Solid Polymer Derived From Alkali Metal Sulfide And Halogenated Aromatic Reactant, E.g., Polyarylene Sulfide, Etc. Patents (Class 525/537)
  • Patent number: 11795272
    Abstract: A method for producing PAS having an average particle size of 50 ?m or greater and 550 ?m or less is provided. The method can include: (1) a preparation step of preparing a prepared mixture containing an organic polar solvent, a sulfur source, and a dihalo aromatic compound; (2) a pre-stage polymerization step of initiating a polymerization reaction by heating the prepared mixture to produce a prepolymer; (3) a phase separation step of adding water as a phase separation agent to a reaction mixture in a reaction system to form a phase separation state; and (4) a post-stage polymerization step of continuing the polymerization reaction after the phase separation step, in which an organic sulfonic acid metal salt having a specific solubility in water is contained in the prepared mixture or the reaction mixture.
    Type: Grant
    Filed: November 25, 2020
    Date of Patent: October 24, 2023
    Assignee: Kureha Corporation
    Inventors: Takeshi Sato, Yoshinori Suzuki
  • Patent number: 11292155
    Abstract: A polyphenylene sulfide resin composition includes (A) 100 parts by weight of an acid-treated polyphenylene sulfide resin, (B) 10 to 100 parts by weight of a glass fiber, and (C) 0.1 to 10 parts by weight of an amino group-containing alkoxysilane compound, wherein the polyphenylene sulfide resin composition has an exothermic peak temperature (Tmc) of 195° C. to 225° C., the exothermic peak temperature being observed during a crystallization caused when the polyphenylene sulfide resin composition is melted by heating to 340° C. and then cooled at a rate of 20° C./minute, using a differential scanning calorimeter.
    Type: Grant
    Filed: March 16, 2018
    Date of Patent: April 5, 2022
    Assignee: Toray Industries, Inc.
    Inventors: Hisashi Yamanoue, Gen Noguchi, Kei Saito
  • Patent number: 11174388
    Abstract: A polyphenylene sulfide resin composition exhibits excellent initial toughness and toughness after a long-term high temperature treatment typified by a tensile elongation at break after a dry heat treatment without impairing mechanical strength, chemical resistance and electrical insulation properties. The polyphenylene sulfide resin composition includes 0.01 to 10 parts by weight of an organosilane compound and 0.01 to 5 parts by weight of a metal salt of phosphorus oxoacid based on 100 parts by weight of a polyphenylene sulfide resin, and a tensile elongation at break, which is measured in accordance with ASTM-D638 under the conditions of a tensile speed of 10 mm/min and an ambient temperature of 23° C. after treating at 200° C. for 500 hours using an ASTM No. 4 dumbbell test piece obtained by injection molding the composition, is 10% or more.
    Type: Grant
    Filed: February 15, 2018
    Date of Patent: November 16, 2021
    Assignee: Toray Industries, Inc.
    Inventors: Tomoya Yoshida, Hiroyuki Isago, Takeshi Unohara, Hideki Matsumoto
  • Patent number: 10882959
    Abstract: A method for forming a polyarylene sulfide is described. The method can include a multi-step cooling and precipitation process in which the cooling rate of the solution that carries the polymer is decreased during a portion of the overall cooling. This slower cooling period can encompass at least a portion of the period during which the polymer precipitates from the solution. The precipitation process can form polyarylene sulfide particles with good particle integrity and a narrow particle size distribution, which can reduce fines and improve downstream processing and final product characteristics.
    Type: Grant
    Filed: October 22, 2018
    Date of Patent: January 5, 2021
    Assignee: Ticona LLC
    Inventor: Hendrich A. Chiong
  • Patent number: 10351686
    Abstract: A method of forming a modified thermoplastic structure for a down-hole application comprises forming a thermoplastic structure comprising at least one thermoplastic material formulated for crosslinking using an electron beam process. The thermoplastic structure is exposed to at least one electron beam to crosslink polymer chains of the thermoplastic structure. Other methods of forming a modified thermoplastic structure, and a down-hole tool are also described.
    Type: Grant
    Filed: March 13, 2013
    Date of Patent: July 16, 2019
    Assignee: Baker Hughes, a GE company, LLC
    Inventors: Michal Benes, Jiaxiang Ren
  • Patent number: 10287396
    Abstract: A polymer is provided. The polymer has a repeating unit having a structure represented by Formula (I) or Formula (II) wherein Ar1 and Ar2 can be substituted or unsubstituted aryl diradical; Y? can be R2SO3? or ClO4?; R1 can be C1-6 alkyl; Ar1 and Ar2 are different; and, R2 can be C1-6 alkyl, substituted or unsubstituted aromatic ring, or C1-6 haloalkyl.
    Type: Grant
    Filed: December 29, 2016
    Date of Patent: May 14, 2019
    Assignee: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE
    Inventors: Po-Hsien Ho, Chih-Hsiang Lin, Meng-Hsin Chen, Cheng-Hsing Fan, Hsin-Ching Kao, Yih-Her Chang
  • Patent number: 10221314
    Abstract: Described herein is a composition comprising a polymer blend. The polymer blend comprises 92 to 99 weight percent of a polyphenylene ether sulfone and 1 to 8 weight percent of a polyalkylene terephthalate, wherein weight percent is based on the combined weight of the polyphenylene ether sulfone and polyalkylene terephthalate. The polymer blend has a transmittance greater than or equal to 60% and a haze less than or equal to 10% at a thickness of 3.2 millimeters, as determined according to ASTM D1003.
    Type: Grant
    Filed: March 8, 2016
    Date of Patent: March 5, 2019
    Assignee: SABIC GLOBAL TECHNOLOGIES B.V.
    Inventors: Robert Russell Gallucci, Mark A. Sanner
  • Patent number: 10081710
    Abstract: A branched polyarylene sulfide resin includes an —S— substituent group with a cleaved disulfide compound, which has a halogen content of 4,000 ppm or less, a melt viscosity as measured at a temperature of 330° C. and a shear rate of 2 sec?1 of 1.0×104 to 50.0×104 Pa·s, and a melt viscoelasticity tan ? as measured at a temperature of 310° C. and an angular velocity of 1 rad/sec of 0.1 to 0.6.
    Type: Grant
    Filed: October 18, 2017
    Date of Patent: September 25, 2018
    Assignee: KUREHA CORPORATION
    Inventors: Akihiro Konno, Yasuhiro Suzuki
  • Patent number: 10072123
    Abstract: A method of producing polyarylene sulfide (PAS) by subjecting a sulfur source and a dihalo aromatic compound (DHA) to polymerization reaction in an organic amide solvent under alkaline conditions, the method suppressing side reactions or the like and yielding PAS having a high degree of polymerization at a high yield is provided; and PAS having a high degree of polymerization are provided. A method of producing PAS, including: a preparation step of preparing a preparation mixture containing an organic amide solvent, a sulfur source, an alkali metal hydroxide, water, and DHA, and having a pH of 12.5 or higher; a first-stage polymerization step of heating the preparation mixture to 170° C. or higher to initiate a polymerization reaction and continuing the polymerization reaction at 240 to 280° C., thereby forming a prepolymer having a DHA conversion rate of 50% or greater (at this time, a temperature increasing rate from 220° C. to 240° C. is lower than a temperature increasing rate for 240° C.
    Type: Grant
    Filed: December 18, 2015
    Date of Patent: September 11, 2018
    Assignee: KUREHA CORPORATION
    Inventors: Akihiro Konno, Ken-Ichi Takaki, Hiroyuki Sato
  • Patent number: 10040910
    Abstract: A heat-resistant, chemical-resistant polyphenylene sulfide block copolymer containing polyphenylene sulfide units and aromatic polyester units, wherein the polyphenylene sulfide units have a number average molecular weight in the range of 6,000 to 100,000. Provided is a polyphenylene sulfide block copolymer that overcomes the disadvantages of block copolymers including a low-molecular-weight polyphenylene sulfide segment and having poor heat resistance and chemical resistance.
    Type: Grant
    Filed: December 24, 2014
    Date of Patent: August 7, 2018
    Assignee: TORAY INDUSTRIES, INC.
    Inventors: Kohei Yamashita, Takeshi Unohara, Kosaku Takeuchi, Daisuke Yamamoto, Koji Yamauchi
  • Patent number: 9765219
    Abstract: Components for heavy duty trucks are described that exhibit high strength and flexibility. The components are formed from a polyarylene sulfide that exhibits high strength and flexibility characteristics. Methods for forming the components are also described. Formation methods include dynamic vulcanization of a polyarylene sulfide composition that includes an impact modifier dispersed throughout the polyarylene sulfide. A crosslinking agent is combined with the other components of the composition following dispersal of the impact modifier throughout the composition. The heavy duty truck components can include tubular member such as pipes and hoses that can be utilized in exhaust systems, charge air systems, urea tanks, fuel systems, and so forth.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: September 19, 2017
    Assignee: Ticona LLC
    Inventors: Rong Luo, Xinyu Zhao
  • Patent number: 9758674
    Abstract: Flowlines for use in oil and gas applications are described. The flowlines include a barrier layer that includes polyarylene sulfide composition that exhibits high strength and flexibility characteristics. Methods for forming the flowlines are also described. Formation methods include dynamic vulcanization of a polyarylene sulfide composition that includes an impact modifier dispersed throughout the polyarylene sulfide. A crosslinking agent is combined with the other components of the composition following dispersal of the impact modifier throughout the composition. The flowlines can include production fluid flowlines, supporting fluid flowlines, bundled flowlines, etc. and can be utilized as risers, pipelines, jumpers, and the like.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: September 12, 2017
    Assignee: Ticona LLC
    Inventors: Rong Luo, Xinyu Zhao
  • Patent number: 9493646
    Abstract: Components formed of blow molded thermoplastic compositions are described. The blow molded thermoplastic compositions exhibit high strength and flexibility. Methods for forming the thermoplastic compositions are also described. Formation methods include dynamic vulcanization of a composition that includes an impact modifier dispersed throughout a polyarylene sulfide. A crosslinking agent is combined with the other components of the composition following dispersal of the impact modifier. The crosslinking agent reacts with the impact modifier to form crosslinks within and among the polymer chains of the impact modifier. The compositions can exhibit excellent physical characteristics at extreme temperatures and can be used to form, e.g., tubular member such as pipes and hoses and fibers.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: November 15, 2016
    Assignee: Ticona LLC
    Inventors: Rong Luo, Xinyu Zhao, Joseph Grenci
  • Patent number: 9494262
    Abstract: A fuel line comprising a thermoplastic composition is described. The thermoplastic compositions exhibit high strength and flexibility and can be used to form one or more layers of single layer or multi-layer fuel lines. Methods for forming the thermoplastic compositions are also described. Formation methods include dynamic vulcanization of a composition that includes an impact modifier dispersed throughout a polyarylene sulfide. A crosslinking agent is combined with the other components of the composition following dispersal of the impact modifier. The crosslinking agent reacts with the impact modifier to form crosslinks within and among the polymer chains of the impact modifier. The compositions can exhibit excellent physical characteristics at extreme temperatures.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: November 15, 2016
    Assignee: Ticona LLC
    Inventors: Rong Luo, Xinyu Zhao, Joseph Grenci
  • Patent number: 9422402
    Abstract: PROBLEM: To provide a method of producing a polyarylene sulfide (PAS) such as polyphenylene sulfide (PPS) in which a dihalo aromatic compound and a sulfur source containing an alkali metal are polymerized in an organic amide solvent, whereby a PAS is produced at higher yield and the amount of NaCl produced as a by-product is reduced to not greater than half that of conventional methods, and, due to a dehydration step being omissible, PAS with excellent practical utility is produced with high productivity in a short time. SOLUTION: A method of producing a PAS in which a dihalo aromatic sulfide compound represented by the formula: X—(—Ar—S—)n—Ar—X (in the formula, Ar represents an optionally substituted aromatic group, X represents a halogen atom, and n is from 1 to 10) and a sulfur source containing an alkali metal are polymerized in an organic amide solvent; and a PAS of which an average particle size is from 10 to 5000 ?m, a melt viscosity measured at a temperature of 310° C.
    Type: Grant
    Filed: September 4, 2015
    Date of Patent: August 23, 2016
    Assignee: KUREHA CORPORATION
    Inventors: Kenji Suzuki, Yoshikatsu Satake, Yasuhiro Suzuki
  • Patent number: 9150695
    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: Grant
    Filed: October 22, 2012
    Date of Patent: October 6, 2015
    Assignee: TORAY INDUSTRIES, INC.
    Inventors: Tomoyuki Odashima, Shunsuke Horiuchi, Naoto Kumagai, Koji Yamauchi
  • Patent number: 9029484
    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: Grant
    Filed: February 27, 2013
    Date of Patent: May 12, 2015
    Assignee: Toray Industries, Inc.
    Inventors: Akinori Kanomata, Yosuke Nishimura, Shunsuke Horiuchi, Shu Kaiho, Kazusada Takeda, Koji Yamauchi, Junya Suzuki
  • Publication number: 20150126668
    Abstract: A reactive functional group-containing polyarylene sulfide resin composition having a narrow polydispersity and a low gas generation amount is manufactured by mixing a polyarylene sulfide resin (a) and a polyarylene sulfide resin (b), wherein the polyarylene sulfide (a) has a weight reduction ratio ?Wr of not higher than 0.18% under heating and an increase rate of melt viscosity of less than 1.05 times by addition of a reactive compound (c) having a reactive group relative to melt viscosity prior to addition of the reactive compound (c), and the polyarylene sulfide (b) has the weight reduction ratio ?Wr of not higher than 0.18% under heating and the increase rate of melt viscosity of not less than 1.05 times by addition of the reactive compound (c) having the reactive group relative to melt viscosity prior to addition of the reactive compound (c).
    Type: Application
    Filed: April 26, 2013
    Publication date: May 7, 2015
    Inventors: Akinori Kanomata, Shunsuke Horiuchi, Shu Kaiho, Koji Yamauchi
  • Publication number: 20150105524
    Abstract: A process comprising (a) beginning with a poly(arylene sulfide) polymer comprising a plurality of small poly(arylene sulfide) polymer particles and large poly(arylene sulfide) polymer particles, distinguishing at least a portion of the small poly(arylene sulfide) polymer particles from the large poly(arylene sulfide) polymer particles to yield distinguished small poly(arylene sulfide) polymer particles, wherein the small poly(arylene sulfide) polymer particles have a particle size of less than 2.38 mm and the large poly(arylene sulfide) polymer particles have a particle size of equal to or greater than 2.38 mm, and (b) contacting at least a portion of the distinguished small poly(arylene sulfide) polymer particles with an aqueous solution to form treated small poly(arylene sulfide) polymer particles.
    Type: Application
    Filed: October 14, 2013
    Publication date: April 16, 2015
    Applicant: Chevron Phillips Chemical Company LP
    Inventors: Thomas M. CLARK, R. Shawn CHILDRESS, Jeffrey S. FODOR, Jeffrey L. SWAN
  • Patent number: 9000104
    Abstract: A polyarylene sulfide includes 0.01 to 5 mol %, per mol of arylene sulfide structural units, of a function group selected from the group consisting of an amino group, a carboxyl group, a hydroxyl group, an acid anhydride group, an isocyanate group, an epoxy group, a silanol group, and an alkoxysilane group having a dispersity represented by (weight average molecular weight)/(number average molecular weight) of 2.5 or less and a weight loss ratio at 100° C. to 330° C. of 0.2% by weight or less when the polyarylene sulfide is subjected to thermogravimetric analysis from 50° C. to 340° C. at a temperature ramp-up rate of 20° C./min under a non-oxidative atmosphere of normal pressure.
    Type: Grant
    Filed: June 5, 2014
    Date of Patent: April 7, 2015
    Assignee: Toray Industries, Inc.
    Inventors: Akinori Kanomata, Shunsuke Horiuchi, Shu Kaiho, Koji Yamauchi
  • 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: 20150065664
    Abstract: A granular polyarylene sulfide; (i) the granular polyarylene sulfide containing an —S— substituent at the terminal, the substituent being formed by cleavage of a disulfide compound; (ii) the granular polyarylene sulfide being an oversize fraction after sifting with a sieve having a mesh size of at least 38 ?m; (iii) the granular polyarylene sulfide having a halogen content of at most 1,500 ppm; and (iv) the granular polyarylene sulfide being a granular polyarylene sulfide having a melt viscosity of 3 to 100 Pa·s when measured under conditions at a temperature of 310° C. and a shear rate of 1,200 sec?1. The granular polyarylene sulfide is well balanced in melt viscosity, halogen content, nitrogen content, thermal stability, and yield.
    Type: Application
    Filed: March 29, 2013
    Publication date: March 5, 2015
    Applicant: Kureha Corporation
    Inventors: Akihiro Konno, Ken-Ichi Takaki, Yui Yoshida, Yasuhiro Suzuki
  • Patent number: 8946322
    Abstract: Thermosetting resins are provided that are toughened with an irradiated thermoplastic toughening agent and which have reduced levels of solvent-induced micro crack formation. The thermoplastic toughening agent is treated with a sufficient amount of high-energy radiation (e.g. electron beam or gamma rays) to cause a reduction in solvent-induced micro crack formation in the cured resin when compared to the same toughened thermosetting resin in which the non-irradiated version of the thermoplastic toughening agent is used.
    Type: Grant
    Filed: April 14, 2008
    Date of Patent: February 3, 2015
    Assignee: Hexcel Composites Ltd
    Inventors: John L. Cawse, Stephen Mortimer, Chrisopher J. Wade
  • Patent number: 8946358
    Abstract: A method for accelerating the curing of a polyarylene sulfide. The polyarylene sulfide is blended with a cure accelerator to form a mixture where the weight percentage of accelerator is between 0.2% and 15.0% of the total weight of the blend. The mixture is cured at 320° C. or above for at least 20 minutes. The cure accelerator is a compound selected from the group consisting of ionomers, hindered phenols, polyhydric alcohols, polycarboxylates, and mixtures of the foregoing.
    Type: Grant
    Filed: March 22, 2011
    Date of Patent: February 3, 2015
    Assignee: E I du Pont de Nemours and Company
    Inventors: Joel M Pollino, Joachim C Ritter
  • Patent number: 8921513
    Abstract: Methods for forming a low chlorine content washed polyarylene sulfide are described. Methods include washing a polyarylene sulfide that includes aryl halide endgroups with a solution that includes a disulfide compound. The solution can also include a catalyst and an organic solvent. During the disulfide wash, a nucleophilic substitution reaction occurs between the disulfide compound and aryl halides endgroups of the polyarylene sulfide. The nucleophilic substitution reaction is carried out at conditions to prevent chain scission of the polyarylene sulfide that includes the aryl halide endgroups. Compositions and products formed with the low chlorine content disulfide washed polyarylene sulfide are also described.
    Type: Grant
    Filed: September 18, 2012
    Date of Patent: December 30, 2014
    Assignee: Ticona LLC
    Inventors: Rong Luo, Xinyu Zhao
  • Patent number: 8901257
    Abstract: Flexible members for use in imaging devices comprise a polyphenylsulfone and a polyetherimide; and optionally, a polysiloxane surfactant.
    Type: Grant
    Filed: February 12, 2011
    Date of Patent: December 2, 2014
    Assignee: Xerox Corporation
    Inventor: Jin Wu
  • Patent number: 8895667
    Abstract: Methods are provided for making reversible crosslinked polymers. Exemplary methods comprise reacting first and second thermoplastic polymers having non-hindered olefins in the presence of a metathesis catalyst under conditions sufficient to form a crosslinked polymer. In certain embodiments, the methods comprise providing a crosslink promoting additive to improve the strength of the crosslinked polymer. In some embodiments, the methods comprise decrosslinking a crosslinked polymer through a metathesis or an ozonolysis reaction.
    Type: Grant
    Filed: July 17, 2009
    Date of Patent: November 25, 2014
    Assignee: Tyco Electronics Corporation
    Inventors: Mark W. Ellsworth, Stefanie M. Gravano-Doerffler
  • Publication number: 20140343215
    Abstract: There is provided a polyphenylene sulfide resin composition, comprising 5 to 95% by weight of a component (B) which is a polyphenylene sulfide resin having a weight-average molecular weight of not less than 10,000 and a weight loss percentage ?Wr of not greater than 0.18% under heating, relative to 95 to 5% by weight of a component (A) which is a polyphenylene sulfide resin having the weight loss percentage ?Wr of greater than 0.18%, wherein a total of the component (A) and the component (B) is equal to 100% by weight.
    Type: Application
    Filed: December 26, 2012
    Publication date: November 20, 2014
    Inventors: Naoya Ouchiyama, Shunsuke Horiuchi, Hideki Matsumoto, Kei Saitoh
  • Publication number: 20140343235
    Abstract: Disclosed is an aluminum-polymer resin composite. The composite includes i) aluminum and ii) a polymer resin bonded to the aluminum after modification of the aluminum surface with at least one surface modifier selected from the group consisting of sulfur-containing diazole derivatives, sulfur-containing diamine derivatives, sulfur-containing thiol derivatives, sulfur-containing pyrimidine derivatives, and sulfur-containing silane coupling agents. The intensity ratios of C/Al, N/Al, O/Al, Na/Al, Si/Al, and S/Al in the composite are in the range of 9.75×10?6 to 9.5×10?1 at depths of 100 nm to 500 nm, as analyzed by secondary ion mass spectrometry (SIMS). The composite has improved adhesive strength between the metal and the resin while maintaining its tensile strength and air tightness even after thermal shock testing.
    Type: Application
    Filed: March 20, 2013
    Publication date: November 20, 2014
    Inventors: Euh Duck Jeong, Eun Kyung Jang, Tae Eun Hong, Mi Rang Byeon, Jong Pil Kim, Jong Seong Bae, Jong Sung Jin, Hong Dae Jung, Su Jong Lee
  • Publication number: 20140309354
    Abstract: Thermoplastic compositions that incorporate a polyarylene sulfide and exhibit reduced volatility are described. Methods for forming the thermoplastic composition are also described as are products that can incorporate the compositions. A formation method can include melt processing the composition and incorporating a molecular sieve in the composition downstream of the addition point for the polyarylene sulfide as well as downstream of additives that could interact with the molecular sieve such as coupling agents.
    Type: Application
    Filed: April 4, 2014
    Publication date: October 16, 2014
    Applicant: Ticona LLC
    Inventors: Ke Feng, Paul Yung
  • Publication number: 20140228527
    Abstract: Provided are methods for obtaining modified polyarylene sulfide compositions having improved thermal and thermo-oxidative stability, the compositions so obtained, and articles comprising the compositions. The method comprises the steps of contacting, in the presence of a suitable solvent, a polyarylene sulfide with at least one reducing agent and at least base to form a first mixture. The reducing agent comprises zinc(0), tin(0), tin(II), bismuth (0), bismuth(III), or a combination thereof. The first mixture is heated to form a second mixture in which the polyarylene sulfide is dissolved. The polyarylene sulfide is then precipitated to obtain a modified polyarylene sulfide.
    Type: Application
    Filed: September 21, 2012
    Publication date: August 14, 2014
    Inventors: Robert John Duff, Zheng-Zheng Huang, Joachim C. Ritter, Joel M. Pollino
  • Patent number: 8796399
    Abstract: Polyethersulfones having Tg greater than about 225° C. and a notched Izod value greater than about 1 ft-lb/in, as measured by ASTM D256, comprise from about 5 mol % to less than about 40 mol % structural units of formula 1; and from greater than about 60 mol % to about 95 mol % structural units of formula 2 wherein R1, R2, and R3 are independently at each occurrence a halogen atom, a nitro group, a cyano group, a C1-C12 aliphatic radical, C3-C12 cycloaliphatic radical, or a C3-C12 aromatic radical; n, m, q are independently at each occurrence integers from 0 to 4; and Q is a C3-C20 cycloaliphatic radical, or a C3-C20 aromatic radical.
    Type: Grant
    Filed: January 30, 2012
    Date of Patent: August 5, 2014
    Assignee: Sabic Innovative Plastics IP B.V.
    Inventors: Daniel Joseph Brunelle, Daniel Steiger
  • Patent number: 8796392
    Abstract: A method for injection molding a thermoplastic composition that contains a polyarylene sulfide and an aromatic amide oligomer is provided. Due to the improved crystallization properties imparted by the oligomer, the present inventors have discovered that the thermoplastic composition can be molded at lower temperatures to still achieve the same degree of crystallization. In addition to minimizing the energy requirements for the molding operation, such low mold temperatures may be accomplished using heating mediums that are less corrosive and expensive than some conventional techniques.
    Type: Grant
    Filed: December 10, 2012
    Date of Patent: August 5, 2014
    Assignee: Ticona LLC
    Inventors: Rong Luo, Xinyu Zhao
  • Patent number: 8785571
    Abstract: A reactive functional group-containing polyarylene sulfide being narrow in dispersity and little in gas generation amount is produced by heating a cyclic polyarylene sulfide composition in the presence of 0.1 mol % to 25 mol %, per mol of arylene sulfide structural units, of a sulfide compound having a reactive functional group selected from among an amino group, a carboxyl group, a hydroxyl group, an acid anhydride group, an isocyanate group, an epoxy group, a silanol group, and an alkoxysilane group.
    Type: Grant
    Filed: October 28, 2011
    Date of Patent: July 22, 2014
    Assignee: Toray Industries, Inc.
    Inventors: Akinori Kanomata, Shunsuke Horiuchi, Shu Kaiho, Koji Yamauchi
  • 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: 20140097134
    Abstract: Provided are methods for obtaining modified polyarylene sulfide compositions having improved thermal and thermo-oxidative stability, the compositions so obtained, and articles comprising the compositions. The method comprises the steps of contacting, in the presence of a suitable solvent, a polyarylene sulfide with at least one reducing agent and at least base to form a first mixture. The reducing agent comprises zinc(0), tin(0), tin(II), bismuth (0), bismuth(III), or a combination thereof. The first mixture is heated to form a second mixture in which the polyarylene sulfide is dissolved. The polyarylene sulfide is then precipitated to obtain a modified polyarylene sulfide.
    Type: Application
    Filed: October 4, 2012
    Publication date: April 10, 2014
    Applicant: E I DUPONT DE NEMOURS AND COMPANY
    Inventors: ROBERT John DUFF, Zheng-Zheng Huang, Joel M. Pollino, Joachim C. Ritter
  • 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: 8648155
    Abstract: The present description discloses a polymeric composition which is a melt-processed alloy comprised of (a) a polyarylene sulfide resin, (b) a polyaryl-ether-ketone resin, and a reactive compound which results in (c) a graft copolymer of the polyarylene sulfide resin and/or the polyaryl-ether-ketone resin in addition to the starting resins. Exemplary melt-processed polymeric compositions can be made by reacting an alkoxy silane with the polyarylene sulfide resin and/or the polyaryl-ether-ketone resin to produce a graft copolymer of a portion of one or both of the resins, sufficient to render the composition uniform and homogeneous. It is normally preferred for the exemplary organosilane compound, to be an amino silane. The subject invention further reveals an insulated wire comprising (1) an electrical conductor and (2) a layer of the melt-processed alloy composition; and fiber reinforced composites comprising fibers substantially fully impregnated with the alloy polymeric composition.
    Type: Grant
    Filed: April 27, 2012
    Date of Patent: February 11, 2014
    Assignee: Ticona LLC
    Inventors: Manoj Ajbani, Andrew Auerbach, Ke Feng
  • Patent number: 8623971
    Abstract: Polyethersulfones having Tg greater than about 225° C. and a notched Izod value greater than about 1 ft-lb/in, as measured by ASTM D256, comprise from about 5 mol % to less than about 40 mol % structural units of formula 1; and from greater than about 60 mol % to about 95 mol % structural units of formula 2 wherein R1, R2, and R3 are independently at each occurrence a halogen atom, a nitro group, a cyano group, a C1-C12aliphatic radical, C3-C12cycloaliphatic radical, or a C3-C12aromatic radical; n, m, q are independently at each occurrence integers from 0 to 4; and Q is a C3-C20cycloaliphatic radical, or a C3-C20aromatic radical.
    Type: Grant
    Filed: January 30, 2012
    Date of Patent: January 7, 2014
    Assignee: Sabic Innovative Plastics IP B.V.
    Inventors: Daniel Joseph Brunelle, Daniel Steiger
  • Publication number: 20140005304
    Abstract: A nanocomposite comprises: a polymer; and a nanofiller disposed in the polymer, the nanofiller comprising a first nanoparticle bonded to a second nanoparticle. A process of making a nanocomposite comprises: combining a silsesquioxane and a nanoparticle; bonding the nanoparticle to the silsesquioxane to make a nanofiller; and dispersing the nanofiller in a polymer to make the nanocomposite.
    Type: Application
    Filed: July 2, 2012
    Publication date: January 2, 2014
    Applicant: BAKER HUGHES INCORPORATED
    Inventors: Radhika Suresh, Soma Chakraborty
  • 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
  • Publication number: 20130313780
    Abstract: An article includes a crosslinked product of: a first crosslinked polymer and a second crosslinked polymer, wherein the article has a gradient in glass transition temperature. A process for making the article includes combining a first crosslinked polymer and a second crosslinked polymer to form a composition; compressing the composition; heating the composition; and crosslinking the composition to form the article, the article having a gradient in glass transition temperature. An article can be a seal that includes a first portion including a crosslinked product of: a first crosslinked polymer and a second crosslinked polymer; and a second portion including a polymer which is different than a constituent polymer in the first portion, wherein the seal has a gradient in glass transition temperature.
    Type: Application
    Filed: May 23, 2012
    Publication date: November 28, 2013
    Applicant: BAKER HUGHES INCORPORATED
    Inventors: Michael H. Johnson, Nicholas Carrejo
  • Patent number: 8546488
    Abstract: Cleavable, disulfide-coupled block copolymers as can be used in the preparation of nanoporous thin films, micellar configurations and related structures.
    Type: Grant
    Filed: May 25, 2012
    Date of Patent: October 1, 2013
    Assignee: University of Massachusetts
    Inventors: Sankaran Thayumanavan, Akamol Klaikherd, Suhrit Ghosh
  • Publication number: 20130253147
    Abstract: A production process of a poly(arylene sulfide), including (a) a polymerization step of polymerizing at least one sulfur source selected from the group consisting of alkali metal sulfides and alkali metal hydrosulfides and a dihalo-aromatic compound in an organic amide solvent to form a polymer; (b) a separation step of separating the polymer from a liquid reaction mixture containing the polymer formed after the polymerization step; (c) a washing step of washing the polymer with at least one washing liquid selected from the group consisting of water, an organic solvent and a mixed solution of water and an organic solvent as desired; and (d) an aqueous oxidizing solution treatment step of treating the polymer by bringing the polymer into contact with an aqueous oxidizing solution.
    Type: Application
    Filed: October 18, 2011
    Publication date: September 26, 2013
    Applicant: KUREHA CORPORATION
    Inventors: Yoshihiro Ichinose, Masanori Kobayashi, Takayuki Kimura, Koichi Suzuki
  • Publication number: 20130225771
    Abstract: A reactive functional group-containing polyarylene sulfide being narrow in dispersity and little in gas generation amount is produced by heating a cyclic polyarylene sulfide composition in the presence of 0.1 mol % to 25 mol %, per mol of arylene sulfide structural units, of a sulfide compound having a reactive functional group selected from among an amino group, a carboxyl group, a hydroxyl group, an acid anhydride group, an isocyanate group, an epoxy group, a silanol group, and an alkoxysilane group.
    Type: Application
    Filed: October 28, 2011
    Publication date: August 29, 2013
    Applicant: Toray Industries, Inc.
    Inventors: Akinori Kanomata, Shunsuke Horiuchi, Shu Kaiho, Koji Yamauchi
  • Publication number: 20130196104
    Abstract: The present invention provides a thermoplastic resin composition, which is excellent in low-temperature toughness and high-temperature creep characteristics, by a method for producing a thermoplastic resin composition by melt-kneading: (a) a polyphenylene sulfide resin, with (b) a polyetherimide resin or a polyethersulfone resin, wherein the thermoplastic resin composition contains 99 to 1% by weight of the component (a) and 1 to 99% by weight of the component (b) based on 100% by weight of the total amount of the component (a) and the component (b); the melt-kneading step is the step of melt-kneading by an extruder provided with an elongational flow zone which is a zone in which melt-kneading is performed while being allowed to undergo elongational flow; and a flow effect pressure drop before and after the elongational flow zone is from 50 to 1,000 kg/cm2.
    Type: Application
    Filed: October 18, 2011
    Publication date: August 1, 2013
    Applicant: TORAY INDUSTRIES, INC.
    Inventors: Hideki Matsumoto, Kei Saito, Naoya Nakamura
  • Patent number: 8492474
    Abstract: Methods of making miscible and compatible immiscible polymer blends are disclosed. The polymer blends have a polyimide as a component. The miscible polymer blends have a single glass transition temperature. The compatible polymer blends have two glass transition temperatures. The polymer blends may optionally include one or more fillers.
    Type: Grant
    Filed: April 9, 2008
    Date of Patent: July 23, 2013
    Assignee: Sabic Innovative Plastics IP B.V.
    Inventors: Robert Russell Gallucci, Tara J. Mullen, Roy Ray Odle, Kapil Chandrakant Sheth, James Mitchell White
  • Publication number: 20130158212
    Abstract: A method for injection molding a thermoplastic composition that contains a polyarylene sulfide and an aromatic amide oligomer is provided. Due to the improved crystallization properties imparted by the oligomer, the present inventors have discovered that the thermoplastic composition can be molded at lower temperatures to still achieve the same degree of crystallization. In addition to minimizing the energy requirements for the molding operation, such low mold temperatures may be accomplished using heating mediums that are less corrosive and expensive than some conventional techniques.
    Type: Application
    Filed: December 10, 2012
    Publication date: June 20, 2013
    Applicant: TICONA LLC
    Inventor: Ticona LLC
  • Publication number: 20130131210
    Abstract: A composition includes a crosslinked product of a polyphenylene sulfide and a polyphenylsulfone. A method for the manufacture of the crosslinked product of a polyphenylene sulfide and a polyphenylsulfone includes heating the polyphenylene sulfide and the polyphenylsulfone in presence of a crosslinking agent at a temperature and for a time effective to form the crosslinked product of polyphenylene sulfide and polyphenylsulfone.
    Type: Application
    Filed: November 23, 2011
    Publication date: May 23, 2013
    Applicant: BAKER HUGHES INCORPORATED
    Inventors: David P. Gerrard, Jiaxiang Ren, Ping Duan