JP5507698B2 - 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の製造方法及びそれらを含有する組成物 - Google Patents
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の製造方法及びそれらを含有する組成物 Download PDFInfo
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- JP5507698B2 JP5507698B2 JP2012534928A JP2012534928A JP5507698B2 JP 5507698 B2 JP5507698 B2 JP 5507698B2 JP 2012534928 A JP2012534928 A JP 2012534928A JP 2012534928 A JP2012534928 A JP 2012534928A JP 5507698 B2 JP5507698 B2 JP 5507698B2
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- polybutadiene
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- compound
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- 229920002857 polybutadiene Polymers 0.000 title claims description 120
- 239000005062 Polybutadiene Substances 0.000 title claims description 118
- 239000000203 mixture Substances 0.000 title claims description 77
- 238000000034 method Methods 0.000 title claims description 20
- -1 diisocyanate compound Chemical class 0.000 claims description 194
- 125000001424 substituent group Chemical group 0.000 claims description 54
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 52
- 229920000642 polymer Polymers 0.000 claims description 49
- 238000004519 manufacturing process Methods 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 45
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 38
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 34
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 30
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 27
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims description 25
- 150000001622 bismuth compounds Chemical class 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000000732 arylene group Chemical group 0.000 claims description 14
- 230000000379 polymerizing effect Effects 0.000 claims description 14
- 125000005549 heteroarylene group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 7
- 125000003837 (C1-C20) alkyl group Chemical group 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 35
- MWXWNYHYPMRCHN-UHFFFAOYSA-N [Bi].C(C)C(C(=O)O)CCCC.C(C)C(C(=O)O)CCCC.C(C)C(C(=O)O)CCCC Chemical compound [Bi].C(C)C(C(=O)O)CCCC.C(C)C(C(=O)O)CCCC.C(C)C(C(=O)O)CCCC MWXWNYHYPMRCHN-UHFFFAOYSA-N 0.000 description 21
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 20
- 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
- 230000000052 comparative effect Effects 0.000 description 14
- 239000003822 epoxy resin Substances 0.000 description 11
- 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 125000005442 diisocyanate group Chemical group 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 7
- 229920003986 novolac Polymers 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229910052797 bismuth Inorganic materials 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000010936 titanium Substances 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- 239000000463 material Substances 0.000 description 5
- 239000007870 radical polymerization initiator Substances 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- 0 CC*C1CC=CC1 Chemical compound CC*C1CC=CC1 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
- 239000007983 Tris buffer Substances 0.000 description 4
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical group [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 230000001678 irradiating effect Effects 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
- 238000003860 storage Methods 0.000 description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 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
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-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
- 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
- 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
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 3
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 239000008393 encapsulating agent Substances 0.000 description 3
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-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
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 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 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
- 125000000962 organic group Chemical group 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000003566 sealing material Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 150000003606 tin compounds Chemical class 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical group 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
- 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
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 2
- TYMSARXTOPEHBY-UHFFFAOYSA-N CCCCCCCCCCCCCO[Zr] Chemical compound CCCCCCCCCCCCCO[Zr] TYMSARXTOPEHBY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000004641 Diallyl-phthalate Substances 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- 229920003235 aromatic polyamide Polymers 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 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
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-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
- 238000010894 electron beam technology Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 229940093858 ethyl acetoacetate Drugs 0.000 description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 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 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000005865 ionizing radiation Effects 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000006606 n-butoxy group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 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 2
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
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- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- DVQHRBFGRZHMSR-UHFFFAOYSA-N sodium methyl 2,2-dimethyl-4,6-dioxo-5-(N-prop-2-enoxy-C-propylcarbonimidoyl)cyclohexane-1-carboxylate Chemical compound [Na+].C=CCON=C(CCC)[C-]1C(=O)CC(C)(C)C(C(=O)OC)C1=O DVQHRBFGRZHMSR-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- 238000013112 stability test Methods 0.000 description 1
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- 235000007586 terpenes Nutrition 0.000 description 1
- MVQLEZWPIWKLBY-UHFFFAOYSA-N tert-butyl 2-benzoylbenzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 MVQLEZWPIWKLBY-UHFFFAOYSA-N 0.000 description 1
- WKEWCYHGACEYTR-UHFFFAOYSA-N tert-butyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(C)(C)C WKEWCYHGACEYTR-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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- 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
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- 150000003609 titanium compounds Chemical class 0.000 description 1
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- KNPRLIQQQKEOJN-UHFFFAOYSA-N tri(propan-2-yloxy)bismuthane Chemical compound [Bi+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] KNPRLIQQQKEOJN-UHFFFAOYSA-N 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
- PCOBHRURWGDXGK-UHFFFAOYSA-N tripropoxybismuthane Chemical compound CCCO[Bi](OCCC)OCCC PCOBHRURWGDXGK-UHFFFAOYSA-N 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
- CUYORGNTEMJARP-UHFFFAOYSA-N tris[(1-methoxy-2-methylpropan-2-yl)oxy]bismuthane Chemical compound COCC(C)(C)O[Bi](OC(C)(C)COC)OC(C)(C)COC CUYORGNTEMJARP-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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
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Description
(1)式(I)
式(II)
式(III)
有機ビスマス化合物及びテトラアルコキシジルコニウム化合物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)
有機ビスマス化合物及びテトラアルコキシジルコニウム化合物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(VII)
本発明の製造方法で得られる生成物(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と、有機ビスマス化合物又はテトラアルコキシジルコニウム化合物の混合物)は、白濁を生じなかった。
また、無色透明なウレタン化合物を得るための必要化学量は有機ビスマス化合物の方が少なくて済み、触媒能は有機ビスマス化合物の方が優れていた。
さらに、驚くべきことに、有機スズ化合物を用いて製造した生成物は、時間の経過とともに粘度が上昇していくのに対し、本発明の製造方法で得られた生成物は、経時による粘度変化が少なく、保存安定性が優れていた。
「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」の「C1〜C6アルキル基」としては、上記「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」の「C1〜C6アルキル基」と同様の基を挙げることができる。
「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」の「C1〜C6アルコキシ基」としては、メトキシ基、エトキシ基、n−プロポキシ基、イソプロポキシ基、n−ブトキシ基、1−メチル−n−プロポキシ基、2−メチル−n−プロポキシ基、t−ブトキシ基、n−ペンチルオキシ基、1−メチル−n−ブトキシ基、2−メチル−n−ブトキシ基、3−メチル−n−ブトキシ基、1,1−ジメチル−n−プロポキシ基、2,2−ジメチル−n−プロポキシ基、1,2−ジメチル−n−プロポキシ基、1−エチル−n−プロポキシ基、n−ヘキシルオキシ基、1−メチル−n−ペンチルオキシ基、2−メチル−n−ペンチルオキシ基、3−メチル−n−ペンチルオキシ基、4−メチル−n−ペンチルオキシ基、1,1−ジメチル−n−ブトキシ基、2,2−ジメチル−n−ブトキシ基、3,3−ジメチル−n−ブトキシ基、1,2−ジメチル−n−ブトキシ基、1,3−ジメチル−n−ブトキシ基、2,3−ジメチル−n−ブトキシ基、1−エチル−n−ブトキシ基、2−エチル−n−ブトキシ基、1−(イソプロピル)−n−プロポキシ基等を挙げることができる。
「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。
「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」としては、メチレン−ピリジン−2,3−ジイル基、メチレン−ピラジン−2,5−ジイル基、メチレン−ピリミジン−2,4−ジイル基等が挙げられる。また、これらの順序が入れ替わった基でもよい。
本発明の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は、以下の式(IV)、式(VII)又は(X)で表されるものをいう。
また、式(XI)で表される1,4−結合繰り返し単位が、二重結合を有する場合には、トランス体、シス体、又はそれらの混合体が存在しうる。
本発明の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は、下記に示す方法に従って製造することができる。
上記例示において、(メタ)アクリレートはアクリレート又はメタアクリレートを意味する。以下も同様である。
上記アクリレート又メタアクリレート化合物の使用量は、重合体末端にヒドロキシル基を有するポリブタジエン又は水素添加ポリブタジエンのヒドロキシル基に対して、0.2〜2倍モルの範囲である。
反応温度は、通常0℃〜100℃、好ましくは室温〜80℃の範囲であり、反応は通常数分〜数時間で完結する。
本発明において、「末端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組成物」とは、式(X)
本発明の末端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。
そのような硬化性組成物は、目的に応じて、添加した他の成分と共に、加熱、光、ラジカル重合開始剤等により硬化することができる。あるいは、マイケル付加法によっても硬化できる。
加熱する方法としては、特に限定されず、ヒーター等の従来公知の加熱方法を用いることができる。
光は、例えば、紫外線、可視光、X線、電子線等を用いることが出来るが、紫外線を用いることが好ましい。紫外線はエネルギーが高いため、紫外線を硬化性組成物に照射することにより硬化反応を促進することが出来、硬化性組成物の硬化速度を速めることが出来ると共に、硬化物における未反応の硬化性組成物の量を低減することが出来る。
硬化状態は、フーリエ変換赤外分光分析装置や光化学反応熱量計等を用いて測定することが出来るので、硬化物が完全に硬化するための硬化条件(光の照射時間、光強度等、加熱温度、加熱時間等)を適宜選定することが出来る。
重合性ビニル化合物としては、スチレン、ビニルトルエン、α−メチルスチレン、ジビニルベンゼンなどの芳香族ビニル化合物;(メタ)アクリル酸メチル、(メタ)アクリル酸2−ヒドロキシエチル、(メタ)アクリル酸t−ブチル、(メタ)アクリル酸n−ヘキシル、(メタ)アクリル酸イソブチル、(メタ)アクリル酸シクロヘキシル、(メタ)アクリル酸2−エチルヘキシル、(メタ)アクリル酸ラウリル、(メタ)アクリル酸ステアリル、(メタ)アクリル酸ベンジル、(ポリ)エチレングリコールのモノあるいはジ(メタ)アクリレート、(ポリ)プロピレングリコールのモノあるいはジ(メタ)アクリレート、1,4−ブタンジオールのモノ−あるいはジ−(メタ)アクリレート、トリメチロールプロパンのモノ−、ジ−あるいはトリ−(メタ)アクリレートなどの不飽和カルボン酸エステル類;ジアリルフタレート、ジアリルアクリルアミド、トリアリル(イソ)シアヌレート、トリアリルトリメリテート、o,o’−ジアリルビスフェノールA、o,o’−ジアリルビスフェノールF、1,1,1,3,3,3−ヘキサフルオロ−2,2−ビス(p−ヒドロキシ−o−アリルフェニル)プロパン、アリル化フェノールノボラック、1,1,3−トリス−(4−ヒドロキシフェニル)プロパン、1,1,2,2−テトラ(4−ヒドロキシフェニル)エタン、フェノール類とヒドロキシベンズアルデヒドとの脱水縮合物等のアリル化物;(ポリ)エチレングリコールジ(メタ)アクリレート、(ポリ)プロピレングリコールジ(メタ)アクリレートなどの(ポリ)オキシアルキレングリコールジ(メタ)アクリレート;TEA−1000,TE−1000,TEAI−1000(日本曹達製)などの末端アクリル変性ポリブタジエンなどが挙げられる。また、ブタジエン、イソプレン、クロロプレンなどの共役ジエン化合物、アクリル酸、メタクリル酸、イタコン酸、フマル酸、グリシジルメタクリレート、ビニルピリジン、ジエチルアミノエチルアクリレート、N−メチルメタクリルアミド、アクリロニトリルなどの反応性官能基含有化合物が挙げられる。これらの重合性ビニル化合物は、1種単独でも、2種以上の混合物でも使用することができる。
熱可塑性樹脂として、芳香族又は脂肪族系の石油樹脂、ロジン樹脂、テルペン樹脂、クマロン樹脂、キシレン樹脂、ケトン樹脂等を使用することができる。
光硬化性樹脂としては、アクリル系化合物を主成分とする紫外線硬化性樹脂、ウレタンアクリレートオリゴマーまたはポリエステルウレタンアクリレートオリゴマーを主成分とする紫外線硬化性樹脂、エポキシ系樹脂、ビニルフェノール系樹脂等を使用することができる。
カップリング剤として、一般式 XSi3Y3(式中、Xはビニル基、メタクリロキシプロピル基、アミノアルキル基、メルカプトアルキル基、エポキシアルキル基等の非加水分解型の有機基、Yはハロゲン、アルコキシ基等の加水分解型の有機基を示す)で表されるシラン化合物、例えば、γ−グリシドキシプロピルトリメトキシシラン、α−アミノプロピルトリエトキシシラン等のシランカップリング剤、前記一般式中のSiをTiに置き換えたチタンカップリング剤を使用できる。
本発明の硬化物は、重合体が末端変性水素添加ポリブタジエンである場合、黄色く黄変せず、透過率が向上し、光学材料に最適な材料になる。
十分に乾燥した空気(シリカゲルで乾燥)で反応フラスコを置換した。これに、トルエンジイソシアネート15.83gが入った滴下ロート、冷却管、温度計を取り付けた後、反応フラスコにヒドロキシエチルアクリレート(以下、β−HEAと略す)27.34g、末端アルコール水素添加ポリブタジエン(GI−1000:日本曹達(株)社製)157.5g、トリス(2−エチルヘキサン酸ビスマス(2−エチルへキサン酸を42%〜45%含有する)0.20g、及び、ビス−2,6−t−ブチル−4−ヒドロキシトルエン(以下、BHTと略す)0.11gを加えて攪拌した。乾燥空気気流下、室温にて、トルエンジイソシアネートを12分かけて滴下した。滴下終了後、内温60℃〜68℃に昇温して熟成し、残NCO(%)が0.1%未満になったら、反応終了と判断し、末端変性水素添加ポリブタジエンを得た。
十分に乾燥した空気(シリカゲルで乾燥)で反応フラスコを置換した。これに、β−HEA95.95gが入った滴下ロート、冷却管、温度計を取り付けた後、反応フラスコにトルエンジイソシアネート150gを加え、乾燥空気気流下、内温68℃にて、β−HEAの滴下を開始した。1.5時間後、滴下を完了し、内温60℃〜68℃の範囲で1時間熟成した。熟成後の、残NCO(%)は、15.5%(±0.5%)であった。得られた化合物を以下、HEAアダクトと略す。
トリス(2−エチルヘキサン酸)ビスマスの添加量を0.15gに変えた以外は実施例2と同様に行い、組成物Bを得た。
トリス(2−エチルヘキサン酸)ビスマスの添加量を0.13に変えた以外は実施例2と同様に行い、組成物Cを得た。
トリス(2−エチルヘキサン酸)ビスマスを、テトラ−n−プロポキシジルコニウム(1−プロパノールを23〜28%含有する)(日本曹達(株)製、以下TPZRと略す)0.20gに変えた以外は実施例2と同様に行い、組成物Dを得た。
トリス(2−エチルヘキサン酸)ビスマスを、テトラ−n−ブトキシジルコニウム(1−ブタノールを15%含有する)(日本曹達(株)製、以下TBZRと略す)0.20gに変えた以外は実施例2と同様に行い、組成物Eを得た。
トリス(2−エチルヘキサン酸)ビスマスを、オクトキシ,トリデコキシ−ジルコニウム(1−ブタノールを2〜4%含有する)(日本曹達(株)製、以下ZR−151と略す)0.20gに変えた以外は実施例2と同様に行い、組成物Fを得た。
トリス(2−エチルヘキサン酸)ビスマスを、ZR−151 0.30gに変えた以外は実施例2と同様に行い、組成物Gを得た。
トリス(2−エチルヘキサン酸)ビスマスを、モノブトキシジルコニウム(IV)トリ−i−ステアレート(1−ブタノールを<5%含有する)(日本曹達(株)製、以下ZR−152と略す)0.19gに変えた以外は実施例2と同様に行い、組成物Hを得た。
トリス(2−エチルヘキサン酸)ビスマスを、ジブトキシジルコニウムビス(エチルアセトアセテート)(1−ブタノールを25〜35%含有する)(松本ファインケミカル(株)製、以下ZC−580と略す)0.20gに変えた以外は実施例2と同様に行い、組成物Iを得た。
トリス(2−エチルヘキサン酸)ビスマスを、テトラブトキシジルコニウムとアセチルアセトンとの反応物(1−ブタノールを24%含有する)(日本曹達(株)製、以下ZAAと略す)0.20gに変えた以外は実施例2と同様に行い、組成物Jを得た。
トリス(2−エチルヘキサン酸)ビスマスを、ナフテン酸亜鉛(添川理化学(株)製)1.9g(含有量10%)に変えた以外は実施例2と同様に行い、組成物Kを得た。
トリス(2−エチルヘキサン酸)ビスマスを、トリオクタン酸鉄(添川理化学(株)製)3.18g(含有量6%)に変えた以外は実施例2と同様に行い、組成物Lを得た。
トリス(2−エチルヘキサン酸)ビスマスを、テトラn−ブトキシチタン重合体;Ti含有量23.6%(日本曹達(株)製、以下B−1と略す)0.20gに変えた以外は実施例2と同様に行い、組成物Mを得た。
トリス(2−エチルヘキサン酸)ビスマスを、テトラn−ブトキシチタン重合体; Ti含有量31.5%(1−ブタノールを<5%含有する)(日本曹達(株)製、以下B−4と略す)0.22gに変えた以外は実施例2と同様に行い、組成物Nを得た。
トリス(2−エチルヘキサン酸)ビスマスを、テトラn−ブトキシチタン重合体; Ti含有量34.5%(1−ブタノールを<5%含有する)(日本曹達(株)製、以下B−10と略す)0.21gに変えた以外は実施例2と同様に行い、組成物Oを得た。
トリス(2−エチルヘキサン酸)ビスマスを、テトラi−プロポキシチタン重合体; Ti含有量28.2%(日本曹達(株)製、以下A−1と略す)0.21gに変えた以外は実施例2と同様に行い、組成物Pを得た。
トリス(2−エチルヘキサン酸)ビスマスを、Reaction products with tetrapropoxy titanium and pivalic acid(2−プロパノールを24〜25%含有する)(日本曹達(株)製、以下TPAと略す)0.21gに変えた以外は実施例2と同様に行い、組成物Qを得た。
トリス(2−エチルヘキサン酸)ビスマスを、プロパンジオキシチタンビス(エチルアセトアセテート)(2−プロパノールを40%含有する)(日本曹達(株)製、以下T−60と略す)0.20gに変えた以外は実施例2と同様に行い、組成物Rを得た。
トリス(2−エチルヘキサン酸)ビスマスを、ジブチルスズジラウレート0.20gに変えた以外は実施例2と同様に行い、組成物Sを得た。
トリス(2−エチルヘキサン酸)ビスマスを、ジブチルスズジラウレート0.08gに変えた以外は実施例2と同様に行い、組成物Tを得た。
トリス(2−エチルヘキサン酸)ビスマスを加えない以外は実施例2と同様に行い、化合物Uを得た。
200mLサンプル瓶に、組成物A〜Tおよび化合物U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。
組成物A〜Tおよび化合物U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1に表す。
サンプル瓶に、組成物A、B、D、G、Sをそれぞれ20g入れて、80℃のオーブンにて保存した。1週おきにサンプルを取り出して粘度を測定した。結果を図1に表す。
サンプル瓶に、組成物A、B、D、G、Sをそれぞれ20g入れて、80℃のオーブンにて保存した。3月後、6月後、12月後にそれぞれサンプルを取り出して粘度を測定した。結果を図2に表す。
Claims (6)
- 式(I)
式(II)
式(III)
有機ビスマス化合物及びテトラアルコキシジルコニウム化合物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)
- 式(V)
有機ビスマス化合物及びテトラアルコキシジルコニウム化合物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(VII)
- 式(X)
- 式(X)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、有機ビスマス化合物及びテトラアルコキシジルコニウム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5に記載の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組成物。
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10414834B2 (en) | 2014-12-25 | 2019-09-17 | Kuraray Co., Ltd. | Modified liquid diene rubber and resin composition containing modified liquid diene rubber |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5824884B2 (ja) * | 2011-06-06 | 2015-12-02 | 三菱レイヨン株式会社 | ウレタン(メタ)アクリレートの製造方法 |
TWI504622B (zh) * | 2012-10-16 | 2015-10-21 | Nippon Soda Co | A method for producing a polybutadiene or a terminal modified hydrogenated polybutadiene, and a composition containing the same |
US20140274470A1 (en) * | 2013-03-14 | 2014-09-18 | Taylor Made Golf Company, Inc. | Golf ball compositions |
JP6232790B2 (ja) * | 2013-07-12 | 2017-11-22 | 横浜ゴム株式会社 | タイヤ用ゴム組成物および空気入りタイヤ |
KR101866674B1 (ko) * | 2014-05-08 | 2018-07-04 | 아르끄마 프랑스 | 경화성 우레탄 (메트)아크릴레이트 폴리머 조성물 및 방법 |
WO2016106062A1 (en) | 2014-12-23 | 2016-06-30 | Bridgestone Americas Tire Operations, Llc | Actinic radiation curable polymeric mixtures, cured polymeric mixtures and related processes |
JP6375224B2 (ja) * | 2014-12-26 | 2018-08-15 | 日立オートモティブシステムズ株式会社 | 熱硬化性樹脂組成物および該組成物を用いた回転電機 |
TWI555778B (zh) * | 2015-06-12 | 2016-11-01 | 國立清華大學 | 基底表面改質的方法 |
EP3351568A4 (en) * | 2015-09-16 | 2019-05-01 | Mitsui Chemicals Tohcello, Inc. | POLYFUNCTIONAL POLYMER AND METHOD FOR THE PRODUCTION THEREOF |
WO2017105960A1 (en) | 2015-12-17 | 2017-06-22 | Bridgestone Americas Tire Operations, Llc | Additive manufacturing cartridges and processes for producing cured polymeric products by additive manufacturing |
EP3184567A1 (de) | 2015-12-21 | 2017-06-28 | Evonik Degussa GmbH | Acrylatterminierte urethanpolybutadiene aus monomerarmen 1:1 monoaddukten aus reaktiven olfinischen verbindungen und diisocyanaten und hydroxyterminierten polybutadienen |
EP3184568A1 (en) | 2015-12-21 | 2017-06-28 | Evonik Degussa GmbH | Acrylate-terminated urethane polybutadienes from low-monomer 1:1 monoadductes from reactive olefinic compounds and diisocyanates and hydroxy-terminated polybutadienes for liquid optically clear adhesives (locas) |
KR102033338B1 (ko) * | 2016-08-11 | 2019-10-17 | 이노에프앤씨(주) | 디올 함유 지방족 우레탄 아크릴레이트 수지의 제조방법, 도광판용 광경화형 코팅 조성물, 투명 수지층 및 이를 이용한 터치 스크린 패널 |
WO2018081053A1 (en) | 2016-10-27 | 2018-05-03 | Bridgestone Americas Tire Operations, Llc | Processes for producing cured polymeric products by additive manufacturing |
CN107474752A (zh) * | 2017-08-29 | 2017-12-15 | 阜南县力韦包装材料有限公司 | 一种薄型双面胶的制备方法 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4179479A (en) * | 1978-04-20 | 1979-12-18 | Mobay Chemical Corporation | Thermoplastic polyurethane blends containing a processing aid |
JPS59227915A (ja) * | 1983-06-10 | 1984-12-21 | Nippon Telegr & Teleph Corp <Ntt> | 硬化性液状樹脂組成物およびこれを主成分とする光学繊維被覆材料 |
ATE38842T1 (de) * | 1984-07-20 | 1988-12-15 | Akzo Nv | Dispersion von additionspolymeren in organischen fluessigkeiten. |
EP1288247B1 (en) * | 2000-05-24 | 2008-07-16 | Kaneka Corporation | Curable compositions and compatibilizing agent |
JP2001329025A (ja) * | 2000-05-24 | 2001-11-27 | Kanegafuchi Chem Ind Co Ltd | ポリエーテル系重合体とビニル系重合体の相溶性を向上させる相溶化剤 |
JP4799755B2 (ja) | 2001-04-13 | 2011-10-26 | 日本曹達株式会社 | 液状ポリブタジエン(メタ)アクリレートの製造方法 |
US6552607B1 (en) | 2001-11-12 | 2003-04-22 | Apogee Technology Inc. | Time division multiplexed PWM amplifier |
DE60333927D1 (de) * | 2002-07-19 | 2010-10-07 | Zeon Corp | Verfahren zur herstellung eines hydrierten polymers |
WO2005019128A2 (en) * | 2003-08-20 | 2005-03-03 | Dsm Ip Assets B.V. | Radiation-curable liquid resin composition |
DE102005053678A1 (de) * | 2005-11-10 | 2007-05-16 | Bayer Materialscience Ag | Hydrophile Polyisocyanatgemische |
WO2008076286A1 (en) * | 2006-12-14 | 2008-06-26 | Dsm Ip Assets B.V. | D1370 r radiation curable secondary coating for optical fiber |
JP5132160B2 (ja) | 2007-02-02 | 2013-01-30 | 富士フイルム株式会社 | 硬化性組成物、カラーフィルタ、カラーフィルタの製造方法、及びグラフトポリマー |
JPWO2009057497A1 (ja) * | 2007-11-01 | 2011-03-10 | 株式会社クラレ | ポリウレタン組成物 |
CA2735442C (en) * | 2008-08-28 | 2018-09-11 | Interface Biologics Inc. | Thermally stable biuret and isocyanurate based surface modifying macromolecules and uses thereof |
JP2010174109A (ja) * | 2009-01-28 | 2010-08-12 | Bridgestone Corp | タイヤ |
JP2011116965A (ja) | 2009-11-09 | 2011-06-16 | Nippon Soda Co Ltd | 末端変性(水素添加)ポリブタジエン |
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US10414834B2 (en) | 2014-12-25 | 2019-09-17 | Kuraray Co., Ltd. | Modified liquid diene rubber and resin composition containing modified liquid diene rubber |
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WO2012039124A1 (ja) | 2012-03-29 |
JPWO2012039124A1 (ja) | 2014-02-03 |
EP2620455A4 (en) | 2014-07-09 |
KR20130059411A (ko) | 2013-06-05 |
CN103108891A (zh) | 2013-05-15 |
CN103108891B (zh) | 2014-08-27 |
KR101396747B1 (ko) | 2014-05-16 |
EP2620455B1 (en) | 2015-05-13 |
EP2620455A1 (en) | 2013-07-31 |
US20130165586A1 (en) | 2013-06-27 |
US8822600B2 (en) | 2014-09-02 |
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