CH625540A5 - - Google Patents
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- Publication number
- CH625540A5 CH625540A5 CH449477A CH820575A CH625540A5 CH 625540 A5 CH625540 A5 CH 625540A5 CH 449477 A CH449477 A CH 449477A CH 820575 A CH820575 A CH 820575A CH 625540 A5 CH625540 A5 CH 625540A5
- Authority
- CH
- Switzerland
- Prior art keywords
- hydrogen
- alkyl
- chlorine
- formula
- trifluoromethyl
- Prior art date
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- 239000000460 chlorine Substances 0.000 claims description 133
- -1 benzylsulfonyl Chemical group 0.000 claims description 91
- 229910052739 hydrogen Inorganic materials 0.000 claims description 65
- 239000001257 hydrogen Substances 0.000 claims description 62
- 150000002431 hydrogen Chemical class 0.000 claims description 41
- 239000000975 dye Substances 0.000 claims description 36
- 229910052801 chlorine Inorganic materials 0.000 claims description 32
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 26
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 25
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 25
- 229910052794 bromium Inorganic materials 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000004799 bromophenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- 239000000987 azo dye Substances 0.000 claims 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 230000008878 coupling Effects 0.000 description 24
- 238000010168 coupling process Methods 0.000 description 24
- 238000005859 coupling reaction Methods 0.000 description 24
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 23
- 239000000243 solution Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000004952 Polyamide Substances 0.000 description 9
- 229920002647 polyamide Polymers 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000002475 indoles Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- SJCTXIKOXTUQHC-UHFFFAOYSA-N 4-amino-2,5-dichlorobenzenesulfonic acid Chemical compound NC1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl SJCTXIKOXTUQHC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 229910004385 CaHg Inorganic materials 0.000 description 3
- 229910006069 SO3H Inorganic materials 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 229960003080 taurine Drugs 0.000 description 3
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000005140 aralkylsulfonyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- IXHXCUJPSCLUOZ-UHFFFAOYSA-N 1-(2-acetyloxybutyl)-2-phenyl-3h-indole-2-sulfonic acid Chemical compound CC(=O)OC(CC)CN1C2=CC=CC=C2CC1(S(O)(=O)=O)C1=CC=CC=C1 IXHXCUJPSCLUOZ-UHFFFAOYSA-N 0.000 description 1
- QDCTWKZPRVIHFJ-UHFFFAOYSA-N 1-(2-ethoxycarbonyloxybutyl)-2-phenyl-3h-indole-2-sulfonic acid Chemical compound CCOC(=O)OC(CC)CN1C2=CC=CC=C2CC1(S(O)(=O)=O)C1=CC=CC=C1 QDCTWKZPRVIHFJ-UHFFFAOYSA-N 0.000 description 1
- FXIKUFQNKPDAON-UHFFFAOYSA-N 1-(2-hydroxy-2-methylpropyl)-2-methyl-3h-indole-2-sulfonic acid Chemical compound C1=CC=C2CC(S(O)(=O)=O)(C)N(CC(C)(O)C)C2=C1 FXIKUFQNKPDAON-UHFFFAOYSA-N 0.000 description 1
- FYEOODODUAGSEF-UHFFFAOYSA-N 1-(2-hydroxy-2-phenylethyl)-2-methyl-3h-indole-2-sulfonic acid Chemical compound OS(=O)(=O)C1(C)CC2=CC=CC=C2N1CC(O)C1=CC=CC=C1 FYEOODODUAGSEF-UHFFFAOYSA-N 0.000 description 1
- QRPPHOOUMNSZPO-UHFFFAOYSA-N 1-(2-hydroxy-2-phenylethyl)-2-phenyl-3h-indole-2-sulfonic acid Chemical compound C=1C=CC=CC=1C(O)CN1C2=CC=CC=C2CC1(S(O)(=O)=O)C1=CC=CC=C1 QRPPHOOUMNSZPO-UHFFFAOYSA-N 0.000 description 1
- GUHUPIXXESJPII-UHFFFAOYSA-N 1-(2-methylindol-1-yl)-3-phenoxypropan-2-ol Chemical compound CC1=CC2=CC=CC=C2N1CC(O)COC1=CC=CC=C1 GUHUPIXXESJPII-UHFFFAOYSA-N 0.000 description 1
- WFWYAXHPHVICFQ-UHFFFAOYSA-N 1-(2-methylindol-1-yl)butan-2-ol Chemical compound C1=CC=C2N(CC(O)CC)C(C)=CC2=C1 WFWYAXHPHVICFQ-UHFFFAOYSA-N 0.000 description 1
- WYNXEYLPROKVHL-UHFFFAOYSA-N 1-(2-methylindol-1-yl)pentan-2-ol Chemical compound C1=CC=C2N(CC(O)CCC)C(C)=CC2=C1 WYNXEYLPROKVHL-UHFFFAOYSA-N 0.000 description 1
- OFMKRQDIPVYFPD-UHFFFAOYSA-N 1-(2-methylindol-1-yl)propan-2-ol Chemical compound C1=CC=C2N(CC(O)C)C(C)=CC2=C1 OFMKRQDIPVYFPD-UHFFFAOYSA-N 0.000 description 1
- UAEKAWNVIJJUEO-UHFFFAOYSA-N 1-(4-aminophenyl)sulfonylbutane-1-sulfonamide Chemical compound CCCC(S(N)(=O)=O)S(=O)(=O)C1=CC=C(N)C=C1 UAEKAWNVIJJUEO-UHFFFAOYSA-N 0.000 description 1
- RXIHYQPZEOPKQP-UHFFFAOYSA-N 1-(5-amino-2-methoxyphenyl)sulfonylbutane-1-sulfonamide Chemical compound CCCC(S(N)(=O)=O)S(=O)(=O)C1=CC(N)=CC=C1OC RXIHYQPZEOPKQP-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- WRTAZRGRFBCKBU-UHFFFAOYSA-N 2,5-dibromoaniline Chemical compound NC1=CC(Br)=CC=C1Br WRTAZRGRFBCKBU-UHFFFAOYSA-N 0.000 description 1
- YUTLYGKUNOZFSA-UHFFFAOYSA-N 2,5-dichloro-4-propylsulfonylaniline Chemical compound CCCS(=O)(=O)C1=CC(Cl)=C(N)C=C1Cl YUTLYGKUNOZFSA-UHFFFAOYSA-N 0.000 description 1
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
- ITPONWUGXOFQFP-UHFFFAOYSA-N 2-(2-methylindol-1-yl)-1-phenylethanol Chemical compound CC1=CC2=CC=CC=C2N1CC(O)C1=CC=CC=C1 ITPONWUGXOFQFP-UHFFFAOYSA-N 0.000 description 1
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 1
- LJMWEDRULGPOHN-UHFFFAOYSA-N 2-[(3-amino-4-chlorophenyl)sulfonylmethyl]benzenesulfonamide Chemical compound C1=C(Cl)C(N)=CC(S(=O)(=O)CC=2C(=CC=CC=2)S(N)(=O)=O)=C1 LJMWEDRULGPOHN-UHFFFAOYSA-N 0.000 description 1
- FWBMULBKJVVFQA-UHFFFAOYSA-N 2-[(4-amino-2-chlorophenyl)sulfonylamino]ethanesulfonic acid Chemical compound NC1=CC=C(S(=O)(=O)NCCS(O)(=O)=O)C(Cl)=C1 FWBMULBKJVVFQA-UHFFFAOYSA-N 0.000 description 1
