1986-03-06 1990-09-11 L'oreal Compositions for coloring the skin based on indole derivatives
US4900326A (en) * 1986-06-16 1990-02-13 L'oreal Dye composition for human keratinous fibres in the form of foam, based on 5,6-dihydroxyindole
DE3720143A1 (de) * 1986-06-16 1987-12-17 Oreal Faerbemittel fuer menschliche keratinfasern in form eines schaumes auf der grundlage von 5,6-dihydroxyindol
DE3720143C2 (de) * 1986-06-16 1998-09-24 Oreal Färbemittel für menschliche Keratinfasern in Form eines Schaumes auf der Grundlage von 5,6-Dihydroxyindol
US4961754A (en) * 1987-07-17 1990-10-09 L'oreal Ultrafine inorganic powder containing melanin pigments, process for preparation thereof and its use in cosmetics
AT400806B (de) * 1987-07-17 1996-03-25 Oreal Puder, verfahren zur herstellung eines kosmetischen puders, sowie kosmetisches mittel zur färbung der haare oder zum schminken der haut
US6258131B1 (en) 1988-04-12 2001-07-10 L'oreal Process for preserving the dyeing capacity of 5, 6-dihydroxyindole and of its and derivatives in an aqueous medium, composition and dyeing process
US5346509A (en) * 1988-05-12 1994-09-13 Clairol Incorporated Process for dyeing hair by the sequential treatment of hair with metal ion-containing composition and with a dye composition containing 5,6-dihydroxyindole-2-carboxylic acid and certain derivatives thereof
US4932977A (en) * 1988-11-21 1990-06-12 Clairol Incorporated Indole-aldehyde hair dyes
US5167669A (en) * 1989-07-21 1992-12-01 L'oreal Composition for dyeing keratinous fibers employing an indole dye and at least one para-phenylenediamine containing a secondary amino group and process for use
US6719811B1 (en) * 1990-05-19 2004-04-13 Henkel Kommanditgesellschaft Auf Aktien Oxidation colorants for keratin fibers
US5279617A (en) * 1991-09-26 1994-01-18 Clairol Incorporated Process and kit for dyeing hair
US5279618A (en) * 1991-09-26 1994-01-18 Clairol Incorporated Process and kit for dyeing hair
US5273550A (en) * 1991-09-26 1993-12-28 Clairol Incorporated Process and kit for dyeing hair
US6569211B2 (en) 1991-11-19 2003-05-27 Henkel Kommanditgesellschaft Auf Aktien 5,6-dihydroxyindolines as additives for hair dyeing preparations
US5413612A (en) * 1992-04-29 1995-05-09 Clairol Incorporated Composition and method for dyeing hair with indolic compounds in the presence of a chlorite oxidant
US5686084A (en) * 1995-12-06 1997-11-11 Clairol Incorporated Synthesis of quaternary melanin compounds and their use as hair dyes or for skin treatment
US5702712A (en) * 1995-12-06 1997-12-30 Clairol, Incorporated Melanoquaternary compounds and their use as hair dyes and for skin treatment
US6313313B1 (en) * 1995-12-06 2001-11-06 Bristol-Myers Squibb Company Synthesis of melanoquaternary compounds and their use as hair dyes and for skin treatment
US5792220A (en) * 1997-05-16 1998-08-11 Bristol-Myers Squibb Company Dyeing hair with melanin procursors in the presence of iodate and peroxide
WO1998051269A1 (en) * 1997-05-16 1998-11-19 Bristol-Myers Squibb Company Dyeing hair with melanin precursors in the presence of iodate and peroxide
US6537330B1 (en) 1998-06-23 2003-03-25 Henkel Kommanditgesellschaft Auf Aktien Colorants
US6160127A (en) * 1998-07-15 2000-12-12 Bristol-Myers Squibb Company Process for the preparation of substituted indoles
US6743264B2 (en) 2002-02-14 2004-06-01 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Two step permanent coloring of hair
US20030223944A1 (en) * 2002-04-08 2003-12-04 Aude Livoreil Metallic coating process for giving keratin fibres shampoo-remanent cosmetic properties
EP1352630A3 (fr) * 2002-04-08 2004-03-24 L'oreal Procédé de gainage métallique conférant aux fibres kératiniques des propriétés cosmétiques rémanentes aux shampoings
EP1352630A2 (fr) * 2002-04-08 2003-10-15 L'oreal Procédé de gainage métallique conférant aux fibres kératiniques des propriétés cosmétiques rémanentes aux shampoings
US20050000035A1 (en) * 2003-07-03 2005-01-06 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Method of providing more vibrant, natural and long-lasting color to hair
US20050000036A1 (en) * 2003-07-03 2005-01-06 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Hair dyeing method including an aligning step
US7060111B2 (en) 2003-07-03 2006-06-13 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Method for providing more vibrant, natural and long-lasting color to hair
US7074244B2 (en) 2003-07-03 2006-07-11 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Hair dyeing method including an aligning step
EP1649899B1 (de) * 2004-10-22 2008-08-13 TANA-Cosmetics MANOA Kurt Fortmann GmbH & CO. KG Mittel und Zubereitung zum Färben von Haaren
EP1704847A1 (en) * 2005-03-23 2006-09-27 Wella Aktiengesellschaft Cosmetic agents and methods of mirrorizing keratin fibres
WO2006102024A1 (en) * 2005-03-23 2006-09-28 The Procter & Gamble Company Cosmetic agents and methods of mirrorizing keratin fibres
US20060249170A1 (en) * 2005-03-23 2006-11-09 Thomas Kripp Cosmetic agents and methods of mirrorizing keratin fibres
WO2013078492A2 (de) 2011-11-28 2013-06-06 Gw Cosmetics Gmbh Mittel und verfahren zur färbung von keratinfasern
US9125842B2 (en) 2011-11-28 2015-09-08 Gw Cosmetics Gmbh Agent and method for coloring keratin fibers

Also Published As

Publication number Publication date
GB797174A (en) 1958-06-25
NL94284C (ko)
DE1193643B (de) 1965-05-26
CH395435A (fr) 1965-07-15
BE549801A (ko)
BE593306A (ko)
GB887579A (en) 1962-01-17
FR1133594A (fr) 1957-03-28
ES260079A1 (es) 1960-12-16
FR1264707A (fr) 1961-06-23
NL254075A (ko)

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