JP2019214735A - Led硬化性低移行性光開始剤 - Google Patents
Led硬化性低移行性光開始剤 Download PDFInfo
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- JP2019214735A JP2019214735A JP2019149050A JP2019149050A JP2019214735A JP 2019214735 A JP2019214735 A JP 2019214735A JP 2019149050 A JP2019149050 A JP 2019149050A JP 2019149050 A JP2019149050 A JP 2019149050A JP 2019214735 A JP2019214735 A JP 2019214735A
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- Prior art keywords
- methacrylate
- acrylate
- group
- moiety
- nitrogen
- 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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- 230000005012 migration Effects 0.000 title description 4
- 238000013508 migration Methods 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims abstract description 102
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 87
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims abstract description 86
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 75
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims abstract description 70
- 238000000034 method Methods 0.000 claims abstract description 56
- 239000000178 monomer Substances 0.000 claims abstract description 34
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 18
- 238000002156 mixing Methods 0.000 claims abstract description 7
- -1 azocanyl Chemical group 0.000 claims description 61
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 48
- 239000012965 benzophenone Substances 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 25
- 125000004193 piperazinyl group Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 22
- 238000000576 coating method Methods 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 18
- 125000003386 piperidinyl group Chemical group 0.000 claims description 17
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000003725 azepanyl group Chemical group 0.000 claims description 15
- 125000002393 azetidinyl group Chemical group 0.000 claims description 15
- 125000005466 alkylenyl group Chemical group 0.000 claims description 14
- 239000011248 coating agent Substances 0.000 claims description 14
- 239000008199 coating composition Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 12
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 10
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims description 9
- 230000001678 irradiating effect Effects 0.000 claims description 9
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 8
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 8
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 8
- 229910052753 mercury Inorganic materials 0.000 claims description 8
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 claims description 8
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 7
- FMQPBWHSNCRVQJ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C(F)(F)F)C(F)(F)F FMQPBWHSNCRVQJ-UHFFFAOYSA-N 0.000 claims description 6
- MNSWITGNWZSAMC-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl prop-2-enoate Chemical compound FC(F)(F)C(C(F)(F)F)OC(=O)C=C MNSWITGNWZSAMC-UHFFFAOYSA-N 0.000 claims description 6
- LMAUULKNZLEMGN-UHFFFAOYSA-N 1-ethyl-3,5-dimethylbenzene Chemical compound CCC1=CC(C)=CC(C)=C1 LMAUULKNZLEMGN-UHFFFAOYSA-N 0.000 claims description 6
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 claims description 6
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 6
- PTJDGKYFJYEAOK-UHFFFAOYSA-N 2-butoxyethyl prop-2-enoate Chemical compound CCCCOCCOC(=O)C=C PTJDGKYFJYEAOK-UHFFFAOYSA-N 0.000 claims description 6
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 claims description 6
- CHNGPLVDGWOPMD-UHFFFAOYSA-N 2-ethylbutyl 2-methylprop-2-enoate Chemical compound CCC(CC)COC(=O)C(C)=C CHNGPLVDGWOPMD-UHFFFAOYSA-N 0.000 claims description 6
- JGRXEBOFWPLEAV-UHFFFAOYSA-N 2-ethylbutyl prop-2-enoate Chemical compound CCC(CC)COC(=O)C=C JGRXEBOFWPLEAV-UHFFFAOYSA-N 0.000 claims description 6
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims description 6
- VWJAVBOLCVPIAK-UHFFFAOYSA-N 2-methoxybutyl 2-methylprop-2-enoate Chemical compound CCC(OC)COC(=O)C(C)=C VWJAVBOLCVPIAK-UHFFFAOYSA-N 0.000 claims description 6
- FURRSXHPLKQVIR-UHFFFAOYSA-N 2-methoxybutyl prop-2-enoate Chemical compound CCC(OC)COC(=O)C=C FURRSXHPLKQVIR-UHFFFAOYSA-N 0.000 claims description 6
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 6
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims description 6
- ILZXXGLGJZQLTR-UHFFFAOYSA-N 2-phenylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1 ILZXXGLGJZQLTR-UHFFFAOYSA-N 0.000 claims description 6
- HPSGLFKWHYAKSF-UHFFFAOYSA-N 2-phenylethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1=CC=CC=C1 HPSGLFKWHYAKSF-UHFFFAOYSA-N 0.000 claims description 6
- NWKKCUWIMOZYOO-UHFFFAOYSA-N 3-methoxybutyl 2-methylprop-2-enoate Chemical compound COC(C)CCOC(=O)C(C)=C NWKKCUWIMOZYOO-UHFFFAOYSA-N 0.000 claims description 6
- ZVYGIPWYVVJFRW-UHFFFAOYSA-N 3-methylbutyl prop-2-enoate Chemical compound CC(C)CCOC(=O)C=C ZVYGIPWYVVJFRW-UHFFFAOYSA-N 0.000 claims description 6
- MUPJJZVGSOUSFH-UHFFFAOYSA-N 4-(2-cyanoethyl)-4-nitroheptanedinitrile Chemical compound N#CCCC([N+](=O)[O-])(CCC#N)CCC#N MUPJJZVGSOUSFH-UHFFFAOYSA-N 0.000 claims description 6
- NUXLDNTZFXDNBA-UHFFFAOYSA-N 6-bromo-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(Br)C=C2NC(=O)C(C)OC2=C1 NUXLDNTZFXDNBA-UHFFFAOYSA-N 0.000 claims description 6
- RUZXDTHZHJTTRO-UHFFFAOYSA-N 7-amino-4h-1,4-benzoxazin-3-one Chemical compound N1C(=O)COC2=CC(N)=CC=C21 RUZXDTHZHJTTRO-UHFFFAOYSA-N 0.000 claims description 6
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 6
- QMEMFEMQJJOZGM-RMKNXTFCSA-N [(e)-3-phenylprop-2-enyl] prop-2-enoate Chemical compound C=CC(=O)OC\C=C\C1=CC=CC=C1 QMEMFEMQJJOZGM-RMKNXTFCSA-N 0.000 claims description 6
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 claims description 6
- FCSHDIVRCWTZOX-DVTGEIKXSA-N clobetasol Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O FCSHDIVRCWTZOX-DVTGEIKXSA-N 0.000 claims description 6
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 claims description 6
- WRAABIJFUKKEJQ-UHFFFAOYSA-N cyclopentyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCC1 WRAABIJFUKKEJQ-UHFFFAOYSA-N 0.000 claims description 6
- BTQLDZMOTPTCGG-UHFFFAOYSA-N cyclopentyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCC1 BTQLDZMOTPTCGG-UHFFFAOYSA-N 0.000 claims description 6
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 6
- FKIRSCKRJJUCNI-UHFFFAOYSA-N ethyl 7-bromo-1h-indole-2-carboxylate Chemical compound C1=CC(Br)=C2NC(C(=O)OCC)=CC2=C1 FKIRSCKRJJUCNI-UHFFFAOYSA-N 0.000 claims description 6
- 239000011888 foil Substances 0.000 claims description 6
- DWXAVNJYFLGAEF-UHFFFAOYSA-N furan-2-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CO1 DWXAVNJYFLGAEF-UHFFFAOYSA-N 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 claims description 6
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims description 6
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 claims description 6
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 claims description 6
- FGWRVVZMNXRWDQ-UHFFFAOYSA-N oxan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCO1 FGWRVVZMNXRWDQ-UHFFFAOYSA-N 0.000 claims description 6
- 238000004806 packaging method and process Methods 0.000 claims description 6
- GYDSPAVLTMAXHT-UHFFFAOYSA-N pentyl 2-methylprop-2-enoate Chemical compound CCCCCOC(=O)C(C)=C GYDSPAVLTMAXHT-UHFFFAOYSA-N 0.000 claims description 6
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 6
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 claims description 6
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 claims description 6
- 239000000049 pigment Substances 0.000 claims description 6
- WPBNLDNIZUGLJL-UHFFFAOYSA-N prop-2-ynyl prop-2-enoate Chemical compound C=CC(=O)OCC#C WPBNLDNIZUGLJL-UHFFFAOYSA-N 0.000 claims description 6
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 claims description 6
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 claims description 6
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 6
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 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 claims description 6
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 6
- CXOOGGOQFGCERQ-UHFFFAOYSA-N (2-methyl-2-nitropropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)[N+]([O-])=O CXOOGGOQFGCERQ-UHFFFAOYSA-N 0.000 claims description 5
- FDPPXZRLXIPXJB-UHFFFAOYSA-N (2-methyl-2-nitropropyl) prop-2-enoate Chemical compound [O-][N+](=O)C(C)(C)COC(=O)C=C FDPPXZRLXIPXJB-UHFFFAOYSA-N 0.000 claims description 5
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 claims description 5
- NPYMXLXNEYZTMQ-UHFFFAOYSA-N 3-methoxybutyl prop-2-enoate Chemical compound COC(C)CCOC(=O)C=C NPYMXLXNEYZTMQ-UHFFFAOYSA-N 0.000 claims description 5
- ULYIFEQRRINMJQ-UHFFFAOYSA-N 3-methylbutyl 2-methylprop-2-enoate Chemical compound CC(C)CCOC(=O)C(C)=C ULYIFEQRRINMJQ-UHFFFAOYSA-N 0.000 claims description 5
- YGQURMQHUGDYAO-UHFFFAOYSA-N 4-[2-[2-(4-nitrophenyl)imidazo[2,1-b][1,3]benzothiazol-6-yl]oxyethyl]morpholine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CN2C3=CC=C(OCCN4CCOCC4)C=C3SC2=N1 YGQURMQHUGDYAO-UHFFFAOYSA-N 0.000 claims description 5
- 239000004743 Polypropylene Substances 0.000 claims description 5
- QHGUPRQTQITEPO-UHFFFAOYSA-N oxan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCO1 QHGUPRQTQITEPO-UHFFFAOYSA-N 0.000 claims description 5
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 claims description 5
- 239000003381 stabilizer Substances 0.000 claims description 5
- VBHXIMACZBQHPX-UHFFFAOYSA-N 2,2,2-trifluoroethyl prop-2-enoate Chemical compound FC(F)(F)COC(=O)C=C VBHXIMACZBQHPX-UHFFFAOYSA-N 0.000 claims description 4
- 239000004014 plasticizer Substances 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 229920006267 polyester film Polymers 0.000 claims description 3
- 229920001155 polypropylene Polymers 0.000 claims description 3
- YCYGZZURMBVAGU-UHFFFAOYSA-N C(C(=C)C)(=O)OCCCl.C(C=C)(=O)OCCCl Chemical compound C(C(=C)C)(=O)OCCCl.C(C=C)(=O)OCCCl YCYGZZURMBVAGU-UHFFFAOYSA-N 0.000 claims 2
- 230000006870 function Effects 0.000 abstract description 2
- 238000005286 illumination Methods 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 150000002431 hydrogen Chemical class 0.000 description 16
- 238000001723 curing Methods 0.000 description 13
- 125000000623 heterocyclic group Chemical group 0.000 description 13
- 125000004430 oxygen atom Chemical group O* 0.000 description 11
- 239000000976 ink Substances 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 9
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 9
- 125000004434 sulfur atom Chemical group 0.000 description 9
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- WHBAYNMEIXUTJV-UHFFFAOYSA-N 2-chloroethyl prop-2-enoate Chemical compound ClCCOC(=O)C=C WHBAYNMEIXUTJV-UHFFFAOYSA-N 0.000 description 6
- 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 6
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 6
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 6
- 239000000123 paper Substances 0.000 description 6
- 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 5
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 238000010894 electron beam technology Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 4
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical group OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 description 3
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- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- DDXDGTKWMQZRHH-UHFFFAOYSA-N bis(4-piperazin-1-ylphenyl)methanone Chemical compound C=1C=C(N2CCNCC2)C=CC=1C(=O)C(C=C1)=CC=C1N1CCNCC1 DDXDGTKWMQZRHH-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- LKFAPHHHWRMPGC-UHFFFAOYSA-N butan-1-ol prop-2-enoic acid Chemical compound CCCCO.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C LKFAPHHHWRMPGC-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- RIYWOAMESPSVSB-UHFFFAOYSA-N ethyl n-butylcarbamate;ethyl prop-2-enoate Chemical compound CCOC(=O)C=C.CCCCNC(=O)OCC RIYWOAMESPSVSB-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002192 heptalenyl group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000003427 indacenyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AWJZTPWDQYFQPQ-UHFFFAOYSA-N methyl 2-chloroprop-2-enoate Chemical compound COC(=O)C(Cl)=C AWJZTPWDQYFQPQ-UHFFFAOYSA-N 0.000 description 1
- WFKDPJRCBCBQNT-UHFFFAOYSA-N n,2-dimethylprop-2-enamide Chemical compound CNC(=O)C(C)=C WFKDPJRCBCBQNT-UHFFFAOYSA-N 0.000 description 1
- QRWZCJXEAOZAAW-UHFFFAOYSA-N n,n,2-trimethylprop-2-enamide Chemical compound CN(C)C(=O)C(C)=C QRWZCJXEAOZAAW-UHFFFAOYSA-N 0.000 description 1
- JMCVCHBBHPFWBF-UHFFFAOYSA-N n,n-diethyl-2-methylprop-2-enamide Chemical compound CCN(CC)C(=O)C(C)=C JMCVCHBBHPFWBF-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
- ZIWDVJPPVMGJGR-UHFFFAOYSA-N n-ethyl-2-methylprop-2-enamide Chemical compound CCNC(=O)C(C)=C ZIWDVJPPVMGJGR-UHFFFAOYSA-N 0.000 description 1
- SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical compound CCNC(=O)C=C SWPMNMYLORDLJE-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- 150000002923 oximes Chemical class 0.000 description 1
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- RPDJEKMSFIRVII-UHFFFAOYSA-N oxomethylidenehydrazine Chemical group NN=C=O RPDJEKMSFIRVII-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- UBLMWQYLVOVZMT-UHFFFAOYSA-N tert-butyl n-(3-acetylphenyl)carbamate Chemical compound CC(=O)C1=CC=CC(NC(=O)OC(C)(C)C)=C1 UBLMWQYLVOVZMT-UHFFFAOYSA-N 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical group O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- C08F122/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F122/10—Esters
- C08F122/1006—Esters of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/175—Amines; Quaternary ammonium compounds containing COOH-groups; Esters or salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3462—Six-membered rings
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- 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
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- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
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- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
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- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/103—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
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- Life Sciences & Earth Sciences (AREA)
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Abstract
Description
本願は、2015年1月5日に出願された、その内容を参照によりその全体を本明細書に援用する、米国仮特許出願第62/099,728号の利益を主張するものである。
NCM1は、窒素がベンゾフェノンの第1のフェニル基に共有結合した第1の窒素含有部分であり、
NCM2は、結合、H、又は窒素がベンゾフェノンの第2のフェニル基に共有結合した第2の窒素含有部分であり、
PG1は、アクリラート含有基又はメタクリラート含有基であり、
PG2は、存在しないか、H、アクリラート含有基又はメタクリラート含有基である。
NCM1は、窒素がベンゾフェノンの第1のフェニル基に共有結合した第1の窒素含有部分であり、
NCM2は、結合、H、又は窒素がベンゾフェノンの第2のフェニル基に共有結合した第2の窒素含有部分であり、
PG1は、アクリラート含有基又はメタクリラート含有基であり、
PG2は、存在しないか、H、アクリラート含有基又はメタクリラート含有基である。
NCM1は、窒素がベンゾフェノンの第1のフェニル基に共有結合した第1の窒素含有部分であり、
NCM2は、結合、H、又は窒素がベンゾフェノンの第2のフェニル基に共有結合した第2の窒素含有部分であり、
PG1は、アクリラート含有基又はメタクリラート含有基であり、
PG2は、存在しないか、H、アクリラート含有基又はメタクリラート含有基である。
NCM1は、窒素がベンゾフェノンの第1のフェニル基に共有結合した第1の窒素含有部分であり、
NCM2は、結合、H、又は窒素がベンゾフェノンの第2のフェニル基に共有結合した第2の窒素含有部分であり、
PG1は、アクリラート含有基又はメタクリラート含有基であり、
PG2は、存在しないか、H、アクリラート含有基又はメタクリラート含有基である。
Claims (46)
- ベンゾフェノン部分、前記ベンゾフェノン部分に共有結合した窒素含有部分、及び前記窒素含有部分に共有結合した不飽和重合性部分を含む、光開始剤。
- 前記不飽和重合性部分がアクリラート基又はメタクリラート基を含む、請求項1に記載の光開始剤。
- 前記窒素含有部分が、アゼチジニル、ピロリジニル、ピペラジニル、ピペリジニル、アゼパニル、アゾカニル、又は式−RNR’Hの基であり、Rが、窒素原子を前記ベンゾフェノンに連結するアルキレニル基であり、R’がアルキル基である、請求項1に記載の光開始剤。
- 前記窒素含有部分が、ピペラジニルに基づく部分である、請求項1に記載の光開始剤。
- PG1及びPG2が各々独立にアクリラート含有基又はメタクリラート含有基である、請求項5に記載の光開始剤。
- NCM1とNCM2の少なくとも一方が、アゼチジニル、ピロリジニル、ピペラジニル、ピペリジニル、アゼパニル、アゾカニル、又は式−RNR’Hの基であり、Rが、窒素原子を前記ベンゾフェノンに連結するアルキレニル基であり、R’がアルキル基である、請求項5に記載の光開始剤。
- NCM1とNCM2の少なくとも一方が、ピペラジンに基づく部分である、請求項5に記載の光開始剤。
- PG1及びPG2が各々独立にアクリラート含有基又はメタクリラート含有基である、請求項9に記載の光開始剤。
- PG1及びPG2が個々に、2個以上のアクリラート部分を有するアクリラート含有基、又は2個以上のメタクリラート部分を有するメタクリラート含有基である、請求項5に記載の光開始剤。
- 重合方法であって、
光開始剤と重合組成物を混合して、重合性混合物を形成するステップ、及び
前記重合性混合物に光源からの光を照射するステップ
を含み、
前記重合組成物がアクリラート、メタクリラート又はスチレンモノマーを含み、
前記光開始剤が、
ベンゾフェノン部分、
前記ベンゾフェノン部分に共有結合した窒素含有部分、
及び前記窒素含有部分に共有結合した不飽和重合性部分
を含む、方法。 - 前記光源が可視光源又は紫外線源である、請求項13に記載の方法。
- 前記光源が、発光ダイオード、水銀ランプ、レーザ、又はそれらのいずれか2つ以上の組合せである、請求項13に記載の方法。
- 光硬化性コーティング組成物の硬化方法であって、
前記光硬化性コーティング組成物に発光ダイオードからの光を照射するステップ
を含み、
前記光硬化性コーティング組成物が、
アクリラート、メタクリラート又はスチレンモノマー、及び
光開始剤
を含み、
前記光開始剤が、ベンゾフェノン部分、前記ベンゾフェノン部分に共有結合した窒素含有部分、及び前記窒素含有部分に共有結合した不飽和重合性部分を含む、
方法。 - 前記アクリル、メタクリル又はスチレンモノマーが、アクリル酸、メタクリル酸、メタクリル酸メチル、アクリル酸エチル、メタクリル酸エチル、アクリル酸n−プロピル、メタクリル酸n−プロピル、アクリル酸n−ブチル、メタクリル酸n−ブチル、アクリル酸イソプロピル、メタクリル酸イソプロピル、アクリル酸イソブチル、メタクリル酸イソブチル、アクリル酸n−アミル、メタクリル酸n−アミル、アクリル酸n−ヘキシル、メタクリル酸n−ヘキシル、アクリル酸イソアミル、メタクリル酸イソアミル、アクリル酸トリフルオロエチル、メタクリル酸トリフルオロエチル、アクリル酸ベンジル、メタクリル酸ベンジル、アクリル酸2−n−ブトキシエチル、メタクリル酸2−n−ブトキシエチル、アクリル酸2−クロロエチル、メタクリル酸2−クロロエチル、アクリル酸sec−ブチル、メタクリル酸sec−ブチル、アクリル酸tert−ブチル、メタクリル酸tert−ブチル、アクリル酸2−エチルブチル、メタクリル酸2−エチルブチル、アクリル酸シンナミル、メタクリル酸シンナミル、アクリル酸シクロヘキシル、メタクリル酸シクロヘキシル、アクリル酸シクロペンチル、メタクリル酸シクロペンチル、アクリル酸2−エトキシエチル、メタクリル酸2−エトキシエチル、アクリル酸フルフリル、メタクリル酸フルフリル、アクリル酸ヘキサフルオロイソプロピル、メタクリル酸ヘキサフルオロイソプロピル、アクリル酸3−メトキシブチル、メタクリル酸3−メトキシブチル、アクリル酸2−メトキシブチル、メタクリル酸2−メトキシブチル、アクリル酸2−ニトロ−2−メチルプロピル、メタクリル酸2−ニトロ−2−メチルプロピル、アクリル酸n−オクチル、メタクリル酸n−オクチル、アクリル酸2−エチルヘキシル、メタクリル酸2−エチルヘキシル、アクリル酸2−フェノキシエチル、メタクリル酸2−フェノキシエチル、アクリル酸2−フェニルエチル、メタクリル酸2−フェニルエチル、アクリル酸フェニル、メタクリル酸フェニル、アクリル酸プロパルギル、メタクリル酸プロパルギル、アクリル酸テトラヒドロフルフリル、メタクリル酸テトラヒドロフルフリル、アクリル酸テトラヒドロピラニル、メタクリル酸テトラヒドロピラニル、スチレン又はα−メチルスチレンを含む、請求項13に記載の方法。
- 前記不飽和重合性部分がアクリラート基又はメタクリラート基を含む、請求項13に記載の方法。
- 前記窒素含有部分が、アゼチジニル、ピロリジニル、ピペラジニル、ピペリジニル、アゼパニル、アゾカニル、又は式−RNR’Hの基であり、Rが、窒素原子を前記ベンゾフェノンに連結するアルキレニル基であり、R’がアルキル基である、請求項13に記載の方法。
- 前記窒素含有部分が、ピペラジニルに基づく部分である、請求項13に記載の方法。
- PG1及びPG2が各々独立にアクリラート含有基又はメタクリラート含有基である、請求項21に記載の方法。
- NCM1とNCM2の少なくとも一方が、アゼチジニル、ピロリジニル、ピペラジニル、ピペリジニル、アゼパニル、アゾカニル、又は式−RNR’Hの基であり、Rが、窒素原子を前記ベンゾフェノンに連結するアルキレニル基であり、R’がアルキル基である、請求項21に記載の方法。
- PG1及びPG2が各々独立にアクリラート含有基又はメタクリラート含有基である、請求項24に記載の方法。
- PG1及びPG2が個々に、2個以上のアクリラート部分を有するアクリラート含有基、又は2個以上のメタクリラート部分を有するメタクリラート含有基である、請求項24に記載の方法。
- 前記光硬化性コーティングを硬化前に基板に塗布するステップを更に含む、請求項16に記載の方法。
- 前記基板が紙、アルミ箔、ポリエステルフィルム又はポリプロピレンフィルムを含む、請求項28に記載の方法。
- アクリラート、メタクリラート又はスチレンモノマー、及び
光開始剤
を含み、
前記光開始剤が、ベンゾフェノン部分、前記ベンゾフェノン部分に共有結合した窒素含有部分、及び前記窒素含有部分に共有結合した不飽和重合性部分を含む、
光硬化性組成物。 - 前記アクリル、メタクリル又はスチレンモノマーが、アクリル酸、メタクリル酸、メタクリル酸メチル、アクリル酸エチル、メタクリル酸エチル、アクリル酸n−プロピル、メタクリル酸n−プロピル、アクリル酸n−ブチル、メタクリル酸n−ブチル、アクリル酸イソプロピル、メタクリル酸イソプロピル、アクリル酸イソブチル、メタクリル酸イソブチル、アクリル酸n−アミル、メタクリル酸n−アミル、アクリル酸n−ヘキシル、メタクリル酸n−ヘキシル、アクリル酸イソアミル、メタクリル酸イソアミル、アクリル酸トリフルオロエチル、メタクリル酸トリフルオロエチル、アクリル酸ベンジル、メタクリル酸ベンジル、アクリル酸2−n−ブトキシエチル、メタクリル酸2−n−ブトキシエチル、アクリル酸2−クロロエチル、メタクリル酸2−クロロエチル、アクリル酸sec−ブチル、メタクリル酸sec−ブチル、アクリル酸tert−ブチル、メタクリル酸tert−ブチル、アクリル酸2−エチルブチル、メタクリル酸2−エチルブチル、アクリル酸シンナミル、メタクリル酸シンナミル、アクリル酸シクロヘキシル、メタクリル酸シクロヘキシル、アクリル酸シクロペンチル、メタクリル酸シクロペンチル、アクリル酸2−エトキシエチル、メタクリル酸2−エトキシエチル、アクリル酸フルフリル、メタクリル酸フルフリル、アクリル酸ヘキサフルオロイソプロピル、メタクリル酸ヘキサフルオロイソプロピル、アクリル酸3−メトキシブチル、メタクリル酸3−メトキシブチル、アクリル酸2−メトキシブチル、メタクリル酸2−メトキシブチル、アクリル酸2−ニトロ−2−メチルプロピル、メタクリル酸2−ニトロ−2−メチルプロピル、アクリル酸n−オクチル、メタクリル酸n−オクチル、アクリル酸2−エチルヘキシル、メタクリル酸2−エチルヘキシル、アクリル酸2−フェノキシエチル、メタクリル酸2−フェノキシエチル、アクリル酸2−フェニルエチル、メタクリル酸2−フェニルエチル、アクリル酸フェニル、メタクリル酸フェニル、アクリル酸プロパルギル、メタクリル酸プロパルギル、アクリル酸テトラヒドロフルフリル、メタクリル酸テトラヒドロフルフリル、アクリル酸テトラヒドロピラニル、メタクリル酸テトラヒドロピラニル、スチレン又はα−メチルスチレンを含む、請求項30に記載の光硬化性組成物。
- 前記不飽和重合性部分がアクリラート基又はメタクリラート基を含む、請求項30に記載の光硬化性組成物。
- 前記窒素含有部分が、アゼチジニル、ピロリジニル、ピペラジニル、ピペリジニル、アゼパニル、アゾカニル、又は式−RNR’Hの基であり、Rが、窒素原子を前記ベンゾフェノンに連結するアルキレニル基であり、R’がアルキル基である、請求項30に記載の光硬化性組成物。
- 前記窒素含有部分が、ピペラジニルに基づく部分である、請求項30に記載の光硬化性組成物。
- PG1及びPG2が各々独立にアクリラート含有基又はメタクリラート含有基である、請求項35に記載の光硬化性組成物。
- NCM1とNCM2の少なくとも一方が、アゼチジニル、ピロリジニル、ピペラジニル、ピペリジニル、アゼパニル、アゾカニル、又は式−RNR’Hの基であり、Rが、窒素原子を前記ベンゾフェノンに連結するアルキレニル基であり、R’がアルキル基である、請求項35に記載の光硬化性組成物。
- PG1及びPG2が各々独立にアクリラート含有基又はメタクリラート含有基である、請求項38に記載の光硬化性組成物。
- PG1及びPG2が個々に、2個以上のアクリラート部分を有するアクリラート含有基、又は2個以上のメタクリラート部分を有するメタクリラート含有基である、請求項38に記載の光硬化性組成物。
- 顔料、樹脂、安定剤、可塑剤又は追加の光開始剤の少なくとも1種を更に含む、請求項30に記載の光硬化性組成物。
- コーティング組成物、包装組成物又はインク組成物である、請求項30に記載の光硬化性組成物。
- 請求項44に記載の化合物を含むモノマー単位を含むポリマー。
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KR20170104151A (ko) | 2017-09-14 |
CN107567466A (zh) | 2018-01-09 |
TW201632993A (zh) | 2016-09-16 |
CN107567466B (zh) | 2020-10-09 |
CN110229253A (zh) | 2019-09-13 |
US10584188B2 (en) | 2020-03-10 |
KR20180096821A (ko) | 2018-08-29 |
JP2018510920A (ja) | 2018-04-19 |
WO2016111923A1 (en) | 2016-07-14 |
BR112017014352A2 (pt) | 2018-03-27 |
EP3798238A1 (en) | 2021-03-31 |
JP6576454B2 (ja) | 2019-09-18 |
EP3242898A1 (en) | 2017-11-15 |
JP6771626B2 (ja) | 2020-10-21 |
EP3242898A4 (en) | 2018-10-24 |
US20190233550A1 (en) | 2019-08-01 |
US20180016364A1 (en) | 2018-01-18 |
CN110229253B (zh) | 2021-11-02 |
KR101921013B1 (ko) | 2018-11-21 |
KR101942698B1 (ko) | 2019-01-25 |
US10301399B2 (en) | 2019-05-28 |
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