CN116745281A - 固化催化剂、树脂组合物、密封材料、粘接剂和固化物 - Google Patents
固化催化剂、树脂组合物、密封材料、粘接剂和固化物 Download PDFInfo
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- CN116745281A CN116745281A CN202280009235.XA CN202280009235A CN116745281A CN 116745281 A CN116745281 A CN 116745281A CN 202280009235 A CN202280009235 A CN 202280009235A CN 116745281 A CN116745281 A CN 116745281A
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- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
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- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
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- ZYMHKOVQDOFPHH-UHFFFAOYSA-N trimethoxy(oct-1-enyl)silane Chemical compound CCCCCCC=C[Si](OC)(OC)OC ZYMHKOVQDOFPHH-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
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- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
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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
- WAXLMVCEFHKADZ-UHFFFAOYSA-N tris-decyl borate Chemical compound CCCCCCCCCCOB(OCCCCCCCCCC)OCCCCCCCCCC WAXLMVCEFHKADZ-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
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Abstract
本发明的目的在于:提供新型的固化催化剂、树脂组合物、密封材料、粘接剂和固化物,本发明使用含有下述结构式(I)的化合物的固化催化剂。式中,R1为选自氢、苯基和C1~C17的烷基的基团,R2、R3、R5分别独立地为选自氢和C1~C6的烷基的基团,R4为选自氢、OH和OAc的基团,n和m为整数,n和m之和为1以上12以下。
Description
技术领域
本发明涉及固化催化剂、树脂组合物、密封材料、粘接剂和固化物。
背景技术
一液型粘接剂包含主剂和固化催化剂、或者主剂、固化剂和固化催化剂。固化催化剂被认为对粘接剂的有效期和固化条件的影响最大。
目前,市面上有多种用于一液型粘接剂的固化催化剂在销售,但是,主流产品是热固性树脂和热塑性树脂由胺等官能团改性的类型(日本特开昭59-053526号公报;日本特开平3-177418号公报)、胺系固化催化剂被高分子体的壳体覆盖的壳型(日本特开2000-080146号公报)和仅将环氧树脂和咪唑加成的类型(日本特开昭60-004524号公报)。
发明内容
发明所要解决的技术问题
本发明的目的在于:提供新型的固化催化剂、树脂组合物、密封材料、粘接剂和固化物。
用于解决技术问题的技术方案
本发明的一个实施方式是含有下述结构式(I)的化合物的固化催化剂。
式中,R1为选自氢、苯基和C1~C17的烷基的基团,
R2、R3、R5分别独立地为选自氢和C1~C6的烷基的基团,
R4为选自氢、OH和OAc的基团(Ac:乙酰基的缩写),n和m为整数,n和m之和为1以上12以下或1以上3以下。
本发明的另一实施方式是含有上述任一固化催化剂和热固性树脂的树脂组合物。上述热固性树脂可以是环氧树脂。上述热固性树脂可以是具有聚合性双键的化合物。还可以含有上述热固性树脂的固化剂。上述固化剂可以是选自含氧化合物、含氮化合物和硫醇化合物中之一。
本发明的又一实施方式是含有上述任一树脂组合物的密封材料、粘接剂或固化物。
本发明的再一实施方式是下述结构式(I)的化合物。
式中,R1为选自苯基和C1~C17的烷基的基团,
R2、R3、R5分别独立地为选自氢和C1~C6的烷基的基团,
R4为选自OH和OAc的基团,
n和m为整数,n和m之和为1以上12以下。
在上述式中,也可以是R1为选自苯基和C1~C10的烷基的基团,R2、R3、R5为氢,R4为OH,n和m为1。
==与相关文件的交叉引用==
本申请基于2021年3月30日提出的日本专利申请特愿2021-058849主张优先权,通过引用该基础申请将其内容援用于本说明书。
发明效果
根据本发明,能够提供新型的固化催化剂、树脂组合物、密封材料、粘接剂和固化物。
附图说明
图1是实施例和比较例中所使用的化合物的结构式。
具体实施方式
本领域技术人员可以基于本说明书的记载明确本发明的目的、特征、优点及其思想,根据本说明书的记载,本领域技术人员能够容易再现本发明。以下记载的本发明的实施方式和具体实施例等表示本发明的优选实施方式,用于举例或说明而表示,并非将本发明限定于此。在本说明书所公开的本发明的意图以及范围内,基于本说明书的记载能够进行各种改变和变更,这一点对于本领域技术人员而言是不言而喻的。
==化合物==
本实施方式的化合物是下述结构式(I)的化合物。
式中,R1为选自苯基和C1~C17的烷基的基团,
R2、R3、R5分别独立地为选自氢和C1~C6的烷基的基团,
R4为选自OH和OAc的基团,
n和m为整数,n和m之和为1以上、12以下,优选为6以下、更优选为3以下。
R1优选为选自苯基和C1~C11的烷基。R2、R3、R5优选为氢。R4优选为OH。n和m优选分别为1。
==固化催化剂==
本实施方式的固化催化剂含有具有下述结构式(I)的化合物。需要说明的是,在本说明书中,固化催化剂(curing catalyst)是指当主剂自聚合或主剂与固化剂聚合时具有促进其聚合的开始和/或进展的功能的催化剂。需要说明的是,固化催化剂有时仅被引入聚合物的末端。
式中,R1为选自氢、苯基和C1~C17、优选C1~C11的烷基的基团,R2、R3、R5分别独立地为选自氢和C1~C6的烷基的基团,R4为选自氢、OH和OAc的基团,n和m为整数,n和m之和为1以上、12以下,优选为6以下、更优选为3以下。
更优选R4为氢时,n和m之和为1,R4为OH时,n和m均为1。
这些化合物使用实施例记载的方法和已知方法,能够容易地制造。
该固化催化剂通过具有邻苯二甲酰亚胺骨架,在树脂组合物中,不易发生在非预期的温度范围内固化催化剂向树脂中溶解,延长了适用期,作为热固性树脂的固化催化剂有用。
本说明书所记载的固化催化剂可以含有一种或多种具有结构式(I)的化合物。此外,也可以含有具有结构式(I)的化合物以外的一种或多种其它固化催化剂。
==树脂组合物==
本说明书所记载的树脂组合物含有具有结构式(I)的固化催化剂和树脂。该树脂组合物具有比以往的含有固化催化剂的树脂组合物更稳定、有效期更长的特点。
树脂没有特别限定,优选为热固性树脂。具体可以列举环氧树脂、具有聚合性双键基的化合物(例如、(甲基)丙烯酰基化合物和马来酰亚胺化合物)。需要说明的是,在本说明书中,将丙烯酰基和甲基丙烯酰基统称记载为(甲基)丙烯酰基。
(1)环氧树脂
环氧树脂没有特别限定,可以是单官能环氧树脂,也可以是多官能环氧树脂。
单官能环氧树脂是具有一个环氧基的环氧树脂,一直以来作为反应性稀释剂用于环氧树脂组合物的粘度调节。单官能环氧树脂大致分为脂肪族单官能环氧树脂和芳香族单官能环氧树脂。从挥发性的观点考虑,单官能环氧树脂优选环氧当量为180~400g/eq。
作为芳香族单官能环氧树脂的例子,可以举出苯基缩水甘油醚、甲苯缩水甘油醚、对仲丁基苯基缩水甘油醚、苯基环氧乙烷、对叔丁基苯基缩水甘油醚、邻苯基苯酚缩水甘油醚、间苯基苯酚缩水甘油醚、对苯基苯酚缩水甘油醚、N-缩水甘油邻苯二甲酰亚胺等,但不限定于此。其中,优选为对叔丁基苯基缩水甘油醚和苯基缩水甘油醚,特别优选为对叔丁基苯基缩水甘油醚。
作为脂肪族单官能环氧树脂的例子,可以举出正丁基缩水甘油醚、2-乙基己基缩水甘油醚、α-氧化蒎烯、烯丙基缩水甘油醚、1-乙烯基-3,4-环氧环己烷、1,2-环氧-4-(2-甲基环氧乙烷基)-1-甲基环己烷、1,3-双(3-环氧丙氧基丙基)-1,1,3,3-四甲基二硅氧烷、新癸酸缩水甘油酯等,但不限于此。
多官能环氧树脂是指具有两个以上的环氧基的环氧树脂。因此,本发明的树脂组合物可以包含双官能环氧树脂、三官能环氧树脂、四官能环氧树脂等。多官能环氧树脂大致分为脂肪族多官能环氧树脂和芳香族多官能环氧树脂。
作为脂肪族多官能环氧树脂的例子,可以举出(聚)乙二醇二缩水甘油醚、(聚)丙二醇二缩水甘油醚、丁二醇二缩水甘油醚、新戊二醇二缩水甘油醚、1,6-己二醇二缩水甘油醚、三羟甲基丙烷二缩水甘油醚、聚四亚甲基醚乙二醇二缩水甘油醚、甘油二缩水甘油醚、新戊二醇二缩水甘油醚、环己烷型二缩水甘油醚、二环戊二烯型二缩水甘油醚之类的二环氧树脂;三羟甲基丙烷三缩水甘油醚、甘油三缩水甘油醚之类的三环氧树脂;乙烯基(3,4-环己烯)二氧化物、2-(3,4-环氧环己基)-5,1-螺-(3,4-环氧环己基)-间二噁烷之类的脂环式环氧树脂;四缩水甘油双(氨基甲基)环己烷之类的缩水甘油胺型环氧树脂;1,3-二缩水甘油基-5-甲基-5-乙基乙内酰脲之类的乙内酰脲型环氧树脂;1,3-双(3-环氧丙氧基丙基)-1,1,3,3-四甲基二硅氧烷之类的具有有机硅骨架的环氧树脂等,但不限于此。
在上述例中,“环己烷型二缩水甘油醚”是指具有以下结构的化合物,即,该结构为两个缩水甘油基各自通过醚键与具有一个环己烷环作为母体结构的二价饱和烃基键合而成的结构。“二环戊二烯型二缩水甘油醚”是指具有以下结构的化合物,即,该结构为两个缩水甘油基各自通过醚键与具有二环戊二烯骨架作为母体结构的二价饱和烃基键合而成的结构。另外,作为环己烷型二缩水甘油醚,特别优选为环己烷二甲醇二缩水甘油醚。
芳香族多官能环氧树脂是具有包含苯环等芳香环的结构的多官能环氧树脂。双酚A型环氧树脂等以往常用的环氧树脂中,这类树脂很多。作为芳香族多官能环氧树脂的例子,可以举出双酚A型环氧树脂;对缩水甘油氧基苯基二甲基三双酚A二缩水甘油醚之类的支链状多官能双酚A型环氧树脂;双酚F型环氧树脂;双酚E型环氧树脂;双酚S型环氧树脂;酚醛清漆型环氧树脂;四溴双酚A型环氧树脂;芴型环氧树脂;联苯芳烷基环氧树脂;1,4-苯基二甲醇二缩水甘油醚之类的二环氧树脂;3,3',5,5'-四甲基-4,4'-二缩水甘油氧基联苯之类的联苯型环氧树脂;二缩水甘油苯胺、二缩水甘油基甲苯胺、三缩水甘油基对氨基苯酚、四缩水甘油基间甲苯基二胺之类的缩水甘油胺型环氧树脂;以及含萘环的环氧树脂等,但不限于这些。
作为芳香族多官能环氧树脂,优选双酚F型环氧树脂、双酚A型环氧树脂和缩水甘油胺型环氧树脂,其中,优选环氧当量为90~200g/eq的环氧树脂。
(2)具有聚合性双键基的化合物
具有聚合性双键基的高分子化合物没有特别限制,优选具有乙烯基、特别是(甲基)丙烯酰基或马来酰亚胺基作为反应性双键基的高分子化合物。
在(甲基)丙烯酰基化合物中,例如作为具有烷基的化合物,可以举出丙烯酸甲酯、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、丙烯酸异丙酯、甲基丙烯酸异丙酯、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、丙烯酸正庚酯、甲基丙烯酸正庚酯、丙烯酸-2-乙基己酯、甲基丙烯酸-2-乙基己酯、丙烯酸正月桂酯、甲基丙烯酸月桂酯、丙烯酸硬脂酯、甲基丙烯酸硬脂酯等;作为具有脂环式烃基的化合物,可以举出丙烯酸环己酯、甲基丙烯酸环己酯、丙烯酸异冰片酯、甲基丙烯酸异冰片酯等;作为具有芳香族基团的乙烯基单体,可以举出苯乙烯、α-甲基苯乙烯、α-氯苯乙烯、乙烯基甲苯等;作为具有羟基的化合物,可以例示丙烯酸-2-羟乙酯、甲基丙烯酸-2-羟乙酯、丙烯酸-2-羟丙酯、甲基丙烯酸-2-羟丙酯、丙烯酸-3-羟丙酯、甲基丙烯酸-3-羟丙酯、丙烯酸-4-羟丁酯、甲基丙烯酸-4-羟丁酯、二乙二醇单丙烯酸酯、环己烷二甲醇单丙烯酸酯、环己烷二甲醇单甲基丙烯酸酯等;作为(甲基)丙烯酰胺类,可以举出丙烯酰胺、N-羟甲基丙烯酰胺、N-甲氧基甲基丙烯酰胺、N-乙氧基甲基丙烯酰胺、N-异丁氧基甲基丙烯酰胺、N-丁氧基甲基丙烯酰胺、甲基丙烯酰胺、N-羟甲基甲基丙烯酰胺、N-甲氧基甲基甲基丙烯酰胺、N-乙氧基甲基甲基丙烯酰胺、N-异丁氧基甲基甲基丙烯酰胺、N-丁氧基甲基甲基丙烯酰胺等。另外,作为具有3个以上乙烯基的化合物,可以例示三羟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、双三羟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的多官能(甲基)丙烯酸酯;季戊四醇三丙烯酸酯、季戊四醇四丙烯酸酯、三羟甲基丙烷三丙烯酸酯等多官能丙烯酸酯;Aronix M-7100、Aronix M-8030、Aronix M-8060(均为东亚合成株式会社制)等聚酯(甲基)丙烯酸酯;EO改性多官能丙烯酸酯、PO改性多官能丙烯酸酯、PETIA、PETRA、TMPTA、TMPEOTA、OTA480、EBECRYL12、EBECRYL40、EBECRYL140、DPHA(均为Daicel Sitech株式会社制)、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(均为东亚合成株式会社制)、Neomer TA-401、TA-505、EA-301、DA-600(均为三洋化成工业株式会社制)、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 ESTERA-TMMT、NK ESTER A-9550、NK ESTER ATM-35E、NK ESTER TMPT(均为新中村化学工业株式会社制)等聚醚(甲基)丙烯酸酯等。
作为具有马来酰亚胺基的化合物,例如可以举出N,N'-(4,4'-二苯基甲烷)双马来酰亚胺、双酚A二苯基醚双马来酰亚胺、3,3'-二甲基-5,5'-二乙基-4,4'-二苯基甲烷双马来酰亚胺、4-甲基-1,3-亚苯基双马来酰亚胺、1,6'-双马来酰亚胺基-(2,2,4-三甲基)己烷、双(3-乙基-5-甲基-4-马来酰亚胺苯基)甲烷、间亚苯基双马来酰亚胺(N,N'-1,3-亚苯基双马来酰亚胺)、1,6-双马来酰亚胺基己烷、1,2-双马来酰亚胺乙烷(N,N'-亚乙基二马来酰亚胺)、N,N'-(1,2-亚苯基)双马来酰亚胺、N,N'-1,4-亚苯基二马来酰亚胺、N,N'-(磺酰基二对亚苯基)二马来酰亚胺、N,N'-[3,3'-(1,3-亚苯基二氧基)二苯基]双马来酰亚胺等。另外,还可以使用二聚酸改性双马来酰亚胺。例如,作为二聚酸改性双马来酰亚胺,可以举出作为液态双马来酰亚胺的BMI-689、BMI-1500、BMI-1700、或作为固态双马来酰亚胺的BMI-3000(均为Designer molecules公司制)。
<固化剂>
本发明的树脂组合物可以含有一种或多种固化剂。
本发明的树脂组合物可以含有的固化剂没有特别限定,例如可以举出胺及其衍生物等含氮化合物;羧酸末端聚酯、酸酐系、酚系、双酚A以及甲酚酚醛清漆、酚末端环氧树脂等含氧化合物;硫醇化合物等含硫化合物。
胺及其衍生物等含氮化合物没有特别限定,可以例示三亚乙基四胺、四亚乙基五胺、间二甲苯二胺、三甲基六亚甲基二胺、2-甲基五亚甲基二胺等脂肪族多胺,异佛尔酮二胺、1,3-二氨基甲基环己烷、双(4-氨基环己基)甲烷、降冰片烯二胺、1,2-二氨基环己烷等脂环多胺,N-氨基乙基哌嗪、1,4-双(2-氨基-2-甲基丙基)哌嗪等哌嗪型多胺,二乙基甲苯二胺、二甲基硫代甲苯二胺、4,4'-二氨基-3,3'-二乙基二苯基甲烷、双(甲硫基)甲苯二胺、二氨基二苯基甲烷、间苯二胺、二氨基二苯砜、二乙基甲苯二胺、三亚甲基双(4-氨基苯甲酸酯)、聚四亚甲基氧二对氨基苯甲酸酯等芳香族多胺类等。作为市售品,可以举出EPICURE-W、EPICURE-Z(油化Shell Epoxy株式会社,商品名)、jERCURE(注册商标)-W、jERCURE(注册商标)-Z(三菱化学株式会社,商品名)、KAYAHARD A-A、KAYAHARD A-B、KAYAHARD A-S(日本化药株式会社,商品名)、Toto Amine HM-205(新日铁住金化学株式会社,商品名)、ADEKAHARDENER EH-101(株式会社ADEKA,商品名)、EOMIK Q-640、EOMIK Q-643(三井化学株式会社,商品名)、DETDA80(Lonza公司,商品名)、Toto Amine HM-205(新日铁住金化学株式会社,商品名)等。
酸酐系固化剂没有特别限定,例如可以举出甲基四氢邻苯二甲酸酐、甲基六氢邻苯二甲酸酐、烷基化四氢邻苯二甲酸酐、甲基降冰片烯二酸酐(methyl Himic anhydride)、取代有烯基的琥珀酸酐、戊二酸酐等。特别优选3,4-二甲基-6-(2-甲基-1-丙烯基)-1,2,3,6-四氢邻苯二甲酸酐、1-异丙基-4-甲基双环[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、氢化甲基纳迪克酸酐(hydrogenated methylNadic anhydride)、取代有烯基的琥珀酸酐、二乙基戊二酸酐。
