JP4080546B2 - エポキシ硬化系のための潜触媒 - Google Patents
エポキシ硬化系のための潜触媒 Download PDFInfo
- Publication number
- JP4080546B2 JP4080546B2 JP53464498A JP53464498A JP4080546B2 JP 4080546 B2 JP4080546 B2 JP 4080546B2 JP 53464498 A JP53464498 A JP 53464498A JP 53464498 A JP53464498 A JP 53464498A JP 4080546 B2 JP4080546 B2 JP 4080546B2
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- acid
- resin composition
- catalyst
- anhydride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000003054 catalyst Substances 0.000 title claims description 84
- 239000004593 Epoxy Substances 0.000 title description 10
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 153
- 239000000203 mixture Substances 0.000 claims abstract description 117
- 239000003822 epoxy resin Substances 0.000 claims abstract description 96
- 239000002904 solvent Substances 0.000 claims abstract description 58
- 239000003112 inhibitor Substances 0.000 claims abstract description 44
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229920001577 copolymer Polymers 0.000 claims abstract description 15
- -1 Lewis acid derivative of boron Chemical class 0.000 claims description 82
- 229920005989 resin Polymers 0.000 claims description 48
- 239000011347 resin Substances 0.000 claims description 48
- 239000002253 acid Substances 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 239000003431 cross linking reagent Substances 0.000 claims description 28
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 26
- 239000004327 boric acid Substances 0.000 claims description 25
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 24
- 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 23
- 230000000269 nucleophilic effect Effects 0.000 claims description 23
- 238000000576 coating method Methods 0.000 claims description 19
- 239000004970 Chain extender Substances 0.000 claims description 16
- 239000002841 Lewis acid Substances 0.000 claims description 16
- 239000011248 coating agent Substances 0.000 claims description 16
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 16
- 150000008064 anhydrides Chemical class 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 230000001588 bifunctional effect Effects 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 150000007524 organic acids Chemical class 0.000 claims description 10
- 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 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- 239000011159 matrix material Substances 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 150000003868 ammonium compounds Chemical class 0.000 claims description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 229940014800 succinic anhydride Drugs 0.000 claims description 2
- 239000011975 tartaric acid Chemical class 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 239000003733 fiber-reinforced composite Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- WEHZNZTWKUYVIY-UHFFFAOYSA-N 3-oxabicyclo[3.2.2]nona-1(7),5,8-triene-2,4-dione Chemical compound O=C1OC(=O)C2=CC=C1C=C2 WEHZNZTWKUYVIY-UHFFFAOYSA-N 0.000 claims 1
- 229920002732 Polyanhydride Chemical class 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 47
- 150000008065 acid anhydrides Chemical class 0.000 abstract description 13
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 abstract description 6
- 238000004132 cross linking Methods 0.000 abstract description 6
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 abstract description 6
- 239000004971 Cross linker Substances 0.000 description 36
- 238000001723 curing Methods 0.000 description 32
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 27
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
- 229930195733 hydrocarbon Natural products 0.000 description 24
- 150000002430 hydrocarbons Chemical class 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 21
- 238000000034 method Methods 0.000 description 19
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 18
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 16
- 150000001450 anions Chemical class 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 238000012545 processing Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 125000001931 aliphatic group Chemical class 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 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 11
- 239000000463 material Substances 0.000 description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 10
- 230000002787 reinforcement Effects 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 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
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 8
- 150000002460 imidazoles Chemical class 0.000 description 8
- 239000002798 polar solvent Substances 0.000 description 8
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 7
- 239000002131 composite material Substances 0.000 description 7
- 150000002118 epoxides Chemical group 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 150000007517 lewis acids Chemical class 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 229920003986 novolac Polymers 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical class OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 6
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 6
- 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 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 239000011342 resin composition Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 150000003512 tertiary amines Chemical class 0.000 description 6
- 239000002966 varnish Substances 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000012779 reinforcing material Substances 0.000 description 5
- 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 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 229910000085 borane Inorganic materials 0.000 description 4
- 150000001638 boron Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 125000000466 oxiranyl group Chemical group 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 3
- VOWWYDCFAISREI-UHFFFAOYSA-N Bisphenol AP Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=CC=C1 VOWWYDCFAISREI-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 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
- 150000002170 ethers Chemical class 0.000 description 3
- 229930195729 fatty acid Chemical class 0.000 description 3
- 239000000194 fatty acid Chemical class 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 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 3
- 150000002576 ketones Chemical class 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229920001568 phenolic resin Polymers 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- 150000004714 phosphonium salts Chemical class 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 238000011417 postcuring Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical class COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 2
- HJVAFZMYQQSPHF-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;boric acid Chemical compound OB(O)O.OCCN(CCO)CCO HJVAFZMYQQSPHF-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 2
- 0 C*C(N*C)=*C(C)=CC Chemical compound C*C(N*C)=*C(C)=CC 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- DFQPZDGUFQJANM-UHFFFAOYSA-M tetrabutylphosphanium;hydroxide Chemical compound [OH-].CCCC[P+](CCCC)(CCCC)CCCC DFQPZDGUFQJANM-UHFFFAOYSA-M 0.000 description 1
- CCIYPTIBRAUPLQ-UHFFFAOYSA-M tetrabutylphosphanium;iodide Chemical compound [I-].CCCC[P+](CCCC)(CCCC)CCCC CCIYPTIBRAUPLQ-UHFFFAOYSA-M 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- RVULURSSSBRJRF-UHFFFAOYSA-M tris(2-ethoxyethyl)-ethylazanium;hydroxide Chemical compound [OH-].CCOCC[N+](CC)(CCOCC)CCOCC RVULURSSSBRJRF-UHFFFAOYSA-M 0.000 description 1
- 239000008096 xylene Substances 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
- C08G59/40—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
- C08G59/02—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 (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3594897P | 1997-01-21 | 1997-01-21 | |
| GB9701294.2 | 1997-01-22 | ||
| GBGB9701294.2A GB9701294D0 (en) | 1997-01-22 | 1997-01-22 | Latent catalysts for epoxy curing systems |
| GB60/035,948 | 1997-01-22 | ||
| PCT/US1998/001041 WO1998031750A1 (en) | 1997-01-21 | 1998-01-20 | Latent catalysts for epoxy curing systems |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001508828A JP2001508828A (ja) | 2001-07-03 |
| JP2001508828A5 JP2001508828A5 (https=) | 2005-09-08 |
| JP4080546B2 true JP4080546B2 (ja) | 2008-04-23 |
Family
ID=26310844
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP53464498A Expired - Lifetime JP4080546B2 (ja) | 1997-01-21 | 1998-01-20 | エポキシ硬化系のための潜触媒 |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0954553B2 (https=) |
| JP (1) | JP4080546B2 (https=) |
| KR (1) | KR100569617B1 (https=) |
| CN (1) | CN1129648C (https=) |
| AT (1) | ATE273348T1 (https=) |
| DE (1) | DE69825561T3 (https=) |
| MY (1) | MY128727A (https=) |
| TW (1) | TW503246B (https=) |
| WO (1) | WO1998031750A1 (https=) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001042359A1 (en) * | 1999-12-13 | 2001-06-14 | Dow Global Technologies Inc. | Flame retardant phosphorus element-containing epoxy resin compositions |
| US6641923B2 (en) | 2001-07-31 | 2003-11-04 | Ppg Industries Ohio, Inc. | Weldable coating compositions having improved intercoat adhesion |
| US6617401B2 (en) * | 2001-08-23 | 2003-09-09 | General Electric Company | Composition comprising cycloaliphatic epoxy resin, 4-methylhexahydrophthalic anhydride curing agent and boron catalyst |
| US6617400B2 (en) * | 2001-08-23 | 2003-09-09 | General Electric Company | Composition of cycloaliphatic epoxy resin, anhydride curing agent and boron catalyst |
| DE50201326D1 (de) * | 2002-10-19 | 2004-11-18 | 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 |
| BRPI0510861A (pt) | 2004-05-28 | 2007-12-26 | Dow Global Technologies Inc | processo para preparar um composto contendo fósforo, processo para preparar uma composição contendo fósforo, processo para preparar um composto de resina epóxi contendo fósforo, processo para preparar uma composição de resina epóxi contendo fósforo , processo para preparar um composto contendo um anel de benzoxazina e fósforo, processo para preparar uma composição de resina contendo anel de benzoxazina e fósforo, processo para preparar um composto contendo grupo termolábil e fósforo, processo para preparar uma composição de resina termolábil contendo fósforo, composto contendo fósforo, composição contendo fósforo, composição de resina epóxi contendo fósforo, composição contendo fósforo, composto de resina epóxi contendo fósforo, composto contendo anel de benzoxazina e fósforo, composição de resina contendo anel de benzoxazina e fósforo, composto contendo grupo termolábil e fósforo, composição de resina termolábil contendo fósforo, produto obtenìvel, composição de resina epóxi resistente à chama, composto de epóxi, composição de resina epóxi resistente a chama, composição de cura resistente à ignição, pré-impregnado, laminado, placa de circuito, poliol, resina de poliuretano resistente à chama, composição termoplástica resistente à ignição, composição hìbrida termoplástica / termofixa resistente à ignição e composição de revestimento |
| CN101273076B (zh) * | 2005-09-27 | 2011-01-19 | 住友电木株式会社 | 潜伏性催化剂的制造方法和环氧树脂组合物 |
| BRPI0621083A2 (pt) * | 2005-12-22 | 2011-11-29 | Dow Global Technologies Inc | composição de resina epóxi curável contendo halogênio, artigo compósito reforçado com fibra, componente de circuito elétrico, processo para produzir um artigo revestido, pré- impregnado, laminado, placa de circuito impresso (pcb), processo para preparar um artigo revestido com resina, e artigo revestido com resina |
| WO2008152003A1 (de) * | 2007-06-11 | 2008-12-18 | Basf Se | Katalysator für die härtung von epoxiden |
| EP2698393B1 (en) * | 2007-07-26 | 2015-08-19 | 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 |
| US20120083564A1 (en) * | 2009-06-22 | 2012-04-05 | Dow Global Technologies Llc | Hardener composition for epoxy resins |
| CN106751517A (zh) * | 2009-11-06 | 2017-05-31 | 蓝立方知识产权有限责任公司 | 用于电层合体的存储稳定的环氧树脂组合物 |
| 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 |
| EP2705090A1 (en) * | 2011-05-02 | 2014-03-12 | Dow Global Technologies LLC | Trimethyl borate in epoxy resins |
| AU2013219821B2 (en) * | 2012-02-17 | 2017-05-04 | Huntsman Advanced Materials Americas Llc | Mixture of benzoxazine, epoxy and anhydride |
| EP2695727B1 (en) * | 2012-08-08 | 2017-12-06 | Siemens Aktiengesellschaft | Method of accelerating the curing process in resin overflow systems for the use in casting processes and resin overflow container |
| 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 |
| 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 |
| CN119661811B (zh) * | 2024-12-02 | 2026-03-27 | 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 |
Family Cites Families (13)
| 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 |
| AU618313B2 (en) * | 1988-02-12 | 1991-12-19 | Dow Chemical Company, The | Epoxy resin composition containing latent catalysts |
| GB8824391D0 (en) * | 1988-10-18 | 1988-11-23 | Ciba Geigy Ag | Compositions |
| ATE243227T1 (de) † | 1990-05-21 | 2003-07-15 | Dow Global Technologies Inc | Latente katalysatoren, härtungsinhibierte epoxyharzzusammensetzungen und daraus hergestellte laminate |
| ZA913801B (en) * | 1990-05-21 | 1993-01-27 | Dow Chemical Co | Latent catalysts,cure-inhibited epoxy resin compositions and laminates prepared therefrom |
| DE69423234T2 (de) † | 1993-11-02 | 2000-08-10 | The Dow Chemical Co., Midland | Härtungsinhibierte epoxidharzzusammensetzungen und daraus hergestellte laminate |
| DE69505410T2 (de) † | 1994-09-08 | 1999-05-20 | Akzo Nobel N.V., Arnheim/Arnhem | Allylgruppen enthaltende zusammensetzungen aus epoxyharz und dem copolymer eines ethylenisch ungesättigten anhydrids und einer vinylverbindung |
| 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 WO PCT/US1998/001041 patent/WO1998031750A1/en not_active Ceased
- 1998-01-20 JP JP53464498A patent/JP4080546B2/ja not_active Expired - Lifetime
- 1998-01-20 CN CN98802989A patent/CN1129648C/zh not_active Expired - Lifetime
- 1998-01-20 AT AT98903586T patent/ATE273348T1/de active
- 1998-01-20 DE DE69825561T patent/DE69825561T3/de 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
Also Published As
| Publication number | Publication date |
|---|---|
| CN1249772A (zh) | 2000-04-05 |
| EP0954553B1 (en) | 2004-08-11 |
| DE69825561D1 (de) | 2004-09-16 |
| DE69825561T3 (de) | 2009-07-09 |
| EP0954553B2 (en) | 2008-12-10 |
| TW503246B (en) | 2002-09-21 |
| KR100569617B1 (ko) | 2006-04-11 |
| HK1023586A1 (en) | 2000-09-15 |
| CN1129648C (zh) | 2003-12-03 |
| WO1998031750A1 (en) | 1998-07-23 |
| JP2001508828A (ja) | 2001-07-03 |
| EP0954553A1 (en) | 1999-11-10 |
| DE69825561T2 (de) | 2005-08-11 |
| KR20000070360A (ko) | 2000-11-25 |
| MY128727A (en) | 2007-02-28 |
| ATE273348T1 (de) | 2004-08-15 |
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