JP2016166262A - 不飽和エステル基含有エポキシ樹脂 - Google Patents
不飽和エステル基含有エポキシ樹脂 Download PDFInfo
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- JP2016166262A JP2016166262A JP2015045553A JP2015045553A JP2016166262A JP 2016166262 A JP2016166262 A JP 2016166262A JP 2015045553 A JP2015045553 A JP 2015045553A JP 2015045553 A JP2015045553 A JP 2015045553A JP 2016166262 A JP2016166262 A JP 2016166262A
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- Prior art keywords
- ester group
- unsaturated ester
- meth
- epoxy resin
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000004185 ester group Chemical group 0.000 title claims abstract description 46
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 39
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 39
- 239000004593 Epoxy Substances 0.000 claims abstract description 35
- 239000000463 material Substances 0.000 claims abstract description 22
- 229920005989 resin Polymers 0.000 claims abstract description 22
- 239000011347 resin Substances 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 9
- 239000007800 oxidant agent Substances 0.000 claims description 7
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims description 7
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- 150000002894 organic compounds Chemical class 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003505 polymerization initiator Substances 0.000 claims description 3
- 238000006735 epoxidation reaction Methods 0.000 claims 1
- -1 acryl unit Chemical group 0.000 abstract description 33
- 238000003860 storage Methods 0.000 abstract description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 32
- 239000000203 mixture Substances 0.000 description 22
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 230000000052 comparative effect Effects 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 150000001451 organic peroxides Chemical class 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- JZBWUTVDIDNCMW-UHFFFAOYSA-L dipotassium;oxido sulfate Chemical compound [K+].[K+].[O-]OS([O-])(=O)=O JZBWUTVDIDNCMW-UHFFFAOYSA-L 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000007870 radical polymerization initiator Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- FYYIUODUDSPAJQ-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 2-methylprop-2-enoate Chemical compound C1C(COC(=O)C(=C)C)CCC2OC21 FYYIUODUDSPAJQ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-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
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 description 2
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 2
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
- NCAVPEPBIJTYSO-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate;2-(oxiran-2-ylmethoxymethyl)oxirane Chemical compound C1OC1COCC1CO1.OCCCCOC(=O)C=C NCAVPEPBIJTYSO-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
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- 239000002994 raw material Substances 0.000 description 2
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- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
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- 229920001187 thermosetting polymer Polymers 0.000 description 2
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Abstract
【解決手段】分子中に、エポキシユニットと、(メタ)アクリルユニットとを含有する、不飽和エステル基含有エポキシ樹脂であって、
エポキシユニットが10〜90重量%であり、
(メタ)アクリルユニットが90〜10重量%である不飽和エステル基含有エポキシ樹脂を用いること。
【選択図】図1
Description
エポキシユニットが10〜90重量%であり、(メタ)アクリルユニットが90〜10重量%である不飽和エステル基含有エポキシ樹脂が、透明性および保存安定性に優れることを見出した。本発明はこれらの知見に基づいて完成させたものである。
エポキシユニットが10〜90重量%であり、
(メタ)アクリルユニットが90〜10重量%である不飽和エステル基含有エポキシ樹脂に関する。
式(A)
一般式(2)
一般式(3)
nは1〜6までの整数を表す。)
エポキシユニットが10〜90重量%であり、
(メタ)アクリルユニットが90〜10重量%である。
また、(メタ)アクリレート化合物には重合性オリゴマーである各種のエポキシアクリレート、ウレタン(メタ)アクリレート、不飽和ポリエステルやポリエステル(メタ)アクリレート及びポリエーテル(メタ)アクリレートも含まれる。
攪拌機、温度計を備えた反応容器に、トリメチロールプロパン2.6部、4−ビニルシクロヘキセン−1−オキサイド28.5部を仕込み70℃で加熱攪拌した。トリメチロールプロパン溶解後、室温まで放冷し、グリシジルメタクリレート8.14部、4−メトキシフェノール0.05部を仕込み攪拌した。三フッ化ホウ素ジエチルエーテル錯体0.8部と酢酸エチル15.5部を混合し、1時間かけてゆっくり滴下して加えた。室温で2時間反応させ1H−NMRで反応が完結しているのを確認した。同じ反応容器に、炭酸水素ナトリウム109.1部、アセトン241.8部、水220部を仕込み、室温で攪拌した。オキソン(ペルオキシ硫酸カリウム複塩)155.0部を4分割して2時間ごとに加えた。室温で一晩反応後、水を加えて酢酸エチルで抽出、水洗後、硫酸マグネシウムで乾燥し、固形分19.6%の不飽和エステル基含有エポキシ樹脂の酢酸エチル溶液を158.8g得た。収率72.6%。
攪拌機、温度計を備えた反応容器に、トリメチロールプロパン2.4部、4−ビニルシクロヘキセン−1−オキサイド26.3部を仕込み70℃で加熱攪拌した。トリメチロールプロパン溶解後、室温まで放冷し、4−ヒドロキシブチルアクリレートグリシジルエーテル10.6部、4−メトキシフェノール0.04部を仕込み攪拌した。三フッ化ホウ素ジエチルエーテル錯体0.7部と酢酸エチル14.5部を混合し、1時間かけてゆっくり滴下して加えた。室温で2時間反応させ1H−NMRで反応が完結しているのを確認した。同じ反応容器に、炭酸水素ナトリウム101.1部、アセトン218.7部、水210部を仕込み、室温で攪拌した。オキソン(ペルオキシ硫酸カリウム複塩)143.5部を4分割して2時間ごとに加えた。室温で一晩反応後、水を加えて酢酸エチルで抽出、水洗後、硫酸マグネシウムで乾燥し、固形分61.8%の不飽和エステル基含有エポキシ樹脂の酢酸エチル溶液を39.9g得た。収率93.7%。
攪拌機、温度計を備えた反応容器に、トリメチロールプロパン2.4部、4−ビニルシクロヘキセン−1−オキサイド26.4部を仕込み70℃で加熱攪拌した。トリメチロールプロパン溶解後、室温まで放冷し、3,4−エポキシシクロへキシルメチルメタクリレート10.4部、4−メトキシフェノール0.04部を仕込み攪拌した。三フッ化ホウ素ジエチルエーテル錯体0.7部と酢酸エチル15.5部を混合し、1時間かけてゆっくり滴下して加えた。室温で2時間反応させ1H−NMRで反応が完結しているのを確認した。50℃に加熱後、過酢酸41.69部を4時間かけてゆっくり滴下して加えた。そのまま3時間加熱攪拌して反応を進行させ、1H−NMRで反応が完結しているのを確認した。放冷後、亜硫酸ナトリウム水溶液を加えて酢酸エチルで抽出、次に炭酸水素ナトリウムを加えて酢酸エチルで抽出、最後に飽和食塩水で洗浄した。硫酸マグネシウムで乾燥し、固形分42.0%の不飽和エステル基含有エポキシ樹脂の酢酸エチル溶液を53.5g得た。収率53.1%。
攪拌機、温度計を備えた反応容器に、トリメチロールプロパン2.2部、4−ビニルシクロヘキセン−1−オキサイド18.1部を仕込み70℃で加熱攪拌した。トリメチロールプロパン溶解後、室温まで放冷し、3,4−エポキシシクロへキシルメチルメタクリレート19.1部、4−メトキシフェノール0.04部を仕込み攪拌した。三フッ化ホウ素ジエチルエーテル錯体0.7部と2−アセトキシ−1−メトキシプロパン15.5部を混合し、1時間かけてゆっくり滴下して加えた。室温で2時間反応させ1H−NMRで反応が完結しているのを確認した。同じ反応容器に、炭酸水素ナトリウム101.1部、アセトン228.5部、水220部を仕込み、室温で攪拌した。オキソン(ペルオキシ硫酸カリウム複塩)143.7部を4分割して2時間ごとに加えた。室温で一晩反応後、水を加えて2−アセトキシ−1−メトキシプロパンで抽出、水洗後、硫酸マグネシウムで乾燥し、固形分29.4%の不飽和エステル基含有エポキシ樹脂の2−アセトキシ−1−メトキシプロパン溶液を124.6g得た。収率80.3%。
攪拌機、温度計を備えた反応容器に、トリメチロールプロパン2.2部、4−ビニルシクロヘキセン−1−オキサイド3.1部を仕込み70℃で加熱攪拌した。トリメチロールプロパン溶解後、室温まで放冷し、3,4−エポキシシクロへキシルメチルメタクリレート44.0部、4−メトキシフェノール0.04部を仕込み攪拌した。三フッ化ホウ素ジエチルエーテル錯体0.7部と酢酸エチル15.5部を混合し、1時間かけてゆっくり滴下して加えた。室温で2時間反応させ1H−NMRで反応が完結しているのを確認した。同じ反応容器に、炭酸水素ナトリウム101.1部、アセトン228.5部、水220部を仕込み、室温で攪拌した。オキソン(ペルオキシ硫酸カリウム複塩)143.7部を4分割して2時間ごとに加えた。室温で一晩反応後、水を加えて酢酸エチルで抽出、水洗後、硫酸マグネシウムで乾燥し、固形分22.4%の不飽和エステル基含有エポキシ樹脂の酢酸エチル溶液を167.0g得た。収率75.3%。
攪拌機、温度計を備えた反応容器に、エポキシ樹脂(ダイセル化学工業(株)製のEHPE―3150)22.6部、4−メトキシフェノール0.02部、トリメチルベンジルアンモニウムクロライド0.18部、2−アセトキシ−1−メトキシプロパン80部を仕込み110℃で加熱攪拌した。アクリル酸2.2部と2−アセトキシ−1−メトキシプロパン20部を混合し、滴下ロートよりゆっくり滴下して加えた。110℃で4時間攪拌し反応を継続した。室温まで冷却後に水洗し、硫酸マグネシウムで乾燥することで、固形分21.4%の不飽和エポキシエステル樹脂の2−アセトキシ−1−メトキシプロパン溶液を60.1g得た。収率51.9%。
攪拌機、温度計を備えた反応容器に、エポキシ樹脂(ダイセル化学工業(株)製のEHPE―3150)22.6部、4−メトキシフェノール0.02部、トリメチルベンジルアンモニウムクロライド0.18部、酢酸エチル80部を仕込み110℃で加熱攪拌した。アクリル酸22.2部と酢酸エチル20部を混合し、滴下ロートよりゆっくり滴下して加えた。110℃で4時間攪拌し反応を継続した。室温まで冷却後に水洗し、硫酸マグネシウムで乾燥することで、固形分18.4%の不飽和エポキシエステル樹脂の酢酸エチル溶液を63.7g得た。収率40.2%。
GPC(ゲル・パーミエーション・クロマトグラフィー)はTOSOH HLC-8320GPC(TSKgel SUPERHZ 3000、2000、1000)を用いて測定した。
エポキシ当量は、JIS-K-7236(電位差滴定法)に準じて測定した。
酸価は、JIS-K-0072(電位差滴定法)に準じて測定した。
NP−A:ネオペンチルグリコールジアクリレート(共栄社化学製)
4HBA:4−ヒドロキシブチルアクリレート(日本化成製)
PE−3A:ペンタエリスリトールトリアクリレート(共栄社化学製)
Irg651:イルガキュア−651(チバスペシャリティ・ケミカルズ社製)
Irg369:イルガキュア−369(チバスペシャリティ・ケミカルズ社製)
配合例1に示す硬化性材料を、ガラス板上に、ワイヤーバーコーターを用いて膜厚20〜25μmとなるように塗工し、樹脂組成物層を形成した。活性エネルギー線照射装置(東芝社製 高圧水銀灯)で最大照度300mW/cm2、積算光量300mJ/cm2の紫外線を照射して硬化させた。
配合例1に示す硬化性材料を、ガラス板上に、ワイヤーバーコーターを用いて膜厚20〜25μmとなるように塗工し、樹脂組成物層を形成した。次に、150℃のオーブンで1時間加熱して硬化させた。
調製した硬化性材料を室温で5日間保存した後の、硬化性材料の状態を目視で観察した。
○:変化無し
×:増粘あるいはゲル化
硬化物の透明性を目視で評価し、無色透明を○、濁りや着色が見られたものを×とした。
Claims (4)
- 請求項1記載の不飽和エステル基含有エポキシ樹脂を含む硬化性材料。
- さらに、重合開始剤を含む請求項2記載の硬化性材料。
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JPH03285913A (ja) * | 1990-04-02 | 1991-12-17 | Daicel Chem Ind Ltd | ポリエーテル化合物およびエポキシ化合物 |
JPH09263633A (ja) * | 1996-03-28 | 1997-10-07 | Daicel Chem Ind Ltd | 新規ポリエーテル化合物、その製造方法及びそれを用いた硬化性組成物 |
JP2002338879A (ja) * | 2001-03-12 | 2002-11-27 | Honda Motor Co Ltd | カチオン電着浴組成物 |
JP2004250604A (ja) * | 2003-02-20 | 2004-09-09 | Daicel Chem Ind Ltd | シリコーン変性エポキシ樹脂 |
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JPH03285913A (ja) * | 1990-04-02 | 1991-12-17 | Daicel Chem Ind Ltd | ポリエーテル化合物およびエポキシ化合物 |
JPH09263633A (ja) * | 1996-03-28 | 1997-10-07 | Daicel Chem Ind Ltd | 新規ポリエーテル化合物、その製造方法及びそれを用いた硬化性組成物 |
JP2002338879A (ja) * | 2001-03-12 | 2002-11-27 | Honda Motor Co Ltd | カチオン電着浴組成物 |
JP2004250604A (ja) * | 2003-02-20 | 2004-09-09 | Daicel Chem Ind Ltd | シリコーン変性エポキシ樹脂 |
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CN108976714A (zh) * | 2018-07-27 | 2018-12-11 | 华南协同创新研究院 | 一种3d打印用单组份环氧树脂改性光敏树脂组合物及其制备方法 |
CN108976714B (zh) * | 2018-07-27 | 2021-02-19 | 华南协同创新研究院 | 一种3d打印用单组份环氧树脂改性光敏树脂组合物及其制备方法 |
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