CN103732642B - 新型的氰酸酯化合物及其制造方法、以及包含该化合物的固化性树脂组合物及其固化物 - Google Patents
新型的氰酸酯化合物及其制造方法、以及包含该化合物的固化性树脂组合物及其固化物 Download PDFInfo
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- CN103732642B CN103732642B CN201280039167.8A CN201280039167A CN103732642B CN 103732642 B CN103732642 B CN 103732642B CN 201280039167 A CN201280039167 A CN 201280039167A CN 103732642 B CN103732642 B CN 103732642B
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- curable resin
- cyanate esters
- phenol
- cyanic acid
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- 239000011342 resin composition Substances 0.000 title claims abstract description 53
- -1 cyanic acid ester compound Chemical class 0.000 title claims abstract description 38
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 23
- OIAUFEASXQPCFE-UHFFFAOYSA-N formaldehyde;1,3-xylene Chemical class O=C.CC1=CC=CC(C)=C1 OIAUFEASXQPCFE-UHFFFAOYSA-N 0.000 claims abstract description 41
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 86
- 239000004643 cyanate ester Substances 0.000 claims description 68
- 238000000034 method Methods 0.000 claims description 68
- 150000001913 cyanates Chemical class 0.000 claims description 63
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- 150000001875 compounds Chemical class 0.000 claims description 35
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- 229920005989 resin Polymers 0.000 claims description 33
- 239000011347 resin Substances 0.000 claims description 33
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 14
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- UIFVCPMLQXKEEU-UHFFFAOYSA-N 2,3-dimethylbenzaldehyde Chemical compound CC1=CC=CC(C=O)=C1C UIFVCPMLQXKEEU-UHFFFAOYSA-N 0.000 description 4
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 4
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Abstract
本发明提供一种新型的氰酸酯化合物及其制造方法、以及使用了其的固化性树脂组合物等,所述新型的氰酸酯化合物能够实现介电常数和介电损耗角正切低、且具有优异的阻燃性和耐热性的固化物,而且粘度较低且具有优异的溶剂溶解性,处理性也优异。将酚改性二甲苯甲醛树脂进行氰酸酯化。
Description
技术领域
本发明涉及新型的氰酸酯化合物及其制造方法、以及包含该化合物的固化性树脂组合物及其固化物。
背景技术
氰酸酯化合物通过固化而产生三嗪环,由于其高耐热性和优异的电特性,一直以来作为各种功能性高分子材料的原料而广泛用于结构用复合材料、粘接剂、电气用绝缘材料、电气电子部件等。然而,近年来,随着这些应用领域中所要求的性能的高度化,作为功能性高分子材料而要求的各物性变得更加严格。作为所述物性,例如可列举出阻燃性、耐热性、低介电常数、低介电损耗角正切、耐候性、耐化学试剂性、低吸水性、高断裂韧性等。然而,截止至今,这些要求物性并没有得到满足。
例如,在印刷电路板材料的领域中,随着通信频率、时钟频率的高频化,要求更低的介电常数和介电损耗角正切。因此,近年来,广泛使用介电特性优异的氰酸酯树脂。
另外,从确保相对于火灾的安全性的观点出发,为了赋予阻燃性而使用了具有高阻燃性的溴化合物。作为这种溴化合物,例如已知有溴化双酚A(参照专利文献1)、溴化苯酚酚醛清漆的缩水甘油醚(参照专利文献2)、溴化马来酰亚胺类(参照专利文献3)、具有溴的单官能氰酸酯化合物(参照专利文献4)、与氰酸酯化合物不具有反应性的添加型溴化合物(参照专利文献5)等。
然而,这些溴化合物虽然具有高阻燃性,但其不仅会因热分解而形成腐蚀性的溴、溴化氢,而且在氧的存在下分解时还可能形成与近年来的二噁英问题有关的毒性强的溴化合物。因此,寻求不包含这些溴系阻燃剂的材料。
因而,作为代替溴的阻燃剂,研究了含磷化合物、含氮或含硫化合物。例如,作为经常配混在环氧树脂中的含磷化合物,已知有磷酸三苯酯、间苯二酚双(二苯基磷酸酯)等。
然而,将这些含磷化合物大量配混在树脂组合物中时,大多会使树脂组合物的耐热性、耐湿性、吸水性等降低。为了对其进行改善,还研究了将具有酚羟基的含磷化合物与二价的氰酸酯化合物组合使用(例如,参照专利文献6、专利文献7、专利文献8),但含磷化合物的使用与上述溴化合物同样地存在毒性的问题。而且,含磷化合物大多难以进行填埋处理,还担心在燃烧时产生磷化氢气体。另外,作为含氮化合物,已知有三聚氰胺、胍等,但其单独使用时阻燃性不充分。
另一方面,作为对树脂组合物赋予阻燃性的其它成分,已知有氢氧化铝、氢氧化镁等金属氢氧化物。然而,金属氢氧化物的配混有可能招致树脂组合物的介电特性、耐热性、耐冲击性、成型性的降低。另外,进行了如下尝试:例如在环氧树脂中使用那样地通过大量使用球状熔融二氧化硅等无机填料,减少可燃成分,由此确保阻燃性。然而,无机填料的大量配混有可能使树脂组合物的熔融粘度上升、因成型性的降低或与基材的润湿性降低而导致粘接力的降低、进而使介电特性恶化等。另外,还尝试了将三氧化锑等锑系阻燃剂与溴化环氧树脂组合使用。然而,锑系阻燃剂通常为有害物质,因此担心其慢性毒性。
从以上观点出发,比以往更加要求提高在树脂组合物中配混的功能性高分子材料自身的阻燃性。
另外,为了与阻燃性同时地改善耐热性、低介电常数、低介电损耗角正切、耐候性、耐化学试剂性、低吸水性、高断裂韧性、成型性、粘接性等,一直以来进行了多种尝试。例如已知有如下方法:通过将单官能氰酸酯化合物与2官能氰酸酯化合物进行组合,从而制作热稳定性优异的固化物的方法(参照专利文献9);通过将单官能氰酸酯化合物与多官能氰酸酯化合物进行组合,从而实现低介电常数化和低介电损耗角正切化的方法(参照专利文献10)。
另外,已知有如下方法:通过添加含有卤素的单官能氰酸酯化合物,从而制造可实现低介电常数化和低介电损耗角正切化、且吸湿性低的阻燃性氰酸酯固化树脂组合物的方法(参照专利文献4)。该专利文献4中虽然记载了各种氰酸酯化合物,但为了保证阻燃性,必须使用具有溴作为官能基团的芳香族单官能氰酸酯化合物,不使用溴就无法成功地提高阻燃性。
进而,专利文献11中记载了使用芳香族氰酸酯化合物来实现阻燃化的方法,所述芳香族氰酸酯化合物具有至少2个介由含不饱和基的基团连接的环,专利文献12中记载了使用含氟二氰酸酯化合物来实现阻燃化的方法,专利文献13中记载了使用苯酚酚醛清漆型氰酸酯化合物来实现阻燃化的方法。
然而,这些方法均无法获得高维地具备介电特性、阻燃性、耐热性的所有性能的实用的氰酸酯化合物单体的固化物。
另一方面,芳烷基结构的氰酸酯化合物已知其固化物具有低介电特性、高阻燃性、高耐热性(参照专利文献14)。
现有技术文献
专利文献
专利文献1:日本特公平4-24370号公报
专利文献2:日本特开平2-286723号公报
专利文献3:日本特开平7-207022号公报
专利文献4:日本特开平6-122763号公报
专利文献5:日本特开2000-95938号公报
专利文献6:日本特开2003-128928号公报
专利文献7:日本特开2003-128753号公报
专利文献8:日本特开2003-128784号公报
专利文献9:日本特开平6-228308号公报
专利文献10:日本特开平6-49238号公报
专利文献11:日本特表2002-531989号公报
专利文献12:日本特开昭63-250359号公报
专利文献13:日本特开2002-206048号公报
专利文献14:日本特开2005-264154号公报
发明内容
发明要解决的问题
然而,上述专利文献14中记载的芳烷基结构的氰酸酯化合物难溶于溶剂,另外固形物的粘度高、难以处理。一般使用氰酸酯化合物来形成印刷电路板用途等的层压板时,采取如下工序:首先溶于甲基乙基酮等溶剂来制备清漆,然后将其浸渗于玻璃布并使其干燥,从而制作预浸料,因此氰酸酯化合物的溶剂溶解性、粘性、稳定性也成为重要的因素。
本发明的课题在于,提供能够实现介电常数和介电损耗角正切低、且具有优异的阻燃性和耐热性的固化物、而且粘度较低且具有优异的溶剂溶解性、处理性也优异的新型的氰酸酯化合物及其实用的制造方法。
另外,本发明的其它课题在于提供包含所述新型的氰酸酯化合物的固化性树脂组合物、预浸料、层压板、密封用材料、纤维强化复合材料以及粘接剂等,进而提供介电常数和介电损耗角正切低、具有优异的阻燃性和耐热性、处理性也优异的固化物。
用于解决问题的方案
本发明人等为了解决上述课题而反复进行了深入研究,结果发现,将酚改性二甲苯甲醛树脂进行氰酸酯化而得到的氰酸酯的粘度较低且具有优异的溶剂溶解性、处理性优异,以及使用了该氰酸酯化合物的固化性树脂组合物出人意料地能够实现介电常数和介电损耗角正切低、且具有优异的阻燃性和耐热性的固化物等,从而完成了本发明。
即,本发明提供以下<1>~<16>。
<1>一种氰酸酯化合物,其是将酚改性二甲苯甲醛树脂进行氰酸酯化而得到的。
<2>根据上述<1>所述的氰酸酯化合物,其具有下述通式(I)所示的结构,
(式中,R1各自独立地表示亚甲基、亚甲基氧基、亚甲基氧基亚甲基或氧基亚甲基;R2~R4各自独立地表示氢原子、碳原子数为1~3的烷基(优选为甲基)、羟基或羟基亚甲基;T1表示氢原子、羟基或羟基亚甲基;x各自独立地表示0~4的整数(优选为0~2的整数);y和z各自独立地表示0~3的整数(优选为0~2的整数);w表示0或1的整数;m表示0以上的整数;n1和n2各自独立地表示1以上的整数。)。
<3>根据上述<1>或<2>所述的氰酸酯化合物,其中,前述酚改性二甲苯甲醛树脂是用下述通式(1)所示的酚类将二甲苯甲醛树脂进行改性而成的,
(式中,Ar表示芳香环,R表示芳香环上的所有氢原子或一价的取代基,一价的取代基为烷基或芳基,芳香环上多个存在的R彼此可以相同也可以不同,其中,R中的至少一个为氢原子。)。
<4>根据上述<3>所述的氰酸酯化合物,其中,前述通式(1)所示的酚类为苯酚和/或2,6-二甲酚。
<5>根据上述<1>~<4>中任一项所述的氰酸酯化合物,其中,重均分子量Mw为250~10,000。
<6>一种氰酸酯化合物,其具有下述通式(I)所示的结构,
(式中,R1各自独立地表示亚甲基、亚甲基氧基、亚甲基氧基亚甲基或氧基亚甲基;R2~R4各自独立地表示氢原子、碳原子数为1~3的烷基(优选为甲基)、羟基或羟基亚甲基;T1表示氢原子、羟基或羟基亚甲基;x各自独立地表示0~4的整数(优选为0~2的整数);y和z各自独立地表示0~3的整数(优选为0~2的整数);w表示0或1的整数;m表示0以上的整数;n1和n2各自独立地表示1以上的整数。)。
<7>根据上述<6>所述的氰酸酯化合物,其中,重均分子量Mw为250~10,000。
<8>一种上述<1>~<5>中任一项所述的氰酸酯化合物的制造方法,其具有:
将二甲苯甲醛树脂进行酚改性的工序;以及
将所得酚改性二甲苯甲醛树脂所具有的酚羟基进行氰酸酯化的工序。
<9>一种固化性树脂组合物,其包含上述<1>~<7>中任一项所述的氰酸酯化合物。
<10>根据上述<9>所述的固化性树脂组合物,其还包含选自由上述<1>~<7>中任一项所述的氰酸酯化合物以外的氰酸酯化合物、环氧树脂、氧杂环丁烷树脂以及具有可聚合的不饱和基团的化合物组成的组中的至少1种以上。
<11>一种固化物,其是使上述<9>或<10>所述的固化性树脂组合物进行固化而成的。
<12>一种预浸料,其是将上述<9>或<10>所述的固化性树脂组合物浸渗或涂布于纤维基材并使其干燥而成的。
<13>一种层压板,其是在上述<12>所述的预浸料上层叠金属箔并加热加压成型而成的。
<14>一种密封用材料,其包含上述<9>或<10>所述的固化性树脂组合物。
<15>一种纤维强化复合材料,其包含上述<9>或<10>所述的固化性树脂组合物。
<16>一种粘接剂,其包含上述<9>或<10>所述的固化性树脂组合物。
发明的效果
根据本发明,能够实现粘度较低且具有优异的溶剂溶解性、处理性优异的新型的氰酸酯化合物。另外,通过使用该氰酸酯化合物,能够实现具有优异的阻燃性、低介电常数、低介电损耗角正切、且具有超过200℃的高玻璃化转变温度、处理性也优异的固化性树脂组合物、固化物等。
具体实施方式
以下,针对本发明的实施方式进行说明。需要说明的是,以下的实施方式是用于说明本发明的例示,本发明不仅仅限定于该实施方式。
本实施方式的氰酸酯化合物的制法没有特别限定,例如是将酚改性二甲苯甲醛树脂进行氰酸酯化而得到的氰酸酯化合物。通过这样地将酚改性二甲苯甲醛树脂进行氰酸酯化,能够得到阻燃性优异、固化性高、且固化物的玻璃化转变温度高的氰酸酯化合物。
成为本实施方式的氰酸酯化合物的原料的酚改性二甲苯甲醛树脂是对二甲苯甲醛树脂进行酚改性而成的。此处,二甲苯甲醛树脂是指使(间)二甲苯在酸性催化剂下与甲醛反应而得到的芳香族烃甲醛树脂。另外,本说明书中,酚改性是指使用酚类(具有酚羟基的化合物)进行改性。
二甲苯甲醛树脂的酚改性可以按照本领域公知的方法来进行,其方法没有特别限定。例如,通过使二甲苯甲醛树脂与酚类在酸性催化剂的存在下发生反应,可以得到酚改性二甲苯甲醛树脂。作为酸性催化剂,例如可适合地使用硫酸、盐酸、磷酸等无机酸;草酸、丙二酸、琥珀酸、己二酸、癸二酸、柠檬酸、富马酸、马来酸、甲酸、对甲苯磺酸、甲磺酸、三氟乙酸、二氯乙酸、三氯乙酸、三氟甲磺酸、苯磺酸、萘磺酸、萘二磺酸等有机酸;氯化锌、氯化铝、氯化铁、三氟化硼等路易斯酸;或硅钨酸、磷钨酸、硅钼酸或磷钼酸等固体酸等。另外,反应温度通常优选为50℃~200℃。反应结束后,按照常规方法进行酸性催化剂的中和、利用甲基乙基酮或间二甲苯等有机溶剂的稀释、水洗、提取、蒸馏、未反应酚类的蒸馏去除等,从而能够回收目标物。
上述酚改性中使用的酚类只要是具有酚羟基的化合物(通常是苯环等的芳香环上键合有羟基的化合物)就没有特别限定。例如,可优选使用下述通式(1)所示的酚类。
(式中,Ar表示芳香环,R表示芳香环上的所有氢原子或一价的取代基,一价的取代基为烷基或芳基,芳香环上多个存在的R彼此可以相同也可以不同,其中,R中的至少一个为氢原子。)
上述通式(1)中,作为芳香环,可例示出苯环、萘环、蒽环等,并不特别限定于这些。另外,作为R的烷基,可例示出碳原子数1~8的直链状或分枝状的烷基;更优选为碳原子数1~4的直链状或分枝状的烷基,例如甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基等,并不特别限定于这些。进而,作为R的芳基,可例示出苯基、对甲苯基、萘基、蒽基等,并不特别限定于这些。这些之中,优选的是,下述通式(1)所示的酚类中Ar为苯环且R为0~3个的烷基、以及、Ar为苯环且R为0~2个的芳基。
作为上述通式(1)所示的酚的具体例子,例如可列举出苯酚、2,6-二甲酚、萘酚、联苯酚等,这些之中,从处理的观点出发,优选为苯酚和2,6-二甲酚。
