CA2338542C - 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: CA2338542C
Authority: CA; Canada
Prior art keywords: hydrocarbyl; independently; carbon atoms; substituted; olefin
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

CA002338542A

Other languages

English (en)

Other versions

CA2338542A1 (fr

Inventor

Anju Parthasarathy

Steven Dale Ittel

Margaret Anne Bennett

Edward Bryan Coughlin

Maurice S. Brookhart

Daniel Joseph Tempel

Kristina Ann Kreutzer

Stephan James Mclain

Jerald Feldman

Lynda Kaye Johnson

Samuel David Arthur

Elizabeth Forrester Mccord

Christopher Moore Killian

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

2004-05-18

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 CA2338542A1 publication Critical patent/CA2338542A1/fr

2004-05-18 Application granted granted Critical

2004-05-18 Publication of CA2338542C publication Critical patent/CA2338542C/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 185
230000008569 process Effects 0.000 title claims abstract description 133
229920000098 polyolefin Polymers 0.000 title description 34
229920000642 polymer Polymers 0.000 claims abstract description 316
-1 acyclic olefins Chemical class 0.000 claims abstract description 166
239000005977 Ethylene Substances 0.000 claims abstract description 144
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 143
239000000178 monomer Substances 0.000 claims abstract description 134
238000006116 polymerization reaction Methods 0.000 claims abstract description 125
239000003054 catalyst Substances 0.000 claims abstract description 99
239000003446 ligand Substances 0.000 claims abstract description 60
239000002841 Lewis acid Substances 0.000 claims abstract description 38
229910000071 diazene Inorganic materials 0.000 claims abstract description 37
230000015572 biosynthetic process Effects 0.000 claims abstract description 17
239000007848 Bronsted acid Substances 0.000 claims abstract description 14
150000003623 transition metal compounds Chemical class 0.000 claims abstract description 3
125000001183 hydrocarbyl group Chemical group 0.000 claims description 518
150000001875 compounds Chemical class 0.000 claims description 222
125000004432 carbon atom Chemical group C* 0.000 claims description 200
229910052739 hydrogen Inorganic materials 0.000 claims description 198
239000001257 hydrogen Substances 0.000 claims description 197
150000001336 alkenes Chemical class 0.000 claims description 177
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 145
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 142
229910052799 carbon Inorganic materials 0.000 claims description 128
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 124
150000001450 anions Chemical class 0.000 claims description 120
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 116
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 116
125000000743 hydrocarbylene group Chemical group 0.000 claims description 102
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 94
125000000217 alkyl group Chemical group 0.000 claims description 93
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 86
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 71
125000004429 atom Chemical group 0.000 claims description 64
NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 claims description 62
239000000203 mixture Substances 0.000 claims description 56
JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 55
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 53
230000007935 neutral effect Effects 0.000 claims description 51
229910052757 nitrogen Inorganic materials 0.000 claims description 50
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 45
150000002848 norbornenes Chemical class 0.000 claims description 45
125000003118 aryl group Chemical group 0.000 claims description 44
229910052723 transition metal Inorganic materials 0.000 claims description 44
150000003624 transition metals Chemical class 0.000 claims description 44
229910052759 nickel Inorganic materials 0.000 claims description 36
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 35
WXHIJDCHNDBCNY-UHFFFAOYSA-N palladium dihydride Chemical group [PdH2] WXHIJDCHNDBCNY-UHFFFAOYSA-N 0.000 claims description 33
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 31
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 31
239000007787 solid Substances 0.000 claims description 31
CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 claims description 30
239000002253 acid Substances 0.000 claims description 28
125000000524 functional group Chemical group 0.000 claims description 28
150000004678 hydrides Chemical class 0.000 claims description 28
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 25
229910052763 palladium Inorganic materials 0.000 claims description 25
150000007517 lewis acids Chemical class 0.000 claims description 23
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
229910052760 oxygen Inorganic materials 0.000 claims description 22
239000001301 oxygen Substances 0.000 claims description 22
229920001519 homopolymer Polymers 0.000 claims description 19
229910052717 sulfur Inorganic materials 0.000 claims description 19
239000002879 Lewis base Substances 0.000 claims description 18
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
150000007527 lewis bases Chemical class 0.000 claims description 18
102200025788 rs179363875 Human genes 0.000 claims description 18
239000011593 sulfur Substances 0.000 claims description 18
125000002091 cationic group Chemical group 0.000 claims description 15
125000002947 alkylene group Chemical group 0.000 claims description 14
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 13
125000002837 carbocyclic group Chemical group 0.000 claims description 13
230000003647 oxidation Effects 0.000 claims description 13
238000007254 oxidation reaction Methods 0.000 claims description 13
RXBMEHOLQJITJI-LEOXJPRUSA-N (4s)-5-amino-4-[[(2s)-2-[[(2s)-2-[[(4-bromophenyl)-hydroxyphosphoryl]methyl]-3-(3-phenyl-1,2-oxazol-5-yl)propanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoic acid Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N)CP(O)(=O)C=1C=CC(Br)=CC=1)C(ON=1)=CC=1C1=CC=CC=C1 RXBMEHOLQJITJI-LEOXJPRUSA-N 0.000 claims description 11
229910052742 iron Inorganic materials 0.000 claims description 11
229910052783 alkali metal Inorganic materials 0.000 claims description 10
229910052761 rare earth metal Inorganic materials 0.000 claims description 10
150000002910 rare earth metals Chemical class 0.000 claims description 10
229910052804 chromium Inorganic materials 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical group 0.000 claims description 9
UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 claims description 9
229910052720 vanadium Inorganic materials 0.000 claims description 9
229910052726 zirconium Inorganic materials 0.000 claims description 9
125000004185 ester group Chemical group 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
229910052706 scandium Inorganic materials 0.000 claims description 8
229930194542 Keto Natural products 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
125000000468 ketone group Chemical group 0.000 claims description 7
229910052719 titanium Inorganic materials 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
239000007800 oxidant agent Substances 0.000 claims description 6
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical group C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 5
125000001033 ether group Chemical group 0.000 claims description 5
150000002815 nickel Chemical group 0.000 claims description 5
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical group [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 4
XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical group [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 3
229910052721 tungsten Inorganic materials 0.000 claims description 3
150000002431 hydrogen Chemical group 0.000 claims 28
101100495913 Arabidopsis thaliana CHR17 gene Proteins 0.000 claims 5
229910017052 cobalt Inorganic materials 0.000 claims 1
239000010941 cobalt Substances 0.000 claims 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
150000002148 esters Chemical class 0.000 abstract description 49
229920005989 resin Polymers 0.000 abstract description 27
239000011347 resin Substances 0.000 abstract description 27
229920001971 elastomer Polymers 0.000 abstract description 22
239000000806 elastomer Substances 0.000 abstract description 19
239000000853 adhesive Substances 0.000 abstract description 16
230000001070 adhesive effect Effects 0.000 abstract description 16
150000001735 carboxylic acids Chemical class 0.000 abstract description 14
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 6
229920001400 block copolymer Polymers 0.000 abstract description 5
150000002816 nickel compounds Chemical class 0.000 abstract description 3
239000003426 co-catalyst Substances 0.000 abstract description 2
238000010550 living polymerization reaction Methods 0.000 abstract description 2
238000006384 oligomerization reaction Methods 0.000 abstract description 2
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 108
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 90
229910052786 argon Inorganic materials 0.000 description 89
150000001721 carbon Chemical group 0.000 description 77
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 73
238000005160 1H NMR spectroscopy Methods 0.000 description 60
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 58
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 54
229920001577 copolymer Polymers 0.000 description 53
239000000243 solution Substances 0.000 description 53
229910052751 metal Inorganic materials 0.000 description 40
239000002184 metal Substances 0.000 description 39
239000000843 powder Substances 0.000 description 39
239000011541 reaction mixture Substances 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 37
239000000047 product Substances 0.000 description 35
239000004698 Polyethylene Substances 0.000 description 33
239000000463 material Substances 0.000 description 33
229920000573 polyethylene Polymers 0.000 description 33
239000002904 solvent Substances 0.000 description 33
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 32
239000010408 film Substances 0.000 description 29
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 27
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 26
101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 description 25
238000005481 NMR spectroscopy Methods 0.000 description 25
101150113676 chr1 gene Proteins 0.000 description 25
YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 24
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
238000002844 melting Methods 0.000 description 20
230000008018 melting Effects 0.000 description 20
239000003921 oil Substances 0.000 description 20
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 20
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 19
239000004743 Polypropylene Substances 0.000 description 19
RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 19
101150073470 Prph gene Proteins 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000003208 petroleum Substances 0.000 description 17
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-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
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 16
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 15
239000000460 chlorine Substances 0.000 description 15
230000010354 integration Effects 0.000 description 15
239000002685 polymerization catalyst Substances 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 14
150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 14
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 14
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 13
150000001993 dienes Chemical class 0.000 description 13
239000007788 liquid Substances 0.000 description 13
238000004519 manufacturing process Methods 0.000 description 13
229910052794 bromium Inorganic materials 0.000 description 12
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239000010410 layer Substances 0.000 description 11
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
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239000004416 thermosoftening plastic Substances 0.000 description 11
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PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 10
101150041968 CDC13 gene Proteins 0.000 description 10
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IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 10
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
238000004458 analytical method Methods 0.000 description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
150000002739 metals Chemical class 0.000 description 10
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
150000003839 salts Chemical class 0.000 description 10
125000001424 substituent group Chemical group 0.000 description 10
239000000725 suspension Substances 0.000 description 10
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
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230000007704 transition Effects 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
229920006337 unsaturated polyester resin Polymers 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
229920002554 vinyl polymer Polymers 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)

CA002338542A 1995-01-24 1996-01-24 Polymeres d'olefines et de .alpha.-olefines et procedes de polymerisation Expired - Fee Related CA2338542C (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
CA2338542A1 CA2338542A1 (fr)	1996-08-01
CA2338542C true CA2338542C (fr)	2004-05-18

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 After (2)

Application Number	Title	Priority Date	Filing Date
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

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CA (3)	CA2338542C (fr)

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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
CA2338526C (fr)	2003-12-09
CA2338581A1 (fr)	1996-08-01
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
AU729324B2 (en)	2001-02-01	Alpha-olefins and olefin polymers and processes therefor
US5886224A (en)	1999-03-23	α-diimines for polymerization catalysts
US6897272B1 (en)	2005-05-24	α-olefins and olefin polymers and processes therefor
US6620896B1 (en)	2003-09-16	Mixed olefin polymerization catalysts, processes employing such catalysts, and polymers obtained therefrom
EP0977785B1 (fr)	2002-12-04	Polymerisation d'olefines
HUP0002912A2 (hu)	2000-12-28	Olefinek polimerizálása
KR20040048375A (ko)	2004-06-09	에틸렌과 다양한 노르보르넨 유도체의 공중합체
CA2338542C (fr)	2004-05-18	Polymeres d'olefines et de .alpha.-olefines et procedes de polymerisation
Khoshsefat et al.	2016	Practical and theoretical study on the α-substituent effect on α-diimine Nickel (II) and Cobalt (II)-based catalysts for polymerization of ethylene
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
CA2283223A1 (fr)	1998-09-17	Catalyseurs de polymerisation d'olefines contenant des metaux de transition des groupes 8-10, ligands bidentes, procedes utilisant de tels catalyseurs et polymeres obtenus a partir de ces procedes
MXPA99008333A (en)	2000-02-02	Olefin polymerization catalysts containing group 8-10 transition metals, bidentale ligantds, processes employing such catalysts and polymers obtained therefrom
MXPA00012012A (en)	2001-09-07	Supported group 8-10 transition metal olefin polymerization catalysts