JP5898781B2 - 末端変性ポリブタジエン又は末端変性水素添加ポリブタジエンの製造方法及びそれらを含有する組成物 - Google Patents
末端変性ポリブタジエン又は末端変性水素添加ポリブタジエンの製造方法及びそれらを含有する組成物 Download PDFInfo
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- JP5898781B2 JP5898781B2 JP2014541940A JP2014541940A JP5898781B2 JP 5898781 B2 JP5898781 B2 JP 5898781B2 JP 2014541940 A JP2014541940 A JP 2014541940A JP 2014541940 A JP2014541940 A JP 2014541940A JP 5898781 B2 JP5898781 B2 JP 5898781B2
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- terminal
- polybutadiene
- substituent
- alkyl group
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- 229920002857 polybutadiene Polymers 0.000 title claims description 121
- 239000005062 Polybutadiene Substances 0.000 title claims description 119
- 239000000203 mixture Substances 0.000 title claims description 68
- 238000000034 method Methods 0.000 title description 18
- -1 diisocyanate compound Chemical class 0.000 claims description 181
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 52
- 125000001424 substituent group Chemical group 0.000 claims description 51
- 229920000642 polymer Polymers 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 49
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 38
- 238000004519 manufacturing process Methods 0.000 claims description 36
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 29
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 28
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 26
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 229910052782 aluminium Inorganic materials 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000000732 arylene group Chemical group 0.000 claims description 13
- 125000005549 heteroarylene group Chemical group 0.000 claims description 13
- 230000000379 polymerizing effect Effects 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 7
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000003752 zinc compounds Chemical class 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 25
- 229920005989 resin Polymers 0.000 description 20
- 239000011347 resin Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 18
- 229920001296 polysiloxane Polymers 0.000 description 16
- 239000013522 chelant Substances 0.000 description 14
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 14
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 13
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 13
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- 239000000049 pigment Substances 0.000 description 11
- 229920000647 polyepoxide Polymers 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 125000005442 diisocyanate group Chemical group 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 229920003986 novolac Polymers 0.000 description 7
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- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000008393 encapsulating agent Substances 0.000 description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
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- 238000010438 heat treatment Methods 0.000 description 6
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 239000012975 dibutyltin dilaurate Substances 0.000 description 5
- 239000007870 radical polymerization initiator Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 125000004980 cyclopropylene group Chemical group 0.000 description 4
- 230000001678 irradiating effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- 102100033617 Retinal-specific phospholipid-transporting ATPase ABCA4 Human genes 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002216 antistatic agent Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000004956 cyclohexylene group Chemical group 0.000 description 3
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- VNTDZUDTQCZFKN-UHFFFAOYSA-L zinc 2,2-dimethyloctanoate Chemical compound [Zn++].CCCCCCC(C)(C)C([O-])=O.CCCCCCC(C)(C)C([O-])=O VNTDZUDTQCZFKN-UHFFFAOYSA-L 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 2
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
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- 239000005995 Aluminium silicate Substances 0.000 description 2
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
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- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003918 triazines Chemical class 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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000000015 trinitrotoluene Substances 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- PTCSYKMYHDPUDF-UHFFFAOYSA-N zinc acetyl acetate Chemical compound [Zn+2].C(C)(=O)OC(C)=O PTCSYKMYHDPUDF-UHFFFAOYSA-N 0.000 description 1
- 229940098697 zinc laurate Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- GPYYEEJOMCKTPR-UHFFFAOYSA-L zinc;dodecanoate Chemical compound [Zn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O GPYYEEJOMCKTPR-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
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Description
本願は、2012年10月16日に出願された日本国特許出願第2012−228989号に対し優先権を主張し、その内容をここに援用する。
(1)式(I)
式(II)
式(III)
有機アルミニウム化合物及び有機亜鉛化合物(ただし、ナフテン酸亜鉛は除く)から選ばれる少なくとも1種の存在下で反応させることを特徴とする、式(IV)
(2)式(V)
有機アルミニウム化合物及び有機亜鉛化合物(ただし、ナフテン酸亜鉛は除く)から選ばれる少なくとも1種の存在下で反応させることを特徴とする、式(IV)
(3)有機アルミニウム化合物が、式(VI)
(4)有機亜鉛化合物が、式(VII)
また、本発明は、
(5)式(IV)
(6)式(IV)で表される末端アクリル変性ポリブタジエン又は末端アクリル変性水素添加ポリブタジエン100重量部に対し、有機アルミニウム化合物及び有機亜鉛化合物(ただし、ナフテン酸亜鉛は除く)から選ばれる少なくとも1種を0.001重量部〜10重量部含有することを特徴とする(5)に記載の末端変性ポリブタジエン又は末端変性水素添加ポリブタジエン組成物に関する。
「直鎖又は分岐鎖を有するC1〜C10のアルキレン基とC1〜C6のアルキル基を置換基として有していても良いC3〜C8のシクロアルキレン基とが結合した基」、
「直鎖又は分岐鎖を有するC1〜C10のアルキレン基とハロゲン原子、C1〜C6アルキル基又はC1〜C6アルコキシ基を置換基として有していても良いアリーレン基とが結合した基」、
「直鎖又は分岐鎖を有するC1〜C10のアルキレン基とハロゲン原子、C1〜C6アルキル基又はC1〜C6アルコキシ基を置換基として有していても良いヘテロアリーレン基とが結合した基」等を意味する。
(末端変性ポリブタジエン又は末端変性水素添加ポリブタジエン)
本発明の末端変性ポリブタジエン又は末端変性水素添加ポリブタジエンは、以下の式(IV)で表されるものをいう。
(製造方法)
本発明の末端変性ポリブタジエン又は末端変性水素添加ポリブタジエンは、下記に示す方法に従って製造することができる。
(末端変性ポリブタジエン又は末端変性水素添加ポリブタジエン組成物)
本発明において、「末端変性ポリブタジエン又は末端変性水素添加ポリブタジエン組成物」とは、式(IV)
(硬化性組成物及び硬化物)
本発明の末端変性ポリブタジエン又は末端変性水素添加ポリブタジエン組成物に、さらに、他の成分を添加することにより、硬化性組成物として用いることができる。
(末端変性水素添加ポリブタジエン組成物(以下、単に「組成物」という)の製造)
[実施例1](組成物A−1の製造)
十分に乾燥した空気で反応フラスコを置換した。これに、ヒドロキシエチルアクリレート30.2gが入った滴下ロート、冷却管、温度計を取り付けた後、反応フラスコにイソホロンジイソシアネート63.4gを加え、内温27.5℃にて、ヒドロキシエチルアクリレートの滴下を開始した。0.5時間後、滴下を完了し、内温60℃〜80℃の範囲で2時間撹拌した。得られた化合物を以下、HA−1と略す。
[実施例2](組成物B−1の製造)
アルミキレートM(川研ファインケミカル社製)に変えて、ネオデカン酸亜鉛(ABCR社製)2.6gを用いた以外は実施例1と同様に行い、組成物B−1を得た。
[比較例1](組成物C−1の製造)
アルミキレートM(川研ファインケミカル社製)に変えて、ナフテン酸亜鉛(添川理化学社製)2.6gを用いた以外は実施例1と同様に行い、組成物C−1を得た。
[比較例2](組成物D−1の製造)
アルミキレートM(川研ファインケミカル社製)に変えて、ナフテン酸亜鉛(添川理化学社製)4.0gを用いた以外は実施例1と同様に行い、組成物D−1を得た。
[比較例3](組成物E−1の製造)
アルミキレートM(川研ファインケミカル社製)に変えて、ジオクチルスズジラウレート(日東化成社製)0.16gを用いた以外は実施例1と同様に行い、組成物E−1を得た。
[比較例4](組成物F−1の製造)
アルミキレートM(川研ファインケミカル社製)に変えて、ジオクチルスズジラウレート(日東化成社製)0.22gを用いた以外は実施例1と同様に行い、組成物F−1を得た
[実施例3](組成物A−2の製造)
十分に乾燥した空気で反応フラスコを置換した。これに、ヒドロキシエチルアクリレート139.7gが入った滴下ロート、冷却管、温度計を取り付けた後、反応フラスコにトリレンジイソシアネート(2−メチル−1,3−ベンゼンジイソシアネートと4−メチル−1,3−ベンゼンジイソシアネートの混合物)220.01gを加え、乾燥空気気流下、内温31.4℃にて、ヒドロキシエチルアクリレートの滴下を開始した。1.5時間後、滴下を完了し、内温60℃〜80℃の範囲で1時間撹拌した。得られた化合物を以下、HA−2と略す。
[実施例4](組成物B−2の製造)
アルミキレートM(川研ファインケミカル社製)に変えて、ネオデカン酸亜鉛(ABCR社製)1.8gを用いた以外は実施例3と同様に行い、組成物B−2を得た。
[比較例5](組成物C−2の製造)
アルミキレートM(川研ファインケミカル社製)に変えて、ネオデカン酸バリウム(ABCR社製)0.95gを用いた以外は実施例3と同様に行い、組成物C−2を得た。
[比較例6](組成物D−2の製造)
アルミキレートM(川研ファインケミカル社製)に変えて、n−ブチル燐酸エステルチタン(日本曹達社製)0.42gを用いた以外は実施例3と同様に行い、組成物D−2を得た。
[比較例7](組成物E−2の製造)
アルミキレートM(川研ファインケミカル社製)に変えて、n−ブチル燐酸エステルチタン(日本曹達社製)0.84gを用いた以外は実施例3と同様に行い、組成物E−2を得た。
[比較例8](組成物F−2の製造)
アルミキレートM(川研ファインケミカル社製)に変えて、ジブチルスズジラウレート(日東化成社製)0.19gを用いた以外は実施例3と同様に行い、組成物F−2を得た。
(外観試験)
200mLサンプル瓶に、組成物A−1〜F−1および組成物A−2〜F−2をそれぞれ155g以上入れて脱泡した。外観を白濁(濁り)、透明、着色の点で評価した。結果を表1に表す。
(粘度測定)
組成物A−1〜F−1および組成物A−2〜F−2の粘度を、E型粘度計(東機産業(株)製TVE−22)を使用し、45℃にて測定した。結果を表2に表す。
サンプル瓶に、組成物A−1、B−1、D−1、E−1、F−1をそれぞれ10〜30g入れて、80℃のオーブンにて保存した。1、2、4、8週後、それぞれサンプルを取り出して粘度を測定した。E型粘度の測定結果を図1に表し、経時変化率を図2に表す。
Claims (5)
- 式(I)
式(II)
式(III)
- 式(V)
- アルミニウムアルコキシドが、式(VI)
- 式(IV)
- 式(IV)で表される末端アクリル変性ポリブタジエン又は末端アクリル変性水素添加ポリブタジエン100重量部に対し、アルミニウムアルコキシド及び有機亜鉛化合物から選ばれる少なくとも1種を0.001重量部〜10重量部含有することを特徴とする請求項4に記載の末端変性ポリブタジエン又は末端変性水素添加ポリブタジエン組成物。
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CN104781288A (zh) | 2015-07-15 |
KR101717913B1 (ko) | 2017-03-20 |
TWI504622B (zh) | 2015-10-21 |
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US9815922B2 (en) | 2017-11-14 |
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EP2910578A1 (en) | 2015-08-26 |
EP2910578A4 (en) | 2016-06-29 |
TW201428015A (zh) | 2014-07-16 |
US20150240009A1 (en) | 2015-08-27 |
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