CN114761460B - Cation-curable composition, cured product, and joined body - Google Patents
Cation-curable composition, cured product, and joined body Download PDFInfo
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- CN114761460B CN114761460B CN202080084621.6A CN202080084621A CN114761460B CN 114761460 B CN114761460 B CN 114761460B CN 202080084621 A CN202080084621 A CN 202080084621A CN 114761460 B CN114761460 B CN 114761460B
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- 239000000203 mixture Substances 0.000 title claims abstract description 109
- 239000003822 epoxy resin Substances 0.000 claims abstract description 65
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 65
- 238000010538 cationic polymerization reaction Methods 0.000 claims abstract description 35
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 35
- 125000003118 aryl group Chemical group 0.000 claims abstract description 34
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 27
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 27
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 18
- 229920001610 polycaprolactone Polymers 0.000 claims abstract description 11
- 239000004632 polycaprolactone Substances 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 229920005862 polyol Polymers 0.000 claims abstract description 9
- 150000003077 polyols Chemical class 0.000 claims abstract description 9
- -1 amine salt Chemical class 0.000 claims description 59
- 125000002091 cationic group Chemical group 0.000 claims description 37
- 239000000853 adhesive Substances 0.000 claims description 19
- 230000001070 adhesive effect Effects 0.000 claims description 19
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 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 claims description 11
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 claims description 8
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 8
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 7
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 6
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 claims description 4
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 claims description 4
- 239000004843 novolac epoxy resin Substances 0.000 claims description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 4
- YQMXOIAIYXXXEE-UHFFFAOYSA-N 1-benzylpyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CC=CC=C1 YQMXOIAIYXXXEE-UHFFFAOYSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- NIYNIOYNNFXGFN-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol;7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound OCC1CCC(CO)CC1.C1C(C(=O)O)CCC2OC21.C1C(C(=O)O)CCC2OC21 NIYNIOYNNFXGFN-UHFFFAOYSA-N 0.000 claims description 3
- IDSLNGDJQFVDPQ-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-yl) hexanedioate Chemical compound C1CC2OC2CC1OC(=O)CCCCC(=O)OC1CC2OC2CC1 IDSLNGDJQFVDPQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004841 bisphenol A epoxy resin Substances 0.000 claims description 3
- 239000004842 bisphenol F epoxy resin Substances 0.000 claims description 3
- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims description 2
- 150000001896 cresols Chemical class 0.000 claims description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 abstract description 11
- 239000004734 Polyphenylene sulfide Substances 0.000 description 26
- 229920000069 polyphenylene sulfide Polymers 0.000 description 26
- 239000000047 product Substances 0.000 description 24
- 230000000052 comparative effect Effects 0.000 description 19
- 238000012360 testing method Methods 0.000 description 16
- 239000006087 Silane Coupling Agent Substances 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 238000001723 curing Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 7
- FNYWFRSQRHGKJT-UHFFFAOYSA-N 3-ethyl-3-[(3-ethyloxetan-3-yl)methoxymethyl]oxetane Chemical compound C1OCC1(CC)COCC1(CC)COC1 FNYWFRSQRHGKJT-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000004512 die casting Methods 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- URSLCTBXQMKCFE-UHFFFAOYSA-N dihydrogenborate Chemical compound OB(O)[O-] URSLCTBXQMKCFE-UHFFFAOYSA-N 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000011342 resin composition Substances 0.000 description 3
- LTOKKZDSYQQAHL-UHFFFAOYSA-N trimethoxy-[4-(oxiran-2-yl)butyl]silane Chemical compound CO[Si](OC)(OC)CCCCC1CO1 LTOKKZDSYQQAHL-UHFFFAOYSA-N 0.000 description 3
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 2
- QKAIFCSOWIMRJG-UHFFFAOYSA-N (4-methylphenyl)-(4-propan-2-ylphenyl)iodanium Chemical compound C1=CC(C(C)C)=CC=C1[I+]C1=CC=C(C)C=C1 QKAIFCSOWIMRJG-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- BIDWUUDRRVHZLQ-UHFFFAOYSA-N 3-ethyl-3-(2-ethylhexoxymethyl)oxetane Chemical compound CCCCC(CC)COCC1(CC)COC1 BIDWUUDRRVHZLQ-UHFFFAOYSA-N 0.000 description 2
- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical compound OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 description 2
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- SBQIJPBUMNWUKN-UHFFFAOYSA-M diphenyliodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=CC=CC=1[I+]C1=CC=CC=C1 SBQIJPBUMNWUKN-UHFFFAOYSA-M 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000007602 hot air drying Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002921 oxetanes Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 238000004382 potting Methods 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- HHPPHUYKUOAWJV-UHFFFAOYSA-N triethoxy-[4-(oxiran-2-yl)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCCC1CO1 HHPPHUYKUOAWJV-UHFFFAOYSA-N 0.000 description 2
- ZZJNLOGMYQURDL-UHFFFAOYSA-M trifluoromethanesulfonate;tris(4-methylphenyl)sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(C)=CC=C1[S+](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZZJNLOGMYQURDL-UHFFFAOYSA-M 0.000 description 2
- 229960000834 vinyl ether Drugs 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 description 1
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 description 1
- MWZJGRDWJVHRDV-UHFFFAOYSA-N 1,4-bis(ethenoxy)butane Chemical compound C=COCCCCOC=C MWZJGRDWJVHRDV-UHFFFAOYSA-N 0.000 description 1
- DQNSRQYYCSXZDF-UHFFFAOYSA-N 1,4-bis(ethenoxymethyl)cyclohexane Chemical compound C=COCC1CCC(COC=C)CC1 DQNSRQYYCSXZDF-UHFFFAOYSA-N 0.000 description 1
- UEIPWOFSKAZYJO-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-[2-(2-ethenoxyethoxy)ethoxy]ethane Chemical compound C=COCCOCCOCCOCCOC=C UEIPWOFSKAZYJO-UHFFFAOYSA-N 0.000 description 1
- IBASEVZORZFIIH-UHFFFAOYSA-N 1-(9h-fluoren-2-yl)ethanone Chemical compound C1=CC=C2C3=CC=C(C(=O)C)C=C3CC2=C1 IBASEVZORZFIIH-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
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- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- LZHUBCULTHIFNO-UHFFFAOYSA-N 2,4-dihydroxy-1,5-bis[4-(2-hydroxyethoxy)phenyl]-2,4-dimethylpentan-3-one Chemical compound C=1C=C(OCCO)C=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=C(OCCO)C=C1 LZHUBCULTHIFNO-UHFFFAOYSA-N 0.000 description 1
- AVXFJPFSWLMKSG-UHFFFAOYSA-N 2,7-dibromo-9h-fluorene Chemical compound BrC1=CC=C2C3=CC=C(Br)C=C3CC2=C1 AVXFJPFSWLMKSG-UHFFFAOYSA-N 0.000 description 1
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- FWLHAQYOFMQTHQ-UHFFFAOYSA-N 2-N-[8-[[8-(4-aminoanilino)-10-phenylphenazin-10-ium-2-yl]amino]-10-phenylphenazin-10-ium-2-yl]-8-N,10-diphenylphenazin-10-ium-2,8-diamine hydroxy-oxido-dioxochromium Chemical compound O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.Nc1ccc(Nc2ccc3nc4ccc(Nc5ccc6nc7ccc(Nc8ccc9nc%10ccc(Nc%11ccccc%11)cc%10[n+](-c%10ccccc%10)c9c8)cc7[n+](-c7ccccc7)c6c5)cc4[n+](-c4ccccc4)c3c2)cc1 FWLHAQYOFMQTHQ-UHFFFAOYSA-N 0.000 description 1
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- SNAGVRNJNARVRV-UHFFFAOYSA-N 2-[(3-ethyloxetan-3-yl)methoxymethyl]oxolane Chemical compound C1CCOC1COCC1(CC)COC1 SNAGVRNJNARVRV-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FXSCJZNMWILAJO-UHFFFAOYSA-N 2-bromo-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(Br)C=C3CC2=C1 FXSCJZNMWILAJO-UHFFFAOYSA-N 0.000 description 1
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- VNYQUOAQPXGXQO-UHFFFAOYSA-N 2-iodo-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(I)C=C3CC2=C1 VNYQUOAQPXGXQO-UHFFFAOYSA-N 0.000 description 1
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- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
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- PWGAXPBJOGFFMY-UHFFFAOYSA-N 3-ethyl-3-(2-methylpropoxymethoxymethyl)oxetane Chemical compound CC(C)COCOCC1(CC)COC1 PWGAXPBJOGFFMY-UHFFFAOYSA-N 0.000 description 1
- DILMQZOSIJKYHA-UHFFFAOYSA-N 3-ethyl-3-[(2,3,4,5,6-pentabromophenoxy)methyl]oxetane Chemical compound BrC=1C(Br)=C(Br)C(Br)=C(Br)C=1OCC1(CC)COC1 DILMQZOSIJKYHA-UHFFFAOYSA-N 0.000 description 1
- FQUZJULGTSCUDF-UHFFFAOYSA-N 3-ethyl-3-[(2,3,4,5,6-pentachlorophenoxy)methyl]oxetane Chemical compound ClC=1C(Cl)=C(Cl)C(Cl)=C(Cl)C=1OCC1(CC)COC1 FQUZJULGTSCUDF-UHFFFAOYSA-N 0.000 description 1
- RPPXSOMTWKENLK-UHFFFAOYSA-N 3-ethyl-3-[(2-methylphenyl)methyl]oxetane Chemical compound C=1C=CC=C(C)C=1CC1(CC)COC1 RPPXSOMTWKENLK-UHFFFAOYSA-N 0.000 description 1
- WUGFSEWXAWXRTM-UHFFFAOYSA-N 3-ethyl-3-[2-[2-[2-[2-[(3-ethyloxetan-3-yl)methoxy]ethoxy]ethoxy]ethoxy]ethoxymethyl]oxetane Chemical compound C1OCC1(CC)COCCOCCOCCOCCOCC1(CC)COC1 WUGFSEWXAWXRTM-UHFFFAOYSA-N 0.000 description 1
- HPINXYMPRYQBGF-UHFFFAOYSA-N 3-ethyl-3-[[3-[(3-ethyloxetan-3-yl)methoxy]-2,2-bis[(3-ethyloxetan-3-yl)methoxymethyl]propoxy]methyl]oxetane Chemical compound C1OCC1(CC)COCC(COCC1(CC)COC1)(COCC1(CC)COC1)COCC1(CC)COC1 HPINXYMPRYQBGF-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- 125000004864 4-thiomethylphenyl group Chemical group 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- YIEDFHHVUWKOEV-UHFFFAOYSA-N 6-methyl-3-(3-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound CC1OC1C1CC2OC2(C)CC1 YIEDFHHVUWKOEV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CFRFHWQYWJMEJN-UHFFFAOYSA-N 9h-fluoren-2-amine Chemical compound C1=CC=C2C3=CC=C(N)C=C3CC2=C1 CFRFHWQYWJMEJN-UHFFFAOYSA-N 0.000 description 1
- SYKJOJSYQSVNOM-UHFFFAOYSA-N 9h-fluoren-9-ylazanium;chloride Chemical compound Cl.C1=CC=C2C(N)C3=CC=CC=C3C2=C1 SYKJOJSYQSVNOM-UHFFFAOYSA-N 0.000 description 1
- XXSCONYSQQLHTH-UHFFFAOYSA-N 9h-fluoren-9-ylmethanol Chemical compound C1=CC=C2C(CO)C3=CC=CC=C3C2=C1 XXSCONYSQQLHTH-UHFFFAOYSA-N 0.000 description 1
- SNCJAJRILVFXAE-UHFFFAOYSA-N 9h-fluorene-2,7-diamine Chemical compound NC1=CC=C2C3=CC=C(N)C=C3CC2=C1 SNCJAJRILVFXAE-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 239000004643 cyanate ester Substances 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- HBRBERJSXNTAGV-UHFFFAOYSA-N diethoxy-methyl-[4-(oxiran-2-yl)butyl]silane Chemical compound CCO[Si](C)(OCC)CCCCC1CO1 HBRBERJSXNTAGV-UHFFFAOYSA-N 0.000 description 1
- LMQORFSQFKHATF-UHFFFAOYSA-N dimethoxy-methyl-[4-(oxiran-2-yl)butyl]silane Chemical compound CO[Si](C)(OC)CCCCC1CO1 LMQORFSQFKHATF-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- AFMVESZOYKHDBJ-UHFFFAOYSA-N fluoren-9-ol Chemical compound C1=CC=C2C(O)C3=CC=CC=C3C2=C1 AFMVESZOYKHDBJ-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- HEQBUZNAOJCRSL-UHFFFAOYSA-N iron(ii) chromite Chemical compound [O-2].[O-2].[O-2].[Cr+3].[Fe+3] HEQBUZNAOJCRSL-UHFFFAOYSA-N 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
-
- 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
- C09J11/06—Non-macromolecular additives organic
-
- 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
Abstract
The purpose of the present invention is to provide a cationically curable composition that has excellent adhesion to aluminum die-cast articles, PPS, and the like while maintaining photocurability and low-temperature curability. The cation curable composition of the present invention contains the following components (A) to (E), and contains 12 to 100 parts by mass of the component (E) per 100 parts by mass of the total amount of the components (A) and (B). Component (A): an aromatic epoxy resin; component (B): at least one of a hydrogenated epoxy resin (B1) and an alicyclic epoxy resin (B2); component (C): a photo-cationic polymerization initiator; and (D) component: a thermal cationic polymerization initiator; component (E): polycaprolactone polyols having hydroxyl groups above 3 functions (including 3 functions) and having a molecular weight of 1700 or less (including 1700).
Description
Technical Field
The invention relates to a cationically curable composition, a cured product, and a joined body.
Background
Conventionally, a cationic curable composition containing an epoxy resin or the like has been used for various applications such as adhesives, sealants, potting agents, coating agents, and conductive adhesives because of its excellent adhesiveness, sealability, high strength, heat resistance, electrical characteristics, and chemical resistance. Further, the object is widely used in particular in electronic/electric devices, such as liquid crystal displays, flat panel displays such as organic electroluminescence and touch panels, hard disk devices, mobile terminal devices, semiconductors, camera modules, and the like.
JP-A59-204676 discloses a photo-cation polymerizable resin composition comprising an epoxy resin and a photo-cation polymerization initiator which generates a Lewis acid upon irradiation with an active energy ray such as ultraviolet rays. Further, in international publication No. 2005/059002 (corresponding to the specification of U.S. patent application publication No. 2007/0208106), a cationically curable epoxy resin composition is disclosed, which contains an epoxy resin component, a photo cation polymerization initiator, a thermal cation polymerization initiator, and a filler.
Disclosure of Invention
However, the cationic polymerizable resin composition disclosed in Japanese unexamined patent publication No. 59-204676 has a problem that it cannot be cured in a place not exposed to light. In order to solve this problem, when heated to about 200 ℃, an acid can be generated from a cationic initiator and cured, but the curing condition is high temperature, and therefore it is difficult to apply the composition to applications such as liquid crystal display elements and organic EL elements which are easily degraded by heat. On the other hand, in the cationic curable epoxy resin composition disclosed in international publication No. 2005/059002 (corresponding to U.S. patent application publication No. 2007/0208106), although the thermal cationic polymerization initiator has been improved so as to be curable at a relatively low temperature in the unexposed portion, the composition is inferior in adhesion to an electronic/electric part module, an aluminum die cast material which is generally used as a material of an automobile part, polyphenylene sulfide (PPS) or the like.
The present invention has been made to solve the above-mentioned problems, and an object of the present invention is to provide a cationic curable composition having excellent adhesion to aluminum die-cast products, PPS, and the like while maintaining photocurability and low-temperature curability.
The present invention overcomes the above-described conventional problems, namely, the present invention has the following gist.
[1] A cationically curable composition comprising the following components (A) to (E) and containing 12 to 100 parts by mass of the component (E) per 100 parts by mass of the total amount of the components (A) and (B),
(A) The components are as follows: aromatic epoxy resin
(B) The components are as follows: at least one kind selected from the group consisting of hydrogenated epoxy resins (B1) and alicyclic epoxy resins (B2)
(C) The components are as follows: photo cation polymerization initiator
(D) The components are as follows: thermal cationic polymerization initiator
(E) The components are as follows: polycaprolactone polyols having hydroxyl groups above 3 functions (including 3 functions) and having a molecular weight of 1700 or less (including 1700).
[2] The cationic curable composition according to the above [1], wherein the content of the component (B) is 10 to 80 parts by mass based on 100 parts by mass of the total amount of the component (A) and the component (B).
[3] The cationic curable composition according to the above [1] or [2], wherein the component (D) is at least 1 selected from the group consisting of an aromatic sulfonium-based thermal cationic polymerization initiator, an aromatic iodonium-based thermal cationic polymerization initiator, and a thermal cationic polymerization initiator containing an amine salt.
[4] The cationic curable composition according to any one of [1] to [3], wherein the component (D) contains a thermal cationic polymerization initiator having a salt of a quaternary ammonium cation.
[5] The cationic curable composition according to any one of [1] to [4], wherein the component (C) contains at least one of an aromatic iodonium salt and an aromatic sulfonium salt.
[6] The cationic curable composition according to any one of [1] to [5], wherein the component (A) comprises at least 1 selected from the group consisting of an aromatic bisphenol A type epoxy resin, an aromatic bisphenol F type epoxy resin, and an aromatic bisphenol E type epoxy resin.
[7] The cationic curable composition according to any one of [1] to [6], wherein the component (B) comprises only any one of the hydrogenated epoxy resin (B1) and the alicyclic epoxy resin (B2).
[8] The cationic curable composition according to any one of the above [1] to [6], wherein the component (B) comprises a hydrogenated epoxy resin (B1) and an alicyclic epoxy resin (B2).
[9] The cation curable composition according to any one of the above [1] to [8], which is used for an adhesive.
[10] The cation curable composition according to any one of the above [1] to [8], which is used as an adhesive in the case where an adherend is an aluminum die-cast or PPS.
[11] A cured product of the cationic curable composition according to any one of [1] to [10 ].
[12] A bonded body obtained by bonding an adherend with the cationically curable composition according to any one of [1] to [10 ].
Detailed Description
The present invention will be described in detail below. In the present specification, "X to Y" are used to indicate values (X and Y) described before and after the values as a lower limit value and an upper limit value, and refer to "X or more (including X) and Y or less (including Y)".
Cationic curable composition
The components (a) to (E) contained in the cationically curable composition of the invention are as follows.
(A) The components are as follows: aromatic epoxy resin
(B) The components are as follows: at least one of hydrogenated epoxy resin (B1) and alicyclic epoxy resin (B2)
(C) The components are as follows: photo cation polymerization initiator
(D) The components are as follows: thermal cationic polymerization initiator
(E) The components are as follows: polycaprolactone polyols having hydroxyl groups above 3 functions (including 3 functions) and having a molecular weight below 1500 (including 1500).
Component (A)
The aromatic epoxy resin of the component (a) of the present invention refers to a compound that undergoes a crosslinking reaction with a cationic species generated by a cationic polymerization initiator by irradiation or heating with active energy rays. (A) The kind of the component is not particularly limited, and examples thereof include: an aromatic bisphenol a type epoxy resin, an aromatic bisphenol F type epoxy resin, an aromatic bisphenol E type epoxy resin, a diglycidyl ether of an aromatic bisphenol a type alkylene oxide adduct, a diglycidyl ether of an aromatic bisphenol F type alkylene oxide adduct, a diglycidyl ether of an aromatic bisphenol E type alkylene oxide adduct, an aromatic novolac type epoxy resin, a urethane modified aromatic epoxy resin, a nitrogen-containing aromatic epoxy resin, a rubber modified aromatic epoxy resin containing polybutadiene or Nitrile Butadiene Rubber (NBR), and the like. Among these, from the viewpoint of obtaining a cationic curable composition excellent in adhesion to aluminum die-cast products, PPS, and the like, an aromatic bisphenol a type epoxy resin, an aromatic bisphenol F type epoxy resin, or an aromatic bisphenol E type epoxy resin is preferable.
Examples of commercial products of aromatic epoxy resins include, for example: jER (registered trademark, also referred to below) 825, jER827, jER828EL, jER828US, jER828XA, jER834, jER806H, jER, jER807ST, jER604, jER630 (manufactured above by Mitsubishi chemical corporation); EPICLON (registered trademark, the same applies hereinafter) 830, EPICLONEXA-830LVP, EPICLONEXA-850CRP, EPICLON835LV, EPICLONHP4032D, EPICLON, EPICLON720, EPICLON726, EPICLONHP820, EPICLONN-660, EPICLONN-680, EPICLON-695, EPICLONN-655-EXP-S, EPICLONN-665-EXP-S, EPICLONN-685-EXP-S, EPICLONN-740, EPICLONN-775, EPICLONN-865 (manufactured by DIC Co., ltd.); ADEKARESIN (registered trademark, the same applies hereinafter) EP4100, ADEKARESINEP4000, ADEKARESINEP4080, ADEKARESINEP4085, ADEKARESINEP4088, ADEKARESINEP4100HF, ADEKARESINEP HF, ADEKARESINEP4000S, ADEKARESINEP4000L, ADEKARESINEP4003S, ADEKARESINEP4010S, ADEKARESINEP4010L (manufactured by ADEKA corporation, above); DENACOL (registered trademark, the same applies hereinafter) EX-614B, DENACOLEX-411, DENACOLEX-314, DENACOLEX-201, DENACOLEX-212, DENACOLEX-252 (manufactured by Nagase Chemte X Co., ltd.) and the like, but are not limited thereto. These aromatic epoxy resins may be used alone or in combination of 2 or more (including 2).
Component (B)
The component (B) of the present invention is at least one compound selected from the group consisting of a hydrogenated epoxy resin (B1) and an alicyclic epoxy resin (B2), and is a compound which causes a crosslinking reaction by irradiation or heating of a cationic species generated by a cationic polymerization initiator. The hydrogenated epoxy resin (B1) and the alicyclic epoxy resin (B2) may be used alone, or the hydrogenated epoxy resin (B1) and the alicyclic epoxy resin (B2) may be used in combination. The hydrogenated epoxy resin (B1) and the alicyclic epoxy resin (B2) are preferable because they have more excellent adhesion to aluminum die-cast articles when used alone. When these are used in combination, the balance between the photocurability and the low-temperature curability is excellent, and the adhesion to each member is preferably maintained. The hydrogenated epoxy resin (B1) is a compound having no unsaturated bond, which is obtained by core-hydrogenating an aromatic ring of an aromatic epoxy resin.
The type of the hydrogenated epoxy resin (B1) is not particularly limited, and examples thereof include: hydrogenated bisphenol A type epoxy resin, hydrogenated bisphenol F type epoxy resin, hydrogenated bisphenol E type epoxy resin, diglycidyl ether of hydrogenated bisphenol A type alkylene oxide adduct, diglycidyl ether of hydrogenated bisphenol F type alkylene oxide adduct, hydrogenated phenol novolac epoxy resin, hydrogenated cresol novolac epoxy resin, and the like. Among these, hydrogenated bisphenol a epoxy resin, hydrogenated bisphenol F epoxy resin, or hydrogenated bisphenol E epoxy resin is preferable from the viewpoint of obtaining a cationic curable composition excellent in adhesion to aluminum die-cast products, PPS, and the like.
Examples of commercial products of hydrogenated bisphenol a epoxy resins include: jERYX-8000, jERYX-8034 (manufactured by Mitsubishi chemical Co., ltd.); EPICLONEXA-7015 (manufactured by DIC Co., ltd.); ST-3000 (manufactured by Nissan chemical materials Co., ltd.); RIKARESINHBE-100 (manufactured by New Kagaku chemical Co., ltd.); DENACOLEX-252 (manufactured by NagaseChemteX Co., ltd.) and the like. Further, examples of commercial products of hydrogenated bisphenol F epoxy resins include: YL-6753 (manufactured by Mitsubishi chemical corporation), and the like.
The alicyclic epoxy resin (B2) may be a compound having a functional group represented by the following formula (1). More specific examples include, but are not limited to, for example: 3, 4-epoxycyclohexylmethyl (3 ',4' -epoxycyclohexane carboxylate, epsilon-caprolactone-modified 3',4' -epoxycyclohexylmethyl, 3, 4-epoxycyclohexane carboxylate, bis (3, 4-epoxycyclohexyl) adipate, 1, 2-epoxy4-vinylcyclohexane, 1, 4-cyclohexanedimethanol diglycidyl ether, epoxyethyldivinyl cyclohexane, diglycidyl vinylcyclohexane, 1,2, 4-trioxyethylcyclohexane, limonene dioxide, alicyclic epoxy-containing siloxane oligomers, and the like. Among these, 3, 4-epoxycyclohexylmethyl (3 ',4' -epoxycyclohexane carboxylate), epsilon-caprolactone-modified 3',4' -epoxycyclohexylmethyl, 3, 4-epoxycyclohexane carboxylate, bis (3, 4-epoxycyclohexyl) adipate, 1, 2-epoxy-4-vinylcyclohexane, or 1, 4-cyclohexanedimethanol diglycidyl ether are preferable from the viewpoint of obtaining a cationically curable composition excellent in adhesion to aluminum die-cast, PPS, or the like.
The commercial product of the alicyclic epoxy resin (B2) is not particularly limited, and examples thereof include: CELLOXIDE 2081 (3 ',4' -epoxycyclohexylmethyl 3, 4-epoxycyclohexane carboxylate), CELLOXIDE 2021P (3 ',4' -epoxycyclohexylmethyl 3, 4-epoxycyclohexane carboxylate), CELLOXIDE 2000 (1, 2-epoxy-4-vinylcyclohexane), CELLOXIDE 3000 (1-methyl-4- (2-methyl-epoxyethyl) -7-oxabicyclo [4.1.0] heptane), EHPE3150 (1, 2-epoxy-4- (2-epoxyethyl) cyclohexane adduct of 2, 2-bis (hydroxymethyl) -1-butanol) (manufactured above by Daicel corporation); TTA21 (manufactured by Jiangsu Taike chemical Co., ltd.); x-40-2670, X-22-169AS, X-22-169B (manufactured by Xinyue chemical industries Co., ltd.) and the like, but is not limited thereto.
(B) The amount of the component (A) to be added is not particularly limited, but is preferably 10 to 95 parts by mass, more preferably 20 to 90 parts by mass, and even more preferably 30 to 85 parts by mass, based on 100 parts by mass of the total amount of the component (A) and the component (B). The amount of the hydrogenated epoxy resin to be added to the component (A) is not particularly limited, but is preferably in the range of 50 to 700 parts by mass, more preferably in the range of 100 to 600 parts by mass, and even more preferably in the range of 150 to 550 parts by mass. The amount of the alicyclic epoxy resin to be added to the component (A) is not particularly limited, but is preferably in the range of 20 to 300 parts by mass, more preferably in the range of 50 to 250 parts by mass, and even more preferably in the range of 70 to 200 parts by mass, relative to 100 parts by mass of the component (B). When the amount of the component (B) is within the above range, a cationic curable composition having more excellent adhesion to aluminum die-cast products, PPS, and the like can be provided.
When the hydrogenated epoxy resin (B1) and the alicyclic epoxy resin (B2) are used together as the component (B), the amount of the alicyclic epoxy resin (B2) to be used is preferably 10 to 300 parts by mass, more preferably 30 to 150 parts by mass, and even more preferably 40 to 100 parts by mass, based on 100 parts by mass of the hydrogenated epoxy resin (B1). When the hydrogenated epoxy resin (B1) and the alicyclic epoxy resin (B2) are used together as the component (B), the ratio of the component (a) to the component (B) is as described above. (B1) When the amounts of the component (a) and the component (B2) used are within the above ranges, the balance between the photocurability and the low-temperature curability is good, and the proper adhesion to various members can be maintained.
Component (C)
The component (C) of the present invention is a photo-cationic polymerization initiator, which generates a cationic species upon irradiation with active energy rays. The type of the component (C) is not particularly limited, and examples thereof include: onium salts such as aromatic sulfonium salts and aromatic iodonium salts. (C) The components may be used alone or in combination of 2 or more (including 2). The cationic polymerization initiator having activity in both active energy rays and heat is regarded as component (C) in the present invention.
Examples of the aromatic iodonium salt include: the 2 groups bound to the iodine atom are salts of aryl groups containing iodonium. More specifically, for example, there may be mentioned: diphenyliodonium tetrakis (pentafluorophenyl) borate, diphenylhexafluorophosphate, diphenyliodonium hexafluoroantimonate, bis (4-nonylphenyl) hexafluorophosphate, 4-methylphenyl-4- (1-methylethyl) phenyliodonium tetrakis (pentafluorophenyl) borate, and the like.
Examples of the commercial product of the aromatic iodonium salt include: omnicat (registered trademark) 250 (manufactured by igmrensbv corporation); bluesilPI2074 (4-methylphenyl-4- (1-methylethyl) phenyliodonium tetrakis (pentafluorophenyl) borate, manufactured by Rhodia Co.); b2380 (bis (4-three butyl phenyl) iodonium hexafluorophosphate), B2381, D2238, D2248, D2253, I0591 (above by Tokyo chemical industry Co., ltd.); WPI-113 (bis [ 4-n-alkyl (C10-13) phenyl ] iodohexafluorophosphate), WPI-116 (bis [ n-alkyl (C10-13) phenyl ] iodohexafluoroantimonate), WPI-169, WPI-170 (bis (4-tert-butylphenyl) iodohexafluorophosphate), WPI-124 (bis [ 4-n-alkyl (C10-13) phenyl ] iodotetrafluorophenylborate) (manufactured by Fuji film and Wako pure chemical industries, ltd.) and the like.
The aromatic sulfonium salt is a sulfonium ion in which all of 3 groups bonded to a sulfur atom are aryl groups. More specifically, for example, there may be mentioned: triphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium tetrakis (pentafluorophenyl) borate, 4 '-bis [ diphenyldihydrothio ] diphenylsulfide-bis hexafluorophosphate, 4' -bis [ bis (. Beta. -hydroxyethoxy) phenyldihydrothio ] diphenylsulfide-bis hexafluoroantimonate, 4 '-bis [ bis (. Beta. -hydroxyethoxy) phenyldihydrothio ] diphenylsulfide-bis hexafluorophosphate, 7- [ bis (p-tolyl) dihydrothio ] -2-isopropylthioxanthone hexafluoroantimonate, 7- [ bis (p-tolyl) hydrosulfide ] -2-isopropylthioxanthone tetrakis (pentafluorophenyl) borate, 4-phenylcarbonyl-4' -diphenyldihydrothio-diphenylsulfide-hexafluorophosphate, 4- (p-tert-butylphenylcarbonyl) -4 '-diphenyldihydrothio-hexafluoroantimonate, 4- (p-tert-butylphenylcarbonyl) -4' -bis (p-tolyl) dihydrothio-diphenylsulfide-tetrafluorophenyl) tetrakis (4-methylphenyl) sulfonium (4-methylphenyl) tetrafluoroborate, and the like. However, it is not limited to these. These aromatic sulfonium salts may be used alone or in combination of 2 or more (including 2).
Examples of commercial aromatic sulfonium salts include: adecaAkles (registered trademark, the same applies hereinafter) SP-150, adecaAklesSP-170, adecaAklesSP-172 (manufactured by ADEKA corporation, above); CPI-100P, CPI-101A, CPI-110B, CPI-200K, CPI-210S (manufactured by Supppro Co., ltd.); t1608, T1609, T2041 (tris (4-methylphenyl) sulfonium hexafluorophosphate), T2042 (tri-p-tolylsulfonium trifluoromethanesulfonate) (manufactured above by tokyo chemical industry co., ltd); cyracureUVI-6990, cyracureUVI-6974 (manufactured by UnionCarbide corporation), DTS-200 (manufactured by afforestation corporation), and the like.
The amount of component (C) blended in the cationically curable composition of the invention is not particularly limited, but is preferably in the range of 0.1 to 30 parts by mass, more preferably in the range of 0.5 to 15 parts by mass, relative to 100 parts by mass of the total amount of component (A) and component (B). When the content of the component (C) is 0.1 part by mass or more (including 0.1 part by mass) per 100 parts by mass of the total amount of the component (a) and the component (B), sufficient photocurability can be obtained, and when it is 30 parts by mass or less (including 30 parts by mass), it is preferable from the viewpoint of excellent adhesion to aluminum die-cast products, PPS, and the like.
Component (D)
The component (D) of the present invention is a compound which generates a cationic species by heating a thermal cationic polymerization initiator. The type thereof is not particularly limited, and examples thereof include: among them, the thermal cationic polymerization initiator containing an amine salt is preferable from the viewpoint that a cationic curable composition excellent in adhesion to aluminum die-cast products, PPS, and the like while maintaining photocurability and low-temperature curability can be obtained. These may be used alone or in combination of 2 or more (including 2).
Examples of the thermal cationic polymerization initiator containing an amine salt include: a thermal cationic polymerization initiator comprising a salt having a quaternary ammonium cation, and the like. As more specific salts having quaternary ammonium cations, there may be mentioned, for example: salts of quaternary ammonium cations and borate anions, salts of quaternary ammonium cations and antimonate anions, salts of quaternary ammonium cations and phosphate anions, and the like. Among these, salts of quaternary ammonium cations and borate anions or salts of quaternary ammonium cations and antimonate anions are preferable from the viewpoint of excellent adhesion to aluminum die-cast products, PPS, and the like.
Examples of the borate anion include: tetrafluoroborate anions, tetrakis (perfluorophenyl) borate anions, and the like. Examples of the antimony anions include: tetrafluoroantimonate anions, tetrakis (perfluorophenyl) antimonate anions, and the like. Examples of the phosphate anions include: hexafluorophosphate anions, trifluoro [ tris (perfluoroethyl) ] and the like.
Examples of the commercial products of the thermal cationic polymerization initiator containing an amine salt include: K-PURE (registered trademark, the same applies hereinafter) CXC-1612 (thermal cation polymerization initiator made by King industries, inc. containing a salt of a quaternary ammonium cation and a borate anion), K-PURECEC-1821 (thermal cation polymerization initiator made by King industries, inc. containing a salt of a quaternary ammonium cation and an antimonate anion), and the like.
Examples of commercial products of the aromatic sulfonium-based thermal cationic polymerization initiator include: sanAid (registered trademark, the same applies hereinafter) SI-60, sanAidSI-60L, sanAidSI-80, sanAidSI-80L, sanAidSI-100, sanAidSI-100L, sanAidSI-180L, sanAidSI-B2A, sanAidSI-B3A (manufactured by SanXin chemical industry Co., ltd.); CI-2624 (manufactured by Nippon Caesarean Co., ltd.), and the like. Examples of the aromatic iodonium thermal cationic polymerization initiator include: diphenyliodonium triflate (reagent), and the like.
The amount of component (D) blended in the cationically curable composition of the invention is not particularly limited, but is preferably in the range of 0.1 to 30 parts by mass, more preferably in the range of 0.5 to 15 parts by mass, relative to 100 parts by mass of the total amount of component (a) and component (B). The amount of component (D) is preferably 0.1 part by mass or more (including 0.1 part by mass) based on 100 parts by mass of the total amount of component (a) and component (B), since the low-temperature curability is sufficient, and the adhesion to aluminum die-cast products, PPS, and the like is excellent when 30 parts by mass or less (including 30 parts by mass) is obtained.
Component (E)
The component (E) of the present invention is not particularly limited as long as it is a polycaprolactone polyol having a hydroxyl group of 3 or more functions (including 3 functions) and a molecular weight of 1700 or less (including 1700). The component (E) of the present invention can be combined with other components of the present invention, and by setting the component (E) in a blending range defined below, it can have a remarkable effect of excellent adhesion to aluminum die-cast products, PPS, and the like while maintaining photocurability and low-temperature curability. (E) The molecular weight of the component (A) is more preferably in the range of 200 to 1500, particularly preferably in the range of 250 to 1000. The determination of the molecular weight is according to JISK1557-1:2007, the measured value of the hydroxyl number of the polycaprolactone polyol.
The component (E) is not particularly limited, and examples thereof include: and a compound represented by the following general formula (2).
R-[O[CO(CH 2 ) 5 O] n H] m (2)
(wherein R is an aliphatic hydrocarbon group having a valence of 3 or 4, n is in the range of 2 to 500, and m is 3 or 4.)
(E) Specific compounds of the components can be exemplified by: polycaprolactone triol, polycaprolactone tetrol, and the like. Examples of the commercial products of the component (E) include: praxel (registered trademark, the same applies hereinafter) 303, praxel305, praxel308, praxel309, praxel312, praxel400 (manufactured by Daicel Co., ltd.), and the like.
The cation-curable composition of the present invention is characterized in that: the content of the component (E) is 12 to 100 parts by mass, preferably 15 to 70 parts by mass, more preferably 17 to 50 parts by mass, based on 100 parts by mass of the total amount of the component (A) and the component (B). In the above range, a cationically curable composition having excellent adhesion to aluminum die-cast products, PPS, and the like can be obtained while maintaining photocurability and low-temperature curability.
< arbitrary component >)
Further, the cation curable composition of the present invention may contain additives such as a silane coupling agent, a colorant, an oxetane compound, a vinyl ether compound, a sensitizer, a peroxide, a thiol compound, and a storage stabilizer in an amount suitable for the purpose of not impairing the characteristics of the present invention. Further, the cation curable composition of the present invention can be formulated in an appropriate amount within a range that does not impair the characteristics of the present invention: inorganic fillers having an average particle diameter of 0.001 to 100 μm, such as calcium carbonate, magnesium carbonate, titanium oxide, magnesium hydroxide, talc, silicon oxide, aluminum oxide, glass, aluminum hydroxide, boron nitride, aluminum nitride, and magnesium oxide; conductive particles such as silver: a flame retardant; rubber such as acrylic rubber and silicone rubber; a plasticizer and an organic solvent; antioxidants such as phenol antioxidants and phosphorus antioxidants; a light stabilizer; an ultraviolet absorber; a defoaming agent; a foaming agent; a release agent; a leveling agent; a rheology modifier; an adhesion promoter; a cure retarder; various additives such as polymers or thermoplastic elastomers, e.g., polyimide resins, polyamide resins, phenoxy resins, cyanate esters, poly (meth) acrylate resins, polyurethane resins, polyurea resins, polyester resins, polyvinyl butyral resins, styrene-butadiene-styrene copolymers (SBS), styrene-ethylene-butylene-styrene copolymers (SEBS), and the like. The addition of these components can provide a cationically curable composition excellent in resin strength, adhesive strength, flame retardancy, thermal conductivity, handleability, and the like, and a cured product thereof.
The silane coupling agent improves the compatibility of the components (a) to (E), and can provide a compound of a cationic curable composition excellent in adhesion to aluminum die-cast products, PPS, and the like, in addition to further improving the low-temperature curability. The silane coupling agent is not particularly limited, and specific examples thereof include: glycidyl group-containing silane coupling agents such as 3-glycidyl propyl triethoxysilane, 3-glycidyl propyl methyl dimethoxysilane, 3-glycidyl propyl trimethoxysilane, and 3-glycidyl propyl methyl diethoxysilane; vinyl-containing silane coupling agents such as vinyltris (. Beta. -methoxyethoxy) silane, vinyltriethoxysilane, vinyltrimethoxysilane, and the like; silane coupling agents containing a (meth) acrylic group such as gamma-methacryloxypropyl trimethoxysilane; amino-containing silane coupling agents such as N- β - (aminoethyl) - γ -aminopropyl trimethoxysilane, γ -aminopropyl triethoxysilane, and N-phenyl- γ -aminopropyl trimethoxysilane; and other gamma-mercaptopropyl trimethoxysilane, gamma-chloropropyl trimethoxysilane, etc. Among these, glycidyl group-containing silane coupling agents are preferable, and among the glycidyl group-containing silane coupling agents, 3-glycidyl propyl trimethoxysilane and 3-glycidyl propyl triethoxysilane are preferable. These silane coupling agents may be used alone or in combination of 2 or more (including 2). The blending amount of the silane coupling agent is not particularly limited, but is preferably in the range of 0.1 to 30 parts by mass, more preferably in the range of 0.5 to 15 parts by mass, relative to 100 parts by mass of the total of the component (a) and the component (B).
Examples of the coloring agent include: pigments, dyes, and the like, among which pigments are preferred from the viewpoint of durability. Further, among pigments, black pigments are preferable from the viewpoint of excellent hiding properties. Examples of the black pigment include: carbon black, black titanium oxide, copper chrome black, cyanine black, aniline black, and the like. Among these, carbon black is preferable from the viewpoints of the covering property and dispersibility in the component (a) of the present invention. The amount of the colorant to be blended in the cationically curable composition of the invention is not particularly limited, but is preferably in the range of 0.01 to 30 parts by mass, more preferably in the range of 0.05 to 10 parts by mass, and even more preferably in the range of 0.1 to 5 parts by mass, relative to 100 parts by mass of the total amount of the component (a) and the component (B).
Examples of oxetane compounds include: 3-ethyl-3-hydroxymethyl oxetane, 3- (methyl) allyloxymethyl-3-ethyloxetane, (3-ethyl-3-oxetanylmethyl) methylbenzene, 4-fluoro- [1- (3-ethyl-3-oxetanylmethyl) methyl ] benzene, [1- (3-ethyl-3-oxetanylmethoxy) ethyl ] phenyl ether, isobutoxymethyl (3-ethyl-3-oxetanylmethyl) ether, 2-ethylhexyl (3-ethyl-3-oxetanylmethyl) ether, ethyldiglycol (3-ethyl-3-oxetanylmethyl) ether, tetrahydrofurfuryl (3-ethyl-3-oxetanylmethyl) ether, tetrabromophenyl (3-ethyl-3-oxetanylmethyl) ether, 2-tetrabromophenoxyethyl (3-ethyl-3-oxetanylmethyl) ether, pentachlorophenyl (3-ethyl-3-oxetanylmethyl) ether, pentabromophenyl (3-ethyl-3-oxetanylmethyl) ether, ethyleneglycol (3-ethyl-3-oxetanylmethyl) ether, bis (3-oxetanylmethyl) ether, tetraethyleneglycol bis (3-ethyl-3-oxetanylmethyl) ether, trimethylol propane tris (3-ethyl-3-oxetanylmethyl) ether, pentaerythritol tetrakis (3-ethyl-3-oxetanylmethyl) ether, dipentaerythritol tetrakis (3-ethyl-3-oxetanylmethyl) ether, ditrimethylol propane tetrakis (3-ethyl-3-oxetanylmethyl) ether, and the like. Examples of commercial products of oxetane compounds include: aronoxetane (registered trademark, the same applies hereinafter) OXT-212, aronoxetane OXT-221, aronoxetane OXT-213, aronoxetane OXT-101 (manufactured by Toyama Co., ltd.) and the like.
Examples of the vinyl ether compound include, for example: 1, 4-butanediol divinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, tetraethylene glycol divinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, 2-ethylhexyl vinyl ether, cyclohexyl vinyl ether, 2-hydroxyethyl vinyl ether, diethylene glycol monovinyl ether, 4-hydroxybutyl vinyl ether, 2- (2-ethyleneoxyethoxy) ethyl acrylate, 2- (2-ethyleneoxyethoxy) ethyl methacrylate, and the like. Examples of commercial products of vinyl ether compounds include: NPVE, IPVE, NBVE, IBVE, 2-EHVE, CHVE (manufactured by Nippon carbide industries Co., ltd.); HEVE, DEGV, HBVE (manufactured by Wan petro-chemical Co., ltd.); VEEA, VEEM (manufactured by nippon catalyst corporation, above), and the like.
Examples of the sensitizer include: 9-fluorenone, anthrone, dibenzocycloheptone, fluorene, 2-bromofluorene, 9-dimethylfluorene, 2-fluorofluorene, 2-iodofluorene, 2-fluorenamine, 9-fluorenol, 2, 7-dibromofluorene, 9-aminofluorene hydrochloride, 2, 7-diaminofluorene, 9' -spirobis [ 9H-fluorene ], 2-fluorenecarboxylaldehyde, 9-fluorenylmethanol, 2-acetylfluorene, diphenylketone, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropane-1-one, benzildimethylketal, 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxy-cyclohexyl-phenyl-ketone, 2-methyl-2-N-morpholino (4-thiomethylphenyl) propane-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl), 2-hydroxy-2-methyl-1- [4- (1-methyl) phenyl ] butanone, nitro-oligoacetone, and the like. The amount of sensitizer to be added is not particularly limited, and may be appropriately determined with reference to the absorption wavelength and molar absorptivity.
< curing method >)
The cationically curable composition of the present invention can be cured (photocurable) by irradiation with active energy rays. The cationically curable composition of the present invention can be cured under low temperature conditions (low temperature curability). The cationically curable composition of the invention can be cured under irradiation with active energy rays and at low temperature. Here, examples of the active energy ray include: ultraviolet, electron beam, visible light, and the like. The wavelength of the active energy ray is preferably 150 to 830nm, more preferably 200 to 600nm, and still more preferably 250 to 380nm.
The term "low temperature" means a temperature at which the cationically curable composition of the invention can be cured is low, and corresponds to the heating condition of the curing method of the cationically curable composition of the invention. The heating condition (curable temperature) is not particularly limited, and is, for example, a temperature of 45℃to 150℃preferably 45℃or more (including 45 ℃) to less than 150℃more preferably 50℃or more (including 50 ℃) to less than 140℃and further preferably 55℃or more (including 55 ℃) to less than 130 ℃. When the heat curing temperature is 45 ℃ or higher (including 45 ℃) and less than 150 ℃, the heating time is preferably in the range of 3 minutes or higher (including 3 minutes) and less than 5 hours, more preferably in the range of 10 minutes or higher (including 10 minutes) and 3 hours or lower (including 3 hours). The cationically curable composition of the invention can be cured by irradiation with active energy rays. The active energy ray in this case includes, for example: ultraviolet rays, electron beams, visible rays, and the like, however, are not particularly limited. The cumulative light amount of the active energy rays is, for example, 300 to 100000mJ/cm 2 Preferably 500 to 50000mJ/cm 2 More preferably 1000 to 10000mJ/cm 2 Further preferably 2000 to 5000mJ/cm 2 Particularly preferably 3000mJ/cm 2 . The wavelength of the active energy ray is preferably 150 to 830nm, more preferably 200 to 600nm, and still more preferably 250 to 380nm.
< bonding method >)
The cationically curable composition of the invention can be used for adhesion of adherends. Specific bonding methods include, for example: the method for bonding an adherend comprises the following step 1 of disposing the cation-curable composition of the present invention between a pair of adherends, step 2 of irradiating the cation-curable composition with active energy rays, and step 3 of heating the composition at a temperature of 45 ℃ or higher (including 45 ℃) and less than 150 ℃ after the irradiation. The steps are described below.
Step 1 the cation curable composition of the present invention is disposed between a pair of adherends. Specifically, for example: the cation-curable composition is placed by dropping or coating one adherend, and the other adherend is placed in the placed cation-curable composition, and the pair of adherends are placed in arbitrary alignment. For example, a known coating method using a sealing agent or an adhesive can be used for coating. Specific coating methods include, for example: dispensing, spraying, ink-jetting, screen printing, gravure printing, dip coating, spin coating, and the like are performed using an automatic coater. The adherend may use, for example: metals, glass, plastics, and the like, however, from the viewpoint of excellent compatibility with the cation-curable composition of the present invention, preferable examples include: aluminum die casting, PPS.
Step 2 the cation-curable composition prepared in step 1 is irradiated with an active energy ray to cure the cation-curable composition, and the pair of adherends are temporarily adhered. The curing of the cationically curable composition by irradiation with active energy rays is particularly carried out on the surface of the composition and in the vicinity thereof. The irradiation may be directly performed on the cation-curable composition to be disposed, and particularly, in the case where the adherend is transparent or translucent, the irradiation may be indirectly performed through the adherend.
Step 3 after the irradiation of the active energy rays of step 2, the disposed cationically curable composition is further heated at a predetermined temperature to completely cure the cationically curable composition and to completely bond (primary bond) the pair of adherends. The cationically curable composition is cured by heating, particularly in the interior of the composition, except at and near the surface of the composition. When the curing reaction by irradiation of step 2 is performed before the curing reaction by heating in step 3, the curing (crosslinking) reaction of the resin composition is rapidly started, and the curing reaction by heating in the subsequent step 3 is performed rapidly after the curing reaction in the cationic curable composition which is not exposed to active energy rays, thereby achieving complete curing of the cationic curable composition. The heating temperature in step 3 is preferably 45 to 150 ℃, more preferably 45 ℃ or higher (including 45 ℃) and less than 140 ℃, still more preferably 50 ℃ or higher (including 50 ℃) and less than 130 ℃, particularly preferably 55 ℃ or higher (including 55 ℃) and less than 125 ℃.
Use of cation-curable composition
The use of the cationically curable composition of the invention is not particularly limited, and examples thereof include: adhesive, sealant, coating agent, potting agent, conductive adhesive, etc. The field to which the cation-curable composition of the present invention can be applied is not particularly limited, and examples thereof include: automobile fields such as switch parts, headlamps, engine internal parts, electrical parts, driving engines, brake oil tanks and the like; flat panel display fields such as liquid crystal displays, organic electroluminescence, touch panels, plasma displays, light emitting diode display devices, and the like; recording fields such as video disks, CD, DVD, MD, imaging lenses, hard disk peripheral members, and blu-ray discs; electronic materials such as sealing materials for electronic components, circuits, relays, electrical contacts, and semiconductor devices, die attach agents, conductive adhesives, anisotropic conductive adhesives, and interlayer adhesives for multilayer substrates including laminated substrates; a CMOS image sensor and other photographic modules; battery fields such as lithium batteries, manganese batteries, alkaline batteries, nickel-based batteries, fuel cells, silicon-based solar batteries, dye-sensitized solar batteries, and organic solar batteries; optical parts such as optical switch periphery, optical connector periphery, optical passive parts, optical circuit parts, and photoelectric integrated circuit periphery in optical communication system; a mobile terminal device; building, aviation, etc.
The cationically curable composition of the present invention can be used as an adhesive for assembling electronic/electric component modules, automobile parts, etc., and is excellent in adhesion to aluminum die castings, PPS, etc., while maintaining photocurability and low-temperature curability. Examples of the electronic/electric component module include: display housing, computer housing, optical read head module, mobile machine housing, HDD housing, camera module, projector housing, CD, DVD player housing, heat sink, relay, connector, module case, etc. The vehicle parts include, for example: an ECU housing, a vehicle camera module, a vehicle sensor module (a vehicle radar module, a rider module, etc.), a condenser housing, a power module, a connector, an ignition coil, etc.
Examples (example)
The present invention will be specifically described below by way of examples, but the present invention is not limited by the following examples.
Preparation of cation-curable composition
EXAMPLE 1
20 parts by mass of an aromatic bisphenol F-type epoxy resin (a 1) (manufactured by Mitsubishi chemical Co., ltd.; jER807 ST) as a component (A) was blocked at room temperature (25 ℃ C.),
50 parts by mass of a hydrogenated bisphenol A-type epoxy resin (B1) (Mitsubishi chemical Co., ltd.; jERYX-8000) as a component (B), 30 parts by mass of 3',4' -epoxycyclohexylmethyl 3, 4-epoxycyclohexane carboxylate (B2) (Daicel Co., ltd.; celloxide 2021P),
3 parts by mass of 4-methylphenyl-4- (1-methylethyl) phenyliodonium-tetrakis (pentafluorophenyl) borate (C1) (manufactured by Rodia Co., ltd.; bluesilPI-2074) as a component (C),
2 parts by mass of a thermal cationic polymerization initiator (D1) (manufactured by King Industries Co., ltd.; K-PURECEC-1821) containing a salt comprising a quaternary ammonium cation and a borate anion as the component (D),
25 parts by mass of polycaprolactone triol (E1) having 3-functional hydroxyl groups and having a molecular weight of 550 (manufactured by Daicel Co., ltd.; placel 305) as the component (E),
2 parts by mass of 3-glycidyl propyl trimethoxy silane as a silane coupling agent,
added to a planetary mixer and mixed for 60 minutes to obtain a cationic curable composition of example 1.
EXAMPLE 2
In example 1, the same procedure as in example 1 was carried out except that 20 parts by mass of the component (a 1) was changed to 50 parts by mass, and 30 parts by mass of the component (b 2) was changed to 50 parts by mass, whereby a cationic curable composition of example 2 was obtained.
EXAMPLE 3
In example 1, the same procedure as in example 1 was carried out except that 50 parts by mass of the component (b 1) was changed to 80 parts by mass and the component (b 2) was not used, to obtain a cationic curable composition of example 3.
Comparative example 1
In example 1, the same procedure as in example 1 was carried out except that (a 1) was removed and 50 parts by mass of the component (b 1) was changed to 70 parts by mass, to prepare a cationically curable composition of comparative example 1.
Comparative example 2
In example 1, the same procedure as in example 1 was carried out except that (e 1) was removed, to prepare a cationic curable composition of comparative example 2.
Comparative example 3
In example 1, the same procedure as in example 1 was carried out except that 25 parts by mass of the component (e 1) was changed to 10 parts by mass, to prepare a cationic curable composition of comparative example 3.
Comparative example 4
In example 1, the same procedure as in example 1 was followed except that the component (e 1) was changed to a polycaprolactone polyol (e' 1) having a 2-functional hydroxyl group and a molecular weight of 500 (manufactured by Daicel Co., ltd.; placel 205), and a cationic curable composition of comparative example 4 was obtained.
Comparative example 5
In example 1, the same procedure as in example 1 was conducted except that the component (e 1) was changed to a polycaprolactone polyol (e' 2) having a 3-functional hydroxyl group and a molecular weight of 2000 (manufactured by Daicel Co., ltd.; placel 320) to prepare a cationic curable composition of comparative example 5.
Comparative example 6
In example 1, the same procedure as in example 1 was carried out except that the component (d 1) was removed, to prepare a cationic curable composition of comparative example 6.
< photo-curing test >
0.01g of the cation curable composition was dropped onto a glass test piece having a width of 25mm, a length of 100mm and a thickness of 5 mm. Then, the cumulative light amount was 3000mJ/cm by irradiation with AN ultraviolet irradiation device (manufactured by Jatec Co., ltd.; model: JUL-M-433AN-05, ultraviolet wavelength: 365 nm) 2 The active energy rays of (2) were measured to obtain a test piece. Next, a glass rod with a sharp tip was brought into contact with the test piece, and the curability of the cationically curable composition was evaluated according to the following criteria. In the following criteria, the curability was considered to be good if the ratio was equal to o.
[ evaluation criterion ]
O: no attachment on the rod
X: the stick is provided with attachments.
< test of Low temperature curability >
After dropping 0.1g of each of the cationically curable compositions onto a hot plate set at 100℃for 30 minutes, a glass rod having a sharp tip was brought into contact with the cured product, and the curability of the compositions was evaluated according to the following criteria. In the following criteria, if the ratio is O, the low-temperature curability is considered to be good.
[ evaluation criterion ]
O: no attachment on the rod
X: the stick is provided with attachments.
< test of tensile shear bond Strength of aluminum die cast >)
The cation curable compositions of examples and comparative examples were applied to test pieces of aluminum die casting ADC12 having a width of 25mm, a length of 100mm, and a thickness of 1 mm. Then, another test piece made of aluminum die cast ADC12 was attached and fixed by a clip so that the surface of the exterior package was 25mmx10mm. Then, the resultant was cured in a hot air drying oven set at 120℃for 60 minutes to obtain a test piece. Then, using the test piece, according to JISK6850:1999, tensile shear bond strength (in MPa) was measured at 25℃using a universal tensile tester (50 mm/min. Tensile speed). The tensile shear bond strength is a value at maximum strength. In order to use the cationically curable composition of the invention as an adhesive for assembling electronic/electrical component modules, vehicle components, and the like, the tensile shear adhesive strength is preferably 5.0MPa or more (including 5.0 MPa).
< test of tensile shear adhesive Strength against polyphenylene sulfide (PPS) >)
The cationic curable compositions of examples and comparative examples were applied to PPS test pieces having a width of 25mm, a length of 100mm and a thickness of 1 mm. Then, another PPS test piece was attached and fixed with a clip so that the outer package surface was 25mmx10mm. Then, the resultant was cured in a hot air drying oven set at 120℃for 60 minutes to obtain a test piece. Then, using the test piece, according to JISK6850:1999, tensile shear bond strength (in MPa) was measured at 25℃using a universal tensile tester (50 mm/min. Tensile speed). The tensile shear bond strength is a value at maximum strength. In order to use the cationically curable composition of the invention as an adhesive for assembling electronic/electrical component modules, vehicle components, and the like, the tensile shear adhesive strength is preferably 5.0MPa or more (including 5.0 MPa).
The test results are summarized in table 1 below. In table 1 below, "-" indicates that measurement was not performed.
TABLE 1
As is apparent from table 1, the cationic curable compositions of examples 1 to 3 are excellent in adhesion to aluminum die castings, PPS, and the like while maintaining photocurability and low-temperature curability.
Comparative example 1 shows that the composition of the present invention (A) was not a cationically curable composition, and that the composition was inferior in adhesion to PPS. In comparative example 2, the cation curable composition containing no component (E) of the present invention was found to have poor adhesion to aluminum die castings and PPS. In comparative example 3, the cation curable composition was not added in the predetermined range of the component (E) of the present invention, and it was found that the composition had poor adhesion to aluminum die cast parts and PPS. In comparative examples 4 and 5, the cation curable composition obtained by using the polyol which is not the component (E) of the present invention was found to have poor adhesion to aluminum die castings. Comparative example 6 shows that the cationic curable composition containing no component (D) of the present invention has poor low-temperature curability.
Industrial applicability
The cationically curable composition of the present invention is excellent in adhesion to aluminum die castings, PPS, and the like while maintaining photocurability and low-temperature curability, and therefore is suitable for a wide range of applications such as adhesion of module members for electric and electronic parts, and is industrially applicable.
The present application is based on japanese patent application No. 2019-223752, filed on date 11, 12 in 2019, the disclosure of which is incorporated herein by reference in its entirety.
Claims (12)
1. A cationically curable composition comprising the following components (A) to (E) and containing 10 to 95 parts by mass of the component (B) and 15 to 70 parts by mass of the component (E) relative to 100 parts by mass of the total amount of the components (A) and (B),
(A) The components are as follows: at least 1 selected from the group consisting of an aromatic bisphenol A type epoxy resin, an aromatic bisphenol F type epoxy resin, and an aromatic bisphenol E type epoxy resin,
(B) The components are as follows: at least one selected from the group consisting of (B1) and alicyclic epoxy resins (B2), wherein (B1) is at least one selected from the group consisting of hydrogenated bisphenol A epoxy resins, hydrogenated bisphenol F epoxy resins, hydrogenated bisphenol E epoxy resins, diglycidyl ethers of hydrogenated bisphenol A alkylene oxide adducts, diglycidyl ethers of hydrogenated bisphenol F alkylene oxide adducts, hydrogenated phenol novolac epoxy resins, and hydrogenated cresol novolac epoxy resins,
(C) The components are as follows: a photo-cationic polymerization initiator, which comprises a photo-cationic polymerization initiator,
(D) The components are as follows: a thermal cationic polymerization initiator,
(E) The components are as follows: polycaprolactone polyol having a hydroxyl group of 3 or more functions and a molecular weight of 1700 or less, where 3 or more functions comprise 3 functions, where 1700 or less comprise 1700.
2. The composition according to claim 1, wherein the component (B) is contained in an amount of 10 to 80 parts by mass based on 100 parts by mass of the total amount of the component (A) and the component (B).
3. The composition according to claim 1 or 2, wherein the component (D) is at least 1 selected from the group consisting of an aromatic sulfonium-based thermal cationic polymerization initiator, an aromatic iodonium-based thermal cationic polymerization initiator, and a thermal cationic polymerization initiator containing an amine salt.
4. The cationically curable composition according to claim 1 or 2 wherein the component (D) is a thermal cationic polymerization initiator comprising a salt having a quaternary ammonium cation.
5. The cationic curable composition according to claim 1 or 2, wherein the component (C) comprises at least one of an aromatic iodonium salt and an aromatic sulfonium salt.
6. The cationically curable composition according to claim 1 or 2 wherein (B2) is a 3, 4-epoxycyclohexylmethyl (3 ',4' -epoxycyclohexane carboxylate, epsilon-caprolactone-modified 3',4' -epoxycyclohexylmethyl, 3, 4-epoxycyclohexane carboxylate, bis (3, 4-epoxycyclohexyl) adipate, 1, 2-epoxy-4-vinylcyclohexane, 1, 4-cyclohexanedimethanol diglycidyl ether, epoxyethyldivinyl cyclohexane, bisepoxyvinyl cyclohexane, 1,2, 4-trioxyethylcyclohexane, limonene dioxide, alicyclic epoxy-containing siloxane oligomer.
7. The cationically curable composition according to claim 1 or 2, wherein the component (B) comprises only any one selected from the group consisting of the components (B1) and (B2).
8. The cationically curable composition according to claim 1 or 2, wherein the component (B) comprises the component (B1) and the component (B2).
9. The cationically curable composition according to claim 1 or 2 for use in adhesives.
10. The composition according to claim 1 or 2, which is used as an adhesive for the case where the adherend is an aluminum die-cast or PPS.
11. A cured product of the cationically curable composition according to any one of claims 1 to 10.
12. A bonded body obtained by bonding an adherend with the cationically curable composition according to any one of claims 1 to 10.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019223752 | 2019-12-11 | ||
| JP2019-223752 | 2019-12-11 | ||
| PCT/JP2020/041710 WO2021117396A1 (en) | 2019-12-11 | 2020-11-09 | Cationically curable composition, cured product, and joined body |
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| CN114761460A CN114761460A (en) | 2022-07-15 |
| CN114761460B true CN114761460B (en) | 2024-03-15 |
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- 2020-11-09 JP JP2021563798A patent/JPWO2021117396A1/ja active Pending
- 2020-11-09 TW TW109139050A patent/TW202122444A/en unknown
- 2020-11-09 WO PCT/JP2020/041710 patent/WO2021117396A1/en active Application Filing
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| CN114761460A (en) | 2022-07-15 |
| JPWO2021117396A1 (en) | 2021-06-17 |
| TW202122444A (en) | 2021-06-16 |
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