DE2223024A1 - Monoazofarbstoffe - Google Patents
MonoazofarbstoffeInfo
- Publication number
- DE2223024A1 DE2223024A1 DE19722223024 DE2223024A DE2223024A1 DE 2223024 A1 DE2223024 A1 DE 2223024A1 DE 19722223024 DE19722223024 DE 19722223024 DE 2223024 A DE2223024 A DE 2223024A DE 2223024 A1 DE2223024 A1 DE 2223024A1
- Authority
- DE
- Germany
- Prior art keywords
- indole
- sulfonic acid
- phenyl
- methyl
- sulfone
- 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 37
- 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 8
- 239000002253 acid Substances 0.000 claims description 55
- 239000000460 chlorine Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 239000004952 Polyamide Substances 0.000 claims description 12
- 229920002647 polyamide Polymers 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 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
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 239000000835 fiber Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 238000004043 dyeing Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000012209 synthetic fiber Substances 0.000 claims description 4
- 229920002994 synthetic fiber Polymers 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 150000002475 indoles Chemical class 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 239000002657 fibrous material Substances 0.000 claims 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 42
- 150000003457 sulfones Chemical class 0.000 description 34
- -1 alkyl radicals Chemical class 0.000 description 30
- IOCXECKVGHWRNH-UHFFFAOYSA-N 2-phenylindole-2-sulfonic acid Chemical compound C1=C2C=CC=CC2=NC1(S(=O)(=O)O)C1=CC=CC=C1 IOCXECKVGHWRNH-UHFFFAOYSA-N 0.000 description 21
- 230000008878 coupling Effects 0.000 description 19
- 238000010168 coupling process Methods 0.000 description 19
- 238000005859 coupling reaction Methods 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- GXEYPKQBIPORIC-UHFFFAOYSA-N CN1C(CC2=CC=CC=C12)(S(=O)(=O)O)C1=CC=CC=C1.C1(=CC=CC=C1)C1(N=C2C=CC=CC2=C1)S(=O)(=O)O Chemical compound CN1C(CC2=CC=CC=C12)(S(=O)(=O)O)C1=CC=CC=C1.C1(=CC=CC=C1)C1(N=C2C=CC=CC2=C1)S(=O)(=O)O GXEYPKQBIPORIC-UHFFFAOYSA-N 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- FBAHVZWJNBKAAX-UHFFFAOYSA-N 1-methyl-2-phenyl-3h-indole-2-sulfonic acid Chemical compound CN1C2=CC=CC=C2CC1(S(O)(=O)=O)C1=CC=CC=C1 FBAHVZWJNBKAAX-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- MXALRLXMXCYNGF-UHFFFAOYSA-N 1h-indole-2-sulfonic acid Chemical class C1=CC=C2NC(S(=O)(=O)O)=CC2=C1 MXALRLXMXCYNGF-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- XDFUZHYOVGFDIE-UHFFFAOYSA-N 1,2,5-trimethyl-3h-indole-2-sulfonic acid Chemical compound C1=C(C)C=C2CC(S(O)(=O)=O)(C)N(C)C2=C1 XDFUZHYOVGFDIE-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003455 sulfinic acids Chemical class 0.000 description 2
- YLLOPXKVCCEOLY-UHFFFAOYSA-N 1,2-dimethyl-3h-indole-2-sulfonic acid Chemical compound C1=CC=C2CC(S(O)(=O)=O)(C)N(C)C2=C1 YLLOPXKVCCEOLY-UHFFFAOYSA-N 0.000 description 1
- BPZVIWBAHJAUHF-UHFFFAOYSA-N 1-ethyl-2-phenyl-3h-indole-2-sulfonic acid Chemical compound CCN1C2=CC=CC=C2CC1(S(O)(=O)=O)C1=CC=CC=C1 BPZVIWBAHJAUHF-UHFFFAOYSA-N 0.000 description 1
- LCSFMUUKLRKBGA-UHFFFAOYSA-N 1h-indole-5-sulfonic acid Chemical class OS(=O)(=O)C1=CC=C2NC=CC2=C1 LCSFMUUKLRKBGA-UHFFFAOYSA-N 0.000 description 1
- TZNPTXDDLRDAOY-UHFFFAOYSA-N 2,4-dichloro-6-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1N TZNPTXDDLRDAOY-UHFFFAOYSA-N 0.000 description 1
- YCWJYPIPQNETGJ-UHFFFAOYSA-N 2,5-dichloro-4-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC(Cl)=C(N)C=C1Cl YCWJYPIPQNETGJ-UHFFFAOYSA-N 0.000 description 1
- NBTLQRZVKBAEJQ-UHFFFAOYSA-N 2,5-dimethylindole-2-sulfonic acid Chemical compound C1=C(C)C=CC2=NC(C)(S(O)(=O)=O)C=C21 NBTLQRZVKBAEJQ-UHFFFAOYSA-N 0.000 description 1
- ASASRSMRAPYLQI-UHFFFAOYSA-N 2-(3-aminophenyl)sulfonylethanol Chemical compound NC1=CC=CC(S(=O)(=O)CCO)=C1 ASASRSMRAPYLQI-UHFFFAOYSA-N 0.000 description 1
- BZKULEPZXDVWPQ-UHFFFAOYSA-N 2-bromo-4-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=C(N)C(Br)=C1 BZKULEPZXDVWPQ-UHFFFAOYSA-N 0.000 description 1
- JPZWHGFZYGEABQ-UHFFFAOYSA-N 2-butylsulfonylaniline Chemical compound CCCCS(=O)(=O)C1=CC=CC=C1N JPZWHGFZYGEABQ-UHFFFAOYSA-N 0.000 description 1
- CMCMVCZKFOZIMT-UHFFFAOYSA-N 2-chloro-4-methylsulfonyl-5-(trifluoromethyl)aniline Chemical compound CS(=O)(=O)C1=C(C=C(C(=C1)Cl)N)C(F)(F)F CMCMVCZKFOZIMT-UHFFFAOYSA-N 0.000 description 1
- ZVCBXBFQEFJAOQ-UHFFFAOYSA-N 2-chloro-4-propylsulfonylaniline Chemical compound CCCS(=O)(=O)C1=CC=C(N)C(Cl)=C1 ZVCBXBFQEFJAOQ-UHFFFAOYSA-N 0.000 description 1
- JZYXWKXXTIMVOA-UHFFFAOYSA-N 2-chloro-5-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=C(Cl)C(N)=C1 JZYXWKXXTIMVOA-UHFFFAOYSA-N 0.000 description 1
- GUZUWSRUQYJVBV-UHFFFAOYSA-N 2-chloro-5-propylsulfonylaniline Chemical compound C(CC)S(=O)(=O)C1=CC(=C(C=C1)Cl)N GUZUWSRUQYJVBV-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- PWBITOSKFFPHFR-UHFFFAOYSA-N 2-ethyl-1-methyl-3H-indole-2-sulfonic acid Chemical compound CN1C(CC2=CC=CC=C12)(S(=O)(=O)O)CC PWBITOSKFFPHFR-UHFFFAOYSA-N 0.000 description 1
- HFQXJCLUOBJBMV-UHFFFAOYSA-N 2-ethylindole-2-sulfonic acid Chemical compound C1=CC=CC2=NC(CC)(S(O)(=O)=O)C=C21 HFQXJCLUOBJBMV-UHFFFAOYSA-N 0.000 description 1
- SIIUERHMYOPFQH-UHFFFAOYSA-N 2-ethylsulfonylaniline Chemical compound CCS(=O)(=O)C1=CC=CC=C1N SIIUERHMYOPFQH-UHFFFAOYSA-N 0.000 description 1
- UGUIBNHHDIEZJI-UHFFFAOYSA-N 2-fluoro-4-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=C(N)C(F)=C1 UGUIBNHHDIEZJI-UHFFFAOYSA-N 0.000 description 1
- FBZRMLLLOMNOLJ-UHFFFAOYSA-N 2-methoxy-4-methylsulfonylaniline Chemical compound COC1=CC(S(C)(=O)=O)=CC=C1N FBZRMLLLOMNOLJ-UHFFFAOYSA-N 0.000 description 1
- DWQJEYKNLZWXLJ-UHFFFAOYSA-N 2-methyl-4-methylsulfonylaniline Chemical compound CC1=CC(S(C)(=O)=O)=CC=C1N DWQJEYKNLZWXLJ-UHFFFAOYSA-N 0.000 description 1
- AUSRSVRJOXYXMI-UHFFFAOYSA-N 2-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=CC=C1N AUSRSVRJOXYXMI-UHFFFAOYSA-N 0.000 description 1
- DEQVKVCODPHASQ-UHFFFAOYSA-N 2-propylsulfonylaniline Chemical compound CCCS(=O)(=O)C1=CC=CC=C1N DEQVKVCODPHASQ-UHFFFAOYSA-N 0.000 description 1
- MNCVDLWYPKJXKR-UHFFFAOYSA-N 3-benzylsulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)CC=2C=CC=CC=2)=C1 MNCVDLWYPKJXKR-UHFFFAOYSA-N 0.000 description 1
- AAQPOJXXWZKHNL-UHFFFAOYSA-N 3-butylsulfonylaniline Chemical compound CCCCS(=O)(=O)C1=CC=CC(N)=C1 AAQPOJXXWZKHNL-UHFFFAOYSA-N 0.000 description 1
- ZCIQLGLOYPISKI-UHFFFAOYSA-N 3-ethylsulfonylaniline Chemical compound CCS(=O)(=O)C1=CC=CC(N)=C1 ZCIQLGLOYPISKI-UHFFFAOYSA-N 0.000 description 1
- MBNPJRQKQLLRIS-UHFFFAOYSA-N 3-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=CC(N)=C1 MBNPJRQKQLLRIS-UHFFFAOYSA-N 0.000 description 1
- DTDMZVNYIPBTQP-UHFFFAOYSA-N 4,5-dichloro-2-ethylsulfonylaniline Chemical compound CCS(=O)(=O)C1=CC(Cl)=C(Cl)C=C1N DTDMZVNYIPBTQP-UHFFFAOYSA-N 0.000 description 1
- QLBPZTOZFWUFON-UHFFFAOYSA-N 4,5-dichloro-2-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC(Cl)=C(Cl)C=C1N QLBPZTOZFWUFON-UHFFFAOYSA-N 0.000 description 1
- NKKBPGJRGCEQMP-UHFFFAOYSA-N 4-(4-amino-3,5-dichlorophenyl)sulfonyl-2,6-dichloroaniline Chemical compound C1=C(Cl)C(N)=C(Cl)C=C1S(=O)(=O)C1=CC(Cl)=C(N)C(Cl)=C1 NKKBPGJRGCEQMP-UHFFFAOYSA-N 0.000 description 1
- GIGMLNZJHRMMSR-UHFFFAOYSA-N 4-[(4-chlorophenyl)methylsulfonyl]-2-(trifluoromethyl)aniline Chemical compound FC(C=1C=C(C=CC=1N)S(=O)(=O)CC1=CC=C(C=C1)Cl)(F)F GIGMLNZJHRMMSR-UHFFFAOYSA-N 0.000 description 1
- KRAXRCRORAUEGY-UHFFFAOYSA-N 4-[4-amino-3-(trifluoromethyl)phenyl]sulfonyl-2-(trifluoromethyl)aniline Chemical compound C1=C(C(F)(F)F)C(N)=CC=C1S(=O)(=O)C1=CC=C(N)C(C(F)(F)F)=C1 KRAXRCRORAUEGY-UHFFFAOYSA-N 0.000 description 1
- BWLCYWANLBVZRG-UHFFFAOYSA-N 4-butylsulfonyl-2-(trifluoromethyl)aniline Chemical compound CCCCS(=O)(=O)C1=CC(=C(N)C=C1)C(F)(F)F BWLCYWANLBVZRG-UHFFFAOYSA-N 0.000 description 1
- IUBRKPPRFZDYDU-UHFFFAOYSA-N 4-butylsulfonyl-2-chloroaniline Chemical compound CCCCS(=O)(=O)C1=CC=C(N)C(Cl)=C1 IUBRKPPRFZDYDU-UHFFFAOYSA-N 0.000 description 1
- STHUWFMGWGXCNC-UHFFFAOYSA-N 4-chloro-3-propylsulfonylaniline Chemical compound CCCS(=O)(=O)C1=CC(N)=CC=C1Cl STHUWFMGWGXCNC-UHFFFAOYSA-N 0.000 description 1
- NXTSLDNXEFOTSB-UHFFFAOYSA-N 4-ethylsulfonyl-2-methylaniline Chemical compound CCS(=O)(=O)C1=CC=C(N)C(C)=C1 NXTSLDNXEFOTSB-UHFFFAOYSA-N 0.000 description 1
- CBJKYWQOFCTMLG-UHFFFAOYSA-N 4-ethylsulfonylaniline Chemical compound CCS(=O)(=O)C1=CC=C(N)C=C1 CBJKYWQOFCTMLG-UHFFFAOYSA-N 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- NIDLKNAWADHJIZ-UHFFFAOYSA-N 4-methylsulfonyl-2,5-bis(trifluoromethyl)aniline Chemical compound CS(=O)(=O)C1=C(C=C(C(=C1)C(F)(F)F)N)C(F)(F)F NIDLKNAWADHJIZ-UHFFFAOYSA-N 0.000 description 1
- PUGQEBSNSODOMY-UHFFFAOYSA-N 4-methylsulfonyl-2-(trifluoromethyl)aniline Chemical compound CS(=O)(=O)C1=CC=C(N)C(C(F)(F)F)=C1 PUGQEBSNSODOMY-UHFFFAOYSA-N 0.000 description 1
- XJEVFFNOMKXBLU-UHFFFAOYSA-N 4-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=C(N)C=C1 XJEVFFNOMKXBLU-UHFFFAOYSA-N 0.000 description 1
- FCIYMEGIZPWNNO-UHFFFAOYSA-N 5-butylsulfonyl-2-(trifluoromethyl)aniline Chemical compound C(CCC)S(=O)(=O)C1=CC(=C(C=C1)C(F)(F)F)N FCIYMEGIZPWNNO-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
- NQMRSKWASDTQLD-UHFFFAOYSA-N C(C1=CC=CC=C1)S(=O)(=O)C1=CC(=C(C=C1)N)C(F)(F)F Chemical compound C(C1=CC=CC=C1)S(=O)(=O)C1=CC(=C(C=C1)N)C(F)(F)F NQMRSKWASDTQLD-UHFFFAOYSA-N 0.000 description 1
- KQCZLBFOBONNMP-UHFFFAOYSA-N C(CC1=CC=CC=C1)S(=O)(=O)C1=C(C=C(C(=C1)Cl)N)Cl Chemical compound C(CC1=CC=CC=C1)S(=O)(=O)C1=C(C=C(C(=C1)Cl)N)Cl KQCZLBFOBONNMP-UHFFFAOYSA-N 0.000 description 1
- QDDBIAZUTMZVSK-UHFFFAOYSA-N CC1(C=C2C=C(C=CC2=N1)Cl)S(=O)(=O)O Chemical compound CC1(C=C2C=C(C=CC2=N1)Cl)S(=O)(=O)O QDDBIAZUTMZVSK-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
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
- 229910014142 Na—O Inorganic materials 0.000 description 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical group O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 239000000980 acid dye Substances 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
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002152 aqueous-organic solution Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 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
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- OHZSKBRLHKTRMZ-UHFFFAOYSA-N indole-1-sulfonic acid Chemical compound C1=CC=C2N(S(=O)(=O)O)C=CC2=C1 OHZSKBRLHKTRMZ-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003960 organic solvent Substances 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
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000000926 separation method Methods 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
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 239000001043 yellow dye Substances 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
- C09B62/503—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 an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/507—Azo dyes
- C09B62/51—Monoazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722223024 DE2223024A1 (de) | 1972-05-10 | 1972-05-10 | Monoazofarbstoffe |
| NL7306353A NL7306353A (enrdf_load_stackoverflow) | 1972-05-10 | 1973-05-07 | |
| CH652573D CH652573A4 (enrdf_load_stackoverflow) | 1972-05-10 | 1973-05-08 | |
| IT2384773A IT987213B (it) | 1972-05-10 | 1973-05-08 | Coloranti monoazoici |
| CH1254774A CH557404A (de) | 1972-05-10 | 1973-05-08 | Verfahren zur herstellung von monoazofarbstoffen. |
| CH652573A CH560795A (enrdf_load_stackoverflow) | 1972-05-10 | 1973-05-08 | |
| JP5034973A JPS4948722A (enrdf_load_stackoverflow) | 1972-05-10 | 1973-05-08 | |
| GB2214073A GB1384508A (en) | 1972-05-10 | 1973-05-09 | Monoazo dyestuffs of the phenylazoindole series |
| BE130910A BE799296A (fr) | 1972-05-10 | 1973-05-09 | Colorants monoazoiques, |
| FR7316891A FR2184058B1 (enrdf_load_stackoverflow) | 1972-05-10 | 1973-05-10 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722223024 DE2223024A1 (de) | 1972-05-10 | 1972-05-10 | Monoazofarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2223024A1 true DE2223024A1 (de) | 1973-11-29 |
Family
ID=5844632
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722223024 Pending DE2223024A1 (de) | 1972-05-10 | 1972-05-10 | Monoazofarbstoffe |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4948722A (enrdf_load_stackoverflow) |
| BE (1) | BE799296A (enrdf_load_stackoverflow) |
| CH (3) | CH652573A4 (enrdf_load_stackoverflow) |
| DE (1) | DE2223024A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2184058B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1384508A (enrdf_load_stackoverflow) |
| IT (1) | IT987213B (enrdf_load_stackoverflow) |
| NL (1) | NL7306353A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4954563A (en) * | 1983-03-08 | 1990-09-04 | Ciba-Geigy Corporation | Monoazo dyes containing sulfoindole coupling components |
-
1972
- 1972-05-10 DE DE19722223024 patent/DE2223024A1/de active Pending
-
1973
- 1973-05-07 NL NL7306353A patent/NL7306353A/xx unknown
- 1973-05-08 CH CH652573D patent/CH652573A4/xx unknown
- 1973-05-08 IT IT2384773A patent/IT987213B/it active
- 1973-05-08 JP JP5034973A patent/JPS4948722A/ja active Pending
- 1973-05-08 CH CH1254774A patent/CH557404A/xx not_active IP Right Cessation
- 1973-05-08 CH CH652573A patent/CH560795A/xx not_active IP Right Cessation
- 1973-05-09 BE BE130910A patent/BE799296A/xx unknown
- 1973-05-09 GB GB2214073A patent/GB1384508A/en not_active Expired
- 1973-05-10 FR FR7316891A patent/FR2184058B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4948722A (enrdf_load_stackoverflow) | 1974-05-11 |
| FR2184058B1 (enrdf_load_stackoverflow) | 1977-02-11 |
| GB1384508A (en) | 1975-02-19 |
| NL7306353A (enrdf_load_stackoverflow) | 1973-11-13 |
| CH652573A4 (enrdf_load_stackoverflow) | 1974-10-15 |
| FR2184058A1 (enrdf_load_stackoverflow) | 1973-12-21 |
| BE799296A (fr) | 1973-11-09 |
| CH560795A (enrdf_load_stackoverflow) | 1975-04-15 |
| CH557404A (de) | 1974-12-31 |
| IT987213B (it) | 1975-02-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |