CA2603710A1 - Epoxy silane oligomer and coating composition containing same - Google Patents
Epoxy silane oligomer and coating composition containing same Download PDFInfo
- Publication number
- CA2603710A1 CA2603710A1 CA002603710A CA2603710A CA2603710A1 CA 2603710 A1 CA2603710 A1 CA 2603710A1 CA 002603710 A CA002603710 A CA 002603710A CA 2603710 A CA2603710 A CA 2603710A CA 2603710 A1 CA2603710 A1 CA 2603710A1
- Authority
- CA
- Canada
- Prior art keywords
- silane
- weight
- water
- eso
- surfactant
- 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.)
- Abandoned
Links
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 title claims abstract description 153
- 229910000077 silane Inorganic materials 0.000 title claims abstract description 153
- 239000004593 Epoxy Substances 0.000 title claims abstract description 120
- 239000008199 coating composition Substances 0.000 title claims description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 137
- 238000000034 method Methods 0.000 claims abstract description 86
- 230000008569 process Effects 0.000 claims abstract description 45
- -1 glycidoxy Chemical group 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- NWLSIXHRLQYIAE-UHFFFAOYSA-N oxiran-2-ylmethoxysilicon Chemical compound [Si]OCC1CO1 NWLSIXHRLQYIAE-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 239000004094 surface-active agent Substances 0.000 claims description 80
- 239000000178 monomer Substances 0.000 claims description 46
- 239000004615 ingredient Substances 0.000 claims description 43
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 40
- 229910052751 metal Inorganic materials 0.000 claims description 40
- 239000002184 metal Substances 0.000 claims description 40
- 239000004327 boric acid Substances 0.000 claims description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- 239000003002 pH adjusting agent Substances 0.000 claims description 19
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 18
- 239000006184 cosolvent Substances 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 9
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 9
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 6
- 239000004971 Cross linker Substances 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 claims description 6
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 claims description 6
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims description 6
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 5
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 5
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 5
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 claims description 4
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims description 4
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002736 nonionic surfactant Substances 0.000 claims description 4
- MSRJTTSHWYDFIU-UHFFFAOYSA-N octyltriethoxysilane Chemical compound CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 claims description 4
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 claims description 3
- OHJYHAOODFPJOD-UHFFFAOYSA-N 2-(2-ethylhexoxy)ethanol Chemical compound CCCCC(CC)COCCO OHJYHAOODFPJOD-UHFFFAOYSA-N 0.000 claims description 3
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 claims description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 3
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 claims description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 3
- UPGSWASWQBLSKZ-UHFFFAOYSA-N 2-hexoxyethanol Chemical compound CCCCCCOCCO UPGSWASWQBLSKZ-UHFFFAOYSA-N 0.000 claims description 3
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 3
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 claims description 3
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 claims description 3
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims description 3
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 239000003945 anionic surfactant Substances 0.000 claims description 3
- 239000003093 cationic surfactant Substances 0.000 claims description 3
- 239000000919 ceramic Substances 0.000 claims description 3
- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 claims description 3
- MABAWBWRUSBLKQ-UHFFFAOYSA-N ethenyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)C=C MABAWBWRUSBLKQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000012188 paraffin wax Substances 0.000 claims description 3
- 229960005323 phenoxyethanol Drugs 0.000 claims description 3
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 claims description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- FUWDFGKRNIDKAE-UHFFFAOYSA-N 1-butoxypropan-2-yl acetate Chemical compound CCCCOCC(C)OC(C)=O FUWDFGKRNIDKAE-UHFFFAOYSA-N 0.000 claims description 2
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 claims description 2
- CHPNMYQJQQGAJS-UHFFFAOYSA-N 3-tri(propan-2-yloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)CCCOC(=O)C(C)=C CHPNMYQJQQGAJS-UHFFFAOYSA-N 0.000 claims description 2
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002318 adhesion promoter Substances 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910021485 fumed silica Inorganic materials 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 2
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 claims description 2
- 229960003493 octyltriethoxysilane Drugs 0.000 claims 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 claims 1
- DJCYDDALXPHSHR-UHFFFAOYSA-N 2-(2-propoxyethoxy)ethanol Chemical compound CCCOCCOCCO DJCYDDALXPHSHR-UHFFFAOYSA-N 0.000 claims 1
- SAJBQPSHPCBOJI-UHFFFAOYSA-N 2-methyl-1-tri(propan-2-yloxy)silylprop-2-en-1-one Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)C(=O)C(C)=C SAJBQPSHPCBOJI-UHFFFAOYSA-N 0.000 claims 1
- BGSDLKLNXFWQGB-UHFFFAOYSA-N 2-methyl-1-triethoxysilylprop-2-en-1-one Chemical compound CCO[Si](OCC)(OCC)C(=O)C(C)=C BGSDLKLNXFWQGB-UHFFFAOYSA-N 0.000 claims 1
- IKTABEIWDPZBHF-UHFFFAOYSA-N 2-methyl-1-trimethoxysilylprop-2-en-1-one Chemical compound CO[Si](OC)(OC)C(=O)C(C)=C IKTABEIWDPZBHF-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
- 239000007822 coupling agent Substances 0.000 claims 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 claims 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 189
- 239000000203 mixture Substances 0.000 description 122
- 239000006185 dispersion Substances 0.000 description 114
- 238000000576 coating method Methods 0.000 description 103
- 239000011248 coating agent Substances 0.000 description 74
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 65
- 238000009472 formulation Methods 0.000 description 61
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 59
- 230000032683 aging Effects 0.000 description 59
- 229910052725 zinc Inorganic materials 0.000 description 55
- 239000011701 zinc Substances 0.000 description 55
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 50
- 229910052782 aluminium Inorganic materials 0.000 description 49
- 229920001296 polysiloxane Polymers 0.000 description 47
- 239000000047 product Substances 0.000 description 47
- 239000000243 solution Substances 0.000 description 47
- 235000010338 boric acid Nutrition 0.000 description 39
- 229960002645 boric acid Drugs 0.000 description 39
- 238000013019 agitation Methods 0.000 description 37
- 238000000227 grinding Methods 0.000 description 36
- 239000000758 substrate Substances 0.000 description 35
- 238000005260 corrosion Methods 0.000 description 33
- 230000007797 corrosion Effects 0.000 description 32
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 31
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 30
- WGYZMNBUZFHYRX-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-ol Chemical compound COCC(C)OCC(C)O WGYZMNBUZFHYRX-UHFFFAOYSA-N 0.000 description 28
- 239000000843 powder Substances 0.000 description 27
- 238000003756 stirring Methods 0.000 description 26
- 239000000126 substance Substances 0.000 description 26
- 239000003973 paint Substances 0.000 description 25
- 239000002562 thickening agent Substances 0.000 description 25
- 239000000049 pigment Substances 0.000 description 23
- 238000003860 storage Methods 0.000 description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 22
- 238000001723 curing Methods 0.000 description 21
- 239000001257 hydrogen Substances 0.000 description 21
- 229910052739 hydrogen Inorganic materials 0.000 description 21
- 239000000945 filler Substances 0.000 description 18
- PUMRUSBKNSBTAL-UHFFFAOYSA-N 3,4-dihydro-2h-chromene-2-carbaldehyde Chemical compound C1=CC=C2OC(C=O)CCC2=C1 PUMRUSBKNSBTAL-UHFFFAOYSA-N 0.000 description 17
- 239000004411 aluminium Substances 0.000 description 17
- 239000007921 spray Substances 0.000 description 17
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 16
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 15
- 239000012736 aqueous medium Substances 0.000 description 15
- 239000013528 metallic particle Substances 0.000 description 15
- 150000004756 silanes Chemical class 0.000 description 15
- 230000008878 coupling Effects 0.000 description 14
- 238000010168 coupling process Methods 0.000 description 14
- 238000005859 coupling reaction Methods 0.000 description 14
- 239000011253 protective coating Substances 0.000 description 14
- 239000000080 wetting agent Substances 0.000 description 14
- 229920005989 resin Polymers 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 239000012467 final product Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 125000000129 anionic group Chemical group 0.000 description 9
- 239000011230 binding agent Substances 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- ZBJVLWIYKOAYQH-UHFFFAOYSA-N naphthalen-2-yl 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=C(C=CC=C2)C2=C1 ZBJVLWIYKOAYQH-UHFFFAOYSA-N 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 238000010586 diagram Methods 0.000 description 7
- 239000004816 latex Substances 0.000 description 7
- 229920000126 latex Polymers 0.000 description 7
- 150000004760 silicates Chemical class 0.000 description 7
- 238000005063 solubilization Methods 0.000 description 7
- 230000007928 solubilization Effects 0.000 description 7
- 238000010186 staining Methods 0.000 description 7
- 239000002023 wood Substances 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000000976 ink Substances 0.000 description 6
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical group [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 125000002091 cationic group Chemical group 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 5
- 239000012855 volatile organic compound Substances 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical compound [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000004070 electrodeposition Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- 229910052909 inorganic silicate Inorganic materials 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
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- 239000012860 organic pigment Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 description 1
- ZTFZSHLWORMEHO-UHFFFAOYSA-A pentaaluminum;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical class [Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O.[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O.[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O ZTFZSHLWORMEHO-UHFFFAOYSA-A 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- QYTADNXBXAIJFH-UHFFFAOYSA-N potassium;zinc;dioxido(dioxo)chromium Chemical class [K+].[Zn+2].[O-][Cr]([O-])(=O)=O QYTADNXBXAIJFH-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- ADUQGQSOYWRHCA-UHFFFAOYSA-J tetrasodium;hydroxide;phosphate Chemical compound [OH-].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])([O-])=O ADUQGQSOYWRHCA-UHFFFAOYSA-J 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- KYEXABOBIDNORD-UHFFFAOYSA-N triethoxysilane trimethoxysilane Chemical compound CO[SiH](OC)OC.CCO[SiH](OCC)OCC KYEXABOBIDNORD-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical compound CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical class [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical class [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/08—Metals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
- Silicon Polymers (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/100,840 US7893183B2 (en) | 2005-04-07 | 2005-04-07 | Epoxy silane oligomer and coating composition containing same |
| US11/100,840 | 2005-04-07 | ||
| PCT/US2006/011609 WO2006110331A1 (en) | 2005-04-07 | 2006-03-30 | Epoxy silane oligomer and coating composition containing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2603710A1 true CA2603710A1 (en) | 2006-10-19 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002603710A Abandoned CA2603710A1 (en) | 2005-04-07 | 2006-03-30 | Epoxy silane oligomer and coating composition containing same |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US7893183B2 (https=) |
| EP (2) | EP1896522B1 (https=) |
| JP (1) | JP5567266B2 (https=) |
| KR (1) | KR101361811B1 (https=) |
| CN (1) | CN101189281B (https=) |
| BR (1) | BRPI0610447B1 (https=) |
| CA (1) | CA2603710A1 (https=) |
| MX (1) | MX2007012264A (https=) |
| RU (1) | RU2007141168A (https=) |
| TW (1) | TW200704675A (https=) |
| WO (1) | WO2006110331A1 (https=) |
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| US7595372B2 (en) * | 2005-04-07 | 2009-09-29 | Momentive Performance Materials Inc. | Epoxy silane oligomer and coating composition containing same |
| US7732552B2 (en) | 2006-01-27 | 2010-06-08 | Momentive Performance Materials Inc. | Low VOC epoxy silane oligomer and compositions containing same |
| US20080206454A1 (en) * | 2007-02-27 | 2008-08-28 | Insight Equity A.P.X., L.P. (Dba Vision-Ease Lens) | Composition Of Primer Solution For Use With An Optical Article And Method Of Priming An Optical Article |
| DE102007036369A1 (de) | 2007-07-31 | 2009-02-05 | Eckart Gmbh | Metallic-Lack, Verfahren zu seiner Herstellung und Verwendungen desselben |
| DE102007038314A1 (de) * | 2007-08-14 | 2009-04-16 | Evonik Degussa Gmbh | Verfahren zur kontrollierten Hydrolyse und Kondensation von Epoxy-funktionellen Organosilanen sowie deren Condensation mit weiteren organofunktionellen Alkoxysilanen |
| DE102007038313A1 (de) * | 2007-08-14 | 2009-02-19 | Evonik Degussa Gmbh | Anorganisch-modifizierte Polyesterbindemittelzubereitung, Verfahren zur Herstellung und ihre Verwendung |
| MX2011001736A (es) † | 2008-08-15 | 2011-05-10 | Valspar Sourcing Inc | Composicion de recubrimiento de sustrato cementoso de auto-grabado. |
| CN101724341B (zh) * | 2008-10-31 | 2012-07-25 | 宝山钢铁股份有限公司 | 耐高温板坯标志喷印涂料 |
| JP5131647B2 (ja) * | 2009-06-17 | 2013-01-30 | 信越化学工業株式会社 | アミノ変性シリコーンマイクロエマルジョン調製用組成物、アミノ変性シリコーンマイクロエマルジョンの製造方法およびアミノ変性シリコーンマイクロエマルジョン |
| US20110293898A1 (en) * | 2010-05-28 | 2011-12-01 | Seiko Epson Corporation | Ink set, textile printing method and printed textile |
| DE102011111757A1 (de) * | 2011-08-24 | 2013-02-28 | Coventya Gmbh | Versiegelungsmittel sowie dessen Verwendung und versiegeltes metallisches Substrat |
| EP2599844A1 (en) | 2011-12-02 | 2013-06-05 | PPG Industries Ohio Inc. | Coating composition for a food or beverage can |
| US8728345B2 (en) | 2011-12-19 | 2014-05-20 | Momentive Performance Materials Inc. | Epoxy-containing polysiloxane oligomer compositions, process for making same and uses thereof |
| CN104203762B (zh) * | 2012-03-29 | 2017-10-17 | 陶氏环球技术有限责任公司 | 水性分散体 |
| CA2871737C (en) * | 2012-04-30 | 2020-08-25 | 3M Innovative Properties Company | High solar-reflectivity roofing granules utilizing low absorption components |
| EP2692778A1 (en) | 2012-07-31 | 2014-02-05 | Momentive Specialty Chemicals Research S.A. | Epoxy resins and silane aqueous co-dispersions and the uses thereof |
| EP3378905A1 (en) * | 2013-02-15 | 2018-09-26 | Momentive Performance Materials Inc. | Antifouling system comprising silicone hydrogel |
| FR3008102B1 (fr) * | 2013-07-03 | 2016-06-17 | A Et A Mader | Kit pour composition liante, procede de fabrication d'un revetement de protection sacrificielle contre la corrosion mettant en oeuvre ladite composition et support revetu d'un tel revetement |
| US20150068219A1 (en) | 2013-09-11 | 2015-03-12 | Astronautics Corporation Of America | High Porosity Particulate Beds Structurally Stabilized by Epoxy |
| WO2015041942A1 (en) * | 2013-09-18 | 2015-03-26 | Rohm And Haas Company | Aqueous coating composition |
| US10703927B2 (en) | 2014-04-10 | 2020-07-07 | 3M Innovative Properties Company | Adhesion promoting and/or dust suppression coating |
| FR3021324B1 (fr) * | 2014-05-23 | 2017-12-22 | A Et A Mader | Composition liante, procede de fabrication d'un revetement de protection sacrificielle contre la corrosion mettant en oeuvre ladite composition et support revetu d'un tel revetement |
| US9718983B2 (en) | 2014-05-30 | 2017-08-01 | Ppg Industries Ohio, Inc. | Coating composition for a food or beverage can |
| US10499451B2 (en) * | 2014-06-13 | 2019-12-03 | Apple Inc. | Adaptive C-DRX management |
| EP3208295B1 (en) * | 2014-09-30 | 2021-01-13 | Kaneka Corporation | Method for producing siloxane resin |
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| WO2019039881A1 (ko) * | 2017-08-24 | 2019-02-28 | 코오롱인더스트리 주식회사 | 코팅용 수지 조성물 및 이의 경화물을 코팅층으로 포함하는 코팅필름 |
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-
2005
- 2005-04-07 US US11/100,840 patent/US7893183B2/en active Active
-
2006
- 2006-03-30 KR KR1020077025772A patent/KR101361811B1/ko not_active Expired - Lifetime
- 2006-03-30 CN CN2006800198586A patent/CN101189281B/zh not_active Expired - Lifetime
- 2006-03-30 EP EP06748918A patent/EP1896522B1/en not_active Expired - Lifetime
- 2006-03-30 RU RU2007141168/04A patent/RU2007141168A/ru unknown
- 2006-03-30 WO PCT/US2006/011609 patent/WO2006110331A1/en not_active Ceased
- 2006-03-30 BR BRPI0610447-9A patent/BRPI0610447B1/pt active IP Right Grant
- 2006-03-30 CA CA002603710A patent/CA2603710A1/en not_active Abandoned
- 2006-03-30 MX MX2007012264A patent/MX2007012264A/es unknown
- 2006-03-30 JP JP2008505376A patent/JP5567266B2/ja not_active Expired - Fee Related
- 2006-03-30 EP EP11008435.7A patent/EP2428530B1/en not_active Expired - Lifetime
- 2006-04-07 TW TW095112575A patent/TW200704675A/zh unknown
-
2011
- 2011-01-14 US US13/006,917 patent/US8338531B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR20070119073A (ko) | 2007-12-18 |
| WO2006110331A1 (en) | 2006-10-19 |
| EP2428530A1 (en) | 2012-03-14 |
| EP1896522A1 (en) | 2008-03-12 |
| US8338531B2 (en) | 2012-12-25 |
| TW200704675A (en) | 2007-02-01 |
| MX2007012264A (es) | 2008-02-22 |
| EP1896522B1 (en) | 2012-05-30 |
| RU2007141168A (ru) | 2009-05-20 |
| KR101361811B1 (ko) | 2014-02-21 |
| US20110112221A1 (en) | 2011-05-12 |
| JP5567266B2 (ja) | 2014-08-06 |
| CN101189281A (zh) | 2008-05-28 |
| US7893183B2 (en) | 2011-02-22 |
| BRPI0610447A2 (pt) | 2010-06-22 |
| US20060225613A1 (en) | 2006-10-12 |
| CN101189281B (zh) | 2013-06-05 |
| JP2008537747A (ja) | 2008-09-25 |
| EP2428530B1 (en) | 2014-11-19 |
| BRPI0610447B1 (pt) | 2017-12-26 |
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