CN118369320A - 化合物、固化性树脂组合物及固化物 - Google Patents
化合物、固化性树脂组合物及固化物 Download PDFInfo
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- CN118369320A CN118369320A CN202380014927.8A CN202380014927A CN118369320A CN 118369320 A CN118369320 A CN 118369320A CN 202380014927 A CN202380014927 A CN 202380014927A CN 118369320 A CN118369320 A CN 118369320A
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- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
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- 229920001451 polypropylene glycol Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
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- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
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- 235000007586 terpenes Nutrition 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
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- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229960004319 trichloroacetic acid Drugs 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-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
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
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- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
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- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
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- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
下述式(1)所表示的化合物。式中,R1表示氢原子或甲基,R2~R5分别独立地表示氢原子、碳数1~10的烷基、碳数1~10的烷氧基、碳数1~10的烷酰氧基、碳数1~10的烷氧基羰基、碳数1~10的烷基酰胺基、卤素原子、羟基、硝基或腈基,A1表示碳数1~20的亚烷基,A2表示亚丙基或异亚丙基。
Description
技术领域
本发明涉及化合物及固化性树脂组合物。详细而言,涉及具有环氧基的酰亚胺化合物,此外还涉及含有上述化合物、环氧树脂及固化剂的固化性树脂组合物。
背景技术
环氧树脂作为涂料、粘接剂、各种成形材料等成分在工业上被广泛使用。
在将环氧树脂用于上述用途的情况下,通常与固化剂组合使用,作为该固化剂,已知有酸酐系固化剂、胺系固化剂、酚系固化剂等各种固化剂。
上述固化剂根据用途而分开使用,例如,咪唑系固化剂与加聚型固化剂不同,由于为阴离子聚合型固化剂,因此能够以少量添加进行固化,此外为低挥发性且毒性低这点也有用,因此可以适宜用于电气、电子部件。
然而,在单独使用咪唑系固化剂的情况下,难以取得固化性与储存稳定性的平衡。为了提高储存稳定性,例如在专利文献1中,提出了将咪唑化合物与环氧树脂的反应物用于环氧固化系统,在专利文献2中,提出了包含改性咪唑、改性胺及酚类化合物的环氧树脂用固化剂组合物。
另一方面,即使是使用这些各种改性咪唑的情况下,固化性树脂组合物的储存稳定性也还不能够令人满意。
现有技术文献
专利文献
专利文献1:美国专利第4066625号说明书
专利文献2:日本特开2007-297493号公报
发明内容
发明所要解决的课题
因此,本发明所要解决的课题是提供可得到储存稳定性优异的固化性树脂组合物的材料。
用于解决课题的手段
本发明人们进行了深入研究,结果发现:酰亚胺部位与环氧部位通过硫醚键键合而得到的特定的化合物可提高储存稳定性,达成了本发明。
即,本发明为下述式(1)所表示的化合物。
[化学式1]
式中,R1表示氢原子或甲基,R2、R3、R4及R5(以下也记载为“R2~R5”。)分别独立地表示氢原子、碳数1~10的烷基、碳数1~10的烷氧基、碳数1~10的烷酰氧基、碳数1~10的烷氧基羰基、碳数1~10的烷基酰胺基、碳数1~10的酰基氨基、卤素原子、羟基、硝基或腈基,A1表示碳数1~20的亚烷基,A2表示亚丙基或异亚丙基。
此外,本发明提供一种固化性树脂组合物,其含有作为(A)成分的上述化合物、作为(B)成分的环氧树脂、及作为(C)成分的固化剂。
此外,本发明提供上述固化性树脂组合物的固化物。
发明效果
根据本发明,能够提供固化物的热稳定性优异、并且储存稳定性优异的固化性树脂组合物。本发明的固化性树脂组合物可以作为单组分固化型的固化性树脂组合物适宜地使用。
附图说明
图1是表示实施例1中制造的化合物的1H-NMR测定结果的图。
具体实施方式
以下,对本发明的化合物进行说明。
本发明的化合物为下述式(1)所表示的化合物。
[化学式2]
上述式(1)中,R1表示氢原子或甲基,R2~R5分别独立地表示氢原子、碳数1~10的烷基、碳数1~10的烷氧基、碳数1~10的烷酰氧基、碳数1~10的烷氧基羰基、碳数1~10的烷基酰胺基、碳数1~10的酰基氨基、卤素原子、羟基、硝基或腈基,A1表示碳数1~20的亚烷基,A2表示亚丙基或异亚丙基。
作为上述式(1)中的R2~R5所表示的碳数1~10的烷基,例如可列举出甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、戊基、异戊基、叔戊基、己基、庚基、辛基、2-乙基己基、壬基、异壬基、癸基及异癸基等。
作为上述式(1)中的R2~R5所表示的碳数1~10的烷氧基,例如可列举出甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、戊氧基、己氧基、庚氧基、辛氧基、壬氧基及癸氧基等。
作为上述式(1)中的R2~R5所表示的碳数1~10的烷酰氧基,例如可列举出甲酰氧基、乙酰氧基、丙酰氧基、丁酰氧基、庚酰氧基、辛酰氧基、壬酰氧基、癸酰氧基等。
作为上述式(1)中的R2~R5所表示的碳数1~10的烷氧基羰基,例如可列举出甲氧基羰基、乙氧基羰基、丙氧基羰基、丁氧基羰基、戊氧基羰基、己氧基羰基、庚氧基羰基、辛氧基羰基、壬氧基羧基、癸氧基羰基等。
作为上述式(1)中的R2~R5所表示的碳数1~10的烷基酰胺基,例如可列举出甲基酰胺基、乙基酰胺基、丙基酰胺基、丁基酰胺基、戊基酰胺基、己基酰胺基、庚基酰胺基、辛基酰胺基、壬基酰胺基、癸基酰胺基等。
作为上述式(1)中的R2~R5所表示的碳数1~10的酰基氨基,例如可列举出甲基酰基氨基、乙基酰基氨基、正丙基酰基氨基、异丙基酰基氨基、叔丁基酰基氨基、N,N-二甲基酰基氨基、N,N-二乙基酰基氨基、N,N-二正丙基酰基氨基、N,N-二异丙基酰基氨基、N,N-二叔丁基酰基氨基。
作为上述式(1)中的R2~R5所表示的卤素原子,例如可列举出氟、氯、溴及碘等。
作为上述式(1)中的A2所表示的碳数1~20的亚烷基,例如可列举出亚甲基、亚乙基、亚丙基、异亚丙基、亚丁基、亚戊基、亚己基、亚庚基、亚辛基、亚壬基、亚癸基、亚十一烷基、亚十二烷基、亚十三烷基、亚十四烷基、亚十五烷基、亚十六烷基、亚十七烷基、亚十八烷基、亚十九烷基、亚二十烷基等。
上述式(1)所表示的化合物中,从能够容易地制造的方面出发,优选R2~R5分别独立地为氢原子、碳数1~4的烷基、卤素原子、羟基或硝基的化合物,特别优选R3或R4为氢原子、碳数1~4的烷基、卤素原子、羟基或硝基的化合物。尤其特别优选R2、R4及R5为氢原子、R3为氢原子、碳数1~4的烷基、卤素原子、羟基或硝基的化合物。
此外,优选A1为碳数1~4的亚烷基的化合物,更优选为碳数1~3的亚烷基的化合物,特别优选为碳数1~2的亚烷基的化合物。
进而,R1为氢原子从原料的获得容易的方面考虑优选。
上述式(1)所表示的化合物中优选的化合物为下述式(1A)所表示的化合物和/或(1B)所表示的化合物,也可以为它们的混合物。在为混合物的情况下,下述式(1A)所表示的化合物和/或(1B)所表示的化合物的质量比以(1A):(1B)计也可以为1:0.01~100。
[化学式3]
上述式(1A)中,R1a表示氢原子或甲基,R6分别独立地表示氢原子、碳数1~4的烷基、卤素原子、羟基或硝基。
[化学式4]
上述式(1B)中,R1b表示氢原子或甲基,R7分别独立地表示氢原子、碳数1~4的烷基、卤素原子、羟基或硝基。
尤其是在上述式(1A)所表示的化合物及上述式(1B)所表示的化合物中,作为对于R1a及R1b优选的基团,可列举出作为上述R1在上文叙述的基团。尤其是作为R3、R6及R7,优选氢原子、甲基、卤素原子、硝基。作为上述式(1)所表示的化合物中优选的化合物,在使用式(1A)所表示的化合物及上述式(1B)所表示的化合物的情况下,式(1A)的R6及式(1B)的R7可以相同,也可以不同。此外在上述的情况下,式(1A)的R1a及式(1B)的R1b可以相同,也可以不同。
以下,以下示出特别优选的化合物。
[化学式5]
[化学式6]
[化学式7]
[化学式8]
[化学式9]
[化学式10]
[化学式11]
[化学式12]
[化学式13]
[化学式14]
