JPS62227920A - Heat-resistant epoxy resin composition - Google Patents
Heat-resistant epoxy resin compositionInfo
- Publication number
- JPS62227920A JPS62227920A JP7049186A JP7049186A JPS62227920A JP S62227920 A JPS62227920 A JP S62227920A JP 7049186 A JP7049186 A JP 7049186A JP 7049186 A JP7049186 A JP 7049186A JP S62227920 A JPS62227920 A JP S62227920A
- Authority
- JP
- Japan
- Prior art keywords
- polyamine
- epoxy resin
- resin composition
- epoxy
- heat
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 12
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 11
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 11
- 229920000768 polyamine Polymers 0.000 claims abstract description 28
- 239000004593 Epoxy Substances 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 abstract description 10
- 238000002156 mixing Methods 0.000 abstract description 5
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 19
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- -1 0-ethylaniline Chemical compound 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- 229920003319 Araldite® Polymers 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 241000283986 Lepus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000010425 asbestos Substances 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000005350 fused silica glass Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000002648 laminated material Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000012763 reinforcing filler Substances 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 229910052895 riebeckite Inorganic materials 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- YKOLZVXSPGIIBJ-UHFFFAOYSA-N 2-Isopropylaniline Chemical compound CC(C)C1=CC=CC=C1N YKOLZVXSPGIIBJ-UHFFFAOYSA-N 0.000 description 1
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-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
- OGIQUQKNJJTLSZ-UHFFFAOYSA-N 4-butylaniline Chemical compound CCCCC1=CC=C(N)C=C1 OGIQUQKNJJTLSZ-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 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 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 241000219122 Cucurbita Species 0.000 description 1
- 235000009852 Cucurbita pepo Nutrition 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 229910017852 NH2NH2 Inorganic materials 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 241001474791 Proboscis Species 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- AUNAPVYQLLNFOI-UHFFFAOYSA-L [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O Chemical compound [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O AUNAPVYQLLNFOI-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- IZALUMVGBVKPJD-UHFFFAOYSA-N benzene-1,3-dicarbaldehyde Chemical compound O=CC1=CC=CC(C=O)=C1 IZALUMVGBVKPJD-UHFFFAOYSA-N 0.000 description 1
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- CJOBVZJTOIVNNF-UHFFFAOYSA-N cadmium sulfide Chemical compound [Cd]=S CJOBVZJTOIVNNF-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000019241 carbon black Nutrition 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 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
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910002026 crystalline silica Inorganic materials 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 238000000617 electron capture negative ionisation mass spectrometry Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012850 fabricated material Substances 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000003733 fiber-reinforced composite Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 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 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- UCNNJGDEJXIUCC-UHFFFAOYSA-L hydroxy(oxo)iron;iron Chemical compound [Fe].O[Fe]=O.O[Fe]=O UCNNJGDEJXIUCC-UHFFFAOYSA-L 0.000 description 1
- 239000012784 inorganic fiber Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000011490 mineral wool Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- ILCQYORZHHFLNL-UHFFFAOYSA-N n-bromoaniline Chemical class BrNC1=CC=CC=C1 ILCQYORZHHFLNL-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 239000012945 sealing adhesive Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は高いガラス転位＠度を有し、高温下での機械的
特性の低下が少ない耐熱性エポキシ樹脂組成物に関する
ものである。このエポキシ樹脂組成物は、積層材料、繊
維強化複合材料、粉体塗料、封止材料および接着剤とし
て有用である。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a heat-resistant epoxy resin composition that has a high glass transition degree and exhibits little deterioration in mechanical properties at high temperatures. This epoxy resin composition is useful as a laminated material, fiber-reinforced composite material, powder coating, sealing material, and adhesive.
エポキシ樹脂の芳香族アミン硬化物は機械的特性に優れ
、強靭でバランスがとれており、膣気的陸質もよく、耐
薬品比も特に耐アルカリ性、耐溶剤比の優れたものが得
られる。これら芳香族アミンとして、メタフェニレンジ
アミン、ジアミノジフェニルメタンおよびジアミノジフ
ェニルスルホンがよく知られており、実際に吏用されて
いる。The aromatic amine cured product of epoxy resin has excellent mechanical properties, is strong and well-balanced, has good air quality, and has excellent chemical resistance, especially alkali resistance and solvent resistance. As these aromatic amines, metaphenylene diamine, diaminodiphenylmethane and diaminodiphenylsulfone are well known and are actually used.
しかしながら、メタフェニレンジアミンおよびジアミノ
ジフェニルメタンは毒性があり、かつそれらの硬化物の
耐熱性は低いという問題を有している。However, metaphenylene diamine and diaminodiphenylmethane are toxic, and their cured products have low heat resistance.
一方、ジアミノジフェニルスルホンの便化物は、＠熱性
が高くなるが、硬化が遅く、吸水率が大きい。まだ債最
品にした場合、ドリル加工性に帷があり、必ずしも議定
されるものではない。On the other hand, feces of diaminodiphenylsulfone has high thermal properties, but hardens slowly and has a high water absorption rate. However, if it is made into a bond, there is a limit to its drillability, and it is not necessarily something that can be determined.
〔間：１Ａ点を解決するための手段〕
本発明は、従来の芳香族ポリアミン硬化物の上記間須点
を改良するためになされたものであり、以下の組成物を
用いることにより特に耐熱性の優れた硬化′吻が得られ
る。[Means for solving the 1A point] The present invention was made to improve the above-mentioned problems of conventional aromatic polyamine cured products, and by using the following composition, the heat resistance An excellent cured proboscis is obtained.
即ち、大発明は、
（５）成分：一分子中に少なくとも２個のエポキシ基を
有するエポキシ化合物
（Ｂ）成分：下記−１股式（Ｉ）で示されるポリアミン
ＮＨ２ＮＨ２
〔式中、Ｘば水素原子、ハロゲン原子または炭素数１〜
４のアルキル基もしくはアルコキシ基である〕
上記囚および（Ｂ）成分が配合されていることを特徴と
する耐熱性エポキシ樹脂組成物を提供するものである。That is, the great invention is as follows: (5) Component: an epoxy compound having at least two epoxy groups in one molecule (B) component: a polyamine NH2NH2 represented by the following -1-pronged formula (I) [wherein X is hydrogen] Atom, halogen atom or carbon number 1~
The present invention provides a heat-resistant epoxy resin composition characterized by containing the above group and component (B).
（エポキシ化合物）
（４）成分の一分子中に少なくとも２個のエポキシ基を
有するエポキシ化合物としては、たとえば次のものが挙
げられる。(Epoxy Compound) Examples of the epoxy compound having at least two epoxy groups in one molecule of component (4) include the following.
（ｉ） ビスフェノールＡのジグリシジルエーテル；
その商品としては油化シェルエポキシ株式会社のエピコ
ート８２７、同８２８、同８３４、同８６４、同１００
１、同１００４、同１００７、同１０３１、テバ社のア
ラルダイトＧＹ２５０．同６０９９、ユニオンカーバイ
ド社のＥＲＬ２７７４、ダウケミカル社のＤＥＲ３３２
、同３３１、同６６１、（以上いずれも商品名）等。(i) diglycidyl ether of bisphenol A;
The products include Epicoat 827, 828, 834, 864, and 100 from Yuka Shell Epoxy Co., Ltd.
1, 1004, 1007, 1031, Teva Araldite GY250. 6099, Union Carbide's ERL2774, Dow Chemical's DER332
, 331, 661, (all of the above are product names), etc.
（１１）エポキシフェノールノボラック；その摺品とし
ては油化シェルエポキシ株式会社のエピコート１５２、
同１５４、ダウケミカル社のＤＥＮ４３８、同４４８、
チパ社のアラルダイトＥＰＮＩ１３８、同１１３９（以
上いずれも商品名）等。(11) Epoxyphenol novolak; examples of its printing products include Epicoat 152 manufactured by Yuka Shell Epoxy Co., Ltd.;
154, DOW Chemical Company's DEN438, 448,
Chipa's Araldite EPNI138, EPNI1139 (all of the above are product names), etc.
（１１リ エホキシクレゾールノポラック；その商品
としてはチパ社のアラルダイトＥＣＮＩ ２３５、同１
２７３、同１２８０（以上いずれも商品名）等。(11 riephoxycresol nopolac; its products include Chipa's Araldite ECNI 235, same 1
273, 1280 (all of the above are product names), etc.
その曲、ビスフェノールＦのジグリシジルエーテル、フ
タル管又はヘキサヒドルフタル俊トエビクロルヒドリン
から得られるエポキシ樹脂、バラハイドロオキシ安息香
酸とエピクロルヒドリンより得られるエポキシ樹脂、ト
ルイジンやアニリン等の芳δ挨アミンとエピクロルヒド
リンより得られるエボギン船（脂、ビニルシクロヘキセ
ンジオキシド、１．４−ブタンジオールジグリシジルエ
ーテル、ｌ、６−ヘキサンシオールジグリシジルエーテ
ル等があげられる。The song, diglycidyl ether of bisphenol F, epoxy resin obtained from phthalate or hexahydrofthalate shrimp chlorohydrin, epoxy resin obtained from rosehydroxybenzoic acid and epichlorohydrin, aromatic resins such as toluidine and aniline. Examples include epoxy resins obtained from amines and epichlorohydrin, vinylcyclohexene dioxide, 1,4-butanediol diglycidyl ether, 1,6-hexanesiol diglycidyl ether, etc.
（ポリアミン）
（Ｂ）成分の西宮ｎｎポリアミンは、芳香族ジアルデヒ
ド１モルに対し、
一般式
〔式中、Ｘは水素原子、ハロゲン原子または炭素２文１
〜４のアルキル基もしくはアルコキシ塾である〕
で示される芳１ダ族アミンを２〜６０モルの割合で反応
させて得られる前記一般式（１）で示されるポリアミン
を主成分とするものである（特開昭５８−２２５０４３
号公報参照）。(Polyamine) The Nishinomiya nn polyamine of the component (B) has the general formula [wherein, X is a hydrogen atom, a halogen atom, or a carbon 2 carbon 1
~4 alkyl group or alkoxy group] The main component is a polyamine represented by the general formula (1) obtained by reacting an aromatic amine represented by 2 to 60 moles in a proportion of 2 to 60 moles. (Unexamined Japanese Patent Publication No. 58-225043
(see publication).
原料の芳香族ジアルデヒドとしては、下記−〆α式
で示される化合物、具体的には１，２−ベンゼンジアル
デヒド、１．３−ベンゼンジアルデヒド、１．４−ベン
ゼンジアルデヒドが好ましく、これにノ・ロゲン基、ア
ルキル法等の置換基を有するものであつてもよい。The aromatic dialdehyde used as a raw material is preferably a compound represented by the formula -α below, specifically 1,2-benzenedialdehyde, 1,3-benzenedialdehyde, or 1,4-benzenedialdehyde. It may also have a substituent such as a norogen group or an alkyl group.
また、芳香族アミンとしては、アニリン、ｏ −トルイ
ジン、ｍ−トルイジン、ｐ−トルイジン、０−エチルア
ニリン、Ｏ−イソプロピルアニリン、ｐ−ブチルアニリ
ン、Ｏ−アニシジン、ｍ−アニシジン、ｐ−アニシジン
、０−フェネチジン、りａルアニリン類、ブロムアニリ
ン類等が挙げられる。In addition, the aromatic amines include aniline, o-toluidine, m-toluidine, p-toluidine, 0-ethylaniline, O-isopropylaniline, p-butylaniline, O-anisidine, m-anisidine, p-anisidine, -Phenetidine, ralanilines, bromoanilines and the like.
芳香族ジアルデヒドと芳香族アミンとの反応は、塩酸、
硫酸等の鉱酸類、蓚酸、バラトルエンスルフォン酸等の
有機酸類、その池の有機酸塩類等の酸性触媒の存在下に
、芳香族ジアルデヒド １モルに討して、芳香族アミン
２〜６０モル、好ましくは５〜５０モルの割合で４０
〜１５０℃の温度で、１〜１０時間縮時間縮合行う。The reaction between aromatic dialdehyde and aromatic amine is carried out using hydrochloric acid,
In the presence of an acidic catalyst such as mineral acids such as sulfuric acid, organic acids such as oxalic acid and balatoluenesulfonic acid, and organic acid salts thereof, 1 mole of aromatic dialdehyde is mixed with 2 to 60 moles of aromatic amine. , preferably in a proportion of 5 to 50 mol.
Condensation is carried out at a temperature of ~150° C. for a time of 1 to 10 hours.
反応終了後、反応混合物を水酸化す） ＩＪウムで代表
されるアルカリを用いて中和し、水洗を行った後に過剰
の芳香族アミンを減圧除去することによりポリアミンを
イ４ることができる。After the reaction is completed, the reaction mixture is hydroxylated) The polyamine can be purified by neutralizing it with an alkali such as IJum, washing with water, and removing excess aromatic amine under reduced pressure.
得られるポリアミンは常温で固体であり、前記一般式中
で示される構造を有するものが６０重量５以上である。The resulting polyamine is solid at room temperature, and has a structure represented by the above general formula with a weight of 60% or more.
この式（１）で示されるポリアミンの他に、この式（１
）で示されるポリアミンに更に芳爵族アルデヒドが縮合
反応し、それに更に芳香族アミンが反応したＮＨ２基を
７以上有する次式（Ｉｎで示されるポリアミンが４０重
吐％以下の割合で得られる。In addition to the polyamine represented by this formula (1), this formula (1)
) is further subjected to a condensation reaction with an aromatic aldehyde, and a polyamine represented by the following formula (In) having 7 or more NH2 groups further reacted with an aromatic amine is obtained at a rate of 40% or less.
ＮＨ２ＮＦＬＩ
〔式中のＸは（Ｉ）式と同じであ抄、Ｙｌ、 Ｙｌ、Ｙ
３、Ｙ４はＨまたは
であ抄、ｙ１／、Ｙ２′、Ｙ３′けＨまたはであり、Ｙ
ｌ“、Ｙｌ“、Ｙ３ はＨまたけである〕。NH2NFLI [X in the formula is the same as in formula (I);
3, Y4 is H or y1/, Y2', Y3' is H or
l", Yl", Y3 are H straddles].
これらＮＨ２基を７個以上有するポリアミンの存在ハケ
ルパーミエーシミンクロマトグラ７により確認された。The presence of polyamines having seven or more NH2 groups was confirmed by Hakel Permie Simin Chromatography 7.
この■成分のポリアミンの配合清は、（囚成分のエポキ
シ化合物ｘｏｏ重ｒｔ部に対し、１〜１００重夛部、好
ましくは、５〜６０重量部の割合で使用される。The composition of the polyamine as component (1) is used in an amount of 1 to 100 parts by weight, preferably 5 to 60 parts by weight, based on rt parts by weight of the epoxy compound as the carrier component.
（任意成分）
本発明の耐熱性組成物には、必要に応じて次の成分を添
加することができる。(Optional Components) The following components can be added to the heat-resistant composition of the present invention as necessary.
（１）粉末状の補強剤や充てん剤、たとえば酸化アルミ
ニウム、酸化マグネシウムなどの金属酸化物、水酸化ア
ルミニウムなどの金属水ｒ；ｖ化物、炭酸カルシウム、
炭酸マグネシウムなど金属炭酸塩、ケイソウ土粉、塩基
性ケイ・・１１マグネシウム、焼成りレイ、微粉末シリ
カ、溶融シリカ、結晶シリカ、カーボンブラック、カオ
リン、９扮末マイカ、石英粉末、水酸化アルミニウムな
どの金属水酸化物、グラファイト、アスベスト、二流化
モリブデン、三酸化アンチモンなど。さらに繊維質の補
強材や充てん剤、たとえばガラス繊維、ロックウール、
セラミック繊維アスベスト、およびカーボンファイバー
などの無機質繊維や紙、パルプ、木粉、リンターならび
にポリアミド繊維などの合成ｆ、５！准などである。こ
れらの粉末もしく・：ハ繊Ｆｆｉ ’Ｉ！！［の補強材
や充てん剤の更用騎は用途により異なるが積層材料や成
形材料としては■との）成分の和の樹ｑ旨１徂成物１０
０重位部に討して５００７１［１部まで使用できる。(1) Powdered reinforcing agents and fillers, such as metal oxides such as aluminum oxide and magnesium oxide, metal hydroxides such as aluminum hydroxide, hydroxides, calcium carbonate,
Metal carbonates such as magnesium carbonate, diatomaceous earth powder, basic silica...11 magnesium, fired clay, fine powder silica, fused silica, crystalline silica, carbon black, kaolin, powdered mica, quartz powder, aluminum hydroxide, etc. metal hydroxides, graphite, asbestos, molybdenum distributide, antimony trioxide, etc. In addition, fibrous reinforcements and fillers such as glass fiber, rock wool,
Synthetic fibers such as ceramic fiber asbestos, inorganic fibers such as carbon fiber, paper, pulp, wood flour, linters, and polyamide fibers f, 5! etc. These powders or...:Hasen Ffi 'I! ! [Replacement of reinforcing materials and fillers varies depending on the application, but as laminated materials and molding materials,
Up to 1 part of 50071 can be used.
（２）着色剤、顔料、難燃剤たとえば二１浚化チタン、
′Ｒ鉛カーボンブラック、鉄黒、モリブデン赤、紺＃、
弾け、カドミウム黄、カドミウム赤、赤リン等の無機リ
ン、トリフェニルフォスフエイト等の有機リンなどであ
る。(2) Colorants, pigments, flame retardants such as 21 dredged titanium,
'R lead carbon black, iron black, molybdenum red, navy blue #,
These include inorganic phosphorus such as pop, cadmium yellow, cadmium red, and red phosphorus, and organic phosphorus such as triphenyl phosphate.
（３）さらに、最終的な傘膜、接着層、樹脂成形品など
における樹脂の性質を改善する目的で種々の合成樹脂を
配合することができる。たとえばフェノール樹脂、アル
キド「」脂、メラミン樹脂、フッ素樹脂、塩化ビニル樹
脂、アクリル樹脂、シリコーン樹脂、ポリエステル樹脂
等の１種または２種以上の組み合せを挙げることができ
る。これらの樹脂の使用量は本発明の樹脂組成物本来の
性質を損わない範囲駄、すなわち、全樹脂肴の５０重危
％未滴が好ましい。(3) Furthermore, various synthetic resins can be blended for the purpose of improving the properties of the resin in the final umbrella film, adhesive layer, resin molded product, etc. Examples include one or a combination of two or more of phenol resins, alkyd resins, melamine resins, fluororesins, vinyl chloride resins, acrylic resins, silicone resins, polyester resins, and the like. The amount of these resins to be used is preferably within a range that does not impair the inherent properties of the resin composition of the present invention, that is, 50% of the total resin composition.
囚成分、［Ｆ］）ｒＪｔ分および各種添加剤の配合手段
としては、加熱溶融混合、ロール、ニーダ−等を用いて
の混諌、適当な有機溶剤を用いての混合及び乾式混合等
があげられる。Examples of methods for blending the prison component, [F]) rJt component, and various additives include heating and melt mixing, mixing using a roll, kneader, etc., mixing using an appropriate organic solvent, and dry mixing. It will be done.
本発明の・け熱性エポキシ樹脂組成物は、従来の芳香族
アミン硬化物と比較して；・村熱性に優れる硬化物を与
える。The heat-resistant epoxy resin composition of the present invention provides a cured product with excellent heat resistance compared to conventional aromatic amine cured products.
以下、実：倹例により本発明を更に詳細に説明する。 Hereinafter, the present invention will be explained in more detail with reference to practical examples.
ポリアミンの製造例
例１
昌度計、冷却得、攪拌装置を備えた三ロフラスコ内に１
，３−ベンゼンジアルデヒ）’ ３０ ｆ （０，２２
４モル）、アニリン１６６．６ ｔ （１，７９モル）
、濃塩酸６．８ｆを仕込み、水の還流化（温度１０７℃
）で５時間反応させた。Production Example of Polyamine Example 1 1 in a three-ring flask equipped with a centimeter, a cooling device, and a stirring device.
,3-benzenedialdehy)' 30 f (0,22
4 mol), aniline 166.6 t (1,79 mol)
, 6.8f of concentrated hydrochloric acid was charged, and the water was refluxed (temperature: 107°C).
) for 5 hours.
反応終了後、２０％の水酸化す） ＩＪウム水溶液２０
２を加え、５分間攪拌を続は中和反応を行った。次に、
メチルイソブチルケトン５００１Ｆを加え、析出物をｔ
Ｗ解した後、純水３００１で計３回水洗を行い、副生し
た塩化す） ＩＪウム及び過剰の水鑓化ナトリウムを除
去した。After the reaction is complete, add 20% hydroxide) IJium aqueous solution 20
2 was added and stirred for 5 minutes, followed by a neutralization reaction. next,
Add methyl isobutyl ketone 5001F and remove the precipitate.
After dissolving with W, it was washed with pure water 3001 three times in total to remove by-produced sodium chloride and excess sodium chloride.
次いで、容屏液を減圧下（１００〜１ ｒｍ ｆ（ｇ／
８０〜１８０℃）でメチルインブチルケトン及び未反応
のアニＩＪンを完全に除去し、残留物を１８０℃で流し
出し、冷却して橙色透明な次式で示されるポリアミンを
７７％有するポリアミンの混合物１０１．１ ｆを得た
。Next, the liquid was heated under reduced pressure (100 to 1 rmf (g/
Methyl imbutyl ketone and unreacted nitrogen were completely removed at 180° C.), the residue was poured out at 180° C., and the residue was cooled to form an orange transparent polyamine having 77% of the polyamine represented by the following formula. A mixture 101.1 f was obtained.
（以丁者白）
このポリアミンの軟化点（毛細管法）は１１５〜１２１
℃、中和当量は１１８であった。(Itasha Haku) The softening point (capillary method) of this polyamine is 115-121
℃, the neutralization equivalent was 118.
例２
１．４−ベンゼンジアルデヒド３０ ｆ （０，２２４
モル）、０−トルイジン９５．９ Ｆ （０，８９５モ
ル）およびアニリン８３．３１Ｆ（０，８９５モル）を
漿料として用いる他は実鴇例１と同様にして赤色ｄ明な
固体のポリアミンを１１１．９９得た。Example 2 1,4-benzenedialdehyde 30 f (0,224
A bright red solid polyamine was prepared in the same manner as in Example 1 except that 95.9 F (0,895 mol) of 0-toluidine (0,895 mol) and 83.31 F (0,895 mol) of aniline were used as the active ingredients. I got 111.99.
このポリアミンの軟化点は１２２〜１２８℃であり、中
和当量は１２６であった。The softening point of this polyamine was 122 to 128°C, and the neutralization equivalent was 126.
実施例１
油化シェルエポキシ（働製ビスフェノールＡのジグリシ
ジルエーテル１エピコート８２８”（商品名）１００重
量部と、製造例１で得たポリアミン３１．１ ｉｉ部を
温度１３０℃で混合し、脱泡後、金属の型内に流し込み
、１５０℃で３時間、次いで２００℃で１０時間硬化を
行い、縦１２７ｍｍ、１黄１２．７ｆｌ、厚さ６．４瓢
の硬化物を得た。この硬化物の・勿注値を表１に示す。Example 1 100 parts by weight of oil-based shell epoxy (Diglycidyl Ether 1 of Bisphenol A 1 Epicote 828'' (trade name) manufactured by Kirin Co., Ltd.) and 31.1 parts of the polyamine obtained in Production Example 1 were mixed at a temperature of 130°C, and desorbed. After foaming, it was poured into a metal mold and cured at 150°C for 3 hours and then at 200°C for 10 hours to obtain a cured product with a length of 127 mm, 1 yellow of 12.7 fl, and a thickness of 6.4 gourd. Table 1 shows the values of the materials.
実施例２
ポリアミンとして製造例２で得たポリアミンを３２．６
電歇部用いる他は実施例１と同様にして表１に示す硬化
物を得た。Example 2 The polyamine obtained in Production Example 2 was used as a polyamine at 32.6
A cured product shown in Table 1 was obtained in the same manner as in Example 1 except that an electric switch was used.
実６１例３〜８、比較例１〜２
表１に示すエポキシ化合物およびポリアミンを用いる曲
は実施例１と同様にして硬化物を得た。Example 61 Examples 3 to 8, Comparative Examples 1 to 2 For songs using the epoxy compounds and polyamines shown in Table 1, cured products were obtained in the same manner as in Example 1.
結果を表１に示す。The results are shown in Table 1.
（以下余白）
実施例９
日本化薬■製りレゾールノボラツクエボキシ樹脂“ＥＯ
ＣＮ−１０３１（＠品名）１００直債部、例１で得られ
たポリアミン２６重計部および溶融シリカ２００重量部
を９０〜１１０℃の加熱ロールを用いて１０分間混練し
た。(Left below) Example 9 Resol novolac epoxy resin “EO” manufactured by Nippon Kayaku ■
100 straight parts of CN-1031 (@product name), 26 weight parts of the polyamine obtained in Example 1, and 200 weight parts of fused silica were kneaded for 10 minutes using heated rolls at 90 to 110°C.
この混合物を粉砕機で粉砕して粒状化し、粒状物を加熱
プレスを用いて１８０Ｃ，１０分間、圧力５ｏｈｌ／ｄ
の条件で圧縮成形を行い、縦１２７■、ｆＡ １２．７
ｔｒａｍ、厚さ６．４ｍの成形物を得た。This mixture was pulverized into granules using a pulverizer, and the granules were heated at 180C for 10 minutes at a pressure of 5ohl/d.
Compression molding was performed under the following conditions, length: 127 cm, fA: 12.7
A molded product with a thickness of 6.4 m was obtained.
この成形物を更に２００℃のオープンにて１０時間後硬
化させ、表２に示す物性の硬化物を得た。This molded product was further post-cured at 200° C. for 10 hours to obtain a cured product having the physical properties shown in Table 2.
実施例１０
ポリアミンとして例２で得たポリアミンを２８重縫部用
いる他は実施例９と同様にして表２に示す史化９勿を得
た。Example 10 The same procedure as in Example 9 was carried out, except that the polyamine obtained in Example 2 was used as the polyamine for 28 double stitches, to obtain a fabricated material shown in Table 2.
比紋列３
ポリアミンとして４，４′−ジアミノジフェニルメタン
２２’ｉｌｊ欧部用いる他は実施例９と同様にしてべ２
に示す硬化物を得た。Ratio 3: Proceed in the same manner as in Example 9 except that 4,4'-diaminodiphenylmethane 22'ilj is used as the polyamine.
A cured product shown in was obtained.
表−２ 特許出７頭人 三菱油化株式会社 代理人 弁理士 古 川 秀 利 Ｉ 長谷正久Table-2 Seven patentees: Mitsubishi Yuka Co., Ltd. Agent: Patent Attorney Hidetoshi Furukawa I Masahisa Hase
Claims (1)
有するエポキシ化合物 （Ｂ）成分：下記一般式で示されるポリアミン▲数式、
化学式、表等があります▼ 〔式中、Ｘは水素原子、ハロゲン原子または炭素数１〜
４のアルキル基もしくはアルコキシ基である〕 上記（Ａ）および（Ｂ）成分が配合されていることを特
徴とする耐熱性エポキシ樹脂組成物。[Claims] Component (A): Epoxy compound having at least two epoxy groups in one molecule (B) Component: Polyamine represented by the following general formula ▲ Numerical formula,
There are chemical formulas, tables, etc.▼ [In the formula, X is a hydrogen atom, a halogen atom, or a carbon number of 1 to
4]] A heat-resistant epoxy resin composition characterized in that the above-mentioned components (A) and (B) are blended.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7049186A JPS62227920A (en) | 1986-03-28 | 1986-03-28 | Heat-resistant epoxy resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7049186A JPS62227920A (en) | 1986-03-28 | 1986-03-28 | Heat-resistant epoxy resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62227920A true JPS62227920A (en) | 1987-10-06 |
Family
ID=13433038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7049186A Pending JPS62227920A (en) | 1986-03-28 | 1986-03-28 | Heat-resistant epoxy resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62227920A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011146106A1 (en) | 2010-05-21 | 2011-11-24 | Dow Global Technologies Llc | Hardeners for thermosettable resin compositions |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58225043A (en) * | 1982-06-22 | 1983-12-27 | Mitsubishi Petrochem Co Ltd | Preparation of polyamine |
-
1986
- 1986-03-28 JP JP7049186A patent/JPS62227920A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58225043A (en) * | 1982-06-22 | 1983-12-27 | Mitsubishi Petrochem Co Ltd | Preparation of polyamine |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011146106A1 (en) | 2010-05-21 | 2011-11-24 | Dow Global Technologies Llc | Hardeners for thermosettable resin compositions |
| US8865917B2 (en) | 2010-05-21 | 2014-10-21 | Dow Global Technologies Llc | Hardeners for thermosettable resin compositions |
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