JP2014513195A - 高い熱安定性とじん性を示すエポキシ樹脂 - Google Patents
高い熱安定性とじん性を示すエポキシ樹脂 Download PDFInfo
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- JP2014513195A JP2014513195A JP2014510370A JP2014510370A JP2014513195A JP 2014513195 A JP2014513195 A JP 2014513195A JP 2014510370 A JP2014510370 A JP 2014510370A JP 2014510370 A JP2014510370 A JP 2014510370A JP 2014513195 A JP2014513195 A JP 2014513195A
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- epoxy resin
- resin composition
- epoxy
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- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 93
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 71
- 239000000203 mixture Substances 0.000 claims abstract description 77
- 229920005989 resin Polymers 0.000 claims abstract description 38
- 239000011347 resin Substances 0.000 claims abstract description 38
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- 239000012744 reinforcing agent Substances 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 30
- 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 claims description 28
- 239000004593 Epoxy Substances 0.000 claims description 27
- -1 bisphenol compound Chemical class 0.000 claims description 23
- 239000004970 Chain extender Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 239000012745 toughening agent Substances 0.000 claims description 15
- 229930185605 Bisphenol Natural products 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 239000000758 substrate Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000003700 epoxy group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
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- 125000000962 organic group Chemical group 0.000 claims description 5
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
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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 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
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- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims 2
- 125000002723 alicyclic group Chemical group 0.000 claims 1
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 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 6
- 239000000463 material Substances 0.000 description 6
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- 229920000058 polyacrylate Polymers 0.000 description 6
- 239000005060 rubber Substances 0.000 description 6
- DNDWXJDUTDZBNV-UHFFFAOYSA-N 1-benzofuran-2,3-diol Chemical compound C1=CC=C2C(O)=C(O)OC2=C1 DNDWXJDUTDZBNV-UHFFFAOYSA-N 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 229920000193 polymethacrylate Polymers 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- 229920013646 Hycar Polymers 0.000 description 3
- 229920002633 Kraton (polymer) Polymers 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000001588 bifunctional effect 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
- 150000004985 diamines Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
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- 150000003254 radicals Chemical class 0.000 description 3
- 239000011342 resin composition Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- 229920009204 Methacrylate-butadiene-styrene Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical class C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
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- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical class OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
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- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
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- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
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Classifications
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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- C08G59/226—Mixtures of di-epoxy compounds
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Abstract
Description
(a)ポリエポキシド樹脂、
(b)一般式(III)または(V):
OH−A−OH (III)
R2O−A−OR2 (V)
[式中、
Aは、式(IV)
R2は、炭素原子数が1から6のエポキシ官能アルキル基である]
で表される少なくとも1種の化合物を含有して成る鎖延長剤、
(c)強化剤、
(d)硬化剤、および場合により
(e)ビスフェノール化合物、
を含有して成る。
質的に成る”が本明細書に現れる場合、それは実現可能性に必須ではないもの以外は引き続くいずれかの記述の範囲から他の如何なる成分も段階も手順も排除するものであり、そして用語“から成る”を用いる場合、それは具体的に詳しく説明することも挙げることもなかった如何なる成分も段階も手順も排除するものである。用語“または”は、特に明記しない限り、個々に挙げた員ばかりでなく任意組み合わせの員を指すものである。
応性エポキシ基の約5%−90%、好適には約9%−70%がベンゾフランジオール成分によってもたらされる活性ヒドロキシ基と反応するような量にする一方で、他の態様では、ベンゾフランジエポキシド成分の使用量を結果としてもたらされる樹脂の約2%−78%(重量)、好適には約4%−60%(重量)がベンゾフラン単位を含有するような量にする。硬化剤の使用量はそれが有する官能基の濃度および分子量に依存する。いくつかの態様では、硬化剤の使用量をエポキシ樹脂組成物内に存在する実質的な量の残存反応性エポキシ基と反応するに充分な量にする。本明細書では用語“実質的な量”を結果として所望のガラス転移温度とじん性を示す硬化エポキシ樹脂がもたらされるに充分な架橋を生じさせるに充分な量を指す目的で用いる。
で表されるエポキシ樹脂である。本明細書で用いる如き“ヒドロカルビル”は炭化水素基を指し、それには、これらに限定するものでないが、アリール、アルキル、シクロアルキ
ル、アルケニル、シクロアルケニル、シクロアルカジエニル、アルキニル、アラルキル、アラルケニル、アラルキニルなどが含まれ、それらにはそれらのあらゆる置換、非置換、分枝、直鎖、ヘテロ原子置換誘導体が含まれる。同様に、用語“ヒドロカルビルオキシ”は、ヒドロカルビル基とこれが結合している物との間に酸素結合を有するヒドロカルビル基を指す。
OH−A−OH (III)
で表される化合物が含まれ、ここで、Aは式(IV)
R2O−A−OR2 (V)
で表される化合物であり、ここで、Aはこの上で定義した通りであり、そしてR2は炭素原子数が1から6のエポキシ官能アルキル基である。好適な態様として、各R2は2,3−エポキシプロピル基である。この態様では、ジヒドロキシ化合物の反応によってではなくジエポキシ化合物の反応によってベンゾフラン単位がポリエポキシド樹脂の中に組み込まれる。
ン、ジクロロスチレンおよびエチルクロロスチレンであり得る。
て強化される本開示の特徴である。
で表される。
度より低い温度で実施する。強化後に温度を上昇させて硬化を起こさせる。積層後の部品にしばしば独立後硬化を更により高い温度のオーブン内で受けさせる。
a)(i)ポリエポキシド樹脂、(ii)上述した如きベンゾフランジオール成分、ベンゾフランジエポキシド成分またはこれらの混合物、(iii)強化剤および(iv)硬化剤を含有して成るエポキシ樹脂組成物を準備し、
b)前記エポキシ樹脂組成物を1つ以上の前記基質の少なくとも1つの表面に塗布し、そして
c)一緒に結合させるべき前記基質の前記表面を一致するように噛み合わせて前記組成物を硬化させることでそれらの間に結合を生じさせる、
ことを包含する。
ーラーコーティングなどで硬化剤を塗布する前、塗布した後または同時に所望の厚みになるように塗布してもよい。塗布後の組成物を周囲条件および/または熱をかけて硬化させる。それらの表面および間に位置する本エポキシ樹脂組成物を本組成物が前記表面を結合させるに充分なほど硬化するまで噛み合わせ状態に維持する。本組成物を塗布することが可能な基質の例には、これらに限定するものでないが、鋼、亜鉛メッキ鋼、アルミニウム、銅、真鍮、木、ガラス、紙、複合材料、セラミック、プラスチックおよび高分子材料、例えばポリエステル、ポリアミド、ポリウレタン、ポリ塩化ビニル、ポリカーボネート、ABSプラスチックなどおよびプレキシガラスが含まれる。
Claims (10)
- 前記ポリエポキシド樹脂がエポキシ基を約2個有する1種以上の脂肪族、脂環式または芳香族が基になったエポキシ化合物を含有して成る請求項1記載のエポキシ樹脂組成物。
- 前記エポキシ化合物が構造式(IA)または(IB)または(IC):
で表されるエポキシ樹脂である請求項2記載のエポキシ樹脂組成物。 - A1がフェニル、ジフェニルメタン、ビフェニル、メタン基が1または2個のC1-C4アルキル基で置換されているジフェニルメタン、ジフェニルケトンまたはジフェニルスルホンである請求項1記載のエポキシ樹脂組成物。
- 前記強化剤がカルボキシル化もしくはアミン末端アクリロニトリル/ブタジエンエラストマーである請求項1記載のエポキシ樹脂組成物。
- 前記鎖延長剤が一般式(V):
R2O−A−OR2 (V)
[式中、AおよびR2は請求項1で定義した通りである]
で表される化合物である請求項1記載のエポキシ樹脂組成物。 - 更にビスフェノールA、ビスフェノールF、ビスフェノールR、ビスフェノールSおよびこれらの混合物から選択されるビスフェノール化合物も含有して成る請求項7記載のエポキシ樹脂組成物。
- エポキシ樹脂組成物であって、ベンゾフランジオールおよび/またはベンゾフランジエポキシド成分および強化剤の存在下で式(VI)
で表されるポリエポキシド樹脂を含有して成るエポキシ樹脂組成物。 - 少なくとも2つの基質を一緒に結合させる方法であって、
a)(i)ポリエポキシド樹脂、(ii)一般式(III)または(V):
OH−A−OH (III)
R2O−A−OR2 (V)
[式中、Aは、式(IV)
R2は、炭素原子数が1から6のエポキシ官能アルキル基である]
で表される少なくとも1種の化合物を含有して成る鎖延長剤、(iii)強化剤および(iv)硬化剤、
を含有して成るエポキシ樹脂組成物を準備し、
b)前記エポキシ樹脂組成物を1つ以上の前記基質の少なくとも1つの表面に塗布し、そして
c)一緒に結合させるべき前記基質の前記表面を一致するように噛み合わせて前記組成物を硬化させることでそれらの間に結合を生じさせる、
ことを含んで成る方法。
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US201161485902P | 2011-05-13 | 2011-05-13 | |
US61/485,902 | 2011-05-13 | ||
PCT/US2012/036421 WO2012158363A1 (en) | 2011-05-13 | 2012-05-04 | Epoxy resins with high thermal stability and toughness |
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US (1) | US9051498B2 (ja) |
EP (1) | EP2751160B1 (ja) |
JP (1) | JP2014513195A (ja) |
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CN (1) | CN103534289B (ja) |
AU (1) | AU2012256282B2 (ja) |
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CA (1) | CA2835204A1 (ja) |
ES (1) | ES2612236T3 (ja) |
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US9890237B2 (en) * | 2013-06-26 | 2018-02-13 | Dic Corporation | Epoxy compound, epoxy resin, curable compound, cured product thereof, semiconductor sealing material, and printed circuit board |
US20180148596A1 (en) | 2015-05-20 | 2018-05-31 | 3M Innovative Properties Company | High temperature stable, one-part, curable thermoset compositions |
WO2017106596A1 (en) | 2015-12-18 | 2017-06-22 | 3M Innovative Properties Company | Curable epoxy compositions and methods for accelerating the curing of epoxy compositions |
CN107502261B (zh) * | 2017-09-14 | 2020-07-14 | 广州欣凯化工科技有限公司 | 一种用于木制品的耐高温抗冻树脂胶 |
FR3073223B1 (fr) * | 2017-11-07 | 2019-11-15 | Arianegroup Sas | Composes biphenyles pluriepoxydes, preparation et utilisations |
KR102566321B1 (ko) * | 2021-07-26 | 2023-08-14 | 한국화학연구원 | 산 무수물기반 에폭시 화합물, 이를 포함하는 에폭시 수지 이액형 조성물 및 이로부터 제조된 경화물 |
CN116410714A (zh) * | 2021-12-30 | 2023-07-11 | 天津中油渤星工程科技有限公司 | 一种树脂胶凝材料及其制备方法 |
CN116144165B (zh) * | 2022-12-27 | 2024-04-02 | 四川大学 | 可回收、可修复的热固性聚氨酯改性沥青材料及其制法 |
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- 2012-05-04 CA CA2835204A patent/CA2835204A1/en not_active Abandoned
- 2012-05-04 EP EP12785700.1A patent/EP2751160B1/en active Active
- 2012-05-04 CN CN201280023141.4A patent/CN103534289B/zh active Active
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- 2012-05-04 ES ES12785700.1T patent/ES2612236T3/es active Active
- 2012-05-04 WO PCT/US2012/036421 patent/WO2012158363A1/en active Application Filing
- 2012-05-10 TW TW101116720A patent/TW201302832A/zh unknown
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JPS51149263A (en) * | 1975-06-02 | 1976-12-22 | Eastman Kodak Co | Production of dihydrobenzofrandiols from quinones and carbonyl compound |
JPH06199863A (ja) * | 1992-10-29 | 1994-07-19 | Ciba Geigy Ag | 多環式フェノールから誘導されたエポキシ樹脂 |
JP2004263021A (ja) * | 2003-02-28 | 2004-09-24 | Sumitomo Chem Co Ltd | ポリエーテル樹脂および絶縁膜形成用塗布液 |
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AU2012256282B2 (en) | 2015-12-17 |
EP2751160A4 (en) | 2015-04-22 |
AU2012256282A1 (en) | 2013-10-31 |
EP2751160A1 (en) | 2014-07-09 |
ES2612236T3 (es) | 2017-05-12 |
CA2835204A1 (en) | 2012-11-22 |
KR20140043752A (ko) | 2014-04-10 |
CN103534289B (zh) | 2016-08-17 |
WO2012158363A1 (en) | 2012-11-22 |
BR112013028011A2 (pt) | 2019-09-24 |
EP2751160B1 (en) | 2016-09-28 |
CN103534289A (zh) | 2014-01-22 |
US9051498B2 (en) | 2015-06-09 |
TW201302832A (zh) | 2013-01-16 |
US20140069583A1 (en) | 2014-03-13 |
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