- UWXGAKUYWRLACI-UHFFFAOYSA-N 2-[(4-amino-3-methoxyphenyl)sulfonylamino]ethanesulfonic acid Chemical compound COC1=CC(S(=O)(=O)NCCS(O)(=O)=O)=CC=C1N UWXGAKUYWRLACI-UHFFFAOYSA-N 0.000 description 1
- KGGBZDCVGOMYJM-UHFFFAOYSA-N 2-[(4-aminophenyl)sulfonyl-methylamino]ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(C)S(=O)(=O)C1=CC=C(N)C=C1 KGGBZDCVGOMYJM-UHFFFAOYSA-N 0.000 description 1
- GMHNHZUBZVEINK-UHFFFAOYSA-N 2-[(4-aminophenyl)sulfonyl-propylamino]ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(CCC)S(=O)(=O)C1=CC=C(N)C=C1 GMHNHZUBZVEINK-UHFFFAOYSA-N 0.000 description 1
- HBJXAVXFXDAEDI-UHFFFAOYSA-N 2-[(4-aminophenyl)sulfonylmethyl]benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)CC1=CC=CC=C1S(N)(=O)=O HBJXAVXFXDAEDI-UHFFFAOYSA-N 0.000 description 1
- KDIJBFXQTXIRQP-UHFFFAOYSA-N 2-[4-amino-2-chloro-5-(trifluoromethyl)phenyl]sulfonylbenzenesulfonamide Chemical compound C1=C(C(F)(F)F)C(N)=CC(Cl)=C1S(=O)(=O)C1=CC=CC=C1S(N)(=O)=O KDIJBFXQTXIRQP-UHFFFAOYSA-N 0.000 description 1
- OXEFYSAEZDUHOA-UHFFFAOYSA-N 2-[[4-amino-3-(trifluoromethyl)phenyl]sulfonylmethyl]benzenesulfonamide Chemical compound C1=C(C(F)(F)F)C(N)=CC=C1S(=O)(=O)CC1=CC=CC=C1S(N)(=O)=O OXEFYSAEZDUHOA-UHFFFAOYSA-N 0.000 description 1
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 1
- NTUOGJBZISFLJX-UHFFFAOYSA-N 2-chloro-4-ethylsulfonylaniline Chemical compound CCS(=O)(=O)C1=CC=C(N)C(Cl)=C1 NTUOGJBZISFLJX-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- GQXQAHCLADNGCS-UHFFFAOYSA-N 2-methyl-1-(2-methylindol-1-yl)propan-2-ol Chemical compound C1=CC=C2N(CC(C)(C)O)C(C)=CC2=C1 GQXQAHCLADNGCS-UHFFFAOYSA-N 0.000 description 1
- XYSBZXSDYOSTFK-UHFFFAOYSA-N 2-methylindole-2-sulfonic acid Chemical compound C1=CC=CC2=NC(C)(S(O)(=O)=O)C=C21 XYSBZXSDYOSTFK-UHFFFAOYSA-N 0.000 description 1
- CYHMAWOTYKYTGQ-UHFFFAOYSA-N 3-(chloroamino)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(NCl)=C1 CYHMAWOTYKYTGQ-UHFFFAOYSA-N 0.000 description 1
- SCIUYSRKWFTKHU-UHFFFAOYSA-N 3-[(4-amino-2,5-dichlorophenyl)sulfonylamino]propane-1-sulfonic acid Chemical compound NC1=CC(Cl)=C(S(=O)(=O)NCCCS(O)(=O)=O)C=C1Cl SCIUYSRKWFTKHU-UHFFFAOYSA-N 0.000 description 1
- ZLZFHMRJYDCJHP-UHFFFAOYSA-N 3-[(4-amino-2-chlorophenyl)sulfonylamino]propane-1-sulfonic acid Chemical compound NC1=CC=C(S(=O)(=O)NCCCS(O)(=O)=O)C(Cl)=C1 ZLZFHMRJYDCJHP-UHFFFAOYSA-N 0.000 description 1
- GUAUCJCGFLUHML-UHFFFAOYSA-N 3-[(4-amino-3,5-dichlorophenyl)sulfonylamino]propane-1-sulfonic acid Chemical compound NC1=C(Cl)C=C(S(=O)(=O)NCCCS(O)(=O)=O)C=C1Cl GUAUCJCGFLUHML-UHFFFAOYSA-N 0.000 description 1
- URPRJIFSPRBOIH-UHFFFAOYSA-N 3-amino-4-chloro-N-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)NS(=O)(=O)C1=CC(=C(C=C1)Cl)N URPRJIFSPRBOIH-UHFFFAOYSA-N 0.000 description 1
- VSMASPJOYQOMMS-UHFFFAOYSA-N 3-amino-N-butylsulfonyl-4-chlorobenzenesulfonamide Chemical compound C(CCC)S(=O)(=O)NS(=O)(=O)C1=CC(=C(C=C1)Cl)N VSMASPJOYQOMMS-UHFFFAOYSA-N 0.000 description 1
- DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 description 1
- GCBXHNPPKAIMAT-UHFFFAOYSA-N 4-[(4-amino-3-chlorophenyl)sulfonylmethyl]benzenesulfonamide Chemical compound C1=C(Cl)C(N)=CC=C1S(=O)(=O)CC1=CC=C(S(N)(=O)=O)C=C1 GCBXHNPPKAIMAT-UHFFFAOYSA-N 0.000 description 1
- SEDCMAXUTJDSBN-UHFFFAOYSA-N 4-[(4-aminophenyl)sulfonylmethyl]benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)CC1=CC=C(S(N)(=O)=O)C=C1 SEDCMAXUTJDSBN-UHFFFAOYSA-N 0.000 description 1
- BHFJCOQYWNOYAI-UHFFFAOYSA-N 4-[[4-amino-3-(trifluoromethyl)phenyl]sulfonylmethyl]benzenesulfonamide Chemical compound C1=C(C(F)(F)F)C(N)=CC=C1S(=O)(=O)CC1=CC=C(S(N)(=O)=O)C=C1 BHFJCOQYWNOYAI-UHFFFAOYSA-N 0.000 description 1
- HEAIMPIBXMBVMK-UHFFFAOYSA-N 4-amino-2,5-dibromobenzenesulfonic acid Chemical compound NC1=CC(Br)=C(S(O)(=O)=O)C=C1Br HEAIMPIBXMBVMK-UHFFFAOYSA-N 0.000 description 1
- KBQAZLXJUFGPPI-UHFFFAOYSA-N 4-amino-2,5-dichloro-n,n-diethylbenzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC(Cl)=C(N)C=C1Cl KBQAZLXJUFGPPI-UHFFFAOYSA-N 0.000 description 1
- MICDVUDJBHIFHA-UHFFFAOYSA-N 4-amino-2,5-dimethoxybenzenesulfonic acid Chemical compound COC1=CC(S(O)(=O)=O)=C(OC)C=C1N MICDVUDJBHIFHA-UHFFFAOYSA-N 0.000 description 1
- LZLJAEOYTHSSJR-UHFFFAOYSA-N 4-amino-2-chloro-N-methylsulfonyl-5-(trifluoromethyl)benzenesulfonamide Chemical compound FC(C=1C=C(C(=CC1N)Cl)S(=O)(=O)NS(=O)(=O)C)(F)F LZLJAEOYTHSSJR-UHFFFAOYSA-N 0.000 description 1
- ZDIRCGKEOWZBIM-UHFFFAOYSA-N 4-amino-2-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=CC=C1S(O)(=O)=O ZDIRCGKEOWZBIM-UHFFFAOYSA-N 0.000 description 1
- LRUMKMXIIBGAIN-UHFFFAOYSA-N 4-amino-3,5-dicyanobenzenesulfonic acid Chemical compound NC1=C(C#N)C=C(S(O)(=O)=O)C=C1C#N LRUMKMXIIBGAIN-UHFFFAOYSA-N 0.000 description 1
- CVYDAAGFDZATJD-UHFFFAOYSA-N 4-amino-3-bromobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1Br CVYDAAGFDZATJD-UHFFFAOYSA-N 0.000 description 1
- KJCZHTFQLGOCPM-UHFFFAOYSA-N 4-amino-3-chloro-N-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)NS(=O)(=O)C1=CC(=C(C=C1)N)Cl KJCZHTFQLGOCPM-UHFFFAOYSA-N 0.000 description 1
- MGCBZYGCHKJBAH-UHFFFAOYSA-N 4-amino-3-chloro-n-(dimethylsulfamoyl)benzenesulfonamide Chemical compound CN(C)S(=O)(=O)NS(=O)(=O)C1=CC=C(N)C(Cl)=C1 MGCBZYGCHKJBAH-UHFFFAOYSA-N 0.000 description 1
- WQTCZINVPXJNEL-UHFFFAOYSA-N 4-amino-3-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=CC=C1N WQTCZINVPXJNEL-UHFFFAOYSA-N 0.000 description 1
- AZNLFCLBCQULET-UHFFFAOYSA-N 4-amino-N-(benzenesulfonyl)-2,5-dichlorobenzenesulfonamide Chemical compound C1=C(Cl)C(N)=CC(Cl)=C1S(=O)(=O)NS(=O)(=O)C1=CC=CC=C1 AZNLFCLBCQULET-UHFFFAOYSA-N 0.000 description 1
