Nitrogen-containing Reactant Contains An Amine Group Patents (Class 528/229)
  • Patent number: 5194576
    Abstract: Aromatic polyamides with an improved stability toward thermal oxidation was achieved by polycondensation being performed in the presence of 0.05 to 4 mol % of a catalyst comprising a mixture of phosphorus compounds and metal salts.With the process according to the invention, it is possible to obtain aromatic polyamides stable toward thermal oxidation.
    Type: Grant
    Filed: January 31, 1992
    Date of Patent: March 16, 1993
    Assignee: Huels Aktiengesellschaft
    Inventors: Gunter Poll, Jurgen Finke, Horst Heuer
  • Patent number: 5177179
    Abstract: Perfluoroalkylated diaminoesitylene and polymers, preferably polyimides, made therefrom. The necessarily obtainable meta-substitution position of the perfluoroalkyl group with respect to both amino-groups provides an improved diamine and compositions of matter resulting therefrom.
    Type: Grant
    Filed: April 4, 1991
    Date of Patent: January 5, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Brian C. Auman, David P. Higley, Bruce B. Johnson
  • Patent number: 5177181
    Abstract: Disclosed is an aromatic diamine having the general formula ##STR1## where A is a group containing at least one aromatic ring, each Y is independently selected from ##STR2## R is a group containing at least one olefinically unsaturated group, R' is hydrogen, alkyl to C.sub.25, aryl, or R, n is 1 to 4, and the number of olefinic groups in Y is at least 3 when each Y is ##STR3## and otherwise is at least 2. Photosensitive polyamic acids and polyimides can be prepared from the aromatic diamines which can be crosslinked with light to a mask to form patterns on a substrate.
    Type: Grant
    Filed: June 6, 1991
    Date of Patent: January 5, 1993
    Assignee: Occidental Chemical Corporation
    Inventors: Jerold Rosenfeld, Jin-O Choi, David Y. Tang, John Tyrell
  • Patent number: 5177176
    Abstract: Polyimide compositions, films, and electronic devices using polyimides, based on 9-aryl-9(perfluoroalkyl)-xanthene-2,3,6,7-dianhydride and one or more diamines from a selected group, which offers to the polyimides a combination of desirable properties including solubility, pseudo rod-like structure, low linear coefficient of thermal expansion, high glass transition temperature, low dielectric constant, and high modulus.
    Type: Grant
    Filed: October 29, 1991
    Date of Patent: January 5, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Brian C. Auman
  • Patent number: 5177180
    Abstract: Polyimide intercondensation products are prepared from mixed dianhydrides and aromatic diamines. One of the mixed dianhydrides must be 2,2-bis(3,4-dicarboxyphenyl)-hexafluoropropane dianhydride (6FDA) and the other dianhydride may be oxydiphthalic anhydride (ODPA) or biphenyl dianhydride (BPDA) or mixtures thereof. Preferred aromatic diamines are p-phenylenediamine (PPD) and/or m-phenylenediamine (MPD). The polyimide products have increased glass transition temperatures (Tg), frequently higher than 400.degree. C. Composites made from the polyimides have high thermal and oxidative stability and may be used in aircraft engine hardware.
    Type: Grant
    Filed: August 7, 1990
    Date of Patent: January 5, 1993
    Assignee: General Electric Company
    Inventors: Richard N. Griffin, Robert A. Gray
  • 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: 5175240
    Abstract: Aromatic homopolyimide and copolyimide films derived from an aromatic dianhydride and a chlorinated aromatic diamine such as 2-chloro-p-phenylene diamine and 2,2'-dichloro-4,4'-diaminodiphenyl ether are described. The films have low water absorption, high elastic modulus and elongation and can be heat-processed without embrittlement.
    Type: Grant
    Filed: December 17, 1990
    Date of Patent: December 29, 1992
    Assignee: E.I. Du Pont de Nemours and Company
    Inventors: John A. Kreuz, Stuart N. Milligan
  • Patent number: 5175241
    Abstract: Polyimide resins, which have reduced anhydride content when molded, are prepared by a novel reaction process that includes reacting an esterified aromatic tetracarboxylic acid or anhydride monomer with a primary aromatic diamine until substantially no free monomer remains to form a polyamide-acid (the molar ratio of esterified monomer to diamine ranging from 1:1 to 1:2); reacting the polyamide-acid with a low molecular weight end-capping agent to form an end-capped polyamide-acid; and heating the end-capped polyamide-acid to form the polyimide.
