CN108291012A - 阳离子固化性树脂组合物 - Google Patents
阳离子固化性树脂组合物 Download PDFInfo
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- CN108291012A CN108291012A CN201680070118.9A CN201680070118A CN108291012A CN 108291012 A CN108291012 A CN 108291012A CN 201680070118 A CN201680070118 A CN 201680070118A CN 108291012 A CN108291012 A CN 108291012A
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- cation
- ingredient
- curable resin
- resin composition
- salt
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Abstract
本发明的目的在于提供维持光固化性和低温固化性并且具有储存稳定性的阳离子固化性树脂组合物。具体而言,本发明提供一种含有下述的(A)~(C)成分的阳离子固化性树脂组合物。(A)成分:阳离子聚合性化合物,(B)成分:光阳离子聚合引发剂,(C)成分:含有胺盐的热阳离子聚合引发剂。
Description
技术领域
本发明涉及维持光固化性和低温(例如,小于100℃)固化性并且具有储存稳定性的阳离子固化性树脂组合物。
背景技术
一直以来,含有环氧树脂等的阳离子聚合性树脂组合物由于粘接力、封装性、高强度、耐热性、电特性、耐化学药品性优异,因此,在粘接剂、封装剂、灌封剂、涂层剂、导电性糊料等各种用途中使用。另外,其对象遍及多个领域,特别是在电子设备中,被用于半导体、液晶显示器、有机电致发光、触摸面板等平板显示器、硬盘装置、移动终端装置、相机模块等。
专利文献1公开了含有环氧树脂和通过紫外线等活性能量线的照射而产生路易斯酸的光阳离子引发剂的光阳离子聚合性树脂组合物。另外,专利文献2公开了含有环氧树脂成分、光阳离子引发剂、热阳离子引发剂和填充剂的阳离子固化型环氧树脂组合物。
现有技术文献
专利文献
专利文献1:日本特开昭59-204676号公报
专利文献2:国际公开第2005/059002号小册子
发明内容
然而,专利文献1公开的阳离子聚合性树脂组合物存在不能使未照射光的部位固化的问题。为了解决该问题,也考虑通过加热至200℃左右,由阳离子引发剂产生酸,使其固化,但由于是太高温的固化条件,因此,存在难以应用于容易因热而劣化的液晶、有机EL元件等用途的问题。另外,专利文献2公开的阳离子固化型环氧树脂组合物由于并用光阳离子引发剂和热阳离子引发剂,因此,在室温下几天日内凝胶化等储存稳定性差。
本发明的目的在于解决上述问题点,即,提供维持光固化性和低温固化性并且具有储存稳定性的阳离子固化性树脂组合物。
本发明克服了上述的以往的问题点。即,本发明具有以下主旨。
一种阳离子固化性树脂组合物,含有下述的(A)~(C)成分。
(A)成分:阳离子聚合性化合物
(B)成分:光阳离子聚合引发剂
(C)成分:含有胺盐的热阳离子聚合引发剂
具体而言,本发明可以为以下方式。
〔1〕
一种阳离子固化性树脂组合物,含有下述的(A)~(C)成分。
(A)成分:阳离子聚合性化合物
(B)成分:光阳离子聚合引发剂
(C)成分:含有胺盐的热阳离子聚合引发剂
〔2〕
根据上述〔1〕所述的阳离子固化性树脂组合物,其特征在于,上述(C)成分为含有具有季铵阳离子的盐的热阳离子聚合引发剂。
〔3〕
根据上述〔1〕或〔2〕所述的阳离子固化性树脂组合物,其特征在于,上述(C)成分从由季铵阳离子和硼酸根阴离子构成的盐、由季铵阳离子和锑阴离子构成的盐、由季铵阳离子和磷酸根阴离子构成的盐中选择1种以上。
〔4〕
根据上述〔1〕~〔3〕中任一项所述的阳离子固化性树脂组合物,其特征在于,上述(C)成分从由季铵阳离子和硼酸根阴离子构成的盐、由季铵阳离子和锑阴离子构成的盐中选择1种以上。
〔5〕
根据上述〔1〕~〔4〕中任一项所述的阳离子固化性树脂组合物,其特征在于,上述(A)成分从环氧树脂、氧杂环丁烷化合物和乙烯基醚化合物中选择1种以上。
〔6〕
根据上述〔1〕~〔5〕中任一项所述的阳离子固化性树脂组合物,其特征在于,相对于上述(A)成分100质量份,含有(B)成分0.1~30质量份、(C)成分0.1~30质量份。
〔7〕
根据上述〔1〕~〔6〕中任一项所述的阳离子固化性树脂组合物,其特征在于,上述(B)成分至少含有芳香族碘盐、芳香族锍盐中的任一者。
〔8〕
根据上述〔1〕~〔7〕中任一项所述的阳离子固化性树脂组合物,其特征在于,进一步含有着色剂作为(D)成分。
〔9〕
一种被粘物的粘接方法,具有以下工序,工序1,在一对被粘物之间配置上述〔1〕~〔8〕中任一项所述的阳离子固化性树脂组合物,工序2,对上述阳离子固化性树脂组合物照射活性能量线,以及工序3,在上述照射后在以45℃以上且小于100℃的温度进行加热。
〔10〕
一种固化物,是使上述〔1〕~〔8〕中任一项所述的阳离子固化性树脂组合物固化而成的。
本发明提供维持光固化性和低温(例如,小于100℃)固化性并且具有储存稳定性的阳离子固化性树脂组合物。
具体实施方式
以下对本发明进行详细说明。
<阳离子固化性树脂组合物>
本发明涉及含有下述的(A)~(C)成分和任意含有(D)成分以及添加剂的阳离子固化性树脂组合物。
(A)成分:阳离子聚合性化合物
(B)成分:光阳离子聚合引发剂
(C)成分:含有胺盐的热阳离子聚合引发剂
(D)成分:着色剂
作为本发明的阳离子固化性树脂组合物的各(A)~(D)成分以及添加剂,可以任意地组合使用满足下述的任一条件的物质。
<(A)成分>
作为本发明的(A)成分的阳离子聚合性化合物是利用通过活性能量线的照射或加热而由阳离子聚合引发剂产生的阳离子种引起交联反应的化合物。作为(A)成分,没有特别限定,例如可使用环氧树脂、氧杂环丁烷化合物、乙烯基醚化合物等。其中,从固化物的特性优异的观点考虑,优选环氧树脂。这些化合物可单独使用1种或者将2种以上组合使用。在使用2种作为(A)成分的阳离子聚合性化合物的情况下,例如适当的是以10:1~1:10、优选以5:1~1:5、更优选以3:1~1:3、进一步优选以2:1~1:2、特别优选以1:1的质量比使用该2种(A)成分。
这里,作为活性能量线,例如可举出紫外线、电子束、可见光线等。活性能量线的累计光量例如适当的是300~100000mJ/cm2,优选为500~50000mJ/cm2,更优选为1000~10000mJ/cm2,进一步优选为2000~5000mJ/cm2,特别优选为约3000mJ/cm2。活性能量线的波长优选为150~830nm,更优选为200~600nm,进一步优选为250~380nm。
另外,阳离子聚合性化合物的加热温度例如适当的是45℃以上且小于100℃,更优选为50℃以上且小于95℃,进一步优选为55℃以上且小于90℃、特别优选为80℃±5℃。
上述(A)成分在25℃为液状,由于操作性和低温固化性优异,因此优选。另外,25℃的粘度优选为0.1~30000mPa·s,进一步优选为1~15000mPa·s,更优选为5~10000mPa·s,特别优选为10~1000mPa·s。
作为上述(A)成分的环氧树脂,可举出氢化(加氢)环氧树脂、脂环式环氧树脂、芳香族环氧树脂等,其中,从低温固化性优异的观点考虑,优选氢化环氧树脂、脂环式环氧树脂。应予说明,氢化环氧树脂是指将环氧树脂的芳香环进行核氢化而得到的化合物等。
作为上述氢化环氧树脂,没有特别限定,例如可举出氢化双酚A型环氧树脂、氢化双酚F型环氧树脂、氢化双酚E型环氧树脂、氢化双酚A型的氧化烯加成物的二缩水甘油醚、氢化双酚F的氧化烯加成物的二缩水甘油醚、氢化苯酚酚醛清漆环氧树脂、氢化甲酚酚醛清漆环氧树脂等,特别是从低温固化性优异的方面考虑,优选氢化双酚A型环氧树脂、氢化双酚F型环氧树脂、氢化双酚E型环氧树脂。
作为上述的氢化双酚A型环氧树脂的市售品,例如可举出YX-8000、YX-8034(三菱化学株式会社制造)、EXA-7015(DIC公司制造)、ST-3000(新日铁住金化学株式会社制造)、RIKARESIN HBE-100(新日本理化株式会社)、EX-252(Nagase Chemtex株式会社)等。另外,作为氢化双酚F型环氧树脂的市售品,例如可举出YL-6753(三菱化学株式会社制造)等。
作为上述脂环式环氧树脂,没有特别限定,例如可举出3,4-环氧环己基甲基(3’,4’-环氧)环己烷羧酸酯、ε-己内酯改性3’,4’-环氧环己基甲基3,4-环氧环己烷羧酸酯、双(3,4-环氧环己基)己二酸酯、1,2-环氧-4-乙烯基环己烷、1,4-环己烷二甲醇二缩水甘油醚、环氧乙基二乙烯基环己烷、二环氧乙烯基环己烷、1,2,4-三环氧乙基环己烷、柠檬烯二氧化物、含有脂环式环氧基的有机硅低聚物等。
作为上述脂环式环氧树脂的市售品没有特别限定,例如可举出CELLOXIDE 2081(3’,4’-环氧环己基甲基3,4-环氧环己烷羧酸酯)、CELLOXIDE 2021P(3’,4’-环氧环己基甲基3,4-环氧环己烷羧酸酯)、CELLOXIDE 2000(1,2-环氧-4-乙烯基环己烷)、CELLOXIDE3000(1-甲基-4-(2-甲基环氧乙烷基)-7-氧杂双环[4.1.0]庚烷)、EHPE3150(2,2-双(羟甲基)-1-丁醇的1,2-环氧-4-(2-环氧乙烷基)环己烷加成物)(株式会社Daicel制造)、TTA21(Jiangsu TetraChem公司制造)、X-40-2670、X-22-169AS、X-22-169B(信越化学)等,但并不限定于这些。
作为上述芳香族环氧树脂,可举出芳香族双酚A型环氧树脂、芳香族双酚F型环氧树脂、芳香族双酚E型环氧树脂、芳香族双酚A型的氧化烯加成物的二缩水甘油醚、芳香族双酚F型的氧化烯加成物的二缩水甘油醚、芳香族双酚E型的氧化烯加成物的二缩水甘油醚、芳香族酚醛清漆型环氧树脂、氨酯改性芳香族环氧树脂、含氮芳香族环氧树脂、含有聚丁二烯或丁腈橡胶(NBR)等的橡胶改性芳香族环氧树脂等。
作为上述芳香族环氧树脂的市售品,例如可举出jER825、827、828、828EL、828US、828XA、834、806、806H、807、604、630(三菱化学株式会社制造)、EPICLON830、EXA-830LVP、EXA-850CRP、835LV、HP4032D、703、720、726、HP820、N-660、N-680、N-695、N-655-EXP-S、N-665-EXP-S、N-685-EXP-S、N-740、N-775、N-865(DIC株式会社制造)、EP4100、EP4000、EP4080、EP4085、EP4088、EP4100HF、EP4901HF、EP4000S、EP4000L、EP4003S、EP4010S、EP4010L(株式会社ADEKA制造)、DENACOL EX614B、EX411、EX314、EX201、EX212、EX252(Nagase Chemtex株式会社制造)等,但并不限定于这些。这些市售品可以分别单独使用,另外,也可以混合使用两种以上。
作为上述氧杂环丁烷化合物,例如可举出3-乙基-3-羟甲基氧杂环丁烷、3-(甲基)烯丙氧基甲基-3-乙基氧杂环丁烷、(3-乙基-3-氧杂环丁烷基甲氧基)甲基苯、4-氟-[1-(3-乙基-3-氧杂环丁烷基甲氧基)甲基]苯、[1-(3-乙基-3-氧杂环丁烷基甲氧基)乙基]苯醚、异丁氧基甲基(3-乙基-3-氧杂环丁烷基甲基)醚、2-乙基己基(3-乙基-3-氧杂环丁烷基甲基)醚、乙基二乙二醇(3-乙基-3-氧杂环丁烷基甲基)醚、四氢糠基(3-乙基-3-氧杂环丁烷基甲基)醚、四溴苯基(3-乙基-3-氧杂环丁烷基甲基)醚、2-四溴苯氧基乙基(3-乙基-3-氧杂环丁烷基甲基)醚、五氯苯基(3-乙基-3-氧杂环丁烷基甲基)醚、五溴苯基(3-乙基-3-氧杂环丁烷基甲基)醚、乙二醇双(3-乙基-3-氧杂环丁烷基甲基)醚、三乙二醇双(3-乙基-3-氧杂环丁烷基甲基)醚、四乙二醇双(3-乙基-3-氧杂环丁烷基甲基)醚、三羟甲基丙烷三(3-乙基-3-氧杂环丁烷基甲基)醚、季戊四醇三(3-乙基-3-氧杂环丁烷基甲基)醚、季戊四醇四(3-乙基-3-氧杂环丁烷基甲基)醚、二季戊四醇四(3-乙基-3-氧杂环丁烷基甲基)醚、二(三羟甲基)丙烷四(3-乙基-3-氧杂环丁烷基甲基)醚等。作为上述氧杂环丁烷化合物的市售品,例如可举出OXT-212、OXT-221,OXT-213、OXT-101(东亚合成株式会社制造)等。
作为上述乙烯基醚化合物,例如可举出1,4-丁二醇二乙烯基醚、二乙二醇二乙烯基醚、三乙二醇二乙烯基醚、四乙二醇二乙烯基醚、正丙基乙烯基醚、异丙基乙烯基醚、正丁基乙烯基醚、异丁基乙烯基醚、2-乙基己基乙烯基醚、环己基乙烯基醚、2-羟基乙基乙烯基醚,二乙二醇单乙烯基醚、4-羟丁基乙烯基醚、丙烯酸2-(2-乙烯氧基乙氧基)乙酯、甲基丙烯酸2-(2-乙烯氧基乙氧基)乙酯等。可举出NPVE、IPVE、NBVE、IBVE、EHVECHVE(日本Carbide工业株式会社制造)、HEVE、DEGV、HBVE(丸善石油化学株式会社)、VEEA、VEEM(株式会社日本催化剂制造)等。
<(B)成分>
本发明的(B)成分为光阳离子聚合引发剂,是通过活性能量线的照射而产生阳离子种的化合物。作为(B)成分,没有特别限定,例如可举出芳香族碘盐、芳香族锍盐等盐。这些引发剂可以单独使用,也可以并用2种以上。上述芳香族锍系光阳离子聚合引发剂可举出含有与硫原子键合的3个基团均为芳基的锍离子的光阳离子聚合引发剂等。另外,上述芳香族碘系光阳离子聚合引发剂可举出含有与碘原子键合的2个基团为芳基的碘离子的光阳离子聚合引发剂等。在使用2种作为(B)成分的光阳离子聚合引发剂的情况下,例如适当的是以10:1~1:10、优选以5:1~1:5、更优选以3:1~1:3、进一步优选以2:1~1:2、特别优选以1:1的质量比使用该2种(B)成分。
这里,优选的活性能量线的种类、优选的活性能量线的累计光量、优选的活性能量线的波长如在上述(A)成分的说明中记载所示。
作为上述芳香族碘盐,例如可举出二苯基碘四(五氟苯基)硼酸盐、二苯基碘六氟磷酸盐、二苯基碘六氟锑酸盐、二(4-壬基苯基)碘六氟磷酸盐、4-甲基苯基-4-(1-甲基乙基)苯基碘四(五氟苯基)硼酸盐等。
作为上述芳香族碘盐的市售品,可举出IRGACURE 250(BASF公司制造)、PI-2074(Rhodia公司制造、4-甲基苯基-4-(1-甲基乙基)苯基碘-四(五氟苯基)硼酸盐)、B2380(双(4-叔丁基苯基)碘六氟磷酸盐)、B2381、D2238、D2248、D2253、I0591(东京化成工业株式会社制造)、WPI-113(双[4-正烷基(C10~13)苯基]碘·六氟磷酸盐)、WPI-116(双[正烷基(C10~13)苯基]碘·六氟锑酸盐)、WPI-169、WPI-170(双(4-叔丁基苯基)碘·六氟磷酸盐)、WPI-124(双[4-正烷基(C10~13)苯基]碘·四氟苯基硼酸盐)(和光纯药工业株式会社制造)等。
作为上述芳香族锍盐,例如可举出三苯基锍六氟磷酸盐、三苯基锍六氟锑酸盐、三苯基锍四(五氟苯基)硼酸盐、4,4’-双〔二苯基锍基〕二苯硫醚-双六氟磷酸盐、4,4’-双〔二(β-羟基乙氧基)苯基锍基〕二苯硫醚-双六氟锑酸盐、4,4’-双〔二(β-羟基乙氧基)苯基锍基〕二苯硫醚-双六氟磷酸盐、7-〔二(对甲苯酰基)锍基〕-2-异丙基噻吨酮六氟锑酸盐、7-〔二(对甲苯酰基)锍基〕-2-异丙基噻吨酮四(五氟苯基)硼酸盐、4-苯基羰基-4’-二苯基锍基-二苯硫醚-六氟磷酸盐、4-(对叔丁基苯基羰基)-4’-二苯基锍基-二苯硫醚-六氟锑酸盐、4-(对叔丁基苯基羰基)-4’-二(对甲苯酰基)锍基-二苯硫醚-四(五氟苯基)硼酸盐等。不限定于这些芳香族锍盐。这些光阳离子聚合引发剂可以单独或者混合使用。
作为芳香族锍盐的市售品,可举出SP-150、SP-170、SP-172(株式会社ADEKA公司制造)、CPI-100P、CPI-101A、CPI-110B、CPI-200K、CPI-210S(San-Apro株式会社制造)、T1608、T1609、T2041(三(4-甲基苯基)锍六氟磷酸盐)、T2042(三-对甲苯基锍三氟甲烷磺酸盐)(东京化成工业株式会社制造)、UVI-6990、UVI-6974(Union Carbide公司制造)、DTS-200(Midori化学公司制造)等。
本发明的阳离子固化性树脂组合物中的(B)成分的配合量没有特别限制,相对于上述(A)成分100质量份,优选为0.1~30质量份的范围内,更优选为0.5~15质量份。如果为0.1质量份以上,则可得到充分的光固化性,另外,如果为30质量份以下,则能够充分溶解于上述(A)成分,因此优选。
对活性能量线和热这两者具有活性的阳离子聚合引发剂(其中,不包括(C)成分)在本发明中作为(B)成分处理。
<(C)成分>
作为本发明的(C)成分,是含有胺盐的热阳离子聚合引发剂,是通过加热而产生阳离子种的化合物。作为(C)成分,例如可举出含有具有季铵阳离子的盐的热阳离子聚合引发剂等。作为更具体的(C)成分,可举出由季铵阳离子和硼酸根阴离子构成的盐、由季铵阳离子和锑阴离子构成的盐、由季铵阳离子和磷酸根阴离子构成的盐等,其中,从低温固化性优异的方面考虑,优选由季铵阳离子和硼酸根阴离子构成的盐、由季铵阳离子和锑阴离子构成的盐。
作为上述硼酸根阴离子,可举出四氟硼酸根阴离子、四(全氟苯基)硼酸根阴离子等。作为上述锑阴离子,可举出四氟锑阴离子、四(全氟苯基)锑阴离子等。作为上述磷酸根阴离子,可举出六氟磷酸根阴离子、三氟[三(全氟乙基)]等。
作为(C)成分的市售品,例如可举出CXC-1612(King Industries公司制造,含有由季铵阳离子和硼酸根阴离子构成的盐的热阳离子聚合引发剂)、CXC-1821(KingIndustries公司制造,含有由季铵阳离子和锑阴离子构成的盐的热阳离子聚合引发剂)等。
本发明的阳离子固化性树脂组合物中的(C)成分的配合量没有特别限制,相对于上述(A)成分100质量份,优选为0.1~30质量份的范围内,更优选为0.5~15质量份。如果为0.1质量份以上,则可得到充分的低温固化性,另外,如果为30质量份以下,则储存稳定性也不会降低,因此优选。
这里,(B)成分与(C)成分的配合比以(B)成分:(C)成分的质量比计例如适当的是10∶1~1∶10,优选为5∶1~1∶5,更优选为3∶1~1∶3,进一步优选为3∶1~3∶2。
<(D)成分>
进而,可以在不损害本发明的特性的范围内使本发明的阳离子固化性树脂组合物含有作为(D)成分的颜料、染料等着色剂。其中,从耐久性的观点考虑,优选颜料。颜料中,从隐蔽性优异的观点考虑,优选黑色颜料。作为黑色颜料,例如可举出炭黑、黑色氧化钛、铜铬黑、花青黑、苯胺黑等,其中,从隐蔽性和相对于本发明的(A)成分的分散性的观点考虑,优选炭黑。
本发明的阳离子固化性树脂组合物中的(D)成分的配合量没有特别限制,适当的是相对于上述(A)成分100质量份,优选为0.01~30质量份的范围内,更优选为0.05~10质量份,进一步优选为0.1~5质量份。
<添加剂>
进而,本发明的阳离子固化性树脂组合物可以在不损害本发明的特性的范围内适量配合敏化剂、硅烷偶联剂、多元醇化合物、过氧化物、硫醇化合物、保存稳定剂等添加剂。另外,本发明的阳离子固化性树脂组合物可以在不损害本发明的特性的范围内适量配合碳酸钙、碳酸镁、氧化钛、氢氧化镁、滑石、二氧化硅、氧化铝、玻璃、氢氧化铝、氮化硼、氮化铝和氧化镁等平均粒径为0.001~100μm的无机填充剂;银等导电性粒子;阻燃剂;丙烯酸橡胶、硅橡胶等橡胶;增塑剂;有机溶剂这样的溶剂;酚系抗氧化剂、磷系抗氧化剂等系抗氧化剂;光稳定剂;紫外线吸收剂;消泡剂;发泡剂;脱模剂;流平剂;流变控制剂;增粘剂;固化延迟剂;聚酰亚胺树脂、聚酰胺树脂、苯氧基树脂类、氰酸酯类、聚(甲基)丙烯酸酯树脂类、聚氨酯树脂类、聚脲树脂、聚酯树脂类、聚乙烯醇缩丁醛树脂、SBS、SEBS等聚合物、热塑性弹性体等各种添加剂。通过这些添加剂的添加,可得到树脂强度·粘接强度·阻燃性·热传导性、操作性等更优异的阳离子固化性树脂组合物和其固化物。
作为上述敏化剂,可举出9-芴酮、蒽酮、二苯并环庚酮、芴、2-溴芴、9-溴芴、9,9-二甲基芴、2-氟芴、2-碘芴、2-芴胺、9-芴醇、2,7-二溴芴、9-氨基芴盐酸盐、2,7-二氨基芴、9,9’-螺双[9H-芴]、2-芴甲醛、9-芴基甲醇、2-乙酰基芴、二苯甲酮、二乙氧基苯乙酮、2-羟基-2-甲基-1-苯基丙烷-1-酮、苄基二甲基缩酮、4-(2-羟基乙氧基)苯基-(2-羟基-2-丙基)酮、1-羟基-环己基-苯基-酮、2-甲基-2-吗啉基(4-硫代甲基苯基)丙烷-1-酮、2-苄基-2-二甲基氨基-1-(4-吗啉基苯基)丁酮、2-羟基-2-甲基-1-[4-(1-甲基乙烯基)苯基]丙酮低聚物、硝基化合物、色素等。添加量没有特别限定,需要将吸收波长和摩尔消光系数作为参考。
作为上述硅烷偶联剂,例如可举出3-环氧丙氧基丙基三乙氧基硅烷、3-环氧丙氧基丙基甲基二甲氧基硅烷、3-环氧丙氧基丙基三甲氧基硅烷、3-环氧丙氧基丙基甲基二乙氧基硅烷等含有缩水甘油基的硅烷偶联剂、乙烯基三(β-甲氧基乙氧基)硅烷、乙烯基三乙氧基硅烷、乙烯基三甲氧基硅烷等含有乙烯基的硅烷偶联剂、γ-甲基丙烯酰氧基丙基三甲氧基硅烷等含有(甲基)丙烯酰基的硅烷偶联剂、N-β-(氨基乙基)-γ-氨基丙基三甲氧基硅烷、γ-氨基丙基三乙氧基硅烷、N-苯基-γ-氨基丙基三甲氧基硅烷等含有氨基的硅烷偶联剂以及γ-巯基丙基三甲氧基硅烷、γ-氯丙基三甲氧基硅烷等。这些硅烷偶联剂中,优选使用含有缩水甘油基的硅烷偶联剂,含有缩水甘油基的硅烷偶联剂中,优选3-环氧丙氧基丙基三甲氧基硅烷、3-环氧丙氧基丙基三乙氧基硅烷。这些硅烷偶联剂可以单独使用,也可以并用2种以上。
作为上述多元醇化合物,可以为了调整固化速度、进一步提高粘接力而添加。作为上述多元醇化合物,例如可举出乙二醇、丙二醇、1,4-丁二醇、1,3-丁二醇、1,9-壬二醇、新戊二醇、三环癸烷二甲醇、环己烷二甲醇、三羟甲基丙烷、甘油、氢化聚丁二烯多元醇、氢化二聚体二醇等脂肪族多元醇、二乙二醇、三丙二醇、聚乙二醇、聚丙二醇、聚丁二醇、三羟甲基丙烷聚乙氧基三醇、甘油聚丙氧基三醇、双酚A聚乙氧基二醇、双酚F聚乙氧基二醇、二(三羟甲基)丙烷等具有1个或2个以上醚键的(聚)醚多元醇、聚酯多元醇化合物、聚己内酯多元醇化合物、具有酚性羟基的多元醇化合物、聚碳酸酯二醇等聚碳酸酯多元醇等。
<阳离子固化性树脂组合物的固化>
本发明的阳离子固化性树脂组合物可以通过活性能量线的照射而固化(光固化性)。另外,本发明的阳离子固化性树脂组合物可以通过低温而固化(低温固化性)。进而,本发明的阳离子固化性树脂组合物可以通过活性能量线的照射和低温而固化。
这里,如上述(A)成分的说明所示,作为活性能量线,例如可举出紫外线、电子束、可见光线等。活性能量线的累计光量例如适当的是300~100000mJ/cm2,优选为500~50000mJ/cm2,更优选为1000~10000mJ/cm2,进一步优选为2000~5000mJ/cm2,特别优选为约3000mJ/cm2。活性能量线的波长优选为150~830nm,更优选为200~600nm,更优选为250~380nm。
另外,上述“低温”是指本发明的阳离子固化性树脂组合物的可固化温度低,实际上相当于本发明的阳离子固化性树脂组合物的固化方法的加热条件。该加热条件(可固化温度)没有特别限定,例如适当的是优选为45℃以上且小于100℃的温度,更优选为50℃以上且小于95℃,进一步优选为55℃以上且小于90℃的温度,特别优选为80℃±5℃。另外,可以通过活性能量线的照射而使其固化。作为此时的活性能量线,可举出紫外线、电子束、可见光线等,没有特别限制。活性能量线的累计光量例如适当的是300~100000mJ/cm2,优选为500~50000mJ/cm2,更优选为1000~10000mJ/cm2,进一步优选为2000~5000mJ/cm2,特别优选为约3000mJ/cm2。活性能量线的波长优选为150~830nm,更优选为200~400nm,进一步优选为250~350nm。
<粘接方法>
本发明的阳离子固化性树脂组合物可以进一步用于被粘物的粘接。作为具体的粘接方法,例如可举出被粘物的粘接方法,该方法具有以下工序:工序1,在一对被粘物之间配置本发明的阳离子固化性树脂组合物,工序2,对上述阳离子固化性树脂组合物照射活性能量线,以及工序3,在上述照射后以45℃以上且小于100℃的温度进行加热。以下对各工序进行说明。
[工序1]
在一对被粘物之间配置本发明的阳离子固化性树脂组合物。具体而言,例如,在一个被粘物滴加或涂布阳离子固化性树脂组合物等而配置,在该配置的阳离子固化性树脂组合物上配置另一个被粘物,任意地将一对被粘物的位置对准而定位。上述涂布例如可以使用公知的密封剂、粘接剂的涂布方法。例如可以使用利用自动涂布机的点胶(dispensing)、喷涂、喷墨、丝网印刷、凹版印刷、浸渍、旋涂等方法。作为被粘物,例如可以使用玻璃、塑料等,优选为透明或半透明且具有透光性的平板材料。
[工序2]
对上述配置的阳离子固化性树脂组合物照射活性能量线,进行阳离子固化性树脂组合物的固化,将一对被粘物暂时粘接。基于活性能量线的照射的阳离子固化性树脂组合物的固化特别是在该组合物表面和其附近进行。照射可以对上述配置的阳离子固化性树脂组合物直接进行,特别是在上述被粘物为透明或半透明的情况下,可以介由被粘物而间接地进行。优选的活性能量线的种类、优选的活性能量线的累计光量、优选的活性能量线的波长如上述(A)成分的说明中记载所示。
[工序3]
上述活性能量线的照射后,上述配置的阳离子固化性树脂组合物进一步以规定温度进行加热,阳离子固化性树脂组合物完全固化,一对被粘物被完全粘接(正式粘接)。基于加热的阳离子固化性树脂组合物的固化特别在该组合物表面和其附近以外的该组合物的内部进行。通过在工序3的基于加热的固化反应之前进行上述工序2的基于照射的固化反应,迅速地开始树脂组合物的固化(交联)反应,然后,通过接下来的工序3的基于加热的固化反应,未照射活性能量线的树脂组合物的内部的反应迅速地进行,能够实现树脂组合物的完全固化。
该加热温度例如适当的是45℃~100℃,优选为45℃以上且小于100℃,更优选为50℃以上且小于95℃,进一步优选为55℃以上且小于90℃,特别优选为80℃±5℃。
<阳离子固化性树脂组合物的用途>
作为本发明的阳离子固化性树脂组合物的用途,可举出粘接剂、封装剂、灌封剂、涂层剂、导电糊料、片状粘接剂等。另外,作为粘接剂、密封剂、灌封剂、涂层剂、导电糊料、片状粘合剂的具体的用途,可举出开关部分、车头灯、发动机内部件、电气部件、驱动引擎、制动油箱等汽车领域;液晶显示器、有机电致发光、触摸面板、等离子显示器、发光二极管显示装置等平板显示器领域;视频光盘、CD、DVD、MD、摄像镜头、硬盘周边构件、蓝光光盘等记录领域;电子部件、电路、继电器、电触点或半导体元件等的封装材料、芯片接合剂、导电性粘接剂、各向异性导电性粘接剂、包含堆积基板的多层基板的层间粘接剂等电子材料领域;CMOS图像传感器等相机模块;Li电池、锰电池、碱性电池、镍系电池、燃料电池、硅系太阳能电池、色素敏化型太阳能电池、有机太阳能电池等电池领域;光通信系统中的光开关周边、光连接器周边的光纤材料、光无源部件、光电路部件、光电集成电路周边等光部件领域;移动终端装置;建筑领域;航空领域等。作为特别优选的用途,可举出CMOS图像传感器、框体与镜头等的组装用粘接剂、以防止背光源的漏光、防止外部光的进入等为目的的液晶显示器的密封剂等。
实施例
以下通过实施例对本发明具体地进行说明,但本发明不受以下的实施例限制。
<阳离子固化性树脂组合物的制备>
·实施例1
添加作为(A)成分的在25℃粘度为1900mPa·s的氢化双酚A型环氧树脂(a1)(YX-8000,三菱化学株式会社制造)100质量份、作为(B)成分的4-甲基苯基-4-(1-甲基乙基)苯基碘-四(五氟苯基)硼酸盐(b1)(PI-2074,Rhodia公司制造)3质量份、作为(C)成分的含有由季铵阳离子和硼酸根阴离子构成的盐的热阳离子聚合引发剂(c1)(CXC-1821,KingIndustries公司制造)1质量份,在遮光下在常温(25℃)利用行星式混合机混合60分钟,得到阳离子固化性树脂组合物即实施例1。
·实施例2
实施例1中,将c1成分1质量份变更为2质量份,除此以外,与实施例1同样地制备,得到实施例2。
·实施例3
实施例1中,代替a1成分,变更为在25℃粘度为300mPa·s的3',4'-环氧环己基甲基3,4-环氧环己烷羧酸酯(a2)(CELLOXIDE 2021P),除此以外,与实施例1同样地制备,得到实施例3。
·实施例4
实施例3中,将c1成分1质量份变更为2质量份,除此以外,与实施例1同样地制备,得到实施例4。
·实施例5
实施例1中,将a1成分100质量份变更为50质量份,进一步以含有a2成分50质量份的方式进行变更,除此以外,与实施例1同样地制备,得到实施例5。
·实施例6
实施例1中,代替c1成分,变更为含有由季铵阳离子和锑阴离子构成的盐的热阳离子聚合引发剂(c2)(CXC-1612,King Industries公司制造),除此以外,与实施例1同样地制备,得到实施例6。
·比较例1
实施例1中,代替c1成分,变更为含有由芳香族锍阳离子和硼酸根阴离子构成的盐的热阳离子聚合引发剂(c’1)(SI-B2A,三新化学工业株式会社制造),除此以外,与实施例1同样地制备,得到比较例1。
·比较例2
实施例1中,代替c1成分,变更为含有由芳香族锍阳离子和磷酸根阴离子构成的盐的热阳离子聚合引发剂(c’2)(SI-110L,三新化学工业株式会社制造),除此以外,与实施例1同样地制备,得到比较例2。
·比较例3
实施例1中,代替c1成分,变更为含有由芳香族锍阳离子和锑阴离子构成的盐的热阳离子聚合引发剂(c’3)(SI-80L,三新化学工业株式会社制造),除此以外,与实施例1同样地制备,得到比较例3。
·比较例4
实施例1中,不包括c1成分,除此以外,与实施例1同样地制备,得到比较例4。
·比较例5
实施例1中,不包括b1成分,除此以外,与实施例1同样地制备,得到比较例5。
<储存稳定性>
将各实施例和比较例制备的阳离子固化性树脂组合物放入容量15ml的塑料容器,在温度25℃的环境下静置30天,然后,利用前端尖的棒接触,基于下述评价标准进行评价。
[评价标准]
OK:未确认到凝胶化,确认为液状。
NG:确认到凝胶化。
<光固化性试验>
在作为一个被粘物的载玻片上滴加·涂布各实施例和比较例中制备的阳离子固化性树脂组合物0.01g,覆盖作为另一个被粘物的盖玻片而制作阳离子固化性组合物以薄膜的方式夹持于一对玻璃片的试验片。接着,利用紫外线照射机(Jatech株式会社制造,型号:JUL-M-433AN-05,紫外线波长:365nm)照射累计光量为3000mJ/cm2的活性能量线后,进行确认一对玻璃片彼此粘接并用手不能移动的试验。
<低温固化性试验>
在设定为80℃的加热板上滴加各实施例和比较例中制备的阳离子固化性树脂组合物0.1g,30分钟后利用前端尖的棒接触,评价组合物有无固化。
[表1]
储存稳定性 | 光固化性试验 | 低温固化性试验 | |
实施例1 | OK | 固化 | 固化 |
实施例2 | OK | 固化 | 固化 |
实施例3 | OK | 固化 | 固化 |
实施例4 | OK | 固化 | 固化 |
实施例5 | OK | 固化 | 固化 |
实施例6 | OK | 固化 | 固化 |
比较例1 | NG | 固化 | 固化 |
比较例2 | NG | 固化 | 未固化 |
比较例3 | OK | 未固化 | 固化 |
比较例4 | OK | 固化 | 未固化 |
比较例5 | OK | 未固化 | 固化 |
根据实施例1~6,可知本发明维持光固化性和低温(小于100℃)固化性并且储存稳定性优异。
比较例1为使用含有不是本发明的(C)成分的由芳香族锍阳离子和硼酸根阴离子构成的盐的热阳离子聚合引发剂的组合物,可知储存稳定性差。另外,比较例2为使用含有不是本发明的(C)成分的由芳香族锍阳离子和磷酸根阴离子构成的盐的热阳离子聚合引发剂的组合物,可知储存稳定性和低温固化性差。另外,比较例3为使用含有不是本发明的(C)成分的由芳香族锍阳离子和锑阴离子构成的盐的热阳离子聚合引发剂的组合物,可知光固化性差。另外,比较例4为不包括本发明的(C)成分的组合物,可知低温固化性差。另外,比较例5为不包括本发明的(B)成分的组合物,可知光固化性差。
接下来,进行评价本发明的阳离子固化性树脂组合物的隐蔽性的试验。
·实施例7
实施例1中,进一步加入作为黑色颜料的炭黑(SRB BLACK T-04,御国色素株式会社制造)1质量份作为(D)成分,除此以外,与实施例1同样地制备,得到实施例7。
<隐蔽性试验>
将实施例7的阳离子固化性树脂组合物以厚度成为0.2mm的方式拉伸而制作表面平滑的试验片,利用紫外线照射机(Jatech株式会社制造,型号:JUL-M-433AN-05,紫外线波长:365nm)照射累计光量3000mJ/cm2的光活性能量。然后,进一步将上述试验片在80℃的恒温槽中加热30分钟,得到固化物。然后,利用光谱光度计UV-2450(岛津制作所制造)测定固化物的550nm波长的绿色光的透射率。透射率小于1%,可以确认固化物的隐蔽性优异。
产业上的可利用性
本发明的阳离子固化性树脂组合物由于维持光固化性和低温(小于100℃)固化性并且储存稳定性优异,因此,可以应用于粘接剂、封装剂、灌封剂、涂层剂、导电糊料、片状粘合剂等广泛的领域,所以在产业上是有用的。
Claims (10)
1.一种阳离子固化性树脂组合物,含有下述的(A)~(C)成分,
(A)成分:阳离子聚合性化合物,
(B)成分:光阳离子聚合引发剂,
(C)成分:含有胺盐的热阳离子聚合引发剂。
2.根据权利要求1所述的阳离子固化性树脂组合物,其特征在于,所述(C)成分为含有具有季铵阳离子的盐的热阳离子聚合引发剂。
3.根据权利要求1或2所述的阳离子固化性树脂组合物,其特征在于,所述(C)成分从由季铵阳离子和硼酸根阴离子构成的盐、由季铵阳离子和锑阴离子构成的盐、由季铵阳离子和磷酸根阴离子构成的盐中选择1种以上。
4.根据权利要求1~3中任一项所述的阳离子固化性树脂组合物,其特征在于,所述(C)成分从由季铵阳离子和硼酸根阴离子构成的盐、由季铵阳离子和锑阴离子构成的盐中选择1种以上。
5.根据权利要求1~4中任一项所述的阳离子固化性树脂组合物,其特征在于,所述(A)成分从环氧树脂、氧杂环丁烷化合物和乙烯基醚化合物中选择1种以上。
6.根据权利要求1~5中任一项所述的阳离子固化性树脂组合物,其特征在于,相对于所述(A)成分100质量份,含有(B)成分0.1~30质量份、(C)成分0.1~30质量份。
7.根据权利要求1~6中任一项所述的阳离子固化性树脂组合物,其特征在于,所述(B)成分至少含有芳香族碘盐、芳香族锍盐中的任一者。
8.根据权利要求1~7中任一项所述的阳离子固化性树脂组合物,其特征在于,进一步含有着色剂作为(D)成分。
9.一种被粘物的粘接方法,其特征在于,具有以下工序:
工序1,在一对被粘物之间配置权利要求1~8中任一项所述的阳离子固化性树脂组合物,
工序2,对所述阳离子固化性树脂组合物照射活性能量线,以及
工序3,在所述照射后以45℃以上且小于100℃的温度进行加热。
10.一种固化物,是使权利要求1~8中任一项所述的阳离子固化性树脂组合物固化而成的。
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CN114761460A (zh) * | 2019-12-11 | 2022-07-15 | 三键有限公司 | 阳离子固化性组合物、固化物及接合体 |
CN115836100A (zh) * | 2020-10-30 | 2023-03-21 | 株式会社艾迪科 | 聚合性组合物、固化物及固化物的制造方法 |
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JP6547110B1 (ja) * | 2018-05-08 | 2019-07-24 | ナトコ株式会社 | 活性エネルギー線硬化性インク組成物 |
US20220186066A1 (en) * | 2019-03-26 | 2022-06-16 | Mitsui Chemicals, Inc. | Protection member for semiconductor, protection composition for inkjet coating-type semiconductor, and method for producing semiconductor apparatus using same, and semiconductor apparatus |
JP2022185716A (ja) * | 2021-06-03 | 2022-12-15 | デクセリアルズ株式会社 | 接着剤組成物、接着フィルム、接続構造体および接続構造体の製造方法 |
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