JPH029041B2 - - Google Patents
Info
- Publication number
- JPH029041B2 JPH029041B2 JP4821786A JP4821786A JPH029041B2 JP H029041 B2 JPH029041 B2 JP H029041B2 JP 4821786 A JP4821786 A JP 4821786A JP 4821786 A JP4821786 A JP 4821786A JP H029041 B2 JPH029041 B2 JP H029041B2
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- cyclopentadienyl
- catalyst
- bis
- titanium
- 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.)
- Expired
Links
- 229920000642 polymer Polymers 0.000 claims description 83
- 150000001993 dienes Chemical class 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 27
- -1 bis(cyclopentadienyl) titanium Chemical compound 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 229920001577 copolymer Polymers 0.000 claims description 15
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 12
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical group [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 6
- URXNVXOMQQCBHS-UHFFFAOYSA-N naphthalene;sodium Chemical compound [Na].C1=CC=CC2=CC=CC=C21 URXNVXOMQQCBHS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 229910052701 rubidium Inorganic materials 0.000 claims description 3
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical group [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 125000004436 sodium atom Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 description 67
- 239000003054 catalyst Substances 0.000 description 59
- 230000000694 effects Effects 0.000 description 19
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 239000010936 titanium Substances 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 229920001400 block copolymer Polymers 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 239000000806 elastomer Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 229910052719 titanium Inorganic materials 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 150000002642 lithium compounds Chemical class 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000002736 metal compounds Chemical class 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 229920002725 thermoplastic elastomer Polymers 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CAQWNKXTMBFBGI-UHFFFAOYSA-N C.[Na] Chemical compound C.[Na] CAQWNKXTMBFBGI-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MFRXMZYAKSRDMT-UHFFFAOYSA-L [Br-].[Br-].C1(C=CC=C1)[Ti+2]C1C=CC=C1 Chemical compound [Br-].[Br-].C1(C=CC=C1)[Ti+2]C1C=CC=C1 MFRXMZYAKSRDMT-UHFFFAOYSA-L 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- YMNCCEXICREQQV-UHFFFAOYSA-L cyclopenta-1,3-diene;titanium(4+);dichloride Chemical compound [Cl-].[Cl-].[Ti+4].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 YMNCCEXICREQQV-UHFFFAOYSA-L 0.000 description 3
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 3
- 238000001879 gelation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 150000003112 potassium compounds Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 150000003298 rubidium compounds Chemical class 0.000 description 3
- 150000003388 sodium compounds Chemical class 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-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
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- QJRTWGWWBDOAMP-UHFFFAOYSA-N CC(C)(C)[Na] Chemical compound CC(C)(C)[Na] QJRTWGWWBDOAMP-UHFFFAOYSA-N 0.000 description 2
