From Carboxylic Acid Having Three Or More Carboxylic Acid Groups Or Derivatives Thereof, And An Organic Amine, Or From An Organic Amine Salt Of A Tri-or Higher Carboxylic Acid Patents (Class 528/350)
  • Patent number: 5493000
    Abstract: This invention relates to a branched fractal three dimensional porous polymer species which comprises rigid aromatic recurring units having electrophilic or nucleophilic reactive moieties on the exterior thereof. Another aspect of this invention relates to a star polymer comprising a polymeric core formed of the fractal polymers (FPS) of this invention having linear polymeric moieties grafted to the exterior thereof by way of residues formed by reaction between the reactive moieties on the exterior of the fractal polymer (FP) and complimentary reactive moieties on a linear polymer. Yet another aspect of this invention relates to polymeric composites comprising a polymer matrix having dispersed therein the star polymers of this invention.
    Type: Grant
    Filed: August 23, 1993
    Date of Patent: February 20, 1996
    Assignee: AlliedSignal Inc.
    Inventor: Shaul M. Aharoni
  • Patent number: 5489644
    Abstract: Solutions of polyimide-forming substances containA) aromatic or partly aromatic diamines andB) tetraesters of imide-forming aromatic or partly aromatic tetracarboxylic acids or mixtures of these tetraesters with the corresponding tri-, di- and/or monoesters.These solutions are suitable for the production of coatings.
    Type: Grant
    Filed: March 31, 1994
    Date of Patent: February 6, 1996
    Assignee: BASF Lacke + Farben
    Inventors: Rainer Blum, Gerhard Hoffmann
  • Patent number: 5484879
    Abstract: Polyimide polymers of the following recurring structure and the corresponding polyamic acids are disclosed: ##STR1## wherein AR.sub.1 is ##STR2## where X is O, S, SO, SO.sub.2, CO, C(CF.sub.3).sub.2, C(CH.sub.3).sub.2, Si(CH.sub.3).sub.2, or a single bond, wherein AR.sub.2 may be pyromellitic dianhydride, a substituted pyromellitic dianhydride, naphthanoic dianhydride, or ##STR3## where Y is O, S, SO, SO.sub.2, CO, C(CF.sub.3).sub.2, C(CH.sub.3).sub.2, Si(CH.sub.3).sub.2 --O--AR--O--, or a single bond, where AR is an aromatic nucleus.
    Type: Grant
    Filed: December 17, 1990
    Date of Patent: January 16, 1996
    Assignee: Occidental Chemical Corporation
    Inventors: Robert A. Buchanan, Jeffrey S. Stults, Ronald F. Spohn
  • Patent number: 5480965
    Abstract: This invention relates to a novel thermoplastic and amorphous polyimide which is readily soluble in organic solvent, a novel aromatic diamino compound used for the polyimide, a preparation process thereof, a polyimide-based resin composition comprising the thermoplastic polyimide and a fibrous reinforcement, a process for preparing the resin composition, an injection molded article of the resin composition, a polyimide-based composite obtained by molding the above soluble and thermoplastic polyimide in combination with a fibrous reinforcement, and a fibrous reinforcement having a surface modified with the above polyimide.
    Type: Grant
    Filed: July 26, 1994
    Date of Patent: January 2, 1996
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Wataru Yamashita, Yuichi Okawa, Hideaki Oikawa, Tadashi Asanuma, Yuko Ishihara, Mitsunori Matsuo, Keizaburo Yamaguchi, Akihiro Yamaguchi, Shoji Tamai
  • Patent number: 5480964
    Abstract: A negative birefringent film, useful in liquid crystal displays, and a method for controlling the negative birefringence of a polyimide film is disclosed which allows the matching of an application to a targeted amount of birefringence by controlling the degree of in-plane orientation of the polyimide by the selection of functional groups within both the diamine and dianhydride segments of the polyimide which affect the polyimide backbone chain rigidity, linearity, and symmetry. The higher the rigidity, linearity and symmetry of the polyimide backbone, the larger the value of the negative birefringence of the polyimide film.
    Type: Grant
    Filed: April 21, 1994
    Date of Patent: January 2, 1996
    Assignee: The University of Akron
    Inventors: Frank W. Harris, Stephen Z. D. Cheng
  • Patent number: 5480963
    Abstract: Bioabsorbable copolymers are derived from tricarboxylic acids and triols. The copolymers are useful in forming surgical articles including, sutures, suture coatings, and gels for promoting tissue repair.
