JP4870336B2 - 動的耐久性を改善したシーリング材 - Google Patents
動的耐久性を改善したシーリング材Info
- Publication number
- JP4870336B2 JP4870336B2 JP2004122122A JP2004122122A JP4870336B2 JP 4870336 B2 JP4870336 B2 JP 4870336B2 JP 2004122122 A JP2004122122 A JP 2004122122A JP 2004122122 A JP2004122122 A JP 2004122122A JP 4870336 B2 JP4870336 B2 JP 4870336B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- weight
- parts
- polymer
- reactive silicon
- 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.)
- Expired - Lifetime
Links
- 239000003566 sealing material Substances 0.000 title claims description 11
- 229920000642 polymer Polymers 0.000 claims description 81
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 62
- 239000003054 catalyst Substances 0.000 claims description 44
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 44
- 239000004014 plasticizer Substances 0.000 claims description 18
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 239000000565 sealant Substances 0.000 claims description 11
- 239000000945 filler Substances 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 9
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 claims description 4
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims description 4
- 150000003606 tin compounds Chemical class 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 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 claims description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 3
- -1 polyoxypropylene Polymers 0.000 description 55
- 239000000203 mixture Substances 0.000 description 33
- 150000001875 compounds Chemical class 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 25
- 238000000034 method Methods 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000178 monomer Substances 0.000 description 20
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 229920001451 polypropylene glycol Polymers 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 238000006459 hydrosilylation reaction Methods 0.000 description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 150000002009 diols Chemical class 0.000 description 9
- 150000004756 silanes Chemical class 0.000 description 9
- 239000006087 Silane Coupling Agent Substances 0.000 description 8
- 229910000019 calcium carbonate Inorganic materials 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 239000004793 Polystyrene Substances 0.000 description 7
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 7
- 229920002223 polystyrene Polymers 0.000 description 7
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- XYYQWMDBQFSCPB-UHFFFAOYSA-N dimethoxymethylsilane Chemical compound COC([SiH3])OC XYYQWMDBQFSCPB-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- 239000004611 light stabiliser Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 230000006835 compression Effects 0.000 description 5
- 238000007906 compression Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 230000000379 polymerizing effect Effects 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 4
- 239000012964 benzotriazole Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 4
- 238000009661 fatigue test Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 4
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 4
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 3
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- RRDGKBOYQLLJSW-UHFFFAOYSA-N bis(2-ethylhexyl) 7-oxabicyclo[4.1.0]heptane-3,4-dicarboxylate Chemical compound C1C(C(=O)OCC(CC)CCCC)C(C(=O)OCC(CC)CCCC)CC2OC21 RRDGKBOYQLLJSW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical class OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000000944 linseed oil Substances 0.000 description 3
- 235000021388 linseed oil Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000004570 mortar (masonry) Substances 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000007665 sagging Methods 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000004590 silicone sealant Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- MBNRBJNIYVXSQV-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propane-1-thiol Chemical compound CCO[Si](C)(OCC)CCCS MBNRBJNIYVXSQV-UHFFFAOYSA-N 0.000 description 2
- NNTRMVRTACZZIO-UHFFFAOYSA-N 3-isocyanatopropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCN=C=O NNTRMVRTACZZIO-UHFFFAOYSA-N 0.000 description 2
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-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
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
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- 230000002378 acidificating effect Effects 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
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- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
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- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
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- 239000010941 cobalt Substances 0.000 description 2
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- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- JQCXWCOOWVGKMT-UHFFFAOYSA-N diheptyl phthalate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 2
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920001083 polybutene Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
- C09K3/1018—Macromolecular compounds having one or more carbon-to-silicon linkages
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0016—Plasticisers
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
Description
建築用途に使用する硬化性組成物に対する要求物性は様々であるが、ワーキング目地への使用に際しては、シーラントの動的耐久性が重要視される。
数平均分子量が20,000〜50,000であり1分子中に平均して0.8個以上の反応性ケイ素基を有するオキシアルキレン系重合体(A)、前記重合体(A)の100重量部に対して10重量部を超える可塑剤(B)、充填剤(C)、および硬化触媒(D)を含有することを特徴とする動的耐久性を改善したシーリング材である。
−(SiR1 2-bXbO)m−SiR2 3-aXa (1)
(式中R1およびR2は同一または異なった炭素数1から20のアルキル基、炭素数6から20のアリール基、炭素数7から20のアラルキル基または(R’)3SiO−で示されるトリオルガノシロキシ基を示し、R1またはR2が二個以上存在するとき、それらは同一であってもよく、異なっていてもよい。ここでR’は炭素数1から20の一価の炭化水素基または炭素数6〜20のアリール基であり3個のR’は同一であってもよく、異なっていてもよい。Xは水酸基または加水分解性基を示し、Xが二個以上存在する時、それらは同一であってもよく、異なっていてもよい。aは0、1、2または3を、bは0、1、または2をそれぞれ示す。またm個の(SiR1 2-bXbO)基におけるbについて、それらは同一であってもよく、異なっていてもよい。mは0から19の整数を示す。但し、a+Σb≧1を満足するものとする)で表される基があげられる。
−SiR2 3-aXa (2)
(式中、R2、Xは前記と同じ。aは1〜3の整数)で表される反応性ケイ素基が、入手が容易であるので好ましい。
CH2=C(R3)COOR4・・・(3)
(式中R3は水素原子またはメチル基、R4は炭素数1から9のアルキル基を示す)
CH2=C(R3)COOR5・・・(4)
(式中R3は前記に同じ。R5は炭素数10以上のアルキル基を示す)
CH2=C(R3)COOR6−[Si(R1 2-b)(Xb)O]mSi(R2 3-a)Xa・・・(5)
(式中R3は前記に同じ。R6は炭素数1〜6の2価のアルキレン基を示す。R1,R2,X,a,b,mは式(1)における定義と同じ。)
前記一般式(3)のR4としては、例えばメチル基、エチル基、プロピル基、n−ブチル基、t−ブチル基、2ーエチルヘキシル基などの炭素数1〜8、好ましくは1〜4、さらに好ましくは1〜2のアルキル基を挙げることができる。なお一般式(3)で表されるモノマーは1種類でもよく、2種以上用いてもよい。
ポリケイ皮酸ビニル類としては、シンナモイル基を感光基とする感光性樹脂でありポリビニルアルコールをケイ皮酸でエステル化したものの他、多くのポリケイ皮酸ビニル誘導体が例示される。アジド化樹脂は、アジド基を感光基とする感光性樹脂として知られており、通常はジアジド化合物を感光剤として加えたゴム感光液の他、「感光性樹脂」(昭和47年3月17日出版、印刷学会出版部発行、第93頁〜、第106頁〜、第117頁〜)に詳細な例示があり、これらを単独又は混合し、必要に応じて増感剤を加えて使用することができる。なお、ケトン類、ニトロ化合物などの増感剤やアミン類などの促進剤を添加すると、効果が高められる場合がある。光硬化性物質は反応性ケイ素基を有するオキシプロピレン重合体(A)100重量部に対して0.1〜20重量部、好ましくは0.5〜10重量部の範囲で使用するのがよく、0.1重量部以下では耐候性を高める効果はなく、20重量部以上では硬化物が硬くなりすぎて、ヒビ割れを生じるため好ましくない。
数平均分子量2000のポリオキシプロピレンジオールを開始剤として、複合金属シアン化物錯体を触媒として用いて、プロピレンオキシドを重合することにより数平均分子量37000(GPCより求めたポリスチレン換算値)のポリオキシプロピレンジオールを得た。ナトリウムメチラートの30%メタノール溶液2重量部を加えた後、130℃でメタノールが回収されなくなるまで減圧脱揮を行った。ついでアリルクロライド1.3重量部を加え5時間反応をさせた後、未反応のアリルクロライドを減圧脱揮により除去した後、ヘキサンと水により精製し、1分子中に概ね2個のアリル末端基を含有するオキシプロピレン重合体(P1)を得た。
数平均分子量2000のポリオキシプロピレンジオールを開始剤として、複合金属シアン化物錯体を触媒として用いて、プロピレンオキシドを重合することにより数平均分子量30200(GPCより求めたポリスチレン換算値)、分子量分布1.2のポリオキシプロピレンジオールを得た。ナトリウムメチラートの30%メタノール溶液2.5重量部を加えた後、130℃でメタノールが回収されなくなるまで減圧脱揮を行った。ついでアリルクロライド1.5重量部を加え5時間反応をさせた後、未反応のアリルクロライドを減圧脱揮により除去した後、ヘキサンと水により精製し、1分子中に概ね2個のアリル末端基を含有するオキシプロピレン重合体(P2)を得た。
。
数平均分子量2000のポリオキシプロピレンジオールを開始剤として、複合金属シアン化物錯体を触媒として用いて、プロピレンオキシドを重合することにより数平均分子量19000(GPCより求めたポリスチレン換算値)、分子量分布1.1のポリオキシプロピレンジオールを得た。ナトリウムメチラートの30%メタノール溶液4.2重量部を加えた後、130℃でメタノールが回収されなくなるまで減圧脱揮を行った。ついでアリルクロライド2.8重量部を加え5時間反応をさせた後、未反応のアリルクロライドを減圧脱揮により除去した後、ヘキサンと水により精製し、1分子中に概ね2個のアリル末端基を含有するオキシプロピレン重合体(P3)を得た。
合成例1で得たP1のアリル基1モルに対してジメトキシメチルシラン0.65モルを塩化白金酸の存在下反応させて、分子末端にジメトキシメチルシリル基を有するオキシプロピレン重合体(P4)を得た。
合成例1で得たP1のアリル基1モルに対してジメトキシメチルシラン0.50モルを塩化白金酸の存在下反応させて、分子末端にジメトキシメチルシリル基を有するオキシプロピレン重合体(P5)を得た。
合成例1で得たP1のアリル基1モルに対してジメトキシメチルシラン0.40モルを塩化白金酸の存在下反応させて、分子末端にジメトキシメチルシリル基を有するオキシプロピレン重合体(P6)を得た。
合成例1で得たP1のアリル基1モルに対してジメトキシメチルシラン0.30モルを塩化白金酸の存在下反応させて、分子末端にジメトキシメチルシリル基を有するオキシプロピレン重合体(P7)を得た。
合成例2で得たP2のアリル基1モルに対してジメトキシメチルシラン0.65モルを塩化白金酸の存在下反応させて、分子末端にジメトキシメチルシリル基を有するオキシプロピレン重合体(P8)を得た。
合成例3で得たP3のアリル基1モルに対してジメトキシメチルシラン0.65モルを塩化白金酸の存在下反応させて、分子末端にジメトキシメチルシリル基を有するオキシプロピレン重合体(P9)を得た。
数平均分子量2000のポリオキシプロピレンジオールを開始剤として、複合金属シアン化物錯体触媒として用いて、プロピレンオキシドを重合することにより数平均分子量37000(GPCより求めたポリスチレン換算値)のポリオキシプロピレンジオールを得た。得られたポリプロピレングリコールの水酸基1モルに対してγ−イソシアネートプロピルトリメトキシシラン0.65モルを加えてウレタン化反応を行い、分子末端にトリメトキシシリル基を有するオキシプロピレン重合体(P10)を得た。
反応性ケイ素基含有オキシアルキレン系重合体として合成例4で得られたP4を100重量部、可塑剤としてジイソデシルフタレート60重量部、充填剤として炭酸カルシウム120重量部、硬化触媒としてジブチルスズビスアセチルアセトナート1重量部、及び酸化チタン20重量部、ポリアミドワックス2重量部、ビニルトリメトキシシラン2重量部、N−(β−アミノエチル)−γ−アミノプロピルトリメトキシシラン3重量部を充分に混錬して1液型硬化性組成物を作成し、カートリッジに充填し下記の試験を実施した。
厚さ3mmのシートを作製し、23℃湿度60%で3日間養生により硬化させ、更に50℃オーブンで4日間養生し、室温に戻した後、JIS3号ダンベルを打ち抜き、引張り速度200mm/minにおける300%伸張時応力(M300)、及び破断時伸びをオートグラフで測定した。
アルミ基材を使用し、ASTMC719テストサンプルを作製。70℃で50%圧縮を7日間行い、室温開放して1日後のサンプルの復元率を測定した。
(サンプル準備)
モルタル基材を使用し、n=3で測定。
モルタル用プライマーを塗布後シーラントを施工し、硬化養生。(目地幅=1/2inch)
70℃50%圧縮を一週間経てからサイクル試験に移る。
(サイクル試験)
100%伸長と50%圧縮を1サイクルとし室温で10サイクル試験を行う。(目地の動くスピード=1/8(inch/hr))
次ぎにヒートサイクル試験(70℃下で50%圧縮後、−26℃下で100%伸長)を10サイクル行う。
試験後サンプルを確認し、剥離もしくは凝集破壊の面積がサンプル全体(n=3)の50%以下なら合格(=○)とし、これ以外を不合格(=×)とする。
カートリッジからの押しだし性と、各種サンプルの作製状況から判定した。
反応性ケイ素基含有オキシアルキレン系重合体として合成例8で得られたP8を100重量部用いることを除いては、実施例1と同様の方法で硬化性組成物を作成し、同様の評価を行った。
反応性ケイ素基含有オキシアルキレン系重合体として合成例5で得られたP5を100重量部用いることを除いては、実施例1と同様の方法で硬化性組成物を作成し、同様の評価を行った。
反応性ケイ素基含有オキシアルキレン系重合体として合成例6で得られたP6を100重量部用いることを除いては、実施例1と同様の方法で硬化性組成物を作成し、同様の評価を行った。
反応性ケイ素基含有オキシアルキレン系重合体として合成例10で得られたP10を100重量部用い、硬化触媒としてジブチルスズジラウレートを0.1重量部用いることを除いては、実施例1と同様の方法で硬化性組成物を作成し、同様の評価を行った。
可塑剤を使用しないことを除いては、実施例1と同様の方法で硬化性組成物を作成し、同様の評価を行った。
反応性ケイ素基含有オキシアルキレン系重合体として合成例7で得られたP7を100重量部用いることを除いては、実施例1と同様の方法で硬化性組成物を作成し、同様の評価を行った。
反応性ケイ素基含有オキシアルキレン系重合体として合成例9で得られたP9を100重量部用いることを除いては、実施例1と同様の方法で硬化性組成物を作成し、同様の評価を行った。
Claims (3)
- 数平均分子量が20,000〜50,000であり1分子中に平均して0.8個以上1.3個以下の反応性ケイ素基を有するオキシアルキレン系重合体(A)、前記重合体(A)の100重量部に対して10重量部を超え300重量部以下の可塑剤(B)、1〜200重量部の充填剤(C)、および0.01〜20重量部の4価のスズ化合物(D)を含有するシーリング材であって、
ここで、オキシアルキレン系重合体(A)の主鎖骨格は、開始剤と触媒の存在下、モノエポキシドを開環重合することによって得られ、該開始剤は2価アルコールであり、該モノエポキシドは、アルキレンオキシドである、シーリング材。 - 前記重合体(A)の主鎖骨格を得る際の前記触媒が複合金属シアン化物錯体触媒である請求項1記載のシーリング材。
- 前記4価のスズ化合物(D)が、ジブチルスズビスアセチルアセトナートまたはジブチルスズジラウレートのいずれかである、請求項1または2記載のシーリング材。
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JP2004122122A JP4870336B2 (ja) | 2004-04-16 | 2004-04-16 | 動的耐久性を改善したシーリング材 |
US11/101,576 US7294669B2 (en) | 2004-04-16 | 2005-04-08 | Sealant having improved dynamic durability |
EP05008194A EP1586597A1 (en) | 2004-04-16 | 2005-04-14 | Sealant having improved dynamic durability |
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DE102009022631A1 (de) * | 2009-05-25 | 2010-12-16 | Evonik Goldschmidt Gmbh | Härtbare Silylgruppen enthaltende Zusammensetzungen und deren Verwendung |
JP2014024989A (ja) * | 2012-07-27 | 2014-02-06 | Asahi Glass Co Ltd | 加水分解性ケイ素基を有する重合体の製造方法 |
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JPH051225A (ja) * | 1991-06-25 | 1993-01-08 | Kanegafuchi Chem Ind Co Ltd | 硬化性組成物 |
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