CA1112799A - Method for the preparation of copolymers of ethylene and polyenes with high yields - Google Patents
Method for the preparation of copolymers of ethylene and polyenes with high yieldsInfo
- Publication number
- CA1112799A CA1112799A CA282,224A CA282224A CA1112799A CA 1112799 A CA1112799 A CA 1112799A CA 282224 A CA282224 A CA 282224A CA 1112799 A CA1112799 A CA 1112799A
- Authority
- CA
- Canada
- Prior art keywords
- ethylene
- interpolymers
- unsaturation
- units
- carrying
- 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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 239000005977 Ethylene Substances 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 229920001577 copolymer Polymers 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 12
- 150000004291 polyenes Chemical class 0.000 title abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 10
- 150000003682 vanadium compounds Chemical class 0.000 claims abstract description 10
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 4
- 229920000642 polymer Polymers 0.000 claims description 23
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- -1 polyene hydrocarbons Chemical class 0.000 claims description 10
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 claims description 9
- 238000002844 melting Methods 0.000 claims description 9
- 230000008018 melting Effects 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- NSWUXAUIAZVROT-UHFFFAOYSA-N 1-(2-cyclopenta-1,3-dien-1-ylpropan-2-yl)cyclopenta-1,3-diene Chemical compound C=1C=CCC=1C(C)(C)C1=CC=CC1 NSWUXAUIAZVROT-UHFFFAOYSA-N 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 238000004132 cross linking Methods 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 238000009826 distribution Methods 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229920002521 macromolecule Polymers 0.000 claims description 2
- 150000003254 radicals Chemical group 0.000 claims description 2
- 239000012066 reaction slurry Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- OJOWICOBYCXEKR-UHFFFAOYSA-N 5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=CC)CC1C=C2 OJOWICOBYCXEKR-UHFFFAOYSA-N 0.000 claims 1
- SQAKRHGQZJZSRW-UHFFFAOYSA-N C12(C=CC(CC1)C2)C2=C(CCC=C2)C(C)(C)C.C Chemical compound C12(C=CC(CC1)C2)C2=C(CCC=C2)C(C)(C)C.C SQAKRHGQZJZSRW-UHFFFAOYSA-N 0.000 claims 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 abstract description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 2
- 150000004820 halides Chemical class 0.000 abstract description 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 14
- 229940045605 vanadium Drugs 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000013329 compounding Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 4
- 101000798109 Homo sapiens Melanotransferrin Proteins 0.000 description 3
- 102100032239 Melanotransferrin Human genes 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- JESYUGLAAYESAZ-UHFFFAOYSA-N 2,3-dimethyl-1-penta-1,3-dienylbicyclo[2.2.1]hept-2-ene Chemical compound CC1=C(C2(CCC1C2)C=CC=CC)C JESYUGLAAYESAZ-UHFFFAOYSA-N 0.000 description 2
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 125000005287 vanadyl group Chemical group 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- ZWVMLYRJXORSEP-LURJTMIESA-N (2s)-hexane-1,2,6-triol Chemical compound OCCCC[C@H](O)CO ZWVMLYRJXORSEP-LURJTMIESA-N 0.000 description 1
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
- OTTZHAVKAVGASB-HYXAFXHYSA-N 2-Heptene Chemical compound CCCC\C=C/C OTTZHAVKAVGASB-HYXAFXHYSA-N 0.000 description 1
- OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- 101100108738 Arabidopsis thaliana ML2 gene Proteins 0.000 description 1
- 101100451301 Caenorhabditis elegans mls-2 gene Proteins 0.000 description 1
- HJEINPVZRDJRBY-UHFFFAOYSA-N Disul Chemical compound OS(=O)(=O)OCCOC1=CC=C(Cl)C=C1Cl HJEINPVZRDJRBY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 101100512787 Schizosaccharomyces pombe (strain 972 / ATCC 24843) mei2 gene Proteins 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 241000765309 Vanadis Species 0.000 description 1
- 229910021552 Vanadium(IV) chloride Inorganic materials 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 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
- 230000002311 subsequent effect Effects 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical compound Cl[V](Cl)(Cl)Cl JTJFQBNJBPPZRI-UHFFFAOYSA-J 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000008096 xylene 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
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/14—Organic medium
-
- 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
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25379/76A IT1064663B (it) | 1976-07-16 | 1976-07-16 | Procedimento per la preparazione in alta resa di copolimeri dell etilene con polieni |
| IT25379A/76 | 1976-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1112799A true CA1112799A (en) | 1981-11-17 |
Family
ID=11216523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA282,224A Expired CA1112799A (en) | 1976-07-16 | 1977-07-07 | Method for the preparation of copolymers of ethylene and polyenes with high yields |
Country Status (20)
-
1976
- 1976-07-16 IT IT25379/76A patent/IT1064663B/it active
-
1977
- 1977-07-06 IL IL52475A patent/IL52475A/xx unknown
- 1977-07-07 GB GB35803/79A patent/GB1589097A/en not_active Expired
- 1977-07-07 GB GB28622/77A patent/GB1589095A/en not_active Expired
- 1977-07-07 GB GB35802/79A patent/GB1589096A/en not_active Expired
- 1977-07-07 AU AU26852/77A patent/AU512515B2/en not_active Expired
- 1977-07-07 CA CA282,224A patent/CA1112799A/en not_active Expired
- 1977-07-13 DD DD7700200041A patent/DD130483A5/xx unknown
- 1977-07-13 NL NL7707832A patent/NL7707832A/xx not_active Application Discontinuation
- 1977-07-13 CS CS774674A patent/CS199508B2/cs unknown
- 1977-07-13 FR FR7721715A patent/FR2358429A1/fr active Granted
- 1977-07-14 YU YU01749/77A patent/YU174977A/xx unknown
- 1977-07-14 CH CH873977A patent/CH628909A5/it not_active IP Right Cessation
- 1977-07-14 JP JP8363777A patent/JPS5311983A/ja active Pending
- 1977-07-14 NO NO772510A patent/NO147214C/no unknown
- 1977-07-14 LU LU77761A patent/LU77761A1/xx unknown
- 1977-07-15 SE SE7708247A patent/SE7708247L/xx not_active Application Discontinuation
- 1977-07-15 ZA ZA00774264A patent/ZA774264B/xx unknown
- 1977-07-15 DK DK323377A patent/DK323377A/da not_active Application Discontinuation
- 1977-07-15 DE DE19772732110 patent/DE2732110A1/de not_active Withdrawn
- 1977-07-15 HU HU77SA3047A patent/HU178728B/hu unknown
- 1977-07-15 BE BE179391A patent/BE856867A/xx not_active IP Right Cessation
-
1982
- 1982-07-05 YU YU01458/82A patent/YU145882A/xx unknown
- 1982-07-05 YU YU01457/82A patent/YU145782A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LU77761A1 (enrdf_load_stackoverflow) | 1977-10-17 |
| FR2358429A1 (fr) | 1978-02-10 |
| AU2685277A (en) | 1979-01-11 |
| NO772510L (no) | 1978-01-17 |
| JPS5311983A (en) | 1978-02-02 |
| GB1589095A (en) | 1981-05-07 |
| HU178728B (en) | 1982-06-28 |
| IT1064663B (it) | 1985-02-25 |
| YU145882A (en) | 1983-10-31 |
| CH628909A5 (en) | 1982-03-31 |
| CS199508B2 (en) | 1980-07-31 |
| NL7707832A (nl) | 1978-01-18 |
| NO147214B (no) | 1982-11-15 |
| YU145782A (en) | 1983-10-31 |
| BE856867A (fr) | 1978-01-16 |
| YU174977A (en) | 1982-10-31 |
| ZA774264B (en) | 1978-06-28 |
| NO147214C (no) | 1983-02-23 |
| FR2358429B1 (enrdf_load_stackoverflow) | 1981-05-22 |
| DE2732110A1 (de) | 1978-01-19 |
| DK323377A (da) | 1978-01-17 |
| DD130483A5 (de) | 1978-04-05 |
| IL52475A0 (en) | 1977-10-31 |
| AU512515B2 (en) | 1980-10-16 |
| GB1589096A (en) | 1981-05-07 |
| GB1589097A (en) | 1981-05-07 |
| IL52475A (en) | 1981-10-30 |
| SE7708247L (sv) | 1978-01-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |