CA2322496A1 - Copolymeres d'ethylene a repartition etroite de la composition et a temperatures de fusion elevees, et procedes de production desdits copolymeres - Google Patents
Copolymeres d'ethylene a repartition etroite de la composition et a temperatures de fusion elevees, et procedes de production desdits copolymeres Download PDFInfo
- Publication number
- CA2322496A1 CA2322496A1 CA002322496A CA2322496A CA2322496A1 CA 2322496 A1 CA2322496 A1 CA 2322496A1 CA 002322496 A CA002322496 A CA 002322496A CA 2322496 A CA2322496 A CA 2322496A CA 2322496 A1 CA2322496 A1 CA 2322496A1
- Authority
- CA
- Canada
- Prior art keywords
- copolymer
- comonomer
- ethylene
- bis
- copolymers
- 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.)
- Abandoned
Links
- 238000002844 melting Methods 0.000 title claims abstract description 102
- 230000008018 melting Effects 0.000 title claims abstract description 100
- 239000000203 mixture Substances 0.000 title claims abstract description 79
- 238000009826 distribution Methods 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims description 62
- 238000004519 manufacturing process Methods 0.000 title description 8
- 229920001038 ethylene copolymer Polymers 0.000 title description 6
- 229920001577 copolymer Polymers 0.000 claims abstract description 203
- 239000005977 Ethylene Substances 0.000 claims abstract description 64
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 63
- 239000003054 catalyst Substances 0.000 claims abstract description 56
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 42
- 239000000178 monomer Substances 0.000 claims abstract description 40
- 238000000113 differential scanning calorimetry Methods 0.000 claims abstract description 23
- 229920005604 random copolymer Polymers 0.000 claims abstract description 17
- 230000007704 transition Effects 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 229920000642 polymer Polymers 0.000 claims description 67
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000003446 ligand Substances 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 25
- -1 triflouromethyl Chemical group 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 229920001971 elastomer Polymers 0.000 claims description 18
- 239000000806 elastomer Substances 0.000 claims description 18
- 150000001336 alkenes Chemical class 0.000 claims description 15
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052735 hafnium Inorganic materials 0.000 claims description 9
- 239000004711 α-olefin Substances 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- VXNZUUAINFGPBY-UHFFFAOYSA-N ethyl ethylene Natural products CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 8
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 7
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 6
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 5
- 229910052726 zirconium Inorganic materials 0.000 claims description 5
- 229920000034 Plastomer Polymers 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000008188 pellet Substances 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 87
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 83
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 66
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 59
- 239000000243 solution Substances 0.000 description 57
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 39
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 32
- 239000002904 solvent Substances 0.000 description 31
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 30
- 239000007787 solid Substances 0.000 description 27
- 238000005481 NMR spectroscopy Methods 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 239000000463 material Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- 238000007334 copolymerization reaction Methods 0.000 description 20
- 238000005194 fractionation Methods 0.000 description 20
- 230000008569 process Effects 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- KUNZSLJMPCDOGI-UHFFFAOYSA-L [Cl-].[Cl-].[Hf+2] Chemical compound [Cl-].[Cl-].[Hf+2] KUNZSLJMPCDOGI-UHFFFAOYSA-L 0.000 description 15
- 229960004132 diethyl ether Drugs 0.000 description 15
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 14
- 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 14
- 239000013078 crystal Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- 239000012968 metallocene catalyst Substances 0.000 description 12
- 230000035882 stress Effects 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 101150041968 CDC13 gene Proteins 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 230000001965 increasing effect Effects 0.000 description 10
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 10
- 238000011084 recovery Methods 0.000 description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000012530 fluid Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 8
- 229920000098 polyolefin Polymers 0.000 description 8
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000001294 propane Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 230000002902 bimodal effect Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000009257 reactivity Effects 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 5
- 230000004927 fusion Effects 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 238000003780 insertion Methods 0.000 description 5
- 230000037431 insertion Effects 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 230000000717 retained effect Effects 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 229920001169 thermoplastic Polymers 0.000 description 5
- 239000004416 thermosoftening plastic Substances 0.000 description 5
- 229910052723 transition metal Inorganic materials 0.000 description 5
- 150000003624 transition metals Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000004009 13C{1H}-NMR spectroscopy Methods 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- JEKOISATHYKFFC-UHFFFAOYSA-L [Cl-].[Cl-].C=1C=CC=CC=1C1=CC2=CC=CC=C2C1[Zr+2]C(C1=CC=CC=C1C=1)C=1C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C=1C=CC=CC=1C1=CC2=CC=CC=C2C1[Zr+2]C(C1=CC=CC=C1C=1)C=1C1=CC=CC=C1 JEKOISATHYKFFC-UHFFFAOYSA-L 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 229920000092 linear low density polyethylene Polymers 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- DWDOUGVYTPUAHL-UHFFFAOYSA-L [Cl-].[Cl-].C=1C=CC=CC=1C1=CC2=CC=CC=C2C1[Hf+2]C(C1=CC=CC=C1C=1)C=1C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C=1C=CC=CC=1C1=CC2=CC=CC=C2C1[Hf+2]C(C1=CC=CC=C1C=1)C=1C1=CC=CC=C1 DWDOUGVYTPUAHL-UHFFFAOYSA-L 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000005103 alkyl silyl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000001186 cumulative effect Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229920006124 polyolefin elastomer Polymers 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 229920002397 thermoplastic olefin Polymers 0.000 description 3
- 238000004073 vulcanization Methods 0.000 description 3
- PFXYQVJESZAMSV-UHFFFAOYSA-K zirconium(iii) chloride Chemical compound Cl[Zr](Cl)Cl PFXYQVJESZAMSV-UHFFFAOYSA-K 0.000 description 3
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- BSBXLZYWGGAVHD-UHFFFAOYSA-N 2-phenyl-1h-indene Chemical compound C=1C2=CC=CC=C2CC=1C1=CC=CC=C1 BSBXLZYWGGAVHD-UHFFFAOYSA-N 0.000 description 2
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 244000248349 Citrus limon Species 0.000 description 2
- 235000005979 Citrus limon Nutrition 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- GJPSGHWMPGQYCH-UHFFFAOYSA-L [Cl-].[Cl-].CC(C)(C)C1=CC(C(C)(C)C)=CC(C=2C(C3=CC=CC=C3C=2)[Hf+2]C2C3=CC=CC=C3C=C2C=2C=C(C=C(C=2)C(C)(C)C)C(C)(C)C)=C1 Chemical compound [Cl-].[Cl-].CC(C)(C)C1=CC(C(C)(C)C)=CC(C=2C(C3=CC=CC=C3C=2)[Hf+2]C2C3=CC=CC=C3C=C2C=2C=C(C=C(C=2)C(C)(C)C)C(C)(C)C)=C1 GJPSGHWMPGQYCH-UHFFFAOYSA-L 0.000 description 2
- NIBLTNOUIXMQIQ-UHFFFAOYSA-L [Cl-].[Cl-].CC1C(=C([Zr++]C2C(=Cc3ccccc23)c2ccccc2)c2ccccc12)c1cc(cc(c1)C(F)(F)F)C(F)(F)F Chemical compound [Cl-].[Cl-].CC1C(=C([Zr++]C2C(=Cc3ccccc23)c2ccccc2)c2ccccc12)c1cc(cc(c1)C(F)(F)F)C(F)(F)F NIBLTNOUIXMQIQ-UHFFFAOYSA-L 0.000 description 2
- XYTZBJVSKSHMKK-UHFFFAOYSA-L [Cl-].[Cl-].C[Si](C)(C)C1=CC([Si](C)(C)C)=CC(C=2C(C3=CC=CC=C3C=2)[Hf+2]C2C3=CC=CC=C3C=C2C=2C=C(C=C(C=2)[Si](C)(C)C)[Si](C)(C)C)=C1 Chemical compound [Cl-].[Cl-].C[Si](C)(C)C1=CC([Si](C)(C)C)=CC(C=2C(C3=CC=CC=C3C=2)[Hf+2]C2C3=CC=CC=C3C=C2C=2C=C(C=C(C=2)[Si](C)(C)C)[Si](C)(C)C)=C1 XYTZBJVSKSHMKK-UHFFFAOYSA-L 0.000 description 2
- ZCCHLLXYICOYJZ-UHFFFAOYSA-K [Cl-].[Cl-].[Cl-].C=1C2=CC=CC=C2C([Zr+3])C=1C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].[Cl-].C=1C2=CC=CC=C2C([Zr+3])C=1C1=CC=CC=C1 ZCCHLLXYICOYJZ-UHFFFAOYSA-K 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052768 actinide Inorganic materials 0.000 description 2
- 150000001255 actinides Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000005234 alkyl aluminium group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- DWCMDRNGBIZOQL-UHFFFAOYSA-N dimethylazanide;zirconium(4+) Chemical compound [Zr+4].C[N-]C.C[N-]C.C[N-]C.C[N-]C DWCMDRNGBIZOQL-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- UMJJFEIKYGFCAT-UHFFFAOYSA-N indan-2-one Chemical compound C1=CC=C2CC(=O)CC2=C1 UMJJFEIKYGFCAT-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052747 lanthanoid Inorganic materials 0.000 description 2
- 150000002602 lanthanoids Chemical class 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229920006030 multiblock copolymer Polymers 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000005204 segregation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002195 soluble material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000000194 supercritical-fluid extraction Methods 0.000 description 2
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- 239000012815 thermoplastic material Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 2
- 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
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- 230000004048 modification Effects 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000010653 organometallic reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical group [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000000646 scanning calorimetry Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- QYHQXFIOJJBRLJ-UHFFFAOYSA-N trimethyl-[3-(1-methyl-1h-inden-2-yl)-5-trimethylsilylphenyl]silane Chemical compound C=1C2=CC=CC=C2C(C)C=1C1=CC([Si](C)(C)C)=CC([Si](C)(C)C)=C1 QYHQXFIOJJBRLJ-UHFFFAOYSA-N 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- 238000007514 turning Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 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
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
-
- 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
- C08F10/02—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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
- C08F4/65922—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not
- C08F4/65927—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not two cyclopentadienyl rings being mutually bridged
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Abstract
Copolymère d'éthylène et d'au moins un comonomère contenant au moins 4 atomes de carbone, qui est caractérisé par une polydispersité supérieure à 2, une large transition du point de fusion telle que mesurée par l'analyse calorimétrique différentielle à compensation de puissance, et une répartition étroite de la composition. Des copolymères éthylène/C¿4+? peuvent également présenter au moins un point de fusion maximal supérieur au point de fusion maximal d'un copolymère statistique ayant la même composition d'unités monomères. Ces copolymères sont obtenus par mise en contact d'éthylène et d'un comonomère dans des conditions de polymérisation en présence d'un système de fluxion catalyseur approprié.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/227,228 US6169151B1 (en) | 1998-01-09 | 1999-01-08 | High-melting polyolefin copolymer elastomers, catalysts and methods of synthesis |
| US13710799P | 1999-06-02 | 1999-06-02 | |
| US09/227,228 | 1999-06-02 | ||
| US60/137,107 | 1999-06-02 | ||
| PCT/US1999/015518 WO2000040625A1 (fr) | 1999-01-08 | 1999-07-08 | Copolymeres d'ethylene a repartition etroite de la composition et a temperatures de fusion elevees, et procedes de production desdits copolymeres |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2322496A1 true CA2322496A1 (fr) | 2000-07-13 |
Family
ID=26834934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002322496A Abandoned CA2322496A1 (fr) | 1999-01-08 | 1999-07-08 | Copolymeres d'ethylene a repartition etroite de la composition et a temperatures de fusion elevees, et procedes de production desdits copolymeres |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1062257A1 (fr) |
| JP (1) | JP2002534538A (fr) |
| AU (1) | AU4979399A (fr) |
| CA (1) | CA2322496A1 (fr) |
| WO (1) | WO2000040625A1 (fr) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1138702A1 (fr) * | 2000-03-30 | 2001-10-04 | Fina Research S.A. | Polyéthylène préparé à l'aide d'un catalyseur métallocène pour fabriquer des containers plastiques brillants |
| WO2004026923A2 (fr) | 2002-09-20 | 2004-04-01 | Exxonmobil Chemical Patents Inc. | Processus de polymerisation supercritique et polymeres ainsi produits |
| BRPI0513057A (pt) | 2004-07-08 | 2008-04-22 | Exxonmobil Chem Patents Inc | produção de polìmero em condições supercrìticas |
| US8143352B2 (en) | 2006-12-20 | 2012-03-27 | Exxonmobil Research And Engineering Company | Process for fluid phase in-line blending of polymers |
| US8080610B2 (en) | 2007-03-06 | 2011-12-20 | Exxonmobil Research And Engineering Company | Monomer recycle process for fluid phase in-line blending of polymers |
| CN101855249B (zh) | 2007-09-13 | 2013-02-13 | 埃克森美孚研究工程公司 | 在线生产增塑聚合物和增塑聚合物共混物的方法 |
| EP2201042B1 (fr) | 2007-09-13 | 2012-06-27 | ExxonMobil Research and Engineering Company | Melange en ligne de plastifiants avec un polymere de base |
| CN101945942B (zh) | 2007-12-20 | 2012-08-08 | 埃克森美孚研究工程公司 | 生产粒料稳定的聚烯烃的在线方法 |
| US8138269B2 (en) | 2007-12-20 | 2012-03-20 | Exxonmobil Research And Engineering Company | Polypropylene ethylene-propylene copolymer blends and in-line process to produce them |
| US7910679B2 (en) | 2007-12-20 | 2011-03-22 | Exxonmobil Research And Engineering Company | Bulk homogeneous polymerization process for ethylene propylene copolymers |
| JP6607615B2 (ja) * | 2014-05-30 | 2019-11-20 | 株式会社ブリヂストン | 金属錯体触媒及びそれを用いた重合方法 |
| CN117567961B (zh) * | 2024-01-15 | 2024-04-09 | 万华化学集团股份有限公司 | 一种光伏胶膜用乙烯/α-烯烃无规共聚物及其应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0406912B1 (fr) * | 1986-09-24 | 1994-11-30 | Mitsui Petrochemical Industries, Ltd. | Procédé de polymérisation d'oléfines |
| US5451555A (en) * | 1991-06-27 | 1995-09-19 | Nippon Oil Co., Ltd. | Catalyst components for polymerization of olefins |
| CA2168883C (fr) * | 1993-08-06 | 2000-07-04 | Moses Olukayode Jejelowo | Catalyseurs de polymerisation; preparation et utilisation |
| US5594080A (en) * | 1994-03-24 | 1997-01-14 | Leland Stanford, Jr. University | Thermoplastic elastomeric olefin polymers, method of production and catalysts therefor |
| ES2182950T3 (es) * | 1995-05-16 | 2003-03-16 | Univation Tech Llc | Produccion de polietileno utilizando metalocenos estereosomericos. |
| US6225410B1 (en) * | 1997-12-25 | 2001-05-01 | Mitsui Chemicals | Ethylene/α-olefin copolymer and process for preparing the same |
| WO1999035171A1 (fr) * | 1998-01-09 | 1999-07-15 | The Board Of Trustees Of The Leland Stanford Jr. University | Elastomeres copolymeres polyolefiniques a point de fusion eleve, catalyseurs et procedes de synthese |
-
1999
- 1999-07-08 EP EP99933817A patent/EP1062257A1/fr not_active Withdrawn
- 1999-07-08 AU AU49793/99A patent/AU4979399A/en not_active Abandoned
- 1999-07-08 JP JP2000592333A patent/JP2002534538A/ja not_active Withdrawn
- 1999-07-08 WO PCT/US1999/015518 patent/WO2000040625A1/fr not_active Ceased
- 1999-07-08 CA CA002322496A patent/CA2322496A1/fr not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000040625A1 (fr) | 2000-07-13 |
| AU4979399A (en) | 2000-07-24 |
| JP2002534538A (ja) | 2002-10-15 |
| EP1062257A1 (fr) | 2000-12-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |