Inorganic Sulfur Reactant Contains At Least One Metal Atom Or Contains An Ammonium Ion Patents (Class 528/388)
  • Patent number: 10501582
    Abstract: The present invention is to provide a method of producing polyarylene sulfide that can produce polyarylene sulfide having a low halogen content simply and easily and at low cost. The method of producing polyarylene sulfide according to an embodiment of the present invention includes: a preparation step of preparing a mixture containing an organic amide solvent, a sulfur source, a dihalo aromatic compound, and an alkali metal hydroxide; a first-stage polymerization step of producing a prepolymer until a pH of a reaction system reaches a range of lower than 10 but 7 or higher by initiating a polymerization reaction by heating the mixture; and a second-stage polymerization step of continuing the polymerization reaction.
    Type: Grant
    Filed: September 30, 2016
    Date of Patent: December 10, 2019
    Assignee: KUREHA CORPORATION
    Inventors: Akihiro Konno, Ken-Ichi Takaki, Hiroyuki Sato
  • Patent number: 10196487
    Abstract: The present invention is to provide a method of producing highly pure polyarylene sulfide (PAS) while the produced amount per unit volume is enhanced and side reactions are suppressed.
    Type: Grant
    Filed: September 30, 2016
    Date of Patent: February 5, 2019
    Assignee: KUREHA CORPORATION
    Inventors: Kenji Suzuki, Michihisa Miyahara, Hiroshi Sakabe
  • Patent number: 10138577
    Abstract: A poly(phenylene sulfide) fiber contains 1-10% by weight of a poly(phenylene sulfide) oligomer having a weight-average molecular weight of 5,000 or less, has a difference between a cold crystallization heat quantity (?Hc) and a crystal melting heat quantity (?Hm) during temperature rising in DSC, ?Hm??Hc, of 25 J/g or larger, and has an elongation of less than 40% and a strength of 3.0 cN/dtex or higher. The poly(phenylene sulfide) fiber has high heat resistance and chemical resistance and high strength and, despite this, has excellent suitability for high-order processing, e.g., thermal shapability, because the amorphous parts thereof have high molecular movability.
    Type: Grant
    Filed: May 22, 2015
    Date of Patent: November 27, 2018
    Assignee: Toray Industries, Inc.
    Inventors: Hiroo Katsuta, Takaaki Mihara, Daisuke Yamamoto, Shunsuke Horiuchi, Yoshitsugu Funatsu
  • Patent number: 9938379
    Abstract: Methods of forming a polyarylene sulfide and systems as may be utilized in carrying out the methods are described. Included in the formation method is a filtration process for treatment of a mixture, the mixture including a polyarylene sulfide, a salt byproduct of the polyarylene sulfide formation reaction, and a solvent. The filtration process includes maintaining the downstream side of the filter medium at an increased pressure. The downstream pressure can such that the boiling temperature of the mixture at the downstream pressure can be higher than the temperature at which the polyarylene sulfide is insoluble in the solvent.
    Type: Grant
    Filed: August 1, 2016
    Date of Patent: April 10, 2018
    Assignee: Ticona LLC
    Inventors: Hendrich Chiong, Michael Haubs, Damian Feord, Mark Shatzer, Jacob Grayson
  • Patent number: 9868824
    Abstract: A method for formation of a semi-crystalline polyarylene sulfide is described. The method can include reaction of sulfur-containing monomer with a dihaloaromatic monomer in an organic amide solvent to form a polymer following by combination of the polymer with a crystallization solution. The crystallization solution is pre-heated and the mixture formed is slowly cooled to crystallize the polymer.
    Type: Grant
    Filed: July 6, 2016
    Date of Patent: January 16, 2018
    Assignee: Ticona LLC
    Inventors: Hendrich Chiong, Michael Haubs, Damian Feord, Stanley Leonard, Jacob Grayson, Venkata Nekkanti
  • Patent number: 9765097
    Abstract: A method of producing a silane compound having a Formula (1) sulfonyl bond includes reacting a Formula (I) chlorosulfonyl compound with sodium sulfite in water as a solvent in the presence of a base, to produce a Formula (II) sulfinic acid sodium salt: and adding an aromatic hydrocarbon solvent to carry out azeotropic dehydration, and adding an aprotic polar solvent and a Formula (III) chloroalkylsilane compound. (wherein R1, R2, R3, R4, and R5 are each independently a substituent selected from a hydrogen atom, halogen atom, alkyl group, alkoxy group, haloalkyl group, haloalkoxy group, cyano group, and nitro group, R2 and R1 or R3 may form —CH?CH—CH?CH —together, R6 and R7 are each independently a C1-5 alkyl group, L is a single bond or saturated or unsaturated divalent C1-19 hydrocarbon group having a linear, branched, cyclic structure, or a combination thereof, and q is an integer of 1 to 3).
    Type: Grant
    Filed: June 17, 2015
    Date of Patent: September 19, 2017
    Assignee: NISSAN CHEMICAL INDUSTRIES, LTD.
    Inventor: Kenji Takase
  • Patent number: 9574013
    Abstract: Provided are antibodies that selectively bind to and inhibit activation of coagulation factor XII. Methods of treatment employing these antibodies are described herein.
    Type: Grant
    Filed: December 6, 2013
    Date of Patent: February 21, 2017
    Assignees: VANDERBILT UNIVERSITY, ARONORA, INC., OREGON HEALTH & SCIENCE UNIVERSITY
    Inventors: Andras Gruber, David Gailani, Philberta Leung, Anton Matafonov
  • Patent number: 9514889
    Abstract: Described is a process for the production of a capacitor, where an electrode body (1) of an electrode material (2) is provided, wherein a dielectric (3) covers one surface (4) of this electrode material (2) at least partly to form an anode body (5), where the in situ polymerization of at least one thiophene monomer in at least a part of the anode body (5) in the presence of at least one oxidizing agent and at least one polymer with the structural formula (I).
    Type: Grant
    Filed: March 11, 2013
    Date of Patent: December 6, 2016
    Assignee: Heraeus Precious Metals GmbH & Co. KG
    Inventors: Katrin Asteman, Udo Merker, Klaus Wussow
  • Patent number: 9403948
    Abstract: Methods of forming a polyarylene sulfide and systems as may be utilized in carrying out the methods are described. Included in the formation method is a filtration process for treatment of a mixture, the mixture including a polyarylene sulfide, a salt byproduct of the polyarylene sulfide formation reaction, and a solvent. The filtration process includes maintaining the downstream side of the filter medium at an increased pressure. The downstream pressure can such that the boiling temperature of the mixture at the downstream pressure can be higher than the temperature at which the polyarylene sulfide is insoluble in the solvent.
    Type: Grant
    Filed: September 9, 2014
    Date of Patent: August 2, 2016
    Assignee: Ticona LLC
    Inventors: Hendrich Chiong, Michael Haubs, Damian Feord, Mark Shatzer, Jacob Grayson
  • Patent number: 9388283
    Abstract: A method for formation of a semi-crystalline polyarylene sulfide is described. The method can include reaction of sulfur-containing monomer with a dihaloaromatic monomer in an organic amide solvent to form a polymer following by combination of the polymer with a crystallization solution. The crystallization solution is pre-heated and the mixture formed is slowly cooled to crystallize the polymer.
    Type: Grant
    Filed: September 9, 2014
    Date of Patent: July 12, 2016
    Assignee: Ticona LLC
    Inventors: Hendrich Chiong, Michael Haubs, Damian Feord, Stanley Leonard, Jacob Grayson, Venkata Nekkanti
  • Patent number: 9144925
    Abstract: Disclosed is a process for making shape memory polyphenylene sulfide, comprising: curing polyphenylene sulfide to produce cured polyphenylene sulfide; comminuting the cured polyphenylene sulfide to form cured polyphenylene sulfide particles; disposing the cured polyphenylene sulfide particles in a mold; heating the mold for flowing the cured polyphenylene sulfide; compressing, by applying a compressive force, the cured polyphenylene sulfide; cooling the cured polyphenylene sulfide; relieving the compressive force; and de-molding the cured polyphenylene sulfide to produce the shape memory polyphenylene sulfide.
    Type: Grant
    Filed: January 4, 2012
    Date of Patent: September 29, 2015
    Assignee: Baker Hughes Incorporated
    Inventors: Jiaxiang Ren, David P. Gerrard, James E. Goodson, Ping Duan, Gaurav Agrawal
  • Publication number: 20150126705
    Abstract: The present invention relates to a method for separating volatile substances, particularly iodine, diiodised aromatic compounds and/or mixtures thereof, from material mixtures containing said compounds. The invention further relates to a device for producing polyarylene sulphides, by means of which volatile substances, particularly iodine and diiodised aromatic compounds, can be separated from the polymers.
    Type: Application
    Filed: April 29, 2013
    Publication date: May 7, 2015
    Inventors: Clifford Schaferskupper, Thomas Hille, Theodor Jurgens, Andre Schumann, Lars Gierszewski
  • Publication number: 20150087779
    Abstract: Methods of forming a polyarylene sulfide and systems as may be utilized in carrying out the methods are described. Included in the formation method is a filtration process for treatment of a mixture, the mixture including a polyarylene sulfide, a salt byproduct of the polyarylene sulfide formation reaction, and a solvent. The filtration process includes maintaining the downstream side of the filter medium at an increased pressure. The downstream pressure can such that the boiling temperature of the mixture at the downstream pressure can be higher than the temperature at which the polyarylene sulfide is insoluble in the solvent.
    Type: Application
    Filed: September 9, 2014
    Publication date: March 26, 2015
    Inventors: Hendrich Chiong, Michael Haubs, Damian Feord, Mark Shatzer, Jacob Grayson
  • Publication number: 20150087805
    Abstract: Methods, devices, and systems that can be utilized in separating a polymer from other compounds of a polymer formation process are described. The methods utilize multiple sedimentors in a countercurrent flow design in conjunction with different solvent solutions in the multiple sedimentors to separate a product polymer from other compounds of a polymer formation process. The sedimentors include feed inlets that can encourage contact between countercurrent flows and improve mass transfer rates between the countercurrent flows.
    Type: Application
    Filed: September 9, 2014
    Publication date: March 26, 2015
    Inventors: Venkata Nekkanti, Michael Haubs
  • Publication number: 20150087780
    Abstract: A method for formation of a semi-crystalline polyarylene sulfide is described. The method can include reaction of sulfur-containing monomer with a dihaloaromatic monomer in an organic amide solvent to form a polymer following by combination of the polymer with a crystallization solution. The crystallization solution is pre-heated and the mixture formed is slowly cooled to crystallize the polymer.
    Type: Application
    Filed: September 9, 2014
    Publication date: March 26, 2015
    Inventors: Hendrich Chiong, Michael Haubs, Damian Feord, Stanley Leonard, Jacob Grayson, Venkata Nekkanti
  • Patent number: 8981041
    Abstract: A production process of a poly(arylene sulfide) (PAS), including a polymerization step of forming a PAS from a sulfur source that is an alkali metal (hydro)sulfides and a dihalo-aromatic compound in an organic amide solvent; a separation step of PAS particles; a countercurrent washing step that is a step of washing the PAS particles with water and/or an organic solvent, wherein a downward current of a PAS particle-containing aqueous slurry is continuously brought into countercurrent contact with an upward current of a washing liquid; a PAS particle re-separation step of capturing a washing waste liquid by a PAS particle re-separating unit, in which a micro-slit filter has been installed, and then re-separating the PAS particles from the micro-slit filter, preferably using a backwashing unit, to discharge them; and a collecting step of the PAS particles discharged, and a production apparatus of a poly(arylene sulfide).
    Type: Grant
    Filed: July 6, 2011
    Date of Patent: March 17, 2015
    Assignee: Kureha Corporation
    Inventors: Takayuki Kimura, Tomoyoshi Koizumi, Mitsuhiro Matsuzaki
  • Publication number: 20150057429
    Abstract: A production method includes a process (I) of heating a cyclic polyarylene sulfide composition under reduced pressure and a process (II) of heating and polymerizing a cyclic polyarylene sulfide composition. This simple method allows for production of a polyarylene sulfide of the higher molecular weight and can produce a polyarylene sulfide having a narrow molecular weight distribution, low gas generation and high industrial usability. Additionally, pelletization after the process (I) can produce a cyclic polyarylene sulfide pellet having ease of conveyance, excellent molding processability, less gas generation amount and high industrial usability.
    Type: Application
    Filed: February 27, 2013
    Publication date: February 26, 2015
    Inventors: Akinori Kanomata, Yosuke Nishimura, Shunsuke Horiuchi, Shu Kaiho, Kazusada Takeda, Koji Yamauchi, Junya Suzuki
  • Patent number: 8957182
    Abstract: The present invention relates to a polyarylene sulfide that is prepared from a composition including 100 parts by weight of solid sulfur, 500 to 10,000 parts by weight of iodinated aryl compounds, and 0.03 to 30 parts by weight of a sulfur-containing polymerization terminator with respect to 100 parts by weight of the solid sulfur, and has a melting temperature (Tm) of 255 to 285° C., and luminosity of 40 or higher as defined by the CIE Lab color model, and a process of preparing the same. The PAS resin is prepared from a composition including a sulfur-containing polymerization terminator and thus has excellent thermal properties and luminosity.
    Type: Grant
    Filed: February 13, 2014
    Date of Patent: February 17, 2015
    Assignee: SK Chemicals Co., Ltd.
    Inventors: Young-Rok Lee, Il-Hoon Cha, Yong-Jun Shin, Jun-Sang Cho
  • Publication number: 20150013296
    Abstract: The present invention provides: a polyphenylene sulfide fiber that has excellent tensile strength; and a polyphenylene sulfide fiber that decreases in toughness to a small extent even when subjected to a long-term heat treatment and has excellent tensile strength. The polyphenylene sulfide fiber according to the present invention is characterized by comprising a polyphenylene sulfide resin having a weight average molecular weight of 50000 to 80000 inclusive, having a rigid amorphous content of 50% or more, and having a crystal size of 5 nm or more in the direction of a (111) crystal plane.
    Type: Application
    Filed: February 19, 2013
    Publication date: January 15, 2015
    Inventors: Takeshi Sugimoto, Keiji Kaiho, Koichiro Maeda
  • Patent number: 8883959
    Abstract: A method for producing a polyarylene sulfide resin, comprising: producing a slurry (I) containing a solid alkali metal sulfide by allowing a hydrous alkali metal sulfide, or a hydrous alkali metal hydrosulfide and an alkali metal hydroxide, and an aliphatic cyclic compound (c1) that can be ring-opened by hydrolysis to react with each other while conducting dehydration in the presence of a non-hydrolyzable organic solvent; adding an aprotic polar organic solvent after the production of the slurry (I) and distilling off water to conduct dehydration; and conducting polymerization by allowing a polyhaloaromatic compound (a), an alkali metal hydrosulfide (b), and an alkali metal salt (c2) of a hydrolysate of the compound (c1) to react with each other in the slurry (I) in a state where the amount of water existing in the reaction system is 0.02 moles or less relative to 1 mole of the aprotic polar organic solvent.
    Type: Grant
    Filed: January 9, 2014
    Date of Patent: November 11, 2014
    Assignee: DIC Corporation
    Inventor: Toshio Hinokimori
  • Patent number: 8883960
    Abstract: The present invention relates to a polyarylene sulfide that is prepared from a composition including 100 parts by weight of solid sulfur, 500 to 10,000 parts by weight of iodinated aryl compounds, and 0.03 to 30 parts by weight of a sulfur-containing polymerization terminator with respect to 100 parts by weight of the solid sulfur, and has a melting temperature (Tm) of 255 to 285° C., and luminosity of 40 or higher as defined by the CIE Lab color model, and a process of preparing the same. The PAS resin is prepared from a composition including a sulfur-containing polymerization terminator and thus has excellent thermal properties and luminosity.
    Type: Grant
    Filed: January 4, 2008
    Date of Patent: November 11, 2014
    Assignee: SK Chemicals Co., Ltd.
    Inventors: Young-Rok Lee, Il-Hoon Cha, Yong-Jun Shin, Jun-Sang Cho
  • Publication number: 20140256907
    Abstract: There is provided a production method of a cyclic polyarylene sulfide from a reaction mixture including at least a sulfidizing agent (a), a dihalogenated aromatic compound (b) and an organic polar solvent (c). The production method includes: a process 1 of heating the reaction mixture having an arylene unit of not less than 0.80 mol but less than 1.05 mol per 1 mol of the sulfur content in the reaction mixture; and subsequent to the process 1, a process 2 of further causing the reaction to proceed after addition of the dihalogenated aromatic compound (b) to have the arylene unit of not less than 1.05 mol and not greater than 1.50 mol per 1 mol of the sulfur content in the reaction mixture.
    Type: Application
    Filed: October 22, 2012
    Publication date: September 11, 2014
    Applicant: TORAY INDUSTRIES, INC.
    Inventors: Tomoyuki Odashima, Shunsuke Horiuchi, Naoto Kumagai, Koji Yamauchi
  • Patent number: 8759478
    Abstract: A method for preparing polyarylene sulfide having reduced iodine content and excellent thermal stability is described. The method includes reacting a composition comprising diiodide aromatic compounds, sulfur compounds, and a polymerization terminator. The preparation method may effectively reduce iodine content of polyarylene sulfide to prevent corrosion of post processing equipment, improve properties of polyarylene sulfide such as thermal stability, and the like, and thus, it may be usefully applied in the industrial field relating to preparation of polyarylene sulfide.
    Type: Grant
    Filed: January 31, 2011
    Date of Patent: June 24, 2014
    Assignee: SK Chemicals Co., Ltd.
    Inventors: Yong-Jun Shin, Il-Hoon Cha, Jae-Bong Lim, Sung-Gi Kim
  • Patent number: 8742061
    Abstract: It is aimed to provide a polyarylene sulfide film for an acoustic instrument vibrating plate excellent in heat resistance, molding processability, acoustic properties, and also heat moldability. Provided is a polyarylene sulfide film wherein the elongation at break in either a longitudinal direction or a width direction of the film is 100% or more and 250% or less, and the Young's modulus in either a longitudinal direction or a width direction of the film is 1.5 GPa or more and less than 4 GPa.
    Type: Grant
    Filed: December 19, 2012
    Date of Patent: June 3, 2014
    Assignee: Toray Industries, Inc.
    Inventors: Tetsuya Machida, Yasuyuki Imanishi, Masatoshi Ohkura, Takuji Higashioji
  • Publication number: 20140128568
    Abstract: A method for producing a polyarylene sulfide resin, comprising: producing a slurry (I) containing a solid alkali metal sulfide by allowing a hydrous alkali metal sulfide, or a hydrous alkali metal hydrosulfide and an alkali metal hydroxide, and an aliphatic cyclic compound (c1) that can be ring-opened by hydrolysis to react with each other while conducting dehydration in the presence of a non-hydrolyzable organic solvent; adding an aprotic polar organic solvent after the production of the slurry (I) and distilling off water to conduct dehydration; and conducting polymerization by allowing a polyhaloaromatic compound (a), an alkali metal hydrosulfide (b), and an alkali metal salt (c2) of a hydrolysate of the compound (c1) to react with each other in the slurry (I) in a state where the amount of water existing in the reaction system is 0.02 moles or less relative to 1 mole of the aprotic polar organic solvent.
    Type: Application
    Filed: January 9, 2014
    Publication date: May 8, 2014
    Applicant: DIC Corporation
    Inventor: Toshio Hinokimori
  • Patent number: 8680230
    Abstract: The invention provides a production process of a poly(arylene sulfide) which contains a step of polymerizing a sulfur source and a dihalo-aromatic compound in an organic amide solvent, said polymerization step containing a phase-separation polymerization step that the polymerization reaction is continued in the presence of a phase separation agent in a phase-separated state, wherein a monohalo-organic compound is added in a proportion of 0.005 to 20 mol per 100 mol of the charged sulfur source into the polymerization reaction system at the time a conversion of the dihalo-aromatic compound has reached 80 to 99% after initiation of the polymerization reaction and before the liquid phase becomes the phase-separated state to be reacted with a formed polymer, and the liquid phase within the polymerization reaction system is then converted to the phase-separated state to continue the polymerization reaction.
    Type: Grant
    Filed: June 10, 2009
    Date of Patent: March 25, 2014
    Assignee: Kureha Corporation
    Inventors: Akihiro Konno, Ken-ichi Takaki, Hiroshi Sakabe
  • Patent number: 8609790
    Abstract: The invention provides a production process of a granular poly(arylene sulfide) by polymerizing a sulfur source and a dihalo-aromatic compound in an organic amide solvent by a polymerization process containing a phase-separation polymerization step, wherein the production process contains a step I of adding an aromatic compound in a proportion of 0.01 to 20 mol per 100 mol of the organic amide solvent into the liquid phase containing the organic amide solvent and a formed polymer within the polymerization reaction system, said liquid phase being in the phase-separated state, after the phase-separation polymerization step; a step II of cooling the liquid phase within the polymerization reaction system; and a step III of collecting the formed polymer from the liquid phase.
    Type: Grant
    Filed: June 10, 2009
    Date of Patent: December 17, 2013
    Assignee: Kureha Corporation
    Inventors: Kenji Suzuki, Tomoyoshi Koizumi, Yoshinori Shiojiri
  • Patent number: 8603599
    Abstract: There are provided, according to the present invention, a resin composition for hollow blow-molded article which is obtained in a high productivity on an industrial scale with excellent moldability and drawdown resistance, and the production method thereof, by melting and mixing a polyarylene sulfide resin including a terminal carboxyl group within the resin in an amount of 25 to 45 (?mol/g), and having a non-Newtonian index of 0.90 to 1.15 and also a melt viscosity as measured at 300° C. within the range of 1,000 poise to 3,000 poise and an epoxy group-containing polyolefin so that the proportion of the epoxy group-containing polyolefin is 5 to 30 parts by mass with respect to 100 parts by mass of the polyarylene sulfide resin; and a hollow blow-molded article with excellent mechanical strength, such as the heat resistance and impact resistance, and surface appearance, and the production method thereof.
    Type: Grant
    Filed: May 24, 2011
    Date of Patent: December 10, 2013
    Assignee: DIC Corporation
    Inventors: Shingo Matsuo, Toshio Hinokimori
  • Patent number: 8586694
    Abstract: The polymerization catalyst for a polythiourethane-based optical material of the present invention includes a sulfonate represented by the following general formula (1). Furthermore, in the formula, R1, R2, R3 and R4 each independently represent an alkyl group having 1 to 18 carbon atoms, R1, R2, R3 and R4 may be bonded to each other to form a ring. R5 represents a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, and X represents a nitrogen atom or a phosphorus atom.
    Type: Grant
    Filed: February 4, 2008
    Date of Patent: November 19, 2013
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Masanori Iwazumi, Nobuo Kawato, Mamoru Tanaka, Hidetoshi Hayashi, Seiichi Kobayashi
  • Patent number: 8575293
    Abstract: According to the present invention, a resin compound for optical material, comprising (a) an episulfide compound represented by a specific structural formula, (b) a xylylenedithiol compound and (c) a xylylenediisocyanate compound can be provided. In a preferable embodiment of the present invention, a resin compound for optical material having superb optical properties, a high density and a high thermal resistance can be provided. Also according to the present invention, an optical material obtained by curing the above-described resin compound can be provided.
    Type: Grant
    Filed: September 11, 2007
    Date of Patent: November 5, 2013
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hiroshi Horikoshi, Motoharu Takeuchi
  • Patent number: 8546518
    Abstract: A method is provided for producing a polyarylene sulfide by reacting a sulfidizing agent with a dihalogenated aromatic compound in an organic polar solvent in the presence of an alkali metal hydroxide, the method includes <Step 1>: carrying out the reaction in such a manner that the polymerization time in a temperature range of 230° C. to less than 245° C. (T1a) is not less than 30 minutes and less than 3.5 hours and that the conversion ratio of the dihalogenated aromatic compound at the end of the step is 70 to 98 mol. % and <Step 2>: carrying out the reaction in such a manner that the polymerization time in a temperature range of 245° C. to less than 280° C. (T2) is not less than 5 minutes and less than 1 hour.
    Type: Grant
    Filed: August 26, 2010
    Date of Patent: October 1, 2013
    Assignee: Toray Industries, Inc.
    Inventors: Takeshi Unohara, Hiroyuki Isago, Toru Nishimura, Masahiro Inohara
  • Patent number: 8492502
    Abstract: The present invention relates to a process of producing polyarylene sulfide (PAS) and PAS resin produced therefrom, and more specifically, to a process of preparing polyarylene sulfide with better thermal properties and luminosity than conventional PAS and the PAS resin produced therefrom, including the steps of: a) melting and mixing a composition including solid sulfur, iodinated aryl compounds, and a polymerization terminator; b) polymerizing the molten mixture of step a) for 1 to 30 hours while increasing the temperature and decreasing the pressure from initial reaction conditions of a temperature of 180 to 250° C. and a pressure of 50 to 450 Torr to final reaction conditions of a temperature of 270 to 350° C. and a pressure of 0.001 to 20 Torr; and c) heating the reaction product of step b) at a temperature of 270 to 350° C. for 1 to 25 hours.
    Type: Grant
    Filed: January 4, 2008
    Date of Patent: July 23, 2013
    Assignee: SK Chemicals Co., Ltd.
    Inventors: Young-Rok Lee, II-Hoon Cha, Jun-Sang Cho
  • Patent number: 8445629
    Abstract: A method for producing an acid group-containing polyarylene sulfide of the present invention includes a reaction step of reacting a polyhaloaromatic compound (a), an alkali metal hydrosulfide (b), and an alkali metal carboxylate (c) in the presence of a solid alkali metal sulfide and a lithium ion.
    Type: Grant
    Filed: August 7, 2007
    Date of Patent: May 21, 2013
    Assignee: DIC Corporation
    Inventors: Toshio Hinokimori, Nobuhiko Yamauchi, Takashi Furusawa
  • Publication number: 20130116401
    Abstract: A production process of a poly(arylene sulfide) (PAS), including a polymerization step of forming a PAS from a sulfur source that is an alkali metal (hydro)sulfides and a dihalo-aromatic compound in an organic amide solvent; a separation step of PAS particles; a countercurrent washing step that is a step of washing the PAS particles with water and/or an organic solvent, wherein a downward current of a PAS particle-containing aqueous slurry is continuously brought into countercurrent contact with an upward current of a washing liquid; a PAS particle re-separation step of capturing a washing waste liquid by a PAS particle re-separating unit, in which a micro-slit filter has been installed, and then re-separating the PAS particles from the micro-slit filter, preferably using a backwashing unit, to discharge them; and a collecting step of the PAS particles discharged, and a production apparatus of a poly(arylene sulfide).
    Type: Application
    Filed: July 6, 2011
    Publication date: May 9, 2013
    Inventors: Takayuki Kimura, Tomoyoshi Koizumi, Mitsuhiro Matsuzaki
  • Patent number: 8426552
    Abstract: A method for producing an acid group-containing polyarylene sulfide of the present invention includes a reaction step of reacting a polyhaloaromatic compound (a), an alkali metal hydrosulfide (b), an alkali metal carboxylate (c), and an aromatic compound (d) having an elimination group and an acid group, which function in a nucleophilic reaction, in the presence of a solid alkali metal sulfide.
    Type: Grant
    Filed: August 7, 2007
    Date of Patent: April 23, 2013
    Assignee: DIC Corporation
    Inventors: Toshio Hinokimori, Nobuhiko Yamauchi, Takashi Furusawa
  • Publication number: 20130065054
    Abstract: Disclosed is a process for producing poly(arylene sulfide) which includes: a polymerization step of polymerizing a dihalogenated aromatic compound and at least one sulfur source selected from the group consisting of alkali metal sulfides and alkali metal hydrogen sulfides in an organic amide solvent, preferably in the presence of a phase separating agent; a separation step of separating a polymer from a reaction liquid containing a produced polymer after the polymerization step; a washing step of washing the polymer with a washing liquid that consists of water and/or an organic solvent; and a separated liquid treatment step of bringing both a separated liquid that has been recovered after the separation of the polymer in the separation step and a separated liquid containing a wash waste liquid that has been recovered after the separation of the polymer in the washing step into contact with an alkaline compound. Also disclosed is poly(arylene sulfide).
    Type: Application
    Filed: April 21, 2011
    Publication date: March 14, 2013
    Applicant: KUREHA CORPORATION
    Inventors: Yoshihiro Ichinose, Masanori Kobayashi, Tomoyoshi Koizumi, Mitsuhiro Matsuzaki
  • Publication number: 20130012635
    Abstract: A thermoplastic material comprises the cure product of a thermoplastic polymer having a thermal decomposition temperature greater than or equal to about 200° C., the thermoplastic polymer being cured at a temperature of about 200° C. to about 400° C., for a total time of less than or equal to 200 hours. An article is formed from the thermoplastic material.
    Type: Application
    Filed: July 8, 2011
    Publication date: January 10, 2013
    Applicant: BAKER HUGHES INCORPORATED
    Inventors: Jiaxiang Ren, David Peter Gerrard, James Edward Goodson, Lillian Guo, Ping Duan
  • Patent number: 8349974
    Abstract: A biaxially oriented polyarylene sulfide film which has an excellent elongation at break and flatness is provided. The biaxially oriented film may be a biaxially oriented polyarylene sulfide film which is substantially composed of a polyarylene sulfide resin (A), wherein one of the elongations at break in the machine direction and in the transverse direction of the film is not lower than 110%; one of the breaking stresses in the machine direction and in the transverse direction of the film of the film is not higher than 200 MPa; and both of the heat shrinkage ratio in the machine direction of the film and that in the transverse direction of the film at 260° C. for 10 minutes are not less than 0% and not more than 10%.
    Type: Grant
    Filed: May 7, 2008
    Date of Patent: January 8, 2013
    Assignee: Toray Industries, Inc.
    Inventors: Tetsuya Machida, Masatoshi Ohkura, Yasuyuki Imanishi
  • Patent number: 8344094
    Abstract: An optical material is provided that has a high transmittance, a high refractive index, a low Abbe constant, a high secondary dispersion property, and a low water absorption rate. The optical material includes a polymer of a mixture which contains: a sulfur-containing compound represented by the following general formula (1): a sulfur-containing compound represented by the following general formula (2): and an energy polymerization initiator, in which a content of the sulfur-containing compound represented by the chemical formula (2) is 10% by weight or more to 60% by weight or less, an Abbe constant (?d) of the polymer of the mixture satisfies 18<?d<23, and a secondary dispersion property (?g,F) thereof satisfies 0.68<?g,F<0.69.
    Type: Grant
    Filed: September 8, 2009
    Date of Patent: January 1, 2013
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hidefumi Iwasa, Shigeo Kiso, Terunobu Saitoh, Toshiji Nishiguchi
  • Publication number: 20120322972
    Abstract: A column-type solid-liquid countercurrent contact apparatus, a washing apparatus for solid particles such as poly(arylene sulfide) (PAS) particles, a PAS manufacturing apparatus, a method of solid-liquid countercurrent contact, a method of washing solid particles such as PAS particles, and a method of manufacturing PAS, wherein a column top part, a column body part, and a column bottom part are included, the column body part is provided with a plurality of stirring chambers connected in the vertical direction and mutually divided by a ring-shaped partitioning plate, a paddle blade (a blade diameter/a diameter of the stirring chamber?0.65 and the blade diameter/the diameter of the stirring chamber?0.10) and a baffle are disposed at each of the plurality of stirring chambers, and a disc having a size covering at least a part of a communication opening positioned below the paddle blade is attached to a rotating shaft or to the paddle blade.
    Type: Application
    Filed: February 23, 2011
    Publication date: December 20, 2012
    Inventors: Tomoyoshi Koizumi, Kimihiko Kikuchi
  • Patent number: 8329832
    Abstract: A method for producing a cyclic polyarylene sulfide, wherein a cyclic polyarylene sulfide is produced by heating a reaction mixture which is composed of at least a linear polyarylene sulfide (a), a sulfidizing agent (b), a dihalogenated aromatic compound (c) and an organic polar solvent (d). This method for producing a cyclic polyarylene sulfide is characterized in that not less than 1.25 liters of the organic polar solvent is used per 1 mole of the sulfur content in the reaction mixture. This method enables to efficiently produce a cyclic polyarylene sulfide, more specifically cyclic oligoarylene sulfide by an economical and simple process in short time.
    Type: Grant
    Filed: February 27, 2008
    Date of Patent: December 11, 2012
    Assignee: Toray Industries, Inc.
    Inventors: Shunsuke Horiuchi, Kohei Yamashita, Kayo Tsuchiya, Koji Yamauchi
  • Patent number: 8263734
    Abstract: The techniques provide a system and a method of producing polyphenylene sulfide (PPS) polymer. The PPS polymer is produced by reacting a sulfur source and a dihaloaromatic compound in the presence of a polar organic compound in a polymerization mixture in a polymerization vessel. The PPS polymer is washed with a base to lower the oligomer content of the PPS polymer and thus the off-gassing during processing.
    Type: Grant
    Filed: February 13, 2009
    Date of Patent: September 11, 2012
    Assignee: Chevron Phillips Chemical Company LP
    Inventors: Jeffrey S. Fodor, Aubrey South, Jr.
  • Patent number: 8242233
    Abstract: This invention relates to a method of preparing poly(arylene sulfide) (PAS) from an iodo compound and a sulfur compound, and more particularly, to a method of preparing PAS, including adding a sulfur-containing polymerization terminator when PAS is produced using an iodo compound as an intermediate. Thereby, in final PAS, the residual iodine content may be maintained at the same level or decreased and other properties may be maintained at equal or superior levels, thanks to the use of the sulfur-containing polymerization terminator, which is much lower in price than conventional polymerization terminators.
    Type: Grant
    Filed: August 21, 2007
    Date of Patent: August 14, 2012
    Assignee: SK Chemicals Co., Ltd.
    Inventors: Young Rok Lee, Il Hoon Cha, Jun Sang Cho
  • Patent number: 8183336
    Abstract: In a process for producing a poly(arylene sulfide) by polymerizing a sulfur source and a dihalo-aromatic compound in the presence of an alkali metal hydroxide in an organic amide solvent, the production process comprises washing a polymer obtained by the polymerization with a hydrophilic organic solvent containing water in a proportion of 1 to 30% by weight, thereby collecting a purified polymer, the content of nitrogen contained in an extract extracted by a mixed solvent containing 40% by weight of acetonitrile and 60% by weight of water from the purified polymer is at most 50 ppm on the basis of the weight of the polymer, and a poly(arylene sulfide), the content of nitrogen contained in an extract extracted by a mixed solvent containing 40% by weight of acetonitrile and 60% by weight of water from the purified polymer is at most 50 ppm on the basis of the weight of the polymer.
    Type: Grant
    Filed: May 28, 2010
    Date of Patent: May 22, 2012
    Assignee: Kureha Corporation
    Inventors: Hiroyuki Sato, Koichi Suzuki, Hirohito Kawama
  • Patent number: 8138279
    Abstract: A biaxially oriented polyarylene sulfide film made of a polyarylene sulfide resin composition has a melt crystallization temperature of not lower than 160° C. and not higher than 220° C. The biaxially oriented polyarylene sulfide film contains 70 to 99 parts by weight of the polyarylene sulfide and 1 to 30 parts by weight of thermoplastic resin A; the thermoplastic resin A constitutes a dispersed phase having an average dispersion diameter of 50 nm to 500 nm. The biaxially oriented polyarylene sulfide film has a breaking stress at 200° C. in the machine direction and/or transverse direction of not less than 30 MPa and not more than 90 MPa and has an elongation at break at 200° C. in the machine direction and/or transverse direction of not less than 100% and not more than 250%.
    Type: Grant
    Filed: May 9, 2007
    Date of Patent: March 20, 2012
    Assignee: Toray Industries, Inc.
    Inventors: Tetsuya Machida, Masatoshi Ohkura, Yasuyuki Imanishi, Takuji Higashioji
  • Patent number: 8076447
    Abstract: A poly(arylene sulfide) having properties that a melt viscosity is 1 to 3,000 Pa·s as measured under conditions of a temperature of 310° C. and a shear rate of 1,216 sec?1, a pH is 7.0 to 12.0 as measured in a mixed solvent of water/acetone (volume ratio=2/1), a crystallization temperature is at most 220° C. as measured in the course of lowing the temperature of the polymer at a rate of 10° C./min from a molten state, and a whiteness degree is at least 70 as measured in the form of a melt molded or formed product, and a production process thereof.
    Type: Grant
    Filed: December 16, 2009
    Date of Patent: December 13, 2011
    Assignee: Kureha Corporation
    Inventors: Hiroyuki Sato, Koichi Suzuki, Hirohito Kawama
  • Publication number: 20110178268
    Abstract: The invention provides a production process of a granular poly(arylene sulfide) by polymerizing a sulfur source and a dihalo-aromatic compound in an organic amide solvent by a polymerization process containing a phase-separation polymerization step, wherein the production process contains a step I of adding an aromatic compound in a proportion of 0.01 to 20 mol per 100 mol of the organic amide solvent into the liquid phase containing the organic amide solvent and a formed polymer within the polymerization reaction system, said liquid phase being in the phase-separated state, after the phase-separation polymerization step; a step II of cooling the liquid phase within the polymerization reaction system; and a step III of collecting the formed polymer from the liquid phase.
    Type: Application
    Filed: June 10, 2009
    Publication date: July 21, 2011
    Inventors: Kenji Suzuki, Tomoyoshi Koizumi, Yoshinori Shiojiri
  • Publication number: 20110114274
    Abstract: A polyphenylene sulfide fiber has an amount of heat of crystallization measured by DSC is 10 J/g or more and the degree of shrinkage on dry heating of 150° C.×30 minutes is 20% or less. A method produces a densified wet-laid nonwoven fabric, wherein a wet-laid nonwoven fabric that contains 60 to 100% by mass of a polyphenylene sulfide fiber having an amount of heat of crystallization of 10 J/g or more and wherein the amount of heat of crystallization of the polyphenylene sulfide fiber before heating-pressurizing treatments is 5 J/g or more is subjected to heating-pressurizing treatment at a temperature that is not lower than the glass transition temperature and not higher than the melting point of the polyphenylene sulfide fiber.
    Type: Application
    Filed: July 8, 2009
    Publication date: May 19, 2011
    Applicant: TORAY INDUSTRIES, INC.
    Inventors: Tomoko Takano, Koji Sugano, Yuhei Maeda, Takeshi Sugimoto
  • Publication number: 20110077351
    Abstract: Disclosed are thioethers, methods for preparing such thioethers, and curable compositions, such as coating and sealant compositions, that include such thioethers. The thioethers can be the reaction product of (a) an alpha, omega dihalo organic compound, (b) a metal hydrosulfide, and (c) a metal hydroxide.
    Type: Application
    Filed: December 13, 2010
    Publication date: March 31, 2011
    Applicant: PRC-DeSoto International, Inc.
    Inventors: John R. Gilmore, Chandra B. Rao
  • Patent number: 7867612
    Abstract: A composite material is described that contains a reinforcing resin and reinforcing fibers, wherein the reinforcing fibers have a coating containing polyphenylene sulfide and the proportion of polyphenylene sulfide relative to the uncoated fibers is 0.001 to <0.01 wt. %. The composite material shows higher apparent interlaminar shear strength and bending strength as compared with similar composite materials having no PPS coating in the above concentration range.
    Type: Grant
    Filed: March 28, 2003
    Date of Patent: January 11, 2011
    Assignee: Toho Tenax Europe GmbH
    Inventors: Klaus Peter Schwung, Bernd Wohlmann