WO2004090010A1 - Uv硬化型液状ポリウレタン樹脂の製造法 - Google Patents
Uv硬化型液状ポリウレタン樹脂の製造法 Download PDFInfo
- Publication number
- WO2004090010A1 WO2004090010A1 PCT/JP2004/004986 JP2004004986W WO2004090010A1 WO 2004090010 A1 WO2004090010 A1 WO 2004090010A1 JP 2004004986 W JP2004004986 W JP 2004004986W WO 2004090010 A1 WO2004090010 A1 WO 2004090010A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- curable liquid
- polyurethane resin
- meth
- liquid polyurethane
- component
- Prior art date
Links
- 239000007788 liquid Substances 0.000 title claims abstract description 51
- 229920005749 polyurethane resin Polymers 0.000 title claims abstract description 45
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 15
- 230000008569 process Effects 0.000 title claims abstract description 10
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 41
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 30
- -1 alkylene glycol Chemical compound 0.000 claims abstract description 24
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 16
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000011248 coating agent Substances 0.000 claims abstract description 11
- 238000000576 coating method Methods 0.000 claims abstract description 11
- 239000003999 initiator Substances 0.000 claims abstract description 10
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 10
- 239000004417 polycarbonate Substances 0.000 claims abstract description 10
- 150000002009 diols Chemical class 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 5
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 claims description 5
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
- 239000012778 molding material Substances 0.000 claims description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 2
- 229940035437 1,3-propanediol Drugs 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000002355 alkine group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract description 6
- 238000007789 sealing Methods 0.000 abstract description 5
- 230000000052 comparative effect Effects 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000006835 compression Effects 0.000 description 5
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- 239000003085 diluting agent Substances 0.000 description 5
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- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 3
- 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 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- VLVZXTNDRFWYLF-UHFFFAOYSA-N [2-ethyl-2-(prop-2-enoyloxymethyl)hexyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CC)(CCCC)COC(=O)C=C VLVZXTNDRFWYLF-UHFFFAOYSA-N 0.000 description 3
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 3
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- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- WPMYUUITDBHVQZ-UHFFFAOYSA-M 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=CC(CCC([O-])=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-M 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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- 229920000570 polyether Polymers 0.000 description 2
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- 230000009257 reactivity Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- OJNQMAQBUFVVRJ-UHFFFAOYSA-N (2-ethyl-3-prop-2-enoyloxyheptyl) prop-2-enoate Chemical compound C(C=C)(=O)OC(C(COC(C=C)=O)CC)CCCC OJNQMAQBUFVVRJ-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-M 2-ethylacrylate Chemical compound CCC(=C)C([O-])=O WROUWQQRXUBECT-UHFFFAOYSA-M 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- ODWASQWJJUOKNN-UHFFFAOYSA-N 2-phenoxyprop-2-enoic acid Chemical compound OC(=O)C(=C)OC1=CC=CC=C1 ODWASQWJJUOKNN-UHFFFAOYSA-N 0.000 description 1
- 241000270722 Crocodylidae Species 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- WWEXBGFSEVKZNE-UHFFFAOYSA-N N=C=O.N=C=O.C1=CC=CC2=CC=CC=C21 Chemical class N=C=O.N=C=O.C1=CC=CC2=CC=CC=C21 WWEXBGFSEVKZNE-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000001458 anti-acid effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 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
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- MYWGVEGHKGKUMM-UHFFFAOYSA-N carbonic acid;ethene Chemical compound C=C.C=C.OC(O)=O MYWGVEGHKGKUMM-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- LNNWVNGFPYWNQE-GMIGKAJZSA-N desomorphine Chemical compound C1C2=CC=C(O)C3=C2[C@]24CCN(C)[C@H]1[C@@H]2CCC[C@@H]4O3 LNNWVNGFPYWNQE-GMIGKAJZSA-N 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
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- 238000011156 evaluation Methods 0.000 description 1
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- 239000011521 glass Substances 0.000 description 1
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- 235000019382 gum benzoic Nutrition 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 229940100573 methylpropanediol Drugs 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- MBAUOPQYSQVYJV-UHFFFAOYSA-N octyl 3-[4-hydroxy-3,5-di(propan-2-yl)phenyl]propanoate Chemical compound OC1=C(C=C(C=C1C(C)C)CCC(=O)OCCCCCCCC)C(C)C MBAUOPQYSQVYJV-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
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- 238000006116 polymerization reaction Methods 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
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- 229910052724 xenon Inorganic materials 0.000 description 1
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Classifications
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04N—PICTORIAL COMMUNICATION, e.g. TELEVISION
- H04N5/00—Details of television systems
- H04N5/76—Television signal recording
- H04N5/78—Television signal recording using magnetic recording
- H04N5/782—Television signal recording using magnetic recording on tape
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/067—Polyurethanes; Polyureas
-
- 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
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04N—PICTORIAL COMMUNICATION, e.g. TELEVISION
- H04N21/00—Selective content distribution, e.g. interactive television or video on demand [VOD]
- H04N21/20—Servers specifically adapted for the distribution of content, e.g. VOD servers; Operations thereof
- H04N21/23—Processing of content or additional data; Elementary server operations; Server middleware
- H04N21/235—Processing of additional data, e.g. scrambling of additional data or processing content descriptors
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04N—PICTORIAL COMMUNICATION, e.g. TELEVISION
- H04N21/00—Selective content distribution, e.g. interactive television or video on demand [VOD]
- H04N21/40—Client devices specifically adapted for the reception of or interaction with content, e.g. set-top-box [STB]; Operations thereof
- H04N21/41—Structure of client; Structure of client peripherals
- H04N21/414—Specialised client platforms, e.g. receiver in car or embedded in a mobile appliance
- H04N21/4147—PVR [Personal Video Recorder]
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04N—PICTORIAL COMMUNICATION, e.g. TELEVISION
- H04N21/00—Selective content distribution, e.g. interactive television or video on demand [VOD]
- H04N21/40—Client devices specifically adapted for the reception of or interaction with content, e.g. set-top-box [STB]; Operations thereof
- H04N21/43—Processing of content or additional data, e.g. demultiplexing additional data from a digital video stream; Elementary client operations, e.g. monitoring of home network or synchronising decoder's clock; Client middleware
- H04N21/435—Processing of additional data, e.g. decrypting of additional data, reconstructing software from modules extracted from the transport stream
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04N—PICTORIAL COMMUNICATION, e.g. TELEVISION
- H04N21/00—Selective content distribution, e.g. interactive television or video on demand [VOD]
- H04N21/40—Client devices specifically adapted for the reception of or interaction with content, e.g. set-top-box [STB]; Operations thereof
- H04N21/43—Processing of content or additional data, e.g. demultiplexing additional data from a digital video stream; Elementary client operations, e.g. monitoring of home network or synchronising decoder's clock; Client middleware
- H04N21/438—Interfacing the downstream path of the transmission network originating from a server, e.g. retrieving encoded video stream packets from an IP network
- H04N21/4383—Accessing a communication channel
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04N—PICTORIAL COMMUNICATION, e.g. TELEVISION
- H04N21/00—Selective content distribution, e.g. interactive television or video on demand [VOD]
- H04N21/40—Client devices specifically adapted for the reception of or interaction with content, e.g. set-top-box [STB]; Operations thereof
- H04N21/45—Management operations performed by the client for facilitating the reception of or the interaction with the content or administrating data related to the end-user or to the client device itself, e.g. learning user preferences for recommending movies, resolving scheduling conflicts
- H04N21/462—Content or additional data management, e.g. creating a master electronic program guide from data received from the Internet and a Head-end, controlling the complexity of a video stream by scaling the resolution or bit-rate based on the client capabilities
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04N—PICTORIAL COMMUNICATION, e.g. TELEVISION
- H04N7/00—Television systems
- H04N7/08—Systems for the simultaneous or sequential transmission of more than one television signal, e.g. additional information signals, the signals occupying wholly or partially the same frequency band, e.g. by time division
- H04N7/087—Systems for the simultaneous or sequential transmission of more than one television signal, e.g. additional information signals, the signals occupying wholly or partially the same frequency band, e.g. by time division with signal insertion during the vertical blanking interval only
- H04N7/088—Systems for the simultaneous or sequential transmission of more than one television signal, e.g. additional information signals, the signals occupying wholly or partially the same frequency band, e.g. by time division with signal insertion during the vertical blanking interval only the inserted signal being digital
- H04N7/0887—Systems for the simultaneous or sequential transmission of more than one television signal, e.g. additional information signals, the signals occupying wholly or partially the same frequency band, e.g. by time division with signal insertion during the vertical blanking interval only the inserted signal being digital for the transmission of programme or channel identifying signals
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04N—PICTORIAL COMMUNICATION, e.g. TELEVISION
- H04N21/00—Selective content distribution, e.g. interactive television or video on demand [VOD]
- H04N21/40—Client devices specifically adapted for the reception of or interaction with content, e.g. set-top-box [STB]; Operations thereof
- H04N21/47—End-user applications
- H04N21/472—End-user interface for requesting content, additional data or services; End-user interface for interacting with content, e.g. for content reservation or setting reminders, for requesting event notification, for manipulating displayed content
- H04N21/47214—End-user interface for requesting content, additional data or services; End-user interface for interacting with content, e.g. for content reservation or setting reminders, for requesting event notification, for manipulating displayed content for content reservation or setting reminders; for requesting event notification, e.g. of sport results or stock market
Definitions
- the present invention relates to a method for producing a UV-curable liquid polyurethane resin. More particularly, the present invention relates to a method for producing a UV-curable liquid polyurethane resin which is applicable to an automatic robot and which can be suitably used as a molding material for a light HDD gasket or the like.
- An object of the present invention is to provide a method for producing a UV-curable liquid polyurethane resin capable of efficiently producing a gasket or the like for an HDD having a cross-sectional shape having a high sealing property by an automatic coating robot.
- (G) a photopolymerization initiator and (H) a hindered phenol based antioxidant having a molecular weight of 500 to 2000 are added before or after the terminal (meth) atalylation reaction of the urethane oligomer.
- a curable liquid polyurethane resin is formed.
- (meth) atalylate means atalylate or meta tarylate, which does not prevent the use of both of them.
- the components (A), (B) and (C) are reacted in the presence of the components (D) and (E) to prepare a (meth) acrylate solution of a urethane oligomer.
- the preparation of is first carried out.
- component (B) one having a molecular weight of 100 to 2,000, preferably 122 to 1,000, is used, for example, a general formula
- other alkylene oxide adducts of trimethylolpropane with ethylene oxide, etc. can also be used. If trifunctional alcohol is not used, as shown in the results of Comparative Example 1 below, the gasket processability (the liquid after coating and the adhesion after curing) and the compression set resistance become inferior. .
- diisocyanate compound of component (C) there are 4, -diphenylmethane diisocyanate (MDI), polymeric MDI, tolylene diisocyanate, and trie
- MDI -diphenylmethane diisocyanate
- polymeric MDI polymeric MDI
- tolylene diisocyanate polymeric MDI
- trie Aromatic diisocyanates
- diisocyanates diisocyanates, tolidine diisocyanates, p-phenylidene diisocyanates, naphthalene diisocyanates and the like are preferably used.
- aliphatic diisocyanates is not suitable as a diisocyanate compound because the reactivity is lower than aromatic diisocyanates and tends to remain as unreacted components.
- component (A),), and (C) form urethane oligomers, and therefore about 0.5 to 10 parts by weight of component (B) per 100 parts by weight of component (A), preferably about 1 to 8
- component (C) is about 20 to 60 parts by weight, preferably about 25 to 50 parts by weight, and the NC0 / 0H equivalent ratio is 1.01 to 2.00, preferably 1.05 to 1. It is used at an equivalence ratio of 12.
- the reaction is preferably carried out in the coexistence of the (D) component and the (E) component.
- Examples of the (meth) acrylate compound of the component (D) include methyl acrylate, benzyl acrylate, n-butyl acrylate, 2-ethyl acrylate, n-acetyl acrylate, 2-ethoxy ethyl atarylate.
- 2-Phenyloxyethyl atalylate or metatalylate corresponding thereto is preferably used, preferably 2-ethylhexyl atalylate.
- (Meth) atarilate is also used. These (meth) atalylate compounds function as a solvent for the water-oligomerization reaction, as well as lowering the glass transition temperature of the cured product and reducing the polarity (hydrophilicity).
- the component (D) is used in a proportion of about 10 to 200 parts by weight, preferably about 20 to 100 parts by weight, per 100 parts by weight of the component (A).
- the component (E) not only functions as a solvent for the oligomerization reaction, but also improves the curing reactivity and the properties of the UV cured product upon UV irradiation, and if this is not used, the results of Comparative Example 6 will be described. As shown, tensile strength is reduced, compression resistance, permanent set characteristics are reduced, and adhesion after curing is observed.
- These components (E) are used in a proportion of about 1 to 20 parts by weight, preferably about 2 to 15 parts by weight, per 100 parts by weight of component (A).
- ethylene oxide di (meth) acrylates such as triethylene glycol di (meth) acrylate are not suitable for high humidity barrier applications because of their high polarity.
- the component (F) is added to the (meth) acrylate solution of the urethane oligomer obtained from each of these components, and the terminal (meth) acrylate reaction of the urethane oligomer by the component (F) is about 40 to 120 °. C, preferably at about 80-100 ° C.
- Examples of the hydroxyl group-containing (meth) atalylate of the component (F) include, for example, 2-hydroxylenoarylate, 2-hydroxylmethacrylate methacrylate, 2-hydroxypropylacrylate, etc. 400 hydroxyalkyl (meth) atarylates are commonly used.
- the hydroxyl group of the hydroxyl-containing (meth) atalylate is It is used to react with the terminal isocyanato group of the gomer to polyurethaneate the molecular chain end of the urethane oligomer and introduce a (meth) acrylate group thereto, and if it is not used, the result of Comparative Example 7 will be described later. As shown, UV cure is insufficient.
- the hydroxylated (meth) atalylate is used at a ratio such that the NC0 / 0H equivalent ratio is 0.10 to 0.90 with respect to the terminal isocyanate group in the generated urethane oligomer.
- photopolymerization initiator of the component (G) commonly used photopolymerization initiators such as benzoin alkyl ether type, acetophenone type, propiophenone type, anthraquinone type, thioxanthone type, etc., for example, 1-hydroxycyclohexyl Phenyl ketone, benzoin ether, benzyl dimethyl ketal, c-hydroxyalkylphenone, ⁇ -aminoalkylphenone, bisacylphosphine oxide, etc. 1 Urethane acrylate oligomer produced about 0.1 to 10 parts by weight per 100 parts by weight Used in parts by weight. In addition, it is possible to use a small amount of sensitizer as much as possible, if necessary.
- hindered phenol-based antioxidant of the ( ⁇ ) component for example, pentaerythrityl tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], 1, 6- Xandiol bis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], triethylene glycol bis [3- (3-tert-butyl-5-methyl-4-hydroxyphenyl) propionate Or the like, and if it has a molecular weight in such a range, commercially available products, such as Ciba ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ 10/80 Can be used as it is.
- the antioxidant itself is a gas generating component, and it is unsuitable for use in precision equipment parts such as HDD.
- those having a molecular weight of 2000 or more have poor solubility with liquid polyurethane resins and can not exert sufficient antioxidant effect.
- These anti-acid agents are used in an amount of about 0.1 to 10 parts by weight, preferably about 1 to 5 parts by weight, based on 100 parts by weight of the generated urethane acrylate oligomer. Used in proportions by volume.
- the photopolymerization initiator as the component (G) and the hindered phenolic acid inhibitor as the component (H) can be added before or after the terminal (meth) acrylate reaction of the urethane oligomer, or one of them Can be added before this reaction and the other after this reaction. However, since the viscosity becomes very high after the terminal (meth) atalylation reaction of the urethane oligomer, it is preferable to add it before the terminal (meth) acrylate reaction.
- the UV curable liquid polyurethane resin obtained as a result of the terminal (meth) acrylate reaction of the urethane oligomer has a viscosity (25 ° 0 of 150, 000 to 1,000, 00 (1 ⁇ 213 ′ ′ 3, preferably 17,000) The viscosity is adjusted to have a viscosity of 800 to 800,000 mPa's.
- the UV curable liquid polyurethane resin of the present invention thus exhibiting high viscosity is obtained by using an automatic coating robot, for example, an XY-Z axis coating robot, at a temperature of about 30 to 80 ° C., preferably 40 to 80 ° C.
- a curing reaction can be performed by ultraviolet (UV) irradiation, and then a high temperature treatment at about 100 to 180 ° C. can be performed to manufacture a gasket.
- UV light source xenon lamp, low pressure mercury lamp, high pressure mercury lamp, ultra high pressure mercury lamp and the like are used.
- the ultraviolet irradiation conditions depend on the irradiation apparatus used, but generally, the irradiation amount of about 1000 to 10000 mJ / cm 2 , the irradiation time of about 10 seconds to about 5 minutes The firing time is used.
- the ultraviolet irradiation is carried out in an atmosphere with a reduced oxygen concentration, such as an inert gas atmosphere or an atmosphere in air.
- Example 1 a UV curable liquid polyuretan resin B was obtained using 92.2 parts of phenyloxyacrylate in place of 2-ethylhexyl atalylate.
- Example 1 without using trimethylolpropane derivative, The amount of silacreate is 88.1 parts, the amount of 2-butyl-2-ethyl-1, 3-propanediolarylate is 4. 6 parts, and the amount of 4, 4'-diphenylmethane diisocyanate is 4. 26. Change to 3 parts each to obtain an urethane oligomer monoacrylate solution.
- urethane oligomer acrylate solution 8.2 parts of 2-hydroxy methacrylate, 2.3 parts of 1-hydroxycyclohexyl phenyl ketone, and a hindered phenol based antioxidant ( 2. 3 parts of Irganox 1010) was added, and terminal acrylate reaction of urethane oligomer was carried out at 80 to 100 ° C. for 60 minutes to obtain a UV-curable liquid polyurethane resin C.
- Example 1 the amount of 2-ethyl hexyl atalylate is changed to 44.3 parts, and the amount of 2-butyl-2-ethyl-1, 3-propanediol diacrylate is changed to 4.0 parts. An acrylate solution of tan oligomer was obtained.
- urethane oligomer acrylate thus obtained, 8.0 parts of 2-hydroxystyrene, acrylate 2.0 parts of 1-hydroxycyclohexyl / rephenone ketone and hindered phenol-based antioxidant are contained. (Irganox 1010) 2. 0 parts were added, and the terminal acrylate reaction of the urethane oligomer was carried out at 80 to 100 ° C. for 60 minutes to obtain a UV-curable liquid polyurethane resin D.
- Example 1 a UV-curable liquid polyurethane resin E was obtained without the addition of a hindered phenol-based antioxidant.
- Example 1 2.5 parts of a low molecular weight type phenol / phenol based antioxidant (CycloCity. Specialty Chemicals Inc. Irganox 1135; molecular weight about 400) is used, UV curable liquid polyurethane resin F I got
- Example 1 instead of polycarbonate monothiol, 3-methyl-1,5-penta A UV curable liquid polyurethane resin G was obtained using the same amount of a polyester polyol (Kuraray product Kuraray polyol P-1010; average molecular weight about 1000) derived from ndiol and adipic acid.
- a polyester polyol Kerpton product Kuraray polyol P-1010; average molecular weight about 1000
- a UV curable liquid polyurethane resin H was obtained without using 2-butyl-2-ethyl-1,3-propanediol diacrylate.
- a UV curable liquid polyurethane resin I was obtained without using 2-hydroxy ethyl acrylate.
- UV-curable liquid polyurethane resins A to A obtained in the above Examples and Comparative Examples are respectively poured into glass molds and then immediately irradiated with ultraviolet light at an irradiation dose of 8000 nJ cm 2 for 2 to 3 minutes, and then 150 High-temperature treatment at 7 ° C for 7 hours gave a sheet (thickness 2 ⁇ m) for evaluation of hardness, tensile properties, compression set, water absorption and generated gas amount.
- the discharge pressure is 100kPa
- the drawing speed is 40 ⁇ / sec while heating to 60 ° C.
- a linear body depicting a gasket-like locus is applied along the inner circumference of the outer circumference of a rectangular (70 x 100%) aluminum plate so as to form a cross-sectional mountain shape, and the irradiation dose is immediately 8000 m X
- a pseudogasket cover was obtained by sequentially performing UV irradiation at 15 seconds for cm 2 irradiation time and high temperature treatment for 7 hours at 150 ° C.
- the UV-curable liquid polyurethane resin according to the present invention can be applied to a metal plate or the like at a high temperature using an automatic coating robot to obtain a mountain-shaped one having a sufficient height in cross section. There is no dripping even in a high temperature environment in the curing process using a UV irradiation lamp, and it is possible to maintain a high cross-sectional peak shape immediately after application, and as a result, a high height / width ratio and a high cross section mountain More specifically, the width of the part in contact with the metal substrate is about 0.5 to 3.0 mm, the height from the metal substrate is about 0.5 to 2.0 mm, and the height / width ratio is about 0.5 to 2.0 This makes it possible to obtain gaskets with a cross-sectional mountain shape, in other words, gaskets with high sealability.
- LJV-curable liquid polyurethane resins having such a composition have a metal substrate having an oxide film due to the presence of an appropriate polar group possessed by a mono (meth) acreite having a specific structure which is a reactive diluent component.
- the gasket thus obtained exhibits low water absorptivity, high humidity moisture resistance, and excellent heat resistance due to its high degree of intermolecular cohesion with its polycarbonate structure, and it is particularly excellent in heat resistance.
- an antioxidant By adding an antioxidant, the heat resistance is further improved, and even if it is treated at high temperature, only unreacted low molecular weight components can be removed without thermal decomposition.
- the low acid gas gasket thus obtained is for HDD Suitable for use on precision instruments such as
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Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/552,236 US7531580B2 (en) | 2003-04-10 | 2004-04-07 | Process for production of uv-curable liquid polyurethane resin |
JP2005505296A JP3853351B2 (ja) | 2003-04-10 | 2004-04-07 | Uv硬化型液状ポリウレタン樹脂の製造法 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP2003-105981 | 2003-04-10 | ||
JP2003105981 | 2003-04-10 |
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WO2004090010A1 true WO2004090010A1 (ja) | 2004-10-21 |
Family
ID=33156897
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Application Number | Title | Priority Date | Filing Date |
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PCT/JP2004/004986 WO2004090010A1 (ja) | 2003-04-10 | 2004-04-07 | Uv硬化型液状ポリウレタン樹脂の製造法 |
Country Status (4)
Country | Link |
---|---|
US (1) | US7531580B2 (ja) |
JP (1) | JP3853351B2 (ja) |
CN (1) | CN100339411C (ja) |
WO (1) | WO2004090010A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100368455C (zh) * | 2006-03-22 | 2008-02-13 | 中国科学技术大学 | 一种可紫外光固化水性聚氨酯树脂的制备方法 |
CN100424145C (zh) * | 2006-05-15 | 2008-10-08 | 汕头大学 | 紫外光固化水性聚氨酯丙烯酸酯涂料树脂及其制备方法 |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5716881B2 (ja) * | 2008-10-04 | 2015-05-13 | スリーボンドファインケミカル株式会社 | 光硬化性接着剤組成物 |
JP6469341B2 (ja) * | 2013-09-25 | 2019-02-13 | 第一工業製薬株式会社 | 硬化性樹脂組成物及びそれを含有するコーティング用組成物。 |
JP6578660B2 (ja) * | 2015-01-22 | 2019-09-25 | 富士ゼロックス株式会社 | 三次元造形用支持材、三次元造形用組成物セット、および三次元造形装置、三次元造形物の製造方法 |
WO2019097975A1 (ja) | 2017-11-14 | 2019-05-23 | 本田技研工業株式会社 | シール材及びこれを備える振動減衰装置 |
CN109332115A (zh) * | 2018-08-02 | 2019-02-15 | 无锡金科涂装有限公司 | 一种压铸铝合金的表面浸渗方法 |
JP7387973B2 (ja) * | 2019-03-19 | 2023-11-29 | 本州化学工業株式会社 | 末端(メタ)アクリレートポリカーボネートオリゴマー |
CN115851082B (zh) * | 2022-12-02 | 2023-12-05 | 广东炎墨方案科技有限公司 | 一种高抗氧化的阻焊涂料及其制备方法 |
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JPS63165418A (ja) * | 1986-12-27 | 1988-07-08 | Toagosei Chem Ind Co Ltd | 接着剤組成物 |
JPH06145276A (ja) * | 1992-11-09 | 1994-05-24 | Toagosei Chem Ind Co Ltd | 光硬化型樹脂組成物 |
JPH0841147A (ja) * | 1994-07-27 | 1996-02-13 | Japan Synthetic Rubber Co Ltd | 光学的立体造形用樹脂組成物 |
JPH0892342A (ja) * | 1994-09-22 | 1996-04-09 | Japan Synthetic Rubber Co Ltd | 放射線硬化性樹脂組成物 |
WO1996010594A1 (fr) * | 1994-09-30 | 1996-04-11 | Zeon Rize Co., Ltd. | Composition de materiau pour joint etanche et procede de production d'un joint etanche a partir de cette composition |
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JP2001225392A (ja) | 2000-02-17 | 2001-08-21 | Nippon Mektron Ltd | 精密機器用ガスケットの製造方法 |
JP2003105320A (ja) | 2001-09-28 | 2003-04-09 | Nippon Mektron Ltd | 精密機器用液状ガスケット材料およびそれを用いた精密機器用ガスケットの製造方法 |
-
2004
- 2004-04-07 JP JP2005505296A patent/JP3853351B2/ja not_active Expired - Fee Related
- 2004-04-07 US US10/552,236 patent/US7531580B2/en not_active Expired - Fee Related
- 2004-04-07 WO PCT/JP2004/004986 patent/WO2004090010A1/ja active Application Filing
- 2004-04-07 CN CNB2004800096329A patent/CN100339411C/zh not_active Expired - Fee Related
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS63165418A (ja) * | 1986-12-27 | 1988-07-08 | Toagosei Chem Ind Co Ltd | 接着剤組成物 |
JPH06145276A (ja) * | 1992-11-09 | 1994-05-24 | Toagosei Chem Ind Co Ltd | 光硬化型樹脂組成物 |
JPH0841147A (ja) * | 1994-07-27 | 1996-02-13 | Japan Synthetic Rubber Co Ltd | 光学的立体造形用樹脂組成物 |
JPH0892342A (ja) * | 1994-09-22 | 1996-04-09 | Japan Synthetic Rubber Co Ltd | 放射線硬化性樹脂組成物 |
WO1996010594A1 (fr) * | 1994-09-30 | 1996-04-11 | Zeon Rize Co., Ltd. | Composition de materiau pour joint etanche et procede de production d'un joint etanche a partir de cette composition |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100368455C (zh) * | 2006-03-22 | 2008-02-13 | 中国科学技术大学 | 一种可紫外光固化水性聚氨酯树脂的制备方法 |
CN100424145C (zh) * | 2006-05-15 | 2008-10-08 | 汕头大学 | 紫外光固化水性聚氨酯丙烯酸酯涂料树脂及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN100339411C (zh) | 2007-09-26 |
US7531580B2 (en) | 2009-05-12 |
JP3853351B2 (ja) | 2006-12-06 |
CN1771273A (zh) | 2006-05-10 |
US20060194938A1 (en) | 2006-08-31 |
JPWO2004090010A1 (ja) | 2006-07-06 |
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