CA1129841A - Catalyseur et methode de polymerisation - Google Patents

Catalyseur et methode de polymerisation

Info

Publication number: CA1129841A
Authority: CA; Canada
Prior art keywords: catalyst; olefins; organic polymer; titanium; reaction product
Prior art date: 1978-06-05
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

Application number

CA322,358A

Other languages

English (en)

Inventor

Raymond E. Hoff

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Equistar Chemicals LP

Original Assignee

Chemplex Co

Priority date (The priority date 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 date listed.)

1978-06-05

Filing date

1979-02-27

Publication date

1982-08-17

1979-02-27 Application filed by Chemplex Co filed Critical Chemplex Co

1982-08-17 Application granted granted Critical

1982-08-17 Publication of CA1129841A publication Critical patent/CA1129841A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 19
239000002685 polymerization catalyst Substances 0.000 title claims abstract description 7
239000003054 catalyst Substances 0.000 claims abstract description 140
-1 alkyl aluminum halide Chemical class 0.000 claims abstract description 70
239000002245 particle Substances 0.000 claims abstract description 65
239000010936 titanium Substances 0.000 claims abstract description 62
229920000620 organic polymer Polymers 0.000 claims abstract description 49
239000007795 chemical reaction product Substances 0.000 claims abstract description 48
150000001336 alkenes Chemical class 0.000 claims abstract description 44
150000004796 dialkyl magnesium compounds Chemical class 0.000 claims abstract description 33
238000006116 polymerization reaction Methods 0.000 claims abstract description 30
239000002904 solvent Substances 0.000 claims abstract description 30
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 29
150000003609 titanium compounds Chemical class 0.000 claims abstract description 23
239000003426 co-catalyst Substances 0.000 claims abstract description 21
125000005234 alkyl aluminium group Chemical group 0.000 claims abstract description 19
125000000217 alkyl group Chemical group 0.000 claims abstract description 18
238000002156 mixing Methods 0.000 claims abstract description 15
125000005843 halogen group Chemical group 0.000 claims abstract description 13
238000007334 copolymerization reaction Methods 0.000 claims abstract description 9
125000002524 organometallic group Chemical group 0.000 claims abstract description 8
238000001704 evaporation Methods 0.000 claims abstract description 7
230000000379 polymerizing effect Effects 0.000 claims description 58
229910052719 titanium Inorganic materials 0.000 claims description 48
229920000642 polymer Polymers 0.000 claims description 46
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 41
238000004519 manufacturing process Methods 0.000 claims description 31
239000000463 material Substances 0.000 claims description 27
238000002360 preparation method Methods 0.000 claims description 26
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 26
239000000178 monomer Substances 0.000 claims description 14
229920000573 polyethylene Polymers 0.000 claims description 14
239000004698 Polyethylene Substances 0.000 claims description 13
229910052782 aluminium Inorganic materials 0.000 claims description 13
229920000098 polyolefin Polymers 0.000 claims description 12
CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 claims description 11
125000004122 cyclic group Chemical group 0.000 claims description 10
229920000578 graft copolymer Polymers 0.000 claims description 10
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 9
229920001903 high density polyethylene Polymers 0.000 claims description 9
239000011777 magnesium Substances 0.000 claims description 9
229910052749 magnesium Inorganic materials 0.000 claims description 9
235000001055 magnesium Nutrition 0.000 claims description 9
229940091250 magnesium supplement Drugs 0.000 claims description 9
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 8
238000010438 heat treatment Methods 0.000 claims description 8
239000004700 high-density polyethylene Substances 0.000 claims description 8
KJJBSBKRXUVBMX-UHFFFAOYSA-N magnesium;butane Chemical compound [Mg+2].CCC[CH2-].CCC[CH2-] KJJBSBKRXUVBMX-UHFFFAOYSA-N 0.000 claims description 8
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 7
150000008065 acid anhydrides Chemical class 0.000 claims description 6
150000001735 carboxylic acids Chemical class 0.000 claims description 6
YHNWUQFTJNJVNU-UHFFFAOYSA-N magnesium;butane;ethane Chemical compound [Mg+2].[CH2-]C.CCC[CH2-] YHNWUQFTJNJVNU-UHFFFAOYSA-N 0.000 claims description 6
125000003367 polycyclic group Chemical group 0.000 claims description 6
ZKSADANYBSWZAB-UHFFFAOYSA-N CCCCCC[Mg]CCCCCC Chemical compound CCCCCC[Mg]CCCCCC ZKSADANYBSWZAB-UHFFFAOYSA-N 0.000 claims description 5
230000001105 regulatory effect Effects 0.000 claims description 5
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 5
LTEDQKPGOZDGRZ-UHFFFAOYSA-L propan-2-olate;titanium(4+);dichloride Chemical compound Cl[Ti+2]Cl.CC(C)[O-].CC(C)[O-] LTEDQKPGOZDGRZ-UHFFFAOYSA-L 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
238000001035 drying Methods 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 abstract description 7
229910052725 zinc Inorganic materials 0.000 abstract description 2
239000011701 zinc Substances 0.000 abstract description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 34
239000000047 product Substances 0.000 description 28
230000009257 reactivity Effects 0.000 description 24
239000011949 solid catalyst Substances 0.000 description 20
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 16
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 14
239000005977 Ethylene Substances 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
239000001257 hydrogen Substances 0.000 description 10
229910052739 hydrogen Inorganic materials 0.000 description 10
239000000203 mixture Substances 0.000 description 10
229920001577 copolymer Polymers 0.000 description 9
239000000155 melt Substances 0.000 description 9
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
150000008064 anhydrides Chemical class 0.000 description 7
239000012876 carrier material Substances 0.000 description 7
239000000306 component Substances 0.000 description 7
HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 7
KNRCVAANTQNTPT-UHFFFAOYSA-N methyl-5-norbornene-2,3-dicarboxylic anhydride Chemical compound O=C1OC(=O)C2C1C1(C)C=CC2C1 KNRCVAANTQNTPT-UHFFFAOYSA-N 0.000 description 7
239000000843 powder Substances 0.000 description 7
238000010926 purge Methods 0.000 description 7
239000000376 reactant Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
150000004703 alkoxides Chemical class 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000001282 iso-butane Substances 0.000 description 4
235000013847 iso-butane Nutrition 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
150000002681 magnesium compounds Chemical class 0.000 description 3
FEPCMSPFPMPWJK-OLPJDRRASA-N maleopimaric acid Chemical compound C([C@]12C=C([C@H](C[C@@H]11)[C@H]3C(OC(=O)[C@@H]23)=O)C(C)C)C[C@@H]2[C@]1(C)CCC[C@@]2(C)C(O)=O FEPCMSPFPMPWJK-OLPJDRRASA-N 0.000 description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002002 slurry Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
229920001897 terpolymer Polymers 0.000 description 3
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
238000005406 washing Methods 0.000 description 3
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
SDQGRJKYBWFIDP-UHFFFAOYSA-N 3-but-2-enyl-4-methyloxolane-2,5-dione Chemical compound CC=CCC1C(C)C(=O)OC1=O SDQGRJKYBWFIDP-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
238000009826 distribution Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000000227 grinding Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
229920001519 homopolymer Polymers 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000011343 solid material Substances 0.000 description 2
125000003003 spiro group Chemical group 0.000 description 2
ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
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 1
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
QOGMZIQMZUXOKM-UHFFFAOYSA-N 2-(cyclopenten-1-yl)acetic acid Chemical compound OC(=O)CC1=CCCC1 QOGMZIQMZUXOKM-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 description 1
WTQBISBWKRKLIJ-UHFFFAOYSA-N 5-methylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C)CC1C=C2 WTQBISBWKRKLIJ-UHFFFAOYSA-N 0.000 description 1
KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical compound C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 description 1
BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
KKUZFMJIXIFTND-UHFFFAOYSA-N CCCCCC[Mg] Chemical compound CCCCCC[Mg] KKUZFMJIXIFTND-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
101001002470 Homo sapiens Interferon lambda-1 Proteins 0.000 description 1
102100020990 Interferon lambda-1 Human genes 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
229920003347 Microthene® Polymers 0.000 description 1
YFONKFDEZLYQDH-OPQQBVKSSA-N N-[(1R,2S)-2,6-dimethyindan-1-yl]-6-[(1R)-1-fluoroethyl]-1,3,5-triazine-2,4-diamine Chemical compound C[C@@H](F)C1=NC(N)=NC(N[C@H]2C3=CC(C)=CC=C3C[C@@H]2C)=N1 YFONKFDEZLYQDH-OPQQBVKSSA-N 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
241000212342 Sium Species 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
NRIMHVFWRMABGJ-UHFFFAOYSA-N bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid Chemical compound C1C2C(C(=O)O)=C(C(O)=O)C1C=C2 NRIMHVFWRMABGJ-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical group C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
238000012685 gas phase polymerization Methods 0.000 description 1
238000007654 immersion Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
KHARCSTZAGNHOT-UHFFFAOYSA-N naphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 KHARCSTZAGNHOT-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000010525 oxidative degradation reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229920005638 polyethylene monopolymer Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000001175 rotational moulding Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
230000005476 size effect Effects 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
239000004711 α-olefin 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
- C08F10/00—Homopolymers and 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)
Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Adhesives Or Adhesive Processes (AREA)

CA322,358A 1978-06-05 1979-02-27 Catalyseur et methode de polymerisation Expired CA1129841A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US91287478A	1978-06-05	1978-06-05
US912,874		1992-07-13

Publications (1)

Publication Number	Publication Date
CA1129841A true CA1129841A (fr)	1982-08-17

Family

ID=25432599

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA322,358A Expired CA1129841A (fr)	1978-06-05	1979-02-27	Catalyseur et methode de polymerisation

Country Status (9)

Country	Link
JP (1)	JPS588697B2 (fr)
BE (1)	BE876583A (fr)
CA (1)	CA1129841A (fr)
DE (1)	DE2922068A1 (fr)
FI (1)	FI66189C (fr)
FR (1)	FR2428055A1 (fr)
GB (1)	GB2022102B (fr)
NL (1)	NL175422C (fr)
NO (1)	NO155199C (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0284405A (ja) *	1988-09-20	1990-03-26	Mitsubishi Petrochem Co Ltd	エチレン重合体の製造法
US6063725A (en) *	1995-11-07	2000-05-16	Mitsui Chemicals, Inc.	Olefin polymerization catalyst system

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL165180B (nl) *	1971-03-11	1980-10-15	Stamicarbon	Werkwijze voor het polymeriseren van etheen.
US3873643A (en) *	1972-12-18	1975-03-25	Chemplex Co	Graft copolymers of polyolefins and cyclic acid and acid anhydride monomers
DD126655A1 (fr) *	1975-10-23	1977-08-03

1979
- 1979-02-27 CA CA322,358A patent/CA1129841A/fr not_active Expired
- 1979-03-28 NO NO791025A patent/NO155199C/no unknown
- 1979-04-02 GB GB7911424A patent/GB2022102B/en not_active Expired
- 1979-04-06 FI FI791141A patent/FI66189C/fi not_active IP Right Cessation
- 1979-05-16 JP JP54059211A patent/JPS588697B2/ja not_active Expired
- 1979-05-28 BE BE0/195424A patent/BE876583A/fr unknown
- 1979-05-29 NL NLAANVRAGE7904197,A patent/NL175422C/xx not_active IP Right Cessation
- 1979-05-30 DE DE19792922068 patent/DE2922068A1/de not_active Withdrawn
- 1979-06-01 FR FR7914102A patent/FR2428055A1/fr active Granted

Also Published As

Publication number	Publication date
GB2022102A (en)	1979-12-12
DE2922068A1 (de)	1979-12-06
FR2428055A1 (fr)	1980-01-04
FI66189C (fi)	1984-09-10
GB2022102B (en)	1982-08-11
FI791141A7 (fi)	1979-12-06
NL175422C (nl)	1984-11-01
FR2428055B1 (fr)	1985-05-24
JPS54159490A (en)	1979-12-17
NO791025L (no)	1979-12-06
JPS588697B2 (ja)	1983-02-17
NO155199B (no)	1986-11-17
BE876583A (fr)	1979-09-17
FI66189B (fi)	1984-05-31
NL7904197A (nl)	1979-12-07
NO155199C (no)	1987-02-25

Legal Events

Date	Code	Title	Description
1999-08-17	MKEX	Expiry

Publication	Publication Date	Title
FI110104B (fi)	2002-11-29	Menetelmä eteenin polymeroimiseksi
KR890002933B1 (ko)	1989-08-12	유동상에서의 저밀도 저강도 에틸렌 공중합체 제조방법
CA1332012C (fr)	1994-09-13	Methode de fabrication de copolymeres de propylene
US5409875A (en)	1995-04-25	Polymer-supported catalyst for polymerization and copolymerization of olefins
HU218966B (hu)	2001-01-29	Eljárás katalizátorhordozók előállítására és hordozós poliolefin katalizátorok, valamint ezek alkalmazása poliolefinek előállítására
EP0120501B1 (fr)	1989-05-31	Polymérisation de l'éthylène utilisant un catalyseur au vanadium supporté
JP3434861B2 (ja)	2003-08-11	チーグラー・ナッタ型触媒の製造方法
CA2103632A1 (fr)	1994-02-11	Procede d'obtention de polymeres d'ethylene a teneur reduite en hexane extractible
JPH04226509A (ja)	1992-08-17	広い或は二モードのｍｗ分布を有するポリエチレンを製造するための新規な共含浸バナジウム−ジルコニウム触媒
US4268418A (en)	1981-05-19	Polymerization catalyst
CA2060053A1 (fr)	1992-07-29	Procede d'obtention de polymeres d'ethylene
EP0435557A2 (fr)	1991-07-03	Composition catalytiques pour polymérisation d'oléfines activée pour le chlorure de diméthylaluminium
JPS6060113A (ja)	1985-04-06	エチレン高温重合用の担持ポリオレフイン触媒
EP0285137B1 (fr)	1993-03-17	Catalyseur de polymérisation d'éthylène
CA1129841A (fr)	1982-08-17	Catalyseur et methode de polymerisation
US4404343A (en)	1983-09-13	Method of polymerizing 1-olefins
WO1997045454A2 (fr)	1997-12-04	Terpolymerisation
EP0358264A2 (fr)	1990-03-14	Composant de catalyseur et catalyseur pour la production de polyoléfines à très haut poids moléculaire
CA1216398A (fr)	1987-01-06	Poly er sa ion de l'ethylene
US3819599A (en)	1974-06-25	Catalyst and process for the polymerization of ethylene and terminal olefins
US4208304A (en)	1980-06-17	Catalyst system for producing ethylene polymers
KR950009729B1 (ko)	1995-08-26	고활성 바나듐-기본 촉매
US5177042A (en)	1993-01-05	High activity vanadium-based catalyst
FI96769C (fi)	1996-08-26	Etyleenin polymerointimenetelmä, jonka avulla on mahdollista saada molekyylimassajakaumaltaan laaja polymeeri. Katalyyttisen komponentin käsittelymenetelmä
KR100251599B1 (ko)	2000-04-15	구상 촉매 성분의 제조방법