JP5129924B2 - 遮光性を有する光硬化性樹脂組成物及びその硬化物 - Google Patents
遮光性を有する光硬化性樹脂組成物及びその硬化物 Download PDFInfo
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- JP5129924B2 JP5129924B2 JP2005316651A JP2005316651A JP5129924B2 JP 5129924 B2 JP5129924 B2 JP 5129924B2 JP 2005316651 A JP2005316651 A JP 2005316651A JP 2005316651 A JP2005316651 A JP 2005316651A JP 5129924 B2 JP5129924 B2 JP 5129924B2
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- INXWLSDYDXPENO-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CO)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C INXWLSDYDXPENO-UHFFFAOYSA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
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- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
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- 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
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
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- 230000001588 bifunctional effect Effects 0.000 description 1
- IDSLNGDJQFVDPQ-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-yl) hexanedioate Chemical compound C1CC2OC2CC1OC(=O)CCCCC(=O)OC1CC2OC2CC1 IDSLNGDJQFVDPQ-UHFFFAOYSA-N 0.000 description 1
- DJUWPHRCMMMSCV-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-ylmethyl) hexanedioate Chemical compound C1CC2OC2CC1COC(=O)CCCCC(=O)OCC1CC2OC2CC1 DJUWPHRCMMMSCV-UHFFFAOYSA-N 0.000 description 1
- XFUOBHWPTSIEOV-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohexane-1,2-dicarboxylate Chemical compound C1CCCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 XFUOBHWPTSIEOV-UHFFFAOYSA-N 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
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- OUWGYAHTVDEVRZ-UHFFFAOYSA-N butane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(O)CCO OUWGYAHTVDEVRZ-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- DNWBGZGLCKETOT-UHFFFAOYSA-N cyclohexane;1,3-dioxane Chemical compound C1CCCCC1.C1COCOC1 DNWBGZGLCKETOT-UHFFFAOYSA-N 0.000 description 1
- BXCOOPLIKAAONJ-UHFFFAOYSA-N di(propan-2-yl)diazene Chemical compound CC(C)N=NC(C)C BXCOOPLIKAAONJ-UHFFFAOYSA-N 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229940117969 neopentyl glycol Drugs 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000011022 opal Substances 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920002717 polyvinylpyridine Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
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- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- UXKIKTPOJMDBEZ-UHFFFAOYSA-N tetrakis(7-oxabicyclo[4.1.0]heptan-4-ylmethyl) butane-1,1,1,2-tetracarboxylate Chemical compound C1CC2OC2CC1COC(=O)C(C(=O)OCC1CC2OC2CC1)(C(=O)OCC1CC2OC2CC1)C(CC)C(=O)OCC1CC2OC2CC1 UXKIKTPOJMDBEZ-UHFFFAOYSA-N 0.000 description 1
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- XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 description 1
Images
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- Compositions Of Macromolecular Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
(1)光硬化性樹脂及び該光硬化性樹脂の硬化物の屈折率との屈折率の差が0.01以上となる屈折率を有し、該光硬化性樹脂に対して非相溶性で分散性を有する化合物を含む光硬化性樹脂組成物;
(2)屈折率の差が0.1以上である、上記(1)記載の光硬化性樹脂組成物;
(3)光硬化性樹脂がアクリル変性樹脂又はエポキシ樹脂である、上記(1)又は(2)記載の光硬化性樹脂組成物;
(4)さらに、光重合開始剤を含む、上記(1)〜(3)のいずれか1項記載の光硬化性樹脂組成物;
(5)上記(1)〜(4)のいずれか1項記載の光重合性樹脂組成物の硬化物;
(6)上記(5)記載の硬化物を含む光学機器部材;
(7)上記(6)記載の光学機器部材を含む光学機器
である。
ZnO(屈折率1.90)、TiO2 (屈折率2.3〜2.7)、CeO2 (屈折率1.95)、Sb2 O5 (屈折率1.71)、SnO2 、ITO(屈折率1.95)、Y2 O3 (屈折率1.87)、La2 O3 (屈折率1.95)、ZrO2 (屈折率2.05)、Al2 O3 (屈折率1.63)、メラミン樹脂(1.6)、ナイロン(1.53)、ポリスチレン(1.6)、ポリエチレン(1.53)、ポリテトラフルオロエチレン(1.35)、メタクリル酸メチル樹脂(1.49)、塩化ビニル樹脂(1.54)、シリコーン油(1.4)
表1に示す割合で、ウレタンアクリレート樹脂(U-4HA、新中村化学社製)と光重合開始剤(I-184、CIBA CHWMICALS社製)を常法に従って混合しアクリル系ベース樹脂Aを、また、エポキシ樹脂(EP-830S、大日本インキ化学社製)と光重合開始剤(SP150、サンアプロ社製)を常法に従って混合しエポキシ系ベース樹脂Bを得た。さらに表2に示す割合で、作製したベース樹脂と各種材料を常法に従って混合し、光硬化性遮光樹脂組成物を得た。具体的には、室温のアクリル系ベース樹脂Aの100重量部を容器に装入した後、20重量部の球状アルミナを添加し500rpmの撹拌条件下、23℃で15分撹拌した。
表2に示すような割合で、実施例1と同様にして、混合し光硬化性樹脂組成物を得た。ベース樹脂A及びBのみからなる光硬化性樹脂組成物を参考例1及び2とした。
高屈折率化合物及び低屈折率化合物の代わりにカーボンブラックを加える以外は、実施例1と全く同様に操作し、表5に示すような割合で光硬化性樹脂組成物を得た。これらを実施例1と同様に評価し、その結果を表6に示す。
E:遮光スペーサ、F:遮光性固定(封止)樹脂
1:入射光、2:外部透過光、3:内部透過光(損失光)
Claims (6)
- 光硬化性樹脂100重量部及び該光硬化性樹脂の硬化物の屈折率との屈折率の差が0.1以上となる屈折率を有し、該光硬化性樹脂に対して非相溶性で分散性を有する化合物の粒子1〜20重量部を含み、黒色顔料を含まない光硬化性遮光樹脂組成物であって、該化合物粒子の粒子径が0.1〜100μmであり、0.5μmの膜厚において、光硬化性遮光樹脂組成物の硬化物が1%以下の300〜800nmにおける光透過率を有する、光硬化性遮光樹脂組成物。
- 光硬化性樹脂がアクリル変性樹脂又はエポキシ樹脂である、請求項1記載の光硬化性遮光樹脂組成物。
- さらに、光重合開始剤を含む、請求項1又は2記載の光硬化性遮光樹脂組成物。
- 請求項1〜3のいずれか1項記載の光重合性遮光樹脂組成物の硬化物。
- 請求項4記載の硬化物を含む光学機器部材。
- 請求項5記載の光学機器部材を含む光学機器。
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