CN118055978A - 固化性树脂组合物、固化物及粘接剂 - Google Patents
固化性树脂组合物、固化物及粘接剂 Download PDFInfo
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- CN118055978A CN118055978A CN202280066927.8A CN202280066927A CN118055978A CN 118055978 A CN118055978 A CN 118055978A CN 202280066927 A CN202280066927 A CN 202280066927A CN 118055978 A CN118055978 A CN 118055978A
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
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Abstract
本发明的目的在于提供可得到导电性、固化性优异的固化物的固化性树脂组合物。本发明为含有(A)氰酸酯树脂、(B)环氧树脂、(C)含有使胺化合物与环氧化合物反应而得到的具有活性氢的胺系潜在性固化剂的潜在性固化剂及(D)导电性填料的固化性树脂组合物。作为(C)成分的潜在性固化剂优选进一步含有酚醛树脂,作为(D)成分的导电性填料优选为选自银粒子及铜粒子中的1种以上。
Description
技术领域
本发明涉及含有氰酸酯树脂、环氧树脂、潜在性固化剂及导电性填料的固化性树脂组合物。
背景技术
以往,作为电子部件等的导电接合剂,使用了焊料,但大多情况下使用了Sn-Pb合金。但是,由于含有铅,因此对人体和环境造成不良影响令人担忧,此外,还存在耐热性低的课题。于是,作为焊料的替代,逐渐变成适用在高分子材料中配合导电性填料而得到的导电性粘接剂。导电性粘接剂存在对环境的负荷小、能够进行低温安装、进而即使是高温下也能够维持粘接强度等优点。
提出了许多将导电性填料配合到聚合物中的技术。例如,在专利文献1中,提出了在含有氰酸酯树脂、环氧树脂及潜在性固化剂而得到的粘接剂组合物中配合金属粒子等导电粒子。作为实施例中优选的例子,记载了以咪唑改性体作为核的芯壳型固化剂,但并不能够满足导电性、固化性。
现有技术文献
专利文献
专利文献1:日本特开平9-279121号公报
发明内容
发明所要解决的课题
本发明所要解决的课题是提供可得到导电性、固化性优异的固化物的固化性树脂组合物。
用于解决课题的手段
本发明者们发现:在含有氰酸酯树脂、环氧树脂、潜在性固化剂及导电性填料的固化性树脂组合物中,通过使用具有活性氢的胺系潜在性固化剂作为潜在性固化剂,成为可得到导电性优异的固化物的固化性树脂组合物,从而完成了本发明。
本发明为一种固化性树脂组合物,其含有(A)氰酸酯树脂、(B)环氧树脂、(C)潜在性固化剂及(D)导电性填料,所述(C)潜在性固化剂含有使胺化合物与环氧化合物反应而得到的具有活性氢的胺系潜在性固化剂。
发明效果
根据本发明,能够提供可得到导电性、固化性优异的固化物的固化性树脂组合物。
附图说明
图1是实施例1的固化物的SEM图像。
图2是比较例3的固化物的SEM图像。
图3是实施例2的固化物的SEM图像。
图4是比较例1的固化物的SEM图像。
图5是实施例3的固化物的SEM图像。
具体实施方式
以下,对本发明的固化性树脂组合物进行说明。
本发明中使用的作为(A)成分的氰酸酯树脂只要是具有2个以上氰酸酯基的化合物即可,可以对分子结构、分子量等没有特别限制地使用。
作为上述氰酸酯树脂,例如可列举出下述式(1)所表示的化合物、下述式(2)所表示的化合物、以及它们的聚合物。
[化学式1]
NC-O-A1-Y1-A2-O-CN (1)
(式中,Y1表示非取代或被氟原子或氰氧基取代的2价的烃基、或者表示-O-、-S-或单键,A1及A2分别独立地表示非取代或被1~4个烷基取代的亚苯基。)
[化学式2]
(式中,m为1以上的整数,Y2及Y3分别独立地表示-S-、或者表示非取代或被氟原子或氰氧基取代的2价的烃基,R1、R2及R3分别独立地表示碳原子数1~4的烷基,n分别独立地为0~2的整数。)
作为上述式(1)中的Y1、以及上述式(2)中的Y2及Y3,例如可列举出下述式(Y-1)~(Y-9)所表示的基团。
[化学式3]
(式中,n为4~12的整数,R7及R8分别独立地表示氢原子或非取代或被氟原子取代的甲基。此外,*表示键合点。)
作为上述氰酸酯树脂的市售品,可列举出Lonza公司制的Cyanate LECy、PT-15、PT30、PT-60等、Huntsman公司制的L-10、XU366、XU371、XU378等、三菱瓦斯化学公司制的CA200等,但并不限定于这些。
这些氰酸酯树脂可以单独使用,也可以将2种以上并用。
上述氰酸酯树脂中,优选双酚型、联苯型及酚醛清漆苯酚型的氰酸酯树脂,特别优选双酚A型、双酚E型及双酚F型等双酚型氰酸酯树脂。
本发明中使用的作为(B)成分的环氧树脂只要是在分子中具有2个以上环氧基的树脂即可,可以对分子结构、分子量等没有特别限制地使用。
作为上述环氧树脂,可列举出氢醌、间苯二酚、焦儿茶酚、间苯三酚等单核多元酚化合物的聚缩水甘油醚化合物;二羟基萘、联苯酚、亚甲基双酚(双酚F)、亚甲基双(邻甲酚)、亚乙基双酚、异亚丙基双酚(双酚A)、异亚丙基双(邻甲酚)、四溴双酚A、1,3-双(4-羟基枯基苯)、1,4-双(4-羟基枯基苯)、1,1,3-三(4-羟基苯基)丁烷、1,1,2,2-四(4-羟基苯基)乙烷、硫代双酚、磺基双酚、氧代双酚、苯酚酚醛清漆、邻甲酚酚醛清漆、乙基苯酚酚醛清漆、丁基苯酚酚醛清漆、辛基苯酚酚醛清漆、间苯二酚酚醛清漆、萜烯酚等多核多元酚化合物的聚缩水甘油醚化合物;乙二醇、丙二醇、丁二醇、己二醇、聚乙二醇、聚丙二醇、硫甘醇、二环戊二烯二甲醇、2,2-双(4-羟基环己基)丙烷(氢化双酚A)、甘油、三羟甲基丙烷、季戊四醇、山梨糖醇、双酚A-环氧烷烃加成物等多元醇化合物的聚缩水甘油醚化合物;马来酸、富马酸、衣康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、偏苯三酸、均苯三甲酸、均苯四甲酸、四氢邻苯二甲酸、桥亚甲基四氢邻苯二甲酸等脂肪族、芳香族或脂环族多元酸的缩水甘油酯化合物及甲基丙烯酸缩水甘油酯的均聚物或共聚物;N,N-二缩水甘油基苯胺、双(4-(N-甲基-N-缩水甘油基氨基)苯基)甲烷、二缩水甘油基邻甲苯胺、N,N-双(2,3-环氧丙基)-4-(2,3-环氧丙氧基)-2-甲基苯胺、N,N-双(2,3-环氧丙基)-4-(2,3-环氧丙氧基)苯胺、N,N,N’,N’-四(2,3-环氧丙基)-4,4-二氨基二苯基甲烷等具有缩水甘油基氨基的环氧化合物;乙烯基环己烯二环氧化物、环戊二烯二环氧化物、3,4-环氧环己基甲基-3,4-环氧环己烷羧酸酯、3,4-环氧-6-甲基环己基甲基-6-甲基环己烷羧酸酯、双(3,4-环氧-6-甲基环己基甲基)己二酸酯等环状烯烃化合物的环氧化物;环氧化聚丁二烯、环氧化苯乙烯-丁二烯共聚物等环氧化共轭二烯聚合物;异氰脲酸三缩水甘油酯等杂环化合物。此外,这些环氧树脂也可以为通过末端异氰酸酯的预聚物而内部交联的环氧树脂、或以多价的活性氢化合物(多元酚、多胺、含羰基化合物、多磷酸酯等)高分子量化而成的环氧树脂。
