NO300953B1 - Use of a direct-dye with at least one other direct-dye - Google Patents
Use of a direct-dye with at least one other direct-dye Download PDFInfo
- Publication number
- NO300953B1 NO300953B1 NO932907A NO932907A NO300953B1 NO 300953 B1 NO300953 B1 NO 300953B1 NO 932907 A NO932907 A NO 932907A NO 932907 A NO932907 A NO 932907A NO 300953 B1 NO300953 B1 NO 300953B1
- Authority
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- Norway
- Prior art keywords
- hair
- dye
- dyes
- direct
- groups
- Prior art date
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- 239000000982 direct dye Substances 0.000 title description 10
- 239000000975 dye Substances 0.000 claims abstract description 47
- 239000000118 hair dye Substances 0.000 claims abstract description 30
- 230000001590 oxidative effect Effects 0.000 claims abstract description 5
- 230000002829 reductive effect Effects 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- -1 aromatic nitro compounds Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 238000004043 dyeing Methods 0.000 claims description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003581 cosmetic carrier Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 claims 1
- RLZZZVKAURTHCP-UHFFFAOYSA-N phenanthrene-3,4-diol Chemical compound C1=CC=C2C3=C(O)C(O)=CC=C3C=CC2=C1 RLZZZVKAURTHCP-UHFFFAOYSA-N 0.000 claims 1
- RUKISNQKOIKZGT-UHFFFAOYSA-N 2-nitrodiphenylamine Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=CC=C1 RUKISNQKOIKZGT-UHFFFAOYSA-N 0.000 abstract description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000002453 shampoo Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002243 precursor Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000004040 coloring Methods 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000010902 straw Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- QXYMVUZOGFVPGH-UHFFFAOYSA-N picramic acid Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O QXYMVUZOGFVPGH-UHFFFAOYSA-N 0.000 description 2
- XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- SDICTISQCKLMEB-UHFFFAOYSA-N 1,4-diamino-5-nitroanthracene-9,10-dione Chemical compound O=C1C=2C(N)=CC=C(N)C=2C(=O)C2=C1C=CC=C2[N+]([O-])=O SDICTISQCKLMEB-UHFFFAOYSA-N 0.000 description 1
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 description 1
- ICVRBKCRXNVOJC-UHFFFAOYSA-N 1-amino-4-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2NC ICVRBKCRXNVOJC-UHFFFAOYSA-N 0.000 description 1
- GSLICRAXUQCNOA-UHFFFAOYSA-N 2-(2,4-diamino-3-nitrophenyl)ethanol Chemical compound NC1=CC=C(CCO)C(N)=C1[N+]([O-])=O GSLICRAXUQCNOA-UHFFFAOYSA-N 0.000 description 1
- PIPMXIHACYDRFN-UHFFFAOYSA-N 2-(2,6-diamino-4-nitrophenyl)ethanol Chemical compound NC1=CC([N+]([O-])=O)=CC(N)=C1CCO PIPMXIHACYDRFN-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- QNJWQAYYVNKOKR-UHFFFAOYSA-N 2-(4-amino-2-chloro-5-nitroanilino)ethanol Chemical compound NC1=CC(Cl)=C(NCCO)C=C1[N+]([O-])=O QNJWQAYYVNKOKR-UHFFFAOYSA-N 0.000 description 1
- SCZQUWZLEIYDBD-UHFFFAOYSA-N 2-(4-methyl-2-nitroanilino)ethanol Chemical compound CC1=CC=C(NCCO)C([N+]([O-])=O)=C1 SCZQUWZLEIYDBD-UHFFFAOYSA-N 0.000 description 1
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 1
- WKUXZKMGCVMDDW-UHFFFAOYSA-N 2-[3-amino-4-[bis(2-hydroxyethyl)amino]-2-nitrophenyl]ethanol Chemical compound NC1=C(N(CCO)CCO)C=CC(CCO)=C1[N+]([O-])=O WKUXZKMGCVMDDW-UHFFFAOYSA-N 0.000 description 1
- VIVOYTXGUSBMOP-UHFFFAOYSA-N 2-amino-4-(2-hydroxyethyl)-1-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(CCO)=CC(N)=C2NC VIVOYTXGUSBMOP-UHFFFAOYSA-N 0.000 description 1
- YFKNIPGAJBJZQT-UHFFFAOYSA-N 3-(4-amino-2-chloro-5-nitroanilino)propane-1,2-diol Chemical compound NC1=CC(Cl)=C(NCC(O)CO)C=C1[N+]([O-])=O YFKNIPGAJBJZQT-UHFFFAOYSA-N 0.000 description 1
- VTXBLQLZQLHDIL-UHFFFAOYSA-N 4-(3-hydroxypropylamino)-3-nitrophenol Chemical compound OCCCNC1=CC=C(O)C=C1[N+]([O-])=O VTXBLQLZQLHDIL-UHFFFAOYSA-N 0.000 description 1
- XWNSFEAWWGGSKJ-UHFFFAOYSA-N 4-acetyl-4-methylheptanedinitrile Chemical compound N#CCCC(C)(C(=O)C)CCC#N XWNSFEAWWGGSKJ-UHFFFAOYSA-N 0.000 description 1
- ZVDCYZVYRXZJQF-UHFFFAOYSA-N 6-nitro-1,2,3,4-tetrahydroquinoxaline Chemical compound N1CCNC2=CC([N+](=O)[O-])=CC=C21 ZVDCYZVYRXZJQF-UHFFFAOYSA-N 0.000 description 1
- TWLMSPNQBKSXOP-UHFFFAOYSA-N 6358-09-4 Chemical compound NC1=CC([N+]([O-])=O)=CC(Cl)=C1O TWLMSPNQBKSXOP-UHFFFAOYSA-N 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- JSFUMBWFPQSADC-UHFFFAOYSA-N Disperse Blue 1 Chemical compound O=C1C2=C(N)C=CC(N)=C2C(=O)C2=C1C(N)=CC=C2N JSFUMBWFPQSADC-UHFFFAOYSA-N 0.000 description 1
- GZGZVOLBULPDFD-UHFFFAOYSA-N HC Red No. 3 Chemical compound NC1=CC=C(NCCO)C([N+]([O-])=O)=C1 GZGZVOLBULPDFD-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 239000004153 Potassium bromate Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- ZZTCCAPMZLDHFM-UHFFFAOYSA-N ammonium thioglycolate Chemical compound [NH4+].[O-]C(=O)CS ZZTCCAPMZLDHFM-UHFFFAOYSA-N 0.000 description 1
- 229940075861 ammonium thioglycolate Drugs 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000037308 hair color Effects 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229940094037 potassium bromate Drugs 0.000 description 1
- 235000019396 potassium bromate Nutrition 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229920003170 water-soluble synthetic polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
- A61K2800/432—Direct dyes
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Coloring (AREA)
Abstract
Description
Foreliggende oppfinnelse angår anvendelsen av et direktetrekkende farvestoff med en formel som beskrevet nedenfor sammen med minst et andre direktetrekkende farvestoff med en annen struktur foe å oppnå et hårfarvemiddel som utmerker seg ved en spesielt jevn farvepåtrekking, også på skadet hår. The present invention relates to the use of a direct dye with a formula as described below together with at least one other direct dye with a different structure to obtain a hair dye that is distinguished by a particularly even color application, also on damaged hair.
For farving av hår spiller spesielt, ved siden av oksyda-sjonsfarvene som oppstår ved oksydativ kobling av en eller flere fremkallerkomponenter seg imellom, eller med en eller flere koblerkomponenter, de direktetrekkende hårfarvestoffer en viktig rolle. De direktetrekkende farvestoffer har den fordel at de kan anvendes uten tilsetning av oksydasjons-midler. Som direktetrekkende farvestoff anvendes fortrinnsvis forbindelser som hører til gruppen nitrobenzenderivater. For hair dyeing, in particular, next to the oxidation dyes that occur by oxidative coupling of one or more developer components with each other, or with one or more coupling components, the direct draw hair dyes play an important role. The direct drawing dyes have the advantage that they can be used without the addition of oxidizing agents. Compounds belonging to the group of nitrobenzene derivatives are preferably used as direct draw dyes.
Gode hårfarvemidler må danne de ønskede farvenyanser i tilstrekkelig intensitet. De må ha en god påtrekkingsevne på menneskehår uten å farve hodehuden for sterkt. De derved oppnådde farvinger må oppvise en høy stabilitet mot lys, varme, svette, hårvaskemidler og de kjemikalier som anvendes ved permanentbehandling av håret. Til slutt må de være uten problemer både på det toksikologiske og det dermatologiske området. Dessverre har mange direktetrekkende hårfarvestoffer den mangel at de trekker ujevnt på håret på en slik måte at det sterkere skadede området av hårspissen som regel blir farvet mest intenst enn det yngre og mindre skadede området nærmere hårroten. Av denne grunn er mange av de i og for seg gode farvestoffer uegnet for praktisk anvendelse. Good hair dyes must produce the desired color shades in sufficient intensity. They must have good adhesion to human hair without coloring the scalp too strongly. The dyes thus obtained must show a high stability against light, heat, sweat, hair detergents and the chemicals used in permanent hair treatment. Finally, they must be without problems both in the toxicological and dermatological areas. Unfortunately, many direct hair dyes have the shortcoming that they draw unevenly on the hair in such a way that the more heavily damaged area of the hair tip is usually colored more intensely than the younger and less damaged area closer to the root. For this reason, many of the intrinsically good dyes are unsuitable for practical use.
Det er nu funnet at kombinasjoner av to eller flere direktetrekkende farvestoffer muliggjør en vesentlig jevnere farving også av hår som er skadet ved reduktiv eller oksydativ hårbehandling, for eksempel ved permanentbehandling og bleking, når det i denne kombinasjon foreligger minst et nitrodifenylaminfarvestoff med formel I. It has now been found that combinations of two or more direct dyes enable significantly more uniform coloring also of hair that has been damaged by reductive or oxidative hair treatment, for example by permanent treatment and bleaching, when in this combination there is at least one nitrodiphenylamine dye of formula I.
Gjenstand for foreliggende oppfinnelse er som nevnt inn-ledningsvis anvendelsen av et direktetrekkende farvestoff (A) med formel I The object of the present invention is, as mentioned at the outset, the use of a direct-drawing dye (A) with formula I
der there
R1 og R<2> er hydrogen, C1_4alkylgrupper eller C2_4hydroksy-alkylgrupper og R1 and R<2> are hydrogen, C1-4 alkyl groups or C2-4 hydroxy-alkyl groups and
en av gruppene R<3> til R<7> er en -S03H- eller en COOH-gruppe og de andre er hydrogen, klor, C-^alkylgrupper, C1_4alkoksy-grupper eller grupper med formel -NR<8>R<9> der R^ og R^ er hydrogen, C1_4alkylgrupper, C2_4hydroksyalkylgrupper eller sammen med nitrogenatomet danner en piperidin-, morfolin-, piperazin- eller pyrrolidinring, eller et vannoppløselig salt derav, i hårfarvemidler med et innhold av minst et andre direktetrekkende farvestoff (B) med en annen struktur i en kosmetisk bærer for forbedring av jevnheten av hårfarving, særlig av hår som er beskadiget på grunn av reduktiv eller oksydativ hårbehandling. one of the groups R<3> to R<7> is a -SO3H- or a COOH group and the others are hydrogen, chlorine, C1-4 alkyl groups, C1-4 alkoxy groups or groups of the formula -NR<8>R<9 > where R^ and R^ are hydrogen, C1_4 alkyl groups, C2_4 hydroxyalkyl groups or, together with the nitrogen atom, form a piperidine, morpholine, piperazine or pyrrolidine ring, or a water-soluble salt thereof, in hair dyes containing at least one second direct dye (B) with a different structure in a cosmetic carrier for improving the evenness of hair dyeing, in particular of hair damaged due to reductive or oxidative hair treatment.
Det direktetrekkende farvestoff (A) med formel I er kjent fra EP 0.280.187-Al. På grunn av nærværet av dette farvestoff blir jevnheten av farvepåtrekket av tallrike andre direktetrekkende farvestoff tydelig bedre enn det man skulle vente fra farvepåtrekket av de enkelte farvestoffer for kombinasjonen. I de fleste tilfeller trekker kombinasjonen av farvestoff (A) med formel I og et andre farvestoff (B) jevnere på enhver av komponentene (A) og (B) hver for seg. I det minste ligger imidlertid jevnheten av farvepåtrykket høyere enn det som tilsvarer blandingsregelen. The direct drawing dye (A) of formula I is known from EP 0.280.187-Al. Due to the presence of this dye, the evenness of the color application of numerous other direct dyes is clearly better than what would be expected from the color application of the individual dyes for the combination. In most cases, the combination of dye (A) of formula I and a second dye (B) draws more evenly on any of the components (A) and (B) separately. At least, however, the uniformity of the color impression is higher than that which corresponds to the mixing rule.
Som andre farvestoff (B) kan man anvende direktetrekkende farvestoffer av forskjellig struktur. Særlig foretrukket er direktetrekkende farvestoffer fra gruppen aromatiske nitroforbindelser eller antrakinonforbindelser. Oppfinnelsens virkning med henblikk på forbedret jevnhet av farvepåtrekket ved kombinasjon med farvestoffer med formel I observeres imidlertid også ved andre direktetrekkende farvestoffer, for eksempel ved azofarvestoffer, trifenylmetanfarvestoffer eller indofenoler. As a second dye (B), you can use direct draw dyes of different structure. Particularly preferred are direct dyes from the group of aromatic nitro compounds or anthraquinone compounds. However, the effect of the invention with a view to improved evenness of the dye application when combined with dyes of formula I is also observed with other direct dyes, for example with azo dyes, triphenylmethane dyes or indophenols.
Spesielt egnede direktetrekkende farvestoffer (B) er nevnt i eksempeldelen, særlig i henhold til Bl til B9. Particularly suitable direct drawing dyes (B) are mentioned in the example section, particularly according to B1 to B9.
Spesielt egnede direktetrekkende nitrodifenylaminfarvestoffer Particularly suitable direct drawing nitrodiphenylamine dyes
(A) med formel I er: (A) of formula I is:
Al: 2-nitro-4-aminodifenylamin-2'-karboksylsyre og Al: 2-nitro-4-aminodiphenylamine-2'-carboxylic acid and
A2: 2-nitro-4-amino-4'-dimetylaminodifenylamin-2'-karboksyl syre. A2: 2-nitro-4-amino-4'-dimethylaminodiphenylamine-2'-carboxylic acid.
Ytterligere eksempler kan finnes i EP 0.280.187-A1. Further examples can be found in EP 0.280.187-A1.
De oppnådde hårfarvemidler utmerker seg ved en forbedret vaskekthet. Farvinger som oppnås med en kombinasjon av et nitrodifenylaminf arvestoff (A) med formel I og et andre direktetrekkende farvestoff (B) med en annen struktur blir mindre lyse ved hårvasking enn de som er oppnådd med farvestoff (B) i fravær av et farvestoff med formel I. The obtained hair dyes are distinguished by improved washing fastness. Dyes obtained with a combination of a nitrodiphenylamine dye (A) of formula I and a second direct draw dye (B) with a different structure become less light when washing hair than those obtained with dye (B) in the absence of a dye of formula IN.
Hårfarvemidlene kan også inneholde to forskjellige farvestoffer (A) med formel I og et eller flere ytterligere farvestoffer (B) med en annen struktur. The hair dyes can also contain two different dyes (A) of formula I and one or more additional dyes (B) with a different structure.
Til slutt kan de beskrevne hårfarvemidler også inneholde oksydasj onsfarvetoff-forproduktet. Finally, the described hair dyes can also contain the oxidation dye precursor.
For å fremstille oppfinnelsens hårfarvemidler blir de direktetrekkende hårfarvestoffer (A) med formel I og de ytterligere farvestoffer (B) innarbeidet i en egnet kosmetisk bærer, for eksempel 1 kremer, emulsjoner, geler, eller også tensidholdige, skummende oppløsninger, for eksempel i shampoer, skumaerosoler eller andre tilberedninger som er egnet for anvendelse ved behandling av hår. To produce the hair dyes of the invention, the direct hair dyes (A) with formula I and the additional dyes (B) are incorporated into a suitable cosmetic carrier, for example 1 creams, emulsions, gels, or also surfactant-containing, foaming solutions, for example in shampoos, foam aerosols or other preparations suitable for use in the treatment of hair.
Vanlige bestanddeler i slike kosmetiske tilberedninger er for eksempel fukte- og emulgeringsmidler som anioniske, ikke-ioniske, kationiske, zwitterioniske og amfolyttiske tensider. Foretrukne tensider er for eksempel fettalkoholsulfater, fettalkoholpolyglykoletersulfater, N-alkansulfonater, a-olefinsulfonater, etylenoksydtilleiringsprodukter på fettaminer, på fettsyrer, på fettalkoholer, på alkylfenoler, på fettsyrepartialglycerider, på sorbitanfettsyreestere og på fettsyrealkanolamider. Common ingredients in such cosmetic preparations are, for example, wetting and emulsifying agents such as anionic, non-ionic, cationic, zwitterionic and ampholytic surfactants. Preferred surfactants are, for example, fatty alcohol sulfates, fatty alcohol polyglycol ether sulfates, N-alkane sulfonates, α-olefin sulfonates, ethylene oxide layer products on fatty amines, on fatty acids, on fatty alcohols, on alkylphenols, on fatty acid partial glycerides, on sorbitan fatty acid esters and on fatty acid alkanolamides.
Ytterligere vanlige bestanddeler er vannoppløselige fortykningsmidler som metyl- eller hydroksycellulose, stivelse og vannoppløselige stivelsesderivater, biopolymerer, vannoppløselige syntetiske polymerer og kopolymerer, for eksempel slike av akryl- og metakrylsyre. For formulering som farvekrem anvendes fettkomponenter som fettalkoholer, fettsyrer, fettsyrepartialglycerider, estere, paraffiner og vokser i emulgert form som bærer. Hårfarvemidlene kan ut over dette inneholde kjente hårpleietilsetninger som vannoppløse-lige, kationiske polymerer, vannoppløselige proteiner og proteinderivater, pantotensyre, vitaminer, planteekstrakter samt duftstoffer, pH-regulatorer (bufferstoffer), elektro-lytter og vann. Further common ingredients are water-soluble thickeners such as methyl or hydroxycellulose, starch and water-soluble starch derivatives, biopolymers, water-soluble synthetic polymers and copolymers, for example those of acrylic and methacrylic acid. For formulation as color cream, fatty components such as fatty alcohols, fatty acids, fatty acid partial glycerides, esters, paraffins and waxes in emulsified form are used as a carrier. In addition to this, the hair dyes may contain known hair care additives such as water-soluble, cationic polymers, water-soluble proteins and protein derivatives, pantothenic acid, vitamins, plant extracts as well as fragrances, pH regulators (buffering substances), electrolytes and water.
Bestanddelene i bæreren anvendes ved fremstilling av oppfinnelsens hårfarvemiddel i de vanlige mengder for dette formål, for eksempel anvendes fukte- og emulgeringsmidler i mengder på 0,5 til 5 vekt-# og fortykningsmidler i konsentra-sjoner på 0,1 til 10 vekt-# av det totale farvestoff. The components in the carrier are used in the production of the hair dye of the invention in the usual amounts for this purpose, for example wetting and emulsifying agents are used in amounts of 0.5 to 5 weight-# and thickening agents in concentrations of 0.1 to 10 weight-# of the total dye.
I en foretrukket utførelsesform er bæreren en emulsjon med et innhold av 1 til 5 vekt-# av en Ci2-22^e'ttal^onol» 5 til 20 vekt-# av et tilleiringsprodukt av 5 til 20 mol etylenoksyd på et mol av et rett, endestående Ci2_22alkylamin, a-'-t beregnet på vekten av det totale hårfarvemiddel. In a preferred embodiment, the carrier is an emulsion with a content of 1 to 5 wt-# of a Ci2-22^e'tal^onol» 5 to 20 wt-# of an addition product of 5 to 20 moles of ethylene oxide on one mole of a straight, terminal C12-22alkylamine, a-'-t calculated on the weight of the total hair dye.
I oppfinnelsens hårfarvemidler anvendes de direktetrekkende hårf arvestof f er (A + B) totalt i en mengde på 0,05 til 5 vekt-#, fortrinnsvis 0,1 til 2 vekt-%, beregnet på det totale hårfarvemiddel. Derved kan mengdeforholdet farvestoff (A) med formel I: Farvestoff (B) med en annen struktur, ligge i området 1:9 til 9:1 og fortrinnsvis i området 3:7 til 7:3. In the hair dyes of the invention, the direct hair dyes (A + B) are used in total in an amount of 0.05 to 5% by weight, preferably 0.1 to 2% by weight, calculated on the total hair dye. Thereby, the quantity ratio dye (A) with formula I: dye (B) with a different structure can lie in the range 1:9 to 9:1 and preferably in the range 3:7 to 7:3.
Når det oppnådde hårfarvemiddel inneholder oksydasjons-farvestoff forprodukter er det i tillegg å anbefale å tilsette en liten mengde av et reduksjonsmiddel, for eksempel 0,5 til 2,0 vekt-# natriumsulf it, for å stabilisere oksyda-sjonsfarvestoff forproduktene. I dette tilfellet tilsetter man før anvendelsen av hårfarvemidlet et oksydasjonsmiddel for å innlede den oksydataive utvikling av oksydasjons-farvestoff forproduktet. Som oksydasjonsmiddel kan man særlig benytte hydrogenperoksyd eller dettes tilleiringsprodukt på urinstoff, melamin eller natriumborat samt blandinger av slike hydrogenperoksydtilleiringsprodukter med kaliumperoksyd i sulfat. When the obtained hair dye contains oxidation dye precursors, it is additionally recommended to add a small amount of a reducing agent, for example 0.5 to 2.0 wt% sodium sulphite, to stabilize the oxidation dye precursors. In this case, before the application of the hair dye, an oxidizing agent is added to initiate the oxidative development of the oxidation dye precursor. As an oxidizing agent, you can particularly use hydrogen peroxide or its deposition product on urea, melamine or sodium borate as well as mixtures of such hydrogen peroxide deposition products with potassium peroxide in sulfate.
Anvendelsen av det oppnådde hårfarvemiddel kan, uavhengig av type kosmetisk tilberedning, for eksempel som krem, gel eller shampo, skje i svakt surt, nøytralt eller alkalisk medium. Foretrukket er anvendelsen av hårfarvemidlet i et pH-område fra 6 til 10. Anvendelsestemperaturen kan ligge i området 15 og 40°C. Efter en innvirkningstid på ca. 30 minutter fjernes hårfarvemidler ved skylling av håret som skal farves. Derefter eftervaskes håret med en mild shampo og tørkes. Eftervaskingen med en shampo faller bort når det anvendes en bærer med høyt tensidinnhold, for eksempel en farveshampo. The application of the obtained hair dye can, regardless of the type of cosmetic preparation, for example as a cream, gel or shampoo, take place in a slightly acidic, neutral or alkaline medium. The use of the hair dye in a pH range from 6 to 10 is preferred. The application temperature can be in the range of 15 and 40°C. After an impact time of approx. After 30 minutes, hair dyes are removed by rinsing the hair to be dyed. The hair is then washed with a mild shampoo and dried. After-washing with a shampoo is omitted when a carrier with a high surfactant content is used, for example a colored shampoo.
Med de oppnådde hårfarvemidler kan man oppnå hårfarvinger med høy intensitet og gode ekthetsegenskaper, særlig også med god vaskeekthet og høy stabilitet mot "blødning" og farve-forandringer ved shamponering. De efterfølgende eksempler skal forklare oppfinnelsen nærmere uten å begrense den. With the obtained hair dyes, hair dyes with high intensity and good authenticity properties can be achieved, especially also with good washing fastness and high stability against "bleeding" and color changes during shampooing. The following examples shall explain the invention in more detail without limiting it.
Eksempler Examples
1. Forbedring av egaliseringsevnen 1. Improvement of the equalization ability
1.1 Fremstilling av farvetilberedningen 1.1 Preparation of the color preparation
Det ble fremstilt et hårfarvemiddel med følgende sammen-setning: A hair dye with the following composition was produced:
Som direktetrekker med formel I anvendes: As a direct draw with formula I is used:
Al: 2-nitro-4-amino-2'-karboksydifenylamin Al: 2-nitro-4-amino-2'-carboxydiphenylamine
A2: 2-nitro-4-amino-2'-karboksy-4'-dimetyl-amino-difenylamin. A2: 2-nitro-4-amino-2'-carboxy-4'-dimethyl-amino-diphenylamine.
Som ytterligere direktetrekker anvendes: As an additional direct draw, the following are used:
Bl: 1,2 ,3,4-tetrahydro-6-nitrokinoksalin Bl: 1,2,3,4-tetrahydro-6-nitroquinoxaline
B2: pikraminsyre (2-amino-4,6-dinitrofenol) B2: picramic acid (2-amino-4,6-dinitrophenol)
B3: l-amino-2-nitro-4-(2,3-dihydroksypropylamino)-5-klor benzen B3: 1-amino-2-nitro-4-(2,3-dihydroxypropylamino)-5-chlorobenzene
B4: l-amino-2-nitro-4(2-hydroksyetylamino)-5-klorbenzen B4: 1-amino-2-nitro-4(2-hydroxyethylamino)-5-chlorobenzene
B5: 1,4-bis-(p<->hydroksyetylamino)-2-nitrobenzen B5: 1,4-bis-(p<->hydroxyethylamino)-2-nitrobenzene
B6: 4-(3-hydroksypropyl)amino-3-nitrofenol B6: 4-(3-hydroxypropyl)amino-3-nitrophenol
B7: l-(2-hydroksyetyl)amino-4-metyl-2-nitrobenzen B7: 1-(2-hydroxyethyl)amino-4-methyl-2-nitrobenzene
B8: 6-klor-4-nitro-2-aminofenol B8: 6-chloro-4-nitro-2-aminophenol
B9: l-(2-hydroksyetyl)-amino-2-nitro-4-bis-(2-hydroksy-etyl )aminobenzen B9: 1-(2-hydroxyethyl)-amino-2-nitro-4-bis-(2-hydroxy-ethyl)aminobenzene
B10: l-(2-hydroksyetyl-)amino-2-nitro-4-aminobenzen B10: 1-(2-hydroxyethyl)amino-2-nitro-4-aminobenzene
Bli: 2-nltro-p-fenylendiamin Become: 2-nltro-p-phenylenediamine
B12: l-amino-2-nitro-4-bis-(2-hydroksyetyl)-aminobenzen B13: 2-amino-4-nitrofenol B12: 1-amino-2-nitro-4-bis-(2-hydroxyethyl)-aminobenzene B13: 2-amino-4-nitrophenol
B14: l-amino-2-(2-hydroksyetyl)-amino-5-nitrobenzen B15: l-amino-2-nitro-4-(2-hydroksyetyl)-aminobenzen B16: 1,4,5,8-tetraamino-antraklnon B14: 1-amino-2-(2-hydroxyethyl)-amino-5-nitrobenzene B15: 1-amino-2-nitro-4-(2-hydroxyethyl)-aminobenzene B16: 1,4,5,8-tetraamino- anthraquinone
B17: l-amino-4-metylamino-antrakinon B17: 1-amino-4-methylamino-anthraquinone
B18: 1,4-diamino-5-nitro-antrakinon B18: 1,4-diamino-5-nitro-anthraquinone
B19: l-metylamino-4-(2-hydroksyetyl)-amino-antraklnon B19: 1-methylamino-4-(2-hydroxyethyl)-amino-anthraquinone
B20: 1,4-diaminoantrakinon B20: 1,4-diaminoanthraquinone
B21: l-(4'-bis-(2-hydroksyetyl)-amino)-fenylazo-4'amino benzol. B21: 1-(4'-bis-(2-hydroxyethyl)-amino)-phenylazo-4'-amino benzene.
1.2. Hårfarving 1.2. Hair dyeing
Gråe hårbunter med 2 g vekt og en lengde på 16 til 18 cm behandles i hårspissområdet (øvre halvdel) med et koldbølge-middel (vandig oppløsning av ammoniumtioglykolat) i 30 minutter ved 37°C, skylles med varmt vann, behandles derefter med 10 ml av en fikseringsoppløsning (kaliumbromatoppløsning) og skylles igjen. Derefter blir den samme halvpart blondert med en vandig tilberedning av hydrogenperoksyd og ammonium-peroksydisulfat ved 27°C i 30 minutter. Derefter fulgte nok en gang behandlingen med koldbølgemiddelet og fikserings-oppløsningen. Til slutt ble hele hårbunten blondert en gang til. På denne måte oppnådde man to forskjellig strabaserte områder, et sterkt strabasert hårspissområde og et mindre strabasert hårrotområde. Gray hair bundles weighing 2 g and 16 to 18 cm in length are treated in the tip area (upper half) with a cold wave agent (aqueous solution of ammonium thioglycolate) for 30 minutes at 37°C, rinsed with warm water, then treated with 10 ml of a fixing solution (potassium bromate solution) and rinsed again. The same half is then bleached with an aqueous preparation of hydrogen peroxide and ammonium peroxydisulphate at 27°C for 30 minutes. Then followed once again the treatment with the cold wave agent and the fixing solution. Finally, the whole bundle of hair was braided once more. In this way, two different straw-based areas were obtained, a strongly straw-based hair tip area and a less straw-based hair root area.
De på denne måte forbehandlede hårbunter ble farvet med hårfarvemidlet ifølge 1.1 overfor hvorved man som direktetrekker anvendte de i tabell I angitte farvestoffer eller farvestoffkombinasjoner. Farveoppløsningene ble beholdt på hårbuntene i ca. 20 minutter ved 27° C, så vasket ut med et vanlig hårvaskemiddel, skyllet med vann og tørket. The bundles of hair pre-treated in this way were dyed with the hair dye according to 1.1 above, whereby the dyes or dye combinations specified in Table I were used as a direct dye. The dye solutions were kept on the hair bundles for approx. 20 minutes at 27° C, then washed out with a normal hair detergent, rinsed with water and dried.
1.3. Bedømmmelse av jevnheten av hårfarvingen (farveavstands-verdier (DE) mellom hårspiss og hårrot). 1.3. Assessment of the evenness of the hair coloring (color distance values (DE) between hair tip and hair root).
Hver hårbunt ble målt på 8 steder (4 i området hårroten og 4 i området hårsplssen) ved hjelp av et farvemålesystem fra firma Datacolor. Derved ble prøven som skulle undersøkes fiksert i en innspenningsinnretning i et spektralfotometer og remisjonsverdiene målt over området for det synlige lys på 390 til 700 nm i avstander til 10 nm og de oppnådde verdier ble bearbeidet med en kalkulator (Minicomputer HP 2113 E). Regneprogrammet ga normfarveverdiene i henhold til det til ClE-systemet (Comission International de l'Eclairage) svarende DIN 5033 og regnet om i farveavstandstall i henhold til DIN 6174. Each bundle of hair was measured in 8 places (4 in the area of the hair root and 4 in the area of the hair split) using a color measuring system from the company Datacolor. Thereby, the sample to be examined was fixed in a clamping device in a spectral photometer and the remission values were measured over the visible light range of 390 to 700 nm at distances of 10 nm and the values obtained were processed with a calculator (Minicomputer HP 2113 E). The calculation program gave the standard color values according to that of the ClE system (Commission International de l'Eclairage) corresponding to DIN 5033 and converted into color distance numbers according to DIN 6174.
I tabell I gjengis farveavstandsverdiene (DE) for utfarvinger med enkelte farvestoffer og med oppfinnelsens farvestoffkombinasjoner. Farveavstandene for utfarvingene med oppfinnelsens farvekombinasjoner (direktetrekkere type A + type B) er også gjengitt i tabellen. Table I gives the color distance values (DE) for dyeing with individual dyes and with the dye combinations of the invention. The color distances for the colorings with the color combinations of the invention (direct draw type A + type B) are also reproduced in the table.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4110995A DE4110995A1 (en) | 1991-04-05 | 1991-04-05 | HAIR DRYER WITH DIRECT DYES |
| PCT/EP1992/000681 WO1992017156A1 (en) | 1991-04-05 | 1992-03-27 | Hair colourants with direct dyes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO932907D0 NO932907D0 (en) | 1993-08-16 |
| NO932907L NO932907L (en) | 1993-08-16 |
| NO300953B1 true NO300953B1 (en) | 1997-08-25 |
Family
ID=6428867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO932907A NO300953B1 (en) | 1991-04-05 | 1993-08-16 | Use of a direct-dye with at least one other direct-dye |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0578665B1 (en) |
| JP (1) | JPH06505984A (en) |
| KR (1) | KR100204550B1 (en) |
| AT (1) | ATE115853T1 (en) |
| CA (1) | CA2107796A1 (en) |
| DE (2) | DE4110995A1 (en) |
| DK (1) | DK0578665T3 (en) |
| ES (1) | ES2066609T3 (en) |
| FI (1) | FI104043B1 (en) |
| NO (1) | NO300953B1 (en) |
| PL (1) | PL170028B1 (en) |
| WO (1) | WO1992017156A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10042786C2 (en) * | 2000-08-31 | 2002-10-24 | Wella Ag | N-heteroarylmethyl-p-phenylenediamine derivatives and hair dyes containing these compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3537763A1 (en) * | 1985-10-24 | 1987-04-30 | Henkel Kgaa | HAIR DYE WITH DIRECT DRAWING NITRODIPHENYLAMINE DERIVATIVES |
| DE3706225A1 (en) * | 1987-02-26 | 1988-09-08 | Henkel Kgaa | HAIR DYE WITH DIRECT DRAWING NITRODIPHENYLAMINE DERIVATIVES |
-
1991
- 1991-04-05 DE DE4110995A patent/DE4110995A1/en not_active Withdrawn
-
1992
- 1992-03-27 CA CA002107796A patent/CA2107796A1/en not_active Abandoned
- 1992-03-27 PL PL92300775A patent/PL170028B1/en unknown
- 1992-03-27 KR KR1019930702984A patent/KR100204550B1/en not_active IP Right Cessation
- 1992-03-27 ES ES92907054T patent/ES2066609T3/en not_active Expired - Lifetime
- 1992-03-27 AT AT92907054T patent/ATE115853T1/en not_active IP Right Cessation
- 1992-03-27 DK DK92907054.8T patent/DK0578665T3/en active
- 1992-03-27 DE DE59201029T patent/DE59201029D1/en not_active Expired - Lifetime
- 1992-03-27 JP JP4506720A patent/JPH06505984A/en active Pending
- 1992-03-27 EP EP92907054A patent/EP0578665B1/en not_active Expired - Lifetime
- 1992-03-27 WO PCT/EP1992/000681 patent/WO1992017156A1/en active IP Right Grant
-
1993
- 1993-08-16 NO NO932907A patent/NO300953B1/en unknown
- 1993-10-01 FI FI934334A patent/FI104043B1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| WO1992017156A1 (en) | 1992-10-15 |
| FI104043B (en) | 1999-11-15 |
| NO932907D0 (en) | 1993-08-16 |
| FI104043B1 (en) | 1999-11-15 |
| EP0578665B1 (en) | 1994-12-21 |
| ATE115853T1 (en) | 1995-01-15 |
| CA2107796A1 (en) | 1992-10-06 |
| NO932907L (en) | 1993-08-16 |
| FI934334A (en) | 1993-10-01 |
| DK0578665T3 (en) | 1995-05-29 |
| EP0578665A1 (en) | 1994-01-19 |
| JPH06505984A (en) | 1994-07-07 |
| FI934334A0 (en) | 1993-10-01 |
| PL170028B1 (en) | 1996-10-31 |
| ES2066609T3 (en) | 1995-03-01 |
| DE4110995A1 (en) | 1992-10-08 |
| DE59201029D1 (en) | 1995-02-02 |
| KR100204550B1 (en) | 1999-06-15 |
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