CN101384303A - 用于角蛋白纤维的着色剂 - Google Patents
用于角蛋白纤维的着色剂 Download PDFInfo
- Publication number
- CN101384303A CN101384303A CNA200780005873XA CN200780005873A CN101384303A CN 101384303 A CN101384303 A CN 101384303A CN A200780005873X A CNA200780005873X A CN A200780005873XA CN 200780005873 A CN200780005873 A CN 200780005873A CN 101384303 A CN101384303 A CN 101384303A
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- CN
- China
- Prior art keywords
- alkyl
- amino
- phenyl
- ethyl
- unsubstituted
- 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.)
- Granted
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- 239000000835 fiber Substances 0.000 title claims abstract description 19
- 102000011782 Keratins Human genes 0.000 title claims abstract description 16
- 108010076876 Keratins Proteins 0.000 title claims abstract description 16
- 238000004040 coloring Methods 0.000 title claims abstract description 13
- 239000003086 colorant Substances 0.000 title claims description 38
- 239000000987 azo dye Substances 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 136
- -1 N-R6 Chemical compound 0.000 claims description 103
- 125000000217 alkyl group Chemical group 0.000 claims description 79
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 64
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 43
- 239000007800 oxidant agent Substances 0.000 claims description 36
- 239000000975 dye Substances 0.000 claims description 32
- 230000001590 oxidative effect Effects 0.000 claims description 32
- 229920006395 saturated elastomer Chemical group 0.000 claims description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 27
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 24
- 239000003153 chemical reaction reagent Substances 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 239000000118 hair dye Substances 0.000 claims description 15
- 230000003647 oxidation Effects 0.000 claims description 15
- 238000007254 oxidation reaction Methods 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 14
- 239000011593 sulfur Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 150000002431 hydrogen Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000002837 carbocyclic group Chemical group 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 239000002243 precursor Substances 0.000 claims description 8
- PNWSHHILERSSLF-UHFFFAOYSA-N 4-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC=C(C(O)=O)C=C1C(O)=O PNWSHHILERSSLF-UHFFFAOYSA-N 0.000 claims description 6
- AYDQIZKZTQHYIY-UHFFFAOYSA-N OC(=O)C1(C)CC(C(O)=O)=CC=C1 Chemical compound OC(=O)C1(C)CC(C(O)=O)=CC=C1 AYDQIZKZTQHYIY-UHFFFAOYSA-N 0.000 claims description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 6
- 239000000982 direct dye Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 229910021538 borax Inorganic materials 0.000 claims description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 3
- 235000010339 sodium tetraborate Nutrition 0.000 claims description 3
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 claims description 3
- MDSIYMGUKYDHAS-UHFFFAOYSA-M 2-[4-[(4,6-dinitro-1,3-benzothiazol-2-yl)diazenyl]-n-ethylanilino]ethyl-trimethylazanium;bromide Chemical compound [Br-].C1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=NC2=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C2S1 MDSIYMGUKYDHAS-UHFFFAOYSA-M 0.000 claims description 2
- ZXPLDCQCYBDZMA-UHFFFAOYSA-M 2-[4-[(5,6-dinitro-1,3-benzothiazol-2-yl)diazenyl]-n-ethylanilino]ethyl-trimethylazanium;bromide Chemical compound [Br-].C1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=NC2=CC([N+]([O-])=O)=C([N+]([O-])=O)C=C2S1 ZXPLDCQCYBDZMA-UHFFFAOYSA-M 0.000 claims description 2
- 239000001000 anthraquinone dye Substances 0.000 claims description 2
- 239000001005 nitro dye Substances 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 210000004209 hair Anatomy 0.000 description 41
- 239000000203 mixture Substances 0.000 description 38
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 238000005406 washing Methods 0.000 description 16
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 229940123457 Free radical scavenger Drugs 0.000 description 13
- 239000002516 radical scavenger Substances 0.000 description 13
- 229910021529 ammonia Inorganic materials 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 229960002163 hydrogen peroxide Drugs 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000002453 shampoo Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 6
- 241000972773 Aulopiformes Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000001099 ammonium carbonate Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 235000019515 salmon Nutrition 0.000 description 6
- 238000009827 uniform distribution Methods 0.000 description 6
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 5
- MHOFGBJTSNWTDT-UHFFFAOYSA-M 2-[n-ethyl-4-[(6-methoxy-3-methyl-1,3-benzothiazol-3-ium-2-yl)diazenyl]anilino]ethanol;methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC(N(CCO)CC)=CC=C1N=NC1=[N+](C)C2=CC=C(OC)C=C2S1 MHOFGBJTSNWTDT-UHFFFAOYSA-M 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- ULIPQUITJRPDOM-UHFFFAOYSA-M 2-[4-[(4,5-dimethyl-1,3-thiazol-2-yl)diazenyl]-n-ethylanilino]ethyl-trimethylazanium;bromide Chemical compound [Br-].C1=CC(N(CC[N+](C)(C)C)CC)=CC=C1N=NC1=NC(C)=C(C)S1 ULIPQUITJRPDOM-UHFFFAOYSA-M 0.000 description 4
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
- JDRSMPFHFNXQRB-CMTNHCDUSA-N Decyl beta-D-threo-hexopyranoside Chemical compound CCCCCCCCCCO[C@@H]1O[C@H](CO)C(O)[C@H](O)C1O JDRSMPFHFNXQRB-CMTNHCDUSA-N 0.000 description 4
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 4
- OVBJJZOQPCKUOR-UHFFFAOYSA-L EDTA disodium salt dihydrate Chemical compound O.O.[Na+].[Na+].[O-]C(=O)C[NH+](CC([O-])=O)CC[NH+](CC([O-])=O)CC([O-])=O OVBJJZOQPCKUOR-UHFFFAOYSA-L 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- UXEAWNJALIUYRH-UHFFFAOYSA-N [8-[(4-aminophenyl)hydrazinylidene]-7-oxonaphthalen-2-yl]-trimethylazanium;chloride Chemical compound [Cl-].C12=CC([N+](C)(C)C)=CC=C2C=CC(=O)\C1=N/NC1=CC=C(N)C=C1 UXEAWNJALIUYRH-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000004061 bleaching Methods 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 4
- 229940073499 decyl glucoside Drugs 0.000 description 4
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 4
- FPVGTPBMTFTMRT-UHFFFAOYSA-L disodium;2-amino-5-[(4-sulfonatophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-UHFFFAOYSA-L 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 235000019233 fast yellow AB Nutrition 0.000 description 4
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 4
- 125000005208 trialkylammonium group Chemical group 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 3
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 229920001661 Chitosan Polymers 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- CQPFMGBJSMSXLP-UHFFFAOYSA-M acid orange 7 Chemical compound [Na+].OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 CQPFMGBJSMSXLP-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 3
- 235000012501 ammonium carbonate Nutrition 0.000 description 3
- 238000006149 azo coupling reaction Methods 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- ONTQJDKFANPPKK-UHFFFAOYSA-L chembl3185981 Chemical compound [Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C=C1N=NC1=CC(S([O-])(=O)=O)=C(C=CC=C2)C2=C1O ONTQJDKFANPPKK-UHFFFAOYSA-L 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 description 3
- 238000007046 ethoxylation reaction Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 229920005615 natural polymer Polymers 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- YOWAEZWWQFSEJD-UHFFFAOYSA-N quinoxalin-2-amine Chemical compound C1=CC=CC2=NC(N)=CN=C21 YOWAEZWWQFSEJD-UHFFFAOYSA-N 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- AXMCIYLNKNGNOT-UHFFFAOYSA-N sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-N 0.000 description 3
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 3
- JUUXYSDWEGIGHM-UHFFFAOYSA-N (4-nitrophenyl)diazene Chemical group [O-][N+](=O)C1=CC=C(N=N)C=C1 JUUXYSDWEGIGHM-UHFFFAOYSA-N 0.000 description 2
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- AQXYVFBSOOBBQV-UHFFFAOYSA-N 1-amino-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2N AQXYVFBSOOBBQV-UHFFFAOYSA-N 0.000 description 2
- YUNHBAIHRNIODP-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-5-nitrophenol Chemical compound OCCNC1=CC=C([N+]([O-])=O)C=C1O YUNHBAIHRNIODP-UHFFFAOYSA-N 0.000 description 2
- LFOUYKNCQNVIGI-UHFFFAOYSA-N 2-(2-nitroanilino)ethanol Chemical compound OCCNC1=CC=CC=C1[N+]([O-])=O LFOUYKNCQNVIGI-UHFFFAOYSA-N 0.000 description 2
- LGZSBRSLVPLNTM-UHFFFAOYSA-N 2-(4-amino-2-methyl-5-nitroanilino)ethanol Chemical compound CC1=CC(N)=C([N+]([O-])=O)C=C1NCCO LGZSBRSLVPLNTM-UHFFFAOYSA-N 0.000 description 2
- LGGKGPQFSCBUOR-UHFFFAOYSA-N 2-(4-chloro-2-nitroanilino)ethanol Chemical compound OCCNC1=CC=C(Cl)C=C1[N+]([O-])=O LGGKGPQFSCBUOR-UHFFFAOYSA-N 0.000 description 2
- WXGKXLXGYOYZMX-UHFFFAOYSA-N 2-[4-(2-aminoethylamino)-3-nitrophenoxy]ethanol Chemical compound NCCNC1=CC=C(OCCO)C=C1[N+]([O-])=O WXGKXLXGYOYZMX-UHFFFAOYSA-N 0.000 description 2
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- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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- 235000011181 potassium carbonates Nutrition 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- DWSGLSZEOZQMSP-UHFFFAOYSA-N potassium;sodium Chemical compound [Na+].[K+] DWSGLSZEOZQMSP-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- WDFVICOGUPEJEQ-UHFFFAOYSA-N pyrazol-3-one;hydrochloride Chemical compound Cl.O=C1C=CN=N1 WDFVICOGUPEJEQ-UHFFFAOYSA-N 0.000 description 1
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 229940051201 quinoline yellow Drugs 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
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- COEZWFYORILMOM-UHFFFAOYSA-M sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-M 0.000 description 1
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- DJDYMAHXZBQZKH-UHFFFAOYSA-M sodium;1-amino-4-(cyclohexylamino)-9,10-dioxoanthracene-2-sulfonate Chemical compound [Na+].C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S([O-])(=O)=O)C=C1NC1CCCCC1 DJDYMAHXZBQZKH-UHFFFAOYSA-M 0.000 description 1
- GTKIEPUIFBBXJQ-UHFFFAOYSA-M sodium;2-[(4-hydroxy-9,10-dioxoanthracen-1-yl)amino]-5-methylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O GTKIEPUIFBBXJQ-UHFFFAOYSA-M 0.000 description 1
- VRDAELYOGRCZQD-NFLRKZIHSA-M sodium;4-[(2z)-2-[(5e)-5-[(2,4-dimethylphenyl)hydrazinylidene]-4,6-dioxocyclohex-2-en-1-ylidene]hydrazinyl]benzenesulfonate Chemical compound [Na+].CC1=CC(C)=CC=C1N\N=C(/C(=O)C=C\1)C(=O)C/1=N\NC1=CC=C(S([O-])(=O)=O)C=C1 VRDAELYOGRCZQD-NFLRKZIHSA-M 0.000 description 1
- MLVYOYVMOZFHIU-UHFFFAOYSA-M sodium;4-[(4-anilinophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(S(=O)(=O)[O-])=CC=C1N=NC(C=C1)=CC=C1NC1=CC=CC=C1 MLVYOYVMOZFHIU-UHFFFAOYSA-M 0.000 description 1
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
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- 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
- IYBVSTPLAWCNJD-UHFFFAOYSA-K trisodium 1H-pyrazole-5-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)c1ccn[nH]1.[O-]C(=O)c1ccn[nH]1.[O-]C(=O)c1ccn[nH]1 IYBVSTPLAWCNJD-UHFFFAOYSA-K 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- AODQPPLFAXTBJS-UHFFFAOYSA-M victoria blue 4R Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C(C=C1)C2=CC=CC=C2C1=[N+](C)C1=CC=CC=C1 AODQPPLFAXTBJS-UHFFFAOYSA-M 0.000 description 1
- LLWJPGAKXJBKKA-UHFFFAOYSA-N victoria blue B Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C(C=C1)C2=CC=CC=C2C1=[NH+]C1=CC=CC=C1 LLWJPGAKXJBKKA-UHFFFAOYSA-N 0.000 description 1
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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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- 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
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- 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
- A61K8/496—Triazoles or their condensed derivatives, e.g. benzotriazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
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Abstract
Description
实例 | 式(I)的化合物(如实例1a至1c中) | 着色剂的pH | 着色后的色调 | 颜色测定值着色后 |
- | 着色处理前毛发的色调 | --- | --- | L=80.60C=12.10h=92.10 |
2 | 2-[{4-[(4,5-二甲基-1,3-噻唑-2-基)二氮烯基]苯基}(乙基)氨基]-N,N,N-三甲基乙基溴化铵(1a) | 9.6 | 桔红色 | L=40.93C=68.59h=37.3 |
3 | 2-[{4-[(4,5-二甲基-1,3-噻唑-2-基)二氮烯基]-3-甲基苯基}-(乙基)氨 | 9.5 | 红色 | L=38.13C=65.52 |
基]-N,N,N-三甲基乙基溴化铵(1b) | h=34.8 | |||
4 | 2-[{3-氯-4-[(4,5-二甲基-1,3-噻唑-2-基)二氮烯基]-苯基}(乙基)氨基]-N,N,N-三甲基乙基铵甲酯硫酸根(1c) | 9.4 | 桔红色 | L=45.72C=70.63h=42.3 |
实例 | 式(I)的化合物(如实例1a至1c中) | 着色剂的pH | 着色后的色调 | 颜色测量值着色后 |
- | 着色处理前毛发的色调 | --- | --- | L=80.60C=12.10h=92.10 |
5 | 2-[{4-[(4,5-二甲基-1,3-噻唑-2-基)二氮烯基]苯基}(乙基)氨基]-N,N,N-三甲基乙基溴化铵(1a) | 9.0 | 桔红色 | L=44.96C=72.13h=40.1 |
6 | 2-[{4-[(4,5-二甲基-1,3-噻唑-2-基)二 | 9.2 | 红色 | L=41.08 |
氮烯基]-3-甲基苯基}-(乙基)氨基]-N,N,N-三甲基乙基溴化铵(1b) | C=67.76h=36.00 | |||
7 | 2-[{3-氯-4-[(4,5-二甲基-1,3-噻唑-2-基)二氮烯基]-苯基}(乙基)氨基]-N,N,N-三甲基乙基铵甲酯硫酸根(1c) | 9.4 | 桔红色 | L=45.99C=72.11h=40.9 |
实例 | 具有式(I)的化合物 | 着色剂的pH | 着色后的色调 | 洗涤后的色调 |
8 | 2-[{4-[(4,5-二甲基-1,3-噻唑-2-基)二氮烯基]苯基}-(乙基)氨基]-N,N,N-三甲基乙基溴化铵(1a) | 9.4 | 红褐色L=27.03C=23.11h=42.7 | 红褐色L=29.48C=23.11h=47.1 |
实例 | 具有式(I)的化合物 | 着色剂的pH | 着色后的色调 | 洗涤后的色调 |
9 | 2-[{4-[(4,5-二甲基-1,3-噻唑-2-基)二氮烯基]苯基}-(乙基)氨基]-N,N,N-三甲基乙基溴化铵(1a) | 9.4 | 橙褐色L=30.16C=26.83h=46.2 | 橙褐色L=32.60C=25.69h=51.0 |
Claims (11)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06003343.8 | 2006-02-18 | ||
EP06003343A EP1820536B1 (en) | 2006-02-18 | 2006-02-18 | Coloring agents for keratin fibers |
PCT/IB2007/050428 WO2007093943A1 (en) | 2006-02-18 | 2007-02-09 | Coloring agents for keratin fibers |
Publications (2)
Publication Number | Publication Date |
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CN101384303A true CN101384303A (zh) | 2009-03-11 |
CN101384303B CN101384303B (zh) | 2012-07-04 |
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Application Number | Title | Priority Date | Filing Date |
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CN200780005873XA Expired - Fee Related CN101384303B (zh) | 2006-02-18 | 2007-02-09 | 用于角蛋白纤维的着色剂 |
Country Status (7)
Country | Link |
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US (2) | US7513917B2 (zh) |
EP (1) | EP1820536B1 (zh) |
JP (1) | JP5431735B2 (zh) |
CN (1) | CN101384303B (zh) |
AT (1) | ATE536915T1 (zh) |
MX (1) | MX2008010403A (zh) |
WO (1) | WO2007093943A1 (zh) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
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ATE536915T1 (de) * | 2006-02-18 | 2011-12-15 | Wella GmbH | Mittel zum färben von keratinhaltigen fasern |
US8609074B2 (en) * | 2011-12-30 | 2013-12-17 | L'oreal | Methods for making up a keratinous substrate |
US9913791B2 (en) | 2015-03-19 | 2018-03-13 | Noxell Corporation | Method for improving acid perspiration resistance of fluorescent compounds on hair |
WO2016146813A1 (en) * | 2015-03-19 | 2016-09-22 | Basf Se | Cationic direct dyes |
WO2016149430A1 (en) | 2015-03-19 | 2016-09-22 | The Procter & Gamble Company | Compositions for dyeing hair with cationic direct dyes |
US9839593B2 (en) | 2015-03-19 | 2017-12-12 | Noxell Corporation | Method of coloring hair with direct dye compounds |
CN107635536A (zh) | 2015-03-19 | 2018-01-26 | 诺赛尔股份有限公司 | 使用直接染料化合物染色毛发的方法 |
US9839592B2 (en) | 2015-03-19 | 2017-12-12 | Noxell Corporation | Fluorescent compounds for treating hair |
US9872823B2 (en) | 2015-03-19 | 2018-01-23 | Noxell Corporation | Method for improving fastness properties of fluorescent compounds on hair |
WO2016149429A1 (en) | 2015-03-19 | 2016-09-22 | The Procter & Gamble Company | Compositions for dyeing hair with cationic direct dyes |
US9943472B2 (en) | 2015-03-19 | 2018-04-17 | Noxell Corporation | Acid perspiration resistant fluorescent compounds for treating hair |
US9982138B2 (en) | 2016-09-13 | 2018-05-29 | Noxell Corporation | Hair color compositions comprising stable violet-blue to blue imidazolium dyes |
US10034823B2 (en) | 2016-09-16 | 2018-07-31 | Noxell Corporation | Method of coloring hair with washfast blue imidazolium direct dye compounds |
US9918919B1 (en) | 2016-09-16 | 2018-03-20 | Noxell Corporation | Method of coloring hair with washfast yellow imidazolium direct dye compounds |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1162665A (en) * | 1966-09-27 | 1969-08-27 | Du Pont | Cationic and Basic Benzothiazolylazo Dyes, their preparation and use |
LU53050A1 (zh) * | 1967-02-22 | 1968-08-27 | ||
DE3101140A1 (de) | 1981-01-16 | 1982-09-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von loesungen kationischer azofarbstoffe |
EP0514336B1 (de) * | 1991-05-17 | 1996-12-11 | Ciba-Geigy Ag | Verfahren zur Herstellung hochkonzentrierter wässriger Lösungen von kationischen Azofarbstoffen |
DE4322211A1 (de) | 1993-07-03 | 1995-01-12 | Basf Ag | Wäßrige, mehrphasige, stabile Fertigformulierung für Pflanzenschutz-Wirkstoffe und Verfahren zu ihrer Herstellung |
FR2741798B1 (fr) | 1995-12-01 | 1998-01-09 | Oreal | Composition de teinture eclaircissante pour fibres keratiniques comprenant un colorant direct specifique |
DE19618595A1 (de) | 1996-05-09 | 1997-11-13 | Wella Ag | Färbemittel |
DE19835575A1 (de) * | 1998-08-06 | 2000-03-02 | Mannesmann Sachs Ag | Parallelhybridantrieb für ein Kraftfahrzeug mit in die elektrische Maschine integrierter Kupplung und zugehörige Elektromotorbaueinheit |
DE10118271A1 (de) | 2001-04-12 | 2002-03-14 | Henkel Kgaa | Diazothiazol-Farbstoffe |
CN1197916C (zh) | 2002-03-20 | 2005-04-20 | 上海市染料研究所 | 一种橄榄绿色阳离子染料及其制备方法 |
FR2838338B1 (fr) * | 2002-04-11 | 2004-05-28 | Oreal | Kit pour la teinture des fibres keratiniques |
ATE536915T1 (de) * | 2006-02-18 | 2011-12-15 | Wella GmbH | Mittel zum färben von keratinhaltigen fasern |
-
2006
- 2006-02-18 AT AT06003343T patent/ATE536915T1/de active
- 2006-02-18 EP EP06003343A patent/EP1820536B1/en not_active Not-in-force
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- 2007-02-09 MX MX2008010403A patent/MX2008010403A/es active IP Right Grant
- 2007-02-09 CN CN200780005873XA patent/CN101384303B/zh not_active Expired - Fee Related
- 2007-02-09 JP JP2008551946A patent/JP5431735B2/ja active Active
- 2007-02-09 WO PCT/IB2007/050428 patent/WO2007093943A1/en active Application Filing
- 2007-02-16 US US11/707,371 patent/US7513917B2/en active Active
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- 2009-02-26 US US12/393,539 patent/US7658771B2/en active Active
Also Published As
Publication number | Publication date |
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US7658771B2 (en) | 2010-02-09 |
US20070199161A1 (en) | 2007-08-30 |
US7513917B2 (en) | 2009-04-07 |
JP2009531279A (ja) | 2009-09-03 |
US20090158532A1 (en) | 2009-06-25 |
EP1820536B1 (en) | 2011-12-14 |
MX2008010403A (es) | 2008-09-23 |
JP5431735B2 (ja) | 2014-03-05 |
WO2007093943A1 (en) | 2007-08-23 |
CN101384303B (zh) | 2012-07-04 |
EP1820536A1 (en) | 2007-08-22 |
ATE536915T1 (de) | 2011-12-15 |
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