JPWO2016035718A1 - 硬化性組成物 - Google Patents
硬化性組成物 Download PDFInfo
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- JPWO2016035718A1 JPWO2016035718A1 JP2016546622A JP2016546622A JPWO2016035718A1 JP WO2016035718 A1 JPWO2016035718 A1 JP WO2016035718A1 JP 2016546622 A JP2016546622 A JP 2016546622A JP 2016546622 A JP2016546622 A JP 2016546622A JP WO2016035718 A1 JPWO2016035718 A1 JP WO2016035718A1
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- polymer
- meth
- weight
- acrylic acid
- Prior art date
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- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 131
- 229920000642 polymer Polymers 0.000 claims abstract description 222
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 100
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 93
- 229920000620 organic polymer Polymers 0.000 claims abstract description 50
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 32
- 150000001451 organic peroxides Chemical class 0.000 claims abstract description 12
- -1 acrylate ester Chemical class 0.000 claims description 143
- 238000000034 method Methods 0.000 claims description 62
- 125000004432 carbon atom Chemical group C* 0.000 claims description 59
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000000524 functional group Chemical group 0.000 claims description 29
- 229910052710 silicon Inorganic materials 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 239000010703 silicon Substances 0.000 claims description 25
- 150000002148 esters Chemical class 0.000 claims description 23
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 16
- 125000002723 alicyclic group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 229920000058 polyacrylate Polymers 0.000 claims description 14
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 12
- 239000004793 Polystyrene Substances 0.000 claims description 11
- 239000003999 initiator Substances 0.000 claims description 11
- 229920002223 polystyrene Polymers 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 7
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 7
- 229920006222 acrylic ester polymer Polymers 0.000 claims description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 239000003505 polymerization initiator Substances 0.000 abstract description 15
- 150000002825 nitriles Chemical class 0.000 abstract description 10
- 239000007869 azo polymerization initiator Substances 0.000 abstract description 9
- 239000007870 radical polymerization initiator Substances 0.000 abstract description 4
- 239000000178 monomer Substances 0.000 description 62
- 229940048053 acrylate Drugs 0.000 description 60
- 239000000047 product Substances 0.000 description 59
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 53
- 150000001875 compounds Chemical class 0.000 description 50
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 34
- 239000000463 material Substances 0.000 description 33
- 239000004014 plasticizer Substances 0.000 description 31
- 239000000853 adhesive Substances 0.000 description 30
- 239000000126 substance Substances 0.000 description 29
- 230000001070 adhesive effect Effects 0.000 description 28
- 239000003795 chemical substances by application Substances 0.000 description 28
- 229920001451 polypropylene glycol Polymers 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 229920002554 vinyl polymer Polymers 0.000 description 23
- 239000003566 sealing material Substances 0.000 description 22
- 238000002156 mixing Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 229910000019 calcium carbonate Inorganic materials 0.000 description 17
- 229920001577 copolymer Polymers 0.000 description 17
- 150000002430 hydrocarbons Chemical group 0.000 description 17
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 17
- 230000000704 physical effect Effects 0.000 description 17
- 238000009826 distribution Methods 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000001723 curing Methods 0.000 description 15
- 150000004756 silanes Chemical class 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 13
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 12
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 239000004611 light stabiliser Substances 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 229920005862 polyol Polymers 0.000 description 12
- 150000003077 polyols Chemical class 0.000 description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 11
- XYYQWMDBQFSCPB-UHFFFAOYSA-N dimethoxymethylsilane Chemical compound COC([SiH3])OC XYYQWMDBQFSCPB-UHFFFAOYSA-N 0.000 description 11
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 11
- 238000010526 radical polymerization reaction Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 10
- 239000000945 filler Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- 229920000570 polyether Polymers 0.000 description 10
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 230000018044 dehydration Effects 0.000 description 9
- 238000006297 dehydration reaction Methods 0.000 description 9
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 238000005119 centrifugation Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000002243 precursor Substances 0.000 description 8
- 150000003377 silicon compounds Chemical class 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 7
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 7
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 7
- 125000003700 epoxy group Chemical group 0.000 description 7
- 239000003822 epoxy resin Substances 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- 229920001228 polyisocyanate Polymers 0.000 description 7
- 239000005056 polyisocyanate Substances 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 239000005060 rubber Substances 0.000 description 6
- 239000000565 sealant Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- KHLRJDNGHBXOSV-UHFFFAOYSA-N 5-trimethoxysilylpentane-1,3-diamine Chemical compound CO[Si](OC)(OC)CCC(N)CCN KHLRJDNGHBXOSV-UHFFFAOYSA-N 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 239000006087 Silane Coupling Agent Substances 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 235000006708 antioxidants Nutrition 0.000 description 5
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 5
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- 238000010276 construction Methods 0.000 description 5
- 239000012024 dehydrating agents Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
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- 239000003607 modifier Substances 0.000 description 5
- 125000005702 oxyalkylene group Chemical group 0.000 description 5
- 229920002857 polybutadiene Polymers 0.000 description 5
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- 239000000377 silicon dioxide Substances 0.000 description 5
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- 239000013008 thixotropic agent Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 4
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 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
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 4
- ZUMQLFHCCNIEAO-UHFFFAOYSA-N bis(ethenyl)-silyloxysilane platinum Chemical compound [Pt].[SiH3]O[SiH](C=C)C=C ZUMQLFHCCNIEAO-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 4
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 230000001771 impaired effect Effects 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 229940035429 isobutyl alcohol Drugs 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 4
- 239000013500 performance material Substances 0.000 description 4
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000012643 polycondensation polymerization Methods 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
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- 150000003839 salts Chemical class 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 4
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 4
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 4
- AAPLIUHOKVUFCC-UHFFFAOYSA-N trimethylsilanol Chemical compound C[Si](C)(C)O AAPLIUHOKVUFCC-UHFFFAOYSA-N 0.000 description 4
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
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- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- IFXDUNDBQDXPQZ-UHFFFAOYSA-N 2-methylbutan-2-yl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CC IFXDUNDBQDXPQZ-UHFFFAOYSA-N 0.000 description 3
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 3
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 3
- NFWPZNNZUCPLAX-UHFFFAOYSA-N 4-methoxy-3-methylaniline Chemical compound COC1=CC=C(N)C=C1C NFWPZNNZUCPLAX-UHFFFAOYSA-N 0.000 description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- 238000006845 Michael addition reaction Methods 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- 229920002367 Polyisobutene Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- 238000004382 potting Methods 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000010734 process oil Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BYOIQYHAYWYSCZ-UHFFFAOYSA-N prop-2-enoxysilane Chemical compound [SiH3]OCC=C BYOIQYHAYWYSCZ-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 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
- JTQPTNQXCUMDRK-UHFFFAOYSA-N propan-2-olate;titanium(2+) Chemical compound CC(C)O[Ti]OC(C)C JTQPTNQXCUMDRK-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 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
- KOPQZJAYZFAPBC-UHFFFAOYSA-N propanoyl propaneperoxoate Chemical compound CCC(=O)OOC(=O)CC KOPQZJAYZFAPBC-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006298 saran Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000005371 silicon functional group Chemical group 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- ACECBHHKGNTVPB-UHFFFAOYSA-N silylformic acid Chemical class OC([SiH3])=O ACECBHHKGNTVPB-UHFFFAOYSA-N 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000600 sorbitol Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000006557 surface reaction Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 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
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- XSIGLRIVXRKQRA-UHFFFAOYSA-N triethoxysilylmethanethiol Chemical compound CCO[Si](CS)(OCC)OCC XSIGLRIVXRKQRA-UHFFFAOYSA-N 0.000 description 1
- QYBKVVRRGQSGDC-UHFFFAOYSA-N triethyl methyl silicate Chemical compound CCO[Si](OC)(OCC)OCC QYBKVVRRGQSGDC-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 1
- ARKBFSWVHXKMSD-UHFFFAOYSA-N trimethoxysilylmethanamine Chemical compound CO[Si](CN)(OC)OC ARKBFSWVHXKMSD-UHFFFAOYSA-N 0.000 description 1
- QJOOZNCPHALTKK-UHFFFAOYSA-N trimethoxysilylmethanethiol Chemical compound CO[Si](CS)(OC)OC QJOOZNCPHALTKK-UHFFFAOYSA-N 0.000 description 1
- 235000021081 unsaturated fats Nutrition 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
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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
- C08L47/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Compositions of derivatives of such polymers
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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
- C08L59/00—Compositions of polyacetals; Compositions of derivatives of polyacetals
- C08L59/02—Polyacetals containing polyoxymethylene sequences only
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
- C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
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- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Sealing Material Composition (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyethers (AREA)
Abstract
Description
(1).
架橋性シリル基を含有する(メタ)アクリル酸エステルと(メタ)アクリル酸アルキルエステルに由来する繰り返し単位を有する加水分解性ケイ素基含有(メタ)アクリル酸エステル系重合体(A)と、分子鎖末端もしくは分子鎖末端部位のみに架橋性シリル基を有する有機重合体(B)を含有する硬化性組成物であって、(メタ)アクリル酸エステル系重合体(A)が非ニトリル系アゾ系重合開始剤に由来する基を有する硬化性組成物、
(2).
(メタ)アクリル酸エステル系重合体(A)が60℃〜140℃で共重合することで得られる(1)に記載の硬化性組成物、
(3).
(メタ)アクリル酸エステル系重合体(A)の重合法が溶液重合法である(1)または(2)に記載の硬化性組成物、
(4).
有機重合体(B)の主鎖がポリオキシアルキレン系重合体、(メタ)アクリル酸エステル系重合体、および飽和炭化水素系重合体からなる群から選択される1種以上である(1)〜(3)のいずれかに記載の硬化性組成物、
(5).
(メタ)アクリル酸エステル系重合体(A)の重量平均分子量が7000〜14000である(1)〜(4)のいずれかに記載の硬化性組成物、
(6).
(メタ)アクリル酸エステル系重合体(A)が一般式(1):
−SiX3 (1)
(式中、Xはヒドロキシ基または加水分解性基であり、3個のXは同一であっても良く、異なっていてもよい)および/または一般式(2):
−SiR1X2 (2)
(R1は、炭素原子数1から20の置換あるいは非置換のアルキル基、炭素原子数6から20のアリール基、炭素原子数7から20のアラルキル基、または、−OSiR’3(R’は、それぞれ独立に炭素原子数1から20の炭化水素基である)で示されるトリオルガノシロキシ基である。また、Xは前記と同じであり、2個のXは同一であっても良く、異なっていてもよい。)で表されるケイ素含有官能基を1分子中に平均して0.5〜2.5個有し、一般式(1)に示すケイ素含有官能基が1分子中に平均して0〜2.0個、一般式(2)に示すケイ素含有官能基が1分子中に平均して0〜2.0個である(1)〜(5)のいずれかに記載の硬化性組成物、
(7).
(メタ)アクリル酸エステル系重合体(A)が、エステルを構成するアルコール成分が炭素数1〜4の直鎖状、分岐状または脂環式アルキル基のメタクリル酸エステル0〜15重量部、エステルを構成するアルコール成分が炭素数1〜4の直鎖状、分岐状または脂環式アルキル基のアクリル酸エステル55〜90重量部、エステルを構成するアルコール成分が炭素数8以上の直鎖状、分岐状または脂環式アルキル基の(メタ)アクリル酸エステル5〜30重量部に由来する繰り返し単位を有する(1)〜(6)のいずれかに記載の硬化性組成物、
(8).
(メタ)アクリル酸エステル系重合体(A)が、メチルメタクリレート0〜15重量部、ブチルアクリレート55〜90重量部、および2−エチルヘキシルアクリレート5〜30重量部に由来する繰り返し単位を有する(1)〜(7)のいずれかに記載の硬化性組成物、
(9).
架橋性シリル基を含有する(メタ)アクリル酸エステルと(メタ)アクリル酸アルキルエステルに由来する繰り返し単位を有する加水分解性ケイ素基含有(メタ)アクリル酸エステル系重合体(A)と、分子鎖末端もしくは分子鎖末端部位のみに架橋性シリル基を有する有機重合体(B)を含有する硬化性組成物であって、(メタ)アクリル酸エステル系重合体(A)が有機過酸化物系重合開始剤に由来する基を有し、エステルを構成するアルコール成分が炭素数1〜4の直鎖状、分岐状または脂環式アルキル基のメタクリル酸エステル0〜15重量部、エステルを構成するアルコール成分が炭素数1〜4の直鎖状、分岐状または脂環式アルキル基のアクリル酸エステル55〜90重量部、エステルを構成するアルコール成分が炭素数8以上の直鎖状、分岐状または脂環式アルキル基の(メタ)アクリル酸エステル5〜30重量部に由来する繰り返し単位を有し、重量平均分子量が7000〜14000であり、(メタ)アクリル酸エステル系重合体(A)が一般式(1)および/または一般式(2)で表されるケイ素含有官能基を1分子中に平均して0.5〜2.3個有する硬化性組成物、
−SiX3 (1)
(式中、Xはヒドロキシ基または加水分解性基であり、3個のXは同一であっても良く、異なっていてもよい)
−SiR1X2 (2)
(R1は、炭素原子数1から20の置換あるいは非置換のアルキル基、炭素原子数6から20のアリール基、炭素原子数7から20のアラルキル基、または、−OSiR’3(R’は、それぞれ独立に炭素原子数1から20の炭化水素基である)で示されるトリオルガノシロキシ基である。また、Xは前記と同じであり、2個のXは同一であっても良く、異なっていてもよい。)
(10).
有機重合体(B)の主鎖がポリオキシアルキレン系重合体、(メタ)アクリル酸エステル系重合体、および飽和炭化水素系重合体からなる群から選択される1種以上である(9)に記載の硬化性組成物、
(11).
(メタ)アクリル酸エステル系重合体(A)が、一般式(1)に示すケイ素含有官能基を1分子中に平均して0〜2.0個、一般式(2)に示すケイ素含有官能基を1分子中に平均して0〜2.0個有する(9)または(10)に記載の硬化性組成物、
(12).
(メタ)アクリル酸エステル系重合体(A)が、メチルメタクリレート0〜15重量部、ブチルアクリレート55〜90重量部、および2−エチルヘキシルアクリレート5〜30重量部に由来する繰り返し単位を有する(9)〜(11)のいずれかに記載の硬化性組成物、
(13).
(メタ)アクリル酸エステル系重合体(A)の23℃、3°×R14の条件で測定されるE型粘度が15〜200Pa・sである(1)〜(12)のいずれかに記載の硬化性組成物、
(14).
有機重合体(B)に含有される架橋性シリル基が重合体1分子中に平均して0.5個以上、数平均分子量がGPCにおけるポリスチレン換算において800から50,000、有機重合体(B)の架橋性シリル基は、一般式(3):
−SiR2 3−aXa (3)
(R2は、それぞれ独立に炭素原子数1から20の置換あるいは非置換のアルキル基、炭素原子数6から20のアリール基、炭素原子数7から20のアラルキル基、または、−OSiR’3(R’は、それぞれ独立に炭素原子数1から20の炭化水素基である)で示されるトリオルガノシロキシ基である。また、Xは、それぞれ独立にヒドロキシ基または加水分解性基である。更に、aは1から3の整数である)で表される(1)〜(13)のいずれかに記載の硬化性組成物、
に関する。
−SiX3 (1)
(式中、Xはヒドロキシ基または加水分解性基であり、3個のXは同一であっても良く、異なっていてもよい)
−SiR1X2 (2)
(R1は、炭素原子数1から20の置換あるいは非置換のアルキル基、炭素原子数6から20のアリール基、炭素原子数7から20のアラルキル基、または、−OSiR’3(R’は、それぞれ独立に炭素原子数1から20の炭化水素基である)で示されるトリオルガノシロキシ基である。また、Xは前記と同じであり、2個のXは同一であっても良く、異なっていてもよい。)
1分子中のケイ素含有官能基の個数は、GPCによるポリスチレン換算の数平均分子量とケイ素基含有官能基の濃度(モル/g)の積として求められる。また加水分解性基は後に詳述する。
−SiR2 3−aXa (3)
(R2は、それぞれ独立に炭素原子数1から20の置換あるいは非置換のアルキル基、炭素原子数6から20のアリール基、炭素原子数7から20のアラルキル基、または、−OSiR’3(R’は、それぞれ独立に炭素原子数1から20の炭化水素基である)で示されるトリオルガノシロキシ基である。また、Xは、それぞれ独立にヒドロキシ基または加水分解性基である。更に、aは1から3の整数である)で表される。
−R3−O− (4)
(R3は、炭素原子数1から14の直鎖状もしくは分岐アルキレン基である)で示される繰り返し単位を有する重合体であり、重合体の全ての繰り返し単位中に一般式(4)で表される繰り返し単位が50重量%以上存在することが好ましい。一般式(4)におけるR3は、炭素原子数1から14の、更には2から4の、直鎖状もしくは分岐アルキレン基が好ましい。一般式(4)で示される繰り返し単位の具体例としては、
−CH2O−、−CH2CH2O−、−CH2CH(CH3)O−、−CH2CH(C2H5)O−、−CH2C(CH3)2O−、−CH2CH2CH2CH2O−
等が挙げられる。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。特にシーリング材等に使用される場合には、プロピレンオキシド重合体を主成分とする重合体から成るものが非晶質であることや比較的低粘度である点から好ましい。
−CH2−C(R4)(COOR5)− (5)
(R4は水素原子またはメチル基、R5は炭素原子数1から8のアルキル基を示す)で表される炭素原子数1から8のアルキル基を有する(メタ)アクリル酸エステル単量体単位と、下記一般式(6):
−CH2−C(R4)(COOR6)− (6)
(R4は前記に同じ、R6は炭素原子数9以上のアルキル基を示す)で表される炭素原子数9以上のアルキル基を有する(メタ)アクリル酸エステル単量体単位からなる共重合体に、反応性ケイ素基を有するポリオキシアルキレン系重合体をブレンドして製造する方法である。
−NR7−C(=O)− (7)
(R7は有機基または水素原子を表す)で表される基である。R7の有機基として好ましくは、炭素原子数1から20の置換あるいは非置換の1価の炭化水素基であり、より好ましくは炭素原子数1から8の置換あるいは非置換の1価の炭化水素基である)で表される基である。この構造は極性が比較的高いため、硬化物の強度や基材への接着性が高くなる傾向にあり望ましい。
W−R8−SiR2 3−aXa (8)
(R2、X、aは前記と同じ。R8は2価の有機基であり、より好ましくは炭素原子数1から20の炭化水素基である。Wはヒドロキシ基、カルボキシ基、メルカプト基およびアミノ基(1級または2級)から選ばれた活性水素含有基である)で表されるケイ素化合物のW基を反応させる方法により製造されるものを挙げることができる。この製造方法に関連した、有機重合体の公知の製造法を例示すると、特公昭46−12154号(米国特許3632557号)、特開昭58−109529号(米国特許4374237号)、特開昭62−13430号(米国特許4645816号)、特開平8−53528号(EP0676403)、特開平10−204144号(EP0831108)、特表2003−508561(米国特許6197912号)、特開平6−211879号(米国特許5364955号)、特開平10−53637号(米国特許5756751号)、特開平11−100427号、特開2000−169544号、特開2000−169545号、特開2002−212415号、特許第3313360号、米国特許4067844号、米国特許3711445号、特開2001−323040号等が挙げられる。
O=C=N−R8−SiR2 3−aXa (9)
(R8、R2、X、aは前記に同じ)で示される反応性ケイ素基含有イソシアネート化合物とを反応させることにより製造されるものを挙げることができる。この製造方法に関連した、有機重合体の公知の製造法を例示すると、特開平11−279249号(米国特許5990257号)、特開2000−119365号(米国特許6046270号)、特開昭58−29818号(米国特許4345053号)、特開平3−47825号(米国特許5068304号)、特開平11−60724号、特開2002−155145号、特開2002−249538号、WO03/018658、WO03/059981等が挙げられる。
アミノシラン以外の接着性付与剤の具体例としては、γ−グリシドキシプロピルトリメトキシシラン、γ−グリシドキシプロピルトリエトキシシラン、γ−グリシドキシプロピルメチルジメトキシシラン、β−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、β−(3,4−エポキシシクロヘキシル)エチルトリエトキシシラン等のエポキシ基含有シラン類;γ−イソシアネートプロピルトリメトキシシラン、γ−イソシアネートプロピルトリエトキシシラン、γ−イソシアネートプロピルメチルジエトキシシラン、γ−イソシアネートプロピルメチルジメトキシシラン、(イソシアネートメチル)トリメトキシシラン、(イソシアネートメチル)ジメトキシメチルシラン等のイソシアネート基含有シラン類;γ−メルカプトプロピルトリメトキシシラン、γ−メルカプトプロピルトリエトキシシラン、γ−メルカプトプロピルメチルジメトキシシラン、γ−メルカプトプロピルメチルジエトキシシラン、メルカプトメチルトリエトキシシラン等のメルカプト基含有シラン類;β−カルボキシエチルトリエトキシシラン、β−カルボキシエチルフェニルビス(2−メトキシエトキシ)シラン、N−β−(カルボキシメチル)アミノエチル−γ−アミノプロピルトリメトキシシラン等のカルボキシシラン類;ビニルトリメトキシシラン、ビニルトリエトキシシラン、γ−メタクリロイルオキシプロピルメチルジメトキシシラン、γ−アクリロイルオキシプロピルメチルトリエトキシシラン等のビニル型不飽和基含有シラン類;γ−クロロプロピルトリメトキシシラン等のハロゲン含有シラン類;トリス(トリメトキシシリル)イソシアヌレート等のイソシアヌレートシラン類等を挙げることができる。また、上記シラン類を部分的に縮合した縮合体も使用できる。さらに、これらを変性した誘導体である、アミノ変性シリルポリマー、シリル化アミノポリマー、不飽和アミノシラン錯体、フェニルアミノ長鎖アルキルシラン、アミノシリル化シリコーン、シリル化ポリエステル等も接着性付与剤として用いることができる。
鱗片状または粒状の物質としては、ケイ砂、マイカ等の天然物、合成ゴム、合成樹脂、アルミナ等の無機物が使用される。目地部に充填した際の意匠性を高めるために、外壁の材質、模様等に合わせて、適当な色に着色される。
送液システム:東ソー製HLC−8120GPC
カラム:東ソー製TSK−GEL Hタイプ
溶媒:THF
分子量:ポリスチレン換算
測定温度:40℃
(平均導入数)=[重合体(Q)のヨウ素価−前駆重合体(P)のヨウ素価]/[前駆重合体(P)の水酸基価]。
フラスコに、イソブタノールを添加し105℃に加熱し、窒素置換を行った後、攪拌しながら、窒素雰囲気下で、表1に示すアクリル酸エステル系単量体と重合開始剤とイソブタノールの溶液を5時間かけて滴下し、その後1時間後重合を行った。得られたイソブタノール溶液のポリアクリル系重合体を加熱減圧下でイソブタノールを除去することにより、透明で粘稠な液体を得た。以上により、表1に示す分子量(送液システムとして東ソー(株)製HLC−8120GPCを用い、カラムは東ソー(株)製TSK−GEL Hタイプを用い、溶媒はTHFを用いて測定したポリスチレン換算分子量)と粘度(東京計器(株)製RE80形粘度計を用い、測定温度23.0℃、3°×R14ローターで測定)の反応性ケイ素基を有する(メタ)アクリル酸エステル系重合体を得た。
MMA:メタクリル酸メチル
BA:アクリル酸ブチル
TSMA:メタクリル酸3−(トリメトキシシリル)プロピル
DSMA:メタクリル酸3−(メチルジメトキシシリル)プロピル
2EHA:アクリル酸2−エチルヘキシル
IBA:イソブチルアルコール
V−59:2,2’−アゾビス(2−メチルブチロニトリル)(和光純薬工業(株)製)
V−601:ジメチル−2,2’−アゾビス(2−メチルプロピオネート)(和光純薬工業(株)製)
パーヘキシルO:t−ヘキシルパーオキシ−2−エチルヘキサノエート(日油(株)製)
パーブチルO:t−ブチルパーオキシ−2−エチルヘキサノエート(日油(株)製)
数平均分子量が約2,000のポリオキシプロピレングリコールを開始剤とし、亜鉛ヘキサシアノコバルテートグライム錯体触媒にてプロピレンオキサイドの重合を行い、両末端に水酸基を有する数平均分子量27,900(末端基換算分子量17700)、分子量分布Mw/Mn=1.21のポリオキシプロピレン(P−1)を得た。続いてこの水酸基末端ポリオキシプロピレン(P−1)の水酸基に対して1.2モル当量のナトリウムメトキシドを28%メタノール溶液として添加した。真空脱揮によりメタノールを留去した後、重合体(P−1)の水酸基に対して、さらに1.5モル当量の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た。得られた未精製のアリル基末端ポリオキシプロピレン100重量部に対し、n−ヘキサン300重量部と、水300重量部を混合攪拌した後、遠心分離により水を除去し、得られたヘキサン溶液に更に水300重量部を混合攪拌し、再度遠心分離により水を除去した後、ヘキサンを減圧脱揮により除去した。以上により、末端部位にアリル基を有するポリオキシプロピレン重合体(Q−1)を得た。この重合体(Q−1)500gに対して白金ジビニルジシロキサン錯体溶液150μlを加え、撹拌しながら、ジメトキシメチルシラン4.8gをゆっくりと滴下した。その混合溶液を6%酸素条件下、100℃で6時間反応させた後、未反応のジメトキシメチルシランを減圧下留去する事により、末端にジメトキシメチルシリル基を有する数平均分子量約28,500のポリオキシプロピレン(B−1)を得た。重合体(B−1)はジメトキシメチルシリル基を1つの末端に平均0.8個、1分子中に平均1.6個有することが分かった。
合成例7で得られたジメトキシメチルシリル基を有するポリオキシプロピレン(B−1)と表1に示す溶剤を留去させた反応性ケイ素基を有する(メタ)アクリル酸エステル系重合体を重量比で1:1の比で混合攪拌した後、ガラス瓶へ移し、窒素置換を行い密閉した。30℃もしくは、50℃のオーブンで一晩放置した後、液の状態を観察し、分離した場合を×、分離しなかった場合を○とした。
数平均分子量が約2,000のポリオキシプロピレングリコールを開始剤とし、亜鉛ヘキサシアノコバルテートグライム錯体触媒にてプロピレンオキサイドの重合を行い、両末端に水酸基を有する数平均分子量20,900(末端基換算分子量13,600)、分子量分布Mw/Mn=1.23のポリオキシプロピレン(P−2)を得た。続いてこの水酸基末端ポリオキシプロピレン(P−2)の水酸基に対して1.2モル当量のナトリウムメトキシドを28%メタノール溶液として添加した。真空脱揮によりメタノールを留去した後、重合体(P−2)の水酸基に対して、さらに1.5モル当量の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た。得られた未精製のアリル基末端ポリオキシプロピレン100重量部に対し、n−ヘキサン300重量部と、水300重量部を混合攪拌した後、遠心分離により水を除去し、得られたヘキサン溶液に更に水300重量部を混合攪拌し、再度遠心分離により水を除去した後、ヘキサンを減圧脱揮により除去した。以上により、末端部位にアリル基を有するポリオキシプロピレン重合体(Q−2)を得た。この重合体(Q−2)500gに対して白金ジビニルジシロキサン錯体溶液150μlを加え、撹拌しながら、ジメトキシメチルシラン5.8gをゆっくりと滴下した。その混合溶液を6%酸素条件下、100℃で6時間反応させた後、未反応のジメトキシメチルシランを減圧下留去する事により、末端にジメトキシメチルシリル基を有する数平均分子量約21,100のポリオキシプロピレン(B−2)を得た。重合体(B−2)はジメトキシメチルシリル基を1つの末端に平均0.7個、1分子中に平均1.5個有することが分かった。
合成例7で得られた水酸基末端ポリオキシアルキレン(P−1)の水酸基に対して1.0モル当量のナトリウムメトキシドを28%メタノール溶液として添加した。真空脱揮によりメタノールを留去した後、重合体(P−1)の水酸基に対して、1.0モル当量のアリルグリシジルエーテルを添加して130℃で2時間反応を行った。その後、0.28モル当量のナトリウムメトキシドのメタノール溶液を添加してメタノールを除去し、さらに1.79モル当量の3−クロロ−1−プロペンを添加して末端の水酸基をアリル基に変換した。得られた未精製のアリル基末端ポリオキシプロピレン100重量部に対し、n−ヘキサン300重量部と、水300重量部を混合攪拌した後、遠心分離により水を除去した後、得られたヘキサン溶液に更に水300重量部を混合攪拌し、再度遠心分離により水を除去した後、ヘキサンを減圧脱揮により除去した。以上により、炭素−炭素不飽和結合を2個以上有する末端構造を有するポリオキシプロピレン(Q−3)を得た。重合体(Q−3)は1つの末端部位に炭素−炭素不飽和結合が平均2.0個導入されていることがわかった。
合成例8で得られた水酸基末端ポリオキシアルキレン(P−2)の水酸基に対して1.0モル当量のナトリウムメトキシドを28%メタノール溶液として添加した。重合体(P−2)の水酸基に対して、0.3モル当量のアリルグリシジルエーテルを添加して130℃で2時間反応を行った。その後、0.28モル当量のナトリウムメトキシドのメタノール溶液を添加してメタノールを除去し、さらに1.79モル当量の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、未反応の塩化アリルを減圧脱揮により除去した。得られた未精製のアリル基末端ポリオキシプロピレン100重量部に対し、n−ヘキサン300重量部と、水300重量部を混合攪拌した後、遠心分離により水を除去した後、得られたヘキサン溶液に更に水300重量部を混合攪拌し、再度遠心分離により水を除去した後、ヘキサンを減圧脱揮により除去した。以上により、炭素−炭素不飽和結合を末端に有するポリオキシプロピレン(Q−3)を得た。重合体(Q−3)は1つの末端部位に炭素−炭素不飽和結合が平均1.29個導入されていることがわかった。
表2に示すポリマー成分を合計100重量部、フタル酸エステル系可塑剤(フタル酸ジイソデシル、ジェイ・プラス(株)製、商品名:DIDP)60重量部、表面処理膠質炭酸カルシウム(白石工業(株)製、商品名:白艶華CCR)150重量部、重質炭酸カルシウム(丸尾カルシウム(株)商品名;ナノックス25A)20重量部、酸化チタン(石原産業(株)製、商品名:タイペークR−820)10重量部、カーボンブラック(旭カーボン(株)製、商品名:旭#70)0.2重量部、チクソ性付与剤(楠本化成(株)製、商品名:ディスパロン6500)2重量部、紫外線吸収剤(チバ・スペシャルティ・ケミカルズ(株)製、商品名:チヌビン326)1重量部、光安定剤(チバ・スペシャルティ・ケミカルズ(株)製、商品名:チヌビン770)1重量部を計量、混合して充分混練りした後、小型3本ペイントロールに3回通した。この後、120℃で2時間減圧脱水を実施、50℃以下に冷却後、脱水剤としてビニルトリメトキシシラン(モメンティブ・パフォーマンス・マテリアルズ社製、商品名:Silquest A−171)3重量部、接着性付与剤としてγ−(2−アミノエチル)アミノプロピルトリメトキシシラン(モメンティブ・パフォーマンス・マテリアルズ社製、商品名:Silquest A−1120)2重量部、硬化触媒としてジオクチル錫ジラウレート(日東化成工業(株)製、商品名:ネオスタンU−100)2重量部を加えて混練し、硬化性組成物を得た。この硬化性組成物の、粘度、耐候性、ダンベル引張物性を下記の方法に従って測定した。
100ml用のカップに泡が入らないように充填した。BS型粘度計(東京計器(株)製)とローターNo.7を用いて、23℃50%RH条件下で各組成物の2rpm、10rpmでの粘度を測定した。
上記硬化性組成物を厚さ3mmのシート状試験体にして23℃、50%RH条件に3日間、さらに50℃乾燥機に4日間入れることで完全に硬化させた。3号ダンベル型に打ち抜いた後、島津(株)製オートグラフを用いて引張速度200mm/分で引張試験を行い、100%モジュラス、破断時の伸び(それぞれ、M100、EBと示す)を測定した。
厚さ100μmのシート状試験体の一部を3.5cm角に切り取ったものをメタルウェザー耐候性試験機(ダイプラ・ウィンテス(株)製、メタルウェザーKU−R5C1−A)を用いて、照度を75mW/cm2、ブラックパネル温度を63℃、水を2時間毎に2分間噴霧する設定にて570時間暴露した後取り出し、硬化物表面を観察した。表面クラックなどの異常が観察されたものを×、異常が観察されなかったものを○とした。
窒素気流下でアクリル酸ブチル100重量部、臭化第一銅0.8重量部、アセトニトリル8.8重量部、2,5−ジブロモアジピン酸ジエチル1.8重量部を仕込み、80℃で攪拌した。これにペンタメチルジエチレントリアミン0.18重量部を加えて反応を開始した。途中、アクリル酸ブチル80.0重量部を断続的に追加し、さらにペンタメチルジエチレントリアミンを適宜追加しながら反応溶液の温度が80℃〜90℃となるように加熱攪拌を続けた。アクリル酸ブチルの反応率が95%に達した後、反応容器内を減圧にし、揮発分を除去した。
表3に示すポリマー成分を合計100重量部、PPG3000(分子量3000のジオール型ポリプロピレングリコール)20重量部、表面処理膠質炭酸カルシウム(白石工業(株)製、商品名:白艶華CCR)50重量部、重質炭酸カルシウム(白石工業(株)商品名;ホワイトンSB)50重量部、チクソ性付与剤(楠本化成(株)製、商品名:ディスパロン6500)2重量部を計量、混合して充分混練りした後、小型3本ペイントロールに3回通した。この後、120℃で2時間減圧脱水を実施、50℃以下に冷却後、脱水剤としてビニルトリメトキシシラン(モメンティブ・パフォーマンス・マテリアルズ社製、商品名:Silquest A−171)2重量部、接着性付与剤としてγ−(2−アミノエチル)アミノプロピルトリメトキシシラン(モメンティブ・パフォーマンス・マテリアルズ社製、商品名:Silquest A−1120)3重量部、硬化触媒としてジブチル錫ビスアセチルアセトナート(日東化成工業(株)製、商品名:ネオスタンU−220H)1重量部を加えて混練し、硬化性組成物を得た。この硬化性組成物の粘度、ミニダンベル引張物性、耐熱性を下記の方法に従って測定した。
上記硬化性組成物を厚さ3mmのシート状試験体にして23℃、50%RH条件に3日間、さらに50℃乾燥機に4日間入れることで完全に硬化させた。ミニダンベル型に打ち抜いた後、島津(株)製オートグラフを用いて引張速度200mm/分で引張試験を行い、M100、EBを測定した。
上記ミニダンベルを120℃乾燥機に1週間いれて加熱養生した後、島津(株)製オートグラフを用いて引張速度200mm/分で引張試験を行い、EBを測定した。加熱養生前のEBに対する加熱養生後のEBの変化率を求めた。変化率が100%に近いほど、加熱養生による変化が小さく、耐熱性に優れているといえる。
Claims (14)
- 架橋性シリル基を含有する(メタ)アクリル酸エステルと(メタ)アクリル酸アルキルエステルに由来する繰り返し単位を有する加水分解性ケイ素基含有(メタ)アクリル酸エステル系重合体(A)と、分子鎖末端もしくは分子鎖末端部位のみに架橋性シリル基を有する有機重合体(B)を含有する硬化性組成物であって、(メタ)アクリル酸エステル系重合体(A)が非ニトリル系アゾ系重合開始剤に由来する基を有する硬化性組成物。
- (メタ)アクリル酸エステル系重合体(A)が60℃〜140℃で共重合することで得られる請求項1に記載の硬化性組成物。
- (メタ)アクリル酸エステル系重合体(A)の重合法が溶液重合法である請求項1または2に記載の硬化性組成物。
- 有機重合体(B)の主鎖がポリオキシアルキレン系重合体、(メタ)アクリル酸エステル系重合体、および飽和炭化水素系重合体からなる群から選択される1種以上である請求項1〜3のいずれかに記載の硬化性組成物。
- (メタ)アクリル酸エステル系重合体(A)の重量平均分子量が7000〜14000である請求項1〜4のいずれかに記載の硬化性組成物。
- (メタ)アクリル酸エステル系重合体(A)が一般式(1):
−SiX3 (1)
(式中、Xはヒドロキシ基または加水分解性基であり、3個のXは同一であっても良く、異なっていてもよい)および/または一般式(2):
−SiR1X2 (2)
(R1は、炭素原子数1から20の置換あるいは非置換のアルキル基、炭素原子数6から20のアリール基、炭素原子数7から20のアラルキル基、または、−OSiR’3(R’は、それぞれ独立に炭素原子数1から20の炭化水素基である)で示されるトリオルガノシロキシ基である。また、Xは前記と同じであり、2個のXは同一であっても良く、異なっていてもよい。)で表されるケイ素含有官能基を1分子中に平均して0.5〜2.5個有し、一般式(1)に示すケイ素含有官能基が1分子中に平均して0〜2.0個、一般式(2)に示すケイ素含有官能基が1分子中に平均して0〜2.0個である請求項1〜5のいずれかに記載の硬化性組成物。 - (メタ)アクリル酸エステル系重合体(A)が、エステルを構成するアルコール成分が炭素数1〜4の直鎖状、分岐状または脂環式アルキル基のメタクリル酸エステル0〜15重量部、エステルを構成するアルコール成分が炭素数1〜4の直鎖状、分岐状または脂環式アルキル基のアクリル酸エステル55〜90重量部、エステルを構成するアルコール成分が炭素数8以上の直鎖状、分岐状または脂環式アルキル基の(メタ)アクリル酸エステル5〜30重量部に由来する繰り返し単位を有する請求項1〜6のいずれかに記載の硬化性組成物。
- (メタ)アクリル酸エステル系重合体(A)が、メチルメタクリレート0〜15重量部、ブチルアクリレート55〜90重量部、および2−エチルヘキシルアクリレート5〜30重量部に由来する繰り返し単位を有する請求項1〜7のいずれかに記載の硬化性組成物。
- 架橋性シリル基を含有する(メタ)アクリル酸エステルと(メタ)アクリル酸アルキルエステルに由来する繰り返し単位を有する加水分解性ケイ素基含有(メタ)アクリル酸エステル系重合体(A)と、分子鎖末端もしくは分子鎖末端部位のみに架橋性シリル基を有する有機重合体(B)を含有する硬化性組成物であって、(メタ)アクリル酸エステル系重合体(A)が有機過酸化物系重合開始剤に由来する基を有し、エステルを構成するアルコール成分が炭素数1〜4の直鎖状、分岐状または脂環式アルキル基のメタクリル酸エステル0〜15重量部、エステルを構成するアルコール成分が炭素数1〜4の直鎖状、分岐状または脂環式アルキル基のアクリル酸エステル55〜90重量部、エステルを構成するアルコール成分が炭素数8以上の直鎖状、分岐状または脂環式アルキル基の(メタ)アクリル酸エステル5〜30重量部に由来する繰り返し単位を有し、重量平均分子量が7000〜14000であり、(メタ)アクリル酸エステル系重合体(A)が一般式(1)および/または一般式(2)で表されるケイ素含有官能基を1分子中に平均して0.5〜2.3個有する硬化性組成物。
−SiX3 (1)
(式中、Xはヒドロキシ基または加水分解性基であり、3個のXは同一であっても良く、異なっていてもよい)
−SiR1X2 (2)
(R1は、炭素原子数1から20の置換あるいは非置換のアルキル基、炭素原子数6から20のアリール基、炭素原子数7から20のアラルキル基、または、−OSiR’3(R’は、それぞれ独立に炭素原子数1から20の炭化水素基である)で示されるトリオルガノシロキシ基である。また、Xは前記と同じであり、2個のXは同一であっても良く、異なっていてもよい。) - 有機重合体(B)の主鎖がポリオキシアルキレン系重合体、(メタ)アクリル酸エステル系重合体、および飽和炭化水素系重合体からなる群から選択される1種以上である請求項9に記載の硬化性組成物。
- (メタ)アクリル酸エステル系重合体(A)が、一般式(1)に示すケイ素含有官能基を1分子中に平均して0〜2.0個、一般式(2)に示すケイ素含有官能基を1分子中に平均して0〜2.0個有する請求項9または10に記載の硬化性組成物。
- (メタ)アクリル酸エステル系重合体(A)が、メチルメタクリレート0〜15重量部、ブチルアクリレート55〜90重量部、および2−エチルヘキシルアクリレート5〜30重量部に由来する繰り返し単位を有する請求項9〜11のいずれかに記載の硬化性組成物。
- (メタ)アクリル酸エステル系重合体(A)の23℃、3°×R14の条件で測定されるE型粘度が15〜200Pa・sである請求項1〜12のいずれかに記載の硬化性組成物。
- 有機重合体(B)に含有される架橋性シリル基が重合体1分子中に平均して0.5個以上、数平均分子量がGPCにおけるポリスチレン換算において800から50,000、有機重合体(B)の架橋性シリル基は、一般式(3):
−SiR2 3−aXa (3)
(R2は、それぞれ独立に炭素原子数1から20の置換あるいは非置換のアルキル基、炭素原子数6から20のアリール基、炭素原子数7から20のアラルキル基、または、−OSiR’3(R’は、それぞれ独立に炭素原子数1から20の炭化水素基である)で示されるトリオルガノシロキシ基である。また、Xは、それぞれ独立にヒドロキシ基または加水分解性基である。更に、aは1から3の整数である)で表される請求項1〜13のいずれかに記載の硬化性組成物。
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