Inorganic Sulfur Reactant Contains At Least One Metal Atom Or Contains An Ammonium Ion Patents (Class 528/388)
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Patent number: 5484876Abstract: 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: GrantFiled: July 29, 1994Date of Patent: January 16, 1996Assignee: Kureha Kagaku Kogyo K.K.Inventors: Yukichira Kawakami, Zenya Shiiki
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Process for controlling a particle size of polyarylene sulfide and polyarylene sulfide thus produced
Patent number: 5475081Abstract: 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: GrantFiled: November 12, 1993Date of Patent: December 12, 1995Assignee: Tonen Chemical CorporationInventors: Yoichi Imai, Osamu Komiyama, Kazuhiro Ichikawa -
Patent number: 5440009Abstract: 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: GrantFiled: December 30, 1993Date of Patent: August 8, 1995Assignee: Phillips Petroleum CompanyInventors: Carlton E. Ash, William A. St. Laurent
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Patent number: 5438115Abstract: 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: GrantFiled: November 30, 1993Date of Patent: August 1, 1995Assignee: Phillips Petroleum CompanyInventors: 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
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Patent number: 5424390Abstract: 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: GrantFiled: May 17, 1993Date of Patent: June 13, 1995Assignee: Handy Chemicals LimitedInventors: Mario Dupuis, Ioan Spiratos
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Patent number: 5411776Abstract: 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: GrantFiled: March 25, 1994Date of Patent: May 2, 1995Assignee: Morton International, Inc.Inventors: Gerald Schmidt, Rainer Jung
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Patent number: 5405695Abstract: 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: GrantFiled: October 20, 1992Date of Patent: April 11, 1995Assignee: Kureha Kagaku Kogyo K.K.Inventors: Masamichi Akatsu, Eisho Nakano, Hiroyuki Endo, Keiji Sonoda
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Patent number: 5393861Abstract: 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: GrantFiled: April 11, 1994Date of Patent: February 28, 1995Assignee: Toray Thiokol Co., Ltd.Inventors: Kazuhisa Sakae, Kouki Echigoya, Mitsuhiro Okajima
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Patent number: 5393865Abstract: 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: GrantFiled: September 17, 1993Date of Patent: February 28, 1995Assignee: Phillips Petroleum CompanyInventors: Carlton E. Ash, Harold D. Yelton, Owen H. Decker, Jon F. Geibel
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Patent number: 5391645Abstract: Disclosed herein are a poly(arylene thioether-ketone) copolymer comprising (A) at least one poly(arylene thioether-ketone) segment having predominant recurring units of the formula ##STR1## wherein the --CO-- and --S-- are in the para position to each other, and (B) at least one poly(arylene thioether) segment having predominant recurring units of the formula ##STR2## (a) the ratio of the total amount of the poly(arylene thioether) segment (B) to the total amount of the poly(arylene thioether-ketone) segment (A) ranging from 0.05 to 5 by weight, (b) the number-average polymerization degree of the poly(arylene thioether) segment (B) being higher than 1 but lower than 10, and (c) said copolymer having a melt viscosity of 2-100,000 poises as measured at 350.degree. C. and a shear rate of 1,200/sec as well as a production process of the poly(arylene thioether-ketone) copolymer.Type: GrantFiled: May 20, 1993Date of Patent: February 21, 1995Assignee: Kureha Kagaku Kogyo K.K.Inventors: Yoshikatsu Satake, Yoshiyuki Inaguma, Yasuhiro Suzuki
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Patent number: 5391646Abstract: Disclosed herein are a poly(arylene thioether-ketone) copolymer comprising (A) at least one poly(arylene thioether-ketone) segment having predominant recurring units of the formula ##STR1## wherein the --CO-- and --S-- are in the para position to each other and (B) at least one poly(arylene thioether) segment having predominant recurring units of the formula ##STR2## (a) the ratio of the total amount of the poly(arylene thioether) segment (B) to the total amount of the poly(arylene thioether-ketone) segment (A) ranging from 0.05 to 5 by weight, (b) the number-average polymerization degree of the poly(arylene thioether) segment (B) being higher than 1 but lower than 10, and (c) said copolymer having a melt viscosity of 2-100,000 poises as measured at 350.degree. C. and a shear rate of 1,200/sec as well as a production process of the poly(arylene thioether-ketone) copolymer.Type: GrantFiled: May 20, 1993Date of Patent: February 21, 1995Assignee: Kureha Kagaku Kogyo K.K.Inventors: Yoshikatsu Satake, Yoshiyuki Inaguma, Yasuhiro Suzuki
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Patent number: 5384391Abstract: A process for preparing polyarylene sulfides which comprises providing at least one cyclic arylene sulfide oligomer of the formula ##STR1## wherein S represents a sulfur atom, groups Ar, which may be the same or different, represent each an arylene radical having 6-24 carbon atoms, groups R, which may be the same or different, represent each a C.sub.1 -C.sub.12 alkyl radical, or a C.sub.1 -C.sub.12 alkoxy radical, or a primary or secondary amino group, n is an integer of from 2 to 50, and m is an integer of from 0 to 15, and heating said cyclic oligomer I in the presence of a ring opening polymerization catalyst so as to form polyarylene sulfide. The process produces polyarylene sulfides improved in chemical, physical and mechanical properties.Type: GrantFiled: December 27, 1993Date of Patent: January 24, 1995Assignee: Tosoh CorporationInventors: Hiroshi Miyata, Hiroshi Inoue, Akira Akimoto
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Patent number: 5380821Abstract: Process for the manufacture of poly(arylene sulphide) comprising the reaction of a dihalogenated aromatic compound with alkali metal sulphide in a polar organic solvent in the presence of a compound chosen from sulphimides and their alkali metal salts.Type: GrantFiled: June 14, 1993Date of Patent: January 10, 1995Assignee: Solvay (Societe Anonyme)Inventors: Pierre Dournel, Danny Van Hoyweghen, Ardechir Momtaz
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Patent number: 5374709Abstract: A method for removing oligomers and non-polymeric impurities from poly(arylene sulfide) polymers and producing the polymers in easily recoverable granular form is provided in which a poly(arylene sulfide) polymer associated with oligomers and non-polymeric impurities is contacted with a solvent, water, and optionally, a base, at a sufficient temperature to substantially dissolve the polymer, oligomers and impurities; then the solution is cooled to a temperature at which the poly(arylene sulfide) precipitates while oligomers and impurities remain in solution, then the precipitated polymer is separated from the solution containing the oligomers and impurities. A polymer product produced by this method is also disclosed.Type: GrantFiled: October 23, 1992Date of Patent: December 20, 1994Assignee: Phillips Petroleum CompanyInventors: Earl Clark, Jr., Lacey E. Scoggins, Glenn F. Kile
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Patent number: 5367049Abstract: Process for the manufacture of poly(arylene sulphide) consisting in polymerizing, in one stage, a reaction mixture comprising the following constituents:an alkali metal sulphide (a);a polar organic solvent (b);an alkali metal carboxylate (c);water (d);a dihalogenated aromatic compound (e); characterized by the combination, in the said mixture, of a molar ratio (R.sub.H.sbsb.2.sub.O) of the water (d) to the sulphide (a) used such that:2.6.ltoreq.R.sub.H.sbsb.2.sub.O .ltoreq.3.8and of a molar ratio (R.sub.ADD) of the carboxylate (c) to the sulphide (a) used such that:0.20.ltoreq.R.sub.ADD .ltoreq.0.Type: GrantFiled: August 16, 1993Date of Patent: November 22, 1994Assignee: Solvay (Societe Anonyme)Inventors: Danny Van Hoyweghen, Jean-Marc Coisne
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Patent number: 5364928Abstract: A process for preparing high molecular weight arylene sulfide polymers by dehydrating an aqueous mixture of a sulfur source and a cyclic organic amide to form a dehydrated mixture, contacting the dehydrated mixture with a dihaloaromatic compound to produce a polymerization mixture, polymerizing the polymerization mixture and recovering the arylene sulfide polymer wherein an aqueous alkali metal carboxylate mixture is added to the polymerization mixture after the conversion of the dihaloaromatic compound is about 40 percent to about 30 minutes prior to entering into termination of the polymerization.Type: GrantFiled: May 14, 1993Date of Patent: November 15, 1994Assignee: Phillips Petroleum CompanyInventor: Carlton E. Ash
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Patent number: 5360890Abstract: Fractional refining of crude polyarylene sulfides as synthesized provide refined polyarylene sulfides exhibiting improved mechanical properties. A reaction mixture liquor comprising a crude product polyarylene sulfide in an organic amide medium is subjected to distillation for removal of the amide medium. Then the residue is leached with a hot solvent so as to recover a higher molecular weight fraction (solid) and discard a lower molecular weight fraction (liquid).Type: GrantFiled: December 22, 1993Date of Patent: November 1, 1994Assignee: Tosoh CorporationInventors: Shinji Tanaka, Hiroshi Inoue
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Patent number: 5354841Abstract: A process is provided for producing a poly(arylene sulfide) polymer which employs as a reactant cyclic arylene sulfide oligomers.Type: GrantFiled: August 9, 1993Date of Patent: October 11, 1994Assignee: Phillips Petroleum CompanyInventors: Jon F. Geibel, Carlton E. Ash
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Patent number: 5352768Abstract: A method is provided for producing a poly(arylene sulfide) polymer having reduced amounts of impurities by contacting a poly(arylene sulfide) polymerization reaction mixture with an acid.Type: GrantFiled: October 23, 1992Date of Patent: October 4, 1994Assignee: Phillips Petroleum CompanyInventors: John D. Stuber, Wei-Teh W. Shang, Lacey E. Scoggins
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Patent number: 5350833Abstract: In a process for preparing a polyarylene sulfide by reacting an alkali metal sulfide and at least one dihaloaromatic compound in an organic amide solvent at an elevated temperature: a highly pure anhydrous alkali metal sulfide reactant having a purity of at least 95% by weight and a content of alkali metal hydrosulfide impurity of not greater than 2% by weight is employed. The water is deliberately added in a proportion of 0.1 to 0.8 moles per each mole of the alkali metal sulfide used in the process. The alkali metal sulfide reactant is charged in a concentration of 2.5 to 5 moles per liter of the reaction mixture. The deliberate addition of water enables one to omit a dehydration stage which has been desirably or rather necessarily effected to obtain a satisfactory polymer product where a hydrous alkali metal sulfide reactant is employed.Type: GrantFiled: June 25, 1993Date of Patent: September 27, 1994Assignee: Tosoh CorporationInventors: Hiroshi Inoue, Toshikazu Kato
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Patent number: 5350834Abstract: Poly(arylene sulfide/sulfone) polymers are treated in order to increase melt stability and decrease impurities by contacting the poly(arylene sulfide/sulfone) polymer with a soluble zinc compound and an acidic solution. In one embodiment, the polymer is treated first with the soluble zinc compound, followed by treatment with the acidic solution. In another embodiment, the polymer is treated in one step with a solution comprising a water soluble zinc compound in an acidic solution.Type: GrantFiled: May 14, 1993Date of Patent: September 27, 1994Assignee: Phillips Petroleum CompanyInventors: Rex L. Bobsein, Michael C. Yu, Roy F. Wright, David A. Soules
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Patent number: 5342920Abstract: High molecular weight polyarylene sulfide prepared by reacting an alkali metal sulfide with a dihaloaromatic compound in an organic amide solvent, wherein a gaseous phase part of a reactor is cooled 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. Higher molecular weight is attained by copolymerization with 0.005 to 1.5 mole percent, based on the alkali metal sulfide, of a polyhaloaromatic compound.Type: GrantFiled: December 16, 1992Date of Patent: August 30, 1994Assignee: Tonen Chemical CorporationInventors: Yoichi Imai, Toshiyuki Hirano, Osamu Komiyama, Hidenori Yamanaka
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Patent number: 5334701Abstract: A method is provided for selectively extracting the lower molecular weight fraction of a poly(arylene sulfide) polymer by contacting the polymer with a polar organic compound and a promoter compound to form a less dense polymer-lean liquid phase and a more dense polymer-rich liquid phase, separating the polymer-lean liquid phase from the polymer-rich liquid phase, and recovering the polymer from the polymer-rich phase. Alternatively, either of the phases can be isolated and polar organic compound and optionally promoter can be added to form two new phases, followed by isolation of the new polymer-rich phase. This process can be repeated as often as desired or practicable in order to recover polymer having a desired molecular weight and/or molecular weight distribution.Type: GrantFiled: October 23, 1992Date of Patent: August 2, 1994Assignee: Phillips Petroleum CompanyInventors: Carlton E. Ash, Jon F. Geibel, Randy L. Hagenson, David A. Soules
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Patent number: 5331069Abstract: Poly(arylene sulfide sulfone) polymers recovered from a reaction mixture produced by contacting at least one haloaromatic sulfone, at least one sulfur source, and a polar organic compound at polymerization conditions are treated with (1) a haloaromatic sulfone mixture comprising at least one haloaromatic sulfone and a polar organic compound followed by contacting the polymer with (2) a zinc compound. The two-step treatment improves the melt stability and extrudate quality of the polymer.Type: GrantFiled: October 27, 1992Date of Patent: July 19, 1994Assignee: Phillips Petroleum CompanyInventors: Rex L. Bobsein, Earl Clark, Jr.
