Containing -c(=x)-, Wherein X Is Chalcogen Patents (Class 556/117)
  • Patent number: 8962876
    Abstract: A precursor for the deposition of a thin film by atomic layer deposition is provided. The compound has the formula MxLy where M is a metal and L is an amidrazone-derived ligand or an amidate-derived ligand. A process of forming a thin film using the precursors is also provided.
    Type: Grant
    Filed: May 17, 2010
    Date of Patent: February 24, 2015
    Assignee: Wayne State University
    Inventors: Charles H. Winter, Thomas Joseph Knisley, Panditha Koralalage Don Mahesh Chinthaka Karunarathne
  • Publication number: 20140352855
    Abstract: The reaction product of a nitro aromatic and a metal hydroxyl nitrate is presented. Gas generating compositions containing the reaction product are also presented. Gas generators and vehicle occupant protection systems containing the reaction product are also presented.
    Type: Application
    Filed: June 3, 2014
    Publication date: December 4, 2014
    Applicant: TK Holdings Inc.
    Inventors: Sudhakar R Ganta, Scott M. Rambow, Deborah L. Hordos
  • Publication number: 20140303109
    Abstract: Water-soluble fluorinated analogs of natural curcumin, and particularly difluoro Knoevenagel condensates and Schiff bases, along with their corresponding copper (H) complexes have improved bioavailablity over curcumin. The fluorine-substituted analogs of curcumin are useful as chemopreventive and/or therapeutic agents against cancers and/or against the development of drug-resistant cancer. A preferred compound is (IE,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene{4(3,4 difluorobenzaldehyde)}-3,5-dione.
    Type: Application
    Filed: March 25, 2011
    Publication date: October 9, 2014
    Inventors: Fazlul H. Sarkar, Subhash Padhye
  • Patent number: 8729285
    Abstract: A copper complex compound represented by Formula (1) is disclosed. in the formula, groups represented by R is a substituent, n is an integer of from 1 to 5 and the total carbon number contained in (R)n is 14 or more. A toner for electrophotography containing the compound is also disclosed.
    Type: Grant
    Filed: March 3, 2011
    Date of Patent: May 20, 2014
    Assignee: Konica Minolta Business Technologies, Inc.
    Inventors: Koji Daifuku, Ryohei Iwamoto, Keiko Ishidai, Kimihiko Ookubo, Kaori Ono, Issei Nakahara
  • Patent number: 8692010
    Abstract: Disclosed are synthesis methods to produce copper bis-ketoiminate and copper bis-ketiminate compounds.
    Type: Grant
    Filed: July 13, 2012
    Date of Patent: April 8, 2014
    Assignee: American Air Liquide, Inc.
    Inventors: Andrey V. Korolev, Venkateswara R. Pallem
  • Publication number: 20140087409
    Abstract: Provided are near-infrared silver sulfide quantum dots, a preparation method thereof and a biological application thereof. The silver sulfide quantum dots have hydrophilic groups derived from a mercapto-containing hydrophilic reagent attached on the surface thereof, and the hydrophilic reagent is any one of mercaptoacetic acid, mercaptopropionic acid, cysteine, cysteamine, thioctic acid and ammonium mercaptoacetate or any combination thereof. The silver sulfide quantum dots have high fluorescence yield, good fluorescence stability, good biocompatibility and uniform sizes. The preparation method has moderate reaction conditions, simple operation, short production cycle, good reproducibility and is easy to control. The silver sulfide quantum dots can be used in the application of cellular imaging and biological tissue imaging.
    Type: Application
    Filed: February 10, 2012
    Publication date: March 27, 2014
    Applicant: Suzhou Institute of Nano-Bionics, Shinese Academy of Sciences
    Inventors: Qiangbin Wang, Yejun Zhang
  • Publication number: 20130253213
    Abstract: Provided is a method for producing cyanoacetic acid in a hydrolysis reaction of a predetermined cyanoacetate in the presence of an acid catalyst. Further, are provided methods for producing a cyanoacetic acid derivative and a metal containing compound by using the produced cyanoacetic acid as a staring material. Herein, the method for producing cyanoacetic acid enables the content of a malonic acid byproduct generated in the hydrolysis reaction to be greatly lowered, allowing the produced cyanoacetic acid to be used as a starting material without any purification treatments. Those advantageous effects result in the great improvement in the purity and yields of the cyanoacetic acid derivative and the metal containing compound produced by said cyanoacetic acid. Accordingly, the above mentioned methods make it possible to produce cyanoacetic acid, the cyanoacetic acid derivative and the metal containing compound, as excellent in the productivity and economical efficiency.
    Type: Application
    Filed: March 15, 2013
    Publication date: September 26, 2013
    Applicant: Konica Minolta Business Technologies, Inc.
    Inventors: Dai IKEMIZU, Ryohei IWAMOTO, Keiko ISHIDAI, Kimihiko OOKUBO
  • Patent number: 8530559
    Abstract: Provided is a composite including copper nanoparticles or copper(I) oxide nanoparticles and a thioether-containing organic compound represented by X(OCH2CHR1)nOCH2CH(OH)CH2SZ [X represents an alkyl group; R1 represents a hydrogen atom or a methyl group; n represents an integer of 2 to 100; R1 is independent between repeating units and may be the same or different; and Z represents an alkyl group, an allyl group, an aryl group, an arylalkyl group, —R2—OH, —R2—NHR3, or —R2—(COR4)m (where R2 represents a saturated hydrocarbon group; R3 represents a hydrogen atom, an acyl group, an alkoxycarbonyl group, or a benzyloxycarbonyl group; R4 represents a hydroxy group, an alkyl group, or an alkoxy group; and m represents 1 to 3)].
    Type: Grant
    Filed: February 28, 2011
    Date of Patent: September 10, 2013
    Assignee: DIC Corporation
    Inventors: Yoshiyuki Sano, Ren-Hua Jin, Kaori Kawamura, Masafumi Uota
  • Patent number: 8475685
    Abstract: A particle includes: a metal; and a compound containing a hydrogen-bonding forming group, an absorption group different from the hydrogen-bonding forming group, and an aromatic ring, M representing the metal, A representing the absorption group, B representing the hydrogen-bonding forming group, a representing an integer of 0 or greater, b representing an integer of 0 or greater, c representing an integer of 1 or greater, R1 representing an aromatic ring (a planar ring up to a pi-electron number of 24) and a derivative of the aromatic ring, R2 through R5 representing a hydrogen atom, saturated hydrocarbon, unsaturated hydrocarbon, an ether bond, an ester bond, a cyano group, or derivatives of the substances and bonds, and the compound having a structure expressed by the following chemical formula.
    Type: Grant
    Filed: March 12, 2010
    Date of Patent: July 2, 2013
    Assignees: Kabushiki Kaisha Toshiba, Institute of National Colleges of Technology, Japan
    Inventors: Ko Yamada, Kenji Todori, Shigeru Machida
  • Publication number: 20130095320
    Abstract: Provided is a composite including copper nanoparticles or copper(I) oxide nanoparticles and a thioether-containing organic compound represented by X(OCH2CHR1)nOCH2CH(OH)CH2SZ [X represents an alkyl group; R1 represents a hydrogen atom or a methyl group; n represents an integer of 2 to 100; R1 is independent between repeating units and may be the same or different; and Z represents an alkyl group, an allyl group, an aryl group, an arylalkyl group, —R2—OH, —R2—NHR3, or —R2—(COR4)m (where R2 represents a saturated hydrocarbon group; R3 represents a hydrogen atom, an acyl group, an alkoxycarbonyl group, or a benzyloxycarbonyl group; R4 represents a hydroxy group, an alkyl group, or an alkoxy group; and m represents 1 to 3)].
    Type: Application
    Filed: February 28, 2011
    Publication date: April 18, 2013
    Applicant: DIC CORPORATION
    Inventors: Yoshiyuki Sano, Ren-Hua Jin, Kaori Kawamura, Masafumi Uota
  • Publication number: 20120302815
    Abstract: A composition used to develop a reagent for investigating Ubl-modifications in cellular functions and in the treatment of cancer is provided. The composition comprises gold nanoparticle (AuNP)-ligand conjugates that include at least two components: gold nanoparticles (AuNPs) and modified ubiquitin- or ubiquitin-like interacting motif (UIM or ULIM) mimetics. In one embodiment, the modified ULM mimetic is a modified SUMO interaction motif (SIM) mimetic. According to the embodiments described herein, the compound inhibits ubiquitin- or ubiquitin-like protein (Ubl)-mediated protein-protein interactions and sensitizes cells to ionizing radiation. The modified UIM and ULIM mimetics may be conjugated to the AuNP such that each AuNP is conjugated to a plurality of modified UIM or ULIM mimetics. The modified ULIM mimetics may be conjugated to the AuNP via a thiol group.
    Type: Application
    Filed: February 21, 2012
    Publication date: November 29, 2012
    Inventors: Yuan Chen, David Horne, Yi-Jia Li, Yuelong Ma, Angela L. Perkins-Harki, Yang Su
  • Publication number: 20120058270
    Abstract: A precursor for the deposition of a thin film by atomic layer deposition is provided. The compound has the formula MxLy where M is a metal and L is an amidrazone-derived ligand or an amidate-derived ligand. A process of forming a thin film using the precursors is also provided.
    Type: Application
    Filed: May 17, 2010
    Publication date: March 8, 2012
    Applicant: WAYNE STATE UNIVERSITY
    Inventors: Charles H. Winter, Thomas Joseph Knisley, Panditha Koralalage Don Mahesh Chinthaka Karunarathne
  • Publication number: 20110235151
    Abstract: An electrochromic material including a metal-organic framework including a metal, and an organic compound including a functional group, wherein the organic compound forms a coordination complex with the metal.
    Type: Application
    Filed: July 21, 2010
    Publication date: September 29, 2011
    Applicant: SAMSUNG ELECTRONICS CO., LTD.
    Inventors: Chang-Ho NOH, Seog-Jin JEON, Seung-Uk SON
  • Publication number: 20110180968
    Abstract: A method for making a carbon nanotube metal composite includes the following steps. A number of carbon nanotubes is dispersed in a solvent to obtain a suspension. Metal powder is added into the suspension, and then the suspension agitated. The suspension containing the metal powder is allowed to stand for a while. The solvent is reduced to obtain a mixture of the number of carbon nanotubes and the metal powder.
    Type: Application
    Filed: October 15, 2010
    Publication date: July 28, 2011
    Applicants: TSINGHUA UNIVERSITY, HON HAI PRECISION INDUSTRY CO., LTD.
    Inventors: CHUN-HUA HU, CHANG-HONG LIU, SHOU-SHAN FAN
  • Publication number: 20110151117
    Abstract: There is provided organic metal complexes for forming a metal thin layer, ink including the same, and a method for forming a metal thin layer using the same: wherein the organic metal complexes for forming a metal thin layer include Ag, and a ligand represented by the specific general formula; the organic metal complexes have an excellent stability and solubility toward a solvent; and the ink for forming a metal thin layer comprising the organic metal complexes is easy to form a metal thin layer of, and could be applied on the substrate consisting of material having low thermal stability because the ink can be decomposed at a low temperature.
    Type: Application
    Filed: July 14, 2010
    Publication date: June 23, 2011
    Applicant: SAMSUNG ELECTRO-MECHANICS CO., LTD.
    Inventors: Young Kwan Seo, Dong Hoon Kim, Kwi Jong Lee
  • Publication number: 20100239219
    Abstract: A particle includes: a metal; and a compound containing a hydrogen-bonding forming group, an absorption group different from the hydrogen-bonding forming group, and an aromatic ring, M representing the metal, A representing the absorption group, B representing the hydrogen-bonding forming group, a representing an integer of 0 or greater, b representing an integer of 0 or greater, c representing an integer of 1 or greater, R1 representing an aromatic ring (a planar ring up to a pi-electron number of 24) and a derivative of the aromatic ring, R2 through R5 representing a hydrogen atom, saturated hydrocarbon, unsaturated hydrocarbon, an ether bond, an ester bond, a cyano group, or derivatives of the substances and bonds, and the compound having a structure expressed by the following chemical formula.
    Type: Application
    Filed: March 12, 2010
    Publication date: September 23, 2010
    Applicants: KABUSHIKI KAISHA TOSHIBA, INSTITUTE OF NATIONAL COLLEGES OF TECHNOLOGY
    Inventors: Ko Yamada, Kenji Todori, Shigeru Machida
  • Patent number: 7141688
    Abstract: The present invention is directed to novel fluorinated dye stabilizers having both high quenching efficiency and solubility in halogenated solvents. These dye stabilizers have shown a significantly effect on improving the dye fastness in hostile photooxidation conditions.
    Type: Grant
    Filed: October 14, 2003
    Date of Patent: November 28, 2006
    Assignee: SiPix Imaging, Inc.
    Inventors: Kai-Chia Feng, Ying-Syi Li, Jin Yang, HongMei Zang, Haiyan Gu, Sundaravel P. Ananthavel, Rong-Chang Liang
  • Patent number: 7008748
    Abstract: Thermally developable materials such as thermographic and photothermographic materials include a co-precipitate comprising first and second organic silver salts, the first organic silver salt comprising a silver salt of a nitrogen-containing heterocyclic compound containing an imino group, and the second organic silver salt comprising a silver salt of a mercaptotriazole. The first organic silver salt can be used in the imaging process as a source of reducible silver ions, and the second organic silver salt can be a source of a toning agent. The co-precipitate can be prepared using double-jet precipitation techniques to provide an aqueous dispersion that can be used in imaging formulations.
    Type: Grant
    Filed: September 7, 2004
    Date of Patent: March 7, 2006
    Assignee: Eastman Kodak Company
    Inventors: Dirk J. Hasberg, Doreen C. Lynch, Kui Chen-Ho, Chaofeng Zou
  • Patent number: 6992200
    Abstract: Copper-containing thin films can be industrially advantageously formed by chemical vapor deposition using as the copper source a divalent copper complex bearing ?-diketonato ligands having silyl ether linkage. A representative example of the divalent copper complex is represented by the formula (I): wherein Z is hydrogen or alkyl; X is a group represented by the formula (I—I), in which Ra is alkylene, and each of Rb, Rc and Rd is alkyl; and Y is an alkyl group or a group represented by the formula (I—I), in which Ra is alkylene, and each of Rb, Rc and Rd is alkyl.
    Type: Grant
    Filed: January 31, 2003
    Date of Patent: January 31, 2006
    Assignee: UBE Industries, Ltd.
    Inventors: Takumi Kadota, Chihiro Hasegawa, Kouhei Watanuki
  • Patent number: 6919467
    Abstract: The present invention provides a catalyst precursor and catalyst system comprising the precursor, an embodiment of the precursor is selected from the following structures: wherein T is a bridging group; M is selected from Groups 3 to 7 atoms, and the Lanthanide series of atoms the Periodic Table of the Elements; Z is a coordination ligand; each L is a monovalent, bivalent, or trivalent anionic ligand; X and Y are each independently selected from nitrogen, oxygen, sulfur, and phosphorus; R is a non-bulky substituent that has relatively low steric hindrance with respect to X; and R? is a bulky substituent that is sterically hindering with respect to Y.
    Type: Grant
    Filed: December 18, 2001
    Date of Patent: July 19, 2005
    Assignee: Univation Technologies, LLC
    Inventor: Rex Eugene Murray
  • Patent number: 6764537
    Abstract: A method for chemical vapor deposition of copper metal thin film on a substrate includes heating a substrate onto which the copper metal thin film is to be deposited in a chemical vapor deposition chamber; vaporizing a precursor containing the copper metal, wherein the precursor is a compound of (&agr;-methylstyrene)Cu(I)(hfac), where hfac is hexafluoroacetylacetonate, and (hfac)Cu(I)L, where L is an alkene; introducing the vaporized precursor into the chemical vapor deposition chamber adjacent the heated substrate; and condensing the vaporized precursor onto the substrate thereby depositing copper metal onto the substrate. A copper metal precursor for use in the chemical vapor deposition of a copper metal thin film is a compound of (&agr;-methylstyrene)Cu(I)(hfac), where hfac is hexafluoroacetylacetonate, and (hfac)Cu(I)L, where L is an alkene taken from the group of alkenes consisting of 1-pentene, 1-hexene and trimethylvinylsilane.
    Type: Grant
    Filed: June 2, 2003
    Date of Patent: July 20, 2004
    Assignee: Sharp Laboratories of America, Inc.
    Inventors: Wei-Wei Zhuang, Lawrence J. Charneski, David R. Evans, Sheng Teng Hsu
  • Publication number: 20040077714
    Abstract: Neutral alpha amino diacid complexes of trace minerals and their use for animal nutrition.
    Type: Application
    Filed: October 16, 2002
    Publication date: April 22, 2004
    Applicant: Zinpro Corporation
    Inventors: Mahmoud M. Abdel-Monem, Michael D. Anderson
  • Patent number: 6710197
    Abstract: A compound capable of efficiently cutting off light in the near infrared region, copper (meth)acryloyloxyethyl phosphate coordination complex, is synthesized including reacting (meth)acryloyloxyethyl phosphate and copper acetate monohydrate in water.
    Type: Grant
    Filed: November 12, 2002
    Date of Patent: March 23, 2004
    Assignee: Chung-Shan Institute of Science and Technology
    Inventors: Shean-Jeng Jong, Chong Ma
  • Patent number: 6703498
    Abstract: Water-soluble metal ion affinity compounds and methods for using the same are provided. The subject compounds include an aspartate based metal chelating ligand bonded to a water-soluble polymeric substrate, where the ligand is complexed with a metal ion. In certain embodiments, the subject compounds further include a member of a signal producing system, e.g., a directly or an indirectly detectable label moiety. Also provided are water-insoluble supports having the subject compounds present on, e.g., immobilized on, at least one surface thereof. The subject compounds find use in a variety of different applications, including analyte detection and analyte purification applications.
    Type: Grant
    Filed: June 20, 2002
    Date of Patent: March 9, 2004
    Assignee: Clontech Laboratories, Inc.
    Inventor: Grigoriy S. Tchaga
  • Publication number: 20040044073
    Abstract: A composition and process is disclosed for treating an acne infection with a composition of electrolytically generated silver citrate. The composition of electrolytically generated silver citrate may be applied topically to the acne infection in an aqueous solution or may be incorporated within a cosmetic product., The acne composition may be combined with a composition component such as a cosmetic, a lotion, an emulsion, a gel or a soap.
    Type: Application
    Filed: August 31, 2002
    Publication date: March 4, 2004
    Applicant: Innovative Medical Services
    Inventor: Andrew B. Arata
  • Patent number: 6682602
    Abstract: A method of forming a film on a substrate using one or more complexes containing one or more chelating O- and/or N-donor ligands. The complexes and methods are particularly suitable for the preparation of semiconductor structures using chemical vapor deposition techniques and systems.
    Type: Grant
    Filed: August 19, 2002
    Date of Patent: January 27, 2004
    Assignee: Micron Technology, Inc.
    Inventor: Brian A. Vaartstra
  • Patent number: 6642401
    Abstract: A &bgr;-diketonatocopper(I) complex which contains as a ligand (L) an allene compound and is represented by formula (2) wherein, R6 and R7 may be the same or different and each represents linear or branched C1-4 alkyl, C1-4 alkoxy, or linear or branched C1-4 fluoroalkyl, R8 represents hydrogen or fluorine, and L represents the allene compound, and a process for producing the same. The complex is useful in forming a thin copper film by metal-organic vapor deposition (hereinafter abbreviated as MOCVD) method.
    Type: Grant
    Filed: August 8, 2002
    Date of Patent: November 4, 2003
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Hisayuki Watanabe, Hideki Musashi, Yasuo Kawamura
  • Patent number: 6613924
    Abstract: Organosilver complexes with &bgr;-diketonates and neutral coordinating ligands are useful as silver precursors in chemical vapor deposition processes. The &bgr;-diketonates include 1,1,1,5,5,5-hexafluoro-2,4-pentanedionate (hfac), acetylacetonate (acac), 2,2,6,6-tetramethyl-3,5-heptanedionate (tmhd), 1,1,1-trifluoro-2,4-pentanedionate, (tfac), 2,2,7-trimethyl-3,5-octanedionate (tmod), 1,1,1-trifluoro-5,5-dimethyl-2,4-pentanedionate (tfh) 1,1,1,2,2,3,3,7,7,8,8,9,9,9-tetradecafluoro-4,6-nonanedionate (tdf). Neutral coordinating ligands include triphenylphosphine, tributylphosphine, pyridine, tetramethylethanediamine (TMEDA) and tetramethylpropanediamine (TMPDA).
    Type: Grant
    Filed: November 23, 1999
    Date of Patent: September 2, 2003
    Assignee: Research Foundation of State of New York
    Inventors: John T. Welch, Silvana C. Ngo, Kulbinder K. Banger
  • Patent number: 6534666
    Abstract: 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: Grant
    Filed: December 27, 2001
    Date of Patent: March 18, 2003
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Robert Sam Zorich, James Richard Thurmond, David Allen Roberts
  • Publication number: 20020143202
    Abstract: A method for chemical vapor deposition of copper metal thin film on a substrate includes heating a substrate onto which the copper metal thin film is to be deposited in a chemical vapor deposition chamber; vaporizing a precursor containing the copper metal, wherein the precursor is a compound of (&agr;-methylstyrene)Cu(I)(hfac), where hfac is hexafluoroacetylacetonate, and (hfac)Cu(I)L, where L is an alkene; introducing the vaporized precursor into the chemical vapor deposition chamber adjacent the heated substrate; and condensing the vaporized precursor onto the substrate thereby depositing copper metal onto the substrate. A copper metal precursor for use in the chemical vapor deposition of a copper metal thin film is a compound of (&agr;-methylstyrene)Cu(I)(hfac), where hfac is hexafluoroacetylacetonate, and (hfac)Cu(I)L, where L is an alkene taken from the group of alkenes consisting of 1-pentene, 1-hexene and trimethylvinylsilane.
    Type: Application
    Filed: March 27, 2001
    Publication date: October 3, 2002
    Inventors: Wei-Wei Zhuang, Lawrence J. Charneski, David R. Evans, Sheng Teng Hsu
  • Patent number: 6455717
    Abstract: A method of forming a film on a substrate using one or more complexes containing one or more chelating O- and/or N-donor ligands. The complexes and methods are particularly suitable for the preparation of semiconductor structures using chemical vapor deposition techniques and systems.
    Type: Grant
    Filed: August 28, 2000
    Date of Patent: September 24, 2002
    Assignee: Micron Technology, Inc.
    Inventor: Brian A. Vaartstra
  • Patent number: 6429325
    Abstract: A material for chemical vapor deposition comprising a &bgr;-diketonatocopper (II) complex which is liquid at room temperature.
    Type: Grant
    Filed: December 6, 2000
    Date of Patent: August 6, 2002
    Assignee: Asahi Denka Kogyo Kabushiki Kaisha
    Inventors: Kazuhisa Onozawa, Toshiya Shingen
  • Patent number: 6365746
    Abstract: This invention relates to an organomercapto Au(I) complex having the formula [(M—SOL)n—A—S—Au—S—A—(SOL—M)n]M wherein M is a cationic counterion; SOL is a solubilizing group: A is a substituted or unsubstituted divalent organic linking group; and n is 1 to 4 and wherein the compound is symmetrical. It further relates to a method of manufacturing an organomercapto Au(I) complex comprising reacting an Au (I) complex with an organomercapto ligand and isolating the resulting organomercapto Au(I) complex from the reaction mixture.
    Type: Grant
    Filed: December 27, 1999
    Date of Patent: April 2, 2002
    Assignee: Eastman Kodak Company
    Inventors: Roger Lok, Weimar W. White, Brian P. Cleary
  • Publication number: 20020010363
    Abstract: A method for the reduction in iodine content in a mixture, particularly in a mixture of carboxylic acids and/or carboxylic anhydrides with alkyl iodides and/or hydriodic acid, comprises contacting the organic medium in the vapor phase at elevated temperature with a metal salt dispersed on activated charcoal. The metal salt may be a carboxylate salt, a carbonate, an oxide, a hydroxide and any other salt, which may react with the organic medium to give a metal carboxylate salt. The metal may be a main group element, a lanthanide, an actinide, zinc and copper. This process converts alkyl iodide compounds converted to their corresponding carboxylate esters, while the iodine is bound in the purification mass as inorganic iodide.
    Type: Application
    Filed: December 21, 2000
    Publication date: January 24, 2002
    Inventor: Niels C. Schiodt
  • Patent number: 6281377
    Abstract: 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: Grant
    Filed: February 11, 2000
    Date of Patent: August 28, 2001
    Assignee: Sharp Laboratories of America, Inc.
    Inventors: Wei-Wei Zhuang, Tue Nguyen, Lawrence J. Charneski, David R. Evans, Sheng Teng Hsu
  • Patent number: 6102993
    Abstract: 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: Grant
    Filed: August 3, 1999
    Date of Patent: August 15, 2000
    Assignee: Advanced Technology Materials, Inc.
    Inventors: Gautam Bhandari, Thomas H. Baum, Chongying Xu
  • Patent number: 6096913
    Abstract: In a process for the synthesis of a first metal-ligand complex, M.sup.+n (L.sup.-).sub.n, where n.gtoreq.1, from a metal compound precursor and a ligand precursor, where the metal of the metal compound precursor may during the synthesis change to a valence in excess of n; the improvement, to suppress formation of a second metal-ligand complex of the metal with a valence in excess of n, of adding the elemental form of the metal to the synthesis of the first metal-ligand complex.
    Type: Grant
    Filed: June 10, 1999
    Date of Patent: August 1, 2000
    Assignee: Air Products and Chemicals, Inc.
    Inventors: John Anthony Thomas Norman, Yoshihide Senzaki, David Allen Roberts
  • Patent number: 6090964
    Abstract: 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: Grant
    Filed: January 19, 1999
    Date of Patent: July 18, 2000
    Assignee: Postech Foundation
    Inventors: Shi-Woo Rhee, Doo-Hwan Cho, Jai-Wook Park, Sang-Woo Kang
  • Patent number: 6090963
    Abstract: 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: Grant
    Filed: March 30, 1999
    Date of Patent: July 18, 2000
    Assignee: Sharp Laboratories of America, Inc.
    Inventors: Wei-Wei Zhuang, Tue Nguyen, Robert Barrowcliff, David Russell Evans, Sheng Teng Hsu
  • Patent number: 6046364
    Abstract: A process for recovering a 1,1,1,5,5,5-hexafluoro-2,4-pentanedione ligand from a metal-ligand complex byproduct such as Cu.sup.+2 (1,1,1,5,5,5-hexafluoro-2,4-pentanedionate.sup.-1).sub.2, comprising: providing a copper-ligand complex byproduct of Cu.sup.+2 (1,1,1,5,5,5-hexafluoro-2,4-pentanedionate.sup.-1).sub.2 in a process stream; cooling and condensing the copper-ligand complex byproduct of Cu.sup.+2 (1,1,1,5,5,5-hexafluoro-2,4-pentanedionate.sup.-1).sub.2 to separate it from the process stream; contacting the copper-ligand complex byproduct of Cu.sup.+2 (1,1,1,5,5,5-hexafluoro-2,4-pentanedionate.sup.-1).sub.2 with a protonation agent, such as: sulfuric acid, hydrochloric acid, hydroiodic acid, hydrobromic acid, trifluoroacetic acid, trifluoromethanesulfonic acid, acid ion exchange resin, hydrogen sulfide, water vapor and mixtures thereof; and recovering 1,1,1,5,5,5-hexafluoro-2,4-pentanedione.
    Type: Grant
    Filed: December 7, 1998
    Date of Patent: April 4, 2000
    Assignee: Air Products and Chemicals, Inc.
    Inventors: John Anthony Thomas Norman, John Cameron Gordon, Yoshihide Senzaki
  • Patent number: 6015918
    Abstract: A Cu(hfac) allyl-derived ligand precursor has been provided. The ligand includes group consisting of alkyl, phenyl, trialkylsilane, trialkoxylsilane, halodialkylsilane, dihaloalkylsilane, trihalosilane, triphenylsilane, alkoxyl, halogen, chloroformate, cynanide, cycloalkyl, cycloalkylamine, alkyl ether, isocyanate, and pentafluorobenzene. Examples of the allyl-derived ligand precursors have proved to be stable at room temperatures, and sufficiently volatile at higher 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 precursors, including a Cu(hfac)(allyltrimethylsilane) precursor.
    Type: Grant
    Filed: March 30, 1999
    Date of Patent: January 18, 2000
    Assignee: Sharp Laboratories of America, Inc.
    Inventors: Wei-Wei Zhuang, Tue Nguyen, Greg Michael Stecker, David Russell Evans, Sheng Teng Hsu
  • Patent number: 5994571
    Abstract: A Cu(hfac) precursor with a substituted ethylene ligand has been provided. The substituted ethylene ligand includes bonds to molecules selected from the group consisting of C.sub.1 to C.sub.8 alkyl, C.sub.1 to C.sub.8 haloalkyl, H, and C.sub.1 to C.sub.8 alkoxyl. One variation, the 2-methyl-1-butene ligand precursor has proved to be stable at room temperature, and extremely volatile at higher temperatures. Copper deposited with this precursor has low resistivity and high adhesive characteristics. Because of the volatility, the deposition rate of copper deposited with this precursor is very high. A synthesis method has been provided which produces a high yield of the above-described precursor.
    Type: Grant
    Filed: December 18, 1998
    Date of Patent: November 30, 1999
    Assignee: Sharp Laboratories of America, Inc.
    Inventors: Wei-Wei Zhuang, Tue Nguyen, Lawrence J. Charneski, David Russell Evans, Sheng Teng Hsu
  • Patent number: 5914097
    Abstract: The present invention relates to the preparation of amino-acyl-type and catecholamine-type compounds having multiple carboxylic acid functional groups. Paramagnetic metal (II) or (III) ion chelate complexes are formed using these compounds for use as intravenous contrast agents to produce enhanced contrast magnetic resonance images of the heart, liver, biliary tree or upper small intestine. The mono- and di-amino acids, their esters and amides, and catecholamine-like derivatives, of EDTA, DTPA, and the like are prepared. The paramagnetic metal (II) or (III) ion complexes are formed and produce T1-related contrast effects in MR images. The compounds and complexes also appear to have low toxicities and to be relatively rapidly and completely cleared from the tissue of a living mammal, e.g. a human being.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: June 22, 1999
    Assignee: Regents of the University of California
    Inventor: David L. White
  • Patent number: 5880149
    Abstract: The invention relates to metal complexes used to bind proteins and enzymes.
    Type: Grant
    Filed: September 27, 1996
    Date of Patent: March 9, 1999
    Assignee: California Institute of Technology
    Inventors: Mark W. Grinstaff, Harry B. Gray, Thomas J. Meade
  • Patent number: 5859214
    Abstract: Compounds of general formula I ##STR1## wherein Z.sup.1, Z.sup.2, X, R.sup.2 and R.sup.3 are as herein defined, are valuable pharmaceutical agents. In particular, the compounds are useful as contrast agents in NMR diagnosis.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: January 12, 1999
    Assignee: Schering Aktiengesellshaft
    Inventors: Heinz Gries, Erich Klieger, Bernd Raduchel, Heribert Schmitt-Willich, Hanns-Joachim Weinmann, Hubert Vogler, Gabriele Schuhmann-Giampieri, Jurgen Conrad
  • Patent number: 5854363
    Abstract: An (omega-alkenyl) (cyclopentacarbyl) metallocene compound is provided. Polymerization processes therewith are also provided.
    Type: Grant
    Filed: November 24, 1997
    Date of Patent: December 29, 1998
    Assignee: Phillips Petroleum Company
    Inventors: Michael Jung, Helmut G. Alt, M. Bruce Welch
  • Patent number: 5792793
    Abstract: The present invention relates to a complex formed by the coordination between a thiol group-containing compound and a silver ion; an antibacterial, antifungal, and antiviral agent containing the same as the active agent; and an antibacterial, antifungal, and antiviral composition containing the above agent and a vehicle or a carrier.The agent has a wide antibacterial and antifungal spectrum and an antiviral activity, is well compatible with various vehicles and carriers, sustains its activity for long, and has reduced peroral toxicity, skin irritation and mucosa irritation.
    Type: Grant
    Filed: May 6, 1996
    Date of Patent: August 11, 1998
    Assignees: Meiji Milk Products Co., Ltd., Toyo Ink Mfg. Co., Ltd.
    Inventors: Munehiro Oda, Hiroyuki Itoh, Tetsushi Sudo, Sadatoshi Sakuma, Kenji Nomiya, Yasunori Suzuki, Yukiyoshi Jonoshita, Akira Kikuchi, Yoshiko Takabatake
  • Patent number: 5767301
    Abstract: A method is provided for applying chemical vapor deposition (CVD) copper (Cu) to integrated circuit substrates using a Cu(hfac)(ligand) precursor with a silylolefin ligand including combinations of C1-C8 alkyl groups with at least one C2-C8 alkyloxy group. The alkyloxy groups include, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and aryloxy, while the alkyl groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, and aryl. The oxygen atoms of the alkyloxy groups, and the long carbon chains of both the alkyl and alkyloxy groups, increase the stability of the precursor by contributing electrons to the Cu(hfac) complex. The improved bond helps insure that the ligand separates from the (hfac)Cu complex at consistent temperatures when Cu is to be deposited. Combinations of alkyloxy and alkyl groups allow the molecular weight of the precursor to be manipulated so that the volatility of the precursor is adjustable for specific process scenarios.
    Type: Grant
    Filed: January 21, 1997
    Date of Patent: June 16, 1998
    Assignees: Sharp Microelectronics Technology, Inc., Sharp Kabushiki Kaisha
    Inventors: Yoshihide Senzaki, Masato Kobayashi, Lawrence J. Charneski, Tue Nguyen
  • Patent number: 5688981
    Abstract: Silver chelating agent and surfactant that exhibits photosensitivity and antimicrobial activity. The silver can be chelated with ethylenediaminetriacetic acid (ED3A) or salts thereof, or preferably with N-acyl ED3A or salts thereof. Antimicrobial activity is exhibited even at very low silver levels.
    Type: Grant
    Filed: November 21, 1996
    Date of Patent: November 18, 1997
    Assignee: Hampshire Chemical Corp.
    Inventor: Arthur M. Nonomura
  • Patent number: 5681543
    Abstract: Polymers comprising a ligand containing a carboxylic acid group, optionally at least one ion of an element of the atomic numbers 21-29, 42, 44 or 57-83 as well as optionally cations of inorganic and/or organic bases, amino acids or amino acid amides are valuable complexing agents and complexes for diagnosis.
    Type: Grant
    Filed: August 10, 1994
    Date of Patent: October 28, 1997
    Assignee: Shering Aktiengesellschaft
    Inventors: Heribert Schmitt-Willich, Julius Deutsch, Heinz Gries, Jurgen Conrad, Reinhard Neumeier