TW202128811A - 樹脂組合物 - Google Patents
樹脂組合物 Download PDFInfo
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- TW202128811A TW202128811A TW109142429A TW109142429A TW202128811A TW 202128811 A TW202128811 A TW 202128811A TW 109142429 A TW109142429 A TW 109142429A TW 109142429 A TW109142429 A TW 109142429A TW 202128811 A TW202128811 A TW 202128811A
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- resin composition
- compound
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- amine
- resin
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- 239000011342 resin composition Substances 0.000 title claims abstract description 54
- -1 cardanol compound Chemical class 0.000 claims abstract description 117
- 150000001412 amines Chemical class 0.000 claims abstract description 56
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 claims abstract description 37
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 claims abstract description 37
- FAYVLNWNMNHXGA-UHFFFAOYSA-N Cardanoldiene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1 FAYVLNWNMNHXGA-UHFFFAOYSA-N 0.000 claims abstract description 37
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 claims abstract description 37
- 229920005989 resin Polymers 0.000 claims abstract description 34
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- 229920000647 polyepoxide Polymers 0.000 claims abstract description 28
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims abstract description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 17
- 239000004643 cyanate ester Substances 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 239000004593 Epoxy Substances 0.000 claims description 25
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- 239000004849 latent hardener Substances 0.000 claims description 18
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical class OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000005011 phenolic resin Substances 0.000 claims description 13
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- 229920000768 polyamine Polymers 0.000 claims description 7
- 239000000853 adhesive Substances 0.000 claims description 6
- 230000001070 adhesive effect Effects 0.000 claims description 6
- 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 claims description 6
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- 229920000570 polyether Polymers 0.000 claims description 5
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
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- 229910052717 sulfur Inorganic materials 0.000 claims description 2
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
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- 125000003118 aryl group Chemical group 0.000 description 14
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 239000000805 composite resin Substances 0.000 description 6
- 125000003367 polycyclic group Chemical group 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
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- 238000006243 chemical reaction Methods 0.000 description 5
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- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
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- 125000000753 cycloalkyl group Chemical group 0.000 description 4
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- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
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- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
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- 238000007789 sealing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- 229940084106 spermaceti Drugs 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-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
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-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
- 239000002023 wood Substances 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G59/20—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 characterised by the epoxy compounds used
-
- 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
- C08G59/40—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 characterised by the curing agents used
- C08G59/50—Amines
- C08G59/56—Amines together with other curing agents
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- 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
- C08G59/40—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 characterised by the curing agents used
- C08G59/62—Alcohols or phenols
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- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
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- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J201/00—Adhesives based on unspecified macromolecular compounds
- C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
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Abstract
本發明之課題在於提供一種能夠迅速硬化，且可獲得低彈性之硬化物之樹脂組合物。
本發明之樹脂組合物含有(A)氰酸酯樹脂、(B)腰果酚化合物或其縮水甘油醚、(C)胺系潛在性硬化劑及(D)環氧樹脂(但，腰果酚化合物之聚縮水甘油醚除外)。上述樹脂組合物中，腰果酚化合物及其縮水甘油醚之含量相對於(A)成分100質量份，較佳為50～5000質量份。上述(C)成分較佳為具有活性氫之胺系潛在性硬化劑。
Description
本發明係關於一種樹脂組合物。
環氧樹脂組合物於工業上廣泛地用於塗料、接著劑、各種成形材料等。
於僅單獨使用或混合使用現有之環氧樹脂時不充分之情形時等，混合環氧樹脂與氰酸酯樹脂而成之氰酸酯-環氧複合樹脂組合物由於耐熱性較高，故多用作有用之材料。
例如，專利文獻1中提出有一種半導體密封用液狀環氧樹脂組合物，其包含氰酸酯樹脂、環氧樹脂、無機填充劑、金屬螯合物及二醯肼化合物等。專利文獻2中提出有一種複合組合物，其含有氰酸酯樹脂、環氧樹脂、及胺系硬化劑。專利文獻3中提出有一種熱硬化性樹脂組合物，其含有氰酸酯樹脂、環氧樹脂、及包含咪唑成分之潛在性硬化劑。專利文獻4中提出有一種複合樹脂，其係含有氰酸酯樹脂、環氧樹脂及含有二烷基胺基烷基胺之潛在性硬化劑而成。然而，利用該等專利文獻中所提出之氰酸酯-環氧複合樹脂組合物僅可獲得較硬之硬化物。
另一方面，已知業界將腰果酚或其縮水甘油醚用於環氧樹脂組合物(參照專利文獻5～8)。然而，該等專利文獻中未記載組合腰果酚或其縮水甘油醚與氰酸酯-環氧複合樹脂組合物，甚至未提示藉由該組合，由樹脂組合物獲得之硬化物之彈性會降低。
[先前技術文獻]
[專利文獻]
專利文獻1：US6469074B1
專利文獻2：日本專利特開昭60-250026號公報
專利文獻3：US6342577B1
專利文獻4：日本專利特開2009-13205號公報
專利文獻5：US2003/62911A1
專利文獻6：WO03/075338A1
專利文獻7：WO2004/078870A1
專利文獻8：US2009/203813A1
[發明所欲解決之問題]
因此，本發明所欲解決之問題在於提供一種可獲得低彈性之硬化物，且能夠迅速硬化之樹脂組合物。
[解決問題之技術手段]
本發明者等人為了解決上述問題而進行了努力研究，結果發現，根據含有氰酸酯樹脂、環氧樹脂、潛在性硬化劑及腰果酚化合物或其縮水甘油醚而成之樹脂組合物，可解決上述問題，從而完成本發明。
即，本發明係一種樹脂組合物，其含有(A)氰酸酯樹脂、(B)腰果酚化合物或其縮水甘油醚、(C)胺系潛在性硬化劑及(D)環氧樹脂(但，腰果酚化合物之聚縮水甘油醚除外)。
[發明之效果]
根據本發明，提供一種能夠迅速硬化，且可獲得低彈性之硬化物之樹脂組合物。本發明之樹脂組合物可適宜地用於接著劑等用途。
以下，對本發明之樹脂組合物進行說明。
本發明之樹脂組合物含有(A)氰酸酯樹脂、(B)腰果酚化合物或其縮水甘油醚、(C)胺系潛在性硬化劑及(D)環氧樹脂(但，腰果酚化合物之聚縮水甘油醚除外)。
首先，對本發明之樹脂組合物中所含之(A)成分進行說明。於本發明中，作為(A)成分之氰酸酯樹脂可無特別限制地使用具有2個以上氰酸酯基之化合物，且其分子結構或分子量等並無特別限制。
作為氰酸酯樹脂，較佳為使用選自由下述式(1)所表示之化合物、下述式(2)所表示之化合物、及該等之預聚物所組成之群中之至少1種。於本發明中，所謂預聚物係指化合物進行自聚合而成者、或利用任意微量成分略微進行聚合而成者。
NC-O-A1
-Y1
-A2
-O-CN (1)
式中，Y1
表示未經取代或經氟取代之二價烴基、-O-、-S-、或單鍵，
A1
及A2
分別獨立地表示未經取代或經1～4個烷基取代之伸苯基。
作為上述式(1)中之Y1
所表示之二價烴基，例如可列舉：伸烷基、伸環烷基、伸環烷基伸烷基、伸芳基及伸芳基伸烷基等。於本發明中，就容易獲取，且物性優異之方面而言，Y1
較佳為伸烷基。
上述伸烷基可為直鏈狀，亦可為支鏈狀。作為直鏈狀之伸烷基，可列舉碳數1～20者。作為其具體例，可列舉自甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十四烷基、十六烷基、十八烷基及二十烷基等直鏈狀之烷基之末端的碳原子去除1個氫原子所得之二價基。另一方面，作為支鏈狀之伸烷基，可列舉碳數1～20者。作為其具體例，可列舉自異丙基、異丁基、第二丁基、第三丁基、異戊基、第三戊基、異辛基、2-乙基己基、第三辛基、異壬基及異癸基等支鏈狀之伸烷基去除1個氫原子所得之二價基。於本發明中，就容易獲取，且物性優異之方面而言，伸烷基之碳數較佳為1～10，更佳為1～8，進而較佳為1～4。
上述伸環烷基可為單環式，亦可為多環式。作為單環式伸環烷基，可列舉碳數3～20者。作為其具體例，可列舉自環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基、環十一烷基、環十二烷基、環十三烷基、環十四烷基、環十五烷基、環十六烷基、環十七烷基、環十八烷基、環十九烷基及環二十烷基等單環式環烷基去除1個氫原子所得之二價基。作為多環式烷基，可列舉碳數8～14者。作為其具體例，可列舉自金剛烷基、十氫萘基、八氫并環戊二烯、雙環[1.1.1]戊基及十四氫蒽基等多環式烷基去除1個氫原子所得之二價基。
於本發明中，所謂伸環烷基伸烷基係1個以上之伸烷基與1個以上之伸環烷基組合而成之二價基。上述伸環烷基伸烷基中之伸環烷基可為單環式，亦可為多環式。作為單環式伸環烷基伸烷基，可列舉自上述烷基之1個或2個以上之氫原子被取代為上述單環式環烷基而成之基去除1個氫原子所得之二價基、或自該單環式環烷基之2個以上之氫原子被取代為上述烷基而成之基去除1個氫原子所得之二價基。作為多環式伸環烷基伸烷基，可列舉自上述烷基之1個或2個以上之氫原子被取代為上述多環式環烷基而成之基去除1個氫原子所得之二價基、或自該多環式環烷基之2個以上之氫原子被取代為上述烷基而成之基去除1個氫原子所得之二價基。
上述伸芳基可為單環式，亦可為縮合環式。作為單環式伸芳基，可列舉碳數6～20者。作為其具體例，可列舉自苯基及聯苯基等單環式芳基去除1個氫原子所得之二價基。作為縮合環式伸芳基伸烷基，可列舉碳數10～18者。作為其具體例，可列舉自萘基、蒽基、菲基、及茀等縮合環式芳基去除1個氫原子所得之二價基。
於本發明中，所謂伸芳基伸烷基係1個以上之伸烷基與1個以上之伸芳基組合而成之二價基。上述伸芳基伸烷基中之伸芳基可為單環式，亦可為縮合環式。作為單環式伸芳基伸烷基，可列舉自上述烷基之1個或2個以上之氫原子被取代為上述單環式芳基而成之基去除1個氫原子所得之二價基、或自該單環式芳基之2個以上之氫原子被取代為上述烷基而成之基去除1個氫原子所得之二價基。作為縮合環式伸芳基伸烷基，可列舉自上述烷基之1個或2個以上之氫原子被取代為上述縮合環式芳基而成之基去除1個氫原子所得之二價基、或自該縮合環式芳基之2個以上之氫原子被取代為上述烷基而成之基去除1個氫原子所得之二價基。
就容易獲取，且物性優異之方面而言，上述式(1)中之Y1
所表示之二價烴基較佳為包含選自由下述式(Y-1)～(Y-10)所組成之群中之基。所謂「包含選自由式(Y-1)～(Y-10)所組成之群中之基」，係指Y1
僅包含選自由(Y-1)～(Y-10)所組成之群中之1個基、或包含選自由(Y-1)～(Y-10)所組成之群中之2個以上之基連結而成之基。
[化1]
式中，n表示4～12之整數，
R3
、R4
、R5
及R6
分別獨立地表示氫原子或者未經取代或經氟取代之甲基，
*表示鍵結鍵。
取代式(1)中之A1
及A2
所表示之伸苯基之烷基可為直鏈狀，亦可為支鏈狀。作為直鏈狀之烷基，可列舉碳數1～20者。作為其具體例，可列舉：甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十四烷基、十六烷基、十八烷基及二十烷基等。作為支鏈狀之烷基，可列舉碳數1～20者。作為其具體例，可列舉：異丙基、異丁基、第二丁基、第三丁基、異戊基、第三戊基、異辛基、2-乙基己基、第三辛基、異壬基及異癸基等。
[化2]
式中，m表示1以上之整數，
Y2
表示硫原子、未經取代或經氟取代之二價烴基，複數個Y2
可相同亦可不同，
R1
及R2
分別獨立地表示氫原子或碳數1～4之烷基。
作為式(2)中之R1
及R2
所表示之碳數1～4之烷基，可列舉：甲基、乙基、丙基及丁基等直鏈烷基、以及異丙基、第二丁基、第三丁基及異丁基甲基等支鏈烷基。
作為上述式(2)中之Y2
所表示之二價烴基，可列舉與式(2)中之Y1
所表示之二價烴基相同者。
作為上述式(2)中之Y2
，就容易獲取，且物性優異之方面而言，較佳為包含選自由上述式(Y-1)～(Y-10)所組成之群中之基。
上述式(2)中之m表示1以上之整數。於本發明中，m之上限值可設為10以下。
其次，對本發明之樹脂組合物中所含之(B)成分之腰果酚化合物及其縮水甘油醚進行說明。於本發明中，所謂腰果酚化合物係由腰果等獲得之經具有不飽和鍵之鏈式烴基取代之1種酚。該腰果酚化合物中所含之鏈式烴基中之不飽和鍵之數量可為1個，可為2個，亦可為3個。作為具有1個不飽和鍵之鏈式烴基之具體例，可列舉8-十五烯基。作為具有2個不飽和鍵之鏈式烴基之具體例，可列舉7,10-十五二烯基及8,11-十五二烯基。作為具有2個不飽和鍵之鏈式烴基之具體例，可列舉8,11,14-十五三烯基。於本發明中，腰果酚化合物中之鏈式烴基較佳為具有2個不飽和鍵。其具體例較佳為下述式(a-1)所表示者。如上所述，腰果酚化合物係自腰果等天然物提取者，故不易獲得純度較高者。因此，包含10質量%以下之雜質者亦包含於本發明中所使用之腰果酚化合物中。腰果酚化合物之縮水甘油醚可為單縮水甘油醚，亦可為聚縮水甘油醚。於本發明中，就所獲得之硬化物之彈性進一步降低之方面而言，較佳為使用腰果酚化合物、或其單縮水甘油醚，更佳為使用腰果酚化合物之單縮水甘油醚。
[化3]
腰果酚化合物之縮水甘油醚可藉由在利用酚化合物製造縮水甘油醚之情形時所使用之公知之方法而製造。腰果酚化合物之縮水甘油醚可為如下述式所表示之多官能體。
[化4]
[化5]
式中，G表示羥基或下述基(i)，p表示0～10之數。
[化6]
作為上述腰果酚化合物及其縮水甘油醚，可使用市售品。作為市售品，例如可列舉：Cardolite NX-2021(Cardolite公司製造；腰果酚)、Cardolite NX-2022(Cardolite公司製造；高純度腰果酚)、Cardolite NX-2023D(Cardolite公司製造；深色、顏色穩定之腰果酚)、Cardolite NX-2023(Cardolite公司製造；明亮之色相、顏色穩定之腰果酚)、Cardolite NX-2024(Cardolite公司製造；固定週期、標準純度腰果酚)、Cardolite NX-2025(Cardolite公司製造；高純度腰果酚)、Cardolite Ultra LITE NX-2023(明亮之色相、顏色穩定之腰果酚)、Cardolite NC-513(Cardolite公司製造；腰果酚單縮水甘油醚)、Ultra LITE 513(Cardolite公司製造；明亮之色相、低黏度腰果酚單縮水甘油醚)、NC-514(Cardolite公司製造；聚腰果酚聚縮水甘油醚)、NC-514S(Cardolite公司製造；低黏度聚腰果酚聚縮水甘油醚)、NC-547(Cardolite公司製造；聚腰果酚聚縮水甘油醚)等。
本發明之樹脂組合物中之上述腰果酚化合物及其縮水甘油醚之含量並無特別限定，較佳為(A)成分之氰酸酯樹脂及下述(D)成分之環氧化合物之合計量的5～50質量%，更佳為10～30質量%。若腰果酚化合物及其縮水甘油醚之含量為5質量%以上，則所獲得之硬化物之彈性降低，若為50質量%以下，則接著性進一步增高，故而較佳。
於本發明中，就所獲得之硬化物之彈性進一步降低之方面而言，相對於(A)成分之氰酸酯樹脂100質量份，較佳為含有腰果酚化合物及其縮水甘油醚之含量10～1000質量份，更佳為含有20～500質量份。
其次，對本發明之樹脂組合物中所含之(C)成分進行說明。作為胺系潛在性硬化劑，例如可列舉：乙二醯肼、丙二醯肼、琥珀二醯肼、戊二醯肼、己二醯肼、辛二醯肼、壬二醯肼、癸二醯肼及鄰苯二甲二醯肼等二元酸二醯肼；苯并胍胺及乙胍𠯤等胍胺；雙氰胺；三聚氰胺；以及胺化合物與羧酸之脫水縮合物、胺化合物與環氧化合物之加成物、胺化合物與異氰酸酯化合物之加成物、胺化合物之麥可加成物、胺化合物之曼尼希反應物、胺化合物與脲之縮合物、胺化合物與酮之縮合物等改性胺等。該等胺系潛在性硬化劑可單獨使用一種，亦可併用兩種以上。於本發明中，就樹脂組合物之反應性變得良好之方面而言，作為(C)成分，較佳為使用具有活性氫者。作為具有活性氫之胺系潛在性硬化劑，例如可列舉：二元酸二醯肼、胍胺及下述改性胺。
於本發明中，就容易調整物性之方面而言，亦較佳為使用改性胺。作為改性胺，較佳為使用選自由下述(C-1)～(C-2)所組成之群中之至少1種。
(C-1)使具有1個以上活性氫之胺化合物與環氧化合物反應而成之改性胺。
(C-2)使具有1個以上活性氫之胺化合物與異氰酸酯化合物反應而成之改性胺。
(C-3)使具有1個以上活性氫之胺化合物、環氧化合物、及異氰酸酯化合物反應而成之改性胺。
作為上述具有1個以上活性氫之胺化合物，例如可列舉：聚醚三胺、聚醚二胺、聚氧化丙烯二胺、聚四氫呋喃二胺、聚氧化丙烯三胺等聚醚聚胺；乙二胺、1,2-二胺基丙烷、1,3-二胺基丙烷、1,3-二胺基丁烷、1,4-二胺基丁烷、六亞甲基二胺等伸烷基二胺類；二伸乙基三胺、三伸乙基三胺、四伸乙基五胺等聚烷基聚胺類；1,4-二胺基環己烷、1,3-二胺基環己烷、1,3-二胺基甲基環己烷、1,2-二胺基環己烷、1,4-二胺基-3,6-二乙基環己烷、4,4'-二胺基二環己基甲烷、1,3-雙(胺基甲基)環己烷、1,4-雙(胺基甲基)環己烷、4,4'-二胺基二環己基丙烷、雙(4-胺基環己基)碸、4,4'-二胺基二環己醚、2,2'-二甲基-4,4'-二胺基二環己基甲烷、異佛爾酮二胺、降莰烯二胺等脂環式聚胺類；間苯二甲胺、二胺基二苯甲烷、二胺基二苯基碸、二乙基甲苯二胺、1-甲基-3,5-二乙基-2,4-二胺基苯、1-甲基-3,5-二乙基-2,6-二胺基苯、1,3,5-三乙基-2,6-二胺基苯、3,3'-二乙基-4,4'-二胺基二苯甲烷、3,5,3',5'-四甲基-4,4'-二胺基二苯甲烷等芳香族聚胺類；苯并胍胺、乙胍𠯤等胍胺類；2-甲基咪唑、2-乙基-4-甲基咪唑、2-異丙基咪唑、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-胺基丙基咪唑等咪唑類；乙二醯肼、丙二醯肼、琥珀二醯肼、戊二醯肼、己二醯肼、辛二醯肼、壬二醯肼、癸二醯肼、鄰苯二甲二醯肼等二醯肼類；N,N-二甲基胺基乙基胺、N,N-二乙基胺基乙基胺、N,N-二異丙基胺基乙基胺、N,N-二烯丙基胺基乙基胺、N,N-苄基甲基胺基乙基胺、N,N-二苄基胺基乙基胺、N,N-環己基甲基胺基乙基胺、N,N-二環己基胺基乙基胺、N-(2-胺基乙基)吡咯啶、N-(2-胺基乙基)哌啶、N-(2-胺基乙基)嗎啉、N-(2-胺基乙基)哌𠯤、N-(2-胺基乙基)-N'-甲基哌𠯤、N,N-二甲基胺基丙基胺、N,N-二乙基胺基丙基胺、N,N-二異丙基胺基丙基胺、N,N-二烯丙基胺基丙基胺、N,N-苄基甲基胺基丙基胺、N,N-二苄基胺基丙基胺、N,N-環己基甲基胺基丙基胺、N,N-二環己基胺基丙基胺、N-(3-胺基丙基)吡咯啶、N-(3-胺基丙基)哌啶、N-(3-胺基丙基)嗎啉、N-(3-胺基丙基)哌𠯤、N-(3-胺基丙基)-N'-甲基哌啶、4-(N,N-二甲基胺基)苄基胺、4-(N,N-二乙基胺基)苄基胺、4-(N,N-二異丙基胺基)苄基胺、N,N-二甲基異佛爾酮二胺、N,N-二甲基二胺基環己烷、N,N,N'-三甲基乙二胺、N'-乙基-N,N-二甲基乙二胺、N,N,N'-三甲基乙二胺、N'-乙基-N,N-二甲基丙二胺、N'-乙基-N,N-二苄基胺基丙基胺；N,N-(二胺基丙基)-N-甲基胺、N,N-二胺基丙基乙基胺、N,N-二胺基丙基丙基胺、N,N-二胺基丙基丁基胺、N,N-二胺基丙基戊基胺、N,N-二胺基丙基己基胺、N,N-二胺基丙基-2-乙基己基胺、N,N-二胺基丙基環己基胺、N,N-二胺基丙基苄基胺、N,N-二胺基丙基烯丙基胺、雙[3-(N,N-二甲基胺基丙基)]胺、雙[3-(N,N-二乙基胺基丙基)]胺、雙[3-(N,N-二異丙基胺基丙基)]胺、雙[3-(N,N-二丁基胺基丙基)]胺等。
作為上述環氧化合物，例如可列舉：對苯二酚、間苯二酚、兒茶酚、間苯三酚等單核多酚化合物之聚縮水甘油醚化合物；二羥基萘、聯苯酚、亞甲基雙酚(雙酚F)、亞甲基雙(鄰甲酚)、亞乙基雙酚、亞異丙基雙酚(雙酚A)、亞異丙基雙(鄰甲酚)、四溴雙酚A、1,3-雙(4-羥基異丙苯基苯)、1,4-雙(4-羥基異丙苯基苯)、1,1,3-三(4-羥基苯基)丁烷、1,1,2,2-四(4-羥基苯基)乙烷、硫代雙酚、磺醯基雙酚、氧基雙酚、苯酚酚醛清漆、鄰甲酚酚醛清漆、乙基苯酚酚醛清漆、丁基苯酚酚醛清漆、辛基苯酚酚醛清漆、間苯二酚酚醛清漆、萜酚等多核多酚化合物之聚縮水甘油醚化合物；乙二醇、丙二醇、丁二醇、己二醇、聚二醇、硫代雙乙醇、甘油、三羥甲基丙烷、季戊四醇、山梨糖醇、雙酚A-環氧烷加成物等多元醇類之聚縮水甘油醚；順丁烯二酸、反丁烯二酸、伊康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸、三聚酸、鄰苯二甲酸、間苯二甲酸、對苯二甲酸、偏苯三甲酸、1,3,5-苯三甲酸、均苯四甲酸、四氫鄰苯二甲酸、六氫鄰苯二甲酸、內亞甲基四氫鄰苯二甲酸等脂肪族、芳香族或脂環族多元酸之縮水甘油酯類、及甲基丙烯酸縮水甘油酯之均聚物或共聚物；N,N-二縮水甘油基苯胺、雙(4-(N-甲基-N-縮水甘油基胺基)苯基)甲烷、二縮水甘油基鄰甲苯胺等具有縮水甘油基胺基之環氧化合物；乙烯基環己烯二環氧化物、二環戊二烯二環氧化物、3,4-環氧環己烷羧酸3,4-環氧環己基甲酯、6-甲基環己烷羧酸3,4-環氧-6-甲基環己基甲酯、己二酸雙(3,4-環氧-6-甲基環己基甲基)酯等環狀烯烴化合物之環氧化物；環氧化聚丁二烯、環氧化苯乙烯-丁二烯共聚物等環氧化共軛二烯聚合物、異氰尿酸三縮水甘油酯等雜環化合物。
作為上述多異氰酸酯化合物，例如可列舉：2,4-甲苯二異氰酸酯、2,6-甲苯二異氰酸酯、二苯甲烷-4,4'-二異氰酸酯、苯二異氰酸酯、苯二甲基二異氰酸酯、四甲基苯二甲基二異氰酸酯、1,5-萘二異氰酸酯、1,5-四氫萘二異氰酸酯、3,3'-二甲基二苯基-4,4'-二異氰酸酯、聯大茴香胺二異氰酸酯、四甲基苯二甲基二異氰酸酯等芳香族二異氰酸酯；異佛爾酮二異氰酸酯、二環己基甲烷-4,4'-二異氰酸酯、反-1,4-環己基二異氰酸酯、降莰烯二異氰酸酯等脂環式二異氰酸酯；四亞甲基二異氰酸酯、1,6-六亞甲基二異氰酸酯、2,2,4及/或(2,4,4)-三甲基六亞甲基二異氰酸酯、離胺酸二異氰酸酯等脂肪族二異氰酸酯；上述所例示之二異氰酸酯之異氰尿酸酯三聚化物、縮二脲三聚化物、三羥甲基丙烷加成化物等；三苯甲烷三異氰酸酯、1-甲基苯-2,4,6-三異氰酸酯、二甲基三苯甲烷四異氰酸酯等。進而該等異氰酸酯化合物能夠以碳二醯亞胺改性、異氰尿酸酯改性、縮二脲改性等形式使用，亦能夠以利用各種封端劑進行封端後之封端異氰酸酯之形式使用。
作為(C-1)之改性胺較佳為使具有1個以上活性氫之胺化合物與環氧化合物以相對於胺化合物之N-H基1當量，環氧化合物之環氧基成為0.1～1.1當量之量、尤其是成為0.2～1.0當量之量進行反應而成者。藉由使用該改性胺，可獲得保存穩定性及硬化性良好之樹脂組合物，故而較佳。
作為(C-2)之改性胺較佳為使具有1個以上活性氫之胺化合物與異氰酸酯化合物以相對於胺化合物之N-H基1當量，異氰酸酯化合物之異氰酸基成為0.1～1.1當量之量、尤其是成為0.2～1.0當量之量進行反應而成者。藉由使用該改性胺，可獲得保存穩定性及硬化性良好之樹脂組合物，故而較佳。
作為(C-3)之改性胺較佳為使具有1個以上活性氫之胺化合物、作為(C-2)之環氧化合物、及作為(C-3)之異氰酸酯化合物以相對於胺化合物之N-H基1當量，環氧化合物之環氧基成為0.1～1.0當量之量、尤其是成為0.2～1.0當量之量，多異氰酸酯化合物之異氰酸基成為0.01～0.9當量之量、尤其是成為0.05～0.8當量之量進行反應而成者。藉由使用該改性胺，可獲得保存穩定性及硬化性良好之樹脂組合物，故而較佳。
上述作為(C-1)、(C-2)及(C-3)之改性胺之製造方法並無特別限定，視需要可藉由使用溶劑，於常溫～140℃之加熱下進行1～10小時反應而製造。
於(C-3)改性胺中，通常較佳為於使胺化合物與環氧化合物反應後與多異氰酸酯化合物反應。
於使用溶劑之情形時，可於反應結束後，在加熱下藉由常壓或減壓去除溶劑。
又，於該等者中，固體者亦可使用噴射磨機等粉碎機進行粉碎。
作為上述改性胺之製造中所使用之上述溶劑，可列舉：甲基乙基酮、甲基戊基酮、二乙基酮、丙酮、甲基異丙基酮、丙二醇單甲醚乙酸酯、環己烷等酮類；四氫呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、丙二醇單甲醚等醚類；乙酸乙酯、乙酸正丁酯等酯類；苯、甲苯、二甲苯等芳香族烴；四氯化碳、氯仿、三氯乙烯、二氯甲烷等鹵代脂肪族烴；氯苯等鹵代芳香族烴。
於本發明之樹脂組合物中，於作為(C)成分之胺系潛在性硬化劑使用上述選自由(C-1)～(C-3)所組成之群中之至少1種改性胺之情形時，就可調整反應性之觀點而言，亦較佳為組合使用選自由(C-1)～(C-3)所組成之群中之至少1種改性胺與(E)酚樹脂。
作為上述酚樹脂，例如可列舉：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性酚樹脂、二環戊二烯酚加成型樹脂、苯酚芳烷基樹脂(ZYLOCK樹脂)、萘酚芳烷基樹脂、三酚基甲烷樹脂、四酚基乙烷樹脂、萘酚酚醛清漆樹脂、萘酚-苯酚共縮合酚醛清漆樹脂、萘酚-甲酚共縮合酚醛清漆樹脂、聯苯改性酚樹脂(以雙亞甲基連結酚核之多酚化合物)、聯苯改性萘酚樹脂(以雙亞甲基連結酚核之多元萘酚化合物)、胺基三𠯤改性酚樹脂(分子結構中具有酚骨架、三𠯤環及一級胺基之化合物)、及含烷氧基之芳香環改性酚醛清漆樹脂(以甲醛連結酚核及含烷氧基之芳香環之多酚化合物)等多酚化合物。
於本發明中，就獲得儲存穩定性與硬化性之平衡性優異之樹脂組合物之觀點而言，作為酚樹脂，較佳為使用數量平均分子量為750～1200者。
關於(E)成分相對於(C-1)成分、(C-2)成分或(C-3)成分之酚樹脂之使用量，相對於作為(C-1)成分、(C-2)成分及(C-3)成分之改性胺之合計100質量份，較佳為10～150質量份，更佳為20～60質量份。若酚樹脂之含量為10質量份以上，則樹脂組合物之硬化性變得更良好，故而較佳，若為150質量份以下，則所獲得之硬化物之物性變得更良好，故而較佳。
作為上述胺系潛在性硬化劑，可使用市售品。作為胺系潛在性硬化劑之市售品，可列舉：Adeka Hardener EH-3636S(ADEKA股份有限公司製；雙氰胺型潛在性硬化劑)、Adeka Hardener EH-4351S(ADEKA股份有限公司製；雙氰胺型潛在性硬化劑)、Adeka Hardener EH-5011S(ADEKA股份有限公司製；咪唑型潛在性硬化劑)、Adeka Hardener EH-5046S(ADEKA股份有限公司製；咪唑型潛在性硬化劑)、Adeka Hardener EH-4357S(ADEKA股份有限公司製；聚胺型潛在性硬化劑)、Adeka Hardener EH-5057P(ADEKA股份有限公司製；聚胺型潛在性硬化劑)、Adeka Hardener EH-5057PK(ADEKA股份有限公司製；聚胺型潛在性硬化劑)、Amicure PN-23(Ajinomoto Fine-Techno股份有限公司製；胺加成物系潛在性硬化劑)、Amicure PN-40(Ajinomoto Fine-Techno股份有限公司製；胺加成物系潛在性硬化劑)、Amicure VDH(Ajinomoto Fine-Techno股份有限公司製；醯肼系潛在性硬化劑)、FUJICURE FXR-1020(T＆K TOKA股份有限公司製；潛在性硬化劑)等。
本發明之樹脂組合物中之(C)胺系潛在性硬化劑之含量並無特別限定，相對於(A)氰酸酯樹脂及下述(D)環氧化合物之合計量100質量份，較佳為2～200質量份，更佳為5～100質量份。藉由將(C)胺系潛在性硬化劑之含量設為上述範圍，所獲得之樹脂組合物之黏度成為適當之範圍，故而較佳。
其次，對本發明之樹脂組合物中所含之(D)成分進行說明。作為(D)成分之環氧樹脂(但，腰果酚化合物之聚縮水甘油醚除外)只要係分子中具有至少2個環氧基者，則可無特別限制地使用，且其分子結構或分子量等並無特別限制。
作為上述環氧樹脂，例如可列舉：單核多酚化合物之聚縮水甘油醚化合物、多核多酚化合物之聚縮水甘油醚化合物、多元醇化合物之聚縮水甘油醚化合物、脂肪族多元酸之縮水甘油酯化合物、芳香族多元酸之縮水甘油酯化合物、脂環族多元酸之縮水甘油酯化合物、甲基丙烯酸縮水甘油酯之均聚物或共聚物、具有縮水甘油基胺基之環氧化合物、環狀烯烴化合物之環氧化物、環氧化共軛二烯聚合物、雜環化合物及茀型環氧樹脂。該等環氧樹脂可利用末端異氰酸酯之預聚物進行內部交聯，或亦可利用多價活性氫化合物(多酚、聚胺、含羰基之化合物、多磷酸酯等)進行高分子量化。於本發明之樹脂組合物中，環氧樹脂可單獨使用一種，亦可併用兩種以上。
作為上述單核多酚化合物，可列舉：對苯二酚、間苯二酚、兒茶酚及間苯三酚等。
作為上述多核多酚化合物，可列舉：二羥基萘、聯苯酚、亞甲基雙酚(雙酚F)、亞甲基雙(鄰甲酚)、亞乙基雙酚、亞異丙基雙酚(雙酚A)、亞異丙基雙(鄰甲酚)、四溴雙酚A、1,3-雙(4-羥基異丙苯基苯)、1,4-雙(4-羥基異丙苯基苯)、1,1,3-三(4-羥基苯基)丁烷、1,1,2,2-四(4-羥基苯基)乙烷、硫代雙酚、磺基雙酚、氧基雙酚、苯酚酚醛清漆、鄰甲酚酚醛清漆、乙基苯酚酚醛清漆、丁基苯酚酚醛清漆、辛基苯酚酚醛清漆、間苯二酚酚醛清漆及萜酚等。
作為上述多元醇化合物，可列舉：乙二醇、丙二醇、丁二醇、己二醇、聚乙二醇、聚丙二醇、硫甘醇、二環戊二烯二甲醇、2,2-雙(4-羥基環己基)丙烷(氫化雙酚A)、甘油、三羥甲基丙烷、季戊四醇、山梨糖醇、及雙酚A-環氧烷加成物等。
作為上述脂環族多元酸，例如可列舉：順丁烯二酸、反丁烯二酸、伊康酸、琥珀酸、戊二酸、辛二酸、己二酸、壬二酸、癸二酸、二聚酸及三聚酸。
作為上述芳香族多元酸，例如可列舉：鄰苯二甲酸、間苯二甲酸、對苯二甲酸、偏苯三甲酸、1,3,5-苯三甲酸及均苯四甲酸。
作為上述脂環族多元酸，例如可列舉：四氫鄰苯二甲酸及內亞甲基四氫鄰苯二甲酸等。
作為上述具有縮水甘油基胺基之環氧化合物，例如可列舉：N,N-二縮水甘油基苯胺、雙(4-(N-甲基-N-縮水甘油基胺基)苯基)甲烷、二縮水甘油基鄰甲苯胺、N,N-雙(2,3-環氧丙基)-4-(2,3-環氧丙氧基)-2-甲基苯胺、N,N-雙(2,3-環氧丙基)-4-(2,3-環氧丙氧基)苯胺及N,N,N',N'-四(2,3-環氧丙基)-4,4-二胺基二苯甲烷等。
作為上述環狀烯烴化合物，例如可列舉：乙烯基環己烯二環氧化物、環戊二烯二環氧化物、3,4-環氧環己烷羧酸3,4-環氧環己基甲酯、6-甲基環己烷羧酸3,4-環氧-6-甲基環己基甲酯及己二酸雙(3,4-環氧-6-甲基環己基甲基)酯等。
作為上述環氧化共軛二烯聚合物，例如可列舉：環氧化聚丁二烯及環氧化苯乙烯-丁二烯共聚物等。
作為上述雜環環氧化合物，例如可列舉異氰尿酸三縮水甘油酯等。
作為上述茀型環氧樹脂，例如可列舉下述式(3)所表示之環氧化合物。於本發明之樹脂組合物中，就可更進一步降低所獲得之硬化物之彈性模數之方面而言，作為環氧樹脂，較佳為使用茀型環氧樹脂，更佳為使用下述式(3)所表示之環氧化合物。作為式(3)所表示之茀型環氧樹脂之市售品，例如可列舉OGSOL EG-280(Osaka Gas Chemicals公司製造)。
[化7]
式中，n1
及n2
分別獨立地表示1～50之數，
X1
及X2
分別獨立地表示碳數1～4之伸烷基，
R7
、R8
、R9
及R10
分別獨立地表示氫原子、鹵素原子或碳數1～4之烷基。
作為上述式(3)中之R7
、R8
、R9
及R10
所表示之鹵素原子，可列舉：氯、溴、碘等。
作為上述式(3)中之R7
、R8
、R9
及R10
所表示之碳數1～4之烷基，可列舉與式(2)中之R1
及R2
所表示之碳數1～4之烷基相同者。
上述式(3)中之X1
及X2
所表示之碳數1～4之伸烷基可為直鏈狀，亦可為支鏈狀。作為直鏈狀之伸烷基，可列舉自甲基、乙基、正丙基及正丁基等直鏈狀之烷基之末端的碳原子去除1個氫原子所得之二價基。作為支鏈狀之伸烷基，例如可列舉自異丙基、異丁基、第二丁基、第三丁基等支鏈狀之伸烷基去除1個氫原子所得之二價基。
本發明之樹脂組合物中之(D)成分之上述環氧樹脂之含量並無特別限定，相對於上述氰酸酯樹脂100質量份，較佳為10～1000質量份，由於可獲得優異之硬化物性，故而更佳為200～800質量份。
於本發明中，可與上述潛在性硬化劑一同視需要併用公知之硬化促進劑。作為該等硬化促進劑之具體例，可例示：三苯基膦等膦類；四苯基溴化鏻等鏻鹽；2-甲基咪唑、2-苯基咪唑、2-乙基-4-甲基咪唑、2-十一烷基咪唑、1-氰乙基-2-甲基咪唑等咪唑類；作為上述咪唑類與偏苯三甲酸、異三聚氰酸、硼等之鹽之咪唑鹽類；苄基二甲基胺、2,4,6-三(二甲基胺基甲基)苯酚等胺類；氯化三甲基銨等四級銨鹽類；3-(對氯苯基)-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、異佛爾酮二異氰酸酯-二甲基脲、甲苯二異氰酸酯-二甲基脲等脲類；及三氟化硼與胺類或醚化合物等之錯合物等。該等硬化促進劑可單獨使用，亦可併用兩種以上。本發明之一液型氰酸酯-環氧複合樹脂組合物中之環氧樹脂硬化促進劑之含量並無特別限制，可根據一液型氰酸酯-環氧複合樹脂組合物之用途而適當設定。
於本發明之樹脂組合物中，視需要可含有各種添加劑。作為上述添加劑，可列舉：單烷基縮水甘油醚等反應性稀釋劑；鄰苯二甲酸二辛酯、鄰苯二甲酸二丁酯、苄醇、煤焦油等非反應性之稀釋劑(塑化劑)；熔融二氧化矽、結晶二氧化矽等二氧化矽；氫氧化鎂、氫氧化鋁、鉬酸鋅、碳酸鈣、碳酸矽、矽酸鈣、鈦酸鉀、氧化鈹、氧化鋯、鋯英石、鎂橄欖石、塊滑石、尖晶石、富鋁紅柱石、氧化鈦等粉體、或將該等球形化而成之顆粒、及玻璃纖維、紙漿纖維、合成纖維、陶瓷纖維等填充劑；玻璃布、芳族聚醯胺布、碳纖維等補強材料；顏料；γ-胺基丙基三乙氧基矽烷、N-β-(胺基乙基)-γ-胺基丙基三乙氧基矽烷、N-β-(胺基乙基)-N'-β-(胺基乙基)-γ-胺基丙基三乙氧基矽烷、γ-苯胺基丙基三乙氧基矽烷、γ-縮水甘油氧基丙基三乙氧基矽烷、β-(3,4-環氧環己基)乙基三乙氧基矽烷、乙烯基三乙氧基矽烷、N-β-(N-乙烯基苄基胺基乙基)-γ-胺基丙基三乙氧基矽烷、γ-甲基丙烯醯氧基丙基三甲氧基矽烷、γ-氯丙基三甲氧基矽烷、γ-巰基丙基三甲氧基矽烷等矽烷偶合劑；堪地里拉蠟、巴西棕櫚蠟、木蠟、蟲蠟、蜂蠟、羊毛脂、鯨蠟、褐煤蠟、石油蠟、脂肪族蠟、脂肪族酯、脂肪族醚、芳香族酯、芳香族醚等潤滑劑；增黏劑；觸變劑；抗氧化劑；光穩定劑；紫外線吸收劑；消泡劑；防銹劑；膠體二氧化矽、膠體氧化鋁等常用之添加劑。於本發明中，亦可進而併用二甲苯樹脂、石油樹脂等黏著性之樹脂類。
本發明之樹脂組合物可用於各種塗料、各種接著劑、各種成形材料。由於所獲得之硬化物為低彈性，故可適宜地用作要求耐衝擊性之材料或接著劑。
實施例
以下基於實施例詳細地說明本發明。然而，本發明並不受該等實施例任何限定。
製造例1(胺系潛在性硬化劑之合成)
將JEFFAMINE D230(聚醚聚胺、Huntsman公司製造)230 g加入至燒瓶中並加熱至60℃。繼而將Adeka Resin EP-4901E(環氧當量為170之雙酚F型環氧樹脂、ADEKA股份有限公司製造)190 g以系統內溫度保持為100～110℃之方式逐次少量添加至燒瓶中。於添加Adeka Resin EP-4901E後，使反應系統升溫至140℃，進行1.5小時反應而獲得改性胺。
相對於所獲得之改性胺100 g添加MP-800K(軟化點100℃之酚樹脂、旭有機材股份有限公司製造)50 g，於180～190℃、30～40 Torr下歷時1小時進行去溶劑，獲得改性胺與酚樹脂之混合物CE。
[實施例1-3及比較例1-3]
於常溫下混合下述[表1]所示之原料而製造樹脂組合物。混合使用行星式混合機。對所獲得之樹脂組合物之硬化物進行下述試驗。其評價結果示於下述[表1]。表1中之符號表示下述成分。又，表1中之原料之含量為質量份。於100℃下加熱所獲得之實施例1～3之樹脂組合物，結果迅速硬化。
A：雙酚型氰酸酯樹脂(Lonza公司製造、商品名：Lecy)
B-1：腰果酚單縮水甘油醚(Cardolite公司製造、商品名：NC-513)
B-2：C12～13烷基單縮水甘油醚(ADEKA股份有限公司製造、商品名：ED-502)
B-3：對第三丁基苯基單縮水甘油醚(ADEKA股份有限公司製造、商品名：ED-509E)
CE：製造例1中所獲得之改性胺與酚樹脂之混合物
D-1：茀型環氧樹脂(Osaka Gas Chemicals公司製造、商品名：OGSOL EG-280)
D-2：二環戊二烯型環氧樹脂(ADEKA股份有限公司製造、商品名：EP-4088L)
F：3-縮水甘油氧基丙基三乙氧基矽烷(矽烷偶合劑；商品名KBM-403、Shin-Etsu Silicones製造)
＜RSA試驗＞
使用動態黏彈性測定裝置RSA G2(TA Instruments Japan股份有限公司)，測定損失彈性模數(E'')及儲存模數(E')。測定範圍設為-50℃～200℃，測定條件設為頻率1 Hz、升溫速度10℃/min、樣品寬4 mm、夾頭間距離20 mm。表1中表示25℃下之儲存模數(E')。又，根據所測定之損失彈性模數(E'')及儲存模數(E')，根據tanδ(tanδ＝損失彈性模數(E'')/儲存模數(E'))之峰值溫度求出玻璃轉移溫度(Tg)。將結果示於表1。
[表1]
| 實施例 | 比較例 | ||||||
| 1 | 2 | 3 | 1 | 2 | 3 | ||
| 成分 | A | 40 | 40 | 20 | 40 | 40 | 40 |
| B-1 | 20 | 30 | 10 | ||||
| B-2 | 10 | 20 | |||||
| B-3 | 20 | ||||||
| CE | 100 | 100 | 100 | 100 | 100 | 100 | |
| D-1 | 80 | 60 | 90 | 100 | |||
| D-2 | 80 | 80 | |||||
| F | 2 | 2 | 2 | 2 | 2 | 2 | |
| 評價結果 | 玻璃轉移溫度Tg(℃) | 49 | 47 | 43 | 112 | 98 | 61 |
| 儲存模數(GPa) | 0.9 | 0.7 | 0.4 | 2.1 | 2.0 | 1.7 |
由表1表明，實施例1～3之樹脂組合物係玻璃轉移溫度及儲存模數(E')低於比較例1～3之樹脂組合物者。根據該結果表明，本發明之樹脂組合物能夠迅速硬化，且可獲得彈性較低之硬化物。
Claims (15)
- 一種樹脂組合物，其含有(A)氰酸酯樹脂、(B)腰果酚化合物或其縮水甘油醚、(C)胺系潛在性硬化劑及(D)環氧樹脂(但，腰果酚化合物之聚縮水甘油醚除外)。
- 如請求項1之樹脂組合物，其中上述氰酸酯樹脂係選自由下述式(1)所表示之化合物、及下述式(2)所表示之化合物、及該等化合物之預聚物所組成之群中之至少1種， NC-O-A1 -Y1 -A2 -O-CN (1) 式中，Y1 表示未經取代或經氟取代之二價烴基、-O-、-S-、或單鍵， A1 及A2 分別獨立地表示未經取代或經1～4個烷基取代之伸苯基；式中，m表示1以上之整數， Y2 表示硫原子、未經取代或經氟取代之二價烴基，複數個Y2 可相同亦可不同， R1 及R2 分別獨立地表示氫原子或碳數1～4之烷基。
- 如請求項2之樹脂組合物，其中上述式(1)中之Y1 及上述式(2)中之Y2 包含選自由下述式(Y-1)～(Y-10)所組成之群中之基，式中，n表示4～12之整數， R3 、R4 、R5 及R6 分別獨立地表示氫原子或者未經取代或經氟取代之甲基， *表示鍵結鍵。
- 如請求項1之樹脂組合物，其中上述(B)成分為腰果酚化合物、或其單縮水甘油醚。
- 如請求項1之樹脂組合物，其中上述(C)成分係具有活性氫之胺系潛在性硬化劑。
- 如請求項5之樹脂組合物，其中上述具有活性氫之胺系潛在性硬化劑為改性胺。
- 如請求項1之樹脂組合物，其中上述(C)成分係選自由下述(C-1)～(C-3)所組成之群中之至少1種， (C-1)：使具有1個以上活性氫之胺化合物與環氧化合物反應而成之改性胺； (C-2)：使具有1個以上活性氫之胺化合物與異氰酸酯化合物反應而成之改性胺； (C-3)：使具有1個以上活性氫之胺化合物、環氧化合物、及異氰酸酯化合物反應而成之改性胺。
- 如請求項7之樹脂組合物，其中作為上述(C)成分之胺系潛在性硬化劑為(C-1)， 上述具有1個以上活性氫之胺化合物為聚醚聚胺， 上述環氧化合物為多核多酚化合物之聚縮水甘油醚化合物。
- 如請求項7之樹脂組合物，其進而含有酚樹脂。
- 如請求項9之樹脂組合物，其相對於(C-1)、(C-2)及(C-3)之合計100質量份含有酚樹脂10～150質量份。
- 如請求項1之樹脂組合物，其中上述(B)成分之含量相對於上述(A)成分100質量份為10～1000質量份。
- 如請求項1之樹脂組合物，其中作為上述(C)成分之胺系潛在性硬化劑之含量相對於上述(A)氰酸酯樹脂及上述(D)環氧樹脂之合計量100質量份為2～200質量份。
- 如請求項1之樹脂組合物，其中上述(D)成分之含量相對於(A)成分100質量份為10～10000質量份。
- 一種接著劑，其包含如請求項1之樹脂組合物。
- 一種如請求項1之樹脂組合物之用途，其係用作接著劑。
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