Nitrogen-containing Compound Is A Reactant Other Than Wherein Nitrogen Is Solely Present As A Carboxylic Acid Derivative Patents (Class 528/172)
  • Patent number: 7074882
    Abstract: The present invention provides a polyimide resin for an electrical insulating material which comprises a polyimide resin having a repeating unit represented by general formula (I): wherein R1 represents a bivalent organic group.
    Type: Grant
    Filed: July 2, 2004
    Date of Patent: July 11, 2006
    Assignee: Nitto Denko Corporation
    Inventors: Takami Hikita, Hisae Sugihara, Amane Mochizuki
  • Patent number: 7074880
    Abstract: A preparation process of polyimide aerogels that composed of aromatic dianhydrides and aromatic diamines or a combined aromatic and aliphatic diamines is described. Also descried is a process to produce carbon aerogels derived from polyimide aerogel composed of a rigid aromatic diamine and an aromatic dianhydride. Finally, the processes to produce carbon aerogels or xerogel-aerogel hybrid, both of which impregnated with highly dispersed transition metal clusters, and metal carbide aerogels, deriving from the polyimide aerogels composed of a rigid aromatic diamine and an aromatic dianhydride, are described. The polyimide aerogels and the polyimide aerogel derivatives consist of interconnecting mesopores with average pore size at 10 to 30 nm and a mono-dispersed pore size distribution. The gel density could be as low as 0.008 g/cc and accessible surface area as high as 1300 m2/g.
    Type: Grant
    Filed: July 22, 2003
    Date of Patent: July 11, 2006
    Assignee: Aspen Aerogels, Inc.
    Inventors: Wendell Rhine, Jing Wang, Redouane Begag
  • Patent number: 7071282
    Abstract: Disclosed herein are polyetherimide compositions comprising structural units of the formula: derived from at least one benzimidazole diamine, wherein R1 and R2 are independently selected from hydrogen and C1–C6 alkyl groups; “A” comprises structural units of the formulae: or mixtures of the foregoing structural units; wherein “D” is a divalent aromatic group, R3 and R10–R12 are independently selected from hydrogen, halogen, and C1–C6 alkyl groups; “q” is an integer having a value of 1 up to the number of positions available on the aromatic ring for substitution; and “W” is a linking group; and “B” comprises substituted and unsubstituted arylene groups having from about 6 to about 25 carbon atoms. Methods for producing the polyetherimide compositions are also disclosed herein.
    Type: Grant
    Filed: June 3, 2003
    Date of Patent: July 4, 2006
    Assignee: General Electric Company
    Inventors: Havva Acar, Daniel Joseph Brunelle
  • Patent number: 7053168
    Abstract: A method for preparing a polyimide includes introducing a mixture of an oligomer and a solvent to an extruder, removing solvent via at least one extruder vent, and melt kneading the oligomer to form a polyimide. The polyimide has a low residual solvent content. The method is faster than solution polymerization of polyimides, and it avoids the stoichiometric inaccuracies associated with reactive extrusion processes that use monomers as starting materials.
    Type: Grant
    Filed: October 10, 2003
    Date of Patent: May 30, 2006
    Assignee: General Electric Company
    Inventors: Norberto Silvi, Mark Howard Giammattei, Paul Edward Howson, Farid Fouad Khouri
  • Patent number: 7041773
    Abstract: Polyimide sulfone resins are provided with a glass transition temperature of from 200–350° C., residual volatile species concentration of less than 500 ppm and a total reactive end group concentration of less than about 120 milliequivalents/kilogram resin. The resins have high heat capability and good melt stability. Methods to prepare the said resins and articles made from the resins are also provided.
    Type: Grant
    Filed: September 26, 2003
    Date of Patent: May 9, 2006
    Assignee: General Electric Company
    Inventors: Robert R Gallucci, Roy Ray Odle
  • Patent number: 7041778
    Abstract: A novel polyimide resin consisting essentially of 3,3?,4,4?-benzophenonetetracarboxylic dianhydride (BTDA), 3,4,3?,4?-biphenyltetracarboxylic dianhydride (BPDA), 2,2 bis (3?,4?-dicarboxy phenyl) hexafluoro propane dianhydride (6FDA), 2-(3,4-dicarboxyphenyl)-1-phenylacetylene anhydride (4-PEPA) and an aromatic diamine.
    Type: Grant
    Filed: May 18, 2004
    Date of Patent: May 9, 2006
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: David B. Curliss, Jason E. Lincoln, Katie E. Thorp
  • Patent number: 7026436
    Abstract: The present invention relates to a polyimide adhesive composition having a polyimide derived from an aromatic dianhydride and a diamine component, where the diamine component is preferably about 50 to 90 mole % of an aliphatic diamine and about 10 to 50 mole % of an aromatic diamine. In one embodiment, the aliphatic diamine has the structural formula H2N—R—NH2 wherein R is hydrocarbon from C4 to C16 and the polyimide adhesive has a glass transition temperature in the range of from 150° C. to 200° C. The present invention also relates to compositions comprising the polyimide adhesive of the present invention, including polyimide metal-clad laminate useful as flexible circuit when metal traces are formed out of the metal used in flexible, rigid, or flex-rigid circuit applications.
    Type: Grant
    Filed: November 26, 2002
    Date of Patent: April 11, 2006
    Assignee: E.I. du Pont de Nemours and Company
    Inventor: Kuppusamy Kanakarajan
  • Patent number: 7022809
    Abstract: The present invention relates to novel polyimides derived from 6FDA and from 3,3-dihydroxy-4,4?-diaminobiphenyl and novel polyimides derived from PMDA and from Bis-AP-AF, having alkyl, arylalkyl, heteroarylalkyl, (cycloalkyl)alkyl, fluoroalkyl or siloxane side groups. The present invention also relates to a method of producing nematic liquid-crystal devices, which comprises the steps consisting in: depositing one of the polyimides according to the invention on a substrate; annealing the polyimide in one or more steps; and defining an azimuthal orientation of the polyimide coating.
    Type: Grant
    Filed: May 30, 2002
    Date of Patent: April 4, 2006
    Assignee: Nemoptic
    Inventors: Sandrine Lamarque, Jean-Claude Dubois, Didier Gallaire
  • Patent number: 7022810
    Abstract: A new class of hybrid organic-inorganic materials, and methods of synthesis, that can be used as a proton exchange membrane in a direct methanol fuel cell. In contrast with Nafion® PEM materials, which have random sulfonation, the new class of materials have ordered sulfonation achieved through self-assembly of alternating polyimide segments of different molecular weights comprising, for example, highly sulfonated hydrophilic PDA-DASA polyimide segment alternating with an unsulfonated hydrophobic 6FDA-DAS polyimide segment. An inorganic phase, e.g., 0.5–5 wt % TEOS, can be incorporated in the sulfonated polyimide copolymer to further improve its properties. The new materials exhibit reduced swelling when exposed to water, increased thermal stability, and decreased O2 and H2 gas permeability, while retaining proton conductivities similar to Nafion®. These improved properties may allow direct methanol fuel cells to operate at higher temperatures and with higher efficiencies due to reduced methanol crossover.
    Type: Grant
    Filed: December 18, 2003
    Date of Patent: April 4, 2006
    Assignee: Sandia Corporation
    Inventor: Christopher J. Cornelius
  • Patent number: 7019103
    Abstract: A terminal-crosslinkable polyamic acid oligomer having 1) heat resistance indicated by Tg of 300° C. or more and a pyrolysis temperature of 500° C. or more, 2) toughness, and 3) capability of allowing an increase in concentration. The polyamic acid oligomer is obtained by reacting an aromatic tetracarboxylic dianhydride including 2,2?,3,3?-biphenyltetracarboxylic dianhydride, an aromatic diamine compound, and a reactive crosslinking agent including an amino group or acid anhydride group and a crosslinkable group in the molecule, and includes a crosslinkable group at the molecular terminal.
    Type: Grant
    Filed: May 5, 2004
    Date of Patent: March 28, 2006
    Assignees: JSR Corporation, Ube Industries, Ltd.
    Inventors: Rikio Yokota, Kohei Goto, Hideki Ozawa
  • Patent number: 7015304
    Abstract: This invention relates to the composition and a solvent-free process for preparing novel imide oligomers and polymers specifically formulated with effective amounts of a dianhydride such as 2,3,3?,4-biphenyltetra carboxylic dianydride (a-BPDA), at least one aromatic diamine and an endcapped of 4-phenylethynylphthalic anhydride (PEPA) or nadic anhydride to produce imide oligomers that possess a low-melt viscosity of 1–60 poise at 260–280° C. When the imide oligomer melt is cured at about 371° C. in a press or autoclave under 100–500 psi, the melt resulted in a thermoset polyimide having a glass transition temperature (Tg) equal to and above 310° C. A novel feature of this process is that the monomers; namely the dianhydrides, diamines and the endcaps, are melt processable to form imide oligomers at temperatures ranging between 232–280° C. (450–535° F.) without any solvent.
    Type: Grant
    Filed: July 23, 2004
    Date of Patent: March 21, 2006
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Chun-Hua Chuang
  • Patent number: 7005165
    Abstract: The present invention provides novel polyamic acids and polyimide optical alignment layers for inducing alignment of a liquid crystal medium. The novel compositions comprise reactive diamines containing a C3–C20 linear or branched hydrocarbon chains containing 1 to 4 carbon—carbon double bonds. The invention further describes liquid crystal displays comprising the novel polyimide optical alignment layers.
    Type: Grant
    Filed: December 19, 2000
    Date of Patent: February 28, 2006
    Assignee: Elsicon, Inc.
    Inventors: Wayne M. Gibbons, Patricia A. Rose, Paul J. Shannon, Hanxing Zheng
  • Patent number: 7001606
    Abstract: The invention relates to biocidal polymers based on guanidine salts characterized in that they are representatives of a number of polyoxyalkylene guanidines and their salts and are a product of a polycondensation of guanidine salts with diamines which include two amino groups and polyoxyalkylene chains therebetween. In addition to a high bactericidity, these new polymer products are provided with a relatively low toxicity, an increased hydrophily, a quick and complete dilution in water, increased values of relative molar mass, and distinct characteristics of polymer surface active substances.
    Type: Grant
    Filed: May 8, 2001
    Date of Patent: February 21, 2006
    Assignee: P.O.C. Oil Industry Technology Beratungsges m.b.H.
    Inventors: Oskar J. Schmidt, Andreas Schmidt, Dimitri Toptchiev
  • Patent number: 6991834
    Abstract: The present invention provides novel polyamic acids and polyimide optical alignment layers for inducing alignment of a liquid crystal medium. The novel compositions comprise crosslinking diamines containing a C3–C22 linear or branched hydrocarbon chains containing 1 to 4 carbon—carbon double bonds. The invention further describes liquid crystal displays comprising the novel polyimide optical alignment layers.
    Type: Grant
    Filed: October 15, 2002
    Date of Patent: January 31, 2006
    Assignee: Elsicon, Inc.
    Inventors: Wayne M. Gibbons, Patricia A. Rose, Paul J. Shannon, Hanxing Zheng
  • Patent number: 6992165
    Abstract: A method for making an amine-terminated polyarylene polyether thermoplastic in which a liquid/solid slurry reaction mixture is formed in an oxygen-free atmosphere. The reaction mixture is composed of a dihydroxyaromatic compound, a dihaloaromatic compound, an amino-hydroxyaromatic compound, a weak base, an aprotic polar solvent and a non-aromatic azeotrope former which is substantially imiscible with the aprotic polar solvent, said azeotrope former consisting of a molecule which has from 6 to 10 carbon atoms. The reaction mixture is refluxed at an elevated temperature to eventually produce a solution of the amine-terminated polyarylene polyether in the polar solvent. The method is designed for use in producing large amounts of thermoplastic in a simple, efficient and reliable manner.
    Type: Grant
    Filed: December 17, 2003
    Date of Patent: January 31, 2006
    Assignee: HEXCEL Corporation
    Inventor: Winston Lee Hedges
  • Patent number: 6987163
    Abstract: The invention relates to a modified polybenzimidazole (PBI), membranes that are fabricated from these polymers, and their use in electrochemical applications. These membranes have high ionic conductivity and are suitable for solid polymer electrolytes in electrochemical applications, especially for high temperature polymer electrolyte membrane (PEM) fuel cells.
    Type: Grant
    Filed: August 7, 2002
    Date of Patent: January 17, 2006
    Assignee: Research Foundation of the State University of New York
    Inventors: Israel Cabasso, Youxin Yuan, Frederick E. Johnson
  • Patent number: 6984714
    Abstract: This invention relates to a siloxane-modified polyimide resin which shows excellent adhesiveness and can be bonded by thermocompression at high temperature even after subjection to thermal hysteresis in the manufacturing step for electronic parts. This polyimide resin is obtained from an aromatic tetracarboxylic acid dianhydride (A) and a diamine (B) comprising 30–95 mol % of a bis(4-aminophenoxy)alkane (B1) and 5–70 mol % of a siloxanediamine (B2) as essential components.
    Type: Grant
    Filed: April 23, 2003
    Date of Patent: January 10, 2006
    Assignee: Nippon Steel Chemical Co., Ltd.
    Inventors: Kiwamu Tokuhisa, Hongyuan Wang
  • Patent number: 6979721
    Abstract: This invention relates to polyimides having improved thermal-oxidative stability, to the process of preparing said polyimides, and the use of polyimide prepolymers in the preparation of prepregs and composites. The polyimides are particularly useful in the preparation of fiber-reinforced, high-temperature composites for use in various engine parts including inlets, fan ducts, exit flaps and other parts of high speed aircraft.
    Type: Grant
    Filed: October 23, 2003
    Date of Patent: December 27, 2005
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Mary Ann B. Meador, Aryeh A. Frimer
  • Patent number: 6956098
    Abstract: The substrates of the present invention comprise a polyimide base polymer derived at least in part from collinear monomers together with crankshaft monomers. The resulting polyimide material has been found to provide advantageous properties, particularly for electronics type applications.