    Type: Grant
    Filed: July 22, 1994
    Date of Patent: January 2, 1996
    Assignee: United States Surgical Corporation
    Inventors: Ying Jiang, John S. Bobo, Elliott A. Gruskin
  • Patent number: 5478913
    Abstract: Copolyimides from 1,4-bis(4-aminophenoxy)-2-phenylbenzene and m- or p-phenylene diamine with biphenyl dianhydride exhibit a high Tg and reduced melt viscosity.
    Type: Grant
    Filed: August 31, 1994
    Date of Patent: December 26, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Richard J. Boyce, Thomas P. Gannett, James M. Sonnett, Murty S. Tanikella, Brian C. Auman
  • Patent number: 5478916
    Abstract: A solvent resistant copolyimide was prepared by reacting 4,4'-oxydiphthalic anhydride with a diaimine blend comprising, based on the total amount of the diamine blend, about 75 to 90 mole percent of 3,4'-oxydianiline and about 10 to 25 mole percent p-phenylene diamine. The solvent resistant copolyimide had a higher glass transition temperature when cured at 350.degree. , 371.degree. and 400.degree. C. than LaRC.TM.-IA. The composite prepared from the copolyimide had similar mechanical properties to LaRC.TM.-IA. Films prepared from the copolyimide were resistant to immediate breakage when exposed to solvents such as dimethylacetamide and chloroform. The adhesive properties of the copolyimide were maintained even after testing at 23.degree., 150.degree., 177.degree. and 204.degree. C.
    Type: Grant
    Filed: September 1, 1994
    Date of Patent: December 26, 1995
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Alice C. Chang, Terry L. St. Clair
  • Patent number: 5478917
    Abstract: Solutions of polyimide-forming substances containA) aromatic or partly aromatic polyamines andB) amides or a mixture of esters and amides of tetracarboxylic acids.Solutions are useful as coating compositions.
    Type: Grant
    Filed: October 11, 1994
    Date of Patent: December 26, 1995
    Assignee: BASF Lacke + Farben Aktiengesellschaft
    Inventors: Rainer Blum, Gerhard Hoffmann
  • Patent number: 5478914
    Abstract: Polyimides comprising recurring units of the following general formula (1) ##STR1## wherein R.sub.1 represents a tetravalent aromatic group. Polyimide copolymers and preparations of the polyimides and the polyimide copolymers are also described.
    Type: Grant
    Filed: July 1, 1994
    Date of Patent: December 26, 1995
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Ichiro Kaneko, Atushi Sugitani, Masahiro Yuyama, Kiyoshi Motomi
  • Patent number: 5478915
    Abstract: Polyimide oligomers are described which comprise the condensation product of: at least one phenylindane diamine and at least one aromatic bis(ether anhydride). The polyimide oligomers of the invention are readily processed to form solution prepregable polyimide composites having high glass transition temperatures and high temperature and oxidative stability. More particularly, the present invention provides for crosslinkable polyimide oligomers prepared by reacting, in a suitable solvent under an inert atmosphere, a mixture of monomers comprising: (A) an aromatic diamine component comprising from about 25 to 100 mole % of at least one phenylindane diamine; (B) a dianhydride component comprising from about 25 to 100 mole % of at least one aromatic his(ether anhydride); and (C) at least one end-cap monomer selected from the group consisting of monoanhydrides, acyl halides and aromatic amines, wherein each end-cap monomer contains at least one crosslinkable functional group in the molecule.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: December 26, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Michael Amone, Mark R. Southcott
  • Patent number: 5473010
    Abstract: The present invention relates to a polyimide based resin composition comprises 1 to 50 parts by weight of polyetherimide for 100 parts by weight a resin composition comprising 50 to 99 parts by weight of polyarylether ketone and 50 to 1 parts by weight of polyimide having specific structural units.The polyimide based resin compositions have excellent fatigue characteristics and creep resistance and are expected widely to apply in field of machine and automobile parts which is required permanence for mechanical strength.
    Type: Grant
    Filed: August 30, 1994
    Date of Patent: December 5, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Atsushi Morita, Tomohito Koba, Toshiaki Takahashi, Katsunori Shimamura, Toshiyuki Kataoka, Hiroyuki Furukawa, Hiroaki Tomimoto
  • Patent number: 5464928
    Abstract: The invention is a direct process for preparing semi-crystalline polyimides. This process comprises the steps of: providing a polar aprotic solvent, adding a dianhydride and a diamine to the solvent to form a mixture, stirring the mixture at ambient temperature, and adding glacial acetic acid to the mixture to provide a ratio of polar aprotic solvent to glacial acetic acid which ranges from about 90 to 10 to about 75 to 25 by volume to form a solution. The solution was heated to a range from about 110.degree. C. to about 140.degree. C. to form a polyimide precipitate. The polyimide precipitate was recovered as a semi-crystalline polyimide powder.
    Type: Grant
    Filed: September 1, 1994
    Date of Patent: November 7, 1995
    Assignee: The United States of America as represented by the United States National Aeronautics and Space Administration
    Inventors: Alice C. Chang, Terry L. St. Clair
  • Patent number: 5464925
    Abstract: The present invention is an oligomer represented by the formula: ##STR1## wherein X is a moiety selected from the group consisting of: ##STR2## where each Y is independently S, O, CH.sub.2, C.dbd.O, CH.sub.3 --C--CH.sub.3, O.dbd.S.dbd.O, or CF.sub.3 --C--CF.sub.3.In another aspect, the present invention is a polymer of the above-described oligomer.
    Type: Grant
    Filed: May 25, 1994
    Date of Patent: November 7, 1995
    Assignee: The Dow Chemical Company
    Inventors: Eric S. Moyer, Denise J. D. Moyer
  • Patent number: 5464927
    Abstract: Copolyamic acid is obtained from tetracarboxylic acid dianhydride, diamine and a fluorinated diamine and/or fluorinated tetracarboxylic acid dianhydride; and optionally ester or amine salt derivative thereof to obtain radiation sensitive polymer; and low optical high thermally stable polyimide from curing the above polyamic acid and/or derivative thereof.
    Type: Grant
    Filed: May 10, 1993
    Date of Patent: November 7, 1995
    Assignee: International Business Machines Corporation
    Inventors: Marie Angelopoulos, Jeffrey D. Gelorme, Jeffrey W. Labadie, David A. Lewis, Sally A. Swanson, Nancy C. Labianca
  • Patent number: 5463016
    Abstract: This invention provides (1) a granular material of a polyimide precursor, which has excellent solubility in solvents and excellent moldability and from which a polyimide molding having excellent mechanical properties can be produced, (2) a mixture of a granular material of a polyimide precursor with a solvent, in which the polyimide precursor shows excellent storage stability and (3) a process for the production of a granular material of a polyimide precursor, in which a solvent can be easily removed. Particularly provided are a polyimide precursor granular material having an intrinsic viscosity of 0.7 or higher and a polyimide precursor mixture which consists of a polyimide precursor granular polyimide having an intrinsic viscosity of 0.7 or higher and a solvent that does not exhibit a strong-mutual interaction with the polyimide precursor, as well as a process for the production of the polyimide precursor granular material.
    Type: Grant
    Filed: February 9, 1994
    Date of Patent: October 31, 1995
    Assignee: Unitika Ltd.
    Inventors: Isao Tomioka, Takeshi Nakano, Mikio Furukawa, Yoshiaki Echigo
  • Patent number: 5461099
    Abstract: A polyimide varnish which is a solution having a polyimide and/or a polyimide precursor dissolved in an organic solvent and which is useful for forming a polyimide coating film on a substrate by coating the solution on the substrate followed by heat treatment, wherein from 5 wt % to 60 wt % of the organic solvent is a lactic acid derivative of the formula (I): ##STR1## wherein each of R.sup.1 and R.sup.2 which are independent of each other, is hydrogen, a C.sub.1-5 alkyl group or a C.sub.1-5 alkenyl group.
    Type: Grant
    Filed: December 23, 1994
    Date of Patent: October 24, 1995
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Motoaki Ishikawa, Makoto Mishina, Yoshihiro Tsuruoka
  • Patent number: 5459232
    Abstract: A nonlinear optical material composed of a polyimide obtained from a diamine and/or a diacid anhydride or dithioacid anhydride substituted by a portion having a nonlinear optical effect or of molecules having a benzocyclobutene structure substituted at the portions having an nonlinear linear optical effect.
    Type: Grant
    Filed: July 9, 1993
    Date of Patent: October 17, 1995
    Assignee: Fujitsu Limited
    Inventors: Wataru Sotoyama, Satoshi Tatsuura, Tetsuzo Yoshimura, Azuma Matsuura, Tomoaki Hayano
  • Patent number: 5459233
    Abstract: In one aspect, the present invention relates to polyimides having excellent thermal resistance and process for preparing the same comprising carrying out condensation of 4,4'-bis(3-aminophenoxy)biphenyl with pyromellitic dianhydride in the presence of a different diamine compound and optionally with a different tetracarboxylic acid dianhydride.In a second aspect, the present invention relates to a heat resistant resin composition consisting essentially of an aromatic polyetherimide and a defined polyimide.In a third aspect, the present invention relates to a polyimide resin composition comprised on a defined polyimide and a separate high-temperature engineering polymer.In a fourth aspect, the present invention relates to a resin composition comprised of a defined polyimide and an aromatic polyamideimide.
    Type: Grant
    Filed: December 7, 1993
    Date of Patent: October 17, 1995
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Shoji Tamai, Masahiro Ohta, Saburo Kawashima, Katsuaki Iiyama, Hideaki Oikawa, Akihiro Yamaguchi
  • Patent number: 5458127
    Abstract: Novel compounds having use as contrast agents in magnetic resonance imaging, as well as other uses, are described. The compounds are comprised of a copolymer which comprises at least two of a first monomer of the formula X.sub.1 --(CHR.sub.2 CHR.sub.2 -Y).sub.n -(CHR.sub.2).sub.m --CHR.sub.2 CHR.sub.2 13 X.sub.2, wherein X.sub.1 and X.sub.2 are, independently, OH, NH.sub.2, NHR.sub.1, COOH, COOR.sub.1, SH, or Z, Y is O, NH, NR.sub.1, S, or CO, n is 0-10,000, m is 0 or 1, each Z is, independently, Cl, Br, or I, each R.sub.1 is, independently, a C.sub.1 -C.sub.20 substituted alkyl or cycloalkyl, and each R.sub.2 is, independently, H or OH, and at least one of a second monomer which is a polynitrilo chelating agent having at least two COOH, COOR.sub.1, or COZ groups, the first and second monomers being bound to one another to form a copolymer through an ester, amide, or carboxylic thioester linkage of at least one of the OH, NH.sub.2, NHR.sub.1, COOH, COOR.sub.
    Type: Grant
    Filed: September 13, 1994
    Date of Patent: October 17, 1995
    Assignee: ImaR.sub.x Pharmaceutical Corp.
    Inventors: Evan C. Unger, Guanli Wu
  • Patent number: 5457154
    Abstract: A moldable polyimide resin composition which has melt-flowability and excellent processability in addition to essential heat-resistant of polyimide and comprises an aromatic bisimide compound and polyimide resin. A further aspect relates to a carbon fiber reinforced polyimide resin composition which has excellent mechanical strengths and comprises a carbon fiber coated with aromatic bisimide compound on the surface and the polyimide resin. A still further aspect relates to a novel bisimide compound which is very useful as the aromatic bisimide compound in the composition.
    Type: Grant
    Filed: November 9, 1992
    Date of Patent: October 10, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Masahiro Ohta, Akio Matsuyama, Eiji Senoue, Fumiaki Kuwano, Osamu Yasui, Yasunori Yoshida, Akinori Ryu, Tadashi Kobayashi
  • Patent number: 5455327
    Abstract: Two monomers containing meta-biphenylenedioxy moieties were prepared. One monomer, a diamine, is used to prepare polyimide, polyamide, and epoxy polymers. The other monomer, a dianhydride, was used to prepare polyimide polymers. These polymers are used to make films, coatings, and selective membranes.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: October 3, 1995
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Terry L. St. Clair, J. Richard Pratt
  • Patent number: 5453484
    Abstract: A diamine compound of the general formula ##STR1## wherein the arrows denote isomerism, R.sub.1 is a divalent aromatic group selected from the group consisting of ##STR2## R.sub.2 is a tetravalent aromatic group selected from the group consisting of ##STR3## and R.sub.4 is a monovalent aliphatic group selected from the group consisting of ethyl and isopropyl; and, a process for preparing same.
    Type: Grant
    Filed: June 30, 1994
    Date of Patent: September 26, 1995
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Suh Bong Rhee, Ji Young Chang, Bong Seok Moon, Ji-Woong Park
  • Patent number: 5449741
    Abstract: A polyimide optical material, composed of a perfluorinated polyimide having a perfluorinated repeating unit represented by general formula (1) ##STR1## wherein R.sub.1 is a tetravalent perfluorinated organic group; and R.sub.2 is a divalent perfluorinated organic group.
