DE69926790T2 - Polyoxazolidon-klebstoffzusammensetzung hergestellt aus polyepoxiden und polyisocyanaten - Google Patents
Polyoxazolidon-klebstoffzusammensetzung hergestellt aus polyepoxiden und polyisocyanaten Download PDFInfo
- Publication number
- DE69926790T2 DE69926790T2 DE69926790T DE69926790T DE69926790T2 DE 69926790 T2 DE69926790 T2 DE 69926790T2 DE 69926790 T DE69926790 T DE 69926790T DE 69926790 T DE69926790 T DE 69926790T DE 69926790 T2 DE69926790 T2 DE 69926790T2
- Authority
- DE
- Germany
- Prior art keywords
- metal foil
- polyepoxide
- compound
- bis
- polyisocyanate
- 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
Links
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 69
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 44
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 44
- 239000000853 adhesive Substances 0.000 title claims abstract description 17
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 17
- 239000000203 mixture Substances 0.000 title claims description 65
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 239000004970 Chain extender Substances 0.000 claims abstract description 25
- 239000011342 resin composition Substances 0.000 claims abstract description 18
- 239000000376 reactant Substances 0.000 claims abstract description 13
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical group O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 8
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 6
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 6
- 229920005989 resin Polymers 0.000 claims description 75
- 239000011347 resin Substances 0.000 claims description 75
- 239000002184 metal Substances 0.000 claims description 38
- 229910052751 metal Inorganic materials 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 32
- 239000011888 foil Substances 0.000 claims description 30
- 239000003054 catalyst Substances 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 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 23
- 238000000576 coating method Methods 0.000 claims description 22
- 239000011248 coating agent Substances 0.000 claims description 18
- -1 oxazolidone ring Compound Chemical class 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 15
- 229920001187 thermosetting polymer Polymers 0.000 claims description 15
- 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 14
- 239000012948 isocyanate Substances 0.000 claims description 12
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 12
- 239000004971 Cross linker Substances 0.000 claims description 11
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 10
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 10
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 235000013824 polyphenols Nutrition 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 229940106691 bisphenol a Drugs 0.000 claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000004840 adhesive resin Substances 0.000 claims description 7
- 229920006223 adhesive resin Polymers 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 5
- 229920002732 Polyanhydride Polymers 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 229920005992 thermoplastic resin Polymers 0.000 claims description 5
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- VESRBMGDECAMNH-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]-2,3,5,6-tetramethylphenol Chemical compound CC1=C(C(=C(C(=C1O)C)C)C(C)(C)C1=CC=C(C=C1)O)C VESRBMGDECAMNH-UHFFFAOYSA-N 0.000 claims description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 4
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002313 adhesive film Substances 0.000 claims description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 4
- 150000008442 polyphenolic compounds Polymers 0.000 claims description 4
- 230000003014 reinforcing effect Effects 0.000 claims description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 3
- XSTITJMSUGCZDH-UHFFFAOYSA-N 4-(4-hydroxy-2,6-dimethylphenyl)-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1C1=C(C)C=C(O)C=C1C XSTITJMSUGCZDH-UHFFFAOYSA-N 0.000 claims description 3
- 239000005062 Polybutadiene Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 239000013522 chelant Substances 0.000 claims description 3
- XPXMKIXDFWLRAA-UHFFFAOYSA-N hydrazinide Chemical compound [NH-]N XPXMKIXDFWLRAA-UHFFFAOYSA-N 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- 229920002857 polybutadiene Polymers 0.000 claims description 3
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 claims description 2
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims description 2
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 2
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 claims description 2
- IWNXTBMAHABHAK-UHFFFAOYSA-N 3,5-dibromo-2,6-dimethyl-4-propylphenol Chemical compound CCCC1=C(Br)C(C)=C(O)C(C)=C1Br IWNXTBMAHABHAK-UHFFFAOYSA-N 0.000 claims description 2
- KPOXQAKDFUYNFA-UHFFFAOYSA-N 3-methyl-7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound C1C(C(O)=O)C(C)CC2OC21 KPOXQAKDFUYNFA-UHFFFAOYSA-N 0.000 claims description 2
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 claims description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims description 2
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims description 2
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 2
- 150000002924 oxiranes Chemical group 0.000 claims 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- IJJYDUDCPUNWPJ-UHFFFAOYSA-N 2-methyl-1h-imidazole;2-phenyl-1h-imidazole Chemical compound CC1=NC=CN1.C1=CNC(C=2C=CC=CC=2)=N1 IJJYDUDCPUNWPJ-UHFFFAOYSA-N 0.000 claims 1
- XFUOBHWPTSIEOV-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohexane-1,2-dicarboxylate Chemical compound C1CCCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 XFUOBHWPTSIEOV-UHFFFAOYSA-N 0.000 claims 1
- 150000004714 phosphonium salts Chemical group 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 41
- 239000011889 copper foil Substances 0.000 abstract description 30
- 125000003700 epoxy group Chemical group 0.000 abstract description 2
- 238000009472 formulation Methods 0.000 description 30
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- 239000000463 material Substances 0.000 description 18
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000010408 film Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 12
- 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 11
- 239000010949 copper Substances 0.000 description 11
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- 239000008199 coating composition Substances 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
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- 150000002118 epoxides Chemical class 0.000 description 6
- 238000003475 lamination Methods 0.000 description 6
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- 230000008014 freezing Effects 0.000 description 5
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- 239000004848 polyfunctional curative Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- 230000000052 comparative effect Effects 0.000 description 4
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- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 3
- 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 3
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- 125000003277 amino group Chemical group 0.000 description 2
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 2
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- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical group N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
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- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- QDCPNGVVOWVKJG-VAWYXSNFSA-N 2-[(e)-dodec-1-enyl]butanedioic acid Chemical compound CCCCCCCCCC\C=C\C(C(O)=O)CC(O)=O QDCPNGVVOWVKJG-VAWYXSNFSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- QUQFTIVBFKLPCL-UHFFFAOYSA-L copper;2-amino-3-[(2-amino-2-carboxylatoethyl)disulfanyl]propanoate Chemical compound [Cu+2].[O-]C(=O)C(N)CSSCC(N)C([O-])=O QUQFTIVBFKLPCL-UHFFFAOYSA-L 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000000866 electrolytic etching Methods 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 238000007590 electrostatic spraying Methods 0.000 description 1
- 230000003028 elevating effect Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000007789 gas Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000001749 primary amide group Chemical group 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000012970 tertiary amine catalyst Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000004804 winding 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/003—Polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/302—Polyurethanes or polythiourethanes; Polyurea or polythiourea
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/38—Improvement of the adhesion between the insulating substrate and the metal
- H05K3/386—Improvement of the adhesion between the insulating substrate and the metal by the use of an organic polymeric bonding layer, e.g. adhesive
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/03—Conductive materials
- H05K2201/0332—Structure of the conductor
- H05K2201/0335—Layered conductors or foils
- H05K2201/0355—Metal foils
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/901—Printed circuit
-
- 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
-
- 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
- Y10T428/31515—As intermediate layer
-
- 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
- Y10T428/31515—As intermediate layer
- Y10T428/31522—Next to metal
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Manufacturing & Machinery (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Epoxy Resins (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Laminated Bodies (AREA)
- Adhesive Tapes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9827367 | 1998-12-11 | ||
| GBGB9827367.5A GB9827367D0 (en) | 1998-12-11 | 1998-12-11 | Adhesive resin composition |
| PCT/US1999/029431 WO2000034351A1 (en) | 1998-12-11 | 1999-12-10 | Polyoxazolidone adhesive resin composition prepared from polyepoxides and polyisocyanates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69926790D1 DE69926790D1 (de) | 2005-09-22 |
| DE69926790T2 true DE69926790T2 (de) | 2006-06-08 |
Family
ID=10844100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69926790T Expired - Lifetime DE69926790T2 (de) | 1998-12-11 | 1999-12-10 | Polyoxazolidon-klebstoffzusammensetzung hergestellt aus polyepoxiden und polyisocyanaten |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6432541B1 (enExample) |
| EP (1) | EP1137683B1 (enExample) |
| JP (2) | JP5209155B2 (enExample) |
| CN (1) | CN100379781C (enExample) |
| AT (1) | ATE302221T1 (enExample) |
| AU (1) | AU2051200A (enExample) |
| DE (1) | DE69926790T2 (enExample) |
| GB (1) | GB9827367D0 (enExample) |
| HK (1) | HK1043138B (enExample) |
| TW (1) | TWI240745B (enExample) |
| WO (1) | WO2000034351A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000294922A (ja) * | 1999-04-01 | 2000-10-20 | Victor Co Of Japan Ltd | 多層プリント配線板用の絶縁樹脂組成物 |
| JP3711842B2 (ja) * | 2000-06-01 | 2005-11-02 | ソニーケミカル株式会社 | 異方性導電接続材料及び接続構造体 |
| TW593404B (en) * | 2001-03-14 | 2004-06-21 | Akzo Nobel Nv | Powder coated rotor, stator or field coil and powder coating composition |
| US7431981B2 (en) * | 2002-11-04 | 2008-10-07 | The Boeing Company | Polymer composite structure reinforced with shape memory alloy and method of manufacturing same |
| US6989197B2 (en) * | 2002-11-04 | 2006-01-24 | The Boeing Company | Polymer composite structure reinforced with shape memory alloy and method of manufacturing same |
| KR100856186B1 (ko) * | 2005-04-07 | 2008-09-03 | 아사히 가세이 케미칼즈 가부시키가이샤 | 에폭시 수지 조성물 |
| EP1818044A1 (en) | 2005-11-25 | 2007-08-15 | DSMIP Assets B.V. | Cosmetic or personal care composition comprising a polymer comprising oxazolidon groups |
| EP2070963B1 (en) * | 2006-09-14 | 2013-04-03 | Panasonic Corporation | Epoxy resin composition for printed wiring board, resin composition varnish, prepreg, metal clad laminate, printed wiring board and multilayer printed wiring board |
| EP2148894B1 (en) * | 2007-05-16 | 2012-02-29 | Dow Global Technologies LLC | Flame retardant composition |
| JP2010540754A (ja) * | 2007-10-05 | 2010-12-24 | ダウ グローバル テクノロジーズ インコーポレイティド | イソシアネート変性エポキシ樹脂及びそのエポキシ粉体コーティング組成物 |
| US20100240816A1 (en) * | 2007-10-26 | 2010-09-23 | Dow Global Technologies Inc. | Epoxy resin composition containing isocyanurates for use in electrical laminates |
| WO2009070488A1 (en) * | 2007-11-29 | 2009-06-04 | Dow Global Technologies Inc. | Dimethylformamide-free formulations using dicyanadiamide as curing agent for thermosetting epoxy resins |
| US8742018B2 (en) * | 2008-01-08 | 2014-06-03 | Dow Global Technologies Llc | High Tg epoxy systems for composite applications |
| EP2268697B1 (en) * | 2008-04-14 | 2014-01-29 | Dow Global Technologies LLC | Epoxy-imidazole catalysts useful for powder coating applications |
| KR20110119634A (ko) * | 2009-01-06 | 2011-11-02 | 다우 글로벌 테크놀로지스 엘엘씨 | 에폭시 수지용 금속 안정화제 및 개선 방법 |
| CN102666633B (zh) * | 2009-11-12 | 2016-02-17 | 陶氏环球技术有限责任公司 | 聚噁唑烷酮树脂 |
| US20120129414A1 (en) * | 2010-11-24 | 2012-05-24 | Chung-Hao Chang | Thermosetting resin composition and prepreg or laminate using the same |
| US9408296B2 (en) | 2010-12-28 | 2016-08-02 | Mitsui Chemicals Tohcello, Inc. | Resin composition, and protective film, dry film, circuit board, and multilayer circuit board containing same |
| US20140121299A1 (en) * | 2011-07-04 | 2014-05-01 | Dow Global Technologies Llc | Adducts as tougheners in thermosettable epoxy systems |
| TWI444132B (zh) * | 2011-12-08 | 2014-07-01 | Ind Tech Res Inst | 電磁波屏蔽複合膜及具有該複合膜之軟性印刷電路板 |
| RU2618745C2 (ru) | 2012-11-07 | 2017-05-11 | ДАУ ГЛОБАЛ ТЕКНОЛОДЖИЗ ЭлЭлСи | Отверждаемая эпоксидная композиция и композит, полученный из нее |
| EP2803684A1 (de) * | 2013-05-13 | 2014-11-19 | Basf Se | Isocyanat-Epoxid-Hybridharze |
| CN103436155B (zh) * | 2013-09-09 | 2015-12-23 | 段宝荣 | 一种耐光性水性聚氨酯涂料的制备方法 |
| DE102014226842A1 (de) | 2014-12-22 | 2016-06-23 | Henkel Ag & Co. Kgaa | Katalysator-Zusammensetzung zur Härtung von Epoxidgruppen-haltigen Harzen |
| DE102014226838A1 (de) | 2014-12-22 | 2016-06-23 | Henkel Ag & Co. Kgaa | Oxazolidinon- und Isocyanurat-vernetzte Matrix für faserverstärktes Material |
| JP2016094610A (ja) * | 2015-11-24 | 2016-05-26 | ブルー キューブ アイピー エルエルシー | 熱硬化性エポキシ系の強化剤用付加体 |
| CN105295041B (zh) * | 2015-12-03 | 2017-07-25 | 苏州太湖电工新材料股份有限公司 | 一种聚噁唑烷酮树脂、其制备方法及在浸渍漆中的应用 |
| CN106916282B (zh) | 2015-12-28 | 2019-07-26 | 广东生益科技股份有限公司 | 一种环氧树脂组合物以及使用其的预浸料和层压板 |
| CN107227001B (zh) | 2016-03-25 | 2019-06-14 | 广东生益科技股份有限公司 | 一种无卤热固性树脂组合物以及含有它的预浸料、层压板和印制电路板 |
| EP3260481B1 (de) * | 2016-06-20 | 2022-02-23 | Henkel AG & Co. KGaA | Gehärtete zusammensetzung mit hoher schlagfestigkeit und temperaturbeständigkeit, basierend auf einem epoxidharz und einem polyisocyanat |
| JP6294927B1 (ja) | 2016-09-15 | 2018-03-14 | 日清紡ホールディングス株式会社 | 樹脂組成物及びこれを用いた熱伝導性軟質シート、並びに放熱構造 |
| CN106497024A (zh) * | 2016-10-27 | 2017-03-15 | 国家康复辅具研究中心 | 一种抗菌聚氨酯复合材料及其制备方法和应用 |
| WO2018149844A1 (de) * | 2017-02-16 | 2018-08-23 | Basf Se | Polyoxazolidone und deren herstellung |
| JP7323265B2 (ja) * | 2017-03-31 | 2023-08-08 | 富士紡ホールディングス株式会社 | 研磨パッド |
| EP3428045A1 (de) * | 2017-07-13 | 2019-01-16 | Sika Technology Ag | Einkomponentiger hitzehärtender epoxidklebstoff hoher auswaschbeständigkeit |
| EP3456754A1 (en) * | 2017-09-15 | 2019-03-20 | Covestro Deutschland AG | Method for the production of thermoplastic polyoxazolidinone polymers |
| JP7365096B2 (ja) * | 2017-09-29 | 2023-10-19 | ビーエーエスエフ ソシエタス・ヨーロピア | ジイソシアネートおよび２－フェニル－１，３－プロパンジオールのジグリシジルエーテル誘導体からの熱可塑性ポリオキサゾリドン |
| CN107652937B (zh) * | 2017-11-06 | 2021-03-30 | 烟台德邦科技股份有限公司 | 一种可与低表面能材料粘接的聚氨酯热熔胶的制备方法 |
| CN108371948A (zh) * | 2018-02-09 | 2018-08-07 | 安徽师范大学 | 新型亲和嗜硫硅球色谱材料及其制备方法和应用 |
| WO2019211127A1 (en) * | 2018-04-30 | 2019-11-07 | Evonik Degussa Gmbh | Polyurea compositions from polyaspartic esters and secondary heterocyclic amines derived aspartic esters |
| WO2020016276A1 (de) * | 2018-07-18 | 2020-01-23 | Basf Se | Bulkpolymerisierung von polyoxazolidon |
| EP3647335A1 (en) * | 2018-10-30 | 2020-05-06 | Covestro Deutschland AG | Method for the production of thermoplastic polyoxazolidinone polymers |
| US20220154055A1 (en) * | 2019-05-15 | 2022-05-19 | Dow Global Technologies Llc | Two-component adhesive compositions, articles prepared with same and preparation methods thereof |
| CN112175168B (zh) * | 2020-10-14 | 2021-12-14 | 上海交通大学 | 一种三元共聚物、嵌段聚合物以及三元共聚物的合成方法 |
| CN119019639A (zh) * | 2024-09-14 | 2024-11-26 | 万华化学集团股份有限公司 | 一种低内生热的热塑性聚氨酯弹性体及其制备方法和应用 |
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-
1998
- 1998-12-11 GB GBGB9827367.5A patent/GB9827367D0/en not_active Ceased
-
1999
- 1999-12-10 TW TW088121687A patent/TWI240745B/zh not_active IP Right Cessation
- 1999-12-10 AU AU20512/00A patent/AU2051200A/en not_active Abandoned
- 1999-12-10 JP JP2000586792A patent/JP5209155B2/ja not_active Expired - Fee Related
- 1999-12-10 WO PCT/US1999/029431 patent/WO2000034351A1/en not_active Ceased
- 1999-12-10 CN CNB998157384A patent/CN100379781C/zh not_active Expired - Fee Related
- 1999-12-10 US US09/458,379 patent/US6432541B1/en not_active Expired - Lifetime
- 1999-12-10 EP EP99964227A patent/EP1137683B1/en not_active Expired - Lifetime
- 1999-12-10 HK HK02102373.1A patent/HK1043138B/en not_active IP Right Cessation
- 1999-12-10 DE DE69926790T patent/DE69926790T2/de not_active Expired - Lifetime
- 1999-12-10 AT AT99964227T patent/ATE302221T1/de active
-
2012
- 2012-08-24 JP JP2012185696A patent/JP5735467B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP5735467B2 (ja) | 2015-06-17 |
| HK1043138A1 (en) | 2002-09-06 |
| TWI240745B (en) | 2005-10-01 |
| DE69926790D1 (de) | 2005-09-22 |
| JP2012251161A (ja) | 2012-12-20 |
| JP2003522217A (ja) | 2003-07-22 |
| EP1137683B1 (en) | 2005-08-17 |
| GB9827367D0 (en) | 1999-02-03 |
| ATE302221T1 (de) | 2005-09-15 |
| CN1333791A (zh) | 2002-01-30 |
| CN100379781C (zh) | 2008-04-09 |
| US6432541B1 (en) | 2002-08-13 |
| HK1043138B (en) | 2006-04-07 |
| AU2051200A (en) | 2000-06-26 |
| WO2000034351A1 (en) | 2000-06-15 |
| JP5209155B2 (ja) | 2013-06-12 |
| EP1137683A1 (en) | 2001-10-04 |
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