Reactant Contains Three Or More Carboxylic Acid Groups Or Is Derivative Thereof Patents (Class 528/188)
  • 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: 5470943
    Abstract: This invention relates to a novel fluorine-containing polyimide or polyimide copolymer being colorless and having transparency and very low dielectric characteristics, and has a novel aromatic diamino compound used for the polyimide, a preparation process thereof, a polyimide-based resin composition comprising the polyimide or polyimide copolymer and a fibrous reinforcement, a process for preparing the resin composition, an injection molded article of the resin composition.
    Type: Grant
    Filed: December 21, 1994
    Date of Patent: November 28, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Yoshihiro Sakata, Wataru Yamashita, Yuichi Okawa, Shoji Tamai, Tsutomu Ishida, Mitsunori Matsuo, Keizaburo Yamaguchi, Akihiro Yamaguchi
  • 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: 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: 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: 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: 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: 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: 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: 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: 5442031
    Abstract: Soluble polyimides are formed from oxydiphthalic anhydride and 2,4-diaminotoluene. Optionally, up to 30 mole % of an alternate diamine and up to 50 mole % of an alternate dianhydride can be used with the oxydiphthalic anhydride and 2,4-diaminotoluene.
    Type: Grant
    Filed: April 21, 1994
    Date of Patent: August 15, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Beth E. Dunlap
  • 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: 5432248
    Abstract: A thermotropic polyesterimide, in which the liquid-crystalline phase is of nematic structure within a useful temperature range, consists of units of formula: ##STR1## the units being in the following ratios:a/(b+c)=1c/b=0-50/50, and preferably c/b<30/70The polyesterimide of the present invention possesses self-reinforcement characteristics, or reinforcement characteristics for traditional thermoplastic materials.
    Type: Grant
    Filed: April 7, 1993
    Date of Patent: July 11, 1995
    Assignee: Eniricerche S.p.A.
    Inventors: Cesarina Bonfanti, Alessandro Lezzi, Ugo Pedretti, Arnaldo Roggero, Francesco P. La Mantia
  • 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: 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: 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: 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: 5410012
    Abstract: Novel poly(N-arylenebenzimidazole)s (PNABIs) are prepared by the aromatic nucleophilic displacement reaction of novel di(hydroxyphenyl-N-arylene benzimidazole) monomers with activated aromatic dihalides or activated aromatic dinitro compounds. The polymerizations are carried out in polar aprotic solvents such as N-methyl-2-pyrrolidinone or N,N-dimethylacetamide using alkali metal bases such as potassium carbonate at elevated temperatures under nitrogen. The di(hydroxyphenyl-N-arylenebenzimidazole) monomers are synthesized by reacting phenyl-4-hydroxybenzoate with bis(2-aminoanilino)arylenes in diphenylsulfone. Moderate molecular weight PNABIs of new chemical structures were prepared that exhibit a favorable combination of physical and mechanical properties. The use of the novel di(hydroxyphenyl-N-arylenebenzimidazole)s permits a more economical and easier way to prepare PNABIs than previous routes.
    Type: Grant
    Filed: March 5, 1993
    Date of Patent: April 25, 1995
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: John W. Connell, Paul M. Hergenrother, Joseph G. Smith, Jr.
  • Patent number: 5405936
    Abstract: Liquid-melt aliphatic dicarboxylic acids tend to undergo undesirable discoloration during prolonged storage. The discoloration can be avoided by an addition of 0.1 to 3.0% by weight of a primary amine.
    Type: Grant
    Filed: March 4, 1994
    Date of Patent: April 11, 1995
    Assignee: Huels Aktiengesellschaft
    Inventors: Salih Mumcu, Franz-Erich Baumann
  • 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: 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: 5378420
    Abstract: A process for preparing polyimide fibers involves the preparation of a polymer in p-chlorophenol from reactants comprising 2,2'-dimethyl-4,4'-diaminobiphenyl and a tetracarboxylic anhydride. Following its preparation, the polyimide fibers can be spun directly from the reaction mixture. In a preferred embodiment, the dianhydride comprises 3,3',4,4'-biphenyltetracarboxylic dianhydride.
    Type: Grant
    Filed: June 16, 1993
    Date of Patent: January 3, 1995
    Assignee: Edison Polymer Innovation Corporation
    Inventors: Frank W. Harris, Stephen Z. D. Cheng
  • 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: 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: 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: 5357033
    Abstract: Film forming aromatic organic polymers are provided having a dielectric constant greater than 3 resulting from the polymerization of aromatic organic monomers having orientable organic dipolar groups with a net dipole moment of at least 0.5 Debye. Among the aromatic organic polymers are included polyimides and polyetherimides having repeat main chain groups with orientable organic dipolar groups with non-symmetrically positioned polar radicals, such as fluoro and nitrile.
    Type: Grant
    Filed: April 1, 1993
    Date of Patent: October 18, 1994
    Assignee: General Electric Company
    Inventors: John T. Bendler, Tohru Takekoshi, Clive W. Reed
  • Patent number: 5354839
    Abstract: A polyimide comprising a requisite structural unit having one or more recurring structural units of the formula: ##STR1## such as the structural units of the formula ##STR2## The polyimide can have an extremely low dielectric constant and is colorless, transparent and excellent in processability and heat resistance, and also provides an aromatic diamine which is useful as a raw material monomer of the polyimide or a raw material of other various engineering plastics.
    Type: Grant
    Filed: March 31, 1993
    Date of Patent: October 11, 1994
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Wataru Yamashita, Yoshihiro Sakata, Toshiyuki Kataoka, Yuichi Okawa, Hideaki Oikawa, Tadashi Asanuma, Mitsunori Matsuo, Tsutomu Ishida, Keizaburo Yamaguchi, Akihiro Yamaguchi
  • Patent number: 5346982
    Abstract: A polyimide-based heat-resistant adhesive having excellent peel strength and heat resistance comprising polyimide composed of 10 to 99% by mole of structural units having the formula (1) and 1 to 90% by mole of structural units having the formula (2) or comprising polyamic acid precursor which corresponds to the polyimide.
    Type: Grant
    Filed: June 7, 1993
    Date of Patent: September 13, 1994
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Shoji Tamai, Katsuaki Iiyama, Akihiro Yamaguchi
  • Patent number: 5344916
    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: June 4, 1993
    Date of Patent: September 6, 1994
    Assignee: The University of Akron
    Inventors: Frank W. Harris, Stephen Z. D. Cheng
  • Patent number: 5340914
    Abstract: A method and apparatus are disclosed for conducting a physical process and a chemical reaction by exposing a material containing a volatile substance to microwave radiation where the morphology of said material will change when exposed to such radiation. The power of said radiation is adjusted over time as the morphology of the material changes to maximize the effect of the radiation in order to produce a product in a minimum amount of time that is substantially free of said volatile substance.The method and apparatus can also be used to conduct such a process or reaction with materials that do not contain a volatile material.In one embodiment a method and apparatus are disclosed for manufacturing a polyimide from a precursor in a solvent by exposing the precursor to microwave radiation in a tuneable microwave resonant cavity that is tuned during imidization to achieve critical coupling of the system. Microwave power is controlled to remove the solvent and obtain the desired level of reaction.
    Type: Grant
    Filed: June 16, 1993
    Date of Patent: August 23, 1994
    Assignee: International Business Machines Corporation
    Inventors: Jerome J. Cuomo, Jeffrey D. Gelorme, Michael Hatzakis, Jr., David A. Lewis, Jane M. Shaw, Stanley J. Whitehair
  • Patent number: 5340904
    Abstract: A compound or polymer having a bis(phenoxy)naphthalene structure, a high molecular weight, and very good mechanical performance and heat-resistivity is provided. The polymer can be polyamides, polyimides or poly(amide-imide)s and can have a basic structure of ##STR1## wherein R1 is a naphthalene ring.
    Type: Grant
    Filed: December 29, 1992
    Date of Patent: August 23, 1994
    Assignee: National Science Council
    Inventors: Chin-Ping Yang, Wen-Tung Chen
  • Patent number: 5338826
    Abstract: A structure which is effective as an electrical insulator or as a transmitter-receiver of electromagnetic energy is prepared by providing a suitable substrate and covering the substrate with an adhering layer of a low dielectric, high temperature, linear aromatic polyimide.
    Type: Grant
    Filed: September 28, 1992
    Date of Patent: August 16, 1994
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administation
    Inventors: Anne K. St. Clair, Terry L. St. Clair, William P. Winfree
  • Patent number: 5334697
    Abstract: A polyimide gas separation membrane containing repeating units derived from 9,9-disubstituted xanthene dianhydride is disclosed.
    Type: Grant
    Filed: October 4, 1993
    Date of Patent: August 2, 1994
    Assignee: L'Air Liquide, S.A.
    Inventor: John W. Simmons
  • Patent number: 5332799
    Abstract: In solutions of polyimide-forming starting materials, containing diamines and tetracarboxylic diesters, at least 2 mol % of the ester groups in the tetracarboxylic diesters are derived from alcohols of the general formulaHO--Z--O--X IorHO--Z--X IIwhere Z is a straight-chain or branched aliphatic radical of from 1 to 15 carbon atoms which can be interrupted by from 1 to 4 ether groups --O-- and X is an aromatic radical of from 5 to 20 carbon atoms which can also contain nitrogen, oxygen or sulfur as hetero atoms in the aromatic ring system, excepting benzyl alcohol as compound of the formula II in the case of the use of diamines having a basicity constant of less than or equal to 10.sup.-11.
    Type: Grant
    Filed: November 2, 1992
    Date of Patent: July 26, 1994
    Assignee: BASF Lacke+Farben Aktiengesellschaft
    Inventors: Rainer Blum, Hans J. Heller, Klaus Lienert
  • Patent number: 5328979
    Abstract: Copolyimide compositions and methods for their preparation which are melt-processible at relative low pressures, i.e. less than 1000 psi, and are suited for laminating and molding, are described. The invention additionally encompasses copolyimide precursors, reinforced polyimide composites and laminates made from said polyimides where the composite is reinforced by fibrous materials. This is achieved by reacting at least one aromatic dianhydride where each anhydride group is located on an aromatic ring with the carbonyl units in an ortho orientation relative to one another, with at least one diamine which is capable of a transmidization reaction upon incorporation into the polyimide backbone, and with at least one other diamine which is not capable of undergoing such reaction, the diamine which is capable of undergoing the transimidization reaction being present in an amount of from about 1-50 mole percent in relation to the diamine that is not susceptable to transimidization.
    Type: Grant
    Filed: November 16, 1992
    Date of Patent: July 12, 1994
    Assignee: The University of Akron
    Inventors: Frank Harris, Patricia A. Gabori
  • Patent number: 5324810
    Abstract: Polyimide compositions, films, and electronic devices using polyimides, based on 9-aryl-9(perfluoroalkyl)xanthene-2,3,6,7-dianhydride or 9,9'-bis(perfluoroalkyl)xanthene-2,3,6,7-dianhydride and benzidine derivatives. These polyimides offer a combination of low linear coefficient of thermal expansion, low dielectric constant, and low water absorption.
    Type: Grant
    Filed: October 23, 1992
    Date of Patent: June 28, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Brian Auman
  • Patent number: 5324813
    Abstract: Low dielectric constant polyimides formed from an optionally fluorinated dianhydride and a fluorinated diamine are described. The fluorine containing constituents are sterically disposed so that the dipole moment of the constituents tend to cancel out. Since fluorine containing diamines are generally nonreactive, to achieve a polyimide of high enough molecular weight to be practically useful, a method of fabrication of a high molecular weight polymer from monomers of low reactivity is provided. The monomers, such as a diamine and dianhydride are provided in a solution within which a low molecular weight polyamic acid is formed. The solution is dried. The polyamic acid used is cured to a low molecular weight polyimide. The polyimide is redisolved, redryed and recured enough times to build up the molecular weight to a useful level. The method is applicable to fabricating other polymers of high molecular weight, such as polyamides, polyesters and polyurethanes.
    Type: Grant
    Filed: July 22, 1992
    Date of Patent: June 28, 1994
    Assignee: International Business Machines Corporation
    Inventors: Gareth G. Hougham, Jane M. Shaw, Alfred Viehbeck
  • Patent number: 5322924
    Abstract: Addition polyimide resins having improved thermo-oxidative stability and enhanced processability are prepared by the reaction of a mixture of monomers comprising a non-planar polyphenyl diamine (a), a diester of tetracarboxylic acid or the corresponding dianhydride (b) and an end-capping agent (c), or a diamine (d), a non-planar polyphenyl diester or dianhydride of a tetracarboxylic acid (e) and an end-capping agent (c).
    Type: Grant
    Filed: October 7, 1991
    Date of Patent: June 21, 1994
    Assignee: The United States of America as represented by the United States National Aeronautics and Space Administration
    Inventors: Chun-Hua K. Chuang, Raymond D. Vannucci
  • Patent number: 5321096
    Abstract: A thermoplastic resin composition comprise 99.9.about.50 parts by weight of one or more thermoplastic resin selected from the group consisting of aromatic polyimide, aromatic polyetherimide, aromatic polyamideimide, aromatic polyethersulfone and aromatic polyether ketone and 0.1.about.50 parts by weight of one or more liquid crystal type aromatic polyimide having recurring structural units represented by the formula (1): ##STR1## wherein R.sub.1 .about.R.sub.5 is a hydrogen atom, fluorine atom, trifluoromethyl, methyl, ethyl or cyano and may be the same or different, and R is a tetravalent radical having 6.about.27 carbon atoms and being selected from the group consisting of a monoaromatic radical, condensed polyaromatic radical and noncondensed aromatic radical connected each other with a direct bond or a bridge member.
    Type: Grant
    Filed: March 22, 1993
    Date of Patent: June 14, 1994
    Assignee: Mitsui Toatsu Chemical, Incorporated
    Inventors: Yuichi Okawa, Nobuhito Koga, Hideaki Oikawa, Tadashi Asanuma, Akihiro Yamaguchi
  • Patent number: 5320886
    Abstract: This invention relates primarily to organofunctional monomers, predominantly dimethacrylates and/or diacrylates containing one or more (predominantly two carboxyl groups, with moieties that provide sufficient affinity with water to allow any desired amount of water and/or miscible fugitive solvents to be mixed homogeneously with these monomers and formulations containing them. The activity of water in the monomer formulations can be adjusted so that it is equal to the water activity in biological tissues. This promotes biocompatibility and enhances the adhesive characteristics of polymers prepared from these formulations. Probability statistics are disclosed that optimize the compositions of polymer reaction products.
    Type: Grant
    Filed: November 14, 1991
    Date of Patent: June 14, 1994
    Assignee: American Dental Association Health Foundation
    Inventor: Rafael L. Bowen
  • Patent number: 5317082
    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: December 22, 1992
    Date of Patent: May 31, 1994
    Assignee: Amoco Corporation
    Inventors: Allyson J. Beuhler, David A. Wargowski
  • 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