CN1551875A - 间氨基苯酚衍生物及包含这些化合物的染料 - Google Patents
间氨基苯酚衍生物及包含这些化合物的染料 Download PDFInfo
- Publication number
- CN1551875A CN1551875A CNA028161270A CN02816127A CN1551875A CN 1551875 A CN1551875 A CN 1551875A CN A028161270 A CNA028161270 A CN A028161270A CN 02816127 A CN02816127 A CN 02816127A CN 1551875 A CN1551875 A CN 1551875A
- Authority
- CN
- China
- Prior art keywords
- amino
- phenol
- thienyl
- diamino
- benzene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical class NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 239000003086 colorant Substances 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 64
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 39
- 229940018563 3-aminophenol Drugs 0.000 claims description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 24
- -1 N-R1 Chemical compound 0.000 claims description 22
- 239000003153 chemical reaction reagent Substances 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 21
- 230000000855 fungicidal effect Effects 0.000 claims description 20
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 16
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 16
- 238000004043 dyeing Methods 0.000 claims description 15
- 239000000118 hair dye Substances 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 239000005864 Sulphur Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 5
- DFLOUCCXIYBOBE-UHFFFAOYSA-N 5-amino-2-(2-chlorothiophen-3-yl)phenol Chemical compound OC1=CC(N)=CC=C1C1=C(Cl)SC=C1 DFLOUCCXIYBOBE-UHFFFAOYSA-N 0.000 claims description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- HHVMYUPMJJDVPG-UHFFFAOYSA-N 1-(2,5-diaminophenyl)ethanol Chemical compound CC(O)C1=CC(N)=CC=C1N HHVMYUPMJJDVPG-UHFFFAOYSA-N 0.000 claims description 4
- 150000004782 1-naphthols Chemical class 0.000 claims description 4
- HCPJEHJGFKWRFM-UHFFFAOYSA-N 2-amino-5-methylphenol Chemical compound CC1=CC=C(N)C(O)=C1 HCPJEHJGFKWRFM-UHFFFAOYSA-N 0.000 claims description 4
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 claims description 4
- GHNSMDAVVQUQIA-UHFFFAOYSA-N 5-amino-2-(5-chlorothiophen-2-yl)phenol Chemical compound OC1=CC(N)=CC=C1C1=CC=C(Cl)S1 GHNSMDAVVQUQIA-UHFFFAOYSA-N 0.000 claims description 4
- GDMWNXWNAFZOTH-UHFFFAOYSA-N 5-amino-2-thiophen-3-ylphenol Chemical group OC1=CC(N)=CC=C1C1=CSC=C1 GDMWNXWNAFZOTH-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 claims description 4
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical class C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 3
- 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
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 claims description 3
- XYRDGCCCBJITBH-UHFFFAOYSA-N 3-amino-2-chloro-6-methylphenol Chemical compound CC1=CC=C(N)C(Cl)=C1O XYRDGCCCBJITBH-UHFFFAOYSA-N 0.000 claims description 3
- YYFURQPOHJETNS-UHFFFAOYSA-N 5-amino-2-(3-chlorothiophen-2-yl)phenol Chemical compound OC1=CC(N)=CC=C1C1=C(Cl)C=CS1 YYFURQPOHJETNS-UHFFFAOYSA-N 0.000 claims description 3
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 claims description 3
- HEAQOCBITATQEW-UHFFFAOYSA-N 5-amino-4-fluoro-2-methylphenol Chemical compound CC1=CC(F)=C(N)C=C1O HEAQOCBITATQEW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000001294 propane Substances 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- NKNCGBHPGCHYCQ-UHFFFAOYSA-N (2,5-diaminophenyl)methanol Chemical compound NC1=CC=C(N)C(CO)=C1 NKNCGBHPGCHYCQ-UHFFFAOYSA-N 0.000 claims description 2
- UQPKIBHPQJMLMI-UHFFFAOYSA-N (4-phenylphenyl)hydrazine Chemical compound C1=CC(NN)=CC=C1C1=CC=CC=C1 UQPKIBHPQJMLMI-UHFFFAOYSA-N 0.000 claims description 2
- XAMFKUIHKWABQW-UHFFFAOYSA-N 1-[2-(4-amino-2-hydroxyphenyl)thiophen-3-yl]ethanone Chemical compound C1=CSC(C=2C(=CC(N)=CC=2)O)=C1C(=O)C XAMFKUIHKWABQW-UHFFFAOYSA-N 0.000 claims description 2
- ADSDGUMAULLZIK-UHFFFAOYSA-N 1-[3-(4-amino-2-hydroxyphenyl)thiophen-2-yl]ethanone Chemical compound S1C=CC(C=2C(=CC(N)=CC=2)O)=C1C(=O)C ADSDGUMAULLZIK-UHFFFAOYSA-N 0.000 claims description 2
- BOIHHBKIJHXIBV-UHFFFAOYSA-N 1-[4-(4-amino-2-hydroxyphenyl)thiophen-2-yl]ethanone Chemical compound S1C(C(=O)C)=CC(C=2C(=CC(N)=CC=2)O)=C1 BOIHHBKIJHXIBV-UHFFFAOYSA-N 0.000 claims description 2
- KMQBSXBRDGYOQZ-UHFFFAOYSA-N 1-[4-(4-amino-2-hydroxyphenyl)thiophen-3-yl]ethanone Chemical compound CC(=O)C1=CSC=C1C1=CC=C(N)C=C1O KMQBSXBRDGYOQZ-UHFFFAOYSA-N 0.000 claims description 2
- WWWOKPYOFBBSQS-UHFFFAOYSA-N 1-[5-(4-amino-2-hydroxyphenyl)thiophen-2-yl]ethanone Chemical compound S1C(C(=O)C)=CC=C1C1=CC=C(N)C=C1O WWWOKPYOFBBSQS-UHFFFAOYSA-N 0.000 claims description 2
