JP5648888B2 - 耐熱性が改善された硬化性組成物 - Google Patents
耐熱性が改善された硬化性組成物 Download PDFInfo
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- JP5648888B2 JP5648888B2 JP2009287285A JP2009287285A JP5648888B2 JP 5648888 B2 JP5648888 B2 JP 5648888B2 JP 2009287285 A JP2009287285 A JP 2009287285A JP 2009287285 A JP2009287285 A JP 2009287285A JP 5648888 B2 JP5648888 B2 JP 5648888B2
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- oxide
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- 239000000203 mixture Substances 0.000 title claims description 60
- 229920000642 polymer Polymers 0.000 claims description 114
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 105
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 65
- -1 trimethoxysilyl group Chemical group 0.000 claims description 49
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 32
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 32
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 30
- 239000000292 calcium oxide Substances 0.000 claims description 30
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 23
- 239000000395 magnesium oxide Substances 0.000 claims description 22
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 10
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 238000004132 cross linking Methods 0.000 claims description 4
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 claims 1
- 239000000853 adhesive Substances 0.000 description 41
- 230000001070 adhesive effect Effects 0.000 description 40
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- 230000000052 comparative effect Effects 0.000 description 23
- 239000003054 catalyst Substances 0.000 description 21
- 238000000034 method Methods 0.000 description 16
- 239000000178 monomer Substances 0.000 description 16
- 239000003566 sealing material Substances 0.000 description 16
- 229920001451 polypropylene glycol Polymers 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 239000000945 filler Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
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- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000004014 plasticizer Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
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- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical class C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003945 anionic surfactant Substances 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000013008 thixotropic agent Substances 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 150000004756 silanes Chemical class 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 5
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 5
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
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- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 4
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- NXMOWTFIUDDXIT-UHFFFAOYSA-L [7,7-dimethyloctanoyloxy(dioctyl)stannyl] 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCC(C)(C)C NXMOWTFIUDDXIT-UHFFFAOYSA-L 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000000440 bentonite Substances 0.000 description 3
- 229910000278 bentonite Inorganic materials 0.000 description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 125000005702 oxyalkylene group Chemical group 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000007665 sagging Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000012756 surface treatment agent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 3
- TYKCBTYOMAUNLH-MTOQALJVSA-J (z)-4-oxopent-2-en-2-olate;titanium(4+) Chemical compound [Ti+4].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O TYKCBTYOMAUNLH-MTOQALJVSA-J 0.000 description 2
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-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
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical group CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 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
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
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- 239000007788 liquid Substances 0.000 description 1
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- 239000003607 modifier 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
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- JFOJYGMDZRCSPA-UHFFFAOYSA-J octadecanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O JFOJYGMDZRCSPA-UHFFFAOYSA-J 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical group C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- BPJZKLBPJBMLQG-KWRJMZDGSA-N propanoyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC(=O)CC BPJZKLBPJBMLQG-KWRJMZDGSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- FZHCFNGSGGGXEH-UHFFFAOYSA-N ruthenocene Chemical compound [Ru+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 FZHCFNGSGGGXEH-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000009974 thixotropic effect Effects 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- QEEPNARXASYKDD-UHFFFAOYSA-J tris(7,7-dimethyloctanoyloxy)stannyl 7,7-dimethyloctanoate Chemical compound [Sn+4].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O QEEPNARXASYKDD-UHFFFAOYSA-J 0.000 description 1
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- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polyethers (AREA)
Description
(式中、R1は、炭素数1〜20のアルキル基、炭素数3〜20のシクロアルキル基、炭素数6〜20のアリール基、炭素数7〜20のアラルキル基またはR1 3SiO−(R1前期と同じ)で示されるトリオルガノシロキシ基を示し、R1が2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。Xは水酸基または加水分解性基を示し、Xが2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。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n個の式(2):
におけるbは同一である必要はない。nは0〜19の整数を示す。但し、a+(bの和)≧1を満足するものとする。)で表わされる基があげられる。
なお、式(3):
(式中、R1,X,aは前記と同じ)で表わされる架橋性珪素基が、入手が容易である点から好ましい。また、硬度速度が大きい組成物を得るには、式(3)の架橋性珪素基においてaが3である場合が好ましい。
等があげられる。ポリオキシアルキレン系重合体の主鎖骨格は、1種類だけの繰り返し単位からなってもよいし、2種類以上の繰り返し単位からなってもよい。特にオキシプロピレンを主成分とする重合体から成るのが好ましい。
(式中、R3は前記に同じ、R5は炭素数1〜5のアルキル基を示す)
で表される(メタ)アクリル酸エステル単量体単位と、下記式(7):
(式中、R3は前記に同じ、R6は炭素数6以上のアルキル基を示す)
で表される(メタ)アクリル酸エステル単量体単位からなる共重合体であることが好ましい。
ポリオキシプロピレンジオールにナトリウムメトキシド(NaOMe)のメタノール溶液を添加してメタノールを留去し、更に塩化アリルを添加して末端の水酸基をアリル基に変換した。未反応の塩化アリルを減圧脱揮により除去し、さらに生成した金属塩を水により抽出除去して、末端にアリル基を有するポリオキシプロピレンを得た。得られたアリル基末端ポリオキシプロピレンに対し、白金ビニルシロキサン錯体のイソプロパノール溶液を添加し、トリメトキシシランを反応させ、PPG(ポリプロピレングリコール)換算の重量平均分子量が約25000、1分子当たり1.5個の末端トリメトキシシリル基を有するポリオキシプロピレン系重合体を得た。
合成例1で用いたポリオキシプロピレンジオールより分子量が小さいポリオキシプロピレンジオールにナトリウムメトキシド(NaOMe)のメタノール溶液を添加してメタノールを留去し、更に塩化アリルを添加して末端の水酸基をアリル基に変換した。未反応の塩化アリルを減圧脱揮により除去し、さらに生成した金属塩を水により抽出除去して、末端にアリル基を有するポリオキシプロピレンを得た。得られたアリル基末端ポリオキシプロピレンに対し、白金ビニルシロキサン錯体のイソプロパノール溶液を添加し、トリメトキシシランを反応させ、PPG換算の重量平均分子量が約15000、1分子当たり1.5個の末端トリメトキシシリル基を有するポリオキシプロピレン系重合体を得た。
フラスコに溶剤である酢酸エチル40重量部、メチルメタクリレート59重量部、2−エチルヘキシルメタクリレート25重量部、γ−メタクリロキシプロピルトリメトキシシラン22重量部、及び金属触媒としてルテノセンジクロライド0.1重量部を仕込み窒素ガスを導入しながら80℃に加熱した。ついで、3−メルカプトプロピルトリメトキシシラン8重量部をフラスコ内に添加し80℃で6時間反応を行った。室温に冷却後、ベンゾキノン溶液(95%THF溶液)を20重量部添加して重合を停止した。溶剤および未反応物を留去し、ポリスチレン換算の重量平均分子量が約6000であるトリメトキシシリル基を有するアクリル酸エステル系重合体を得た。
硬化速度は皮張り時間によって評価した。内径60mmの円筒容器に5mm厚まで試料を充填し、直ちに23℃、50%RHの恒温恒湿室に静置し、表面を指で触り、組成物が指に付着しなくなるまでの時間を測定する。
幅25mm、長さ100mm、厚み1.6mmのアルミ板に、接着剤組成物を一端から75mmの長さの部分に200μmの厚みに塗布する。一方、幅25mm、長さ200mmの5号キャンパスに、接着剤組成物を一端から75mmの長さの部分に200μmの厚みに2回塗布する。塗布部分が重なるように貼り合わせ、ハンドローラーで3往復厚締する。これを23℃50%RHで1週間養生したものを試験片とする。所定温度雰囲気下でキャンパスの180°剥離強度を測定する(引張りスピード200mm/分)。
JIS K6253に準拠し、接着剤組成物の23℃、50%RHで1週間養生したものを試験片とし、JIS A硬度を測定する。
接着剤から厚み2mmのシートを調製する。動的粘弾性試験は、セイコーインスツルメンツ(株)製DMS6100を用いて、測定温度23℃、周波数100Hz及び歪率0.1%の条件で、2mmシートについて行い、次に損失正接(tanδ)を下式により求める。
tanδ=E”/E’
(E’:貯蔵弾性率、E”:損失弾性率)
内径60mmの円筒容器に50mm厚まで試料を充填し、外径4mmのガラス棒の先端40mmを試料に垂直に沈める。直ちにガラス棒を静かに引き上げ、試料の糸切れ性を確認した。評価基準は、○:糸切れする、△:少し糸引きする、×:糸引きする。
酸化防止剤:チバ・ジャパン(株)製、ヒンダードフェノール系酸化防止剤、商品名:イルガノックス245、1重量部。
脱水剤:コルコート(株)製、テトラエトキシシラン、商品名:エチルシリケート28、1重量部。
希釈剤:ジャパンエナジー(株)製、パラフィン系希釈剤、商品名:カクタスノルマルパラフィンN−11、10重量部。
接着性付与剤:信越化学工業(株)製、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、商品名:信越シリコーンKBM603、6重量部。
実施例1〜2及び比較例1〜2においては、架橋性珪素基としてトリアルコキシシリル基を有するポリオキシアルキレン系重合体を使用している。接着剤の硬化速度、熱間剥離強度、硬度、損失正接および糸切れ性を表1に示した。実施例1〜2と比較例1との比較から明らかなように、炭酸カルシウムに代えて酸化カルシウムを添加することにより、剥離強度、特に、高温時の剥離強度が改善されることがわかる。また、硬度が大きくなることがわかる。なお、実施例1〜2、比較例1においては酸化カルシウムと炭酸カルシウムの合計量が同一になるよう組成物を調製している。また、実施例1と、同様の組成で充填剤を配合していない組成物(比較例2)の糸切れ性を比較したところ、実施例1の糸切れ性は○であったが、充填剤を配合していない組成物(比較例2)の糸切れ性は×であった。
参考例1、参考比較例1においては、架橋性珪素基としてトリアルコキシシリル基に代えて市販されているジアルコキシシリル基を有する重合体を使用している。接着剤の硬化速度、熱間剥離強度、硬度および損失正接を表1に示した。参考例1と参考比較例1との比較から明らかなように、この重合体を使用した場合にも炭酸カルシウムに代えて酸化カルシウムを添加することにより、剥離強度、特に、高温時の剥離強度が改善されることがわかる。また、硬度が大きくなることがわかる。架橋性珪素基としてジアルコキシシリル基を有する重合体を用いた硬化性組成物はトリアルコキシシリル基を有する重合体を用いた硬化性組成物よりも硬化速度が小さいので活性が高い硬化触媒を使用している。また、ジアルコキシシリル基を有する重合体を用いた硬化性組成物はトリアルコキシシリル基を有する重合体を用いた硬化性組成物よりも剥離強度が大きくなる傾向にある。
実施例3〜10及び比較例3〜4においては、架橋性珪素基を有するポリオキシアルキレン系重合体として合成例1で得られた重合体と合成例2で得られた重合体とを混合して使用している。また、実施例3〜7では酸化カルシウム(表面処理されたものを含む)を使用し、実施例8〜10では酸化マグネシウム(表面処理されたものを含む)を使用している。比較例4では金属酸化物である酸化チタンを使用している。接着剤の硬化速度、熱間剥離強度、硬度および損失正接を表2に示した。
実施例11及び比較例5においては、架橋性珪素基を有するポリオキシアルキレン系重合体として合成例1で得られた重合体と合成例2で得られた重合体とを混合して使用しているが、合成例2で得られた分子量が小さい重合体を増量して使用している。接着剤の硬化速度、熱間剥離強度、硬度および損失正接を表3に示した。
実施例12〜13、比較例6においては、硬化触媒としてジオクチル錫ジバーサテートにかえてジオクチル錫オキシドを使用した。但し、ジオクチル錫オキシドは触媒活性が低く、触媒活性を向上させるため接着剤組成物の製造後、接着剤組成物の加熱処理を行った。接着剤の硬化速度、熱間剥離強度、硬度および損失正接を表3に示した。実施例12〜13と比較例5との比較から明らかなように、他の触媒を用いても炭酸カルシウムに代えて酸化カルシウムを添加することにより、高温時の剥離強度や硬度が改善されることがわかる。
*1:(株)カネカ製、主鎖がポリオキシプロピレンで分子末端にジメトキシ基を有するポリマーと、主鎖がポリメタクリル酸エステルの共重合体で分子中にジメトキシシリル基を有するポリマーとの混合物、商品名:サイリルMA440
*2:近江化学(株)製、表面処理されていない酸化カルシウム、商品名:CML−35S
*3:近江化学(株)製、脂肪酸処理酸化カルシウム、商品名:CML−31
*4:神島化学(株)製、表面処理されていない酸化マグネシウム、商品名:スターマグM
*5:神島化学(株)製、脂肪酸処理酸化マグネシウム、商品名:スターマグCX
*6:堺化学工業(株)製、表面処理されていないルチル型酸化チタン、商品名:DAIAWHITE TCR−10
*7:白石カルシウム(株)製、重質炭酸カルシウム、商品名:ホワイトンSB
*8:丸尾カルシウム(株)製、脂肪酸処理炭酸カルシウム、商品名:カルファイン200
*9:日東化成(株)製、ジオクチル錫ジバーサテート硬化触媒、商品名:ネオスタン U−830
*10:日東化成(株)製、ジオクチル錫オキシド硬化触媒、商品名:ネオスタン U−800P
*11:日東化成(株)製、ジブチル錫ビスアセチルアセトナート硬化触媒、商品名:ネオスタン U−220H
Claims (2)
- 珪素原子に結合した水酸基又は加水分解性基を有し、シロキサン結合を形成し架橋し得る架橋性珪素基を分子鎖末端に有するポリオキシアルキレン系重合体、該ポリオキシアルキレン系重合体100重量部に対し珪素原子に結合した水酸基又は加水分解性基を有し、湿分によりシロキサン結合を形成することによって架橋し得る架橋性珪素基を有する(メタ)アクリル酸エステル重合体10〜200重量部、膠質炭酸カルシウム及び酸化カルシウムと酸化マグネシウムからなる群から選択される少なくとも1種の酸化物を含有する硬化性組成物であって、該架橋性珪素基がトリメトキシシリル基であり、すべての架橋性珪素基を有する重合体100重量部、に対して膠質炭酸カルシウム2〜200重量部、及び酸化カルシウムと酸化マグネシウムからなる群から選択される少なくとも1種の酸化物を2〜100重量部含有する硬化性組成物。
- 酸化カルシウムと酸化マグネシウムからなる群から選択される少なくとも1つの酸化物が表面処理されていない酸化物であることを特徴とする請求項1記載の硬化性組成物。
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