JP2011001483A - エポキシ樹脂組成物、その硬化物、及び半導体装置 - Google Patents
エポキシ樹脂組成物、その硬化物、及び半導体装置 Download PDFInfo
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- JP2011001483A JP2011001483A JP2009146332A JP2009146332A JP2011001483A JP 2011001483 A JP2011001483 A JP 2011001483A JP 2009146332 A JP2009146332 A JP 2009146332A JP 2009146332 A JP2009146332 A JP 2009146332A JP 2011001483 A JP2011001483 A JP 2011001483A
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- Prior art keywords
- epoxy resin
- group
- resin composition
- aromatic hydrocarbon
- hydrocarbon group
- Prior art date
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- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 222
- 239000000203 mixture Substances 0.000 title claims abstract description 90
- 239000004065 semiconductor Substances 0.000 title claims abstract description 26
- -1 glycidyloxy group Chemical group 0.000 claims abstract description 45
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 28
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 26
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 25
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 19
- 239000004593 Epoxy Substances 0.000 claims abstract description 17
- 125000001118 alkylidene group Chemical group 0.000 claims abstract description 13
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 claims abstract description 13
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 4
- 239000003063 flame retardant Substances 0.000 claims description 44
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
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- 150000002367 halogens Chemical class 0.000 claims description 17
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- 125000003118 aryl group Chemical group 0.000 claims description 15
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- 229910052751 metal Inorganic materials 0.000 abstract description 20
- 239000002184 metal Substances 0.000 abstract description 20
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- 238000000034 method Methods 0.000 description 47
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 31
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- 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 20
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 14
