Reactant Contains A (o=)s(=o)-halo Group Patents (Class 528/175)
  • Patent number: 5939521
    Abstract: This invention relates the novel diamines, the polyimide oligomers and the polyimides derived therefrom and to the method of preparing the diamines, oligomers and the polyimides. The thermoplastic polyimides derived from the aromatic diamines of this invention are characterized as having a high glass transition temperature, good mechanical properties and improved processability in the manufacture of adhesives, electronic and composite materials for use in the automotive and aerospace industry. The distinction of the novel aromatic diamines of this invention is the 2,2',6,6'-substituted biphenyl radicals which exhibit noncoplanar conformation that enhances the solubility of the diamine as well as the processability of the polyimides, while retaining a realatively high glass transition temperature and improved mechanical properties at useful temperature ranges.
    Type: Grant
    Filed: January 23, 1998
    Date of Patent: August 17, 1999
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Chun-Hua K. Chuang
  • Patent number: 5908915
    Abstract: Copolyetherimides are prepared by the reaction of an alkali metal salt of a dihydroxyaromatic compound with a bis(substituted phthalimide) and a third compound which may be a substituted aromatic ketone or sulfone or a macrocyclic polycarbonate or polyarylate oligomer. The reaction takes place the in presence of a solvent and a phase transfer catalyst having high thermal stability, such as a hexaalkylguanidinium halide. Random or block copolymers may be obtained, depending on the reaction conditions.
    Type: Grant
    Filed: October 6, 1997
    Date of Patent: June 1, 1999
    Assignee: General Electric Company
    Inventor: Daniel Joseph Brunelle
  • Patent number: 5879821
    Abstract: A charge transport polymer including repeat units selected from mers of the formulas ##STR1## and copolymers, and mixtures thereof.
    Type: Grant
    Filed: November 13, 1997
    Date of Patent: March 9, 1999
    Assignee: Xerox Corporation
    Inventor: Bing R. Hsieh
  • Patent number: 5830974
    Abstract: Aromatic polyether polymers, illustrated by polyethersulfones, polyetherketones and polyetherimides, are prepared by a phase transfer catalyzed reaction between a salt of at least one dihydroxyaromatic compound and at least one substituted aromatic compound such as bis(4-chlorophenyl) sulfone, bis(4-chlorophenyl) ketone or 1,3-bis?N-(4-chlorophthalimido)!benzene, in a monoalkoxybenzene such as anisole as diluent and in the presence of a phase transfer catalyst, preferably a hexaalkylguanidinium salt.
    Type: Grant
    Filed: February 13, 1997
    Date of Patent: November 3, 1998
    Assignee: General Electric Company
    Inventors: John Christopher Schmidhauser, Daniel Joseph Brunelle
  • Patent number: 5759449
    Abstract: An optically isotropic film of an aromatic polyethersulfone, which is useful as a substrate for a liquid crystal display device, and an optically anisotropic, uniaxially oriented film of an aromatic polyethersulfone, which is useful as a phase difference plate for a liquid crystal display device. The optically isotropic film is produced by casting an aromatic polyethersulfone solution composition comprising 15 to 40 parts by weight of a solvent which contains at least 60% by weight of 1,3-dioxolane and can dissolve an aromatic polyethersulfone and 10 parts by weight of the aromatic polyethersulfone, on a substrate, and heating the cast solution composition containing a solvent to evaporate the solvent off.
    Type: Grant
    Filed: January 31, 1997
    Date of Patent: June 2, 1998
    Assignee: Teijin Limited
    Inventors: Takashi Shiro, Kaoru Iwata, Hideaki Nitta, Takeshi Sasaki, Utami Yonemura
  • Patent number: 5741408
    Abstract: In order to produce a polymer electrolyte membrane from sulfonated, aromatic polyether ketone, an aromatic polyether ketone of the formula (I) ##STR1## in which Ar is a phenylene ring having p- and/or m-bonds,Ar' is a phenylene, naphthylene, biphenylene, anthrylene or another divalent aromatic unit,X, N and M, independently of one another are 0 or 1,Y is 0, 1, 2 or 3,P is 1, 2, 3 or 4,is sulfonated and the sulfonic acid is isolated. At least 5% of the sulfonic groups in the sulfonic acid are converted into sulfonyl chloride groups, and these are reacted with an amine containing at least one crosslinkable substituent or a further functional group, and unreacted sulfonyl chloride groups are subsequently hydrolyzed. The resultant aromatic sulfonamide is isolated and dissolved in an organic solvent, the solution is converted into a film, and the crosslinkable substituents in the film are then crosslinked.In specific cases, the crosslinkable substituents can be omitted.
    Type: Grant
    Filed: May 19, 1995
    Date of Patent: April 21, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Freddy Helmer-Metzmann, Frank Osan, Arnold Schneller, Helmut Ritter, Konstantin Ledjeff, Roland Nolte, Ralf Thorwirth
  • Patent number: 5668247
    Abstract: The invention provides novel thermoplastic polyimide featuring solid adhesive property under low temperature, low hygroscopic coefficient, and solid resistivity to radioactive rays. The invention also provides novel polyamide acid which is substantially precursor of the thermoplastic polyimide, and also provides novel thermally fusible laminated film for covering conductive wires, featuring solid adhesive property under low temperature, solid resistivity to radioactive rays, and distinct suitability for covering superconductive wires in particular.The novel thermoplastic polyimide is represented by general formula (1) corresponding to the chemical structure shown below; ##STR1## wherein, Ar.sub.1, Ar.sub.2, Ar.sub.4, and Ar.sub.6, respectively designate divalent organic radical, whereas Ar.sub.3 and Ar.sub.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: September 16, 1997
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hiroyuki Furutani, Kazuhisa Danno, Yoshifumi Okamoto, Junya Ida, Yoshihide Oonari, Hitoshi Nojiri, Hirosaku Nagano
  • Patent number: 5631333
    Abstract: Blends compriseA) from 55 to 99% by weight of a matrix of copolyarylene ether sulfones composed ofa.sub.1) from 91 to 97 mol % of structural units ##STR1## a.sub.2) from 3 to 9 mol % of structural units ##STR2## B) from 1 to 45% by weight of a disperse phase comprising copolyarylene ether sulfones, composed ofb.sub.1) from 91 to 97 mol % of structural units II andb.sub.2) from 3 to 9 mol % of structural units I,C) from 0 to 40% by weight of rubber impact modifiers,D) from 0 to 60% by weight of fibrous or particulate fillers or of mixtures thereof andE) from 0 to 40% by weight of processing assistants and/or additives.
    Type: Grant
    Filed: January 10, 1995
    Date of Patent: May 20, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Weber, Gerhard Leiter, J urgen Streib, Eckhard M. Koch
  • Patent number: 5606014
    Abstract: Controlled molecular weight imide oligomers and co-oligomers containing pendent phenylethynyl groups (PEPIs) and endcapped with nonreactive or phenylethynyl groups have been prepared by the cyclodehydration of the precursor amide acid oligomers or co-oligomers containing pendent phenylethynyl groups and endcapped with nonreactive or phenylethynyl groups. The amine terminated amide acid oligomers or co-oligomers are prepared from the reaction of dianhydride(s) with an excess of diamine(s) and diamine containing pendent phenylethynyl groups and subsequently endcapped with a phenylethynyl phthalic anhydride or monofunctional anhydride. The anhydride terminated amide acid oligomers and co-oligomers are prepared from the reaction of diamine(s) and diamine containing pendent phenylethynyl group(s) with an excess of dianhydride(s) and subsequently endcapped with a phenylethynyl amine or monofunctional amine. The polymerizations are carried out in polar aprotic solvents such as under nitrogen at room temperature.
    Type: Grant
    Filed: August 4, 1995
    Date of Patent: February 25, 1997
    Assignee: The United States of America as represented by the United States National Aeronautics and Space Administration
    Inventors: John W. Connell, Joseph G. Smith, Jr., Paul M. Hergenrother
  • Patent number: 5475065
    Abstract: The invention disclosed relates to a process for producing azide-substituted aromatic polymers such as polysulfones, and to certain novel azide-substituted polysulfones so produced. The process involves attaching azide groups onto the aromatic rings of the polymers by first activating the attachment site by direct lithiation or bromination, followed by lithiation. The lithiated intermediates are converted substantially qantitatively to azides by reacting with a suitable azide, preferably tosyl azide, under substantially anhydrous conditions. Novel azide-substituted polysulfones containing from one to about three azide groups per repeat polymer unit were obtained, the degree of azide substitution being determined by the degree of lithiation. The azides may also be converted to other functional derivatives such as primary amines and cross-linked membranes.
    Type: Grant
    Filed: August 22, 1994
    Date of Patent: December 12, 1995
    Assignee: National Research Council of Canada
    Inventors: Michael D. Guiver, Gilles P. Robertson
  • Patent number: 5464923
    Abstract: The present invention provides novel substituted biphenyl pyrazines or pyrazine derivatives ("BPD") which are functional and have useful application as a monomer for a variety of high performance polymers such as polyester, polyarylate, polycarbonate, polyetherketones, epoxides, polyimides, polyamides, and polyamides-imides; and as pigments for coating compositions such as paints. These BPD have the general formula: ##STR1## wherein R.sub.1 -R.sub.8 and n are defined herein.
    Type: Grant
    Filed: October 19, 1994
    Date of Patent: November 7, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: Richard Vicari, George Kvakovszky, Olan S. Fruchey
  • Patent number: 5438082
    Abstract: In order to produce a polymer electrolyte membrane from sulfonated, aromatic polyether ketone, an aromatic polyether ketone of the formula (I) ##STR1## in which Ar is a phenylene ring having p- and/or m-bonds,Ar' is a phenylene, naphthylene, biphenylene, anthrylene or another divalent aromatic unit,X, N and M, independently of one another are 0 or 1,Y is 0, 1, 2 or 3,P is 1, 2, 3 or 4,is sulfonated and the sulfonic acid is isolated. At least 5% of the sulfonic groups in the sulfonic acid are converted into sulfonyl chloride groups, and these are reacted with an amine containing at least one crosslinkable substituent or a further functional group, and unreacted sulfonyl chloride groups are subsequently hydrolyzed. The resultant aromatic sulfonamide is isolated and dissolved in an organic solvent, the solution is converted into a film, and the crosslinkable substituents in the film are then crosslinked.In specific cases, the crosslinkable substituents can be omitted.
    Type: Grant
    Filed: June 10, 1993
    Date of Patent: August 1, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Freddy Helmer-Metzmann, Frank Osan, Arnold Schneller, Helmut Ritter, Konstantin Ledjeff, Roland Nolte, Ralf Thorwirth
  • Patent number: 5362836
    Abstract: Polymer electrolytes are described that comprise a sulfonated aromatic polyether ketone, e.g. of the formula II ##STR1## where A is from 0.2 to 1,c is from 0 to 0.8, anda+c=1.The polymer electrolytes are prepared by dissolving an aromatic polyether ketone in 94-97% by weight sulfuric acid and adding a sulfonating agent, e.g. oleum, to the solution until the sulfuric acid concentration is from 98 to 99.9% by weight.
    Type: Grant
    Filed: June 9, 1993
    Date of Patent: November 8, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Freddy Helmer-Metzmann, Frank Osan
  • Patent number: 5362837
    Abstract: Macrocyclic polyetherimide oligomer compositions are prepared by a displacement reaction at a temperature in the range of about 200.degree.-225.degree. C. between at least one fluorinated aromatic phthalimide and at least one phenolic trialkylsilyl ether compound. Preferably, a bis-fluoroimide and a bis-trialkylsilyl ether of a dihydroxyaromatic compound such as resorcinol are employed. The reaction is conducted by maintaining reagents A and B in high dilution in a dipolar aprotic organic liquid such as N-methylpyrrolidone, and in the presence of a catalytic amount of at least one substantially soluble fluoride. Preferably, a mixture of reagents A and B is added to solvent containing the catalyst.
    Type: Grant
    Filed: July 26, 1993
    Date of Patent: November 8, 1994
    Assignee: General Electric Company
    Inventors: Tohru Takekoshi, Jane M. Terry
  • Patent number: 5304626
    Abstract: A chemical resistant copolymer useful in electronic applications, said copolymer is a polyimide containing a 3,3',4,4'-tetracarboxybiphenyl dianhydride (BPDA) moiety, at least one other dianhydride moiety, and at least one diamine.
    Type: Grant
    Filed: September 13, 1991
    Date of Patent: April 19, 1994
    Assignee: Amoco Corporation
    Inventors: Marvin J. Burgess, Douglas E. Fjare, Herbert J. Neuhaus
  • Patent number: 5290906
    Abstract: A poly(arylene ether ketone) of this invention principally comprises recurring units represented by formula ##STR1## wherein Ar.sup.1 denotes a 1,5-naphthalene ring, a 2,6-naphthalene ring, a 2,7-naphthalene ring or a combination of them, and Ar.sup.2 denotes p-phenylene, p,p'-biphenylene, a 1,5-naphthalene ring, a 2,6-naphthalene ring, a 2,7-naphthalene ring or a combination of them.The poly(arylene ether ketone) is high in second-order transition temperature and excellent in solvent resistance and moldability, and can be molded into heat-resistant fibers and electric insulating films.
    Type: Grant
    Filed: January 23, 1991
    Date of Patent: March 1, 1994
    Assignee: Teijin Limited
    Inventors: Shunichi Matsumura, Seiji Itoh, Hiroo Inata, Jiro Sadanobu
  • Patent number: 5264538
    Abstract: Cyclic poly(aryl ether) oligomers and mixtures thereof, and methods for the preparation thereof in a highly dilute reaction medium under reaction conditions favorable for ring closure at low degrees of polymerization. These oligomers are represented by the general formula ##STR1## where each Y is divalent oxygen or divalent sulfur, each Ar is an aromatic diradical which comprises one or more C.sub.6 to C.sub.20 arylene groups and has at least one electron withdrawing group attached to an aromatic ring, and n is an integer from 1 to about 20 with the proviso that for integer values of n equal to 1 or 2 all linkages between independent aromatic rings comprise at least one atom.
    Type: Grant
    Filed: June 27, 1990
    Date of Patent: November 23, 1993
    Assignee: The Dow Chemical Company
    Inventors: Michael J. Mullins, Edmund P. Woo, Kimberly E. Balon, Daniel J. Murray, Cheng-Cheng C. Chen
  • Patent number: 5239043
    Abstract: An improved process for the preparation of poly(aryl ether) polymers by reacting, in the absence of dipolar aprotic solvents, an alkali metal double salt of a dihydric phenol with a dihalobenzenoid compound in the presence of a macro bicyclic compound having nitrogen bridgehead atoms linked together by three hydrocarbon bridging chains having in each of the hydrocarbon bridging chains at least one additional hetro atom selected from the group consisting of oxygen, nitrogen and sulfur atoms.The poly(aryl ether) polymer resins produced by the process have a low degree of coloration and excellent mechanical and electrical properties which allow them to be molded into a variety of articles.
    Type: Grant
    Filed: December 31, 1991
    Date of Patent: August 24, 1993
    Assignee: Amoco Corporation
    Inventor: Selvaraj Savariar
  • Patent number: 5235019
    Abstract: An improved process for the preparation of poly(aryl ether) polymers by reacting, in the absence of dipolar aprotic solvents, an alkali metal double salt of a dihydric phenol with a dihalobenzenoid compound in the presence of a macrocyclic polyether compound having one ether ring in which oxygen atoms are separated one from the other by 2 to 3 carbon atoms, the ring having fused thereto from 0 to 4 monocyclic or polycyclic aromatic or saturated hydrocarbon nuclei. The nuclei are attached by vicinal carbon atoms thereof to adjoining ring oxygens in oxygen-carbon-carbon-oxygen arrangement.The poly(aryl ether) polymer resins produced by the process have a low degree of coloration and excellent mechanical and electrical properties which allow them to be molded into a variety of articles.
    Type: Grant
    Filed: December 31, 1991
    Date of Patent: August 10, 1993
    Assignee: Amoco Corporation
    Inventor: Selvaraj Savariar
  • Patent number: 5235020
    Abstract: An improved process for the preparation of poly(aryl ether) polymers by reacting, in the absence of dipolar aprotic solvents, an alkali metal double salt of a dihydric phenol with a dihalobenzenoid compound in the presence of an alkoxylated tertiary amine compound having a nitrogen atom linking together three organic chains comprising hydrocarbon groups and in each of the chains at least one oxygen atom.The poly(aryl ether) polymer resins produced by the process have a low degree of coloration and excellent mechanical and electrical properties which allow them to be molded into a variety of articles.
    Type: Grant
    Filed: December 31, 1991
    Date of Patent: August 10, 1993
    Assignee: Amoco Corporation
    Inventor: Selvaraj Savariar
  • Patent number: 5229482
    Abstract: Aromatic polyether polymers, illustrated by polyethersulfones, polyetherketones and polyetherimides, are prepared by a phase transfer catalyzed reaction between a salt of a dihydroxyaromatic compound and a substituted aromatic compound such as bis(4-hydroxyphenyl) sulfone, bis(4-hydroxyphenyl) ketone or 1,3-bis[N-(4-chlorophthalimido)]benzene or the corresponding derivative of toluene or diphenyl ether, or the analagous fluoro-, bromo- or nitro-substituted compounds. The phase transfer catalysts employed are those which are stable at temperatures in the range of about 125.degree.-250.degree. C. Particularly preferred phase transfer catalysts are the hexaalkylguanidinium and .alpha.,.omega.-bis(pentaalkylguanidinium)alkane salts and the corresponding heterocyclic salts.
    Type: Grant
    Filed: February 28, 1991
    Date of Patent: July 20, 1993
    Assignee: General Electric Company
    Inventor: Daniel J. Brunelle
  • Patent number: 5227455
    Abstract: Premix for the production of mouldings, containingA) from 40-99.95% by weight of polymer granules A based on a polyaryl ether sulfone, polyaryl ether ketone, polyimide, polyamide imide or polyether imide, or a mixture thereof,B) up to 50% by weight of fillers B in fiber or particle form, or a mixture thereof,C) from 0.05-10% by weight of a compound C ether of the general formula X ##STR1## where A1 to A7 are identical or different and, independently of one another, are a radical of the formula --CO--, --O--, --S--, --SO.sub.2 --, --C(CH.sub.3).sub.2 --, a chemical bond, ##STR2## and k, l, m, n, p and q are each 0 or 1, or a C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy or cyano derivative thereof which is substituted on the aromatic ring, or of the general formula Y ##STR3## where R is C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy or cyano, A8 to A11 are as defined for A1 to A7, r, s and t are 0 or 1, and x is 2, 3 or 4, or a mixture thereof,is described.
    Type: Grant
    Filed: September 4, 1992
    Date of Patent: July 13, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Ittemann, Gerhard Heinz
  • Patent number: 5221727
    Abstract: The new aromatic polyethers containing ester groups, which are distinguished by high dimensional stability, may be used for the production of all kinds of moulded products as well as for the preparation of block copolymers of aromatic polyether segments and segments of other thermoplastic polymers.
    Type: Grant
    Filed: February 25, 1991
    Date of Patent: June 22, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Robert Kumpf, Rolf Wehrmann, Harald Pielartzik, Dittmar Nerger
  • Patent number: 5216117
    Abstract: The solvent-resistance and thermal stability of polyamideimides of the general formulae: ##STR1## is improved by capping the amideimides with a crosslinking functionality (Y) containing a residue selected from the group of: ##STR2## wherein R.sub.1 =lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl (either including hydroxyl or halo-substituents), halogen, or mixtures thereof;j= 0, 1, or 2;G=--CH.sub.2 --, --O--, --S--, --SO.sub.2 --, --SO--, --CO--, --CHR--, or --CR.sub.2 --;R=hydrogen, lower alkyl, or phenyl;T=methallyl or allyl;Me=methyl;R.sub.2 =a trivalent organic radical; andR.sub.3 =a divalent organic radical.The amideimide oligomers may be linear or multidimensional, and can be processed into blends, prepregs, or composites. Methods of making these amideimides and intermediates useful in the syntheses are also described.
    Type: Grant
    Filed: January 13, 1992
    Date of Patent: June 1, 1993
    Assignee: The Boeing Company
    Inventors: Clyde H. Sheppard, Hyman R. Lubowitz
  • Patent number: 5212264
    Abstract: There are disclosed substantially linear polyarylene ether sulfones having a reduced viscosity of having a reduced viscosity of ca. 0.25 to ca. 1.5 dl/g (measured in a 1% solution in DMF at 25.degree. C.) and consisting essentially of 95-99.8% by weight of segments of formula I and of 5-0.2% by weight of segments of formula IIa, formula IIb and/or formula IIc ##STR1## the percentages by weight being based on the entire polymer and the molecular weight (number average) of the segments of formula I being 6000 to ca. 60 000, if the polymer contains solely structural units of formula IIa and/or IIb, and 1000 to ca. 60 000 if the polymer contains more than 0.1% by weight of structural units of formula IIc, and R consists of the recurring structural units of formula Ia and/or of up to 99.8% by weight, based on the total polymer, of recurring structural units of formula Ib ##STR2## wherein R.sub.1 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.10 alkenyl, phenyl or halogen, p is an integer from 0 to 4 Ar.sub.1 and Ar.
    Type: Grant
    Filed: March 16, 1992
    Date of Patent: May 18, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Kurt Hoffmann, Thomas Kainmuller, Rudolf Pfaendner
  • Patent number: 5212278
    Abstract: The invention relates to polyarylene ethers which contain, based on the total amount of structural elements present in the polyether resin, 5-100 mol % of a recurring structural element of the formula I ##STR1## and 0-95 mol % of a recurring structural element of the formula II ##STR2## in which X and X' independently of one another are --SO--, --SO.sub.2 -- or --CO--, one of the radicals R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is phenyl or phenyl which is substituted by one to three (C.sub.1 -C.sub.4)alkyl groups and the remaining radicals R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently of one another are hydrogen, (C.sub.1 -C.sub.4)alkyl, phenyl or phenyl which is substituted by one to three (C.sub.1 -C.sub.4)alkyl groups, and A is an aromatic radical, at least 25% of the bonds X and/or Y and/or the bridge members contained in A being --SO.sub.2 --.These industrial materials are distinguished by very good mechanical properties and good solubility.
    Type: Grant
    Filed: March 13, 1990
    Date of Patent: May 18, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Rudolf Pfaendner, Thomas Kainmuller, Kurt Hoffmann, Andreas Kramer, Friedrich Stockinger
  • Patent number: 5204442
    Abstract: Polyether polymers are prepared from 4,4"-dihydroxy-m-terphenyls, especially the unsubstituted dihydroxyterphenyl, by reaction under alkaline conditions with bis(4-halophenyl) sulfones, 4,4'-dihalobenzophenones or gem-dihaloalkanes. Both homopolymers and copolymers with other dihydroxyaromatic compounds, particularly bisphenol A, may be prepared. They have glass transition temperatures higher than those of the corresponding bisphenol A-derived polymers.
    Type: Grant
    Filed: February 6, 1991
    Date of Patent: April 20, 1993
    Assignee: General Electric Company
    Inventor: Susan A. Nye
  • Patent number: 5198525
    Abstract: Aromatic polyether sulfones based on 5 to 90 mol-%, based on total bisphenols, of special dihydroxydiphenyl cycloalkanes and 10 to 95 mol-% based on the bisphenols of specific phthaleins, a process for their production and their use as molding compounds.
    Type: Grant
    Filed: May 21, 1990
    Date of Patent: March 30, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Knud Reuter, Wolfgang Jilge, Bernd Pittel, Gunther Weymans
  • Patent number: 5194561
    Abstract: Process for the preparation of an aromatic polyether in the presence of finely divided condensation auxiliaries.The process for the preparation of an aromatic polyether by condensation of the reactants in the presence of carbonates of metals of Group I of the Periodic Table, as condensation auxiliaries, employs the metal carbonates sodium carbonate or sodium bicarbonate or mixtures thereof in the form of very finely ground salts.The fine particle size distribution of the carbonate allows a significant shortening of the reaction times and permits polyethers having a defined degree of condensation to be reproducibly prepared.
    Type: Grant
    Filed: August 7, 1990
    Date of Patent: March 16, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Fischer, Arnold Schneller
  • Patent number: 5189137
    Abstract: A method for preparing high molecular weight polyethermide polymers in a dual solvent system is disclosed. The inventive method provides for polymerizing a diamine monomer and a dianhydride monomer in a solvent system comprised of at least two solvents, a first solvent is selected for its solubility characteristics such that the polyethermide polymer is highly soluble therein and a second solvent is selected for its relatively high boiling point characteristics such that when the second solvent and first solvent are mixed together, the boiling point of the dual solvent system is at least as high as the temperature at which polymerization of said monomers occurs. In one embodiment, a diamine monomer of 4,4'-sulfonyl dianiline (SDAN) is reacted with a dianhydride monomer of bisphenol A dianhydride (BPADA) in the presence of a catalyst and a chain stopper in a dual solvent system comprised of chloroform and ortho-dichlorobenzene. The resulting polyethermide has an intrinsic viscosity exceeding 0.
    Type: Grant
    Filed: October 7, 1991
    Date of Patent: February 23, 1993
    Assignee: General Electric Company
    Inventors: Paul E. Howson, Patricia D. Mackenzie
  • Patent number: 5175242
    Abstract: A new class of soluble phenylated polyimides made from 3,6-diarypyromellitic dianhydride and process for the manufacture of the 3,6-diarypyromellitic dianhydride starting material. The polyimides obtained with said dianhydride are readily soluble in appropriate organic solvents and are distinguished by excellent thermal, electrical and/or mechanical properties making the polyimides ideally suited as coating materials for microelectronic apparatii, as membranes for selective molecular separation or permeation or selective gas separation or permeation, or as reinforcing fibers in molecular composites, or as high modulus, high tensile strength fibers.
    Type: Grant
    Filed: February 24, 1989
    Date of Patent: December 29, 1992
    Assignee: The University of Akron
    Inventor: Frank W. Harris
  • Patent number: 5175234
    Abstract: Polyimide oligomers include (1) linear, monofunctional crosslinking oligomers prepared by condensing a monoanhydride end cap with a diamine that includes alternating ether and "Sulfone" (--SO.sub.2 --, --S--, --CO--, --(CF.sub.3).sub.2 C--, or --(CH.sub.3).sub.2 C--) linkages connecting alternating aromatic radicals and with a dianhydride (or dianhydride mixture), particularly the unsaturated, aliphatic dianhydride commonly known as MCTC; (2) linear, mono- or difunctional crosslinking oligomers prepared by condensing an amine end cap with a diamine and a dianhydride; and (3) multidimensional, crosslinking oligomers having an aromatic hub and at least three radiating arms connected to the hub, each arm including a crosslinking end cap at its distal end and at least one imide linkage.Blends, prepregs, and composites can be prepared from the oligomers.
    Type: Grant
    Filed: November 7, 1989
    Date of Patent: December 29, 1992
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 5169907
    Abstract: A block copolymer represented by the formula ##STR1## are formed by contracting an ester group containing poly(aryl ether) composed of the recurring units ##STR2## with a polyarylcarbonate composed of the recurring units ##STR3## in which B, Z, E.sup.5, E.sup.1, E.sup.2 x, y, n and p represent specified groups or valuesunder conditions such that ester/carbonate interchange reactions will occur.
    Type: Grant
    Filed: November 14, 1990
    Date of Patent: December 8, 1992
    Assignee: Miles Inc.
    Inventors: Robert J. Kumpf, Dittmar K. Nerger, Rolf Wehrmann, Harald Pielartzik
  • Patent number: 5166305
    Abstract: Novel aromatic polysulfoneetherketone polymers having recurring units of Formula: ##STR1## wherein Ar is phenylene, biphenylene or ##STR2## in which --Y-- represents ##STR3## The aromatic polysulfoneetherketone polymers of the invention have superior properties over the known polysulfone or polyetherketone series polymers in terms of heat resistance, chemical resistance and electric insulation as well as mechanical properties such as dimensional stability.
    Type: Grant
    Filed: January 4, 1991
    Date of Patent: November 24, 1992
    Assignee: Korea Institute of Science and Technology
    Inventors: Jong W. Park, In T. Lee
  • Patent number: 5166306
    Abstract: Flame-resistant thermoplastic branched polycarbonates of high molecular weight are prepared from:(1) a carbonate precursor;(2) at least one dihydroxyaromatic compound of formula: ##STR1## where: R is a single bond, or a substituted or non-substituted linear or branched C.sub.1 -C.sub.5 alkylene radical, or a group chosen from O, S, SO.sub.2 and CO;X and Y, which may be the same or different, are H or CH.sub.3 ;m and n, which may be the same or different, are whole numbers from 1 to 4;(3) at least one halogenated pyrimidine compound of formula: ##STR2## where: R.sub.2, R.sub.3, R.sub.4, which may be the same or different, are chlorine or bromine or hydrogen, on condition that at least one is chlorine or bromine;R.sub.1 is chlorine or bromine, or a radical of formula: ##STR3## where Z is NH or S or O; (4) at least one polyfunctional organic compound as branching agent, characterized by possessing at least three equal or different groups chosen from the groups OH, COOH, COCl and SO.sub.2 Cl.
    Type: Grant
    Filed: December 27, 1991
    Date of Patent: November 24, 1992
    Assignee: Enichem Technoresine S.p.A.
    Inventor: Alberto Petri
  • Patent number: 5144001
    Abstract: Described herein are amorphous thermoplastic terpolymers containing units of the formula: ##STR1## wherein R is independently hydrogen, C.sub.1 to C.sub.6 alkyl, or C.sub.4 to C.sub.8 cycloalkyl, a is an integer of 0 to 4 and n is independently an integer of 1 to 3. The units are attached to each other by an --0-- bond. These polymers have an excellent combination of mechanical properties. They display high notched izod impact values, high heat distortion temperatures and excellent environmental stress crack resistance.
    Type: Grant
    Filed: January 19, 1990
    Date of Patent: September 1, 1992
    Assignee: Amoco Corporation
    Inventor: Louis M. Maresca
  • Patent number: 5144000
    Abstract: Polyetherimide oligomers having crosslinking end cap moieties which provide improved solvent-resistance to cured composites are generally represented by the formula: ##STR1## wherein X=--O-- or --S--; ##STR2## n=1 or 2; ##STR3## E=allyl or methallyl; R=a trivalent C.sub.(6-13) aromatic organic radical;R.sub.1 =any of lower alkyl, lower alkoxy, aryl, or substituted aryl;R'=a divalent C.sub.(6-30) aromatic organic radical;j=0, 1, or 2; andG=--CH.sub.2 --, --O--, --S--, or --SO.sub.2 --The crosslinkable oligomers are made by reacting substituted phthalic anhydrides with hydroxyaryl amines and suitable crosslinking end cap reactants, or by self-condensation of phthalimide salts followed by capping the polymers.
    Type: Grant
    Filed: July 9, 1990
    Date of Patent: September 1, 1992
    Assignee: The Boeing Company
    Inventors: Clyde H. Sheppard, Hyman R. Lubowitz
  • Patent number: 5126427
    Abstract: Polyarylene ether sulfones which have a reduced viscosity of 0.1 to 2.0 dl/g, measured at 25.degree. C. in a 1% solution in N-methylpyrrolidone (NMP), and which contain, based on the total number of structural units present in the polyarylene ether sulfone resin, 99-1 mol % of a recurring structural unit of formula I ##STR1## and 1-99 mol % of a recurring structural unit of formula II--O--Ar.sub.2 --O--Ar.sub.1 -- (II)wherein the aromatic rings in the structural unit of formula I are unsubstituted or substituted by one or more C.sub.1 -C.sub.4 alkyl groups, C.sub.1 -C.sub.4 alkoxy groups or halogen atoms, Ar.sub.1 is a radical of formula IIIa-IIIc ##STR2## wherein a is 0 or 1, ##STR3## which radical is unsubstituted or substituted by one or more C.sub.1 -C.sub.4 alkyl groups, C.sub.1 -C.sub.4 alkoxy groups or halogen atoms, and Ar.sub.2 is a radical of formula IVa-IVe ##STR4## wherein b is 0 or 1 ##STR5## wherein c is 0 or 1 ##STR6## wherein Z is --CO--, --SO.sub.
    Type: Grant
    Filed: March 6, 1991
    Date of Patent: June 30, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Rudolf Pfaendner, Thomas Kainmuller, Kurt Hoffmann, Friedrich Stockinger, Andreas Kramer
  • Patent number: 5118766
    Abstract: A process for making a polymer carrying a plurality of pendant groups SO.sub.2 Z' (where Z' is halogen) comprises reacting with an inorganic acid halide a substantially water-insoluble derivative of the corresponding polymer sulphonic acid with cations of valency 2, 3 or 4. The process is especially useful when the polymer sulphonic acid is one which in free acid form or monovalent cation salt form is soluble in or heavily swollen by water at temperatures in the range 0.degree.-30.degree. C. Suitably the polymer sulphonic acid is derived from a polyarylether-sulphone or -ketone or -sulphone/-ketone copolymer containing dioxyphenylene groups.
    Type: Grant
    Filed: July 24, 1989
    Date of Patent: June 2, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Brian N. Hendy, Stella M. Young
  • Patent number: 5116933
    Abstract: A crystalline polyarylether capable of being shaped into fibers or films or moulded or used as a matrix in composites, contains repeating units Ph'.sub.n, Ar.sup.1 and Ar.sup.2 connected by ether linkages, whereinPh' is 1,3 or 1,4-phenylene optionally substituted with 0 to 4 methyl or chloro groups,n is an integer from 1 to 4Ar.sup.1 is Ph[CO[Ph'CO].sub.x Ph].sub.ywhereinx=0 or 1y=1 or 2Ph is 1,4-phenylene optionally substituted with 0 to 4 methyl or chloro groups, andAr.sup.2 is [Ph.sub.n SO.sub.2 ].sub.v Ph'.sub.wwherein u, v and w are integers from 1 to 4; said units being in the relative molar proportions:______________________________________ Ph'.sub.n 40 to 60% Ar.sup.1 92 to 50% of the total of Ar1 and Ar.sup.2. and Ar.sup.
    Type: Grant
    Filed: December 4, 1989
    Date of Patent: May 26, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventor: Alan B. Newton
  • Patent number: 5112942
    Abstract: Copolyimides and their precursors are disclosed comprising units represented by the formula ##STR1## where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are the same or different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, with the proviso that R.sub.1, R.sub.2, R.sub.3 and R.sub.4 cannot simultaneously be hydrogen and where Z is a chemical bond, ##STR2## Ar is the tetravalent residue of a tetracarboxylic acid or acid dianhydride or di- or tetraester thereof, where x and y are integers from about 100 to about 1,000, and the ratio of x to y is from about 1:99 to about 49:51, and z is 0-5.These copolymers have improved resistance to stress cracking. They may also be used in applications such as coatings, or adhesives.
    Type: Grant
    Filed: September 26, 1990
    Date of Patent: May 12, 1992
    Assignee: Ethyl Corporation
    Inventor: Wesley C. Blocker
  • Patent number: 5104967
    Abstract: The solvent-resistance and thermal stability of polyamideimides of the general formulae: ##STR1## is improved by capping the amideimides with a crosslinking functionality (Y) containing a residue selected from the group of: ##STR2## wherein R.sub.1 =lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl (either including hydroxyl or halo-substituents), halogen, or mixtures thereof;j=0, 1, or 2;G=--CH.sub.2 --, --O--, --S--, --SO.sub.2 --, --SO--, --CO--, --CHR--, or --CR.sub.2 --;R=hydrogen, lower alkyl, or phenyl;T=methallyl or allyl;Me=methyl;R.sub.2 =a trivalent organic radical; andR.sub.3 =a divalent organic radical.The amideimide oligomers may be linear or multidimensional, and can be processed into blends, prepregs, or composites. Methods of making these amideimides and intermediates useful in the syntheses are also described.
    Type: Grant
    Filed: April 13, 1988
    Date of Patent: April 14, 1992
    Assignee: The Boeing Company
    Inventors: Clyde H. Sheppard, Hyman R. Lubowitz
  • Patent number: 5101006
    Abstract: Novel halogenated polyimides and co-polyimides comprise recurring imide structural units of the formula ##STR1## where X is F, Cl, Br or I; Y is H, F, Cl, Br or I; and R is a divalent organic radical.
    Type: Grant
    Filed: March 25, 1991
    Date of Patent: March 31, 1992
    Assignee: Occidental Chemical Corporation
    Inventors: Jeffrey S. Stults, Willis T. Schwartz
  • Patent number: 5075412
    Abstract: Aromatic polymers comprise divalent aromatic units connected by ether and/or thioether linkages. At least one of such units carries at least one halogen radical linked to a nuclear carbon by a halogen-carbon bond or a functionalized derivative thereof linked to a nuclear carbon atom by a carbon-carbon bond.
    Type: Grant
    Filed: December 12, 1989
    Date of Patent: December 24, 1991
    Assignee: Imperial Chemical Industries plc
    Inventors: Patrick T. McGrail, Paul D. MacKenzie, Ian W. Parsons
  • Patent number: 5066409
    Abstract: Disclosed is an aryl ether sulfone of the following formula: ##STR1## wherein R.sup.1 is independently in each occurrence hydrogen, alkyl, alkoxy, aryl, aryloxy, polyhaloaryl, polyhaloaryloxy, polyhaloalkylaryl, or polyhaloalkylaryloxy, R.sup.2 is independently in each occurrence hydrogen, alkyl, alkoxy, aryl, aryloxy, polyhaloaryl, polyhaloaryloxy, polyhaloalkylaryl, or polyhaloalkylaryloxy, and n is a whole number from 1 to 5. Also disclosed is a lubricant composition which comprises a lubricating fluid and an aryl ether sulfone as shown above, wherein the aryl ether sulfone is present in an amount sufficient to increase the lubricity of the lubricating fluid component.
    Type: Grant
    Filed: September 12, 1990
    Date of Patent: November 19, 1991
    Assignee: The Dow Chemical Company
    Inventor: Bassam S. Nader
  • Patent number: 5053477
    Abstract: The present invention relates to a process for the production of high molecular weight crystalline aromatic polyether ketones from an aromatic dihydroxy compound and an aromatic dihalogeno compound which contains a keto group, characterized in that N-C1-C5 alkyl caprolactam solvents and a mixture of alkali metal compounds consisting of at least one alkali metal carbonate and at least one compound selected from alkali metal hydroxides, bicarbonates, fluorides, hydrides, alkoxides (e.g. methylates or ethylates) and alkylates (e.g. ethyls or butyls) are used.
    Type: Grant
    Filed: February 26, 1990
    Date of Patent: October 1, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Sabine Kern, Joachim Genz, Frank Kleiner, Volker Eckhardt, Karsten J. Idel
  • Patent number: 5053478
    Abstract: Production of polyenaminonitriles including those which can be cyclized to very stable poly(aminoquinolines) without the evolution of any small molecules and thus in a manner free of volatiles. The polyenaminonitriles are polymers which have desirable dielectric properties, and include those which can be cyclized to poly(aminoquinolines) without the evolution of volatiles to make defect-free films and composites of similar dielectric properties because of this characteristic.
    Type: Grant
    Filed: August 2, 1990
    Date of Patent: October 1, 1991
    Inventors: James A. Moore, Douglas Robello
  • Patent number: 5049642
    Abstract: Sulphonated polyarylethers or thioethers are formed by polycondensing difunctional monomers having phenolic and/or thiophenolic and/or halogenic end groups in the presence of a dipolar aprotic solvent, at least to one of which monomers a sulphonic acid or a sulphonate salt is attached. The monomer(s) which the sulphonate group is attached is selected from monomers of formula I:X--Ph.sub.n --Y Iwherein:Ph is phenylene;X and Y are independently --OH or --SH; andn is an integer selected from 1 to 3.
    Type: Grant
    Filed: December 21, 1989
    Date of Patent: September 17, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventor: Brian N. Hendy
  • Patent number: 4966954
    Abstract: Production of polyenaminonitriles including those which can be cyclized to very stable poly(aminoquinolines) without the evolution of any small molecules and thus in a manner free of volatiles. The polyenaminonitriles are polymers which have desirable dielectric properties, and include those which can be cyclized to poly(aminoquinolines) without the evolution of volatiles to make defect-free films and composites of similar dielectric properties because of this characteristic.
    Type: Grant
    Filed: May 23, 1988
    Date of Patent: October 30, 1990
    Assignee: Rensselaer Polytechnic Institute
    Inventors: James A. Moore, Douglas Robello
  • Patent number: 4960851
    Abstract: A crystalline polyethersulphone comprises repeating units Ph SO.sub.2 Ph.sub.3 SO.sub.2 Ph alone or together with Ph.sub.n and optionally together with up to 20 mole % of other repeating units, said units being connected by ether linkages, and wherein Ph is 1,4 - phenylene and n is an integer 1 or 2.
    Type: Grant
    Filed: February 27, 1989
    Date of Patent: October 2, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventor: Philip A. Staniland