JP2017193655A - フッ素樹脂粒子分散体、樹脂組成物、金属張積層板、プリプレグ及び金属張積層板の製造方法 - Google Patents
フッ素樹脂粒子分散体、樹脂組成物、金属張積層板、プリプレグ及び金属張積層板の製造方法 Download PDFInfo
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- JP2017193655A JP2017193655A JP2016085286A JP2016085286A JP2017193655A JP 2017193655 A JP2017193655 A JP 2017193655A JP 2016085286 A JP2016085286 A JP 2016085286A JP 2016085286 A JP2016085286 A JP 2016085286A JP 2017193655 A JP2017193655 A JP 2017193655A
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Landscapes
- Reinforced Plastic Materials (AREA)
- Laminated Bodies (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
で表される熱分解性基を有する分散剤(A)と、フッ素樹脂粒子(B)と、水または有機溶剤(C)とを含有することを特徴とするフッ素樹脂粒子分散体を提供するものである。
で表される熱分解性基を有する分散剤(A)またはカルボキシル基を有する樹脂と、フッ素樹脂粒子(B)と、ポリイミド樹脂、シアネート樹脂、エポキシ樹脂、マレイミド樹脂、フェノール樹脂、トリアジン環を有する樹脂又はベンゾオキサジン環を有する樹脂あるいはそれらの半硬化物とを含有するプリプレグを提供するものである。
で表される熱分解性基を有する分散剤(A)またはカルボキシル基を有する樹脂と、フッ素樹脂粒子(B)と、ポリイミド樹脂、シアネート樹脂、エポキシ樹脂、マレイミド樹脂、フェノール樹脂、トリアジン環を有する樹脂又はベンゾオキサジン環を有する樹脂あるいはそれらの半硬化物が含浸してなるプリプレグを得たのち、金属箔を積層し、硬化させることを特徴とする金属張積層板の製造方法を提供するものである。
で表される熱分解性基を有することを特徴とする。
で表される構造単位を有する樹脂であることが好ましい。
測定装置:東ソー株式会社製「HLC−8220 GPC」、
カラム:東ソー株式会社製ガードカラム「HHR−H」(6.0mmI.D.×4cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
検出器:RI
データ処理:東ソー株式会社製「GPC−8020モデルIIデータ解析バージョン4.30」
測定条件:カラム温度 40℃
展開溶媒 テトラヒドロフラン(THF)
流速 1.0ml/分
試料:樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(5μl)。
標準試料:前記「GPC−8020モデルIIデータ解析バージョン4.30」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
東ソー株式会社製「F−288」
東ソー株式会社製「F−550」
で表される基であり、R62、R63はそれぞれ前記構造式(a1)で表される基又はカルボキシル基である。〕
で表される構造単位を有する、カルボキシル基を有する樹脂(但し、カルボキシル基を有する樹脂中のフッ素原子含有率は0.5質量%以下である。)となる。
製法1:カルボキシル基を有する重合性単量体(α)と、下記一般式(1)
で表されるビニルエーテル化合物と、を反応させてブロック化されたカルボキシル基を有する重合性単量体を得た後、該重合性単量体を重合させる方法。
で表されるもの等が挙げられる。
で表されるものが挙げられる。ポリアミック酸を加熱することで、構造中のアミド基とカルボキシル基との反応が進行してイミド基が形成され、これにより上述したようなポリイミド樹脂が得られる。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、アクリル酸26.8gと3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロ−1−ビニルオキシオクタン30.0gとを仕込み、乾燥空気気流下、室温(20〜28℃)にて21時間攪拌した。次いで、メトキノン0.003gとジイソプロピルエーテル107.6gを加え、飽和炭酸ナトリウム水溶液161.4g、イオン交換水161.4gを加えて分液した。次いで、上層を取り出した後、イオン交換水161.4gを加えて分液した。更に、上層を取り出した後、脱溶剤し、前記一般式(1)で表されるブロック化されたカルボキシル基を有する重合性単量体を得た。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、アクリル酸26.8gと3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロ−1−ビニルオキシオクタン30.0gとを仕込み、乾燥空気気流下、室温(20〜28℃)にて21時間攪拌した。次いで、メトキノン0.003gとジイソプロピルエーテル107.6gを加え、飽和炭酸ナトリウム水溶液161.4g、イオン交換水161.4gを加えて分液した。次いで、上層を取り出した後、イオン交換水161.4gを加えて分液した。更に、上層を取り出した後、脱溶剤し、前記一般式(1)で表されるブロック化されたカルボキシル基を有する重合性単量体を得た。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、アクリル酸26.8gと3,3,4,4,5,5,6,6,7,7,8,8,8−トリデカフルオロ−1−ビニルオキシオクタン30.0gとを仕込み、乾燥空気気流下、室温(20〜28℃)にて21時間攪拌した。次いで、メトキノン0.003gとジイソプロピルエーテル107.6gを加え、飽和炭酸ナトリウム水溶液161.4g、イオン交換水161.4gを加えて分液した。次いで、上層を取り出した後、イオン交換水161.4gを加えて分液した。更に、上層を取り出した後、脱溶剤し、前記一般式(1)で表されるブロック化されたカルボキシル基を有する重合性単量体を得た。
攪拌装置、温度計およびコンデンサーを付けたフラスコに、1,3−ジメチル−2−イミダゾリジノン(DMI)540.3gと、トリレンジイソシアネート15.7gと、4,4´−ジイソシアネート−3,3´−ジメチル−1,1´−ビフェニル95.0gと、無水トリメリット酸76.8gと、ベンゾフェノン−3,3′,4,4′−テトラカルボン酸二無水物32.2gとを仕込み、攪拌を行いながら発熱に注意して2時間かけて140℃まで昇温した後、この温度で22時間反応させた。反応は炭酸ガスの発泡とともに進行し、系内は黄色の透明液体となった。25℃での粘度が9Pa・sの樹脂固形分28%で溶液酸価が10(mgKOH/g)のポリアミドイミド樹脂(D1)のDMI溶液を得た。ゲルパーミエーションクロマトグラフィーの測定の結果、重量平均分子量は10,000であった。
ガラス製容器に、フッ素樹脂粒子〔ポリテトラフルオロエチレン(PTFE)の微粒子(平均一次粒子径0.3μm)、株式会社喜多村製「KTL−500F」)30部、分散剤(A1)を固形分換算で1.5部及びブチルセロソルブを加えて、100部とした。自転・公転真空ミキサー(株式会社シンキー製「ARE−250」)を用いて2000回転で2分間処理し、フッ素樹脂粒子分散体(1)を得た。
3:PTFEの微粒子のわずかな沈殿が確認されるが、振とうすると再分散可能。
2:PTFEの微粒子の沈降が確認されるが、振とうすると再分散可能。
1:PTFEの微粒子が沈降し、振とうしても再分散できない(ハードケーキ化)。
分散剤(A1)を用いるかわりに分散剤(A2)を用いた以外は実施例1と同様にしてフッ素樹脂粒子分散体(2)を得た。実施例1と同様の評価を行い、その結果を第1表に示す。
分散剤(A1)を用いるかわりに分散剤(A3)を用いた以外は実施例1と同様にしてフッ素樹脂粒子分散体(3)を得た。実施例1と同様の評価を行い、その結果を第1表に示す。
分散剤(A1)を用いるかわりに非熱分解性のフッ素系化合物(DIC株式会社製のフッ素系界面活性剤 メガファックF−555)を用いた以外は実施例1と同様にして比較対照用フッ素樹脂粒子分散体(1’)を得た。実施例1と同様の評価を行い、その結果を第1表に示す。
分散剤(A1)を用いるかわりに非熱分解性のフッ素系化合物(DIC株式会社製のフッ素系界面活性剤 メガファックF−558)を用いた以外は実施例1と同様にして比較対照用フッ素樹脂粒子分散体(2’)を得た。実施例1と同様の評価を行い、その結果を第1表に示す。
分散剤(A1)を用いなかった以外は実施例1と同様にして比較対照用フッ素樹脂粒子分散体(3’)を得た。実施例1と同様の評価を行い、その結果を第1表に示す。
ポリアミドイミド樹脂(D1)のDMI溶液100部、硬化剤としてビスフェノール型エポキシ樹脂〔DIC株式会社製EPICLON850−S、エポキシ当量184〕7.25部、触媒として1,2−ジメチルイミダゾールを固形分に対し0.1質量%を混合し、DMIを用いて35質量%に希釈した樹脂溶液を作成した。この溶液5.0部に対し、分散剤(A1)を1.2質量部、DMI4.3部を配合して、樹脂組成物(1)を調製した。得られた樹脂組成物(1)を用いて硬化膜を得て、その硬化膜の水、プロピレングリコールモノメチルエーテルアセテート(PGMEA)及びn−メチルピロリドン(NMP)の接触角(°)を測定した。評価結果を第2表に示す。
樹脂組成物(1)を7cm×7cmのガラス板上に回転数1000rpmで10秒間スピンコーティングした後、100℃で30分乾燥した後、200℃で1時間の条件で加熱して硬化膜を形成した。
分散剤(A1)を用いるかわりに分散剤(A2)を用いた以外は実施例4と同様にして樹脂組成物(2)を得た。実施例4と同様の評価を行い、その結果を第2表に示す。
分散剤(A1)を用いるかわりに分散剤(A3)を用いた以外は実施例4と同様にして樹脂組成物(3)を得た。実施例4と同様の評価を行い、その結果を第2表に示す。
分散剤(A1)を用いるかわりにDIC株式会社製のフッ素系界面活性剤 メガファックF−555を用いた以外は実施例4と同様にして比較対照樹脂組成物(1’)を得た。実施例4と同様の評価を行い、その結果を第2表に示す。
分散剤(A1)を用いるかわりにDIC株式会社製のフッ素系界面活性剤 メガファックF−558を用いた以外は実施例4と同様にして比較対照用樹脂組成物(2’)を得た。実施例4と同様の評価を行い、その結果を第2表に示す。
分散剤(A1)を用いなかった以外は実施例4と同様にして比較対照用樹脂組成物(3’)を得た。実施例4と同様の評価を行い、その結果を第2表に示す。
実施例1で得られたフッ素樹脂粒子分散体(1)をフッ素樹脂粒子として20質量%、シリカ粒子(アドマテックス社製、SO25R、平均粒子径0.5μm)39.7質量%、エポキシ樹脂(日本化薬株式会社製、NC3000、ビフェニルアラルキル型エポキシ樹脂、エポキシ当量:276g/eq)11.2質量%、シアネート樹脂(LONZA社製、Primaset PT−30、フェノールノボラック型シアネート樹脂)20.0質量%、フェノール樹脂(明和化成株式会社製、MEH7851)8.8質量%、エポキシシランカップリング剤(日本ユニカー社製、A187)0.3質量%を、メチルエチルケトンに溶解・混合させ、高速撹拌装置を用い撹拌して、固形分基準で70質量%の樹脂組成物を得た。この樹脂組成物に嵩比重45g/cm2のガラス繊維を含浸して引き上げたのち、室温にて乾燥させたのち、180℃で10分間加熱することに依りプリプレグを得た。このプリプレグ4枚を更に積層し、その外側両面に厚さ3μmの銅箔を積層し、金型に挟持して圧力1MPa、温度220℃で2時間加熱加圧成形して銅張積層板を得た。この銅張積層板の引きはがし強さをJIS C6481に準拠して測定したところ、1.0kN/m以上となり、良好であることを確認した。
実施例7において、分散体(1)の代わりに分散体(2)、分散体(3)を用いる以外は実施例7と同様にして銅張積層板を得た。これらの積層板における引きはがし強さを同様にして測定したところ、いずれも1.0kN/m以上であった。
実施例7において、分散体(1)の代わりに分散体(1’)を用いる以外は実施例7と同様にして銅張積層板を得た。これを用いて引きはがし強さを測定したところ、0.7kN/mであり、実施例よりも密着性に劣ることが確認できた。
Claims (14)
- 前記構造式(1)中のR4が、フッ素原子が直接結合した炭素原子の数が1〜6のフッ素化アルキル基である請求項1記載のフッ素樹脂粒子分散体。
- 前記構造式(1)中のR1、R2およびR3がそれぞれ水素原子である請求項1又は2記載のフッ素樹脂粒子分散体。
- 前記分散剤(A)が、さらに分子量200〜2,500のオキシアルキレン鎖を有するものである請求項1〜3の何れか1項記載のフッ素樹脂粒子分散体。
- 前記オキシアルキレン鎖が、ポリエチレングリコール鎖、ポリプロピレングリコール鎖又はポリブチレングルコール鎖である請求項4記載のフッ素樹脂粒子分散体。
- 前記フッ素樹脂粒子(B)がポリテトラフルオロエチレンの粒子である請求項1〜6の何れか1項記載のフッ素樹脂粒子分散体。
- 前記樹脂(D)が、ポリイミド樹脂、シアネート樹脂、エポキシ樹脂、マレイミド樹脂、トリアジン環を有する樹脂又はベンゾオキサジン環を有する樹脂である請求項8記載の樹脂組成物。
- 請求項8又は9記載の樹脂組成物の硬化物。
- 請求項8又は9記載の樹脂組成物の硬化物と金属箔とを含む金属張積層板。
- 前記金属箔が銅箔である請求項11記載の金属張積層板。
- 繊維基材と、下記構造式(a1)
で表される熱分解性基を有する分散剤(A)またはカルボキシル基を有する樹脂と、フッ素樹脂粒子(B)と、ポリイミド樹脂、シアネート樹脂、エポキシ樹脂、マレイミド樹脂、フェノール樹脂、トリアジン環を有する樹脂又はベンゾオキサジン環を有する樹脂あるいはそれらの半硬化物とを含有するプリプレグ。 - 繊維基材に、下記構造式(a1)
で表される熱分解性基を有する分散剤(A)またはカルボキシル基を有する樹脂と、フッ素樹脂粒子(B)と、ポリイミド樹脂、シアネート樹脂、エポキシ樹脂、マレイミド樹脂、フェノール樹脂、トリアジン環を有する樹脂又はベンゾオキサジン環を有する樹脂あるいはそれらの半硬化物が含浸してなるプリプレグを得たのち、金属箔を積層し、硬化させることを特徴とする金属張積層板の製造方法。
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