JP2020169290A - 光硬化性樹脂組成物 - Google Patents
光硬化性樹脂組成物 Download PDFInfo
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- JP2020169290A JP2020169290A JP2019072378A JP2019072378A JP2020169290A JP 2020169290 A JP2020169290 A JP 2020169290A JP 2019072378 A JP2019072378 A JP 2019072378A JP 2019072378 A JP2019072378 A JP 2019072378A JP 2020169290 A JP2020169290 A JP 2020169290A
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- 239000011347 resin Substances 0.000 claims abstract description 31
- 229920005989 resin Polymers 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 21
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 claims abstract description 14
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims abstract description 13
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 12
- 239000007787 solid Substances 0.000 claims abstract description 12
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- 230000001681 protective effect Effects 0.000 claims abstract description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 33
- 238000002156 mixing Methods 0.000 claims description 12
- 125000002723 alicyclic group Chemical group 0.000 claims description 10
- 229920001195 polyisoprene Polymers 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 8
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 4
- -1 adamantanyl Chemical group 0.000 description 4
- 239000005357 flat glass Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
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- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- OLAQBFHDYFMSAJ-UHFFFAOYSA-L 1,2-bis(7-methyloctyl)cyclohexane-1,2-dicarboxylate Chemical compound CC(C)CCCCCCC1(C([O-])=O)CCCCC1(CCCCCCC(C)C)C([O-])=O OLAQBFHDYFMSAJ-UHFFFAOYSA-L 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
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- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- HORIEOQXBKUKGQ-UHFFFAOYSA-N bis(7-methyloctyl) cyclohexane-1,2-dicarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCC(C)C HORIEOQXBKUKGQ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 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 2
- 239000004806 diisononylester Substances 0.000 description 2
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- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- JMIZWXDKTUGEES-UHFFFAOYSA-N 2,2-di(cyclopenten-1-yloxy)ethyl 2-methylprop-2-enoate Chemical compound C=1CCCC=1OC(COC(=O)C(=C)C)OC1=CCCC1 JMIZWXDKTUGEES-UHFFFAOYSA-N 0.000 description 1
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical group CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 1
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 241001566735 Archon Species 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000013032 Hydrocarbon resin Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- URLYGBGJPQYXBN-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methyl prop-2-enoate Chemical compound OCC1CCC(COC(=O)C=C)CC1 URLYGBGJPQYXBN-UHFFFAOYSA-N 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
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- 239000013078 crystal Substances 0.000 description 1
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- 230000000694 effects Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- RNCMBSSLYOAVRT-UHFFFAOYSA-N monoisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(O)=O RNCMBSSLYOAVRT-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
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- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000037303 wrinkles Effects 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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- Liquid Crystal (AREA)
- Polymerisation Methods In General (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Abstract
Description
非反応成分としてアルコンP90(商品名:荒川化学工業社製、完全水素添加石油樹脂)及びDINCH(商品名:BASFジャパン社製、1,2−シクロヘキサンジカルボン酸ジイソノニルエステル)を、反応成分としてUC−203M(商品名:クラレ社製、ポリイソプレン重合物の無水マレイン酸付加物と2-ヒドロキシエチルメタアクリレートとのエステル化物、3官能、Mn30,000)及びFA−512M(商品名:日立化成社製、ジシクロペンテニルオキシエチルメタクリレート)及び4HBA(商品名:大阪有機化学工業社製、4ヒドロキシブチルアクリレート)を、光重合開始剤としてOmnirad184(商品名:IGM製、α−ヒドロキシアセトフェノン系)及びTPOH(商品名:IGM製、アシルフォスフィンオキサイド系)を、重合禁止剤としてHQ(ハイドロキノン)及びMHQ(メチルハイドロキノン)を、表1記載の配合で均一に溶解するまで撹拌し、実施例1〜6の光硬化性樹脂組成物を調製した。
実施例で用いた材料の他、重合禁止剤としてBHT(ターシャリーブチルヒドロキシトルエン)及びMEHQ(4メトキシフェノール)及びBQ(ベンゾキノン)を、表1記載の配合で均一に溶解するまで撹拌し比較例1〜7の光硬化性樹脂組成物を調整した。
表2
Claims (5)
- 光重合開始剤と、ハイドロキノンと/又はメチルハイドロキノンからなる反応禁止剤を含む組成物であって、組成物の固形分100重量部に対する非反応性成分の配合量が30〜50重量部であり、反応性成分100重量部に対する重合禁止剤の配合量が0.1〜0.4重量部であることを特徴とする光硬化型樹脂組成物。
- 前記反応性成分がポリイソプレン多官能(メタ)アクリレートオリゴマーを含むことを特徴とする請求項1記載の光硬化型樹脂組成物。
- 前記非反応性成分が常温で固体の脂環族樹脂を含むことを特徴とする請求項1又は2いずれか記載の光硬化型樹脂組成物。
- 液晶パネルと保護基材との間に封入されることを特徴とする請求項1〜3いずれか記載の光硬化型樹脂組成物。
- 請求項1〜4いずれか記載の光硬化型樹脂組成物を用い、ブラックライト光源による仮硬化後、更に他紫外線光源による硬化を行う特徴とする光硬化型樹脂組成物の硬化方法。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002040647A (ja) * | 2000-07-31 | 2002-02-06 | Taiyo Ink Mfg Ltd | レジストインキ組成物 |
JP2012073601A (ja) * | 2010-08-31 | 2012-04-12 | Fujifilm Corp | 感光性組成物、並びに、感光性フィルム、永久パターン、永久パターン形成方法、及びプリント基板 |
JP2016066004A (ja) * | 2014-09-25 | 2016-04-28 | 日立化成株式会社 | 感光性樹脂組成物 |
WO2017122717A1 (ja) * | 2016-01-12 | 2017-07-20 | 日立化成株式会社 | 感光性樹脂組成物、それを用いたドライフィルム、プリント配線板、及びプリント配線板の製造方法 |
JP2017135388A (ja) * | 2016-01-21 | 2017-08-03 | 山栄化学株式会社 | 物への表面表示・模様の形成方法 |
-
2019
- 2019-04-05 JP JP2019072378A patent/JP7295689B2/ja active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002040647A (ja) * | 2000-07-31 | 2002-02-06 | Taiyo Ink Mfg Ltd | レジストインキ組成物 |
JP2012073601A (ja) * | 2010-08-31 | 2012-04-12 | Fujifilm Corp | 感光性組成物、並びに、感光性フィルム、永久パターン、永久パターン形成方法、及びプリント基板 |
JP2016066004A (ja) * | 2014-09-25 | 2016-04-28 | 日立化成株式会社 | 感光性樹脂組成物 |
WO2017122717A1 (ja) * | 2016-01-12 | 2017-07-20 | 日立化成株式会社 | 感光性樹脂組成物、それを用いたドライフィルム、プリント配線板、及びプリント配線板の製造方法 |
JP2017135388A (ja) * | 2016-01-21 | 2017-08-03 | 山栄化学株式会社 | 物への表面表示・模様の形成方法 |
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