- RENHFYNCXOQYQA-UHFFFAOYSA-N 1-[5-(4-amino-2-hydroxyphenyl)thiophen-3-yl]ethanone Chemical compound CC(=O)C1=CSC(C=2C(=CC(N)=CC=2)O)=C1 RENHFYNCXOQYQA-UHFFFAOYSA-N 0.000 claims description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical class CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims description 2
- SYEYEGBZVSWYPK-UHFFFAOYSA-N 2,5,6-triamino-4-hydroxypyrimidine Chemical compound NC1=NC(N)=C(N)C(O)=N1 SYEYEGBZVSWYPK-UHFFFAOYSA-N 0.000 claims description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-Lutidine Substances CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 2
- BQHMISUMCDYQTR-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylamino)ethanol Chemical compound OCCNC1=CC=C2OCOC2=C1 BQHMISUMCDYQTR-UHFFFAOYSA-N 0.000 claims description 2
- KWSVXCAQFTWTEF-UHFFFAOYSA-N 2-(2,5-diaminophenyl)ethanol Chemical compound NC1=CC=C(N)C(CCO)=C1 KWSVXCAQFTWTEF-UHFFFAOYSA-N 0.000 claims description 2
- ZTNLMELMADJSAH-UHFFFAOYSA-N 2-(3-aminoanilino)ethanol Chemical compound NC1=CC=CC(NCCO)=C1 ZTNLMELMADJSAH-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- XNIOWJUQPMKCIJ-UHFFFAOYSA-N 2-(benzylamino)ethanol Chemical class OCCNCC1=CC=CC=C1 XNIOWJUQPMKCIJ-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
- BMTSZVZQNMNPCT-UHFFFAOYSA-N 2-aminopyridin-3-ol Chemical compound NC1=NC=CC=C1O BMTSZVZQNMNPCT-UHFFFAOYSA-N 0.000 claims description 2
- WNYJRJRHKRZXEO-UHFFFAOYSA-N 2-propan-2-ylbenzene-1,4-diamine Chemical compound CC(C)C1=CC(N)=CC=C1N WNYJRJRHKRZXEO-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- YBJRIYRYCGKUIM-UHFFFAOYSA-N 3-(2-hydroxyethylamino)phenol Chemical compound OCCNC1=CC=CC(O)=C1 YBJRIYRYCGKUIM-UHFFFAOYSA-N 0.000 claims description 2
- MZQGZBUNWFAKAC-UHFFFAOYSA-N 3-(4-aminoanilino)propan-1-ol Chemical compound NC1=CC=C(NCCCO)C=C1 MZQGZBUNWFAKAC-UHFFFAOYSA-N 0.000 claims description 2
- WAVOOWVINKGEHS-UHFFFAOYSA-N 3-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=CC(O)=C1 WAVOOWVINKGEHS-UHFFFAOYSA-N 0.000 claims description 2
- MESJRHHDBDCQTH-UHFFFAOYSA-N 3-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC(O)=C1 MESJRHHDBDCQTH-UHFFFAOYSA-N 0.000 claims description 2
- FLROJJGKUKLCAE-UHFFFAOYSA-N 3-amino-2-methylphenol Chemical compound CC1=C(N)C=CC=C1O FLROJJGKUKLCAE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
- IISRVEXNCGUXQJ-UHFFFAOYSA-N 3-methylbenzene-1,2,4-triamine Chemical compound CC1=C(N)C=CC(N)=C1N IISRVEXNCGUXQJ-UHFFFAOYSA-N 0.000 claims description 2
- LRZCBJYTBUZEFK-UHFFFAOYSA-N 3-n-(2-aminoethyl)benzene-1,3-diamine Chemical compound NCCNC1=CC=CC(N)=C1 LRZCBJYTBUZEFK-UHFFFAOYSA-N 0.000 claims description 2
- ZNBTUAAPXSCFBS-UHFFFAOYSA-N 4-(2-methoxyethoxy)benzene-1,3-diamine Chemical compound COCCOC1=CC=C(N)C=C1N ZNBTUAAPXSCFBS-UHFFFAOYSA-N 0.000 claims description 2
- NZMFZUGEOCZRAX-UHFFFAOYSA-N 4-amino-2-(2-hydroxyethyl)phenol Chemical compound NC1=CC=C(O)C(CCO)=C1 NZMFZUGEOCZRAX-UHFFFAOYSA-N 0.000 claims description 2
- WHLALWVCKSOVKK-UHFFFAOYSA-N 4-amino-2-(2-hydroxyethylamino)-3-methylphenol Chemical compound CC1=C(N)C=CC(O)=C1NCCO WHLALWVCKSOVKK-UHFFFAOYSA-N 0.000 claims description 2
- PZKNKZNLQYKXFV-UHFFFAOYSA-N 4-amino-2-(aminomethyl)phenol Chemical compound NCC1=CC(N)=CC=C1O PZKNKZNLQYKXFV-UHFFFAOYSA-N 0.000 claims description 2
- WSEFOZIMAJPJHW-UHFFFAOYSA-N 4-amino-2-(hydroxymethyl)phenol Chemical compound NC1=CC=C(O)C(CO)=C1 WSEFOZIMAJPJHW-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
- DHKIYDNMIXSKQP-UHFFFAOYSA-N 4-amino-3-(hydroxymethyl)phenol Chemical compound NC1=CC=C(O)C=C1CO DHKIYDNMIXSKQP-UHFFFAOYSA-N 0.000 claims description 2
- MNPLTKHJEAFOCA-UHFFFAOYSA-N 4-amino-3-fluorophenol Chemical compound NC1=CC=C(O)C=C1F MNPLTKHJEAFOCA-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
- XCJRRZLPXALCIP-UHFFFAOYSA-N 4-n-(2-methoxyethyl)benzene-1,4-diamine Chemical compound COCCNC1=CC=C(N)C=C1 XCJRRZLPXALCIP-UHFFFAOYSA-N 0.000 claims description 2
- PPPNUSFRWJVHQB-UHFFFAOYSA-N 4-n-butylbenzene-1,4-diamine Chemical compound CCCCNC1=CC=C(N)C=C1 PPPNUSFRWJVHQB-UHFFFAOYSA-N 0.000 claims description 2
- BDAMXFTYZBIBHB-UHFFFAOYSA-N 5-amino-2-(2-aminothiophen-3-yl)phenol Chemical compound S1C=CC(C=2C(=CC(N)=CC=2)O)=C1N BDAMXFTYZBIBHB-UHFFFAOYSA-N 0.000 claims description 2
- CNEHJJGZSQRWRR-UHFFFAOYSA-N 5-amino-2-(2-hydroxyethoxy)phenol Chemical compound NC1=CC=C(OCCO)C(O)=C1 CNEHJJGZSQRWRR-UHFFFAOYSA-N 0.000 claims description 2
- WQXNQTVZPSEQQC-UHFFFAOYSA-N 5-amino-2-(2-methylthiophen-3-yl)phenol Chemical compound S1C=CC(C=2C(=CC(N)=CC=2)O)=C1C WQXNQTVZPSEQQC-UHFFFAOYSA-N 0.000 claims description 2
- KBRXMBIPMWXADS-UHFFFAOYSA-N 5-amino-2-(2-nitrothiophen-3-yl)phenol Chemical compound OC1=CC(N)=CC=C1C1=C([N+]([O-])=O)SC=C1 KBRXMBIPMWXADS-UHFFFAOYSA-N 0.000 claims description 2
- IHWBWTVTAIWKFF-UHFFFAOYSA-N 5-amino-2-(3-aminothiophen-2-yl)phenol Chemical compound C1=CSC(C=2C(=CC(N)=CC=2)O)=C1N IHWBWTVTAIWKFF-UHFFFAOYSA-N 0.000 claims description 2
- VNIIHKLHTHSOHS-UHFFFAOYSA-N 5-amino-2-(3-methylthiophen-2-yl)phenol Chemical compound C1=CSC(C=2C(=CC(N)=CC=2)O)=C1C VNIIHKLHTHSOHS-UHFFFAOYSA-N 0.000 claims description 2
- SRFPEVSSKIWESZ-UHFFFAOYSA-N 5-amino-2-(3-nitrothiophen-2-yl)phenol Chemical compound OC1=CC(N)=CC=C1C1=C([N+]([O-])=O)C=CS1 SRFPEVSSKIWESZ-UHFFFAOYSA-N 0.000 claims description 2
- JEZHAGPECRQRQR-UHFFFAOYSA-N 5-amino-2-(4-aminothiophen-2-yl)phenol Chemical compound NC1=CSC(C=2C(=CC(N)=CC=2)O)=C1 JEZHAGPECRQRQR-UHFFFAOYSA-N 0.000 claims description 2
- LSFCWPZNTPRNBG-UHFFFAOYSA-N 5-amino-2-(4-aminothiophen-3-yl)phenol Chemical compound NC1=CSC=C1C1=CC=C(N)C=C1O LSFCWPZNTPRNBG-UHFFFAOYSA-N 0.000 claims description 2
- OTZLOVMQKMIVFX-UHFFFAOYSA-N 5-amino-2-(4-chlorothiophen-2-yl)phenol Chemical compound OC1=CC(N)=CC=C1C1=CC(Cl)=CS1 OTZLOVMQKMIVFX-UHFFFAOYSA-N 0.000 claims description 2
- MYZJUMQHAKSTSK-UHFFFAOYSA-N 5-amino-2-(4-chlorothiophen-3-yl)phenol Chemical compound OC1=CC(N)=CC=C1C1=CSC=C1Cl MYZJUMQHAKSTSK-UHFFFAOYSA-N 0.000 claims description 2
- DXHOOJOJJXZMLJ-UHFFFAOYSA-N 5-amino-2-(4-methylthiophen-2-yl)phenol Chemical compound CC1=CSC(C=2C(=CC(N)=CC=2)O)=C1 DXHOOJOJJXZMLJ-UHFFFAOYSA-N 0.000 claims description 2
- YXRDJHSJQSAENR-UHFFFAOYSA-N 5-amino-2-(4-nitrothiophen-2-yl)phenol Chemical compound OC1=CC(N)=CC=C1C1=CC([N+]([O-])=O)=CS1 YXRDJHSJQSAENR-UHFFFAOYSA-N 0.000 claims description 2
- XOXZFVRHGOFEQR-UHFFFAOYSA-N 5-amino-2-(4-nitrothiophen-3-yl)phenol Chemical compound OC1=CC(N)=CC=C1C1=CSC=C1[N+]([O-])=O XOXZFVRHGOFEQR-UHFFFAOYSA-N 0.000 claims description 2
- GTBRIKCCYRNCDJ-UHFFFAOYSA-N 5-amino-2-(5-aminothiophen-2-yl)phenol Chemical compound S1C(N)=CC=C1C1=CC=C(N)C=C1O GTBRIKCCYRNCDJ-UHFFFAOYSA-N 0.000 claims description 2
- BEYKZHJWNKAVLF-UHFFFAOYSA-N 5-amino-2-(5-aminothiophen-3-yl)phenol Chemical compound S1C(N)=CC(C=2C(=CC(N)=CC=2)O)=C1 BEYKZHJWNKAVLF-UHFFFAOYSA-N 0.000 claims description 2
- WKVNXPXUYNTUHK-UHFFFAOYSA-N 5-amino-2-(5-methylthiophen-2-yl)phenol Chemical compound S1C(C)=CC=C1C1=CC=C(N)C=C1O WKVNXPXUYNTUHK-UHFFFAOYSA-N 0.000 claims description 2
- UFHQSVQBDDOSCM-UHFFFAOYSA-N 5-amino-2-(5-methylthiophen-3-yl)phenol Chemical compound S1C(C)=CC(C=2C(=CC(N)=CC=2)O)=C1 UFHQSVQBDDOSCM-UHFFFAOYSA-N 0.000 claims description 2
- QFIBNYWDDMPJSP-UHFFFAOYSA-N 5-amino-2-(5-nitrothiophen-2-yl)phenol Chemical compound OC1=CC(N)=CC=C1C1=CC=C([N+]([O-])=O)S1 QFIBNYWDDMPJSP-UHFFFAOYSA-N 0.000 claims description 2
- SDHPRUCSSPSIPP-UHFFFAOYSA-N 5-amino-2-(5-nitrothiophen-3-yl)phenol Chemical compound OC1=CC(N)=CC=C1C1=CSC([N+]([O-])=O)=C1 SDHPRUCSSPSIPP-UHFFFAOYSA-N 0.000 claims description 2
- WMJYVKIFKBTVPL-UHFFFAOYSA-N 5-amino-2-(furan-2-yl)phenol Chemical compound OC1=CC(N)=CC=C1C1=CC=CO1 WMJYVKIFKBTVPL-UHFFFAOYSA-N 0.000 claims description 2
- GIAAVVJKVIITIY-UHFFFAOYSA-N 5-amino-2-(furan-3-yl)phenol Chemical compound OC1=CC(N)=CC=C1C1=COC=C1 GIAAVVJKVIITIY-UHFFFAOYSA-N 0.000 claims description 2
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- TWLMSPNQBKSXOP-UHFFFAOYSA-N 6358-09-4 Chemical compound NC1=CC([N+]([O-])=O)=CC(Cl)=C1O TWLMSPNQBKSXOP-UHFFFAOYSA-N 0.000 description 1
- PJLGLJUZECZTLB-UHFFFAOYSA-N B(O)(O)O.NC=1C=C(C=CC1)O Chemical class B(O)(O)O.NC=1C=C(C=CC1)O PJLGLJUZECZTLB-UHFFFAOYSA-N 0.000 description 1
- AOPIOSMLQFZIPA-UHFFFAOYSA-N CC1=C(C(=CC(=C1N)O)N)CCO Chemical compound CC1=C(C(=CC(=C1N)O)N)CCO AOPIOSMLQFZIPA-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-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
- LNMHTNHCPDMGOP-UHFFFAOYSA-N Cl.Cl.NC1=C(C(=C(C=C1)O)N)C Chemical compound Cl.Cl.NC1=C(C(=C(C=C1)O)N)C LNMHTNHCPDMGOP-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 229910003867 O—B—O Inorganic materials 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 244000225942 Viola tricolor Species 0.000 description 1
- 235000004031 Viola x wittrockiana Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 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
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- WRPSKOREVDHZHP-UHFFFAOYSA-N benzene-1,4-diamine Chemical compound NC1=CC=C(N)C=C1.NC1=CC=C(N)C=C1 WRPSKOREVDHZHP-UHFFFAOYSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- 150000002632 lipids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 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
- 239000007800 oxidant agent Substances 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 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
- CTYRPMDGLDAWRQ-UHFFFAOYSA-N phenyl hydrogen sulfate Chemical compound OS(=O)(=O)OC1=CC=CC=C1 CTYRPMDGLDAWRQ-UHFFFAOYSA-N 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- CDHUJLBZOFEXMY-UHFFFAOYSA-N phenylurea urea Chemical compound NC(=O)N.C1(=CC=CC=C1)NC(=O)N CDHUJLBZOFEXMY-UHFFFAOYSA-N 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-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
- 239000000376 reactant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 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
- 229960004418 trolamine Drugs 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
Abstract
本发明涉及由式(I)表示的3-氨基苯酚衍生物,其中R是由式(Ia)表示的芳族杂五元环化合物;或涉及其生理上可接受的水溶性盐。本发明还涉及基于显色剂-偶合剂组合的着色剂,所述着色剂的特征在于它们包含所述化合物。
Description
本发明涉及在6号位被取代的新型3-氨基苯酚衍生物和包含该化合物的试剂,所述试剂用于给角蛋白纤维染色,尤其是给人的毛发染色。
在角蛋白纤维染色领域中,尤其是在毛发染色领域中,氧化染料具有非常重要的作用。在这种情况下,当有适当氧化剂存在时,通过让某些显色剂与偶合剂反应产生染色效果。适合的显色剂尤其包括2,5-二氨基甲苯、2,5-二氨基苯基乙基醇、对氨基苯酚、1,4-二氨基苯和4,5-二氨基-1-(2-羟基乙基)吡唑,而适合的偶合剂包括例如间苯二酚、2-甲基间苯二酚、1-萘酚、3-氨基苯酚、间-苯二胺、苯二胺2-氨基-4-(2'-羟基乙基)氨基苯甲醚、1,3-氨基-4-(2'-羟基乙氧基)苯和2,4-二氨基-5-氟代甲苯。
用于给人的毛发染色的氧化染料除了能够产生期望强度的染色效果外,还必须满足其它许多要求。例如,这些染料从毒物学和皮肤病学角度上讲必须无害,且所获得的染发效果必须有良好的光不褪色性、抗烫发性、酸不褪色性和摩擦不褪色性。然而,在任何情况下,在不暴露于光、摩擦和化学物质的情况下,这些染色效果必须在至少4至6周的时间内保持稳定。此外,通过将合适的显色剂与偶合剂结合,所述染料必须能够产生大范围的不同色彩明暗效果。
尽管已知有许多偶合剂,但是目前还没有找到在各方面都确定能满足要求的染料。因此,仍需要能在尤其高的程度上满足上述要求的新型偶合剂。
现已发现,具有通式(I)的某些3-氨基苯酚衍生物尤其高度满足对于偶合剂的要求,并具有不褪色性,尤其在用最有名的显色剂洗涤时具有光不褪色性和色调(nuance)的耐受性。
因此,本发明的目的为式(I)的3-氨基苯酚衍生物或其生理上相容的水溶性盐,
其中R为式(Ia)的芳族杂五元环;X1、X2、X3和X4彼此独立地为硫、氮、N-R1、氧、C-R2、C-R3、C-R4或C-R5,条件为基团X1至X4中至少一种或最多三种为氮、N-R1、硫或氧,且如果有多个杂原子,基团X1至X4中不超过一种为硫、N-R1或氧;
R1为氢、C1-C6烷基、苯基、(C2-C4)-羟基烷基或乙酰基;
R2、R3、R4和R5彼此独立地表示氢、卤素原子(F、Cl、Br、I)、氰基、C1-C6烷基、C1-C4烷氧基、C1-C4烷基硫醚基、巯基、硝基、氨基、C1-C4烷氨基、二(C1-C4)烷氨基、羟基(C2-C4)烷氨基、二(羟基(C2-C4)烷基)氨基、(二羟基(C3-C4)烷基)氨基、三氟甲烷基、-C(O)CH3、C(O)CF3、-C(O)C、-Si(CH3)3、(C1-C4)羟基烷基或(C2-C4)二羟基烷基。
例如,式(I)的化合物可以是:
5-氨基-2-(3-噻吩基)苯酚、5-氨基-2-(3-呋喃基)苯酚、5-氨基-2-(吡咯-3-基)苯酚、5-氨基-2-(1-甲基-1H-吡咯-3-基)苯酚、5-氨基-2-(1,3-噻唑-2-基)苯酚、5-氨基-2-(1,3-噻唑-5-基)苯酚、5-氨基-2-(2-噻吩基)苯酚、5-氨基-2-(2-呋喃基)苯酚、5-氨基-2-(吡咯-2-基)苯酚、5-氨基-2-(1-甲基-1H-吡咯-2-基)苯酚、5-氨基-2-(2-氯-3-噻吩基)-苯酚、5-氨基-2-(2-甲基-3-噻吩基)苯酚、5-氨基-2-(2-硝基-3-噻吩基)苯酚、5-氨基-2-(2-氨基-3-噻吩基)苯酚、5-氨基-2-(2-乙酰基-3-噻吩基)苯酚、5-氨基-2-(2-甲酰基-3-噻吩基)苯酚、5-氨基-2-(4-氯-3-噻吩基)苯酚、5-氨基-2-(4-甲酰基-3-噻吩基)苯酚、5-氨基-2-(4-硝基-3-噻吩基)苯酚、5-氨基-2-(4-氨基-3-噻吩基)苯酚、5-氨基-2-(4-乙酰基-3-噻吩基)苯酚、5-氨基-2-(4-甲酰基-3-噻吩基)苯酚、5-氨基-2-(5-氯-3-噻吩基)苯酚、5-氨基-2-(5-甲基-3-噻吩基)苯酚、5-氨基-2-(5-硝基-3-噻吩基)苯酚、5-氨基-2-(5-乙酰基-3-噻吩基)苯酚、5-氨基-2-(5-氨基-3-噻吩基)苯酚、5-氨基-2-(5-甲酰基-3-噻吩基)苯酚、5-氨基-2-(5-甲酰基-3-呋喃基)苯酚、5-氨基-2-(3-氯-2-噻吩基)苯酚、5-氨基-2-(3-甲基-2-噻吩基)苯酚、5-氨基-2-(3-氯-2-噻吩基)苯酚、5-氨基-2-(3-氨基-2-噻吩基)苯酚、5-氨基-2-(3-乙酰基-2-噻吩基)苯酚、5-氨基-2-(3-甲酰基-2-噻吩基)苯酚、5-氨基-2-(3-硝基-2-噻吩基)苯酚、5-氨基-2-(4-氯-2-噻吩基)苯酚、5-氨基-2-(4-甲基-2-噻吩基)苯酚、5-氨基-2-(4-硝基-2-噻吩基)苯酚、5-氨基-2-(4-氨基-2-噻吩基)苯酚、5-氨基-2-(4-乙酰基-2-噻吩基)苯酚、5-氨基-2-(4-甲酰基-2-噻吩基)苯酚、5-氨基-2-(5-氯-2-噻吩基)苯酚、5-氨基-2-(5-甲基-2-噻吩基)苯酚、5-氨基-2-(5-硝基-2-噻吩基)苯酚、5-氨基-2-(5-氨基-2-噻吩基)苯酚、5-氨基-2-(5-乙酰基-2-噻吩基)苯酚、5-氨基-2-(5-甲酰基-2-噻吩基)苯酚、5-氨基-2-(5-甲酰基-2-呋喃基)苯酚、5-氨基-2-(5-硝基-1,3-噻唑-2-基)苯酚、5-氨基-2-(5-氨基-1,3-噻唑-2-基)苯酚、5-氨基-2-(2-硝基-1,3-噻唑-5-基)苯酚、5-氨基-2-(2-氨基-1,3-噻唑-5-基)苯酚、5-氨基-2-(3,5-甲基-1H-吡唑-4-基)苯酚和5-氨基-2-(5-硝基-4H-1,2,4-三唑-3-基)苯酚,及其生理上相容的水溶性盐。
优选符合下列条件的式(I)的化合物,其中:
(i)X2为硫,而X1、X3和X4为C-R2、C-R4和C-R5;或(ii)X1为硫,且X2、X3和X4为C-R3、C-R4和C-R5。
尤其优选下式(I)的化合物:
5-氨基-2-(3-噻吩基)苯酚、5-氨基-2-(2-氯-3-噻吩基)苯酚和5-氨基-2-(5-氯-2-噻吩基)苯酚及其生理上相容的水溶性盐。
式(I)的化合物可用作游离碱,以及用作与无机或有机酸,例如盐酸、硫酸、磷酸、乙酸、丙酸、乳酸或柠檬酸所形成的在生理上相容的盐的形式。
本发明的式(I)的氨基苯酚衍生物可通过例如类似于文献所述的合成方法来制备。
a)用四(三苯基膦)钯(O)催化偶合具有式(IIIa)的卤素取代芳族化合物的式(IIa)的适合的取代3-氨基苯酚硼酸衍生物,随后分离该偶合反应所需的保护性基团;
或
b)用四(三苯基膦)钯(O)催化偶合具有式(IIIb)的硼酸衍生物的式(IIb)的卤素-取代的3-氨基苯酚,随后分离该偶合反应所需的保护性基团:
式(IIa)、(IIb)、(IIIa)和(IIIb)的基团的含义如下:
Ra表示保护性基团,如在Organic Synthesis,第3章,Wiley Interscience,1991中的“Protective Groups”部分所述;
Rb和Rc分别独立地表示保护性基团,如在Organic Synthesis,第7章,Wiley Interscience,1991中的“Protective Groups”所述、或表示氢;
Rd为氢,或者两个Rd基团和O-B-O基团形成未取代的或取代的五链或六链脂环;
Hal为F、Cl、Br或J;和
X1、X2、X3和X4具有在式(I)中所给的含义。
式(I)的3-氨基苯酚衍生物为水溶性,并具有高颜色强度和优良的颜色稳定性的染色效果,尤其具有光不褪色性、洗涤不褪色性和摩擦不褪色性。而且,它们具有优良的贮存稳定性,尤其可用作下述的氧化着色剂的组分。
因此,本发明的另一目的是用于给角蛋白纤维染色的试剂,例如羊毛、毛皮、羽毛或毛发,尤其是人的毛发,所述试剂基于显色剂-偶合剂的组合,其特征在于它包含式(I)的至少一种3-氨基苯酚衍生物或其生理上相容的水溶性盐。
式(I)的3-氨基苯酚衍生物在本发明的着色剂中的含量按重量计为约0.005%至20%、约0.01%至5%、尤其优选为0.1%至2.5%。
所考虑的优选显色剂有例如1,4-二氨基苯(对-苯二胺)、1,4-二氨基-2-甲基苯(对-甲苯二胺)、1,4-二氨基-2,6-二甲基苯、1,4-二氨基-3,5-二乙基苯、1,4-二氨基-2,5-二甲基苯、1,4-二氨基-2,3-二甲基苯、2-氯-1,4-二氨基苯、1,4-二氨基-2-(噻吩-2-基)苯、1,4-二氨基-2-(噻吩-3-基)苯、1,4-二氨基-2-(吡啶-3-基)苯、2,5-二氨基联苯、1,4-二氨基-2-甲氧基甲基苯、1,4-二氨基-2-氨基甲基苯、1,4-二氨基-2-羟基甲基苯、1,4-二氨基-2-(2-羟基乙氧基)苯、2-(2-(乙酰氨基)乙氧基)-1,4-二氨基苯、4-苯基氨基苯胺、4-二甲基氨基苯胺、4-二乙基氨基苯胺、4-二丙基氨基苯胺、4-[乙基(2-羟基乙基)-氨基]-苯胺、4-[二(2-羟基乙基)氨基]苯胺、4-[二(2-羟基乙基)氨基]-2-甲基苯胺、4-[(2-甲氧基乙基)氨基]苯胺、4-[(3-羟丙基)氨基]苯胺、4-[(2,3-二羟基丙基)氨基]苯胺、1,4-二氨基-2-(1-羟基乙基)苯、1,4-二氨基-2-(2-羟基乙基)苯、1,4-二氨基-2-(1-甲基乙基)苯、1,3-双[(4-氨基苯基)(2-羟基乙基)氨基]-2-丙醇、1,4-双[(4-氨基苯基)氨基]丁烷、1,8-双(2,5-二氨基苯氧基)-3,6-二氧杂辛烷、4-氨基苯酚、4-氨基-3-甲基苯酚、4-氨基-3-(羟甲基)苯酚、4-氨基-3-氟苯酚、4-甲基氨基苯酚、4-氨基-2-(氨基甲基)苯酚、4-氨基-2-(羟甲基)苯酚、4-氨基-2-氟苯酚、4-氨基-2-[(2-羟基乙基)氨基]甲基苯酚、4-氨基-2-甲基苯酚、4-氨基-2-(甲氧基甲基)苯酚、4-氨基-2-(2-羟基乙基)苯酚、5-氨基水杨酸、2,5-二氨基吡啶、2,4,5,6-四氨基嘧啶、2,5,6-三氨基-4-(1H)-嘧啶酮、4,5-二氨基-1-(2-羟基乙基)-1H-吡唑、4,5-二氨基-1-(1-甲基乙基)-1H-吡唑、4,5-二氨基-1-[(4-甲基苯基)甲基]-1H-吡唑、1-[(4-氯代苯基)甲基]-4,5-二氨基-1H-吡唑、4,5-二氨基-1-甲基-1H-吡唑、2-氨基苯酚、2-氨基-6-甲基苯酚、2-氨基-5-甲基苯酚和1,2,4-三羟基苯。
除了式(1)化合物外,本发明的染料还可包含其它已知的偶合剂,例如:N-(3-二甲基氨基苯基)-脲、2,6-二氨基-吡啶、2-氨基-4-[(2-羟基乙基)氨基]苯甲醚、2,4-二氨基-1-氟-5-甲基苯、2,4氨基-1-甲氧基-5-甲基苯、2,4-二氨基-1-乙氧基-5-甲基苯、2,4-二氨基-1-(2-羟基乙氧基)-5-甲基苯、2,4-二[(2-羟基乙基)氨基]-1,5-二甲氧苯、2,3-二氨基-6-甲氧基吡啶、3-氨基-6-甲氧基-2-(甲基氨基)-吡啶、2,6-二氨基-3,5-二甲氧基-吡啶、3,5-二氨基-2,6-二甲氧基-吡啶、1,3-二氨基苯、2,4-二氨基-1-(2-羟基乙氧基)苯、1,3-二氨基-4-(2,3-二羟基丙氧基)苯、1,3-二氨基-4-(3-羟基丙氧基)苯、1,3-二氨基-4-(2-甲氧基乙氧基)苯、2,4-二氨基-1,5-二(2-羟基乙氧基)苯、1-(2-氨基乙氧基)-2-4-二氨基苯、2-氨基-1-(2-羟基乙氧基-4-甲基氨基苯、2,4-二氨基苯氧基乙酸、3-[二(2-羟基乙基)氨基]苯胺、4-氨基-2-二[(2-羟基乙基)氨基]-1-乙氧基苯、5-甲基-2-(1-甲基乙基)苯酚、3-[(2-羟基乙基)氨基]苯胺、3-[(2-氨基乙基)氨基]苯胺、1,3-二(2,4-二氨基苯氧基)丙烷、二(2,4-二氨基苯氧基)甲烷、1,3-二氨基-2,4-二甲氧基苯、2,6-双(2-羟基乙基)氨基甲苯、4-羟基吲哚、3-二甲基氨基苯酚、3-二乙基氨基苯酚、5-氨基-2-甲基苯酚、5-氨基-4-氟-2-甲基苯酚、5-氨基-4-甲氧基-2-甲基苯酚、5-氨基-4-乙氧基-2-甲基苯酚、3-氨基-2,4-二氯苯酚、5-氨基-2,4-二氯苯酚、3-氨基-2-甲基苯酚、3-氨基-2-氯-6-甲基苯酚、3-氨基苯酚、2-[(3-羟基苯基)氨基]乙酰胺、5-[(2-羟基乙基)氨基]4-甲氧基-2-甲基苯酚、5-[(2-羟基乙基)氨基]-2-甲基苯酚、3-[(2-羟基乙基)氨基]苯酚、3-[(2-甲氧基乙基氨基]苯酚、5-氨基-2-乙基苯酚、5-氨基-2-甲氧基苯酚、2-(4-氨基-2-羟基苯氧基)乙醇、5-[(3-羟基丙基)氨基]-2-甲基苯酚、3-[(2,3-二羟基丙基)氨基]-2-甲基苯酚、3-[(2-羟基乙基)氨基]-2-甲基苯酚、2-氨基-3-羟基吡啶、2,6-二羟基-3,4-二甲基吡啶、5-氨基-4-氯-2-甲基苯酚、1-萘酚、2-甲基-1-萘酚、1,5-二羟基萘、1,7-二羟基萘、2,3-二羟基萘、2,7-二羟基萘、2-甲基-1-萘酚醋酸盐、1,3-二羟基苯、1-氯-2,4-二羟基苯、2-氯-1,3-二羟基苯、1,2-二氯-3,5-二羟基-4-甲基苯、1,5-二氯-2,4-二羟基苯、1,3--二羟基-2-甲基苯、3,4-亚甲二氧基(methylenedioxy)苯酚、3,4-亚甲二氧基苯胺、5-[(2-羟基乙基)氨基]-1,3-苯并二氧戊环(benzodioxol)、6-溴-1-羟基-3,4-亚甲二氧基苯、3,4-二氨基苯甲酸、3,4-二氢-6-羟基-1,4(2H)-苯并噁嗪、6-氨基-3,4-二氢-1,4(2H)-苯并噁嗪、3-甲基-1-苯基-5-吡唑啉酮、5,6-二羟基吲哚、5,6-羟基二氢吲哚、5-羟基吲哚、6-羟基吲哚、7-羟基吲哚和2,3-二氢吲哚二酮(indolindione)。
偶合剂和显色剂在本发明的着色剂中可单独存在或者相互混合,在本发明的着色剂中每种偶合剂和显色剂的总量按重量计为约0.005%至20%、优选约0.01%至5%、尤其优选0.1%至2.5%(基于着色剂的总量)。
本发明所述的着色剂所含有的显色剂-偶合剂组合物的总量,按重量计优选为约0.01%至20%、约0.02%至10%、尤其优选0.2%至6%。显色剂和偶合剂通常以近似等摩尔的量使用。然而,如果在这方面有一些或多或少的显色剂并没有任何不利。
并且,本发明的染料也可含有其它染色组分,如6-氨基-2-甲基苯酚和2-氨基-5-甲基苯酚以及其它普通合成的或天然直接作用(directly drawing)染料,例如植物染色物质或从酸性或碱性染料、三苯甲烷染料、芳族硝基染料、偶氮染料和分散染料中直接合成的提取染料。本发明的着色剂按重量计可包含约0.1%至4%的这些染料组分。
当然,这些附加的偶合剂和显色剂以及其它的染料组分(只要它们是碱性的)也能以它们与有机酸或无机酸所形成的生理上相容的盐的形式进行使用,所述酸为例如盐酸或硫酸,或-只要它们包含芳族OH基团,就能以其与碱的盐的形式如-碱金属的酚盐进行使用。
而且,如果着色剂用于给毛发染色,它们也可包含其它常见的化妆品添加剂,例如抗氧化剂如抗坏血酸、巯基乙酸或亚硫酸钠、以及香料油、螯合剂、润湿剂、乳化剂、增稠剂和护发剂。
本发明的着色剂可以为溶液形式,例如,尤其是水溶液或含水的醇溶液。然而,尤其优选的制剂形式是霜膏、凝胶或乳液。这样的组合物由染料组分和这些组合物常用的添加剂的混合物组成。
对于溶液、霜膏、乳液或凝胶的常见添加剂为,例如溶剂,如水、低脂族醇,例如乙醇、丙醇或异丙醇、甘油或二元醇如1,2-丙二醇;还有润湿剂或乳化剂,其来自阴离子、阳离子、两性离子或非离子表面活性剂,例如脂肪醇硫酸盐、乙氧基化脂肪醇硫酸盐、烷基璜酸盐、烷基苯基璜酸盐、烷基三甲基铵盐、烷基甜菜碱、乙氧基化脂肪醇、乙氧基化壬基苯酚、脂肪酸链烷醇酰胺和乙氧基化脂族酯;还有增稠剂,如高级脂肪醇、淀粉、纤维素衍生物、凡士林、石蜡油和脂肪酸;以及护发剂,如阳离子树脂、羊毛脂衍生物、胆固醇、泛酸和甜菜碱。所述组分通常以一定含量应用于这些目的,如湿润剂和乳化剂的浓度按重量计为约0.5%至30%,增稠剂的浓度按重量计为约0.1%至30%,护发剂的浓度按重量计为约0.1%至5%。
取决于组合物,本发明的染料可以作为弱酸、中性物质或作为碱进行反应。尤其是,它的pH值为6.5至11.5,其中优选用氨进行碱性调节。然而,也可以用氨基酸和/或有机胺进行调节,例如使用一乙醇胺和三乙醇胺,或使用无机碱如氢氧化钠和氢氧化钾进行调节。适于调至酸性pH值的为无机或有机酸,例如磷酸、乙酸、柠檬酸或酒石酸。
对于毛发的氧化染色,应将上述的着色剂与氧化剂在混合后立即使用,将所得混合物应用于毛发,其量足以进行染发处理,通常为约60至200克,这取决于毛发涨满度。
用于产生染发效果的合适的氧化剂主要为过氧化氢或其加入脲、三聚氰胺、硼酸钠或碳酸钠的产物,其形式为3%至12%、优选6%的水溶液,大气中的氧也是合适的氧化剂。当使用6%的过氧化氢溶液作为氧化剂时,染发剂与氧化剂的重量比为5∶1至1∶2,但优选1∶1。当同时需要较强的毛发漂白时,主要在染发剂中较高染料浓度下使用较大量的氧化剂。让混合物在15℃至50℃下在毛发上作用约10分钟至45分钟、优选30分钟,之后用水漂洗毛发并干燥。任选地,在漂洗之后用香波洗涤毛发,任选地在漂洗后用弱有机酸漂洗,例如使用柠檬酸或酒石酸。然后干燥毛发。
本发明的着色剂包含式(1)的3-氨基苯酚衍生物作为偶合剂,可产生具有优良的毛发稳定性的毛发染色效果,尤其具有光不褪色性、洗涤不褪色性和摩擦不褪色性。就染色性质而言,本发明的染发剂提供了多种不同的色调,从金色到褐色、紫色、紫罗兰色,甚至是蓝色和黑色,这取决于染料组分的种类和组成。色调以其高颜色强度引人注意。本专利申请的染发剂的非常好的染色性质也能表明其自身的优点,因为该染发剂可以预先没有化学损伤地给灰色毛发染色而不产生任何问题,并且有良好的覆盖力。
下面的实施例用于更加详细地举例说明了本发明的目的,而不是限制本发明的范围。
实施例
实施例1至9:通式(I)的3-氨基苯酚衍生物的合成(总合成要求)
A.
3-乙氧基甲氧基苯胺的合成
在0℃向20g(183.3mmol)3-氨基苯酚的450ml无水乙腈溶液中逐渐加入12g(274.9mmol)氢化钠分散体(55%的油溶液)。然后在0℃将混合物搅拌3小时。然后将25g(210.8mmol)氯甲基乙醚溶液逐滴加入到30ml乙腈中。在室温下将混合物搅拌过夜。然后过滤反应混合物。用少量丙酮清洗过滤所得的残余物,通过蒸发浓缩滤液。得到32.3克3-乙氧基甲氧基苯胺。用这种方式得到的粗产物可用于下一步骤,不需要任何另外的清洗。
1 H-NMR(300MHz、DMSO):δ=6.89(t,1H,H5);6.24(s,1H,H2);6.22(d,1H);6.16(d,1H);5.14(s;2H,NH2);5.11(s,2H,OCH2);3.75(q,2H,CH2);1.13(t,3H,CH3)。
B.N-(3-乙氧基甲氧基苯基)氨基甲酸叔丁基酯的合成
将来自步骤A的30g(180mmol)3-乙氧基甲氧基苯胺和44.4g(203mol)二-叔丁基碳酸氢盐溶解在140ml 2N的氢氧化钠和200ml二氯甲烷的混合物中,并在室温下搅拌24小时。然后分离出有机相,用饱和氯化钠水溶液洗涤,直至pH为中性,然后用MsSO4干燥,蒸发浓缩。所得粗产物在硅胶上用己烷/乙酸乙酯(8∶1)清洗。
得到18克N-(3-乙氧基-甲氧苯基)-氨基甲酸叔丁基酯(相当于在步骤A中使用的3-氨基苯酚的理论量的42%),其为黄色油。
1 H-NMR(300MHz、DMSO):δ=9.33(s,1H,NH);7.20(s,1H,H2);7.14(t,J=8.0,1H,H5);7.05(d,J=8.0,1H,H3),6.63(d,J=8.0,1H,H6),5.17(s,2H,OCH2),3.64(q,J=7.1,2H,CH2),1.49(s,9H,叔丁基),1.13(t,J=7.1,3H,CH3)。
CHN分析:
(C14H21NO4) %C %H %N
计算值: 62.90 7.92 5.24
检测值: 62.60 8.04 4.97
C.N-(4-溴-3-乙氧基甲氧基苯基)氨基甲酸-叔丁基酯的合成
将来自步骤B的13.9g(52mmol)N-(3-乙氧基甲氧基苯基)氨基甲酸-叔丁基酯和10.2g(57.2mmol)N-溴化琥珀酰亚胺在氮气环境下溶解于400ml 1,2-二甲氧基乙烷中,并在室温下搅拌3小时。然后将反应混合物倒入到1000ml冰/水混合物中,用乙酸乙酯萃取。用饱和氯化钠水溶液洗涤有机相,然后用硫酸镁干燥。在过滤后蒸发浓缩所述有机相。所得粗产物在硅胶上用己烷/乙酸乙酯(4∶1)清洗。
得到14.4g(76%理论量)N-(4-溴-3-乙氧基甲氧基苯基)氨基甲酸-叔丁基酯,其为油。
1 H-NMR(300MHz、DMSO):δ=9.50(s,1H,NH);7.45(d,J=2.0,1H,H2);7.43(d,J=8.6,1H,H5)、7.04(dd,J=2.0,J=8.6,1H,H6);5.24(s,2H,OCH2);3.70(q,J=7.1,2H,CH2);1.48(s,9H叔丁基);1.16(t,J=7.1,3H,CH3)。
CHN分析:
(C14H20BrNO4) %C %H %N
计算值: 48.57 5.82 4.05
检测值: 47.82 5.87 3.77
D.[4-(5,5-二甲基-[1,3,2]dioxaborinane-2-基)-3-乙氧基甲氧基苯基]氨基
甲酸-叔丁基酯的合成
将来自步骤C的10g(28.8mmol)的N-(4-溴-3-乙氧基甲氧基苯基)氨基甲酸-叔丁基酯和13g(57.6mmol)5,5,5’,5’-四甲基-2,2’-二-[1,3,2-dioxaborinane]在氩气环境下溶解于260ml二噁烷中。然后,加入2.11g(2.88mmol)[1,1’-双(联苯基膦基)ferrocoen]二氯钯(II)和8.48g(86.4mmol)乙酸钾,将反应混合物在80C加热7小时。然后将反应混合物倒入1.61冰/水混合物中,用乙酸乙酯萃取。有机相用饱和的氯化钠水溶液洗涤,并用硫酸镁干燥。在过滤后蒸发浓缩所述有机相。所得粗产物在硅胶上用己烷/乙酸乙酯(2∶1)清洗。
得到5.84g(54%理论量)[4-(5,5-二甲基-[1,3,2]dioxaborinane-2-基)-3-乙氧基甲氧基苯基]-氨基甲酸-叔丁基酯。
1 H-NMR(300MHz、DMSO):δ=9.40(s,1H,NH);7.41(d,J=8.1,1H,H5);7.21(s,1H,H2);7.07(d,J=8.1,1H,H6);5.09(s,2H,OCH2);3.69(s,4H,BOCH2);3.66(q,J=7.1,2H,CH2);1.48(s,9H,叔丁基);1.18(t,3H,CH3);0.95(s,6H,CH3)。
E.式(I)的3-氨基苯酚的合成
将来自步骤D的0.23g(0.6mmol)[4-(5,5-二甲基-[1,3,2]dioxaborinane-2-基)-3-乙氧基甲氧基苯基]-氨基甲酸-叔丁基酯和0.78mmol相应的溴衍生物在氩气环境中溶解于4ml的1,2-二甲氧基乙烷中。然后加入0.07g(0.06mmol)四(三苯基膦)巴和0.8ml 2N碳酸钾溶液,将反应物加热到80C。在反应结束后,将反应混合物倒入到15ml乙酸乙酯中,用1N氢氧化钠溶液萃取有机相,然后用硫酸镁干燥。在旋转式蒸发器中蒸馏去掉溶剂,所得残余物在硅胶上用己烷/乙酸乙酯净化。将以这种方式得到的产物溶解在2ml乙醇中,用1ml 2.9摩尔盐酸的乙醇溶液稀释,或用4摩尔盐酸的二噁烷溶液稀释。然后将反应混合物加热到55C。在反应结束后,过滤沉淀物,用乙醇或二噁烷洗涤,然后干燥。
1.5-氨基-2-(3-噻吩基)苯酚盐酸盐
所使用的溴衍生物:3-溴噻吩
收率:0.032g(23%理论量)
ESI-MS:190[M-H]+(100)
2.5-氨基-2-(3-呋喃基)苯酚盐酸盐
所使用的溴衍生物:3-溴呋喃
收率:0.024g(30%理论量)
ESI-MS:174[M-H]+(100)
3.5-氨基-2-(1.3-噻唑-2-基)苯酚盐酸盐
所使用的溴衍生物:2-溴-1,3-噻唑
收率:0.029g(21%理论量)
ESI-MS:193[M-H]+(100)
4.5-氨基-2-(2-噻吩基)苯酚盐酸盐
所使用的溴衍生物:2-溴噻吩
收率:0.057g(42%理论量)
ESI-MS:190[M-H]+(100)
5.5-氨基-2-(4-甲基-3-噻吩基)苯酚盐酸盐
所使用的溴衍生物:3-溴-4-甲基噻吩
收率:0.038g(26%理论量)
ESI-MS:204[M-H]+(100)
6.5-氨基-2-(2-氯-3-噻吩基)苯酚盐酸盐
所使用的溴衍生物:3-溴-2-氯化噻吩
收率:0.056g(35%理论量)
ESI-MS:224[M-H]+(100)
1 H-NMR(300MHz、DMSO):δ=10.3(s、br、1H、OH);7.49(d、J=5.7、1H、H5’);7.29(d、J=8.1、1H、H3);7.10(d、J=5.7、1H、H4’);6.99(d、J=1.8、1H、H6);6.81(dd、J=1.8、J=8.1、1H、H4);4.10(s、br、3H、NH3+)。
CHN分析:
(C10H8NOSCl*0.94 HCl)%C %H %N %S %Cl
计算值:46.20 3.47 5.39 12.33 26.46
检测值:46.20 3.70 5.40 11.80 26.40
7.5-氨基-2-(5-氯 -2-噻吩基)苯酚盐酸盐
所使用的溴衍生物:2-溴-5-氯化噻吩
收率:0.066g(58%理论量)
ESI-MS:224[M-H]+(100)
8.5-氨基-2-(5-乙酰基-2-噻吩基)苯酚盐酸盐
所使用的溴衍生物:2-溴-5-乙酰噻吩
收率:0.060g(37%理论量)
ESI-MS:256[M+Na]+(100)
9.5-氨基-2-(5-甲酰基-2-呋喃基)苯酚盐酸盐
所使用的溴衍生物:2-溴-5-甲酰噻吩
收率:0.050g(33%理论量)
ESI-MS:202[M-H]+(100)
实施例10至18:染发剂
制备具有如下组成的染发剂溶液:
1.25mmol 按照表1的式(I)物质,
1.25mmol 按照表1的显色剂
10.0g 月桂基醚硫酸盐(28%水溶液)
9.0g 氨(22% 水溶液)
7.8g 乙醇
0.3g 抗坏血酸
0.3g 乙二胺四乙酸二钠盐水合物
至完全脱盐的100.0g 水。
将10g上述染色溶液与10g 6%的过氧化氢溶液混合后立即使用。然后将混合物应用到漂白过的毛发上。在40℃暴露30分钟后,用水漂洗毛发,用标准的商购香波洗涤,然后干燥。所得的色调示于表1中。
表1
实施例编号 | 式(I)偶合剂 | 显色剂 | |||
I.2,5-二氨基甲苯硫酸盐 | II.2,5-二氨基苯基乙醇硫酸盐 | III.4,5-二氨基-1-(2’-羟基乙基)-吡唑硫酸盐 | IV.4-氨基-3-甲基苯酚 | ||
10. | 按照实施例1 | 紫罗兰色 | 紫罗兰色 | 暗紫红色 | 浅粉红色 |
11. | 按照实施例2 | 浅灰色-紫罗兰色 | 浅灰色-紫罗兰色 | 浅红色 | 淡棕色 |
12. | 按照实施例3 | 灰色 | 灰色 | 粉红色 | 浅粉红色 |
13. | 按照实施例4 | 灰色 | 灰色 | 粉红色 | 浅粉红色 |
14. | 按照实施例5 | 浅灰色-紫罗兰色 | 浅灰色-紫罗兰色 | 浅红色 | 淡棕色 |
15. | 按照实施例6 | 深紫罗兰色 | 深紫罗兰色 | 暗紫红色 | 浅粉红色 |
16. | 按照实施例7 | 深灰色 | 深灰色 | 粉红色 | 浅粉红色 |
17. | 按照实施例8 | 绿色 | 绿色 | 粉红色 | 黄色 |
18. | 按照实施例9 | 灰金色 | 灰金色 | 浅红色 | 淡棕色 |
实施例19至24:
染发剂
制备具有如下组成的染发剂溶液:
Xg 式(I)的3-氨基苯酚衍生物
(按照表4的偶合剂K1)
Ug 按照表2的显色剂E8至E15
Yg 按照表4的偶合剂K11至K36
10.0g 月桂醚硫酸盐(28%水溶液)
9.0g 氨(22%水溶液)
7.8g 乙醇
0.3g 抗坏血酸
0.3g 乙二胺四乙酸二钠盐水合物
至100.0g完全脱盐的水。
将30g上述染色溶液与30g 6%的过氧化氢水溶液混合后立即使用。然后将混合物应用到漂白过的毛发上。在40℃暴露30分钟后,用水漂洗毛发,用标准的商购香波洗涤,然后干燥。染色效果如表5所示。
表2
显色剂 | |
E8 | 1,4-二氨基苯 |
E9 | 2,5-二氨基苯基乙醇硫酸盐 |
E10 | 3-甲基-4-氨基苯酚 |
E11 | 4-氨基-2-氨基甲基苯酚二盐酸盐 |
E13 | N,N-双(2’-羟基乙基)-对苯二胺硫酸盐 |
E14 | 4,5-二氨基-1-(2’-羟基乙基)-吡唑硫酸盐 |
E15 | 2,5-二氨基甲苯硫酸盐 |
表3
将要被直接萃取的着色剂 | |
D2 | 6-氯-2-乙基氨基-4-硝基酚 |
D3 | 2-氨基-6-氯-4-硝基酚 |
表4
偶合剂 | |
K1 | 5-氨基-2-(2-氯-3-噻吩基)苯酚 |
K12 | 2-氨基-4-(2’-羟基乙基)氨基-苯甲醚硫酸盐 |
K13 | 1,3-二氨基-4-(2’-羟基乙氧基)苯硫酸盐 |
K14 | 2,4-二氨基-5-氟代甲苯硫酸盐 |
K18 | N-(3-二甲基氨基)苯基脲脲 |
K19 | 1,3-双(2,4-二氨基苯氧基)丙烷四盐酸盐 |
K21 | 3-氨基苯酚 |
K22 | 5-氨基-2-甲基苯酚 |
K31 | 3-氨基-2-氯-6-甲基苯酚 |
K24 | 5-氨基-4-氟-2-甲基苯酚硫酸盐 |
K25 | 1-萘酚 |
K32 | 1,3-二羟基苯 |
K32 | 2-薄荷基-1,3-二羟基苯 |
K33 | 1-氯-2,4-二羟基苯 |
K34 | 4-(2’-羟基乙基)氨基-1,2-亚甲二氧基苯*HCl |
K36 | 2-氨基-5-甲基苯酚 |
表5:染发剂
实施例编号着色剂 | 19 | 20 | 21 | 22 | 23 | 24 |
(着色剂的量,以克计) | ||||||
K1 | 0.10 | 0.12 | 0.05 | 0.07 | 0.10 | 0.12 |
E8 | 0.30 | |||||
E9 | 0.25 | 0.20 | ||||
E10 | 0.10 | |||||
E15 | 0.25 | 0.30 | 0.25 | |||
K12 | 0.05 | |||||
K13 | 0.05 | |||||
K31 | 0.20 | 0.15 | 0.10 | 0.10 | ||
K32 | 0.20- | 0.10 | ||||
K33 | 0.20 | |||||
K36 | 0.10 | |||||
K21 | 0.05 | |||||
K22 | 0.05 | |||||
K23 | 0.05 | 0.10 | 0.10 | 0.10 | ||
K25 | 0.10 | |||||
染色效果 | 金色 | 金色 | 金色 | 金色 | 金色 | 金色 |
实施例25至30:染发剂
制备具有如下组成的染发剂溶液:
Xg 式(I)的3-氨基苯酚衍生物
(按照表4的偶合剂K1)
Ug 按照表2的显色剂E8至E15
Yg 按照表4的偶合剂K11至K36
Zg 按照表3的直接作用染料D2和/或D3
10.0g 月桂醚硫酸盐(28%水溶液)
9.0g 氨(22%水溶液)
7.8g 乙醇
0.3g 抗坏血酸
0.3g 乙二胺四乙酸二钠盐水合物
至完全脱盐的100.0g 水。
将30g上述染色霜膏与30g 6%的过氧化氢溶液混合后立即使用。然后将该混合物应用到毛发上。在40℃暴露30分钟后,用水漂洗毛发,用标准的商购香波洗涤,然后干燥。染色效果如表6所示。
表6 染发剂
实施例编号着色剂 | 25 | 26 | 27 | 28 | 29 | 30 |
(着色剂的量,以克计) | ||||||
K1 | 0.60 | 1.30 | 1.15 | 0.15 | 0.15 | 0.15 |
E8 | 1.50 | |||||
E11 | 0.10 | |||||
E13 | 1.60 | 0.70 | ||||
E14 | 0.10 | 0.10 | ||||
E15 | 1.80 | 0.70 | 0.70 | |||
K12 | 0.50 | |||||
K14 | 0.10 | |||||
K18 | 0.05 | |||||
K19 | 0.10 | |||||
K23 | 0.05 | 0.10 | 0.10 | 0.10 | ||
K24 | 0.15 | |||||
K31 | 0.90 | 1.10 | 1.10 | 0.40 | 0.40 | 0.40 |
K34 | 0.10 | |||||
D2 | 0.10 | 0.10 | 0.10 | |||
D3 | 0.05 | 0.05 | 0.05 | |||
染色效果 | 黑色 | 黑色 | 黑色 | 褐色 | 褐色 | 褐色 |
除非另有说明,本专利申请中所给的所有百分比都是按重量计。
Claims (13)
1.式(I)的3-氨基苯酚衍生物或其生理上相容的水溶性盐,
其中R为(Ia)的芳族五元杂环;X1、X2、X3和X4彼此独立地为硫、氮、N-R1、氧、C-R2、C-R3、C-R4或C-R5,条件为X1至X4中至少一种或最多三种为氮、N-R1、硫或氧,且如果有多个杂原子,基团X1至X4中不超过一个为硫、N-R1或氧;
R1为氢、C1-C6烷基、苯基、(C2-C4)-羟基烷基或乙酰基;
R2、R3、R4和R5彼此独立地表示氢、卤素原子(F、Cl、Br、I)、氰基、C1-C6烷基、C1-C4烷氧基、C1-C4烷基硫醚基、巯基、硝基、氨基、C1-C4烷氨基、二(C1-C4)烷氨基、羟基(C2-C4)烷氨基、二(羟基(C2-C4)烷基)氨基、(二羟基(C3-C4)烷基)氨基、三氟甲烷基、-C(O)CH3、-C(O)CF3、-C(O)H、-Si(CH3)3、(C1-C4)羟基烷基或(C2-C4)二羟基烷基。
2.如权利要求1所述的3-氨基苯酚衍生物,其特征在于所述3-氨基苯酚衍生物选自5-氨基-2-(3-噻吩基)苯酚、5-氨基-2-(3-呋喃基)苯酚、5-氨基-2-(吡咯-3-基)苯酚、5-氨基-2-(1-甲基-1H-吡咯-3-基)苯酚、5-氨基-2-(1,3-噻唑-2-基)苯酚、5-氨基-2-(1,3-噻唑-5-基)苯酚、5-氨基-2-(2-噻吩基)苯酚、5-氨基-2-(2-呋喃基)苯酚、5-氨基-2-(吡咯-2-基)苯酚、5-氨基-2-(1-甲基-1H-吡咯-2-基)苯酚、5-氨基-2-(2-氯-3-噻吩基)苯酚、5-氨基-2-(2-甲基-3-噻吩基)苯酚、5-氨基-2-(2-硝基-3-噻吩基)苯酚、5-氨基-2-(2-氨基-3-噻吩基)苯酚、5-氨基-2-(2-乙酰基-3-噻吩基)-苯酚、5-氨基-2-(2-甲酰基-3-噻吩基)苯酚、5-氨基-2-(4-氯-3-噻吩基)苯酚、5-氨基-2-(4-甲基-3-噻吩基)苯酚、5-氨基-2-(4-硝基-3-噻吩基)苯酚、5-氨基-2-(4-氨基-3-噻吩基)苯酚、5-氨基-2-(4-乙酰基-3-噻吩基)苯酚、5-氨基-2-(4-甲酰基-3-噻吩基)苯酚、5-氨基-2-(5-氟-3-噻吩基)苯酚、5-氨基-2-(5-甲基-3-噻吩基)苯酚、5-氨基-2-(5-硝基-3-噻吩基)苯酚,5-氨基-2-(5-乙酰基-3-噻吩基)苯酚、5-氨基-2-(5-氨基-3-噻吩基)苯酚、5-氨基-2-(5-甲酰基-3-噻吩基)苯酚、5-氨基-2-(5-甲酰基-3-呋喃基)苯酚、5-氨基-2-(3-氯-2-噻吩基)苯酚、5-氨基-2-(3-甲基-2-噻吩基)苯酚、5-氨基-2-(3-硝基-2-噻吩基)苯酚、5-氨基-2-(3-氨基-2-噻吩基)苯酚、5-氨基-2-(3-乙酰基-2-噻吩基)-苯酚、5-氨基-2-(3-甲酰基-2-噻吩基)苯酚、5-氨基-2-(4-氯-2-噻吩基)苯酚、5-氨基-2-(4-甲基-2-噻吩基)苯酚、5-氨基-2-(4-硝基-2-噻吩基)苯酚、5-氨基-2-(4-氨基-2-噻吩基)苯酚、5-氨基-2-(4-乙酰基-2-噻吩基)苯酚、5-氨基-2-(4-甲酰基-2-噻吩基)苯酚、5-氨基-2-(5-氯-2-噻吩基)苯酚、5-氨基-2-(5-甲基-2-噻吩基)苯酚、5-氨基-2-(5-硝基-2-噻吩基)苯酚、5-氨基-2-(5-氨基-2-噻吩基)苯酚、5-氨基-2-(5-乙酰基-2-噻吩基)-苯酚、5-氨基-2-(5-甲酰基-2-噻吩基)苯酚、5-氨基-2-(5-甲酰基-2-呋喃基)苯酚、5-氨基-2-(5-硝基-1,3-噻唑-2-基)苯酚、5-氨基-2-(5-氨基-1,3-噻唑-2-基)苯酚、5-氨基-2-(2-硝基-1,3-噻唑-5-基)苯酚、5-氨基-2-(2-氨基-1,3-噻唑-5-基)苯酚、5-氨基-2-(3,5-二甲基-1H-吡唑-4-基)苯酚和5-氨基-2-(5-硝基-4H-1,2,4-三唑-3-基)苯酚及其生理上相容的水溶性盐。
3.如权利要求1所述的3-氨基苯酚衍生物,其特征在于式(I)满足如下条件:
(i)X2为硫,而X1、X3和X4为C-R2、C-R4和C-R5;或(ii)X1为硫,且X2、X3和X4为C-R3、C-R4和C-R5。
4.如权利要求1至3中任一项所述的3-氨基苯酚衍生物,其特征在于所述3-氨基苯酚衍生物选自5-氨基-2-(3-噻吩基)苯酚、5-氨基-2-(2-氯-3-噻吩基)苯酚和5-氨基-2-(5-氯-2-噻吩基)苯酚及其生理上相容的盐。
5.基于显色剂/偶合剂组合的用于给角蛋白纤维染色的试剂,其特征在于所述试剂作为偶合剂包含至少一种如权利要求1至4中任一项所述的式(I)的3-氨基苯酚衍生物。
6.如权利要求5所述的试剂,其特征在于所述试剂包含按重量计0.005%至20%重量的式(I)的3-氨基苯酚衍生物。
7.如权利要求书5或6所述的试剂,其特征在于所述显色剂选自1,4-二氨基苯、1,4-二氨基-2-甲基苯、1,4-二氨基-2,6-二甲基苯、1,4-二氨基-3,5-二乙基苯、1,4-二氨基-2,5-二甲基苯、1,4-二氨基-2,3-二甲基苯、2-氯-1,4-二氨基苯、1,4-二氨基-2-(噻吩-2-基)苯、1,4-二氨基-2-(噻吩-3-基)苯、1,4-二氨基-2-(吡啶-3-基)苯、2,5-二氨基联苯、1,4-二氨基-2-甲氧基甲基苯、1,4-二氨基-2-氨基甲基苯、1,4-二氨基-2-羟基甲基苯、1,4-二氨基-2-(2-羟基乙氧基)苯、2-(2-(乙酰氨基)乙氧基)-1,4-二氨基苯、4-苯基氨基苯胺、4-二甲基氨基苯胺、4-二乙基氨基苯胺、4-二丙基氨基苯胺、4-[乙基(2-羟基乙基)-氨基]-苯胺、4-[二(2-羟基乙基)氨基]苯胺、4-[二(2-羟基乙基)氨基]-2-甲基苯胺、4-[(2-甲氧基乙基)氨基]苯胺、4-[(3-羟丙基)氨基]苯胺、4-[(2,3-二羟基丙基)氨基]苯胺、1,4-二氨基-2-(1-羟基乙基)苯、1,4-二氨基-2-(2-羟基乙基)苯、1,4-二氨基-2-(1-甲基乙基)苯、1,3-双[(4-氨基苯基)(2-羟基乙基)氨基]-2-丙醇、1,4-双[(4-氨基苯基)氨基]丁烷、1,8-双(2,5-二氨基苯氧基)-3,6-二氧杂辛烷、4-氨基苯酚、4-氨基-3-甲基苯酚、4-氨基-3-(羟甲基)苯酚、4-氨基-3-氟苯酚、4-甲基氨基苯酚、4-氨基-2-(氨基甲基)苯酚、4-氨基-2-(羟甲基)苯酚、4-氨基-2-氟苯酚、4-氨基-2-[(2-羟基乙基)氨基]甲基苯酚、4-氨基-2-甲基苯酚、4-氨基-2-(甲氧基甲基)苯酚、4-氨基-2-(2-羟基乙基)苯酚、5-氨基水杨酸、2,5-二氨基吡啶、2,4,5,6-四氨基嘧啶、2,5,6-三氨基-4-(1H)-嘧啶酮、4,5-二氨基-1-(2-羟基乙基)-1H-吡唑、4,5-二氨基-1-(1-甲基乙基)-1H-吡唑、4,5-二氨基-1-[(4-甲基苯基)甲基]-1H-吡唑、1-[(4-氯代苯基)甲基]-4,5-二氨基-1H-吡唑、4,5-二氨基-1-甲基-1H-吡唑、2-氨基苯酚、2-氨基-6-甲基苯酚、2-氨基-5-甲基苯酚和1,2,4-三羟基苯。
8.如权利要求5至7中任一项所述的试剂,其特征在于除了式(I)的化合物之外,所述试剂还包含至少一种其它的已知偶合剂,所述偶合剂选自N-(3-二甲基氨基苯基)-脲、2,6-二氨基-吡啶、2-氨基-4-[(2-羟基乙基)氨基]苯甲醚、2,4-二氨基-1-氟-5-甲基苯、2,4-二氨基-1-甲氧基-5-甲基苯、2,4-二氨基-1-乙氧基-5-甲基苯、2,4-二-氨基-1-(2-羟基乙氧基)-5-甲基苯、2,4-二[(2-羟基乙基)氨基]-1,5-二甲氧苯、2,3-二氨基-6-甲氧基吡啶、3-氨基-6-甲氧基-2-(甲基氨基)-吡啶、2,6-二氨基-3,5-二甲氧基吡啶、3,5-二氨基-2,6-二甲氧基吡啶、1,3-二氨基苯、2,4-二氨基-1-(2-羟基乙氧基)苯、1,3-二氨基-4-(2,3-二羟基丙氧基)苯、1,3-二氨基-4-(3-羟基丙氧基)苯、1,3-二氨基-4-(2-甲氧基乙氧基)苯、2,4-二氨基-1,5-二(2-羟基乙氧基)苯、1-(2-氨基乙氧基)-2,4-二氨基苯、2-氨基-1-(2-羟基乙氧基)-4-甲基氨基苯、2,4-二-氨基苯氧基乙酸、3-[二(2-羟基乙基)氨基]苯胺、4-氨基-2-二[(2-羟基乙基)氨基]-1-乙氧基苯、5-甲基-2-(1-甲基乙基)苯酚、3-[(2-羟基乙基)氨基]苯胺、3-[(2-氨基乙基)氨基]苯胺、1,3-二(2,4-二氨基苯氧基)丙烷、二(2,4-二氨基苯氧基)甲烷、1,3-二氨基-2,4-二甲氧基苯、2,6-双(2-羟基乙基)氨基甲苯、4-羟基吲哚、3-二甲基氨基苯酚、3-二乙基氨基苯酚、5-氨基-2-甲基苯酚、5-氨基-4-氟-2-甲基苯酚、5-氨基-4-甲氧基-2-甲基苯酚、5-氨基-4-乙氧基-2-甲基苯酚、3-氨基-2,4-二氯苯酚、5-氨基-2,4-二氯苯酚、3-氨基-2-甲基苯酚、3-氨基-2-氯-6-甲基苯酚、3-氨基苯酚、2-[(3-羟基苯基)氨基]乙酰胺、5-[(2-羟基乙基)氨基]-4-甲氧基-2-甲基苯酚、5-[(2-羟基乙基)氨基]-2-甲基苯酚、3-[(2-羟基乙基)氨基]苯酚、3-[(2-甲氧基乙基)氨基]苯酚、5-氨基-2-乙基苯酚、5-氨基-2-甲氧基苯酚、2-(4-氨基-2-羟基苯氧基)乙醇、5-[(3-羟基丙基)氨基]-2-甲基苯酚、3-[(2,3-二羟基丙基)氨基]-2-甲基苯酚、3-[(2-羟基乙基)氨基]-2-甲基苯酚、2-氨基-3-羟基吡啶、2,6-二羟基-3,4-二甲基吡啶、5-氨基-4-氯-2-甲基苯酚、1-萘酚、2-甲基-1-萘酚、1,5-二羟基萘、1,7-二羟基萘、2,3-二羟基萘、2,7-二羟基萘、2-甲基-1-萘酚醋酸盐、1,3-二羟基苯、1-氯-2,4-二羟基苯、2-氯-1,3-二羟基苯、1,2-二氯-3,5-二羟基-4-甲基苯、1,5-二氯-2,4-二羟基苯、1,3-二羟基-2-甲基苯、3,4-亚甲二氧基苯酚、3,4-亚甲二氧基苯胺、5-[(2-羟基乙基)氨基]-1,3-苯并二氧戊环、6-溴代-1-羟基-3,4-亚甲二氧基苯、3,4-二氨基苯甲酸、3,4-二氢-6-羟基-1,4(2H)-苯并噁嗪、6-氨基-3,4-二氢-1,4(2H)-苯并噁嗪、3-甲基-1-苯基-5-吡唑啉酮、5,6-二羟基吲哚、5,6-羟基二氢吲哚、5-羟基吲哚、6-羟基吲哚、7-羟基吲哚和2,3-二氢吲哚二酮。
9.如权利要求5至8中任一项所述的试剂,其特征在于所述试剂包含各种显色剂和偶合剂,其总量按所述染色剂的总量计为0.005%至20%重量。
10.如权利要求5至9中任一项所述的试剂,其特征在于所述试剂另外包含至少一种直接作用着色剂。
11.如权利要求5至10中任一项所述的试剂,其特征在于所述试剂的pH值为6.5至11.5。
12.准备用于对角蛋白纤维进行氧化性染色的试剂,所述试剂在适于染色的介质中包含至少一种显色剂和至少一种偶合剂,其特征在于所述试剂包含至少一种式(I)的3-氨基苯酚衍生物作为如权利要求1-4中任一项所述的偶合剂。
13.如权利要求5至12中任一项所述的试剂,其特征在于所述试剂为染发剂。
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DE10141723A DE10141723A1 (de) | 2001-08-25 | 2001-08-25 | m-Aminophenol-Derivate und diese Verbindung enthaltende Färbemittel |
DE10141723.3 | 2001-08-25 |
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US (1) | US7128764B2 (zh) |
EP (1) | EP1419148B1 (zh) |
JP (1) | JP2005502669A (zh) |
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AU (1) | AU2002302566B2 (zh) |
BR (1) | BR0211389A (zh) |
CA (1) | CA2458681A1 (zh) |
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CN101863860B (zh) * | 2009-04-16 | 2013-07-10 | 上海药明康德新药开发有限公司 | 2-氟-4-取代氨基苯胺的合成方法 |
CN106634174A (zh) * | 2016-12-26 | 2017-05-10 | 海宁市佳峰彩印包装有限公司 | 一种生物可降解彩印油墨助剂 |
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DE102004035164A1 (de) * | 2004-07-20 | 2006-02-09 | Wella Ag | Neue o-Aminophenol-Derivate und diese Verbindungen enthaltende Färbemittel |
DE102006026038A1 (de) * | 2006-06-01 | 2007-12-06 | Henkel Kgaa | Aufhell- und/oder Färbemittel mit cyclischen Harnstoffderivaten |
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DE2118494C3 (de) | 1971-04-16 | 1980-04-24 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Diarylverbindungen |
US5019130A (en) * | 1989-11-03 | 1991-05-28 | Clairol Incorporated | Substituted N-aryl pyrroles in oxidative hair dye compositions |
CN1162915A (zh) * | 1994-11-17 | 1997-10-22 | 汉克尔股份两合公司 | 氧化染料 |
FR2739554B1 (fr) * | 1995-10-06 | 1998-01-16 | Oreal | Composition pour la teinture d'oxydation des fibres keratiniques comprenant de la 2-amino 3-hydroxy pyridine et une base d'oxydation, et procede de teinture |
DE19812058C1 (de) | 1998-03-19 | 1999-10-07 | Wella Ag | Diaminobenzol-Derivate und diese Verbindungen enthaltende Haarfärbemittel |
DE10022829B4 (de) * | 2000-05-10 | 2004-02-05 | Wella Ag | p-Aminophenol-Derivate und diese Verbindungen enthaltende Haarfärbemittel |
DE10022828A1 (de) | 2000-05-10 | 2001-11-22 | Wella Ag | Neue p-Aminophenole und diese Verbindungen enthaltende Färbemittel |
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2001
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- 2002-04-24 BR BR0211389-9A patent/BR0211389A/pt active Pending
- 2002-04-24 US US10/487,627 patent/US7128764B2/en not_active Expired - Fee Related
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- 2002-04-24 DE DE50208161T patent/DE50208161D1/de not_active Expired - Fee Related
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CN101863860B (zh) * | 2009-04-16 | 2013-07-10 | 上海药明康德新药开发有限公司 | 2-氟-4-取代氨基苯胺的合成方法 |
CN106634174A (zh) * | 2016-12-26 | 2017-05-10 | 海宁市佳峰彩印包装有限公司 | 一种生物可降解彩印油墨助剂 |
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AU2002302566B2 (en) | 2006-09-21 |
DE50208161D1 (de) | 2006-10-26 |
BR0211389A (pt) | 2004-08-17 |
MXPA04001442A (es) | 2004-05-27 |
ES2272714T3 (es) | 2007-05-01 |
WO2003018571A1 (de) | 2003-03-06 |
CA2458681A1 (en) | 2003-03-06 |
EP1419148A1 (de) | 2004-05-19 |
US20040237214A1 (en) | 2004-12-02 |
DE10141723A1 (de) | 2003-03-06 |
US7128764B2 (en) | 2006-10-31 |
JP2005502669A (ja) | 2005-01-27 |
CN100358887C (zh) | 2008-01-02 |
ATE339412T1 (de) | 2006-10-15 |
EP1419148B1 (de) | 2006-09-13 |
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