- OGHDYYCSMDCJSB-UHFFFAOYSA-N 4-amino-N-(benzenesulfonyl)-3-chlorobenzenesulfonamide Chemical compound C1(=CC=CC=C1)S(=O)(=O)NS(=O)(=O)C1=CC(=C(C=C1)N)Cl OGHDYYCSMDCJSB-UHFFFAOYSA-N 0.000 description 1
- SMLGYQHLDNPTHC-UHFFFAOYSA-N 4-amino-N-(benzenesulfonyl)-3-methylbenzenesulfonamide Chemical compound CC1=C(N)C=CC(=C1)S(=O)(=O)NS(=O)(=O)C1=CC=CC=C1 SMLGYQHLDNPTHC-UHFFFAOYSA-N 0.000 description 1
- YRLQSRLDUYSZAF-UHFFFAOYSA-N 4-amino-N-methylsulfonyl-3-(trifluoromethyl)benzenesulfonamide Chemical compound CS(=O)(=O)NS(=O)(=O)C1=CC(=C(C=C1)N)C(F)(F)F YRLQSRLDUYSZAF-UHFFFAOYSA-N 0.000 description 1
- NIYDCVIOYUJLEJ-UHFFFAOYSA-N 4-amino-n-(benzenesulfonyl)-3-(trifluoromethyl)benzenesulfonamide Chemical compound C1=C(C(F)(F)F)C(N)=CC=C1S(=O)(=O)NS(=O)(=O)C1=CC=CC=C1 NIYDCVIOYUJLEJ-UHFFFAOYSA-N 0.000 description 1
- LMDQYIJWAFDUNA-UHFFFAOYSA-N 4-amino-n-methyl-3-(trifluoromethyl)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N)C(C(F)(F)F)=C1 LMDQYIJWAFDUNA-UHFFFAOYSA-N 0.000 description 1
- XQVHEDUZPHPUKA-UHFFFAOYSA-N 4-amino-n-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)NS(=O)(=O)C1=CC=C(N)C=C1 XQVHEDUZPHPUKA-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- OVGZSYUPUWEPFZ-UHFFFAOYSA-N 4-benzylsulfonylaniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)CC1=CC=CC=C1 OVGZSYUPUWEPFZ-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- DWOIGSLSPPLRKO-UHFFFAOYSA-N 4-propoxyaniline Chemical compound CCCOC1=CC=C(N)C=C1 DWOIGSLSPPLRKO-UHFFFAOYSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- LVRCEUVOXCJYSV-UHFFFAOYSA-N CN(C)S(=O)=O Chemical compound CN(C)S(=O)=O LVRCEUVOXCJYSV-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-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
- 101100206738 Mus musculus Tiam2 gene Proteins 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000005100 aryl amino carbonyl group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- YKTNMVAQSYBBMK-UHFFFAOYSA-N ethyl 1-(2-phenylindol-1-yl)butan-2-yl carbonate Chemical compound C=1C2=CC=CC=C2N(CC(CC)OC(=O)OCC)C=1C1=CC=CC=C1 YKTNMVAQSYBBMK-UHFFFAOYSA-N 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- JZSUOTJWYOXCKT-UHFFFAOYSA-N n-[4-amino-3-(trifluoromethyl)phenyl]sulfonylnaphthalene-2-sulfonamide Chemical compound C1=C(C(F)(F)F)C(N)=CC=C1S(=O)(=O)NS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 JZSUOTJWYOXCKT-UHFFFAOYSA-N 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/11—Preparation of azo dyes from other azo compounds by introducing hydrocarbon radicals or substituted hydrocarbon radicals on primary or secondary amino groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3608—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered heterocyclic ring with only one nitrogen as heteroatom
- C09B29/3613—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered heterocyclic ring with only one nitrogen as heteroatom from an indole
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/02—Preparation of azo dyes from other azo compounds by sulfonation
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2430682A DE2430682A1 (de) | 1974-06-26 | 1974-06-26 | Indolyl-mono-azofarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH625540A5 true CH625540A5 (fr) | 1981-09-30 |
Family
ID=5919011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH449477A CH625540A5 (fr) | 1974-06-26 | 1975-06-24 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4060521A (fr) |
| JP (1) | JPS5118740A (fr) |
| BE (1) | BE830610A (fr) |
| CH (1) | CH625540A5 (fr) |
| DE (1) | DE2430682A1 (fr) |
| FR (1) | FR2276354A1 (fr) |
| GB (1) | GB1461058A (fr) |
| IT (1) | IT1039381B (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2527712A1 (de) * | 1975-06-21 | 1976-12-30 | Bayer Ag | Azofarbstoffe |
| JPS57129658A (en) * | 1981-02-03 | 1982-08-11 | Takashi Kitagawa | Modification of food product |
| US4954563A (en) * | 1983-03-08 | 1990-09-04 | Ciba-Geigy Corporation | Monoazo dyes containing sulfoindole coupling components |
| JPS6024156A (ja) * | 1983-07-21 | 1985-02-06 | Yamazaki Jozo Kk | 醸造品の改質法 |
| JPS60241991A (ja) * | 1984-05-16 | 1985-11-30 | Iwasaki Electric Co Ltd | 水処理装置 |
| JPS6197222A (ja) * | 1984-10-18 | 1986-05-15 | Katsumi Suzuki | 高アルカリ飲料の製造方法 |
| TW270114B (fr) * | 1993-10-22 | 1996-02-11 | Hoffmann La Roche |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1444576A1 (de) * | 1962-06-22 | 1969-10-02 | Basf Ag | Verfahren zur Herstellung wasserloeslicher Azofarbstoffe |
| BE791995A (fr) * | 1971-12-02 | 1973-05-28 | Bayer Ag | Colorants mono-azoiques |
| DE2203460C3 (de) | 1972-01-26 | 1980-08-28 | Bayer Ag, 5090 Leverkusen | Monoazofarbstoffe und Verfahren zum Färben und Bedrucken |
-
1974
- 1974-06-26 DE DE2430682A patent/DE2430682A1/de not_active Withdrawn
-
1975
- 1975-05-20 GB GB2151875A patent/GB1461058A/en not_active Expired
- 1975-06-17 US US05/587,656 patent/US4060521A/en not_active Expired - Lifetime
- 1975-06-24 IT IT24733/75A patent/IT1039381B/it active
- 1975-06-24 CH CH449477A patent/CH625540A5/de not_active IP Right Cessation
- 1975-06-24 JP JP50077054A patent/JPS5118740A/ja active Pending
- 1975-06-25 BE BE157652A patent/BE830610A/fr unknown
- 1975-06-26 FR FR7520111A patent/FR2276354A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2430682A1 (de) | 1976-01-15 |
| US4060521A (en) | 1977-11-29 |
| FR2276354A1 (fr) | 1976-01-23 |
| JPS5118740A (en) | 1976-02-14 |
| GB1461058A (en) | 1977-01-13 |
| IT1039381B (it) | 1979-12-10 |
| BE830610A (fr) | 1975-12-29 |
| FR2276354B1 (fr) | 1979-03-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |