DE2438496A1 - Disazofarbstoffe - Google Patents
DisazofarbstoffeInfo
- Publication number
- DE2438496A1 DE2438496A1 DE19742438496 DE2438496A DE2438496A1 DE 2438496 A1 DE2438496 A1 DE 2438496A1 DE 19742438496 DE19742438496 DE 19742438496 DE 2438496 A DE2438496 A DE 2438496A DE 2438496 A1 DE2438496 A1 DE 2438496A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- alkyl
- cyano
- methyl
- chlorine
- 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.)
- Withdrawn
Links
- 239000000975 dye Substances 0.000 title claims description 33
- LCZPIYCNOWJWPQ-UHFFFAOYSA-I disodium;chromium(3+);1-[(2-oxidonaphthalen-1-yl)diazenyl]-4-sulfonaphthalen-2-olate;3-oxido-4-[(2-oxidonaphthalen-1-yl)diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].[Cr+3].C12=CC=CC=C2C(S(=O)(=O)O)=CC([O-])=C1N=NC1=C([O-])C=CC2=CC=CC=C12.C1=CC=C2C(N=NC3=C4C=CC=CC4=CC=C3[O-])=C([O-])C=C(S([O-])(=O)=O)C2=C1 LCZPIYCNOWJWPQ-UHFFFAOYSA-I 0.000 title 1
- -1 carbalkoxy Chemical group 0.000 claims description 72
- 239000000460 chlorine Substances 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 44
- 150000002431 hydrogen Chemical class 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 12
- 230000008878 coupling Effects 0.000 claims description 11
- 238000010168 coupling process Methods 0.000 claims description 11
- 238000005859 coupling reaction Methods 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
- 238000004043 dyeing Methods 0.000 claims description 5
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000005521 carbonamide group Chemical group 0.000 claims description 4
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 3
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
- 239000012209 synthetic fiber Substances 0.000 claims description 3
- 229920002994 synthetic fiber Polymers 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- GCDUIEMBXFSFLI-UHFFFAOYSA-N 2-cyanoethyl hypochlorite Chemical compound ClOCCC#N GCDUIEMBXFSFLI-UHFFFAOYSA-N 0.000 claims description 2
- XSFKCGABINPZRK-UHFFFAOYSA-N 4-aminopyrazol-3-one Chemical class NC1=CN=NC1=O XSFKCGABINPZRK-UHFFFAOYSA-N 0.000 claims description 2
- RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical compound CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000000286 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 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 claims 1
- 150000001448 anilines Chemical class 0.000 claims 1
- 239000000987 azo dye Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002475 indoles Chemical class 0.000 claims 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 239000012362 glacial acetic acid Substances 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 8
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 229910014033 C-OH Inorganic materials 0.000 description 5
- 229910014570 C—OH Inorganic materials 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- MKJQYFVTEPGXIE-UHFFFAOYSA-N ethyl 2-aminothiophene-3-carboxylate Chemical compound CCOC(=O)C=1C=CSC=1N MKJQYFVTEPGXIE-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 3
- QLRBNEZOQPLERN-UHFFFAOYSA-N (sulfonylamino)benzene Chemical compound O=S(=O)=NC1=CC=CC=C1 QLRBNEZOQPLERN-UHFFFAOYSA-N 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- DEPDDPLQZYCHOH-UHFFFAOYSA-N 1h-imidazol-2-amine Chemical compound NC1=NC=CN1 DEPDDPLQZYCHOH-UHFFFAOYSA-N 0.000 description 2
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 description 2
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 2
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 2
- 229950011008 tetrachloroethylene Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 description 1
- MJIWQHRXSLOUJN-UHFFFAOYSA-N 1,2,4-triazin-3-amine Chemical compound NC1=NC=CN=N1 MJIWQHRXSLOUJN-UHFFFAOYSA-N 0.000 description 1
- WIJQCPIRWXSWQG-UHFFFAOYSA-N 1,2-benzothiazol-3-amine Chemical compound C1=CC=C2C(N)=NSC2=C1 WIJQCPIRWXSWQG-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- BJMUOUXGBFNLSN-UHFFFAOYSA-N 1,2-dimethylindole Chemical compound C1=CC=C2N(C)C(C)=CC2=C1 BJMUOUXGBFNLSN-UHFFFAOYSA-N 0.000 description 1
- QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 description 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- YDTDKKULPWTHRV-UHFFFAOYSA-N 1H-indazol-3-amine Chemical compound C1=CC=C2C(N)=NNC2=C1 YDTDKKULPWTHRV-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- GUMCAKKKNKYFEB-UHFFFAOYSA-N 2,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1Cl GUMCAKKKNKYFEB-UHFFFAOYSA-N 0.000 description 1
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
- LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-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
- JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-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
- HVKZGWQNGBBGAB-UHFFFAOYSA-N 2-[n-(2-methoxycarbonyloxyethyl)anilino]ethyl methyl carbonate Chemical compound COC(=O)OCCN(CCOC(=O)OC)C1=CC=CC=C1 HVKZGWQNGBBGAB-UHFFFAOYSA-N 0.000 description 1
- YJTBHWXNEMGNDC-UHFFFAOYSA-N 2-amino-1,3-thiazole-5-carbonitrile Chemical compound NC1=NC=C(C#N)S1 YJTBHWXNEMGNDC-UHFFFAOYSA-N 0.000 description 1
- DQSGHOSRHBJAKC-UHFFFAOYSA-N 2-amino-3h-thiophene-2-carboxylic acid Chemical compound OC(=O)C1(N)CC=CS1 DQSGHOSRHBJAKC-UHFFFAOYSA-N 0.000 description 1
- ANQMZJYXJPAMMR-UHFFFAOYSA-N 2-amino-4-(3-nitrophenyl)thiophene-3-carbonitrile Chemical compound N#CC1=C(N)SC=C1C1=CC=CC([N+]([O-])=O)=C1 ANQMZJYXJPAMMR-UHFFFAOYSA-N 0.000 description 1
- WIBSUGRBLQDHRV-UHFFFAOYSA-N 2-amino-4-ethylthiophene-3-carbonitrile Chemical compound CCC1=CSC(N)=C1C#N WIBSUGRBLQDHRV-UHFFFAOYSA-N 0.000 description 1
- AXLIJQRGPVJGSO-UHFFFAOYSA-N 2-amino-4-methylthiophene-3-carboxamide Chemical compound CC1=CSC(N)=C1C(N)=O AXLIJQRGPVJGSO-UHFFFAOYSA-N 0.000 description 1
- XVGHZFWFGXDIOU-UHFFFAOYSA-N 2-aminothiophene-3-carbonitrile Chemical compound NC=1SC=CC=1C#N XVGHZFWFGXDIOU-UHFFFAOYSA-N 0.000 description 1
- CGPPWNTVTNCHDO-UHFFFAOYSA-N 2-bromo-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Br CGPPWNTVTNCHDO-UHFFFAOYSA-N 0.000 description 1
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 1
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 1
- 125000006012 2-chloroethoxy group Chemical group 0.000 description 1
- UWIWGZCNYRBVJL-UHFFFAOYSA-N 2-chloronaphthalen-1-amine Chemical compound C1=CC=C2C(N)=C(Cl)C=CC2=C1 UWIWGZCNYRBVJL-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- BWNBLGQCCSCCHF-UHFFFAOYSA-N 2-ethyl-1h-indole Chemical compound C1=CC=C2NC(CC)=CC2=C1 BWNBLGQCCSCCHF-UHFFFAOYSA-N 0.000 description 1
- YRGYYQCOWUULNF-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=CC(=O)NC(O)=C1C#N YRGYYQCOWUULNF-UHFFFAOYSA-N 0.000 description 1
- HYEVLHRMEDHJJF-UHFFFAOYSA-N 2-methyl-1-(2-phenylindol-1-yl)propan-2-ol Chemical compound C=1C2=CC=CC=C2N(CC(C)(O)C)C=1C1=CC=CC=C1 HYEVLHRMEDHJJF-UHFFFAOYSA-N 0.000 description 1
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- DLURHXYXQYMPLT-UHFFFAOYSA-N 2-nitro-p-toluidine Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1 DLURHXYXQYMPLT-UHFFFAOYSA-N 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 1
- NPCCPMHHNIOSHL-UHFFFAOYSA-N 3-(n-ethyl-3-methylanilino)propanenitrile Chemical compound N#CCCN(CC)C1=CC=CC(C)=C1 NPCCPMHHNIOSHL-UHFFFAOYSA-N 0.000 description 1
- WYRNRZQRKCXPLA-UHFFFAOYSA-N 3-(n-ethylanilino)propanenitrile Chemical compound N#CCCN(CC)C1=CC=CC=C1 WYRNRZQRKCXPLA-UHFFFAOYSA-N 0.000 description 1
- USPVTJCHQHJFBQ-UHFFFAOYSA-N 3-chloro-n,n-diethylaniline Chemical compound CCN(CC)C1=CC=CC(Cl)=C1 USPVTJCHQHJFBQ-UHFFFAOYSA-N 0.000 description 1
- JUWWVCSNLLWQBL-UHFFFAOYSA-N 4,5-dimethyl-1h-imidazol-2-amine Chemical compound CC=1N=C(N)NC=1C JUWWVCSNLLWQBL-UHFFFAOYSA-N 0.000 description 1
- QPQKUYVSJWQSDY-CCEZHUSRSA-N 4-(phenylazo)aniline Chemical compound C1=CC(N)=CC=C1\N=N\C1=CC=CC=C1 QPQKUYVSJWQSDY-CCEZHUSRSA-N 0.000 description 1
- KBQAZLXJUFGPPI-UHFFFAOYSA-N 4-amino-2,5-dichloro-n,n-diethylbenzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC(Cl)=C(N)C=C1Cl KBQAZLXJUFGPPI-UHFFFAOYSA-N 0.000 description 1
- QHWDUJPWCGEBTH-UHFFFAOYSA-N 4-amino-n-phenylbenzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1 QHWDUJPWCGEBTH-UHFFFAOYSA-N 0.000 description 1
- IPMNLGOBXWTQRV-UHFFFAOYSA-N 4-aminobenzene-1,3-dicarbonitrile Chemical compound NC1=CC=C(C#N)C=C1C#N IPMNLGOBXWTQRV-UHFFFAOYSA-N 0.000 description 1
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- QFMJFXFXQAFGBO-UHFFFAOYSA-N 4-methoxy-2-nitroaniline Chemical compound COC1=CC=C(N)C([N+]([O-])=O)=C1 QFMJFXFXQAFGBO-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
- HOTZLWVITTVZGY-UHFFFAOYSA-N 4-nitro-2-(trifluoromethyl)aniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(F)(F)F HOTZLWVITTVZGY-UHFFFAOYSA-N 0.000 description 1
- PYSJLPAOBIGQPK-UHFFFAOYSA-N 4-phenyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=C1 PYSJLPAOBIGQPK-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- WRZOMWDJOLIVQP-UHFFFAOYSA-N 5-Chloro-ortho-toluidine Chemical compound CC1=CC=C(Cl)C=C1N WRZOMWDJOLIVQP-UHFFFAOYSA-N 0.000 description 1
- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 1
- DSBIJCMXAIKKKI-UHFFFAOYSA-N 5-nitro-o-toluidine Chemical compound CC1=CC=C([N+]([O-])=O)C=C1N DSBIJCMXAIKKKI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DZWTXWPRWRLHIL-UHFFFAOYSA-N 6-methyl-1,3-benzothiazol-2-amine Chemical compound CC1=CC=C2N=C(N)SC2=C1 DZWTXWPRWRLHIL-UHFFFAOYSA-N 0.000 description 1
- PLHOLGSXQBLUTF-UHFFFAOYSA-N 6-nitro-1,2-benzothiazol-3-amine Chemical compound [O-][N+](=O)C1=CC=C2C(N)=NSC2=C1 PLHOLGSXQBLUTF-UHFFFAOYSA-N 0.000 description 1
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
- ZRSKSQHEOZFGLJ-UHFFFAOYSA-N ammonium adipate Chemical compound [NH4+].[NH4+].[O-]C(=O)CCCCC([O-])=O ZRSKSQHEOZFGLJ-UHFFFAOYSA-N 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 1
- DAOPOOMCXJPWPK-UHFFFAOYSA-N benzyl 4-aminobenzoate Chemical compound C1=CC(N)=CC=C1C(=O)OCC1=CC=CC=C1 DAOPOOMCXJPWPK-UHFFFAOYSA-N 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 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
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-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
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- LZXXNPOYQCLXRS-UHFFFAOYSA-N methyl 4-aminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1 LZXXNPOYQCLXRS-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- GDIAEVRAHCYWGJ-UHFFFAOYSA-N n,n-diethyl-2,5-dimethoxyaniline Chemical compound CCN(CC)C1=CC(OC)=CC=C1OC GDIAEVRAHCYWGJ-UHFFFAOYSA-N 0.000 description 1
- KGFAREHEJGDILZ-UHFFFAOYSA-N n,n-diethyl-3-methoxyaniline Chemical compound CCN(CC)C1=CC=CC(OC)=C1 KGFAREHEJGDILZ-UHFFFAOYSA-N 0.000 description 1
- XLEMRIJDZGESRG-UHFFFAOYSA-N n,n-diethylnaphthalen-1-amine Chemical compound C1=CC=C2C(N(CC)CC)=CC=CC2=C1 XLEMRIJDZGESRG-UHFFFAOYSA-N 0.000 description 1
- FGFMOJODEQZXPR-UHFFFAOYSA-N n,n-diethylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(N(CC)CC)=CC=C21 FGFMOJODEQZXPR-UHFFFAOYSA-N 0.000 description 1
- FPUKYOSOAAPHTN-UHFFFAOYSA-N n-[3-(diethylamino)phenyl]acetamide Chemical compound CCN(CC)C1=CC=CC(NC(C)=O)=C1 FPUKYOSOAAPHTN-UHFFFAOYSA-N 0.000 description 1
- LSYOTQKXIPGLDP-UHFFFAOYSA-N n-[3-(diethylamino)phenyl]methanesulfonamide Chemical compound CCN(CC)C1=CC=CC(NS(C)(=O)=O)=C1 LSYOTQKXIPGLDP-UHFFFAOYSA-N 0.000 description 1
- LXZGVFCKZRHKMU-UHFFFAOYSA-N n-benzyl-n-methylaniline Chemical compound C=1C=CC=CC=1N(C)CC1=CC=CC=C1 LXZGVFCKZRHKMU-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
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003431 oxalo group Chemical group 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
- 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
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/025—Disazo dyes containing acid groups, e.g. -COOH, -SO3H, -PO3H2, -OSO3H, -OPO2H2; Salts thereof
-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/16—Trisazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742438496 DE2438496A1 (de) | 1974-08-10 | 1974-08-10 | Disazofarbstoffe |
| CH1040275A CH590904A5 (enrdf_load_html_response) | 1974-08-10 | 1975-08-08 | |
| JP9599475A JPS5141734A (ja) | 1974-08-10 | 1975-08-08 | Jisuazosenryonoseizoho |
| FR7524857A FR2281408A1 (fr) | 1974-08-10 | 1975-08-08 | Colorants disazoiques, leur procede d'obtention et leurs applications |
| GB3318975A GB1461738A (en) | 1974-08-10 | 1975-08-08 | Disazo dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742438496 DE2438496A1 (de) | 1974-08-10 | 1974-08-10 | Disazofarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2438496A1 true DE2438496A1 (de) | 1976-02-26 |
Family
ID=5922900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742438496 Withdrawn DE2438496A1 (de) | 1974-08-10 | 1974-08-10 | Disazofarbstoffe |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5141734A (enrdf_load_html_response) |
| CH (1) | CH590904A5 (enrdf_load_html_response) |
| DE (1) | DE2438496A1 (enrdf_load_html_response) |
| FR (1) | FR2281408A1 (enrdf_load_html_response) |
| GB (1) | GB1461738A (enrdf_load_html_response) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57125262A (en) * | 1981-01-27 | 1982-08-04 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS57125263A (en) * | 1981-01-27 | 1982-08-04 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| DE3151114A1 (de) * | 1980-12-26 | 1982-08-12 | Mitsubishi Chemical Industries, Ltd., Tokyo | Disazofarbstoffe fuer polyesterfasern |
| JPS57145154A (en) * | 1981-03-04 | 1982-09-08 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS57207649A (en) * | 1981-06-18 | 1982-12-20 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS57212255A (en) * | 1981-06-23 | 1982-12-27 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS585363A (ja) * | 1981-07-01 | 1983-01-12 | Mitsubishi Chem Ind Ltd | ポリエステル繊維用ジスアゾ染料 |
| DE3301822A1 (de) * | 1982-01-28 | 1983-08-04 | Research Association Of Synthetic Dyestuffs, Tokyo | Verfahren zur herstellung von disazo-farbstoffen |
| DE3318152A1 (de) * | 1982-05-18 | 1983-11-24 | Mitsubishi Chemical Industries, Ltd., Tokyo | Thiophen-diazo-farbstoffe zur faerbung zellulosehaltiger fasern |
| JPS5996172A (ja) * | 1982-11-24 | 1984-06-02 | Gosei Senriyou Gijutsu Kenkyu Kumiai | ポリエステル繊維用ジスアゾ染料 |
| JPS59168069A (ja) * | 1983-03-15 | 1984-09-21 | Gosei Senriyou Gijutsu Kenkyu Kumiai | ポリエステル繊維用配合染料 |
| JPS59197464A (ja) * | 1983-04-25 | 1984-11-09 | Mitsui Toatsu Chem Inc | 合成繊維用ジスアゾ染料 |
| US4908435A (en) * | 1987-02-27 | 1990-03-13 | Imperial Chemical Industries Plc | Aromatic disazo compounds having strong infra-red absorption |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2640542A1 (de) * | 1976-09-09 | 1978-03-23 | Basf Ag | Azofarbstoffe |
| GB1589927A (en) * | 1977-04-19 | 1981-05-20 | Ici Ltd | Disazo-thiazole dyestuffs |
| JPS5840352A (ja) * | 1981-09-02 | 1983-03-09 | Mitsubishi Chem Ind Ltd | ポリエステル繊維類用ジスアゾ染料 |
| JPS5838757A (ja) * | 1981-09-02 | 1983-03-07 | Gosei Senriyou Gijutsu Kenkyu Kumiai | ポリエステル繊維用ジスアゾ染料 |
| JPS5889654A (ja) * | 1981-11-24 | 1983-05-28 | Gosei Senriyou Gijutsu Kenkyu Kumiai | ジスアゾ系化合物 |
| JPS58198568A (ja) * | 1982-05-17 | 1983-11-18 | Gosei Senriyou Gijutsu Kenkyu Kumiai | ポリエステル繊維用配合染料 |
| JPS59152957A (ja) * | 1983-02-18 | 1984-08-31 | Gosei Senriyou Gijutsu Kenkyu Kumiai | ポリエステル繊維用アゾ染料 |
| JPH066675B2 (ja) * | 1986-04-21 | 1994-01-26 | 合成染料技術研究組合 | ジスアゾ化合物及びそれを用いる染色法 |
| JPH066674B2 (ja) * | 1986-04-21 | 1994-01-26 | 合成染料技術研究組合 | ジスアゾ化合物及びそれを用いる染色法 |
| DE3622297A1 (de) * | 1986-07-03 | 1988-01-07 | Basf Ag | Disazothiophenfarbstoffe |
| US5550218A (en) * | 1990-07-11 | 1996-08-27 | Sandoz Ltd. | Azo compounds having unsubstituted or substituted 2-phenoxycarbonylethyl groups |
| FR2664606A1 (fr) * | 1990-07-11 | 1992-01-17 | Sandoz Sa | Nouveaux composes azouiques, leur preparation et leur utilisation comme colorants de dispersion. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4264495A (en) * | 1972-05-15 | 1981-04-28 | Eastman Kodak Company | 2-Thienyl azo dyestuff compounds |
-
1974
- 1974-08-10 DE DE19742438496 patent/DE2438496A1/de not_active Withdrawn
-
1975
- 1975-08-08 GB GB3318975A patent/GB1461738A/en not_active Expired
- 1975-08-08 JP JP9599475A patent/JPS5141734A/ja active Pending
- 1975-08-08 CH CH1040275A patent/CH590904A5/xx not_active IP Right Cessation
- 1975-08-08 FR FR7524857A patent/FR2281408A1/fr active Granted
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4621136A (en) * | 1980-12-26 | 1986-11-04 | Mitsubishi Chemical Industries, Ltd. | Phenyl azo cyanothienyl azo anilino dyestuffs |
| DE3151114A1 (de) * | 1980-12-26 | 1982-08-12 | Mitsubishi Chemical Industries, Ltd., Tokyo | Disazofarbstoffe fuer polyesterfasern |
| JPS57125263A (en) * | 1981-01-27 | 1982-08-04 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS57125262A (en) * | 1981-01-27 | 1982-08-04 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS57145154A (en) * | 1981-03-04 | 1982-09-08 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS57207649A (en) * | 1981-06-18 | 1982-12-20 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS57212255A (en) * | 1981-06-23 | 1982-12-27 | Mitsubishi Chem Ind Ltd | Disazo dye for polyester fiber |
| JPS585363A (ja) * | 1981-07-01 | 1983-01-12 | Mitsubishi Chem Ind Ltd | ポリエステル繊維用ジスアゾ染料 |
| DE3301822A1 (de) * | 1982-01-28 | 1983-08-04 | Research Association Of Synthetic Dyestuffs, Tokyo | Verfahren zur herstellung von disazo-farbstoffen |
| DE3318152A1 (de) * | 1982-05-18 | 1983-11-24 | Mitsubishi Chemical Industries, Ltd., Tokyo | Thiophen-diazo-farbstoffe zur faerbung zellulosehaltiger fasern |
| GB2122633A (en) * | 1982-05-18 | 1984-01-18 | Mitsubishi Chem Ind | Thiophene disazo dyes for dyeing cellulose-containing fibers |
| US4801696A (en) * | 1982-05-18 | 1989-01-31 | Mitsubishi Chemical Industries Limited | Phenylazocyanothiopheneazoaniline dyes for dyeing cellulose-containing fibers in blue to bluish green shades |
| JPS5996172A (ja) * | 1982-11-24 | 1984-06-02 | Gosei Senriyou Gijutsu Kenkyu Kumiai | ポリエステル繊維用ジスアゾ染料 |
| JPS59168069A (ja) * | 1983-03-15 | 1984-09-21 | Gosei Senriyou Gijutsu Kenkyu Kumiai | ポリエステル繊維用配合染料 |
| JPS59197464A (ja) * | 1983-04-25 | 1984-11-09 | Mitsui Toatsu Chem Inc | 合成繊維用ジスアゾ染料 |
| US4908435A (en) * | 1987-02-27 | 1990-03-13 | Imperial Chemical Industries Plc | Aromatic disazo compounds having strong infra-red absorption |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2281408A1 (fr) | 1976-03-05 |
| CH590904A5 (enrdf_load_html_response) | 1977-08-31 |
| FR2281408B1 (enrdf_load_html_response) | 1979-05-18 |
| GB1461738A (en) | 1977-01-19 |
| JPS5141734A (ja) | 1976-04-08 |
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