Reactant Contains Three Or More Carboxylic Acid Groups Or Is Derivative Thereof Patents (Class 528/188)
  • Patent number: 5955568
    Abstract: The disclosure describes a process for preparing a polyamideimide resin having high molecular weight in a simple manner wherein major problems of the prior processes such as low heat resistance and low melt flowability are improved. The process comprises condensation of an aromatic tricarboxylic acid anhydride and an aromatic diamine in a polar solvent, subjecting the resulting diimidedicarboxylic acid to acyl halogenating agent treatment to give an intermediate having good reactivity at low temperature, and then subjecting the latter to direct polymerization by using diamine as a nucleophilic agent to give a polyamideimide resin having high molecular weight. The polyamideimide resin prepared by the present invention can be used as major heat resistant structural material in advanced industries and as paint, sheet, adhesives, sliding material, fiber and film having heat resistance.
    Type: Grant
    Filed: October 23, 1997
    Date of Patent: September 21, 1999
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Kil-Yeong Choi, Dong-Hack Suh, Mi-Hie Yi, Young-Taik Hong, Moon-Young Jin
  • Patent number: 5952453
    Abstract: Methylenedianiline-free, PMR-type, curable compositions based on m-phenylenediamine or mixtures of m-phenylenediamine and p-phenylenediamine are described.
    Type: Grant
    Filed: May 8, 1996
    Date of Patent: September 14, 1999
    Assignee: Cytec Technology Corp.
    Inventors: Patrick T. McGrail, Paul Eustace, William S. Dewar
  • Patent number: 5939521
    Abstract: This invention relates the novel diamines, the polyimide oligomers and the polyimides derived therefrom and to the method of preparing the diamines, oligomers and the polyimides. The thermoplastic polyimides derived from the aromatic diamines of this invention are characterized as having a high glass transition temperature, good mechanical properties and improved processability in the manufacture of adhesives, electronic and composite materials for use in the automotive and aerospace industry. The distinction of the novel aromatic diamines of this invention is the 2,2',6,6'-substituted biphenyl radicals which exhibit noncoplanar conformation that enhances the solubility of the diamine as well as the processability of the polyimides, while retaining a realatively high glass transition temperature and improved mechanical properties at useful temperature ranges.
    Type: Grant
    Filed: January 23, 1998
    Date of Patent: August 17, 1999
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Chun-Hua K. Chuang
  • Patent number: 5932688
    Abstract: An improved polybenzimidazole wherein the total concentration of metals other than alkali metal and alkaline earth metals is 10 ppm or less. The resulting polybenzimidazole is industrially useable in parts or components of apparatus for the manufacture of semiconductors and display devices.
    Type: Grant
    Filed: January 14, 1997
    Date of Patent: August 3, 1999
    Assignee: Hoechst Japan Limited
    Inventor: Makoto Murata
  • Patent number: 5929201
    Abstract: The present invention relates to amine compositions and the preparation of polyimides. The polyimides can be used for inducing alignment of a liquid crystal medium with polarized light and liquid crystal display elements.
    Type: Grant
    Filed: May 20, 1997
    Date of Patent: July 27, 1999
    Assignee: Elsicon, Inc.
    Inventors: Wayne M. Gibbons, Paul J. Shannon, Shao-Tang Sun
  • Patent number: 5925475
    Abstract: Phthalonitrile thermoset polymers and composites having flame resistance formed by combining a phthalonitrile monomer in the melt stage with a halogen-containing aromatic amine curing agent. The halogen-containing aromatic amine curing agent is selected from the group consisting of aromatic amine curing agents having the general formula:NH.sub.2 --(Ar.sup.2 O--).sub.y Ar.sup.1 --X--Ar.sup.1 (--OAr.sup.2).sub.y --NH.sub.2wherein Ar.sup.1 and Ar.sup.2 are substituted or unsubstituted aromatic groups, y is 0 or greater, and X is --C(CF.sub.3).sub.2 -- and aromatic amine curing agents having the general formula:NH.sub.2 --(Ar.sup.4 O--).sub.u Ar.sup.3 --Z--Ar.sup.3 (--OAr.sup.4).sub.u --NH.sub.2wherein Z is a connecting bond or a linking group other than oxygen or --C(CF.sub.3).sub.2 --, u is 0 or greater, and Ar.sup.3 and Ar.sup.4 are aromatic groups and wherein either Ar.sup.3 or Ar.sup.1 or both Ar.sup.3 and Ar.sup.4 are substituted with at least one halogen atom or halo-substituted alkyl group.
    Type: Grant
    Filed: October 2, 1997
    Date of Patent: July 20, 1999
    Assignee: United States of America as represented by the Secretary of the Navy
    Inventors: Satya B. Sastri, Teddy M. Keller
  • Patent number: 5914385
    Abstract: An addition type polyimide resin raw material composition having high heat resistance and high corrosion resistance comprising a tetracarboxylic anhydride and/or tetracarboxylic diester compound, diamine compound and exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride and/or exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic monoester compound; a composition containing a prepreg; a fiber-reinforced polyimide composite prepreg, coating material and paint using them; and a curing method thereof.
    Type: Grant
    Filed: December 4, 1996
    Date of Patent: June 22, 1999
    Assignee: Mitsubishi Jukogyo Kabushiki Kaisha
    Inventors: Noriya Hayashi, Naomoto Ishikawa, Yukihiro Sakaguchi, Shunichi Hayashi, Hitoshi Noda
  • Patent number: 5914354
    Abstract: A photosensitive resin composition comprising;(A) a polyimide precursor containing an acrylic or methacrylic group;(B) a tertiary amine compound represented by the general formula: ##STR1## wherein R.sup.6 is a monovalent organic group having 3 or less carbon atoms, R.sup.7 is a divalent organic group having 3 or less carbon atoms, and R.sup.8 is a hydrogen atom or a methyl group; and(C) at least one of a photopolymerization initiator and a sensitizer.This composition has a sufficient sensitivity even when thick films are formed, has a superior developability in an aqueous alkali solution, and is suited for the formation of polyimide patterns.
    Type: Grant
    Filed: August 12, 1997
    Date of Patent: June 22, 1999
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventor: Hideto Kato
  • Patent number: 5908915
    Abstract: Copolyetherimides are prepared by the reaction of an alkali metal salt of a dihydroxyaromatic compound with a bis(substituted phthalimide) and a third compound which may be a substituted aromatic ketone or sulfone or a macrocyclic polycarbonate or polyarylate oligomer. The reaction takes place the in presence of a solvent and a phase transfer catalyst having high thermal stability, such as a hexaalkylguanidinium halide. Random or block copolymers may be obtained, depending on the reaction conditions.
    Type: Grant
    Filed: October 6, 1997
    Date of Patent: June 1, 1999
    Assignee: General Electric Company
    Inventor: Daniel Joseph Brunelle
  • Patent number: 5902876
    Abstract: Improved process for producing a polybenzimidazole compound in solution by dissolving a fully dried polybenzimidazole of the following general formula (1) or (2) in N,N-dimethylacetamide of a sufficiently reduced water content at an elevated temperature of 260.degree. C. or higher in an inert gas atmosphere and a solution of the polybenzimidazole compound produced by the process. The solution remains useful for an extended time without using metal salts or any other stabilizers: ##STR1## where R.sup.1, R.sup.2 and R.sup.5 are tetra-, di- and trivalent aromatic groups, respectively; R.sup.3, R.sup.4 and R.sup.6 are each independently a hydrogen atom, an alkyl group or an aryl group; n is an integer of 2 or more.
    Type: Grant
    Filed: June 18, 1997
    Date of Patent: May 11, 1999
    Assignee: Hoechst Japan Limited
    Inventors: Makoto Murata, Toru Nakamura
  • Patent number: 5889139
    Abstract: Novel polyimide copolymers containing ether linkages were prepared by the reaction of an equimolar amount of dianhydride and a combination of diamines. The polyimide copolymers described herein possess the unique features of low moisture uptake, dimensional stability, good mechanical properties, and moderate glass transition temperatures. These materials have potential application as encapsulants and interlayer dielectrics.
    Type: Grant
    Filed: February 28, 1997
    Date of Patent: March 30, 1999
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Catharine C. Fay, Anne K. St. Clair
  • Patent number: 5886131
    Abstract: A method for synthesizing 1,4-bis(4-aminophenoxy)naphthalene and a series of polyamides, polyimides and copoly(amide-imide)s derived from the said compound is disclosed. These polymers possess excellent thermal stability and mechanical strength.
    Type: Grant
    Filed: May 30, 1997
    Date of Patent: March 23, 1999
    Assignee: China Textile Institute
    Inventors: Shin Chuan Yao, Jongfu Wu, Kun-Lin Cheng, Wen-Tung Chen
  • Patent number: 5866676
    Abstract: Polyimide copolymers were prepared by reacting different ratios of 3,4'-oxydianiline (ODA) and 1,3-bis(3-aminophenoxy)benzene (APB) with 3,3',4,4'-biphenylcarboxylic dianhydride (BPDA) and endcapping with an effective amount of a non-reactive endcapper. Within a narrow ratio of diamines, from .sup..about. 50% ODA/50% APB to .sup..about. 95% ODA/5% APB, the copolyimides prepared with BPDA have a unique combination of properties that make them very attractive for various applications. This unique combination of properties includes low pressure processing (200 psi and below), long term melt stability (several hours at 390.degree. C.), improved toughness, improved solvent resistance, improved adhesive properties, and improved composite mechanical properties.
    Type: Grant
    Filed: February 14, 1995
    Date of Patent: February 2, 1999
    Assignee: The United States of America as represented by the United States National Aeronautics and Space Administration
    Inventor: Brian J. Jensen
  • Patent number: 5859181
    Abstract: A solvent-soluble siloxane polyimide comprising a copolymer obtained by reaction of a diamine compound mixture comprising a diaminopolysiloxane and an alicyclic diamine with an aromatic tetracarboxylic acid anhydride, followed by polyimidization reaction of the resulting polyamic acid forms a heat-resistant adhesive by adding an epoxy resin, a diamine-based curing agent and an organic solvent thereto, The formed adhesives show a distinguished heat-resistant adhesiveness when the resulting siloxane polyimide soluble in ordinary organic solvents is used as a main component of the adhesive for bonding between a base material and a copper foil of a flexible printed substrate. By further addition of a fluorinated resin to the heat-resistant adhesive, the adhesiveness can be more improved.
    Type: Grant
    Filed: December 17, 1997
    Date of Patent: January 12, 1999
    Assignee: Nippon Mektron, Limited
    Inventors: Dong Zhao, Hiroshi Sakuyama, Tomoko Katono, Lin-chiu Chiang, Jeng-Tain Lin
  • Patent number: 5856431
    Abstract: A process for inducing pre-tilt in alignment of a liquid crystal medium comprising exposing at least one optical alignment layer, comprising anisotropically absorbing molecules and hydrophobic moieties, to polarized light; the polarized light having a wavelength within the absorption band of said anisotropically absorbing molecules; wherein the exposed anisotropically absorbing molecules induce alignment of the liquid crystal medium at an angle + and -.theta. with respect to the direction of the polarization of the incident light beam and along the surface of the optical alignment layer, and induce a pre-tilt at an angle .PHI. with respect to the surface of the optical alignment layer and applying a liquid crystal medium to said optical alignment layer, is described. The invention also is directed to liquid crystal display elements made by the process of the invention and to novel polyimide compositions that are useful as optical alignment layers in the invention.
    Type: Grant
    Filed: November 7, 1997
    Date of Patent: January 5, 1999
    Assignee: Alliant Techsystems Inc.
    Inventors: Wayne M. Gibbons, Paul J. Shannon, Shao-Tang Sun
  • Patent number: 5854372
    Abstract: To prepare nitrogen-containing polycondensates, a starting substance which still contains reactive end groups is dispersed in a high-boiling inert solvent, preferably in the presence of a dispersing auxiliary, low molecular weight by-products are distilled off at elevated temperature, the batch is cooled and the dispersed polycondensate is isolated. To prepare the starting substance, a mixture of at least two monomers which react with one another is heated up to a constant reaction temperature, a melt being formed at least in part, but initially no homogeneous melt occurring. The reaction is continued until a homogeneous melt is present. The precondensate formed is then dispersed in the high-boiling inert solvent and the condensation reaction is brought to completion.
    Type: Grant
    Filed: October 5, 1995
    Date of Patent: December 29, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Andree Henze, Karsten Blatter
  • Patent number: 5849397
    Abstract: An aromatic polyimide film in the form of a continuous tape having a thickness of 50 to 125 .mu.m favorably employed for manufacture of electric circuit is composed of a biphenyltetracarboxylic acid recurring unit and a p-phenylenediamine recurring unit. The polyimide film has the following characteristics: a tensile strength of not lower than 30 kg/mm.sup.2 ; a tensile modules of not lower than 500 kg/mm.sup.2 ; a linear expansion coefficient of not higher than 2.5.times.10.sup.-5 cm/cm/.degree.C.; a heat shrinkage ratio of not higher than 0.05%; a low curling having a maximum curling of not higher than 3 mm for a disk of diameter of 86 mm; and a uniform thickness having a maximum rate of inclination of not more than 3 .mu.m per 10 mm.
    Type: Grant
    Filed: October 3, 1996
    Date of Patent: December 15, 1998
    Assignee: Ube Industries, Ltd.
    Inventors: Takashi Kohno, Akinori Otani, Toshinori Hosoma, Hiroshi Inoue
  • Patent number: 5844065
    Abstract: A new diamine, 2,2'-dimethyl-4,4'-bis(4-aminophenoxy)-biphenyl was synthesized and used to prepare high performance engineering plastics by polycondensation. The new diamine as shown in the following formula has a noncoplanar 2,2'-disubstituted biphenylene and a flexible aryl units: ##STR1## The engineering plastics disclosed in the present invention includes polyamides, polyimides and poly(amide-imide)s.
    Type: Grant
    Filed: May 14, 1997
    Date of Patent: December 1, 1998
    Assignee: National Science Council
    Inventors: Der-Jang Liaw, Been-Yang Liaw
  • Patent number: 5834581
    Abstract: A process for making polyimide-polyamic ester copolymer composition comprisingreacting at least one diamine, a pyromellitic diacid diester compound; at least one other tetracarboxylic diacid diester compound and a selected phosphoramide in the presence of a base catalyst to form a polyimide-polyamic acid ester copolymer.
    Type: Grant
    Filed: April 15, 1997
    Date of Patent: November 10, 1998
    Assignee: Olin Microelectronic Chemicals, Inc.
    Inventors: Ahmad Naiini, Steve L. C. Hsu, William D. Weber, Andrew J. Blakeney
  • Patent number: 5830988
    Abstract: Polyetherimide polymers prepared from monomers containing indane moieties are disclosed. The high molecular weight indane polyetherimides are transparent, ductile, and exhibit high glass transition temperatures (>200.degree. C.). In addition, the polyetherimides are thermally stable at high temperatures and exhibit good optical properties making them useful in high temperature processing applications, in the fabrication of optoelectronics devices, and in optical applications.
    Type: Grant
    Filed: August 26, 1997
    Date of Patent: November 3, 1998
    Assignee: Molecular OptoElectronics Corporation
    Inventor: Kwok Pong Chan
  • Patent number: 5820742
    Abstract: An electrodeposition coating method characterized in that in electrodeposition coating of a water soluble composition of a polyimide precursor which is prepared by using 1,2,3,4-butanetetracarboxylic acid or its imide-forming derivative and a diamine and has a percentage of residual acid value of 30 to 3%, there is added previously a water soluble solvent selected from the group consisting of an alcoholic solvent, N-methyl-2-pyrrolidone, dimethylformamide and dimethylacetamide to the above-mentioned composition, and an electrodeposition coating agent used therefor. There can be provided the electrodeposition coating method practicable for the use of a water soluble polyimide composition which is capable of forming a uniform baked coating film having a continuous surface and being excellent in adhesivity to substrate and in toughness.
    Type: Grant
    Filed: May 23, 1996
    Date of Patent: October 13, 1998
    Assignee: Daikin Industries, Ltd.
    Inventors: Shin-i-ti Oda, Toshihide Okamoto, Hiroshi Yokota, Kenjiro Hayashi, Kazufumi Hamabuchi, Toshio Mizuno
  • Patent number: 5821319
    Abstract: A sliding material and a heat resistant filament which primarily comprises a liquid crystal polyimide, a liquid crystal polyamide or a liquid crystal polyamide-imide copolymer having at least one recurring structural unit selected from the formula (1) and the formula (2) and is excellent in heat resistance, mechanical characteristics and other fundamental properties of polyimides, and relates to significant improvement of heat-resistance by heat-treating the sliding material, the filament and the molded items. The liquid crystal polyamide-imide copolymer which comprises in a polymer molecule 0.05.about.0.95 mole ratio of the recurring structural units of the formula (1) and 0.95.about.0.
    Type: Grant
    Filed: April 3, 1996
    Date of Patent: October 13, 1998
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Atsushi Shibuya, Yuichi Okawa, Shoji Tamai, Masahiro Ohta, Akihiro Yamaguchi
  • Patent number: 5817744
    Abstract: The physical properties of high performance composites can be tailored by using blends to make the composites. The resulting composites are relatively easy to make and have long-term, high performance capabilities even in harsh service conditions. The blends of the present invention include at least one oligomer having an aromatic, aliphatic, or mixed aromatic and aliphatic backbone from one chemical family and an unsaturated hydrocarbon end cap and at least one polymer from a different chemical family. Upon curing, the oligomer in the blend addition polymerize to form composites possessing advanced properties with respect to those exhibited by the pure oligomer or the pure polymer. Coreactive oligomer blends can be used instead of a pure oligomer to form composites that include addition polymers, block copolymers, and the compatible polymer, thereby further achieving a tailoring of properties in the cured composite. The blends can be prepregged and cured to form composites.
    Type: Grant
    Filed: February 14, 1997
    Date of Patent: October 6, 1998
    Assignee: The Boeing Company
    Inventors: Clyde H. Sheppard, Hyman R. Lubowitz
  • Patent number: 5817741
    Abstract: A diamine which is useful in preparing a new flexible polyamide and polyimide with an aromatic dicarboxylic acid and a tetracarboxylic dianhydrides, respectively, has a general formula as follows: ##STR1## wherein R.sub.1 is a proton (--H) or methyl (--CH.sub.3) and n is an integer ranging from 1 to 4. These polyamide and polyimide exhibit good mechanical performance and processability.
    Type: Grant
    Filed: May 14, 1997
    Date of Patent: October 6, 1998
    Assignee: National Science Council
    Inventors: Der-Jang Liaw, Been-Yang Liaw
  • Patent number: 5807961
    Abstract: This invention is directed to a polyimide film useful as use applications for electronic materials; a liquid crystal aligning film using the same; a liquid crystal display element provided with the liquid crystal aligning film; and a polyamic acid used as a raw material of the polyimide constituting the polyimide film.The polyimide used for preparing the above polyimide films, consists of a diamine component, the 50% by mol or more based upon the total diamine, of which is a diamine having a core structure having no polar group such as 1,2-bis(4-(4-aminobenzyl)phenyl)ethane, 1,6-bis(4-(4-aminobenzyl)phenyl)hexane, 1,1-bis(4-(4-aminobenzyl)phenyl)heptane, etc., and a tetracarboxylic acid dianhydride, and if necessary, an aminosilicon compound, is used as a liquid crystal aligning film.
    Type: Grant
    Filed: June 20, 1997
    Date of Patent: September 15, 1998
    Assignee: Chisso Corporation
    Inventors: Toshiya Sawai, Masaaki Yazawa, Seiji Oikawa, Shizuo Murata, Masaharu Hayakawa, Etsuo Nakagawa
  • Patent number: 5789524
    Abstract: A process for producing a polyimide composition by reacting at least one polyamic acid or at least one polyamic ester or a mixture of at least one polyamic acid and at least one polyamic ester with a selected phosphoramide in the presence of at least one base catalyst to from a polyimide composition.
    Type: Grant
    Filed: April 15, 1997
    Date of Patent: August 4, 1998
    Assignee: Olin Microelectronic Chemicals, Inc.
    Inventors: Steve L. C. Hsu, Ahmad Naiini, William D. Weber, Andrew J. Blakeney
  • Patent number: 5789525
    Abstract: A process for making polyimide composition comprising reacting at least one diamine, at least one tetracarboxylic diacid diester, selected phosphoramide and at least one base catalyst to form at least one polyimide compound, said reaction carried out at a temperature from about 20.degree. C. to about 60.degree. C. and wherein the molar ratio of diamine:tetracarboxylic diacid diester:phosphoramide:base catalyst is in the range of 0.8-1.2:1:2.5-4.0:2.5-4.0.
    Type: Grant
    Filed: April 15, 1997
    Date of Patent: August 4, 1998
    Assignee: Olin Microelectronic Chemicals, Inc.
    Inventors: Ahmad Naiini, Steve L. C. Hsu, William D. Weber, Andrew J. Blakeney
  • Patent number: 5783656
    Abstract: There are provided a polyamic acid obtainable by reacting a diamine compound of the formula (1) ##STR1## wherein R.sup.1 is an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms or a halogen atom, each of X and Y is independently a divalent linking group,with a tetracarboxylic acid dianhydride; a polyimide obtainable by dehydrating and ring-closing the above polyamic acid; and a liquid crystal aligning agent containing the above polyamic acid and/or the above polyimide.
    Type: Grant
    Filed: January 31, 1997
    Date of Patent: July 21, 1998
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Masayuki Kimura, Tsukasa Toyoshima, Keiichi Yamamoto, Kengo Wakabayashi, Yasuo Matsuki, Kyouyu Yasuda
  • Patent number: 5780556
    Abstract: The present invention provides an amino curable polyester oligomer composition having low viscosity and a narrow molecular weight distribution comprising one or a mixture of oligomers (a) and (b): ##STR1## wherein R is the residue of at least one aliphatic, cycloaliphatic or mixed aliphatic/aromatic polycarboxylic-acid having from 2 to about 20 carbon atoms, R.sub.1 is the residue of at least one aliphatic, cycloaliphatic or mixed aliphatic/cycloaliphatic polyol having from 2 to about 20 carbon atoms, A is a radical of the formula: ##STR2## B is a radical of the formula: ##STR3## wherein R.sub.4 is H, OH, halogen or an organic radical containing 1 to 4 carbon atoms, R.sub.5 is a direct bond or an organic radical containing 1 to 20 carbon atoms and R.sub.6 is an organic radical containing 2 to 20 carbon atoms, n is a number averaging from greater than 0 up to less than 2 and p is a number averaging from about 0.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 14, 1998
    Assignee: Exxon Chemical Patents Inc
    Inventors: Albert Ilya Yezrielev, Konstantinos R. Rigopoulos, Vijay Swarup
  • Patent number: 5777068
    Abstract: Provided are photosensitive resin compositions comprising a polyamic compound having, at each terminal thereof, a specific actinic ray-sensitive functional group which has substituent groups each having a photopolymerizable carbon-carbon double bond, a photosensitive auxiliary having a photopolymerizable functional group and a solvent. The photosensitive resin compositions of the invention are excellent in resist properties such as sensitivity and good in storage stability and can provide a film small in residual stress.
    Type: Grant
    Filed: September 12, 1995
    Date of Patent: July 7, 1998
    Assignees: Nippon Zeon Co., Ltd., Fujitsu Limited
    Inventors: Akira Tanaka, Satoshi Tazaki, Kei Sakamoto, Yasuhiro Yoneda, Kishio Yokouchi, Daisuke Mizutani, Yoshikatsu Ishizuki
  • Patent number: 5773561
    Abstract: The present invention relates generally to a new adhesive comprising a vinyl containing siloxane-containing polyimide for use in TSM capping of electronic package assemblies with adhesive capability of providing a seal band width of less than 4mm and even less than 2mm, solubility in non-toxic and environmentally safe solvents and durable adhesive properties and to a method for making the polyimides, a method for using the polyimides to make electronic packages and electronic packages made using the adhesive. The preferred vinyl-containing siloxane containing polyimide is a block type polymer containing blocks of a dianhydride-aromatic diamine oligomeric reaction product joined by non-vinyl/vinyl containing siloxane diamine forming links.
    Type: Grant
    Filed: August 2, 1996
    Date of Patent: June 30, 1998
    Assignee: International Business Machines Corporation
    Inventors: Krishna Gandhi Sachdev, Michael Berger, Patrick A. Coico, Frank L. Pompeo
  • Patent number: 5773553
    Abstract: Disclosed is a process which comprises reacting a polyimide precursor with borane. Also disclosed is a thermal ink jet printhead containing a layer comprising the product of this reaction.
    Type: Grant
    Filed: June 13, 1996
    Date of Patent: June 30, 1998
    Assignee: Xerox Corporation
    Inventors: Timothy J. Fuller, Ram S. Narang
  • Patent number: 5770676
    Abstract: In the process of the present invention, a non-polar, aprotic solvent is removed from an oligomer/polymer solution by freeze-drying in order to produce IPNs and semi-IPNs. By thermally quenching the solution to a solid in a short length of time, the size of the minor constituent-rich regions is greatly reduced as they are excluded along with the major constituent from the regions of crystallizing solvent. The use of this process sequence of controlling phase morphology provides IPNs and semi-IPNs with improved fracture toughness, microcracking resistance, and other physical-mechanical properties as compared to IPNs and semi-IPNs formed when the solvent is evaporated rather than sublimed.
    Type: Grant
    Filed: April 10, 1996
    Date of Patent: June 23, 1998
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Ruth H. Pater, Marion G. Hansen
  • Patent number: 5760168
    Abstract: Controlled molecular weight phenylethynyl terminated imide oligomers (PETIs) have been prepared by the cyclodehydration of precursor phenylethynyl terminated amic acid oligomers. Amino terminated amic acid oligomers are prepared from the reaction of dianhydride(s) with an excess of diamine(s) and subsequently endcapped with phenylethynyl phthalic anhydride(s) (PEPA). The polymerizations are carried out in polar aprotic solvents such as N-methyl-2-pyrrolidinone or N,N-dimethylacetamide under nitrogen at room temperature. The amic acid oligomers are subsequently cyclodehydrated either thermally or chemically to the corresponding imide oligomers. Direct preparation of PETIs from the reaction of dianhydride(s) with an excess of diamine(s) and endcapped with phenylethynyl phthalic anhydride(s) has been performed in m-cresol. Phenylethynyl phthalic anhydrides are synthesized by the palladium catalyzed reaction of phenylacetylene with bromo substituted phthalic anhydrides in triethylamine.
    Type: Grant
    Filed: October 21, 1996
    Date of Patent: June 2, 1998
    Assignee: The United States of America as represented by the Administrator of the National Aeuonautics and Space Administration
    Inventors: Paul M. Hergenrother, Joesph G. Smith, Jr.
  • Patent number: 5756648
    Abstract: Photosensitive polyimides (Ps-PIM) materials have been synthesized that belong to three families of Ps-PIM materials. Through the use of precursors, various catalytic compositions with differing photosensitivities are provided. The results are Ps-PIM materials having increased photosensitivities at wavelengths longer than approximately 330 to 350 nm and an associated catalytic system that is insensitive to oxygen. A variety of applications, including use in holographic systems, are improved by the present invention.
    Type: Grant
    Filed: October 25, 1995
    Date of Patent: May 26, 1998
    Assignee: Tamarack Storage Devices, Inc.
    Inventor: Chung J. Lee
  • Patent number: 5756650
    Abstract: A polyimide precursor composition, which comprises, a polyamic acid having a repeating unit represented by the following general formula (PA), and at least one kinds of cure accelerator selected from the group consisting of a substituted or unsubstituted nitrogen-containing heterocyclic compound exhibiting an acid dissociation index "pKa" of a proton complex ranging from 0 to 8 in an aqueous solution thereof, or an N-oxide compound of said nitrogen-containing heterocyclic compound (AC1), a substituted or unsubstituted amino acid compound (AC2), and an aromatic hydrocarbon compound or an aromatic heterocyclic compound having a molecular weight of 1,000 or less and two or more hydroxyl groups (AC3): ##STR1## wherein .phi. is a quadrivalent organic group, .phi. is a bivalent organic group, R is a substituted or unsubstituted hydrocarbon group, organosilicic group or hydrogen atom.
    Type: Grant
    Filed: March 13, 1997
    Date of Patent: May 26, 1998
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Yoshiaki Kawamonzen, Masayuki Oba, Satoshi Mikoshiba, Shigeru Matake
  • Patent number: 5756649
    Abstract: A liquid crystal aligning agent comprising a polyamic acid containing an aliphatic and/or alicyclic hydrocarbon group and a polyimide containing an aliphatic and/or alicyclic hydrocarbon group; and a liquid crystal display device using the liquid crystal aligning agent. This liquid crystal aligning agent gives a liquid crystal aligning film which has good liquid crystal aligning property and in which pretilt angle can be changed by radiation with a small energy and which is suitable for domain-divided alignment type liquid crystal display having a wide view angle.
    Type: Grant
    Filed: January 28, 1997
    Date of Patent: May 26, 1998
    Assignees: Japan Synthetic Rubber Co., Ltd., Sharp Corporation
    Inventors: Shigeaki Mizushima, Noriko Watanabe, Hiroko Iwagoe, Seiji Makino, Sigeo Kawamura, Yusuke Tsuda, Nobuo Bessho
  • Patent number: 5750641
    Abstract: An angularity enhancement layer in a liquid crystal display, which display comprises a liquid crystal cell, wherein the angularity enhancement layer includes a negative birefringent polyimide layer comprising a plurality of structural units having pendant fluorene groups, said angularity enhancement layer being disposed on at least one surface of said liquid crystal cell. A liquid crystal display can comprise an angularity enhancement construction of the invention which comprises a polyimide layer.
    Type: Grant
    Filed: May 23, 1996
    Date of Patent: May 12, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Stephen A. Ezzell, Hassan Sahouani, Ernest L. Thurber
  • Patent number: 5750633
    Abstract: A dope for cast formation comprising a fluorine including polyimide resin and an organic solvent (P) as main components. The fluorine including polyimide resin has at least one --CF.sub.3 group in the repeating molecular unit. The organic solvent (P) is present during the resin polymerization of the fluorine including polyimide resin. The organic solvent (P) is diethylene glycol dimethyl ether.
    Type: Grant
    Filed: October 24, 1995
    Date of Patent: May 12, 1998
    Assignee: Nitto Denko Corporation
    Inventors: Tomomi Ohara, Hisao Hachisuka
  • Patent number: 5747175
    Abstract: Liquid-crystalline polymer blends comprising two or more cholesteric liquid-crystalline polymers or at least one nematic liquid-crystalline polymer and at least one cholesteric liquid-crystalline polymer.All hues can be produced specifically and in a reproducible manner by variation in the blend components and in the mixing ratio. The polymer blends are suitable as materials or as effect pigments.
    Type: Grant
    Filed: April 1, 1997
    Date of Patent: May 5, 1998
    Inventors: Erwin Dietz, Axel Schonfeld
  • Patent number: 5744575
    Abstract: An aromatic polyimide having a recurring unit of the formula (I): ##STR1## wherein Ar is a divalent aromatic group having one or two benzene rings which has a sulfonate group of --SO.sub.3 H, --SO.sub.3 M, and --SO.sub.3 N(L).sub.4 on the ring, wherein M is an alkali metal and L is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, is favorably employed in the form of a semipermeable film for gas separation.
    Type: Grant
    Filed: June 6, 1996
    Date of Patent: April 28, 1998
    Assignee: Ube Industries, Ltd.
    Inventors: Shunsuke Nakanishi, Kenji Ito, Yoshihiro Kusuki
  • Patent number: 5741883
    Abstract: Tough, soluble, aromatic, thermoplastic copolyimides were prepared by reacting 4,4'-oxydiphthalic anhydride, 3,4,3',4'-biphenyltetracarboxylic dianhydride and 3,4'-oxydianiline. These copolyimides were found to be soluble in common amide solvents such as N,N'-dimethyl acetamide, N-methylpyrrolidinone, and dimethylformamide allowing them to be applied as the fully imidized copolymer and to be used to prepare a wide range of articles.
    Type: Grant
    Filed: December 16, 1994
    Date of Patent: April 21, 1998
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Robert G. Bryant
  • Patent number: 5739263
    Abstract: The present invention provides a film adhesive comprising, as the main constituent, a polyimide resin having a glass transition temperature of 350.degree. C. or lower and soluble in organic solvents, which polyimide resin is obtained by reacting at least one of the following acid components (A) and (B)(A) 4,4'-oxydiphthalic acid dianhydride(B) 3,3',4,4'-biphenyltetracarboxylic acid dianhydride and/or 3,3',4,4'-benzophenonetetracarboxylic acid dianhydridewith at least one of the following amine components (C) and (D)(C) a siloxane compound represented by the following general formula (1) and/or 2,2-bis(4-(4-amino-phenoxy)phenyl)propane ##STR1## wherein R.sub.1 and R.sub.2 are each a bivalent aliphatic (C.sub.1-4) or aromatic group; R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each a mono-valent aliphatic or aromatic group; and k is an integer of 1-20,(D) bis(aminophenoxy)benzene and/or dimethylphenylene-diamineto give rise to ring closure of imide, as well as a process for producing said film adhesive.
    Type: Grant
    Filed: January 28, 1994
    Date of Patent: April 14, 1998
    Assignee: Sumitomo Bakelite Company Limited
    Inventors: Tatsuhiro Yoshida, Yoshitaka Okugawa, Toshio Suzuki, Toshiro Takeda, Yushi Sakamoto, Takuya Tochimoto
  • Patent number: 5734008
    Abstract: The polyimide film of this invention is formed from a polyimide, which is prepared by reacting a diamino compound represented by the general formula (1): ##STR1## wherein X represents a hydrocarbon group having 1 to 20 carbon atoms or a sulfur atom; R represents each independently a halogen atom, a hydrocarbon group having 1 to 6 carbon atoms or a halogen-containing hydrocarbon group having 1 to 6 carbon atoms; a represents each independently an integer of 0 to 4;with a tetracarboxylic dianhydride represented by the general formula (2) ##STR2## wherein Y represents a tetravalent organic group having 2 or more carbon atoms.The polyimide film obtained can be applied favorably to a flexible printed circuit board without adhesion layer, a protective coating for electronic parts and electric wires, or a heat resistant adhesive.
    Type: Grant
    Filed: October 23, 1995
    Date of Patent: March 31, 1998
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mika Shirasaki, Youichi Ueda, Mitsuhiro Shibata
  • Patent number: 5731405
    Abstract: A process for inducing pre-tilt in alignment of a liquid crystal medium comprising exposing at least one optical alignment layer, comprising anisotropically absorbing molecules and hydrophobic moieties, to polarized light; the polarized light having a wavelength within the absorption band of said anisotropically absorbing molecules; wherein the exposed anisotropically absorbing molecules induce alignment of the liquid crystal medium at an angle + and -.theta. with respect to the direction of the polarization of the incident light beam and along the surface of the optical alignment layer, and induce a pre-tilt at an angle .PHI. with respect to the surface of the optical alignment layer and applying a liquid crystal medium to said optical alignment layer, is described. The invention also is directed to liquid crystal display elements made by the process of the invention and to novel polyimide compositions that are useful as optical alignment layers in the invention.
    Type: Grant
    Filed: March 29, 1996
    Date of Patent: March 24, 1998
    Assignee: Alliant Techsystems Inc.
    Inventors: Wayne M. Gibbons, Paul J. Shannon, Shao-Tang Sun
  • Patent number: 5731404
    Abstract: A polyimide alignment film based on pyromellitic dianhydride and a bis(4-aminophenoxy) aromatic compound, such as 1,3-bis(4-aminophenoxy)benzene or 1,4-bis(4-aminophenoxy)benzene, providing low tilt angles of from to 2 degrees when used in liquid crystal displays.
    Type: Grant
    Filed: November 1, 1995
    Date of Patent: March 24, 1998
    Assignees: E. I. du Pont de Nemours and Company, Merck Patent GmbH
    Inventors: Brian Carl Auman, Edgar Bohm
  • Patent number: 5723571
    Abstract: A novel polyimide is soluble in organic solvents and excels in heat resistance. The polyimide comprises 95-40 mol % of the repeating unit represented by the formulas (1) and 60-5 mol % of the repeating unit represented by the formula (2) and has a number average molecular weight of 4,000-200,000: ##STR1## wherein X is --SO.sub.2 -- and/or --C(.dbd.O)--OCH.sub.2 CH.sub.2 O--C(.dbd.O)--, Ar is a divalent group containing aromatic rings, and R is an alkylene group having 1-10 carbon atoms or a group: --CH.sub.2 OC.sub.6 H.sub.4 --, and n is an integer of 1-20.
    Type: Grant
    Filed: August 29, 1996
    Date of Patent: March 3, 1998
    Assignee: Tomoegawa Paper Co., Ltd.
    Inventors: Osamu Oka, Takeshi Nishigaya
  • Patent number: 5719253
    Abstract: This invention provides a poly(amic acid) solution which does not contain aprotic polar solvents such as DMF, NMP, DMAc, DMSO, as well as a polyimide film obtained therefrom having appropriate flexibility and a small coefficient of linear thermal expansion and a coated material in which the polyimide film is formed on a substrate.More particularly, it provides a poly(amic acid) solution which has an aromatic poly(amic acid) and a tertiary amine as the solute and a water soluble alcohol compound and/or a water soluble ether compound as the solvent and contains substantially no aprotic polar solvent, as well as a polyimide film obtained from the poly(amic acid) solution and a coated material obtained by forming the film on a substrate.
    Type: Grant
    Filed: October 5, 1995
    Date of Patent: February 17, 1998
    Assignee: Unitika Ltd.
    Inventors: Yoshiaki Echigo, Shoji Okamoto, Hiroshi Yamada, Isao Tomioka, Yoshiaki Iwaya
  • Patent number: 5714566
    Abstract: Thermomechanical and thermo-oxidative stabilities in resin composites across the range of aerospace "engineering thermoplastic" resins are improved by forming four crosslinks at each addition polymerization site in the backbone of the resin using crosslinking functionalities of the general formula: ##STR1## in the oligomers, wherein Z= ##STR2## .beta.=the residue an organic radical selected from the group consisting of: ##STR3## --O--.O slashed.--COOH, --O--.O slashed.--COX, --X, --O.paren open-st.(R.sub.8 .paren close-st.OH, ##STR4## --O--.O slashed.--NH.sub.2 ; E= ##STR5## R.sub.8 =a divalent organic radical; X=halogen;Me=methylT=allyl or methallyl.G=--CH.sub.2 --, --S--, --CO--, --SO--, --O--, --CHR.sub.3 --, or --C(R.sub.3).sub.2 --;i=1 or 2;R.sub.3 =hydrogen, lower alkyl, lower alkoxy, aryl, or aryloxy; and.THETA.=--C.tbd.N; --O--C.tbd.N, --S--C.tbd.N, or --CR.sub.3 .dbd.C(R.sub.3).sub.2.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: February 3, 1998
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowtiz, Clyde H. Sheppard
  • Patent number: 5714572
    Abstract: The present invention provides a polyimide resin composition comprising:(a) a polyamide resin comprising a repeating unit represented by the general formula (1): ##STR1## wherein X represents a tetravalent organic group represented by the formula (2): ##STR2## Y represents a divalent organic group comprising a divalent siloxane residual group represented by the formula (3): ##STR3## wherein m is an integer of 60 to 120; and a divalent aromatic group represented by the formula (4): ##STR4## wherein R.sup.1 represents a hydrogen atom or a fluorine atom; and (B) cyclohexanone. From this composition, polyimide resin films can be obtained by heating at a lower temperature for a short time, and the films obtained show good adhesion under moisture-resistant conditions.
    Type: Grant
    Filed: October 23, 1996
    Date of Patent: February 3, 1998
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventor: Hideto Kato