Patents by Inventor Makoto Tsubuku

Makoto Tsubuku 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: 10160824
    Abstract: The cyanate ester compound of the present invention is obtained by cyanating a modified naphthalene formaldehyde resin.
    Type: Grant
    Filed: June 16, 2014
    Date of Patent: December 25, 2018
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Masayuki Katagiri, Go Higashihara, Kenji Arii, Yuuichi Sugano, Makoto Tsubuku
  • Patent number: 9949369
    Abstract: The present invention is a cyanate ester compound represented by the following formula (1): wherein Ar represents an aromatic ring; R1 each independently represents a hydrogen atom, an alkyl group, or an aryl group; n each independently represents an integer of 1 to 3; m+n is the same as the total number of hydrogen atoms in a monovalent aromatic group containing the aromatic ring and the hydrogen atoms; R2 represents a hydrogen atom (excluding a case where Ar represents a benzene ring; n each represents 1; R1 represents a hydrogen atom; m each represents 4, and a cyanate group is bonded to the benzene ring in the 4-position relative to an adamantyl group), or an alkyl group having 1 to 4 carbon atoms; and R3 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
    Type: Grant
    Filed: October 24, 2014
    Date of Patent: April 17, 2018
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Masayuki Katagiri, Keita Tokuzumi, Makoto Tsubuku, Tomoo Tsujimoto, Kenji Arii, Takashi Kobayashi, Masanobu Sogame, Yoshinori Mabuchi, Sotaro Hiramatsu
  • Patent number: 9657173
    Abstract: A curable resin composition which can achieve a cured product in which the generation of cracks upon curing is suppressed and which has both a low thermal expansion rate and a low water absorbability is provided. The curable resin composition comprises: at least a cyanate ester compound (A) represented by the following formula (I); a metal complex catalyst (B); and an additive (C), wherein the additive (C) contains any one or more selected from the group consisting of a compound represented by the following general formula (II), a compound represented by the following general formula (III), and a tertiary amine.
    Type: Grant
    Filed: January 31, 2012
    Date of Patent: May 23, 2017
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Makoto Tsubuku, Taketo Ikeno, Masayuki Katagiri, Tomoo Tsujimoto
  • Patent number: 9475761
    Abstract: A method for efficiently producing a cyanogen halide with suppressed side effects, and a method for producing a high-purity cyanate ester compound at a high yield includes contacting a halogen molecule with an aqueous solution containing hydrogen cyanide and/or a metal cyanide, so that the hydrogen cyanide and/or the metal cyanide is allowed to react with the halogen molecule in the reaction solution to obtain the cyanogen halide, wherein more than 1 mole of the hydrogen cyanide or the metal cyanide is used based on 1 mole of the halogen molecule, and when an amount of substance of an unreacted hydrogen cyanide or an unreacted metal cyanide is defined as mole (A) and an amount of substance of the generated cyanogen halide is defined as mole (B), the reaction is terminated in a state in which (A):(A)+(B) is between 0.00009:1 and 0.2:1.
    Type: Grant
    Filed: October 25, 2013
    Date of Patent: October 25, 2016
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Masayuki Katagiri, Yuuichi Sugano, Taketo Ikeno, Makoto Tsubuku, Keita Tokuzumi, Kenj Arii, Takashi Kobayashi, Masanobu Sogame, Yoshinori Mabuchi, Yoshihiro Kato
  • Patent number: 9453126
    Abstract: There is provided a novel dicyanatophenyl-based difunctional cyanate ester which is in a liquid form at ordinary temperature and can obtain a cured product having an excellent low thermal expansion rate. There is disclosed a cyanate ester compound represented by the following formula (I): (wherein R1 represents a hydrocarbon group having 2 to 20 carbon atoms).
    Type: Grant
    Filed: October 25, 2011
    Date of Patent: September 27, 2016
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Makoto Tsubuku, Taketo Ikeno, Masayuki Katagiri, Tomoo Tsujimoto
  • Publication number: 20160262263
    Abstract: The present invention is a cyanate ester compound represented by the following formula (1): wherein Ar represents an aromatic ring; R1 each independently represents a hydrogen atom, an alkyl group, or an aryl group; n each independently represents an integer of 1 to 3; m+n is the same as the total number of hydrogen atoms in a monovalent aromatic group containing the aromatic ring and the hydrogen atoms; R2 represents a hydrogen atom (excluding a case where Ar represents a benzene ring; n each represents 1; R1 represents a hydrogen atom; m each represents 4, and a cyanate group is bonded to the benzene ring in the 4-position relative to an adamantyl group), or an alkyl group having 1 to 4 carbon atoms; and R3 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
    Type: Application
    Filed: October 24, 2014
    Publication date: September 8, 2016
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Masayuki KATAGIRI, Keita TOKUZUMI, Makoto TSUBUKU, Tomoo TSUJIMOTO, Kenji ARII, Takashi KOBAYASHI, Masanobu SOGAME, Yoshinori MABUCHI, Sotaro HIRAMATSU
  • Publication number: 20160115271
    Abstract: The cyanate ester compound of the present invention is obtained by cyanating a modified naphthalene formaldehyde resin.
    Type: Application
    Filed: June 16, 2014
    Publication date: April 28, 2016
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Masayuki KATAGIRI, Go HIGASHIHARA, Kenji ARII, Yuuichi SUGANO, Makoto TSUBUKU
  • Publication number: 20150299110
    Abstract: A method for efficiently producing a cyanogen halide with suppressed side effects, and a method for producing a high-purity cyanate ester compound at a high yield includes contacting a halogen molecule with an aqueous solution containing hydrogen cyanide and/or a metal cyanide, so that the hydrogen cyanide and/or the metal cyanide is allowed to react with the halogen molecule in the reaction solution to obtain the cyanogen halide, wherein more than 1 mole of the hydrogen cyanide or the metal cyanide is used based on 1 mole of the halogen molecule, and when an amount of substance of an unreacted hydrogen cyanide or an unreacted metal cyanide is defined as mole (A) and an amount of substance of the generated cyanogen halide is defined as mole (B), the reaction is terminated in a state in which (A):(A)+(B) is between 0.00009:1 and 0.2:1.
    Type: Application
    Filed: October 25, 2013
    Publication date: October 22, 2015
    Inventors: Masayuki KATAGIRI, Yuuichi SUGANO, Taketo IKENO, Makoto TSUBUKU, Keita TOKUZUMI, Kenj ARII, Takashi KOBAYASHI, Masanobu SOGAME, Yoshinori MABUCHI, Yoshihiro KATO
  • Publication number: 20140242394
    Abstract: A curable resin composition which is in a liquid form at ordinary temperature and provides a cured product having excellent heat resistance and a low thermal expansion rate is provided. The curable resin composition according to the present invention comprises: a cyanate ester compound (A) represented by the following formula (I); and a curing accelerator (B): wherein R1 represents a hydrocarbon group having 2 to 20 carbon atoms.
    Type: Application
    Filed: July 2, 2012
    Publication date: August 28, 2014
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Makoto Tsubuku, Taketo Ikeno, Masayuki Katagiri, Yuuichi Sugano
  • Patent number: 8779162
    Abstract: There is provided a novel cyanate ester compound that can provide a cured product possessing excellent heat resistance. The cyanate ester compound is represented by general formula (1): wherein R1 represents an aromatic substituent having 6 to 10 carbon atoms or an alkyl group having 1 to 20 carbon atoms; Rx1's each independently represent a hydrogen atom, an alkyl or alkoxy group having 1 to 20 carbon atoms, or a halogen; Ry1's each independently represent a hydrogen atom, an alkyl or alkoxy group having 1 to 20 carbon atoms, or a halogen; m is an integer of 0 to 4; and n is an integer of 0 to 4.
    Type: Grant
    Filed: January 18, 2011
    Date of Patent: July 15, 2014
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Taketo Ikeno, Makoto Tsubuku, Masayuki Katagiri, Tomoo Tsujimoto
  • Publication number: 20130288063
    Abstract: A curable resin composition which can achieve a cured product in which the generation of cracks upon curing is suppressed and which has both a low thermal expansion rate and a low water absorbability is provided. The curable resin composition comprises: at least a cyanate ester compound (A) represented by the following formula (I); a metal complex catalyst (B); and an additive (C), wherein the additive (C) contains any one or more selected from the group consisting of a compound represented by the following general formula (II), a compound represented by the following general formula (III), and a tertiary amine.
    Type: Application
    Filed: January 31, 2012
    Publication date: October 31, 2013
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Makoto Tsubuku, Taketo Ukeno, Masayuki Katagiri, Tomoo Tsujimoto
  • Publication number: 20130281640
    Abstract: There is provided a novel dicyanatophenyl-based difunctional cyanate ester which is in a liquid form at ordinary temperature and can obtain a cured product having an excellent low thermal expansion rate. There is disclosed a cyanate ester compound represented by the following formula (I): (wherein R1 represents a hydrocarbon group having 2 to 20 carbon atoms).
    Type: Application
    Filed: October 25, 2011
    Publication date: October 24, 2013
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Makoto Tsubuku, Taketo Ikeno, Masayuki Katagiri, Tomoo Tsujimoto
  • Publication number: 20130023640
    Abstract: There is provided a novel cyanate ester compound that can provide a cured product possessing excellent heat resistance. The cyanate ester compound is represented by general formula (1): wherein R1 represents an aromatic substituent having 6 to 10 carbon atoms or an alkyl group having 1 to 20 carbon atoms; Rx1's each independently represent a hydrogen atom, an alkyl or alkoxy group having 1 to 20 carbon atoms, or a halogen; Ry1's each independently represent a hydrogen atom, an alkyl or alkoxy group having 1 to 20 carbon atoms, or a halogen; m is an integer of 0 to 4; and n is an integer of 0 to 4.
    Type: Application
    Filed: January 18, 2011
    Publication date: January 24, 2013
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Taketo Ikeno, Makoto Tsubuku, Masayuki Katagiri, Tomoo Tsujimoto