JPS634841B2 - - Google Patents

Info

Publication number: JPS634841B2
Authority: JP; Japan
Prior art keywords: polymer; hydrogenation; conjugated diene; catalyst; styrene
Prior art date: 1983-01-20
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

Application number

JP671883A

Other languages

English (en)

Japanese (ja)

Other versions

JPS59133203A (ja

Inventor

Yasushi Kishimoto

Hideo Morita

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Asahi Chemical Industry Co Ltd

Original Assignee

Asahi Chemical Industry Co Ltd

Priority date (The priority date 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 date listed.)

1983-01-20

Filing date

1983-01-20

Publication date

1988-02-01

1983-01-20 Application filed by Asahi Chemical Industry Co Ltd filed Critical Asahi Chemical Industry Co Ltd

1983-01-20 Priority to JP671883A priority Critical patent/JPS59133203A/ja

1984-01-06 Priority to US06/568,692 priority patent/US4501857A/en

1984-01-06 Priority to GB08400305A priority patent/GB2134909B/en

1984-01-19 Priority to FR8400820A priority patent/FR2539745B1/fr

1984-01-20 Priority to DE3448317A priority patent/DE3448317C2/de

1984-01-20 Priority to DE19843401983 priority patent/DE3401983A1/de

1984-07-31 Publication of JPS59133203A publication Critical patent/JPS59133203A/ja

1988-02-01 Publication of JPS634841B2 publication Critical patent/JPS634841B2/ja

Status Granted legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 claims description 144
238000005984 hydrogenation reaction Methods 0.000 claims description 125
239000003054 catalyst Substances 0.000 claims description 93
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 51
150000001993 dienes Chemical class 0.000 claims description 46
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 40
229920001577 copolymer Polymers 0.000 claims description 34
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 30
238000000034 method Methods 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 18
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 5
230000000379 polymerizing effect Effects 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
125000002029 aromatic hydrocarbon group Chemical class 0.000 claims 1
JAGHDVYKBYUAFD-UHFFFAOYSA-L cyclopenta-1,3-diene;titanium(4+);dichloride Chemical compound [Cl-].[Cl-].[Ti+4].C1C=CC=[C-]1.C1C=CC=[C-]1 JAGHDVYKBYUAFD-UHFFFAOYSA-L 0.000 claims 1
125000002897 diene group Chemical group 0.000 description 34
230000000694 effects Effects 0.000 description 26
125000003118 aryl group Chemical group 0.000 description 23
229920001400 block copolymer Polymers 0.000 description 19
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
229920002554 vinyl polymer Polymers 0.000 description 17
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 15
239000000178 monomer Substances 0.000 description 14
239000002904 solvent Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
KSFCHHFBQJDGFF-UHFFFAOYSA-L cyclopenta-1,3-diene;dichlorotitanium Chemical compound Cl[Ti]Cl.C1C=CC=C1.C1C=CC=C1 KSFCHHFBQJDGFF-UHFFFAOYSA-L 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
238000000862 absorption spectrum Methods 0.000 description 7
-1 carbon Chemical class 0.000 description 7
238000006116 polymerization reaction Methods 0.000 description 7
239000012298 atmosphere Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
230000003647 oxidation Effects 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
239000010936 titanium Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
150000001336 alkenes Chemical class 0.000 description 5
239000002815 homogeneous catalyst Substances 0.000 description 5
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
229920002725 thermoplastic elastomer Polymers 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
238000001879 gelation Methods 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 4
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical group CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
229920001971 elastomer Polymers 0.000 description 3
239000002638 heterogeneous catalyst Substances 0.000 description 3
229920001519 homopolymer Polymers 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
229910052759 nickel Inorganic materials 0.000 description 3
230000000704 physical effect Effects 0.000 description 3
229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
229920005992 thermoplastic resin Polymers 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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
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 2
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000007423 decrease Effects 0.000 description 2
239000000806 elastomer Substances 0.000 description 2
229920000578 graft copolymer Polymers 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002156 mixing Methods 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
150000002900 organolithium compounds Chemical class 0.000 description 2
150000002902 organometallic compounds Chemical class 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
229920005604 random copolymer Polymers 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
229910052719 titanium Inorganic materials 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
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
ZBFBXTFQCKIUHU-UHFFFAOYSA-L 1,2,3,5,5-pentamethylcyclopenta-1,3-diene;titanium(4+);dichloride Chemical compound [Cl-].[Cl-].[Ti+4].CC1=[C-]C(C)(C)C(C)=C1C.CC1=[C-]C(C)(C)C(C)=C1C ZBFBXTFQCKIUHU-UHFFFAOYSA-L 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
ROGIWVXWXZRRMZ-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1 ROGIWVXWXZRRMZ-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
VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
KKDBZWZRJNRBGA-UHFFFAOYSA-L Cl[Ti]Cl.[CH]1C=CC=C1 Chemical compound Cl[Ti]Cl.[CH]1C=CC=C1 KKDBZWZRJNRBGA-UHFFFAOYSA-L 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 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
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
239000002174 Styrene-butadiene Substances 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
IPTJKFGGRLMTIC-UHFFFAOYSA-L [I-].[I-].C1(C=CC=C1)[Ti+2]C1C=CC=C1 Chemical compound [I-].[I-].C1(C=CC=C1)[Ti+2]C1C=CC=C1 IPTJKFGGRLMTIC-UHFFFAOYSA-L 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical class CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000654 additive Substances 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
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
230000015572 biosynthetic process Effects 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000010538 cationic polymerization reaction Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
238000004581 coalescence Methods 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
238000011437 continuous method Methods 0.000 description 1
238000012718 coordination polymerization Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
QOXHZZQZTIGPEV-UHFFFAOYSA-K cyclopenta-1,3-diene;titanium(4+);trichloride Chemical compound Cl[Ti+](Cl)Cl.C=1C=C[CH-]C=1 QOXHZZQZTIGPEV-UHFFFAOYSA-K 0.000 description 1
SRKKQWSERFMTOX-UHFFFAOYSA-N cyclopentane;titanium Chemical class [Ti].[CH]1C=CC=C1 SRKKQWSERFMTOX-UHFFFAOYSA-N 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
238000004821 distillation Methods 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
230000001747 exhibiting effect Effects 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
238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 1
XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-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
150000002739 metals Chemical class 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 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
BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000002899 organoaluminium compounds Chemical class 0.000 description 1
150000002901 organomagnesium compounds Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
229920005672 polyolefin resin Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000005060 rubber Substances 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
239000005049 silicon tetrachloride Substances 0.000 description 1
239000011115 styrene butadiene Substances 0.000 description 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
150000003609 titanium compounds Chemical class 0.000 description 1
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 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
239000008096 xylene Substances 0.000 description 1

Landscapes

Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

JP671883A 1983-01-20 1983-01-20 重合体の水添方法 Granted JPS59133203A (ja)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
JP671883A JPS59133203A (ja)	1983-01-20	1983-01-20	重合体の水添方法
US06/568,692 US4501857A (en)	1983-01-20	1984-01-06	Method for hydrogenation of polymer
GB08400305A GB2134909B (en)	1983-01-20	1984-01-06	Catalytic hydrogenation of conjugated diene polymer
FR8400820A FR2539745B1 (fr)	1983-01-20	1984-01-19	Procede d'hydrogenation d'un polymere diene conjugue
DE3448317A DE3448317C2 (ru)	1983-01-20	1984-01-20
DE19843401983 DE3401983A1 (de)	1983-01-20	1984-01-20	Verfahren zur selektiven hydrierung von polymeren oder copolymeren von konjugierten dienen

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP671883A JPS59133203A (ja)	1983-01-20	1983-01-20	重合体の水添方法

Publications (2)

Publication Number	Publication Date
JPS59133203A JPS59133203A (ja)	1984-07-31
JPS634841B2 true JPS634841B2 (ru)	1988-02-01

Family

ID=11646040

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP671883A Granted JPS59133203A (ja)	1983-01-20	1983-01-20	重合体の水添方法

Country Status (1)

Country	Link
JP (1)	JPS59133203A (ru)

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1983
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Also Published As

Publication number	Publication date
JPS59133203A (ja)	1984-07-31

Publication	Publication Date	Title
JPS634841B2 (ru)	1988-02-01
JP2718059B2 (ja)	1998-02-25	重合体の水素添加方法および触媒
JP3166137B2 (ja)	2001-05-14	オレフィン性不飽和重合体の水素化方法および水素添加触媒
JP2783791B2 (ja)	1998-08-06	共役ジエンポリマーの選択的水素化方法
JPH0137970B2 (ru)	1989-08-10
JP3326772B2 (ja)	2002-09-24	オレフィン性不飽和重合体の水素化方法および水素添加触媒
JP3484155B2 (ja)	2004-01-06	共役ジエンを含む重合体の選択的水素化方法
JPS635401B2 (ru)	1988-02-03
KR100201228B1 (ko)	1999-06-15	리빙중합체의 수첨방법
JP3227678B2 (ja)	2001-11-12	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触媒
JPH0153851B2 (ru)	1989-11-15
JPH029041B2 (ru)	1990-02-28
JPH0116401B2 (ru)	1989-03-24
JPH029043B2 (ru)	1990-02-28
JPH05286870A (ja)	1993-11-02	オレフィンの水素添加法
US5910566A (en)	1999-06-08	Living polymer hydrogenation catalyst and process for hydrogenating polymers with the catalyst
JPH029042B2 (ru)	1990-02-28
JPS635402B2 (ru)	1988-02-03
JPH0496904A (ja)	1992-03-30	オレフィン化合物の水添法
JPH02311504A (ja)	1990-12-27	ポリマーの水素化法
JP2903471B1 (ja)	1999-06-07	共役ジエン重合体の水素化方法
JP3454922B2 (ja)	2003-10-06	イソプレン系重合体の水添方法
JP2609534B2 (ja)	1997-05-14	オレフィン性不飽和ポリマーの水添方法
JP3651931B2 (ja)	2005-05-25	アルキル基置換共役ジエン重合体の水添法
JP3282166B2 (ja)	2002-05-13	オレフィン性不飽和重合体の水素化方法および水素添加触媒