CA1236648A - Controlling the molecular weight of polybutadiene - Google Patents
Controlling the molecular weight of polybutadieneInfo
- Publication number
- CA1236648A CA1236648A CA000425670A CA425670A CA1236648A CA 1236648 A CA1236648 A CA 1236648A CA 000425670 A CA000425670 A CA 000425670A CA 425670 A CA425670 A CA 425670A CA 1236648 A CA1236648 A CA 1236648A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- hydrogen fluoride
- nickel
- butadiene
- molecular weight
- 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
- 239000005062 Polybutadiene Substances 0.000 title abstract description 16
- 229920002857 polybutadiene Polymers 0.000 title abstract description 16
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 77
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 50
- 239000003054 catalyst Substances 0.000 claims abstract description 47
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 46
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 23
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 14
- 239000011737 fluorine Substances 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 12
- 150000001336 alkenes Chemical class 0.000 claims abstract description 10
- 150000002148 esters Chemical class 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 7
- 229920003193 cis-1,4-polybutadiene polymer Polymers 0.000 claims abstract description 7
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 6
- 239000011707 mineral Substances 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 4
- 239000003849 aromatic solvent Substances 0.000 claims abstract description 3
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims abstract 6
- 150000001361 allenes Chemical class 0.000 claims abstract 2
- 230000000536 complexating effect Effects 0.000 claims abstract 2
- 150000002576 ketones Chemical class 0.000 claims abstract 2
- 150000002825 nitriles Chemical class 0.000 claims abstract 2
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims abstract 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 12
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 claims description 7
- 150000002815 nickel Chemical class 0.000 claims description 6
- 150000002816 nickel compounds Chemical class 0.000 claims description 6
- DVTHIMLUHWEZOM-UHFFFAOYSA-L nickel(2+);octanoate Chemical compound [Ni+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O DVTHIMLUHWEZOM-UHFFFAOYSA-L 0.000 claims description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 5
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 150000002222 fluorine compounds Chemical class 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 39
- 229910052759 nickel Inorganic materials 0.000 description 21
- 229920000642 polymer Polymers 0.000 description 21
- -1 aluminum halide compounds Chemical class 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 12
- 229920000180 alkyd Polymers 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- 150000004678 hydrides Chemical class 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 108700028369 Alleles Proteins 0.000 description 5
- 229910015900 BF3 Inorganic materials 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 235000010210 aluminium Nutrition 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 150000002826 nitrites Chemical class 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
- 241000282320 Panthera leo Species 0.000 description 3
- 208000037062 Polyps Diseases 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 235000013847 iso-butane Nutrition 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 241001125840 Coryphaenidae Species 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 241001441571 Hiodontidae Species 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 244000228367 Lewisia rediviva Species 0.000 description 2
- 235000007279 Lewisia rediviva Nutrition 0.000 description 2
- 241000570861 Mandragora autumnalis Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 2
- YYZUSRORWSJGET-UHFFFAOYSA-N ethyl octanoate Chemical compound CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 2
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 2
- 239000003517 fume Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- IPBVNPXQWQGGJP-UHFFFAOYSA-N phenyl acetate Chemical compound CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- SVJIEGOVQBGOSU-UHFFFAOYSA-N (4-methylphenyl)-propan-2-ylalumane Chemical class C1(=CC=C(C=C1)[AlH]C(C)C)C SVJIEGOVQBGOSU-UHFFFAOYSA-N 0.000 description 1
- PRPLGWFQYUPYBN-UHFFFAOYSA-N (4-methylphenyl)-propylalumane Chemical class C1(=CC=C(C=C1)[AlH]CCC)C PRPLGWFQYUPYBN-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
- JRCZSHDOYYZKAW-UHFFFAOYSA-N 2-(4-methylphenyl)ethylalumane Chemical class C1(=CC=C(C=C1)CC[AlH2])C JRCZSHDOYYZKAW-UHFFFAOYSA-N 0.000 description 1
- UENGQMOTDCLRTI-UHFFFAOYSA-N 2-butylcycloheptan-1-one Chemical compound CCCCC1CCCCCC1=O UENGQMOTDCLRTI-UHFFFAOYSA-N 0.000 description 1
- XRBQEYWBWZFUIJ-UHFFFAOYSA-N 2-ethylhexanoic acid;nickel Chemical compound [Ni].CCCCC(CC)C(O)=O XRBQEYWBWZFUIJ-UHFFFAOYSA-N 0.000 description 1
- KMLLIQHJMAYJKV-UHFFFAOYSA-N 2-methylbenzaldehyde;hydrofluoride Chemical compound F.CC1=CC=CC=C1C=O KMLLIQHJMAYJKV-UHFFFAOYSA-N 0.000 description 1
- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 description 1
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241001315286 Damon Species 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- OTUKPXUUYJTFFJ-UHFFFAOYSA-N F.CC(C)=O Chemical compound F.CC(C)=O OTUKPXUUYJTFFJ-UHFFFAOYSA-N 0.000 description 1
- 241000976924 Inca Species 0.000 description 1
- JSHDAORXSNJOBA-UHFFFAOYSA-N Isopropyl hexanoate Chemical compound CCCCCC(=O)OC(C)C JSHDAORXSNJOBA-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241001417495 Serranidae Species 0.000 description 1
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000005441 aurora Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- AIWXNWDZGADCFW-UHFFFAOYSA-N benzyl(propan-2-yl)alumane Chemical class C(C1=CC=CC=C1)[AlH]C(C)C AIWXNWDZGADCFW-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical class CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
- LLHTVHHWJJDSSP-UHFFFAOYSA-N bis(4-methylphenyl)alumane Chemical class C1(=CC=C(C=C1)[AlH]C1=CC=C(C=C1)C)C LLHTVHHWJJDSSP-UHFFFAOYSA-N 0.000 description 1
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 230000002153 concerted effect Effects 0.000 description 1
- TWKFYCJMKMVFCV-UHFFFAOYSA-N cyclopenta-1,3-diene;nickel Chemical compound [Ni].C=1C=C[CH-]C=1 TWKFYCJMKMVFCV-UHFFFAOYSA-N 0.000 description 1
- KZPXREABEBSAQM-UHFFFAOYSA-N cyclopenta-1,3-diene;nickel(2+) Chemical compound [Ni+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KZPXREABEBSAQM-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- OTACYDLCOLOKPA-UHFFFAOYSA-N dibenzyl(ethyl)alumane Chemical compound C=1C=CC=CC=1C[Al](CC)CC1=CC=CC=C1 OTACYDLCOLOKPA-UHFFFAOYSA-N 0.000 description 1
- DODCHQVKECHKRP-UHFFFAOYSA-N dibenzylalumane Chemical class C(C1=CC=CC=C1)[AlH]CC1=CC=CC=C1 DODCHQVKECHKRP-UHFFFAOYSA-N 0.000 description 1
- PASXEHKLXCTXJM-UHFFFAOYSA-N diethyl-(4-methylphenyl)alumane Chemical compound CC[Al](CC)C1=CC=C(C)C=C1 PASXEHKLXCTXJM-UHFFFAOYSA-N 0.000 description 1
- HIVRDDZUKVNKAO-UHFFFAOYSA-N diphenylalumane Chemical class C1(=CC=CC=C1)[AlH]C1=CC=CC=C1 HIVRDDZUKVNKAO-UHFFFAOYSA-N 0.000 description 1
- OWWVAVMUYQFBOC-UHFFFAOYSA-N diphenylmethanone;hydrofluoride Chemical compound [H+].[F-].C=1C=CC=CC=1C(=O)C1=CC=CC=C1 OWWVAVMUYQFBOC-UHFFFAOYSA-N 0.000 description 1
- XOCWTYIVWYOSGQ-UHFFFAOYSA-N dipropylalumane Chemical class C(CC)[AlH]CCC XOCWTYIVWYOSGQ-UHFFFAOYSA-N 0.000 description 1
- 239000010436 fluorite Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Substances CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- BGEHHAVMRVXCGR-UHFFFAOYSA-N methylundecylketone Natural products CCCCCCCCCCCCC=O BGEHHAVMRVXCGR-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- UIEKYBOPAVTZKW-UHFFFAOYSA-L naphthalene-2-carboxylate;nickel(2+) Chemical compound [Ni+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 UIEKYBOPAVTZKW-UHFFFAOYSA-L 0.000 description 1
- 229940078494 nickel acetate Drugs 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
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- YPGFUNWVIKECSK-UHFFFAOYSA-N phenyl acetate;hydrofluoride Chemical compound F.CC(=O)OC1=CC=CC=C1 YPGFUNWVIKECSK-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- ZKGDHJAHOGRQEP-UHFFFAOYSA-N phenyl(propyl)alumane Chemical class C1(=CC=CC=C1)[AlH]CCC ZKGDHJAHOGRQEP-UHFFFAOYSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000015106 stout Nutrition 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- MCWWHQMTJNSXPX-UHFFFAOYSA-N tribenzylalumane Chemical compound C=1C=CC=CC=1C[Al](CC=1C=CC=CC=1)CC1=CC=CC=C1 MCWWHQMTJNSXPX-UHFFFAOYSA-N 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
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 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
- JQPMDTQDAXRDGS-UHFFFAOYSA-N triphenylalumane Chemical compound C1=CC=CC=C1[Al](C=1C=CC=CC=1)C1=CC=CC=C1 JQPMDTQDAXRDGS-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 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
- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers 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
- C08F136/04—Homopolymers 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
- C08F136/06—Butadiene
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/903—Monomer polymerized in presence of transition metal containing catalyst and hydrocarbon additive affecting polymer properties of catalyst activity
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)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37184182A | 1982-04-26 | 1982-04-26 | |
| US371,841 | 1995-01-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1236648A true CA1236648A (en) | 1988-05-10 |
Family
ID=23465614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000425670A Expired CA1236648A (en) | 1982-04-26 | 1983-04-12 | Controlling the molecular weight of polybutadiene |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5698643A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0093074B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS58196214A (cg-RX-API-DMAC7.html) |
| AU (1) | AU558437B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR8301899A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1236648A (cg-RX-API-DMAC7.html) |
| DE (1) | DE3372971D1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES521805A0 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA832555B (cg-RX-API-DMAC7.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1637549A1 (en) | 2004-08-30 | 2006-03-22 | The Goodyear Tire & Rubber Company | Synthesis of CIS-1,4-polybutadiene |
Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN173082B (cg-RX-API-DMAC7.html) * | 1986-02-19 | 1994-02-05 | Goodyear Tire & Rubber | |
| RU2109760C1 (ru) * | 1996-09-23 | 1998-04-27 | Акционерное общество открытого типа "Ефремовский завод синтетического каучука" | Способ получения сополимера бутадиена с изобутиленом |
| USH2036H1 (en) | 1999-06-02 | 2002-07-02 | The Goodyear Tire & Rubber Company | High cis-1,4-polybutadiene rubber compounds |
| US6479601B1 (en) | 1999-08-06 | 2002-11-12 | The Goodyear Tire & Rubber Company | Transition metal catalysts for diene polymerizations |
| US6939920B2 (en) * | 2001-01-08 | 2005-09-06 | The Goodyear Tire & Rubber Company | Tire sidewall compounds having improved flex fatigue and tread compound having improved tear strength |
| US8372925B2 (en) * | 2007-04-10 | 2013-02-12 | Bridgestone Corporation | Nickel-based catalyst composition |
| EP2658886B1 (en) | 2010-12-31 | 2017-03-08 | Bridgestone Corporation | Bulk polymerization of conjugated dienes using a nickel-based catalyst system |
| KR101860969B1 (ko) | 2010-12-31 | 2018-05-24 | 가부시키가이샤 브리지스톤 | 니켈-기재 촉매시스템을 이용한 공액 디엔의 벌크중합 |
| KR101896136B1 (ko) | 2011-05-09 | 2018-09-07 | 가부시키가이샤 브리지스톤 | 고-cis 폴리디엔 제조방법 |
| EP3622843B1 (en) | 2018-09-13 | 2023-01-25 | The Goodyear Tire & Rubber Company | Resin modified oil extended rubber |
| US11220595B2 (en) | 2019-03-04 | 2022-01-11 | The Goodyear Tire & Rubber Company | Reinforced rubber containing silylated triglyceride oil |
| US11560462B1 (en) | 2019-09-20 | 2023-01-24 | The Goodyear Tire & Rubber Company | Functionalized high cis-1,4-polybutadiene |
| US11851549B2 (en) | 2019-11-11 | 2023-12-26 | The Goodyear Tire & Rubber Company | Tire |
| EP3831873B1 (en) | 2019-12-03 | 2025-04-23 | The Goodyear Tire & Rubber Company | Rubber composition and an article of manufacture comprising a rubber composition |
| EP3835350A3 (en) | 2019-12-12 | 2021-07-14 | The Goodyear Tire & Rubber Company | A rubber composition and a tire |
| EP3838617B1 (en) | 2019-12-20 | 2022-12-21 | The Goodyear Tire & Rubber Company | Tire |
| EP3888940B1 (en) | 2020-04-01 | 2023-01-11 | The Goodyear Tire & Rubber Company | A rubber composition and a rubber product |
| EP3896125B1 (en) | 2020-04-16 | 2024-10-02 | The Goodyear Tire & Rubber Company | A rubber composition and a rubber product |
| US20210395501A1 (en) | 2020-06-19 | 2021-12-23 | The Goodyear Tire & Rubber Company | Rubber composition and a tire |
| US12006436B2 (en) | 2020-11-13 | 2024-06-11 | The Goodyear Tire & Rubber Company | Rubber composition and a tire |
| EP4015237B1 (en) | 2020-12-17 | 2026-01-28 | The Goodyear Tire & Rubber Company | Rubber composition offering high stiffness and low hysteresis, method of manufacturing and tire |
| EP4056640B1 (en) | 2021-03-09 | 2026-04-29 | The Goodyear Tire & Rubber Company | A rubber composition and a tire |
| EP4056644B1 (en) | 2021-03-09 | 2026-04-29 | The Goodyear Tire & Rubber Company | A rubber composition and a tire |
| EP4056643A1 (en) | 2021-03-09 | 2022-09-14 | The Goodyear Tire & Rubber Company | A rubber composition and a tire |
| US12304979B2 (en) | 2021-04-27 | 2025-05-20 | The Goodyear Tire & Rubber Company | Diene-based elastomer and a rubber composition |
| US12037437B2 (en) | 2021-05-28 | 2024-07-16 | The Goodyear Tire & Rubber Company | Rubber composition comprising a block-copolymer |
| US12187895B2 (en) | 2021-08-26 | 2025-01-07 | The Goodyear Tire & Rubber Company | Rubber composition and a tire |
| US20230101160A1 (en) | 2021-09-30 | 2023-03-30 | The Goodyear Tire & Rubber Company | Rubber composition and tire |
| US20230094443A1 (en) | 2021-09-30 | 2023-03-30 | The Goodyear Tire & Rubber Company | Rubber composition and tire |
| US12679141B2 (en) | 2021-09-30 | 2026-07-14 | The Goodyear Tire & Rubber Company | Rubber composition and tire |
| US20230124971A1 (en) | 2021-10-11 | 2023-04-20 | The Goodyear Tire & Rubber Company | Rubber composition and a tire |
| EP4183595B1 (en) | 2021-11-19 | 2025-02-19 | The Goodyear Tire & Rubber Company | A tire having an improved shoulder design |
| EP4190589A1 (en) | 2021-12-02 | 2023-06-07 | The Goodyear Tire & Rubber Company | Tire tread rubber composition comprising rice husk ash silica |
| US12698380B2 (en) | 2022-03-28 | 2026-08-04 | The Goodyear Tire & Rubber Company | Rubber composition for a winter tire and a winter tire |
| US20230323075A1 (en) | 2022-04-12 | 2023-10-12 | The Goodyear Tire & Rubber Company | Rubber composition and a tire |
| US20230323103A1 (en) | 2022-04-12 | 2023-10-12 | The Goodyear Tire & Rubber Company | Rubber composition and a tire |
| US11987705B2 (en) | 2022-05-26 | 2024-05-21 | The Goodyear Tire & Rubber Company | Rubber composition and a tire comprising a rubber composition |
| US20240042799A1 (en) | 2022-07-28 | 2024-02-08 | The Goodyear Tire & Rubber Company | Rubber composition and truck tire |
| US12503532B2 (en) | 2022-07-28 | 2025-12-23 | The Goodyear Tire & Rubber Company | Rubber composition and truck tire |
| US12264209B2 (en) | 2022-07-28 | 2025-04-01 | The Goodyear Tire & Rubber Company | Rubber composition and truck tire |
| US12263705B2 (en) | 2022-09-09 | 2025-04-01 | The Goodyear Tire & Rubber Company | Tire |
| US12583952B2 (en) | 2022-12-14 | 2026-03-24 | The Goodyear Tire & Rubber Company | Rubber composition and tire |
| US20240209188A1 (en) | 2022-12-14 | 2024-06-27 | The Goodyear Tire & Rubber Company | Synthetic polyisoprene and method of synthesizing polyisoprene |
| US20240326514A1 (en) | 2023-03-30 | 2024-10-03 | The Goodyear Tire & Rubber Company | Tire comprising a tread |
| US20240360299A1 (en) | 2023-04-25 | 2024-10-31 | The Goodyear Tire & Rubber Company | Pneumatic tire tread |
| US20240376241A1 (en) | 2023-05-10 | 2024-11-14 | The Goodyear Tire & Rubber Company | Diene-norbornene copolymers |
| US20250001812A1 (en) | 2023-06-29 | 2025-01-02 | The Goodyear Tire & Rubber Company | Tire having a sidewall with multiple layers |
| US20250019526A1 (en) | 2023-07-10 | 2025-01-16 | The Goodyear Tire & Rubber Company | Winter tread composition including aluminum hydroxide |
| US20250074116A1 (en) | 2023-08-28 | 2025-03-06 | The Goodyear Tire & Rubber Company | Tire with asymmetric conductivity path |
| US20250074121A1 (en) | 2023-08-28 | 2025-03-06 | The Goodyear Tire & Rubber Company | Tire having an electrically conductive rubber strip |
| US20250109286A1 (en) | 2023-09-28 | 2025-04-03 | The Goodyear Tire & Rubber Company | All-season tire tread |
| US20250108663A1 (en) | 2023-09-29 | 2025-04-03 | The Goodyear Tire & Rubber Company | High mileage rubber composition for a radial medium truck (rmt) tire tread |
| US20250163252A1 (en) | 2023-11-21 | 2025-05-22 | The Goodyear Tire & Rubber Company | Tread composition for all-season tire |
| US20250163251A1 (en) | 2023-11-21 | 2025-05-22 | The Goodyear Tire & Rubber Company | Tread composition for all-season tire |
| US20250187374A1 (en) | 2023-12-07 | 2025-06-12 | The Goodyear Tire & Rubber Company | Rubber composition for tire tread |
| US20250250424A1 (en) | 2024-02-07 | 2025-08-07 | The Goodyear Tire & Rubber Company | Rubber composition based on multiphase dilution of composite blend |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL129664C (cg-RX-API-DMAC7.html) * | 1958-11-26 | |||
| NL246185A (cg-RX-API-DMAC7.html) * | 1958-12-08 | |||
| US3068217A (en) * | 1959-10-23 | 1962-12-11 | Shell Oil Co | Process for polymerizing diolefins in the presence of allene or dimethyl acetylene |
| US3170907A (en) | 1959-12-31 | 1965-02-23 | Bridgestone Tire Co Ltd | Production of cis-1, 4 polybutadiene with a nickel carboxylic acid salt-boron trifluoride etherate-aluminum trialkyl catalyst |
| US3725492A (en) | 1970-10-26 | 1973-04-03 | Japanese Geon Co Ltd | Process for the preparation of liquid polybutadiene |
| US4155880A (en) | 1971-11-24 | 1979-05-22 | The Goodyear Tire & Rubber Company | Catalyst composition comprising an organoaluminum compound/an organonickel compound/a hydrogen fluoride complex compound |
| US3856764A (en) * | 1971-11-24 | 1974-12-24 | Goodyear Tire & Rubber | Polymerization process |
| US3985677A (en) * | 1972-10-27 | 1976-10-12 | The Goodyear Tire & Rubber Company | Preparation of polymerization catalyst and polymerization therewith |
| US3962375A (en) | 1973-12-13 | 1976-06-08 | The Goodyear Tire & Rubber Company | Polymerization process |
| US3910869A (en) | 1974-01-31 | 1975-10-07 | Goodyear Tire & Rubber | Chemical process |
| US4383097A (en) * | 1981-08-21 | 1983-05-10 | The Goodyear Tire & Rubber Company | Molecular weight regulation of cis-1,4-polybutadiene |
| JPS5873701A (ja) * | 1981-10-28 | 1983-05-04 | Sumitomo Metal Ind Ltd | 焼入れ性及び靭性にすぐれた粉末鍛造品の製造方法 |
| JPS5873702A (ja) * | 1981-10-28 | 1983-05-04 | Sumitomo Metal Ind Ltd | 焼入れ性及び靭性にすぐれた粉末鍛造品の製造方法 |
-
1983
- 1983-04-12 CA CA000425670A patent/CA1236648A/en not_active Expired
- 1983-04-12 ZA ZA832555A patent/ZA832555B/xx unknown
- 1983-04-14 BR BR8301899A patent/BR8301899A/pt not_active IP Right Cessation
- 1983-04-21 EP EP83630071A patent/EP0093074B1/en not_active Expired
- 1983-04-21 DE DE8383630071T patent/DE3372971D1/de not_active Expired
- 1983-04-22 AU AU13869/83A patent/AU558437B2/en not_active Expired
- 1983-04-25 ES ES521805A patent/ES521805A0/es active Granted
- 1983-04-26 JP JP58073703A patent/JPS58196214A/ja active Granted
-
1995
- 1995-05-11 US US08/439,553 patent/US5698643A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1637549A1 (en) | 2004-08-30 | 2006-03-22 | The Goodyear Tire & Rubber Company | Synthesis of CIS-1,4-polybutadiene |
| US7081504B2 (en) | 2004-08-30 | 2006-07-25 | The Goodyear Tire & Rubber Company | Synthesis of 1,4-polybutadiene |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0093074A2 (en) | 1983-11-02 |
| BR8301899A (pt) | 1983-12-20 |
| US5698643A (en) | 1997-12-16 |
| DE3372971D1 (en) | 1987-09-17 |
| ZA832555B (en) | 1983-12-28 |
| JPS58196214A (ja) | 1983-11-15 |
| EP0093074B1 (en) | 1987-08-12 |
| ES8502453A1 (es) | 1985-01-01 |
| EP0093074A8 (en) | 1997-11-05 |
| AU1386983A (en) | 1983-11-03 |
| AU558437B2 (en) | 1987-01-29 |
| JPH027327B2 (cg-RX-API-DMAC7.html) | 1990-02-16 |
| ES521805A0 (es) | 1985-01-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5698643A (en) | Controlling the molecular weight of polybutadiene | |
| EP0093074A1 (en) | Controlling the molecular weight of polybutadiene | |
| US3856764A (en) | Polymerization process | |
| JP3741760B2 (ja) | シス−１，４−ポリブタジエンの分子量を減じ、そしてその加工性を改善するための技術 | |
| US4102817A (en) | Catalyst composition for the preparation of butadiene | |
| US3528957A (en) | Method of producing polybutadiene | |
| US4155880A (en) | Catalyst composition comprising an organoaluminum compound/an organonickel compound/a hydrogen fluoride complex compound | |
| US4383097A (en) | Molecular weight regulation of cis-1,4-polybutadiene | |
| EP0468914B1 (en) | Catalyst system for polymerization of 1,3-butadiene to trans-1,4-polybutadiene | |
| US20090143551A1 (en) | Nickel-based catalysts for preparing high cis 1,4-polydienes | |
| JP4208346B2 (ja) | 共役ジエンの重合における有機亜鉛及び希土類触媒系 | |
| US3962375A (en) | Polymerization process | |
| CA2037583A1 (en) | Technique for reducing the molecular weight and broadening the molecular weight distribution of high cis-1,4-polybutadiene | |
| US3525729A (en) | Process for production of polymers with controlled saturation | |
| EP0980878B1 (en) | Molecular weight regulation of cis-1,4-polybutadiene using carboxylates | |
| US3985941A (en) | Method of polymerization | |
| US5811499A (en) | Synthesis of cis-1,4-polybutadiene rubber in presence of cobalt containing catalyst system | |
| CA1236647A (en) | Preparation of high cis-1,4-polybutadiene | |
| US4983695A (en) | Molecular weight control of polybutadiene | |
| US3487063A (en) | Method of polymerizing butadiene or butadiene in mixture with other diolefins | |
| EP1325040B1 (en) | Catalyst system for high-cis polybutadiene | |
| CA1236649A (en) | Molecular weight control of polybutadiene | |
| US3734900A (en) | Polymerization of conjugated diolefins | |
| KR20010085758A (ko) | 높은 시스-1,4-폴리부타디엔 생산 공정에서 겔 감소 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |