Inorganic Sulfur Reactant Contains At Least One Metal Atom Or Contains An Ammonium Ion Patents (Class 528/388)
  • Patent number: 6242501
    Abstract: A process is provided to recover poly(arylene) sulfide from a poly(arylene) sulfide reaction mixture. In particular, a process is provided to recover poly(arylene) sulfide utilizing at least one extraction agent followed by vacuum drying.
    Type: Grant
    Filed: December 2, 1998
    Date of Patent: June 5, 2001
    Assignee: Phillips Petroleum Company
    Inventors: Richard A. Green, Jon F. Geibel
  • Patent number: 6201100
    Abstract: The present invention pertains to electroactive, energy-storing, highly crosslinked organic polymers and copolymers with a carbocyclic repeat unit comprising a non-aromatic carbocycle with from 3 to 12 ring carbon atoms, wherein each repeat unit is covalently linked via divalent polysulfide linkages having the formula, —Sm—, where m is the same or different at each occurrence and is an integer from 3 to 10. The present invention also pertains to methods of making such polymers and copolymers, which methods generally comprise reacting an alkali metal polysulfide with a halogen-substituted carbocyclic precursor.
    Type: Grant
    Filed: December 19, 1997
    Date of Patent: March 13, 2001
    Assignee: Moltech Corporation
    Inventors: Alexander Gorkovenko, Terje A. Skotheim
  • Patent number: 6153725
    Abstract: The present invention is directed to methods of fabricating electrically conducting polymers and precursors thereof in which the polymer has a controlled level of aggregation and morphology. This is done by controlling the rate of polymerization and the rate at which the polymer precipitates from solution during the polymerization reaction. An additive is added to the polymerization medium, said additive increasing or decreasing the rate at which the polymer precipitates from the reaction medium. When said additive is a second organic solvent, the polymerization reaction proceeds homogeneously for a longer period of time than does the corresponding polymerization reaction which does not include said additive. Control of the polymerization kinetics allows control of the morphology for the isolated polymer and in turn control of the properties of these polymers.
    Type: Grant
    Filed: July 17, 1998
    Date of Patent: November 28, 2000
    Assignee: International Business Machines Corporation
    Inventors: Marie Angelopoulos, Richard Anthony DiPietro
  • Patent number: 6150498
    Abstract: Methods for devolatilizing polymer solutions have been invented which include, in certain aspects, dissolving a viscous polymer in a solvent forming a polymer-solvent solution, introducing the polymer-solvent solution into a thermal dryer, heating or cooling the polymer-solvent solution in the thermal dryer forming product polymer with solvent removed and separated solvent (which may include other residuals), the separated solvent with other residuals if present vaporizing in the thermal dryer forming a vapor, removing the vapor from the thermal dryer, and discharging product polymer from the thermal dryer.
    Type: Grant
    Filed: July 3, 1997
    Date of Patent: November 21, 2000
    Assignees: The Dow Chemical Company, E. I. du Pont de Nemours and Company
    Inventors: Richard C. Abel, Jr., Michael E. Rowland, Robert B. Combs, Jerry W. Soape, Stanley W. Smith
  • Patent number: 6093319
    Abstract: A process is provided for making a composition said process comprising mixing about 60% by weight to about 90% by weight of a first P(AS) having a melt flow index of about 120 grams/10 minutes or more and about 10% by weight to about 40% by weight of a second P(AS) having a melt flow index of about 110 grams/10 minutes or less. In another embodiment of this invention, said composition and manufactures produced from said composition are provided.
    Type: Grant
    Filed: December 18, 1998
    Date of Patent: July 25, 2000
    Assignee: Phillips Petroleum Company
    Inventors: David A. Soules, Jon F. Geibel, Aubrey South, Jr.
  • Patent number: 6077918
    Abstract: Phosphonium ionomers which, as random copolymers, are composed of the units (1) and (2) ##STR1## in which Ar-- is a phenylene radical or a biphenylene, naphthylene or anthrylene radical or another divalent aromatic radical and may be different units within the polymer chain;--X-- is an --S--, --SO-- and/or --SO.sub.2 -- unit,where --X-- within the polymer chain may be up to 3 different units;Z is a monovalent or polyvalent opposite ion;Ph is a phenyl radical;m is the charge of the opposite ionand the average degree of polymerization is in the range from 3 to 2000.The polymers can be used for the production of membranes, in particular for electrochemical cells.
    Type: Grant
    Filed: December 23, 1997
    Date of Patent: June 20, 2000
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Helmut Witteler
  • Patent number: 6020442
    Abstract: Oxidation product of polyarylene sulfides comprising recurring units of the formula.brket open-st.C.sub.6 H.sub.4 --S.brket close-st. (I)in the form of a compound comprising recurring units of the formula.brket open-st..paren open-st.C.sub.6 H.sub.4 --S.paren close-st..sub.a .paren open-st.C.sub.6 H.sub.4 --SO.paren close-st..sub.b .brket close-st.(II)in which the sulfur/oxygen ratio is from 1:0.1 to 1:1, the sum of a and b always being 1 and a and b each being greater than zero or with the proviso that a is zero if b is 1.
    Type: Grant
    Filed: January 11, 1996
    Date of Patent: February 1, 2000
    Assignee: Ticona GmbH
    Inventors: Dietrich Fleischer, Heinz Strutz, Jurgen Kulpe, Andreas Schleicher
  • Patent number: 6015870
    Abstract: Polysulfide silanes: (RO).sub.3 SiC.sub.3 H.sub.6 S.sub.x C.sub.3 H.sub.6 Si(OR).sub.3 are reacted with an anhydrous sulfur compound: M.sup.1.sub.2 S or M.sup.2 S and a halogenoalkoxysilane: XC.sub.3 H.sub.6 Si(OR).sub.3 to form polysulfide silanes: (RO).sub.3 SiC.sub.3 H.sub.6 S.sub.y C.sub.3 H.sub.6 Si(OR).sub.3 wherein R is methyl or ethyl, x is a positive number of 3 to 6 on the average, M.sup.1 is an alkali metal or ammonium, M.sup.2 is an alkaline earth metal or zinc, X is a halogen, and y is a positive number less than x on the average. Short chain polysulfide silanes can be prepared with the industrial advantages of safety, high yields and low cost.
    Type: Grant
    Filed: September 28, 1998
    Date of Patent: January 18, 2000
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Shoji Ichinohe, Hideyoshi Yanagisawa, Akira Yamamoto
  • Patent number: 6001934
    Abstract: A simple and convenient process is provided to introduce a sufficient quantity of functional groups to a main chain or terminals of the chain of a polyarylene sulfide resin to improve properties of the resin.The invention provides a process for heat oxidation crosslinking a polyarylene sulfide resin, characterized by conducting the heat oxidation crosslinking reaction in the presence of at least one organic compound having at least one active-hydrogen-containing group or at least one organic compound having at least one active-hydrogen-containing group and a group derived from an active hydrogen containing group by substituting an active hydrogen of the active hydrogen containing group with an alkali metal, to thereby prepare a functional group-containing polyarylene sulfide resin.
    Type: Grant
    Filed: September 1, 1998
    Date of Patent: December 14, 1999
    Assignee: Tonen Chemical Co.
    Inventors: Hidenori Yamanaka, Osamu Komiyama
  • Patent number: 5973098
    Abstract: The polymerizable compositions compriseA) at least one polyiso(thio)cyanate monomer, and at least one polythiol monomer; or at least one episulfide compound and optionally one or more compounds having two or more functional groups capable of reacting with episulfide groups; andB) an effective amount of a thiocyanate salt as a polymerization catalyst.Application to the fabrication of optical articles, such as lenses.
    Type: Grant
    Filed: October 29, 1998
    Date of Patent: October 26, 1999
    Assignee: Essilor International - Compagnie Generale D'Optique
    Inventors: Gabriel Keita, Pamela Anne McClimans, Steve Weber, Yassin Turshani
  • Patent number: 5969032
    Abstract: The invention relates to an emulsion polymerization process for preparing a latex binder for use in paint. The process involves reacting a water-soluble or water-dispersible polymerizable surfactant having a terminal allyl amine moiety with at least one ethylenically unsaturated monomer and ionic monomer at a pH from about 2 to about 7. Significantly lower levels of the polymerizable surfactants are required to control the latex particle size and to stabilize the latex particles at high solids content as compared to the amount of conventional anionic surfactants used to stabilize a latex.
    Type: Grant
    Filed: March 9, 1998
    Date of Patent: October 19, 1999
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventors: Lien Phan, Rajeev Farwaha
  • Patent number: 5945490
    Abstract: Polyarylene sulfide (PAS) is disclosed, of which extract with methylene chloride is in an amount of not more than 0.7% by weight, a melt viscosity V.sub.6 is 20 to 15,000 poises and a content of --SX groups is at least 15 micro moles/g, wherein X represents an alkali metal or a hydrogen atom. The PAS is prepared as follows: an alkali metal sulfide is reacted with a dihaloaromatic compound in an organic amide solvent, while a part of a gaseous phase in a reactor is condensed by cooling a gaseous phase part of the reactor to return the condensed liquid to a liquid phase; and the polyarylene sulfide thus prepared is washed with an organic solvent and then with water. The present invention also provides a composition comprising 100 parts by weight of (A) the aforesaid PAS and 0.01 to 5.0 parts by weight of (B) at least a silane compound selected from the group consisting of methacryloxysilane compounds, ureidosilane compounds and epoxy silane compounds.
    Type: Grant
    Filed: November 10, 1997
    Date of Patent: August 31, 1999
    Assignee: Tonen Chemical Corporation
    Inventors: Takashi Tsuda, Osamu Komiyama
  • Patent number: 5929203
    Abstract: A process is provided for producing a high molecular weight poly(arylene sulfide) polymer employing at least one dihaloaromatic compound, a sulfur source, a polar organic compound, a lithium salt which is soluble in the polar organic compound, and water in an amount less than about 1.75 moles of water per mole of sulfur under polymerization conditions. The pressure and temperature are chosen to allow the volatile reactants to be maintained in liquid form in the reaction mixture.
    Type: Grant
    Filed: October 23, 1992
    Date of Patent: July 27, 1999
    Assignee: Phillips Petroleum Company
    Inventors: Carlton E. Ash, Jon F. Geibel, Harold D. Yelton
  • Patent number: 5907029
    Abstract: The invention relates to polyarylene sulfoxides which are soluble in polar organic solvents, a process for their preparation and their use. Soluble polyarylene sulfoxides can be prepared by homogeneous partial oxidation of polyarylene sulfides. The homogeneous partial oxidation is achieved by dispersing the polyarylene sulfide in finely divided form in a solvent stable to oxidation, slowly adding a mild oxidizing agent and terminating the oxidation as soon as the polymer chains have reached a uniform degree of oxidation. The partially oxidized polyarylene sulfoxides are suitable for the production of coatings and shaped articles, such as fibers, membranes, films and nonwovens.
    Type: Grant
    Filed: September 16, 1997
    Date of Patent: May 25, 1999
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Stefan Disch, Michael Haubs, Axel Schonfeld, Helmut Scheckenbach
  • Patent number: 5905137
    Abstract: The present invention relates to a process for preparing sulfur-containing polymers from at least one sulfide and at least one aromatic dihalo compound in a solvent, which comprisesa) reacting the sulfide with a stoichiometric excess of aromatic dihalo compound,b) largely removing the excess aromatic dihalo compound andc) further polymerizing the mixture.
    Type: Grant
    Filed: November 19, 1996
    Date of Patent: May 18, 1999
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Michael Haubs, Reinhard Wagener, Afif Nesheiwat
  • Patent number: 5898061
    Abstract: This invention provides a method for producing polyarylene sulfide continuously, comprising; 1) polymerization step wherein polyarylene sulfide is polymerized from a sulfur compound in the liquid or gas state and a dihalogenated aromatic compound in non-protonic organic solvent, 2) separation step wherein mixture of the polymerization solution and the washing solution is separated into the polymer phase and the solvent phase, and in said separation step said polymer phase is continuously taken out in the liquid state. The method of this invention makes it possible to produce polyarylene sulfide of high purity that it is suitable for molding and injection molding of the seat, the film, the fiber, etc. for the electronic and electric material field etc., with high-molecular-weight and low content of by-products, efficiently and economically.
    Type: Grant
    Filed: November 26, 1997
    Date of Patent: April 27, 1999
    Assignees: Idemitsu Petrochemical Co., Ltd., Petroleum Energy Center (PEC)
    Inventors: Kiyoshi Sase, Yoshinari Koyama, Masao Oomori
  • Patent number: 5894072
    Abstract: In a process for preparing aromatic sulfur-containing polymers, the polymer is formed from a prepolymer having halogen end groups. During preparation of the prepolymers, an alkali equivalent and a sulfur equivalent in a ratio of 0.5 to 1:1 is employed in the reaction mixture. The two-step process is particularly suitable for preparing polyphenylene sulfide.
    Type: Grant
    Filed: March 21, 1997
    Date of Patent: April 13, 1999
    Assignee: Hoechst Aktiengelesellschaft
    Inventors: Michael Haubs, Reinhard Wagener
  • Patent number: 5891987
    Abstract: A copolyamide composition prepared from hexamethylene diamine and either mixtures of adipic acid and terephthalic acid, or mixtures of adipic acid, terephthalic acid and isophthalic acid, has a melting point below 320.degree. C., a glass transition temperature between 100.degree. C. and 120.degree. C. and physical properties similar to nylon 66.
    Type: Grant
    Filed: November 15, 1995
    Date of Patent: April 6, 1999
    Assignee: Industrial Technology Research Institute
    Inventors: Wu-Bin Yuo, Chien-Shiun Liao, Wen-Jeng Lin, Li-Kuei Lin, Tien-San Lee, Szu-Yuan Chan
  • Patent number: 5886130
    Abstract: A new class of polyarylene co-polymers include repeating units comprising one or more arylene units having the general formula (--Ar--/--Y--).sub.n, where Y is a divalent group chosen from nil, --Z--, --Z--Ph--, and --Ph--Z--Ph--, where Z is a divalent group chosen from the group consisting of --O--, --S--, --NR--, --O(CO)--, --O(CO.sub.2)--,--(CO)NH(CO)--, --NR(CO)--, phthalimide, pyromellitimide, --CO--, --SO--, --SO.sub.2 --, --P(O)R--, --CH.sub.2 --, --CF.sub.2 --, and --CRR'--; Ph is phenylene (ortho, meta or para); and n is greater than 4. The co-polymers are useful as molding resins, and composite matrix resins, and where Ar is heteroarylene as ion exchange resins.
    Type: Grant
    Filed: November 2, 1995
    Date of Patent: March 23, 1999
    Assignee: Maxdem Incorporated
    Inventors: Mark S. Trimmer, Ying Wang, Matthew L. Marrocco III, Virgil J. Lee
  • Patent number: 5880253
    Abstract: A process for producing a polymer is provided which can comprise, consist essentially of, or consists of, contacting an inorganic compound having the formula of M.sub.x H.sub.y Z.sub.p, in an aqueous medium, with an organic halide under a condition sufficient to effect the production of the polymer in which the polymer comprises repeat units having the formula of (C.sub.m H.sub.2m-q (R'.sub.q)--Z.sub.p).sub.n in which m is a whole number from 1 to about 20; Z can be S, Se, or combinations thereof; n is a number from about 5 to about 400; M is a metal or ammonium ion; x is a number filling the necessary valency of M; y is 0 or 1; q is a whole number from 0 to about 10 and p is a whole number from 1 to 4.
    Type: Grant
    Filed: March 24, 1997
    Date of Patent: March 9, 1999
    Assignee: Phillips Petroleum Company
    Inventor: James E. Shaw
  • Patent number: 5856433
    Abstract: An apparatus for manufacturing polyarylene sulfide is disclosed. At least the major part of the apparatus which comes into contact with liquid materials is made of the alloy containing nickel and chromium as essential components, or the two phase stainless steel, possessing the following characteristics (A) and/or (B):The characteristic (A): the characteristic of exhibiting a degree of surface corrosion of 3 .mu.m/y or less when immersed in a 3.6 mol/kg solution of lithium hydrosulfide in a non-proton organic solvent at 130.degree. C. for 90 days, while this solution is replaced with a fresh solution once every 30 days.The characteristic (B): the characteristic of exhibiting a degree of surface corrosion of 10 .mu.m/y or less when immersed in a 3.6 mol/kg solution of lithium chloride in a non-proton organic solvent at 260.degree. C. for 90 days, while this solution is replaced with a fresh solution once every 30 days.
    Type: Grant
    Filed: April 16, 1997
    Date of Patent: January 5, 1999
    Assignee: Idemitsu Petrochemical Co., Ltd.
    Inventors: Yoshinari Koyama, Kiyoshi Sase
  • Patent number: 5840830
    Abstract: The invention provides a process for producing a poly(arylene sulfide) comprising a dehydration step of heating and dehydrating a mixture containing an organic amide solvent (a), an alkali metal sulfide and water to control a water content in the mixture and a subsequent polymerization step of subjecting the alkali metal sulfide and a dihalo-aromatic compound to a polymerization reaction in the organic amide solvent (a), wherein hydrogen sulfide vaporized off during the dehydration step is absorbed in another organic amide solvent (b) outside a system in which the dehydration step is carried out, thereby recovering it, and the hydrogen sulfide thus recovered is reused in the polymerization reaction as a raw material for the alkali metal sulfide. The production process of the invention can solve various problems attendant upon the vaporization of hydrogen sulfide and provide a poly(arylene sulfide) which undergoes little variation in melt viscosity and has stable quality.
    Type: Grant
    Filed: February 11, 1997
    Date of Patent: November 24, 1998
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Michihisa Miyahara, Hiroyuki Sato, Yoshikatsu Satake
  • Patent number: 5824767
    Abstract: A process for improving the processability of poly(arylene sulfide) in melt spinning operations by treatment with a barium-containing compound and, optionally, a lubricant is disclosed.
    Type: Grant
    Filed: July 8, 1996
    Date of Patent: October 20, 1998
    Assignee: Hoechst Celanese Corporation
    Inventors: Balaram B. Gupta, Andrew B. Auerbach, Barrie L. Davies
  • Patent number: 5804100
    Abstract: Deaggregated substituted and unsubstituted polyparaphenylenes, polyparaphenylevevinyles, polyanilines, polyazines, polythiophenes, poly-p-phenylene sulfides, polyfuranes, polypyrroles, polyselenophene, polyacetylenes formed from soluble precursors and combinations thereof and copolymers thereof and methods of fabrication are described. The deaggregated polymer molecules when subsequently doped show higher electrical conductivity. Agents such as lithium chloride, m-cresol and nonylphenol are used to deaggregate the polymer molecules. The deaggregating agents can be added prior to or during doping the molecules.
    Type: Grant
    Filed: January 9, 1995
    Date of Patent: September 8, 1998
    Assignee: International Business Machines Corporation
    Inventors: Marie Angelopoulos, Bruce K. Furman
  • Patent number: 5789533
    Abstract: A polyarylene sulfide in which a ratio of terminal --SX groups to a total of the terminal --SX groups and --SZn-- groups is less than 20 mole %, wherein X represents an alkali metal or a hydrogen atom, and which has a melt viscosity, V.sub.6 of 100 to 2,000 poises.Also disclosed are a composition comprising 100 parts of the above polyarylene sulfide, 0.01 to 20 parts of zeolite and 0.01 to 20 part of silica, and a process for the preparation of the above polyarylene sulfide.
    Type: Grant
    Filed: June 27, 1996
    Date of Patent: August 4, 1998
    Assignee: Tonen Chemical Corporation
    Inventors: Hidenori Yamanaka, Osamu Komiyama, Masaru Miyoshi, Yoshitaka Anazawa, Naohiro Mikawa, Kazuhiro Ichikawa
  • Patent number: 5780583
    Abstract: Crosslinkable poly(arylene sulfide) oligomers are prepared by reaction of a dihaloaromatic compound, a sulfur compound that is reactive with halo organic compounds to form thioethers, and an end cap monomer corresponding to the formula:A.sub.i --Ar--Xwhere A is an alpha, beta-unsaturated hydrocarbon moiety that is subject to step growth reaction by chemical activation, or by thermal activation at temperatures substantially in excess of the temperature of formation of the oligomer. Both linear and multidimensional oligomers are disclosed.
    Type: Grant
    Filed: January 9, 1991
    Date of Patent: July 14, 1998
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 5777069
    Abstract: A tubular extrusion molding product comprising a high molecular weight polyarylene sulfide having a melt viscosity of from 3,100 poise to 60,000 poise produced by reacting an alkali metal sulfide and a dihaloaromtic compound in the presence of an organic amide solvent, cooling a gaseous phase part in the reaction zone during the reaction thereby condensating at least a part of the gaseous phase and refluxing the resultant condensate to a liquid phase in the reaction zone. A tubular extrusion molding product having further improved impact resistance can be provided by copolymerizing from 0.2 mol % to 1 mol % of a polyhaloaromatic compound to the alkali metal sulfide. A tubular extrusion molding product of improved impact resistance is provided by further applying a heat treatment of the polyarylene sulfide intermediate product thereby increasing the melt viscosity.
    Type: Grant
    Filed: June 5, 1996
    Date of Patent: July 7, 1998
    Assignee: Tonen Chemical Corporation
    Inventors: Takashi Tsuda, Hidenori Yamanaka, Osamu Komiyama
  • Patent number: 5756654
    Abstract: Disclosed is a process for manufacturing polyarylene sulfide comprising pre-polymerizing a dihalogeno-aromatic compound with a liquid or gaseous sulfur compound in the presence of a lithium compound in an aprotic organic solvent followed by further polymerizing the resulting pre-polymerized system; which is characterized in that sufficient water is added to the pre-polymerized solution (I) to separate it into a tick polymer phase and a solvent phase, then a solvent is added to the thus-separated, thick polymer phase and the resulting polymer phase is further polymerized, for efficiently manufacturing high-purity polyarylene sulfide. The process does not require any complicated steps of washing the polymer with a multi-stage washing system and is free from the increase in the production costs of the polymer. In the process, the lithium salt used can be recovered efficiently.
    Type: Grant
    Filed: August 21, 1996
    Date of Patent: May 26, 1998
    Assignee: Idemitsu Petrochemical Co., Ltd.
    Inventors: Kiyoshi Sase, Kohji Namiki, Tetsuro Takeya
  • Patent number: 5744576
    Abstract: In a process for producing poly(phenylene sulfide), in which an alkali metal sulfide is reacted with a dihalo-aromatic compound in an organic amide solvent, the reaction is conducted through the following Steps 1 and 2, thereby efficiently providing granular, high-molecular weight poly(phenylene sulfide) having excellent whiteness in a short period of time and at a high yield. Step 1: a step comprising reacting the alkali metal sulfide with the dihalo-aromatic compound within a temperature range of 170.degree.-270.degree. C. in the organic amide solvent containing water in a proportion of 0.5-2.0 moles per mole of the alkali metal sulfide charged while raising the reaction temperature at an average heating rate of 0.1.degree.-1.degree. C./min in at least a temperature range of from 220.degree. C. to 240.degree. C.
    Type: Grant
    Filed: July 7, 1997
    Date of Patent: April 28, 1998
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Michihisa Miyahara, Hiroyuki Sato, Yoshikatsu Satake
  • Patent number: 5712350
    Abstract: Process for oxidizing a polymer containing thioether groups, in which the polymer in solid form in a suspension medium is oxidized with ozone. The polymer obtained is suitable for the production of functional parts on which high demands are made.
    Type: Grant
    Filed: January 16, 1996
    Date of Patent: January 27, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Dietrich Fleischer, Heinz Strutz, Jurgen Kulpe, Andreas Schleicher
  • Patent number: 5688873
    Abstract: Electroconductive polymers having a chemical structure represented by, for example, the formula (I) ##STR1## wherein R.sup.1 and R.sup.2 independently represent H, a C.sub.1 to C.sub.20 alkyl or alkoxy group, an amino group, a trihalomethyl group or a phenyl group, X represents S, O, Se, Te or NR.sub.3 R.sub.3 represents H, a C.sub.1 to C.sub.6 alkyl group or an aryl group, M represents a cation such as H.sup.+, an alkali metal ion or a quaternary ammonium ion, and m is 0.2 to 2 and a process for producing the polymer.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: November 18, 1997
    Assignee: Showa Denko K.K.
    Inventors: Yoshihiro Saida, Yoshiaki Ikenoue, Reiko Ichikawa
  • Patent number: 5688908
    Abstract: In the process for the preparation of aromatic sulfur-containing polymers, the polymer is formed from a prepolymer having halogen end groups. The process can be carried out in two stages: 1. Preparation of the prepolymer and 2. conversion of the prepolymer into the polymer. The process is particularly suitable for the preparation of polyphenylene sulfide.
    Type: Grant
    Filed: April 12, 1996
    Date of Patent: November 18, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Michael Haubs, Andreas Schleicher, Thorsten Niklas
  • Patent number: 5670569
    Abstract: Mixtures comprising polyarylene sulfides and polyarylene sulfoxides or partially oxidized polyarylene sulfides containing sulfoxide groups can be thermally crosslinked in a targeted manner depending on sulfoxide content. A process for producing crosslinked polyarylene sulfide moldings is based on the use of the mixtures in the thermal shaping.
    Type: Grant
    Filed: December 22, 1995
    Date of Patent: September 23, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Scheckenbach, Andreas Schleicher
  • Patent number: 5654383
    Abstract: The invention relates to polyarylene sulfides (PAS), preferably polyphenylene sulfide (PPS), reduced in viscosity by aftertreatment of the PAS formed in the production process with disulfides in the melt.
    Type: Grant
    Filed: June 30, 1994
    Date of Patent: August 5, 1997
    Assignee: Bayer AG
    Inventors: Burkhard Kohler, Klaus Kraft, Klaus Reinking, Bahman Sarabi, Wolfgang Ebert
  • Patent number: 5648453
    Abstract: Electroconductive polymers having a chemical structure represented by, for example, the formula (I) ##STR1## wherein R.sup.1 and R.sup.2 independently represent H, a C.sub.1 to C.sub.20 alkyl or alkoxy group, an amino group, a trihalomethyl group or a phenyl group, X represents S, O, Se, Te or NR.sub.3 R.sub.3 represents H, a C.sub.1 to C.sub.6 alkyl group or an aryl group, M represents a cation such as M.sup.+, an alkali metal ion or a quaternary ammonium ion, and m is 0.2 to 2 and a process for producing the polymer.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 15, 1997
    Assignee: Showa Denko K.K.
    Inventors: Yoshihiro Saida, Yoshiaki Ikenoue, Reiko Ichikawa
  • Patent number: 5605987
    Abstract: Disclosed herein is a process for the production of an alkylene thioether-arylene thioether copolymer, which comprises copolymerizably reacting a compound having at least one alkali thiolate group and obtained by causing an alkali metal sulfide to act on a poly(arylene thioether) in a water-containing polar organic solvent so as to depolymerize the poly(arylene thioether) with a dihalogen-substituted aliphatic compound in a water-containing polar organic solvent.
    Type: Grant
    Filed: July 8, 1992
    Date of Patent: February 25, 1997
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Yukichika Kawakami, Mitsuru Hoshino, Hiroyuki Sato
  • Patent number: 5554723
    Abstract: A process for the production of a poly(arylene thioether) containing phthalic anhydride groups wherein a dihalogen-substituted aromatic compound is reacted with an alkali metal sulfide in a polar organic solvent containing water to produce the poly(arylene thioether) is disclosed. This process comprises causing a monohalogen-substituted phthalic compound to exist in a polymerization reaction system, and controlling a ratio, a/b of the number of moles, a of the charged dihalogen-substituted aromatic compound to the number of moles, b of the charged alkali metal sulfide within a range of 0.8<a/b<1.
    Type: Grant
    Filed: March 19, 1993
    Date of Patent: September 10, 1996
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Naomitsu Nishihata, Shunzo Endo, Yukio Ichikawa, Takayuki Katto
  • Patent number: 5500474
    Abstract: Conductive polymers having repeating units of formula (II) ##STR1## formed by chemical or electrochemical oxidation of aniline derivatives of formula (I) ##STR2## wherein R.sub.1 denotes --(CH.sub.2).sub.n --; n is an integer between 2 and 12; R.sub.2, R.sub.3, R.sub.4 and R.sub.5 denote hydrogens or one or two of them can be a halogen atom, methyl, methoxy or nitro groups; and X denotes hydrogen an alkali metal ion, an ammonium ion, an alkyl ammonium ion or an anilinium ion. The conductive polymers have excellent stability toward electrochemical redox cyclization and good processibility.
    Type: Grant
    Filed: July 6, 1995
    Date of Patent: March 19, 1996
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Suh B. Rhee, Myong-Hoon Lee, Chang-Jin Lee, Bong S. Moon
  • Patent number: 5496917
    Abstract: Polyarylene thioethers having recurring units of the formula[--(S--E--).sub.a --(--SO--E--).sub.b --(SO.sub.2 --E).sub.c --](I)in which E are, independently of one another, phenylene, naphthylene or biphenylene, a and c have, independently of one another, values from 0 to less than 1 and b has values from greater than zero to less than 1, with the proviso that the sum of a+b+c is equal to 1 and at least two of the indices are greater than zero, are obtained by oxidation of polyarylene sulfides in two stages, wherein in the first stage a polymer in solid form in a suspension medium is oxidized with ozone and the reaction product obtained is in the second stage reacted in acetic acid with hydrogen peroxide in the presence of catalytic amounts of concentrated sulfuric acid and/or with addition of equilibrium per-acids. The polyarylene thioethers are suitable for the production of molded parts having high temperature resistance and high resistance to chemicals.
    Type: Grant
    Filed: May 3, 1994
    Date of Patent: March 5, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Dietrich Fleischer, Heinz Strutz, Ju/ rgen Kulpe, Andreas Schleicher
  • Patent number: 5496916
    Abstract: Process for preparing a polyarylene sulfone by oxidizing a polyarylene thioether in acetic acid with hydrogen peroxide, the reaction being carried out in the presence of catalytic amounts of concentrated sulfuric acid and/or with the addition of equilibrium per-acids. The reaction products are suitable for producing molded parts having high temperature resistance and high resistance to chemicals.
    Type: Grant
    Filed: May 3, 1994
    Date of Patent: March 5, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Dietrich Fleischer, Heinz Strutz, Ju/ rgen Kulpe, Andreas Schleicher
  • Patent number: 5493005
    Abstract: Alcohol-soluble, aromatic heterocyclic copolymers having repeating units of the formula: ##STR1## wherein x has a value of 0.10 to 0.90 and y has a value of 1.0-x. These copolymers are useful in the preparation of organic/inorganic hybrid materials having transparency which comprise the sol-gel derived, hydrolytically condensed reaction product of a metal alkoxide of the formula M(OR).sub.w wherein R is a lower alkyl group, M is Si, Ti, Al or a mixture thereof, and w is the valence value of M, and the above copolymer.
    Type: Grant
    Filed: February 21, 1995
    Date of Patent: February 20, 1996
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Fred E. Arnold, Jom P. Chen
  • Patent number: 5484876
    Abstract: Disclosed herein are an aromatic thioether ketone/thioether sulfone random copolymer comprising phenylene thioether ketone recurring units (I) and phenylene thioether sulfone recurring units (II), (a) the compositional ratio (I:II) of the recurring units (I) to the recurring units (II) ranging from 98:2 to 65:35, (b) the solution viscosity (.eta..sub.inh) being at least 0.3 dl/g, (c) the melt crystallization time (.tau.) being at least 3 minutes, (d) the melting point (Tm) being 300.degree.-350.degree. C., (e) the glass transition temperature being at least 125.degree. C., (f) the retention (400.degree. C./20 min) of melt crystallization enthalpy (.DELTA.Hmc) being at least 60%, and (g) the average particle size being at least 0.1 mm, and the production process thereof.
    Type: Grant
    Filed: July 29, 1994
    Date of Patent: January 16, 1996
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Yukichira Kawakami, Zenya Shiiki
  • Patent number: 5475081
    Abstract: A particle size of potyarylene sulfide obtained in polymerization is controlled by a process characterized in that a gaseous phase part of a reactor is cooled or heated after starting decreasing a temperature of a reaction system o an end of precipitation of polyarylene sulfide formed In an embodiment, a water content in the reaction system is 0.8 to 1.7 moles per mole of the alkali metal sulfide; the gaseous phase part of the reactor is cooled in a polymerization stage to thereby condense a part of a gaseous phase in the reactor and the condensed liquid is refluxed to a liquid phase in the reactor; and the gaseous phase part is only cooled after starting decreasing the temperature of the reaction system, whereby high molecular weight polyarylene sulfide suitable for powder coating is formed, which has a weight average molecular weight of at least 30,000 and an average particle size of 50 to 80 .mu.m, wherein particles of 40 to 150 .mu.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: December 12, 1995
    Assignee: Tonen Chemical Corporation
    Inventors: Yoichi Imai, Osamu Komiyama, Kazuhiro Ichikawa
  • Patent number: 5440009
    Abstract: A method for recovering cyclic oligomers from a poly(arylene sulfide) polymer or poly(arylene sulfide) polymerization reaction mixture is provided in which the cyclic oligomers are maintained in a solution comprising a suitable solvent and the cyclic oligomers; then the solution is contacted with water to cause the formation of a suspension; then the suspension is acidified to cause the flocculation of cyclic oligomers which can then be more easily recovered.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: August 8, 1995
    Assignee: Phillips Petroleum Company
    Inventors: Carlton E. Ash, William A. St. Laurent
  • Patent number: 5438115
    Abstract: A process is provided for producing a poly(arylene sulfide) polymer which employs at least one base as a reactant, wherein the base is contacted with the polymerization reaction mixture incrementally during the polymerization.
    Type: Grant
    Filed: November 30, 1993
    Date of Patent: August 1, 1995
    Assignee: Phillips Petroleum Company
    Inventors: Darryl R. Fahey, Owen H. Decker, Carlton E. Ash, Jon F. Geibel, Fernando C. Vidaurri, Jr., Lacey E. Scoggins, Harvey D. Hensley, Wei-Teh W. Shang, Jimmie J. Straw, Paul J. DesLauriers
  • Patent number: 5424390
    Abstract: A process of producing an aqueous solution of a sulfonated melamine-formaldehyde resin. The process comprises condensing melamine and formaldehyde or a precursor of formaldehyde (e.g. paraformaldehyde) in an aqueous mixture having a pH in the range of 8-10 to form a reaction mixture containing a condensation product of melamine and formaldehyde. The condensation product is then reacted in an aqueous mixture having a pH of 8-10, preferably 8-9, with a sulfonating agent to produce a mixture containing a sulfonated condensation product. Finally, polymerizing the said sulfonated condensation product in an aqueous mixture having a pH of 5-7 to form a resin solution. In the process, at least one of the sulfonation step and the polymerizing step is carried out under superatmospheric pressure (generally 5 to 70 p.s.i.) and at an elevated temperature of, in the case of the sulfonating step, 100.degree.-130.degree. C. for a time of 1 to 5 hours or of, in the case of the polymerizing step, 105-150.degree. C.
    Type: Grant
    Filed: May 17, 1993
    Date of Patent: June 13, 1995
    Assignee: Handy Chemicals Limited
    Inventors: Mario Dupuis, Ioan Spiratos
  • Patent number: 5411776
    Abstract: A sealant comprising a mercapto-terminal liquid oligomer containing plasticizers, fillers and additives wherein the improvement comprises as curing agent an acrylic or methacrylic compound with at least two acrylic or methacrylic groups per molecule and a guanidine derivative as a curing catalyst having good chemical and weathering stability, low water vapor permeability and long-term elasticity properties.
    Type: Grant
    Filed: March 25, 1994
    Date of Patent: May 2, 1995
    Assignee: Morton International, Inc.
    Inventors: Gerald Schmidt, Rainer Jung
  • Patent number: 5405695
    Abstract: Disclosed herein are poly(phenylene sulfide) fibers having a tensile strength of at least 3.5 g/d, a knot tenacity of at least 2 g/d, a loop tenacity of at least 3.5 g/d, the number of abrasion cycles until breaking in a flexing abrasion test of at least 3,000 times, and the number of repeated flexings until breaking in a flexural fatigue test of at least 150 times. A process for the production of poly(phenylene sulfide) fibers, which comprises melt-spinning a poly(phenylene sulfide), stretching the resultant unstretched filaments at a draw ratio of 2:1 to 7:1 within a temperature range of 80.degree.-260.degree. C., and heat-treating the stretched filaments for 0.1-30 seconds under conditions of a take-up ratio of 0.8:1 to 1.35:1 in a dry heat atmosphere exceeding 285.degree. C., but not exceeding 385.degree. C. is also disclosed.
    Type: Grant
    Filed: October 20, 1992
    Date of Patent: April 11, 1995
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Masamichi Akatsu, Eisho Nakano, Hiroyuki Endo, Keiji Sonoda
  • Patent number: 5393861
    Abstract: The polysulfide polyether of the present invention has in a main chain (i) a polyether moiety represented by --(R.sub.1 O)--.sub.n ; (ii) structural units represented by--(C.sub.2 H.sub.4 O CH.sub.2 O C.sub.2 H.sub.4 --S.sub.x)--, and--(CH.sub.2 CH (OH) CH.sub.2 --S.sub.x --);and at both ends (iii) a thiol group represented by--C.sub.2 H.sub.4 O CH.sub.2 O C.sub.2 H.sub.4 --SH, and/or--CH.sub.2 CH (OH) CH.sub.2 --SH.When mixed with epoxy resins, etc., this polymer is cured at a controlled speed.
    Type: Grant
    Filed: April 11, 1994
    Date of Patent: February 28, 1995
    Assignee: Toray Thiokol Co., Ltd.
    Inventors: Kazuhisa Sakae, Kouki Echigoya, Mitsuhiro Okajima
  • Patent number: 5393865
    Abstract: A method is provided for forming poly(arylene sulfide) fibrids by flashing a solution which is comprised of a poly(arylene sulfide) polymer in a polar organic compound and which is essentially free of solids under suitable conditions to form a solidified product comprising poly(arylene sulfide) fibrids.
    Type: Grant
    Filed: September 17, 1993
    Date of Patent: February 28, 1995
    Assignee: Phillips Petroleum Company
    Inventors: Carlton E. Ash, Harold D. Yelton, Owen H. Decker, Jon F. Geibel