JP7444068B2 - 硬化性樹脂組成物、硬化物及びシート状成形体 - Google Patents
硬化性樹脂組成物、硬化物及びシート状成形体 Download PDFInfo
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- JP7444068B2 JP7444068B2 JP2020553156A JP2020553156A JP7444068B2 JP 7444068 B2 JP7444068 B2 JP 7444068B2 JP 2020553156 A JP2020553156 A JP 2020553156A JP 2020553156 A JP2020553156 A JP 2020553156A JP 7444068 B2 JP7444068 B2 JP 7444068B2
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- epoxy resin
- polyether polyol
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- 239000011342 resin composition Substances 0.000 title claims description 65
- 239000003822 epoxy resin Substances 0.000 claims description 120
- 229920000647 polyepoxide Polymers 0.000 claims description 120
- 229920005989 resin Polymers 0.000 claims description 66
- 239000011347 resin Substances 0.000 claims description 66
- 229920005862 polyol Polymers 0.000 claims description 58
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 57
- 229920000570 polyether Polymers 0.000 claims description 57
- 150000003077 polyols Chemical class 0.000 claims description 57
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000002723 alicyclic group Chemical group 0.000 claims description 22
- 239000007787 solid Substances 0.000 claims description 20
- 239000004593 Epoxy Substances 0.000 claims description 19
- 230000001588 bifunctional effect Effects 0.000 claims description 11
- MEBONNVPKOBPEA-UHFFFAOYSA-N 1,1,2-trimethylcyclohexane Chemical group CC1CCCCC1(C)C MEBONNVPKOBPEA-UHFFFAOYSA-N 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 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 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000002430 hydrocarbons Chemical group 0.000 claims description 7
- 125000000962 organic group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000004848 polyfunctional curative Substances 0.000 claims 1
- 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 28
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000003795 chemical substances by application Substances 0.000 description 24
- 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 24
- -1 phenol compound Chemical class 0.000 description 23
- 239000002904 solvent Substances 0.000 description 22
- 229920003986 novolac Polymers 0.000 description 18
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
- 238000005452 bending Methods 0.000 description 14
- 125000003700 epoxy group Chemical group 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 12
- 150000002989 phenols Chemical class 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 8
- 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 7
- 239000003054 catalyst Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
- 150000002460 imidazoles Chemical class 0.000 description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000011256 inorganic filler Substances 0.000 description 4
- 229910003475 inorganic filler Inorganic materials 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229940079877 pyrogallol Drugs 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 239000012763 reinforcing filler Substances 0.000 description 3
- 239000012779 reinforcing material Substances 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
- XSTITJMSUGCZDH-UHFFFAOYSA-N 4-(4-hydroxy-2,6-dimethylphenyl)-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1C1=C(C)C=C(O)C=C1C XSTITJMSUGCZDH-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000004844 aliphatic epoxy resin Substances 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 description 2
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical group OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000002452 interceptive effect Effects 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000005453 ketone based solvent Substances 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
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- 238000000465 moulding Methods 0.000 description 2
- XOOMNEFVDUTJPP-UHFFFAOYSA-N naphthalene-1,3-diol Chemical compound C1=CC=CC2=CC(O)=CC(O)=C21 XOOMNEFVDUTJPP-UHFFFAOYSA-N 0.000 description 2
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 2
- OENHRRVNRZBNNS-UHFFFAOYSA-N naphthalene-1,8-diol Chemical compound C1=CC(O)=C2C(O)=CC=CC2=C1 OENHRRVNRZBNNS-UHFFFAOYSA-N 0.000 description 2
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- 239000002245 particle Substances 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 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
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- 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
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
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- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
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- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- NWOMMWVCNAOLOG-UHFFFAOYSA-N 1h-imidazol-5-ylmethanediol Chemical compound OC(O)C1=CN=CN1 NWOMMWVCNAOLOG-UHFFFAOYSA-N 0.000 description 1
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- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 description 1
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- KMRIWYPVRWEWRG-UHFFFAOYSA-N 2-(6-oxobenzo[c][2,1]benzoxaphosphinin-6-yl)benzene-1,4-diol Chemical compound OC1=CC=C(O)C(P2(=O)C3=CC=CC=C3C3=CC=CC=C3O2)=C1 KMRIWYPVRWEWRG-UHFFFAOYSA-N 0.000 description 1
- PULOARGYCVHSDH-UHFFFAOYSA-N 2-amino-3,4,5-tris(oxiran-2-ylmethyl)phenol Chemical compound C1OC1CC1=C(CC2OC2)C(N)=C(O)C=C1CC1CO1 PULOARGYCVHSDH-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
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- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- ZTXFOCMYRCGSMU-UHFFFAOYSA-M tetramethylphosphanium;bromide Chemical compound [Br-].C[P+](C)(C)C ZTXFOCMYRCGSMU-UHFFFAOYSA-M 0.000 description 1
- CRUVUWATNULHFA-UHFFFAOYSA-M tetramethylphosphanium;hydroxide Chemical compound [OH-].C[P+](C)(C)C CRUVUWATNULHFA-UHFFFAOYSA-M 0.000 description 1
- TVVPMLFGPYQGTG-UHFFFAOYSA-M tetramethylphosphanium;iodide Chemical compound [I-].C[P+](C)(C)C TVVPMLFGPYQGTG-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 230000007704 transition Effects 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
- NIUZJTWSUGSWJI-UHFFFAOYSA-M triethyl(methyl)azanium;chloride Chemical compound [Cl-].CC[N+](C)(CC)CC NIUZJTWSUGSWJI-UHFFFAOYSA-M 0.000 description 1
- MQAYPFVXSPHGJM-UHFFFAOYSA-M trimethyl(phenyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC=C1 MQAYPFVXSPHGJM-UHFFFAOYSA-M 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
- ADZJWYULTMTLQZ-UHFFFAOYSA-N tritylphosphane;hydrobromide Chemical compound [Br-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 ADZJWYULTMTLQZ-UHFFFAOYSA-N 0.000 description 1
- IZYFBZDLXRHRLF-UHFFFAOYSA-N tritylphosphane;hydroiodide Chemical compound [I-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 IZYFBZDLXRHRLF-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
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Description
近年、各種エレクトロデバイスは、軽量化・薄膜化や形状の自由度などが求められる用途があり、フレキシブル化が注目されている。エレクトロデバイスのフレキシブル化には、従来、基材として用いられていたガラスに代わり、プラスチックフィルムが用いられる。このプラスチックフィルムには、耐折り曲げ性に優れることが求められる。また、半導体材料を実装するためには半田リフロー工程に耐えうる耐熱性が必要になる。更にディスプレイの基材として使用するためには透明性も必要になる。
また、特許文献1に記載の硬化性樹脂組成物では、フォルダブルOLEDディスプレイのフィルムに要求される透明性、耐折り曲げ性(可撓性)及び耐熱性の全てをバランスよく満たすことができない。
「全エポキシ樹脂成分」とは、以下に示す本発明のポリエーテルポリオール樹脂及び3官能以上のエポキシ樹脂と後述するその他のエポキシ化合物との合計を意味する。
本発明のシート状成形体は、フィルム状成形体を包含する。
本発明の硬化性樹脂組成物は、下記一般式(1)で表され、エポキシ当量が7,000~100,000g/当量であるポリエーテルポリオール樹脂(以下、「本発明のポリエーテルポリオール樹脂」と称す場合がある。)と、3官能以上のエポキシ樹脂と、エポキシ樹脂硬化剤とを含むことを特徴とする。
本発明のポリエーテルポリオール樹脂は、前記一般式(1)で表されるものである。一般式(1)中のA1及びA2は、下記一般式(3)で表される基であることが耐熱性の観点から好ましい。
R1としては水素原子、炭素数1~2の炭化水素基又はハロゲン原子から選ばれる基が好ましい。
本発明において「エポキシ当量」とは、「1当量のエポキシ基を含むエポキシ樹脂の質量」と定義され、JIS K7236に準じて測定することができる。
反応条件等にもよるが、エポキシ基:フェノール水酸基=1:1未満の場合、末端がエポキシ基となり、エポキシ基:フェノール性水酸基=1:1より大の場合、末端がフェノール性水酸基になる確率が高くなる。
ケトン系溶媒の具体例としては、アセトン、メチルエチルケトン、メチルイソブチルケトン、2-ヘプタノン、4-ヘプタノン、2-オクタノン、シクロヘキサノン、アセチルアセトン、ジオキサンなどが挙げられる。
本発明のポリエーテルポリオール樹脂と共に用いるエポキシ樹脂は、3官能以上のエポキシ樹脂であり、例えば、フェノールノボラック型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂、ビスフェノールAノボラック型エポキシ樹脂、ジシクロペンタジエンフェノール型エポキシ樹脂、テルペンフェノール型エポキシ樹脂、フェノールアラルキル型エポキシ樹脂、ビフェニルアラルキル型エポキシ樹脂、ナフトールノボラック型エポキシ樹脂、トリグリシジルアミノフェノール等のグリシジルアミン型エポキシ樹脂、テトラグリシジルジアミニジフェニルメタン型エポキシ樹脂、トリスフェノールメタン型エポキシ樹脂、テトラキスフェノールエタン型エポキシ樹脂などのグリシジルエーテル型エポキシ樹脂、トリグリシジルイソシアヌレート等の複素環式エポキシ樹脂、ヒドロキシベンズアルデヒド、クロトンアルデヒド、グリオキザールなどの種々のアルデヒド類との縮合反応で得られる多価フェノール樹脂、石油系重質油又はピッチ類とホルムアルデヒド重合物とフェノール類とを酸触媒の存在下に重縮合させた変性フェノール樹脂等の各種のフェノール化合物と、エピハロヒドリンとから製造されるエポキシ樹脂、線状脂肪族エポキシ樹脂、脂環式エポキシ樹脂、等の種々のエポキシ樹脂を用いることができる。
本発明においてエポキシ樹脂硬化剤とは、エポキシ樹脂のエポキシ基間の架橋反応及び/又は鎖長延長反応に寄与する物質を示す。本発明においては、通常「硬化促進剤」と呼ばれるものであってもエポキシ樹脂のエポキシ基間の架橋反応及び/又は鎖長延長反応に寄与する物質であれば、硬化剤とみなす。
これらのうち、ポットライフの点で多官能フェノール類、イミダゾール系化合物が好ましく、その中でもイミダゾール系化合物が最も好ましい。
エポキシ樹脂硬化剤の含有量が上記範囲内であると、未反応のエポキシ基や硬化剤の官能基が残留しにくくなるため好ましい。
本発明の硬化性樹脂組成物は、本発明のポリエーテルポリオール樹脂及び3官能以上のエポキシ樹脂以外の、他のエポキシ化合物を含有してもよい。他のエポキシ化合物としては、2官能エポキシ樹脂、例えばビスフェノールA型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、ビスフェノールS型エポキシ樹脂、ビフェニル型エポキシ樹脂などのグリシジルエーテル型エポキシ樹脂、グリシジルエステル型エポキシ樹脂、グリシジルアミン型エポキシ樹脂、線状脂肪族エポキシ樹脂、脂環式エポキシ樹脂、複素環式エポキシ樹脂等の各種のエポキシ樹脂の1種又は2種以上が挙げられる。
本発明の硬化性樹脂組成物には、塗膜形成時等の取り扱い時に、硬化性樹脂組成物の粘度を適度に調整するために溶剤を配合して希釈してもよい。本発明の硬化性樹脂組成物において、溶剤は、硬化性樹脂組成物の成形における取り扱い性、作業性を確保するために用いられ、その使用量には特に制限がない。
本発明においては「溶剤」という語と「溶媒」という語をその使用形態により区別して用いるが、それぞれ独立して同種のものを用いても異なるものを用いてもよい。
本発明の硬化性樹脂組成物には、以上に挙げた成分の他にその他の成分を含有することができる。その他の成分は硬化性樹脂組成物の所望の物性により適宜組み合わせて用いることができる。
靱性を付与するために本発明の硬化性樹脂組成物にゴム粒子、アクリル粒子などの有機充填材を配合してもよい。
無機充填材は固形分としての全エポキシ樹脂成分とエポキシ樹脂硬化剤との合計100質量部に対して、通常10~900質量部配合することができる。
これらは固形分としての全エポキシ樹脂成分とエポキシ樹脂硬化剤との合計100質量部に対して、通常0.1~20質量部配合される。
これら樹脂類を用いる場合、その配合割合は、本発明の硬化性樹脂組成物の本来の性質を損なわない範囲の量、すなわち固形分としての全エポキシ樹脂成分とエポキシ樹脂硬化剤との合計100質量部に対して、50質量部以下が好ましい。
本発明の硬化性樹脂組成物を硬化させることにより、硬化物を得ることができる。ここでいう「硬化」とは熱及び/又は光等によりエポキシ樹脂を意図的に硬化させることを意味する。その硬化の程度は所望の物性、用途により制御すればよい。
本発明のシート状成形体は、本発明の硬化性樹脂組成物を硬化させてなる本発明の硬化物よりなるシート状の成形体である。
本発明の硬化性樹脂組成物は、耐熱性に優れ、更に耐折り曲げ性にも優れた硬化物を与えるものであり、積層板、封止材、接着剤、塗料及び電気絶縁材料等に使用することができる。特に本発明の硬化性樹脂組成物は、センサ、ディスプレイなどの様々なインターフェース用の耐折り曲げ性が必要なデバイス、それを支える基材や、半導体封止用封止材、電気絶縁用粉体塗料、レジストインキ、電気・電子部品用注型材及び電気・電子部品用接着剤及び絶縁フィルム等に使用することができる。本発明の硬化性樹脂組成物は、近年急速に開発が進んでいるフォルダブルOLEDディスプレイに使用されるフィルムの材料としても有用である。
以下の実施例における各種の製造条件や評価結果の値は、本発明の実施態様における上限又は下限の好ましい値としての意味をもつものであり、好ましい範囲は前記した上限又は下限の値と、下記実施例の値又は実施例同士の値との組み合わせで規定される範囲であってもよい。以下において、「部」は全て「質量部」を示す。
以下における各種物性ないし特性の分析・評価・測定方法は次の通りである。
硬化性樹脂組成物の硬化フィルムについて、SIIナノテクノロジー(株)製示差走査熱量計「DSC7020」を使用し、30~200℃まで10℃/minで昇温してガラス転移温度を測定した。ガラス転移温度は、JIS K7121「プラスチックの転移温度測定法」に記載されているうちの「中点ガラス転移温度:Tmg」に基づいて測定した。Tgが140℃未満のものを×、140℃以上のものを〇として評価した。
得られた硬化フィルムについて、ASTM D1925に準じて測色色差計(日本電色工業製、ZE6000)を用いて、YIを測定した。YIが14未満のものを〇、YIが14以上30未満のものを△、YIが30以上又は白濁しているものを×として評価した。
得られた硬化フィルムを180°折り曲げても割れないものを〇、折り曲げることができないものを×として評価した。
<実施例1~3及び比較例1~3>
2官能エポキシ化合物(3,3’,5,5’-テトラメチル-4,4’-ビフェノール型エポキシ樹脂(三菱ケミカル(株)製 商品名「YX4000」、エポキシ当量186g/当量))100部と2価フェノール化合物(ビス(4-ヒドロキシフェニル)-3,3,5-トリメチルシクロヘキサン(水酸基当量155g/当量))80.9部、テトラメチルアンモニウムハイドロオキサイド(27質量%水溶液)0.37部及びメチルエチルケトン(固形分:70質量%)を撹拌機付き耐圧反応容器に入れ、窒素ガス雰囲気下、135℃で8時間反応を行った。反応後、メチルエチルケトンを添加することにより固形分濃度を40質量%に調整した。
こうして得られたポリエーテルポリオール樹脂はエポキシ当量8765g/当量、数平均分子量9,968であった。
・数平均分子量:ゲル浸透クロマトグラフィーによってポリスチレン換算値として測定した。
・エポキシ当量:JIS K7236に準じて電位差滴定法により測定し、樹脂固形分としての値に換算した。
<3官能以上のエポキシ樹脂>
(A-1)トリスフェノールメタン型エポキシ樹脂(三菱ケミカル(株)製 jER1032H60)
(A-2)ビスフェノールAノボラック型エポキシ樹脂(三菱ケミカル(株)製 jER157S65)
(A-3)フェノールノボラック型エポキシ樹脂(三菱ケミカル(株)製 jER154)
(A-4)ビスフェノールF型エポキシ樹脂(三菱ケミカル(株)製 jER806)
(A-5)ビスフェノールA型エポキシ樹脂(三菱ケミカル(株)製 YX4000)
(B-1):2-エチル-4(5)-メチルイミダゾール(三菱ケミカル(株)製 EMI-24)
(B-2):ビスフェノールAノボラック樹脂(三菱ケミカル(株)製 YLH129)
表-1の結果より次のことがわかる。
本発明のポリエーテルポリオール樹脂と3官能以上のエポキシ樹脂を含む本発明の硬化性樹脂組成物を用いて得られた実施例1~3の硬化物は、3官能以上のエポキシ樹脂の代りに2官能のエポキシ樹脂を用いた比較例1~3の硬化物と比較して耐熱性(Tg)に優れたものである。
実施例1~3の硬化性樹脂組成物によれば、比較例1~3の硬化性樹脂組成物と比較して、透明性、可撓性及び耐熱性をバランスよく向上できており、透明性、耐熱性、耐折り曲げ性が要求されるフォルダブルOLEDディスプレイに使用されるフィルム材料としても好適であることが分かる。
本出願は、2018年10月15日付で出願された日本特許出願2018-194395に基づいており、その全体が引用により援用される。
Claims (6)
- 下記一般式(1)で表され、エポキシ当量が7,000~100,000g/当量であるポリエーテルポリオール樹脂と、
3官能以上のエポキシ樹脂と、
エポキシ樹脂硬化剤と
を含み、
前記ポリエーテルポリオール樹脂が、主鎖に芳香族構造を40~55質量%、脂環式構造を8~25質量%含有し、
前記ポリエーテルポリオール樹脂を固形分中に45質量%以上含む硬化性樹脂組成物(なお、主鎖に含有される芳香族構造とは、芳香族構造の芳香環を構成する少なくとも1つの原子が主鎖に含有される芳香族構造であり、また、主鎖に含有される脂環式構造とは、脂環式構造の脂環を構成する少なくとも1つの原子が主鎖に含有される脂環式構造である)。
一般式(1)中、nは1以上の整数である。A1及びA2は互いに同一でも異なっていてもよく、下記一般式(3)で表される基である。Bは水素原子又は下記式(2)で表される基である。2つのBのうちの少なくとも一方は下記式(2)で表される基である。
一般式(3)中、R 1 は互いに同一であっても異なっていてもよく水素原子、炭素数1~10の炭化水素基又はハロゲン原子から選ばれる基である。Xは単結合、炭素数1~7の2価の炭化水素基、シクロヘキサン環構造又はトリメチルシクロヘキサン環構造を有する2価の有機基、-O-、-S-、-SO 2 -、及び-C(O)-から選ばれる2価の基である。但し、少なくともA 1 及びA 2 中のいずれかのXはシクロヘキサン環構造又はトリメチルシクロヘキサン環構造を有する2価の基である。
- 前記ポリエーテルポリオール樹脂の数平均分子量が9,000~40,000である請求項1に記載の硬化性樹脂組成物。
- 2官能エポキシ樹脂とビス(4-ヒドロキシフェニル)-3,3,5-トリメチルシクロヘキサンを反応させて前記ポリエーテルポリオール樹脂を製造する工程を含む請求項1又は2に記載の硬化性樹脂組成物の製造方法。
- 請求項1~3のいずれかに記載の硬化性樹脂組成物を硬化させてなる硬化物。
- 請求項4に記載の硬化物からなるシート状成形体。
- Tgが140℃以上である請求項5に記載のシート状成形体。
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