DE2222210C2 - Katalysatorsystem sowie dessen Verwendung zur Herstellung von Terpolymerkautschuken aus Äthylen, Propylen und nicht-konjugierten polycyclischen Dienen - Google Patents
Katalysatorsystem sowie dessen Verwendung zur Herstellung von Terpolymerkautschuken aus Äthylen, Propylen und nicht-konjugierten polycyclischen DienenInfo
- Publication number
- DE2222210C2 DE2222210C2 DE2222210A DE2222210A DE2222210C2 DE 2222210 C2 DE2222210 C2 DE 2222210C2 DE 2222210 A DE2222210 A DE 2222210A DE 2222210 A DE2222210 A DE 2222210A DE 2222210 C2 DE2222210 C2 DE 2222210C2
- Authority
- DE
- Germany
- Prior art keywords
- propylene
- polypropylene glycol
- ethylene
- production
- catalyst system
- 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
- -1 ethylene, propylene Chemical group 0.000 title claims description 24
- 239000003054 catalyst Substances 0.000 title claims description 19
- 229920001897 terpolymer Polymers 0.000 title claims description 14
- 229920001971 elastomer Polymers 0.000 title claims description 12
- 239000005060 rubber Substances 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 229920001451 polypropylene glycol Polymers 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 238000006116 polymerization reaction Methods 0.000 description 13
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 229910052740 iodine Inorganic materials 0.000 description 9
- 239000011630 iodine Substances 0.000 description 9
- 229920002943 EPDM rubber Polymers 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 150000001993 dienes Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- 229910052720 vanadium Inorganic materials 0.000 description 6
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 6
- OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical group CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 description 5
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- JBIQAPKSNFTACH-UHFFFAOYSA-K vanadium oxytrichloride Chemical compound Cl[V](Cl)(Cl)=O JBIQAPKSNFTACH-UHFFFAOYSA-K 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002879 Lewis base Substances 0.000 description 3
- 125000005234 alkyl aluminium group Chemical group 0.000 description 3
- HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 description 3
- 150000007527 lewis bases Chemical class 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 150000003682 vanadium compounds Chemical class 0.000 description 3
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 2
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 1
- WKWWISMSTOFOGJ-UHFFFAOYSA-N 5-propylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=CCC)CC1C=C2 WKWWISMSTOFOGJ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012967 coordination catalyst Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000003381 stabilizer Substances 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14205871A | 1971-05-10 | 1971-05-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2222210A1 DE2222210A1 (de) | 1972-11-23 |
| DE2222210C2 true DE2222210C2 (de) | 1982-11-18 |
Family
ID=22498402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2222210A Expired DE2222210C2 (de) | 1971-05-10 | 1972-05-05 | Katalysatorsystem sowie dessen Verwendung zur Herstellung von Terpolymerkautschuken aus Äthylen, Propylen und nicht-konjugierten polycyclischen Dienen |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3706718A (OSRAM) |
| JP (1) | JPS5434713B1 (OSRAM) |
| AT (1) | AT329259B (OSRAM) |
| AU (1) | AU4206372A (OSRAM) |
| BE (1) | BE783159A (OSRAM) |
| BR (1) | BR7202881D0 (OSRAM) |
| CA (1) | CA980322A (OSRAM) |
| DE (1) | DE2222210C2 (OSRAM) |
| FR (1) | FR2139322A5 (OSRAM) |
| GB (1) | GB1388947A (OSRAM) |
| IT (1) | IT958830B (OSRAM) |
| NL (1) | NL168236C (OSRAM) |
| ZA (1) | ZA722748B (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3326839A1 (de) * | 1983-07-26 | 1985-02-14 | Bunawerke Hüls GmbH, 4370 Marl | Katalysatorsystem und seine verwendung zur herstellung von epdm-kautschuk |
| EP0321612B1 (en) * | 1987-12-08 | 1992-03-18 | Texaco Development Corporation | Synthesis of vanadium/propylene glycol complexes |
| KR100623106B1 (ko) | 1998-11-02 | 2006-09-13 | 다우 글로벌 테크놀로지스 인크. | 전단시닝 에틸렌／α―올레핀 인터폴리머 및 그의 제조 방법 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3562228A (en) * | 1968-03-25 | 1971-02-09 | Uniroyal Inc | Copolymerization of olefins |
-
1971
- 1971-05-10 US US142058A patent/US3706718A/en not_active Expired - Lifetime
- 1971-09-08 CA CA122,318A patent/CA980322A/en not_active Expired
-
1972
- 1972-04-24 ZA ZA722748A patent/ZA722748B/xx unknown
- 1972-04-26 GB GB1934272A patent/GB1388947A/en not_active Expired
- 1972-05-05 DE DE2222210A patent/DE2222210C2/de not_active Expired
- 1972-05-05 FR FR7216274A patent/FR2139322A5/fr not_active Expired
- 1972-05-08 BE BE783159A patent/BE783159A/xx unknown
- 1972-05-08 AT AT399872A patent/AT329259B/de not_active IP Right Cessation
- 1972-05-09 AU AU42063/72A patent/AU4206372A/en not_active Expired
- 1972-05-09 NL NLAANVRAGE7206276,A patent/NL168236C/xx not_active IP Right Cessation
- 1972-05-09 BR BR2881/72A patent/BR7202881D0/pt unknown
- 1972-05-09 IT IT68459/72A patent/IT958830B/it active
- 1972-05-10 JP JP4559072A patent/JPS5434713B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5434713B1 (OSRAM) | 1979-10-29 |
| NL7206276A (OSRAM) | 1972-11-14 |
| ATA399872A (de) | 1975-07-15 |
| US3706718A (en) | 1972-12-19 |
| NL168236B (nl) | 1981-10-16 |
| IT958830B (it) | 1973-10-30 |
| FR2139322A5 (OSRAM) | 1973-01-05 |
| ZA722748B (en) | 1973-01-31 |
| AT329259B (de) | 1976-05-10 |
| BR7202881D0 (pt) | 1973-06-21 |
| DE2222210A1 (de) | 1972-11-23 |
| GB1388947A (en) | 1975-03-26 |
| AU4206372A (en) | 1973-12-20 |
| NL168236C (nl) | 1982-03-16 |
| BE783159A (fr) | 1972-11-08 |
| CA980322A (en) | 1975-12-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: UNIROYAL CHEMICAL CO., INC., MIDDLEBURY, CONN., US |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: TIEDTKE, H., DIPL.-ING. BUEHLING, G., DIPL.-CHEM. KINNE, R., DIPL.-ING. GRUPE, P., DIPL.-ING. PELLMANN, H., DIPL.-ING. GRAMS, K., DIPL.-ING. STRUIF, B., DIPL.-CHEM. DR.RER.NAT. WINTER, K., DIPL.-ING. ROTH, R., DIPL.-ING., PAT.-ANWAELTE, 8000 MUENCHEN |