JP2004502666A - 2−ヒドロキシ−5−アミノ−ビフェニル−誘導体ならびにこの化合物を含有する酸化毛髪染色剤 - Google Patents
2−ヒドロキシ−5−アミノ−ビフェニル−誘導体ならびにこの化合物を含有する酸化毛髪染色剤 Download PDFInfo
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- JP2004502666A JP2004502666A JP2002507764A JP2002507764A JP2004502666A JP 2004502666 A JP2004502666 A JP 2004502666A JP 2002507764 A JP2002507764 A JP 2002507764A JP 2002507764 A JP2002507764 A JP 2002507764A JP 2004502666 A JP2004502666 A JP 2004502666A
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- Prior art keywords
- group
- amino
- hydroxy
- biphenyl
- hydrogen
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 11
- 239000000118 hair dye Substances 0.000 title description 7
- 239000000126 substance Substances 0.000 claims abstract description 35
- 210000004209 hair Anatomy 0.000 claims abstract description 25
- 238000004043 dyeing Methods 0.000 claims abstract description 24
- 239000003814 drug Substances 0.000 claims abstract description 12
- 229940079593 drug Drugs 0.000 claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 6
- 102000011782 Keratins Human genes 0.000 claims abstract description 5
- 108010076876 Keratins Proteins 0.000 claims abstract description 5
- 239000000835 fiber Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 32
- 150000002431 hydrogen Chemical group 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000003277 amino group Chemical group 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 239000004305 biphenyl Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- OUIITAOCYATDMY-UHFFFAOYSA-N 4-amino-2-phenylphenol Chemical group NC1=CC=C(O)C(C=2C=CC=CC=2)=C1 OUIITAOCYATDMY-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical group FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000000217 alkyl 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
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 4
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- LKGFIUAOMYSEJF-UHFFFAOYSA-N 4-amino-2-(4-aminophenyl)phenol Chemical group C1=CC(N)=CC=C1C1=CC(N)=CC=C1O LKGFIUAOMYSEJF-UHFFFAOYSA-N 0.000 claims description 3
- BZTCYXKUXFHCKD-UHFFFAOYSA-N 4-amino-2-(4-hydroxyphenyl)phenol Chemical group NC1=CC=C(O)C(C=2C=CC(O)=CC=2)=C1 BZTCYXKUXFHCKD-UHFFFAOYSA-N 0.000 claims description 3
- KQKIWZGNBJLCOS-UHFFFAOYSA-N 4-amino-2-(4-hydroxy-2-methylphenyl)phenol Chemical group CC1=CC(O)=CC=C1C1=CC(N)=CC=C1O KQKIWZGNBJLCOS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
- 238000010586 diagram Methods 0.000 abstract 1
- 238000001819 mass spectrum Methods 0.000 description 41
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical class BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 33
- -1 hydroxy, nitro, amino Chemical group 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000000975 dye Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000007800 oxidant agent Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 235000010323 ascorbic acid Nutrition 0.000 description 4
- 229960005070 ascorbic acid Drugs 0.000 description 4
- 239000011668 ascorbic acid Substances 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XWOXROPAWASYJZ-UHFFFAOYSA-N 2-bromo-1-(methoxymethoxy)-4-nitrobenzene Chemical compound COCOC1=CC=C([N+]([O-])=O)C=C1Br XWOXROPAWASYJZ-UHFFFAOYSA-N 0.000 description 3
- FIBBSIRCVZWBML-UHFFFAOYSA-N 4-nitro-2-phenylphenol Chemical group OC1=CC=C([N+]([O-])=O)C=C1C1=CC=CC=C1 FIBBSIRCVZWBML-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 235000015165 citric acid Nutrition 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000982 direct dye Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000037308 hair color Effects 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002453 shampoo Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-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
- LEUSKIRWDOWIQP-UHFFFAOYSA-N 2-(5-amino-2-hydroxyphenyl)benzonitrile Chemical group NC1=CC=C(O)C(C=2C(=CC=CC=2)C#N)=C1 LEUSKIRWDOWIQP-UHFFFAOYSA-N 0.000 description 2
- ZAKRQVGRLXCQOS-UHFFFAOYSA-N 3-(5-amino-2-hydroxyphenyl)benzonitrile Chemical group NC1=CC=C(O)C(C=2C=C(C=CC=2)C#N)=C1 ZAKRQVGRLXCQOS-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- 229940018563 3-aminophenol Drugs 0.000 description 2
- YAIDJNQGOBIQEF-UHFFFAOYSA-N 4-amino-2-(2-chlorophenyl)phenol Chemical group NC1=CC=C(O)C(C=2C(=CC=CC=2)Cl)=C1 YAIDJNQGOBIQEF-UHFFFAOYSA-N 0.000 description 2
- BDNYHCLBPVARRO-UHFFFAOYSA-N 4-amino-2-(2-fluorophenyl)phenol Chemical group NC1=CC=C(O)C(C=2C(=CC=CC=2)F)=C1 BDNYHCLBPVARRO-UHFFFAOYSA-N 0.000 description 2
- DVYSQOKCDAFDOF-UHFFFAOYSA-N 4-amino-2-(2-hydroxyphenyl)phenol Chemical group NC1=CC=C(O)C(C=2C(=CC=CC=2)O)=C1 DVYSQOKCDAFDOF-UHFFFAOYSA-N 0.000 description 2
- FERYBNHVGYTXLA-UHFFFAOYSA-N 4-amino-2-(2-methoxyphenyl)phenol Chemical group COC1=CC=CC=C1C1=CC(N)=CC=C1O FERYBNHVGYTXLA-UHFFFAOYSA-N 0.000 description 2
- ZRTVBMOXTNYVMJ-UHFFFAOYSA-N 4-amino-2-(2-methylphenyl)phenol Chemical group CC1=CC=CC=C1C1=CC(N)=CC=C1O ZRTVBMOXTNYVMJ-UHFFFAOYSA-N 0.000 description 2
- RPYYLLIZCYGYQM-UHFFFAOYSA-N 4-amino-2-(2-nitrophenyl)phenol Chemical group NC1=CC=C(O)C(C=2C(=CC=CC=2)[N+]([O-])=O)=C1 RPYYLLIZCYGYQM-UHFFFAOYSA-N 0.000 description 2
- FXJDOKHAQQNYEF-UHFFFAOYSA-N 4-amino-2-(3-aminophenyl)phenol Chemical group NC1=CC=CC(C=2C(=CC=C(N)C=2)O)=C1 FXJDOKHAQQNYEF-UHFFFAOYSA-N 0.000 description 2
- LWKDURXMFZMLNI-UHFFFAOYSA-N 4-amino-2-(3-chlorophenyl)phenol Chemical group NC1=CC=C(O)C(C=2C=C(Cl)C=CC=2)=C1 LWKDURXMFZMLNI-UHFFFAOYSA-N 0.000 description 2
- DDGKNFZSHDGESN-UHFFFAOYSA-N 4-amino-2-(3-fluorophenyl)phenol Chemical group NC1=CC=C(O)C(C=2C=C(F)C=CC=2)=C1 DDGKNFZSHDGESN-UHFFFAOYSA-N 0.000 description 2
- IKQOEYMZKVSOGX-UHFFFAOYSA-N 4-amino-2-(3-hydroxyphenyl)phenol Chemical group NC1=CC=C(O)C(C=2C=C(O)C=CC=2)=C1 IKQOEYMZKVSOGX-UHFFFAOYSA-N 0.000 description 2
- SRQLBVISKTWNNX-UHFFFAOYSA-N 4-amino-2-(3-methoxyphenyl)phenol Chemical group COC1=CC=CC(C=2C(=CC=C(N)C=2)O)=C1 SRQLBVISKTWNNX-UHFFFAOYSA-N 0.000 description 2
- SPLIFXAPPAZYAG-UHFFFAOYSA-N 4-amino-2-(3-methylphenyl)phenol Chemical group CC1=CC=CC(C=2C(=CC=C(N)C=2)O)=C1 SPLIFXAPPAZYAG-UHFFFAOYSA-N 0.000 description 2
- XSGJVFPBTXJYER-UHFFFAOYSA-N 4-amino-2-(3-methylsulfanylphenyl)phenol Chemical group CSC1=CC=CC(C=2C(=CC=C(N)C=2)O)=C1 XSGJVFPBTXJYER-UHFFFAOYSA-N 0.000 description 2
- KDKJCTDUUJQJTC-UHFFFAOYSA-N 4-amino-2-(3-nitrophenyl)phenol Chemical group NC1=CC=C(O)C(C=2C=C(C=CC=2)[N+]([O-])=O)=C1 KDKJCTDUUJQJTC-UHFFFAOYSA-N 0.000 description 2
- RMHQKTAMFXQMQJ-UHFFFAOYSA-N 4-amino-2-[2-(aminomethyl)phenyl]phenol Chemical group NCC1=CC=CC=C1C1=CC(N)=CC=C1O RMHQKTAMFXQMQJ-UHFFFAOYSA-N 0.000 description 2
- AUOLBVLKSOGDTH-UHFFFAOYSA-N 4-amino-2-[3-(aminomethyl)phenyl]phenol Chemical group NCC1=CC=CC(C=2C(=CC=C(N)C=2)O)=C1 AUOLBVLKSOGDTH-UHFFFAOYSA-N 0.000 description 2
- SGNZYJXNUURYCH-UHFFFAOYSA-N 5,6-dihydroxyindole Chemical compound C1=C(O)C(O)=CC2=C1NC=C2 SGNZYJXNUURYCH-UHFFFAOYSA-N 0.000 description 2
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 101150003085 Pdcl gene Proteins 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Chemical compound OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 229940096992 potassium oleate Drugs 0.000 description 2
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
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- 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
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- 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
- A61K8/415—Aminophenols
-
- 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
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
- C07C215/78—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring containing at least two hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
- C07C215/80—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring containing at least two amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
- C07C255/59—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10032134A DE10032134C1 (de) | 2000-07-01 | 2000-07-01 | 2-Hydroxy-5-amino-biphenyl-Derivate sowie diese Verbindungen enthaltende Oxidationshaarfärbemittel |
| PCT/EP2001/002704 WO2002002507A1 (de) | 2000-07-01 | 2001-03-10 | 2-hydroxy-5-amino-biphenyl-derivate sowie diese verbindungen enthaltende oxidationshaarfärbemittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004502666A true JP2004502666A (ja) | 2004-01-29 |
| JP2004502666A5 JP2004502666A5 (enExample) | 2004-12-24 |
Family
ID=7647508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002507764A Withdrawn JP2004502666A (ja) | 2000-07-01 | 2001-03-10 | 2−ヒドロキシ−5−アミノ−ビフェニル−誘導体ならびにこの化合物を含有する酸化毛髪染色剤 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6749644B2 (enExample) |
| EP (1) | EP1208077B1 (enExample) |
| JP (1) | JP2004502666A (enExample) |
| AT (1) | ATE264832T1 (enExample) |
| AU (1) | AU2001262088A1 (enExample) |
| BR (1) | BR0106932A (enExample) |
| CA (1) | CA2383577A1 (enExample) |
| DE (2) | DE10032134C1 (enExample) |
| ES (1) | ES2219525T3 (enExample) |
| MX (1) | MXPA02002199A (enExample) |
| WO (1) | WO2002002507A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10048733A1 (de) * | 2000-09-29 | 2002-04-18 | Henkel Kgaa | Oxidationsfärbemittel mit 2-Amino-5-methylphenol |
| DE10141722A1 (de) * | 2001-08-25 | 2003-03-06 | Wella Ag | 3-Aminophenol-Derivate enthaltende Oxidationshaarfärbemittel sowie neue 3-Aminophenol-Derivate |
| DE10217270A1 (de) | 2002-04-18 | 2003-11-06 | Wella Ag | In 2-Stellung substituierte 3-Aminophenol-Derivate sowie diese Verbindungen enthaltende Färbemittel |
| DE102004002604A1 (de) * | 2004-01-15 | 2005-08-04 | Beiersdorf Ag | Visualisierung von Sonnenschutzmitteln auf der Haut |
| US8110015B2 (en) | 2007-05-30 | 2012-02-07 | Illinois Tool Works, Inc. | Method and apparatus for removing contaminants from a reflow apparatus |
| DE102008049675A1 (de) | 2008-09-30 | 2010-04-01 | Markus Dr. Heinrich | Verfahren zur Herstellung von 3-Aminobiphenylen |
| EP2226065A3 (en) * | 2010-03-15 | 2010-09-29 | KPSS-Kao Professional Salon Services GmbH | Colouring composition for keratin fibres |
| CN102344411B (zh) * | 2011-08-01 | 2013-05-15 | 宜兴市新宇化工有限公司 | 一种制备2,6-二甲氧基-3,5-二氨基吡啶盐酸盐的方法 |
| CN103239364A (zh) * | 2013-05-31 | 2013-08-14 | 江南大学 | 用于浅色调染发剂的偶合剂 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5033891B2 (enExample) * | 1971-10-29 | 1975-11-04 | ||
| DE2518393A1 (de) * | 1975-04-25 | 1976-11-04 | Henkel & Cie Gmbh | Haarfaerbemittel |
| DE2659056A1 (de) * | 1976-12-27 | 1978-07-06 | Henkel Kgaa | Haarfaerbemittel |
| ATE4422T1 (de) * | 1979-10-18 | 1983-08-15 | Warner-Lambert Company | Substituierte 5-((7-chlor-4-chinolinyl)amino)-3(aminomethyl)-(1,1'-biphenyl)-2-ol-verbindungen verfahren zu ihrer herstellung; und die verbindungen enthaltende pharmazeutische zusammensetzungen. |
| DE19717222A1 (de) * | 1997-04-24 | 1998-10-29 | Henkel Kgaa | Mittel zum Färben von keratinhaltigen Fasern |
| DE19822041A1 (de) * | 1998-05-16 | 1999-12-23 | Wella Ag | 2,5-Diamino-1-phenylbenzol-Derivate enthaltende Oxidationshaarfärbemittel sowie neue 2,5-Diamino-1-phenylbenzol-Derivate |
-
2000
- 2000-07-01 DE DE10032134A patent/DE10032134C1/de not_active Expired - Fee Related
-
2001
- 2001-03-10 AU AU2001262088A patent/AU2001262088A1/en not_active Abandoned
- 2001-03-10 BR BR0106932-2A patent/BR0106932A/pt not_active Application Discontinuation
- 2001-03-10 US US10/049,346 patent/US6749644B2/en not_active Expired - Lifetime
- 2001-03-10 MX MXPA02002199A patent/MXPA02002199A/es active IP Right Grant
- 2001-03-10 CA CA002383577A patent/CA2383577A1/en not_active Abandoned
- 2001-03-10 WO PCT/EP2001/002704 patent/WO2002002507A1/de not_active Ceased
- 2001-03-10 EP EP01936066A patent/EP1208077B1/de not_active Expired - Lifetime
- 2001-03-10 AT AT01936066T patent/ATE264832T1/de not_active IP Right Cessation
- 2001-03-10 DE DE50102041T patent/DE50102041D1/de not_active Expired - Lifetime
- 2001-03-10 ES ES01936066T patent/ES2219525T3/es not_active Expired - Lifetime
- 2001-03-10 JP JP2002507764A patent/JP2004502666A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE50102041D1 (de) | 2004-05-27 |
| ATE264832T1 (de) | 2004-05-15 |
| EP1208077B1 (de) | 2004-04-21 |
| ES2219525T3 (es) | 2004-12-01 |
| CA2383577A1 (en) | 2002-01-10 |
| AU2001262088A1 (en) | 2002-01-14 |
| BR0106932A (pt) | 2002-05-14 |
| MXPA02002199A (es) | 2002-09-30 |
| DE10032134C1 (de) | 2001-12-13 |
| US20020166180A1 (en) | 2002-11-14 |
| US6749644B2 (en) | 2004-06-15 |
| EP1208077A1 (de) | 2002-05-29 |
| WO2002002507A1 (de) | 2002-01-10 |
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