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- 238000010438 heat treatment Methods 0.000 description 11
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- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 7
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 229910000679 solder Inorganic materials 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- NQMUGNMMFTYOHK-UHFFFAOYSA-N 1-methoxynaphthalene Chemical compound C1=CC=C2C(OC)=CC=CC2=C1 NQMUGNMMFTYOHK-UHFFFAOYSA-N 0.000 description 5
- LUZDYPLAQQGJEA-UHFFFAOYSA-N 2-Methoxynaphthalene Chemical compound C1=CC=CC2=CC(OC)=CC=C21 LUZDYPLAQQGJEA-UHFFFAOYSA-N 0.000 description 5
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- 239000002904 solvent Substances 0.000 description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
Abstract
【解決手段】主剤エポキシ樹脂成分として、グリシジルオキシ基含有芳香族炭化水素基(E)、アルコキシ基含有縮合多環式芳香族炭化水素基(B)、並びに、メチレン基、アルキリデン基、及び芳香族炭化水素構造含有メチレン基から選択される2価の炭化水素基(X)の各構造部位を有しており、かつ、前記(E)及び前記(B)が、前記炭化水素基(X)を介して結合した構造を分子構造内に有するエポキシ樹脂(a1)、及び、ビスフェノール型エポキシ樹脂及びビフェノール型エポキシ樹脂からなる群から選択され、かつ、エポキシ当量が250g/eq〜700g/eqの範囲にある2官能エポキシ樹脂(a2)を併用する。
【選択図】なし
Description
前記エポキシ樹脂組成物を封止材料に代表されるエレクトロニクス材料分野に用いる場合、これまで硬化物に難燃性を付与するために臭素等のハロゲン系難燃剤がアンチモン化合物とともに配合されている。しかし、近年の環境・安全への取り組みのなかで、ダイオキシン発生が懸念されるハロゲン系難燃剤を用いず、且つ発ガン性が疑われているアンチモン化合物を用いない環境・安全対応型の難燃化方法の開発が強く要求されている。また、半導体封止材料の非ハロゲン化は半導体装置の高温放置信頼性の改良にも大きく貢献する技術であり、市場における期待は高い。
かかる要求特性に応える電子部品封止材料としては、例えば、ヒドロキシ基含有芳香族化合物とアルコキシ基含有芳香族化合物とカルボニル基含有化合物とを反応させたフェノール樹脂をエピハロヒドリンと反応させたエポキシ樹脂が知られている(下記、特許文献1参照)。
しかしながら、特許文献1において開示されているエポキシ樹脂は、ある程度の難燃性は達成しているものの、近年要求の高い、より高度な難燃性能を満足することはできず、また、リードフレーム等の金属への接着性が十分なものではなかった。
この点につき詳述するに、例えば半導体封止材料分野では、鉛フリー半田への移行によりリフロー処理温度が高温化するに至り、耐ハンダクラック性(リフロー性)の向上が求められており、その手段として溶融シリカ粉末等の無機充填剤を高充填化により低吸湿化する手段が用いられているが、この場合、樹脂とリードフレーム(Cu、Ag、PPFなど)に代表される金属との接着性が低くなり、リードフレームと封止材との間で剥離が生じ易いという問題を有していた。従って、鉛フリー半田に対応する電子部品封止材材料としてリードフレームとの接着性に優れた材料が求められていた。
グリシジルオキシ基含有芳香族炭化水素基(E)、アルコキシ基含有縮合多環式芳香族炭化水素基(B)、並びに、
メチレン基、アルキリデン基、及び芳香族炭化水素構造含有メチレン基から選択される2価の炭化水素基(X)の各構造部位を有しており、かつ、前記グリシジルオキシ基含有芳香族炭化水素基(E)及び前記アルコキシ基含有縮合多環式芳香族炭化水素基(B)が、前記メチレン基、アルキリデン基、及び芳香族炭化水素構造含有メチレン基から選択される2価の炭化水素基(X)を介して結合した構造を分子構造内に有するエポキシ樹脂(a1)と、ビスフェノール型エポキシ樹脂及びビフェノール型エポキシ樹脂からなる群から選択され、かつ、エポキシ当量が250g/eq〜700g/eqの2官能エポキシ樹脂(a2)とを併用することにより、非ハロゲン系であり乍ら、その硬化物が極めて高い難燃性を発現すると共に金属との密着性に優れることを見出し、本発明を完成させるに至った。
前記エポキシ樹脂(A)として、
グリシジルオキシ基含有芳香族炭化水素基(E)、
