Carbon Bonded Directly To The Metal Patents (Class 556/112)
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Patent number: 6599587Abstract: Disclosed is an organometallic precursor for forming a metal pattern, having a structure defined by the following Formula 1, and a method of forming the metal pattern using the same, in which the conductive metal pattern is readily formed through an exposing step without using a photo-resist.Type: GrantFiled: September 11, 2002Date of Patent: July 29, 2003Assignee: Samsung Eleectronics Co., Ltd.Inventors: Min Chul Chung, Soon Taik Hwang, Young Hun Byun, Euk Che Hwang
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Patent number: 6589329Abstract: Compositions useful for chemical vapor delivery (CVD) formation of copper layers in semiconductor integrated circuits, e.g., interconnect metallization in semiconductor device structures, as an adhesive seed layer for plating, for the deposition of a thin-film recording head or for circuitization of packaging components. The copper precursor formulation may include one or more copper precursors, e.g., a precursor of the formula hfac(Cu)L where L is a low-cost ligand such as an alkene and/or alkyne such as [(hfac)Cu]2 (DMDVS). The formulation may include in addition to the copper precursor(s) one or more low-cost ligand species such as alkenes, alkynes, dienes and combinations thereof, to increase thermal stability of the formulation and provide enhanced vaporization properties for CVD.Type: GrantFiled: March 9, 2000Date of Patent: July 8, 2003Assignee: Advanced Technology Materials, Inc.Inventors: Thomas H. Baum, Chongying Xu
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Patent number: 6548712Abstract: The invention relates to a process for producing 1,1,1,5,5,5-hexafluoroacetylacetone. This process includes (a) hydrolyzing a metal complex of 1,1,1,5,5,5-hexafluoroacetylacetone into a 1,1,1,5,5,5-hexafluoroacetylacetone hydrate; and (b) dehydrating the hydrate into the 1,1,1,5,5,5-hexafluoroacetylacetone with high purity from a material containing a metal complex of 1,1,1,5,5,5-hexafluoroacetylacetone.Type: GrantFiled: March 15, 2001Date of Patent: April 15, 2003Assignee: Central Glass Company, LimitedInventors: Takeo Komata, Nariaki II
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Patent number: 6534666Abstract: This invention relates to an improvement in a purification process for producing those liquid copper based complexes of &bgr;-diketones and, particularly the monovalent copper complexes of &bgr;-diketones, which are suited for application by chemical vapor deposition in the electronics industry. In the basic process for preparing a copper based complex, a reactive copper compound is reacted with a fluorinated &bgr;-diketonate and an organo source such as an olefinic source or one having acetylenic unsaturation. Purification is effected by contacting reaction product with a double deionized deoxygenated water source and preferably an acid/water source. An aqueous layer and an organic layer are formed with the aqueous layer containing byproducts and the organic phase containing product.Type: GrantFiled: December 27, 2001Date of Patent: March 18, 2003Assignee: Air Products and Chemicals, Inc.Inventors: Robert Sam Zorich, James Richard Thurmond, David Allen Roberts
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Patent number: 6534665Abstract: The present invention relates to metallocenes, wherein the two cyclopentadienyl rings are connected to each other by a single carbon atom characterized by the following general formula III where each A, equal to or different from each other, is selected from the group consisting of: hydrogen, OR3, NRR4, or SR5; and to compounds of formula IV wherein each B, equal to or different from each other, is selected from the group consisting of: OH, NRH or SH, obtained by hydrolizing the corresponding oxygen, nitrogen or sulfur containing groups from compounds of formula III. These compounds are used as active catalyst components in the polymerization of olefins.Type: GrantFiled: October 26, 1999Date of Patent: March 18, 2003Assignee: Repsol Quimica S.A.Inventors: Maria Francisca Martinez Nu{overscore (n)}ez, Antonio Mu{overscore (n)}oz-Escalona LaFuente, Bego{overscore (n)}a Pe{overscore (n)}a Garcia, Pilar LaFuente Ca{overscore (n)}as
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Patent number: 6517795Abstract: A process for producing high-purity hydrotalcites by reacting alcohols or alcohol mixtures with at least one or more divalent metal(s) and at least one or more trivalent metal(s) and hydrolyzing the resultant alcoholate mixture with water. The corresponding metal oxides can be produced by calcination.Type: GrantFiled: July 31, 1997Date of Patent: February 11, 2003Assignee: Sasol Germany GmbHInventors: Klaus Noweck, Klaus Diblitz, Jan Sohiefler, Andrea Brasch
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Patent number: 6376629Abstract: A single-site olefin polymerization catalyst and method of making it are disclosed. The catalyst comprises an activator and an organometallic complex. The complex comprises a Group 3 to 10 transition or lanthanide metal, M, and at least one indenoindolyl ligand that is &pgr;-bonded to M. The key ligand is made in two steps from readily available indanones and aryl hydrazines. Reaction of its anion with a source of the metal completes a remarkably simple synthetic route to a new family of single-site olefin polymerization catalysts.Type: GrantFiled: January 29, 2001Date of Patent: April 23, 2002Assignee: Equistar Chemicals, LPInventors: Sandor Nagy, Bradley P. Etherton, Ramesh Krishnamurti, John A. Tyrell
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Patent number: 6337148Abstract: Copper precursors useful in liquid delivery CVD for forming a copper-containing material on a substrate. The disclosed copper precursors are particularly useful for metallization of interconnections in semiconductor device structures.Type: GrantFiled: May 25, 1999Date of Patent: January 8, 2002Assignee: Advanced Technology Materials, Inc.Inventors: Chongying Xu, Thomas H. Baum
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Patent number: 6316652Abstract: The invention relates to novel targeting drug agents that are targeted for entry into the mitochondria. More specifically, the agents are cisplatin derivatives called mitoplatins which are useful as anti-tumor agents. Mitoplatins are named for their targeting to the mitochondrial DNA via the carnitine-acylcarnitine translocase system. The invention also relates to methods of synthesizing mitoplatins, compositions of matter containing mitoplatins and methods of using the mitoplatins.Type: GrantFiled: June 6, 1995Date of Patent: November 13, 2001Inventor: Kosta Steliou
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Patent number: 6281377Abstract: A method of forming a volatile copper precursor for chemical vapor deposition of copper metal thin film includes formation of a volatile liquid having a chemical formula of (n-R-m-cyclohexene)Cu(I)(hfac) or (n-R-m-cyclopentene)Cu(I)(hfac), where n,m=1-6, and where R is a alkyl, such as methyl and ethyl.Type: GrantFiled: February 11, 2000Date of Patent: August 28, 2001Assignee: Sharp Laboratories of America, Inc.Inventors: Wei-Wei Zhuang, Tue Nguyen, Lawrence J. Charneski, David R. Evans, Sheng Teng Hsu
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Patent number: 6273951Abstract: Methods of forming a layer on a substrate using complexes of Formula I. The complexes and methods are particularly suitable for the preparation of semiconductor structures. The complexes are of the formula LyMYz (Formula I) wherein: M is a metal; each L group is independently a neutral ligand containing one or more Lewis-base donor atoms; each Y group is independently an anionic ligand; y=a nonzero integer; and z=a nonzero integer corresponding to the valence state of the metal.Type: GrantFiled: June 16, 1999Date of Patent: August 14, 2001Assignee: Micron Technology, Inc.Inventor: Brian A. Vaartstra
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Patent number: 6252099Abstract: A process is disclosed for increasing the fluorine content of an olefinic compound of the formula CnHmF2n−m, where n is an integer from 2 to 6 and m is an integer from 1 to 2n. The process involves (a) contacting the olefinic compound with a metal fluoride composition of the formula (AgF)(MF2)x where M is selected from the group consisting of Mn, Fe, Co, Ni, Cu, Zn and mixtures thereof and x is a number from 0 to 1, at a temperature above 200° C. sufficient to transfer F from the metal fluoride composition to the olefinic compound, thereby producing a chemically reduced metal fluoride composition comprising metallic silver; (b) oxidizing the reduced metal fluoride composition from (a) in the presence of HF to regenerate the metal fluoride composition of the formula ((AgF)(MF2)x; and (c) recycling regenerated metal fluoride composition of (b) to (a).Type: GrantFiled: March 27, 2000Date of Patent: June 26, 2001Assignee: E. I. du Pont de Nemours and CompanyInventor: Munirpallam A. Subramanian
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Patent number: 6180764Abstract: A process for producing high-purity hydrotalcites by reacting alcohols or alcohol mixtures with at least one or more divalent metal(s) and at least one or more trivalent metal(s) and hydrolysing the resultant alcoholate mixture with water. The corresponding metal oxides can be produced by calcination.Type: GrantFiled: April 30, 1999Date of Patent: January 30, 2001Assignee: RWE-DEA Aktiengesellschaft fur Mineraloel und ChemieInventors: Klaus Noweck, Klaus Diblitz, Jan Sohiefler, Andrea Brasch
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Patent number: 6150545Abstract: The present invention relates to novel compounds which contain no sulfur or chlorine, and which thus contribute to the cleaning of the environment as organo-metal complexes used in metal pastes, etc., and a method for manufacturing the same.Metal acetylide compounds expressed by the general formula M(--C.tbd.C--R).sub.n (in the formula, M indicates a metal atom, n indicates the valence number of the metal atom M, and R indicates a hydrocarbon group with 1 to 8 carbon atoms which may or may not contain an oxygen atom) are provided as novel organo-metal complexes. Since these compounds contain no sulfur or chlorine, there is no release of sulfurous acid gas or chlorine compounds when the compounds are used in metal pastes, etc., even if the pastes are fired. Accordingly, these compounds contribute to the cleaning of the environment.Type: GrantFiled: May 24, 1999Date of Patent: November 21, 2000Assignee: Daiken Chemical Co., Ltd.Inventors: Akio Harada, Yoshiki Okamoto
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Patent number: 6146608Abstract: A metal hydride derivative wherein at least one hydrogen atom is replaced by deuterium (.sup.2.sub.1 H) or tritium (.sup.3.sub.1 H) isotope. The metal constituent of such metal hydride may be a Group III, IV or V metal or a transition metal, e.g., antimony, aluminum, gallium, tin, or germanium. The isotopically stabilized metal hydride derivatives of the invention are useful as metal source compositions for chemical vapor deposition, assisted chemical vapor deposition (e.g., laser-assisted chemical vapor deposition, light-assisted chemical vapor deposition, plasma-assisted chemical vapor deposition and ion-assisted chemical vapor deposition), ion implantation, molecular beam epitaxy, and rapid thermal processing.Type: GrantFiled: November 24, 1997Date of Patent: November 14, 2000Assignee: Advanced Technology Materials, Inc.Inventors: Michael A. Todd, Thomas H. Baum, Gautam Bhandari
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Patent number: 6102993Abstract: Copper precursor formulations, including a copper precursor with at least one of (a) water, (b) a water precursor and (c) a non-ligand organic hydrate, are useful in CVD processes, e.g., in liquid delivery chemical vapor deposition, for forming a copper-containing material on a substrate. The disclosed copper precursor formulations are particularly useful in the formation of copper layers in semiconductor integrated circuits, e.g., for metallization of interconnections in such semiconductor device structures.Type: GrantFiled: August 3, 1999Date of Patent: August 15, 2000Assignee: Advanced Technology Materials, Inc.Inventors: Gautam Bhandari, Thomas H. Baum, Chongying Xu
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Patent number: 6090963Abstract: A metal(hfac), alkene ligand precursor has been provided. The alkene ligand includes double bonded carbon atoms, with first and second bonds to the first carbon atom, and third and fourth bonds to the second carbon atom. The first, second, third, and fourth bonds are selected from a the group consisting of H, C.sub.1 to C.sub.8 alkyl, C.sub.1 to C.sub.8 haloalkyl, and C.sub.1 to C.sub.8 alkoxyl. As a general class, these precursors are capable of high metal deposition rates and high volatility, despite being stable in the liquid phase at low temperatures. Copper deposited with this precursor has low resistivity and high adhesive characteristics. A synthesis method has been provided which produces a high yield of the above-described alkene ligand class of metal precursors.Type: GrantFiled: March 30, 1999Date of Patent: July 18, 2000Assignee: Sharp Laboratories of America, Inc.Inventors: Wei-Wei Zhuang, Tue Nguyen, Robert Barrowcliff, David Russell Evans, Sheng Teng Hsu
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Patent number: 6090964Abstract: A liquid organocuprous compound of formula (I) of the present invention can be conveniently used in a low-temperature CVD process for the production of a contaminant-free copper film having good step-coverage and hole-filling properties: ##STR1## wherein: R.sup.1 represents a C.sub.3-8 cycloalkyl group, andR.sup.2 and R.sup.3 are each independently a perfluorinated C.sub.1-4 alkyl group.Type: GrantFiled: January 19, 1999Date of Patent: July 18, 2000Assignee: Postech FoundationInventors: Shi-Woo Rhee, Doo-Hwan Cho, Jai-Wook Park, Sang-Woo Kang
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Two powder synthesis of hydrotalcite and hydrotalcite-like compounds with monovalen inorganic anions
Patent number: 5776424Abstract: There is provided a method for making a monovalent inorganic anion-intercalated hydrotalcite-like material by first reacting a magnesium-containing powder and a transition alumina powder in a carboxylic acid-free, aqueous suspension to form a meixnerite intermediate. This intermediate is then contacted with a monovalent inorganic anion, in its acid or soluble salt form, to make a hydrotalcite-like material. The latter is then separated from the suspension. Representative materials include a bromide-, chloride-, nitrate- or vanadate-intercalated, hydrotalcite-like material.Type: GrantFiled: April 9, 1996Date of Patent: July 7, 1998Assignee: Aluminum Company of AmericaInventors: Edward S. Martin, John M. Stinson, Vito Cedro, III, William E. Horn, Jr. -
Patent number: 5730951Abstract: There is provided a method for making a polyvalent inorganic anion-intercalated hydrotalcite-like material by first reacting a magnesium-containing powder and a transition alumina powder in a carboxylic acid-free, aqueous suspension to form a meixnerite intermediate. This intermediate is then contacted with a polyvalent inorganic anion, in its acid, acid salt or ammonium salt form, to make a hydrotalcite-like material. The latter is then separated from the suspension. Representative materials include a borate- metatungstate- and paramolybdate-intercalated hydrotalcite-like material.Type: GrantFiled: May 14, 1996Date of Patent: March 24, 1998Assignee: Aluminum Company of AmericaInventors: Edward S. Martin, John M. Stinson, Vito Cedro, III, William E. Horn, Jr.
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Patent number: 5728366Abstract: There is provided a method for making monovalent organic anion-intercalated hydrotalcite-like materials by first reacting a magnesium-containing powder and a transition alumina powder in a carboxylic acid-free, aqueous suspension to form a meixnerite intermediate. This intermediate is then contacted with a monovalent organic anion to form a hydrotalcite-like material. The latter is then separated from the suspension. Representative materials include a stearate-, acetate- or benzoate-intercalated hydrotalcite-like material.Type: GrantFiled: May 14, 1996Date of Patent: March 17, 1998Assignee: Aluminum Company of AmericaInventors: Edward S. Martin, John M. Stinson, Vito Cedro, III, William E. Horn, Jr.
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Patent number: 5728363Abstract: There is provided an improved method for making synthetic hydrotalcite by first reacting powdered magnesium oxide with a high surface area, transition alumina in a solution or suspension to form a meixnerite-like intermediate. This intermediate is then contacted with an anion source such as an acid, and most preferably carbon dioxide, to form the layered double hydroxide which is separated from the suspension by filtering, centrifugation, vacuum dehydration or other known means. On a preferred basis, the transition alumina combined with activated magnesia consists essentially of an rehydratable alumina powder having a surface area of 100 m.sup.2 /g or greater. To make related double hydroxide compounds, still other reactants such as bromides, chlorides, boric acids, or salts thereof, may be substituted for the carbon dioxide gas fed into this suspension.Type: GrantFiled: March 28, 1996Date of Patent: March 17, 1998Assignee: Aluminum Company of AmericaInventors: Edward S. Martin, John M. Stinson, William E. Horn, Jr., Vito Cedro, III
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Patent number: 5728365Abstract: There is provided a method for making a divalent inorganic anion-intercalated hydrotalcite-like material by first reacting a magnesium-containing powder and a transition alumina powder in a carboxylic acid-free aqueous suspension to form a meixnerite intermediate. This intermediate is then contacted with a divalent inorganic anion, in its acid, acid salt or ammonium salt form, to make a hydrotalcite-like material. The latter is then separated from the suspension. Representative materials include a sulfate- and metavanadate-intercalated hydrotalcite-like material.Type: GrantFiled: May 14, 1996Date of Patent: March 17, 1998Assignee: Aluminum Company of AmericaInventors: Edward S. Martin, John M. Stinson, Vito Cedro, III, William E. Horn, Jr.
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Patent number: 5728364Abstract: There is provided an improved method for making synthetic hydrotalcite by first reacting a divalent metal compound with a trivalent metal oxide powder in a carboxylic acid-free, aqueous solution or suspension to form an intermediate. This intermediate is then contacted with an anion source such as carbon dioxide; a carbonate-containing compound; an acid or an ammonium salt to form a layered double hydroxide having the formula:A.sub.1-x B.sub.x (OH).sub.2 C.sub.z.mH.sub.2 O, where A represents a divalent metal cation, B represents a trivalent metal cation, C represents a mono- to polyvalent anion, and x, z and m satisfy the following conditions: 0.09<x<0.67; z=x/n, where n=the charge on the anion; and 2>m>0.5. Said layered double hydroxide is typically separated from the suspension by filtering, centrifugation, vacuum dehydration or other known means.Type: GrantFiled: April 9, 1996Date of Patent: March 17, 1998Assignee: Aluminum Company of AmericaInventors: Edward S. Martin, John M. Stinson, Vito Cedro, III, William E. Horn, Jr.
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Patent number: 5693261Abstract: Pentafluorophenylmagnesium halides are prepared by a Grignard exchange reaction of hydrocarbylmagnesium halide with pentafluorochlorobenzene. The pentafluorophenylmagnesium halides are converted to pentafluorophenyl metal or metalloid derivatives by reacting them with metal or metalloid halides such as BF.sub.3.Type: GrantFiled: August 9, 1995Date of Patent: December 2, 1997Assignee: Albemarle CorporationInventors: Niomi L. Krzystowczyk, Steven P. Diefenbach, Wendy L. Lemoine
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Patent number: 5684177Abstract: In a process for making synthetic prostaglandin-type compounds such as misoprostol, organo metallic cuprate complexes capable of reacting with cyclopentenones are prepared by reaction of an alkyl lithium compound with a cuprous halide, followed by reaction of the resulting complex with a vinyl stannane, using an excess of alkyl lithium in the initial reaction and maintaining the excess present during the formation of the organo metallic cuprate complex.Type: GrantFiled: May 17, 1996Date of Patent: November 4, 1997Assignee: Torcan Chemical Ltd.Inventors: Yee-Fung Lu, Raymond So, Dan To, Casimir G. Antczak
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Patent number: 5578286Abstract: There is provided a method for making a divalent or polyvalent organic anion-intercalated hydrotalcite-like materials by first reacting a magnesium-containing powder and a transition alumina powder in an aqueous suspension to form a meixnerite intermediate. This intermediate is then contacted with a dicarboxylate or polycarboxylate anion to form a hydrotalcite-like material. The latter is then separated from the suspension. Representative materials include an oxalate-, succinate- or terephthalate-intercalated hydrotalcite-like material.Type: GrantFiled: June 7, 1995Date of Patent: November 26, 1996Assignee: Aluminum Company of AmericaInventors: Edward S. Martin, John M. Stinson, Vito Cedro, III, William E. Horn, Jr.
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Patent number: 5501808Abstract: Transition metal compounds of a crystalline-like structure are provided having unique electrical properties. The compounds comprising nickel have been shown to have ferromagnetic behavior which is induced or enhanced by exposure to electromagnetic radiation and heat. The compounds are identified by characteristic peaks in the infrared spectra and X-ray powder diffraction spectra. The spectra suggest the compounds have a planar structure of the empirical formula M(X).sub.(4-Y)/X M.sub.C (Y)C.sub.4 or a three-dimensional structure of empirical formula M(X).sub.(6-Y)/X M.sub.C (Y)C.sub.6, wherein M.sub.C (Y) is the transition metal, with Y being its ionic state, and M(X) is the counter cation with X being its ionic state.Type: GrantFiled: April 18, 1994Date of Patent: March 26, 1996Inventor: Philip Patalano
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Patent number: 5449799Abstract: Described is the deposition of copper-containing layers on substrates by decomposition of organometallic copper compounds containing acetylacetonato or substituted acetylacetonato and isonitrile. The decomposition is preferably carried out in accordance with CVD method.Type: GrantFiled: July 6, 1993Date of Patent: September 12, 1995Inventors: Christian Terfloth, Thomas Kruck
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Patent number: 5420321Abstract: Tris(isonitrile)copper(I) sulfate complexes and their use in synthetic methods for making radionuclide isonitrile coordination complexes such as [.sup.99m Tc(1-isocyano-2-methoxy-2-methylpropane).sub.6 ].sup.+. The coordination complexes are useful as radiopharmaceutical imaging agents.Type: GrantFiled: August 3, 1993Date of Patent: May 30, 1995Assignee: The Du Pont Merck Pharmaceutical CompanyInventor: David S. Edwards
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Patent number: 5405981Abstract: A general method for sequential addition of two substituents to an .alpha.,.beta.-unsaturated ketone (enone), involving 1,4-conjugate addition of a desired substituent group to the enone to form an intermediate enolate, followed by electrophilic trapping of the enolate, wherein catalytic amounts of copper are employed in combination with another organometallic compound to effect the conjugate addition via a reactive cuprate reagent and yet provide an intermediate enolate species based on the other organometallic compound which is amenable to trapping by a suitable electrophile. Pursuant to this method, a true three-component coupling reaction can be effected starting from an alkyne, an enone, and an electrophile.Type: GrantFiled: March 26, 1993Date of Patent: April 11, 1995Assignee: The Regents of the University of CaliforniaInventor: Bruce H. Lipshutz
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Patent number: 5364953Abstract: The present invention relates to novel compounds for use as imaging agents. In particular, the present invention relates to paramagnetic metal clusters having oxygen and/or nitrogen containing ligands useful as contrast agents for magnetic resonance imaging (MRI).Type: GrantFiled: November 5, 1992Date of Patent: November 15, 1994Assignee: Mallinckrodt Medical, Inc.Inventors: Julie A. Beaty, Edward A. Deutsch, Dennis L. Nosco
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Patent number: 5306836Abstract: Fluorinated alkoxy compounds of copper, copper-calcium, copper-strontium, and copper-barium having the structure:Cu.sub.W (OR).sub.X Y.sub.Y L.sub.Z ; orM.sub.a Ci.sub.b (OR).sub.c,in which 1.ltoreq.w.ltoreq.4; R is a fluorinated alkyl group; x.gtoreq.1; Y is an alkoxy or alkyl group without beta-hydrogen; y.gtoreq.0; w.ltoreq.(x +y).ltoreq.2w; L is a Lewis base; 0.ltoreq.z.ltoreq.2w; M is Ca, Sr, or Ba; and 1.ltoreq.a.ltoreq.4; 1.ltoreq.b.ltoreq.4; (b+2a).ltoreq.c.ltoreq.2(b+a), have exceptionally high volatilities, and hence low vaporization or sublimation temperatures, at 10.sup.-5 torr. They are superior precursor compounds for chemical vapor deposition of thin films on substrates under vacuum, and for sol-gel processing.Type: GrantFiled: March 10, 1993Date of Patent: April 26, 1994Assignee: The United States of America as represented by the Secretary of the NavyInventor: Andrew Purdy
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Patent number: 5304237Abstract: A water-soluble chromium-free wood preservative comprising at least one copper salt and an alkanolamine and a polymeric quaternary ammonium borate formed by simultaneous reaction of (A) an amine selected from the group consisting of ##STR1## wherein R.sub.1 is alkyl or alkenyl of 8 to 22 carbon atoms or when R.sub.2 and R.sub.3 are --(C.sub.2 H.sub.4 O).sub.x --H or --(C.sub.3 H.sub.6 O).sub.x --H, R.sub.1 is alkyl of 1 to 22 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 22 carbon atoms, --(C.sub.2 H.sub.4 O).sub.x --H, --(C.sub.3 H.sub.6 O).sub.x --H and --CH.sub.2 --CH.sub.2 --NH.sub.2, R.sub.3 is selected from the group consisting of hydrogen, --(C.sub.2 H.sub.4 O).sub.x --H, --(C.sub.3 H.sub.6 O).sub.x --H and CH.sub.2 --CH.sub.2 --CH.sub.2 NH.sub.2, R.sub.4 and R.sub.6 are individually alkyl of 1 to 4 carbon atoms or --(CH.sub.2 H.sub.4 O).sub.x --H or --(C.sub.3 H.sub.6 O).sub.x --H, R.sub.5 and R.sub.2 are individually --(C.sub.2 H.sub.4 O).sub.x --H or -- (.Type: GrantFiled: January 21, 1993Date of Patent: April 19, 1994Assignee: Rutgerswerke Aktiengesellschaft AGInventors: Volker Barth, Helmut Hartner
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Patent number: 5286889Abstract: Higher order cuprate complexes are prepared by means of a transmetalation from a corresponding zirconate intermediate. This process is particularly valuable with respect to the preparation of vinylic side chains such as are present in prostaglandins, as it is possible in accordance with the present invention to proceed directly from the acetylenic precursors via the reactive cuprates to the desired final products in a one-pot operation without isolation of intermediates and in high yields. Sequential additions to zirconium intermediates of components which together comprise the cuprate involved in transmetalation with the zirconium intermediate are disclosed as alternative procedures.Type: GrantFiled: February 22, 1993Date of Patent: February 15, 1994Assignee: Regents of the University of CaliforniaInventors: Bruce H. Lipshutz, Edmund L. Ellsworth
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Patent number: 5281733Abstract: A process for the carbonylation of substituted metal coordination compounds in the presence of carbon monoxide at a pressure in excess of 400 psig to produce optionally substituted cyclopentadienyl metallic carbonyls, particularly methylcyclopentadienyl manganese tricarbonyl in a thin-film-producing reactor.Type: GrantFiled: June 4, 1992Date of Patent: January 25, 1994Assignee: Ethyl CorporationInventors: Carl O. Inabinet, Fred H. Gregory, David M. Marchand, Robert B. Agee
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Patent number: 5252763Abstract: A process for preparing higher order cuprate complexes by reacting an alkyne with zirconocene chloride hydride to produce a zirconium intermediate which is reacted with an alkyllithium and a first copper reagent selected from R.sup.2 Cu(CN)Li or the mixture CuCN and R.sup.2 Li to produce a higher order cuprate complex.Type: GrantFiled: July 8, 1992Date of Patent: October 12, 1993Assignee: G. D. Searle & Co.Inventors: Kevin A. Babiak, James R. Behling, John H. Dygos, John S. Ng
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Patent number: 5245064Abstract: The present invention provides a compound of the formula: ##STR1## wherein R.sup.1 is (C.sub.1 -C.sub.5)perfluoroalkyl, R.sup.2 is (C.sub.1 -C.sub.5)perfluoroalkyl or (C.sub.1 -C.sub.5)alkyl, R.sup.3 is (C.sub.1 -C.sub.5)perfluoroalkyl or (C.sub.1 -C.sub.5)alkyl, R.sup.4 is (C.sub.1 -C.sub.5)alkyl and R.sup.5 is (C.sub.1 -C.sub.5)alkyl, with the proviso that no more than two of R.sup.1, R.sup.2 and R.sup.3 can be (C.sub.1 -C.sub.5)perfluoroalkyl; and transition metal complexes thereof.Type: GrantFiled: August 14, 1992Date of Patent: September 14, 1993Inventors: Paul G. Gassman, John R. Sowa, John W. Mickelson
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Patent number: 5166382Abstract: Higher order cuprate complexes are prepared by means of a transmetalation from a corresponding zirconate intermediate. This process is particularly valuable with respect to the preparation of vinylic side chains such as are present in prostaglandins, as it is possible in accordance with the present invention to proceed directly from the acetylenic precursors via the reactive cuprates to the desired final products in a one-pot operation without isolation of intermediates and in high yields. Sequential additions to zirconium intermediates of components which together comprise the cuprate involved in transmetalation with the zirconium intermediate are disclosed as alternative procedures.Type: GrantFiled: August 20, 1991Date of Patent: November 24, 1992Assignee: Regents of the University of CaliforniaInventors: Bruce Howard, Edmund L. Ellsworth
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Patent number: 5134238Abstract: Disclosed herein is a class of chiral copper-amine complexes of the formula R(L*) CuLi in which L* is selected from: ##STR1## In this formula, R is a transferable ligand, which can be alkyl, aryl or aralkyl. M is a metal ion such as Li, Na, K, Cs, Rb, Be, Mg and other metal ions from the first two columns of the periodic table. R.sub.1 is straight chain alkyl, R.sub.2 is aryl or substituted aryl and R.sub.3 and R.sub.4 form a heterocyclic ring or a substituted heterocyclic ring with 4 to 8 members including oxygen and sulfur.Such complexes react with .alpha.,.beta.-unsaturated ketones, aldehydes, esters and other carbonyl containing compounds such that R is transferred to the 3 position enantioselectively as shown below. ##STR2## Such complexes react with .alpha.,.beta.-unsaturated ketones in the presence of trialkysilyl halides to give silyl enol ether in which R is substituted in the 3 position as shown below.Type: GrantFiled: July 15, 1991Date of Patent: July 28, 1992Assignee: Brigham Young UniversityInventors: Bryant E. Rossiter, Masakatsu Eguchi
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Patent number: 5072010Abstract: Higher order cuprate complexes are prepared by means of a transmetalation from a corresponding zirconate intermediate. This process is particularly valuable with respect to the preparation of vinylic side chains such as are present in prostaglandins, as it is possible in accordance with the present invention to proceed directly from the acetylenic precursors via the reactive cuprates to the desired final products in a one-pot operation without isolation of intermediates and in high yields. Sequential additions to zirconium intermediates of components which together comprise the cuprate involved in transmetalation with the zirconium intermediate are disclosed as alternative procedures.Type: GrantFiled: April 4, 1990Date of Patent: December 10, 1991Assignee: University of CaliforniaInventors: Bruce H. Lipshutz, Edmund L. Ellsworth
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Patent number: 5055592Abstract: This invention relates to the novel processes for the preparation of a 16-methoxy-16-methyl prostaglandin E.sub.1 derivative and to the novel intermediates useful therefor.Type: GrantFiled: January 30, 1990Date of Patent: October 8, 1991Assignee: Merrell Dow PharmaceuticalsInventors: Michael Kolb, Luc Van Hijfte
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Patent number: 5023213Abstract: A process for making ammonolytic precursors to nitride and carbonitride ceramics. Extreme reaction conditions are not required and the precursor is a powder-like substance that produces ceramics of improved purity and morphology upon pyrolysis.Type: GrantFiled: December 9, 1986Date of Patent: June 11, 1991Assignee: United States Department of EnergyInventor: Leon Maya
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Patent number: 5023360Abstract: Dialkyl gold(III) .beta.-diketonates are synthesized in a two-step, one-pot process using a gold trihalide, an alkyl lithium compound and a .beta.-diketone.Type: GrantFiled: May 1, 1990Date of Patent: June 11, 1991Assignee: International Business Machines CorporationInventors: Thomas H. Baum, Phillip J. Brock, Daniel J. Dawson
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Patent number: 5008418Abstract: Tris(isonitrile)copper(I) complex salts with anions selected from BF.sub.4, PF.sub.6, ClO.sub.4, I, Br, Cl and CF.sub.3 COO are useful in preparing radionuclide complexes rapidly at room temperature. Preferred isonitrile ligands are ether isonitriles. The tris(isonitrile)copper(I) adducts enable technetium complexes, such as those of Tc99m, to be prepared easily just prior to their use as imaging agents.Type: GrantFiled: August 23, 1989Date of Patent: April 16, 1991Assignee: E. I. du Pont de Nemours and CompanyInventors: Tahir Iqbal, John H. Cain, Jr., Jack J. Slosky
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Patent number: 4927670Abstract: Mixed metal oxide films containing Group IIa metals and transition metals are deposited on a heated substrate by a chemical vapor deposition process using alkylcyclopentadienyl metal compound precursors and an oxidizing agent.Type: GrantFiled: June 22, 1988Date of Patent: May 22, 1990Assignee: Georgia Tech Research CorporationInventor: Ahmet Erbil
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Patent number: 4915988Abstract: Coatings of Group IIA metals and compounds thereof are formed by chemical vapor deposition, in which a heat decomposable organometallic compound of the formula (I) ##STR1## where M is a Group IIA metal, preferably magnesium, calcium, strontium, or barium and R is a lower alkyl or alkenyl radical containing from 2 to about 6 carbon atoms, with a heated substrate which is above the decomposition temperature of the organometallic compound. The pure metal is obtained when the compound of the formula I is the sole heat decomposable compound present and deposition is carried out under nonoxidizing conditions. Intermetallic compounds such as barium selenide can be deposited from a barium compound of formula I and a heat decomposable selenium compound under nonoxidizing conditions. Group II metal oxides and salts, such as barium titanate, are obtainable by deposition from a compound of formula I (and an additional titanium organometallic compound (under oxidizing conditions.Type: GrantFiled: June 22, 1988Date of Patent: April 10, 1990Assignee: Georgia Tech Research CorporationInventor: Ahmet Erbil
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Patent number: 4785124Abstract: This invention encompasses a process for preparing higher order cuprate complexes which contain a carbanion for the formation of carbon to carbon bonds in reactions such as epoxide addition. The complex is formed by reacting a first cuprate complex with a stannane such that the carbanion to be used to form carbon to carbon bonds is transferred from the stannane to the first cuprate complex to form a different higher order cuprate complex. This process permits the in situ preparation of a higher order cuprate complex having the carbanion desired to be used in a synthetic reaction. Higher order cuprate complexes derived from the reaction of a cuprate complex with 1,2-bis-tri-n-butylstannyl ethylene are particularly useful for the addition to epoxides to form vinyl tin intermediates useful for preparing omega side chains of prostaglandins.Type: GrantFiled: June 8, 1987Date of Patent: November 15, 1988Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, James R. Behling, Sau-hoi N. John, Kevin A. Babiak
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Patent number: 4777275Abstract: This invention encompasses a process for preparing higher order cuprate complexes which contain a carbanion for the formation of carbon to carbon bonds in reactions such as 1,4-conjugate addition. The complex is formed by reacting a first cuprate complex with a stannane such that the carbanion to be used to form carbon to carbon bonds is transferred from the stannane to the first cuprate complex to form a different higher order cuprate complex. This process permits the in situ preparation of a higher order cuprate complex having the carbanion desired to be used in a synthetic reaction. Higher order cuprate complexes prepared by this process are particularly useful for the efficient preparation of pharmacologically active prostaglandins.Type: GrantFiled: June 9, 1987Date of Patent: October 11, 1988Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, James R. Behling
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Patent number: 4767873Abstract: The invention describes a helicene compound having the structure ##SPC1##which contains seven six-membered conjugated aromatic rings capped by two five-membered rings which do not superimpose on each other.The invention also describes a helical metallocene oligomer capped by unsaturated five-membered rings, having the structure: ##SPC2##wherein M is a transition metal halide and n=1 to 100.Method for the preparation of these compounds are also presented.Type: GrantFiled: September 10, 1986Date of Patent: August 30, 1988Assignee: The Trustees of Columbia University in the City of New YorkInventors: Thomas J. Katz, Anantha Sudhakar