CA1046196A - Process for the preparation of ethylene-propylene-butadiene terpolymers with high yield - Google Patents
Process for the preparation of ethylene-propylene-butadiene terpolymers with high yieldInfo
- Publication number
- CA1046196A CA1046196A CA231,789A CA231789A CA1046196A CA 1046196 A CA1046196 A CA 1046196A CA 231789 A CA231789 A CA 231789A CA 1046196 A CA1046196 A CA 1046196A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- compounds
- vanadium
- molar ratio
- varies
- 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-butadiene Chemical class 0.000 title claims abstract description 11
- 229920001897 terpolymer Polymers 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims abstract 3
- 238000000034 method Methods 0.000 title claims description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 14
- 150000003682 vanadium compounds Chemical class 0.000 claims abstract description 5
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 4
- 229940077746 antacid containing aluminium compound Drugs 0.000 claims abstract 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 15
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 13
- 239000004411 aluminium Substances 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- 239000003849 aromatic solvent Substances 0.000 claims description 4
- 125000005287 vanadyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- JBZRLVKMCLOFLG-UHFFFAOYSA-N O=S=Cl Chemical compound O=S=Cl JBZRLVKMCLOFLG-UHFFFAOYSA-N 0.000 claims 1
- 150000001399 aluminium compounds Chemical class 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 8
- 239000003054 catalyst Substances 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 38
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- VHFUHRXYRYWELT-UHFFFAOYSA-N methyl 2,2,2-trichloroacetate Chemical compound COC(=O)C(Cl)(Cl)Cl VHFUHRXYRYWELT-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001676573 Minium Species 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 229910021551 Vanadium(III) chloride Inorganic materials 0.000 description 1
- 229910021552 Vanadium(IV) chloride Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- YXIWHUQXZSMYRE-UHFFFAOYSA-N benzothiazolyl mercaptan Natural products C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- VGHOWOWLIXPTOA-UHFFFAOYSA-N cyclohexane;toluene Chemical compound C1CCCCC1.CC1=CC=CC=C1 VGHOWOWLIXPTOA-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- PALZAXLZULBBHA-UHFFFAOYSA-N dimethylazanide;vanadium(4+) Chemical compound [V+4].C[N-]C.C[N-]C.C[N-]C.C[N-]C PALZAXLZULBBHA-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000028016 temperature homeostasis Effects 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical compound Cl[V](Cl)(Cl)Cl JTJFQBNJBPPZRI-UHFFFAOYSA-J 0.000 description 1
- HQYCOEXWFMFWLR-UHFFFAOYSA-K vanadium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[V+3] HQYCOEXWFMFWLR-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/02—Ethene
-
- 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
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/06—Propene
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25935/74A IT1017871B (it) | 1974-08-02 | 1974-08-02 | Procedimento per la preparazione in alta resa di terpolimeri etile ne propilene butadiene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1046196A true CA1046196A (en) | 1979-01-09 |
Family
ID=11218184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA231,789A Expired CA1046196A (en) | 1974-08-02 | 1975-07-18 | Process for the preparation of ethylene-propylene-butadiene terpolymers with high yield |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5137985A (is") |
| AU (1) | AU8309875A (is") |
| BE (1) | BE832054A (is") |
| CA (1) | CA1046196A (is") |
| CH (1) | CH606149A5 (is") |
| DD (1) | DD119250A5 (is") |
| DE (1) | DE2534496C2 (is") |
| DK (1) | DK351675A (is") |
| FR (1) | FR2280657A1 (is") |
| GB (3) | GB1519477A (is") |
| IL (1) | IL47733A0 (is") |
| IT (1) | IT1017871B (is") |
| LU (1) | LU73124A1 (is") |
| NL (1) | NL7509171A (is") |
| NO (1) | NO752705L (is") |
| SE (1) | SE7508742L (is") |
| ZA (1) | ZA754583B (is") |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52156195A (en) * | 1976-06-22 | 1977-12-26 | Mitsubishi Chem Ind Ltd | Production of solid catalyst and olefin polymers |
| JPS52156795A (en) * | 1976-06-23 | 1977-12-27 | Mitsubishi Chem Ind Ltd | Production of solid catalyst and olefin polymers |
| IT1197320B (it) * | 1986-10-02 | 1988-11-30 | Ausimont Spa | Catalizzatori per la preparazione di copolimeri olefinici elastomerici,saturi ed insaturi,e vopolimeri con essi ottenuti |
| US5219961A (en) * | 1987-07-30 | 1993-06-15 | Ausimont S.P.A. | Catalysts for preparing saturated elastomeric olefinic copolymers and terpolymers |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1370358A (fr) * | 1962-09-28 | 1964-08-21 | Hoechst Ag | Procédé de préparation de copolymères d'alpha-oléfines et de dioléfines à l'aide de catalyseurs mixtes organo-métalliques modifiés |
| FR1471472A (fr) * | 1965-03-25 | 1967-03-03 | Huels Chemische Werke Ag | Procédé de préparation de copolymères de poids moléculaire élevé à partir de 1-oléfines seules ou en mélange avec des polyoléfines |
| FR1477275A (fr) * | 1965-05-08 | 1967-04-14 | Huels Chemische Werke Ag | Procédé pour préparer des copolymères amorphes de poids moléculaire élevé, à partir de l-oléfines seules ou en métlange avec des poly-oléfines |
| SE358644B (is") * | 1968-12-31 | 1973-08-06 | Montedison Spa | |
| US3682870A (en) * | 1969-01-15 | 1972-08-08 | Goodrich Co B F | Process for the preparation of linear,high molecular weight,sulphur vulcanizable copolymer of ethylene,propylene and 1,3-butadiene and catalyst systems used therein |
| US3756995A (en) * | 1970-04-10 | 1973-09-04 | Japan Synthetic Rubber Co Ltd | Svanadium compound trialkyl aluminum haloorganic acid catalytic proces |
-
1974
- 1974-08-02 IT IT25935/74A patent/IT1017871B/it active
-
1975
- 1975-07-16 ZA ZA00754583A patent/ZA754583B/xx unknown
- 1975-07-16 AU AU83098/75A patent/AU8309875A/en not_active Expired
- 1975-07-17 GB GB3275/78A patent/GB1519477A/en not_active Expired
- 1975-07-17 GB GB30116/75A patent/GB1519472A/en not_active Expired
- 1975-07-17 GB GB3274/78A patent/GB1519476A/en not_active Expired
- 1975-07-18 CA CA231,789A patent/CA1046196A/en not_active Expired
- 1975-07-18 IL IL47733A patent/IL47733A0/xx unknown
- 1975-07-29 FR FR7523698A patent/FR2280657A1/fr active Granted
- 1975-07-31 DD DD187602A patent/DD119250A5/xx unknown
- 1975-07-31 NL NL7509171A patent/NL7509171A/xx not_active Application Discontinuation
- 1975-07-31 LU LU73124A patent/LU73124A1/xx unknown
- 1975-07-31 CH CH1007675A patent/CH606149A5/xx not_active IP Right Cessation
- 1975-08-01 DE DE2534496A patent/DE2534496C2/de not_active Expired
- 1975-08-01 SE SE7508742A patent/SE7508742L/xx unknown
- 1975-08-01 NO NO752705A patent/NO752705L/no unknown
- 1975-08-01 BE BE158881A patent/BE832054A/xx unknown
- 1975-08-01 JP JP50093240A patent/JPS5137985A/ja active Pending
- 1975-08-01 DK DK351675A patent/DK351675A/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD119250A5 (is") | 1976-04-12 |
| DE2534496C2 (de) | 1982-01-21 |
| JPS5137985A (is") | 1976-03-30 |
| GB1519476A (en) | 1978-07-26 |
| GB1519472A (en) | 1978-07-26 |
| CH606149A5 (is") | 1978-10-31 |
| NO752705L (is") | 1976-02-03 |
| IT1017871B (it) | 1977-08-10 |
| AU8309875A (en) | 1977-01-20 |
| FR2280657B1 (is") | 1979-07-13 |
| NL7509171A (nl) | 1976-02-04 |
| BE832054A (fr) | 1976-02-02 |
| FR2280657A1 (fr) | 1976-02-27 |
| IL47733A0 (en) | 1975-10-15 |
| LU73124A1 (is") | 1976-03-02 |
| ZA754583B (en) | 1976-07-28 |
| SE7508742L (sv) | 1976-02-03 |
| DE2534496A1 (de) | 1976-02-12 |
| GB1519477A (en) | 1978-07-26 |
| DK351675A (da) | 1976-02-03 |
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