[化学式15]
[化学式16]
[化学式17]
[化学式18]
本发明的式(1)所表示的化合物的制造方法没有特别限定,例如可以按照下述方案来制造。
这里,硫醇化合物(a)与烯丙基缩水甘油醚和/或烯丙基β-甲基缩水甘油醚(以下,有时也一并记载为“烯丙基缩水甘油醚类”)(b)的反应通过在硫醇化合物(a)与烯丙基缩水甘油醚类(b)的不饱和键之间引起的硫醇烯反应而进行。
[化学式19]
上述式中的R1~R5、A1及A2与上述式(1)中的各符号相同。
上述反应中使用的硫醇化合物(a)是公知化合物,其制造方法没有限制,但例如是通过使可具有取代基的邻苯二甲酸酐与氨基烷烃硫醇在溶剂中反应而容易地获得的硫醇化合物。作为氨基烷烃硫醇,可列举出氨基甲烷硫醇、2-氨基乙烷硫醇、3-氨基-1-丙烷硫醇、4-氨基-1-丁烷硫醇、5-氨基-1-戊烷硫醇、6-氨基-1-己烷硫醇等。
作为上述可具有取代基的邻苯二甲酸酐与氨基烷烃硫醇的反应中使用的溶剂,没有特别限制,但例如可列举出戊烷、己烷、庚烷、环己烷等饱和烃类;苯、甲苯、二甲苯、乙基苯等芳香族烃类;二氯甲烷、氯仿、四氯化碳、二氯乙烷、氯苯、二氯苯等卤代烃类;二乙基醚、二异丙基醚、1,2-二甲氧基乙烷、双(2-甲氧基乙基)醚、1,2-双(2-甲氧基乙氧基)乙烷、双〔2-(2-甲氧基乙氧基)乙基〕醚、四氢呋喃、1,3-二噁烷、1,4-二噁烷、茴香醚等醚类;苯酚、邻氯苯酚、间氯苯酚、对氯苯酚、邻甲酚、间甲酚、对甲酚、2,3-二甲苯酚、2,4-二甲苯酚、2,5-二甲苯酚、2,6-二甲苯酚、3,4-二甲苯酚、3,5-二甲苯酚等酚类;N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N,N-二乙基乙酰胺、N,N-二甲基甲氧基乙酰胺、六甲基磷酰胺等酰胺类;N-甲基-2-吡咯烷酮、N-甲基己内酰胺等内酰胺类;二甲基亚砜、二苯基亚砜、二甲基砜、二苯基砜、环丁砜等含硫溶剂类、1,3-二甲基-2-咪唑烷酮等。这些有机溶剂可以单独使用,也可以将2种以上混合使用。
有机溶剂的使用量没有特别限制,相对于可具有取代基的邻苯二甲酸酐与氨基烷烃硫醇的合计1质量份为0.1~10000质量份,优选为1~100质量份。反应有机溶剂优选将原料溶解而制成溶液,但也可以以浆料状态进行反应。
上述可具有取代基的邻苯二甲酸酐与氨基烷烃硫醇的反应也可以在通常的酰亚胺化中使用的有机碱催化剂或酸催化剂的存在下进行。
作为上述有机碱催化剂,例如可列举出三乙基胺、三丁基胺、三戊基胺、N,N-二甲基苯胺、N,N-二乙基苯胺、吡啶、α-甲基吡啶、β-甲基吡啶、γ-甲基吡啶、2,4-二甲基吡啶、2,6-二甲基吡啶、喹啉及异喹啉等,但优选吡啶及γ-甲基吡啶。这些有机碱催化剂可以单独使用,也可以将2种以上组合使用。
作为上述酸催化剂,例如可列举出盐酸、氢溴酸、氢碘酸、硫酸、无水硫酸、硝酸、磷酸、亚磷酸、磷钨酸、磷钼酸等无机酸类;甲磺酸、乙磺酸、三氟甲磺酸、苯磺酸、对甲苯磺酸等磺酸类;乙酸、草酸等羧酸类;氯乙酸、二氯乙酸、三氯乙酸、氟乙酸、二氟乙酸、三氟乙酸等卤代羧酸类;二氧化硅、氧化铝、活性白土等固体酸类;阳离子型离子交换树脂等。特别优选硫酸、磷酸及对甲苯磺酸。这些酸催化剂可以单独使用,也可以将2种以上组合使用。此外这些酸催化剂也可以为与二胺化合物的盐。
上述催化剂的使用量只要是反应速度实质上提高则没有特别限制,相对于可具有取代基的邻苯二甲酸酐及氨基烷烃硫醇的合计1摩尔为0.001~10摩尔,优选为0.005~5摩尔,进一步优选为0.01~1摩尔。
上述可具有取代基的邻苯二甲酸酐与氨基烷烃硫醇的反应时间根据所使用的原料的种类、溶剂的种类、催化剂的种类、及反应温度等而不同,作为标准,为1~24小时,通常为数小时。在直接进行热酰亚胺化时,作为标准,将反应进行至馏出的水大致达到理论量为止。
上述酸酐与氨基烷烃硫醇的反应中的压力没有特别限制,但通常设定为大气压即可。反应气氛没有特别限制,但通常为空气、氮、氦、氖或氩气氛,优选为不活泼气体即氮及氩气氛。
在上述反应结束后,将式(a)所表示的硫醇化合物离析的方法没有特别限定,在目标物从反应溶剂中析出的情况下,只要通过过滤或离心分离来离析即可。另一方面,在目标物溶解于溶剂中的情况下,只要在减压下将溶剂蒸馏除去、或在反应混合物中添加适当的不良溶剂、或将反应混合物排出到不良溶剂中等而析出,通过过滤或离心分离进行离析即可。
在需要将所离析的式(a)所表示的硫醇化合物进一步精制的情况下,只要采用作为常规方法已知的方法进行精制即可,作为其方法,可列举出蒸馏精制法、再结晶法、柱色谱法、污泥处理及活性炭处理等。
此外,烯丙基缩水甘油醚和/或烯丙基β-甲基缩水甘油醚(b)可以通过使烯丙基醇与环氧氯丙烷和/或β-甲基环氧氯丙烷在催化剂存在下根据需要在溶剂中在20~120℃下进行几小时~十几小时反应来获得。
作为上述反应中使用的催化剂,例如可列举出碱性化合物、有机磷系化合物、叔胺、及路易斯酸等。作为碱性化合物,例如可列举出氢氧化锂、氢氧化钠、氢氧化钾、氢氧化钙、氢氧化镁等碱金属或碱土类金属的氢氧化物。作为有机磷系化合物,例如可列举出三环己基膦、三丁基膦、三辛基膦、环己基二苯基膦、二环己基苯基膦、丁基二苯基膦、二丁基苯基膦、辛基二苯基膦、二辛基苯基膦、三苯基膦等。作为叔胺,可列举出三甲基胺、三乙基胺、三丙基胺、三丁基胺、二氮杂二环十一碳烯、二氮杂二环壬烯、1-甲基咪唑等。作为路易斯酸,例如可列举出三氟化硼、氯化铝、甲基二氯化铝、二甲基氯化铝、三甲基铝、氯化镁、溴化镁、四氯化钛、双三氟甲磺酸二氯钛、二环戊二烯钛双三氟甲磺酸盐、双氟磺酸二氯钛、四氯化锡、双三氟甲磺酸锡(II)等。上述催化剂可以单独使用1种,也可以将2种以上组合使用。
作为上述反应中使用的溶剂,例如可列举出甲基溶纤剂、乙基溶纤剂、异丙基溶纤剂、丁基溶纤剂、丙二醇单甲基醚、二乙二醇单甲基醚、三乙二醇单甲基醚、聚乙二醇单甲基醚、乙二醇二甲基醚、二乙二醇二甲基醚、三乙二醇二甲基醚及聚乙二醇二甲基醚等二醇醚溶剂;乙酸乙酯、乙酸丁酯、乙酸戊酯、乳酸乙酯及苯甲酸甲酯等酯系溶剂;直链己烷、直链庚烷及直链辛烷等脂肪族烃系溶剂;环己烷及乙基环己烷等脂环式烃系溶剂;丙酮、甲乙酮及甲基异丁基酮等酮系溶剂;苯、甲苯及二甲苯等芳香族烃溶剂;以及石油系溶剂等。上述溶剂可以单独使用1种,也可以将2种以上组合使用。
上述硫醇化合物(a)与烯丙基缩水甘油醚类(b)的反应可以通过在溶剂中使用催化剂在15~100℃下反应几小时~几天来制造。
需要说明的是,在上述反应中,由于烯丙基的α位与β位处的反应的控制困难,因此以混合物得到A2为直链亚丙基的化合物与为异亚丙基的化合物,但它们可以不进行离析地使用。
作为上述反应中可以使用的催化剂,可以使用公知的热自由基引发剂,例如可列举出2,2’-偶氮双异丁腈、2,2’-偶氮双(甲基异丁酸酯)、2,2’-偶氮双-2,4-二甲基戊腈、1,1’-偶氮双(1-乙酰氧基-1-苯基乙烷)等偶氮系化合物;过氧化苯甲酰、二叔丁基过氧化苯甲酰、过氧化特戊酸叔丁酯及二(4-叔丁基环己基)过氧化二碳酸酯等过氧化物;过硫酸铵、过硫酸钠及过硫酸钾等过硫酸盐等。
催化剂的使用量只要是反应速度实质上提高则没有特别限制,相对于硫醇化合物(a)及烯丙基缩水甘油醚类(b)的合计1摩尔为0.001~10摩尔,优选为0.005~5摩尔,进一步优选为0.01~1摩尔。
在上述硫醇化合物(a)与上述烯丙基缩水甘油醚类(b)的反应中使用溶剂是任选的,作为所使用的溶剂,没有特别限制,例如可列举出戊烷、己烷、庚烷、环己烷等饱和烃类;苯、甲苯、二甲苯、乙基苯等芳香族烃类;二氯甲烷、氯仿、四氯化碳、二氯乙烷、氯苯、二氯苯等卤代烃类;二乙基醚、二异丙基醚、1,2-二甲氧基乙烷、双(2-甲氧基乙基)醚、1,2-双(2-甲氧基乙氧基)乙烷、双〔2-(2-甲氧基乙氧基)乙基〕醚、四氢呋喃、1,3-二噁烷、1,4-二噁烷、茴香醚等醚类;苯酚、邻氯苯酚、间氯苯酚、对氯苯酚、邻甲酚、间甲酚、对甲酚、2,3-二甲苯酚、2,4-二甲苯酚、2,5-二甲苯酚、2,6-二甲苯酚、3,4-二甲苯酚、3,5-二甲苯酚等酚类;N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N,N-二乙基乙酰胺、N,N-二甲基甲氧基乙酰胺、六甲基磷酰胺等酰胺类;N-甲基-2-吡咯烷酮、N-甲基己内酰胺等内酰胺类;二甲基亚砜、二苯基亚砜、二甲基砜、二苯基砜、环丁砜等含硫溶剂类、1,3-二甲基-2-咪唑烷酮等。这些有机溶剂可以单独使用,也可以将2种以上混合使用。
上述溶剂的使用量没有特别限制,相对于硫醇化合物(a)与烯丙基缩水甘油醚类(b)的合计1质量份为0.1~10000质量份,优选为1~100质量份。溶剂优选将原料溶解而制成溶液,但也可以以浆料状态进行反应。
反应时间根据所使用的原料的种类、溶剂的种类、催化剂的种类、及反应温度等而不同,作为标准,为1~24小时,通常为几小时。
上述反应中的反应压力没有特别限制,通常设定为大气压即可。反应气氛没有特别限制,通常为空气、氮、氦、氖或氩气氛,优选为不活泼气体即氮及氩气氛。
在上述反应结束后,将式(1)所表示的化合物离析的方法没有特别限定,在目标物从溶剂析出的情况下,只要通过过滤或离心分离进行离析即可。另一方面,在目标物溶解于溶剂中的情况下,只要在减压下将溶剂蒸馏除去、或在反应混合物中添加适当的不良溶剂、或将反应混合物排出到不良溶剂中等而析出,通过过滤或离心分离进行离析即可。
在需要将所离析的式(1)所表示的化合物进一步精制的情况下,只要采用作为常规方法已知的方法进行精制即可,作为其方法,可列举出蒸馏精制法、再结晶法、柱色谱法、污泥处理及活性炭处理等。
接下来,对本发明的固化性树脂组合物进行说明。
本发明的固化性树脂组合物含有作为(A)成分的上述式(1)所表示的化合物、作为(B)成分的环氧树脂、及作为(C)成分的固化剂。
本发明中使用的(B)成分即环氧树脂只要是在分子中具有至少2个环氧基即可,可以对分子结构、分子量等没有特别限制地使用。
作为上述环氧树脂,可列举出氢醌、间苯二酚、焦儿茶酚和间苯三酚等单核多元酚化合物的聚缩水甘油醚化物;二羟基萘、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-羟基枯基苯)、1,4-双(4-羟基枯基苯)、1,1,3-三(4-羟基苯基)丁烷、1,1,2,2-四(4-羟基苯基)乙烷、硫代双酚、磺基双酚、氧代双酚、苯酚酚醛清漆、邻甲酚酚醛清漆、乙基苯酚酚醛清漆、丁基苯酚酚醛清漆、辛基苯酚酚醛清漆、间苯二酚酚醛清漆和萜烯酚等多核多元酚化合物的聚缩水甘油醚化物;乙二醇、丙二醇、丁二醇、己二醇、聚乙二醇、聚丙二醇、硫甘醇、二环戊二烯二甲醇、2,2-双(4-羟基环己基)丙烷(氢化双酚A)、甘油、三羟甲基丙烷、季戊四醇、山梨糖醇和双酚A-环氧烷烃加成物等多元醇化合物的聚缩水甘油醚化物;马来酸、富马酸、衣康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、偏苯三酸、均苯三甲酸、均苯四甲酸、四氢邻苯二甲酸和桥亚甲基四氢邻苯二甲酸等脂肪族、芳香族或脂环族多元酸的缩水甘油酯化物及甲基丙烯酸缩水甘油酯的均聚物或共聚物;N,N-二缩水甘油基苯胺、双(4-(N-甲基-N-缩水甘油基氨基)苯基)甲烷、二缩水甘油基邻甲苯胺、N,N-双(2,3-环氧丙基)-4-(2,3-环氧丙氧基)-2-甲基苯胺、N,N-双(2,3-环氧丙基)-4-(2,3-环氧丙氧基)苯胺和N,N,N’,N’-四(2,3-环氧丙基)-4,4-二氨基二苯基甲烷等具有缩水甘油基氨基的环氧化合物;乙烯基环己烯二环氧化物、环戊二烯二环氧化物、3,4-环氧环己基甲基-3,4-环氧环己烷羧酸酯、3,4-环氧-6-甲基环己基甲基-6-甲基环己烷羧酸酯和双(3,4-环氧-6-甲基环己基甲基)己二酸酯等环状烯烃化合物的环氧化物;环氧化聚丁二烯和环氧化苯乙烯-丁二烯共聚物等环氧化共轭二烯聚合物;异氰脲酸三缩水甘油酯等杂环化合物。此外,这些环氧树脂也可以以通过末端异氰酸酯的预聚物而内部交联的形式、此外以多价的活性氢化合物(多元酚、多胺、含羰基化合物、多磷酸酯等)高分子量化的形式使用。环氧树脂可以单独使用,也可以将2种以上并用。
作为本发明中使用的(C)成分即固化剂,例如可列举出酸酐系固化剂、酚系固化剂、胺系固化剂、聚硫醇系固化剂及咪唑系固化剂等。
作为上述酸酐系固化剂,例如可列举出降冰片烯二酸酐、邻苯二甲酸酐、马来酸酐、甲基降冰片烯二酸酐、琥珀酸酐、四氢邻苯二甲酸酐、六氢邻苯二甲酸酐、甲基四氢邻苯二甲酸酐、甲基六氢邻苯二甲酸酐、三烷基四氢邻苯二甲酸酐-马来酸酐加成物、二苯甲酮四羧酸酐、偏苯三酸酐、均苯四甲酸酐及氢化甲基纳迪克酸酐等。
作为上述酚系固化剂,例如可列举出苯酚酚醛清漆树脂、甲酚酚醛清漆树脂、芳香族烃甲醛树脂改性酚醛树脂、二环戊二烯苯酚加成型树脂、苯酚芳烷基树脂(Xylocresins)、萘酚芳烷基树脂、三苯酚基甲烷树脂、四苯酚基乙烷树脂、萘酚酚醛清漆树脂、萘酚-苯酚共缩合酚醛清漆树脂、萘酚-甲酚共缩合酚醛清漆树脂、联苯改性酚醛树脂(苯酚核通过双亚甲基连接而成的多元酚化合物)、联苯改性萘酚树脂(苯酚核通过双亚甲基连接而成的多元萘酚化合物)、氨基三嗪改性酚醛树脂(在分子结构中具有苯酚骨架、三嗪环及伯氨基的化合物)及含烷氧基的芳香环改性酚醛清漆树脂(苯酚核及含烷氧基的芳香环通过甲醛连接而成的多元酚化合物)等多元酚化合物。
作为上述胺系固化剂,例如可列举出乙二胺、1,2-二氨基丙烷、1,3-二氨基丙烷、1,3-二氨基丁烷、1,4-二氨基丁烷、六亚甲基二胺及间苯二甲胺等亚烷基二胺类;二亚乙基三胺、三亚乙基三胺和四亚乙基五胺等多烷基多胺类;1,4-二氨基环己烷、1,3-二氨基环己烷、1,3-二氨基甲基环己烷、1,2-二氨基环己烷、1,4-二氨基-3,6-二乙基环己烷、4,4’-二氨基二环己基甲烷、1,3-双(氨基甲基)环己烷、1,4-双(氨基甲基)环己烷、4,4’-二氨基二环己基丙烷、双(4-氨基环己基)砜、4,4’-二氨基二环己基醚、2,2’-二甲基-4,4’-二氨基二环己基甲烷、异佛尔酮二胺和降冰片烯二胺等脂环式多胺类;二氨基二苯基甲烷、二氨基二苯基砜、二乙基甲苯二胺、1-甲基-3,5-二乙基-2,4-二氨基苯、1-甲基-3,5-二乙基-2,6-二氨基苯、1,3,5-三乙基-2,6-二氨基苯、3,3’-二乙基-4,4’-二氨基二苯基甲烷和3,5,3’,5’-四甲基-4,4’-二氨基二苯基甲烷等芳香族多胺类;N,N-二甲基氨基乙基胺、N,N-二乙基氨基乙基胺、N,N-二异丙基氨基乙基胺、N,N-二烯丙基氨基乙基胺、N,N-苄基甲基氨基乙基胺、N,N-二苄基氨基乙基胺、N,N-环己基甲基氨基乙基胺、N,N-二环己基氨基乙基胺、N-(2-氨基乙基)吡咯烷、N-(2-氨基乙基)哌啶、N-(2-氨基乙基)吗啉、N-(2-氨基乙基)哌嗪、N-(2-氨基乙基)-N’-甲基哌嗪、N,N-二甲基氨基丙基胺、N,N-二乙基氨基丙基胺、N,N-二异丙基氨基丙基胺、N,N-二烯丙基氨基丙基胺、N,N-苄基甲基氨基丙基胺、N,N-二苄基氨基丙基胺、N,N-环己基甲基氨基丙基胺、N,N-二环己基氨基丙基胺、N-(3-氨基丙基)吡咯烷、N-(3-氨基丙基)哌啶、N-(3-氨基丙基)吗啉、N-(3-氨基丙基)哌嗪、N-(3-氨基丙基)-N’-甲基哌啶、4-(N,N-二甲基氨基)苄基胺、4-(N,N-二乙基氨基)苄基胺、4-(N,N-二异丙基氨基)苄基胺、N,N-二甲基异佛尔酮二胺、N,N-二甲基双氨基环己烷、N,N,N’-三甲基乙二胺、N’-乙基-N,N-二甲基乙二胺、N,N,N’-三乙基乙二胺、N’-乙基-N,N-二甲基丙二胺、N’-乙基-N,N-二苄基氨基丙基胺;N,N-(双氨基丙基)-N-甲基胺、N,N-双氨基丙基乙基胺、N,N-双氨基丙基丙基胺、N,N-双氨基丙基丁基胺、N,N-双氨基丙基戊基胺、N,N-双氨基丙基己基胺、N,N-双氨基丙基-2-乙基己基胺、N,N-双氨基丙基环己基胺、N,N-双氨基丙基苄基胺、N,N-双氨基丙基烯丙基胺、双〔3-(N,N-二甲基氨基丙基)〕胺、双〔3-(N,N-二乙基氨基丙基)〕胺、双〔3-(N,N-二异丙基氨基丙基)〕胺、双〔3-(N,N-二丁基氨基丙基)〕胺;草酸二酰肼、丙二酸二酰肼、琥珀酸二酰肼、戊二酸二酰肼、己二酸二酰肼、辛二酸二酰肼、壬二酸二酰肼、癸二酸二酰肼和邻苯二甲酸二酰肼等二元酸二酰肼;双氰胺、苯并胍胺和乙酰胍胺等胍化合物;三聚氰胺等。
此外,也可以使用将上述胺类改性而得到的改性胺系固化剂。作为改性方法,可列举出与羧酸的脱水缩合、与环氧树脂的加成反应、与异氰酸酯的加成反应、麦克尔加成反应、曼尼希反应、与尿素的缩合反应、及与酮的缩合反应等。
作为上述胺类的改性中可以使用的羧酸,例如可列举出马来酸、富马酸、衣康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、偏苯三酸、均苯三甲酸、均苯四甲酸、四氢邻苯二甲酸、六氢邻苯二甲酸及桥亚甲基四氢邻苯二甲酸等脂肪族、芳香族或脂环族多元酸等。
作为上述胺类的改性中可以使用的环氧化合物,例如可列举出作为上述(B)成分即环氧树脂所例示的环氧化合物。
作为上述胺类的改性中可以使用的异氰酸酯化合物,例如可列举出2,4-甲苯二异氰酸酯、2,6-甲苯二异氰酸酯、二苯基甲烷-4,4’-二异氰酸酯、苯二异氰酸酯、苯二甲基二异氰酸酯、四甲基苯二甲基二异氰酸酯、1,5-萘二异氰酸酯、1,5-四氢萘二异氰酸酯、3,3’-二甲基二苯基-4,4’-二异氰酸酯及二茴香胺二异氰酸酯等芳香族二异氰酸酯;异佛尔酮二异氰酸酯、二环己基甲烷-4,4’-二异氰酸酯、反式-1,4-环己基二异氰酸酯及降冰片烯二异氰酸酯等脂环式二异氰酸酯;四亚甲基二异氰酸酯、1,6-六亚甲基二异氰酸酯、2,2,4和/或(2,4,4)-三甲基六亚甲基二异氰酸酯及赖氨酸二异氰酸酯等脂肪族二异氰酸酯;上述例示的二异氰酸酯的异氰脲酸酯三聚物、缩二脲三聚物及三羟甲基丙烷加成物等;三苯基甲烷三异氰酸酯、1-甲基苯-2,4,6-三异氰酸酯及二甲基三苯基甲烷四异氰酸酯等。进而,这些异氰酸酯化合物也可以以碳二亚胺改性、异氰脲酸酯改性、缩二脲改性等改性物的形式使用,也可以以通过各种的封端剂而封端的封端异氰酸酯的形式使用。
作为上述聚硫醇系固化剂,例如可列举出季戊四醇四(3-巯基丙酸酯)、季戊四醇四(巯基乙酸酯)、二季戊四醇六(3-巯基丙酸酯)、二季戊四醇六(3-巯基丁酸酯)、1,3,4,6-四(2-巯基乙基)-1,3,4,6-四氮杂八氢戊烯-2,5-二酮、1,3,5-三(3-巯基丙基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮、4-巯基甲基-1,8-二巯基-3,6-二硫杂辛烷、4,8-、4,7-或5,7-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷和1,3,4,6-四(2-巯基乙基)甘脲等。
作为上述咪唑系固化剂,例如可列举出2-甲基咪唑、2-乙基-4-甲基咪唑、2-异丙基咪唑、2-十一烷基咪唑、2-十七烷基咪唑、2-苯基咪唑、2-苯基-4-甲基咪唑、2-氨基丙基咪唑、1-苯基甲基-2-咪唑、1-苯基甲基-2-乙基-4-甲基咪唑、1-苯基甲基-2-苯基咪唑、1-丁氧基羰基乙基-2-甲基咪唑、1-丁氧基羰基乙基-2-乙基-4-甲基咪唑、1-丁氧基羰基乙基-2-苯基咪唑、1-(2-乙基己基)羰基乙基-2-甲基咪唑、1-(2-乙基己基)羰基乙基-2-乙基-4-甲基咪唑、1-(2-乙基己基)羰基乙基-2-苯基咪唑、1-辛氧基羰基乙基-2-甲基咪唑、1-辛氧基羰基乙基-2-乙基-4-甲基咪唑、1-辛氧基羰基乙基-2-苯基咪唑、己二醇·双(2-甲基咪唑基乙烷酸)酯、己二醇·双(2-乙基-4-甲基咪唑基乙烷酸)酯、己二醇·双(2-苯基咪唑基乙烷酸)酯、癸二醇·双(2-甲基咪唑基乙烷酸)酯、癸二醇·双(2-乙基-4-甲基咪唑基乙烷酸)酯、癸二醇·双(2-苯基咪唑基乙烷酸)酯、三环戊烷二甲醇·双(2-甲基咪唑基乙烷酸)酯、三环戊烷二甲醇·双(2-乙基-4-甲基咪唑基乙烷酸)酯、三环戊烷二甲醇·双(2-苯基咪唑基乙烷酸)酯、1-(2-羟基萘基甲基)-2-甲基咪唑、1-(2-羟基萘基甲基)-2-乙基-4-甲基咪唑、1-(2-羟基萘基甲基)-2-苯基咪唑和咪唑硅烷(例如四国化成工业制;2MUSIZ)等,它们也可以以与偏苯三酸、异氰脲酸及硼等的盐的形式使用。此外,也可以如上述胺系固化剂那样进行环氧改性而使用。
作为可用作(C)成分的固化剂的市售品,例如可列举出ADEKA HARDENER EH-3636AS、ADEKA HARDENER EH-4351S(株式会社艾迪科制;双氰胺型潜在性固化剂)、ADEKAHARDENER EH-5011S、ADEKA HARDENER EH-5046S(株式会社艾迪科制;咪唑型潜在性固化剂)、ADEKA HARDENER EH-4357S、ADEKA HARDENER EH-5057P、ADEKA HARDENER EH-5057PK(株式会社艾迪科制;多胺型潜在性固化剂)、Amicure PN-23、Amicure PN-40(AjinomotoFine-Techno制;胺加成系潜在性固化剂)、Amicure VDH(Ajinomoto Fine-Techno制;酰肼系潜在性固化剂)、Fujicure FXR-1020(T&K TOKA制;潜在性固化剂)、CUREZOL(四国化成工业制;咪唑系固化剂)、TS-G(四国化成工业制;聚硫醇系固化剂)、DPMP、PEMP(SC有机化学制;聚硫醇系固化剂)及PETG(淀化学制;聚硫醇系固化剂)等。
固化剂可以单独使用,也可以将2种以上并用。
本发明中使用的(C)成分的固化剂中,优选咪唑系固化剂,尤其是2-甲基咪唑、2-乙基-4-甲基咪唑等由于能够以比较少量的使用来固化,可获得与作为(A)成分的式(1)所表示的化合物的协同效应,因此优选。
作为本发明的(C)成分的固化剂的配合量没有特别限定,相对于作为(B)成分的环氧树脂100质量份,优选为0.01~100质量份,更优选为1~70质量份,进一步优选为1~50质量份,特别优选为3~30质量份。
在本发明中,可以根据需要将上述固化剂与公知的环氧树脂固化促进剂并用。作为固化促进剂,例如可列举出三苯基膦等膦类;四苯基溴化鏻等鏻盐;苄基二甲基胺和2,4,6-三(二甲基氨基甲基)苯酚等胺类;三甲基氯化铵等季铵盐类;3-(对氯苯基)-1,1-二甲基脲、3-(3,4-二氯苯基)-1,1-二甲基脲、3-苯基-1,1-二甲基脲、异佛尔酮二异氰酸酯-二甲基脲和甲苯二异氰酸酯-二甲基脲等脲类;三氟化硼与胺类的络合物、和三氟化硼与醚化合物的络合物等。这些固化促进剂可以单独使用,也可以将2种以上并用。环氧树脂固化促进剂的含量没有特别限制,可以根据固化性树脂组合物的用途而适当设定。
本发明的固化性树脂组合物含有上述式(1)所表示的化合物作为(A)成分,特别是含有上述式(1A)和/或(1B)所表示的化合物中的至少1种、尤其是上述式(1A-1)、(1B-1)、(1A-2)、(1B-2)、(1A-3)、(1B-3)、(1A-4)或(1B-4)所表示的化合物中的至少一种作为(A)成分由于可得到热稳定性及储存稳定性优异的固化性树脂组合物,因此优选,最优选含有(1A-1)或(1B-1)所表示的化合物中的至少一种。
(A)成分的含量相对于(C)成分100质量份,优选为1~2000质量份,更优选为10~1000质量份,进一步优选为30~1000质量份。若(A)成分的含量为1质量份以上,则能够得到固化性树脂组合物的稳定性赋予效果,若为2000质量份以下,则能够得到充分的固化性。
在固化性树脂组合物中,(A)成分的含量与(B)成分的合计量相对于组合物中的溶剂及填充剂以外的成分的合计量,适宜为5质量%以上,更适宜为10质量%以上,有时也为20质量%以上。
本发明的固化性树脂组合物可以含有填充剂。
作为上述填充剂,例如可列举出熔融二氧化硅及结晶二氧化硅等二氧化硅;氢氧化镁、氢氧化铝、钼酸锌、碳酸钙、碳酸硅、硅酸钙、钛酸钾、氧化铍、氧化锆、锆石、镁橄榄石、块滑石、尖晶石、莫来石及氧化钛等粉体、以及将它们球形化而得到的珠、玻璃纤维、纸浆纤维、合成纤维及陶瓷纤维等纤维等。
本发明的固化性树脂组合物可以含有各种溶剂。
作为上述有机溶剂,例如可列举出四氢呋喃、1,2-二甲氧基乙烷及1,2-二乙氧基乙烷等醚类;异丁醇、正丁醇、异丙醇、正丙醇、戊基醇、苄基醇、糠醇及四氢糠醇等醇类;甲乙酮、甲基异丙基酮及甲基丁基酮等酮类;苯、甲苯及二甲苯等芳香族烃;三乙基胺、吡啶、二噁烷及乙腈等。
本发明的固化性树脂组合物可以根据需要含有其他的各种添加剂。
作为上述添加剂,可列举出γ-氨基丙基三乙氧基硅烷、N-β-(氨基乙基)-γ-氨基丙基三乙氧基硅烷、N-β-(氨基乙基)-N’-β-(氨基乙基)-γ-氨基丙基三乙氧基硅烷、γ-苯胺基丙基三乙氧基硅烷、γ-环氧丙氧基丙基三乙氧基硅烷、β-(3,4-环氧环己基)乙基三乙氧基硅烷、乙烯基三乙氧基硅烷、N-β-(N-乙烯基苄基氨基乙基)-γ-氨基丙基三乙氧基硅烷、γ-甲基丙烯酰氧基丙基三甲氧基硅烷、γ-氯丙基三甲氧基硅烷和γ-巯基丙基三甲氧基硅烷等硅烷偶联剂;联苯酚等酚类化合物;单烷基缩水甘油醚等反应性稀释剂;邻苯二甲酸二辛酯、邻苯二甲酸二丁酯、苄基醇和煤焦油等非反应性的稀释剂(增塑剂);玻璃布、芳纶布、碳纤维等增强材料;颜料;小烛树蜡、巴西棕榈蜡、木蜡、白蜡、蜂蜡、羊毛脂、鲸蜡、褐煤蜡、石油蜡、脂肪族蜡、脂肪族酯、脂肪族醚、芳香族酯和芳香族醚等润滑剂;增稠剂;触变剂;消泡剂;防锈剂;磷系、酚系及硫系抗氧化剂;紫外线吸收剂;受阻胺系稳定剂;胶体二氧化硅及胶体氧化铝等常用的添加剂。本发明中,也可以进一步并用氰酸酯树脂、二甲苯树脂及石油树脂等粘合性的树脂类。
本发明的固化性树脂组合物由于含有特定的化合物,因此可以制成储存稳定性优异、并且固化物的热稳定性优异的组合物。即,认为本发明的化合物由于具有以酰亚胺骨架作为中心的特定结构,因此与固化剂作用而储存稳定性提高,由于具有环氧基,因此在固化后没有游离,因此不会降低固化物的热稳定性。本发明的固化性树脂组合物可以作为单组分固化型的固化性树脂组合物而适宜地使用。作为本发明的固化性树脂组合物的用途,没有特别限制,例如可列举出电子部件粘接剂、电子部件密封材、浇铸材、涂料及结构粘接剂等。
实施例
接着,通过实施例及比较例对本发明进一步进行详细说明,但本发明不受这些实施例的任何限定。
〔实施例1〕
在安装有迪安-斯塔克(Dean-Stark)管和李比希冷却器的50mL的二口烧瓶中添加邻苯二甲酸酐(1.4904g、10.062mmol)和2-氨基乙烷硫醇(0.7766g、10.066mmol)后,添加甲苯(10mL)而进行加热回流。16小时后,空气冷却后将反应溶液用蒸发器浓缩。通过将所得到的混合物利用硅胶柱色谱法进行精制(己烷/乙酸乙酯=3/1(体积比)),以淡黄色的固体得到硫醇化合物(1.9237g、9.282mmol、收率92%)。
在50mL的二口烧瓶中添加上述中得到的硫醇化合物(1.0359g、4.998mmol)和AIBN(2,2’-偶氮双异丁腈、41.8mg、0.25mmol)而设定为氮气氛。之后,添加通过减压操作而除去了残存氧的N,N-二甲基甲酰胺(5mL)而制成均匀的溶液后,添加烯丙基缩水甘油醚(0.5827g、5.105mmol),将所得到的溶液在70℃下加热,由此进行反应。16小时后,空气冷却后将反应溶液用蒸发器浓缩。通过将所得到的混合物利用硅胶柱色谱法进行精制(己烷/乙酸乙酯=3/1~2/1体积比),以淡黄色的液体得到环氧酰亚胺(1.3525g、4.185mmol、收率84%)。
将所得到的淡黄色的液体的1H-NMR测定结果示于图1中。作为测定溶剂,使用了氘代氯仿。
由这些结果,确认所得到的淡黄色的液体为图1中记载的化合物1A-1与化合物1B-1〔质量比87/13〕的混合物(以下,记载为“EP-IMIDE”。)。
〔实施例2〕
通过在样品瓶中添加ADEKA RESIN EP-4100L(株式会社艾迪科制;双酚A型环氧树脂)(BADGE)613.1mg(1.801mmol)与实施例1中得到的化合物的混合物(EP-IMIDE)194.5mg(0.6052mmol)及2-乙基-4-甲基咪唑(EMI)22.0mg(0.1997mmol)并混合,调整液状的固化性树脂组合物。
将上述固化性树脂组合物的一部分(10mg)转移至铝盘中,以130℃、3小时使其固化,使用所得到的固化物在升温速度10℃、氮气氛下进行热重量分析。
此外,将上述固化性树脂组合物在暗处、室温下保存,通过确认组合物的流动性来评价储存稳定性。将结果示于表1中。需要说明的是,表1中的配合比为将环氧树脂的摩尔数设定为100时的摩尔比。
〔比较例1〕BADGE:EMI=100:5
通过在样品瓶中添加ADEKA RESIN EP-4100L(株式会社艾迪科制;双酚A型环氧树脂)(BADGE)680.3mg(1.998mmol)及EMI(22.0mg,0.1997mmol)并混合,制备液状的固化性树脂组合物。
〔评价1:热稳定性〕
将上述固化性树脂组合物的一部分(8mg)转移至铝盘中,以130℃、3小时使其固化,使用所得到的固化物在升温速度10℃、氮气氛下进行热重量分析。将5%重量减少温度超过300℃的情况判断为合格(A),将其示于表1中。
此外将上述固化性树脂组合物在暗处、室温下保存,通过确认组合物的流动性来评价储存稳定性。将结果示于表1中。
〔评价2:储存稳定性〕
将固化性树脂组合物以液面位于距离瓶下为五分之一的高度的量放入直径为13mm、高度为40mm的玻璃瓶中,盖上盖子。将其在桌子上倾斜90°,观察1分钟后的状态,确认是否具有流动性。在固化性树脂组合物的形状中见到变化的情况下设定为具有流动性,没有变化的情况下设定为没有流动性。每放置1天进行评价,在流动性消失的时刻结束评价。将可维持流动性的天数示于表1中。在能够维持3天以上流动性的情况下,判断为储存稳定性合格(A),不满足其的情况下判断为储存稳定性不合格(B)。
表1
由上述评价结果可知,通过使用本发明的化合物即EP-IMIDE,与不添加酰亚胺化合物的情况同等地固化物的热稳定性优异,并且与不添加酰亚胺化合物的情况相比,储存稳定性提高5天。
产业上的可利用性
根据本发明,特别提供储存稳定性优异的单组分固化型的固化性树脂组合物,例如可以适宜用于电子部件粘接剂、电子部件密封材、浇铸材、涂料、结构粘接剂等。
Claims (7)
1.一种化合物,其以下述式(1)表示,
式(1)中,R1表示氢原子或甲基,R2、R3、R4及R5分别独立地表示氢原子、碳数1~10的烷基、碳数1~10的烷氧基、碳数1~10的烷酰氧基、碳数1~10的烷氧基羰基、碳数1~10的烷基酰胺基、碳数1~10的酰基氨基、卤素原子、羟基、硝基或腈基,A1表示碳数1~20的亚烷基,A2表示亚丙基或异亚丙基。
2.根据权利要求1所述的化合物,其以下述式(1A)或(1B)表示,
所述式(1A)中,R1a表示氢原子或甲基,R6表示氢原子、碳数1~4的烷基、卤素原子、羟基或硝基,
所述式(1B)中,R1b表示氢原子或甲基,R7表示氢原子、碳数1~4的烷基、卤素原子、羟基或硝基。
3.一种固化性树脂组合物,其含有作为(A)成分的权利要求1或2所述的化合物、作为(B)成分的环氧树脂、及作为(C)成分的固化剂。
4.根据权利要求3所述的固化性树脂组合物,其中,作为(C)成分的固化剂含有咪唑系固化剂。
5.根据权利要求3或4所述的固化性树脂组合物,其中,作为(A)成分的化合物的含量相对于作为(C)成分的固化剂100质量份为1~2000质量份,作为(C)成分的固化剂的含量相对于作为(B)成分的环氧树脂100质量份为0.01~100质量份。
6.根据权利要求3~5中任一项所述的固化性树脂组合物,其为单组分固化型。
7.权利要求3~6中任一项所述的固化性树脂组合物的固化物。
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