CN105793361A - 树脂组合物、导热性固化物、硅化合物、硅烷偶联剂组合物和负载体 - Google Patents
树脂组合物、导热性固化物、硅化合物、硅烷偶联剂组合物和负载体 Download PDFInfo
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- CN105793361A CN105793361A CN201480066236.3A CN201480066236A CN105793361A CN 105793361 A CN105793361 A CN 105793361A CN 201480066236 A CN201480066236 A CN 201480066236A CN 105793361 A CN105793361 A CN 105793361A
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- H—ELECTRICITY
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Abstract
提供能够制造具有优异的导热性的导热性固化物的树脂组合物。一种树脂组合物,其含有:负载有硅烷偶联剂组合物的负载体,硅烷偶联剂组合物含有下述通式(1)所示的硅化合物。(通式(1)中,R1分别独立地表示碳原子数1~3的直链或支链状的烷基,A1表示单键或碳原子数1~4的烷二基,Y表示氢原子、碳原子数1~12的直链或支链状的烷基等)。
Description
技术领域
本发明涉及树脂组合物、使该树脂组合物固化而得到的导热性固化物、具有特定结构的新型硅化合物、含有该硅化合物的硅烷偶联剂组合物和负载有该硅烷偶联剂组合物的负载体。
背景技术
近年来,伴随着电子设备、电子仪器的高速化和高功能化,半导体元件、功率晶体管等电子部件有高集成化且高密度化的倾向。然而,使电子部件高集成化和高密度化时,存在消耗电力增大,放热量增加这样的问题。在电子部件内部中产生的热有时引起电子部件的劣化、错误动作等不良情况。
作为抑制这样的不良情况的方法,有各种报道。例如,作为从电子部件除去热的方法,已知有使用以冷却风扇为代表的冷却用部件强制地进行空气冷却的方法。另外,已知有:涂布硅脂进行散热的方法;使用导热性片使热从电子部件传递至冷却用部件的方法。
作为使热从电子部件效率良好地传递至冷却用部件的方法中使用的导热性片,报道了各种物质。例如,专利文献1中公开了,使用含有环氧树脂、固化剂、填料、表面处理剂和溶剂的树脂组合物形成的导热性环氧树脂片材。另外,专利文献2中公开了,含有硅系共聚物和导热性填料的导热片、以及作为导热性填料优选氮化铝、氧化铝和氮化硼。进而,专利文献2中公开了,含有硅烷偶联剂时,导热性填料的分散性、硅系共聚物与导热性填料的密合性提高。
现有技术文献
专利文献
专利文献1:日本特开2010-007039号公报
专利文献2:日本特开2010-229269号公报
发明内容
发明要解决的问题
作为用于使热从电子部件效率良好地传递至冷却用部件的导热性片,使用片状的导热性固化物时,要求该导热性固化物具有高导热性。以往,为了提高导热性固化物的导热性,对于填料的种类、其含量进行了研究,但无法得到具有所期望的导热性的导热性固化物。因此,期望开发出能够有效地提高导热性固化物的导热性的添加剂等。
用于解决问题的方案
本发明人等反复研究,结果发现:使含有负载有硅烷偶联剂组合物的负载体的树脂组合物固化而得到的固化物显示出特别优异的导热性,所述硅烷偶联剂组合物含有具有特定结构的硅化合物,从而完成了本发明。
即,本发明提供如下树脂组合物:含有负载有硅烷偶联剂组合物的负载体,前述硅烷偶联剂组合物含有下述通式(1)所示的硅化合物。进而,本发明提供使该树脂组合物固化而得到的导热性固化物。
(前述通式(1)中,R1分别独立地表示碳原子数1~3的直链或支链状的烷基,A1表示单键或碳原子数1~4的烷二基,Y表示氢原子、碳原子数1~12的直链或支链状的烷基、碳原子数1~12的直链或支链状的氧基烷基、二甲基氨基、二乙基氨基或乙基甲基氨基。X表示下述式(X-1)~(X-6)中的任一者所示的基团,X是下述式(X-1)所示基团的情况下的Z为-NHCO-,X是下述式(X-2)~(X-6)中的任一者所示基团的情况下的Z为单键或-NHCO-)
另外,本发明提供:下述通式(2)所示的硅化合物;含有该硅化合物的硅烷偶联剂组合物;和负载有该硅烷偶联剂组合物的负载体。
(前述通式(2)中,R1分别独立地表示碳原子数1~3的直链或支链状的烷基,A2表示碳原子数1~4的烷二基,X表示下述式(X-1)~(X-6)中的任一者所示的基团,Y表示氢原子、碳原子数1~12的直链或支链状的烷基、碳原子数1~12的直链或支链状的氧基烷基、二甲基氨基、二乙基氨基或乙基甲基氨基)。
发明的效果
根据本发明,可以提供能够制造具有优异的导热性的导热性固化物的树脂组合物。另外,根据本发明,可以提供具有优异的导热性的导热性固化物。进而,根据本发明,可以提供新型的硅化合物。如果使用该新型的硅化合物,则可以提供能够制造具有特别优异的导热性的导热性固化物的树脂组合物中使用的负载体。
具体实施方式
本说明书中的“负载”也指的是,化学键(例如共价键、电子价键合和离子键等)、范德华力、静电力、附着、吸附、固着和其他种类的缔合等硅烷偶联剂组合物与被负载体的所有形态的结合。
本发明的树脂组合物含有负载有硅烷偶联剂组合物的负载体。而且,硅烷偶联剂组合物含有下述通式(1)所示的硅化合物。
(前述通式(1)中,R1分别独立地表示碳原子数1~3的直链或支链状的烷基,A1表示单键或碳原子数1~4的烷二基,Y表示氢原子、碳原子数1~12的直链或支链状的烷基、碳原子数1~12的直链或支链状的氧基烷基、二甲基氨基、二乙基氨基或乙基甲基氨基。X表示下述式(X-1)~(X-6)中的任一者所示的基团,X是下述式(X-1)所示基团的情况下的Z为-NHCO-,X是下述式(X-2)~(X-6)中的任一者所示基团的情况下的Z为单键或-NHCO-)。
上述通式(1)中,R1分别独立地表示碳原子数1~3的直链或支链状的烷基。作为碳原子数1~3的直链或支链状的烷基,可以举出:甲基、乙基、丙基和异丙基。
上述通式(1)中,A1表示单键或碳原子数1~4的烷二基。作为碳原子数1~4的烷二基,可以举出:亚甲基、亚乙基、亚丙基和亚丁基。
上述通式(1)中,X表示上述式(X-1)~(X-6)中的任一者所示的基团。而且,X是式(X-1)所示基团的情况下的Z为-NHCO-。另外,X是式(X-2)~(X-6)所示基团的情况下的Z为单键或-NHCO-。
上述通式(1)中,Y表示氢原子、碳原子数1~12的直链或支链状的烷基、碳原子数1~12的直链或支链状的氧基烷基、二甲基氨基、二乙基氨基或乙基甲基氨基。作为碳原子数1~12的直链或支链状的烷基,可以举出:甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基(pentylgroup)、戊基(amylgroup)、异戊基、己基、庚基、异庚基、辛基、异辛基、2-乙基己基、壬基、异壬基、癸基和十二烷基等。另外,作为碳原子数1~12的直链或支链状的氧基烷基,可以举出:甲基氧基、乙基氧基、丙基氧基、异丙基氧基、丁基氧基、仲丁基氧基、叔丁基氧基、异丁基氧基、戊基氧基、异戊基氧基、叔戊基氧基、己基氧基、环己基氧基、庚基氧基、异庚基氧基、叔庚基氧基、正辛基氧基、异辛基氧基、叔辛基氧基和2-乙基己基氧基等。
上述通式(1)中的Z优选为-NHCO-。使用通式(1)中的Z为-NHCO-的硅化合物时,可以大幅提高所得导热性固化物的导热率。另外,通式(1)中的A1为亚丙基的情况下,从经济方面出发优选。
作为通式(1)所示的硅化合物的优选具体例,可以举出:下述化学式No.1~No.99所示的化合物No.1~No.99。需要说明的是,下述化学式中的“Me”表示甲基,“Et”表示乙基。通式(1)所示的硅化合物中有时存在偶氮基所引起的2个几何异构体。本发明中,不将它们进行区别,可以为1个几何异构体也可以为2个几何异构体的混合物。
通式(1)所示的硅化合物可以应用公知的反应来制造,对其制造方法没有任何限定。通式(1)中的Z为单键的硅化合物例如可以如下制造:使与目标化合物对应的结构的苯基化合物和三烷氧基硅烷在以六氯铂(IV)酸等为代表的催化剂存在下反应从而制造。另外,通式(1)中的Z为-NHCO-的硅化合物例如可以如下制造:使与目标化合物对应的结构的羧酸和以3-氨基丙基三烷氧基硅烷为代表的具有氨基的三烷氧基硅烷在碱性下、与以O-(苯并三唑-1-基)-N,N,N’,N’-四甲基脲六氟磷酸酯为代表的缩合剂一起反应从而制造。
本发明的树脂组合物通常含有:负载有硅烷偶联剂组合物的负载体30~80质量%和树脂成分20~70质量%(其中,负载体+树脂成分=100质量%)。
本发明的树脂组合物例如是使含有通式(1)所示的硅化合物的硅烷偶联剂组合物负载于被负载体而得到的。作为使硅烷偶联剂组合物负载在被负载体中的方法,可以使用公知的方法。例如,可以使用气层吸附、液层吸附等方法。需要说明的是,作为液层吸附的例子,可以举出:通过使被负载体浸渍于在溶剂中溶解通式(1)所示的硅化合物而得到的溶液,从而使硅化合物吸附于被负载体的方法。
树脂成分的种类没有特别限定。作为树脂成分,例如可以举出:热固化性树脂、热塑性树脂。其中,优选使用热固化性树脂。作为热固化性树脂,例如可以举出:氨基树脂、氰酸酯树脂、异氰酸酯树脂、聚酰亚胺、环氧树脂、氧杂环丁烷树脂、聚酯、烯丙基树脂、酚醛树脂、苯并噁嗪树脂、二甲苯树脂、酮树脂、呋喃树脂、COPNA树脂、有机硅树脂、二环戊二烯树脂、苯并环丁烯树脂、环硫化物树脂、烯-硫醇树脂、聚甲亚胺树脂、聚乙烯基苄基醚、苊烯等。其中,作为树脂成分,优选氰酸酯树脂、异氰酸酯树脂、环氧树脂、酚醛树脂。
作为氰酸酯树脂,例如有:使卤代氰化合物与苯酚类、萘酚类反应,根据需要进行加热等进行预聚物化而得到的氰酸酯树脂等。作为氰酸酯树脂,例如可以举出:酚醛清漆型氰酸酯树脂、双酚A型氰酸酯树脂、双酚E型氰酸酯树脂、四甲基双酚F型氰酸酯树脂等双酚型氰酸酯树脂和萘酚芳烷基型氰酸酯树脂等。更具体而言,可以举出:2,2’-双(4-氰酸根合苯基)异丙叉、1,1’-双(4-氰酸根合苯基)乙烷、双(4-氰酸根合-3,5-二甲基苯基)甲烷、1,3-双(4-氰酸根合苯基-1-(1-甲基乙叉基))苯、二环戊二烯型氰酸酯、苯酚酚醛清漆型氰酸酯、双(4-氰酸根合苯基)硫醚、双(4-氰酸根合苯基)醚、1,1,1-三(4-氰酸根合苯基)乙烷、三(4-氰酸根合苯基)亚磷酸酯、双(4-氰酸根合苯基)砜、2,2-双(4-氰酸根合苯基)丙烷、1,3-二氰酸根合萘、1,4-二氰酸根合萘、1,6-二氰酸根合萘、1,8-二氰酸根合萘、2,6-二氰酸根合萘或2,7-二氰酸根合萘、1,3,6-三氰酸根合萘、4,4-二氰酸根合联苯、和由苯酚酚醛清漆型、甲酚酚醛清漆型的多元酚类与卤代氰的反应得到的氰酸酯树脂;由萘酚芳烷基型多元萘酚类与卤代氰反应得到的氰酸酯树脂等。
作为异氰酸酯树脂,例如有:通过苯酚类和卤代氰的脱卤化氢反应而得到的异氰酸酯树脂。作为异氰酸酯树脂,例如可以举出:4,4’-二苯基甲烷二异氰酸酯MDI、多亚甲基多苯基多异氰酸酯、甲苯二异氰酸酯、六亚甲基二异氰酸酯等。
作为环氧树脂,例如可以举出:氢醌、间苯二酚、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)、乙叉基双酚、异丙叉基双酚(双酚A)、异丙叉基双(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、氧基双酚、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、硫二甘醇、丙三醇、三羟甲基丙烷、季戊四醇、山梨糖醇、双酚A-环氧乙烷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、均苯三酸、均苯四酸、四氢邻苯二甲酸、六氢邻苯二甲酸、内亚甲基四氢邻苯二甲酸等的脂肪族、芳香族或脂环族多元酸的缩水甘油酯类、和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、二环戊烷二烯二环氧化物、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。其中,优选萘型环氧、双酚A型环氧。
作为酚醛树脂,有:由酚类和醛类合成的酚醛树脂。作为酚类,例如可以举出:苯酚、甲酚、乙基苯酚、正丙基苯酚、异丙基苯酚、丁基苯酚、叔丁基苯酚、辛基苯酚、壬基苯酚、十二烷基苯酚、环己基苯酚、氯苯酚、溴苯酚、间苯二酚、邻苯二酚、氢醌、2,2-双(4-羟基苯基)丙烷、4,4’-硫代二苯酚、二羟基二苯基甲烷、萘酚、萜烯酚、苯酚化二环戊二烯等。另外,作为醛类,可以举出:甲醛。
本发明的树脂组合物中可以根据需要添加各种添加物。作为添加物,例如可以举出:环氧树脂中使用的固化剂;天然蜡类、合成蜡类、长链脂肪族酸的金属盐类等增塑剂;酰胺类、酯类、石蜡类等脱模剂;丁腈橡胶、丁二烯橡胶等应力松弛剂;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、溴化苯酚酚醛清漆等溴系阻燃剂;磷系阻燃剂;染料、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、增粘剂、抗静电剂、润滑剂、紫外线吸收剂等。进而,还可以配混醇类、醚类、醛缩类、酮类、酯类、醇酯类、酮醇类、醚醇类、酮醚类、酮酯类、酯醚类、芳香族系溶剂等有机溶剂等。
作为环氧树脂中使用的固化剂,可以举出:潜在性固化剂、酸酐、多胺化合物、多元酚化合物和阳离子系光引发剂等。
作为潜在性固化剂,可以举出:双氰胺、酰肼、咪唑化合物、胺加合物、锍盐、鎓盐、酮亚胺、酸酐、叔胺等。使用这些潜在性固化剂时,可以将本发明的树脂组合物制成容易操作的一液型的固化性组合物,故优选。
作为酸酐,可以举出: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,可以举出:乙二胺、二亚乙基三胺、三亚乙基四胺等脂肪族多胺;薄荷烷二胺、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;间二甲苯二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。
作为多元酚化合物,可以举出:苯酚酚醛清漆、邻甲酚酚醛清漆、叔丁基苯酚酚醛清漆、二环戊二烯甲酚、萜烯二苯酚、萜烯二邻苯二酚、1,1,3-三(3-叔丁基-4-羟基-6-甲基苯基)丁烷、丁叉基双(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。
作为咪唑化合物,可以举出: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-均三嗪、2,4-二氨基-6(2’-十一烷基咪唑(1’))乙基-均三嗪、2,4-二氨基-6(2’-乙基-4-甲基咪唑(1’))乙基-均三嗪、2,4-二氨基-6(2’-甲基咪唑(1’))乙基-均三嗪·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的各种咪唑类;这些咪唑类与邻苯二甲酸、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、草酸等多元羧酸的盐类。
通过使本发明的树脂组合物固化,从而可以得到显示出良好的导热性的固化物。另外,通过适当选定组成,从而可以赋予涂布性、低粘着性、固化前的涂膜的挠性、固化后的固化物的挠性、与基材的密合性等。因此,使本发明的树脂组合物固化而得到的导热性固化物可以作为印刷布线基板、半导体密封绝缘材料、功率半导体、LED照明、LED背光灯、功率LED、太阳能电池等电气/电子领域的各种构件的树脂基材被广泛应用。更具体而言,作为预浸料、密封剂、层叠基板、涂布性的粘接剂、粘接片等这些固化性成分和各种涂料的固化性成分是有用的。
本发明的导热性固化物为使上述本发明的树脂组合物固化而得到的固化物。导热性固化物的形状没有特别限定,例如可以举出:片状、薄膜状、板状等。片状的固化物可以通过将上述本发明的树脂组合物以膜状涂布于载体膜、金属箔等支撑体上,然后使其固化从而制造。对于本发明的导热性固化物,作为原料的树脂组合物含有有机溶剂的情况下,包含:溶剂残留的状态的固化物和使溶剂挥发而实质上不含溶剂的状态的固化物这两者。
本发明的导热性固化物可以通过应用公知的方法来制造。例如,导热性固化物的形状为片状的情况下,只要使树脂组合物涂覆于支撑体上而形成的涂覆膜固化即可。树脂组合物对支撑体上的涂覆可以使用涂覆装置、喷涂装置。作为涂覆装置,可以举出:辊涂机、棒涂机、刮刀涂布机、凹版涂布机、模涂机、逗点涂布机、帘幕涂布机、丝网印刷装置和毛刷等。
制造片状的导热性固化物时,优选选择容易操作的支撑体来使用。另外,将片状的导热性固化物从支撑体剥离并使用的情况下,优选选择容易剥离导热性固化物的支撑体来使用。作为支撑体,优选载体膜。作为载体膜,例如优选选择由聚对苯二甲酸乙二醇酯、聚对苯二甲酸丁二醇酯等聚酯树脂;氟系树脂、聚酰亚胺树脂等具有耐热性的热塑性树脂形成的薄膜。
另外,使用金属箔作为支撑体的情况下,可以将所形成的导热性固化物从金属箔剥离来使用,或者也可以对金属箔蚀刻不使其剥离来使用。作为金属箔,例如可以优选使用由铜、铜系合金、铝、铝系合金、铁、铁系合金、银、银系合金、金、金系合金、锌、锌系合金、镍、镍系合金、锡、锡系合金等形成的金属箔。另外,作为金属箔,也可以使用带载体箔的极薄金属箔。
本发明的导热性固化物的形状为片状的情况下,片状的导热性固化物的厚度可以根据用途而适当设定,通常为20~150μm的范围。
本发明的导热性固化物显示出良好的导热性,因此可以作为印刷布线基板、半导体密封绝缘材料、功率半导体、LED照明、LED背光灯、功率LED、太阳能电池等电气/电子领域的各种构件的树脂基材被广泛应用。更具体而言,可以用于预浸料、密封剂、层叠基板、涂布性的粘接剂、散热片、粘接片等。
本发明的硅化合物如下述通式(2)所示。本发明的硅化合物特别优选作为负载在用作导热性固化物的制造原料的树脂组合物中配混的导热性填料中的硅烷偶联剂。
(前述通式(2)中,R1分别独立地表示碳原子数1~3的直链或支链状的烷基,A2表示碳原子数1~4的烷二基,X表示下述式(X-1)~(X-6)中的任一者所示的基团,Y表示氢原子、碳原子数1~12的直链或支链状的烷基、碳原子数1~12的直链或支链状的氧基烷基、二甲基氨基、二乙基氨基或乙基甲基氨基)。
通式(2)中的R1、Y和X与前述的通式(1)中的R1、Y和X分别为相同含义。另外,通式(2)中,A2表示碳原子数1~4的烷二基。作为碳原子数1~4的烷二基,可以举出:亚甲基、亚乙基、亚丙基、亚丁基。
通式(2)中的X优选为式(X-1)、式(X-3)、式(X-4)或式(X-6)所示的基团。使用通式(2)中的X为式(X-1)、式(X-3)、式(X-4)或式(X-6)所示基团的硅化合物时,可以大幅提高所得导热性固化物的导热率。另外,通式(2)中的A2为亚丙基的情况下,从经济方面出发为优选。
作为通式(2)所示的硅化合物的优选具体例,可以举出前述化学式No.1~No.54所示的化合物No.1~No.54。需要说明的是,前述通式(2)所示的硅化合物中有时存在偶氮基所引起的2个几何异构体。本发明中,不将它们进行区别,可以为1个几何异构体也可以为2个几何异构体的混合物。
通式(2)所示的硅化合物可以应用公知的反应来制造,对其制造方法没有任何限定。通式(2)所示的硅化合物例如可以如下制造:使与目标化合物对应的结构的羧酸和以3-氨基丙基三烷氧基硅烷为代表的具有氨基的三烷氧基硅烷在碱性下、与以O-(苯并三唑-1-基)-N,N,N’,N’-四甲基脲六氟磷酸酯为代表的缩合剂一起反应从而制造。
本发明的硅化合物可以优选用作导热性填料用的硅烷偶联剂。本发明的硅化合物除了导热性填料用的硅烷偶联剂之外,还可以优选用作光学记录材料、药品、农药、香料、染料等合成中间体;各种功能性材料、各种聚合物原料;光电化学电池、非线形光学装置、电致变色显示器、全息摄影、有机半导体、有机EL;卤化银照片感光材料、光增感剂;印刷油墨、喷墨、电子照片彩色调色剂、化妆品、塑料等中使用的着色剂;蛋白质用染色剂、用于物质检测的发光染料;合成石英原料、涂料、合成催化剂、催化剂载体、表面涂布薄膜材料、硅橡胶交联剂、粘结剂等。
本发明的硅烷偶联剂组合物含有通式(2)所示的本发明的硅化合物,例如可以使其负载于被负载体。对于本发明的硅烷偶联剂组合物,作为除了通式(2)所示的硅化合物以外的成分,还可以进一步含有有机溶剂。
作为使硅烷偶联剂负载于被负载体的方法,可以使用公知的方法。例如,可以使用气层吸附、液层吸附等方法。需要说明的是,作为液层吸附的例子,可以举出如下方法:通过将被负载体浸渍于在溶剂中溶解本发明的硅化合物而得到的溶液,从而使硅化合物吸附于被负载体。
例如,制造在环氧树脂中分散有氮化铝等导热性填料的树脂组合物的情况下,使本发明的硅烷偶联剂组合物负载于该导热性填料时,导热性填料的分散性提高。另外,对于制造在环氧树脂中分散了负载有本发明的硅烷偶联剂组合物的氮化铝填料的树脂组合物,使该树脂组合物固化而得到的导热性固化物,导热性大幅提高。进而,导热性固化物的形状为片状的情况下,可以防止空隙的发生、绝缘击穿电压的降低、断裂伸长率的降低所导致的片的强韧性降低等。
作为本发明的硅烷偶联剂组合物中能够含有的有机溶剂,可以举出:醇系溶剂、二醇系溶剂、酮系溶剂、酯系溶剂、醚系溶剂、脂肪族或脂环族烃系溶剂、芳香族烃系溶剂、具有氰基的烃溶剂、卤代芳香族烃系剂、其他溶剂等。
作为醇系溶剂,可以举出:甲醇、乙醇、丙醇、2-丙醇、1-丁醇、异丁醇、2-丁醇、叔丁醇、戊醇、异戊醇、2-戊醇、新戊醇、叔戊醇、己醇、2-己醇、庚醇、2-庚醇、辛醇、2-乙基己醇、2-辛醇、环戊醇、环己醇、环庚醇、甲基环戊醇、甲基环己醇、甲基环庚醇、苄基醇、乙二醇单甲醚、乙二醇单乙醚、丙二醇单甲醚、丙二醇单乙醚、二乙二醇单甲醚、二乙二醇单乙醚、三乙二醇单甲醚、三乙二醇单乙醚、2-(N,N-二甲基氨基)乙醇、3(N,N-二甲基氨基)丙醇等。
作为二醇系溶剂,可以举出:乙二醇、丙二醇、1,2-丁二醇、1,3-丁二醇、1,4-丁二醇、1,5-戊二醇、新戊二醇、异丙二醇(3-甲基-1,3-丁二醇)、1,2-己二醇、1,6-己二醇、3-甲基-1,5-戊二醇、1,2-辛二醇、辛二醇(2-乙基-1,3-己二醇)、2-丁基-2-乙基-1,3-丙二醇、2,5-二甲基-2,5-己二醇、1,2-环己二醇、1,4-环己二醇、1,4-环己烷二甲醇等。
作为酮系溶剂,可以举出:丙酮、甲乙酮、甲基异丙基酮、甲基丁基酮、甲基异丁基酮、甲基戊基酮、甲基己基酮、乙基丁基酮、二乙基酮、二丙基酮、二异丁基酮、甲基戊基酮、环己酮、甲基环己酮等。
作为酯系溶剂,可以举出:甲酸甲酯、甲酸乙酯、乙酸甲酯、乙酸乙酯、乙酸异丙酯、乙酸丁酯、乙酸异丁酯、乙酸仲丁酯、乙酸叔丁酯、乙酸戊酯、乙酸异戊酯、乙酸叔戊酯、乙酸苯酯、丙酸甲酯、丙酸乙酯、丙酸异丙酯、丙酸丁酯、丙酸异丁酯、丙酸仲丁酯、丙酸叔丁酯、丙酸戊酯、丙酸异戊酯、丙酸叔戊酯、丙酸苯酯、2-乙基己酸甲酯、2-乙基己酸乙酯、2-乙基己酸丙酯、2-乙基己酸异丙酯、2-乙基己酸丁酯、乳酸甲酯、乳酸乙酯、甲氧基丙酸甲酯、乙氧基丙酸甲酯、甲氧基丙酸乙酯、乙氧基丙酸乙酯、乙二醇单甲醚乙酸酯、二乙二醇单甲醚乙酸酯、乙二醇单乙醚乙酸酯、乙二醇单丙醚乙酸酯、乙二醇单异丙基醚乙酸酯、乙二醇单丁基醚乙酸酯、乙二醇单仲丁基醚乙酸酯、乙二醇单异丁基醚乙酸酯、乙二醇单叔丁基醚乙酸酯、丙二醇单甲醚乙酸酯、丙二醇单乙醚乙酸酯、丙二醇单丙醚乙酸酯、丙二醇单异丙基醚乙酸酯、丙二醇单丁基醚乙酸酯、丙二醇单仲丁基醚乙酸酯、丙二醇单异丁基醚乙酸酯、丙二醇单叔丁基醚乙酸酯、丁二醇单甲醚乙酸酯、丁二醇单乙醚乙酸酯、丁二醇单丙醚乙酸酯、丁二醇单丙基醚乙酸酯、丁二醇单丁基醚乙酸酯、丁二醇单仲丁基醚乙酸酯、丁二醇单异丁基醚乙酸酯、丁二醇单叔丁基醚乙酸酯、乙酰乙酸甲酯、乙酰乙酸乙酯、氧代丁酸甲酯、氧代丁酸乙酯、γ-内酯、丙二酸二甲酯、琥珀酸二甲酯、丙二醇二乙酸酯、δ-内酯等。
作为醚系溶剂,可以举出:四氢呋喃、四氢吡喃、吗啉、乙二醇二甲基醚、二乙二醇二甲基醚、二丙二醇二甲基醚、三乙二醇二甲基醚、二丁基醚、二乙基醚、二氧杂环己烷等。
作为脂肪族或脂环族烃系溶剂,可以举出:戊烷、己烷、环己烷、甲基环己烷、二甲基环己烷、乙基环己烷、庚烷、辛烷、萘烷、溶剂石脑油、松节油、D-苧烯、蒎烯、石油溶剂油、商品名“スワゾール#310”(CosmoMatsuyamaOilCo.,Ltd.制造)、商品名“Solvesso#100”(Exxon化学株式会社制造)等。
作为芳香族烃系溶剂,可以举出:苯、甲苯、乙基苯、二甲苯、均三甲苯、二乙基苯、异丙苯、异丁基苯、甲基·异丙基苯、四氢化萘。
作为具有氰基的烃溶剂,可以举出:乙腈、1-氰基丙烷、1-氰基丁烷、1-氰基己烷、氰基环己烷、氰基苯、1,3-二氰基丙烷、1,4-二氰基丁烷、1,6-二氰基己烷、1,4-二氰基环己烷、1,4-二氰基苯等。
作为卤代芳香族烃系溶剂,可以举出:四氯化碳、氯仿、三氯乙烯、二氯甲烷等。
作为其他有机溶剂,可以举出:N-甲基-2-吡咯烷酮、二甲基亚砜、二甲基甲酰胺、苯胺、三乙胺、吡啶。
本发明的负载体用于负载前述本发明的硅烷偶联剂组合物。硅烷偶联剂组合物例如被负载于被负载体等。作为被负载体,例如可以举出:丙烯酸类树脂、氟树脂等有机树脂、碳化硅、氧化钛、氧化铝、氧化镁、氧化锆、氮化铝等金属氧化物、氮化硼、氮化硅、氧化硅、沸石、活性炭等。作为使硅烷偶联剂组合物负载于被负载体的方法,可以使用公知的气层吸附、液层吸附等方法。需要说明的是,作为液层吸附的例子,可以举出如下方法:通过使被负载体浸渍于在溶剂中溶解硅烷偶联剂组合物而得到的溶液,从而使硅烷偶联剂组合物吸附于被负载体。
例如,使硅烷偶联剂组合物负载于作为被负载体的氮化铝填料而得到负载体,使该负载体分散在环氧树脂中而得到树脂组合物。如果使所得树脂组合物固化,则可以制造具有高导热性的导热性固化物。
被负载体的形状没有特别限制,例如可以根据负载体的用途从膜状、粉状、粒状等形状中适当选择。另外,对于被负载体的大小、负载体中含有的硅烷偶联剂组合物的量也没有特别限制,可以根据负载体的用途而适当选择。例如,制造用于得到片状的导热性固化物的树脂组合物的情况下,被负载体的平均粒径为1~100μm时,导热性提高效果高,故优选。需要说明的是,本说明书中的“平均粒径”是指,通过激光衍射/散射法求出的粒度分布的累积值50%下的粒径。
本发明的负载体除了配混于作为用于制造导热性固化物的材料使用的树脂组合物之外,还可以用于光电转换元件、催化剂和调色剂等。
实施例
以下,根据实施例和比较例更详细地说明本发明,但本发明不受这些实施例等的任何限定。
<硅化合物的合成>
[实施例1]化合物No.19的合成
将联苯-4-羧酸(5.0mmol、1.0g、东京化成工业株式会社制造)、O-(苯并三唑-1-基)-N,N,N’,N’-四甲基脲六氟磷酸酯(5.0mmol、1.9g)和二甲基甲酰胺(10.0ml)投入到烧瓶中,在40℃下搅拌0.5小时。之后,加入N,N-二异丙基乙基胺(10.0mmol、1.3g)和3-氨基丙基三乙氧基硅烷(5.0mmol、1.12g),进而搅拌2小时。在反应液中加入水(5ml)和氯仿(5ml),进行油水分液。将所得有机层通过柱色谱法(流动相:己烷/乙酸乙酯=3/1(质量比))进行纯化,从而得到白色的固体1.49g(收率74%)。使用UV-VIS(λmax)和1H-NMR(氘代溶剂:CDCl3)确认了所得固体为化合物No.19。将收率和外观观察结果示于表1。另外,将1H-NMR的结果示于表2。
[实施例2~9]化合物No.1、10、20、24、28、37、43和46的合成
将实施例1中使用的联苯-4-羧酸变更为具有与目标化合物对应的结构的羧酸,除此之外,通过与实施例1同样的方法,合成化合物No.1、10、20、24、28、37、43和46。使用UV-VIS(λmax)和1H-NMR(氘代溶剂:CDCl3)确认了合成的化合物为目标化合物。将收率和外观观察结果示于表1。另外,将1H-NMR的结果示于表2。
[制造例1]化合物No.88的合成
使用具有与目标化合物对应的结构的羧酸化合物和胺化合物,除此之外,通过与实施例1同样的方法合成化合物No.88。使用UV-VIS(λmax)和1H-NMR(氘代溶剂:CDCl3)确认了合成的化合物为目标化合物。将收率和外观观察结果示于表1。另外,将1H-NMR的结果示于表2。
表1
表1
表2
表2
<负载体的制造>
[实施例10]负载体No.1的制造
在100ml的茄型瓶中称量氮化铝填料(TokuyamaCorporation制造、H级、球状、粒径:1μm)10.0g,在其中加入化合物No.1950.0mg和甲苯50ml,进行超声波处理30分钟。之后,通过50℃的真空加热处理,使溶剂蒸发。进而,进行100℃的真空加热处理2小时,使化合物No.19固定化在氮化铝填料的表面,从而得到负载体No.1。
[实施例11~18]负载体No.2~9的制造
将实施例10中使用的化合物No.19分别变更为化合物No.1、10、20、24、28、37、43和46,除此之外,通过与实施例10同样的方法得到负载体No.2~9。
[实施例19~21]负载体No.10~12的制造
将实施例10中使用的氮化铝填料变更为混合填料(氮化铝填料(TokuyamaCorporation制造、H级、球状、粒径:1μm)0.83g、氧化铝填料(电气化学工业株式会社制造、DAW-20、球状、粒径:20μm)5.50g、氧化铝填料(电气化学工业株式会社制造、DAW-03、球状、粒径:3μm)1.38g和氧化铝填料(昭和电工株式会社制造、AL-47-1、粉碎状、粒径:1μm)2.29g),以及将化合物No.19分别变更为化合物No.20、24和43,除此之外,通过与实施例10同样的方法得到负载体No.10~12。
[制造例2]负载体No.13的制造
将实施例10中使用的化合物No.19变更为化合物No.88,除此之外,通过与实施例10同样的方法得到负载体No.13。
[制造例3~5]比较负载体1~3的制造
将实施例10中使用的化合物No.19分别变更为以下所示的式(C-1)~(C-3)所示的比较化合物1~3,除此之外,通过与实施例10同样的方法得到比较负载体1~3。
对于负载体No.1~13和比较负载体1~3,将与使用的填料和硅化合物的对应表示于表3。
表3
表3
负载体 | 填料 | 硅化合物 | |
实施例10 | 负载体No.1 | 氮化铝填料 | 化合物No.19 |
实施例11 | 负载体No.2 | 氮化铝填料 | 化合物No.1 |
实施例12 | 负载体No.3 | 氮化铝填料 | 化合物No.10 |
实施例13 | 负载体No.4 | 氮化铝填料 | 化合物No.20 |
实施例14 | 负载体No.5 | 氮化铝填料 | 化合物No.24 |
实施例15 | 负载体No.6 | 氮化铝填料 | 化合物No.28 |
实施例16 | 负载体No.7 | 氮化铝填料 | 化合物No.37 |
实施例17 | 负载体No.8 | 氮化铝填料 | 化合物No.43 |
实施例18 | 负载体No.9 | 氮化铝填料 | 化合物No.46 |
实施例19 | 负载体No.10 | 混合填料 | 化合物No.20 |
实施例20 | 负载体No.11 | 混合填料 | 化合物No.24 |
实施例21 | 负载体No.12 | 混合填料 | 化合物No.43 |
制造例2 | 负载体No.13 | 氮化铝填料 | 化合物No.88 |
制造例3 | 比较负载体1 | 氮化铝填料 | 比较化合物1 |
制造例4 | 比较负载体2 | 氮化铝填料 | 比较化合物2 |
制造例5 | 比较负载体3 | 氮化铝填料 | 比较化合物3 |
<评价>
[评价例1]固定化量的确认
在负载体No.1中加入甲苯50ml,搅拌30分钟,然后静置30分钟,使固体完全沉降,从而得到分析用样品1。分离回收分析用样品1的上清液1ml,用甲苯稀释至25倍,从而得到分析用样品2。对分析用样品2进行UV-VIS测定,从而算出分析用样品2中的化合物No.19的摩尔浓度。然而,根据下述计算式1,算出固定化于负载体No.1的化合物No.19的固定化量。其结果可知,负载体No.1是在氮化铝填料10g的表面固定化有31.6mg(6.7×10-5mol)的化合物No.19而成的。
计算式1:
S1=S2-(C×25×化合物No.19的分子量×L)
S1:固定化于负载体No.1的化合物No.19的固定化量(g)
S2:制造负载体No.1时使用的化合物No.19的量(g)
L:上清液的总容积(l)
C:分析用样品2中的化合物No.19的摩尔浓度(mol/l)
<树脂组合物的制造>
[实施例22~34]树脂组合物No.1~13的制造
在负载体No.1~13(50g)中加入在甲乙酮10.5g中溶解有联苯芳烷基型环氧树脂(商品名“NC-3000H”、日本化药株式会社制造)7g和联苯芳烷基型酚醛树脂(商品名“MEH-7851H”、明和化成株式会社制造)3.5g的溶液、以及咪唑系固化剂(商品名“2PHZ-PW”、四国化成工业株式会社制造)0.1g,使用三辊磨使其分散,从而得到树脂组合物No.1~13。
[制造例6~10]比较树脂组合物1~5的制造
在50g的(i)氮化铝填料(TokuyamaCorporation制造、H级、球状、粒径:1μm)、(ii)混合填料(氮化铝填料(TokuyamaCorporation制造、H级、球状、粒径:1μm)0.83g、氧化铝填料(电气化学工业株式会社制造、DAW-20、球状、粒径:20μm)5.50g、氧化铝填料(电气化学工业株式会社制造、DAW-03、球状、粒径:3μm)1.38g和氧化铝填料(昭和电工株式会社制造、AL-47-1、粉碎状、粒径:1μm)2.29g)、或(iii)比较负载体1~3中,加入在甲乙酮10.5g中溶解有联苯芳烷基型环氧树脂(商品名“NC-3000H”、日本化药株式会社制造)7g和联苯芳烷基型酚醛树脂(商品名“MEH-7851H”、明和化成株式会社制造)3.5g的溶液、以及咪唑系固化剂(商品名“2PHZ-PW”、四国化成工业株式会社制造)0.1g。然后,使用三辊磨使其分散,从而得到比较树脂组合物1~5。
对于树脂组合物No.1~13和比较树脂组合物1~5,将与使用的负载体的对应表示于表4。
表4
表4
树脂组合物 | 负载体 | |
实施例22 | 树脂组合物No.1 | 负载体No.1 |
实施例23 | 树脂组合物No.2 | 负载体No.2 |
实施例24 | 树脂组合物No.3 | 负载体No.3 |
实施例25 | 树脂组合物No.4 | 负载体No.4 |
实施例26 | 树脂组合物No.5 | 负载体No.5 |
实施例27 | 树脂组合物No.6 | 负载体No.6 |
实施例28 | 树脂组合物No.7 | 负载体No.7 |
实施例29 | 树脂组合物No.8 | 负载体No.8 |
实施例30 | 树脂组合物No.9 | 负载体No.9 |
实施例31 | 树脂组合物No.10 | 负载体No.10 |
实施例32 | 树脂组合物No.11 | 负载体No.11 |
实施例33 | 树脂组合物No.12 | 负载体No.12 |
实施例34 | 树脂组合物No.13 | 负载体No.13 |
制造例6 | 比较树脂组合物1 | 氮化铝填料 |
制造例7 | 比较树脂组合物2 | 混合填料 |
制造例8 | 比较树脂组合物3 | 比较负载体1 |
制造例9 | 比较树脂组合物4 | 比较负载体2 |
制造例10 | 比较树脂组合物5 | 比较负载体3 |
<导热性片的制造>
[实施例35~47]固化物No.1~13的制造
通过棒涂机法,将树脂组合物No.1~13以100μm的厚度涂布于PET薄膜,在100℃下进行10分钟加热,从而使其干燥。进而,在190℃下进行90分钟加热使其固化,然后将PET薄膜剥离,制造片状的导热性固化物即固化物No.1~13。
[制造例11~15]比较固化物1~5的制造
通过棒涂机法,将比较树脂组合物1~5以100μm的厚度涂布于PET薄膜,在100℃下进行10分钟加热,从而使其干燥。进而,在190℃下进行90分钟加热使其固化,然后将PET薄膜剥离,制造片状的导热性固化物即比较固化物1~5。
对于固化物No.1~13和比较固化物1~5,将与使用的树脂组合物的对应表示于表5。
表5
表5
固化物 | 树脂组合物 | |
实施例35 | 固化物No.1 | 树脂组合物No.1 |
实施例36 | 固化物No.2 | 树脂组合物No.2 |
实施例37 | 固化物No.3 | 树脂组合物No.3 |
实施例38 | 固化物No.4 | 树脂组合物No.4 |
实施例39 | 固化物No.5 | 树脂组合物No.5 |
实施例40 | 固化物No.6 | 树脂组合物No.6 |
实施例41 | 固化物No.7 | 树脂组合物No.7 |
实施例42 | 固化物No.8 | 树脂组合物No.8 |
实施例43 | 固化物No.9 | 树脂组合物No.9 |
实施例44 | 固化物No.10 | 树脂组合物No.10 |
实施例45 | 固化物No.11 | 树脂组合物No.11 |
实施例46 | 固化物No.12 | 树脂组合物No.12 |
实施例47 | 固化物No.13 | 树脂组合物No.13 |
制造例11 | 比较固化物1 | 比较树脂组合物1 |
制造例12 | 比较固化物2 | 比较树脂组合物2 |
制造例13 | 比较固化物3 | 比较树脂组合物3 |
制造例14 | 比较固化物4 | 比较树脂组合物4 |
制造例15 | 比较固化物5 | 比较树脂组合物5 |
<评价>
[评价例2]导热性的评价
对于固化物No.1~13和比较固化物1~5,使用热扩散率/导热率测定装置(商品名“Ai-PhaseMobile”、Ai-PhaseCo.,Ltd.制造),通过周期加热法测定热扩散率。将结果示于表6。
表6
表6
固化物 | 热扩散率×10-6(m2/s) | |
评价例2-1 | 固化物No.1 | 1.28 |
评价例2-2 | 固化物No.2 | 1.13 |
评价例2-3 | 固化物No.3 | 1.07 |
评价例2-4 | 固化物No.4 | 1.26 |
评价例2-5 | 固化物No.5 | 1.16 |
评价例2-6 | 固化物No.6 | 1.13 |
评价例2-7 | 固化物No.7 | 1.10 |
评价例2-8 | 固化物No.8 | 1.28 |
评价例2-9 | 固化物No.9 | 1.07 |
评价例2-10 | 固化物No.10 | 1.11 |
评价例2-11 | 固化物No.1 | 1.12 |
评价例2-12 | 固化物No.12 | 1.15 |
评价例2-13 | 固化物No.13 | 1.10 |
比较例1 | 比较固化物1 | 0.93 |
比较例2 | 比较固化物2 | 0.98 |
比较例3 | 比较固化物3 | 0.95 |
比较例4 | 比较固化物4 | 0.99 |
比较例5 | 比较固化物5 | 0.93 |
如表6所示那样,可知,固化物No.1~13的热扩散率与比较固化物1~5的热扩散率相比,提高10~38%左右。其中可知,固化物No.1、4和8显示出特别高的导热性。由以上可知,使用本发明的树脂组合物制造的固化物为具有高导热性的导热性固化物。
Claims (5)
1.一种树脂组合物,其含有:负载有硅烷偶联剂组合物的负载体,
所述硅烷偶联剂组合物含有下述通式(1)所示的硅化合物,
所述通式(1)中,R1分别独立地表示碳原子数1~3的直链或支链状的烷基,A1表示单键或碳原子数1~4的烷二基,Y表示氢原子、碳原子数1~12的直链或支链状的烷基、碳原子数1~12的直链或支链状的氧基烷基、二甲基氨基、二乙基氨基或乙基甲基氨基,X表示下述式(X-1)~(X-6)中的任一者所示的基团,X是下述式(X-1)所示基团的情况下的Z为-NHCO-,X是下述式(X-2)~(X-6)中的任一者所示基团的情况下的Z为单键或-NHCO-,
2.一种导热性固化物,其是使权利要求1所述的树脂组合物固化而得到的。
3.一种下述通式(2)所示的硅化合物,
所述通式(2)中,R1分别独立地表示碳原子数1~3的直链或支链状的烷基,A2表示碳原子数1~4的烷二基,X表示下述式(X-1)~(X-6)中的任一者所示的基团,Y表示氢原子、碳原子数1~12的直链或支链状的烷基、碳原子数1~12的直链或支链状的氧基烷基、二甲基氨基、二乙基氨基或乙基甲基氨基,
4.一种硅烷偶联剂组合物,其含有权利要求3所述的硅化合物。
5.一种负载体,其负载有权利要求4所述的硅烷偶联剂组合物。
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CN113227290A (zh) * | 2018-12-26 | 2021-08-06 | 引能仕株式会社 | 硅烷化合物及其组合物 |
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KR102052198B1 (ko) * | 2016-12-22 | 2019-12-04 | 삼성에스디아이 주식회사 | 고리 연결된 아미드기 및 알콕시 실란기 함유 화합물, 이를 포함하는 에폭시 수지 조성물 및 이를 사용하여 제조된 장치 |
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Also Published As
Publication number | Publication date |
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WO2015083620A1 (ja) | 2015-06-11 |
TW201529664A (zh) | 2015-08-01 |
KR20160094407A (ko) | 2016-08-09 |
JP6224444B2 (ja) | 2017-11-01 |
JP2015105375A (ja) | 2015-06-08 |
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