Patents by Inventor Masashi Sugiya

Masashi Sugiya has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 8957233
    Abstract: An industrially advantageous method for producing an optically active 1,2-bis(dialkylphosphino)benzene derivative of the present invention is provided. The method is characterized in that a phosphine-borane compound represented by the following general formula (1) is subjected to a deboronation reaction, followed by lithiation, then the reaction product is subjected to reaction with an alkyldihalogenophosphine represented by RaPX?2, and thereafter the reaction product is subjected to reaction with a Grignard reagent represented by RbMgX? to produce an optically active 1,2-bis(dialkylphosphino)benzene derivative (A). R1 and R2 respectively represent an alkyl group having 1 to 8 carbon atoms, and the number of carbon atoms is different between R1 and R2. Ra is either R1 or R2 and Rb is the other of R1 and R2. X, X?, and X? each represent a halogen atom.
    Type: Grant
    Filed: July 3, 2011
    Date of Patent: February 17, 2015
    Assignee: Nippon Chemical Industrial Co., Ltd.
    Inventors: Ken Tamura, Masashi Sugiya, Tsuneo Imamoto
  • Publication number: 20130172597
    Abstract: An industrially advantageous method for producing an optically active 1,2-bis(dialkylphosphino)benzene derivative of the present invention is provided. The method is characterized in that a phosphine-borane compound represented by the following general formula (1) is subjected to a deboronation reaction, followed by lithiation, then the reaction product is subjected to reaction with an alkyldihalogenophosphine represented by RaPX?2, and thereafter the reaction product is subjected to reaction with a Grignard reagent represented by RbMgX? to produce an optically active 1,2-bis(dialkylphosphino)benzene derivative (A). R1 and R2 respectively represent an alkyl group having 1 to 8 carbon atoms, and the number of carbon atoms is different between R1 and R2. Ra is either R1 or R2 and Rb is the other of R1 and R2. X, X?, and X? each represent a halogen atom.
    Type: Application
    Filed: July 3, 2011
    Publication date: July 4, 2013
    Applicant: NIPPON CHEMICAL INDUSTRIAL CO., LTD.
    Inventors: Ken Tamura, Masashi Sugiya, Tsuneo Imamoto
  • Patent number: 8198471
    Abstract: A novel phosphine compound capable of forming a metal complex useful as a catalyst for various asymmetric synthesis reactions, a production method thereof, and a metal complex comprising the aforementioned compound as a ligand.
    Type: Grant
    Filed: March 8, 2010
    Date of Patent: June 12, 2012
    Assignee: Nippon Chemical Industrial Co., Ltd.
    Inventors: Ken Tamura, Masashi Sugiya, Tsuneo Imamoto
  • Patent number: 8114212
    Abstract: Powdery silica composite particles obtained by a surface treatment step of adding acid or alkali to a reactant solution comprising: core silica particles of 5 to 200 nm in average particle size; alkoxysilane; a phosphonium salt ionic liquid represented by general formula (1); wherein R1, R2, and R3 respectively represent a linear or branched alkyl group having 1 to 5 carbon atoms, R4 represents a linear or branched alkyl group having 1 to 5 carbon atoms, n represents an integer of 1 to 8, and X represents an anionic group; and a reaction solvent such that the alkoxysilane is hydrolyzed, thereby surface-treating the core silica particles.
    Type: Grant
    Filed: February 6, 2009
    Date of Patent: February 14, 2012
    Assignees: Nippon Chemical Industrial Co., Ltd., National University Corporation Hirosaki University
    Inventors: Hideo Sawada, Katsuhiko Tsunashima, Masashi Sugiya
  • Publication number: 20100267980
    Abstract: An object of the present invention is to provide a deep-ultraviolet-transmitting epoxy resin cured product having high heat resistance and high resistance to deep-ultraviolet light, and to provide a curing accelerator and an epoxy resin composition which are used for producing the epoxy resin cured product. The curing accelerator for deep-ultraviolet-transmitting epoxy resins comprises a tetraalkylphosphonium dialkyl phosphate represented by the following general formula (1): wherein R1, R2, R3, R4, R5, and R6 each represent an alkyl group or an alkyl group having a hydroxyl group, which has 1 to 8 carbon atoms and is linear, branched, or alicyclic; and R1, R2, R3, R4, R5, and R6 may be the same or different. Also disclosed are an epoxy resin composition comprising the curing accelerator and an epoxy resin cured product obtained by curing the resin composition.
    Type: Application
    Filed: May 18, 2010
    Publication date: October 21, 2010
    Applicant: NIPPON CHEMICAL INDUSTRIAL CO., LTD.
    Inventors: Katsuhiko TSUNASHIMA, Masashi SUGIYA
  • Publication number: 20100234626
    Abstract: It is an object of the present invention to provide a novel phosphine compound capable of forming a metal complex useful as a catalyst for various asymmetric synthesis reactions, a production method thereof, and a metal complex comprising the aforementioned compound as a ligand. A 2,2?-bis(dialkylphosphino)biphenyl compound represented by the formula (A-1). A compound represented by the formula (1) is appropriate as a catalyst for an asymmetric synthesis reaction. The biphenyl compound represented by the formula (A-1) can be obtained by subjecting a compound represented by the formula (A-2) to a coupling reaction to obtain an intermediate represented by the formula (A-3), and then subjecting the intermediate to a deboranation reaction. In the formula (A-1), R1 and R2 each independently represent a C1-C10 alkyl group, R3 represents a monovalent substituent, and n represents an integer of 0 to 4.
    Type: Application
    Filed: March 8, 2010
    Publication date: September 16, 2010
    Applicant: NIPPON CHEMICAL INDUSTRIAL CO., LTD.
    Inventors: Ken Tamura, Masashi Sugiya, Tsuneo Imamoto
  • Publication number: 20090203820
    Abstract: It is intended to provide highly dispersible, powdery silica composite particles comprising a phosphonium salt ionic liquid immobilized in the surface and comprising the ionic liquid at a high content. It is also intended to provide an industrially advantageous process for producing the powdery silica composite particles at high yields. The present invention provides powdery silica composite particles obtained by a surface treatment step of adding acid or alkali to a reactant solution comprising: core silica particles of 5 to 200 nm in average particle size; alkoxysilane; a phosphonium salt ionic liquid represented by the following general formula (1); and a reaction solvent such that the alkoxysilane is hydrolyzed, thereby surface-treating the core silica particles.
    Type: Application
    Filed: February 6, 2009
    Publication date: August 13, 2009
    Applicants: NIPPON CHEMICAL INDUSTRIAL CO., LTD., NATIONAL UNIVERSITY CORPORATION HIROSAKI UNIVERSITY
    Inventors: Hideo SAWADA, Katsuhiko TSUNASHIMA, Masashi SUGIYA
  • Publication number: 20090118442
    Abstract: An object of the present invention is to provide a deep-ultraviolet-transmitting epoxy resin cured product having high heat resistance and high resistance to deep-ultraviolet light, and to provide a curing accelerator and an epoxy resin composition which are used for producing the epoxy resin cured product. The curing accelerator for deep-ultraviolet-transmitting epoxy resins comprises a tetraalkylphosphonium dialkyl phosphate represented by the following general formula (1): wherein R1, R2, R3, R4, R5, and R6 each represent an alkyl group or an alkyl group having a hydroxyl group, which has 1 to 8 carbon atoms and is linear, branched, or alicyclic; and R1, R2, R3, R4, R5, and R6 may be the same or different. Also disclosed are an epoxy resin composition comprising the curing accelerator and an epoxy resin cured product obtained by curing the resin composition.
    Type: Application
    Filed: April 13, 2007
    Publication date: May 7, 2009
    Applicant: NIPPON CHEMICAL INDUSTRIAL CO., LTD.
    Inventors: Katsuhiko Tsunashima, Masashi Sugiya
  • Publication number: 20090069472
    Abstract: The antistatic agent for resins of the present invention contains phosphonium salts represented by the general formula (1) below: (wherein R1, R2, and R3 are each a straight-chain or branched alkyl group having 3 to 8 carbon atoms, and R4 is a straight-chain or branched alkyl group having 10 to 22 carbon atoms; each alkyl group may have substituted hydroxy group or alkoxy group; R1, R2, and R3 may be the same or different from each another; and X? is a tetrafluoroborate ion or a hexafluorophosphate ion).
    Type: Application
    Filed: October 15, 2008
    Publication date: March 12, 2009
    Applicant: NIPPON CHEMICAL INDUSTRIAL CO., LTD.
    Inventors: Hiroshi Kawakabe, Masashi Sugiya, Yoshifusa Hara, Shigeyuki Arai, Jin Saimaru
  • Publication number: 20090047518
    Abstract: An object of the invention is to provide a substance enabling uniformly dispersing an ionic liquid or a phosphonium salt in various solvents, resin materials, and the like. A powdery silica composite particle obtained by a surface treatment step comprising providing a reaction solution by mixing a silica sol containing a core silica particle having an average particle size of 5 to 200 nm, an alkoxysilane, and an ionic liquid and hydrolyzing the alkoxysilane by addition of an acid or an alkali to the reaction solution to surface-treat the core silica particle.
    Type: Application
    Filed: March 6, 2007
    Publication date: February 19, 2009
    Applicants: NIPPON CHEMICAL INDUSTRIAL CO., LTD., NATIONAL UNIVERSITY CORPORATION HIROSAKI UNIVERSIT Y
    Inventors: Hideo Sawada, Masashi Sugiya, Ryo Ebara, Katsuhiko Tsunashima
  • Publication number: 20090036599
    Abstract: A material enabling uniformly dispersing an ionic liquid or a phosphonium salt in various solvents or resin materials is provided. The material is powdery particles of a three-dimensionally crosslinked clathrate obtained by a process including a first-order polymerization step in which a fluoroalkanoyl peroxide compound, a monofunctional monomer, and a polyfunctional monomer having an olefinic double bond and an isocyanate group are reacted to one another to obtain a fluoroalkyl-containing cooligomer and a crosslinking step including the substeps of mixing the fluoroalkyl-containing cooligomer and an ionic liquid or a phosphonium salt and causing the cooligomer to react with itself at the isocyanate groups thereof in the presence of the ionic liquid or the phosphonium salt to obtain powdery three-dimensionally crosslinked clathrate particles.
    Type: Application
    Filed: March 16, 2007
    Publication date: February 5, 2009
    Applicants: NIPPON CHEMICAL INDUSTRIAL CO., LTD., NATIONAL UNIVERSITY CORPORATION HIROSAKI UNIVERSITY
    Inventors: Hideo Sawada, Masashi Sugiya, Ryo Ebara
  • Publication number: 20060100326
    Abstract: The antistatic agent for resins of the present invention contains phosphonium salts represented by the general formula (1) below: (wherein R1, R2, and R3 are each a straight-chain or branched alkyl group having 3 to 8 carbon atoms, and R4 is a straight-chain or branched alkyl group having 10 to 22 carbon atoms; each alkyl group may have substituted hydroxy group or alkoxy group; R1, R2, and R3 may be the same or different from each another; and X? is a tetrafluoroborate ion or a hexafluorophosphate ion).
    Type: Application
    Filed: December 19, 2003
    Publication date: May 11, 2006
    Applicants: NIPPPON CHEMICAL INDUSTRIAL CO., LTD, NAGASE & CO. LTD
    Inventors: Hiroshi Kawakabe, Masashi Sugiya, Yoshifusa Hara, Shigeyuki Arai, Jim Saimaru
  • Patent number: 6649728
    Abstract: A catalyst for curing epoxy resins comprises a tetraalkylphosphonium tetrafluoroborate represented by Formula (1): wherein R1, R2, R3, and R4 are each C1-C5 linear or branched alkyl and may be the same or different, and the halogen ion content in the tetraalkylphosphonium tetrafluoroborate is 20 ppm or less. An epoxy resin powder coating composition containing this catalyst exhibits a prolonged pot life and can be baked at decreased temperatures.
    Type: Grant
    Filed: July 3, 2002
    Date of Patent: November 18, 2003
    Assignee: Nippon Chemical Industrial Co., Ltd.
    Inventors: Hiroshi Kawakabe, Masashi Sugiya, Yoshifusa Hara
  • Patent number: 6603032
    Abstract: The present invention provides a novel bisphosphine compound having a chiral center on the phosphorus atom, which is suitable as a ligand for an asymmetric catalyst for use in asymmetric hydrogenation, this bisphosphine compound being represented by the following formula (1): (where t—C8H17 denotes 1,1,3,3-tetramethylbutyl), and a process for the production of this bisphosphine compound. Also provided are a transition metal complex having this bisphosphine compound as a ligand, and a process for the asymmetric hydrogenation of an unsubstituted carboxylic acid or its ester.
    Type: Grant
    Filed: June 18, 2002
    Date of Patent: August 5, 2003
    Assignee: Nippon Chemical Industries Co., Ltd.
    Inventors: Masashi Sugiya, Hiroyuki Nohira
  • Publication number: 20030109378
    Abstract: A catalyst for curing epoxy resins comprises a tetraalkylphosphonium tetrafluoroborate represented by Formula (1): 1
    Type: Application
    Filed: July 3, 2002
    Publication date: June 12, 2003
    Inventors: Hiroshi Kawakabe, Masashi Sugiya, Yoshifusa Hara
  • Patent number: 6214196
    Abstract: A method of producing a bisphosphine oxide by performing a koble electrolysis coupling reaction to a phosphine oxide carboxylic acid represented by the general formula (1): wherein the bisphosphine oxide is represented by the following general formula (2):
    Type: Grant
    Filed: August 9, 1999
    Date of Patent: April 10, 2001
    Assignee: Nippon Chemical Industrial Co., Ltd.
    Inventors: Masashi Sugiya, Hiroyuki Nohira
  • Patent number: 6177591
    Abstract: An optically active 1-phenylethylamine is reacted to a phosphine oxide carboxylic acid of a racemic modification shown by the following general formula (2): and a produced diastereomeric salt is separated using the difference in solubility against a solvent, which is subsequently decomposed by acid, so as to free and separate an optically active phosphine oxide carboxylic acid.
    Type: Grant
    Filed: August 10, 1999
    Date of Patent: January 23, 2001
    Assignee: Nippon Chemical Industrial Co., Ltd.
    Inventors: Masashi Sugiya, Hiroyuki Nohira
  • Patent number: 6121494
    Abstract: Reacting a lead tetraacetate with an optically active phosphine oxide carboxylic acid represented by the following general formula (1): ##STR1## in order to obtain an optically active vinyl phosphine oxide represented by the following general formula (2): ##STR2##
    Type: Grant
    Filed: December 9, 1999
    Date of Patent: September 19, 2000
    Assignee: Nippon Chemical Industrial Co., Ltd.
    Inventors: Masashi Sugiya, Hiroyuki Nohira
  • Patent number: 6080885
    Abstract: A phosphonium salt compound having an acryl group which is represented by the following general formula (3) can be made in simple operations: ##STR1## (wherein A represents a alkylene group, Y represents Cl, Br or I, R.sup.1 represents H or CH.sub.3, and R.sup.2, R.sup.3 and R.sup.4 represent a alkyl group having 1-8 carbon atoms, cycloalkyl, aryl, alkaryl or aralkyl group) by reacting an unsaturated aliphatic carboxylic acid halide of the following general formula (1):CH.sub.2 .dbd.CR.sup.1 --COX (1)(wherein R.sup.1 represents H or CH.sub.3 and X represents Cl, Br or I) with a hydroxyalkyl phosphonium salt compound of the following general formula (2):[HO--A--P.sup.+ R.sup.2 R.sup.3 R.sup.4 ]Y.sup.- (2)(wherein A, Y, R.sup.2, R.sup.3 and R.sup.4 have the same meanings as defined above). The present invention is industrially advantageous since the product can have a very high purity and be obtained in high yield by an easy operation.
    Type: Grant
    Filed: September 15, 1998
    Date of Patent: June 27, 2000
    Assignee: Nippon Chemical Industrial Co., Ltd.
    Inventors: Masashi Sugiya, Tsutomu Watanabe
  • Patent number: 6025525
    Abstract: A highly pure monoalkylphosphine which is useful as a starting material for producing a compound semiconductor, and a method for producing same in high yield are provided. The highly pure monoalkylphosphine is represented by the general formula RPH.sub.2 (wherein R is an alkyl group having 1 to 8 carbon atoms), has a purity of not less than 99.999%, and is substantially free of sulfur and silica. In the method of producing said highly pure monoalkylphosphine, anhydrous hydrofluoric acid is used as a catalyst for a reaction between phosphine and an alkene, and the reaction is carried out in the presence of an organic solvent having a boiling point higher than that of the resulting monoalkylphosphine; the resulting reaction mixture is contacted with an alkali solution so that the remaining catalyst is removed into an aqueous phase in the form of a fluoride salt; next, the obtained reaction mixture is contacted with an alkali hydride and the impurities are removed, then distillation is carried out.
    Type: Grant
    Filed: December 21, 1998
    Date of Patent: February 15, 2000
    Assignees: Nippon Chemical Industrial Co., Ltd., Shin-Etsu Chemical Co., Ltd.
    Inventors: Masashi Sugiya, Tsutomu Watanabe, Natsuhiro Sano