DE2447203C3 - Verfahren zur Herstellung von Polybutadien - Google Patents
Verfahren zur Herstellung von PolybutadienInfo
- Publication number
- DE2447203C3 DE2447203C3 DE2447203A DE2447203A DE2447203C3 DE 2447203 C3 DE2447203 C3 DE 2447203C3 DE 2447203 A DE2447203 A DE 2447203A DE 2447203 A DE2447203 A DE 2447203A DE 2447203 C3 DE2447203 C3 DE 2447203C3
- Authority
- DE
- Germany
- Prior art keywords
- double bonds
- polybutadienes
- trans
- component
- vinyl
- 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
- 238000000034 method Methods 0.000 title claims description 28
- 230000008569 process Effects 0.000 title claims description 14
- 229920002857 polybutadiene Polymers 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000005062 Polybutadiene Substances 0.000 title claims description 3
- -1 aluminum halide Chemical class 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- 229920001971 elastomer Polymers 0.000 claims description 4
- 239000005060 rubber Substances 0.000 claims description 4
- 150000008282 halocarbons Chemical class 0.000 claims description 3
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000010626 work up procedure Methods 0.000 claims description 3
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003003 phosphines Chemical class 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 239000011954 Ziegler–Natta catalyst Substances 0.000 claims 1
- 230000002411 adverse Effects 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- 239000010941 cobalt Substances 0.000 claims 1
- FJDJVBXSSLDNJB-LNTINUHCSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FJDJVBXSSLDNJB-LNTINUHCSA-N 0.000 claims 1
- 230000009918 complex formation Effects 0.000 claims 1
- 239000002815 homogeneous catalyst Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000005470 impregnation Methods 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 239000003973 paint Substances 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- 150000003018 phosphorus compounds Chemical class 0.000 claims 1
- 229920002589 poly(vinylethylene) polymer Polymers 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
- 230000004048 modification Effects 0.000 description 7
- 238000012986 modification Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000009826 distribution Methods 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 4
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- GWESVXSMPKAFAS-UHFFFAOYSA-N Isopropylcyclohexane Chemical compound CC(C)C1CCCCC1 GWESVXSMPKAFAS-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- ZUBZATZOEPUUQF-UHFFFAOYSA-N isononane Chemical compound CCCCCCC(C)C ZUBZATZOEPUUQF-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane Chemical compound CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- ADQGXUHCBBVRGM-UHFFFAOYSA-N trinaphthalen-1-yl phosphite Chemical class C1=CC=C2C(OP(OC=3C4=CC=CC=C4C=CC=3)OC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ADQGXUHCBBVRGM-UHFFFAOYSA-N 0.000 description 2
- DAZUWKNHFLGZSN-UHFFFAOYSA-N tris(2-phenylphenyl) phosphite Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1OP(OC=1C(=CC=CC=1)C=1C=CC=CC=1)OC1=CC=CC=C1C1=CC=CC=C1 DAZUWKNHFLGZSN-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SGVYKUFIHHTIFL-UHFFFAOYSA-N Isobutylhexyl Natural products CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 241000238633 Odonata Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 description 1
- BEWYHVAWEKZDPP-UHFFFAOYSA-N camphane Natural products C1CC2(C)CCC1C2(C)C BEWYHVAWEKZDPP-UHFFFAOYSA-N 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 1
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229930006728 pinane Natural products 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- BEYZCUUFIOSILA-UHFFFAOYSA-N tris(2,4,6-tribromophenyl) phosphite Chemical compound BrC1=CC(Br)=CC(Br)=C1OP(OC=1C(=CC(Br)=CC=1Br)Br)OC1=C(Br)C=C(Br)C=C1Br BEYZCUUFIOSILA-UHFFFAOYSA-N 0.000 description 1
- KXDRRFQARLPIBW-UHFFFAOYSA-N tris(2-chlorophenyl) phosphite Chemical compound ClC1=CC=CC=C1OP(OC=1C(=CC=CC=1)Cl)OC1=CC=CC=C1Cl KXDRRFQARLPIBW-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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2447203A DE2447203C3 (de) | 1974-10-03 | 1974-10-03 | Verfahren zur Herstellung von Polybutadien |
| US05/530,550 US3966697A (en) | 1974-10-03 | 1974-12-09 | Production of high-vinyl group, high-molecular weight unsaturated hydrocarbon polymers |
| SU2084825A SU533326A3 (ru) | 1973-12-12 | 1974-12-10 | Катализаторна система дл получени ненасыщенных углеводородных полимеров |
| FR7529787A FR2286837A1 (fr) | 1974-10-03 | 1975-09-29 | Procede de preparation de produits de polymerisation insatures d'hydrocarbures contenant une proportion accrue de groupes vinyle ou de groupes vinyle substitues |
| IT51590/75A IT1047652B (it) | 1974-10-03 | 1975-10-01 | Procedimento per produrre polimeridi idrocarburi insaturi con altotenore in gruppi vinilici |
| CA236,909A CA1055197A (en) | 1974-10-03 | 1975-10-02 | Process for producing unsaturated hydrocarbon polymerizates with increased portion of vinyl groups or substituted vinyl groups |
| JP50118304A JPS5161590A (en) | 1974-10-03 | 1975-10-02 | Biniru aruiha chikansaretabiniruki no seibunnoooi fuhowatankasuisojugotai no seizohoho |
| NL7511611A NL7511611A (nl) | 1974-10-03 | 1975-10-02 | Werkwijze voor de bereiding van onverzadigde kool- waterstofpolymeren met een groot gehalte aan vinyl- groepen respectievelijk gesubstitueerde vinylgroe- pen. |
| BE160656A BE834150A (fr) | 1974-10-03 | 1975-10-02 | Procede de production de polymeres d'hydrocarbures non satures a teneur accrue en radicaux vinyle ou vinyle substitues |
| GB40291/75A GB1513879A (en) | 1974-10-03 | 1975-10-02 | Process for the production of high molecular weight unsaturated hydrocarbon polymers having an increased proportion of vinyl groups and/or substituted vinyl groups |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2447203A DE2447203C3 (de) | 1974-10-03 | 1974-10-03 | Verfahren zur Herstellung von Polybutadien |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2447203A1 DE2447203A1 (de) | 1976-04-15 |
| DE2447203B2 DE2447203B2 (de) | 1981-05-07 |
| DE2447203C3 true DE2447203C3 (de) | 1982-03-18 |
Family
ID=5927430
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2447203A Expired DE2447203C3 (de) | 1973-12-12 | 1974-10-03 | Verfahren zur Herstellung von Polybutadien |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3966697A (https=) |
| JP (1) | JPS5161590A (https=) |
| BE (1) | BE834150A (https=) |
| CA (1) | CA1055197A (https=) |
| DE (1) | DE2447203C3 (https=) |
| FR (1) | FR2286837A1 (https=) |
| GB (1) | GB1513879A (https=) |
| IT (1) | IT1047652B (https=) |
| NL (1) | NL7511611A (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1108798A (en) * | 1978-05-08 | 1981-09-08 | Evalds Lasis | Low benzene butadiene polymerization |
| US4303769A (en) * | 1978-08-22 | 1981-12-01 | The B. F. Goodrich Company | Process for preparing substantially gel-free cis-1,4-polybutadiene |
| DE2911262A1 (de) * | 1979-03-22 | 1980-10-02 | Bayer Ag | Katalysator, dessen herstellung und verfahren zur polymerisation von butadien |
| JPS6185414A (ja) * | 1984-10-02 | 1986-05-01 | Ube Ind Ltd | ポリプタジエンの製造方法 |
| JPS6283594A (ja) * | 1985-10-08 | 1987-04-17 | ヤンマーディーゼル株式会社 | エンジンヒ−トポンプの防振装置 |
| JP3463811B2 (ja) * | 1991-04-24 | 2003-11-05 | Ｊｓｒ株式会社 | ブタジエン系重合体の製造方法 |
| US6399732B2 (en) | 1998-10-14 | 2002-06-04 | Bridgestone Corporation | Preparation of conjugated diene polymers by using an iron-based catalayst system |
| ITMI20122199A1 (it) | 2012-12-20 | 2014-06-21 | Versalis Spa | Procedimento per la preparazione di (co)polimeri di dieni coniugati in presenza di un sistema catalitico comprendente un complesso bis-imminico di cobalto |
| ITMI20122203A1 (it) | 2012-12-20 | 2014-06-21 | Versalis Spa | Procedimento per la preparazione di (co)polimeri di dieni coniugati in presenza di un sistema catalitico comprendente un complesso osso-azotato di cobalto |
| ITMI20122201A1 (it) | 2012-12-20 | 2014-06-21 | Versalis Spa | Complesso osso-azotato di cobalto, sistema catalitico comprendente detto complesso osso-azotato e procedimento per la (co)polimerizzazione di dieni coniugati |
| ITMI20122206A1 (it) | 2012-12-20 | 2014-06-21 | Versalis Spa | Procedimento per la preparazione di (co)polimeri di dieni coniugati in presenza di un sistema catalitico comprendente un complesso bis-immino-piridinico di cobalto |
| ITMI20131830A1 (it) | 2013-11-05 | 2015-05-06 | Versalis Spa | Polibutadieni di-blocco stereoregolari a struttura 1,4-cis/1,2 sindiotattica da polimerizzazione stereospecifica |
| ITMI20131828A1 (it) | 2013-11-05 | 2015-05-06 | Versalis Spa | Polibutadieni di-blocco stereoregolari a struttura 1,4-cis/1,2 sindiotattica da polimerizzazione stereospecifica |
| IT201600105530A1 (it) | 2016-10-20 | 2018-04-20 | Versalis Spa | Procedimento per la preparazione di polibutadiene 1,2 sindiotattico in presenza di un sistema catalitico comprendente un complesso piridilico di ferro |
| EP3348589B1 (de) | 2017-01-16 | 2019-08-07 | Evonik Degussa GmbH | Polybutadiene, deren herstellung und verwendung |
| IT202000028823A1 (it) | 2020-11-27 | 2022-05-27 | Consiglio Nazionale Ricerche | Copolimeri dienici a stereoblocchi e relativo processo di preparazione. |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL235967A (https=) * | 1958-02-11 | |||
| BE595548A (https=) * | 1959-09-30 | |||
| US3040016A (en) * | 1960-03-28 | 1962-06-19 | Shell Oil Co | Polymerization process |
| NL266379A (https=) * | 1960-06-27 | |||
| US3480607A (en) * | 1965-12-03 | 1969-11-25 | Phillips Petroleum Co | Polymerization |
| GB1158296A (en) * | 1966-09-26 | 1969-07-16 | Japan Synthetic Rubber Co Ltd | Unsaturated Hydrocarbon Polymers |
| US3522332A (en) * | 1967-06-02 | 1970-07-28 | Japan Synthetic Rubber Co Ltd | Process for the preparation of 1,2-polybutadiene |
| JPS5618006B2 (https=) * | 1974-06-21 | 1981-04-25 |
-
1974
- 1974-10-03 DE DE2447203A patent/DE2447203C3/de not_active Expired
- 1974-12-09 US US05/530,550 patent/US3966697A/en not_active Expired - Lifetime
-
1975
- 1975-09-29 FR FR7529787A patent/FR2286837A1/fr active Granted
- 1975-10-01 IT IT51590/75A patent/IT1047652B/it active
- 1975-10-02 NL NL7511611A patent/NL7511611A/xx not_active Application Discontinuation
- 1975-10-02 JP JP50118304A patent/JPS5161590A/ja active Granted
- 1975-10-02 GB GB40291/75A patent/GB1513879A/en not_active Expired
- 1975-10-02 BE BE160656A patent/BE834150A/xx not_active IP Right Cessation
- 1975-10-02 CA CA236,909A patent/CA1055197A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2447203A1 (de) | 1976-04-15 |
| CA1055197A (en) | 1979-05-22 |
| NL7511611A (nl) | 1976-04-06 |
| JPS5161590A (en) | 1976-05-28 |
| FR2286837A1 (fr) | 1976-04-30 |
| DE2447203B2 (de) | 1981-05-07 |
| US3966697A (en) | 1976-06-29 |
| IT1047652B (it) | 1980-10-20 |
| FR2286837B1 (https=) | 1979-09-07 |
| JPS5650894B2 (https=) | 1981-12-02 |
| BE834150A (fr) | 1976-02-02 |
| GB1513879A (en) | 1978-06-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2447203C3 (de) | Verfahren zur Herstellung von Polybutadien | |
| EP0707017B1 (de) | Verfahren zur Herstellung von mittels Nd-Katalysatoren polymerisierten Dienkautschuken mit niedrigem cold-flow und geringem Eigengeruch | |
| DE2731067C3 (de) | Verfahren zur Herstellung von Polybutadien mit einem hohen Gehalt an Monomereneinheiten in cis-1,4- Struktur | |
| DE1720998C2 (de) | Verfahren zur Herstellung von Polybutadien mit einem hohen Gehalt an Vinylseitengruppen | |
| EP0222189B1 (de) | Verfahren und Katalysator zur Herstellung von syndiotaktischem 1,2-Polybutadien | |
| DE69004712T2 (de) | Verfahren zur Herstellung von Polybutadien mit verbesserter Verarbeitkeit. | |
| WO2011045393A1 (de) | Neodym-katalysierte polybutadiene | |
| DE2361782C3 (de) | Verfahren zur herstellung von niedermolekularem Polybutadien | |
| DE1420698B2 (de) | Verfahren zur Herstellung eines Dienmischpolymerisats | |
| DE2117995C2 (de) | Diskontinuierliches Verfahren zur Herstellung von statistischen Copolymerisaten aus einem aliphatischen konjugierten Dien und vinylaromatischen Verbindungen | |
| EP0016392B1 (de) | Katalysator, dessen Herstellung und Verfahren zur Polymerisation von Butadien | |
| DE2163542C3 (de) | Polybutadien, Verfahren zu seiner Herstellung und Verwendung desselben | |
| DE1104703B (de) | Verfahren zur Herstellung von 1, 3-Butadienpolymeren | |
| DE1133548B (de) | Verfahren zum Polymerisieren von konjugierten Diolefinen mit wenigstens einer endstaendigen Vinyldoppelbindung | |
| DE1104188B (de) | Verfahren zum Herstellen eines kautschukartigen Polymeren | |
| EP0032167A1 (de) | Verfahren zur Herstellung von Reaktionsprodukten aus konjugierten Diolefinen und aromatischen Kohlenwasserstoffen | |
| DE1299865B (de) | Verfahren zur Polymerisation von konjugierten Dien-Kohlenwasserstoffen | |
| DE1169675B (de) | Verfahren zur Polymerisation von Isopren oder Butadien | |
| DE2350941A1 (de) | Verfahren zur polymerisation von butadien und butadien in mischung mit anderen diolefinen | |
| DE1933620C3 (de) | Verfahren zur Herstellung eines Polybutadien | |
| DE2036395C3 (de) | Verfahren zur Gewinnung von elastomeren Polymerisaten oder Copolymerisaten aus ihrer Lösung | |
| DE1251033B (de) | I Verfahren zur katalytischen Polymerisation oder Mischpolymerisation von Diolefmen | |
| DE1745227C (de) | Verfahren zur katalytischen Polymerisation von 1,3-Butadien | |
| DE1520479C (de) | Verfahren zur Herstellung von eis 1,4 Polybutadien | |
| DE2644439C2 (de) | Verfahren zur Herstellung von modifiziertem und stabilisiertem synthetischem cis-1,4-Polyisopren |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |