JP5603007B2 - 有機ビスマス触媒を用いたアミノシラン末端含有ポリマーの調製方法、及びスズ触媒を用いずにそれにより得られる硬化ポリマー - Google Patents
有機ビスマス触媒を用いたアミノシラン末端含有ポリマーの調製方法、及びスズ触媒を用いずにそれにより得られる硬化ポリマー Download PDFInfo
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- JP5603007B2 JP5603007B2 JP2008531157A JP2008531157A JP5603007B2 JP 5603007 B2 JP5603007 B2 JP 5603007B2 JP 2008531157 A JP2008531157 A JP 2008531157A JP 2008531157 A JP2008531157 A JP 2008531157A JP 5603007 B2 JP5603007 B2 JP 5603007B2
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- Prior art keywords
- bismuth
- catalyst
- weight
- diisocyanate
- parts
- 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.)
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- 239000003054 catalyst Substances 0.000 title claims description 62
- 238000000034 method Methods 0.000 title claims description 45
- 229910052797 bismuth Inorganic materials 0.000 title claims description 25
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 title claims description 23
- 239000012974 tin catalyst Substances 0.000 title claims description 9
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 title claims description 8
- 229920000642 polymer Polymers 0.000 title description 17
- 229920005862 polyol Polymers 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 39
- 150000003077 polyols Chemical class 0.000 claims description 39
- 229920000570 polyether Polymers 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 30
- -1 aluminum compound Chemical class 0.000 claims description 29
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 28
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 28
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical group C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 17
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 16
- 150000002009 diols Chemical class 0.000 claims description 15
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- 239000012948 isocyanate Substances 0.000 claims description 13
- 150000002513 isocyanates Chemical class 0.000 claims description 12
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- 150000001622 bismuth compounds Chemical class 0.000 claims description 11
- 239000000945 filler Substances 0.000 claims description 10
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- 239000013522 chelant Substances 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
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- 150000001412 amines Chemical class 0.000 claims description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 6
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- NUMHJBONQMZPBW-UHFFFAOYSA-K bis(2-ethylhexanoyloxy)bismuthanyl 2-ethylhexanoate Chemical compound [Bi+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O NUMHJBONQMZPBW-UHFFFAOYSA-K 0.000 claims description 5
- NSPSPMKCKIPQBH-UHFFFAOYSA-K bismuth;7,7-dimethyloctanoate Chemical compound [Bi+3].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O NSPSPMKCKIPQBH-UHFFFAOYSA-K 0.000 claims description 5
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- 239000004014 plasticizer Substances 0.000 claims description 5
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 5
- 239000002318 adhesion promoter Substances 0.000 claims description 4
- 239000012963 UV stabilizer Substances 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 239000002274 desiccant Substances 0.000 claims description 3
- OJJSYTLVICNTMF-UHFFFAOYSA-H dibismuth 2,2,3,3-tetramethylheptanedioate Chemical compound [Bi+3].[Bi+3].CC(C)(CCCC([O-])=O)C(C)(C)C([O-])=O.CC(C)(CCCC([O-])=O)C(C)(C)C([O-])=O.CC(C)(CCCC([O-])=O)C(C)(C)C([O-])=O OJJSYTLVICNTMF-UHFFFAOYSA-H 0.000 claims description 3
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims description 3
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- FRDNYWXDODPUJV-UHFFFAOYSA-N n-ethyl-2-methyl-3-trimethoxysilylpropan-1-amine Chemical group CCNCC(C)C[Si](OC)(OC)OC FRDNYWXDODPUJV-UHFFFAOYSA-N 0.000 claims description 3
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- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 3
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- 125000005442 diisocyanate group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 2
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- 230000003078 antioxidant effect Effects 0.000 claims 1
- 230000003796 beauty Effects 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 claims 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229910052726 zirconium Inorganic materials 0.000 description 6
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 5
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- 239000000654 additive Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000012975 dibutyltin dilaurate Substances 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 3
- 125000005498 phthalate group Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 3
- 229940080818 propionamide Drugs 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003609 titanium compounds Chemical class 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- VNTDZUDTQCZFKN-UHFFFAOYSA-L zinc 2,2-dimethyloctanoate Chemical compound [Zn++].CCCCCCC(C)(C)C([O-])=O.CCCCCCC(C)(C)C([O-])=O VNTDZUDTQCZFKN-UHFFFAOYSA-L 0.000 description 3
- 150000003752 zinc compounds Chemical class 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 2
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
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- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- GAUBQPQDJSWNSN-CFYXSCKTSA-N dibutyl (Z)-but-2-enedioate 3-trimethoxysilylpropan-1-amine Chemical group CO[Si](OC)(OC)CCCN.CCCCOC(=O)\C=C/C(=O)OCCCC GAUBQPQDJSWNSN-CFYXSCKTSA-N 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical group CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 231100000584 environmental toxicity Toxicity 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- SMIDUPHNWFRONB-UHFFFAOYSA-N n,2-dimethyl-3-trimethoxysilylpropan-1-amine Chemical compound CNCC(C)C[Si](OC)(OC)OC SMIDUPHNWFRONB-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical group CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- KGNDVXPHQJMHLX-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)cyclohexanamine Chemical group CO[Si](OC)(OC)CCCNC1CCCCC1 KGNDVXPHQJMHLX-UHFFFAOYSA-N 0.000 description 1
- SWPRLROHVKTMPN-UHFFFAOYSA-N n-butyl-2-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CCCCNCC(C)C[Si](OC)(OC)OC SWPRLROHVKTMPN-UHFFFAOYSA-N 0.000 description 1
- YJOGKUUQSLYPQJ-UHFFFAOYSA-N n-ethyl-2,2-dimethyl-4-trimethoxysilylbutan-1-amine Chemical compound CCNCC(C)(C)CC[Si](OC)(OC)OC YJOGKUUQSLYPQJ-UHFFFAOYSA-N 0.000 description 1
- PNAUMDBGSPRGCS-UHFFFAOYSA-N n-ethyl-2-methyl-3-triethoxysilylpropan-1-amine Chemical compound CCNCC(C)C[Si](OCC)(OCC)OCC PNAUMDBGSPRGCS-UHFFFAOYSA-N 0.000 description 1
- 125000003110 organyloxy group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- DRNXZGJGRSUXHW-UHFFFAOYSA-N silyl carbamate Chemical compound NC(=O)O[SiH3] DRNXZGJGRSUXHW-UHFFFAOYSA-N 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
-
- 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
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/227—Catalysts containing metal compounds of antimony, bismuth or arsenic
-
- 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
- C08G18/48—Polyethers
-
- 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
- C08G2190/00—Compositions for sealing or packing joints
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/227,919 | 2005-09-15 | ||
| US11/227,919 US8232362B2 (en) | 2005-09-15 | 2005-09-15 | Preparation of amino-silane terminated polymer by using organic bismuth catalyst and cured polymer therefrom by using non-tin catalyst |
| PCT/US2006/034138 WO2007037915A2 (en) | 2005-09-15 | 2006-08-31 | Preparation of amino-silane terminated polymer by using organic bismuth catalyst and cured polymer therefrom by using non-tin catalyst |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009508985A JP2009508985A (ja) | 2009-03-05 |
| JP2009508985A5 JP2009508985A5 (cg-RX-API-DMAC10.html) | 2013-04-18 |
| JP5603007B2 true JP5603007B2 (ja) | 2014-10-08 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008531157A Expired - Fee Related JP5603007B2 (ja) | 2005-09-15 | 2006-08-31 | 有機ビスマス触媒を用いたアミノシラン末端含有ポリマーの調製方法、及びスズ触媒を用いずにそれにより得られる硬化ポリマー |
Country Status (12)
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2007231030A (ja) * | 2006-02-27 | 2007-09-13 | Shin Etsu Chem Co Ltd | 皮膜形成シリコーンエマルジョン組成物 |
| DE102006055739A1 (de) * | 2006-11-25 | 2008-05-29 | Bayer Materialscience Ag | Abformmassen |
| JP5154187B2 (ja) * | 2007-10-03 | 2013-02-27 | アイカ工業株式会社 | 上水道用表面ウレタン樹脂組成物 |
| DE102008021221A1 (de) * | 2008-04-28 | 2009-10-29 | Henkel Ag & Co. Kgaa | Härtbare Zusammensetzung auf Basis silylierter Polyurethane |
| DE102008047362A1 (de) | 2008-09-15 | 2010-04-15 | Henkel Ag & Co. Kgaa | Zusammensetzung zur Hautaufhellung |
| US8138297B2 (en) * | 2009-02-09 | 2012-03-20 | Momentive Performance Materials Inc. | Moisture-curable silylated polymer possessing improved storage stability |
| DE102009026679A1 (de) * | 2009-06-03 | 2010-12-16 | Henkel Ag & Co. Kgaa | Kleb- und Dichtstoffe auf Basis silanterminierter Bindemittel zum Verkleben und Abdichten von flexiblen Solarfolien / Photovoltaikmodulen |
| EP2477738B1 (en) * | 2009-09-15 | 2019-01-23 | Basf Se | Photo-latent titanium-chelate catalysts |
| DE102009046269A1 (de) | 2009-10-30 | 2011-05-05 | Henkel Ag & Co. Kgaa | Harnstoffgebundende Alkoxysilane zum Einsatz in Dicht- und Klebstoffen |
| DE102009057584A1 (de) * | 2009-12-09 | 2011-06-16 | Bayer Materialscience Ag | Polyurethane-Prepolymere |
| KR101130317B1 (ko) * | 2010-01-12 | 2012-03-26 | 도레이첨단소재 주식회사 | 연성회로기판 보강판용 접착제 조성물 및 이를 이용한 접착제 시트 |
| JP5769929B2 (ja) * | 2010-03-17 | 2015-08-26 | サンスター技研株式会社 | ポリウレタン樹脂 |
| KR20130108107A (ko) | 2010-06-01 | 2013-10-02 | 에디런)(세드라 비.브이. | 중합체 조성물, 그 조성물의 사용 방법 및 철도 트랙 구조체에서 그 조성물의 용도 |
| KR101123558B1 (ko) | 2011-03-14 | 2012-03-12 | 코오롱인더스트리 주식회사 | 친환경 소재를 적용한 폴리우레탄 조성물 및 이로부터 제조된 폴리우레탄 방수?바닥재 |
| JP5771048B2 (ja) * | 2011-04-05 | 2015-08-26 | コニシ株式会社 | 硬化性シリル化ウレタン系樹脂及びその製造方法 |
| US9394443B2 (en) * | 2011-11-10 | 2016-07-19 | Momentive Performance Materials, Inc. | Moisture curable organopolysiloxane composition |
| JP5679352B2 (ja) * | 2012-05-23 | 2015-03-04 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | 室温硬化性ケイ素基含有ポリマー組成物 |
| US20140058030A1 (en) * | 2012-08-23 | 2014-02-27 | Bayer Materialscience Llc | Silane-terminated polyurethane and rubber composite materials |
| DE102012223422A1 (de) | 2012-12-17 | 2014-06-18 | Henkel Ag & Co. Kgaa | Niedermodulige silanterminierte PU-Präpolymere |
| EP2774673A1 (de) | 2013-03-04 | 2014-09-10 | Nitrochemie Aschau GmbH | Katalysator für die Vernetzung von Siliconkautschukmassen |
| CN103146336B (zh) * | 2013-04-08 | 2014-08-06 | 株洲时代新材料科技股份有限公司 | 一种单组份硅烷改性聚氨酯密封胶及其制备方法 |
| EP2796493A1 (en) * | 2013-04-25 | 2014-10-29 | Huntsman International Llc | Composition comprising silylated polymers and polyhedral oligomeric metallo silsesquioxane |
| US9321878B2 (en) * | 2013-12-16 | 2016-04-26 | Momentive Performance Materials Inc. | Process for the preparation of silylated polyurethane polymers using titanium-containing and zirconium-containing catalysts |
| CA2939923C (en) | 2014-02-18 | 2022-07-05 | 3M Innovative Properties Company | Easy to apply air and water barrier articles |
| WO2015166745A1 (ja) * | 2014-04-28 | 2015-11-05 | 日東化成株式会社 | 電着塗料組成物、電着塗料組成物用触媒 |
| MX374370B (es) * | 2014-06-19 | 2025-03-06 | Huntsman Int Llc | Poliuretanos sililados. |
| EP3237699A1 (en) | 2014-12-22 | 2017-11-01 | 3M Innovative Properties Company | Air and water barrier articles |
| JP6536147B2 (ja) * | 2015-04-17 | 2019-07-03 | 東ソー株式会社 | ウレタンプレポリマー、及びそれを用いた２液型ウレタン粘着剤 |
| EP3337935A4 (en) | 2015-08-18 | 2019-06-05 | 3M Innovative Properties Company | SELF-SEALING ARTICLES WITH ELASTIC POROUS LAYER |
| KR102722165B1 (ko) | 2015-11-18 | 2024-10-28 | 다우 글로벌 테크놀로지스 엘엘씨 | 가수분해성 폴리에테르 모노실란으로 가소화된 단일-성분 수분 경화성 실란 밀봉제 |
| WO2017112756A1 (en) | 2015-12-22 | 2017-06-29 | 3M Innovative Properties Company | Roll including air and water barrier article and method of using the same |
| KR101790486B1 (ko) * | 2016-03-30 | 2017-10-25 | 주식회사 빅스 | 텍스타일 코팅용 친수성 수분산 폴리우레탄 수지 및 그 제조방법 |
| US11365328B2 (en) | 2017-02-23 | 2022-06-21 | 3M Innovative Properties Company | Air and water barrier article including inelastic porous layer |
| JP2020527640A (ja) * | 2017-07-21 | 2020-09-10 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェンＨｅｎｋｅｌ ＡＧ ＆ Ｃｏ． ＫＧａＡ | シリル化ポリウレタンおよびその製造方法 |
| EP3480234A1 (de) | 2017-11-03 | 2019-05-08 | Evonik Degussa GmbH | Block-copolymere, enthaltend polyester- und polyolefin-struktureinheiten, und deren verwendung |
| KR102669016B1 (ko) * | 2018-08-17 | 2024-05-23 | 와커 헤미 아게 | 실란-종결 중합체를 생성하는 방법 |
| EP4010184A1 (en) | 2019-08-07 | 2022-06-15 | 3M Innovative Properties Company | Tape, article including tape and composite layer, and related methods |
| CN110760264B (zh) * | 2019-09-29 | 2021-10-22 | 江苏凯伦建材股份有限公司 | 一种适用于水泥基层的沥青聚氨酯防水涂料及其制备方法和应用 |
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| JPWO2022064931A1 (cg-RX-API-DMAC10.html) * | 2020-09-25 | 2022-03-31 | ||
| CN113292958A (zh) * | 2021-05-20 | 2021-08-24 | 山东沃赛新材料科技有限公司 | 一种高透明度环保型硅烷改性聚醚密封胶及其制备方法 |
| CN116606415A (zh) * | 2023-05-31 | 2023-08-18 | 湖北回天新材料股份有限公司 | 梳型硅烷封端聚氨酯聚合物树脂及其制备方法和应用 |
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| JPS55164270A (en) * | 1979-06-07 | 1980-12-20 | Kuraray Co Ltd | Laminate |
| US4242490A (en) * | 1979-07-20 | 1980-12-30 | The General Tire & Rubber Company | Thermoset polyurethane prepared from a polypropylene ether triol obtained using a double metal cyanide complex catalyst, ethylene glycol and tolylene diisocyanate |
| US4345053A (en) * | 1981-07-17 | 1982-08-17 | Essex Chemical Corp. | Silicon-terminated polyurethane polymer |
| US4687851A (en) * | 1985-08-15 | 1987-08-18 | The Dow Chemical Company | Polyurethane elastomers prepared from high equivalent weight polyahls |
| US5106874A (en) * | 1989-06-16 | 1992-04-21 | The Dow Chemical Company | Process for preparing elastomeric polyurethane or polyurethane-urea polymers, and polyurethanes so prepared |
| DE3924308A1 (de) * | 1989-07-22 | 1991-01-31 | Bayer Ag | Mehrstufig haertende kunststoffe |
| US4985491A (en) * | 1989-10-05 | 1991-01-15 | Olin Corporation | Polyurethane sealants made using high molecular weight polyols prepared with double metal cyanide catalysts |
| US5100997A (en) * | 1990-05-29 | 1992-03-31 | Olin Corporation | Preparation of elastomers using high molecular weight polyols or polyamines, said polyols prepared using a double metal cyanide complex catalyst |
| US5136010A (en) * | 1990-09-28 | 1992-08-04 | Olin Corporation | Polyurethane elastomers and polyurea elastomers made using high functionality, low unsaturation level polyols prepared with double metal cyanide catalysts |
| US5116931A (en) * | 1990-09-28 | 1992-05-26 | Olin Corporation | Thermoset polyurethane elastomers and polyurea elastomers made using high functionality, low unsaturation level polyols prepared with double metal cyanide catalysts |
| US5096993A (en) * | 1990-11-02 | 1992-03-17 | Olin Corporation | Thermoplastic polyurethane elastomers and polyurea elastomers made using low unsaturation level polyols prepared with double metal cyanide catalysts |
| US5185420A (en) * | 1990-11-02 | 1993-02-09 | Olin Corporation | Thermoplastic polyurethane elastomers and polyurea elastomers made using low unsaturation level polyols prepared with double metal cyanide catalysts |
| US5266681A (en) * | 1992-08-03 | 1993-11-30 | Olin Corporation | Process and composition for providing double metal cyanide catalyzed polyols having enhanced reactivity |
| JP3296982B2 (ja) * | 1996-12-11 | 2002-07-02 | サンスター技研株式会社 | 一液型湿気硬化性組成物 |
| US5976669A (en) | 1996-12-20 | 1999-11-02 | 3M Innovative Properties Company | Retroreflective article having launderably durable bead-bond |
| US5852137A (en) * | 1997-01-29 | 1998-12-22 | Essex Specialty Products | Polyurethane sealant compositions |
| US5990257A (en) * | 1998-01-22 | 1999-11-23 | Witco Corporation | Process for producing prepolymers which cure to improved sealants, and products formed thereby |
| US6121354A (en) * | 1998-11-19 | 2000-09-19 | Bostik, Inc. | High performance single-component sealant |
| JP3477120B2 (ja) * | 1999-09-20 | 2003-12-10 | サンスター技研株式会社 | ２成分形硬化性組成物 |
| US20030225237A1 (en) * | 2002-05-31 | 2003-12-04 | Roesler Richard R. | Moisture-curable, polyether urethanes with reactive silane groups and their use as sealants, adhesives and coatings |
| US7115696B2 (en) * | 2002-05-31 | 2006-10-03 | Bayer Materialscience Llc | Moisture-curable, polyether urethanes with reactive silane groups and their use as sealants, adhesives and coatings |
| US6844413B2 (en) * | 2002-06-18 | 2005-01-18 | Bayer Materialscience Llc | Moisture-curable, polyether urethanes with reactive silane groups and their use as sealants, adhesives and coatings |
| US6749943B1 (en) * | 2002-07-02 | 2004-06-15 | 3M Innovative Properties Company | Silane based moisture curing hot-melt adhesives |
| DE10355318A1 (de) * | 2003-11-27 | 2005-06-23 | Wacker-Chemie Gmbh | Verfahren zur Herstellung von organyloxysilylterminierten Polymeren |
| US7009022B2 (en) * | 2003-12-15 | 2006-03-07 | Henkel Corporation | Moisture curable high strength, flexible RTV organic copolymer compositions and methods of preparation |
| JP4535764B2 (ja) * | 2004-04-09 | 2010-09-01 | サンスター技研株式会社 | ガラス面用プライマー組成物 |
| US7365145B2 (en) * | 2005-09-14 | 2008-04-29 | Momentive Performance Materials Inc. | Moisture curable silylated polymer containing free polyols for coating, adhesive and sealant application |
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2005
- 2005-09-15 US US11/227,919 patent/US8232362B2/en active Active
-
2006
- 2006-08-31 BR BRPI0616214-2A patent/BRPI0616214A2/pt active IP Right Grant
- 2006-08-31 WO PCT/US2006/034138 patent/WO2007037915A2/en not_active Ceased
- 2006-08-31 AU AU2006295277A patent/AU2006295277A1/en not_active Abandoned
- 2006-08-31 EP EP12002245.4A patent/EP2518094B1/en active Active
- 2006-08-31 CA CA002622156A patent/CA2622156A1/en not_active Abandoned
- 2006-08-31 EP EP06802760.6A patent/EP1943282B1/en active Active
- 2006-08-31 KR KR1020087006199A patent/KR101350769B1/ko not_active Expired - Fee Related
- 2006-08-31 JP JP2008531157A patent/JP5603007B2/ja not_active Expired - Fee Related
- 2006-08-31 RU RU2008114489/04A patent/RU2008114489A/ru not_active Application Discontinuation
- 2006-08-31 CN CN2006800342110A patent/CN101273074B/zh not_active Expired - Fee Related
- 2006-09-13 TW TW095133905A patent/TW200720308A/zh unknown
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2008
- 2008-03-14 NO NO20081347A patent/NO20081347L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007037915A3 (en) | 2007-06-14 |
| CA2622156A1 (en) | 2007-04-05 |
| RU2008114489A (ru) | 2009-10-20 |
| US20070060732A1 (en) | 2007-03-15 |
| JP2009508985A (ja) | 2009-03-05 |
| US8232362B2 (en) | 2012-07-31 |
| EP1943282A2 (en) | 2008-07-16 |
| EP2518094A1 (en) | 2012-10-31 |
| EP1943282B1 (en) | 2020-03-04 |
| WO2007037915A2 (en) | 2007-04-05 |
| CN101273074B (zh) | 2013-06-26 |
| TW200720308A (en) | 2007-06-01 |
| KR20080055831A (ko) | 2008-06-19 |
| EP2518094B1 (en) | 2017-12-27 |
| NO20081347L (no) | 2008-06-09 |
| CN101273074A (zh) | 2008-09-24 |
| KR101350769B1 (ko) | 2014-02-17 |
| BRPI0616214A2 (pt) | 2011-06-14 |
| AU2006295277A1 (en) | 2007-04-05 |
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