CA1166400A - Polymerisation en solution - Google Patents

Polymerisation en solution

Info

Publication number: CA1166400A
Authority: CA; Canada
Prior art keywords: alcoholate; trans; magnesium; catalyst; butadiene
Prior art date: 1980-02-25
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

CA000353683A

Other languages

English (en)

Inventor

Robert E. Bingham

Sundar L. Aggarwal

Richard R. Durst

Hubert J. Fabris

Russell A. Livigni

Ivan G. Hargis

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.)

Omnova Solutions Inc

Original Assignee

General Tire and Rubber Co

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.)

1980-02-25

Filing date

1980-06-10

Publication date

1984-04-24

1980-02-25 Priority claimed from US06/124,373 external-priority patent/US4302568A/en

1980-06-10 Application filed by General Tire and Rubber Co filed Critical General Tire and Rubber Co

1984-04-24 Application granted granted Critical

1984-04-24 Publication of CA1166400A publication Critical patent/CA1166400A/fr

Status Expired legal-status Critical Current

Links

238000010528 free radical solution polymerization reaction Methods 0.000 title abstract description 7
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 108
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 100
239000003054 catalyst Substances 0.000 claims abstract description 92
239000000203 mixture Substances 0.000 claims abstract description 92
229920000642 polymer Polymers 0.000 claims abstract description 79
239000000178 monomer Substances 0.000 claims abstract description 60
229910052788 barium Inorganic materials 0.000 claims abstract description 53
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims abstract description 42
150000001875 compounds Chemical class 0.000 claims abstract description 37
229920001577 copolymer Polymers 0.000 claims abstract description 37
239000011575 calcium Substances 0.000 claims abstract description 28
229910052791 calcium Inorganic materials 0.000 claims abstract description 27
229910052712 strontium Inorganic materials 0.000 claims abstract description 24
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 15
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims abstract description 15
150000002901 organomagnesium compounds Chemical class 0.000 claims abstract description 13
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 11
239000011777 magnesium Substances 0.000 claims description 83
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 60
229910052749 magnesium Inorganic materials 0.000 claims description 38
239000002904 solvent Substances 0.000 claims description 38
229920002554 vinyl polymer Polymers 0.000 claims description 38
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 36
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 34
238000000034 method Methods 0.000 claims description 34
238000006243 chemical reaction Methods 0.000 claims description 30
125000000217 alkyl group Chemical group 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 22
229910001868 water Inorganic materials 0.000 claims description 22
229910052751 metal Inorganic materials 0.000 claims description 21
239000002184 metal Substances 0.000 claims description 21
229910052782 aluminium Inorganic materials 0.000 claims description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
239000004215 Carbon black (E152) Substances 0.000 claims description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 15
229930195733 hydrocarbon Natural products 0.000 claims description 15
238000002844 melting Methods 0.000 claims description 15
230000008018 melting Effects 0.000 claims description 15
238000004455 differential thermal analysis Methods 0.000 claims description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
150000002430 hydrocarbons Chemical class 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
230000000379 polymerizing effect Effects 0.000 claims description 9
239000000047 product Substances 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 6
150000001336 alkenes Chemical class 0.000 claims description 5
238000010539 anionic addition polymerization reaction Methods 0.000 claims description 5
230000001747 exhibiting effect Effects 0.000 claims description 5
239000002685 polymerization catalyst Substances 0.000 claims description 5
238000002441 X-ray diffraction Methods 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 3
230000009477 glass transition Effects 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
125000002734 organomagnesium group Chemical group 0.000 claims description 2
230000002829 reductive effect Effects 0.000 claims description 2
125000003158 alcohol group Chemical group 0.000 claims 4
229920006395 saturated elastomer Polymers 0.000 claims 1
238000001291 vacuum drying Methods 0.000 claims 1
238000006116 polymerization reaction Methods 0.000 abstract description 76
-1 siloxanes Chemical class 0.000 abstract description 43
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract description 22
238000002360 preparation method Methods 0.000 abstract description 17
150000003951 lactams Chemical class 0.000 abstract description 4
150000002924 oxiranes Chemical class 0.000 abstract description 4
150000003553 thiiranes Chemical class 0.000 abstract description 4
229920003048 styrene butadiene rubber Polymers 0.000 description 59
239000002174 Styrene-butadiene Substances 0.000 description 54
229920002857 polybutadiene Polymers 0.000 description 46
229920001971 elastomer Polymers 0.000 description 43
239000005060 rubber Substances 0.000 description 39
239000005062 Polybutadiene Substances 0.000 description 33
239000000243 solution Substances 0.000 description 26
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
244000043261 Hevea brasiliensis Species 0.000 description 21
229920003052 natural elastomer Polymers 0.000 description 21
229920001194 natural rubber Polymers 0.000 description 21
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 20
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 20
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
159000000009 barium salts Chemical class 0.000 description 17
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 16
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
230000000694 effects Effects 0.000 description 14
235000001465 calcium Nutrition 0.000 description 11
229960005069 calcium Drugs 0.000 description 11
150000001993 dienes Chemical class 0.000 description 11
239000007788 liquid Substances 0.000 description 11
229910003023 Mg-Al Inorganic materials 0.000 description 10
239000003921 oil Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000004793 Polystyrene Substances 0.000 description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
230000007423 decrease Effects 0.000 description 8
239000000463 material Substances 0.000 description 8
229920003194 trans-1,4-polybutadiene polymer Polymers 0.000 description 8
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 8
239000006229 carbon black Substances 0.000 description 7
238000007334 copolymerization reaction Methods 0.000 description 7
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
229920000359 diblock copolymer Polymers 0.000 description 7
239000000839 emulsion Substances 0.000 description 7
229920002223 polystyrene Polymers 0.000 description 7
229910052717 sulfur Inorganic materials 0.000 description 7
239000011593 sulfur Substances 0.000 description 7
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
239000003963 antioxidant agent Substances 0.000 description 6
235000006708 antioxidants Nutrition 0.000 description 6
230000003247 decreasing effect Effects 0.000 description 6
238000009826 distribution Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
230000003078 antioxidant effect Effects 0.000 description 5
230000000875 corresponding effect Effects 0.000 description 5
YHNWUQFTJNJVNU-UHFFFAOYSA-N magnesium;butane;ethane Chemical compound [Mg+2].[CH2-]C.CCC[CH2-] YHNWUQFTJNJVNU-UHFFFAOYSA-N 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
239000004970 Chain extender Substances 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
150000002118 epoxides Chemical class 0.000 description 4
239000000945 filler Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000003999 initiator Substances 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
239000002808 molecular sieve Substances 0.000 description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 3
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
235000021355 Stearic acid Nutrition 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
238000005299 abrasion Methods 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
230000001419 dependent effect Effects 0.000 description 3
125000002897 diene group Chemical group 0.000 description 3
239000000806 elastomer Substances 0.000 description 3
229920006158 high molecular weight polymer Polymers 0.000 description 3
238000010348 incorporation Methods 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
230000000670 limiting effect Effects 0.000 description 3
229910000069 nitrogen hydride Inorganic materials 0.000 description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
150000002902 organometallic compounds Chemical class 0.000 description 3
229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 3
239000002243 precursor Substances 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000008117 stearic acid Substances 0.000 description 3
150000003509 tertiary alcohols Chemical class 0.000 description 3
238000012360 testing method Methods 0.000 description 3
229920001169 thermoplastic Polymers 0.000 description 3
238000012546 transfer Methods 0.000 description 3
BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 2
FRDAATYAJDYRNW-UHFFFAOYSA-N 3-methyl-3-pentanol Chemical compound CCC(C)(O)CC FRDAATYAJDYRNW-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
229910018134 Al-Mg Inorganic materials 0.000 description 2
229910018467 Al—Mg Inorganic materials 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
238000013459 approach Methods 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
SLPLCLDJTNLWPW-UHFFFAOYSA-N barium(2+);2-methylpropan-2-olate Chemical compound [Ba+2].CC(C)(C)[O-].CC(C)(C)[O-] SLPLCLDJTNLWPW-UHFFFAOYSA-N 0.000 description 2
SBMJKCDBJMFHGS-UHFFFAOYSA-L barium(2+);2-nonylphenolate Chemical compound [Ba+2].CCCCCCCCCC1=CC=CC=C1[O-].CCCCCCCCCC1=CC=CC=C1[O-] SBMJKCDBJMFHGS-UHFFFAOYSA-L 0.000 description 2
GYIWFHXWLCXGQO-UHFFFAOYSA-N barium(2+);ethanolate Chemical compound [Ba+2].CC[O-].CC[O-] GYIWFHXWLCXGQO-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 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
OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000010276 construction Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
229920001519 homopolymer Polymers 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
KJJBSBKRXUVBMX-UHFFFAOYSA-N magnesium;butane Chemical compound [Mg+2].CCC[CH2-].CCC[CH2-] KJJBSBKRXUVBMX-UHFFFAOYSA-N 0.000 description 2
238000005259 measurement Methods 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
150000002900 organolithium compounds Chemical class 0.000 description 2
125000001979 organolithium group Chemical group 0.000 description 2
125000002524 organometallic group Chemical group 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920001228 polyisocyanate Polymers 0.000 description 2
239000005056 polyisocyanate Substances 0.000 description 2
UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
238000012545 processing Methods 0.000 description 2
ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
230000005855 radiation Effects 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229920003051 synthetic elastomer Polymers 0.000 description 2
239000005061 synthetic rubber Substances 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
239000004416 thermosoftening plastic Substances 0.000 description 2
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 2
239000003643 water by type Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
239000011787 zinc oxide Substances 0.000 description 2
UHBYWEGGFUCNJL-UHFFFAOYSA-N 1,1-dicyclohexylbutan-1-ol Chemical compound C1CCCCC1C(O)(CCC)C1CCCCC1 UHBYWEGGFUCNJL-UHFFFAOYSA-N 0.000 description 1
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229910021645 metal ion Inorganic materials 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000000465 moulding Methods 0.000 description 1
UCAOGXRUJFKQAP-UHFFFAOYSA-N n,n-dimethyl-5-nitropyridin-2-amine Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C=N1 UCAOGXRUJFKQAP-UHFFFAOYSA-N 0.000 description 1
DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052754 neon Inorganic materials 0.000 description 1
GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
229940065472 octyl acrylate Drugs 0.000 description 1
ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000012285 osmium tetroxide Substances 0.000 description 1
229910000489 osmium tetroxide Inorganic materials 0.000 description 1
238000002103 osmometry Methods 0.000 description 1
238000010525 oxidative degradation reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
150000002932 p-cymene derivatives Chemical class 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920001084 poly(chloroprene) Polymers 0.000 description 1
229920001195 polyisoprene Polymers 0.000 description 1
229920006254 polymer film Polymers 0.000 description 1
230000037048 polymerization activity Effects 0.000 description 1
229920003246 polypentenamer Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920003225 polyurethane elastomer Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011253 protective coating Substances 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000005049 silicon tetrachloride Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
238000003860 storage Methods 0.000 description 1
SGAOTOMUHFNBAR-UHFFFAOYSA-N strontium;2-methylpropan-2-olate Chemical compound [Sr+2].CC(C)(C)[O-].CC(C)(C)[O-] SGAOTOMUHFNBAR-UHFFFAOYSA-N 0.000 description 1
238000012916 structural analysis Methods 0.000 description 1
239000011115 styrene butadiene Substances 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229920001897 terpolymer Polymers 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000010512 thermal transition Effects 0.000 description 1
238000001757 thermogravimetry curve Methods 0.000 description 1
XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
150000007944 thiolates Chemical class 0.000 description 1
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
150000003623 transition metal compounds Chemical class 0.000 description 1
SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
ZIYNWDQDHKSRCE-UHFFFAOYSA-N tricyclohexylalumane Chemical compound C1CCCCC1[Al](C1CCCCC1)C1CCCCC1 ZIYNWDQDHKSRCE-UHFFFAOYSA-N 0.000 description 1
MRGVKQSSSOCONZ-UHFFFAOYSA-N tricyclohexylmethanol Chemical compound C1CCCCC1C(C1CCCCC1)(O)C1CCCCC1 MRGVKQSSSOCONZ-UHFFFAOYSA-N 0.000 description 1
PYLGJXLKFZZEBJ-UHFFFAOYSA-N tricyclopentylalumane Chemical compound C1CCCC1[Al](C1CCCC1)C1CCCC1 PYLGJXLKFZZEBJ-UHFFFAOYSA-N 0.000 description 1
XBEXIHMRFRFRAM-UHFFFAOYSA-N tridodecylalumane Chemical compound CCCCCCCCCCCC[Al](CCCCCCCCCCCC)CCCCCCCCCCCC XBEXIHMRFRFRAM-UHFFFAOYSA-N 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-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
150000005199 trimethylbenzenes Chemical class 0.000 description 1
LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
JOJQVUCWSDRWJE-UHFFFAOYSA-N tripentylalumane Chemical compound CCCCC[Al](CCCCC)CCCCC JOJQVUCWSDRWJE-UHFFFAOYSA-N 0.000 description 1
CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
NTKCNHURDVTMQK-UHFFFAOYSA-N tris(2,2,4-trimethylpentyl)alumane Chemical compound CC(C)CC(C)(C)C[Al](CC(C)(C)CC(C)C)CC(C)(C)CC(C)C NTKCNHURDVTMQK-UHFFFAOYSA-N 0.000 description 1
FHAOCGKAMRAFMM-UHFFFAOYSA-N tris(2-ethylhexyl)alumane Chemical compound CCCCC(CC)C[Al](CC(CC)CCCC)CC(CC)CCCC FHAOCGKAMRAFMM-UHFFFAOYSA-N 0.000 description 1
WCWWRDANFBTPCH-UHFFFAOYSA-N tris(2-methylpentyl)alumane Chemical compound CCCC(C)C[Al](CC(C)CCC)CC(C)CCC WCWWRDANFBTPCH-UHFFFAOYSA-N 0.000 description 1
238000007738 vacuum evaporation Methods 0.000 description 1
238000013022 venting Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

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Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

CA000353683A 1980-02-25 1980-06-10 Polymerisation en solution Expired CA1166400A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US124,373		1980-02-25
US06/124,373 US4302568A (en)	1980-02-25	1980-02-25	Solution polymerization
US30192781A	1981-09-14	1981-09-14
US301,927		1981-09-14

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CA1166400A true CA1166400A (fr)	1984-04-24

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CA000353683A Expired CA1166400A (fr)	1980-02-25	1980-06-10	Polymerisation en solution

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CA (1)	CA1166400A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN117004008A (zh) *	2022-04-29	2023-11-07	辽宁奥克化学股份有限公司	聚氧化乙烯合成催化剂的制备方法和由该方法制备的催化剂及其用途

1980
- 1980-06-10 CA CA000353683A patent/CA1166400A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN117004008A (zh) *	2022-04-29	2023-11-07	辽宁奥克化学股份有限公司	聚氧化乙烯合成催化剂的制备方法和由该方法制备的催化剂及其用途

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Date	Code	Title	Description
2001-04-24	MKEX	Expiry

Publication	Publication Date	Title
US4503204A (en)	1985-03-05	Solution polymerization
US4302568A (en)	1981-11-24	Solution polymerization
US3992561A (en)	1976-11-16	Preparation of solution polymers
EP0318052B1 (fr)	1995-03-15	Polymère séquencé à partir d'un diène et composition de polymère
US4020115A (en)	1977-04-26	Alkaline barium alcoholates
US4033900A (en)	1977-07-05	Composition useful in anionic polymerization
US4297240A (en)	1981-10-27	Solution polymerization
HK1000667B (en)	1998-04-17	Diene block polymer and polymer composition
JPH02265902A (ja)	1990-10-30	高トランス低ビニル共役ジエン系重合体の製造方法
US4307218A (en)	1981-12-22	Solution polymerization
US4048427A (en)	1977-09-13	Preparation of solution polymers
US5580930A (en)	1996-12-03	Rubber composition for tires
US4355156A (en)	1982-10-19	Solution polymerization
US3699190A (en)	1972-10-17	Method for preparing block copolymer
CA1178602A (fr)	1984-11-27	Preparation de polymeres en etoile
EP2307468B1 (fr)	2012-06-13	Pneu et composition élastomère réticulable comprenant un copolymère isotactique obtenu par catalyse homogène
US4260519A (en)	1981-04-07	Preparation of barium-alkoxide salts
US4260712A (en)	1981-04-07	Preparation of barium-alkoxide salts
CA1166400A (fr)	1984-04-24	Polymerisation en solution
US3573249A (en)	1971-03-30	Polymerization of butadiene
US3542906A (en)	1970-11-24	Production of butadiene-styrene graft copolymers with a catalyst containing a nickel complex
US4029718A (en)	1977-06-14	Pivalolactone random graft copolymers
JPH0225365B2 (fr)	1990-06-01
US3591658A (en)	1971-07-06	Production of butadiene-styrene graft copolymers with a nickel carboxylic acid salt-boron trifluoride etherate-trialkylaluminum catalyst
US3639520A (en)	1972-02-01	Production of butadiene-styrene graft copolymers with a nickel carboxylic acid salt or nickel organic complex compound-titanium tetrachloride-trialkylaluminum catalyst

CA1166400A - Polymerisation en solution - Google Patents

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Applications Claiming Priority (4)

Publications (1)

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ID=26822502

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Cited By (1)

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