CN102574987A - 无溶剂一液型氰酸酯-环氧复合树脂组合物 - Google Patents
无溶剂一液型氰酸酯-环氧复合树脂组合物 Download PDFInfo
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- CN102574987A CN102574987A CN201080042790XA CN201080042790A CN102574987A CN 102574987 A CN102574987 A CN 102574987A CN 201080042790X A CN201080042790X A CN 201080042790XA CN 201080042790 A CN201080042790 A CN 201080042790A CN 102574987 A CN102574987 A CN 102574987A
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- epoxy resin
- cyanate
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Abstract
本发明为一种无溶剂一液型氰酸酯—环氧树脂组合物,其具有优良的储存稳定性及硬化性,且同时具有高耐热性,其特征在于,包含:(A)氰酸酯、(B)环氧树脂、(C)胍化合物、及(D)由下述通式所示的酚化合物的群中选择的至少一种酚化合物。其中,通式中的l为0至4的整数,R1表示非取代或由氟取代的1价烃基。
Description
技术领域
本发明有关一种氰酸酯—环氧复合树脂组合物,特别为含有氰酸酯、环氧树脂、胍化合物、及联苯化合物,并具有优良的储存稳定性、低温硬化性、及耐热性的无溶剂一液型氰酸酯—环氧复合树脂组合物。
背景技术
目前,环氧树脂组合物因具有优良的电气性能及粘结力,因而被使用在电气/电子范畴的各种用途上。
同时,现有的环氧树脂在单独或混合使用仍未能获得充分的结果时,多使用以环氧树脂与氰酸酯混合制成的氰酸酯—环氧复合树脂组合物,作为要求高耐热性的半导体封装及成形的用途等使用的树脂组合物。
例如已往已有提案揭示以氰酸酯、环氧树脂、双氰二胺等制成的树脂组合物(参考专利文献1),但具有需进行硬化,因而需要高温及长时间操作的缺点,未能得到可充分满足的特性。
现有技术文献
专利文献
专利文献1:日本特开平10-130465号公报
发明内容
发明要解决的技术问题
因此,本发明的第1目的在于提供一种无溶剂一液型氰酸酯—环氧树脂组合物,其由氰酸酯与环氧树脂组合制成,具有优良的储存稳定性及硬化性,且同时具有高耐热性。
本发明的第2目的在于提供一种无溶剂一液型氰酸酯—环氧树脂组合物,其适于半导体封装及成形的用途等,而具有优良的储存稳定性。
本发明的第3目的在于提供一种无溶剂一液型氰酸酯—环氧复合树脂组合物,其适于作为粘结剂组合物,而具有优良的储存稳定性、低温硬化性、及耐热性。
解决问题的技术方案
本发明人等为达成上述各目的,通过反复深入研究,结果发现在具有氰酸酯、环氧树脂、及胍化合物,并同时含有特定的酚化合物时,可得到良好的结果,而完成本发明。
也即,本发明为一种无溶剂一液型氰酸酯—环氧复合树脂组合物,包含:(A)氰酸酯、(B)环氧树脂、(C)胍化合物、及(D)由下述通式所示的酚化合物的群中选择的至少一种酚化合物,以及以该组合物经硬化制成的硬化物、及以前述树脂组合物制成的封装用材料或粘结剂。
通式:
其中,上述通式中所示的l为0至4的整数,R1为非取代或由氟取代的1价烃基。
本发明中前述(C)成分的胍化合物优选为以由下述通式所示的化合物的群中选择的至少一种,特别优选由乙酰胍胺(acetoguanamine)、苯胍胺(benzoguanamine)、双氰二胺(dicyandiamide)之中选择的至少一种。
通式:
其中,上述通式中的m表示1至5的整数,R1′表示胺基、或非取代或由氟取代的碳原子数1至15的1价烃基,R2表示氢原子、或碳原子数1至4的烷基。
并且,本发明中前述(D)成分的酚化合物优先4,4′-联苯酚及/或3,3′,5,5′-四甲基-4,4′-联苯酚,前述(A)的氰酸酯优选由下述通式(1)、通式(2)及它们的预聚合物的群中选择的至少一种。
通式(1):
N≡C-O-R2’-R1”-R3-O-C≡N
其中,上述通式(1)中的R1″表示非取代或由氟取代的2价烃基、-O-、-S-、或单键,R2′及R3各自独立,表示非取代或由1至4个烷基取代的伸苯基。
通式(2):
其中,上述通式(2)中的n′为1至100的正数,R表示非取代或由氟取代的2价烃基。R4及R5为氢原子、或碳原子数1至4的烷基。
发明效果
本发明的氰酸酯—环氧树脂组合物,不但储存稳定性优良,且具有优良的低温硬化性、及耐热性,可以使用于例如针对混凝土、水泥砂浆、各种金属、皮革、玻璃、橡胶、塑料、木材、布、纸等的涂料或粘结剂等范围广泛的用途上。尤其因为其具有高耐热性及优良的粘结性,因此也适于使用在半导体保护封装及电子零部件的粘结等电子材料的用途及汽车材料的用途上。
具体实施方通式
以下对本发明的氰酸酯—环氧树脂组合物详细说明。本发明中使用的(A)成分的氰酸酯并无特别限定,但优选使用下述通式(1)或通式(2)所示的化合物、及这些化合物中氰氧基的部分形成三嗪环的预聚合物。
通式(1):
N≡C-O-R2’-R1”-R3-O-C≡N
上述通式中的R1″表示非取代或由氟取代的2价烃基、-O-、-S-、或单键,R2′及R3各自独立,表示非取代或由1至4个烷基取代的伸苯基。
通式(2):
其中,上述通式(2)中的n′为1至100的正数,R表示非取代或由氟取代的2价烃基。R4及R5为氢原子、或碳原子数1至4的烷基。这些化合物中,本发明中特别优选下述化合物。
另外,作为前述预聚合物例如可举出如前述通式(1)所示化合物的全部或部分3聚合化的化合物。
本发明中较佳的氰酸酯为下述通式(3)所示的化合物及它们的预聚合物,特别优选4,4′-亚乙基双伸苯基氰酸酯、2,2-双(4-氰氧苯基)丙烷、及双(4-氰氧-3,5-二甲苯基)甲烷。
通式(3):
上述通式(3)中的R5′可由下述的基中选择。
上述的R6至R11各自独立,为氢原子、或非取代或由氟取代的甲基,n″为4至12的整数。
本发明中,这些氰酸酯可单独使用也可使用2种以上的组合。
作为本发明中使用的(B)成分的环氧树脂例如可举出如氢醌、间苯二酚、邻苯二酚、间苯三酚等单环多元酚化合物的聚环氧丙基醚化合物;二羟萘、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-羟异苯丙基苯)、1,4-双(4-羟异苯丙基苯)、1,1,3-参(4-羟苯基)丁烷、1,1,2,2-肆(4-羟苯基)乙烷、硫双酚、磺双酚、氧双酚、酚醛酚树脂(phenol novolac)、酚醛邻甲酚树脂(orthocresolnovolac)、酚醛乙基酚树脂、酚醛丁基酚树脂、酚醛辛基酚树脂、酚醛间苯二酚树脂(resorcin novolac)、萜烯酚等多环多元酚化合物的聚环氧丙基醚化合物;乙二醇、丙二醇、丁二醇、己二醇、聚乙二醇、硫二乙二醇、丙三醇、三羟甲丙烷(trimethylolpropane)、新戊四醇(pentaerythritol)、山梨醇(sorbitol)、双酚A-环氧乙烷加成物等多元醇类的聚环氧丙基醚;顺丁烯二酸、反丁烯二酸、衣康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚物酸、三聚物酸、苯二甲酸、间苯二甲酸、对苯二甲酸、苯三甲酸、均苯三甲酸、苯四甲酸、四氢苯二甲酸、六氢苯二甲酸、内亚甲四氢苯二甲酸等脂族、芳族、或脂环族多碱酸的环氧丙酯类及甲基丙烯酸环氧丙酯的单独聚合物或共聚物;N,N-二环氧丙基苯胺(N,N-diglycidylaniline)、双(4-(N-甲基-N-环氧丙胺)苯基)甲烷、4-环氧乙烷基甲氧基-苯基)双-环氧乙烷基甲基-胺、(2-甲基-4-环氧乙烷基甲氧基苯基)双-环氧乙烷基甲基-胺、二环氧丙基邻苄胺等含环氧丙基胺基的环氧化合物;二环氧乙烯环己烯、二环氧二环戊二烯、3,4-环氧环己烷羧酸-3,4-环氧环己基甲酯、6-甲基环己烷羧酸-3,4-环氧-6-甲基环己基甲酯、己二酸-双(3,4-环氧-6-甲基环己基甲基)酯等环状烯化合物的环氧化物;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、三聚异氰酸三环氧丙酯等杂环化合物。此外,由这些环氧树脂的末端为三聚异氰酸酯的预聚合物形成内部交联、或其经多元的活性氢化合物(多元酚、聚胺、含羰基化合物、聚磷酸酯等)形成高分子量化的化合物也可使用。
另外,上述聚环氧化合物优选环氧当量70至3000,更优选90至2000。该环氧当量小于70时,硬化性可能会减低,在大于3000时,可能会无充分的涂膜物性。
作为本发明中使用的(C)成分的胍化合物例如可举出如下述通式所示的化合物等。
上述通式中的m表示1至5的整数,R1′表示胺基、或非取代或由氟取代的碳原子数1至15的1价烃基,R2表示氢原子、或碳原子数1至4的烷基。
本发明中,这些胍化合物中优选使用稳定性及反应性的平衡较佳的乙酰胍胺、苯胍胺、及双氰二胺。
本发明中使用的(D)成分的酚化合物例如可举出如下述通式所示的化合物。
上述通式中的l表示0至4的整数,R1表示非取代或由氟取代的1价烃基。
本发明中,特别在反应性及稳定性的平衡的观点上,优选使用4,4′-联苯酚及/或3,3′,5,5′-四甲基-4,4′-联苯酚。
本发明的氰酸酯—环氧树脂组合物中,(A)成分与(B)成分的使用量,相对于(A)成分100质量份,(B)成分为1至10000质量份,优选10至1000质量份,更优选20至500质量份。
另外,本发明的氰酸酯—环氧树脂组合物中,(C)成分的使用量,相对于(A)成分与(B)成分的总量100质量份为3至60质量份,优选5至50质量份。
并且,本发明的氰酸酯—环氧树脂组合物中,(D)成分的使用量,相对于(A)成分与(B)成分的总量100质量份为0.1至50质量份,优选1至30质量份。
本发明中以(A)成分至(D)成分所制成的氰酸酯—环氧树脂组合物中,在不损及本发明效果的范围(10质量%以下)内,也可再适当地含有下述添加物。
黏度调整剂或整平剂等的表面活性剂、用以去除焊料的氧化皮膜等用途的助熔剂;着色用的染料或颜料;巴西棕榈蜡等的内加脱模剂;酚类、硫类等的抗氧化剂、受阻胺(hindered amine)类自由基捕获剂、紫外线吸收剂等抗劣化剂。
另外,本发明的氰酸酯—环氧树脂组合物中,依其需要也可共同使用玻璃纤维、碳纤维、纤维素、硅砂、水泥、高岭土、黏土、氢氧化铝、膨土、滑石、二氧化硅、二氧化硅细粉、二氧化钛、碳黑、石墨、氧化铁、沥青胶、金属粒子、金属包覆的树脂粒、聚硅氧橡胶等树脂粒子、可塑剂等填充剂、或颜料;增黏剂;触变剂(thixotropic agent);耦合剂;阻燃剂;消泡剂;防锈剂;胶质氧化硅、胶质氧化铝等常用的添加物,或其它二甲苯树脂、或石油树脂等黏着性树脂类等。这些添加物等对本发明的氰酸酯—环氧树脂组合物的使用比率,可依其用途适当地决定。
通过将本发明的氰酸酯—环氧树脂组合物以无溶剂一液型使用,例如可抑制VOC的发生,因而可提供对环境的负荷少的高安全性材料,且可应用于微隙部位的渗透及硬化等无法使用溶剂的用途上,具有上述优点。
本发明的无溶剂一液型氰酸酯—环氧树脂组合物,可使用于例如针对混凝土、水泥砂浆、各种金属、皮革、玻璃、橡胶、塑料、木材、布、纸等的涂料、或粘结剂等广泛的用途上。特别因为具有高耐热性及优良的粘结性,因此适合使用于半导体保护封装、或电子零部件粘结等的电子材料的用途、及汽车材料用途上。
以下再以制造例及实施例进一步详细说明本发明的无溶剂一液型氰酸酯—环氧树脂组合物,但本发明并不限定于此。
实施例1
氰酸酯(CE):Lonza公司制造的西亚纳多LeCy(商品名)
环氧树脂(EP):ADEKA(株)公司制造的EP-4901E(双酚F型环氧树脂,环氧当量168)(商品名)
苯胍胺(BG):日本碳化工业(株)公司制造的BG(商品名)
双氰二胺(DICY):ADEKA(株)公司制造的EH-3636AS(商品名)
4,4′-联苯酚(44BP):东京化成工业(株)公司制造的4,4′-联苯酚
双(4-羟苯基)砜(BPS):东京化成工业(株)公司制造的双(4-羟苯基)砜
将上述化合物以如下述表1掺混,实施如下的试验来评定其储存稳定性、硬化性、及玻璃转移温度,其结果如表1所示。
(黏度)
使用Brookfield E型旋转黏度计,以5rpm测定25℃下的黏度。
(胶化时间)
先在保持在各测定温度的热盘上滴下制成的组合物0.5g,再一边以刮勺混合,同时测定其至流动性消失为止的时间。
(玻璃转移温度)
使用SII纳米科技公司制造的差式扫描热量计(商品名:DSC6220),以升温速度10℃/分钟、扫描温度范围25至300℃条件测定,制作其DSC变化图。之后,以相同条件升温操作2次,测定热容量曲线上曲线变化点即为玻璃转移温度。
(粘结性)
依据日本JIS K 6850的方法,测定120℃×1小时硬化后钢板/钢板剪切粘结力。
表1
由上述表1可知,对氰酸酯及环氧树脂的复合树脂单独使用双氰二胺、苯胍胺、及联苯化合物(比较例1-1、1-2、1-3)时,可确定特别在低温下的硬化性不佳。同时可确定,对氰酸酯及环氧树脂的复合树脂使用胍化合物与本发明的特定的酚化合物以外的酚化合物的组合(比较例1-4、1-5)时,初始黏度显著提高,使稳定性显著降低。
与此相对,在本发明的实施例1-1、1-2中,可确实证明不但其稳定性优良,特别在低温下的硬化性,与各单独使用的情况(比较例1-1、1-2、1-3)比较极为优良。
工业实用性
本发明的无溶剂一液型氰酸酯—环氧树脂组合物,可提供具有优良的保存性及硬化性,且对环境的负荷减低而安全性高的材料,除此之外,因对微隙部位的渗透及硬化等,而无法使用溶剂的用途上也可应用,因此在产业上极为有用。
Claims (10)
2.根据权利要求1所述的无溶剂一液型氰酸酯—环氧复合树脂组合物,其特征在于,前述(C)成分的胍化合物为由下述通式所示的化合物的群中选择的至少一种;
其中,上述通式中的m表示1至5的整数,R1′表示胺基、或非取代或由氟取代的碳原子数1至15的1价烃基,R2表示氢原子、或碳原子数1至4的烷基。
3.根据权利要求2所述的无溶剂一液型氰酸酯—环氧复合树脂组合物,其特征在于,前述(C)成分的胍化合物为由乙酰胍胺、苯胍胺、双氰二胺之中选择的至少一种。
4.根据权利要求1或2所述的无溶剂一液型氰酸酯—环氧复合树脂组合物,其特征在于,前述(D)成分的酚化合物为4,4′-联苯酚及/或3,3′,5,5′-四甲基-4,4′-联苯酚。
6.一种硬化物,其特征在于,以权利要求1所述的氰酸酯—环氧复合树脂组合物聚合硬化所制成。
7.一种硬化物,其特征在于,以权利要求1所述的氰酸酯—环氧复合树脂组合物、与填充剂、颜料、增黏剂、触变剂、抗燃剂、消泡剂、防锈剂、胶质氧化硅、胶质氧化铝、及黏着性树脂类的群中选择的至少一种所构成的均一混合物硬化所制成。
8.一种封装用材料,其特征在于,以权利要求1所述的氰酸酯—环氧复合树脂组合物所制成。
9.一种粘结剂,其特征在于,以权利要求1所述的氰酸酯—环氧复合树脂组合物所制成。
10.一种硬化物的制造方法,其特征在于,以权利要求1所述的氰酸酯—环氧复合树脂组合物在模型内硬化。
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