And Carbon Bonded Directly To The Heavy Metal Patents (Class 556/22)
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Patent number: 6403772Abstract: New metallocene compounds are described where the ligand contains at least one open-pentadienyl containing radical characterized by a cyclic or acyclic, six &pgr; electron, delocalized, five atomic center structure. These metallocenes can advantageously be used in catalyst systems for the polymerization of olefins to generate a wide variety of different polymers including HDPE, LLDPE, ethylenelpropylene/(diene) elastomers, tactiospecific C3+&agr;-olefin polymers, intimate mixture thereof and the like.Type: GrantFiled: March 6, 1998Date of Patent: June 11, 2002Assignee: Montell Technology Company, BVInventors: John A. Ewen, Robert W. Strozier, Robert L. Jones, Jr., Michael J. Elder
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Patent number: 6342621Abstract: Penta-coordinated ruthenium catalysts for the metathesis reactions of olefins, in particular ring opening metathesis polymerization (ROMP) of cyclo-olefin monomers, which are cationic complexes represented by formula I, II or III: wherein each of X1 and X2, which may be the same or different, is an optionally substituted C3-C20 hydrocarbon group having an allyl moiety as an end group bonded to the ruthenium atom, or X1 and X2 together form a group, optionally substituted, which results from dimerization of an alkene and has at each end an allyl group bonded to the ruthenium atom; L1 and L2 are mono-dentate neutral electron donor ligands, preferably highly sterically encumbered neutral electron donor ligands such as alkyl phosphines or amines; L{circumflex over ( )}L is a bidentate neutral electron donor ligand, preferably phosphine, amino, imino, arsine or arphos; L3 is a solvent molecule or a neutral mono-dentate electron donor ligand; L{circumflex over ( )}L{circumflex over ( )}L is a tridType: GrantFiled: January 27, 2000Date of Patent: January 29, 2002Assignee: Nippon Zeon Co., Ltd.Inventors: Shakti L. Mukerjee, Vernon L. Kyllingstad
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Patent number: 6342605Abstract: Bidentate phosphine ligands of the formula wherein the substituents are as defined in the specification and a process for preparing linear aldehydes by hydroformylating internal olefins using such phosphine ligands.Type: GrantFiled: August 18, 1999Date of Patent: January 29, 2002Assignee: Celanese GmbHInventors: Holger Geissler, Petrus W. N. M. van Leeuwen, Paul C. J. Kamer, Lars A. van der Veen
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Patent number: 6313331Abstract: The present invention relates to novel complexes of (transition) metals containing ligands having phosphorus centers supporting a carbene structure or heteroalkane radical bonded to the (transition) metal.Type: GrantFiled: February 25, 2000Date of Patent: November 6, 2001Assignee: The Governors of the University of AlbertaInventors: Ronald G. Cavell, Qinyan Wang, Ruppa P. Kamalesh Babu, Aparna Kasani
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Patent number: 6310121Abstract: Compositions including fibers, fillers, reinforcing agents or other property-enhancing agents added to a polymeric matrix formed from DCPD monomer or related compounds such as norbornene and norbornadiene are disclosed. The composition has a mechanically forgiving matrix due to the polymer with the inherent strength and other physical properties of the enhancement agent according to the invention. Enhancement agents according to the invention generally include inorganic, organic and metallic substances in a variety of forms.Type: GrantFiled: August 7, 1998Date of Patent: October 30, 2001Assignee: Cymetech, LLCInventors: Charles S. Woodson, Jr, Robert H. Grubbs
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Patent number: 6306988Abstract: A method for the cross-metathesis of terminal olefins is disclosed. The method describes making disubstituted internal olefin products by contacting a first terminal olefin with another first terminal olefin to form a dimer and then contacting the dimer with a second terminal olefin in the presence of a catalyst having the formula where M may be Os or Ru, R and R1 may be the same or different and may be hydrogen or a substitutent group selected from C1-C20 alkyl, C2-C20 alkenyl,C2-C20 alkynyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, aryloxy, C2-C20 alkoxycarbonyl, C1-C20 alkylthio, C1-C20 alkylsulfonyl, and C1-C20 alkylsulfinyl. X and X1 may be the same or different and may be any anionic ligand. L and L1 may be the same or different and may be any neutral electron donor.Type: GrantFiled: January 26, 2000Date of Patent: October 23, 2001Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, Daniel J. O'Leary, Helen E. Blackwell
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Patent number: 6306987Abstract: Disclosed is a compound of formula (I), and its use in preparing metathesis polymers of dicyclopentadiene and/or other strained cycloolefins in which Me is ruthenium or osmium; X1 and X2 independently of one another are anionic ligands, or X1 and X2 together are a bis-anionic ligand; Y is oxygen, sulfur or the groups —NR7— or —PR7—, where R7 is hydrogen or a substituent selected from the group C1-C6alkyl, C6-C13aralkyl, sulfonyl and —C(═O)Rs2 and Rs2 is hydrogen or a substituent selected from the group C1-C12alkyl, C2-C12alkenyl, C3-C12cycloalkyl, C3-C12cycloalkenyl, C2-C11heterocycloalkyl, C2-C11heterocycloalkenyl, C5-C12aryl, C1-C9heteroaryl, C6-C14aralkyl, C2-C13heteroaralkyl, C6-C14aralkenyl and C3-C13heteroaralkenyl; n is 0 or 1; L1 is tertiary phosphine; and L2 is a neutral e− donor ligand which is coordinated to the metal atom and is attached via the bridge group C* to the carbon atom of the carbene group if n is 0 and to Y if n is 1.Type: GrantFiled: December 16, 1999Date of Patent: October 23, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Paul Adriaan Van Der Schaaf, Andreas Hafner, Andreas Mühlebach
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Patent number: 6225488Abstract: Penta-coordinated ruthenium or osmium catalysts for metathesis reactions of olefins, which are cationic complexes represented by formulas I, II or III: wherein M is ruthenium or osmium; each of X1 and X2, which may be the same or different, is an optionally substituted C3-C20 hydrocarbon group having an allyl moiety as an end group bonded to the central metal atom M, or X1 and X2 together form a group, optionally substituted, which results from dimerization of an alkene and has at each end an allyl moiety bonded to the central metal atom M, L1 is a neutral electron donor ligand; L2 is a carbene group; L3 is a neutral electron donor ligand which may be the same as or different from L1, or L3 is a halide group; L11 is a neutral electron donor ligand; L12 is a solvent molecule capable of coordination to the central metal atom M; L13 is an alkyl group; L14 is an alkyl, a carbene, a solvent molecule capable of coordination to the central metal atom M, or a halide; L{circumflex over ( )}L is a bidType: GrantFiled: April 2, 1999Date of Patent: May 1, 2001Assignee: Nippon Zeon Co., Ltd.Inventors: Shakti L. Mukerjee, Vernon L. Kyllingstad
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Patent number: 6197716Abstract: The present invention relates to a hydrogenation process for the production of aromatic halogen-amino compounds by means of catalytic hydrogenation on noble metal catalysts of corresponding aromatic halonitro compounds, characterised in that a rhodium, ruthenium, iridium, platinum or palladium catalyst which is modified with an inorganic or organic phosphorus compound with a degree of oxidation of less than V, is used, in the presence of a vanadium compound.Type: GrantFiled: November 4, 1998Date of Patent: March 6, 2001Assignee: Novartis AGInventors: Peter Baumeister, Urs Siegrist, Martin Studer
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Patent number: 6191294Abstract: A new process is disclosed, particularly simple, convenient and practical, for the direct synthesis of metallocenes of formula (I): (CP)(ZR1m)n(A)rMLpL′q wherein (ZR1m)n is a divalent group bridging Cp and A; Cp is a substituted or unsubstituted cyclopentadieryl group; A is —O—, —S—, —N(R2)—, wherein R2 is hydrogen, alkyl, cycloalkyl aryl, alkylaryl or arylalkyl, or A has the same meaning of Cp; M is a transition metal belonging to group 3, 4, 5, 6 or to the lanthanide or actinide groups; L is a monoanionic sigma ligand, such as alkyl, cycloalkyl, aryl, alkylaryl or arylalkyl, optionally containing Si or Ge; L′ is halogen or —OR5, R5 being a hydrocarbon radical; m is 1 or 2; n is 0-4; r is 0 or 1; p is 1-3; q is 0-2.Type: GrantFiled: September 13, 1999Date of Patent: February 20, 2001Assignee: Montell Technology Company BVInventors: Luigi Resconi, Davide Balboni, Giansiro Prini
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Patent number: 6175025Abstract: A di-substituted metallocene compound having good quality can be synthesized completely at a low cost in a high yield in a easy manner by reacting a metallocene dihalide with a Grignard reagent which is a compound represented by formula (I): RMgX (wherein R represents an aryl, benzyl or diaryl phosphinomethylene group which may have a substituent and X represents a halogen element) under specified conditions.Type: GrantFiled: February 23, 2000Date of Patent: January 16, 2001Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Yuichi Kitagawa, Koji Otaka, Tomoya Kubo, Eiji Takeichi
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Patent number: 6172249Abstract: An enantiomerically enriched compound of formula (4) or the opposite enantiomer thereof, wherein R is C1-10 alkyl. This compound, in the form of a transition metal complex, is useful as a catalyst for stereoselective hydrogenation.Type: GrantFiled: November 4, 1999Date of Patent: January 9, 2001Assignee: Chirotech Technology, Ltd.Inventors: Ulrich Berens, Mark Joseph Burk, Arne Gerlach
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Patent number: 6171994Abstract: A novel multiply crosslinked transition metal compound represented by the formula (I): wherein M is a metallic element of the Groups 3 to 10 or the lanthanide series of the Periodic Table; E1 and E2 are each a &sgr;-bonding or &pgr;-bonding ligand; X is a &sgr;-bonding ligand; Y is a Lewis base; A1, A2, . . . An and D are each a crosslinking group, and at least one of A1, A2, . . . An comprises a crosslink consisting of carbon alone; n is 2 to 4; p is 1 to 4; q is 1 to 5 and equal to the valence of M minus 2; r is 0 to 3; and s is 0 to 4, and a production process thereof. The transition metal compound is useful as a component of a polymerization catalyst for catalyzing the production of an olefin polymer having a uniform composition and a narrow molecular weight distribution in a high yield.Type: GrantFiled: November 2, 1998Date of Patent: January 9, 2001Assignee: Idemitsu Kosan Co., Ltd.Inventors: Nobuhiro Yabunouchi, Kiyohiko Yokota, Masami Watanabe, Takuji Okamoto, Noriyuki Tani
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Patent number: 6169192Abstract: The invention relates to 1,2-ferrocenyldiphosphines which contain a functional group in the 1′ position either directly or via a bridging group, and also a process for their preparation. The compounds are important for transition metal complexes containing d-8 metals such as Rh, Ru, Pd or Ir. These transition metal complexes are widely used in the hydrogenation of organic double or triple bonds, in particular olefinic double bonds and carbon-heteroatom double bonds. The complexes are particularly suitable for enantioselective hydrogenation using chiral ferrocenyldiphosphines and corresponding prochiral unsaturated compounds. Ferrocenyldiphosphines having a functional group in the 1′ position are also important intermediates for ferrocenyldiphosphine ligands and their metal complexes of d-8 metals such as rhodium, ruthenium, palladium or iridium which are bound to inorganic polymeric supports via this functional group.Type: GrantFiled: January 8, 1999Date of Patent: January 2, 2001Assignee: Novartis AGInventors: Beno{circumflex over (i)}t Pugin, Heidi Landert
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Patent number: 6133464Abstract: The invention relates to chiral ferrocenyls of formula (I) ##STR1## wherein R.sub.a is --P(R.sub.10 R.sub.11) or --SR.sub.12 ;R.sub.b is --P(R'.sub.10 R'.sub.11), --SR'.sub.12, --CH.dbd.NR.sub.12, --CH.sub.2 --NH--R.sub.12 or --CH.sub.2 --O--P(R.sub.10 R.sub.11); and the other substituents are as defined in claim 1,which may be used as ligands for transition metal catalysts in enantioselective reactions.Type: GrantFiled: March 8, 1999Date of Patent: October 17, 2000Assignee: Novartis AGInventors: Benoit Pugin, Heidi Landert, Giorgio Pioda
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Patent number: 6127563Abstract: Disclosed is a process for preparing bridged Group 4 metal complexes containing a neutral diene ligand starting from the corresponding novel, metal diene containing complexes by reaction thereof with the divalent derivative of a bridged bidentate ligand compound. The novel, intermediate metal diene complexes, their formation from tetravalent metal salts and an integrated process combining both process steps are claimed.Type: GrantFiled: October 20, 1999Date of Patent: October 3, 2000Assignee: The Dow Chemical CompanyInventors: Eugene Y. Chen, David D. Devore, Richard E. Campbell, Jr., D. Patrick Green, Jasson T. Patton, Jorge Soto, David R. Wilson
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Patent number: 6096912Abstract: Abstract of the Disclosure: Catalyst systems for the polymerization of C.sub.2 -C.sub.10 -alk-1-enes contain, as active components,a) a metallocene complex of the general formula I ##STR1## where M is titanium, zirconium, hafnium, vanadium, niobium or tantalum, X is halogen or C.sub.1 -C.sub.8 -alkyl, Y is carbon, phosphorus, sulfur, silicon or germanium, Z is C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.10 -cycloalkyl or C.sub.6 -C.sub.10 -aryl, R.sup.1 and R.sup.2 are identical or different and are each C.sub.1 -C.sub.4 -alkyl, R.sup.3 to R.sup.6 are identical or different and are each hydrogen or C.sub.1 -C.sub.8 -alkyl, or two adjacent radicals R.sup.3 and R.sup.4 and R.sup.5 and R.sup.6 in each case together form a hydrocarbon ring system of 4 to 15 carbon atoms and n is 0, 1 or 2, andb) an open-chain or cyclic alumoxane compound of the general formula II or III ##STR2## where R.sup.7 is C.sub.1 -C.sub.4 -alkyl and n is from 5 to 30.Type: GrantFiled: May 3, 1996Date of Patent: August 1, 2000Assignee: BASF AktiengesellschaftInventors: Eberhard Karl, Werner Roell, Hans Brintzinger, Bernhard Rieger, Udo Stehling
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Patent number: 6090739Abstract: The present invention relates to a transition metal compound of the formula I ##STR1## where M.sup.1 is a metal of group IIIb, IVb or Vb of the Periodic Table of the Elements,R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are identical or different and are each a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.40 -hydrocarbon-containing group, an --SiR.sup.5.sub.3, --NR.sup.5.sub.2, --Si(OR.sup.5).sub.3, --Si(SR.sup.5).sub.3 or --PR.sup.5.sub.2 radical, where R.sup.5 are identical or different and are each a halogen atom, a C.sub.1 -C.sub.10 -alkyl group or a C.sub.6 -C.sub.10 -aryl group, or two or more radicals R.sup.1, R.sup.2, R.sup.3 or R.sup.4 together with the atoms connecting them form a ring system,Y are identical or different and are each a hydrogen atom, a C.sub.1 -C.sub.40 -hydrocarbon-containing group, an OH group, a halogen atom or an NR.sup.5.sub.2 group,k is an integer which corresponds to the valence of the transition metal atom M.sup.1 minus two and if Y is a butadiene unit, k is 1,A is a bridge,R.Type: GrantFiled: June 18, 1997Date of Patent: July 18, 2000Assignee: Targor GmbHInventors: Michael Riedel, Gerhard Erker, Lothar Duda
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Patent number: 6084115Abstract: Disclosed is a process for preparing bridged Group 4 metal complexes containing a neutral diene ligand starting from the corresponding novel, metal diene containing complexes by reaction thereof with the divalent derivative of a bridged bidentate ligand compound. The novel, intermediate metal diene complexes, their formation from tetravalent metal salts and an integrated process combining both process steps are claimed.Type: GrantFiled: March 10, 1999Date of Patent: July 4, 2000Assignee: The Dow Chemical CompanyInventors: Eugene Y. Chen, Richard E. Campbell, Jr., David D. Devore, D. Patrick Green, Jasson T. Patton, Jorge Soto, David R. Wilson
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Patent number: 6084114Abstract: The invention relates to palladaphosphacyclobutanes of the formula (I) ##STR1## where R.sup.1, R.sup.2 are, independently of one another, hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.3 -C.sub.12)-cycloalkyl, (C.sub.1 -C.sub.4)-alkoxy, fluorine, N[(C.sub.1 -C.sub.4)-alkyl].sub.2, CO.sub.2 -(C.sub.1 -C.sub.4)-alkyl, OCO-(C.sub.1 -C.sub.4)-alkyl or aryl;R.sup.3, R.sup.4, R.sup.5, R.sup.6 are, independently of one another, (C.sub.1 -C.sub.8)-alkyl, (C.sub.3 -C.sub.12)-cycloalkyl or aryl;or where R.sup.1 and R.sup.2, R.sup.1 or R.sup.2 and R.sup.3 or R.sup.4, R.sup.3 and R.sup.4, R.sup.3 or R.sup.4 and R.sup.5 or R.sup.6, or R.sup.5 and R.sup.6 together form an aliphatic ring; or where R.sup.5 and R.sup.6, R.sup.3 or R.sup.4 and R.sup.5 or R.sup.6 together form an aromatic ring; andY is an anion of an inorganic or organic acid, with the exception of the compoundsdi-.mu.-chloro-bis[2-[bis(1,1-dimethylethyl)phosphino]-2-methylpropyl-C,P]d ipalladium(II)di-.mu.Type: GrantFiled: July 19, 1999Date of Patent: July 4, 2000Assignee: Aventis Research & Technologies GmbH & Co. KGInventors: Holger Geissler, Peter Gross, Bianca Guckes
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Patent number: 6077805Abstract: Hexacoordinated ruthenium and osmium catalysts of the formulae ##STR1## in which M and M' independently of one another are ruthenium or osmium;X, X', Y and Y' independently of one another are anionic ligands, or X and Y and X' and Y' in each case together are bis-anionic ligandsL.sup.1 and L.sup.1' independently of one another are tertiary phosphine;L.sup.2 and L.sup.3 independently of one another are a monodentate ligand, or L.sup.2 and L.sup.3 together are bidentate, neutral electron donor ligands;L.sup.4 is tetradentate, neutral electron donor ligand;L.sup.5 is a bidentate, neutral electron donor ligand; andT and T' indepedently of one another are H or organic substituents, are useful for the synthesis of custom-tailored polymers and for the ring-closing metathesis of olefins.Type: GrantFiled: March 2, 1998Date of Patent: June 20, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Paul Adriaan Van Der Schaaf, Andreas Hafner, Andreas Muhlebach
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Patent number: 6069264Abstract: The present invention relates to a transition metal compound of the formula I ##STR1## where M.sup.1 is a transition metal of group IIIb, IVb, Vb or VIb of the Periodic Table of the Elements,Y are identical or different and are each a hydrogen atom, an OH group, a halogen atom, a C.sub.1 -C.sub.40 -hydrocarbon-containing group or an NR.sup.15.sub.2 group, where R.sup.15 is a halogen atom, a C.sub.1 -C.sub.10 -alkyl group or a C.sub.6 -C.sub.10 -aryl group, k is an integer which corresponds to the valence of the transition metal atom M.sup.1 minus two and, if Y is a butadiene unit, k is 1,R.sup.1, R.sup.2, R.sup.3, R.sup.7, R.sup.8 and R.sup.9 are identical or different and are each a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.40 -hydrocarbon-containing group, an --SiR.sup.15.sub.3, --NR.sup.15.sub.2, --SiOR.sup.15.sub.3, --SiSR.sup.15.sub.3 or --PR.sup.15.sub.2 radical, where R.sup.15 is a halogen atom, a C.sub.1 -C.sub.10 -alkyl group or a C.sub.6 -C.sub.Type: GrantFiled: June 12, 1997Date of Patent: May 30, 2000Assignee: Targor GmbHInventors: Michael Riedel, Gerhard Erker, Martin Konnemann
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Patent number: 6069237Abstract: New metallocene ligand systems and catalysts/catalyst precursors are described where the ligand system contains at least one open-pentadienyl ligand characterized by an acyclic six .pi. electron delocalized, five atomic center structure. The open pentadienyl ligand is bonded to either another pentadienyl ligand or a Cp ligand by a bridging group. The metal is from group 3-5 or the Lanthanides. These metallocene catalysts/catalyst precursors optionally in combination with co-catalysts can be used to generate a wide variety of different polymer types including HDPE, LLDPE, LHDPE, ethylene/propylene elastomers, tactiospecific C3+ .alpha.-olefins, intimate mixture thereof and the like.Type: GrantFiled: September 11, 1995Date of Patent: May 30, 2000Assignee: Montell Technology Company BVInventors: John A. Ewen, Robert W. Strozier
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Patent number: 6060568Abstract: The present invention relates to novel complexes of (transition) metals containing ligands having phosphorus centers supporting a carbene structure or heteroalkane radical bonded to the (transition) metal.Type: GrantFiled: August 19, 1999Date of Patent: May 9, 2000Assignee: The Governors of the University of AlbertaInventors: Ronald G. Cavell, Qinyan Wang, Ruppa P. Kamalesh Babu, Aparna Kasani
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Patent number: 6057466Abstract: Compounds, for initiating the polymerization of ethylenically unsaturated compounds, having the formula ##STR1## where E is nitrogen, phosphorus, arsenic or antimony,X is oxygen, NR.sup.1 or sulphur,L is R.sup.8 R.sup.9 R.sup.10 E.sup.1 (Y).sub.n, alkyl ether, ester, alkyl and aryl nitrites, pyridine, piperidine, sulphoxides, sulphones, sulphimides, sulphodiimides or sulphur ylides, and R.sup.1 -R.sup.5 are as defined in the specification.Type: GrantFiled: September 29, 1997Date of Patent: May 2, 2000Assignee: Bayer AktiengesellschaftInventors: Karl-Heinz Aleksander Ostoja Starzewski, Uwe Denninger
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Patent number: 6051727Abstract: A very effective catalyst system for the polymerization or copolymerization of olefins comprises a cocatalyst, preferably an aluminoxane or a supported aluminoxane, and a metallocene of the formula I ##STR1## in which, in the preferred form, M.sup.1 in Zr or Hf, R.sup.1 and R.sup.2 are halogen or alkyl, R.sup.3 is alkyl, R.sup.4 to R.sup.12 are alkyl or hydrogen and R.sup.13 is a (substituted) alkylene or heteroatom bridge. The metallocenes, in particular the zirconocenes, produce polymers of very high molecular weight, in the case of prochiral monomers polymers of very high molecular weight, very high stereotacticity and very high melting point, at high catalyst activities in the industrially particularly interesting temperature range between 50 and 80.degree. C. In addition, reactor deposits are avoided by means of supported catalyst systems.Type: GrantFiled: December 31, 1997Date of Patent: April 18, 2000Assignee: Targor GmbHInventors: Frank Kuber, Bernd Bachmann, Walter Spaleck, Andreas Winter, Jurgen Rohrmann
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Patent number: 6043387Abstract: New chiral biphosphines, e.g., ##STR1## are useful as key components in catalysts for asymmetric reactions, providing desirably high enantiomeric excess (ee).Type: GrantFiled: February 3, 1999Date of Patent: March 28, 2000Assignee: Merck & Co., Inc.Inventors: Philip Pye, Ralph P. Volante, Kai Rossen
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Patent number: 6013819Abstract: Metal complexes having constrained geometry and a process for preparation thereof, addition polymerization catalysts formed therefrom, processes for preparation of such addition polymerization catalysts, methods of use, and novel polymers formed thereby, including ElPE resins and pseudo-random copolymers, are disclosed and claimed.Type: GrantFiled: August 26, 1996Date of Patent: January 11, 2000Assignee: The Dow Chemical CompanyInventors: James C. Stevens, Robert K. Rosen
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Patent number: 5990331Abstract: The present invention relates to a metallocene of the formula I, ##STR1## for preparing polyolefins, where M.sup.1 is preferably Zr, Hf or Ti, R.sup.1 and R.sup.2 are each a hydrogen atom, a C.sub.1 -C.sub.3 -alkyl group, a C.sub.1 -C.sub.3 -alkoxy group, a C.sub.6 -C.sub.8 -aryl group, a C.sub.6 -C.sub.8 -aryloxy group, a C.sub.2 -C.sub.4 -alkenyl group, a C.sub.7 -C.sub.10 -arylalkyl group, a C.sub.7 -C.sub.12 -alkylaryl group, a C.sub.8 -C.sub.12 -arylalkenyl group or chlorine, R.sup.3 is a chlorine atom, a C.sub.1 -C.sub.3 -alkyl group, a C.sub.2 -C.sub.4 -alkenyl group, a C.sub.6 -C.sub.8 -aryl group, an NR.sup.16.sub.2, SR.sup.16, OSiR.sup.16.sub.3, SiR.sup.16.sub.3 or PR.sup.16.sub.2 radical where R.sup.16 is chlorine, a C.sub.1 -C.sub.4 -alkyl group or a C.sub.6 -C.sub.8 -aryl group. R.sup.4 is a hydrogen atom, R.sup.13 is --(R.sup.14 M.sup.2 R.sup.15)--, --(R.sup.14 CR.sup.15)--(R.sup.14 CR.sup.15)--, --(R.sup.14 CR.sup.15)--(R.sup.14 M.sup.2 R.sup.15)-- or --(R.sup.14 CR.sup.15)--, where R.sup.Type: GrantFiled: October 31, 1997Date of Patent: November 23, 1999Assignee: Targor GmbHInventors: Andreas Winter, Roland Zenk, Volker Fraaije, Frank Kuber
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Patent number: 5969170Abstract: Disclosed are ruthenium and osmium carbene compounds which are stable in the presence of a variety of functional groups and which can be used to catalyze olefin metathesis reactions on strained and unstrained cyclic and acyclic olefins. Specifically, the present invention relates to carbene compounds of the formula ##STR1## wherein: M is Os or Ru; R and R.sup.1 are independently selected from hydrogen and substituent groups C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.2 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl or C.sub.1 -C.sub.20 alkylsulfinyl; each substituent group optionally substituted with C.sub.1 -C.sub.5 alkyl, a halogen, C.sub.1 -C.sub.5 alkoxy or with a phenyl group optionally substituted with a halogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy; X and X.sup.Type: GrantFiled: May 23, 1997Date of Patent: October 19, 1999Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, SonBinh T. Nguyen, Lynda K. Johnson
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Patent number: 5965758Abstract: A method for producing a bridged type transition metal complex represented by the following formula (1), comprising the following steps (i) and (ii):step (i); a step for reacting a specific cyclopentadiene compound with an organic alkaline metal compound or an organomagnesium compound to produce an alkaline metal salt compound or a magnesium salt compound of the cyclopentadiene compound; andstep (ii); a step for reacting the alkaline metal salt compound or magnesium salt compound of the cyclopentadiene compound with a specific transition metal compound, wherein at least the step (ii) is performed in the presence of an amine compound.According to the present invention, there can be provided a method for producing a bridged type transition metal complex having one cyclopentadiene type anion skeleton on an industrial scale in high yield without requiring an industrially disadvantageous low temperature and replacement of the solvent, which is capable of reducing the number of the steps.Type: GrantFiled: June 18, 1998Date of Patent: October 12, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Masaaki Nabika, Kotohiro Nomura
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Patent number: 5965756Abstract: Group 4 metal constrained geometry complexes comprising a fused ring indenyl derivative ligand, catalytic derivatives thereof, processes for preparing the same and their use as components of olefin polymerization catalysts are disclosed.Type: GrantFiled: October 14, 1997Date of Patent: October 12, 1999Assignee: The Dow Chemical CompanyInventors: Mark H. McAdon, Jasson T. Patton, Peter N. Nickias, Ravi B. Shankar, Francis J. Timmers, Brian W. Kolthammer, Daniel D. VanderLende, Steven M. Ueligger
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Patent number: 5939504Abstract: Compositions and methods for catalyzing and controlling the rate of olefin metathesis reactions including Ring Opening Metathesis Polymerization (ROMP) reactions. The molding of polymer articles using ROMP polymers. The composition includes a Ruthenium or Osmium carbene complex catalyst and a gel modification additive. The Ruthenium or Osmium carbene complex catalyst having the formula ##STR1## where M may be Os or Ru; R and R.sup.1 may be the same or different and may be hydrogen or a substituent group including C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.1 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl and C.sub.1 -C.sub.20 alkylsulfinyl; X and X.sup.1 may be the same or different and may be any anionic ligand; and L and L.sup.1 may be the same or different and may be neutral electron donor.Type: GrantFiled: December 2, 1996Date of Patent: August 17, 1999Assignee: Advanced Polymer TechnologiesInventors: Charles S. Woodson, Jr., Robert H. Grubbs
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Patent number: 5919961Abstract: Chiral compounds of the formula I ##STR1## where the variables are as described in the specification.Type: GrantFiled: May 30, 1997Date of Patent: July 6, 1999Assignee: BASF AktiengesellschaftInventors: Rainer Sturmer, Jun Okuda, Kurt Ritter
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Patent number: 5912310Abstract: Metallocene complexes of the formula I ##STR1## where M is titanium, zirconium, hafnium, vanadium, niobium or tantalum,n is an integer from 0 to 10,R.sup.5 is ##STR2## R.sup.11 to R.sup.14 are as designated in the disclosure, n.sup.1 is an integer from 0 to 10,X.sup.1 to X.sup.4 are each fluorine, chlorine, bromine, iodine, hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.15 -aryl, alkylaryl having 1 to 10 carbon atoms in the alkyl radical and 6 to 20 carbon atoms in the aryl radical, --OR.sup.15 --, --NR.sup.15 R.sup.16 or ##STR3## R.sup.15 to R.sup.21 are as designated in the disclosure, and o, p, q, r are each an integer from 0 to 4, the sum o+p+q+r+1 corresponding to the valency of M,which were used as active catalyst components in the preparation of polymers of C.sub.2 -C.sub.10 -alkenes, are recovered by a process wherein the polymerization is stopped by adding an acid and the metallocene complexes of the formula I are recovered by extraction from the reaction mixture.Type: GrantFiled: March 23, 1998Date of Patent: June 15, 1999Assignee: BASF AktiengesellschaftInventors: Marc Oliver Kristen, Peter Jutzi, Thomas Redeker
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Patent number: 5912376Abstract: A process for the preparation of a metal carbene, in which a metal salt is first reacted in the presence of a base and a secondary or tertiary alcohol with a tertiary phosphine or phosphite or a ditertiary diphosphine or diphosphite and then reacted in the presence of an acid with an alkyne and, if desired, an alkene.Type: GrantFiled: October 27, 1997Date of Patent: June 15, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Paul Adriaan Van Der Schaaf, Roman Kolly, Andreas Hafner, Andreas Muhlebach
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Patent number: 5883277Abstract: Metallocene complexes having a cationic bridge of the formula ##STR1## where the substituents have the following meanings: M is a metal of transition group III, IV, V or VI of the Periodic Table of the Elements or a metal of the lanthanide group,X is fluorine, chlorine, bromine, iodine, hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.15 -aryl or --OR.sup.5,R.sup.1 to R.sup.12, Y, Z and n having the meanings set out in the specification, said complexes can be prepared via ligand systems of the formula II ##STR2## as intermediates.Type: GrantFiled: August 14, 1997Date of Patent: March 16, 1999Assignee: BASF AktiengesellschaftInventors: David Fischer, Franz Langhauser, Gunther Schweier, Hans-Herbert Brintzinger, Nadine Leyser
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Patent number: 5883275Abstract: The present invention relates to a process for the hydrogenation of metallocenes, which comprises treating at least one metallocene containing at least one double bond and/or at least one aromatic substituent in at least one nonhalogenated solvent with hydrogen in the presence of at least one hydrogenation catalyst.Type: GrantFiled: October 31, 1997Date of Patent: March 16, 1999Assignee: Targor GmbHInventors: Carsten Bingel, Erich Hubscher, Claus-Peter Niesert, Roland Zenk
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Patent number: 5856540Abstract: The present invention relates to optically active and racemic C.sub.2 -symmetric 2,2'-disubstituted 1,1'-diphosphino-ferrocenes of the formula Ia, to optically active and racemic asymmetric 1',2-disubstituted 1-phosphino-ferrocenes of the formula Ib and to achiral 2,2'-disubstituted 1,1'-diphosphino-ferrocenes of the formula II, to processes for preparing them, especially in accordance with the principle of asymmetric ortho-lithiation, to their use as ligands for transition metal complexes, to transition metal complexes comprising them, and to the use of the transition metal complexes as catalysts, especially in asymmetric syntheses.Type: GrantFiled: April 24, 1997Date of Patent: January 5, 1999Assignee: Hoechst AktiengesellschaftInventor: Joachim-Heiner Jendralla
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Patent number: 5831107Abstract: A palladacycle of the formula (I) ##STR1## where: R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are, independently of one another, hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy, fluorine, NH.sub.2, NH-alkyl(C.sub.1 -C.sub.4), N(alkyl).sub.2 -(C.sub.1 -C.sub.4), CO.sub.2 -(C.sub.1 -C.sub.4)alkyl, OCO-alkyl-(C.sub.1 -C.sub.4), or phenyl,R.sup.7 and R.sup.8 are, independently of one another, (C.sub.1 -C.sub.8)-alkyl, (C.sub.3 -C.sub.12)-cyloalkyl, substituted or unsubstituted arylor where R.sup.1, and R.sup.2, R.sup.2 and R.sup.3, R.sup.3 and R.sup.4, R.sup.5 and R.sup.6 together form an aliphatic or aromatic ring, andY is an anion of an inorganic or organic acid.Type: GrantFiled: December 10, 1996Date of Patent: November 3, 1998Assignee: Aventis Research & Technology DeutschlandInventors: Matthias Beller, Hartmut Fischer, Wolfgang Anton Herrmann, Christoph Brossmer
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Patent number: 5808121Abstract: There is disclosed a catalyst composition prepared by reacting together:(a) a source of a Group VIII metal,(b) a compound of the formula (I)R.sup.1 R.sup.2 PR.sup.4 CO.sub.2 R.sup.3 (I)where R.sup.1 and R.sup.2 are independently an unsubstituted or substituted alkyl, cycloalkyl or aryl group, R.sup.3 is hydrogen, an unsubstituted or substituted alkyl, cycloalkyl or aryl group and R.sup.4 is a divalent organic group and(c) a source of an anion which is either non-coordinating or weakly-coordinating to the Group VIII metal.The catalyst compositions are used in the preparation of polyketones from carbon monoxide and one or more olefins. Novel compounds of the formula ?(.eta..sup.3 -allyl)Pd(R.sub.1 R.sup.2 PR.sup.4 CO.sub.2 R.sup.3)!A where A is a weakly or non-coordinating anion are useful as such catalysts.Type: GrantFiled: February 12, 1996Date of Patent: September 15, 1998Assignee: BP Chemicals LimitedInventors: Wilhelm Keim, Stefan Mecking
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Patent number: 5780701Abstract: An improved process is described for the catalytic dehydrogenation of organic molecules having a ##STR1## group to produce a ##STR2## group. The organic molecules are: ##STR3## wherein: A.sup.1, A.sup.2, A.sup.3, and A.sup.4 are each independently P, As or N: E.sup.2 is independently C or N; E.sup.3 is independently C, Si or Ge; E.sup.4 is independently C, Si, or Ge; and E.sup.5 is independently C, Si or Ge; M.sup.1, M.sup.2, M.sup.3, and M.sup.4 each is a metal atom independently selected from the group consisting of ruthenium, rhodium, palladium, osmium, iridium and platinum; Q.sup.1, Q.sup.2, Q.sup.3, and Q.sup.4 are each independently a direct bond, --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, or CH.dbd.CH--;in structure I, structure II or structure IV, R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are each independently selected from alkyl, alkenyl, cycloalkyl, and aryl, or R.sup.1 and R.sup.2 together and R.sup.3 and R.sup.4 together form a ring structure having from 4 to 10 carbon atoms, orin structure III, R.sup.Type: GrantFiled: July 26, 1996Date of Patent: July 14, 1998Assignees: The Regents of the University of California, University of HawaiiInventors: William C. Kaska, Craig M. Jensen
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Patent number: 5770753Abstract: Metallocenes containing aryl-substituted indenyl derivatives as ligands, process for their preparation, and their use as catalysts.A very effective catalyst system for the polymerization or copolymerization of olefins comprises a cocatalyst, preferably an aluminoxane or a supported aluminoxane, and a metallocene of the formula I ##STR1## in which, in the preferred form, M.sup.1 is Zr or Hf, R.sup.1 and R.sup.2 are halogen or alkyl, R.sup.3 is alkyl, R.sup.4 to R.sup.12 are alkyl or hydrogen and R.sup.13 is a (substituted) alkylene or heteroatom bridge.The metallocenes, in particular the zirconocenes, produce polymers of very high molecular weight, in the case of prochiral monomers polymers of very high molecular weight, very high stereotacticity and very high melting point, at high catalyst activities in the industrially particularly interesting temperature range between 50.degree. and 80.degree. C. In addition, reactor deposits are avoided by means of supported catalyst systems.Type: GrantFiled: June 7, 1995Date of Patent: June 23, 1998Assignee: Targor GmbHInventors: Frank Kuber, Bernd Bachmann, Walter Spaleck, Andreas Winter, Jurgen Rohrmann
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Patent number: 5760264Abstract: Disclosed is a novel method of producing optically active metallocenyl phosphines of the general formula shown In the formula (Ia) (Ib), M represents iron, ruthenium or nickel; R.sup.1 and R.sup.1' both represent C.sub.1 -C.sub.4 alkyl groups; R.sup.2 and R.sup.3 each represent independently of each other either hydrogen or a C.sub.1 -C.sub.4 alkyl group, or, together with the nitrogen atom, form a five- or six member saturated heterocyclic ring which may optionally contain further heteroatoms; R.sup.4 and R.sup.5 each represent independently of each other a C.sub.1 -C.sub.4 alkyl group (for example) or an aryl group which is optionally substituted with one or more methyl or methoxy groups or with one or more fluorine atoms.Type: GrantFiled: July 9, 1997Date of Patent: June 2, 1998Assignee: Lonza, AGInventor: Walter Brieden
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Patent number: 5750752Abstract: The present invention relates to a stereorigid transition metal compound having as ligands a cyclopentadienyl group and a substituted or unsubstituted heteroatom which are connected to one another via a monocyclic or polycyclic ring system, with the cyclopentadienyl group being fused onto the monocyclic or polycyclic ring system. The transition metal compound of the invention is suitable as a catalyst component for olefin polymerization.Type: GrantFiled: June 21, 1996Date of Patent: May 12, 1998Assignee: Hoechst AktiengesellschaftInventors: Michael Riedel, Frank Kuber, Michael Aulbach, Gerhard Erker, Martin Konemann
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Patent number: 5726115Abstract: A catalyst composition comprising a bis-amide compound represented by the formula ##STR1## wherein M is zirconium, hafnium or titanium; each N is a three coordinate nitrogen atom; each e is Si, Ge or Sn; each Z is, independently, a hydride or R; each R is, independently, a hydrocarbyl one or more carbon atoms of which may be substituted by an element selected from Si, O, P, N and S; L is a neutral Lewis base and m is a number from 0 to 2; or a dimer thereof and a second component. Preferably the second component is a compound which is capable of providing a bulky and labile anion ?A!.sup.-, which anion is substantially non-coordinating under the reaction conditions and contains at least one boron atom. Also provided is a process for oligomerizing or co-oligomerizing alpha olefins in the presence of this catalyst composition.Type: GrantFiled: March 11, 1996Date of Patent: March 10, 1998Assignee: Shell Oil CompanyInventors: Andrew David Horton, Jan De With
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Patent number: 5710298Abstract: Methods of preparing carbene compounds of the formula ##STR1## are disclosed wherein M is Os or Ru; R and R.sup.1 are independently selected from hydrogen and a functional group selected from the group consisting of C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.2 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl or C.sub.1 -C.sub.20 alkylsulfinyl; each optionally substituted with C.sub.1 -C.sub.5 alkyl, a halogen, C.sub.1 -C.sub.5 alkoxy or with a phenyl group optionally substituted with a halogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy; X and X.sup.1 are independently selected from any anionic ligand; and L and L.sup.Type: GrantFiled: August 30, 1996Date of Patent: January 20, 1998Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, SonBinh T. Nguyen, Lynda K. Johnson
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Patent number: RE37208Abstract: The novel metallocenes of the formula I in which, preferably, M1 is Zr or Hf, R1 and R2 are alkyl or halogen, R3 and R4 are hydrogen, R5 and R6 are alkyl or haloalkyl, —(CR8R9)m—R7—(CR8R9)n— is a single- or multi-membered chain in which R7 may also be a (substituted) hetero atom, m+n is zero or 1, and R10 is hydrogen, form, together with aluminoxanes as cocatalysts, a very effective catalyst system for the preparation of polyolefins or high stereospecificity and high melting point. Polyolefins with unique or improved properties are obtained by polymerizing an olefin in the presence of a metallocene combined with a cocatalyst, wherein the metallocene is preferably a zirconocene or a hafnocene, and the Zr or Hf central atom is coordinated with two ligands which are derivatives of 2-substituted indenyl nuclei and which are substituted with at least one and up to four groups (e.g. aliphatic or aromatic groups) on the six-member rings of the indenyl nuclei.Type: GrantFiled: October 17, 1994Date of Patent: June 5, 2001Assignee: Targor GmbHInventors: Andreas Winter, Martin Antberg, Walter Spaleck, Jürgen Rohrmann, Volker Dolle
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Patent number: RE37344Abstract: Compounds of formula I wherein R1 is C1-C8alkyl, phenyl or phenyl which is substituted by 1 to 3 C1-C4alkyl or C1-C4alkoxy groups; R2 and R3 are identical and are C1-C12alkyl, C5-C12cycloalkyl or C1-C4alkyl- or C1-C4alkoxy-substituted C5-C12cycloalkyl, or phenyl which is substituted by one to three identical or different members selected from the group consisting of C1-C4alkyl, C1-C4alkoxy, —SiR4R5R6, halogen, —SO3M, —CO2M, —PO3M, —NR7R8 and —[⊕NR7R8R9]X⊖; or R2 and R3 are different and are C1-C12alkyl, C5-C12cycloalkyl, C1-C4alkyl- or C1-C4-alkoxy-substituted C5-C12cycloalkyl, phenyl or phenyl which is substituted by one to three identical or different members selected from the group consisting of C1-C4alkyl, C1-C4alkoxy, —SiR4R5R6, halogen, —SO3M, —CO2M, —PO3M2, —NR7R8 and —[⊕NR7R8R9]X⊖; or the group —PR2R3 is a radical of formula II and R4, R5 and RType: GrantFiled: May 18, 2000Date of Patent: August 28, 2001Assignee: Novartis CorporationInventors: Antonio Togni, Felix Spindler, Nadia Zanetti, Amina Tijani
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Patent number: RE37384Abstract: The novel metallocenes of the formula I in which, preferably, M1 is Zr or Hf, R1 and R2 are alkyl or halogen, R3 and R4 are hydrogen, R5 and R6 are alkyl or haloalkyl, —(CR8R9)m—R7—(CR8R9)n— is a single- or multi-membered chain in which R7 may also be a (substituted) hetero atom, and m+n is zero or 1, form, together with aluminoxanes as cocatalysts, a very effective catalyst system for the preparation of polyolefins of high molecular weight.Type: GrantFiled: July 13, 1999Date of Patent: September 18, 2001Assignee: Targor GmbHInventors: Andreas Winter, Martin Antberg, Walter Spaleck, Jürgen Rohrmann, Volker Dolle