JP6688063B2 - 光硬化性樹脂組成物および積層体 - Google Patents
光硬化性樹脂組成物および積層体 Download PDFInfo
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- JP6688063B2 JP6688063B2 JP2015246081A JP2015246081A JP6688063B2 JP 6688063 B2 JP6688063 B2 JP 6688063B2 JP 2015246081 A JP2015246081 A JP 2015246081A JP 2015246081 A JP2015246081 A JP 2015246081A JP 6688063 B2 JP6688063 B2 JP 6688063B2
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- 239000000203 mixture Substances 0.000 claims description 11
- 239000012788 optical film Substances 0.000 claims description 8
- JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 claims description 6
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
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- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 2
- 206010070835 Skin sensitisation Diseases 0.000 description 2
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- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
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- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
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- 239000011347 resin Substances 0.000 description 2
- 231100000370 skin sensitisation Toxicity 0.000 description 2
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- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- JTINZFQXZLCHNS-UHFFFAOYSA-N 2,2-bis(oxiran-2-ylmethoxymethyl)butan-1-ol Chemical compound C1OC1COCC(CO)(CC)COCC1CO1 JTINZFQXZLCHNS-UHFFFAOYSA-N 0.000 description 1
- BZUILZIKDIMXBK-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxycarbonyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OCC1OC1 BZUILZIKDIMXBK-UHFFFAOYSA-N 0.000 description 1
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 1
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 description 1
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-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
- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 description 1
- NHJIDZUQMHKGRE-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 2-(7-oxabicyclo[4.1.0]heptan-4-yl)acetate Chemical compound C1CC2OC2CC1OC(=O)CC1CC2OC2CC1 NHJIDZUQMHKGRE-UHFFFAOYSA-N 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- NIYNIOYNNFXGFN-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol;7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound OCC1CCC(CO)CC1.C1C(C(=O)O)CCC2OC21.C1C(C(=O)O)CCC2OC21 NIYNIOYNNFXGFN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polarising Elements (AREA)
Description
遮光ビンに、前記(A)として、EXA−830LVP(商品名:DIC社製、ビスフェノールFジグリシジルエーテル、エポキシ当量:160)を、前記(B)として、EX−214L(商品名:ナガセケムテックス社製、ブタンジールジグリシジルエーテル、エポキシ当量:120)を、前記(C)として、セロキサイド2021P(商品名:ダイセル社製、3,4エポキシシクロへキシルメチル,3,4エポキシシクロへキサンカルボキシ
レート)を、前記(D)として、CPI−110P(商品名:サンアプロ社製、スルホニウム塩系光酸発生剤)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の光硬化性樹脂組成物を得た。
参考例1で使用した材料のほか、前記(A)として、EX−721P(商品名:ナガセケムテックス社製、フタル酸シグリシジルエステル、エポキシ当量:154)を、前記(B)として、EX−722P(商品名:ナガセケムテックス社製、水添フタル酸ジグリシジルエステル、エポキシ当量:158)を、前記(C)として、セロキサイド8000(商品名:ダイセル社製、(3,3’,4,4’−ジエポキシ)ビシクロヘキシル)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実施例2〜10の光硬化性樹脂組成物を得た。
実施例で用いた材料の他、前記(B)として、EX−211L(商品名:ナガセケムテック社製、ネオペンチルグリコールジグリシジルエーテル、エポキシ当量:130)を、単官能脂肪族エポキシとして、EX−121(商品名:ナガセケムテック社製、2-エチルヘキシルグリシジルエステル、エポキシ当量:187)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1〜8の光硬化性樹脂組成物を得た。
光硬化性樹脂組成物の被着体となるTACフィルム(富士フィルム社製、60μm)およびCOPフィルム(日本ゼオン社製50μm)に、春日井電機製のコロナ表面改質評価装置TEC−4AXを用い水の接触角が飽和するまでコロナ照射する。コロナ照射処理をおこなったTACフィルム上に光硬化性樹脂組成物を滴下し、直ちにヨウ素を含浸し延伸偏光したPVAフィルムを重ね、更に当該PVAフィルム上に光硬化性樹脂組成物を滴下し、直ちにCOPフィルムを貼り合せる。この状態でCOPフィルム面から、フュージョンUVシステムズジャパン製の無電極UV照射装置F300S/LC−6Bを用い、Dバルブで出力250mW/cm2、積算光量が200mJ/cm2となる様に紫外線照射硬化させ、その後80℃の恒温器で3分間硬化させ、偏光フィルムを作成し試験体とした。
放置後の粘度を測定し、初期粘度に対し増粘しないものを○、増粘したものを×とした。
評価結果を表2に示す。
Claims (3)
- 分子中に複数のエポキシ基を有する芳香族化合物(A)と、分子中に複数のエポキシ基を有する脂肪族化合物(B)と、脂環式エポキシ(C)と、光カチオン重合開始剤(D)と、を含み、前記(A)がビスフェノールFジグリシジルエーテルとフタル酸ジグリシジルエステルを含み、前記(B)の含有量が全組成分100重量部に対し30重量部以上60重量部未満である光硬化性樹脂組成物。
- 前記(A)のビスフェノールFジグリシジルエーテル:フタル酸ジグリシジルエステルの配合比率が、2.1〜5.1:1であることを特徴とする光硬化性樹脂組成物。
- 請求項1または2記載の光硬化性樹脂組成物層と、偏光子と、保護フィルムと、を少なくとも含む光学フィルム積層体。
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JP2015199083 | 2015-10-07 | ||
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JP2017071745A JP2017071745A (ja) | 2017-04-13 |
JP6688063B2 true JP6688063B2 (ja) | 2020-04-28 |
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Publication number | Priority date | Publication date | Assignee | Title |
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EP1966306A4 (en) * | 2005-10-25 | 2011-12-14 | Henkel Corp | LOW EXOTHERMIC THERMOSETTING RESIN COMPOSITIONS USEFUL AS LOW-BULK MATERIALS WITH REPLACEMENT CAPABILITY |
JP5640030B2 (ja) * | 2012-03-08 | 2014-12-10 | 協立化学産業株式会社 | 積層フィルムの製造方法 |
KR102155921B1 (ko) * | 2013-02-20 | 2020-09-14 | 스미또모 가가꾸 가부시키가이샤 | 광경화성 접착제, 및 그것을 이용한 편광판, 적층 광학 부재 및 액정 표시 장치 |
JP6400005B2 (ja) * | 2013-07-09 | 2018-10-03 | 株式会社Adeka | カチオン重合性組成物 |
KR102219443B1 (ko) * | 2013-07-09 | 2021-02-25 | 가부시키가이샤 아데카 | 양이온 중합성 조성물 |
JP6571318B2 (ja) * | 2014-07-10 | 2019-09-04 | サムスン エスディアイ カンパニー,リミテッドSamsung Sdi Co.,Ltd. | 偏光板用接着剤およびこれを用いた表示装置 |
JP6802708B2 (ja) * | 2014-09-29 | 2020-12-16 | 株式会社Adeka | 光硬化性接着剤、並びにそれを用いた偏光板、積層光学部材及び液晶表示装置 |
WO2016158522A1 (ja) * | 2015-03-27 | 2016-10-06 | 株式会社Adeka | 組成物 |
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