JP6268564B2 - オキサジン化合物、組成物及び硬化物 - Google Patents
オキサジン化合物、組成物及び硬化物 Download PDFInfo
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- JP6268564B2 JP6268564B2 JP2017539686A JP2017539686A JP6268564B2 JP 6268564 B2 JP6268564 B2 JP 6268564B2 JP 2017539686 A JP2017539686 A JP 2017539686A JP 2017539686 A JP2017539686 A JP 2017539686A JP 6268564 B2 JP6268564 B2 JP 6268564B2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/16—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with only hydrogen or carbon atoms directly attached in positions 2 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
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Description
従来のベンゾオキサジンとしては、ビスフェノールFやビスフェノールAなどの二官能フェノール類とアニリンとからなるベンゾオキサジンが、特許文献1、特許文献2にて開示されている。しかし、これらの使用に際してはオキサジンの開環時にアニリン由来の成分が分解ガスとして発生するために、長期熱耐久性の指標となる耐熱分解性において、近年要求されているレベルには達していないことから、更なる改良、性能の向上が強く望まれている。
更に式(1)の化合物は炭素数1〜3のアルキル基、置換または無置換の芳香族基を有していてもよい。)
(式(2)中、X1、X2、Y1はそれぞれ独立して単結合または2価の連結基を表し、R2は、水素原子、炭化水素基、又は、炭化水素基に含まれる1以上の水素原子が水酸基、アルコキシ基、ハロゲン原子のいずれかで置換された炭化水素基を表し、a1は、前記オキサジン化合物(1)との結合点であることを表す。)
本発明のオキサジン化合物は、一般式(1)の構造を有し、さらに一般式(2)で表される官能基R1をそれぞれ独立して少なくとも2個以上有することを特徴とする。
更に式(1)の化合物は炭素数1〜3のアルキル基、置換または無置換の芳香族基を有していてもよい。)
本発明において、官能基R1は炭素−炭素間三重結合構造を有する基であり、具体的には前記式(2)で表される基である。本発明のオキサジン化合物は、オキサジン環の開環重合に由来する硬化反応と、炭素−炭素間三重結合の重合反応に由来する硬化反応の2つの硬化が進行するため、硬化した際に密な架橋構造を形成することから、耐熱性、特に耐熱分解温度が向上する。特に、本発明のオキサジン化合物は、官能基R1を2つ以上有することを特徴としており、これは多官能化することで硬化物がより密な三次元架橋を形成し、より一層耐熱性が向上するためである。
アルケニレン基としては、ビニレン基、1−メチルビニレン基、プロペニレン基、ブテニレン基、ペンテニレン基等が挙げられる。
アルキニレン基としては、エチニレン基、プロピニレン基、ブチニレン基、ペンチニレン基、へキシニレン基等が挙げられる。
シクロアルキレン基としては、シクロプロピレン基、シクロブチレン基、シクロペンチレン基、シクロへキシレン基等が挙げられる。
アリーレン基としては、フェニレン基、トリレン基、キシリレン基、ナフチレン基等が挙げられる。
アラルキレン基としては、アルキレン基とアリーレン基を有する炭素数7〜20のアラルキレン基等が挙げられる。
前記式(1)の化合物においてAr1は、置換または無置換の芳香族基を表し、具体的にはフェニレン基、ナフチレン基、アントラセン骨格やフェナントレン骨格を含むアリーレン基等が挙げられる。
本発明のオキサジン化合物は、分子骨格に反応性官能基を導入したフェノール化合物、同じく反応性官能基を導入した芳香族アミノ化合物をホルムアルデヒドとを反応させることで得ることができる。反応性官能基としては、エチニル基、プロパルギルオキシ基などが挙げられる。反応性官能基を導入したフェノール化合物としては、2-プロパルギルオキシフェノール、3-プロパルギルオキシフェノール、4-プロパルギルオキシフェノール、4’−プロパルギルオキシ−4−ビフェノール、4’−プロパルギルオキシ−3−ビフェノール、4’−プロパルギルオキシ−2−ビフェノール、2-プロパルギルオキシ−1−ナフトール、3-プロパルギルオキシ−1−ナフトール、4-プロパルギルオキシ−1−ナフトール、5-プロパルギルオキシ−1−ナフトール、6-プロパルギルオキシ−1−ナフトール、7-プロパルギルオキシ−1−ナフトール、8-プロパルギルオキシ−1−ナフトール、1-プロパルギルオキシ−2−ナフトール、3-プロパルギルオキシ−2−ナフトール、6-プロパルギルオキシ−2−ナフトール、7-プロパルギルオキシ−2−ナフトールなどが挙げられる。反応性官能基を導入した芳香族アミノ化合物としては、2-プロパルギルオキシアニリン、3-プロパルギルオキシアニリン、4-プロパルギルオキシアニリン、4’−プロパルギルオキシビフェニル−4−アミン、4’−プロパルギルオキシビフェニル−3−アミン、4’−プロパルギルオキシビフェニル−2−アミン、2-プロパルギルオキシ−1−アミノナフタレン、3-プロパルギルオキシ−1−アミノナフタレン、4-プロパルギルオキシ−1−アミノナフタレン、5-プロパルギルオキシ−1−アミノナフタレン、6-プロパルギルオキシ−1−アミノナフタレン、7-プロパルギルオキシ−1−アミノナフタレン、8-プロパルギルオキシ−1−アミノナフタレン、1-プロパルギルオキシ−2−アミノナフタレン、3-プロパルギルオキシ−2−アミノナフタレン、6-プロパルギルオキシ−2−アミノナフタレン、7-プロパルギルオキシ−2−アミノナフタレンなどが挙げられる。反応は、例えば反応性官能基を導入したフェノール化合物、反応性官能基を導入した芳香族アミノ化合物を、ホルムアルデヒドと50〜100℃の温度条件下で反応を行い、反応終了後に水層と有機層とを分離した後、有機層から有機溶媒を減圧乾燥させるなどしてオキサジン化合物を得ることが出来る。
また、ホルムアルデヒドは、溶液の状態であるホルマリン、或いは固形の状態であるパラホルムアルデヒドのどちらの形態で用いても良い。
本発明の樹脂組成物は、本発明のオキサジン化合物を含有する。
本発明の樹脂組成物を硬化して得られる硬化物は、耐熱分解性に優れ、なおかつ誘電特性及び低吸湿性に優れることから、耐熱部材や電子部材に好適に使用可能である。
本発明の樹脂組成物は、本発明のオキサジン化合物以外の配合物を有していてもよい。
例えば、本発明のオキサジン化合物以外の反応性化合物を有していてもよい。ここで言う反応性化合物とは、反応性基を有する化合物であり、モノマーであってもオリゴマーであってもポリマーであってもかまわない。
本発明のオキサジン化合物と反応する官能基としては、例えばエポキシ基、シアナト基、マレイミド基、フェノール性水酸基が挙げられる。
シアナト基を有する化合物としては、シアネートエステル樹脂が挙げられる。
マレイミド基を有する化合物としては、マレイミド樹脂、ビスマレイミド化合物が挙げられる。フェノール性水酸基を有する化合物としては、フェノール樹脂、フェノール化合物が挙げられる。
本発明の組成物は、オキサジン化合物の他に、更にフィラーを含有してもよい。フィラーとしては、無機フィラーと有機フィラーが挙げられる。無機フィラーとしては、例えば無機微粒子が挙げられる。
これらの無機微粒子は、用途によって適時選択すればよく、単独で使用しても、複数種組み合わせて使用してもかまわない。また、上記無機微粒子は、例に挙げた特性以外にも様々な特性を有することから、適時用途に合わせて選択すればよい。
また、市販のコロイダルシリカとしては、例えば、日産化学工業(株)製メタノ−ルシリカゾル、IPA−ST、MEK−ST、NBA−ST、XBA−ST、DMAC−ST、ST−UP、ST−OUP、ST−20、ST−40、ST−C、ST−N、ST−O、ST−50、ST−OL等を挙げることができる。
本発明の組成物は、オキサジン化合物の他に、更に繊維質基質を含有してもよい。本発明の繊維質基質は、特に限定はないが、繊維強化樹脂に用いられるものが好ましく、無機繊維や有機繊維が挙げられる。
本発明の組成物は、組成物の固形分量や粘度を調整する目的として、分散媒を使用してもよい。分散媒としては、本発明の効果を損ねることのない液状媒体であればよく、各種有機溶剤、液状有機ポリマー等が挙げられる。
また、本発明の組成物は、オキサジン化合物以外の樹脂を有していてもよい。樹脂としては、本発明の効果を損なわない範囲であれば公知慣用の樹脂を配合すればよく、例えば
熱硬化性樹脂や熱可塑性樹脂を用いることができる。
本発明の組成物は、配合物に応じて硬化剤を用いてもよい、例えば、エポキシ基を有する化合物を配合している場合には、アミン系硬化剤、アミド系硬化剤、酸無水物系硬化剤、フェノール系硬化剤、アミノトリアジンノボラック樹脂、活性エステル樹脂、カルボキシル基やチオールなどのエポキシ基と反応する官能基を有する樹脂などの各種の硬化剤を併用してもかまわない。
これらの硬化剤は、単独でも2種類以上の併用でも構わない。
本発明の組成物は、その他の配合物を有していてもかまわない。例えば、触媒、重合開始剤、無機顔料、有機顔料、体質顔料、粘土鉱物、ワックス、界面活性剤、安定剤、流動調整剤、カップリング剤、染料、レベリング剤、レオロジーコントロール剤、紫外線吸収剤、酸化防止剤、難燃剤、可塑剤等が挙げられる。
本発明の組成物を硬化して得られる硬化物は、耐熱分解性、誘電特性及び低吸湿性に優れることから、耐熱部材や電子部材に好適に使用可能である。硬化物の成形方法は特に限定は無く、組成物単独で成形してもよいし、基材と積層することで積層体としてもかまわない。
回路基板や半導体パッケージ基板といった用途の場合、金属箔を積層することが好ましく、金属箔としては銅箔、アルミ箔、金箔、銀箔などが挙げられ、加工性が良好なことから銅箔を用いることが好ましい。
成形された組成物を積層する場合、未硬化または半硬化された組成物層を積層してから硬化させてもよいし、組成物を完全硬化した硬化物層を基材に対し積層してもよい。
また、本発明の硬化物に対して、基材となりうる前駆体を塗工して硬化させることで積層させてもよく、基材となりうる前駆体または本発明の組成物が未硬化あるいは半硬化の状態で接着させた後に硬化させてもよい。基材となりうる前駆体としては特に限定はなく、各種硬化性樹脂組成物等が挙げられる。
本発明の組成物が繊維質基質を有し、該繊維質基質が強化繊維の場合、繊維質基質を含有する組成物は繊維強化樹脂として用いることができる。
組成物に対し繊維質基質を含有させる方法は、本発明の効果を損なわない範囲であればとくに限定はなく、繊維質基質と組成物とを、混練、塗布、含浸、注入、圧着、等の方法で複合化する方法が挙げられ、繊維の形態及び繊維強化樹脂の用途によって適時選択することができる。
本発明の繊維強化樹脂は、未硬化あるいは半硬化のプリプレグと呼ばれる状態を形成することができる。プリプレグの状態で製品を流通させた後、最終硬化をおこなって硬化物を形成してもよい。積層体を形成する場合は、プリプレグを形成した後、その他の層を積層してから最終硬化を行うことで、各層が密着した積層体を形成できるため、好ましい。
この時用いる組成物と繊維質基質の質量割合としては、特に限定されないが、通常、プリプレグ中の樹脂分が20〜60質量%となるように調製することが好ましい。
本発明のオキサジン化合物は、その硬化物が耐熱分解性、誘電特性及び低吸湿性に優れることから、耐熱部材や電子部材に好適に使用可能である。特に、半導体封止材、回路基板、ビルドアップフィルム、ビルドアップ基板等に好適に使用可能である。また、繊維強化樹脂のマトリクス樹脂にも好適に使用可能であり、高耐熱性のプリプレグとして特に適している。こうして得られる耐熱部材や電子部材は、各種用途に好適に使用可能であり、例えば、産業用機械部品、一般機械部品、自動車・鉄道・車両等部品、宇宙・航空関連部品、電子・電気部品、建築材料、容器・包装部材、生活用品、スポーツ・レジャー用品、風力発電用筐体部材等が挙げられるが、これらに限定される物ではない。
本発明の組成物から半導体封止材料を得る方法としては、前記組成物、及び硬化促進剤、及び無機充填剤等の配合剤とを必要に応じて押出機、ニ−ダ、ロ−ル等を用いて均一になるまで充分に溶融混合する方法が挙げられる。その際、無機充填剤としては、通常、溶融シリカが用いられるが、パワートランジスタ、パワーIC用高熱伝導半導体封止材として用いる場合は、溶融シリカよりも熱伝導率の高い結晶シリカ,アルミナ,窒化ケイ素などの高充填化、または溶融シリカ、結晶性シリカ、アルミナ、窒化ケイ素などを用いるとよい。その充填率は硬化性樹脂組成物100質量部当たり、無機充填剤を30〜95質量%の範囲で用いることが好ましく、中でも、難燃性や耐湿性や耐ハンダクラック性の向上、線膨張係数の低下を図るためには、70質量部以上がより好ましく、80質量部以上であることがさらに好ましい。
本発明の硬化性樹脂組成物から半導体装置を得る半導体パッケージ成形としては、上記半導体封止材料を注型、或いはトランスファー成形機、射出成形機などを用いて成形し、さらに50〜250℃で2〜10時間の間、加熱する方法が挙げられる。
本発明の組成物からプリント回路基板を得る方法としては、上記プリプレグを、常法により積層し、適宜銅箔を重ねて、1〜10MPaの加圧下に170〜300℃で10分〜3時間、加熱圧着させる方法が挙げられる。
本発明の組成物からビルドアップ基板を得る方法は、例えば以下の工程が挙げられる。まず、ゴム、フィラーなどを適宜配合した上記組成物を、回路を形成した回路基板にスプレーコーティング法、カーテンコーティング法等を用いて塗布した後、硬化させる工程(工程1)。その後、必要に応じて所定のスルーホール部等の穴あけを行った後、粗化剤により処理し、その表面を湯洗することによって凹凸を形成させ、銅などの金属をめっき処理する工程(工程2)。このような操作を所望に応じて順次繰り返し、樹脂絶縁層及び所定の回路パターンの導体層を交互にビルドアップして形成する工程(工程3)。なお、スルーホール部の穴あけは、最外層の樹脂絶縁層の形成後に行う。また、本発明のビルドアップ基板は、銅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、170〜300℃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。
本発明の組成物からビルドアップフィルムを得る方法としては、基材である支持フィルム(Y)の表面に、上記組成物を塗布し、更に加熱、あるいは熱風吹きつけ等により有機溶剤を乾燥させて組成物の層(X)を形成させることにより製造することができる。
本発明の組成物から導電ペーストを得る方法としては、例えば、導電性粒子を該組成物中に分散させる方法が挙げられる。上記導電ペーストは、用いる導電性粒子の種類によって、回路接続用ペースト樹脂組成物や異方性導電接着剤とすることができる。
尚、1Hおよび13C−NMR、MSスペクトル、IRは以下の条件にて測定した。
磁場強度:600MHz
積算回数:16回
溶媒:DMSO−d6
試料濃度:30質量%
磁場強度:150MHz
積算回数:4000回
溶媒:DMSO−d6
試料濃度:30質量%
測定範囲:m/z=50.00〜2000.00
変化率:25.6mA/min
最終電流値:40mA
カソード電圧:−10kV
滴下ロート、温度計、攪拌装置、加熱装置、冷却還流管を取り付けた4つ口フラスコに窒素ガスを流しながら、4-プロパルギルオキシアニリン147.2g(1.0モル)、4-プロパルギルオキシフェノール148.2g(1.0モル)を仕込み、トルエン 750gに溶解させた後、94%パラホルムアルデヒド63.9g(2.0モル)を加えて、攪拌しながら80℃まで昇温し、80℃で7時間反応させた。反応後、分液ロートに移し、水層を除去した。その後有機層から溶媒を加熱減圧下に除去し、オキサジン化合物(A−1)239gを得た。
1H−NMRは7.04ppm(2H)、6.87ppm(2H)、6.75ppm(2H)、6.62ppm(1H)、5.22ppm(2H)、4.59ppm(4H)、4.51ppm(2H)、2.49ppm(2H)のピークを示し、13C−NMRは152.8ppm、151.5ppm、149.0ppm、143.1ppm、121.3ppm、120.5ppm、117.5ppm、115.7ppm、115.0ppm、112.9ppm、80.4ppm、78.8ppm、78.8ppm、75.4ppm、75.4ppm、56.5ppm、56.2ppm、51.1ppmのピークを示し、マススペクトルはM+=319のピークを示したことから、下記式で表されるオキサジン化合物(A−1)が得られていることを確認した。
滴下ロート、温度計、攪拌装置、加熱装置、冷却還流管を取り付けた4つ口フラスコに窒素ガスを流しながら、4,4´−ビフェノール 400.0g(2.1モル)と脱水THF 5000mLを仕込み攪拌溶解した。反応溶液を10℃以下に保ちながら水素化ナトリウム(60%, 流動パラフィンに分散) 85.9g(2.1モル)を1時間かけて分割添加した。1時間かけて室温に戻した後、昇温し還流状態にした。還流下でプロパルギルブロミド(80%トルエン溶液) 319.4g(2.1モル)を1時間かけて滴下した。滴下終了後、還流下で24時間反応させた。
室温まで放冷後、臭化ナトリウムを濾別し、THF及びトルエンを減圧除去した。残渣に酢酸エチル 3600gを加え溶解させた後、10%水酸化ナトリウム水溶液1200gを用い3回アルカリ洗浄した。続いてイオン交換水 1800g用い2回水洗した。硫酸ナトリウムを加え乾燥後、濾別し酢酸エチルを減圧除去した。60℃で12時間真空乾燥し乳白色固体(C−1)を76.0g得た。1H−NMRは9.44ppm(1H)、7.51ppm−7.40ppm(4H)、7.01ppm(2H)、6.81ppm(2H)、4.80ppm(2H)、3.55ppm(1H)のピークを示し、13C−NMRは156.6ppm、156.0ppm、133.5ppm、130.6ppm、127.3ppm、126.9ppm、115.6ppm、115.5ppm、115.2ppm、79.3ppm、78.1ppm、55.4ppmのピークを示し、目的物であるモノプロパルギルエーテルを含有する混合物(C−1)であることを確認した。
<混合物(C−1)の組成>
モノプロパルギルエーテル 52.1%
ジプロパルギルエーテル 44.9%
HPLC面積% 検出波長254nm
滴下ロート、温度計、攪拌装置、加熱装置、冷却還流管を取り付けた4つ口フラスコに窒素ガスを流しながら、4,4´−ビフェノール 400.0g(2.1モル)と脱水THF 3000mLを仕込み攪拌溶解した。反応溶液を10℃以下に保ちながら水素化ナトリウム(60%, 流動パラフィンに分散) 43.0g(1.1モル)を1時間かけて分割添加した。1時間かけて室温に戻した後、昇温し還流状態にした。還流下でプロパルギルブロミド(80%トルエン溶液) 159.7g(1.1モル)を1時間かけて滴下した。滴下終了後、還流下で24時間反応させた。
室温まで放冷後、臭化ナトリウムを濾別し、THF及びトルエンを減圧除去した。残渣に酢酸エチル 2000gを加え溶解させた後、10%水酸化ナトリウム水溶液1200gを用い3回アルカリ洗浄した。続いてイオン交換水 1800g用い2回水洗した。硫酸ナトリウムを加え乾燥後、濾別し酢酸エチルを減圧除去した。60℃で12時間真空乾燥し乳白色固体(C−2)を98.7g得た。1H−NMRは9.44ppm(1H)、7.51ppm−7.40ppm(4H)、7.01ppm(2H)、6.81ppm(2H)、4.80ppm(2H)、3.55ppm(1H)のピークを示し、13C−NMRは156.6ppm、156.0ppm、133.5ppm、130.6ppm、127.3ppm、126.9ppm、115.6ppm、115.5ppm、115.2ppm、79.3ppm、78.1ppm、55.4ppmのピークを示し、目的物であるモノプロパルギルエーテルを含有する混合物(C−2)であることを確認した。
<混合物(C−2)の組成>
モノプロパルギルエーテル 81.7%
ジプロパルギルエーテル 18.3%
HPLC面積% 検出波長254nm
滴下ロート、温度計、攪拌装置、加熱装置、冷却還流管を取り付けた4つ口フラスコに窒素ガスを流しながら、4-プロパルギルオキシアニリン29.4g(0.2モル)、モノプロパルギルエーテル含有混合物(C−1)76.0gを仕込み、トルエン150gに溶解させた後、94%パラホルムアルデヒド12.8g(0.4モル)を加えて、攪拌しながら80℃まで昇温し、80℃で7時間反応させた。反応後、分液ロートに移し、水層を除去した。その後有機層から溶媒を加熱減圧下に除去し、オキサジン化合物(A−2)を含有する反応物84.9gを得た。
実施例2において、混合物(C−1)を(C−2)に代える以外は、同様の操作を行い、オキサジン化合物A−2の純度が91%である反応物(A−2−2)108.3gを得た。
滴下ロート、温度計、攪拌装置、加熱装置、冷却還流管を取り付けた4つ口フラスコに窒素ガスを流しながら、アニリン93.1g(1.0モル)、フェノール94.1g(1.0モル)を仕込み、トルエン 750gに溶解させた後、94%パラホルムアルデヒド63.9g(2.0モル)を加えて、攪拌しながら80℃まで昇温し、80℃で7時間反応させた。反応後、分液ロートに移し、水層を除去した。その後有機層から溶媒を加熱減圧下に除去し、オキサジン化合物(B−1)189gを得た。
1H−NMRは7.24ppm−7.05ppm(7H)、6.87ppm−6.70ppm(2H)、5.43ppm(2H)、4.64ppm(2H)のピークを示し、13C−NMRは154.0ppm、147.8ppm、129.1ppm、127.7ppm、127.2ppm、121.3ppm、120.5ppm、120.5ppm、117.4ppm、116.2ppm、78.4ppm、48.9ppmのピークを示し、マススペクトルはM+=211のピークを示したことから、下記式で表されるオキサジン化合物(B−1)が得られていることを確認した。
滴下ロート、温度計、攪拌装置、加熱装置、冷却還流管を取り付けた4つ口フラスコに窒素ガスを流しながら、1,4−ハイドロキノン 40.0g(0.4モル)とアセトン 1Lを仕込み攪拌溶解した。炭酸カリウム 110.5g(0.8モル)を添加後、昇温し還流状態にした。還流下で30分経過後、プロパルギルブロミド(80%トルエン溶液) 118.8g(0.8モル)を1時間かけて滴下した。滴下終了後、還流下で24時間反応させた。
室温まで放冷後、炭酸カリウムを濾別し、アセトンを減圧除去した。残渣にクロロホルム 200mLを加え溶解させた後、イオン交換水 200mLを用い2回水洗した。硫酸マグネシウムを加え乾燥後、濾別しクロロホルムを減圧除去した。さらに80℃で12時間真空乾燥し薄茶色結晶を64g得た。1H−NMRは6.93ppm−6.86ppm(4H)、4.70ppm(4H)、3.51ppm(2H)のピークを示し、13C−NMRは151.7ppm、115.8ppm、79.4ppm、78.0ppm、55.8ppmのピークを示し、下記式で表される目的物である1,4−ハイドロキノンジプロパルギルエーテルであることを確認した。
実施例1〜3及び比較合成例1で得られたオキサジン化合物(A−1、A−2−1、A−2−2、B−1)、比較合成例2で得られた1,4−ハイドロキノンジプロパルギルエーテル(B−2)、比較用ジヒドロオキサジン化合物(四国化成製「P−d型ベンゾオキサジン」(4,4’−ジアミノジフェニルメタンとホルマリンとフェノールの反応生成物))、フェノール樹脂(DIC株式会社製「TD−2131」フェノールノボラック樹脂)を、表1に示す割合で配合し、組成物を調製した。
この組成物を以下の条件に付すことで硬化物を作製した。
硬化条件:170℃で2時間の後、200℃で2時間、更に250℃で2時間加熱硬化
成型後板厚:2.4mm
<ガラス転移温度>
厚さ2.4mmの硬化物を幅5mm、長さ54mmのサイズに切り出し、これを試験片1とした。この試験片1を粘弾性測定装置(DMA:日立ハイテクサイエンス社製固体粘弾性測定装置「DMS7100」、変形モード:両持ち曲げ、測定モード:正弦波振動、周波数1Hz、昇温速度3℃/分)を用いて、弾性率変化が最大となる(tanδ変化率が最も大きい)温度をガラス転移温度として評価した。
厚さ2.4mmの硬化物を細かく裁断し、熱重量分析装置(SIIナノテクノロジー社製「TG/DTA6200」)を用いて、昇温速度を5℃/分として窒素雰囲気下で測定を行い、5%重量減少する温度(Td5)を求めた。
Claims (17)
- 一般式(1−1)で表されることを特徴とするオキサジン化合物。
・・・(1−1)
(式(1−1)中、Ar1は置換または無置換の芳香族基を表し、環Aは置換または無置換の芳香環を表し、R1はそれぞれ独立して下記一般式(2)で示される官能基であって、R3およびR4はそれぞれ独立して水素原子、炭素数1〜3のアルキル基、置換または無置換の芳香族基を表す。)
・・・(2)
(式(2)中、X1、X2、Y1はそれぞれ独立して単結合または2価の連結基を表し、当該2価の連結基としては酸素原子、2価の炭化水素基、又は2価の炭化水素基に含まれる1以上の水素原子が、水酸基、アルコキシ基、又はハロゲン原子で置換された2価の基、カルボニル基(−CO−基)、エステル基(−COO−基)、アミド基(−CONH−基)、イミノ基(−C=N−基)、アゾ基(−N=N−基)、スルフィド基(−S−基)、スルホン基(−SO 3 −基)、及びこれらを組み合わせてなる2価の連結基であって、
R2は、水素原子、炭化水素基、又は、炭化水素基に含まれる1以上の水素原子が水酸基、アルコキシ基、ハロゲン原子のいずれかで置換された炭化水素基を表し、a1は、前記オキサジン化合物(1−1)との結合点であることを表す。) - 環Aが置換または無置換のベンゼン環、置換または無置換のナフタレン環である、請求項1に記載のオキサジン化合物。
- 請求項1または2に記載のオキサジン化合物を含有することを特徴とする、組成物。
- 更に、反応性化合物を含有する、請求項3に記載の組成物。
- 更に、フィラーを含有する、請求項3または4に記載の組成物。
- 更に、繊維質基質を含有する、請求項3〜5のいずれかに記載の組成物。
- 請求項3〜6のいずれかに記載の組成物を硬化してなる硬化物。
- 基材と請求項7に記載の硬化物層とを有することを特徴とする積層体。
- 請求項3〜6のいずれかに記載の組成物を含有することを特徴とする、耐熱材料用組成物。
- 請求項7に記載の硬化物を含有することを特徴とする耐熱部材。
- 請求項3〜6のいずれかに記載の組成物を含有することを特徴とする、電子材料用組成物。
- 請求項7に記載の硬化物を含有することを特徴とする電子部材。
- 請求項3〜6のいずれかに記載の組成物を含有することを特徴とする、半導体封止材。
- 請求項6に記載の、繊維質基質を含有する組成物を含有することを特徴とするプリプレグ。
- 請求項14に記載のプリプレグに更に銅箔層を有することを特徴とする回路基板。
- ビルドアップフィルムである、請求項8に記載の積層体。
- 請求項16に記載のビルドアップフィルムを有することを特徴とするビルドアップ基板。
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US5543516A (en) * | 1994-05-18 | 1996-08-06 | Edison Polymer Innovation Corporation | Process for preparation of benzoxazine compounds in solventless systems |
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