WO2003040201A1 - Isotactic propylene copolymers, their preparation and use - Google Patents
Isotactic propylene copolymers, their preparation and use Download PDFInfo
- Publication number
- WO2003040201A1 WO2003040201A1 PCT/US2002/014158 US0214158W WO03040201A1 WO 2003040201 A1 WO2003040201 A1 WO 2003040201A1 US 0214158 W US0214158 W US 0214158W WO 03040201 A1 WO03040201 A1 WO 03040201A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- copolymer
- ethylene
- propylene
- reactor
- weight percent
- Prior art date
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 303
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 title claims description 254
- 238000002360 preparation method Methods 0.000 title description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 365
- 229920000642 polymer Polymers 0.000 claims abstract description 308
- -1 propylene, ethylene Chemical group 0.000 claims abstract description 199
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 144
- 229920001155 polypropylene Polymers 0.000 claims abstract description 120
- 239000003446 ligand Substances 0.000 claims abstract description 109
- 239000004743 Polypropylene Substances 0.000 claims abstract description 52
- 239000013078 crystal Substances 0.000 claims abstract description 26
- 239000011954 Ziegler–Natta catalyst Substances 0.000 claims abstract description 25
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims abstract description 24
- 230000001965 increasing effect Effects 0.000 claims abstract description 23
- 238000002441 X-ray diffraction Methods 0.000 claims abstract description 22
- 239000000835 fiber Substances 0.000 claims abstract description 22
- 230000007423 decrease Effects 0.000 claims abstract description 20
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims abstract description 19
- 239000006260 foam Substances 0.000 claims abstract description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 254
- 239000005977 Ethylene Substances 0.000 claims description 253
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 243
- 238000000034 method Methods 0.000 claims description 184
- 230000008569 process Effects 0.000 claims description 118
- 238000006243 chemical reaction Methods 0.000 claims description 100
- 239000000203 mixture Substances 0.000 claims description 86
- 239000000178 monomer Substances 0.000 claims description 83
- 238000006116 polymerization reaction Methods 0.000 claims description 80
- 239000001257 hydrogen Substances 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 125000003118 aryl group Chemical group 0.000 claims description 64
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 54
- 125000003107 substituted aryl group Chemical group 0.000 claims description 52
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 48
- 229920001038 ethylene copolymer Polymers 0.000 claims description 47
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 47
- 229910052751 metal Inorganic materials 0.000 claims description 46
- 239000002184 metal Substances 0.000 claims description 45
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 40
- 125000004104 aryloxy group Chemical group 0.000 claims description 39
- 229920001384 propylene homopolymer Polymers 0.000 claims description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
- 125000004429 atom Chemical group 0.000 claims description 33
- 229920005606 polypropylene copolymer Polymers 0.000 claims description 30
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 29
- 238000009826 distribution Methods 0.000 claims description 26
- 229910052735 hafnium Inorganic materials 0.000 claims description 26
- 125000000707 boryl group Chemical group B* 0.000 claims description 24
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 22
- 239000004711 α-olefin Substances 0.000 claims description 22
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 18
- 238000005481 NMR spectroscopy Methods 0.000 claims description 17
- 230000001747 exhibiting effect Effects 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 229910052726 zirconium Inorganic materials 0.000 claims description 17
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- 239000002002 slurry Substances 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 229920001519 homopolymer Polymers 0.000 claims description 13
- 229920002959 polymer blend Polymers 0.000 claims description 12
- 150000001993 dienes Chemical class 0.000 claims description 11
- 239000012190 activator Substances 0.000 claims description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- 238000012685 gas phase polymerization Methods 0.000 claims description 4
- 229920005629 polypropylene homopolymer Polymers 0.000 claims description 4
- 239000002685 polymerization catalyst Substances 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 8
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 11
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- 229940093470 ethylene Drugs 0.000 description 179
- 239000000243 solution Substances 0.000 description 112
- 238000002844 melting Methods 0.000 description 98
- 230000008018 melting Effects 0.000 description 97
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- 239000002904 solvent Substances 0.000 description 83
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 73
- 239000010408 film Substances 0.000 description 66
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
- 239000000523 sample Substances 0.000 description 45
- 150000001875 compounds Chemical class 0.000 description 39
- 238000000113 differential scanning calorimetry Methods 0.000 description 38
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 29
- 229910052782 aluminium Inorganic materials 0.000 description 28
- 239000000460 chlorine Substances 0.000 description 27
- 150000002431 hydrogen Chemical class 0.000 description 26
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 24
- 230000003213 activating effect Effects 0.000 description 24
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
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- 125000001183 hydrocarbyl group Chemical group 0.000 description 20
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- 239000000126 substance Substances 0.000 description 20
- 229920000573 polyethylene Polymers 0.000 description 19
- 239000002243 precursor Substances 0.000 description 19
- 238000004458 analytical method Methods 0.000 description 18
- 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 18
- 229920001971 elastomer Polymers 0.000 description 17
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 17
- 239000012071 phase Substances 0.000 description 17
- 239000000806 elastomer Substances 0.000 description 16
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 230000002829 reductive effect Effects 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 15
- 238000001816 cooling Methods 0.000 description 14
- 238000003780 insertion Methods 0.000 description 14
- 238000004260 weight control Methods 0.000 description 14
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- 238000010828 elution Methods 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 239000002879 Lewis base Substances 0.000 description 12
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 12
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- LIKMAJRDDDTEIG-UHFFFAOYSA-N n-hexene Natural products CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 11
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- RERMPCBBVZEPBS-UHFFFAOYSA-N tris(2,6-dimethylphenyl)phosphane Chemical compound CC1=CC=CC(C)=C1P(C=1C(=CC=CC=1C)C)C1=C(C)C=CC=C1C RERMPCBBVZEPBS-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- OLFPYUPGPBITMH-UHFFFAOYSA-N tritylium Chemical compound C1=CC=CC=C1[C+](C=1C=CC=CC=1)C1=CC=CC=C1 OLFPYUPGPBITMH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/32—Layered products comprising a layer of synthetic resin comprising polyolefins
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Priority Applications (2)
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JP2003542246A JP2005508415A (ja) | 2001-11-06 | 2002-05-06 | アイソタクチックプロピレンコポリマー類、その製法および用途 |
EP02725927A EP1444276A1 (en) | 2001-11-06 | 2002-05-06 | Isotactic propylene copolymers, their preparation and use |
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US33888101P | 2001-11-06 | 2001-11-06 | |
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Cited By (191)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2004014998A2 (en) | 2002-08-12 | 2004-02-19 | Exxonmobil Chemical Patents Inc. | Plasticized polyolefin compositions |
WO2004026925A1 (en) * | 2002-09-17 | 2004-04-01 | Dow Global Technologies Inc. | Improved process for manufacture of polymers |
WO2004041928A1 (en) * | 2002-11-05 | 2004-05-21 | Dow Global Technologies Inc. | Thermoplastic elastomer compositions |
WO2004099309A1 (en) * | 2003-05-05 | 2004-11-18 | Dow Global Technologies Inc. | Filled thermoplastic olefin composition |
WO2005080495A1 (en) | 2004-02-12 | 2005-09-01 | Exxonmobil Chemical Patents Inc. | Plasticized polyolefin compositions |
JP2005263771A (ja) * | 2004-02-18 | 2005-09-29 | Shinko Kagaku Kogyo Kk | 高純度テトラキス(ジアルキルアミノ)ハフニウムの製造法 |
JP2005298467A (ja) * | 2004-04-12 | 2005-10-27 | Kojundo Chem Lab Co Ltd | 高純度テトラキスジメチルアミノハフニウムとその製造方法およびそれを用いたゲート絶縁膜の製造方法。 |
WO2005103123A1 (en) * | 2004-04-19 | 2005-11-03 | Dow Golbal Technologies Inc. | Composition suitable for single-sided, low-noise, stretch cling film and films made therefrom |
WO2006009976A1 (en) * | 2004-06-21 | 2006-01-26 | Exxonmobil Chemical Patents Inc. | Polymerization process |
US6994763B2 (en) | 2002-10-24 | 2006-02-07 | Advanced Design Concept Gmbh | Elastomeric multicomponent fibers, nonwoven webs and nonwoven fabrics |
EP1655341A1 (en) | 2004-11-05 | 2006-05-10 | Advanced Elastomer Systems, L.P. | Transparent polyolefin compositions |
WO2006057369A1 (ja) | 2004-11-26 | 2006-06-01 | Mitsui Chemicals, Inc. | ポリプロピレンの不織布およびその用途 |
WO2006065649A1 (en) | 2004-12-17 | 2006-06-22 | Exxonmobil Chemical Patents Inc. | Heterogeneous polymer blends and molded articles therefrom |
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Also Published As
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US20070249798A1 (en) | 2007-10-25 |
CN101319050A (zh) | 2008-12-10 |
US20050054800A1 (en) | 2005-03-10 |
CN101319071B (zh) | 2011-08-17 |
US20040082750A1 (en) | 2004-04-29 |
US7897679B2 (en) | 2011-03-01 |
US6919407B2 (en) | 2005-07-19 |
US20030194575A1 (en) | 2003-10-16 |
US6946535B2 (en) | 2005-09-20 |
SG147306A1 (en) | 2008-11-28 |
EP1444276A1 (en) | 2004-08-11 |
JP2005508415A (ja) | 2005-03-31 |
US20060004167A1 (en) | 2006-01-05 |
US7041765B2 (en) | 2006-05-09 |
CN101319071A (zh) | 2008-12-10 |
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