CA1236824A - Catalyst system and process for polymerizing conjugated dienes - Google Patents
Catalyst system and process for polymerizing conjugated dienesInfo
- Publication number
- CA1236824A CA1236824A CA000476620A CA476620A CA1236824A CA 1236824 A CA1236824 A CA 1236824A CA 000476620 A CA000476620 A CA 000476620A CA 476620 A CA476620 A CA 476620A CA 1236824 A CA1236824 A CA 1236824A
- Authority
- CA
- Canada
- Prior art keywords
- catalyst system
- compound
- lithium
- alkylene
- hydrocarbyl
- 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
- 239000003054 catalyst Substances 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 34
- 150000001993 dienes Chemical class 0.000 title claims abstract description 15
- 230000000379 polymerizing effect Effects 0.000 title claims abstract description 10
- 239000003999 initiator Substances 0.000 claims abstract description 54
- 239000003607 modifier Substances 0.000 claims abstract description 48
- -1 cyclic acetal Chemical class 0.000 claims abstract description 42
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 35
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims abstract description 34
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229920000642 polymer Polymers 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 229940015043 glyoxal Drugs 0.000 claims abstract description 17
- 125000000129 anionic group Chemical group 0.000 claims abstract description 13
- 125000005702 oxyalkylene group Chemical group 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract 11
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 150000002901 organomagnesium compounds Chemical class 0.000 claims abstract 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 44
- 238000006116 polymerization reaction Methods 0.000 claims description 36
- 239000000178 monomer Substances 0.000 claims description 18
- 229910052749 magnesium Inorganic materials 0.000 claims description 14
- 239000011777 magnesium Substances 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 12
- 229910052782 aluminium Inorganic materials 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 11
- 150000002681 magnesium compounds Chemical class 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- 150000001491 aromatic compounds Chemical class 0.000 claims description 5
- 150000002642 lithium compounds Chemical class 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 235000001055 magnesium Nutrition 0.000 claims 2
- 229940091250 magnesium supplement Drugs 0.000 claims 2
- 239000012454 non-polar solvent Substances 0.000 claims 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- 150000001721 carbon Chemical group 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 241000125205 Anethum Species 0.000 description 8
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 8
- 229920000180 alkyd Polymers 0.000 description 8
- 229920001971 elastomer Polymers 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KJJBSBKRXUVBMX-UHFFFAOYSA-N magnesium;butane Chemical compound [Mg+2].CCC[CH2-].CCC[CH2-] KJJBSBKRXUVBMX-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000005062 Polybutadiene Substances 0.000 description 5
- 150000002902 organometallic compounds Chemical class 0.000 description 5
- 125000002524 organometallic group Chemical group 0.000 description 5
- 229920002857 polybutadiene Polymers 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 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
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000282320 Panthera leo Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000005060 rubber Substances 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
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical group CC(C)=C(C)C WGLLSSPDPJPLOR-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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
- 240000005595 Echinocereus dasyacanthus Species 0.000 description 2
- 235000008314 Echinocereus dasyacanthus Nutrition 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 2
- 208000037062 Polyps Diseases 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002900 organolithium compounds Chemical class 0.000 description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- BOGRNZQRTNVZCZ-AATRIKPKSA-N (3e)-3-methylpenta-1,3-diene Chemical compound C\C=C(/C)C=C BOGRNZQRTNVZCZ-AATRIKPKSA-N 0.000 description 1
- OGQVROWWFUXRST-FNORWQNLSA-N (3e)-hepta-1,3-diene Chemical compound CCC\C=C\C=C OGQVROWWFUXRST-FNORWQNLSA-N 0.000 description 1
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- BOGRNZQRTNVZCZ-UHFFFAOYSA-N 1,2-dimethyl-butadiene Natural products CC=C(C)C=C BOGRNZQRTNVZCZ-UHFFFAOYSA-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
- HVOKBODBWQEEGI-UHFFFAOYSA-N 1-ethenyl-3,5-diethylbenzene Chemical compound CCC1=CC(CC)=CC(C=C)=C1 HVOKBODBWQEEGI-UHFFFAOYSA-N 0.000 description 1
- QDLUTRRUISEVDW-UHFFFAOYSA-N 1-ethenyl-3,5-diphenoxybenzene Chemical compound C=1C(OC=2C=CC=CC=2)=CC(C=C)=CC=1OC1=CC=CC=C1 QDLUTRRUISEVDW-UHFFFAOYSA-N 0.000 description 1
- ITZRCVCLPNYQNR-UHFFFAOYSA-N 1-ethenyl-3,6-bis(4-methylphenyl)naphthalene Chemical compound C1=CC(C)=CC=C1C1=CC=C(C(C=C)=CC(=C2)C=3C=CC(C)=CC=3)C2=C1 ITZRCVCLPNYQNR-UHFFFAOYSA-N 0.000 description 1
- SQOPXLQDBNQBOP-UHFFFAOYSA-N 1-ethenyl-3,6-dihexylnaphthalene Chemical compound C=CC1=CC(CCCCCC)=CC2=CC(CCCCCC)=CC=C21 SQOPXLQDBNQBOP-UHFFFAOYSA-N 0.000 description 1
- LFZRKMOWVSTEMD-UHFFFAOYSA-N 1-ethenyl-3-ethylnaphthalene Chemical compound C1=CC=CC2=CC(CC)=CC(C=C)=C21 LFZRKMOWVSTEMD-UHFFFAOYSA-N 0.000 description 1
- XTUJFEHBYGQMFD-UHFFFAOYSA-N 1-ethenyl-3-hexyl-5-methylbenzene Chemical compound CCCCCCC1=CC(C)=CC(C=C)=C1 XTUJFEHBYGQMFD-UHFFFAOYSA-N 0.000 description 1
- FWNGRKSQEBCGAX-UHFFFAOYSA-N 1-ethenyl-4,5-dimethylnaphthalene Chemical compound C1=CC(C)=C2C(C)=CC=CC2=C1C=C FWNGRKSQEBCGAX-UHFFFAOYSA-N 0.000 description 1
- UDBOTPBQDGDMHZ-UHFFFAOYSA-N 1-ethenyl-4-methoxynaphthalene Chemical compound C1=CC=C2C(OC)=CC=C(C=C)C2=C1 UDBOTPBQDGDMHZ-UHFFFAOYSA-N 0.000 description 1
- UVRJZDWOXMDOLE-UHFFFAOYSA-N 1-ethenyl-5-(2,4,6-trimethylphenyl)naphthalene Chemical compound CC1=CC(C)=CC(C)=C1C1=CC=CC2=C(C=C)C=CC=C12 UVRJZDWOXMDOLE-UHFFFAOYSA-N 0.000 description 1
- KXHFPILRDXTWCG-UHFFFAOYSA-N 1-ethenyl-6-phenoxynaphthalene Chemical compound C=1C=C2C(C=C)=CC=CC2=CC=1OC1=CC=CC=C1 KXHFPILRDXTWCG-UHFFFAOYSA-N 0.000 description 1
- HGJHLJMJLXNPCN-UHFFFAOYSA-N 1-ethenyl-8-phenylnaphthalene Chemical compound C=12C(C=C)=CC=CC2=CC=CC=1C1=CC=CC=C1 HGJHLJMJLXNPCN-UHFFFAOYSA-N 0.000 description 1
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
- ABERXULXRGIGTD-UHFFFAOYSA-N 2-dodecyl-7-ethenylnaphthalene Chemical compound C1=CC(C=C)=CC2=CC(CCCCCCCCCCCC)=CC=C21 ABERXULXRGIGTD-UHFFFAOYSA-N 0.000 description 1
- PDELBHCVXBSVPJ-UHFFFAOYSA-N 2-ethenyl-1,3,5-trimethylbenzene Chemical class CC1=CC(C)=C(C=C)C(C)=C1 PDELBHCVXBSVPJ-UHFFFAOYSA-N 0.000 description 1
- QKZQFURPHHQMCN-UHFFFAOYSA-N 2-ethoxy-3-methylhexa-1,3-diene Chemical compound CCOC(=C)C(C)=CCC QKZQFURPHHQMCN-UHFFFAOYSA-N 0.000 description 1
- UNBLCMHLEQHORH-UHFFFAOYSA-N 2-ethoxy-3-methylidenepent-1-ene Chemical compound CCOC(=C)C(=C)CC UNBLCMHLEQHORH-UHFFFAOYSA-N 0.000 description 1
- LYGKSUOGJYYSOI-UHFFFAOYSA-N 2-methoxybuta-1,3-diene Chemical compound COC(=C)C=C LYGKSUOGJYYSOI-UHFFFAOYSA-N 0.000 description 1
- PJXJBPMWCKMWLS-UHFFFAOYSA-N 2-methyl-3-methylidenepent-1-ene Chemical compound CCC(=C)C(C)=C PJXJBPMWCKMWLS-UHFFFAOYSA-N 0.000 description 1
- KUFLEYZWYCAZCC-UHFFFAOYSA-N 2-methylhexa-1,3-diene Chemical compound CCC=CC(C)=C KUFLEYZWYCAZCC-UHFFFAOYSA-N 0.000 description 1
- QTTAWIGVQMSWMV-UHFFFAOYSA-N 3,4-dimethylhexa-1,3-diene Chemical compound CCC(C)=C(C)C=C QTTAWIGVQMSWMV-UHFFFAOYSA-N 0.000 description 1
- NKNFAANDGREMJT-UHFFFAOYSA-N 3-ethenyl-1-(4-methylphenyl)naphthalene Chemical compound C1=CC(C)=CC=C1C1=CC(C=C)=CC2=CC=CC=C12 NKNFAANDGREMJT-UHFFFAOYSA-N 0.000 description 1
- QXNYNMNRJMHGHH-UHFFFAOYSA-N 3-ethyl-2-methylpenta-1,3-diene Chemical compound CCC(=CC)C(C)=C QXNYNMNRJMHGHH-UHFFFAOYSA-N 0.000 description 1
- CTNXNQQXFSVMIY-UHFFFAOYSA-N 3-ethylidenehex-1-ene Chemical compound CCCC(=CC)C=C CTNXNQQXFSVMIY-UHFFFAOYSA-N 0.000 description 1
- GITIYCQMJWQMKC-UHFFFAOYSA-N 3-methylhepta-1,3-diene Chemical compound CCCC=C(C)C=C GITIYCQMJWQMKC-UHFFFAOYSA-N 0.000 description 1
- SALPZWUZFRNPQX-UHFFFAOYSA-N 4,5-dimethylideneoctane Chemical compound CCCC(=C)C(=C)CCC SALPZWUZFRNPQX-UHFFFAOYSA-N 0.000 description 1
- NZGZIYSKIDVYSM-UHFFFAOYSA-N 4-ethenyl-1,2,7,8-tetramethylnaphthalene Chemical compound C=CC1=CC(C)=C(C)C2=C(C)C(C)=CC=C21 NZGZIYSKIDVYSM-UHFFFAOYSA-N 0.000 description 1
- GQWAOUOHRMHSHL-UHFFFAOYSA-N 4-ethenyl-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(C=C)C=C1 GQWAOUOHRMHSHL-UHFFFAOYSA-N 0.000 description 1
- ZSNRMRKAYAJYRZ-UHFFFAOYSA-N 4-methylidenehex-2-ene Chemical compound CCC(=C)C=CC ZSNRMRKAYAJYRZ-UHFFFAOYSA-N 0.000 description 1
- ISOZCELAVOWCBX-UHFFFAOYSA-N 5-ethenyl-1-n,3-n-diethylbenzene-1,3-diamine Chemical compound CCNC1=CC(NCC)=CC(C=C)=C1 ISOZCELAVOWCBX-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
- GYLGGODPGFTNRX-UHFFFAOYSA-N 6-cyclohexyl-1-ethenylnaphthalene Chemical compound C=1C=C2C(C=C)=CC=CC2=CC=1C1CCCCC1 GYLGGODPGFTNRX-UHFFFAOYSA-N 0.000 description 1
- CVLVQJAXBADOOC-UHFFFAOYSA-N 6-ethenyl-1,2-diethyl-7-methyl-4-propylnaphthalene Chemical compound CC1=C(C=C)C=C2C(CCC)=CC(CC)=C(CC)C2=C1 CVLVQJAXBADOOC-UHFFFAOYSA-N 0.000 description 1
- RRGRCBYNXFIHGR-UHFFFAOYSA-N 8-butyl-3-ethenyl-1-propylnaphthalene Chemical compound C=CC1=CC(CCC)=C2C(CCCC)=CC=CC2=C1 RRGRCBYNXFIHGR-UHFFFAOYSA-N 0.000 description 1
- 108700028369 Alleles Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- DBNGNEQZXBWPTJ-UHFFFAOYSA-N CCCC[Mg]C(C)CC Chemical compound CCCC[Mg]C(C)CC DBNGNEQZXBWPTJ-UHFFFAOYSA-N 0.000 description 1
- 241001315286 Damon Species 0.000 description 1
- 241001644893 Entandrophragma utile Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 1
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- LEKSIJZGSFETSJ-UHFFFAOYSA-N cyclohexane;lithium Chemical compound [Li]C1CCCCC1 LEKSIJZGSFETSJ-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 125000002734 organomagnesium group Chemical group 0.000 description 1
- FCBQCNJKXDUDPV-UHFFFAOYSA-N oxaldehyde;phenol Chemical compound O=CC=O.OC1=CC=CC=C1 FCBQCNJKXDUDPV-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000004351 phenylcyclohexyl group Chemical group C1(=CC=CC=C1)C1(CCCCC1)* 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
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004079 stearyl 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])C([H])([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
- 239000010959 steel Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US627,246 | 1984-07-02 | ||
| US06/627,246 US4520123A (en) | 1984-07-02 | 1984-07-02 | Catalyst system and process for polymerizing conjugated dienes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1236824A true CA1236824A (en) | 1988-05-17 |
Family
ID=24513849
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000476620A Expired CA1236824A (en) | 1984-07-02 | 1985-03-15 | Catalyst system and process for polymerizing conjugated dienes |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4520123A (en, 2012) |
| EP (1) | EP0171497B1 (en, 2012) |
| JP (1) | JPS6119610A (en, 2012) |
| CA (1) | CA1236824A (en, 2012) |
| DE (1) | DE3567882D1 (en, 2012) |
| ES (1) | ES8604269A1 (en, 2012) |
| ZA (1) | ZA851662B (en, 2012) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4696986A (en) * | 1986-08-12 | 1987-09-29 | The Goodyear Tire & Rubber Company | Modifier for lithium catalysts |
| US5112929A (en) * | 1991-04-05 | 1992-05-12 | Bridgestone Corporation | Oxolanyl cyclic acetals as anionic polymerization modifiers |
| GB9112419D0 (en) * | 1991-06-10 | 1991-07-31 | Shell Int Research | Process for polymer preparation |
| IT1265048B1 (it) * | 1993-08-06 | 1996-10-28 | Eniricerche Spa | Complessi metallorganici dei lantanidi e loro uso nella polimerizzazione di monomeri insaturi |
| US5610227A (en) * | 1995-06-07 | 1997-03-11 | Bridgestone/Firestone, Inc. | Lithium amino magnesiate polymerization initiators and elastomers having reduced hysteresis |
| US5700888A (en) * | 1996-11-07 | 1997-12-23 | Bridgestone Corporation | Synthesis of macrocyclic polymers having low hysteresis compounded properties |
| US5728782A (en) * | 1996-12-06 | 1998-03-17 | Union Carbide Chemicals & Plastics Technology Corporation | Gas phase anionic polymerization of dienes and vinyl-substituted aromatic compounds |
| US6071847A (en) | 1998-03-13 | 2000-06-06 | Bridgestone Corporation | Gas phase anionic polymerization of diene elastomers |
| US6136914A (en) | 1998-03-13 | 2000-10-24 | Bridgestone Corporation | Anionic polymerization initiators for preparing macro-branched diene rubbers |
| US6140444A (en) * | 1999-01-19 | 2000-10-31 | Loctite Corporation | Catalyst system, process, and silicone compositions |
| US6391981B1 (en) | 1999-04-23 | 2002-05-21 | Kraton Polymers Us Llc | Increased throughput in the manufacture of anionic polymers by reduction in polymer cement viscosity through the addition of metal alkyls |
| US6455651B1 (en) | 1999-04-23 | 2002-09-24 | Kraton Polymers U.S. Llc | Uniform initiation of anionic polymerization using organo-substituted alkali metal initiators |
| US6906147B2 (en) * | 2002-03-20 | 2005-06-14 | Cyclics Corporation | Catalytic systems |
| US7256241B2 (en) * | 2000-01-21 | 2007-08-14 | Cyclics Corporation | Methods for polymerizing macrocyclic polyester oligomers using catalyst promoters |
| US20020198343A1 (en) * | 2000-03-14 | 2002-12-26 | Willis Carl Lesley | Uniform initiation of anionic polymerization using organo-substituted alkali metal initiators |
| US7767781B2 (en) * | 2000-09-01 | 2010-08-03 | Cyclics Corporation | Preparation of low-acid polyalkylene terephthalate and preparation of macrocyclic polyester oligomer therefrom |
| US7750109B2 (en) | 2000-09-01 | 2010-07-06 | Cyclics Corporation | Use of a residual oligomer recyclate in the production of macrocyclic polyester oligomer |
| KR100779769B1 (ko) * | 2000-09-01 | 2007-11-27 | 시클릭스 코포레이션 | 선형 폴리에스테르를 거대고리 올리고에스테르 조성물로전환시키는 방법 및 거대고리 올리고에스테르 |
| US7304123B2 (en) * | 2001-06-27 | 2007-12-04 | Cyclics Corporation | Processes for shaping macrocyclic oligoesters |
| JP2005515965A (ja) * | 2001-06-27 | 2005-06-02 | サイクリクス コーポレイション | 大環状オリゴエステルの単離、処方、および成形 |
| US6787632B2 (en) * | 2001-10-09 | 2004-09-07 | Cyclics Corporation | Organo-titanate catalysts for preparing pure macrocyclic oligoesters |
| AU2003249169A1 (en) * | 2002-07-11 | 2004-02-02 | Harvey Emerson Atwood | Coupled styrenic block copolymers and process for preparing same |
| SG159473A1 (en) * | 2008-08-27 | 2010-03-30 | Sumitomo Chemical Co | Conjugated diene polymer, conjugated diene polymer composition, and method for producing conjugated diene polymer |
| KR101762461B1 (ko) | 2009-10-14 | 2017-07-27 | 가부시키가이샤 브리지스톤 | 환식 비환식 디엔 공중합체의 제조 방법 및 고무 조성물 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3157604A (en) * | 1960-10-24 | 1964-11-17 | Phillips Petroleum Co | Polymerization initiators |
| US3091606A (en) * | 1960-11-21 | 1963-05-28 | Phillips Petroleum Co | Organolithium polymerization initiator prepared in the presence of a small amount of sodium |
| US3207742A (en) * | 1962-03-26 | 1965-09-21 | Exxon Research Engineering Co | Polymerization of 1, 3-dienes in the presence of hexamethylphosphoramide |
| US3301824A (en) * | 1963-09-26 | 1967-01-31 | Union Carbide Corp | Polymers of cyclic carbonates |
| US3451988A (en) * | 1966-10-25 | 1969-06-24 | Exxon Research Engineering Co | Polymerization catalyst and uses thereof |
| US3585168A (en) * | 1968-09-21 | 1971-06-15 | Shohei Inoue | Process for producing copolymer of epoxide and carbon dioxide |
| US3646321A (en) * | 1970-06-22 | 1972-02-29 | Gen Motors Corp | Infrared surface heating unit |
| US3847883A (en) * | 1970-07-23 | 1974-11-12 | Gulf Research Development Co | Method of preparing polymers utilizing as catalysts hydrocarbon-soluble complexes of an organomagnesium compound with a group i organometallic compound |
| US3822219A (en) * | 1970-07-23 | 1974-07-02 | Gulf Resources & Chem Corp | Catalyst composition |
| US3817955A (en) * | 1970-08-24 | 1974-06-18 | Gulf Resources & Chem Corp | Preparation of polymers using complexes of organomagnesiums with certain hydrides as catalysts |
| US3846385A (en) * | 1973-07-16 | 1974-11-05 | Gen Tire & Rubber Co | Preparation of solution polymers using a barium di-tert alkoxide and a di-butyl magnesium catalyst complex |
| US4139490A (en) * | 1977-11-07 | 1979-02-13 | The Firestone Tire & Rubber Company | Dehydrocarbyl magnesium and an alkali metal compound catalyst composition for polymerizing conjugated dienes |
| US4264753A (en) * | 1979-10-18 | 1981-04-28 | The Firestone Tire & Rubber Company | Process for polymerizing conjugated dienes |
| US4429090A (en) * | 1983-03-09 | 1984-01-31 | The Firestone Tire & Rubber Company | Catalyst containing oligomeric oxolanyl alkane modifiers and process for the production of polymers having increased 1,2-microstructure |
| US4429091A (en) * | 1983-03-09 | 1984-01-31 | The Firestone Tire & Rubber Company | Oligomeric oxolanyl alkanes as modifiers for polymerization of dienes using lithium-based initiators |
-
1984
- 1984-07-02 US US06/627,246 patent/US4520123A/en not_active Expired - Lifetime
-
1985
- 1985-03-05 ZA ZA851662A patent/ZA851662B/xx unknown
- 1985-03-13 DE DE8585102889T patent/DE3567882D1/de not_active Expired
- 1985-03-13 EP EP85102889A patent/EP0171497B1/en not_active Expired
- 1985-03-15 CA CA000476620A patent/CA1236824A/en not_active Expired
- 1985-05-10 JP JP60098175A patent/JPS6119610A/ja active Granted
- 1985-07-01 ES ES544742A patent/ES8604269A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0171497B1 (en) | 1989-01-25 |
| US4520123A (en) | 1985-05-28 |
| ES544742A0 (es) | 1986-01-16 |
| DE3567882D1 (en) | 1989-03-02 |
| JPS6119610A (ja) | 1986-01-28 |
| JPH0215563B2 (en, 2012) | 1990-04-12 |
| ZA851662B (en) | 1985-10-30 |
| EP0171497A1 (en) | 1986-02-19 |
| ES8604269A1 (es) | 1986-01-16 |
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