CA2719728C - Process for the preparation of branched polybutadiene with a high content of 1,4-cis units - Google Patents
Process for the preparation of branched polybutadiene with a high content of 1,4-cis units Download PDFInfo
- Publication number
- CA2719728C CA2719728C CA2719728A CA2719728A CA2719728C CA 2719728 C CA2719728 C CA 2719728C CA 2719728 A CA2719728 A CA 2719728A CA 2719728 A CA2719728 A CA 2719728A CA 2719728 C CA2719728 C CA 2719728C
- Authority
- CA
- Canada
- Prior art keywords
- process according
- aluminium
- molar ratio
- bond
- neodymium
- 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.)
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- 238000000034 method Methods 0.000 title claims abstract description 59
- 230000008569 process Effects 0.000 title claims abstract description 53
- 229920002857 polybutadiene Polymers 0.000 title claims abstract description 42
- 239000005062 Polybutadiene Substances 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 27
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 46
- -1 alkyl compound Chemical class 0.000 claims abstract description 38
- 229910052779 Neodymium Inorganic materials 0.000 claims abstract description 36
- 239000002904 solvent Substances 0.000 claims abstract description 33
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 23
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims abstract description 21
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 18
- 230000003197 catalytic effect Effects 0.000 claims abstract description 17
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 10
- 150000007942 carboxylates Chemical class 0.000 claims abstract description 7
- 238000011065 in-situ storage Methods 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 31
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 18
- 239000004411 aluminium Substances 0.000 claims description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 239000012320 chlorinating reagent Substances 0.000 claims description 3
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 3
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims description 2
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 claims description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 4
- VCDPEVKSRRTMJM-UHFFFAOYSA-N aluminum(2+) monohydride Chemical compound [AlH+2] VCDPEVKSRRTMJM-UHFFFAOYSA-N 0.000 claims 3
- 229910000091 aluminium hydride Inorganic materials 0.000 claims 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 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 53
- 230000015572 biosynthetic process Effects 0.000 description 22
- 230000009021 linear effect Effects 0.000 description 21
- 238000009826 distribution Methods 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 18
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 17
- 235000010210 aluminium Nutrition 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 229910052759 nickel Inorganic materials 0.000 description 7
- 239000004033 plastic Substances 0.000 description 7
- 229920003023 plastic Polymers 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 230000010355 oscillation Effects 0.000 description 6
- 230000000750 progressive effect Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 229920002521 macromolecule Polymers 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 238000000569 multi-angle light scattering Methods 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- 229910052719 titanium Inorganic materials 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002168 alkylating agent Substances 0.000 description 4
- 229940100198 alkylating agent Drugs 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002808 molecular sieve Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000006722 reduction reaction Methods 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
- 241001441571 Hiodontidae Species 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 229920005669 high impact polystyrene Polymers 0.000 description 3
- 239000004797 high-impact polystyrene Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000007425 progressive decline Effects 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000002596 correlated effect Effects 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 1
- 241001556567 Acanthamoeba polyphaga mimivirus Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 150000001206 Neodymium Chemical class 0.000 description 1
- 101100202924 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) tsp-2 gene Proteins 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- JSSFTRRPZVXBMS-UHFFFAOYSA-N [Nd+] Chemical compound [Nd+] JSSFTRRPZVXBMS-UHFFFAOYSA-N 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000002844 continuous effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- VTZJFPSWNQFPCQ-UHFFFAOYSA-N dibutylaluminum Chemical compound CCCC[Al]CCCC VTZJFPSWNQFPCQ-UHFFFAOYSA-N 0.000 description 1
- CPDVHGLWIFENDJ-UHFFFAOYSA-N dihexylalumane Chemical compound C(CCCCC)[AlH]CCCCCC CPDVHGLWIFENDJ-UHFFFAOYSA-N 0.000 description 1
- XOCWTYIVWYOSGQ-UHFFFAOYSA-N dipropylalumane Chemical compound C(CC)[AlH]CCC XOCWTYIVWYOSGQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- VALAJCQQJWINGW-UHFFFAOYSA-N tri(propan-2-yl)alumane Chemical compound CC(C)[Al](C(C)C)C(C)C VALAJCQQJWINGW-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
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C08F36/06—Butadiene
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/54—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with other compounds thereof
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/54—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with other compounds thereof
- C08F4/545—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with other compounds thereof rare earths being present, e.g. triethylaluminium + neodymium octanoate
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000570A ITMI20080570A1 (it) | 2008-04-02 | 2008-04-02 | Procedimento per la preparazione di polibutadiene ramificato ad alto contenuto in unita' 1,4-cis |
| ITMI2008A000570 | 2008-04-02 | ||
| PCT/EP2009/002218 WO2009121516A1 (en) | 2008-04-02 | 2009-03-19 | Process for the preparation of branched polybutadiene with a high content of 1,4-cis units |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2719728A1 CA2719728A1 (en) | 2009-10-08 |
| CA2719728C true CA2719728C (en) | 2017-09-12 |
Family
ID=40296838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2719728A Active CA2719728C (en) | 2008-04-02 | 2009-03-19 | Process for the preparation of branched polybutadiene with a high content of 1,4-cis units |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8664344B2 (enExample) |
| EP (1) | EP2260063B1 (enExample) |
| JP (1) | JP5520284B2 (enExample) |
| KR (1) | KR101576315B1 (enExample) |
| CN (1) | CN102037027B (enExample) |
| BR (1) | BRPI0909393B1 (enExample) |
| CA (1) | CA2719728C (enExample) |
| ES (1) | ES2449597T3 (enExample) |
| IT (1) | ITMI20080570A1 (enExample) |
| MX (1) | MX2010010874A (enExample) |
| PL (1) | PL2260063T3 (enExample) |
| SI (1) | SI2260063T1 (enExample) |
| TW (1) | TWI475036B (enExample) |
| WO (1) | WO2009121516A1 (enExample) |
| ZA (1) | ZA201006896B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2363303A1 (de) * | 2010-02-19 | 2011-09-07 | LANXESS Deutschland GmbH | Bimodales NdBR |
| CN104136238B (zh) * | 2012-02-29 | 2017-07-04 | 盛禧奥欧洲有限责任公司 | 产生二烯聚合物的方法 |
| ITMI20120808A1 (it) * | 2012-05-11 | 2013-11-12 | Versalis Spa | "procedimento per la preparazione di polibutadiene ramificato ad alto contenuto in unita' 1,4-cis" |
| EP2676968A1 (de) * | 2012-06-18 | 2013-12-25 | LANXESS Deutschland GmbH | Hoch Mooney NdBR mit Mooneysprung |
| JP6268119B2 (ja) * | 2015-04-09 | 2018-01-24 | 株式会社ブリヂストン | ポリブタジエン及びその製造方法、並びにゴム組成物及びタイヤ |
| JP5939333B1 (ja) * | 2015-04-28 | 2016-06-22 | 宇部興産株式会社 | ジエン系ゴムの製造方法 |
| CN107793534A (zh) * | 2016-08-30 | 2018-03-13 | 中国石油化工股份有限公司 | 一种顺丁橡胶的制备方法 |
| IT201800005841A1 (it) * | 2018-05-30 | 2019-11-30 | Procedimento per la preparazione di copolimeri random butadiene-isoprene ad elevato contenuto di unita’ 1,4-cis | |
| KR102890269B1 (ko) * | 2020-09-25 | 2025-11-25 | 주식회사 엘지화학 | 네오디뮴 촉매화 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| EP4504805A1 (en) * | 2022-04-08 | 2025-02-12 | ARLANXEO Deutschland GmbH | Branched modified diene rubbers |
| WO2025093385A1 (en) | 2023-10-30 | 2025-05-08 | Arlanxeo Deutschland Gmbh | Oil-extended polybutadiene polymer |
| CN119735727A (zh) * | 2024-12-18 | 2025-04-01 | 怡维怡橡胶研究院有限公司 | 稀土催化剂的制备方法和应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1191612B (it) * | 1985-05-15 | 1988-03-23 | Enichem Elastomers | Procedimento migliorato per la polimerizzazione o copolimerizzazione del butadiene |
| US5428119A (en) * | 1993-11-09 | 1995-06-27 | Polysar Rubber Corporation | Process for polybutadiene production using catalyst with high activity |
| US6111082A (en) * | 1998-04-17 | 2000-08-29 | Rhodia Rare Earths Inc. | Stable concentrated rare earth carboxylate liquids |
| BR9902609B1 (pt) * | 1999-05-27 | 2010-08-10 | processo para a preparação de neodecanoato de neodìmio, processo para a preparação de um sistema catalìtico homogêneo de coordenação, processo para polimerização em solução para a preparação de polibutadieno de alto teor de ligações 1,4-cis. | |
| KR100352764B1 (ko) * | 2000-03-16 | 2002-09-16 | 금호석유화학 주식회사 | 신규한 단분자 니오디뮴 카르복실레이트 화합물 및 이를포함하는 디엔 중합용 촉매 |
| ITMI20022711A1 (it) * | 2002-12-20 | 2004-06-21 | Polimeri Europa Spa | Procedimento per la preparazione di polidieni ramificati in presenza di catalizzatori a base di terre rare. |
| ITMI20040076A1 (it) * | 2004-01-22 | 2004-04-22 | Polimeri Europa Spa | Procedimento per la preparazione di polibutadiene a basso grado di ranificazione |
| ITMI20042022A1 (it) * | 2004-10-25 | 2005-01-25 | Polimeri Europa Spa | Processo per la preparazione di polibutadiene a basso grado di ramificazione |
| ITMI20060619A1 (it) * | 2006-03-31 | 2007-10-01 | Polimeri Europa Spa | Processo per la purificazione di carbossilati lantanidi |
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2008
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- 2009-03-19 MX MX2010010874A patent/MX2010010874A/es active IP Right Grant
- 2009-03-19 SI SI200930864T patent/SI2260063T1/sl unknown
- 2009-03-19 BR BRPI0909393-1A patent/BRPI0909393B1/pt active IP Right Grant
- 2009-03-19 EP EP09727457.5A patent/EP2260063B1/en active Active
- 2009-03-19 JP JP2011502264A patent/JP5520284B2/ja active Active
- 2009-03-19 KR KR1020107024637A patent/KR101576315B1/ko active Active
- 2009-03-19 PL PL09727457T patent/PL2260063T3/pl unknown
- 2009-03-19 WO PCT/EP2009/002218 patent/WO2009121516A1/en not_active Ceased
- 2009-03-19 ES ES09727457.5T patent/ES2449597T3/es active Active
- 2009-03-19 CN CN200980118025.9A patent/CN102037027B/zh active Active
- 2009-03-19 US US12/935,780 patent/US8664344B2/en active Active
- 2009-03-19 CA CA2719728A patent/CA2719728C/en active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| US8664344B2 (en) | 2014-03-04 |
| EP2260063A1 (en) | 2010-12-15 |
| MX2010010874A (es) | 2011-04-26 |
| WO2009121516A1 (en) | 2009-10-08 |
| US20110112261A1 (en) | 2011-05-12 |
| PL2260063T3 (pl) | 2014-09-30 |
| EP2260063B1 (en) | 2013-12-11 |
| TWI475036B (zh) | 2015-03-01 |
| CN102037027A (zh) | 2011-04-27 |
| KR20110008074A (ko) | 2011-01-25 |
| ES2449597T3 (es) | 2014-03-20 |
| JP2011516642A (ja) | 2011-05-26 |
| SI2260063T1 (sl) | 2014-04-30 |
| ITMI20080570A1 (it) | 2009-10-03 |
| BRPI0909393B1 (pt) | 2019-05-14 |
| ZA201006896B (en) | 2011-11-30 |
| CA2719728A1 (en) | 2009-10-08 |
| KR101576315B1 (ko) | 2015-12-09 |
| TW200951152A (en) | 2009-12-16 |
| BRPI0909393A2 (pt) | 2015-12-22 |
| JP5520284B2 (ja) | 2014-06-11 |
| CN102037027B (zh) | 2014-02-26 |
| HK1147507A1 (en) | 2011-08-12 |
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