JP6273759B2 - 光硬化性組成物 - Google Patents
光硬化性組成物 Download PDFInfo
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- JP6273759B2 JP6273759B2 JP2013216732A JP2013216732A JP6273759B2 JP 6273759 B2 JP6273759 B2 JP 6273759B2 JP 2013216732 A JP2013216732 A JP 2013216732A JP 2013216732 A JP2013216732 A JP 2013216732A JP 6273759 B2 JP6273759 B2 JP 6273759B2
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- Prior art keywords
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- meth
- ethyl
- acrylate
- compound
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- 239000000203 mixture Substances 0.000 title claims description 67
- 150000001875 compounds Chemical class 0.000 claims description 60
- -1 oxetane compound Chemical class 0.000 claims description 60
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 46
- 239000004593 Epoxy Substances 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000003700 epoxy group Chemical group 0.000 claims description 13
- 239000003505 polymerization initiator Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 229920000058 polyacrylate Polymers 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 7
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 claims description 7
- 125000002091 cationic group Chemical group 0.000 claims description 5
- 150000001768 cations Chemical group 0.000 claims description 5
- 238000012663 cationic photopolymerization Methods 0.000 claims description 4
- 125000003566 oxetanyl group Chemical group 0.000 claims description 4
- 125000000129 anionic group Chemical group 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 47
- 229920000642 polymer Polymers 0.000 description 39
- 239000000178 monomer Substances 0.000 description 30
- 238000001723 curing Methods 0.000 description 28
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 21
- 239000000853 adhesive Substances 0.000 description 19
- 230000001070 adhesive effect Effects 0.000 description 19
- 125000001931 aliphatic group Chemical group 0.000 description 18
- 238000000034 method Methods 0.000 description 17
- 239000000126 substance Substances 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 238000013329 compounding Methods 0.000 description 15
- FNYWFRSQRHGKJT-UHFFFAOYSA-N 3-ethyl-3-[(3-ethyloxetan-3-yl)methoxymethyl]oxetane Chemical compound C1OCC1(CC)COCC1(CC)COC1 FNYWFRSQRHGKJT-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 125000002723 alicyclic group Chemical group 0.000 description 14
- 238000010526 radical polymerization reaction Methods 0.000 description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 13
- 229920002554 vinyl polymer Polymers 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 150000004756 silanes Chemical class 0.000 description 11
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 239000011574 phosphorus Substances 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- 150000005846 sugar alcohols Polymers 0.000 description 8
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 7
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 229920000620 organic polymer Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000011417 postcuring Methods 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 229910001507 metal halide Inorganic materials 0.000 description 4
- 150000005309 metal halides Chemical class 0.000 description 4
- 150000002921 oxetanes Chemical class 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 230000000979 retarding effect Effects 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- BIDWUUDRRVHZLQ-UHFFFAOYSA-N 3-ethyl-3-(2-ethylhexoxymethyl)oxetane Chemical compound CCCCC(CC)COCC1(CC)COC1 BIDWUUDRRVHZLQ-UHFFFAOYSA-N 0.000 description 3
- LMIOYAVXLAOXJI-UHFFFAOYSA-N 3-ethyl-3-[[4-[(3-ethyloxetan-3-yl)methoxymethyl]phenyl]methoxymethyl]oxetane Chemical compound C=1C=C(COCC2(CC)COC2)C=CC=1COCC1(CC)COC1 LMIOYAVXLAOXJI-UHFFFAOYSA-N 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 3
- 239000004843 novolac epoxy resin Substances 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 239000003566 sealing material Substances 0.000 description 3
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- JUXZNIDKDPLYBY-UHFFFAOYSA-N 3-ethyl-3-(phenoxymethyl)oxetane Chemical compound C=1C=CC=CC=1OCC1(CC)COC1 JUXZNIDKDPLYBY-UHFFFAOYSA-N 0.000 description 2
- UWFHYGTWXNRUDH-UHFFFAOYSA-N 3-ethyl-3-[4-[(3-ethyloxetan-3-yl)methoxy]butoxymethyl]oxetane Chemical compound C1OCC1(CC)COCCCCOCC1(CC)COC1 UWFHYGTWXNRUDH-UHFFFAOYSA-N 0.000 description 2
- XJMMNTGIMDZPMU-UHFFFAOYSA-N 3-methylglutaric acid Chemical compound OC(=O)CC(C)CC(O)=O XJMMNTGIMDZPMU-UHFFFAOYSA-N 0.000 description 2
- RBMGGZPJAZDWNE-UHFFFAOYSA-N 4-[(3-ethyloxetan-3-yl)methoxy]butan-1-ol Chemical compound OCCCCOCC1(CC)COC1 RBMGGZPJAZDWNE-UHFFFAOYSA-N 0.000 description 2
- CNSJBIWGZMUGKY-UHFFFAOYSA-N 4-methoxy-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(OC)CCC2OC21 CNSJBIWGZMUGKY-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- PWHYOGRKVRMWLT-UHFFFAOYSA-H [F-].[F-].[F-].[F-].[F-].[F-].C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1 Chemical compound [F-].[F-].[F-].[F-].[F-].[F-].C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1 PWHYOGRKVRMWLT-UHFFFAOYSA-H 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
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- 238000004458 analytical method Methods 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 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
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-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
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 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
- 229950000688 phenothiazine Drugs 0.000 description 1
- LYKRPDCJKSXAHS-UHFFFAOYSA-N phenyl-(2,3,4,5-tetrahydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC(C(=O)C=2C=CC=CC=2)=C1O LYKRPDCJKSXAHS-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- NECLQTPQJZSWOE-UHFFFAOYSA-N spiro[5.5]undecane Chemical compound C1CCCCC21CCCCC2 NECLQTPQJZSWOE-UHFFFAOYSA-N 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- IDYFACFOJYNFAX-UHFFFAOYSA-J tetrafluoroantimony Chemical compound F[Sb](F)(F)F IDYFACFOJYNFAX-UHFFFAOYSA-J 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- WUMSTCDLAYQDNO-UHFFFAOYSA-N triethoxy(hexyl)silane Chemical compound CCCCCC[Si](OCC)(OCC)OCC WUMSTCDLAYQDNO-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- UZIAQVMNAXPCJQ-UHFFFAOYSA-N triethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)COC(=O)C(C)=C UZIAQVMNAXPCJQ-UHFFFAOYSA-N 0.000 description 1
- QYBKVVRRGQSGDC-UHFFFAOYSA-N triethyl methyl silicate Chemical compound CCO[Si](OC)(OCC)OCC QYBKVVRRGQSGDC-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- UOKUUKOEIMCYAI-UHFFFAOYSA-N trimethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C(C)=C UOKUUKOEIMCYAI-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- VBEKPAAWUSCJSK-UHFFFAOYSA-H triphenylsulfanium hexafluoride Chemical compound [F-].[F-].[F-].[F-].[F-].[F-].C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1 VBEKPAAWUSCJSK-UHFFFAOYSA-H 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical class C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polyethers (AREA)
- Epoxy Resins (AREA)
Description
本発明において、前記(B)エポキシ化合物及び前記(C)オキセタン化合物を組み合わせて用いることにより、貼り合わせ可能時間が充分長く、接着強度発現までの時間が短く、しっかり固まる、といった効果が達成される。
原子移動ラジカル重合において用いられる(メタ)アクリル系モノマーやビニル系モノマーとしては特に制約はなく、例示した(メタ)アクリル系モノマーやビニル系モノマーをすべて好適に用いることができる。
1,2,3−プロパントリカルボン酸、1,2,3,4−ブタンテトラカルボン酸、1,2,3,4−シクロブタンテトラカルボン酸などが挙げられる。
前記(B)エポキシ化合物の配合割合は特に制限はないが、(A)重合体100質量部に対して、1〜150質量部が好ましく、10〜100質量部がより好ましく、30〜80質量部がさらに好ましい。
前記(C)オキセタン化合物の配合割合は特に制限はないが、(A)重合体100質量部に対して、1〜100質量部が好ましく、2〜60質量部がより好ましく、5〜40質量部がさらに好ましい。
前記他のオキセタン化合物としては、例えば、(3−エチル−3−オキセタニルメトキシ)メチルベンゼン,[1−(3−エチル−3−オキセタニルメトキシ)エチル]フェニルエーテル,イソブトキシメチル(3−エチル−3−オキセタニルメチル)エーテル,イソボルニルオキシエチル(3−エチル−3−オキセタニルメチル)エーテル,イソボルニル(3−エチル−3−オキセタニルメチル)エーテル,2−エチルヘキシル(3−エチル−3−オキセタニルメチル)エーテル,エチルジエチレングリコール(3−エチル−3−オキセタニルメチル)エーテル,ジシクロペンテニルオキシエチル(3−エチル−3−オキセタニルメチル)エーテル,ジシクロペンテニル(3−エチル−3−オキセタニルメチル)エーテル,テトラブロモフェニル(3−エチル−3−オキセタニルメチル)エーテル,2−テトラブロモフェノキシエチル(3−エチル−3−オキセタニルメチル)エーテル,トリブロモフェニル(3−エチル−3−オキセタニルメチル)エーテル,2−トリブロモフェノキシエチル(3−エチル−3−オキセタニルメチル)エーテル,ブトキシエチル(3−エチル−3−オキセタニルメチル)エーテル,ペンタクロロフェニル(3−エチル−3−オキセタニルメチル)エーテル,ペンタブロモフェニル(3−エチル−3−オキセタニルメチル)エーテル,ボルニル(3−エチル−3−オキセタニルメチル)エーテル,3,7−ビス(3−オキセタニル)−5−オキサ−ノナン,3,3’−(1,3−(2−メチレニル)プロパンジイルビス(オキシメチレン))ビス−(3−エチルオキセタン),1,4−ビス[(3−エチル−3−オキセタニルメトキシ)メチル]ベンゼン,1,2−ビス[(3−エチル−3−オキセタニルメトキシ)メチル]エタン,1,3−ビス[(3−エチル−3−オキセタニルメトキシ)メチル]プロパン,エチレングリコールビス(3−エチル−3−オキセタニルメチル)エーテル,ジシクロペンテニルビス(3−エチル−3−オキセタニルメチル)エーテル,トリエチレングリコールビス(3−エチル−3−オキセタニルメチル)エーテル,テトラエチレングリコールビス(3−エチル−3−オキセタニルメチル)エーテル,トリシクロデカンジイルジメチレン(3−エチル−3−オキセタニルメチル)エーテル,トリメチロールプロパントリス(3−エチル−3−オキセタニルメチル)エーテル,1,4−ビス(3−エチル−3−オキセタニルメトキシ)ブタン,1,6−ビス(3−エチル−3−オキセタニルメトキシ)ヘキサン,ペンタエリスリトールトリス(3−エチル−3−オキセタニルメチル)エーテル,ペンタエリスリトールテトラキス(3−エチル−3−オキセタニルメチル)エーテル,ポリエチレングリコールビス(3−エチル−3−オキセタニルメチル)エーテル,ジペンタエリスリトールヘキサキス(3−エチル−3−オキセタニルメチル)エーテル,ジペンタエリスリトールペンタキス(3−エチル−3−オキセタニルメチル)エーテル,ジペンタエリスリトールテトラキス(3−エチル−3−オキセタニルメチル)エーテル,3−エチル−3−フェノキシメチルオキセタン,3−エチル−3−(4−メチルフェノキシ)メチルオキセタン,3−エチル−3−(4−フルオロフェノキシ)メチルオキセタン,3−エチル−3−(1−ナフトキシ)メチルオキセタン,3−エチル−3−(2−ナフトキシ)メチルオキセタン,3−エチル−3−{[3−(エトキシシリル)プロポキシ]メチル}オキセタン,オキセタニルシルセスキオキセタン及びフェノールノボラックオキセタン等が挙げられる。
前記(D)光カチオン重合開始剤の配合割合は特に制限はないが、(A)重合体100質量部に対して、0.1〜50質量部が好ましく、0.3〜30質量部がより好ましく、0.5〜20質量部がさらに好ましい。
なお、本発明の光硬化性組成物は、光酸発生剤等の(D)光カチオン重合開始剤を用いて(A)重合体を架橋させ、硬化せしめる為、アミン化合物等の塩基性化合物は硬化性や触媒能を低下させるおそれがある。よって、本発明の光硬化性組成物に塩基性化合物を配合する場合は、本発明の効果を阻害しない範囲で配合することが好適である。
LA−57,MARK LA−62,MARK LA−63,MARK LA−67,MARK LA−68(以上、いずれも株式会社ADEKA製);サノールLS−770,サノールLS−765,サノールLS−292,サノールLS−2626,サノールLS−1114,サノールLS−744(以上、いずれもBASF社製)に示されたヒンダードアミン系光安定剤を使用することもできる。酸化防止剤の具体例は、特開平4−283259号公報や特開平9−194731号公報にも記載されている。
末端にハロゲンを有するポリ(アクリル酸n−ブチル)の合成(原子移動ラジカル重合法)
50mlフラスコに臭化第一銅0.63g(4.4mmol)、ペンタメチルジエチレントリアミン0.76g(4.4mmol)、アセトニトリル5ml、2,5−ジブロモアジピン酸ジエチル1.6g(4.4mmol)、アクリル酸n−ブチル44.7g(349mmol)を仕込み、凍結脱気をおこなった後、窒素雰囲気下で70℃7時間反応させた。活性アルミナのカラムを通して銅触媒を除去精製することにより末端にBr基を有するポリ(アクリル酸n−ブチル)を得た。得られた重合体の数平均分子量は10700、分子量分布1.15であった。
窒素雰囲気下、200mlフラスコに上記で得た末端にBr基を有するポリ(アクリル酸n−ブチル)35g、ペンテン酸カリウム2.2g(16.1mmol)、DMAc35mLを仕込み、70℃で4時間反応させた。反応混合液中の未反応のペンテン酸カリウムおよび生成した臭化カリウムを水抽出精製により除去し、末端にアルケニル基を有するポリ(アクリル酸n−ブチル)を得た。得られた重合体の数平均分子量は11300、分子量分布1.12であった。また1H−NMR分析より求めた重合体1分子あたりのアルケニル基の個数は1.82個であった。
200mL耐圧反応管に上記で得た末端にアルケニル基を有するポリ(アクリル酸n−ブチル)15g、メチルジメトキシシラン1.8mL(14.5mmol)、オルトギ酸メチル0.26mL(2.4mmol)、白金ビス(ジビニルテトラメチルジシロキサン)10-4mmolを仕込み、100℃で4時間反応させ、末端にメチルジメトキシシリル基を有するポリ(アクリル酸n−ブチル)A1(以下、アクリル系重合体A1と称する)を得た。得られた重合体の粘度は44Pa・sであり、数平均分子量は11900、分子量分布1.12であった。また1H−NMR分析により重合体1分子あたりのメチルジメトキシシリル基の個数は1.46個であった。
表1に示す配合割合にて、攪拌機、温度計、窒素導入口、モノマー装入管および水冷コンデンサーを装着した300mLのフラスコに、合成例1で得たアクリル系重合体A1、及びYX8000[三菱化学社製、水添ビスフェノールA型エポキシ樹脂]、を混合した。該混合物を加熱(100℃)、脱気、撹拌を2時間することによって混練及び脱水をした。冷却後、その混合物にEHO(3−エチル−3−ヒドロキシメチルオキセタン)、CPI−200K[サンアプロ社製、光酸発生剤]、及び微粉末シリカ、をそれぞれ添加し、混合撹拌することにより光硬化性組成物を調製した。
YX8000;三菱化学社製、水添ビスフェノールA型エポキシ樹脂(官能基数:2個、エポキシ当量:205)
EHO;3−エチル−3−ヒドロキシメチルオキセタン、宇部興産社製、商品名:エタナコールEHO。
CPI−200K;サンアプロ社製、光酸発生剤[トリス(フルオロエチル)トリフルオロホスフェートのスルホニウム塩]。
微粉末シリカ;東ソー社製、商品名:ニプシルLP。
1)可使時間の試験方法
ステンレス板(25mm×100mm×1.5mm)上に光硬化性組成物を約50μm厚に塗布し、UV照射[照射条件:メタルハライドランプ(照度50mW/cm2)、積算光量:200mJ/cm2]し、23℃50%RH、照度550ルクス(蛍光灯)の条件で静置する。UV照射後、指触により試料の流動性がなくなるまでに要した時間を測定した。
ステンレス板(25mm×100mm×1.5mm)上に光硬化性組成物を約50μm厚に塗布し、UV照射[照射条件:メタルハライドランプ(照度50mW/cm2)、積算光量:200mJ/cm2]する。23℃50%RHの環境下、UV照射後直ちに、同じ大きさのステンレス板の中央部と重ねて十字になるように貼り合わせ、手で動かなくなるまでの時間を測定した。
前記可使時間が30秒以上、かつ、前記初期接着強度発現時間が前記可使時間の3倍以下の場合は○と評価する。前記可使時間が30秒未満である場合、又は前記初期接着強度発現時間が前記可使時間の3倍を超える場合は×と評価する。
フロートガラス(5×50×50mm)上に光硬化性組成物を120μm厚に塗布し、UV照射[照射条件:メタルハライドランプ(照度:50mW/cm2)、積算光量:200mJ/cm2]する。照射後すぐに、光硬化性組成物の厚みが100μmになるように、アルミニウム板(5×50×50mm)を貼り合せる。23℃50%RHにて1週間養生し、試験体を作製する。
二つのビーカーを用意し、第一のビーカー内に煮沸水を用意する。第二のビーカー内にメタノールを用意し、−20℃になるようにドライアイスを用いて温度調整する。試験体を第一のビーカーに5分間浸漬させる。取り出し後すぐに第二のビーカーに5分間浸漬させ、下記評価を行った。
ガラスが割れなかった場合もしくは被着体が剥がれなかった場合は、光硬化性組成物の硬化物が被着体の熱収縮に追従するのに十分な柔軟な硬化皮膜を有すると判断し、〇と評価する。ガラスが割れた場合もしくは被着体が剥がれた場合、光硬化性組成物の硬化物が被着体の熱収縮に追従できなかった、もしくは内部応力を緩和できなかったとして、×と評価する。
28℃70%RH環境下における初期接着強度発現時間を、23℃50%RH環境下における初期接着強度発現時間で割ることにより算出した。
表1に示した如く配合物質を変更した以外は実施例1と同様の方法により光硬化性組成物を調製した。該光硬化性組成物の可使時間、初期接着強度発現時間、後硬化性、被膜物性、及び遅延倍率の各試験を実施例1と同様の方法により行い、その結果を表1に示した。
表2に示した如く配合物質を変更した以外は実施例1と同様の方法により光硬化性組成物を調製した。該光硬化性組成物の可使時間、初期接着強度発現時間、後硬化性、被膜物性、及び遅延倍率の各試験を実施例1と同様の方法により行い、その結果を表2に示した。
#828:三菱化学(株)製、商品名JER828、ビスフェノールA型エポキシ樹脂、官能基数:2、エポキシ当量:184〜194。
CPI−100P:サンアプロ(株)製の商品名、光酸発生剤、ジフェニル−4−(フェニルチオ)フェニルスルホニウムヘキサフルオロホスフェート。
IK−1:サンアプロ(株)製、光酸発生剤、アニオン部分が特殊リン系のヨードニウム塩。
イルガキュア250:BASF社製、光酸発生剤、((4−メチルフェニル)[4−(2−メチルプロピル)フェニル]ヨードニウム−ヘキサフルオロフォスフェートとプロピレンカーボネート溶剤との3:1の混合物。
表3に示した如く配合物質を変更した以外は実施例1と同様の方法により光硬化性組成物を調製した。該光硬化性組成物の可使時間、初期接着強度発現時間、後硬化性、被膜物性、及び遅延倍率の各試験を実施例1と同様の方法により行い、その結果を表3に示した。
OXT−121;東亞合成社製、キシリレンビスオキセタン。
OXT−212;東亞合成社製、2−エチルヘキシルオキセタン。
OXT−221;東亞合成社製、3−エチル−3{[(3−エチルオキセタン−3−イル)メトキシ]メチル}オキセタン。
IPA:イソプロピルアルコール。
さらに、光カチオン重合開始剤としてカチオン部分が芳香族ヨードニウムの光カチオン重合開始剤を用いると、高湿雰囲気下においても十分な硬化速度が得られることが確認された。
Claims (2)
- (A)架橋性珪素基含有(メタ)アクリル系重合体、
(B)分子内に少なくとも2個のエポキシ基を有するエポキシ化合物、
(C)水酸基と1個のオキセタニル基とを有するオキセタン化合物、及び
(D)カチオン部分が芳香族ヨードニウムである光カチオン重合開始剤
を含有する、光硬化性組成物。 - 前記(D)カチオン部分が芳香族ヨードニウムである光カチオン重合開始剤のアニオン部分がPF6 −である、請求項1記載の光硬化性組成物。
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