BE432500A - - Google Patents

Info

Publication number

BE432500A

BE432500A BE432500DA BE432500A BE 432500 A BE432500 A BE 432500A BE 432500D A BE432500D A BE 432500DA BE 432500 A BE432500 A BE 432500A

Authority

BE

Belgium

Prior art keywords

sep

amino

pyrazolone

aryl

methyl

Prior art date

Links

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• 239000000975 dye Substances 0.000 claims description 30
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
• 239000003960 organic solvent Substances 0.000 claims description 9
• 239000011780 sodium chloride Substances 0.000 claims description 7
• 239000002253 acid Substances 0.000 claims description 6
• 150000001875 compounds Chemical class 0.000 claims description 6
• 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 4
• 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 4
• 125000000217 alkyl group Chemical group 0.000 claims description 3
• 230000000875 corresponding Effects 0.000 claims description 3
• 229910052736 halogen Inorganic materials 0.000 claims description 3
• 150000002367 halogens Chemical class 0.000 claims description 3
• 238000000034 method Methods 0.000 claims description 3
• 125000001424 substituent group Chemical group 0.000 claims description 3
• 150000001412 amines Chemical class 0.000 claims description 2
• 239000000470 constituent Substances 0.000 claims description 2
• 230000001808 coupling Effects 0.000 claims description 2
• 238000010168 coupling process Methods 0.000 claims description 2
• 238000005859 coupling reaction Methods 0.000 claims description 2
• -1 diazol compound Chemical class 0.000 claims description 2
• 230000001747 exhibiting Effects 0.000 claims description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims description 2
• 230000003381 solubilizing Effects 0.000 claims description 2
• 238000006467 substitution reaction Methods 0.000 claims description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims 1
• KAESVJOAVNADME-UHFFFAOYSA-N pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
• 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 104
• 239000004922 lacquer Substances 0.000 description 8
• KHBQMWCZKVMBLN-UHFFFAOYSA-N benzenesulfonimidic acid Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 7
• DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 239000002904 solvent Substances 0.000 description 5
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
• 239000000049 pigment Substances 0.000 description 3
• JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 2
• QELUYTUMUWHWMC-UHFFFAOYSA-N Edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 2
• 239000000987 azo dye Substances 0.000 description 2
• 229920002678 cellulose Polymers 0.000 description 2
• 239000001913 cellulose Substances 0.000 description 2
• 229920003086 cellulose ether Polymers 0.000 description 2
• 239000003086 colorant Substances 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• 150000002170 ethers Chemical class 0.000 description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 150000002430 hydrocarbons Chemical class 0.000 description 2
• LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
• CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
• 239000000843 powder Substances 0.000 description 2
• VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
• 239000001632 sodium acetate Substances 0.000 description 2
• 235000017281 sodium acetate Nutrition 0.000 description 2
• 235000011121 sodium hydroxide Nutrition 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• 239000008096 xylene Substances 0.000 description 2
• GTEOJYGNMFDLPG-KCRKGURFSA-N (4E)-2-methyl-4-[(4-phenyldiazenylphenyl)hydrazinylidene]cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C(C)=C\C1=N\NC1=CC=C(N=NC=2C=CC=CC=2)C=C1 GTEOJYGNMFDLPG-KCRKGURFSA-N 0.000 description 1
• ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 1
• XVISQAXVPDHRDA-UHFFFAOYSA-N 3-amino-4-ethoxy-N,N-dimethylbenzenesulfonamide Chemical compound CCOC1=CC=C(S(=O)(=O)N(C)C)C=C1N XVISQAXVPDHRDA-UHFFFAOYSA-N 0.000 description 1
• AFLAJUZTWQUJRZ-UHFFFAOYSA-N 4-amino-3-methoxy-N,N-dimethylbenzenesulfonamide Chemical compound COC1=CC(S(=O)(=O)N(C)C)=CC=C1N AFLAJUZTWQUJRZ-UHFFFAOYSA-N 0.000 description 1
• VTILWYBQQRECER-UHFFFAOYSA-N 5-sulfonylcyclohexa-1,3-diene Chemical compound O=S(=O)=C1CC=CC=C1 VTILWYBQQRECER-UHFFFAOYSA-N 0.000 description 1
• APVPOHHVBBYQAV-UHFFFAOYSA-N N-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
• AJDUTMFFZHIJEM-UHFFFAOYSA-N N-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
• GRTPAOVVVLZLDP-UHFFFAOYSA-N N-benzylbenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NCC1=CC=CC=C1 GRTPAOVVVLZLDP-UHFFFAOYSA-N 0.000 description 1
• 239000000020 Nitrocellulose Substances 0.000 description 1
• 229940081735 acetylcellulose Drugs 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 239000007900 aqueous suspension Substances 0.000 description 1
• 125000003710 aryl alkyl group Chemical group 0.000 description 1
• 125000003118 aryl group Chemical group 0.000 description 1
• 125000004429 atoms Chemical group 0.000 description 1
• 150000001555 benzenes Chemical class 0.000 description 1
• 238000004040 coloring Methods 0.000 description 1
• 150000008049 diazo compounds Chemical class 0.000 description 1
• 239000003925 fat Substances 0.000 description 1
• 239000010408 film Substances 0.000 description 1
• 125000000623 heterocyclic group Chemical group 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 230000001264 neutralization Effects 0.000 description 1
• 229920001220 nitrocellulos Polymers 0.000 description 1
• 239000004033 plastic Substances 0.000 description 1
• 229920003023 plastic Polymers 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 239000002966 varnish Substances 0.000 description 1
• 239000001043 yellow dye Substances 0.000 description 1