- HQPSKTOGFFYYKN-UHFFFAOYSA-N CC(C)[Na] Chemical compound CC(C)[Na] HQPSKTOGFFYYKN-UHFFFAOYSA-N 0.000 description 2
- IRDQNLLVRXMERV-UHFFFAOYSA-N CCCC[Na] Chemical compound CCCC[Na] IRDQNLLVRXMERV-UHFFFAOYSA-N 0.000 description 2
- AHCDZZIXAMDCBJ-UHFFFAOYSA-N CCC[Na] Chemical compound CCC[Na] AHCDZZIXAMDCBJ-UHFFFAOYSA-N 0.000 description 2
- NTZRDKVFLPLTPU-UHFFFAOYSA-N CC[Na] Chemical compound CC[Na] NTZRDKVFLPLTPU-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000004073 vulcanization Methods 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
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- QTYUSOHYEPOHLV-FNORWQNLSA-N 1,3-Octadiene Chemical compound CCCC\C=C\C=C QTYUSOHYEPOHLV-FNORWQNLSA-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
- 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
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- HCQUMQYTZHTKDX-UHFFFAOYSA-N C(#CCCCC)[Na] Chemical compound C(#CCCCC)[Na] HCQUMQYTZHTKDX-UHFFFAOYSA-N 0.000 description 1
- PSTURSDOZBUZFT-UHFFFAOYSA-N C1(=CC=CC=C1)CC[Na] Chemical compound C1(=CC=CC=C1)CC[Na] PSTURSDOZBUZFT-UHFFFAOYSA-N 0.000 description 1
- VIKKNRHJFUMVND-UHFFFAOYSA-M C1(C=CC=C1)[Ti](Cl)(OCC)C1C=CC=C1 Chemical compound C1(C=CC=C1)[Ti](Cl)(OCC)C1C=CC=C1 VIKKNRHJFUMVND-UHFFFAOYSA-M 0.000 description 1
- QEPCRAGGRXDAIP-UHFFFAOYSA-N CCC(C)[Na] Chemical compound CCC(C)[Na] QEPCRAGGRXDAIP-UHFFFAOYSA-N 0.000 description 1
- CVZKGBSAERIRCK-UHFFFAOYSA-N CCCCCC[Na] Chemical compound CCCCCC[Na] CVZKGBSAERIRCK-UHFFFAOYSA-N 0.000 description 1
- RWVPJOOMBGGPKS-UHFFFAOYSA-N CCCCC[Na] Chemical compound CCCCC[Na] RWVPJOOMBGGPKS-UHFFFAOYSA-N 0.000 description 1
- CAVXWMJFGMTPEM-UHFFFAOYSA-N CCCCO[Ti](OCCCC)(C1C=CC=C1)C1C=CC=C1 Chemical compound CCCCO[Ti](OCCCC)(C1C=CC=C1)C1C=CC=C1 CAVXWMJFGMTPEM-UHFFFAOYSA-N 0.000 description 1
- LFWLSTNMTRMPLX-UHFFFAOYSA-N CCO[Ti](OCC)(C1C=CC=C1)C1C=CC=C1 Chemical compound CCO[Ti](OCC)(C1C=CC=C1)C1C=CC=C1 LFWLSTNMTRMPLX-UHFFFAOYSA-N 0.000 description 1
- ZPUSJPQMRSWGLL-UHFFFAOYSA-N CC[Cs] Chemical compound CC[Cs] ZPUSJPQMRSWGLL-UHFFFAOYSA-N 0.000 description 1
- ZCUFTCUMEDALHC-UHFFFAOYSA-N CC[K] Chemical compound CC[K] ZCUFTCUMEDALHC-UHFFFAOYSA-N 0.000 description 1
- TUSQWMNASVBZTN-UHFFFAOYSA-N CC[Rb] Chemical compound CC[Rb] TUSQWMNASVBZTN-UHFFFAOYSA-N 0.000 description 1
- CAGJXJQLKVAYGN-UHFFFAOYSA-N CO[Ti](OC)(C1C=CC=C1)C1C=CC=C1 Chemical compound CO[Ti](OC)(C1C=CC=C1)C1C=CC=C1 CAGJXJQLKVAYGN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- HIGZGRCLEZNBMJ-UHFFFAOYSA-L O(c1ccccc1)[Ti](Oc1ccccc1)(C1C=CC=C1)C1C=CC=C1 Chemical compound O(c1ccccc1)[Ti](Oc1ccccc1)(C1C=CC=C1)C1C=CC=C1 HIGZGRCLEZNBMJ-UHFFFAOYSA-L 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- PEUDOSQDHLQVIA-UHFFFAOYSA-L [Br-].[Br-].C1(C=CC=C1)[Zr+2]C1C=CC=C1 Chemical compound [Br-].[Br-].C1(C=CC=C1)[Zr+2]C1C=CC=C1 PEUDOSQDHLQVIA-UHFFFAOYSA-L 0.000 description 1
- HLZIGZQAUDKTBR-UHFFFAOYSA-N [Cs]CC1=CC=CC=C1 Chemical compound [Cs]CC1=CC=CC=C1 HLZIGZQAUDKTBR-UHFFFAOYSA-N 0.000 description 1
- DWRANCXBXXRLPN-UHFFFAOYSA-L [O-]C1=CC=CC=C1.[Cl-].[Ti+2] Chemical compound [O-]C1=CC=CC=C1.[Cl-].[Ti+2] DWRANCXBXXRLPN-UHFFFAOYSA-L 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000012718 coordination polymerization Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- WDGICGVEWQIMTQ-UHFFFAOYSA-L cyclopentane;difluorotitanium Chemical compound F[Ti]F.[CH]1[CH][CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1 WDGICGVEWQIMTQ-UHFFFAOYSA-L 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000004989 dicarbonyl group Chemical group 0.000 description 1
- XXLOICMXOBKOLH-UHFFFAOYSA-L diiodotitanium Chemical compound I[Ti]I XXLOICMXOBKOLH-UHFFFAOYSA-L 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- CCZVEWRRAVASGL-UHFFFAOYSA-N lithium;2-methanidylpropane Chemical compound [Li+].CC(C)[CH2-] CCZVEWRRAVASGL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 description 1
- XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- BHGADZKHWXCHKX-UHFFFAOYSA-N methane;potassium Chemical compound C.[K] BHGADZKHWXCHKX-UHFFFAOYSA-N 0.000 description 1
- WWUXUITYSVCHKK-UHFFFAOYSA-N methanidylbenzene;rubidium(1+) Chemical compound [Rb+].[CH2-]C1=CC=CC=C1 WWUXUITYSVCHKK-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 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
- 239000003921 oil Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920000636 poly(norbornene) polymer Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- FZWIBIHTJMCHGT-UHFFFAOYSA-N potassium;diphenylmethylbenzene Chemical compound [K+].C1=CC=CC=C1[C-](C=1C=CC=CC=1)C1=CC=CC=C1 FZWIBIHTJMCHGT-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 description 1
- OHUVHDUNQKJDKW-UHFFFAOYSA-N sodium;cyclopenta-1,3-diene Chemical compound [Na+].C=1C=C[CH-]C=1 OHUVHDUNQKJDKW-UHFFFAOYSA-N 0.000 description 1
- UJTRRNALUYKHQE-UHFFFAOYSA-N sodium;diphenylmethylbenzene Chemical compound [Na+].C1=CC=CC=C1[C-](C=1C=CC=CC=1)C1=CC=CC=C1 UJTRRNALUYKHQE-UHFFFAOYSA-N 0.000 description 1
- OWMHBKYAOYHOQK-UHFFFAOYSA-N sodium;methanidylbenzene Chemical compound [Na+].[CH2-]C1=CC=CC=C1 OWMHBKYAOYHOQK-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Landscapes
- Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4821786A JPS62207303A (ja) | 1986-03-07 | 1986-03-07 | 共役ジエン系ポリマ−の水添法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4821786A JPS62207303A (ja) | 1986-03-07 | 1986-03-07 | 共役ジエン系ポリマ−の水添法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62207303A JPS62207303A (ja) | 1987-09-11 |
| JPH029041B2 true JPH029041B2 (US07642317-20100105-C00018.png) | 1990-02-28 |
Family
ID=12797244
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4821786A Granted JPS62207303A (ja) | 1986-03-07 | 1986-03-07 | 共役ジエン系ポリマ−の水添法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62207303A (US07642317-20100105-C00018.png) |
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6875827B2 (en) | 2001-04-11 | 2005-04-05 | Asahi Kasei Kabushiki Kaisha | Hydrogenated polymer and process for producing the same |
| WO2006123670A1 (ja) | 2005-05-19 | 2006-11-23 | Mitsui Chemicals, Inc. | 発泡体用樹脂組成物およびその用途 |
| US7256238B2 (en) | 2001-07-18 | 2007-08-14 | Asahi Kasei Chemicals Corporation | Modified block copolymer |
| WO2008013090A1 (fr) | 2006-07-24 | 2008-01-31 | Asahi Kasei Chemicals Corporation | Polymère de diène conjugué modifié et procédé de production de celui-ci |
| WO2008018445A1 (fr) | 2006-08-08 | 2008-02-14 | Asahi Kasei Chemicals Corporation | Copolymères séquencés hydrogénés et compositions de réticulation les contenant |
| WO2008102761A1 (ja) | 2007-02-20 | 2008-08-28 | Asahi Kasei Chemicals Corporation | 衝撃吸収体組成物 |
| 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 |
| WO2011155571A1 (ja) | 2010-06-09 | 2011-12-15 | 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及びその成形品 |
| 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 |
| WO2013031599A1 (ja) | 2011-08-26 | 2013-03-07 | 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、変性共役ジエン系重合体組成物、ゴム組成物、及びタイヤ |
| US8653176B2 (en) | 2006-12-26 | 2014-02-18 | Asahi Kasei E-Materials Corporation | Thermally conductive material and thermally conductive sheet molded from the thermally conductive material |
| EP2700658A1 (en) | 2010-04-16 | 2014-02-26 | Asahi Kasei Chemicals Corporation | Process for producing modified conjugated diene polymer, modified conjugated diene polymer, and composition of modified conjugated diene polymer |
| US8816014B2 (en) | 2009-10-02 | 2014-08-26 | Asahi Kasei Chemicals Corporation | Method for producing modified conjugated diene-based polymer, modified conjugated diene-based polymer, and modified conjugated diene-based polymer composition |
| WO2015108150A1 (ja) | 2014-01-17 | 2015-07-23 | 旭化成ケミカルズ株式会社 | 重合体及びアスファルト組成物 |
| WO2015108139A1 (ja) | 2014-01-17 | 2015-07-23 | 旭化成ケミカルズ株式会社 | 重合体及びアスファルト組成物 |
| WO2015111669A1 (ja) | 2014-01-23 | 2015-07-30 | 旭化成ケミカルズ株式会社 | ブロック共重合体組成物及び粘接着剤組成物 |
| 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 |
| US10179850B2 (en) | 2010-03-08 | 2019-01-15 | Asahi Kasei Chemicals Corporation | Foamable composition, process for producing the same and foam |
| DE102019119630A1 (de) | 2018-07-20 | 2020-01-23 | Asahi Kasei Kabushiki Kaisha | Thermoplastische Elastomerzusammensetzung, Stopfen und Behälter |
| WO2021054271A1 (ja) | 2019-09-20 | 2021-03-25 | 三井化学株式会社 | 表示装置 |
| WO2023013772A1 (ja) | 2021-08-06 | 2023-02-09 | 三井化学株式会社 | 熱可塑性エラストマー組成物およびこれからなる成形体 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP2258771B1 (en) | 2008-03-25 | 2012-10-31 | Asahi Kasei Chemicals Corporation | Elastomer composition and storage cover for airbag system |
| US9139722B2 (en) | 2009-03-12 | 2015-09-22 | Asahi Kasei Chemicals Corporation | Polypropylene-based resin composition, molded article thereof, and automobile interior or exterior material using the same |
-
1986
- 1986-03-07 JP JP4821786A patent/JPS62207303A/ja active Granted
Cited By (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6875827B2 (en) | 2001-04-11 | 2005-04-05 | Asahi Kasei Kabushiki Kaisha | Hydrogenated polymer and process for producing the same |
| US7256238B2 (en) | 2001-07-18 | 2007-08-14 | Asahi Kasei Chemicals Corporation | Modified block copolymer |
| US7414093B2 (en) | 2001-07-18 | 2008-08-19 | Asahi Kasei Chemicals Corporation | Modified block copolymer |
| US7642317B2 (en) | 2001-07-18 | 2010-01-05 | Asahi Kasei Chemicals Corporation | Modified block copolymer |
| US7642318B2 (en) | 2001-07-18 | 2010-01-05 | Asahi Kasei Chemicals Corporation | Modified block copolymer |
| WO2006123670A1 (ja) | 2005-05-19 | 2006-11-23 | Mitsui Chemicals, Inc. | 発泡体用樹脂組成物およびその用途 |
| US8772365B2 (en) | 2005-05-19 | 2014-07-08 | Mitsui Chemicals, Inc. | Resin composition for foams and uses thereof |
| US8106130B2 (en) | 2006-07-24 | 2012-01-31 | Asahi Kasei Chemicals Corporation | Modified conjugated diene polymer and process for producing thereof |
| WO2008013090A1 (fr) | 2006-07-24 | 2008-01-31 | Asahi Kasei Chemicals Corporation | Polymère de diène conjugué modifié et procédé de production de celui-ci |
| WO2008018445A1 (fr) | 2006-08-08 | 2008-02-14 | Asahi Kasei Chemicals Corporation | Copolymères séquencés hydrogénés et compositions de réticulation les contenant |
| EP2230265A1 (en) | 2006-08-08 | 2010-09-22 | Asahi Kasei Chemicals Corporation | Hydrogenated block copolymers and crosslinking compositions containing the same |
| US8653176B2 (en) | 2006-12-26 | 2014-02-18 | Asahi Kasei E-Materials Corporation | Thermally conductive material and thermally conductive sheet molded from the thermally conductive material |
| WO2008102761A1 (ja) | 2007-02-20 | 2008-08-28 | Asahi Kasei Chemicals Corporation | 衝撃吸収体組成物 |
| US8541504B2 (en) | 2007-02-20 | 2013-09-24 | Asahi Kasei Chemicals Corporation | Impact absorber composition |
| 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 |
| 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 |
| US8816014B2 (en) | 2009-10-02 | 2014-08-26 | Asahi Kasei Chemicals Corporation | Method for producing modified conjugated diene-based polymer, modified conjugated diene-based polymer, and modified conjugated diene-based polymer composition |
| US10179850B2 (en) | 2010-03-08 | 2019-01-15 | Asahi Kasei Chemicals Corporation | Foamable composition, process for producing the same and foam |
| EP2700658A1 (en) | 2010-04-16 | 2014-02-26 | Asahi Kasei Chemicals Corporation | Process for producing modified conjugated diene polymer, modified conjugated diene polymer, and composition of modified conjugated diene polymer |
| US9193807B2 (en) | 2010-04-16 | 2015-11-24 | Asahi Kasei Chemicals Corporation | Method for producing modified conjugated diene-based polymer, modified conjugated diene-based polymer, and modified conjugated diene-based polymer composition |
| US9644046B2 (en) | 2010-04-16 | 2017-05-09 | Asahi Kasei Chemicals Corporation | Method for producing modified conjugated diene-based polymer, modified conjugated diene-based polymer, and modified conjugated diene-based polymer composition |
| WO2011155571A1 (ja) | 2010-06-09 | 2011-12-15 | 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及びその成形品 |
| US9096748B2 (en) | 2010-06-09 | 2015-08-04 | Asahi Kasei Chemicals Corporation | Thermoplastic elastomer composition and molded products using the same |
| WO2013031599A1 (ja) | 2011-08-26 | 2013-03-07 | 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、変性共役ジエン系重合体組成物、ゴム組成物、及びタイヤ |
| WO2015108150A1 (ja) | 2014-01-17 | 2015-07-23 | 旭化成ケミカルズ株式会社 | 重合体及びアスファルト組成物 |
| WO2015108139A1 (ja) | 2014-01-17 | 2015-07-23 | 旭化成ケミカルズ株式会社 | 重合体及びアスファルト組成物 |
| WO2015111669A1 (ja) | 2014-01-23 | 2015-07-30 | 旭化成ケミカルズ株式会社 | ブロック共重合体組成物及び粘接着剤組成物 |
| 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 |
| DE102019119630A1 (de) | 2018-07-20 | 2020-01-23 | Asahi Kasei Kabushiki Kaisha | Thermoplastische Elastomerzusammensetzung, Stopfen und Behälter |
| DE102019119630B4 (de) | 2018-07-20 | 2024-02-29 | Asahi Kasei Kabushiki Kaisha | Thermoplastische Elastomerzusammensetzung, deren Verwendung, Stopfen und Behälter |
| WO2021054271A1 (ja) | 2019-09-20 | 2021-03-25 | 三井化学株式会社 | 表示装置 |
| WO2023013772A1 (ja) | 2021-08-06 | 2023-02-09 | 三井化学株式会社 | 熱可塑性エラストマー組成物およびこれからなる成形体 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62207303A (ja) | 1987-09-11 |
Similar Documents
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |