NO134620B - - Google Patents
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- Publication number
- NO134620B NO134620B NO1300/72A NO130072A NO134620B NO 134620 B NO134620 B NO 134620B NO 1300/72 A NO1300/72 A NO 1300/72A NO 130072 A NO130072 A NO 130072A NO 134620 B NO134620 B NO 134620B
- Authority
- NO
- Norway
- Prior art keywords
- temperature
- catalyst
- autoclave
- butadiene
- crystallization
- Prior art date
Links
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 52
- 229920000642 polymer Polymers 0.000 claims description 46
- 239000003054 catalyst Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 20
- 238000006116 polymerization reaction Methods 0.000 claims description 20
- 238000002425 crystallisation Methods 0.000 claims description 15
- 230000008025 crystallization Effects 0.000 claims description 15
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000002844 melting Methods 0.000 claims description 11
- 230000008018 melting Effects 0.000 claims description 11
- 150000002902 organometallic compounds Chemical class 0.000 claims description 10
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 claims description 10
- 229910017052 cobalt Inorganic materials 0.000 claims description 8
- 239000010941 cobalt Substances 0.000 claims description 8
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 8
- 230000000737 periodic effect Effects 0.000 claims description 7
- 229920002521 macromolecule Polymers 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- NLLZTRMHNHVXJJ-UHFFFAOYSA-J titanium tetraiodide Chemical compound I[Ti](I)(I)I NLLZTRMHNHVXJJ-UHFFFAOYSA-J 0.000 claims description 5
- -1 alkyl aluminum halide Chemical class 0.000 claims description 4
- 230000006698 induction Effects 0.000 claims description 4
- 230000007704 transition Effects 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000002638 heterogeneous catalyst Substances 0.000 claims description 2
- 238000010586 diagram Methods 0.000 claims 2
- 150000001868 cobalt Chemical class 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
- 238000006243 chemical reaction Methods 0.000 description 18
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 16
- 229920002857 polybutadiene Polymers 0.000 description 14
- 239000005062 Polybutadiene Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 3
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 239000005373 porous glass Substances 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229910000152 cobalt phosphate Inorganic materials 0.000 description 2
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 2
- ZBDSFTZNNQNSQM-UHFFFAOYSA-H cobalt(2+);diphosphate Chemical compound [Co+2].[Co+2].[Co+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O ZBDSFTZNNQNSQM-UHFFFAOYSA-H 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 150000004763 sulfides Chemical class 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021585 Nickel(II) bromide Inorganic materials 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 229940044175 cobalt sulfate Drugs 0.000 description 1
- 229910000361 cobalt sulfate Inorganic materials 0.000 description 1
- DXZRXGASEKGJJE-UHFFFAOYSA-N cobalt;phthalic acid Chemical compound [Co].OC(=O)C1=CC=CC=C1C(O)=O DXZRXGASEKGJJE-UHFFFAOYSA-N 0.000 description 1
- 239000012809 cooling fluid Substances 0.000 description 1
- 239000012967 coordination catalyst Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 125000004334 oxygen containing inorganic group Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000052 poly(p-xylylene) Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- VRRFSFYSLSPWQY-UHFFFAOYSA-N sulfanylidenecobalt Chemical compound [Co]=S VRRFSFYSLSPWQY-UHFFFAOYSA-N 0.000 description 1
- BZWKPZBXAMTXNQ-UHFFFAOYSA-N sulfurocyanidic acid Chemical class OS(=O)(=O)C#N BZWKPZBXAMTXNQ-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712118261 DE2118261A1 (de) | 1971-04-15 | 1971-04-15 | Neue N-haltige Bicyclen, deren Säureadditionssalze sowie Verfahren zu deren Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134620B true NO134620B (xx) | 1976-08-09 |
| NO134620C NO134620C (xx) | 1976-11-17 |
Family
ID=5804786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1300/72A NO134620C (xx) | 1971-04-15 | 1972-04-14 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3769288A (xx) |
| AT (2) | AT315854B (xx) |
| AU (1) | AU467499B2 (xx) |
| BE (1) | BE782157A (xx) |
| CH (2) | CH565178A5 (xx) |
| DE (1) | DE2118261A1 (xx) |
| DK (1) | DK139229C (xx) |
| ES (2) | ES401710A1 (xx) |
| FI (1) | FI54121C (xx) |
| FR (1) | FR2133801B1 (xx) |
| GB (1) | GB1382645A (xx) |
| NL (1) | NL7205028A (xx) |
| NO (1) | NO134620C (xx) |
| SE (1) | SE377690B (xx) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1447426A (en) * | 1974-03-20 | 1976-08-25 | Lepetit Spa | Pyrrolo 3,4-d- pyrimidines and methods for their preparation |
| GB1442483A (en) * | 1974-03-27 | 1976-07-14 | Ici Ltd | Imidazo-1,2-a- pyrimidine derivatives |
| JPS51141896A (en) * | 1975-05-31 | 1976-12-07 | Sankyo Co Ltd | Process for preparing fused ring triazoropyrimidine derivatives |
| CH638215A5 (de) * | 1977-02-04 | 1983-09-15 | Hoffmann La Roche | Oxadiazolopyrimidin-derivate. |
| CH638216A5 (de) * | 1977-02-04 | 1983-09-15 | Hoffmann La Roche | Oxadiazolopyrimidin-deriate. |
| US4153695A (en) * | 1978-03-09 | 1979-05-08 | Eli Lilly And Company | Substituted 2,3-dihydro imidazo[1,2-c]pyrimidines |
| DE2827617A1 (de) * | 1978-06-23 | 1980-01-10 | Boehringer Sohn Ingelheim | Neue imidazo eckige klammer auf 1,2- alpha eckige klammer zu imidazole, deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zu deren herstellung |
| DE3042636A1 (de) * | 1980-11-12 | 1982-06-16 | C.H. Boehringer Sohn, 6507 Ingelheim | Neue 7-(2,6-dibrom-4-methylphenyl)-2,3-dihydro-imidazo(1,2-a)imidazole, deren saeureadditionssalze, diese enhthaltende arzneimittel und verfahren zu deren herstellung |
| DE3124718A1 (de) | 1981-06-24 | 1983-01-13 | Boehringer Ingelheim KG, 6507 Ingelheim | Neue imidazo (1,2-a)pyramidine, deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zu deren herstellung |
| IT1303672B1 (it) * | 1998-07-28 | 2001-02-23 | Nicox Sa | Sali nitrati di farmaci attivi nei disordini ossei |
| US8148490B2 (en) * | 2010-03-10 | 2012-04-03 | Ppg Industries Ohio, Inc. | Method of making a cyclic guanidine from a guanidinium salt and a weak acid and coating compositions containing the same |
| US8563560B2 (en) | 2011-02-25 | 2013-10-22 | Ppg Industries Ohio, Inc. | Preparation of bicyclic guanidine salts in an aqueous media |
| US9068089B2 (en) | 2013-03-15 | 2015-06-30 | Ppg Industries Ohio, Inc. | Phenolic admix for electrodepositable coating composition containing a cyclic guanidine |
| US9688874B2 (en) | 2013-10-25 | 2017-06-27 | Ppg Industries Ohio, Inc. | Method of making a bicyclic guanidine-cured acrylic coating |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2782205A (en) * | 1956-03-29 | 1957-02-19 | Monsanto Canada Ltd | Imidazole derivatives |
-
1971
- 1971-04-15 DE DE19712118261 patent/DE2118261A1/de active Pending
-
1972
- 1972-04-12 US US00243426A patent/US3769288A/en not_active Expired - Lifetime
- 1972-04-13 ES ES401710A patent/ES401710A1/es not_active Expired
- 1972-04-14 AU AU41168/72A patent/AU467499B2/en not_active Expired
- 1972-04-14 FR FR7213330A patent/FR2133801B1/fr not_active Expired
- 1972-04-14 AT AT327672A patent/AT315854B/de not_active IP Right Cessation
- 1972-04-14 BE BE782157A patent/BE782157A/xx unknown
- 1972-04-14 GB GB1740572A patent/GB1382645A/en not_active Expired
- 1972-04-14 CH CH554772A patent/CH565178A5/xx not_active IP Right Cessation
- 1972-04-14 SE SE7204906A patent/SE377690B/xx unknown
- 1972-04-14 NL NL7205028A patent/NL7205028A/xx not_active Application Discontinuation
- 1972-04-14 NO NO1300/72A patent/NO134620C/no unknown
- 1972-04-14 FI FI1071/72A patent/FI54121C/fi active
- 1972-04-14 CH CH454175A patent/CH565179A5/xx not_active IP Right Cessation
- 1972-04-14 AT AT605073A patent/AT316565B/de not_active IP Right Cessation
- 1972-04-14 DK DK183872A patent/DK139229C/da active
-
1973
- 1973-03-13 ES ES412587A patent/ES412587A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI54121C (fi) | 1978-10-10 |
| AT315854B (de) | 1974-06-10 |
| FR2133801B1 (xx) | 1975-10-17 |
| ES412587A1 (es) | 1976-01-16 |
| NL7205028A (xx) | 1972-10-17 |
| BE782157A (fr) | 1972-10-16 |
| DK139229B (da) | 1979-01-15 |
| AT316565B (de) | 1974-07-25 |
| DK139229C (da) | 1979-06-18 |
| CH565178A5 (xx) | 1975-08-15 |
| NO134620C (xx) | 1976-11-17 |
| GB1382645A (en) | 1975-02-05 |
| ES401710A1 (es) | 1975-11-01 |
| FI54121B (fi) | 1978-06-30 |
| SE377690B (xx) | 1975-07-21 |
| AU467499B2 (en) | 1973-10-18 |
| FR2133801A1 (xx) | 1972-12-01 |
| DE2118261A1 (de) | 1972-11-02 |
| CH565179A5 (xx) | 1975-08-15 |
| US3769288A (en) | 1973-10-30 |
| AU4116872A (en) | 1973-10-18 |
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