CN104204000B - 用于制备高顺式聚二烯的方法 - Google Patents
用于制备高顺式聚二烯的方法 Download PDFInfo
- Publication number
- CN104204000B CN104204000B CN201380016276.2A CN201380016276A CN104204000B CN 104204000 B CN104204000 B CN 104204000B CN 201380016276 A CN201380016276 A CN 201380016276A CN 104204000 B CN104204000 B CN 104204000B
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- China
- Prior art keywords
- mercaptan
- compound
- lanthanide
- polydiene
- polymerization
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 48
- -1 mercaptan compound Chemical class 0.000 claims abstract description 158
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 126
- 150000002602 lanthanoids Chemical class 0.000 claims abstract description 90
- 229910052747 lanthanoid Inorganic materials 0.000 claims abstract description 84
- 239000000203 mixture Substances 0.000 claims abstract description 57
- 239000003054 catalyst Substances 0.000 claims abstract description 53
- 150000002601 lanthanoid compounds Chemical class 0.000 claims abstract description 48
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 45
- 150000002367 halogens Chemical class 0.000 claims abstract description 45
- 239000000178 monomer Substances 0.000 claims abstract description 42
- 239000002168 alkylating agent Substances 0.000 claims abstract description 41
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 41
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 40
- 239000003960 organic solvent Substances 0.000 claims abstract description 39
- 150000001993 dienes Chemical class 0.000 claims abstract description 29
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims abstract description 13
- 230000008569 process Effects 0.000 claims abstract description 13
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 89
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 33
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 26
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
- 239000011593 sulfur Substances 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 claims description 14
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 claims description 13
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 claims description 10
- LQERIDTXQFOHKA-UHFFFAOYSA-N nonadecane Chemical compound CCCCCCCCCCCCCCCCCCC LQERIDTXQFOHKA-UHFFFAOYSA-N 0.000 claims description 10
- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 claims description 10
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 claims description 10
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical class CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 claims description 8
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 claims description 8
- ZVEZMVFBMOOHAT-UHFFFAOYSA-N nonane-1-thiol Chemical compound CCCCCCCCCS ZVEZMVFBMOOHAT-UHFFFAOYSA-N 0.000 claims description 8
- 150000001336 alkenes Chemical class 0.000 claims description 7
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 claims description 7
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 claims description 7
- VPIAKHNXCOTPAY-UHFFFAOYSA-N Heptane-1-thiol Chemical compound CCCCCCCS VPIAKHNXCOTPAY-UHFFFAOYSA-N 0.000 claims description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 6
- ZRKMQKLGEQPLNS-UHFFFAOYSA-N 1-Pentanethiol Chemical compound CCCCCS ZRKMQKLGEQPLNS-UHFFFAOYSA-N 0.000 claims description 5
- ORTRWBYBJVGVQC-UHFFFAOYSA-N hexadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCS ORTRWBYBJVGVQC-UHFFFAOYSA-N 0.000 claims description 5
- NLAGNNORBYGNAV-UHFFFAOYSA-N isotriacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCC(C)C NLAGNNORBYGNAV-UHFFFAOYSA-N 0.000 claims description 5
- IPBROXKVGHZHJV-UHFFFAOYSA-N tridecane-1-thiol Chemical compound CCCCCCCCCCCCCS IPBROXKVGHZHJV-UHFFFAOYSA-N 0.000 claims description 4
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 claims description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 3
- IGLWCQMNTGCUBB-UHFFFAOYSA-N 3-methylidenepent-1-ene Chemical compound CCC(=C)C=C IGLWCQMNTGCUBB-UHFFFAOYSA-N 0.000 claims description 3
- AHIBWURJLGCHAY-UHFFFAOYSA-N [S].C1=CC=CC=C1 Chemical compound [S].C1=CC=CC=C1 AHIBWURJLGCHAY-UHFFFAOYSA-N 0.000 claims description 3
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 3
- 230000021615 conjugation Effects 0.000 claims 1
- 230000006872 improvement Effects 0.000 abstract description 15
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 description 67
- 229910052779 Neodymium Inorganic materials 0.000 description 63
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 60
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 59
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 40
- 239000002585 base Substances 0.000 description 28
- 229910052799 carbon Inorganic materials 0.000 description 25
- 239000004411 aluminium Substances 0.000 description 23
- 238000005984 hydrogenation reaction Methods 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 239000002253 acid Substances 0.000 description 20
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminum chloride Substances Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- 150000001721 carbon Chemical group 0.000 description 16
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 16
- 150000002430 hydrocarbons Chemical class 0.000 description 15
- 229910052749 magnesium Inorganic materials 0.000 description 14
- 239000004215 Carbon black (E152) Substances 0.000 description 13
- 229930195733 hydrocarbon Natural products 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 13
- 239000005062 Polybutadiene Substances 0.000 description 12
- 150000004703 alkoxides Chemical class 0.000 description 12
- 239000011777 magnesium Substances 0.000 description 12
- 229940091250 magnesium supplement Drugs 0.000 description 12
- 229920002857 polybutadiene Polymers 0.000 description 12
- 229920001971 elastomer Polymers 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000005060 rubber Substances 0.000 description 11
- OQOGEOLRYAOSKO-UHFFFAOYSA-N 1,1-dichloro-1-nitroethane Chemical compound CC(Cl)(Cl)[N+]([O-])=O OQOGEOLRYAOSKO-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 230000008859 change Effects 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 7
- 150000007942 carboxylates Chemical class 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 150000001924 cycloalkanes Chemical class 0.000 description 6
- 230000026030 halogenation Effects 0.000 description 6
- 238000005658 halogenation reaction Methods 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 125000004437 phosphorous atom Chemical group 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- 125000005234 alkyl aluminium group Chemical group 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 125000000962 organic group Chemical group 0.000 description 5
- 150000002901 organomagnesium compounds Chemical class 0.000 description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 5
- 125000003107 substituted aryl group Chemical group 0.000 description 5
- 125000002769 thiazolinyl group Chemical group 0.000 description 5
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 4
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 4
- WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- 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 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- VTXVGVNLYGSIAR-UHFFFAOYSA-N decane-1-thiol Chemical compound CCCCCCCCCCS VTXVGVNLYGSIAR-UHFFFAOYSA-N 0.000 description 4
- SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- 239000012990 dithiocarbamate Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 229910001502 inorganic halide Inorganic materials 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- 229910052746 lanthanum Inorganic materials 0.000 description 4
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 4
- 229910001507 metal halide Inorganic materials 0.000 description 4
- 150000005309 metal halides Chemical class 0.000 description 4
- 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 4
- 125000001117 oleyl 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])=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 4
- 150000002896 organic halogen compounds Chemical class 0.000 description 4
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 4
- 150000003009 phosphonic acids Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 4
- GNLJBJNONOOOQC-UHFFFAOYSA-N $l^{3}-carbane;magnesium Chemical compound [Mg]C GNLJBJNONOOOQC-UHFFFAOYSA-N 0.000 description 3
- LXUNZSDDXMPKLP-UHFFFAOYSA-N 2-Methylbenzenethiol Chemical compound CC1=CC=CC=C1S LXUNZSDDXMPKLP-UHFFFAOYSA-N 0.000 description 3
- MPBLPZLNKKGCGP-UHFFFAOYSA-N 2-methyloctane-2-thiol Chemical compound CCCCCCC(C)(C)S MPBLPZLNKKGCGP-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 229910000722 Didymium Inorganic materials 0.000 description 3
- 241000224487 Didymium Species 0.000 description 3
- 229910052688 Gadolinium Inorganic materials 0.000 description 3
- 241001441571 Hiodontidae Species 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 229910052772 Samarium Inorganic materials 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 229910021623 Tin(IV) bromide Inorganic materials 0.000 description 3
- ADSXDBCZNVXTRD-UHFFFAOYSA-N [Mg]C1=CC=CC=C1 Chemical compound [Mg]C1=CC=CC=C1 ADSXDBCZNVXTRD-UHFFFAOYSA-N 0.000 description 3
- GUDBSTJKAWCJQP-UHFFFAOYSA-N [Mg]CC1=CC=CC=C1 Chemical compound [Mg]CC1=CC=CC=C1 GUDBSTJKAWCJQP-UHFFFAOYSA-N 0.000 description 3
- AQLUYLRUKQKIIR-UHFFFAOYSA-N [Nd].C(C)C(CP(O)=O)CCCC Chemical compound [Nd].C(C)C(CP(O)=O)CCCC AQLUYLRUKQKIIR-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 150000001399 aluminium compounds Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 3
- 229910021386 carbon form Inorganic materials 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- ZJAZLUUIDQUJQE-UHFFFAOYSA-N formic acid;neodymium Chemical compound [Nd].OC=O ZJAZLUUIDQUJQE-UHFFFAOYSA-N 0.000 description 3
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 150000002681 magnesium compounds Chemical class 0.000 description 3
- KJJBSBKRXUVBMX-UHFFFAOYSA-N magnesium;butane Chemical compound [Mg+2].CCC[CH2-].CCC[CH2-] KJJBSBKRXUVBMX-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000002577 pseudohalo group Chemical group 0.000 description 3
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 3
- 230000003019 stabilising effect Effects 0.000 description 3
- 239000012991 xanthate 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
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 2
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
- QZLAEIZEPJAELS-UHFFFAOYSA-N 2,4,4-trimethylpentane-2-thiol Chemical compound CC(C)(C)CC(C)(C)S QZLAEIZEPJAELS-UHFFFAOYSA-N 0.000 description 2
- GMKMEZVLHJARHF-UHFFFAOYSA-N 2,6-diaminopimelic acid Chemical compound OC(=O)C(N)CCCC(N)C(O)=O GMKMEZVLHJARHF-UHFFFAOYSA-N 0.000 description 2
- IQIBYAHJXQVQGB-UHFFFAOYSA-N 2-methylbutane-2-thiol Chemical compound CCC(C)(C)S IQIBYAHJXQVQGB-UHFFFAOYSA-N 0.000 description 2
- RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- UBDHSURDYAETAL-UHFFFAOYSA-N 8-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 UBDHSURDYAETAL-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- LXAANKZZFVRCLZ-UHFFFAOYSA-N CC(CCCCCC)P(O)=O.[Nd] Chemical compound CC(CCCCCC)P(O)=O.[Nd] LXAANKZZFVRCLZ-UHFFFAOYSA-N 0.000 description 2
- KKUZFMJIXIFTND-UHFFFAOYSA-N CCCCCC[Mg] Chemical compound CCCCCC[Mg] KKUZFMJIXIFTND-UHFFFAOYSA-N 0.000 description 2
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- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- NLLZTRMHNHVXJJ-UHFFFAOYSA-J titanium tetraiodide Chemical compound I[Ti](I)(I)I NLLZTRMHNHVXJJ-UHFFFAOYSA-J 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- MCWWHQMTJNSXPX-UHFFFAOYSA-N tribenzylalumane Chemical compound C=1C=CC=CC=1C[Al](CC=1C=CC=CC=1)CC1=CC=CC=C1 MCWWHQMTJNSXPX-UHFFFAOYSA-N 0.000 description 1
- JKNHZOAONLKYQL-UHFFFAOYSA-K tribromoindigane Chemical compound Br[In](Br)Br JKNHZOAONLKYQL-UHFFFAOYSA-K 0.000 description 1
- FVRKTAOFDKFAMI-UHFFFAOYSA-M tributylstannanylium;bromide Chemical compound [Br-].CCCC[Sn+](CCCC)CCCC FVRKTAOFDKFAMI-UHFFFAOYSA-M 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- IIYFAKIEWZDVMP-NJFSPNSNSA-N tridecane Chemical compound CCCCCCCCCCCC[14CH3] IIYFAKIEWZDVMP-NJFSPNSNSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- XRADHEAKQRNYQQ-UHFFFAOYSA-K trifluoroneodymium Chemical compound F[Nd](F)F XRADHEAKQRNYQQ-UHFFFAOYSA-K 0.000 description 1
- RMUKCGUDVKEQPL-UHFFFAOYSA-K triiodoindigane Chemical compound I[In](I)I RMUKCGUDVKEQPL-UHFFFAOYSA-K 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- LYRCQNDYYRPFMF-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C LYRCQNDYYRPFMF-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
- JQPMDTQDAXRDGS-UHFFFAOYSA-N triphenylalumane Chemical compound C1=CC=CC=C1[Al](C=1C=CC=CC=1)C1=CC=CC=C1 JQPMDTQDAXRDGS-UHFFFAOYSA-N 0.000 description 1
- CCIDWXHLGNEQSL-UHFFFAOYSA-N undecane-1-thiol Chemical compound CCCCCCCCCCCS CCIDWXHLGNEQSL-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F136/04—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F136/06—Butadiene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F36/06—Butadiene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/54—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with other compounds thereof
- C08F4/545—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with other compounds thereof rare earths being present, e.g. triethylaluminium + neodymium octanoate
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261603658P | 2012-02-27 | 2012-02-27 | |
| US61/603,658 | 2012-02-27 | ||
| PCT/US2013/027905 WO2013130522A1 (en) | 2012-02-27 | 2013-02-27 | Processes for the preparation of high-cis polydienes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104204000A CN104204000A (zh) | 2014-12-10 |
| CN104204000B true CN104204000B (zh) | 2016-08-24 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380016276.2A Active CN104204000B (zh) | 2012-02-27 | 2013-02-27 | 用于制备高顺式聚二烯的方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US9353205B2 ( ) |
| EP (1) | EP2820054B1 ( ) |
| JP (1) | JP6231997B2 ( ) |
| KR (1) | KR101975074B1 ( ) |
| CN (1) | CN104204000B ( ) |
| BR (1) | BR112014021261B1 ( ) |
| SG (1) | SG11201404817VA ( ) |
| WO (1) | WO2013130522A1 ( ) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160060562A (ko) | 2014-11-20 | 2016-05-30 | 주식회사 엘지화학 | 공액 디엔계 중합체 |
| WO2016080766A1 (ko) * | 2014-11-20 | 2016-05-26 | 주식회사 엘지화학 | 공액 디엔계 중합체의 제조방법 |
| WO2016080765A1 (ko) * | 2014-11-20 | 2016-05-26 | 주식회사 엘지화학 | 공액 디엔계 중합체 |
| KR101781699B1 (ko) * | 2014-11-20 | 2017-09-25 | 주식회사 엘지화학 | 공액 디엔의 중합용 촉매 조성물 |
| KR101796360B1 (ko) | 2014-11-20 | 2017-11-09 | 주식회사 엘지화학 | 공액 디엔계 중합체의 제조방법 |
| WO2017100315A1 (en) * | 2015-12-07 | 2017-06-15 | Bridgestone Corporation | Polybutadiene polymers and rubber compositions incorporating same for low temperature applications |
| KR102122469B1 (ko) * | 2016-11-01 | 2020-06-12 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이의 제조방법 |
| KR102295653B1 (ko) | 2017-11-22 | 2021-08-31 | 주식회사 엘지화학 | 공액디엔계 중합체 및 이의 제조방법 |
| US12264232B2 (en) * | 2019-05-14 | 2025-04-01 | Bridgestone Corporation | Modified high-cis polybutadiene polymer, related methods and tire components |
| US20220289871A1 (en) * | 2019-09-19 | 2022-09-15 | Lg Chem, Ltd. | Method for Preparing Modified Conjugated Diene-Based Polymer |
| EP3838932B1 (en) | 2019-12-20 | 2022-08-10 | The Goodyear Tire & Rubber Company | Synthesis of isoprene-butadiene copolymer rubbers |
| US11584808B2 (en) | 2019-12-30 | 2023-02-21 | Bridgestone Corporation | Polymerization catalyst composition and method of employing same |
| CN114957526B (zh) * | 2021-02-24 | 2024-03-26 | 中国石油化工股份有限公司 | 一种立构嵌段聚共轭二烯烃及其制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101456928A (zh) * | 2007-12-12 | 2009-06-17 | 锦湖石油化学株式会社 | 芳族有机硫官能化的1,4-顺式聚丁二烯 |
Family Cites Families (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3297667A (en) | 1963-02-28 | 1967-01-10 | Union Carbide Corp | Production of cis-1, 4-polydienes by polymerization of 1, 3-dienes |
| DE2830080A1 (de) | 1978-07-08 | 1980-01-17 | Bayer Ag | Katalysator, dessen herstellung und verwendung zur loesungspolymerisation von butadien |
| CA1223396A (en) | 1981-06-29 | 1987-06-23 | Tooru Shibata | Process for producing conjugated diene polymer |
| CA1212932A (en) | 1982-04-01 | 1986-10-21 | Derek K. Jenkins | Polymerisation of conjugated dienes |
| JPS5945337A (ja) | 1982-09-07 | 1984-03-14 | Japan Synthetic Rubber Co Ltd | 生強度の改良されたポリブタジエンゴム組成物 |
| US4699962A (en) | 1984-01-30 | 1987-10-13 | Phillips Petroleum Company | Olefin polymerization |
| US4575538A (en) | 1984-12-20 | 1986-03-11 | Phillips Petroleum Company | Olefin polymerization |
| IT1191614B (it) | 1985-05-15 | 1988-03-23 | Enichem Elastomers | Procedimento migliorato per la polimerizzazione o copolimerizzazione del butadiene |
| IT1191612B (it) | 1985-05-15 | 1988-03-23 | Enichem Elastomers | Procedimento migliorato per la polimerizzazione o copolimerizzazione del butadiene |
| IT1186730B (it) | 1985-06-05 | 1987-12-16 | Enichem Elastomers | Procedimento per la polimerizzazione di isoprene |
| US4663405A (en) | 1986-04-16 | 1987-05-05 | The Goodyear Tire & Rubber Company | Molecular weight modifier for use with lanthanide and actinide catalysts |
| US5064910A (en) | 1986-09-05 | 1991-11-12 | Japan Synthetic Rubber Co., Ltd. | Preparation of conjugated diene polymers modified with an organo-tin or germanium halide |
| US4906706A (en) | 1986-09-05 | 1990-03-06 | Japan Synthetic Rubber Co., Ltd. | Modified conjugated diene polymer and process for production thereof |
| GB8830007D0 (en) | 1988-12-22 | 1989-02-15 | Enichem Elastomers | Polymerization of butadiene |
| IT1230756B (it) | 1989-02-17 | 1991-10-29 | Enichem Elastomers | Metodo per la preparazione di polibutadiene a lavorabilita' migliorata. |
| US5405815A (en) * | 1993-06-17 | 1995-04-11 | The Goodyear Tire & Rubber Company | Process for preparing a catalyst system useful in the synthesis of isoprene-butadiene rubber |
| US6384156B1 (en) | 1994-08-02 | 2002-05-07 | Union Carbide Chemicals & Plastics Technology Corporation | Gas phase polymerization process |
| DE4436059A1 (de) | 1994-10-10 | 1996-04-11 | Bayer Ag | Verfahren zur Herstellung von mittels Nd-Katalysatoren polymerisierten Dienkautschuken mit niedrigem cold-flow und geringem Eigengeruch |
| JPH10330541A (ja) * | 1997-05-29 | 1998-12-15 | Yokohama Rubber Co Ltd:The | 変性ポリブタジエンゴム及びそれを含むゴム組成物 |
| US6255416B1 (en) | 1998-05-13 | 2001-07-03 | Jsr Corporation | Method of producing conjugated diene polymers |
| JP4038916B2 (ja) | 1999-02-03 | 2008-01-30 | Ｊｓｒ株式会社 | 共役ジエン系重合体の製造方法 |
| US6437205B1 (en) | 1999-05-19 | 2002-08-20 | Bridgestone Corporation | Low molecular weight high-cis polybutadienes and their use in high molecular weight-low molecular weight high-cis polybutadiene blends |
| KR100352764B1 (ko) | 2000-03-16 | 2002-09-16 | 금호석유화학 주식회사 | 신규한 단분자 니오디뮴 카르복실레이트 화합물 및 이를포함하는 디엔 중합용 촉매 |
| WO2002068484A1 (en) | 2001-02-28 | 2002-09-06 | Bridgestone Corporation | Continuous process for the production of conjugated diene polymers having narrow molecular weight distribution and products therefrom |
| TW575586B (en) | 2001-04-12 | 2004-02-11 | Ube Industries | Method of polymerizing ethylenically unsaturated monomer |
| ZA200210309B (en) * | 2001-12-31 | 2003-07-03 | Goodyear Tire & Rubber | Group III-B metal catalyst system. |
| KR100462662B1 (ko) | 2002-08-05 | 2004-12-20 | 금호석유화학 주식회사 | 초분지형 고 1,4-시스 폴리부타디엔의 제조방법 |
| US7008899B2 (en) | 2003-08-11 | 2006-03-07 | Bridgestone Corporation | Lanthanide-based catalyst composition for producing cis-1,4-polydienes |
| CN1528794A (zh) | 2003-09-25 | 2004-09-15 | 中国科学院长春应用化学研究所 | 稀土顺丁橡胶分子质量分布的调节方法 |
| US7094849B2 (en) | 2003-12-15 | 2006-08-22 | Bridgestone Corporation | Bulk polymerization process for producing polydienes |
| JP5111101B2 (ja) | 2004-03-02 | 2012-12-26 | 株式会社ブリヂストン | バルク重合プロセス |
| EP1816145B1 (en) | 2004-11-01 | 2014-01-15 | Ube Industries, Ltd. | Polymerization catalyst for conjugated diene polymer, process for producing conjugated diene polymer with the same, rubber composition for tire, and rubber composition for golf ball |
| JP2007023232A (ja) * | 2005-07-21 | 2007-02-01 | Ube Ind Ltd | 新規なビニル・シスポリブタジエンゴムの製造方法 |
| FR2899903B1 (fr) | 2006-04-14 | 2012-01-06 | Michelin Soc Tech | Procede de preparation d'un elastomere dienique, tel qu'un polybutadiene. |
| JP5508016B2 (ja) | 2006-10-06 | 2014-05-28 | 株式会社ブリヂストン | 分岐重合体、並びにその合成方法及び使用方法 |
| ZA200711158B (en) | 2006-12-28 | 2009-03-25 | Bridgestone Corp | A method for producing functionalized cis-1,4-polydienes having high cis-1,4-linkage content and high functionality |
| US7594528B2 (en) * | 2007-03-08 | 2009-09-29 | The Goodyear Tire & Rubber Company | Tire with sidewall comprised of emulsion styrene/butadiene rubber, cis 1,4-polyisoprene rubber and cis 1,4-polybutadiene rubber |
| US7572867B2 (en) | 2007-05-01 | 2009-08-11 | Bridgestone Corporation | Polymerization process for producing polydienes |
| US7741418B2 (en) | 2007-12-31 | 2010-06-22 | Bridgestone Corporation | Process for producing polydienes |
| US7825201B2 (en) | 2007-12-31 | 2010-11-02 | Bridgestone Corporation | Process for producing polydienes |
| US7807763B2 (en) | 2008-04-07 | 2010-10-05 | Bridgestone Corporation | Method for bulk polymerization |
-
2013
- 2013-02-27 US US14/380,944 patent/US9353205B2/en active Active
- 2013-02-27 SG SG11201404817VA patent/SG11201404817VA/en unknown
- 2013-02-27 KR KR1020147023458A patent/KR101975074B1/ko not_active Expired - Fee Related
- 2013-02-27 BR BR112014021261-9A patent/BR112014021261B1/pt not_active IP Right Cessation
- 2013-02-27 JP JP2014558956A patent/JP6231997B2/ja not_active Expired - Fee Related
- 2013-02-27 CN CN201380016276.2A patent/CN104204000B/zh active Active
- 2013-02-27 WO PCT/US2013/027905 patent/WO2013130522A1/en active Application Filing
- 2013-02-27 EP EP13755152.9A patent/EP2820054B1/en active Active
-
2016
- 2016-05-26 US US15/165,552 patent/US9868801B2/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101456928A (zh) * | 2007-12-12 | 2009-06-17 | 锦湖石油化学株式会社 | 芳族有机硫官能化的1,4-顺式聚丁二烯 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2013130522A1 (en) | 2013-09-06 |
| US9868801B2 (en) | 2018-01-16 |
| EP2820054B1 (en) | 2017-04-05 |
| EP2820054A4 (en) | 2015-07-15 |
| SG11201404817VA (en) | 2014-09-26 |
| US20160264698A1 (en) | 2016-09-15 |
| JP6231997B2 (ja) | 2017-11-15 |
| BR112014021261A2 (pt) | 2021-01-26 |
| KR101975074B1 (ko) | 2019-05-03 |
| US20150299350A1 (en) | 2015-10-22 |
| KR20140129048A (ko) | 2014-11-06 |
| BR112014021261B1 (pt) | 2021-08-31 |
| US9353205B2 (en) | 2016-05-31 |
| EP2820054A1 (en) | 2015-01-07 |
| CN104204000A (zh) | 2014-12-10 |
| JP2015508843A (ja) | 2015-03-23 |
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