AU2006200042A1 - Dyeing agents for keratin fibers, containing (1,1'-biphenyl)-2,4-diamine derivatives, and new (1,1'-biphenyl)-2,4-diamine derivatives - Google Patents
Dyeing agents for keratin fibers, containing (1,1'-biphenyl)-2,4-diamine derivatives, and new (1,1'-biphenyl)-2,4-diamine derivatives Download PDFInfo
- Publication number
- AU2006200042A1 AU2006200042A1 AU2006200042A AU2006200042A AU2006200042A1 AU 2006200042 A1 AU2006200042 A1 AU 2006200042A1 AU 2006200042 A AU2006200042 A AU 2006200042A AU 2006200042 A AU2006200042 A AU 2006200042A AU 2006200042 A1 AU2006200042 A1 AU 2006200042A1
- Authority
- AU
- Australia
- Prior art keywords
- group
- amino
- diamino
- diamine
- methyl
- 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.)
- Abandoned
Links
- AXTSDCSKRWMCRQ-UHFFFAOYSA-N 4-phenylbenzene-1,3-diamine Chemical class NC1=CC(N)=CC=C1C1=CC=CC=C1 AXTSDCSKRWMCRQ-UHFFFAOYSA-N 0.000 title claims description 25
- 102000011782 Keratins Human genes 0.000 title claims description 7
- 108010076876 Keratins Proteins 0.000 title claims description 7
- 239000000835 fiber Substances 0.000 title claims description 7
- 239000000975 dye Substances 0.000 title description 25
- 210000004209 hair Anatomy 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000003086 colorant Substances 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 12
- 230000001590 oxidative effect Effects 0.000 claims description 11
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 238000004043 dyeing Methods 0.000 claims description 9
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 239000000982 direct dye Substances 0.000 claims description 5
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical group NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 101100244083 Arabidopsis thaliana PKL gene Proteins 0.000 claims description 4
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- ALQKEYVDQYGZDN-UHFFFAOYSA-N 2-amino-6-methylphenol Chemical compound CC1=CC=CC(N)=C1O ALQKEYVDQYGZDN-UHFFFAOYSA-N 0.000 claims description 3
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 claims description 3
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
- QATYIMPCPNRMMU-UHFFFAOYSA-N 4-(4-methoxyphenyl)benzene-1,3-diamine Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N)C=C1N QATYIMPCPNRMMU-UHFFFAOYSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- GZVVXXLYQIFVCA-UHFFFAOYSA-N 2,3-dimethylbenzene-1,4-diamine Chemical compound CC1=C(C)C(N)=CC=C1N GZVVXXLYQIFVCA-UHFFFAOYSA-N 0.000 claims description 2
- BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 claims description 2
- KEEQZNSCYCPKOJ-UHFFFAOYSA-N 2,6-diethylbenzene-1,4-diamine Chemical compound CCC1=CC(N)=CC(CC)=C1N KEEQZNSCYCPKOJ-UHFFFAOYSA-N 0.000 claims description 2
- MJAVQHPPPBDYAN-UHFFFAOYSA-N 2,6-dimethylbenzene-1,4-diamine Chemical compound CC1=CC(N)=CC(C)=C1N MJAVQHPPPBDYAN-UHFFFAOYSA-N 0.000 claims description 2
- KULOFVMDAJSPOK-UHFFFAOYSA-N 2-(2,5-diaminophenoxy)ethanol Chemical compound NC1=CC=C(N)C(OCCO)=C1 KULOFVMDAJSPOK-UHFFFAOYSA-N 0.000 claims description 2
- YATFNFXGMVOFKB-UHFFFAOYSA-N 2-(aminomethyl)benzene-1,4-diamine Chemical compound NCC1=CC(N)=CC=C1N YATFNFXGMVOFKB-UHFFFAOYSA-N 0.000 claims description 2
- AVKBLCWBDLLVRL-UHFFFAOYSA-N 2-(methoxymethyl)benzene-1,4-diamine Chemical compound COCC1=CC(N)=CC=C1N AVKBLCWBDLLVRL-UHFFFAOYSA-N 0.000 claims description 2
- MGLZGLAFFOMWPB-UHFFFAOYSA-N 2-chloro-1,4-phenylenediamine Chemical compound NC1=CC=C(N)C(Cl)=C1 MGLZGLAFFOMWPB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- FKHKSWSHWLYDOI-UHFFFAOYSA-N 2-phenylbenzene-1,4-diamine Chemical group NC1=CC=C(N)C(C=2C=CC=CC=2)=C1 FKHKSWSHWLYDOI-UHFFFAOYSA-N 0.000 claims description 2
- GCNUGWIBKQDYGG-UHFFFAOYSA-N 2-thiophen-2-ylbenzene-1,4-diamine Chemical compound NC1=CC=C(N)C(C=2SC=CC=2)=C1 GCNUGWIBKQDYGG-UHFFFAOYSA-N 0.000 claims description 2
- HUGIREQZMZZHCH-UHFFFAOYSA-N 2-thiophen-3-ylbenzene-1,4-diamine Chemical compound NC1=CC=C(N)C(C2=CSC=C2)=C1 HUGIREQZMZZHCH-UHFFFAOYSA-N 0.000 claims description 2
- KTVLSQLSQPVCRE-UHFFFAOYSA-N 3-(2,4-diaminophenyl)phenol Chemical compound NC1=CC(N)=CC=C1C1=CC=CC(O)=C1 KTVLSQLSQPVCRE-UHFFFAOYSA-N 0.000 claims description 2
- OOPSLCPMKBRAKI-UHFFFAOYSA-N 4-(2,4-diaminophenyl)phenol Chemical compound NC1=CC(N)=CC=C1C1=CC=C(O)C=C1 OOPSLCPMKBRAKI-UHFFFAOYSA-N 0.000 claims description 2
- RGKJLNMYCNSVKZ-UHFFFAOYSA-N 4-amino-2-(methoxymethyl)phenol Chemical compound COCC1=CC(N)=CC=C1O RGKJLNMYCNSVKZ-UHFFFAOYSA-N 0.000 claims description 2
- MXJQJURZHQZLNN-UHFFFAOYSA-N 4-amino-2-fluorophenol Chemical compound NC1=CC=C(O)C(F)=C1 MXJQJURZHQZLNN-UHFFFAOYSA-N 0.000 claims description 2
- HDGMAACKJSBLMW-UHFFFAOYSA-N 4-amino-2-methylphenol Chemical compound CC1=CC(N)=CC=C1O HDGMAACKJSBLMW-UHFFFAOYSA-N 0.000 claims description 2
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 claims description 2
- ZFIQGRISGKSVAG-UHFFFAOYSA-N 4-methylaminophenol Chemical compound CNC1=CC=C(O)C=C1 ZFIQGRISGKSVAG-UHFFFAOYSA-N 0.000 claims description 2
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 claims description 2
- UOWYGPTYSRURDP-UHFFFAOYSA-N 4-n,4-n-dipropylbenzene-1,4-diamine Chemical compound CCCN(CCC)C1=CC=C(N)C=C1 UOWYGPTYSRURDP-UHFFFAOYSA-N 0.000 claims description 2
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 claims description 2
- MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- WFXLRLQSHRNHCE-UHFFFAOYSA-N 2-(4-amino-n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=C(N)C=C1 WFXLRLQSHRNHCE-UHFFFAOYSA-N 0.000 claims 1
- UEWPUMVXPDOGGA-UHFFFAOYSA-N 2-pyridin-3-ylbenzene-1,4-diamine Chemical compound NC1=CC=C(N)C(C=2C=NC=CC=2)=C1 UEWPUMVXPDOGGA-UHFFFAOYSA-N 0.000 claims 1
- RGMCBPMSFORCJH-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)benzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1C1=CC=C(OCO2)C2=C1 RGMCBPMSFORCJH-UHFFFAOYSA-N 0.000 claims 1
- DHKIYDNMIXSKQP-UHFFFAOYSA-N 4-amino-3-(hydroxymethyl)phenol Chemical compound NC1=CC=C(O)C=C1CO DHKIYDNMIXSKQP-UHFFFAOYSA-N 0.000 claims 1
- 241000031711 Cytophagaceae Species 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 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 claims 1
- -1 2'-chlorobiphenyl-2,4-d Chemical compound 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 description 17
- 238000001819 mass spectrum Methods 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000004040 coloring Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 239000007800 oxidant agent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000000118 hair dye Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 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
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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- 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
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 239000002453 shampoo Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 3
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 3
- 229940018563 3-aminophenol Drugs 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000015165 citric acid Nutrition 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- FXXMDJFRMDVSCF-RXSVEWSESA-N (2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one;hydrate Chemical compound O.OC[C@H](O)[C@H]1OC(=O)C(O)=C1O FXXMDJFRMDVSCF-RXSVEWSESA-N 0.000 description 2
- 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
- CQPNUVOYDSRIIC-UHFFFAOYSA-N 4-(3-methoxy-5-methylphenyl)benzene-1,3-diamine Chemical compound COC1=CC(C)=CC(C=2C(=CC(N)=CC=2)N)=C1 CQPNUVOYDSRIIC-UHFFFAOYSA-N 0.000 description 2
- GPMWAWDEZPFUTN-UHFFFAOYSA-N 4-fluoro-6-methylbenzene-1,3-diamine Chemical compound CC1=CC(F)=C(N)C=C1N GPMWAWDEZPFUTN-UHFFFAOYSA-N 0.000 description 2
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 description 2
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- 125000000129 anionic group Chemical group 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
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- 239000000470 constituent Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 150000002191 fatty alcohols 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
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
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- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000004988 m-phenylenediamines Chemical class 0.000 description 2
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- JQVAPEJNIZULEK-UHFFFAOYSA-N 4-chlorobenzene-1,3-diol Chemical compound OC1=CC=C(Cl)C(O)=C1 JQVAPEJNIZULEK-UHFFFAOYSA-N 0.000 description 1
- NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical compound OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 description 1
- SGNZYJXNUURYCH-UHFFFAOYSA-N 5,6-dihydroxyindole Chemical compound C1=C(O)C(O)=CC2=C1NC=C2 SGNZYJXNUURYCH-UHFFFAOYSA-N 0.000 description 1
- FIRYIQMUIDKJMT-UHFFFAOYSA-N 5-(2,4-diaminophenyl)-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C1=CC=C(N)C=C1N FIRYIQMUIDKJMT-UHFFFAOYSA-N 0.000 description 1
- UQWHHOZZIGVLHY-UHFFFAOYSA-N 5-(2,4-diaminophenyl)-2-methylphenol Chemical compound C1=C(O)C(C)=CC=C1C1=CC=C(N)C=C1N UQWHHOZZIGVLHY-UHFFFAOYSA-N 0.000 description 1
- BXSADNUHBQZYEZ-UHFFFAOYSA-N 5-(2,4-diaminophenyl)benzene-1,3-diol Chemical compound NC1=CC(N)=CC=C1C1=CC(O)=CC(O)=C1 BXSADNUHBQZYEZ-UHFFFAOYSA-N 0.000 description 1
- CNEHJJGZSQRWRR-UHFFFAOYSA-N 5-amino-2-(2-hydroxyethoxy)phenol Chemical compound NC1=CC=C(OCCO)C(O)=C1 CNEHJJGZSQRWRR-UHFFFAOYSA-N 0.000 description 1
- SZNMBMXMWVVCOE-UHFFFAOYSA-N 5-amino-2-ethylphenol Chemical compound CCC1=CC=C(N)C=C1O SZNMBMXMWVVCOE-UHFFFAOYSA-N 0.000 description 1
- WDQMXRWYXILWPT-UHFFFAOYSA-N 5-amino-4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=C(N)C=C1O WDQMXRWYXILWPT-UHFFFAOYSA-N 0.000 description 1
- HEAQOCBITATQEW-UHFFFAOYSA-N 5-amino-4-fluoro-2-methylphenol Chemical compound CC1=CC(F)=C(N)C=C1O HEAQOCBITATQEW-UHFFFAOYSA-N 0.000 description 1
- ATCBPVDYYNJHSG-UHFFFAOYSA-N 6-methoxy-2-n-methylpyridine-2,3-diamine Chemical compound CNC1=NC(OC)=CC=C1N ATCBPVDYYNJHSG-UHFFFAOYSA-N 0.000 description 1
- WEPOCTWSRWLQLL-UHFFFAOYSA-N 6-methoxypyridine-2,3-diamine Chemical compound COC1=CC=C(N)C(N)=N1 WEPOCTWSRWLQLL-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- JSFUMBWFPQSADC-UHFFFAOYSA-N Disperse Blue 1 Chemical compound O=C1C2=C(N)C=CC(N)=C2C(=O)C2=C1C(N)=CC=C2N JSFUMBWFPQSADC-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 229910002666 PdCl2 Inorganic materials 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- JLUQMLDFFPAEAN-UHFFFAOYSA-N S(=O)(=O)(O)O.NC1=C(C)C=C(C=C1)N.S(=O)(=O)(O)O.NC=1C=NN(C1N)CCO Chemical compound S(=O)(=O)(O)O.NC1=C(C)C=C(C=C1)N.S(=O)(=O)(O)O.NC=1C=NN(C1N)CCO JLUQMLDFFPAEAN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000610375 Sparisoma viride Species 0.000 description 1
- 229920002472 Starch Chemical class 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000005211 alkyl trimethyl ammonium group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940101006 anhydrous sodium sulfite Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- VYVWSBDWOZVPGB-UHFFFAOYSA-N benzene;benzene-1,4-diamine Chemical compound C1=CC=CC=C1.NC1=CC=C(N)C=C1 VYVWSBDWOZVPGB-UHFFFAOYSA-N 0.000 description 1
- 150000005130 benzoxazines Chemical class 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Chemical class 0.000 description 1
- 229920002678 cellulose Chemical class 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229940107161 cholesterol Drugs 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000000490 cosmetic additive Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 125000004990 dihydroxyalkyl group Chemical group 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- OJLOUXPPKZRTHK-UHFFFAOYSA-N dodecan-1-ol;sodium Chemical compound [Na].CCCCCCCCCCCCO OJLOUXPPKZRTHK-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- VGSVNUGKHOVSPK-UHFFFAOYSA-N leukoaminochrome Chemical compound C1=C(O)C(O)=CC2=C1NCC2 VGSVNUGKHOVSPK-UHFFFAOYSA-N 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 1
- 229960004963 mesalazine Drugs 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- HFOJRTIFHRRHGA-UHFFFAOYSA-N naphthalen-1-ol;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC=C2C(O)=CC=CC2=C1 HFOJRTIFHRRHGA-UHFFFAOYSA-N 0.000 description 1
- ZUVBIBLYOCVYJU-UHFFFAOYSA-N naphthalene-1,7-diol Chemical compound C1=CC=C(O)C2=CC(O)=CC=C21 ZUVBIBLYOCVYJU-UHFFFAOYSA-N 0.000 description 1
- JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000001005 nitro dye Substances 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 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
- 239000003208 petroleum Substances 0.000 description 1
- 229960003742 phenol Drugs 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
- 235000011056 potassium acetate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 229940001482 sodium sulfite Drugs 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000008107 starch Chemical class 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Cosmetics (AREA)
Description
I 1
AUSTRALIA
Patents Act COMPLETE SPECIFICATION
(ORIGINAL)
Class Int. Class Application Number: Lodged: Complete Specification Lodged: Accepted: Published: Priority Related Art: Name of Applicant: P&G-Clairol, Inc.
Actual Inventor(s): Laurent Chassot, Hans-Jurgen Braun Address for Service and Correspondence: PHILLIPS ORMONDE FITZPATRICK Patent and Trade Mark Attorneys 367 Collins Street Melbourne 3000 AUSTRALIA Invention Title: 6 a DYEING AGENTS FOR KERATIN FIBERS, CONTAINING (1,1'-BIPHENYL)-2,4-DIAMINE DERIVATIVES, AND NEW (1,1'-BIPHENYL)-2,4-DIAMINE DERIVATIVES Our Ref: 763293 POF Code: 103357/460664 The following statement is a full description of this invention, including the best method of performing it known to applicant(s): -1-
I
I I
DESCRIPTION
DYEING AGENTS FOR KERATIN FIBERS, CONTAINING (1,1'-BIPHENYL)- 2,4-DIAMINE DERIVATIVES, AND NEW (1,1'-BIPHENYL)- 2,4-DIAMINE DERIVATIVES The present application is a divisional application from Australian patent application number 2002210494, the entire disclosure of which is incorporated herein by reference.
The present invention relates to agents for oxidative dyeing of keratin fibers, particularly human hair, based on a developer/coupler combination which contains a (1,1 '-biphenyl)-2,4-diamine derivative-as the coupler, and to new (1,1 '-biphenyl)-2, 4 diamine derivatives.
In the area of keratin fiber dyeing, particularly hair dyeing, oxidation dyes have attained substantial importance. In this case, the coloration is produced by reaction of certain developers with certain couplers in the presence of an appropriate oxidant.
Suitable developers are, in particular, 2,5-diaminotoluene, alcohol, p-aminophenol, 4,5-diamino-1-(2'-hydroxyethyl)pyrazole and 1,4-diaminobenzene, and suitable couplers are, for example, resorcinol, 2-methylresorcinol, 1naphthol, 3-aminophenol, m-phenylenediamine, 2-amino-4-(2'-hydroxyethyl)aminoanisole, 1,3-diamino-4-(2'-hydroxyethoxy)benzene and 2,4-diamino-5-fluorotoluene.
The oxidation dyes used for dyeing human hair must meet numerous requirements in addition to that of being able to produce colorations of the desired intensity. For example, these dyes must be harmless from a toxicological and dermatological standpoint, and the hair colorations obtained must have good light fastness, resistance to permanent waving, acid fastness and rubbing fastness. In any case, however, in the absence of exposure to light, rubbing and chemicals, such colorations must remain stable over a period of at least 4 to 6 weeks. Moreover, by combining appropriate developers and couplers, it must be possible to create a wide range of different color shades.
Attempts have already been made to improve the properties of m-phenylenediamines by introduction of substituents. In this regard, the reader is referred to German Unexamined Patent Application DE 30 28 131 which, among other things, also describes dyeing agents which as couplers contain special m-phenylenediamines alkylsubstituted in the 4-position.
2 With the currently known dyeing agents, however, it is not possible to meet the requirements placed on such agents in all respects. Hence, the need continued to exist for novel couplers that would meet the aforesaid requirements to a particularly high degree.
We have now found that by use of (1,1 '-biphenyl)-2,4-diamine derivatives of general formula intense, stable blue color shades can be obtained in addition to natural and purple or violet shades.
Hence, the object of the present invention is an agent for oxidative dyeing of keratin fibers, for example wool, furs, feathers or hair, particularly human hair, which agent is based on a developer-coupler combination that is characterized by the fact that it contains as the coupler at least one (1,1 '-biphenyl)-2,4-diamine derivative of formula or a physiologically tolerated salt thereof R3 R2 R4 Ri
HN
H. (I)
NH
2 wherein R1, R2, R3, R4 and R5 can be equal or different and independently of each other denote hydrogen, a halogen atom (fluorine, chlorine, bromine, iodine), a cyano group, a hydroxyl group, a C 1
-C
4 -alkoxy group, a C 1
-C
4 -hydroxyalkoxy group. a Ci-C6-alkyl group, a C 1
-C
4 -alkyl thioether group, a mercapto group, a nitro group, an amino group
(NH
2 a C 1
-C
4 -monoalkylamino group, a di(C 1
-C
4 )-alkylamino group, a trifluoromethyl group, a -C(O)H group, a -C(O)CH 3 group, a -C(O)CF 3 group, an -Si(CH 3 3 group, a
C,-C
4 -hydroxyalkyl group, a C 2
-C
4 -dihydroxyalkyl group, a -CH= CHR6 group, a
-(CH
2 )p-CO 2 R7 group or a -(CH 2 )p-R8 group with p 1, 2, 3 or 4, a -C(R9)=NR10 group or a C(R12)H-NR13R14 group, or two adjacent R1 to R5 groups form an
-O-CH
2 -O bridge; R6 denotes hydrogen, a nitro group, a C0 2 R7 group or a -C(O)0H 3 group; R7, R9 and R12 can be equal or different and independently of each other denote hydrogen or a Cl-C 4 -alkyl group; R8 denotes an amino or nitrile group; RiO, R13 and R14 can be equal or different and independently of each other denote hydrogen, a hydroxyl group, a Cl-C 4 -alkyl group, a Cl-C 4 -hydroxyalkyl group, a C 2
-C
4 dihydroxyalkyl group or a group of formula /Rli and Ri 1 denotes hydrogen, an amino group or a hydroxyl group.
Noteworthy among the compounds of formula are, for example: biphenyl-2,4-diamine; 4-benzo[1 ,3jdioxol-5-ylbenzene-1 ,3-diamine; 2'-(2-hydroxyethyl) biphenyl-2,4-diamine; 2'-acetyl bi phe nyl- 2,4-d ia mine; 2'-aminobiphenyl-2,4diamine; 2'-bromobiphenyl-2,4-diamine; 2'-chlorobiphenyl-2,4-d ia mine; 2'-cyanobiphenyl-2,4-diamine; 2'-ethylbi phe nyl- 2,4-d ia mine; 2'-fluorobiphenyl-2,4-diamine; 2'-hydroxybiphenyI-2,4-diamine; 2'-methoxybiphenyl-2,4-d ia mine; 2'-methylbiphenyl-2,4-diamine; 2'-methylsulfanylbiphenyl-2,4-diamine; 2'-nitrobiphenyl-2,4-diamine; 2'-trifluoromethylbiphenyl-2,4-diamine; (2-hyd roxyethyl) bi phenyl-2,4-d ia mine; 3'acetylbiphenyl-2,4-diamine; 3'-aminobiphenyl-2,4-diamine; 3'-bromobiphenyl-2,4diamine; 3'-chlorobiphenyl-2,4-diamine; 3'-cyanobiphenyl-2,4-diamine; 3'-ethylbiphenyl-2,4-d ia mine; 3'-.fluorobiphenyl-2,4-diamine; 3'-hydroxybiphenyl-2,4-diamine; 3'-methoxybiphenyl-2,4-diamine; 3'-methylbiphenyl-2,4-diamine; 3'-methylsulfanylbiphenyl-2,4-diamine; 3'-nitrobiphenyl-2,4-diamine; 3'-trifluoromethylbiphenyl-2,4diamine; 4'-(2-hydroxyethyl)biphenyl-2,4-diamine; 4'-acetylbiphenyl-2,4-d ia mine; 4'ami nobiphenyl- 2,4-d ia mine; 4'-bromobiphenyl-2,4-diamine; 4'-chlorobiphenyl-2,4diamine; 4'-cyanobiphenyl-2,4-diamine; 4'-ethylbiphenyl-2,4-d ia mine; 4'-fluorobiphe nyl-2,4-d ia mine; 4'-hydroxybiphenyl-2,4-diamine; 4'-methoxybiphenyl-2,4-diamine; 4'-methylbip henyl-2,4-d ia mine; 4'-methyls ulf anyl bi phe nyl-2,4-d ia mine; 4'-nitrobiphenyl-2,4-dia mine; 4'-trifluoromethylbiphenyl-2,4-diamine; 2'-amino-3'-aminob iphenyl-2,4-dianline; 2'-amino-3'-hyd roxybiphenyl-2,4-d iamine; 2'-amino-3'-methoxybiphenyl-2,4-d ia mine; 2'-amino-3'-methylbiphenyl-2,4-diamine; 2'-arnino-4'-aminobiphenyl-2,4-diamine; 2'-amino-4'-hydroxybiphenyl-2,4-diamine; 2'-amino'-4'methoxybiphenyl-2,4-diamine; 2'-ami no-4'- methyl bi phenyl-2,4-d ia mine; 4 aminobipheflyl-2,4-diamile; 2'-ami no-5'-hyd roxybiphefyl- 2,4dia mine; methoxybiphefl2,4-diamile; 2'-a mino-5'-methylbiphelY- 2,4-dia mine; 2'-amino-6'aminobipheflyl-2,4-diamile; 2'-amino-6'-hydroxybiphefyl-2,4diamine; 2'-amino-6'methoxybiphelyl-2,4-diamile; 2'-amino-6'-methylbipheflY-2,4diamine; 2'-hydroxy-3'aminobiphenyl-2,4-diamile; 2'-hyd roxy-3'-hyd roxybiphefyly2,4-dia mine; 2'-hyd roxy- 3'-methoxybiphefl-2,4-diamile; 2'-hydroxy-3'-methylbiphefl-2,4-diamile; 2'-hydroxy-4'-aminobiphefl-2,4-diamifle;2'-hyd roxy-4'-hydroxybiphefl2,4-diamifle; 2 1 hyd roxy-4'-methoxybiphefnlYI2,4-dia mine; 2'-hydroxy-4'-methylbiphefl-2,4-diamine; 2'-hydroxy-5'-amiflobipheflY2,4-diamine; 2,4-diamine; 2'-hydroxy-5'-methoxybiphel-2,4-diamile; biphenyl-2,4-diamile; 2'-hydroxy-6'-amiflobipheflY-2,4-diamile; 2'-hydroxy-6'-hyd roxybipheflyl-2,4-diamifle;2'-hydroxy-6'-methoxybipheflY-2,4-diamifle;2'-hydroxy- 6.'-methylbiphefl-2,4-diafifle; 2'-methoxy-3'-amiflobipheflY2,4-diamine; 2'methoxy-3'-hyd rQxybi phefnlYI2,4-dia mine; 2'-methoxy-3'-nmethoxybiphefly2,4-diamine; 2'-methoxy-3'-methylbipheflY2,4-diamile; 2'-methoxy-4'-anobiphel-2,4diamine; 2'-methoxy-4'-hydroxybiphefylY2,4-diamine; 2'-methoxy-4'-methoxybiphe nyl- 2,4-d iamine; 2'-methoxy-4'-methylbiphefl-2,4-dia mine; aminobipheflyl-2,4-diamile; 2'-methoxy-5'-hydroxybiphefly2,4-diamile; 2'-methoxy-5'-methoxybiphel-2,4-diamile; 2'-methoxy-5'-methyl bi phefl-2,4-d iamine; 2'-methoxy-6'-amiflobiphefl-2,4-diamine; 2'-methoxy-6'-hydroxybiphefl2,4diamine; 2'-methoxy-6'-methQxybiphefylY2,4-diamine; 2'-methoxy-6'-methylbipheflyI-2,4-diamine; 2'-methyI-3'-aminobiphenyl-2,4-diamine; 2'-methyl-3'-hydroxybiphenyl-2,4-d ia mine; 2'-methyl-3'-methoxybiphenyk2,4-diamine; 2'-methyl-3'-methylbiphenyl-2,4-d ia mine; 2'-methyI-4'-aminobiphenyk2,4-diamine; 2'-methyl-4'-hydroxybiphenyl-2,4-diamine; 2'-methyl-4'-methoxybipheny-2,4dia mine; 2'-methyl- 4'-methylbiphenyl-2,4-diamine; 2'-methyl-5'-aminobiphenyI-2,4-diamine; hydroxybiphenyl-2,4-diamine; 2'-methyI-5'-Mnethoxybipheny-2,4diamine; 2'-methyl- 5'-methylbiphenyl-2,4-diamine; 2'-methyl-6'-aminobiphenyI-2,4-dia mine; 2'-methyl-6'hyd roxybiphenyl-2,4-d ia mine; 2'-methyl-6'-methoxybip he ny-2,4-dia mine; 2'-methyl- 6'-methylbi phenyI-2,4-d ia mine; 3'-amino-4'-aminobipheny-2,4-diamine; 3'-amino-4'hydroxybiphenyl-2,4-diamine; 3'-amino-4'-methoxybiphenyl- 2,4-dia mine; 3-amino- 4'-methylbiphenyI-2,4-diamine; 3'-amino-5'-aminobipheny-2,4-diamine; 3'-aminoroxybiphenyl-2,4-diamine; 3'-amino-5'-methoxybiphenyl-2,4-diamile; 3'-amino-5'-methylbiphenyl-2,4-diamine; 3'hyd roxy-4'-ami nobi phe nyl-2,4-d ia mine; 3-hyd roxy-4'-hyd roxybi phenl-l2,4-dia mine; 3'-hydroxy-4'-methoxybiphenyl-2, 4 -diamine; 3'-hydroxy-4'-methylbiphenyl-2,4-diamine; 3'-hydroxy-5'-aiobiphelyl- 2 4 diamine; 3'-hydroxy-5'-hydroxybiphenyl2,4-diamine; yl-2,4-diamine; 3'-hyd roxy-5'-methyl biphenyl2,4-dia mine; 3'-methoxy-4'-amilobiphenyl-2,4-diamile; 3I-methoxy-4'-hydroxybiphenyl2, 4 -diamine; 3'-methoxy-4'-methoxybiphenyl-2,4-diamile; 3'-methoxy-4'-methylbiphenyl-2,4-diamine; 3'-methoxy- 5'-aminobipheflyl-2,4-diamine; 3'-methoxy-5'-hydroxybiphenyl2,-diamine; 3'- '-methoxybiphenyl-2,4-diamifle; 3'-methoxy-5'-methylbiphenyl-2,4-diamine; 3'-methyl-4'-aminobiphenyl-2,4-diamine; 3'-methyl-4'-hydroxybiphefl2,4-diamine; 3'-methyl-4'-methoxybiphenyl2,4-diamine; 3'-methyl-4'-nmethylbiphenyl-2, 4 -diamine; 3'-methyl- 5'-aminobi phefl-2,4-dia mine; 3'-methyl-5'-hydroxybiphenyl- 2 4 diamine; 3'-methyl-5'-methoxybiphenyl2,4-diamine and yl-2,4-diamine, as well as the physiologically tolerated salts thereof.
Preferred compounds of formula or their physiologically tolerated salts are those wherein at least three of the R1 to R5 groups denote hydrogen or (ii) three of the R1 to R5 groups denote hydrogen and the two remaining groups independently of each other denote hydrogen, a methoxy group, a hydroxyl group, a Cl-C 4 -alkyl group, a Cl-C 4 -hydroxyalkyI group or an amino group, or when the two remaining groups are adjacent to each other they together form an -O-CH 2 bridge.
Particularly preferred are the following (1 ,1 '-biphenyl)-2,4-diamine derivatives of formula biphenyl-2,4-diamine; 4-benzo[1l,3]dioxol-5-ylbenzene-1 ,3-diamine; 4'hyd roxybi phenyl-2,4-d ia mine; 4'-aminobiphenyl-2,4-diamine; 3'-hydroxybiphelyl- 2,4-diamine; 4'-methoxybiphenyl-2,4-diamine and the physiologically tolerated salts thereof.
The compounds of formula can be used as the free bases as well as in the form of their physiologically tolerated salts with inorganic or organic acids, for example hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, propionic acid, lactic acid or citric acid.
The colorant of the invention contains the (1,1'-biphenyl)-2,4-dia mine derivatives of formula in a total amount from about 0.005 to 20 wt. an amount of about 0.01 to 5 wt.% and especially 0.1 to 2.5 wt.% being preferred.
V I 6 Suitable developers are all those developers that are known to be used with, and are appropriate for, such colorants, for example 1 ,4-d iami no benzene (p-phenylenediamine), 1 ,4-diamino-2-methylbenzene (p-toluylened ia mine), 1 ,4-diamino-2,6-dimethylbenzene, 1 ,4-diamino-3,5-diethylbenzene, 1 ,4-diamino-2,5-dimethylbenzene, 1 ,4-diamino-2,3-dimethylbenzene, 2-chloro-1 ,4-diaminobenzene, 1 ,4-diamino-2- (thiophen-2-yl) benzene, 1 ,4-diamino-2-(thiophen-3-yl) benzene, 1 ,4-diamino-2-(pyrid in-3-yl) benzene, 2, 5-diaminobiphenyl; 1 ,4-diamino-2-methoxymethylbenzene, 1 ,4diamino-2-aminomethylbenzene, 1 ,4-diamino-2-hydroxymethylbenzene, 1 ,4-diamino-2- (2-hyd roxyethoxy) benzene, 1 -(2,5-diaminophenyl)ethanol, 2-[2-(acetylamino)ethoxyl-1 ,4-diaminobenzene, 4-phenylaminoaniline, 4-dimethylaminoaniline, 4-diethylaminoaniline, 4-dipropylaminoaniline, 4-[ethyl-,(2-hydroxyethyl)aminolaniline, 4-l[di(2hydroxyethyl)aminolaniline, i(2hyd roxyethyl)ami no]- 2-nethyla niline, 4- [2-methoxyethyl)a minollani line, 4-[(3-hydroxypropyl)aminolaniline, 4-[(2,3-dihydroxypropyl)aminolaniline, 1 ,4-diamino-2-(2-hydroxyethyl) benzene, 1 ,4-diamino-2-(1-methylethyl)benzene, 1 ,3-bis-[(4-aminophenyl)(2-hydroxyethyl)anminoh-2Propanol, 1 ,4-bis-[(4aminophenyl)a mi no] butane, 1 ,8-bis-(2, 5-diaminophenoxy)-3, 6-dioxaoctane,4-aminophenol, 4-amino-3-methylphenol, 4-ami no-3-(hyd roxymethyl) phenol, 4-amino-3-fluorophenol, 4-methylaminophenol, 4-amino-2-(aminomethyl) phenol, 4-amino-2-(hydroxymethyl) phenol, 4-amino-2-fluorophenol, 4-amino-2-[ (2-hyd roxyethyl) amino]methylphenol, 4-amino-2-methylphenol, 4-amino-2-(methoxymethyl) phenol, 4-amino- 2-(2-hyd roxyethyl) phenol, 5-aminosalicylic acid, 2,5-diaminopyridine, 2,4,5',6tetraaminopyrimidine, 2,5,6-triamino-4-(l H)-pyrimidone, 4,5-diamino-1 hydroxyethyl)-l1H-pyrazole, 4, 5-diamino-1 -methylethyl)-1 H-pyrazole, 4, 5-diamino-1 [(4-methylphenyl)methyl]-1 H-pyrazole, 1 -[(4-chlorophenyl)methyl]-4,5-diamino-1
H-
pyrazole, 4, 5-diamino-1 -methyl-i H-pyrazole, 4, 5-diamino-3-methyl-1 -methyl-i H-pyrazole, 4, 5-diamino-3-methyl-1 -methyl-i H-pyrazole [sic Translator], 2-aminophenol, 2-amino-6-methyl phenol and Moreover, the colorant of the invention can optionally also contain other known couplers, for example 2,6-diaminopyridine, 2-amino-4-[(2-hydroxyethyl)aminolanisole, 2,4-diamino-1 -fluoro-5-methylbenzene, 2,4-diamino-1 zene, 2,4-diamino-l1-ethoxy-5-methylbenzene, 2,4-diamino-l1-(2-hydroxyethoxy)-5methylbenzene, 2,4-di[(2-hydroxyethyl)aminol- 1,5-dimethoxybenzene, 2,3-diamino- 6-methoxypyridine, 3-amino-6-methoxy-2-(methylamino)pyridine, 2,6-diamino-3,5dimethoxypyridifle, 3,5-diamino-2,6-dimethoxypyridifle, 1 ,3-diaminobenzene, 2,4-diamnino-i -(2-hydroxyethoxy)benzefle, 2,4-d iamino-i 1,5-di(2-hyd roxyethoxy) benzene, 1 -(2-aminoethoxy)-2,4-diaminobenzefle, 2-amino-i -(2-hydroxyethoxy)-4-methylamiflobenzene, 2,4-diamilopheloxyacetiC acid, 3-lfdi(2-hydroxyethyl)aminolanilifle, 4-amino-2-di[(2-hydroxyethYl)amifl-h -ethoxybenzene, 5-methyl-2-( 1 -methylethyl)phenol, 3-[(2-hydroxyethyl)aminolalilifle, 3-[(2-aminoethyl)aminolalhline, 1 ,3-di(2,4-diaminophenoxy)propafle, di (2,4-d iaminophenoxy) methanle, 1 ,3-diamino-2,4-dimethoxybenzene, 2,6-bis-(2-hydroxyethy)aminotoluefle, 4-hydroxyindole, 3-dimethylaminophenol, 3-diethylaminopheflol, 5-amino-2-methylphenol, 5-amino-4-fluoro-2-methylphenol, 5-amino-4-methoxy-2methylphelol, 5-amino-4-ethoxy-2-methylphelol, 3-amino- 2,4-d ich loro phenlol, 5 -amino-2,4-d ichloro phenlol, 3-amino-2-methylphenol, 3-amino- 2-chloro-6-methylPheflol, 3-aminophenol, 2-j(3-hydroxyphenyl)aminolacetamide, 5-11(2hydroxyethyl)amiflol-2-methylpheflol, 3-[(2-hyd roxyethyl) amino] phenol, methoxyethyl)amino] phenol, 5-amino-2-ethylphenol, 2-(4-amino-2-hydroxyphenoxy)ethanol, 5-[(3-hydroxypropyl)amil-2-methylphenol, 3-[(2,3-dihydroxypropyl)amino]-2-methylphenol, 3-[(2-hydroxyethyl)amifl-2-methylphenol, 2-amino-3-hydroxypyridine, 5-amino-4-chloro-2-methYlphenol, 1 -naphthol, i 1 ,7-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, 2, 7-dihydroxynaphthalene, 2methyl-i -naphthol acetate, 1 ,3-di-hydroxybenzene, 1 -chloro-2,4-dihydroxybenzene, 2-chloro-i ,3-dihydroxybenzene, 1 ,2-dichloro-3,5-dihydroxy-4-methylbenzene, 1 dichloro-2,4-dihydroxybenzene, 1, 3-d ihyd roxy-2-methyl benzenle, 3,4-methylenedioxyphenol, 3,4-methylenedioxyaniline, 5-[(2-hydroxyethyl)amino]- 1,3-benzodioxole, 6-bromo-l1-hydroxy-3,4-methylenedioxybenzefle, 3,4-diaminobenzoic acid, 3,4-dihydro-6-hydroxy-i ,4(2H)benzoxazine, 6-amino-3,4-dihydro- 1,4(2H)-benzoxazine, 3methyl-i -phenyl-5-pyrazolone, 5,6-dihydroxyindole, 5, 6-dihydroxyindoline, droxyindole, 6-hydroxyindole, 7-hydroxyindole and 2,3-indolinedione.
The couplers and developers can be present in the colorant of the invention either individually or in admixture with one another, the total amount of each of the couplers and developers in the colorant of the invention being about 0.005 to 20 wt.% preferably about 0.01 to 5.0 wt.% and particularly 0.1 to 2.5 wt.% (based on the total amount of colorant). The total amount of the developer-coupler combination contained in the colorant described herein is preferably about 0.01 to 20 an amount of about 0.02 to 10 wt.% and especially 0.2 to 6 wt.% being particularly preferred. In general, the developer and the coupler are used in approximately equimolar amounts. In this respect, it is not disadvantageous, however, if the developer is present in a certain excess or deficiency [for example in a (coupler:developer) ratio of 1 2 to 1 Moreover, the colorant of the invention can also contain other dye components, for example 6-amino-2-methylphenol and 2-amino-5-methylphenol, as well as common anionic, cationic, amphoteric or nonionic direct dyes, for example triphenylmethane dyes such as 4-[(4'-aminophenyl)-(4'-imino-2",5"-cyclohexadien-1 "-ylidene)methyl]- 2-methylaminobenzene monohydrochloride (Color Index 42 510) and amino-3'-methylphenyl)-(4"-imino-3"-methyl-2",5"-cycohexadien-1 "-ylidene)methyl]- 2-methylaminobenzene monohydrochloride 42 520), aromatic nitro dyes such as 4-(2'-hydroxyethyl)aminonitrotoluene, 2-amino-4,6-dinitrophenol, 2-amino-5-(2'hydroxyethyl)aminonitrobenzene, 2-chloro-6-(ethylamino)-4-nitrophenol, 4-chloro-N-(2hydroxyethyl)-2-nitroaniline, 5-chloro-2-hydroxy-4-nitroaniline, 2-amino-4-chloro-6nitrophenol and 1-(2'-ureidoethyl)amino-4-nitrobenzene, azo dyes such as, for example, sodium 6-[(4'-aminophenyl)azo]-5-hydroxynaphthalene-1-sulfonate
(C.I.
14 805) and disperse dyes, for example 1,4-diaminoanthraquinone and 1,4,5,8tetraaminoanthraquinone. The colorants of the invention can contain the aforesaid dye components in an amount from about 0.1 to 4 wt.%.
The couplers and developers as well as the other dye components, provided they are bases, can, of course, also be used in the form of their physiologically tolerated salts with organic or inorganic acids, for example hydrochloric acid or sulfuric acid, or if they contain aromatic OH groups in the form of their salts with bases, for example as alkali metal phenoxides.
Moreover, if the colorants of the invention are to be used for coloring hair, they can also contain other common cosmetic additives, for example antioxidants such as ascorbic acid, thio-glycolic acid or sodium sulfite, as well as perfume oils, complexing agents, wetting agents, emulsifiers, thickeners and hair-care agents.
The colorant of the invention can be in the form of, for example, a solution, 9 particularly an aqueous or aqueous-alcoholic solution. A particularly preferred formulation form, however, is a cream, gel or emulsion. Such a composition consists of a mixture of the dye components and the usual additives employed for such compositions.
Common additives to 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, moreover wetting agents or emulsifiers from the classes of anionic, cationic, amphoteric or nonionic surface-active agents, for example fatty alcohol sulfates, ethoxylated fatty alcohol sulfates, alkylsulfonates, alkylbenzenesulfonates, alkyltrimethylammonium salts, alkylbetaines, ethoxylated fatty alcohols, ethoxylated nonylphenols, fatty acid alkanolamides and ethoxylated fatty esters, furthermore thickeners such as the higher fatty alcohols, starch, cellulose derivatives, petrolatum, paraffin oil and fatty acids, also hair-care agents such as cationic resins, lanolin derivatives, cholesterol, pantothenic acid and betaine. The said constituents are used in amounts commonly employed for such purposes, for example the wetting agents and emulsifiers at a concentration of about to 30 the thickeners in an amount from about 0.1 to 25 wt.% and the haircare agents at a concentration from about 0.1 to 5 wt.%.
Depending on the composition, the colorant of the invention can be weakly acidic, neutral or alkaline. In particular, it has a pH of 6.5 to 11.5. Adjustment to a basic pH is preferably done with ammonia, but it can also be done with an organic amine, for example monoethanolamine and triethanolamine, or with an inorganic base such as sodium hydroxide and potassium hydroxide. Suitable for adjustment to an acidic pH are inorganic or organic acids, for example phosphoric acid, acetic acid, citric acid or tartaric acid.
For oxidative dyeing of hair, the afore-described colorant is mixed with an oxidant just before use, and the resulting mixture is applied to hair in an amount sufficient for the hair-dyeing treatment, in general about 50 to 200 grams, depending on the hair fullness. The ready-to-use oxidative hair colorant obtained after mixing with the oxidant preferably has a pH of 6.5 to 11.5.
Suitable oxidants for developing the hair coloration are mainly hydrogen peroxide or its products of addition to urea, melamine, sodium borate or sodium carbonate, in the form of a 3-12%, preferably 6% aqueous solution, atmospheric oxygen also being suitable. When a 6% hydrogen peroxide solution is used as oxidant, the weight ratio of hair colorant to oxidant is from 5 1 to 1 2, but preferably 1 1. Larger amounts of oxidant are used primarily at higher dye concentrations in the hair colorant or when stronger bleaching of the hair is wanted at the same time. The mixture is allowed to act on the hair at 15 to 50 0 C for about 10 to 45 min, preferably 30 min, after which the hair is rinsed with water and dried. Optionally, following this rinsing, the hair is washed with a shampoo and optionally post-rinsed with a weak organic acid, for example citric acid or tartaric acid. The hair is then dried.
The colorants of the invention containing a (1,1'-biphenyl)-2,4-diamine derivative of formula as coupler give hair colorations of excellent color stability, particularly in terms of light fastness, wash fastness and rubbing fastness. As far as the dyeing properties are concerned, the hair colorants of the invention provide a wide range of different color shades from blond to brown, purple, violet and even blue and black, depending on the developer-coupler combination used, the achievable intense and stable blue shades being particularly noterworthy. The very good coloring properties of the hair colorant of the present patent application also manifest themselves in that this colorant makes it possible to dye gray hair, previously not damaged chemically, without any problems and with good covering power.
The (1,1'-biphenyl)-2,4-diamine derivatives of formula can be prepared by known methods of synthesis, for example by methods similar to those described in the practical examples given hereinbelow.
The (1,1 '-biphenyl)-2,4-diamine derivatives of formula are highly water-soluble and give colorations particularly in the blue and purple color range of high color intensity and excellent color stability, particularly in terms of light fastness, wash fastness and rubbing fastness. Moreover, they have excellent storage stability, particularly as constituents of the oxidation colorants described herein.
11 Hence, another object' of the present invention are (1,1'-biphenyl)-2,4-diamine derivatives of general formula (II) R3 R2. ,R4 RI-
H
2
N
NH
2 wherein R1,R2,R3,R4,R5 can be equal or different and independently of each other denote hydrogen, hydrogen [sic Translator], a chlorine atom, a fluorine atom, a cyano group, a hydroxyl group, a C,-C 4 -alkoxy group, a C,-C 4 -hydroxyalkoxy group, a C,-C.-alkyl group, a C,-C 4 -alkyl thioether group, a mercapto group, a nitro group, an amino group
(NH
2 a C 1
-C
4 -monoalkylamino group, a di(C-C 4 )-alkylamino group, a trifluoromethyl group, a -C(O)H group, a -C(O)CH 3 group, a -C(O)CF 3 group, an -Si(CH 3 3 group, a C 1
C
4 -hydroxyalkyl group, a C 2
-C
4 -dihydroxyalkyl group, a -CH= CHR6 group, a -(CH2)p-CO 2 R7 group, a -(CH 2 group with p 1,2,3 or 4, a NR10 group or a C(R1 2)H-NR13R14. group, or two adjacent R1 to R5 groups form an -O-CH 2
-O-
bridge; R6 denotes hydrogen, a nitro group, a C0 2 R7 group or a -C(O)CH 3 group; R7,R9 and R12 can be equal or different and independently of each other denote hydrogen or a C,-C 4 alkyl group; R8 denotes an amino group or a nitrile group; R13 and R14 can be equal or different and independently of each other denote hydrogen, a hydroxyl group, a. C-C 4 -alkyl group, a C 1
-C
4 -hydroxyalkyl group, a C2-C 4 dihydroxyalkyl group or a group having the formula and R11 denotes hydrogen, an amino group or a hydroxyl group; and at least one of the R1 to R5 groups does not denote hydrogen, 1? or the physiologically tolerated salts thereof.
The following examples illustrate the object of the invention in greater detail without limiting its scope.
EXAMPILES
Example 1 A. Synthesis of tert. butyl (4-b romro-3-te rt. butoxvca rbo nvlami nor)henyl)'carba mate To a suspension of 10 g (32.4 mmoles) of tert.butyl (3-tert.butoxycarbonylaminophenyl)carbamate in 100 mL of 1,2-dimethoxyethane was added dropwise at 0 00 over a period of 2 hours a solution of 6 g (33.7 mmoles) of N-bromosuccinimide in mL of 1,2-dimethoxyethane. The reaction mixture was then allowed to agitate for an additional 2 hours. At the end of the reaction, the reaction mixture was poured into 300 mL of water which produced a precipitate. The precipitate was filtered off and washed with water.
This gave 11 g (94% of the theoretical) of tert.butyl (4-bromo-3-tert.butoxycarbonylaminophenyl)*carba mate.
1 H-NMVR (300 MHz, DMSO-D6): 65 9.51 11H); 8.43 1H); 7.89 1H); 7.47 1H); 7.18 1H); 1.47 18H).
B. Synthesis of tert-butvl r3-tert-butoxvcarbonlamino-4(4,4,5,5-tetramethvlri.3. 2ldioxa-2-borolanvl)Dhenvllcarbamate 210 mL of degassed dioxane was added under argon to. a mixture of 7.8. g (20.2 mmoles).of tert. butyl (4-bromo-3-tert.butoxycarbonylaminophenyl)carbamate from step A, 12.8 g (50.6 mmoles) of 5'-octamethyl2,2'lbi{[1,3,21dioxaborinanyl}, 2 g (2.9 mnmoles) of dichloro-I1,1'-bis(diphenylphosphino)ferrocene]palladium [PdCl 2 (dppf)] and 6.2 g (63.2 mmoles) of potassium acetate. The mixture was allowed to agitate 26 hours at 80 oC and to it was then added a mixture of 4.2 g (16.9 mmoles) of diboronpinacole ester and 700 mg (0.95 mmole) of PdCl2(dppf). The reaction mixture was then allowed to agitate for an additional 14 hours at 80 °C after which it was poured into water and extracted with ethyl acetate.
The organic phase was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered, and the filtrate was evaporated. The resulting crude product was purified on deactivated silica gel with hexane/ethyl acetate This gave 6.20 g (71% of the theoretical) of tert.butyl [3-tert.butoxycarbonylamino- 4 (4,4,5,5-tetramethyl[1,3,2]dioxa-2-borolanyl)phenyl]carbamate.
C. Synthesis of (1,1'-biphenvl)-2,4-diamines 0.09 g (0.0002 mole) of tert.butyl [3-tert.butoxycarbonylamino- 4 4 4 methyl-[1,3,2]dioxa-2-borolanyl)phenyl]carbamate from step B and 0.0004 mole of the appropriate bromo derivative were dissolved in 10 mL of 1,2-dimethoxyethane under argon. Then, 0.01 g (0.000005 mole) of tetrakis(triphenylphosphine)palladium and 0.26 mL of 2N potassium carbonate solution were added, and the reaction mixture was heated to 80 OC. At the end of the reaction, the reaction mixture was poured into 10 mL of ethyl acetate and the organic phase was extracted with dilute sodium hydroxide and dried with magnesium sulfate. The solvent was distilled off in a rotary evaporator, and the residue was purified on silica gel with petroleum ether/ethyl acetate The resulting product in 4 mL of ethanol was heated to OC. Then, to prepare the hydrochloride, 1.5 mL of a 2.9 molar ethanolic hydrochloric acid solution was added dropwise. The precipitate was filtered off, washed twice with 1-mL portions of ethanol and dried.
a. Biphenvl-2,4.4'-triamine hydrochloride Bromo derivative used: 4-bromoaniline Mass spectrum: MH 200 (100) b. 2',4'-Diaminobiphenyl-4-ol hydrochloride Bromo derivative used: 4-bromophenol Mass spectrum: MH' 201 C. 2',4'-Diaminobiphenvl-3-ol hydrochloride Bromo derivative used: 3-bromophenol Mass spectrum: MH' 201 d. Biohenvl-2,4-diamifle hydrochloridIe Bromo derivative used: 4-bromobenzene Mass spectrum: MH' 185 (100) e. 3'-Methoxybipheflyl-2,4-diamifle hydrochloride Bromo derivative used: 3-brornoanisole Mass spectrum: MH' 215 f. 4-Benizo f 1 .3 dioxol-5-vlbenzene-1, .3-d ia mine hydrochloride Bromo derivative used: 5-bromobenzo[ 1,3jdioxol Mass spectrum: MH' 229 g. 4'-Methvlbiiohenvl-2,4-diamifle hydrochloride Bromo derivative used: 4-bromotoluene Mass spectrum: MH' 199 (100) h. 4'-Fluorobiphenvi-2,4-diamifle hydrochloride Bromo derivative used: 4-fluoro-1-bromobenzefle Mass spectrum: MH' 23 (100) L. 2' .4'-Diaminobiohenl-4-carboflitrile hydrochloride Bromo derivative used: 4-bromobenzonitrile Mass spectrum: MH' 210 j. 1 ,4'-Diaminobirhefl-3-vl)ethalofe hydrochloride Bromo derivative used: 3-bromoacetophenone Mass spectrum: MH' 227 k. 4'-Nitrobiphenvl-2,4-diamifle hydrochloride Bromo derivative used: 4-bromonitrobeflzefe Mass spectrum: MH' 230 (100) 1. 2'-Nitrb el~-,-iame hydrochloride Bromo derivative used: 2-bromonitrobeflzefle Mass spectrum: MH' 230 (100) M. 4'-Trifluoromethylbipheflyl-2,4-dia ifle hydrochloride Bromo derivative used: 4-bromotrifluoromethylbelzefle Mass spectrum: MH' 253 n. 2',4'-Dimethylbioheflyl-2,4-diamifle hydrochloride Bromo derivative used: 2-bromo-m-xylene Mass spectrum: MH' 213 0. 4'-Chlorobiiheflyl-2,4-diamifle hydrochloride Bromo derivative used: 4-bromochlorobelzefle Mass spectrum: MH' 219 (28) p. 4'-Methvlsulfa nvlbi phenl-2,4-d iaminle hydrochloride Bromo derivative used: 1 -bromo-4-methylsulfaflylbelzefle Mass spectrum: MH' 231 (18) Examples 2 to 17: Hair Colorants Hair colorant solutions having the following composition were prepared: 1.25 mmoles 1.25 mmoles g g g 0.3 g to 100.0 g of coupler of formula as per Table 1 of developer according to Table 1 of potassium oleate aqueous solution) of ammonia (22% aqueous solution) of ethanol of ascorbic acid water Just before use, 50 g of the foregoing coloring solution was mixed with 50 g of a 6% aqueous hydrogen peroxide solution. The mixture was then applied to bleached hair.
After an exposure time of 30 min at 40 the hair was rinsed with water, washed with a commercial shampoo and dried. The resulting color shades are presented in Table 1.
17 TABLE 1 Developer Example No.
Coupler of formula
(I)
1.
1,4-Diaminobenzene
II.
2,5-Diaminotoluene sulfate
III.
2,5-Diaminophenylethanol sulfate per Ex.
per Ex.
per Ex.
per Ex.
per Ex.
per Ex.
per Ex.
per Ex.
per Ex.
per Ex.
per Ex.
per Ex.
dark dark dark dark dark dark dark dark dark dark dark dark blue blue blue blue blue blue blue blue blue blue blue blue dark dark dark blue dark dark dark dark blue blue blue blue blue blue blue blue blue blue blue dark blue dark blue dark blue dark blue dark blue dark blue blue blue blue blue blue blue
IV.
(2'-hydroxyethyl)pyrazole sulfate purple purple purple purple purple purple purple purple purple purple purple purple 14 As per Ex. 1 r dark blue blue blue purple TABLE 1 Continuation As per Ex. in As per Ex. lo As per Ex. 1p dark blue blue dark blue blue dark blue blue blue blue blue purple purple purple Examples 18 to 41 Hair Colorants Hair colorant solutions of the following composition were prepared: Xg Ug Yg Zg 10.0 g 10.0 g 10.0 g 0.3 g to 100.0 g of (1,1'-biphenyl)-2,4-diamine [coupler K1 to K4 of formula as per Table 4] of developer E8 to E15 as per Table 2 of coupler K11 to K36 as per Table 4 of direct dye D1 to D3 as per Table 3 of potassium oleate aqueous solution) of ammonia (22% aqueous solution) of ethanol of ascorbic acid water Just before use, 30 g of the foregoing coloring solution was mixed with 30 g of a 6% aqueous solution of hydrogen peroxide. The mixture was then applied to bleached hair. After an exposure time of 30 min at 40 OC, the hair was rinsed with water, washed with a commercial shampoo and dried. Table 5 shows the coloring results.
TABLE 2 Developers E8 1 ,4-diaminobenzene E9 2-(2,5-d iaminophenyl) ethanl sulfate 3-methyl-4-amiflophell Ell1 4-amino-2-aminomlethylPhelol dihydrochioride E12 4-aminophenol E13 N,N-bis(2'-hydroxyethyl)-p-pheflylefediamifle sulfate El14 4,5-diamino-1 -(2'-hydroxyethyl)pyrazole sulfate 2,5-diaminotoluene sulfate TABLE 3 Direct Dyes Dl 2,6-diamino-3-[(3-pyridilyl)azo]pyridifle D2 6-chloro-2-ethylamino-4-litropheloI D3 2-amino-6-chloro-4-nitrophell TABLE 4 Couplers Ki biphenyl-2,4,4'-triamifle hydrochloride K2 biphenyl-2,4-diamifle hydrochloride K3 2',4'-diaminobiphelyl-4-ol hydrochloride K4 2',4'-diaminobiphelyl-3-ol hydrochloride Ki 1 1 ,3-diaminobenzene Ki12 2-amino-4-(2'-hydroxyethyl)aminfoaflisole sulfate Ki13 1, ,3-dia mino-4-(2'-hyd roxyethoxy) benlzene sulfate K14 2,4-diamino-5-fluorotoluefle sulfate K1 5 3-amino-2-methylamilo-6-mlethoxypyridifle K16 3,5-diamino-2,6-dimethoxypyridifle dihydrochloride K1 7 2,4-diamino-5-ethoxytoluefle sulfate Ki18 N-(3-dimethylamino)phelylurea K1 9 1 ,3-bis(2,4-diaminophenoxy)propafle tetrahydrochloride K21 3-aminophenol TABLE 4 Continuation K22 5-amino-2-methylphenol K23 3-a mi no-2-chloro-6-methyl phenll K24 5-a mino-4-f luoro-2-methyl phenlol sulfate 1-naphthol K26 1 -acetoxy-2-methylnaphthalefle K3.1 1 ,3-dihydroxybenzene K32 2-methyl-i ,3-dihydroxybenzene K33 1 -chioro-2,4-dihydroxybenzefle K34 4-.(2'-hyd roxyethyl) amino- 1 ,2-methylenedioxybenzene .HCI 3,4-methylenedioxyphenol K36 21 T ABLE 5 Hair Colorants Example'No. 118 19 20 21 222 Dyes j(Dyes in grams) K1 ''1i 0,12 0,05 0,017 0,10 K3 0,05 10,1 1 0,10 Colrig rsuts blnd blnd blond blond blon Iblond 22 TABLE 5 Continuation Example No.
Dyes 24 125 126 '127 ]28 129 (Dyes in grams) K2 122L122 100 jo 00jo0 7 10,10 10,12- E8 E9 10,25 10,3 0,25 0 ,3 0,251 K12 0,05 K13 0,05 K31 0,20 0,15 0,20 0,10 K32 0,20 -,10 0,10 K33 0,20 K21 0,05 K22 0,05 K23 0,05 0,10 0,10 0,10 nd blond blond blond blond blond 23 TABLE 5 Continuation Example No. J30 31 ~32 ~33 134 135 Dyes j in grams) K 3 0,1i 10,12 10,05 10,07 10,10 10,12 E8 0,30 0 2 E9 02 0,25 0,3 0,25 K 12 0,05 K13 0,05 K 31 0,20 0,15 0,20 0,10 K32 0,20 0,10 0,10 K 33 0,20 K21 0,05 K22 0,05 K 23 0,05 0,10. 0,10 0,10 Coloring results blond blond blond blond Iblond Iblond 24 TABLE 5 Continuation
I
Examples 42 to 65 Hair Colorants Dye carriers in cream form and having the following composition were prepared: Xg Ug Yg Zg 15.0 0.3 of (1,1'-biphenyl)-2,4-diamine (coupler K1 to K4 of formula as per Table 4) of developer E8 to E15 as per Table 2 of coupler K11 to K36 as per Table 4 of direct dye D2 as per Table 3 of cetyl alcohol of ascorbic acid of sodium lauryl alcohol diethylene glycol ether sulfate, 28% aqueous solution of ammonia, 22% aqueous solution of sodium sulfite, anhydrous water g 0.3 g to 100.0 g Just before use, 30 g of the foregoing coloring cream was mixed with 30 g of a 6% aqueous solution of hydrogen peroxide. The mixture was then applied to the hair.
After an exposure time of 30 min at 40 the hair was rinsed with water, washed with a commercial shampoo and dried. The coloring results are presented in Table 6.
26 TABLE 6 Hair Colorants TAPI P P rnntin".qtinn Example No. 48 49 50 1 51 1 52 Dyes (Dyes in grams) E8 E13 1,6 0,7 1,8 0,7 0,7 K(12 0,6 K(31 1,10 1,10 1,10 0,40 0,40 0,.40 K(23 0,05 0,10 0,10 0,10 D2 0I. 10 0b10 0,10 Coloring resultsj black .l-black :black brown !brown Ibrown I A.
27 TABLE 6 Continuation Example No. 54 ~55 156 57 158 Dyes* (Dyes in grams) 3 1,15 0O,1 E8 E13 1,6 0,7 L1 ,8 0,7 0,7 K12 0,6 K31 1,10 1,10 1,10 0,40 0,40 0,40 K23 0,05 0,10 0,10 0,10 D2 1 000,10 10,10 Coloring resultsblc black black brown bon brw ]bak.bow irw TABLE 6 Continuation
Claims (9)
1. Agent for oxidative dyeing of keratin fibers based on a developer-coupler combination, characterized in that it contains as the coupler at least one biphenyl)-2,4-diamine derivative of formula or a physiologically tolerated derivative thereof R3 R2 R4 R1 HN NH 2 wherein R1, R2, R3, R4 and R5 can be equal or different and independently of each other denote hydrogen, a halogen atom, a cyano group, a hydroxyl group, a Cl-C 4 -alkoxy group, a C 1 -C 4 -hydroxyalkoxy group, a C 1 -C 6 -alkyl group, a C]-C 4 -alkyl thioether group, a mercapto group, a nitro group, an amino group (NH 2 a C 1 -C 4 -monoalkylamino group, a di(C 1 -C 4 )-alkylamino group, a trifluoromethyl group, a -C(O)H group, a -C(O)CH 3 group, a -C(O)CF 3 group, an -Si(CH 3 3 group, a Cl-C 4 -hydroxyalkyl group, a C 2 -C 4 -dihydroxyalkylgroup, a -CH= CHR6 group, a -(CH 2 p C0 2 R7 group or a -(CH 2 ),R8 group with p 1, 2, 3 or 4, a -C(R9)=NR10 group or a C(R12)H-NR13R14 group, or two adjacent R1 to R5 groups form an O-CH 2 -O bridge.; R6 denotes hydrogen, a nitro group, a CO 2 R7 group or a -C(O)CH 3 group; R7, R9 and R12 can be equal or different and independently of each other denote hydrogen or a C,-C 4 -alkyl group; R8 denotes an amino or nitrile group; R13 and R14 can be equal or different and independently of each other denote hydrogen, a hydroxyl group, a Cl-C 4 -alkyl group, a C 1 -C 4 -hydroxyalkyl group, a C 2 -C 4 dihydroxyalkyl group or a group of formula 29 R11 and R 1 denotes hydrogen, an amino group or a hydroxyl group.
2. Agent according to Claim 1, characterized in that' at least three of the R1 to groups denote hydrogen;
3. Agent according to Claim 1-or*2, characterized in that three of the R1 to groups denote hydrogen and the remaining two groups independently of each other denote hydrogen, a methoxy group, a hydroxyl group, a C,-C 4 -alkyl group, a C 1 -C 4 hydroxyalkyl group or an amino group, or when the two remaining groups are adjacent to each other they together form an -0-CH 2 bridge.
4. Agent according to one of Claims 1 to 3, characterized in that'the (1,1 '-biphenyl)- 2,4-diamine derivative of formula is selected from among biphenyl-2,4-diamine; 4- benzo[1,3]dioxol-5-ylbenzene-1,3-diamine; 4'-hydroxybiphenyl-2,4-diamine; 4'-ami- nobiphenyl-2,4-diamine; 3'-hydroxybiphenyl-2,4-diamine, 4'-methoxybiphenyl-2,4- diamine and the physiologically tolerated salts thereof.
Agent according to one of Claims 1 to 4, characterized in that it contains the (1,1'-biphenyl)-2,4-diamine of formula in an amount from 0.005 to 20 weight percent.
6. Agent according to one of Claims 1 to 5, characterized in that it has a pH from to 11.5.
7. Agent according to one of Claims 1 to 6, characterized in that the developer is selected from the group consisting of 1,4-diaminobenzene, 1,4-diamino-2- methylbenzene, 1,4-diamino-2,6-dimethylbenzene, 1,4-diamino-3,5-diethylbenzene, 1,4-diamino-2,5-dimethylbenzene, 1,4-diamino-2,3-dimethylbenzene, 2-chloro-1,4- diaminobenzene, 1,4-diamino-2-(thiophen-2-yl)benzene, 1,4-diamino-2-(thiophen-3- yl)benzene, 1,4-diamino-2-(pyridin-3-yl)benzene, 2,5-diaminobiphenyl; 1,4-diamino- 2-methoxymethylbenzene, 1,4-diamino-2-aminomethylbenzene, 1,4-diamino-2-hy- droxymethylbenzene, 1 ,4-diamino-2-(2-hydroxyethoxy)benzene, 2-[2-(acetylami- no)ethoxy]-1,4-diaminobenzene, 4-phenylaminoaniline, 4-dimethylaminoaniline, 4- diethylaminoaniline, 4-dipropylaminoaniline, 4-[ethyl-(2-hydroxyethyl)amino]aniline, 4-fd i(2-hyd roxyethyl) aminolalilifle, 4-[di(2-hYdroxyethyl)amifl-2-methylalilifle, 4-[(2-methoxyethyl)aminolaniline, 4-[(3-hydroxypropyl)aminolalhlifle, 4-[(2,3-dihy- droxypropyl)aminolaniline, 1 ,4-diamino-2-(2-hydroxyethyl) benlzene, 1 phenyl)ethanol, 1 ,4-d iamino-2- (1 -methylethyl) benzene, 1 ,3-bis-Ii(4-aminophenyl)(2- hydroxyethyl)aminol-2-propanol, 1 ,4-bis-t(4-aminophenyl)aminol butanle, 1 ,8-bis- 5-diaminophenoxy)-3,6-dioxaoctafle, 4-aminophenol, 4-amino-3-methyl phenol, 4- amino-3-(hyd roxymethyl) phenol, 4-amino-3-f luoro phenol, 4-methylaminophenol, 4- amino-2-(aminomethyl) phenlol, 4-amino-2-(hydroxymethyl)phelal, 4-amino-2-fluoro- phenol, 4-amino-2-[(2-hydroxyethyl)aminolmethylphenol, 4-amino- 2-methyl phenol, 4-amino-2-(methoxymethyl) phenol, 4-amino-2-(2-hyd roxyethyl) phenlol, acid, 2,5-diaminopyridine, 2,4,5,6-tetraaminopyrimidine, 2,5,6-triamino-4-(1 H)-pyri- midone, 4,5-diamino-1 -(2-hydroxyethyl)-1 H-pyrazole, 4, 5-diamino-l1-(1 -methylethyl)- 1 H-pyrazole, 4,5-diamino-1 -l(4-methylphenyl)methyl]-1 H-pyrazole, 1 -[(4-chlorophen- yl)methyll-4,5-diamino-1 H-pyrazole, 4,5-diamino-1 -methyl-i H-pyrazole, 4,5-diamino-3- methyl-i -methyl-i H-pyrazole, 4, 5-diamino-3-methyi-1 -methyl-i H-pyrazole [sic Translator], 2-aminophenol, 2-amino-6-methylphenol and 2-ami no-5-methyl phenol.
8. Agent according to one of Claims 1 to 7, characterized in that it contains each of the developers and couplers in a total amount of 0.005 to 20 based on the total amount of colorant.
9. Agent according to one of Claims 1 to 8, characterized in that it contains additionally at least one direct dye. Agent according to one of Claims 1 to 9, characterized in that it is a hair colorant. 0 31 O 11. (1,1'-Biphenyl)-2,4-diamine derivative of general formula (II) SR3 S. R2 R4 R1 H 2 N O NH NH wherein R1,R2,R3,R4,R5 can be equal or different and independently of each other denote hydrogen, hydrogen [sic Translator], a chlorine atom, a fluorine atom, a cyano group, a hydroxyl groupa Cl-C 4 -alkoxy group, a Cl-C 4 -hydroxyalkoxy group, a C,-C 6 -al- kyl group, a Cl-C 4 -alkyl thioether group, a mercapto group, a nitro group, an amino group (NH 2 a Cl-C 4 -monoalkylamino group, a di(C 1 -C 4 )-alkylamino group, a tri- fluoromethyl group, a -C(O)H.group, a -C(O)CH 3 group, a -C(O)CF 3 group, .an -Si(CH 3 3 group, a Cl-C 4 -hydroxyalkyl group, a C 2 -C 4 -dihydroxyalkyl group, a -CH=CHR6 group, a -(CH,)p-CO 2 R7 group, a -(CH 2 )p-R8 group with p 1,2,3 or 4, a -C(R9)=NR10 group or a C(R12)H-NR13R14 group, or two adjacent R1 to groups form an -O-CH 2 bridge; R6 denotes hydrogen, a nitro group, a CO 2 R7 group or a -C(O)CH 3 group; R7,R9 and R12 can be equal or different and independently of each other denote hydrogen or a Cl-C 4 -alkyl group; R8 denotes an amino group or a nitrile group; R13 and R14 can be equal or different and independently of each other denote hydrogen, a hydroxyl group, a Cl-C 4 -alkyl group, a Cl-C 4 -hydroxyalkyl group, a C2-C4- dihydroxyalkyl group or a group having the formula and R11 denotes hydrogen, an amino group or a hydroxyl group; and at least one of the R1 to R5 groups does not denote hydrogen: or. the physiologically tolerated salts thereof. DATED: 5 January 2006 PHILLIPS ORMONDE FITZPATRICK Attorneys for: P&G CLAIROL, INC.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10104770.3 | 2001-02-02 | ||
| AU2002210494A AU2002210494A1 (en) | 2001-02-02 | 2001-09-10 | Colouring agents for keratin fibres containing (1.1'-biphenyl)-2.4-diamine derivatives in addition to novel (1.1'-biphenyl)-2.4-diamine-derivatives |
| PCT/EP2001/010409 WO2002062307A1 (en) | 2001-02-02 | 2001-09-10 | Colouring agents for keratin fibres containing (1.1'-biphenyl)-2.4-diamine derivatives in addition to novel (1.1'-biphenyl)-2.4-diamine-derivatives |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2002210494A Division AU2002210494A1 (en) | 2001-02-02 | 2001-09-10 | Colouring agents for keratin fibres containing (1.1'-biphenyl)-2.4-diamine derivatives in addition to novel (1.1'-biphenyl)-2.4-diamine-derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2006200042A1 true AU2006200042A1 (en) | 2006-02-02 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006200042A Abandoned AU2006200042A1 (en) | 2001-02-02 | 2006-01-06 | Dyeing agents for keratin fibers, containing (1,1'-biphenyl)-2,4-diamine derivatives, and new (1,1'-biphenyl)-2,4-diamine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| AU (1) | AU2006200042A1 (en) |
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2006
- 2006-01-06 AU AU2006200042A patent/AU2006200042A1/en not_active Abandoned
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