CN103080144B - 酯化物的制造方法 - Google Patents

酯化物的制造方法 Download PDF

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CN103080144B
CN103080144B CN201180025950.4A CN201180025950A CN103080144B CN 103080144 B CN103080144 B CN 103080144B CN 201180025950 A CN201180025950 A CN 201180025950A CN 103080144 B CN103080144 B CN 103080144B
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carbonatoms
alkene
carboxylate
alcohol
reaction mixture
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CN103080144A (zh
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田部井纯一
曾根嘉久
村田清贵
高桥航
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Air Water Inc
Sumitomo Bakelite Co Ltd
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Sumitomo Bakelite Co Ltd
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Abstract

根据本发明，提供一种酯化物的制造方法，包括：将碳原子数为5～80的1-烯烃与马来酸酐共聚而得到共聚物的工序，使上述共聚物与碳原子数为5～25的醇在三氟甲磺酸的存在下发生酯化反应而得到含有含选自式（c）～（f）中的至少一个重复单元的酯化物的反应混合物的工序；其中，式（c）～（f）中，R表示碳原子数为3～78的脂肪族烃基，R2表示碳原子数为5～25的烃基，m表示上述1-烯烃（X）与上述马来酸酐（Y）的共聚摩尔比X/Y、且为1/2～10/1，n为1以上的整数。

Description

酯化物的制造方法
技术领域
本发明涉及酯化物的制造方法。更详细而言，涉及用于在半导体元件的密封材料中使用的酯化物的制造方法。
背景技术
半导体元件的密封材料中，使用酯化物作为用于改善连续成型性和耐回焊性的添加剂。这样的酯化物，可由酸酐与1-烯烃的聚合物和醇合成(专利文献1)。
由于酸酐与1-烯烃的聚合物和醇反应而得到酯化物的反应迟缓，因此需要催化剂。专利文献1中使用对甲苯磺酸作为催化剂，进行该反应。但是，这样的磺酸有时残留在得到的反应生成物中。将这样的残留有对甲苯磺酸的酯化物用作半导体元件的密封材料时，成为半导体元件的绝缘不良的原因。因此，为了将用专利文献1的方法得到的酯化物用作半导体元件的密封材料，需要将残留的磺酸类减少至不发生半导体元件的绝缘不良等不良情况的水平。磺酸类可通过对反应生成物进行清洗而除去，但利用清洗的除去，其操作繁琐，并且磺酸类的除去效率也不高。另外，进一步进行过度清洗的情况下，有时能够将半导体元件密封所需要的有助于耐回焊性、脱模性的低分子量的酯化物、1-烯烃除去。
专利文献1:日本特愿2010-122191
发明内容
本发明鉴于上述情况而完成，提供一种精制效率优异的作为半导体元件的密封材料有用的酯化物的制造方法。
根据本发明，能够提供一种酯化物的制造方法，其中，包括：将碳原子数为5～80的1-烯烃与马来酸酐共聚而得到共聚物的工序，使上述共聚物与碳原子数为5～25的醇在三氟甲磺酸的存在下发生酯化反应而得到含有包含选自式(c)～(f)中的至少一个重复单元的酯化物的反应混合物的工序。
(式(c)～(f)中，R表示碳原子数为3～78的脂肪族烃基，R2表示碳原子数为5～25的烃基，m表示上述1-烯烃(X)与上述马来酸酐(Y)的共聚摩尔比X/Y、且为1/2～10/1，n为1以上的整数。)
根据本发明的一个实施方式，上述方法还包括在得到含有酯化物的反应混合物的上述工序后，通过减压处理除去游离三氟甲磺酸的工序。
根据本发明的一个实施方式，上述方法中，上述反应混合物含有上述碳原子数为5～80的1-烯烃。
根据本发明的一个实施方式，上述方法中，利用GPC测定的上述反应混合物中的上述碳原子数为5～80的1-烯烃的含有比例为8面积％～20面积％。
根据本发明的一个实施方式，上述方法中，上述1-烯烃是碳原子数为28～60的1-烯烃。
根据本发明的一个实施方式，上述方法中，上述醇是硬脂醇。
根据本发明的一个实施方式，上述方法中，相对于上述共聚物与上述碳原子数为5～25的醇的总质量，上述三氟甲磺酸为100ppm～1000ppm的量。
根据本发明，在酸酐与1-烯烃的聚合物和醇的反应中，通过使用三氟甲磺酸作为催化剂，从而能够得到磺酸成分的含量减少了的反应混合物，能够实现酯化物的高效地制造方法。即，由于无需除去磺酸成分，因此不会伴有因磺酸成分的除去引起的操作效率的降低，能够高效地得到酯化物。另外，可根据需要，通过减压蒸馏除去三氟甲磺酸。因此，能够得到磺酸成分的含量被充分减少的反应混合物。另外，将这样得到的酯化物用作半导体元件的密封材料的情况下，能够减少因磺酸成分引起的半导体元件的绝缘不良等不良情况的发生。
具体实施方式
以下，对本发明的酯化物的制造方法进行说明。
本发明的酯化物的制造方法包括以下工序。
(a)将碳原子数为5～80的1-烯烃与马来酸酐共聚而得到共聚物的工序；以及
(b)使工序(a)中得到的共聚物与碳原子数为5～25的醇在三氟甲磺酸的存在下发生酯化反应，得到含有包含选自式(c)～(f)中的至少一个重复单元的酯化物的反应混合物的工序。
(式(c)～(f)中，R表示碳原子数为3～78的脂肪族烃基，R2表示碳原子数为5～25的烃基，m表示上述1-烯烃(X)与上述马来酸酐(Y)的共聚摩尔比X/Y、且为1/2～10/1，n为1以上的整数。)
作为可在上述工序(a)中使用的碳原子数为5～80的1-烯烃，例如可举出1-戊烯、1-己烯、1-辛烯、1-癸烯、1-十二碳烯、1-十八碳烯、1-二十碳烯、1-二十二碳烯、1-四十碳烯、1-六十碳烯、1-二十八碳烯、1-三十碳烯、1-三十一碳烯、1-三十二碳烯、1-三十三碳烯、1-三十四碳烯、1-三十五碳烯、1-三十六碳烯、1-四十碳烯、1-四十一碳烯、1-四十二碳烯、1-四十三碳烯，1-四十四碳烯、1-五十碳烯、1-五十一碳烯、1-五十二碳烯、1-五十三碳烯、1-五十五碳烯、1-六十碳烯、1-七十碳烯、1-八十碳烯等直链型1-烯烃，3-甲基-1-三十碳烯、3,4-二甲基-三十碳烯、3-甲基-1-四十碳烯、3,4-二甲基-四十碳烯等支链型1-烯烃等，可以单独使用这些，也可以组合2种以上使用。
对于1-烯烃的碳原子数，使用得到的酯化合物作为半导体元件的密封材料时，从对于半导体元件所具备的引线框的粘合性的观点出发，更优选碳原子数为10～70，从脱模性的观点出发，进一步优选碳原子数为28～60。
作为上述工序(a)中得到的碳原子数为5～80的1-烯烃与马来酸酐的共聚物，例如可举出具有以式(9)和式(10)表示的结构的化合物，作为市售品，可举出使用了1-二十八碳烯、1-三十碳烯、1-四十碳烯、1-五十碳烯、1-六十碳烯等作为原料的DIACARNA(注册商标)30(三菱化学株式会社制商品名)。
上述通式(9)和(10)中的R表示碳原子数为3～78的脂肪族烃基，n为1以上的整数。m表示1-烯烃与马来酸酐的共聚比，没有特别限制，但将1-烯烃设为X摩尔，马来酸酐设为Y摩尔时，X/Y，即，m为1/2～10/1，优选为1/2～5/1，更优选为1/2～2/1，进一步优选为大致等摩尔程度的1/1左右。
作为1-烯烃与马来酸酐的共聚物的制造方法，没有特别限制，可使用使原材料反应等的一般共聚方法。反应中可以使用能够将1-烯烃与马来酸酐溶解的有机溶剂等。作为有机溶剂没有特别限制，优选为甲苯，也可使用芳香族系溶剂、醚系溶剂、卤素系溶剂等。反应温度根据使用的有机溶剂的种类不同而异，但从反应性、生产率的观点出发，优选为50～200℃，更优选为100～150℃。如果能够得到共聚物，则反应时间没有特别限制，从生产率的观点出发，优选为1～30小时，更优选为2～15小时，进一步优选为4～10小时。反应结束后，可根据需要在加热减压下等除去未反应成分、溶剂等。优选其条件如下：温度为100～220℃，更优选为120～180℃，压力为13.3×103Pa以下，更优选为8×103Pa以下，时间为0.5～10小时。另外，根据需要，可以向反应中加入偶氮二异丁腈(AIBN)、过氧化苯甲酰(BPO)等自由基聚合系引发剂。
使用碳原子数为5～25的醇，将工序(a)中得到的共聚物在工序(b)中在三氟甲磺酸的存在下酯化。
作为可在上述工序(b)中使用的碳原子数为5～25的醇，例如可举出戊醇、己醇、辛醇、癸醇、月桂醇、肉豆蔻醇、鲸蜡醇、硬脂醇、二十烷醇、山嵛醇、2-甲基-癸烷-1-醇、2-乙基-癸烷-1-醇、2-己基-辛烷-1-醇等直链型或支链型的脂肪族饱和醇，己烯醇、2-己烯-1-醇、1-己烯-3-醇、戊烯醇、2-甲基-1-戊烯醇等直链型或者支链型的脂肪族不饱和醇等，可以单独使用这些也可以组合使用2种以上。这些醇中，从将得到的酯化物作为半导体元件的密封材料使用时的脱模性的观点出发，优选为碳原子数为10～25的直链型醇，从连续成型性的观点出发，更优选碳原子数为15～20的直链型脂肪族饱和醇。如果醇的碳原子数低于上述下限值，则连续成型性(脱模性)差，如果超过上述上限值，则有对于半导体元件的铜制引线框的粘合性下降的趋势。
为了发挥该性能，优选相对于共聚物与醇的总质量，三氟甲磺酸的量为100ppm～1000ppm的量。如果低于上述下限值，则不能充分发挥作为酯化催化剂的功能，如果超过上述上限值，则有时得到的酯化物被氧化。使用酯化物的氧化物作为半导体元件的密封材料时，有连续成型性降低的趋势。
工序(a)中得到的共聚物与碳原子数为5～25的醇的摩尔比没有特别限制，可进行任意设定，但通过调整该反应摩尔比，从而能够控制酯化物的亲水性的程度，因此优选与使用的半导体密封材料相匹配地进行适当设定。反应可使用能够溶解1-烯烃和马来酸酐的有机溶剂等。作为有机溶剂没有特别限制，优选为甲苯，也可使用芳香族系溶剂、醚系溶剂、卤素系溶剂等。反应温度也根据使用的有机溶剂的种类不同而异，从反应性、生产率的观点出发，优选为50～200℃，更优选为120～170℃。对于反应时间，只要能够得到共聚物，就没有特别限制，从生产率的观点出发，优选为1～30小时，更优选为2～30小时，进一步优选为4～28小时。反应结束后，根据需要可在加热减压下等除去未反应成分、溶剂等。优选其条件如下：温度为100～220℃，更优选为120～180℃，压力为13.3×103Pa以下，更优选为8×103Pa以下，时间为0.5～10小时。
使用上述碳原子数为5～25的醇将1-烯烃与马来酸酐的共聚物酯化而得到的酯化物包含选自式(c)～(f)中的至少一个重复单元。
式(c)～(f)中，R表示碳原子数为3～78的脂肪族烃基，R2表示碳原子数为5～25的烃基，m表示上述1-烯烃(X)与上述马来酸酐(Y)的共聚摩尔比X/Y、且为1/2～10/1，n为1以上的整数。
本发明的酯化物可举出(1)主链骨架中单独含有式(c)～(f)中任1种的化合物，(2)主链骨架中无规地含有、规则地含有或嵌段状地含有式(c)～(f)中任2种以上的化合物等，可以单独为它们，也可以为2种以上的混合物。
共聚物与醇的酯化反应的反应收率优选为70摩尔％以上，更优选为80摩尔％以上，进一步优选为90％摩尔以上。
含有工序(b)中得到的酯化物的反应混合物可以含有工序(a)中未反应而存在的1-烯烃。反应混合物中的1-烯烃的含有比例通过GPC进行测定时，优选为8质量％～20质量％。如果含有比例为上述下限值以上，则能够得到提高脱模性的效果。如果含有比例为上述上限值以下，则引起粘合性下降等的可能性小。
优选本发明的方法中得到的酯化物的数均分子量为2000～10000。如果为上述范围，则使用酯化物作为半导体的密封材料时，能够实现兼得对于半导体元件的铜制引线框的粘合性和脱模性。
将1-烯烃与马来酸酐的共聚物在三氟甲磺酸的存在下用醇酯化而成的化合物的配合量没有特别限制，相对于环氧树脂100质量份，优选为0.5质量份～10质量份，更优选为1质量份～5质量份。如果配合量低于上述下限值，则有脱模性降低的趋势，如果超过上述上限值，则有对于进行了氧化的铜制引线框的粘合性不充分的趋势。
本发明中，工序(b)后，根据需要，可以通过减压处理除去工序(b)中得到的反应混合物中的游离三氟甲磺酸。通过上述方法，能够减少三氟甲磺酸的含量，因此，使用含有工序(b)中得到的酯化物的反应性生成物作为半导体密封材料时，对于半导体元件的铜制引线框的粘合性和脱模性良好。
实施例
以下，举出实施例对本发明进行详细说明，但本发明并不限定于这些实施例。
(合成例1)
将碳原子数为28～60的1-烯烃与马来酸酐的共聚物(DIACARNAR30，三菱化学株式会社制)100.0g、以及硬脂醇47.0g装入到300ml的4口可拆式烧瓶中，在70℃溶解后，添加10wt％三氟甲磺酸水溶液0.5g。将得到的反应混合物在150℃搅拌5小时。
其后，将液温冷却至120℃，在30Torr的减压下，减压蒸馏2小时，由此除去游离的三氟甲磺酸和水，得到144g的酯化物A。根据GPC测定结果，酯化物A中的1-烯烃含量为15质量％。另外酯化物A的硫含量为74ppm。
(合成例2)
将碳原子数为28～60的1-烯烃与马来酸酐的共聚物(DIACARNAR30，三菱化学株式会社制)100.0g、以及硬脂醇47.0g装入300ml的4口可拆式烧瓶中，在70℃溶解后，添加对甲苯磺酸一水合物1.5g。将得到的反应混合物在150℃下搅拌4小时。
其后，将液温冷却至80℃，在回流下用60分钟滴加丙酮131.7g。滴加后停止搅拌，在液温70℃下静置60分钟，则反应母液可拆成2层。除去含有未反应的硬脂醇和磺酸成分的上层丙酮层。将留下的下层在30Torr的减压下，在90℃进行减压馏去6小时，除去残留的丙酮，得到144g酯化物B。根据GPC测定结果，酯化物B中的1-烯烃含量为10质量％。另外酯化物B的硫含量为800ppm。
(合成例3)
将碳原子数为28～60的1-烯烃与马来酸酐的共聚物(DIACARNAR30，三菱化学株式会社制)100.0g、以及硬脂醇47.0g装入到安装有冷凝器的300ml的4口可拆式烧瓶，在70℃溶解后，添加对甲苯磺酸一水合物1.5g。将得到的反应混合物在150℃搅拌4小时。
其后，将液温冷却至80℃，在回流下用60分钟滴加丙酮131.7g。滴加后停止搅拌，在液温70℃下静置60分钟，则反应母液可拆成2层。除去含有未反应的硬脂醇和磺酸成分的上层丙酮层。进行3次该清洗操作后，将留下的下层在30Torr的减压下，在90℃进行减压馏去6小时，由此除去残留的丙酮，得到135g的酯化物C。根据GPC测定结果，酯化物C中的1-烯烃含量为7质量％。另外酯化物C的硫含量为400ppm。
(实施例1)
以表中所示的质量份配合上述合成例1中得到的酯化物A以及下表所示的成分，在混炼温度100℃、混炼时间30分钟的条件下进行双轴混炼，冷却后粉碎，制成树脂组合物。对得到的树脂组合物作为半导体密封材料的性能(连续成型性)进行评价。结果示于表1。
(比较例1～2)
以表中所示的质量份配合上述合成例2和3中得到的酯化物B和C、以及下表中所示的成分，在混炼温度100℃、混炼时间30分钟的条件下进行双轴混炼，冷却后粉碎，制成树脂组合物。对得到的树脂组合物作为半导体密封材料的性能(连续成型性)进行评价。结果示于表1。
对上述实施例和比较例中使用的各成分，在以下示出。
环氧树脂1：环氧当量185g/eq、熔点108℃的联苯型环氧树脂(JapanEpoxy株式会社制商品名EPIKOTE YX-4000K)
环氧树脂2：环氧当量237g/eq、软化点52℃的具有亚苯基骨架的苯酚芳烷型环氧树脂(日本化药制商品名NC2000)
酚醛树脂系固化剂1：羟基当量199g/eq、软化点64℃的具有亚联苯基骨架的苯酚芳烷型酚醛树脂(明和化成株式会社制商品名MEH-7851SS)
无机填充材料1：平均粒径10.8μm，比表面积5.1m2/g的球状熔融二氧化硅
固化促进剂1：三苯基膦与对苯醌的加成物
偶联剂1：γ-环氧丙氧基丙基三甲氧基硅烷(Chisso制商品名S510＝GPS-M)
着色剂1：炭黑(三菱化学株式会社制商品名Carbon#5)
连续成型性(通气口堵塞和模具污染)的测定方法如下。
使用低压传输自动成型机(第一精工(株)制，GP-ELF)，在模具温度175℃、注入压力9.8MPa、固化时间70秒的条件下，利用环氧树脂组合物将芯片等密封，得到80引脚四方扁平式封装(80pQFP；铜制引线框、封装外部尺寸：14mm×20mm×2mm厚，焊盘尺寸：6.5mm×6.5mm，芯片尺寸6.0mm×6.0mm×0.35mm厚)，将得到的80引脚四方扁平式封装进行连续成型400次(shot)。
对于通气口堵塞的评价，每50次为单位目视观察模具，由此确认有无通气口堵塞(树脂固化物在通气口(宽度0.5mm，厚度50μm)部固定而堵塞通气口的状态)，按以下4个等级进行评价。优选的顺序为A、B、C···的顺序，C等级以上则为可实用的范围。评价结果在下述示出。
A：至400次无问题
B：至300次发生通气口堵塞
C：至200次发生通气口堵塞
D：至100次发生通气口堵塞产生
对于模具污染，观察400次成型后的模具，由从浇口污染蔓延情况的程度，按以下5个等级进行评价。优选的顺序为A、B、C···的顺序，C等级以上则为可实用的范围。
A：无污染
B：污染蔓延为型腔表面的20面积％以下
C：污染蔓延超过型腔表面的20面积％且为40面积％以下
D：污染蔓延超过型腔表面的40面积％且为60面积％以下
E：污染蔓延超过型腔表面的60面积％
表1

Claims (6)

1.一种酯化物的制造方法，其中，包括：
将碳原子数为5～80的1-烯烃与马来酸酐共聚而得到共聚物的工序，
使所述共聚物与碳原子数为5～25的醇在三氟甲磺酸的存在下发生酯化反应，得到含有包含选自式(c)～(f)中的至少一个重复单元的酯化物的反应混合物的工序；
式(c)～(f)中，R表示碳原子数为3～78的脂肪族烃基，R2表示碳原子数为5～25的烃基，m表示所述1-烯烃(X)与所述马来酸酐(Y)的共聚摩尔比X/Y、且为1/2～10/1，n为1以上的整数。
2.根据权利要求1所述的方法，其中，还包括在得到含有酯化物的反应混合物的所述工序后，通过减压处理除去游离三氟甲磺酸的工序。
3.根据权利要求1所述的方法，其中，所述反应混合物含有所述碳原子数为5～80的1-烯烃。
4.根据权利要求3所述的方法，其中，利用GPC测定的所述反应混合物中的所述碳原子数为5～80的1-烯烃的含有比例为8质量％～20质量％。
5.根据权利要求1所述的方法，其中，所述醇为硬脂醇。
6.根据权利要求1所述的方法，其中，相对于所述共聚物与所述碳原子数为5～25的醇的总质量，所述三氟甲磺酸为100ppm～1000ppm的量。
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