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Patent number: 5331029Abstract: A resin for bonding polyarylene sulfides is disclosed, comprising a copolymer wherein a main constituent element of the repeating unit of the copolymer is --A--Z--R--Z--, wherein --Z--is an ester linkage; A is an arylene sulfide oligomer component block comprising one or more arylene groups; and R is an organic compound residue formed by removing one atom or one group attached to each of two carbon atoms among carbon atoms constituting either an aliphatic main chain or an aromatic ring and has at most a molecular weight corresponding to an oligomer, but is different from A. An adhesive comprising the resin and a pyrrolidone solvent is also disclosed.Type: GrantFiled: June 14, 1993Date of Patent: July 19, 1994Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Hiroyuki Sato, Kazuhiro Watanabe, Toshiya Watanabe
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Patent number: 5328980Abstract: A process for preparing arylene sulfide polymers is provided, comprising contacting an initiator compound, a halothiophenol compound, an polar organic compound, and a base. Blends comprising the inventive polymers and polyamides or polyaramides provide improved mechanical properties.Type: GrantFiled: December 3, 1992Date of Patent: July 12, 1994Assignee: Phillips Petroleum CompanyInventors: Owen H. Decker, Michael C. Yu
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Patent number: 5326851Abstract: The invention relates to low-viscosity polyarylene sulfides (PAS), preferably polyphenylene sulfides (PPS), which are produced with cycloaliphatic, unsaturated acids as molecular weight regulators.Type: GrantFiled: November 16, 1992Date of Patent: July 5, 1994Assignee: Bayer AGInventors: Burkhard Kohler, Udo Wolf, Wolfgang Russeler, Wilfried Haese
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Patent number: 5324814Abstract: Disclosed herein is a process for the production of an arylene thioether copolymer (C), wherein an alkali metal sulfide is caused to act on a poly(arylene thioether) (A) having predominant recurring units of the formula [I]: ##STR1## wherein R denotes an alkyl group having 1-6 carbon atoms, and 1 stands for 0 or an integer of 1-4, in a water-containing polar organic solvent so as to depolymerize the poly(arylene thioether) (A), thereby preparing a prepolymer (B) having an alkali thiolate group on at least one terminal thereof and the resultant prepolymer (B) is then subjected to a polymerization reaction with at least one dihalogen-substituted aromatic compound.Type: GrantFiled: April 18, 1991Date of Patent: June 28, 1994Assignee: Kureha Kagaku Kogyo K. K.Inventors: Yukichika Kawakami, Mitsuru Hoshino, Yoshikatsu Satake
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Patent number: 5321121Abstract: Poly(biphenylene sulfide/poly(phenylene sulfide) copolymers are produced by contacting a p-dihalobenzene and a bis-p-halobiphenyl under polymerization condiditons. Additionally a poly(biphenylene sulfide)/poly(phenylene sulfide) copolymer/fiber reinforced composite is provided.Type: GrantFiled: November 30, 1992Date of Patent: June 14, 1994Assignee: Phillips Petroleum CompanyInventors: Michael C. Yu, Jimmie J. Straw
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Patent number: 5312880Abstract: Disclosed herein are a process for the preparation of a carboxylated arylene thioether oligomer, in which an alkali metal sulfide is caused to act on a poly(arylene thioether) so as to depolymerize the poly(arylene thioether), thereby preparing an alkali thiolate-containing oligomer, and a carboxylating agent is then caused to act on the alkali thiolate-containing oligomer, thereby forming the carboxylated arylene thioether oligomer, and a process for the production of an arylene thioether copolymer, wherein the carboxylated arylene thioether oligomer alone, which has been obtained in accordance with this preparation process, or a mixture of the carboxylated oligomer in an amount of at least 50 wt. % and another carboxylic compound in an amount less than 50 wt. % is reacted with an alkylenediol or an alkylenediol and a polyester or an alkylene diol and a lactone.Type: GrantFiled: August 30, 1993Date of Patent: May 17, 1994Assignee: Kureha Kagaku Kogyo K.K.Inventors: Hiroyuki Sato, Mitsuru Hoshino, Yukichika Kawakami
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Patent number: 5312894Abstract: A granular, high-melt-stable poly(arylene thioetherketone) has a solution viscosity (.eta..sub.inh) of at least 0.30 dl/g, a retention (400.degree. C./20 min) of melt crystallization enthalpy (.DELTA.Hmc) of at least 60%, a melting point of 340.degree.-360.degree. C., a glass transition temperature of at least 125.degree. C. and an average particle diameter of 0.1-2 mm. A production process of a granular, high-melt-stable poly(arylene thioether-ketone) comprises reacting an alkali metal sulfide and a dihalogenated aromatic compound consisting principally of a 4,4'-dihalobenzophenone in an organic amide solvent containing water. In the first step, (1) the ratio of the amount of the charged dihalogenated aromatic compound to the amount of the charged alkali metal sulfide is controlled to 0.95-1.2 (mole/mole), (2) the ratio of the water content to the amount of the charged organic amide solvent is controlled to 1-15 (mole/kg), and (3) the reaction is conducted for 3-30 hours at 180.degree.-260.degree. C.Type: GrantFiled: April 27, 1993Date of Patent: May 17, 1994Assignee: Kureha Kagaku Kogyo K.K.Inventors: Yukichika Kawakami, Zenya Shiiki
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Patent number: 5306805Abstract: This invention relates to a simplified process for the preparation of polyarylene sulphides with improved product quality from alkali metal sulphides and dihalogenated aromatic compounds, in which the alkali metal sulphides are prepared and reacted in situ.Type: GrantFiled: February 10, 1992Date of Patent: April 26, 1994Assignee: Bayer AGInventors: Wolfgang Arlt, Wolfgang Alewelt, Karl-Heinrich Meyer, Manfred Schmidt, Erhard Tresper, Wolfgang Eisermann
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Patent number: 5304630Abstract: Disclosed herein are a process for the preparation of a carboxylated arylene thioether oligomer, in which an alkali metal sulfide is caused to act on a poly(arylene thioether) so as to depolymerize the poly(arylene thioether), thereby preparing an alkali thiolate-containing oligomer, and a carboxylating agent is then caused to act on the alkali thiolate-containing oligomer, thereby forming the carboxylated arylene thioether oligomer, and a process for the production of an arylene thioether copolymer, wherein the carboxylated arylene thioether oligomer alone, which has been obtained in accordance with this preparation process, or a mixture of the carboxylated oligomer in an amount of at least 50 wt. % and another carboxylic compound in an amount less than 50 wt. % is reacted with an alkylenediol or an alkylenediol and a polyester or an alkylene diol and a lactone.Type: GrantFiled: August 30, 1993Date of Patent: April 19, 1994Assignee: Kureha Kagaku Kogyo K.K.Inventors: Hiroyuki Sato, Mitsuru Hoshino, Yukichika Kawakami
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Patent number: 5304629Abstract: Disclosed herein are a process for the preparation of a carboxylated arylene thioether oligomer, in which an alkali metal sulfide is caused to act on a poly(arylene thioether) so as to depolymerize the poly(arylene thioether), thereby preparing an alkali thiolate-containing oligomer, and a carboxylating agent is then caused to act on the alkali thiolate-containing oligomer, thereby forming the carboxylated arylene thioether oligomer, and a process for the production of an arylene thioether copolymer, wherein the carboxylated arylene thioether oligomer alone, which has been obtained in accordance with this preparation process, or a mixture of the carboxylated oligomer in an amount of at least 50 wt. % and another carboxylic compound in an amount less than 50 wt. % is reacted with an alkylenediol or an alkylenediol and a polyester or an alkylene diol and a lactone.Type: GrantFiled: August 30, 1993Date of Patent: April 19, 1994Assignee: Kureha Kagaku Kogyo K.K.Inventors: Hiroyuki Sato, Mitsuru Hoshino, Yuichika Kawakami
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Patent number: 5298573Abstract: A process is provided for preparing poly(arylene sulfide sulfone)/poly(arylene sulfide ketone) block copolymers comprising: contacting poly(arylene sulfide sulfone) prepolymer, at least one dihalobenzophenone, a sulfur source, and a polar organic compound under polymerization conditions.Type: GrantFiled: November 13, 1992Date of Patent: March 29, 1994Assignee: Phillips Petroleum CompanyInventor: Dwayne R. Senn
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Patent number: 5298574Abstract: A process is provided for preparing poly(arylene sulfide ketone)/poly(arylene sulfide sulfone) block copolymers comprising: contacting poly(arylene sulfide ketone) prepolymer, at least one dihaloaromatic sulfone, a sulfur source, and a polar organic compound under polymerization conditions. The polymers thus produced exhibit crystalline properties and an increased glass transition temperature.Type: GrantFiled: November 13, 1992Date of Patent: March 29, 1994Assignee: Phillips Petroleum CompanyInventor: Dwayne R. Senn
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Patent number: 5296579Abstract: A process for the production of arylene sulfide polymers is provided which comprises subjecting a mixture of at least one first sulfur source, at least one second sulfur source comprised of at least one organic monothiol compound, at least one polyhalo-substituted aromatic compound and at least one polar organic compound to polymerization conditions sufficient to produce the arylene sulfide polymer. The organic monothiol compound can be added at any time prior to substantial completion of polymerization to provide arylene sulfide polymers of increased extrusion rate.Type: GrantFiled: February 11, 1988Date of Patent: March 22, 1994Assignee: Phillips Petroleum CompanyInventors: Jon F. Geibel, Robert W. Campbell, Guy Senatore, Fernando C. Vidaurri, Mark A. Haney
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Patent number: 5288848Abstract: The invention relates to a process for the preparation of optionally branched, high molecular weight polyarylene sulphides with melt viscosities which can be established at defined values and low corrosion.These polyarylene sulphides are obtained by reacting alkali metal sulphides, if appropriate mixed with alkali metal bisulphides and reaction accelerators, with dihalogenoaromatics and, if appropriate, polyhalogenoaromatics, with the addition of particular monohalogenoaromatics as chain stoppers.Type: GrantFiled: November 17, 1992Date of Patent: February 22, 1994Assignee: Bayer AktiengesellschaftInventors: Karsten Idel, Wolfgang Ebert, Ludwig Bottenbruch, Dieter Freitag, Rolf-Volker Meyer
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Patent number: 5286817Abstract: A process is provided for preparing poly(arylene sulfide)/poly(arylene sulfide sulfone) block copolymer comprising: contacting poly(arylene sulfide) prepolymer, a dihaloaromatic sulfone, a sulfur source, and a polar organic compound under polymerization conditions, wherein said prepolymer is prepared by contacting a dihaloaromatic compound, a phenolic compound, a polar organic compound, and a sulfur source under polymerization conditions.Type: GrantFiled: March 5, 1993Date of Patent: February 15, 1994Assignee: Phillips Petroleum CompanyInventors: Dwayne R. Senn, Carlton E. Ash
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Patent number: 5286809Abstract: This invention relates to thermoplastic moulding compounds based on polyamides and/or polyesters and special functionally modified polyarylene sulphides and optionally conventional additives and to their preparation and their use.Type: GrantFiled: December 9, 1991Date of Patent: February 15, 1994Assignee: Bayer AGInventors: Hans-Detlef Heinz, Burkhard Kohler
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Patent number: 5280104Abstract: A process for preparing poly(arylene sulfide) with reduced metal contamination is produced by contacting a dihaloaromatic compound, a sulfur source, a polar organic compound, and an alkali metal carboxylate in a reaction vessel wherein at least the liquid contacting parts of the vessel are constructed of titanium. In another aspect of the invention a polymer produced by the above described process is provided.Type: GrantFiled: June 30, 1992Date of Patent: January 18, 1994Assignee: Phillips Petroleum CompanyInventors: Jon F. Geibel, Harold D. Yelton
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Patent number: 5278283Abstract: Disclosed is a process for preparing a polyarylene sulfide, which involves polycondensing a dihalogenated aromatic compound with a source of sulfur in an organic polar solvent while dehydrating at pressure under which polycondensation is performed. This process avoids dehydration operation of the raw materials, particularly the source of sulfur, prior to polycondensation, thereby resulting in the production of the polyarylene sulfide having a high molecular weight.Type: GrantFiled: January 13, 1992Date of Patent: January 11, 1994Assignee: Idemitsu Petrochemical Company, LimitedInventors: Akira Miyoshi, Minoru Senga
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Patent number: 5278261Abstract: Low temperature heat curable arylene sulfide copolymer compositions which are particularly suitable for use in coating applications are provided. The compositions basically comprise a first arylene sulfide copolymer having unsubstituted para- and ortho-aromatic sulfide repeating units in the polymer chain, and a second arylene sulfide copolymer having unsubstituted para-aromatic sulfide repeating units and alkyl-substituted aromatic sulfide repeating units in the polymer chain.Type: GrantFiled: December 8, 1992Date of Patent: January 11, 1994Assignee: Phillips Petroleum CompanyInventors: Roy F. Wright, Michael C. Yu
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Patent number: 5274015Abstract: A composition that, when present in a polymer matrix, reduces the deleterious effect of UV light absorption by the polymer is provided, which comprises a sulfur-containing derivative of hydroxyphenylbenzotriazole having the formula of: ##STR1## wherein each X is selected from the group consisting of hydrogen, halogens, cyano, alkyl, phenyl group, biphenyl group, arylthio, amine, ketone, aldehyde, alkoxy, hydroxy, carboxylic acid group, oligomer and combinations thereof and can have carbon atoms up to about 20; n is a whole number from 1 to 5; n' is a whole number from 0 to 4; n" is a whole number from 1 to 2 and each n" can be the same or different; q is an integer from 1 to 10; each Y is selected from the group consisting of --S(O)(O)--, --S(O)--, and --S--; each R can be selected from the group consisting of hydrogen, alkyl group, alkenyl group, aralkyl group, alkaryl group, and combinations thereof and can have 0 to about 10 carbon atoms; each OH group can be at either the 2'- or the 6'-position, or both.Type: GrantFiled: November 24, 1992Date of Patent: December 28, 1993Assignee: Phillips Petroleum CompanyInventors: Paul J. Deslauriers, Darryl R. Fahey, Paritosh K. Das
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Patent number: 5268449Abstract: A random copolymer composed of at least one arylene sulfide segment and at least one arylene aulfide sulfone segment is prepared by contacting at least one dihaloaromatic sulfide having a formula of X--Ar(R).sub.n --S--Ar.sup.1 (R.sup.1).sub.n --X.sup.1, with a mixture comprising at least one sulfur source and at least one dihaloaromatic sulfone having a formula of X.sup.2 --Ar.sup.2 (R.sup.2).sub.n --S(O.sub.2)--Ar.sup.3 (R.sup.3).sub.n --X.sup.3 in the presence of a polar organic compound under polymerization conditions to synthesize a random copolymer; where X, X.sup.1, X.sup.2, and X.sup.3 can be the same or different halogens and are each selected from the group consisting of fluorine, chlorine, bromine and iodine; Ar, Ar.sup.1, Ar.sup.2, and Ar.sup.3 are each an arylene group; R, R.sup.1, R.sup.2, and R.sup.Type: GrantFiled: November 16, 1992Date of Patent: December 7, 1993Assignee: Phillips Petroleum CompanyInventors: Dwayne R. Senn, Rex L. Bobstein, Owen H. Decker, Carlton E. Ash, Darryl R. Fahey, Jon F. Geibel
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Patent number: 5268451Abstract: The present invention discloses a process for producing a granular polyarylene sulfide which has a high melt viscosity and a high degree of cross-linkage, becomes gel under melting and is easy to handle in the production and the fabrication thereof.The process disclosed herein comprises (1) a step (A) an initial-stage polymerization step for obtaining a polyarylene sulfide by reacting an alkali metal sulfide, a dihaloaromatic compound and a polyhaloaromatic compound, having three or more halogen substituents in a molecule, in the presence of water in an amount of 0.5 to 2.9 moles per mol of said alkali metal sulfide at a temperature in the range of 180.degree. to 235.degree. C. until the total conversion ratio of said dihalo- and polyhaloaromatic compounds reaches 50 to 98% and the melt viscosity of a polyarylene sulfide obtained at the end of the step becomes 5 to 5,000 poise, measured at 310.degree. C.Type: GrantFiled: December 3, 1992Date of Patent: December 7, 1993Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Yo Iizuka, Toshio Hosokawa, Yoshinobu Itoh, Shinji Yamamoto, Kazuo Kusida, Takayuki Katto
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Patent number: 5268450Abstract: A composition comprising a stabilizer chemically bonded to a polymer matrix, and which reduces the deleterious effect of UV light absorption by the polymer is provided.Type: GrantFiled: November 24, 1992Date of Patent: December 7, 1993Assignee: Phillips Petroleum CompanyInventors: Paul J. DesLauriers, Darryl R. Fahey, Paritosh K. Das
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Patent number: 5266680Abstract: A method is provided for the production of poly(arylene sulfide) compositions comprisinga) contacting under suitable conditions a sulfur source, a dihalogenated aromatic compound and optionally other halogenated aromatic compounds, a polar organic compound, a base, and an alkali metal carboxylate in order to form a substantially liquid mixture comprising poly(arylene sulfide) polymer, polar organic compound and water;b) slowly cooling to form a slurry comprising solid poly(arylene sulfide) particles and liquid comprising the polar organic compound and water and adding an effective amount of at least one extraction agent;c) contacting the poly(arylene sulfide) particles with an aqueous solution containing calcium ions; andd) recovering the poly(arylene sulfide) composition.The poly(arylene sulfide) compositions prepared according to the invention method are especially useful for the preparation of fibers and monofilaments.Type: GrantFiled: June 24, 1992Date of Patent: November 30, 1993Assignee: Phillips Petroleum CompanyInventor: Jerry O. Reed
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Patent number: 5264515Abstract: A moisture curable composition comprised of a moisture curable base and a curing agent which does not contain molecular water but which produces water upon activation so as to cure the curable base. The composition exhibits improved stability and shelf life and can be formulated so that curing of the composition can be controlled substantially independently of ambient conditions.Type: GrantFiled: December 23, 1991Date of Patent: November 23, 1993Assignee: Rheox, Inc.Inventors: Charles A. Cody, Terrence L. Hartman
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Patent number: 5262517Abstract: Disclosed herein are a process for the preparation of a carboxylated arylene thioether oligomer, in which an alkali metal sulfide is caused to act on a poly(arylene thioether) so as to depolymerize the poly(arylene thioether), thereby preparing an alkali thiolate-containing oligomer, and a carboxylating agent is then caused to act on the alkali thiolate-containing oligomer, thereby forming the carboxylated arylene thioether oligomer, and a process for the production of an arylene thioether copolymer, wherein the carboxylated arylene thioether oligomer alone, which has been obtained in accordance with this preparation process, or a mixture of the carboxylated oligomer in an amount of at least 50 wt. % and another carboxylic compound in an amount less than 50 wt. % is reacted with an alkylenediol or an alkylenediol and a polyester or an alkylene diol and a lactone.Type: GrantFiled: March 27, 1992Date of Patent: November 16, 1993Assignee: Kureha Kagaku Kogyo K.K.Inventors: Hiroyuki Sato, Mitsuru Hoshino, Yukichika Kawakami