Inorganic Sulfur Reactant Contains At Least One Metal Atom Or Contains An Ammonium Ion Patents (Class 528/388)
  • Patent number: 4501902
    Abstract: A process for removing compounds from aprotic solvents in which aprotic solvent containing at least one acidic compound is contacted with a solid inorganic compound chosen from alkaline earth carbonates, alkaline earth hydroxides, alkaline earth oxides, and alumina in which the contact of the solvent with a solid inorganic compound is by the process of fluidized bed contact, stirred slurry contact or trickle bed contact. Contaminated NMP from poly(phenylene sulfide) production is substantially freed of acidic contaminants by a series of fractionations with a treatment of the kettle liquid of at least one fractionation by the method described above and/or a treatment of the overhead of the last fractionation in series by the method described above.
    Type: Grant
    Filed: December 21, 1982
    Date of Patent: February 26, 1985
    Assignee: Phillips Petroleum Company
    Inventor: James W. Cleary
  • Patent number: 4501713
    Abstract: A method for stabilizing the Tmc of PPS subjected to heat treatment in a temperature range between 240.degree. C. and 320.degree. C., particularly during the heating process of an extrusion operation, by increasing the tmperature of the polymer through the 240.degree. C.-320.degree. C. range at a rate of at least 20.degree. C. per minute or by subsequently raising the temperature of the polymer to at least 350.degree. C. for a time sufficient to stabilize the Tmc of the polymer.
    Type: Grant
    Filed: June 15, 1983
    Date of Patent: February 26, 1985
    Assignee: Phillips Petroleum Company
    Inventor: Roy F. Wright
  • Patent number: 4500702
    Abstract: This invention relates to a process for the production of high molecular weight, optionally branched polyarylene sulphides. These polyarylene sulphides may be produced in a polar organic solvent in the absence of water in a one-vessel reaction.
    Type: Grant
    Filed: November 14, 1983
    Date of Patent: February 19, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Edgar Ostlinning, Karsten Idel
  • Patent number: 4495332
    Abstract: A process for obtaining aromatic sulfide polymer which has a markedly high molecular weight and can be readily formed into films, fibers, and other structures. The process comprises heating, in an aprotic solvent to a temperature of 100.degree. to 250.degree. C., (i) a dihaloaromatic compound and (ii) substantially anhydrous fine powder of the sulfide of an alkali or alkaline earth metal in the presence of (iii) substantially anhydrous fine powder of the carbonate of an alkali or alkaline earth metal, or of a mixture thereof with a hygroscopic inorganic salt and (iv) a strictly controlled very small amount of water dissolved in or solvated with the solvent.
    Type: Grant
    Filed: July 27, 1983
    Date of Patent: January 22, 1985
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Zenya Shiiki, Yo Iizuka, Yukichika Kawakami
  • Patent number: 4493927
    Abstract: Condensation polymers having sulfur containing backbones exhibit high char formation properties. Polymers are prepared, for example, by reacting sodium tetrasulfide and dicyclopentadiene dichloroacetate under polymerization conditions.
    Type: Grant
    Filed: December 22, 1983
    Date of Patent: January 15, 1985
    Assignee: The Dow Chemical Company
    Inventors: Kathleen M. McCreedy, Kenneth R. Hilton
  • Patent number: 4490522
    Abstract: A process for production of polyphenylene sulfide which comprises reacting an alkali metal sulfide compound with a polyhalogenated aromatic compound in an organic polar solvent in the presence of an oxyalkylene compound.
    Type: Grant
    Filed: August 2, 1983
    Date of Patent: December 25, 1984
    Assignee: Dainippon Ink & Chemicals, Inc.
    Inventors: Juheiji Kawabata, Toshio Inoue, Toshinori Sugie, Fumihiro Kobata
  • Patent number: 4486578
    Abstract: A stabilized polyphenylene sulfide is provided which comprises a recurring unit ##STR1## wherein the average n between foreign units is greater than about 5, and about 0.05 to 10 mole % per phenylene sulfide unit of an aromatic constituent chemically bonded with said polyphenylene sulfide chain, said aromatic constituent containing an electron attractive group selected from the group consisting of --SO.sub.2 --, --CO--, --NO.sub.2, --SO.sub.3 R, --COOR, wherein R is H, lower aliphatic hydrocarbon groups, aromatic hydrocarbon groups or alkaline metals, and --CONH--, and said stabilized polyphenylene sulfide has a melting point in the range of about 250.degree. C. to about 350.degree. C. Also provided is a method for preparing stabilized polyphenylene sulfide comprising preparing a polyphenylene sulfide consisting mainly of a recurring unit ##STR2## wherein the degree of polymerization of said recurring unit is greater than about 20, and reacting said polyphenylene sulfide with about 0.
    Type: Grant
    Filed: July 1, 1983
    Date of Patent: December 4, 1984
    Assignee: Toray Industries, Inc.
    Inventors: Toshiyuki Asakura, Hiroaki Kobayashi, Yukio Noguchi
  • Patent number: 4482683
    Abstract: Sulfur-containing polymers, such as polyphenylene sulfide are stabilized from releasing sulfur-containing exhaust gases by adding an additive polymer having at least one reactive radical selected from the group consisting of amino radicals, amido radicals, imido radicals, and keto radicals therein, and which is of approximate the same thermal stability as the sulfur-containing polymer, to such sulfur-containing polymer. In other embodiments of the invention, sulfur-stabilization is also achieved by incorporating suitable fundamental building blocks of the additive polymer into the sulfur-containing polymer chain in the form of reactive monomers. Further, in other embodiments, additive polymers or oligomers (so-called telecheles) having reactive radicals at their ends can be introduced into the sulfur-containing polymer chain as copolymers.
    Type: Grant
    Filed: December 1, 1983
    Date of Patent: November 13, 1984
    Assignee: Siemens Aktiengesellschaft
    Inventors: Ferdinand Quella, Hans-Friedrich Schmidt
  • Patent number: 4478969
    Abstract: The heat stability of arylene sulfide resins, such as poly(p-phenylene sulfide) resin, is improved by the addition of cure retarders comprising an aminotriazole. The resin compositions of the invention are particularly applicable for reducing gel formation during melt extrusion.
    Type: Grant
    Filed: June 22, 1983
    Date of Patent: October 23, 1984
    Assignee: Phillips Petroleum Company
    Inventors: Jerry O. Reed, Ronald D. Mathis
  • Patent number: 4476284
    Abstract: Poly(arylene sulfide) compositions and process comprising producing poly(arylene sulfide) in the presence of a thermoplastic elastomeric hydrogenated conjugated diene/monovinyl arene block copolymer present in an amount sufficient to improve the physical properties of the composition.
    Type: Grant
    Filed: May 20, 1983
    Date of Patent: October 9, 1984
    Assignee: Phillips Petroleum Company
    Inventor: James W. Cleary
  • Patent number: 4464507
    Abstract: The invention describes a process for the preparation of optionally branched polyarylene sulphides in organophosphorus compounds as solvents.
    Type: Grant
    Filed: April 11, 1983
    Date of Patent: August 7, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Edgar Ostlinning, Karsten Idel
  • Patent number: 4454189
    Abstract: This invention relates to a sheet which is formed by randomly dispersing and accumulating polyphenylene sulfide (PPS) filaments and to a process for producing the same. The filaments drawn by a high-velocity air stream are formed directly into a sheet. The sheet is useful as industrial filters, heat insulating materials, electrical insulating materials, etc. because of its outstanding chemical resistance, heat resistance, and electrical insulating properties.
    Type: Grant
    Filed: February 8, 1982
    Date of Patent: June 12, 1984
    Assignee: Toray Industries, Inc.
    Inventor: Shunsuke Fukata
  • Patent number: 4451644
    Abstract: The invention relates to a process for the preparation of polyarylene sulphides in alkylated polyureas at a temperature of 250.degree. to 290.degree. C. under a pressure from 4 to 50 bars.
    Type: Grant
    Filed: February 8, 1983
    Date of Patent: May 29, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Edgar Ostlinning, Karsten Idel, Otto Neuner, Ludwig Bottenbruch
  • Patent number: 4451640
    Abstract: Disclosed herein is a process for producing an aromatic sulfide polymer, comprising the step of reacting elementary sulfur, a polyhalogen-substituted aromatic compound, an aldehyde or a condensate thereof and a caustic alkali in an organic solvent.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: May 29, 1984
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Zenya Shiiki, Yukichika Kawakami
  • Patent number: 4447597
    Abstract: A method for adjusting the cure rate of a mixture of arylene sulfide polymer particles in which the particles of an arylene sulfide polymer mixture are classified by size groups, the size groups of classified particles are segregated, and at least one size group is removed from the mixture. In a further embodiment at least one size group of classified particles removed from one mixture is added to another mixture of polymer particles. In another embodiment the further use of the segregated size groups of classified particles is based upon a determination of the cure rate of at least one segregated size group of particles.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: May 8, 1984
    Assignee: Phillips Petroleum Company
    Inventors: Ronald D. Mathis, Jerry A. Reed
  • Patent number: 4440915
    Abstract: A stabilized polyphenylene sulfide is provided which comprises a recurring unit ##STR1## wherein the average n between foreign units is greater than about 5, and about 0.05 to about 10 mole % per phenylene sulfide unit of an aromatic constituent chemically bonded with said polyphenylene sulfide chain, said aromatic constituent containing an electron attractive group selected from the group consisting of --SO.sub.2 --, --CO--, --NO.sub.2, --SO.sub.3 R, --COOR, wherein R is H, lower aliphatic hydrocarbon groups, aromatic hydrocarbon groups or alkaline metals, and --CONH--, and said stabilized polyphenylene sulfide has a melting point in the range of about 250.degree. C. to about 350.degree. C. Also provided is a method for preparing stabilized polyphenylene sulfide comprising preparing a polyphenylene sulfide consisting mainly of a recurring unit ##STR2## wherein the degree of polymerization of said recurring unit is greater than about 20, and reacting said polyphenylene sulfide with about 0.
    Type: Grant
    Filed: November 22, 1982
    Date of Patent: April 3, 1984
    Assignee: Toray Industries, Inc.
    Inventors: Toshiyuki Asakura, Hiroaki Kobayashi, Yukio Noguchi
  • Patent number: 4438259
    Abstract: Di(vinylaryl)alkyl polysulfides and curable, low odor (vinylaryl)alkyl-terminated polysulfide copolymers having the general structure ##STR1## wherein n is an integer from about 2 to about 8, 1 and m are positive integers, each R is independently an organic polyradical with the radicals residing on carbon atoms, p is zero or a positive integer which is the difference between the number of radicals on R and 2, and each Z is independently chosen from the class consisting of (vinylaryl)alkyl and other noncrosslinking monoradicals, provided that a sufficient proportion of the Z groups are (vinylaryl)alkyl that the polymer, when cured, does not cold flow. Additionally, a method of preparing said polymers and useful adhesive, sealant and caulking compositions made therefrom are disclosed.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: March 20, 1984
    Assignee: The Dow Chemical Company
    Inventors: Victor E. Meyer, Thomas E. Dergazarian
  • Patent number: 4433138
    Abstract: High molecular weight p-polyarylensulfides having a high melt viscosity, capable of being processed thermoplastically, and have good mechanical properties are produced by reacting components (a), (b), and (c) in a polar solvent with a molar ratio of (a):(c) in the range of 0.85:1 to 1.15:1 and a molar ratio of (c): solvent in the range of 1:2 to 1:15, for a time of up to 10 hours at a temperature of from 160.degree. C. to 300.degree. C.
    Type: Grant
    Filed: May 17, 1982
    Date of Patent: February 21, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karsten Idel, Dieter Freitag, Ludwig Bottenbruch, Otto Neuner
  • Patent number: 4424338
    Abstract: Arylene sulfide polymers such as polyphenylene sulfide containing ash-forming impurities or materials verified by contacting an aqueous mixture of such polymer with molecular oxygen and a finite, but small, effective amount of a mineral acid under conditions sufficient to reduce the ash-forming impurities and concurrently at least partially cure the polymer.
    Type: Grant
    Filed: September 10, 1982
    Date of Patent: January 3, 1984
    Assignee: Phillips Petroleum Company
    Inventor: James W. Cleary
  • Patent number: 4424339
    Abstract: Process for preparing polyarylensulfides by reacting dihalogenobenzenes, optionally substituted with polyhalogenoaromatic compounds with 3 or 4 halogeno substituents, and alkali metal sulfide in polar solvents using alkali metal sulfites and/or alkaline earth metal sulfites as catalysts.
    Type: Grant
    Filed: September 13, 1982
    Date of Patent: January 3, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karsten Idel, Edgar Ostlinning, Dieter Freitag, Ludwig Bottenbruch
  • Patent number: 4421910
    Abstract: The curing of arylene sulfide polymers is accelerated by the addition of an effective amount of at least one metal salt of dihydrocarbyldithiophosphinic acid.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: December 20, 1983
    Assignee: Phillips Petroleum Company
    Inventor: Ronald D. Mathis
  • Patent number: 4415729
    Abstract: A method for recovering granular poly(arylene sulfide) from a polymerization reaction mixture at a temperature above that at which poly(arylene sulfide) is in molten phase comprising polar organic solvent and poly(arylene sulfide) in which, in the presence of a sufficient amount of separation agent to cause a phase separation of molten poly(arylene sulfide) and polar organic solvent, the temperature of the polymerization reaction mixture is reduced sufficiently to solidify the poly(arylene sulfide) to produce a slurry comprising particulate poly(arylene sulfide) in polar organic solvent. In a preferred embodiment a slurry comprising particulate poly(phenylene sulfide) in N-methyl-2-pyrrolidone is produced using water, and optionally an alkali metal carboxylate, as separation agent.
    Type: Grant
    Filed: June 4, 1982
    Date of Patent: November 15, 1983
    Assignee: Phillips Petroleum Company
    Inventors: Lacey E. Scoggins, Bradley L. Munro
  • Patent number: 4413083
    Abstract: A composition comprising an intimate mixture of a polyarylene sulphide with an aryl ester of an aryl alcohol. The mixture can be a dry powder mixture, a wet powder mixture, a paste, a suspension a liquid solution or a solid solution. The preferred mixture comprises polyphenylene sulphide and benzyl benzoate. There is also described a method of curing polyphenylene sulphide comprising dissolving the polyphenylene sulphide in benzyl benzoate and heating the solution so that the benzyl benzoate evaporates and the polyphenylene sulphide cures simultaneously.
    Type: Grant
    Filed: March 3, 1982
    Date of Patent: November 1, 1983
    Assignee: The Glacier Metal Company Limited
    Inventor: Glyndwr J. Davies
  • Patent number: 4412062
    Abstract: The addition of cure retarders chosen from among the following classes of compounds: tetraoxaphosphaspiroundecane, 4-hydroxybenzyl isocyanurate, N-hydrocarbylthiophthalimide, and trihydrocarbyl trithiophosphite improves the melt stability and reduces the melt viscosity of arylene sulfide resins, such as poly(phenylene sulfide) resin.
    Type: Grant
    Filed: June 25, 1982
    Date of Patent: October 25, 1983
    Assignee: Phillips Petroleum Company
    Inventor: Jerry O. Reed
  • Patent number: 4405767
    Abstract: Novel poly(arylene sulfide) polymers having enhanced curing properties are produced by treating a poly(phenylene sulfide) polymer (1) at least one alkali metal sulfide; and (2) at least one N-alkyl lactam followed by the addition of (3) at least one polyhaloaromatic compound. The resulting polymers can be fabricated into shaped products having desirable properties.
    Type: Grant
    Filed: June 22, 1982
    Date of Patent: September 20, 1983
    Assignee: Phillips Petroleum Company
    Inventors: William H. Beever, Donnie G. Brady
  • Patent number: 4405745
    Abstract: The heat stability of arylene sulfide polymers, such as poly(p-phenylene sulfide), is improved by the addition of cure retarders comprising alkaline earth metal nitrites.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: September 20, 1983
    Assignee: Phillips Petroleum Company
    Inventors: Ronald D. Mathis, Jerry O. Reed
  • Patent number: 4393197
    Abstract: A method for producing arylene sulfide polymer in which a reaction mixture containing at least one polyhalo-substituted aromatic compound, at least one organic amide, at least one alkali metal carboxylate, H.sub.2 S and water in an amount up to 5 weight percent of the total of the reaction mixture components is contacted at polymerization conditions for a time sufficient to produce polymer. In a preferred embodiment, at least one alkali metal carboxylate is present in the reaction mixture.
    Type: Grant
    Filed: February 16, 1982
    Date of Patent: July 12, 1983
    Assignee: Phillips Petroleum Company
    Inventor: James T. Edmonds, Jr.
  • Patent number: 4383080
    Abstract: A poly(arylene sulfide) polymer is cured in the presence of an ozone containing gas thereby reducing the time required for the curing process.
    Type: Grant
    Filed: April 5, 1982
    Date of Patent: May 10, 1983
    Assignee: Phillips Petroleum Company
    Inventor: Robert L. Dupree
  • Patent number: 4378442
    Abstract: A hardener for a polysulphide sealant comprises an inorganic peroxide and according to the invention includes as a cure control agent a naphthenate e.g. copper naphthenate and/or a phenolic compound e.g. cresylic acid.
    Type: Grant
    Filed: March 17, 1982
    Date of Patent: March 29, 1983
    Inventors: Andrew J. Marsh, Terence F. Watkins
  • Patent number: 4373090
    Abstract: A method for producing arylene sulfide polymer in which an anhydrous reaction mixture containing at least one polyhalo-substituted aromatic compound, at least one organic amide, at least one alkali metal hydroxide, and H.sub.2 S is maintained at polymerization conditions for a time sufficient to produce polymer. In a preferred embodiment the reaction mixture contains at least one alkali metal salt derived from a monocarboxylic acid or carbonic acid.
    Type: Grant
    Filed: February 16, 1982
    Date of Patent: February 8, 1983
    Assignee: Phillips Petroleum Company
    Inventor: James T. Edmonds, Jr.
  • Patent number: 4371671
    Abstract: A method for dehydrating pre-polymerization mixtures in the preparation of poly(arylene sulfide) in which a reaction mixture of a sulfur source and an organic amide are contacted at an essentially constant pressure within a range of about 4 psig to about 40 psig and a first temperature in a range of about 300.degree. F. to 400.degree. F. to form a complex of the reactants with the mixture subsequently maintained at essentially constant pressure while elevating the temperature to a second temperature at which, at the chosen pressure, essentially all water is removed from the mixture. Other compounds including bases, alkali metal carboxylates, alkali metal carbonates, lithium halides, and lithium borate can be present in the reaction mixture. Preferably the sulfur source is sodium sulfide and the organic amide is N-methylpyrrolidone.
    Type: Grant
    Filed: September 1, 1981
    Date of Patent: February 1, 1983
    Assignee: Phillips Petroleum Company
    Inventor: Kenneth L. Anderson
  • Patent number: 4370469
    Abstract: A sheet-like material and a printed circuit board comprised of the sheet-like material with a metallic film laminated thereon are provided wherein the sheet-like material is comprised of a composition mainly consisting of high molecular weight poly p-phenylenesulfide, characterized in that:a. the amount of related materials extracted through chloroform extraction of the poly p-phenylenesulfide containing related materials is less than 1.5 wt % of the entire weight of said poly p-phenylenesulfide prior to said extraction, andb. as measured by wide angle X-ray diffraction,(i) the index of crystallinity of said poly p-phenylenesulfide is in the range of above 2.5 and below 8.0,(ii) the crystallite size of said poly p-phenylenesulfide is in the range of above 50 A and below 100 A, and(iii) the orientation factors of said poly p-phenylenesulfide, measured in three directions comprising through the sample, edgewise and endwise, are above 0.70, as measured by wide angle x-ray diffraction.
    Type: Grant
    Filed: March 10, 1981
    Date of Patent: January 25, 1983
    Assignee: Toray Industries, Inc.
    Inventors: Yukichi Deguchi, Yukio Noguchi, Hiroaki Kobayashi
  • Patent number: 4370470
    Abstract: A contacting apparatus that is a vertically elongated, cylindrical shell having closed ends and separated by horizontal baffle plates into a multiplicity of discrete chambers with access from one chamber to another through concentric circular holes, axially centered in the baffles with a continuously rotatable shaft extending concentric with the baffles within the shell with at least one agitator means attached to the shaft positioned in each chamber and with the shaft in the circular openings providing annular openings in the baffles such the the ratio of backflow rate to feed rate through the openings is less than 1.5.
    Type: Grant
    Filed: April 16, 1981
    Date of Patent: January 25, 1983
    Assignee: Phillips Petroleum Company
    Inventors: Fernando C. Vidaurri, Kenneth L. Anderson
  • Patent number: 4370471
    Abstract: A method for curing particulate arylene sulfide polymer in which the particulate polymer is preheated from ambient temperature to a skin temperature within the range of about 230.degree. to about 260.degree. C. by agitating the particulate polymer in a polisher apparatus, transferring the preheated particles to a curing vessel, and further heating the preheated particulate polymer in the curing vessel for a time and at a temperature to produce cured polymer having a pre-selected melt flow range. Preferably, preheating is carried out continuously with the heated polymer delivered to alternative curing vessels wherein the curing is carried out batch wise.
    Type: Grant
    Filed: May 6, 1981
    Date of Patent: January 25, 1983
    Assignee: Phillips Petroleum Company
    Inventor: Emigdio J. Salmon
  • Patent number: 4368321
    Abstract: A method for dehydrating pre-polymerization mixtures in the preparation of poly(arylene sulfide) in which a reaction mixture of a sulfur source and an organic amide are contacted at a first pressure within a range of about 20 psig to about 60 psig and an initial temperature in a range of about 300.degree. F. to 400.degree. F. to form a complex of the reactants with the mixture subsequently subjected to a decrease in pressure while elevating the temperature to a second temperature at which, at the chosen pressure, essentially all water is removed from the mixture. Other compounds including bases, alkali metal carboxylates, alkali metal carbonates, lithium halides, and lithium borate can be present in the reaction mixture. Preferably the sulfur source is sodium sulfide and the organic amide is N-methylpyrrolidone.
    Type: Grant
    Filed: September 1, 1981
    Date of Patent: January 11, 1983
    Assignee: Phillips Petroleum Company
    Inventors: Fred T. Sherk, Harry B. Hammer
  • Patent number: 4362864
    Abstract: A process for preparing a polyarylene sulphide which comprises reacting(a) dihalogenobenzene consisting of 50 to 100 mol % of a compound of the formula ##STR1## or a compound of the formula ##STR2## or a mixture thereof and of 0 to 50 mol % of a compound of the formula ##STR3## wherein X is halogen and each R is selected from the group consisting of hydrogen, alkyl having 1 to 20 carbon atoms, cycloalkyl having 5 to 20 carbon atoms, aryl having 6 to 24 carbon atoms, alkaryl having 7 to 24 carbon atoms and aralkyl having 7 to 24 carbon atoms with the proviso that at least one R is other than hydrogen and(b) 0 to 3.0 mol % based on the dihalogenobenzene content of a polyhalogeno aromatic of the formulaArX.sub.n (IV)wherein Ar is an aromatic or heterocyclic radical with 6 to 24 carbon atoms having at least 3 free valencies, X is halogen and n is .gtoreq. 3 with(c) an alkyl metal sulphide in(d) a polar solvent in the presence of(e) 0.05-2.
    Type: Grant
    Filed: May 14, 1981
    Date of Patent: December 7, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karsten Idel, Dieter Freitag, Ludwig Bottenbruch, Josef Merten
  • Patent number: 4350810
    Abstract: A process for the production of branched polymers of arylene sulfide in which a reaction mixture of (1) at least one p-dihalobenzene, (2) at least one alkali metal sulfide, (3) at least one organic amide, (4) water in an amount of about 1.0 mole to about 2.4 moles per mole of alkali metal sulfide, and (5) at least one alkali metal carboxylate is contacted under polymerization conditions for a time sufficient to form arylene sulfide polymer and the arylene sulfide polymer formed in said reaction mixture is contacted under polymerization conditions with a polyhaloaromatic compound having more than two halogen substituents per molecule for a time having a range of up to about 75 minutes before entering upon termination of the polymerization process. An embodiment of the process in which the alkali metal sulfide is produced in situ by the reaction of an excess of alkali metal hydroxide with alkali metal hydrosulfide.
    Type: Grant
    Filed: May 8, 1981
    Date of Patent: September 21, 1982
    Assignee: Phillips Petroleum Company
    Inventors: Dale O. Tieszen, Lacey E. Scoggins
  • Patent number: 4346191
    Abstract: An alkali metal hydroxide, sulfur, a polyfunctional amine and an oxidated silicon compound are mixed, then heated to just above the melting temperature of sulfur while agitating for 10 to 30 minutes, thereby producing an alkali metal amine polysulfide silicate reaction product; then it is added to an aqueous solution containing an emulsifying or dispersing agent and is reacted with a polysubstituted organic compound, thereby producing a poly(amine polysulfide silicate) resinous product which may be used to cure epoxy resins.
    Type: Grant
    Filed: March 3, 1981
    Date of Patent: August 24, 1982
    Inventor: David H. Blount
  • Patent number: 4331801
    Abstract: Preparation of a polyarylene sulphide by polycondensing a substituted p-dihalogenobenzene and optionally a polyhalogeno aromatic compound having at least three halo substituents with an alkali metal sulphide in a polar solvent in the presence of a catalytic amount of a di-alkali metal salt of a phosphonic acid.
    Type: Grant
    Filed: July 23, 1980
    Date of Patent: May 25, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karsten Idel, Josef Merten
  • Patent number: 4324886
    Abstract: Alkali metal aminoalkanoate is prepared by contacting in the presence of an alkali metal carboxylate a reaction mixture in which there is at least one alkali metal hydroxide, at least one lactam, and water. Arylene sulfide polymer is prepared by contacting at polymerization conditions a reaction mixture that contains at least one alkali metal aminoalkanoate prepared as described above; at least one polyhalo-substituted aromatic compound; at least one organic amide as solvent and H.sub.2 S. In an embodiment of the polymerization the organic amide used as solvent can be the same as the lactam from which the alkali metal aminoalkanoate was produced.
    Type: Grant
    Filed: May 6, 1980
    Date of Patent: April 13, 1982
    Assignee: Phillips Petroleum Company
    Inventors: James T. Edmonds, Jr., Lacey E. Scoggins
  • Patent number: 4321358
    Abstract: In the pre-curing of particulate poly(arylene sulfide) by contact with an oxygen-containing gas in a vessel at a temperature elevated to a range of about 10.degree. to about 70.degree. C. below the melt point of the resin, upon reaching the desired level of pre-cure, the particulate resin is contacted with water thereby rapidly to reduce the temperature level below the temperature at which curing occurs.
    Type: Grant
    Filed: December 2, 1980
    Date of Patent: March 23, 1982
    Assignee: Phillips Petroleum Company
    Inventor: Robert P. Zelinski
  • Patent number: 4314920
    Abstract: The use of polysulfide rubbers cured with zinc oxide and tetramethylthiuram disulfide and other sulfur containing cure accelerators for polyisoprene rubbers in hot applied processes and articles formed thereby are disclosed. The compositions are useful as hot applied sealants and in the extrusion of hoses and similar rubber articles.
    Type: Grant
    Filed: March 12, 1980
    Date of Patent: February 9, 1982
    Assignee: Thiokol Corporation
    Inventor: Edward G. Millen
  • Patent number: 4315093
    Abstract: A fluorinated phthalonitrile of the general formula: ##STR1## wherein R' is F or CF.sub.3, R is (CF.sub.2).sub.p, m is 1 or 2, n is 1 or , p is an integer from 3 to 30, X is 0, 1, 2, or 3, y is 0, 1, 2, or 3 and z is 0 or 1 is prepared by reacting 4-iodophthalonitrile with the appropriate diiodide in the presence of activated copper in a dipolar aprotic solvent. Heating this phthalonitrile to a temperature from about its melting point to about 285.degree. C. produces a polyphthalocyanine resin. If a salt or metal is added prior to the heating, a metal or salt-coordinated polyphthalocyanine is produced. Polyphthalocyanies are useful in coatings, laminates, filament windings, castings, and structural composites.
    Type: Grant
    Filed: November 9, 1979
    Date of Patent: February 9, 1982
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Teddy M. Keller, James R. Griffith
  • Patent number: 4313870
    Abstract: In a method producing a polycondensate by bulk polycondensation of a monomer (or a reactant mixture) which is a fluid at the polycondensation temperature, an improvement which comprises carrying out the polycondensation until substantially the whole polycondensate becomes a solid polydispersion while continually applying a shearing force sufficient for maintaining the polycondensation system in polydispersed state at a temperature of below the sintering of the produced polycondensate but sufficiently high for allowing the polycondensation to proceed substantially.
    Type: Grant
    Filed: September 5, 1978
    Date of Patent: February 2, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shozaburo Imai, Haruo Suzuki, Kuniaki Asai, Katsuji Ueno
  • Patent number: 4303781
    Abstract: Preparation of a polyarylene sulphide by polycondensing a substituted p-dihalogenobenzene and optionally a polyhalogeno aromatic compound having at least three halo substituents with an alkali metal sulphide in a polar solvent in the presence of a catalytic amount of a tri-alkali metal phosphate.
    Type: Grant
    Filed: July 23, 1980
    Date of Patent: December 1, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karsten Idel, Josef Merten
  • Patent number: 4301274
    Abstract: Aromatic sulfide/sulfone polymers are prepared by initially contacting a dihaloaromatic sulfone, an alkali metal sulfide, an organic amide, and, optionally, an alkali metal carboxylate under polymerization conditions and subsequently at or near completion of the polymerization reaction, adding an end-capping agent comprising additional dihaloaromatic sulfone to the reaction mixture producing a polymer exhibiting improved physical properties including melt flow stability. The resulting polymers have utility as coatings, films, molded objects, filaments, fibers, and the like.
    Type: Grant
    Filed: January 29, 1980
    Date of Patent: November 17, 1981
    Assignee: Phillips Petroleum Company
    Inventor: Robert W. Campbell
  • Patent number: 4299951
    Abstract: The tensile strength of shaped articles made from arylene sulfide/sulfone polymers is increased by treating the article with an organic liquid at an elevated temperature. In one embodiment, the organic liquid comprises at least one of selected hydrocarbons, alcohols, and esters.
    Type: Grant
    Filed: January 29, 1980
    Date of Patent: November 10, 1981
    Assignee: Phillips Petroleum Co.
    Inventor: Robert W. Campbell
  • Patent number: 4286018
    Abstract: A biaxially oriented poly-p-phenylene sulfide film comprising recurring units of the formula ##STR1## a melt viscosity of more than 100 poise and less than 600,000 poise at a shear rate of 200 sec.sup.-1 and at 300.degree. C., and a specific gravity of which is more than 1.330 and less than 1.400. The film has improved mechanical properties, thermal dimensional stability and high temperature durability. Typical applications of the film are as electrical insulation, capacitor, magnetic recording medium, packaging material, and so forth.
    Type: Grant
    Filed: April 23, 1979
    Date of Patent: August 25, 1981
    Assignee: Toray Industries, Incorporated
    Inventors: Toshiyuki Asakura, Yukio Noguchi, Hiroaki Kobayashi
  • Patent number: 4282347
    Abstract: A process for the production of branched polymers of arylene sulfide in which a reaction mixture of (1) at least one p-dihalobenzene, (2) at least one alkali metal sulfide, (3) at least one organic amide, (4) water in an amount of about 1.0 mole to about 2.4 moles per mole of alkali metal sulfide, and (5) at least one alkali metal carboxylate is contacted under polymerization conditions for a time sufficient to form arylene sulfide polymer and the arylene sulfide polymer formed in said reaction mixture is contacted under polymerization conditions with a polyhaloaromatic compound having more than two halogen substituents per molecule for a time having a range of up to about 75 minutes before entering upon termination of the polymerization process. An embodiment of the process in which the alkali metal sulfide is produced in situ by the reaction of an excess of alkali metal hydroxide with alkali metal hydrosulfide.
    Type: Grant
    Filed: August 14, 1979
    Date of Patent: August 4, 1981
    Assignee: Phillips Petroleum Company
    Inventors: Dale O. Tieszen, Lacey E. Scoggins
  • Patent number: 4274993
    Abstract: A moldable polyphenylenesulfide is obtained by a heat-treatment of a partially crosslinked or noncrosslinked polyphenylenesulfide at a temperature of higher than 290.degree. C. in an atmosphere being substantially absence of oxygen.
    Type: Grant
    Filed: May 30, 1979
    Date of Patent: June 23, 1981
    Assignee: Asahi Glass Company, Ltd.
    Inventors: Shigeyuki Narisawa, Hiroshi Yanase, Fukuo Kanno