JP5567266B2 - エポキシシランオリゴマー及びそれを含有するコーティング組成物 - Google Patents
エポキシシランオリゴマー及びそれを含有するコーティング組成物 Download PDFInfo
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- JP5567266B2 JP5567266B2 JP2008505376A JP2008505376A JP5567266B2 JP 5567266 B2 JP5567266 B2 JP 5567266B2 JP 2008505376 A JP2008505376 A JP 2008505376A JP 2008505376 A JP2008505376 A JP 2008505376A JP 5567266 B2 JP5567266 B2 JP 5567266B2
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- silane
- coating
- water
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- 239000008199 coating composition Substances 0.000 title claims description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 122
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 118
- 229910000077 silane Inorganic materials 0.000 claims description 118
- 229910052751 metal Inorganic materials 0.000 claims description 102
- 239000002184 metal Substances 0.000 claims description 102
- 238000000034 method Methods 0.000 claims description 96
- 239000004593 Epoxy Substances 0.000 claims description 89
- 239000004094 surface-active agent Substances 0.000 claims description 81
- 239000004615 ingredient Substances 0.000 claims description 63
- 239000000178 monomer Substances 0.000 claims description 46
- 239000000463 material Substances 0.000 claims description 40
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 36
- 239000004327 boric acid Substances 0.000 claims description 34
- 230000008569 process Effects 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000003002 pH adjusting agent Substances 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 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
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 claims description 15
- 239000006184 cosolvent Substances 0.000 claims description 14
- -1 glycidoxy Chemical group 0.000 claims description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 12
- 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
- NWLSIXHRLQYIAE-UHFFFAOYSA-N oxiran-2-ylmethoxysilicon Chemical compound [Si]OCC1CO1 NWLSIXHRLQYIAE-UHFFFAOYSA-N 0.000 claims description 9
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 7
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 7
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-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
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 claims description 5
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 claims description 5
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- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 claims description 4
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000003456 ion exchange resin Substances 0.000 claims description 4
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-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 group COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 claims description 3
- DJCYDDALXPHSHR-UHFFFAOYSA-N 2-(2-propoxyethoxy)ethanol Chemical compound CCCOCCOCCO DJCYDDALXPHSHR-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
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 3
- 239000003945 anionic surfactant Substances 0.000 claims description 3
- 239000003093 cationic surfactant Substances 0.000 claims description 3
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 3
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 239000002736 nonionic surfactant Substances 0.000 claims description 3
- 229960005323 phenoxyethanol Drugs 0.000 claims description 3
- 235000011007 phosphoric acid Nutrition 0.000 claims description 3
- FECCQKBXUJUGSF-UHFFFAOYSA-N 5-methoxypentanoic acid Chemical compound COCCCCC(O)=O FECCQKBXUJUGSF-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- 229940028356 diethylene glycol monobutyl ether Drugs 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
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 claims description 2
- 229920001281 polyalkylene Polymers 0.000 claims 2
- 239000002841 Lewis acid Substances 0.000 claims 1
- RDURTRDFNKIFKC-UHFFFAOYSA-N acetic acid;1-butoxypropan-2-ol Chemical compound CC(O)=O.CCCCOCC(C)O RDURTRDFNKIFKC-UHFFFAOYSA-N 0.000 claims 1
- 230000003796 beauty Effects 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 1
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- 238000000576 coating method Methods 0.000 description 102
- 239000000203 mixture Substances 0.000 description 100
- 239000011248 coating agent Substances 0.000 description 84
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 82
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 65
- 230000032683 aging Effects 0.000 description 59
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 57
- 229910052725 zinc Inorganic materials 0.000 description 54
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
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- 235000010338 boric acid Nutrition 0.000 description 35
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 22
- 229910052739 hydrogen Inorganic materials 0.000 description 22
- 239000001257 hydrogen Substances 0.000 description 22
- 239000000945 filler Substances 0.000 description 18
- 239000000049 pigment Substances 0.000 description 16
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- 239000000443 aerosol Substances 0.000 description 15
- 239000003125 aqueous solvent Substances 0.000 description 15
- 239000002923 metal particle Substances 0.000 description 15
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000002723 alicyclic group Chemical group 0.000 description 12
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- 125000003545 alkoxy group Chemical group 0.000 description 6
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- 239000002023 wood Substances 0.000 description 6
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- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 4
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- 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 description 3
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- 229910002651 NO3 Inorganic materials 0.000 description 2
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- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
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- MSRJTTSHWYDFIU-UHFFFAOYSA-N octyltriethoxysilane Chemical compound CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 description 1
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- 238000010998 test method 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
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
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- 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)
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| 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 (3)
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| JP2008537747A JP2008537747A (ja) | 2008-09-25 |
| JP2008537747A5 JP2008537747A5 (https=) | 2012-07-26 |
| JP5567266B2 true JP5567266B2 (ja) | 2014-08-06 |
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| 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 |
| CN105504287A (zh) | 2014-10-09 | 2016-04-20 | 瓦克化学(中国)有限公司 | 硅烷低聚物组合物的制备方法及应用 |
| ES2785320T5 (es) * | 2014-12-04 | 2023-04-25 | Tokuyama Corp | Composición de revestimiento y producto óptico que tiene capa de revestimiento hecha a partir de dicha composición de revestimiento |
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| JP6557041B2 (ja) * | 2015-03-31 | 2019-08-07 | 株式会社カネカ | 光または熱硬化性樹脂組成物からなる積層体 |
| KR102803453B1 (ko) | 2016-01-27 | 2025-05-07 | 모멘티브 퍼포먼스 머티리얼즈 인크. | 오염물 부착 방지성 실리콘 코팅 조성물 |
| DE102017005280B4 (de) * | 2017-06-02 | 2021-02-11 | Metten Stein + Design Gmbh & Co. Kg | Verfahren zur Herstellung eines bedruckten Betonelements |
| WO2019039881A1 (ko) * | 2017-08-24 | 2019-02-28 | 코오롱인더스트리 주식회사 | 코팅용 수지 조성물 및 이의 경화물을 코팅층으로 포함하는 코팅필름 |
| KR102271026B1 (ko) * | 2017-09-04 | 2021-06-30 | 코오롱인더스트리 주식회사 | 다층구조를 가지는 하드코팅 필름 및 이를 포함하는 폴리이미드 필름 |
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| EP3873998A1 (en) * | 2018-11-02 | 2021-09-08 | Momentive Performance Materials Inc. | Coatings with early water resistance |
| CN109897182A (zh) * | 2019-03-02 | 2019-06-18 | 江西省龙海化工有限公司 | 一种水性大分子量硅烷偶联剂及其制备方法 |
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| EP3808788A1 (en) | 2019-10-17 | 2021-04-21 | Saint-Gobain Weber | Aqueous coating compositions based on self-crosslinking polyurethane dispersions |
| WO2021093941A1 (en) * | 2019-11-12 | 2021-05-20 | Archroma Ip Gmbh | Wood coating formulation |
| CN111218002B (zh) * | 2020-02-24 | 2021-06-08 | 华南理工大学 | 一种高折射率含硼和环氧基团的有机硅增粘剂及其制备方法与应用 |
| CN112029321A (zh) * | 2020-09-18 | 2020-12-04 | 科伦塑业集团股份有限公司 | 一种长效农膜防雾流滴剂及其制备方法 |
| KR102275810B1 (ko) * | 2020-12-10 | 2021-07-09 | 주식회사 해성특수지 | 웨트 온 웨트 인쇄 장치 |
| WO2022155081A1 (en) * | 2021-01-12 | 2022-07-21 | Glen Raven, Inc. | Polysiloxane compositions and coatings and methods for producing the same |
| EP4288497A1 (en) * | 2021-02-02 | 2023-12-13 | Momentive Performance Materials Inc. | Composition comprising organic functional alkoxysilanes and coating compositions comprising the same |
| CN113003574A (zh) * | 2021-04-07 | 2021-06-22 | 大连理工大学 | 一种高比表面积多孔材料的制备方法及其应用 |
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| CN113512196B (zh) * | 2021-07-19 | 2022-11-01 | 中交上海三航科学研究院有限公司 | 一种烃基硅醇的醇溶液及制备方法 |
| EP4265662A1 (en) | 2022-04-20 | 2023-10-25 | Saint-Gobain Weber France | Polyurethane-based coatings with high solar reflectance index |
| WO2024077328A1 (en) * | 2022-10-12 | 2024-04-18 | Duluxgroup (Australia) Pty Ltd | Aqueous coating composition |
| CN116179117A (zh) * | 2022-12-30 | 2023-05-30 | 浙江志强涂料有限公司 | 一种新型环保高粘建筑胶水及其制备方法 |
| CN115851023A (zh) * | 2022-12-30 | 2023-03-28 | 无锡华东锌盾科技有限公司 | 一种无溶剂重防腐底面合一涂料及其制备方法 |
| CN116987412A (zh) * | 2023-03-21 | 2023-11-03 | 江西宏柏新材料股份有限公司 | 一种用于提高水性涂料附着力的添加剂及其制备方法 |
| EP4480977A1 (en) | 2023-06-23 | 2024-12-25 | CertainTeed LLC | Polyurethane-based coatings and coated substrates |
| FR3151039A1 (fr) | 2023-07-12 | 2025-01-17 | Saint-Gobain Weber France | Composition d’étanchéification à base de polyuréthane et de poly(acétal de vinyle) |
| PL449450A1 (pl) * | 2024-08-02 | 2026-02-09 | Vent Trade Spółka Z Ograniczoną Odpowiedzialnością | Środek do nanopowłoki o właściwościach antykorozyjnych, hydrofobowych oraz oleofobowych do elementów stalowych ocynkowanych, zwłaszcza wentylacyjnych |
| CN118955817B (zh) * | 2024-10-16 | 2025-01-28 | 安徽博纳新材料科技有限公司 | 一种用于防腐涂料的耐酸碱型乳液增稠剂及其制备方法 |
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-
2005
- 2005-04-07 US US11/100,840 patent/US7893183B2/en active Active
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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
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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 |
| CN101189281A (zh) | 2008-05-28 |
| US7893183B2 (en) | 2011-02-22 |
| BRPI0610447A2 (pt) | 2010-06-22 |
| CA2603710A1 (en) | 2006-10-19 |
| 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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