JP2020066643A - 光カチオン硬化型エポキシ樹脂組成物 - Google Patents
光カチオン硬化型エポキシ樹脂組成物 Download PDFInfo
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- 239000000203 mixture Substances 0.000 title claims abstract description 28
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 23
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 22
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims abstract description 15
- -1 cyclic ether compound Chemical class 0.000 claims abstract description 14
- 239000004593 Epoxy Substances 0.000 claims abstract description 13
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 9
- 238000007789 sealing Methods 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims description 5
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 claims description 4
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 7
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- 125000002091 cationic group Chemical group 0.000 description 6
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000005452 bending Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 230000000630 rising effect Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 238000010538 cationic polymerization reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XQQZRZQVBFHBHL-UHFFFAOYSA-N 12-crown-4 Chemical compound C1COCCOCCOCCO1 XQQZRZQVBFHBHL-UHFFFAOYSA-N 0.000 description 1
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 1
- UZYFEQIMORYGRW-UHFFFAOYSA-N 2-[(2-tert-butylphenoxy)methyl]oxirane Chemical compound CC(C)(C)C1=CC=CC=C1OCC1OC1 UZYFEQIMORYGRW-UHFFFAOYSA-N 0.000 description 1
- HSDVRWZKEDRBAG-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COC(CCCCC)OCC1CO1 HSDVRWZKEDRBAG-UHFFFAOYSA-N 0.000 description 1
- HIGURUTWFKYJCH-UHFFFAOYSA-N 2-[[1-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane Chemical compound C1OC1COCC1(COCC2OC2)CCCCC1 HIGURUTWFKYJCH-UHFFFAOYSA-N 0.000 description 1
- MSXXDBCLAKQJQT-UHFFFAOYSA-N 2-tert-butyl-6-methyl-4-[3-(2,4,8,10-tetratert-butylbenzo[d][1,3,2]benzodioxaphosphepin-6-yl)oxypropyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCCOP2OC3=C(C=C(C=C3C=3C=C(C=C(C=3O2)C(C)(C)C)C(C)(C)C)C(C)(C)C)C(C)(C)C)=C1 MSXXDBCLAKQJQT-UHFFFAOYSA-N 0.000 description 1
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical group C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910018286 SbF 6 Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001723 carbon free-radicals Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000010227 cup method (microbiological evaluation) Methods 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- OWZDULOODZHVCQ-UHFFFAOYSA-N diphenyl-(4-phenylsulfanylphenyl)sulfanium Chemical compound C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 OWZDULOODZHVCQ-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 230000037050 permeability transition Effects 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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- Epoxy Resins (AREA)
Abstract
Description
(B)の粘度は25℃での測定値とする。
遮光ビンに、前記(A)としてEPICLOEXA−830LVP(商品名:DIC社製、エポキシ当量156〜168g/eq、ビスフェノールF型)及びEPICLON 850CRP(商品名:DIC社製、エポキシ当量168〜178g/eq、ビスフェノールA型)を、(B)としてEX−214(商品名:ナガセケムテックス社製、1、4ブタンジオールジグリシジルエーテル、粘度15mPa・s)及びYED216D(商品名:三菱化学社製、1,6ヘキサンジオールジグリシジルエーテル、粘度15mPa・s)を、(C)としてクラウンエーテルO−18(商品名:日本曹達社製、18−クラウンー6)を、(D)CPI−210S(商品名:サンアプロ社製、ジフェニル[4−(フェニルチオ)フェニル]スルホニウム トリス(ペンタフルオロエチル)トリフルオロホスフェート)をとして、酸化防止剤としてsumilizerGP(商品名:住友化学社製)を、表1に示す量入れ、撹拌脱泡器を用いて均一になるまで撹拌して実施例1〜5の光カチオン硬化型エポキシ樹脂組成物を得た。なお配合表の単位は重量部とする。
実施例で用いた材料の他、前記(A)としてYL983U(商品名:三菱化学社製、エポキシ当量165〜175g/eq、ビスフェノールF型)を、水添ビスフェノールA型ジグリシジルエーテルとしてYX8000(商品名:三菱化学社製、エポキシ当量205g/eq)を、前記(B)としてEX−216(商品名:ナガセケムテック社製、シクロヘキサンジメタノールジグリシジルエーテル、粘度65mPa・s)及びED−509S(商品名:アデカ社製、tブチルフェノールグリシジルエーテル)を、表1に示す量入れ、撹拌脱泡器を用いて均一になるまで撹拌して比較例1〜4の光カチオン硬化型エポキシ樹脂組成物を得た。
上記で得られた樹脂組成物を1mmの厚さで塗工し、LED−UV(パナソニック社製)を用い、365nmで100mW/cm2、露光量2000mJ/cm2の照射条件で露光後、70℃の恒温器内で30分後硬化し、試験片とした。
評価結果を表2に示す。
Claims (4)
- エポキシ当量の平均が156〜180g/eqであるビスフェノール骨格ジグリシジルエーテル(A)と、アルキル骨格ジグリシジルエーテル(B)と、環状エーテル化合物(C)と、光カチオン重合開始剤(D)と、を含み、E型粘度計で測定された25℃、50rpmにおける粘度が10〜50mPa・sであることを特徴とする光カチオン硬化型エポキシ樹脂組成物。
- 前記(B)が1,4ブタンジオールジグリシジルエーテル及び/又は1,6ヘキサンジオールジグリシジルエーテルを含むことを特徴とする請求項1記載の光カチオン硬化型エポキシ樹脂組成物。
- 前記(C)が18−クラウン−6であることを特徴とする請求項1又は2いずれか記載の光カチオン硬化型エポキシ樹脂組成物。
- 有機EL素子の封止用樹脂であることを特徴とする請求項1〜3いずれか記載の光カチオン硬化型エポキシ樹脂組成物。
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Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0216179A (ja) * | 1988-05-02 | 1990-01-19 | Henkel Kgaa | 光で誘起されて暗所で硬化する接着剤 |
JPH0491169A (ja) * | 1990-08-06 | 1992-03-24 | Yokohama Rubber Co Ltd:The | 電子材料用樹脂組成物 |
JP2010018797A (ja) * | 2008-06-11 | 2010-01-28 | Sekisui Chem Co Ltd | 光学部品用硬化性組成物、光学部品用接着剤及び有機エレクトロルミネッセンス素子用封止剤 |
JP2010248387A (ja) * | 2009-04-16 | 2010-11-04 | Sekisui Chem Co Ltd | 光学部材用光硬化性樹脂組成物、接着剤、及び、タッチパネル |
JP2011107825A (ja) * | 2009-11-13 | 2011-06-02 | Sekisui Chem Co Ltd | タッチパネル用光硬化性樹脂組成物、タッチパネルの製造方法、及び、タッチパネル |
JP2011111598A (ja) * | 2009-11-30 | 2011-06-09 | Sekisui Chem Co Ltd | タッチパネル用光硬化性樹脂組成物及びタッチパネル |
WO2014199626A1 (ja) * | 2013-06-10 | 2014-12-18 | 三井化学株式会社 | 熱硬化性組成物、有機el素子用面封止剤およびその硬化物 |
WO2016158522A1 (ja) * | 2015-03-27 | 2016-10-06 | 株式会社Adeka | 組成物 |
-
2018
- 2018-10-22 JP JP2018198101A patent/JP7128716B2/ja active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0216179A (ja) * | 1988-05-02 | 1990-01-19 | Henkel Kgaa | 光で誘起されて暗所で硬化する接着剤 |
JPH0491169A (ja) * | 1990-08-06 | 1992-03-24 | Yokohama Rubber Co Ltd:The | 電子材料用樹脂組成物 |
JP2010018797A (ja) * | 2008-06-11 | 2010-01-28 | Sekisui Chem Co Ltd | 光学部品用硬化性組成物、光学部品用接着剤及び有機エレクトロルミネッセンス素子用封止剤 |
JP2010248387A (ja) * | 2009-04-16 | 2010-11-04 | Sekisui Chem Co Ltd | 光学部材用光硬化性樹脂組成物、接着剤、及び、タッチパネル |
JP2011107825A (ja) * | 2009-11-13 | 2011-06-02 | Sekisui Chem Co Ltd | タッチパネル用光硬化性樹脂組成物、タッチパネルの製造方法、及び、タッチパネル |
JP2011111598A (ja) * | 2009-11-30 | 2011-06-09 | Sekisui Chem Co Ltd | タッチパネル用光硬化性樹脂組成物及びタッチパネル |
WO2014199626A1 (ja) * | 2013-06-10 | 2014-12-18 | 三井化学株式会社 | 熱硬化性組成物、有機el素子用面封止剤およびその硬化物 |
WO2016158522A1 (ja) * | 2015-03-27 | 2016-10-06 | 株式会社Adeka | 組成物 |
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