DE1156986B - Verfahren zur Herstellung von hochmolekularen Polymerisaten durch Polymerisation von1, 3-Dienen - Google Patents
Verfahren zur Herstellung von hochmolekularen Polymerisaten durch Polymerisation von1, 3-DienenInfo
- Publication number
- DE1156986B DE1156986B DEB66199A DEB0066199A DE1156986B DE 1156986 B DE1156986 B DE 1156986B DE B66199 A DEB66199 A DE B66199A DE B0066199 A DEB0066199 A DE B0066199A DE 1156986 B DE1156986 B DE 1156986B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- benzene
- mixture
- butadiene
- aluminum
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 12
- 229920006158 high molecular weight polymer Polymers 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- 230000000379 polymerizing effect Effects 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 129
- 239000000203 mixture Substances 0.000 claims description 44
- 239000003054 catalyst Substances 0.000 claims description 34
- -1 aluminum halides Chemical class 0.000 claims description 20
- 229910052782 aluminium Inorganic materials 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- 239000008139 complexing agent Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000010941 cobalt Substances 0.000 claims description 5
- 229910017052 cobalt Inorganic materials 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- ZVHVRQOGCXCNDC-UHFFFAOYSA-N oxomethylidenenickel Chemical class O=C=[Ni] ZVHVRQOGCXCNDC-UHFFFAOYSA-N 0.000 claims description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 58
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 37
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 25
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- 229920000642 polymer Polymers 0.000 description 19
- 239000005062 Polybutadiene Substances 0.000 description 17
- 229920002857 polybutadiene Polymers 0.000 description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 229910052759 nickel Inorganic materials 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 10
- 238000003756 stirring Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000005673 monoalkenes Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 235000013844 butane Nutrition 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- AJOWDSASGHPCMO-UHFFFAOYSA-N carbonyl diiodide;cobalt Chemical compound [Co].IC(I)=O AJOWDSASGHPCMO-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 2
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- LQIIEHBULBHJKX-UHFFFAOYSA-N 2-methylpropylalumane Chemical compound CC(C)C[AlH2] LQIIEHBULBHJKX-UHFFFAOYSA-N 0.000 description 1
- SWZWGMRAEXTPOE-UHFFFAOYSA-N C(=O)(I)I.[Fe] Chemical compound C(=O)(I)I.[Fe] SWZWGMRAEXTPOE-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 241001676573 Minium Species 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- CODVACFVSVNQPY-UHFFFAOYSA-N [Co].[C] Chemical compound [Co].[C] CODVACFVSVNQPY-UHFFFAOYSA-N 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- BXILREUWHCQFES-UHFFFAOYSA-K aluminum;trichloride;hydrochloride Chemical compound [Al+3].Cl.[Cl-].[Cl-].[Cl-] BXILREUWHCQFES-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- YMFAWOSEDSLYSZ-UHFFFAOYSA-N carbon monoxide;cobalt Chemical group [Co].[Co].[Co].[Co].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] YMFAWOSEDSLYSZ-UHFFFAOYSA-N 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- IFRJAXAQXBGUTF-UHFFFAOYSA-N cobalt 2-phenylethynylbenzene Chemical compound [Co].[Co].C1(=CC=CC=C1)C#CC1=CC=CC=C1 IFRJAXAQXBGUTF-UHFFFAOYSA-N 0.000 description 1
- UMYVESYOFCWRIW-UHFFFAOYSA-N cobalt;methanone Chemical class O=C=[Co] UMYVESYOFCWRIW-UHFFFAOYSA-N 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N methyl heptene Natural products CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- WNFSFUSCVXIYGN-UHFFFAOYSA-N phenylaluminum Chemical compound [Al]C1=CC=CC=C1 WNFSFUSCVXIYGN-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE629111D BE629111A (enrdf_load_stackoverflow) | 1962-03-03 | ||
| NL289530D NL289530A (enrdf_load_stackoverflow) | 1962-03-03 | ||
| DEB66199A DE1156986B (de) | 1962-03-03 | 1962-03-03 | Verfahren zur Herstellung von hochmolekularen Polymerisaten durch Polymerisation von1, 3-Dienen |
| CH205463A CH424272A (de) | 1962-03-03 | 1963-02-19 | Verfahren zur Herstellung von hochmolekularen Polymeren aus 1,3-Dienen |
| GB740563A GB1027867A (enrdf_load_stackoverflow) | 1962-03-03 | 1963-02-25 | |
| AT163563A AT242362B (de) | 1962-03-03 | 1963-03-01 | Verfahren zur Herstellung von hochmolekularen Polymeren aus 1,3-Dienen |
| SE229963A SE321565B (enrdf_load_stackoverflow) | 1962-03-03 | 1963-03-01 | |
| FR926638A FR1353189A (fr) | 1962-03-03 | 1963-03-02 | Procédé pour la production de polymères de diènes-1-3, à poids moléculaire élevé |
| CH270467A CH463065A (de) | 1962-03-03 | 1967-02-21 | Schalkörper zur Verwendung als verlorene Schalung in Stahlbetonrippendecken |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB66199A DE1156986B (de) | 1962-03-03 | 1962-03-03 | Verfahren zur Herstellung von hochmolekularen Polymerisaten durch Polymerisation von1, 3-Dienen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1156986B true DE1156986B (de) | 1963-11-07 |
Family
ID=6975044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB66199A Pending DE1156986B (de) | 1962-03-03 | 1962-03-03 | Verfahren zur Herstellung von hochmolekularen Polymerisaten durch Polymerisation von1, 3-Dienen |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT242362B (enrdf_load_stackoverflow) |
| BE (1) | BE629111A (enrdf_load_stackoverflow) |
| CH (1) | CH424272A (enrdf_load_stackoverflow) |
| DE (1) | DE1156986B (enrdf_load_stackoverflow) |
| GB (1) | GB1027867A (enrdf_load_stackoverflow) |
| NL (1) | NL289530A (enrdf_load_stackoverflow) |
| SE (1) | SE321565B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1292847B (de) * | 1965-08-28 | 1969-04-17 | Basf Ag | Verfahren zur Herstellung von 1, 3-Dien-Mischpolymerisaten |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2488556B1 (en) | 2009-10-14 | 2013-09-11 | Bridgestone Corporation | Processes for preparation of cyclic acyclic diene copolymer and rubber composition |
-
0
- NL NL289530D patent/NL289530A/xx unknown
- BE BE629111D patent/BE629111A/xx unknown
-
1962
- 1962-03-03 DE DEB66199A patent/DE1156986B/de active Pending
-
1963
- 1963-02-19 CH CH205463A patent/CH424272A/de unknown
- 1963-02-25 GB GB740563A patent/GB1027867A/en not_active Expired
- 1963-03-01 SE SE229963A patent/SE321565B/xx unknown
- 1963-03-01 AT AT163563A patent/AT242362B/de active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1292847B (de) * | 1965-08-28 | 1969-04-17 | Basf Ag | Verfahren zur Herstellung von 1, 3-Dien-Mischpolymerisaten |
Also Published As
| Publication number | Publication date |
|---|---|
| BE629111A (enrdf_load_stackoverflow) | |
| AT242362B (de) | 1965-09-10 |
| NL289530A (enrdf_load_stackoverflow) | |
| GB1027867A (enrdf_load_stackoverflow) | 1966-04-27 |
| CH424272A (de) | 1966-11-15 |
| SE321565B (enrdf_load_stackoverflow) | 1970-03-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0222189B1 (de) | Verfahren und Katalysator zur Herstellung von syndiotaktischem 1,2-Polybutadien | |
| DE2731067C3 (de) | Verfahren zur Herstellung von Polybutadien mit einem hohen Gehalt an Monomereneinheiten in cis-1,4- Struktur | |
| DE1128143B (de) | Verfahren zur Polymerisation von aliphatischen konjugierten Diolefinen | |
| DE1292853B (de) | Verfahren zur Herstellung von fluessigen, niedermolekularen ungesaettigten Polymeren | |
| DE2357001A1 (de) | Verfahren zur isomerisation niedriger butadienpolymere | |
| DE1148384B (de) | Verfahren zur Polymerisation von Butadien | |
| EP0312928A1 (de) | Verzweigte Copolymerisate und Verfahren zu ihrer Herstellung | |
| DE1133548B (de) | Verfahren zum Polymerisieren von konjugierten Diolefinen mit wenigstens einer endstaendigen Vinyldoppelbindung | |
| DE1241119B (de) | Verfahren zur Herstellung von niedermolekularen, fluessigen, ungesaettigten Polymeren | |
| DE1720320A1 (de) | Verfahren zur katalytischen Hydrierung von Polymeren | |
| DE1156986B (de) | Verfahren zur Herstellung von hochmolekularen Polymerisaten durch Polymerisation von1, 3-Dienen | |
| DE2016128A1 (de) | Verfahren zur Isomerisierung von 5-Vinylbicyclo eckige Klammer auf 2.2.1 eckige Klammer zu hept-2-enen | |
| DE2131355A1 (de) | Verfahren zur herstellung von copolyalkenameren | |
| DE1137007B (de) | Verfahren zur Herstellung niederer, fluessiger Oligomerer aus 1, 3-Dienen | |
| DD236321A1 (de) | Verfahren zur selektiven butadienpolymerisation aus c tief 4 fraktion | |
| DE1251535B (de) | Verfahren zur Herstellung von Butadienpolymensaten | |
| DE2431258A1 (de) | Verfahren zur herstellung von polybutadien | |
| DE1645467B2 (de) | Verfahren zu der herstellung von hochmolekularen polymeren konjugierter diene | |
| DE1252418B (de) | Verfahren zur Herstellung von Butadienpol-ymensaten | |
| DE1239479B (de) | Verfahren zur Herstellung von hochmolekularen Polymerisaten durch Polymerisation von 1, 3-Dienen | |
| DE1251033B (de) | I Verfahren zur katalytischen Polymerisation oder Mischpolymerisation von Diolefmen | |
| DE2232767A1 (de) | Neues verfahren zur herstellung von wasserstoffhaltigen polymeren aus konjugierten diolefinen | |
| DE1181425B (de) | Verfahren zur Herstellung von Polymerisaten aus Butadien-(1, 3) | |
| DE1793237C3 (de) | Nickel-pi-Allylverbindungen, Verfahren zu ihrer Herstellung sowie deren Verwendung | |
| DE1570159C3 (de) | Reif enlauff lächenmischun gen |