CN103502281A - 新型催化剂和使用其生产乙烯基封端的聚合物的方法 - Google Patents
新型催化剂和使用其生产乙烯基封端的聚合物的方法 Download PDFInfo
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- CN103502281A CN103502281A CN201280016041.9A CN201280016041A CN103502281A CN 103502281 A CN103502281 A CN 103502281A CN 201280016041 A CN201280016041 A CN 201280016041A CN 103502281 A CN103502281 A CN 103502281A
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- Prior art keywords
- racemize
- indenyl
- borate
- dimethyl
- methyl
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- 239000012190 activator Substances 0.000 claims abstract description 110
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- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims abstract description 105
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 49
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- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims description 14
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 13
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- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 12
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
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- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 8
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- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 7
- 230000000379 polymerizing effect Effects 0.000 claims description 7
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000002091 cationic group Chemical group 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 abstract description 51
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 2
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- 150000004678 hydrides Chemical class 0.000 abstract 1
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- 239000000126 substance Substances 0.000 description 123
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000006197 hydroboration reaction Methods 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 229920000092 linear low density polyethylene Polymers 0.000 description 1
- 239000004707 linear low-density polyethylene Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012685 metal catalyst precursor Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000012968 metallocene catalyst Substances 0.000 description 1
- 150000002738 metalloids Chemical group 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- OXQMIXBVXHWDPX-UHFFFAOYSA-N n,n,2-trimethylpropan-2-amine Chemical compound CN(C)C(C)(C)C OXQMIXBVXHWDPX-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical group CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910052615 phyllosilicate Inorganic materials 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000005353 silylalkyl group Chemical group 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000006557 surface reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/04—Monomers containing three or four carbon atoms
- C08F10/06—Propene
-
- 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
- C08F4/65908—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2314/00—Polymer mixtures characterised by way of preparation
- C08L2314/06—Metallocene or single site catalysts
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/072,280 US8455597B2 (en) | 2011-03-25 | 2011-03-25 | Catalysts and methods of use thereof to produce vinyl terminated polymers |
| US13/072,280 | 2011-03-25 | ||
| EP11167019 | 2011-05-23 | ||
| EP11167019.6 | 2011-05-23 | ||
| PCT/US2012/027685 WO2012134719A2 (en) | 2011-03-25 | 2012-03-05 | Novel catalysts and methods of use thereof to produce vinyl terminated polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103502281A true CN103502281A (zh) | 2014-01-08 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| CN201280016041.9A Pending CN103502281A (zh) | 2011-03-25 | 2012-03-05 | 新型催化剂和使用其生产乙烯基封端的聚合物的方法 |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP2688916A4 (de) |
| JP (1) | JP5848815B2 (de) |
| CN (1) | CN103502281A (de) |
| WO (1) | WO2012134719A2 (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114555651A (zh) * | 2020-08-04 | 2022-05-27 | 株式会社Lg化学 | 混合负载型茂金属催化剂和使用其制备聚丙烯的方法 |
| CN115485311A (zh) * | 2020-02-24 | 2022-12-16 | 埃克森美孚化学专利公司 | 用于生产乙烯叉基封端的聚α-烯烃的柄型-双(茚-2-基)催化剂 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102964371B (zh) * | 2012-12-17 | 2015-08-12 | 上海化工研究院 | 一种硅桥连位阻型环戊二烯类化合物的制备方法 |
| JP2016530360A (ja) | 2013-07-17 | 2016-09-29 | エクソンモービル ケミカル パテンツ インコーポレイテッド | 置換メタロセン触媒を使用する方法およびそれに由来する生成物 |
| CN113544173A (zh) | 2019-03-12 | 2021-10-22 | 三井化学株式会社 | 烯烃系树脂、其交联物及它们的制造方法 |
| KR102819366B1 (ko) * | 2020-10-08 | 2025-06-10 | 주식회사 엘지화학 | 신규한 메탈로센 화합물, 이를 포함하는 촉매 조성물 및 이를 이용한 올레핀 중합체의 제조 방법 |
| JP7681097B2 (ja) | 2021-03-31 | 2025-05-21 | 三井化学株式会社 | エチレン－α－オレフィン共重合体、熱可塑性樹脂組成物、フィルムおよび積層体 |
| WO2022210844A1 (ja) | 2021-03-31 | 2022-10-06 | 三井化学株式会社 | エチレン－α－オレフィン共重合体、熱可塑性樹脂組成物、およびフィルム |
| US20240191068A1 (en) | 2021-03-31 | 2024-06-13 | Mitsui Chemicals, Inc. | Ethylene resin composition and shaped article |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1127082B1 (de) * | 1998-11-02 | 2005-01-19 | ExxonMobil Chemical Patents Inc. | Ionische katalysatorzusammensetzungen auf träger |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0003603A3 (en) * | 1997-03-29 | 2002-03-28 | Montell Technology Company Bv | Metallocenes and catalysts for polymerization of olefins |
| BR9908807A (pt) * | 1998-03-11 | 2000-10-31 | Dow Chemical Co | Processo integrado para preparação de complexos de dienos |
| JP2000038420A (ja) * | 1998-07-24 | 2000-02-08 | Idemitsu Petrochem Co Ltd | プロピレン系共重合体及びその製造方法 |
| JP2000038411A (ja) * | 1998-07-24 | 2000-02-08 | Idemitsu Petrochem Co Ltd | オレフィン重合用触媒及びポリオレフィンの製造方法 |
| US7589160B2 (en) * | 2002-12-04 | 2009-09-15 | Basell Polyolefine Gmbh | Process for preparing 1-butene polymers |
| JP4667901B2 (ja) * | 2005-02-18 | 2011-04-13 | 出光興産株式会社 | 不飽和炭化水素化合物の製造方法 |
| US7943711B2 (en) * | 2007-05-14 | 2011-05-17 | Exxonmobil Chemical Patents Inc. | Ethylene elastomer compositions |
-
2012
- 2012-03-05 JP JP2014501092A patent/JP5848815B2/ja not_active Expired - Fee Related
- 2012-03-05 WO PCT/US2012/027685 patent/WO2012134719A2/en active Application Filing
- 2012-03-05 EP EP12763666.0A patent/EP2688916A4/de not_active Withdrawn
- 2012-03-05 CN CN201280016041.9A patent/CN103502281A/zh active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1127082B1 (de) * | 1998-11-02 | 2005-01-19 | ExxonMobil Chemical Patents Inc. | Ionische katalysatorzusammensetzungen auf träger |
Non-Patent Citations (1)
| Title |
|---|
| WENG, W. ET AL.: "Long Chain Branched Isotactic Polypropylene", 《MACROMOLECULES》, vol. 35, no. 10, 16 April 2002 (2002-04-16), pages 3838 - 3843, XP002668104, DOI: 10.1021/ma020050j * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115485311A (zh) * | 2020-02-24 | 2022-12-16 | 埃克森美孚化学专利公司 | 用于生产乙烯叉基封端的聚α-烯烃的柄型-双(茚-2-基)催化剂 |
| CN114555651A (zh) * | 2020-08-04 | 2022-05-27 | 株式会社Lg化学 | 混合负载型茂金属催化剂和使用其制备聚丙烯的方法 |
| CN114555651B (zh) * | 2020-08-04 | 2023-10-24 | 株式会社Lg化学 | 混合负载型茂金属催化剂和使用其制备聚丙烯的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2012134719A8 (en) | 2014-03-27 |
| WO2012134719A3 (en) | 2012-11-22 |
| EP2688916A2 (de) | 2014-01-29 |
| WO2012134719A2 (en) | 2012-10-04 |
| JP2014513735A (ja) | 2014-06-05 |
| EP2688916A4 (de) | 2014-10-22 |
| JP5848815B2 (ja) | 2016-01-27 |
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