JP2000053691A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2000053691A5 JP2000053691A5 JP1999062448A JP6244899A JP2000053691A5 JP 2000053691 A5 JP2000053691 A5 JP 2000053691A5 JP 1999062448 A JP1999062448 A JP 1999062448A JP 6244899 A JP6244899 A JP 6244899A JP 2000053691 A5 JP2000053691 A5 JP 2000053691A5
- Authority
- JP
- Japan
- Prior art keywords
- indenyl
- bis
- group
- ethylene
- formula
- 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.)
- Withdrawn
Links
- -1 zirconocene compound Chemical class 0.000 description 20
- 239000003446 ligand Substances 0.000 description 15
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 9
- IDASTKMEQGPVRR-UHFFFAOYSA-N cyclopenta-1,3-diene;zirconium(2+) Chemical class [Zr+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 IDASTKMEQGPVRR-UHFFFAOYSA-N 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 238000002360 preparation method 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
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910007926 ZrCl Inorganic materials 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- UMGHCEPAQJUHNV-UHFFFAOYSA-N 2,5-dibenzylhexanedioic acid Chemical compound C=1C=CC=CC=1CC(C(=O)O)CCC(C(O)=O)CC1=CC=CC=C1 UMGHCEPAQJUHNV-UHFFFAOYSA-N 0.000 description 1
- KXHNSSHBYAVFMS-UHFFFAOYSA-N 2-[2-(1h-inden-2-yl)ethyl]-1h-indene Chemical compound C1=CC=C2CC(CCC=3CC4=CC=CC=C4C=3)=CC2=C1 KXHNSSHBYAVFMS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 241001553014 Myrsine salicina Species 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- ISVZDGPFUTWGQZ-UHFFFAOYSA-L [Cl-].[Cl-].C(C)C1C(=CC2=CC=CC=C12)[Zr+2] Chemical compound [Cl-].[Cl-].C(C)C1C(=CC2=CC=CC=C12)[Zr+2] ISVZDGPFUTWGQZ-UHFFFAOYSA-L 0.000 description 1
- NCQVVJSDCROOHI-UHFFFAOYSA-L [Cl-].[Cl-].C1(=CC=CC=C1)C1=C2C=C(CC2=CC=C1)[Zr+2] Chemical compound [Cl-].[Cl-].C1(=CC=CC=C1)C1=C2C=C(CC2=CC=C1)[Zr+2] NCQVVJSDCROOHI-UHFFFAOYSA-L 0.000 description 1
- HTTMSKJHZCLOIF-UHFFFAOYSA-L [Cl-].[Cl-].CC1C(=CC2=C(C=CC=C12)C1=CC=CC=C1)[Zr+2] Chemical compound [Cl-].[Cl-].CC1C(=CC2=C(C=CC=C12)C1=CC=CC=C1)[Zr+2] HTTMSKJHZCLOIF-UHFFFAOYSA-L 0.000 description 1
- LAZAWKSPFMUFGD-UHFFFAOYSA-L [Cl-].[Cl-].CC1C(=CC2=CC=CC=C12)[Zr+2] Chemical compound [Cl-].[Cl-].CC1C(=CC2=CC=CC=C12)[Zr+2] LAZAWKSPFMUFGD-UHFFFAOYSA-L 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- PESYEWKSBIWTAK-UHFFFAOYSA-N cyclopenta-1,3-diene;titanium(2+) Chemical compound [Ti+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 PESYEWKSBIWTAK-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 150000003839 salts Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98200728.8 | 1998-03-09 | ||
| EP98200728 | 1998-03-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000053691A JP2000053691A (ja) | 2000-02-22 |
| JP2000053691A5 true JP2000053691A5 (enExample) | 2006-04-20 |
Family
ID=8233448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11062448A Withdrawn JP2000053691A (ja) | 1998-03-09 | 1999-03-09 | 架橋ジルコノセン化合物類、それらの製造法およびオレフィン重合における触媒成分としてのそれらの用途 |
Country Status (4)
| Country | Link |
|---|---|
| US (3) | US6232484B1 (enExample) |
| JP (1) | JP2000053691A (enExample) |
| DE (1) | DE69904521T2 (enExample) |
| ES (1) | ES2188047T3 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6342622B1 (en) * | 1999-06-11 | 2002-01-29 | Dsm B.V. | Indenyl compounds for the polymerization of olefins |
| EP1214364B1 (en) * | 1999-09-22 | 2003-07-16 | Basell Polyolefine GmbH | Catalyst system and process for the polymerization of olefins |
| WO2003008465A2 (en) * | 2001-07-19 | 2003-01-30 | Univation Technologies, Llc | Low comonomer incorporating metallocene catalyst compounds |
| US6559251B1 (en) * | 2002-08-02 | 2003-05-06 | Equistar Chemicals, Lp | Process for making low-density polyolefins |
| US7176158B2 (en) * | 2002-10-25 | 2007-02-13 | Exxonmobil Chemical Patents Inc. | Polymerization catalyst composition |
| CN100457789C (zh) * | 2004-10-27 | 2009-02-04 | 中国石油化工股份有限公司 | 用于烯烃聚合的催化剂组分及其催化剂 |
| DE602005013222D1 (de) * | 2005-08-17 | 2009-04-23 | Saudi Basic Ind Corp | Polymerisations- und Herstellungsverfahren einer Katalysatorzusammensetzung zur Polymerisation von Olefinen |
| CN104080792A (zh) * | 2011-12-19 | 2014-10-01 | 沙特基础工业公司 | 用于制备茂金属络合物的方法 |
| CN104093730A (zh) * | 2011-12-19 | 2014-10-08 | 沙特基础工业公司 | 用于制备茂金属络合物的方法 |
| JP6326202B2 (ja) * | 2013-05-16 | 2018-05-16 | 三井化学株式会社 | オレフィン重合用固体触媒成分およびそれを用いたオレフィン系重合体の製造方法 |
| GB201407000D0 (en) | 2014-04-17 | 2014-06-04 | Isis Innovation | Catalysts |
| CN104370681A (zh) * | 2014-09-29 | 2015-02-25 | 中国科学院上海高等研究院 | 一种乙烯基桥联的二烷基茚化合物的合成方法 |
| EP3184556B1 (en) | 2014-12-12 | 2019-07-24 | LG Chem, Ltd. | Metallocene-supported catalyst and method of preparing polyolefin using the same |
| KR20170102956A (ko) | 2015-01-06 | 2017-09-12 | 에스씨지 케미컬스 컴퍼니, 리미티드. | SiO2-층상 이중 수산화물 마이크로스피어 및 에틸렌 중합 반응에서의 촉매 지지체로의 이들의 용도 |
| EP3492532A1 (en) | 2015-01-06 | 2019-06-05 | Scg Chemicals Co. Ltd. | Sio2-layered double hydroxide microspheres and methods of making them |
| GB201608384D0 (en) | 2016-05-12 | 2016-06-29 | Scg Chemicals Co Ltd | Unsymmetrical metallocene catalysts and uses thereof |
| CN110650978B (zh) * | 2017-04-04 | 2022-09-23 | Sabic环球技术有限责任公司 | 用于烯烃聚合的二甲基-甲硅烷基-桥连的-1-取代-2-茚基茂金属复合物 |
| CN110650965B (zh) | 2017-04-04 | 2022-10-04 | Sabic环球技术有限责任公司 | 用于烯烃聚合的二烃基-甲硅烷基-桥连-1,3二取代-2-茚基茂金属络合物 |
| EP4110834B1 (en) | 2020-02-24 | 2024-04-03 | ExxonMobil Chemical Patents Inc. | Ansa-bis(inden-2-yl) catalysts for producing vinylidene-terminated polyalphaolefins |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3840772A1 (de) | 1988-12-03 | 1990-06-07 | Hoechst Ag | Verfahren zur herstellung einer heterogenen metallocenkatalysatorkomponente |
| ES2071888T3 (es) | 1990-11-12 | 1995-07-01 | Hoechst Ag | Bisindenilmetalocenos sustituidos en posicion 2, procedimiento para su preparacion y su utilizacion como catalizadores en la polimerizacion de olefinas. |
| NL9201970A (nl) * | 1992-11-11 | 1994-06-01 | Dsm Nv | Indenylverbindingen en katalysatorcomponenten voor de polymerisatie van olefinen. |
| IT1290856B1 (it) * | 1996-12-19 | 1998-12-14 | Enichem Spa | Metalloceni, loro preparazione ed uso nella polimerizzazione di alfa-olefine |
| ES2198098T3 (es) * | 1998-03-09 | 2004-01-16 | Basell Poliolefine Italia S.P.A. | Procedimiento multietapas para la polimerizacion de olefinas. |
-
1999
- 1999-03-03 DE DE69904521T patent/DE69904521T2/de not_active Expired - Fee Related
- 1999-03-03 ES ES99104222T patent/ES2188047T3/es not_active Expired - Lifetime
- 1999-03-09 JP JP11062448A patent/JP2000053691A/ja not_active Withdrawn
- 1999-03-09 US US09/265,046 patent/US6232484B1/en not_active Expired - Fee Related
-
2001
- 2001-02-28 US US09/795,894 patent/US6306791B2/en not_active Expired - Fee Related
- 2001-10-05 US US09/972,336 patent/US6673880B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2000053691A5 (enExample) | ||
| US6262195B1 (en) | Multi-stage process for the polymerization of olefins | |
| JP3371118B2 (ja) | 配位子としてベンゼン融合したインデニル誘導体を持つメタロセン、その製造方法および触媒としてのその用途 | |
| JP4169791B2 (ja) | オレフィン重合用メタロセンと触媒 | |
| JP3234876B2 (ja) | ブリッジのあるキラルなメタロセン、その製造方法およびそれの触媒としての用途 | |
| JP4167254B2 (ja) | アリール置換インデニル誘導体をリガンドとして含んだメタロセンの合成のための中間体およびその使用方法 | |
| US6316562B1 (en) | Catalyst systems for (co-)polymerization reactions, metallocene amide halogenides, the production and use thereof | |
| JP3270049B2 (ja) | Ｃ２〜ｃ１０−アルク−１−エンの重合のための触媒系 | |
| EP1567560B1 (en) | Organometallic transition metal compound, biscyclopentadienyl ligand system, catalyst system and process for preparing polyolefins | |
| AU656033B2 (en) | Group IVA metal compounds and catalyst compositions based thereon | |
| HUT71642A (en) | Organometallic fluorenyl compounds, preparation, and use | |
| JP2002265486A (ja) | リガンドとして二環シクロペンタジエン誘導体を持つメタロセンおよびそれの触媒としての用途 | |
| US6232484B1 (en) | Bridged zirconocene compounds, process for their preparation and their use as catalyst components in the polymerization of olefins | |
| ITMI950410A1 (it) | Composti metallocenici bis-fluorenilici procedimento per la loro preparazione e loro utilizzo in catalizzatori per la polimerizzazione | |
| EP1047702A1 (en) | Bis(tetrahyydro-indenyl) metallocenes as olefin-polymerization- catalyst | |
| JP2001525801A (ja) | 立体剛性メタロセン化合物 | |
| JP4202320B2 (ja) | フルベン、メタロセン触媒とその製造方法、及びこれを用いたポリオレフィン共重合体の製造方法 | |
| JPH1060033A (ja) | 低い分子量を有するポリオレフイン類の製造方法および触媒 | |
| EP0942011B1 (en) | Multi-stage process for the polymerization of olefins | |
| EP1059300A1 (en) | Indenyl compounds for the polymerisation of olefins | |
| EP0941997B1 (en) | Bridged zirconocene compounds, process for their preparation, and their use as catalyst components in the polymerization of olefins | |
| JP2000119289A (ja) | 新規なメタロセン及びその調製方法 | |
| EP2204375A1 (en) | Preparation of mono-aryl-substituted methylene-bridged substituted cyclopentadienyl-fluorenyl ligands and zirconium complexes derived thereof | |
| US20110251400A1 (en) | Preparation of Dphenyl-Bridged Substituted Cyclopentadienyil-Fluorenyl Ligands | |
| KR20000016125A (ko) | 메탈로센 및 올레핀 중합용 촉매_ |