GB1561420A - Azo dyestuffs containing a phthalimido - alkyl group - Google Patents
Azo dyestuffs containing a phthalimido - alkyl group Download PDFInfo
- Publication number
- GB1561420A GB1561420A GB3695077A GB3695077A GB1561420A GB 1561420 A GB1561420 A GB 1561420A GB 3695077 A GB3695077 A GB 3695077A GB 3695077 A GB3695077 A GB 3695077A GB 1561420 A GB1561420 A GB 1561420A
- Authority
- GB
- United Kingdom
- Prior art keywords
- denotes
- group
- amino
- methyl
- phenyl
- 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.)
- Expired
Links
- 125000005544 phthalimido group Chemical group 0.000 title 1
- -1 acetylamino, methoxy Chemical group 0.000 claims description 90
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 229910006069 SO3H Inorganic materials 0.000 claims description 17
- 239000000975 dye Substances 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 239000004952 Polyamide Substances 0.000 claims description 8
- 229920002647 polyamide Polymers 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 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 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 238000004043 dyeing Methods 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910004727 OSO3H Inorganic materials 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 3
- 229920002994 synthetic fiber Polymers 0.000 claims description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 2
- 229910006080 SO2X Inorganic materials 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 42
- 229940124530 sulfonamide Drugs 0.000 description 31
- QLRBNEZOQPLERN-UHFFFAOYSA-N (sulfonylamino)benzene Chemical compound O=S(=O)=NC1=CC=CC=C1 QLRBNEZOQPLERN-UHFFFAOYSA-N 0.000 description 14
- DEVUYWTZRXOMSI-UHFFFAOYSA-N (sulfamoylamino)benzene Chemical compound NS(=O)(=O)NC1=CC=CC=C1 DEVUYWTZRXOMSI-UHFFFAOYSA-N 0.000 description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 11
- 239000000306 component Substances 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 9
- GUYMMHOQXYZMJQ-UHFFFAOYSA-N n-ethyl-3-methylaniline Chemical compound CCNC1=CC=CC(C)=C1 GUYMMHOQXYZMJQ-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ORMYFMULKFJJIW-UHFFFAOYSA-N 2-[(4-amino-3-chlorophenyl)sulfonyl-methylamino]ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(C)S(=O)(=O)C1=CC=C(N)C(Cl)=C1 ORMYFMULKFJJIW-UHFFFAOYSA-N 0.000 description 3
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- NYNTWCLRIPGCIK-UHFFFAOYSA-N 1-chloro-3-(sulfonylamino)benzene Chemical compound S(=O)(=O)=NC1=CC=CC(=C1)Cl NYNTWCLRIPGCIK-UHFFFAOYSA-N 0.000 description 2
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 2
- JBXZCPXEYAEMJS-UHFFFAOYSA-N 2,5-dichloro-4-nitroaniline Chemical compound NC1=CC(Cl)=C([N+]([O-])=O)C=C1Cl JBXZCPXEYAEMJS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 2
- OCKRQFFXSXLNBJ-UHFFFAOYSA-N 2-[(4-amino-2,5-dichlorophenyl)sulfonylamino]ethanesulfonic acid Chemical compound NC1=CC(Cl)=C(S(=O)(=O)NCCS(O)(=O)=O)C=C1Cl OCKRQFFXSXLNBJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SZJQZIAFUYUGDD-UHFFFAOYSA-N 2-[(4-amino-3,5-dichlorophenyl)sulfonylamino]ethanesulfonic acid Chemical compound NC1=C(Cl)C=C(S(=O)(=O)NCCS(O)(=O)=O)C=C1Cl SZJQZIAFUYUGDD-UHFFFAOYSA-N 0.000 description 2
- OCWOYADFVCAJKK-UHFFFAOYSA-N 2-[(4-amino-3-chlorophenyl)sulfonyl-ethylamino]ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(CC)S(=O)(=O)C1=CC=C(N)C(Cl)=C1 OCWOYADFVCAJKK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- 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 2
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- PSPNSDSIAHXGNZ-UHFFFAOYSA-N 4-benzylsulfonyl-2,5-dichloroaniline Chemical compound C(C1=CC=CC=C1)S(=O)(=O)C1=C(C=C(C(=C1)Cl)N)Cl PSPNSDSIAHXGNZ-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- IUSARBWRQIXKOB-UHFFFAOYSA-N n-(ethylsulfamoyl)aniline Chemical compound CCNS(=O)(=O)NC1=CC=CC=C1 IUSARBWRQIXKOB-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000001174 sulfone group Chemical group 0.000 description 2
- 150000004992 toluidines Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MEYFKMASGCENBJ-UHFFFAOYSA-N (3-amino-4-chlorophenyl)sulfonylmethanesulfonamide Chemical compound NC1=CC(S(=O)(=O)CS(N)(=O)=O)=CC=C1Cl MEYFKMASGCENBJ-UHFFFAOYSA-N 0.000 description 1
- AHCDKORMOOTCED-UHFFFAOYSA-N (4-amino-3-chlorophenyl)sulfonylmethanesulfonamide Chemical compound NC1=CC=C(S(=O)(=O)CS(N)(=O)=O)C=C1Cl AHCDKORMOOTCED-UHFFFAOYSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-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
- BONRWBGSMDFTLR-UHFFFAOYSA-N 1-(3-amino-4-chlorophenyl)sulfonylbutane-1-sulfonamide Chemical compound CCCC(S(N)(=O)=O)S(=O)(=O)C1=CC=C(Cl)C(N)=C1 BONRWBGSMDFTLR-UHFFFAOYSA-N 0.000 description 1
- APBOPGBSILRNEQ-UHFFFAOYSA-N 1-(4-amino-2,5-dichlorophenyl)sulfonylpropane-1-sulfonamide Chemical compound CCC(S(N)(=O)=O)S(=O)(=O)C1=CC(Cl)=C(N)C=C1Cl APBOPGBSILRNEQ-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
- SYRBOMODLUADBZ-RNIAWFEPSA-N 1-[(E)-[(E)-(2-hydroxynaphthalen-1-yl)methylidenehydrazinylidene]methyl]naphthalen-2-ol Chemical compound N(\N=C\C1=C(C=CC2=CC=CC=C12)O)=C/C1=C(C=CC2=CC=CC=C12)O SYRBOMODLUADBZ-RNIAWFEPSA-N 0.000 description 1
- RWGAKTPRPJLVFG-UHFFFAOYSA-N 1-[4-amino-2-(trifluoromethyl)phenyl]sulfonylbutane-1-sulfonamide Chemical compound CCCC(S(N)(=O)=O)S(=O)(=O)C1=CC=C(N)C=C1C(F)(F)F RWGAKTPRPJLVFG-UHFFFAOYSA-N 0.000 description 1
- CTTAAFZLULCNLS-UHFFFAOYSA-N 1-[4-amino-3-(trifluoromethyl)phenyl]sulfonylbutane-1-sulfonamide Chemical compound CCCC(S(N)(=O)=O)S(=O)(=O)C1=CC=C(N)C(C(F)(F)F)=C1 CTTAAFZLULCNLS-UHFFFAOYSA-N 0.000 description 1
- CNPMFVKGCISFKW-UHFFFAOYSA-N 1-[4-amino-5-bromo-2-(trifluoromethyl)phenyl]sulfonylbutane-1-sulfonamide Chemical compound CCCC(S(N)(=O)=O)S(=O)(=O)C1=CC(Br)=C(N)C=C1C(F)(F)F CNPMFVKGCISFKW-UHFFFAOYSA-N 0.000 description 1
- QKVWIVSKKUXSTP-UHFFFAOYSA-N 1-bromo-2-(sulfonylamino)benzene Chemical compound BrC1=C(N=S(=O)=O)C=CC=C1 QKVWIVSKKUXSTP-UHFFFAOYSA-N 0.000 description 1
- UYWFQLKQXIGHPB-UHFFFAOYSA-N 1-chloro-3-(sulfamoylamino)benzene Chemical compound NS(=O)(=O)NC1=CC=CC(Cl)=C1 UYWFQLKQXIGHPB-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- LTSXZCHTTWKCNN-UHFFFAOYSA-N 2,4-dichloro-5-methylsulfonylaniline Chemical compound ClC1=C(N)C=C(C(=C1)Cl)S(=O)(=O)C LTSXZCHTTWKCNN-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
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- AZFFUTYTLIBNIR-UHFFFAOYSA-N 2,5-dichloro-4-ethylsulfonylaniline Chemical compound C(C)S(=O)(=O)C1=C(C=C(C(=C1)Cl)N)Cl AZFFUTYTLIBNIR-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
- OGSFKOQHKXGPJW-UHFFFAOYSA-N 2,5-dichloro-4-piperidin-1-ylsulfonylaniline Chemical compound C1=C(Cl)C(N)=CC(Cl)=C1S(=O)(=O)N1CCCCC1 OGSFKOQHKXGPJW-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
- ZTDPMTHDRQBQRB-UHFFFAOYSA-N 2,6-dichloro-4-ethylsulfonylaniline Chemical compound C(C)S(=O)(=O)C1=CC(=C(C(=C1)Cl)N)Cl ZTDPMTHDRQBQRB-UHFFFAOYSA-N 0.000 description 1
- IKJZTRFRAPNILB-UHFFFAOYSA-N 2,6-dichloro-4-propylsulfonylaniline Chemical compound C(CC)S(=O)(=O)C1=CC(=C(C(=C1)Cl)N)Cl IKJZTRFRAPNILB-UHFFFAOYSA-N 0.000 description 1
- RGOZZPZIEYXSJH-UHFFFAOYSA-N 2-(3-amino-4-chlorophenyl)sulfonylbenzenesulfonamide Chemical compound C1=C(Cl)C(N)=CC(S(=O)(=O)C=2C(=CC=CC=2)S(N)(=O)=O)=C1 RGOZZPZIEYXSJH-UHFFFAOYSA-N 0.000 description 1
- UCIGKQVKTKABHG-UHFFFAOYSA-N 2-(4-amino-2,5-dibromophenyl)sulfonylbenzenesulfonamide Chemical compound C1=C(Br)C(N)=CC(Br)=C1S(=O)(=O)C1=CC=CC=C1S(N)(=O)=O UCIGKQVKTKABHG-UHFFFAOYSA-N 0.000 description 1
- FBBCLTHEMYQSPL-UHFFFAOYSA-N 2-(4-amino-2,5-dichlorophenyl)sulfonylbenzenesulfonamide Chemical compound C1=C(Cl)C(N)=CC(Cl)=C1S(=O)(=O)C1=CC=CC=C1S(N)(=O)=O FBBCLTHEMYQSPL-UHFFFAOYSA-N 0.000 description 1
- YNZIPAWTXINRHI-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)sulfonylbenzenesulfonamide Chemical compound C1=C(Cl)C(N)=C(Cl)C=C1S(=O)(=O)C1=CC=CC=C1S(N)(=O)=O YNZIPAWTXINRHI-UHFFFAOYSA-N 0.000 description 1
- WCDHPZSZSIRHKP-UHFFFAOYSA-N 2-(4-amino-3-chlorophenyl)sulfonylbenzenesulfonamide Chemical compound C1=C(Cl)C(N)=CC=C1S(=O)(=O)C1=CC=CC=C1S(N)(=O)=O WCDHPZSZSIRHKP-UHFFFAOYSA-N 0.000 description 1
- BANNTZRSUOTALF-UHFFFAOYSA-N 2-(5-amino-2-methylphenyl)sulfonylbenzenesulfonamide Chemical compound CC1=CC=C(N)C=C1S(=O)(=O)C1=CC=CC=C1S(N)(=O)=O BANNTZRSUOTALF-UHFFFAOYSA-N 0.000 description 1
- JBCUKQQIWSWEOK-UHFFFAOYSA-N 2-(benzenesulfonyl)aniline Chemical compound NC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1 JBCUKQQIWSWEOK-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
- QSUGEEJULCHUHV-UHFFFAOYSA-N 2-[(4-amino-2,5-dichlorophenyl)sulfonyl-ethylamino]ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(CC)S(=O)(=O)C1=CC(Cl)=C(N)C=C1Cl QSUGEEJULCHUHV-UHFFFAOYSA-N 0.000 description 1
- ZNOLWOJLYPCJLD-UHFFFAOYSA-N 2-[(4-amino-2,5-dichlorophenyl)sulfonyl-methylamino]ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(C)S(=O)(=O)C1=CC(Cl)=C(N)C=C1Cl ZNOLWOJLYPCJLD-UHFFFAOYSA-N 0.000 description 1
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- DQNAQOYOSRJXFZ-UHFFFAOYSA-N 5-Amino-1-naphthalenesulfonic acid Chemical compound C1=CC=C2C(N)=CC=CC2=C1S(O)(=O)=O DQNAQOYOSRJXFZ-UHFFFAOYSA-N 0.000 description 1
- NPBHSNVITUSJGS-UHFFFAOYSA-N 5-amino-2,4-dichlorobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=C(Cl)C=C1Cl NPBHSNVITUSJGS-UHFFFAOYSA-N 0.000 description 1
- RKEBRHKROLVVPR-UHFFFAOYSA-N 5-amino-n-benzyl-2-chlorobenzenesulfonamide Chemical compound NC1=CC=C(Cl)C(S(=O)(=O)NCC=2C=CC=CC=2)=C1 RKEBRHKROLVVPR-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
- TYBFMVIWEVNLCE-UHFFFAOYSA-N 5-ethylsulfonyl-2-(trifluoromethyl)aniline Chemical compound C(C)S(=O)(=O)C1=CC(=C(C=C1)C(F)(F)F)N TYBFMVIWEVNLCE-UHFFFAOYSA-N 0.000 description 1
- UTBRTHNIBRUMFT-UHFFFAOYSA-N 5-methylsulfonyl-2-(trifluoromethyl)aniline Chemical compound CS(=O)(=O)C1=CC(=C(C=C1)C(F)(F)F)N UTBRTHNIBRUMFT-UHFFFAOYSA-N 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
- SEFBPSHUAFHLPT-UHFFFAOYSA-N C(C)S(=O)(=O)C1=CC(=CC(=C1N)C)Cl Chemical compound C(C)S(=O)(=O)C1=CC(=CC(=C1N)C)Cl SEFBPSHUAFHLPT-UHFFFAOYSA-N 0.000 description 1
- CTMXJUCLWYXNCO-UHFFFAOYSA-N C(C1=CC=CC=C1)S(=O)(=O)C1=CC(=C(C(=C1)Cl)N)Cl Chemical compound C(C1=CC=CC=C1)S(=O)(=O)C1=CC(=C(C(=C1)Cl)N)Cl CTMXJUCLWYXNCO-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OUZDJVLTDYMMLX-UHFFFAOYSA-N ClC1=C(C(=CC(=C1)C)Cl)NS(=O)=O.NC1=CC=CC=C1 Chemical compound ClC1=C(C(=CC(=C1)C)Cl)NS(=O)=O.NC1=CC=CC=C1 OUZDJVLTDYMMLX-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- LLWHAYMPHSJFDN-UHFFFAOYSA-N N-(3-aminophenyl)acetamide (sulfonylamino)benzene Chemical compound C(C)(=O)NC=1C=C(N)C=CC1.S(=O)(=O)=NC1=CC=CC=C1 LLWHAYMPHSJFDN-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- HSRZBAVZKFVRMO-UHFFFAOYSA-N [(sulfonylamino)sulfonylamino]benzene Chemical compound S(=O)(=O)=NS(=O)(=O)NC1=CC=CC=C1 HSRZBAVZKFVRMO-UHFFFAOYSA-N 0.000 description 1
- DACOCXURNRNDLX-UHFFFAOYSA-N [4-amino-2-chloro-5-(trifluoromethyl)phenyl]sulfonylmethanesulfonamide Chemical compound NC1=CC(Cl)=C(S(=O)(=O)CS(N)(=O)=O)C=C1C(F)(F)F DACOCXURNRNDLX-UHFFFAOYSA-N 0.000 description 1
- PLXAKIVCYSWZAB-UHFFFAOYSA-N [4-amino-3-(trifluoromethyl)phenyl]sulfonylmethanesulfonamide Chemical compound NC1=CC=C(S(=O)(=O)CS(N)(=O)=O)C=C1C(F)(F)F PLXAKIVCYSWZAB-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CLNUNIYTPDBRIM-UHFFFAOYSA-N butyl 4-amino-3-chlorobenzoate Chemical compound CCCCOC(=O)C1=CC=C(N)C(Cl)=C1 CLNUNIYTPDBRIM-UHFFFAOYSA-N 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
- 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
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 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
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- MFDTVONVIRHHBR-UHFFFAOYSA-N ethyl 4-amino-3-chlorobenzoate Chemical compound CCOC(=O)C1=CC=C(N)C(Cl)=C1 MFDTVONVIRHHBR-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- SXQCTESRRZBPHJ-UHFFFAOYSA-M lissamine rhodamine Chemical compound [Na+].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O SXQCTESRRZBPHJ-UHFFFAOYSA-M 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 229940012189 methyl orange Drugs 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- FTMVEUXYYDLYFH-UHFFFAOYSA-N n'-ethyl-n'-(3-methylphenyl)ethane-1,2-diamine Chemical compound NCCN(CC)C1=CC=CC(C)=C1 FTMVEUXYYDLYFH-UHFFFAOYSA-N 0.000 description 1
- HIPBGESCMZUXNS-UHFFFAOYSA-N n,3-diethylaniline Chemical compound CCNC1=CC=CC(CC)=C1 HIPBGESCMZUXNS-UHFFFAOYSA-N 0.000 description 1
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
- WHPIIGOGLISMED-UHFFFAOYSA-N n-[4-amino-5-chloro-2-(trifluoromethyl)phenyl]sulfonylnaphthalene-2-sulfonamide Chemical compound C1=C(Cl)C(N)=CC(C(F)(F)F)=C1S(=O)(=O)NS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 WHPIIGOGLISMED-UHFFFAOYSA-N 0.000 description 1
- OROYQHXCXXJBOP-UHFFFAOYSA-N n-ethyl-2,5-dimethylaniline Chemical compound CCNC1=CC(C)=CC=C1C OROYQHXCXXJBOP-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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 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
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 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
- 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
-
- 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
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C09B29/0085—Thiazoles or condensed thiazoles
-
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0801—Amino benzenes containing acid groups, e.g. COOH, SO3H, PO3H2, OSO3H, OPO3H2; SO2NHSO2R or salts thereof, R being hydrocarbonyls
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762640764 DE2640764A1 (de) | 1976-09-10 | 1976-09-10 | Azofarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1561420A true GB1561420A (en) | 1980-02-20 |
Family
ID=5987617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3695077A Expired GB1561420A (en) | 1976-09-10 | 1977-09-05 | Azo dyestuffs containing a phthalimido - alkyl group |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5334824A (enrdf_load_html_response) |
| DE (1) | DE2640764A1 (enrdf_load_html_response) |
| FR (1) | FR2364246A1 (enrdf_load_html_response) |
| GB (1) | GB1561420A (enrdf_load_html_response) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4447358A (en) * | 1980-10-16 | 1984-05-08 | Ciba-Geigy Corporation | Monoazo compounds |
| US5532345A (en) * | 1994-05-30 | 1996-07-02 | Ciba-Geigy Corporation | Fiber reactive phthalimidylazo dyes and use thereof |
| US5576445A (en) * | 1994-05-30 | 1996-11-19 | Ciba-Geigy Corporation | Intermediates for reactive dyes |
| CN101755012A (zh) * | 2007-07-20 | 2010-06-23 | 亨斯迈先进材料（瑞士）有限公司 | 偶氮染料 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3525733A (en) * | 1967-05-09 | 1970-08-25 | Eastman Kodak Co | Water-insoluble monoazo compounds containing an aniline coupling component substituted by both an acylamido group and a dicarboximido group |
| CH549627A (de) * | 1969-07-17 | 1974-05-31 | Sandoz Ag | Verfahren zur herstellung von azoverbindungen. |
| DE2263295A1 (de) * | 1972-12-23 | 1974-06-27 | Bayer Ag | Monoazofarbstoffe |
-
1976
- 1976-09-10 DE DE19762640764 patent/DE2640764A1/de not_active Withdrawn
-
1977
- 1977-09-05 GB GB3695077A patent/GB1561420A/en not_active Expired
- 1977-09-08 JP JP10732677A patent/JPS5334824A/ja active Pending
- 1977-09-09 FR FR7727395A patent/FR2364246A1/fr active Granted
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4447358A (en) * | 1980-10-16 | 1984-05-08 | Ciba-Geigy Corporation | Monoazo compounds |
| US5532345A (en) * | 1994-05-30 | 1996-07-02 | Ciba-Geigy Corporation | Fiber reactive phthalimidylazo dyes and use thereof |
| US5576445A (en) * | 1994-05-30 | 1996-11-19 | Ciba-Geigy Corporation | Intermediates for reactive dyes |
| US5665125A (en) * | 1994-05-30 | 1997-09-09 | Ciba-Geigy Corporation | Mixtures of fibre-reactive ring-opened phthalimidylazo dyes |
| CN101755012A (zh) * | 2007-07-20 | 2010-06-23 | 亨斯迈先进材料（瑞士）有限公司 | 偶氮染料 |
| CN101755012B (zh) * | 2007-07-20 | 2015-04-29 | 亨斯迈先进材料（瑞士）有限公司 | 偶氮染料 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5334824A (en) | 1978-03-31 |
| FR2364246B1 (enrdf_load_html_response) | 1981-08-28 |
| FR2364246A1 (fr) | 1978-04-07 |
| DE2640764A1 (de) | 1978-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |