CH499595A - Verfahren zur Herstellung von sulfonsäuregruppenfreien Monoazofarbstoffen - Google Patents
Verfahren zur Herstellung von sulfonsäuregruppenfreien MonoazofarbstoffenInfo
- Publication number
- CH499595A CH499595A CH768768A CH768768A CH499595A CH 499595 A CH499595 A CH 499595A CH 768768 A CH768768 A CH 768768A CH 768768 A CH768768 A CH 768768A CH 499595 A CH499595 A CH 499595A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- amino
- pyrazolone
- methyl
- dione
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims abstract description 31
- 239000000049 pigment Substances 0.000 title claims description 12
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001412 amines Chemical class 0.000 claims abstract description 15
- 230000008878 coupling Effects 0.000 claims abstract description 14
- 238000010168 coupling process Methods 0.000 claims abstract description 14
- 238000005859 coupling reaction Methods 0.000 claims abstract description 14
- WGLQHUKCXBXUDV-UHFFFAOYSA-N 3-aminophthalic acid Chemical compound NC1=CC=CC(C(O)=O)=C1C(O)=O WGLQHUKCXBXUDV-UHFFFAOYSA-N 0.000 claims description 65
- QOMNJPSRBRDQSU-UHFFFAOYSA-N 5-aminobenzimidazol-2-one Chemical compound C1=C(N)C=CC2=NC(=O)N=C21 QOMNJPSRBRDQSU-UHFFFAOYSA-N 0.000 claims description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- HNWOXIYAKHJJIM-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoxalin-6-amine Chemical compound N1CCNC2=CC(N)=CC=C21 HNWOXIYAKHJJIM-UHFFFAOYSA-N 0.000 claims description 11
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 11
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 8
- AIHIKIZCFCEKEX-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinazolin-6-amine Chemical compound N1CNCC2=CC(N)=CC=C21 AIHIKIZCFCEKEX-UHFFFAOYSA-N 0.000 claims description 7
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 4
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 claims description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 150000002085 enols Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000000976 ink Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- JWIYQPMZNYYEGP-UHFFFAOYSA-N 1,2,3,4-tetrahydrophthalazin-6-amine Chemical compound NC=1C=C2CNNCC2=CC=1 JWIYQPMZNYYEGP-UHFFFAOYSA-N 0.000 claims description 3
- JYPZEZKWBAEHJG-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoxalin-5-amine Chemical compound N1CCNC2=C1C=CC=C2N JYPZEZKWBAEHJG-UHFFFAOYSA-N 0.000 claims description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 3
- 238000004043 dyeing Methods 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000003973 paint Substances 0.000 claims description 2
- 239000000123 paper Substances 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims 1
- 239000004753 textile Substances 0.000 claims 1
- USVVENVKYJZFMW-ONEGZZNKSA-N (e)-carboxyiminocarbamic acid Chemical compound OC(=O)\N=N\C(O)=O USVVENVKYJZFMW-ONEGZZNKSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 150000003931 anilides Chemical class 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- 150000008064 anhydrides Chemical class 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 9
- -1 Methoxy, ethoxy, butoxy groups Chemical group 0.000 description 8
- OXSANYRLJHSQEP-UHFFFAOYSA-N 4-aminophthalic acid Chemical class NC1=CC=C(C(O)=O)C(C(O)=O)=C1 OXSANYRLJHSQEP-UHFFFAOYSA-N 0.000 description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- QTTPQSUTBSWBFL-UHFFFAOYSA-N 2-amino-6-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC=CC(N)=C1C(O)=O QTTPQSUTBSWBFL-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- HQOBDLCAOWRBOU-UHFFFAOYSA-N 2-hydroxy-9h-carbazole-1-carboxylic acid Chemical compound C12=CC=CC=C2NC2=C1C=CC(O)=C2C(=O)O HQOBDLCAOWRBOU-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000000987 azo dye Substances 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 239000004922 lacquer Substances 0.000 description 3
- 239000001054 red pigment Substances 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000004408 titanium dioxide Substances 0.000 description 3
- YUSYMQJWNYFQSD-UHFFFAOYSA-N NC=1CC2NC(C(NC2=CC1)=O)=O Chemical compound NC=1CC2NC(C(NC2=CC1)=O)=O YUSYMQJWNYFQSD-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000005603 azodicarboxylic group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003791 organic solvent mixture Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 description 1
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 1
- OFUIFLZWMQEMFY-UHFFFAOYSA-N 1,2-dihydropyridazine-3,4-dione Chemical group O=C1C=CNNC1=O OFUIFLZWMQEMFY-UHFFFAOYSA-N 0.000 description 1
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- PRIUALOJYOZZOJ-UHFFFAOYSA-L 2-ethylhexyl 2-[dibutyl-[2-(2-ethylhexoxy)-2-oxoethyl]sulfanylstannyl]sulfanylacetate Chemical compound CCCCC(CC)COC(=O)CS[Sn](CCCC)(CCCC)SCC(=O)OCC(CC)CCCC PRIUALOJYOZZOJ-UHFFFAOYSA-L 0.000 description 1
- MSCMTURKIQRYPE-UHFFFAOYSA-N 2-hydroxyanthracene-1-carboxylic acid Chemical compound C1=CC=C2C=C3C(C(=O)O)=C(O)C=CC3=CC2=C1 MSCMTURKIQRYPE-UHFFFAOYSA-N 0.000 description 1
- RNELSSOIEGVRNT-UHFFFAOYSA-N 2-hydroxydibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC(O)=C2C(=O)O RNELSSOIEGVRNT-UHFFFAOYSA-N 0.000 description 1
- JBNOQRLGLQXWLO-UHFFFAOYSA-N 3-amino-4,5,6-trimethoxyphthalic acid Chemical compound NC1=C(C(C(=O)O)=C(C(=C1OC)OC)OC)C(=O)O JBNOQRLGLQXWLO-UHFFFAOYSA-N 0.000 description 1
- GLUAYYYGRPYVKP-UHFFFAOYSA-N 3-amino-4-methoxyphthalic acid Chemical compound NC1=C(C(C(=O)O)=CC=C1OC)C(=O)O GLUAYYYGRPYVKP-UHFFFAOYSA-N 0.000 description 1
- RRHKUABXGSMDHS-UHFFFAOYSA-N 3-amino-4-methylphthalic acid Chemical compound CC1=CC=C(C(O)=O)C(C(O)=O)=C1N RRHKUABXGSMDHS-UHFFFAOYSA-N 0.000 description 1
- VYZWDGSEJVEVSB-UHFFFAOYSA-N 3-amino-5-(trifluoromethyl)phthalic acid Chemical compound NC1=C(C(C(=O)O)=CC(=C1)C(F)(F)F)C(=O)O VYZWDGSEJVEVSB-UHFFFAOYSA-N 0.000 description 1
- WBIJIPZLUPLPQZ-UHFFFAOYSA-N 3-amino-5-cyanophthalic acid Chemical compound NC1=C(C(C(=O)O)=CC(=C1)C#N)C(=O)O WBIJIPZLUPLPQZ-UHFFFAOYSA-N 0.000 description 1
- VTZVIGBQAOXZAK-UHFFFAOYSA-N 3-amino-5-ethoxycarbonylphthalic acid Chemical compound NC1=C(C(C(=O)O)=CC(=C1)C(=O)OCC)C(=O)O VTZVIGBQAOXZAK-UHFFFAOYSA-N 0.000 description 1
- FDDAOHOLKFVTCU-UHFFFAOYSA-N 3-amino-5-methylphthalic acid Chemical compound NC1=C(C(C(=O)O)=CC(=C1)C)C(=O)O FDDAOHOLKFVTCU-UHFFFAOYSA-N 0.000 description 1
- GDXHUOFOZGPOEK-UHFFFAOYSA-N 3-amino-5-nitrophthalic acid Chemical compound NC1=C(C(C(=O)O)=CC(=C1)[N+](=O)[O-])C(=O)O GDXHUOFOZGPOEK-UHFFFAOYSA-N 0.000 description 1
- WWTKWTCRJNEVSL-UHFFFAOYSA-N 3-amino-6-(trifluoromethyl)phthalic acid Chemical compound NC1=C(C(C(=O)O)=C(C=C1)C(F)(F)F)C(=O)O WWTKWTCRJNEVSL-UHFFFAOYSA-N 0.000 description 1
- HGPYNPQGNLFTII-UHFFFAOYSA-N 3-amino-6-bromophthalic acid Chemical compound NC1=C(C(C(=O)O)=C(C=C1)Br)C(=O)O HGPYNPQGNLFTII-UHFFFAOYSA-N 0.000 description 1
- FFYKBPHPYPVCAI-UHFFFAOYSA-N 3-amino-6-chlorophthalic acid Chemical compound NC1=C(C(C(=O)O)=C(C=C1)Cl)C(=O)O FFYKBPHPYPVCAI-UHFFFAOYSA-N 0.000 description 1
- BJVULPHZPUKESP-UHFFFAOYSA-N 3-amino-6-cyanophthalic acid Chemical compound NC1=C(C(C(=O)O)=C(C=C1)C#N)C(=O)O BJVULPHZPUKESP-UHFFFAOYSA-N 0.000 description 1
- MDZJICZMKNDUDK-UHFFFAOYSA-N 3-amino-6-fluorophthalic acid Chemical compound NC1=C(C(C(=O)O)=C(C=C1)F)C(=O)O MDZJICZMKNDUDK-UHFFFAOYSA-N 0.000 description 1
- CXWHIRYROUZDOF-UHFFFAOYSA-N 3-amino-6-methoxyphthalic acid Chemical compound NC1=C(C(C(=O)O)=C(C=C1)OC)C(=O)O CXWHIRYROUZDOF-UHFFFAOYSA-N 0.000 description 1
- IHGCCIAXAAWTSR-UHFFFAOYSA-N 3-amino-6-nitrophthalic acid Chemical compound NC1=CC=C([N+]([O-])=O)C(C(O)=O)=C1C(O)=O IHGCCIAXAAWTSR-UHFFFAOYSA-N 0.000 description 1
- SIXWIUJQBBANGK-UHFFFAOYSA-N 4-(4-fluorophenyl)-1h-pyrazol-5-amine Chemical compound N1N=CC(C=2C=CC(F)=CC=2)=C1N SIXWIUJQBBANGK-UHFFFAOYSA-N 0.000 description 1
- PGJVSQNULKBTJW-UHFFFAOYSA-N 4-amino-5-methoxyphthalic acid Chemical compound COC1=CC(C(O)=O)=C(C(O)=O)C=C1N PGJVSQNULKBTJW-UHFFFAOYSA-N 0.000 description 1
- RUOKEIXYFOZSIS-UHFFFAOYSA-N 4-amino-5-nitrophthalic acid Chemical compound NC1=CC(C(O)=O)=C(C(O)=O)C=C1[N+]([O-])=O RUOKEIXYFOZSIS-UHFFFAOYSA-N 0.000 description 1
- CRXVBLLLPNWFBS-UHFFFAOYSA-N 4-aminobenzimidazol-2-one Chemical compound NC1=CC=CC2=NC(=O)N=C12 CRXVBLLLPNWFBS-UHFFFAOYSA-N 0.000 description 1
- OIVLITBTBDPEFK-UHFFFAOYSA-N 5,6-dihydrouracil Chemical compound O=C1CCNC(=O)N1 OIVLITBTBDPEFK-UHFFFAOYSA-N 0.000 description 1
- WUAZKQCAABBHSK-UHFFFAOYSA-N 5-amino-4,7-dimethylbenzimidazol-2-one Chemical compound CC1=CC(N)=C(C)C2=NC(=O)N=C12 WUAZKQCAABBHSK-UHFFFAOYSA-N 0.000 description 1
- ZCXIPVIGYBHUTQ-UHFFFAOYSA-N 5-amino-6-methyl-1,3-dihydrobenzimidazol-2-one Chemical compound C1=C(N)C(C)=CC2=C1NC(=O)N2 ZCXIPVIGYBHUTQ-UHFFFAOYSA-N 0.000 description 1
- QEVZFZGTXATUNR-UHFFFAOYSA-N 6-amino-1,3-benzodioxole-4,5-dicarboxylic acid Chemical compound NC1=C(C(C(=O)O)=C2C(=C1)OCO2)C(=O)O QEVZFZGTXATUNR-UHFFFAOYSA-N 0.000 description 1
- IMQWRQAIXSBGOV-UHFFFAOYSA-N 6-amino-3,4-dimethoxyphthalic acid Chemical compound NC1=C(C(C(=O)O)=C(C(=C1)OC)OC)C(=O)O IMQWRQAIXSBGOV-UHFFFAOYSA-N 0.000 description 1
- HAVSRAMAYFTTFU-UHFFFAOYSA-N 6-amino-4-chlorobenzimidazol-2-one Chemical compound C1=C(N)C=C(Cl)C2=NC(=O)N=C21 HAVSRAMAYFTTFU-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PCTPXAOHSBZIAQ-UHFFFAOYSA-N CC(CC(NC(C(Cl)=C(C(Cl)=C1Cl)Cl)=C1Cl)=O)=O Chemical compound CC(CC(NC(C(Cl)=C(C(Cl)=C1Cl)Cl)=C1Cl)=O)=O PCTPXAOHSBZIAQ-UHFFFAOYSA-N 0.000 description 1
- JVDRDXZIROPCPN-UHFFFAOYSA-N CC(CC(NC1=C(C)C=C(C)C(Cl)=C1)=O)=O Chemical compound CC(CC(NC1=C(C)C=C(C)C(Cl)=C1)=O)=O JVDRDXZIROPCPN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001470 diamides Chemical class 0.000 description 1
- MPCAOTRSCWFYIJ-UHFFFAOYSA-N diethyl 4-aminobenzene-1,2-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(N)C=C1C(=O)OCC MPCAOTRSCWFYIJ-UHFFFAOYSA-N 0.000 description 1
- VEJKSNHPNFHCLF-UHFFFAOYSA-N dimethyl 3-aminobenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=CC(N)=C1C(=O)OC VEJKSNHPNFHCLF-UHFFFAOYSA-N 0.000 description 1
- NTBHQNDXAJXRPU-UHFFFAOYSA-N dimethyl 4-aminobenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=C(N)C=C1C(=O)OC NTBHQNDXAJXRPU-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- YTKNYOWCICFXOW-UHFFFAOYSA-N n-(2,4-dichlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(Cl)C=C1Cl YTKNYOWCICFXOW-UHFFFAOYSA-N 0.000 description 1
- HGVIAKXYAZRSEG-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1C HGVIAKXYAZRSEG-UHFFFAOYSA-N 0.000 description 1
- FGVXALCWFWMFBD-UHFFFAOYSA-N n-(2,4-dinitrophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O FGVXALCWFWMFBD-UHFFFAOYSA-N 0.000 description 1
- BZKOGFAXBSPQRB-UHFFFAOYSA-N n-(2-chloro-4-nitrophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C([N+]([O-])=O)C=C1Cl BZKOGFAXBSPQRB-UHFFFAOYSA-N 0.000 description 1
- BFVHBHKMLIBQNN-UHFFFAOYSA-N n-(2-chlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1Cl BFVHBHKMLIBQNN-UHFFFAOYSA-N 0.000 description 1
- KYYRTDXOHQYZPO-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=CC=C1NC(=O)CC(C)=O KYYRTDXOHQYZPO-UHFFFAOYSA-N 0.000 description 1
- JTVHJWVDFCVGBG-UHFFFAOYSA-N n-(2-methyl-5-nitrophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC([N+]([O-])=O)=CC=C1C JTVHJWVDFCVGBG-UHFFFAOYSA-N 0.000 description 1
- TVZIWRMELPWPPR-UHFFFAOYSA-N n-(2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C TVZIWRMELPWPPR-UHFFFAOYSA-N 0.000 description 1
- NBLAONBKZUTBFR-UHFFFAOYSA-N n-(3-chloro-2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC(Cl)=C1C NBLAONBKZUTBFR-UHFFFAOYSA-N 0.000 description 1
- MOUVJGIRLPZEES-UHFFFAOYSA-N n-(4-chloro-2,5-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(NC(=O)CC(C)=O)=C(OC)C=C1Cl MOUVJGIRLPZEES-UHFFFAOYSA-N 0.000 description 1
- ODFRAIZRJMUPCP-UHFFFAOYSA-N n-(4-chloro-2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(Cl)C=C1C ODFRAIZRJMUPCP-UHFFFAOYSA-N 0.000 description 1
- KLMIREBDPKVUQJ-UHFFFAOYSA-N n-(4-chloro-2-nitrophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(Cl)C=C1[N+]([O-])=O KLMIREBDPKVUQJ-UHFFFAOYSA-N 0.000 description 1
- WWROGCAUSKGAMX-UHFFFAOYSA-N n-(4-ethoxyphenyl)-3-oxobutanamide Chemical compound CCOC1=CC=C(NC(=O)CC(C)=O)C=C1 WWROGCAUSKGAMX-UHFFFAOYSA-N 0.000 description 1
- QBHQQQKWEKZEHK-UHFFFAOYSA-N n-(4-methoxy-2-nitrophenyl)-3-oxobutanamide Chemical compound COC1=CC=C(NC(=O)CC(C)=O)C([N+]([O-])=O)=C1 QBHQQQKWEKZEHK-UHFFFAOYSA-N 0.000 description 1
- ZZSDMAAHJFGGSU-UHFFFAOYSA-N n-(4-methyl-2-nitrophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1[N+]([O-])=O ZZSDMAAHJFGGSU-UHFFFAOYSA-N 0.000 description 1
- MJGLMEMIYDUEHA-UHFFFAOYSA-N n-(4-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1 MJGLMEMIYDUEHA-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
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/32—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines
- C09B43/34—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines by reacting ortho- or peri-dicarboxylic dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0052727 | 1967-06-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH499595A true CH499595A (de) | 1970-11-30 |
Family
ID=7105687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH768768A CH499595A (de) | 1967-06-19 | 1968-05-24 | Verfahren zur Herstellung von sulfonsäuregruppenfreien Monoazofarbstoffen |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE716794A (en:Method) |
| CH (1) | CH499595A (en:Method) |
| DE (1) | DE1644218A1 (en:Method) |
| FR (1) | FR1570220A (en:Method) |
| GB (1) | GB1182859A (en:Method) |
| NL (1) | NL6808612A (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3734745A1 (de) * | 1987-10-09 | 1989-04-20 | Schering Ag | Tetrahydropyrrolo(2,1-c)(1,2,4)-thiadiazol-3-ylideniminobenzoxazinone und andere heterocyclisch substituierte azole und azine, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider wirkung |
-
1967
- 1967-06-19 DE DE19671644218 patent/DE1644218A1/de active Pending
-
1968
- 1968-05-24 CH CH768768A patent/CH499595A/de not_active IP Right Cessation
- 1968-05-30 GB GB2601968A patent/GB1182859A/en not_active Expired
- 1968-06-19 NL NL6808612A patent/NL6808612A/xx unknown
- 1968-06-19 BE BE716794D patent/BE716794A/xx unknown
- 1968-06-19 FR FR1570220D patent/FR1570220A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1644218A1 (de) | 1970-12-17 |
| BE716794A (en:Method) | 1968-12-02 |
| GB1182859A (en) | 1970-03-04 |
| NL6808612A (en:Method) | 1968-12-20 |
| FR1570220A (en:Method) | 1969-06-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |