JP5667854B2 - 1 component composition - Google Patents
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- JP5667854B2 JP5667854B2 JP2010268237A JP2010268237A JP5667854B2 JP 5667854 B2 JP5667854 B2 JP 5667854B2 JP 2010268237 A JP2010268237 A JP 2010268237A JP 2010268237 A JP2010268237 A JP 2010268237A JP 5667854 B2 JP5667854 B2 JP 5667854B2
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- 239000000203 mixture Substances 0.000 title claims description 39
- 229920006243 acrylic copolymer Polymers 0.000 claims description 34
- -1 mercaptosilane compound Chemical class 0.000 claims description 23
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 23
- 239000000178 monomer Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000012024 dehydrating agents Substances 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- RWLDCNACDPTRMY-UHFFFAOYSA-N 3-triethoxysilyl-n-(3-triethoxysilylpropyl)propan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCNCCC[Si](OCC)(OCC)OCC RWLDCNACDPTRMY-UHFFFAOYSA-N 0.000 claims description 4
- TZZGHGKTHXIOMN-UHFFFAOYSA-N 3-trimethoxysilyl-n-(3-trimethoxysilylpropyl)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCCC[Si](OC)(OC)OC TZZGHGKTHXIOMN-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 150000003606 tin compounds Chemical class 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 230000009477 glass transition Effects 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 19
- 238000000576 coating method Methods 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 238000003860 storage Methods 0.000 description 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 239000006087 Silane Coupling Agent Substances 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000565 sealant Substances 0.000 description 4
- 230000008719 thickening Effects 0.000 description 4
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000005233 alkylalcohol group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-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
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 239000004567 concrete Substances 0.000 description 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 2
- IESWIBSMHJCJAG-UHFFFAOYSA-L dibutyltin(2+);8-methyl-2-(6-methylheptyl)-2-sulfanylnonanoate Chemical compound CCCC[Sn+2]CCCC.CC(C)CCCCCC(S)(C([O-])=O)CCCCCC(C)C.CC(C)CCCCCC(S)(C([O-])=O)CCCCCC(C)C IESWIBSMHJCJAG-UHFFFAOYSA-L 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000007665 sagging Methods 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000035882 stress Effects 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- NQQRXZOPZBKCNF-NSCUHMNNSA-N (e)-but-2-enamide Chemical compound C\C=C\C(N)=O NQQRXZOPZBKCNF-NSCUHMNNSA-N 0.000 description 1
- BSSNZUFKXJJCBG-OWOJBTEDSA-N (e)-but-2-enediamide Chemical compound NC(=O)\C=C\C(N)=O BSSNZUFKXJJCBG-OWOJBTEDSA-N 0.000 description 1
- BSSNZUFKXJJCBG-UPHRSURJSA-N (z)-but-2-enediamide Chemical compound NC(=O)\C=C/C(N)=O BSSNZUFKXJJCBG-UPHRSURJSA-N 0.000 description 1
- FQJMHCIJFGVJAA-UHFFFAOYSA-N 1,1,1-triethoxy-2-methylpropane Chemical compound CCOC(OCC)(OCC)C(C)C FQJMHCIJFGVJAA-UHFFFAOYSA-N 0.000 description 1
- KOPMZTKUZCNGFY-UHFFFAOYSA-N 1,1,1-triethoxybutane Chemical compound CCCC(OCC)(OCC)OCC KOPMZTKUZCNGFY-UHFFFAOYSA-N 0.000 description 1
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
- FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 1
- BGLARIMANCDMQX-UHFFFAOYSA-N 1,1,1-trimethoxy-2-methylpropane Chemical compound COC(OC)(OC)C(C)C BGLARIMANCDMQX-UHFFFAOYSA-N 0.000 description 1
- ZGMNAIODRDOMEK-UHFFFAOYSA-N 1,1,1-trimethoxypropane Chemical compound CCC(OC)(OC)OC ZGMNAIODRDOMEK-UHFFFAOYSA-N 0.000 description 1
- MJYFYGVCLHNRKB-UHFFFAOYSA-N 1,1,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(F)CF MJYFYGVCLHNRKB-UHFFFAOYSA-N 0.000 description 1
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 1
- BKUSIKGSPSFQAC-RRKCRQDMSA-N 2'-deoxyinosine-5'-diphosphate Chemical compound O1[C@H](CO[P@@](O)(=O)OP(O)(O)=O)[C@@H](O)C[C@@H]1N1C(NC=NC2=O)=C2N=C1 BKUSIKGSPSFQAC-RRKCRQDMSA-N 0.000 description 1
- OLOQHZSCBTUIGQ-UHFFFAOYSA-L 2,2-dibutyl-1,3,2-oxathiastannolan-5-one Chemical compound CCCC[Sn]1(CCCC)OC(=O)CS1 OLOQHZSCBTUIGQ-UHFFFAOYSA-L 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical compound OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- JGBOVFKUKBGAJQ-UHFFFAOYSA-N 2-methylidenebutanediamide Chemical compound NC(=O)CC(=C)C(N)=O JGBOVFKUKBGAJQ-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 1
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-M 3-mercaptopropionate Chemical compound [O-]C(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-M 0.000 description 1
- 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 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 102100040440 Adenylate kinase isoenzyme 5 Human genes 0.000 description 1
- 101710168711 Adenylate kinase isoenzyme 5 Proteins 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
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Description
本発明は、1液組成物に関する。さらに詳しくは、セラミックス、磁器タイル、ガラス、コンクリート、窯業系成形物、プラスチック、塩ビ鋼鈑、アルマイトアルミ、電解着色アルミ、ステンレス等に用いることができる密着性、貯蔵安定性の改善された1液組成物に関する。更には、変成シリコーン用1液プライマー組成物に関する。 The present invention relates to a one-part composition. More specifically, one liquid with improved adhesion and storage stability that can be used for ceramics, porcelain tiles, glass, concrete, ceramic moldings, plastics, PVC steel plates, anodized aluminum, electrolytically colored aluminum, stainless steel, etc. Relates to the composition. Furthermore, it is related with the 1 component primer composition for modified silicone.
塗料やシーリング材分野では、各種基材との密着性を確保するために、プライマーの使用が必須となっている。
特に、窯業系成形物、コンクリートまわりに使用する場合、アルカリ性の移行により剥離が生じやすく、密着性の低下を引き起こすというような問題が残っている。これらの問題を解決する為に、本発明者らは、反応性シリル基を含有した特定の共重合体を用いることにより密着性が向上することを見出し、特許出願している(例えば、特許文献1参照)。また、作業性を考慮した1液化組成物(例えば、特許文献2参照)や二塩基酸エステルによる密着性を改良した組成物の出願を行なっている(例えば、特許文献3参照)。
また、近年、環境を中心とした溶剤排出規制が厳しくなり、PRTR法(特定化学物質の環境への排出量の把握等及び管理の改善の促進に係わる法律)によるキシレン、トルエンの規制を受け、溶剤変更や水系化を余儀なくされてきている。酢酸エステル系溶剤を重合溶剤、希釈溶剤として反応性シリル基含有共重合体を用いることができるが、1液化した場合、硬化性低下が起こり改善を行っている(例えば、引用文献4)。
In the field of paints and sealants, it is essential to use a primer in order to ensure adhesion with various substrates.
In particular, when used around ceramic moldings and concrete, there still remains a problem that peeling is likely to occur due to alkalinity transfer, causing a decrease in adhesion. In order to solve these problems, the present inventors have found that adhesion is improved by using a specific copolymer containing a reactive silyl group, and have filed a patent application (for example, patent documents). 1). In addition, applications have been filed for one-component compositions considering workability (for example, see Patent Document 2) and compositions with improved adhesion by dibasic acid esters (for example, see Patent Document 3).
In recent years, regulations on solvent emissions, especially the environment, have become stricter, and in response to regulations on xylene and toluene under the PRTR Law (Act on Understanding the Emissions of Specific Chemical Substances into the Environment and Promoting Improvements in Management) It has been forced to change the solvent and make it water-based. A reactive silyl group-containing copolymer can be used by using an acetate solvent as a polymerization solvent and a diluent solvent. However, when it is made into one solution, the curability is lowered and improved (for example, cited document 4).
しかしながら、被塗物が無機系のみならず、有機系基材など多くの種類があり、これらに対してより高い密着性が要求され、また、より汎用性の高いプライマーが求められており改善が必要である。 However, there are many types of objects to be coated, such as organic base materials as well as inorganic base materials. Higher adhesion is required for these, and more versatile primers are required. is necessary.
本発明者らは、前記のごとき実状に鑑みて鋭意研究を重ねた結果、特定の反応性シリル基含有アクリル系共重合体、硬化触媒、酢酸エステルを主成分とする溶剤からなる組成物に、特定のスズ化合物、特定のシランカップリング剤の組合せや架橋剤の併用により汎用密着性が得られることを見出した。
すなわち、本発明は
酢酸エステル系溶剤を含有とする1液組成物であって、(A)主鎖がアクリル系共重合体鎖を含有し、主鎖末端および/または側鎖に
一般式(I):
R2 a
|
−Si− (OR1)3-a (I)
(式中、 R1は水素原子または炭素数1〜10のアルキル基、R2は水素原子または炭素数1〜10のアルキル基、炭素数6〜25のアリール基および炭素数7〜12のアラルキル基から選ばれた1価の炭化水素基、aは0〜2の整数を示す)で表される炭素原子に結合した反応性シリル基を含有するアクリル系共重合体、(B)含硫黄有機錫化合物、(C)シランカップリング剤を含有することを特徴とする1液組成物に関する。
As a result of intensive studies in view of the actual situation as described above, the present inventors have obtained a composition comprising a specific reactive silyl group-containing acrylic copolymer, a curing catalyst, and a solvent mainly composed of an acetate ester, It has been found that general adhesion can be obtained by combining a specific tin compound, a specific silane coupling agent or a cross-linking agent.
That is, the present invention is a one-component composition containing an acetate solvent, wherein (A) the main chain contains an acrylic copolymer chain, and the main chain terminal and / or side chain has the general formula (I ):
R 2 a
|
-Si- (OR 1 ) 3-a (I)
Wherein R 1 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, R 2 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 25 carbon atoms, and an aralkyl having 7 to 12 carbon atoms. An acrylic copolymer containing a reactive silyl group bonded to a carbon atom represented by a monovalent hydrocarbon group selected from a group, a represents an integer of 0 to 2, and (B) a sulfur-containing organic compound The present invention relates to a one-component composition comprising a tin compound and (C) a silane coupling agent.
本発明の1液組成物は、特に、汎用密着性に貯蔵後の硬化性に優れ、折り曲げ性、無機基材に対する付着性、耐水性、耐アルカリ性等に優れるものである。 The one-component composition of the present invention is particularly excellent in general adhesion and curability after storage, and is excellent in bendability, adhesion to an inorganic substrate, water resistance, alkali resistance, and the like.
本発明の1液組成物は、湿分の存在下、室温で硬化性を有する樹脂として反応性シリル基含有単量体、その他の共重合可能な単量体からなる共重合体であるアクリル系共重合体が含有される。 The one-component composition of the present invention is an acrylic resin which is a copolymer comprising a reactive silyl group-containing monomer and other copolymerizable monomers as a resin having curability at room temperature in the presence of moisture. A copolymer is contained.
反応性シリル基含有アクリル系共重合体は、その主鎖が実質的にアクリル系単量体を共重合した主鎖からなる(以下、主鎖が実質的にアクリル系共重合鎖からなるともいう)共重合体であり、且つ、反応性シリル基が炭素原子に結合した形式で含有されているため、得られる本発明の1液組成物は各種基材、特に、無機基材に対する付着性に優れており、耐水性、耐アルカリ性などに曝しても非常に優れた密着性を有する。 The reactive silyl group-containing acrylic copolymer is composed of a main chain whose main chain is substantially copolymerized with an acrylic monomer (hereinafter, the main chain is also substantially composed of an acrylic copolymer chain). ) Since it is a copolymer and a reactive silyl group is contained in a form bonded to a carbon atom, the obtained one-component composition of the present invention has excellent adhesion to various substrates, particularly inorganic substrates. It has excellent adhesion even when exposed to water resistance and alkali resistance.
反応性シリル基含有アクリル系共重合体(A)において、一般式(I)で表される炭素原子に結合した反応性シリル基の数は、アクリル系共重合体(A)1分子あたり1個以上、好ましくは1〜15個、更に好ましくは2〜10個であることが、本発明の組成物から形成されるプライマーの接着強度、耐アルカリ性、耐久性などが優れるという点から好ましい。反応性シリル基の数が1個未満の場合は接着強度が低くなる傾向にある。 In the reactive silyl group-containing acrylic copolymer (A), the number of reactive silyl groups bonded to the carbon atom represented by the general formula (I) is one per molecule of the acrylic copolymer (A). As mentioned above, Preferably it is 1-15 pieces, More preferably, it is 2-10 pieces from the point that the adhesive strength of the primer formed from the composition of this invention, alkali resistance, durability, etc. are excellent. When the number of reactive silyl groups is less than 1, the adhesive strength tends to be low.
前記一般式(I)で表される反応性シリル基は、アクリル系共重合体(A)の主鎖の末端に結合していてもよく、側鎖に結合していてもよく、主鎖の末端および側鎖に結合していてもよい。 The reactive silyl group represented by the general formula (I) may be bonded to the end of the main chain of the acrylic copolymer (A), may be bonded to the side chain, You may couple | bond with the terminal and the side chain.
前記一般式(I)において、R1は水素原子または炭素数1〜10のアルキル基、好ましくはたとえばメチル基、エチル基、n−プロピル基、i−プロピル基、n−ブチル基、i−ブチル基などの炭素数1〜4のアルキル基である。前記アルキル基の炭素数が10を超える場合には、反応性シリル基の反応性が低下するようになる。また、前記がたとえばフェニル基、ベンジル基などのアルキル基以外の基である場合にも、反応性シリル基の反応性が低下するようになる。 In the general formula (I), R 1 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, preferably, for example, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, or an i-butyl. A C 1-4 alkyl group such as a group; When the number of carbon atoms of the alkyl group exceeds 10, the reactivity of the reactive silyl group is lowered. Also, when the above is a group other than an alkyl group such as a phenyl group and a benzyl group, the reactivity of the reactive silyl group is lowered.
また、前記一般式(I)において、R2は水素原子または炭素数1〜10のアルキル基、たとえばフェニル基などの好ましくは炭素数6〜25のアリール基およびたとえばベンジル基などの好ましくは炭素数7〜12のアラルキル基から選ばれた1価の炭化水素基である。これらの中では、本発明の組成物が硬化性に優れるという点から炭素数1〜4のアルキル基が、特には炭素数1または2が好ましい。 In the general formula (I), R 2 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, such as a phenyl group, preferably an aryl group having 6 to 25 carbon atoms, and preferably a carbon number such as a benzyl group. It is a monovalent hydrocarbon group selected from 7 to 12 aralkyl groups. In these, the C1-C4 alkyl group from the point that the composition of this invention is excellent in sclerosis | hardening, especially C1-C2 is preferable.
前記一般式(I)において、(R1O)3−aは3−aが1以上3以下になるように、すなわちaが0〜2になるように選ばれるが、アクリル系共重合体(A)の硬化性が良好になるという点からは、aが0または1の整数であることが好ましい。 In the general formula (I), (R 1 O) 3-a is selected so that 3-a is 1 or more and 3 or less, that is, a is 0 to 2, but an acrylic copolymer ( From the viewpoint that the curability of A) becomes good, it is preferable that a is an integer of 0 or 1.
一般式(I)中に存在する(R1O)3−aまたはR2aの数が2個以上の場合、2個以上含まれるR1またはR2はそれぞれ同じであってもよく、異なっていてもよい。 When the number of (R 1 O) 3-a or R 2 a present in general formula (I) is 2 or more, R 1 or R 2 contained in two or more may be the same or different. It may be.
また、アクリル系共重合体(A)としては、その分子内に一般式(I)で表される炭素原子に結合した反応性シリル基を含有する単量体単位を用いて合成したものが好ましい。なお、アクリル系共重合体(A)中の前記単量体単位(a)の含有割合は、本発明の1液組成物は硬化性、折り曲げ性、密着性、耐久性に優れるという点から、重合成分全量の1〜30重量%、さらには2〜20重量%、とくには2〜15重量%であるのが好ましい。 Moreover, as an acrylic copolymer (A), what was synthesize | combined using the monomer unit containing the reactive silyl group couple | bonded with the carbon atom represented by general formula (I) in the molecule | numerator is preferable. . The content ratio of the monomer unit (a) in the acrylic copolymer (A) is that the one-component composition of the present invention is excellent in curability, bendability, adhesion, and durability. It is preferably 1 to 30% by weight, more preferably 2 to 20% by weight, particularly 2 to 15% by weight of the total amount of the polymerization components.
使用量が1重量%未満の場合には、硬化性が不充分となる傾向にあり、30重量%をこえる場合には、保存安定性が低下する傾向にある。 When the amount used is less than 1% by weight, the curability tends to be insufficient, and when it exceeds 30% by weight, the storage stability tends to decrease.
前記反応性シリル基含有アクリル系共重合体の数平均分子量は、密着性、耐久性などの物性が優れるという点から、2000以上、さらには6000以上、50000以下更には25000以下であることが好ましい。
前記アクリル系共重合体のガラス転移温度は、指触乾燥性、ほこり付着性などの物性が優れるという点から、35℃以上であることが好ましい。35℃未満では低温時の乾燥性が悪くなり、また、付着性も低下する傾向があり好ましくない。
The number average molecular weight of the reactive silyl group-containing acrylic copolymer is preferably 2000 or more, more preferably 6000 or more, 50000 or less, and further 25000 or less from the viewpoint of excellent physical properties such as adhesion and durability. .
The glass transition temperature of the acrylic copolymer is preferably 35 ° C. or higher from the viewpoint of excellent physical properties such as dryness to the touch and dust adhesion. If it is less than 35 degreeC, the drying property at the time of low temperature worsens and there exists a tendency for adhesiveness to fall, and it is not preferable.
前記のごときアクリル系共重合体は、単独で用いてもよく、2種以上併用してもよい。 The acrylic copolymers as described above may be used alone or in combination of two or more.
つぎに、アクリル系共重合体の製法の一例について説明する。 Next, an example of a method for producing an acrylic copolymer will be described.
アクリル系共重合体は、たとえば重合性2重結合および炭素原子に結合した反応性シリル基を含有する単量体、(メタ)アクリル酸および/またはその誘導体ならびに必要により用いられるその他の単量体を含有するものを重合することによって製造することができる。
前記単量体の具体例としては、たとえば
Acrylic copolymers include, for example, monomers containing a polymerizable double bond and a reactive silyl group bonded to a carbon atom, (meth) acrylic acid and / or derivatives thereof, and other monomers used as necessary It can manufacture by polymerizing what contains.
Specific examples of the monomer include, for example,
などの下記一般式(II):
R3 R2a
| |
CH2=C−Si−(OR1)3-a
(式中、R1、R2、aは前記と同じ、 R3は水素原子またはメチル基を示す)で表される化合物;
The following general formula (II):
R 3 R 2 a
| |
CH 2 = C-Si- (OR 1) 3-a
(Wherein R 1 , R 2 and a are the same as above, R 3 represents a hydrogen atom or a methyl group);
などの下記一般式(III):
R3 R2 a
| |
CH2=C−COO(CH2)n−Si−(OR1)3-a
(式中、R1、R2、R3およびaは前記と同じ、nは1〜12の整数を示す。)で表される化合物;
CH2=CH−CH2OCO(o-C6H4)COO(CH2)3Si(OCH3)3
CH2=CH−CH2OCO(o-C6H4)COO(CH2)3Si(CH3)(OCH3)2
などの下記一般式(IV):
The following general formula (III):
R 3 R 2 a
| |
CH 2 = C-COO (CH 2) n -Si- (OR 1) 3-a
(Wherein R 1 , R 2 , R 3 and a are the same as described above, n represents an integer of 1 to 12);
CH 2 = CH-CH 2 OCO (o-C 6 H 4) COO (CH 2) 3 Si (OCH 3) 3
CH 2 = CH-CH 2 OCO (o-C 6 H 4) COO (CH 2) 3 Si (CH 3) (OCH 3) 2
The following general formula (IV):
(式中、R1、 R2、 R3、aおよびnは前記と同じ)で表される化合物: (Wherein R 1 , R 2 , R 3 , a and n are as defined above):
などの一般式(V): General formula (V):
(式中、R1, R2, R3,aは前記と同じ、mは1〜14の整数を示す。)で表される化合物; (Wherein R 1 , R 2 , R 3 and a are the same as described above, m represents an integer of 1 to 14);
(式中、pは0〜20の整数を示す。)などの下記一般式(VI): (Wherein p represents an integer of 0 to 20) and the following general formula (VI):
等が例示できる。 Etc. can be illustrated.
本発明においては、前記、炭素数10以上のアルキル基を有する(メタ)アクリル酸アルキルエステル単量体(b)を用いるのが塗膜の内部応力が緩和されるので好ましい。具体例としてはラウリル(メタ)アクリレート、トリデシル(メタ)アクリレート、セチル(メタ)アクリレート、ステアリル(メタ)アクリレート、ドコサニル(メタ)アクリレート、ベヘニル(メタ)アクリレート等が挙げられる。 In the present invention, it is preferable to use the (meth) acrylic acid alkyl ester monomer (b) having an alkyl group having 10 or more carbon atoms because the internal stress of the coating film is relieved. Specific examples include lauryl (meth) acrylate, tridecyl (meth) acrylate, cetyl (meth) acrylate, stearyl (meth) acrylate, docosanyl (meth) acrylate, and behenyl (meth) acrylate.
前記、単量体(b)の使用量は、通常用いる重合成分全量の5〜30重量%、さらには10〜25重量%、とくには10〜20重量%であるのが好ましい。使用量が5重量%未満の場合は塗膜の内部応力の硬化が小さく、又、30重量%を超える場合は相溶性が低下するので好ましくない。 The amount of the monomer (b) used is preferably 5 to 30% by weight, more preferably 10 to 25% by weight, and particularly preferably 10 to 20% by weight, based on the total amount of the polymerization components to be usually used. When the amount used is less than 5% by weight, curing of the internal stress of the coating film is small, and when it exceeds 30% by weight, the compatibility is lowered, which is not preferable.
前記、その他の共重合可能な単量体(c)の具体例としては、たとえばメチル(メタ)アクリレート、エチル(メタ)アクリレート、ブチル(メタ)アクリレート、2ーエチルヘキシル(メタ)アクリレート、ベンジル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、トリフルオロエチル(メタ)アクリレート、ペンタフルオロプロピル(メタ)アクリレート、パーフルオロシクロヘキシル(メタ)アクリレート、(メタ)アクリロニトリル、グリシジル(メタ)アクリレート、ジメチルアミノエチル(メタ)アクリレート、ジエチルアミノエチル(メタ)アクリレート、(メタ)アクリルアミド、α−エチル(メタ)アクリルアミド、N−ブトキシメチル(メタ)アクリルアミド、N,N−ジメチル(メタ)アクリルアミド、N−メチル(メタ)アクリルアミド(メタ)アクリロイルモルホリン、2−ヒドロキシエチル(メタ)アクリレート、2ーヒドロキシプロピル(メタ)アクリレート、N−メチロール(メタ)アクリルアミド、アロニクスM−5700、マクロモノマーであるAS−6、AN−6、AA−6、AB−6、AK−5などの化合物(以上、東亜合成化学工業(株)製)、Placcel FA−1、Placcel FA−4、Placcel FM−1、Placcel FM−4(以上、ダイセル化学工業(株)製)、(メタ)アクリル酸のヒドロキシアルキルエステル類とリン酸またはリン酸エステル類との縮合生成物などのリン酸エステル基含有(メタ)アクリル系化合物、ウレタン結合やシロキサン結合を含む(メタ)アクリレートなどが挙げられる。 Specific examples of the other copolymerizable monomer (c) include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, benzyl (meth) ) Acrylate, cyclohexyl (meth) acrylate, trifluoroethyl (meth) acrylate, pentafluoropropyl (meth) acrylate, perfluorocyclohexyl (meth) acrylate, (meth) acrylonitrile, glycidyl (meth) acrylate, dimethylaminoethyl (meth) Acrylate, diethylaminoethyl (meth) acrylate, (meth) acrylamide, α-ethyl (meth) acrylamide, N-butoxymethyl (meth) acrylamide, N, N-dimethyl (meth) acrylamide N-methyl (meth) acrylamide (meth) acryloylmorpholine, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, N-methylol (meth) acrylamide, Aronics M-5700, AS-macromonomer 6, compounds such as AN-6, AA-6, AB-6, AK-5 (above, manufactured by Toa Synthetic Chemical Industry Co., Ltd.), Placcel FA-1, Placcel FA-4, Placcel FM-1, Placcel FM -4 (manufactured by Daicel Chemical Industries, Ltd.), phosphate ester group-containing (meth) acrylic compounds such as condensation products of hydroxyalkyl esters of (meth) acrylic acid and phosphoric acid or phosphate esters , (Meth) acrylates containing urethane bonds and siloxane bonds, etc. And the like.
これらの単量体(c)は単独で用いてもよく、2種以上併用してもよい。 These monomers (c) may be used alone or in combination of two or more.
前記単量体(c)の使用量は、通常用いる重合成分全量の5〜95重量%、さらには30〜90重量%、とくには40〜85重量%であるのが好ましい。 The amount of the monomer (c) used is preferably 5 to 95% by weight, more preferably 30 to 90% by weight, and particularly preferably 40 to 85% by weight based on the total amount of the polymerization components to be used.
また、本発明においては、得られる本発明の組成物から形成されるプライマーの密着性をさらに向上させる目的で、たとえば主鎖にウレタン結合やシロキサン結合により形成されたセグメントを、50重量%を超えない範囲でアクリル系共重合体の製造時に導入してもよい。 In the present invention, for the purpose of further improving the adhesion of the primer formed from the composition of the present invention obtained, for example, the segment formed by urethane bond or siloxane bond in the main chain exceeds 50% by weight. It may be introduced at the time of production of the acrylic copolymer as long as it is not.
前記単量体以外の単量体の具体例としては、たとえばスチレン、αーメチルスチレン、クロロスチレン、スチレンスルホン酸、4ーヒドロキシスチレン、ビニルトルエンなどの芳香族炭化水素系ビニル化合物;マレイン酸、フマル酸、イタコン酸、(メタ)アクリル酸などの不飽和カルボン酸、これらのアルカリ金属塩、アンモニウム塩、アミン塩などの塩;無水マレイン酸などの不飽和カルボン酸の酸無水物、これら酸無水物と炭素数1〜20の直鎖状または分岐鎖を有するアルコールまたはアミンとのジエステルまたはハーフエステルなどの不飽和カルボン酸のエステル;酢酸ビニル、プロピオン酸ビニル、ジアリルフタレートなどのビニルエステルやアリル化合物;ビニルピリジン、アミノエチルビニルエーテルなどのアミノ基含有ビニル系化合物;イタコン酸ジアミド、クロトン酸アミド、マレイン酸ジアミド、フマル酸ジアミド、N−ビニルピロリドンなどのアミド基含有ビニル系化合物;2ーヒドロキシエチルビニルエーテル、メチルビニルエーテル、シクロヘキシルビニルエーテル、塩化ビニル、塩化ビニリデン、クロロプレン、プロピレン、ブタジエン、イソプレン、フルオロオレフィンマレイミド、N−ビニルイミダゾール、ビニルスルホン酸などのその他ビニル系化合物などが挙げられる。これらは単独で用いてもよく、2種以上併用してもよい。 Specific examples of monomers other than the above monomers include aromatic hydrocarbon vinyl compounds such as styrene, α-methylstyrene, chlorostyrene, styrenesulfonic acid, 4-hydroxystyrene, vinyltoluene; maleic acid, fumaric acid , Unsaturated carboxylic acids such as itaconic acid and (meth) acrylic acid, salts thereof such as alkali metal salts, ammonium salts and amine salts; acid anhydrides of unsaturated carboxylic acids such as maleic anhydride, and these acid anhydrides Esters of unsaturated carboxylic acids such as diesters or half esters with linear or branched alcohols or amines having 1 to 20 carbon atoms; vinyl esters or allyl compounds such as vinyl acetate, vinyl propionate, diallyl phthalate; vinyl Amino group-containing vinyl such as pyridine and aminoethyl vinyl ether Amide group compounds: Itaconic acid diamide, crotonic acid amide, maleic acid diamide, fumaric acid diamide, amide group-containing vinyl compounds such as N-vinylpyrrolidone; 2-hydroxyethyl vinyl ether, methyl vinyl ether, cyclohexyl vinyl ether, vinyl chloride, vinylidene chloride , Other vinyl compounds such as chloroprene, propylene, butadiene, isoprene, fluoroolefin maleimide, N-vinylimidazole, and vinyl sulfonic acid. These may be used alone or in combination of two or more.
前記アクリル系共重合体は、たとえば特開昭54−36395号公報、特開昭57−55954号公報などに記載のヒドロシリル化法または反応性シリル基を含有する単量体を用いた溶液重合法によって製造することができるが、合成の容易さなどの点から反応性シリル基を含有する単量体を用い、2,2’−アゾ ビス(2−メチルブチロニトリル)などのアゾ系ラジカル重合開始剤を用いた溶液重合法によって製造することがとくに好ましい。 Examples of the acrylic copolymer include a hydrosilylation method or a solution polymerization method using a monomer containing a reactive silyl group described in JP-A-54-36395 and JP-A-57-55954. Azo radical polymerization such as 2,2'-azobis (2-methylbutyronitrile) using a monomer containing a reactive silyl group from the viewpoint of ease of synthesis. It is particularly preferable to produce by a solution polymerization method using an initiator.
前記溶液重合法に用いられる溶剤は、酢酸エチル、酢酸ブチルなどの酢酸エステル系溶剤を主成分とするものであるが、その他、非水系のものであれば併用にはとくに制限はない。中でもメタノール、イソプロピルアルコール、nーブタノール、イソブタノール、ヘキサノール、オクタノールなどのアルコール類が好ましいが、nーヘキサン、シクロヘキサンなどの脂肪族炭化水素類;エチルセロソルブ、ブチルセロソロブなどのセロソルブ類;セロソルブアセテートなどのエーテルエステル類;メチルエチルケトン、アセト酢酸エチル、アセチルアセトン、メチルイソブチルケトン、アセトンなどのケトン類なども使用できる。酢酸エステル系溶剤を主成分とするとは、溶剤として酢酸エステル系溶剤が本願組成部の全溶剤中50重量%以上、好ましくは65重量%以上、さらに好ましくは80重量%以上特には95重量%以上である。本願の酢酸エステル系溶剤は本願組成物中に主成分として存在すればよく、(A)成分の共重合体の合成前、中、後、あるいはその他の時期のいずれに加えてもよい。 The solvent used in the solution polymerization method is mainly composed of an acetate solvent such as ethyl acetate or butyl acetate, but there are no particular restrictions on the combination as long as it is a non-aqueous solvent. Of these, alcohols such as methanol, isopropyl alcohol, n-butanol, isobutanol, hexanol and octanol are preferable, but aliphatic hydrocarbons such as n-hexane and cyclohexane; cellosolves such as ethyl cellosolve and butyl cellosorb; ether esters such as cellosolve acetate Ketones such as methyl ethyl ketone, ethyl acetoacetate, acetylacetone, methylisobutylketone, and acetone can also be used. An acetic acid ester solvent as a main component means that the acetic acid ester solvent as a solvent is 50% by weight or more, preferably 65% by weight or more, more preferably 80% by weight or more, particularly 95% by weight or more in the total solvent of the composition part of the present application. It is. The acetate ester-based solvent of the present application may be present as a main component in the composition of the present application, and may be added before, during, or after the synthesis of the copolymer of component (A).
また、前記溶液重合の際には、必要に応じて、たとえばn−ドデシルメルカプタン、t−ドデシルメルカプタン、n−ブチルメルカプタン、γーメルカプトプロピルトリメトキシシラン、γーメルカプトプロピルトリエトキシシラン、(CH3O)3Si−S−S−Si(OCH3)3,(CH3O)3Si−S8−Si(OCH3)3などの連鎖移動剤を単独または2種以上併用することにより、得られるアクリル系共重合体(A)の分子量を調整してもよい。とくに、たとえばγーメルカプトプロピルトリメトキシシランなどのアルコキシシリル基を分子中に有する連鎖移動剤を用いた場合には、アクリル系共重合体の末端に反応性シリル基を導入することができる。かかる連鎖移動剤の使用量は、用いる重合成分全量の0.05〜10%、更には0.1〜8%であることが好ましい。 In the solution polymerization, if necessary, for example, n-dodecyl mercaptan, t-dodecyl mercaptan, n-butyl mercaptan, γ-mercaptopropyltrimethoxysilane, γ-mercaptopropyltriethoxysilane, (CH 3 O) 3 Si—S—S—Si (OCH 3 ) 3 , (CH 3 O) 3 Si—S 8 —Si (OCH 3 ) 3 or other chain transfer agents are used alone or in combination of two or more. The molecular weight of the acrylic copolymer (A) to be produced may be adjusted. In particular, when a chain transfer agent having an alkoxysilyl group in the molecule, such as γ-mercaptopropyltrimethoxysilane, is used, a reactive silyl group can be introduced at the end of the acrylic copolymer. The amount of the chain transfer agent used is preferably 0.05 to 10%, more preferably 0.1 to 8% of the total amount of polymerization components used.
前記(A)成分には、さらに、(E)脱水剤やアルコールを配合することにより貯蔵安定性を向上させることができる。 Storage stability can be improved by further blending (E) a dehydrating agent or alcohol with the component (A).
前記脱水剤の具体例としては、たとえば、オルトギ酸メチル、オルトギ酸エチル、オルト酢酸メチル、オルト酢酸エチル、オルトプロピオン酸トリメチル、オルトプロピオン酸トリエチル、オルトイソプロピオン酸トリメチル、オルトイソプロピオン酸トリエチル、オルト酪酸トリメチル、オルト酪酸トリエチル、オルトイソ酪酸トリメチル、オルトイソ酪酸トリエチルなどの加水分解性エステル化合物などが挙げられる。これらの中では脱水効果の点でオルト酢酸メチルが好ましい。これらは単独で用いてもよく2種以上併用してもよい。上記において酢酸エステル系溶剤は、本願発明の酢酸エステル系溶剤として用いられ、反応性シリル基含有アクリル系共重合体の合成前から、あるいは合成中あるいは合成後用いて酢酸エステル系溶剤を主成分としてもよい。 Specific examples of the dehydrating agent include, for example, methyl orthoformate, ethyl orthoformate, methyl orthoacetate, ethyl orthoacetate, trimethyl orthopropionate, triethyl orthopropionate, trimethyl orthoisopropionate, triethyl orthoisopropionate, ortho Examples include hydrolysable ester compounds such as trimethyl butyrate, triethyl orthobutyrate, trimethyl orthoisobutyrate, triethyl orthoisobutyrate, and the like. Among these, methyl orthoacetate is preferable from the viewpoint of dehydration effect. These may be used alone or in combination of two or more. In the above, the acetate solvent is used as the acetate solvent of the present invention, and is used before, during or after the synthesis of the reactive silyl group-containing acrylic copolymer as the main component. Also good.
また、前記アルキルアルコールの具体例としては、例えばメタノール、エタノールなどの炭素数1から4の低級アルコールなどが挙げられる。 Specific examples of the alkyl alcohol include lower alcohols having 1 to 4 carbon atoms such as methanol and ethanol.
前記脱水剤やアルキルアルコールは、たとえばアクリル系共重合体(A)を重合する前の成分に加えてもよく、アクリル系共重合体(A)の重合中に加えてもよく、また、得られたアクリル系共重合体(A)とそのほかの成分との混合時に加えてもよく特に制限はない。 The dehydrating agent and alkyl alcohol may be added, for example, to the component before the acrylic copolymer (A) is polymerized, or may be added during the polymerization of the acrylic copolymer (A), and may be obtained. The acrylic copolymer (A) and other components may be added at the time of mixing with no particular limitation.
前記脱水剤の配合量には特に限定はないが、通常アクリル系共重合体(A)100重量部に対して脱水剤が0.5〜20重量部程度、更には2〜10重量部程度であるのが好ましい。 The amount of the dehydrating agent is not particularly limited, but the dehydrating agent is usually about 0.5 to 20 parts by weight, more preferably about 2 to 10 parts by weight with respect to 100 parts by weight of the acrylic copolymer (A). Preferably there is.
本発明の(B)成分である含硫黄有機錫化合物としては、ジブチル錫チオグリコレート、ジブチル錫ビスイソノニル3−メルカプトプロピオネート、ジブチル錫ビスイソオクチルチオグリコレート、ジブチル錫ビス2−エチルヘキシルチオグリコレート、ジメチル錫ビスドデシルメルカプチド、ジブチル錫ビスドデシルメルカプチド、ジオクチル錫ビスドデシルメルカプチド、ジメチル錫ビス(オクチルチオグルコール酸エステル)塩などが挙げられる。 Examples of the sulfur-containing organotin compound which is the component (B) of the present invention include dibutyltin thioglycolate, dibutyltin bisisononyl 3-mercaptopropionate, dibutyltin bisisooctylthioglycolate, dibutyltin bis2-ethylhexylthioglycolate. And dimethyltin bisdodecyl mercaptide, dibutyltin bisdodecyl mercaptide, dioctyltin bisdodecyl mercaptide, dimethyltin bis (octylthioglycolate) salt and the like.
なかでも、貯蔵安定性およびポットライフ後の密着性が良好な点から、ジブチル錫ビスドデシルメルカプチド、ジオクチル錫ビスドデシルメルカプチドなどが好ましい。 Of these, dibutyltin bisdodecyl mercaptide, dioctyltin bisdodecyl mercaptide and the like are preferable from the viewpoint of good storage stability and adhesion after pot life.
また、(R4)(R5)Sn(S−R6)(S−R7)で表される有機錫化合物が用いられる(式中R4、R5は同じかまたは異なり炭素数が1〜8の直鎖あるいは分岐したアルキル基、R6、R7は直鎖あるいは分岐した炭素数1〜20のアルキル基である)。
これらの(B)成分はアクリル共重合体(A)100重量部に対して0.05〜20重量部、更には0.1〜10重量部が好ましい。本発明においては使用量が0.05重量部未満の場合は硬化性が低下する傾向にあり、20重量部を超える場合は耐水性や貯蔵安定性が低下する傾向にある。
In addition, an organic tin compound represented by (R 4 ) (R 5 ) Sn (S—R 6 ) (S—R 7 ) is used (wherein R 4 and R 5 are the same or different and have 1 carbon number). -8 linear or branched alkyl groups, R 6 and R 7 are linear or branched alkyl groups having 1 to 20 carbon atoms).
These components (B) are preferably 0.05 to 20 parts by weight, more preferably 0.1 to 10 parts by weight, based on 100 parts by weight of the acrylic copolymer (A). In the present invention, when the amount used is less than 0.05 parts by weight, the curability tends to decrease, and when it exceeds 20 parts by weight, the water resistance and storage stability tend to decrease.
(C)成分のシランカップリング剤としては、アミノシラン化合物、エポキシシラン化合物、メルカプトシラン化合物が挙げられる。 (C) As a silane coupling agent of a component, an aminosilane compound, an epoxysilane compound, and a mercaptosilane compound are mentioned.
アミノシラン化合物としては、γ−アミノプロピルトリエトキシシラン、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−アミノプロピルトリエトキシシラン、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、γ−フェニルアミノプロピルトリメトキシシラン、ビス(トリメトキシシリルプロピル)アミン、ビス(トリエトキシシリルプロピル)アミンなどが挙げられる。 Examples of aminosilane compounds include γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N- (β-aminoethyl) -γ-aminopropyltrimethoxysilane, N- (β-aminoethyl) -γ-amino. Propyltriethoxysilane, N- (β-aminoethyl) -γ-aminopropylmethyldimethoxysilane, γ-phenylaminopropyltrimethoxysilane, bis (trimethoxysilylpropyl) amine, bis (triethoxysilylpropyl) amine, etc. Can be mentioned.
エポキシシラン化合物としてはγ−グリシドキシプリピルメチルジメトキシシラン、γ−グリシドキシプリピルメチルジエトキシシラン、γ−グリシドキシプリピルトリメトキシシラン、β−(3,4−エポキシシクロヘキシ)エチルトリメトキシシランが挙げられる。 Epoxy silane compounds include γ-glycidoxypropylmethyldimethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, γ-glycidoxypropyltrimethoxysilane, β- (3,4-epoxycyclohexyl) Ethyltrimethoxysilane is mentioned.
メルカプトシラン化合物としてはγ−メルカプトプリピルトリメトキシシラン、γ−メルカプトプリピルトリエトキシシラン、γ−メルカプトプリピルメチルジメトキシシランが挙げられる。 Examples of the mercaptosilane compound include γ-mercaptopropyl trimethoxysilane, γ-mercaptopropyl triethoxysilane, and γ-mercaptopropylmethyldimethoxysilane.
特に、各種基材に対する密着性を向上できる点から、ビス(トリメトキシシリルプロピル)アミン、ビス(トリエトキシシリルプロピル)アミン、γ−アミノプロピルトリメトキシシランとγ−イソシアネートプロピルトリメトキシシランの反応物、γ−アミノプロピルトリメトキシシランとγ−グリシドキシプロピルトリメトキシシランの反応物、エポキシ樹脂とγ−アミノプロピルトリエトキシシランの反応物、γ−グリシドキシプロピルトリメトキシシランが好ましい。 In particular, the reaction product of bis (trimethoxysilylpropyl) amine, bis (triethoxysilylpropyl) amine, γ-aminopropyltrimethoxysilane and γ-isocyanatopropyltrimethoxysilane because it can improve adhesion to various substrates. The reaction product of γ-aminopropyltrimethoxysilane and γ-glycidoxypropyltrimethoxysilane, the reaction product of epoxy resin and γ-aminopropyltriethoxysilane, and γ-glycidoxypropyltrimethoxysilane are preferred.
シランカップリング剤の使用量は、本発明においては(A)成分100重量部に対して0.1〜50重量部、更には0.1〜30重量部、特には0.5〜20重量部の範囲が好ましい。使用量が0.1部より少なくなると付着性の向上が不十分となり、50重量部を超えると相溶性が低下する恐れがある。 In the present invention, the amount of the silane coupling agent used is 0.1 to 50 parts by weight, more preferably 0.1 to 30 parts by weight, particularly 0.5 to 20 parts by weight per 100 parts by weight of component (A) The range of is preferable. When the amount used is less than 0.1 part, the adhesion is not sufficiently improved, and when it exceeds 50 parts by weight, the compatibility may be lowered.
本発明の(D)成分である二塩基酸ジアルキルエステルとしてはマロン酸ジメチル、コハク酸ジメチル、マレイン酸ジメチル、グルタール酸ジメチル、アジピン酸ジメチル、アジピン酸ジブチル、マロン酸ジエチル、コハク酸ジエチル等が挙げられる。これらの二塩基酸ジアルキルエステルはアクリル共重合体(A)100重量部に対して0.5〜100重量部、更には2〜50重量部、特には5〜30重量部が好ましい。本発明においては0.5重量部未満では、貯蔵後の硬化性改善効果や折り曲げ性改善効果が小さく、又、100重量部以上では硬度、耐候性が低下する傾向にある。 Examples of the dibasic acid dialkyl ester as component (D) of the present invention include dimethyl malonate, dimethyl succinate, dimethyl maleate, dimethyl glutarate, dimethyl adipate, dibutyl adipate, diethyl malonate, diethyl succinate and the like. It is done. These dibasic acid dialkyl esters are preferably 0.5 to 100 parts by weight, more preferably 2 to 50 parts by weight, and particularly preferably 5 to 30 parts by weight with respect to 100 parts by weight of the acrylic copolymer (A). In the present invention, if it is less than 0.5 parts by weight, the effect of improving curability and the effect of improving bendability after storage is small, and if it is 100 parts by weight or more, the hardness and weather resistance tend to decrease.
本発明の(F)成分である脱水促進剤としては塩酸、硫酸、リン酸、硝酸などの無機酸、蟻酸、酢酸、安息香酸などの有機酸などが挙げられる。これらの脱水促進剤は(E)成分100重量部に対して0.0001〜1重量部、更には0.001〜0.1重量部が好ましい。 Examples of the dehydration accelerator as the component (F) of the present invention include inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid and nitric acid, and organic acids such as formic acid, acetic acid and benzoic acid. These dehydration accelerators are preferably 0.0001 to 1 part by weight, more preferably 0.001 to 0.1 part by weight, per 100 parts by weight of component (E).
本発明の1液組成物は、上記(A)成分であるアクリル系重合体、(D)成分である二塩基酸ジアルキルエステル、希釈溶剤を加え、予め脱水剤、必要に応じて(F)脱水促進剤を用いて脱水した後に、(B)成分である含硫黄有機錫化合物、(C)成分であるシランカップリング剤を配合することが貯蔵安定性の点より好ましい。 In the one-component composition of the present invention, an acrylic polymer as the component (A), a dibasic acid dialkyl ester as the component (D) and a diluting solvent are added, and a dehydrating agent is added in advance. After dehydration using an accelerator, it is preferable from the viewpoint of storage stability that a sulfur-containing organotin compound as the component (B) and a silane coupling agent as the component (C) are blended.
本発明の1液組成物は被着体に直接塗布したり、又、旧塗膜上や劣化したシーリング剤の打ち継ぎ用として塗布することも可能である。1液組成物を塗布した後、その上に弾性シーリング材を打つこともでき、塗料を塗装することも可能である。1液組成物の塗布方法及び該硬化性組成物の塗布方法としては、特に限定はなく、従来公知の塗布手段、例えばハケによる塗布、ロールによる塗布、スプレーによる塗布等を広く採用する事ができる。塗布量としては、被着体の1m2面積に相当する部分あたり、通常20〜400g程度、好ましくは40〜100g程度とするのが良い。被着体上に塗膜を形成させるには、塗布後、これを室温にて乾燥しても良いし、又は、50〜120℃程度の温度で加熱しても良い。 The one-component composition of the present invention can be applied directly to an adherend, or can be applied on an old coating film or as a joint for a deteriorated sealing agent. After applying the one-component composition, an elastic sealant can be applied thereon, and a paint can be applied. The coating method of the one-component composition and the coating method of the curable composition are not particularly limited, and conventionally known coating means such as brush coating, roll coating, spray coating, etc. can be widely used. . The coating amount is usually about 20 to 400 g, preferably about 40 to 100 g per portion corresponding to 1 m 2 area of the adherend. In order to form a coating film on an adherend, it may be dried at room temperature after coating, or may be heated at a temperature of about 50 to 120 ° C.
また、本発明の1液組成物には、たとえば酸化チタン、群青、紺青、亜鉛華、ベンガラ、黄鉛、鉛白、カーボンブラック、透明酸化鉄、硫酸バリウム、タルク、雲母、炭酸カルシウム、アルミニウム粉などの無機顔料や体質顔料、アゾ系顔料、トリフェニルメタン系顔料、キノリン系顔料、アントラキノン系顔料、フタロシアニン系顔料などの有機顔料などの顔料;希釈剤、紫外線吸収剤、光安定剤、タレ防止剤、レベリング剤などの添加剤;ニトロセルロース、セルロースアセテートブチレートなどの繊維素;エポキシ樹脂、メラミン樹脂、塩化ビニル樹脂、ウレタン樹脂、フッ素樹脂、塩素化ポリプロピレン、塩化ゴム、ポリビニルブチラール、ポリシロキサンなどの樹脂などを適宜加えてもよい。 The one-component composition of the present invention includes, for example, titanium oxide, ultramarine blue, bitumen, zinc white, bengara, yellow lead, white lead, carbon black, transparent iron oxide, barium sulfate, talc, mica, calcium carbonate, aluminum powder. Pigments such as inorganic pigments such as inorganic pigments, extender pigments, azo pigments, triphenylmethane pigments, quinoline pigments, anthraquinone pigments, phthalocyanine pigments; diluents, UV absorbers, light stabilizers, sagging prevention Additives such as additives and leveling agents; Fibrin such as nitrocellulose and cellulose acetate butyrate; Epoxy resin, melamine resin, vinyl chloride resin, urethane resin, fluororesin, chlorinated polypropylene, chlorinated rubber, polyvinyl butyral, polysiloxane, etc. These resins may be added as appropriate.
次に、本発明の塗料用硬化性樹脂組成物を実施例に基づいてさらに詳細に説明するが、本発明はかかる実施例のみに限定されるものではない。 Next, although the curable resin composition for coating materials of this invention is demonstrated in detail based on an Example, this invention is not limited only to this Example.
製造例1(アクリル系共重合体(A−1)の製造)
撹拌機、温度計、還流冷却器、窒素ガス導入管および滴下ロートを備えた反応容器に酢酸ブチル50重量部を仕込み、窒素ガスを導入しつつ110℃に昇温した。そののち、γ−メタクリロキシプロピルトリメトキシシラン6.6重量部、ステアリルメタクリレート14重量部、メチルメタクリレート73重量部、n−ブチルアクリレート5.4重量部、アクリルアミド1重量部、酢酸ブチル18重量部および2,2’−アゾビス(2−メチルブチロニトリル)0.8重量部からなる混合物を滴下ロートにより5時間かけて等速滴下した。
Production Example 1 (Production of acrylic copolymer (A-1))
A reaction vessel equipped with a stirrer, thermometer, reflux condenser, nitrogen gas inlet tube and dropping funnel was charged with 50 parts by weight of butyl acetate and heated to 110 ° C. while introducing nitrogen gas. Thereafter, 6.6 parts by weight of γ-methacryloxypropyltrimethoxysilane, 14 parts by weight of stearyl methacrylate, 73 parts by weight of methyl methacrylate, 5.4 parts by weight of n-butyl acrylate, 1 part by weight of acrylamide, 18 parts by weight of butyl acetate and A mixture consisting of 0.8 parts by weight of 2,2′-azobis (2-methylbutyronitrile) was dropped at a constant rate with a dropping funnel over 5 hours.
滴下終了後、2,2’−アゾ ビス(2−メチルブチロニトリル)0.1重量部、酢酸ブチル5重量部および酢酸ブチル8重量部を1時間かけて等速滴下したのち、110℃で2時間熟成してから冷却し、樹脂溶液に酢酸ブチルを加えて樹脂固形分濃度が40%のアクリル系共重合体(A−1)を得た。
得られたアクリル系共重合体(A−1)の数平均分子量は16000であった。
又、計算上のガラス転移温度は52℃であった。
After completion of the dropwise addition, 0.1 part by weight of 2,2′-azobis (2-methylbutyronitrile), 5 parts by weight of butyl acetate and 8 parts by weight of butyl acetate were dropped at a constant rate over 1 hour, and then at 110 ° C. After aging for 2 hours, the mixture was cooled and butyl acetate was added to the resin solution to obtain an acrylic copolymer (A-1) having a resin solid content concentration of 40%.
The number average molecular weight of the obtained acrylic copolymer (A-1) was 16000.
The calculated glass transition temperature was 52 ° C.
製造例2(弾性シーリング材の製造)
1分子当たり平均2.1個のメチルジメトキシシリル基[−Si(CH3)(OCH3)2]を有する数平均分子量17,000のプロピレンオキシド重合体100重量部、可塑剤としてDIDP(ジイソデシルフタレート)55重量部、フィラーとして表面処理膠質炭酸カルシウム100重量部、酸化チタン20重量部、タレ防止剤として脂肪族アマイドワックス2重量部、紫外線吸収剤としてチヌビン327(チバガイギー社製)1重量部、光安定剤としてチヌビン770(チバガイギー社製)1重量部、脱水剤としてビニルトリメトキシシラン2重量部、密着改良剤としてA1120(アミノシラン、日本ユニカー社製)、硬化触媒としてU−220(日東化成社製)2重量部を加え、2軸プラネタリーミキサーを用い硬化性組成物を得た。
Production Example 2 (Production of elastic sealing material)
100 parts by weight of a propylene oxide polymer having a number average molecular weight of 17,000 having an average of 2.1 methyldimethoxysilyl groups [—Si (CH 3 ) (OCH 3 ) 2 ] per molecule, and DIDP (diisodecyl phthalate) as a plasticizer ) 55 parts by weight, 100 parts by weight of surface-treated colloidal calcium carbonate as filler, 20 parts by weight of titanium oxide, 2 parts by weight of aliphatic amide wax as sagging inhibitor, 1 part by weight of tinuvin 327 (manufactured by Ciba Geigy) as an ultraviolet absorber, light Tinuvin 770 (manufactured by Ciba Geigy) as a stabilizer, 2 parts by weight of vinyltrimethoxysilane as a dehydrating agent, A1120 (aminosilane, manufactured by Nihon Unicar) as an adhesion improver, and U-220 (manufactured by Nitto Kasei) as a curing catalyst ) Add 2 parts by weight and use a biaxial planetary mixer for curable composition It was obtained.
参考例1および2、実施例3〜6、参考例7、比較例1〜3
製造例1で得られたアクリル系共重合体(A)の樹脂固形分100重量部に対して、表1に示す各種添加剤を配合して1液組成物を得た。
B−1:ジブチル錫ビスイソオクチルチオグリコレート
B−2:ジブチル錫ビスドデシルメルカプタイド
B−3:スズオキサイドとエチルシリケートの反応物
C−1:エピコート828(ジャパンエポキシレジン社製)とA1100(モメンティブ社製)の1対1(モル比)反応物
C−2:ビス(トリエトキシシリルプロピル)アミン
C−3:ビス(トリメトキシシリルプロピル)アミン
C−4:γ−グリシドキシプロピルトリメトキシシラン
C−5:γ−メルカプトプロピルトリメトキシシラン
D−1:アジピン酸ジメチルエステル
E−1:オルソ酢酸エステル
F−1:濃塩酸の1%メタノール溶液
その他の成分:アデカレジンEP−4100(アデカ社製)
Reference Examples 1 and 2, Examples 3 to 6, Reference Example 7, Comparative Examples 1 to 3
Various additives shown in Table 1 were blended with 100 parts by weight of the resin solid content of the acrylic copolymer (A) obtained in Production Example 1 to obtain a one-component composition.
B-1: Dibutyltin bisisooctylthioglycolate B-2: Dibutyltin bisdodecyl mercaptoide B-3: Reaction product of tin oxide and ethyl silicate C-1: Epicoat 828 (manufactured by Japan Epoxy Resin Co., Ltd.) and A1100 One-to-one (molar ratio) reactant C-2 (by Momentive) C-2: bis (triethoxysilylpropyl) amine C-3: bis (trimethoxysilylpropyl) amine C-4: γ-glycidoxypropyltri Methoxysilane C-5: γ-mercaptopropyltrimethoxysilane D-1: adipic acid dimethyl ester E-1: orthoacetic acid ester F-1: 1% methanol solution of concentrated hydrochloric acid Other components: Adeka Resin EP-4100 (Adeka) Made)
<貯蔵安定性>
表1で得られた1液組成物を50℃にて4週間保存した後の性状を確認した。
○:ほとんど増粘なし
△:やや増粘あり
×:著しい増粘あり
<Storage stability>
Properties after storing the one-component composition obtained in Table 1 at 50 ° C. for 4 weeks were confirmed.
○: Almost no thickening Δ: Somewhat thickening ×: There is significant thickening
<密着性>
表1で得られた1液組成物を各種基材に刷毛を用い2回塗布した。23℃で30分放置後、製造例2で得られた弾性シーリング材を用いビード状に打設した。23℃で3日間養生後、さらに、50℃で4日間養生した。カッターナイフで約1cm程度の切込みを入れ、90°ハンドピール試験を行い、破壊状態を観察した(表1に1次と示す)。50℃で4日間養生して得られた被着体を23℃の水に7日間浸漬し、取り出し後、カッターナイフで約1cm程度の切込みを入れ、90°ハンドピール試験を行い、破壊状態を観察した(表1に2次と示す)。
◎:基材にシーラントが残り凝集破壊状態である(凝集破壊率100%)
○:基材にシーラントが残り凝集破壊状態である(凝集破壊率50%以上、100%未満)
△:一部界面で剥離がみられる(凝集破壊率10%以上50%未満)
×:ほとんど界面で剥離している(凝集破壊率10%未満)
<Adhesion>
The one-component composition obtained in Table 1 was applied twice to various substrates using a brush. After standing at 23 ° C. for 30 minutes, the elastic sealing material obtained in Production Example 2 was used to place in a bead shape. After curing at 23 ° C. for 3 days, it was further cured at 50 ° C. for 4 days. A cut of about 1 cm was made with a cutter knife, a 90 ° hand peel test was performed, and the fracture state was observed (shown as primary in Table 1). The adherend obtained by curing at 50 ° C. for 4 days is immersed in water at 23 ° C. for 7 days, taken out, and then cut by about 1 cm with a cutter knife, and a 90 ° hand peel test is conducted. Observed (shown as secondary in Table 1).
A: Sealant remains on the base material and is in a cohesive failure state (cohesive failure rate 100%)
○: The sealant remains on the base material and is in a cohesive failure state (cohesive failure rate of 50% or more and less than 100%)
Δ: Peeling is observed at some interfaces (cohesive failure rate of 10% or more and less than 50%)
X: Peeled almost at the interface (cohesive failure rate of less than 10%)
<ポットライフ>
表1で得られた1液組成物を100mlのディスポカップに約50ml程度入れ、23℃開放系で4時間置いた後、粘度状態を観察した。
○:ほとんど増粘なし
×:表層に皮張りや著しい増粘あり
<Pot life>
About 50 ml of the one-component composition obtained in Table 1 was placed in a 100 ml disposable cup and placed in a 23 ° C. open system for 4 hours, and then the viscosity state was observed.
○: Almost no thickening ×: Skinned or markedly thickened on the surface
Claims (7)
(A)主鎖がアクリル系共重合体鎖を含有し、主鎖末端および/または側鎖に
一般式(I):
(A) The main chain contains an acrylic copolymer chain, and the general formula (I):
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