CN113557277B - Curable resin composition, cured product, and electronic component - Google Patents
Curable resin composition, cured product, and electronic component Download PDFInfo
- Publication number
- CN113557277B CN113557277B CN202080020648.9A CN202080020648A CN113557277B CN 113557277 B CN113557277 B CN 113557277B CN 202080020648 A CN202080020648 A CN 202080020648A CN 113557277 B CN113557277 B CN 113557277B
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- China
- Prior art keywords
- curable resin
- meth
- resin composition
- acrylate
- compound
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 148
- 229920005989 resin Polymers 0.000 claims abstract description 52
- 239000011347 resin Substances 0.000 claims abstract description 52
- 238000003860 storage Methods 0.000 claims abstract description 40
- 150000001875 compounds Chemical class 0.000 claims description 131
- -1 acrylic compound Chemical class 0.000 claims description 124
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 27
- 125000002723 alicyclic group Chemical group 0.000 claims description 20
- 239000003431 cross linking reagent Substances 0.000 claims description 20
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 18
- 230000015572 biosynthetic process Effects 0.000 claims description 15
- 229920001519 homopolymer Polymers 0.000 claims description 13
- 239000003999 initiator Substances 0.000 claims description 11
- 230000009477 glass transition Effects 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 143
- 230000001070 adhesive effect Effects 0.000 description 36
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 34
- 229920005862 polyol Polymers 0.000 description 29
- 239000000853 adhesive Substances 0.000 description 27
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 26
- 239000005056 polyisocyanate Substances 0.000 description 22
- 229920001228 polyisocyanate Polymers 0.000 description 22
- 239000003822 epoxy resin Substances 0.000 description 20
- 229920000647 polyepoxide Polymers 0.000 description 20
- 238000000034 method Methods 0.000 description 19
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 16
- 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 16
- 150000003077 polyols Chemical class 0.000 description 16
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 15
- 239000011521 glass Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 239000007822 coupling agent Substances 0.000 description 12
- 239000000945 filler Substances 0.000 description 11
- 239000004593 Epoxy Substances 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000004417 polycarbonate Substances 0.000 description 8
- 229920000515 polycarbonate Polymers 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
- 239000006087 Silane Coupling Agent Substances 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 229920000570 polyether Polymers 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000000016 photochemical curing Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000002194 synthesizing effect Effects 0.000 description 6
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- 229930185605 Bisphenol Natural products 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- 229920000620 organic polymer Polymers 0.000 description 5
- 229920005906 polyester polyol Polymers 0.000 description 5
- 229960004063 propylene glycol Drugs 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 229920001187 thermosetting polymer Polymers 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 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 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 4
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 3
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Chemical group 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 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 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 3
- 238000013008 moisture curing Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920005749 polyurethane resin Polymers 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- LAIJAUHBAWLPCO-UHFFFAOYSA-N (4-tert-butylcyclohexyl) prop-2-enoate Chemical compound CC(C)(C)C1CCC(OC(=O)C=C)CC1 LAIJAUHBAWLPCO-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 description 2
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HNUKTDKISXPDPA-UHFFFAOYSA-N 2-oxopropyl Chemical group [CH2]C(C)=O HNUKTDKISXPDPA-UHFFFAOYSA-N 0.000 description 2
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- MBXULDRFQBQSSK-UHFFFAOYSA-N N'-[3-[methoxy-[(2-methylpropan-2-yl)oxy]silyl]propyl]ethane-1,2-diamine Chemical compound NCCNCCC[SiH](OC(C)(C)C)OC MBXULDRFQBQSSK-UHFFFAOYSA-N 0.000 description 2
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- YPCHGLDQZXOZFW-UHFFFAOYSA-N [2-[[4-methyl-3-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]carbonylamino]phenyl]carbamoyloxymethyl]-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound CC1=CC=C(NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)C=C1NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C YPCHGLDQZXOZFW-UHFFFAOYSA-N 0.000 description 2
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 230000005540 biological transmission Effects 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
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- 238000000576 coating method Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 2
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- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 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 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
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- 229920000909 polytetrahydrofuran Polymers 0.000 description 2
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- 239000004814 polyurethane Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
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- 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
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 1
- DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- RFJIPESEZTVQHZ-UHFFFAOYSA-N oxirane;prop-2-enoic acid Chemical compound C1CO1.OC(=O)C=C RFJIPESEZTVQHZ-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
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- QLNOVKKVHFRGMA-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical group [CH2]CC[Si](OC)(OC)OC QLNOVKKVHFRGMA-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
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- AMJYHMCHKZQLAY-UHFFFAOYSA-N tris(2-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound O=C=NC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)N=C=O)OC1=CC=CC=C1N=C=O AMJYHMCHKZQLAY-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/302—Water
- C08G18/307—Atmospheric humidity
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—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 C09J159/00 - C09J187/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The curable resin composition of the present invention is a curable resin composition containing a moisture-curable resin (A), wherein the cured product of the curable resin composition has a storage modulus of 10MPa or more at 25 ℃ and an elongation at break of 700% or more at 25 ℃.
Description
Technical Field
The present invention relates to a curable resin composition, a cured product of the curable resin composition, and an electronic component including the cured product of the curable resin composition.
Background
In recent years, high integration and miniaturization have been demanded for electronic parts such as semiconductor chips, and for example, a laminate of a plurality of thin semiconductor chips is often produced by bonding a plurality of thin semiconductor chips via an adhesive layer. In addition, in modern times in which various portable devices having display units are popular, as a method for miniaturizing the display units, narrowing of the image display unit (hereinafter, also referred to as "narrow-edge design") is performed. In the narrow edge design, a technology of bonding by using an adhesive having a relatively thin line width such as a dispenser is required.
In the bonding of these small electronic parts and narrow edge design, high bonding strength is generally required, and therefore, the use of moisture-curable adhesives has been studied. As a moisture-curable adhesive having improved adhesive strength, for example, patent document 1 discloses a moisture-curable polyurethane hot-melt resin composition comprising: a urethane prepolymer having an isocyanate group, an acrylic polymer, a thermoplastic resin having a softening temperature in the range of 50 to 80 ℃, and a curing catalyst.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open publication 2016-113552
Disclosure of Invention
[ problem to be solved by the invention ]
In addition to high adhesive strength, high impact absorbability is required in order to prevent the transmission of impact to electronic parts in the adhesion or narrow edge design of small electronic parts. However, the moisture-curable resin composition disclosed in patent document 1 is difficult to sufficiently improve the adhesive strength and impact resistance.
Accordingly, an object of the present invention is to provide a curable resin composition having excellent adhesive strength and impact resistance.
[ means for solving the problems ]
As a result of diligent studies, the present inventors have found that the above problems can be solved by setting both storage modulus and elongation at break at 25 ℃ of a cured product to specific values or more in a curable resin composition containing a moisture curable resin, and have completed the present invention as follows. That is, the present invention provides the following (1) to (13).
(1) A curable resin composition comprising a moisture-curable resin (A),
the cured product of the curable resin composition has a storage modulus of 10MPa or more at 25 ℃ and an elongation at break of 700% or more at 25 ℃.
(2) The curable resin composition according to (1) above, further comprising a crosslinking agent (X), wherein the content of the crosslinking agent (X) is 0.4 mass% or more and 10 mass% or less based on the total amount of the curable resin composition.
(3) The curable resin composition according to (2) above, wherein the crosslinking agent (X) is a compound having an isocyanate group.
(4) The curable resin composition according to any one of (1) to (3), further comprising a photopolymerizable compound B and a photopolymerization initiator (Y).
(5) The curable resin composition according to (4) above, wherein the photopolymerizable compound B contains a compound B1, and the glass transition temperature (Tg) of the compound B1 after formation of a homopolymer is 70℃or higher.
(6) The curable resin composition according to (5) above, wherein the content of the compound B1 is 10% by mass or more and 50% by mass or less based on the total amount of the photopolymerizable compounds B.
(7) The curable resin composition according to (5) or (6), wherein the content of the compound B1 is 2.5% by mass or more and 15% by mass or less based on the total amount of the curable resin composition.
(8) The curable resin composition according to any one of (4) to (7), wherein the photopolymerizable compound B comprises a (meth) acrylic compound having an alicyclic structure.
(9) The curable resin composition according to any one of (4) to (8), wherein the photopolymerizable compound B contains a compound B2, and the glass transition temperature (Tg) of the compound B2 after formation of a homopolymer is lower than 70 ℃.
(10) The curable resin composition according to any one of (1) to (9), wherein the moisture-curable resin (A) is a moisture-curable urethane resin.
(11) The curable resin composition according to any one of (1) to (10), wherein the moisture-curable resin (A) is contained in an amount of 50 to 80 mass% based on the total amount of the curable resin composition.
(12) A cured product of the curable resin composition according to any one of the above (1) to (11).
(13) An electronic component comprising the cured product of (12).
[ Effect of the invention ]
The present invention provides a curable resin composition having excellent adhesive strength and impact resistance.
Drawings
FIG. 1 is a schematic diagram for explaining a measurement method of PUSH adhesive force.
FIG. 2 is a schematic diagram for explaining an evaluation method of impact resistance.
Detailed Description
The present invention will be described in detail below.
[ curable resin composition ]
The curable resin composition of the present invention is a curable resin composition containing a moisture-curable resin, wherein the cured product of the curable resin composition has a storage modulus of 10MPa or more at 25 ℃ and an elongation at break of 700% or more at 25 ℃.
The curable resin composition of the present invention has both the storage modulus and the elongation at break of the cured product improved as described above, and thus has high adhesive strength, particularly high PUSH adhesive strength, and excellent impact resistance. Therefore, when the adherend is bonded with the curable resin composition of the present invention, even when the bonding area is small or the application width is small, for example, peeling of the adherend can be prevented when a strong impact is applied, and the impact can be prevented from being transmitted to the electronic component.
On the other hand, if the cured product of the curable resin composition has a storage modulus of less than 10MPa at 25 ℃ or an elongation at break of less than 700% at 25 ℃, it is difficult to achieve both excellent adhesion performance and impact resistance, and if an impact is applied, the adherend peels off or the impact is transmitted to an electronic component.
From the viewpoint of stably improving both the adhesive property and the impact resistance, the storage modulus of the cured product at 25℃is preferably 16MPa or more, more preferably 20MPa or more. In addition, the storage modulus at 25 ℃ is, for example, 75MPa or less, preferably 45MPa or less, from the viewpoint of easily securing a high elongation at break, and more preferably 32MPa or less from the viewpoint of further improving the adhesion.
In addition, from the viewpoint of stably improving both the adhesiveness and the impact resistance, the elongation at break is preferably 750% or more, more preferably 800% or more, still more preferably 850% or more. In addition, from the viewpoint of ensuring a high storage modulus of the cured product, the elongation at break is, for example, 1500% or less, preferably 1000% or less.
In the present invention, the storage modulus of the cured product is measured by the following method.
The curable resin composition was poured into a teflon (registered trademark) mold having a width of 3mm, a length of 30mm, and a thickness of 1mm, and cured, whereby a cured product sample was obtained. Using the obtained cured product sample, dynamic viscoelasticity was measured in a range of 40 to 150℃by a dynamic viscoelasticity measuring device, and the storage modulus at 25℃was obtained. Furthermore, the measurement conditions were: stretching in a deformation mode, setting the strain to be 1%, measuring the frequency to be 1Hz, and heating the temperature to be 5 ℃/min.
The elongation at break of the cured product was measured by the following method. The curable resin composition was poured into a dumbbell-shaped (JISK 6251-specified No. 6 mold) silicone rubber mold with holes, and cured, thereby obtaining a dumbbell-shaped test piece of No. 6 mold. The obtained test piece was stretched at a stretching speed of 50 mm/min by using a tensile tester, and the elongation at break at 25℃was measured.
The curable resin composition used to obtain the cured product sample may be cured as long as the curable resin composition is entirely curable, and may be cured by the following method according to its curing mechanism. For example, in the case of photo-moisture curability, the following procedure is used: irradiation with UV-LEDs (wavelength 365 nm) 1000mJ/cm 2 Thereby photo-curing it, and then, it was left to stand at 23℃for 24 hours under 50% RH to cure it with moisture. In addition, in the case of moisture curability, the process is performed in the same manner as described above, except that the step of photo-curing is omitted.
In the case of the heat-and moisture-curable resin composition, the following procedure is carried out: heating at 90℃for 2 hours, followed by 2It was allowed to stand at 3℃under 50% RH for 24 hours to cure it with moisture. In the case of the light, heat, and moisture curable resin composition, it can be carried out in the following manner: irradiation with UV-LEDs (wavelength 365 nm) 1000mJ/cm 2 Thereby photo-curing it, followed by heating at 90 ℃ for 2 hours to thermally cure it, and then leaving it to stand at 23 ℃ for 24 hours in an environment of 50% rh to moisture cure it.
The curable resin composition of the present invention is a moisture-curable resin composition having at least the moisture-curable resin (a) as described above. If the curable resin composition is moisture-curable, the adhesion is easily improved. The curable resin composition of the present invention preferably contains, in addition to the moisture-curable resin (a), at least one of a photopolymerizable compound B (photocurable resin) that is cured by irradiation with light and a thermosetting resin (C) that is cured by heating.
Here, when the photopolymerizable compound B is further contained in the curable resin composition in addition to the moisture curable resin (a), the curable resin composition becomes a photo moisture curable resin composition cured by irradiation with light and moisture. When the curable resin composition further contains a thermosetting resin (C) in addition to the moisture-curable resin (a), the curable resin composition becomes a thermal moisture-curable resin composition cured by heating and moisture. Further, when the curable resin composition contains the photopolymerizable compound B and the thermosetting resin (C) in addition to the moisture-curable resin (a), the curable resin composition becomes a light, heat and moisture-curable resin composition that is cured by light irradiation, heat and moisture.
The curable resin composition preferably contains a moisture-curable resin (a) and a photopolymerizable compound B. That is, the curable resin composition is preferably a photo-moisture curable resin composition. The photo-moisture curable resin composition has excellent adhesion performance even when cured without heating, and therefore, it is possible to prevent damage to the adhesive portion or electronic parts around the adhesive portion due to heating and the like when the curable resin composition is cured, and it is possible to make the adhesion performance excellent.
The photo moisture curable resin composition is cured by, for example, first, photo curing to form a B-stage state, imparting relatively low adhesion (tackiness), and then further curing by moisture in the air or the like, whereby a cured product having sufficiently high adhesion can be formed.
Hereinafter, each detailed component when the curable resin composition of the present invention contains the moisture curable resin (a) and the photopolymerizable compound B and is the photo moisture curable resin composition will be described.
(moisture-curable resin (A))
Examples of the moisture-curable resin (a) used in the present invention include moisture-curable urethane resins, hydrolyzable silicon group-containing resins, and moisture-curable cyanoacrylate resins. Among these, the moisture-curable urethane resin and the resin containing a hydrolyzable silicon group are preferable, and the moisture-curable urethane resin is more preferable. By using the moisture-curable urethane resin, the elongation at break of the cured product is increased, and the adhesive strength is easily increased. In addition, when the high Tg compound B1 or the crosslinking agent (X) described below is used in combination, it becomes easy to further improve the adhesive property.
The moisture-curable urethane resin has an isocyanate group. The moisture-curable urethane resin is cured by reacting an isocyanate group in a molecule thereof with moisture in the air or in an adherend. The moisture-curable urethane resin may have only 1 isocyanate group in 1 molecule, or may have 2 or more. Among them, isocyanate groups are preferably present at both ends of the main chain of the molecule.
The moisture-curable urethane resin can be obtained by reacting "a polyol compound having 2 or more hydroxyl groups in 1 molecule" with "a polyisocyanate compound having 2 or more isocyanate groups in 1 molecule".
The reaction of the above polyol compound with the polyisocyanate compound is usually carried out in a range of [ NCO ]/[ OR ] =2.0 to 2.5 in terms of a molar ratio of hydroxyl groups (OR) in the polyol compound to isocyanate groups (NCO) in the polyisocyanate compound.
As the polyol compound that becomes a raw material of the moisture-curable urethane resin, a known polyol compound that is generally used for producing polyurethane can be used, and examples thereof include: polyester polyols, polyether polyols, polyalkylene polyols, polycarbonate polyols, and the like. These polyol compounds may be used singly or in combination of 1 or more than 2.
Examples of the polyester polyol include: polyester polyols obtained by reacting a polycarboxylic acid with a polyol, poly-epsilon-hexylpropyl ester polyols obtained by ring-opening polymerization of epsilon-hexylpropyl ester, and the like.
Examples of the polycarboxylic acid as a raw material for the polyester polyol include: terephthalic acid, isophthalic acid, 1, 5-naphthalenedicarboxylic acid, 2, 6-naphthalenedicarboxylic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, decamethylenedicarboxylic acid, dodecamethylenedicarboxylic acid, and the like.
Examples of the polyol to be a raw material of the polyester polyol include: ethylene glycol, 1, 2-propylene glycol, 1, 3-propylene glycol, 1, 4-butanediol, neopentyl glycol, 1, 5-pentanediol, 1, 6-hexanediol, diethylene glycol, cyclohexanediol, and the like.
Examples of the polyether polyol include: ethylene glycol, 1, 2-propylene glycol, ring-opening polymers of tetrahydrofuran, ring-opening polymers of 3-methyltetrahydrofuran, random copolymers or block copolymers of these or derivatives thereof, bisphenol-type polyoxyalkylene modifications, and the like.
Here, the bisphenol type polyoxyalkylene modified product is a polyether polyol obtained by addition reaction of an alkylene oxide (a 1ky1 enoxide) (for example, ethylene oxide, propylene oxide, butylene oxide, isobutylene oxide, etc.) with an active hydrogen moiety of a bisphenol type molecular skeleton. The polyether polyol may be a random copolymer or a block copolymer. The bisphenol polyoxyalkylene modified product is preferably obtained by adding 1 or 2 or more kinds of alkylene oxide to both ends of a bisphenol molecular skeleton.
The bisphenol type is not particularly limited, and examples thereof include type a, type F, type S, and the like, and bisphenol a type is preferable.
Examples of the polyalkylene polyol include: polybutadiene polyol, hydrogenated polyisoprene polyol, and the like.
Examples of the polycarbonate polyol include: polyhexamethylene carbonate polyol, polycyclohexane dimethylene carbonate polyol, and the like.
As the polyisocyanate compound that is a raw material of the moisture-curable urethane resin, an aromatic polyisocyanate compound or an aliphatic polyisocyanate compound can be suitably used.
Examples of the aromatic polyisocyanate compound include: diphenylmethane diisocyanate, liquid modified diphenylmethane diisocyanate, polymeric MDI (polymeric MDI), toluene diisocyanate, naphthalene-1, 5-diisocyanate, and the like.
Examples of the aliphatic polyisocyanate compound include: hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate, norbornane diisocyanate, trans-cyclohexane-1, 4-diisocyanate, isophorone diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane diisocyanate, cyclohexane diisocyanate, bis (isocyanatomethyl) cyclohexane, dicyclohexylmethane diisocyanate, and the like.
Among them, diphenylmethane diisocyanate and its modified products are preferable from the viewpoint of improving the adhesive strength after complete curing.
The polyisocyanate compound may be used alone or in combination of 2 or more.
The moisture-curable urethane resin is preferably obtained by using a polyol compound having a structure represented by the following formula (1). By using the polyol compound having the structure represented by the following formula (1), a curable resin composition excellent in adhesion and a cured product having a soft and good elongation and a high elongation at break can be obtained, and the compatibility with the photopolymerizable compound B is excellent. In addition, the storage modulus is easily adjusted to be within the above-described desired range.
Among them, polyether polyols composed of ring-opening polymerization compounds of 1, 2-propanediol, tetrahydrofuran (THF) compounds, or ring-opening polymerization compounds of tetrahydrofuran compounds having a substituent such as methyl group are preferably used. Further, a ring-opening polymerization compound of a tetrahydrofuran compound is more preferable, and polytetramethylene ether glycol is particularly preferable.
In the formula (1), R represents a hydrogen atom, a methyl group or an ethyl group, l is an integer of 0 to 5, m is an integer of 1 to 500, and n is an integer of 1 to 10. l is preferably 0 to 4, m is preferably 50 to 200, and n is preferably 1 to 5. The case where 1 is 0 means that the carbon bonded to R is directly bonded to oxygen.
In the above, the total of n and l is more preferably 1 or more, and still more preferably 3 to 6. R is more preferably a hydrogen atom or a methyl group, and particularly preferably a hydrogen atom.
The hydrolyzable silicon group-containing resin used in the present invention is cured by reacting the hydrolyzable silicon group in the molecule with moisture in the air or in the adherend.
The resin containing a hydrolyzable silicon group may have only 1 hydrolyzable silicon group per 1 molecule, or may have 2 or more hydrolyzable silicon groups. Among them, it is preferable that the molecule has hydrolyzable silicon groups at both ends of the main chain.
The resin containing a hydrolyzable silicon group does not include an isocyanate group.
The hydrolyzable silicon group is represented by the following formula (2).
-SiR 1 3-a X a (2)
In the formula (2), R 1 Each independently is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or an OSiR group which may be substituted 2 3 (R 2 Independently a hydrocarbon group having 1 to 20 carbon atoms). In additionIn formula (2), X is each independently a hydroxyl group or a hydrolyzable group. In formula (2), a is an integer of 1 to 3.
The hydrolyzable group is not particularly limited and examples thereof include: halogen atom, alkoxy group, alkenyloxy group, aryloxy group, acyloxy group, ketoximate (ketoximate) group, amino group, amide group, acid amide group, aminooxy group, mercapto group, and the like. Among them, halogen atom, alkoxy group, alkenyloxy group and acyloxy group are preferable in terms of high activity. In addition, from the viewpoint of stable hydrolyzability and easy handling, an alkoxy group such as a methoxy group or an ethoxy group is more preferable, and a methoxy group or an ethoxy group is further preferable. In addition, from the viewpoint of safety, it is preferable that the compounds that are released by the reaction are ethanol, ethoxy of acetone, and isopropenyloxy (isopropenyloxy), respectively.
The hydroxyl group or the hydrolyzable group may bond 1 silicon atom to 1 to 3 silicon atoms. In the case where the hydroxyl group or the hydrolyzable group is bonded to 1 silicon atom or more than 2, these groups may be the same or different.
From the viewpoint of curability, a in the above formula (2) is preferably 2 or 3, and particularly preferably 3. In addition, from the viewpoint of storage stability, a is preferably 2.
In addition, R in the above formula (2) 1 Examples include: alkyl groups such as methyl and ethyl; cycloalkyl groups such as cyclohexyl; aryl groups such as phenyl; aralkyl groups such as benzyl; trimethylsiloxy, chloromethyl, methoxymethyl, and the like. Among them, methyl is preferable.
Examples of the hydrolyzable silicon group include: methyldimethoxysilyl, trimethoxysilyl, triethoxysilyl, tris (2-propenyloxy) silyl, triacetoxybis silyl, (chloromethyl) dimethoxysilyl, (chloromethyl) diethoxysilyl, (dichloromethyl) dimethoxysilyl, (1-chloroethyl) dimethoxysilyl, (1-chloropropyl) dimethoxysilyl, (methoxymethyl) diethoxysilyl, (ethoxymethyl) dimethoxysilyl, (1-methoxyethyl) dimethoxysilyl, (aminomethyl) dimethoxysilyl, (N, N-dimethylaminomethyl) dimethoxysilyl, (N, N-diethylaminomethyl) diethoxysilyl, (N- (2-aminoethyl) aminomethyl) dimethoxysilyl, (acetoxymethyl) diethoxysilyl, and the like.
Examples of the hydrolyzable silicon group-containing resin include: a (meth) acrylic resin containing a hydrolyzable silicon group, an organic polymer having a hydrolyzable silicon group at a molecular chain end or a molecular chain end position, a polyurethane resin containing a hydrolyzable silicon group, and the like.
The hydrolyzable silicon group-containing (meth) acrylic resin preferably has a repeating structural unit derived from a hydrolyzable silicon group-containing (meth) acrylate and/or an alkyl (meth) acrylate in the main chain.
Examples of the hydrolyzable silicon group-containing (meth) acrylate include: 3- (trimethoxysilyl) propyl (meth) acrylate, 3- (triethoxysilyl) propyl (meth) acrylate, 3- (methyldimethoxysilyl) propyl (meth) acrylate, 2- (trimethoxysilyl) ethyl (meth) acrylate, 2- (triethoxysilyl) ethyl (meth) acrylate, 2- (methyldimethoxysilyl) ethyl (meth) acrylate, trimethoxysilyl methyl (meth) acrylate, triethoxysilyl methyl (meth) acrylate, and (methyldimethoxysilyl) methyl (meth) acrylate.
Examples of the alkyl (meth) acrylate include: methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, cyclohexyl (meth) acrylate, n-heptyl (meth) acrylate, n-octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-nonyl (meth) acrylate, n-decyl (meth) acrylate, n-dodecyl (meth) acrylate, stearyl (meth) acrylate, and the like.
Specifically, examples of the method for producing a hydrolyzable silicon group-containing (meth) acrylic resin include a method for synthesizing a hydrolyzable silicon group-containing (meth) acrylic polymer described in International publication No. 2016/035718.
The organic polymer having a hydrolyzable silicon group at a molecular chain end or a molecular chain end portion has a hydrolyzable silicon group at least one of a terminal of a main chain and a terminal of a side chain.
The skeleton structure of the main chain is not particularly limited, and examples thereof include: saturated hydrocarbon polymers, polyoxyalkylene polymers, (meth) acrylate polymers, and the like.
Examples of the polyoxyalkylene polymer include: and polymers having a polyoxyethylene structure, a polyoxypropylene structure, a polyoxybutylene structure, a polyoxytetramethylene structure, a polyoxyethylene-polyoxypropylene copolymer structure, a polyoxypropylene-polyoxybutylene copolymer structure, and the like.
Specific examples of the method for producing the organic polymer having a hydrolyzable silicon group at a molecular chain end or a molecular chain end region include a method for synthesizing an organic polymer having a crosslinkable silicon group only at a molecular chain end or a molecular chain end region described in International publication No. 2016/035718. Further, as another method for producing the organic polymer having a hydrolyzable silicon group at a molecular chain end or a molecular chain end position, for example, a method for synthesizing a polyoxyalkylene polymer having a reactive silicon group described in international publication No. 2012/117902, and the like are mentioned.
Examples of the method for producing the hydrolyzable silicon group-containing polyurethane resin include: and a method in which a silicon-containing compound such as a silane coupling agent is further reacted when a polyol compound is reacted with a polyisocyanate compound to produce a polyurethane resin. Specifically, examples thereof include: a method for synthesizing a urethane oligomer having a hydrolyzable silicon group as described in Japanese patent application laid-open No. 2017-48345.
Examples of the silane coupling agent include: vinyl trichlorosilane, vinyl triethoxysilane, vinyl tris (beta-methoxyethoxy) silane, beta- (3, 4-epoxycyclohexyl) -ethyl trimethoxysilane, gamma-glycidoxypropyl methyldiethoxysilane, gamma-methacryloxypropyl trimethoxysilane, N- (beta-aminoethyl) -gamma-aminopropyl trimethyldimethoxy silane, N-phenyl-gamma-aminopropyl trimethoxysilane, gamma-chloropropyl trimethoxysilane, gamma-mercaptopropyl trimethoxysilane, gamma-aminopropyl trimethoxysilane, 3-isocyanatopropyl triethoxysilane, and the like. Among them, gamma-mercaptopropyl trimethoxysilane, 3-isocyanatopropyl triethoxysilane are preferable. These silane coupling agents may be used alone or in combination of 2 or more.
In addition, the moisture-curable urethane resin may have both an isocyanate group and a hydrolyzable silicon group. The moisture-curable urethane resin having both an isocyanate group and a hydrolyzable silicon group is preferably produced by: first, a moisture-curable urethane resin having an isocyanate group is obtained by the above method, and then a silicon-on-calcined coupling agent is reacted with the moisture-curable urethane resin.
The moisture-curable urethane resin having an isocyanate group is as described above in detail. The silane coupling agent to be reacted with the moisture-curable urethane resin may be appropriately selected from the above-mentioned examples, but from the viewpoint of reactivity with an isocyanate group, it is preferable to use a silane coupling agent having an amino group or a hydrophobic group. Specific preferable examples include: n- (beta-amino ethyl) -gamma-amino propyl trimethoxy silane, N- (beta-amino ethyl) -gamma-amino propyl trimethyl dimethoxy silane, N-phenyl-gamma-amino propyl trimethoxy silane, 3-hydrophobic propyl trimethoxy silane, gamma-amino propyl trimethoxy silane, 3-isocyanato propyl trimethoxy silane and the like.
Further, the moisture-curable resin (a) may have a radical-polymerizable functional group. The radical polymerizable functional group that the moisture curable resin (a) may have is preferably a group having an unsaturated double bond, and in terms of reactivity, a (meth) acryl group is particularly preferred. The moisture-curable resin having a radical polymerizable functional group is not included in the photopolymerizable compound B described later, and is treated as a moisture-curable resin.
The moisture-curable resin (a) may be used singly or in combination of 1 kind or 2 or more kinds, as appropriate, from the above-mentioned various resins.
The weight average molecular weight of the moisture-curable resin (a) is not particularly limited, but is preferably 800 at a lower limit and 10000 at an upper limit. When the weight average molecular weight is within this range, the storage modulus of the cured product can be easily adjusted within the above range. In addition, when the obtained curable resin composition is cured in its entirety, the crosslinking density does not become too high and the flexibility is excellent, and the fracture strength can be easily adjusted within the above range.
The weight average molecular weight of the moisture-curable resin (a) is more preferably 2000 at a lower limit, 8000 at an upper limit, 2500 at a lower limit, 6000 at an upper limit. In the present specification, the weight average molecular weight is a value obtained by measuring by Gel Permeation Chromatography (GPC) and converting the weight average molecular weight into polystyrene. As a column for measuring the weight average molecular weight in terms of polystyrene by GPC, shodex LF-804 (manufactured by Showa electric Co., ltd.) can be mentioned. The solvent used for GPC includes tetrahydrofuran.
The content of the moisture-curable resin (a) in the curable resin composition is preferably 50 mass% or more based on the total amount of the curable resin composition. When the content of the moisture-curable resin (a) is 50 mass% or more, the elongation at break is increased, and it becomes easy to improve the adhesive properties, particularly the PUSH adhesive force.
From the viewpoint of improving the adhesive property, the content of the moisture-curable resin (a) is preferably 54 mass% or more, and even more preferably 56 mass% or more, based on the total amount of the curable resin composition. The content of the moisture-curable resin (a) is preferably 80 mass% or less, more preferably 70 mass% or less, still more preferably 65 mass% or less, in order to contain the photopolymerizable compound B, the crosslinking agent (X), and the like, which will be described later, in a certain amount.
Further, the total amount of the curable resin composition means: based on the total amount of the solid components contained in the curable resin composition. For example, when the curable resin composition contains a solvent for diluting the composition, the amount of the component after removal of the solvent becomes the total amount of the curable resin composition.
(photopolymerizable Compound B)
The photopolymerizable compound B is not particularly limited as long as it is a radical polymerizable compound having a radical polymerizable functional group in a molecule. The photopolymerizable compound B is preferably a compound having an unsaturated double bond as a radical polymerizable functional group, and particularly preferably a compound having a (meth) acryloyl group (hereinafter, also referred to as a (meth) acrylic compound). In the present invention, the storage modulus and the elongation at break can be easily adjusted to a specific range by using the (meth) acrylic compound.
Examples of the (meth) acrylic compound include: (meth) acrylate compounds, epoxy (meth) acrylates, (meth) acrylic urethanes, and the like. Among these, (meth) acrylate compounds are preferable. Furthermore, the urethane (meth) acrylate has no residual isocyanate groups.
In addition, in the present specification, (meth) acryl means acryl or methacryl, and (meth) acrylate means acrylate or methacrylate, and other similar terms are also the same.
The (meth) acrylate compound may be monofunctional, may be 2-functional, or may be 3-functional or more, but is preferably monofunctional.
Examples of the monofunctional (meth) acrylate compound include: alkyl (meth) acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isononyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, tetradecyl (meth) acrylate, isotetradecyl (meth) acrylate, hexadecyl (meth) acrylate, stearyl (meth) acrylate, and isostearyl (meth) acrylate; alicyclic (meth) acrylates such as cyclohexyl (meth) acrylate, 4-t-butylcyclohexyl (meth) acrylate, 3, 5-trimethylcyclohexyl (meth) acrylate, isobornyl (meth) acrylate, tricyclo [5.2.1.02,6] dec-8-yl (meth) acrylate, dicyclopentenyl (meth) acrylate, and 1-adamantyl (meth) acrylate; hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate; alkoxyalkyl (meth) acrylates such as 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, and 2-butoxyethyl (meth) acrylate; alkoxy glycol (meth) acrylates such as methoxy glycol (meth) acrylate and ethoxy glycol (meth) acrylate; polyoxyethylene (meth) acrylates such as methoxy diethylene glycol (meth) acrylate, methoxy triethylene glycol (meth) acrylate, methoxy polyethylene glycol (meth) acrylate, ethyl carbitol (meth) acrylate, ethoxy diethylene glycol (meth) acrylate, ethoxy triethylene glycol (meth) acrylate, and ethoxy polyethylene glycol (meth) acrylate.
Further, the (meth) acrylate compound may have an aromatic ring, and examples thereof include: phenyl alkyl (meth) acrylates such as benzyl (meth) acrylate and 2-phenylethyl (meth) acrylate; phenoxyethyl (meth) acrylate and other phenoxyalkyl (meth) acrylate. Further, (meth) acrylic esters having a plurality of benzene rings such as fluorene skeleton and biphenyl skeleton may be used, and specific examples thereof include: fluorene (meth) acrylate, ethoxylated ortho-phenylphenyl acrylate, and the like.
Further, it is also possible to list: phenoxy polyoxyethylene (meth) acrylates such as phenoxy diethylene glycol (meth) acrylate, phenoxy polyethylene glycol (meth) acrylate, nonylphenoxy diethylene glycol (meth) acrylate, nonylphenoxy polyethylene glycol (meth) acrylate, and the like.
Further, as the monofunctional (meth) acrylate compound, there may be mentioned: (meth) acrylic acid esters having a heterocyclic structure such as tetrahydrofurfuryl (meth) acrylate, cyclic trimethylolpropane formal (meth) acrylate, and (3-ethyl-3-oxetanyl) methyl (meth) acrylate; phthalimide acrylates such as N-acryloyloxyethyl hexahydrophthalimide; various imide (meth) acrylates, 2-trifluoroethyl (meth) acrylate, 2, 3-tetrafluoropropyl (meth) acrylate, lH, 5H-octafluoropentane (meth) acrylate, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, 2- (meth) acryloyloxyethyl succinic acid, 2- (meth) acryloyloxyethyl hexahydrophthalic acid, 2- (meth) acryloyloxyethyl-2-hydroxypropyl phthalate, epoxypropyl (meth) propanoate, 2- (meth) acryloyloxyethyl phosphate, and the like.
Examples of the 2-functional group in the (meth) acrylate compound include: 1, 3-butanediol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, 1, 9-nonanediol di (meth) acrylate, 1, 10-decanediol di (meth) acrylate, 2-n-butyl 2-ethyl-1, 3-propanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate ethylene oxide addition bisphenol A di (meth) acrylate, propylene oxide addition bisphenol A di (meth) acrylate, ethylene oxide addition bisphenol F di (meth) acrylate, dimethylol dicyclopentadiene di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene oxide modified isocyanuric acid di (meth) acrylate, (meth) acrylic acid (2-hydroxy-3- (meth) acryloyloxy) propyl ester, carbonate diol di (meth) acrylate, polyether diol di (meth) acrylate, polyester diol di (meth) acrylate, polycaprolactone diol di (meth) acrylate, polybutadiene diol di (meth) acrylate, and the like.
Examples of the 3-functional group or more in the (meth) acrylate compound include: trimethylolpropane tri (meth) acrylate, ethylene oxide-added trimethylolpropane tri (meth) acrylate, propylene oxide-added trimethylolpropane tri (meth) acrylate, hexylpropyl ester-modified trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, ethylene oxide-added isocyanuric acid tri (meth) acrylate, glycerol tri (meth) acrylate, propylene oxide-added glycerol tri (meth) acrylate, tris (meth) acryloxyethyl phosphate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like.
Examples of the epoxy (meth) acrylate include those obtained by reacting an epoxy compound with (meth) acrylic acid. The reaction of the epoxy compound with (meth) acrylic acid may be carried out in the presence of a basic catalyst or the like according to a conventional method. The epoxy (meth) acrylate may be monofunctional or may be multifunctional such as 2-functional.
Examples of the epoxy compound that is a raw material for synthesizing the epoxy (meth) acrylate include: bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, 2' -diallyl bisphenol A type epoxy resin, hydrogenated bisphenol type epoxy resin, propylene oxide addition bisphenol A type epoxy resin, resorcinol type epoxy resin, biphenyl type epoxy resin, sulfide type epoxy resin, diphenyl ether type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, phenol novolak type epoxy resin, o-cresol novolak type epoxy resin, dicyclopentadiene novolak type epoxy resin, biphenyl novolak type epoxy resin, naphthol novolak type epoxy resin, glycidol type epoxy resin, alkyl polyol type epoxy resin, rubber modified type epoxy resin, epoxypropyl ester compound, bisphenol A type annular sulfur (episulf) resin, and the like.
Examples of the epoxy (meth) acrylate which are commercially available include: EBECRYL860, EBECRYL3200, EBECRYL3201, EBECRYL3412, EBECRYL3600, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRYL3703, EBECRYL3800, EBECRYL6040, and EBECRYL lrdx63182 (all manufactured by elk encaustic corporation); EA-1010, EA-1020, EA-5323, EA-5520, EACHD, EMA-1020 (all manufactured by Xinzhongcun chemical industry Co., ltd.); the patent refers to the field of 'electric power transmission'. The term "hu" as used herein refers to the term "hu" as used herein, and includes but is not limited to "hu" as used herein, but is not limited to "du" as used herein, du コ, du-141, du コ, du-314, du- コ, and so on.
The urethane (meth) acrylate may be obtained by, for example, "reacting a (meth) acrylic acid derivative having a hydroxyl group with an isocyanate compound". The reaction of the isocyanate compound with the (meth) propane acid derivative may be carried out using a catalytic amount of a tin compound or the like as a catalyst. The urethane (meth) acrylate may be monofunctional or may be multifunctional such as 2-functional.
Examples of the isocyanate compound used for obtaining urethane (meth) acrylate include: polyisocyanate compounds such as isophorone diisocyanate, 2, 4-toluene diisocyanate, 2, 6-toluene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4, 4' -diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1, 5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, xylylene Diisocyanate (XDI), hydrogenated XD1, lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanatophenyl) thiophosphate, tetramethylxylylene diisocyanate, and 1,6, 11-undecane triisocyanate.
Further, as the isocyanate compound, a chain-extended polyisocyanate compound obtained by reacting a polyol with an excessive amount of the isocyanate compound can also be used. Examples of the polyol include: ethylene glycol, 1, 2-propanediol, glycerol, sorbitol, trimethylolpropane, carbonate glycol, polyether glycol, polyester glycol, polycaprolactone glycol, and the like.
Examples of the (meth) acrylic acid derivative having a hydroxyl group include: mono (meth) acrylic acid esters of dihydric alcohols such as ethylene glycol, 1, 2-propylene glycol, 1, 3-butanediol, 1, 4-butanediol, and polyethylene glycol; or mono (meth) acrylic acid esters or di (meth) acrylic acid esters of triols such as trimethylolethane, trimethylolpropane, glycerol, etc.; or epoxy (meth) acrylates such as bisphenol a epoxy (meth) acrylate.
Examples of the commercial products of the urethane (meth) acrylate include: m-1100, M-1200, M-1210, M-1600 (all manufactured by east Asia Synthesis Co.); EBECRYL230, EBECRYL270, EBECRYL8402, EBECRYL84ll, EBECRYL8412, EBECRYL84l3, EBECRYL8804, EBECRYL8803, EBECRYL8807, EBECRYL9270, EBECRYL2l0, EBECRYL4827, EBECRYL6700, EBECRYL220, EBECRYL2220 (all manufactured by Takara Shuzo Co., ltd.); one end of the cord is not limited to UN-9000H, one end of the cord is not limited to 9000A, one end of the cord is not limited to UN-7100 one end of the cord is not limited to UN-1255, one end of the cord is not limited to UN-330, and the other end of the cord is not limited to UN-330 one end of the cord is 3320HB, one end of the cord is UN-1200TPK one-step SH-500B (all manufactured by root industries); u-2HA, U-2PHA, U-3HA, U-4HA, U-6H, U-6LPA, U-6HA, U-l0H, U-15HA, U-122A, U-122P, U-l08, U-l08A, U-324A, U-340A, U-340P, U-l084A, U-206lBA, UA-340P, UA-4l00, UA-4000, UA-4200, UA-4400, UA-520lP, UA7100, UA-7200, UA-W2A (all manufactured by Xinzhongcun chemical Co., ltd.), al-600, AH600, AT600, UA-101I, UA101T, UA-306H, UA-306I, UA-306T (all manufactured by Zoo chemical Co., ltd.). CN-902, CN-973, CN-902l, CN-9782, CN-9833 (all manufactured by ALKOMALYM), and the like.
The (meth) acrylic compound may be used alone in an amount of 1 or 2 or more.
The photopolymerizable compound B is preferably a monofunctional (meth) acrylic compound or a vinyl compound other than the (meth) acrylic compound. As such a compound, a (meth) acrylic compound having a cyclic structure such as (meth) acryloylmorpholine, or a vinyl compound having a cyclic structure such as N-vinyl-2-pyrrolidone or N-vinyl-epsilon-caprolactam can be used. Further, for example, a (meth) acrylamide compound such as N, N-dimethyl (meth) acrylamide, N-hydroxyethyl (meth) acrylamide, N-diethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N-dimethylaminopropyl (meth) acrylamide, or the like can be used.
In the present invention, the storage modulus and elongation at break of the cured product can be adjusted by appropriately selecting the photopolymerizable compound B. For example, the photopolymerizable compound B preferably contains a compound B1 (high Tg compound B1) having a glass transition temperature (Tg) of 70 ℃ or higher after formation of a homopolymer. When such a high Tg compound B1 is used, the storage modulus tends to be improved.
The glass transition temperature (Tg) may be measured by synthesizing a homopolymer of each compound. Specifically, it means: the temperature at which the maximum value of the loss tangent (tan δ) caused by the micro-Brownian motion is expressed as the maximum value of the loss tangent (tan δ) obtained by measuring the dynamic viscoelasticity of the synthesized homopolymer can be measured by a conventionally known method using a dynamic viscoelasticity measuring apparatus. The homopolymer can be synthesized, for example, by flowing the monomer components constituting the homopolymer into a Teflon (registered trademark) mold having a width of 3mm, a length of 30mm and a thickness of 1mm, and irradiating 1000mJ/cm with UV-LED (wavelength of 365 nm) 2 And photo-curing the resultant material with ultraviolet rays to obtain a cured product sample. The dynamic viscoelasticity can be measured by using the obtained cured product sample and measuring the dynamic viscoelasticity at a temperature in the range of-50 to 160℃using a dynamic viscoelasticity measuring device.The measurement conditions were that the strain was set to 1% by stretching in the deformation mode, the measurement frequency was 1Hz, and the temperature rise rate was 5 ℃/min. In addition, polymer Handbook (3 rd edition, john Wiley may also be used&Sons et al, inc, 1989) and the like.
The content of the compound B1 is preferably: the content of the photopolymerizable compound B is 10 to 50 mass% based on the total amount of the photopolymerizable compound B. When the content of the compound B1 is within the above range, the storage modulus and the elongation at break are easily improved, and the adhesive property and the impact resistance are easily improved. From these viewpoints, the content of the compound B1 is more preferably: the content of the photopolymerizable compound B is 10 mass% or more and 40 mass% or less, and still more preferably 14 mass% or more and 35 mass% or less, based on the total amount of the photopolymerizable compound B.
Further, from the same viewpoint, the content of the compound B1 is preferably: the amount of the curable resin composition is 2.5% by mass or more and 15% by mass or less, more preferably 3.2% by mass or more and 13% by mass or less, still more preferably 5.0% by mass or more and 11% by mass or less, based on the total amount of the curable resin composition.
The photopolymerizable compound B preferably contains, in addition to the above compound B1, a compound B2 (low Tg compound B2) having a glass transition temperature (Tg) of less than 70 ℃ after formation of a homopolymer. By containing the low Tg compound B2 in addition to the high Tg compound B1, the storage modulus and the elongation at break can be improved in a well-balanced manner, and the adhesive property and the impact resistance can be easily improved. From such a viewpoint, the content of the low Tg compound B2 may be 50% by mass or more based on the total amount of the photopolymerizable compound B, but is preferably 50% by mass or more and 90% by mass or less, more preferably 60% by mass or more and 90% by mass or less, and still more preferably 65% by mass or more and 86% by mass or less.
From the same point of view, the content of the low Tg compound B2 is preferably: the amount of the curable resin composition is 12% by mass or more and 35% by mass or less, more preferably 16% by mass or more and 29% by mass, still more preferably 20% by mass or more and 27% by mass or less, based on the total amount of the curable resin composition.
From the viewpoint of improving the adhesion and impact resistance with good balance, as the high Tg compound B1, "the glass transition temperature after formation of a homopolymer is preferably 200 ℃ or less, more preferably 160 ℃ or less, and preferably 80 ℃ or more, more preferably 90 ℃ or more".
On the other hand, as the low Tg compound B2, "the glass transition temperature after formation of a homopolymer is preferably 60 ℃ or lower, more preferably 45 ℃ or lower, and preferably-20 ℃ or higher, more preferably-10 ℃ or higher".
The photopolymerizable compound B preferably contains a (meth) acrylic compound having an alicyclic structure. Here, the alicyclic structure may form a ring with only carbon atoms, or may contain hetero atoms such as nitrogen, oxygen, sulfur, and the like. As the hetero atom, a nitrogen atom is preferable. The alicyclic structure-containing (meth) acrylic compound is preferably monofunctional. By making it monofunctional, the elongation at break is easily improved. By containing the alicyclic structure-containing (meth) acrylic compound in the photopolymerizable compound B, the elongation at break of the cured product can be easily increased. Further, by containing the alicyclic structure-containing (meth) acrylic compound in the photopolymerizable compound B, when the moisture-curable resin (a) is a moisture-curable urethane resin, compatibility with the moisture-curable resin (a) is improved, and various performances can be easily improved.
The alicyclic structure-containing (meth) acrylic compound is preferably a high Tg compound B1 (i.e., tg after formation of a homopolymer is 70 ℃ or higher). When the alicyclic structure-containing (meth) acrylic compound is used as the high Tg compound B1, both the storage modulus and the elongation at break of the cured product are easily improved.
As the alicyclic structure-containing (meth) acrylic compound which can be used as the high Tg compound B1, there can be mentioned: and alicyclic (meth) acrylates such as tricyclo [5.2.1.02,6] dec-8-yl methacrylate (Tg: 175 ℃), tricyclo [5.2.1.02,6] dec-8-yl acrylate (Tg: 120 ℃), isobornyl methacrylate (Tg: 173 ℃), isobornyl acrylate (Tg: 94 ℃), 1-adamantyl methacrylate (Tg: 250 ℃), 1-adamantyl acrylate (Tg: 153 ℃), 4-t-butylcyclohexyl acrylate (Tg: 80 ℃), or alicyclic (meth) acrylic compounds having hetero atoms in the alicyclic structure such as acryloylmorpholine (Tg: 145 ℃), and the like. Among these, isobornyl acrylate, acryloylmorpholine and 4-t-butylcyclohexyl acrylate are preferable, and isobornyl acrylate and acryloylmorpholine are more preferable. These alicyclic structure-containing (meth) acrylic compounds may be used alone in an amount of 1 or 2 or more.
The content of the alicyclic structure-containing (meth) acrylic compound which is the high Tg compound B1 is preferably 5% by mass or more and 50% by mass or less, more preferably 10% by mass or more and 40% by mass or less, still more preferably 14% by mass or more and 35% by mass or less, based on the total amount of the photopolymerizable compound B.
The high Tg compound B1 is not necessarily a (meth) acrylic compound having an alicyclic structure, and a photopolymerizable compound other than the (meth) acrylic compound having an alicyclic structure may be used. As such a compound, there may be mentioned: methyl methacrylate (Tg: 105 ℃ C.), alkyl (meth) acrylates such as t-butyl methacrylate (Tg: 118 ℃ C.), dimethylacrylamide (Tg: 119 ℃ C.), diethylacrylamide (Tg: 81 ℃ C.), dimethylaminopropylacrylamide (Tg: 134 ℃ C.), isopropylacrylamide (Tg: 134 ℃ C.), hydroxyethylacrylamide (Tg: 98 ℃ C.), and other vinyl monomers containing amide groups. These may be used in combination with the alicyclic structure-containing (meth) acrylic compound as the high Tg compound B1, or may be used alone as the high Tg compound B1.
The low Tg compound B2 is not particularly limited, and from the viewpoint of reactivity and the like, an alkyl (meth) acrylate is preferably used. As the alkyl (meth) acrylate, an alkyl (meth) acrylate having an alkyl group with a carbon number of 1 to 18 is used, and an alkyl (meth) acrylate having an alkyl group with a carbon number of 12 to 18 is preferably used. The alkyl group may be linear or branched. The alkyl (meth) acrylate as the low Tg compound B2 may be used alone in an amount of 1 or 2 or more. Preferable examples of such alkyl (meth) acrylate include lauryl acrylate (tg= -3 ℃) and stearyl acrylate (tg=35℃).
The content of the alkyl (meth) acrylate which is the low Tg compound B2 is, for example, 40% by mass or more, preferably 45% by mass or more and 90% by mass or less, more preferably 50% by mass or more and 89% by mass or less, still more preferably 60% by mass or more and 86% by mass or less, based on the total amount of the photopolymerizable compound B.
The content of the photopolymerizable compound B in the curable resin composition is preferably 15 mass% or more, more preferably 20 mass% or more, still more preferably 25 mass% or more, based on the total amount of the curable resin composition. The content of the photopolymerizable compound B is preferably 45 mass% or less, more preferably 40 mass% or less, still more preferably 35 mass% or less, and still more preferably 31.5 mass% or less, based on the total amount of the curable resin composition. When the content of the photopolymerizable compound B is within the above range, the elongation at break and the storage modulus can be within specific ranges, and thus the adhesive properties, impact resistance and the like can be easily improved. Further, if the amount of the photopolymerizable compound B is made small, for example, the storage modulus and elongation at break of the cured product can be easily improved even if the compound B1 is not used.
The ratio (B/a) of the content of the photopolymerizable compound B to the moisture-curable resin (a) in the curable resin composition is preferably 0.30 to 0.80, more preferably 0.35 to 0.65, still more preferably 0.40 to 0.55, based on the total amount of the curable resin composition. When the content ratio (B/a) is within the above range, the elongation at break and the storage modulus can be within the specific ranges, and the adhesive properties, impact resistance and the like can be easily improved. Further, when the content is 0.55 or less, the storage modulus and elongation at break of the cured product can be improved even if the compound B1 is not used.
(crosslinking agent (X))
The curable resin composition of the present invention preferably contains a crosslinking agent (X). By containing the crosslinking agent (X), the elongation at break and storage modulus can be improved, and the adhesive property and impact resistance can be easily improved. The crosslinking agent (X) is preferably a compound having a functional group capable of reacting with at least one of the moisture-curable resin (a) and the photopolymerizable compound B when the curable resin composition is cured. Specifically, a compound having an isocyanate group is exemplified. Examples of such a compound include polyisocyanate compounds having 2 or more isocyanate groups in 1 molecule.
Examples of the polyisocyanate compound used as the crosslinking agent (X) include aromatic polyisocyanate compounds and aliphatic polyisocyanate compounds. Examples of the aromatic polyisocyanate compound include: diphenylmethane diisocyanate, liquid modified diphenylmethane diisocyanate, polymeric MDI, toluene diisocyanate, naphthalene-1, 5-diisocyanate, and the like.
Examples of the aliphatic polyisocyanate compound include: hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate, norbornane diisocyanate, trans-cyclohexane 1, 4-diisocyanate, isophorone diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane diisocyanate, cyclohexane diisocyanate, bis (isocyanatomethyl) cyclohexane, dicyclohexylmethane diisocyanate, and the like.
The polyisocyanate compound is preferably an aromatic polyisocyanate compound, more preferably diphenylmethane diisocyanate and its modified products, and polymeric MDI, and even more preferably diphenylmethane diisocyanate, from the viewpoint of improving storage modulus and improving adhesion performance.
The polyisocyanate compound may be used alone or in combination of 2 or more.
The content of the crosslinking agent (X) in the curable resin composition is preferably 0.4 mass% or more and 10 mass% or less based on the total amount of the curable resin composition. When the content of the crosslinking agent (X) is 0.4 mass% or more, the storage modulus and elongation at break can be easily controlled to a specific value or more, and the adhesive strength and the like can be easily improved. In addition, when the content of the crosslinking agent is 0.4 mass% or more, for example, the storage modulus and elongation at break are easily set to a specific value or more even if the high Tg compound B1 is not used. On the other hand, when the content is 10 mass% or less, the content of the moisture-curable resin (a) and the photopolymerizable compound B can be ensured in a certain amount or more, and therefore, the elongation at break and the like can be easily improved, and the adhesive strength and impact resistance can be improved.
The content of the crosslinking agent is more preferably 0.8 mass% or more, still more preferably 1.0 mass% or more, from the viewpoint of easiness in improving storage modulus and the like. The content of the crosslinking agent is more preferably 6 mass% or less, still more preferably 5 mass% or less, and still more preferably 3 mass% or less, from the viewpoint of easily maintaining the elongation at break at a high value.
(photopolymerization initiator (Y))
When the photopolymerizable compound B is used, the curable resin composition of the present invention preferably contains a photopolymerization initiator (Y) in order to ensure photocurability.
The photopolymerization initiator (Y) may be a photo radical polymerization initiator. Specifically, examples thereof include diphenyl ketone compounds; benzophenone compounds such as α -aminoalkylbenzophenone and α -hydroxyalkylbenzophenone; an acyl phosphine oxide compound; a titanocene compound; oxime ester compounds; benzoin ether compounds; 9-thioxanthone, and the like. Among these, a benzophenone compound is preferable, and an α -aminoalkylbenzophenone is more preferable, from the viewpoint of easy adjustment of elongation at break and storage modulus within specific ranges.
Examples of commercial products of the photopolymerization initiator include: IRGACURE184, IRGACURE369, IRGACURE379EG, IRGACURE651, IRGACURE784, IRGACURE819, IRGACURE907, IRGACURE2959, IRGACURE EOXE01, and larken TPO (all manufactured by BASF corporation); benzoin methyl ester, benzoin ethyl ether, benzoin isopropyl ether (all manufactured by tokyo chemical industry company), and the like.
The content of the photopolymerization initiator (Y) in the curable resin composition is preferably 0.01 parts by mass or more and 10 parts by mass or less, more preferably 0.5 parts by mass or more and 5 parts by mass or less, relative to 100 parts by mass of the photopolymerizable compound. When the content of the photopolymerization initiator (Y) is within this range, the obtained curable resin composition is excellent in photocurability and storage stability. Further, when the content is within the above range, the photopolymerizable compound B is appropriately cured, and the storage modulus and the elongation at break can be easily adjusted within the specific ranges.
(filler)
The curable resin composition of the present invention may contain a filler. By containing the filler, the curable resin composition of the present invention can have an appropriate shake-out property, and can sufficiently maintain the shape after coating. As the filler, a particulate filler may be used.
The filler is preferably an inorganic filler, and examples thereof include silica, talc, titanium oxide, zinc oxide, and calcium carbonate. Among these, silica is preferable in terms of excellent ultraviolet ray transmittance of the obtained curable resin composition. The filler may be subjected to a hydrophobic surface treatment such as a silylation treatment, an alkylation treatment, or an epoxidation treatment.
The filler may be used alone or in combination of 1 or more than 2.
The content of the filler is preferably 1% by mass or more and 20% by mass or less, more preferably 2% by mass or more and 15% by mass or less, and still more preferably 5% by mass or more and 12% by mass or less, based on the total amount of the curable resin composition.
(coupling agent)
The curable resin composition may also contain a coupling agent. By containing the coupling agent, the adhesion is easily improved. Examples of the coupling agent include: silane coupling agents, titanate coupling agents, zirconate coupling agents, and the like. Among them, a silane coupling agent is preferable in terms of excellent effect of improving adhesion. The above coupling agents may be used alone or in combination of 2 or more.
The content of the coupling agent is preferably 0.05 mass% or more and 5 mass% or less, more preferably 0.2 mass% or more and 2 mass% or less, and still more preferably 0.5 mass% or more and 1.5 mass% or less, based on the total amount of the curable resin composition. By setting the content of the coupling agent within these ranges, the storage modulus and the like are not affected, and the adhesion is improved.
The curable resin composition of the present invention may be diluted with a solvent as needed. When the curable resin composition is diluted with a solvent, the mass parts of the curable resin composition are based on the solid content, that is, the mass parts excluding the solvent.
The curable resin composition may contain, in addition to the above-described components, additives such as wax particles, metal-containing particles, opacifying agents, colorants, reactive diluents, and moisture curing acceleration catalysts.
As a method for producing the curable resin composition, a mixer may be used to mix the components constituting the curable resin composition. For example, the following methods are listed: a method in which the moisture-curable resin (A), the photopolymerizable compound B, and optionally, the crosslinking agent (X), the photopolymerization initiator (Y), the filler, the coupling agent, and other additives are mixed. Examples of the mixer include: homogeneous dispersion machines, homogeneous mixers, universal mixers, planetary mixers (planetary stirring devices), kneaders, three-roll mills, and the like.
[ method of Using curable resin composition ]
The curable resin composition of the present invention can be cured and used as a cured product. When the curable resin composition of the present invention has photocurability, thermosetting property, or both of these curability, it is sufficient to first perform photocurability, thermosetting property, or both of these curability by light irradiation or heating to obtain a B-stage state (semi-cured state), and then further perform curing by moisture to completely cure the resin composition. The curable resin composition of the present invention is preferably photo-moisture curable. Therefore, the light irradiation is performed to cure the resin composition to a B-stage state (semi-cured state), and then the moisture is further used to cure the resin composition to complete the curing.
Here, when the curable resin composition is disposed between the adherends and the adherends are joined, it is sufficient to apply the curable resin composition to one adherend, then, to cure the adherend by light irradiation, for example, to form a B-stage state, and to superimpose the other adherend on the "curable resin composition cured to the B-stage state" and to temporarily adhere the adherends with a proper adhesive force (initial adhesive force). Thereafter, the curable resin composition in the B-stage state is cured by moisture to be cured completely, whereby the bonded body-to-body joint that is overlapped with the curable resin composition interposed therebetween is bonded with a sufficient adhesive force.
Here, the light to be irradiated during the photo-curing is not particularly limited as long as it is light to cure the photopolymerizable compound B, and is preferably ultraviolet light. In the heat curing, the temperature at which the heat-curable resin is cured is not particularly limited, and the resin may be heated to a temperature of 60 ℃ or higher and lower than 120 ℃, more preferably lower than 100 ℃. In curing the curable resin composition with moisture, the composition may be left in the atmosphere for a predetermined period of time.
The curable resin composition of the present invention is preferably used as an adhesive for electronic devices. The curable resin composition of the present invention is more preferably used as an adhesive for portable electronic devices. More specifically, the mobile electronic device includes a mobile phone such as a smart phone, a tablet terminal, and the like. When these portable electronic devices are dropped by mistake during use, there are cases where parts are detached, but when the curable resin composition of the present invention is used as an adhesive for portable electronic devices, the cured product of the curable resin composition of the present invention has excellent PUSH adhesion and impact resistance, and therefore parts are difficult to detach.
In the electronic device, the adherend is not particularly limited, and is, for example, various components constituting the electronic device. As various components constituting the electronic device, electronic components, substrates on which electronic components are mounted, and the like are exemplified by: various electronic components provided in the display module, substrates on which the electronic components are mounted, semiconductor chips, and the like. That is, in the present invention, an electronic component including a cured product of the curable resin composition is also provided.
The material of the adherend may be any of metal, glass, plastic, and the like. The shape of the adherend is not particularly limited, and examples thereof include: film-like, sheet-like, plate-like, panel-like, disk-like, rod (stick) like, box-like, shell-like, etc.
The curable resin composition of the present invention has a cured product of the curable resin composition having a specific storage modulus and elongation at break, and therefore exhibits high adhesion, particularly PUSH adhesion, and excellent impact resistance. Therefore, even when the application width or the bonding area of the curable resin composition is small, for example, when a strong impact is applied to the adherend, the curable resin composition of the present invention can prevent the occurrence of peeling of the adherend due to the impact being transmitted to the electronic component.
Therefore, the adhesive can be suitably used as an adhesive for bonding semiconductor chips having a small bonding area to each other or an adhesive used in a display device such as a display device for a portable electronic device (particularly a display device for a portable telephone such as a smart phone) having a coating width which is easily small.
Examples (example)
The present invention will be further described in detail with reference to examples, but the present invention is not limited to these examples.
In this example, measurement of various physical properties and evaluation of performance were performed as follows.
(storage modulus)
A cured product sample was prepared from the curable resin composition according to the method described in the specification, and the storage modulus at 25℃of the cured product sample was measured by a dynamic viscoelasticity measuring apparatus (manufactured by IT Meter. And Control, inc. under the trade name DVA-200).
(elongation at break)
Test pieces were prepared from the curable resin compositions according to the methods described in the specification, and the test pieces were stretched at a speed of 50 mm/min until they were broken by using a tensile tester (trade name TENSILON, manufactured by a & D Company), and the elongation at break at 25 ℃.
(PUSH adhesion test)
An outline of the PUSH adhesion test is shown in fig. 1. As shown in FIG. 1 (a), a part having 3 at the center is preparedA polycarbonate plate 3 with a thickness of 2mm for a rectangular hole 2 of 8mm by 50 mm. The curable resin composition 1 was applied to the polycarbonate plate 3 in a square frame shape so as to have an outer diameter of 46mm×61mm, an inner diameter of 44mm×59mm, and an application width of 1mm and to surround the rectangular hole 2. By irradiating ultraviolet rays 1000mJ/cm using UV-LED (wavelength 365 nm) 2 And the curable resin composition 1 is photo-cured. Then, a glass plate 4 having a thickness of 4mm and a thickness of 50mm×75mm was attached to the polycarbonate plate 3 via the semi-cured curable resin composition 1, and the test body was assembled. The glass plate 4 and the square frame-shaped curable resin composition 1 are disposed so that the center position coincides.
Then, the glass plate 3 was placed on the glass plate 4 by turning over the glass plate from the state shown in fig. 1 (a), and the glass plate 4 and the polycarbonate plate 3 were bonded via the fully cured curable resin composition 1 by moisture curing the curable resin composition 1 at room temperature (23 ℃) for 24 hours under a pressure of 5kgf applied from the polycarbonate plate 3 side.
Next, as shown in fig. 1 (b), the test body was fixed to the support 5 so that the glass plate 4 was positioned at the lower side, and a load was applied to the glass plate 4 at a speed of 10mm/min through the rectangular hole 2, and the load value at the time of peeling the glass plate 4 was measured.
(impact resistance test)
An outline of the impact resistance test is shown in fig. 2. First, a test body was produced in the same manner as in the PUSH adhesion test. Next, as shown in fig. 2 (b), the fabricated test piece was fixed to the support 5, and dropped from a height of 20mm so that "the iron balls 6 having a size of the rectangular hole 2 and a weight of 200g could pass through the rectangular hole 2". The dropping of the iron ball was repeated under the same conditions, and the impact resistance was determined based on the following evaluation criteria.
A: the glass plate is peeled off after the iron ball falls more than 40 times.
B: the glass plate is peeled off after the iron ball falls down less than 40 times.
(moisture-curable resin (A))
The moisture-curable urethane resin a was prepared according to the following synthesis example 1.
Synthesis example 1
100 parts by mass of polytetramethylene ether glycol (product name: PTMG-2000, manufactured by Mitsubishi chemical corporation) and 0.01 part by mass of dibutyltin dilaurate as a polyol compound were charged into a 500-mL separable flask, and stirred at 100℃for 30 minutes under vacuum (20 mmHg or less) to mix. Thereafter, 26.5 parts by mass of diphenylmethane diisocyanate (product name Pure MDI manufactured by soh corporation) as a polyisocyanate compound was added thereto at normal pressure, and the mixture was stirred at 80 ℃ for 3 hours to react the resultant mixture, thereby obtaining a moisture-curable urethane resin a (weight average molecular weight: 2700).
The moisture-curable urethane resin B was prepared according to the following synthesis example 2.
Synthesis example 2
9.8 parts by mass of 3-mercaptopropyl-trimethoxysilane (KBM-803, manufactured by Xinyue chemical industries Co., ltd.) was added to a reaction vessel containing 100 parts by mass of the moisture curable urethane resin A obtained in the same manner as in Synthesis example 1. Then, the mixture was stirred at 80℃for 1 hour, and the mixture was mixed to form a silicone-containing urethane resin, whereby a moisture-curable urethane resin B (weight average molecular weight 3100) having an isonitryl group and a trimethoxysilyl group at the molecular terminal was obtained.
The components other than the moisture-curable urethane resins used in the examples and comparative examples are as follows.
(photopolymerizable Compound B)
Isobornyl acrylate: commercial Co-available chemical Co-Ltd., trade name IB-XA, monofunctional, tg:94 DEG C
Acryloylmorpholine: KJ chemical manufacturing, trade name ACMO, monofunctional, tg: lauryl acrylate at 145 ℃): the trade name of the brand L-A manufactured by Kagaku chemical Co., ltd., monofunctional and Tg: -3 DEG C
Stearyl acrylate: the trade name SR257, monofunctional, tg:35 DEG C
(crosslinking agent (X))
Diphenylmethane diisocyanate
(photopolymerization initiator (Y))
Bis (2, 4, 6-trimethylbenzoyl) -phenylphosphine oxide: manufactured by BASF corporation under the trade name IRGACURE 819
(filler)
Silicon oxidation treatment of silicon dioxide: RY300, trade name, manufactured by Japanese industrial company
(coupling agent)
3-acryloxypropyl trimethoxysilane: KBM-5103, trade name, manufactured by Xinyue chemical industry Co Ltd
Examples 1 to 8 and comparative examples 1 to 5
According to the formulation shown in Table 1, the materials were stirred at a temperature of 50℃by a planetary stirring apparatus (Ivora, miro) and then uniformly mixed at a temperature of 50℃by a ceramic three-roll mill to obtain curable resin compositions of examples 1 to 8 and comparative examples 1 to 5.
TABLE 1
As shown in the examples above, both the storage modulus at 25 ℃ and the elongation at break of the cured product were improved, and the resulting cured product was excellent in both PUSH adhesion and impact resistance. On the other hand, as shown in comparative examples, if one of the storage modulus and the elongation at break is lower than the predetermined value, both the PUSH adhesion and the impact resistance cannot be excellent.
Symbol description
1: curable resin composition
2: rectangular hole
3: polycarbonate plate
4: glass plate
5: supporting table
6: iron ball
Claims (12)
1. A curable resin composition comprising a moisture-curable resin (A),
the cured product of the curable resin composition has a storage modulus of 10MPa or more at 25 ℃ and an elongation at break of 700% or more at 25 ℃,
further comprises a photopolymerizable compound (B) and a photopolymerization initiator (Y),
the photopolymerizable compound (B) contains a compound B1 having a glass transition temperature (Tg) of 70 ℃ or higher after formation of a homopolymer.
2. A curable resin composition comprising a moisture-curable resin (A),
the cured product of the curable resin composition has a storage modulus of 10MPa or more at 25 ℃ and an elongation at break of 700% or more at 25 ℃,
Further comprises a photopolymerizable compound (B) and a photopolymerization initiator (Y),
the photopolymerizable compound (B) includes a (meth) acrylic compound having an alicyclic structure.
3. The curable resin composition according to claim 1 or 2, further comprising a crosslinking agent (X), wherein the content of the crosslinking agent (X) is 0.4 mass% or more and 10 mass% or less based on the total amount of the curable resin composition.
4. The curable resin composition according to claim 3, wherein the crosslinking agent (X) is a compound having an isocyanate group.
5. The curable resin composition according to claim 1, wherein the content of the compound B1 is 10% by mass or more and 50% by mass or less based on the total amount of the photopolymerizable compound B.
6. The curable resin composition according to claim 1 or 5, wherein the content of the compound B1 is 2.5% by mass or more and 15% by mass or less based on the total amount of the curable resin composition.
7. The curable resin composition according to claim 1 or 5, wherein the photopolymerizable compound B comprises a (meth) acrylic compound having an alicyclic structure.
8. The curable resin composition according to claim 1 or 5, wherein the photopolymerizable compound B contains a compound B2 having a glass transition temperature (Tg) after formation of a homopolymer of less than 70 ℃.
9. The curable resin composition according to claim 1 or 2, wherein the moisture-curable resin (a) is a moisture-curable urethane resin.
10. The curable resin composition according to claim 1 or 2, wherein the moisture-curable resin (A) is contained in an amount of 50 mass% or more and 80 mass% or less based on the total amount of the curable resin composition.
11. A cured product of the curable resin composition according to any one of claims 1 to 10.
12. An electronic component comprising the cured product according to claim 11.
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| PCT/JP2020/021246 WO2020241803A1 (en) | 2019-05-30 | 2020-05-28 | Curable resin composition, cured object, and electronic component |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2008133460A (en) * | 2006-10-27 | 2008-06-12 | Asahi Glass Co Ltd | Method for producing urethane resin for vibration damping material and urethane prepolymer for vibration damping material |
| CN107108772A (en) * | 2015-04-17 | 2017-08-29 | 积水化学工业株式会社 | Firming body, electronic unit, display element and light wet-cured type resin combination |
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| JP5109157B2 (en) * | 2007-02-26 | 2012-12-26 | 旭硝子株式会社 | Polyurethane-based curable composition |
| JP6660545B2 (en) | 2014-12-16 | 2020-03-11 | Dic株式会社 | Moisture-curable hot melt urethane composition and adhesive |
| JP2019199544A (en) * | 2018-05-16 | 2019-11-21 | 宇部興産株式会社 | Resin composition, cured product, civil engineering and construction structure, and coating method |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008133460A (en) * | 2006-10-27 | 2008-06-12 | Asahi Glass Co Ltd | Method for producing urethane resin for vibration damping material and urethane prepolymer for vibration damping material |
| CN107108772A (en) * | 2015-04-17 | 2017-08-29 | 积水化学工业株式会社 | Firming body, electronic unit, display element and light wet-cured type resin combination |
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| TW202110925A (en) | 2021-03-16 |
| CN117903706A (en) | 2024-04-19 |
| WO2020241803A1 (en) | 2020-12-03 |
| JPWO2020241803A1 (en) | 2020-12-03 |
| CN113557277A (en) | 2021-10-26 |
| KR20220016023A (en) | 2022-02-08 |
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