DE3514063A1 - Katalysator und verfahren zur hydrierung von olefinische doppelbindungen enthaltenden dien-polymeren und dien-copolymeren - Google Patents
Katalysator und verfahren zur hydrierung von olefinische doppelbindungen enthaltenden dien-polymeren und dien-copolymerenInfo
- Publication number
- DE3514063A1 DE3514063A1 DE19853514063 DE3514063A DE3514063A1 DE 3514063 A1 DE3514063 A1 DE 3514063A1 DE 19853514063 DE19853514063 DE 19853514063 DE 3514063 A DE3514063 A DE 3514063A DE 3514063 A1 DE3514063 A1 DE 3514063A1
- Authority
- DE
- Germany
- Prior art keywords
- polymer
- hydrogenation
- copolymer
- blocks
- catalyst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims description 161
- 239000003054 catalyst Substances 0.000 title claims description 127
- 229920001577 copolymer Polymers 0.000 title claims description 94
- 238000000034 method Methods 0.000 title claims description 42
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 title 1
- 238000005984 hydrogenation reaction Methods 0.000 claims description 179
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 66
- 229920001400 block copolymer Polymers 0.000 claims description 60
- 150000001993 dienes Chemical class 0.000 claims description 59
- 229920002554 vinyl polymer Polymers 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000010936 titanium Substances 0.000 claims description 27
- 229910052744 lithium Inorganic materials 0.000 claims description 25
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 24
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 24
- 229910052719 titanium Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 17
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 13
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000002900 organolithium compounds Chemical class 0.000 claims description 4
- 150000002642 lithium compounds Chemical class 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 84
- 239000000243 solution Substances 0.000 description 42
- 238000004519 manufacturing process Methods 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 24
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 21
- 230000000694 effects Effects 0.000 description 20
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 19
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 11
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 10
- 229920001971 elastomer Polymers 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 230000014759 maintenance of location Effects 0.000 description 8
- 230000004048 modification Effects 0.000 description 8
- 238000012986 modification Methods 0.000 description 8
- 229920002725 thermoplastic elastomer Polymers 0.000 description 8
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 239000000806 elastomer Substances 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 239000005062 Polybutadiene Substances 0.000 description 5
- UREWAKSZTRITCZ-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 UREWAKSZTRITCZ-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 230000009849 deactivation Effects 0.000 description 5
- -1 diaryl titanocene compound Chemical class 0.000 description 5
- 239000001307 helium Substances 0.000 description 5
- 229910052734 helium Inorganic materials 0.000 description 5
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 5
- 230000036571 hydration Effects 0.000 description 5
- 238000006703 hydration reaction Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229920002857 polybutadiene Polymers 0.000 description 5
- 230000001603 reducing effect Effects 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000002638 heterogeneous catalyst Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 239000002952 polymeric resin Substances 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical class [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 description 3
- 239000002815 homogeneous catalyst Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-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
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- URFPRAHGGBYNPW-UHFFFAOYSA-N 1-bromo-4-ethylbenzene Chemical compound CCC1=CC=C(Br)C=C1 URFPRAHGGBYNPW-UHFFFAOYSA-N 0.000 description 2
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 241000158147 Sator Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000010734 process oil Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 229940116351 sebacate Drugs 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 1
- ZMYIIHDQURVDRB-UHFFFAOYSA-N 1-phenylethenylbenzene Chemical group C=1C=CC=CC=1C(=C)C1=CC=CC=C1 ZMYIIHDQURVDRB-UHFFFAOYSA-N 0.000 description 1
- BIOCRZSYHQYVSG-UHFFFAOYSA-N 2-(4-ethenylphenyl)-n,n-diethylethanamine Chemical compound CCN(CC)CCC1=CC=C(C=C)C=C1 BIOCRZSYHQYVSG-UHFFFAOYSA-N 0.000 description 1
- OHDSHGBRKMRPHC-UHFFFAOYSA-N 2-(4-ethenylphenyl)-n,n-dimethylethanamine Chemical compound CN(C)CCC1=CC=C(C=C)C=C1 OHDSHGBRKMRPHC-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- OCTVDLUSQOJZEK-UHFFFAOYSA-N 4,5-diethylocta-1,3-diene Chemical compound CCCC(CC)C(CC)=CC=C OCTVDLUSQOJZEK-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- UGWOAPBVIGCNOV-UHFFFAOYSA-N 5-ethenyldec-5-ene Chemical compound CCCCC=C(C=C)CCCC UGWOAPBVIGCNOV-UHFFFAOYSA-N 0.000 description 1
- OWJHNUOZBNPLDR-UHFFFAOYSA-N C1=CC=CC1[Ti](CC)(CC)C1C=CC=C1 Chemical compound C1=CC=CC1[Ti](CC)(CC)C1C=CC=C1 OWJHNUOZBNPLDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241001481828 Glyptocephalus cynoglossus Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical class CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- QARVLSVVCXYDNA-IDEBNGHGSA-N bromobenzene Chemical group Br[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 QARVLSVVCXYDNA-IDEBNGHGSA-N 0.000 description 1
- JRKOSYZXHJZKLA-UHFFFAOYSA-N buta-1,3-diene styrene Chemical compound C=CC=C.C=Cc1ccccc1.C=Cc1ccccc1.C=Cc1ccccc1 JRKOSYZXHJZKLA-UHFFFAOYSA-N 0.000 description 1
- ONRUPSRTXJQYOT-UHFFFAOYSA-N buta-1,3-diene styrene Chemical compound C=CC=C.C=CC=C.C=CC=C.C=Cc1ccccc1.C=Cc1ccccc1 ONRUPSRTXJQYOT-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- YNBJMIXWGPOBGE-UHFFFAOYSA-N carbanide;cyclopenta-1,3-diene;titanium(4+) Chemical compound [CH3-].[CH3-].[Ti+4].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 YNBJMIXWGPOBGE-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000012718 coordination polymerization Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- XKLWATAZDMHTSH-UHFFFAOYSA-L cyclopentane;dichlorotitanium Chemical compound Cl[Ti]Cl.[CH]1[CH][CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1 XKLWATAZDMHTSH-UHFFFAOYSA-L 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002641 lithium Chemical group 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920003047 styrene-styrene-butadiene-styrene Polymers 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/02—Hydrogenation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/04—Reduction, e.g. hydrogenation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
- B01J2531/46—Titanium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59076614A JPS60220147A (ja) | 1984-04-18 | 1984-04-18 | オレフイン水添触媒および該触媒を用いた重合体の水添方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3514063A1 true DE3514063A1 (de) | 1985-11-07 |
| DE3514063C2 DE3514063C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-12-06 |
Family
ID=13610221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853514063 Granted DE3514063A1 (de) | 1984-04-18 | 1985-04-18 | Katalysator und verfahren zur hydrierung von olefinische doppelbindungen enthaltenden dien-polymeren und dien-copolymeren |
Country Status (5)
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0397026A1 (en) * | 1989-05-09 | 1990-11-14 | The Dow Chemical Company | Process for hydrogenation of polymers |
| FR2650964A1 (fr) * | 1988-04-28 | 1991-02-22 | Japan Synthetic Rubber Co Ltd | Catalyseur d'hydrogenation a base de compose du titane et procede d'hydrogenation l'utilisant |
| EP0460725A1 (en) * | 1990-05-29 | 1991-12-11 | Shell Internationale Researchmaatschappij B.V. | Selective hydrogenation of conjugated diolefin polymers |
| EP0471415A1 (en) * | 1990-08-15 | 1992-02-19 | Shell Internationale Researchmaatschappij B.V. | Selective hydrogenation of conjugated diolefin polymers |
| EP0544304A1 (en) * | 1991-11-28 | 1993-06-02 | Japan Synthetic Rubber Co., Ltd. | Catalyst composition for hydrogenating olefinically unsaturated polymers |
| EP0545844A1 (en) * | 1991-12-05 | 1993-06-09 | Repsol Quimica S.A. | Process for the hydrogenation of compounds with an olefinic unsaturation |
| WO2018060016A1 (en) * | 2016-09-27 | 2018-04-05 | Basf Se | Star-shaped and triblock polymers with enhanced crosslinkability |
Families Citing this family (102)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4851488A (en) * | 1987-04-23 | 1989-07-25 | Shell Oil Company | Process for altering hydrogenated polymer compositions from high melt flow to low melt flow |
| US5017660A (en) * | 1987-08-04 | 1991-05-21 | Asahi Kasei Kogyo Kabushiki Kaisha | Selectively, partially hydrogenated polymer and rubber composition and impact resistant styrenic resin containing the same |
| US4914160A (en) * | 1988-06-23 | 1990-04-03 | Hormoz Azizian | Deuteration of unsaturated polymers and copolymers |
| US5549964A (en) * | 1988-12-27 | 1996-08-27 | Asahi Kasei Kogyo Kabushiki Kaisha | Stretchable nonwoven fabric and method of manufacturing the same |
| JP2969771B2 (ja) * | 1989-12-22 | 1999-11-02 | ジェイエスアール株式会社 | オレフィン性不飽和重合体の水素添加方法および水素添加用触媒組成物 |
| US5149895A (en) * | 1990-01-16 | 1992-09-22 | Mobil Oil Corporation | Vulcanizable liquid compositions |
| US5187236A (en) * | 1990-01-16 | 1993-02-16 | Mobil Oil Corporation | Solid block and random elastomeric copolymers |
| US5436305A (en) * | 1991-05-09 | 1995-07-25 | Phillips Petroleum Company | Organometallic fluorenyl compounds, preparation, and use |
| US5177155A (en) * | 1991-05-13 | 1993-01-05 | Shell Oil Company | Selective hydrogenation of conjugation diolefin polymers with rare earth catalysts |
| US5132372A (en) * | 1991-09-09 | 1992-07-21 | Shell Oil Company | Process for selective hydrogenation of conjugated diolefin polymers |
| US5206307A (en) * | 1991-09-09 | 1993-04-27 | Shell Oil Company | Process for selective hydrogenation of conjugated diolefin polymers |
| US5173537A (en) * | 1991-12-20 | 1992-12-22 | Shell Oil Company | Selective hydrogenation of conjugated diolefin poylmers |
| US5242961A (en) * | 1992-05-28 | 1993-09-07 | Shell Oil Company | Color prevention in titanium catalyzed hydrogenated diene polymers |
| US5242986A (en) * | 1992-08-10 | 1993-09-07 | Shell Oil Company | Selective partial hydrogenation of conjugated diolefin polymers |
| US5399632A (en) * | 1992-09-30 | 1995-03-21 | Exxon Research & Engineering Co. | Hydrogenation process for unsaturated homo and copolymers |
| ES2050620B1 (es) * | 1992-11-03 | 1994-12-16 | Repsol Quimica Sa | Procedimiento de hidrogenacion en disolucion de los dobles enlaces de polimeros de dienos conjugados y copolimero bloque hidrogenado producido. |
| US5244980A (en) * | 1992-12-07 | 1993-09-14 | Shell Oil Company | Selective hydrogenation of conjugated diolefin polymers with Tebbe's reagent |
| FI97141C (fi) * | 1994-03-14 | 1996-10-25 | Neste Oy | Menetelmä tyydyttämättömien polymeerien selektiiviseksi hydrogenoimiseksi |
| AU4419496A (en) * | 1994-12-12 | 1996-07-03 | Dow Chemical Company, The | Hydrogenation of unsaturated polymers using monocyclopentadienyl group iv metal catalysts |
| KR100201228B1 (ko) * | 1995-10-17 | 1999-06-15 | 박찬구 | 리빙중합체의 수첨방법 |
| CN1130383C (zh) * | 1996-03-15 | 2003-12-10 | 国际壳牌研究有限公司 | 共轭二烯聚合物的氢化方法及其适用的催化剂组合物 |
| US5814709A (en) * | 1996-04-12 | 1998-09-29 | Shell Oil Company | Process for hydrogenation on conjugataed diene polymers and catalyst composition suitable for use therein |
| KR0182835B1 (ko) * | 1996-04-26 | 1999-05-15 | 김흥기 | 올레핀성 이중결합을 갖는 리빙중합체의 선택적 수소화 방법 |
| US5705571A (en) * | 1996-05-17 | 1998-01-06 | Taiwan Synthetic Rubber Corporation | Process for selective hydrogenation of conjugated diene polymer |
| JPH1053614A (ja) * | 1996-05-29 | 1998-02-24 | Shell Internatl Res Maatschappij Bv | 共役ジエンポリマーの水素化のためのプロセスとこのプロセスで使用するのに適した触媒組成物 |
| JPH10101727A (ja) * | 1996-09-24 | 1998-04-21 | Shell Internatl Res Maatschappij Bv | オレフィン又はポリマーを水素化するための触媒及び方法 |
| DE19815895C2 (de) * | 1997-04-09 | 2000-04-13 | Asahi Chemical Ind | Hydrierte Blockcopolymere, diese enthaltende Zusammensetzungen und Formkörper |
| US5985995A (en) * | 1997-06-20 | 1999-11-16 | Repsol Quimica, S.A. | Process for producing hydrogenated rubbers |
| KR100219260B1 (ko) * | 1997-07-24 | 1999-09-01 | 박찬구 | 리빙 중합체 수첨용 신규 촉매 및 촉매를 이용한 수첨방법 |
| US6187873B1 (en) * | 1997-08-07 | 2001-02-13 | Shell Oil Company | Increased throughput in the manufacture of block copolymers by reduction in polymer cement viscosity through the addition of polar solvents |
| KR100264514B1 (ko) * | 1998-03-12 | 2000-09-01 | 박찬구 | 공역디엔 중합체의 수소화 방법 |
| KR100348761B1 (ko) | 1999-11-26 | 2002-08-13 | 금호석유화학 주식회사 | 공액디엔을 포함하는 중합체의 선택적 수소화 방법 |
| DE60111394T2 (de) * | 2000-07-28 | 2005-11-24 | Kraton Polymers Research B.V. | Verfahren zur herstellung von teilhydrierten butadienpolymeren |
| JP4761697B2 (ja) * | 2000-10-25 | 2011-08-31 | 旭化成ケミカルズ株式会社 | 水添重合体 |
| KR100411861B1 (ko) | 2000-11-28 | 2003-12-18 | 금호석유화학 주식회사 | 유기티타늄 화합물로 선택적으로 수소화된 중합체로부터금속 촉매를 제거하는 방법 |
| CN100347205C (zh) | 2001-04-11 | 2007-11-07 | 旭化成株式会社 | 氢化聚合物及其生产方法 |
| DE10129608A1 (de) * | 2001-06-20 | 2003-05-28 | Tesa Ag | Stripfähige Systeme auf Basis von Acrylatblockcopolymeren |
| ATE509038T1 (de) * | 2001-07-18 | 2011-05-15 | Asahi Kasei Chemicals Corp | Modifiziertes blockcopolymer |
| DE60225175T2 (de) * | 2001-10-23 | 2009-02-12 | Asahi Kasei Kabushiki Kaisha | Hydriertes copolymer |
| WO2003091339A1 (fr) * | 2002-04-24 | 2003-11-06 | Asahi Kasei Chemicals Corporation | Composition d'asphalte |
| KR100515452B1 (ko) * | 2003-01-04 | 2005-09-20 | 금호석유화학 주식회사 | 고속분사 노즐 장착 반응기로부터 제조된 리튬하이드라이드를 사용하여 선택적으로 수소화된 공역디엔 중합체를 제조하는 방법 |
| TWI259198B (en) * | 2003-10-10 | 2006-08-01 | Asahi Kasei Chemicals Corp | Polyoxymethylene resin composition and its moldings |
| US7794807B2 (en) | 2004-09-07 | 2010-09-14 | Denki Kagaku Kogyo Kabushiki Kaisha | Conductive composite sheeting |
| EP1908795B1 (en) | 2005-05-19 | 2011-08-10 | Mitsui Chemicals, Inc. | Resin composition for foam and use thereof |
| CN101268107B (zh) | 2005-09-22 | 2012-10-10 | 旭化成化学株式会社 | 共轭二烯系聚合物及其制造方法 |
| US20090312449A1 (en) * | 2006-02-13 | 2009-12-17 | Shigeru Sasaki | Hydrogenated block copolymer, resin composition comprising the hydrogenated block copolymer, and crosslinked product and crosslinked foamed product thereof |
| CN101495522B (zh) | 2006-07-24 | 2012-03-14 | 旭化成化学株式会社 | 改性共轭二烯系聚合物及其制造方法 |
| WO2008062779A1 (fr) | 2006-11-22 | 2008-05-29 | Techno Polymer Co., Ltd. | Composition de résine pour revêtement métallique, article moulé de cette composition et article moulé à revêtement métallique |
| WO2008084512A1 (ja) | 2006-12-26 | 2008-07-17 | Asahi Kasei E-Materials Corporation | 放熱材料及び放熱材料で成形した放熱シート |
| US8541504B2 (en) | 2007-02-20 | 2013-09-24 | Asahi Kasei Chemicals Corporation | Impact absorber composition |
| JP5357012B2 (ja) * | 2007-03-26 | 2013-12-04 | 旭化成ケミカルズ株式会社 | 熱可塑性組成物及びその成形体 |
| US8278395B2 (en) | 2007-03-28 | 2012-10-02 | Asahi Kasei Chemicals Corporation | Process for manufacturing modified conjugated diene polymer, composition comprising the polymer, and tire comprising the composition |
| ITMI20070626A1 (it) * | 2007-03-29 | 2008-09-30 | Polimeri Europa Spa | Mescola vulcanizzabile comprendente copolineri ramificati vinilarene-diene coniugato parzialmente idrogenati |
| KR100910255B1 (ko) | 2007-10-08 | 2009-07-31 | 금호석유화학 주식회사 | 수소화된 공역디엔계 중합체의 제조방법 |
| US20090131597A1 (en) * | 2007-11-21 | 2009-05-21 | Young Hoon Ko | Process for the preparation of a hydrogenated conjugated diene-based polymer |
| EP2258771B1 (en) | 2008-03-25 | 2012-10-31 | Asahi Kasei Chemicals Corporation | Elastomer composition and storage cover for airbag system |
| ES2631912T3 (es) * | 2008-04-14 | 2017-09-06 | Asahi Kasei Kabushiki Kaisha | Composición adhesiva |
| WO2009133930A1 (ja) | 2008-04-30 | 2009-11-05 | 旭化成イーマテリアルズ株式会社 | 樹脂組成物及びそれを用いたシート |
| JP5681491B2 (ja) | 2008-12-10 | 2015-03-11 | 旭化成ケミカルズ株式会社 | 熱可塑性エラストマー組成物 |
| JP5599724B2 (ja) | 2008-12-22 | 2014-10-01 | 旭化成ケミカルズ株式会社 | 架橋発泡用組成物、架橋発泡体及びこれを用いた靴用ミッドソール |
| WO2010104174A1 (ja) | 2009-03-12 | 2010-09-16 | 旭化成ケミカルズ株式会社 | ポリプロピレン系樹脂組成物、その成型品及びそれを用いた自動車用内外装材料 |
| ES2423762T3 (es) | 2009-06-22 | 2013-09-24 | Dynasol Elastómeros, S.A. | Catalizador para la hidrogenación de compuestos insaturados |
| JP5705120B2 (ja) | 2009-10-02 | 2015-04-22 | 旭化成ケミカルズ株式会社 | 変性共役ジエン系重合体の製造方法、変性共役ジエン系重合体、及び変性共役ジエン系重合体組成物 |
| CN104262772B (zh) | 2010-03-08 | 2019-01-04 | 旭化成株式会社 | 发泡体用组合物、其制造方法以及发泡体 |
| HUE034394T2 (en) | 2010-04-16 | 2018-02-28 | Asahi Chemical Ind | Process for the preparation of modified conjugated diene polymer, modified conjugated diene polymer and modified conjugated diene polymer composition. |
| CN106977808B (zh) | 2010-06-09 | 2020-07-28 | 三井化学株式会社 | 热塑性弹性体组合物及其成型品 |
| SG2014014575A (en) | 2011-08-26 | 2014-06-27 | Asahi Kasei Chemicals Corp | Method for producing modified conjugated diene polymer, modified conjugated diene polymer, modified conjugated diene polymer composition, rubber composition, rubber composition and tire |
| WO2013161890A1 (ja) | 2012-04-26 | 2013-10-31 | 旭化成ケミカルズ株式会社 | 重合体の製造方法 |
| PL2918614T3 (pl) | 2012-11-06 | 2018-07-31 | Asahi Kasei Kabushiki Kaisha | Sposób wytwarzania polimeru |
| KR102225993B1 (ko) | 2013-02-28 | 2021-03-09 | 제이에스알 가부시끼가이샤 | 타이어용 부재 및 중합체 조성물 |
| WO2014178311A1 (ja) | 2013-04-30 | 2014-11-06 | 旭化成ケミカルズ株式会社 | チタン酸化物含有組成物、重合体組成物、及び成形体 |
| TWI586693B (zh) | 2013-07-23 | 2017-06-11 | 財團法人工業技術研究院 | 選擇性氫化共聚物的方法 |
| KR102185023B1 (ko) | 2013-10-31 | 2020-12-01 | 제이에스알 가부시끼가이샤 | 가교 고무, 타이어용 부재, 방진용 부재, 벨트용 부재 및 고무 조성물 |
| US10472514B2 (en) | 2014-01-23 | 2019-11-12 | Asahi Kasei Kabushiki Kaisha | Block copolymer composition and adhesive composition |
| ES2716377T3 (es) | 2014-06-27 | 2019-06-12 | Kuraray Co | Método para la producción de un polímero hidrogenado |
| EP3351563B1 (en) | 2015-09-14 | 2019-11-06 | JSR Corporation | Method for producing hydrogenated conjugated diene polymer, hydrogenated conjugated diene polymer, polymer composition, cross-linked polymer, and tire |
| WO2018199267A1 (ja) | 2017-04-28 | 2018-11-01 | 旭化成株式会社 | 変性共役ジエン系重合体、重合体組成物、及びゴム組成物 |
| TW201934636A (zh) | 2017-10-25 | 2019-09-01 | 日商Ｊｓｒ股份有限公司 | 聚合體組成物及輪胎 |
| CN110734647B (zh) | 2018-07-20 | 2021-12-17 | 旭化成株式会社 | 热塑性弹性体组合物、栓体和容器 |
| EP3919288A4 (en) | 2019-01-30 | 2022-10-26 | ENEOS Materials Corporation | RUBBER COMPOSITION, NETWORKED BODY AND TIRE |
| TWI829906B (zh) | 2019-03-27 | 2024-01-21 | 日商引能仕材料股份有限公司 | 氫化共軛二烯系聚合物、聚合物組成物、交聯體及輪胎 |
| WO2021054271A1 (ja) | 2019-09-20 | 2021-03-25 | 三井化学株式会社 | 表示装置 |
| JP7697368B2 (ja) | 2019-09-30 | 2025-06-24 | 日本ゼオン株式会社 | 水添ブロック共重合体組成物、その製造方法およびフィルム |
| CN115298859A (zh) | 2020-03-17 | 2022-11-04 | 株式会社引能仕材料 | 全固体二次电池用粘结剂、全固体二次电池用粘结剂组合物、全固体二次电池用浆料、全固体二次电池用固体电解质片及其制造方法、以及全固体二次电池及其制造方法 |
| CN115362578A (zh) | 2020-03-17 | 2022-11-18 | 株式会社引能仕材料 | 全固体二次电池用粘结剂组合物、全固体二次电池用浆料、全固体二次电池用固体电解质片及其制造方法、以及全固体二次电池及其制造方法 |
| WO2021261241A1 (ja) | 2020-06-22 | 2021-12-30 | 旭化成株式会社 | 水添共重合体、樹脂組成物、成形体、及び粘着性フィルム |
| CN113956412A (zh) * | 2020-07-20 | 2022-01-21 | 中国石油天然气股份有限公司 | 氢化苯乙烯类热塑性弹性体及其制备方法 |
| JP7588997B2 (ja) | 2020-09-30 | 2024-11-25 | 株式会社Ｅｎｅｏｓマテリアル | 重合体組成物、架橋体及びタイヤ |
| US20230365795A1 (en) | 2020-10-19 | 2023-11-16 | Zeon Corporation | Resin composition, stretchable film, sheet and tube |
| US20240002643A1 (en) | 2020-11-27 | 2024-01-04 | Eneos Materials Corporation | Polymer composition, cross-linked product, and tire |
| JPWO2022124151A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2020-12-07 | 2022-06-16 | ||
| WO2022163389A1 (ja) | 2021-01-29 | 2022-08-04 | 株式会社Ｅｎｅｏｓマテリアル | 全固体二次電池用バインダー、全固体二次電池用バインダー組成物、全固体二次電池用スラリー、全固体二次電池用固体電解質シート及びその製造方法、並びに全固体二次電池及びその製造方法 |
| JPWO2022163387A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2021-01-29 | 2022-08-04 | ||
| JP7710304B2 (ja) | 2021-03-12 | 2025-07-18 | 株式会社Ｅｎｅｏｓマテリアル | ブロック重合体、重合体組成物及び粘着剤 |
| JP7710305B2 (ja) | 2021-03-12 | 2025-07-18 | 株式会社Ｅｎｅｏｓマテリアル | ブロック共重合体及び粘着剤 |
| CN115703848A (zh) * | 2021-08-04 | 2023-02-17 | 中国石油化工股份有限公司 | 一种氢化丁腈橡胶及其制备方法 |
| EP4382564A4 (en) | 2021-08-06 | 2025-07-23 | Mitsui Chemicals Inc | THERMOPLASTIC ELASTOMER COMPOSITION AND MOLDED BODY MADE THEREOF |
| EP4458892A1 (en) | 2021-12-27 | 2024-11-06 | Zeon Corporation | Foam body and buffer material |
| JPWO2023176810A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2022-03-18 | 2023-09-21 | ||
| CN119487124A (zh) | 2022-07-27 | 2025-02-18 | 日本瑞翁株式会社 | 交联性聚合物组合物、交联物以及交联发泡体 |
| CN120283014A (zh) | 2022-12-07 | 2025-07-08 | 三井化学株式会社 | 热塑性弹性体组合物及由其形成的成型体 |
| KR20250111155A (ko) | 2023-02-21 | 2025-07-22 | 미쯔이가가꾸가부시끼가이샤 | 시트상 표피재 및 당해 표피재를 갖는 적층체 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2005731A1 (de) * | 1969-02-08 | 1970-09-10 | Bridgestone Tire Company Ltd., Tokio | Vulkanisierbare Polymere und Verfahren zu deren Herstellung |
| DE3401983A1 (de) * | 1983-01-20 | 1984-08-02 | Asahi Kasei Kogyo K.K., Osaka | Verfahren zur selektiven hydrierung von polymeren oder copolymeren von konjugierten dienen |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL106564C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1957-06-14 | |||
| US3333024A (en) * | 1963-04-25 | 1967-07-25 | Shell Oil Co | Block polymers, compositions containing them and process of their preparation |
| US3431323A (en) * | 1964-01-20 | 1969-03-04 | Shell Oil Co | Hydrogenated block copolymers of butadiene and a monovinyl aryl hydrocarbon |
| US3595942A (en) * | 1968-12-24 | 1971-07-27 | Shell Oil Co | Partially hydrogenated block copolymers |
| US3700748A (en) * | 1970-05-22 | 1972-10-24 | Shell Oil Co | Selectively hydrogenated block copolymers |
| US3692854A (en) * | 1971-03-22 | 1972-09-19 | Shell Oil Co | Cyclodimerization process |
| US4213879A (en) * | 1979-03-01 | 1980-07-22 | Phillips Petroleum Company | Catalyst composition |
-
1984
- 1984-04-18 JP JP59076614A patent/JPS60220147A/ja active Granted
-
1985
- 1985-04-10 US US06/721,701 patent/US4673714A/en not_active Expired - Lifetime
- 1985-04-16 GB GB08509677A patent/GB2159819B/en not_active Expired
- 1985-04-17 FR FR8505801A patent/FR2565848B1/fr not_active Expired
- 1985-04-18 DE DE19853514063 patent/DE3514063A1/de active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2005731A1 (de) * | 1969-02-08 | 1970-09-10 | Bridgestone Tire Company Ltd., Tokio | Vulkanisierbare Polymere und Verfahren zu deren Herstellung |
| DE3401983A1 (de) * | 1983-01-20 | 1984-08-02 | Asahi Kasei Kogyo K.K., Osaka | Verfahren zur selektiven hydrierung von polymeren oder copolymeren von konjugierten dienen |
| GB2134909A (en) * | 1983-01-20 | 1984-08-22 | Asahi Chemical Ind | Catalytic hydrogenation of conjugated diene polymer |
Non-Patent Citations (3)
| Title |
|---|
| Am. Chem., Bd. 654, 1962, S. 8 * |
| J. Amer. Chem. Soc., Bd. 77, 1955, S. 3604 * |
| J. Organometall. Chem., Bd. 10, 1967, S. 127 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2650964A1 (fr) * | 1988-04-28 | 1991-02-22 | Japan Synthetic Rubber Co Ltd | Catalyseur d'hydrogenation a base de compose du titane et procede d'hydrogenation l'utilisant |
| EP0397026A1 (en) * | 1989-05-09 | 1990-11-14 | The Dow Chemical Company | Process for hydrogenation of polymers |
| AU633564B2 (en) * | 1989-05-09 | 1993-02-04 | Dow Chemical Company, The | Process for hydrogenation of polymers |
| EP0460725A1 (en) * | 1990-05-29 | 1991-12-11 | Shell Internationale Researchmaatschappij B.V. | Selective hydrogenation of conjugated diolefin polymers |
| EP0471415A1 (en) * | 1990-08-15 | 1992-02-19 | Shell Internationale Researchmaatschappij B.V. | Selective hydrogenation of conjugated diolefin polymers |
| EP0544304A1 (en) * | 1991-11-28 | 1993-06-02 | Japan Synthetic Rubber Co., Ltd. | Catalyst composition for hydrogenating olefinically unsaturated polymers |
| EP0545844A1 (en) * | 1991-12-05 | 1993-06-09 | Repsol Quimica S.A. | Process for the hydrogenation of compounds with an olefinic unsaturation |
| WO2018060016A1 (en) * | 2016-09-27 | 2018-04-05 | Basf Se | Star-shaped and triblock polymers with enhanced crosslinkability |
| US11319396B2 (en) | 2016-09-27 | 2022-05-03 | Basf Se | Star-shaped and triblock polymers with enhanced crosslinkability |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2159819B (en) | 1988-08-24 |
| DE3514063C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-12-06 |
| GB2159819A (en) | 1985-12-11 |
| US4673714A (en) | 1987-06-16 |
| JPH0137970B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-08-10 |
| FR2565848A1 (fr) | 1985-12-20 |
| GB8509677D0 (en) | 1985-05-22 |
| JPS60220147A (ja) | 1985-11-02 |
| FR2565848B1 (fr) | 1989-09-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3514063C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE3401983C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2541511C2 (de) | Verfahren zur Herstellung eines Blockcopolymerengemisches | |
| DE2550226C2 (de) | Verzweigte Blockcopolymerisate und Verfahren zu ihrer Herstellung | |
| DE1795766C3 (de) | Thermoplastische Elastomerenmischung auf der Basis von Butadien-Copolymerisaten und Paraffin | |
| EP0026916B1 (de) | Verfahren zur Herstellung von Mischungen linearer Dreiblockcopolymerisate sowie Formteile aus diesen | |
| DE10052183B4 (de) | Katalysatorzusammensetzung zur Hydrierung von Synthesekautschuken auf der Grundlage konjugierter Diene | |
| DE3853600T2 (de) | Selektiv und partiell hydrogeniertes Polymer und Kautschukmischung welche dieses Polymer enthält. | |
| DE60031352T2 (de) | Verfahren zur selektiven Hydrierung von konjugierten Dienpolymeren | |
| DE3880548T2 (de) | Mischungen auf basis von vinylaromatischen polymeren. | |
| DE60107187T2 (de) | Verfahren zur Herstellung eines Dienelastomers durch anionische Polymerisation | |
| DE3040205C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| CH631725A5 (de) | Verfahren zur herstellung von neuen, hydrierten, sternfoermig aufgebauten polymerisaten. | |
| DE60020947T2 (de) | Hydrogenierte block-copolymere | |
| DE3938927C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2449299A1 (de) | Dreiblockpolymeres | |
| DE1245132B (de) | Verfahren zur Herstellung eines elastomeren Blockmischpolymerisats | |
| DE69825184T2 (de) | Verfahren zur hydrierung eines konjugierten dienpolymers | |
| DE69310687T2 (de) | Verfahren zur Hydrierung in Lösung der Doppelbindungen von Polymeren aus conjugiesten Dienen, und hergestellte hydrierte Blockcopolymere | |
| DE3787930T2 (de) | Anionische Polymerisationsverfahren. | |
| EP0312928A1 (de) | Verzweigte Copolymerisate und Verfahren zu ihrer Herstellung | |
| EP0062283B1 (de) | Schlagzähe thermoplastische Formmassen | |
| DE60008229T2 (de) | Hydrogenierte block-copolymere | |
| EP0289917B1 (de) | Butadien-Styrol-Blockcopolymere mit unsymmetrischem Aufbau und deren Herstellung und Verwendung als Formmassen | |
| DE2632235B2 (de) | Verfahren zur Herstellung von schlagzähen Polystyrolen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8128 | New person/name/address of the agent |
Representative=s name: STREHL, P., DIPL.-ING. DIPL.-WIRTSCH.-ING. SCHUEBE |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |