JP4754455B2 - Curable composition - Google Patents
Curable composition Download PDFInfo
- Publication number
- JP4754455B2 JP4754455B2 JP2006277558A JP2006277558A JP4754455B2 JP 4754455 B2 JP4754455 B2 JP 4754455B2 JP 2006277558 A JP2006277558 A JP 2006277558A JP 2006277558 A JP2006277558 A JP 2006277558A JP 4754455 B2 JP4754455 B2 JP 4754455B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- polymer
- component
- curable composition
- group
- 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
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- 239000000203 mixture Substances 0.000 title claims description 85
- -1 amine compound Chemical class 0.000 claims description 129
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 64
- 229920000642 polymer Polymers 0.000 claims description 48
- 229920000058 polyacrylate Polymers 0.000 claims description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 31
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 30
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 17
- 229920000620 organic polymer Polymers 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 238000003860 storage Methods 0.000 description 34
- 239000000178 monomer Substances 0.000 description 26
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 17
- 239000003566 sealing material Substances 0.000 description 17
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 15
- 239000003822 epoxy resin Substances 0.000 description 14
- 229920000647 polyepoxide Polymers 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 12
- 230000000704 physical effect Effects 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 229920001451 polypropylene glycol Polymers 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 125000005375 organosiloxane group Chemical group 0.000 description 10
- 239000004014 plasticizer Substances 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 7
- 239000011324 bead Substances 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 150000003141 primary amines Chemical class 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 229910000019 calcium carbonate Inorganic materials 0.000 description 6
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 239000006096 absorbing agent Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 238000011109 contamination Methods 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000013008 thixotropic agent Substances 0.000 description 5
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 4
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 230000003078 antioxidant effect Effects 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
- 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 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000007872 degassing Methods 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 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 4
- 150000004658 ketimines Chemical class 0.000 description 4
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 4
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N Bisphenol F Natural products C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 230000003373 anti-fouling effect Effects 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000012024 dehydrating agents Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 239000007870 radical polymerization initiator Substances 0.000 description 3
- 239000000565 sealant Substances 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
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- PJAKWOZHTFWTNF-UHFFFAOYSA-N (2-nonylphenyl) prop-2-enoate Chemical class CCCCCCCCCC1=CC=CC=C1OC(=O)C=C PJAKWOZHTFWTNF-UHFFFAOYSA-N 0.000 description 2
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-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
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-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
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-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
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
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- 239000004408 titanium dioxide Substances 0.000 description 1
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- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
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- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- OCJLSVQJNZKGKL-UHFFFAOYSA-N tricosane-1,23-diamine Chemical compound NCCCCCCCCCCCCCCCCCCCCCCCN OCJLSVQJNZKGKL-UHFFFAOYSA-N 0.000 description 1
- BPSKTAWBYDTMAN-UHFFFAOYSA-N tridecane-1,13-diamine Chemical compound NCCCCCCCCCCCCCN BPSKTAWBYDTMAN-UHFFFAOYSA-N 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
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- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
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- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
本発明は、硬化性組成物に関し、さらに詳しくは、耐候性及び意匠性に優れた硬化性組成物に関する。 The present invention relates to a curable composition, and more particularly to a curable composition excellent in weather resistance and design properties.
常温硬化性組成物は、シーリング材や接着剤等に用いられているが、過度に艶が出た状態は、安物感を感じさせるなど、意匠性に問題が生じて不都合であるため、これまで種々の艶消し処理が検討されてきた。 Room temperature curable compositions are used for sealing materials, adhesives, etc., but excessively glossy state is inconvenient due to problems in design, such as making it feel cheap. Various matting treatments have been investigated.
従来の艶消し処理として、粒径の比較的大きい充填剤や多孔物質の添加等が行われてきたが、充填剤や多孔物質の添加は、引っ張り物性が低下する等、シーリング材としての物性に問題が生じる場合があった。 Addition of fillers and porous materials with a relatively large particle size has been performed as a conventional matting treatment, but the addition of fillers and porous materials reduces the physical properties of the sealing material, such as reduced tensile properties. A problem sometimes occurred.
上記問題の対応策として、例えば、特許文献1には、艶消し化されたシーリング材として、架橋可能な加水分解性シリル基を末端に有するプロピレンオキシドの重合体並びに、融点が10〜200℃のアミン化合物、融点が10〜200℃のアミド化合物、融点が10〜200℃の脂肪酸、融点が10〜200℃のアルコール及び融点が10〜200℃の脂肪酸エステルからなる群より選ばれる1種以上の化合物からなる室温硬化性組成物が開示されている。しかしながら、上記のような室温硬化性組成物は、艶消し効果は問題ないが、耐候性が充分に得られにくかった。また、特許文献2には、架橋性有機重合体、光硬化性化合物並びに水と反応して第1級及び/又は第2級アミンを生成する化合物からなる高耐候性艶消しシーリング材組成物が開示されているが、該シーリング材組成物には、光硬化性組成物が必要であり、また、耐候性も十分に得られなかった。また、耐候性を向上させる方法として、アクリル系重合体を添加する方法が知られている(例えば、特許文献3参照)。
本発明者らは、十分な艶消し効果を有し、耐候性も優れた硬化性組成物を得るために、種々の検討を重ねてきた。例えば、特許文献1に開示されたような艶消し化されたシーリング材に、耐候性を向上させるためにアクリル系重合体を添加する方法を試みたが、該方法では、製造直後の硬化性組成物には艶消し効果がみられるが、長時間貯蔵することにより艶消し効果が大幅に減少され、貯蔵後の防汚性や耐水接着性、硬化特性等の性能にも悪影響を与えることが判明した。 The present inventors have made various studies in order to obtain a curable composition having a sufficient matting effect and excellent weather resistance. For example, an attempt was made to add an acrylic polymer to a matte sealing material as disclosed in Patent Document 1 in order to improve the weather resistance, but in this method, a curable composition immediately after production was used. Matting effect is seen in objects, but it is found that the matting effect is greatly reduced by storing for a long time, and the performance such as antifouling property, water resistant adhesive property, curing property after storage is also adversely affected did.
通常、シーリング材等の硬化性組成物は、製造後から使用されるまでの間、長時間保管されることが多く、使用者が該硬化性組成物を用いる際にも製造直後の性能が維持される必要があり、貯蔵後に艶消し効果や硬化特性等の性能が大きく低減することは特に問題となる。 Usually, a curable composition such as a sealing material is often stored for a long time until it is used after production, and the performance immediately after production is maintained even when the user uses the curable composition. It is particularly a problem that the performances such as matting effect and curing properties are greatly reduced after storage.
本発明は、シーリング材、接着剤及びコーティング材としての物性を損なうことなく、貯蔵安定性に優れ、貯蔵後も十分な艶消し効果及び防汚性を有し、耐候性の向上した硬化性組成物を提供することを目的とする。 The present invention is a curable composition that has excellent storage stability without sacrificing physical properties as a sealing material, an adhesive and a coating material, has a sufficient matting effect and antifouling property even after storage, and has improved weather resistance The purpose is to provide goods.
上記課題を解決するために、本発明の硬化性組成物の第1の態様は、(A)架橋性シリル基含有有機重合体、(B)アクリル系重合体、(C)水と反応してアミン化合物を生成する化合物、及び(D)硬化触媒を含有し、前記成分(B)が、水酸基非含有アクリル系重合体及び/又は0.05個以上1.0個以下の架橋性シリル基を含有するアクリル系重合体であることを特徴とする。 In order to solve the above-mentioned problems, the first aspect of the curable composition of the present invention reacts with (A) a crosslinkable silyl group-containing organic polymer, (B) an acrylic polymer, and (C) water. A compound that forms an amine compound, and (D) a curing catalyst , wherein the component (B) contains a hydroxyl group-free acrylic polymer and / or 0.05 or more and 1.0 or less crosslinkable silyl group. It is an acrylic polymer to contain .
本発明の硬化性組成物の第1の態様において、上記成分(A)として、架橋性シリル基含有ポリオキシアルキレン系重合体、架橋性シリル基含有アクリル変性ポリオキシアルキレン系重合体、及び/又は架橋性シリル基含有メタクリル変性ポリオキシアルキレン系重合体を用いることが好適である。 In the first embodiment of the curable composition of the present invention, as the component (A), a crosslinkable silyl group-containing polyoxyalkylene polymer, a crosslinkable silyl group-containing acrylic modified polyoxyalkylene polymer, and / or It is preferable to use a crosslinkable silyl group-containing methacryl-modified polyoxyalkylene polymer.
本発明の硬化性組成物の第1の態様において、上記成分(A)として、(A1)架橋性シリル基含有アクリル系重合体を用いることにより、耐候性をより向上させることができ好ましい。 In the 1st aspect of the curable composition of this invention, a weather resistance can be improved more by using (A1) crosslinkable silyl group containing acrylic polymer as said component (A), and it is preferable.
本発明の硬化性組成物の第1の態様において、上記成分(B)として、水酸基非含有アクリル系重合体、0.05個以上1.0個以下の架橋性シリル基を含有するアクリル系重合体、又は(メタ)アクリル酸エステル−フルオロオレフィン共重合体を用いることが好適である。 In the first embodiment of the curable composition of the present invention, as the component (B), an acrylic polymer containing a hydroxyl group-free acrylic polymer and 0.05 to 1.0 crosslinkable silyl groups. It is preferable to use a polymer or a (meth) acrylic acid ester-fluoroolefin copolymer.
本硬化性組成物の第2の態様は、(A1)架橋性シリル基含有アクリル系重合体、(C)水と反応してアミン化合物を生成する化合物、及び(D)硬化触媒を含有することを特徴とする。 The second aspect of the present curable composition contains (A1) a crosslinkable silyl group-containing acrylic polymer, (C) a compound that reacts with water to form an amine compound, and (D) a curing catalyst. It is characterized by.
本発明の硬化性組成物の第1の態様において、(E1)一分子中に少なくとも一個のアルコキシシリル基を有するアミン化合物を含有することが好ましい。 In the first aspect of the curable composition of the present invention, it is preferable that (E1) an amine compound having at least one alkoxysilyl group in one molecule.
本発明の硬化性組成物の第1の態様において、上記アミン化合物が、第1級及び/又は第2級アミンであることが好ましい。また、上記アミン化合物が脂肪族アミンであると、より貯蔵前後共に艶消し効果が増し好適である。 In the first embodiment of the curable composition of the present invention, the amine compound is preferably a primary and / or secondary amine. Further, it is preferable that the amine compound is an aliphatic amine because the matting effect is increased both before and after storage.
上記硬化性組成物の第1〜第2の態様に、(E)水と反応して一分子中に少なくとも一個のアルコキシシリル基を有するアミン化合物を生成する化合物をさらに添加すると貯蔵後の硬化特性の低下を防止することができ、且つ貯蔵後の耐水接着性を改善させることができ好適である。 When the compound which reacts with water and produces | generates the amine compound which has an at least 1 alkoxysilyl group in one molecule is further added to the 1st- 2nd aspect of the said curable composition, the hardening characteristic after storage It is possible to prevent the decrease in water resistance and improve the water-resistant adhesiveness after storage.
また、上記硬化性組成物の第1〜第2の態様に、(E1)一分子中に少なくとも一個のアルコキシシリル基を有するアミン化合物及び(E2)カルボニル化合物をさらに添加すると貯蔵後の硬化特性の低下を防止することができ、且つ貯蔵後の耐水接着性を改善させることができ好適である。 In addition, when (E1) an amine compound having at least one alkoxysilyl group in one molecule and (E2) a carbonyl compound are further added to the first to second embodiments of the curable composition, the curing characteristics after storage can be improved. It is preferable because it can prevent the deterioration and can improve the water-resistant adhesion after storage.
さらに、上記硬化性組成物の第1〜第2の態様に、(F)エポキシ樹脂をさらに添加することが、耐水性を向上させることができ好ましい。 Furthermore, it is preferable that the (F) epoxy resin is further added to the first and second embodiments of the curable composition because the water resistance can be improved.
本発明によれば、作業性や耐久性などのシーリング材、接着剤及びコーティング材として必要な物性を損なうことなく、貯蔵安定性に優れ、貯蔵後も十分な艶消し効果及び防汚性を有し、耐候性の向上した硬化性組成物を提供することができる。 According to the present invention, it has excellent storage stability without sacrificing physical properties required for sealing materials, adhesives, and coating materials such as workability and durability, and has a sufficient matting effect and antifouling property after storage. In addition, a curable composition having improved weather resistance can be provided.
以下に本発明の実施の形態を説明するが、これらの実施の形態は例示的に示されるもので、本発明の技術思想から逸脱しない限り種々の変形が可能なことはいうまでもない。 Embodiments of the present invention will be described below, but these embodiments are exemplarily shown, and it goes without saying that various modifications can be made without departing from the technical idea of the present invention.
本発明の硬化性組成物の第1の態様は、下記成分(A)、(B)、(C)及び(D)を含有する硬化性組成物である。
(A)架橋性シリル基含有有機重合体、
(B)アクリル系重合体、
(C)水と反応してアミン化合物を生成する化合物、及び
(D)硬化触媒
The 1st aspect of the curable composition of this invention is a curable composition containing the following component (A), (B), (C) and (D).
(A) a crosslinkable silyl group-containing organic polymer,
(B) an acrylic polymer,
(C) a compound that reacts with water to produce an amine compound, and (D) a curing catalyst.
本発明においては、(A)成分として用いられる架橋性シリル基含有有機重合体としては、従来公知のものを広く使用でき、分子内に、シロキサン結合を形成することによって架橋してゴム状硬化物を形成する、シリル基を1個以上含有する有機重合体であれば、特に限定されない。このような架橋性シリル基含有有機重合体(A)としては、例えば、特許文献4〜16中に開示されているものを挙げることができる。上記架橋性シリル基含有有機重合体(A)としては具体的には、分子内に1個以上の架橋性シリル基を含有する、主鎖がそれぞれオルガノシロキサンを含有していてもよい、ポリオキシアルキレン系重合体、ビニル変性ポリオキシアルキレン系重合体、ビニル系重合体、ポリエステル重合体、アクリル酸エステル重合体、メタアクリル酸エステル重合体、これらの共重合体や混合物等を挙げることができる。架橋性シリル基は、シーリング材の硬化性や硬化後の物性等の点から、分子内に1〜5個含まれるのが好ましい。更に、架橋性シリル基は、架橋しやすく製造しやすい下記一般式(1)で示されるものが好ましい。 In the present invention, as the crosslinkable silyl group-containing organic polymer used as the component (A), conventionally known ones can be widely used. A rubber-like cured product is crosslinked by forming a siloxane bond in the molecule. There is no particular limitation as long as it is an organic polymer containing one or more silyl groups. Examples of the crosslinkable silyl group-containing organic polymer (A) include those disclosed in Patent Documents 4 to 16. Specifically, as the crosslinkable silyl group-containing organic polymer (A), a polyoxy group containing one or more crosslinkable silyl groups in the molecule and the main chain may each contain an organosiloxane. Examples thereof include an alkylene polymer, a vinyl-modified polyoxyalkylene polymer, a vinyl polymer, a polyester polymer, an acrylate polymer, a methacrylic acid ester polymer, a copolymer and a mixture thereof. It is preferable that 1-5 crosslinkable silyl groups are contained in a molecule | numerator from points, such as the sclerosis | hardenability of a sealing material, and the physical property after hardening. Further, the crosslinkable silyl group is preferably one represented by the following general formula (1) which is easy to crosslink and easy to produce.
(式中、R1は炭化水素基であり、炭素数1〜20のアルキル基、炭素数6〜20のアリール基又は炭素数7〜20のアラルキル基が好ましく、メチル基が最も好ましい。Xで示される反応性基はハロゲン原子、水素原子、水酸基、アルコキシ基、アシルオキシ基、ケトキシメート基、アミド基、酸アミド基、メルカプト基、アルケニルオキシ基及びアミノオキシ基より選ばれる基であり、Xが複数の場合には、Xは同じ基であっても異なった基であってもよい。このうちXはアルコキシ基が好ましく、メトキシ基が最も好ましい。aは0、1又は2の整数であり、1が最も好ましい。) Wherein R 1 is a hydrocarbon group, preferably an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms, and most preferably a methyl group. The reactive group shown is a group selected from a halogen atom, a hydrogen atom, a hydroxyl group, an alkoxy group, an acyloxy group, a ketoximate group, an amide group, an acid amide group, a mercapto group, an alkenyloxy group and an aminooxy group. In this case, X may be the same group or different groups, among which X is preferably an alkoxy group, most preferably a methoxy group, a is an integer of 0, 1 or 2, Is most preferred.)
架橋性シリル基含有有機重合体(A)の主鎖は、硬化後の引張接着性、モジュラス等の物性の点から、オルガノシロキサンを含有していてもよい、ポリオキシアルキレン系重合体及び/又はビニル変性ポリオキシアルキレン系重合体が好ましい。特に、成分(A)として、分子内に1個以上の架橋性シリル基を含有する、主鎖がそれぞれオルガノシロキサンを含有していてもよい、ポリオキシアルキレン系重合体、アクリル変性ポリオキシアルキレン系重合体、及び/又はメタクリル変性ポリオキシアルキレン系重合体、並びにこれらの混合物が好ましく、主鎖がそれぞれオルガノシロキサンを含有していてもよい、ポリオキシプロピレン系重合体、アクリル変性ポリオキシプロピレン系重合体、及び/又はメタクリル変性ポリオキシプロピレン系重合体であるものが更に好ましい。 The main chain of the crosslinkable silyl group-containing organic polymer (A) has a polyoxyalkylene polymer and / or may contain an organosiloxane from the viewpoint of physical properties such as tensile adhesiveness after curing and modulus. A vinyl-modified polyoxyalkylene polymer is preferred. In particular, as component (A), one or more crosslinkable silyl groups in the molecule, the main chain may each contain an organosiloxane, a polyoxyalkylene polymer, an acrylic-modified polyoxyalkylene system Polymers and / or methacryl-modified polyoxyalkylene polymers, and mixtures thereof are preferred, and the main chain may contain an organosiloxane, and the polyoxypropylene polymer, acrylic-modified polyoxypropylene polymer More preferably, the polymer is a polymer and / or a methacryl-modified polyoxypropylene polymer.
前記の分子内に1個以上の架橋性シリル基を含有する、オルガノシロキサンを含有していてもよいビニル変性ポリオキシアルキレン系重合体は、分子内に1個以上の架橋性シリル基を含有する、オルガノシロキサンを含有していてもよいポリオキシアルキレン系重合体の存在下で、ラジカル重合開始剤の添加あるいは紫外線照射などの通常のラジカル重合方法により、1種又は2種以上のビニル系単量体を重合させる等して得ることができる(特許文献17及び特許文献18等が参考として挙げられるが、これらに限定されるものではない)。 The vinyl-modified polyoxyalkylene polymer which may contain an organosiloxane and contains one or more crosslinkable silyl groups in the molecule contains one or more crosslinkable silyl groups in the molecule. In the presence of a polyoxyalkylene polymer that may contain an organosiloxane, one or more vinyl monomers are added by a conventional radical polymerization method such as addition of a radical polymerization initiator or ultraviolet irradiation. It can be obtained by polymerizing the body (Patent Document 17 and Patent Document 18 are cited as reference, but are not limited thereto).
ビニル系単量体としては、分子内に1個以上の重合性不飽和結合を有する化合物であって、例えば、エチレン、プロピレン、イソブチレン、ブタジエン、クロロプレン、塩化ビニル、塩化ビニリデン、アクリル酸、メタクリル酸、酢酸ビニル、アクリロニトリル、スチレン、クロルスチレン、2−メチルスチレン、ジビニルベンゼン、アクリル酸メチル、アクリル酸エチル、アクリル酸イソブチル、アクリル酸2−エチルヘキシル、アクリル酸2−ヒドロキシエチル、アクリル酸ベンジル、グリシジルアクリレート、メタクリル酸メチル、メタクリル酸エチル、メタクリル酸イソブチル、メタクリル酸2−エチルヘキシル、メタクリル酸2−ヒドロキシエチル、メタクリル酸ベンジル、グリシジルメタクリレート、アクリルアミド、メタクリルアミド、n−メチロールアクリルアミド、エトキシ化フェノールアクリレート、エトキシ化パラクミルフェノールアクリレート、エトキシ化ノニルフェノールアクリレート、プロポキシ化ノニルフェノールアクリレート、2−エチルヘキシルカルビトールアクリレート、N−ビニル−2−ピロリドン、イソボルニルアクリレート、エトキシ化ビスフェノールFジアクリレート、エトキシ化ビスフェノールAジアクリレート、エトキシ化イソシアヌル酸ジアクリレート、トリプロピレングリコールジアクリレート、ペンタエリスリトールジアクリレートモノステアレート、ポリエチレングリコールジアクリレート、ポリプロピレングリコールジアクリレート、ペンタエリスリトールトリアクリレート、トリメチロールプロパントリアクリレート、エトキシ化イソシアヌル酸トリアクリレート、プロポキシ化トリメチロールプロパントリアクリレート、エトキシ化トリメチロールプロパントリアクリレート、ジペンタエリスリトールペンタアクリレート、ジペンタエリスリトールヘキサアクリレート、ジトリメチロールプロパンテトラアクリレート、ペンタエリスリトールテトラアクリレート、ポリウレタンジアクリレート、ω−カルボキシ−ポリカプロラクトンモノアクリレート、フタル酸モノヒドロキシエチルアクリレート、アクリル酸ダイマー、2−ヒドロキシ−3−フェノキシプロピルアクリレート、ポリエステルポリアクリレート、1,6−ヘキサンジオールジアクリレート、2−(2−エトキシエトキシ)エチルアクリレート、ステアリルアクリレート、テトラヒドロフルフリルアクリレート、ラウリルアクリレート、2−フェノキシアクリレート、イソデシルアクリレート、イソオクチルアクリレート、トリデシルアクリレート、カプロラクトンアクリレート、ジンクジアクリレート、1,3−ブタンジオールジアクリレート、1,4−ブタンジオールジアクリレート、ジエチレングリコールジアクリレート、トリエチレングリコールジアクリレート、テトラエチレングリコールジアクリレート、プロポキシ化ネオペンチルグリコールジアクリレート、プロポキシ化グリセリントリアクリレート、エトキシ化ペンタエリスリトールテトラアクリレート、ペンタアクリレートエステル、テトラヒドロフルフリルメタクリレート、シクロヘキシルメタクリレート、イソデシルメタクリレート、ラウリルメタクリレート、ポリプロピレングリコールジメタクリレート、トリエチレングリコールジメタクリレート、エチレングリコールジメタクリレート、テトラエチレングリコールジメタクリレート、ポリエチレングリコールジメタクリレート、1,4−ブタンジオールジメタクリレート、ジエチレングリコールジメタクリレート、1,6−ヘキサンジオールジメタクリレート、ネオペンチルグリコールジメタクリレート、1,3−ブタンジオールジメタクリレート、エトキシ化ビスフェノールAジメタクリレート、ジンクジメタクリレート、トリメチロールプロパントリメタクリレート、また、次の化学式(2)〜(25)で示される各化合物などが挙げられるが、これらに限定されるものではない。 The vinyl monomer is a compound having one or more polymerizable unsaturated bonds in the molecule, for example, ethylene, propylene, isobutylene, butadiene, chloroprene, vinyl chloride, vinylidene chloride, acrylic acid, methacrylic acid. , Vinyl acetate, acrylonitrile, styrene, chlorostyrene, 2-methylstyrene, divinylbenzene, methyl acrylate, ethyl acrylate, isobutyl acrylate, 2-ethylhexyl acrylate, 2-hydroxyethyl acrylate, benzyl acrylate, glycidyl acrylate , Methyl methacrylate, ethyl methacrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate, 2-hydroxyethyl methacrylate, benzyl methacrylate, glycidyl methacrylate, acrylamide, methacrylate Amides, n-methylol acrylamide, ethoxylated phenol acrylate, ethoxylated paracumyl phenol acrylate, ethoxylated nonyl phenol acrylate, propoxylated nonyl phenol acrylate, 2-ethylhexyl carbitol acrylate, N-vinyl-2-pyrrolidone, isobornyl acrylate, ethoxy Bisphenol F diacrylate, ethoxylated bisphenol A diacrylate, ethoxylated isocyanuric acid diacrylate, tripropylene glycol diacrylate, pentaerythritol diacrylate monostearate, polyethylene glycol diacrylate, polypropylene glycol diacrylate, pentaerythritol triacrylate, tri Methylolpropane triacre relay , Ethoxylated isocyanuric acid triacrylate, propoxylated trimethylolpropane triacrylate, ethoxylated trimethylolpropane triacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, ditrimethylolpropane tetraacrylate, pentaerythritol tetraacrylate, polyurethane diacrylate , Ω-carboxy-polycaprolactone monoacrylate, monohydroxyethyl acrylate phthalate, acrylic acid dimer, 2-hydroxy-3-phenoxypropyl acrylate, polyester polyacrylate, 1,6-hexanediol diacrylate, 2- (2-ethoxy Ethoxy) ethyl acrylate, stearyl acrylate, tetrahydrofur Ryl acrylate, lauryl acrylate, 2-phenoxy acrylate, isodecyl acrylate, isooctyl acrylate, tridecyl acrylate, caprolactone acrylate, zinc diacrylate, 1,3-butanediol diacrylate, 1,4-butanediol diacrylate, diethylene glycol di Acrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, propoxylated neopentyl glycol diacrylate, propoxylated glycerin triacrylate, ethoxylated pentaerythritol tetraacrylate, pentaacrylate ester, tetrahydrofurfuryl methacrylate, cyclohexyl methacrylate, isodecyl methacrylate , Lauryl metaclay , Polypropylene glycol dimethacrylate, triethylene glycol dimethacrylate, ethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, 1,4-butanediol dimethacrylate, diethylene glycol dimethacrylate, 1,6-hexanediol dimethacrylate, Neopentyl glycol dimethacrylate, 1,3-butanediol dimethacrylate, ethoxylated bisphenol A dimethacrylate, zinc dimethacrylate, trimethylolpropane trimethacrylate, and other compounds represented by the following chemical formulas (2) to (25) However, it is not limited to these.
ビニル系単量体は、オルガノシロキサンを含有していてもよいポリオキシアルキレン系重合体100重量部に対して、0.1〜1000重量部、更には1〜200重量部の範囲で使用するのが好ましい。なお、分子内に1個以上の架橋性シリル基を含有する、オルガノシロキサンを含有していてもよいビニル変性ポリオキシアルキレン系重合体としては、分子内に1個以上の架橋性シリル基を含有する、オルガノシロキサンを含有していてもよいポリオキシアルキレン系重合体と、前記ビニル系単量体の1種以上を重合して得られる重合体に架橋性シリル基を導入して得られる、架橋性シリル基含有ビニル系重合体とをブレンドしたものを使用することもできる。 The vinyl monomer is used in the range of 0.1 to 1000 parts by weight, more preferably 1 to 200 parts by weight, based on 100 parts by weight of the polyoxyalkylene polymer that may contain organosiloxane. Is preferred. The vinyl-modified polyoxyalkylene polymer containing one or more crosslinkable silyl groups in the molecule and optionally containing an organosiloxane contains one or more crosslinkable silyl groups in the molecule. A crosslinkable polymer obtained by introducing a crosslinkable silyl group into a polyoxyalkylene polymer that may contain an organosiloxane and a polymer obtained by polymerizing at least one of the vinyl monomers. A blend of a functional silyl group-containing vinyl polymer can also be used.
また、成分(A)として(A1)架橋性シリル基含有アクリル系重合体を用いることにより、耐候性が向上し、好適である。(A1)架橋性シリル基含有アクリル系重合体としては、従来公知のものを広く使用でき、特に限定されないが、例えば、特許文献14及び19〜26中に開示されているものを挙げることができる。具体的には、分子内に1個以上の架橋性シリル基を有し、それぞれオルガノシロキサンを含有していてもよい、主鎖が本質的に(メタ)アクリル酸、(メタ)アクリル酸エステル、(メタ)アクリロニトリル、(メタ)アクリルアミド等のアクリル系単量体の1種以上を(共)重合して得られる重合体である化合物やそれらの混合物を主成分とする組成物が挙げられる。上記アクリル系単量体としては、特に限定されないが、(メタ)アクリル酸エステルが好ましい。 Moreover, weather resistance improves by using (A1) crosslinkable silyl group containing acrylic polymer as a component (A), and it is suitable. As the (A1) crosslinkable silyl group-containing acrylic polymer, conventionally known ones can be widely used, and are not particularly limited, but examples thereof include those disclosed in Patent Documents 14 and 19 to 26. . Specifically, the main chain is essentially (meth) acrylic acid, (meth) acrylic acid ester, which has one or more crosslinkable silyl groups in the molecule and may contain organosiloxane. Examples thereof include a composition comprising as a main component a compound that is a polymer obtained by (co) polymerizing one or more acrylic monomers such as (meth) acrylonitrile and (meth) acrylamide, and a mixture thereof. Although it does not specifically limit as said acrylic monomer, (meth) acrylic acid ester is preferable.
上記アクリル酸エステルとしては、例えば、(メタ)アクリル酸メチル、(メタ)アクリル酸エチル、(メタ)アクリル酸−n−プロピル、(メタ)アクリル酸イソプロピル、(メタ)アクリル酸−n−ブチル、(メタ)アクリル酸イソブチル、(メタ)アクリル酸s−ブチル、(メタ)アクリル酸t−ブチル、(メタ)アクリル酸−n−ペンチル、(メタ)アクリル酸ネオペンチル、(メタ)アクリル酸−n−ヘキシル、(メタ)アクリル酸−n−ヘプチル、(メタ)アクリル酸−n−オクチル、(メタ)アクリル酸2−エチルヘキシル、(メタ)アクリル酸ノニル、(メタ)アクリル酸デシル、(メタ)アクリル酸イソデシル、(メタ)アクリル酸ドデシル、(メタ)アクリル酸ラウリル、(メタ)アクリル酸トリデシルおよび(メタ)アクリル酸ステアリル等の(メタ)アクリル酸アルキル;(メタ)アクリル酸シクロヘキシル、(メタ)アクリル酸イソボルニルおよび(メタ)アクリル酸トリシクロデシニル等のアクリル酸脂環式アルキル;(メタ)アクリル酸フェニル、(メタ)アクリル酸トルイル及び(メタ)アクリル酸ベンジル等の芳香族アクリル酸エステル類、(メタ)アクリル酸ヒドロキシエチル、(メタ)アクリル酸ヒドロキシブチル、(メタ)アクリル酸ヒドロキシプロピルおよび(メタ)アクリル酸ヒドロキシエチルのε−カプロラクトン付加反応物等の(メタ)アクリル酸ヒドロキシアルキル;(メタ)アクリル酸2−メトキシエチル、(メタ)アクリル酸3−メトキシブチル、(メタ)アクリル酸2−アミノエチル、(メタ)アクリル酸ジメチルアミノエチル、(メタ)アクリル酸クロロエチル、(メタ)アクリル酸トリフルオロエチル、(メタ)アクリル酸トリフルオロメチルメチル、および(メタ)アクリル酸テトラヒドロフルフリル等のヘテロ原子含有アクリル酸エステル類が挙げられるが、これらに限らない。また、これらの中の1種類または2種類以上を併用してもよい。上記(メタ)アクリル酸エステルの中でも、ガラス転移温度が低い重合体が得られるという理由から、アクリル酸ブチル、アクリル酸2−エチルヘキシルおよびアクリル酸2−メトキシエチルが好ましい。 Examples of the acrylate ester include methyl (meth) acrylate, ethyl (meth) acrylate, (meth) acrylate-n-propyl, isopropyl (meth) acrylate, (meth) acrylate-n-butyl, (Meth) acrylic acid isobutyl, (meth) acrylic acid s-butyl, (meth) acrylic acid t-butyl, (meth) acrylic acid-n-pentyl, (meth) acrylic acid neopentyl, (meth) acrylic acid-n- Hexyl, (meth) acrylic acid-n-heptyl, (meth) acrylic acid-n-octyl, (meth) acrylic acid 2-ethylhexyl, (meth) acrylic acid nonyl, (meth) acrylic acid decyl, (meth) acrylic acid Isodecyl, dodecyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate and (meth) Alkyl (meth) acrylates such as stearyl acrylate; alicyclic alkyl acrylates such as cyclohexyl (meth) acrylate, isobornyl (meth) acrylate and tricyclodecynyl (meth) acrylate; phenyl (meth) acrylate , Aromatic acrylic esters such as toluyl (meth) acrylate and benzyl (meth) acrylate, hydroxyethyl (meth) acrylate, hydroxybutyl (meth) acrylate, hydroxypropyl (meth) acrylate and (meth) Hydroxyalkyl (meth) acrylate such as ε-caprolactone addition reaction product of hydroxyethyl acrylate; 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, 2-aminoethyl (meth) acrylate , Dimethylamino (meth) acrylate Examples include heteroatom-containing acrylic esters such as ethyl, chloroethyl (meth) acrylate, trifluoroethyl (meth) acrylate, trifluoromethyl methyl (meth) acrylate, and tetrahydrofurfuryl (meth) acrylate. Not limited to these. Moreover, you may use together 1 type, or 2 or more types of these. Among the above (meth) acrylic acid esters, butyl acrylate, 2-ethylhexyl acrylate and 2-methoxyethyl acrylate are preferred because a polymer having a low glass transition temperature is obtained.
なお、成分(A1)として、上記アクリル系単量体以外にこれと共重合可能な単量体を共重合させることも可能である。共重合可能な単量体としては、特に限定されないが、例えば、フルオロオレフィン類、α−オレフィン類、ビニルエステル類およびビニルエーテル類などのビニル系単量体が挙げられる。また、成分(A1)として、上記架橋性シリル基含有アクリル系重合体と他の重合体、例えば、上記したような架橋性シリル基含有ポリオキシアルキレン重合体や架橋性シリル基含有ビニル変性ポリオキシアルキレン重合体等、との混合物を用いることも可能であり、本発明に含まれる。架橋性シリル基含有アクリル系重合体と他の重合体との混合物を用いる場合、混合物中の架橋性シリル基含有アクリル系重合体の配合割合が30質量%以上であることが好ましい。 As the component (A1), in addition to the acrylic monomer, a monomer copolymerizable therewith can be copolymerized. The copolymerizable monomer is not particularly limited, and examples thereof include vinyl monomers such as fluoroolefins, α-olefins, vinyl esters and vinyl ethers. Further, as the component (A1), the crosslinkable silyl group-containing acrylic polymer and other polymers such as the above-mentioned crosslinkable silyl group-containing polyoxyalkylene polymer and crosslinkable silyl group-containing vinyl-modified polyoxy It is also possible to use a mixture with an alkylene polymer or the like, which is included in the present invention. When using the mixture of a crosslinkable silyl group containing acrylic polymer and another polymer, it is preferable that the mixture ratio of the crosslinkable silyl group containing acrylic polymer in a mixture is 30 mass% or more.
本発明において、上記架橋性シリル基含有有機重合体(A)の数平均分子量は1000以上、特に6000〜30000で分子量分布の狭いものが、硬化前の粘度が低いので取り扱い易く、硬化後の強度、伸び、モジュラス等の物性が好適である。上記成分(A)は1種のみで用いても良く、2種以上併用してもよい。 In the present invention, the crosslinkable silyl group-containing organic polymer (A) has a number average molecular weight of 1000 or more, particularly 6,000 to 30,000, and a narrow molecular weight distribution, which is easy to handle because of its low viscosity before curing, and strength after curing. Physical properties such as elongation and modulus are preferred. The said component (A) may be used only by 1 type, and may be used together 2 or more types.
本発明において、上記(B)アクリル系重合体を含有させることにより、耐候性が向上する。上記成分(B)は、可塑剤として使用することもできる。成分(B)として用いられるアクリル系重合体としては、(メタ)アクリル酸、(メタ)アクリル酸エステル、(メタ)アクリロニトリル、(メタ)アクリルアミド等のアクリル系単量体から選ばれる1種以上を重合させたアクリル系(共)重合体が使用でき、好ましい例として、(メタ)アクリル酸エステル単量体を主成分としたものであり、エステル部分の炭素数が1〜20のアクリル酸エステルが挙げられる。例えば、成分(A1)において上述したような(メタ)アクリル酸エステル単量体が挙げられるがこれらに限定されない。 In this invention, a weather resistance improves by containing the said (B) acrylic polymer. The said component (B) can also be used as a plasticizer. The acrylic polymer used as the component (B) includes at least one selected from acrylic monomers such as (meth) acrylic acid, (meth) acrylic acid ester, (meth) acrylonitrile, (meth) acrylamide, and the like. A polymerized acrylic (co) polymer can be used. As a preferable example, a (meth) acrylic acid ester monomer is a main component, and an acrylic acid ester having 1 to 20 carbon atoms in the ester moiety is used. Can be mentioned. Examples include (meth) acrylic acid ester monomers as described above in component (A1), but are not limited thereto.
アクリル系重合体(B)は、架橋性シリル基を含有していなくても架橋性シリル基を含有していてもよく、特に限定されないが、架橋性シリル基を含有しているものは、1分子中に平均して0.05個以上2.0個以下が好ましく、0.1個以上1.0個以下が特に好ましい。架橋性シリル基を有するアクリル系重合体としては、特に限定されないが、例えば、特許文献30及び特許文献31中に開示されているものが挙げられる。 The acrylic polymer (B) may not contain a crosslinkable silyl group or may contain a crosslinkable silyl group, and is not particularly limited. The average number in the molecule is preferably 0.05 or more and 2.0 or less, and particularly preferably 0.1 or more and 1.0 or less. Although it does not specifically limit as an acryl-type polymer which has a crosslinkable silyl group, For example, what is indicated in patent document 30 and patent document 31 is mentioned.
また、アクリル系重合体(B)には、上記アクリル系単量体以外にこれと共重合可能な単量体を共重合させることも可能である。共重合可能な単量体としては、例えば、フルオロオレフィン類、α−オレフィン類、ビニルエステル類およびビニルエーテル類などのビニル系単量体が挙げられる。特に、(メタ)アクリル酸エステル単量体とフルオロオレフィン単量体を主構成単量体とする(メタ)アクリル酸エステル−フルオロオレフィン共重合体が好適に用いられる。(メタ)アクリル酸エステル−フルオロオレフィン共重合体としては、従来公知のものを広く使用でき、例えば、特許文献25〜29中に開示されているものを挙げることができる。フルオロオレフィン単量体としては、例えば、テトラフルオロエチレン、クロロトリフルオロエチレン、ヘキサフルオロプロピレン、ジクロロジフルオロエチレン、トリフルオロエチレン、フッ化ビニリデン、フッ化ビニルおよびパーフルオロ(アルキルビニルエーテル)等が挙げられ、これらの中でも、重合性の面よりテトラフルオロエチレン、クロロトリフルオロエチレン、ヘキサフルオロプロピレン及びトリフルオロエチレンが好ましく、更に好ましくはテトラフルオロエチレン、クロロトリフルオロエチレン及びトリフルオロエチレンである。 Further, the acrylic polymer (B) can be copolymerized with a monomer copolymerizable therewith in addition to the acrylic monomer. Examples of the copolymerizable monomer include vinyl monomers such as fluoroolefins, α-olefins, vinyl esters and vinyl ethers. In particular, a (meth) acrylic acid ester-fluoroolefin copolymer having a (meth) acrylic acid ester monomer and a fluoroolefin monomer as main constituent monomers is preferably used. As the (meth) acrylic ester-fluoroolefin copolymer, conventionally known ones can be widely used, and examples thereof include those disclosed in Patent Documents 25 to 29. Examples of the fluoroolefin monomer include tetrafluoroethylene, chlorotrifluoroethylene, hexafluoropropylene, dichlorodifluoroethylene, trifluoroethylene, vinylidene fluoride, vinyl fluoride and perfluoro (alkyl vinyl ether). Among these, tetrafluoroethylene, chlorotrifluoroethylene, hexafluoropropylene and trifluoroethylene are preferable from the viewpoint of polymerizability, and tetrafluoroethylene, chlorotrifluoroethylene and trifluoroethylene are more preferable.
上記アクリル系重合体(B)は、水性媒体中での懸濁重合や乳化重合、有機溶剤中での溶液重合、或いは塊状重合など通常の方法で製造することができる。有機溶剤としては、通常用いられるものが使用でき、例えば、テトラヒドロフランおよびジオキサン等の環状エーテル類;ベンゼン、トルエンおよびキシレン等の芳香族炭化水素化合物;酢酸エチルおよび酢酸ブチル等のエステル類;アセトン、メチルエチルケトンおよびシクロヘキサノン等のケトン類;メタノール、エタノールおよびイソプロパノール等のアルコール類等が挙げられ、これらの1種または2種以上を用いることができる。 The acrylic polymer (B) can be produced by a usual method such as suspension polymerization or emulsion polymerization in an aqueous medium, solution polymerization in an organic solvent, or bulk polymerization. As the organic solvent, those usually used can be used, for example, cyclic ethers such as tetrahydrofuran and dioxane; aromatic hydrocarbon compounds such as benzene, toluene and xylene; esters such as ethyl acetate and butyl acetate; acetone and methyl ethyl ketone And ketones such as cyclohexanone; alcohols such as methanol, ethanol and isopropanol, and the like, and one or more of these can be used.
上記重合に用いるラジカル発生型重合開始剤としては、ジイソプロピルパーオキシジカーボネート、ターシャリーブチルパーオキシピバレート、ベンゾイルパーオキサイド、ラウロイルパーオキサイドおよびジターシャリーブチルパーオキサイド等の過酸化物、またはアゾビスイソブチロニトリル、アゾビスイソバレロニトリル等のアゾ化合物、過硫酸アンモニウム、過硫酸カリウム等の無機過酸化物が使用できる。また、連鎖移動剤は耐候性の低下につながるため、使用しないことが好ましい。 Examples of radical generating polymerization initiators used in the polymerization include peroxides such as diisopropyl peroxydicarbonate, tertiary butyl peroxypivalate, benzoyl peroxide, lauroyl peroxide and ditertiary butyl peroxide, or azobisiso An azo compound such as butyronitrile and azobisisovaleronitrile, and an inorganic peroxide such as ammonium persulfate and potassium persulfate can be used. Moreover, it is preferable not to use a chain transfer agent because it leads to a decrease in weather resistance.
上記重合は、重合温度が20℃〜350℃、好ましくは150℃〜350℃、圧力が常圧〜10MPaで行い、加圧の場合は耐圧オートクレーブを用い、5分〜20時間の反応時間で行うことができる。重合方法はバッチ重合、セミバッチ重合、或いは連続重合でもよい。 The above polymerization is carried out at a polymerization temperature of 20 ° C. to 350 ° C., preferably 150 ° C. to 350 ° C. and a pressure of atmospheric pressure to 10 MPa. be able to. The polymerization method may be batch polymerization, semi-batch polymerization, or continuous polymerization.
上記アクリル系重合体(B)のガラス転移温度は10℃以下が好ましく、より好ましくは0℃以下、さらにより好ましくは−10℃以下である。また、重量平均分子量は500以上20,000以下が好ましく、700以上10,000以下であることがより好ましい。ガラス転移温度が10℃より高いと、低温における作業性が悪くなる。また、重量平均分子量が20,000を越えると、十分な可塑性が発現されないため作業性が悪くなり、一方、500未満であると、低分子の重合体がブリードするため汚染性が低下する。 The glass transition temperature of the acrylic polymer (B) is preferably 10 ° C or lower, more preferably 0 ° C or lower, and even more preferably -10 ° C or lower. The weight average molecular weight is preferably 500 or more and 20,000 or less, and more preferably 700 or more and 10,000 or less. When the glass transition temperature is higher than 10 ° C., workability at low temperatures is deteriorated. On the other hand, when the weight average molecular weight exceeds 20,000, sufficient plasticity is not exhibited and workability is deteriorated. On the other hand, when the weight average molecular weight is less than 500, the low molecular weight polymer bleeds, resulting in a decrease in contamination.
(B)成分の配合割合は、特に限定されるものではないが、(A)成分100重量部に対して、(B)成分を1〜400重量部用いることが好ましく、5〜200重量部用いることがより好ましい。上記アクリル系重合体は、単独で用いても良く、2種以上併用してもよい。 The blending ratio of the component (B) is not particularly limited, but it is preferable to use 1 to 400 parts by weight, preferably 5 to 200 parts by weight of the component (B) with respect to 100 parts by weight of the component (A). It is more preferable. The said acrylic polymer may be used independently and may be used together 2 or more types.
上記(C)成分として用いられる水と反応してアミン化合物を生成する化合物としては、具体的には、原料入手の容易性、貯蔵安定性、水との反応性などの点から、アミン化合物のケチミン化合物、エナミン化合物、及び/又はアルジミン化合物が好適例として挙げられる。 As the compound that reacts with water used as the component (C) to produce an amine compound, specifically, from the viewpoint of availability of raw materials, storage stability, reactivity with water, and the like, Preferred examples include ketimine compounds, enamine compounds, and / or aldimine compounds.
上記ケチミン化合物、エナミン化合物及びアルジミン化合物はそれぞれ、(C1)アミン化合物と(C2)カルボニル化合物との脱水反応により得ることができる。上記成分(C)の製造方法は特に限定されず、公知の方法を用いることができる。 The ketimine compound, enamine compound and aldimine compound can be obtained by dehydration reaction of (C1) amine compound and (C2) carbonyl compound, respectively. The manufacturing method of the said component (C) is not specifically limited, A well-known method can be used.
上記成分(C1)アミン化合物としては、特に限定されないが、例えば、第1級及び/又は第2級アミンが挙げられる。特に、上記成分(C1)アミン化合物が脂肪族アミンであると、より貯蔵前後共に艶消し効果が増し好適である。 Although it does not specifically limit as said component (C1) amine compound, For example, a primary and / or a secondary amine is mentioned. In particular, it is preferable that the component (C1) amine compound is an aliphatic amine because the matting effect is increased both before and after storage.
上記第1級及び/又は第2級アミンとしては、特に限定されないが、例えば、第1級アミンとしては、モノアミンとして、ブチルアミン、ヘキシルアミン、へプチルアミン、2−エチルヘキシルアミン、オクチルアミン、3−メトキシプロピルアミン、テトラデシルアミン、ペンタデシルアミン、セチルアミン、ステアリルアミン、トリメチルシクロヘキシルアミン、ベンジルアミン、アニリン等を挙げることができ、ジアミンとして、エチレンジアミン、1,3−ジアミノプロパン、1,2−ジアミノプロパン、1,4−ジアミノブタン、ヘキサメチレンジアミン、1,7−ジアミノへプタン、トリメチルヘキサメチレンジアミン、1,8−ジアミノオクタン、1,9−ジアミノノナン、1,10−ジアミノデカン、1,11−ジアミノウンデカン、1,12−ジアミノドデカン、1,13−ジアミノトリデカン、1,14−ジアミノテトラデカン、1,15−ジアミノペンタデカン、1,16−ジアミノヘキサデカン、1,17−ジアミノヘプタデカン、1,18−ジアミノオクタデカン、1,19−ジアミノノナデカン、1,20−ジアミノエイコサン、1,21−ジアミノヘンティコサン、1,22−ジアミノドコサン、1,23−ジアミノトリコサン、1,24−ジアミノテトラコサン、イソホロンジアミン、ジアミノジシクロへキシルメタン、3,9−ビス(3−アミノプロピル)−2,4,8,10−テトラオキサスピロ(5,5)ウンデカン、キシレンジアミン、フェニレンジアミン、ジアミノジフェニルメタン、ジアミノジエチルフェニルメタン、ポリオキシエチレンジアミン、ポリオキシプロピレンジアミンなどを挙げることができ、ポリアミンとして、トリ(メチルアミノ)へキサンなどを挙げることができる。第2級アミンとしては、例えば、ジラウリルアミン、ジステアリルアミン、メチルラウリルアミンなどのモノアミン、N,N′−ジラウリルプロピルアミン、N,N′−ジステアリルブチルアミン、N−ブチル−N′−ラウリルエチルアミン、N−ブチル−N′−ラウリルプロピルアミン、N−ラウリル−N′−ステアリルブチルアミン等のジアミンを挙げることができる。第1級、第2級混合アミンとしては、N−ラウリルプロピレンジアミン、N−ステアリルプロピレンジアミンなどを挙げることができる。第1級、第2級混合ポリアミンとしては、ジエチレントリアミン、トリエチレンテトラミン、メチルアミノプロピルアミンなどを挙げることができる。特に、ステアリルアミン、ヘキサメチレンジアミン、N−ステアリルプロピレンジアミン等の脂肪族アミンがより艶消し効果が大きく好ましい。 Although it does not specifically limit as said primary and / or secondary amine, For example, as primary amine, as monoamine, butylamine, hexylamine, heptylamine, 2-ethylhexylamine, octylamine, 3-methoxy Examples thereof include propylamine, tetradecylamine, pentadecylamine, cetylamine, stearylamine, trimethylcyclohexylamine, benzylamine, aniline, etc. Examples of diamines include ethylenediamine, 1,3-diaminopropane, 1,2-diaminopropane, 1,4-diaminobutane, hexamethylenediamine, 1,7-diaminoheptane, trimethylhexamethylenediamine, 1,8-diaminooctane, 1,9-diaminononane, 1,10-diaminodecane, 1,11-diaminou Decane, 1,12-diaminododecane, 1,13-diaminotridecane, 1,14-diaminotetradecane, 1,15-diaminopentadecane, 1,16-diaminohexadecane, 1,17-diaminoheptadecane, 1,18- Diaminooctadecane, 1,19-diaminononadecane, 1,20-diaminoeicosane, 1,2-diaminohenticosane, 1,2-diaminodocosane, 1,23-diaminotricosane, 1,24-diaminotetra Kosan, isophoronediamine, diaminodicyclohexylmethane, 3,9-bis (3-aminopropyl) -2,4,8,10-tetraoxaspiro (5,5) undecane, xylenediamine, phenylenediamine, diaminodiphenylmethane, Diaminodiethylphenylmethane, polyoxye Diamine, etc. can be mentioned polyoxypropylene diamine, polyamine, etc. hexane tri (methylamino) can be exemplified. Examples of secondary amines include monoamines such as dilaurylamine, distearylamine, and methyllaurylamine, N, N'-dilaurylpropylamine, N, N'-distearylbutylamine, and N-butyl-N'-. Examples thereof include diamines such as laurylethylamine, N-butyl-N′-laurylpropylamine, and N-lauryl-N′-stearylbutylamine. Examples of the primary and secondary mixed amines include N-lauryl propylene diamine and N-stearyl propylene diamine. Examples of the primary and secondary mixed polyamines include diethylenetriamine, triethylenetetramine, and methylaminopropylamine. In particular, aliphatic amines such as stearylamine, hexamethylenediamine, and N-stearylpropylenediamine are preferred because they have a greater matting effect.
上記成分(C1)アミン化合物は、シーリング材の硬化表面の艶、光沢を顕著に低く抑えるためには、融点が35℃以上のもの或いは分子内に1個以上の窒素原子と2個以上の窒素原子結合活性水素を含有するものが、艶消し作用が大きく、意匠性に優れており好適である。融点が35℃未満のものは、耐熱性、特に夏期の高温で軟化しやすく、融点が100℃を越えるものはシーリング材表面が固く、脆くなりやすく、シーリング材の基本特性である弾性を損ねやすいので、上記成分(C1)アミン化合物は融点が35℃以上、特に40〜100℃のものが好ましい。 The component (C1) amine compound has a melting point of 35 ° C. or higher, or one or more nitrogen atoms and two or more nitrogen atoms in the molecule in order to suppress the gloss and gloss of the cured surface of the sealing material to a significantly low level. Those containing atomic bond active hydrogen are suitable because they have a large matting effect and are excellent in design. Those with a melting point of less than 35 ° C tend to soften at high temperatures, especially at high temperatures in the summer, and those with a melting point of more than 100 ° C are hard and brittle and tend to impair elasticity, which is a basic characteristic of sealing materials. Therefore, the component (C1) amine compound preferably has a melting point of 35 ° C or higher, particularly 40 to 100 ° C.
上記成分(C2)カルボニル化合物としては公知のものが含まれ、例えば、アセトアルデヒド、プロピオンアルデヒド、n−ブチルアルデヒド、イソブチルアルデヒド、n−アミルアルデヒド、イソヘキシルアルデヒド、ジエチルアセトアルデヒド、グリオキサール、ベンズアルデヒド、フェニルアセトアルデヒド等のアルデヒド類;シクロペンタノン、トリメチルシクロペンタノン、シクロヘキサノン、メチルシクロヘキサノン、トリメチルシクロヘキサノン等の環状ケトン類;アセトン、メチルエチルケトン、メチルプロピルケトン、メチルイソプロピルケトン、メチルイソブチルケトン、メチル−tert−ブチルケトン、ジエチルケトン、ジプロピルケトン、ジイソプロピルケトン、ジブチルケトン、ジイソブチルケトン等の脂肪族ケトン類;アセトフェノン、ベンゾフェノン、プロピオフェノン等の芳香族ケトン;及びアセチルアセトン、アセト酢酸メチル、アセト酢酸エチル、マロン酸ジメチル、マロン酸ジエチル、マロン酸メチルエチル、ジベンゾイルメタン等の下記一般式(26)で示されるβ−ジカルボニル化合物が挙げられるが、これらに限定されるものではない。このうち、メチルイソブチルケトン、ジプロピルケトン、フェニルアセトアルデヒド、及び活性メチレン基を有するβ−ジカルボニル化合物〔下記一般式(26)で示される化合物〕がより好ましい。 Examples of the component (C2) carbonyl compound include known compounds such as acetaldehyde, propionaldehyde, n-butyraldehyde, isobutyraldehyde, n-amylaldehyde, isohexaldehyde, diethylacetaldehyde, glyoxal, benzaldehyde, phenylacetaldehyde, and the like. Aldehydes; cyclic ketones such as cyclopentanone, trimethylcyclopentanone, cyclohexanone, methylcyclohexanone, trimethylcyclohexanone; acetone, methyl ethyl ketone, methyl propyl ketone, methyl isopropyl ketone, methyl isobutyl ketone, methyl tert-butyl ketone, diethyl ketone , Dipropyl ketone, diisopropyl ketone, dibutyl ketone, diisobutyl ketone, etc. And aromatic ketones such as acetophenone, benzophenone and propiophenone; and the following general formula (26) such as acetylacetone, methyl acetoacetate, ethyl acetoacetate, dimethyl malonate, diethyl malonate, methyl ethyl malonate, However, it is not limited to these. Among these, methyl isobutyl ketone, dipropyl ketone, phenylacetaldehyde, and a β-dicarbonyl compound having an active methylene group [compound represented by the following general formula (26)] are more preferable.
〔式中、R2及びR3は同一又は異なって、それぞれ炭素数1〜16個のアルキル基(例えば、メチル、エチル、プロピル、ブチル、ヘプチル、ヘキシル、オクチル、ノニル、デシル、ウンデシル、ヘキサデシル等)、炭素数6〜12個のアリール基(例えば、フェニル、トリル、ヘキシル、ナフチル等)、又は炭素数1〜4個のアルコキシル基(例えば、メトキシ、エトキシ、プロオキシ、プトキシ等)を意味する。〕 [Wherein, R 2 and R 3 are the same or different and each has an alkyl group having 1 to 16 carbon atoms (for example, methyl, ethyl, propyl, butyl, heptyl, hexyl, octyl, nonyl, decyl, undecyl, hexadecyl, etc. ), An aryl group having 6 to 12 carbon atoms (for example, phenyl, tolyl, hexyl, naphthyl, etc.) or an alkoxyl group having 1 to 4 carbon atoms (for example, methoxy, ethoxy, prooxy, putoxy, etc.). ]
上記成分(C)の配合割合は、水と反応して生成するアミン化合物が架橋性シリル基含有有機重合体(A)100重量部に対して0.05〜50重量部、特に0.1〜20重量部となるように配合するのが好ましい。上記水と反応してアミン化合物を生成する化合物は、単独で使用しても良く、2種以上併用しても良い。 The mixing ratio of the component (C) is 0.05 to 50 parts by weight, particularly 0.1 to 100 parts by weight, based on 100 parts by weight of the crosslinkable silyl group-containing organic polymer (A). It is preferable to blend so as to be 20 parts by weight. The compound which reacts with water to produce an amine compound may be used alone or in combination of two or more.
上記成分(D)として用いられる硬化触媒としては、成分(A)に対し硬化触媒の作用を示すものであれば、特に限定されないが、例えば、有機金属化合物やアミン類等が挙げられ、特にシラノール縮合触媒を用いることが好ましい。上記シラノール縮合触媒としては、例えば、スタナスオクトエート、ジブチル錫ジオクトエート、ジブチル錫ジラウレート、ジブチル錫マレエート、ジブチル錫ジアセテート、ジブチル錫ジアセチルアセトナート、ジブチル錫オキサイド、ジブチル錫ビストリエトキシシリケート、ジブチル錫ジステアレート、ジオクチル錫ジラウレート、ジオクチル錫ジバーサテート、オクチル酸錫及びナフテン酸錫等の有機錫化合物;ジブチル錫オキサイドとフタル酸エステルとの反応物等;テトラブチルチタネート、テトラプロピルチタネート等のチタン酸エステル類;アルミニウムトリスアセチルアセトナート、アルミニウムトリスエチルアセトアセテート、ジイソプロポキシアルミニウムエチルアセトアセテート等の有機アルミニウム化合物類;ジルコニウムテトラアセチルアセトナート、チタンテトラアセチルアセトナート等のキレート化合物類;オクチル酸鉛;シラノール縮合触媒として公知のその他の酸性触媒及び塩基性触媒等が挙げられる。このうち高い架橋速度、毒性及び輝発性の比較的低い液体である点から、ジブチル錫ジアセチルアセトナートが特に好ましい。 The curing catalyst used as the component (D) is not particularly limited as long as it exhibits the action of a curing catalyst with respect to the component (A). Examples thereof include organometallic compounds and amines, and particularly silanols. It is preferable to use a condensation catalyst. Examples of the silanol condensation catalyst include stannous octoate, dibutyltin dioctoate, dibutyltin dilaurate, dibutyltin maleate, dibutyltin diacetate, dibutyltin diacetylacetonate, dibutyltin oxide, dibutyltin bistriethoxysilicate, dibutyltin distearate. Organotin compounds such as dioctyltin dilaurate, dioctyltin diversate, tin octylate and tin naphthenate; reactants of dibutyltin oxide and phthalate; titanates such as tetrabutyl titanate and tetrapropyl titanate; aluminum Organoaluminum compounds such as trisacetylacetonate, aluminum trisethylacetoacetate, diisopropoxyaluminum ethylacetoacetate; Co tetra acetylacetonate, chelate compounds such as titanium tetraacetyl acetonate; lead octylate; silanol condensation catalyst as known other acidic catalysts and basic catalysts, and the like. Of these, dibutyltin diacetylacetonate is particularly preferred because it is a liquid having a high crosslinking rate, toxicity and relatively low luminescence.
成分(D)の配合割合は、架橋速度、硬化物の物性などの点から、架橋性シリル基含有有機重合体(A)100重量部に対して、0.1〜30重量部、特に0.5〜20重量部用いることが好ましい。これらの硬化触媒は、単独で使用しても良く、2種以上併用しても良い。 Component (D) is blended in an amount of 0.1 to 30 parts by weight, particularly 0. It is preferable to use 5 to 20 parts by weight. These curing catalysts may be used alone or in combination of two or more.
本発明の硬化性組成物には、貯蔵後の硬化特性の低下を防止し、且つ貯蔵後の耐水接着性を改善するために、更に(E)水と反応して一分子中に少なくとも一個のアルコキシシリル基を有するアミン化合物を生成する化合物を添加することが好適である。なお、本発明において、貯蔵後の硬化速度、硬化物の硬さ及び厚み等の硬化特性の悪化を硬化特性の低下と称す。該(E)水と反応して一分子中に少なくとも一個のアルコキシシリル基を有するアミン化合物を生成する化合物としては、具体的には、原料入手の容易性、貯蔵安定性、水との反応性などの点から、一分子中に少なくとも一個のアルコキシシリル基を有するアミン化合物のケチミン化合物、エナミン化合物、及び/又はアルジミン化合物が好適例として挙げられる。 The curable composition of the present invention further comprises (E) at least one reaction in one molecule by reacting with water in order to prevent deterioration of the curing characteristics after storage and to improve water-resistant adhesion after storage. It is preferable to add a compound that forms an amine compound having an alkoxysilyl group. In the present invention, deterioration of curing characteristics such as curing speed after storage, hardness and thickness of the cured product is referred to as deterioration of curing characteristics. Specific examples of the compound that reacts with water (E) to produce an amine compound having at least one alkoxysilyl group in one molecule include easy availability of raw materials, storage stability, and reactivity with water. In view of the above, preferred examples include ketimine compounds, enamine compounds, and / or aldimine compounds, which are amine compounds having at least one alkoxysilyl group in one molecule.
上記ケチミン化合物、エナミン化合物及びアルジミン化合物はそれぞれ、(E1)一分子中に少なくとも一個のアルコキシシリル基を有するアミン化合物と(E2)カルボニル化合物との脱水反応により得ることができる。上記成分(E)の製造方法は特に限定されず、公知の方法を用いることができる。 Each of the ketimine compound, enamine compound and aldimine compound can be obtained by a dehydration reaction between (E1) an amine compound having at least one alkoxysilyl group in one molecule and (E2) a carbonyl compound. The manufacturing method of the said component (E) is not specifically limited, A well-known method can be used.
上記成分(E1)一分子中に少なくとも一個のアルコキシシリル基を有するアミン化合物と成分(E2)カルボニル化合物による脱水反応生成物について説明すれば、次の通りである。成分(E1)アルコキシシリル基を有するアミン化合物は、特に限定されないが、例えば、下記一般式(27)で示されるものを挙げることができる。 The dehydration product of the amine compound having at least one alkoxysilyl group in one molecule of the component (E1) and the component (E2) carbonyl compound will be described as follows. Component (E1) The amine compound having an alkoxysilyl group is not particularly limited, and examples thereof include those represented by the following general formula (27).
[式(27)中、n=0,1,2、R4及びR5は同一又は異なって、それぞれ炭素数1〜4個の炭化水素基、R6は炭素数1〜10個の炭化水素基、Zは水素原子又は炭素数1〜4個のアミノアルキル基を意味する。] [In the formula (27), n = 0, 1, 2, R 4 and R 5 are the same or different and each is a hydrocarbon group having 1 to 4 carbon atoms, and R 6 is a hydrocarbon having 1 to 10 carbon atoms. The group Z represents a hydrogen atom or an aminoalkyl group having 1 to 4 carbon atoms. ]
ここで、R4及びR5としては、メチル、エチル、プルピル、ブチルといったアルキル基、ビニル、アリル、プロペニル、ブテニルといったアルケニル基などが挙げられ、特にアルキル基が好ましい。R6としてはメチレン、エチレン、プロピレン、ブチレンなどのアルキレン基、フェニレンなどのアリーレン基やアルキレンアリーレン基等が挙げられるが、特にアルキレン基が好ましい。nは好ましくは0又は1である。 Here, examples of R 4 and R 5 include alkyl groups such as methyl, ethyl, propyl, and butyl, and alkenyl groups such as vinyl, allyl, propenyl, and butenyl, with alkyl groups being particularly preferable. Examples of R 6 include alkylene groups such as methylene, ethylene, propylene and butylene, arylene groups such as phenylene, alkylene arylene groups, and the like, and alkylene groups are particularly preferable. n is preferably 0 or 1.
具体例としては、下記式(28)〜(35)で示される化合物や、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、N−(β−アミノエチル)−γ−アミノプロピルメチルジメトキシシラン等に代表されるアミノシラン類等を挙げることができる。これらの中では、γ−アミノプロピルトリメトキシシラン、γ−アミノプロピルメチルジメトキシシラン、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等が好ましい。 Specific examples include compounds represented by the following formulas (28) to (35), N- (β-aminoethyl) -γ-aminopropyltrimethoxysilane, N- (β-aminoethyl) -γ-aminopropyl. Examples include aminosilanes typified by methyldimethoxysilane. Among these, γ-aminopropyltrimethoxysilane, γ-aminopropylmethyldimethoxysilane, N- (β-aminoethyl) -γ-aminopropyltrimethoxysilane and the like are preferable.
成分(E2)カルボニル化合物としては、特に、限定されず、成分(C2)の説明において例示したようなカルボニル化合物が用いられる。 The carbonyl compound is not particularly limited as the component (E2), and carbonyl compounds exemplified in the description of the component (C2) are used.
本発明に用いる(E)水と反応して一分子中に少なくとも一個のアルコキシシリル基を有するアミン化合物を生成する化合物の製造方法は、どのような方法でも良いがモノマー純度が50〜95%で、かつアミノ基封鎖率が90%以上のものを製造するためには以下の方法が望ましい。アルコキシシリル基を有するアミン化合物とカルボニル化合物との反応はカルボニル化合物中に加熱下でアルコキシシリル基を有するアミン化合物を導入し、その導入中に生成した水をカルボニル化合物と共に共沸留去する。この際のアルコキシシリル基を有するアミン化合物に対し、過剰量のカルボニル化合物を反応させることが好ましい。 (E) The method for producing the compound that reacts with water and produces an amine compound having at least one alkoxysilyl group in one molecule may be any method, but the monomer purity is 50 to 95%. In order to produce those having an amino group blocking ratio of 90% or more, the following method is desirable. In the reaction between an amine compound having an alkoxysilyl group and a carbonyl compound, the amine compound having an alkoxysilyl group is introduced into the carbonyl compound under heating, and water generated during the introduction is distilled off azeotropically with the carbonyl compound. In this case, it is preferable to react an excess amount of the carbonyl compound with the amine compound having an alkoxysilyl group.
また、このアルコキシシリル基を有するアミン化合物の導入温度(反応温度)はカルボニル化合物と水との共沸温度付近からカルボニル化合物の還流温度付近までとすることが好ましく、アルコキシシリル基を有するアミン化合物はこの温度範囲で導入することが好ましい。例えば、カルボニル化合物をメチルイソブチルケトンとし、これをアルコキシシリル基を有するアミン化合物と反応させる場合には、メチルイソブチルケトンと水との共沸温度が80℃程度となり、このメチルイソブチルケトンの還流温度が130℃であることから、アルコキシシリル基を有するアミン化合物の導入温度は80〜130℃とすればよい。この反応のためのアルコキシシリル基を有するアミン化合物の導入方法は任意とされるが、これをカルボニル化合物と速やかに反応させるためには、これを液中に導入することが好ましい。この導入時間も任意とされるが、これは30分〜20時間程度とすることが好ましい。また、この反応は湿気があると反応生成物が加水分解してしまうために、反応は窒素、アルゴンなどの不活性ガス下で行うことが好ましく、カルボニル化合物中の水分もできるかぎり少なくすることが好ましい。 The introduction temperature (reaction temperature) of the amine compound having an alkoxysilyl group is preferably from about the azeotropic temperature of the carbonyl compound and water to about the reflux temperature of the carbonyl compound. It is preferable to introduce in this temperature range. For example, when methyl isobutyl ketone is used as the carbonyl compound and this is reacted with an amine compound having an alkoxysilyl group, the azeotropic temperature of methyl isobutyl ketone and water is about 80 ° C., and the reflux temperature of this methyl isobutyl ketone is Since it is 130 degreeC, the introduction temperature of the amine compound which has an alkoxy silyl group should just be 80-130 degreeC. The method for introducing an amine compound having an alkoxysilyl group for this reaction is arbitrary, but it is preferable to introduce it into a liquid in order to react it quickly with a carbonyl compound. This introduction time is also optional, but it is preferably about 30 minutes to 20 hours. In addition, since the reaction product hydrolyzes in the presence of moisture, the reaction is preferably performed under an inert gas such as nitrogen or argon, and the water content in the carbonyl compound should be reduced as much as possible. preferable.
この(E)水と反応して一分子中に少なくとも一個のアルコキシシリル基を有するアミン化合物を生成する化合物の製造は、上記したように、カルボニル化合物に加熱下でアルコキシシリル基を有するアミン化合物を導入して反応させ、この導入中から生成した水をカルボニル化合物と共に共沸留去するものであるが、このアルコキシシリル基を有するアミン化合物の導入終了後も、系内の水分留去のためにはカルボニル化合物との共沸留去とすることが好ましい。 (E) As described above, the production of a compound that reacts with water to produce an amine compound having at least one alkoxysilyl group in one molecule is performed by adding an amine compound having an alkoxysilyl group to a carbonyl compound under heating. Introduced and reacted, water generated during the introduction is azeotropically distilled together with the carbonyl compound. Even after the introduction of the amine compound having an alkoxysilyl group, the water in the system is distilled off. Is preferably azeotropic distillation with a carbonyl compound.
この留出温度はカルボニル化合物の還流温度まで上昇させ、還流温度になってから30分〜2時間程度留出を続けるか、或いはアルコキシシリル基を有するアミン化合物導入終了直後に減圧濃縮による系内から未反応カルボニル化合物を留去することが好ましい。なお、還流温度になってから30分〜2時間程度留去を続けると、系内に水分がなくなるために、これは安定で加水分解縮合の進行は生じにくいが、未反応カルボニル化合物はできるだけ速く系内から留去することが好ましい。このような方法で得た、目的とする水と反応して一分子中に少なくとも一個のアルコキシシリル基を有するアミン化合物を生成する化合物は、アルコキシ基の加水分解縮合で生成するアルコキシシランオリゴマーとの混合物として得られるが、オリゴマー量が従来の製造方法に比較して少なくなり、また残存アミノ基量も少ないものである。このものを高純度で得るためにはこの水と反応して一分子中に少なくとも一個のアルコキシシリル基を有するアミン化合物を生成する化合物を蒸留単離することもできるが、このように蒸留単離したものは、高コストとなり、また接着性も十分でないため、本発明の硬化性組成物に使用するのには望ましくない。 The distillation temperature is raised to the reflux temperature of the carbonyl compound, and the distillation is continued for about 30 minutes to 2 hours after the reflux temperature is reached, or from the system by concentration under reduced pressure immediately after the introduction of the amine compound having an alkoxysilyl group. It is preferable to distill off the unreacted carbonyl compound. If the distillation is continued for about 30 minutes to 2 hours after the reflux temperature is reached, water will disappear in the system, which is stable and hardly undergoes hydrolysis and condensation. However, the unreacted carbonyl compound is as fast as possible. It is preferable to distill from the system. The compound obtained by such a method that reacts with the target water to produce an amine compound having at least one alkoxysilyl group in one molecule is obtained with an alkoxysilane oligomer produced by hydrolysis condensation of an alkoxy group. Although obtained as a mixture, the amount of oligomer is smaller than that of conventional production methods, and the amount of residual amino groups is also small. In order to obtain this product with high purity, it is possible to distill and isolate a compound that reacts with this water to produce an amine compound having at least one alkoxysilyl group in one molecule. This is not desirable for use in the curable composition of the present invention because of the high cost and insufficient adhesion.
本発明においては、上記(E)水と反応して一分子中に少なくとも一個のアルコキシシリル基を有するアミン化合物を生成する化合物として、上記の方法等によって得られる、モノマー純度が50〜95%、好ましくは70〜95%、更に好ましくは80〜95%で、かつアミノ基封鎖率が90%以上、好ましくは95%以上のものを使用する。モノマー純度が50%より低いと、組成物の保存安定性が悪く、95%より高いと組成物の接着性が悪くなり、またアミノ基封鎖率が90%より少ないと、組成物の保存安定性が悪くなるため好ましくない。 In the present invention, as a compound that reacts with water (E) to produce an amine compound having at least one alkoxysilyl group in one molecule, the monomer purity obtained by the above method or the like is 50 to 95%, It is preferably 70 to 95%, more preferably 80 to 95%, and an amino group blocking ratio of 90% or more, preferably 95% or more. When the monomer purity is lower than 50%, the storage stability of the composition is poor. When the monomer purity is higher than 95%, the adhesiveness of the composition is deteriorated. When the amino group blocking ratio is less than 90%, the storage stability of the composition is low. Is not preferable because of worsening.
上記成分(E)の配合割合は、特に限定されないが、成分(A)100重量部に対して、成分(E)0.01〜20重量部程度が好ましく、0.1〜10重量部がさらに好ましい。これらの水と反応して一分子中に少なくとも一個のアルコキシシリル基を有するアミン化合物を生成する化合物は、単独で使用しても良く、2種以上併用しても良い。 The blending ratio of the component (E) is not particularly limited, but is preferably about 0.01 to 20 parts by weight and more preferably 0.1 to 10 parts by weight with respect to 100 parts by weight of the component (A). preferable. These compounds that react with water to produce an amine compound having at least one alkoxysilyl group in one molecule may be used alone or in combination of two or more.
本発明の硬化性組成物には、貯蔵後の硬化特性の低下を防止し、且つ貯蔵後の耐水接着性を改善するために、(E1)一分子中に少なくとも一個のアルコキシシリル基を有するアミン化合物及び(E2)カルボニル化合物をさらに添加することが好適である。成分(E1)及び成分(E2)は、それぞれ成分(E)の説明において挙げた一分子中に少なくとも一個のアルコキシシリル基を有するアミン化合物及びカルボニル化合物を同様に用いることができる。上記成分(E1)及び成分(E2)は、配合物中で脱水反応を生じる。該脱水反応は、必要に応じて加熱処理等の反応処理を行っても良いが、特別な工程を行わずに、時間経過により進行させることが可能である。 The curable composition of the present invention includes (E1) an amine having at least one alkoxysilyl group in one molecule in order to prevent a decrease in curing characteristics after storage and to improve water-resistant adhesion after storage. It is preferred to further add the compound and (E2) carbonyl compound. As the component (E1) and the component (E2), an amine compound and a carbonyl compound each having at least one alkoxysilyl group in one molecule mentioned in the description of the component (E) can be used in the same manner. The component (E1) and the component (E2) cause a dehydration reaction in the blend. The dehydration reaction may be carried out by a reaction treatment such as a heat treatment as necessary, but can be progressed over time without performing a special step.
上記成分(E1)及び(E2)の配合割合は、特に限定されないが、成分(E1)及び(E2)が、成分(A)100重量部に対してそれぞれ0.05〜50重量部、特に0.1〜20重量部となるように配合するのが好ましい。さらに、[成分(E1)のモル量]/[成分(E2)のモル量]が0.1〜5.0の範囲であることが好ましく、0.5〜2.0の範囲であることがさらに好ましい。アミン化合物及びカルボニル化合物は、それぞれ単独で使用しても良く、2種以上併用しても良い。 The blending ratio of the components (E1) and (E2) is not particularly limited, but the components (E1) and (E2) are each 0.05 to 50 parts by weight, particularly 0, with respect to 100 parts by weight of the component (A). It is preferable to mix | blend so that it may become 1-20 weight part. Further, [molar amount of component (E1)] / [molar amount of component (E2)] is preferably in the range of 0.1 to 5.0, and preferably in the range of 0.5 to 2.0. Further preferred. The amine compound and the carbonyl compound may be used alone or in combination of two or more.
本発明の硬化性組成物には、耐水性向上の為に(F)エポキシ樹脂をさらに添加することが好適である。該(F)エポキシ樹脂としては、従来公知のものを広く使用でき、特に限定されないが、ビスフェノール型エポキシ樹脂やポリオキシアルキレン骨格を有するエポキシ樹脂を用いることが好ましい。上記ポリオキシアルキレン骨格を有するエポキシ樹脂としては、ポリアルキレンオキシドを有するものであれば特に限定されないが、ビスフェノールA、ビスフェノールF、ビスフェノールADや、ノボラック等を含みポリオキシアルキレン単位を有するエポキシ樹脂がより好適な例として挙げられる。 In order to improve water resistance, it is preferable to further add (F) an epoxy resin to the curable composition of the present invention. As the (F) epoxy resin, conventionally known epoxy resins can be widely used, and are not particularly limited. However, it is preferable to use a bisphenol type epoxy resin or an epoxy resin having a polyoxyalkylene skeleton. The epoxy resin having a polyoxyalkylene skeleton is not particularly limited as long as it has a polyalkylene oxide, but bisphenol A, bisphenol F, bisphenol AD, and an epoxy resin having a polyoxyalkylene unit including novolak and the like are more preferable. A suitable example is given.
該(F)エポキシ樹脂の配合割合は、成分(A)100重量部に対して、1〜200重量部用いることが好ましく、3〜150重量部が更に好適である。該エポキシ樹脂は単独で用いても良く、2種以上を併用しても良い。 The blending ratio of the (F) epoxy resin is preferably 1 to 200 parts by weight, and more preferably 3 to 150 parts by weight with respect to 100 parts by weight of the component (A). This epoxy resin may be used independently and may use 2 or more types together.
上記成分(F)エポキシ樹脂を添加する場合、該エポキシ樹脂に対する硬化剤(エポキシ樹脂硬化剤)として、ケチミン類等を添加することもできる。上記硬化剤は、単独で使用してもよく、2種以上併用してもよい。また、成分(A)に対し硬化触媒作用を示し且つエポキシ樹脂の硬化剤となりうるものを上記硬化触媒(D)及び硬化剤として用いることも無論可能である。 When adding the said component (F) epoxy resin, ketimines etc. can also be added as a hardening | curing agent (epoxy resin hardening | curing agent) with respect to this epoxy resin. The said hardening | curing agent may be used independently and may be used together 2 or more types. Of course, it is possible to use a curing catalyst for the component (A) and a curing agent for the epoxy resin as the curing catalyst (D) and the curing agent.
本発明の硬化性組成物は、上記した成分に加えて、必要に応じて、接着付与剤、物性調整剤、充填剤、可塑剤、揺変剤、脱水剤(保存安定性改良剤)、粘着付与剤、垂れ防止剤、紫外線吸収剤、酸化防止剤、難燃剤、着色剤、ラジカル重合開始剤などの物質やトルエンやアルコール等の各種溶剤を配合してもよく、また相溶する他の重合体をブレンドしてもよい。 In addition to the above-described components, the curable composition of the present invention includes an adhesion-imparting agent, a physical property modifier, a filler, a plasticizer, a thixotropic agent, a dehydrating agent (storage stability improving agent), and an adhesive as necessary. Substances such as imparting agents, anti-sagging agents, ultraviolet absorbers, antioxidants, flame retardants, colorants, radical polymerization initiators, and various solvents such as toluene and alcohol may be blended, and other compatible heavy components. The coalescence may be blended.
上記の相溶する他の重合体としては各種ポリエーテルが特に好ましく、とりわけ、特許文献4及び32〜35で提案されている珪素官能基を有するポリエーテルなどが挙げられる。 As the other compatible polymer, various polyethers are particularly preferable, and in particular, polyethers having a silicon functional group proposed in Patent Documents 4 and 32-35 and the like can be mentioned.
上記接着付与剤としては、各種シランカップリング剤、例えば、アミノエチルアミノプロピルトリメトキシシラン、アミノエチルアミノプロピルメチルジメトキシシラン、アミノエチルアミノプロピルメチルメトキシシランなどのアミノシラン類、γ−グリシドキシプロピルトリメトキシシランなどのエポキシシラン類、γ−メタクリロキシプロピルトリメトキシシランなどのアクリルシラン類、γ−メルカプトプロピルトリメトキシシランなどのメルカプトシラン類、γ−イソシアネートプロピルトリメトキシシランなどのイソシアネートシラン類などが挙げられる。上記接着付与剤は単独で用いても良く、2種以上併用しても良い。 Examples of the adhesion-imparting agent include various silane coupling agents such as aminosilanes such as aminoethylaminopropyltrimethoxysilane, aminoethylaminopropylmethyldimethoxysilane, aminoethylaminopropylmethylmethoxysilane, and γ-glycidoxypropyltrimethyl. Examples include epoxy silanes such as methoxysilane, acrylic silanes such as γ-methacryloxypropyltrimethoxysilane, mercaptosilanes such as γ-mercaptopropyltrimethoxysilane, and isocyanate silanes such as γ-isocyanatopropyltrimethoxysilane. It is done. The said adhesion grant agent may be used independently and may be used together 2 or more types.
上記物性調整剤は引っ張り物性を改善する目的で添加される。上記物性調整剤の例としては、1分子中にシラノール基を1個有するシリコン化合物があり、例えば、トリフェニルシラノール、トリアルキルシラノール、ジアルキルフェニルシラノール、ジフェニルアルキルシラノール等が挙げられ、その他にも加水分解して1分子中にシラノール基を1個有する化合物を生成するシリコン化合物等の各種シランカップリング剤が挙げられ、例えば、トリフェニルメトキシシラン、トリアルキルメトキシシラン、ジアルキルフェニルメトキシシラン、ジフェニルアルキルメトキシシラン、トリフェニルエトキシシラン、トリアルキルエトキシシラン等が挙げられる。上記物性調整剤は単独で用いても良く、2種以上併用しても良い。 The physical property modifier is added for the purpose of improving the tensile physical properties. Examples of the physical property adjusting agent include a silicon compound having one silanol group in one molecule, and examples thereof include triphenylsilanol, trialkylsilanol, dialkylphenylsilanol, diphenylalkylsilanol, and the like. Various silane coupling agents such as silicon compounds that can be decomposed to produce a compound having one silanol group in one molecule, such as triphenylmethoxysilane, trialkylmethoxysilane, dialkylphenylmethoxysilane, diphenylalkylmethoxy Silane, triphenylethoxysilane, trialkylethoxysilane, etc. are mentioned. The said physical property modifier may be used independently and may be used together 2 or more types.
上記充填剤は硬化物の補強の目的で添加される。上記充填剤として、例えば、炭酸カルシウム、炭酸マグネシウム、珪藻土含水ケイ酸、含水けい酸、無水ケイ酸、ケイ酸カルシウム、シリカ、二酸化チタン、クレー、タルク、カーボンブラック、スレート粉、マイカ、カオリン、ゼオライト等が挙げられ、このうち炭酸カルシウムが好ましく、脂肪酸処理炭酸カルシウムがより好ましい。また、ガラスビーズ、シリカビーズ、アルミナビーズ、カーボンビーズ、スチレンビーズ、フェノールビーズ、アクリルビーズ、多孔質シリカ、シラスバルーン、ガラスバルーン、シリカバルーン、サランバルーン、アクリルバルーン等を用いることもでき、これらの中で、組成物の硬化後の伸びの低下が少ない点からアクリルバルーンがより好ましい。上記充填剤は単独で用いても良く、2種以上併用しても良い。 The filler is added for the purpose of reinforcing the cured product. Examples of the filler include calcium carbonate, magnesium carbonate, diatomaceous earth hydrous silicic acid, hydrous silicic acid, anhydrous silicic acid, calcium silicate, silica, titanium dioxide, clay, talc, carbon black, slate powder, mica, kaolin, and zeolite. Of these, calcium carbonate is preferable, and fatty acid-treated calcium carbonate is more preferable. In addition, glass beads, silica beads, alumina beads, carbon beads, styrene beads, phenol beads, acrylic beads, porous silica, shirasu balloons, glass balloons, silica balloons, saran balloons, acrylic balloons, etc. can be used. Among them, an acrylic balloon is more preferable from the viewpoint that the decrease in elongation after curing of the composition is small. The said filler may be used independently and may be used together 2 or more types.
上記可塑剤は硬化後の伸び物性を高めたり、低モジュラス化を可能とする目的で添加される。本発明においては、上記(B)成分を可塑剤として用いることもできるが、必要に応じて、他の可塑剤を添加しても良い。他の可塑剤としては、例えば、リン酸トリブチル、リン酸トリクレジル等のリン酸エステル類;ジオクチルフタレート(DOP)、ジブチルフタレート、ブチルベンジルフタレートなどのフタル酸エステル類;グリセリンモノオレイン酸エステル等の脂肪酸一塩基酸エステル類;アジピン酸ジブチル、アジピン酸ジオクチル等の脂肪酸二塩基酸エステル類;ポリプロピレングリコール等のグリコールエステル類;脂肪族エステル類;エポキシ可塑剤類;ポリエステル系可塑剤;ポリエーテル類;ポリスチレン類などが挙げられる。上記可塑剤は単独で用いても良く、または、2種類以上を併用しても良い。 The plasticizer is added for the purpose of improving the elongation physical properties after curing or enabling low modulus. In the present invention, the component (B) can be used as a plasticizer, but other plasticizers may be added as necessary. Other plasticizers include, for example, phosphate esters such as tributyl phosphate and tricresyl phosphate; phthalate esters such as dioctyl phthalate (DOP), dibutyl phthalate, and butyl benzyl phthalate; fatty acids such as glycerin monooleate Monobasic acid esters; Fatty acid dibasic acid esters such as dibutyl adipate and dioctyl adipate; Glycol esters such as polypropylene glycol; Aliphatic esters; Epoxy plasticizers; Polyester plasticizers; Polyethers; And the like. The said plasticizer may be used independently or may use 2 or more types together.
上記揺変剤としては、例えば、コロイダルシリカ、石綿粉等の無機揺変剤、有機ベントナイト、変性ポリエステルポリオール、脂肪酸アマイド等の有機揺変剤、水添ヒマシ油誘導体、脂肪酸アマイドワックス、ステアリル酸アルミニウム、ステアリル酸バリウム等が挙げられる。上記揺変剤は単独で使用しても良く、または、2種類以上を併用しても良い。 Examples of the thixotropic agent include inorganic thixotropic agents such as colloidal silica and asbestos powder, organic thixotropic agents such as organic bentonite, modified polyester polyol, and fatty acid amide, hydrogenated castor oil derivative, fatty acid amide wax, and aluminum stearylate. And barium stearylate. The thixotropic agents may be used alone or in combination of two or more.
上記脱水剤は保存中における水分を除去する目的で添加される。上記脱水剤として、例えば、ビニルトリメトキシシラン、ジメトルジメトキシシラン、テトラエトキシシラン、メチルトリメトキシシラン、メチルトリエトキシシラン等のシラン化合物が挙げられる。 The dehydrating agent is added for the purpose of removing moisture during storage. Examples of the dehydrating agent include silane compounds such as vinyltrimethoxysilane, dimetholdimethoxysilane, tetraethoxysilane, methyltrimethoxysilane, and methyltriethoxysilane.
上記酸化防止剤は、硬化シーリング材の酸化を防止して、耐候性を改善するために使用されるものであり、例えば、ヒンダードアミン系やヒンダードフェノール系の酸化防止剤等が挙げられる。ヒンダードアミン系酸化防止剤としては、例えば、N,N′,N″,N″′−テトラキス−(4,6−ビス(ブチル−(N−メチル−2,2,6,6−テトラメチルピペリジン−4−イル)アミノ)−トリアジン−2−イル)−4,7−ジアザデカン−1,10−ジアミン、ジブチルアミン・1,3,5−トリアジン・N,N′−ビス−(2,2,6,6−テトラメチル−4−ピペリジル−1,6−ヘキサメチレンジアミン・N−(2,2,6,6−テトラメチル−4−ピペリジル)ブチルアミンの重縮合物、ポリ[{6−(1,1,3,3−テトラメチルブチル)アミノ−1,3,5−トリアジン−2,4−ジイル}{(2,2,6,6−テトラメチル−4−ピペリジル)イミノ}ヘキサメチレン{(2,2,6,6−テトラメチル−4−ピペリジル)イミノ}]、コハク酸ジメチルと4−ヒドロキシ−2,2,6,6−テトラメチル−1−ピペリジンエタノールの重合体、[デカン二酸ビス(2,2,6,6−テトラメチル−1(オクチルオキシ)−4−ピペリジル)エステル、1,1−ジメチルエチルヒドロペルオキシドとオクタンの反応生成物(70%)]−ポリプロピレン(30%)、ビス(1,2,2,6,6−ペンタメチル−4−ピペリジル)[[3,5−ビス(1,1−ジメチルエチル)−4−ヒドロキシフェニル]メチル]ブチルマロネート、メチル1,2,2,6,6−ペンタメチル−4−ピペリジルセバケート、ビス(2,2,6,6−テトラメチル−4−ピペリジル)セバケ−ト、ビス(1,2,2,6,6−ペンタメチル−4−ピペリジル)セバケ−ト、1−[2−〔3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオニルオキシ〕エチル]−4−〔3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオニルオキシ〕−2,2,6,6−テトラメチルピペリジン、4−ベンゾイルオキシ−2,2,6,6−テトラメチルピペリジン、8−アセチル−3−ドデシル−7,7,9,9−テトラメチル−1,3,8−トリアザスピロ[4.5]デカン−2,4−ジオンなどが挙げられるが、これらに限定されるものではない。ヒンダードフェノール系酸化防止剤としては、例えば、ペンタエリストール−テトラキス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート]、チオジエチレン−ビス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート]、オクタデシル−3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート]、N,N′−ヘキサン−1,6−ジイルビス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニルプロピオアミド]、ベンゼンプロパン酸3,5−ビス(1,1−ジメチルエチル)−4−ヒドロキシC7−C9側鎖アルキルエステル、2,4−ジメチル−6−(1−メチルペンタデシル)フェノール、ジエチル[[3,5−ビス(1,1−ジメチルエチル)−4−ヒドロキシフェニル]メチル]ホスホネート、3,3′,3″,5,5′,5″−ヘキサン−tert−ブチル−4−a,a′,a″−(メシチレン−2,4,6−トリル)トリ−p−クレゾール、カルシウムジエチルビス[[[3,5−ビス−(1,1−ジメチルエチル)−4−ヒドロキシフェニル]メチル]ホスホネート]、4,6−ビス(オクチルチオメチル)−o−クレゾール、エチレンビス(オキシエチレン)ビス[3−(5−tert−ブチル−4−ヒドロキシ−m−トリル)プロピオネート]、ヘキサメチレンビス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート]、1,3,5−トリス(3,5−ジ−tert−ブチル−4−ヒドロキシベンジル)−1,3,5−トリアジン−2,4,6−(1H,3H,5H)−トリオン、N−フェニルベンゼンアミンと2,4,4−トリメチルペンテンとの反応生成物、2,6−ジ−tert−ブチル−4−(4,6−ビス(オクチルチオ)−1,3,5−トリアジン−2−イルアミノ)フェノールなどが挙げられるが、これらに限定されるものではない。上記酸化防止剤は単独で使用しても良く、または、2種類以上を併用しても良い。 The said antioxidant is used in order to prevent the hardening sealing material from oxidizing and to improve the weather resistance, and examples thereof include hindered amine-based and hindered phenol-based antioxidants. Examples of the hindered amine antioxidant include N, N ′, N ″, N ″ ′-tetrakis- (4,6-bis (butyl- (N-methyl-2,2,6,6-tetramethylpiperidine- 4-yl) amino) -triazin-2-yl) -4,7-diazadecane-1,10-diamine, dibutylamine 1,3,5-triazine N, N'-bis- (2,2,6 , 6-tetramethyl-4-piperidyl-1,6-hexamethylenediamine · N- (2,2,6,6-tetramethyl-4-piperidyl) butylamine polycondensate, poly [{6- (1, 1,3,3-tetramethylbutyl) amino-1,3,5-triazine-2,4-diyl} {(2,2,6,6-tetramethyl-4-piperidyl) imino} hexamethylene {(2 , 2,6,6-tetramethyl-4- Peridyl) imino}], a polymer of dimethyl succinate and 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol, [bis (2,2,6,6-tetramethyl-decanedioic acid) 1 (octyloxy) -4-piperidyl) ester, reaction product of 1,1-dimethylethyl hydroperoxide and octane (70%)]-polypropylene (30%), bis (1,2,2,6,6- Pentamethyl-4-piperidyl) [[3,5-bis (1,1-dimethylethyl) -4-hydroxyphenyl] methyl] butyl malonate, methyl 1,2,2,6,6-pentamethyl-4-piperidyl seba Kate, bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate 1- [2- [3- (3,5-Di-tert-butyl-4-hydroxyphenyl) propionyloxy] ethyl] -4- [3- (3,5-di-tert-butyl-4-hydroxyphenyl) ) Propionyloxy] -2,2,6,6-tetramethylpiperidine, 4-benzoyloxy-2,2,6,6-tetramethylpiperidine, 8-acetyl-3-dodecyl-7,7,9,9- Examples include, but are not limited to, tetramethyl-1,3,8-triazaspiro [4.5] decane-2,4-dione, etc. Examples of hindered phenol antioxidants include pentane. Erythritol-tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], thiodiethylene-bis [3- (3,5-di-ter t-butyl-4-hydroxyphenyl) propionate], octadecyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], N, N′-hexane-1,6-diylbis [3- (3,5-di-tert-butyl-4-hydroxyphenylpropioamide), benzenepropanoic acid 3,5-bis (1,1-dimethylethyl) -4-hydroxy C7-C9 side chain alkyl ester, 2,4 -Dimethyl-6- (1-methylpentadecyl) phenol, diethyl [[3,5-bis (1,1-dimethylethyl) -4-hydroxyphenyl] methyl] phosphonate, 3,3 ', 3 ", 5 5 ', 5 "-hexane-tert-butyl-4-a, a', a"-(mesitylene-2,4,6-tolyl) tri-p-cresol, calci Mudiethylbis [[[3,5-bis- (1,1-dimethylethyl) -4-hydroxyphenyl] methyl] phosphonate], 4,6-bis (octylthiomethyl) -o-cresol, ethylenebis (oxyethylene) Bis [3- (5-tert-butyl-4-hydroxy-m-tolyl) propionate], hexamethylenebis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], 1,3 , 5-Tris (3,5-di-tert-butyl-4-hydroxybenzyl) -1,3,5-triazine-2,4,6- (1H, 3H, 5H) -trione, N-phenylbenzenamine Product of 2,4,4-trimethylpentene with 2,6-di-tert-butyl-4- (4,6-bis (octylthio) -1,3,5 Triazin-2-ylamino) phenol and the like, but not limited thereto. The said antioxidant may be used independently or may use 2 or more types together.
上記紫外線吸収剤は、硬化シーリング材の光劣化を防止して、耐候性を改善するために使用されるものであり、例えば、ベンゾトリアゾール系、トリアジン系、ベンゾフェノン系、ベンゾエート系等の紫外線吸収剤等が挙げられる。紫外線吸収剤としては、例えば、2,4−ジ−tert−ブチル−6−(5−クロロベンゾトリアゾール−2−イル)フェノール、2−(2H−ベンゾトリアゾール−2−イル)−4,6−ジ−tert−ペンチルフェノール、2−(2H−ベンゾトリアゾール−2−イル)−4−(1,1,3,3−テトラメチルブチル)フェノール、メチル3−(3−(2H−ベンゾトリアゾール−2−イル)−5−tert−ブチル−4−ヒドロキシフェニル)プロピオネート/ポリエチレングリコール300の反応生成物、2−(2H−ベンゾトリアゾール−2−イル)−6−(直鎖及び側鎖ドデシル)−4−メチルフェノール等のベンゾトリアゾール系紫外線吸収剤、2−(4,6−ジフェニル−1,3,5−トリアジン−2−イル)−5−[(ヘキシル)オキシ]−フェノール等のトリアジン系紫外線吸収剤、オクタベンゾン等のベンゾフェノン系紫外線吸収剤、2,4−ジ−tert−ブチルフェニル−3,5−ジ−tert−ブチル−4−ヒドロキシベンゾエート等のベンゾエート系紫外線吸収剤などが挙げられるが、これらに限定されるものではない。上記紫外線吸収剤は単独で使用してもよく、又は、2種類以上を併用しても良い。 The ultraviolet absorber is used for preventing the photo-degradation of the cured sealant and improving the weather resistance. For example, the ultraviolet absorber of benzotriazole, triazine, benzophenone, benzoate, etc. Etc. Examples of the ultraviolet absorber include 2,4-di-tert-butyl-6- (5-chlorobenzotriazol-2-yl) phenol and 2- (2H-benzotriazol-2-yl) -4,6- Di-tert-pentylphenol, 2- (2H-benzotriazol-2-yl) -4- (1,1,3,3-tetramethylbutyl) phenol, methyl 3- (3- (2H-benzotriazole-2) -Yl) -5-tert-butyl-4-hydroxyphenyl) propionate / polyethylene glycol 300 reaction product, 2- (2H-benzotriazol-2-yl) -6- (linear and side chain dodecyl) -4 -Benzotriazole ultraviolet absorbers such as methylphenol, 2- (4,6-diphenyl-1,3,5-triazin-2-yl) -5-[(he Sil) oxy] -phenol and the like triazine ultraviolet absorbers, benzophenone ultraviolet absorbers such as octabenzone, 2,4-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate, etc. Examples include, but are not limited to, benzoate ultraviolet absorbers. The said ultraviolet absorber may be used independently or may use 2 or more types together.
本硬化性組成物の第2の態様は、成分(A1)架橋性シリル基含有アクリル系重合体、成分(C)水と反応してアミン化合物を生成する化合物、及び成分(D)硬化触媒を含有することを特徴とする。上記成分(A1)、(C)及び(D)は、本発明の硬化性組成物の第1の態様において上述した通りである。また、各成分の配合割合も上記した本発明の硬化性組成物の第1の態様と同様に行えばよい。必要に応じて上記したような可塑剤を添加しても良い。上記成分以外の配合物についても同様である。 The second aspect of the present curable composition comprises component (A1) a crosslinkable silyl group-containing acrylic polymer, component (C) a compound that reacts with water to form an amine compound, and component (D) a curing catalyst. It is characterized by containing. The components (A1), (C) and (D) are as described above in the first embodiment of the curable composition of the present invention. Moreover, what is necessary is just to perform the mixture ratio of each component similarly to the 1st aspect of the above-mentioned curable composition of this invention. You may add the above plasticizers as needed. The same applies to blends other than the above components.
本発明の硬化性組成物は、必要に応じて1液型とすることもできるし、2液型とすることもできるが、特に1液型として好適に用いることができる。本発明の硬化性組成物は、シーリング材、接着剤及びコーティング材等として好適に用いられる。本発明の硬化性組成物は、基本性能を損なうことなく、優れた耐候性及び意匠性を有しているため、特に、外壁材のシーリングに用いることが好ましいが、その他各種建築物用、自動車用、土木用、電気・電子分野用等に使用することができる。 The curable composition of the present invention can be a one-component type or a two-component type as required, but can be suitably used particularly as a one-component type. The curable composition of the present invention is suitably used as a sealing material, an adhesive, a coating material, and the like. Since the curable composition of the present invention has excellent weather resistance and design without impairing basic performance, it is particularly preferably used for sealing outer wall materials. It can be used for civil engineering, civil engineering, and electric / electronic fields.
以下に本発明の実施例を挙げてさらに具体的に説明するが、この実施例は例示的に示されるもので、限定的に解釈されるべきでないことはいうまでもない。 The present invention will be described more specifically with reference to the following examples. However, it is needless to say that the examples are shown by way of example and should not be interpreted in a limited manner.
(合成例1及び2)
表1に示した配合物質及び配合量(g)にて合成を行った。加熱装置及びエステル管付き攪拌容器に、加熱溶解した第1級アミンを入れた後、攪拌しながらカルボニル化合物を加えた。この中に更にトルエンを加えたのち加温して110〜150℃で3時間攪拌を続けて、エステル管により水を脱水した。次いで減圧して、過剰のカルボニル化合物及びトルエンを除去して、ケチミン化合物を得た。
(Synthesis Examples 1 and 2)
The synthesis was performed using the compounding substances and the compounding amount (g) shown in Table 1. The primary amine dissolved by heating was placed in a heating apparatus and a stirring vessel equipped with an ester tube, and then the carbonyl compound was added with stirring. Toluene was further added thereto, followed by heating and stirring at 110 to 150 ° C. for 3 hours, and water was dehydrated through an ester tube. Subsequently, the pressure was reduced to remove excess carbonyl compound and toluene to obtain a ketimine compound.
表1における各配合物質の配合量は(g)で示され、*1〜*3は次の通りである。
*1:ステアリルアミン(花王(株)製、ファーミン80、アミン価207)
*2:ヘキサメチレンジアミン(分子量:116)
*3:メチルイソブチルケトン(4−メチル−2−ペンタノン、分子量:100.2)
The amount of each compounding substance in Table 1 is indicated by (g), and * 1 to * 3 are as follows.
* 1: Stearylamine (Kao Co., Ltd., Farmin 80, amine value 207)
* 2: Hexamethylenediamine (molecular weight: 116)
* 3: Methyl isobutyl ketone (4-methyl-2-pentanone, molecular weight: 100.2)
(合成例3)
架橋性シリル基含有アクリル系重合体(A1)として、下記方法に基づき、架橋性シリル基含有アクリル酸エステル−フルオロオレフィン共重合体を合成した。撹拌機を備えた2リットルのオートクレーブに、有機溶媒として酢酸ブチル135gおよびエタノール75g、単量体としてアクリル酸ブチルエステル6.9g、アクリル酸2−メトキシエチルエステル7.0gおよびビニルトリメトキシシラン1.0g、ならびにラジカル重合開始剤としてエトキシエチルパーオキシジカーボネート4.0gを仕込み、脱気と窒素置換を3回繰り返した後減圧脱気し、クロロトリフルオロエチレン510gを仕込んだ。50℃まで昇温して重合を開始させ、昇温1時間後、アクリル酸ブチルエステル62.4g、アクリル酸2−メトキシエチルエステル63.0gおよびビニルトリメトキシシラン9.0gの混合液を7時間に渡り一定速度でポンプを用いてオートクレーブ中に送り込んだ。重合開始8時間経過後、60℃まで昇温し重合を計10時間行った後、冷却した。反応終了後、未反応のクロロトリフルオロエチレンをパージし、オートクレーブを開放して共重合体溶液を得た。得られた溶液を濾過しほう酸ソーダを除いた後減圧乾燥させ、メタノール中に投入し、洗浄乾燥し245gの共重合体を得た。
(Synthesis Example 3)
As the crosslinkable silyl group-containing acrylic polymer (A1), a crosslinkable silyl group-containing acrylic acid ester-fluoroolefin copolymer was synthesized based on the following method. In a 2 liter autoclave equipped with a stirrer, 135 g of butyl acetate and 75 g of ethanol as an organic solvent, 6.9 g of butyl acrylate, 7.0 g of 2-methoxyethyl acrylate, and vinyltrimethoxysilane 1. 0 g and 4.0 g of ethoxyethyl peroxydicarbonate as a radical polymerization initiator were charged, degassing and nitrogen substitution were repeated three times, then degassing under reduced pressure, and 510 g of chlorotrifluoroethylene was charged. The temperature was raised to 50 ° C. to initiate polymerization, and after raising the temperature for 1 hour, a mixed solution of 62.4 g of butyl acrylate, 63.0 g of 2-methoxyethyl acrylate and 9.0 g of vinyltrimethoxysilane was added for 7 hours. The mixture was fed into the autoclave using a pump at a constant speed. After 8 hours from the start of polymerization, the temperature was raised to 60 ° C. and polymerization was carried out for a total of 10 hours, followed by cooling. After completion of the reaction, unreacted chlorotrifluoroethylene was purged and the autoclave was opened to obtain a copolymer solution. The obtained solution was filtered to remove sodium borate and then dried under reduced pressure, put into methanol, washed and dried to obtain 245 g of a copolymer.
(合成例4)
攪拌機を備えた2L耐圧オートクレーブに、2−プロパノールを200質量部仕込んだ。次に、脱気と窒素置換を3回繰り返した後減圧脱気し、260℃まで加熱した。昇温が完了した時点で、アクリル酸エステル単量体としてアクリル酸ブチル750質量部、アクリル酸エチル130質量部とし、γ−メタクリロキシプロピルトリメトキシシラン120質量部、2−プロパノール200質量部、ジターシャリーブチルパーオキサイド10質量部からなる混合液を一定の速度でオートクレーブ中に供給し、反応を開始した。2時間かけて添加、反応を行い、添加終了10分後に30℃まで冷却し、平均して1分子中に0.72個の架橋性シリル基を有する架橋性シリル基含有アクリル系重合体(B)を得た。得られた重合体の質量平均分子量は3500であった。
(Synthesis Example 4)
200 parts by mass of 2-propanol was charged into a 2 L pressure-resistant autoclave equipped with a stirrer. Next, degassing and nitrogen substitution were repeated three times, followed by degassing under reduced pressure and heating to 260 ° C. When the temperature increase is completed, 750 parts by mass of butyl acrylate and 130 parts by mass of ethyl acrylate as the acrylate monomer, 120 parts by mass of γ-methacryloxypropyltrimethoxysilane, 200 parts by mass of 2-propanol, diter A liquid mixture consisting of 10 parts by mass of shary butyl peroxide was fed into the autoclave at a constant rate to initiate the reaction. Added and reacted over 2 hours, cooled to 30 ° C. 10 minutes after completion of addition, and on average a crosslinkable silyl group-containing acrylic polymer having 0.72 crosslinkable silyl groups in one molecule (B ) The obtained polymer had a weight average molecular weight of 3,500.
(実施例1)
表2に示したように、成分(A)架橋性シリル基含有有機重合体として架橋性シリル基含有ポリオキシプロピレン重合体、成分(B)アクリル系重合体として水酸基非含有アクリル系重合体、老化防止剤、炭酸カルシウム及びビニルトリメトキシシランをそれぞれ所定量ずつ仕込み、加熱減圧混合攪拌を110℃にて2時間行い、配合物質の脱水を行った。さらに、成分(C)水と反応してアミン化合物を生成する化合物として上記合成例1で得たケチミン化合物、成分(D)硬化触媒としてジブチル錫ジアセチルアセトナート、及び成分(E1)アミノシラン化合物を所定量ずつ添加し、攪拌配合して硬化性組成物を調製した。
Example 1
As shown in Table 2, crosslinkable silyl group-containing polyoxypropylene polymer as component (A) crosslinkable silyl group-containing organic polymer, hydroxyl group-free acrylic polymer as component (B) acrylic polymer, aging A predetermined amount of each of the inhibitor, calcium carbonate, and vinyltrimethoxysilane was charged, and the mixture was heated and vacuum mixed and stirred at 110 ° C. for 2 hours to dehydrate the compounded material. Further, the component (C) is a ketimine compound obtained in Synthesis Example 1 as a compound that reacts with water to form an amine compound, the component (D) is dibutyltin diacetylacetonate as a curing catalyst, and the component (E1) is an aminosilane compound. A curable composition was prepared by adding a fixed amount and mixing by stirring.
表2における各配合物質の配合量は(g)で示され、*1及び*3は表1と同じであり、*4〜*17は次の通りである。
*4:架橋性シリル基含有ポリオキシプロピレン重合体(鐘淵化学工業(株)製、商品名:MSポリマーS303)
*5:架橋性シリル基含有アクリル変性ポリオキシプロピレン重合体(鐘淵化学工業(株)製、商品名:MSポリマーS903)
*6:合成例3で得た架橋性シリル基含有アクリル系重合体
*7:水酸基非含有アクリル系重合体(東亞合成(株)製、商品名:UP−1110)
*8:水酸基含有アクリル系重合体(東亞合成(株)製、商品名:UH−2000)
*9:アクリル酸エステル−フルオロオレフィン共重合体(東亞合成(株)製、商品名:XCS−3500)
*10:合成例4で得た架橋性シリル基含有アクリル系重合体
*11:合成例1で得たケチミン化合物
*12:合成例2で得たケチミン化合物
*13:ジブチル錫ジアセチルアセトナート
*14:ケチミン構造含有アミノシラン(信越化学工業(株)製、商品名:X12−817)
*15:γ−アミノプロピルトリメトキシシラン
*16:チバ・スペシャルティ・ケミカルズ(株)製の老化防止剤、商品名:チヌビンB75
*17:脂肪酸処理炭酸カルシウム(丸尾カルシウム(株)製、商品名:カルファイン200M)
The amount of each compounding substance in Table 2 is indicated by (g), * 1 and * 3 are the same as in Table 1, and * 4 to * 17 are as follows.
* 4: Crosslinkable silyl group-containing polyoxypropylene polymer (manufactured by Kaneka Chemical Co., Ltd., trade name: MS polymer S303)
* 5: Crosslinkable silyl group-containing acrylic modified polyoxypropylene polymer (manufactured by Kaneka Chemical Co., Ltd., trade name: MS polymer S903)
* 6: Crosslinkable silyl group-containing acrylic polymer obtained in Synthesis Example 3 * 7: Hydroxyl-free acrylic polymer (trade name: UP-1110, manufactured by Toagosei Co., Ltd.)
* 8: Hydroxyl group-containing acrylic polymer (manufactured by Toagosei Co., Ltd., trade name: UH-2000)
* 9: Acrylic ester-fluoroolefin copolymer (manufactured by Toagosei Co., Ltd., trade name: XCS-3500)
* 10: Crosslinkable silyl group-containing acrylic polymer obtained in Synthesis Example 4 * 11: Ketimine compound obtained in Synthesis Example 1 * 12: Ketimine compound obtained in Synthesis Example 2 * 13: Dibutyltin diacetylacetonate * 14 : Ketimine structure-containing aminosilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name: X12-817)
* 15: γ-aminopropyltrimethoxysilane * 16: Anti-aging agent manufactured by Ciba Specialty Chemicals Co., Ltd., trade name: Tinuvin B75
* 17: Fatty acid-treated calcium carbonate (Maruo Calcium Co., Ltd., trade name: Calfine 200M)
(実験例1及び実施例2、3)
表2に示したように、水酸基非含有アクリル系重合体の代わりに水酸基含有アクリル系重合体(実験例1)、アクリル酸エステル−フルオロオレフィン共重合体(実施例2)又は合成例4で得た架橋性シリル基含有アクリル系重合体(実施例3)を配合した以外は、実施例1と同様の方法により硬化性組成物を調製した。
( Experimental example 1 and Example 2 , 3 )
As shown in Table 2, a hydroxyl group-containing acrylic polymer ( Experimental Example 1 ), an acrylate-fluoroolefin copolymer (Example 2 ) or Synthesis Example 4 was obtained instead of the hydroxyl group-free acrylic polymer. A curable composition was prepared in the same manner as in Example 1 except that the crosslinkable silyl group-containing acrylic polymer (Example 3 ) was added.
(実施例4)
表2に示したように、合成例1で得たケチミン化合物の代わりに上記合成例2で得たケチミン化合物を配合した以外は、実施例1と同様の方法により硬化性組成物を調製した。
(Example 4 )
As shown in Table 2, a curable composition was prepared in the same manner as in Example 1 except that the ketimine compound obtained in Synthesis Example 2 was blended instead of the ketimine compound obtained in Synthesis Example 1.
(実施例5)
表2に示したように、架橋性シリル基含有ポリオキシプロピレン重合体の代わりに(A1)架橋性シリル基含有アクリル変性ポリオキシプロピレン重合体を配合した以外は、実施例1と同様の方法により硬化性組成物を調製した。
(Example 5 )
As shown in Table 2, in the same manner as in Example 1 except that (A1) a crosslinkable silyl group-containing acrylic modified polyoxypropylene polymer was blended instead of the crosslinkable silyl group-containing polyoxypropylene polymer. A curable composition was prepared.
(実施例6及び7)
表2に示したように、アミノシラン化合物の代わりに、成分(E)水と反応して一分子中に少なくとも一個のアルコキシシリル基を有するアミン化合物を生成する化合物としてケチミン構造含有アミノシランを配合した以外は、実施例1又は5と同様の方法により硬化性組成物を調製した。
(Examples 6 and 7 )
As shown in Table 2, in place of the aminosilane compound, the component (E) except that ketimine structure-containing aminosilane was added as a compound that reacts with water to produce an amine compound having at least one alkoxysilyl group in one molecule. Prepared a curable composition by the same method as in Example 1 or 5 .
(実施例8)
表2に示したように、架橋性シリル基含有ポリオキシプロピレン重合体の代わりに合成例3で得た(A1)架橋性シリル基含有アクリル系重合体を配合した以外は、実施例5と同様の方法により硬化性組成物を調製した。
(Example 8 )
As shown in Table 2, it was the same as Example 5 except that (A1) the crosslinkable silyl group-containing acrylic polymer obtained in Synthesis Example 3 was blended in place of the crosslinkable silyl group-containing polyoxypropylene polymer. A curable composition was prepared by the method.
(実験例2)
表2に示したように、成分(A1)架橋性シリル基含有アクリル系重合体として上記合成例3で得た共重合体、老化防止剤、炭酸カルシウム、ビニルトリメトキシシラン及びジオクチルフタレートをそれぞれ所定量ずつ仕込み、加熱減圧混合攪拌を110℃にて2時間行い、配合物質の脱水を行った。さらに、成分(C)として上記合成例1で得たケチミン化合物、成分(D)としてジブチル錫ジアセチルアセトナート及び成分(E1)アミノシラン化合物を添加し、攪拌配合して硬化性組成物を調製した。
(Experimental example 2 )
As shown in Table 2, as the component (A1) crosslinkable silyl group-containing acrylic polymer, the copolymer obtained in Synthesis Example 3 above, the antioxidant, calcium carbonate, vinyltrimethoxysilane, and dioctyl phthalate were placed. A fixed amount was charged and mixed under heating and reduced pressure at 110 ° C. for 2 hours to dehydrate the compounded material. Furthermore, the ketimine compound obtained in Synthesis Example 1 as component (C), dibutyltin diacetylacetonate and component (E1) aminosilane compound as component (D) were added, and the mixture was stirred to prepare a curable composition.
(実験例3)
表2に示したように、成分(A1)として、合成例3で得た共重合体100重量部の代わりに、合成例3で得た共重合体70重量部及び架橋性シリル基含有ポリオキシプロピレン重合体30重量部を配合した以外は、実験例2と同様の方法により、硬化性組成物を調製した。
(Experimental example 3 )
As shown in Table 2, as component (A1), instead of 100 parts by weight of the copolymer obtained in Synthesis Example 3, 70 parts by weight of the copolymer obtained in Synthesis Example 3 and a crosslinkable silyl group-containing polyoxy A curable composition was prepared in the same manner as in Experimental Example 2 , except that 30 parts by weight of the propylene polymer was blended.
(実験例4)
表2に示したように、合成例1で得たケチミン化合物及びケチミン構造含有アミノシランの代わりに、第1級アミン、カルボニル化合物、及びアミノシラン化合物を配合した以外は、実施例7と同様の方法により、硬化性組成物を調製した。
(Experimental example 4 )
As shown in Table 2, in place of the ketimine compound and ketimine structure-containing aminosilane obtained in Synthesis Example 1, a primary amine, a carbonyl compound, and an aminosilane compound were blended in the same manner as in Example 7. A curable composition was prepared.
(実験例5)
表2に示したように、合成例1で得たケチミン化合物の代わりに、第1級アミン及びカルボニル化合物を配合した以外は、実験例2と同様の方法により、硬化性組成物を調製した。
(Experimental example 5 )
As shown in Table 2, a curable composition was prepared in the same manner as in Experimental Example 2 , except that a primary amine and a carbonyl compound were blended in place of the ketimine compound obtained in Synthesis Example 1.
(比較例1)
表2に示したように、水酸基非含有アクリル系重合体及び合成例1より得たケチミン化合物を配合せず、代わりにジオクチルフタレート及び第1級アミンを配合した以外は、実施例1と同様の方法により硬化性組成物を調製した。
(Comparative Example 1)
As shown in Table 2, it was the same as Example 1 except that the hydroxyl group-free acrylic polymer and the ketimine compound obtained from Synthesis Example 1 were not blended, and dioctyl phthalate and primary amine were blended instead. A curable composition was prepared by the method.
(比較例2)
表2に示したように、合成例1より得たケチミン化合物の代わりに第1級アミンを配合した以外は、実施例1と同様の方法により硬化性組成物を調製した。
(Comparative Example 2)
As shown in Table 2, a curable composition was prepared in the same manner as in Example 1 except that a primary amine was blended in place of the ketimine compound obtained from Synthesis Example 1.
[性能試験]
実施例1〜8、実験例1〜5及び比較例1、2にて得られた硬化性組成物について、下記の性能試験を行った。なお、50℃で28日間及び56日間は、常温(20℃)で6〜8ヶ月及び12〜16ヶ月に相当する。各性能の測定結果を表3に示す。
[performance test]
The following performance tests were performed on the curable compositions obtained in Examples 1 to 8 , Experimental Examples 1 to 5 and Comparative Examples 1 and 2. In addition, 28 days and 50 days at 50 ° C. correspond to 6 to 8 months and 12 to 16 months at room temperature (20 ° C.). Table 3 shows the measurement results of each performance.
1)表面特性
上記得られた(製造直後及び50℃で28日間、56日間保存後の)硬化性組成物をシート状に硬化させ、23℃、50%相対湿度で7日間養生させて、厚み5mmのシートを作製した。このシートの表面の艶を目視により判定し、表面光沢度は60度鏡面光沢度計を使用して測定した。結果を表3に示す。なお、表面光沢度の数値が小さいほど光の反射率が低く、表面の艶が低下していることを示す。
1) Surface characteristics The curable composition obtained above (immediately after production and after storage for 28 days at 50 ° C. for 56 days) is cured into a sheet and cured for 7 days at 23 ° C. and 50% relative humidity to obtain a thickness. A 5 mm sheet was prepared. The gloss of the surface of this sheet was visually determined, and the surface gloss was measured using a 60-degree specular gloss meter. The results are shown in Table 3. In addition, it shows that the reflectance of light is so low that the numerical value of surface glossiness is low, and the glossiness of the surface is falling.
上記得られた(製造直後及び50℃で28日間、56日間保存後の)硬化性組成物の汚染性について、以下の方法にて調べた。厚さ5mmのスレート板を使用し、深さ5mm、幅25mm、長さ150mmの目地を作製し、その目地に硬化性組成物を打設し、余分の硬化性組成物をヘラでかきとり、表面を平らにしたものを、23℃、50%相対湿度で7日間養生し試験体を作製した。養生後の試験体の表面に黒色珪砂(粒径70〜110μm)をふりかけ、直ちに試験体を裏返し、底面を手で軽く叩き余分の黒色珪砂を落とした。表面に付着して残った黒色珪砂(汚れ)の状態を目視により観察し、養生後の汚染性を判定した。結果を表3に示す。 Contamination property of the obtained curable composition (immediately after production and after storage for 28 days at 50 ° C. for 56 days) was examined by the following method. Using a slate plate with a thickness of 5 mm, a joint having a depth of 5 mm, a width of 25 mm, and a length of 150 mm is prepared, a curable composition is placed on the joint, and the excess curable composition is scraped off with a spatula. Was flattened at 23 ° C. and 50% relative humidity for 7 days to prepare a test specimen. Black quartz sand (particle size: 70 to 110 μm) was sprinkled on the surface of the test specimen after curing, and the specimen was immediately turned over, and the bottom was lightly tapped by hand to remove excess black silica sand. The state of black silica sand (dirt) remaining on the surface was visually observed to determine the contamination after curing. The results are shown in Table 3.
2)引張接着性
JIS A1439:1997「建築用シーリング材の試験方法」の「4.21引張接着性試験」に準拠して試験した(試験温度23℃)。なお、試験体は、上記得られた(製造直後及び50℃で28日間、56日間保存後の)硬化性組成物を被着体としてアルマイトアルミに打設した試験体を23℃、50%相対湿度で14日間、30℃で14日間養生して作製した。また、耐水接着性については、上記条件にて作成された試験体を23℃水中に7日間浸漬したのちの破壊状態を評価し、接着性として示した。結果を表3に示す。
接着性の判定基準:◎;凝集破壊、○;薄層凝集破壊が確認される場合、△;界面破壊が確認される場合。
2) Tensile adhesiveness Tested in accordance with "4.21 Tensile adhesiveness test" of JIS A1439: 1997 "Testing method for architectural sealing material" (test temperature: 23 ° C). In addition, the test body was prepared by placing the above-obtained curable composition (immediately after production and after storage for 28 days at 50 ° C. for 56 days) on anodized aluminum as an adherend at 23 ° C. and 50% relative It was prepared by curing for 14 days at humidity and 14 days at 30 ° C. Moreover, about water-resistant adhesiveness, after destroying the test body created on the said conditions for 7 days in 23 degreeC water, the destruction state was evaluated and it showed as adhesiveness. The results are shown in Table 3.
Judgment criteria for adhesion: A: Cohesive failure, O: When thin layer cohesive failure is confirmed, Δ: When interface fracture is confirmed.
3)指触乾燥時間保持率
JIS A 1439 4.19により指触乾燥時間を測定した。判定方法は測定した結果の50℃で28日又は56日間保存後/製造直後が1.3未満を◎、1.3以上1.6未満を○、1.6以上1.9未満を△、1.9以上を×とした。結果を表3に示す。
3) Retention time of touch touch drying time Touch dry time was measured according to JIS A 1439 4.19. Judgment method is measured results at 50 ° C. for 28 days or 56 days after storage / immediately after production is less than 1.3, ◯ is 1.3 or more and less than 1.6, 1.6 or more and less than 1.9 is Δ, 1.9 or more was set as x. The results are shown in Table 3.
4)ゴム硬度保持率
23℃50%相対湿度雰囲気下24時間経過したものを試験体とし、厚さが5mm以上になるように積み重ね、JIS K 6301 5.2 スプリング式硬さ試験機A形を用いて測定した。判定方法は測定した結果の28日又は56日間保存後/製造直後が0.5未満を×、0.5以上0.7未満を△、0.7以上0.9未満を○、0.9以上1.0以下を◎とした。結果を表3に示す。
4) Rubber hardness retention rate 23 hours at 50 ° C. and a relative humidity atmosphere for 24 hours are used as test specimens, stacked so that the thickness is 5 mm or more, and JIS K 6301 5.2 spring type hardness tester A type And measured. The determination method is 28 days or 56 days of the measurement result after storage / immediately after production is less than 0.5 x, 0.5 to less than 0.7 Δ, 0.7 to less than 0.9 ○, 0.9 A value of 1.0 or less was evaluated as “◎”. The results are shown in Table 3.
5)耐候性
JIS K6266:1996に準じてサンシャインウエザオメーターを用いて1000時間後、2000時間後、3000時間後、5000時間後、7000時間後のシーリング材の表面の状態を目視により判定した。結果を表4に示す。
判定基準:○;シーリング材表面にヘアクラックなし、△;シーリング材表面にヘアクラック若干あり、×;シーリング材表面にヘアクラック多数あり。
5) Weather resistance According to JIS K6266: 1996, the state of the surface of the sealing material was visually determined after 1000 hours, 2000 hours, 3000 hours, 5000 hours, and 7000 hours using a sunshine weatherometer. The results are shown in Table 4.
Criteria: ○: No hair cracks on the surface of the sealing material, Δ: Some hair cracks on the surface of the sealing material, ×: Many hair cracks on the surface of the sealing material.
表3に示すように、実施例1〜8及び実験例1〜5の表面特性は、表面の艶、光沢性、汚染性、接着性について、製造直後及び50℃で28日間及び56日間保存後共に良好な結果が得られた。成分(E)が配合されている実施例7〜9並びに成分(E1)及び(E2)が配合されている実験例4及び5では、50℃で28日間及び56日間保存後の接着性、特に耐水試験後の接着性が改善されており、且つ製造直後の指触乾燥時間及びゴム硬度が50℃で28日間及び56日間保存後も維持されていた。一方、成分(C)が配合されていない比較例2では、製造直後の表面特性に問題はなかったが、50℃で28日間及び56日間保存後には表面の艶や汚染性が生じ、光沢度も増していた。また、表4に示した如く、実施例1〜8及び実験例1〜5は、比較例1に比べ耐候性が向上していた。実施例5及び実施例7〜8及び実験例2〜5は特に耐候性が向上していた。 As shown in Table 3, the surface properties of Examples 1 to 8 and Experimental Examples 1 to 5 are as follows: surface gloss, gloss, contamination, adhesion, immediately after production and after storage at 50 ° C. for 28 days and 56 days. Both obtained good results. In Examples 7 to 9 in which the component (E) is blended and in Experimental Examples 4 and 5 in which the components (E1) and (E2) are blended, the adhesiveness after storage at 50 ° C. for 28 days and 56 days, particularly The adhesiveness after the water resistance test was improved, and the touch drying time and rubber hardness immediately after production were maintained after storage at 50 ° C. for 28 days and 56 days. On the other hand, in Comparative Example 2 in which component (C) was not blended, there was no problem in the surface characteristics immediately after production, but gloss and contamination of the surface occurred after storage at 50 ° C. for 28 days and 56 days, and glossiness. It was also increasing. Further, as shown in Table 4, the weather resistance of Examples 1 to 8 and Experimental Examples 1 to 5 was improved as compared with Comparative Example 1. Example 5 and Examples 7 to 8 and Experimental Examples 2 to 5 were particularly improved in weather resistance.
Claims (7)
(B)アクリル系重合体、
(C)水と反応してアミン化合物を生成する化合物、及び
(D)硬化触媒を含有し、
前記成分(B)が、水酸基非含有アクリル系重合体及び/又は0.05個以上1.0個以下の架橋性シリル基を含有するアクリル系重合体であり、
前記成分(A)が、架橋性シリル基含有ポリオキシアルキレン系重合体、架橋性シリル基含有アクリル変性ポリオキシアルキレン系重合体、及び/又は架橋性シリル基含有メタクリル変性ポリオキシアルキレン系重合体であることを特徴とする硬化性組成物。 (A) a crosslinkable silyl group-containing organic polymer,
(B) an acrylic polymer,
(C) a compound that reacts with water to form an amine compound, and (D) a curing catalyst,
The component (B), Ri acrylic polymer der containing a hydroxyl group non-containing acrylic polymer and / or 0.05 or more 1.0 or less crosslinkable silyl group,
The component (A) is a crosslinkable silyl group-containing polyoxyalkylene polymer, a crosslinkable silyl group-containing acrylic modified polyoxyalkylene polymer, and / or a crosslinkable silyl group-containing methacryl-modified polyoxyalkylene polymer. curable composition characterized in that there.
(B)アクリル系重合体、
(C)水と反応してアミン化合物を生成する化合物、及び
(D)硬化触媒を含有し、
前記成分(B)が、水酸基非含有アクリル系重合体及び/又は0.05個以上1.0個以下の架橋性シリル基を含有するアクリル系重合体であり、
前記成分(A)が、(A1)架橋性シリル基含有アクリル系重合体であることを特徴とする硬化性組成物。 (A) a crosslinkable silyl group-containing organic polymer,
(B) an acrylic polymer,
(C) a compound that reacts with water to form an amine compound, and (D) a curing catalyst,
The component (B), Ri acrylic polymer der containing a hydroxyl group non-containing acrylic polymer and / or 0.05 or more 1.0 or less crosslinkable silyl group,
The said component (A) is (A1) crosslinkable silyl group containing acrylic polymer, The curable composition characterized by the above-mentioned.
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