酚系固化剂是指具有酚性羟基的单体、低聚物、聚合物全部,例如可以举出苯酚酚醛清漆树脂及其烷基化物或烯丙基化物、甲酚酚醛清漆树脂、苯酚芳烷基(包含亚苯基、联亚苯基骨架)树脂、萘酚芳烷基树脂、三酚甲烷树脂、二环戊二烯型酚醛树脂等。其中,优选烯丙基苯酚酚醛清漆树脂。
硫醇化合物包含水解性的多官能硫醇化合物、非水解性的多官能硫醇化合物。
作为水解性的多官能硫醇化合物的例子,可以举出三羟甲基丙烷三(3-巯基丙酸酯)(SC有机化学公司制:TMMP)、三[(3-巯基丙酰氧)乙基]异氰脲酸酯(SC有机化学公司制:TEMPIC)、季戊四醇四(3-巯基丙酸酯)(SC有机化学公司制:PEMP)、四乙二醇双(3-巯基丙酸酯)(SC有机化学公司制:EGMP-4)、二季戊四醇六(3-巯基丙酸酯)(SC有机化学公司制:DPMP)、季戊四醇四(3-巯基丁酸酯)(昭和电工公司制:KarenzMT(注册商标)PE1)、1,3,5-三(3-巯基丁酰氧乙基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮(昭和电工公司制:KarenzMT(注册商标)NR1)等。
作为非水解性多官能硫醇化合物的例子,可以举出1,3,4,6-四(2-巯基乙基)甘脲(商品名:TS-G,四国化成工业公司制)、(1,3,4,6-四(3-巯基丙基)甘脲(商品名:C3TS-G,四国化成工业公司制)、1,3,4,6-四(巯基甲基)甘脲、1,3,4,6-四(巯基甲基)-3a-甲基甘脲、1,3,4,6-四(2-巯基乙基)-3a-甲基甘脲、1,3,4,6-四(3-巯基丙基)-3a-甲基甘脲、1,3,4,6-四(巯基甲基)-3a,6a-二甲基甘脲、1,3,4,6-四(2-巯基乙基)-3a,6a-二甲基甘脲、1,3,4,6-四(3-巯基丙基)-3a,6a-二甲基甘脲、1,3,4,6-四(巯基乙基)-3a,6a-二苯基甘脲、1,3,4,6-四(2-巯基乙基)-3a,6a-二苯基甘脲、1,3,4,6-四(3-巯基丙基)-3a,6a-二苯基甘脲、季戊四醇三丙烷硫醇(商品名:PEPT,SC有机化学公司制)、季戊四醇四丙烷硫醇等。
作为非水解性多官能硫醇化合物,也可以使用分子内具有两个以上硫键的三官能以上的多硫醇化合物。作为这种硫醇化合物,例如可以举出1,2,3-三(巯基甲基硫代)丙烷、1,2,3-三(2-巯基乙基硫代)丙烷、1,2,3-三(3-巯基丙基硫代)丙烷、4-巯基甲基-1,8-二巯基-3,6-二硫杂辛烷、5,7-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、4,7-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、4,8-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、四(巯基甲基硫代甲基)甲烷、四(2-巯基乙基硫代甲基)甲烷、四(3-巯基丙基硫代甲基)甲烷、1,1,3,3-四(巯基甲基硫代)丙烷、1,1,2,2-四(巯基甲基硫代)乙烷、1,1,5,5-四(巯基甲基硫代)-3-硫杂戊烷、1,1,6,6-四(巯基甲基硫代)-3,4-二硫杂己烷、2,2-双(巯基甲基硫代)乙烷硫醇、3-巯基甲基硫代-1,7-二巯基-2,6-二硫杂庚烷、3,6-双(巯基甲基硫代)-1,9-二巯基-2,5,8-三硫杂壬烷、3-巯基甲基硫代-1,6-二巯基-2,5-二硫杂己烷、1,1,9,9-四(巯基甲基硫代)-5-(3,3-双(巯基甲基硫代)-1-硫杂丙基)3,7-二硫杂壬烷、三(2,2-双(巯基甲基硫代)乙基)甲烷、三(4,4-双(巯基甲基硫代)-2-硫杂丁基)甲烷、四(2,2-双(巯基甲基硫代)乙基)甲烷、四(4,4-双(巯基甲基硫代)-2-硫杂丁基)甲烷、3,5,9,11-四(巯基甲基硫代)-1,13-二巯基-2,6,8,12-四硫杂十三烷、3,5,9,11,15,17-六(巯基甲基硫代)-1,19-二巯基-2,6,8,12,14,18-六硫杂十九烷、9-(2,2-双(巯基甲基硫代)乙基)-3,5,13,15-四(巯基甲基硫代)-1,17-二巯基-2,6,8,10,12,16-六硫杂十七烷、3,4,8,9-四(巯基甲基硫代)-1,11-二巯基-2,5,7,10-四硫杂十一烷、3,4,8,9,13,14-六(巯基甲基硫代)-1,16-二巯基-2,5,7,10,12,15-六硫杂十六烷、8-[双(巯基甲基硫代)甲基]-3,4,12,13-四(巯基甲基硫代)-1,15-二巯基-2,5,7,9,11,14-六硫杂十五烷、4,6-双[3,5-双(巯基甲基硫代)-7-巯基-2,6-二硫杂庚基硫代]-1,3-二噻烷、4-[3,5-双(巯基甲基硫代)-7-巯基-2,6-二硫杂庚基硫代]-6-巯基甲基硫代-1,3-二噻烷、1,1-双[4-(6-巯基甲基硫代)-1,3-二噻烷基硫代]-1,3-双(巯基甲基硫代)丙烷、1-[4-(6-巯基甲基硫代)-1,3-二噻烷基硫代]-3-[2,2-双(巯基甲基硫代)乙基]-7,9-双(巯基甲基硫代)-2,4,6,10-四硫杂十一烷、3-[2-(1,3-二硫杂环丁基)]甲基-7,9-双(巯基甲基硫代)-1,11-二巯基-2,4,6,10-四硫杂十一烷、9-[2-(1,3-二硫杂环丁基)]甲基-3,5,13,15-四(巯基甲基硫代)-1,17-二巯基-2,6,8,10,12,16-六硫杂十七烷、3-[2-(1,3-二硫杂环丁基)]甲基-7,9,13,15-四(巯基甲基硫代)-1,17-二巯基-2,4,6,10,12,16-六硫杂十七烷等脂肪族多硫醇化合物;4,6-双[4-(6-巯基甲基硫代)-1,3-二噻烷基硫代]-6-[4-(6-巯基甲基硫代)-1,3-二噻烷基硫代]-1,3-二噻烷、4-[3,4,8,9-四(巯基甲基硫代)-11-巯基-2,5,7,10-四硫杂十一烷基]-5-巯基甲基硫代-1,3-二硫杂戊环、4,5-双[3,4-双(巯基甲基硫代)-6-巯基-2,5-二硫杂己基硫代]-1,3-二硫杂戊环、4-[3,4-双(巯基甲基硫代)-6-巯基-2,5-二硫杂己基硫代]-5-巯基甲基硫代-1,3-二硫杂戊环、4-[3-双(巯基甲基硫代)甲基-5,6-双(巯基甲基硫代)-8-巯基-2,4,7-三硫杂辛基]-5-巯基甲基硫代-1,3-二硫杂戊环、2-{双[3,4-双(巯基甲基硫代)-6-巯基-2,5-二硫杂己基硫代]甲基}-1,3-二硫杂环丁烷、2-[3,4-双(巯基甲基硫代)-6-巯基-2,5-二硫杂己基硫代]巯基甲基硫代甲基-1,3-二硫杂环丁烷、2-[3,4,8,9-四(巯基甲基硫代)-11-巯基-2,5,7,10-四硫杂十一烷基硫代]巯基甲基硫代甲基-1,3-二硫杂环丁烷、2-[3-双(巯基甲基硫代)甲基-5,6-双(巯基甲基硫代)-8-巯基-2,4,7-三硫杂辛基]巯基甲基硫代甲基-1,3-二硫杂环丁烷、4-{1-[2-(1,3-二硫杂环丁基)]-3-巯基-2-硫杂丙基硫代}-5-[1,2-双(巯基甲基硫代)-4-巯基-3-硫杂丁基硫代]-1,3-二硫杂戊环等具有环状结构的多硫醇化合物。
<树脂组合物的构成比例>
树脂组合物中的固化催化剂的比例没有特别限定,相对于树脂组合物中的热固性树脂,优选为0.01~50重量%、更优选为0.01~30重量%、进一步优选为0.01~20重量%。
以树脂组合物的增粘倍率直至达到初期的2倍的时间为适用期,环氧-硫醇固化系的适用期优选为8小时以上、更优选为12小时以上、进一步优选为16小时以上。其它固化系中,从稳定性的观点考虑,也优选适用期长。
<树脂组合物的其它成分>
本发明的固化组合物除了主剂、固化催化剂、固化剂以外,根据需要,例如还可以含有下述成分。
(1)稳定剂
在本发明的树脂组合物中,为了提高其贮存稳定性、延长适用期,可以添加稳定剂。作为以环氧树脂为主剂的一液型粘接剂的稳定剂,可以使用已知的各种稳定剂,优选为选自液态硼酸酯化合物、铝螯合物和有机酸中的至少一种。
作为液态硼酸酯化合物的例子,可以举出2,2'-氧基双(5,5'-二甲基-1,3,2-氧杂硼烷)、硼酸三甲酯、硼酸三乙酯、硼酸三正丙酯、硼酸三异丙酯、硼酸三正丁酯、硼酸三戊酯、硼酸三烯丙酯、硼酸三己酯、硼酸三环己酯、硼酸三辛酯、硼酸三壬酯、硼酸三癸酯、硼酸三(十二烷基)酯、硼酸三(十六烷基)酯、硼酸三(十八烷基)酯、三(2-乙基己氧基)硼烷、双(1,4,7,10-四氧杂十一烷基)(1,4,7,10,13-五氧杂十四烷基)(1,4,7-三氧杂十一烷基)硼烷、硼酸三苄酯、硼酸三苯酯、硼酸三邻甲苯酯、硼酸三间甲苯酯、硼酸三乙醇胺等。
作为铝螯合物,例如可以使用铝螯合物A(川研精细化学株式会社制)。作为有机酸,例如可以使用巴比妥酸。
(2)填充剂
本发明的树脂组合物可以添加填充剂。
作为填充剂的具体例,可以举出二氧化硅填料、玻璃填料、氧化铝填料、氧化钛填料、氮化硼填料、氮化铝填料、滑石填料、碳酸钙填料、树脂填料(例如聚四氟乙烯(PTFE)填料、有机硅橡胶填料等)、银、铜和镍等导电性填料等。形状没有特别限定,可以是中空状,也可以是球状,还可以是不定形。另外,填充剂也可以是经过表面处理的填充剂。
(3)偶联剂
本发明的树脂组合物可以添加偶联剂。作为偶联剂,优选硅烷偶联剂,可以使用环氧系、氨基系、乙烯基系、甲基丙烯酸系、丙烯酸系、巯基系等各种硅烷偶联剂。这些硅烷偶联剂可以单独使用,也可以并用两种以上。
作为硅烷偶联剂,例如,作为具有烯基的硅烷偶联剂,可以举出乙烯基三甲氧基硅烷(作为市售品,可以举出信越化学工业公司制KBM-1003、迈图高新材料日本公司制A-171、东丽道康宁公司制Z-6300、旭化成瓦克有机硅公司制GENIOSIL XL10、日美商事公司制Sila-Ace S210等)、乙烯基三乙氧基硅烷(作为市售品,可以举出信越化学工业公司制KBE-1003、迈图高新材料日本公司制A-151、东丽道康宁公司制Z-6519、旭化成瓦克有机硅制GENIOSIL GF56、日美商事公司制Sila-Ace S220等)、乙烯基三乙酰氧基硅烷(作为市售品,可以举出旭化成瓦克有机硅公司制GENIOSIL GF62)、乙烯基三(2-甲氧基乙氧基)硅烷(作为市售品,可以举出迈图高新材料日本公司制A-172)、乙烯基甲基二甲氧基硅烷(作为市售品,可以举出迈图高新材料日本公司制A-2171、旭化成瓦克有机硅公司制GENIOSIL XL12等)、辛烯基三甲氧基硅烷(作为市售品,可以举出信越化学工业公司制KBM-1083)、烯丙基三甲氧基硅烷(作为市售品,可以举出东丽道康宁公司制Z-6825)、对苯乙烯基三甲氧基硅烷(作为市售品,可以举出信越化学工业公司制KBM-1403等)。例如,作为具有丙烯酰基的硅烷偶联剂,可以举出3-丙烯酰氧基丙基三甲氧基硅烷、3-丙烯酰氧丙基三乙氧基硅烷(作为市售品,可以举出信越化学工业公司制KBM-5103等),作为具有甲基丙烯酰基的硅烷偶联剂,可以举出3-甲基丙烯酰氧基丙基甲基二甲氧基硅烷(作为市售品,可以举出信越化学工业公司制KBM-502,东丽道康宁公司制Z-6033等)、3-甲基丙烯酰氧基丙基三甲氧基硅烷(作为市售品,可以举出信越化学工业公司制KBM-503、迈图高新材料日本公司制A-174、东丽道康宁公司制Z-6030、旭化成瓦克有机硅公司制GENIOSIL GF31、日美商事公司制Sila-AceS710等)、3-甲基丙烯酰氧基丙基甲基二乙氧基硅烷(作为市售品,可以举出信越化学工业公司制KBE-502)、3-甲基丙烯酰氧基丙基三乙氧基硅烷(可以举出信越化学工业公司制KBE-503、迈图高新材料日本公司制Y-9936)、甲基丙烯酰氧基辛基三甲氧基硅烷(可以举出信越化学工业公司制KBM-5803)等,作为具有环氧基的硅烷偶联剂,可以举出2-(3,4-环氧环己基)乙基三甲氧基硅烷(作为市售品,可以举出信越化学工业公司制KBM-303、迈图高新材料日本公司制A-186、东丽道康宁公司制Z-6043、日美商事公司制Sila-Ace S530等)、3-环氧丙氧基丙基甲基二甲氧基硅烷(作为市售品,可以举出信越化学工业公司制KBM-402、东丽道康宁公司制Z-6044、日美商事公司制Sila-Ace S520等)、3-环氧丙氧基丙基三甲氧基硅烷(作为市售品,可以举出信越化学工业公司制KBM-403、迈图高新材料日本公司制A-187、东丽道康宁公司制Z-6040、旭化成瓦克有机硅公司制GENIOSIL GF80、日美商事公司制Sila-Ace S510等)、3-环氧丙氧基丙基甲基二乙氧基硅烷(作为市售品,可以举出信越化学工业公司制KBE-402)、3-环氧丙氧基丙基三乙氧基硅烷(作为市售品,可以举出信越化学工业公司制KBE-403、迈图高新材料日本公司制A-1871、旭化成瓦克有机硅公司制GENIOSILGF82等)、环氧丙氧基辛基三甲氧基硅烷(作为市售品,可以举出信越化学工业公司制KBM-4803)等,作为具有氨基的硅烷偶联剂,可以举出N-2-(氨基乙基)-3-氨基丙基甲基二甲氧基硅烷(可以举出信越化学工业公司制KBM-602、迈图高新材料日本公司制A-2120、旭化成瓦克有机硅公司制GENIOSIL GF-95、日美商事公司制Sila-Ace S310等)、N-2-(氨基乙基)-3-氨基丙基三甲氧基硅烷(作为市售品,可以举出信越化学工业公司制KBM-603、迈图高新材料日本公司制A-1120、迈图高新材料日本公司制A-1122、东丽道康宁公司制Z-6020、东丽道康宁公司制Z-6094、旭化成瓦克有机硅公司制GENIOSIL GF-91、日美商事公司制Sila-Ace S320等)、3-氨基丙基三甲氧基硅烷(作为市售品,可以举出信越化学工业公司制KBM-903、迈图高新材料日本制A-1110、东丽道康宁株式会社制Z-6610、日美商事公司制Sila-Ace S360等)、3-氨基丙基三乙氧基硅烷(作为市售品,可以举出信越化学工业公司制KBE-903、迈图高新材料日本公司制A-1100、东丽道康宁公司制Z-6011、日美商事公司制Sila-Ace S330等)、3-三乙氧基硅烷基-N-(1,3-二甲基亚丁基)丙胺(作为·BR>S售品,可以举出信越化学工业公司制KBE-9103、日美商事公司制Sila-Ace S340等)、N-苯基-3-氨基丙基三甲氧基硅烷(作为市售品,可以举出信越化学工业公司制KBM-573、迈图高新材料日本公司制Y-9669、东丽道康宁公司制Z-6883等)、N,N'-双[3-(三甲氧基硅烷基)丙基]乙二胺(作为市售品,可以举出日美商事公司制Sila-Ace XS1003)、N-(乙烯基苄基)-2-氨基乙基-3-氨基丙基三甲氧基硅烷的盐酸盐(作为市售品,可以举出信越化学工业公司制KBM-575、东丽道康宁公司制Z-6032、日美商事公司制Sila-Ace S350等)等,作为具有异氰脲酸酯基的硅烷偶联剂,可以举出三(三甲氧基硅烷基丙基)异氰脲酸酯(作为市售品,可以举出信越化学工业公司制KBM-9659),作为具有巯基的硅烷偶联剂,可以举出3-巯基丙基甲基二甲氧基硅烷(作为市售品,可以举出信越化学工业公司制KBM-802、东丽道康宁公司制Z-6852等)、3-巯基丙基三甲氧基硅烷(作为市售品,可以举出信越化学工业公司制KBM-803、迈图高新材料日本公司制A-189、东丽道康宁公司制Z-6062、日美商事公司制Sila-Ace S810等)、3-巯基丙基三乙氧基硅烷(作为市售品,可以举出迈图高新材料日本公司制A-1891、东丽道康宁公司制Z-6911)等,作为具有脲基的硅烷偶联剂,可以举出3-脲基丙基三烷氧基硅烷(作为市售品,可以举出信越化学工业公司制KBE-585)、3-脲基丙基三甲氧基硅烷、3-脲基丙基三乙氧基硅烷(作为市售品,可以举出迈图高新材料日本公司制A-1160)等,作为具有硫基的硅烷偶联剂,可以举出双(三乙氧基硅烷基丙基)四硫化物,作为具有硫酯基的硅烷偶联剂,可以举出3-辛酰硫代-1-丙基三乙氧基硅烷(作为市售品,可以举出迈图高新材料日本制A-LINK599),作为具有异氰酸酯基的硅烷偶联剂,可以举出3-异氰酸酯丙基三乙氧基硅烷(作为市售品,可以举出信越化学工业公司制KBE-9007、迈图高新材料日本公司制A-1310等)、3-异氰酸酯丙基三甲氧基硅烷(作为市售品,可以举出迈图高新材料日本公司制Y-5187,旭化成瓦克有机硅公司制GENIOSIL GF40等)等。
(4)其它添加剂
在无损于本发明的目的的范围内,本发明的树脂组合物可以添加其它添加剂、例如炭黑、钛黑、离子捕捉剂、流平剂、抗氧化剂、消泡剂、触变剂、粘度调节剂、阻燃剂、着色剂、溶剂等。各添加剂的种类、添加量可参考常规方法。
==树脂组合物的使用方法==
本说明书所记载的树脂组合物能够用于例如电子部件用的密封材料或填充材料、阻尼材料、导电性或绝缘性的粘接剂、芯片贴装材料、膜、涂层剂、屏蔽材料等。此外,还可以用于涂料、管用材料、釜用材料等的复合材料、地板材料、膜材等土木建筑材料、粘接剂等,但使用方法不限于此。
实施例
==化合物的合成方法==
(化合物1)2-[2-羟基-3-(2-甲基-1H-咪唑-1-基)丙基]-1H-异吲哚-1,3(2H)-二酮的合成
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向加入有DMA(二甲基乙酰胺)(200g)和磁力搅拌器的反应容器中,在搅拌状态下,加入CUREZOL 2MZ-H(四国化成工业公司制39.9g,0.486mol),加热至60℃使之溶解。用约10分钟向所得到的溶液中少量逐步加入了DENACOL EX-731(Nagase Chemtex公司制,100g,0.363mmol)。全部溶解后,加热至70℃,在该温度下搅拌了6小时。冷却至常温后,加水(约200mL)搅拌,使结晶析出。将所生成的固体抽滤,用水清洗两次,用IPA清洗两次,然后干燥,得到化合物1(85.7g)(回收率61%)。生成物的物性测定值如下所示。
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-羟基-3-(1H-咪唑-1-基)丙基]-1H-异吲哚-1,3(2H)-二酮(CAS登记号:112086-61-0)的合成
向加入有DMA(10mL)的反应容器中,在用搅拌器搅拌的状态下,加入CUREZOL SIZ(四国化成工业公司制,1.65g,24.3mmol),加热至60℃使之溶解。用约5分钟向所得到的溶液中少量逐步加入了DENACOL EX-731(Nagase Chemtex公司制,5.00g,23.1mmol)。全部溶解后,加热至70℃,在该温度下搅拌了6小时。冷却至常温后,加水(约15mL)在15℃的温度下搅拌,使结晶析出。将所生成的固体抽滤,用水清洗后,干燥,得到固体的化合物2(3.69g)。生成物的物性测定值如下所示。
1H NMR(400MHz DMSO-d6):7.93-7.77ppm(m,4H),7.58ppm(s,1H),7.16ppm(s,1H),6.84ppm(s,1H),5.41ppm(d,5.6Hz),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-羟基-3-(2-苯基-1H-咪唑-1-基)丙基]-1H-异吲哚-1,3(2H)-二酮的合成
向加入有DMA(10mL)的反应容器中,在用搅拌器搅拌的状态下,加入CUREZOL 2PZ-PW(四国化成工业公司制,3.50g,24.3mmol),加热至60℃使之溶解。用约5分钟向所得到的溶液中少量逐步加入了DENACOL EX-731(Nagase Chemtex公司制,5.00g,23.1mmol)。全部溶解后,加热至70℃,在该温度下搅拌了23小时。冷却至常温后,加水(约15mL)在15℃的温度下搅拌,使结晶析出。将所生成的固体抽滤,用水清洗后,干燥,得到粗结晶4.04g。
将1.7mL的0.5N盐酸加入到3.00g的粗结晶中,在乳钵中研碎,向所得到的粉体中加水,使其悬浊。对所得到的悬浊液进行吸滤,使固体溶解在氯仿(约50mL)中并移至分液漏斗,将所得到的溶液依次用水→饱和小苏打水→食盐水清洗。用硫酸钠将氯仿层脱水之后,用液相分离滤纸进行过滤,用旋转蒸发器将有机层浓缩。将乙酸乙酯和己烷加入到所得到的橙色油状物中使其结晶化,将结晶吸滤后,进行减压干燥,得到固体的化合物3(1.33g)。生成物的物性测定值如下所示。
1H NMR(400MHz DMSO-d6):7.90-7.79ppm(m,4H),7.63-7.54ppm(m,2H),7.39-7.26ppm(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-羟基-3-(2-十一烷基-1H-咪唑-1-基)丙基]-1H-异吲哚-1,3(2H)-二酮的合成
向加入有DMA(15mL)的反应容器中,在用搅拌器搅拌的状态下,加入CUREZOL C11Z(四国化成工业公司制,5.14g,24.3mmol),加热至60℃使之溶解。用约5分钟向所得到的溶解液中少量逐步加入了DENACOL EX-731(Nagase Chemtex公司制,5.00g,23.1mmol)。全部溶解后,加热至70℃,在该温度下搅拌了23小时。冷却至常温后,加水(约20mL)在15℃的温度下搅拌,使结晶析出。将所得到的结晶抽滤,用水清洗后干燥,得到粗结晶5.70g。
将1.8mL的1N盐酸加入到3.00g的粗结晶中,在乳钵中研碎,向所得到的粉体中加水,使其悬浊。对所得到的悬浊液进行吸滤,使固体溶解在氯仿(约50mL)中并移至分液漏斗,将所得到的溶液依次用水→饱和小苏打水→食盐水清洗。用硫酸镁将氯仿层脱水后,用液相分离滤纸进行过滤,用旋转蒸发器将有机层浓缩。将乙酸乙酯和己烷加入到所得到的白色固体中,使其悬浊后,对悬浊液进行吸滤,将所得到的结晶减压干燥,得到化合物4(1.97g)。生成物的物性测定值如下所示。
1H NMR(400MHz 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-异吲哚-1,3(2H)-二酮
化合物5(CAS登记号:858512-76-2)使用了市售品(购自FCH Group公司)。
(化合物6)2-[2-(1H-咪唑-1-基)乙基]-1H-异吲哚-1,3(2H)-二酮
化合物6(CAS登记号:72459-53-1)使用了市售品(购自Enamine公司)。
(化合物7)1-(2-甲基-1H-咪唑-1-基)-3-苯氧基丙烷-2-醇的合成
将2-甲基-1H-咪唑(四国化成工业公司制,21.8g,266mmol)溶于甲苯(78.7mL)和甲醇(17.7mL)的混合溶剂中,升温至80℃,用1小时滴加DENACOL EX-141(Nagase Chemtex公司制,22.0g,147mmol)的甲苯(38.1mL)溶液,然后在该温度下搅拌1小时。将所得到的溶液冷却至室温,在减压下蒸馏除去溶剂,得到黄色固体的1-(2-甲基-1H-咪唑-1-基)-3-苯氧基丙烷-2-醇(47.85g)。生成物的鉴定采用1H NMR进行,确认得到了目标物。
(化合物8)2MZ-H
化合物8采用了市售品(购自四国化成工业公司)。
==化合物的评价方法==
<熔点的测定>
使用差示扫描量热测定装置(DSC 204F1Phoenix(注册商标))(NETZSCH公司制)对熔点进行了测定。首先,在铝盘中量取合成的化合物5mg,用铝制盖密封之后,用针在该盖的中心开孔,准备了测定样品。接着,在氮气气氛下(100mL/分钟),在25~250℃的范围内,以速度10℃/分钟的条件一边升温,一边对该测定样品进行热流(mW/mg)测定。使用分析软件(NETZSCH Proteus-Thermal Analysis version 8.0.2)计算出与熔点相当的图表上能够得到峰值的温度。
将化合物的评价结果表示在表1中。
[表1]
ND:未检测到
==树脂组合物的制备方法==
<实施例1~4、6、比较例1、2:环氧-硫醇固化系>
将作为固化催化剂的化合物1~4、7、8投入到作为环氧树脂的EXA835LV(DIC公司制)中混合。之后,在乳钵中研磨至没有凝集,使用行星型搅拌消泡装置,在真空下进行搅拌和消泡。向其中投入EXA835LV或EXA835LV与CDMDG(昭和电工公司制)的混合物进行混合。然后,使用行星型搅拌消泡装置,在真空下进行搅拌和消泡。再投入作为硫醇树脂的PEMP(SC有机化学公司制)并进行混合。然后使用行星型搅拌消泡装置,在真空下进行搅拌和消泡,得到了树脂组合物。
<实施例5:环氧-硫醇固化系>
向用三根辊磨机将EXA835LV和TS720(Cabot Specialty Chemicals公司制)分散后的混合物中投入作为固化催化剂的化合物1,进行混合。之后,在乳钵中研磨至没有凝集,使用行星型搅拌消泡装置,在真空下进行搅拌和消泡。向其中投入作为硫醇树脂的C3TSG(四国化成工业公司制)进行混合。之后,使用行星搅拌消泡装置,在真空下进行搅拌和消泡,得到了树脂组合物。
<实施例7、11、12:环氧树脂均聚固化系>
将作为固化催化剂的化合物1、化合物5和化合物6投入到EXA835LV中进行混合。之后,在乳钵中研磨至没有凝集,使用行星型搅拌消泡装置,在真空下进行搅拌和消泡,得到了树脂组合物。
<实施例8:环氧-酸酐固化系>
将作为固化催化剂的化合物1投入到作为环氧树脂的EXA835LV中进行混合。之后,在乳钵中研磨至没有凝集,使用行星型搅拌消泡装置,在真空下进行搅拌和消泡。向其中投入YDF8170(新日铁住金化学公司制)进行混合。然后,使用行星型搅拌消泡装置,在真空下进行搅拌和消泡。再向其中投入作为酸酐树脂的YH306(三菱化学公司制)并进行混合。然后,使用行星型搅拌消泡装置,在真空下进行搅拌和消泡,得到了树脂组合物。
<实施例9:环氧-苯酚固化系>
将作为固化催化剂的化合物1投入到EXA835LV中进行混合。之后,在乳钵中研磨至没有凝集,使用行星型搅拌消泡装置,在真空下进行搅拌和消泡。向其中投入EXA835LV进行混合。然后,使用行星型搅拌消泡装置,在真空下进行搅拌和消泡。再向其中加入作为酚醛树脂的MEH8005(明和化成公司制)进行混合。然后,使用行星型搅拌消泡装置,在真空下进行搅拌和消泡,得到了树脂组合物。
<实施例10:丙烯酰-硫醇固化系>
向用三根辊磨机将作为丙烯酸树脂的M7100(东亚合成公司制)、作为光自由基引发剂的OMNIRAD184(IGM resins B.V.公司制)、作为阻聚剂的Q-1301(富士胶片和光纯药公司制)、作为触变剂的TS720分散,向所得到的混合物中投入作为固化催化剂的化合物1,再用三根辊磨机进行分散。向其中投入PEMP进行混合后,使用行星型搅拌消泡装置,在真空下进行搅拌和消泡,得到了树脂组合物。
==树脂组合物的评价方法==
<适用期的测定>
使用E型粘度计(TVE-25H:东机产业公司制,转子名称:3°×R9.7),在50rpm、25℃的条件下,在预定的适当范围(H、R或U)内测定树脂组合物的初始粘度。接着,将贮存在密闭容器中的树脂组合物在25℃、湿度50%的环境下放置4小时,将4小时内未固化的制品的适用期标记为○、发生了固化的适用期标记为×。此后,每4小时使用E型粘度计(TVE-25H:东机产业公司制,转子名称:3°×R9.7),在50rpm、25℃的条件下,在预定的适当范围(H、R或U)内测定该树脂组合物的粘度。然后,计算(各时间的放置后的粘度)/(初始粘度),作为各时间的放置后的增粘倍率。
<凝胶时间的测定>
使用凝胶化试验机(GT-D-15A:Eucaly Giken公司制)对凝胶化之前的时间(称为凝胶时间)进行测定。将加热板设定为100℃、120℃或150℃,用试验棒将树脂组合物转印至加热板上。用试验棒接触树脂组合物,并将出现拉丝状态为止的时间设为凝胶时间。
==结果==
将以上的树脂组合物的各构成成分的用量和评价结果汇总于表2~3中。
[表2]
UM:未能测定
(斜线表示未测定)
[表3]
UM:未能测定
(斜线表示未测定)
实施例所使用的固化催化剂的熔点高于比较例1的固化催化剂的熔点。比较例2虽然熔点高,但分子量小,因此易溶于环氧树脂等而缺乏稳定性。
根据树脂组合物的适用期的比较可知,在比较例中,4小时内已经固化,相对于此,在实施例中,增粘率达到2倍时,均在8小时以上。
实施例中的树脂组合物在10分钟以内凝胶化,具有足够的反应性和固化性。
因此,本发明的固化催化剂因具有邻苯二甲酰亚胺骨架而结晶性高,比以往的加成了环氧树脂和咪唑衍生物的加成物的熔点还高,且通过本发明的固化催化剂,能够得到稳定的、不易发生在非预期的温度内固化催化剂向树脂中溶解的树脂组合物。
Claims (12)
1.一种固化催化剂,其特征在于:
含有下述结构式(I)的化合物,
式中,R1为选自氢、苯基和C1~C17的烷基的基团,
R2、R3、R5分别独立地为选自氢和C1~C6的烷基的基团,R4为选自氢、OH和OAc的基团,
n和m为整数,n和m之和为1以上12以下。
2.如权利要求1所述的固化催化剂,其特征在于:
n和m之和为3以下。
3.一种树脂组合物,其特征在于:
含有权利要求1或2所述的固化催化剂和热固性树脂。
4.如权利要求3所述的树脂组合物,其特征在于:
所述热固性树脂为环氧树脂。
5.如权利要求4所述的树脂组合物,其特征在于:
所述热固性树脂为具有聚合性双键的化合物。
6.如权利要求4或5所述的树脂组合物,其特征在于:
所述树脂组合物还含有所述热固性树脂的固化剂。
7.如权利要求4~6中任一项所述的树脂组合物,其特征在于:所述固化剂为选自含氧化合物、含氮化合物和硫醇化合物中之一。
8.一种密封材料,其特征在于:
含有权利要求3~7中任一项所述的树脂组合物。
9.一种粘接剂,其特征在于:
含有权利要求3~7中任一项所述的树脂组合物。
10.一种权利要求3~7中任一项所述的树脂组合物的固化物。
11.一种下述结构式(I)的化合物,其中,
式中,R1为选自苯基和C1~C17的烷基的基团,
R2、R3、R5分别独立地为选自氢和C1~C6的烷基的基团,R4为选自OH和OAc的基团,
n和m为整数,n和m之和为1以上12以下。
12.如权利要求11所述的化合物,其特征在于:
式中,R1为选自苯基和C1~C10的烷基的基团,
R2、R3、R5为氢,
R4为OH,
n和m为1。
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