JP2021508678A - 水溶性3−ケトクマリン - Google Patents
水溶性3−ケトクマリン Download PDFInfo
- Publication number
- JP2021508678A JP2021508678A JP2020532693A JP2020532693A JP2021508678A JP 2021508678 A JP2021508678 A JP 2021508678A JP 2020532693 A JP2020532693 A JP 2020532693A JP 2020532693 A JP2020532693 A JP 2020532693A JP 2021508678 A JP2021508678 A JP 2021508678A
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- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- compound
- unsubstituted
- formula
- 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.)
- Granted
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- CDSULTPOCMWJCM-UHFFFAOYSA-N 4h-chromene-2,3-dione Chemical compound C1=CC=C2OC(=O)C(=O)CC2=C1 CDSULTPOCMWJCM-UHFFFAOYSA-N 0.000 title abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 83
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- -1 piperidino, morpholino, piperazino Chemical group 0.000 claims description 38
- 239000003999 initiator Substances 0.000 claims description 18
- 239000000976 ink Substances 0.000 claims description 16
- 238000000576 coating method Methods 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000005977 Ethylene Substances 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 150000001412 amines Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 238000007641 inkjet printing Methods 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 150000001767 cationic compounds Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 150000002892 organic cations Chemical group 0.000 claims description 4
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 150000001449 anionic compounds Chemical group 0.000 claims description 2
- 150000002891 organic anions Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000000049 pigment Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000004821 distillation Methods 0.000 description 16
- 238000003756 stirring Methods 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000000178 monomer Substances 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- 229910052753 mercury Inorganic materials 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 125000004386 diacrylate group Chemical group 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 238000004383 yellowing Methods 0.000 description 5
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 3
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 0 CC(C=C(C=C(C(C1=CC=C*(*IC**)C=C1)=O)C(O1)=O)C1=C1)C=C1O* Chemical compound CC(C=C(C=C(C(C1=CC=C*(*IC**)C=C1)=O)C(O1)=O)C1=C1)C=C1O* 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 3
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000013011 aqueous formulation Substances 0.000 description 3
- OFDNITPEZYPPSO-UHFFFAOYSA-N butyl(oxo)tin;hydrate Chemical compound O.CCCC[Sn]=O OFDNITPEZYPPSO-UHFFFAOYSA-N 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 3
- 238000011002 quantification Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- PCLLJCFJFOBGDE-UHFFFAOYSA-N (5-bromo-2-chlorophenyl)methanamine Chemical compound NCC1=CC(Br)=CC=C1Cl PCLLJCFJFOBGDE-UHFFFAOYSA-N 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- YIJYFLXQHDOQGW-UHFFFAOYSA-N 2-[2,4,6-trioxo-3,5-bis(2-prop-2-enoyloxyethyl)-1,3,5-triazinan-1-yl]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN1C(=O)N(CCOC(=O)C=C)C(=O)N(CCOC(=O)C=C)C1=O YIJYFLXQHDOQGW-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- WYWZRNAHINYAEF-UHFFFAOYSA-N Padimate O Chemical compound CCCCC(CC)COC(=O)C1=CC=C(N(C)C)C=C1 WYWZRNAHINYAEF-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000007647 flexography Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 2
- FGBHUTWIQBXLLM-UHFFFAOYSA-N n-[6-(dimethylamino)hexyl]prop-2-enamide Chemical compound CN(C)CCCCCCNC(=O)C=C FGBHUTWIQBXLLM-UHFFFAOYSA-N 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- MXFQRSUWYYSPOC-UHFFFAOYSA-N (2,2-dimethyl-3-prop-2-enoyloxypropyl) prop-2-enoate Chemical class C=CC(=O)OCC(C)(C)COC(=O)C=C MXFQRSUWYYSPOC-UHFFFAOYSA-N 0.000 description 1
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 1
- LBDSQNRQXIKAGX-UHFFFAOYSA-N (2-methyl-3-prop-2-enoyloxypropyl) prop-2-enoate Chemical class C=CC(=O)OCC(C)COC(=O)C=C LBDSQNRQXIKAGX-UHFFFAOYSA-N 0.000 description 1
- PJAKWOZHTFWTNF-UHFFFAOYSA-N (2-nonylphenyl) prop-2-enoate Chemical compound CCCCCCCCCC1=CC=CC=C1OC(=O)C=C PJAKWOZHTFWTNF-UHFFFAOYSA-N 0.000 description 1
- IQGIEMYBDGDBMR-UHFFFAOYSA-N (3-methyl-5-prop-2-enoyloxypentyl) prop-2-enoate Chemical compound C=CC(=O)OCCC(C)CCOC(=O)C=C IQGIEMYBDGDBMR-UHFFFAOYSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical class CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 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
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- JUYQFRXNMVWASF-UHFFFAOYSA-M lithium;phenyl-(2,4,6-trimethylbenzoyl)phosphinate Chemical compound [Li+].CC1=CC(C)=CC(C)=C1C(=O)P([O-])(=O)C1=CC=CC=C1 JUYQFRXNMVWASF-UHFFFAOYSA-M 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UTBCRHAMJFMIIR-UHFFFAOYSA-N methyl 3-chloro-3-oxopropanoate Chemical compound COC(=O)CC(Cl)=O UTBCRHAMJFMIIR-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- DFENKTCEEGOWLB-UHFFFAOYSA-N n,n-bis(methylamino)-2-methylidenepentanamide Chemical compound CCCC(=C)C(=O)N(NC)NC DFENKTCEEGOWLB-UHFFFAOYSA-N 0.000 description 1
- DLJMSHXCPBXOKX-UHFFFAOYSA-N n,n-dibutylprop-2-enamide Chemical compound CCCCN(C(=O)C=C)CCCC DLJMSHXCPBXOKX-UHFFFAOYSA-N 0.000 description 1
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 description 1
- ZLSJVVLETDAEQY-UHFFFAOYSA-N n,n-dihexylprop-2-enamide Chemical compound CCCCCCN(C(=O)C=C)CCCCCC ZLSJVVLETDAEQY-UHFFFAOYSA-N 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- RKSYJNCKPUDQET-UHFFFAOYSA-N n,n-dipropylprop-2-enamide Chemical compound CCCN(CCC)C(=O)C=C RKSYJNCKPUDQET-UHFFFAOYSA-N 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- KCTMTGOHHMRJHZ-UHFFFAOYSA-N n-(2-methylpropoxymethyl)prop-2-enamide Chemical compound CC(C)COCNC(=O)C=C KCTMTGOHHMRJHZ-UHFFFAOYSA-N 0.000 description 1
- UTSYWKJYFPPRAP-UHFFFAOYSA-N n-(butoxymethyl)prop-2-enamide Chemical compound CCCCOCNC(=O)C=C UTSYWKJYFPPRAP-UHFFFAOYSA-N 0.000 description 1
- OOUWNHAYYDNAOD-UHFFFAOYSA-N n-[(dimethylamino)methyl]prop-2-enamide Chemical compound CN(C)CNC(=O)C=C OOUWNHAYYDNAOD-UHFFFAOYSA-N 0.000 description 1
- CXSANWNPQKKNJO-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]prop-2-enamide Chemical compound CCN(CC)CCNC(=O)C=C CXSANWNPQKKNJO-UHFFFAOYSA-N 0.000 description 1
- WDQKICIMIPUDBL-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]prop-2-enamide Chemical compound CN(C)CCNC(=O)C=C WDQKICIMIPUDBL-UHFFFAOYSA-N 0.000 description 1
- GFOCCLOYMMHTIU-UHFFFAOYSA-N n-[3-(diethylamino)propyl]prop-2-enamide Chemical compound CCN(CC)CCCNC(=O)C=C GFOCCLOYMMHTIU-UHFFFAOYSA-N 0.000 description 1
- OHLHOLGYGRKZMU-UHFFFAOYSA-N n-benzylprop-2-enamide Chemical compound C=CC(=O)NCC1=CC=CC=C1 OHLHOLGYGRKZMU-UHFFFAOYSA-N 0.000 description 1
- NOEQXGATUUVXRW-UHFFFAOYSA-N n-butan-2-ylprop-2-enamide Chemical compound CCC(C)NC(=O)C=C NOEQXGATUUVXRW-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PMJFVKWBSWWAKT-UHFFFAOYSA-N n-cyclohexylprop-2-enamide Chemical compound C=CC(=O)NC1CCCCC1 PMJFVKWBSWWAKT-UHFFFAOYSA-N 0.000 description 1
- XQPVIMDDIXCFFS-UHFFFAOYSA-N n-dodecylprop-2-enamide Chemical compound CCCCCCCCCCCCNC(=O)C=C XQPVIMDDIXCFFS-UHFFFAOYSA-N 0.000 description 1
- GCGQYJSQINRKQL-UHFFFAOYSA-N n-hexylprop-2-enamide Chemical compound CCCCCCNC(=O)C=C GCGQYJSQINRKQL-UHFFFAOYSA-N 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- SKSYKKPZQPJIHK-UHFFFAOYSA-N n-octan-3-ylprop-2-enamide Chemical compound CCCCCC(CC)NC(=O)C=C SKSYKKPZQPJIHK-UHFFFAOYSA-N 0.000 description 1
- AWGZKFQMWZYCHF-UHFFFAOYSA-N n-octylprop-2-enamide Chemical compound CCCCCCCCNC(=O)C=C AWGZKFQMWZYCHF-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- RZFODFPMOHAYIR-UHFFFAOYSA-N oxepan-2-one;prop-2-enoic acid Chemical compound OC(=O)C=C.O=C1CCCCCO1 RZFODFPMOHAYIR-UHFFFAOYSA-N 0.000 description 1
- FQMXGDWVUJLJLK-UHFFFAOYSA-N oxolan-2-ylmethyl prop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.C=CC(=O)OCC1CCCO1 FQMXGDWVUJLJLK-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical class CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920003009 polyurethane dispersion Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- QFXCGXNPCMKTJQ-UHFFFAOYSA-N prop-2-enoic acid;1,1,3-trimethylcyclohexane Chemical compound OC(=O)C=C.CC1CCCC(C)(C)C1 QFXCGXNPCMKTJQ-UHFFFAOYSA-N 0.000 description 1
- LBUSGXDHOHEPQQ-UHFFFAOYSA-N propane-1,1,1-triol Chemical class CCC(O)(O)O LBUSGXDHOHEPQQ-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- RSVDRWTUCMTKBV-UHFFFAOYSA-N sbb057044 Chemical compound C12CC=CC2C2CC(OCCOC(=O)C=C)C1C2 RSVDRWTUCMTKBV-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical group CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical group 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
- B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
- B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
- B41J2/01—Ink jet
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polymerisation Methods In General (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Pyrane Compounds (AREA)
Abstract
Description
式(I)
R1、R2は、それぞれ独立して、水素;C1-C12アルキル;置換又は未置換のアリール;置換又は未置換のヘテロアリール;置換又は未置換のC5-C6シクロアルキル;又はSH、-N(C1-C6アルキル)2、ピペリジノ、モルホリノ、ピペラジノ、-OH、-O(C1-C12アルキル)、-COOHにて置換されるC1-C12アルキル;又はC1-C12アルコキシであり;
nは0〜10の整数であり、nが0である場合、AはYに直接結合し;
Aは、CHR3、O、S又はNR4(ここで、R4は、水素又はC1-C6アルキル基である)であり;
R3は、水素;C1-C12アルキル;置換又は未置換のアリール;置換又は未置換のヘテロアリール;置換又は未置換のC5-C6シクロアルキル;又はSH、-N(C1-C6アルキル)2、ピペリジノ、モルホリノ、ピペラジノ、-OH、-O(C1-C12アルキル)、-COOHにて置換されるC1-C12アルキル;又はC1-C12アルコキシである;
Yは、
-CH2CH2CH2SO3-、-CH2CH2CH2CH2SO3-、
から選ばれる。)
(ここで、ALKはアルキル基、好ましくは、C1-C12アルキル基、例えば、メチル又はエチルであり、R1、R2、R3、及びR5 は上記のとおりである)。
I)a)水に溶解又は乳化したエチレン系不飽和化合物15〜40質量%、好ましくは、20〜40質量%、より好ましくは、20〜35質量%;
b)少なくとも1の上述のように定義される式(I)の化合物0.1〜10質量%、好ましくは、0.1〜8質量%、さらに好ましくは、0.2〜6質量%;
c)水20〜80質量%、好ましくは、20〜75質量%、さらに好ましくは、30〜70質量%
を含んでなる光重合性組成物を調製する工程;
II)任意に、プレ乾燥する工程;
III)前記工程I)又はII)の組成物を、光源にて、光重合する工程
を含んでなる。
[実施例]
窒素雰囲気下、0℃で撹拌しながら、エチル3-フェニルプロピオネート30.0 g(168.3 mモル)及び3-クロロ-3-オキソプロピオン酸メチル24.0 g(175.8 mモル)のジクロロメタン(250 ml)溶液に、塩化アンモニウム67.0 g(502.5 mモル)を少量ずつ添加した。室温において、4時間撹拌した後、反応混合物を氷水に注ぎ、得られた混合物を、30分間、撹拌下に維持した。ついで、有機相を分離し、水で洗浄し、硫酸ナトリウムにて乾燥し、濾過し、真空下での蒸留によって溶媒を除去して、黄色のオイル37.7 gを得た(収率80%)。
1H-NMR (CDCl3, δ ppm):1.22 (t, 3H), 2.65 (t, 2H), 3.05 (t, 2H), 3.75 (s, 3H), 3.98 (s, 2H), 4.10 (q, 2H), 7.30 (d, 2H), 7.85 (d, 2H)
実施例1の化合物34.1 g(122.5 mモル)及びピペリジン0.86 g(10.1 mモル)を、4.6-ジメトキシ-2-ヒドロキシ-ベンズアルデヒド22.3 g(122.4 mモル)のエタノール(100 ml)溶液に添加した。混合物を、還流下で、2時間撹拌し、ついで、室温に冷却した。反応生成物を濾過によって回収して、白−黄色の固体25.0 gを得た(収率50%)。
1H-NMR (CDCl3, δ ppm):1.23 (t, 3H), 2.65 (t, 2H), 3.10 (t, 2H), 3.89 (m, 6H), 4.12 (q, 2H), 6.30 (d, 1H), 6.45 (d, 1H), 7.30 (d, 2H), 7.79 (d, 2H), 8.40 (s, 1H)
150℃において、撹拌しながら、実施例2の化合物2.50 g(6.09 mモル)及びポリ(エチレングリコール)400 4.87 g(12.18 mモル)の混合物に、酸化水酸化ブチルスズ水和物1.27 g(6.08 mモル)を少量ずつ添加した。混合物を、150℃において、8時間撹拌し、蒸留によりエタノールを除去した。室温に冷却した後、反応混合物をジクロロメタンに溶解し、濾過した。濾液を、水で2回洗浄し、硫酸ナトリウムにて乾燥し、真空下での蒸留によって溶媒を除去した。粗製の生成物を、シリカゲル上でのフラッシュカラムクロマトグラフフィー(ジクロロメタン:メタノール=95:5)によって精製して、黄−褐色のオイル3.95 gを得た(収率85%)。
1H-NMR (CDCl3, δ ppm):2.70 (t, 2H), 3.00 (t, 2H), 3.50-3.70 (m, 32H), 3.90 (m, 6H), 4.20 (t, 2H), 6.30 (d, 1H), 6.45 (d, 1H), 7.30 (d, 2H), 7.75 (d, 2H), 8.40 (s, 1H)
150℃において、撹拌しながら、実施例2の化合物5.00 g(12.18 mモル)及びベンジルアルコール10.00 g(92.47 mモル)の混合物に、酸化水酸化ブチルスズ水和物2.54 g(12.16 mモル)を少量ずつ添加した。混合物を、150℃において、8時間撹拌し、蒸留によりエタノールを除去した。室温に冷却した後、反応混合物をエタノール30mlにて希釈し、濾過によって沈殿を回収した。沈殿物を、シリカゲル上でのフラッシュカラムクロマトグラフフィー(トルエン:酢酸エチル=90:10)によって精製して、白色の固体5.00 gを得た(収率87%)。
1H-NMR (CDCl3, δ ppm):2.70 (t, 2H), 3.05 (t, 2H), 3.90 (m, 6H), 5.12 (s, 2H), 6.30 (d, 1H), 6.45 (d, 1H), 7.25-7.40 (m, 7H), 7.75 (d, 2H), 8.4 (s, 1H)
6M塩酸水溶液20mlを、実施例4の化合物2.44 g(5.16 mモル)の1,4-ジオキサン(20ml)溶液に添加した。混合物を、還流下で、1時間撹拌し、ついで、室温に冷却し、真空下での蒸留によって溶媒を除去した。残渣をジクロロメタン25mlに懸濁化し、還流下で、1時間加熱し、ついで、室温に冷却した。濾過によって反応生成物を回収して、白−オレンジ色の固体1.58 gを得た(収率80%)。
1H-NMR (CDCl3, δ ppm):2.72 (t, 2H), 3.02 (t, 2H), 3.90 (m, 6H), 6.30 (d, 1H), 6.45 (d, 1H), 7.30 (d, 2H), 7.80 (d, 2H), 8.42 (s, 1H)
150℃において、撹拌しながら、実施例2の化合物2.50 g(6.09 mモル)及びポリ(エチレングリコール)600 8.22 g(13.70 mモル)の混合物に、酸化水酸化ブチルスズ水和物1.27 g(6.08 mモル)を少量ずつ添加した。混合物を、150℃において、8時間撹拌し、蒸留によりエタノールを除去した。室温に冷却した後、反応混合物をジクロロメタンに溶解し、濾過した。濾液を、水で2回洗浄し、硫酸ナトリウムにて乾燥し、真空下での蒸留によって溶媒を除去した。粗製の生成物を、シリカゲル上でのフラッシュカラムクロマトグラフフィー(ジクロロメタン:メタノール=90:10)によって精製して、黄−褐色のオイル5.11 gを得た(収率87%)。
1H-NMR (CDCl3, δ ppm):2.68 (t, 2H), 3.00 (t, 2H), 3.55-3.70 (m, 50H), 3.88 (d, 6H), 4.20 (t, 2H), 6.29 (d, 1H), 6.42 (d, 1H), 7.30 (d, 2H), 7.75 (d, 2H), 8.40 (s, 1H)
トリエタノールアミン0.975 g(6.54 mモル)を、実施例5の化合物2.50 g(6.54 mモル)のエタノール(40ml)懸濁液に添加した。混合物を、80℃において、1時間撹拌し、真空下での蒸留によって溶媒を除去して、白色の固体3.37 gを得た(収率97%)。
1H-NMR (D2O-DMSO-d6, δ ppm):2.65 (t, 2H), 3.15 (t, 2H), 3.30 (m, 6H), 3.95 (m, 6H), 4.09 (s, 3H), 4.11 (s, 3H), 6.66 (s, 1H), 6.75 (s, 1H), 7.65 (d, 2H), 7.90 (d, 2H), 8.45 (s, 1H)
1H-NMR (CDCl3, δ ppm):1.42 (m, 2H), 1.60 (m, 4H), 2.45 (m, 4H), 2.52 (s, 3H), 2.55 (m, 2H), 2.85 (m, 2H), 7.25 (d, 2H), 7.85 (d, 2H)
90〜95℃において、撹拌しながら、トルエン30ml中に、実施例10の化合物4.65 g(20.10 mモル)及び炭酸ジメチル18.11 g(201.04 mモル)を含有する混合物に、ナトリウムメトキシド4.34 g(24.12 mモル)の30%メタノール溶液を滴下した。混合物を、90〜95℃において、4時間撹拌し、蒸留によってメタノールを除去した。室温に冷却した後、反応混合物に、12%HCl水溶液60ml及び水40mlを、順次、添加した。ついで、水相を分離し、炭酸水素ナトリウム飽和溶液にて、pH7.4に塩基性化し、酢酸エチルにて抽出した。有機相を分離し、水にて洗浄し、硫酸ナトリウムにて乾燥し、濾過し、真空下での蒸留によって溶媒を除去して、黄色のオイル4.29 gを得た(収率74%)。
1H-NMR (CDCl3, δ ppm):1.45 (m, 2H), 1.62 (m, 4H), 2.45 (m, 4H), 2.59 (m, 2H), 2.88 (m, 2H), 3.75 (s, 3H), 3.96 (s, 2H), 7.30 (d, 2H), 7.85 (d, 2H)
実施例11の化合物4.20 g(14.51 mモル)及びモルホリン0.13 g(1.49 mモル)を、4,6-ジメトキシ-2-ヒドロキシ-ベンズアルデヒド2.64 g(14.49 mモル)のエタノール(20ml)溶液に添加した。混合物を、還流下で、2時間撹拌し、ついで、室温に冷却した。濾過によって、反応生成物を回収して、オフホワイト色の固体4.33 gを得た(収率71%)。
1H-NMR (CDCl3, δ ppm):1.50 (m, 2H), 1.75 (m, 4H), 2.62 (m, 4H), 2.75 (m, 2H), 3.00 (m, 2H), 3.88 (s, 3H), 3.89 (s, 3H), 6.27 (s, 1H), 6.45 (s, 1H), 7.30 (d, 2H), 7.87 (d, 2H), 8.40 (s, 1H)
35℃において、撹拌しながら、ヨウ化メチル4.64 g (32.69 mモル)を、実施例12の化合物3.00 g(7.12 mモル)のアセトニトリル(200 ml)溶液に添加した。35℃において、2.5時間撹拌した後、反応混合物を室温に冷却し、真空下での蒸留によって溶媒を除去した。残渣を、酢酸エチルにて採取し、濾過によって沈殿物を回収して、淡黄色の固体4.00 gを得た(収率100%)。
1H-NMR (DMSO-d6, δ ppm):0.75 (m, 2H), 1.00 (m, 4H), 2.29 (s, 3H), 2.32 (m, 2H), 2.57 (m, 4H), 2.77 (m, 2H), 3.09 (s, 3H), 3.10 (s, 3H), 5.75 (s, 1H), 5.90 (s, 1H), 6.67 (d, 2H), 7.00 (d, 2H), 7.45 (s, 1H)
撹拌しながら、塩化銀2.54 g(17.72 mモル)を、メタノール130 ml中に実施例13の化合物2.00 g(3.55 mモル)を含有する混合物に添加した。暗所にて、還流下、8時間撹拌した後、反応混合物を室温に冷却し、濾過し、真空下での蒸留によって溶媒を除去して、淡黄色の固体1.68 gを得た(収率100%)。
1H-NMR (DMSO-d6, δ ppm):0.75 (m, 2H), 1.00 (m, 4H), 2.29 (s, 3H), 2.32 (m, 2H), 2.57 (m, 4H), 2.77 (m, 2H), 3.09 (s, 3H), 3.10 (s, 3H), 5.75 (s, 1H), 5.90 (s, 1H), 6.67 (d, 2H), 7.00 (d, 2H), 7.45 (s, 1H)
本発明の3-ケトクマリンを、Omnirad 819 DW(IGM Resins B.V.)(COMP-1)と比較した。
[実施例15.1]
反応性テスト
透明な水性製剤
UCECOAT 7200及びEbecryl 350(Allnex)の混合物(質量比99:1)に、光開始剤及び共−開始剤(トリエタノールアミン)を、それぞれ、濃度3質量%で溶解して、テスト用の光重合性組成物を調製した。対照化合物Omnirad 819 DW(水中45質量%)(COMP-1)を、同じ活性含量を有するように、濃度6.6質量%で溶解した。
FT-IR(FT-IR 430-Jasco)のサンプル拠点に置いた光重合性組成物を、2つの異なる光源:
1)サンプルから25mmの距離及び角度30°で配置したLED光源(400 nm)(表1);
2)サンプルから65mmの距離及び角度30°で配置した水銀ランプ(160 W)(表2)
に露出した。
光重合の間に、一定の時間間隔で、IRスペクトルを取得し、アクリル系二重結合に割り当てられた1408 cm-1及び810 cm-1におけるピークの面積の経時的減少を、IRソフトウエアを使用して測定した。これは、重合度、従って、光開始剤の効力の定量を可能にする。
400 nmにおける結果(経時の重合度(%)として表示)を表1に示し、水銀ランプでの結果を表2に示す。
水性のブラックインクジェットインク
インクジェット印刷用の水性ブラックインクに、光開始剤及び共−開始剤(トリエタノールアミン)を、それぞれ、濃度5.0質量%で溶解することによって、テスト用の光重合性組成物を調製した。対照化合物Omnirad 819 DW(水中45質量%)(COMP-1)を、同じ活性含量を有するように、濃度11質量%で溶解した。
FT-IR(FT-IR 430-Jasco)のサンプル拠点に置いた光重合性組成物を、2つの異なる光源:
1)サンプルから25mmの距離及び30°の角度で配置したLED光源(400 nm)(表3);
2)サンプルから65mmの距離及び30°の角度で配置した水銀ランプ(160 W)(表4)
に露出した。
光重合の間に、一定の時間間隔で、IRスペクトルを取得し、アクリル系二重結合に割り当てられた1408 cm-1及び810 cm-1におけるピークの面積の経時的減少を、IRソフトウエアを使用して測定した。これは、重合度、従って、光開始剤の効力の定量を可能にする。
400 nmにおける結果(経時の重合度(%)として表示)を表3に示し、水銀ランプでの結果を表4に示す。
透明な水性インクジェットインク
インクジェット印刷用の透明な水性インクに、光開始剤及び共−開始剤(トリエタノールアミン)を、それぞれ、濃度5.0質量%で溶解することによって、テスト用の光重合性組成物を調製した。対照化合物Omnirad 819 DW(水中45質量%)(COMP-1)を、同じ活性含量を有するように、濃度11質量%で溶解した。2つの異なる条件を使用した:
A.溶液を調製し、40℃において、1時間撹拌し、ついで、室温に冷却し、光重合する;
B.溶液を調製し、40℃において、1時間撹拌し、ついで、室温に冷却し、0.45μmのMilliporeフィルターで濾過し、光重合する。
FT-IR(FT-IR 430-Jasco)のサンプル拠点に置いた光重合性組成物を、サンプルから25mmの距離及び30°の角度で配置したLED光源(400 nm)に露出した。
光重合の間に、一定の時間間隔で、IRスペクトルを取得し、アクリル系二重結合に割り当てられた1408 cm-1及び810 cm-1におけるピークの面積の経時的減少を、IRソフトウエアを使用して測定した。これは、重合度、従って、光開始剤の効力の定量を可能にする。
400 nmにおける結果(経時の重合度(%)として表示)を表5に示す。
Claims (19)
- 式(I)の化合物。
式(I)
R1、R2は、それぞれ独立して、水素;C1-C12アルキル;置換又は未置換のアリール;置換又は未置換のヘテロアリール;置換又は未置換のC5-C6シクロアルキル;又はSH、-N(C1-C6アルキル)2、ピペリジノ、モルホリノ、ピペラジノ、-OH、-O(C1-C12アルキル)、-COOHにて置換されるC1-C12アルキル;又はC1-C12アルコキシであり;
nは0〜10の整数であり、nが0である場合、AはYに直接結合し;
Aは、CHR3、O、S又はNR4(ここで、R4は、水素又はC1-C6アルキル基である)であり;
R3は、水素;C1-C12アルキル;置換又は未置換のアリール;置換又は未置換のヘテロアリール;置換又は未置換のC5-C6シクロアルキル;又はSH、-N(C1-C6アルキル)2、ピペリジノ、モルホリノ、ピペラジノ、-OH、-O(C1-C12アルキル)、-COOHにて置換される C1-C12アルキル;又はC1-C12アルコキシである;
Yは、
-CH2CH2CH2SO3-、-CH2CH2CH2CH2SO3-、
から選ばれる。) - nが0〜6である請求項1に記載の式(I)の化合物。
- AがCHR3である請求項1又は2に記載の式(I)の化合物。
- R1及びR2が、ともに、メチル基である請求項1〜4のいずれかに記載の式(I)の化合物。
- R3が水素である請求項1〜5のいずれかに記載の式(I)の化合物。
- 式(I)の化合物の、紫外光又はブルーライト誘発光重合法における光開始剤としての使用。
- インク、コーティング、又は三次元物体の硬化のための光重合法における請求項7に記載の使用。
- インクジェット印刷用インクのための光重合法における請求項7又は8に記載の使用。
- 少なくとも1の共−開始剤と組み合わされた請求項7〜9のいずれかに記載の使用。
- 共−開始剤がアミンである請求項10に記載の使用。
- 共−開始剤が、不飽和エチレン部分を有するアミンである請求項11に記載の使用。
- 水に溶解又は乳化された少なくとも1のエチレン系不飽和化合物、及び少なくとも1の共−開始剤と任意に組み合わされた、請求項1〜6のいずれかにおいて定義された式(I)の化合物を含んでなる光重合性組成物。
- 下記の工程:
I)a)水に溶解又は乳化した少なくとも1のエチレン系不飽和化合物15〜40質量%、好ましくは、20〜40質量%、より好ましくは、20〜35質量%;
b)少なくとも1の上述のように定義される式(I)の化合物0.1〜10質量%、好ましくは、0.1〜8質量%、さらに好ましくは、0.2〜6質量%;
c)水20〜80質量%、好ましくは、20〜75質量%、さらに好ましくは、30〜70質量%
を含んでなる光重合性組成物を調製する工程;
II)任意に、プレ乾燥する工程;
III)前記工程I)又はII)の組成物を、光源にて、光重合する工程
を含んでなる光重合法。 - 光重合を、波長200〜420 nmで発光するLED光源にて行う請求項14に記載の方法。
- 光重合を、波長365〜420 nmで発光するLED光源にて行う請求項15に記載の方法。
- さらに、光重合する前に、光重合性組成物を基板に塗布する工程を含んでなる請求項14又は16に記載の方法。
- 少なくとも1の共−開始剤も存在することを特徴とする請求項14〜17のいずれかに記載の方法。
- 請求項14〜18のいずれかに記載の方法によって調製された製品。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US201762598655P | 2017-12-14 | 2017-12-14 | |
US62/598,655 | 2017-12-14 | ||
PCT/IB2018/059703 WO2019116177A1 (en) | 2017-12-14 | 2018-12-06 | Water soluble 3-ketocoumarins |
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WO2023282045A1 (ja) * | 2021-07-05 | 2023-01-12 | 株式会社Adeka | 化合物、組成物、硬化物及び硬化物の製造方法 |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04145102A (ja) * | 1990-10-05 | 1992-05-19 | Toyo Ink Mfg Co Ltd | 可視光感光性樹脂組成物 |
JP2016510314A (ja) * | 2012-12-19 | 2016-04-07 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | ビスアシルホスフィン酸の誘導体、その製造および光開始剤としての使用 |
WO2019030631A1 (en) * | 2017-08-09 | 2019-02-14 | Igm Group Bv | MULTIFUNCTIONAL POLYMER PHOTO-INITIATORS |
JP7092887B2 (ja) * | 2017-12-11 | 2022-06-28 | アイジーエム レシンス イタリア ソチエタ レスポンサビリタ リミタータ | ベンゾイル-クマリン重合性光開始剤 |
Family Cites Families (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3844916A (en) | 1972-09-18 | 1974-10-29 | Desoto Inc | Radiation curable non-gelled michael addition reaction products |
DE2853921A1 (de) | 1978-12-14 | 1980-07-03 | Basf Ag | Strahlungshaertbare waessrige bindemitteldispersionen |
DE3069349D1 (en) * | 1979-06-18 | 1984-11-08 | Eastman Kodak Co | Co-initiator compositions for photopolymerization containing 3-acyl-substituted coumarins, photopolymerizable composition and photographic element |
DE2936039A1 (de) | 1979-09-06 | 1981-04-02 | Bayer Ag, 5090 Leverkusen | Wasserdispergierbare, durch strahlen vernetzbare bindemittel aus urethanacrylaten, ein verfahren zu ihrer herstellung sowie die verwendung dieser bindemittel in waessriger dispersion auf dem anstrich-, druckfarben- und textilsektor |
DE3005036A1 (de) | 1980-02-11 | 1981-08-27 | Basf Ag, 6700 Ludwigshafen | Strahlungshaertbare waessrige bindemitteldispersionen |
DE3017543A1 (de) | 1980-05-08 | 1981-11-26 | Bayer Ag, 5090 Leverkusen | Waessrige dispersionen auf basis von (meth)acrylsaeurealkylester-polymerisaten mit zwei ausgepraegten, praktisch sich nicht ueberlappenden maxima in der teilchengroessenverteilung innerhalb spezieller teilchengroessenbereiche, sowie verfahren zu ihrer herstellung und ihre verwendung |
GB2108487B (en) | 1981-11-03 | 1985-07-31 | Sericol Group Ltd | Water soluble thioxanthone photoinitiators |
US4602097A (en) | 1984-06-11 | 1986-07-22 | Ulano Corporation | Water soluble photoinitiator benzophenone and thioxanthenone ethoxy-ether derivatives |
DE3706355A1 (de) | 1987-02-27 | 1988-09-08 | Basf Ag | Additionsprodukte aus acrylaten und aminen sowie deren verwendung in strahlungshaertbaren massen |
DE4225921A1 (de) | 1992-08-05 | 1994-02-10 | Bayer Ag | Aminoacrylate, ein Verfahren zu ihrer Herstellung und ihre Verwendung |
EP0731121A3 (de) | 1995-03-09 | 1997-06-11 | Basf Ag | Aminomodifizierte Urethanacrylate |
CN100355743C (zh) * | 2003-12-26 | 2007-12-19 | 中国科学院理化技术研究所 | 以环烷烃酮类连接的3或4位羰基取代的香豆素酮及其合成方法和用途 |
ATE388655T1 (de) | 2005-10-28 | 2008-03-15 | Kuhn Rikon Ag | Schnellkochtopf |
JP4601009B2 (ja) * | 2007-03-30 | 2010-12-22 | 富士フイルム株式会社 | インクジェット記録用インクセット及びインクジェット記録方法 |
GB201005060D0 (en) | 2010-03-25 | 2010-05-12 | Davidson Robert S | Synergists |
CN102643599A (zh) * | 2012-04-18 | 2012-08-22 | 上海维凯化学品有限公司 | Uv-热塑树脂复合镭射镀铝涂料组合物 |
CN108707129A (zh) * | 2012-07-27 | 2018-10-26 | 太阳化学公司 | 作为油墨中的光引发剂和光敏剂的香豆素酮 |
ITVA20120041A1 (it) * | 2012-10-22 | 2014-04-23 | Lamberti Spa | 3-chetocumarine per fotopolimerizzazioni tramite led |
EP3148980B1 (en) | 2014-05-29 | 2020-12-09 | Sun Chemical Corporation | Water-based uv inkjet ink |
EP2960306B1 (en) | 2014-06-26 | 2020-12-23 | Agfa Nv | Aqueous radiation curable inkjet inks |
US10620972B2 (en) | 2015-07-16 | 2020-04-14 | Adobe Inc. | Processing touch gestures in hybrid applications |
US10519332B2 (en) | 2015-09-23 | 2019-12-31 | Sun Chemical Corporation | Waterbased UV inkjet ink containing synthetic thickener |
US11472972B2 (en) | 2016-06-17 | 2022-10-18 | Igm Group Bv | 3-ketocoumarins, a process for their preparation and their use as photoinitiators in photopolymerization reactions |
CN107915701B (zh) | 2016-10-10 | 2020-09-29 | 沈阳药科大学 | 一种PPARα/γ双重激动剂及其应用 |
CN106967027A (zh) * | 2017-03-15 | 2017-07-21 | 同济大学 | 新型香豆素化合物及其应用 |
-
2018
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- 2018-12-06 WO PCT/IB2018/059703 patent/WO2019116177A1/en unknown
- 2018-12-10 TW TW107144298A patent/TW201927762A/zh unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04145102A (ja) * | 1990-10-05 | 1992-05-19 | Toyo Ink Mfg Co Ltd | 可視光感光性樹脂組成物 |
JP2016510314A (ja) * | 2012-12-19 | 2016-04-07 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | ビスアシルホスフィン酸の誘導体、その製造および光開始剤としての使用 |
WO2019030631A1 (en) * | 2017-08-09 | 2019-02-14 | Igm Group Bv | MULTIFUNCTIONAL POLYMER PHOTO-INITIATORS |
JP7092887B2 (ja) * | 2017-12-11 | 2022-06-28 | アイジーエム レシンス イタリア ソチエタ レスポンサビリタ リミタータ | ベンゾイル-クマリン重合性光開始剤 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023282045A1 (ja) * | 2021-07-05 | 2023-01-12 | 株式会社Adeka | 化合物、組成物、硬化物及び硬化物の製造方法 |
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CN111601795A (zh) | 2020-08-28 |
WO2019116177A1 (en) | 2019-06-20 |
US20210070726A1 (en) | 2021-03-11 |
KR20200116079A (ko) | 2020-10-08 |
CN111601795B (zh) | 2024-03-19 |
JP7272553B2 (ja) | 2023-05-12 |
EP3724172A1 (en) | 2020-10-21 |
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