Polymerizing In The Presence Of A Specified Material Other Than A Reactant Patents (Class 528/222)
  • Patent number: 5274071
    Abstract: A wholly aromatic polyamide capable of being dissolved in organic solvents to form an isotropic dope solution and having an excellent chemical resistance, heat resistance, processability and mechanical strength and a high modulus, comprises recurring aromatic dicarbonyl units of the formulae: ##STR1## and recurring aromatic diamine units of the formulae: ##STR2## wherein R and R' are a hydrogen or halogen atom or an alkyl or alkoxyl radical, n is 1 to 3, and p and q are 1 to 4.
    Type: Grant
    Filed: February 1, 1991
    Date of Patent: December 28, 1993
    Assignee: Teijin Limited
    Inventors: Toshihiro Santa, Tsutomu Kiriyama
  • Patent number: 5274051
    Abstract: Novel carbonyl containing compositions are prepared by contacting, in the presence of a free radical initiator, a first compound selected from the group consisting of saturated hydrocarbons, substituted saturated hydrocarbons, polymers and mixtures thereof with a carbonyl containing compound or mixtures thereof having the structure: ##STR1## where X and Y are independently selected from OH, OR.sub.1, NR.sub.1 R.sub.2 and R.sub.1 wherein R.sub.1 and R.sub.2 are selected independently from the group consisting of aryl radicals or alkyl radicals of from 1 to 18 carbon atoms.
    Type: Grant
    Filed: November 5, 1992
    Date of Patent: December 28, 1993
    Assignee: Exxon Research & Engineering Company
    Inventors: Stanley J. Brois, Jacqueline Ogletree
  • Patent number: 5266365
    Abstract: The present invention is directed to an epoxy-containing polymeric material having nonlinear optical properties, particularly a glycidyl amine polymer, and a process for making the nonlinear optical (NLO) epoxy-containing polymeric material including poling the polymeric material under high voltage at elevated temperature for a period of time to bring about orientation of the nonlinear optical functionalities in the polymer. The polymers have enhanced thermal stability and good NLO properties.
    Type: Grant
    Filed: February 28, 1992
    Date of Patent: November 30, 1993
    Assignee: The Dow Chemical Company
    Inventors: John J. Kester, H. Craig Silvis
  • Patent number: 5264176
    Abstract: An aromatic sulfide/ketone polymer is prepared from a dihaloaromatic ketone, alkali metal sulfide, water and a polar organic compound. The polymerization reaction mixture is subjected to a heat soak at an elevated temperature, then a separation agent is added under controlled conditions and the mixture is subsequently cooled to provide a mixture comprising particulate aromatic sulfide/ketone polymer. Biaxially-oriented film is made from the recovered particles of aromatic sulfide/ketone polymer by (1) washing the polymer particles with an aqueous calcium salt, (2) heating the washed particles to remove water, (3) molding the heated particles to form a sheet of polymer, (4) biaxially stretching the sheet above the glass transition temperature of the polymer to form a film, and (5) heat-setting the biaxially-oriented film under stretching tension for a time and at a temperature to increase strength properties and density.
    Type: Grant
    Filed: November 26, 1991
    Date of Patent: November 23, 1993
    Assignee: Phillips Petroleum Company
    Inventors: Michael D. Cliffton, Jerry O. Reed, Rex L. Bobsein, Jon F. Geibel
  • Patent number: 5260412
    Abstract: A terminal-modified imide oligomer composition, comprising(A) 100 parts by weight of a terminal-modified imide oligomer obtained by a reaction in a solvent of a biphenyltetracarboxylic acid compound with an aromatic diamine compound and a monoamine compound containing a carbon-carbon triple bond, and having an unsaturated terminal group at the terminal of the oligomer and an imide bond in the oligomer, and having a logarithmic viscosity number at 30.degree. C., as determined at a concentration of 0.5 g/100 ml of N-methyl-2-pyrrolidone as a solvent, of from 0.1 to 1 and;(B) 5 to 180 parts by weight of an unsaturated imide compound obtained by a reaction in a solvent of a substituent-containing nadic anhydride with a monoamine compound having a carbon-carbon triple bond in an equimolar ratio, and having an unsaturated terminal group at the terminal thereof and an imide bond therein.
    Type: Grant
    Filed: September 24, 1990
    Date of Patent: November 9, 1993
    Assignee: Ube Industries, Ltd.
    Inventors: Shinji Yamamoto, Hideho Tanaka, Kazuyoshi Fujii
  • Patent number: 5248760
    Abstract: The invention comprises curing polyamic acid solutions into polyimide solutions by adding a hydrophilic reagent to a polyamic acid solution. The hydrophilic reagent is selected to have little or no reactivity with amines or carboxylic acids, and is of the type that will react with water to form by-products that shift the equilibrium between polyamic acid as a reactant and polyimide and water as products toward the production of polyimide.
    Type: Grant
    Filed: January 25, 1991
    Date of Patent: September 28, 1993
    Assignees: UNC at Charlotte, MCNC
    Inventors: Thomas D. DuBois, Farid M. Tranjan, Stephen M. Bobbio
  • Patent number: 5214127
    Abstract: A process for the preparation of aromatic polyamides comprises reacting carbon monoxide and an aromatic iodoamine characterized by having at least one iodine atom covalently bonded to an aromatic ring and at least one amino group. The process is conducted in the presence of a solvent, a catalyst and a base at a pressure greater than about 1 kg/cm.sup.2.
    Type: Grant
    Filed: February 25, 1992
    Date of Patent: May 25, 1993
    Assignee: Eastman Kodak Company
    Inventors: Robert J. Perry, S. Richard Turner, Richard W. Blevins
  • Patent number: 5212261
    Abstract: Latent, heat-curable epoxy resin compositions containing metal carboxylate curing systems provide exceptional latency, particularly at elevated temperature, as well as facile curing, high T.sub.g and adhesive strength, and other attractive properties. The metal carboxylates comprise alkali metals and alkaline earth metals, aromatic and aliphatic metal carboxylates. The preferred curing systems comprise synergistic combinations of the metal carboxylates with cure modifiers.
    Type: Grant
    Filed: December 17, 1990
    Date of Patent: May 18, 1993
    Assignee: Henkel Research Corporation
    Inventor: Thomas J. Stierman
  • Patent number: 5194563
    Abstract: Linear aromatic polymeric species, particularly oligomers and polymers are produced under mild conditions in good yield by reacting an at least binuclear aromatic compound with an alkylidene bisphenol in the presence of a non C-alkylatable hydroxy substituted aromatic compound effective to stabilize a generated carbonium ion intermediate; the alkylidene bisphenol may be formed in situ from a ketone or aldehyde in the presence of a catalytic amount of a hydroxy substituted aromatic compound effective to generate a carbonium ion with the ketone or aldehyde; carrying out the reaction under reduced pressure, particularly high vacuum permits direct production of high polymers; the oligomers are useful in the manufacture of high molecular weight engineering or industrial plastics; the polymers may be used directly as such plastics.
    Type: Grant
    Filed: April 2, 1991
    Date of Patent: March 16, 1993
    Inventor: Allan S. Hay
  • Patent number: 5173561
    Abstract: The present invention relates to a novel class of aromatic diamine monomers, benzoxazole polymers made from said class of monomers, and polymer-matrix composites which may be produced therefrom. The present invention also relates to methods of producing said polymers and said polymer-matrix composites. The polymer-matrix composites have as one advantage high strength and temperature resistance.
    Type: Grant
    Filed: July 24, 1990
    Date of Patent: December 22, 1992
    Assignee: Daychem Laboratories, Inc.
    Inventor: Rakesh K. Gupta
  • Patent number: 5171821
    Abstract: A process for preparing a metal phenolate of the formula II:Cl--Ar.sub.1 COAr.sub.2 OM (II)wherein each of Ar.sub.1 and Ar.sub.2 which may be the same or different is a bivalent group of the formula: ##STR1## wherein each of R.sup.1 and R.sup.12 is a hydrogen atom, a halogen atom, an alkoxy group, a phenoxy group, an alkyl group, a cycloalkyl group, a phenyl group, an aralkyl group, an acyl group, a nitrile group, a nitro group or an acyloxy group, each of Y and Z is an oxygen atom or a ketone group, and each of n and m is an integer of from 0 to 4, and M is an alkali metal, which comprises reacting a phenol compound of the formula I:Cl--Ar.sub.1 COAr.sub.2 OH (I)wherein Ar.sub.1 and Ar.sub.2 are as defined above, with an alkali metal compound in the presence of water, and then removing water, characterized in that water is azeotropically distilled off together with an organic solvent capable of forming an azeotropic mixture with water.
    Type: Grant
    Filed: May 31, 1989
    Date of Patent: December 15, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Seiichi Nozawa, Hiroshi Noguchi, Fumitoshi Sakaguchi, Yuko Mihara
  • Patent number: 5164476
    Abstract: Soluble and/or fusible polyimides or polyamidoimides of the general formula I ##STR1## in which R denotes a divalent radical of the formula II ##STR2## Ar denotes trivalent or tetravalent aromatic radicals or mixtures thereof, X denotes the amide radical, if Ar is trivalent, and if Ar is tetravalent denotes the imide radical and R.sub.1 denotes divalent aromatic radicals, and a process for their preparation.
    Type: Grant
    Filed: June 12, 1990
    Date of Patent: November 17, 1992
    Assignee: Chemie Linz Gesellschaft m.b.H.
    Inventors: Gerd Greber, Heinrich Gruber, Marcel Sychra
  • Patent number: 5162483
    Abstract: The invention provides aromatic polyamides having an improved resistance to thermo-oxidation. This is achieved by carrying out the polycondensation in the presence of a catalyst system which comprises a mixture of a phosphorus compound and a tin(II) compound or is a compound which contains both elements. The process according to the invention allows aromatic polyamides to be obtained which are resistant to thermo-oxidation (discoloration).
    Type: Grant
    Filed: October 24, 1990
    Date of Patent: November 10, 1992
    Assignee: Huels Aktiengesellschaft
    Inventors: Gunter Poll, Martin Bartmann, Jurgen Finke
  • Patent number: 5130411
    Abstract: An improved process for preparing increased molecular weight polyarylene sulfides is disclosed. The process comprises at least two stages: a first polymerization stage in which a polymer of a relatively low molecular weight is prepared and a second polymerization stage in which the molecular weight is substantially increased. The increased molecular weight permits the polymer to be used in a wide range of molding and shaping applications.
    Type: Grant
    Filed: March 6, 1991
    Date of Patent: July 14, 1992
    Assignee: Tosoh Corporation
    Inventors: Shinji Tanaka, Hiroshi Inoue
  • Patent number: 5128444
    Abstract: A thermosetting resin composition, a solution composition of the resin and a thermosetting dry film formed out of the resin are disclosed. The thermosetting resin composition contains a specific resin component as the main component. The resin component consists of (A) 100 weight parts of an aromatic polyimide; and (B) 5 to 2,000 weight parts of (a) a terminal-modified imide oligomer or (b) an unsaturated imide compound. The aromatic polyimide (A) is formed from a tetracarboxylic acid ingredient which contains 2,3,3',4'-biphenyltetracarboxylic acid or its derivative in an amount of at least 60 mole % and an aromatic diamine ingredient. The polyimide has such a high molecular weight that the logarithmic viscosity (concentration: 0.5 g/100 ml of solvent; solvent: N-methyl-2-pyrrolidone; and temperature of measurement: 30.degree. C.) is not less than 0.2. The polyimide is soluble in an organic polar solvent.
    Type: Grant
    Filed: April 17, 1990
    Date of Patent: July 7, 1992
    Assignee: Ube Industries, Ltd.
    Inventors: Hiroshi Inoue, Tadao Muramatsu, Tetsuji Hirano
  • Patent number: 5115078
    Abstract: A polyphenylquinoxaline which consists of 1 to 100 mole percent of structural elements of the formula (IV) ##STR1## and of 0-99 mole percent of the following repeat unit of formula (V) ##STR2## where R is selected from the group consisting of H, an alkyl group, a carbocyclic aromatic group, a heterocyclic aromatic group, or an alkoxy group, Ar.sub.1 is a carbocyclic aromatic or heterocyclic aromatic group, and B is selected from the representative group consisting of:Ar.sub.2 --Z--Ar.sub.3 (i)where Ar.sub.2 and Ar.sub.3 are the same or different carbocyclic aromatic or heterocyclic aromatic group and Z is selected from the representative group consisting of CO, SO or SO.sub.2 ;Z'--Ar.sub.4 --Z' (ii)where Z' is an activated carbocyclic aromatic or heterocyclic aromatic group and Ar.sub.4 is an aliphatic group, a carbocyclic aromatic or heterocyclic aromatic group. A process for manufacture a self polymerizable phenylquinoxaline subject to polymerization by aromatic nucleophilic substitution.
    Type: Grant
    Filed: February 4, 1991
    Date of Patent: May 19, 1992
    Assignee: The University of Akron
    Inventors: Frank W. Harris, Joseph E. Korleski
  • Patent number: 5089596
    Abstract: Aromatic sulfide/ketone polymer is prepared from dihaloaromatic ketone, alkali metal sulfide, water and a polar organic compound. The polymerization reaction mixture comprising the aromatic sulfide/ketone polymer is subjected to a heat soak at elevated temperature then a separation agent (non-solvent) is added under controlled conditions and subsequently cooled to provide a mixture comprising particulate aromatic sulfide/ketone polymer.
    Type: Grant
    Filed: May 22, 1990
    Date of Patent: February 18, 1992
    Assignee: Phillips Petroleum Company
    Inventors: Michael D. Cliffton, Jerry O. Reed, Rex L. Bobsein, Jon F. Geibel
  • Patent number: 5066775
    Abstract: The invention relates to new sulphur-containing copolymers, a process for their preparation from a sulphur source and a mixture of dihalogenoaromatics and dihalogenoaliphatics and their use for the production of shaped articles.
    Type: Grant
    Filed: February 5, 1990
    Date of Patent: November 19, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ernst-Ulrich Dorf, Klaus Reinking, Wolfgang Jakob, Erhard Tresper, Wolfgang Russeler
  • Patent number: 5064933
    Abstract: Benzophenone-type polyimides having repeating groups of the formula ##STR1## where Y and Y' are the same or different and are a chemical bond, --O--, --S--, ##STR2## --CH.sub.2 --, --C(CH.sub.3).sub.2 --, --CF.sub.2, --C(CF.sub.3).sub.2 -- or --Si(CH.sub.3).sub.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: November 12, 1991
    Assignee: Ethyl Corporation
    Inventor: Mark W. Beltz
  • Patent number: 5064932
    Abstract: Novel poly(keto-esters) having carbonyl and oxycarbonyl units randomly combined with linking units derived from olefinic monomers to form an essentially straight-chain polymer backbone are provided. The poly(keto-esters) are produced by converting a portion of the carbonyl functionality of a polyketone to oxycarbonyl groups. The conversion is achieved by reacting the polyketone with an organic peroxyacid in an inert liquid medium at a temperature from -20.degree. C. to 150.degree. C.
    Type: Grant
    Filed: March 26, 1990
    Date of Patent: November 12, 1991
    Assignee: Quantum Chemical Corporation
    Inventors: Biau-Hung Chang, Lester Y. Lee, Jack Kwiatek
  • Patent number: 5061783
    Abstract: The process of the present invention includes first treating a polyamide-acid (such as LARC-TPI polyamide-acid) in an amide-containing solvent (such as N-methylpyrrolidone) with an aprotic organic base (such as triethylamine), followed by dehydrating with an organic dehydrating agent (such as acetic anhydride). The level of crystallinity in the linear aromatic polyimide so produced is maximized without any degradation in the molecular weight thereof.
    Type: Grant
    Filed: April 30, 1990
    Date of Patent: October 29, 1991
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Terry L. St. Clair
  • Patent number: 5055549
    Abstract: The present invention is connected with a process for preparing a novel photosensitive polyimide precursor having excellent shelf stability and high sensitivity and containing less impurities.The process for preparing a photosensitive heat-resistant polymer containing a repeating unit represented by the formula (III) comprises the step of reacting a photosensitive group-containing isoimide represented by the formula (I) with a diamine represented by the formula (II) at a temperature of 0.degree. to 100.degree. C. in the presence of a solvent: ##STR1## wherein R.sup.1 is independently a tetravalent carbon cyclic aromatic group or heterocyclic group; R.sup.2 is independently an aliphatic group having at least 2 carbon atoms, an alicyclic group, an aromatic aliphatic group, a carbon cyclic aromatic group, a heterocyclic group or a polysiloxane group; R.sup.3 is a monovalent organic group having a photosensitive unsaturated group; and D is an oxygen atom or .dbd.N--R.sup.3.
    Type: Grant
    Filed: January 8, 1990
    Date of Patent: October 8, 1991
    Assignee: Chisso Corporation
    Inventors: Hirotoshi Maeda, Kouichi Kunimune
  • Patent number: 5041524
    Abstract: Polyphosphazene derivatives containing carbonyl groups which are apt to undergo rapid photoreticulation processes having the general formula ##STR1## in which: X represents substituents bound to the polyphosphazene chains by means of hydroxy or amino functions, and containing carbonyl groups;X' represents additional substituents bound to the polyphosphazene chain through hydroxy or amino functions and containing one or more easily extractable hydrogen atoms;(w+y+z) is an integer between 20 and 15,000;w and z are integers greater than or equal to 0 and always lower than 15.000;y is an integer between 20 and 15,000.
    Type: Grant
    Filed: November 16, 1989
    Date of Patent: August 20, 1991
    Assignee: Consiglio Nazionale Delle Ricerche
    Inventors: Mario Gleria, Francesco Minto, Lucia Flamigni
  • Patent number: 5030704
    Abstract: A polyphenylquinoxaline which consists of 1 to 100 mole percent of structural elements of the formula (IV) ##STR1## and of 0-99 mole percent of the following repeat unit of formula (V) ##STR2## where R is selected from the group consisting of H, an alkyl group, a carbocyclic aromatic group, a heterocyclic aromatic group, or an alkoxy group, Ar.sub.1 is a carbocyclic aromatic or heterocyclic aromatic group, and B is selected from the representative group consisting of:Ar.sub.2 --Z--Ar.sub.3 (i)where Ar.sub.2 and Ar.sub.3 are the same or different carbocyclic aromatic or heterocyclic aromatic group and Z is selected from the representative group consisting of CO, SO or SO.sub.2 ;Z'--Ar.sub.4 --Z' (ii)where Z' is an activated carbocyclic aromatic or heterocyclic aromatic group and Ar.sub.4 is an aliphatic group, a carbocyclic aromatic or heterocyclic aromatic group. A process for manufacture a self polymerizable phenylquinoxaline subject to polymerization by aromatic nucleophilic substitution.
    Type: Grant
    Filed: June 20, 1989
    Date of Patent: July 9, 1991
    Assignee: The University of Akron
    Inventors: Frank W. Harris, Joseph E. Korleski
  • Patent number: 5025084
    Abstract: A polyimide-forming composition comprising(A) a polycarboxylic acid partial ester of formulaHOOC--R.sup.1 --COOR.sup.2 Iwhere R.sup.1 denotes a divalent ethylenically unsaturated aliphatic or cycloaliphatic group of 2 to 20 carbon atoms, and R.sup.2 denotes the residue, after removal of a hydroxyl group, of an alcohol having from 4 to 20 carbon atoms which has a cycloaliphatic, aromatic or heterocyclic ring and is polymerizable on heating in the presence of an acid,(B) a partial ester of formula I above in which R.sup.1 denotes a group of formula II ##STR1## where Ar.sup.1 denotes a tetravalent aromatic group of 6 to 20 carbon atoms linked through aromatic carbon atoms thereof to the indicated carbon atoms, and R.sup.2 is as defined above,(C) an aromatic primary polyamine and(D) a heat-activable substance which releases an acid at a temperature of 100.degree. C. or above.
    Type: Grant
    Filed: July 10, 1990
    Date of Patent: June 18, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Bryan Dobinson, Mark R. Southcott
  • Patent number: 5011907
    Abstract: Highly conjugated organic polymers typically have large non-resonant electronic susceptibilities, which give the molecules unusual optical properties. To enhance these properties, "defects" are introduced into the polymer chain. Examples include light doping of the conjugated polymer and synthesis, conjugated polymers which incorporate either electron donating or accepting groups, and conjugated polymers which contains a photoexcitable species capable of reversibly transferring its electron to an acceptor. Such defects in the chain permit enhancement of the second hyperpolarizability by at least an order of magnitude.
    Type: Grant
    Filed: October 10, 1989
    Date of Patent: April 30, 1991
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: David N. Beratan
  • Patent number: 4999420
    Abstract: This invention relates to a process for the production of aromatic polycarbonates from cyclic aromatic carbonate oligomers in the presence of aprotic organic solvents at low temperatures.
    Type: Grant
    Filed: September 14, 1989
    Date of Patent: March 12, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Edgar Leitz, Ludwig Bottenbruch, Karl-Heinz Ott, Alfred Jung, Ulrich Grigo
  • Patent number: 4996268
    Abstract: A carbinol-containing polyimide oligomer terminated with epoxide-reactive end groups has the structure ##STR1## wherein Ar is ##STR2## R.sup.1 and R.sup.2 are independently divalent organic radicals; R.sup.3 is a trivalent organic radical; Y is an epoxide-reactive group (e.g.); m is 0 or 1 and n is 0-10. Suitable epoxide-reactive groups include a phenol, thiol, amine, or carboxyl group. Polyimide-polyepoxide adducts are prepared by reacting the polyimides with a polyepoxide, preferably a diepoxide used in excess. The polyimide oligomers are useful as coatings or adhesives. The adducts are useful as adhesives, for composites, and particularly for impregnating the fiberglass sheets which are used to form circuit boards.
    Type: Grant
    Filed: February 17, 1989
    Date of Patent: February 26, 1991
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventor: Jules E. Schoenberg
  • Patent number: 4963645
    Abstract: A terminal-modified imide oligomer having an unsaturated group as a terminal group and an imide bond inside of the oligomer which is produced by reacting 2,3,3',4'-or 3,3',4,4'-biphenyltetracarboxylic acid or its derivative, a diamine compound, and an unsaturated dicarboxylic acid or its derivative and/or an unsaturated monoamine in an organic solvent is disclosed. This oligomer has a logarithmic viscosity of not more than 1.0. This logarithmic viscosity is measured under the conditions of concentration of 0.5 g/100 ml-solvent (N-methyl-2-pyrrolidone) and a temperature of 30.degree. C., and has a melting point of 50.degree. to 300.degree. C.
    Type: Grant
    Filed: August 24, 1988
    Date of Patent: October 16, 1990
    Assignee: Ube Industries, Ltd.
    Inventors: Hiroshi Inoue, Tadao Muramatsu, Tetsuji Hirano
  • Patent number: 4952666
    Abstract: Polyimide polymers having a relatively low dielectric constant and good solvent resistance, are formed by polymerization of a polyimide oligomer having the formula ##STR1## wherein R is selected from the group consisting of: --C.tbd.CH,--CH.dbd.CH.sub.2,--CN, and ##STR2## wherein R.sub.1 is --H or --CH.sub.3, and n=1-20. Preferably R is an acetylene group. These polymers may also be formed from the corresponding polyamic acid oligomers.These polymers are useful for forming dielectric layers, particularly in multilayer semiconductor devices.
    Type: Grant
    Filed: May 6, 1988
    Date of Patent: August 28, 1990
    Assignee: Hughes Aircraft Company
    Inventor: Abraham L. Landis
  • Patent number: 4946931
    Abstract: Polymers are provided that are useful for making biodegradable sustained release agent dispensers and which contain at least one of the following mer units (I) and (II) ##STR1## wherein X is a quadrivalent organic grouping, A and B are hydrogen or lower alkyl, and R is hydrocarbyl or oxyhydrocarbyl of 1 to 14 carbon atoms and, if oxyhydrocarbyl, containing 1 to 4 oxy groups, and may be either aliphatic or aryl, unsubstituted or substituted with one or more lower alkyl, amino, nitro or halogen moieties. Methods of synthesizing the novel polymers are also provided, as biodegradable beneficial agent dispensers prepared using the novel polymers.
    Type: Grant
    Filed: June 14, 1989
    Date of Patent: August 7, 1990
    Assignee: Pharmaceutical Delivery Systems, Inc.
    Inventors: Jorge Heller, Steve Y. W. Ng, Donald W. H. Penhale
  • Patent number: 4929711
    Abstract: A facile process for converting polyketones to polyesters is provided. The process involves reacting a polyketone, such as an ethylene-carbon monoxide copolymer, with an organic peroxyacid oxidizing agent in an inert liquid medium at a temperature from -20.degree. C. to 150.degree. C. to convert substantially all or only a portion of the keto functionality to ester moieties.
    Type: Grant
    Filed: October 4, 1989
    Date of Patent: May 29, 1990
    Assignee: Quantum Chemical Corporation
    Inventors: Biau-Hung Chang, Lester Y. Lee, Jack Kwiatek
  • Patent number: 4912195
    Abstract: A process for producing an aromatic polyketone which comprises polymerizing an appropriate monomer or monomers by a Friedel-Crafts polymerization reaction using a Lewis acid catalyst. A controlling agent such as a Lewis base may be added to the reaction medium and/or the reaction is conducted under specified conditions to control the reaction. The reaction medium comprises, for example, aluminum trichloride as the Lewis acid, an organic Lewis base such as N,N-dimethylformamide or an inorganic Lewis base such as sodium or lithium chloride, and a diluent such as methylene chloride or dichloroethane. The amount of Lewis acid, the amount of Lewis base, the temperature of the reaction and the monomer to diluent molar ratio are varied depending on the monomer system to obtain melt-processable, high molecular weight, substantially linear polymers, for example poly(carbonyl-p-phenylene-oxy-p-phenylene), poly(carbonyl-p-phenylene-oxy-p-phenylene-oxy-p-phenylene), and the like.
    Type: Grant
    Filed: July 6, 1989
    Date of Patent: March 27, 1990
    Assignee: Raychem Corporation
    Inventors: Viktors Jansons, Heinrich C. Gors
  • Patent number: 4895893
    Abstract: Heat-resistant resin composition comprising (A) 100 parts by weight of a poly(arylene sulfide) of a substantially linear structure containing 50% by weight or higher of recurring units of the formula ##STR1## and a logarithmic viscosity number of 0.1 to 1.0 dl/g; (B) from 0.01 to less than 25 parts by weight of a melt-stable poly(arylene thioether-ketone) having predominant recurring units of the formula ##STR2## wherein the --CO-- and --S-- are in the para position to each other, and having a melting point of 310.degree.-380.degree. C., a residual melt crystallization enthalpy of at least 10 J/g, a melt crystallization temperature of at least 210.degree. C. and a reduced viscosity of 0.2 to 2 dl/g; and (C) at least one of fibrous fibers and/or at least one of inorganic fillers in a proportion of 0 to 400 parts by weight per 100 parts by weight of the resin component comprising said poly(arylene sulfide) and said poly(arylene thioether-ketone).
    Type: Grant
    Filed: May 12, 1988
    Date of Patent: January 23, 1990
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Yoshikatsu Satake, Takashi Kaneko, Yutaka Kobayashi, Yukio Ichikawa, Yo Iizuka, Makoto Fukuda, Toshio Enoki, Takayuki Katto, Yasuo Sakaguchi, Zenya Shiiki
  • Patent number: 4895892
    Abstract: Disclosed herein is a melt-stable poly(arylene thioether-ketone) composition, which comprises:(A) 100 parts by weight of a melt-stable poly(arylene thioether-ketone) having predominant recurring units of the formula ##STR1## and having a melting point, Tm of 310.degree.-380.degree. C., a residual melt crystallization enthalpy, .DELTA.Hmc (420.degree. C./10 min) of at least 10 J/g, a melt crystallization temperature, Tmc (420.degree. C./10 min) of at least 210.degree. C. and a reduced viscosity of 0.2-2 dl/g;(B) 0-400 parts by weight of at least one of thermoplastic resins; and(C) at least one of fibrous fillers and/or at least one of inorganic fillers in a proportion of 0-400 parts by weight per 100 parts by weight of the sum of said components (A) and (B).At least either one of the components (B) or (C) is contained in a proportion of at least 0.1 part by weight per 100 parts by weight of the component (A).
    Type: Grant
    Filed: May 12, 1988
    Date of Patent: January 23, 1990
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Yoshikatsu Satake, Takashi Kaneko, Yutaka Kobayashi, Yo Iizuka, Toshitaka Kouyama, Takayuki Katto, Zenya Shiiki
  • Patent number: 4895925
    Abstract: Disclosed herein are a melt-stable poly(arylene thioether-ketone) having predominant recurring units of the formula ##STR1## and having a melting point, Tm of 310.degree.-380.degree. C., a residual melt crystallization enthalpy, .DELTA.Hmc (420.degree. C./10 min) of at least 10 J/g, a melt crystallization temperature, Tmc (420.degree. C./10 min) of at least 210.degree. C., and a reduced viscosity of 0.2-2 dl/g as measured at 25.degree. C. and a polymer concentration of 0.5 g/dl in 98 wt. % sulfuric acid as well as a production process of the poly(arylene thioether-ketone). The poly(arylene thioether-ketone) has melt stability so that conventional melt processing techniques can be applied easily. The poly(arylene thioether-ketone) is a highly-crystalline polymer whose density is at least 1.34 g/cm.sup.3 when annealed at 280.degree. C. for 30 minutes.
    Type: Grant
    Filed: May 12, 1988
    Date of Patent: January 23, 1990
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Yoshikatsu Satake, Takashi Kaneko, Yutaka Kobayashi, Yo Iizuka, Takayuki Katto, Zenya Shiiki
  • Patent number: 4895691
    Abstract: Disclosed herein are poly(arylene thioether-ketone) fibers obtained by melt-spinning a thermoplastic material which comprises 100 parts by weight of a melt-stable poly(arylene thioether-ketone) (PTK) and optionally, up to 50 parts by weight of at least one of thermoplastic resins. The PTK has predominant recurring units of the formula ##STR1## wherein the --CO-- and --S-- are in the para position to each other, and has a melting point, Tm of 310.degree.-380.degree. C., a residual melt crystallization enthalpy, .DELTA.Hmc (420.degree. C./10 min) of at least 10 J/g, a melt crystallization temperature, Tmc (420.degree. C./10 min) of at least 210.degree. C., and a reduced viscosity of 0.3-2 dl/g as determined by viscosity measurement at 25.degree. C. and a polymer concentration of 0.5 g/dl in 98 percent by weight sulfuric acid. The PTK fibers of this invention have high heat resistance and strength.
    Type: Grant
    Filed: May 19, 1989
    Date of Patent: January 23, 1990
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Yoshikatsu Satake, Yo Iizuka, Hiroyuki Endo, Toshitaka Kouyama, Takayuki Katto, Zenya Shiiki
  • Patent number: 4895924
    Abstract: Disclosed herein are poly(arylene thioetherketone) fibers obtained by melt-spinning a thermoplastic material which comprises 100 parts by weight of a melt-stable poly(arylene thioether-ketone) (PTK) and optionally, up to 50 parts by weight of at least one of thermoplastic resins. The PTK has predominant recurring units of the formula ##STR1## wherein the --CO-- and --S-- are in the para position to each other, and has a melting point, Tm of 310-380.degree. C., a residual melt crystallization enthalpy, .DELTA.Hmc (420.degree. C./10 min) of at least 10 J/g, a melt crystallization temperature, Tmc (420.degree. C./10 min) of at least 210.degree. C., and a reduced viscosity of 0.3-2 dl/g as determined by viscosity measurement at 25.degree. C. and a polymer concentration of 0.5 g/dl in 98 percent by weight sulfuric acid. The PTK fibers of this invention have high heat resistance and strength.
    Type: Grant
    Filed: May 12, 1988
    Date of Patent: January 23, 1990
    Assignee: Kureha Kagaku Kogyo K. K.
    Inventors: Yoshikatsu Satake, Yo Iizuka, Hiroyuki Endo, Toshitaka Kouyama, Takayuki Katto, Zenya Shiiki
  • Patent number: 4886871
    Abstract: Disclosed herein are a melt-stable poly(arylene thioether-ketone) having predominant recurring units of the formula ##STR1## and having a melting point, Tm of 310.degree.-380.degree. C., a residual melt crystallization enthalpy, .DELTA.Hmc (420.degree. C./10 min) of at least 10 J/g, a melt crystallization temperature, Tmc (420.degree. C./10 min) of at least 210.degree. C., and a reduced viscosity of 0.2-2 dl/g as measured at 25.degree. C. and a polymer concentration of 0.5 g/dl in 98 wt. % sulfuric acid as well as a production process of the poly(arylene thioether-ketone). The poly(arylene thioether-ketone) has melt stability so that conventional melt processing techniques can be applied easily. The poly(arylene thioether-ketone) is a highly-crystalline polymer whose density is at least 1.34 g/cm.sup.3 when annealed at 280.degree. C. for 30 minutes.
    Type: Grant
    Filed: May 19, 1989
    Date of Patent: December 12, 1989
    Assignee: Kureha Kagaku Kogyo K. K.
    Inventors: Yoshikatsu Satake, Takashi Kaneko, Yutaka Kobayashi, Yo Iizuka, Takayuki Katto, Zenya Shiiki
  • Patent number: 4879366
    Abstract: Aromatic oligomers, in particular arylene ketone and arylene sulfone oligomers, are prepared by reacting an appropriate monomer system in the presence of free Lewis acid and a complex between a Lewis acid, for example, aluminum trichloride, and a Lewis base, for example, N,N-dimethylformamide, and, optionally, a diluent, such as methylene chloride. The process is particularly advantageous for the preparation of substantially or all paralinked arylene ether ketone oligomers as the presence of the Lewis acid/Lewis base complex markedly reduces alkylation and ensures the substantial absence of ortho substitution. The monomer system can be, for example, a self-reacting monomer such as p-phenoxy-benzoyl chloride or a two-monomer system such as 1,4-diphenoxybenzene and terephthaloyl chloride.
    Type: Grant
    Filed: January 11, 1989
    Date of Patent: November 7, 1989
    Assignee: Raychem Corporation
    Inventors: Viktors Jansons, Heinrich C. Gors
  • Patent number: 4873283
    Abstract: Disclosed herein is a molded or formed poly(arylene thioether-ketone) article made of a thermoplastic material which comprises 100 parts by weight of a melt-stable poly(arylene thioether-ketone) (PTK) and if desired, up to 100 parts by weight of at least one of thermoplastic resins and/or up to 300 parts by weight of at least one of fibrous fillers and/or least one of inorganic fillers. The PTK has predominant recurring units of the formula ##STR1## wherein the --CO-- and --S-- are in the para position to each other, and has a melting point, Tm of 310.degree.-380.degree. C., a residual melt cyrstallization enthalpy, .DELTA.Hmc (420.degree. C./10 min) of at least 10 J/g, a melt crystallization temperature, Tmc (420.degree. C./10 min) of at least 210.degree. C., and a reduced viscosity of 0.2-2 dl/g as determined by viscosity measurement at 25.degree. C. and a polymer concentration of 0.5 g/dl in 98 percent by weight sulfuric acid.
    Type: Grant
    Filed: May 12, 1988
    Date of Patent: October 10, 1989
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Yoshikatsu Satake, Yo Iizuka, Toshitaka Kouyama, Takayuki Katto, Zenya Shiiki
  • Patent number: 4857607
    Abstract: The invention relates to polycycloacetals of formula I ##STR1## wherein n is an integer from 1 to 500, x and y are each independently of the other 0 or 1, R.sup.1 is a carbon atom or a tetravalent hydrocarbon radical having a molecular weight not greater than 1000 and which can additionally contain ether oxygen atoms or oxygen atoms in hydroxyl, carbonyl or epoxy groups, and R.sup.2 is a tetravalent hydrocarbon radical derived from a dialdehyde or a diketone.The polycycloacetals can be used together with conventional hardeners and/or curing catalysts for epoxy resins for the fabrication of cross-linked (cured) products having good properties, especially having excellent fastness to solvents, light and weathering.
    Type: Grant
    Filed: May 18, 1988
    Date of Patent: August 15, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Jacques-Alain Cotting, Alfred Renner
  • Patent number: 4857629
    Abstract: A process for preparing a copoly(arylene sulfide) corresponding to the structure[(--A--S--).sub.1-x (--A--S--S--).sub.x ].sub.nwherein x is in the range of 0.5 to 0.001 by reacting a mixture of a diiodoaromatic compound and elemental sulfur in the absence of a basic material and in the presence of a catalytic amount of iron.
    Type: Grant
    Filed: February 13, 1989
    Date of Patent: August 15, 1989
    Assignee: Eastman Kodak Company
    Inventors: Mark Rule, David R. Fagerburg, Joseph J. Watkins
  • Patent number: 4845190
    Abstract: In a process for preparing polyarylene sulfides by reacting a dihalo-aromatic compound with a sulfur source in an organic amide solvent in the presence of an alkali metal salt of carboxylic acid as a polymerization aid or assistant, a specific class of carboxylic acids are employed for preparing the alkali metal salt polymerization aid. The specific carboxylic acids are of the general formula: R(COOH).sub.n (wherein R is a C.sub.1 -C.sub.20 organic radical and n is an integer not less than 1) and have a solubility of not less than 3 g/100 ml in ethanol at 20.degree. C. Use of such a carboxylic acid in the process permits the recovery thereof from the polymerization mixture to be effected with significantly improved efficiency.
    Type: Grant
    Filed: December 24, 1987
    Date of Patent: July 4, 1989
    Assignees: Tosoh Corporation, Toso Susteel Co., Ltd.
    Inventors: Hiroshi Inoue, Toshikazu Kato, Noriaki Emura
  • Patent number: 4841020
    Abstract: Novel copolymers and terpolymers are produced from carbon monoxide, a functionally-substituted ethylenically unsaturated compound wherein the functional substituent is separated from the ethylenic unsaturation by a divalent bridging group of at least one carbon, and optionally an ethylenically unsaturated hydrocarbon. The polymerization is conducted under polymerization conditions in the presence of a catalyst composition formed from a palladium compound, the anion of a non-hydrohalogenic acid having a pKa less than about 6 and a bidentate ligand of phosphorus or of nitrogen.
    Type: Grant
    Filed: September 21, 1987
    Date of Patent: June 20, 1989
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4841011
    Abstract: Friedel Crafts preparation of arylene ether (especially arylene ether ketone) oligomers with an exceptionally high degree of isomeric purity and freedom from by-products can be achieved by adding to the Lewis acid reaction system a protic controlling agent selected from ROX, water, RCOOX, RSO.sub.3 X, and ROY, wherein R is organic, X is hydrogen or metal, and Y is metal.Contrary to conventional expectation, the protic agent does not significantly acylate or alkylate the Friedel Crafts reaction product, and controlling agents of relatively low molecular weight, e.g., benzoic acid, can surprisingly be selected to produce dispersions of the resulting oligomers.
    Type: Grant
    Filed: September 11, 1987
    Date of Patent: June 20, 1989
    Assignee: Raychem Limited
    Inventor: Ian D. H. Towle
  • Patent number: 4841013
    Abstract: Friedel Crafts preparation of arylene ether ketone polymers with an exceptionally high degree of isomeric purity and freedom from by-products can be achieved by adding to the Lewis acid reaction system a protic controlling agent selected from ROX, water, RCOOX, RSO.sub.3 X, and ROY, wherein R is organic, X is hydrogen or metal, and Y is metal. Contrary to conventional expectation, the protic agent does not significantly acylate or alkylate the polymer, and agents of relatively low molecular weight, e.g. benzoic acid, can be selected to produce dispersions of the resulting polymers. The controlling agent also apparently acts to maintain the polymer in solution until a desired molecular weight is reached.
    Type: Grant
    Filed: September 11, 1987
    Date of Patent: June 20, 1989
    Assignee: Raychem Limited
    Inventor: Ian D. H. Towle
  • Patent number: 4831107
    Abstract: A novel class of polymers and processes used in their preparation are described. The polymers are produced by a reaction between polyfunctional amines and quinones. Some are infusible and intractable. Others are eminently suitable for the production of coatings, adhesives, insulators, etc. Some polymers, in solution in appropriate solvents adhere to metals, siliceous materials, composites with sufficient affinity to displace water. The polymers can be cured by heat or chemicals to an impervious and insoluble material that is not wetted by water.
    Type: Grant
    Filed: July 28, 1986
    Date of Patent: May 16, 1989
    Inventor: Semih Erhan
  • Patent number: 4826956
    Abstract: A process for producing a copoly(arylene sulfide) corresponding to the structure[--A--S--).sub.1-x (--A--S--S--).sub.x ].sub.nwherein A is a divalent substituted or unsubstituted aromatic radical, x is in the range of 0.5 to 0.001 and n is at least 200, comprising reacting within a reaction zone a mixture of a diiodoaromatic compound and elemental sulfur at a polymer producing temperature wherein the reaction zone contains an oxygen-containing gas flowing at a rate in the range of 0.001 to 0.08 ft3/hr/mol of oxygen per mole of sulfur.
    Type: Grant
    Filed: May 20, 1988
    Date of Patent: May 2, 1989
    Assignee: Eastman Kodak Company
    Inventors: David R. Fagerburg, Joseph J. Watkins, Paul B. Lawrence, Mark Rule
  • Patent number: RE33545
    Abstract: A process, and product produced therefrom, for preparing a high molecular weight poly(arylene sulfide ketone) from the reaction product of an alkali metal bisulfide with an alkali metal hydroxide, employing molar excess of alkali metal bisulfide with respect to the alkali metal hydroxide. A process, and product produced therefrom, for preparing a high molecular weight poly(arylene sulfide ketone) employing an alkali metal sulfide and an alkali metal hydrosulfide, wherein the alkali metal .[.sulfide.]. .Iadd.hydrosulfide .Iaddend.is added in a molar excess with respect to the alkali metal .[.hydrosulfide.]. .Iadd.sulfide.Iaddend..
    Type: Grant
    Filed: July 14, 1989
    Date of Patent: February 26, 1991
    Assignee: Phillips Petroleum Company
    Inventor: Roger G. Gaughan