Bridged bi-aromatic ligands, catalysts, processes for polymerizing and polymers therefrom

Patent 7659415 Issued on February 9, 2010. Estimated Expiration Date:

July 9, 2027. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.

Abstract Claims Description Full Text

Patent References

Catalysts for polymerizing propylene in a high temperature solution process
Patent #: 4297465
Issued on: 10/27/1981
Inventor: Smith

Titanium complexes and catalysts prepared therefrom
Patent #: 4452914
Issued on: 06/05/1984
Inventor: Coleman, III , et al.

Catalyst component for making primarily isotactic elastomeric polypropylene or polybutene
Patent #: 4971936
Issued on: 11/20/1990
Inventor: Wilson, et al.

Metal complex compounds
Patent #: 5064802
Issued on: 11/12/1991
Inventor: Stevens, et al.

Process for producing stereoregular polymers having a narrow molecular weight distribution
Patent #: 5093415
Issued on: 03/03/1992
Inventor: Brady, III, et al.

Catalyst system of enhanced productivity
Patent #: 5153157
Issued on: 10/06/1992
Inventor: Hlatky, et al.

Amido transition metal compound and a catalyst system for the production of isotatic polypropylene
Patent #: 5318935
Issued on: 06/07/1994
Inventor: Canich, et al.

Production of olefin polymers
Patent #: 5385993
Issued on: 01/31/1995
Inventor: Fujita

Catalyst composition
Patent #: 5453410
Issued on: 09/26/1995
Inventor: Kolthammer, et al.

Ionic metallocene catalyst compositions
Patent #: 5599761
Issued on: 02/04/1997
Inventor: Turner

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Inventors

Assignee

Symyx Solutions, Inc.

Application

No. 11775095 filed on 07/09/2007

US Classes:

556/51Titanium, zirconium, or hafnium containing (Ti, Zr, or Hf)

Examiners

Primary: Lu, Caixia

Attorney, Agent or Firm

ARMSTRONG TEASDALE LLP

Foreign Patent References

0277004 EP 08/01/1988
0534405 EP 03/01/1993
0582194 EP 02/01/1994
0622380 EP 11/01/1994
0292134 EP 11/01/1998
0922712 EP 06/01/1999
1110930 EP 06/01/2001
08134064 JP 05/01/1996
08217775 JP 08/01/1996
2002280179 JP 09/01/2002
9407926 WO 04/01/1994
9411409 WO 05/01/1994
9803521 WO 06/01/1998
9905186 WO 02/01/1999
9906413 WO 02/01/1999
9942467 WO 08/01/1999
0009255 WO 02/01/2000
0100581 WO 01/01/2001
0148028 WO 07/01/2001
0198371 WO 12/01/2001
0202576 WO 01/01/2002
0236638 WO 05/01/2002
02083306 WO 10/01/2002
02085820 WO 10/01/2002
2005108406 WO 11/01/2005
03091262 WO 05/01/2008

International Classes

C07F 7/00
C07F 7/28
C08F 4/60
B01J 31/22

Abstract

New ligands and compositions with bridged bis-aromatic ligands are disclosed that catalyze the polymerization of monomers into polymers. These catalysts with metal centers have high performance characteristics, including higher comonomer incorporation into ethylene/olefin copolymers, where such olefins are for example, 1-octene, propylene or styrene. The catalysts also polymerize propylene into isotactic polypropylene.

Other References

Zhang et al., “General Synthesis of Racemic Me(2)Si-Bridged Bis(indenyl) Zirconocene Complexes”, J. Am. Chem. Soc., vol. 122, 2000, pp. 8093-8094.
Yamashita et al., “Chiral Hetero Diels-Alder Products by Enantioselective and Diastereoselective Zirconium Catalysts. Scope, Limitation, Mechanism, and Application to the Concise Synthesis of (+)-Prelactone C and (+)-9-Deoxygoniopyprone”, J. Am. Chem. Soc., 125, 2003, pp. 3793-3798.
Wuff et al., “Active Site Design in a Chemzyme: Development of a Highly Asymmetric and Remarkably Temperature-Independent Catalyst for the Imino Aldol Reaction”, Agnew. Chem. Int. Ed., vol. 40, 2001, pp. 2271-2274.
Walter et al., “Novel Polypropylene Materials”, J.M.S.-Pure Appl. Chem., vol. A36, No. 11, 1999, pp. 1613-1639.
Walsh, “Titanium-Catalyzed Enantioselective Additions of Alkyl Groups to Aldehydes: Mechanistic Studies and New Concepts in Asymmetric Catalysis”, Acc. Chem. Res., vol. 36, No. 10, 2003, pp. 739-749.
Vathauer et al., “Extremely Active Polymerization of Propene by Bisindenzylzirconocenes and Tetra (pentafluorophenyl)-borate”, Polymer, vol. 42, 2001, pp. 4017-4024.
Ueda et al., “Doubly Helical, Chiral Crown Thioether Fully Preorganized for Planar Coordination”, J. Chem. Soc. Chem. Commun., 1995, pp. 935-936.
Takahashi et al., “An Expedient Route to Some Monoalkyl Ethers of Enantiomerically Pure Bi-Beta-Naphtol”, Tetrahedron Asymmetry, vol. 8, No. 18, 1997, pp. 3125-3130.
Svejda et al., “Ethylene Oligomerization and Propylene Dimerization Using Cationic (alpha)-Diimine)nickel(II) Catalysts”, Organmetallics, vol. 18, No. 1, 1999, pp. 65-74.
Sundell, “Isotacticity Determination of Polypropylene Using FT-Raman Spectroscopy”, Polymer, vol. 37, No. 15, 1996, pp. 3227-3231.
Stanforth, “Catalytic Cross-Coupling Reactions in Biaryl Synthesis”, Tetrahedron, vol. 54, 1998, pp. 263-303.
Scott et al., “Zirconium Catalysed Enantioselective Hydramination/Cyclisation”, Chem. Commun., 2004, pp. 894-895.
Schrock et al., “Synthesis of Titanium, Zirconium, and Hafnium Complexes That Contain Diamido Donor Ligands of the Type [(t-BuN-o-C6H4)2O]2- and an Evaluation of Activated Versions for the Polmerization of 1-Hexene”, Organometallics, vol. 18, 1999, pp. 3649-3670.
Ringwald et al., “Asymmetric Thermal Transformation, a New Way to Enantiopure Biphenyl-Bridged Titanocene and Zirconocene Complexes: Efficient Catalysts for Asymmetric Imine Hydrogenation ”, J. Am. Chem. Soc., vol. 121, No. 7, 1999, pp. 1524-1527.
Resconi et al., “Selectivity in Propene Polymerization with Metallocene Catalysts”, Chem. Rev., vol. 100, 2000, pp. 1253-1345.
Piers et al., “New Bifunctional Perfluoroaryl Boranes: Synthesis and Reactivity of the Ortho-Phenylene-Bridged Diboranes . . . ”, J. Am. Chem. Soc., vol. 121, 1999, pp. 3244-3245.
Pellecchia et al., “A Novel (n7) Coordination Mode of a Benzyl Ligand in a Cationic Zirconium Complex”, Organometallics, vol. 13, 1994, pp. 3773-3775.
Pellecchia et al., “Single Insertion of (alpha)- Olefins into the Cationic Complex [Zr(CH(2)Ph(3)] Affording Isolable [Zr(CH(2)Ph)(2)(CH(2)CHRCH(2)Ph)] + Adducts: A Model for the Insertion Mechanism in Ziegler-Natta Polymerization”, Organometallics, vol. 13, 1994, pp. 298-302.
Pellecchia et al., Synthesis, Crystal Structure, and Olefin Polymerization of a Zwitterionic(n6)-Arene Zirconium Tris (hydrocarbyl), J. Am. Chem. Soc., vol. 115, 1993, pp. 1160-1162.
Negishi, “Some Newer Aspects of Organizirconium Chemistry of Relevance to Organic Synthesis: Zr-Ca'alyzed Enantioselective Carbometallation”, Pure Appl. Chem., vol. 73, No. 2, 2001, pp. 239-242.
McGuinness et al., “First CR(III)-SNS Complexes and Their Use as Highly Efficient Catalysts for the Trimerization of Ethylene to 1-Hexene”, J. Am. Chem. Soc., vol. 125, No. 18, 2003, pp. 5272-5273.
McGuinness et al., “Novel Cr-PNP Complexes as Catalysts for the Trimerisation of Ethylene”, Chem. Commun., 2003, pp. 334-335.
Maruoka, “Asymmetric Reactions with Chiral Lewis Acis Catalysts,” Ojima (Ed.), Catalytic Asymmetric Synthesis, Chap. 9, 1993, pp. 413-440.
Marks et al., “Cocatalysts for Metal-Catalyzed Olefin Polymerization: Activators, Activation Processes, and Structure-Activity Relationships”, Chem. Rev., vol. 100, 2000, pp. 1391-1434.
Marek (Ed.), Titanium and Zirconium in Organic Synthesis, 2002, Wiley-VCH Verlag GmbH, Weinheim.
March (Ed.), Advanced Organic Chemistry, 4th Ed., 1992, Wiley, New York.
Luongo, “Infrared Study of Polypropylene”, J. Appl. Polym. Sci., vol. III, No. 9, 1960, pp. 302-309.
LoCoco et al., “Chelate-Controlled Synthesis of rac-and meso-Me(2)Si(3-(t) Bu-C(5) H(3))(2)ZrCl(2)”, Organometallics, vol. 22, 2003, pp. 5498-5503.
LaPointe et al., “New Family of Weakly coordinating Anions”, J. Am. Chem. Soc., vol. 122, 2000, pp. 9560-9561.
Kuber, “Metallocenes as a Source of Fine Chemicals”, Appl. Homogeneous Catalysis with Organometallic Compounds, Cornils & Herrmann (Eds.), vol. 2, 1996, pp. 893-902.
Kol et al., “Isospecific Living Polymerization of 1-Hexene by a Readily Available Nonmetallocene C(2)-Symmetrical Zirconium Catalyst”, J. Am. Chem. Soc., vol. 122, No. 43, 2000, pp. 10706-10707.
Knobler et al., “The Crystal and Molecular Structures of Bridged Spherands”, J. Incl. Phen. & Molec. Recog. in Chem., vol. 12, 1992, pp. 341-360.
Klapars et al., “A General and Efficient Copper Catalyst for the Amidation of Aryl Halides and the N-Arylation of Nitrogen Heterocycles”, J. Am. Chem. Soc., vol. 123, No. 31, 2001, pp. 7727-7729.
Kaminsky et al., “The Influence of the Polymerization Process on the Product Properties of Metallocene-Polypropene”, Chem. Eng. Technol., vol. 24. No. 11, 2001, pp. 1124-1128.
Jordan, “Chemistry of Cationic Dicyclopentadienyl Group 4 Metal-Alkyl Complexes”, Adv. Organometallic Chem., vol. 32, 1991, pp. 325-387.
Hoveyda, “Chiral Zirconium Catalysts for Enantioselective Synthesis”, Titanium and Zirconium in Organic Synthesis, Marek (Ed.), Wiley-VCH Verlang GmbH, Weinheim, 2002, pp. 180-229.
Hlatky, “Heterogeneous Single-Site Catalysts for Olefin Polymerization”, Chem. Rev., vol. 100, 2000, pp. 1347-1376.
Helgeson et al., “The Lithium Chloride Complex of the Anti Isomer of the Bridged Spherand C(50)H(48)O(6)”, Acta. Crystallographica Section C, vol. 56, 2000, pp. 795-797.
Gladysz, “Frontiers in Metal-Catalyzed Polymerization: Designer Metallocenes, Designs on New Monomers, Demystifying MAO, Metathesis Deshabille”, Chemical Reviews, vol. 100, No. 4, Apr. 2000, 2 pgs.
Gibson et al., “Advances in Non-Metallocene Olefin Polymerization Catalysis”, Chem. Rev., vol. 103, 2003, pp. 283-315.
Gibson et al., “The Search for New-Generation Olefin Polymerization Catalysts: Life Beyond Metallocenes”, Angew. Chem. Int. Ed. Engl., vol. 38, 1999, pp. 428-447.
Forni et al, “Kinetics and Mechanism of Propylene to 4-Methyl-1-pentene Catalytic Dimerization”, Ind. Eng. Chem. Process Des. Develop., vol. 12, 1973, pp. 455-459.
Fink, “Propene Polymerization with Silica-Supported Metallocene/MAO Catalysts”, Chem. Rev., vol. 100, 2000, pp. 1377-1390.
Ewen, “Evaluation of the Dimethylsilyl-Bis(2-Methyl-4-Phenyl-1-Indenyl) Ligand with Group 4 Triad Metals in Propene Polymerizations with Methylaluminoxane”, Macromol. Rapid Commun., vol. 19, 1998, pp. 71-73.
Diamond et al., “Efficient Synthesis of Chiral ansa-Metallocenes by Amine Elimination”, J. Am. Chem. Soc., vol. 118, 1996, pp. 8024-8033.
Deng et al., “Synthesis of High-Melting, Isotactic Polypropene with C(2)- and C(1)-Symmetrical Zirconocenes”, Macromolecules, vol. 29, 1996, pp. 6371-6376.
Deckers et al., “Catalytic Trimerization of Ethene with Highly Active Cyclopentadienyl-Arene Titanium Catalysts”, Organometallics, vol. 21, 2002, pp. 5122-5135.
Cram et al., “Host-Guest Complexation. 52. Bridged and Chiral Hemispherands”, J. Org. Chem., vol. 54, 1989, pp. 5460-5482.
Cram et al., “Host-Guest Complexation. 36. Spherand and Lithium and Sodium Ion Complexation Rates and Equilibria”, J. Am. Chem. Soc., vol. 107, 1985, pp. 3657-3668.
Cram et al., “Host-Guest Complexation. 35. Spherands, The First Completely Preorganized Liquid Systems”, J. Am. Chem. Soc., vol. 107, 1985, pp. 3645-3657.
Cram et al., “Host-Guest Complexation. 33. Search for New Chiral Hosts”, J. Org. Chem., vol. 50, 1985, pp. 1486-1946.
Cram et al., “Spherand Complexation and Decomplexation Rates with Sodium and Lithium Picrates, and Activation Parameters for Decomplexation”, J. Chem. Soc., Chem. Commun., vol. 5, 1982, pp. 301-304.
Cram et al., “A Spherand Containing an Enforced Cavity That Selectively Binds Lithium and Sodium Ions”, J.C.S. Chem. Commun., 1979, pp. 948-950.
Cornils et al. (Eds.), Applied Homogeneous Catalysis with Organometallic Compouunds, vol. 2: Developments, 2002, pp. 740-747.
Cornils et al. (Eds.), Applied Homogeneous Catalysis with Organometallic Compounds, vol. 1: Applications, 2002, pp. 213-273.
Coates, “Precise Control of Polyolefin Stereochemistry Using Single-Site Metal Catalysts”, Chem. Rev., vol. 100, 2000, pp. 1223-1252.
Chen et al., “Divalent ansa-Zirconocenes: Stereospecific Synthesis and High Activity for Propylene Polymerization”, J. Am. Chem. Soc., vol. 126, 2004, pp. 42-43.
Chen et al., “Cocatalysts for Metal-Catalyzed Olefin Polymerization: Activators, Activation Processes, and Structure-Activity Relationships”, Chem. Rev., vol. 100, 2000, pp. 1391-1434.
Chang et al., “Syntheses of New Lactones Containing Phenyl or Methyl Groups”, J. Korean Ind. & Eng. Chemistry, vol. 9, No. 6, Nov. 1998, pp. 842-845.
Carter et al., “High Activity Ethylene Timerisation Catalysts Based on Diphosphine Ligands”, Chem. Commun., 2002, pp. 858-859.
Brintzinger et al., “Stereospecific Olefin Polymerization with Chiral Metallocene Catalysts”, Angew. Chem. Int. Ed. Engl., vol. 34, 1995, pp. 1143-1170.
Bochmann et al., “Base-Free Cationic Zirconium Benzyl Complexes as Highly Active Polymerization Catalysts,” Organometallics, vol. 12, 1993, pp. 633-640.
Blaser et al., “Enantioselective Synthesis”, Appl. Homogeneous Catalysts, vol. 3, 2002, pp. 1131-1149.
Bennett et al., “Catalytic Conjugate Addition Promoted by the Cooper(1)-monothiobinaphthol System. Part 3. Comparison of Three Thiolate-based Catalytic Systems”, J. Chem. Soc., Perkins Trans., vol. 1, 1999, pp. 3127-3132.
Barron, “Alkylalumoxanes: Synthesis, Structure, and Reactivity”, Metallocene-Based Polyolefins-Preparation, Properties & Technology, Scheirs and Kaminsky (Eds.), vol. 1, 2000, pp. 33-67.
Balsells et al., “Insight into the Mechanism of the Asymmetric Addiction to Alkyl Groups to Aldehydes Catalyzed by Titanium-BINOLate Species”, J. Am. Chem. Soc., vol. 124, 2002, pp. 10336-10348.
Arrowsmith et al., “Comparison of the Polymerization of Propene by Homogeneous and Heterogeneous Metallocene/MAO-Catalysts Under Different Polymerization Conditions,” Macromol. Chem. Phvs. vol. 202. 2001.pp. 2161-2167.
Agapie et al., “Mechanistic Studies of the Ethylene Trimerization Reaction with Xhromium-Diphosphine Catalysts: Experimental Evidence for a Mechanism Involving Metalacyclic Intermediates”, J. Am. Chem. Soc., vol. 126, 2004, pp. 1304-1305.
Patent Abstracts of Japan, JP 08 134064 A, Takasago Perfumery Co. Ltd., published May 28, 1996, abstract.
Patent Abstracts of Japan, JP 08 217775 A, Takasago Perfumery Co. Ltd., published Aug. 27, 1996, abstract.
Patent Abstracts of Japan, JP 2002 280179, Canon Inc., published Sep. 27, 2002, abstract.