Patents by Inventor Hidefumi Harada

Hidefumi Harada 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).

  • Publication number: 20190382345
    Abstract: Provided is a method for regenerating an aromatic amide compound into a corresponding aromatic nitrile compound, the method realizing a dehydration reaction of providing a target compound selectively at a high yield, with generation of a by-product being suppressed. Also provided is a method for producing an aromatic nitrile compound that decreases the number of steps of the dehydration reaction and significantly improves the reaction speed even at a pressure close to normal pressure. In addition, the above-described production method is applied to a carbonate ester production method to provide a method for producing a carbonate ester efficiently. The above-described methods are realized by a method for producing an aromatic nitrile compound including a dehydration reaction of dehydrating an aromatic amide compound, in which the dehydration reaction uses, as a solvent, any of 1,2-dimethoxybenzene, 1,3-dimethoxybenzene and 1,3,5-trimethoxybenzene.
    Type: Application
    Filed: November 30, 2017
    Publication date: December 19, 2019
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Hidefumi HARADA, Yousuke SHINKAI, Hongyu LIU, Takehiko ISOBE, Yoshinori ISAHAYA
  • Publication number: 20190185408
    Abstract: Provided is a method for regenerating an aromatic amide compound into a corresponding aromatic nitrile compound, the method realizing a dehydration reaction of providing a target compound selectively at a high yield with generation of a by-product being suppressed. Also provided is a method for producing an aromatic nitrile compound that decreases the number of steps of dehydration reaction and significantly improves the reaction speed at a pressure close to normal pressure. Furthermore, the above-described production method is applied to a carbonate ester production method to provide a method for producing carbonate ester efficiently. The above-described objects are achieved by a method for producing an aromatic nitrile compound including a dehydration reaction of dehydrating an aromatic amide compound, in which the dehydration reaction uses diphenylether.
    Type: Application
    Filed: June 20, 2017
    Publication date: June 20, 2019
    Applicants: Mitsubishi Gas Chemical Company, Inc., Tohoku University, Nippon Steel & Sumitomo Metal Corporation, Nippon Steel & Sumikin Engineering Co., Ltd.
    Inventors: Yousuke SHINKAI, Hongyu LIU, Hidefumi HARADA, Yoshinori ISAHAYA, Keiichi TOMISHIGE, Yoshinao NAKAGAWA, Masazumi TAMURA, Kimihito SUZUKI, Yasuki NAMIKI
  • Publication number: 20190119441
    Abstract: A high molecular weight aromatic polycarbonate resin manufacturing method that can achieve good quality and sufficiently high molecular weight includes: a step in which a dialcohol compound expressed by general formula (1) and a catalyst are mixed to obtain a catalyst composition; a step in which the obtained catalyst composition is transferred to a prepolymer mixing tank via a transfer pipe; a step in which the transferred catalyst composition and an aromatic polycarbonate prepolymer are mixed in the prepolymer mixing tank, under a pressure that is greater than or equal to the vapor pressure of the dialcohol compound at the temperature of the prepolymer mixing tank and is less than or equal to 5 MPa, to obtain a prepolymer mixture; and a high molecular weight achievement step in which the obtained prepolymer mixture is heat-treated under reduced pressure conditions to obtain a high molecular weight aromatic polycarbonate resin.
    Type: Application
    Filed: March 24, 2017
    Publication date: April 25, 2019
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori ISAHAYA, Atsushi HIRASHIMA, Hidefumi HARADA, Maki ITO, Jun-ya HAYAKAWA, Takehiko ISOBE, Yousuke SHINKAI, Keisuke SHIMOKAWA
  • Publication number: 20190092901
    Abstract: Provided is a high molecular weight aromatic polycarbonate resin manufacturing method that suppresses the occurrence of heterogeneous structures and can achieve a sufficiently high molecular weight. A high molecular weight aromatic polycarbonate resin manufacturing method including: a step in which a dialcohol compound expressed by general formula (1) and a catalyst are mixed to obtain a catalyst composition; a step in which the obtained catalyst composition is transferred to a prepolymer mixing tank via a transfer pipe, with a transfer period of 10 hours or less; a step in which the transferred catalyst composition and an aromatic polycarbonate prepolymer are mixed in the prepolymer mixing tank to obtain a prepolymer mixture; and a high molecular weight achievement step in which the obtained prepolymer mixture is heat-treated under reduced pressure conditions to obtain a high molecular weight aromatic polycarbonate resin.
    Type: Application
    Filed: March 24, 2017
    Publication date: March 28, 2019
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori ISAHAYA, Atsushi HIRASHIMA, Hidefumi HARADA, Maki ITO, Jun-ya HAYAKAWA, Takehiko ISOBE, Yousuke SHINKAI, Keisuke SHIMOKAWA
  • Publication number: 20190085123
    Abstract: Provided is an aromatic polycarbonate resin composition with high fluidity, particularly during low shear, and a good color. An aromatic polycarbonate resin composition including: an aromatic polycarbonate resin that has a structural unit expressed by general formula (1); a aliphatic cyclic carbonate that is expressed by general formula (2) and is included at a ratio of 10 ppm-10,000 ppm; an aromatic cyclic carbonate that is expressed by general formula (3); and at least one compound selected from the group consisting of compounds expressed by general formulas (4)-(6), wherein the total content of the aromatic cyclic carbonate and the compound(s) expressed by general formula(s) (4)-(6) is 0.1 mass %-2.0 mass % by bisphenol A-converted value.
    Type: Application
    Filed: March 24, 2017
    Publication date: March 21, 2019
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori ISAHAYA, Atsushi HIRASHIMA, Hidefumi HARADA, Maki ITO, Jun-ya HAYAKAWA, Takehiko ISOBE, Yousuke SHINKAI, Keisuke SHIMOKAWA
  • Publication number: 20180290989
    Abstract: A diaryl carbonate containing a compound of the following formula (I) in an amount of less than 1,000 ppm by mass, and a method for producing the same: wherein R1 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, or an aryloxy group.
    Type: Application
    Filed: October 12, 2016
    Publication date: October 11, 2018
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Hidefumi HARADA, Jungo TAGUCHI, Yoshinori ISAHAYA
  • Patent number: 10053537
    Abstract: Copolymer having high fluidity and high molecular weight which is formed of a structural unit derived from an aliphatic diol compound and a structural unit derived from an aromatic dihydroxy compound. A polycarbonate resin composition is also provided comprising a highly polymerized aromatic polycarbonate resin as a main component and also comprising cyclic carbonate present in an amount of not more than 3000 ppm, wherein the highly polymerized aromatic polycarbonate resin is produced by a process which comprises a highly-polymerizing process wherein an aromatic polycarbonate is reacted with an aliphatic diol compound in the presence of a transesterification catalyst to increase the molecular weight.
    Type: Grant
    Filed: April 21, 2016
    Date of Patent: August 21, 2018
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori Isahaya, Atsushi Hirashima, Hidefumi Harada, Maki Ito, Jun-ya Hayakawa, Takehiko Isobe, Taichi Tokutake, Yousuke Shinkai
  • Patent number: 9822218
    Abstract: The present invention is to provide a process for producing a high molecular-weight aromatic polycarbonate resin, the process includes mixing a dialcohol compound represented by the following Formula (1) with a first catalyst to obtain a catalyst composition; mixing the obtained catalyst composition with an aromatic polycarbonate prepolymer to obtain a prepolymer mixture; and obtaining a high molecular-weight aromatic polycarbonate by subjecting the obtained prepolymer mixture to heating treatment under reduced pressure condition. In the Formula (1), R1 to R4 each independently represent a hydrogen atom, an alkyl group and the like. Q represents a divalent group or a single bond.
    Type: Grant
    Filed: November 12, 2014
    Date of Patent: November 21, 2017
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori Isahaya, Atsushi Hirashima, Hidefumi Harada, Maki Ito, Jun-ya Hayakawa, Takehiko Isobe, Hongyu Liu, Hiroki Furuhashi, Yousuke Shinkai
  • Patent number: 9701788
    Abstract: The present invention provides a method for producing a branched aromatic polycarbonate resin that is molecular weight-increased, which comprises subjecting an aromatic polycarbonate prepolymer and a linking agent comprising a trifunctional or more of an aliphatic polyol compound to transesterification reaction in the presence of a transesterification catalyst under a reduced pressure condition.
    Type: Grant
    Filed: August 7, 2013
    Date of Patent: July 11, 2017
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori Isahaya, Atsushi Hirashima, Hidefumi Harada, Maki Ito, Jun-ya Hayakawa, Takehiko Isobe, Taichi Tokutake, Yousuke Shinkai
  • Publication number: 20170174833
    Abstract: The present inventions provide a novel polycarbonate copolymer having high fluidity and high molecular weight which is formed of a structural unit derived from an aliphatic diol compound and a structural unit derived from an aromatic dihydroxy compound, having a structure represented by the formula (III): having the content of the structural unit derived from the aliphatic diol compound of 1-30 mol %, having the Q-value (280° C., 160 kg load) in the range from 0.02 to 1.0 ml/s, and having the weight average molecular weight (Mw) of 30,000 to 100,000, and an aromatic polycarbonate compound which is formed of a structural unit derived from an aromatic dihydroxy compound which is suitable for a prepolymer for producing a high fluidity polycarbonate copolymer.
    Type: Application
    Filed: March 1, 2017
    Publication date: June 22, 2017
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori ISAHAYA, Atsushi HIRASHIMA, Hidefumi HARADA, Maki ITO, Jun-ya HAYAKAWA, Takehiko ISOBE, Taichi TOKUTAKE, Yousuke SHINKAI
  • Patent number: 9546249
    Abstract: The present invention is to provide a process for preparing a highly polymerized aromatic polycarbonate resin, which comprises the steps of a highly polymerizing step for reacting an aromatic polycarbonate prepolymer and an aliphatic diol compound in the presence of a transesterification catalyst to obtain a highly polymerized aromatic polycarbonate resin, a cyclic carbonate removal step for removing at least part of the cyclic carbonate by-produced in the above highly polymerizing step out of the reaction system, and a recycle step of hydrolyzing the cyclic carbonate removed in the cyclic carbonate removal step to obtain an aliphatic diol compound and using the obtained aliphatic diol compound as at least a part of the aliphatic diol compound to be used in the highly polymerizing step.
    Type: Grant
    Filed: November 15, 2013
    Date of Patent: January 17, 2017
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori Isahaya, Atsushi Hirashima, Hidefumi Harada, Maki Ito, Jun-ya Hayakawa, Takehiko Isobe, Taichi Tokutake, Hongyu Liu, Yousuke Shinkai
  • Patent number: 9499661
    Abstract: The invention provides a process for producing a highly polymerized aromatic polycarbonate resin including a molecular weight-increasing step of reacting an aromatic polycarbonate prepolymer with an aliphatic diol compound represented by Formula (g2) in the presence of a transesterification catalyst to obtain a highly polymerized aromatic polycarbonate resin. In the formula, Ra and Rb each independently represent a hydrogen atom, a halogen atom, a linear or branched alkyl group, a cycloalkyl group, an aryl group or an alkoxy group, or Ra and Rb may be bonded to each other to form a ring; R1 to R4 each independently represent a hydrogen atom, a halogen atom or an alkyl group; and n represents an integer of 0 to 30.
    Type: Grant
    Filed: November 15, 2013
    Date of Patent: November 22, 2016
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori Isahaya, Atsushi Hirashima, Hidefumi Harada, Maki Ito, Jun-ya Hayakawa, Takehiko Isobe, Taichi Tokutake, Yousuke Shinkai
  • Patent number: 9458290
    Abstract: The present invention provides a process for preparing a highly polymerized aromatic polycarbonate resin which not only has excellent quality such that it has high molecular weight and high fluidity, but also has more excellent heat resistance. The process of the present invention comprises a highly polymerizing step for reacting an aromatic polycarbonate prepolymer with an aliphatic diol compound of the following formula (I) having hydroxymethyl groups (HO—CH2—) each bonded to a quaternary carbon atom in the presence of a transesterification catalyst to obtain a highly polymerized aromatic polycarbonate resin: wherein Ra to Rf, n, and m are as defined in the present specification and claims.
    Type: Grant
    Filed: November 15, 2013
    Date of Patent: October 4, 2016
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori Isahaya, Atsushi Hirashima, Hidefumi Harada, Maki Ito, Jun-ya Hayakawa, Takehiko Isobe, Taichi Tokutake, Yousuke Shinkai
  • Publication number: 20160272757
    Abstract: The present invention is to provide a process for producing a high molecular-weight aromatic polycarbonate resin, the process includes mixing a dialcohol compound represented by the following Formula (1) with a first catalyst to obtain a catalyst composition; mixing the obtained catalyst composition with an aromatic polycarbonate prepolymer to obtain a prepolymer mixture; and obtaining a high molecular-weight aromatic polycarbonate by subjecting the obtained prepolymer mixture to heating treatment under reduced pressure condition. In the Formula (1), R1 to R4 each independently represent a hydrogen atom, an alkyl group and the like. Q represents a divalent group or a single bond.
    Type: Application
    Filed: November 12, 2014
    Publication date: September 22, 2016
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori ISAHAYA, Atsushi HIRASHIMA, Hidefumi HARADA, Maki ITO, Jun-ya HAYAKAWA, Takehiko ISOBE, Hongyu LIU, Hiroki FURUHASHI, Yousuke SHINKAI
  • Publication number: 20160264726
    Abstract: The present inventions provide a novel polycarbonate copolymer having high fluidity and high molecular weight which is formed of a structural unit derived from an aliphatic diol compound and a structural unit derived from an aromatic dihydroxy compound, having a structure represented by the formula (III): having the content of the structural unit derived from the aliphatic diol compound of 1-30 mol %, having the Q-value (280° C., 160 kg load) in the range from 0.02 to 1.0 ml/s, and having the weight average molecular weight (Mw) of 30,000 to 100,000, and an aromatic polycarbonate compound which is formed of a structural unit derived from an aromatic dihydroxy compound which is suitable for a prepolymer for producing a high fluidity polycarbonate copolymer.
    Type: Application
    Filed: April 21, 2016
    Publication date: September 15, 2016
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori ISAHAYA, Atsushi HIRASHIMA, Hidefumi HARADA, Maki ITO, Jun-ya HAYAKAWA, Takehiko ISOBE, Taichi TOKUTAKE, Yousuke SHINKAI
  • Patent number: 9428608
    Abstract: The present invention provides an aromatic polycarbonate resin composition having a high molecular weight and less amount of a heterologous structure, retaining good qualities, and excellent in thermal stability, and an improved preparation process thereof.
    Type: Grant
    Filed: November 15, 2013
    Date of Patent: August 30, 2016
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori Isahaya, Atsushi Hirashima, Hidefumi Harada, Maki Ito, Jun-ya Hayakawa, Takehiko Isobe, Taichi Tokutake, Yousuke Shinkai
  • Patent number: 9353216
    Abstract: The present inventions provide processes for producing a highly polymerized aromatic polycarbonate resin comprising a highly-polymerizing process wherein an aromatic polycarbonate is reacted with an aliphatic diol compound represented by formula (g1) in the presence of a transesterification catalyst to increase the molecular weight: wherein Ra and Rb each independently represent a hydrogen atom, a linear or branched alkyl group having 1-12 carbon atoms or a phenyl group, and “m” represents an integer of 1-30.
    Type: Grant
    Filed: May 18, 2012
    Date of Patent: May 31, 2016
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori Isahaya, Atsushi Hirashima, Hidefumi Harada, Maki Ito, Jun-ya Hayakawa, Takehiko Isobe, Taichi Tokutake, Yousuke Shinkai
  • Patent number: 9243106
    Abstract: A high molecular weight polycarbonate resin is continuously produced by subjecting an aromatic polycarbonate prepolymer and an aliphatic diol compound to a linking and highly polymerizing reaction. Even an aliphatic diol compound having a comparatively low boiling point can be allowed to efficiently contribute to the linking and highly polymerizing reaction. An aromatic polycarbonate prepolymer is produced by a polycondensation reaction between an aromatic dihydroxy compound and a diester carbonate, adding an aliphatic diol compound having an aliphatic group bonding to a terminal hydroxyl group to obtain a prepolymer mixture, and subjecting the resulting prepolymer mixture to a linking and highly polymerizing reaction under reduced pressure.
    Type: Grant
    Filed: May 14, 2013
    Date of Patent: January 26, 2016
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori Isahaya, Atsushi Hirashima, Hidefumi Harada, Maki Ito, Jun-ya Hayakawa, Takehiko Isobe, Taichi Tokutake, Yousuke Shinkai
  • Publication number: 20150322203
    Abstract: The present invention provides a process for preparing a highly polymerized aromatic polycarbonate resin which not only has excellent quality such that it has high molecular weight and high fluidity, but also has more excellent heat resistance. The process of the present invention comprises a highly polymerizing step for reacting an aromatic polycarbonate prepolymer with an aliphatic diol compound of the following formula (I) having hydroxymethyl groups (HO—CH2—) each bonded to a quaternary carbon atom in the presence of a transesterification catalyst to obtain a highly polymerized aromatic polycarbonate resin: wherein Ra to Rf, n, and m are as defined in the present specification and claims.
    Type: Application
    Filed: November 15, 2013
    Publication date: November 12, 2015
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori ISAHAYA, Atsushi HIRASHIMA, Hidefumi HARADA, Maki ITO, Jun-ya HAYAKAWA, Takehiko ISOBE, Taichi TOKUTAKE, Yousuke SHINKAI
  • Publication number: 20150284509
    Abstract: The present invention provides an aromatic polycarbonate resin composition having a high molecular weight and less amount of a heterologous structure, retaining good qualities, and excellent in thermal stability, and an improved preparation process thereof.
    Type: Application
    Filed: November 15, 2013
    Publication date: October 8, 2015
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori Isahaya, Atsushi Hirashima, Hidefumi Harada, Maki Ito, Jun-ya Hayakawa, Takehiko Isobe, Taichi Tokutake, Yousuke Shinkai