JP2009507985A - コーティング、接着材及びシーラント用途に用いられる、フリーのポリオールを含有する水分硬化性シリル化ポリマー - Google Patents
コーティング、接着材及びシーラント用途に用いられる、フリーのポリオールを含有する水分硬化性シリル化ポリマー Download PDFInfo
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- JP2009507985A JP2009507985A JP2008531121A JP2008531121A JP2009507985A JP 2009507985 A JP2009507985 A JP 2009507985A JP 2008531121 A JP2008531121 A JP 2008531121A JP 2008531121 A JP2008531121 A JP 2008531121A JP 2009507985 A JP2009507985 A JP 2009507985A
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- Prior art keywords
- polyol
- moisture curable
- curable composition
- silylated polymer
- catalyst
- 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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- 229920005862 polyol Polymers 0.000 title claims abstract description 101
- 150000003077 polyols Chemical class 0.000 title claims abstract description 98
- 229920000642 polymer Polymers 0.000 title claims abstract description 60
- 238000000576 coating method Methods 0.000 title claims description 8
- 239000011248 coating agent Substances 0.000 title claims description 3
- 239000013466 adhesive and sealant Substances 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 63
- 239000003054 catalyst Substances 0.000 claims abstract description 44
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 25
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 21
- -1 mannide Chemical compound 0.000 claims description 21
- 229920000570 polyether Polymers 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 14
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 13
- 150000001412 amines Chemical group 0.000 claims description 12
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 9
- 229920005906 polyester polyol Polymers 0.000 claims description 9
- 239000000565 sealant Substances 0.000 claims description 9
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 8
- 229910000077 silane Inorganic materials 0.000 claims description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 claims description 6
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 6
- 239000000853 adhesive Substances 0.000 claims description 6
- 230000001070 adhesive effect Effects 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 6
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical compound [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 claims description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 5
- 229920000058 polyacrylate Polymers 0.000 claims description 5
- 229920000098 polyolefin Polymers 0.000 claims description 5
- 229920006324 polyoxymethylene Polymers 0.000 claims description 5
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229930195725 Mannitol Natural products 0.000 claims description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 4
- 229930006000 Sucrose Natural products 0.000 claims description 4
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000000594 mannitol Substances 0.000 claims description 4
- 235000010355 mannitol Nutrition 0.000 claims description 4
- 150000002902 organometallic compounds Chemical group 0.000 claims description 4
- 239000004014 plasticizer Substances 0.000 claims description 4
- 229920000515 polycarbonate Polymers 0.000 claims description 4
- 239000004417 polycarbonate Substances 0.000 claims description 4
- 229920006149 polyester-amide block copolymer Polymers 0.000 claims description 4
- 229920006295 polythiol Polymers 0.000 claims description 4
- 239000000600 sorbitol Substances 0.000 claims description 4
- 239000005720 sucrose Substances 0.000 claims description 4
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 239000012963 UV stabilizer Substances 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 3
- 229940051250 hexylene glycol Drugs 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 235000000346 sugar Nutrition 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 239000004606 Fillers/Extenders Substances 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 229910052797 bismuth Inorganic materials 0.000 claims description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 claims description 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 229930182470 glycoside Natural products 0.000 claims description 2
- 150000002338 glycosides Chemical class 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- 150000003754 zirconium Chemical class 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 238000013008 moisture curing Methods 0.000 claims 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims 1
- 230000000704 physical effect Effects 0.000 abstract description 12
- 239000004432 silane-modified polyurethane Substances 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 13
- 150000002009 diols Chemical class 0.000 description 10
- 229920002635 polyurethane Polymers 0.000 description 10
- 239000004814 polyurethane Substances 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 229920005903 polyol mixture Polymers 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 5
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000012975 dibutyltin dilaurate Substances 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical class OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000005056 polyisocyanate Substances 0.000 description 5
- 229920001228 polyisocyanate Polymers 0.000 description 5
- 150000004756 silanes Chemical class 0.000 description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 235000019256 formaldehyde Nutrition 0.000 description 3
- 238000006459 hydrosilylation reaction Methods 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- FRDNYWXDODPUJV-UHFFFAOYSA-N n-ethyl-2-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CCNCC(C)C[Si](OC)(OC)OC FRDNYWXDODPUJV-UHFFFAOYSA-N 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
- 150000004072 triols Chemical class 0.000 description 3
- XDFJBMAPHNLKKR-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]-n-ethyl-2-methylpropan-1-amine Chemical compound CCNCC(C)C[Si](C)(OC)OC XDFJBMAPHNLKKR-UHFFFAOYSA-N 0.000 description 2
- KNYSNQHOKNRINQ-UHFFFAOYSA-N 4-(dimethoxymethylsilyl)-N-ethyl-2,2-dimethylbutan-1-amine Chemical compound CCNCC(C)(C)CC[SiH2]C(OC)OC KNYSNQHOKNRINQ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 2
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- XCOASYLMDUQBHW-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)butan-1-amine Chemical group CCCCNCCC[Si](OC)(OC)OC XCOASYLMDUQBHW-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- PABWYMSXHPGZFP-UHFFFAOYSA-N 2-methyl-3-trimethoxysilyl-n-(3-trimethoxysilylpropyl)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCC(C)C[Si](OC)(OC)OC PABWYMSXHPGZFP-UHFFFAOYSA-N 0.000 description 1
- QXULZQKARBZMBR-UHFFFAOYSA-N 2-methyl-n-(3-trimethoxysilylpropyl)propan-2-amine Chemical group CO[Si](OC)(OC)CCCNC(C)(C)C QXULZQKARBZMBR-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- TZZGHGKTHXIOMN-UHFFFAOYSA-N 3-trimethoxysilyl-n-(3-trimethoxysilylpropyl)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCCC[Si](OC)(OC)OC TZZGHGKTHXIOMN-UHFFFAOYSA-N 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical group CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 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 1
- 239000004571 lime Substances 0.000 description 1
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- 125000005394 methallyl group Chemical group 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000178 monomer Substances 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
- 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
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-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
- OKIKLSJWTXOVSF-UHFFFAOYSA-N n-methyl-2-(3-trimethoxysilylpropoxy)propan-1-amine Chemical compound CNCC(C)OCCC[Si](OC)(OC)OC OKIKLSJWTXOVSF-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
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- 239000011368 organic material Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
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- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 238000004448 titration Methods 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
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
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- 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
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- 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
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- C08G18/4825—Polyethers containing two hydroxy groups
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- 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
- C08G18/71—Monoisocyanates or monoisothiocyanates
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/83—Chemically modified polymers
- C08G18/831—Chemically modified polymers by oxygen-containing compounds inclusive of carbonic acid halogenides, carboxylic acid halogenides and epoxy halides
- C08G18/832—Chemically modified polymers by oxygen-containing compounds inclusive of carbonic acid halogenides, carboxylic acid halogenides and epoxy halides by water acting as hydrolizing agent
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C08L101/10—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing hydrolysable silane groups
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- C—CHEMISTRY; METALLURGY
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Abstract
【解決手段】水分硬化性組成物であって、a)シリル化ポリマーと、b)少なくとも1つのポリオールと、c)前記シリル化ポリマーと前記ポリオールとの反応に用いられる触媒を含む、実質的に水分を含まない混合物を含んでなる組成物。
【選択図】なし
Description
a)シリル化ポリマーと、
b)少なくとも1つのポリオールと、
c)前記シリル化ポリマーと前記ポリオールとの反応に用いられる触媒を含む、実質的に水分を含まない混合物を含んでなる組成物の提供に関する。当該水分硬化性組成物中の当該シリル化ポリマーは、
(i)イソシアナトシランとポリオールとの反応から得られるシリル化ポリマー、
(ii)イソシアナトシランと水酸基末端を有するポリウレタンプレポリマーとの反応から得られるシリル化ポリマー、
(iii)イソシアナト末端ポリウレタンプレポリマーと水素活性有機官能性シランとの反応から得られるシリル化ポリマー、及び
(iv)シラン末端を有するポリエーテルから得られるシリル化ポリマー、からなる群から選択される少なくとも1つのメンバーである。
(a)上記したシリル化ポリマーと、
(b)少なくとも1つのポリオールと、
(c)触媒を混合することを含んでなる方法の提供に関する。
Acclaim(登録商標)4200(ポリオキシプロピレンジオール、Mn=4,000、官能基=2、Bayer社製)、
MDI Desmodur(登録商標)M−0129(Bayer社製、約55%の2,4−MDI及び45%の4,4−MDIを含有するMDI)、
A−Link(登録商標)15(N−エチル−3−トリメトキシシリル−2−メチル−プロパンアミン、ゼネラルエレクトリック(GE)社製)、
SUL−4(Formerz、ゼネラルエレクトリック社製のジブチルスズジラウレート)。
ケトルにジオールを添加した。ケトルを撹拌しながら、及び適度なフロー速度で窒素ガスを分散させながら、600℃に加熱した。一晩、あるいは水分濃度がカール・フィッシャー滴定で200ppm未満となるまでこの乾燥工程を継続させた。ケトルを30℃に冷却し、GCシリンジ又は自動ピペットを使用してリアクターに触媒を添加した。触媒をよく混合した後、イソシアネートを添加し、加熱を開始した。温度を65℃に維持し、滴定によってイソシアネートの含有をモニターした。イソシアネート(NCO)含有がキャッピングポイント(例えば0.67%)に達したとき、シランカップリング剤(A−Link 15)を添加し、フリーのNCOが検出されなくなるまで65℃で反応を継続させた。
* Accalaim 8200:低不飽和ポリエーテルポリオール、Mn=8000、fn−2、Bayer社製。
** GEP 330N:EOでキャッピングされたポリエーテルポリオール、Mn=5000、fn=3、Shanghai Gaoqiao Petrochem(SGP)社製。
*** GR−835G:スクロースから開始するポリエーテルポリオール、OH=410mg KOH/g、SGP社製。
**** 5120:AA/DEG/EGベースのポリエステルポリオール、OH=53−59mg KOH/g、fn=2、Eternal Chem社製。
***** Stepanpol PD−110LV:芳香族ポリエステル、OH=110mg KOH/g、fn=2、Stepan社製。
* Acclaim(登録商標)4200:低不飽和ポリオキシプロピレンジオール、Mn=4,000、官能性:2、Bayer社製。
** GE−220:ポリエーテルポリオール、Mn=2000、fn=2、Shanghai Gaoqiao Petrochem(SGP)社製。
*** BDO:1,4−ブタンジオール。
**** TTA:トリエタノールアミン。
***** DEG:ジグリコール。
Claims (20)
- シリル化ポリマーと、
少なくとも1つのポリオールと、
前記シリル化ポリマーと前記ポリオールとの反応のための触媒を含んでなり、水分を実質的に含有しない、水分硬化性組成物。 - 前記水分硬化性組成物中の前記シリル化ポリマーが、
(i)イソシアナトシランとポリオールとの反応から得られるシリル化ポリマー、
(ii)イソシアナトシランと水酸基末端を有するポリウレタンプレポリマーとの反応から得られるシリル化ポリマー、
(iii)イソシアナト末端ポリウレタンプレポリマーと水素活性有機官能性シランとの反応から得られるシリル化ポリマー、及び
(iv)シラン末端を有するポリエーテルから得られるシリル化ポリマー、からなる群から選択される少なくとも1つのメンバーである、請求項1記載の水分硬化性組成物。 - 前記ポリオールが少なくとも2つの水酸基を有する、請求項1記載の水分硬化性組成物。
- 前記ポリオールが、脂肪族及び芳香族ポリエステルポリオール、ポリエーテルポリオール、ポリヒドロキシポリカーボネート、ポリヒドロキシポリアセタール、ポリヒドロキシポリアクリレート、ポリヒドロキシポリエステルアミド及びポリヒドロキシポリチオエーテル、ポリオレフィンポリオール、並びにそれらの混合物からなる群から選択される高分子量ポリオールである、請求項1記載の水分硬化性組成物。
- 前記ポリオールがアルコール、グリコール、グリセリン、トリメチロールプロパン、ペンタエリトリトール、グリコシド、糖、アルキルオールアミン及びそれらの混合物からなる群から選択される低分子量ポリオールである、請求項1記載の水分硬化性組成物。
- 前記ポリオールが、グリコール、トリエチレングリコール、プロピレングリコール、ブタンジオール、ヘキシレングリコール、トリメチロールプロパン、ジエチレングリコール、ジプロピレングリコール、マンナイド、1,2,6−ヘキサントリオール、1,2,4−ブタントリオール、トリメチロールエタン、ペンタエリトリトール、マンニトール、ソルビトール、蔗糖、ジエタノールアミン、トリエタノールアミン及びそれらの混合物からなる群から選択される、請求項5記載の水分硬化性組成物。
- 前記シリル化ポリマーが、少なくとも200当量を有する高分子量ポリオールと混合されている、請求項4記載の水分硬化性組成物。
- 前記シリル化ポリマーが、約400〜約20,000当量を有する高分子量ポリオールと混合されている、請求項4記載の水分硬化性組成物。
- 前記シリル化ポリマーが、約500〜約18,000当量を有する高分子量ポリオールと混合されている、請求項4記載の水分硬化性組成物。
- 前記ポリオールが、高分子量ポリオールと低分子量ポリオールとの混合物である、請求項1記載の水分硬化性組成物。
- 前記ポリオールが、前記シリル化ポリマー中のアルコキシル基1モル当たり、1〜100モル%のヒドロキシル基を有するレベルで存在する、請求項1記載の水分硬化性組成物。
- 前記ポリオールが、前記シリル化ポリマー中のアルコキシル基1モル当たり、5〜80モル%のヒドロキシル基を有するレベルで存在する、請求項1記載の水分硬化性組成物。
- 前記ポリオールが、前記シリル化ポリマー中のアルコキシル基1モル当たり、5〜50モル%のヒドロキシル基を有するレベルで存在する、請求項1記載の水分硬化性組成物。
- 前記触媒が有機金属化合物触媒である、請求項1記載の水分硬化性組成物。
- 前記触媒がアミン触媒である、請求項1記載の水分硬化性組成物。
- 前記触媒が、第1級アミン、第2級アミン、第3級アミン、アミノシラン及びそれらの混合物からなる郡から選択されるアミン触媒である、請求項1記載の水分硬化性組成物。
- 前記触媒が、有機ジブチルスズ、ジルコニウム錯体、アルミニウムキレート、チタンキレート、有機亜鉛、有機コバルト、有機鉄、有機ニッケル及び有機ビスマス及びそれらの混合物からなる群から選択される、請求項14記載の水分硬化性組成物。
- 前記触媒が有機金属化合物触媒及びアミン触媒の混合物である、請求項1記載の水分硬化性組成物。
- 請求項1記載の水分硬化性組成物を用いて調製される、水分硬化性のシーラント、コーティング又は接着剤。
- 任意に添加剤、充填剤、染料、可塑剤、増粘剤、カップリング剤、増量剤及びUV安定化剤及び/又はその混合物のうちの少なくとも1つを含有する、請求項1記載の水分硬化性組成物。
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US11/226,760 US7365145B2 (en) | 2005-09-14 | 2005-09-14 | Moisture curable silylated polymer containing free polyols for coating, adhesive and sealant application |
PCT/US2006/032434 WO2007037833A2 (en) | 2005-09-14 | 2006-08-21 | Moisture curable silylated polymer containing free polyols for coating, adhesive and sealant application |
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FR2863624B1 (fr) * | 2003-12-11 | 2007-02-09 | Bostik Findley | Compositions adhesives recticulables a l'humidite |
US8232362B2 (en) * | 2005-09-15 | 2012-07-31 | Momentive Performance Materials Inc. | Preparation of amino-silane terminated polymer by using organic bismuth catalyst and cured polymer therefrom by using non-tin catalyst |
US20090030145A1 (en) * | 2007-07-26 | 2009-01-29 | Bayer Materialscience Llc | Hydrophilic sealants |
WO2010096110A1 (en) * | 2008-10-29 | 2010-08-26 | Dow Global Technologies, Inc. | Low energy surface bonding system containing a primer with long open time |
DE102009022631A1 (de) | 2009-05-25 | 2010-12-16 | Evonik Goldschmidt Gmbh | Härtbare Silylgruppen enthaltende Zusammensetzungen und deren Verwendung |
DE102009034607A1 (de) | 2009-07-24 | 2011-01-27 | Evonik Goldschmidt Gmbh | Neuartige Siliconpolyethercopolymere und Verfahren zu deren Herstellung |
DE102009028636A1 (de) | 2009-08-19 | 2011-02-24 | Evonik Goldschmidt Gmbh | Neuartige Urethangruppen enthaltende silylierte Präpolymere und Verfahren zu deren Herstellung |
DE102009028640A1 (de) | 2009-08-19 | 2011-02-24 | Evonik Goldschmidt Gmbh | Härtbare Masse enthaltend Urethangruppen aufweisende silylierte Polymere und deren Verwendung in Dicht- und Klebstoffen, Binde- und/oder Oberflächenmodifizierungsmitteln |
DE102010001528A1 (de) | 2010-02-03 | 2011-08-04 | Evonik Goldschmidt GmbH, 45127 | Neue Partikel und Kompositpartikel, deren Verwendungen und ein neues Verfahren zu deren Herstellung aus Alkoxysilylgruppen tragenden Alkoxylierungsprodukten |
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 |
US8822606B2 (en) | 2010-06-30 | 2014-09-02 | Dow Global Technologies Llc | Low viscosity silyl-terminated polymers |
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CA2622147A1 (en) | 2007-04-05 |
CN101263202A (zh) | 2008-09-10 |
US20070060714A1 (en) | 2007-03-15 |
RU2008114381A (ru) | 2009-10-20 |
KR20080050415A (ko) | 2008-06-05 |
US7365145B2 (en) | 2008-04-29 |
CN101263202B (zh) | 2012-02-29 |
WO2007037833A3 (en) | 2007-06-14 |
BRPI0616037B1 (pt) | 2018-05-02 |
EP1945719B1 (en) | 2018-07-18 |
EP1945719A2 (en) | 2008-07-23 |
BRPI0616037A2 (pt) | 2011-06-07 |
TW200718723A (en) | 2007-05-16 |
KR101404118B1 (ko) | 2014-06-19 |
NO20081346L (no) | 2008-05-27 |
JP5241497B2 (ja) | 2013-07-17 |
AU2006295289A1 (en) | 2007-04-05 |
WO2007037833A2 (en) | 2007-04-05 |
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