    Type: Grant
    Filed: December 28, 1989
    Date of Patent: December 29, 1992
    Assignee: The Dexter Corporation
    Inventor: David S. Darrow
  • 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: 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: 5171822
    Abstract: An improved low toxicity polymerization of monomer reactants (PMR) system has 3,4'-oxydianiline as the key monomer reactant. One variation of this system, LaRC-RP46, is prepared by reacting together monomethyl ester or 5-norbornene-2,3-dicarboxylic acid (NE), 3,4'-oxydianiline (3,4'-ODA), and dimethyl ester of 3,3',4,4'-benzophenonetetracarboxylic acid (BTDE); this combination is then treated with heat. This new matrix resin is readily processed into a high quality graphite fiber reinforced composite with excellent reproducibility. The flexibility of the ether linkage in 3,4'-ODA provides high toughness. The composite retains excellent mechanical properties both at 316.degree. C. and at 371.degree. C. The development of LaRC-RP46 will significantly extend the applications of PMR type polyimides.
    Type: Grant
    Filed: February 5, 1991
    Date of Patent: December 15, 1992
    Assignee: The United States of America as represented by the Administrator of National Aeronautics and Space Administration
    Inventor: Ruth H. Pater
  • Patent number: 5171828
    Abstract: Polyimide copolymers are disclosed having the recurring structure ##STR1## wherein AR is AR.sub.1 or AR.sub.2, wherein AR.sub.1 is ##STR2## and wherein AR.sub.2 is ##STR3## provided that the molar ratio of AR.sub.1 to AR.sub.2 is 3:1 to 1:3, and wherein AR.sub.3 is ##STR4## These polyimides have unexpected properties which are useful in various electronic applications.
    Type: Grant
    Filed: August 5, 1991
    Date of Patent: December 15, 1992
    Assignee: Occidental Chemical Corporation
    Inventors: Timothy A. Meterko, Rudolph F. Mundhenke, Willis T. Schwartz
  • Patent number: 5171829
    Abstract: A copolymeric amphiphilic polyimide precursor having the recurring unit of the formula (1): ##STR1## wherein R.sup.1 is a tetravalent group having at least 2 carbon atoms, R.sup.2 is a bivalent group having at least 2 carbon atoms, and R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are hydrogen atom or a monovalent group having 1 to 30 carbon atoms selected from the group consisting of an aliphatic group, an alicyclic group, an aromatic group, a group in which an aliphatic group is combined with an aromatic group, or an alicyclic group, and their groups substituted by a halogen atom, nitro group, amino group, cyano group, methoxy group or acetoxyl group, provided that at least one of R.sup.3, R.sup.4, R.sup.5 and R.sup.6 is neither hydrogen atom nor the above-mentioned group which has 1 to 11 carbon atoms; a part of at least one of said R.sup.1 and said R.sup.2 being substituted with a group having a valence different therefrom.
    Type: Grant
    Filed: January 16, 1991
    Date of Patent: December 15, 1992
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Masakazu Uekita, Hiroshi Awaji
  • Patent number: 5166308
    Abstract: Disclosed is an aromatic copolyimide film prepared by chemical conversion of a copolyamide acid solution obtained by copolymerization of an aromatic tetracarboxylic acid component comprising from 30 to 50 mole % of biphenyltetracarboxylic acid dianhydride, 50 to 70 mole % of pyromellitic acid dianhydride, 60 to 80 mole % of p-phenylenediamine and 20 to 40 mole % of 4,4'-diaminodiphenyl ether. The aromatic copolyimide film has a low coefficient of thermal expansion, low water absorption, a low coefficient of hygroscopic expansion, high mechanical strength and is readily etchable making it suitable for use an advanced electronic substrate.
    Type: Grant
    Filed: April 30, 1990
    Date of Patent: November 24, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: John A. Kreuz, Richard F. Sutton, Jr.
  • 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: 5162492
    Abstract: Polyimide prepared from 3,3'4,4'-biphenyltetracarboxylic dianhydride and an aromatic diamine which is at least about 60% meta-phenylene diamine exhibits excellent hydrolytic and oxidative stability.
    Type: Grant
    Filed: October 11, 1990
    Date of Patent: November 10, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Mureo Kaku
  • 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: 5159048
    Abstract: The invention is concerned with an isocyanate-reactive composition comprising a polymer having a molecular weight of at least 500 containing a plurality of groups of the formula: ##STR1## wherein R.sup.1 represents hydrogen or a hydrocarbon radical;R.sup.2 represents a hydrocarbon radical;R.sup.3 represents an organic radical carrying at least one isocyanate-reactive group, andR.sup.4 represents hydrogen or an optionally substituted hydrocarbon radical. Such compositions are useful for making moulded elastomers and flexible foams.
    Type: Grant
    Filed: October 10, 1990
    Date of Patent: October 27, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Edward F. Cassidy, Malcolm Hannaby
  • Patent number: 5159055
    Abstract: The physical properties of high performance composites can be tailored by using coreactive oligomer blends to make the composites. The blends include a first oligomer having an unsaturated hydrocarbon end cap and a second oligomer having an amine, hydroxyl, sulfhydryl, or ##STR1## functionality. Upon curing, the oligomers homopolymerize (i.e. addition polymerize) and mutually interlink (i.e. copolymerize) to form composites possessing intermediate properties to those exhibited by the pure oligomers. The coreactive oligomer blends may also include noncrosslinking polymers and other coreactants, as desired. Stiffness or toughness can be increased in thermally stable composites without significant loss of other properties through these coreactive oligomer blends that cure to block copolymers.
    Type: Grant
    Filed: March 3, 1992
    Date of Patent: October 27, 1992
    Assignee: The Boeing Company
    Inventors: Clyde H. Sheppard, Hyman R. Lubowitz
  • Patent number: 5157107
    Abstract: A polymeric acid is synthesized by the ring-opening poly-addition reaction using a biphenyl tetracarboxylic acid as a tetracarboxylic acid moiety and an aromatic diamine, particularly p-phenylene diamine, as a diamine moiety. An aromatic polyimide resin layer possessing a highly desirable heat-resisting property as a heat-resistant insulating coating material and excelling in adhesive strength relative to a substrate is obtained by adjusting the polymeric acid in viscosity with a suitable organic solvent, applying the resultant polyamic acid on a substrate, and firing the applied layer of the polyamic acid. The substrate, for example, is a conductor layer formed as with copper and used as a multi-layer wiring board for hybrid IC's.
    Type: Grant
    Filed: August 29, 1989
    Date of Patent: October 20, 1992
    Assignees: Kabushiki Kaisha Toshiba, Toshiba Chemical Corporation
    Inventors: Masaru Nikaido, Hikaru Okunoyama, Katsumi Yanagibashi, Yoshiaki Ouchi
  • Patent number: 5155206
    Abstract: The thermooxidative stability and thermomechanical properties of advanced composites which use high performance resin matrices such as polyimides and high strength carbon fibers may be improved by sizing the carbon fibers with uncapped or capped linear polyamideimides.The uncapped linear polyamideimides useful as carbon fiber sizings generally contain repeating units having the general formula: ##STR1## wherein R.sub.2 =a trivalent organic radical and generally benzenetriyl;R.sub.3 =a divalent organic radical; andn=an integer sufficiently large to provide a strong, tough coating.Useful capped, linear polyamideimide oligomers may be formed by including end caps with an unsaturated functionality (Y) containing a residue selected from the group consisting of: ##STR2## wherein R.sub.1 =lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl, halogen, or mixtures thereof;j=0, 1, or 2;i=1 or 2;G=--CH.sub.2 --, --O--, --S--, --SO.sub.2 --, --SO--, --CO--, --CHR--, or --CR.sub.
    Type: Grant
    Filed: April 28, 1989
    Date of Patent: October 13, 1992
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard, Ronald R. Stephenson
  • Patent number: 5153304
    Abstract: The present invention relates to a novel fluorine-containing diaminobenzene derivative having a perfluoroalkyl group and to a novel fluorine-containing polyimide which is produced from the said diaminobenzene as a starting material and to a novel polyimide having both a fluorine-containing group and/or a siloxane chain in the side chain thereof, the polyimide being produced from the said fluorine-containing diaminobenzene and fluorine-containing polyimide and to a liquid crystal-aligning agent with an elevated tilt angle, which contains a polyimide having a fluorine-containing group and a siloxane chain.
    Type: Grant
    Filed: March 18, 1992
    Date of Patent: October 6, 1992
    Assignees: Sagami Chemical Research Center, Nissan Chemical Industries, Ltd.
    Inventors: Yu Nagase, Yuriko Takamura, Noriaki Kohtoh, Hiroyoshi Fukuro, Toyohiko Abe
  • Patent number: 5149761
    Abstract: The new aromatic ether imides corresponding to the following formula ##STR1## may be used for the production of plastics which in turn may be worked up into moulded articles, films, sheet products and filaments. The plastics produced from the new aromatic ether imides are distinguished by their exceptional dimensional stability under heat.
    Type: Grant
    Filed: November 1, 1990
    Date of Patent: September 22, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Knud Reuter, Dieter Freitag, Gunther Weymans, Rolf Dhein
  • Patent number: 5149755
    Abstract: A method for the preparation of poly(benzoxazole)s, poly(benzimidazoles)s, and poly(benzthiazole)s. In the presence of solvent and catalyst, reacting carbon monoxide, an aromatic halide reactant having the general formula X.sup.1 --Ar.sup.1 --Z.sup.1 and an aromatic amine reactant having the general formula Z.sup.2 --Ar.sup.2 --M.sup.1, wherein X.sup.1 and Z.sup.1 are non-ortho, Z.sup.2 and M.sup.1 are non-ortho, one of Z.sup.1 and Z.sup.2 is X.sup.2 and the other one is M.sup.2, --Ar.sup.1 -- and --Ar.sup.2 -- are each independently selected from the group consisting of aromatic and heteroaromatic moieties having a total of ring carbons and heteroatoms of from 6 to about 20, X.sup.1 and X.sup.2 are each independently selected from the group consisting of --I and --Br, and M.sup.1 and M.sup.2 are each independently selected from moieties having an --NH.sub.2 radical and, ortho to the --NH.sub.2 radical, a radical selected from the group consisting of --NH.sub.2, --OH, and --SH.
    Type: Grant
    Filed: July 5, 1991
    Date of Patent: September 22, 1992
    Assignee: Eastman Kodak Company
    Inventor: Robert J. Perry
  • Patent number: 5149762
    Abstract: A silicon-modified thermoplastic resin is prepared by heating a mixture comprised of 10 to 90% by weight of an imide group-containing thermoplastic resin and 90 to 10% by weight of a modified silicon compound having an amino group--NH.sub.2 at one end of the molecule and an alkyl group --C.sub.n H.sub.2n+1 (n is an integer of at least 1) at the other end of the molecule, to chemically bond the imide group-containing thermoplastic resin to the modified silicon compound.
    Type: Grant
    Filed: November 8, 1989
    Date of Patent: September 22, 1992
    Assignee: Mitsubishi Rayon Company Ltd.
    Inventors: Yoshio Murashige, Junko Soga
  • Patent number: 5147966
    Abstract: The invention is a novel polyimide prepared from 3,4'-oxydianiline (3,4'-ODA) and 4,4'-oxydiphthalic anhydride (ODPA), in 2-methoxyethyl ether (diglyme). The polymer has been prepared in ultra high molecular weight and in a controlled molecular weight form which has a 2.5 percent offset is stoichiometry (excess diamine) with a 5.0 percent level of phthalic anhydride as an endcap. This controlled molecular weight form allows for greatly improved processing of the polymer for moldings, adhesive bonding, and composite fabrication. The higher molecular weight version affords tougher films and coatings. The overall polymer structure groups in the dianhydride, the diamine, and a metal linkage in the diamine affords adequate flow properties for making this polymer useful as a molding powder, adhesive, and matrix resin.
    Type: Grant
    Filed: July 31, 1990
    Date of Patent: September 15, 1992
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Terry L. St. Clair, Donald J. Progar
  • Patent number: 5147925
    Abstract: A polyurethane polymer having desired chain-pendant or in-chain groups Y is prepared by 1) converting terminal isocyanate groups of an isocyanate-terminated polyurethane prepolymer to groups providing carbon- or nitrogen-bound --NH.sub.2 and/or --NH-- groups, and 2) chain extending modified prepolymer formed in 1) with a compound having at least two enolic carbonyl groups and also having at least one group Y which becomes chain-pendant or in-chain in the chain-extended polymer.
    Type: Grant
    Filed: February 14, 1991
    Date of Patent: September 15, 1992
    Assignees: Imperial Chemical Industries PLC, ICI Resins BV
    Inventors: David A. Pears, Martinus P. J. Heuts
  • Patent number: 5145937
    Abstract: New polyimides have been prepared from the reaction of aromatic dianhydrides with novel aromatic diamines containing carbonyl and ether connecting groups between the aromatic rings. Several of these polyimides were shown to be semi-crystalline as evidenced by wide angle x-ray diffraction and differential scanning calorimetry. Most of the polyimides form tough solvent resistant films with high tensile properties. Several of these materials can be thermally processed to form solvent and base resistant moldings.
    Type: Grant
    Filed: November 9, 1989
    Date of Patent: September 8, 1992
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Paul M. Hergenrother, Stephen J. Havens
  • Patent number: 5145940
    Abstract: Mixtures of salts of organic dicarboxylic acids and organic compounds of non-salt character, dissolved in a C.sub.1 -C.sub.4 alkanol, can be concentrated or separated with a semipermeable membrane made from a copolyimide which contains a first aromatic diamine radical (1) and a second aromatic diamine radical (2) which carries --SO.sub.3 M groups, wherein M is H.sym., a mono- to trivalent metal cation or an ammonium cation. The first amine radical (1) and/or the second diamine radical (2) contains C.sub.1 -C.sub.4 alkyl groups in both o-positions to at least one amino group. These copolyamides are also radiation-sensitive (self-crosslinking) and can be used for the production of protective layers or relief images, development being carried out in an aqueous alkaline medium.
    Type: Grant
    Filed: August 12, 1991
    Date of Patent: September 8, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Wolfgang Wernet, Joseph Berger
  • Patent number: 5145943
    Abstract: Fusible polyimide powders are prepared by the process of this invention. An amic acid amine is first prepared by treating (n+1) moles of a bis(aminophenyl)methane with n mole of aromatic tetracarboxylic anhdride to produce an aromatic amic acid prepolymer. This prepolymer is then mixed with an unsaturated carbocyclic monoanhydride and the mixture heated to form a reactive end-capped polyamic acid precursor. The resulting composition is thermally treated in order to partially imidize the precursor. The resulting fusible polyimide powder is finally separated.
    Type: Grant
    Filed: December 17, 1990
    Date of Patent: September 8, 1992
    Assignee: Ethyl Corporation
    Inventors: Hsueh M. Li, John Y. Lee
  • Patent number: 5140095
    Abstract: This invention relates to a biodegradable polyamide. In particular, this invention relates to a polyamide containing keto carbonyl groups set out in monomeric units along the main chain of the polymer and having structure (I), wherein n and m are equal or different whole numbers ranging from 8 to 10, preferably 8. Said polyamides are high light-sensitive to the solar U.V. radiation, so that the exposure of the products obtained by means of such polyamides to the U.V. solar radiation causes the product to be transformed into a fragile or friable material, that is biodegradable.
    Type: Grant
    Filed: January 31, 1991
    Date of Patent: August 18, 1992
    Assignee: SNIA Tecnopolimeri S.p.A.
    Inventors: Cesare Guaita, Gianluigi Semeghini
  • Patent number: 5132394
    Abstract: Composites comprising polyamide-imide matrix resins derived from trimellitic acid compounds and an aromatic diamine are improved in moisture resistance when from 10 to about 90 mole % of the trimellitic acid compounds are replaced by biphenyl tetracarboxylic acid compounds.
    Type: Grant
    Filed: August 24, 1989
    Date of Patent: July 21, 1992
    Assignee: Amoco Corporation
    Inventor: Ronald E. Bockrath
  • 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: 5128440
    Abstract: Aromatic copolyamides are described, which are soluble in organic amide solvents. The polymers are composed to at least 95 mol % of repeat structural unitsA: --OC--AR--CO--B: --HN--Ar'--NH--C: --HN--Ar"--NH-- ##STR1## in the combinations A+B+C+D, or A+C+D+E and up to 5 mol % of m-bond-containing structural units F and/or G derived from aromatic dicarboxylic acids (F') and/or from aromatic diamines (G'), the sum total of the mole fractions of structural units A+F and the sum total of the mole fractions of the structural units of B+C+D+E+G being essentially the same, --Ar-- and --Ar'-- are divalent aromatic radicals whose C--N valence bonds are in a para-position or in a similar coaxial or parallel position and which may be substituted by one or two inert radicals, such as lower alkykl or halogen, ##STR2## is a trivalent aromatic radical which after removal of the --SO.sub.2 R group has the same meaning as --Ar-- or --Ar'-- or else is the structural unit ##STR3## wehre X is --O--, --NHCO--, --SO.sub.
    Type: Grant
    Filed: February 13, 1991
    Date of Patent: July 7, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Keil, Reiner Hess, Jochen Rapp
  • Patent number: 5120826
    Abstract: The present invention provides for a novel heat stable class of polyamide-imide polymers having excellent flow properties and hydrolytic stability which are prepared by forming the polycondensation product of one or more aromatic or aliphatic diamines and a comonomer comprising a tri- or hexafluoro-substituted tricarboxylic acid anhydride (or acid derivative thereof) having the structure: ##STR1## wherein R is CF.sub.3 or a phenyl radical. In addition to improved flow properties, the polyamide-imide polymers of this invention also exhibit improved solubility properties in most organic solvents, good resistance to attack by chlorinated solvents such as trichloroethylene as compared with polyimides, improved hydrophobic properties as well as good thermal properties, including resistance to thermooxidative degradation.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: June 9, 1992
    Assignee: Hoechst Celanese Corp.
    Inventors: Rohitkumar H. Vora, Paul N. Chen, Sr.
  • Patent number: 5120825
    Abstract: The present invention provides for hybrid polybenzimidazole and polybenzimidazolone polymers which are characterized as containing both imidazole and imidazolone structural units in the polymer chain. These polymers are characterized as containing at least one recurring monomer unit containing the structure of the formula: ##STR1## wherein Ar is a tetravalent aromatic moiety derived from an aromatic tetraamine and Ar.sub.1 is a trivalent aromatic moiety derived from a trifunctional acid, an acid anhydride or amine-reactive derivatives thereof, said polymers further characterized by an inherent viscosity of at least about 0.01 dl/g measured as a 0.5% solution in N-methyl pyrrolidone at 25.degree. C.The polymers of this invention exhibit many of the advantageous properties of both polybenzimidazole and polybenzimidazolone polymers. They are characterized as being extremely resistant to chemical attack such as by solvents, acids and bases.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: June 9, 1992
    Assignee: Hoechst Celanese Corp.
    Inventors: Rohitkumar H. Vora, Paul N. Chen, Sr.
  • Patent number: 5120814
    Abstract: To produce flame-retardant thermostable new homopolyimides having structural units of the general formula ##STR1## by reacting 3,3',4,4'-benzophenone tetracarboxylic acid dianhydride with an overall equimolar amount of 2,4- and/or 2,6-toluene diisocyanate, the reaction is carried out in the presence of a polymerization accelerator. The new homopolyimides have a glass transition point of at least 320.degree. C. and are processible to moulded articles exhibiting a similarly good structural strength as could hitherto be observed in mixed polyimides only. Furthermore, the new homopolyimides can be spun to fibres.
    Type: Grant
    Filed: January 31, 1990
    Date of Patent: June 9, 1992
    Assignee: Lenzing AG
    Inventors: Sigrid Seidl, Klaus Weinrotter, Herbert Griesser
  • Patent number: 5116935
    Abstract: A preferred class of polyimide oligomers include (1) linear, difunctional crosslinking oligomers prepared by condensing an imidophenylamine end cap with a lower alkylene diamine or a polyaryldiamine such as 3,3'-phenoxyphenylsulfone diamine and with a dianhydride, particularly 4,4'-phenoxyphenylsulfone dianhydride; and (2) multidimensional, crosslinking, polyimide oligomers having an aromatic hub and at least two radiating arms connected to the hub, each arm including a crosslinking imidophenylamine end cap at its distal end and at least two imide linkages.Blends, prepregs, and composites can be prepared from the oligomers.
    Type: Grant
    Filed: May 18, 1989
    Date of Patent: May 26, 1992
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • 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: 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: 5112934
    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: November 27, 1989
    Date of Patent: May 12, 1992
    Assignee: The Dow Chemical Company
    Inventors: John J. Kester, H. Craig Silvis
  • Patent number: 5112941
    Abstract: An aromatic polyimide separation membrane prepared by subjecting an aromatic polyimide membrane to fluorine treatment with an active fluorine is described. The aromatic polyimide separation membrane according to the present invention has an extremely high selectivity and gas permeability, and therefore, is useful as a membrane for separation of gas mixtures or liquid mixtures.
    Type: Grant
    Filed: June 27, 1990
    Date of Patent: May 12, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Tetsuo Kasai, Yoshiteru Kobayashi
  • 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: 5104962
    Abstract: Disclosed is a thermosetting resin composition which comprises a specific bismaleimide compound or polymaleimide and a specific aromatic diamine compound. It can be widely used for electrical and electronic parts, various structural parts, sliding parts and the like.
    Type: Grant
    Filed: October 23, 1990
    Date of Patent: April 14, 1992
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Norimasa Yamaya, Masahiro Ohta, Akihiro Yamaguchi
  • Patent number: 5104966
    Abstract: Novel polyimide based films are disclosed that are resistant to arc tracking and that include aromatic dianhydrides together with aromatic diamines and aliphatic diamines. The compositions contain from 5 to 20 percent by weight of the aliphatic diamine. These compositions maximize the thermal aging capability of the polyimide. The compositions are useful as films and laminates for wire and cable.
    Type: Grant
    Filed: June 13, 1989
    Date of Patent: April 14, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Harris B. David
  • Patent number: 5102982
    Abstract: Aromatic polyamides of the invention are polyamides comprising a recurring unit ##STR1## and a recurring unit [--NH--Ar.sub.1 --NH--] and copolyamides comprising a recurring unit ##STR2## and a recurring unit [--NH--Ar.sub.2 --NHCO--Ar.sub.3 --CO--] wherein Ar.sub.1 and Ar.sub.2 are, for example, phenylene group, naphthylene group, biphenylene group, and 4,4'-methylenediphenylene group and Ar.sub.3 is, for example, phenylene group, naphthylene group and biphenylene group in which both the bonding chains extend in the coaxial direction or in the parallel direction to axis.The aromatic polyamide of the invention has high glass transition temperature and has heat resistance, high strength, and high elasticity and besides is soluble in various solvents and is excellent in spinnability and film-formability. The aromatic polyamide is molded into fibers or films and can be utilized as electric insulating materials, laminates, varnishes, fabrics, synthetic papers, etc.
    Type: Grant
    Filed: October 1, 1990
    Date of Patent: April 7, 1992
    Assignee: Showa Shell Sekiyu Kabushiki Kaisha
    Inventor: Shunichi Koide
  • Patent number: 5102959
    Abstract: The present invention relates to copolyimides of 100-70 mol % of recurring structural units of the formula I and 0-30 mol % of recurring structural units of the formula II ##STR1## in which z.sup.a is a tetravalent aromatic tetracarboxylic acid radical other than that of thioxanthonetetracarboxylic acid, the carboxyl groups thereof in each case being located in pairs in the ortho-position or peri-position relative to one another, and x.sup.a is a divalent aromatic diamine radical which, in at least one ortho-position relative to at least one nitrogen atom, carries a hydrocarbon substituent having at least one aliphatic .alpha.-hydrogen atom or x.sup.a is a radical of the formula III ##STR2## in which X.sup.c is a divalent aromatic diamine radical which, in ortho-position relative to both nitrogen atoms, carries in each case at least one mono-valent hydrocarbon substituent having at least one aliphatic .alpha.-hydrogen atom, n assumes an average value of 1.0 to 2.5, Z.sup.b is as defined for Z.sup.a and X.sup.
    Type: Grant
    Filed: March 2, 1990
    Date of Patent: April 7, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Ottmar Rohde, Stanley J. Jasne, Josef Pfeifer
  • Patent number: 5101005
    Abstract: The present invention provides cross-linkable polyimide polymers having at least one repeating unit of the sturcture of: ##STR1## wherein n is the number of repeating groups and A is a tetravalent aromatic organic radical wherein each pair of carbonyl groups are attached to adjacent carbons in the ring moiety A.It has been found that polyimides having the structure of formula I may be crosslinked at surprisingly low temperatures when heated from about 75 to about 110.degree. C. to form infusible and solvent resistant shapes, thereby rendering them useful in the preparation of films, laminates and composites where inertness to solvents is a prerequisite.
    Type: Grant
    Filed: May 18, 1989
    Date of Patent: March 31, 1992
    Assignee: Hoechst Celanese Corp.
    Inventors: Rohitkumar H. Vora, Dinesh N. Khanna, Wolfgang K. Appel
  • 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: 5098990
    Abstract: A new process for making polyesters, polyamides and polyketones which comprises reacting a dihydric alcohol, a diamine or a diacylaromatic compound with a bis(trichloromethylketone) compound and in the presence of a basic catalyst, as necessary.
    Type: Grant
    Filed: September 23, 1987
    Date of Patent: March 24, 1992
    Assignee: The Dow Chemical Company
    Inventor: Marlin E. Walters