JP2004534895A - イソシアネート官能性非水性分散ポリマーを含有するコーティング組成物 - Google Patents
イソシアネート官能性非水性分散ポリマーを含有するコーティング組成物 Download PDFInfo
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- JP2004534895A JP2004534895A JP2003512287A JP2003512287A JP2004534895A JP 2004534895 A JP2004534895 A JP 2004534895A JP 2003512287 A JP2003512287 A JP 2003512287A JP 2003512287 A JP2003512287 A JP 2003512287A JP 2004534895 A JP2004534895 A JP 2004534895A
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- methacrylate
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- 239000008199 coating composition Substances 0.000 title claims description 46
- 239000004815 dispersion polymer Substances 0.000 title description 17
- 239000000203 mixture Substances 0.000 claims abstract description 92
- 239000000178 monomer Substances 0.000 claims abstract description 84
- 229920000642 polymer Polymers 0.000 claims abstract description 64
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 49
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000003381 stabilizer Substances 0.000 claims abstract description 37
- 239000011230 binding agent Substances 0.000 claims abstract description 23
- 238000005227 gel permeation chromatography Methods 0.000 claims abstract description 19
- 238000000576 coating method Methods 0.000 claims abstract description 16
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 16
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 16
- 239000011248 coating agent Substances 0.000 claims abstract description 15
- 239000007788 liquid Substances 0.000 claims abstract description 15
- 239000004793 Polystyrene Substances 0.000 claims abstract description 10
- 229920002223 polystyrene Polymers 0.000 claims abstract description 10
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 40
- 239000012948 isocyanate Substances 0.000 claims description 24
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 22
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 22
- 150000002513 isocyanates Chemical class 0.000 claims description 21
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 17
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 15
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 13
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 9
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 9
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 9
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims description 9
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 7
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 5
- 239000012986 chain transfer agent Substances 0.000 claims description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
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- BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
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- 125000000524 functional group Chemical group 0.000 abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
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- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 23
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- 238000001035 drying Methods 0.000 description 15
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- 239000008096 xylene Substances 0.000 description 15
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 12
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 11
- 239000000049 pigment Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 229910052500 inorganic mineral Inorganic materials 0.000 description 9
- 239000011707 mineral Substances 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 229920005862 polyol Polymers 0.000 description 8
- 239000013638 trimer Substances 0.000 description 8
- 125000005442 diisocyanate group Chemical group 0.000 description 7
- 238000002845 discoloration Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 150000003077 polyols Chemical class 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000012855 volatile organic compound Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
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- 238000010438 heat treatment Methods 0.000 description 5
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 5
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RQLGMECUXRQENU-UHFFFAOYSA-N 3,3-dimethylbutaneperoxoic acid Chemical compound CC(C)(C)CC(=O)OO RQLGMECUXRQENU-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
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- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
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- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
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- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
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- 125000003118 aryl group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
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- XDDLRVYDQACVBC-UHFFFAOYSA-N 10-oxo-10-(1,2,2,6,6-pentamethylpiperidin-4-yl)oxydecanoic acid Chemical compound CN1C(C)(C)CC(OC(=O)CCCCCCCCC(O)=O)CC1(C)C XDDLRVYDQACVBC-UHFFFAOYSA-N 0.000 description 1
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- ODKBBGGUUMCXFY-UHFFFAOYSA-N 2-(2-cyanopentan-2-yldiazenyl)-2-methylpentanenitrile Chemical compound CCCC(C)(C#N)N=NC(C)(C#N)CCC ODKBBGGUUMCXFY-UHFFFAOYSA-N 0.000 description 1
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- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
- C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
- C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
- C08G18/0871—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being organic
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/625—Polymers of alpha-beta ethylenically unsaturated carboxylic acids; hydrolyzed polymers of esters of these acids
- C08G18/6254—Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/63—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers
- C08G18/633—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers onto polymers of compounds having carbon-to-carbon double bonds
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/728—Polymerisation products of compounds having carbon-to-carbon unsaturated bonds and having isocyanate or isothiocyanate groups or groups forming isocyanate or isothiocyanate 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/901,394 US6632880B2 (en) | 2001-07-09 | 2001-07-09 | Coating compositions containing isocyanate-functional non-aqueous dispersed polymers |
| PCT/US2002/021528 WO2003006520A1 (en) | 2001-07-09 | 2002-07-09 | Coating compositions containing isocyanate-functional non-aqueous dispersed polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004534895A true JP2004534895A (ja) | 2004-11-18 |
| JP2004534895A5 JP2004534895A5 (OSRAM) | 2006-01-05 |
Family
ID=25414082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003512287A Pending JP2004534895A (ja) | 2001-07-09 | 2002-07-09 | イソシアネート官能性非水性分散ポリマーを含有するコーティング組成物 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US6632880B2 (OSRAM) |
| EP (1) | EP1425324B1 (OSRAM) |
| JP (1) | JP2004534895A (OSRAM) |
| KR (1) | KR20040018433A (OSRAM) |
| CN (1) | CN1529724A (OSRAM) |
| AT (1) | ATE412677T1 (OSRAM) |
| BR (1) | BR0211230A (OSRAM) |
| CA (1) | CA2449461A1 (OSRAM) |
| DE (1) | DE60229652D1 (OSRAM) |
| ES (1) | ES2316578T3 (OSRAM) |
| MX (1) | MXPA04000202A (OSRAM) |
| TW (1) | TWI250195B (OSRAM) |
| WO (1) | WO2003006520A1 (OSRAM) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010001773A1 (ja) * | 2008-07-01 | 2010-01-07 | 昭和電工株式会社 | 塗料組成物及びこれを用いた塗膜形成方法 |
| JP2013540177A (ja) * | 2010-09-29 | 2013-10-31 | ジーカ テクノロジー アクチェンゲゼルシャフト | 超分岐ポリマーを基剤とする二成分形ポリウレタン |
| JP5386366B2 (ja) * | 2007-11-28 | 2014-01-15 | 三井化学株式会社 | 反応射出成形用ポリウレタン樹脂組成物および成形品 |
| WO2023210448A1 (ja) * | 2022-04-25 | 2023-11-02 | 株式会社トクヤマ | 硬化性組成物、硬化体、積層体、光学物品、レンズ、及び眼鏡 |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4673962B2 (ja) * | 2000-08-25 | 2011-04-20 | 楠本化成株式会社 | クリアー型塗料塗膜の耐水白化性を有する消泡剤或いは平滑剤 |
| CA2449369C (en) * | 2001-06-15 | 2011-08-23 | Huntsman Petrochemical Corporation | Synergistic amine chain-extenders in polyurea spray elastomers |
| DE10357712A1 (de) * | 2003-12-09 | 2005-07-14 | Bayer Materialscience Ag | Härter |
| US20080102119A1 (en) * | 2006-11-01 | 2008-05-01 | Medtronic, Inc. | Osmotic pump apparatus and associated methods |
| EP1574533B1 (en) * | 2004-03-09 | 2007-11-14 | Rohm And Haas Company | Aqueous dispersion of polymeric particles |
| EP1574555B1 (en) * | 2004-03-11 | 2007-04-11 | Rohm And Haas Company | Aqueous polymer dispersion and method of use |
| US8090082B2 (en) * | 2006-01-23 | 2012-01-03 | Icall, Inc. | System, method and computer program product for extracting user profiles and habits based on speech recognition and calling history for telephone system advertising |
| US8206827B2 (en) | 2007-03-15 | 2012-06-26 | Nanovere Technologies, Llc | Dendritic polyurethane coating |
| US8568888B2 (en) | 2007-03-15 | 2013-10-29 | Nanovere Technologies, Inc. | Dendritic polyurethane coating |
| US9309433B2 (en) * | 2007-12-28 | 2016-04-12 | Axalta Coating Systems Ip Co., Llc | Radiation and chemical curable coating composition |
| US8198370B2 (en) * | 2007-12-28 | 2012-06-12 | E I Du Pont De Nemours And Company | Coated substrate |
| US8030408B2 (en) * | 2008-08-29 | 2011-10-04 | E. I. Du Pont De Nemours And Company | Tricure acrylic resins |
| US20100055480A1 (en) * | 2008-08-29 | 2010-03-04 | Patricia Mary Ellen Sormani | Process for preparing tricure resins |
| JP4701293B2 (ja) * | 2009-01-23 | 2011-06-15 | 関西ペイント株式会社 | 複層塗膜形成方法 |
| US9469797B2 (en) | 2010-08-11 | 2016-10-18 | Regents Of The University Of Minnesota | Pressure-sensitive adhesives having high bio-based content and macromonomers for preparing same |
| JP5948164B2 (ja) * | 2012-06-28 | 2016-07-06 | Ｂａｓｆジャパン株式会社 | 複層塗膜形成方法 |
| US11407905B2 (en) * | 2017-03-01 | 2022-08-09 | Ppg Industries Ohio, Inc. | Electrodepositable coating compositions |
| CN107860833A (zh) * | 2017-10-20 | 2018-03-30 | 广东生益科技股份有限公司 | 氰酸酯单体含量的测定方法 |
| EP3489268A1 (en) * | 2017-11-23 | 2019-05-29 | Allnex Belgium, S.A. | Radiation curable composition |
| KR20210142618A (ko) * | 2019-03-18 | 2021-11-25 | 알넥스 네덜란드 비. 브이. | 비수성 가교성 조성물 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4134935A (en) * | 1971-08-12 | 1979-01-16 | Bayer Aktiengesellschaft | Dental varnishes |
| US4528317A (en) | 1983-01-05 | 1985-07-09 | Ford Motor Company | Non-aqueous dispersions based on capped stabilizers and reactants comprising polyfunctional monomers II |
| US5010140A (en) | 1989-05-31 | 1991-04-23 | E. I. Du Pont De Nemours And Company | Process for preparing stabilized polymer dispersion |
| US5021177A (en) * | 1990-04-23 | 1991-06-04 | Texaco Inc. | Dispersant-antioxidant multifunctional viscosity index improver |
| US5231137A (en) * | 1990-08-23 | 1993-07-27 | American Cyanamid Company | Isopropenyl-alpha,alpha-dimethylbenzyl isocyanate - grafted polymers |
| US5286782A (en) | 1992-08-31 | 1994-02-15 | E. I. Du Pont De Nemours And Company | Coating composition of an acrylic polymer, polyol and polyisocyanate crosslinking agent |
| US5310807A (en) * | 1992-12-30 | 1994-05-10 | E. I. Du Pont De Nemours And Company | Star polymers made from macromonomers made by cobalt chain transfer process |
| GB9525914D0 (en) | 1995-12-19 | 1996-02-21 | Ici Plc | Aqueous dispersion |
| US5763528A (en) | 1996-12-17 | 1998-06-09 | E. I. Du Pont De Nemours And Company | Coating compositions containing non-aqueous dispersed polymers having a high glass transition temperature |
| US6221494B1 (en) | 1998-11-03 | 2001-04-24 | E.I. Du Pont De Nemours And Company | Reactive oligomers for isocyanate coatings |
| US7071264B2 (en) * | 2003-09-09 | 2006-07-04 | E.I. Du Pont De Nemours And Company | Branched polymers and coating compositions made therefrom |
-
2001
- 2001-07-09 US US09/901,394 patent/US6632880B2/en not_active Expired - Fee Related
-
2002
- 2002-07-02 TW TW091114627A patent/TWI250195B/zh not_active IP Right Cessation
- 2002-07-09 AT AT02746920T patent/ATE412677T1/de not_active IP Right Cessation
- 2002-07-09 EP EP02746920A patent/EP1425324B1/en not_active Expired - Lifetime
- 2002-07-09 DE DE60229652T patent/DE60229652D1/de not_active Expired - Fee Related
- 2002-07-09 ES ES02746920T patent/ES2316578T3/es not_active Expired - Lifetime
- 2002-07-09 WO PCT/US2002/021528 patent/WO2003006520A1/en not_active Ceased
- 2002-07-09 CN CNA028138600A patent/CN1529724A/zh active Pending
- 2002-07-09 MX MXPA04000202A patent/MXPA04000202A/es unknown
- 2002-07-09 CA CA002449461A patent/CA2449461A1/en not_active Abandoned
- 2002-07-09 JP JP2003512287A patent/JP2004534895A/ja active Pending
- 2002-07-09 BR BR0211230-2A patent/BR0211230A/pt not_active IP Right Cessation
- 2002-07-09 KR KR10-2004-7000238A patent/KR20040018433A/ko not_active Withdrawn
-
2003
- 2003-09-29 US US10/673,831 patent/US7479525B2/en not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5386366B2 (ja) * | 2007-11-28 | 2014-01-15 | 三井化学株式会社 | 反応射出成形用ポリウレタン樹脂組成物および成形品 |
| WO2010001773A1 (ja) * | 2008-07-01 | 2010-01-07 | 昭和電工株式会社 | 塗料組成物及びこれを用いた塗膜形成方法 |
| JP5615704B2 (ja) * | 2008-07-01 | 2014-10-29 | 昭和電工株式会社 | 塗料組成物及びこれを用いた塗膜形成方法 |
| JP2013540177A (ja) * | 2010-09-29 | 2013-10-31 | ジーカ テクノロジー アクチェンゲゼルシャフト | 超分岐ポリマーを基剤とする二成分形ポリウレタン |
| WO2023210448A1 (ja) * | 2022-04-25 | 2023-11-02 | 株式会社トクヤマ | 硬化性組成物、硬化体、積層体、光学物品、レンズ、及び眼鏡 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20040072955A1 (en) | 2004-04-15 |
| EP1425324B1 (en) | 2008-10-29 |
| US7479525B2 (en) | 2009-01-20 |
| DE60229652D1 (de) | 2008-12-11 |
| US6632880B2 (en) | 2003-10-14 |
| CN1529724A (zh) | 2004-09-15 |
| US20030018124A1 (en) | 2003-01-23 |
| EP1425324A1 (en) | 2004-06-09 |
| BR0211230A (pt) | 2004-08-10 |
| MXPA04000202A (es) | 2004-03-18 |
| ATE412677T1 (de) | 2008-11-15 |
| KR20040018433A (ko) | 2004-03-03 |
| ES2316578T3 (es) | 2009-04-16 |
| WO2003006520A1 (en) | 2003-01-23 |
| TWI250195B (en) | 2006-03-01 |
| CA2449461A1 (en) | 2003-01-23 |
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