EP2010482A1 - Copulants et compositions de coloration capillaire les contenant - Google Patents

Copulants et compositions de coloration capillaire les contenant

Info

Publication number
EP2010482A1
EP2010482A1 EP07727938A EP07727938A EP2010482A1 EP 2010482 A1 EP2010482 A1 EP 2010482A1 EP 07727938 A EP07727938 A EP 07727938A EP 07727938 A EP07727938 A EP 07727938A EP 2010482 A1 EP2010482 A1 EP 2010482A1
Authority
EP
European Patent Office
Prior art keywords
hydrogen
hydroxy
amino
crc
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP07727938A
Other languages
German (de)
English (en)
Inventor
Jürgen KÜHLWEIN
Werner Russ
Dominic Pratt
Hartmut Möhring
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dystar Colours Distribution GmbH
Kao Corp SA
Original Assignee
Dystar Textilfarben GmbH and Co Deutschland KG
Kao Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dystar Textilfarben GmbH and Co Deutschland KG, Kao Corp filed Critical Dystar Textilfarben GmbH and Co Deutschland KG
Priority to EP07727938A priority Critical patent/EP2010482A1/fr
Publication of EP2010482A1 publication Critical patent/EP2010482A1/fr
Withdrawn legal-status Critical Current

Links

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
    • 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
    • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • A61K8/55—Phosphorus compounds
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C307/04—Diamides of sulfuric acids
    • C07C307/10—Diamides of sulfuric acids having nitrogen atoms of the sulfamide groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/11—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/31—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms
    • C07C311/32—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/247—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aromatic amines (N-C aromatic linkage)