这些环氧树脂可以单独使用,也可以将2种以上并用。
上述环氧树脂中,优选多核多元酚化合物的聚缩水甘油醚化合物。
作为(B)成分的环氧树脂的含量相对于作为(A)成分的氰酸酯树脂100质量份,优选为20~200质量份,为30~150质量份由于可得到优异的物性的固化物,因此更优选。
本发明中使用的作为(C)成分的潜在性固化剂含有使胺化合物与环氧化合物反应而得到的具有活性氢的胺系潜在性固化剂。
上述胺化合物是具有1个以上活性氢的胺化合物,例如可列举出乙二胺、1,2-二氨基丙烷、1,3-二氨基丙烷、1,3-二氨基丁烷、1,4-二氨基丁烷、六亚甲基二胺等亚烷基二胺类;二亚乙基三胺、三亚乙基三胺、四亚乙基五胺等多烷基多胺类;聚氧亚丙基二胺、聚氧亚丙基三胺等聚氧亚烷基多胺;1,4-二氨基环己烷、1,3-二氨基环己烷、1,3-二氨基甲基环己烷、1,2-二氨基环己烷、1,4-二氨基-3,6-二乙基环己烷、4,4’-二氨基二环己基甲烷、1,3-双(氨基甲基)环己烷、1,4-双(氨基甲基)环己烷、4,4’-二氨基二环己基丙烷、双(4-氨基环己基)砜、4,4’-二氨基二环己基醚、2,2’-二甲基-4,4’-二氨基二环己基甲烷、异佛尔酮二胺、降冰片烯二胺等脂环式多胺类;间苯二甲基二胺、二氨基二苯基甲烷、二氨基二苯基砜、二乙基甲苯二胺、1-甲基-3,5-二乙基-2,4-二氨基苯、1-甲基-3,5-二乙基-2,6-二氨基苯、1,3,5-三乙基-2,6-二氨基苯、3,3’-二乙基-4,4’-二氨基二苯基甲烷、3,5,3’、5’-四甲基-4,4’-二氨基二苯基甲烷等芳香族多胺类;苯并胍胺、乙酰胍胺等胍胺类;草酸二酰肼、丙二酸二酰肼、琥珀酸二酰肼、戊二酸二酰肼、己二酸二酰肼、辛二酸二酰肼、壬二酸二酰肼、癸二酸二酰肼、邻苯二甲酸二酰肼等二酰肼类;N,N-二甲基氨基乙基胺、N,N-二乙基氨基乙基胺、N,N-二异丙基氨基乙基胺、N,N-二烯丙基氨基乙基胺、N,N-苄基甲基氨基乙基胺、N,N-二苄基氨基乙基胺、N,N-环己基甲基氨基乙基胺、N,N-二环己基氨基乙基胺、N-(2-氨基乙基)吡咯烷、N-(2-氨基乙基)哌啶、N-(2-氨基乙基)吗啉、N-(2-氨基乙基)哌嗪、N-(2-氨基乙基)-N’-甲基哌嗪、N,N-二甲基氨基丙基胺、N,N-二乙基氨基丙基胺、N,N-二异丙基氨基丙基胺、N,N-二烯丙基氨基丙基胺、N,N-苄基甲基氨基丙基胺、N,N-二苄基氨基丙基胺、N,N-环己基甲基氨基丙基胺、N,N-二环己基氨基丙基胺、N-(3-氨基丙基)吡咯烷、N-(3-氨基丙基)哌啶、N-(3-氨基丙基)吗啉、N-(3-氨基丙基)哌嗪、N-(3-氨基丙基)-N’-甲基哌啶、4-(N,N-二甲基氨基)苄基胺、4-(N,N-二乙基氨基)苄基胺、4-(N,N-二异丙基氨基)苄基胺、N,N-二甲基异佛尔酮二胺、N,N-二甲基双氨基环己烷、N,N,N’-三甲基乙二胺、N’-乙基-N,N-二甲基乙二胺、N,N,N’-三甲基乙二胺、N’-乙基-N,N-二甲基丙二胺、N’-乙基-N,N-二苄基氨基丙基胺;N,N-(双氨基丙基)-N-甲基胺、N,N-双氨基丙基乙基胺、N,N-双氨基丙基丙基胺、N,N-双氨基丙基丁基胺、N,N-双氨基丙基戊基胺、N,N-双氨基丙基己基胺、N,N-双氨基丙基-2-乙基己基胺、N,N-双氨基丙基环己基胺、N,N-双氨基丙基苄基胺、N,N-双氨基丙基烯丙基胺、双〔3-(N,N-二甲基氨基丙基)〕胺、双〔3-(N,N-二乙基氨基丙基)〕胺、双〔3-(N,N-二异丙基氨基丙基)〕胺、双〔3-(N,N-二丁基氨基丙基)〕胺等。
胺化合物的活性氢当量从固化性与贮藏稳定性的平衡的方面出发优选为10以上且300以下,更优选为15以上且150以下。
上述胺化合物中,使用选自脂肪族胺及脂环式胺中的1种以上从固化性优异的方面出发优选。具体而言,作为尤其优选的例子,可列举出乙二胺、1,2-亚丙基二胺等亚烷基二胺;二亚乙基三胺、三亚乙基四胺等聚亚烷基多胺;二氧亚丙基二胺、聚氧亚丙基多胺、聚氧亚乙基多胺等聚氧亚烷基多胺;异佛尔酮二胺、1,3-二氨基甲基环己烷、N-(2-氨基乙基)哌嗪等脂环式胺等。特别优选1,2-亚丙基二胺、二氧亚丙基二胺、N-(2-氨基乙基)哌嗪。
作为上述环氧化合物,例如可列举出氢醌、间苯二酚、焦儿茶酚、间苯三酚等单核多元酚化合物的聚缩水甘油醚化合物;二羟基萘、联苯酚、亚甲基双酚(双酚F)、亚甲基双(邻甲酚)、亚乙基双酚、异亚丙基双酚(双酚A)、异亚丙基双(邻甲酚)、四溴双酚A、1,3-双(4-羟基枯基苯)、1,4-双(4-羟基枯基苯)、1,1,3-三(4-羟基苯基)丁烷、1,1,2,2-四(4-羟基苯基)乙烷、硫代双酚、磺酰基双酚、氧代双酚、苯酚酚醛清漆、邻甲酚酚醛清漆、乙基苯酚酚醛清漆、丁基苯酚酚醛清漆、辛基苯酚酚醛清漆、间苯二酚酚醛清漆、萜烯酚等多核多元酚化合物的聚缩水甘油醚化合物;乙二醇、丙二醇、丁二醇、己二醇、聚乙二醇、硫代二甘醇、甘油、三羟甲基丙烷、季戊四醇、山梨糖醇、双酚A-环氧烷烃加成物等多元醇类的聚缩水甘油醚;马来酸、富马酸、衣康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、偏苯三酸、均苯三甲酸、均苯四甲酸、四氢邻苯二甲酸、六氢邻苯二甲酸、桥亚甲基四氢邻苯二甲酸等脂肪族、芳香族或脂环族多元酸的缩水甘油酯类及甲基丙烯酸缩水甘油酯的均聚物或共聚物;N,N-二缩水甘油基苯胺、双(4-(N-甲基-N-缩水甘油基氨基)苯基)甲烷、二缩水甘油基邻甲苯胺等具有缩水甘油基氨基的环氧化合物;乙烯基环己烯二环氧化物、二环戊二烯二环氧化物、3,4-环氧环己基甲基-3,4-环氧环己烷羧酸酯、3,4-环氧-6-甲基环己基甲基-6-甲基环己烷羧酸酯、双(3,4-环氧-6-甲基环己基甲基)己二酸酯等环状烯烃化合物的环氧化物;环氧化聚丁二烯、环氧化苯乙烯-丁二烯共聚物等环氧化共轭二烯聚合物、异氰脲酸三缩水甘油酯等杂环化合物。
上述环氧化合物可以为缩水甘油基型环氧化合物及以环状烯烃化合物的环氧化物为代表的氧化环烯烃型的环氧化合物中的任一种。此外在为缩水甘油基型的情况下,可以为具有芳香族环的芳香族环氧化合物及不具有芳香族环的脂肪族环氧化合物中的任一种。从反应性的方面出发,优选使用缩水甘油基型的环氧化合物,从耐热性的方面出发,更优选使用缩水甘油基型的芳香族环氧化合物。
上述胺系潜在性固化剂是使胺化合物与环氧化合物反应而得到的物质,优选为相对于胺化合物的活性氢1当量使环氧化合物的环氧基成为0.1~0.9当量的量、特别是成为0.2~0.8当量的量反应而得到的物质。
通过将环氧化合物相对于胺化合物的量设定为上述下限值以上,能够提高固化性树脂组合物的保存稳定性,因此优选,通过设定为上述上限值以下,能够可靠地得到固化性,因此优选。
上述胺系潜在性固化剂的制造方法没有特别限定,但可列举出根据需要使用溶剂在常温~140℃的加热下反应1~10小时的方法。在使用溶剂的情况下,也可以在反应结束后将溶剂在加热下通过常压或减压而除去。
作为上述胺系潜在性固化剂的制造中使用的溶剂,可列举出甲乙酮、甲基戊基酮、二乙基酮、丙酮、甲基异丙基酮、丙二醇单甲基醚乙酸酯、环己烷等酮类;四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、丙二醇单甲基醚等醚类;乙酸乙酯、乙酸正丁酯等酯类;苯、甲苯、二甲苯等芳香族烃;四氯化碳、氯仿、三氯乙烯、二氯甲烷等卤代脂肪族烃;氯苯等卤代芳香族烃。
本发明中使用的作为(C)成分的潜在性固化剂进一步含有酚醛树脂由于能够提高稳定性,因此优选。
作为上述酚醛树脂,例如可列举出苯酚酚醛清漆树脂、甲酚酚醛清漆树脂、芳香族烃甲醛树脂改性酚醛树脂、二环戊二烯苯酚加成型树脂、苯酚芳烷基树脂(Xylok resin)、萘酚芳烷基树脂、三苯酚基甲烷树脂、四苯酚基乙烷树脂、萘酚酚醛清漆树脂、萘酚-苯酚共缩合酚醛清漆树脂、萘酚-甲酚共缩合酚醛清漆树脂、联苯改性酚醛树脂(苯酚核通过双亚甲基连接而成的多元酚化合物)、联苯改性萘酚树脂(苯酚核通过双亚甲基连接而成的多元萘酚化合物)、氨基三嗪改性酚醛树脂(在分子结构中具有苯酚骨架、三嗪环及伯氨基的化合物)及含烷氧基的芳香环改性酚醛清漆树脂(苯酚核及含烷氧基的芳香环通过甲醛连接而成的多元酚化合物)等多元酚化合物。
本发明中,从得到固化性树脂组合物的贮藏稳定性与固化性的平衡优异的组合物的观点出发,作为酚醛树脂,优选使用软化点为50~200℃的酚醛树脂。
上述酚醛树脂的使用量相对于上述胺系潜在性固化剂100质量份,优选为10~100质量份,特别优选为20~60质量份。通过设定为10质量份以上,可得到充分的固化性,通过设定为100质量份以下,能够更可靠地避免固化物的物性的降低,因此优选。
在本发明中使用的作为(C)成分的潜在性固化剂为固体的情况下,也可以使用利用喷射磨等粉碎机进行粉碎而得到的物质。
上述潜在性固化剂也可以含有上述胺系潜在性固化剂及酚醛树脂以外的其他的潜在性固化剂。作为其他的潜在性固化剂,例如可列举出草酸二酰肼、丙二酸二酰肼、琥珀酸二酰肼、戊二酸二酰肼、己二酸二酰肼、辛二酸二酰肼、壬二酸二酰肼、癸二酸二酰肼、邻苯二甲酸二酰肼等二元酸二酰肼;双氰胺、苯并胍胺、乙酰胍胺等胍化合物;三聚氰胺;胺与羧酸的脱水缩合物、胺与异氰酸酯的加成物、胺的麦克尔加成物、胺的曼尼希反应物、胺与尿素的缩合物、胺与酮的缩合物等改性胺等。但是,在使用它们的情况下,有可能降低导电性,因此优选在潜在性固化剂中不超过50质量%。
作为(C)成分的潜在性固化剂的含量没有特别限定,但从反应性、单组分稳定性的理由出发,相对于作为(A)成分的氰酸酯树脂及作为(B)成分的环氧树脂的合计量100质量份,优选为1~70质量份,更优选为3~60质量份。
本发明中使用的作为(D)成分的导电性填料只要是具有导电性的物质即可,例如可列举出金、银、镍、铜、焊料等金属粒子;氧化锡、氧化铟、氧化锌等金属氧化物;炭黑、石墨、碳纳米管、碳纤维等碳系等,还可列举出进一步在非金属的玻璃、陶瓷、塑料等上被覆上述导电性层等而得到的物质。从进入间隙的容易性、熔融性优异、并且导电性赋予效果充分的观点出发,它们的平均粒径优选为0.1~50μm,特别优选为0.5~30μm。这里平均粒径的测定使用利用激光衍射的粒径分布测定装置来测定。
此外,粒子的形状可列举出球状、扁平状、板状、片状、薄片状、棒状、树枝状、纤维状、针状、鳞片状、角状、多面体状等,但没有特别限定。
作为(D)成分的导电填料的含量从导电性赋予效果充分的观点出发,在固化性树脂组合物中优选为30~90质量%,特别优选为50~80质量%。
