TWI731983B - 含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物及其製造方法、使用上述化合物之組成物及硬化物 - Google Patents
含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物及其製造方法、使用上述化合物之組成物及硬化物 Download PDFInfo
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- TWI731983B TWI731983B TW106118379A TW106118379A TWI731983B TW I731983 B TWI731983 B TW I731983B TW 106118379 A TW106118379 A TW 106118379A TW 106118379 A TW106118379 A TW 106118379A TW I731983 B TWI731983 B TW I731983B
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- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
Description
本發明係關於一種含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物及其製造方法、使用上述化合物之組成物及硬化物。
作為電子機器用電路基板材料,廣泛使用有使環氧樹脂、苯并樹脂、BT(雙順丁烯二醯亞胺-三)樹脂等熱硬化性樹脂含浸至玻璃布中並進行加熱乾燥而獲得之預浸體、將該預浸體加熱硬化而成之積層板、將該積層板與該預浸體進行組合並進行加熱硬化而成之多層板。
近年來,於該等各種用途、尤其是於尖端材料用途中,要求以耐熱性、介電性、耐濕可靠性為代表之各性能之進一步提昇、及兼具該等特性並且亦表現出高度難燃性之材料、組成物。
其中,雙順丁烯二醯亞胺(BMI)由於表現出較以往之環氧樹脂、酚系樹脂優異之耐熱性(高Tg及高耐熱分解性),故而近年來除面向上述電材用途之研究以外,亦作為面向以SiC功率半導體為代表之下一代裝置之樹脂材料受到關注。
於市場上,具有DDM(4,4'-二胺基二苯甲烷)或DDE(4,4'-二胺基二苯醚)骨架之BMI作為高耐熱樹脂進行流通。然而,此種高耐熱性之BMI係高熔點,因此存在只能於有限之用途中使用之問題。
[專利文獻1]日本特開2015-193628號公報
因此,本發明之目的在於提供一種低熔點且耐熱性優異之化合物。
本發明人等進行努力研究,結果發現,藉由具有具備2個苯環之結構,且具有經取代或未經取代烯丙基與順丁烯二醯亞胺基各1個以上之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物而解決上述問題。
即,本發明係關於一種含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物,其由下述通式(1)表示。
此時,上述苯環可具有取代基,X表示直接鍵或2價之連結基。
根據本發明,提供一種低熔點且耐熱性優異之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物。藉此,可較佳地用於例如耐熱 構件或電子構件、尤其是半導體密封材、電路基板、增層(build-up)膜、增層基板、接著劑、抗蝕劑材料、纖維強化樹脂之基質樹脂、高耐熱性之預浸體、耐熱塗料用樹脂等用途。
<含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物>
本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物係由下述通式(1)表示。
此處,本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物之特徵在於:具有下述之式(4-1)或(4-2)所表示之具有2個苯環之結構中之任一者。苯環可具有取代基,亦可不具有取代基,鍵結方式並無特別限定。苯環彼此可直接鍵結,亦可經由連結基進行鍵結,苯環彼此亦可縮合而形成縮合環。再者,本說明書中,所謂「經取代或未經取代烯丙基」,意指鍵結於構成烯丙基、烯丙基之雙鍵之碳原子之氫原子之至少1個被取代為甲基之基。經取代或未經取代烯丙基具體而言,包含以下之結構式所表示之基。
再者,上述式中,「*」表示與其他基鍵結之部位。其中,經取代或未經取代烯丙基較佳為包含結構式所表示之基。
式(1)中,n及m分別獨立,為1~5之整數,較佳為2~5,更佳為2~3,進一步較佳為2。再者,若n為2以上,則有熔點降低之傾向,故而較佳。又,若m為2以上,則有耐熱性提昇之傾向,故而較佳。
作為m與n之比率,為m:n=1:5~5:1,較佳為1:2~2:1,更佳為1:1。再者,若m與n之比率處於上述範圍內,則能夠兼顧耐熱性與低熔點,故而較佳。
Aly係下述式(2)所表示之含有經取代或未經取代烯丙基之基。
式(2)中,Z為直接鍵或可具有取代基之碳數1~10之烴 基,R1、R2、及R3分別獨立,表示氫原子或甲基。
上述碳數1~10之烴基例如可列舉:伸烷基(alkylene group)、伸烯基、伸炔基、伸環烷基、伸芳基、及將其等組合複數個而成之基。此時,碳數1~10之烴基為2價之基。
作為上述伸烷基,可列舉:亞甲基、次甲基、伸乙基、伸丙基、伸丁基、伸戊基、伸己基等。
作為上述伸烯基,可列舉:伸乙烯基、1-甲基伸乙烯基、伸丙烯基、伸丁烯基、伸戊烯基等。
作為上述伸炔基,可列舉:伸乙炔基、伸丙炔基、伸丁炔基、伸戊炔基、伸己炔基等。
作為伸環烷基,可列舉:伸環丙基、伸環丁基、伸環戊基、伸環己基等。
作為伸芳基,可列舉:伸苯基、甲伸苯基、苯二甲基、伸萘基等。
其等中,Z較佳為直接鍵或亞甲基,更佳為直接鍵。
作為Aly之具體結構,可列舉以下之結構式者。
其中,Aly較佳為以下之結構式所表示者。
又,MI係下述式(3)所表示之順丁烯二醯亞胺基。
此時,式(3)中,R4及R5分別獨立,表示氫原子或甲基。
於一實施形態中,含有經取代或未經取代烯丙基之基與順丁烯二醯亞胺基之鍵結位置並無特別限定,若順丁烯二醯亞胺基與含有經取代或未經取代烯丙基之基存在於同一個苯環上,則耐熱性進一步提昇,故而較佳。
進一步,A係下述式(4-1)或(4-2)所表示之具有2個苯環之結構。
此時,苯環亦可具有取代基。又,X表示直接鍵或2價之連結基。
作為上述2價之連結基,例如可列舉:可具有取代基之碳數1~3之烴基、氧原子、羰基、硫原子、磺醯基、可具有取代基之2價之脂環結構等。
作為碳數1~3之烴基,可列舉:亞甲基、伸乙基、伸丙基等。
又,作為上述2價之脂環結構,可列舉:伸環丙基、伸環丁基、伸環戊基、伸環己基等。
於上述烴基、上述2價之脂環結構具有取代基之情形時,作為該取代基,可列舉:甲基、乙基、丙基、丁基等碳數1~5之烷基;氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、溴甲基、二溴甲基、三溴甲基、氯氟甲基、五氟乙基等碳數1~5之鹵化烷基等。
其等之中,X較佳為可具有取代基之碳數1~3之烴基、氧原子、硫原子,更佳為可具有取代基之亞甲基、氧原子,進一步較佳為亞甲基、伸乙基、亞乙基、亞異丙基、1-三氟亞甲基、1,1-二(三氟甲基)亞甲基。
作為較佳之A之結構,可列舉以下之式(5-1)~(5-8)所表示之結構之任一者。
再者,於式(5-1)~(5-8)中,於無損本發明之效果之範圍內,結構中之苯環亦可具有取代基,即,苯環結構之氫原子亦可經取代基取代。作為上述取代基,可列舉公知慣用者。例如可列舉:可具有取代基之碳數1~6之烴基、鹵素原子、羥基、胺基、醯胺基、脲基、胺酯(urethane)基、羧基、烷氧基、硫醚基、醯基、醯氧基、烷氧羰基、氰基、硝基等。
例如,上述式(5-1)及(5-2)由於為剛性結構,又,(5-3)及(5-4)由於苯環彼此之鍵結部分具有分極,故而可獲得耐熱分解性優異之化合物。
又,上述(5-5)~(5-8)之結構可獲得接著性優異之化合物。
其等之中,A就低熔點、機械特性(彎曲模數、彎曲應變、彎曲強度)、流動性之觀點而言,較佳為(5-5)~(5-7)之任一者。
上述含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合 物藉由具有2個苯環,而本發明之化合物之耐熱性、尤其是耐熱分解溫度提高。又,藉由具有順丁烯二醯亞胺基,而玻璃轉移溫度上升,因此耐熱性進一步提昇。又,藉由經取代或未經取代烯丙基,而反應性提昇,並且熔點降低,因此處理性提昇而可於各種用途中較佳地使用。
又,於一實施形態中,含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物其溶劑溶解性亦優異。
以往之順丁烯二醯亞胺化合物雖具有特定之耐熱性,但溶劑溶解性較低,而無法以塗佈液等與溶劑併用之形態使用,而成為順丁烯二醯亞胺化合物之用途被限定之要因之一。
相對於此,含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物由於溶劑溶解性優異,故而亦可以塗佈液等形態使用。藉此,亦可較佳地應用於以往之順丁烯二醯亞胺化合物所無法應用之耐熱塗料用樹脂等用途。
再者,含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物其溶劑溶解性優異之原因並不明確,推測原因在於:結構中之經取代或未經取代烯丙基會緩和源自芳香環之結晶性。
作為本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物,尤佳之結構係以下之式(6-1)~(6-16)所例示之結構。
其等之中,較佳為(6-1)~(6-12)所表示之結構,更佳為(6-1)、(6-2)、(6-5)、(6-6)、(6-9)、(6-10)、(6-11)、(6-12)所表示之結構,進一步較佳為(6-1)、(6-2)、(6-5)、(6-6)所表示之結構。
<含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物之製造方法>
本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物之製造方法並無特別限定,可藉由經以下之步驟而有效率地進行製造。
於一實施形態中,含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物可藉由下述步驟(1-1)~(1-4)進行製造;
1-1)將具有2個苯環之含羥基之芳香族胺基化合物之胺基進行保護的步驟
1-2)向1-1)中所獲得之化合物之羥基導入經取代或未經取代烯丙基的步驟
1-3)自1-2)中所獲得之化合物之保護胺基進行去保護的步驟
1-4)將1-3)中所獲得之化合物之胺基進行順丁烯二醯亞胺化的步驟
藉由包含上述步驟之製造方法,可有效率且無副產物地製造本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物。
此處,藉由於步驟(1-1)中使用具有2個苯環之含羥基之芳香族胺基化合物,可製造本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物,該含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物之特徵在於:其係具有具備2個苯環之結構,且具有1個以上之具有經取代或未經取代烯丙基之基,進一步具有1個以上之順丁烯二醯亞胺基之化合物。
作為上述具有2個苯環之含羥基之芳香族胺基化合物,較佳為可列舉:具有式(4-1)或(4-2)所表示之結構、與羥基及胺基之化合物。具體而言,可列舉:2,2-雙(3-胺基-4-羥基苯基)丙烷、2,2-雙(3-胺基-4-羥基苯基)六氟丙烷、2,2-雙(3-胺基-4-羥基苯基)碸、4,4'-二胺基-3,3'-二羥基聯苯、3,3'-二胺基-4,4'-二羥基聯苯、5,5'-亞甲基雙(2-胺基苯酚)等以往公知之化合物,但並不限定於其等。
再者,作為製造上述具有2個苯環之含羥基之芳香族胺基化合物之方法,可列舉:於將含羥基之芳香族化合物硝基化後進行還原之方法。
步驟1-1)中之胺基之保護只要使用公知慣用之方法即可,例如可藉由進行乙醯化而進行保護。此時,對於乙醯化,只要使用公知慣用之乙醯化劑即可,例如可列舉乙酸酐、乙醯氯等。
於步驟1-2)中,例如使含有經取代或未經取代烯丙基之化合物之鹵化物於鹼的存在下與胺基得到保護之含羥基之芳香族胺基化合物之羥基進行反應,藉此能夠導入經取代或未經取代烯丙基。作為含經取代或未經取代烯丙基之化合物之鹵化物,可列舉:烯丙基溴、甲基烯丙基溴(3-溴-2-甲基-1-丙烯)、烯丙基氯、甲基烯丙基氯(3-氯-2-甲基-1-丙烯)、順式-1-氯-2-丁烯、反式-1-氯-2-丁烯、1-氯-3-甲基-2-丁烯、1-溴-3-甲基-2-丁烯等。又,作為鹼,可列舉碳酸鉀等。
於步驟1-3)與步驟1-4)中,將受到保護之胺基去保護,將該胺基進行順丁烯二醯亞胺化。胺基之順丁烯二醯亞胺化例如可藉由使以下式(7)所表示之化合物進行反應而進行順丁烯二醯亞胺化。
式(7)中,R4及R5分別獨立地表示氫原子或甲基。
作為式(7)所表示之化合物,例如可列舉:順丁烯二酸酐、檸康酸酐、2,3-二甲基順丁烯二酸酐等。
藉由經上述步驟,可製造本發明之含有經取代或未經取代烯 丙基之順丁烯二醯亞胺化合物,該含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物之特徵在於:其係具有具備2個苯環之結構,且具有1個以上之具有經取代或未經取代烯丙基之基,進一步具有1個以上之順丁烯二醯亞胺基之化合物。
於合成本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物之情形時,亦有於反應物中殘留未反應單體、或者生成作為生成物之與含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物不同之其他化合物之情況。作為其他化合物,例如可列舉:未閉環之醯胺酸(amic acid)、異醯亞胺、單體類或生成物之低聚物等。關於其等含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物以外之物質,可藉由經精製步驟而去除,亦可視用途,於含有之狀態下使用。
<組成物>
本發明之組成物含有本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物。
本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物由於低熔點且耐熱性優異,故而使含有其之組成物硬化而獲得之硬化物之耐熱分解性優異,而為高玻璃轉移溫度、低線膨脹,因此可較佳地用於耐熱構件或電子構件。
又,如上所述,於一實施形態中,含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物之溶劑溶解性亦優異。因此,於較佳之一實施形態中,係提供含有含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物與分散介質之組成物。該組成物可較佳地應用於耐熱塗料用途等。
<反應性化合物>
本發明之組成物亦可含有含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物以外之反應性化合物。藉由含有該反應性化合物,而能夠對樹脂賦予反應性或耐熱性、處理性等各種特徵。
此處所謂反應性化合物,係具有反應性基之化合物,可為單體,亦可為低聚物,亦可為聚合物。
作為反應性基,可為不會與本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物進行反應之官能基,亦可為會與本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物進行反應之官能基,但為了更為提高耐熱性,較佳為會與本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物進行反應之官能基。
作為具有環氧基之化合物,例如可列舉:環氧樹脂、苯氧基樹脂。
作為具有氰氧基之化合物,可列舉氰酸酯樹脂。
作為具有順丁烯二醯亞胺基之化合物,可列舉:順丁烯二醯亞胺樹脂、雙順丁烯二醯亞胺樹脂。
作為具有苯酚性羥基之化合物,可列舉:苯酚酚醛清漆樹脂、甲酚酚醛清漆樹脂、二環戊二烯改質酚系樹脂、苯酚芳烷基樹脂、萘酚芳烷基樹脂、聯苯芳烷基樹脂。
作為具有胺基之化合物,可列舉:DDM(4,4'-二胺基二苯甲烷)或DDE(4,4'-二胺基二苯醚)、3,4'-二胺基二苯醚、2,2-{雙4-(4-胺基苯氧基)苯基}丙烷、4,4'-雙(4-胺基苯氧基)聯苯等芳香族胺基化合物。
作為具有含有碳-碳間雙鍵之基之化合物,可列舉:順丁烯二醯亞胺化合物、乙烯系化合物、(甲基)烯丙基系化合物等。再者,於本說明書中,於將有特別事先說明之情形除外而僅記載為「順丁烯二醯亞胺化合物」時,意指本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物以外的順丁烯二醯亞胺化合物。同樣地於將有特別事先說明之情形除外而僅記載為「(甲基)烯丙基系化合物」時,意指本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物以外的(甲基)烯丙基系化合物。
