DE2425812A1 - Sulfogruppenhaltige monoazofarbstoffe - Google Patents
Sulfogruppenhaltige monoazofarbstoffeInfo
- Publication number
- DE2425812A1 DE2425812A1 DE19742425812 DE2425812A DE2425812A1 DE 2425812 A1 DE2425812 A1 DE 2425812A1 DE 19742425812 DE19742425812 DE 19742425812 DE 2425812 A DE2425812 A DE 2425812A DE 2425812 A1 DE2425812 A1 DE 2425812A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- indole
- carbon atoms
- amino
- groups
- 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.)
- Pending
Links
- 239000000975 dye Substances 0.000 title claims description 50
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical compound [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 title claims description 13
- -1 hydroxyethoxy Chemical group 0.000 claims description 64
- 125000004432 carbon atom Chemical group C* 0.000 claims description 63
- 239000002253 acid Substances 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 17
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 150000002431 hydrogen Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 238000004043 dyeing Methods 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- APKZPKINPXTSNL-UHFFFAOYSA-N 1,3,4-oxadiazol-2-amine Chemical compound NC1=NN=CO1 APKZPKINPXTSNL-UHFFFAOYSA-N 0.000 claims description 4
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 239000012209 synthetic fiber Substances 0.000 claims description 4
- 229920002994 synthetic fiber Polymers 0.000 claims description 4
- 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 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 150000002475 indoles Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 47
- 229920002647 polyamide Polymers 0.000 description 25
- 239000004952 Polyamide Substances 0.000 description 24
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 24
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 24
- 230000008878 coupling Effects 0.000 description 22
- 238000010168 coupling process Methods 0.000 description 22
- 238000005859 coupling reaction Methods 0.000 description 22
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 17
- 206010039587 Scarlet Fever Diseases 0.000 description 15
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 14
- IZNVWIXUMIMNSP-UHFFFAOYSA-N 2-phenyl-1h-indole-5-sulfonic acid Chemical compound C=1C2=CC(S(=O)(=O)O)=CC=C2NC=1C1=CC=CC=C1 IZNVWIXUMIMNSP-UHFFFAOYSA-N 0.000 description 12
- LCSFMUUKLRKBGA-UHFFFAOYSA-N 1h-indole-5-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2NC=CC2=C1 LCSFMUUKLRKBGA-UHFFFAOYSA-N 0.000 description 11
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 11
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- ORHGXZPRRIKWCS-UHFFFAOYSA-N 4-(1h-indol-2-yl)benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1C1=CC2=CC=CC=C2N1 ORHGXZPRRIKWCS-UHFFFAOYSA-N 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VJHTZTZXOKVQRN-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine Chemical compound NC1=NC=NS1 VJHTZTZXOKVQRN-UHFFFAOYSA-N 0.000 description 3
- WIIICVCDFYLYTQ-UHFFFAOYSA-N 1-sulfonyl-1,3-benzothiazole Chemical compound C1=CC=C2S(=S(=O)=O)C=NC2=C1 WIIICVCDFYLYTQ-UHFFFAOYSA-N 0.000 description 3
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 3
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 3
- GGDKHYGXGDUGSX-UHFFFAOYSA-N C1(=CC=CC=C1)C=1NC2=C(C=CC=C2C1)S(=O)(=O)O Chemical compound C1(=CC=CC=C1)C=1NC2=C(C=CC=C2C1)S(=O)(=O)O GGDKHYGXGDUGSX-UHFFFAOYSA-N 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 description 2
- YSGYUYIEJJVBOV-UHFFFAOYSA-N 1,5-dimethyl-2-phenylindole Chemical compound C=1C2=CC(C)=CC=C2N(C)C=1C1=CC=CC=C1 YSGYUYIEJJVBOV-UHFFFAOYSA-N 0.000 description 2
- BISDQDULBWQVRY-UHFFFAOYSA-N 1-methyl-2-phenylindole-5-sulfonic acid Chemical compound C=1C2=CC(S(O)(=O)=O)=CC=C2N(C)C=1C1=CC=CC=C1 BISDQDULBWQVRY-UHFFFAOYSA-N 0.000 description 2
- JSKJAICVFPRVHJ-UHFFFAOYSA-N 2,1-benzothiazol-3-amine Chemical compound C1=CC=CC2=C(N)SN=C21 JSKJAICVFPRVHJ-UHFFFAOYSA-N 0.000 description 2
- LSDMJJMOTHKCRA-UHFFFAOYSA-N 2-(2-phenylphenyl)-1h-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1C1=CC=CC=C1 LSDMJJMOTHKCRA-UHFFFAOYSA-N 0.000 description 2
- PXUHDKHWMHTOIU-UHFFFAOYSA-N 2-phenyl-1H-indole-6-sulfonic acid Chemical compound C1(=CC=CC=C1)C=1NC2=CC(=CC=C2C1)S(=O)(=O)O PXUHDKHWMHTOIU-UHFFFAOYSA-N 0.000 description 2
- OEQQFQXMCPMEIH-UHFFFAOYSA-N 4-chloro-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2SC(N)=NC2=C1Cl OEQQFQXMCPMEIH-UHFFFAOYSA-N 0.000 description 2
- GHKHTBMTSUEBJD-UHFFFAOYSA-N 5,6-dichloro-1,3-benzothiazol-2-amine Chemical compound ClC1=C(Cl)C=C2SC(N)=NC2=C1 GHKHTBMTSUEBJD-UHFFFAOYSA-N 0.000 description 2
- BKBGECFJQWIQBW-UHFFFAOYSA-N 5,7-dibromo-2,1-benzothiazol-3-amine Chemical compound BrC1=CC(Br)=CC2=C(N)SN=C21 BKBGECFJQWIQBW-UHFFFAOYSA-N 0.000 description 2
- JPFTUUXPCFNLIX-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-indole Chemical compound C=1C2=CC(C)=CC=C2NC=1C1=CC=CC=C1 JPFTUUXPCFNLIX-UHFFFAOYSA-N 0.000 description 2
- VZEBSJIOUMDNLY-UHFFFAOYSA-N 6-bromo-1,3-benzothiazol-2-amine Chemical compound C1=C(Br)C=C2SC(N)=NC2=C1 VZEBSJIOUMDNLY-UHFFFAOYSA-N 0.000 description 2
- HQULYFAKUZDRPB-UHFFFAOYSA-N 6-bromo-2-[4-(trifluoromethoxy)phenoxy]-1,3-benzothiazole Chemical compound BrC1=CC2=C(N=C(S2)OC2=CC=C(C=C2)OC(F)(F)F)C=C1 HQULYFAKUZDRPB-UHFFFAOYSA-N 0.000 description 2
- UZJMSFZHPMSAHI-UHFFFAOYSA-N 6-butoxy-1,3-benzothiazol-2-amine Chemical compound CCCCOC1=CC=C2N=C(N)SC2=C1 UZJMSFZHPMSAHI-UHFFFAOYSA-N 0.000 description 2
- VMNXKIDUTPOHPO-UHFFFAOYSA-N 6-chloro-1,3-benzothiazol-2-amine Chemical compound C1=C(Cl)C=C2SC(N)=NC2=C1 VMNXKIDUTPOHPO-UHFFFAOYSA-N 0.000 description 2
- KOYJWFGMEBETBU-UHFFFAOYSA-N 6-ethoxy-1,3-benzothiazol-2-amine Chemical compound CCOC1=CC=C2N=C(N)SC2=C1 KOYJWFGMEBETBU-UHFFFAOYSA-N 0.000 description 2
- KZHGPDSVHSDCMX-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2N=C(N)SC2=C1 KZHGPDSVHSDCMX-UHFFFAOYSA-N 0.000 description 2
- ZYHNHJAMVNINSY-UHFFFAOYSA-N 6-methylsulfonyl-1,3-benzothiazol-2-amine Chemical compound CS(=O)(=O)C1=CC=C2N=C(N)SC2=C1 ZYHNHJAMVNINSY-UHFFFAOYSA-N 0.000 description 2
- GPNAVOJCQIEKQF-UHFFFAOYSA-N 6-nitro-1,3-benzothiazol-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N)=NC2=C1 GPNAVOJCQIEKQF-UHFFFAOYSA-N 0.000 description 2
- GIOCFNWQTZDWNE-UHFFFAOYSA-N 6-phenyl-1,3-benzothiazol-2-amine Chemical compound C1=C2SC(N)=NC2=CC=C1C1=CC=CC=C1 GIOCFNWQTZDWNE-UHFFFAOYSA-N 0.000 description 2
- UIQWUDYNLQPCDA-UHFFFAOYSA-N C1=CC=C2S(=C=O)C=NC2=C1 Chemical group C1=CC=C2S(=C=O)C=NC2=C1 UIQWUDYNLQPCDA-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000980 acid dye Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000001000 anthraquinone dye Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- IENWWEQWDWFQKN-UHFFFAOYSA-N (2-amino-1,3-benzothiazol-6-yl) benzenesulfonate Chemical compound C1=C2SC(N)=NC2=CC=C1OS(=O)(=O)C1=CC=CC=C1 IENWWEQWDWFQKN-UHFFFAOYSA-N 0.000 description 1
- ITRPVCCHEPKDQO-UHFFFAOYSA-N (2-amino-1,3-benzothiazol-6-yl) ethanesulfonate Chemical compound CCS(=O)(=O)OC1=CC=C2N=C(N)SC2=C1 ITRPVCCHEPKDQO-UHFFFAOYSA-N 0.000 description 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
- CIYLMZGSYVJWGH-UHFFFAOYSA-N 1-(2-phenylindol-1-yl)butan-2-yl acetate Chemical compound C=1C2=CC=CC=C2N(CC(CC)OC(C)=O)C=1C1=CC=CC=C1 CIYLMZGSYVJWGH-UHFFFAOYSA-N 0.000 description 1
- ZMAKCUFUVDVSMR-UHFFFAOYSA-N 1-(2-phenylindol-1-yl)propan-2-yl acetate Chemical compound C=1C2=CC=CC=C2N(CC(C)OC(C)=O)C=1C1=CC=CC=C1 ZMAKCUFUVDVSMR-UHFFFAOYSA-N 0.000 description 1
- BJKHSCZLCDFKJV-UHFFFAOYSA-N 1-(2-phenylindol-1-yl)propan-2-yl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC(C)CN(C1=CC=CC=C1C=1)C=1C1=CC=CC=C1 BJKHSCZLCDFKJV-UHFFFAOYSA-N 0.000 description 1
- SLVLCEXJDAGNCL-UHFFFAOYSA-N 1-(5-bromo-2-phenylindol-1-yl)propan-2-ol Chemical compound C=1C2=CC(Br)=CC=C2N(CC(O)C)C=1C1=CC=CC=C1 SLVLCEXJDAGNCL-UHFFFAOYSA-N 0.000 description 1
- GSNVFMLKTIBCGQ-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)indol-1-yl]butan-2-ol Chemical compound C=1C2=CC=CC=C2N(CC(O)CC)C=1C1=CC=C(Cl)C=C1 GSNVFMLKTIBCGQ-UHFFFAOYSA-N 0.000 description 1
- NTEREHKLCGIVKK-UHFFFAOYSA-N 1-benzyl-2-phenylindole Chemical compound C=1C=CC=CC=1C1=CC2=CC=CC=C2N1CC1=CC=CC=C1 NTEREHKLCGIVKK-UHFFFAOYSA-N 0.000 description 1
- RAKSXVONTIQCGY-UHFFFAOYSA-N 1-ethyl-2-phenylindole Chemical compound C=1C2=CC=CC=C2N(CC)C=1C1=CC=CC=C1 RAKSXVONTIQCGY-UHFFFAOYSA-N 0.000 description 1
- SFWZZSXCWQTORH-UHFFFAOYSA-N 1-methyl-2-phenylindole Chemical compound C=1C2=CC=CC=C2N(C)C=1C1=CC=CC=C1 SFWZZSXCWQTORH-UHFFFAOYSA-N 0.000 description 1
- HOWVVSWFUMLIMA-UHFFFAOYSA-N 1-methyl-7-nitro-2-phenylindole Chemical compound C=1C2=CC=CC([N+]([O-])=O)=C2N(C)C=1C1=CC=CC=C1 HOWVVSWFUMLIMA-UHFFFAOYSA-N 0.000 description 1
- LWFHXMXXTQLMTH-UHFFFAOYSA-N 1-phenoxy-3-(2-phenylindol-1-yl)propan-2-ol Chemical compound C=1C=CC=CC=1C1=CC2=CC=CC=C2N1CC(O)COC1=CC=CC=C1 LWFHXMXXTQLMTH-UHFFFAOYSA-N 0.000 description 1
- WRBMSRKAUBTBMA-UHFFFAOYSA-N 1h-indole-4-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=C1C=CN2 WRBMSRKAUBTBMA-UHFFFAOYSA-N 0.000 description 1
- PBYLZDGPBMZOSA-UHFFFAOYSA-N 1h-indole-7-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=C1NC=C2 PBYLZDGPBMZOSA-UHFFFAOYSA-N 0.000 description 1
- JGQPSDIWMGNAPE-UHFFFAOYSA-N 2,1-benzothiazole Chemical compound C1=CC=CC2=CSN=C21 JGQPSDIWMGNAPE-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
- CKHBIJHJQRGGKL-UHFFFAOYSA-N 2-(2-phenylindol-1-yl)butan-1-ol Chemical compound C=1C2=CC=CC=C2N(C(CO)CC)C=1C1=CC=CC=C1 CKHBIJHJQRGGKL-UHFFFAOYSA-N 0.000 description 1
- NRCYUECEMCNXGN-UHFFFAOYSA-N 2-(2-phenylindol-1-yl)propan-1-ol Chemical compound C=1C2=CC=CC=C2N(C(CO)C)C=1C1=CC=CC=C1 NRCYUECEMCNXGN-UHFFFAOYSA-N 0.000 description 1
- BWEPILBIWVZIPA-UHFFFAOYSA-N 2-(4-bromophenyl)-1h-indole Chemical compound C1=CC(Br)=CC=C1C1=CC2=CC=CC=C2N1 BWEPILBIWVZIPA-UHFFFAOYSA-N 0.000 description 1
- KDNXKQSAAZNUCK-UHFFFAOYSA-N 2-(4-chlorophenyl)-1h-indole Chemical compound C1=CC(Cl)=CC=C1C1=CC2=CC=CC=C2N1 KDNXKQSAAZNUCK-UHFFFAOYSA-N 0.000 description 1
- BHCBPEBRFMLOND-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1h-indole Chemical compound C1=CC(OC)=CC=C1C1=CC2=CC=CC=C2N1 BHCBPEBRFMLOND-UHFFFAOYSA-N 0.000 description 1
- VPXGIHGJJJBJFP-UHFFFAOYSA-N 2-(4-methylphenyl)-1h-indole Chemical compound C1=CC(C)=CC=C1C1=CC2=CC=CC=C2N1 VPXGIHGJJJBJFP-UHFFFAOYSA-N 0.000 description 1
- IMEOASMPBMUXOO-UHFFFAOYSA-N 2-[(2-amino-1,3-benzothiazol-6-yl)oxy]ethanol Chemical compound C1=C(OCCO)C=C2SC(N)=NC2=C1 IMEOASMPBMUXOO-UHFFFAOYSA-N 0.000 description 1
- VKVXZWPNTANEER-UHFFFAOYSA-N 2-[(2-amino-1,3-benzothiazol-6-yl)sulfanyl]ethanol Chemical compound C1=C(SCCO)C=C2SC(N)=NC2=C1 VKVXZWPNTANEER-UHFFFAOYSA-N 0.000 description 1
- GDFCZZHSWGWCHP-UHFFFAOYSA-N 2-amino-1,3-benzothiazole-6-carbonitrile Chemical compound C1=C(C#N)C=C2SC(N)=NC2=C1 GDFCZZHSWGWCHP-UHFFFAOYSA-N 0.000 description 1
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- UHZHEOAEJRHUBW-UHFFFAOYSA-N 5-phenyl-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1=CC=CC=C1 UHZHEOAEJRHUBW-UHFFFAOYSA-N 0.000 description 1
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- JNYLMODTPLSLIF-UHFFFAOYSA-N 6-(trifluoromethyl)pyridine-3-carboxylic acid Chemical group OC(=O)C1=CC=C(C(F)(F)F)N=C1 JNYLMODTPLSLIF-UHFFFAOYSA-N 0.000 description 1
- CBWVYWQALBPLIV-UHFFFAOYSA-N 6-chloro-1-methyl-2-phenylindole Chemical compound C=1C2=CC=C(Cl)C=C2N(C)C=1C1=CC=CC=C1 CBWVYWQALBPLIV-UHFFFAOYSA-N 0.000 description 1
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- QZDLVNZODBWSBN-UHFFFAOYSA-N 7-chloro-1-methyl-2-phenylindole Chemical compound C=1C2=CC=CC(Cl)=C2N(C)C=1C1=CC=CC=C1 QZDLVNZODBWSBN-UHFFFAOYSA-N 0.000 description 1
- RLVLGCBQDWHTEV-UHFFFAOYSA-N 7-ethyl-1-methyl-2-phenylindole Chemical compound CN1C=2C(CC)=CC=CC=2C=C1C1=CC=CC=C1 RLVLGCBQDWHTEV-UHFFFAOYSA-N 0.000 description 1
- 229930195212 Fischerindole Natural products 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
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- 229920002292 Nylon 6 Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- KBYMQDYGNRTQBR-UHFFFAOYSA-N [S-][N+]=O Chemical compound [S-][N+]=O KBYMQDYGNRTQBR-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- YJVBLROMQZEFPA-UHFFFAOYSA-L acid red 26 Chemical compound [Na+].[Na+].CC1=CC(C)=CC=C1N=NC1=C(O)C(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=CC=C12 YJVBLROMQZEFPA-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- BITVLCPCCBVIQU-UHFFFAOYSA-N butyl 2-amino-1,3-benzothiazole-6-carboxylate Chemical compound CCCCOC(=O)C1=CC=C2N=C(N)SC2=C1 BITVLCPCCBVIQU-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- GGYMYCNIILQYJQ-UHFFFAOYSA-N cyclohexyl 2-amino-1,3-benzothiazole-6-carboxylate Chemical compound C1=C2SC(N)=NC2=CC=C1C(=O)OC1CCCCC1 GGYMYCNIILQYJQ-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- LCUYJVNHTWTGJJ-UHFFFAOYSA-N ethyl 2-amino-1,3-benzothiazole-4-carboxylate Chemical compound CCOC(=O)C1=CC=CC2=C1N=C(N)S2 LCUYJVNHTWTGJJ-UHFFFAOYSA-N 0.000 description 1
- YXTDBBPBFYGJHX-UHFFFAOYSA-N ethyl 2-amino-1,3-benzothiazole-6-sulfonate Chemical compound CCOS(=O)(=O)C1=CC=C2N=C(N)SC2=C1 YXTDBBPBFYGJHX-UHFFFAOYSA-N 0.000 description 1
- DCXPUCJOLFJNDL-UHFFFAOYSA-N ethyl 2-hydroxy-3-(2-phenylindol-1-yl)propanoate Chemical compound C=1C2=CC=CC=C2N(CC(O)C(=O)OCC)C=1C1=CC=CC=C1 DCXPUCJOLFJNDL-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JWSQSUAAMGQUJI-UHFFFAOYSA-N methyl 2-amino-1,3-benzothiazole-4-carboxylate Chemical compound COC(=O)C1=CC=CC2=C1N=C(N)S2 JWSQSUAAMGQUJI-UHFFFAOYSA-N 0.000 description 1
- DNGZINUIRBDWED-UHFFFAOYSA-N methyl 2-amino-1,3-benzothiazole-6-carboxylate Chemical compound COC(=O)C1=CC=C2N=C(N)SC2=C1 DNGZINUIRBDWED-UHFFFAOYSA-N 0.000 description 1
- HXPJNTQHMNIVAX-UHFFFAOYSA-N methyl 2-amino-1,3-benzothiazole-6-sulfonate Chemical compound COS(=O)(=O)C1=CC=C2N=C(N)SC2=C1 HXPJNTQHMNIVAX-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
- NYNIVZSJRFYBJM-UHFFFAOYSA-N methyl n-[3-(2-phenylindol-1-yl)propyl]carbamate Chemical compound C=1C2=CC=CC=C2N(CCCNC(=O)OC)C=1C1=CC=CC=C1 NYNIVZSJRFYBJM-UHFFFAOYSA-N 0.000 description 1
- GCXZUIFKEQCVSZ-UHFFFAOYSA-N n-(2-amino-1,3-benzothiazol-6-yl)-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC1=CC=C(N=C(N)S2)C2=C1 GCXZUIFKEQCVSZ-UHFFFAOYSA-N 0.000 description 1
- BRSUAKMKDAAYJX-UHFFFAOYSA-N n-(2-amino-1,3-benzothiazol-6-yl)acetamide Chemical compound CC(=O)NC1=CC=C2N=C(N)SC2=C1 BRSUAKMKDAAYJX-UHFFFAOYSA-N 0.000 description 1
- FKDRWIQBZAWXLS-UHFFFAOYSA-N n-(3-amino-2,1-benzothiazol-5-yl)acetamide Chemical compound C1=C(NC(=O)C)C=CC2=NSC(N)=C21 FKDRWIQBZAWXLS-UHFFFAOYSA-N 0.000 description 1
- AQDOPVLFGPZFOW-UHFFFAOYSA-N n-[3-(2-phenylindol-1-yl)propyl]propanamide Chemical compound C=1C2=CC=CC=C2N(CCCNC(=O)CC)C=1C1=CC=CC=C1 AQDOPVLFGPZFOW-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
- UDBWZKPBBYNVBK-UHFFFAOYSA-N phenyl 2-amino-1,3-benzothiazole-6-sulfonate Chemical compound C1=C2SC(N)=NC2=CC=C1S(=O)(=O)OC1=CC=CC=C1 UDBWZKPBBYNVBK-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 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
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/443—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being alternatively specified
- C09B62/447—Azo dyes
- C09B62/45—Monoazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742425812 DE2425812A1 (de) | 1974-05-28 | 1974-05-28 | Sulfogruppenhaltige monoazofarbstoffe |
| GB1896775A GB1457231A (en) | 1974-05-28 | 1975-05-06 | Monoazo dyestuffs derived from substituted indole coupling components |
| JP6204775A JPS515334A (ja) | 1974-05-28 | 1975-05-26 | Suruhokiganjumonoazosenryonoseizohoho |
| BE156687A BE829465A (fr) | 1974-05-28 | 1975-05-26 | Colorants monoazoiques contenant des groupes acide sulfonique, et leur obtention |
| CH668275A CH603895B5 (enrdf_load_stackoverflow) | 1974-05-28 | 1975-05-26 | |
| CH668275D CH668275A4 (enrdf_load_stackoverflow) | 1974-05-28 | 1975-05-26 | |
| FR7516649A FR2273048B1 (enrdf_load_stackoverflow) | 1974-05-28 | 1975-05-28 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742425812 DE2425812A1 (de) | 1974-05-28 | 1974-05-28 | Sulfogruppenhaltige monoazofarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2425812A1 true DE2425812A1 (de) | 1975-12-18 |
Family
ID=5916685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742425812 Pending DE2425812A1 (de) | 1974-05-28 | 1974-05-28 | Sulfogruppenhaltige monoazofarbstoffe |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS515334A (enrdf_load_stackoverflow) |
| BE (1) | BE829465A (enrdf_load_stackoverflow) |
| CH (2) | CH603895B5 (enrdf_load_stackoverflow) |
| DE (1) | DE2425812A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2273048B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1457231A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2708188C2 (de) | 1977-02-25 | 1979-02-08 | Bayer Ag, 5090 Leverkusen | Stabilisierung anionischer Indolfarbstoffe |
| JPH07116551B2 (ja) * | 1986-01-30 | 1995-12-13 | 大同特殊鋼株式会社 | 浸炭用鋼 |
-
1974
- 1974-05-28 DE DE19742425812 patent/DE2425812A1/de active Pending
-
1975
- 1975-05-06 GB GB1896775A patent/GB1457231A/en not_active Expired
- 1975-05-26 BE BE156687A patent/BE829465A/xx unknown
- 1975-05-26 JP JP6204775A patent/JPS515334A/ja active Pending
- 1975-05-26 CH CH668275A patent/CH603895B5/xx not_active IP Right Cessation
- 1975-05-26 CH CH668275D patent/CH668275A4/xx unknown
- 1975-05-28 FR FR7516649A patent/FR2273048B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH603895B5 (enrdf_load_stackoverflow) | 1978-08-31 |
| JPS515334A (ja) | 1976-01-17 |
| FR2273048A1 (enrdf_load_stackoverflow) | 1975-12-26 |
| CH668275A4 (enrdf_load_stackoverflow) | 1977-08-15 |
| BE829465A (fr) | 1975-11-26 |
| FR2273048B1 (enrdf_load_stackoverflow) | 1979-03-23 |
| GB1457231A (en) | 1976-12-01 |
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| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |