Inorganic Sulfur Reactant Contains At Least One Metal Atom Or Contains An Ammonium Ion Patents (Class 528/388)
  • Patent number: 5391646
    Abstract: 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: Grant
    Filed: May 20, 1993
    Date of Patent: February 21, 1995
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Yoshikatsu Satake, Yoshiyuki Inaguma, Yasuhiro Suzuki
  • Patent number: 5391645
    Abstract: 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: Grant
    Filed: May 20, 1993
    Date of Patent: February 21, 1995
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Yoshikatsu Satake, Yoshiyuki Inaguma, Yasuhiro Suzuki
  • Patent number: 5384391
    Abstract: 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: Grant
    Filed: December 27, 1993
    Date of Patent: January 24, 1995
    Assignee: Tosoh Corporation
    Inventors: Hiroshi Miyata, Hiroshi Inoue, Akira Akimoto
  • Patent number: 5380821
    Abstract: 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: Grant
    Filed: June 14, 1993
    Date of Patent: January 10, 1995
    Assignee: Solvay (Societe Anonyme)
    Inventors: Pierre Dournel, Danny Van Hoyweghen, Ardechir Momtaz
  • Patent number: 5374709
    Abstract: 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: Grant
    Filed: October 23, 1992
    Date of Patent: December 20, 1994
    Assignee: Phillips Petroleum Company
    Inventors: Earl Clark, Jr., Lacey E. Scoggins, Glenn F. Kile
  • Patent number: 5367049
    Abstract: 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: Grant
    Filed: August 16, 1993
    Date of Patent: November 22, 1994
    Assignee: Solvay (Societe Anonyme)
    Inventors: Danny Van Hoyweghen, Jean-Marc Coisne
  • Patent number: 5364928
    Abstract: 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: Grant
    Filed: May 14, 1993
    Date of Patent: November 15, 1994
    Assignee: Phillips Petroleum Company
    Inventor: Carlton E. Ash
  • Patent number: 5360890
    Abstract: 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: Grant
    Filed: December 22, 1993
    Date of Patent: November 1, 1994
    Assignee: Tosoh Corporation
    Inventors: Shinji Tanaka, Hiroshi Inoue
  • Patent number: 5354841
    Abstract: A process is provided for producing a poly(arylene sulfide) polymer which employs as a reactant cyclic arylene sulfide oligomers.
    Type: Grant
    Filed: August 9, 1993
    Date of Patent: October 11, 1994
    Assignee: Phillips Petroleum Company
    Inventors: Jon F. Geibel, Carlton E. Ash
  • Patent number: 5352768
    Abstract: 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: Grant
    Filed: October 23, 1992
    Date of Patent: October 4, 1994
    Assignee: Phillips Petroleum Company
    Inventors: John D. Stuber, Wei-Teh W. Shang, Lacey E. Scoggins
  • Patent number: 5350833
    Abstract: 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: Grant
    Filed: June 25, 1993
    Date of Patent: September 27, 1994
    Assignee: Tosoh Corporation
    Inventors: Hiroshi Inoue, Toshikazu Kato
  • Patent number: 5350834
    Abstract: 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: Grant
    Filed: May 14, 1993
    Date of Patent: September 27, 1994
    Assignee: Phillips Petroleum Company
    Inventors: Rex L. Bobsein, Michael C. Yu, Roy F. Wright, David A. Soules
  • Patent number: 5342920
    Abstract: 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: Grant
    Filed: December 16, 1992
    Date of Patent: August 30, 1994
    Assignee: Tonen Chemical Corporation
    Inventors: Yoichi Imai, Toshiyuki Hirano, Osamu Komiyama, Hidenori Yamanaka
  • Patent number: 5334701
    Abstract: 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: Grant
    Filed: October 23, 1992
    Date of Patent: August 2, 1994
    Assignee: Phillips Petroleum Company
    Inventors: Carlton E. Ash, Jon F. Geibel, Randy L. Hagenson, David A. Soules
  • Patent number: 5331069
    Abstract: 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: Grant
    Filed: October 27, 1992
    Date of Patent: July 19, 1994
    Assignee: Phillips Petroleum Company
    Inventors: Rex L. Bobsein, Earl Clark, Jr.
  • Patent number: 5331029
    Abstract: 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: Grant
    Filed: June 14, 1993
    Date of Patent: July 19, 1994
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hiroyuki Sato, Kazuhiro Watanabe, Toshiya Watanabe
  • Patent number: 5328980
    Abstract: 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: Grant
    Filed: December 3, 1992
    Date of Patent: July 12, 1994
    Assignee: Phillips Petroleum Company
    Inventors: Owen H. Decker, Michael C. Yu
  • Patent number: 5326851
    Abstract: 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: Grant
    Filed: November 16, 1992
    Date of Patent: July 5, 1994
    Assignee: Bayer AG
    Inventors: Burkhard Kohler, Udo Wolf, Wolfgang Russeler, Wilfried Haese
  • Patent number: 5324814
    Abstract: 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: Grant
    Filed: April 18, 1991
    Date of Patent: June 28, 1994
    Assignee: Kureha Kagaku Kogyo K. K.
    Inventors: Yukichika Kawakami, Mitsuru Hoshino, Yoshikatsu Satake
  • Patent number: 5321121
    Abstract: 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: Grant
    Filed: November 30, 1992
    Date of Patent: June 14, 1994
    Assignee: Phillips Petroleum Company
    Inventors: Michael C. Yu, Jimmie J. Straw
  • Patent number: 5312880
    Abstract: 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: Grant
    Filed: August 30, 1993
    Date of Patent: May 17, 1994
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Hiroyuki Sato, Mitsuru Hoshino, Yukichika Kawakami
  • Patent number: 5312894
    Abstract: 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: Grant
    Filed: April 27, 1993
    Date of Patent: May 17, 1994
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Yukichika Kawakami, Zenya Shiiki
  • Patent number: 5306805
    Abstract: 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: Grant
    Filed: February 10, 1992
    Date of Patent: April 26, 1994
    Assignee: Bayer AG
    Inventors: Wolfgang Arlt, Wolfgang Alewelt, Karl-Heinrich Meyer, Manfred Schmidt, Erhard Tresper, Wolfgang Eisermann
  • Patent number: 5304630
    Abstract: 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: Grant
    Filed: August 30, 1993
    Date of Patent: April 19, 1994
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Hiroyuki Sato, Mitsuru Hoshino, Yukichika Kawakami
  • Patent number: 5304629
    Abstract: 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: Grant
    Filed: August 30, 1993
    Date of Patent: April 19, 1994
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Hiroyuki Sato, Mitsuru Hoshino, Yuichika Kawakami
  • Patent number: 5298574
    Abstract: 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: Grant
    Filed: November 13, 1992
    Date of Patent: March 29, 1994
    Assignee: Phillips Petroleum Company
    Inventor: Dwayne R. Senn
  • Patent number: 5298573
    Abstract: 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: Grant
    Filed: November 13, 1992
    Date of Patent: March 29, 1994
    Assignee: Phillips Petroleum Company
    Inventor: Dwayne R. Senn
  • Patent number: 5296579
    Abstract: 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: Grant
    Filed: February 11, 1988
    Date of Patent: March 22, 1994
    Assignee: Phillips Petroleum Company
    Inventors: Jon F. Geibel, Robert W. Campbell, Guy Senatore, Fernando C. Vidaurri, Mark A. Haney
  • Patent number: 5288848
    Abstract: 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: Grant
    Filed: November 17, 1992
    Date of Patent: February 22, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karsten Idel, Wolfgang Ebert, Ludwig Bottenbruch, Dieter Freitag, Rolf-Volker Meyer
  • Patent number: 5286817
    Abstract: 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: Grant
    Filed: March 5, 1993
    Date of Patent: February 15, 1994
    Assignee: Phillips Petroleum Company
    Inventors: Dwayne R. Senn, Carlton E. Ash
  • Patent number: 5286809
    Abstract: 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: Grant
    Filed: December 9, 1991
    Date of Patent: February 15, 1994
    Assignee: Bayer AG
    Inventors: Hans-Detlef Heinz, Burkhard Kohler
  • Patent number: 5280104
    Abstract: 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: Grant
    Filed: June 30, 1992
    Date of Patent: January 18, 1994
    Assignee: Phillips Petroleum Company
    Inventors: Jon F. Geibel, Harold D. Yelton
  • Patent number: 5278261
    Abstract: 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: Grant
    Filed: December 8, 1992
    Date of Patent: January 11, 1994
    Assignee: Phillips Petroleum Company
    Inventors: Roy F. Wright, Michael C. Yu
  • Patent number: 5278283
    Abstract: 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: Grant
    Filed: January 13, 1992
    Date of Patent: January 11, 1994
    Assignee: Idemitsu Petrochemical Company, Limited
    Inventors: Akira Miyoshi, Minoru Senga
  • Patent number: 5274015
    Abstract: 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: Grant
    Filed: November 24, 1992
    Date of Patent: December 28, 1993
    Assignee: Phillips Petroleum Company
    Inventors: Paul J. Deslauriers, Darryl R. Fahey, Paritosh K. Das
  • Patent number: 5268451
    Abstract: 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: Grant
    Filed: December 3, 1992
    Date of Patent: December 7, 1993
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yo Iizuka, Toshio Hosokawa, Yoshinobu Itoh, Shinji Yamamoto, Kazuo Kusida, Takayuki Katto
  • Patent number: 5268450
    Abstract: 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: Grant
    Filed: November 24, 1992
    Date of Patent: December 7, 1993
    Assignee: Phillips Petroleum Company
    Inventors: Paul J. DesLauriers, Darryl R. Fahey, Paritosh K. Das
  • Patent number: 5268449
    Abstract: 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: Grant
    Filed: November 16, 1992
    Date of Patent: December 7, 1993
    Assignee: Phillips Petroleum Company
    Inventors: Dwayne R. Senn, Rex L. Bobstein, Owen H. Decker, Carlton E. Ash, Darryl R. Fahey, Jon F. Geibel
  • Patent number: 5266680
    Abstract: 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: Grant
    Filed: June 24, 1992
    Date of Patent: November 30, 1993
    Assignee: Phillips Petroleum Company
    Inventor: Jerry O. Reed
  • Patent number: 5264515
    Abstract: 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: Grant
    Filed: December 23, 1991
    Date of Patent: November 23, 1993
    Assignee: Rheox, Inc.
    Inventors: Charles A. Cody, Terrence L. Hartman
  • Patent number: 5262517
    Abstract: 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: Grant
    Filed: March 27, 1992
    Date of Patent: November 16, 1993
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Hiroyuki Sato, Mitsuru Hoshino, Yukichika Kawakami
  • Patent number: 5262137
    Abstract: A method for recovery of lithium chloride wherein a dihalogen aromatic compound is reacted with an alkali metal sulfide and/or an alkali metal hydrosulfide in a polar solvent in the presence of lithium chloride and wherein after polyarylene sulfide particles and a matter insoluble in the solvent are separated from the resulting mixture, lithium chloride is recovered from a residual solution, characterized in that lithium chloride in the residual solution is separated on crystallization. In this manner, high purity lithium chloride may be recovered at a lower cost by a simple equipment, whilst high quality polyarylene sulfide may be obtained.
    Type: Grant
    Filed: September 27, 1991
    Date of Patent: November 16, 1993
    Assignee: Idemitsu Petrochemical Co., Ltd.
    Inventors: Hidetoshi Suzuki, Yoshinari Koyama
  • Patent number: 5256763
    Abstract: Disclosed herein is a process for the production of a granular poly(arylene thioether) copolymer by polymerizing an alkali metal sulfide with dihalo-aromatic compounds including at least one dihalo-aromatic carboxylic acid in a polar solvent containing water. Upon the polymerization, at least a part of the dihalo-aromatic carboxylic acid is converted into an alkaline earth metal salt in advance, the hydroxide and/or oxide of an alkaline earth metal is added together with the dihalo-aromatic carboxylic acid to the polymerization reaction system, or the hydroxide and/or oxide of an alkaline earth metal is added together with an alkaline earth metal salt of the dihalo-aromatic carboxylic acid and the dihalo-aromatic carboxylic acid to the polymerization reaction system.
    Type: Grant
    Filed: November 26, 1991
    Date of Patent: October 26, 1993
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Mitsuru Hoshino, Yukichika Kawakami, Takayuki Katto
  • Patent number: 5256743
    Abstract: Disclosed herein is a poly(arylene thioether) resin composition comprising 100 parts by weight of a poly(arylene thioether) (A) having a shear rate dependence value of melt viscosity at 310.degree. C. of 2.2-3.0 and a crystallization temperature of 175.degree.-210.degree. C., and 20-400 parts by weight of a poly(arylene thioether) (B) having a shear rate dependence value of melt viscosity at 310.degree. C. of 1.0-2.0 and a crystallization temperature of 220.degree.-260.degree. C. The resin portion consisting of the poly(arylene thioethers) (A) and (B) in the resin composition has a melt viscosity of 1,400-3,500 poises as measured at 310.degree. C. and a shear rate of 1,200 sec.sup.-1, a shear rate dependence value of melt viscosity at 310.degree. C. of 1.5-2.3, and a crystallization temperature of 205.degree.-230.degree. C. Extruded products such as a tubular extruded article obtained from the resin composition are also disclosed.
    Type: Grant
    Filed: February 13, 1991
    Date of Patent: October 26, 1993
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Toshio Enoki, Yasuo Sakaguchi
  • Patent number: 5256742
    Abstract: A process for preparing a poly(arylene sulfide) and copolymer thereof from a poly(arylene sulfide disulfide) is provided which comprises contacting the poly(arylene sulfide disulfide) with a polyhalo-substituted cyclic compound having unsaturation between adjacent ring carbon atoms and having halogen atoms attached to the ring carbon atoms in a polar organic compound and a basic compound at an elevated temperature. Alternatively, the poly(arylene sulfide disulfide) can be substantially dissolved in the polar organic solvent at elevated temperature to form fragments which can be contacted with the polyhalo-substituted cyclic compound in a polar organic compound and a basic compound at an elevated temperature. The fragments also can be isolated, recovered and then contacted with the polyhalo-substituted cyclic compound in a polar organic compound and a basic compound at an elevated temperature.
    Type: Grant
    Filed: October 8, 1992
    Date of Patent: October 26, 1993
    Assignee: Phillips Petroleum Company
    Inventors: William E. Sattich, Owen H. Decker, Dwayne R. Senn, Darryl R. Fahey
  • Patent number: 5247030
    Abstract: This invention relates to polyarylene sulphides (PAS), preferably polyphenylene sulphides (PPS), which are modified with carboxyl groups or dicarboxylic acid anhydride groups.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: September 21, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Burkhard Kohler, Hans-Detlef Heinz, Klaus Reinking
  • Patent number: 5247002
    Abstract: This is invention relates to thermoplastic compositions of polyphenylene sulphide with an addition of silver nitrate which have improved crystallization properties and to a process for their preparation.
    Type: Grant
    Filed: September 16, 1992
    Date of Patent: September 21, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Udo Wolf, Eckhard Wendt, Burkhard Kohler, Bahman Sarabi
  • Patent number: 5247063
    Abstract: This invention relates to a process for the purification of optionally branched polyarylene sulphides (PPS). Polyarylene sulphides which have been purified according to the invention are distinguished by the reduced amount of ash-forming impurities contained in them.
    Type: Grant
    Filed: June 12, 1992
    Date of Patent: September 21, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Alewelt, Franz Alfes, Wolfgang Eisermann, Erhard Tresper
  • Patent number: 5241043
    Abstract: A process for preparing a granular polyarylene sulfide having a high molecular weight is a one-stage polycondensation process which involves subjecting a dihalogen aromatic compound to polycondensation with a source of sulfur in the presence of a polymerization aid in an organic polar solvent and setting the temperature for polycondensation to a range from 220.degree. C. to 248.degree. C. for a predetermined period of time prior to completion of polycondensation up to completion of polycondensation. The resulting granular polyarylene sulfide is suitable for molding or forming into sheets, films, fibers and so on, causes less burrs when subjected to injection molding, has a high molecular weight sufficient to create the property of forming a gel, and is easy to handle.
    Type: Grant
    Filed: December 24, 1990
    Date of Patent: August 31, 1993
    Assignee: Idemitsu Petrochemical Company, Ltd.
    Inventor: Minoru Senga
  • Patent number: 5239054
    Abstract: The nuisance metal-corrosive property is effectively lowered by mixing an heating polyarylene sulfide resins with (i) zinc carbonate; (ii) zinc carbonate and an alkaline earth metal chloride; (iii) zinc oxide and/or hydroxide; or (iv) zinc oxide and/or hydroxide, and an alkaline earth metal chloride in the presence of a good solvent for the resins.
    Type: Grant
    Filed: December 17, 1991
    Date of Patent: August 24, 1993
    Assignee: Tosoh Corporation
    Inventors: Toshihiko Muneto, Toshikazu Kato, Hiroshi Inoue