需要说明的是,就在环氧树脂和氰酸酯树脂中配合使胺化合物与环氧化合物反应而得到的具有活性氢的潜在性固化剂和导电性填料的体系而言,认为在固化而成的固化物中产生导电性填料的局部化(参照图1~图4的SEM图像),通过导电通路形成及增加而导电性提高。在不使用氰酸酯树脂的情况或使用不具有活性氢的胺系潜在性固化剂的情况下,观察不到局部化。
本发明中,可以根据需要并用公知的固化促进剂。作为这些固化促进剂的具体例子,可例示出三苯基膦等膦类;四苯基溴化鏻等鏻盐;2-甲基咪唑、2-苯基咪唑、2-乙基-4-甲基咪唑、2-十一烷基咪唑、1-氰基乙基-2-甲基咪唑等咪唑类;上述咪唑类与偏苯三酸、异氰脲酸、硼等的盐即咪唑盐类;苄基二甲基胺、2,4,6-三(二甲基氨基甲基)苯酚等胺类;三甲基氯化铵等季铵盐类;3-(对氯苯基)-1,1-二甲基脲、3-(3,4-二氯苯基)-1,1-二甲基脲、3-苯基-1,1-二甲基脲、异佛尔酮二异氰酸酯-二甲基脲、甲苯二异氰酸酯-二甲基脲等脲类;及三氟化硼与胺类或醚化合物等的络合物等。这些固化促进剂可以单独使用,也可以将2种以上并用。固化促进剂的含量没有特别限制,可以根据用途等适宜设定。
在本发明的固化性树脂组合物中,可以根据需要含有各种添加剂。作为添加剂,可列举出联苯酚等酚类化合物;对叔丁基缩水甘油醚、正丁基缩水甘油醚、C12~13混合醇缩水甘油醚等反应性稀释剂;邻苯二甲酸二辛酯、邻苯二甲酸二丁酯、苄基醇、煤焦油等非反应性的稀释剂(增塑剂);熔融二氧化硅、结晶二氧化硅等二氧化硅;氧化铝(矾土)、氧化镁、氧化锌、氢氧化镁、氢氧化铝、氮化铝、氮化硅、氮化硼、钼酸锌、碳酸钙、碳酸硅、硅酸钙、钛酸钾、氧化铍、氧化锆、锆石、镁橄榄石、块滑石、尖晶石、莫来石、氧化钛等粉体或将它们球形化而得到的珠、及玻璃纤维、纸浆纤维、合成纤维、陶瓷纤维等填充剂;玻璃布、芳纶布、碳纤维等增强材料;颜料;γ-氨基丙基三乙氧基硅烷、N-β-(氨基乙基)-γ-氨基丙基三乙氧基硅烷、N-β-(氨基乙基)-N’-β-(氨基乙基)-γ-氨基丙基三乙氧基硅烷、γ-苯胺基丙基三乙氧基硅烷、γ-环氧丙氧基丙基三乙氧基硅烷、β-(3,4-环氧环己基)乙基三乙氧基硅烷、乙烯基三乙氧基硅烷、N-β-(N-乙烯基苄基氨基乙基)-γ-氨基丙基三乙氧基硅烷、γ-甲基丙烯酰氧基丙基三甲氧基硅烷、γ-氯丙基三甲氧基硅烷、γ-巯基丙基三甲氧基硅烷等硅烷偶联剂;小烛树蜡、巴西棕榈蜡、木蜡、白蜡、蜂蜡、羊毛脂、鲸蜡、褐煤蜡、石油蜡、脂肪族蜡、脂肪族酯、脂肪族醚、芳香族酯、芳香族醚等润滑剂;增稠剂;触变剂;抗氧化剂;光稳定剂;紫外线吸收剂;消泡剂;防锈剂;胶体二氧化硅、胶体氧化铝等常用的添加剂。
进而,也可以并用二甲苯树脂、石油树脂等粘合性的树脂类。
在使本发明的固化性树脂组合物固化的情况下,例如在80~200℃下进行加热由于发挥作为固化物的物性,因此优选。
本发明的固化性树脂组合物可以作为粘接剂用于广泛的用途。特别是由于固化物的导电性优异,因此可以适宜用于半导体密封、电子部件的粘接剂等电子用途。
实施例
接着,通过实施例及比较例对本发明更详细地进行说明,但本发明不受这些实施例的任何限定。
[制造例1](潜在性固化剂EH-1的合成)
在烧瓶中投入1,2-二氨基丙烷201g并加温至60℃后,按照***内温度保持在100~110℃的方式一点点地添加Adeka Resin EP-4100E(株式会社艾迪科的商品名;以双酚A型环氧树脂计环氧当量为190)580g[Adeka Resin EP-4100E相对于1,2-二氨基丙烷1摩尔的环氧当量;1.12]。将Adeka Resin EP-4100E全部添加后,将反应体系升温至140℃并反应1.5小时,得到具有活性氢的胺系潜在性固化剂。接着,相对于所得到的具有活性氢的胺系潜在性固化剂100g投入MP-800K(旭有机材(株式会社)制;酚醛树脂、软化点100℃)30g,以180~190℃、30~40托的条件用1小时利用减压脱气来除去未反应物、溶剂,使用喷射磨进行粉碎,得到潜在性固化剂(EH-1)。
[制造例2](潜在性固化剂EH-2的合成)
在烧瓶中投入异佛尔酮二胺352g并加温至60℃后,按照***内温度保持在100~110℃的方式一点点地添加Adeka Resin EP-4100E(株式会社艾迪科的商品名;以双酚A型环氧树脂计环氧当量为190)580g[Adeka Resin EP-4100E相对于异佛尔酮二胺1摩尔的环氧当量;1.47]。将Adeka Resin EP-4100E全部添加后,将反应体系升温至140℃并反应1.5小时,得到具有活性氢的胺系潜在性固化剂。接着,相对于所得到的具有活性氢的胺系潜在性固化剂100g投入MP-800K(旭有机材(株式会社)制;酚醛树脂、软化点100℃)30g,以180~190℃、30~40托的条件用1小时利用减压脱气来除去未反应物、溶剂,使用喷射磨进行粉碎,得到潜在性固化剂(EH-2)。
[制造例3](潜在性固化剂EH-3的合成)
在烧瓶中投入2-乙基-4-甲基咪唑190g并加温至60℃后,按照***内温度保持在100~110℃的方式一点点地添加Adeka Resin EP-4100E(株式会社艾迪科的商品名;以双酚A型环氧树脂计环氧当量为190)409g[2-乙基-4-甲基咪唑的活性氢当量:上述AdekaResin EP-4100E的环氧当量;1:1.24]。将Adeka Resin EP-4100E全部添加后,将反应体系升温至140℃并反应1.5小时,得到不具有活性氢的改性咪唑。接着,相对于所得到的改性咪唑100g,投入MP-800K(旭有机材(株式会社)制;酚醛树脂、软化点100℃)30g,以180~190℃、30~40托的条件用1小时利用减压脱气来除去未反应物、溶剂,使用喷射磨进行粉碎,得到潜在性固化剂(EH-3)。
[实施例1~4及比较例1~3]
按照下述表1中记载的配方将各成分混合而制造树脂组合物,进行下述试验。对于评价结果,示于下述表1中。需要说明的是,表1中记载的配合的数值表示质量份。
表1
EP-1:株式会社艾迪科制EP-4901E(双酚F型环氧树脂)
EP-2:株式会社艾迪科制ED-509S(4-叔丁基苯基缩水甘油醚)
CY-1:Lonza公司制LECy(双酚型氰酸酯树脂)
EH-1:制造例1中制造的潜在性固化剂(EH-1)
EH-2:制造例2中制造的潜在性固化剂(EH-2)
EH-3:制造例3中制造的潜在性固化剂(EH-3)
EH-4:双氰胺
KBM-403:信越化学工业(株式会社)制KBM-403(3-环氧丙氧基丙基三甲氧基硅烷)
Ag-1:平均粒径4.8μm的扁平状的银粒子
Ag-2:平均粒径0.9μm的球状的银粒子
Ag-3:平均粒径1.0μm的树枝状电解银粉
Ag/Cu-1:平均粒径6.0μm的扁平状的镀银铜粉
<导电性>
将实施例及比较例的固化性树脂组合物按照厚度成为100~300μm的方式通过棒涂机涂布于玻璃板上。在保持于150℃的循环式恒温槽中加热30分钟而固化。测定所得到的固化膜的膜厚,并且作为导电性的评价,测定体积电阻率。对于体积电阻率(Ω·cm),利用4端子4探针法电阻率计(Loresta GPMPC-T610、Mitsubishi Chemical Analytech公司制)来算出。
将电阻值为1.0×10-2Ω·cm以下的情况设定为A,将电阻值超过1.0×10-2Ω·cm的情况设定为B。
<胶凝时间>
将热板的温度设定为150±2℃,将实施例及比较例的固化性组合物约1g放置于该热板上,一边将其搅拌一边测定直至变得无法搅拌为止的时间(胶凝时间)。
将胶凝时间低于10秒的情况设定为A,将10秒以上的情况设定为B。
<SEM图像>
对于由上述实施例及比较例的固化性树脂组合物得到的固化物,使用SEM来观察玻璃板上的固化涂膜。
图1是将实施例1的固化物放大4000倍而得到的图像,图2是将比较例3的固化物放大4000倍而得到的图像,图3是将实施例2的固化物放大2000倍而得到的图像,图4是将比较例1的固化物放大2000倍而得到的图像。分别通过将图1与图2、图3与图4进行比较,在实施例1及2中见到银的局部化,认为形成导电通路而导电性提高。图5是将实施例3的固化物放大2000倍而得到的图像,与实施例1及2同样地见到银的局部化。
如上述实施例中所示的那样,本发明的固化性树脂组合物是可得到导电性、固化性优异的固化物的固化性树脂组合物。
产业上的可利用性
根据本发明,特别是由于能够提供可得到导电性优异的固化物的固化性树脂组合物,因此例如可以适宜用于焊料代替材料等导电性材料。
Claims (10)
1.一种固化性树脂组合物,其含有(A)氰酸酯树脂、(B)环氧树脂、(C)潜在性固化剂及(D)导电性填料,所述(C)潜在性固化剂含有使胺化合物与环氧化合物反应而得到的具有活性氢的胺系潜在性固化剂。
2.根据权利要求1所述的固化性树脂组合物,其中,作为(A)成分的氰酸酯树脂为从下述式(1)所表示的化合物、下述式(2)所表示的化合物、以及选自它们中的至少1种化合物的聚合物中选择的1种以上,
N(OAOCN(1)
式中,Y1表示非取代或被氟原子或氰氧基取代的2价的烃基、或者表示-O-、-S-或单键,A1及A2分别独立地表示非取代或被1~4个烷基取代的亚苯基,
式中,m为1以上的整数,Y2及Y3分别独立地表示-S-、或者表示非取代或被氟原子或氰氧基取代的2价的烃基,R1、R2及R3分别独立地表示碳原子数1~4的烷基,n分别独立地为0~2的整数。
3.根据权利要求2所述的固化性树脂组合物,其中,所述式(1)中的Y1、以及所述式(2)中的Y2及Y3分别独立地为选自下述式(Y-1)~(Y-9)中的1种以上,
式中,n为4~12的整数,R7及R8分别独立地表示氢原子或非取代或被氟原子取代的甲基,而且,*表示键合点。
4.根据权利要求1~3中任一项所述的固化性树脂组合物,其中,(C)成分中的胺化合物为选自脂肪族胺及脂环式胺中的1种以上。
5.根据权利要求1~4中任一项所述的固化性树脂组合物,其中,作为(C)成分的潜在性固化剂进一步含有酚醛树脂。
6.根据权利要求1~5中任一项所述的固化性树脂组合物,其中,作为(D)成分的导电性填料为选自银粒子及铜粒子中的1种以上。
7.根据权利要求1~6中任一项所述的固化性树脂组合物,其中,作为(D)成分的导电填料的粒径为0.1~50μm。
8.根据权利要求1~7中任一项所述的固化性树脂组合物,其中,作为(D)成分的导电填料的含量在固化性树脂组合物中为30~90质量%。
9.一种固化物,其是将权利要求1~8中任一项所述的固化性树脂组合物固化而得到的。
10.一种粘接剂,其包含权利要求1~8中任一项所述的固化性树脂组合物。
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