JP6985273B2 - 包接化合物及びその製造方法並びにその用途 - Google Patents
包接化合物及びその製造方法並びにその用途 Download PDFInfo
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- JP6985273B2 JP6985273B2 JP2018531880A JP2018531880A JP6985273B2 JP 6985273 B2 JP6985273 B2 JP 6985273B2 JP 2018531880 A JP2018531880 A JP 2018531880A JP 2018531880 A JP2018531880 A JP 2018531880A JP 6985273 B2 JP6985273 B2 JP 6985273B2
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- alkyl
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- 150000001875 compounds Chemical class 0.000 title claims description 283
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- -1 fluorene compound Chemical class 0.000 claims description 124
- 239000000203 mixture Substances 0.000 claims description 71
- 125000003118 aryl group Chemical group 0.000 claims description 49
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 47
- 239000003795 chemical substances by application Substances 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 239000003822 epoxy resin Substances 0.000 claims description 43
- 229920000647 polyepoxide Polymers 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000001624 naphthyl group Chemical group 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
- 238000010438 heat treatment Methods 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000003367 polycyclic group Chemical group 0.000 claims description 13
- 125000002252 acyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 239000000470 constituent Substances 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 238000001723 curing Methods 0.000 description 82
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- 238000005259 measurement Methods 0.000 description 20
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 150000008065 acid anhydrides Chemical class 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 16
- 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 15
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 13
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- 150000002170 ethers Chemical class 0.000 description 12
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- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 11
- 125000003700 epoxy group Chemical group 0.000 description 11
- 238000004455 differential thermal analysis Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 229920003986 novolac Polymers 0.000 description 10
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- HKMTVMBEALTRRR-UHFFFAOYSA-N 1,2-benzofluorene Natural products C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 150000002220 fluorenes Chemical class 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000006467 substitution reaction Methods 0.000 description 9
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 229920000768 polyamine Polymers 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 229930185605 Bisphenol Natural products 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000005452 bending Methods 0.000 description 7
- 238000005266 casting Methods 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 7
- 125000005027 hydroxyaryl group Chemical group 0.000 description 7
- 229920001568 phenolic resin Polymers 0.000 description 7
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 7
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- 239000005062 Polybutadiene Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000004014 plasticizer Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- HPHCUWNVOLOGRP-UHFFFAOYSA-N 1-[9-(2-hydroxynaphthalen-1-yl)fluoren-9-yl]naphthalen-2-ol Chemical class C1=CC=C2C(C3(C4=CC=CC=C4C4=CC=CC=C43)C3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 HPHCUWNVOLOGRP-UHFFFAOYSA-N 0.000 description 5
- PTBCCLLVPOLXES-UHFFFAOYSA-N 2-[9-(2-hydroxyphenyl)fluoren-9-yl]phenol Chemical class OC1=CC=CC=C1C1(C=2C(=CC=CC=2)O)C2=CC=CC=C2C2=CC=CC=C21 PTBCCLLVPOLXES-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000000539 dimer Substances 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 5
- 238000004898 kneading Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- NUDSREQIJYWLRA-UHFFFAOYSA-N 4-[9-(4-hydroxy-3-methylphenyl)fluoren-9-yl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(O)=CC=2)=C1 NUDSREQIJYWLRA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 229920000459 Nitrile rubber Polymers 0.000 description 4
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical group N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 125000004018 acid anhydride group Chemical group 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 4
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000000806 elastomer Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 4
- 239000000347 magnesium hydroxide Substances 0.000 description 4
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 150000003003 phosphines Chemical class 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 4
- 229960001755 resorcinol Drugs 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 4
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 3
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 3
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 description 3
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 3
- DYOPVXMHYSXHNG-UHFFFAOYSA-N 6-[9-(6-hydroxynaphthalen-2-yl)fluoren-9-yl]naphthalen-2-ol Chemical compound C1=C(O)C=CC2=CC(C3(C4=CC=CC=C4C4=CC=CC=C43)C3=CC4=CC=C(C=C4C=C3)O)=CC=C21 DYOPVXMHYSXHNG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HAPOJKSPCGLOOD-UHFFFAOYSA-N Benzo[b]fluorene Chemical compound C1=CC=C2C=C3CC4=CC=CC=C4C3=CC2=C1 HAPOJKSPCGLOOD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- UUQQGGWZVKUCBD-UHFFFAOYSA-N [4-(hydroxymethyl)-2-phenyl-1h-imidazol-5-yl]methanol Chemical compound N1C(CO)=C(CO)N=C1C1=CC=CC=C1 UUQQGGWZVKUCBD-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000005263 alkylenediamine group Chemical group 0.000 description 3
- 125000003046 allene group Chemical group 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 239000006082 mold release agent Substances 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
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- 238000006116 polymerization reaction Methods 0.000 description 3
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- 239000003566 sealing material Substances 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229920002379 silicone rubber Polymers 0.000 description 3
- 239000004945 silicone rubber Substances 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 125000001302 tertiary amino group Chemical group 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- RUEBPOOTFCZRBC-UHFFFAOYSA-N (5-methyl-2-phenyl-1h-imidazol-4-yl)methanol Chemical compound OCC1=C(C)NC(C=2C=CC=CC=2)=N1 RUEBPOOTFCZRBC-UHFFFAOYSA-N 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- 125000006713 (C5-C10) cycloalkyl group Chemical group 0.000 description 2
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 description 2
- XZKLXPPYISZJCV-UHFFFAOYSA-N 1-benzyl-2-phenylimidazole Chemical compound C1=CN=C(C=2C=CC=CC=2)N1CC1=CC=CC=C1 XZKLXPPYISZJCV-UHFFFAOYSA-N 0.000 description 2
- IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical group C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
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- 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
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
-
- 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
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Description
包接化合物では、ホスト分子により形成された空間内にゲストとして小分子が取り込まれ、共有結合によらずゲストが安定に存在する。
本発明の包接化合物において、ホスト化合物は、式(1)で表される化合物を含んでいる。
本発明において、式(1)で表され、ホスト分子として用いられる代表的な化合物には、環Ar1及びAr2がベンゼン環である9,9−ビス(ヒドロキシアリール)フルオレン類が含まれる。このような化合物には、前記式(1)において、(a1)環Z1及びZ2がベンゼン環であり、n1及びn2が1である9,9−ビス(ヒドロキシフェニル)フルオレン類;(a2)環Z1及びZ2がナフタレン環であり、n1及びn2が1である9,9−ビス(ヒドロキシナフチル)フルオレン類;(a3)環Z1及びZ2がベンゼン環であり、n1及びn2が2以上である9,9−ビス(ポリヒドロキシフェニル)フルオレン類などが含まれる。
9,9−ビス(ヒドロキシフェニル)フルオレン類としては、R1及びR2が炭化水素基であり、m1及びm2が0又は1である化合物が好適に使用される。
上記9,9−ビス(ヒドロキシナフチル)フルオレン類には、上記例示の9,9−ビス(ヒドロキシフェニル)フルオレン類の環Z1及びZ2がナフタレン環である9,9−ビス(ヒドロキシナフチル)フルオレン類{例えば、9,9−ビス(2−ヒドロキシ−6−ナフチル)フルオレン、9,9−ビス[1−(5−ヒドロキシナフチル)]フルオレンなどの9,9−ビス(ヒドロキシナフチル)フルオレンなど}などが含まれる。
さらに、上記9,9−ビス(ポリヒドロキシフェニル)フルオレン類には、前記9,9−ビス(ヒドロキシフェニル)フルオレン類[9,9−ビス(モノヒドロキシフェニル)フルオレン類]に対応するフルオレン類、例えば、9,9−ビス(ジヒドロキシフェニル)フルオレン[9,9−ビス(3,4−ジヒドロキシフェニル)フルオレン(ビスカテコールフルオレン)など];9,9−ビス(3,4−ジヒドロキシ−5−メチルフェニル)フルオレン、9,9−ビス(3,4−ジヒドロキシ−6−メチルフェニル)フルオレンなどの9,9−ビス(アルキル−ジヒドロキシフェニル)フルオレン[例えば、9,9−ビス(C1−4アルキル−ジヒドロキシフェニル)フルオレンなど]などの9,9−ビス(ジ又はトリヒドロキシフェニル)フルオレン類が含まれる。
代表的な上記式(1)で表される化合物には、(b1)一方の環Ar1がベンゼン環であり、他方の環Ar2がナフタレン環であるベンゾフルオレン類、(b2)環Ar1およびAr2がナフタレン環であるジベンゾフルオレン類などが含まれる。
ベンゾフルオレン類には、例えば、11,11−ビス(ヒドロキシアリール)ベンゾ[a]フルオレン類,11,11−ビス(ヒドロキシアリール)ベンゾ[b]フルオレン類、7,7−ビス(ヒドロキシアリール)ベンゾ[c]フルオレン類が含まれる。
代表的なジベンゾフルオレン類には、12,12−ビス(ヒドロキシアリール)ジベンゾ[b,h]フルオレン類が含まれる。
本発明において、ゲスト分子として用いられる化合物は、環の構成原子として複数の窒素原子(例えば、塩基性窒素原子)を含む5又は6員複素環又はその縮合複素環を有する複素環化合物を含んでいる。複素環化合物は、脂肪族性複素環(非芳香族性複素環)又は芳香族性複素環のいずれであってもよい。複素環化合物において、環を形成する窒素原子(例えば、塩基性窒素原子)の数は、例えば、2〜5、好ましくは2〜4程度であってもよい。
本発明の包接化合物は、前記式(1)で表される化合物(ホスト化合物)と、前記複素環化合物(ゲスト化合物)とを、混合又は反応させることにより調製できる。なお、ホスト化合物及びゲスト化合物のうち少なくとも一方の成分が混合温度(例えば、常温又は30〜100℃程度)で液体である場合、液体である一方の成分に他方の成分を添加して混合してもよい。例えば、ゲスト化合物が液体である場合、ゲスト化合物に、ホスト化合物を添加し、必要に応じて混合(又は撹拌)し、ろ取などにより回収することにより生じた包接化合物を得ることができる。加熱下で混合又は撹拌する場合、冷却した後、回収することにより包接化合物を得ることができる。
本発明の包接化合物は、エポキシ樹脂の硬化剤として機能する複素環化合物を安定に包接するため、エポキシ樹脂と混合しても低温(常温若しくは貯蔵温度)では長時間に亘り安定である。一方、包接化合物は、加熱に伴って複素環化合物を放出するため、所定温度に加熱すると、エポキシ樹脂を迅速に硬化させることができる。また、本発明の包接化合物は、第一級アミノ基又は第二級アミノ基とともに第三級アミノ基を有しているためか、エポキシ樹脂の硬化剤として機能するとともに硬化促進剤として機能させることもできる。そのため、本発明の包接化合物は、(B)エポキシ樹脂(エポキシ化合物)を硬化させるための(A)硬化剤及び/又は硬化促進剤として有用である。さらに、(A)包接化合物(硬化剤及び/又は硬化促進剤)は、(B)エポキシ樹脂(エポキシ化合物)と組み合わせて硬化性組成物を調製するのに有用である。
[実施例1](BCF:2E4MZの包接化合物の合成)
9,9−ビス(4−ヒドロキシ−3−メチルフェニル)フルオレン(BCF、大阪ガスケミカル(株)製、3.78g,10mmol)の酢酸エチル(10mL)溶液に、70℃で、2−エチル−4−メチルイミダゾール(2E4MZ、四国化成工業(株)製、2.30g,21mmol)で加えた。1時間の撹拌の後、加熱を停止して室温まで冷却し、生成した固体をろ取、乾燥し、生成物を得た(白色固体、収量3.66g)。得られた包接化合物は、1H−NMRおよびTG−DTAにより包接比BCF:2E4MZ=1:1の包接化合物であることを確認した。
9,9−ビス(4−ヒドロキシ−3,5−ジメチルフェニル)フルオレン(BXF、大阪ガスケミカル(株)製、4.05g,10mmol)の酢酸エチル(15mL)懸濁液に、70℃で、2−エチル−4−メチルイミダゾール(2E4MZ、四国化成工業(株)製、2.26g,21mmol)で加える以外、実施例1と同様にして生成物を得た(白色固体、収量4.18g)。得られた包接化合物は、1H−NMRおよびTG−DTAにより包接比BXF:2E4MZ=1:1の包接化合物であることを確認した。
9,9−ビス(6−ヒドロキシナフタレン−2−イル)フルオレン(BNF、大阪ガスケミカル(株)製、907mg、2mmol)のメタノール(4mL)溶液に、60℃で、2−エチル−4−メチルイミダゾール(2E4MZ、四国化成工業(株)製、444mg,4mmol)で加えた。1時間の撹拌の後、冷却し、反応混合液を水(50mL)に加え、生成した固体をろ過し、乾燥し、生成物を得た(白色固体、収量712mg)。得られた包接化合物は、1H−NMRおよびTG−DTAにより包接比BNF:2E4MZ=1:1の包接化合物であることを確認した。
BCF(3.78g、10mmol)の酢酸エチル(15mL)の溶液に、70℃で、2−メチルイミダゾール(2MZ−H、四国化成工業(株)製、1.81g,22mmol)を加えた。5分間の加熱の後、冷却し、生成した固体をろ過し、乾燥し、生成物を得た(白色固体、収量3.00g)。1H−NMRおよびTG−DTAにより包接比BCF:2MZ−H=1:2の包接化合物であることを確認した。
BXF(4.07g,10mmol)の酢酸エチル(15mL)の溶液に、70℃で、2−メチルイミダゾール(2MZ−H、四国化成工業(株)製、1.81g,22mmol)を加えた。100分間の加熱の後、冷却し、生成した固体をろ過し、乾燥し、生成物を得た(白色固体、収量3.91g)。1H−NMRおよびTG−DTAにより包接比BXF:2MZ−H=1:1の包接化合物であることを確認した。
BCF(377mg、1mmol)の酢酸エチル(8mL)の溶液に、ジアザビシクロウンデセン(DBU、東京化成(株)製、344mg,2.3mmol)を加えた。DBUの漏出を防止しつつ容器中、100℃で加熱撹拌の後、冷却し、生成した固体をろ過し、乾燥し、生成物を得た(白色固体、収量660mg)。1H−NMRおよびTG−DTAにより包接比BCF:DBU=1:2の包接化合物であることを確認した。
[実施例7:硬化性組成物]
液状エポキシ樹脂100重量部(jER828、三菱化学(株)製)に、実施例1で得られた包接化合物(BCF:2E4MZ)13.3重量部(2E4MZとして3重量部)を加え、ホモジナイザー((株)日本精機製作所製、エースホモジナイザーAM−10)を用い、回転数15000rpmで10分撹拌し、硬化性組成物を調製した。
液状エポキシ樹脂100重量部(jER828、三菱化学(株)製)に3重量部の2E4MZを加え、実施例7と同様にして硬化性組成物を調製した。
JIS C 2161に準拠し、所定の温度に温められたステンレス板上に試料をおき、毎分60回の速度で円状にスパチュラでかきまぜ、試料がゲル状になり、試料がスパチュラに付着しなくなった点あるいは糸引きがなくなった点を終点とした。表2に示すように、実施例7の硬化性組成物は、比較例1と同等のゲル化時間を示した。
液状エポキシ樹脂100重量部(jER 828、三菱化学(株)製)と、実施例2〜3で得られた所定量の包接化合物(イミダゾールとして3重量部)とを用いて実施例7と同様にして硬化性組成物(実施例8及び実施例9の硬化組成物)を調製した。また、対照として比較例1の硬化性組成物を用いた。
前記硬化性組成物を収容する容器を氷水で冷却しながら混練後、25℃で20分間静置した後、組成物の一部をサンプリングし、E型粘度計(東機産業(株)製「TVE−22L」)を用いて、25℃で所定時間毎に粘度(mPa・s/25℃)を測定した。結果を表4に示す。
以下の手順に従い、硬化物試験片を作製した。
液状エポキシ樹脂(jER 828、三菱化学(株)製)100重量部、実施例1で得られた包接化合物(BCF:2E4MZ)10重量部を、らいかい機(石川式撹拌擂潰機18号、(株)石川工場製)を用いて、包接化合物をエポキシ樹脂に分散させたのち、真空脱泡して注型用セル[セロハン張りのアルミニウム板(3mm厚)2枚の間に、スペーサーとして直径Φ3mm又は4mmのシリコーンゴムを介在させてクリップで固定したセル]に注ぎ込み、熱風循環オーブン中で下記表5に記載の条件にて硬化させた。なお、スペーサーの直径は、試験片のサイズに応じて適宜変更した。
液状エポキシ樹脂(jER 828)100重量部及び2−エチル−4−メチルイミダゾール(2E4MZ)3重量部をスパチュラを用いてよく混合した。これを真空脱泡して注型用セルに注ぎ込み、熱風循環オーブン中で下記表5に記載の条件にて硬化させた。
液状エポキシ樹脂(jER 828)100重量部、実施例1で得られた包接化合物(BCF:2E4MZ)10重量部を、らいかい機(石川式撹拌擂潰機18号、(株)石川工場製)を用いて混練後、酸無水物系化合物(MH−700、新日本理化(株)製、酸無水物当量164g/eq.)86.3重量部を加えて、スパチュラで混合し、真空脱泡後、注型用セルに注ぎ込み、熱風循環オーブン中で下記表5に記載の条件にて硬化させた。なお、酸無水物系化合物は、エポキシ樹脂のエポキシ基1モルに対して、酸無水物系化合物の酸無水物基1モルの割合で配合した。
液状エポキシ樹脂(jER 828)100重量部、2−エチル−4−メチルイミダゾール(2E4MZ)3重量部及び酸無水物系化合物(MH−700)86.3重量部をスパチュラを用いてよく混合した。これを真空脱泡して注型用セルに注ぎ込み、熱風循環オーブン中で下記表5に記載の条件にて硬化させた。なお、酸無水物系化合物は、エポキシ樹脂のエポキシ基1モルに対して、酸無水物系化合物の酸無水物基1モルの割合で配合した。
フェノール系化合物(PSM−4261、群栄化学工業(株)製、フェノール樹脂、水酸基当量103g/eq.)54.2重量部及び実施例1で得られた包接化合物(BCF:2E4MZ)10重量部を二本ロール(6インチミキシングロールDY6−15、(株)ダイハン製)にて100℃で混練し、さらに、液状エポキシ樹脂(jER 828)100重量部を添加して約5分間混練を行った。ロールから取り出した後、100℃に加熱して、注型用セルに注ぎ込み、熱風循環オーブン中で下記表5に記載の条件にて硬化させた。なお、フェノール系化合物は、エポキシ樹脂のエポキシ基1モルに対して、フェノール系化合物の水酸基1モルの割合で配合した。
液状エポキシ樹脂(jER 828)100重量部及びフェノール系化合物(PSM−4261)54.2重量部を二本ロールにて90〜100℃で混練した。ロールから取り出した後、2−エチル−4−メチルイミダゾール(2E4MZ)3重量部を添加し、100℃のオーブンで加熱してスパチュラで混合したのち、注型用セルに注ぎ込み、熱風循環オーブン中で下記表5に記載の条件にて硬化させた。なお、フェノール系化合物は、エポキシ樹脂のエポキシ基1モルに対して、フェノール系化合物の水酸基1モルの割合で配合した。
試験片:約80mm×10mm×4.0mm
測定条件:試験速度 2mm/min;
支点間距離 64mm
試験温度 室温又は260℃
測定装置:万能材料試験機 5582型(インストロン社製)
なお、曲げ弾性率は初期直線部分の接線弾性率から算出した。
試験方法:空洞共振器接道法(ASTM D 2520に準拠)
試験片:80mm×1.5mm×1.5mm厚
測定条件:周波数 1GHz
試験環境 23±2℃、50±5%RH
測定数 n=2
測定装置:PNA−L ネットワークアナライザ N5230A(アジレント・テクノロジー(株)製)
空洞共振器 CP431((株)関東電子応用開発製)。
測定条件:測定温度 室温〜300℃
昇温速度 5℃/min
雰囲気 窒素気流中(50mL/min)
測定モード 圧縮モード(荷重 20mN)
測定装置:TMA 8310((株)リガク製)。
測定項目:E’、E”、tanδ
試験片:短冊 50mm×10mm×3mm
測定条件:測定温度 室温〜300℃
昇温速度 4.0℃/min
周波数 1Hz
雰囲気 窒素気流中(300mL/min)
測定モード 曲げモード
測定装置:EXSTAR DMS6100 ((株)日立ハイテクサイエンス製)。
試験片:約50mm×50mm×3.0mm
試験方法:試験片を下記条件で乾燥後、水中に浸漬し、浸漬後の試験片重量と、事前乾燥後の試験片重量との差を、事前乾燥後の試験片重量で除することにより算出した
測定条件:事前乾燥 50℃×24h
水中への浸漬 23℃×24h
測定数 n=3。
Claims (15)
- 下記式(1)で表される化合物をホスト化合物とし、環の構成原子として複数の窒素原子を含む5又は6員複素環又はその縮合複素環を有する化合物をゲスト化合物として含む包接化合物(A)であって;
下記(A1)又は(A2)である包接化合物。
(A1)前記包接化合物(A)のうち、下記式(I)で表されるフルオレン化合物と、下記式(II)で表されるイミダゾール化合物との包接化合物を除く包接化合物
mは0〜4の整数を示し、nは0〜4の整数を示し;
X2は、それぞれ同一又は異なってハロゲン原子、置換基を有していてもよいC1−6アルキル基、ヒドロキシル基、置換基を有していてもよいC1−6アルコキシ基、アミノ基、ニトロ基、又はシアノ基を示し;
pは0〜4の整数を示し、q0は0〜4の整数を示す)
RII〜RIVは、それぞれ同一又は異なって水素原子、ハロゲン原子、置換基を有していてもよいC1−6アルキル基、置換基を有していてもよいC6−10アリール基、ニトロ基、又はシアノ基を示す)
(A2)前記ホスト化合物が、前記式(1)において、Ar 1 及びAr 2 がベンゼン環であり;Z 1 及びZ 2 がベンゼン環であり;R 1 及びR 2 がアルキル基であり;m1及びm2が1である化合物であり、
前記ゲスト化合物が、2,4−ジアルキルイミダゾールである包接化合物 - 前記包接化合物(A1)におけるホスト化合物が、式(1)において、Ar1及びAr2が、同一又は異なって、ベンゼン環又はナフタレン環であり;Z1及びZ2が、同一又は異なって、ベンゼン環又はナフタレン環であり;R1及びR2が、同一又は異なって、アルキル基、シクロアルキル基、アリール基、アラルキル基、アルコキシ基、シクロアルコキシ基、アリールオキシ基、アラルキルオキシ基、アシル基、アルコキシカルボニル基、ハロゲン原子、ニトロ基、シアノ基又は置換アミノ基であり;R3及びR4が、同一又は異なって、アルキル基、シクロアルキル基、アリール基、アラルキル基、アルコキシ基、ハロゲン原子、ニトロ基、シアノ基又は置換アミノ基であり;n1及びn2が、同一又は異なって1〜3の整数であり;m1及びm2が、同一又は異なって0〜2の整数であり;p1及びp2が同一又は異なって0〜2の整数である請求項1記載の包接化合物。
- 前記包接化合物(A1)におけるホスト化合物が、式(1)において、Ar1及びAr2がベンゼン環であり;Z1及びZ2がベンゼン環又はナフタレン環であり;n1及びn2が1又は2であり;R1及びR2が、同一又は異なって、C1−4アルキル基又はC6−10アリール基であり、m1及びm2が0〜2の整数であり;p1及びp2が0である請求項1又は2記載の包接化合物。
- 前記包接化合物(A1)におけるホスト化合物が、式(1)において、R1及びR2がメチル基又はフェニル基であり、m1及びm2が1又は2である請求項1〜3のいずれかに記載の包接化合物。
- ホスト化合物1モルに対してゲスト化合物を0.5〜5モルの割合で含む請求項1〜6のいずれかに記載の包接化合物。
- 請求項1記載の式(1)で表される化合物と、環の構成原子として複数の窒素原子を含む5又は6員複素環又はその縮合複素環を有する化合物とを混合し、請求項1〜7のいずれかに記載の包接化合物を製造する方法。
- エポキシ樹脂を硬化させるための硬化剤又は硬化促進剤であって、請求項1〜7のいずれかに記載の包接化合物を含む硬化剤又は硬化促進剤。
- 請求項1〜7のいずれかに記載の包接化合物とエポキシ樹脂とを含む硬化性組成物。
- エポキシ樹脂が液状エポキシ樹脂である請求項10に記載の硬化性組成物。
- エポキシ樹脂100重量部に対して包接化合物を0.1〜25重量部の割合で含む請求項10又は11記載の硬化性組成物。
- 酸無水物系化合物をさらに含む請求項10〜12のいずれかに記載の硬化性組成物。
- 請求項10〜13のいずれかに記載の硬化性組成物が硬化した硬化物。
- 請求項10〜13のいずれかに記載の硬化性組成物を加熱して硬化させ、硬化物を製造する方法。
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