CN116406392A - 固化性组合物、固化物和粘接剂 - Google Patents
固化性组合物、固化物和粘接剂 Download PDFInfo
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- CN116406392A CN116406392A CN202180076359.5A CN202180076359A CN116406392A CN 116406392 A CN116406392 A CN 116406392A CN 202180076359 A CN202180076359 A CN 202180076359A CN 116406392 A CN116406392 A CN 116406392A
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- epoxy resin
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Classifications
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- C08G18/4825—Polyethers containing two hydroxy groups
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Abstract
本发明提供固化性组合物、其固化物和粘接剂,所述固化性组合物的特征在于,其含有封端异氰酸酯预聚物(A)、环氧树脂(B)和固化剂(C),所述封端异氰酸酯预聚物(A)以多元醇化合物(a1)、多异氰酸酯化合物(a2)、封端化剂(a3)作为必须原料,前述封端化剂(a3)包含具有碳原子数为12个以上的烃基的酚化合物。该固化性组合物具有优异的粘接性和耐湿热性,可适合地用于粘接剂等。
Description
技术领域
本发明涉及固化性组合物、固化物和粘接剂。
背景技术
近年来,从节约能源的观点出发,作为结构体材料,推进采用铝、镁、塑料等轻量材料,另外,组装中,利用粘接剂来代替基于焊接的接合的情况也逐渐增加。对汽车等的结构体用粘接剂,要求不同原材料间的粘接性良好、能耐受使用环境的温度/湿度的变化等。为了满足这些要求,例如,从通过改善对基材的追随性从而可以维持粘接性的观点出发,提供了一种组合使用双酚型环氧树脂与氨基甲酸酯改性环氧树脂、橡胶改性环氧树脂而成的粘接剂(例如参照专利文献1)。然而,通过对环氧树脂进行改性从而导入柔软性骨架的情况下,其导入量存在上限,有时无法充分满足高度化的要求。进而,从耐湿热性的观点来看,由于固化物(粘接层)的疏水性,存在因水分进入基材与固化物的界面而容易发生界面剥离的问题。
因而,寻求具有优异的粘接性和耐湿热性的材料。
现有技术文献
专利文献
专利文献1:日本特开2010-185034号公报
发明内容
发明要解决的问题
本发明要解决的问题在于,提供能够形成具有优异粘接性和耐湿热性的固化物的固化性组合物、前述固化性组合物的固化物和粘接剂。
用于解决问题的方案
本发明人等为了解决上述课题而进行了深入研究,结果发现:通过使用含有封端异氰酸酯预聚物、环氧树脂和固化剂且所述封端异氰酸酯预聚物以多元醇化合物、多异氰酸酯化合物和特定封端化剂作为必须原料的固化性组合物,从而能够解决上述课题,由此完成了本发明。
即,本发明涉及固化性组合物、固化物和粘接剂,所述固化性组合物的特征在于,其含有封端异氰酸酯预聚物(A)、环氧树脂(B)和固化剂(C),所述封端异氰酸酯预聚物(A)以多元醇化合物(a1)、多异氰酸酯化合物(a2)、封端化剂(a3)作为必须原料,前述封端化剂(a3)包含具有碳原子数为12个以上的烃基的酚化合物。
发明的效果
本发明的固化性组合物能够形成具有优异粘接性和耐湿热性的固化物,因此可用作涂布剂、粘接剂,可特别适合地用作粘接剂。
具体实施方式
本发明的固化性组合物的特征在于,其含有封端异氰酸酯预聚物(A)、环氧树脂(B)和固化剂(C)。
作为前述封端异氰酸酯预聚物(A),以多元醇化合物(a1)、多异氰酸酯化合物(a2)和封端化剂(a3)作为必须原料。
作为前述多元醇化合物(a1),可列举出例如聚乙二醇、聚丙二醇、聚四亚甲基二醇等聚醚多元醇;聚酯多元醇、聚碳酸酯多元醇、丙烯酸类多元醇等。这些之中,从可获得能够形成具有优异粘接性和耐湿热性的固化物的固化性组合物的方面出发,优选为聚醚多元醇,更优选为包含聚氧乙烯单元和聚氧丙烯单元的多元醇。这是因为:通过包含聚氧乙烯单元,从而在用作粘接剂时,水分能够某种程度地进入至粘接层(固化物)中,作为其结果,即便发生剥离也会抑制界面剥离,内聚破坏性高,因此能够充分发挥出作为粘接剂的功能。另外是因为:与仅以耐湿热性优异但柔软性容易不足、容易发生界面剥离的聚氧四亚甲基单元作为原料的情况相比,通过含有前述聚氧乙烯单元和聚氧丙烯单元,从而作为粘接剂的性能平衡变得优异。另外,聚氧乙烯单元和聚氧丙烯单元没必要存在于同一分子内,例如,可以将仅包含聚氧乙烯单元的多元醇和仅包含聚氧丙烯单元的多元醇组合使用,并与后述多异氰酸酯化合物(a2)发生反应。
作为前述包含聚氧乙烯单元和聚氧丙烯单元的多元醇,可列举出例如聚氧乙烯-聚氧丙烯共聚物等。作为聚氧乙烯-聚氧丙烯共聚物,从粘接性更优异的观点出发,优选为三官能以上的共聚物。另外,从用作粘接剂时对于基材的密合性、机械强度和耐湿热性的平衡优异的观点出发,聚氧乙烯中的氧乙烯单元的重复单元优选为2~10的范围。
从可获得能够形成具有优异粘接性和耐湿热性的固化物的固化性组合物的方面出发,前述包含聚氧乙烯单元和聚氧丙烯单元的多元醇中的聚氧乙烯单元与聚氧丙烯单元的质量比[(聚氧乙烯单元)/(聚氧丙烯单元)]优选为40/60~1/99的范围。
另外,作为前述包含聚氧乙烯单元和聚氧丙烯单元的多元醇,可以包含除聚氧乙烯、聚氧丙烯之外的单元(以下有时称为“其它单元”),作为前述其它单元,可列举出例如具有新戊二醇等脂肪族二元醇;甘油、三氧异丁烷、1,2,3-丁三醇、1,2,3-戊三醇、2-甲基-1,2,3-丙三醇、2-甲基-2,3,4-丁三醇、2-乙基-1,2,3-丁三醇、2,3,4-戊三醇、2,3,4-己三醇、4-丙基-3,4,5-庚三醇、2,4-二甲基-2,3,4-戊三醇、五甲基甘油、五甘油、1,2,4-丁三醇、1,2,4-戊三醇、三羟甲基丙烷等三元醇;赤藓糖醇、季戊四醇、1,2,3,4-戊四醇、2,3,4,5-己四醇、1,2,3,5-戊四醇、1,3,4,5-己四醇等四元醇;核糖醇、阿糖醇、木糖醇等五元醇;山梨醇、甘露醇、艾杜糖醇等六元醇等中的单独一种或多种作为重复单元的单元等。
进而,作为前述多元醇化合物(a1),从与基材的密合性更优异的观点出发,优选包含二~四官能成分,特别优选包含三官能成分。另外,作为多元醇(a1)的数均分子量,优选为1,000~5,000的范围,尤其是更优选为2,000~4,000的范围。
作为前述多异氰酸酯化合物(a2),优选为1分子中具有至少两个异氰酸酯基的化合物,从容易调整异氰酸酯预聚物(A)的分子量的观点出发,更优选为具有2~4个异氰酸酯基的化合物,特别优选为二异氰酸酯。
作为前述多异氰酸酯化合物(a2),可列举出例如丙烷-1,2-二异氰酸酯、2,3-二甲基丁烷-2,3-二异氰酸酯、2-甲基戊烷-2,4-二异氰酸酯、辛烷-3,6-二异氰酸酯、3,3-二硝基戊烷-1,5-二异氰酸酯、辛烷-1,6-二异氰酸酯、1,6-六亚甲基二异氰酸酯(HDI)、三甲基六亚甲基二异氰酸酯、赖氨酸二异氰酸酯、甲苯二异氰酸酯(TDI)、苯二亚甲基二异氰酸酯、四甲基间苯二亚甲基二异氰酸酯、异佛尔酮二异氰酸酯(3-异氰酸根合甲基-3,5,5-三甲基环己基异氰酸酯)、1,3-或1,4-双(异氰酸酯甲基)环己烷、二苯基甲烷-4,4’-二异氰酸酯(MDI)、二环己基甲烷-4,4’-二异氰酸酯(氢化MDI)、氢化甲苯二异氰酸酯等和它们的混合物等。这些多异氰酸酯化合物可以单独使用或组合使用2种以上。
这些之中,从容易控制与前述多元醇化合物(a1)的反应、原料获取容易性的观点出发,优选为六亚甲基二异氰酸酯、甲苯二异氰酸酯、苯二亚甲基二异氰酸酯、异佛尔酮二异氰酸酯、二苯基甲烷二异氰酸酯、二环己基甲烷-4,4’-二异氰酸酯,更优选为异佛尔酮二异氰酸酯。
作为前述多异氰酸酯化合物(a2)的用量,从容易调整所得预聚物的分子量、降低未反应多异氰酸酯的观点出发,相对于前述多元醇化合物(a1)所具有的羟基1摩尔,异氰酸酯基优选为1.80~3.50摩尔的范围。
作为前述封端化剂(a3),使用包含具有碳原子数为12个以上的烃基的酚化合物的封端化剂。从可获得能够形成具有优异粘接性和耐湿热性的固化物的固化性组合物的方面出发,碳原子数优选为12个以上且20个以下,更优选为12个以上且18个以下。另外,作为前述烃基,优选为脂肪族烃基,更优选为烷基。
作为前述具有碳原子数为12个以上的烃基的酚化合物,可列举出例如十二烷基苯酚、腰果酚、腰果二酚等。这些之中,从可获得能够形成具有优异粘接性和耐湿热性的固化物的固化性组合物的方面出发,优选为腰果酚。
作为前述封端化剂(a3),也可以使用除前述具有碳原子数为12个以上的烃基的酚化合物之外的封端化剂(以下有时称为“其它封端化剂”)。
作为前述其它封端化剂,可列举出例如丙二酸二酯(丙二酸二乙酯等)、乙酰丙酮、乙酰乙酸酯(乙酰乙酸乙酯等)等活性亚甲基化合物;乙酰肟、甲乙酮肟(MEK肟)、甲基异丁基酮肟(MIBK肟)等肟化合物;甲醇、乙醇、丙醇、丁醇、庚醇、己醇、辛醇、2-乙基己醇、异壬醇、硬脂醇等一元醇或它们的异构体;甲基甘醇、乙基甘醇、乙基二甘醇、乙基三甘醇、丁基甘醇、丁基二甘醇等二醇衍生物;二环己基胺等胺化合物;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、溴苯酚等一元酚化合物;间苯二酚、邻苯二酚、对苯二酚、双酚A、双酚S、双酚F、萘酚等二元酚化合物;ε-己内酯、ε-己内酰胺等。这些其它封端化剂可以单独使用或组合使用2种以上。
作为前述封端异氰酸酯预聚物(A)的制造方法,没有特别限定,可列举出:以多异氰酸酯化合物(a2)所具有的异氰酸酯基相对于前述多元醇化合物(a1)所具有的羟基为过量的方式发生反应,接着,使用封端化剂(a3)对过量的异氰酸酯基进行封端的方法等。
前述多元醇化合物(a1)与前述多异氰酸酯化合物(a2)的反应没有特别限定,可以通过通常的氨基甲酸酯化反应来进行。前述反应中的反应温度优选为40~140℃的范围,更优选为60~130℃的范围。另外,为了促进反应,也可以使用氨基甲酸酯聚合用催化剂。
作为前述氨基甲酸酯聚合用催化剂,可列举出例如二月桂酸二辛基锡、二月桂酸二丁基锡、辛酸亚锡、辛酸锡、辛酸铅、环烷酸铅、辛酸锌等有机金属化合物;三亚乙基二胺、三乙基胺等叔胺系化合物等。这些氨基甲酸酯聚合用催化剂可以单独使用或组合使用2种以上。
作为使用前述封端化剂(a3)进行封端的方法,可通过公知的封端化反应方法来进行,前述封端化剂(a3)的用量相对于过量的异氰酸酯基、即游离的异氰酸酯基优选为1~2当量的范围,更优选为1.05~1.5当量的范围。
基于前述封端化剂(a3)的封端化反应通常采用在氨基甲酸酯聚合的最终反应中添加封端化剂(a3)的方法,也可以在氨基甲酸酯聚合的任意阶段添加封端化剂(a3)并使其反应而得到封端异氰酸酯预聚物。
作为前述封端化剂(a3)的添加方法,可以为在规定的聚合结束时进行添加、或者在聚合初期进行添加、或者在聚合初期添加一部分并在聚合结束时添加余量等方法,优选在聚合结束时进行添加。在该情况下,作为规定的聚合结束时的基准,只要将异氰酸酯%作为基准即可。添加封端化剂时的反应温度通常为50~150℃,优选为60~120℃。反应时间通常设为1~7小时左右。在反应时,也可以添加前述氨基甲酸酯聚合用催化剂来促进反应。另外,在反应时,可以添加任意量的增塑剂。
作为前述封端异氰酸酯预聚物(A)的重均分子量,从将固化性组合物用作粘接剂时的处理良好的观点出发,优选为4,000~15,000的范围,更优选为5,000~10,000的范围。需要说明的是,在本发明中,重均分子量(Mw)是通过凝胶渗透色谱(GPC)而测得的值。
作为前述环氧树脂(B),没有特别限定,可以使用各种环氧树脂。在用作粘接剂的情况下,优选在常温下为液体的环氧树脂,可列举出例如四甲基联苯酚型环氧树脂、双酚A型环氧树脂、双酚F型环氧树脂等双酚型或联苯酚型环氧树脂;丁二醇二缩水甘油醚、新戊二醇二缩水甘油醚、己二醇二缩水甘油醚、三羟甲基丙烷三缩水甘油醚、甘油三缩水甘油醚等脂肪族多元醇聚缩水甘油醚;二缩水甘油基苯胺、间苯二酚二缩水甘油醚、氢化双酚A二缩水甘油醚等含有环结构的多缩水甘油基化合物;烷基苯酚单缩水甘油醚等含有环结构的单官能缩水甘油基化合物;新癸酸缩水甘油酯等聚缩水甘油酯化合物等。这些之中,从可获得能够形成具有优异粘接性和耐湿热性的固化物的固化性组合物的方面出发,优选使用双酚型或联苯酚型环氧树脂,从工业获取容易性的观点出发,优选为双酚型环氧树脂。尤其是,双酚型环氧树脂相对于环氧树脂(B)的总质量的比例优选为50质量%以上,更优选为70质量%以上。另外,这些环氧树脂可以分别单独使用,也可以组合使用2种以上。
作为前述双酚型或联苯酚型环氧树脂,可列举出例如以各种双酚化合物或联苯酚化合物且以表卤代醇作为树脂原料而得到的树脂,具体而言,可列举出下述结构式(1)所示的树脂。这些双酚型或联苯酚型环氧树脂可以分别单独使用,也可以组合使用2种以上。
[式中,X各自独立地为下述结构式(2-1)~(2-8)中任意者所示的结构部位,n表示重复数。]
(式中,R2各自独立地为氢原子、碳原子数1~4的烷基、碳原子数1~4的烷氧基中的任意者,R3各自独立地为碳原子数1~4的烷基、碳原子数1~4的烷氧基中的任意者。)
前述结构式(1)中的X为前述结构式(2-1)~(2-8)中任意者所示的结构部位,在分子中存在多个的X可以为相同的结构部位,也可以为彼此不同的结构部位。这些之中,从可获得能够形成具有优异粘接性和耐湿热性的固化物的固化性组合物的方面出发,优选为通式(2-1)或(2-2)所示的结构部位。
如上所述,前述双酚型或联苯酚型环氧树脂可通过以各种双酚化合物或联苯酚化合物且以表卤代醇作为树脂原料的方法等来制造。具体而言,可列举出:使通过使双酚化合物或联苯酚化合物与表卤代醇发生反应而得到的二缩水甘油醚化合物进一步与双酚化合物或联苯酚化合物发生反应的方法(方法1);使双酚化合物或联苯酚化合物与表卤代醇发生反应而直接得到环氧树脂的方法(方法2)等。这些之中,从容易控制反应、容易将所得环氧树脂(B)的环氧当量控制为前述优选值的方面出发,优选为前述方法1。
前述方法1或2中使用的双酚化合物或联苯酚化合物可列举出例如下述结构式(3-1)~(3-8)中任意者所示的化合物等。
(式中,R2各自独立地为氢原子、碳原子数1~4的烷基、碳原子数1~4的烷氧基中的任意者,R3各自独立地为碳原子数1~4的烷基、碳原子数1~4的烷氧基中的任意者。)
这些双酚化合物或联苯酚化合物可以单独使用或组合使用2种以上。这些之中,从可获得能够形成具有优异粘接性和耐湿热性的固化物的固化性组合物的方面出发,优选为通式(3-1)或(3-2)所示的化合物。
关于前述方法1,关于双酚化合物或联苯酚化合物与这些二缩水甘油醚化合物的反应比例,两者的质量比优选为50/50~5/95的范围。反应温度优选为120~160℃左右,可以使用四甲基氯化铵等反应催化剂。
从可获得能够形成具有优异粘接性和耐湿热性的固化物的固化性组合物的方面出发,前述环氧树脂(B)的环氧当量优选为150~250g/eq的范围,优选为160~200g/eq的范围。
另外,作为前述环氧树脂(B),根据需要也可以将双酚型或联苯酚型环氧树脂与氨基甲酸酯改性环氧树脂、橡胶改性环氧树脂等柔软性环氧树脂组合使用。
作为前述氨基甲酸酯改性环氧树脂,只要是分子中具有氨基甲酸酯键和2个以上环氧基的树脂,则作为其结构就没有特别限定。从能够有效地向1分子中导入氨基甲酸酯键和环氧基的观点出发,优选为使具有异氰酸酯基且含有氨基甲酸酯键的化合物与含有羟基的环氧化合物发生反应而得到的树脂,所述具有异氰酸酯基且含有氨基甲酸酯键的化合物是使多羟基化合物与多异氰酸酯发生反应而得到的。
作为前述多羟基化合物,可列举出例如聚醚多元醇、聚酯多元醇、羟基羧酸与环氧烷烃的加成物、聚丁二烯多元醇、聚烯烃多元醇等。
前述多羟基化合物的重均分子量优选为300~5,000的范围,更优选为500~2,000的范围。
前述多异氰酸酯只要是具有2个以上异氰酸酯基的化合物,就没有特别限定。可列举出例如脂肪族多异氰酸酯、芳香族多异氰酸酯、具有芳香族烃基的多异氰酸酯等。这些之中,优选为芳香族多异氰酸酯。作为前述芳香族多异氰酸酯,可列举出例如甲苯二异氰酸酯、二苯基甲烷二异氰酸酯、萘二异氰酸酯等。
通过上述反应,得到在末端具有游离异氰酸酯基的氨基甲酸酯预聚物。通过使其与1分子中具有至少1个羟基的环氧树脂(例如双酚A的二缩水甘油醚、双酚F的二缩水甘油醚、脂肪族多元醇的二缩水甘油醚和缩水甘油等)发生反应而得到氨基甲酸酯改性环氧树脂。
前述氨基甲酸酯改性环氧树脂的环氧当量优选为200~250g/eq的范围。
前述橡胶改性环氧树脂只要为具有2个以上环氧基且骨架为橡胶的环氧树脂,就没有特别限定。作为形成骨架的橡胶,可列举出例如聚丁二烯、丙烯腈丁二烯橡胶(NBR)、羧基末端NBR(CTBN)等。前述橡胶改性环氧树脂可以单独使用或组合使用2种以上。
前述橡胶改性环氧树脂的环氧当量优选为200~350g/eq的范围。另外,前述橡胶改性环氧树脂的制造方法没有特别限定,可列举出例如在大量的环氧中使橡胶与环氧发生反应来制造的方法等。在制造橡胶改性环氧树脂时使用的环氧(例如环氧树脂)没有特别限定。
作为前述固化剂(C),可列举出例如多胺化合物、酰胺化合物、酸酐、含有酚性羟基的树脂、磷化合物、咪唑化合物、咪唑啉化合物、脲系化合物、有机酸金属盐、路易斯酸、胺络盐等。
作为前述多胺化合物,可列举出例如三亚甲基二胺、乙二胺、N,N,N’,N’-四甲基乙二胺、五甲基二亚乙基三胺、三亚乙基二胺、二亚丙基二胺、N,N,N’,N’-四甲基亚丙基二胺、四亚甲基二胺、戊二胺、六亚甲基二胺、三甲基六亚甲基二胺、N,N,N’,N’-四甲基六亚甲基二胺、N,N-二甲基环己胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺、二甲基氨基丙基胺、二乙基氨基丙基胺、二丁基氨基丙基胺、1,4-二氮杂双环(2,2,2)辛烷(三亚乙基二胺)、聚氧乙烯二胺(polyoxyethylene diamine)、聚氧丙烯二胺(polyoxypropylene diamine)、双(2-二甲基氨基乙基)醚、二甲基氨基乙氧基乙氧基乙醇、三乙醇胺、二甲基氨基己醇等脂肪族胺化合物;
哌啶、哌嗪、薄荷烷二胺、异佛尔酮二胺、甲基吗啉、乙基吗啉、N,N’,N”-三(二甲基氨基丙基)六氢均三嗪、3,9-双(3-氨基丙基)-2,4,8,10-四氧杂螺(5,5)十一烷加合物、N-氨基乙基哌嗪、三甲基氨基乙基哌嗪、双(4-氨基环己基)甲烷、N,N’-二甲基哌嗪、1,8-二氮杂双环-[5.4.0]-十一碳烯(DBU)等脂环式和杂环式胺化合物;
邻苯二胺、间苯二胺、对苯二胺、二氨基二苯基甲烷、二氨基二苯基砜、苄基甲基胺、二甲基苄基胺、间苯二甲胺、吡啶、甲基吡啶、α-甲基苄基甲基胺等芳香族胺化合物;
环氧化合物加成多胺、迈克尔加成多胺、曼尼希加成多胺、硫脲加成多胺、酮封端链多胺、双氰胺、胍、有机酸酰肼、二氨基马来腈、胺化酰亚胺(aminimide)、三氟化硼-哌啶络合物、三氟化硼-单乙基胺络合物等改性胺化合物等。
作为前述酰胺化合物,可列举出例如双氰胺、聚酰胺胺等。作为前述聚酰胺胺,可列举出例如使琥珀酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸等脂肪族二羧酸、脂肪酸、二聚酸等羧酸化合物与脂肪族多胺、具有聚氧亚烷基链的多胺等发生反应而得到的物质等。
作为前述酸酐,可列举出例如苯二甲酸酐、偏苯三酸酐、均苯四酸酐、马来酸酐、四氢苯二甲酸酐、甲基四氢苯二甲酸酐、甲基纳迪克酸酐、六氢苯二甲酸酐、甲基六氢苯二甲酸酐等。
作为前述含有酚性羟基的树脂,可列举出例如苯酚酚醛清漆树脂、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树脂)、萘酚芳烷基树脂、三羟甲基甲烷树脂、四羟苯基乙烷树脂、萘酚酚醛清漆树脂、萘酚-苯酚共缩酚醛清漆树脂、萘酚-甲酚共缩酚醛清漆树脂、联苯改性酚醛树脂(用双亚甲基连接苯酚核而得到的多元苯酚化合物)、联苯改性萘酚树脂(用双亚甲基连接苯酚核而得到的多元萘酚化合物)、氨基三嗪改性酚醛树脂(用三聚氰胺、苯并胍胺等连接苯酚核而得到的多元苯酚化合物)、含烷氧基芳香环改性酚醛清漆树脂(用甲醛连接苯酚核和含烷氧基芳香环而得到的多元苯酚化合物)等多元酚化合物等。
作为前述磷化合物,可列举出例如乙基膦、丁基膦等烷基膦;苯基膦等伯膦;二甲基膦、二丙基膦等二烷基膦;二苯基膦、甲基乙基膦等仲膦;三甲基膦、三乙基膦、三苯基膦等叔膦等。
作为前述咪唑化合物,可列举出例如咪唑、1-甲基咪唑、2-甲基咪唑、3-甲基咪唑、4-甲基咪唑、5-甲基咪唑、1-乙基咪唑、2-乙基咪唑、3-乙基咪唑、4-乙基咪唑、5-乙基咪唑、1-正丙基咪唑、2-正丙基咪唑、1-异丙基咪唑、2-异丙基咪唑、1-正丁基咪唑、2-正丁基咪唑、1-异丁基咪唑、2-异丁基咪唑、2-十一烷基-1H-咪唑、2-十七烷基-1H-咪唑、1,2-二甲基咪唑、1,3-二甲基咪唑、2,4-二甲基咪唑、2-乙基-4-甲基咪唑、1-苯基咪唑、2-苯基-1H-咪唑、4-甲基-2-苯基-1H-咪唑、2-苯基-4-甲基咪唑、1-苄基-2-甲基咪唑、1-苄基-2-苯基咪唑、1-氰基乙基-2-甲基咪唑、1-氰基乙基-2-乙基-4-甲基咪唑、1-氰基乙基-2-十一烷基咪唑、1-氰基乙基-2-苯基咪唑、2-苯基咪唑异氰脲酸加成物、2-甲基咪唑异氰脲酸加成物、2-苯基-4,5-二羟基甲基咪唑、2-苯基-4-甲基-5-羟基甲基咪唑、1-氰基乙基-2-苯基-4,5-二(2-氰基乙氧基)甲基咪唑、1-十二烷基-2-甲基-3-苄基氯化咪唑鎓、1-苄基-2-苯基咪唑盐酸盐等。
作为前述咪唑啉化合物,可列举出例如2-甲基咪唑啉、2-苯基咪唑啉等。
作为前述脲化合物,可列举出例如对氯苯基-N,N-二甲基脲、3-苯基-1,1-二甲基脲、3-(3,4-二氯苯基)-N,N-二甲基脲、N-(3-氯-4-甲基苯基)-N’,N’-二甲基脲等。
这些固化剂可以单独使用或组合使用2种以上。这些之中,从可获得能够形成具有优异粘接性和耐湿热性的固化物的固化性组合物的方面出发,优选为双氰胺。
本发明中,作为前述封端异氰酸酯预聚物(A)与环氧树脂(B)的使用比例,从可获得能够形成具有优异粘接性和耐湿热性的固化物的固化性组合物的方面出发,以(A)/(B)所示的质量比计,优选为5/95~40/60的范围,更优选为10/90~30/70的范围。另外,关于环氧树脂(B)与前述固化剂(C)的配混比例,在使用具有能够与环氧基发生反应的官能团的固化剂的情况下,优选以前述固化剂中的官能团相对于环氧树脂(B)的环氧基1摩尔成为0.5~1.1摩尔这一范围的比例进行配混。另外,可以使用固化促进剂,在使用前述固化促进剂的情况下,相对于前述环氧树脂(B)100质量份,优选以0.5~10质量份的比例进行配混。
作为本发明的固化性组合物,根据需要可以含有有机溶剂、紫外线吸收剂、抗氧化剂、硅系添加剂、氟系添加剂、阻燃剂、增塑剂、硅烷偶联剂、有机珠、无机微粒、无机填料、流变控制剂、脱泡剂、防雾剂、着色剂等。这些各种成分可以根据期望性能而添加任意量。
作为本发明的固化性组合物的制备方法,可通过使用罐磨机(pot mill)、球磨机、珠磨机、辊磨机、均化器、SUPERMILL、均质分散器、万能搅拌器、班伯里密炼机、捏合机等,将前述封端异氰酸酯预聚物(A)、环氧树脂(B)、固化剂(C)和根据需要可含有的前述各种任选成分进行均匀混合的方法来制备。
本发明的固化性组合物的用途没有特别限定,可以用于涂料、涂布剂、成形材料、绝缘材料、封固剂、密封剂、纤维的成束剂等各种用途。这些之中,活用固化物的柔软性和韧性优异的特征,可适合地用作汽车、电车、土木建筑、电子产品、飞机、宇宙产业领域的结构构件的粘接剂。
本发明的粘接剂即使用于例如金属-非金属间那样的不同原材料的粘接的情况下,也可以不受温度环境变化的影响而维持高的粘接性,不易产生剥离等。另外,本发明的粘接剂除了结构构件用途之外,还可以用作一般办公用途、医疗用途、碳纤维、电子材料用途等的粘接剂,作为电子材料用粘接剂,可列举出例如积层基板等多层基板的层间粘接剂、光学部件接合用粘接剂、光盘贴合用粘接剂、印刷电路板安装用粘接剂、芯片接合粘接剂、底部填充材料等半导体用粘接剂;BGA增强用底部填充材料、各向异性导电性薄膜、各向异性导电性糊剂等安装用粘接剂等。
实施例
以下,通过实施例和比较例来具体说明本发明。需要说明的是,本发明不限定于以下列举的实施例。
需要说明的是,在本实施例中,重均分子量(Mw)是使用凝胶渗透色谱(GPC),并利用下述条件而测得的值。
测定装置:东曹公司制HLC-8220
柱:东曹公司制的保护柱HXL-H
+东曹公司制TSKgel G5000HXL
+东曹公司制TSKgel G4000HXL
+东曹公司制TSKgel G3000HXL
+东曹公司制TSKgel G2000HXL
检测器:RI(差示折射计)
数据处理:东曹公司制SC-8010
测定条件:柱温度40℃
溶剂四氢呋喃
流速1.0ml/分钟
标准:聚苯乙烯
试样:将按照树脂固体成分换算计为0.4质量%的四氢呋喃溶液用微过滤器进行过滤而得到的物质(100μl)
(合成例1:封端异氰酸酯预聚物(1)合成)
在氮气气氛下,将作为聚氧乙烯-聚氧丙烯共聚物的聚醚多元醇(三井化学&SKC聚氨酯公司制的“ACTCOL EP-530”、Mn:3000、官能团数量:3)638质量份、异佛尔酮二异氰酸酯(Sumika Covestro Urethane公司制的“Desmodur I”)142质量份进行混合,投入二乙酸二辛基锡(日东化成公司制的“NEOSTANN U-820”)0.1质量份作为催化剂,在80℃下使其反应5小时,接着,投入腰果酚(Cardolite公司制的“NX2021”)220质量份作为封端化剂,在90℃下使其反应5小时,得到封端异氰酸酯预聚物(1)。
(合成例2~13:封端异氰酸酯预聚物(2)~(13)的合成)
按照下述表1所示的比例来配混各成分,利用与合成例1相同的方法,得到封端异氰酸酯预聚物(2)~(13)。
将合成例1~13中调整的封端异氰酸酯预聚物的组成示于表1和表2。
[表1]
[表2]
表1和2中的简写表示以下的物质。
EP-530:聚氧乙烯-聚氧丙烯共聚物(三井化学&SKC聚氨酯公司制的“EP-530”、Mw:3000、官能团数量:3)
ED-37A:聚氧乙烯-聚氧丙烯共聚物(三井化学&SKC聚氨酯公司制的“ED-37A”、Mw:3000、官能团数量:2)
T-3000:聚丙二醇(三井化学&SKC聚氨酯公司制的“T-3000”、Mw:3000、官能团数量:3)
EP-3033:聚丙二醇(三井化学&SKC聚氨酯公司制的“EP-3033”、Mw:6600、官能团数量:4)
PTMG-3000:聚四亚甲基二醇(三菱化学公司制的“PTMG-3000”、Mw:3000、官能团数量:2)
T5652:聚碳酸酯多元醇(旭化成公司制的“DURANOL T5652”、Mw:2000、官能团数量:2)
D-3000:聚丙二醇(三井化学&SKC聚氨酯公司制的“D-3000”、Mw:3000、官能团数量:2)
IPDI:异佛尔酮二异氰酸酯(Sumika Covestro Urethane公司制的“Desmodur I”)
TDI:甲苯二异氰酸酯(三井化学&SKC聚氨酯公司制的“T-80”)
HDI:六亚甲基二异氰酸酯(Sumika Covestro Urethane公司制的“Desmodur H”)
H12MDI:二环己基甲烷-4,4’-二异氰酸酯(Sumika Covestro Urethane公司制的“Desmodur W”)
PDDP:对十二烷基苯酚(SI Group公司制的“Para-Dodecylphenol”、具有碳原子数为12个的烃基的酚化合物)
NX-2021:腰果酚(Cardolite公司制的“NX-2021”、具有碳原子数为15个的烃基的酚化合物)
NX-2026:腰果酚(Cardolite公司制的“NX-2026”、具有碳原子数为15个的烃基的酚化合物)
PTBP:对叔丁基苯酚(DIC公司制的“DIC-PTBP”)
PNP:对壬基苯酚(SI Group公司制的“Tech.grade”)
(实施例1:固化性组合物(1)的制备)
将合成例1中得到的封端异氰酸酯预聚物(1)20质量份、橡胶改性环氧树脂(DIC公司制的“EPICLON TSR-601”)5质量份、双酚A型环氧树脂(DIC公司制的“EPICLON 850-S”)75质量份、作为固化剂的双氰胺5质量份、作为固化促进剂的3,4-二氯苯基-N,N-二甲基脲1质量份、作为填料的碳酸钙20质量份进行混合,得到固化性组合物(1)。
(实施例2~8:固化性组合物(2)~(8)的制备)
代替实施例1中使用的封端异氰酸酯预聚物(1),以表3所示的配混量使用合成例2~8中得到的封端异氰酸酯预聚物(2)~(8),除此之外,与实施例1同样操作,得到固化性组合物(2)~(8)。
(比较例2:固化性组合物(R1)的制备)
代替实施例1中使用的封端异氰酸酯预聚物(1),以表4所示的配混量使用合成例9~13中得到的封端异氰酸酯预聚物(9)~(13),除此之外,与实施例1同样操作,得到固化性组合物(R1)~(R8)。
