JP7373770B2 - curable composition - Google Patents
curable composition Download PDFInfo
- Publication number
- JP7373770B2 JP7373770B2 JP2020115184A JP2020115184A JP7373770B2 JP 7373770 B2 JP7373770 B2 JP 7373770B2 JP 2020115184 A JP2020115184 A JP 2020115184A JP 2020115184 A JP2020115184 A JP 2020115184A JP 7373770 B2 JP7373770 B2 JP 7373770B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- group
- meth
- epoxy
- composition
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 74
- -1 ketimine compound Chemical class 0.000 claims description 104
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 49
- 239000004593 Epoxy Substances 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 40
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 38
- 229920000642 polymer Polymers 0.000 claims description 37
- 125000003700 epoxy group Chemical group 0.000 claims description 23
- 150000004658 ketimines Chemical group 0.000 claims description 22
- 230000001070 adhesive effect Effects 0.000 claims description 16
- 239000004014 plasticizer Substances 0.000 claims description 15
- 239000000853 adhesive Substances 0.000 claims description 14
- 229920000193 polymethacrylate Polymers 0.000 claims description 13
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 7
- 229920000058 polyacrylate Polymers 0.000 claims description 6
- 239000000565 sealant Substances 0.000 claims description 5
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical class C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 229910000077 silane Inorganic materials 0.000 claims description 3
- 239000004841 bisphenol A epoxy resin Substances 0.000 claims 2
- 239000004842 bisphenol F epoxy resin Substances 0.000 claims 2
- 239000000047 product Substances 0.000 description 44
- 239000003822 epoxy resin Substances 0.000 description 19
- 229920000647 polyepoxide Polymers 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 10
- 150000003141 primary amines Chemical class 0.000 description 10
- 239000000945 filler Substances 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 6
- 239000006096 absorbing agent Substances 0.000 description 5
- 239000004566 building material Substances 0.000 description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 238000009864 tensile test Methods 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 125000005370 alkoxysilyl group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000003566 sealing material Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 229960000834 vinyl ether Drugs 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-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
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- KCXZNSGUUQJJTR-UHFFFAOYSA-N Di-n-hexyl phthalate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC KCXZNSGUUQJJTR-UHFFFAOYSA-N 0.000 description 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group 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
- 230000006750 UV protection Effects 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 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 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000004035 construction material Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 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
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 description 1
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 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
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical group COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 description 1
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical group C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 description 1
- ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical group C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 description 1
- MWZJGRDWJVHRDV-UHFFFAOYSA-N 1,4-bis(ethenoxy)butane Chemical group C=COCCCCOC=C MWZJGRDWJVHRDV-UHFFFAOYSA-N 0.000 description 1
- DQNSRQYYCSXZDF-UHFFFAOYSA-N 1,4-bis(ethenoxymethyl)cyclohexane Chemical group C=COCC1CCC(COC=C)CC1 DQNSRQYYCSXZDF-UHFFFAOYSA-N 0.000 description 1
- JOSFJABFAXRZJQ-UHFFFAOYSA-N 1,6-bis(ethenoxy)hexane Chemical group C=COCCCCCCOC=C JOSFJABFAXRZJQ-UHFFFAOYSA-N 0.000 description 1
- UEIPWOFSKAZYJO-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-[2-(2-ethenoxyethoxy)ethoxy]ethane Chemical group C=COCCOCCOCCOCCOC=C UEIPWOFSKAZYJO-UHFFFAOYSA-N 0.000 description 1
- UNMYKPSSIFZORM-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)butane Chemical group CCCCOCCOC=C UNMYKPSSIFZORM-UHFFFAOYSA-N 0.000 description 1
- ZRZHXNCATOYMJH-UHFFFAOYSA-N 1-(chloromethyl)-4-ethenylbenzene Chemical compound ClCC1=CC=C(C=C)C=C1 ZRZHXNCATOYMJH-UHFFFAOYSA-N 0.000 description 1
- RJTJPFYIGZWFMK-UHFFFAOYSA-N 1-[2-(2-ethenoxyethoxy)ethoxy]-2-methoxyethane Chemical group COCCOCCOCCOC=C RJTJPFYIGZWFMK-UHFFFAOYSA-N 0.000 description 1
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical group O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical group O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- SJLLJZNSZJHXQN-UHFFFAOYSA-N 1-dodecylpyrrole-2,5-dione Chemical group CCCCCCCCCCCCN1C(=O)C=CC1=O SJLLJZNSZJHXQN-UHFFFAOYSA-N 0.000 description 1
- CZAVRNDQSIORTH-UHFFFAOYSA-N 1-ethenoxy-2,2-bis(ethenoxymethyl)butane Chemical compound C=COCC(CC)(COC=C)COC=C CZAVRNDQSIORTH-UHFFFAOYSA-N 0.000 description 1
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical group C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical group CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical group CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- LAYAKLSFVAPMEL-UHFFFAOYSA-N 1-ethenoxydodecane Chemical group CCCCCCCCCCCCOC=C LAYAKLSFVAPMEL-UHFFFAOYSA-N 0.000 description 1
- QJJDJWUCRAPCOL-UHFFFAOYSA-N 1-ethenoxyoctadecane Chemical group CCCCCCCCCCCCCCCCCCOC=C QJJDJWUCRAPCOL-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical group CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- GRFNSWBVXHLTCI-UHFFFAOYSA-N 1-ethenyl-4-[(2-methylpropan-2-yl)oxy]benzene Chemical compound CC(C)(C)OC1=CC=C(C=C)C=C1 GRFNSWBVXHLTCI-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical group O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- XPZBNIUWMDJFPW-UHFFFAOYSA-N 2,2,3-trimethylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1(C)C XPZBNIUWMDJFPW-UHFFFAOYSA-N 0.000 description 1
- AVFZQHWFGFKQIG-UHFFFAOYSA-N 2,2,3-trimethylcyclopentan-1-one Chemical compound CC1CCC(=O)C1(C)C AVFZQHWFGFKQIG-UHFFFAOYSA-N 0.000 description 1
- ZTXZCWMXSBARIF-UHFFFAOYSA-N 2-(1-phenylethylideneamino)-N-[2-(1-phenylethylideneamino)ethyl]ethanamine Chemical compound C1(=CC=CC=C1)C(C)=NCCNCCN=C(C)C1=CC=CC=C1 ZTXZCWMXSBARIF-UHFFFAOYSA-N 0.000 description 1
- WULAHPYSGCVQHM-UHFFFAOYSA-N 2-(2-ethenoxyethoxy)ethanol Chemical compound OCCOCCOC=C WULAHPYSGCVQHM-UHFFFAOYSA-N 0.000 description 1
- CJAGRJAFLCPABV-UHFFFAOYSA-N 2-(4-methylpentan-2-ylideneamino)-n-[2-(4-methylpentan-2-ylideneamino)ethyl]ethanamine Chemical compound CC(C)CC(C)=NCCNCCN=C(C)CC(C)C CJAGRJAFLCPABV-UHFFFAOYSA-N 0.000 description 1
- NOJHYEMRGGBHOI-UHFFFAOYSA-N 2-(butan-2-ylideneamino)-n-[2-(butan-2-ylideneamino)ethyl]ethanamine Chemical compound CCC(C)=NCCNCCN=C(C)CC NOJHYEMRGGBHOI-UHFFFAOYSA-N 0.000 description 1
- SFRDXVJWXWOTEW-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)CO SFRDXVJWXWOTEW-UHFFFAOYSA-N 0.000 description 1
- CLSFJOSFPTTYLQ-UHFFFAOYSA-N 2-(methylideneamino)-n-[2-(methylideneamino)ethyl]ethanamine Chemical compound C=NCCNCCN=C CLSFJOSFPTTYLQ-UHFFFAOYSA-N 0.000 description 1
- YWYQDZVBTQIBAL-UHFFFAOYSA-N 2-(pentan-3-ylideneamino)-n-[2-(pentan-3-ylideneamino)ethyl]ethanamine Chemical compound CCC(CC)=NCCNCCN=C(CC)CC YWYQDZVBTQIBAL-UHFFFAOYSA-N 0.000 description 1
- FPHDXPRLWRPJNS-UHFFFAOYSA-N 2-(propan-2-ylideneamino)-n-[2-(propan-2-ylideneamino)ethyl]ethanamine Chemical compound CC(C)=NCCNCCN=C(C)C FPHDXPRLWRPJNS-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- CYADZXMTKIHVMV-UHFFFAOYSA-N 2-ethenoxy-2-methylbutane Chemical group CCC(C)(C)OC=C CYADZXMTKIHVMV-UHFFFAOYSA-N 0.000 description 1
- PGYJSURPYAAOMM-UHFFFAOYSA-N 2-ethenoxy-2-methylpropane Chemical group CC(C)(C)OC=C PGYJSURPYAAOMM-UHFFFAOYSA-N 0.000 description 1
- PLWQJHWLGRXAMP-UHFFFAOYSA-N 2-ethenoxy-n,n-diethylethanamine Chemical compound CCN(CC)CCOC=C PLWQJHWLGRXAMP-UHFFFAOYSA-N 0.000 description 1
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical compound OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- VYVFQBFOMKEKBG-UHFFFAOYSA-L 3,3-dibutyl-2,4,3-benzodioxastannepine-1,5-dione Chemical compound O=C1O[Sn](CCCC)(CCCC)OC(=O)C2=CC=CC=C21 VYVFQBFOMKEKBG-UHFFFAOYSA-L 0.000 description 1
- DSSAWHFZNWVJEC-UHFFFAOYSA-N 3-(ethenoxymethyl)heptane Chemical group CCCCC(CC)COC=C DSSAWHFZNWVJEC-UHFFFAOYSA-N 0.000 description 1
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- NBJODVYWAQLZOC-UHFFFAOYSA-L [dibutyl(octanoyloxy)stannyl] octanoate Chemical compound CCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCC NBJODVYWAQLZOC-UHFFFAOYSA-L 0.000 description 1
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
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- 238000007259 addition reaction Methods 0.000 description 1
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- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
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- 239000000470 constituent Substances 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- ISXDVFNOXYQPIA-UHFFFAOYSA-N dibutyl pentanedioate Chemical compound CCCCOC(=O)CCCC(=O)OCCCC ISXDVFNOXYQPIA-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- XBGSYTUNSOYWEF-UHFFFAOYSA-N dibutyltin;dodecanoic acid Chemical compound CCCC[Sn]CCCC.CCCCCCCCCCCC(O)=O XBGSYTUNSOYWEF-UHFFFAOYSA-N 0.000 description 1
- ODADONMDNZJQMW-UHFFFAOYSA-N diethoxy-ethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](CC)(OCC)CCCOCC1CO1 ODADONMDNZJQMW-UHFFFAOYSA-N 0.000 description 1
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- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical group CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
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- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 125000005474 octanoate group Chemical group 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- JQCXWCOOWVGKMT-UHFFFAOYSA-N phthalic acid diheptyl ester Natural products CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000012945 sealing adhesive Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 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
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical group C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- INRGAWUQFOBNKL-UHFFFAOYSA-N {4-[(Vinyloxy)methyl]cyclohexyl}methanol Chemical compound OCC1CCC(COC=C)CC1 INRGAWUQFOBNKL-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Description
本発明は、硬化性組成物に関し、詳しくはシーリング材、接着剤などとして使用可能な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 that can be used as a sealant, adhesive, or the like.
特許文献１には、接着剤として使用可能な組成物として、加水分解性シリル基を有するポリアルキレンオキサイド、エポキシ樹脂、エポキシシランカップリング剤、ケチミン化合物、及び脂肪酸処理酸化カルシウムを含有し、エポキシ樹脂のエポキシ基の総モル数とケチミン化合物の加水分解物であるアミン化合物が有しているアミノ基の総モル数との比（エポキシ樹脂のエポキシ基の総モル数／ケチミン化合物の加水分解物であるアミン化合物が有しているアミノ基の総モル数）が０．７～１．２である接着剤組成物が、開示されている。 Patent Document 1 describes a composition that can be used as an adhesive, which contains a polyalkylene oxide having a hydrolyzable silyl group, an epoxy resin, an epoxy silane coupling agent, a ketimine compound, and fatty acid-treated calcium oxide, and contains an epoxy resin. The ratio of the total number of moles of epoxy groups in the epoxy resin to the total number of moles of amino groups in the amine compound that is the hydrolyzate of the ketimine compound (total number of moles of epoxy groups in the epoxy resin/the hydrolyzate of the ketimine compound) An adhesive composition is disclosed in which an amine compound has a total number of moles of amino groups of 0.7 to 1.2.
発明者が研究開発を進めた結果得られた知見によると、特許文献１に開示されている組成物を接着剤などとして利用した場合、組成物の硬化物が経時的に硬く脆くなり、機械的な負荷や熱による膨張、収縮などによってひび割れなどの破損が生じやすくなることがある。 According to the knowledge obtained as a result of the inventor's research and development, when the composition disclosed in Patent Document 1 is used as an adhesive, the cured product of the composition becomes hard and brittle over time, resulting in mechanical damage. Damage such as cracks may occur easily due to heavy loads and expansion and contraction caused by heat.
本発明の課題は、硬化させて得られる硬化物に、経時的な硬さの増大が生じにくい硬化性組成物を提供することである。 An object of the present invention is to provide a curable composition whose hardness is less likely to increase over time in a cured product obtained by curing.
本発明の一態様に係る硬化性組成物は、架橋性シリル基を有する重合体（Ａ）と、エポキシ化合物（Ｂ）と、ケチミン化合物（Ｃ）とを含有し、前記エポキシ化合物（Ｂ）の有するエポキシ基に対する、前記ケチミン化合物（Ｃ）の有するケチミン構造のモル比が、０．４以上０．８以下である。 A curable composition according to one embodiment of the present invention contains a polymer (A) having a crosslinkable silyl group, an epoxy compound (B), and a ketimine compound (C), The molar ratio of the ketimine structure of the ketimine compound (C) to the epoxy group thereof is 0.4 or more and 0.8 or less.
本発明によると、硬化させて得られる硬化物に、経時的な硬さの増大が生じにくい硬化性組成物を提供できる。 According to the present invention, it is possible to provide a curable composition whose hardness is less likely to increase over time in a cured product obtained by curing.
以下、本発明の一実施形態について説明する。 An embodiment of the present invention will be described below.
本実施形態では、硬化性組成物（以下、組成物（Ｘ）ともいう）は、架橋性シリル基を有する重合体（Ａ）と、エポキシ化合物（Ｂ）と、ケチミン化合物（Ｃ）とを含有する。エポキシ化合物（Ｂ）の有するエポキシ基に対する、ケチミン化合物（Ｃ）の有するケチミン構造のモル比は、０．４以上０．８以下である。なお、ケチミン構造とは、ケトンに由来するアミノ基であり、例えば－Ｎ＝Ｃ（Ｒ）Ｒ’という構造を有する。Ｒ及びＲ’の各々は水素ではない有機基であって、例えばアルキル基である。ケチミン構造は加水分解によって、一級アミノ基（－ＮＨ2）とケトン（Ｒ－ＣＯ－Ｒ’）とを生成する。 In this embodiment, the curable composition (hereinafter also referred to as composition (X)) contains a polymer (A) having a crosslinkable silyl group, an epoxy compound (B), and a ketimine compound (C). do. The molar ratio of the ketimine structure of the ketimine compound (C) to the epoxy group of the epoxy compound (B) is 0.4 or more and 0.8 or less. Note that the ketimine structure is an amino group derived from a ketone, and has, for example, a structure of -N=C(R)R'. Each of R and R' is an organic group that is not hydrogen, such as an alkyl group. The ketimine structure generates a primary amino group (-NH 2 ) and a ketone (R-CO-R') by hydrolysis.
本実施形態によると、組成物（Ｘ）を硬化させて得られる硬化物は良好な柔軟性を有しやすい。このため組成物（Ｘ）をシーリング材、接着剤などとして使用できる。また、硬化物には経時的な硬さの増大が生じにくい。その理由は、次のとおりであると推察される。 According to this embodiment, the cured product obtained by curing the composition (X) tends to have good flexibility. Therefore, composition (X) can be used as a sealant, adhesive, etc. Furthermore, the hardness of the cured product is less likely to increase over time. The reason is presumed to be as follows.
組成物（Ｘ）が硬化する際には、重合体（Ａ）が架橋性シリル基を介して重合することで高分子化する。また、ケチミン化合物（Ｃ）は、まず空気中の水分などと反応することで加水分解し、一級アミンとケトンとを生成する。一級アミンはエポキシ化合物（Ｂ）と反応して高分子化する。一級アミンにおける一つの一級アミノ基とエポキシ化合物（Ｂ）における一つのエポキシ基とが反応すると、二級アミノ基が生成する。この二級アミノ基が更にエポキシ化合物（Ｂ）における別のエポキシ基と反応すると三級アミノ基が生成する。これにより、エポキシ化合物（Ｂ）の二つの分子が三級アミノ基を介して結合する架橋構造が生じ、高分子マトリックスが形成される。これにより、硬化物が作製される。本実施形態では、エポキシ基に対するケチミン構造のモル比が０．４以上であることで、ケチミン化合物（Ｃ）を利用したエポキシ化合物（Ｂ）の架橋を十分に進行させることができ、このためシーリング材、接着剤などとして好適な硬化物を得ることができる。また、エポキシ基に対するケチミン構造のモル比が０．８以下であることで、ケチミン化合物（Ｃ）がエポキシ化合物（Ｂ）との反応で消費されやすい。そのため、硬化物中に未反応のケチミン化合物（Ｃ）が残存しにくい。未反応のケチミン化合物（Ｃ）は経時的にエポキシ残基に作用して架橋点を増やすことで、硬化物の弾性率を増大させることがあるが、ケチミン化合物（Ｃ）が残存しにくいと、このような弾性率の増大は生じにくい。また、未反応のケチミン化合物（Ｃ）は例えば温水などで加熱されると加水分解によって一級アミンを生成し、更に一級アミンの分子同士が反応したり、一級アミンが二酸化炭素と反応したりして、硬くて脆い生成物を生じやすい。しかし、ケチミン化合物（Ｃ）が残存しにくいと、このような生成物は生じにくい。また、モル比が０．８以下であると、二級アミノ基とエポキシ基との反応が進行しやすく、そのため硬化物中に二級アミノ基が残存しにくい。硬化物中の二級アミノ基も例えば温水などで加熱されると二酸化炭素と反応して硬くて脆い生成物を生じやすいが、二級アミノ基が残存しにくいとこのような生成物は生じにくい。このため、硬化物の経時的な弾性率の増大が生じにくいと考えられる。 When the composition (X) is cured, the polymer (A) is polymerized via the crosslinkable silyl group, thereby becoming a polymer. In addition, the ketimine compound (C) is first hydrolyzed by reacting with moisture in the air to generate a primary amine and a ketone. The primary amine reacts with the epoxy compound (B) to form a polymer. When one primary amino group in the primary amine and one epoxy group in the epoxy compound (B) react, a secondary amino group is generated. When this secondary amino group further reacts with another epoxy group in the epoxy compound (B), a tertiary amino group is generated. As a result, a crosslinked structure in which two molecules of the epoxy compound (B) are bonded via the tertiary amino group is generated, and a polymer matrix is formed. In this way, a cured product is produced. In this embodiment, by setting the molar ratio of the ketimine structure to the epoxy group to be 0.4 or more, crosslinking of the epoxy compound (B) using the ketimine compound (C) can proceed sufficiently, and therefore the sealing A cured product suitable for use as materials, adhesives, etc. can be obtained. Furthermore, when the molar ratio of the ketimine structure to the epoxy group is 0.8 or less, the ketimine compound (C) is likely to be consumed in the reaction with the epoxy compound (B). Therefore, unreacted ketimine compound (C) is unlikely to remain in the cured product. Unreacted ketimine compound (C) acts on epoxy residues over time and increases the number of crosslinking points, which may increase the elastic modulus of the cured product, but if ketimine compound (C) is difficult to remain, Such an increase in elastic modulus is unlikely to occur. In addition, when the unreacted ketimine compound (C) is heated with hot water, for example, it generates a primary amine through hydrolysis, and the primary amine molecules further react with each other, or the primary amine reacts with carbon dioxide. , tend to produce hard and brittle products. However, if the ketimine compound (C) is less likely to remain, such products are less likely to be produced. Moreover, when the molar ratio is 0.8 or less, the reaction between the secondary amino group and the epoxy group tends to proceed, and therefore the secondary amino group is difficult to remain in the cured product. When the secondary amino groups in the cured product are heated with hot water, for example, they tend to react with carbon dioxide and produce hard and brittle products, but such products are difficult to produce if the secondary amino groups are hard to remain. . Therefore, it is considered that the elastic modulus of the cured product is unlikely to increase over time.
組成物（Ｘ）の成分について更に詳しく説明する。 The components of composition (X) will be explained in more detail.
上述のとおり、重合体（Ａ）は、架橋性シリル基を有する。架橋性シリル基とは、ケイ素原子と、ケイ素原子に結合している加水分解性基とを有する基である。一つの架橋性シリル基において、一つのケイ素原子に、例えば１～３個の加水分解性基が結合されている。加水分解性基は、例えば水素原子、アルコキシ基、アシルオキシ基、ケトキシメート基、酸アミド基、アミノオキシ基、メルカプト基及びアルケニルオキシ基等からなる群から選択される少なくとも一種の基を含む。加水分解性基はアルコキシ基を含むことが好ましい。すなわち、架橋性シリル基はアルコキシシリル基を含むことが好ましい。 As mentioned above, the polymer (A) has a crosslinkable silyl group. A crosslinkable silyl group is a group having a silicon atom and a hydrolyzable group bonded to the silicon atom. In one crosslinkable silyl group, for example, 1 to 3 hydrolyzable groups are bonded to one silicon atom. The hydrolyzable group includes, for example, at least one group selected from the group consisting of a hydrogen atom, an alkoxy group, an acyloxy group, a ketoximate group, an acid amide group, an aminooxy group, a mercapto group, an alkenyloxy group, and the like. Preferably, the hydrolyzable group contains an alkoxy group. That is, it is preferable that the crosslinkable silyl group contains an alkoxysilyl group.
アルコキシシリル基は、例えばトリメトキシシリル基、トリエトキシシリル基、トリイソプロポキシシリル基、及びトリフェノキシシリル基などのトリアルコキシシリル基；ジメトキシメチルシリル基、及びジエトキシメチルシリル基などのジメトキシシリル基；並びに、メトキシジメトキシシリル基、及びエトキシジメチルシリル基などのモノアルコキシシリル基からなる群から選択される少なくとも一種の基を含む。アルコキシシリル基がジメトキシシリル基とトリメトキシシリル基とのうち少なくとも一方を含むことが特に好ましい。 Alkoxysilyl groups include, for example, trialkoxysilyl groups such as trimethoxysilyl group, triethoxysilyl group, triisopropoxysilyl group, and triphenoxysilyl group; dimethoxysilyl groups such as dimethoxymethylsilyl group and diethoxymethylsilyl group. ; and at least one group selected from the group consisting of a methoxydimethoxysilyl group and a monoalkoxysilyl group such as an ethoxydimethylsilyl group. It is particularly preferred that the alkoxysilyl group contains at least one of a dimethoxysilyl group and a trimethoxysilyl group.
重合体（Ａ）の一分子当たりの架橋性シリル基の平均個数は１個以上３個以下であることが好ましい。 The average number of crosslinkable silyl groups per molecule of the polymer (A) is preferably 1 or more and 3 or less.
重合体（Ａ）は、架橋性シリル基を有するのであれば、種々の骨格を有してよい。例えば重合体（Ａ）は、ポリオキシアルキレン骨格、ビニル変性ポリオキシアルキレン骨格、ポリ（メタ）アクリレート骨格、ビニル系重合体を含む骨格、及びポリエステル骨格等からなる群から選択される少なくとも一種の骨格を有してもよい。重合体（Ａ）の骨格はオルガノシロキサンを含んでもよい。 The polymer (A) may have various skeletons as long as it has a crosslinkable silyl group. For example, the polymer (A) has at least one skeleton selected from the group consisting of a polyoxyalkylene skeleton, a vinyl-modified polyoxyalkylene skeleton, a poly(meth)acrylate skeleton, a skeleton containing a vinyl polymer, a polyester skeleton, etc. It may have. The skeleton of the polymer (A) may contain organosiloxane.
重合体（Ａ）は、ポリオキシアルキレン骨格とポリ（メタ）アクリレート骨格とのうち少なくとも一方を有することが好ましい。この場合、組成物（Ｘ）はシーリング材、接着剤等として好適な物性を有しやすい。特に重合体（Ａ）がポリ（メタ）アクリレート骨格を有する場合には、組成物（Ｘ）及びその硬化物は良好な耐候性及び耐ＵＶ性を有しやすい。 It is preferable that the polymer (A) has at least one of a polyoxyalkylene skeleton and a poly(meth)acrylate skeleton. In this case, the composition (X) tends to have physical properties suitable for use as a sealant, adhesive, etc. In particular, when the polymer (A) has a poly(meth)acrylate skeleton, the composition (X) and its cured product tend to have good weather resistance and UV resistance.
重合体（Ａ）は、例えばポリオキシアルキレン骨格を有する重合体（Ａ１）と、ポリ（メタ）アクリレート骨格を有する重合体（Ａ２）とのうち、少なくとも一方を含有する。 The polymer (A) contains, for example, at least one of a polymer (A1) having a polyoxyalkylene skeleton and a polymer (A2) having a poly(meth)acrylate skeleton.
重合体（Ａ１）は、例えばポリオキシアルキレン骨格と、ポリオキシアルキレン骨格に結合している架橋性シリル基とを有する。重合体（Ａ１）は、一分子あたり少なくとも一個の架橋性シリル基を有する。架橋性シリル基は、ポリオキシアルキレン骨格の途中に側鎖として結合してもよく、ポリオキシアルキレン骨格の末端に結合していてもよい。架橋性シリル基は、ポリオキシアルキレン骨格の末端にウレタン結合を介して結合していてもよい。 The polymer (A1) has, for example, a polyoxyalkylene skeleton and a crosslinkable silyl group bonded to the polyoxyalkylene skeleton. The polymer (A1) has at least one crosslinkable silyl group per molecule. The crosslinkable silyl group may be bonded as a side chain in the middle of the polyoxyalkylene skeleton, or may be bonded to the end of the polyoxyalkylene skeleton. The crosslinkable silyl group may be bonded to the terminal of the polyoxyalkylene skeleton via a urethane bond.
ポリオキシアルキレン骨格は、例えば－（Ｒ－Ｏ）n－という式で表される。Ｒはアルキレン基であり、アルキレン基の炭素数は例えば１以上１４以下である。ｎは二以上の自然数である。一つのポリアルキレン骨格中の複数のＲは互いに同一であっても異なっていてもよい。 The polyoxyalkylene skeleton is represented by the formula -(RO)n-, for example. R is an alkylene group, and the number of carbon atoms in the alkylene group is, for example, 1 or more and 14 or less. n is a natural number of 2 or more. A plurality of R's in one polyalkylene skeleton may be the same or different.
ポリオキシアルキレン骨格は、例えばエチレンオキサイド単位、プロピレンオキサイド単位、ブチレンオキサイド単位、及びテトラメチレンオキサイド単位等からなる群から選択される少なくとも一種の構成単位を有する。 The polyoxyalkylene skeleton has at least one constituent unit selected from the group consisting of, for example, ethylene oxide units, propylene oxide units, butylene oxide units, and tetramethylene oxide units.
ポリオキシアルキレン骨格は、エチレングリコールを出発原料として用いた２官能のものと、２－ヒドロキシメチルプロパン１，３－ジオールを出発原料とした３官能のものの少なくとも一方を含むものであることが好ましい。 The polyoxyalkylene skeleton preferably contains at least one of a bifunctional one using ethylene glycol as a starting material and a trifunctional one using 2-hydroxymethylpropane 1,3-diol as a starting material.
重合体（Ａ１）の重量平均分子量は、８０００以上２５０００以下であることが好ましい。重量平均分子量が８０００以上であることで組成物（Ｘ）の硬化物は良好な柔軟性を有しやすい。また、重量平均分子量が２５０００以下であることで、組成物（Ｘ）の粘度が大きくなりにくく、そのため組成物（Ｘ）の塗布性が良好になりやすい。重量平均分子量は１５０００以上２００００以下であればより好ましい。なお、重量平均分子量は、ＧＰＣ（ゲル浸透クロマトグラフィー）による測定結果からスチレン換算で得られる値である。 The weight average molecular weight of the polymer (A1) is preferably 8,000 or more and 25,000 or less. When the weight average molecular weight is 8000 or more, the cured product of composition (X) tends to have good flexibility. Furthermore, when the weight average molecular weight is 25,000 or less, the viscosity of the composition (X) is unlikely to increase, and therefore the coating properties of the composition (X) tend to be good. The weight average molecular weight is more preferably 15,000 or more and 20,000 or less. Note that the weight average molecular weight is a value obtained in terms of styrene from measurement results by GPC (gel permeation chromatography).
一方、重合体（Ａ２）は、ポリ（メタ）アクリレート骨格と、ポリ（メタ）アクリレート骨格に結合している架橋性シリル基とを有する。重合体（Ａ２）は、一分子あたり少なくとも一個の架橋性シリル基を有する。架橋性シリル基は、ポリ（メタ）アクリレート骨格の途中に側鎖として結合してもよく、ポリ（メタ）アクリレート骨格の末端に結合していてもよい。ポリ（メタ）アクリレート骨格の一方の末端に一個の架橋性シリル基が結合し、かつ側鎖に１個以上の架橋性シリル基が結合していることが好ましい。ポリ（メタ）アクリレート骨格の両末端のみに架橋性シリル基が結合している場合は後架橋の影響を受けて硬化物が硬くなりやすく、ポリ（メタ）アクリレート骨格の側鎖のみに架橋性シリル基が結合している場合はアクリル側鎖の加水分解により硬化物の強度低下を引き起こす可能性がある。 On the other hand, the polymer (A2) has a poly(meth)acrylate skeleton and a crosslinkable silyl group bonded to the poly(meth)acrylate skeleton. The polymer (A2) has at least one crosslinkable silyl group per molecule. The crosslinkable silyl group may be bonded as a side chain in the middle of the poly(meth)acrylate skeleton, or may be bonded to the end of the poly(meth)acrylate skeleton. It is preferable that one crosslinkable silyl group is bonded to one end of the poly(meth)acrylate skeleton, and one or more crosslinkable silyl groups are bonded to the side chain. If crosslinkable silyl groups are bonded only to both ends of the poly(meth)acrylate skeleton, the cured product is likely to become hard due to the influence of post-crosslinking. If groups are bonded, hydrolysis of the acrylic side chains may cause a decrease in strength of the cured product.
ポリ（メタ）アクリレート骨格は、（メタ）アクリル化合物を含む不飽和単量体が重合した構造を有する。（メタ）アクリル化合物は、アクリル化合物とメタクリル化合物とのうち少なくとも一方からなる。（メタ）アクリル化合物は、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及び（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及び（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及び（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、及び（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等からなる群から選択される少なくとも一種の成分を含有することができる。なお、（メタ）アクリル化合物が含みうる成分は前記のみには制限されない。 The poly(meth)acrylate skeleton has a structure in which unsaturated monomers containing a (meth)acrylic compound are polymerized. The (meth)acrylic compound consists of at least one of an acrylic compound and a methacrylic compound. Examples of (meth)acrylic compounds include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, ( Isobutyl meth)acrylate, s-butyl (meth)acrylate, t-butyl (meth)acrylate, n-pentyl (meth)acrylate, neopentyl (meth)acrylate, n-hexyl (meth)acrylate , n-heptyl (meth)acrylate, n-octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate , alkyl (meth)acrylates such as dodecyl (meth)acrylate, lauryl (meth)acrylate, tridecyl (meth)acrylate, and stearyl (meth)acrylate; cyclohexyl (meth)acrylate, isobornyl (meth)acrylate and alicyclic alkyl acrylates such as tricyclodecynyl (meth)acrylate; aromatic acrylic esters such as phenyl (meth)acrylate, toluyl (meth)acrylate and benzyl (meth)acrylate; ) Hydroxyalkyl (meth)acrylates such as hydroxyethyl acrylate, hydroxybutyl (meth)acrylate, hydroxypropyl (meth)acrylate, and ε-caprolactone addition reaction product of hydroxyethyl (meth)acrylate; (meth)acrylate 2-methoxyethyl acid, 3-methoxybutyl (meth)acrylate, 2-aminoethyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, chloroethyl (meth)acrylate, trifluoroethyl (meth)acrylate , trifluoromethylmethyl (meth)acrylate, and heteroatom-containing acrylic esters such as tetrahydrofurfuryl (meth)acrylate. Note that the components that the (meth)acrylic compound may contain are not limited to the above.
ポリ（メタ）アクリレート骨格を構成する不飽和単量体は、（メタ）アクリル化合物のみを含有してもよく、（メタ）アクリル化合物とそれ以外の単量体とを含有してもよい。（メタ）アクリル化合物以外の単量体は、例えばスチレン、インデン、α－メチルスチレン、ｐ－メチルスチレン、ｐ－クロロスチレン、ｐ－クロロメチルスチレン、ｐ－メトキシスチレン、ｐ－ｔｅｒｔ－ブトキシスチレン、ジビニルベンゼンなどのスチレン誘導体、酢酸ビニル、プロピオン酸ビニル、酪酸ビニル、カプロン酸ビニル、安息香酸ビニル、珪皮酸ビニルなどのビニルエステル基を持つ化合物、無水マレイン酸、Ｎ－ビニルピロリドン、Ｎ－ビニルモルフォリン、メタクリロニトリル、アクリロニトリル、アクリルアミド、メタクリルアミド、Ｎ－シクロヘキシルマレイミド、Ｎ－フェニルマレイミド、Ｎ－ラウリルマレイミド、Ｎ－ベンジルマレイミド、ｎ－プロピルビニルエーテル、ｎ－ブチルビニルエーテル、イソブチルビニルエーテル、ｔｅｒｔ－ブチルビニルエーテル、ｔｅｒｔ－アミルビニルエーテル、シクロヘキシルビニルエーテル、２－エチルヘキシルビニルエーテル、ドデシルビニルエーテル、オクタデシルビニルエーテル、２－クロロエチルビニルエーテル、エチレングリコールブチルビニルエーテル、トリエチレングリコールメチルビニルエーテル、安息香酸（４－ビニロキシ）ブチル、エチレングリコールジビニルエーテル、ジエチレングリコールジビニルエーテル、トリエチレングリコールジビニルエーテル、テトラエチレングリコールジビニルエーテル、ブタン－１，４－ジオール－ジビニルエーテル、ヘキサン－１，６－ジオール－ジビニルエーテル、シクロヘキサン－１，４－ジメタノール－ジビニルエーテル、イソフタル酸ジ（４－ビニロキシ）ブチル、グル
タル酸ジ（４－ビニロキシ）ブチル、コハク酸ジ（４－ビニロキシ）ブチルトリメチロールプロパントリビニルエーテル、２－ヒドロキシエチルビニルエーテル、４－ヒドロキシブチルビニルエーテル、６－ヒドロキシヘキシルビニルエーテル、シクロヘキサン－１，４－ジメタノールモノビニルエーテル、ジエチレングリコールモノビニルエーテル、３－アミノプロピルビニルエーテル、２－（Ｎ，Ｎ－ジエチルアミノ）エチルビニルエーテル、ウレタンビニルエーテル、及びポリエステルビニルエーテルなどのビニロキシ基を持つ化合物などからなる群から選択される少なくとも一種の化合物を含む。
The unsaturated monomer constituting the poly(meth)acrylate skeleton may contain only a (meth)acrylic compound, or may contain a (meth)acrylic compound and other monomers. Monomers other than (meth)acrylic compounds include, for example, styrene, indene, α-methylstyrene, p-methylstyrene, p-chlorostyrene, p-chloromethylstyrene, p-methoxystyrene, p-tert-butoxystyrene, Styrene derivatives such as divinylbenzene, compounds with vinyl ester groups such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl caproate, vinyl benzoate, vinyl cinnamate, maleic anhydride, N-vinylpyrrolidone, N-vinyl Morpholine, methacrylonitrile, acrylonitrile, acrylamide, methacrylamide, N-cyclohexylmaleimide, N-phenylmaleimide, N-laurylmaleimide, N-benzylmaleimide, n-propyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, tert-butyl Vinyl ether, tert-amyl vinyl ether, cyclohexyl vinyl ether, 2-ethylhexyl vinyl ether, dodecyl vinyl ether, octadecyl vinyl ether, 2-chloroethyl vinyl ether, ethylene glycol butyl vinyl ether, triethylene glycol methyl vinyl ether, (4-vinyloxy)butyl benzoate, ethylene glycol di Vinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, tetraethylene glycol divinyl ether, butane-1,4-diol-divinyl ether, hexane-1,6-diol-divinyl ether, cyclohexane-1,4-dimethanol-divinyl ether Vinyl ether, di(4-vinyloxy)butyl isophthalate, di(4-vinyloxy)butyl glutarate, di(4-vinyloxy)butyl succinate, trimethylolpropane trivinyl ether, 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, 6 -Having a vinyloxy group such as hydroxyhexyl vinyl ether, cyclohexane-1,4-dimethanol monovinyl ether, diethylene glycol monovinyl ether, 3-aminopropyl vinyl ether, 2-(N,N-diethylamino)ethyl vinyl ether, urethane vinyl ether, and polyester vinyl ether Contains at least one compound selected from the group consisting of compounds, etc.
重合体（Ａ２）の重量平均分子量は、１００００以上７００００以下であることが好ましい。重量平均分子量が１００００以上であることで組成物（Ｘ）の硬化物は良好な柔軟性を有しやすい。また、重量平均分子量が７００００以下であることで、組成物（Ｘ）の粘度が大きくなりにくく、そのため組成物（Ｘ）の塗布性が良好になりやすい。重量平均分子量は２００００以上６００００以下であればより好ましい。なお、重量平均分子量は、ＧＰＣ（ゲル浸透クロマトグラフィー）による測定結果からスチレン換算で得られる値である。 The weight average molecular weight of the polymer (A2) is preferably 10,000 or more and 70,000 or less. When the weight average molecular weight is 10,000 or more, the cured product of composition (X) tends to have good flexibility. Furthermore, when the weight average molecular weight is 70,000 or less, the viscosity of the composition (X) is unlikely to increase, and therefore the coating properties of the composition (X) tend to be good. The weight average molecular weight is more preferably 20,000 or more and 60,000 or less. Note that the weight average molecular weight is a value obtained in terms of styrene from measurement results by GPC (gel permeation chromatography).
エポキシ化合物（Ｂ）は、一分子中に少なくとも一つのエポキシ基を有する。エポキシ化合物（Ｂ）によって、硬化物が良好な接着性を有しやすい。エポキシ化合物（Ｂ）は、例えばビスフェノールＡ型エポキシ樹脂、ビスフェノールＦ型エポキシ樹脂、水添ビスフェノールＡ型エポキシ樹脂、水添ビスフェノールＦ型エポキシ樹脂、グリシジルエステル型エポキシ樹脂、ノボラック型エポキシ樹脂、ウレタン変性エポキシ樹脂、メタキシレンジやヒダントインなどをエポキシ化した含窒素エポキシ樹脂、ポリブタジエン又はＮＢＲ（アクリロニトリル－ブタジエン共重合体）を含有するゴム変性エポキシ樹脂、及びエポキシシランからなる群から選択される少なくとも一種の化合物を含有する。エポキシシランは、例えば３－グリシドキシプロピルトリメトキシシラン、３－グリシドキシプロピルトリエトキシシラン、３－グリシドキシプロピルメチルジメトキシシラン、３－グリシドキシプロピルエチルジエトキシシラン、及び２－（３，４エポキシシクロヘキシル）エチルトリメトキシシラン等からなる群から選択される少なくとも一種の化合物を含有する。なお、エポキシ化合物（Ｂ）に含まれる成分は前記のみには制限されない。 The epoxy compound (B) has at least one epoxy group in one molecule. The cured product tends to have good adhesive properties due to the epoxy compound (B). The epoxy compound (B) is, for example, bisphenol A type epoxy resin, bisphenol F type epoxy resin, hydrogenated bisphenol A type epoxy resin, hydrogenated bisphenol F type epoxy resin, glycidyl ester type epoxy resin, novolac type epoxy resin, urethane modified epoxy resin. Contains at least one compound selected from the group consisting of a resin, a nitrogen-containing epoxy resin obtained by epoxidizing metaxylene di, hydantoin, etc., a rubber-modified epoxy resin containing polybutadiene or NBR (acrylonitrile-butadiene copolymer), and epoxy silane. do. Epoxysilanes include, for example, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylethyldiethoxysilane, and 2-( Contains at least one compound selected from the group consisting of 3,4 epoxycyclohexyl)ethyltrimethoxysilane and the like. Note that the components contained in the epoxy compound (B) are not limited to those listed above.
重合体（Ａ）１００質量部に対するエポキシ化合物（Ｂ）の割合は、例えば０．１質量部以上１０質量部以下であり、１質量部以上５質量部以下であれば好ましく、２質量部以上４質量部以下であれば更に好ましい。 The ratio of the epoxy compound (B) to 100 parts by mass of the polymer (A) is, for example, 0.1 parts by mass or more and 10 parts by mass or less, preferably 1 part by mass or more and 5 parts by mass or less, and 2 parts by mass or more and 4 parts by mass or less. It is more preferable if it is less than parts by mass.
ケチミン化合物（Ｃ）は、上記のとおり、ケチミン構造を有する化合物である。ケチミン化合物は、例えば一級アミノ基を有するアミン化合物とケトン化合物との脱水縮合反応により合成される。 The ketimine compound (C) is a compound having a ketimine structure, as described above. A ketimine compound is synthesized, for example, by a dehydration condensation reaction between an amine compound having a primary amino group and a ketone compound.
ケチミン化合物（Ｃ）はそのままではエポキシ化合物（Ｂ）と反応しにくいが、上述のとおり、ケチミン化合物（Ｃ）は加水分解して一級アミンを生成し、この一級アミンがエポキシ化合物（Ｂ）と反応することで、組成物（Ｘ）が硬化する。このため、組成物（Ｘ）の保管時には組成物（Ｘ）の硬化反応は進行しにくく、そのため、組成物（Ｘ）の一液化が可能である。 Ketimine compound (C) does not easily react with epoxy compound (B) as it is, but as mentioned above, ketimine compound (C) hydrolyzes to produce a primary amine, and this primary amine reacts with epoxy compound (B). By doing so, the composition (X) is cured. Therefore, the curing reaction of composition (X) is difficult to proceed during storage of composition (X), and therefore composition (X) can be made into one liquid.
ケチミン化合物（Ｃ）は、加水分解性シリル基を有するケチミン化合物（Ｃ１）と、加水分解性シリル基を有さないケチミン化合物（Ｃ２）とのうち、少なくとも一方を含有できる。ケチミン化合物（Ｃ）が特に加水分解性シリル基を有するケチミン化合物（Ｃ１）を含有すると、重合体（Ａ）の架橋性シリル基とケチミン化合物（Ｃ１）の架橋性シリル基とが反応して架橋構造を形成できる。そのため、組成物（Ｘ）の硬化性が高くなる。ただし、重合体（Ａ）とケチミン化合物（Ｃ）との間に架橋構造が形成されなくても組成物
（Ｘ）が十分な硬化性を有すれば、ケチミン化合物（Ｃ）は、加水分解性シリル基を有するケチミン化合物（Ｃ１）を必ずしも有しなくてもよい。
The ketimine compound (C) can contain at least one of a ketimine compound (C1) having a hydrolyzable silyl group and a ketimine compound (C2) not having a hydrolyzable silyl group. When the ketimine compound (C) especially contains a ketimine compound (C1) having a hydrolyzable silyl group, the crosslinkable silyl group of the polymer (A) and the crosslinkable silyl group of the ketimine compound (C1) react to cause crosslinking. Can form structures. Therefore, the curability of composition (X) becomes high. However, if the composition (X) has sufficient curability even if a crosslinked structure is not formed between the polymer (A) and the ketimine compound (C), the ketimine compound (C) is hydrolyzable. The ketimine compound (C1) having a silyl group does not necessarily have to be present.
ケチミン化合物（Ｃ１）は、例えば少なくとも一つの架橋性シリル基及び少なくとも一つの一級アミノ基を有するアミン化合物（ｃ１）と、ケトン化合物（ｃ２）との、脱水縮合反応により合成される。アミン化合物（ｃ１）は、例えばＸ－Ｒ”ＮＨ2という構造を
有する。Ｘは架橋性シリル基である。Ｒ”は２価の炭化水素基である。Ｒ”の炭素数は例えば１～１０である。ケトン化合物（ｃ２）は、例えば例えばシクロペンタノン、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、及び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、及びジイソブチルケトン等の脂肪族ケトン；並びにアセトフェノン、ベンゾフェノン、及びプロピオフェノン等の芳香族ケトン等からなる群から選択される少なくとも一種の化合物を含有する。
The ketimine compound (C1) is synthesized, for example, by a dehydration condensation reaction of an amine compound (c1) having at least one crosslinkable silyl group and at least one primary amino group and a ketone compound (c2). The amine compound (c1) has, for example, a structure of X-R''NH 2 .X is a crosslinkable silyl group.R'' is a divalent hydrocarbon group. The number of carbon atoms in R'' is, for example, 1 to 10. Examples of the ketone compound (c2) include cyclic ketones such as cyclopentanone, trimethylcyclopentanone, cyclohexanone, methylcyclohexanone, and trimethylcyclohexanone; acetone, methyl ethyl ketone, and methyl. aliphatic ketones such as propyl ketone, methyl isopropyl ketone, methyl isobutyl ketone, methyl-tert-butyl ketone, diethyl ketone, dipropyl ketone, diisopropyl ketone, dibutyl ketone, and diisobutyl ketone; and acetophenone, benzophenone, and propiophenone. Contains at least one compound selected from the group consisting of aromatic ketones and the like.
ケチミン化合物（Ｃ２）は、例えば２，５，８－トリアザ－１，８－ノナジエン、２，１０－ジメチル－３，６，９－トリアザ－２，９－ウンデカジエン、２，１０－ジフェニル－３，６，９－トリアザ－２，９－ウンデカジエン、３，１１－ジメチル－４，７，１０－トリアザ－３，１０－トリデカジエン、３，１１－ジエチル－４，７，１０－トリアザ－３，１０－トリデカジエン、２，４，１２，１４－テトラメチル－５，８，１１－トリアザ－４，１１－ペンタデカジエン、２，４，２０，２２－テトラメチル－５，１２，１９－トリアザ－４，１９－トリエイコサジエン、２，４，１５，１７－テトラメチル－５，８，１１，１４－テトラアザ－４，１４－オクタデカジエン等からなる群から選択される少なくとも一種の化合物を含有する。なお、ケチミン化合物（Ｃ２）に含まれる成分は前記のみには制限されない。 The ketimine compound (C2) is, for example, 2,5,8-triaza-1,8-nonadiene, 2,10-dimethyl-3,6,9-triaza-2,9-undecadiene, 2,10-diphenyl-3, 6,9-triaza-2,9-undecadiene, 3,11-dimethyl-4,7,10-triaza-3,10-tridecadiene, 3,11-diethyl-4,7,10-triaza-3,10- tridecadiene, 2,4,12,14-tetramethyl-5,8,11-triaza-4,11-pentadecadiene, 2,4,20,22-tetramethyl-5,12,19-triaza-4, Contains at least one compound selected from the group consisting of 19-trieicosadiene, 2,4,15,17-tetramethyl-5,8,11,14-tetraaza-4,14-octadecadiene, etc. . Note that the components contained in the ketimine compound (C2) are not limited to the above.
上述のとおり、エポキシ化合物（Ｂ）のエポキシ基に対するケチミン化合物（Ｃ）のケチミン構造のモル比は、０．４以上０．８以下である。なお、エポキシ化合物（Ｂ）のエポキシ基に対するケチミン化合物（Ｃ）のケチミン構造のモル比とは、エポキシ化合物（Ｂ）のエポキシ基に対する、ケチミン化合物（Ｃ）がすべて加水分解した場合に生じる第一アミンが有する一級アミノ基のモル比であるともいえる。このモル比は０．４５以上０．７５以下であればより好ましく、０．４５以上０．６以下であれば更に好ましい。なお、エポキシ樹脂（Ｂ）が異なる複数種のエポキシ樹脂を含む場合、上述した、エポキシ化合物（Ｂ）のエポキシ基とは、当該複数種のエポキシ樹脂のエポキシ基の総数である。また、ケチミン化合物（Ｃ）が、異なる複数種のケチミン化合物を含む場合、上述したケチミン化合物（Ｃ）のケチミン構造とは、当該複数種のケチミン化合物のケチミン構造の総数である。これらのことから、異なる複数種のエポキシ樹脂及びケチミン化合物を含む場合であっても、エポキシ化合物（Ｂ）のエポキシ基に対するケチミン化合物（Ｃ）のケチミン構造のモル比を算出することが可能である。 As described above, the molar ratio of the ketimine structure of the ketimine compound (C) to the epoxy group of the epoxy compound (B) is 0.4 or more and 0.8 or less. Note that the molar ratio of the ketimine structure of the ketimine compound (C) to the epoxy group of the epoxy compound (B) refers to the molar ratio of the ketimine structure of the ketimine compound (C) to the epoxy group of the epoxy compound (B). It can also be said that it is the molar ratio of primary amino groups that the amine has. This molar ratio is more preferably 0.45 or more and 0.75 or less, and even more preferably 0.45 or more and 0.6 or less. In addition, when the epoxy resin (B) contains multiple types of different epoxy resins, the above-mentioned epoxy groups of the epoxy compound (B) is the total number of epoxy groups of the multiple types of epoxy resins. Further, when the ketimine compound (C) includes a plurality of different types of ketimine compounds, the above-mentioned ketimine structure of the ketimine compound (C) is the total number of ketimine structures of the plurality of types of ketimine compounds. From these facts, even when multiple different types of epoxy resins and ketimine compounds are included, it is possible to calculate the molar ratio of the ketimine structure of the ketimine compound (C) to the epoxy group of the epoxy compound (B). .
組成物（Ｘ）は、更に架橋性シリル基の反応を促進させる触媒を含有してもよい。触媒は、例えば、１，１，３，３－テトラブチル－１，３－ジラウリルオキシカルボニル－ジスタノキサン、ジブチル錫ジラウレート、ジブチル錫オキサイド、ジブチル錫ジアセテート、ジブチル錫フタレートビス（ジブチル錫ラウリン酸）オキサイド、ジブチル錫ビスアセチルアセトナート、ジブチル錫ビス（モノエステルマレート）、オクチル酸錫、ジブチル錫オクトエート、ジブチル錫ジオクトエート、ジオクチル酸オキサイド、アルコキシシリル基を有する錫化合物、スタナスオクトエート、ジブチル錫マレエート、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、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；テトラブチルチタネート、テトラプロピルチタネート、テトラ－ｎ－ブトキシチタネート、テトライソプロポキシ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；並びにジブチルアミン－２－エチルヘキソエート等からなる群から選択される少なくとも一種の化合物を含有する。触媒の割合は、例えば重合体（Ａ）１００質量部に対して０．０１質量部以上１０質量部以下である。
Composition (X) may further contain a catalyst that promotes the reaction of the crosslinkable silyl group. Catalysts include, for example, 1,1,3,3-tetrabutyl-1,3-dilauryloxycarbonyl-distanoxane, dibutyltin dilaurate, dibutyltin oxide, dibutyltin diacetate, dibutyltin phthalate bis(dibutyltin lauric acid) oxide. , dibutyltin bisacetylacetonate, dibutyltin bis(monoester malate), tin octylate, dibutyltin octoate, dibutyltin dioctoate, dioctylic acid oxide, tin compound with alkoxysilyl group, stannath octoate, dibutyltin maleate , dibutyltin bistriethoxysilicate, dibutyltin distearate, dioctyltin dilaurate, dioctyltin diversatate, and organotin compounds such as tin naphthenate; reaction product of dibutyltin oxide and phthalate ester; tetrabutyl titanate, tetrapropyl titanate, tetra -Titanic acid esters such as n-butoxytitanate and tetraisopropoxytitanate; organoaluminum compounds such as aluminum trisacetylacetonate, aluminum trisethylacetoacetate, diisopropoxyaluminum ethylacetoacetate; zirconium tetraacetylacetonate, titanium It contains at least one compound selected from the group consisting of chelate compounds such as tetraacetylacetonate; lead octylate; and dibutylamine-2-ethylhexoate. The proportion of the catalyst is, for example, 0.01 parts by mass or more and 10 parts by mass or less with respect to 100 parts by mass of the polymer (A).
組成物（Ｘ）は可塑剤（Ｄ）を更に含有してもよい。可塑剤（Ｄ）によって、組成物（Ｘ）の粘度が下がりやすく、そのため、組成物（Ｘ）の塗布性が良好になりやすい。さらに、可塑剤（Ｄ）は組成物（Ｘ）の硬化物の柔軟性を高めやすい。 Composition (X) may further contain a plasticizer (D). The plasticizer (D) tends to lower the viscosity of the composition (X), and therefore tends to improve the coating properties of the composition (X). Furthermore, the plasticizer (D) tends to increase the flexibility of the cured product of the composition (X).
可塑剤（Ｄ）は、例えばリン酸エステル、フタル酸エステル、脂肪酸一塩基酸エステル、脂肪酸二塩基酸エステル、ポリアルキレングリコール、脂肪族エステル、エポキシ可塑剤、ポリエステル系可塑剤、ポリエーテル、ポリスチレン、及び（メタ）アクリル重合体からなる群から選択される少なくとも一種の化合物を含有する。 Plasticizers (D) include, for example, phosphoric esters, phthalic esters, fatty acid monobasic esters, fatty acid dibasic esters, polyalkylene glycols, aliphatic esters, epoxy plasticizers, polyester plasticizers, polyethers, polystyrene, and (meth)acrylic polymer.
フタル酸エステルは、例えばフタル酸ジメチル、フタル酸ジエチル、フタル酸ジブチル、フタル酸ジイソブチル、フタル酸ジノルマルヘキシル、フタル酸ビス（２－エチルヘキシル）、フタル酸ジノルマルオクチル、フタル酸ジイソノニル、フタル酸ジノニル、フタル酸ジイソデシル、フタル酸ジイソウンデシル、及びフタル酸ビスブチルベンジル等からなる群から選択される少なくとも一種の化合物を含有する。 Examples of phthalate esters include dimethyl phthalate, diethyl phthalate, dibutyl phthalate, diisobutyl phthalate, di-n-hexyl phthalate, bis(2-ethylhexyl) phthalate, di-n-octyl phthalate, diisononyl phthalate, and dinonyl phthalate. , diisodecyl phthalate, diisoundecyl phthalate, bisbutylbenzyl phthalate, and the like.
ポリアルキレングリコールは、例えばジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、ジプロピレングリコール、トリプロピレングリコール、及びテトラプロピレングリコール等からなる群から選択される少なくとも一種の化合物を含有する。 The polyalkylene glycol contains at least one compound selected from the group consisting of, for example, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, and tetrapropylene glycol.
（メタ）アクリル重合体は、アクリル化合物及びメタクリル化合物のうち少なくとも一種を含む不飽和単量体の重合体である。（メタ）アクリル重合体は、例えば（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、及び（メタ）アクリルアミド等からなる群から選択された少なくとも一種を含む不飽和単量体の重合体である。不飽和単量体は、アクリル化合物及びメタクリル化合物のうち少なくとも一種のみを含んでもよく、これら以外のビニル系単量体等を含有してもよい。 The (meth)acrylic polymer is a polymer of unsaturated monomers containing at least one of an acrylic compound and a methacrylic compound. (Meth)acrylic polymer is an unsaturated monomer containing at least one selected from the group consisting of (meth)acrylic acid, (meth)acrylic acid ester, (meth)acrylonitrile, (meth)acrylamide, etc. It is a polymer. The unsaturated monomer may contain only at least one of acrylic compounds and methacrylic compounds, or may contain vinyl monomers other than these.
可塑剤（Ｄ）は、架橋性シリル基を有してもよく、有していなくてもよい。 The plasticizer (D) may or may not have a crosslinkable silyl group.
可塑剤（Ｄ）は、特に架橋性シリル基を有さず、重量平均分子量が１０００以上５０００以下であるポリプロピレングリコール及び（メタ）アクリル重合体のうち少なくとも一方を含有することが好ましい。この場合、組成物（Ｘ）の低粘度化及び硬化物の柔軟性向上が、より実現しやすい。さらに、可塑剤（Ｄ）は水に溶出しにくくなり、そのため硬化物が水に曝されても硬化物が脆くなりにくい。重量平均分子量が１０００以上であることで可塑剤（Ｄ）が水に特に溶出しにくくなる。また、重量平均分子量が５０００以下であることで、組成物（Ｘ）の低粘度化及び硬化物の柔軟性向上が、更に実現しやすい。この重量平均分子量は１５００以上４０００以下であることがより好ましく、２０００以上３０００以下であれば更に好ましい。なお、重量平均分子量は、ＧＰＣ（ゲル浸透クロマトグラフィー）による測定結果からスチレン換算で得られる値である。 The plasticizer (D) preferably contains at least one of polypropylene glycol and (meth)acrylic polymer, which does not particularly have a crosslinkable silyl group and has a weight average molecular weight of 1000 or more and 5000 or less. In this case, it is easier to reduce the viscosity of the composition (X) and improve the flexibility of the cured product. Furthermore, the plasticizer (D) becomes difficult to dissolve in water, so even if the cured product is exposed to water, the cured product is unlikely to become brittle. When the weight average molecular weight is 1000 or more, the plasticizer (D) is particularly difficult to dissolve in water. Further, when the weight average molecular weight is 5000 or less, it is easier to reduce the viscosity of the composition (X) and improve the flexibility of the cured product. The weight average molecular weight is more preferably 1,500 or more and 4,000 or less, and even more preferably 2,000 or more and 3,000 or less. Note that the weight average molecular weight is a value obtained in terms of styrene from measurement results by GPC (gel permeation chromatography).
重合体（Ａ）１００質量部に対する可塑剤（Ｄ）の割合は、例えば１０質量部以上１０
０質量部以下である。この割合が１０質量部以上であることで組成物（Ｘ）の低粘度化及び硬化物の柔軟性向上が、特に実現しやすい。また、この割合が１００質量部以下であることで、組成物（Ｘ）の良好な硬化性が確保されやすい。
The ratio of the plasticizer (D) to 100 parts by mass of the polymer (A) is, for example, 10 parts by mass or more.
It is 0 parts by mass or less. When this proportion is 10 parts by mass or more, it is particularly easy to reduce the viscosity of the composition (X) and improve the flexibility of the cured product. Further, when this proportion is 100 parts by mass or less, good curability of the composition (X) is easily ensured.
組成物（Ｘ）は充填材を含有してもよい。例えば充填材の量を調整することで、組成物（Ｘ）の流動性を制御でき、そのため例えば組成物（Ｘ）に用途に応じた流動性を付与できる。また充填材が顔料を含有してもよい。その場合、顔料によって組成物（Ｘ）及び硬化物を着色できる。充填材は、例えば重質炭酸カルシウム、軽質炭酸カルシウム、炭酸マグネシウム、含水ケイ酸、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、及びガラスバルーン等からなる群から選択される少なくとも一種の材料を含有する。充填材には分散性改善のため脂肪酸処理や疎水化などの表面処理を行うことが好ましい。 Composition (X) may contain a filler. For example, by adjusting the amount of filler, the fluidity of composition (X) can be controlled, and therefore, for example, fluidity can be imparted to composition (X) depending on the intended use. The filler may also contain a pigment. In that case, the composition (X) and the cured product can be colored with the pigment. The filler is selected from the group consisting of, for example, heavy calcium carbonate, light calcium carbonate, magnesium carbonate, hydrous silicic acid, anhydrous silicic acid, calcium silicate, silica, titanium dioxide, clay, talc, carbon black, and glass balloons. contains at least one material that is It is preferable to subject the filler to surface treatment such as fatty acid treatment or hydrophobization in order to improve dispersibility.
例えば組成物（Ｘ）中の充填材の割合は、重合体（Ａ）１００質量部に対して５０質量部以上５００質量部以下であることが好ましく、１００質量部以上３００質量部以下であれば更に好ましい。 For example, the proportion of the filler in the composition (X) is preferably 50 parts by mass or more and 500 parts by mass or less, and 100 parts by mass or more and 300 parts by mass or less, based on 100 parts by mass of the polymer (A). More preferred.
組成物（Ｘ）は、上記以外の成分を更に含有してもよい。例えば組成物（Ｘ）は、脱水剤、酸化防止剤、タレ防止剤、紫外線吸収剤、光安定剤、溶剤、及び香料等からなる群から選択される少なくとも一種の成分を含有してよい。 Composition (X) may further contain components other than those mentioned above. For example, composition (X) may contain at least one component selected from the group consisting of dehydrating agents, antioxidants, anti-sagging agents, ultraviolet absorbers, light stabilizers, solvents, fragrances, and the like.
特に組成物（Ｘ）が紫外線吸収剤と光安定剤とのうち少なくとも一方を含有すると、組成物（Ｘ）及びその硬化物の耐光性及び耐ＵＶ性が高まりやすい。紫外線吸収剤は、例えばベンゾトリアゾール系紫外線吸収剤、トリアジン系紫外線吸収剤、ベンゾフェノン系紫外線吸収剤、ベンゾエート系紫外線吸収剤等からなる群から選択される少なくとも一種の成分を含有する。光安定剤は、例えばビス（２，２，６，６－テトラメチル－４－ピペリジル）セバケート等のヒンダートアミン系光安定剤を含有する。 In particular, when composition (X) contains at least one of an ultraviolet absorber and a light stabilizer, the light resistance and UV resistance of composition (X) and its cured product tend to increase. The ultraviolet absorber contains at least one component selected from the group consisting of, for example, benzotriazole ultraviolet absorbers, triazine ultraviolet absorbers, benzophenone ultraviolet absorbers, benzoate ultraviolet absorbers, and the like. The light stabilizer includes, for example, a hindered amine light stabilizer such as bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate.
組成物（Ｘ）は、上述のとおり、例えばシーリング材として使用される。この場合、例えば建物の外壁、内壁などにおける目地などに組成物（Ｘ）を充填して放置する。そうすると、上述のとおり、空気中の水分などによって組成物（Ｘ）が硬化する。 Composition (X) is used, for example, as a sealant, as described above. In this case, for example, the composition (X) is filled into joints in the outer wall or inner wall of a building and left. Then, as described above, the composition (X) is cured by moisture in the air.
組成物（Ｘ）は、上述のとおり、例えば接着剤としても使用される。この場合、組成物（Ｘ）は、例えば建材を下地に接着するために使用される。具体的には、例えば下地に組成物（Ｘ）を塗布してから建材を下地に組成物（Ｘ）を介して重ね、この状態で放置する。そうすると、上述のとおり空気中の水分などによって組成物（Ｘ）が硬化する。これにより、建材を下地に接着できる。建材は、例えば外装建築材であり、具体的には例えばタイル、レンガ材、石材、モルタル材又は陶材などである。 Composition (X), as mentioned above, is also used, for example, as an adhesive. In this case, the composition (X) is used, for example, to bond building materials to a base. Specifically, for example, the composition (X) is applied to the base, and then the building material is layered on the base with the composition (X) interposed therebetween, and the composition is left in this state. Then, as described above, the composition (X) is cured by moisture in the air. This allows the building materials to be glued to the base. The building material is, for example, an exterior building material, and specifically, for example, tiles, brick materials, stone materials, mortar materials, or porcelain materials.
本実施形態によると、上述のとおり組成物（Ｘ）の硬化物は良好な柔軟性を有しやすく、かつ水に曝されるなどしても経時的な硬さ及び弾性率の増大が生じにくいため、ひび割れなどの破損が生じにくい。そのため、建物の外装におけるシーリング材や、外装建築材を接着するための接着剤などとして使用しても、良好な耐久性を有することができる。なお、本実施形態に係る組成物（Ｘ）は、外装用途には限られず、建物の内装におけるシーリング材や、内装建築材を接着するための接着剤などとして使用してもよい。組成物（Ｘ）を自動車用途に適用してもよい。また、組成物（Ｘ）の用途は、シーリング材及び接着剤には限られず、例えば緩衝材、被覆材、電子部品などに適用してもよい。 According to the present embodiment, as described above, the cured product of composition (X) tends to have good flexibility, and hardness and elastic modulus are unlikely to increase over time even when exposed to water. Therefore, damage such as cracks is less likely to occur. Therefore, it can have good durability even when used as a sealing material for the exterior of a building or an adhesive for bonding exterior construction materials. Note that the composition (X) according to the present embodiment is not limited to exterior use, and may be used as a sealing material for the interior of a building, an adhesive for bonding interior construction materials, and the like. Composition (X) may also be applied to automotive applications. Further, the use of the composition (X) is not limited to sealing materials and adhesives, and may be applied to, for example, cushioning materials, covering materials, electronic components, etc.
以下、本実施形態の、より具体的な実施例を提示する。なお、本実施形態は、以下の実
施例のみに制限されるものではない。
More specific examples of this embodiment will be presented below. Note that this embodiment is not limited only to the following examples.
１．組成物の調製
表１の「組成」の欄に示す原料を混合して、組成物を調製した。原料の詳細は下記のとおりである。なお、表１に示す原料の配合量は質量部で示され、ケチミン化合物１及びケチミン化合物２については分子内のケチミン構造の総量をｍｍｏｌ部数で換算した値も併記され、エポキシ化合物１、エポキシ化合物２及びエポキシ化合物３については分子内のエポキシ基の総量をｍｍｏｌ部数で換算した値も併記されている。「ケチミン構造/エポキシ基 モル比」は、組成物中のエポキシ化合物の有するエポキシ基に対するケチミン構造のモル比を示す。
－重合体１：ポリオキシアルキレン骨格と架橋性シリル基とを有する重合体、ＡＧＣ社製、品名エクセスター ＥＳ－Ｓ３４３０。
－重合体２：ポリ（メタ）アクリル骨格と架橋性シリル基とを有する重合体（一末端一側鎖ジメトキシシリル基置換ポリ（メタ）アクリル樹脂）、綜研化学社製、開発品番ＮＥ４００３ＤＤ６、重量平均分子量３１０００。
－エポキシ化合物１：ビスフェノールＡ型エポキシ樹脂、ＤＩＣ社製、品名エピクロン８５０、エポキシ当量１８８。
－エポキシ化合物２：エポキシシラン、信越化学工業社製、品番ＫＢＭ４０３、エポキシ当量２３６．３。
－エポキシ化合物３：水添ビスフェノールＡ型エポキシ樹脂、三菱ケミカル社製、品番Ｘ８０００、エポキシ当量２０５。
－ケチミン化合物１：架橋性シリル基を有するケチミン化合物、信越化学工業社製、品番ＫＢＥ９１０３、加水分解後の１級アミン当量３０３ｇ／ｍｏｌ。
－ケチミン化合物２：架橋性シリル基を有さない二価のケチミン化合物、日東化成社製、品番エボニットＫ-１００、加水分解後の１級アミン当量２０９ｇ／ｍｏｌ。
－可塑剤１：ポリプロピレングリコール、ＡＧＣ社製、品名エクセノール３０２０、重量平均分子量３０００。
－可塑剤２：（メタ）アクリル重合体、東亜合成社製、品番ＵＰ１０００、重量平均分子量３０００。
－充填材１：脂肪酸表面処理軽質炭酸カルシウム、白石工業社製、品名ＣＣＲ。
－充填材２：脂肪酸表面処理重質炭酸カルシウム、白石工業社製、品名ホワイトン３０５。
－充填材３：表面処理されていない重質炭酸カルシウム、清水工業社製、品名ＬＷ－３５０。
－触媒：錫触媒、日東化成社製、品番Ｕ２２０Ｈ。
1. Preparation of Composition The raw materials shown in the "Composition" column of Table 1 were mixed to prepare a composition. Details of the raw materials are as follows. The blending amounts of the raw materials shown in Table 1 are shown in parts by mass, and for Ketimine Compound 1 and Ketimine Compound 2, the value calculated by converting the total amount of ketimine structure in the molecule into mmol parts is also shown. For epoxy compound 2 and epoxy compound 3, values obtained by converting the total amount of epoxy groups in the molecule into mmol parts are also listed. The "ketimine structure/epoxy group molar ratio" indicates the molar ratio of the ketimine structure to the epoxy group of the epoxy compound in the composition.
- Polymer 1: Polymer having a polyoxyalkylene skeleton and a crosslinkable silyl group, manufactured by AGC Co., Ltd., product name: EXCESTAR ES-S3430.
- Polymer 2: Polymer having a poly(meth)acrylic skeleton and a crosslinkable silyl group (poly(meth)acrylic resin substituted with a dimethoxysilyl group at one end and one side chain), manufactured by Soken Kagaku Co., Ltd., development product number NE4003DD6, weight average Molecular weight 31,000.
- Epoxy compound 1: Bisphenol A type epoxy resin, manufactured by DIC Corporation, product name Epiclon 850, epoxy equivalent: 188.
- Epoxy compound 2: Epoxy silane, manufactured by Shin-Etsu Chemical Co., Ltd., product number KBM403, epoxy equivalent 236.3.
-Epoxy compound 3: Hydrogenated bisphenol A type epoxy resin, manufactured by Mitsubishi Chemical Corporation, product number X8000, epoxy equivalent weight 205.
- Ketimine compound 1: Ketimine compound having a crosslinkable silyl group, manufactured by Shin-Etsu Chemical Co., Ltd., product number KBE9103, primary amine equivalent after hydrolysis: 303 g/mol.
- Ketimine compound 2: divalent ketimine compound having no crosslinkable silyl group, manufactured by Nitto Kasei Co., Ltd., product number Ebonit K-100, primary amine equivalent after hydrolysis: 209 g/mol.
-Plasticizer 1: Polypropylene glycol, manufactured by AGC, product name Excenol 3020, weight average molecular weight 3000.
-Plasticizer 2: (meth)acrylic polymer, manufactured by Toagosei Co., Ltd., product number UP1000, weight average molecular weight 3000.
- Filler 1: Fatty acid surface-treated light calcium carbonate, manufactured by Shiraishi Kogyo Co., Ltd., product name: CCR.
- Filler 2: Fatty acid surface-treated heavy calcium carbonate, manufactured by Shiraishi Kogyo Co., Ltd., product name Whiten 305.
- Filler 3: Surface-untreated heavy calcium carbonate, manufactured by Shimizu Kogyo Co., Ltd., product name LW-350.
-Catalyst: Tin catalyst, manufactured by Nitto Kasei Co., Ltd., product number U220H.
２．評価試験
２．１．接着強さ
組成物を外装タイルのための接着剤として用いた場合の接着強さを、ＪＩＳ Ａ５５５７：２００６に従って測定した。その結果、破断強度０．４Ｎ／ｍ2以上かつ凝集破壊率
５０％以上の場合を「合格」、破断強度０．４Ｎ／ｍ2未満もしくは凝集破壊率５０％未
満の場合を「不合格」と評価した。
2. Evaluation test 2.1. Adhesive Strength The adhesive strength when the composition was used as an adhesive for exterior tiles was measured according to JIS A5557:2006. As a result, if the breaking strength is 0.4 N/m 2 or more and the cohesive failure rate is 50% or more, it is judged as "pass," and if the breaking strength is less than 0.4 N/m 2 or the cohesive failure rate is less than 50%, it is judged as "fail." evaluated.
表１に示される結果のとおり、実施例１～１１では「合格」の評価が得られたが、ケチミン化合物のケチミン構造のエポキシ基に対するモル比が０．３である比較例１における評価は不合格となった。 As shown in Table 1, Examples 1 to 11 were evaluated as "pass", but Comparative Example 1, in which the molar ratio of the ketimine structure of the ketimine compound to the epoxy group was 0.3, was evaluated as "failed". I passed the exam.
２．２．破断伸び率
組成物から、２ｍｍ厚みのシートを作製し、このシートを２３℃、５０％ＲＨで２８日間養生した後に引張５号ダンベル形状のトムソン刃で打ち抜くことで、サンプルを作製した。このサンプルに対して、引張試験機（島津製作所社製、型番ＡＧＳ－Ｘ）を用いて、１００ｍｍ／ｍｉｎの条件で引張試験を行い、その結果から破断伸び率を求めた。また、サンプルを７０℃の温水に１６８日間浸漬してから、サンプルに対して引張試験を行い、その結果から破断伸び率を求めた。
2.2. Elongation at break A 2 mm thick sheet was prepared from the composition, and after curing this sheet at 23° C. and 50% RH for 28 days, it was punched out with a No. 5 tensile dumbbell-shaped Thomson blade to prepare a sample. This sample was subjected to a tensile test at 100 mm/min using a tensile tester (manufactured by Shimadzu Corporation, model number AGS-X), and the elongation at break was determined from the results. In addition, after immersing the sample in 70° C. hot water for 168 days, a tensile test was performed on the sample, and the elongation at break was determined from the result.
表１に示される結果のとおり、実施例１～１１では初期の破断伸び率は８０％以上であり、１００％以上の評価も実現できた。さらに、初期の破断伸び率と温水浸漬後の破断伸び率との差は２０％ｐｔ以下であり、１０％ｐｔ以下も実現でき、０％ｐｔも実現できた。 As shown in Table 1, in Examples 1 to 11, the initial elongation at break was 80% or more, and an evaluation of 100% or more was also achieved. Furthermore, the difference between the initial elongation at break and the elongation at break after immersion in hot water was 20% pt or less, and it was also possible to achieve 10% pt or less, and even 0% pt.
これに対し、ケチミン化合物のケチミン構造のエポキシ基に対するモル比が０．８５である比較例２～３及び０．９である比較例４では、初期の破断伸び率が８５％以上であったものの、温水浸漬後には破断伸び率が著しく低下した。 On the other hand, in Comparative Examples 2 to 3 where the molar ratio of the ketimine structure of the ketimine compound to the epoxy group was 0.85 and Comparative Example 4 where it was 0.9, the initial elongation at break was 85% or more. , the elongation at break decreased significantly after immersion in hot water.
２．３．５０％モジュラス
組成物から、２ｍｍ厚みのシートを作製し、このシートを２３℃、５０％ＲＨで２８日間養生した後に引張５号ダンベル形状のトムソン刃で打ち抜くことで、サンプルを作製した。このサンプルに対して、引張試験機（島津製作所社製、型番 ＡＧＳ－Ｘ）を用いて、１００ｍｍ／ｍｉｎの条件で引張試験を行い、その結果から伸び率５０％の場合の応力（５０％モジュラス）を求めた。また、サンプルを７０℃の温水に１６８日間浸漬してから、サンプルに対して引張試験を行い、その結果から５０％モジュラスを求めた。
2.3.50% Modulus A 2 mm thick sheet was prepared from the composition, and after curing this sheet at 23°C and 50% RH for 28 days, a sample was prepared by punching it out with a No. 5 tensile dumbbell-shaped Thomson blade. did. This sample was subjected to a tensile test using a tensile testing machine (manufactured by Shimadzu Corporation, model number AGS-X) at a rate of 100 mm/min, and from the results, the stress at an elongation rate of 50% (50% modulus ) was sought. Further, after immersing the sample in 70° C. hot water for 168 days, a tensile test was performed on the sample, and the 50% modulus was determined from the result.
表１に示される結果のとおり、実施例１～１１では初期の５０％モジュラスは０．６ＭＰａ以下であり、０．５ＭＰａ以下及び０．４ＭＰａ以下も実現できた。さらに、初期の５０％モジュラスと温水浸漬後の５０％モジュラスとの差は０．１ＭＰａ以下であり、０ＭＰａも実現できた。 As shown in Table 1, in Examples 1 to 11, the initial 50% modulus was 0.6 MPa or less, and it was also possible to achieve 0.5 MPa or less and 0.4 MPa or less. Furthermore, the difference between the initial 50% modulus and the 50% modulus after immersion in hot water was 0.1 MPa or less, and 0 MPa was also achieved.
これに対し、ケチミン化合物のケチミン構造のエポキシ基に対するモル比が０．８５である比較例２～３及び０．９である比較例４では、初期の５０％モジュラスは０．６ＭＰａ以下であったものの、温水浸漬後には５０％モジュラスは著しく増大した。 On the other hand, in Comparative Examples 2 to 3 where the molar ratio of the ketimine structure of the ketimine compound to the epoxy group was 0.85 and Comparative Example 4 where it was 0.9, the initial 50% modulus was 0.6 MPa or less. However, the 50% modulus increased significantly after hot water immersion.
Claims (6)
エポキシ化合物（Ｂ）と、
ケチミン化合物（Ｃ）とを含み、
前記エポキシ化合物（Ｂ）は、ビスフェノールＡ型エポキシ樹脂、ビスフェノールＦ型エポキシ樹脂、水添ビスフェノールＡ型エポキシ樹脂、水添ビスフェノールＦ型エポキシ樹脂及びエポキシシランからなる群から選択される少なくとも一種の化合物であり、
前記ケチミン化合物（Ｃ）は、加水分解性シリル基を有するケチミン化合物（Ｃ１）を含有し、
前記重合体（Ａ）１００質量部に対する前記エポキシ化合物（Ｂ）の割合は、２質量部以上４質量部以下であり、
前記エポキシ化合物（Ｂ）の有するエポキシ基に対する、前記ケチミン化合物（Ｃ）の有するケチミン構造のモル比が、０．４５以上０．６以下である、
硬化性組成物。 A polymer (A) having a crosslinkable silyl group,
An epoxy compound (B),
ketimine compound (C);
The epoxy compound (B) is at least one compound selected from the group consisting of bisphenol A epoxy resin, bisphenol F epoxy resin, hydrogenated bisphenol A epoxy resin, hydrogenated bisphenol F epoxy resin, and epoxy silane. can be,
The ketimine compound (C) contains a ketimine compound (C1) having a hydrolyzable silyl group,
The ratio of the epoxy compound (B) to 100 parts by mass of the polymer (A) is 2 parts by mass or more and 4 parts by mass or less,
The molar ratio of the ketimine structure possessed by the ketimine compound (C) to the epoxy group possessed by the epoxy compound (B) is 0.45 or more and 0.6 or less;
Curable composition.
請求項１に記載の硬化性組成物。 The polymer (A) contains a component having at least one of a polyoxyalkylene skeleton and a poly(meth)acrylate skeleton,
The curable composition according to claim 1.
請求項１又は２に記載の硬化性組成物。 further containing a plasticizer (D);
The curable composition according to claim 1 or 2.
請求項３に記載の硬化性組成物。 The plasticizer (D) does not have a crosslinkable silyl group and contains at least one of polypropylene glycol and (meth)acrylic polymer having a weight average molecular weight of 1000 to 5000.
The curable composition according to claim 3.
請求項１から４のいずれか一項に記載の硬化性組成物。 Used as a sealant,
The curable composition according to any one of claims 1 to 4.
請求項１から４のいずれか一項に記載の硬化性組成物。 used as adhesive,
The curable composition according to any one of claims 1 to 4.
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