TW202300487A - 硬化觸媒、樹脂組成物、密封材料、接著劑及硬化物 - Google Patents
硬化觸媒、樹脂組成物、密封材料、接著劑及硬化物 Download PDFInfo
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- TW202300487A TW202300487A TW111111928A TW111111928A TW202300487A TW 202300487 A TW202300487 A TW 202300487A TW 111111928 A TW111111928 A TW 111111928A TW 111111928 A TW111111928 A TW 111111928A TW 202300487 A TW202300487 A TW 202300487A
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- mercaptomethylthio
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- RQNVJDSEWRGEQR-UHFFFAOYSA-N tris(prop-2-enyl) borate Chemical compound C=CCOB(OCC=C)OCC=C RQNVJDSEWRGEQR-UHFFFAOYSA-N 0.000 description 1
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- RMKKVIHQXPFMFT-UHFFFAOYSA-N triundecyl borate Chemical compound B(OCCCCCCCCCCC)(OCCCCCCCCCCC)OCCCCCCCCCCC RMKKVIHQXPFMFT-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005491 wire drawing Methods 0.000 description 1
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Abstract
Description
本發明係關於一種硬化觸媒、樹脂組成物、密封材料、接著劑及硬化物。
單液型接著劑包含主劑及硬化觸媒,或包含主劑、硬化劑及硬化觸媒。硬化觸媒被認為是最影響接著劑的可使用時間及硬化條件。
目前市面上有多種用於單液型接著劑之硬化觸媒,主流為熱固性樹脂或熱塑性樹脂經胺等官能基修飾之類型(日本特開昭59-053526號公報;特開平3-177418號公報)、將胺系硬化觸媒以高分子殼包覆之類型(特開2000-080146號公報)、僅將環氧樹脂與咪唑加合之類型(特開昭60-004524號公報)。
本發明之目的係提供一種新穎的硬化觸媒、樹脂組成物、密封材料、接著劑及硬化物。
本發明之一實施態樣係具有下述結構式(I)之化合物的硬化觸媒。
[化學式1]
(I)
(式中,R
1為選自氫、苯基及C1~C17之烷基的基,R
2、R
3、R
5各自獨立為選自氫及C1~C6之烷基的基,R
4為選自氫、OH及OAc之基,n及m為整數,n及m之和為1以上且12以下或1以上且3以下)。
本發明之其他實施態樣係含有上述任一個硬化觸媒及熱固性樹脂之樹脂組成物。該熱固性樹脂可為環氧樹脂。該熱固性樹脂可為具有聚合性雙鍵基之化合物。樹脂組成物可另包含該熱固性樹脂的硬化劑。該硬化劑可為選自由含氧化合物、含氮化合物及硫醇化合物所組成之群組的一種。
本發明之另一實施態樣係含有上述任一個樹脂組成物之密封材料、接著劑或硬化物。
本發明之又一實施態樣係下述結構式(I)之化合物。
[化學式2]
(I)
(式中,R
1為選自苯基及C1~C17之烷基的基,R
2、R
3、R
5各自獨立為選自氫及C1~C6之烷基的基,R
4為選自OH及OAc之基,n及m為整數,n及m之和為1以上且12以下)。
上述式中,R
1可為選自苯基及C1~C10之烷基的基,R
2、R
3、R
5可為氫,R
4可為OH,n及m可為1。
與相關文獻之交互參照:本申請案係基於2021年3月30日申請之日本特許出願2021-058849主張優先權,藉由引用該基礎申請案而包含於本說明書。
發明之功效:藉由本發明,可提供一種新穎的硬化觸媒、樹脂組成物、密封材料、接著劑及硬化物。
根據本說明書的記載,發明所屬技術領域中具有通常知識者係明瞭本發明的目的、特徵、優點及其構思,發明所屬技術領域中具有通常知識者可容易地根據本說明書的記載重現本發明。以下記載之發明的實施形態及具體實施例等,係表示本發明的較佳實施態樣,用於例示及說明,不用以限定本發明。發明所屬技術領域中具有通常知識者係明瞭,在本說明書所揭示之本發明的意圖及範圍內,可基於本說明書的記載進行各種變更及修飾。
==化合物==
本實施形態之化合物為下述結構式(I)之化合物:
[化學式3]
(I)
(式中,R
1為選自苯基及C1~C17之烷基的基,R
2、R
3、R
5各自獨立為選自氫及C1~C6之烷基的基,R
4為選自OH及OAc之基,n及m為整數,n及m之和為1以上且12以下,較佳為6以下,更佳為3以下)。
R
1較佳為選自苯基及C1~C11之烷基。R
2、R
3、R
5較佳為氫。R
4較佳為OH。n及m分別較佳為1。
==硬化觸媒==
本實施形態之硬化觸媒含有具有下述結構式(I)之化合物。又,本說明書中,硬化觸媒(curing catalyst)意指在主劑自聚合或主劑與硬化劑聚合時,具有促進其聚合開始及/或進行之機能的觸媒。此外,硬化觸媒可能僅結合於聚合物的末端。
[化學式4]
(I)
(式中,R
1為選自氫、苯基及C1~C17之烷基的基,較佳為選自C1~C11之烷基的基,R
2、R
3、R
5各自獨立為選自氫及C1~C6之烷基的基,R
4為選自氫、OH及OAc之基,n及m為整數,n及m之和為1以上且12以下,較佳為6以下,更佳為3以下)。又較佳地,R
4為氫時,n及m之和為1,R
4為OH時,n及m之和亦為1。
該等化合物可使用實施例記載之方法及習知方法來容易地製造。
此硬化觸媒藉由具有鄰苯二甲醯亞胺骨架,在樹脂組成物中,不容易發生在非預料的溫度範圍內硬化觸媒溶解於樹脂,可使用時間延長,可作為熱固性樹脂的硬化觸媒。
本說明書揭示之硬化觸媒可含有一種或數種具有結構式(I)之化合物。又,亦可含有具有結構式(I)之化合物以外的一種或數種其他硬化觸媒。
==樹脂組成物==
本說明書揭示之樹脂組成物含有具有結構式(I)之硬化觸媒及樹脂。此樹脂組成物比含有習知硬化觸媒之樹脂組成物更安定,具有可使用時間長之特徵。
樹脂不特別限定,可為熱固性樹脂。具體而言,可舉例如環氧樹脂或具有聚合性雙鍵基之化合物(例如(甲基)丙烯酸基化合物或馬來醯亞胺化合物)。又,本說明書中,將丙烯酸基及甲基丙烯酸基統稱為(甲基)丙烯酸基。
(1)環氧樹脂
環氧樹脂不特別限定,可為單官能基環氧樹脂或多官能基環氧樹脂。
單官能基環氧樹脂為具有一個環氧基的環氧樹脂,作為反應性稀釋劑用於環氧樹脂組成物的黏度調整已為習知。單官能基環氧樹脂大致分為脂肪族單官能基環氧樹脂及芳香族單官能基環氧樹脂。由揮發性的觀點而言,單官能基環氧樹脂的環氧當量較佳為180~400 g/eq。
芳香族單官能基環氧樹脂可舉例如苯基環氧丙基醚、甲苯酚基環氧丙基醚、p-s-丁基苯基環氧丙基醚、苯基環氧乙烷、p-第三丁基苯基環氧丙基醚、o-苯基酚環氧丙基醚、m-苯基酚環氧丙基醚、p-苯基酚環氧丙基醚、N-環氧丙基鄰苯二甲醯亞胺等,但不限定於該等。該等之中,較佳為p-第三丁基苯基環氧丙基醚及苯基環氧丙基醚,特佳為p-第三丁基苯基環氧丙基醚。
脂肪族單官能基環氧樹脂可舉例如正丁基環氧丙基醚、2-乙基己基環氧丙基醚、α-環氧蒎烷、烯丙基環氧丙基醚、1-乙烯基-3,4-環氧環己烷、1,2-環氧基-4-(2-甲基環氧乙烷基)-1-甲基環己烷、1,3-雙(3-環氧丙氧基丙基)-1,1,3,3-四甲基二矽氧烷、新癸酸環氧丙基醚等,但不限定於該等。
多官能基環氧樹脂係指具有兩個以上環氧基之環氧樹脂。因此,本發明之樹脂組成物可包含二官能基環氧樹脂、三官能基環氧樹脂、四官能基環氧樹脂等。多官能基環氧樹脂大致分為脂肪族多官能基環氧樹脂及芳香族多官能基環氧樹脂。
脂肪族多官能基環氧樹脂可舉例如(聚)乙二醇二環氧丙基醚、(聚)丙二醇二環氧丙基醚、丁二醇二環氧丙基醚、新戊二醇二環氧丙基醚、1,6-己二醇二環氧丙基醚、三羥甲基丙烷二環氧丙基醚、聚四氫呋喃二環氧丙基醚、甘油二環氧丙基醚、新戊二醇二環氧丙基醚、環己烷型二環氧丙基醚、雙環戊二烯型二環氧丙基醚這樣的二環氧樹脂;三羥甲基丙烷三環氧丙基醚、甘油三環氧丙基醚這樣的三環氧樹脂;乙烯基(3,4-環己烯)二氧化物、2-(3,4-環氧基環己基)-5,1-螺-(3,4-環氧基環己基)-m-二噁烷這樣的脂環型環氧樹脂;四環氧丙基雙(胺基甲基)環己烷這樣的環氧丙基胺型環氧樹脂;1,3-二環氧丙基-5-甲基-5-乙基乙內醯脲這樣的乙內醯脲型環氧樹脂;及1,3-雙(3-環氧丙氧基丙基)-1,1,3,3-四甲基二矽氧烷這樣的具有矽氧骨架之環氧樹脂等,但不限定於該等。
上述例子中,「環己烷型二環氧丙基醚」係具有如此結構之化合物:兩個環氧丙基分別經由醚鍵結合至具有一個環己烷環作為母結構之二價飽和烴基。「雙環戊二烯型二環氧丙基醚」係具有如此結構之化合物:兩個環氧丙基分別經由醚鍵結合至具有雙環戊二烯骨架作為母結構之二價飽和烴基。又,環己烷型二環氧丙基醚特佳為環己烷二甲醇二環氧丙基醚。
芳香族多官能基環氧樹脂係具有包含苯環等芳香環結構之多官能基環氧樹脂。雙酚A型環氧樹脂等以往常用的環氧樹脂包含許多此種環氧樹脂。芳香族多官能基環氧樹脂可舉例如雙酚A型環氧樹脂;p-環氧丙基氧苯基二甲基參雙酚A二環氧丙基醚這樣的分支狀多官能基雙酚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;酚醛(novolac)型環氧樹脂;四溴基雙酚A型環氧樹脂;芴型環氧樹脂;聯苯芳烷基環氧樹脂;1,4-苯基二甲醇二環氧丙基醚這樣的二環氧樹脂;3,3',5,5'-四甲基-4,4'-二環氧丙基氧聯苯這樣的聯苯型環氧樹脂;二環氧丙基苯胺、二環氧丙基甲苯胺、三環氧丙基-p-胺酚、四環氧丙基-m-間苯二甲胺這樣的環氧丙基胺型環氧樹脂;及含萘環環氧樹脂等,但不限定於該等。
芳香族多官能基環氧樹脂較佳為雙酚F型環氧樹脂、雙酚A型環氧樹脂及環氧丙基胺型環氧樹脂,其中其環氧當量為90~200 g/eq者為佳。
(2)具有聚合性雙鍵基之化合物
具有聚合性雙鍵基之化合物不特別限定,較佳為具有乙烯基,特別是具有(甲基)丙烯醯基或馬來醯亞胺基作為反應性雙鍵基之高分子化合物。
(甲基)丙烯酸基化合物中,具有丙烯酸基之化合物可舉例如丙烯酸甲酯、甲基丙烯酸甲酯、丙烯酸乙酯、甲基丙烯酸乙酯、丙烯酸正丙酯、甲基丙烯酸正丙酯、丙烯酸異丙酯、甲基丙烯酸異丙酯、丙烯酸正丁酯、甲基丙烯酸正丁酯、丙烯酸正己酯、甲基丙烯酸正己酯、丙烯酸-2-乙基己酯、甲基丙烯酸-2-乙基己酯、丙烯酸正十二酯、甲基丙烯酸十二酯、丙烯酸十八酯、甲基丙烯酸十八酯等;具有脂環型烴基之化合物可舉例如丙烯酸環己酯、甲基丙烯酸環己酯、丙烯酸異莰酯、甲基丙烯酸異莰酯等;具有芳香基之乙烯系單體可舉例如苯乙烯、α-甲基苯乙烯、α-氯苯乙烯、乙烯基甲苯等;具有羥基之化合物可舉例如丙烯酸-2-羥基乙酯、甲基丙烯酸-2-羥基乙酯、丙烯酸-2-羥基丙酯、甲基丙烯酸-2-羥基丙酯、丙烯酸-3-羥基丙酯、甲基丙烯酸-3-羥基丙酯、丙烯酸-4-羥基丁酯、甲基丙烯酸-4-羥基丁酯、二乙二醇單丙烯酸酯、環己烷二甲醇單丙烯酸酯、環己烷二甲醇單甲基丙烯酸酯等;(甲基)丙烯醯胺類可舉例如丙烯醯胺、N-羥甲基丙烯醯胺、N-(甲氧基甲基)丙烯醯胺、N-(乙氧基甲基)丙烯醯胺、N-(異丁氧基甲基)丙烯醯胺、N-(丁氧基甲基)丙烯醯胺、甲基丙烯醯胺、N-羥甲基甲基丙烯醯胺、N-(甲氧基甲基)甲基丙烯醯胺、N-(乙氧基甲基)甲基丙烯醯胺、N-(異丁氧基甲基)甲基丙烯醯胺、N-(丁氧基甲基)甲基丙烯醯胺等。又,具有三個以上乙烯基之化合物可舉例如三羥甲基丙烷三丙烯酸酯、季戊四醇三丙烯酸酯、季戊四醇三丙烯酸酯、季戊四醇四丙烯酸酯、二三羥甲基丙烷四丙烯酸酯、二季戊四醇五丙烯酸酯、二季戊四醇六丙烯酸酯等多元醇衍生物之多官能基(甲基)丙烯酸酯;季戊四醇三烯丙酯、季戊四醇四烯丙酯、三羥甲基丙烷三烯丙酯等多官能基烯丙酯;ARONIX M-7100、ARONIX M-8030、ARONIX M-8060(均為東亞合成(股)製)等聚酯(甲基)丙烯酸酯;EO改質多官能基丙烯酸酯、PO改質多官能基丙烯酸酯、PETIA、PETRA、TMPTA、TMPEOTA、OTA480、EBECRYL12、EBECRYL40、EBECRYL140、DPHA(均為DAICEL Cytec(股)製)、ARONIX M-305、ARONIX M-309、ARONIX M-310、M-315、M-320、ARONIX M-350、ARONIX M-360、ARONIX M-370、ARONIX M-400、ARONIX M-402、ARONIX M-408、ARONIX M-450、(均為東亞合成(股)製)、NEOMER TA-401、TA-505、EA-301、DA-600(均為三洋化成工業(股)製)、NK ESTER A-TMPT、NK ESTER AD-TMP、NK ESTER A-TMPT-3EO、NK ESTER A-TMPT-9EO、NK ESTER A-TM-4E、NK ESTER A-TM-4P、NK ESTER TMPT-9EO、NK ESTER A-DPH、NK ESTER A-TMMT、NK ESTER A-9550、NK ESTER ATM-35E、NK ESTER TMPT(均為新中村化學工業(股)製)等聚醚(甲基)丙烯酸酯等。
具有馬來醯亞胺基之化合物可舉例如N,N’-(4,4’-二苯基甲烷)雙馬來醯亞胺、雙酚A二苯基醚雙馬來醯亞胺、3,3'-二甲基-5,5'-二乙基-4,4'-二苯基甲烷雙馬來醯亞胺、4-甲基-1,3-伸苯基雙馬來醯亞胺、1,6'-雙馬來醯亞胺-(2,2,4-三甲基)己烷、雙-(3-乙基-5-甲基-4-馬來醯亞胺苯基)甲烷、m-伸苯基雙馬來醯亞胺(N,N’-1,3-伸苯基雙馬來醯亞胺)、1,6-雙馬來醯亞胺己烷、1,2-雙馬來醯亞胺乙烷(N,N'-伸乙基二馬來醯亞胺)、N,N'-(1,2-伸苯基)雙馬來醯亞胺、N,N'-1,4-伸苯基二馬來醯亞胺、N,N'-(磺醯基二-p-伸苯基)二馬來醯亞胺、N,N'-[3,3'-(1,3-伸苯基二氧)二苯基]雙馬來醯亞胺等。又,亦可使用二聚物酸改質雙馬來醯亞胺。二聚物酸改質雙馬來醯亞胺可舉例如液狀雙馬來醯亞胺之BMI-689、BMI-1500、BMI-1700,或固體雙馬來醯亞胺之BMI-3000(均為Designer molecules公司製)。
<硬化劑>
本發明之樹脂組成物可包含一種或數種硬化劑。本發明之樹脂組成物可含有的硬化劑不特別限定,可舉例如胺及其衍生物等含氮化合物;羧酸末端聚酯、酸酐系、酚系硬化劑、雙酚A及甲酚酚醛樹脂、酚末端環氧樹脂等含氧化合物;硫醇化合物等含硫化合物。
胺及其衍生物等含氮化合物不特別限定,可舉例如三乙基四胺、四乙基五胺、m-間苯二甲胺、三甲基六亞甲基二胺、2-甲基五亞甲基二胺等脂肪族多胺、異佛爾酮二胺、1,3-雙胺基甲基環己烷、雙(4-胺基環己基)甲烷、降冰片烯二胺、1,2-二胺基環己烷等脂環型多胺、N-胺基乙基哌嗪、1,4-雙(2-胺基-2-甲基丙基)哌嗪等哌嗪型多胺、二乙基甲苯二胺、二甲基硫甲苯二胺、4,4’-二胺基-3,3’-二乙基二苯基甲烷、雙(甲基硫)甲苯二胺、二胺基二苯基甲烷、m-苯二胺、二胺基二苯基碸、二乙基甲苯二胺、三伸甲基雙(4-胺基苯甲酸酯)、聚四伸甲基氧-二-p-胺基苯甲酸酯等芳香族多胺類。市售品可舉例如Epikure-W、Epikure-Z(Yuka Shell Epoxy股份有限公司商品名)、jERCURE(登錄商標)-W、jERCURE(登錄商標)-Z(三菱化學股份有限公司商品名)、Kayahard A-A、Kayahard A-B、Kayahard A-S(日本化藥股份有限公司商品名)、Totoamine HM-205(新日鐵住金化學股份有限公司商品名)、ADEKA HARDENER EH-101(ADEKA股份有限公司商品名)、EPOMIK Q-640、EPOMIK Q-643(三井化學股份有限公司商品名)、DETDA80(Lonza公司商品名)、Totoamine HM-205(新日鐵住金化學股份有限公司商品名)等。
酸酐系硬化劑不特別限定,可舉例如甲基四氫鄰苯二甲酸酐、甲基六氫鄰苯二甲酸酐、烷基化四氫鄰苯二甲酸酐、甲基橋亞甲基四氫鄰苯二甲酸酐(methyl nadic anhydride)、經烯基取代之琥珀酸酐、戊二酸酐等。特佳為3,4-二甲基-6-(2-甲基-1-丙烯基)-1,2,3,6-四氫鄰苯二甲酸酐、1-異丙基-4-甲基-雙環[2,2,2]辛-5-烯-2,3-二羧酸酐、降冰片烷-2,3-二羧酸酐、甲基降冰片烷-2,3-二羧酸酐、氫化甲基橋亞甲基四氫鄰苯二甲酸酐、經烯基取代之琥珀酸酐、二乙基戊二酸酐。
酚系硬化劑係泛指具有酚性羥基之單體、寡聚物及聚合物,可舉例如酚醛樹脂及其烷基化物或烯丙基化物、甲酚酚醛樹脂、酚芳烷基(包含伸苯基、伸聯苯基骨架)樹脂、萘酚芳烷基樹脂、三酚甲烷樹脂、二環戊二烯型酚樹脂等。其中,較佳為烯丙基酚醛樹脂。
硫醇化合物包含水解性的多官能基硫醇化合物、非水解性的多官能基硫醇化合物。
水解性的多官能基硫醇化合物可舉例如三羥甲基丙烷參(3-巰基丙酸酯)(SC有機化學公司製:TMMP)、參-[(3-巰基丙醯基氧)-乙基]-異氰脲酸酯(SC有機化學公司製:TEMPIC)、季戊四醇肆(3-巰基丙酸酯)(SC有機化學公司製:PEMP)、三縮四乙二醇雙(3-巰基丙酸酯)(SC有機化學公司製:EGMP-4)、二季戊四醇陸(3-巰基丙酸酯)(SC有機化學公司製:DPMP)、季戊四醇肆(3-巰基丁酸酯)(昭和電工公司製:Karenz MT(登錄商標)PE1)、1,3,5-參(3-巰基丁醯基氧乙基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮(昭和電工公司製:Karenz MT(登錄商標)NR1)等。
非水解性的多官能基硫醇化合物可舉例如1,3,4,6-肆(2-巰基乙基)乙炔脲(商品名:TS-G,四國化成工業公司製)、1,3,4,6-肆(3-巰基丙基)乙炔脲(商品名:C3 TS-G,四國化成工業公司製)、1,3,4,6-肆(巰基甲基)乙炔脲、1,3,4,6-肆(巰基甲基)-3a-甲基乙炔脲、1,3,4,6-肆(2-巰基乙基)-3a-甲基乙炔脲、1,3,4,6-肆(3-巰基丙基)-3a-甲基乙炔脲、1,3,4,6-肆(巰基甲基)-3a,6a-二甲基乙炔脲、1,3,4,6-肆(2-巰基乙基)-3a,6a-二甲基乙炔脲、1,3,4,6-肆(3-巰基丙基)-3a,6a-二甲基乙炔脲、1,3,4,6-肆(巰基甲基)-3a,6a-二苯基乙炔脲、1,3,4,6-肆(2-巰基乙基)-3a,6a-二苯基乙炔脲、1,3,4,6-肆(3-巰基丙基)-3a,6a-二苯基乙炔脲、季戊四醇三丙烷硫醇(商品名:PEPT,SC有機化學製)、季戊四醇四丙烷硫醇等。
非水解性的多官能基硫醇化合物係亦可使用分子內具有兩個以上硫醚鍵之三官能基以上聚硫醇化合物。如此之硫醇化合物可舉例如1,2,3-參(巰基甲基硫)丙烷、1,2,3-參(2-巰基乙基硫)丙烷、1,2,3-參(3-巰基丙基硫)丙烷、4-巰基甲基-1,8-二巰基-3,6-二硫代辛烷、5,7-二巰基甲基-1,11-二巰基-3,6,9-三硫代十一烷、4,7-二巰基甲基-1,11-二巰基-3,6,9-三硫代十一烷、4,8-二巰基甲基-1,11-二巰基-3,6,9-三硫代十一烷、肆(巰基甲基硫甲基)甲烷、肆(2-巰基乙基硫甲基)甲烷、肆(3-巰基丙基硫甲基)甲烷、1,1,3,3-肆(巰基甲基硫)丙烷、1,1,2,2-肆(巰基甲基硫)乙烷、1,1,5,5-肆(巰基甲基硫)-3-硫代戊烷、1,1,6,6-肆(巰基甲基硫)-3,4-二硫代己烷、2,2-雙(巰基甲基硫)乙硫醇、3-巰基甲基硫-1,7-二巰基-2,6-二硫代庚烷、3,6-雙(巰基甲基硫)-1,9-二巰基-2,5,8-三硫代壬烷、3-巰基甲基硫-1,6-二巰基-2,5-二硫代己烷、1,1,9,9-肆(巰基甲基硫)-5-(3,3-雙(巰基甲基硫)-1-硫代丙基)3,7-二硫代壬烷、參(2,2-雙(巰基甲基硫)乙基)甲烷、參(4,4-雙(巰基甲基硫)-2-硫代丁基)甲烷、肆(2,2-雙(巰基甲基硫)乙基)甲烷、肆(4,4-雙(巰基甲基硫)-2-硫代丁基)甲烷、3,5,9,11-肆(巰基甲基硫)-1,13-二巰基-2,6,8,12-四硫代十三烷、3,5,9,11,15,17-陸(巰基甲基硫)-1,19-二巰基-2,6,8,12,14,18-六硫代十九烷、9-(2,2-雙(巰基甲基硫)乙基)-3,5,13,15-肆(巰基甲基硫)-1,17-二巰基-2,6,8,10,12,16-六硫代十七烷、3,4,8,9-肆(巰基甲基硫)-1,11-二巰基-2,5,7,10-四硫代十一烷、3,4,8,9,13,14-陸(巰基甲基硫)-1,16-二巰基-2,5,7,10,12,15-六硫代十六烷、8-[雙(巰基甲基硫)甲基]-3,4,12,13-肆(巰基甲基硫)-1,15-二巰基-2,5,7,9,11,14-六硫代十五烷、4,6-雙[3,5-雙(巰基甲基硫)-7-巰基-2,6-二硫代庚基硫]-1,3-二硫雜環己烷、4-[3,5-雙(巰基甲基硫)-7-巰基-2,6-二硫代庚基硫]-6-巰基甲基硫-1,3-二硫雜環己烷、1,1-雙[4-(6-巰基甲基硫)-1,3-二硫雜環己烷基硫]-1,3-雙(巰基甲基硫)丙烷、1-[4-(6-巰基甲基硫)-1,3-二硫雜環己烷基硫]-3-[2,2-雙(巰基甲基硫)乙基]-7,9-雙(巰基甲基硫)-2,4,6,10-四硫代十一烷、3-[2-(1,3-二硫雜環丁烷基)]甲基-7,9-雙(巰基甲基硫)-1,11-二巰基-2,4,6,10-四硫代十一烷、9-[2-(1,3-二硫雜環丁烷基)]甲基-3,5,13,15-肆(巰基甲基硫)-1,17-二巰基-2,6,8,10,12,16-六硫代十七烷、3-[2-(1,3-二硫雜環丁烷基)]甲基-7,9,13,15-肆(巰基甲基硫)-1,17-二巰基-2,4,6,10,12,16-六硫代十七烷等脂肪族聚硫醇化合物;4,6-雙[4-(6-巰基甲基硫)-1,3-二硫雜環己烷基硫]-6-[4-(6-巰基甲基硫)-1,3-二硫雜環己烷基硫]-1,3-二硫雜環己烷、4-[3,4,8,9-肆(巰基甲基硫)-11-巰基-2,5,7,10-四硫代十一烷基]-5-巰基甲基硫-1,3-二硫雜環戊烷、4,5-雙[3,4-雙(巰基甲基硫)-6-巰基-2,5-二硫代己基硫]-1,3-二硫雜環戊烷、4-[3,4-雙(巰基甲基硫)-6-巰基-2,5-二硫代己基硫]-5-巰基甲基硫-1,3-二硫雜環戊烷、4-[3-雙(巰基甲基硫)甲基-5,6-雙(巰基甲基硫)-8-巰基-2,4,7-三硫代辛基]-5-巰基甲基硫-1,3-二硫雜環戊烷、2-{雙[3,4-雙(巰基甲基硫)-6-巰基-2,5-二硫代己基硫]甲基}-1,3-二硫雜環丁烷、2-[3,4-雙(巰基甲基硫)-6-巰基-2,5-二硫代己基硫]巰基甲基硫甲基-1,3-二硫雜環丁烷、2-[3,4,8,9-肆(巰基甲基硫)-11-巰基-2,5,7,10-四硫代十一烷基硫]巰基甲基硫甲基-1,3-二硫雜環丁烷、2-[3-雙(巰基甲基硫)甲基-5,6-雙(巰基甲基硫)-8-巰基-2,4,7-三硫代辛基]巰基甲基硫甲基-1,3-二硫雜環丁烷、4-{1-[2-(1,3-二硫雜環丁烷基)]-3-巰基-2-硫代丙基硫}-5-[1,2-雙(巰基甲基硫)-4-巰基-3-硫代丁基硫]-1,3-二硫雜環戊烷等具有環結構之聚硫醇化合物。
<樹脂組成物的構成比例>
樹脂組成物中之硬化觸媒的比例不特別限定,相對於樹脂組成物中的熱固性樹脂,硬化觸媒的比例較佳為0.01~50wt%,更佳為0.01~30wt%,又較佳為0.01~20wt%。
樹脂組成物的增黏倍率到達初始之2倍為止的時間作為可使用時間,環氧-硫醇硬化系的可使用時間較佳為8小時以上,更佳為12小時以上,又較佳為16小時以上。關於其他硬化系,以安定性的觀點而言,較佳亦為可使用時間較長者。
<樹脂組成物的其他成分>
本發明之硬化性組成物除了主劑、硬化觸媒、硬化劑以外,可依需要含有例如下述者。
(1)安定劑
為了提升儲藏安定性並延長可使用時間,可對本發明之樹脂組成物添加安定劑。可使用習知的各種安定劑作為以環氧樹脂作為主劑之單液型接著劑的安定劑,較佳為選自由液狀硼酸酯化合物、鋁螯合物及有機酸所組成之群組的至少一種。
液狀硼酸酯化合物可舉例如2,2'-氧雙(5,5'-二甲基-1,3,2-氧硼雜環己烷)、三甲基硼酸酯、三乙基硼酸酯、三正丙基硼酸酯、三異丙基硼酸酯、三正丁基硼酸酯、三戊基硼酸酯、三烯丙基硼酸酯、三己基硼酸酯、三環己基硼酸酯、三辛基硼酸酯、三壬基硼酸酯、三癸基硼酸酯、三(十一基)硼酸酯、三(十六基)硼酸酯、三(十八基)硼酸酯、參(2-乙基己氧基)硼烷、雙(1,4,7,10-四氧雜十一基)(1,4,7,10,13-五氧雜四癸基)(1,4,7-三氧雜十一基)硼烷、三苯甲基硼酸酯、三苯基硼酸酯、三-o-甲苯基硼酸酯、三-m-甲苯基硼酸酯、三乙醇胺硼酸酯等。
鋁螯合物可使用例如鋁螯合物A(川研Fine Chemical股份有限公司製)。有機酸可使用例如巴比妥酸。
(2)填充劑
本發明之樹脂組成物可添加填充劑。填充劑的具體例子可舉出氧化矽填充劑、玻璃填充劑、氧化鋁填充劑、氧化鈦填充劑、氮化硼填充劑、氮化鋁填充劑、滑石填充劑、碳酸鈣填充劑、樹脂填充劑(例如、聚四氟乙烯(PTFE)填充劑、矽橡膠填充劑等)、銀、銅或鎳等導電性填充劑等。填充劑的形狀不特別限定,可為中空狀、球狀或非固定形狀。又,填充劑可為經表面處理者。
(3)耦合劑
本發明之樹脂組成物可添加耦合劑。耦合劑較佳為矽烷耦合劑,可使用環氧系、胺基系、乙烯基系、甲基丙烯酸基系、丙烯酸基系、巰基系等各種矽烷耦合劑。該等矽烷耦合劑可單獨使用一種或將兩種以上併用。
矽烷耦合劑例如為具有烯基之矽烷耦合劑,可舉出乙烯基三甲氧基矽烷(市售品可舉出信越化學工業公司製KBM-1003、Momentive Performance Materials Japan公司製A-171、Toray Dow Corning公司製Z-6300、旭化成Wacker Silicone公司製GENIOSIL XL10、日美商事公司製Sila-Ace S210等)、乙烯基三乙氧基矽烷(市售品可舉出信越化學工業公司製KBE-1003、Momentive Performance Materials Japan公司製A-151、Toray Dow Corning公司製Z-6519、旭化成Wacker Silicone公司製GENIOSIL GF56、日美商事公司製Sila-Ace S220等)、乙烯基三乙醯氧基矽烷(市售品可舉出旭化成Wacker Silicone公司製GENIOSIL GF62)、乙烯基參(2-甲氧基乙氧基)矽烷(市售品可舉出Momentive Performance Materials Japan公司製A-172)、乙烯基甲基二甲氧基矽烷(市售品可舉出Momentive Performance Materials Japan公司製A-2171、旭化成Wacker Silicone公司製GENIOSIL XL12等)、辛烯基三甲氧基矽烷(市售品可舉出信越化學工業公司製KBM-1083)、烯丙基三甲氧基矽烷(市售品可舉出Toray Dow Corning公司製Z-6825)、p-苯乙烯基三甲氧基矽烷(市售品可舉出信越化學工業公司製KBM-1403等)。