JP5782434B2 - エステル化物の製造方法 - Google Patents
エステル化物の製造方法 Download PDFInfo
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- JP5782434B2 JP5782434B2 JP2012517139A JP2012517139A JP5782434B2 JP 5782434 B2 JP5782434 B2 JP 5782434B2 JP 2012517139 A JP2012517139 A JP 2012517139A JP 2012517139 A JP2012517139 A JP 2012517139A JP 5782434 B2 JP5782434 B2 JP 5782434B2
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Description
(式(c)〜(f)中、Rは炭素数3〜78の脂肪族炭化水素基を示し、R2は炭素数5〜25の炭化水素基を示し、mは、前記1−アルケン(X)と前記無水マレイン酸(Y)の共重合モル比X/Yを示し、1/2〜10/1であり、nは1以上の整数である。)
本発明のエステル化物の製造方法は、以下の工程を含む。
(a)炭素数5〜80の1−アルケンと無水マレイン酸とを共重合して共重合物を得る工程;および
(b)工程(a)で得られた共重合物と、炭素数5〜25のアルコールとを、トリフルオロメタンスルホン酸の存在下でエステル化反応させて、式(c)〜(f)から選択される少なくとも1つの繰り返し単位を含むエステル化物を含有する反応混合物を得る工程。
(式(c)〜(f)中、Rは炭素数3〜78の脂肪族炭化水素基を示し、R2は炭素数5〜25の炭化水素基を示し、mは、上記1−アルケン(X)と上記無水マレイン酸(Y)の共重合モル比X/Yを示し、1/2〜10/1であり、nは1以上の整数である。)
炭素数28〜60の1−アルケンと無水マレイン酸との共重合物(ダイヤカルナR30、三菱化学株式会社製)100.0g、およびステアリルアルコール47.0gを、300mlの4つ口セパラブルフラスコに仕込み、70℃で溶解させた後に、10wt%トリフルオロメタンスルホン酸水溶液0.5gを添加した。得られた反応混合物を150℃で5時間攪拌した。
その後、液温を120℃まで冷却して、30Torrの減圧下で、2時間減圧蒸留することにより、遊離のトリフルオロメタンスルホン酸と水を除去して、エステル化物Aを144g得た。GPC測定結果から、エステル化物A中の1−アルケン含有量は15質量%であった。またエステル化物Aの硫黄含有量は74ppmであった。
炭素数28〜60の1−アルケンと無水マレイン酸との共重合物(ダイヤカルナR30、三菱化学株式会社製)100.0g、およびステアリルアルコール47.0gを、300mlの4つ口セパラブルフラスコに仕込み、70℃で溶解させた後に、p−トルエンスルホン酸一水和物1.5gを添加した。得られた反応混合物を150℃で4時間攪拌した。
その後、液温を80℃まで冷却して、アセトン131.7gを還流下で60分間かけて滴下した。滴下後は攪拌を止め、液温70℃で60分間静置させると、反応母液が2層に分離した。未反応のステアリルアルコールおよびスルホン酸成分を含む上層のアセトン層は除去した。残る下層を30Torrの減圧下で、90℃で6時間減圧留去を行うことにより、残存するアセトンを除去して、エステル化物Bを144g得た。GPC測定結果から、エステル化物B中の1−アルケン含有量は10質量%であった。またエステル化物Bの硫黄含有量は800ppmであった。
炭素数28〜60の1−アルケンと無水マレイン酸との共重合物(ダイヤカルナR30、三菱化学株式会社製)100.0g、およびステアリルアルコール47.0gを、コンデンサーを装着した300mlの4つ口セパラブスフラスコに仕込み、70℃で溶解させた後に、p−トルエンスルホン酸一水和物1.5gを添加した。得られた反応混合物を150℃で4時間攪拌した。
その後、液温を80℃まで冷却して、アセトン131.7gを還流下で60分間かけて滴下した。滴下後は攪拌を止め、液温70℃で60分間静置させると、反応母液が2層に分離した。未反応のステアリルアルコールおよびスルホン酸成分を含む上層のアセトン層は除去した。この洗浄操作を3回行った後、残る下層を30Torrの減圧下で、90℃で6時間減圧留去を行うことにより、残存するアセトンを除去して、エステル化物Cを135g得た。GPC測定結果から、エステル化物C中の1−アルケン含有量は7質量%であった。またエステル化物Cの硫黄含有量は400ppmであった。
(実施例1)
上記合成例1で得られたエステル化物A、および以下の表に示す成分を、表に示す質量部で配合し、混練温度100℃、混練時間30分の条件で二軸混練して冷却後粉砕し、樹脂組成物を作製した。得られた樹脂組成物を、半導体封止材としての性能(連続成形性)について評価した。結果を表1に示す。
(比較例1〜2)
上記合成例2および3で得られたエステル化物BおよびC、および以下の表に示す成分を、表に示す質量部で配合し、混練温度100℃、混練時間30分の条件で二軸混練して冷却後粉砕し、樹脂組成物を作製した。得られた樹脂組成物を、半導体封止材としての性能(連続成形性)について評価した。結果を表1に示す。
エポキシ樹脂1:エポキシ当量185g/eq、融点108℃のビフェニル型エポキシ樹脂(ジャパンエポキシ株式会社製商品名エピコートYX−4000K)
エポキシ樹脂2:エポキシ当量237g/eq、軟化点52℃のフェニレン骨格を有するフェノールアラルキル型エポキシ樹脂(日本化薬製商品名NC2000)
フェノール樹脂系硬化剤1:水酸基当量199g/eq、軟化点64℃のビフェニレン骨格を有するフェノールアラルキル型フェノール樹脂(明和化成株式会社製商品名MEH−7851SS)
無機充填材1:平均粒径10.8μm、比表面積5.1m2/gの球状溶融シリカ
硬化促進剤1:トリフェニルホスフィンとp−ベンゾキノンとの付加物
カップリング剤1:γ−グリシドキシプロピルトリメトキシシラン(チッソ製商品名S510=GPS−M)
着色剤1:カーボンブラック(三菱化学株式会社製商品名カーボン#5)
低圧トランスファー自動成形機(第一精工(株)製、GP−ELF)を用いて、金型温度175℃、注入圧力9.8MPa、硬化時間70秒の条件で、エポキシ樹脂組成物によりチップなどを封止して80ピンクワッドフラットパッケージ(80pQFP;銅製リードフレーム、パッケージ外寸:14mm×20mm×2mm厚、パッドサイズ:6.5mm×6.5mm、チップサイズ6.0mm×6.0mm×0.35mm厚)を得る成形を、連続で400ショットまで行った。
エアベントブロックの評価については、50ショット毎に金型を目視により観察することで、エアベントブロック(エアベント(幅0.5mm、厚さ50μm)部に樹脂硬化物が固着してエアベントを塞いだ状態)の有無を確認し、次の4段階で評価した。好ましい順は、A、B、C・・・の順であるが、Cランク以上であれば実用可能範囲である。評価結果を下記に示した。
A:400ショットまで問題なし
B:300ショットまでにエアベントブロック発生
C:200ショットまでにエアベントブロック発生
D:100ショットまでにエアベントブロック発生
型汚れについては、400ショット成形後の金型を観察し、ゲート口からの汚れの広がり具合の程度から、次の5段階で評価した。好ましい順は、A、B、C・・・の順であるが、Cランク以上であれば実用可能範囲である。
A:汚れなし
B:汚れの広がりがキャビティ表面の20面積%以下
C:汚れの広がりがキャビティ表面の20面積%超〜40面積%以下
D:汚れの広がりがキャビティ表面の40面積%超〜60面積%以下
E:汚れの広がりがキャビティ表面の60面積%超
Claims (7)
- エステル化物を含有する反応混合物を得る前記工程の後に、遊離トリフルオロメタンスルホン酸を減圧処理により除去する工程をさらに含む、請求項1に記載の方法。
- 前記反応混合物が、前記炭素数5〜80の1−アルケンを含有する、請求項1に記載の方法。
- GPCにより測定される、前記反応混合物中の前記炭素数5〜80の1−アルケンの含有割合が、8質量%以上、20質量%以下である、請求項3に記載の方法。
- 前記1−アルケンが、炭素数28〜60の1−アルケンである、請求項1に記載の方法。
- 前記アルコールが、ステアリルアルコールである、請求項1に記載の方法。
- 前記トリフルオロメタンスルホン酸が、前記共重合物と前記炭素数5〜25のアルコールとの全質量に対し、100ppm以上、1000ppm以下の量である、請求項1に記載の方法。
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KR20130124175A (ko) | 2013-11-13 |
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TW201211138A (en) | 2012-03-16 |
SG185505A1 (en) | 2012-12-28 |
CN104250313A (zh) | 2014-12-31 |
CN103080144B (zh) | 2015-02-25 |
US20130059983A1 (en) | 2013-03-07 |
TWI520972B (zh) | 2016-02-11 |
KR20130113335A (ko) | 2013-10-15 |
US8648479B2 (en) | 2014-02-11 |
KR101835902B1 (ko) | 2018-03-07 |
US9070628B2 (en) | 2015-06-30 |
JPWO2011148628A1 (ja) | 2013-07-25 |
CN102918106A (zh) | 2013-02-06 |
KR101756499B1 (ko) | 2017-07-10 |
JPWO2011148627A1 (ja) | 2013-07-25 |
CN102918106B (zh) | 2015-09-16 |
US20130062748A1 (en) | 2013-03-14 |
TWI499629B (zh) | 2015-09-11 |
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