反应后得到的酚改性二甲苯甲醛树脂的主产物是:甲醛在反应时变成亚甲基,二甲苯和酚类的芳香环(例如苯环)彼此介由该亚甲基进行键合而成的物质。需要说明的是,由于甲醛键合于二甲苯以及酚类的芳香环上的位置、酚类的键合位置、聚合数量等不一致,因此反应后得到的酚改性二甲苯甲醛树脂以多种化合物的混合物的形式而得到。
例如,使二甲苯、福尔马林水溶液、2,6-二甲酚以及浓硫酸在氮气气流中回流7小时的水溶剂后,将酸中和,用有机溶剂提取而得到的酚改性二甲苯甲醛树脂成为以下述式(2)~(5)所示的化合物作为代表组成的混合物。
这些之中,上述式(5)之类的结构中不具有羟基的芳香族烃化合物由于无法进行氰酸酯化,因此优选在事前进行蒸馏分离等而去除。
从进一步提高处理性、同时进一步提高所得固化性树脂组合物和固化物的介电常数、介电损耗角正切、阻燃性和耐热性等物性的观点出发,酚改性二甲苯甲醛树脂基于JISK1557-1求出的OH值优选为150~400mgKOH/g、更优选为200~350mgKOH/g。
需要说明的是,酚改性二甲苯甲醛树脂也可以使用市售品。作为市售品,例如可适合地使用Fudow Co.,Ltd.制造的NIKANOL GL16、NIKANOL G等。
本实施方式的氰酸酯化合物可以通过将上述酚改性二甲苯甲醛树脂所具有的羟基进行氰酸酯化而得到。其合成方法没有特别限定,可以适用公知的方法。
例如,通过IAN HAMERTON,“Chemistry and Technology of Cyanate EsterResins”,BLACKIE ACADEMIC&PROFESSIONAL中记载的方法,将酚进行氰酸酯化,可以获得氰酸酯化合物。另外,已知有如下方法:在溶剂中在碱的存在下以卤化氰总是相对于碱过量存在的方式发生反应的方法(美国专利第3553244号);使用叔胺作为碱,相对于卤化氰过量使用该叔胺来合成的方法(日本特开平7-53497号公报);用连续活塞流方式使三烷基胺与卤化氰反应的方法(日本特表2000-501138号公报);用阳离子和阴离子交换对处理由在叔胺的存在下在非水溶液中使酚与卤化氰反应时副产的卤化叔铵的方法(日本特表2001-504835号公报);在可与水分液的溶剂的存在下同时添加叔胺和卤化氰使酚化合物反应后,水洗分液,使用仲醇或叔醇类或烃的不良溶剂从所得溶液中沉淀精制的方法(日本专利第2991054号);以及,在水与有机溶剂的二相系溶剂中在酸性条件下使萘酚类、卤化氰和叔胺反应的方法(日本特开2007-277102号公报)等,可以适合地使用这些公知的方法获得本实施方式的氰酸酯化合物。需要说明的是,所得氰酸酯化合物可以通过NMR等公知的方法进行鉴定。
若具体地进行例示,则通过使通式(2)~(4)所示的2,6-二甲酚改性二甲苯甲醛树脂与氯化氰在溶剂中在碱性化合物的存在下发生反应,可以得到以通式(6)~(8)所示的化合物作为代表组成的氰酸酯(混合物)。
在上述的氰酸酯化合物之中,从固化性和耐燃性的观点出发,优选为下述式(I)所示的氰酸酯化合物。
(式中,R1各自独立地表示亚甲基、亚甲基氧基、亚甲基氧基亚甲基或氧基亚甲基;R2~R4各自独立地表示氢原子、碳原子数为1~3的烷基(优选为甲基)、羟基或羟基亚甲基;T1表示氢原子、羟基或羟基亚甲基;x各自独立地表示0~4的整数(优选为0~2的整数);y和z各自独立地表示0~3的整数(优选为0~2的整数);w表示0或1的整数;m表示0以上的整数;n1和n2各自独立地表示1以上的整数。)
上述式(I)中,m、n1以及n2表示各结构单元的比率,各重复单元的排列不限。即,式(I)的化合物可以是无规共聚物,也可以是嵌段共聚物(在本说明书中,各结构单元的比率均相同。)。另外,式(I)的化合物也可以通过2个以上R1进行桥接/连结。需要说明的是,m的上限值通常为50以下、优选为20以下,n1和n2的上限值通常为20以下。
本实施方式的氰酸酯化合物的重均分子量Mw没有特别限定,优选为250~10,000、更优选为300~5,000。
接着,针对本实施方式的固化性树脂组合物进行说明。
本实施方式的固化性树脂组合物包含上述的氰酸酯化合物。该固化性树脂组合物在不损害所期望的特性的范围内可以含有除上述氰酸酯化合物以外的氰酸酯化合物(以下称为“其它氰酸酯化合物”。)、环氧树脂、氧杂环丁烷树脂、和/或具有可聚合的不饱和基团的化合物等。
作为其它氰酸酯化合物,可以使用通常公知的氰酸酯化合物,没有特别限定,例如可列举出双酚A二氰酸酯、双酚F二氰酸酯、双酚M二氰酸酯、双酚P二氰酸酯、双酚E二氰酸酯、苯酚酚醛清漆型氰酸酯、甲酚酚醛清漆型氰酸酯、双环戊二烯酚醛清漆型氰酸酯、四甲基双酚F二氰酸酯、联苯酚二氰酸酯等。这些氰酸酯化合物可以单独使用1种,或者混合两种以上使用。
作为环氧树脂,可以使用通常公知的环氧树脂,没有特别限定,例如可列举出双酚A型环氧树脂、双酚E型环氧树脂、双酚F型环氧树脂、双酚S型环氧树脂、双酚A酚醛清漆型环氧树脂、联苯型环氧树脂、苯酚酚醛清漆型环氧树脂、甲酚酚醛清漆型环氧树脂、二甲苯酚醛清漆型环氧树脂、萘型环氧树脂、蒽型环氧树脂、3官能苯酚型环氧树脂、4官能苯酚型环氧树脂、三缩水甘油基异氰脲酸酯、缩水甘油酯型环氧树脂、脂环式环氧树脂、双环戊二烯酚醛清漆型环氧树脂、联苯酚醛清漆型环氧树脂、苯酚芳烷基酚醛清漆型环氧树脂、萘酚芳烷基酚醛清漆型环氧树脂、芳烷基酚醛清漆型环氧树脂、联苯芳烷基型环氧树脂、萘酚芳烷基型环氧树脂、双环戊二烯型环氧树脂、多元醇型环氧树脂、脂环式环氧树脂、或者它们的卤化物等。这些环氧树脂可以单独使用1种,或者混合两种以上使用。
作为氧杂环丁烷树脂,可以使用通常公知的氧杂环丁烷树脂,没有特别限定,例如可列举出氧杂环丁烷、2-甲基氧杂环丁烷、2,2-二甲基氧杂环丁烷、3-甲基氧杂环丁烷、3,3-二甲基氧杂环丁烷等烷基氧杂环丁烷;3-甲基-3-甲氧基甲基氧杂环丁烷、3,3’-二(三氟甲基)全氟氧杂环丁烷、2-氯甲基氧杂环丁烷、3,3-双(氯甲基)氧杂环丁烷、OXT-101(东亚合成株式会社制,商品名)、OXT-121(东亚合成株式会社制,商品名)等。这些氧杂环丁烷树脂可以单独使用1种,或者混合两种以上使用。
需要说明的是,在固化性树脂组合物中使用环氧树脂和/或氧杂环丁烷树脂时,根据需要,也可以使用环氧树脂固化剂和/或氧杂环丁烷树脂固化剂。作为环氧树脂固化剂,可以使用通常公知的环氧树脂固化剂,没有特别限定,例如可列举出2-甲基咪唑、2-乙基-4-甲基咪唑、2-苯基咪唑、1-氰基乙基-2-苯基咪唑、1-氰基乙基-2-乙基-4-甲基咪唑、2-苯基-4,5-二羟基甲基咪唑、2-苯基-4-甲基-5-羟基甲基咪唑等咪唑衍生物;双氰胺、苄基二甲胺、4-甲基-N,N-二甲基苄胺等胺化合物;磷化氢系或磷鎓系的磷化合物等。另外,作为氧杂环丁烷树脂固化剂,可以使用通常公知的氧杂环丁烷树脂固化剂,没有特别限定,可列举出阳离子聚合引发剂。作为阳离子聚合引发剂,例如可列举出市售的San-Aid SI60L、San-Aid SI-80L、San-Aid SI100L(三新化学工业株式会社制);CI-2064(日本曹达株式会社制);Irgacure261(Ciba SpecialtyChemicals制);Adekaoptomer SP-170、Adekaoptomer SP-150(ADEKACorporation制);CYRACURE UVI-6990(UCC公司制)等。另外,阳离子聚合引发剂也可以用作环氧树脂固化剂。这些固化剂可以单独使用1种,或者组合两种以上使用。
作为具有可聚合的不饱和基团的化合物,可以使用通常公知的化合物,没有特别限定,例如可列举出乙烯、丙烯、苯乙烯、二乙烯基苯、二乙烯基联苯等乙烯基化合物;(甲基)丙烯酸甲酯、(甲基)丙烯酸2-羟基乙酯、(甲基)丙烯酸2-羟基丙酯、聚丙二醇二(甲基)丙烯酸酯、三羟甲基丙烷二(甲基)丙烯酸酯、三羟甲基丙烷三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯等1元醇或多元醇的(甲基)丙烯酸酯类;双酚A型环氧(甲基)丙烯酸酯、双酚F型环氧(甲基)丙烯酸酯等环氧(甲基)丙烯酸酯类;苯并环丁烯树脂、(双)马来酰亚胺树脂等。这些具有不饱和基的化合物可以单独使用1种,或者混合两种以上使用。
需要说明的是,在使用具有可聚合的不饱和基团的化合物的情况下,也可以根据需要使用公知的聚合引发剂。作为聚合引发剂,可以使用通常公知的聚合引发剂,没有特别限定,例如可列举出过氧化苯甲酰、对氯过氧化苯甲酰、二叔丁基过氧化物、过氧化碳酸二异丙酯、过氧化碳酸二-2-乙基己酯等过氧化物、或偶氮二异丁腈等偶氮化合物等。这些聚合引发剂可以单独使用1种,或者组合两种以上使用。
进而,本实施方式的固化性树脂组合物还可以根据需要含有热塑性树脂、无机填充材料、固化催化剂、固化促进剂、着色颜料、消泡剂、表面调节剂、阻燃剂、紫外线吸收剂、抗氧化剂、光聚合引发剂、荧光增白剂、光敏剂、染料、颜料、增稠剂、润滑剂、流动调节剂、分散剂、流平剂、光泽剂、阻聚剂、硅烷偶联剂等公知的添加剂。另外,也可以根据需要含有溶剂。这些任意的添加剂可以单独使用1种,或者组合两种以上使用。
作为无机填充材料,可以使用通常公知的无机填充材料,没有特别限定,例如可列举出天然二氧化硅、合成二氧化硅、熔融二氧化硅、无定形二氧化硅、中空二氧化硅等二氧化硅类;勃姆石、氧化钼、钼酸锌等钼化合物;白炭黑、钛白、AEROSIL、有机硅复合粉末、有机硅树脂粉末、硼酸锌、锡酸锌、氧化铝、滑石、天然云母、合成云母、高岭土、粘土、煅烧粘土、煅烧高岭土、煅烧滑石、氧化锌、氧化镁、氧化锆、氢氧化铝、氮化硼、硫酸钡、E-玻璃、A-玻璃、NE-玻璃、C-玻璃、L-玻璃、D-玻璃、S-玻璃、M-玻璃G20、玻璃短纤维(包含E玻璃、T玻璃、D玻璃、S玻璃、Q玻璃等玻璃微粉末类。)、中空玻璃、球状玻璃等。这些无机填充材料可以单独使用1种,或者组合两种以上使用。
另外,作为固化催化剂,可以使用通常公知的固化催化剂,没有特别限定,例如可列举出辛酸锌、环烷酸锌、环烷酸钴、环烷酸铜、乙酰丙酮铁等金属盐;苯酚、醇、胺等具有活性羟基的化合物等。这些固化催化剂可以单独使用1种,或者组合两种以上使用。
作为溶剂,可以使用通常公知的溶剂,没有特别限定,可列举出丙酮、甲基乙基酮、甲基异丁基酮、环己酮等酮系溶剂;丙二醇单甲醚、丙二醇单甲醚乙酸酯等溶纤剂系溶剂;乳酸乙酯、乙酸甲酯、乙酸乙酯、乙酸丁酯、乙酸异戊酯、乳酸乙酯、甲氧基丙酸甲酯、羟基异丁酸甲酯等酯系溶剂;甲醇、乙醇、异丙醇、1-乙氧基-2-丙醇等醇系溶剂;甲苯、二甲苯、苯甲醚等芳香族系烃等,并不特别限定于这些。这些溶剂可以单独使用1种,或者组合两种以上使用。
通过使上述固化性树脂组合物固化,可以得到本实施方式的固化物。其固化方法没有特别限定,例如通过热、光等可以使上述固化性树脂组合物发生固化。另外,例如使上述固化性树脂组合物熔融或使其在溶剂中溶解之后,流入到模具内,在通常的条件下使其固化,从而可以得到期望形状的固化物。需要说明的是,进行热固化时的处理温度没有特别限定,从促进固化反应和抑制得到的固化物的性能劣化的观点出发,优选在120~300℃的范围内。
<固化性树脂组合物的用途>
通过将上述固化性树脂组合物浸渗或涂布于基材并进行干燥,可以制造预浸料。作为此处使用的基材,可以使用通常公知的基材,例如无机纤维基材、有机纤维基材等,没有特别限定。
作为前述基材,没有特别限定,例如可列举出玻璃织布、玻璃无纺布等玻璃纤维基材;石英等玻璃以外的无机纤维基材;以聚酰亚胺树脂纤维、聚酰胺树脂纤维、芳香族聚酰胺树脂纤维、全芳香族聚酰胺树脂纤维等聚酰胺系树脂纤维、聚酯树脂纤维、芳香族聚酯树脂纤维、全芳香族聚酯树脂纤维等聚酯系树脂纤维、聚酰亚胺树脂纤维、氟树脂纤维等作为主成分的织布或无纺布所构成的合成纤维基材;以牛皮纸、棉籽绒纸、籽绒与牛皮纸浆的混抄纸等作为主成分的纸基材等有机纤维基材等。可以根据预浸料所要求的性能、例如强度、吸水率、热膨胀系数等适当选择这些公知的基材并使用。
作为构成前述玻璃纤维基材的玻璃,没有特别限定,例如可列举出E玻璃、D玻璃、C玻璃、A玻璃、S玻璃、D玻璃、Q玻璃、NE玻璃、T玻璃、H玻璃等。
制造前述预浸料的方法可以适当适用通常公知的方法,没有特别限定。例如可以适用如下方法来制造预浸料,所述方法为:使用前述固化性树脂组合物制备树脂清漆,并将基材浸渍在树脂清漆中的方法;利用各种涂布机进行涂布的方法;通过喷雾进行吹附的方法等。这些之中,优选将基材浸渍在树脂清漆中的方法。由此,可以提高树脂组合物相对于基材的浸渗性。需要说明的是,将基材浸渍于树脂清漆时,可以使用通常的浸渗涂布设备。例如,可以适用使树脂组合物清漆浸渗到无机和/或有机纤维基材中,进行干燥,B阶化,从而制造预浸料的方法等。
另外,本实施方式的固化性树脂组合物也可以用于覆金属层压板和多层板用途。这些层压板等的制造方法可以适用通常公知的方法,没有特别限定。例如,将上述预浸料与金属箔进行层叠,通过加热加压成型而得到层压板。此时,加热温度没有特别限定,通常优选为65~300℃、更优选为120~270℃。另外,加压压力没有特别限定,通常优选为2~5MPa、更优选为2.5~4MPa。
进而,使用上述固化性树脂组合物,可以制造密封材料。密封材料的制造方法可以适用通常公知的方法,没有特别限定。例如,通过使用公知的混合机将上述固化性树脂组合物以及密封材料用途的各种公知的添加剂或溶剂等混合,可以制造密封材料。需要说明的是,混合时的氰酸酯化合物、各种添加剂、溶剂的添加方法可以适用通常公知的氰酸酯化合物、各种添加剂、溶剂的添加方法,没有特别限定。
另外,可以使用上述固化性树脂组合物来制造纤维强化复合材料。纤维强化复合材料的制造方法可以适用通常公知的方法,没有特别限定。例如,通过将上述固化性树脂组合物与强化纤维进行复合化(一体化),可以制造纤维强化复合材料。
作为强化纤维,没有特别限定,例如可以使用碳纤维、玻璃纤维、芳纶纤维、硼纤维、PBO纤维、高强力聚乙烯纤维、氧化铝纤维以及碳化硅纤维等纤维。针对强化纤维的形态、排列,没有特别限定,可以从织物、无纺布、闷光织物(mat)、针织物、线绳、单向线料、粗纱、短切纤维等中适当选择。另外,作为强化纤维的形态,例如还可以适用预成型体(由强化纤维构成的织物基布的层叠物、或者用缝纫线将该织物基布缝合一体化而获得的材料、或者立体织物/编织物等纤维结构物)。作为纤维强化复合材料的更具体的制造方法,例如可列举出复合材料液体模塑成型(liquid composite molding)法、树脂膜熔渗(resin film infusion)法、长纤维卷绕(filament winding)法、手糊(hand lay-up)法、拉挤成型(pultrusion)法等。这些之中,作为复合材料液体模塑成型法之一的树脂传递成型法由于可以将金属板、泡沫芯(foamcore)、蜂窝芯(honeycomb core)等除了预成型体以外的原材料预先设置在成型模具内,可以应对各种用途,因此在短时间内大量生产形状比较复杂的复合材料时优选使用。
另外,可以使用上述固化性树脂组合物来制造粘接剂。粘接剂的制造方法可以适用通常公知的方法,没有特别限定。例如,通过使用公知的混合机将上述固化性树脂组合物与粘接剂用途的各种公知的添加剂或溶剂等混合,可以制造粘接剂。需要说明的是,混合时的氰酸酯化合物、各种添加剂、溶剂的添加方法可以适用通常公知的氰酸酯化合物、各种添加剂、溶剂的添加方法,没有特别限定。
本实施方式的固化性树脂组合物的处理性优异,进而能够实现介电常数和介电损耗角正切低、且具有优异的阻燃性和耐热性的固化物,因此能够在要求这些性能的广泛用途中使用,其用途不限定于上述用途。即,本实施方式的固化性树脂组合物除了上述物性以外,例如能够实现具有优异低热膨胀性和低吸水性的固化物,因此作为高功能性高分子材料是极其有用的,作为热物性、电气物性以及机械物性优异的材料而可以在广大用途中使用。
实施例
以下,示出合成例、实施例以及比较例来进一步详细说明本发明,但本发明不限定于这些例子。需要说明的是,以下,在无特别说明的情况下,“份”表示“质量份”。
(实施例1)
2,6-二甲酚改性二甲苯甲醛树脂的氰酸酯(下述式(Ia)的氰酸酯(作
为代表组成而具有下述式(9)):简称为NXDC)的合成
(式中,R1、T1、w、m、n1以及n2与上述式(I)中说明的意义相同。)
<2,6-二甲酚改性二甲苯甲醛树脂的合成>
投入2,6-二甲酚486.8g(3.99mol)和催化剂PTSA(对甲苯磺酸)6.3g并搅拌升温,在液体温度达到125℃的时刻,花费1小时滴加二甲苯甲醛树脂(NIKANOL GL16、Fudow Co.,Ltd.制)144g。滴加过程中持续进行升温,以150℃、3小时使反应完结。反应后冷却至120℃以下,向反应液中添加间二甲苯160g,接着添加甲基异丁基酮240g,将反应液稀释。接着,将稀释的反应液用70~80℃的温水400g重复洗涤3次。
接着,通过蒸馏操作进行脱溶剂和未反应的2,6-二甲酚的蒸馏去除,得到下述式(Ia’)所示的2,6-二甲酚改性二甲苯甲醛树脂的粗制品362g。
(式中,R1、T1以及w与上述式(I)中说明的意义相同,n与上述式(I)中说明的n2意义相同。)
将向所得粗制品292g中添加间二甲苯300g而成的混合物置于热水浴上进行搅拌溶解(残留部分结晶),边持续搅拌边用冰水进行冷却,使结晶析出,其后利用G-3过滤器进行过滤操作,从而去除结晶。进而,通过蒸馏操作从滤液中蒸馏去除溶剂,得到2,6-二甲酚改性二甲苯甲醛树脂的精制品175g。
基于JISK1557-1求出所得2,6-二甲酚改性二甲苯甲醛树脂的OH值,结果为318mgKOH/g。
<2,6二甲酚改性二甲苯甲醛树脂的氰酸酯化物(NXDC)的合成>
将利用上述方法得到的式(Ia’)所示的2,6-二甲酚改性二甲苯甲醛树脂的精制品256g(以OH基计为1.45mol)以及1.6mol三乙胺溶解在3-甲基四氢呋喃600mL中(溶液1)。其后,花费1.5小时以-10℃向2.8mol氯化氰的二氯甲烷溶液500g中滴加溶液1。搅拌30分钟后,滴加0.8mol三乙胺与二氯甲烷115g的混合溶液,进而搅拌30分钟,使反应完结。并且,从反应液滤除三乙胺的盐酸盐,将所得滤液用0.1N盐酸1,000mL洗涤后,进而用NaCl水溶液1,000mL洗涤3次,最后用水1,000mL进行洗涤。将二氯甲烷溶液利用硫酸钠进行干燥,利用蒸馏操作蒸馏去除溶剂,从而得到目标物即上述式(Ia)所示的2,6-二甲酚改性二甲苯甲醛树脂的氰酸酯(NXDC)240g的罂粟红(poppy red)色粘性物。
该化合物在25℃时相对于甲基乙基酮能够溶解30质量%以上。另外,使用TA Instruments.Japan制造的流变仪AR2000EX测定粘度时,该化合物的粘度在100℃时为0.3Pa·s。利用GPC进行测定时,该化合物的重均分子量(Mw)为650。
(实施例2)
固化性树脂组合物的制备和固化物的制作
将实施例1中得到的氰酸酯NXDC100质量份投入到茄型烧瓶中,以150℃使其加热熔融,用真空泵进行脱气。其后,通过添加辛酸锌0.05质量份并使其振荡1分钟而混合,从而制备固化性树脂组合物。
使所得固化性树脂组合物流入使用玻璃板(120mm×120mm×5mmt)、聚酰亚胺薄膜(Kapton200H:DU PONT-TORAY CO.,LTD.)、氟橡胶制O型环(S-100:MORISEI KAKO Co.,Ltd.)制作的模具中,使用烘箱在170℃下加热1小时、其后进一步在230℃下加热9小时而使其固化,对固化物进行浇铸成型。冷却后,通过研磨而去除聚酰亚胺薄膜,取出固化物。
通过以下方法评价固化物的特性。
玻璃化转变温度(Tg):通过动态粘弹性测定(DMA)而求出。以10GHz的振动频率进行测定。
介电常数、介电损耗角正切:使用Agilent Technologies制造的HP8722ES,利用谐振腔微扰法(cavity perturbation method)而求出。
阻燃性:基于UL94进行耐燃性试验。需要说明的是,样品大小为10mm×70mm×1.5mm。
将评价结果示于表1。
(实施例3)
苯酚改性二甲苯甲醛树脂的氰酸酯(下述式(Ib)的氰酸酯(作为代表
组成而具有下述式(10)):简称为GLPC)的合成
(式中,R1、T1、w、m、n1以及n2与上述式(I)中说明的意义相同。)
<苯酚改性二甲苯甲醛树脂的合成>
投入苯酚800g(8.5mol)和催化剂PTSA(对甲苯磺酸)0.43g并搅拌升温,在液体温度130℃下花费1小时滴加二甲苯甲醛树脂(NIKANOL G、FudowCo.,Ltd.制)670g。在滴加过程中,回流温度从150℃降低至105℃。滴加后用1小时使反应完结。反应后,为了脱苯酚而以170℃实施了2.5小时的水蒸汽蒸馏。其后,边冷却边缓慢地添加甲基异丁基酮1700g来进行稀释。接着,将稀释了的反应液用70~80℃的温水850g重复洗涤3次。
接着,通过蒸馏操作进行脱溶剂和微量苯酚的蒸馏去除,得到下述式(Ib’)所示的苯酚改性二甲苯甲醛树脂1130g。
基于JISK1557-1求出所得苯酚改性二甲苯甲醛树脂的OH值,结果为314mgKOH/g。
(式中,R1、T1以及w与上述式(I)中说明的意义相同,n与上述式(I)中说明的n2的意义相同。)
<苯酚改性二甲苯甲醛树脂的氰酸酯(GLPC)的合成>
将利用上述方法得到的式(Ib’)所示的苯酚改性二甲苯甲醛树脂20g(以OH基计为0.112mol)以及三乙胺17.13g(0.168mol)溶解在二氯甲烷120g中(溶液2)。以-5~+5℃花费10分钟向0.249mol氯化氰的二氯甲烷溶液48.1g、36%盐酸23.76g(0.235mol)以及水147.3g经搅拌混合而成的溶液中滴加溶液2。搅拌30分钟后,滴加三乙胺11.42g(0.112mol)与二氯甲烷11.4g的混合溶液,进而搅拌30分钟而使反应完结。将反应液进行分液,萃取有机相。将所得有机相用水100g洗涤4次后,通过蒸馏将二氯甲烷蒸馏去除,得到目标物即上述式(Ib)所示的苯酚改性二甲苯甲醛树脂的氰酸酯(GLPC)23.1g的罂粟红色粘性物。
该化合物在25℃时相对于甲基乙基酮能够溶解30质量%以上。另外,使用TA Instruments.Japan制造的流变仪AR2000EX测定粘度时,该化合物的粘度在100℃时为0.4Pa·s。
利用GPC进行测定时,该化合物的重均分子量(Mw)为1050。
(实施例4)
除了使用实施例3中得到的GLPC来代替NXDC以外,与实施例2同样地进行,制备固化性树脂组合物,制作固化物。
将所得固化物的物性的评价结果示于表1。
(比较例1)
除了单独使用双酚A二氰酸酯skylex(三菱瓦斯化学株式会社制)来代替NXDC以外,与实施例2同样地进行,制备固化性树脂组合物,制作固化物。
需要说明的是,上述的双酚A二氰酸酯skylex在25℃时相对于甲基乙基酮能够溶解30质量%以上。另外,使用TA Instruments.Japan制造的流变仪AR2000EX测定粘度时,其粘度在100℃时为0.02Pa·s。
将所得固化物的物性的评价结果示于表1。
(比较例2)
除了使用苯酚酚醛清漆氰酸酯PT30(LONZA Japan.制)来代替NXDC以外,与实施例2同样地进行,制备固化性树脂组合物,制作固化物。
需要说明的是,上述苯酚酚醛清漆氰酸酯PT30在25℃时相对于甲基乙基酮能够溶解30质量%以上。另外,使用TA Instruments.Japan制造的流变仪AR2000EX测定粘度时,其粘度在100℃时为0.5Pa·s。
将所得固化物的物性的评价结果示于表1。
[表1]
如表1所明确那样,可确认:与使用了以往的氰酸酯化物的固化性树脂组合物的固化物相比,使用了本发明的酚改性二甲苯甲醛树脂的氰酸酯化物的固化性树脂组合物的固化物的介电常数和介电损耗角正切低、具有优异的阻燃性。而且,可确认:这些固化物与以往制品同样地均具有超过200℃的高玻璃化转变温度,具有优异的耐热性。另外,可确认:本发明的酚改性二甲苯甲醛树脂的氰酸酯化物的粘度低且具有优异的溶剂溶解性,处理性也优异。
需要说明的是,本申请基于2011年8月9日向日本特许厅申请的日本专利申请(特愿2011-174070号)要求优先权,将其内容作为参照援引至此。
产业上的可利用性
如上所述,本发明不仅处理性优异、能够实现介电常数和介电损耗角正切低、且具有优异的阻燃性和耐热性的固化物,还能够实现具有优异的低热膨胀性和低吸水性的固化物,因此能够在要求这些性能的各种用途中广泛且有效地利用。例如,能够在电绝缘材料、密封材料、粘接剂、层压材料、抗蚀层(resist)、积层层压板材料、以及土木/建筑、电气/电子、汽车、铁道、船舶、飞机、体育用品、美术/工艺等领域中的固定材料、结构部件、增强剂、印模材料等领域中有效地利用,尤其是能够在要求浇铸性、低热膨胀性、耐燃性、高机械强度的电绝缘材料或半导体密封材料、电子部件的粘接剂、飞机结构部件、卫星结构部材以及铁路车辆结构部件等中特别有效地利用。
Claims (14)
1.一种氰酸酯化合物,其是将酚改性二甲苯甲醛树脂进行氰酸酯化而得到的。
2.根据权利要求1所述的氰酸酯化合物,其具有下述通式(I)所示的结构,
式(I)中,R1各自独立地表示亚甲基、亚甲基氧基、亚甲基氧基亚甲基或氧基亚甲基;R2~R4各自独立地表示氢原子、碳原子数为1~3的烷基、羟基或羟基亚甲基;T1表示氢原子、羟基或羟基亚甲基;x各自独立地表示0~4的整数;y和z各自独立地表示0~3的整数;w表示0或1的整数;m表示0以上的整数;n1和n2各自独立地表示1以上的整数。
3.根据权利要求1所述的氰酸酯化合物,其中,所述酚改性二甲苯甲醛树脂是用下述通式(1)所示的酚类将二甲苯甲醛树脂进行改性而成的,
式(1)中,Ar表示芳香环,R表示芳香环上的所有氢原子或一价的取代基,一价的取代基为烷基或芳基,芳香环上多个存在的R彼此可以相同也可以不同,其中,R中的至少一个为氢原子。
4.根据权利要求3所述的氰酸酯化合物,其中,所述通式(1)所示的酚类为苯酚和/或2,6-二甲酚。
5.根据权利要求1所述的氰酸酯化合物,其中,重均分子量Mw为250~10,000。
6.一种权利要求1~5中任一项所述的氰酸酯化合物的制造方法,其具有:
将二甲苯甲醛树脂进行酚改性的工序;以及
将所得酚改性二甲苯甲醛树脂所具有的酚羟基进行氰酸酯化的工序。
7.一种固化性树脂组合物,其包含权利要求1~5中任一项所述的氰酸酯化合物。
8.根据权利要求7所述的固化性树脂组合物,其还包含选自由权利要求1~5中任一项所述的氰酸酯化合物以外的氰酸酯化合物、环氧树脂、氧杂环丁烷树脂以及具有可聚合的不饱和基团的化合物组成的组中的至少1种以上。
9.一种固化物,其是使权利要求7所述的固化性树脂组合物进行固化而成的。
10.一种预浸料,其是将权利要求7所述的固化性树脂组合物浸渗或涂布于基材并使其干燥而成的。
11.一种层压板,其是在权利要求10所述的预浸料上层叠金属箔并加热加压成型而成的。
12.一种密封用材料,其包含权利要求7所述的固化性树脂组合物。
13.一种纤维强化复合材料,其包含权利要求7所述的固化性树脂组合物。
14.一种粘接剂,其包含权利要求7所述的固化性树脂组合物。
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EP2743283A1 (en) | 2014-06-18 |
TWI547469B (zh) | 2016-09-01 |
JP5950127B2 (ja) | 2016-07-13 |
JPWO2013021869A1 (ja) | 2015-03-05 |
TW201313663A (zh) | 2013-04-01 |
KR101892784B1 (ko) | 2018-08-28 |
KR20140046007A (ko) | 2014-04-17 |
WO2013021869A1 (ja) | 2013-02-14 |
EP2743283A4 (en) | 2015-01-21 |
EP2743283B1 (en) | 2016-05-25 |
US10155835B2 (en) | 2018-12-18 |
US20140308530A1 (en) | 2014-10-16 |
CN103732642A (zh) | 2014-04-16 |
WO2013021869A9 (ja) | 2013-05-30 |
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