JPS629249B2 - - Google Patents
Info
- Publication number
- JPS629249B2 JPS629249B2 JP15917079A JP15917079A JPS629249B2 JP S629249 B2 JPS629249 B2 JP S629249B2 JP 15917079 A JP15917079 A JP 15917079A JP 15917079 A JP15917079 A JP 15917079A JP S629249 B2 JPS629249 B2 JP S629249B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- general formula
- epoxy
- bis
- resin composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 imide compound Chemical class 0.000 claims description 18
- 239000004593 Epoxy Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000011342 resin composition Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000000962 organic group Chemical group 0.000 claims description 7
- 229920001187 thermosetting polymer Polymers 0.000 claims description 5
- 150000004985 diamines Chemical class 0.000 claims description 2
- 238000001723 curing Methods 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000005452 bending Methods 0.000 description 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 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 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000012778 molding material Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- YKNMIGJJXKBHJE-UHFFFAOYSA-N (3-aminophenyl)-(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC(N)=C1 YKNMIGJJXKBHJE-UHFFFAOYSA-N 0.000 description 1
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 description 1
- YTCGLFCOUJIOQH-UHFFFAOYSA-N 1,3,4-oxadiazole-2,5-diamine Chemical compound NC1=NN=C(N)O1 YTCGLFCOUJIOQH-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- BCMLMVXTJIMQTK-UHFFFAOYSA-N 2-[(4-phenoxyphenyl)sulfinylmethyl]thiirane Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1S(=O)CC1CS1 BCMLMVXTJIMQTK-UHFFFAOYSA-N 0.000 description 1
- HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical compound C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical group C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- AGULWIQIYWWFBJ-UHFFFAOYSA-N 3,4-dichlorofuran-2,5-dione Chemical compound ClC1=C(Cl)C(=O)OC1=O AGULWIQIYWWFBJ-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- IELKYPBJKLDRRX-UHFFFAOYSA-N 3-[(3-aminophenyl)-diethylsilyl]aniline Chemical compound C=1C=CC(N)=CC=1[Si](CC)(CC)C1=CC=CC(N)=C1 IELKYPBJKLDRRX-UHFFFAOYSA-N 0.000 description 1
- WNXAHYZTHTXSLW-UHFFFAOYSA-N 3-[(3-aminophenyl)diazenyl]aniline Chemical compound NC1=CC=CC(N=NC=2C=C(N)C=CC=2)=C1 WNXAHYZTHTXSLW-UHFFFAOYSA-N 0.000 description 1
- ZRJAHFLFCRNNMR-UHFFFAOYSA-N 3-amino-2-(4-aminophenyl)benzoic acid Chemical compound C1=CC(N)=CC=C1C1=C(N)C=CC=C1C(O)=O ZRJAHFLFCRNNMR-UHFFFAOYSA-N 0.000 description 1
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- KQIKKETXZQDHGE-FOCLMDBBSA-N 4,4'-diaminoazobenzene Chemical compound C1=CC(N)=CC=C1\N=N\C1=CC=C(N)C=C1 KQIKKETXZQDHGE-FOCLMDBBSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- KTZLSMUPEJXXBO-UHFFFAOYSA-N 4-[(4-aminophenyl)-phenylphosphoryl]aniline Chemical compound C1=CC(N)=CC=C1P(=O)(C=1C=CC(N)=CC=1)C1=CC=CC=C1 KTZLSMUPEJXXBO-UHFFFAOYSA-N 0.000 description 1
- HSBOCPVKJMBWTF-UHFFFAOYSA-N 4-[1-(4-aminophenyl)ethyl]aniline Chemical compound C=1C=C(N)C=CC=1C(C)C1=CC=C(N)C=C1 HSBOCPVKJMBWTF-UHFFFAOYSA-N 0.000 description 1
- BEKFRNOZJSYWKZ-UHFFFAOYSA-N 4-[2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(N)C=C1 BEKFRNOZJSYWKZ-UHFFFAOYSA-N 0.000 description 1
- ZYEDGEXYGKWJPB-UHFFFAOYSA-N 4-[2-(4-aminophenyl)propan-2-yl]aniline Chemical compound C=1C=C(N)C=CC=1C(C)(C)C1=CC=C(N)C=C1 ZYEDGEXYGKWJPB-UHFFFAOYSA-N 0.000 description 1
- HVMHLMJYHBAOPL-UHFFFAOYSA-N 4-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)propan-2-yl]-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2OC2CC1C(C)(C)C1CC2OC2CC1 HVMHLMJYHBAOPL-UHFFFAOYSA-N 0.000 description 1
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 1
- KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical compound C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- ADAHGVUHKDNLEB-UHFFFAOYSA-N Bis(2,3-epoxycyclopentyl)ether Chemical compound C1CC2OC2C1OC1CCC2OC21 ADAHGVUHKDNLEB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 1
- HNQHUWHQMJTWRA-UHFFFAOYSA-N NC1=CC=C(C=C1)C(C[PH2]=O)C1=CC=C(C=C1)N Chemical compound NC1=CC=C(C=C1)C(C[PH2]=O)C1=CC=C(C=C1)N HNQHUWHQMJTWRA-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- GLROGUSVUGSGPO-UHFFFAOYSA-N bis(3-methyl-7-oxabicyclo[4.1.0]heptan-4-yl) hexanedioate Chemical compound C1C2OC2CC(C)C1OC(=O)CCCCC(=O)OC1CC2OC2CC1C GLROGUSVUGSGPO-UHFFFAOYSA-N 0.000 description 1
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000002648 laminated material Substances 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
- Organic Insulating Materials (AREA)
Description
近年、エポキシ樹脂は、電気機器、電子部品な
どの分野に於いて、絶縁材料、コート材料、封止
材料として益々、その応用面の拡大がなされ、そ
の重要性も増している。
それに伴ないその性能に対する要求も厳しくな
つており、特に、エポキシ樹脂硬化物の熱的安定
性、機械的強度、電気的特性、硬化特性に関する
改良が、成形材料、積層材料、含浸ワニス、プリ
プレグなど、ほとんどあらゆる分野で望まれてい
る。
しかしながら、既存の硬化エポキシ樹脂の熱的
安定性については、通常のビスフエノール型エポ
キシ樹脂と、従来公知の硬化剤を組合せたもので
は、その熱変形温度が常温硬化型ポリアミド類を
用いた場合、40〜50℃、ポリアミン類を用いた場
合、50〜60℃、芳香族ポリアミン類を用いた場
合、70〜80℃であり、加熱硬化型芳香族ポリアミ
ンを用いた場合、100〜120℃であり、また、高い
熱変形温度を得るために、機械的強度とりわけ曲
げ強さ、衝撃強度を犠牲にするという弊害を生ず
る。熱安定性も常温硬化型ポリアミンを用いた場
合、100〜150℃、加熱硬化型ポリアミンを用いた
場合、150〜200℃が限度とされ、長時間に亘つて
かかる温度に曝されると熱劣化により、強度の低
下をきたし、好ましくない。
また、硬化特性の面に於いても、常温での安定
性と、150〜200℃での速硬化性を両立することは
むずかしく、安定な成形加工性を付与すること
は、従来のアミン系硬化剤では至難の技であつ
た。
一方、カルボン酸無水物を硬化剤として用いた
場合には、硬化物の熱安定性の向上、機械的強度
の向上はある程度可能であるが、アミン系硬化剤
の場合と同様に、常温での安定性と、高温での速
硬化性を両立することが難かしいこと、カルボン
酸無水物が吸湿性が大きいことから耐湿性が劣る
問題がある。
本発明は、このような状況に鑑みてなされたも
ので、その要点は、(A)エポキシ化合物および(B)一
般式〔〕
〔式中、R1はエチレン性不飽和基、R2は
In recent years, epoxy resins have been increasingly used as insulating materials, coating materials, and sealing materials in fields such as electrical equipment and electronic components, and their importance has been increasing. Along with this, the requirements for the performance of cured epoxy resins have also become stricter, and improvements in the thermal stability, mechanical strength, electrical properties, and curing properties of cured epoxy resins are particularly important for molding materials, laminated materials, impregnated varnishes, prepregs, etc. , is desired in almost every field. However, regarding the thermal stability of existing cured epoxy resins, the heat distortion temperature of ordinary bisphenol-type epoxy resins combined with conventionally known curing agents is lower than that when room-temperature curing polyamides are used. 40-50℃, 50-60℃ when polyamines are used, 70-80℃ when aromatic polyamines are used, and 100-120℃ when heat-curable aromatic polyamines are used. Moreover, in order to obtain a high heat distortion temperature, mechanical strength, especially bending strength and impact strength, are sacrificed. Thermal stability is also limited to 100 to 150°C when using room-temperature curing polyamines, and 150 to 200°C when using heat-curing polyamines, which can lead to thermal deterioration if exposed to such temperatures for a long time. This causes a decrease in strength, which is undesirable. In addition, in terms of curing properties, it is difficult to achieve both stability at room temperature and fast curing at 150 to 200℃, and it is difficult to achieve stable moldability using conventional amine-based curing methods. It was an extremely difficult technique with drugs. On the other hand, when carboxylic acid anhydride is used as a curing agent, it is possible to improve the thermal stability and mechanical strength of the cured product to some extent, but as with amine curing agents, it is possible to improve the thermal stability and mechanical strength of the cured product to some extent. There are problems in that it is difficult to achieve both stability and rapid curing at high temperatures, and that the carboxylic acid anhydride has a high hygroscopicity, resulting in poor moisture resistance. The present invention was made in view of this situation, and its main points are (A) an epoxy compound and (B) a general formula [] [In the formula, R 1 is an ethylenically unsaturated group, R 2 is
【式】（ｙはＨ、CH3、C2H5、Cl、Br またはOCH3を示す。）および[Formula] (y represents H, CH 3 , C 2 H 5 , Cl, Br or OCH 3. ) and
【式】（ｚ
はＨまたはCH3を示す。）
式中、ｍ＋ｎが平均で10以下である。〕で示さ
れるイミド系化合物と、
一般式〔〕
H2N−Ａ−NH2 〔〕
〔式中、Ａは30個以下の炭素原子の２価の有機
基〕で表わされるジアミンとを反応することによ
り得られるプレポリマを含むことを特徴とする熱
硬化樹脂組成物である。
本発明において、
一般式〔〕
〔式中、R1はエチレン性不飽和基、R2は
[Formula] (z represents H or CH 3 ) In the formula, m+n is 10 or less on average. ] and a diamine represented by the general formula [] H 2 N-A-NH 2 [] [wherein A is a divalent organic group having 30 or less carbon atoms]. It is a thermosetting resin composition characterized by containing a prepolymer obtained by. In the present invention, general formula [] [In the formula, R 1 is an ethylenically unsaturated group, R 2 is
【式】（ｙはＨ、CH3、C2H5、Cl、Br またはOCH3を示す。）および[Formula] (y represents H, CH 3 , C 2 H 5 , Cl, Br or OCH 3. ) and
【式】（ｚ
はＨまたはCH3を示す。）
式中、ｍ＋ｎが平均で10以下である。〕で示さ
れるイミド系化合物は、
一般式(1)
〔式中、R1は２ないし24個の炭素原子をもつ２価
有機基〕で表わされるエチレン性不飽和ジカルボ
ン酸無水物と、一般式(2)
〔式中、R2は[Formula] (z represents H or CH 3 ) In the formula, m+n is 10 or less on average. ] The imide compound represented by the general formula (1) [In the formula, R 1 is a divalent organic group having 2 to 24 carbon atoms] and an ethylenically unsaturated dicarboxylic acid anhydride represented by the general formula (2) [In the formula, R 2 is
【式】（R3は−H9−CH3、
−C2H5、−Cl、−Br、−OCH3を表わす）または、
[Formula] (R 3 represents -H 9 -CH 3 , -C 2 H 5 , -Cl, -Br, -OCH 3 ) or,
【式】（R4は−Ｈまたは−CH3を表わす）
を表わす〕で表わされるカルボン酸無水物と、一
般式(3)
〔式中、R1、R1′、R1″は−CH2−、−CH2OCH2
−、−CH2NH−、−CH2NHCH2−の内の同じ１種
または、異なつた種類〕で表わされる、軟化点
200℃以下のアニリン〜ホルムアルデヒド樹脂を
反応させることにより得られる。
本発明の一般式(1)で表わされるイミド系化合物
の赤外線吸収スペクトルは、1710cm-1と1780cm-1
にイミド結合のＣ＝０に基づく特性吸収を有す
る。
本発明において、一般式(1)
〔式中、R1は２ないし24個の炭素原子をもつ２価
の有機基〕で表わされるエチレン性不飽和ジカル
ボン酸無水物としては、例えば無水マレイン酸、
無水シトラコン酸、無水イタコン酸、無水ジクロ
ルマレイン酸あるいはこれらの化合物と、シクロ
ジエンとのデイールスアイダ付加物などの少なく
とも１種が用いられる。
また、本発明において、一般式(2)
〔式中、R2は[Formula] (R 4 represents -H or -CH 3 ) ] and the general formula (3) [In the formula, R 1 , R 1 ′, R 1 ″ are −CH 2 −, −CH 2 OCH 2
−, −CH 2 NH−, −CH 2 NHCH 2 − or different types]
Obtained by reacting aniline to formaldehyde resin at 200°C or lower. The infrared absorption spectrum of the imide compound represented by the general formula (1) of the present invention is 1710 cm -1 and 1780 cm -1
It has a characteristic absorption based on C=0 of imide bond. In the present invention, general formula (1) Examples of the ethylenically unsaturated dicarboxylic acid anhydride represented by [wherein R 1 is a divalent organic group having 2 to 24 carbon atoms] include maleic anhydride,
At least one of citraconic anhydride, itaconic anhydride, dichloromaleic anhydride, or a Diels-Aida adduct of these compounds with cyclodiene is used. In addition, in the present invention, general formula (2) [In the formula, R 2 is
【式】（R3は−Ｈ、−
CH3、−C2H5、−Cl、−Br、−OCH3を表わす）また
は、[Formula] (R 3 represents -H, -CH 3 , -C 2 H 5 , -Cl, -Br, -OCH 3 ) or,
【式】（R4は−Ｈまたは−CH3を表わ
す）を表わす〕で表わされるカルボン酸無水物と
しては、テトラヒドロフタル酸無水物、メチルテ
トラヒドロフタル酸無水物、エンドメチレンテト
ラヒドロフタル酸無水物などの少なくとも１種が
用いられる。
また、本発明において、一般式(3)
〔式中、R1、R1′、R1″は−CH2−、−CH2OCH2
−、−CH2NH−、−CH2NHCH2−の内の同じ１種
または、異なつた１種類〕で表わされるアニリン
〜ホルムアルデヒド樹脂は、例えばフランス特許
第1430997号、1481935号、1533696号による方法
で製造されるものであり、特に、アニリン〜ホル
ムアルデヒド樹脂の軟化点が200℃以下のものが
有用である。
また、一般式〔〕
H2N−Ａ−NH2 〔〕
〔式中、Ａは30個以下の炭素原子の２価の有機
基〕で表わされるジアミン化合物としては、例え
ば、ｍ−フエニレンジアミン、ｐ−フエニレンジ
アミン、ベンジジン、３・3′−ジメチル−４・
4′−ジアミノビフエニル、３・3′−ジクロロベン
ジジン、３・3′−ジメトキシベンジジン、４・
4′−ジアミノジフエニルメタン、１・１−ビス
（４−アミノフエニル）エタン、２・２−ビス
（４−アミノフエニル）プロパン、２・２−ビス
（４−アミノフエニル）ヘキサフルオロプロパ
ン、２・２−ビス（４−アミノフエニル）−１・
３−ジクロロ−１・１・３・３−テトラフルオロ
プロパン、４・4′−ジアミノジフエニルエーテ
ル、４・4′−ジアミノジフエニルサルフアイド、
３・3′−ジアミノジフエニルサルフアイド、４・
4′−ジアミノジフエニルスルホオキシド、４・
4′−ジアミノジフエニルスルホン、３・3′−ジア
ミノジフエニルスルホン、３・3′−ジアミノジベ
ンゾフエノン、４・4′−ジアミノベンゾフエノ
ン、３・4′−ジアミノベンゾフエノン、Ｎ・Ｎ−
ビス（４−アミノフエニル）アニリン、Ｎ・Ｎ−
ビス（４−アミノフエニル）メチルアミン、Ｎ・
Ｎ−ビス（４−アミノフエニル）−ｎ−ブチルア
ミン、ｍ−アミノベンゾイル−ｐ−アミノアニリ
ド、４−アミノフエニル−３−アミノベンゾエー
ト、４・4′−ジアミノアゾベンゼン、３・3′−ジ
アミノアゾベンゼン、ビス（３−アミノフエニ
ル）ジエチルシラン、ビス（４−アミノフエニ
ル）フエニルホスフインオキシド、ビス（４−ア
ミノフエニル）エチルホスフインオキシド、１・
５−ジアミノナフタリン、２・６−ジアミノピリ
ジン、２・５−ジアミノ−１・３・４−オキサジ
アゾール、ｍ−キシリレンジアミン、ｐ−キシリ
レンジアミン、２・４−（ｐ−β−アミノ−ｔ−
ブチルフエニル）エーテル、ｐ−ビス−２−（２
−メチル−４−アミノペンチル）ベンゼン、ｐ−
ビス（１・１−ジメチル−５−アミノペンチル）
ベンゼン、などがあげられる。
前記、一般式〔〕
〔式中、R1はエチレン性不飽和基、R2は
Examples of the carboxylic acid anhydride represented by the formula (R 4 represents -H or -CH 3 ) include tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, endomethylenetetrahydrophthalic anhydride, etc. At least one of these is used. In addition, in the present invention, general formula (3) [In the formula, R 1 , R 1 ′, R 1 ″ are −CH 2 −, −CH 2 OCH 2
-, -CH 2 NH-, -CH 2 NHCH 2 -, the same one type or one different type)] can be produced by the method according to, for example, French Patent Nos. 1430997, 1481935, and 1533696. In particular, aniline to formaldehyde resins with a softening point of 200°C or lower are useful. Further, as the diamine compound represented by the general formula [] H 2 N-A-NH 2 [] [wherein A is a divalent organic group having 30 or less carbon atoms], for example, m-phenylenediamine , p-phenylenediamine, benzidine, 3,3'-dimethyl-4,
4'-diaminobiphenyl, 3,3'-dichlorobenzidine, 3,3'-dimethoxybenzidine, 4,
4'-diaminodiphenylmethane, 1,1-bis(4-aminophenyl)ethane, 2,2-bis(4-aminophenyl)propane, 2,2-bis(4-aminophenyl)hexafluoropropane, 2,2- Bis(4-aminophenyl)-1.
3-dichloro-1,1,3,3-tetrafluoropropane, 4,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl sulfide,
3.3'-diaminodiphenyl sulfide, 4.
4'-diaminodiphenyl sulfoxide, 4.
4'-diaminodiphenylsulfone, 3,3'-diaminodiphenylsulfone, 3,3'-diaminodibenzophenone, 4,4'-diaminobenzophenone, 3,4'-diaminobenzophenone, N. N-
Bis(4-aminophenyl)aniline, N・N-
Bis(4-aminophenyl)methylamine, N.
N-bis(4-aminophenyl)-n-butylamine, m-aminobenzoyl-p-aminoanilide, 4-aminophenyl-3-aminobenzoate, 4,4'-diaminoazobenzene, 3,3'-diaminoazobenzene, bis( 3-aminophenyl)diethylsilane, bis(4-aminophenyl)phenylphosphine oxide, bis(4-aminophenyl)ethylphosphine oxide, 1.
5-diaminonaphthalene, 2,6-diaminopyridine, 2,5-diamino-1,3,4-oxadiazole, m-xylylenediamine, p-xylylenediamine, 2,4-(p-β-amino -t-
butylphenyl) ether, p-bis-2-(2
-Methyl-4-aminopentyl)benzene, p-
Bis(1,1-dimethyl-5-aminopentyl)
Examples include benzene. Above, general formula [] [In the formula, R 1 is an ethylenically unsaturated group, R 2 is
【式】（ｙはＨ、CH3、C2H5、Cl、Br またはOCH3を示す。）および[Formula] (y represents H, CH 3 , C 2 H 5 , Cl, Br or OCH 3. ) and
【式】（ｚ
はＨまたはCH3を示す。）
式中、ｍ＋ｎが平均で10以下である。〕で示さ
れるイミド系化合物と、
一般式（）
H2N−Ｒ−NH2 （）
〔式中、Ａは30個以下の炭素原子の２価の有機
基〕で表わされるジアミン化合物からプレポリマ
を作る際の両者の配合割合は、重量部比で前者の
イミド系化合物１に対して、後者のジアミン化合
物を0.1〜10の範囲で配合すればよい。
また、その製造法については、特に限定するも
のではないが、両者を混合加熱して、溶融状態で
反応させることにより、プレポリマ並びに、イミ
ド系化合物〔〕と、ジアミン化合物〔〕の割
合によつては硬化物が得られる。
次に本発明において多官能エポキシ化合物
（Ｙ）としては、例えばビスフエノールＡのジグ
リシジルエーテル、ブタジエンジエポキサイド、
３・４−エポキシシクロヘキシルメチル−（３・
４−エポキシ）シクロヘキサンカルボキシレー
ト、ビニルシクロヘキサンジオキシド、４・4′−
ジ（１・２−エポキシエチル）ジフエニルエーテ
ル、４・4′−（１・２−エポキシエチル）ビフエ
ニル、２・２−ビス（３・４−エポキシシクロヘ
キシル）プロパン、レゾルシンのグリシジルエー
テル、フロログルシンのジグリシジルエーテル、
メチルフロログリシンのジグリシジエーテル、ビ
ス−（２・３−エポキシシクロペンチル）エーテ
ル、２−（３・４−エポキシ）シクロヘキサン−
５・５−スピロ（３・４−エポキシ）−シクロヘ
キサン−ｍ−ジオキサン、ビス−（３・４−エポ
キシ−６−メチルシクロヘキシル）アジペート、
Ｎ・N′−ｍ−フエニレンビス（４・５−エポキ
シ−１・２−シクロヘキサン）ジカルボキシイミ
ドなどの２官能のエポキシ化合物、パラアミノフ
エノールのトリグリシジルエーテル、ポリアリル
グリシジルエーテル、１・３・５−トリ（１・２
−エポキシエチル）ベンゼン、２・2′・４・4′−
テトラグリシドキシベンゾフエノン、テトラグリ
シドキシテトラフエニルエタン、フエノールホル
ムアルデヒドノボラツクのボリグリシジルエーテ
ル、グリセリンのトリグリシジルエーテル、トリ
メチロールプロパンのトリグリシジルエーテルな
ど３官能以上のエポキシ化合物が用いられる。
前記一般式〔〕
〔式中、R1はエチレン性不飽和基、R2は
[Formula] (z represents H or CH 3 ) In the formula, m+n is 10 or less on average. ] and a diamine compound represented by the general formula () H 2 NR-NH 2 () [wherein A is a divalent organic group having 30 or less carbon atoms]. The mixing ratio of the two during production may be such that the latter diamine compound is blended in a range of 0.1 to 10 parts by weight to 1 part by weight of the former imide compound. The manufacturing method is not particularly limited, but by mixing and heating the two and reacting in a molten state, the prepolymer and the ratio of the imide compound [] and the diamine compound [] can be adjusted. A cured product is obtained. Next, in the present invention, examples of the polyfunctional epoxy compound (Y) include diglycidyl ether of bisphenol A, butadiene diepoxide,
3,4-Epoxycyclohexylmethyl-(3,
4-epoxy) cyclohexane carboxylate, vinylcyclohexane dioxide, 4,4'-
Di(1,2-epoxyethyl) diphenyl ether, 4,4'-(1,2-epoxyethyl)biphenyl, 2,2-bis(3,4-epoxycyclohexyl)propane, glycidyl ether of resorcin, phloroglucin diglycidyl ether,
Diglycididether of methylphlologlycine, bis-(2,3-epoxycyclopentyl)ether, 2-(3,4-epoxy)cyclohexane-
5,5-spiro(3,4-epoxy)-cyclohexane-m-dioxane, bis-(3,4-epoxy-6-methylcyclohexyl)adipate,
Bifunctional epoxy compounds such as N・N'-m-phenylenebis(4,5-epoxy-1,2-cyclohexane)dicarboximide, triglycidyl ether of para-aminophenol, polyallyl glycidyl ether, 1,3,5- Tori (1・2
-Epoxyethyl)benzene, 2, 2', 4, 4'-
Tri- or higher functional epoxy compounds are used, such as tetraglycidoxybenzophenone, tetraglycidoxytetraphenylethane, polyglycidyl ether of phenol formaldehyde novolac, triglycidyl ether of glycerin, and triglycidyl ether of trimethylolpropane. The above general formula [] [In the formula, R 1 is an ethylenically unsaturated group, R 2 is
【式】（ｙはＨ、CH3、数C2H5、Cl、
BrまたはOCH3を示す。）および
[Formula] (y represents H, CH 3 , number C 2 H 5 , Cl, Br or OCH 3. ) and
【式】（ｚはＨまたはCH3を示す。）
式中、ｍ＋ｎが平均で10以下である。〕で示さ
れるイミド系化合物と、
一般式〔〕
H2N−Ａ−NH2 〔〕
〔式中、Ａは30個以下の炭素原子の２価の有機
基〕で表わされるジアミン化合物から作られるプ
リポリマ（Ｘ）と、前記多官能エポキシ化合物
（Ｙ）の配合割合は、重量部比で、前者１に対し
て、後者0.1〜10の範囲で用いれば、本発明の効
果である、熱安定性のすぐれた樹脂組成物を得
る。
また、本発明の樹脂組成物の硬化方法について
は、特に限定するものではないが、通常、50−
200℃、で１〜60分程度加熱することにより、目
的とする硬化物を得ることができる。
また、本発明の樹脂組成物には、硬化反応を促
進させる触媒を添加することもできる。
用いる触媒としては、エポキシレジンの硬化反
応を促進する効果のある、従来公知の化合物なら
何んでも使用することができる。
例えば成形材料としての用途を考えると、ジル
コン、シリカ、溶融石英ガラス、ガラス、アルミ
ナ、炭酸カルシウム、マグネサイト、石コウ、亜
鉛華、チタン白、鉛化合物、クレー、カオリン、
タルク、珪砂、ホイスカー、カーボニルアイア
ン、フエライト、二硫化モリブデン、黒鉛、カー
ボンブラツク、アスベスト、ウオラストナイトな
どの無機質充填材料、脂肪酸、ワツクス類などの
離型剤、エポキシシラン、ビニルシラン、ボラン
系化合物、アルキルチタネート系化合物などのカ
ツプリング剤を使用できる。また必要に応じて、
公知の難燃化剤、あるいは可撓化剤を添加するこ
ともできる。
次に実施例を記して説明する。
実施例 １〜８
アニリン〜ホルムアルデヒド縮合樹脂と、テト
ラヒドロフタル酸無水物THPA、無水マレイン酸
MAを、表１に示した割合で反応させて、イミド
系化合物〜を得た。[Formula] (z represents H or CH 3 ) In the formula, m+n is 10 or less on average. ] and a diamine compound represented by the general formula [] H 2 N-A-NH 2 [] [wherein A is a divalent organic group with 30 or less carbon atoms] If the blending ratio of the prepolymer (X) and the polyfunctional epoxy compound (Y) is in the range of 1 to 10 for the former in the range of 0.1 to 10 for the latter, thermal stability, which is the effect of the present invention, can be improved. An excellent resin composition is obtained. Further, the method of curing the resin composition of the present invention is not particularly limited, but is usually 50-
By heating at 200°C for about 1 to 60 minutes, the desired cured product can be obtained. Moreover, a catalyst that promotes the curing reaction can also be added to the resin composition of the present invention. As the catalyst to be used, any conventionally known compound having the effect of accelerating the curing reaction of epoxy resin can be used. For example, considering its use as a molding material, zircon, silica, fused silica glass, glass, alumina, calcium carbonate, magnesite, gypsum, zinc white, titanium white, lead compounds, clay, kaolin,
Inorganic fillers such as talc, silica sand, whiskers, carbonyl iron, ferrite, molybdenum disulfide, graphite, carbon black, asbestos, and wollastonite, fatty acids, mold release agents such as waxes, epoxy silane, vinyl silane, borane compounds, Coupling agents such as alkyl titanate compounds can be used. Also, if necessary,
Known flame retardants or flexibilizers may also be added. Next, examples will be described and explained. Examples 1 to 8 Aniline-formaldehyde condensation resin, tetrahydrophthalic anhydride THPA, maleic anhydride
MA was reacted in the proportions shown in Table 1 to obtain imide compounds.
【表】
次いで、上記イミド系化合物〜と、４・
4′−ジアミノジフエニルメタン、４・4′−ジアミ
ノジフエニルエーテルのそれぞれと表２に示す所
定配合量で100〜150℃、15分間加熱反応して、プ
レポリマを得た。
このプレポリマ、エポキシ化合物、触媒を表２
の所定配合量に配合し、計８種類の配合物を作つ
た。そして、これらに、それぞれ、石英ガラス粉
70重量％、ステアリン酸カルシウム２重量部、カ
ツプリング剤として、エポキシシランKBM403
（信越化学製）１重量部を加え、混練したのち、
180℃、10分間加熱硬化して、目的の硬化物を得
た。
これらの硬化物のガラス転移点と、高温（180
℃）に於ける曲げ強さ、200℃、30日放置後の曲
げ強さの保持率を測定した。この結果を表２に示
す。[Table] Next, the above imide compounds ~ and 4.
A prepolymer was obtained by heating and reacting with each of 4'-diaminodiphenyl methane and 4,4'-diaminodiphenyl ether in the predetermined amounts shown in Table 2 at 100 to 150°C for 15 minutes. Table 2 shows this prepolymer, epoxy compound, and catalyst.
A total of 8 types of formulations were made by blending them in predetermined amounts. And each of these, quartz glass powder
70% by weight, 2 parts by weight of calcium stearate, epoxy silane KBM403 as a coupling agent
After adding 1 part by weight (manufactured by Shin-Etsu Chemical) and kneading,
The desired cured product was obtained by heating and curing at 180°C for 10 minutes. The glass transition point of these cured products and the high temperature (180
The bending strength at 200°C and the retention rate of bending strength after being left at 200°C for 30 days were measured. The results are shown in Table 2.
【表】【table】
Claims (1)
【式】（ｙはＨ、CH3、C2H5、Cl、Br またはOH3を示す。）および【式】（ｚは ＨまたはCH3を示す。）から選ばれるものであ
る。式中、ｍ＋ｎが平均で10以下である。〕で示
されるイミド系化合物と、 一般式〔〕 H2N−Ａ−NH2 〔〕 〔式中、Ａは30個以下の炭素原子の２価の有機
基〕で示されるジアミンとの反応により得られる
プレポリマを含むことを特徴とする熱硬化性樹脂
組成物。 ２ 特許請求の範囲第１項記載のイミド系化合物
式〔〕中のｍが１〜５、ｎが１〜５であること
を特徴とする熱硬化性樹脂組成物。 ３ 特許請求の範囲第１項記載のイミド系化合物
式〔〕中のR1が−CH＝CH−であることを特
徴とする熱硬化性樹脂組成物。 ４ (A)エポキシ化合物および(C)一般式（） 〔式中、R1はエチレン性不飽和基、R2は
【式】（ｙはＨ、CH3、C2H5、Cl、Br またはOCH3を示す。）および【式】（ｚ はＨまたはCH3を示す。） 式中、ｍ＋ｎが平均で10以下である。〕で示さ
れるイミド系化合物と、一般式〔〕との反応に
より得られるプレポリマを含むことを特徴とする
熱硬化性樹脂組成物。[Claims] 1 (A) Epoxy compound and (B) General formula [] [In the formula, R 1 is an ethylenically unsaturated group, R 2 is [Formula] (y represents H, CH 3 , C 2 H 5 , Cl, Br or OH 3 ) and [Formula] (z is H or CH 3 ). In the formula, m+n is 10 or less on average. ] and a diamine represented by the general formula [] H 2 N-A-NH 2 [] [where A is a divalent organic group with 30 or less carbon atoms]. A thermosetting resin composition comprising the obtained prepolymer. 2. A thermosetting resin composition, characterized in that m in the imide compound formula [] according to claim 1 is 1 to 5, and n is 1 to 5. 3. A thermosetting resin composition, wherein R 1 in the imide compound formula [ ] according to claim 1 is -CH=CH-. 4 (A) Epoxy compound and (C) general formula () [In the formula, R 1 is an ethylenically unsaturated group, R 2 is [Formula] (y represents H, CH 3 , C 2 H 5 , Cl, Br or OCH 3 ) and [Formula] (z is H or CH3 .) In the formula, m+n is 10 or less on average. ] A thermosetting resin composition comprising a prepolymer obtained by reacting an imide compound represented by the formula [ ] with the general formula [ ].
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15917079A JPS5682815A (en) | 1979-12-10 | 1979-12-10 | Thermosetting resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15917079A JPS5682815A (en) | 1979-12-10 | 1979-12-10 | Thermosetting resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5682815A JPS5682815A (en) | 1981-07-06 |
| JPS629249B2 true JPS629249B2 (en) | 1987-02-27 |
Family
ID=15687804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15917079A Granted JPS5682815A (en) | 1979-12-10 | 1979-12-10 | Thermosetting resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5682815A (en) |
-
1979
- 1979-12-10 JP JP15917079A patent/JPS5682815A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5682815A (en) | 1981-07-06 |
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