具有丙烯酸基之矽烷耦合劑可舉例如3-丙烯醯氧基丙基三甲氧基矽烷、3-丙烯醯氧基丙基三乙氧基矽烷(市售品可舉出信越化學工業公司製KBM-5103等)等,具有甲基丙烯酸基之矽烷耦合劑可舉出3-甲基丙烯醯氧基丙基甲基二甲氧基矽烷(市售品可舉出信越化學工業公司製KBM-502、Toray Dow Corning公司製Z-6033等)、3-甲基丙烯醯氧基丙基三甲氧基矽烷(市售品可舉出信越化學工業公司製KBM-503、Momentive Performance Materials Japan公司製A-174、Toray Dow Corning公司製Z-6030、旭化成Wacker Silicone公司製GENIOSIL GF31、日美商事公司製Sila-Ace S710等)、3-甲基丙烯醯氧基丙基甲基二乙氧基矽烷(市售品可舉出信越化學工業公司製KBE-502)、3-甲基丙烯醯氧基丙基三乙氧基矽烷(信越化學工業公司製KBE-503、Momentive Performance Materials Japan公司製Y-9936)、甲基丙烯醯氧基辛基三甲氧基矽烷(信越化學工業公司製KBM-5803)等,具有環氧基之矽烷耦合劑可舉出2-(3,4-環氧環己基)乙基三甲氧基矽烷(市售品可舉出信越化學工業公司製KBM-303、Momentive Performance Materials Japan公司製A-186、Toray Dow Corning公司製Z-6043、日美商事公司製Sila-Ace S530等)、3-環氧丙氧基丙基甲基二甲氧基矽烷(市售品可舉出信越化學工業公司製KBM-402、Toray Dow Corning公司製Z-6044、日美商事公司製Sila-Ace S520等)、3-環氧丙氧基丙基三甲氧基矽烷(市售品可舉出信越化學工業公司製KBM-403、Momentive Performance Materials Japan公司製A-187、Toray Dow Corning公司製Z-6040、旭化成Wacker Silicone公司製GENIOSIL GF80、日美商事公司製Sila-Ace S510等)、3-環氧丙氧基丙基甲基二乙氧基矽烷(市售品可舉出信越化學工業公司製KBE-402)、3-環氧丙氧基丙基三乙氧基矽烷(市售品可舉出信越化學工業公司製KBE-403、Momentive Performance Materials Japan公司製A-1871、旭化成Wacker Silicone公司製GENIOSIL GF82等)、環氧丙氧基辛基三甲氧基矽烷(市售品可舉出信越化學工業公司製KBM-4803)等,具有胺基之矽烷耦合劑可舉出N-2-(胺基乙基)-3-胺基丙基甲基二甲氧基矽烷(信越化學工業公司製KBM-602、Momentive Performance Materials Japan公司製A-2120、旭化成Wacker Silicone公司製GENIOSIL GF-95、日美商事公司製Sila-Ace S310等)、N-2-(胺基乙基)-3-胺基丙基三甲氧基矽烷(市售品可舉出信越化學工業公司製KBM-603、Momentive Performance Materials Japan公司製A-1120、Momentive Performance Materials Japan公司製A-1122、Toray Dow Corning公司製Z-6020、Toray Dow Corning公司製Z-6094、旭化成Wacker Silicone公司製GENIOSIL GF-91、日美商事公司製Sila-Ace S320等)、3-胺基丙基三甲氧基矽烷(市售品可舉出信越化學工業公司製KBM-903、Momentive Performance Materials Japan公司製A-1110、Toray Dow Corning股份有限公司製Z-6610、日美商事公司製Sila-Ace S360等)、3-胺基丙基三乙氧基矽烷(市售品可舉出信越化學工業公司製KBE-903、Momentive Performance Materials Japan公司製A-1100、Toray Dow Corning公司製Z-6011、日美商事公司製Sila-Ace S330等)、3-三乙氧基矽基-N-(1,3-二甲基-亞丁基)丙胺(市售品可舉出信越化學工業公司製KBE-9103、日美商事公司製Sila-Ace S340等)、N-苯基-3-胺基丙基三甲氧基矽烷(市售品可舉出信越化學工業公司製KBM-573、Momentive Performance Materials Japan公司製Y-9669、Toray Dow Corning公司製Z-6883等)、N,N’-雙[3-(三甲氧基矽基)丙基]乙二胺(市售品可舉出日美商事公司製Sila-Ace XS1003)、N-(乙烯基苯甲基)-2-胺基乙基-3-胺基丙基三甲氧基矽烷之鹽酸鹽(市售品可舉出信越化學工業公司製KBM-575、Toray Dow Corning公司製Z-6032、日美商事公司製Sila-Ace S350等)等,具有異氰脲酸酯基之矽烷耦合劑可舉出參-(三甲氧基矽基丙基)異氰脲酸酯(市售品可舉出信越化學工業公司製KBM-9659),具有巰基之矽烷耦合劑可舉出3-巰基丙基甲基二甲氧基矽烷(市售品可舉出信越化學工業公司製KBM-802、Toray Dow Corning公司製Z-6852等)、3-巰基丙基三甲氧基矽烷(市售品可舉出信越化學工業公司製KBM-803、Momentive Performance Materials Japan公司製A-189、Toray Dow Corning公司製Z-6062、日美商事公司製Sila-Ace S810等)、3-巰基丙基三乙氧基矽烷(市售品可舉出Momentive Performance Materials Japan公司製A-1891、Toray Dow Corning公司製Z-6911)等,具有脲基之矽烷耦合劑可舉出3-脲基丙基三烷氧基矽烷(市售品可舉出信越化學工業公司製KBE-585)、3-脲基丙基三甲氧基矽烷、3-脲基丙基三乙氧基矽烷(市售品可舉出Momentive Performance Materials Japan公司製A-1160)等,具有硫醚基之矽烷耦合劑可舉出雙(三乙氧基矽基丙基)四硫醚,具有硫酯基之矽烷耦合劑可舉出3-辛醯基硫-1-丙基三乙氧基矽烷(市售品可舉出Momentive Performance Materials Japan公司製A-LINK599),具有異氰酸基之矽烷耦合劑可舉出3-異氰酸基丙基三乙氧基矽烷(市售品可舉出信越化學工業公司製KBE-9007、Momentive Performance Materials Japan公司製A-1310等)、3-異氰酸基丙基三甲氧基矽烷(市售品可舉出Momentive Performance Materials Japan公司製Y-5187、旭化成Wacker Silicone公司製GENIOSIL GF40等)等。
(4)其他添加劑
在不損害本發明目的之範圍內,對本發明之樹脂組成物可添加其他添加劑,例如碳黑、鈦黑、離子捕捉劑、整平劑、抗氧化劑、消泡劑、搖變劑、黏度調整劑、難燃劑、著色劑、溶劑等。各添加劑的種類、添加量係與一般方法相同。
=樹脂組成物的利用方法=
本說明書揭示之樹脂組成物作為單液型環氧樹脂,例如可用於電子零件用之密封材料或填充材料、點膠材料(dam)、導電性或絕緣性接著劑、晶片黏著材料、薄膜、塗覆劑、遮蔽材料等。亦可用於其他例如塗料、管線用材料、儲槽用材料等複合材料、地板材料、薄膜等土木建築材料、接著劑等,但利用方法不限於該等。
實施例:
==化合物的合成方法==
(化合物1)2-[2-羥基-3-(2-甲基-1H-咪唑-1-基)丙基]-1H-異吲哚-1,3(2H)-二酮之合成
[化學式5]
對已置入DMA(二甲基乙醯胺)(200 g)及磁攪拌子之反應容器,一邊攪拌一邊添加CUREZOL 2MZ-H(四國化成工業公司製,39.9 g、0.486 mol),加熱至60℃使其溶解。對所得到之溶液用約10分鐘緩慢添加DENACOL EX-731(Nagase ChemteX公司製,100 g、0.363 mmol)。全部溶解後,加熱至70℃,於相同溫度攪拌6小時。冷卻至常溫後,加入水(約200 mL)並攪拌,使結晶析出。將生成之固體抽氣過濾,以水清洗2次及以IPA清洗2次後,乾燥後得到化合物1(85.7 g)(回收率61%)。產物之物性測定值如下。
1H NMR(DMSO-d6): 7.89-7.78ppm (m, 4H), 7.05ppm (s, 1H), 6.67ppm (s, 1), 5.37ppm (d, 4.8Hz, 1H), 4.08-3.95ppm (m, 2H), 3.83 (dd, 8.6Hz, 15Hz, 1H), 3.62ppm (dd, 7.6Hz, 13.6Hz, 1H), 3.57ppm (dd, 4.8Hz, 13.6Hz,1H), 2.26ppm (s, 3H)
(化合物2)2-[2-羥基-3-(1H-咪唑-1-基)丙基]-1H-異吲哚-1,3(2H)-二酮(CAS編號:112086-61-0)之合成
[化學式6]
對已置入DMA(10 mL)之反應容器,一邊以攪拌子攪拌一邊添加CUREZOL SIZ(四國化成工業公司製,1.65 g、24.3 mmol),加熱至60℃使其溶解。對所得到之溶液用5分鐘緩慢添加DENACOL EX-731(Nagase ChemteX公司製,5.00 g、23.1 mmol)。全部溶解後,加熱至70℃,於相同溫度攪拌6小時。冷卻至常溫後,加入水(約15 mL)並於15℃攪拌,使結晶析出。將生成之固體抽氣過濾,以水清洗後,乾燥後得到固體之化合物2(3.69 g)。產物之物性測定值如下。
1H NMR (400 MHz DMSO-d6): 7.93-7.77ppm (m, 4H), 7.58ppm (s, 1H), 7.16ppm (s, 1H), 6.84ppm (s, 1H), 5.41ppm (d, 5.6 Hz), 4.11ppm (dd, 3.2Hz, 13.6Hz, 1H), 4.04-3.94ppm (m, 1H), 3.89ppm (dd, 7.2Hz, 14Hz, 1H), 3.60-3.47ppm (m, 2H)
(化合物3)2-[2-羥基-3-(2-苯基-1H-咪唑-1-基)丙基]-1H-異吲哚-1,3(2H)-二酮之合成
[化學式7]
對已置入DMA(10 mL)之反應容器,一邊以攪拌子攪拌一邊添加CUREZOL 2PZ-PW(四國化成工業公司製,3.50 g、24.3 mmol),加熱至60℃使其溶解。對所得到之溶液用5分鐘緩慢添加DENACOL EX-731(Nagase ChemteX公司製,5.00 g、23.1 mmol)。全部溶解後,加熱至70℃,於相同溫度攪拌23小時。冷卻至常溫後,加入水(約15 mL)並於15℃攪拌,使結晶析出。將生成之固體抽氣過濾,以水清洗後,乾燥後得到粗結晶4.04 g。
對粗結晶3.00 g添加0.5N鹽酸1.7 mL,以研缽磨碎,對所得到之粉體添加水形成懸濁液。將所得到之懸濁液抽氣過濾,使固體溶解於氯仿(約50 mL)並移至分液漏斗,將所得到之溶液以水-飽和小蘇打水-食鹽水依序清洗。將氯仿層以硫酸鈉脫水後,以液相分離濾紙(phase separator paper)過濾,將有機層以旋轉蒸發器濃縮。對所得到之橘色油狀物添加醋酸乙酯及己烷使其結晶化,將結晶抽氣過濾後減壓乾燥,藉此得到固體之化合物3(1.33 g)。產物之物性測定值如下。
1H NMR (400 MHz DMSO-d6) : 7.90-7.79ppm (m, 4H), 7.63-7.54ppm (m, 2H),7.39-7.26 (m, 4H), 6.97ppm (s, 1H), 5.54ppm (d, 5.6Hz, 1H), 4.17-3.92ppm (m, 3H), 3.57ppm (dd, 6.8Hz, 13.6Hz, 1H), 3.45ppm (dd, 5.6Hz, 13.6Hz, 1H)
(化合物4)2-[2-羥基-3-(2-十一基-1H-咪唑-1-基)丙基]-1H-異吲哚-1,3(2H)-二酮之合成
[化學式8]
對已置入DMA(15 mL)之反應容器,一邊以攪拌子攪拌一邊添加CUREZOL C11Z(四國化成工業公司製,5.14 g、24.3 mmol),加熱至60℃使其溶解。對所得到之溶液用5分鐘緩慢添加DENACOL EX-731(Nagase ChemteX公司製,5.00 g、23.1 mmol)。全部溶解後,加熱至70℃,於相同溫度攪拌23小時。冷卻至常溫後,加入水(約20 mL)並於15℃攪拌,使結晶析出。將生成之固體抽氣過濾,以水清洗後,乾燥後得到粗結晶5.70 g。
對粗結晶3.00 g添加1N鹽酸1.8 mL,以研缽磨碎,對所得到之粉體添加水形成懸濁液。將所得到之懸濁液抽氣過濾,使固體溶解於氯仿(約50 mL)並移至分液漏斗,將所得到之溶液以水-飽和小蘇打水-食鹽水依序清洗。將氯仿層以硫酸鎂脫水後,以液相分離濾紙(phase separator paper)過濾,將有機層以旋轉蒸發器濃縮。對所得到之白色固體添加醋酸乙酯及己烷使其形成懸濁液,將懸濁液抽氣過濾後,將所得到之結晶減壓乾燥,藉此得到化合物4(1.97 g)。產物之物性測定值如下。
1H NMR (400 MHz DMSO-d6): 7.91-7.81ppm (m, 4H), 7.04ppm (s, 1H), 6.70ppm (s, 1H), 5.37ppm (d, 5.6Hz, 1H), 4.05-3.93ppm (m, 2H), 3.82ppm (dd, 8.8Hz, 15.2Hz, 1H), 3.63ppm (dd, 7.8Hz, 14Hz, 1H), 3.53ppm (dd, 4.8Hz, 14Hz)
(化合物5)2-[2-(2-甲基-1H-咪唑-1-基)乙基]-1H-異吲哚-1,3(2H)-二酮
化合物5(CAS編號:858512-76-2)係使用市售品(由FCH Group公司購入)。
(化合物6)2-[2-(1H-咪唑-1-基)乙基]-1H-異吲哚-1,3(2H)-二酮
化合物6(CAS編號:72459-53-1)係使用市售品(由Enamine公司購入)。
將2-甲基-1H-咪唑(四國化成工業公司製,21.8 g、266 mmol)溶解於甲苯(78.7 mL)及甲醇(17.7 mL)之混合溶劑,加熱至80℃,將DENACOL EX-141(Nagase ChemteX公司製,22.0 g、147 mmol)之甲苯(38.1 mL)溶液用1小時滴下,之後,於相同溫度攪拌1小時。將所得到之溶液冷卻至室溫,於減壓下蒸餾去除溶劑,得到1-(2-甲基-1H-咪唑-1-基)-3-苯氧基丙-2-醇(47.85 g)之黃色固體。產物之鑑定係藉由
1H NMR進行,確認到已得到目的物。
(化合物8)2MZ-H
化合物8係使用市售品(由四國化成工業公司購入)。
==化合物的評價方法==
<測定熔點>
使用差示掃描量熱測定裝置(DSC 204 F1 Phoenix(登錄商標))(NETZSCH製)測定熔點。首先,在鋁盤上將各樹脂組成物計量5 mg,以鋁製蓋子密封後,在該蓋子的中心以針穿孔來準備測定樣品。接著,將此測定樣品於氮氣氣氛下(100 mL/分)、25℃~250℃之溫度範圍、升溫速度10℃/分之條件一邊升溫一邊測定熱流(mW/mg)。將圖表上得到波峰之溫度以解析軟體(NETZSCH Proteus-Thermal Analysis 版本8.0.2)算出,相當於熔點。
化合物的評價結果係如第1表所示。
ND:無法偵測
化合物 | 1 | 2 |
結構 | ||
熔點(℃) | 198 | 198 |
化合物 | 3 | 4 |
結構 | ||
熔點(℃) | 171 | 112 |
化合物 | 5 | 6 |
結構 | ||
熔點(℃) | 181 | 165 |
化合物 | 7 | 8 |
結構 | ||
熔點(℃) | ND | 149 |
==樹脂組成物的製作方法==
<實施例1~4、6、比較例1、2:環氧-硫醇硬化系>
將作為硬化觸媒之化合物1~4、7、8加入至環氧樹脂EXA835LV(DIC公司製)並混合。之後,以研缽磨碎至沒有凝集,使用行星式攪拌脫泡裝置於真空下進行攪拌及脫泡。在此,加入EXA835LV或者EXA835LV與CDMDG(昭和電工公司製)之混合物並混合。之後,使用行星式攪拌脫泡裝置於真空下進行攪拌及脫泡。再者,加入硫醇樹脂PEMP(SC有機化學公司製)並混合。之後,使用行星式攪拌脫泡裝置於真空下進行攪拌及脫泡,得到樹脂組成物。
<實施例5:環氧-硫醇硬化系>
對將EXA835LV與TS720(Cabot Specialty Chemicals公司製)以三根輥分散後之混合物,加入作為硬化觸媒之化合物1並混合。之後,以研缽磨碎至沒有凝集,使用行星式攪拌脫泡裝置於真空下進行攪拌及脫泡。在此,加入硫醇樹脂C3TSG(四國化成工業公司製)並混合。之後,使用行星式攪拌脫泡裝置於真空下進行攪拌及脫泡,得到樹脂組成物。
<實施例7、11、12:環氧均聚硬化系>
將作為硬化觸媒之化合物1、化合物5及化合物6加入至環氧樹脂EXA835LV並混合。之後,以研缽磨碎至沒有凝集,使用行星式攪拌脫泡裝置於真空下進行攪拌及脫泡,得到樹脂組成物。
<實施例8:環氧-酸酐硬化系>
將作為硬化觸媒之化合物1加入至環氧樹脂EXA835LV並混合。之後,以研缽磨碎至沒有凝集,使用行星式攪拌脫泡裝置於真空下進行攪拌及脫泡。在此,加入YDF8170(新日鐵住金化學公司製)並混合。之後,使用行星式攪拌脫泡裝置於真空下進行攪拌及脫泡。再者,加入酸酐樹脂YH306(三菱化學公司製)並混合。之後,以研缽磨碎至沒有凝集,使用行星式攪拌脫泡裝置於真空下進行攪拌及脫泡,得到樹脂組成物。
<實施例9:環氧-酚硬化系>
將作為硬化觸媒之化合物1加入至環氧樹脂EXA835LV並混合。之後,以研缽磨碎至沒有凝集,使用行星式攪拌脫泡裝置於真空下進行攪拌及脫泡。在此,加入EXA835LV並混合。之後,使用行星式攪拌脫泡裝置於真空下進行攪拌及脫泡。再者,加入酚樹脂MEH8005(明和化成公司製)並混合。之後,以研缽磨碎至沒有凝集,使用行星式攪拌脫泡裝置於真空下進行攪拌及脫泡,得到樹脂組成物。
<實施例10:丙烯酸基-硫醇硬化系>
將丙烯酸樹脂M7100(東亞合成公司製)、光自由基產生劑OMNIRAD184(IGM resins B.V.公司製)、阻聚劑Q-1301(富士軟片和光純藥公司製)、搖變劑TS720以三根輥分散,對所得到之混合物加入作為硬化觸媒之化合物1,再以三根輥分散。在此,加入PEMP並混合後,使用行星式攪拌脫泡裝置於真空下進行攪拌及脫泡,得到樹脂組成物。
==樹脂組成物的評價方法==
<測定可使用時間>
使用E型黏度計(TVE-25H:東機產業公司製,轉子名稱:3°×R9.7)於50rpm、25℃以預先設定之適當範圍(H、R或U)測定樹脂組成物的起始黏度。接著,於25℃、濕度50%之環境下,將保存於密閉容器之樹脂組成物放置4小時,作為可使用時間,將4小時以內未硬化者視為○,硬化者視為╳。之後,每4小時使用E型黏度計(TVE-25H:東機產業公司製,轉子名稱:3°×R9.7)於50rpm、25℃以預先設定之適當範圍(H、R或U)測定該樹脂組成物的黏度。然後,算出(放置各時間後的黏度)/(起始黏度)作為放置各時間後的增黏倍率。
<測定膠化時間(gel time)>
使用膠化試驗機(GT-D-15A:Yu-kari技研公司製)來測定膠化前的時間(稱為膠化時間)。將加熱板設於100℃、120℃或150℃,以試驗棒將樹脂組成物轉印至加熱板上。以試驗棒接觸樹脂組成物,達到牽絲狀態為止的時間作為膠化時間。
==結果==
上述樹脂組成物之各構成成分的分量及評價結果係整理在第2~3表。
第2表
UM:無法測量(斜線為未測量)
第3表
UM:無法測量(斜線為未測量)
實施例 | ||||||
實施例、比較例編號 | 1 | 2 | 3 | 4 | ||
材料 | 硬化觸媒 | 化合物1(wt%) | 1 | |||
化合物2(wt%) | 1 | |||||
化合物3(wt%) | 1 | |||||
化合物4(wt%) | 1 | |||||
化合物5(wt%) | ||||||
化合物6(wt%) | ||||||
化合物7(wt%) | ||||||
化合物8(wt%) | ||||||
環氧樹脂 | EXA835LV(wt%) | 57 | 57 | 57 | 57 | |
YDF8170(wt%) | ||||||
CDMDG(wt%) | ||||||
硫醇樹脂 | PEMP(wt%) | 42 | 42 | 42 | 42 | |
C3TSG(wt%) | ||||||
