CN101379118B - 预成型料用环氧树脂固化性组合物 - Google Patents
预成型料用环氧树脂固化性组合物 Download PDFInfo
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- CN101379118B CN101379118B CN200780004453XA CN200780004453A CN101379118B CN 101379118 B CN101379118 B CN 101379118B CN 200780004453X A CN200780004453X A CN 200780004453XA CN 200780004453 A CN200780004453 A CN 200780004453A CN 101379118 B CN101379118 B CN 101379118B
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- carbonatoms
- epoxy resin
- hydroxyl
- arylidene
- composition
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 60
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- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- ALHBQZRUBQFZQV-UHFFFAOYSA-N tin;tetrahydrate Chemical compound O.O.O.O.[Sn] ALHBQZRUBQFZQV-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
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- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
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- 239000012953 triphenylsulfonium Substances 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
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Abstract
本发明提供含有下述(A)~(E)成分的预成型料用环氧树脂固化性组合物。(A):具有来自含酚性羟基芳香族二胺的结构的聚酰胺化合物,所述含酚性羟基芳香族二胺在与氨基相邻的位置上具有酚性羟基;(B):环氧树脂;(C):环氧树脂固化剂;(D)填充剂;(E):溶剂。
Description
技术领域
本发明涉及含有在结构中的特定部位具有酚性羟基的聚酰胺化合物的预成型料用环氧树脂固化性组合物,更详细而言,涉及通过用该聚酰胺化合物作为固化剂成分而获得线膨胀系数低的预成型料、进一步获得印刷布线板的预成型料用环氧树脂固化性组合物。
背景技术
印刷布线基板从其特性出发广泛使用环氧树脂,对于近年来伴随着小型轻量化而产生的高密度化需求,人们也正在研究用环氧树脂来解决。
特别是在预成型料等中使用的环氧树脂,通过掺入大量各种无机填料来降低线膨胀,抑制由温度引起的变形。但若掺入大量无机填料,则有时会使拉伸强度和伸长率下降,或因凝集而短路从而降低电路的可靠性等,且很难调制。
作为环氧树脂,在专利文献1中记载有由2,2-双(3,4-环氧环己基)丙烷与酸酐形成的固化物。另外,在专利文献2、专利文献3以及专利文献4中记载了掺入有具有酚性羟基的聚酰胺的环氧树脂。
但是,在专利文献2、专利文献3以及专利文献4中,对于以在与氨基相邻的位置上具有酚性羟基的羟基取代芳香族二胺为原料的本发明化合物,并未特别作为优异的化合物进行具体说明,且对于在玻璃化转变温度或线膨胀系数中显示出的优异效果也未作任何记载。
专利文献1:德国专利107798号说明书
专利文献2:日本特开2001-31784号公报的权利要求书以及第6页左栏第40行到第8页末尾的实施例
专利文献3:日本特开2001-49082号公报的权利要求书
专利文献4:日本特开2005-29720号公报的权利要求书
发明内容
因此,本发明的目的在于提供能得到玻璃化转变温度高且线膨胀系数低的预成型料的预成型料用环氧树脂固化性组合物。
本发明人等鉴于上述现状进行了潜心研究,结果发现,通过使用具有来自在与氨基相邻的位置上具有酚性羟基的羟基取代芳香族二胺的结构的聚酰胺化合物,能够获得可得到玻璃化转变温度高且线膨胀系数低的预成型料的环氧树脂固化性组合物,从而完成了本发明。
即,本发明提供含有下述(A)~(E)成分的预成型料用环氧树脂固化性组合物。
(A):具有来自含酚性羟基芳香族二胺的结构的聚酰胺化合物,所述含酚性羟基芳香族二胺在与氨基相邻的位置上具有酚性羟基;
(B):环氧树脂;
(C):环氧树脂固化剂;
(D):填充剂;
(E):溶剂。
本发明还提供上述预成型料用环氧树脂固化性组合物,其中,上述(A)成分的聚酰胺化合物的结构是:在其重复单元中具有下述通式(I)或通式(II)表示的酚性羟基。
(式中,环A表示碳原子数为6~18的亚芳基或碳原子数为13~25的亚烷基二亚芳基,这些基团可被卤原子、羟基、碳原子数为1~4的烷基取代,R表示碳原子数为2~10的亚烷基、碳原子数为6~18的亚环烷基、亚芳基或碳原子数为13~25的亚烷基二亚芳基,这些基团可被卤原子、羟基、碳原子数为1~4的烷基取代。)
(式中,环B表示碳原子数为6~18的亚芳基或碳原子数为13~25的亚烷基二亚芳基,这些基团可被卤原子、羟基、碳原子数为1~4的烷基取
代。)
本发明还提供上述预成型料用环氧树脂固化性组合物,其中,上述(A)成分的聚酰胺化合物为具有下述通式(III)或通式(IV)表示的酚性羟基的结构。
(式中,环A表示碳原子数为6~18的亚芳基或碳原子数为13~25的亚烷基二亚芳基,这些基团可被卤原子、羟基、碳原子数为1~4的烷基取代,R表示碳原子数为2~10的亚烷基、碳原子数为6~18的亚环烷基、亚芳基或碳原子数为13~25的亚烷基二亚芳基,这些基团可被卤原子、羟基、碳原子数为1~4的烷基取代,n为正数。)
(式中,环B表示碳原子数为6~18的亚芳基或碳原子数为13~25的亚烷基二亚芳基,这些基团可被卤原子、羟基、碳原子数为1~4的烷基取代,m为正数。)
而且,本发明提供由上述预成型料用环氧树脂固化性组合物制得的预成型料。
另外,本发明提供由上述预成型料制得的印刷布线板。
具体实施方式
下面,详细说明本发明。
首先,对本发明的(A)成分进行说明。
本发明的(A)成分是具有来自含酚性羟基芳香族二胺的结构的聚酰胺化合物,所述含酚性羟基芳香族二胺在与氨基相邻的位置上具有酚性羟基。本发明所谓的在与氨基相邻的位置上具有酚性羟基的含酚性羟基芳香族二胺也包括其盐。即,聚酰胺中存在来自含酚性羟基芳香族二胺或其盐的结构,所述含酚性羟基芳香族二胺在与氨基相邻的位置上具有酚性羟基。
另外,该聚酰胺化合物是以在与氨基相邻的位置上具有酚性羟基的含酚性羟基芳香族二胺(或其盐)和二羧酸类(各种芳香族二羧酸、脂肪族二羧酸或它们的酰氯、酯等)为原料而构成的聚酰胺化合物。与氨基相邻的位置上具有的酚性羟基的个数无特殊限制,例如1分子芳香族二胺中有1个~4个。
当然,该聚酰胺化合物也可将在与氨基相邻的位置上具有酚性羟基的二胺以外的二胺化合物(各种芳香族二胺、脂肪族二胺或它们的盐等)作为原料,成为进一步的构成成分,还可使用含有酚性羟基的二羧酸类(或它们的酰氯、酯等)。
作为在与氨基相邻的位置上具有酚性羟基的含酚性羟基芳香族二胺的例子,无特殊限制,可列举出间苯二胺、对苯二胺、间甲苯二胺、4,4’-二氨基二苯基醚、3,3’-二甲基-4,4’-二氨基二苯基醚、3,4’-二氨基二苯基醚、4,4’-二氨基二苯基硫醚、3,3’-二甲基-4,4’-二氨基二苯基硫醚、3,3’-二乙氧基-4,4’-二氨基二苯基硫醚、3,3’-二氨基二苯基硫醚、4,4’-二氨基二苯甲酮、3,3’-二甲基-4,4’-二氨基二苯甲酮、3,3’-二氨基二苯基甲烷、4,4’-二氨基二苯基甲烷、3,4’-二氨基二苯基甲烷、3,3’-二甲氧基-4,4’-二氨基二苯基硫醚、2,2’-双(3-氨基苯基)丙烷、2,2’-双(4-氨基苯基)丙烷、4,4’-二氨基二苯基亚砜、4,4’-二氨基二苯基砜、联苯胺、3,3’-二甲基联苯胺、3,3’-二甲氧基联苯胺、3,3’-二氨基联苯、对苯二甲基二胺、间苯二甲基二胺、邻苯二甲基二胺、2,2’-双(3-氨基苯氧基苯基)丙烷、2,2’-双(4-氨基苯氧基苯基)丙烷、1,3-双(4-氨基苯氧基苯基)苯、1,3’-双(3-氨基苯氧基苯基)丙烷、双(4-氨基-3-甲基苯基)甲烷、双(4-氨基-3,5-二甲基苯基)甲烷、双(4-氨基-3-乙基苯基)甲烷、双(4-氨基-3,5-二乙基苯基)甲烷、双(4-氨基-3-丙基苯基)甲烷、双(4-氨基-3,5-二丙基苯基)甲烷、2,2’-双(3-氨基苯基)六氟丙烷、2,2’-双(4-氨基苯基)六氟丙烷等芳香族二胺,它们在与氨基相邻的位置上结合了1个~4个羟基。但不限于这些。它们可以1种或2种以上混合使用,也可以和未结合羟基的芳香族二胺并用。作为在与氨基相邻的位置上具有酚性羟基的含酚性羟基芳香族二胺的盐的例子,可列举出上述二胺的盐。作为未结合羟基的芳香族二胺(或它们的盐)的例子,可列举出上述化合物。
另外,作为和在与氨基相邻的位置上具有酚性羟基的含酚性羟基芳香族二胺反应而构成本发明聚酰胺化合物的二羧酸类的例子,无特殊限制,例如可列举出邻苯二甲酸、间苯二甲酸、对苯二甲酸、4,4’-羟基二苯甲酸、4,4’-联苯基二羧酸、3,3’-亚甲基二苯甲酸、4,4’-亚甲基二苯甲酸、4,4’-硫代二苯甲酸、3,3’-羰基二苯甲酸、4,4’-羰基二苯甲酸、4,4’-磺酰二苯甲酸、1,5-萘二羧酸、1,4-萘二羧酸、2,6-萘二羧酸、1,2-萘二羧酸、5-羟基间苯二甲酸、4-羟基间苯二甲酸、2-羟基间苯二甲酸、3-羟基间苯二甲酸、2-羟基对苯二甲酸、2,2’-双(3-羧基苯基)六氟丙烷、2,2’-双(4-羧基苯基)六氟丙烷等。它们可以1种或2种以上混合使用。作为二羧酸类的酰氯或酯的例子,可列举出上述二羧酸类的酰氯或酯。
本发明的(A)成分聚酰胺化合物的优选结构的特征为,在其重复单元中具有下述通式(I)或(II)表示的结构,在该结构中在与氨基相邻的位置上具有酚性羟基。
(式中,环A表示碳原子数为6~18的亚芳基或碳原子数为13~25的亚烷基二亚芳基,这些基团可被卤原子、羟基、碳原子数为1~4的烷基取代,R表示碳原子数为2~10的亚烷基、碳原子数为6~18的亚环烷基、亚芳基或碳原子数为13~25的亚烷基二亚芳基,这些基团可被卤原子、羟基、碳原子数为1~4的烷基取代。)
(式中,环B表示碳原子数为6~18的亚芳基或碳原子数为13~25的亚烷基二亚芳基,这些基团可被卤原子、羟基、碳原子数为1~4的烷基取代。)
作为上述通式(I)中的环A或上述通式(II)中的环B所表示的碳原子数为6~18的亚芳基,可列举出1,2-亚苯基、1,3-亚苯基、1,4-亚
苯基、1,5-亚萘基、2,5-亚萘基、蒽-二基、4,4’-亚联苯基、4,4’-对亚联三苯基、4,4’-间亚联三苯基、2-氟-1,4-亚苯基、2,5-二甲基-1,4-亚苯基等。
作为上述通式(I)中的环A或上述通式(II)中的环B所表示的碳原子数为13~25的亚烷基二亚芳基,可列举出亚甲基二亚苯基、亚乙基二亚苯基、亚丙基二亚苯基、亚异丙基二亚苯基、六氟亚异丙基二亚苯基、亚丙基-3,3’,5,5’-四氟二亚苯基、芴-9-亚基二亚苯基等。
作为上述通式(I)中的R所表示的碳原子数为2~10的亚烷基,可列举出亚乙基、亚丙基、三亚甲基、四亚甲基、2,2-二甲基三亚甲基、六亚甲基、八亚甲基、十亚甲基等。
作为上述通式(I)中的R所表示的碳原子数为6~18的亚环烷基,可列举出环己烷、环庚烷、环辛烷、双环己烷、二环己烷等的二价基团。
作为上述通式(I)中的R所表示的亚芳基,可列举出与上述环A中的亚芳基相同的基团。
作为上述通式(I)中的R所表示的亚烷基二芳基,可列举出与上述环A中的亚烷基二芳基相同的基团。
另外,作为本发明(A)成分的聚酰胺化合物的优选结构,可列举出具有在重复单元中仅含有上述通式(I)或上述通式(II)的结构的下述通式(III)或下述通式(IV)的结构。
(式中,环A表示碳原子数为6~18的亚芳基或碳原子数为13~25的亚烷基二亚芳基,这些基团可被卤原子、羟基、碳原子数为1~4的烷基取代,R表示碳原子数为2~10的亚烷基、碳原子数为6~18的亚环烷基、亚芳基或碳原子数为13~25的亚烷基二亚芳基,这些基团可被卤原子、羟基、碳原子数为1~4的烷基取代。n为正数。)
(式中,环B表示碳原子数为6~18的亚芳基或碳原子数为13~25的亚烷基二亚芳基,这些基团可被卤原子、羟基、碳原子数为1~4的烷基取代。m为正数。)
作为上述通式(III)中的环A所表示的亚芳基,可列举出与上述通式(I)中的亚芳基相同的基团。
作为上述通式(III)中的环A所表示的亚烷基二亚芳基,可列举出与上述通式(I)中的亚烷基二亚芳基相同的基团。
作为上述通式(III)中的R所表示的碳原子数为2~10的亚烷基,可列举出与上述通式(I)中的亚烷基相同的基团。
作为上述通式(III)中的R所表示的碳原子数为6~18的亚环烷基,可列举出与上述通式(I)中的亚环烷基相同的基团。
作为上述通式(III)中的R所表示的亚芳基,可列举出与上述通式(I)中的亚芳基相同的基团。
作为上述通式(III)中的R所表示的亚烷基二亚芳基,可列举出与上述通式(I)中的亚烷基二亚芳基相同的基团。
作为上述通式(IV)中的环B所表示的亚芳基,可列举出与上述通式(II)中的亚芳基相同的基团。
作为上述通式(IV)中的环B所表示的亚烷基二亚芳基,可列举出与上述通式(II)中的亚烷基二亚芳基相同的基团。
作为本发明(A)成分的聚酰胺化合物的优选的更具体的结构,例如可列举出以下No.1~20的结构。但本发明不受以下结构的任何限制。
从固化物物性的观点出发,本发明预成型料用环氧树脂固化性组合物中的上述(A)成分的聚酰胺化合物的含量优选为1~98质量%,特别优选为1~90质量%。
下面,对本发明的(B)成分即环氧树脂进行说明。
作为上述(B)成分的环氧树脂,无特殊限制,可使用公知的芳香族环氧化合物、脂环族环氧化合物、脂肪族环氧化合物等。作为芳香族环氧化合物,例如可列举出对苯二酚、间苯二酚、双酚A、双酚F、4,4’-二羟基联苯、酚醛清漆、四溴双酚A、2,2-双(4-羟基苯基)-1,1,1,3,3,3-六氟丙烷、1,6-二羟基萘等多元酚的缩水甘油醚化合物。作为脂环族环氧化合物,可列举出至少具有1个以上脂环族环的多元醇的多缩水甘油醚或将含有环己烯或环戊烯环的化合物用氧化剂进行环氧化后得到的含有氧化环己烯或氧化环戊烯的化合物。例如氢化双酚A二缩水甘油醚、3,4-环氧环己基甲基-3,4-环氧环己基羧酸酯、3,4-环氧-1-甲基环己基-3,4-环氧-1-甲基己烷羧酸酯、6-甲基-3,4-环氧环己基甲基-6-甲基-3,4-环氧环己烷羧酸酯、3,4-环氧-3-甲基环己基甲基-3,4-环氧-3-甲基环己烷羧酸酯、3,4-环氧-5-甲基环己基甲基-3,4-环氧-5-甲基环己烷羧酸酯、双(3,4-环氧环己基甲基)己二酸酯、亚甲基双(3,4-环氧环己烷)、2,2-双(3,4-环氧环己基)丙烷、双环戊二烯二环氧化物、亚乙基双(3,4-环氧环己烷羧酸酯)、环氧六氢化邻苯二甲酸二辛酯、环氧六氢化邻苯二甲酸二-2-乙基己酯等。作为脂肪族环氧化合物,可列举出脂肪族多元醇或其烯化氧加成物的多缩水甘油醚、脂肪族长链多元酸的多缩水甘油酯、丙烯酸缩水甘油酯或甲基丙烯酸缩水甘油酯通过乙烯聚合合成的均聚物、丙烯酸缩水甘油酯或甲基丙烯酸缩水甘油酯与其它乙烯基单体通过乙烯聚合合成的共聚物等。作为代表性化合物,可列举出1,4-丁二醇二缩水甘油醚、1,6-己二醇二缩水甘油醚、甘油的三缩水甘油醚、三羟甲基丙烷的三缩水甘油醚、山梨糖醇的四缩水甘油醚、二季戊四醇的六缩水甘油醚、聚乙二醇的二缩水甘油醚、聚丙二醇的二缩水甘油醚等多元醇的缩水甘油醚,丙二醇、三羟甲基丙烷、甘油等脂肪族多元醇与1种或2种以上的烯化氧加成得到的聚醚多元醇的多缩水甘油醚,脂肪族长链二元酸的二缩水甘油酯。此外,还可列举出高级脂肪族醇的单缩水甘油醚或苯酚、甲酚、丁基苯酚、以及它们与烯化氧加成得到的聚醚醇的单缩水甘油醚、高级脂肪酸的缩水甘油
酯、环氧化大豆油、环氧硬脂酸辛酯、环氧硬脂酸丁酯、环氧化聚丁二烯等。
从固化物物性的观点出发,本发明预成型料用环氧树脂固化性组合物中的上述(B)成分的环氧树脂的含量优选为1~90质量%,特别优选为1~50质量%。
下面,对本发明的(C)成分即环氧树脂固化剂进行说明。
作为上述(C)成分的环氧树脂固化剂,可列举出潜在性固化剂、多胺化合物、多酚化合物以及阳离子类光引发剂等,也包括所谓的固化促进剂。
作为潜在性固化剂,可列举出双氰胺、酰肼、咪唑化合物、胺加成物、锍盐、鎓盐、酮亚胺、酸酐、叔胺等。这些潜在性固化剂提供单组分型的固化性组合物,操作容易,因而优选。
作为酸酐,例如可列举出邻苯二甲酸酐、偏苯三酸酐、均苯四酸酐、四氢邻苯二甲酸酐、六氢邻苯二甲酸酐、马来酸酐、琥珀酸酐、2,2-双(3,4-二羧基苯基)-1,1,1,3,3,3-六氟丙烷二酐等。
作为多胺化合物,例如可列举出乙二胺、二乙三胺、三乙四胺等脂肪族多胺,孟烷二胺、异佛尔酮二胺、双(4-氨基-3-甲基环己基)甲烷、双(氨基甲基)环己烷、3,9-双(3-氨基丙基)-2,4,8,10-四氧杂螺[5,5]十一烷等脂环族多胺,间苯二甲胺等具有芳香环的脂肪族胺,间苯二胺、2,2-双(4-氨基苯基)丙烷、二氨基二苯基甲烷、二氨基二苯基砜、α,α-双(4-氨基苯基)对二异丙基苯、2,2-双(4-氨基苯基)-1,1,1,3,3,3-六氟丙烷等芳香族多胺。
作为多酚化合物,例如可列举出酚醛清漆树脂、邻甲酚酚醛清漆、叔丁基苯酚酚醛清漆、二环戊二烯甲酚、萜烯联苯酚、萜烯联儿茶酚、1,1,3-三(3-叔丁基-4-羟基-6-甲基苯基)丁烷、亚丁基双(3-叔丁基-4-羟基-6-甲基苯基)、2,2-双(4-羟基苯基)-1,1,1,3,3,3-六氟丙烷等。酚醛清漆树脂所得到的环氧树脂的电特性、机械强度适合层压板,因而优选。
作为咪唑化合物,例如可列举出2-甲基咪唑、2-苯基咪唑、2-十一烷基咪唑、2-十七烷基咪唑、2-苯基-4-甲基咪唑、1-苄基-2-苯基咪唑、1-苄基-2-甲基咪唑、1-氰基乙基-2-甲基咪唑、1-氰基乙基-2-苯基咪唑、1-氰基乙基-2-十一烷基咪唑、2,4-二氨基-6(2’-甲基咪唑(1’))乙基-s-三嗪、2,4-二氨基-6(2’-十一烷基咪唑(1’))乙基-s-三嗪、2,4-二氨基-6(2’-乙
基-4-甲基咪唑(1’))乙基-s-三嗪、2,4-二氨基-6(2’-甲基咪唑(1’))乙基-s-三嗪·三聚异氰酸加成物、2-甲基咪唑三聚异氰酸的2∶3加成物、2-苯基咪唑三聚异氰酸加成物、2-苯基-3,5-二羟基甲基咪唑、2-苯基-4-羟基甲基-5-甲基咪唑、1-氰基乙基-2-苯基-3,5-二氰基乙氧基甲基咪唑等各种咪唑类,以及这些咪唑类和邻苯二甲酸、间苯二甲酸、对苯二甲酸、偏苯三酸、均苯四酸、萘二羧酸、马来酸、草酸等多元酸的盐类。
本发明中可使用的阳离子类光引发剂是在能量线照射下能放出可引发阳离子聚合的物质的化合物,特别优选通过照射而放出路易斯酸的鎓盐即复盐或其衍生物。作为所述化合物的代表性物质,可列举出下述通式所表示的阳离子与阴离子的盐。
[A]m+[B]m-
这里,阳离子[A]m+优选为鎓,其结构例如可由以下通式来表示。
[(R1)Q]m+
此外,这里R1是碳原子数为1~60的可含有几个碳原子以外的原子的有机基团。a是1~5的整数。a个R1可分别相同也可以不同。另外,优选a个R1中的至少一个为具有芳香环的上述有机基团。Q是选自S、N、Se、Te、P、As、Sb、Bi、O、I、Br、Cl、F、N=N中的原子或原子团。另外,当阳离子[A]m+中的Q的原子价为q时,必须满足m=a-q的关系(N=N的原子价作为0处理)。
阴离子[B]m-优选为卤化物络合物,其结构例如可由以下通式来表示。
[LXb]m-
这里,L是作为卤化物络合物的中心原子的金属或准金属,是B、P、As、Sb、Fe、Sn、Bi、Al、Ca、In、Ti、Zn、Sc、V、Cr、Mn、Co等。X为卤原子。b为3~7的整数。
当阴离子[B]m-中L的原子价为p时,必须满足m=b-p的关系。
作为上述通式表示的阴离子[LXb]m-的具体例子,可列举出四氟化硼(BF4)-、六氟化磷(PF6)-、六氟化锑(SbF6)-、六氟化砷(AsF6)-、六氯
化锑(SbCl6)-等。
另外,阴离子Bm-还可优选使用下式表示的结构。L、X、b与上述同样。作为其他可使用的阴离子,可列举出高氯酸离子(ClO4)-、三氟甲基亚硫酸离子(CF3SO3)-、氟磺酸离子(FSO3)-、甲苯磺酸阴离子、三硝基苯磺酸阴离子等。
[LXb-1(OH)]m-
本发明中,使用上述鎓盐中下述1)~3)的芳香族鎓盐特别有效。它们可以单独使用1种,或2种以上混合使用。优选为:
1)苯基重氮鎓六氟磷酸盐、4-甲氧基苯基重氮鎓六氟锑酸盐、4-甲基苯基重氮鎓六氟磷酸盐等芳基重氮鎓盐;
2)二苯基碘鎓六氟锑酸盐、二(4-甲基苯基)碘鎓六氟磷酸盐、二(4-叔丁基苯基)碘鎓六氟磷酸盐等二芳基碘鎓盐;
3)三苯基锍鎓六氟锑酸盐、三(4-甲氧基苯基)锍鎓六氟磷酸盐、二苯基-4-硫代苯氧基苯基锍鎓六氟锑酸盐、二苯基-4-硫代苯氧基苯基锍鎓六氟磷酸盐、4,4’-双(二苯基锍基)苯基硫-双六氟锑酸盐、4,4’-双(二苯基锍基)苯基硫-双六氟磷酸盐、4,4’-双[二(β-羟基乙氧基)苯基锍基]苯基硫-双六氟锑酸盐、4,4’-双[二(β-羟基乙氧基)苯基锍基]苯基硫-双六氟磷酸盐、4-[4’-(苯甲酰基)苯基硫代]苯基-二(4-氟苯基)锍鎓六氟锑酸盐、4-[4’-(苯甲酰基)苯基硫代]苯基-二(4-氟苯基)锍鎓六氟磷酸盐等三芳基锍鎓盐等。
作为其他优选的物质,还可列举出(η5-2,4-环戊二烯-1-基)[(1,2,3,4,5,6,-η)-(1-甲基乙基)苯]-铁-六氟磷酸盐等铁-芳烃络合物或三(乙酰丙酮)铝、三(乙基丙酮乙酸)铝、三(水杨醛)铝等铝络合物与三苯基硅烷醇等硅烷醇类的混合物等。
其中,从实用性和光感度的观点出发,优选使用芳香族碘鎓盐、芳香族锍鎓盐、铁-芳烃络合物。
上述光引发剂可与苯甲酸类或叔胺类等公知的光聚合促进剂中的1种或2种以上组合使用。
作为采用光引发剂时的聚合中所使用的光源,可采用高压汞灯、金属卤化物灯、氙灯等公知光源,通过照射紫外线、电子射线、X射线、放射
线、高频射线等活性能量线,从上述光引发剂放出路易斯酸,从而使上述环氧化合物固化。作为上述光源,具有400nm以下波长的光源有效。
关于使用上述(C)成分的固化剂中的何种固化剂,可适当选择。特别优选潜在性固化剂,尤其优选咪唑化合物。
从固化物物性的观点出发,本发明预成型料用环氧树脂固化性组合物中的上述(C)成分的环氧树脂固化剂的含量优选为0.01~20质量%,特别优选0.1~5质量%。上述固化剂也可以2种以上混合使用。
下面,对本发明(D)成分即填充剂进行说明。
作为上述(D)成分的填充剂(填料)无特殊限制,可使用以往公知的填充剂,但优选使用玻璃纤维、硼酸铝晶须、氮化硼晶须、钛酸钾晶须、氧化钛晶须等纤维状填充剂,或二氧化硅、熔融二氧化硅、氧化铝等球状填充剂,从固化物物性(低线膨胀系数)的观点出发,特别优选球状二氧化硅或球状熔融二氧化硅。当然,不限于纤维状、球状的形态,也可使用二氧化硅(熔融二氧化硅、结晶性二氧化硅)、氧化铝、硼酸铝、氮化铝、氮化硅、氮化硼、钛酸钾、氧化钛等,此外,作为填充剂,还可列举出滑石、云母、碳酸钙、玻璃片、玻璃珠、玻璃球、硅酸钙、氢氧化铝、硫酸钡、氧化镁、铁氧体、各种金属微粒、石墨、碳,碳纤维、硼纤维、碳化硅纤维、氧化铝纤维、硅铝纤维等无机类纤维,芳香族聚酰胺纤维、聚酯纤维、纤维素纤维、碳纤维等有机类纤维等。
纤维状填充剂优选根据用途适当选择长轴方向的长度和纵横比,球状填充剂优选是正圆球状且粒径小,特别优选平均粒径在0.1~20μm的范围内。
从固化物物性的观点出发,本发明预成型料用环氧树脂固化性组合物中的上述(D)成分的填充剂的含量优选为0.1~97质量%,特别优选为1~95质量%。
下面,对本发明的(E)成分即溶剂进行说明。
作为上述(E)成分的溶剂,例如可列举出γ-丁内酯类、N-甲基吡咯烷酮(NMP)、N,N-二甲基甲酰胺(DMF)、N,N-二甲基乙酰胺、N,N-二甲基咪唑啉酮等酰胺类溶剂,环丁砜等砜类,二乙二醇二甲基醚、二乙二醇二乙基醚、丙二醇、丙二醇单甲基醚、丙二醇单甲基醚单乙酸酯、丙二醇单丁基醚等醚类溶剂,甲乙酮、甲基异丁基酮、环戊酮、环己酮等酮
类溶剂,甲苯、二甲苯等芳香族类溶剂。其中,从溶解性和易干燥性的观点出发,优选二乙二醇二甲基醚、二乙二醇二乙基醚、丙二醇、丙二醇单甲基醚、丙二醇单甲基醚单乙酸酯、丙二醇单丁基醚等醚类溶剂。
本发明预成型料用环氧树脂固化性组合物中的上述(E)成分的溶剂的含量优选为0.01~80质量%,特别优选10~70质量%。
本发明预成型料用环氧树脂组合物除上述(A)~(E)成分外,还可根据需要含有任意成分。
作为任意成分,例如可列举出天然蜡类、合成蜡类以及长链脂肪族酸的金属盐类等增塑剂,酰胺类、酯类、石蜡类等脱膜剂,丁腈橡胶、丁二烯橡胶等应力缓和剂,三氧化锑、五氧化锑、氧化锡、氢氧化锡、氧化钼、硼酸锌、偏硼酸钡、红磷、氢氧化铝、氢氧化镁、铝酸钙等无机阻燃剂,四溴双酚A、四溴邻苯二甲酸酐、六溴苯、溴化酚醛清漆树脂等溴类阻燃剂,磷酸酯类阻燃剂,磷酸酰胺类阻燃剂,硅烷类偶联剂、钛酸酯类偶联剂、铝类偶联剂等偶联剂,染料和颜料等着色剂,氧化稳定剂,光稳定剂,耐湿性提高剂,触变性赋予剂,稀释剂,消泡剂,其他各种树脂,粘附赋予剂,防静电剂,润滑剂,紫外线吸收剂等。
下面,对用本发明的预成型料用环氧树脂固化性组合物制作预成型料时使用的基材进行说明。
预成型料的基材可以采用以往使用的基材,例如可列举出由玻璃纤维、全芳香族聚酯纤维、酚醛树脂纤维、芳香族聚酰胺纤维、聚酰亚胺纤维、碳纤维、聚吲哚(PBZ)纤维等形成的织物或无纺布,从所得预成型料的线膨胀系数低的观点出发,优选由芳香族聚酰胺纤维形成的织物、无纺布,由聚吲哚纤维形成的织物、无纺布。
通过将本发明预成型料用环氧树脂固化性组合物在基材上涂布、浸渗后加热这一普通方法即可制造预成型料。而且,通过使多张上述预成型料重叠,在其层叠结构的单面或双面上重叠铜箔,然后将其在普通条件下加热、加压,可得到覆铜层压板。此时,若不使用铜箔,也可得到层压板。另外,在该覆铜层压板(内层板)上形成电路,然后对铜箔进行蚀刻处理后,在内层板的至少一个面上重叠预成型料和铜箔,将其通过例如在170℃、40kg/cm2的压力下加热、加压90分钟这一普通方法即可制造多层板。此外,通过在该覆铜层压板或该多层板上形成通孔,进行通孔电镀,然后
形成规定的电路这一普通方法即可制造印刷布线板。
实施例
通过实施例详细说明本发明。但本发明不受以下实施例的任何限制。
[合成例1]具有上述No.1的结构的上述(A)成分的聚酰胺化合物的合成
向在N-甲基吡咯烷酮(NMP)40g和吡啶15.33g的混合物中溶解2,2-双(3-氨基-4-羟基苯基)六氟丙烷16.48g(0.045mol)而形成的溶液中,在-15~0℃下滴加在40gNMP中溶解间苯二酰氯10.05g(0.0495mol)而形成的溶液。在保持-15~0℃的条件下反应2小时,再在室温下反应2小时。用约2升的离子交换水进行再沉淀后,过滤并在150℃下减压干燥3小时,得到白色粉末17.9g(收率80.1%)(下述的实施聚合物1)。
对得到的白色粉末的化合物,通过红外吸收光谱证实了酰胺键的形成,通过凝胶渗透色谱证实了该化合物是重均分子量为20000的聚合物。另外,通过分析可知,其粘度为50cps(25℃、30重量%NMP溶液),且OH当量为250g/eq。
实施聚合物1
粘度:50cps
(25℃、30wt.%NMP溶液)
重均分子量:20000
OH当量:250g/eq
[合成例2~20]
与合成例1同样操作,合成了下述实施聚合物2~20。得到的实施聚合物的重均分子量、粘度、OH当量如下所示。
实施聚合物2
粘度:50cps
(25℃、30wt.%NMP溶液)
重均分子量:20000
OH当量:484g/eq
实施聚合物3
粘度:50cps
(25℃、30wt.%NMP溶液)
重均分子量:20000
OH当量:363g/eq
实施聚合物4
粘度:150cps
(25℃、30wt.%NMP溶液)
重均分子量:20000
OH当量:288g/eq
实施聚合物5
粘度:200cps
(25℃、30wt.%NMP溶液)
重均分子量:20000
OH当量:288g/eq
实施聚合物6
粘度:200cps
(25℃、30wt.%NMP溶液)
重均分子量:20000
OH当量:320g/eq
实施聚合物7
粘度:150cps
(25℃、30wt.%NMP溶液)
重均分子量:24000
OH当量:722g/eq
实施聚合物8
粘度:150cps
(25℃、30wt.%NMP溶液)
重均分子量:15000
OH当量:708g/eq
实施聚合物9
粘度:150cps
(25℃、30wt.%NMP溶液)
重均分子量:15000
OH当量:716g/eq
实施聚合物10
粘度:150cps
(25℃、30wt.%NMP溶液)
重均分子量:15000
OH当量:906g/eq
实施聚合物11
粘度:200cps
(25℃、30wt.%NMP溶液)
重均分子量:15000
OH当量:798g/eq
实施聚合物12
粘度:200cps
(25℃、30wt.%NMP溶液)
重均分子量:15000
OH当量:680g/eq
实施聚合物13
粘度:200cps
(25℃、30wt.%NMP溶液)
重均分子量:15000
OH当量:680g/eq
实施聚合物14
粘度:250cps
(25℃、30wt.%NMP溶液)
重均分子量:15000
OH当量:546g/eq
实施聚合物15
粘度:100cps
(25℃、30wt.%NMP溶液)
重均分子量:20000
OH当量:257g/eq
实施聚合物16
粘度:100cps
(25℃、30wt.%NMP溶液)
重均分子量:15000
OH当量:860g/eq
实施聚合物17
粘度:100cps
(25℃、30wt.%NMP溶液)
重均分子量:15000
OH当量:708g/eq
实施聚合物18
粘度:100cps
(25℃、30wt.%NMP溶液)
重均分子量:20000
OH当量:377g/eq
实施聚合物19
粘度:150cps
(25℃、30wt.%NMP溶液)
重均分子量:20000
OH当量:736g/eq
实施聚合物20
粘度:200cps
(25℃、30wt.%NMP溶液)
重均分子量:15000
OH当量:604g/eq
[实施例1~24以及比较例1~6]
用上述合成例中得到的实施聚合物或后述的比较聚合物,按表1~表5所述的配方分别制备预成型料用环氧树脂固化性组合物。用这些环氧树脂固化性组合物和表1~表5所述的基材制作预成型料,将4张上述预成型料层叠并在其表面粘贴5μm的铜箔,在真空下、180℃、50kg/cm2下加压90分钟,测定玻璃化转变温度和线膨胀系数。其结果如表1~表5所示。
玻璃化转变温度使用切成宽5mm、长40mm的长方形样品,通过动态粘弹性法测定。
线膨胀系数使用切成宽3mm、长10mm的长方形样品,通过TMA测定。
[表1]
实施例1 | 实施例2 | 实施例3 | 实施例4 | 实施例5 | 实施例6 | |
实施聚合物1 | 10g | 10g | 10g | 10g | 10g | |
实施聚合物2 | 10g | |||||
环氧树脂1*1 | 5.7g | 10g | 10g | 10g | 7.5g | 3.0g |
球状二氧化硅*2 | 2.2g (6vol.%) | 2.8g (6vol.%) | 2.8g (6vol.%) | 13g (24vol.%) | 12.1g (20vol.%) | 8.6g (24vol.%) |
TiO2晶须*3 | 0 | 0 | 0 | 0 | 7g (10vol.%) | 0 |
咪唑类固化剂*4 | 0.08g | 0.14g | 0.14g | 0.14g | 0.11g | 0.07g |
PGM*5 | 20g | 20g | 20g | 20g | 20g | 20g |
基材 | 芳香族聚酰 胺无纺布 | 玻璃布 | 芳香族聚 酰胺布 | PBZ无纺 布 | PBZ布 | PBZ布 |
玻璃化转变温度 | 270℃ | 270℃ | 270℃ | 270℃ | 270℃ | 212℃ |
线膨胀系数 | 7ppm | 18ppm | 6ppm | 5ppm | 3ppm | 4ppm |
[表2]
实施例7 | 实施例8 | 实施例9 | 实施例10 | 实施例11 | 实施例12 | |
实施聚合物3 | 10g | |||||
实施聚合物4 | 10g | |||||
实施聚合物5 | 10g | |||||
实施聚合物6 | 10g | |||||
实施聚合物7 | 10g | |||||
实施聚合物8 | 10g | |||||
环氧树脂1*1 | 4.0g | 5.0g | 5.0g | 4.5g | 2.0g | 2.0g |
球状二氧化硅*2 | 9.3g (24vol.%) | 9.9g (24vol.%) | 9.9g (24vol.%) | 9.6g (24vol.%) | 7.9g (24vol.%) | 6.7g (24vol.%) |
咪唑类固化剂*4 | 0.08g | 0.08g | 0.08g | 0.08g | 0.05g | 0.05g |
PGM*5 | 20g | 20g | 20g | 20g | 20g | 20g |
基材 | PBZ布 | PBZ布 | PBZ布 | PBZ布 | PBZ布 | PBZ布 |
玻璃化转变温度 | 280℃ | 230℃ | 225℃ | 205℃ | 215℃ | 230℃ |
线膨胀系数 | 5ppm | 5ppm | 5ppm | 4ppm | 4ppm | 4ppm |
[表3]
实施例13 | 实施例14 | 实施例15 | 实施例16 | 实施例17 | 实施例18 | |
实施聚合物9 | 10g | |||||
实施聚合物10 | 10g | |||||
实施聚合物11 | 10g | |||||
实施聚合物12 | 10g | |||||
实施聚合物13 | 10g | |||||
实施聚合物14 | 10g | |||||
环氧树脂1*1 | 4.0g | 1.6g | 1.8g | 2.1g | 2.1g | 2.6g |
球状二氧化硅*2 | 9.3g (24vol.%) | 7.7g (24vol.%) | 7.8g (24vol.%) | 8.0g (24vol.%) | 8.0g (24vol.%) | 8.3g (24vol.%) |
咪唑类固化剂*4 | 0.08g | 0.05g | 0.05g | 0.05g | 0.05g | 0.06g |
PGM*5 | 20g | 20g | 20g | 20g | 20g | 20g |
基材 | PBZ布 | PBZ布 | PBZ布 | PBZ布 | PBZ布 | PBZ布 |
玻璃化转变温度 | 170℃ | 200℃ | 170℃ | 175℃ | 185℃ | 200℃ |
线膨胀系数 | 6ppm | 3ppm | 4ppm | 3ppm | 3ppm | 3ppm |
[表4]
实施例19 | 实施例20 | 实施例21 | 实施例22 | 实施例23 | 实施例24 | |
实施聚合物15 | 10g | |||||
实施聚合物16 | 10g | |||||
实施聚合物17 | 10g | |||||
实施聚合物18 | 10g | |||||
实施聚合物19 | 10g | |||||
实施聚合物20 | 10g | |||||
环氧树脂1*1 | 5.6g | 1.7g | 2.0g | 3.8g | 2.0g | 2.4g |
球状二氧化硅*2 | 10.3g (24vol.%) | 7.7g (24vol.%) | 7.9g (24vol.%) | 9.1g (24vol.%) | 6.7g (24vol.%) | 6.7g (24vol.%) |
咪唑类固化剂*4 | 0.08g | 0.05g | 0.05g | 0.08g | 0.05g | 0.06g |
PGM*5 | 20g | 20g | 20g | 20g | 20g | 20g |
基材 | PBZ布 | PBZ布 | PBZ布 | PBZ布 | PBZ布 | PBZ布 |
玻璃化转变温度 | 235℃ | 190℃ | 185℃ | 240℃ | 230℃ | 175℃ |
线膨胀系数 | 3ppm | 3ppm | 3ppm | 3ppm | 3ppm | 3ppm |
[表5]
比较例1 | 比较例2 | 比较例3 | 比较例4 | 比较例5 | 比较例6 | |
比较聚合物1*6 | 10g | 10g | ||||
比较聚合物2*7 | 10g | 10g | ||||
环氧树脂1*1 | 4.8g | 4.8g | 4.8g | 4.8g | 13.6g | 13.6g |
酚醛树脂1*8 | 10.5g | 10.5g | ||||
球状二氧化硅*2 | 2.0g (6vol.%) | 2.0g (6vol.%) | 2.0g (6vol.%) | 2.0g (6vol.%) | 3.4g (6vol.%) | 3.4g (6vol.%) |
咪唑类固化剂*4 | 0.143g | 0.143g | 0.18g | 0.18g | 0.14g | 0.14g |
PGM*5 | 10g | 10g | 10g | 10g | 10g | 10g |
基材 | 玻璃布 | PBZ布 | 玻璃布 | PBZ布 | 玻璃布 | PBZ布 |
玻璃化转变温度 | 165℃ | 165℃ | 170℃ | 170℃ | 150℃ | 150℃ |
线膨胀系数 | 35ppm | 20ppm | 40ppm | 22ppm | 45ppm | 30ppm |
表1~表5中,球状二氧化硅的vol%表示配合物中的球状二氧化硅的体积比。另外,表1~表5中的*1~*8分别如下所述。
*1:环氧树脂1
*2:球状二氧化硅平均粒径0.1~20μm
*3:二氧化钛晶须
*4:咪唑类固化剂 2-苯基-4,5-二羟基甲基咪唑
*5:PGM 丙二醇单甲基醚
*6:比较聚合物1
粘度:150cps
(25℃、30wt%NMP溶液)
重均分子量:1450
OH当量:285g/eq
*7:比较聚合物2
粘度:150cps
(25℃、30wt%NMP溶液)
重均分子量:1450
OH当量:285g/eq
*8:酚醛树脂1
OH当量:105g/eq
根据本发明,能够提供玻璃化转变温度高且线膨胀系数低的预成型料。
Claims (4)
1.预成型料用环氧树脂固化性组合物,其含有下述(A)~(E)成分,
(A):具有来自含酚性羟基芳香族二胺的结构的聚酰胺化合物,所述含酚性羟基芳香族二胺在与氨基相邻的位置上具有酚性羟基;
(B):环氧树脂;
(C):环氧树脂固化剂;
(D):填充剂;
(E):溶剂;
所述(A)成分的聚酰胺化合物的结构是:在其重复单元中具有下述通式(I)或通式(II)表示的酚性羟基,
式中,环A表示亚苯基,这些基团可被卤原子、碳原子数为1~4的烷基取代,R表示碳原子数为2~10的亚烷基、碳原子数为6~18的亚环烷基、亚芳基或碳原子数为13~25的亚烷基二亚芳基,这些基团可被卤原子、羟基、碳原子数为1~4的烷基取代;
式中,环B表示亚苯基,这些基团可被卤原子、碳原子数为1~4的烷基取代;
所述(B)成分的环氧树脂的含量为1~1000/42.94质量%,且所述(A)成分的聚酰胺化合物的含量为1000/42.94~90质量%。
3.预成型料,其是由权利要求1或2所述的预成型料用环氧树脂固化性组合物制得的。
4.印刷布线板,其是由权利要求3所述的预成型料制得的。
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JP2006071417A JP5004483B2 (ja) | 2006-03-15 | 2006-03-15 | プリプレグ用エポキシ樹脂硬化性組成物 |
PCT/JP2007/052173 WO2007108242A1 (ja) | 2006-03-15 | 2007-02-08 | プリプレグ用エポキシ樹脂硬化性組成物 |
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US20100255740A1 (en) | 2009-04-01 | 2010-10-07 | Taiwan Union Technology Corporation | Epoxy resin blend |
US9180261B2 (en) * | 2010-01-12 | 2015-11-10 | Dance Biopharm Inc. | Preservative free insulin formulations and systems and methods for aerosolizing |
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CN102286190B (zh) * | 2011-06-23 | 2013-04-17 | 浙江华正新材料股份有限公司 | 一种无卤树脂组合物及用该组合物制成的覆铜板 |
CN102875968B (zh) * | 2011-07-11 | 2016-05-11 | 滁州格美特科技有限公司 | 一种阻燃增强型环氧塑料板材及其制备方法 |
TWI480319B (zh) * | 2011-11-29 | 2015-04-11 | Mitsubishi Rayon Co | 預浸體、纖維強化複合材料及其製造方法、環氧樹脂組成物 |
CN102675595B (zh) * | 2012-04-18 | 2014-07-02 | 上海维凯化学品有限公司 | 羟基酰胺型环氧树脂热潜在固化剂及其合成方法 |
JP5988220B2 (ja) | 2012-09-28 | 2016-09-07 | パナソニックIpマネジメント株式会社 | プリプレグ、金属張積層板、プリント配線板、多層プリント配線板 |
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EP1995271A4 (en) | 2012-03-28 |
CN101379118A (zh) | 2009-03-04 |
JP5004483B2 (ja) | 2012-08-22 |
WO2007108242A1 (ja) | 2007-09-27 |
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