JPH02215825A - Epoxy resin composition - Google Patents
Epoxy resin compositionInfo
- Publication number
- JPH02215825A JPH02215825A JP3893789A JP3893789A JPH02215825A JP H02215825 A JPH02215825 A JP H02215825A JP 3893789 A JP3893789 A JP 3893789A JP 3893789 A JP3893789 A JP 3893789A JP H02215825 A JPH02215825 A JP H02215825A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- anhydride
- branched alkyl
- curing agent
- 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.)
- Pending
Links
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 40
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 40
- 239000000203 mixture Substances 0.000 title claims description 17
- 229940014800 succinic anhydride Drugs 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 abstract description 11
- 238000002156 mixing Methods 0.000 abstract description 6
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract description 4
- 230000007774 longterm Effects 0.000 abstract description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract description 2
- 239000000654 additive Substances 0.000 abstract description 2
- 239000003963 antioxidant agent Substances 0.000 abstract description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003063 flame retardant Substances 0.000 abstract description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004014 plasticizer Substances 0.000 abstract description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 abstract 1
- 230000003078 antioxidant effect Effects 0.000 abstract 1
- 235000006708 antioxidants Nutrition 0.000 abstract 1
- 238000013329 compounding Methods 0.000 abstract 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- -1 alkenyl succinic anhydride Chemical compound 0.000 description 14
- 150000008065 acid anhydrides Chemical class 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 4
- 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 4
- 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 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LLPKQRMDOFYSGZ-UHFFFAOYSA-N 2,5-dimethyl-1h-imidazole Chemical compound CC1=CN=C(C)N1 LLPKQRMDOFYSGZ-UHFFFAOYSA-N 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 2
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-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
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 239000011810 insulating material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 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 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- 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 1
- OQZDJLFNMXRJHZ-UHFFFAOYSA-N 1-benzyl-2-ethylimidazole Chemical compound CCC1=NC=CN1CC1=CC=CC=C1 OQZDJLFNMXRJHZ-UHFFFAOYSA-N 0.000 description 1
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- PZYAFUQTVNDJQU-UHFFFAOYSA-N 2-phenylhexadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCC(C(O)=O)C1=CC=CC=C1 PZYAFUQTVNDJQU-UHFFFAOYSA-N 0.000 description 1
- UIDDPPKZYZTEGS-UHFFFAOYSA-N 3-(2-ethyl-4-methylimidazol-1-yl)propanenitrile Chemical compound CCC1=NC(C)=CN1CCC#N UIDDPPKZYZTEGS-UHFFFAOYSA-N 0.000 description 1
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-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
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- FJTUUPVRIANHEX-UHFFFAOYSA-N butan-1-ol;phosphoric acid Chemical compound CCCCO.OP(O)(O)=O FJTUUPVRIANHEX-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 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
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- JFOJYGMDZRCSPA-UHFFFAOYSA-J octadecanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O JFOJYGMDZRCSPA-UHFFFAOYSA-J 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000009864 tensile test Methods 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical class C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明はエポキシ樹脂組成物に関し、更に詳しくは可撓
性に優れ、かつ長期の使用においても耐熱安定性が良好
なエポキシ樹脂組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an epoxy resin composition, and more particularly to an epoxy resin composition that has excellent flexibility and good heat resistance stability even during long-term use.
［従来の技術］
一般に、エポキシ樹脂は、電気特性、機械的性質、耐薬
品性等に優れることから、電気絶縁分野、土木、接着、
塗料分野に使用されて来た。中でも、硬化剤として酸無
水物を使用したエポキシ樹脂組成物は電気特性に優れる
ことから、電気絶縁材料として多用されている。しかし
ながら、これらの電気絶縁材料は、硬化時の収縮や熱衝
撃等による歪みにより注型物にクラックが発生したり、
注型部品を損傷したりすることが欠点として指摘されて
きた。[Prior Art] Generally, epoxy resins have excellent electrical properties, mechanical properties, chemical resistance, etc., and are used in the electrical insulation field, civil engineering, adhesives,
It has been used in the paint field. Among them, epoxy resin compositions using acid anhydrides as curing agents are often used as electrical insulating materials because of their excellent electrical properties. However, these electrical insulating materials may cause cracks in the cast product due to shrinkage during curing or distortion due to thermal shock, etc.
Damage to cast parts has been pointed out as a drawback.
斯かる欠点を解決する手段の一つに、硬化剤としてアル
ケニル無水コハク酸を使用することにより可撓性を付与
する方法が知られている（例えば、Ｐｏｌｙｍｅｒ、
Ｅｎｇ、 Ｓｃｉ、、１３．（５）、３５７．（１９７
３） ）。One known method for solving these drawbacks is to impart flexibility by using alkenyl succinic anhydride as a hardening agent (for example, Polymer,
Eng, Sci., 13. (5), 357. (197
3) ).
しかしながら、当該エポキシ樹脂組成物から得られる硬
化物は熱安定性が悪く、硬化物の可撓性、機械特性等が
経時的に損われ、必ずしも満足すべきものではなかった
。However, the cured products obtained from the epoxy resin compositions have poor thermal stability, and the flexibility, mechanical properties, etc. of the cured products deteriorate over time, and are not necessarily satisfactory.
［発明が解決しようとする課題］
本発明者らは、前記欠点を解決すべく鋭意検討の結果、
特定の置換基を有する無水コハク酸により硬化してなる
エポキシ樹脂組成物が可撓性に優れ、かつ耐熱安定性に
も優れることを見い出し、この知見に基いて本発明を完
成するに至った。[Problems to be Solved by the Invention] As a result of intensive studies to solve the above-mentioned drawbacks, the present inventors have found that
The inventors discovered that an epoxy resin composition cured with succinic anhydride having a specific substituent has excellent flexibility and excellent heat resistance stability, and based on this knowledge, the present invention was completed.
即ち、本発明は、可撓性に優れ、長期の耐熱安定性の良
好な新規なエポキシ樹脂組成物を提供することを目的と
する。That is, an object of the present invention is to provide a novel epoxy resin composition that is excellent in flexibility and has good long-term heat resistance stability.
［課題を解決するための手段］
本発明に係るエポキシ樹脂組成物は、エポキシ樹脂と分
岐状のアルキル基を有する無水コハク酸とを含有するこ
とを特徴とする。[Means for Solving the Problems] The epoxy resin composition according to the present invention is characterized by containing an epoxy resin and succinic anhydride having a branched alkyl group.
本発明において用いられるエポキシ樹脂は、１分子当り
１個以上のエポキシ基を有するものであればよく、例え
ば、ビスフェノールＡヤビスフェノールＦとエピハロヒ
ドリンとから合成されるグリシジルエーテル型エポキシ
樹脂、ノボラック型エポキシ樹脂、３，４−エポキシシ
クロへキシルメチル−３−４−一エボキシシクロヘキサ
ン力ルポキシレート等の脂環型エポキシ樹脂、ヘキサヒ
ドロフタル酸やテトラヒドロフタル酸のジグリシジルエ
ステル等のグリシジルエステル型エポキシ樹脂、水素化
ビスフェノールＡ、シクロヘキサンジメタツール等から
得られる脂環型エポキシ樹脂、ポリエステルポリオール
、ポリエーテルポリオールから得られるエポキシ樹脂、
ポリブタジェンやポリイソプレン等の不飽和重合体のエ
ポキシ化物等が挙げられる。更に、ビスフェノールＡの
代りに種々の多価フェノールを使用したり、フタル酸の
代りに伯の多塩基酸を用いることもできる。The epoxy resin used in the present invention may have one or more epoxy groups per molecule; for example, glycidyl ether type epoxy resin synthesized from bisphenol A Yabisphenol F and epihalohydrin, novolak type epoxy resin , alicyclic epoxy resins such as 3,4-epoxycyclohexylmethyl-3-4-mono-epoxycyclohexane lupoxylate, glycidyl ester type epoxy resins such as diglycidyl esters of hexahydrophthalic acid and tetrahydrophthalic acid, and hydrogenated bisphenols. A, alicyclic epoxy resin obtained from cyclohexane dimetatool, etc., epoxy resin obtained from polyester polyol, polyether polyol,
Examples include epoxidized products of unsaturated polymers such as polybutadiene and polyisoprene. Furthermore, various polyhydric phenols can be used in place of bisphenol A, and polybasic acids can be used in place of phthalic acid.
本発明で用いられる分岐状のアルキル基を有する無水コ
ハク酸は、例えばプロピレンやイソブチレンのオリゴマ
ーに無水マレイン酸を付加して得られるアルケニルコハ
ク酸を水素化反応することによって得られる。The succinic anhydride having a branched alkyl group used in the present invention can be obtained, for example, by hydrogenating alkenylsuccinic acid obtained by adding maleic anhydride to an oligomer of propylene or isobutylene.
このとき、分岐状のアルキル基の炭素数としては６〜１
８程度が好ましく、分岐状アルキル基における分岐の位
置又は分岐鎖の種類は、所定の効果が得られる限り、特
に限定されるものではない。At this time, the number of carbon atoms in the branched alkyl group is 6 to 1.
The number is preferably about 8, and the position of branching or type of branching in the branched alkyl group is not particularly limited as long as a predetermined effect can be obtained.
これらの分岐状アルキル無水コハク酸は、単独で又は２
種以上混合して適用される。These branched alkyl succinic anhydrides may be used alone or in combination with
It is applied by mixing more than one species.
エポキシ樹脂に対する分岐状アルキル無水コハク酸の混
合比率は、通常、カルボン酸無水物がエポキシ樹脂硬化
剤として用いられる範囲内であればいずれでもよく、例
えばエポキシ樹脂に対する当量比が０．５〜１．２程度
になるように配合することが好ましい。The mixing ratio of the branched alkyl succinic anhydride to the epoxy resin may be in any range as long as the carboxylic acid anhydride is normally used as an epoxy resin curing agent, for example, the equivalent ratio to the epoxy resin is 0.5 to 1. It is preferable to mix it so that it becomes about 2.
本発明に係るエポキシ樹脂組成物においては、必要に応
じて他の酸無水物系硬化剤を適宜併用することが出来る
。具体的には、通常、エポキシ樹脂硬化剤として用いら
れているものでおればよく、例えば無水フタル酸、無水
テトラヒドロフタル酸、無水へキサヒドロフタル酸、無
水メチルテトラヒドロフタル酸、無水メチルへキサヒド
ロフタル酸、無水３，６−ニンドメヂレンテトラヒドロ
フタル酸、無水ピロメリット酸、無水ドデセニルコハク
酸、無水ポリ（エチルオクタデカンニ酸）、無水ポリ（
フェニルヘキサデカンニ酸）、ドデセニル無水コハク酸
、無水ベンゾフェノンテトラカルボン酸、エチレングリ
コールビス（アンヒドロトリメリテート）、グリセロー
ルトリストリメリテーｌ〜無水物、無水ヘット酸、無水
テトラブロモフタル酸等が例示される。In the epoxy resin composition according to the present invention, other acid anhydride curing agents can be appropriately used in combination as necessary. Specifically, any curing agent that is normally used as an epoxy resin curing agent may be used, such as phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methyl hexahydrophthalic anhydride. Phthalic acid, 3,6-nindomedylenetetrahydrophthalic anhydride, pyromellitic anhydride, dodecenylsuccinic anhydride, poly(ethyl octadecanedioic acid) anhydride, poly(anhydride)
Examples include phenylhexadecanedioic acid), dodecenyl succinic anhydride, benzophenone tetracarboxylic anhydride, ethylene glycol bis(anhydrotrimellitate), glycerol tristrimeritate anhydride, hetyl anhydride, tetrabromophthalic anhydride, etc. Ru.
本発明に係る分岐状アルキル無水コハク酸と上記の汎用
酸無水物との配合比率は、所定の効果が得られる限り特
に限定されるものではないが、好ましくは酸無水物全量
に対する分岐状アルキル無水コハク酸の含有率が２０重
滑％以上、より好ましくは３０重量％以上である。２０
重量％より少ない配合比率では、エポキシ樹脂組成物に
対して所定の可撓性を付与することが困難である。The blending ratio of the branched alkyl succinic anhydride according to the present invention and the above-mentioned general-purpose acid anhydride is not particularly limited as long as a predetermined effect can be obtained, but preferably the branched alkyl succinic anhydride is The content of succinic acid is 20% by weight or more, more preferably 30% by weight or more. 20
If the blending ratio is less than % by weight, it is difficult to impart the desired flexibility to the epoxy resin composition.
本発明に係るエポキシ樹脂組成物は、常法に従って、５
０〜２５０℃程度、好ましくは７０〜１８０℃で加熱す
ることによって硬化し、所定の特性を有する硬化物を形
成する。The epoxy resin composition according to the present invention can be prepared by
It is cured by heating at about 0 to 250°C, preferably 70 to 180°C, to form a cured product having predetermined properties.
この場合、第三級アミン、イミダゾール類、金属エステ
ル系化合物及び燐系化合物等、公知の反応促進剤を用い
ることができる。In this case, known reaction accelerators such as tertiary amines, imidazoles, metal ester compounds, and phosphorus compounds can be used.
第三級アミンとしては、Ｎ、Ｎ−ジメチルシクロヘキシ
ルアミン、Ｎ、Ｎ−ジメチルアニリン、ジメチルベンジ
ルアミン、Ｎ、Ｎ−ジメチルラウリルアミン、ベンゾト
リアゾール等が例示される。Examples of the tertiary amine include N,N-dimethylcyclohexylamine, N,N-dimethylaniline, dimethylbenzylamine, N,N-dimethyllaurylamine, and benzotriazole.
イミダゾール類としては、１−シアノエチル−２−エチ
ル−４−メチルイミダゾール、１−シアンエチル−２−
メチルイミダゾール、１−ベンジル−２−エチルイミダ
ゾール、２−メチルイミダゾール、２−エチルイミダゾ
ール、２−フェニルイミダゾール、２，４−ジメチルイ
ミダゾール及びこれらのトリメリット酸、酢酸、ピバリ
ン酸等の塩等が例示される。As imidazoles, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-
Examples include methylimidazole, 1-benzyl-2-ethylimidazole, 2-methylimidazole, 2-ethylimidazole, 2-phenylimidazole, 2,4-dimethylimidazole, and salts thereof such as trimellitic acid, acetic acid, pivalic acid, etc. be done.
金属エステル系化合物としては、ジオクチル錫オキサイ
ド、ジブチル錫オキサイド、トリブチル錫オキサイド、
ジスタノキサン化合物、トリフェニル錫化合物、オクチ
ル酸錫、ステアリン酸錫等の錫系化合物や、オクチル酸
亜鉛等が例示される。Examples of metal ester compounds include dioctyltin oxide, dibutyltin oxide, tributyltin oxide,
Examples include tin-based compounds such as distanoxane compounds, triphenyltin compounds, tin octylate, and tin stearate, and zinc octylate.
更に、燐系化合物としては、トリフェニルホスファイト
、トリエチルホスファイト、ブチルアシッドホスフェー
ト、ジエチルホスフォネート、トリフェニルホスフィン
、テトラフェニルホスホニウムテトラフェニルボレート
等が例示される。Furthermore, examples of the phosphorus compound include triphenylphosphite, triethylphosphite, butyl acid phosphate, diethylphosphonate, triphenylphosphine, tetraphenylphosphonium tetraphenylborate, and the like.
これらの硬化促進剤は、単独で使用しても２種以上の化
合物を併用してもよく、通常、エポキシ樹脂１００重量
部に対して０．０１〜５重量部程度、好ましくは０．１
〜１重徨部添加される。These curing accelerators may be used alone or in combination of two or more kinds of compounds, and are usually about 0.01 to 5 parts by weight, preferably 0.1 parts by weight, based on 100 parts by weight of the epoxy resin.
~1 heavy weight is added.
その他の添加剤としては、例えば、シリカ、アルミナ、
アルミナ水和物、タルク、ケイ藻土、マイカ、アスベス
ト、炭酸カルシウム、＠酸バリウム、ガラスピーズ、ガ
ラス繊維等の無機質充填剤、酸化アンチモン、ハロゲン
化合物、リン化合物等の難燃剤、高級脂肪酸金属塩、エ
ステル系ワックス等の離型剤、酸化チタン、カーボンブ
ラック、フタロシアニン化合物等の顔料、シランカップ
リング剤、希釈剤、消泡剤、可塑剤、酸化防止剤等が掲
げられ、必要に応じて適宜配合することが出来る。Other additives include silica, alumina,
Inorganic fillers such as alumina hydrate, talc, diatomaceous earth, mica, asbestos, calcium carbonate, barium oxide, glass peas, and glass fibers, flame retardants such as antimony oxide, halogen compounds, and phosphorus compounds, higher fatty acid metal salts , mold release agents such as ester waxes, pigments such as titanium oxide, carbon black, and phthalocyanine compounds, silane coupling agents, diluents, antifoaming agents, plasticizers, antioxidants, etc., and may be added as appropriate as necessary. Can be mixed.
本発明に係るエポキシ樹脂組成物は、常法に従い、例え
ば、エクストルーダー、ニーダ−、ロール等を用いて混
練することにより調製され、自動車電装品の絶縁封止や
、リレー、スイッチ、コイル、トランス等の封止用組成
物として適用される。The epoxy resin composition according to the present invention is prepared by kneading according to a conventional method, for example, using an extruder, kneader, roll, etc., and is used for insulation sealing of automobile electrical components, relays, switches, coils, transformers, etc. It is applied as a sealing composition such as.
［実 施 例］ 以下に実施例を掲げ、本発明の詳細な説明する。[Example] The present invention will be described in detail below with reference to Examples.
エポキシ樹脂組成物を評価するに際して用いた特性の測
定方法を以下に示す。The method of measuring the properties used in evaluating the epoxy resin composition is shown below.
ガラス−、（Ｔｇ＞・・・示差熱分析による。Glass-, (Tg>...by differential thermal analysis.
■張腫瓜・・・ＡＳＴＭ Ｄ１７０８−８４に従い、
２５℃で測定する。■ Zhang Tuan...According to ASTM D1708-84,
Measure at 25°C.
ｍ・・・引張試験片を空気循環式のオーブン中で、１５
０℃、２４時間及び１００時間エージングを行なった後
、前記と同様に引張伸度を測定する。m...Tensile test piece was placed in an air circulation oven for 15 minutes.
After aging at 0° C. for 24 hours and 100 hours, the tensile elongation is measured in the same manner as above.
乞ヱ止亘二Ｉ皇墓遺・・・ＪＩＳ Ｋ−６９１１に従
って測定し、可撓性の尺度とした。Koji Wataru I Imperial Tomb Remains: Measured according to JIS K-6911 and used as a measure of flexibility.
実施例１
ビスフェノールＡジグリシジルエーテル（以下ｒＤＧＥ
ＢＡＪと略記する。商品名：エピコート８２８、シェル
化学■Ｉ）７０重量部、ポリプロピレン、グリコール（
分子量４００）（以下ｒＰＰＧ４００Ｊと略記する。商
品名：サンニツクスＰＰＧ４００、三洋化成工業■製）
３０重量部、分岐状の炭素数１２のアルキル基で置換さ
れた無水コハク酸６８．３重量部及びベンジルジメチル
アミン（以下ｒＢＤＭＡＪと略記する。）２．５重量部
を混合し、１２０℃、２時間の条件で硬化してエポキシ
樹脂硬化物を調製した。酸無水物とエポキシ樹脂の当量
比は０．７である。このもののＴｇ、耐熱安定性及び可
撓性を評価して１ｑられた結果を第１表に示す。Example 1 Bisphenol A diglycidyl ether (rDGE)
It is abbreviated as BAJ. Product name: Epicote 828, Shell Chemical I) 70 parts by weight, polypropylene, glycol (
molecular weight 400) (hereinafter abbreviated as rPPG400J.Product name: Sannix PPG400, manufactured by Sanyo Chemical Industries, Ltd.)
30 parts by weight, 68.3 parts by weight of succinic anhydride substituted with a branched alkyl group having 12 carbon atoms, and 2.5 parts by weight of benzyldimethylamine (hereinafter abbreviated as rBDMAJ) were mixed, and the mixture was heated at 120°C for 2 hours. A cured epoxy resin was prepared by curing under the conditions of a certain amount of time. The equivalent ratio of acid anhydride to epoxy resin is 0.7. Table 1 shows the results of evaluating the Tg, heat resistance stability and flexibility of this material.
実施例２〜４
分岐状アルキル無水コハク酸の種類を変えた以外は実施
例１と同様な方法でエポキシ樹脂硬化物を調製し、ＴＱ
、耐熱安定性、可撓性を測定した。Examples 2 to 4 Cured epoxy resins were prepared in the same manner as in Example 1 except that the type of branched alkyl succinic anhydride was changed, and the TQ
, heat stability, and flexibility were measured.
得られた結果を第１表に示す。The results obtained are shown in Table 1.
比較例１〜３
酸無水物系硬化剤を各種のアルケニル無水コハク酸に変
えた以外は実施例１と同様にしてエポキシ樹脂硬化物を
調製し、このもののＴｇ、耐熱安定性及び可撓性を評価
した。得られた結果を第１表に示す。Comparative Examples 1 to 3 Epoxy resin cured products were prepared in the same manner as in Example 1, except that the acid anhydride curing agent was changed to various alkenyl succinic anhydrides, and the Tg, heat resistance stability, and flexibility of this product were evaluated. evaluated. The results obtained are shown in Table 1.
比較例４
ＤＧＥＢＡ１００重量部に対し、メチルへキサヒドロ無
水フタル酸（以下ｒＭｅ−ＨＨＰＡＪと略記する。商品
名：ＭＨ−７００、新日本理化■製）８０重量部及びＢ
ＤＭＡ２．５重量部を混合し、実施例１と同様にしてエ
ポキシ樹脂硬化物を調製した。このもののＴｇ、耐熱安
定性及び可撓性について評価した結果を第１表に示す。Comparative Example 4 To 100 parts by weight of DGEBA, 80 parts by weight of methylhexahydrophthalic anhydride (hereinafter abbreviated as rMe-HHPAJ, trade name: MH-700, manufactured by Shin Nihon Rika ■) and B
A cured epoxy resin was prepared in the same manner as in Example 1 by mixing 2.5 parts by weight of DMA. Table 1 shows the results of evaluating the Tg, heat resistance stability, and flexibility of this product.
［発明の効果］
本−発明に係る酸無水物を硬化剤として適用することに
より、可撓性に優れ、かつ長期の耐熱安定性に優れたエ
ポキシ樹脂組成物を得ることができる。[Effects of the Invention] By applying the acid anhydride according to the present invention as a curing agent, an epoxy resin composition having excellent flexibility and long-term heat resistance stability can be obtained.
Claims (1)
ハク酸とを含有することを特徴とするエポキシ樹脂組成
物。1. An epoxy resin composition containing an epoxy resin and succinic anhydride having a branched alkyl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3893789A JPH02215825A (en) | 1989-02-17 | 1989-02-17 | Epoxy resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3893789A JPH02215825A (en) | 1989-02-17 | 1989-02-17 | Epoxy resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02215825A true JPH02215825A (en) | 1990-08-28 |
Family
ID=12539138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3893789A Pending JPH02215825A (en) | 1989-02-17 | 1989-02-17 | Epoxy resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02215825A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003068841A1 (en) * | 2002-02-15 | 2003-08-21 | Kyowa Hakko Chemical Co., Ltd. | Resin composition |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5592728A (en) * | 1979-01-08 | 1980-07-14 | Mitsubishi Petrochem Co Ltd | Epoxy resin composition |
| JPS62116623A (en) * | 1985-11-15 | 1987-05-28 | Nippon Zeon Co Ltd | Epoxy resin composition |
-
1989
- 1989-02-17 JP JP3893789A patent/JPH02215825A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5592728A (en) * | 1979-01-08 | 1980-07-14 | Mitsubishi Petrochem Co Ltd | Epoxy resin composition |
| JPS62116623A (en) * | 1985-11-15 | 1987-05-28 | Nippon Zeon Co Ltd | Epoxy resin composition |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003068841A1 (en) * | 2002-02-15 | 2003-08-21 | Kyowa Hakko Chemical Co., Ltd. | Resin composition |
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