酸酐樹脂 | YH306(wt%) | |||||
酚樹脂 | MEH8005(wt%) | |||||
丙烯酸樹脂 | M7100(wt%) | |||||
自由基產生劑 | OMNIRAD-184(wt%) | |||||
阻聚劑 | Q-1301(wt%) | |||||
搖變劑 | TS720(wt%) | |||||
評價結果 | 增黏倍率(倍) | 4小時後 | 1.01 | 1.03 | 1.02 | |
8小時後 | 1.03 | 1.09 | 1.04 | |||
12小時後 | 1.11 | 1.51 | 1.12 | |||
16小時後 | 1.55 | 23.49 | 1.24 | |||
20小時後 | 42.49 | UM | 2.16 | |||
24小時後 | 1.9 | UM | UM | UM | ||
可使用時間 | ○ | ○ | ○ | ○ | ||
100℃膠化時間(秒) | 125 | 174 | 200 | 205 | ||
硬化觸媒的熔點(℃) | 198 | 198 | 171 | 113 |
實施例 | 比較例 | |||||
實施例、比較例編號 | 5 | 6 | 1 | 2 | ||
材料 | 硬化觸媒 | 化合物1(wt%) | 1 | 1 | ||
化合物2(wt%) | ||||||
化合物3(wt%) | ||||||
化合物4(wt%) | ||||||
化合物5(wt%) | ||||||
化合物6(wt%) | ||||||
化合物7(wt%) | 1 | |||||
化合物8(wt%) | 1 | |||||
環氧樹脂 | EXA835LV(wt%) | 57 | 27 | 57 | 57 | |
YDF8170(wt%) | ||||||
CDMDG(wt%) | 27 | |||||
硫醇樹脂 | PEMP(wt%) | 45 | 42 | 42 | ||
C3TSG(wt%) | 39 | |||||
酸酐樹脂 | YH306(wt%) | |||||
酚樹脂 | MEH8005(wt%) | |||||
丙烯酸樹脂 | M7100(wt%) | |||||
自由基產生劑 | OMNIRAD-184(wt%) | |||||
阻聚劑 | Q-1301(wt%) | |||||
搖變劑 | TS720(wt%) | 3 | ||||
評價結果 | 增黏倍率(倍) | 4小時後 | 硬化 | 硬化 | ||
8小時後 | UM | UM | ||||
12小時後 | UM | UM | ||||
16小時後 | UM | UM | ||||
20小時後 | UM | UM | ||||
24小時後 | 1.0 | 1.15 | UM | UM | ||
可使用時間 | ○ | ○ | ╳ | ╳ | ||
100℃膠化時間(秒) | 198 | 198 | 24 | 87 | ||
硬化觸媒的熔點(℃) | 198 | 198 | 73 | 149 |
實施例 | |||||||||
實施例、比較例編號 | 7 | 8 | 9 | 10 | 11 | 12 | |||
材料 | 硬化觸媒 | 化合物1(wt%) | 12 | 1 | 1 | 1.4 | |||
化合物2(wt%) | |||||||||
化合物3(wt%) | |||||||||
化合物4(wt%) | |||||||||
化合物5(wt%) | 12 | ||||||||
化合物6(wt%) | 12 | ||||||||
化合物7(wt%) | |||||||||
化合物8(wt%) | |||||||||
環氧樹脂 | EXA835LV(wt%) | 88 | 6 | 57 | 88 | 88 | |||
YDF8170(wt%) | 53 | ||||||||
CDMDG(wt%) | |||||||||
硫醇樹脂 | PEMP(wt%) | 38.0 | |||||||
C3TSG(wt%) | |||||||||
酸酐樹脂 | YH306(wt%) | 40 | |||||||
酚樹脂 | MEH8005(wt%) | 42 | |||||||
丙烯酸樹脂 | M7100(wt%) | 57.0 | |||||||
自由基產生劑 | OMNIRAD-184(wt%) | 1.0 | |||||||
阻聚劑 | Q-1301(wt%) | 0.2 | |||||||
搖變劑 | TS720(wt%) | 2.4 | |||||||
評價結果 | 增黏倍率(倍) | 4小時後 | 0.63 | 1.23 | |||||
8小時後 | 1.36 | 1.66 | |||||||
12小時後 | 1.56 | 2.70 | |||||||
16小時後 | 1.78 | UM | |||||||
20小時後 | 1.99 | UM | |||||||
24小時後 | 1.0 | 1.84 | 2.46 | UM | 1.24 | 1.55 | |||
可使用時間 | ○ | ○ | ○ | ○ | ○ | ○ | |||
膠化時間(秒) | 100℃ | 170 | |||||||
120℃ | 286 | 467 | |||||||
150℃ | 28 | 80 | 259 | ||||||
實施例所使用之硬化觸媒的熔點比比較例之硬化觸媒高。比較例2雖為高熔點,但分子量小,故容易溶解於環氧樹脂而缺乏安定性。比較樹脂組成物的可使用時間可知,相較於比較例在4小時即已硬化,實施例中,增黏倍率要達到2倍均花費8小時以上。
實施例之樹脂組成物在10分鐘以內膠化,具有充分的反應性及硬化性。
像這樣,本發明之硬化觸媒藉由具有鄰苯二甲醯亞胺骨架,係結晶性高,與習知的環氧樹脂與咪唑衍生物加合之加合物相比具有高熔點,又,藉由本發明之硬化觸媒,可得到樹脂組成物係安定且不容易發生在非預料的溫度範圍內硬化觸媒溶解於樹脂。
無
[第1圖] 實施例及比較例所使用之化合物的結構式。
Claims (12)
- 如請求項1之硬化觸媒,其中,n及m之和為3以下。
- 一種樹脂組成物,含有如請求項1或2之硬化觸媒及熱固性樹脂。
- 如請求項3之樹脂組成物,其中,該熱固性樹脂為環氧樹脂。
- 如請求項4之樹脂組成物,其中,該熱固性樹脂為具有聚合性雙鍵基之化合物。
- 如請求項4或5之樹脂組成物,另包含該熱固性樹脂的硬化劑。
- 如請求項4至6中任一項之樹脂組成物,其中,該硬化劑為選自由含氧化合物、含氮化合物及硫醇化合物所組成之群組的一種。
- 一種密封材料,含有如請求項3至7中任一項之樹脂組成物。
- 一種接著劑,含有如請求項3至7中任一項之樹脂組成物。
- 一種硬化物,係如請求項3至7中任一項之樹脂組成物的硬化物。
- 如請求項11之化合物,其中,R 1為選自苯基及C1~C10之烷基的基,R 2、R 3、R 5為氫,R 4為OH,n及m為1。
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