CA2338526C - Polymeres d'olefines et de .alpha.-olefines et procedes de polymerisation - Google Patents

Polymeres d'olefines et de .alpha.-olefines et procedes de polymerisation Download PDF

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Publication number: CA2338526C
Authority: CA; Canada
Prior art keywords: hydrocarbyl; substituted; polymers; ethylene; carbon atoms
Prior art date: 1995-01-24
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 - Fee Related

Application number

CA002338526A

Other languages

English (en)

Other versions

CA2338526A1 (fr

Inventor

Jerald Feldman

Christopher Moore Killian

Daniel Joseph Tempel

Stephan James Mclain

Lynda Kaye Johnson

Anju Parthasarathy

Kristina Ann Kreutzer

Samuel David Arthur

Margaret Anne Bennett

Steven Dale Ittel

Edward Bryan Coughlin

Elizabeth Forrester Mccord

Maurice S. Brookhart

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.)

University of North Carolina at Chapel Hill

EIDP Inc

Original Assignee

University of North Carolina at Chapel Hill

EI Du Pont de Nemours and 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.)

1995-01-24

Filing date

1996-01-24

Publication date

2003-12-09

1996-01-24 Application filed by University of North Carolina at Chapel Hill, EI Du Pont de Nemours and Co filed Critical University of North Carolina at Chapel Hill

1996-01-24 Priority claimed from CA002211108A external-priority patent/CA2211108C/fr

1996-08-01 Publication of CA2338526A1 publication Critical patent/CA2338526A1/fr

2003-12-09 Application granted granted Critical

2003-12-09 Publication of CA2338526C publication Critical patent/CA2338526C/fr

2016-01-24 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 146
230000008569 process Effects 0.000 title claims abstract description 89
229920000098 polyolefin Polymers 0.000 title description 32
-1 acyclic olefins Chemical class 0.000 claims abstract description 203
239000005977 Ethylene Substances 0.000 claims abstract description 171
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 170
239000003054 catalyst Substances 0.000 claims abstract description 118
239000003446 ligand Substances 0.000 claims abstract description 40
239000002841 Lewis acid Substances 0.000 claims abstract description 36
230000015572 biosynthetic process Effects 0.000 claims abstract description 19
239000007848 Bronsted acid Substances 0.000 claims abstract description 12
238000006384 oligomerization reaction Methods 0.000 claims abstract 4
125000001183 hydrocarbyl group Chemical group 0.000 claims description 416
150000001875 compounds Chemical class 0.000 claims description 210
229910052739 hydrogen Inorganic materials 0.000 claims description 159
239000001257 hydrogen Substances 0.000 claims description 158
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 137
125000004432 carbon atom Chemical group C* 0.000 claims description 136
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 127
150000001450 anions Chemical class 0.000 claims description 110
229910052799 carbon Inorganic materials 0.000 claims description 98
125000000743 hydrocarbylene group Chemical group 0.000 claims description 92
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 88
125000000217 alkyl group Chemical group 0.000 claims description 82
239000000203 mixture Substances 0.000 claims description 82
229910052757 nitrogen Inorganic materials 0.000 claims description 67
125000004429 atom Chemical group 0.000 claims description 60
NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 claims description 45
230000007935 neutral effect Effects 0.000 claims description 38
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
239000002253 acid Substances 0.000 claims description 28
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
150000007517 lewis acids Chemical class 0.000 claims description 21
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
229910052760 oxygen Inorganic materials 0.000 claims description 19
239000001301 oxygen Substances 0.000 claims description 19
239000002879 Lewis base Substances 0.000 claims description 17
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
150000007527 lewis bases Chemical class 0.000 claims description 17
229910052717 sulfur Inorganic materials 0.000 claims description 17
239000011593 sulfur Substances 0.000 claims description 17
229910052723 transition metal Inorganic materials 0.000 claims description 17
150000003624 transition metals Chemical class 0.000 claims description 17
239000000460 chlorine Substances 0.000 claims description 16
125000002091 cationic group Chemical group 0.000 claims description 14
229910052794 bromium Inorganic materials 0.000 claims description 13
125000002837 carbocyclic group Chemical group 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
229910052740 iodine Inorganic materials 0.000 claims description 7
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
239000011630 iodine Substances 0.000 claims description 3
230000036961 partial effect Effects 0.000 claims description 2
229920000642 polymer Polymers 0.000 abstract description 338
150000001336 alkenes Chemical class 0.000 abstract description 141
239000000178 monomer Substances 0.000 abstract description 130
238000006116 polymerization reaction Methods 0.000 abstract description 125
229910000071 diazene Inorganic materials 0.000 abstract description 37
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239000011347 resin Substances 0.000 abstract description 27
239000000806 elastomer Substances 0.000 abstract description 19
239000000853 adhesive Substances 0.000 abstract description 17
230000001070 adhesive effect Effects 0.000 abstract description 17
150000001735 carboxylic acids Chemical class 0.000 abstract description 13
238000000465 moulding Methods 0.000 abstract description 10
238000003786 synthesis reaction Methods 0.000 abstract description 10
230000000379 polymerizing effect Effects 0.000 abstract description 7
229920001400 block copolymer Polymers 0.000 abstract description 5
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239000003426 co-catalyst Substances 0.000 abstract description 2
238000010550 living polymerization reaction Methods 0.000 abstract description 2
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GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 abstract 1
229960002069 diamorphine Drugs 0.000 abstract 1
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 140
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125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 118
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 107
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 102
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JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 91
229910052786 argon Inorganic materials 0.000 description 90
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 86
150000001721 carbon Chemical group 0.000 description 80
239000000243 solution Substances 0.000 description 72
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 70
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 67
238000005160 1H NMR spectroscopy Methods 0.000 description 63
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
239000004698 Polyethylene Substances 0.000 description 52
JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 52
229920000573 polyethylene Polymers 0.000 description 52
229920001577 copolymer Polymers 0.000 description 51
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 49
150000002148 esters Chemical class 0.000 description 48
239000000047 product Substances 0.000 description 43
229910052751 metal Inorganic materials 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 41
239000002184 metal Substances 0.000 description 41
150000002848 norbornenes Chemical class 0.000 description 40
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239000010408 film Substances 0.000 description 34
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125000003118 aryl group Chemical group 0.000 description 30
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 28
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 28
239000004743 Polypropylene Substances 0.000 description 27
CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 description 27
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 description 25
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125000000524 functional group Chemical group 0.000 description 25
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125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 25
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
238000005481 NMR spectroscopy Methods 0.000 description 24
150000004678 hydrides Chemical class 0.000 description 24
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 23
238000002844 melting Methods 0.000 description 23
230000008018 melting Effects 0.000 description 23
239000003921 oil Substances 0.000 description 23
WXHIJDCHNDBCNY-UHFFFAOYSA-N palladium dihydride Chemical compound [PdH2] WXHIJDCHNDBCNY-UHFFFAOYSA-N 0.000 description 23
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 22
229910052759 nickel Inorganic materials 0.000 description 22
101150073470 Prph gene Proteins 0.000 description 20
238000004458 analytical method Methods 0.000 description 20
RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 20
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 20
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FYJQJMIEZVMYSD-UHFFFAOYSA-N perfluoro-2-butyltetrahydrofuran Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)OC(F)(F)C(F)(F)C1(F)F FYJQJMIEZVMYSD-UHFFFAOYSA-N 0.000 description 19
229920001155 polypropylene Polymers 0.000 description 19
239000003208 petroleum Substances 0.000 description 18
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 17
239000007788 liquid Substances 0.000 description 17
229910052763 palladium Inorganic materials 0.000 description 17
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 17
101150041968 CDC13 gene Proteins 0.000 description 16
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 16
229910002091 carbon monoxide Inorganic materials 0.000 description 16
238000000113 differential scanning calorimetry Methods 0.000 description 16
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
150000001993 dienes Chemical class 0.000 description 15
230000010354 integration Effects 0.000 description 15
239000002685 polymerization catalyst Substances 0.000 description 15
PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 14
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 14
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150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
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239000002002 slurry Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000005476 soldering Methods 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000009987 spinning Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
125000005648 substituted hydrocarbylene group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
238000010557 suspension polymerization reaction Methods 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
PNWOTXLVRDKNJA-UHFFFAOYSA-N tert-butylperoxybenzene Chemical compound CC(C)(C)OOC1=CC=CC=C1 PNWOTXLVRDKNJA-UHFFFAOYSA-N 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
238000002411 thermogravimetry Methods 0.000 description 1
229920002725 thermoplastic elastomer Polymers 0.000 description 1
229920002397 thermoplastic olefin Polymers 0.000 description 1
239000010409 thin film Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
BKHZQJRTFNFCTG-UHFFFAOYSA-N tris(2-methylphenyl) phosphite Chemical compound CC1=CC=CC=C1OP(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C BKHZQJRTFNFCTG-UHFFFAOYSA-N 0.000 description 1
NSBGJRFJIJFMGW-UHFFFAOYSA-N trisodium;stiborate Chemical compound [Na+].[Na+].[Na+].[O-][Sb]([O-])([O-])=O NSBGJRFJIJFMGW-UHFFFAOYSA-N 0.000 description 1
BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
229920006337 unsaturated polyester resin Polymers 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
238000013022 venting Methods 0.000 description 1
FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
239000004034 viscosity adjusting agent Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000002759 woven fabric Substances 0.000 description 1
NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1
229910001928 zirconium oxide Inorganic materials 0.000 description 1

Landscapes

Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA002338526A 1995-01-24 1996-01-24 Polymeres d'olefines et de .alpha.-olefines et procedes de polymerisation Expired - Fee Related CA2338526C (fr)

Applications Claiming Priority (11)

Application Number	Priority Date	Filing Date	Title
US37804495A	1995-01-24	1995-01-24
US08/378,044		1995-01-24
US41528395A	1995-04-03	1995-04-03
US08/415,283		1995-04-03
US47359095A	1995-06-07	1995-06-07
US08/473,590		1995-06-07
US265495P	1995-08-22	1995-08-22
US60/002,654		1995-08-22
US737595P	1995-11-15	1995-11-15
US60/007,375		1995-11-15
CA002211108A CA2211108C (fr)	1995-01-24	1996-01-24	Polymeres d'olefines et de .alpha.-olefines et procedes de polymerisation

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002211108A Division CA2211108C (fr)	1995-01-24	1996-01-24	Polymeres d'olefines et de .alpha.-olefines et procedes de polymerisation

Publications (2)

Publication Number	Publication Date
CA2338526A1 CA2338526A1 (fr)	1996-08-01
CA2338526C true CA2338526C (fr)	2003-12-09

Family

ID=27543509

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CA002338542A Expired - Fee Related CA2338542C (fr)	1995-01-24	1996-01-24	Polymeres d'olefines et de .alpha.-olefines et procedes de polymerisation
CA002338581A Abandoned CA2338581A1 (fr)	1995-01-24	1996-01-24	Polymeres d'olefines et de .alpha.-olefines et procedes de polymerisation
CA002338526A Expired - Fee Related CA2338526C (fr)	1995-01-24	1996-01-24	Polymeres d'olefines et de .alpha.-olefines et procedes de polymerisation

Family Applications Before (2)

Application Number	Title	Priority Date	Filing Date
CA002338542A Expired - Fee Related CA2338542C (fr)	1995-01-24	1996-01-24	Polymeres d'olefines et de .alpha.-olefines et procedes de polymerisation
CA002338581A Abandoned CA2338581A1 (fr)	1995-01-24	1996-01-24	Polymeres d'olefines et de .alpha.-olefines et procedes de polymerisation

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CA (3)	CA2338542C (fr)

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Publication number	Priority date	Publication date	Assignee	Title
CN110452320B (zh) *	2018-05-08	2022-05-10	中国石油天然气股份有限公司	支化聚乙烯的制备方法
US20200270435A1 (en) *	2019-02-27	2020-08-27	Milliken & Company	Method for making heterophasic polymer compositions
CN112250940A (zh) *	2020-10-27	2021-01-22	长春工业大学	一种负载路易斯酸的短切碳纤维增强聚烯烃复合材料及其制备方法
CN114539521B (zh) *	2022-02-25	2023-09-29	中国地质科学院矿产综合利用研究所	一种稀土催化降粘剂及其制备方法和应用

1996
- 1996-01-24 CA CA002338542A patent/CA2338542C/fr not_active Expired - Fee Related
- 1996-01-24 CA CA002338581A patent/CA2338581A1/fr not_active Abandoned
- 1996-01-24 CA CA002338526A patent/CA2338526C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2338526A1 (fr)	1996-08-01
CA2338581A1 (fr)	1996-08-01
CA2338542C (fr)	2004-05-18
CA2338542A1 (fr)	1996-08-01

Legal Events

Date	Code	Title	Description
2001-03-01	EEER	Examination request
2008-01-24	MKLA	Lapsed

Publication	Publication Date	Title
US6218493B1 (en)	2001-04-17	α-olefins and olefin polymers and processes therefor
AU729324B2 (en)	2001-02-01	Alpha-olefins and olefin polymers and processes therefor
US6897272B1 (en)	2005-05-24	α-olefins and olefin polymers and processes therefor
DE69827020T2 (de)	2006-02-02	Olefinenpolymerisation
KR20000067989A (ko)	2000-11-25	올레핀의 중합 방법
CA2338526C (fr)	2003-12-09	Polymeres d'olefines et de .alpha.-olefines et procedes de polymerisation
AU759997B2 (en)	2003-05-01	Alpha-olefins and olefin polymers and processes therefor
AU2003204611B2 (en)	2006-03-02	Alpha-olefins and olefin polymers and processes therefor
CZ2000653A3 (cs)	2000-06-14	Způsob polymerace olefinů
HK1027365B (en)	2005-05-06	Polymerization of olefins