    Type: Grant
    Filed: October 25, 1993
    Date of Patent: September 12, 1995
    Assignee: Nippon Telegraph and Telephone Corporation
    Inventors: Shinji Ando, Toru Matsuura, Shigekuni Sasaki, Fumio Yamamoto
  • Patent number: 5449742
    Abstract: Polyimide optical waveguide structures comprising a core within a cladding wherein at least one of the core and the cladding is a polyimide containing 6FDA, BTDA, an aromatic diamine having bulky methyl groups ortho to the amine, and a co-diamine wherein the polyimides have the properties of low optical loss, low optical absorbance, controllable refractive index, and high thermal stability, and wherein the polyimides are photosensitive and solvent resistant.
    Type: Grant
    Filed: February 15, 1994
    Date of Patent: September 12, 1995
    Assignee: Amoco Corporation
    Inventors: Allyson J. Beuhler, David A. Wargowski
  • Patent number: 5442030
    Abstract: Polyimides are made from the novel diamines 1,2-bis(3-aminophenyl)perfluorocyclobutane, 1,2-bis(3- or 4-aminophenyl)perfluorocyclobutene, -cyclopentene and -cyclohexene, by reaction with aromatic carboxylic anhydrides. The polyimides are useful for coatings and films.
    Type: Grant
    Filed: October 14, 1993
    Date of Patent: August 15, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Zhenyu Yang
  • Patent number: 5436310
    Abstract: Novel aromatic poly(ether ketones) having imide, amide, ester, azo, quinoxaline, benzimidazole, benzoxazole, or benzothiazole groups, comprising, for example, a repeat unit ##STR1## are prepared by Friedel Crafts polymerization.
    Type: Grant
    Filed: June 29, 1989
    Date of Patent: July 25, 1995
    Assignee: Raychem Corporation
    Inventors: Klaus J. Dahl, Patrick J. Horner, Heinrich C. Gors, Viktors Jansons, Richard H. Whiteley
  • Patent number: 5434240
    Abstract: Disclosed herein are novel poly(imide-ethers) containing ortho substitution in the main chain of the polymer. These polymers are made from novel aromatic bis-carboxylic anhydrides which contain two ether groups attached to an aromatic ring in ortho positions to each other. The polymers are particularly useful for films, fibers and encapsulation, as well as thermoplastics.
    Type: Grant
    Filed: April 29, 1994
    Date of Patent: July 18, 1995
    Assignee: The University of Liverpool
    Inventors: Geoffrey C. Eastmond, Jerzy Paprotny
  • Patent number: 5432256
    Abstract: The present invention provides a liquid crystal aligning film having a reduced after image and a good liquid crystal aligning property caused by a rubbing treatment of a thin film consisting of organics, and its liquid crystal display device.
    Type: Grant
    Filed: June 7, 1993
    Date of Patent: July 11, 1995
    Assignee: Chisso Corporation
    Inventors: Yukino Abe, Minoru Nakayama, Shizuo Murata
  • Patent number: 5428102
    Abstract: A series of polyimides based on the dianhydride of 1,4-bis(3,4-dicarboxyphenoxy)benzene (HQDEA) or on 2,2-bis[4(3-aminophenoxy)phenyl]hexafluoropropane (3-BDAF) are evolved from high molecular weight polyamic acid solutions yielding flexible free-standing films and coatings in the fully imidized form which have a dielectric constant in the range of 2.5 to 3.1 at 10 GHz.
    Type: Grant
    Filed: May 2, 1994
    Date of Patent: June 27, 1995
    Assignee: The United States of America as represented by the United States National Aeronautics and Space Administration
    Inventors: Anne K. St. Clair, Terry L. St. Clair, William P. Winfree
  • Patent number: 5420234
    Abstract: Bis-N-aminoimides of formula (III): ##STR1## wherein m is 0 or 1 and ##STR2## is a mono- or polycyclic aromatic radical, can be employed to produce a variety of polymers of the type produced from diamines, including polyimides having an N--N linkage; polymers can be produced having exceptionally high glass transition temperatures, but which are also soluble in organic solvents; colored polymers and electroconductive polymers and photoconductive polymers can also be produced.
    Type: Grant
    Filed: July 26, 1994
    Date of Patent: May 30, 1995
    Inventors: Allan S. Hay, Hossein Ghassemi
  • Patent number: 5420233
    Abstract: An agent for vertical orientation treatment consisting essentially of a polyimide which contains a linear alkyl group having at least 12 carbon atoms in an amount of at least 5% by weight of the alkyl group to the total weight of the polyimide, and which, when a coating film of the polyimide is formed on a substrate, has a surface energy of not more than 38 dyn/cm.
    Type: Grant
    Filed: June 15, 1993
    Date of Patent: May 30, 1995
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Hideyuki Isogai, Toyohiko Abe
  • Patent number: 5420232
    Abstract: The present invention relates to an improved process for making polyamic ester comprising reacting an aromatic diester diacid halide with the monohydrohalide salt of an aromatic diamine in the presence of a base. The polyamic ester can be imidized to form a polyimide suitable for use in electronic components.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: May 30, 1995
    Assignee: International Business Machines Corporation
    Inventors: Daniel J. Dawson, Richard A. DiPietro
  • Patent number: 5414070
    Abstract: Disclosed is a poly(amide-ether-imide) and the preparation of the same. An ether chain-containing aromatic diamine is subject to thermal condensation with trimellitic anhydride (TMA) in a polar solvent to obtain diimide dicarboxylic acid, followed by polycondensing the diimide dicarboxlic acid with diamine to form the poly(amide-ether-imide). The poly(amide-ether-imide) of the present invention has superior strength, heat resistance, and processability. The preparation of the present invention is simple and economic.
    Type: Grant
    Filed: December 3, 1993
    Date of Patent: May 9, 1995
    Assignee: National Science Council
    Inventors: Chin-Ping Yang, Sheng-Huei Hsiao, Jiun-Hung Lin
  • Patent number: 5412065
    Abstract: Polyimide oligomers are described which comprise the intercondensation product of a monomer mixture comprising (A) at least one aromatic bis(ether anhydride), (B) at least one phenylindane diamine, and (C) at least one end-cap monomer selected from the group consisting of monoanhydrides, acyl halides and amines, wherein each end-cap monomer (C) contains at least one crosslinkable group in the molecule and wherein the phenylindane diamine component (B) is present in the mixture in a stoichiometric excess. The monomers react in a suitable solvent under an inert atmosphere to form polyimide oligomers having a number average molecular weight of from about 1,000 to about 15,000. The polyimide oligomers of the present invention are readily processed to form polyimide matrix resins with high temperature and oxidative stability.
    Type: Grant
    Filed: April 9, 1993
    Date of Patent: May 2, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Michael Amone, Mark Southcott
  • Patent number: 5412066
    Abstract: Four phenylethynyl amine compounds--3 and 4-aminophenoxy-4'-phenylethynylbenzophenone, and 3 and 4-amino-4'-phenylethynylbenzophenone--were readily prepared and were used to endcap imide oligomers. Phenylethynyl-terminated amide acid oligomers and phenylethynyl-terminated imide oligomers with various molecular weights and compositions were prepared and characterized. These oligomers were cured at 300.degree. C. to 400.degree. C. to provide crosslinked polyimides with excellent solvent resistance, high strength and modulus and good high temperature properties. Adhesive panels, composites, films and moldings from these phenylethynyl terminated imide oligomers gave excellent mechanical performance.
    Type: Grant
    Filed: March 3, 1994
    Date of Patent: May 2, 1995
    Assignee: Ther United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Paul M. Hergenrother, Robert G. Bryant, Brian J. Jensen, Stephen J. Havens
  • Patent number: 5407657
    Abstract: Novel MRI contrast agents that comprise one or more metal-ion chelates in juxtaposition with one or more free-radical nitroxide compounds in a polymeric or oligomeric molecule. Both the chelate units and the free radical units may, independently, be inside the main chain of the polymer or in a side chain of the linkage portion of the polymer. The number of combined units of chelates and free radicals in the polymer or oligomer is at least two.
    Type: Grant
    Filed: February 28, 1994
    Date of Patent: April 18, 1995
    Inventors: Evan C. Unger, GuanLi Wu
  • Patent number: 5399664
    Abstract: The invention relates generally to polymers exhibiting second order nonlinear optical properties, and characterized by high thermal stability. Disclosed are polymers prepared by a polycondensation reaction between an aromatic dianhydride and a compound selected from the group consisting of a di(alkylamino)amine and an aromatic diamine. Most preferred are polymers that are the products of a polycondensation reaction between 1,2,4,5-benzenetetracarboxylic dianhydride and nitro(N,N-diethylamino)stilbene, wherein the polymer is imidized by further heat treatment.
    Type: Grant
    Filed: November 10, 1993
    Date of Patent: March 21, 1995
    Assignee: Arch Development Corporation
    Inventors: Zhonghua Peng, Luping Yu
  • Patent number: 5399655
    Abstract: This invention concerns positive-working photodefinable polyimide precursors which make use of chemical amplification based on photoacid catalyzed cleavage of acid labile-poly(amic acetal esters).
    Type: Grant
    Filed: October 29, 1993
    Date of Patent: March 21, 1995
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Howard E. Simmons, III
  • Patent number: 5395917
    Abstract: Thermoplastic poly(imide-esters) and poly(imide-amides) with repeat units derived from the title amino acid. In the polymer the amino group becomes part of an imide group and the carboxyl group becomes part of an ester or amide group. The polymers have a good balance of properties, making them useful for melt forming shaped articles, films and fibers.
    Type: Grant
    Filed: May 21, 1993
    Date of Patent: March 7, 1995
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Robert S. Irwin
  • Patent number: 5395918
    Abstract: The invention describes new biphenyl dianhydrides, and new polyimides and copolyimides made from the dianhydrides. The synthesized polyimides exhibit significantly enhanced solubility when the biphenyl dianhydrides are substituted, particularly at the 2 and 2' positions on the phenyl rings.
    Type: Grant
    Filed: April 21, 1994
    Date of Patent: March 7, 1995
    Assignee: The University of Akron
    Inventors: Frank W. Harris, Sheng-Hsien Lin
  • Patent number: 5393864
    Abstract: A random polyimide copolymer, based on a rigid dianhydride, a rigid diamine and an additional diamine and/or dianhydride containing one or more flexibilizing linkages. Soft-baked coatings of the poly(amic acid) precursor are readily processed using conventional aqueous base developers, such as tetramethylammonium hydroxide. The polyimide and soft-baked coatings are useful as a dielectric layer In multichip module applications or as a stress buffer coating.
    Type: Grant
    Filed: April 26, 1993
    Date of Patent: February 28, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: John D. Summers
  • Patent number: 5391697
    Abstract: Thermosetting esterimide oligomers of formulas (IA) and (IB) are disclosed: ##STR1## where A.sub.1, A.sub.2 and A.sub.4 are divalent organic groups, A.sub.3 is a monovalent organic group and A.sub.1, A.sub.2, A.sub.3 and A.sub.4 may be the same or different, with m being an integer of 1-30. The above compounds provide hard substances having excellent workability, heat resistance and mechanical properties.
    Type: Grant
    Filed: March 8, 1994
    Date of Patent: February 21, 1995
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventor: Hiroyuki Furutani
  • Patent number: 5385719
    Abstract: Novel compounds having use as contrast agents in magnetic resonance imaging, as well as other uses, are described. The compounds are comprised of a copolymer which comprises at least two of a first monomer of the formula X.sub.1 --(CHR.sub.2 CHR.sub.2 --Y).sub.n --(CHR.sub.2).sub.m --CHR.sub.2 CHR.sub.2 --X.sub.2, wherein X.sub.1 and X.sub.2 are, independently, OH, NH.sub.2, NHR.sub.1, COOH, COOR.sub.1, SH, or Z, Y is O, NH, NR.sub.1, S, or CO, n is 0-10,000, m is 0 or 1, each Z is, independently, Cl, Br, or I, each R.sub.1 is, independently, a C.sub.1 -C.sub.20 substituted alkyl or cycloalkyl, and each R.sub.2 is, independently, H or OH, and at least one of a second monomer which is a polynitrilo chelating agent having at least two COOH, COOR.sub.1, or COZ groups, the first and second monomers being bound to one another to form a copolymer through an ester, amide, or carboxylic thioester linkage of at least one of the OH, NH.sub.2, NHR.sub.1, COOH, COOR.sub.
    Type: Grant
    Filed: September 22, 1992
    Date of Patent: January 31, 1995
    Inventors: Evan C. Unger, Guanli Wu
  • Patent number: 5384390
    Abstract: There are disclosed flame-retardant, high temperature resistant polyimide fibers of the general formula ##STR1## wherein n is an integer larger than 1, A is a tetravalent aromatic group and R is at least one divalent aromatic group. These polyimide fibers have been heat-treated in the unstretched state and have a maximum shrinkage of 14% when heated to a temperature of 400.degree. C. These polyimide fibers are produced by initially spinning crude fibers from a solution of the appropriate polyimide in an aprotic organic solvent, preferably according to the dry-spinning method, which solution optionally contains additives. The crude fibers obtained are washed with water to remove the solvent. The washed crude fibers are dried to a moisture content of less than 5% by mass, are subjected to a heat treatment at a temperature of between 315.degree. C and 450.degree. C, are cooled and, if desired, are crimped and cut to staple fibers.
    Type: Grant
    Filed: September 23, 1991
    Date of Patent: January 24, 1995
    Assignee: Lenzing Aktiengesellschaft
    Inventors: Claus Schobesberger, Klaus Weinrotter, Herbert Griesser, Sigrid Seidl
  • Patent number: 5380820
    Abstract: In one aspect, the present invention relates to polyimides having excellent thermal resistance and process for preparing the same comprising carrying out condensation of 4,4'-bis(3-aminophenoxy)biphenyl with pyromellitic dianhydride in the presence of a different diamine compound and optionally with a different tetracarboxylic acid dianhydride.In a second aspect, the present invention relates to a heat resistant resin composition consisting essentially of an aromatic polyetherimide and a defined polyimide.In a third aspect, the present invention relates to a polyimide resin composition comprised on a defined polyimide and a separate high-temperature engineering polymer.In a fourth aspect, the present invention relates to a resin composition comprised of a defined polyimide and an aromatic polyamideimide.
    Type: Grant
    Filed: December 7, 1993
    Date of Patent: January 10, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Masahiro Ohta, Masao Yoshikawa
  • Patent number: 5374708
    Abstract: Polyimide filaments and polyimide films having great strength, high elastic modulus and high crystallinity and comprising a novel polyimide which can be melt-processed without impairing high crystallinity and which essentially consists of recurring structural units represented by the formula (I): ##STR1## more than 85 mol % the polyimide consists of recurring structural units of the formula (II): ##STR2## and from 0.5 to 15 mol % of the polyimide consists of recurring structural units represented by the formula (III), the formula (II) exclusive, the formula (IV) and/or the formula (V).
    Type: Grant
    Filed: August 8, 1991
    Date of Patent: December 20, 1994
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Shoji Tamai, Masahiro Ohta, Akihiro Yamaguchi, Masumi Saruwatari
  • Patent number: 5371172
    Abstract: An unsaturated alkyd having a number-average molecular weight of at least 5000 and having terminal carboxyl groups is provided by esterification and then deglycolization reaction of an .alpha.,.beta.-unsaturated polybasic acid or an polyhydroxy alcohol followed by reaction with polybasic acid anhydride to substitute more than 10 mole % of terminal hydroxyl groups with carboxyl groups. High molecular weight unsaturated polyester resin is also provided by formulating the unsaturated alkyd with a copolymerizable monomer such as styrene. The polyester resin can be widely used in a various applications by employing the excellent physical properties thereof.
    Type: Grant
    Filed: March 24, 1992
    Date of Patent: December 6, 1994
    Assignee: Showa Highpolymer Co., Ltd.
    Inventors: Eiichiro Takiyama, Isamu Niikura, Takao Hokari
  • Patent number: 5371168
    Abstract: Amorphous polyimide powder which has recurring structural units of the formula (I): ##STR1## as a fundamental skeleton, is blocked at the polymer chain end with dicarboxylic anhydride represented by the formula (II) ##STR2## wherein Z is a divalent radical having from 6 to 27 carbon atoms and selected from the group consisting of a monoaromatic radical, condensed polyaromatic radical and noncondensed aromatic radical connected to each other with a direct bond or a bridge member, and essentially has no reactive radical at the polymer chain end, preparation process of the amorphous polyimide powder, heat-resistant adhesive comprising the polyimide, and bonding method using the adhesive.
    Type: Grant
    Filed: June 5, 1992
    Date of Patent: December 6, 1994
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Wataru Yamashita, Shoji Tamai, Akihiro Yamaguchi
  • Patent number: RE34820
    Abstract: Sizing for 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 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.2 --;T=methallyl or allyl;Me=methyl; andR=hydrogen, lower alkyl, or phenyl.Prepregs and composites having carbon fibers sized with such polyamideimides are also described.
    Type: Grant
    Filed: November 15, 1993
    Date of Patent: January 3, 1995
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard, Ronald R. Stephenson