上述之反應性化合物可具有僅1種之反應性基,亦可具有複數種,官能基數可為1個,亦可為複數個。又,亦可同時使用複數種。
作為較佳之反應性化合物,可列舉:環氧樹脂、苯氧基樹脂、氰酸酯樹脂、順丁烯二醯亞胺化合物、乙烯系化合物、芳香族胺基化合物等。
其中,尤佳為順丁烯二醯亞胺化合物、氰酸酯樹脂、環氧樹脂、芳香族胺基化合物。
順丁烯二醯亞胺化合物與本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物係藉由順丁烯二醯亞胺基彼此之自我加成反應或烯丙基與順丁烯二醯亞胺基之烯反應,而交聯密度提高,其結果為,耐熱性、尤其是玻璃轉移溫度提高。
通常為了使用順丁烯二醯亞胺化合物而獲得均一之硬化物,而必需高溫且長時間之硬化條件,因此於大多數情形時,為了促進反應而併用過氧化物系觸媒。然而,本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物即便於不使用觸媒之情形時,硬化反應亦會進行,而能夠獲得均一之硬化物。存在因使用過氧化物系觸媒而組成物之黏度上升、或適用期降低;又,因於硬化物中殘存微量之過氧化物而導致物性低下等問題,但本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物亦可不使用過氧化物系硬化劑,因此能夠解決其等問題。
氰酸酯樹脂與本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物之硬化物表現出優異之介電性。
環氧樹脂可藉由與本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物併用而對硬化物賦予韌性或金屬密接性。
芳香族胺基化合物藉由胺基與順丁烯二醯亞胺基之麥可加成反應而交聯密度提高,從而耐熱分解溫度、玻璃轉移溫度提高。
作為環氧樹脂,只要具有環氧基,則無特別限定,例如可列舉:雙酚A型環氧樹脂、雙酚F型環氧樹脂、雙酚E型環氧樹脂、雙酚S型環氧樹脂、雙酚硫醚型環氧樹脂、苯醚型環氧樹脂、萘醚型環氧樹脂、聯苯型環氧樹脂、四甲基聯苯型環氧樹脂、聚羥基萘型環氧樹脂、苯酚酚 醛清漆型環氧樹脂、甲酚酚醛清漆型環氧樹脂、三苯甲烷型環氧樹脂、四苯乙烷型環氧樹脂、二環戊二烯-苯酚加成反應型環氧樹脂、苯酚芳烷基型環氧樹脂、萘酚酚醛清漆型環氧樹脂、萘酚芳烷基型環氧樹脂、萘酚-苯酚共縮酚醛清漆型環氧樹脂、萘酚-甲酚共縮酚醛清漆型環氧樹脂、萘醚型環氧樹脂、芳香族烴甲醛樹脂改質酚系樹脂型環氧樹脂、聯苯改質酚醛清漆型環氧樹脂、蒽型環氧樹脂等。其等可分別單獨地使用,亦可併用2種以上。
苯氧基樹脂較佳為基於二酚、與表氯醇等表鹵醇之高分子量熱塑性聚醚樹脂,且重量平均分子量為20,000~100,000。作為苯氧基樹脂之結構,例如可列舉:具有選自雙酚A骨架、雙酚F骨架、雙酚S骨架、雙酚苯乙酮骨架、酚醛清漆骨架、聯苯骨架、茀骨架、二環戊二烯骨架、降莰烯骨架、萘骨架、蒽骨架、金剛烷骨架、萜烯骨架、三甲基環己烷骨架中之1種以上之骨架者。
作為氰酸酯樹脂,例如可列舉:雙酚A型氰酸酯樹脂、雙酚F型氰酸酯樹脂、雙酚E型氰酸酯樹脂、雙酚S型氰酸酯樹脂、雙酚硫醚型氰酸酯樹脂、苯醚型氰酸酯樹脂、萘醚型氰酸酯樹脂、聯苯型氰酸酯樹脂、四甲基聯苯型氰酸酯樹脂、聚羥基萘型氰酸酯樹脂、苯酚酚醛清漆型氰酸酯樹脂、甲酚酚醛清漆型氰酸酯樹脂、三苯甲烷型氰酸酯樹脂、四苯乙烷型氰酸酯樹脂、二環戊二烯-苯酚加成反應型氰酸酯樹脂、苯酚芳烷基型氰酸酯樹脂、萘酚酚醛清漆型氰酸酯樹脂、萘酚芳烷基型氰酸酯樹脂、萘酚-苯酚共縮酚醛清漆型氰酸酯樹脂、萘酚-甲酚共縮酚醛清漆型氰酸酯樹脂、芳香族烴甲醛樹脂改質酚系樹脂型氰酸酯樹脂、聯苯改質酚 醛清漆型氰酸酯樹脂、蒽型氰酸酯樹脂等。其等可分別單獨地使用,亦可併用2種以上。
其等氰酸酯樹脂之中,尤其是就獲得耐熱性優異之硬化物之方面而言,較佳為使用雙酚A型氰酸酯樹脂、雙酚F型氰酸酯樹脂、雙酚E型氰酸酯樹脂、聚羥基萘型氰酸酯樹脂、萘醚型氰酸酯樹脂、酚醛清漆型氰酸酯樹脂,就獲得介電性優異之硬化物之方面而言,較佳為二環戊二烯-苯酚加成反應型氰酸酯樹脂。
作為順丁烯二醯亞胺化合物,例如可列舉:下述結構式(i)~(iii)之任一者所表示之各種化合物等。
式(i)中,R係s價之有機基,α及β分別為氫原子、鹵素原子、烷基、芳基之任一者,s為1以上之整數。
式(ii)中,R係氫原子、烷基、芳基、芳烷基、鹵素原子、羥基、烷氧基之任一者,s為1~3之整數,t以重複單位之平均計為0~10。
式(iii)中,R係氫原子、烷基、芳基、芳烷基、鹵素原子、羥基、烷氧基之任一者,s為1~3之整數,t以重複單位之平均計為0~10。
其等順丁烯二醯亞胺化合物可分別單獨地使用,亦可併用2種以上。
作為化合物,並無特別限制,例如可列舉:雙酚F與福馬林與苯胺之反應生成物(F-a型苯并樹脂)或4,4'-二胺基二苯甲烷與福馬林與苯酚之反應生成物(P-d型苯并樹脂)、雙酚A與福馬林與苯胺之反應生成物、二羥基二苯醚與福馬林與苯胺之反應生成物、二胺基二苯醚與福馬林與苯酚之反應生成物、二環戊二烯-苯酚加成型樹脂與福馬林與苯胺之反應生成物、酚酞與福馬林與苯胺之反應生成物、二羥基二苯硫醚與福馬林與苯胺之反應生成物等。其等可分別單獨地使用,亦可併用2種以上。
作為乙烯系化合物,例如可列舉:(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸三級丁酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸月桂酯等具有碳原子數為1~22之烷基之(甲基)丙烯酸烷基酯類;(甲基)丙烯酸苄酯、(甲基)丙烯酸2-苯基乙酯等(甲基)丙烯酸 芳烷酯類;(甲基)丙烯酸環己酯、(甲基)丙烯酸異莰酯等(甲基)丙烯酸環烷基酯類;(甲基)丙烯酸2-甲氧基乙酯、(甲基)丙烯酸4-甲氧基丁酯等(甲基)丙烯酸ω-烷氧基烷基酯類;乙酸乙烯酯、丙酸乙烯酯、新戊酸乙烯酯、苯甲酸乙烯酯等羧酸乙烯酯類;丁烯酸甲酯、丁烯酸乙酯等丁烯酸之烷基酯類;順丁烯二酸二甲酯、順丁烯二酸二-正丁酯、反丁烯二酸二甲酯、伊康酸二甲酯等不飽和二元酸之二烷基酯類;乙烯、丙烯等α-烯烴類;偏二氟乙烯、四氟乙烯、六氟丙烯、三氟氯乙烯等氟烯烴類;乙基乙烯醚、正丁基乙烯醚等烷基乙烯醚類;環戊基乙烯醚、環己基乙烯醚等環烷基乙烯醚類;N,N-二甲基(甲基)丙烯醯胺、N-(甲基)丙烯醯啉、N-(甲基)丙烯醯吡咯啶、N-乙烯基吡咯啶酮等含有三級醯胺基之單體類等。
作為(甲基)烯丙基系化合物,可列舉:乙酸烯丙酯、烯丙基氯、己酸烯丙酯、辛酸烯丙酯、月桂酸烯丙酯、棕櫚酸烯丙酯、硬脂酸烯丙酯、苯甲酸烯丙酯、乙醯乙酸烯丙酯、乳酸烯丙酯等烯丙酯類;烯丙氧基甲醇、烯丙氧基乙醇等烯丙氧基醇;鄰苯二甲酸二烯丙酯、間苯二甲酸二烯丙酯、三聚氰酸二烯丙酯、三聚異氰酸二烯丙酯、新戊四醇二烯丙醚、三羥甲基丙烷二烯丙醚、甘油二烯丙醚、雙酚A二烯丙醚、雙酚F二烯丙醚、乙二醇二烯丙醚、二乙二醇二烯丙醚、三乙二醇二烯丙醚、丙二醇二烯丙醚、二丙二醇二烯丙醚、三丙二醇二烯丙醚等含有2個烯丙基之化合物;三聚異氰酸三烯丙酯、新戊四醇三烯丙醚、新戊四醇四烯丙醚、三羥甲基丙烷三烯丙醚等含有3個以上之烯丙基之化合物;等、或者其等化合物之甲基烯丙基體。
於本發明之組成物中,存在順丁烯二醯亞胺基與經取代或未經取代烯丙基兩者。順丁烯二醯亞胺基與經取代或未經取代烯丙基之比率並無特別限定,較佳為順丁烯二醯亞胺基莫耳數:經取代或未經取代烯丙基莫耳數=1:10~10:1,若為1:5~5:1,則耐熱性優異,故而較佳。尤其是於1:2~2:1之情形時,耐熱性與摻合物黏度之平衡性優異,故而較佳。再者,於組成物中一併含有本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物、與具有順丁烯二醯亞胺基之順丁烯二醯亞胺化合物、或具有(甲基)烯丙基之(甲基)烯丙基系化合物等的情形時,「順丁烯二醯亞胺基莫耳數」及「經取代或未經取代烯丙基莫耳數」係將含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物以外者亦包括在內而算出。
<填料>
本發明之組成物除含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物以外,亦可進一步含有填料。作為填料,可列舉無機填料與有機填料。作為無機填料,例如可列舉無機微粒子。
關於無機微粒子,例如作為耐熱性優異者,係氧化鋁、氧化鎂、氧化鈦、氧化鋯、二氧化矽(石英、煙熏二氧化矽、沈澱二氧化矽、矽酸酐、熔融二氧化矽、晶質二氧化矽、超微粉無定型二氧化矽等)等;作為導熱性優異者,係氮化硼、氮化鋁、氧化鋁、氧化鈦、氧化鎂、氧化鋅、氧化矽、金剛石等;作為導電性優異者,係使用金屬單質成分或合金(例如,鐵、銅、鎂、鋁、金、銀、鉑、鋅、錳、不鏽鋼等)之金屬填料及/或金屬被覆填料;作為阻隔性優異者,係雲母、黏土、高嶺土、滑石、 沸石、矽灰石、膨潤石等礦物等或鈦酸鉀、硫酸鎂、海泡石、硬矽鈣石、硼酸鋁、碳酸鈣、氧化鈦、硫酸鋇、氧化鋅、氫氧化鎂;作為折射率較高者,係鈦酸鋇、氧化鋯、氧化鈦等;作為表現出光觸媒性者,係鈦、鈰、鋅、銅、鋁、錫、銦、磷、碳、硫、銩、鎳、鐵、鈷、銀、鉬、鍶、鉻、鋇、鉛等光觸媒金屬、上述金屬之複合物、其等之氧化物等;作為耐磨耗性優異者,係二氧化矽、氧化鋁、氧化鋯、氧化鎂等金屬、及其等之複合物及氧化物等;作為導電性優異者,係銀、銅等金屬、氧化錫、氧化銦等;作為絕緣性優異者,係二氧化矽等;作為紫外線遮蔽優異者,係氧化鈦、氧化鋅等。
其等無機微粒子只要視用途而適時選擇即可,可單獨地使用,亦可組合複數種而使用。又,上述無機微粒子除例中所列舉之特性以外,亦具有各種特性,因此只要視用途而適時選擇即可。
例如於使用二氧化矽作為無機微粒子之情形時,可無特別限定地使用粉末狀之二氧化矽或膠體二氧化矽等公知之二氧化矽微粒子。作為市售之粉末狀之二氧化矽微粒子,例如可列舉:日本AEROSIL(股)製造之AEROSIL 50、200;旭硝子(股)製造之SILDEX H31、H32、H51、H52、H121、H122;Nippon Silica Industry(股)製造之E220A、E220;FUJI SILYSIA CHEMICAL(股)製造之SYLYSIA470;日本板硝子(股)製造之SG FLAKE等。
又,作為市售之膠體二氧化矽,例如可列舉:日產化學工業(股)製造之甲醇二氧化矽溶膠、IPA-ST、MEK-ST、NBA-ST、XBA-ST、DMAC-ST、ST-UP、ST-OUP、ST-20、ST-40、ST-C、ST -N、ST-O、ST-50、ST-OL等。
亦可使用經表面修飾之二氧化矽微粒子,例如可列舉:上述二氧化矽微粒子經具有疏水性基之反應性矽烷偶合劑表面處理者、或經具有(甲基)丙烯醯基之化合物修飾者。作為經具有(甲基)丙烯醯基之化合物修飾之市售之粉末狀二氧化矽,可列舉日本AEROSIL(股)製造之AEROSIL RM50、R711等;作為經具有(甲基)丙烯醯基之化合物修飾之市售之膠體二氧化矽,可列舉日產化學工業(股)製造之MIBK-SD等。
上述二氧化矽微粒子之形狀並無特別限定,可使用球狀、中空狀、多孔質狀、棒狀、板狀、纖維狀、或不定形狀者。又,一次粒徑較佳為5~200nm之範圍。若為5nm以上,則將無機微粒子較佳地分散於分散體中,若為200nm以下,則可防止硬化物之強度降低。
作為氧化鈦微粒子,不僅可使用體質顏料,亦可使用紫外線光響應型光觸媒,例如可使用銳鈦礦型氧化鈦、金紅石型氧化鈦、板鈦礦型氧化鈦等。進一步,亦可使用以於氧化鈦之結晶結構中摻雜異種元素而與可見光響應之方式進行設計所得之粒子。作為摻雜於氧化鈦之元素,可較佳地使用氮、硫、碳、氟、磷等陰離子元素;或鉻、鐵、鈷、錳等陽離子元素。又,作為形態,可使用粉末、分散於有機溶劑中或水中之溶膠或漿料。作為市售之粉末狀之氧化鈦微粒子,例如可列舉日本AEROSIL(股)製造之AEROSIL P-25、TAYCA(股)製造之ATM-100等。又,作為市售之漿料狀之氧化鈦微粒子,例如可列舉TAYCA(股)TKD-701等。
<纖維質基質>
本發明之組成物除含有經取代或未經取代烯丙基之順丁烯二醯亞胺化 合物以外,亦可進一步含有纖維質基質。本發明之纖維質基質並無特別限定,較佳為纖維強化樹脂所使用者,可列舉無機纖維或有機纖維。
作為無機纖維,除碳纖維、玻璃纖維、硼纖維、氧化鋁纖維、碳化矽纖維等無機纖維以外,亦可列舉碳纖維、活性碳纖維、石墨纖維、玻璃纖維、碳化鎢纖維、碳化矽纖維(silicon carbide fiber)、陶瓷纖維、氧化鋁纖維、天然纖維、玄武岩等之礦物纖維、硼纖維、氮化硼纖維、碳化硼纖維、及金屬纖維等。作為上述金屬纖維,例如可列舉:鋁纖維、銅纖維、黃銅纖維、不鏽鋼纖維、鋼絲纖維。
作為有機纖維,可列舉:由聚酯、芳香族聚醯胺、PBO(聚對伸苯基苯并唑)、聚苯硫醚、聚酯、丙烯酸樹脂、聚醯胺、聚烯烴、聚乙烯醇、聚芳酯等樹脂材料所構成之合成纖維;或纖維素、紙漿、綿、羊毛、絹等天然纖維;蛋白質、多肽、海藻酸等再生纖維等。
其中,碳纖維與玻璃纖維由於產業上利用範圍較廣,故而較佳。其等之中,可僅使用一種,亦可同時使用複數種。
本發明之纖維質基質可為纖維之集合體,纖維可連續,亦可為不連續狀,可為織布狀,亦可為不織布狀。又,可為將纖維於一方向上整齊排列之纖維束,亦可為並排纖維束而成之片狀。又,亦可為纖維之集合體具有厚度之立體形狀。
<分散介質>
本發明之組成物亦可以調整組成物之固形物成分量或黏度為目的而使用分散介質。作為分散介質,只要為無損本發明之效果之液狀介質即可,可列舉:各種有機溶劑、液狀有機聚合物等。
作為上述有機溶劑,例如可列舉:丙酮、甲基乙基酮(MEK)、甲基異丁基酮(MIBK)等酮類;四氫呋喃(THF)、二氧戊環等環狀醚類;乙酸甲酯、乙酸乙酯、乙酸丁酯等酯類;甲苯、二甲苯等芳香族類;卡必醇、賽路蘇、甲醇、異丙醇、丁醇、丙二醇單甲醚等醇類,可將其等單獨地使用或併用其等而使用,其中,就塗佈時之揮發性或溶劑回收之方面而言,較佳為甲基乙基酮。
上述所謂液狀有機聚合物,係不會直接有助於硬化反應之液狀有機聚合物,例如可列舉:含羧基之聚合物改質物(Flowlen G-900、NC-500:共榮社)、丙烯酸系聚合物(Flowlen WK-20:共榮社)、特殊改質磷酸酯之胺鹽(HIPLAAD ED-251:楠本化成)、改質丙烯酸系嵌段共聚物(DISPERBYK2000;BYK-Chemie)等。
<樹脂>
又,本發明之組成物亦可具有本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物以外之樹脂。作為樹脂,只要為無損本發明之效果之範圍,則只要摻合公知慣用之樹脂即可,例如可使用熱硬化性樹脂或熱塑性樹脂。
所謂熱硬化性樹脂,係指具有藉由加熱或者輻射或觸媒等手段進行硬化時實質上不熔且可變為不融性之特性的樹脂。作為其具體例,可列舉:酚系樹脂、尿素樹脂、三聚氰胺樹脂、苯胍(benzoguanamine)樹脂、醇酸樹脂、不飽和聚酯樹脂、乙烯酯樹脂、對酞酸二烯丙酯樹脂、環氧樹脂、聚矽氧樹脂、胺酯樹脂、呋喃樹脂、酮樹脂、二甲苯樹脂、熱硬化性聚醯亞胺樹脂、苯并樹脂、活性酯樹脂、苯胺樹脂、氰酸酯樹 脂、苯乙烯-順丁烯二酸酐(SMA)樹脂、藉由本發明而獲得之含烯丙基之順丁烯二醯亞胺化合物以外之順丁烯二醯亞胺樹脂等。其等熱硬化性樹脂可使用1種或併用2種以上而使用。
所謂熱塑性樹脂,係指能夠藉由加熱進行熔融成形之樹脂。作為其具體例,可列舉:聚乙烯樹脂、聚丙烯樹脂、聚苯乙烯樹脂、橡膠改質聚苯乙烯樹脂、丙烯腈-丁二烯-苯乙烯(ABS)樹脂、丙烯腈-苯乙烯(AS)樹脂、聚甲基丙烯酸甲酯樹脂、丙烯酸系樹脂、聚氯乙烯樹脂、聚偏二氯乙烯樹脂、聚對酞酸乙二酯樹脂、乙烯-乙烯醇樹脂、乙酸纖維素樹脂、離子聚合物樹脂、聚丙烯腈樹脂、聚醯胺樹脂、聚縮醛樹脂、聚對酞酸丁二酯樹脂、聚乳酸樹脂、聚苯醚樹脂、改質聚苯醚樹脂、聚碳酸酯樹脂、聚碸樹脂、聚苯硫醚樹脂、聚醚醯亞胺樹脂、聚醚碸樹脂、聚芳酯樹脂、熱塑性聚醯亞胺樹脂、聚醯胺醯亞胺樹脂、聚醚醚酮樹脂、聚酮樹脂、液晶聚酯樹脂氟樹脂、對排聚苯乙烯樹脂、環狀聚烯烴樹脂等。其等熱塑性樹脂可使用1種或併用2種以上而使用。
<硬化劑>
本發明之組成物亦可視摻合物而使用硬化劑。例如可列舉:胺系硬化劑、醯胺系硬化劑、酸酐系硬化劑、苯酚系硬化劑、活性酯系硬化劑、含羧基之硬化劑、硫醇系硬化劑等各種硬化劑。
作為胺系硬化劑,可列舉:二胺基二苯甲烷、二胺基二苯乙烷、二胺基二苯醚、二胺基二苯基碸、鄰苯二胺、間苯二胺、對苯二胺、間苯二甲胺、對苯二甲胺、二乙基甲苯二胺、二伸乙基三胺、三伸乙基四胺、異佛酮二胺、咪唑、BF3-胺錯合物、胍衍生物、胍胺衍生物等。
作為醯胺系硬化劑,可列舉:雙氰胺、由次亞麻油酸之二聚物與伸乙基二胺所合成之聚醯胺樹脂等。
作為酸酐系硬化劑,可列舉:鄰苯二甲酸酐、1,2,4-苯三甲酸酐、焦蜜石酸二酐、順丁烯二酸酐、四氫鄰苯二甲酸酐、甲基四氫鄰苯二甲酸酐、甲基耐地酸酐(methyl nadic anhydride)、六氫鄰苯二甲酸酐、甲基六氫鄰苯二甲酸酐等。
作為苯酚系硬化劑,可列舉:雙酚A、雙酚F、雙酚S、間苯二酚、鄰苯二酚、對苯二酚、茀雙酚、4,4'-聯苯二酚、4,4',4"-三羥基三苯甲烷、萘二醇、1,1,2,2-四(4-羥基苯基)乙烷、杯芳烴、苯酚酚醛清漆樹脂、甲酚酚醛清漆樹脂、芳香族烴甲醛樹脂改質酚系樹脂、二環戊二烯苯酚加成型樹脂、苯酚芳烷基樹脂(ZYLOCK樹脂)、由以間苯二酚酚醛清漆樹脂為代表之多羥基化合物與甲醛所合成之多苯酚酚醛清漆樹脂、萘酚芳烷基樹脂、三羥甲基甲烷樹脂、四酚基乙烷樹脂、萘酚酚醛清漆樹脂、萘酚-苯酚共縮酚醛清漆樹脂、萘酚-甲酚共縮酚醛清漆樹脂、聯苯改質酚系樹脂(利用雙亞甲基連結有苯酚核之多酚化合物)、聯苯改質萘酚樹脂(利用雙亞甲基連結有苯酚核之多萘酚化合物)、胺基三改質酚系樹脂(利用三聚氰胺、苯胍等連結有苯酚核之多酚化合物)或含烷氧基之芳香環改質酚醛清漆樹脂(利用甲醛連結有苯酚核及含烷氧基之芳香環之多酚化合物)等多酚化合物。
其等硬化劑可單獨地使用,亦可併用兩種以上。
又,本發明之組成物可單獨使用硬化促進劑,或者將硬化促進劑與上述之硬化劑進行併用。可使用會促進硬化性樹脂之硬化反應之各 種化合物作為硬化促進劑,例如可列舉:磷系化合物、三級胺化合物、咪唑化合物、有機酸金屬鹽、路易斯酸、胺錯鹽等。其中,較佳為使用咪唑化合物、磷系化合物、三級胺化合物,尤其是於用作半導體密封材料用途之情形時,就硬化性、耐熱性、電特性、耐濕可靠性等優異之方面而言,磷系化合物較佳為三苯基膦、四對甲苯基硼酸四苯基鏻,三級胺較佳為1,8-二氮雜雙環-[5.4.0]-十一烯(DBU)。
<其他摻合物>
本發明之組成物亦可具有其他摻合物。例如可列舉:觸媒、聚合起始劑、無機顏料、有機顏料、體質顏料、黏土礦物、蠟、界面活性劑、穩定劑、流動調整劑、偶聯劑、染料、整平劑、流變控制劑、紫外線吸收劑、抗氧化劑、難燃劑、塑化劑等。
<硬化物>
使本發明之組成物硬化而獲得之硬化物由於為低線膨脹且高玻璃轉移溫度,且耐熱分解性優異,故而可較佳地用於耐熱構件或電子構件。硬化物之成形方法並無特別限定,可由組成物單獨地成形,亦可藉由與基材進行積層而製成積層體。
於使本發明之組成物硬化之情形時,只要能夠進行熱硬化即可。於熱硬化時,亦可使用公知慣用之硬化觸媒,但本發明之組成物藉由順丁烯二醯亞胺基與烯丙基之反應,即便不使用硬化觸媒亦可進行硬化。
於進行熱硬化之情形時,可藉由1次加熱進行硬化,亦可經多階段之加熱步驟進行硬化。
於使用硬化觸媒之情形時,例如可使用鹽酸、硫酸、磷酸等 無機酸類;對甲苯磺酸、磷酸單異丙酯、乙酸等有機酸類;氫氧化鈉或氫氧化鉀等無機鹼類;鈦酸四異丙酯、鈦酸四丁酯等鈦酸酯類;1,8-二氮雜雙環[5.4.0]十一烯-7(DBU)、1,5-二氮雜雙環[4.3.0]壬烯-5(DBN)、1,4-二氮雜雙環[2.2.2]辛烷(DABCO)、三-正丁基胺、二甲基苄胺、單乙醇胺、咪唑、1-甲基咪唑等各種含有鹼性氮原子之化合物類;四甲基銨鹽、四丁基銨鹽、二月桂基二甲基銨鹽等各種四級銨鹽類,且具有氯化物、溴化物、羧酸酯或氫氧化物等作為抗衡陰離子之四級銨鹽類;二乙酸二丁基錫、二辛酸二丁基錫、二月桂酸二丁基錫、二乙醯丙酮酸二丁基錫、辛酸錫或硬脂酸錫等錫羧酸鹽;過氧化苯甲醯、氫過氧化異丙苯、過氧化二異丙苯、過氧化月桂醯、過氧化二三級丁基、氫過氧化三級丁基、過氧化甲基乙基酮、過氧化苯甲酸三級丁酯、2,5-二甲基-2,5-二(過氧化三級丁基)己炔-3等有機過氧化物等。觸媒可單獨地使用,亦可併用2種以上。
又,本發明之含烯丙基之順丁烯二醯亞胺化合物由於具有碳-碳間雙鍵,故而亦可併用活性能量線硬化。於進行活性能量線硬化之情形時,只要將光聚合起始劑摻合於組成物中即可。作為光聚合起始劑,只要使用公知者即可,例如可較佳地使用選自由苯乙酮類、二苯乙二酮(benzil)縮酮類、二苯甲酮類所組成之群中之一種以上。作為上述苯乙酮類,可列舉:二乙氧基苯乙酮、2-羥基-2-甲基-1-苯基丙烷-1-酮、1-(4-異丙基苯基)-2-羥基-2-甲基丙烷-1-酮、4-(2-羥基乙氧基)苯基-(2-羥基-2-丙基)酮等。作為上述二苯乙二酮縮酮類,例如可列舉1-羥基環己基-苯基酮、二苯乙二酮二甲基縮酮等。作為上述二苯甲酮類,例如可列舉二苯甲酮、鄰苯甲醯基苯甲酸甲酯等。作為上述 安息香類等,例如可列舉:安息香、安息香甲醚、安息香異丙醚等。光聚合起始劑可單獨地使用,亦可併用2種以上。
於併用熱硬化與活性能量線硬化而進行硬化之情形時,可將加熱與活性能量線照射同時進行,亦可將加熱與活性能量線照射分開進行。例如可於進行活性能量線照射後進行熱硬化,亦可於熱硬化後進行活性能量線硬化。又,亦可將各硬化方法組合並進行2次以上,只要視用途,適當選擇硬化方法即可。
<積層體>
本發明之硬化物可藉由與基材進行積層而製成積層體。
作為積層體之基材,只要視用途適時使用金屬或玻璃等無機材料、或者塑膠或木材等有機材料等即可,可製成積層體之形狀,亦可為平板、片狀、或可具有三維結構之立體狀。可為整面或一部分具有曲率者等視目的之任意形狀。又,基材之硬度、厚度等亦無限制。又,亦可將本發明之硬化物作為基材,進一步積層本發明之硬化物。
於電路基板或半導體封裝基板等用途之情形時,較佳為積層金屬箔,作為金屬箔,可列舉銅箔、鋁箔、金箔、銀箔等,就加工性良好之方面而言,較佳為使用銅箔。
於本發明之積層體中,硬化物層可藉由直接塗佈或直接成形而形成於基材上,亦可積層已成形者。於直接塗佈之情形時,作為塗佈方法,並無特別限定,可列舉噴霧法、旋轉塗佈法、浸漬法、輥塗法、刮刀塗佈法、刮刀輥法、刮刀法、淋幕式塗佈法、狹縫式塗佈法、網版印刷法、噴墨法等。於直接成形之情形時,可列舉模內成形、嵌入成形、真空成形、 擠出層壓成形、加壓成形等。
於積層已成形之組成物之情形時,可於積層未硬化或半硬化之組成物層後進行硬化,亦可將使組成物完全硬化而成之硬化物層積層於基材上。
又,對於本發明之硬化物,可藉由塗佈可成為基材之前驅物並使之硬化而進行積層,亦可於使可成為基材之前驅物或本發明之組成物於未硬化或半硬化之狀態下接著於本發明之硬化物後進行硬化。作為可成為基材之前驅物,並無特別限定,可列舉各種硬化性樹脂組成物等。
<纖維強化樹脂>
本發明之組成物具有纖維質基質,於該纖維質基質為強化纖維之情形時,含有纖維質基質之組成物可用作纖維強化樹脂。
關於使組成物含有纖維質基質之方法,只要為無損本發明之效果之範圍,則無特別限定,可列舉:利用混練、塗佈、含浸、注入、壓接等方法將纖維質基質與組成物進行複合化之方法,可視纖維之形態及纖維強化樹脂之用途而適時選擇。
關於將本發明之纖維強化樹脂進行成形之方法,並無特別限定。若製造板狀之製品,則通常為擠出成形法,但藉由平面加壓亦可實現。此外,可使用擠出成形法、吹塑成形法、壓縮成形法、真空成形法、射出成形法等。又,若製造膜狀之製品,則除熔融擠出法以外,亦可使用溶液澆鑄法,於使用熔融成形方法之情形時,可列舉吹脹膜成形、澆鑄成形、擠出層壓成形、壓延成形、板材成形、纖維成形、吹塑成形、射出成形、旋轉成形、被覆成形等。又,於會因活性能量線而硬化之樹脂之情形時, 可使用利用活性能量線之各種硬化方法而製造硬化物。尤其是於將熱硬化性樹脂設為基質樹脂之主成分之情形時,可列舉:將成形材料進行預浸體化並藉由加壓或高壓釜進行加壓加熱之成形法,除此以外,可列舉:RTM(Resin Transfer Molding,樹脂轉注)成形、VaRTM(Vaccum assist Resin Transfer Molding,真空輔助樹脂轉注)成形、積層成形、手工塗佈成形等。
<預浸體>
本發明之纖維強化樹脂可形成未硬化或半硬化之被稱為預浸體之狀態。亦可於預浸體之狀態下使製品流通,之後進行最終硬化而形成硬化物。於形成積層體之情形時,於形成預浸體後,積層其他層,之後進行最終硬化,藉此可形成密接有各層之積層體,故而較佳。
此時,作為所使用之組成物與纖維質基質之質量比例,並無特別限定,通常較佳為以預浸體中之樹脂分成為20~60質量%之方式進行調整。
<耐熱材料及電子材料>
本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物由於其硬化物為低線膨脹且耐熱分解性優異,故而可較佳地用於耐熱構件或電子構件。尤其是可較佳地用於半導體密封材、電路基板、增層膜、增層基板等、或者接著劑或抗蝕劑材料。又,亦可較佳地用於纖維強化樹脂之基質樹脂,作為高耐熱性之預浸體尤其適合。又,由於表現出對各種溶劑之溶解性,故而能夠進行塗料化,且與以往型之要求300℃以上之高溫燒繪之耐熱塗料相比,能夠於低溫下進行硬化,故而亦可較佳地用作耐熱塗料用樹脂。以上述方式獲得之耐熱構件或電子構件可較佳地用於各種用途,例 如可列舉:產業用機械零件、一般機械零件、汽車-鐵道-車輛等零件、航天-航空相關零件、電子-電氣零件、建築材料、容器‧包裝構件、生活用品、運動-娛樂用品、風力發電用殼體構件等,但並不限定於其等。
以下,對具代表性之製品,舉例進行說明。
1.半導體密封材料
作為由本發明之組成物獲得半導體密封材料之方法,可列舉如下方法:視需要,使用擠出機、捏合機、輥等,將上述組成物、及硬化促進劑、及無機填充劑等摻合劑充分地進行熔融混合直至變得均一。此時,作為無機填充劑,通常可使用熔融二氧化矽,但於用作功率電晶體、功率IC用高導熱半導體密封材之情形時,可將導熱率較熔融二氧化矽高之結晶二氧化矽、氧化鋁、氮化矽等進行高填充化、或者可使用熔融二氧化矽、晶質二氧化矽、氧化鋁、氮化矽等。關於其填充率,較佳為相對於硬化性樹脂組成物100質量份,以30~95質量%之範圍使用無機填充劑,其中,為了謀求難燃性或耐濕性或耐焊裂性之提高、線膨脹係數之降低,更佳為70質量份以上,進一步較佳為80質量份以上。
2.半導體裝置
作為由本發明之硬化性樹脂組成物獲得半導體裝置之半導體封裝成形,可列舉如下方法:使用澆鑄成型、或轉移成形機、射出成形機等將上述半導體密封材料進行成形,進一步於50~250℃加熱2~10小時。
3.印刷電路基板
作為由本發明之組成物獲得印刷電路基板之方法,可列舉如下方法:藉由慣例將上述預浸體進行積層,適當重疊銅箔,於1~10MPa之加壓下 以170~300℃進行10分鐘~3小時加熱壓接。
4.增層基板
關於由本發明之組成物獲得增層基板之方法,例如可列舉以下之步驟。首先,使用噴塗法、淋幕式塗佈法等將適當摻合有橡膠、填料等之上述組成物塗佈至形成有電路之電路基板上,之後進行硬化之步驟(步驟1)。然後,視需要進行特定之通孔部等之開孔後,藉由粗化劑進行處理,將其表面進行熱水洗,藉此形成凹凸,對銅等金屬進行鍍覆處理之步驟(步驟2)。視需要,將上述操作依序反覆進行,而將樹脂絕緣層及特定之電路圖案之導體層交替地增層而形成之步驟(步驟3)。再者,通孔部之開孔係於最外層之樹脂絕緣層之形成後進行。又,本發明之增層基板亦可藉由於170~300℃將於銅箔上已使該樹脂組成物半硬化之附樹脂之銅箔加熱壓接於形成有電路之配線基板上而形成粗化面,從而省略鍍覆處理之步驟而製作增層基板。
5.增層膜
作為由本發明之組成物獲得增層膜之方法,可藉由於作為基材之支持膜(Y)之表面塗佈上述組成物,進一步利用加熱、或熱風吹送等使有機溶劑乾燥而形成組成物之層(X)而進行製造。
作為此處所使用之有機溶劑,例如較佳為使用丙酮、甲基乙基酮、環己酮等酮類;乙酸乙酯、乙酸丁酯、乙酸賽路蘇、乙酸丙二醇單甲醚、卡必醇乙酸酯等乙酸酯類;賽路蘇、丁基卡必醇等卡必醇類;甲苯、二甲苯等芳香族烴類;二甲基甲醯胺、二甲基乙醯胺、N-甲基吡咯啶酮等,又,較佳為以不揮發分成為30~60質量%之比例使用。
關於所形成之層(X)之厚度,通常設為導體層之厚度以上。電路基板所具有之導體層之厚度為通常5~70μm之範圍,因此樹脂組成物層之厚度較佳為具有10~100μm之厚度。再者,本發明中之上述組成物層(X)亦可由下述之保護膜保護。藉由利用保護膜進行保護,可防止污物等對樹脂組成物層表面之附著或損傷。
上述之支持膜及保護膜可列舉:聚乙烯、聚丙烯、聚氯乙烯等聚烯烴、聚對酞酸乙二酯(以下有簡稱為「PET」之情況)、聚萘二甲酸乙二酯等聚酯、聚碳酸酯、聚醯亞胺、進一步脫模紙或銅箔、鋁箔等金屬箔等。再者,支持膜及保護膜除加速擴散處理、電暈處理以外,亦可實施脫模處理。支持膜之厚度並無特別限定,係於通常10~150μm、較佳為25~50μm之範圍內使用。又,保護膜之厚度較佳為設為1~40μm。
上述之支持膜(Y)係於層壓至電路基板上後,或藉由加熱硬化而形成絕緣層後被剝離。若於構成增層膜之硬化性樹脂組成物層加熱硬化後剝離支持膜(Y),則可防止於硬化步驟中之污物等之附著。於硬化後進行剝離之情形時,通常事先對支持膜實施脫模處理。
可使用以上述方式獲得之增層膜而製造多層印刷電路基板。例如於層(X)由保護膜保護之情形時,將其等剝離後,以將層(X)直接接觸於電路基板之方式於電路基板之單面或兩面藉由例如真空層壓法進行層壓。層壓之方法可為批次式,亦可為利用輥之連續式。又,亦可視需要,於進行層壓之前,視需要事先對增層膜及電路基板進行加熱(預熱)。關於層壓之條件,較佳為將壓接溫度(層壓溫度)設為70~140℃,較佳為壓接壓力設為1~11kgf/cm2(9.8×104~107.9×104N/m2),較佳為將空氣 壓設為20mmHg(26.7hPa)以下,於減壓下進行層壓。
6.導電膏
作為由本發明之組成物獲得導電膏之方法,例如可列舉:使導電性粒子分散於該組成物中之方法。上述導電膏可根據所使用之導電性粒子之種類,而作為電路連接用膏樹脂組成物或各向異性導電接著劑。
[實施例]
繼而,藉由實施例、比較例而對本發明具體地進行說明,但以下「份」及「%」只要沒有特別事先說明,則為質量基準。
再者,高效液相層析法(HPLC)、1H及13C-NMR、MS圖譜、示差掃描熱量測量(DSC)係於以下之條件下測量。
HPLC
裝置:安捷倫科技製造之「LC1260」
展開溶劑:示於下述表1中
檢測器:光電二極體陣列檢測器
流量:1.0mL/分鐘
使用管柱:Poroshell 120 EC-C18
1H-NMR
裝置:JEOL RESONANCE製造之「JNM-ECA600」
磁場強度:600MHz
累計次數:32次
溶劑:DMSO-d6
試樣濃度:30質量%
13C-NMR
裝置:JEOL RESONANCE製造之「JNM-ECA600」
磁場強度:150MHz
累計次數:320次
溶劑:DMSO-d6
試樣濃度:30質量%
FD-MS
裝置:日本電子股份有限公司製造「JMS-T100GC AccuTOF」
測量範圍:m/z=50.00~2000.00
變化率:25.6mA/min
最終電流值:40mA
陰極電壓:-10kV
DSC
裝置:Hitachi High-Tech Science公司製造之「X-DSC7000」
氣體氛圍:氮氣
升溫程式:30℃保持5分鐘→升溫速度10℃/分鐘→350℃保持2分鐘
<實施例1>含烯丙基之順丁烯二醯亞胺化合物A之合成
(1-1)胺基之保護
於安裝有溫度計、冷卻管、攪拌機之3L燒瓶中添加2,2-雙(3-胺基-4-羥基苯基)丙烷(BAPA,和歌山精化工業股份有限公司製造)150.21g(0.58mol)、DMF(N,N-二甲基甲醯胺)1L、及離子交換水0.45L並於室溫下進行攪拌。將反應液加熱至60℃後,慢慢地滴加乙酸酐148.22g(1.45mol)。滴加結束後,於60℃反應2小時後,空氣冷卻至室溫。將析出物進行過濾,利用離子交換水2L進行洗淨後,於80℃進行10小時真空乾燥,而獲得固體狀之反應物(a-1)177.21g(產率89.2%)。
(1-2)經取代或未經取代烯丙基之導入
於安裝有溫度計、冷卻管、攪拌機之3L燒瓶中添加反應物(a-1)150.00g(0.438mol)、丙酮2.2L並進行攪拌。繼而添加碳酸鉀133.79g(0.968mol),將反應液進行加熱而製成回流狀態。進行1小時回流後,歷時1小時滴加烯丙基溴116.60g(0.964mol)。滴加結束後,於回流下反應12小時後,空氣冷卻至室溫。進行過濾後,將反應液進行減壓濃縮,進一步於80℃進行10小時真空乾燥,而獲得反應物(a-2)177.88g(產率96.1%)。
(1-3)去保護
於安裝有溫度計、冷卻管、攪拌機之1L燒瓶中添加(a-2)170.00g(0.402mol)、乙醇330mL並進行攪拌。添加濃鹽酸108.97g並加熱至60℃。於60℃反應30小時後,空氣冷卻至室溫。利用20%氫氧化鈉水溶液將反應液中和後,利用乙酸乙酯400mL進行萃取。利用離子交換水200mL洗淨2次,添加硫酸鈉並進行乾燥後,進行減壓濃縮,將所獲得之反應物於80℃進行10小時真空乾燥,而獲得液狀之反應物(a-3)127.73g(產率93.8%)。
(1-4)順丁烯二醯亞胺化
於安裝有溫度計、冷卻管、迪安-斯塔克分離器(Dean-Stark Trap)、攪拌機之3L燒瓶中添加順丁烯二酸酐76.49g(0.780mol)、甲苯1.8L並於室溫下進行攪拌。繼而,歷時1小時滴加反應物(a-3)120.00g(0.355mol)與DMF 200mL之混合溶液。滴加結束後,於室溫下進行反應2小時。添加對甲苯磺酸一水合物9.82g,將加熱反應液並於回流下進行共沸流出之水與甲苯進行冷卻、分離後,僅使甲苯返回至系統內,進行脫水反應8小時。空氣冷卻至室溫後,進行減壓濃縮,而獲得褐色溶液274.58g。溶解於乙酸乙酯800mL中,利用離子交換水300mL洗淨3次,利用2%碳酸氫鈉水溶液300mL洗淨3次,添加硫酸鈉並進行乾燥後,進行減壓濃縮,將所獲得之反應物於80℃進行4小時真空乾燥,而獲得含有含烯丙基之順丁烯二醯亞胺化合物A之粗產物104.57g。所獲得之粗產物之純度為75.0%(HPLC面積%、檢測波長275nm)。
利用矽膠管柱層析法(展開溶劑:乙酸乙酯/己烷=55/45、體積比)對所獲得之粗產物進行分離精製,藉此獲得含烯丙基之順丁烯二醯亞胺化合物A 55.91g(產率31.5%)。再者,對所獲得之含烯丙基之順丁烯二醯亞胺化合物A之1H-NMR、13C-NMR、MS圖譜、DSC進行測量,又,測量HPLC而求出純度時,成為以下之結果。
1H-NMR:δ 7.22-7.16(8H),7.07-7.05(2H),5.94-5.84(2H),5.27-5.15(4H),4.54-4.51(4H),1.61(6H);13C-NMR:δ 169.97ppm,151.96ppm,142.39ppm,134.93ppm,133.19ppm,128.52ppm,128.09ppm,119.61ppm,116.65ppm,112.96ppm,68.26 ppm,41.27ppm,30.60ppm;MS圖譜:M+=498;熔點(DSC峰頂):134℃;純度:96.7%(HPLC面積%、檢測波長275nm)
[實施例2]含烯丙基之順丁烯二醯亞胺化合物B之合成
使用2,2-雙(3-胺基-4-羥基苯基)六氟丙烷(DAHF,五二化學工業股份有限公司製造)代替BAPA,除此以外,利用與實施例1相同之方法獲得含烯丙基之順丁烯二醯亞胺化合物B。再者,對所獲得之含烯丙基之順丁烯二醯亞胺化合物B之1H-NMR、13C-NMR、MS圖譜、DSC進行測量,又,測量HPLC而求出純度時,成為以下之結果。
1H-NMR:δ 7.34-7.28(6H),7.19(4H),5.97-5.87(2H),5.31-5.19(4H),4.63(4H); 13C-NMR:δ 169.57ppm,154.72ppm,135.04ppm,132.63ppm,131.91ppm,131.47ppm,123.61ppm,120.13ppm,117.18ppm,113.51ppm,68.52ppm;MS圖譜:M+=606;熔點(DSC峰頂):60℃;純度:97.4%(HPLC面積%、檢測波長275nm)
[實施例3]含烯丙基之順丁烯二醯亞胺化合物C之合成
依據Proceedings of the National Academy of Sciences,India,Section A:Physical Sciences,71(1),5-12;2001之文獻所記載之方法而合成4,4'-亞甲基雙(2-甲氧基苯胺)。
又,藉由以下之方法,由上述4,4'-亞甲基雙(2-甲氧基苯胺)合成5,5'-亞甲基雙(2-胺基苯酚)。更詳細而言,於安裝有溫度計、冷卻管、攪拌機之3L燒瓶中添加4,4'-亞甲基雙(2-甲氧基苯胺)60.00g(0.232mol)、乙酸800mL、氫溴酸(47%)800mL,一面進行攪拌一面進行加熱並設為回流狀態。於回流下反應12小時後,空氣冷卻至室溫。利用20%氫氧化鈉水溶液將反應液中和後,利用乙酸乙酯600mL進行萃取。利用離子交換水200mL洗淨3次,添加硫酸鈉並進行乾燥後,進行減壓濃 縮,而獲得5,5'-亞甲基雙(2-胺基苯酚)43.01g(產率80.5%)。
使用5,5'-亞甲基雙(2-胺基苯酚)代替BAPA,除此以外,利用與實施例1相同之方法獲得含烯丙基之順丁烯二醯亞胺化合物C。再者,對所獲得之含烯丙基之順丁烯二醯亞胺化合物C之1H-NMR、13C-NMR、MS圖譜、DSC進行測量,又,測量HPLC而求出純度時,成為以下之結果。
1H-NMR:δ 7.22-6.93ppm(8H),6.92ppm(2H),5.89ppm(2H),5.26-5.15ppm(4H),4.56ppm(4H),4.00ppm(2H);13C-NMR:δ 169.96ppm,153.92ppm,143.43ppm,134.96ppm,133.06ppm,130.31ppm,120.92ppm,118.17ppm,116.80ppm,113.91ppm,68.26ppm,41.07ppm;MS圖譜:M+=470;熔點(DSC峰頂):188℃;純度:93.0%(HPLC面積%、檢測波長275nm)
[實施例4]含烯丙基之順丁烯二醯亞胺化合物D之合成
使用4,4'-二胺基-3,3'-二羥基聯苯(HAB,和歌山精化工業股份有限公司製造)代替BAPA,除此以外,利用與實施例1相同之方法獲得含烯 丙基之順丁烯二醯亞胺化合物D。再者,對所獲得之含烯丙基之順丁烯二醯亞胺化合物D之1H-NMR、13C-NMR、MS圖譜、DSC進行測量,又,對HPLC測量而求出純度時,成為以下之結果。
1H-NMR:δ 7.42ppm(2H),7.38ppm(4H),7.24ppm(4H),5.99-5.90ppm(2H),5.32-5.19ppm(4H),4.72ppm(4H);13C-NMR:δ 169.91ppm,154.24ppm,142.05ppm,135.09ppm,133.14ppm,130.75ppm,119.87ppm,119.45ppm,116.83ppm,112.41ppm,68.41ppm;MS圖譜:M+=456;熔點(DSC峰頂):234℃;純度:98.3%(HPLC面積%、檢測波長254nm)
[比較例1]雙順丁烯二醯亞胺A之合成
於安裝有溫度計、冷卻管、迪安-斯塔克分離器、攪拌機之2L燒瓶中添加順丁烯二酸酐50.85g(0.519mol)、甲苯930mL並於室溫下進行攪拌。繼而,歷時1小時滴加4,4'-二胺基-2,2'-二甲基聯苯(m-TB,和歌山精化工業股份有限公司製造)50.09g(0.236mol)與DMF 110mL之混合溶液。滴加結束後,於室溫下進一步反應2小時。添加對甲苯磺酸一水合 物7.08g,將加熱反應液並於回流下共沸流出之水與甲苯進行冷卻、分離後,僅使甲苯返回至系統內,進行脫水反應22小時。空氣冷卻至室溫後,進行減壓濃縮,而獲得黃色之濕濾餅151.40g。溶解於DMF中,於離子交換水中進行再沈澱。將析出物進行過濾分離,利用離子交換水洗淨後,於80℃進行12小時真空乾燥,而獲得作為黃色粉末之雙順丁烯二醯亞胺A84.07g(產率95.8%)。再者,對所獲得之雙順丁烯二醯亞胺A之1H-NMR、13C-NMR、MS圖譜、DSC進行測量,又,測量HPLC而求出純度時,成為以下之結果。
1H-NMR:δ 7.31ppm(2H),7.24-7.21ppm(8H),2.07ppm(6H);13C-NMR:δ 170.01ppm,139.67ppm,136.10ppm,134.72ppm,130.74ppm,129.57ppm,127.97ppm,124.15ppm,19.58ppm;MS圖譜:M+=372;熔點(DSC峰頂):194℃;純度:91.6%(HPLC面積%、檢測波長254nm)
[比較例2]
作為比較例2,使用下述式所表示之BMI-1000(4,4'-二苯甲烷雙順丁烯二醯亞胺,大和化成工業股份有限公司製造)。
[評價]
使用實施例1~3之含烯丙基之順丁烯二醯亞胺化合物、以及比較例1及2之順丁烯二醯亞胺化合物進行各種評價。再者,於以下之評價中,將實施例1~3之含烯丙基之順丁烯二醯亞胺化合物、以及比較例1及2之順丁烯二醯亞胺化合物簡單地總稱為「順丁烯二醯亞胺化合物」。
<組成物及其硬化物>
製造含有順丁烯二醯亞胺化合物之組成物,使上述組成物硬化而製造硬化物。
針對所獲得之組成物,評價於150℃有無熔融及150℃熔融黏度。
又,針對所獲得之硬化物,評價玻璃轉移溫度、線膨脹係數、耐熱分解性。
(組成物及硬化物之製造)
依據下述表2進行摻合,而製造組成物1~12。又,針對所獲得之組成物1~12,藉由以下之條件進行硬化而製造硬化物1~12。
其中,關於組成物7、9、10,於製造硬化物時組成物一部分或全部未熔融。又,由於藉此無法製造硬化物7、9、10,故而無法評價玻璃轉移溫度、線膨脹係數、耐熱分解性。
硬化條件:於170℃加熱2小時,於200℃加熱2小時,於250℃加熱2小時
硬化物板厚度:2.4mm
(玻璃轉移溫度)
將製造所得之硬化物1~12(厚度:2.4mm)切成寬度5mm、長度54 mm之尺寸,將其作為試片。針對該試片,使用黏彈性測量裝置(DMA:Hitachi High-Tech Science公司製造之固體黏彈性測量裝置「DMS7100」,變形模式:雙夾持彎曲,測量模式:正弦波振動,頻率1Hz,升溫速度3℃/分鐘),將彈性模數變化變得最大(tanδ變化率最大)之溫度作為玻璃轉移溫度而進行評價。將所獲得之結果示於下述表3中。
(線膨脹係數)
將製造所得之硬化物1~12(厚度:2.4mm)切成寬度5mm、長度5mm之尺寸,將其作為試片。針對該試片,使用熱機械分析裝置(Hitachi High-Tech Science公司製造之「TMA/SS7100」,升溫速度:3℃/分鐘),測量40~60℃之範圍之膨脹率。將所獲得之結果示於下述表3中。
(耐熱分解性)
將製造所得之硬化物1~12(厚度:2.4mm)較細地剪裁,使用熱重量分析裝置(SII nanotechnology公司製造之「TG/DTA6200」),將升溫速度設為5℃/分鐘,於氮氣氛圍下進行測量,而求出5%重量減少之溫度(Td5)。將所獲得之結果示於下述表3中。
(接著力)
使製造所得之組成物0.2g於設置在銅板(古河電工公司製造,EFTEC-64T,厚度0.15mm)上之金屬製圓柱管(內徑:8mm、高度:10mm)中硬化。此時,硬化條件係於170℃加熱2小時,於200℃加熱2小時,於250℃加熱2小時。繼而,使用接合測試機裝置(RHESCA公司製造之「PTR-1102」,測量溫度:40℃,測量速度:0.10mm/sec),將銅板與塞滿硬化物之圓柱管產生剝離時之最大點應力作為接著力而進行評價。將所獲得之結果示於下述表4中。
<含纖維質基質之組成物及其硬化物>
製造含有順丁烯二醯亞胺化合物及作為纖維質基質之玻璃纖維之組成物,使上述組成物硬化而製造硬化物。
針對所獲得之硬化物,對彎曲模數、彎曲強度、彎曲應變進行評價。
(組成物及硬化物之製造)
依據下述表5進行摻合,而製造組成物13~22。此時,使用T-725H(適於成形材之玻璃纖維,日本電氣硝子股份有限公司製造)作為玻璃纖維。
又,關於所獲得之組成物13~22,藉由以下之條件進行硬化而製造硬化物13~22。
其中,關於組成物18、20、21,製造硬化物時組成物一部或全部未熔融,而無法製造硬化物18、20、21,因此無法評價彎曲模數、彎曲應變、彎曲強度。
硬化條件:於170℃加熱2小時,於200℃加熱2小時,於250℃加熱2小時
硬化物板厚度:2.4mm
(彎曲模數、彎曲應變、彎曲強度)
針對硬化物13~22,依據JIS-K6911:2006進行彎曲試驗,而測量彎曲模數、彎曲應變、彎曲強度。將所獲得之結果示於下述表6中。
<含填料之組成物>
製造含有順丁烯二醯亞胺化合物及作為填料之球狀二氧化矽之組成物。
針對所獲得之硬化物,對流動性進行評價。
(組成物之製造)
依據下述表7進行摻合,使用二輥機,於150℃之溫度下進行5分鐘熔融混練而製造組成物23~34。此時,使用作為球狀二氧化矽之FB-560(電氣化學股份有限公司製造)、作為矽烷偶合劑之KBM-403(γ-環氧丙氧基三乙氧基矽烷,信越化學工業股份有限公司製造)、作為巴西棕櫚蠟之PEARL WAX No.1-P(CERARICA NODA股份有限公司製造)。
(流動性)
將組成物注入至試驗用模具中,於175℃、70kg/cm2、120秒之條件 下測量螺旋流動值。此時,關於組成物29~34,若於175℃,則組成物未熔融,而無法測量螺旋流動值。將所獲得之結果示於下述表8中。
<含有分散介質之組成物及含有該組成物之硬化物之積層體>
製造含有順丁烯二醯亞胺化合物及作為有機溶劑之甲基乙基酮之組成物。
針對所獲得之積層體,評價介電常數、介電損耗正切、耐濕耐焊錫性。
(組成物及含有硬化物之積層體之製造)
依據下述表9進行摻合,而製造組成物35~46。此時,所獲得之組成物之不揮發分(N.V.)為58質量%。
又,針對所獲得之組成物35~46,藉由以下之條件進行硬化,而製造具有基材與含有硬化物之層之積層體35~46。
其中,關於組成物41~46,由於對甲基乙基酮之溶解性較差,而無法製造硬化物,故而無法評價介電常數、介電損耗正切、耐濕耐焊錫性。
基材:印刷配線基板用玻璃布「2116」(厚度:100μm,日東紡績股份有限公司製造)
重疊數:6
銅箔:TCR箔(厚度:18μm,日礦金屬股份有限公司製造)
預浸體化條件:160℃/2分鐘
硬化條件:200℃、2.9MPa、2小時
成形後板厚:0.8mm、樹脂量40%
(介電常數及介電損耗正切)
依據JIS C 6481:1999,藉由阻抗/材料分析儀「HP4291B」(安捷倫科技股份有限公司製造),對絕乾後在23℃、濕度50%之室內保管24小時後之積層體於1GHz之介電常數及介電損耗正切進行測量。將所獲得之結果示於下述表10中。
(耐濕耐焊錫性)
將積層體於85℃、85%RH之氛圍下放置168小時,進行吸濕處理。繼而,將進行過吸濕處理之積層體浸漬於260℃之焊浴中10秒鐘,利用目視確認有無產生龜裂。再者,評價係依據以下之基準進行。將所獲得之結果示於下述表10中。
○:未產生龜裂
×:產生龜裂
<含光聚合起始劑之組成物>
製造含有順丁烯二醯亞胺化合物及光聚合起始劑之組成物。
針對所獲得之組成物,評價硬化性。
(組成物之製造)
依據下述表11進行摻合,而製造組成物47~52。此時,使用Irgacure 907(2-甲基-1-[4-(甲硫基)苯基]-2-啉基(morpholino)-1-丙酮,BASF公司製造)作為光聚合起始劑。
其中,組成物50~52由於對作為光聚合起始劑之M-309(三羥甲基丙烷三丙烯酸酯(TMPTA),東亞合成股份有限公司製造)之相容性較差而無法製造組成物,故而無法評價硬化性。
(硬化性)
將組成物以厚度成為50μm之方式塗佈至玻璃基板上。繼而,自50mJ/cm2開始以每次10mJ/cm2之方式照射紫外線,測量塗膜表面變得不黏著為止之累計光量。將所獲得之結果示於表12中。
<含有分散介質之組成物>
製造含有順丁烯二醯亞胺化合物及作為有機溶劑之甲基乙基酮之組成物。
針對所獲得之組成物,評價造膜性。
(組成物之製造)
依據下述表13進行摻合,而製造組成物53~58。此時,所獲得之組成物之不揮發分(N.V.)為40質量%。
其中,關於組成物56~58,由於對甲基乙基酮之溶解性較差而無法製造組成物,故而無法評價造膜性。
(造膜性)
將組成物以硬化後之厚度成為20μm之方式塗佈於基材上,於250℃使之硬化2小時,利用目視觀察外觀,依據以下之基準進行評價。將所獲得之結果示於下述表14中。再者基材係使用標準之不鏽鋼板(SUS-304)。
○於基材表面形成有塗膜
×未造膜
[產業上之可利用性]
本發明之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物由於低熔點且其硬化物為低線膨脹而且耐熱分解性優異,故而可較佳地用於耐熱構件或電子構件。尤其是可較佳地用於半導體密封材、電路基板、增層膜、增層基板等、或者接著劑或抗蝕劑材料。又,亦可較佳地用於纖維強化樹脂之基質樹脂,而作為高耐熱性之預浸體尤其適合。進一步,由於表現出光硬化性,故而可較佳地用作各種光硬化成形材料,且由於表現出造膜性,故而可較佳地用作耐熱塗料用樹脂。
Claims (19)
- 一種組成物,含有申請專利範圍第1項之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物。
- 如申請專利範圍第2項之組成物,其進一步含有反應性化合物。
- 如申請專利範圍第2至4項中任一項之組成物,其進一步含有填料。
- 如申請專利範圍第2至4項中任一項之組成物,其進一步含有纖維質基質。
- 如申請專利範圍第5項之組成物,其進一步含有纖維質基質。
- 一種硬化物,其係使申請專利範圍第2至7項中任一項之組成物硬化而成。
- 一種積層體,具有基材與含有申請專利範圍第8項之硬化物之層。
- 如申請專利範圍第9項之積層體,其為增層(build-up)膜。
- 一種耐熱材料用組成物,含有申請專利範圍第2至7項中任一項之組成物。
- 一種耐熱構件,含有申請專利範圍第8項之硬化物。
- 一種電子材料用組成物,含有申請專利範圍第2至7項中任一項之組成物。
- 一種電子構件,含有申請專利範圍第8項之硬化物。
- 一種半導體密封材,含有申請專利範圍第2至7項中任一項之組成物。
- 一種預浸體,含有申請專利範圍第6或7項之組成物。
- 一種電路基板,具有申請專利範圍第16項之預浸體與銅箔層。
- 一種增層基板,具有申請專利範圍第10項之增層膜。
- 一種申請專利範圍第1項之含有經取代或未經取代烯丙基之順丁烯二醯亞胺化合物之製造方法,具有如下步驟:1-1)將具有2個苯環之含羥基之芳香族胺基化合物之胺基進行保護的步驟;1-2)向1-1)中所獲得之化合物之羥基導入經取代或未經取代烯丙基的步驟;1-3)自1-2)中所獲得之化合物之保護胺基進行去保護的步驟;及1-4)將1-3)中所獲得之化合物之胺基進行順丁烯二醯亞胺化的步驟。
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US11104788B2 (en) * | 2016-12-20 | 2021-08-31 | Dic Corporation | Composition, cured product and laminate |
JP7069618B2 (ja) * | 2017-09-28 | 2022-05-18 | Dic株式会社 | マレイミド化合物、並びにこれを用いた組成物および硬化物 |
TW201936578A (zh) * | 2018-02-28 | 2019-09-16 | 日商三菱瓦斯化學股份有限公司 | 化合物、樹脂、組成物及使用其之微影用膜形成材料 |
WO2020196829A1 (ja) * | 2019-03-27 | 2020-10-01 | 積水化学工業株式会社 | 樹脂材料及び多層プリント配線板 |
CN114127183A (zh) * | 2019-07-17 | 2022-03-01 | 松下知识产权经营株式会社 | 树脂组合物、预浸料、带树脂的膜、带树脂的金属箔、覆金属箔层压板以及布线板 |
TWI733541B (zh) * | 2019-08-09 | 2021-07-11 | 長春人造樹脂廠股份有限公司 | 含烯丙基樹脂及其應用 |
JP7433607B2 (ja) | 2019-12-18 | 2024-02-20 | Dic株式会社 | ガラス繊維含有樹脂組成物、及び、硬化物 |
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