DE19828248A1 - Bei niedriger Temperatur härtende Epoxidharzsysteme aus Aminoglycidylverbindungen und cyclischen Carbonsäureanhydriden - Google Patents
Bei niedriger Temperatur härtende Epoxidharzsysteme aus Aminoglycidylverbindungen und cyclischen CarbonsäureanhydridenInfo
- Publication number
- DE19828248A1 DE19828248A1 DE19828248A DE19828248A DE19828248A1 DE 19828248 A1 DE19828248 A1 DE 19828248A1 DE 19828248 A DE19828248 A DE 19828248A DE 19828248 A DE19828248 A DE 19828248A DE 19828248 A1 DE19828248 A1 DE 19828248A1
- Authority
- DE
- Germany
- Prior art keywords
- epoxy resin
- low temperature
- temperature curing
- systems according
- resin systems
- 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.)
- Ceased
Links
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 67
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 65
- 238000013035 low temperature curing Methods 0.000 title claims abstract description 28
- 239000000853 adhesive Substances 0.000 title description 17
- 230000001070 adhesive effect Effects 0.000 title description 17
- 229920005989 resin Polymers 0.000 title description 11
- 239000011347 resin Substances 0.000 title description 11
- 238000005266 casting Methods 0.000 title description 3
- 239000011159 matrix material Substances 0.000 title description 3
- -1 aminoglycidyl compound Chemical class 0.000 claims abstract description 52
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 7
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 45
- 238000001723 curing Methods 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 150000008064 anhydrides Chemical group 0.000 claims description 28
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- 239000003795 chemical substances by application Substances 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 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 claims description 10
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 10
- 239000004593 Epoxy Substances 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims description 6
- 150000002596 lactones Chemical class 0.000 claims description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
- 239000011976 maleic acid Substances 0.000 claims description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 5
- FAUAZXVRLVIARB-UHFFFAOYSA-N 4-[[4-[bis(oxiran-2-ylmethyl)amino]phenyl]methyl]-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC(CC=2C=CC(=CC=2)N(CC2OC2)CC2OC2)=CC=1)CC1CO1 FAUAZXVRLVIARB-UHFFFAOYSA-N 0.000 claims description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 4
- 150000003972 cyclic carboxylic anhydrides Chemical class 0.000 claims description 4
- FLBJFXNAEMSXGL-UHFFFAOYSA-N het anhydride Chemical compound O=C1OC(=O)C2C1C1(Cl)C(Cl)=C(Cl)C2(Cl)C1(Cl)Cl FLBJFXNAEMSXGL-UHFFFAOYSA-N 0.000 claims description 4
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 claims description 4
- 229920003986 novolac Polymers 0.000 claims description 4
- 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 claims description 3
- OXQXGKNECHBVMO-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound C1C(C(=O)O)CCC2OC21 OXQXGKNECHBVMO-UHFFFAOYSA-N 0.000 claims description 3
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- 239000011353 cycloaliphatic epoxy resin Substances 0.000 claims description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 2
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 claims description 2
- 229930003836 cresol Natural products 0.000 claims description 2
- ILUAAIDVFMVTAU-UHFFFAOYSA-N cyclohex-4-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CC=CCC1C(O)=O ILUAAIDVFMVTAU-UHFFFAOYSA-N 0.000 claims description 2
- 239000003063 flame retardant Substances 0.000 claims description 2
- 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 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
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- 150000002989 phenols Chemical class 0.000 claims description 2
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- ZMPRRFPMMJQXPP-UHFFFAOYSA-N 2-sulfobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1S(O)(=O)=O ZMPRRFPMMJQXPP-UHFFFAOYSA-N 0.000 claims 1
- NSJAWXMCLJVBPM-UHFFFAOYSA-N 3-butyloxolane-2,5-dione Chemical compound CCCCC1CC(=O)OC1=O NSJAWXMCLJVBPM-UHFFFAOYSA-N 0.000 claims 1
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 claims 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims 1
- 229940091173 hydantoin Drugs 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 16
- 239000004848 polyfunctional curative Substances 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 6
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- 238000000034 method Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
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- 238000002411 thermogravimetry Methods 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- 229940106691 bisphenol a Drugs 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
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- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000005554 pickling Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 description 2
- NCYNKWQXFADUOZ-UHFFFAOYSA-N 1,1-dioxo-2,1$l^{6}-benzoxathiol-3-one Chemical compound C1=CC=C2C(=O)OS(=O)(=O)C2=C1 NCYNKWQXFADUOZ-UHFFFAOYSA-N 0.000 description 2
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 2
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 2
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- 229910000838 Al alloy Inorganic materials 0.000 description 2
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- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
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- 150000007513 acids Chemical class 0.000 description 2
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- 125000002619 bicyclic group Chemical group 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
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- 229920006332 epoxy adhesive Polymers 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- MUTGBJKUEZFXGO-UHFFFAOYSA-N hexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21 MUTGBJKUEZFXGO-UHFFFAOYSA-N 0.000 description 2
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- KJMRWDHBVCNLTQ-UHFFFAOYSA-N N-methylisatoic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)N(C)C2=C1 KJMRWDHBVCNLTQ-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000004844 aliphatic epoxy resin Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical compound CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- CURBACXRQKTCKZ-UHFFFAOYSA-N cyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C1C(O)=O CURBACXRQKTCKZ-UHFFFAOYSA-N 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004870 electrical engineering Methods 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011151 fibre-reinforced plastic Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- MCQOWYALZVKMAR-UHFFFAOYSA-N furo[3,4-b]pyridine-5,7-dione Chemical compound C1=CC=C2C(=O)OC(=O)C2=N1 MCQOWYALZVKMAR-UHFFFAOYSA-N 0.000 description 1
- KFKMGUPDWTWQFM-UHFFFAOYSA-N furo[3,4-c]pyridine-1,3-dione Chemical compound N1=CC=C2C(=O)OC(=O)C2=C1 KFKMGUPDWTWQFM-UHFFFAOYSA-N 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000004849 latent hardener Substances 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- MERIEQHLDYSVSR-UHFFFAOYSA-N n-[[2-[[bis(oxiran-2-ylmethyl)amino]methyl]phenyl]methyl]-1-(oxiran-2-yl)-n-(oxiran-2-ylmethyl)methanamine Chemical compound C1OC1CN(CC=1C(=CC=CC=1)CN(CC1OC1)CC1OC1)CC1CO1 MERIEQHLDYSVSR-UHFFFAOYSA-N 0.000 description 1
- OBKARQMATMRWQZ-UHFFFAOYSA-N naphthalene-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 OBKARQMATMRWQZ-UHFFFAOYSA-N 0.000 description 1
- HDLRSIQOZFLEPK-UHFFFAOYSA-N naphthalene-1,2,5,8-tetracarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C2=C(C(O)=O)C(C(=O)O)=CC=C21 HDLRSIQOZFLEPK-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 description 1
- UFOIOXZLTXNHQH-UHFFFAOYSA-N oxolane-2,3,4,5-tetracarboxylic acid Chemical compound OC(=O)C1OC(C(O)=O)C(C(O)=O)C1C(O)=O UFOIOXZLTXNHQH-UHFFFAOYSA-N 0.000 description 1
- 229960004065 perflutren Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- RTHVZRHBNXZKKB-UHFFFAOYSA-N pyrazine-2,3,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=NC(C(O)=O)=C(C(O)=O)N=C1C(O)=O RTHVZRHBNXZKKB-UHFFFAOYSA-N 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- JIYNFFGKZCOPKN-UHFFFAOYSA-N sbb061129 Chemical compound O=C1OC(=O)C2C1C1C=C(C)C2C1 JIYNFFGKZCOPKN-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- LUEGQDUCMILDOJ-UHFFFAOYSA-N thiophene-2,3,4,5-tetracarboxylic acid Chemical compound OC(=O)C=1SC(C(O)=O)=C(C(O)=O)C=1C(O)=O LUEGQDUCMILDOJ-UHFFFAOYSA-N 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3227—Compounds containing acyclic nitrogen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T29/00—Metal working
- Y10T29/49—Method of mechanical manufacture
- Y10T29/49002—Electrical device making
- Y10T29/49117—Conductor or circuit manufacturing
- Y10T29/49169—Assembling electrical component directly to terminal or elongated conductor
- Y10T29/49171—Assembling electrical component directly to terminal or elongated conductor with encapsulating
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T29/00—Metal working
- Y10T29/49—Method of mechanical manufacture
- Y10T29/49002—Electrical device making
- Y10T29/49227—Insulator making
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Indole Compounds (AREA)
- Valve Housings (AREA)
- Extrusion Moulding Of Plastics Or The Like (AREA)
- Paints Or Removers (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19828248A DE19828248A1 (de) | 1998-06-25 | 1998-06-25 | Bei niedriger Temperatur härtende Epoxidharzsysteme aus Aminoglycidylverbindungen und cyclischen Carbonsäureanhydriden |
| AU42549/99A AU764356B2 (en) | 1998-06-25 | 1999-06-25 | Resin system |
| KR1020007014672A KR20010071583A (ko) | 1998-06-25 | 1999-06-25 | 수지계 |
| AT99957171T ATE255611T1 (de) | 1998-06-25 | 1999-06-25 | Harzsystem |
| PCT/CH1999/000275 WO1999067315A1 (de) | 1998-06-25 | 1999-06-25 | Harzsystem |
| JP2000555963A JP2002518567A (ja) | 1998-06-25 | 1999-06-25 | 樹脂系 |
| CA002334824A CA2334824C (en) | 1998-06-25 | 1999-06-25 | Resin system |
| EP99957171A EP1091992B1 (de) | 1998-06-25 | 1999-06-25 | Harzsystem |
| DE59907948T DE59907948D1 (de) | 1998-06-25 | 1999-06-25 | Harzsystem |
| US09/720,158 US6468659B1 (en) | 1998-06-25 | 1999-06-25 | Resin system |
| CNB998098663A CN1142960C (zh) | 1998-06-25 | 1999-06-25 | 树脂体系 |
| ZA200007392A ZA200007392B (en) | 1998-06-25 | 2000-12-12 | Resin system. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19828248A DE19828248A1 (de) | 1998-06-25 | 1998-06-25 | Bei niedriger Temperatur härtende Epoxidharzsysteme aus Aminoglycidylverbindungen und cyclischen Carbonsäureanhydriden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19828248A1 true DE19828248A1 (de) | 1999-12-30 |
Family
ID=7871932
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19828248A Ceased DE19828248A1 (de) | 1998-06-25 | 1998-06-25 | Bei niedriger Temperatur härtende Epoxidharzsysteme aus Aminoglycidylverbindungen und cyclischen Carbonsäureanhydriden |
| DE59907948T Expired - Fee Related DE59907948D1 (de) | 1998-06-25 | 1999-06-25 | Harzsystem |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59907948T Expired - Fee Related DE59907948D1 (de) | 1998-06-25 | 1999-06-25 | Harzsystem |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6468659B1 (https=) |
| EP (1) | EP1091992B1 (https=) |
| JP (1) | JP2002518567A (https=) |
| KR (1) | KR20010071583A (https=) |
| CN (1) | CN1142960C (https=) |
| AT (1) | ATE255611T1 (https=) |
| AU (1) | AU764356B2 (https=) |
| CA (1) | CA2334824C (https=) |
| DE (2) | DE19828248A1 (https=) |
| WO (1) | WO1999067315A1 (https=) |
| ZA (1) | ZA200007392B (https=) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1213314A1 (de) * | 2000-12-07 | 2002-06-12 | Abb Research Ltd. | Härterkomponente zum Härten von Epoxyharzen |
| EP1331234A1 (de) * | 2002-01-28 | 2003-07-30 | ABB Research Ltd. | Vergussmasse auf der Basis duroplastischer Epoxidharze |
| DE102008000517A1 (de) * | 2008-03-05 | 2009-09-10 | Zf Lenksysteme Gmbh | Verfahren zur Herstellung einer druckdichten Fügeverbindung eines metallischen Bauteils mit einem Kunststoffbauteil |
| DE102014216437A1 (de) * | 2014-08-19 | 2016-02-25 | Siemens Aktiengesellschaft | Epoxidharz-Formulierung, Epoxidharz daraus und Verwendungen dazu |
| WO2021207777A1 (de) * | 2020-04-17 | 2021-10-21 | Polymer Competence Center Leoben Gmbh | Aushärtbare zusammensetzung zur herstellung eines vitrimers und daraus erhältliches vitrimer und verfahren zu dessen herstellung |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6617698B2 (en) * | 2001-03-09 | 2003-09-09 | International Business Machines Corporation | Reworkable and thermally conductive adhesive and use thereof |
| US7129318B2 (en) * | 2003-09-02 | 2006-10-31 | I.S.T. (Ma) Corporation | RTM and RI processable polyimide resins |
| KR100570209B1 (ko) * | 2003-10-15 | 2006-04-12 | 주식회사 하이닉스반도체 | 유기 반사방지막용 광 흡수제 중합체 및 이의 제조 방법과상기 중합체를 포함하는 유기 반사 방지막 조성물 |
| CN100451080C (zh) * | 2004-05-26 | 2009-01-14 | 北京韩创科建筑材料科技有限公司 | 改性双组份环氧树脂涂料 |
| JP4711119B2 (ja) * | 2005-06-14 | 2011-06-29 | 日立化成工業株式会社 | 電気絶縁用樹脂組成物及びそれを用いた電気機器 |
| TWI414519B (zh) * | 2006-08-09 | 2013-11-11 | Mitsubishi Gas Chemical Co | 酸酐酯與其組成物、熱硬化性樹脂組成物及其硬化物 |
| JP4395547B1 (ja) * | 2008-11-06 | 2010-01-13 | 地方独立行政法人 岩手県工業技術センター | 偏光レンズ及び偏光レンズの製造方法 |
| CN102725802B (zh) * | 2010-02-03 | 2016-04-06 | Abb研究有限公司 | 电绝缘体系 |
| FR2960472B1 (fr) * | 2010-05-31 | 2012-09-28 | Arkema France | Procede d'assemblage et de reparation d'objets a base de resine epoxy |
| CN101935388B (zh) * | 2010-09-16 | 2012-04-25 | 中国人民解放军国防科学技术大学 | 树脂组合物及其在复合材料线芯制备中的应用 |
| JP5606870B2 (ja) * | 2010-10-25 | 2014-10-15 | 日本化薬株式会社 | エポキシ樹脂組成物及びその硬化物 |
| WO2012158291A1 (en) | 2011-05-13 | 2012-11-22 | Dow Global Technologies Llc | Insulation formulations |
| US9196412B2 (en) | 2011-05-13 | 2015-11-24 | Dow Global Technologies Llc | Insulation formulations |
| DE102012211323A1 (de) | 2012-06-29 | 2014-01-02 | Evonik Industries Ag | Härter für Epoxidharzsysteme und deren Verwendung |
| KR20140008871A (ko) * | 2012-07-12 | 2014-01-22 | 삼성전기주식회사 | 빌드업 절연필름용 에폭시 수지 조성물, 이로부터 제조된 절연 필름 및 이를 구비한 다층 인쇄회로기판 |
| US20150189745A1 (en) * | 2012-09-14 | 2015-07-02 | Shengyi Technology Co., Ltd. | Epoxy resin composition, and, prepreg and copper clad laminate manufactured using the composition |
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| WO2016145647A1 (en) * | 2015-03-19 | 2016-09-22 | Ablestik (Shanghai) Ltd. | Epoxy molding compound using anhydride hardener, manufacturing process and use thereof |
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| US4595623A (en) * | 1984-05-07 | 1986-06-17 | Hughes Aircraft Company | Fiber-reinforced syntactic foam composites and method of forming same |
| DE4040471A1 (de) * | 1990-08-01 | 1992-02-06 | Bayer Ag | Haertbare mischungen zur herstellung von epoxidnetzwerken, verfahren zu deren herstellung und verwendung |
| US5629379A (en) * | 1994-09-27 | 1997-05-13 | Harper; John D. | Anhydride-hardened epoxy resin with polybutadiene-maleic anhydride adduct |
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| DE1019083B (de) | 1956-01-28 | 1957-11-07 | Bayer Ag | Verfahren zur Herstellung von Kunststoffen durch Haerten von Epoxyverbindungen |
| DE1251036B (de) | 1961-05-12 | 1967-09-28 | General Aniline &. Film Corpora tion New York, N Y (V St A) | Verfahren zur Herstellung von Formkorpern |
| US3222321A (en) | 1962-08-16 | 1965-12-07 | Soto Chemical Coatings Inc De | Modified acrylamide interpolymers containing interpolymerized unsaturated epoxy resins |
| US3683044A (en) | 1969-12-29 | 1972-08-08 | Japan Gas Chemical Co | Heat-curable composition comprising polyglycidyl xylylene-diamine and process for preparation of polyglycidyl xylylenediamine |
| JPS5111897A (ja) * | 1974-07-19 | 1976-01-30 | Hitachi Chemical Co Ltd | Kokaseiehokishijushisoseibutsu |
| JPS6038421A (ja) | 1983-08-11 | 1985-02-28 | Mitsubishi Petrochem Co Ltd | エポキシ樹脂組成物 |
| US4559272A (en) | 1984-05-09 | 1985-12-17 | Hughes Aircraft Company | Heat curable polyglycidyl aromatic amine encapsulants |
| US4916202A (en) * | 1987-09-17 | 1990-04-10 | University Of Dayton | Epoxy resin |
| GB9010221D0 (en) | 1990-05-05 | 1990-06-27 | Ciba Geigy Ag | N-glycidyl compounds |
| US5111897A (en) | 1990-09-27 | 1992-05-12 | Bridge Weighing Systems, Inc. | Bridge weigh-in-motion system |
-
1998
- 1998-06-25 DE DE19828248A patent/DE19828248A1/de not_active Ceased
-
1999
- 1999-06-25 JP JP2000555963A patent/JP2002518567A/ja active Pending
- 1999-06-25 WO PCT/CH1999/000275 patent/WO1999067315A1/de not_active Ceased
- 1999-06-25 CN CNB998098663A patent/CN1142960C/zh not_active Expired - Fee Related
- 1999-06-25 AU AU42549/99A patent/AU764356B2/en not_active Ceased
- 1999-06-25 EP EP99957171A patent/EP1091992B1/de not_active Expired - Lifetime
- 1999-06-25 DE DE59907948T patent/DE59907948D1/de not_active Expired - Fee Related
- 1999-06-25 AT AT99957171T patent/ATE255611T1/de not_active IP Right Cessation
- 1999-06-25 KR KR1020007014672A patent/KR20010071583A/ko not_active Withdrawn
- 1999-06-25 CA CA002334824A patent/CA2334824C/en not_active Expired - Fee Related
- 1999-06-25 US US09/720,158 patent/US6468659B1/en not_active Expired - Fee Related
-
2000
- 2000-12-12 ZA ZA200007392A patent/ZA200007392B/xx unknown
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| US2884406A (en) * | 1955-10-04 | 1959-04-28 | Bayer Ag | Production of cured epoxide resins |
| DE2650746A1 (de) * | 1975-11-06 | 1977-05-12 | Lord Corp | Epoxyharzmassen |
| US4595623A (en) * | 1984-05-07 | 1986-06-17 | Hughes Aircraft Company | Fiber-reinforced syntactic foam composites and method of forming same |
| DE4040471A1 (de) * | 1990-08-01 | 1992-02-06 | Bayer Ag | Haertbare mischungen zur herstellung von epoxidnetzwerken, verfahren zu deren herstellung und verwendung |
| US5629379A (en) * | 1994-09-27 | 1997-05-13 | Harper; John D. | Anhydride-hardened epoxy resin with polybutadiene-maleic anhydride adduct |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1213314A1 (de) * | 2000-12-07 | 2002-06-12 | Abb Research Ltd. | Härterkomponente zum Härten von Epoxyharzen |
| EP1331234A1 (de) * | 2002-01-28 | 2003-07-30 | ABB Research Ltd. | Vergussmasse auf der Basis duroplastischer Epoxidharze |
| DE102008000517A1 (de) * | 2008-03-05 | 2009-09-10 | Zf Lenksysteme Gmbh | Verfahren zur Herstellung einer druckdichten Fügeverbindung eines metallischen Bauteils mit einem Kunststoffbauteil |
| DE102008000517B4 (de) * | 2008-03-05 | 2018-04-26 | Robert Bosch Automotive Steering Gmbh | Verfahren zum druckdichten Fügen eines metallischen Lenkgetriebegehäuses mit einem Kunststoffgehäusedeckel |
| DE102014216437A1 (de) * | 2014-08-19 | 2016-02-25 | Siemens Aktiengesellschaft | Epoxidharz-Formulierung, Epoxidharz daraus und Verwendungen dazu |
| WO2021207777A1 (de) * | 2020-04-17 | 2021-10-21 | Polymer Competence Center Leoben Gmbh | Aushärtbare zusammensetzung zur herstellung eines vitrimers und daraus erhältliches vitrimer und verfahren zu dessen herstellung |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200007392B (en) | 2001-06-21 |
| CN1313872A (zh) | 2001-09-19 |
| CA2334824A1 (en) | 1999-12-29 |
| AU4254999A (en) | 2000-01-10 |
| AU764356B2 (en) | 2003-08-14 |
| CN1142960C (zh) | 2004-03-24 |
| EP1091992A1 (de) | 2001-04-18 |
| CA2334824C (en) | 2008-01-29 |
| DE59907948D1 (de) | 2004-01-15 |
| EP1091992B1 (de) | 2003-12-03 |
| WO1999067315A1 (de) | 1999-12-29 |
| JP2002518567A (ja) | 2002-06-25 |
| US6468659B1 (en) | 2002-10-22 |
| ATE255611T1 (de) | 2003-12-15 |
| KR20010071583A (ko) | 2001-07-28 |
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| Date | Code | Title | Description |
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| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8122 | Nonbinding interest in granting licences declared | ||
| 8127 | New person/name/address of the applicant |
Owner name: ABB SCHWEIZ AG, BADEN, CH |
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| 8131 | Rejection |