DE2206800C2 - Verfahren zur Polymerisation von konjugierten Dienkohlenwasserstoffen - Google Patents
Verfahren zur Polymerisation von konjugierten DienkohlenwasserstoffenInfo
- Publication number
- DE2206800C2 DE2206800C2 DE2206800A DE2206800A DE2206800C2 DE 2206800 C2 DE2206800 C2 DE 2206800C2 DE 2206800 A DE2206800 A DE 2206800A DE 2206800 A DE2206800 A DE 2206800A DE 2206800 C2 DE2206800 C2 DE 2206800C2
- Authority
- DE
- Germany
- Prior art keywords
- molecular weight
- polymerization
- catalyst
- sodium
- polymers
- 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 27
- 238000006116 polymerization reaction Methods 0.000 title claims description 27
- 229930195733 hydrocarbon Natural products 0.000 title claims description 11
- -1 diene hydrocarbons Chemical class 0.000 title claims description 9
- 239000003054 catalyst Substances 0.000 claims description 35
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 27
- 229920000642 polymer Polymers 0.000 claims description 27
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 20
- 239000011734 sodium Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 238000009826 distribution Methods 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052744 lithium Inorganic materials 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229920001971 elastomer Polymers 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229920002857 polybutadiene Polymers 0.000 claims description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- 150000002739 metals Chemical class 0.000 claims 2
- 239000003607 modifier Substances 0.000 claims 2
- 239000002798 polar solvent Substances 0.000 claims 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 150000001993 dienes Chemical class 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 239000011591 potassium Chemical group 0.000 claims 1
- 230000002787 reinforcement Effects 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- DGTOAFBVEDTEBA-UHFFFAOYSA-N sodium;prop-1-ene Chemical compound [Na+].[CH2-]C=C DGTOAFBVEDTEBA-UHFFFAOYSA-N 0.000 claims 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 claims 1
- 239000012808 vapor phase Substances 0.000 claims 1
- 238000004260 weight control Methods 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- IRDQNLLVRXMERV-UHFFFAOYSA-N CCCC[Na] Chemical compound CCCC[Na] IRDQNLLVRXMERV-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- WRBRIRNGWAUZRF-UHFFFAOYSA-N 2-methyl-2-[(2-methylpropan-2-yl)oxy]propane;sodium Chemical compound [Na].CC(C)(C)OC(C)(C)C WRBRIRNGWAUZRF-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001026509 Kata Species 0.000 description 1
- QIQRVIPQIJRSAD-UHFFFAOYSA-N [Li].CC(C)(C)OC(C)(C)C Chemical compound [Li].CC(C)(C)OC(C)(C)C QIQRVIPQIJRSAD-UHFFFAOYSA-N 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 210000003041 ligament Anatomy 0.000 description 1
- 150000002641 lithium Chemical class 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005303 weighing Methods 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)
- 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 |
|---|---|---|---|
| US11571171A | 1971-02-16 | 1971-02-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2206800A1 DE2206800A1 (de) | 1972-10-05 |
| DE2206800C2 true DE2206800C2 (de) | 1983-03-03 |
Family
ID=22362994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2206800A Expired DE2206800C2 (de) | 1971-02-16 | 1972-02-12 | Verfahren zur Polymerisation von konjugierten Dienkohlenwasserstoffen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3769267A (https=) |
| BR (1) | BR7200839D0 (https=) |
| CA (1) | CA994948A (https=) |
| DE (1) | DE2206800C2 (https=) |
| FR (1) | FR2125934A5 (https=) |
| GB (1) | GB1374212A (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52101287A (en) * | 1976-02-20 | 1977-08-25 | Japan Synthetic Rubber Co Ltd | Preparation of conjugated diene polymers |
| US5260370A (en) * | 1990-09-21 | 1993-11-09 | Bridgestone Corporation | Oil extended ultra high molecular weight elastomers |
| US5272203A (en) * | 1990-09-21 | 1993-12-21 | Bridgestone/Firestone, Inc. | High performance tire treads and tires |
| US5147951A (en) * | 1990-09-21 | 1992-09-15 | Bridgestone/Firestone, Inc. | Method for preparing ultra high molecular weight copolymers of conjugated dienes and aromatic vinyl compounds |
| US5231152A (en) * | 1990-12-18 | 1993-07-27 | Bridgestone Corporation | Continuous process for preparing copolymers of conjugated dienes and aromatic vinyl compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE281966C (https=) * | ||||
| US2999891A (en) * | 1957-09-23 | 1961-09-12 | Exxon Research Engineering Co | Removing alkali metal catalysts from polymers |
-
1971
- 1971-02-16 US US00115711A patent/US3769267A/en not_active Expired - Lifetime
-
1972
- 1972-02-03 CA CA133,927A patent/CA994948A/en not_active Expired
- 1972-02-08 GB GB590472A patent/GB1374212A/en not_active Expired
- 1972-02-11 BR BR839/72A patent/BR7200839D0/pt unknown
- 1972-02-12 DE DE2206800A patent/DE2206800C2/de not_active Expired
- 1972-02-15 FR FR7205073A patent/FR2125934A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA994948A (en) | 1976-08-10 |
| GB1374212A (en) | 1974-11-20 |
| BR7200839D0 (pt) | 1973-05-24 |
| US3769267A (en) | 1973-10-30 |
| FR2125934A5 (https=) | 1972-09-29 |
| DE2206800A1 (de) | 1972-10-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |