EP1562539A1 - 4-amino-biphenyl-3-ol-derivate enthaltende mittel zum färben von keratinfasern - Google Patents
4-amino-biphenyl-3-ol-derivate enthaltende mittel zum färben von keratinfasernInfo
- Publication number
- EP1562539A1 EP1562539A1 EP03725188A EP03725188A EP1562539A1 EP 1562539 A1 EP1562539 A1 EP 1562539A1 EP 03725188 A EP03725188 A EP 03725188A EP 03725188 A EP03725188 A EP 03725188A EP 1562539 A1 EP1562539 A1 EP 1562539A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- amino
- biphenyl
- chloro
- methyl
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 10
- 102000011782 Keratins Human genes 0.000 title claims abstract description 8
- 108010076876 Keratins Proteins 0.000 title claims abstract description 8
- 239000000835 fiber Substances 0.000 title claims abstract description 8
- 238000004043 dyeing Methods 0.000 title abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical group FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract 2
- ILGJVPVZCNNBKI-UHFFFAOYSA-N 2-amino-5-phenylphenol Chemical class C1=C(O)C(N)=CC=C1C1=CC=CC=C1 ILGJVPVZCNNBKI-UHFFFAOYSA-N 0.000 claims description 27
- 239000000126 substance Substances 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- 239000000975 dye Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 11
- GHWFZNQKPILXGQ-UHFFFAOYSA-N 2-amino-5-(2-chlorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=CC=C1Cl GHWFZNQKPILXGQ-UHFFFAOYSA-N 0.000 claims description 9
- -1 4-amino-2 ' Chemical compound 0.000 claims description 9
- 238000004040 coloring Methods 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 7
- GKVAFMXXVWUZSB-UHFFFAOYSA-N 2-amino-5-(2-fluorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=CC=C1F GKVAFMXXVWUZSB-UHFFFAOYSA-N 0.000 claims description 6
- RRJKVOQVXQLAQR-UHFFFAOYSA-N 2-amino-5-(3-chlorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=CC(Cl)=C1 RRJKVOQVXQLAQR-UHFFFAOYSA-N 0.000 claims description 6
- LABQYTDHTJDQOH-UHFFFAOYSA-N 2-amino-5-(4-fluorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=C(F)C=C1 LABQYTDHTJDQOH-UHFFFAOYSA-N 0.000 claims description 6
- LQXKXHZDYRVUHE-UHFFFAOYSA-N 2-amino-5-(3-fluorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=CC(F)=C1 LQXKXHZDYRVUHE-UHFFFAOYSA-N 0.000 claims description 5
- YQKOXMJCZSOAET-UHFFFAOYSA-N 2-amino-5-(4-chlorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=C(Cl)C=C1 YQKOXMJCZSOAET-UHFFFAOYSA-N 0.000 claims description 5
- UBUPBIVXLRGKHR-UHFFFAOYSA-N 2-amino-5-(2-chloro-6-fluorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=C(F)C=CC=C1Cl UBUPBIVXLRGKHR-UHFFFAOYSA-N 0.000 claims description 4
- YFQOTRXGRZRVEE-UHFFFAOYSA-N 2-amino-5-(3-chloro-5-fluorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC(F)=CC(Cl)=C1 YFQOTRXGRZRVEE-UHFFFAOYSA-N 0.000 claims description 4
- DEKCJFVPAKHVFE-UHFFFAOYSA-N 2-amino-5-(4-methylphenyl)phenol Chemical compound C1=CC(C)=CC=C1C1=CC=C(N)C(O)=C1 DEKCJFVPAKHVFE-UHFFFAOYSA-N 0.000 claims description 4
- 239000000982 direct dye Substances 0.000 claims description 4