Definitions

  • the present invention relates to novel coupling compounds and hair dye compositions containing them.
  • Oxidation bases are colourless or weakly coloured compounds, such as ortho- or para-phenylenediamines, ortho- or para-aminophenols or heterocyclic compounds and react with oxidizing agents to give coloured compounds.
  • the obtained shades can be varied by combining the oxidation bases with couplers, such as aromatic meta-diamines, meta-aminophenols, meta-hydroxyphenols and certain heterocyclic compounds.
  • couplers such as aromatic meta-diamines, meta-aminophenols, meta-hydroxyphenols and certain heterocyclic compounds.
  • a variety of oxidation bases and couplers can be used to enable to get a broad range of different shades.
  • the permanent colours obtained by using these oxidation dyes need to fulfil some requirements. They should be safe, provide good intensity evenly along the hair shaft, should be stable to external influences, such as shampooing, light, sweat and rubbing and should enable the coverage of grey hair.
  • the dyes should also be stable in the formulation.
  • m-Phenylendiamines and their use as coupling compounds to produce oxidation dyes for hair dyeing are known and for example described in DE 35 21 995 A1 , WO1988/00042, WO1993/010744, DE 102 60 834 A1 and WO2004/058204.
  • the present invention refers to compounds of the formula (I) wherein
  • R 1 is (CrC 4 )-alkyl, (CrC 4 )-alkyl which is substituted by hydroxy, (CrC 4 )-alkoxy, hydroxy-(CrC 4 )-alkoxy, CN, -COOR 5 , -CON(R 5 ) 2 or -N(R 5 ) 2 or is phenyl;
  • R 2 is hydrogen, methyl or ethyl;
  • R 4 is hydrogen, (C 2 -C 4 )-alkyl which is substituted by hydroxy, (CrC 4 )-alkoxy or hydroxy-(CrC 4 )-alkoxy; each of R 5 , independently is hydrogen, (CrC 4 )-alkyl or hydroxy-(C 2 -C 4 )-alkyl;
  • R 3 is not -SO 2 CH 3 if R 2 and R 4 are both hydrogen and R 1 is methyl, -CH 2 COOC 2 H 5 Or -C 2 H 5 NHiC 3 H 7 ; whereas R 3 is not -SO 2 CF 3 if R 2 and R 4 are both hydrogen and R 1 is methyl; and whereas R 1 is not phenyl if R 3 is -SO 2 CH 3 , -SO 2 C 2 H 5 , -SO 2 nC 4 H 9 , -SO 2 CF 3 or -SO 2 CHF 2 and R 2 and R 4 are both hydrogen.
  • (CrC 4 )-Alkyl groups may be straight-chain or branched and are for example methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, isopentyl or n-hexyl.
  • alkoxy groups which accordingly are for example methoxy and ethoxy.
  • Halogen is preferably fluorine, chlorine, bromine and iodine.
  • the compounds of the formula (I) can be present in form of their acid addition salts of organic or inorganic acids.
  • acid additions salts are cosmetically acceptable salts like chlorides, sulfates, phosphates, acetates, propionates, lactates and citrates.
  • R 2 is preferably hydrogen and R 1 is preferably not ethyl in case R 3 is -
  • N NHHSSOO 22 ( CH 3 and R 2 and R 4 are both hydrogen. Also, R 1 is preferably other than phenyl.
  • R 1 is methyl, ethyl, hydroxyethyl, methoxyethyl or -CH 2 COOR 5 ;
  • R 2 is hydrogen;
  • R 4 is hydrogen or methyl or ethyl, which is substituted by hydroxy; and each of R 5 , independently is hydrogen, methyl, ethyl or hydroxyethyl, whereas R 3 is not -NHSO 2 CH 3 if R 4 is hydrogen and R 1 is methyl.
  • Examples of especially preferred compounds of formula (I) are the compounds of formulae (Ia) to (Ih)
  • inventive compounds of formula (I) can be prepared by methods which are in principle known to a person of ordinary skill in the art and which are described in literature, for example in the patent literature cited above.
  • R 1 and R 2 are defined as given above and Y is a group which can be transferred into an amino group, can be reacted with a compound of the formula (III) R 3 -Hal (III) wherein R 3 is defined as given above and Hal is a halogen atom, preferably chlorine, to a compound of the formula (IV)
  • R 1 to R 3 are defined as given above.
  • a group Y which can be transferred into an amino group, with other words which is a protected amino group, is preferably the acetylamino group or the nitro group.
  • the acetylamino group can be deacetylized to form the amino group and the nitro group can be reduced to form the amino group, both being methods known to a skilled person.
  • the compound of formula (Ma) can be obtained by reacting a compound of formula (VII)
  • inventive compounds of the formula (I) can advantageously be used as couplers which by reacting with developers form oxidation dyes for hair dyeing, especially human hair dyeing.
  • the present invention also refers to hair dye compositions comprising at least one compound of the formula (I)
  • R 1 is (CrC 4 )-alkyl, (CrC 4 )-alkyl which is substituted by hydroxy, (CrC 4 )-alkoxy, hydroxy-(CrC 4 )-alkoxy, CN, -COOR 5 , -CON(R 5 ) 2 or -N(R 5 ) 2 or is phenyl;
  • R 2 is hydrogen, methyl or ethyl;
  • R 4 is hydrogen, (C 2 -C 4 )-alkyl which is substituted by hydroxy, (CrC 4 )-alkoxy or hydroxy-(CrC 4 )-alkoxy; each o Dff RR 55 ,, iinnddeeppeennddeennttllyy iiss hhyyddirogen, (CrC 4 )-alkyl or hydroxy-(C 2 -C 4 )-alkyl; whereas R 3 is not -SO 2 CH 3 if R 2
  • inventive hair dye compositions preferably comprise in addition to the compounds of the formula (I) as couplers one or more developers, which couplers and developers are capable to form an oxidation dye for hair dyeing.
  • Preferred developers are p-phenylenediamine derivatives such as benzene-1 ,4- diamine (commonly known as p-phenylenediamine), 2-methyl-benzene-1 ,4-diamine, 2-chloro-benzene-1 ,4-diamine, N-phenyl-benzene-1 ,4-diamine, N-(2- ethoxyethyl)benzene-1 ,4-diamine, 2-[(4-amino-phenyl)-(2-hydroxy-ethyl)-amino]- ethanol (commonly known as N,N-bis(2-hydroxyethyl)-p-phenylenediamine) (2,5- diamino-phenyl)-methanol, 1 -(2,5-diamino-phenyl)-ethanol, 2-(2,5-diamino-phenyl)- ethanol, N-(4-aminophenyl)benzene-1 ,4
  • the hair dye compositions according to the present invention can in addition to the compounds of the formula (I) comprise further couplers.
  • Such further couplers are preferred couplers as normally used to produce oxidation dyes for hair dyeing.
  • couplers examples include phenols, resorcinol and naphthol derivatives such as naphthalene-1 ,7-diol, benzene-1 ,3-diol, 4-chlorobenzene-1 ,3-diol, naphthalen-1-ol, 2-methyl-naphthalen-1-ol, naphthalene-1 ,5-diol, naphthalene-2,7-diol, benzene-1 ,4- diol, 2-methyl-benzene-1 ,3-diol, 7-amino-4-hydroxy-naphthalene-2-sulfonic acid, 2- isopropyl-5-methylphenol, 1 ,2,3,4-tetrahydro-naphthalene-1 ,5-diol, 2-chloro- benzene-1 ,3-diol, 4-hydroxy-naphthalene-1-sulfonic acid, benzene
  • the inventive hair dye compositions usually contain couplers at a total concentration of 0.001 to 10%, preferably 0.005 to 7.5% and more preferably 0.01 to 5% by weight, based on the weight of the hair dyeing composition and developers at a total concentration of 0.001 to 10%, preferably 0.005 to 7.5% and more preferably 0.01 to 5% by weight, calculated based on the weight of the hair dyeing composition.
  • the hair dye compositions according to the present invention can additionally comprise at least one direct dye.
  • direct dyes can be cationic, anionic or neutral and can be of natural or synthetic origin.
  • Preferred natural dyes are plant dyestuffs. Suitable dyes of such types are known on the market for hair colouring applications.
  • Suitable cationic dyestuffs are for example Basic Blue 6, Basic Blue 7, Basic Blue 9, Basic Blue 26, Basic Blue 41 , Basic Blue 99, Basic Brown 4, Basic Brown 16, Basic Brown 17, Natural Brown 7, Basic Green 1 , Basic Red 2, Basic Red 12 Basic Red 22, Basic Red 51 , Basic Red 76, Basic Violet 1 , Basic Violet 2, Basic Violet 3, Basic Violet 10, Basic Violet 14, Basic Yellow 57, Basic Orange 31 and Basic Yellow 87. Additional examples are the dyes disclosed in WO 95/15144 which are included herein by reference.
  • the hair dye compositions according to the present invention can contain cationic dyestuffs at a concentration of 0.001 to 2%, preferably 0.005 to 1.5% and more preferably 0.01 to 1% by weight, based on the weight of the hair dyeing composition.
  • Suitable anionic dyes are Acid Black 1 , Acid Blue 1 , Acid Blue 3, Food Blue 5, Acid Blue 7, Acid Blue 9, Acid Blue 74, Acid Orange 3, Acid Orange 6, Acid Orange 7, Acid Orange 10, Acid Red 1 , Acid Red 14, Acid Red 18, Acid Red 27, Acid Red 50, Acid Red 52, Acid Red 73, Acid Red 87, Acid Red 88, Acid Red 92, Acid Red 155, Acid Red 180, Acid Violet 9, Acid Violet 43, Acid Violet 49, Acid Yellow 1 , Acid Yellow 23, Acid Yellow 3, Food Yellow No. 8, D&C Brown No. 1 , D&C Green No. 5, D&C Green No. 8, D&C Orange No. 4, D&C Orange No. 10, D&C Orange No. 11 , D&C Red No. 21 , D&C Red No. 27, D&C Red No.
  • the hair dye compositions according to the present invention can contain anionic dyestuffs at a concentration of 0.001 to 2%, preferably 0.005 to 1.5% and more preferably 0.01 to 1% by weight, based on the weight of the hair dyeing composition.
  • Suitable neutral dyes are HC Blue No.2, HC Blue No.4, HC Blue No.5, HC Blue No.6, HC Blue No.7, HC Blue No.8, HC Blue No.9, HC Blue No.10, HC Blue No.11 , HC Blue No.12, HC Blue No.13, HC Brown No.1 , HC Brown No.2, HC Green No.1 , HC Orange No.1 , HC Orange No.2, HC Orange No.3, HC Orange No.5, HC Red BN, HC Red No.1 , HC Red No.3, HC Red No.7, HC Red No.8, HC Red No.9, HC Red No.10, HC Red No.11 , HC Red No.13, HC Red No.54, HC Red No.14, HC Violet BS, HC Violet No.1 , HC Violet No.2, HC Yellow No.2, HC Yellow No.4, HC Yellow No.5, HC Yellow No.10, HC Blue No.11
  • Suitable plant dyestuffs are henna (red or black), alkanna root, laccaic acid, indigo, logwood powder, madder root and rhubarb powder.
  • the pH of the hair dye compositions according to the present invention may range from 3 to 12, preferably from 5 to 11. The pH might be adjusted to the desirable value by the use of acidifying and alkalising agents.
  • Suitable acidifying agents are for example mineral and organic acids, such as hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, and lactic acid, and sulphonic acids.
  • Suitable alkalizing agents are for example aqueous ammonia, alkali metal carbonates, alkalonamine such as monoethanolamine, diethanolamine, and triethanolamine, and derivatives thereof, sodium hydroxide.
  • alkali metal carbonates such as monoethanolamine, diethanolamine, and triethanolamine, and derivatives thereof, sodium hydroxide.
  • Such an optional component examples include hydrocarbons such as squalane; animal or vegetable fats and oils; higher fatty acids such as oleic acid; organic solvents such as 1 ,2-propylene glycol; penetration promoters; cationic surfactants; natural or synthetic polymers; higher alcohols such as cetearyl alcohol; ethers; amphoteric surfactants; nonionic surfactants such as stearoyl monoethanolamide, coconut monoethanolamide, propylene glycol monostearate, polyoxyethylene (5) coconut amide, anionic surfactants such as sodium cetyl sulfate, sodium stearyl sulfate, potassium stearate, sodium stearate, polyoxyethylene (5) oleyl ether phosphate; protein derivatives; active ingredients such as coenzyme Q10; amino acids; antiseptics; chelating agents; stabilizers; antioxidants; plant extracts; crude drug extracts; vitamins such as retinyl palmitate; colorants; perfumes; catalysts such as potassium
  • the hair dye compositions of the present invention can be prepared in a conventional manner by mixing the components in the required amounts.
  • the hair dye compositions of the present invention In order to use the hair dye compositions of the present invention to dye hair they have to be mixed with an oxidation agent, which allows the formation of an oxidation dye by reaction of the coupler component with the developer component and which is usually called developer composition.
  • an oxidation agent which allows the formation of an oxidation dye by reaction of the coupler component with the developer component and which is usually called developer composition.
  • Preferred oxidation agents are peroxide containing agents, particularily hydrogen peroxide, or precursors thereof. Also suitable are urea peroxide, sodium perborate, sodium percarbonate, melamine peroxide, and persulfates such as ammonium persulfate, sodium persulfate and potassium persulfate. Oxygen can also be used as oxidation agent.
  • hydrogen peroxide or its addition compounds with urea, melamine, sodium borate or sodium carbonate are used in the form of a 1% to 20%, preferably 2% to 15 %, most preferably 2% to 12% preparation.
  • the hair dye composition according to the present invention as well as the oxidation agent can be present in the form of powder, transparent liquid, emulsion, cream, gel, paste, aerosol, aerosol foam or the like.
  • the present application also refers to a hair dyeing kit which comprises in separate containers a hair dye composition according to the present invention, a developer composition and optionally further components. Such further components are for example a shampoo, a conditioning composition, a hair treatment product, gloves and instructions for use.
  • the hair dye composition according to the present invention and the developer composition (oxidation agent) are mixed just before hair dyeing and the mixture is applied to the hair in a sufficient amount, which depends on the hair abundance, generally from about 60 to 200 grams.
  • the mixture is then allowed to act on the hair for about 10 to about 45 minutes, preferably about 30 minutes, at about 15 to 50 0 C. Thereafter, the hair is rinsed with water and dried. If necessary, it is washed with a shampoo. Subsequently the hair is dried.
  • the hair dye composition according to the present invention provides hair dyeing which has good uptake, good selectivity, as well as good stability to light and shampooing with improved brilliance.
  • Solvent was removed by evaporation, the residue was taken up with water and undissolved material was isolated by filtration.
  • Example 3 N-(5-Amino-2-methoxyphenyl)-dimethylsulfamoyl amide (compound of the formula (Ic) Use of 5,8 ml of dimethylsulfamoylchloride resulted in 7,8 g of acetylated intermediate (54,1 %). Deacetylation was performed in diluted sulphuric acid, 30 % within 1 hour at 100 0 C. After neutralization the product was isolated by filtration. Yield: 5,6 g (82,2%)
  • Example 6 N-(5-Amino-2-(2-methoxyethoxy)phenyl)-methanesulfonamide (compound of formula If)) a) 2-(2-Methoxyethoxy)-5-nitrophenylamine 48 ml of methylglycol was mixed with 81 g of 2,4-dinitrochlorobenzene. 17,2 g of solid sodium hydroxyde was added in portions in such a manner, that reaction temperature didn ' t exceed 35°C. Stirring was continued until all sodium hydroxide has dissolved. After dilution with 100 ml of water a solution of 88,6 g of NaHS x H2O was added dropwise between 70 and 80 0 C.
  • Example 9 (4-Amino-2-methanesulfonylamino-phenoxy)-acetic acid (compound of formula (Im)) a) (2-Acetylamino-4-nitro-phenoxy)-acetic acid ethylester
  • Example 11 N-(5-Amino-2-cyanomethoxy-phenyl)-methanesulfonamide (compound of formula (Ij))
  • the procedure of example 9 was repeated with the exception that 4,15 g of chloroacetonitrile were used instead of 6,75 g of chloroacetic acidethylester. Yield: 7,72 g (63,9% over all steps)
  • Dye Compositions were produced: iso-propanol 5.0 % ammonia 25% active 5.0 % sodium sulfite 1.0 % hydrogen peroxide 3.0 % developer (I to Vl; see below) 0.4 % coupler (inventive compound; see below) 0.4 % water up to 100 %
  • the Dye Compositions mentioned above were applied to undamaged white goat hair in amounts of approximately 1 g per g of hair at 50 0 C for 15min. or at 30 0 C for 30min. At the end of the processing time the tresses were rinsed with water, shampooed and then dried.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne des composés de formule (I), dans laquelle R1, R2, R3 et R4 sont tels que définis dans la revendication 1, ainsi que des compositions de coloration capillaire contenant lesdits composés.
EP07727938A 2006-04-18 2007-04-10 Copulants et compositions de coloration capillaire les contenant Withdrawn EP2010482A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP07727938A EP2010482A1 (fr) 2006-04-18 2007-04-10 Copulants et compositions de coloration capillaire les contenant

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP06009090A EP1847528A1 (fr) 2006-04-18 2006-04-18 Composés de couplage et compositions de teinture pour cheveux les contenant
PCT/EP2007/053470 WO2007118817A1 (fr) 2006-04-18 2007-04-10 Copulants et compositions de coloration capillaire les contenant
EP07727938A EP2010482A1 (fr) 2006-04-18 2007-04-10 Copulants et compositions de coloration capillaire les contenant

Publications (1)

Publication Number Publication Date
EP2010482A1 true EP2010482A1 (fr) 2009-01-07

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Family Applications (2)

Application Number Title Priority Date Filing Date
EP06009090A Withdrawn EP1847528A1 (fr) 2006-04-18 2006-04-18 Composés de couplage et compositions de teinture pour cheveux les contenant
EP07727938A Withdrawn EP2010482A1 (fr) 2006-04-18 2007-04-10 Copulants et compositions de coloration capillaire les contenant

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Application Number Title Priority Date Filing Date
EP06009090A Withdrawn EP1847528A1 (fr) 2006-04-18 2006-04-18 Composés de couplage et compositions de teinture pour cheveux les contenant

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EP (2) EP1847528A1 (fr)
TW (1) TW200740725A (fr)
WO (1) WO2007118817A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023163903A1 (fr) * 2022-02-25 2023-08-31 Henkel Ag & Co. Kgaa Agent de coloration oxydant pour fibres de kératine comprenant de nouvelles combinaisons de précurseurs de coloration

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NL174644C (nl) * 1970-04-13 1984-07-16 Minnesota Mining & Mfg Werkwijze ter bereiding van een herbicide verbinding; tevens werkwijze voor de bereiding van een preparaat met herbicide werking.
DE3521995A1 (de) * 1985-06-20 1987-01-02 Wella Ag 3-mesylamino-anilinverbindungen, verfahren zu ihrer herstellung sowie oxidationshaarfaerbemittel mit einem gehalt an diesen verbindungen
JPH05262718A (ja) * 1992-03-23 1993-10-12 Taisho Pharmaceut Co Ltd ５−置換アミノ−２−フェノキシスルホンアニリド化合物
WO1994019318A1 (fr) * 1993-02-19 1994-09-01 Taisho Pharmaceutical Co., Ltd. Compose de 5-aminoacetylaminosulfonanilide
US5854245A (en) * 1996-06-28 1998-12-29 Merck & Co., Inc. Fibrinogen receptor antagonists
US6300368B1 (en) * 1998-06-30 2001-10-09 Mitsui Chemicals, Inc. Anilide derivatives and antiarrhythmic agents containing the same
FR2816501B1 (fr) * 2000-11-14 2003-03-28 Oreal Utilisation de 2-sulphonylamino-phenols comme coupleurs en coloration d'oxydation

Non-Patent Citations (1)

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Title
See references of WO2007118817A1 *

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Publication number Publication date
TW200740725A (en) 2007-11-01
WO2007118817A1 (fr) 2007-10-25
EP1847528A1 (fr) 2007-10-24

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