使用上述实施例和比较例中得到的固化性组合物(1)~(8)和(R1)~(R8),进行下述评价。
[粘接性的评价方法]
粘接性的评价根据拉伸剪切试验和T字剥离试验来进行。
<试验片的制作>
按照JIS K6859(1994)(粘接剂的蠕变破坏试验)和JIS K6854-3(1999)(粘接剂的剥离粘接强度试验),使实施例和比较例中得到的固化性组合物在170℃下固化30分钟,得到拉伸剪切试验和T字剥离试验用的试验片。
<拉伸剪切试验>
按照JIS K6859(1994)(粘接剂的蠕变破坏试验)方法,在25℃的条件下,使用岛津制作所制的“AUTOGRAPH AG-XPlus 100kN”,测定前述试验片的拉伸剪切强度。
<T字剥离试验>
按照JIS K6854-3(1999)(粘接剂的剥离粘接强度试验)方法,在25℃的条件下,使用岛津制作所制的“AUTOGRAPH AG-IS 1kN”,测定前述试验片的剥离强度。
[耐湿热性的评价方法]
将上述<拉伸剪切试验><T字剥离试验>中使用的试验片在50℃、90%的条件下进行2星期的耐湿热试验后,利用相同的试验机,按照上述<拉伸剪切试验>中记载的方法来测定拉伸剪切强度。
[内聚破坏面积比率(CF面积比率)的确认方法]
针对上述<拉伸剪切试验>中使用的试验片和耐湿热试验后的<拉伸剪切试验>的试验片,通过目视来确认内聚破坏面积比率(CF面积比率),确认试验片的破坏状态。前述内聚破坏面积比率越高,则破坏状态越良好。另外,即便在耐湿热试验后,内聚破坏面积比率高的试验片的耐湿热性也优异。
将实施例1~8中制作的固化性组合物(1)~(8)和比较例1~5中制作的固化性组合物(R1)~(R5)的组成和评价结果示于表3和4。
[表3]
[表4]
表3和4中的简写表示以下的物质。
TSR-601:橡胶改性环氧树脂(DIC公司制的“EPICLON TSR-601”)
850-S:双酚A型环氧树脂(DIC公司制的“EPICLON 850-S”)
830-S:双酚F型液状环氧树脂(DIC公司制的“EPICLON 830-S”、环氧当量:170g/eq)
DICY:双氰胺
DCMU:3,4-二氯苯基-N,N-二甲基脲
表3中示出的实施例1~8是包含使用具有碳原子数为12个以上的烃基的酚化合物作为封端化剂而得到的封端异氰酸酯预聚物的固化性组合物的例子。可确认:这些固化性组合物具有优异的粘接性和耐湿热性。
另一方面,表4中示出的比较例1~5是包含不使用具有碳原子数为12个以上的烃基的酚化合物作为封端化剂的封端异氰酸酯预聚物的固化性组合物的例子。可确认:这些固化性组合物的粘接性不充分,在耐湿热性方面也不充分。
Claims (11)
1.一种固化性组合物,其特征在于,含有封端异氰酸酯预聚物(A)、环氧树脂(B)和固化剂(C),所述封端异氰酸酯预聚物(A)以多元醇化合物(a1)、多异氰酸酯化合物(a2)、封端化剂(a3)作为必须原料,
所述封端化剂(a3)包含具有碳原子数为12个以上的烃基的酚化合物。
2.根据权利要求1所述的固化性组合物,其中,所述多元醇化合物(a1)为聚醚多元醇。
3.根据权利要求1或2所述的固化性组合物,其中,所述多元醇化合物(a1)包含聚氧乙烯单元和聚氧丙烯单元。
4.根据权利要求1~3中任一项所述的固化性组合物,其中,所述多元醇化合物(a1)为聚氧乙烯-聚氧丙烯共聚物。
5.根据权利要求1~4中任一项所述的固化性组合物,其中,所述多异氰酸酯化合物(a2)为二异氰酸酯。
6.根据权利要求1~5中任一项所述的固化性组合物,其中,所述具有碳原子数为12个以上的烃基的酚化合物为腰果酚。
7.根据权利要求1~6中任一项所述的固化性组合物,其中,所述固化剂(C)包含双氰胺。
8.根据权利要求1~7中任一项所述的固化性组合物,其中,所述环氧树脂(B)的环氧当量为150~250g/eq的范围。
9.根据权利要求1~8中任一项所述的固化性组合物,其中,所述封端异氰酸酯预聚物(A)与所述环氧树脂(B)的质量比例[(A)/(B)]为10/90~30/70的范围。
10.一种固化物,其为权利要求1~9中任一项所述的固化性组合物的固化物。
11.一种粘接剂,其由权利要求1~9中任一项所述的固化性组合物形成。
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