JP6861843B2 - 熱硬化性樹脂組成物、それを用いて製造されたプリプレグおよび金属箔張積層板 - Google Patents
熱硬化性樹脂組成物、それを用いて製造されたプリプレグおよび金属箔張積層板 Download PDFInfo
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- JP6861843B2 JP6861843B2 JP2019554844A JP2019554844A JP6861843B2 JP 6861843 B2 JP6861843 B2 JP 6861843B2 JP 2019554844 A JP2019554844 A JP 2019554844A JP 2019554844 A JP2019554844 A JP 2019554844A JP 6861843 B2 JP6861843 B2 JP 6861843B2
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- VMCRDONCOBHEHW-UHFFFAOYSA-N [2,6-bis(2,6-dimethylphenyl)phenyl]phosphane Chemical compound CC1=CC=CC(C)=C1C1=CC=CC(C=2C(=CC=CC=2C)C)=C1P VMCRDONCOBHEHW-UHFFFAOYSA-N 0.000 claims description 2
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Description
前記(B)成分は、10〜50重量%のスチレン構造を含有する、数平均分子量が500〜10000のオレフィン樹脂から選ばれ、且つ前記オレフィン樹脂の分子中には1、2位に付加されたブタジエン構造を含有する。
ビニルベンゼン0.481モル(68.4mL)、エチルビニルベンゼン0.0362モル(5.16mL)、1−クロロビニルベンゼン(40mmol)のジクロロエタン溶液(濃度:0.634mmol/mL)63mL、臭化テトラ−n−ブチルアンモニウム(1.5mmol)のジクロロエタン溶液(濃度:0.135mmol/mL)11mL、およびジクロロエタン500mLを1000mLのフラスコに投入した。70℃で、1.5mmolのSnCl4のジクロロエタン溶液(濃度:0.068mmol/mL)1.5mLを添加し、反応時間が1時間である。窒素ガスで発泡が行われた少量のメタノールを用いて重合反応を終止させた後、室温で反応混合液を大量のメタノールに投入して重合体を析出させ、得られた重合体をメタノールで洗浄し、濾過、乾燥、秤量を行って合計54.6gの共重合体VOD−A(収率49.8wt%)を得た。
ビニルベンゼン0.481モル(68mL)、エチルビニルベンゼン0.362モル(52mL)、1−クロロビニルベンゼン(30mmol)のジクロロエタン溶液(濃度:0.634mmol/mL)47mL、テトラ−n−ブチルアンモニウムクロリド(2.25mmol)のジクロロエタン溶液(濃度:0.035mmol/mL)65mL、およびジクロロエタン500mLを1000mLのフラスコに投入した。70℃で、1.5mmolのSnCl4のジクロロエタン溶液(濃度:0.068mmol/mL)を22mL添加し、反応時間が1時間である。窒素ガスで発泡が行われた少量のメタノールを用いて重合反応を終止させた後、室温で反応混合液を大量のメタノールに投入して重合体を析出させ、得られた重合体をメタノールで洗浄し、濾過、乾燥、秤量を行って合計67.4gの共重合体VOD−B(収率61.4wt%)を得た。
ビニルベンゼン0.0481モル(6.84mL)、エチルビニルベンゼン0.0362モル(5.16mL)、下記一般式(a5)で表されるコバルト系連鎖移動剤12.0mgおよびテトラヒドロフラン150mlを300mlのフラスコに投入した。50℃で、2,2’−アゾビス(2,4−ジメチルバレロニトリル)をさらに添加して72時間反応させた。室温で反応混合液を大量のメタノールに投入して重合体を析出させ、得られた重合体をメタノールで洗浄し、濾過、乾燥、秤量を行って合計3.15gの共重合体VOD−C(収率28.7wt%)を得た。
80.0重量部の多官能ビニル芳香族共重合体VOD−A、20.0重量部のスチレン−ブタジエン共重合体Ricon100(Sartomer社製、スチレンの含有量が25%である)、3.0重量部のラジカル開始剤DCP、25重量部の臭素含有難燃剤BT−93W、60重量部のシリカ微粉S0−C2をトルエン溶剤に溶解させ、適切な粘度までに調整した。NE−ガラス繊維布(Nittobo、型番2116NE)を用いて樹脂接着剤に浸潤させ、クランク軸によって適切な単位重量までに制御し、オーブンに乾燥させ、トルエン溶剤を除去して2116プリプレグを調製した。それぞれ6枚の2116プリプレグおよび12枚の2116プリプレグを積層し、上下両面に1OZ厚みの銅箔を配置し、ラミネーターにおいて120minの真空積層硬化を行い、硬化圧力が50kg/cm2であり、硬化温度が200℃であり、2種類の厚み(6*2116−0.76mmの板は、綜合性能のテストに用いられ、12*2116−1.52mmの板は、機械的性能のテストに用いられる)の高速配線基板を製造した。
実施例1における製造方法と同様であるが、多官能ビニル芳香族共重合体VOD−Aとスチレン−ブタジエン共重合体Ricon100の配合比は、元の重量比80:20から50:50に変更した。
実施例1における製造方法と同様であるが、オレフィン樹脂の成分は、スチレン−ブタジエン共重合体Ricon181(Sartomer社製、スチレンの含有量が28%である)で置換された。製造された銅箔基板の物性をテストし、その結果を表2に示す。
実施例1における製造方法と同様であるが、オレフィン樹脂の成分は、スチレン−ブタジエン−ジビニルベンゼン共重合体Ricon250(Sartomer社製、スチレンの含有量が35%である)で置換された。製造された銅箔基板の物性をテストし、その結果を表2に示す。
実施例4における製造方法と同様であるが、多官能ビニル芳香族共重合体VOD−Aとスチレン−ブタジエン−ジビニルベンゼン共重合体Ricon250の配合比は、元の従来比80:20から50:50に変更した。製造された銅箔基板の物性をテストし、その結果を表2に示す。
実施例1における製造方法と同様であるが、多官能ビニル芳香族共重合体VOD−Aとスチレン−ブタジエン共重合体Ricon100の配合比は、元の重量比80:20から13:87に変更した。製造された銅箔基板の物性をテストし、その結果を表2に示す。
実施例1における製造方法と同様であるが、多官能ビニル芳香族共重合体VOD−Aとスチレン−ブタジエン共重合体Ricon100の配合比は、元の重量比80:20から93:7に変更した。製造された銅箔基板の物性をテストし、その結果を表2に示す。
実施例1における製造方法と同様であるが、多官能ビニル芳香族共重合体VOD−Aは、多官能ビニル芳香族共重合体VOD−Bで置換された。製造された銅箔基板の物性をテストし、その結果を表2に示す。
100重量部の多官能ビニル芳香族共重合体VOD−A、3.0重量部のラジカル開始剤DCP、25重量部の臭素含有難燃剤BT−93W、60重量部のシリカ微粉S0−C2をトルエン溶剤に溶解させ、適切な粘度までに調整した。NE−ガラス繊維布(Nittobo、型番2116NE)を用いて樹脂接着剤に浸潤させ、クランク軸によって適切な単位重量までに制御し、オーブンに乾燥させ、トルエン溶剤を除去して2116プリプレグを調製した。それぞれ6枚の2116プリプレグおよび12枚の2116プリプレグを積層し、上下両面に1OZ厚みの銅箔を配置し、ラミネーターにおいて120minの真空積層硬化を行い、硬化圧力が50kg/cm2であり、硬化温度が200℃であり、2種類の厚み(6*2116−0.76mmの板は、綜合性能のテストに用いられ、12*2116−1.52mmの板は、機械的性能のテストに用いられる)の高速配線基板を製造した。製造された銅箔基板の物性をテストし、その結果を表3に示す。
80.0重量部の多官能ビニル芳香族共重合体VOD−C、20.0重量部のスチレン−ブタジエン共重合体Ricon100(Sartomer社製、スチレンの含有量が25%である)、3.0重量部のラジカル開始剤DCP、25重量部の臭素含有難燃剤BT−93W、60重量部のシリカ微粉S0−C2をテトラヒドロフランとトルエンの混合溶剤に溶解させ、適切な粘度までに調整した。NE−ガラス繊維布(Nittobo、型番2116NE)を用いて樹脂接着剤に浸潤させ、クランク軸によって適切な単位重量までに制御し、オーブンに乾燥させ、トルエン溶剤を除去して2116プリプレグを調製した。それぞれ6枚の2116プリプレグおよび12枚の2116プリプレグを積層し、上下両面に1OZ厚みの銅箔を配置し、ラミネーターにおいて120minの真空積層硬化を行い、硬化圧力が50kg/cm2であり、硬化温度が200℃であり、2種類の厚み(6*2116−0.76mmの板は、綜合性能のテストに用いられ、12*2116−1.52mmの板は、機械的性能のテストに用いられる)の高速配線基板を製造した。製造された銅箔基板の物性をテストし、その結果を表3に示す。
48重量部の多官能ビニル芳香族共重合体VOD−A、12重量部のビニル変性ポリフェニレンエーテル樹脂OPE−2ST−1、40重量部の水素化スチレンブタジエンブロック共重合体H1041、3.0重量部のラジカル開始剤DCP、25重量部の臭素含有難燃剤BT−93W、60重量部のシリカ微粉S0−C2をトルエン溶剤に溶解させ、適切な粘度までに調整した。NE−ガラス繊維布(Nittobo、型番2116NE)を用いて樹脂接着剤に浸潤させ、クランク軸によって適切な単位重量までに制御し、オーブンに乾燥させ、トルエン溶剤を除去して2116プリプレグを調製した。それぞれ6枚の2116プリプレグおよび12枚の2116プリプレグを積層し、上下両面に1OZ厚みの銅箔を配置し、ラミネーターにおいて120minの真空積層硬化を行い、硬化圧力が50kg/cm2であり、硬化温度が200℃であり、2種類の厚み(6*2116−0.76mmの板は、綜合性能のテストに用いられ、12*2116−1.52mmの板は、機械的性能のテストに用いられる)の高速配線基板を製造した。製造された銅箔基板の物性をテストし、その結果を表3に示す。
80重量部の多官能ビニル芳香族共重合体VOD−A、20重量部の(メタ)アクリロイル末端のかご型シルセスキオキサンA、3.0重量部のラジカル開始剤DCP、25重量部の臭素含有難燃剤BT−93W、60重量部のシリカ微粉S0−C2をトルエン溶剤に溶解させ、適切な粘度までに調整した。NE−ガラス繊維布(Nittobo、型番2116NE)を用いて樹脂接着剤に浸潤させ、クランク軸によって適切な単位重量までに制御し、オーブンに乾燥させ、トルエン溶剤を除去して2116プリプレグを調製した。それぞれ6枚の2116プリプレグおよび12枚の2116プリプレグを積層し、上下両面に1OZ厚みの銅箔を配置し、ラミネーターにおいて120minの真空積層硬化を行い、硬化圧力が50kg/cm2であり、硬化温度が200℃であり、2種類の厚み(6*2116−0.76mmの板は、綜合性能のテストに用いられ、12*2116−1.52mmの板は、機械的性能のテストに用いられる)の高速配線基板を製造した。製造された銅箔基板の物性をテストし、その結果を表3に示す。
80.0重量部の多官能ビニル芳香族共重合体VOD−A、20.0重量部のスチレン−ブタジエン共重合体D4272(Kraton社製、スチレンの含有量が53%である)、3.0重量部のラジカル開始剤DCP、25重量部の臭素含有難燃剤BT−93W、60重量部のシリカ微粉S0−C2をトルエン溶剤に溶解させ、適切な粘度までに調整した。NE−ガラス繊維布(Nittobo、型番2116NE)を用いて樹脂接着剤に浸潤させ、クランク軸によって適切な単位重量までに制御し、オーブンに乾燥させ、トルエン溶剤を除去して2116プリプレグを調製した。それぞれ6枚の2116プリプレグおよび12枚の2116プリプレグを積層し、上下両面に1OZ厚みの銅箔を配置し、ラミネーターにおいて120minの真空積層硬化を行い、硬化圧力が50kg/cm2であり、硬化温度が200℃であり、2種類の厚み(6*2116−0.76mmの板は、綜合性能のテストに用いられ、12*2116−1.52mmの板は、機械的性能のテストに用いられる)の高速配線基板を製造した。製造された銅箔基板の物性をテストし、その結果を表3に示す。
比較例5における製造方法と同様であるが、オレフィン樹脂の成分は、無水マレイン化ポリブタジエンRicon130MA8(Sartomer社製、スチレンの含有量が35%である)で置換された。製造された銅箔基板の物性をテストし、その結果を表3に示す。
表2および表3における物性データ照合から分かるように、比較例1において、多官能ビニル芳香族共重合体VOD−Aを用いて自己硬化した後、基材のガラス転移温度は、高く、電気的性能がよく、吸水率が低いが、その強靭性が極めて悪い。比較例2において、多官能ビニル芳香族共重合体VOD−Cを用いることにより、当該共重合体中に、一般式(a1)および(a2)で表される構造単位の合計量に対して、一般式(a1)で表される構造単位のモル分率が0.25、すなわち(a1)/[(a1)+(a2)]=0.25である場合、基材の耐熱性が低下すると共に、強靭性が悪い。比較例3において、水素化スチレンブタジエンブロック共重合体を添加することにより、基材の強靭性が改善されるが、ガラス転移温度が著しく低下し、分層爆裂が現れ、耐湿耐熱性が悪い。比較例4において、(メタ)アクリロイル末端のかご型シルセスキオキサンAを架橋剤として導入することにより、その極性が大きいので、誘電性能が悪い。比較例5において、用いられるスチレン−ブタジエン共重合体におけるスチレンの含有量が50%より大きいことに起因して、基材の強靭性が著しく低下する。比較例6において、無水マレイン化ポリブタジエンRicon130MA8を用いることにより、このようなポリオレフィン樹脂が極性構造を有するため、製造した基材の誘電性能が悪くなり、強靭性も低下する。実施例1〜8において、オレフィン樹脂(スチレン−ブタジエン共重合体)を多官能ビニル芳香族共重合体VOD−A/VOD−Bとして用いることにより、硬化された基材は、良好な強靭性を有し、その高いガラス転移温度、低い吸水率、優れた誘電特性および耐湿耐熱性を保持した。
Claims (14)
- 1枚または少なくとも2枚の積層されたプリプレグ、および積層されたプリプレグの一方側または両側に位置する金属箔を含む金属箔張積層板であって、
前記プリプレグは、基材と、含浸し乾燥した後に基材に付着された熱硬化性樹脂組成物とを含み、前記金属箔は、銅箔であり、
前記熱硬化性樹脂組成物は、(A)成分と、(B)成分と、(C)成分と、フィラーと、難燃剤とで構成される、ことを特徴とする金属箔張積層板。
(前記(A)成分は、溶剤可溶性の多官能ビニル芳香族共重合体であり、当該共重合体は、ジビニル芳香族化合物(a)およびエチルビニル芳香族化合物(b)を含む単量体に由来する構造単位を有する多官能ビニル芳香族共重合体であり、20モル%以上の、ジビニル芳香族化合物(a)に由来する繰り返し単位を含有し、且つ下記式(a1)および(a2)で表されるジビニル芳香族化合物(a)に由来するビニル基を含有する構造単位のモル分率が(a1)/[(a1)+(a2)]≧0.5を満たし、且つゲル浸透クロマトグラフィーで測定されたポリスチレン換算の数平均分子量Mnが600〜30000であり、重量平均分子量Mwの数平均分子量Mnに対する比Mw/Mnが20.0以下であり、
前記(B)成分は、10〜50重量%のスチレン構造を含有する、数平均分子量が500〜10000のオレフィン樹脂から選ばれ、且つ前記オレフィン樹脂の分子中には1、2位に付加されたブタジエン構造を含有し、前記オレフィン樹脂の分子中の1、2位に付加されたブタジエン含有量が20重量%以上であり、
前記熱硬化性樹脂組成物において、(A)成分および(B)成分の合計に対して、(A)成分の配合量が13〜93wt%であり、(B)成分の配合量が7〜87wt%であり、
前記(C)成分は、(A)成分+(B)成分を100重量部として、(C)成分の用量が0.1〜10重量部である開始剤であり、
前記フィラーは、有機フィラーおよび/または無機フィラーを含み、
前記難燃剤は、臭素含有難燃剤またはハロゲンフリー難燃剤であり、
前記熱硬化性樹脂組成物の樹脂成分に極性のヒドロキシ基が含まず、且つ硬化加工過程において、二次ヒドロキシ基などの極性基を生成しない。) - 前記オレフィン樹脂は、ブタジエン−スチレン共重合体および/またはブタジエン−スチレン−ジビニルベンゼン共重合体である、ことを特徴とする請求項1に記載の金属箔張積層板。
- 前記可溶性の多官能ビニル芳香族共重合体の数平均分子量Mnが600〜10000である、ことを特徴とする請求項1又は2に記載の金属箔張積層板。
- 前記可溶性の多官能ビニル芳香族共重合体の数平均分子量分布Mw/Mnの値が15以下である、ことを特徴とする請求項1又は2に記載の金属箔張積層板。
- 前記可溶性の多官能ビニル芳香族共重合体の金属イオン含有量は、各金属イオン含有量の和が、500ppm以下である、ことを特徴とする請求項1または2に記載の金属箔張積層板。
- (A)成分は、以下のような可溶性の多官能ビニル芳香族共重合体であり、すなわち、多官能ビニル芳香族共重合体において、エチルビニル芳香族化合物(b)以外のモノビニル芳香族化合物(c)に由来する構造単位を含有する、ことを特徴とする請求項1〜6のいずれか一項に記載の金属箔張積層板。
- 前記(C)成分としての開始剤の半減期温度t1/2が130℃以上であり、前記開始剤がラジカル開始剤である、ことを特徴とする請求項1に記載の金属箔張積層板。
- 前記開始剤は、ジクミルパーオキサイド、tert−ブチルベンゾイルペルオキシド、2,5−ビス(2−エチルヘキサノイルペルオキシ)−2,5−ジメチルヘキサン、ジ−(tert−ブチルペルオキシイソプロピル)ベンゼン、過酸化(2,4−ジクロロベンゾイル)、2,5−ジメチル−2,5−ビス(tert−ブチルペルオキシ)ヘキサン、tert−ブチルペルオキシ−2−エチルヘキシルカーボネート、2,5−ジメチル−2,5−ビス(tert−ブチルペルオキシ)−3−ヘキシン、ブチル−4,4−ビス(t−ブチルパーオキシ)バレレート、1,1−ビス(tert−ブチルペルオキシ)−3,3,5−トリメチルシクロヘキサン、3,3,5,7,7−ペンタメチル−1,2,4−トリオキセパン、ジ−tert−ブチルペルオキシドまたはtert−ブチルペルオキシクメンから選ばれる1種または少なくとも2種の組合せである、ことを特徴とする請求項8に記載の金属箔張積層板。
- 前記無機フィラーは、結晶型シリカ、溶融シリカ、球形シリカ、中空シリカ、ガラス粉末、窒化アルミニウム、窒化ホウ素、炭化ケイ素、炭化ケイ素アルミニウム、水酸化アルミニウム、水酸化マグネシウム、二酸化チタン、チタン酸バリウム、チタン酸バリウム、酸化亜鉛、酸化ジルコニウム、酸化アルミニウム、酸化ベリリウム、酸化マグネシウム、硫酸バリウム、タルク、粘土、ケイ酸カルシウム、炭酸カルシウムまたはマイカから選ばれる1種または少なくとも2種の組合せであり、
前記有機フィラーは、ポリテトラフルオロエチレン粉末、ポリフェニレンスルフィド、ポリエーテルイミド、ポリフェニレンエーテルまたはポリエーテルスルホン粉末から選ばれる1種または少なくとも2種の組合せである、ことを特徴とする請求項1に記載の金属箔張積層板。 - 前記臭素含有難燃剤は、デカブロモジフェニルエーテル、デカブロモジフェニルエタン、エチレンビステトラブロモフタルイミドまたは臭素化ポリカーボネートから選ばれる1種または少なくとも2種の組合せであり、
前記ハロゲンフリー難燃剤は、リン含有ハロゲンフリー難燃剤、窒素含有ハロゲンフリー難燃剤およびケイ素含有ハロゲンフリー難燃剤から選ばれる1種または少なくとも2種の組合せである、ことを特徴とする請求項1に記載の金属箔張積層板。 - 前記ハロゲンフリー難燃剤は、トリス(2,6−ジメチルフェニル)ホスフィン、10−(2,5−ジヒドロキシフェニル)−9,10−ジヒドロ−9−オキサ−10−ホスファフェナントレン−10−オキシド、2,6−ビス(2,6−ジメチルフェニル)ホスフィノベンゼンまたは10−フェニル−9,10−ジヒドロ−9−オキサ−10−ホスファフェナントレン−10−オキシド、フェノキシホスフィンシアン化合物、リン酸エステルまたはポリリン酸エステルから選ばれる1種または少なくとも2種の組合せである、ことを特徴とする請求項11に記載の金属箔張積層板。
- (A)成分+(B)成分を100重量部として、前記難燃剤の用量が5〜80重量部である、ことを特徴とする請求項1に記載の金属箔張積層板。
- 前記基材は、有機繊維、炭素繊維または無機繊維により製造された織物または不織物である、ことを特徴とする請求項1に記載の金属箔張積層板。
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JP2009040934A (ja) * | 2007-08-10 | 2009-02-26 | Nippon Steel Chem Co Ltd | 硬化性樹脂組成物 |
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TWI706963B (zh) * | 2015-12-28 | 2020-10-11 | 日商日鐵化學材料股份有限公司 | 可溶性多官能乙烯基芳香族共聚合物、其製造方法、硬化性組成物及其應用 |
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2017
- 2017-08-04 CN CN201710662027.0A patent/CN109385021A/zh active Pending
- 2017-10-19 EP EP17920511.7A patent/EP3663348A4/en not_active Withdrawn
- 2017-10-19 US US16/632,005 patent/US20210070980A1/en not_active Abandoned
- 2017-10-19 WO PCT/CN2017/106830 patent/WO2019024255A1/zh unknown
- 2017-10-19 KR KR1020207000065A patent/KR20200015930A/ko not_active Application Discontinuation
- 2017-10-19 JP JP2019554844A patent/JP6861843B2/ja active Active
- 2017-11-21 TW TW106140387A patent/TWI658083B/zh active
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TWI658083B (zh) | 2019-05-01 |
EP3663348A1 (en) | 2020-06-10 |
JP2020515701A (ja) | 2020-05-28 |
WO2019024255A1 (zh) | 2019-02-07 |
EP3663348A4 (en) | 2021-04-28 |
US20210070980A1 (en) | 2021-03-11 |
TW201910412A (zh) | 2019-03-16 |
CN109385021A (zh) | 2019-02-26 |
KR20200015930A (ko) | 2020-02-13 |
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