TW503246B - An epoxy resin composition and a process of producing a coated article use thereof - Google Patents
An epoxy resin composition and a process of producing a coated article use thereof Download PDFInfo
- Publication number
- TW503246B TW503246B TW087100801A TW87100801A TW503246B TW 503246 B TW503246 B TW 503246B TW 087100801 A TW087100801 A TW 087100801A TW 87100801 A TW87100801 A TW 87100801A TW 503246 B TW503246 B TW 503246B
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- Prior art keywords
- epoxy resin
- resin composition
- acid
- item
- compound
- Prior art date
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- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 153
- 239000000203 mixture Substances 0.000 title claims abstract description 126
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 100
- 238000000034 method Methods 0.000 title abstract description 29
- 230000008569 process Effects 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 239000002904 solvent Substances 0.000 claims abstract description 52
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000000576 coating method Methods 0.000 claims abstract description 16
- 239000011248 coating agent Substances 0.000 claims abstract description 15
- 229920001577 copolymer Polymers 0.000 claims abstract description 14
- 238000004132 cross linking Methods 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 11
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 7
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 claims abstract description 6
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 claims abstract description 6
- -1 boron Lewis acid Chemical class 0.000 claims description 100
- 239000003054 catalyst Substances 0.000 claims description 86
- 239000000126 substance Substances 0.000 claims description 52
- 239000003112 inhibitor Substances 0.000 claims description 43
- 238000011049 filling Methods 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 229930195733 hydrocarbon Natural products 0.000 claims description 32
- 239000004971 Cross linker Substances 0.000 claims description 25
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 24
- 239000004327 boric acid Substances 0.000 claims description 23
- 150000008064 anhydrides Chemical class 0.000 claims description 20
- 239000004215 Carbon black (E152) Substances 0.000 claims description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
- 230000000269 nucleophilic effect Effects 0.000 claims description 18
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 15
- 239000002841 Lewis acid Substances 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 12
- 239000004970 Chain extender Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 230000001588 bifunctional effect Effects 0.000 claims description 9
- 229910052796 boron Inorganic materials 0.000 claims description 9
- 150000002118 epoxides Chemical class 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 150000007524 organic acids Chemical class 0.000 claims description 9
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 239000011159 matrix material Substances 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001409 amidines Chemical class 0.000 claims description 6
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 229910052785 arsenic Inorganic materials 0.000 claims description 4
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- YZGQDNOIGFBYKF-UHFFFAOYSA-M 2-ethoxyacetate Chemical compound CCOCC([O-])=O YZGQDNOIGFBYKF-UHFFFAOYSA-M 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000003868 ammonium compounds Chemical class 0.000 claims description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
- 238000009792 diffusion process Methods 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 2
- 150000003440 styrenes Chemical group 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 4
- 229920002732 Polyanhydride Polymers 0.000 claims 3
- 239000003733 fiber-reinforced composite Substances 0.000 claims 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 2
- 150000003476 thallium compounds Chemical class 0.000 claims 2
- WLPQCHKXJRHZRI-UHFFFAOYSA-N (2-hydroxybenzoyl) 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1O WLPQCHKXJRHZRI-UHFFFAOYSA-N 0.000 claims 1
- GBBSAMQTQCPOBF-UHFFFAOYSA-N 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane Chemical compound CB1OB(C)OB(C)O1 GBBSAMQTQCPOBF-UHFFFAOYSA-N 0.000 claims 1
- BOGVTNYNTGOONP-UHFFFAOYSA-N 3,4-dihydroxyoxolane-2,5-dione Chemical class OC1C(O)C(=O)OC1=O BOGVTNYNTGOONP-UHFFFAOYSA-N 0.000 claims 1
- 241000219112 Cucumis Species 0.000 claims 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229940126214 compound 3 Drugs 0.000 claims 1
- 239000003431 cross linking reagent Substances 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- YIAVADUIRPWBCA-UHFFFAOYSA-N thallanylidynearsane Chemical compound [Tl]#[As] YIAVADUIRPWBCA-UHFFFAOYSA-N 0.000 claims 1
- 229920005989 resin Polymers 0.000 description 50
- 239000011347 resin Substances 0.000 description 50
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 39
- 150000002430 hydrocarbons Chemical class 0.000 description 29
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 23
- 239000000047 product Substances 0.000 description 18
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 18
- 230000002079 cooperative effect Effects 0.000 description 16
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 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 14
- 238000012545 processing Methods 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 10
- 239000003973 paint Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 9
- 239000011976 maleic acid Substances 0.000 description 9
- 235000006408 oxalic acid Nutrition 0.000 description 9
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 9
- 230000002787 reinforcement Effects 0.000 description 9
- 239000011342 resin composition Substances 0.000 description 9
- 229960004889 salicylic acid Drugs 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- 150000001336 alkenes Chemical class 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 150000002460 imidazoles Chemical class 0.000 description 8
- 235000005985 organic acids Nutrition 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 7
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 7
- 150000001450 anions Chemical class 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 239000002131 composite material Substances 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 150000007517 lewis acids Chemical class 0.000 description 7
- 239000002798 polar solvent Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000002966 varnish Substances 0.000 description 6
- ZFMOJHVRFMOIGF-UHFFFAOYSA-N 2,4,6-trimethoxy-1,3,5,2,4,6-trioxatriborinane Chemical class COB1OB(OC)OB(OC)O1 ZFMOJHVRFMOIGF-UHFFFAOYSA-N 0.000 description 5
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- 238000001879 gelation Methods 0.000 description 5
- 239000004848 polyfunctional curative Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 4
- 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 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 4
- WOLATMHLPFJRGC-UHFFFAOYSA-N furan-2,5-dione;styrene Chemical compound O=C1OC(=O)C=C1.C=CC1=CC=CC=C1 WOLATMHLPFJRGC-UHFFFAOYSA-N 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- CMQUQOHNANGDOR-UHFFFAOYSA-N 2,3-dibromo-4-(2,4-dibromo-5-hydroxyphenyl)phenol Chemical compound BrC1=C(Br)C(O)=CC=C1C1=CC(O)=C(Br)C=C1Br CMQUQOHNANGDOR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 150000004074 biphenyls Chemical class 0.000 description 3
- 150000001638 boron Chemical class 0.000 description 3
- 150000001642 boronic acid derivatives Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000011889 copper foil Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005979 thermal decomposition reaction Methods 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/066—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with chain extension or advancing agents
-
- 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
-
- 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
- C08G59/68—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 catalysts used
- C08G59/72—Complexes of boron halides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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)
- Reinforced Plastic Materials (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3594897P | 1997-01-21 | 1997-01-21 | |
| GBGB9701294.2A GB9701294D0 (en) | 1997-01-22 | 1997-01-22 | Latent catalysts for epoxy curing systems |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW503246B true TW503246B (en) | 2002-09-21 |
Family
ID=26310844
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW087100801A TW503246B (en) | 1997-01-21 | 1998-01-21 | An epoxy resin composition and a process of producing a coated article use thereof |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0954553B2 (enExample) |
| JP (1) | JP4080546B2 (enExample) |
| KR (1) | KR100569617B1 (enExample) |
| CN (1) | CN1129648C (enExample) |
| AT (1) | ATE273348T1 (enExample) |
| DE (1) | DE69825561T3 (enExample) |
| MY (1) | MY128727A (enExample) |
| TW (1) | TW503246B (enExample) |
| WO (1) | WO1998031750A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI496834B (zh) * | 2009-11-06 | 2015-08-21 | Dow Global Technologies Llc | 用於電用層板之儲存穩定的環氧樹脂組成物 |
| TWI613250B (zh) * | 2011-05-02 | 2018-02-01 | 蘭科智慧保護有限責任公司 | 環氧樹脂中之硼酸三甲酯 |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5485487B2 (ja) * | 1999-12-13 | 2014-05-07 | ダウ グローバル テクノロジーズ エルエルシー | 難燃性リン元素含有エポキシ樹脂組成物 |
| US6641923B2 (en) | 2001-07-31 | 2003-11-04 | Ppg Industries Ohio, Inc. | Weldable coating compositions having improved intercoat adhesion |
| US6617400B2 (en) | 2001-08-23 | 2003-09-09 | General Electric Company | Composition of cycloaliphatic epoxy resin, anhydride curing agent and boron catalyst |
| US6617401B2 (en) * | 2001-08-23 | 2003-09-09 | General Electric Company | Composition comprising cycloaliphatic epoxy resin, 4-methylhexahydrophthalic anhydride curing agent and boron catalyst |
| EP1418206B1 (de) * | 2002-10-19 | 2004-10-13 | LEUNA-Harze GmbH | Härtbare Epoxidharzzusammensetzung |
| US20040101689A1 (en) | 2002-11-26 | 2004-05-27 | Ludovic Valette | Hardener composition for epoxy resins |
| JP4895487B2 (ja) * | 2003-08-05 | 2012-03-14 | 一般財団法人川村理化学研究所 | 熱硬化性樹脂組成物及びその製造方法、成型物の製造方法 |
| CN103554184A (zh) | 2004-05-28 | 2014-02-05 | 陶氏环球技术有限责任公司 | 可用于制造无卤素抗引燃聚合物的含磷化合物 |
| KR100970020B1 (ko) * | 2005-09-27 | 2010-07-16 | 스미토모 베이클리트 컴퍼니 리미티드 | 잠복성 촉매의 제조 방법 및 에폭시 수지 조성물 |
| JP5502326B2 (ja) * | 2005-12-22 | 2014-05-28 | ダウ グローバル テクノロジーズ エルエルシー | 硬化性エポキシ樹脂組成物およびそれから作られた積層体 |
| RU2470954C2 (ru) * | 2007-06-11 | 2012-12-27 | Басф Се | Катализатор для отверждения эпоксидов |
| US9018321B2 (en) | 2007-07-26 | 2015-04-28 | Ajinomoto Co., Inc. | Resin composition |
| JP5144572B2 (ja) * | 2009-03-26 | 2013-02-13 | 太陽ホールディングス株式会社 | 熱硬化性樹脂組成物 |
| SG176923A1 (en) * | 2009-06-22 | 2012-01-30 | Dow Global Technologies Llc | Hardener composition for epoxy resins |
| CN102031082B (zh) * | 2010-12-10 | 2013-04-03 | 东华大学 | 苯并咪唑二胺固化型环氧胶粘剂及其制备方法 |
| EP2814802B1 (en) * | 2012-02-17 | 2020-12-16 | Huntsman Advanced Materials Americas LLC | Mixture of benzoxazine, epoxy and anhydride |
| DK2695903T3 (en) * | 2012-08-08 | 2019-01-14 | Siemens Ag | Process for modifying the rate of temperature change of an epoxy resin composition in a resin container in a casting process |
| DK2695727T3 (en) | 2012-08-08 | 2018-02-12 | Siemens Ag | Process for accelerating the curing process in resino overflow systems for use in casting processes and resino overflow containers |
| WO2015103427A1 (en) | 2013-12-31 | 2015-07-09 | Saint-Gobain Performance Plastics Corporation | Composites for protecting signal transmitters/receivers |
| US11550220B2 (en) | 2019-10-31 | 2023-01-10 | Taiwan Semiconductor Manufacturing Co., Ltd. | Negative tone photoresist for EUV lithography |
| CN113278251A (zh) * | 2021-04-26 | 2021-08-20 | 厦门理工学院 | 柔性线路板使用的环氧树脂及其制备方法、装置、计算机设备 |
| DE102024103231A1 (de) | 2024-02-06 | 2025-08-07 | Alzchem Trostberg Gmbh | Lagerstabile Epoxidharz-Zusammensetzung und dafür geeignete Härtersysteme |
| CN119285906B (zh) * | 2024-10-25 | 2025-10-14 | 厦门艾贝森电子有限公司 | 一种生物质阻燃环氧电子封装材料及其制备方法 |
| CN119661811A (zh) * | 2024-12-02 | 2025-03-21 | 江南大学 | 基于酸酐-叔胺动态离子对潜伏型促进剂及其制法和用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3732332A (en) † | 1970-10-16 | 1973-05-08 | Allied Chem | Production of low molecular weight polyanhydrides and epoxy compositions derived therefrom |
| US3997499A (en) * | 1974-08-29 | 1976-12-14 | Gulf Oil Corporation | Resin-forming homogeneous solutions of styrene, maleic anhydride and copolymers thereof |
| US4594291A (en) * | 1984-07-17 | 1986-06-10 | The Dow Chemical Company | Curable, partially advanced epoxy resins |
| JPS62207320A (ja) * | 1986-03-07 | 1987-09-11 | Hitachi Ltd | 熱硬化性樹脂組成物で封止してなる半導体装置 |
| US4873273A (en) * | 1986-03-20 | 1989-10-10 | James River-Norwalk, Inc. | Epoxide coating composition |
| JPH072829B2 (ja) † | 1987-11-04 | 1995-01-18 | 株式会社日立製作所 | 積層板 |
| ATE143986T1 (de) * | 1988-02-12 | 1996-10-15 | Dow Chemical Co | Verwendung eines katalysators für epoxyharz- zusammensetzungen |
| GB8824391D0 (en) * | 1988-10-18 | 1988-11-23 | Ciba Geigy Ag | Compositions |
| EP0458502B1 (en) † | 1990-05-21 | 2003-06-18 | Dow Global Technologies Inc. | Latent catalysts, cure-inhibited epoxy resin compositions and laminates prepared therefrom |
| ZA913801B (en) * | 1990-05-21 | 1993-01-27 | Dow Chemical Co | Latent catalysts,cure-inhibited epoxy resin compositions and laminates prepared therefrom |
| EP0729484B1 (en) † | 1993-11-02 | 2000-03-01 | The Dow Chemical Company | Cure inhibited epoxy resin compositions and laminates prepared from the compositions |
| CN1062874C (zh) † | 1994-09-08 | 2001-03-07 | 阿克佐诺贝尔公司 | 含有烯属不饱和酸酐和乙烯系化合物的共聚物的含烯丙基环氧树脂组合物 |
| GB9421405D0 (en) † | 1994-10-21 | 1994-12-07 | Dow Chemical Co | Low voc laminating formulations |
-
1998
- 1998-01-20 EP EP98903586A patent/EP0954553B2/en not_active Expired - Lifetime
- 1998-01-20 AT AT98903586T patent/ATE273348T1/de active
- 1998-01-20 CN CN98802989A patent/CN1129648C/zh not_active Expired - Lifetime
- 1998-01-20 WO PCT/US1998/001041 patent/WO1998031750A1/en not_active Ceased
- 1998-01-20 DE DE69825561T patent/DE69825561T3/de not_active Expired - Lifetime
- 1998-01-20 JP JP53464498A patent/JP4080546B2/ja not_active Expired - Lifetime
- 1998-01-20 KR KR1019997006593A patent/KR100569617B1/ko not_active Expired - Fee Related
- 1998-01-21 TW TW087100801A patent/TW503246B/zh not_active IP Right Cessation
- 1998-01-21 MY MYPI98000244A patent/MY128727A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI496834B (zh) * | 2009-11-06 | 2015-08-21 | Dow Global Technologies Llc | 用於電用層板之儲存穩定的環氧樹脂組成物 |
| TWI613250B (zh) * | 2011-05-02 | 2018-02-01 | 蘭科智慧保護有限責任公司 | 環氧樹脂中之硼酸三甲酯 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE69825561D1 (de) | 2004-09-16 |
| EP0954553B2 (en) | 2008-12-10 |
| MY128727A (en) | 2007-02-28 |
| CN1129648C (zh) | 2003-12-03 |
| KR20000070360A (ko) | 2000-11-25 |
| KR100569617B1 (ko) | 2006-04-11 |
| DE69825561T2 (de) | 2005-08-11 |
| WO1998031750A1 (en) | 1998-07-23 |
| CN1249772A (zh) | 2000-04-05 |
| JP2001508828A (ja) | 2001-07-03 |
| EP0954553A1 (en) | 1999-11-10 |
| HK1023586A1 (en) | 2000-09-15 |
| EP0954553B1 (en) | 2004-08-11 |
| DE69825561T3 (de) | 2009-07-09 |
| ATE273348T1 (de) | 2004-08-15 |
| JP4080546B2 (ja) | 2008-04-23 |
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