アルコキシ基含有縮合多環式芳香族炭化水素基(B)、並びに、
メチレン基、アルキリデン基、及び芳香族炭化水素構造含有メチレン基から選択される2価の炭化水素基(X)の各構造部位を有しており、かつ、
前記グリシジルオキシ基含有芳香族炭化水素基(E)及び前記アルコキシ基含有縮合多環式芳香族炭化水素基(B)が、前記メチレン基、アルキリデン基、及び芳香族炭化水素構造含有メチレン基から選択される2価の炭化水素基(X)を介して結合した構造を分子構造内に有するエポキシ樹脂(a1)、及び、
ビスフェノール型エポキシ樹脂及びビフェノール型エポキシ樹脂からなる群から選択され、かつ、エポキシ当量が250g/eq〜700g/eqの範囲にある2官能エポキシ樹脂(a2)
を併用することを特徴とするエポキシ樹脂組成物に関する。
本発明で用いられるエポキシ樹脂(A)の一成分であるエポキシ樹脂(a1)は、グリシジルオキシ基含有芳香族炭化水素基(E)、アルコキシ基含有縮合多環式芳香族炭化水素基(B)、並びに、メチレン基、アルキリデン基、及び芳香族炭化水素構造含有メチレン基から選択される2価の炭化水素基(X)の各構造部位を有しており、かつ、前記グリシジルオキシ基含有芳香族炭化水素基(E)及び前記アルコキシ基含有縮合多環式芳香族炭化水素基(B)が、前記メチレン基、アルキリデン基、及び芳香族炭化水素構造含有メチレン基から選択される2価の炭化水素基(X)を介して結合した構造を分子構造内に有するエポキシ樹脂で表されるものである。本発明ではかかるエポキシ樹脂(a1)を用いることから硬化物に優れた難燃性を付与することができる。
1,4−ジメトキシナフタレン、1−t−ブトキシナフタレン、1−メトキシアントラセン、等が挙げられる。
方法2):アルコキシ基含有縮合多環式芳香族化合物(b)1モルに対して、0.05〜30モル、好ましくは2〜30モルのカルボニル基含有化合物(x)を反応させた後に、ヒドロキシ基含有芳香族系化合物(p)を仕込んで反応させる方法。
方法3):ヒドロキシ基含有芳香族系化合物(p)とアルコキシ基含有縮合多環式芳香族化合物(b)とを予め混合しておき、ここにカルボニル基含有化合物(x)を連続的乃至断続的に系内に加えることによって、反応を行う方法。
なお、上記したビスフェノールFは、多核体を0.1〜20質量%の範囲で含有していてもよい。
方法3):前記ビスフェノール及び前記ビフェノール類から選択される2官能フェノールとエピハロヒドリンとを、該2官能フェノールのフェノール性水酸基に対しエピハロヒドリンが過剰となる割合で反応させて低分子量エポキシ樹脂を得、次いで、得られた低分子量エポキシ樹脂と前記2官能フェノール化合物とを、低分子量エポキシ樹脂のエポキシ1当量に対して前記2官能フェノール化合物の水酸基当量が0.05〜0.35当量となる割合で重付加反応させる方法。
方法4):エピハロヒドリンと前記2官能フェノール化合物とをエピクロルヒドリン1.0molに対してフェノール性水酸基0.9〜2.0当量となる割合で反応させてエポキシ樹脂を得る方法。
次いで、低分子量エポキシ樹脂と前記2官能フェノール化合物との反応は、水酸化ナトリウム、水酸化カリウム等のアルカリ金属水酸化物、トリエチルアミン、ベンジルジメチルアミン等の第三級アミン、テトラメチルアンモニウムクロライド等の第4級アンモニウム塩、イミダゾール化合物、トリフェニルホスフィン等の触媒を用い反応さて得ることができる。
フェノ−ル系化合物などのエポキシ樹脂用硬化剤が挙げられる。
フェノール性水酸基含有芳香族炭化水素基(P)、
アルコキシ基含有縮合多環式芳香族炭化水素基(B)、並びに、
メチレン基、アルキリデン基、及び芳香族炭化水素構造含有メチレン基から選択される2価の炭化水素基(X)
の各構造部位を有しており、かつ、前記フェノール性水酸基含有芳香族炭化水素基(P)及び前記アルコキシ基含有縮合多環式芳香族炭化水素基(B)が、前記メチレン基、アルキリデン基、及び芳香族炭化水素構造含有メチレン基から選択される2価の炭化水素基(X)を介して結合した構造を分子構造内に有する
のフェノール樹脂が挙げられる。
(式中、X2は置換基を有していてもよい芳香環であり、Ar2はフェニル基、ビフェニル基、ナフチル基、若しくはこれらの芳香核にアルキル基を有する構造部位でありnは1〜4である。)で表されるフェノール樹脂が挙げられる。
これらの硬化剤はそれぞれ単独で用いてもよく、また、2種以上併用してもよい。
その充填率は、用途に応じ適宜選択すればよいが、半導体封止材用途では、難燃性を考慮して、高い方が好ましく、エポキシ樹脂組成物の全体量に対して65〜95質量%、より好ましくは80〜95質量%の範囲であることが特に好ましい。また導電ペーストなどの用途に使用する場合は、銀粉や銅粉等の導電性充填剤を用いることができる。
箔上で当該樹脂組成物を半硬化させた樹脂付き銅箔を、回路を形成した配線基板上に、170〜250℃で加熱圧着することで、粗化面を形成、メッキ処理の工程を省き、ビルドアップ基板を作製することも可能である。
・中間点ガラス転移温度:
以下の条件にて測定したDSC曲線において、JIS K7121に準拠し各ベースラインの延長した直線から縦軸方向に等距離にある直線と、ガラス転移の段階状変化部分の曲線とが交わる点の温度とした。
装置 ;メトラー・トレド株式会社製 DSC1
サンプル量 ;約5mg
測定温度範囲;−30℃〜100℃
温度条件 ;3℃/min.
・抽出水塩素イオン;
直径58mm、深さ33mmの加圧可能な容器に、サンプル5gと蒸留水50gを入れて160℃で20時間加熱した。その後、室温まで冷却した後、上澄み液の塩素イオンを測定した。
温度計、冷却管、分留管、窒素ガス導入管、撹拌器を取り付けたフラスコに、o−クレゾール432.4g(4.00モル)と2−メトキシナフタレン158.2g(1.00モル)と41質量%ホルムアルデヒド水溶液179.3g(ホルムアルデヒド2.45モル)を仕込み、シュウ酸9.0gを加えて、100℃まで昇温し100℃で3時間反応させた。ついで、水を分留管で捕集しながら41質量%ホルムアルデヒド水溶液73.2g(ホルムアルデヒド1.00モル)を1時間かけて滴下した。滴下終了後、150℃まで1時間で昇温し、更に150℃で2時間反応させた。反応終了後、更にメチルイソブチルケトン1500gを加え、分液ロートに移し水洗した。次いで洗浄水が中性を示すまで水洗後、有機層から未反応のo−クレゾールと2−メトキシナフタレン、及びメチルイソブチルケトンを加熱減圧下に除去しフェノール樹脂を得た。得られたフェノール樹脂の水酸基当量は164g/eq.であった。
温度計、滴下ロート、冷却管、撹拌機を取り付けたフラスコに、窒素ガスパージを施しながら、ビスフェノールF(DIC株式会社製「DIC−BPF」)142.8g(水酸基1.43当量)、エピクロルヒドリン92.5g(1.0モル)、n−ブタノール40g仕込み溶解させた。その後、20%水酸化ナトリウム水溶液240gを3時間かけて滴下し、更に同温度に2時間の間保持して反応を続行させてからメチルイソブチルケトン250gを加えて80℃に昇温した後に水層を除去した。その後、洗浄液のPHが中性となるまで水150gで水洗を3回繰り返した。共沸蒸留により水を除去、ろ過し、更にメチルイソブチルケトンを留去してエポキシ樹脂(E−2)を得た。得られたエポキシ樹脂の溶融粘度(測定法:ICI粘度計法、測定温度:150℃)は2.6dPa・s、エポキシ当量は475g/eqであった。
合成例2において、ビスフェノールF(DIC株式会社製「DIC−BPF」)の代わりに3,3’,5,5’−テトラメチル−4,4’−ビフェノール151.3g(水酸基1.25当量)、エピクロルヒドリン92.5g(1.0モル)を用いた以外は、合成例2と同様にしてエポキシ樹脂(E−3)を得た。得られたエポキシ樹脂の溶融粘度(測定法:ICI粘度計法、測定温度:150℃)は2.0dPa・s、エポキシ当量は350g/eqであった。
温度計、滴下ロート、冷却管、撹拌機を取り付けたフラスコに、窒素ガスパージを施しながら、ビスフェノールA型液状エポキシ樹脂(DIC株式会社製「エピクロン850−S」エポキシ当量188g/eq)188g(エポキシ基1当量)、ビスフェノールA19g(0.083モル)、トリフェニルホスフィン0.04gを仕込み140℃まで4時間で昇温した。その後140℃で5時間反応させてエポキシ樹脂(E−5)を得た。得られたエポキシ樹脂の溶融粘度(測定法:ICI粘度計法、測定温度:150℃)は0.2dPa・s、エポキシ当量は250g/eq.であった。
合成例1〜5で得られたエポキシ樹脂及びビスフェノールA型固形エポキシ樹脂(DIC株式会社製「エピクロン 1055」エポキシ当量475g/eq.、軟化点69℃)を表1の記載した配合で混合し(混合温度:130℃)実施例に用いるエポキシ樹脂を作成した。
表2〜3に示す各種の素材を用い、2本ロールを用いて100℃の温度で10分間溶融混練して目的の組成物を得た。得られたエポキシ樹脂組成物について、下記方法によりゲルタイムを測定し、硬化性を試験した。また、これを180℃で10分間プレス成形し、その後180℃で5時間さらに硬化せしめた後に、DMA測定及びUL−94V試験用の試験片を作成し、下記方法により硬化物の物性を評価した。密着性は前記プレス成形する際にエポキシ樹脂組成物の片面に銅箔(古河サーキットホイル株式会社製。厚さ35μm、GTS−MP処理したもののシャイン面を樹脂組成物との接着面として使用)をおいて得られたものを180℃で5時間さらに硬化せしめたものから試験片を作成した。
得られた硬化物の評価結果を表4に示す。
・ガラス転移温度:粘弾性測定装置(レオメトリック社製 固体粘弾性測定装置「RSAII」、二重カレンチレバー法;周波数1Hz、昇温速度3℃/分)を用いて測定した。
熱時弾性率:粘弾性測定装置(レオメトリック社製 固体粘弾性測定装置「RSAII」、二重カレンチレバー法;周波数1Hz、昇温速度3℃/分)を用いて測定し、得られたチャートの貯蔵弾性率を測定した。
・密着性:
幅1.0mmの試験片を用い、50mm/分の速度でピール強度を測定した。
・難燃性:
UL−94試験法に準拠し、厚さ1.6mmの試験片5本を用いて、燃焼試験を行った。
Claims (10)
- エポキシ樹脂(A)と硬化剤(B)を必須成分とするエポキシ樹脂組成物であって、
前記エポキシ樹脂(A)として、
グリシジルオキシ基含有芳香族炭化水素基(E)、
アルコキシ基含有縮合多環式芳香族炭化水素基(B)、並びに、
メチレン基、アルキリデン基、及び芳香族炭化水素構造含有メチレン基から選択される2価の炭化水素基(X)の各構造部位を有しており、かつ、
前記グリシジルオキシ基含有芳香族炭化水素基(E)及び前記アルコキシ基含有縮合多環式芳香族炭化水素基(B)が、前記メチレン基、アルキリデン基、及び芳香族炭化水素構造含有メチレン基から選択される2価の炭化水素基(X)を介して結合した構造を分子構造内に有するエポキシ樹脂(a1)、及び、
ビスフェノール型エポキシ樹脂及びビフェノール型エポキシ樹脂からなる群から選択され、かつ、エポキシ当量が250g/eq〜700g/eqの範囲にある2官能エポキシ樹脂(a2)
を併用することを特徴とするエポキシ樹脂組成物。 - 前記エポキシ樹脂(A)中の前記エポキシ樹脂(a1)と前記2官能エポキシ樹脂(a2)の質量比率[(a1)/(a2)]が、95/5〜60/40となる範囲のものである請求項1記載のエポキシ樹脂組成物
- 前記エポキシ樹脂(A)が、前記エポキシ樹脂(a1)及び前記2官能エポキシ樹脂(a2)の混合物であって、該混合物を示差走査熱量測定(DSC)により−30℃から100℃まで毎分3℃の速度で昇温して測定した際の中間点ガラス転移温度が5〜30℃の範囲である請求項1記載のエポキシ樹脂組成物。
- 前記エポキシ樹脂(A)が、前記エポキシ樹脂(a1)及び前記2官能エポキシ樹脂(a2)の混合物であって、該混合物の150℃におけるICI粘度計における溶融粘度が、0.1〜3.0dPa・sの範囲である請求項1記載のエポキシ樹脂組成物。
- 前記硬化剤(B)が、ビスアラルキルを結節基として水酸基含有芳香族構造が連結された構造を含有するヒドロキシ芳香族化合物である請求項1〜5の何れか1つに記載のエポキシ樹脂組成物。
- 更に、硬化促進剤を含有する請求項1記載のエポキシ樹脂組成物。
- 更に、無機質充填剤を含有する請求項1記載のエポキシ樹脂組成物。
- リン系難燃剤、窒素系難燃剤、シリコーン系難燃剤、無機系難燃剤、有機金属系難燃剤からなる群から選択される1種以上の非ハロゲン系難燃剤(C)を含有する請求項1記載のエポキシ樹脂組成物。
- 請求項1〜8のいずれか1つに記載のエポキシ樹脂組成物を硬化させてなる硬化物。
- 請求項1〜8のいずれか1つに記載のエポキシ樹脂組成物を用い、半導体チップ及びリードフレームを封止してなる半導体装置。
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US9896535B2 (en) | 2011-08-25 | 2018-02-20 | Korea Institute Of Industrial Technology | Epoxy compound having alkoxysilyl group, method of preparing the same, composition and cured product comprising the same, and uses thereof |
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US11840601B2 (en) | 2019-11-15 | 2023-12-12 | Korea Institute Of Industrial Technology | Composition of alkoxysilyl-functionalized epoxy resin and composite thereof |
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