- TVOKNGHLKITSMJ-UHFFFAOYSA-N 2-amino-5-(2-chloro-6-methylphenyl)phenol Chemical compound CC1=CC=CC(Cl)=C1C1=CC=C(N)C(O)=C1 TVOKNGHLKITSMJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- OYADOPYVPUFPLJ-UHFFFAOYSA-N 2-(4-amino-3-hydroxyphenyl)benzonitrile Chemical compound C1=C(O)C(N)=CC=C1C1=CC=CC=C1C#N OYADOPYVPUFPLJ-UHFFFAOYSA-N 0.000 claims description 2
- JYBXDZIEHAOWTA-UHFFFAOYSA-N 2-amino-5-(2,3-dichlorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=CC(Cl)=C1Cl JYBXDZIEHAOWTA-UHFFFAOYSA-N 0.000 claims description 2
- XLNOFHJMNRQUSM-UHFFFAOYSA-N 2-amino-5-(2,4-difluorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=C(F)C=C1F XLNOFHJMNRQUSM-UHFFFAOYSA-N 0.000 claims description 2
- KOABFHRCJCLLIL-UHFFFAOYSA-N 2-amino-5-(2,4-dimethylphenyl)phenol Chemical compound CC1=CC(C)=CC=C1C1=CC=C(N)C(O)=C1 KOABFHRCJCLLIL-UHFFFAOYSA-N 0.000 claims description 2
- FCLLVNMBEUAYQL-UHFFFAOYSA-N 2-amino-5-(2,5-dichlorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC(Cl)=CC=C1Cl FCLLVNMBEUAYQL-UHFFFAOYSA-N 0.000 claims description 2
- KPWYIQLCMYVKKS-UHFFFAOYSA-N 2-amino-5-(2,6-dichlorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=C(Cl)C=CC=C1Cl KPWYIQLCMYVKKS-UHFFFAOYSA-N 0.000 claims description 2
- KBRHXLVGTJYXQU-UHFFFAOYSA-N 2-amino-5-(2-chloro-3-fluorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=CC(F)=C1Cl KBRHXLVGTJYXQU-UHFFFAOYSA-N 0.000 claims description 2
- CFSYJDLSIGQZFI-UHFFFAOYSA-N 2-amino-5-(2-chloro-5-fluorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC(F)=CC=C1Cl CFSYJDLSIGQZFI-UHFFFAOYSA-N 0.000 claims description 2
- QAIUKXHVEUHXJB-UHFFFAOYSA-N 2-amino-5-(2-fluoro-4-methylphenyl)phenol Chemical compound FC1=CC(C)=CC=C1C1=CC=C(N)C(O)=C1 QAIUKXHVEUHXJB-UHFFFAOYSA-N 0.000 claims description 2
- MINHKBKSTMTJFN-UHFFFAOYSA-N 2-amino-5-(2-methylphenyl)phenol Chemical compound CC1=CC=CC=C1C1=CC=C(N)C(O)=C1 MINHKBKSTMTJFN-UHFFFAOYSA-N 0.000 claims description 2
- YSTXGAYUBFRHNP-UHFFFAOYSA-N 2-amino-5-(3,4-difluorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=C(F)C(F)=C1 YSTXGAYUBFRHNP-UHFFFAOYSA-N 0.000 claims description 2
- NNDGITWCECFDCE-UHFFFAOYSA-N 2-amino-5-(3,4-dimethylphenyl)phenol Chemical compound C1=C(C)C(C)=CC=C1C1=CC=C(N)C(O)=C1 NNDGITWCECFDCE-UHFFFAOYSA-N 0.000 claims description 2
- OTNCGQSUIZQSOS-UHFFFAOYSA-N 2-amino-5-(3-chloro-2-fluorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=CC(Cl)=C1F OTNCGQSUIZQSOS-UHFFFAOYSA-N 0.000 claims description 2
- FVIUZELCLYVPJQ-UHFFFAOYSA-N 2-amino-5-(3-fluoro-2-methylphenyl)phenol Chemical compound CC1=C(F)C=CC=C1C1=CC=C(N)C(O)=C1 FVIUZELCLYVPJQ-UHFFFAOYSA-N 0.000 claims description 2
- ONTDCULXBJMRCV-UHFFFAOYSA-N 2-amino-5-(3-methylphenyl)phenol Chemical compound CC1=CC=CC(C=2C=C(O)C(N)=CC=2)=C1 ONTDCULXBJMRCV-UHFFFAOYSA-N 0.000 claims description 2
- RKKMFZFSMJFLDQ-UHFFFAOYSA-N 2-amino-5-(5-chloro-2-methylphenyl)phenol Chemical compound CC1=CC=C(Cl)C=C1C1=CC=C(N)C(O)=C1 RKKMFZFSMJFLDQ-UHFFFAOYSA-N 0.000 claims description 2
- GJZGPWSUNSLAGK-UHFFFAOYSA-N 2-amino-5-(5-fluoro-2-methylphenyl)phenol Chemical compound CC1=CC=C(F)C=C1C1=CC=C(N)C(O)=C1 GJZGPWSUNSLAGK-UHFFFAOYSA-N 0.000 claims description 2
- YINYOLZRVSSLNW-UHFFFAOYSA-N 2-amino-5-[2-(trifluoromethyl)phenyl]phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=CC=C1C(F)(F)F YINYOLZRVSSLNW-UHFFFAOYSA-N 0.000 claims description 2
