JP5597700B2 - ポリマーおよび表面改質六方晶窒化ホウ素粒子を含む流延組成物から製造されるフィルム - Google Patents
ポリマーおよび表面改質六方晶窒化ホウ素粒子を含む流延組成物から製造されるフィルム Download PDFInfo
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Description
本出願は、本出願と同日に出願された共同所有の出願[代理人整理番号第CL4388号、CL4658号およびCL4660号]と関連するものである。
にない場合に本質的に不安定である。不安定化事象が万一発生した場合、アルコールなどの可燃性液体の存在は、火災に対し望ましくない燃料を追加するものと考えられる。
硬化されたフィルムのガラス転移温度(Tg)と面内熱膨張係数(CTE)を、IPC試験方法第2.4.24.5にしたがってThermal Mechanical Analyzerを用いて決定した。CTEは、フィルムの平面内で単一方向で決定した。フィルムのガラス転移、弾性率および損失弾性率を、IPC試験方法第2.4.24.4にしたがって、Dynamic Mechanical Analyzerを用いて決定した。
伝導率=拡散係数×Cp×嵩密度
フィルムの比熱(Cp)を、標準的方法を用いるサファイア標準に対し示差走査熱量計(DSC)を使用して測定した。厚みtと嵩密度ρ(w/{πr2・t})の値は、室温測定に基づいている。
100mlの脱イオン水と57mlの0.5M塩酸中に室温で8.0gのパラフェニレンジアミンを溶解させた。50mlの脱イオン水中に溶解させた亜硝酸ナトリウム5.1gを溶液に添加して、対応するジアゾニウムクロリドを作った。ジアゾニウム塩溶液を、200mlのメタノールおよび800mlの水中に分散させた25gのhBN(NX1 grade、Momentive Performance Materials、Strongsville、USA)を含む分散に添加した。鉄粉末(325メッシュ)6.0gグラムを分散に添加し、室温で撹拌した。5分後に、この分散に250mlの0.5M塩酸を添加し、さらに30分(min)間撹拌した。分散を濾過し、水、アンモニア溶液(1リットルの水中にアンモニア溶液25cc)そして次にメタノールで洗浄した。生成物を、真空オーブン内において一晩100℃で乾燥させ、乾燥SMhBNを生成した。
実施例1の手順にしたがったものの、パラフェニレンジアミン(PPD)の量は変えられた。亜硝酸ナトリウム、塩酸および鉄の量は、モルベースでパラフェニレンジアミンと比例して変更した。TGAから測定した重量損失データ(250〜600℃)をhBN表面上のアミノフェニルグラフトの量として取上げた。結果は表2に示されている。
異なるグレードのhBNを表面改質するために実施例1の手順を使用した。室温で50mlの脱イオン水と28.5mlの0.5M塩酸中に4.0gのPPDを溶解させた。50mlの脱イオン水中に溶解させた亜硝酸ナトリウム2.55gをこの溶液に添加して対応するジアゾニウムクロリドを作った。このジアゾニウム塩溶液を、100mlのメタノールおよび400mlの水中の25gの1グレードの六方晶窒化ホウ素(NX1、PT120 & PT620、Momentive Performance Materials、Strongsville、USA)を各々含む分散に添加した。鉄粉末(325メッシュ)3.0gグラムを各分散に添加し、室温で撹拌した。5分後に、各々の分散に125mlの0.5M塩酸を添加し、さらに30分間撹拌した。各分散を濾過し、水、1リットルの水とアンモニア溶液25ccからなるアンモニア溶液、その後メタノールで洗浄し真空オーブン内において100℃で乾燥させた。表面官能基の量を熱重量分析により決定した。結果は表3に示されている。
実施例1に報告されているこの同じ手順を、hBN表面上でヒドロキシファニルグラフトを行なうためにも使用した。PPDを同量のパラアミノフェノールで置換した。反応後、TGAにより、このように製造したSMhBNがその全重量に基づいて約0.51重量%のヒドロキシフェニル基を含んでいることが示された。SMhBNのToF−SIMS分析は、m/z93および107で陽イオンピークを示した。93での陽イオンピークは、hBNの表面上の−C6H4−OH基を確認した。107でのピークは、−N−C6H4−OHに対応し、ヒドロキシフェニル基が共有結合を通してhBN内のN原子に付着されていることを確認している。
窒素雰囲気下において室温でジメチルアセトアミド(DMAc)溶媒中の0.8モルの4.4’−オキシ−3,4,3’,4’−ジフタル無水物(ODPA)と0.2モルのピロメリト酸二無水物(PMDA)を1.0モルの1,3−(4−アミノフェノキシ)ベンゼン(134APB)と反応させることにより、ポリアミド酸溶液を形成した。このように製造したポリアミド酸溶液の粘度は、1.40s−1せん断速度で8500cpであった。固形分含有量は19.5重量%であった。
40.0gの上述のポリアミド酸溶液を、受取ったままのhBN7.8gと混合し、分散を30分間室温で撹拌した。Brookfield Model DV−II+Viscometerを用いて、分散の粘度を測定した。結果は表4に示されている。この組成は、50重量%の樹脂と50重量%のhBNとを含む硬化フィルムの組成に対応していた。
同量のポリアミド酸、実施例1のSMhBNを用いて比較例Bの分散と類似した分散を作り、粘度を測定した。データを表4にまとめる。
実施例1の通りに製造した30gのSMhBNを機械的撹拌器を用いて60gのDMAcと組合せ、分散を形成した。SMhBN分散に実施例10のポリアミド酸溶液51.3gを添加し、75%の速度で4分間Silverson Homogenizerを用いて十分に混合して、SMhBN/ポリアミド酸濃縮物またはマスターバッチを形成した。
機械的撹拌器を用いて、DMAc60gと受取ったままのhBN(NX1グレード)30gを混合することによって、hBN濃縮物を作った。その後、この分散に対して、実施例10で記述したポリアミド酸溶液51.3gを添加し、75%の速度で4分間、高せん断Silverson Homogenizerを用いて十分に混合した。このように作られたhBN濃縮物56.51gを、機械的撹拌器を用いて約20分間、29.84gのポリアミド酸溶液と混合して、硬化フィルム中に55重量%のhBNを含むポリアミド酸の分散/溶液を作った。25ミリグラムのアリコート中のODPAをこのように製造した分散/溶液に添加し、固形物が分散中に完全に溶解するまで、各アリコートについて約10分間混合した。合計2つのこのようなODPAアリコートを分散/溶液に添加して、分散/溶液の粘度を0.70s−1せん断速度で79200cpまで上昇させた。結果として得た分散/溶液を脱ガスし、フィルムへと流延し、実施例11の分散/溶液について記述した要領で後処理した。
実施例1で記述されている通りに、ただし表6に記されているような異なる相対的割合で、実施例1のSMhBNをポリアミド酸溶液と組合せ、ポリイミドフィルムに転換した。表6は、このように製造されたフィルムのCTEを示す。
実施例6〜8で製造したSMhBN試料を、一定範囲の割合全体にわたり、実施例11中の手順にしたがってポリアミド酸と組合わせ、表7中に列挙したSMhBN/ポリイミド複合フィルムを生成した。フィルムの平面に対して垂直な熱伝導率を決定し、その結果も表7に記した。
24.8gのODPAを4.25gのPMDAと組合わせて、混合物を形成した。このように形成した混合物を、2時間にわたり、350mlのDMAc中の29.2gの1,3−(4−アミノフェノキシ)ベンゼン(134APB)溶液にゆっくりと添加して、15%のポリアミド酸溶液を形成した。10000cpの粘度に達した後、実施例1のSMhBN11gを加え、充分撹拌して、細かい分散を得た。次に、連続撹拌しながら少量のPMDAをゆっくり添加することにより、ポリマーの粘度を75000センチポイズまで上昇させた。
25mlのメチルエチルケトン中に、9.0gのポリ(o−クレシルグリシジルエーテル)−コ−ホルムアルデヒド、(分子量1080、Aldrich、USA)、0.9gのPKHHフェノキシ樹脂(Phenoxy Specialties、Rock Hill、SC、USA)、0.9gのビスフェノールA、ジシクロペンタジエン−フェノール付加物である3.6gのDurite(登録商標)D_SD−1819(Borden Chemical Inc.、Louisville、KY)および0.86gの2−エチル−4−メチルイミダゾールを溶解させることにより、エポキシ樹脂組成物を製造した。このように形成したエポキシ溶液を、30分間室温で磁気撹拌器を用いて撹拌した。
受取ったままの状態でNX1hBNを使用したという点を除いて実施例24のフィルムと同一のフィルムを製造した。
そして同じ要領で、ただしhBNを一切使用しないで、追加のフィルムを製造した。
1.ポリマーと、その中に分散した複数の表面改質六方晶窒化ホウ素粒子とを含む、厚さ500μm未満のフィルムであって、前記表面改質窒化ホウ素粒子が、表面と該表面に結合した置換フェニルラジカルとを有する六方晶窒化ホウ素粒子を含み、置換フェニルラジカルが、構造:
は置換もしくは未置換アリールである]
により表わされる、上記フィルム。
2.R1が水素であり、XがNH2−である、上記1に記載のフィルム。
3.R1が水素であり、XがHO−である、上記1に記載のフィルム。
4.ポリマーがポリアミド酸である、上記1に記載のフィルム。
5.ポリマーがポリイミドである、上記1に記載のフィルム。
6.ポリマーが硬化したエポキシ樹脂組成物である、上記1に記載のフィルム。
7.ポリマーが未硬化エポキシ樹脂組成物である、上記1に記載のフィルム。
8.SMhBN粒子が、0.5〜50μmの範囲内の粒径を有する、上記1に記載のフィルム。
9.SMhBNの濃度が、30〜70質量%である、上記8に記載のフィルム。
10.溶媒中のポリマーの溶液中の複数の表面改質六方晶窒化ホウ素粒子の分散体を剥離表面上に流延するステップと、こうして流延した分散体を粘性液体フィルムに成形するステップと、溶媒を引き抜いて厚さ500μm未満のフィルムを成形するステップとを含む方法であって、表面改質六方晶窒化ホウ素粒子が、表面と該表面に結合した置換フェニルラジカルとを有する六方晶窒化ホウ素粒子を含み、置換フェニルラジカルは、構造:
で表わされる。上記方法。
11.R1が水素であり、XがNH2−である、上記10に記載の方法。
12.R1が水素であり、XがHO−である、上記10に記載の方法。
13.ポリマーがポリアミド酸である、上記1に記載の方法。
14.ポリマーが未硬化エポキシ樹脂組成物である、上記1に記載の方法。
15.SMhBN粒子が、0.5〜50μmの範囲内の粒径を有する、上記10に記載の方法。
Claims (2)
- ポリイミドまたは硬化エポキシ樹脂であるポリマーと、その中に分散した複数の表面改質六方晶窒化ホウ素粒子とを含む、厚さ500μm未満のフィルムであって、前記表面改質窒化ホウ素粒子が、表面と該表面に結合した置換フェニルラジカルとを有する六方晶窒化ホウ素粒子を含み、置換フェニルラジカルが、構造:
あり;ここで、R1がアルキルまたはアルコキシであり、R2が水素、アルキルまたは置換もしくは未置換アリールである]
により表わされる、上記フィルム。 - 溶媒中のポリマーの溶液中の複数の表面改質六方晶窒化ホウ素粒子の分散体を剥離表面上に流延するステップと、こうして流延した分散体を粘性液体フィルムに成形するステップと、溶媒を引き抜いて厚さ500μm未満のフィルムを成形するステップとを含む、ポリイミドまたは硬化エポキシ樹脂であるポリマーと、その中に分散した複数の表面改質六方晶窒化ホウ素粒子とを含む、厚さ500μm未満のフィルムを製造する方法であって、表面改質六方晶窒化ホウ素粒子が、表面と該表面に結合した置換フェニルラジカルとを有する六方晶窒化ホウ素粒子を含み、置換フェニルラジカルは、構造:
で表わされる、上記方法。
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US12/465,090 US8784980B2 (en) | 2009-05-13 | 2009-05-13 | Film prepared from a casting composition comprising a polymer and surface modified hexagonal boron nitride particles |
US12/465,090 | 2009-05-13 | ||
PCT/US2010/034471 WO2010132519A2 (en) | 2009-05-13 | 2010-05-12 | A film prepared from a casting composition comprising a polymer and surface modified hexagonal boron nitride particles |
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US8784980B2 (en) | 2009-05-13 | 2014-07-22 | E I Du Pont De Nemours And Company | Film prepared from a casting composition comprising a polymer and surface modified hexagonal boron nitride particles |
US8288466B2 (en) * | 2009-05-13 | 2012-10-16 | E I Du Pont De Nemours And Company | Composite of a polymer and surface modified hexagonal boron nitride particles |
US8440292B2 (en) * | 2009-05-13 | 2013-05-14 | E I Du Pont De Nemours And Company | Multi-layer article for flexible printed circuits |
CN102516766B (zh) * | 2011-11-29 | 2013-12-04 | 苏州大学 | 一种六方氮化硼/热固性树脂复合材料及其制备方法 |
KR102235501B1 (ko) * | 2014-09-12 | 2021-04-05 | 엘지이노텍 주식회사 | 무기충전재 및 이를 포함하는 에폭시 수지 조성물 |
KR102318231B1 (ko) | 2015-01-29 | 2021-10-27 | 엘지이노텍 주식회사 | 무기충전재, 이를 포함하는 수지 조성물, 그리고 이를 이용한 방열 기판 |
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-
2009
- 2009-05-13 US US12/465,090 patent/US8784980B2/en not_active Expired - Fee Related
-
2010
- 2010-05-12 EP EP10775448.3A patent/EP2430083A4/en not_active Withdrawn
- 2010-05-12 CN CN201080020671.4A patent/CN102421829B/zh not_active Expired - Fee Related
- 2010-05-12 JP JP2012510963A patent/JP5597700B2/ja not_active Expired - Fee Related
- 2010-05-12 KR KR1020117029682A patent/KR20120026539A/ko not_active Application Discontinuation
- 2010-05-12 WO PCT/US2010/034471 patent/WO2010132519A2/en active Application Filing
-
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WO2010132519A3 (en) | 2011-03-31 |
EP2430083A4 (en) | 2015-03-04 |
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JP2012526907A (ja) | 2012-11-01 |
US8784980B2 (en) | 2014-07-22 |
EP2430083A2 (en) | 2012-03-21 |
CN102421829B (zh) | 2014-05-07 |
HK1169429A1 (en) | 2013-01-25 |
WO2010132519A2 (en) | 2010-11-18 |
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