    Type: Grant
    Filed: September 20, 2002
    Date of Patent: October 18, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: John Donald Summers, Richard Frederich Sutton, Jr., Brian Carl Auman
  • Patent number: 6949618
    Abstract: Provided are polyimide and a thin film thereof which have a three-dimensional structure and therefore are excellent in a mechanical strength and a heat resistance as compared with those of conventional linear polyimide. The polyimide is obtained from a salt of multifunctional amine represented by Formula (1): (wherein A represents a tetravalent organic group, and n represents an integer of 0 to 3) and tetracarboxylic diester represented by Formula (2): (wherein B represents a tetravalent organic group having 1 to 20 carbon atoms, and R1 and R2 each represent independently an alkyl group having 1 to 5 carbon atoms).
    Type: Grant
    Filed: October 29, 2002
    Date of Patent: September 27, 2005
    Assignee: Chisso Corporation
    Inventor: Takashi Kato
  • Patent number: 6949619
    Abstract: A polyimide resin having phenolic hydroxyl radicals in its skeleton is prepared using a diamine bearing an aromatic ring having an amino radical attached thereto and another aromatic ring having a phenolic hydroxyl radical. The polyimide resin and a composition comprising the polyimide resin, an epoxy resin and a curing agent are suited for use as varnish, adhesive and adhesive film for which adhesion and heat resistance are required.
    Type: Grant
    Filed: July 18, 2003
    Date of Patent: September 27, 2005
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Nobuhiro Ichiroku, Masachika Yoshino, Hideki Akiba, Toshio Shiobara
  • Patent number: 6927274
    Abstract: Polyimide precursors contained in resin compositions of the present invention have a polymer structure unit represented by formula (1) below: wherein chemical structure A2 includes an alicyclic compound but not an aromatic compound such as a benzene ring so that they provide excellent light transmission over a wide wavelength range. The polyimide precursors are imidized at 7.5% or more and 36% or less so that they are less soluble in developing solutions and therefore are not dissolved in the developing solutions at unexposed parts. Thus, the resin compositions of the present invention can be used to form a resin film having a precise pattern by exposure and development.
    Type: Grant
    Filed: October 24, 2003
    Date of Patent: August 9, 2005
    Assignee: Sony Chemicals Corp.
    Inventors: Mamiko Nomura, Masatoshi Hasegawa, Junichi Ishii, Tadashi Akamatsu
  • Patent number: 6924348
    Abstract: A polyimide excelling in heat resistance, chemical resistance, water repellency, dielectric characteristics, electrical characteristics, and optical characteristics and a polyamide acid useful as the raw material therefor are provided. Specifically, a polyamide acid containing a chlorine atom and a fluorine atom and comprising a repeating unit represented by the following formula (1): (wherein X and X? independently denote a divalent organic group; Y and Y? independently denote a chlorine, bromine, or iodine atom; p and p? denote independently denote the number of fluorine atom {F in the formula (1)} bonded to the relevant benzene ring, representing an integer of 0-3; q and q? independently denote an integer of 0-3; and p+q total 3, and p?+q? total 3).
    Type: Grant
    Filed: July 11, 2002
    Date of Patent: August 2, 2005
    Assignees: Nippon Shokubai Co., Ltd., NTT Advanced Technology Corporation
    Inventors: Kozo Tajiri, Masayoshi Kuwabara, Yasunori Okumura, Tohru Matsuura, Noriyoshi Yamada
  • Patent number: 6919418
    Abstract: Methods of reducing the amount of undesirable cyclic oligomer by-products in the production of polyetherimides are disclosed. The resulting polyetherimides have enhanced thermomechanical properties.
    Type: Grant
    Filed: August 25, 2003
    Date of Patent: July 19, 2005
    Inventors: Farid Fouad Khouri, Daniel Joseph Brunelle, Donald Scott Johnson
  • Patent number: 6919422
    Abstract: A polyimide composition and a process to prepare polyimide resins with reduced plate out and mold deposits is described. During resin molding operations the low plate out resins show a longer period of operation between cleaning of equipment leading to more efficient operation.
    Type: Grant
    Filed: September 22, 2003
    Date of Patent: July 19, 2005
    Assignee: General Electric Company
    Inventors: Robert R Gallucci, Roy Ray Odle, William A. Kernick, III, Mark Alan Sanner
  • Patent number: 6916898
    Abstract: A process of preparing a polyimide of the present invention comprises effecting an imidization reaction of a diamine and a tetracarboxylic dianhydride in a solvent containing 50 to 100% by weight of an equimolar composition of a nitrogen-containing cyclic compound indicated by chemical formula (1) below and a phenol indicated by chemical formula (2) below: in formula (1), X represents —CH2— or —N(CH3)—, and in formula (2), R1 and R2 may be the same as, or different from, each other and represent each any one of —H, —OH, —CH3, —C2H5, —C3H7, —C4H9, —C5H11, —C6H13, —C7H15, —C8H17, —C9H19, —C10H21, —OCH3, —O(C6H5), —NO2, —Cl, —Br and —F.
    Type: Grant
    Filed: March 13, 2001
    Date of Patent: July 12, 2005
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Takashi Kuroki, Atsushi Shibuya, Shoji Tamai
  • Patent number: 6911519
    Abstract: A series of low melting and low viscosity phenylethynyl end-capped polyimides (PETIs) possessed of long term thermal and mechanical stability useful as films, melt coatings, adhesives, matrix and RTM resins and particular as coatings for optical fibers and phenylethynyl end-capped bismides blended with PETIs are disclosed. Processes for their production including: 1) modification of PETI-5 oligomer by molecular weight adjustments by blending with reactive low melting phenylethynyl end-capped imide monomers, 2) modification of the PETI-5 backbone structure with other diamine components, and 3) modification of the PETI-5 backbone with bulky fluorinated groups are also disclosed.
    Type: Grant
    Filed: March 25, 2003
    Date of Patent: June 28, 2005
    Assignee: University of Connecticut
    Inventors: Daniel A. Scola, Christopher D. Simone
  • Patent number: 6911296
    Abstract: The present invention also includes an imageable element, comprising a substrate and a thermally imageable composition comprising a thermally sensitive polymer which exhibits an increased solubility in an aqueous developer solution upon heating. The thermally sensitive polymer includes at least one covalently bonded unit and at least one thermally reversible non-covalently bonded unit, which includes a two or more centered H-bond within each of the non-covalently bonded unit. The present invention also includes a method of producing the imaged element. The present invention still further includes a thermally imageable composition comprising comprising a thermally sensitive polymer according to the present invention and a process for preparing the thermally sensitive polymer, which is a supramolecular polymer.
    Type: Grant
    Filed: November 19, 2002
    Date of Patent: June 28, 2005
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Peter S. Pappas, Alan Monk, Shashikant Saraiya, Jianbing Huang
  • Patent number: 6908685
    Abstract: The invention provides a polyimide film manufactured from a polyamic acid prepared from pyromellitic dianhydride in combination with 10 to 60 mol % of phenylenediamine and 40 to 90 mol % of 3,4?-oxydianiline, based on the overall diamine. The polyimide film, when used as a metal interconnect board substrate in flexible circuits, chip scale packages (CSP), ball grid arrays (BGA) or tape-automated bonding (TAB) tape by providing metal interconnects on the surface thereof, achieves a good balance between a high elastic modulus, a low thermal expansion coefficient, alkali etchability and film formability.
    Type: Grant
    Filed: August 23, 2001
    Date of Patent: June 21, 2005
    Assignees: E. I. du Pont de Nemours and Company, DuPont-Toray Co. Ltd.
    Inventors: Kenji Uhara, Kouichi Sawasaki, Naofumi Yasuda, Brian C. Auman, John D. Summers
  • Patent number: 6891067
    Abstract: The present invention provides an optical polyimide precursor for use in making a polyimide. The precursor is defined by the following formula: wherein X is Cl, Br, oxo-halide, or fully halogenated alkyl, and A is a divalent aromatic or halogenated aromatic moiety. The present invention provides a method of preparing a diamine compound for use as an optical polyimide precursor. The method includes the steps of dissolving 2-chloro-5-nitrobenzotrifluoride and a diol in N,N-dimethylacetamide to form a solution, adding potassium carbonate, tert-butylammonium chloride and copper powder to said solution and heating the resulting mixture, removing the copper, precipitating and recrystallizing a dinitro-compound resulting from heating the mixture, and dissolving the dinitro-compound and reducing the dinitro-compound to yield a diamine compound.
    Type: Grant
    Filed: October 8, 2002
    Date of Patent: May 10, 2005
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Kyung-Hee You, Kwan-Soo Han, Tae-Hyung Rhee, Eun-Ji Kim, Jung-Hee Kim, Woo-Hyeuk Jang
  • Patent number: 6887580
    Abstract: An adhesive polyimide resin which comprises a siloxane polyimide resin obtained from (A) an aromatic tetracarboxylic dianhydride and (B) a diamine ingredient comprising (B1) a diamine having a phenolic hydroxyl group, carboxyl group, or vinyl group as a crosslinkable reactive group and (B2) a siloxanediamine and has a glass transition temperature of 50 to 250?C and a Young's modulus (storage modulus) at 250?C of 105 Pa or higher; and a laminate which comprises a substrate comprising a conductor layer and an insulating supporting layer having at least one polyimide resin layer and, disposed on a surface of the substrate, an adhesive layer comprising a layer of the adhesive polyimide resin. The adhesive polyimide resin and the laminate have satisfactory adhesion strength even after exposure to a high temperature of up to 270?C and further have excellent heat resistance in reflow ovens. They are hence suitable for use in the bonding of electronic parts.
    Type: Grant
    Filed: January 26, 2001
    Date of Patent: May 3, 2005
    Assignee: Nippon Steel Chemical Co., Ltd.
    Inventors: Kiwamu Tokuhisa, Akira Tokumitsu, Kazuaki Kaneko
  • Patent number: 6887967
    Abstract: A thermosetting polyimide resin composition is provided which comprises a polyimide resin and an epoxy resin, which has excellent heat resistance, low dielectric constant and low dielectric loss tangent and also yields a cured article having good mechanical properties such as tensile strength and tensile elongation. Also, a process for producing a polyimide resin used in the polyimide resin composition is provided. The thermosetting polyimide resin composition comprises a polyimide resin (X), which has a carboxyl group and a linear hydrocarbon structure having a number-average molecular weight of 300 to 6,000, and an epoxy resin (Y).
    Type: Grant
    Filed: January 23, 2003
    Date of Patent: May 3, 2005
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Eiju Ichinose, Yohzoh Yamashina, Hidenobu Ishikawa
  • Patent number: 6881815
    Abstract: A method for the synthesis of poly(etherimide)s comprises the reaction of 4-halotetrahydrophthalic anhydride with an activating primary amine to yield an activated 4-halotetrahydrophthalimide. Activated 4-halotetrahydrophthalimide may then be aromatized and treated with the disodium salt of a bis(phenol) to yield an activated bisimide. The activated bisimide may then be directly treated with a diamine to yield poly(etherimide)s.
    Type: Grant
    Filed: September 25, 2002
    Date of Patent: April 19, 2005
    Assignee: General Electric Company
    Inventors: Roy Ray Odle, Thomas Link Guggenheim
  • Patent number: 6861497
    Abstract: A polyimide is disclosed of the formula: CG1 and CG2 are independently electron-accepting and/or electron-donating groups; x is an integer from about 3 to about 3000; ODAH is any of a number of known dianhydride residues; ODAM is any of a number of known diamine residues; and m, n, o, and p cumulatively add to 1.0, with the sum of m and n ranging from about 0.05 to about 1.0, the sum of o and p ranging from about 0 to about 0.95, the sum of m and o being about 0.5 and the sum of n and p being about 0.5. In addition, a film structure comprising the polyimide and devices utilizing the film structure are disclosed.
    Type: Grant
    Filed: October 28, 2002
    Date of Patent: March 1, 2005
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Geoffrey A. Lindsay, Richard A. Hollins, Peter Zaras, Andrew J. Guenthner, Andrew P. Chafin, Mathew C. Davis, Stephen Fallis
  • Patent number: 6852826
    Abstract: In a step of polymerizing polyamic acid by mixing tetracarboxylic acid dianhydride and diamine and polycondensating the tetracarboxylic acid dianhydride and diamine under the presence of a polymerization-use solvent, a tetracarboxylic acid dianhydride slurry in which a tetracarboxylic acid dianhydride is dispersed in a dispersion medium is used. According to this, it is possible to directly manufacture a polyamic acid solution having a high concentration of polyamic acid more than or equal to 10% by weight. Especially, even if a tetracarboxylic acid dianhydride having low solubility in the polymerization-use solvent, it is possible to effectively manufacture a polyamic acid solution having high solids content, by a simple process and in a short time.
    Type: Grant
    Filed: December 19, 2002
    Date of Patent: February 8, 2005
    Assignee: Kanera Corporation
    Inventors: Kan Fujihara, Kazuhiro Ono, Kiyokazu Akahori
  • Patent number: 6849706
    Abstract: Copolyetherimides comprise phthalimide structural units comprising both 3- and 4-linkages, wherein the designations 3-linkage and 4-linkage refer to the isomeric positions on the phthalimide ring in the totality of phthalimide-comprising structural units in the copolymer. The products have excellent properties, including high glass transition and heat distortion temperatures, high ductility and good melt flow properties, and low polydispersity.
    Type: Grant
    Filed: August 25, 2003
    Date of Patent: February 1, 2005
    Assignee: General Electric Company
    Inventors: Daniel Joseph Brunelle, Havva Yagci Acar, Farid Fouad Khouri, William David Richards
  • Patent number: 6828408
    Abstract: An aromatic polyimide ester having a small coefficient of linear expansion, small water absorbing property, and excellent heat resistance. The aromatic polyimide ester comprising: a repeating unit represented by a following formula (I), a repeating unit represented by a following formula (II), (n represents 0 or 1) a repeating unit represented by a following formula (III), and a repeating unit represented by a following formula (IV), (-A- represents —O— or —CO—, and is located in para-position or meta position to imido group, and X represents direct coupling, —O—, —S—, or —SO2—) and the repeating units are mutually bonded with each other through ester-bonds.
    Type: Grant
    Filed: September 5, 2002
    Date of Patent: December 7, 2004
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Satoshi Okamoto, Manabu Hirakawa
  • Patent number: 6808818
    Abstract: A fusible polyimide showing a fusion endothermic peak in a differential scanning calorimeter has a recurring unit of the following formula (1): in which Ar1 is a mixture of residues of tetracarboxylic dianhydrides composed of 12-25 mol. & of a residue of pyromellitic dianhydride, 5-15 mol. % of a residue of 3,3′4,4′-benzophenonetetracarboxylic dianhydride, and a remaining mol. % of a residue of 3,3′,4,4′-biphenyltetracarboxylic dianhydride, and Ar2 is an aromatic diamine residue composed of 1,3-bis(4-aminophenoxy)benzene.
    Type: Grant
    Filed: October 11, 2002
    Date of Patent: October 26, 2004
    Assignee: Ube Industries, Ltd.
    Inventors: Hideki Ozawa, Shigeru Yamamoto
  • Patent number: 6790930
    Abstract: The present invention provides a method for easily producing a high-molecular weight polyimide resin at high yield by drying and heating a mixture mixed by material monomers of polyimide.
    Type: Grant
    Filed: April 4, 2002
    Date of Patent: September 14, 2004
    Assignee: Kaneka Corporation
    Inventors: Takeshi Kikuchi, Hiroyuki Tsuji, Koji Okada, Hiroyuki Furutani, Koichiro Tanaka, Shoji Hara, Hitoshi Nojiri
  • Patent number: 6784276
    Abstract: This invention is a highly concentrated stable solution of polyimide precursors (monomers) having a solids content ranging from about 80 to 98 percent by weight in lower aliphatic alcohols i.e. methyl and/or ethyl alcohol. The concentrated polyimide precursor solution comprises effective amounts of at least one aromatic diamine, at least one aromatic dianhydride or a lower molecular weight alkyl ester of said dianhydride, and a monofunctional endcap including monoamines, monoanhydrides and the lower alkyl esters of said monoanhydrides. These concentrated polyimide precursor solutions are particularly useful for the preparation of fibrous prepregs and composites for use in structural materials for military and civil applications.
    Type: Grant
    Filed: July 25, 2002
    Date of Patent: August 31, 2004
    Assignee: The United States of America as represented by the United States National Aeronautics and Space Administration
    Inventor: Chun-Hua Chuang
  • Patent number: 6780960
    Abstract: A method of making a solution of a polyimide from a diamine monomer and a dianhydride monomer is disclosed. A solution or slurry of one of the monomers in a solvent that boils at a temperature between about 80° C. and about 160° C. is prepared. The solution or slurry is heated to a temperature between about 80° C. and about 160° C. and the other monomer is slowly added to the solution or slurry. Polyamic acid that is formed quickly imidizes to form the polyimide.
    Type: Grant
    Filed: July 22, 2002
    Date of Patent: August 24, 2004
    Assignee: Sumitomo Bakelite Company Limited
    Inventors: Michael C. Hausladen, Jin-O Choi
  • Patent number: 6777525
    Abstract: Polyimides having a desired combination of high thermo-oxidative stability, low moisture absorption and excellent chemical and corrosion resistance are prepared by reacting a mixture of compounds including (a) 3,3′,4,4′-benzophenonetetracarboxylic dianhydride (BTDA), (b) 3,4′-oxydianiline (3,4′-ODA), and (c) 5-norbornene-2,3-dicarboxylic anhydride (NA) in a high boiling, aprotic solvent to give 5 to 35% by weight of polyamic acid solution. The ratio of (a), (b), and (c) is selected to afford a family of polyimides having different molecular weights and properties. The mixture first forms a polyamic acid precursor. Upon heating at or above 300° C., the polyamic acids form polyimides, which are particularly suitable for use as a high temperature coating, adhesive, thin film, or composite matrix resin.
    Type: Grant
    Filed: April 1, 2002
    Date of Patent: August 17, 2004
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Ruth H. Pater
  • Patent number: 6770733
    Abstract: A film-formable polyimide copolymer, which comprises two kinds of tetracarboxylic acid dianhydride consisting of (A) pyromellitic acid dianhydride and (B) 3,3′,4,4′-benzophenonetetracarboxylic acid dianhydride, and (C) 6-amino-2-(p-aminophenyl)benzimidazole has a heat-resistant dimensional stability without any deterioration of mechanical properties inherent in the polyimide resin when used as a film.
    Type: Grant
    Filed: January 3, 2003
    Date of Patent: August 3, 2004
    Assignee: Nippon Mektron, Limited
    Inventors: Min Zuo, Jenq-Tain Lin
  • Patent number: 6750317
    Abstract: Polyhydroxyamides are polymerized to form highly-crosslinked, temperature-stable polymers. The polyhydroxyamides include as their central, parent structure a benzenetricarboxylic acid to which side chains containing a terminal reactive group are attached by an amide bond. By way of this reactive group, highly crosslinked polymers can be formed. In addition, the polyhydroxyamide can be added as an additive to polymers in order to bring about three-dimensional crosslinking.
    Type: Grant
    Filed: May 31, 2002
    Date of Patent: June 15, 2004
    Assignee: Infineon Technologies AG
    Inventors: Marcus Halik, Holger Hösch, Sezi Recai, Andreas Walter
  • Patent number: 6743851
    Abstract: A polyimide resin composition comprising a polyimide resin (A) and at least one 1H-tetrazole (B) selected from the group consisting of 1H-tetrazole, 5,5′-bis-1H-tetrazole, and derivatives thereof, and having an excellent rust preventing effect on copper and copper alloys.
    Type: Grant
    Filed: September 25, 2001
    Date of Patent: June 1, 2004
    Assignees: Nippon Zeon Co., Ltd., Fujitsu Limited
    Inventors: Akira Tanaka, Satoshi Tazaki, Yasuhiro Yoneda, Kishio Yokouchi
  • Patent number: 6740728
    Abstract: The present invention relates to methods for the preparation of polyesters, poly(ester amide)s and poly(ester imide)s. The materials obtained by the methods of present invention are useful as fluid separation membranes and as high performance materials.
    Type: Grant
    Filed: May 24, 2002
    Date of Patent: May 25, 2004
    Assignee: Praxair Technology, Inc.
    Inventors: Yong Ding, Benjamin Bikson
  • Patent number: 6740371
    Abstract: An alkyldiamine having excellent polymerization reactivity, a polyimide comprising it as a constituting element, and a liquid crystal alignment film excellent in uniformity of liquid crystal alignment, are presented. Namely, the present invention relates to a diaminobenzene derivative represented by the following general formula (1) and to a polyimide obtained by reacting a diamine containing at least 1 mol % of the diaminobenzene derivative represented by the general formula (1), with at least one compound selected from a tetracarboxylic. dianhydride and its derivatives, to obtain a polyimide. precursor having a reduced viscosity of from 0.05 to 5.0 dl/g (in N-methylpyrrolidone at a temperature of 30° C., concentration: 0.5 g/dl) and ring-closing it, and having a repeating unit represented by the general formula (2). Further, the present invention relates to a liquid crystal alignment film containing at least 1 mol % of the above repeating unit.
    Type: Grant
    Filed: December 26, 2001
    Date of Patent: May 25, 2004
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Kazuyoshi Hosaka, Hideyuki Nawata, Takayasu Nihira, Hideyuki Isogai, Hideyuki Endou, Hiroyoshi Fukuro
  • Patent number: 6737503
    Abstract: The aromatic diamine compound of the present invention is represented by the following formula (1), and from the aromatic diamine compound a polyimide having a repeating unit represented by the following formula (4), which has low-temperature adherability, can be obtained. In the formulas (1) and (4), n is an integer of 3 to 7, each R is independently an atom or a group selected from the group consisting of a hydrogen atom, a halogen atom and a hydrocarbon group, the same or different two hetero atoms selected from nitrogen atoms and oxygen atoms bonded to each benzene ring are at the ortho- or meta-positions to each other on at least one benzene ring, and when n is 3, the hetero atoms are at the ortho- or meta-positions to each other on all the benzene rings. In the formula (4), Y is a tetravalent organic group.
    Type: Grant
    Filed: September 3, 2002
    Date of Patent: May 18, 2004
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Yoichi Kodama, Minehiro Mori, Naoshi Nagai, Masaru Kawaguchi
  • Patent number: 6737502
    Abstract: A solvent-free, catalyst-free and contamination-free method of synthesis of polyimides is disclosed. The method includes polymerizing a diamine with 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA) at a pressure of 0.1-760 mm Hg, preferably a reduced pressure at about 36 mm Hg, and a temperature of 90-400° C., preferably 10-240° C.
    Type: Grant
    Filed: June 6, 2002
    Date of Patent: May 18, 2004
    Assignee: Chung-Shan Institute of Science & Technology
    Inventor: Shean-Jeng Jong
  • Patent number: 6734248
    Abstract: A polyimide resin composition comprising a polyimide resin (A) and at least one 1H-tetrazole (B) selected from the group consisting of 1H-tetrazole, 5,5′-bis-1H-tetrazole, and derivatives thereof, and having an excellent rust preventing effect on copper and copper alloys.
    Type: Grant
    Filed: September 25, 2001
    Date of Patent: May 11, 2004
    Assignees: Nippon Zeon Co., Ltd., Fujitsu Limited
    Inventors: Akira Tanaka, Satoshi Tazaki, Yasuhiro Yoneda, Kishio Yokouchi