- KHUGNORXKTUXEV-UHFFFAOYSA-N 2-amino-5-[3-(trifluoromethyl)phenyl]phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=CC(C(F)(F)F)=C1 KHUGNORXKTUXEV-UHFFFAOYSA-N 0.000 claims description 2
- KREQJTXMMZPJKZ-UHFFFAOYSA-N 2-amino-5-[4-(trifluoromethyl)phenyl]phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=C(C(F)(F)F)C=C1 KREQJTXMMZPJKZ-UHFFFAOYSA-N 0.000 claims description 2
- XABKCKBNYAFHGB-UHFFFAOYSA-N 3-(3-methylphenyl)phenol Chemical compound CC1=CC=CC(C=2C=C(O)C=CC=2)=C1 XABKCKBNYAFHGB-UHFFFAOYSA-N 0.000 claims description 2
- ZTKAAMGKAAZJDD-UHFFFAOYSA-N 3-(4-amino-3-hydroxyphenyl)benzonitrile Chemical compound C1=C(O)C(N)=CC=C1C1=CC=CC(C#N)=C1 ZTKAAMGKAAZJDD-UHFFFAOYSA-N 0.000 claims description 2
- RIAXZPFBTMUMKT-UHFFFAOYSA-N 4-(4-amino-3-hydroxyphenyl)benzonitrile Chemical compound C1=C(O)C(N)=CC=C1C1=CC=C(C#N)C=C1 RIAXZPFBTMUMKT-UHFFFAOYSA-N 0.000 claims description 2
- HDBRQLBYYZBDKC-UHFFFAOYSA-N 2-amino-5-(3-fluoro-5-methylphenyl)phenol Chemical compound CC1=CC(F)=CC(C=2C=C(O)C(N)=CC=2)=C1 HDBRQLBYYZBDKC-UHFFFAOYSA-N 0.000 claims 2
- SEOXJFIYKSRNBD-UHFFFAOYSA-N 2-amino-5-(2,3-difluorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=CC(F)=C1F SEOXJFIYKSRNBD-UHFFFAOYSA-N 0.000 claims 1
- LPRXUDIITAOGAN-UHFFFAOYSA-N 2-amino-5-(2,5-dimethylphenyl)phenol Chemical compound CC1=CC=C(C)C(C=2C=C(O)C(N)=CC=2)=C1 LPRXUDIITAOGAN-UHFFFAOYSA-N 0.000 claims 1
- IUHTXBAIKZSMKF-UHFFFAOYSA-N 2-amino-5-(2-chloro-3-methylphenyl)phenol Chemical compound CC1=CC=CC(C=2C=C(O)C(N)=CC=2)=C1Cl IUHTXBAIKZSMKF-UHFFFAOYSA-N 0.000 claims 1
- CFKJDVNTZYKHPO-UHFFFAOYSA-N 2-amino-5-(2-chloro-4-fluorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=C(F)C=C1Cl CFKJDVNTZYKHPO-UHFFFAOYSA-N 0.000 claims 1
- PFHVKQBCUOWAJK-UHFFFAOYSA-N 2-amino-5-(2-fluoro-6-methylphenyl)phenol Chemical compound CC1=CC=CC(F)=C1C1=CC=C(N)C(O)=C1 PFHVKQBCUOWAJK-UHFFFAOYSA-N 0.000 claims 1
- PZBNVKVNIBBOPI-UHFFFAOYSA-N 2-amino-5-(3,5-dichlorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC(Cl)=CC(Cl)=C1 PZBNVKVNIBBOPI-UHFFFAOYSA-N 0.000 claims 1
- ZTBVILLRRKWHNH-UHFFFAOYSA-N 2-amino-5-(3,5-difluorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC(F)=CC(F)=C1 ZTBVILLRRKWHNH-UHFFFAOYSA-N 0.000 claims 1
- SNJFLLQMJLSLTM-UHFFFAOYSA-N 2-amino-5-(3-chloro-4-fluorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=C(F)C(Cl)=C1 SNJFLLQMJLSLTM-UHFFFAOYSA-N 0.000 claims 1
- QDMHJTHXTOACNJ-UHFFFAOYSA-N 2-amino-5-(3-fluoro-4-methylphenyl)phenol Chemical compound C1=C(F)C(C)=CC=C1C1=CC=C(N)C(O)=C1 QDMHJTHXTOACNJ-UHFFFAOYSA-N 0.000 claims 1
- KHXCTAWYXVOGSZ-UHFFFAOYSA-N 2-amino-5-(4-chloro-2-fluorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=C(Cl)C=C1F KHXCTAWYXVOGSZ-UHFFFAOYSA-N 0.000 claims 1
- QZPCPKUZBSNUHW-UHFFFAOYSA-N 2-amino-5-(4-chloro-2-methylphenyl)phenol Chemical compound CC1=CC(Cl)=CC=C1C1=CC=C(N)C(O)=C1 QZPCPKUZBSNUHW-UHFFFAOYSA-N 0.000 claims 1
- WLRCVCCHMSWJLU-UHFFFAOYSA-N 2-amino-5-(4-chloro-3-methylphenyl)phenol Chemical compound C1=C(Cl)C(C)=CC(C=2C=C(O)C(N)=CC=2)=C1 WLRCVCCHMSWJLU-UHFFFAOYSA-N 0.000 claims 1
- OAERRCRIAPZUKA-UHFFFAOYSA-N 2-amino-5-(4-fluoro-2-methylphenyl)phenol Chemical compound CC1=CC(F)=CC=C1C1=CC=C(N)C(O)=C1 OAERRCRIAPZUKA-UHFFFAOYSA-N 0.000 claims 1
- OCNFTSBQEYJSKA-UHFFFAOYSA-N 2-amino-5-(5-chloro-2-fluorophenyl)phenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC(Cl)=CC=C1F OCNFTSBQEYJSKA-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 229910007161 Si(CH3)3 Inorganic materials 0.000 abstract 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 239000000118 hair dye Substances 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003086 colorant Substances 0.000 description 9
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
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- 230000015572 biosynthetic process Effects 0.000 description 7
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000007800 oxidant agent Substances 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000002904 solvent 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
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- 230000002378 acidificating effect Effects 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
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- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
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- 229930195729 fatty acid Natural products 0.000 description 3
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- 150000007524 organic acids Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
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- 238000002360 preparation method Methods 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 239000000080 wetting agent Substances 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
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- HCPJEHJGFKWRFM-UHFFFAOYSA-N 2-amino-5-methylphenol Chemical compound CC1=CC=C(N)C(O)=C1 HCPJEHJGFKWRFM-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
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- 239000000978 natural dye Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 1
- 238000010979 pH adjustment 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
- 239000002304 perfume Substances 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- QXYMVUZOGFVPGH-UHFFFAOYSA-N picramic acid Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O QXYMVUZOGFVPGH-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229940001482 sodium sulfite Drugs 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- GUQPDKHHVFLXHS-UHFFFAOYSA-M sodium;2-(2-dodecoxyethoxy)ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOS([O-])(=O)=O GUQPDKHHVFLXHS-UHFFFAOYSA-M 0.000 description 1
- 239000008107 starch Chemical class 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 239000001003 triarylmethane dye Substances 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
- 238000005406 washing Methods 0.000 description 1
- 239000001043 yellow dye 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
- A61K8/69—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine
-
- 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
Definitions
- the present invention relates to agents for the oxidative dyeing of keratin fibers, in particular human hair, containing 4-amino-biphenyl-3-ol derivatives.
- Oxidation dyes have become very important in the field of coloring keratin fibers, in particular hair coloring.
- the coloration arises from the reaction of certain developer substances with certain coupler substances in the presence of a suitable oxidizing agent.
- 2,5-diaminotoluene, 2,5-diaminophenylethyl alcohol, p-aminophenol, 1,4-diaminobenzene and 4,5-diamino-1- (2-hydroxyethyl) pyrazole are used as developer substances, while resorcinol, 2 -Methyl-resorcinol, 1-naphthol, 3-aminophenol, m-phenylene-diamine, 2-amino-4- (2'-hydroxyethyl) amino-anisole, 1, 3-diamino-4- (2'-hydroxyethoxy) benzene and 2,4-diamino-5-fluorotoluene are mentioned.
- oxidation dyes which are used to dye human hair.
- the dyes have to be harmless from a toxicological and dermatological point of view, and the hair colorations achieved should have good light fastness, perm, fastness to rubbing and stability to shampooing and sufficient resistance to Have perspiration. It is also necessary that a wide range of different color shades can be produced by combining suitable developer substances and coupler substances.
- DE-OS 28 33 989 proposes the use of 6-amino-3-methylphenol as an oxidative yellow dye in oxidative hair dyes to solve the problem described.
- This compound is said to have good suitability as a shading dye for producing light blonde tones and gold tones, although the requirements made, in particular with regard to the resistance of the hair colors to the action of permanent waving agents, are not fully met.
- the present invention therefore relates to an agent for the oxidative dyeing of keratin fibers, which is characterized in that it contains at least one 4-aminobiphenyl-3-ol derivative of the general formula (I) or its physiologically tolerable, water-soluble salts,
- R1 and R2 independently of one another are hydrogen, a halogen atom, a cyano group, a hydroxy group, a C 1 -C 4 alkoxy group, a C 2 -C 4 hydroxyalkoxy group, a C, -C 6 alkyl group, a nitro group, a trifluoromethane group , one -C (0) H group, a -C (O) CH 3 group, a -C (0) CF 3 group, a -Si (CH 3 ) 3 group or a C, -C 6 hydroxyalkyl - mean group, or R1 and R2 together form an -O-CH2-O- bridge.
- Preferred compounds of the formula (I) are those in which (i) R1 is hydrogen and / or (ii) R2 is hydrogen, a methyl group, a trifluoromethyl group, a fluorine atom or a chlorine atom.
- the following compounds of the formula (I) are particularly preferred: 4-amino-biphenyl-3-ol, 4-amino-2'-chlorobiphenyl-3-ol, 4-amino-3'-chlorobiphenyl-3- ol, 4-amino-4'-chlorobiphenyl-3-ol, 4-amino-2'-fluoro-biphenyl-3-ol, 4-amino-3 , -fluorobiphenyl-3-ol, 4-amino -4'-fluoro-biphenyl-3-ol and their physiologically tolerable salts.
- the 4-aminobiphenyl-3-ol derivatives of the formula (I) according to the invention can be prepared using known synthetic processes; for example by a palladium (O) catalyzed coupling of a substituted benzene of the formula (II)
- Rb represents a halogen atom and Rd represents B (OH) 2
- Rb represents B (OH) 2 and Rd represents a halogen atom
- R1 and R2 has the meaning given in the formula (I); with subsequent reduction and splitting off of the protective group.
- the compounds of formula (I) according to the invention enable dyeings with excellent color fastness, in particular with regard to wash fastness and rub fastness as well as permanent wave fastness.
- the 4-aminobiphenyl-3-ol derivative of the formula (I) is present in the colorant according to the invention in an amount of about 0.001 to 5 percent by weight, an amount of about 0.005 to 2 percent by weight and in particular 0.01 to 1 percent by weight is preferred.
- the compounds of formula (I) dye keratin fibers, especially human hair, without the addition of further dyes in yellow
- one or more conventional pxidative dyes for example developer substances or Coupler substances, alone or in a mixture with one another, are added.
- Coupling substances used here are, in particular, N- (3-dimethylamino-phenyl) urea, 2,6-diamino-pyridine, 2-amino-4 - [(2-hydroxyethyl) amino] anisole, 2,4- Diamino-1-fluoro-5-methyl-benzene, 2,4-diamino-1-methoxy-5-methyl-benzene, 2,4-diamino-1-ethoxy-5-methyl-benzene, 2,4-diamino 1- (2-hydroxyethoxy) -5-methyl-benzene, 2,4-di [(2-hydroxyethyl) amino] -1, 5-dimethoxy-benzene, 2,3-diamino-6-methoxy-pyridine, 3-amino-6-methoxy-2- (methylamino) pyridine, 2,6-diamino-3,5-dimethoxy-pyridine, 3,5-diamino-2,6-dimethoxy-pyridine
- 1,4-Diamino-benzene (p-phenylenediamine), 1,4-diamino-2-methyl-benzene (p-toluenediamine), 1,4-diamino-2,6-dimethyl-benzene, 1,4 4-diamino-3,5-diethyl-benzene, 1,4-diamino-2,5-dimethyl-benzene, 1,4-diamino-2,3-dimethyl-benzene, 2-chloro-1,4-diaminobenzene, 1,4-diamino-2- (thiophene-2-yl) benzene, 1,4-diamino-2- (thiophene-3-yl) benzene, 4- (2,5-diaminophenyl) -2 - ((diethyl- amino) methyl) thiophene, 2-chloro-3- (2,5-diaminophenyl) thiophene,
- the total amount of the aforementioned developer substances and coupler substances in the agent according to the invention is about 0.01 to 12 percent by weight, in particular about 0.2 to 6 percent by weight.
- the colorant according to the invention can also contain other color components, for example 4- (2,5-diamino-benzylamino) aniline or 3- (2,5-diamino-benzylamino) aniline, and also conventional natural, nature-identical or synthetic direct dyes from the Group of anionic (acidic) and cationic (basic) dyes, triarylmethane dyes, nitro dyes, disperse dyes and azo dyes, for example natural dyes such as indigo or henna, triphenylmethane dyes such as 4 - [(4'-amino-phenyl) - ( 4'imino-2 ", 5" -cyclohexadien-1 "-ylidene) -methyl] -2-methyl-aminobenzene-monohydrochloride (Cl 42 510) and 4 - [(4 , -amino-3'-methyl-phenyl) - (4 "-imino-3" -methyl)
- the aforementioned developer substances and / or coupler substances and / or other color components in combination with the compounds of the formula (I) according to the invention enable a large number of different color shades. For example, by using a combination of the compounds of formula (I) with 4- (2,5-diamino-benzylamino) aniline, it is possible to achieve blonde to brown hair colorations.
- the coupler substances and developer substances as well as the other color components can also be in the form of their physiologically compatible salts with organic or inorganic acids, such as hydrochloric acid or sulfuric acid, or - if they have aromatic OH groups - in the form of the salts
- organic or inorganic acids such as hydrochloric acid or sulfuric acid
- Bases for example as alkali phenolates, can be used.
- the colorants may also contain other customary cosmetic additives, for example antioxidants such as ascorbic acid, thioglycolic acid or sodium sulfite, and also perfume oils, complexing agents, wetting agents, emulsifiers, thickeners and care agents.
- antioxidants such as ascorbic acid, thioglycolic acid or sodium sulfite
- perfume oils such as ascorbic acid, thioglycolic acid or sodium sulfite
- complexing agents such ascorbic acid, thioglycolic acid or sodium sulfite
- wetting agents such ascorbic acid, thioglycolic acid or sodium sulfite
- perfume oils such ascorbic acid, thioglycolic acid or sodium sulfite
- complexing agents such ascorbic acid, thioglycolic acid or sodium sulfite
- wetting agents such ascorbic acid, thioglycolic acid or sodium sulfite
- the preparation form of the colorant according to the invention can, for example, be a solution, in particular an aqueous or aqueous-alcoholic solution, a paste, a cream, a gel, an emulsion or be an aerosol preparation.
- Their composition represents a mixture of the dye components with the additives customary for such preparations.
- Usual additives in solutions, creams, emulsions or gels are, for example, solvents such as water, lower aliphatic alcohols, for example ethanol, propanol or isopropanol, glycerol or glycols such as 1,2-propylene glycol, furthermore wetting agents or emulsifiers from the classes of the anionic, cationic, amphoteric or nonionic surfactants such as fatty alcohol sulfates, ethoxylated fatty alcohol sulfates, alkylsulfonates, alkylbenzenesulfonates, alkyltrimethylammonium salts, alkylbetaines, oxyethylated fatty alcohols, oxyethylated nonylphenols, fatty acid alkanolamides and oxyethylated fatty acid ester, also thickeners such as higher fatty alcohols, starch, cellulose derivatives, petrolatum, paraffin oil and fatty acids, and
- ingredients mentioned are used in the amounts customary for such purposes, for example the wetting agents and emulsifiers in concentrations of about 0.5 to 30 percent by weight, the thickeners in an amount of about 0.1 to 30 percent by weight and the care substances in a concentration of about 0.1 to 5 weight percent.
- the colorant according to the invention can react weakly acidic, neutral or alkaline.
- it has a pH of 6.5 to 11.5
- the basic adjustment preferably using ammonia or organic amines, for example monoethanolamine and triethanolamine, or else amino acids or inorganic bases such as sodium hydroxide and potassium hydroxide.
- ammonia or organic amines for example monoethanolamine and triethanolamine
- amino acids or inorganic bases such as sodium hydroxide and potassium hydroxide.
- Inorganic or organic acids for example phosphoric acid, acetic acid, citric acid or tartaric acid, are suitable for pH adjustment in the acidic range.
- the colorant described above is mixed with an oxidizing agent immediately before use, and an amount sufficient for the hair dyeing treatment, depending on the fullness of the hair, generally about 60 to 200 grams, of this mixture is applied to the hair.
- the main oxidizing agents used to develop hair color are hydrogen peroxide or its addition compounds with urea, melamine, sodium borate or sodium carbonate in the form of a 3 to 12 percent, preferably ⁇ percent, aqueous solution, but also atmospheric oxygen. If a ⁇ percent hydrogen peroxide solution is used as the oxidizing agent, the weight ratio between hair dye and oxidizing agent is 5: 1 to 1: 2, but preferably 1: 1. Larger amounts of oxidizing agent are used above all at higher dye concentrations in the hair dye or when more bleaching of the hair is intended at the same time.
- the mixture is allowed to act on the hair at 15 to 50 degrees Celsius for about 10 to 45 minutes, preferably 30 minutes, then the hair is rinsed with water and dried. If necessary, this rinse is washed with a shampoo and, if necessary, with a weak organic acid, such as Example citric acid or tartaric acid, rinsed. The hair is then dried.
- the hair colorants according to the invention with a content of 4-aminobiphenyl-3-ol derivatives of the formula (I) enable hair colorations with excellent color fastness, in particular with regard to light fastness, wash fastness and rub fastness as well as permanent wave fastness.
- the hair colorants according to the invention offer a wide range of different color shades, depending on the type and composition of the color components, which ranges from blonde to brown, purple, violet to blue and black shades. The shades are characterized by their special color intensity and a good color balance between damaged and undamaged hair.
- the very good coloring properties of the hair colorants according to the present application are further shown in the fact that these agents enable graying, chemically not previously damaged hair to be colored easily and with good coverage.
- the present invention further provides 4-aminobiphenyl-3-ol derivatives of the formula (I), the 4-aminobiphenyl-3-ol and 4-amino-2'-chlorobiphenyl-3- ol, the 4-amino-3'-chlorobiphenyl-3-ol, the 4-amino-4'-chlorobiphenyl-3-ol, the 4-amino-2'-fluorobiphenyl-3-ol, 4-amino-3'-fluoro-biphenyl-3-ol and 4-amino-4'-fluoro-biphenyl-3-ol and their physiologically tolerable salts are particularly preferred.
- reaction mixture is poured into 100 ml of ethyl acetate, the organic phase is extracted with dilute sodium hydroxide solution and then dried with magnesium sulfate.
- the Solvent is distilled off on a rotary evaporator and the
- the product thus obtained is heated to 50 ° C. in 50 ml of ethanol.
- reaction mixture is poured into 100 ml of ethyl acetate, the organic phase is extracted with dilute sodium hydroxide solution and then dried with magnesium sulfate. The solvent is distilled off on a rotary evaporator and the residue is purified on silica gel with hexane / ethyl acetate (9: 1).
- the product thus obtained is heated to 50 ° C. in 50 ml of ethanol. 80 ml of a 2.9 molar ethanolic hydrochloric acid solution are then added dropwise. The reaction mixture is cooled to 0 ° C. The precipitate is filtered off, washed twice with 20 ml of ethanol and then dried.
- Cream-shaped ink carrier compositions of the following composition are produced:
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10251106A DE10251106A1 (de) | 2002-11-02 | 2002-11-02 | 4-Amino-biphenyl-3-ol-Derivate enthaltende Mittel zum Färben von Keratinfasern |
| DE10251106 | 2002-11-02 | ||
| PCT/EP2003/004960 WO2004041226A1 (de) | 2002-11-02 | 2003-05-13 | 4-amino-biphenyl-3-ol-derivate enthaltende mittel zum färben von keratinfasern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1562539A1 true EP1562539A1 (de) | 2005-08-17 |
Family
ID=32115138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP03725188A Withdrawn EP1562539A1 (de) | 2002-11-02 | 2003-05-13 | 4-amino-biphenyl-3-ol-derivate enthaltende mittel zum färben von keratinfasern |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7122061B2 (ja) |
| EP (1) | EP1562539A1 (ja) |
| JP (1) | JP2006511496A (ja) |
| AU (1) | AU2003227748A1 (ja) |
| BR (1) | BR0306686A (ja) |
| DE (1) | DE10251106A1 (ja) |
| WO (1) | WO2004041226A1 (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004002604A1 (de) * | 2004-01-15 | 2005-08-04 | Beiersdorf Ag | Visualisierung von Sonnenschutzmitteln auf der Haut |
| DE102004035164A1 (de) | 2004-07-20 | 2006-02-09 | Wella Ag | Neue o-Aminophenol-Derivate und diese Verbindungen enthaltende Färbemittel |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH479670A (de) * | 1964-09-01 | 1969-10-15 | Ciba Geigy | Verwendung von neuen 6-Phenylbenzolylverbindungen als optische Aufhellmittel ausserhalb der Textilindustrie |
| DE2833989A1 (de) * | 1978-08-03 | 1980-02-21 | Wella Ag | Mittel zum faerben von haaren |
| US6262113B1 (en) * | 1996-03-20 | 2001-07-17 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6380235B1 (en) * | 1999-05-04 | 2002-04-30 | American Home Products Corporation | Benzimidazolones and analogues |
| DE10141722A1 (de) * | 2001-08-25 | 2003-03-06 | Wella Ag | 3-Aminophenol-Derivate enthaltende Oxidationshaarfärbemittel sowie neue 3-Aminophenol-Derivate |
-
2002
- 2002-11-02 DE DE10251106A patent/DE10251106A1/de not_active Withdrawn
-
2003
- 2003-05-13 AU AU2003227748A patent/AU2003227748A1/en not_active Abandoned
- 2003-05-13 US US10/501,833 patent/US7122061B2/en not_active Expired - Fee Related
- 2003-05-13 WO PCT/EP2003/004960 patent/WO2004041226A1/de active Application Filing
- 2003-05-13 JP JP2004548708A patent/JP2006511496A/ja not_active Withdrawn
- 2003-05-13 EP EP03725188A patent/EP1562539A1/de not_active Withdrawn
- 2003-05-13 BR BR0306686-0A patent/BR0306686A/pt not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2004041226A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2006511496A (ja) | 2006-04-06 |
| US7122061B2 (en) | 2006-10-17 |
| AU2003227748A1 (en) | 2004-06-07 |
| WO2004041226A1 (de) | 2004-05-21 |
| US20050155160A1 (en) | 2005-07-21 |
| BR0306686A (pt) | 2004-12-07 |
| DE10251106A1 (de) | 2004-05-19 |
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