CN117693536A - Transparent resin composition - Google Patents
Transparent resin composition Download PDFInfo
- Publication number
- CN117693536A CN117693536A CN202280051371.5A CN202280051371A CN117693536A CN 117693536 A CN117693536 A CN 117693536A CN 202280051371 A CN202280051371 A CN 202280051371A CN 117693536 A CN117693536 A CN 117693536A
- Authority
- CN
- China
- Prior art keywords
- resin composition
- transparent resin
- component
- epoxy
- coupling agent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 129
- 239000003822 epoxy resin Substances 0.000 claims abstract description 76
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 76
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 42
- -1 acryl Chemical group 0.000 claims abstract description 27
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 19
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 18
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 9
- 229920005989 resin Polymers 0.000 claims description 23
- 239000011347 resin Substances 0.000 claims description 23
- 239000004593 Epoxy Substances 0.000 claims description 22
- 238000002834 transmittance Methods 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 10
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- 239000011521 glass Substances 0.000 abstract description 19
- 238000004383 yellowing Methods 0.000 abstract description 18
- 238000003860 storage Methods 0.000 abstract description 17
- 125000003700 epoxy group Chemical group 0.000 abstract description 11
- 239000010410 layer Substances 0.000 description 58
- 239000000047 product Substances 0.000 description 42
- 229920006287 phenoxy resin Polymers 0.000 description 29
- 239000013034 phenoxy resin Substances 0.000 description 29
- 239000000126 substance Substances 0.000 description 20
- 229930185605 Bisphenol Natural products 0.000 description 11
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 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 11
- 238000011156 evaluation Methods 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- 238000001035 drying Methods 0.000 description 10
- 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 description 10
- 238000000034 method Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 239000002131 composite material Substances 0.000 description 8
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 8
- 229920002799 BoPET Polymers 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 150000004714 phosphonium salts Chemical class 0.000 description 7
- 229920000139 polyethylene terephthalate Polymers 0.000 description 7
- 239000005020 polyethylene terephthalate Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000002966 varnish Substances 0.000 description 7
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 6
- 239000011888 foil Substances 0.000 description 6
- 239000011256 inorganic filler Substances 0.000 description 6
- 229910003475 inorganic filler Inorganic materials 0.000 description 6
- 239000004611 light stabiliser Substances 0.000 description 6
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- 239000006096 absorbing agent Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000002524 organometallic group Chemical group 0.000 description 4
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- UMPGNGRIGSEMTC-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UMPGNGRIGSEMTC-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 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 3
- 229940124543 ultraviolet light absorber Drugs 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 2
- OEBXWWBYZJNKRK-UHFFFAOYSA-N 1-methyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(C)CCCN21 OEBXWWBYZJNKRK-UHFFFAOYSA-N 0.000 description 2
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- GAYWTJPBIQKDRC-UHFFFAOYSA-N 8-trimethoxysilyloctyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCCCCCCOC(=O)C(C)=C GAYWTJPBIQKDRC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical class [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 2
- GGAUUQHSCNMCAU-UHFFFAOYSA-N butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)C(C(O)=O)CC(O)=O GGAUUQHSCNMCAU-UHFFFAOYSA-N 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- DEKLIKGLDMCMJG-UHFFFAOYSA-M decanoate;tetrabutylphosphanium Chemical compound CCCCCCCCCC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC DEKLIKGLDMCMJG-UHFFFAOYSA-M 0.000 description 2
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 239000013307 optical fiber Substances 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 239000011112 polyethylene naphthalate Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- RKLXSINPXIQKIB-UHFFFAOYSA-N trimethoxy(oct-7-enyl)silane Chemical compound CO[Si](OC)(OC)CCCCCCC=C RKLXSINPXIQKIB-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- KJYSXRBJOSZLEL-UHFFFAOYSA-N (2,4-ditert-butylphenyl) 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 KJYSXRBJOSZLEL-UHFFFAOYSA-N 0.000 description 1
- VVUWYXJTOLSMFV-UHFFFAOYSA-N (2-hydroxy-4-octylphenyl)-phenylmethanone Chemical compound OC1=CC(CCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 VVUWYXJTOLSMFV-UHFFFAOYSA-N 0.000 description 1
- ARVUDIQYNJVQIW-UHFFFAOYSA-N (4-dodecoxy-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 ARVUDIQYNJVQIW-UHFFFAOYSA-N 0.000 description 1
- AILUJKZWHGGGRF-UHFFFAOYSA-M (4-methylphenyl)-triphenylphosphanium;thiocyanate Chemical compound [S-]C#N.C1=CC(C)=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AILUJKZWHGGGRF-UHFFFAOYSA-M 0.000 description 1
- RUEBPOOTFCZRBC-UHFFFAOYSA-N (5-methyl-2-phenyl-1h-imidazol-4-yl)methanol Chemical compound OCC1=C(C)NC(C=2C=CC=CC=2)=N1 RUEBPOOTFCZRBC-UHFFFAOYSA-N 0.000 description 1
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 description 1
- ISNICOKBNZOJQG-UHFFFAOYSA-N 1,1,2,3,3-pentamethylguanidine Chemical compound CN=C(N(C)C)N(C)C ISNICOKBNZOJQG-UHFFFAOYSA-N 0.000 description 1
- NQOFYFRKWDXGJP-UHFFFAOYSA-N 1,1,2-trimethylguanidine Chemical compound CN=C(N)N(C)C NQOFYFRKWDXGJP-UHFFFAOYSA-N 0.000 description 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- SSUJUUNLZQVZMO-UHFFFAOYSA-N 1,2,3,4,8,9,10,10a-octahydropyrimido[1,2-a]azepine Chemical compound C1CCC=CN2CCCNC21 SSUJUUNLZQVZMO-UHFFFAOYSA-N 0.000 description 1
- LINDOXZENKYESA-UHFFFAOYSA-N 1,2-dimethylguanidine Chemical compound CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- XWFPIJRFFLYWRN-UHFFFAOYSA-N 1-(diaminomethylidene)-2-ethylguanidine Chemical compound CCN=C(N)N=C(N)N XWFPIJRFFLYWRN-UHFFFAOYSA-N 0.000 description 1
- JLPWQEHTPOFCPG-UHFFFAOYSA-N 1-(diaminomethylidene)-2-methylguanidine Chemical compound CN=C(N)N=C(N)N JLPWQEHTPOFCPG-UHFFFAOYSA-N 0.000 description 1
- MNWJUMZPXYLPGT-UHFFFAOYSA-N 1-(diaminomethylidene)-2-octadecylguanidine Chemical compound CCCCCCCCCCCCCCCCCCN=C(N)N=C(N)N MNWJUMZPXYLPGT-UHFFFAOYSA-N 0.000 description 1
- UBJPWXQSHUPNPG-UHFFFAOYSA-N 1-(diaminomethylidene)-2-prop-2-enylguanidine Chemical compound NC(N)=NC(N)=NCC=C UBJPWXQSHUPNPG-UHFFFAOYSA-N 0.000 description 1
- XZKLXPPYISZJCV-UHFFFAOYSA-N 1-benzyl-2-phenylimidazole Chemical compound C1=CN=C(C=2C=CC=CC=2)N1CC1=CC=CC=C1 XZKLXPPYISZJCV-UHFFFAOYSA-N 0.000 description 1
- PBODPHKDNYVCEJ-UHFFFAOYSA-M 1-benzyl-3-dodecyl-2-methylimidazol-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCN1C=C[N+](CC=2C=CC=CC=2)=C1C PBODPHKDNYVCEJ-UHFFFAOYSA-M 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 1
- RUFZNDNBXKOZQV-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrolo[1,2-a]benzimidazole Chemical compound C1=CC=C2N(CCC3)C3=NC2=C1 RUFZNDNBXKOZQV-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
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- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
- GHPYAGKTTCKKDF-UHFFFAOYSA-M tetraphenylphosphanium;thiocyanate Chemical compound [S-]C#N.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 GHPYAGKTTCKKDF-UHFFFAOYSA-M 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910052718 tin Chemical class 0.000 description 1
- 239000011135 tin Chemical class 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 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
- C08G59/20—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 epoxy compounds used
-
- 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
- C08G59/20—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 epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
-
- 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
- C08G59/20—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 epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
- C08G59/308—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5425—Silicon-containing compounds containing oxygen containing at least one C=C bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/52—Encapsulations
- H01L33/56—Materials, e.g. epoxy or silicone resin
Landscapes
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Power Engineering (AREA)
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Provided is a transparent resin composition which has excellent storage stability and can form a cured product having excellent yellowing resistance and adhesion strength to glass. A transparent resin composition comprising (A) an epoxy resin having a fluoroalkyl group and/or an alicyclic structure, (B) at least one selected from a (meth) acryl-containing silane coupling agent, an epoxy group-containing silane coupling agent and a vinyl group-containing silane coupling agent, and (C) a curing accelerator.
Description
Technical Field
The present invention relates to a transparent resin composition.
Background
The transparent resin composition is used as a sealing material, an adhesive material, or the like for transparent parts of electronic devices such as LED devices, transparent FPCs, and the like. As such a transparent resin composition, for example, patent document 1 discloses a resin composition containing bisphenol AF-type epoxy resin, thermoplastic resin, and curing accelerator.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open publication No. 2019-167428
Disclosure of Invention
Problems to be solved by the invention
The thermosetting resin composition described in patent document 1 may be cured slowly during storage, and the pot life is shortened, so that a resin composition having excellent storage stability is required. In addition, for use in transparent parts of electronic devices such as LED devices and transparent FPCs, a transparent resin composition capable of forming a cured product excellent in yellowing resistance is required. Further, a transparent resin composition capable of forming a cured product excellent in adhesion strength to glass used in transparent parts of electronic devices is demanded.
The present invention has been made in view of the above-described circumstances, and an object thereof is to provide a transparent resin composition which is excellent in storage stability and capable of forming a cured product excellent in yellowing resistance and adhesion strength to glass.
Means for solving the problems
The present invention capable of achieving the above object is as follows.
A transparent resin composition comprising the following components (A) to (C):
(A) An epoxy resin having a fluoroalkyl group and/or an alicyclic structure,
(B) At least one selected from the group consisting of a (meth) acryl-containing silane coupling agent, an epoxy-containing silane coupling agent and a vinyl-containing silane coupling agent, and
(C) A curing accelerator.
The transparent resin composition according to the above [1], wherein the content of the component (B) is 0.1 to 20% by mass relative to the nonvolatile component of the transparent resin composition.
The transparent resin composition according to the above [1] or [2], which further comprises a polymer compound.
The transparent resin composition according to any one of the above [1] to [3], wherein the transparent resin composition layer formed of the transparent resin composition has a thickness of 25 μm and has an average value of total light transmittance of 80% or more at a wavelength of 380 to 780 nm.
The transparent resin composition according to any one of the above [1] to [4], wherein the average value of the total light transmittance at a wavelength of 380 to 780nm of a cured product layer having a thickness of 25 μm formed from the transparent resin composition is 80% or more.
A resin sheet having a laminated structure comprising a support and a transparent resin composition layer formed from the transparent resin composition according to any one of the above [1] to [5 ].
The resin sheet according to the above [6], wherein the transparent resin composition layer has an average value of total light transmittance of 80% or more at a wavelength of 380 to 780 nm.
An electronic device comprising a cured layer formed from the transparent resin composition according to any one of the above [1] to [5 ].
The electronic device according to item [8], wherein an average value of total light transmittance of the cured product layer at a wavelength of 380 to 780nm is 80% or more.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, a transparent resin composition which has excellent storage stability and can form a cured product having excellent yellowing resistance and adhesion strength to glass can be obtained.
Detailed Description
The present invention provides a transparent resin composition comprising the following components (A) to (C):
(A) An epoxy resin having a fluoroalkyl group and/or an alicyclic structure,
(B) At least one selected from the group consisting of a (meth) acryl-containing silane coupling agent, an epoxy-containing silane coupling agent and a vinyl-containing silane coupling agent, and
(C) A curing accelerator.
In the present invention, unless otherwise specified, only 1 kind of each component may be used, or 2 or more kinds may be used in combination. The following will describe the components (A) to (C) in order.
Epoxy resin having fluoroalkyl group and/or alicyclic structure
The component (A) used in the present invention is an epoxy resin having a fluoroalkyl group and/or an alicyclic structure.
In the present specification, the term "epoxy resin" refers to a thermosetting resin having an epoxy group and having an epoxy equivalent weight of 5000g/eq or less. The epoxy equivalent herein refers to the gram number (unit: g/eq) of the resin containing 1 gram equivalent of epoxy group. In other words, the epoxy equivalent refers to a value obtained by dividing the molecular weight of the resin by the number of epoxy groups contained in the resin, that is, the molecular weight of an average of 1 epoxy group. The epoxy equivalent is measured according to the method specified in JIS K7236.
(A) The fluoroalkyl group that the component can have is preferably C from the viewpoint of yellowing resistance 1-6 Fluoroalkyl, more preferably C 1-6 Perfluoroalkyl groups, particularly preferably trifluoromethyl groups.
In the present specification, "C x-y "(x and y: integer) means that the number of carbon atoms is from x to y.
In the present specification, "fluoroalkyl" means an alkyl group substituted with a fluorine atom, and "perfluoroalkyl" means an alkyl group in which all hydrogen atoms are replaced with fluorine atoms.
In the present specification, the term "C 1-6 Examples of the fluoroalkyl group "include fluoromethyl group, difluoromethyl group, perfluoromethyl group (i.e., trifluoromethyl group), 2-fluoroethyl group, 2-trifluoroethyl group, perfluoroethyl group, 2-difluoropropyl group, perfluoropropyl group, perfluorobutyl group, perfluoropentyl group, and perfluorohexyl group.
In the present specification, the term "C 1-6 Examples of the perfluoroalkyl group include the above-mentioned "C 1-6 Perfluoroalkyl groups are examples of fluoroalkyl groups.
(A) The alicyclic structure that the component can have is preferably C from the viewpoint of yellowing resistance 3-12 Alicyclic structure. The alicyclic structure may be any of a monocyclic structure, a bicyclic structure, a condensed polycyclic structure, and a condensed polycyclic structure including a bicyclic ring. (A) The components canThe alicyclic structure may have 1 kind or 2 or more kinds. (A) The alicyclic structure that the component can have is more preferably C 3-8 A cycloalkane ring structure and/or a dicyclopentadiene ring structure. That is, the component (A) is more preferably a compound having a group selected from fluoroalkyl groups and C 3-8 An epoxy resin having at least one of a cycloalkane ring structure and a dicyclopentadiene ring structure. In the present specification, the term "C 3-8 Examples of the cycloalkane ring "include a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring and a cyclooctane ring.
(A) The alicyclic structure that the component can have is more preferably C 5-6 Cycloalkane ring structures (i.e., cycloheptane ring structures, cyclohexane ring structures).
Examples of the epoxy resin having a fluoroalkyl group include bisphenol AF-type epoxy resins having a trifluoromethyl group. The fluorine-containing epoxy resin described in WO2011/089947 can be used as an epoxy resin having a fluoroalkyl group. In the present specification, the term "X-type epoxy resin" (X, bisphenol AF) refers to an epoxy resin having a structure derived from X, as is known in the art of epoxy resins.
Examples of the epoxy resin having an alicyclic structure include bisphenol TMC-type epoxy resin having a cyclohexane ring structure and bisphenol Z-type epoxy resin having a cyclohexane ring structure. In addition, an epoxy resin having a cyclohexane ring structure (for example, "EHPE3150" manufactured by the dygroup company) other than bisphenol TMC type epoxy resin and bisphenol Z type epoxy resin may be used as the component (a).
(A) From the viewpoint of yellowing resistance of the component(s),
(i) Preferably an epoxy resin having a fluoroalkyl group and/or an epoxy resin having an alicyclic structure,
(ii) More preferably selected from the group consisting of having C 1-6 Fluoroalkyl epoxy resin, having C 3-8 At least one of an epoxy resin having a cycloalkane ring structure and an epoxy resin having a dicyclopentadiene ring structure,
(iii) Even more preferably having C 1-6 Perfluoroalkyl-containing epoxy resins and/or C-containing epoxy resins 5-6 Epoxy tree of cycloparaffin ring structureThe fat of the product is used for preparing the product,
(iv) Further preferred are epoxy resins having trifluoromethyl groups and/or epoxy resins having cyclohexane ring structures,
(v) Bisphenol AF type epoxy resin and/or epoxy resin having a cyclohexane ring structure are particularly preferable.
(A) The components may be commercially available ones, or may be ones produced by a known method (for example, reaction of bisphenol AF, bisphenol TMC or bisphenol Z with epichlorohydrin). Examples of the commercial products include Mitsubishi chemical products "YX7760", "YX8000", "YX8034", manufactured by Mitsubishi, as well as "EHPE3150", "EHPE3150CE", "Faseyi 2021P", "Meshi real world, as well as" Faseyi land 2081P "," Faseyi real world 2000"," Faseyi real world, as well as "Faseyi land 8000", manufactured by DIC, as well as "HP-7200", "HP-7200L", "HP-7200H", manufactured by Japanese chemical products, as well as "XD-1000", manufactured by Koseyi chemical products, as well as "Jiseyi super コ", manufactured by Zhou and electrical products, "Hemakida, as well as" THI-DE "," CDMDG ", manufactured by Ems, as" MEDE-102 "," DE-103"," DE-DDE "manufactured by Mitsubishi", as well as "manufactured by Nitsubishi chemical products" DE "," DE-DDE "manufactured by Nitsuki".
(A) The epoxy equivalent of the component (a) is preferably 50 to 5,000g/eq, more preferably 80 to 2,000g/eq, still more preferably 100 to 1,500g/eq, from the viewpoint of adhesion strength of the cured product of the transparent resin composition.
The content of the component (a) is preferably 20 to 94% by mass, more preferably 40 to 89% by mass, and even more preferably 50 to 84% by mass, relative to the nonvolatile component of the transparent resin composition, from the viewpoint of yellowing resistance. When a plurality of components (a) are used, the content thereof means the total content of the plurality of components (a). When a plurality of components other than the component (a) are used, the content thereof also means the total content of the components.
(B) at least one selected from the group consisting of (meth) acryl-containing silane coupling agent, epoxy-containing silane coupling agent and vinyl-containing silane coupling agent
The component (B) used in the present invention is at least one selected from the group consisting of a (meth) acryl-containing silane coupling agent, an epoxy-containing silane coupling agent and a vinyl-containing silane coupling agent.
(A) The components have excellent yellowing resistance. In addition, by using the component (B), the adhesion strength of the cured product to glass can be improved while maintaining excellent yellowing resistance of the cured product obtained from the resin composition containing the component (a). Further, the cured product obtained from the resin composition containing the component (a) tends to have a reduced fracture toughness, but the use of the component (B) can improve the fracture toughness of the cured product.
Examples of the (meth) acryl-containing silane coupling agent include 3-acryloxypropyl trimethoxysilane, 3-methacryloxypropyl methyl dimethoxy silane, 3-methacryloxypropyl trimethoxysilane, 3-methacryloxypropyl methyl diethoxy silane, 3-methacryloxypropyl triethoxy silane, and 8-methacryloxyoctyl trimethoxysilane.
Examples of the epoxy group-containing silane coupling agent include 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, 3-epoxypropoxypropylmethyldimethoxysilane, 3-epoxypropoxypropyltrimethoxysilane, 3-epoxypropoxypropylmethyldiethoxysilane, 3-epoxypropoxypropyltriethoxysilane, and 8-epoxypropoxyoctyltrimethoxysilane.
Examples of the vinyl-containing silane coupling agent include vinyltrimethoxysilane, vinyltriethoxysilane, and 7-octenyltrimethoxysilane.
(B) The components may be commercially available ones. Examples of such commercial products include "KBM-5103", "KBM-502", "KBM-503", "KBE-502", "KBE-503", "KBM-5803", "KBM-303", "KBM-402", "KBM-403", "KBE-402", "KBE-403", "KBM-4803", "KBM-1003", "KBM-1083" manufactured by Xin Yue chemical industries, ltd.
From the viewpoint of the adhesion strength of the cured product, the component (B) is preferably at least one selected from the group consisting of 3-acryloxypropyl trimethoxysilane, 3-methacryloxypropyl methyl dimethoxy silane, 3-methacryloxypropyl trimethoxysilane, 8-methacryloxyoctyl trimethoxysilane, 2- (3, 4-epoxycyclohexyl) ethyl trimethoxysilane, 3-epoxypropoxy propyl methyl dimethoxy silane, 3-epoxypropoxy propyl trimethoxysilane, 8-epoxypropoxy octyl trimethoxysilane, vinyl trimethoxysilane, and 7-octenyl trimethoxysilane.
In order to suppress the occurrence of warpage due to shrinkage upon curing of the transparent resin composition, component (B)
(i) Preferably a (meth) acryl-containing silane coupling agent,
(ii) More preferably an acryl-containing silane coupling agent.
The content of the component (B) is preferably 0.1 to 20% by mass, more preferably 0.75 to 15% by mass, and even more preferably 1.0 to 10% by mass, relative to the nonvolatile component of the transparent resin composition, from the viewpoint of the adhesion strength of the cured product.
Depending on the kind of the silane coupling agent used (e.g., mercapto group-containing silane coupling agent), the storage stability of the transparent resin composition may be lowered. However, in the present invention, as the component (B), at least one selected from the group consisting of a (meth) acryl-containing silane coupling agent, an epoxy group-containing silane coupling agent and a vinyl group-containing silane coupling agent is used, whereby storage stability can be improved.
From the viewpoint of storage stability, the transparent resin composition of the present invention preferably does not contain a silane coupling agent other than the component (B) (hereinafter, sometimes referred to as "other silane coupling agent") or contains other silane coupling agent in an amount of 25 mass% or less relative to the total of other silane coupling agent and the component (B) (i.e., the content of other silane coupling agent is limited to 25 mass% or less relative to the total of other silane coupling agent and the component (B)). The content of the other silane coupling agent is preferably 15 mass% or less, more preferably 10 mass% or less, based on the total of the other silane coupling agent and the component (B).
(C) curing accelerator
The component (C) used in the present invention is a curing accelerator. In the present specification, the "curing accelerator" means an additive that accelerates the curing reaction of the (a) components (i.e., the epoxy resin having a fluoroalkyl group and/or an alicyclic structure) with each other. In the epoxy field, an additive that promotes the curing reaction of epoxy resins with each other is sometimes referred to as a curing agent (in particular, a catalyst-type curing agent).
Examples of the curing accelerator as the component (C) include phosphorus-based curing accelerators (for example, phosphonium salts and phosphines), imidazole-based curing accelerators, amine-based curing accelerators, guanidine-based curing accelerators and metal-based curing accelerators.
Examples of phosphonium salts include phosphonium borate compounds, tetraphenylphosphonium tetraphenylborate, n-butylphosphonium tetraphenylborate, tetrabutylphosphonium decanoate, (4-methylphenyl) triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, and butyltriphenylphosphonium thiocyanate. As the phosphonium salt, commercially available ones can be used. As such a commercial product, for example, "TBP-DA" manufactured by North Korea chemical Co., ltd.
Examples of the phosphine include triphenylphosphine, tricyclohexylphosphine, tributylphosphine, and methyldiphenylphosphine.
As the imidazole-based curing accelerator, there is used, examples thereof include 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1, 2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, and 1-cyanoethyl-2-undecylimidazolium trimellitate, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2, 4-diamino-6- [2' -methylimidazolyl- (1 ') ] -ethyl-s-triazine, 2, 4-diamino-6- [2' -undecylimidazolyl- (1 ') ] -ethyl-s-triazine, 2, 4-diamino-6- [2' -ethyl-4 ' -methylimidazolyl- (1 ') ] -ethyl-s-triazine, 2, 4-diamino-6- [2' -methylimidazolyl- (1 ') ] -ethyl-s-triazine isocyanurate, and, 2-phenylimidazole isocyanuric acid adduct, imidazole compounds such as 2-phenyl-4, 5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2, 3-dihydro-1H-pyrrolo [1,2-a ] benzimidazole, 1-dodecyl-2-methyl-3-phenylmethylimidazolium chloride, 2-methylimidazoline, 2-phenylimidazoline and adducts of imidazole compounds with epoxy resins. As the imidazole-based curing accelerator, commercially available ones can be used. Examples of such commercial products include "P200-H50" manufactured by Mitsubishi chemical company and "1B2PZ-10M" manufactured by four-country chemical industry company.
Examples of the amine-based curing accelerator include trialkylamines such as triethylamine and tributylamine, 4-dimethylaminopyridine, benzyldimethylamine, 2,4, 6-tris (dimethylaminomethyl) phenol, and 1, 8-diazabicyclo (5, 4, 0) -undecene.
Examples of the guanidine-based curing accelerator include dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1- (o-tolylguanidine), dimethylguanidine, diphenylguanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5, 7-triazabicyclo [4.4.0] dec-5-ene, 7-methyl-1, 5, 7-triazabicyclo [4.4.0] dec-5-ene, 1-methylbiguanide, 1-ethylbiguanide, 1-n-butylbiguanide, 1-n-octadecylbiguanide, 1-dimethylbiguanide, 1-diethylbiguanide, 1-cyclohexylbiguanide, 1-allylbiguanide, 1-phenylbiguanide, and 1- (o-tolylguanide).
Examples of the metal-based curing accelerator include organometallic complexes or organometallic salts of cobalt, copper, zinc, iron, nickel, manganese, or tin. Examples of the organometallic complex include an organocobalt complex such as cobalt (II) acetylacetonate, cobalt (III) acetylacetonate, an organocopper complex such as copper (II) acetylacetonate, an organozinc complex such as zinc (II) acetylacetonate, an organoiron complex such as iron (III) acetylacetonate, an organonickel complex such as nickel (II) acetylacetonate, and an organomanganese complex such as manganese (II) acetylacetonate. Examples of the organometallic salts include zinc octoate, tin octoate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate.
The content of the component (C) is preferably 0.1 to 5% by mass, more preferably 0.3 to 4% by mass, and even more preferably 0.5 to 3% by mass, relative to the nonvolatile component of the transparent resin composition, from the viewpoint of storage stability.
From the viewpoint of yellowing resistance, phosphonium salts are preferably used as the curing accelerator. The content of the phosphonium salt in the transparent resin composition of the present invention is preferably 90 to 100% by mass, more preferably 95 to 100% by mass, based on the entire component (C). From the viewpoint of yellowing resistance, it is most preferable that the component (C) is a phosphonium salt, that is, the whole of the component (C) is composed of a phosphonium salt.
< other Components >)
The transparent resin composition of the present invention may contain components other than the components (a) to (C) (hereinafter, sometimes referred to as "other components") within a range that does not inhibit the effects of the present invention. Examples of the other components include a polymer compound, an epoxy resin other than the component (a), an organic solvent, an antioxidant, an ultraviolet absorber, and a light stabilizer. The other components may be used in an amount of 1 or 2 or more. The other components are described in order below.
(Polymer compound)
In order to form a film of the transparent resin composition, a polymer compound (sometimes referred to as "(D) component" in the present specification) is preferably used. In the present specification, the "polymer compound" refers to a compound having a weight average molecular weight (hereinafter, sometimes referred to as "Mw") of 1,000 or more. The Mw may be determined by Gel Permeation Chromatography (GPC).
Examples of the polymer compound as the component (D) include phenoxy resins, polyester polyols, polyether polyols, polycarbonate polyols, and (meth) acrylic resins. The preferred Mw for the phenoxy resin is as described below. The Mw of the polyester polyol is preferably 1,000 to 10,000. The Mw of the polyether polyol is 1,000 to 10,000. The Mw of the polycarbonate polyol is 1,000 to 10,000. The Mw of the (meth) acrylic resin is preferably 1,000 ～ 500,000.
(D) The component is preferably a phenoxy resin. In the present specification, "phenoxy resin" means a polyhydroxy polyether having a high molecular weight derived from bisphenol type structure. Examples of the phenoxy resin include a substance obtained by a reaction between bisphenol and epichlorohydrin and a substance obtained by a reaction between bisphenol type epoxy resin. The "bisphenol type epoxy resin" herein refers to an epoxy resin having a structure derived from bisphenols (e.g., bisphenol AF). The phenoxy resin may have a structure other than a structure derived from bisphenols.
The phenoxy resin may or may not have an epoxy group. In the present invention, "phenoxy resin having an epoxy group" and "epoxy resin" are distinguished by an epoxy equivalent. That is, in the present invention, a substance having an epoxy equivalent of more than 5000g/eq is classified as "phenoxy resin having an epoxy group", and a substance having an epoxy equivalent of 5000g/eq or less is classified as "epoxy resin". The epoxy equivalent of the phenoxy resin having an epoxy group is preferably more than 5,000g/eq and 40,000g/eq or less, more preferably 7,000 to 35,000g/eq, still more preferably 8,000 to 30,000g/eq, from the viewpoints of film formation of the transparent resin composition and adhesion strength of the cured product.
The weight average molecular weight of the phenoxy resin is preferably more than 10,000 and 100,000 or less, more preferably 20,000 ～ 80,000, and still more preferably 25,000 ～ 60,000, from the viewpoints of compatibility in the transparent resin composition and adhesion strength of the cured product.
The phenoxy resin may be commercially available, or may be produced by a known method (for example, a reaction between bisphenol and epichlorohydrin). Examples of the commercial products include Mitsubishi chemical and chemical agents "YX7200B35", "1256", "4250", "YX8100", "YX6954BH30", "YX7553BH30", "YL7769BH30", "YX7876B40", "YL9008B40", "YL6794", "YL7213", "YL7891BH30", "YL7482", and "YP-50", "YP-70S", "FX-293", "FX280S" manufactured by Mitsubishi chemical and chemical industries, respectively.
The phenoxy resin is from the viewpoint of yellowing resistance,
(i) Preferably a phenoxy resin having a fluoroalkyl group and/or a phenoxy resin having an alicyclic structure,
(ii) More preferably having C 1-6 Phenoxy tree of fluoroalkyl groupFat and/or have C 3-8 A phenoxy resin with a cycloparaffin ring structure,
(iii) Even more preferably having C 1-6 Phenoxy resins with perfluoroalkyl groups and/or having C 5-6 A phenoxy resin with a cycloparaffin ring structure,
(iv) Further preferred are phenoxy resins having trifluoromethyl groups and/or phenoxy resins having cyclohexane ring structures,
(v) Particularly preferred are bisphenol AF type phenoxy resin and/or phenoxy resin having cyclohexane ring structure,
(vi) Most preferred is bisphenol AF type phenoxy resin or phenoxy resin having cyclohexane ring structure.
In the present specification, the term "bisphenol AF type phenoxy resin" refers to a phenoxy resin having a structure derived from bisphenol AF.
In the case of using the component (D), the content thereof is preferably 10 to 50% by mass, more preferably 15 to 45% by mass, and even more preferably 20 to 40% by mass, relative to the nonvolatile component of the transparent resin composition, from the viewpoints of film formation of the transparent resin composition and adhesion strength of the cured product.
When the phenoxy resin is used as the component (D), the content of the phenoxy resin is preferably 5 to 50% by mass, more preferably 10 to 45% by mass, and even more preferably 15 to 40% by mass, relative to the nonvolatile component of the transparent resin composition, from the viewpoints of film formation of the transparent resin composition and adhesion strength of the cured product.
(epoxy resin other than the component (A))
The transparent resin composition of the present invention may contain an epoxy resin other than the component (a) (hereinafter, sometimes referred to as "other epoxy resin") within a range that does not hinder the effects of the present invention. The other epoxy resins may be used in an amount of 1 or 2 or more.
The other epoxy resin is not particularly limited, and a known epoxy resin can be used. Examples of the other epoxy resin include bisphenol a type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, biphenyl alkyl type epoxy resin, naphthol type epoxy resin, and naphthalene type epoxy resin. As the other epoxy resin, a mixture of a plurality of types of epoxy resins (for example, a mixture of bisphenol a type epoxy resin and bisphenol F type epoxy resin) may be used.
The epoxy equivalent of the other epoxy resin is preferably 50 to 5,000g/eq, more preferably 80 to 2,000g/eq, and still more preferably 100 to 1,500g/eq, from the viewpoint of adhesion strength of the cured product of the transparent resin composition.
From the viewpoint of yellowing resistance, the transparent resin composition of the present invention preferably contains no other epoxy resin or contains other epoxy resin in an amount of 50 mass% or less relative to the total of other epoxy resin and component (a) (i.e., the content of other epoxy resin is limited to 50 mass% or less relative to the total of other epoxy resin and component (a)). The content of the other epoxy resin is more preferably 30 mass% or less, and still more preferably 20 mass% or less, based on the total of the other epoxy resin and the component (a).
(organic solvent)
The transparent resin composition of the present invention may contain an organic solvent. That is, the transparent resin composition of the present invention may be a varnish-like transparent resin composition containing an organic solvent.
Examples of the organic solvent include ketones such as acetone, methyl Ethyl Ketone (MEK), cyclohexanone, ethyl acetate, butyl acetate, cellosolve acetate, acetate such as propylene glycol monomethyl ether acetate and carbitol acetate, cellosolves such as cellosolve, carbitol such as butyl carbitol, aromatic hydrocarbons such as toluene and xylene, dimethylformamide, dimethylacetamide and N-methylpyrrolidone.
When the organic solvent is used, the content thereof is preferably 5 to 50% by mass, more preferably 10 to 45% by mass, and even more preferably 15 to 40% by mass, relative to the entire transparent resin composition.
(antioxidant)
Examples of the antioxidant include hindered phenol antioxidants, phosphorus antioxidants, and sulfur antioxidants. Specific examples of the antioxidant include dibutylhydroxytoluene (BHT), pentaerythritol tetrakis (3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate) (IRGANOX 1010, manufactured by BASF), 2-thiodiethylenebis [3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate ] (IRGANOX 1035, manufactured by BASF), and 1,3, 5-tris [ [3, 5-bis (1, 1-dimethylethyl) -4-hydroxyphenyl ] methyl ] -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione (IRGANOX 3114, manufactured by BASF).
(ultraviolet absorber)
Examples of the ultraviolet absorber include benzophenone ultraviolet absorbers, benzotriazole ultraviolet absorbers, salicylic acid ultraviolet absorbers, triazine ultraviolet absorbers, and cyanoacrylate ultraviolet absorbers.
Examples of the benzophenone-based ultraviolet light absorber include 2-hydroxy-4-octoxybenzophenone, 2, 4-dihydroxy-benzophenone, 2-hydroxy-4-methoxy-benzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, 2-hydroxy-4-n-octyl-benzophenone, 2-hydroxy-4-n-dodecoxy-benzophenone, bis (5-benzoyl-4-hydroxy-2-methoxyphenyl) methane, 2' -dihydroxy-4-methoxy-benzophenone, and 2,2' -dihydroxy-4, 4' -dimethoxybenzophenone.
Examples of the benzotriazole-based ultraviolet light absorber include 2- (2 ' -hydroxy-5 ' -methylphenyl) benzotriazole, 2- [2' -hydroxy-3 ',5' -bis (α, α -dimethylbenzyl) phenyl ] -benzotriazole, 2- (2 ' -hydroxy-3 ',5' -di-t-butylphenyl) -benzotriazole, 2- (2 ' -hydroxy-3 ' -t-butyl-5 ' -methylphenyl) -5-chlorobenzotriazole, 2- (2 ' -hydroxy-3 ',5' -di-t-butylphenyl) -5-chlorobenzotriazole, 2- (2 ' -hydroxy-3 ',5' -di-t-amyl) benzotriazole, 2- (2 ' -hydroxy-5 ' -t-octylphenyl) benzotriazole, and 2, 2-methylenebis [4- (1, 3-tetramethylbutyl) -6- (2N-benzotriazole-2-yl) phenol ].
Examples of the salicylic acid-based ultraviolet absorber include phenyl salicylate, 4-t-butylphenyl 2-hydroxybenzoate, phenyl 2-hydroxybenzoate, 2, 4-di-t-butylphenyl 3, 5-di-t-butyl-4-hydroxybenzoate, hexadecyl 3, 5-di-t-butyl-4-hydroxybenzoate, and ethyl 2-cyano-3, 3-diphenylacrylate.
Examples of the triazine ultraviolet light absorber include 2- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) -5-hexyloxyphenol, 2- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) -5- [2- (2-ethylhexanoyloxy) ethoxy ] phenol, 2- [4, 6-bis (dimethylphenyl) -1,3, 5-triazin-2-yl ] -5- {3- [ (2-ethylhexyl) oxy ] -2-hydroxypropoxy } -phenol, and 2,4, 6-tris (2-hydroxy-4-hexyloxy-3-methylphenyl) -1,3, 5-triazine.
The ultraviolet absorber may be commercially available ones. Examples of such commercial products include "Chimassorb 81FL", "Tinuvin P", "Tinuvin213", "Tinuvin234", "Tinuvin 326", "Tinuvin 360", "Tinuvin 571", "Tinuvin 1577ED", "Tinuvin 120", and "EVERSORB 11", "EVERSORB 12", "EVERSORB 40", "EVERSORB 71", "EVERSORB 73", "EVERSORB 78", "EVERSORB 80", "EVERSORB 109", and "5405" manufactured by the nanking company, and "ADEKA" manufactured by ADEKA company, such as "Tinuvin 1577ED", "Tinuvin 120", and "EVERSORB 11", "EVERSORB 12", "EVERSORB 40", "EVERSORB 71", "EVERSORB 73", "evekerb 78", and "ales corporation".
(light stabilizer)
Examples of the light stabilizer include hindered amine light stabilizers.
As the hindered amine-based light stabilizer, examples thereof include bis (2, 6-tetramethyl-4-piperidinyl) sebacate, bis (1, 2, 6-pentamethyl-4-piperidinyl) -2-butyl-2- (4-hydroxy-3, 5-di-t-butylbenzyl) malonate, and butane-1, 2,3, 4-tetracarboxylic acid tetrakis (1, 2, 6-pentamethyl-4-piperidinyl) ester butane-1, 2,3, 4-tetracarboxylic acid tetra (1, 2, 6) -pentamethyl-4-piperidinyl) ester.
The light stabilizer may be commercially available ones. Examples of such commercial products include "Tinuvin 770DF" by BASF, tinuvin PA 144, and "ADEKA" by ADEKA, respectively, such as "Koujin LA-52", "Koujin LA-57", "Koujin LA-63P", "Koujin LA-68", "Koujin-La-72", "Koujin-LA-81", "Koujin-LA-87", and "Koujin-LA-87", respectively.
< inorganic filler >)
The transparent resin composition of the present invention may contain an inorganic filler in a range where transparency is maintained. From the viewpoint of transparency, the transparent resin composition of the present invention preferably contains no inorganic filler or an inorganic filler in an amount of 30 mass% or less relative to the nonvolatile component of the transparent resin composition (i.e., the content of the inorganic filler is limited to 30 mass% or less relative to the nonvolatile component of the transparent resin composition). The content of the inorganic filler is more preferably 20% by mass or less, still more preferably 10% by mass or less, and particularly preferably 5% by mass or less, relative to the nonvolatile component of the transparent resin composition.
< average value of total light transmittance of transparent resin composition layer having a thickness of 25 μm and a wavelength of 380 to 780nm >
The transparent resin composition layer of the present invention, which is formed from the transparent resin composition, has a thickness of 25. Mu.m, and the average value of the total light transmittance at a wavelength of 380 to 780nm is preferably 80% or more, more preferably 85% or more, and still more preferably 90% or more. The average value can be measured by the method described in the examples section described later.
< average value of total light transmittance of a cured product layer having a thickness of 25 μm and a wavelength of 380 to 780nm >
The average value of the total light transmittance of the cured product layer having a thickness of 25 μm and a wavelength of 380 to 780nm formed from the transparent resin composition of the present invention is preferably 80% or more, more preferably 85% or more, and still more preferably 90% or more. The average value can be measured by the method described in the examples section described later.
< resin sheet >)
The present invention also provides a resin sheet having a laminated structure comprising a support and a transparent resin composition layer formed of the transparent resin composition of the present invention. In the present invention, a protective film may be used. That is, the resin sheet of the present invention may have a laminated structure including a support, a transparent resin composition layer, and a protective film in this order. Other layers (e.g., release layer, adhesive layer) may be present between the support and the transparent resin composition layer, and between the transparent resin composition layer and the protective film.
The thickness of the transparent resin composition layer is not particularly limited, but is preferably 1 μm or more, more preferably 1.5 μm or more, further preferably 2 μm or more, particularly preferably 5 μm or more, preferably 150 μm or less, preferably 120 μm or less, further preferably 100 μm or less, further preferably 80 μm or less.
Examples of the support include plastic films such as polyethylene, polypropylene, polyvinyl chloride, cycloolefin polymer, polyethylene terephthalate (hereinafter, may be abbreviated as "PET"), polyethylene naphthalate, polycarbonate, and polyimide, and metal foils such as aluminum foil, stainless steel foil, and copper foil. Among them, polyethylene terephthalate and polyethylene naphthalate are preferable, and inexpensive polyethylene terephthalate is particularly preferable. The support may have a release layer on the surface to be joined to the transparent resin composition layer. Examples of the release agent for forming the release layer include silicone-based release agents, alkyd-based release agents, and fluororesin-based release agents. The support may be subjected to a matte treatment, a corona treatment, or an antistatic treatment on the surface to be joined to the transparent resin composition layer.
The thickness of the support is not particularly limited, but is preferably 5 to 75. Mu.m, more preferably 10 to 60. Mu.m. In the case of using the support with a release layer, the thickness of the entire support with a release layer is preferably in the above range.
The resin sheet can be produced, for example, (1) by producing a clear resin composition in the form of a varnish, (2) by applying the clear resin composition to a support using a die coater or the like to form a coating film, and (3) by drying the obtained coating film to form a clear resin composition layer. The method for producing the clear resin composition in the form of a varnish is not particularly limited, and the clear resin composition can be produced by mixing the organic solvent and each component with a known machine such as a rotary mixer.
Drying of the coating film can be carried out by a known method such as heating or hot air blowing. The drying conditions are not particularly limited. The drying is preferably performed until the content of the organic solvent in the transparent resin composition layer becomes 10 mass% or less. The content of the organic solvent in the transparent resin composition layer after drying is more preferably 5 mass% or less. The drying time and the drying temperature also vary depending on the content of the organic solvent in the varnish-like transparent resin composition and the boiling point thereof, and the drying temperature is, for example, about 50 to 150 ℃, and the drying time is, for example, about 3 to 10 minutes.
The resin sheet may be stored in a roll form. In the case where the resin sheet has a protective film, the protective film may be peeled off, whereby the resin sheet is used.
The average value of the total light transmittance of the transparent resin composition layer of the resin sheet of the present invention at a wavelength of 380 to 780nm is preferably 80% or more, more preferably 85% or more, and still more preferably 90% or more, regardless of the thickness of the transparent resin composition layer. The average value can be measured by the method described in the examples section described later.
< electronic device >)
The present invention also provides an electronic device comprising a cured layer formed by the transparent resin composition of the present invention. Examples of the electronic device include an LED device and a transparent FPC.
The average value of the total light transmittance of the cured product layer of the electronic device of the present invention at a wavelength of 380 to 780nm is preferably 80% or more, more preferably 85% or more, and even more preferably 90% or more, regardless of the thickness of the cured product layer. The average value can be measured by the method described in the examples section described later.
The cured layer is preferably formed by heating the transparent resin composition layer. The heating method is not particularly limited, and the transparent resin composition layer may be heated by a known apparatus (for example, a hot air circulation oven, an infrared heater, a heating gun, or a high-frequency induction heating apparatus). The curing temperature is preferably 100℃or higher, more preferably 120℃or higher from the viewpoint of promoting the curing reaction, and is preferably 180℃or lower, more preferably 165℃or lower from the viewpoint of preventing coloration of the cured product layer. The curing time is preferably 10 minutes or more, more preferably 20 minutes or more, preferably 120 minutes or less, more preferably 90 minutes or less.
Examples
The present invention will be described more specifically with reference to the following examples, but the present invention is not limited to the following examples, and may be modified and implemented as appropriate within the scope of the gist described above and below, and all of them are included in the technical scope of the present invention. In the case where "parts" and "%" in the amounts of the components are not specifically described, they refer to "parts by mass" and "% by mass", respectively.
The components used in examples and comparative examples are shown below.
Component (A): epoxy resin having fluoroalkyl group and/or alicyclic structure
"YX7760" (bisphenol AF type epoxy resin, manufactured by Mitsubishi chemical company, epoxy equivalent: 245 g/eq)
"EHPE3150" (epoxy resin having cyclohexane ring structure, epoxy equivalent: 180g/eq, manufactured by the Seal company.)
< other epoxy resin >
"ZX-1059" (mixture of bisphenol A type epoxy resin (50%) and bisphenol F type epoxy resin (50%) manufactured by Nippon Kagaku Co., ltd., epoxy equivalent: 165 g/eq)
(B) at least one selected from the group consisting of (meth) acryl-containing silane coupling agent, epoxy-containing silane coupling agent and vinyl-containing silane coupling agent
"KBM-5103" (3-acryloxypropyl trimethoxysilane, manufactured by Xinyue chemical industry Co., ltd.)
"KBM-403" (3-glycidoxypropyl trimethoxysilane, from Xinyue chemical industries, ltd.)
"KBM-1003" (manufactured by Xinyue chemical industry Co., ltd., vinyl trimethoxysilane)
< other silane coupling agent >
"KBM-803" (3-mercaptopropyl trimethoxysilane, manufactured by Xinyue chemical industries, ltd.)
Component (C): curing accelerator >, of
"TBP-DA" (tetrabutylphosphonium decanoate, north America chemical Co., ltd.)
Component (D): polymer compound >
"YX7200B35" (solution of phenoxy resin having biphenyl structure and structure derived from bisphenol TMC, manufactured by Mitsubishi chemical company, organic solvent: methyl ethyl ketone, nonvolatile component: 35%, weight average molecular weight: 30,000, epoxy equivalent: 9,000 g/eq)
The clear resin compositions of examples and comparative examples were prepared according to the procedure shown below. In the following description, "parts" of the amount of each material used means "parts by mass" unless otherwise specified.
Example 1 >
23 parts of the solution "YX7200B35" of the component (D) ((D) component: 8.05 parts), (A) component "YX7760"18 parts and 1.4 parts of the component (B) component "KBM-5103" were mixed, and the resulting mixture was heated to dissolve the component (A) and the component (B). To this was mixed 0.36 parts of the component (C) 'TBP-DA', thereby preparing a clear resin composition in the form of a varnish.
Example 2 >
A varnish-like transparent resin composition was prepared in the same manner as in example 1, except that 18 parts of the component "EHPE3150" (alicyclic epoxy resin) was used instead of 18 parts of the component "YX 7760".
Example 3 >
(B) A varnish-like transparent resin composition was prepared in the same manner as in example 1, except that the amount of the component "KBM-5103" was changed from 1.4 parts to 3.0 parts.
Example 4 >
(B) A varnish-like transparent resin composition was prepared in the same manner as in example 1, except that the amount of the component "KBM-5103" was changed from 1.4 parts to 0.2 parts.
Example 5 >
A varnish-like transparent resin composition was prepared in the same manner as in example 1, except that 1.4 parts of component "KBM-403" as the component (B) was used in place of 1.4 parts of component "KBM-5103".
Example 6 >
A clear resin composition was prepared in the same manner as in example 1 except that 1.4 parts of component (B) 'KBM-1003' was used instead of 1.4 parts of component (B) 'KBM-5103'.
Example 7 >
A varnish-like transparent resin composition was prepared in the same manner as in example 1, except that the solution "YX7200B35" of component (D) was not used and the amount of component (B) 'KBM-5103' used was changed from 1.4 parts to 1.0 parts.
Comparative example 1 >
A clear resin composition in the form of a varnish was prepared in the same manner as in example 1, except that 1.4 parts of the component (B) 'KBM-5103' was not used.
Comparative example 2 >
A clear resin composition was prepared in the same manner as in example 1 except that 18 parts of the other epoxy resin "ZX-1059" was used instead of 18 parts of the component (A) 'YX 7760'.
Comparative example 3 >
A clear resin composition in the form of a varnish was prepared in the same manner as in example 1, except that 1.4 parts of the other silane coupling agent "KBM-803" was used in place of 1.4 parts of the component (B) 'KBM-5103'.
< measurement of average value of total light transmittance at wavelengths of 380 to 780nm and b)
(1) Preparation of sample for evaluation
The clear resin composition prepared in the examples or comparative examples was coated on a release layer of a PET film (NSH, thickness: 50 μm) treated with a non-silicone release agent by a die coater so that the thickness of the dried clear resin composition layer became 25 μm, and dried at 100℃for 5 minutes to form a clear resin composition layer, thereby obtaining a resin sheet having a laminate structure of "PET film/clear resin composition layer".
On the transparent resin composition layer of the obtained resin sheet, a glass slide (width: 76mm, depth: 26mm, thickness: 1.0mm, manufactured by Song Nitro industries Co., ltd.) was laminated using a vacuum laminator (V-160, manufactured by Yu コ, santa-matrix) to obtain a laminate having a laminate structure of "PET film/transparent resin composition layer/glass slide". The lamination was performed by reducing the pressure to 5hPa or less for 30 seconds and then pressing the slide glass at 80℃under a pressure of 0.3MPa for 30 seconds.
After heating the obtained laminate at 150℃for 30 minutes, the PET film was peeled off, and further heating at 150℃for 30 minutes, whereby the transparent resin composition layer was thermally cured, to obtain a laminate having a laminate structure of "cured layer (thickness: about 25 μm)/slide glass".
(2) Measurement of average value of total light transmittance at wavelengths of 380 to 780nm (hereinafter referred to as "average value of total light transmittance")
For the resin sheet having the laminate structure of "PET film/transparent resin composition layer" and the laminate having the laminate structure of "cured product layer/glass slide" obtained in the production of the sample for evaluation of "(1), a laminate having been assembled was usedThe total light transmittance was measured by using an optical fiber spectrophotometer (MCPD-7700 manufactured by Otsuka electronics Co., ltd.) which was an integrating sphere at a distance of 30mm from the sample. In the measurement of the resin sheet, a PET film used for the production of the resin sheet was used as a reference, and in the measurement of the laminate, a glass slide used for the production of the laminate was used as a reference, and an average value of total light transmittance of the transparent resin composition layer and the cured product layer was calculated as an index of transparency. The results are set forth in Table 1 below. Since the average value of the total light transmittance of the transparent resin composition layer and the cured product layer is the same, only one value is described in table 1 below.
(3) b measurement and evaluation of yellowing resistance
After the laminate obtained in "(1) preparation of sample for evaluation" was left to stand in an oven at 180 ℃ for 2 hours, the yellowing resistance was evaluated on the basis of the following criteria, using the above-mentioned optical fiber spectrophotometer, with the distance between the integrating sphere and the sample set to 30mm, the reference set to air, the viewing angle set to 2 degrees, and the color calculation under the light source D65 was performed. The results are set forth in Table 1 below.
(evaluation criterion for yellowing resistance)
Good (goodo): b is less than 1.0
Poor (×): b is 1.0 or more
< evaluation of adhesion Strength >)
The clear resin composition in the form of varnish prepared in the examples or comparative examples was coated on an aluminum foil having a composite film of an aluminum foil and a polyethylene terephthalate (PET) film (PET "AL 1N30", manufactured by eastern ocean aluminum vending corporation, eastern sea, thickness of the aluminum foil: 30 μm, thickness of the PET film: 25 μm) with a die coater so that the thickness of the layer of the clear resin composition after drying became 25 μm, and dried at 100 ℃ for 5 minutes to obtain a resin sheet having a laminated structure of "composite film/clear resin composition layer".
The obtained resin sheet was cut into a length of 100mm and a width of 20mm. Next, a glass slide (width: 76mm, depth: 26mm, and thickness: 1.0 mm) was laminated on the transparent resin composition layer of the cut laminate using a vacuum laminator (V-160, manufactured by cartridge コ), to obtain a laminate having a laminate structure of "composite film/transparent resin composition layer/glass slide". The lamination was performed by pressing the slide glass at 80℃and a pressure of 0.3MPa for 30 seconds after the air pressure was set to 5hPa or less for 30 seconds.
The obtained laminate was heated at 150 ℃ for 60 minutes, whereby the transparent resin composition layer was cured, resulting in a laminate having a laminate structure of "composite film/cured layer/slide glass". The obtained laminate was stored in a constant temperature and humidity tank set at a temperature of 85 ℃ and a humidity of 85% rh, and after 100 hours, the laminate was taken out to prepare an evaluation sample.
The obtained evaluation sample was set to a stretching speed of 60 mm/min in a direction of 90 degrees with respect to the longitudinal direction of the composite film, and the adhesion strength at the time of peeling the "composite film/cured product layer" from the slide glass at normal temperature was measured, and the adhesion strength was evaluated on the basis of the following criteria. The results are set forth in Table 1 below.
(evaluation criterion of seal Strength)
Good (goodo): the adhesion strength was 500gf/cm or more, or the composite film was broken when the adhesion strength was measured (hereinafter, referred to as "material breakage" in Table 1)
Poor (×): when the adhesion strength was less than 500gf/cm, or when the laminate having the laminate structure of "composite film/cured layer/slide glass" was taken out of the constant temperature and humidity tank, the cured layer was completely peeled off from the slide glass (hereinafter, referred to as "peeling" in Table 1)
< evaluation of storage stability >
The viscosities (initial viscosities) of the clear resin compositions in the form of varnishes immediately after the production of the examples and comparative examples were measured. Further, the viscosity (viscosity after storage) of the clear resin composition after storage at 23℃for 8 hours in a sealed state was measured. The storage stability was evaluated according to the following criteria based on the ratio of the viscosity after storage to the initial viscosity (viscosity after storage/initial viscosity). The results are set forth in Table 1 below.
(evaluation criterion of storage stability)
Good (good): the viscosity after preservation/initial viscosity is less than 1.5 times
Poor (×): the viscosity after preservation/initial viscosity is more than 1.5 times
When the viscosity of the clear varnish-like transparent resin composition is 0 mPa-sec or more and less than 500 mPa-sec, the viscosity is measured using "RE-85U" (E-type viscometer, 1 ° 24×r24 cone) manufactured by eastern machine industry company, and when the viscosity of the clear varnish-like transparent resin composition is 500 mPa-sec or more and 8000 mPa-sec or less, the viscosity is measured using "RE-80U" (E-type viscometer, 3 ° ×r9.7 cone) manufactured by eastern machine industry company.
TABLE 1
As shown in the results of table 1, in examples 1 to 7, cured products excellent in adhesion strength to glass can be formed as compared with comparative example 1 in which the component (B) was not used. In examples 1 to 7, a cured product having excellent yellowing resistance was formed as compared with comparative example 2 in which the component (a) was replaced with another epoxy resin. In examples 1 to 7, the transparent resin composition had better storage stability than comparative example 3 in which the component (B) was replaced with another silane coupling agent.
Industrial applicability
The transparent resin composition of the present invention is useful as, for example, a sealing material, an adhesive material, or the like for transparent parts of electronic devices such as LED devices and transparent FPCs.
The present application is based on Japanese patent application No. 2021-121880, filed at 26/7/2021, the contents of which are incorporated herein in their entirety.
Claims (9)
1. A transparent resin composition comprising the following components (A) to (C):
(A) An epoxy resin having a fluoroalkyl group and/or an alicyclic structure,
(B) At least one selected from the group consisting of a (meth) acryl-containing silane coupling agent, an epoxy-containing silane coupling agent and a vinyl-containing silane coupling agent, and
(C) A curing accelerator.
2. The transparent resin composition according to claim 1, wherein the content of the component (B) is 0.1 to 20% by mass relative to the nonvolatile component of the transparent resin composition.
3. The transparent resin composition according to claim 1 or 2, further comprising a high molecular compound.
4. The transparent resin composition according to claim 1, wherein the transparent resin composition layer having a thickness of 25 μm is formed from the transparent resin composition and has an average value of total light transmittance of 80% or more at a wavelength of 380 to 780 nm.
5. The transparent resin composition according to claim 1, wherein the average value of total light transmittance at a wavelength of 380 to 780nm of the cured product layer having a thickness of 25 μm formed from the transparent resin composition is 80% or more.
6. A resin sheet having a laminated structure comprising a support and a transparent resin composition layer formed by the transparent resin composition according to claim 1.
7. The resin sheet according to claim 6, wherein the transparent resin composition layer has an average value of total light transmittance of 380 to 780nm in wavelength of 80% or more.
8. An electronic device comprising a cured layer formed from the transparent resin composition of claim 1.
9. The electronic device according to claim 8, wherein an average value of total light transmittance of the cured product layer at a wavelength of 380 to 780nm is 80% or more.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021121881 | 2021-07-26 | ||
| JP2021-121881 | 2021-07-26 | ||
| PCT/JP2022/028561 WO2023008350A1 (en) | 2021-07-26 | 2022-07-25 | Transparent resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117693536A true CN117693536A (en) | 2024-03-12 |
Family
ID=85086909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202280051371.5A Pending CN117693536A (en) | 2021-07-26 | 2022-07-25 | Transparent resin composition |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPWO2023008350A1 (en) |
| KR (1) | KR20240036669A (en) |
| CN (1) | CN117693536A (en) |
| TW (1) | TW202319430A (en) |
| WO (1) | WO2023008350A1 (en) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0532866A (en) * | 1991-07-31 | 1993-02-09 | Shin Etsu Chem Co Ltd | Light-transmitting epoxy resin composition and photosemiconductor device |
| WO2015019512A1 (en) * | 2013-08-08 | 2015-02-12 | 日立化成株式会社 | Resin composition for optical waveguides, resin film for optical waveguides using same, optical waveguide and photoelectric composite wiring board |
| JP6606823B2 (en) * | 2014-12-03 | 2019-11-20 | 味の素株式会社 | Interlayer insulation resin composition, photosensitive film with support, printed wiring board, semiconductor device, and printed wiring board manufacturing method |
| JP2016180036A (en) * | 2015-03-23 | 2016-10-13 | 味の素株式会社 | Sealing resin composition and sealing sheet |
| WO2017183226A1 (en) * | 2016-04-18 | 2017-10-26 | Jnc株式会社 | Thermosetting resin composition, cured film, substrate provided with cured film, and electronic component |
| JP7071279B2 (en) * | 2016-11-18 | 2022-05-18 | リンテック株式会社 | Adhesive composition, encapsulation sheet, and encapsulant |
| JP6992635B2 (en) | 2018-03-22 | 2022-01-13 | 味の素株式会社 | Resin composition |
-
2022
- 2022-07-25 JP JP2023538502A patent/JPWO2023008350A1/ja active Pending
- 2022-07-25 WO PCT/JP2022/028561 patent/WO2023008350A1/en active Application Filing
- 2022-07-25 CN CN202280051371.5A patent/CN117693536A/en active Pending
- 2022-07-25 TW TW111127721A patent/TW202319430A/en unknown
- 2022-07-25 KR KR1020247006257A patent/KR20240036669A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2023008350A1 (en) | 2023-02-02 |
| TW202319430A (en) | 2023-05-16 |
| KR20240036669A (en) | 2024-03-20 |
| JPWO2023008350A1 (en) | 2023-02-02 |
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