Reactant Contains Three Or More Carboxylic Acid Groups Or Is Derivative Thereof Patents (Class 528/188)
  • Patent number: 5708127
    Abstract: The invention relates to a PMR type resin which comprises a mixture of:(a) nadic acid of Formula (Ia) or a derivative thereof ##STR1## (b) a diaminobisimide of Formula (Ib) ##STR2## (c) an aromatic tetracarboxylic acid of Formula (Ic) or a derivative thereof ##STR3## the components (a), (b) and (c) being present in the approximate molar proportions of 2:n:n-1 respectively.
    Type: Grant
    Filed: July 21, 1995
    Date of Patent: January 13, 1998
    Assignee: Commonwealth Scientific and Industrial Research Organisation
    Inventors: Jonathan Howard Hodgkin, Robert Eibl
  • Patent number: 5708128
    Abstract: Novel thermoset polyimide and composite materials comprising the thermoset polyimides and a fibrous reinforcement are prepared according to this invention. The thermoset polyimides are obtained by heat-treating a linear polyamic acid or a linear polyimide prepared by using 4,4'-bis(3-aminophenoxy)biphenyl and pyromellitic dianhydride as essential monomers or by adding 4,4'-diaminodiphenyl ether or 3,3',4,4'-biphenyltetracarboxylic dianhydride to the essential monomers and by end-capping the molecular chain end with an aromatic dicarboxylic anhydride having a carbon-carbon triple bond. The thermoset polyimides have essential excellent properties of thermoplastic polyimide and additionally has enhanced heat resistance and improved mechanical properties. The thermoset polyimide can be used to provide various kinds of composite materials for aircraft matrices, electric and electronic appliances and others.
    Type: Grant
    Filed: June 24, 1996
    Date of Patent: January 13, 1998
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Hideaki Oikawa, Shoji Tamai, Masahiro Ohta, Akihiro Yamaguchi
  • Patent number: 5696235
    Abstract: Novel polyimides which are soluble in various organic solvents and excellent in thermal resistance, processability are disclosed. The polyimides comprise repeating units represented by the following formula (1) and/or (2) and having a number average molecular weight of 4,000-200,000. ##STR1## wherein Ar is a divalent group represented by the following formula (2) or (3): ##STR2## wherein Y is --O--, --CO--, --S--, --SO.sub.2 -- or --C(CH.sub.3).sub.2 --, ##STR3## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each a C.sub.1-4 alkyl group or a C.sub.1-4 alkoxy group, Ra is a divalent group having 2-6 benzene rings, X.sup.1 represents NH, NR (wherein R is a C.sub.1-4 alkyl group or a C.sub.1-4 alkoxy group) or S, Rb is C.sub.2-20 alkylene group, ether group or dimethylsiloxane group, and X.sub.2 represents NH, NR (wherein R is a C.sub.1-4 alkyl group or a C.sub.
    Type: Grant
    Filed: May 17, 1996
    Date of Patent: December 9, 1997
    Assignee: Tomoegawa Paper Co., Ltd.
    Inventors: Osamu Oka, Takeshi Hashimoto, Takeshi Nishigaya
  • Patent number: 5686559
    Abstract: A poly(imide amic ester) having repeating unit of formula (I) and a process for the preparation thereof are provided, wherein formula (I) has the structure ##STR1## wherein Ar is, ##STR2## Ar' is, ##STR3## Ar" is ##STR4## R is selected from the group consisting of CH.sub.3, CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2, CH.sub.2 CH.sub.2 CH.sub.3, CH.sub.2 (CH(CH.sub.3).sub.2 and C(CH.sub.3).sub.3. Further, processes for the preparation of polyimide, polyimide film and polyimide fiber using the above poly(imide amic ester) are provided.
    Type: Grant
    Filed: October 30, 1995
    Date of Patent: November 11, 1997
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Suh Bong Rhee, Myong Hoon Lee, Ji Woong Park
  • Patent number: 5686558
    Abstract: The invention relates to a liquid crystal orientation film having a specific polymer, the main chain of the polymer formed of urea bonds and imide bonds, and a liquid crystal display element incorporating the film. The liquid crystal orientation film does not require high temperature heat treatment when prepared, allowing treatment below about 150.degree. C. Hence, the production of a liquid crystal display element using the liquid crystal orientation film is simplified. Furthermore, other element materials are protected, and the substrate used can be a plastic substrate lower in heat resistance than glass. Moreover, the liquid crystal orientation film is excellent in such properties as liquid crystal orienting capability, heat resistance, transparency, strength and adhesion to the substrate, and has an especially large and stable pre-tilt angle.
    Type: Grant
    Filed: March 29, 1995
    Date of Patent: November 11, 1997
    Assignee: Toray Industries, Inc.
    Inventors: Kazuo Kitamura, Satoshi Okawa
  • Patent number: 5686525
    Abstract: A polyimide precursor composition which is produced by (i) providing a polyamide acid solution obtained by reacting an aromatic tetracarboxylic acid component and a diamine component in the presence of an oxygen-containing solvent and (ii) subjecting said polyamide acid solution to heat treatment. The polyimide precursor composition exhibits a desirable apparent viscosity and a desirable thixotropic property and it excels in film forming ability, and because of this, it enables the formation a high quality relief pattern film with no defect and which excels in form retention by way of the screen printing.
    Type: Grant
    Filed: March 14, 1996
    Date of Patent: November 11, 1997
    Assignee: Central Glass Company, Ltd.
    Inventors: Masamichi Maruta, Hidehisa Nanai, Yoshihiro Moroi, Hiroshi Takahashi, Seiji Hasegawa
  • Patent number: 5670609
    Abstract: A polyimide alignment film based on pyromellitic dianhydride and a 2,2'-bis(perfluoroalkoxy)benzidine, as major components, for use in liquid crystal display devices.
    Type: Grant
    Filed: August 8, 1995
    Date of Patent: September 23, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Brian Carl Auman, Edgar Bohm
  • Patent number: 5668247
    Abstract: The invention provides novel thermoplastic polyimide featuring solid adhesive property under low temperature, low hygroscopic coefficient, and solid resistivity to radioactive rays. The invention also provides novel polyamide acid which is substantially precursor of the thermoplastic polyimide, and also provides novel thermally fusible laminated film for covering conductive wires, featuring solid adhesive property under low temperature, solid resistivity to radioactive rays, and distinct suitability for covering superconductive wires in particular.The novel thermoplastic polyimide is represented by general formula (1) corresponding to the chemical structure shown below; ##STR1## wherein, Ar.sub.1, Ar.sub.2, Ar.sub.4, and Ar.sub.6, respectively designate divalent organic radical, whereas Ar.sub.3 and Ar.sub.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: September 16, 1997
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hiroyuki Furutani, Kazuhisa Danno, Yoshifumi Okamoto, Junya Ida, Yoshihide Oonari, Hitoshi Nojiri, Hirosaku Nagano
  • Patent number: 5665856
    Abstract: A diaminobenzene derivative of the formula (I): ##STR1## wherein each of P and Q which may be the same or different from each other, is a single bond, or a bivalent organic group selected from the group consisting of --O--, --COO-- and --CONH--, R.sub.1 is a C.sub.2-22 straight chain alkylene group, and R.sub.2 is a cyclic group selected from the group consisting of an aromatic ring, an aliphatic ring, a heterocyclic ring and substituted forms of such rings.
    Type: Grant
    Filed: April 25, 1995
    Date of Patent: September 9, 1997
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Takayasu Nihira, Yoshio Miyamoto, Hideyuki Endo, Toyohiko Abe
  • Patent number: 5663287
    Abstract: The present invention provide a novel polyimide which is soluble in organic solvents and excels in heat resistance, and to a process for producing the polyimide. The polyimide of the present invention comprises a repeating unit represented by the formula (1) and having a number average molecular weight of from 4,000 to 200,000. ##STR1## wherein X is --SO.sub.2 -- or --C(.dbd.O)--OCH.sub.2 CH.sub.2 O--C(.dbd.O)--, and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
    Type: Grant
    Filed: March 1, 1996
    Date of Patent: September 2, 1997
    Assignee: Tomoegawa Paper Co., Ltd.
    Inventors: Osamu Oka, Takeshi Hashimoto, Takeshi Nishigaya, Tatsuya Hariko
  • Patent number: 5654396
    Abstract: We achieve solvent resistance and extended use life for advanced polyimides by including at least some solvent-resistant linkages in the backbone in place of phenoxyphenyl sulfone linkages and using diPEPA or PEPA crosslinking end caps.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: August 5, 1997
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 5644022
    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 terminating with an effective amount of a reactive endcapper. The reactive endcappers employed include 4-phenylethynyl phthalic anhydride (PEPA), 3-aminophenoxy-4'-phenylethynylbenzophenone (3-APEB), maleic anhydride (MA) and nadic anhydride (5-norbornene-2,3-dicarboxylic anhydride) (NA). Within a relatively narrow ratio of diamines, from .sup..about. 50% ODA/50% APB to .sup..about. 95% ODA/5% APB, the copolyimides prepared with BPDA and terminated with reactive endgroups have a unique combination of properties that make them very attractive for a number of applications. This unique combination of properties includes low pressure processing (200 psi and below), long term melt stability (several hours at 300.degree. C.
    Type: Grant
    Filed: February 14, 1995
    Date of Patent: July 1, 1997
    Assignee: The United States of America as represented by the Admninistrator of the National Aeronautics and Space Administration
    Inventor: Brian J. Jensen
  • Patent number: 5639850
    Abstract: A process for preparing a tough, soluble, aromatic, thermoplastic copolyimide is provided. The process comprises the steps of (a) providing 4,4'-oxydiphthalic anhydride to 3,4,3',4'-biphenyltetracarboxylic dianhydride at a mole ratio ranging from about 25 mole percent to 75 mole percent to 75 mole percent to about 25 mole percent; (b) adding 3,4'-oxydianiline to form a mixture; c) adding a polar aprotic or polar protic solvent to the mixture to form a solution having a percentage of solids capable of maintaining polymer solubility; (d) stirring the solution to allow it to react; (e) adding an azeotropic solvent to the solution and heating to remove water; (f) cooling the solution of step (e) to room temperature and recovering the tough, soluble, aromatic, thermoplastic copolyimide.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: June 17, 1997
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Robert G. Bryant
  • Patent number: 5637672
    Abstract: Polyamide esters which can be prepared from tetracarboxylic dianhydrides and can be converted into polyimides by alcohol cleavage with cyclization, characterized in that the radicals OR of the ester groups --COOR which are substituted during the polyimide formation are alkoxy radicals having 2 to 5 C atoms which are monosubstituted or polysubstituted by fluorine.Polyimides prepared therefrom are suitable as orientation layers in liquid-crystal display elements and in optical wave guides.
    Type: Grant
    Filed: April 18, 1991
    Date of Patent: June 10, 1997
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Bernhard Rieger, Ekkehard Bartmann, Eike Poetsch
  • Patent number: 5621068
    Abstract: A thermoplastic polyimide film comprising a thermoplastic polyimide polymer, a polyimide laminate, respectively being suited for use as cover-lay adhesive agent and a cover-lay film capable of exerting distinguished thermal resistant property, processability and adhesion property useful for the manufacture of flexible printed circuit boards, and yet, suited for use as the adhesive-agent layers of flexible copper-coated laminates and bilateral adhesive sheets; and a method of manufacturing the polyimide laminate. The thermoplastic polyimide polymer represented by the general formula (1) specified below: ##STR1## wherein Ar.sub.1, Ar.sub.2, Ar.sub.4 and Ar.sub.6, represents divalent organic radical, whereas Ar.sub.3 and Ar.sub.5 represent quadrivalent organic radical, wherein l, m amd n designate positive integer of 0 to 15, wherein the sum of 1 and m is 1 or more than 1, and wherein t designates positive integer of 1 or more than 1.
    Type: Grant
    Filed: February 22, 1995
    Date of Patent: April 15, 1997
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yoshifumi Okamoto, Hiroyuki Furutani, Kazuhisa Danno, Junya Ida, Hirosaku Nagano
  • Patent number: 5621067
    Abstract: Wholly aromatic polyamides and their shaped articles containing at least 85 mole percent of repeat units of m-phenylene isophthalamide: ##STR1## and repeat units of selected aromatic diamines and diacid chlorides exhibit improved flame resistance while retaining good thermal stability.
    Type: Grant
    Filed: March 30, 1995
    Date of Patent: April 15, 1997
    Assignee: Industrial Technology Research Institute
    Inventors: Jin-Chyueh Lin, Jen-Chang Yang, Ting-Hsiu Chen
  • Patent number: 5614607
    Abstract: The invention provides a method of preparing a polyimide by reacting together a dianhydride and a diisocyanate or equivalent, the polyimide having repeating units of the general formula (I): ##STR1## in which D is a group comprising one or more aromatic rings, to which the imide carbon atoms are directly bonded, andE is a group comprising one or more cycloaliphatic or aromatic rings, to which the imide nitrogen atoms are bonded directly or via an aliphatic group, provided that the imide nitrogen atoms are not bonded directly to an aromatic ring. Such polyimide is colourless or of low colour.
    Type: Grant
    Filed: March 30, 1995
    Date of Patent: March 25, 1997
    Assignee: Kabushiki Kaisha Kobe Seiko Sho
    Inventors: John N. Hay, Barry Woodfine
  • Patent number: 5614606
    Abstract: Polyamic acids and corresponding polyimides are prepared by reacting polyfunctional amines, aromatic polyfunctional anhydrides or esters thereof, and allyl-nadic anhydride end capping agents, the resulting products exhibiting excellent properties and being suitable for the preparation of prepregs, composites, adhesives, coatings, and the like.
    Type: Grant
    Filed: December 31, 1986
    Date of Patent: March 25, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Mohammad A. Chaudhari, John J. King, Byung Lee
  • Patent number: 5612450
    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: May 16, 1995
    Date of Patent: March 18, 1997
    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: 5610265
    Abstract: A rigid-rod aromatic polyimide having repeating units of the formula: ##STR1##
    Type: Grant
    Filed: February 2, 1996
    Date of Patent: March 11, 1997
    Assignee: The United States of America as represented by The Secretary of the Air Force
    Inventor: Loon-Seng Tan
  • Patent number: 5608033
    Abstract: A liquid crystal alignment film made of a polyimide which has, on its side chain, a benzene or biphenyl ring substituted by a monovalent substituent having a positive value as the .sigma.p value under Hammett's rule.
    Type: Grant
    Filed: May 5, 1995
    Date of Patent: March 4, 1997
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Takayasu Nihira, Yoshio Miyamoto, Hideyuki Endo, Toyohiko Abe
  • Patent number: 5606014
    Abstract: Controlled molecular weight imide oligomers and co-oligomers containing pendent phenylethynyl groups (PEPIs) and endcapped with nonreactive or phenylethynyl groups have been prepared by the cyclodehydration of the precursor amide acid oligomers or co-oligomers containing pendent phenylethynyl groups and endcapped with nonreactive or phenylethynyl groups. The amine terminated amide acid oligomers or co-oligomers are prepared from the reaction of dianhydride(s) with an excess of diamine(s) and diamine containing pendent phenylethynyl groups and subsequently endcapped with a phenylethynyl phthalic anhydride or monofunctional anhydride. The anhydride terminated amide acid oligomers and co-oligomers are prepared from the reaction of diamine(s) and diamine containing pendent phenylethynyl group(s) with an excess of dianhydride(s) and subsequently endcapped with a phenylethynyl amine or monofunctional amine. The polymerizations are carried out in polar aprotic solvents such as under nitrogen at room temperature.
    Type: Grant
    Filed: August 4, 1995
    Date of Patent: February 25, 1997
    Assignee: The United States of America as represented by the United States National Aeronautics and Space Administration
    Inventors: John W. Connell, Joseph G. Smith, Jr., Paul M. Hergenrother
  • Patent number: 5606013
    Abstract: Polyamic acids and corresponding polyimides are prepared by reacting phenylindane diamines, aromatic polyfunctional anhydrides or esters thereof, and nadic anhydride or allylnadic anhydride end capping agents, the resulting products exhibiting excellent properties and being suitable for the preparation of prepregs, composites, adhesives, coatings, and the like.
    Type: Grant
    Filed: December 31, 1986
    Date of Patent: February 25, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Mohammad A. Chaudhari, John J. King, Byung Lee
  • Patent number: 5599899
    Abstract: A class of rigid rod and latter polymers having light emitting capability is provided. Included in this class of polymers are those having novel repeating structural units. These rigid rod and ladder polymers are employed in light emitting diodes.
    Type: Grant
    Filed: November 1, 1993
    Date of Patent: February 4, 1997
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Samson A. Jenekhe, John A. Osaheni
  • Patent number: 5597889
    Abstract: An alternating copolymer comprising a repeating unit of the formula:--Z--(X-Y).sub.n -- (I)wherein n is at least 2, X is O, S, Se or Te, and Y and Z are independently an aromatic or substituted aromatic group, and at least one other repeating unit, which is useful as a photosensitive material used in a spatial light modulator.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: January 28, 1997
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Akio Takimoto, Hirofumi Wakemoto, Eiichiro Tanaka, Masanori Watanabe, Junko Asayama, Hisahito Ogawa, Shigehiro Sato, Fumiko Yokotani
  • Patent number: 5597890
    Abstract: The present invention is directed to an exciplex formed from a .pi.-conjugated polymer and an electron donor or acceptor component. The present invention also relates to assemblies comprising said exciplex, their use in optoelectrical devices and method of enhancing optoelectrical properties of .pi.-conjugated polymers by forming said exciplex.
    Type: Grant
    Filed: January 26, 1994
    Date of Patent: January 28, 1997
    Assignee: Research Corporation Technologies, Inc.
    Inventor: Samson A. Jenekhe
  • Patent number: 5596073
    Abstract: The present invention relates to solutions which can be directly shaped in anhydrous dimethylalkyleneurea, based on a polyimide obtained from an aromatic dianhydride and an aromatic diisocyanate.It also relates to the process for the production of the above solutions, as well as to a process for spinning these solutions and to the yarns and fibres thus obtained.
    Type: Grant
    Filed: April 14, 1995
    Date of Patent: January 21, 1997
    Assignee: S.N.C. Kermel
    Inventors: Philippe Michaud, Jean Russo
  • Patent number: 5587452
    Abstract: The invention relates to a polyamide-imide containing recurring units according to the formula ##STR1## where Y is an arylene group, andR and R' are alkylene groups, in which at least 50 mole % of R and/or R' is a butylene group.The polyamide-imides are semi-crystalline.They are suitable for injection moulding applications, structural moulded parts, films, coatings and fibres. They can preferably be used in fields of application where temperatures above 200.degree. C. occur.
    Type: Grant
    Filed: July 3, 1995
    Date of Patent: December 24, 1996
    Assignee: DSM N.V.
    Inventors: Cornelis E. Koning, Lilian M. J. Teuwen
  • Patent number: 5578696
    Abstract: A heat-resistant adhesive film, an adhesion structure obtained using the same, and an adhesion method using the same are disclosed, the film comprising a polyisoimide resin containing at least 40 mol % of an isoimide unit represented by formula (I): ##STR1## wherein R.sub.1 represents a tetravalent aromatic or aliphatic residue; R.sub.2 represents a divalent aromatic or aliphatic residue; and the arrow represents a bond replaceable on isomerization, in the molecule thereof. The isoimide unit of the polyisoimide resin is easily converted to an imide unit on heating, e.g., hot pressing with an adherend, to provide a cover-lay film or a single-sided or double-sided base for printed circuit boards having excellent adhesion, heat resistance, dimensional precision, and workability.
    Type: Grant
    Filed: April 6, 1994
    Date of Patent: November 26, 1996
    Assignee: Nitto Denko Corporation
    Inventors: Amane Mochizuki, Kazumi Higashi, Masako Maeda
  • Patent number: 5578697
    Abstract: A polyimide precursor having a molecular structure obtained by polymerizing (a) 0.97 to 1.03 molar equivalent of a diamine component containing 0.40 molar equivalent or more of aromatic diamine compound represented by the general formula (DA1), and (b) an acid anhydride component containing (1-n.sub.1 /2) molar equivalent of a tetracarboxylic dianhydride and n.sub.1 molar equivalent of at least one selected from the group consisting of maleic anhydride and maleic derivative anhydride, wherein n.sub.1 ranges from 0.02 to 0.40.
    Type: Grant
    Filed: March 29, 1995
    Date of Patent: November 26, 1996
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Yoshiaki Kawamonzen, Masayuki Oba, Yukihiro Mikogami, Shigeru Matake, Shuzi Hayase, Satoshi Mikoshiba
  • Patent number: 5569738
    Abstract: This invention relates to melt processable copolymer of etherimideimide/etherimide herein-after identified as PEII/PEI copolymer of following structural formula(I). ##STR1## wherein, R and R' are independently selected from the groups of ##STR2## Ar and Ar' are independently selected from the groups of ##STR3## (wherein, R1 is H or C1-C6 alkyl group,R2 is II or C1-C4 alkyl group, andR3 is --O--, --CO--, --SO--, --SO2--.); andn and m are independently an integer between 5 and 500.
    Type: Grant
    Filed: March 14, 1995
    Date of Patent: October 29, 1996
    Assignees: Korea Research Institute of Chemical Technology, Cheil Industries, Inc.
    Inventors: Kil Y. Choi, Jong C. Won, Young T. Hong, Sang S. Woo, Youn S. Don
  • Patent number: 5567800
    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 28, 1994
    Date of Patent: October 22, 1996
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Paul M. Hergenrother, Joseph G. Smith, Jr.
  • Patent number: 5539080
    Abstract: A process is disclosed for making circuit elements by photolithography comprising depositing an antireflective polyimide or polyimide precursor layer on a substrate and heating the substrate at 200.degree. C. to 500.degree. to provide a functional integrated circuit element that includes an antireflective polyimide layer. The antireflective polyimide layer contains a sufficient concentration of at least one chromophore to give rise to an absorbance sufficient to attenuate actinic radiation at 405 or 436 nm. Preferred chromophores include those arising from perylenes, naphthalenes and anthraquinones. The chromophore may reside in a dye which is a component of the polyimide coating mixture or it may reside in a residue which is incorporated into the polyimide itself.
    Type: Grant
    Filed: April 19, 1995
    Date of Patent: July 23, 1996
    Assignee: International Business Machines Corporation
    Inventors: Dennis P. Hogan, Harold G. Linde, Ronald A. Warren
  • Patent number: 5521276
    Abstract: Polyamideimide resins having the formula (I) ##STR1## in which repeating units are bound in a head to tail or head to head manner,R is at least two divalent groups selected from the group consisting of ##STR2## (cis-, trans- conformational mixture) wherein one divalent group is ##STR3## group in a PAI molecule, produced by introducing isophorone diamine into the conventional aromatic polyamideimide resins.
    Type: Grant
    Filed: June 22, 1994
    Date of Patent: May 28, 1996
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Kil-Yeong Choi, Mi-Hie Yi, Jae-Heung Lee, Moon-Young Jin, Young-Taik Hong
  • Patent number: 5516875
    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: December 15, 1994
    Date of Patent: May 14, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Howard E. Simmons, III
  • Patent number: 5508357
    Abstract: A polyimide comprises structural units represented by the following formula: ##STR1## wherein Ar is a group consisting of 10-90 mole % of a first specific structural sub-unit and 90-10 mole % of a second particular structural sub-unit. A process for the production of the polyimide and a thermosetting resin composition comprising the polyimide and a particular polymaleimide are also disclosed.
    Type: Grant
    Filed: September 16, 1994
    Date of Patent: April 16, 1996
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Hidekazu Matsuura, Yoshihide Iwasaki, Kaori Ikeda, Takayuki Suzuki, Masashi Tanaka, Yasuo Miyadera
  • Patent number: 5508377
    Abstract: This invention relates to a novel polyimide or polyimide copolymer having excellent heat resistance and greatly improved processability, 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.The polyimide comprise a requisite structural unit having one or more recurring structural units of the formula: ##STR1## wherein L is an oxygen atom, carbonyl, isopropylidene or hexafluoroisopropylidene, and X is ##STR2## and Ar is a tetravalent radical having 6 to 27 carbon atoms and being selected from the group consisting of a monoaromatic radical, condensed polyaromatic radical and noncondensed polyaromatic radical having aromatic radicals connected to each other with a direct bond or a bridge member.
    Type: Grant
    Filed: December 13, 1994
    Date of Patent: April 16, 1996
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Wataru Yamashita, Yuichi Okawa, Shoji Tamai, Akihiro Yamaguchi
  • Patent number: 5502157
    Abstract: A copolyimide was prepared by reacting 3,4'-oxydianiline (3,4'-ODA) with a dianhydride blend comprising, based on the total amount of the dianhydride blend, about 67 to 80 mole percent of 4,4'-oxydiphthalic anhydride (ODPA) and about 20 to 33 mole percent of 3,3',4,4'-benzophenonetetracarboxylic dianhydride (BTDA). The copolyimide may be endcapped with up to about 10 mole percent of a monofunctional aromatic anhydride and has unbalanced stoichiometry such that a molar deficit in the dianhydride blend is compensated with twice the molar amount of the monofunctional aromatic anhydride. The copolyimide was used to prepare composites, films and adhesives. The film and adhesive properties were significantly better than those of LaRC.TM.-IA.
    Type: Grant
    Filed: August 31, 1994
    Date of Patent: March 26, 1996
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Alice C. Chang, Terry L. St. Clair
  • Patent number: 5502156
    Abstract: Disclosed is a thermally-stable SnO.sub.2 -surfaced polyimide film wherein the electrical conductivity of the SnO.sub.2 surface is within the range of about 3.0.times.10.sup.-3 to about 1.times.10.sup.-2 ohms.sup.-1,. Also disclosed is a method of preparing this film from a solution containing a polyamic acid and SnCl.sub.4 (DMSO).sub.2.
    Type: Grant
    Filed: July 28, 1994
    Date of Patent: March 26, 1996
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Anne K. St. Clair, Stephen A. Ezzell, Larry T. Taylor, Harold G. Boston
  • Patent number: 5498691
    Abstract: Disclosed are bis-meta-benzotrifluoride compounds having the general formula ##STR1## where each A is independently selected from the group consisting of NO.sub.2, NH.sub.2, and NH.sub.3.sup.+ Z.sup.-, Z.sup.- is an anion and B is selected from the group consisting of O, CO, S, SO, and SO.sub.2. The diamine compounds are useful as monomers in making polyimides, polyamide-imides, and polyamides.
    Type: Grant
    Filed: October 9, 1990
    Date of Patent: March 12, 1996
    Assignee: Occidental Chemical Corporation
    Inventors: Jeffrey S. Stults, Henry C. Lin, Robert A. Buchanan, Robert L. Ostrozynski
  • Patent number: 5494991
    Abstract: Polyimides comprising recurring units of the following general formula (1) ##STR1## wherein Ar.sub.1 represents a tetravalent aromatic group and each Ar.sub.2 represents a divalent aromatic group. Polyimide copolymers and preparations of the polyimides and the polyimide copolymers are also described.
    Type: Grant
    Filed: June 17, 1994
    Date of Patent: February 27, 1996
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Ichiro Kaneko, Atushi Sugitani, Masahiro Yuyama, Kiyoshi Motomi
  • Patent number: 5493003
    Abstract: Solutions of polyimide-forming substances containA) polyamines andB) amides and/or esters of tetracarboxylic acids, the amido or ester groups carrying substituents selected from the group consisting of carboxyl, sulfo and silicon-containing groups,and are used as polyimide coatings.
    Type: Grant
    Filed: October 11, 1994
    Date of Patent: February 20, 1996
    Assignee: BASF Lacke + Farben Aktiengesellschaft
    Inventors: Rainer Blum, Manfred Schwarz, Gerhard Hoffmann
  • Patent number: 5489669
    Abstract: A polyimide represented by the general formula (1): ##STR1## wherein Y represents a hydrocarbon group having 4 to 20 carbon atoms or a sulfur atom; each of R.sub.1 to R.sub.4, R.sub.i and R.sub.j represents a halogen atom, a hydrocarbon group having 1 to 6 carbon atoms or a halogen-containing hydrocarbon group having 1 to 6 carbon atoms; each of a, b, c, d, e and f represents an integer of 0 to 4 satisfying a+b.ltoreq.4, c+d.ltoreq.4 and e+f.ltoreq.4; and X represents a tetravalent organic group having 2 or more carbon atoms.
    Type: Grant
    Filed: June 30, 1994
    Date of Patent: February 6, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mika Shirasaki, Mitsuhiro Shibata, Shuichi Kanagawa
  • Patent number: 5484879
    Abstract: Polyimide polymers of the following recurring structure and the corresponding polyamic acids are disclosed: ##STR1## wherein AR.sub.1 is ##STR2## where X is O, S, SO, SO.sub.2, CO, C(CF.sub.3).sub.2, C(CH.sub.3).sub.2, Si(CH.sub.3).sub.2, or a single bond, wherein AR.sub.2 may be pyromellitic dianhydride, a substituted pyromellitic dianhydride, naphthanoic dianhydride, or ##STR3## where Y is O, S, SO, SO.sub.2, CO, C(CF.sub.3).sub.2, C(CH.sub.3).sub.2, Si(CH.sub.3).sub.2 --O--AR--O--, or a single bond, where AR is an aromatic nucleus.
    Type: Grant
    Filed: December 17, 1990
    Date of Patent: January 16, 1996
    Assignee: Occidental Chemical Corporation
    Inventors: Robert A. Buchanan, Jeffrey S. Stults, Ronald F. Spohn
  • Patent number: 5480964
    Abstract: A negative birefringent film, useful in liquid crystal displays, and a method for controlling the negative birefringence of a polyimide film is disclosed which allows the matching of an application to a targeted amount of birefringence by controlling the degree of in-plane orientation of the polyimide by the selection of functional groups within both the diamine and dianhydride segments of the polyimide which affect the polyimide backbone chain rigidity, linearity, and symmetry. The higher the rigidity, linearity and symmetry of the polyimide backbone, the larger the value of the negative birefringence of the polyimide film.
    Type: Grant
    Filed: April 21, 1994
    Date of Patent: January 2, 1996
    Assignee: The University of Akron
    Inventors: Frank W. Harris, Stephen Z. D. Cheng
  • Patent number: 5480965
    Abstract: This invention relates to a novel thermoplastic and amorphous polyimide which is readily soluble in organic solvent, a novel aromatic diamino compound used for the polyimide, a preparation process thereof, a polyimide-based resin composition comprising the thermoplastic polyimide and a fibrous reinforcement, a process for preparing the resin composition, an injection molded article of the resin composition, a polyimide-based composite obtained by molding the above soluble and thermoplastic polyimide in combination with a fibrous reinforcement, and a fibrous reinforcement having a surface modified with the above polyimide.
    Type: Grant
    Filed: July 26, 1994
    Date of Patent: January 2, 1996
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Wataru Yamashita, Yuichi Okawa, Hideaki Oikawa, Tadashi Asanuma, Yuko Ishihara, Mitsunori Matsuo, Keizaburo Yamaguchi, Akihiro Yamaguchi, Shoji Tamai
  • Patent number: 5478916
    Abstract: A solvent resistant copolyimide was prepared by reacting 4,4'-oxydiphthalic anhydride with a diaimine blend comprising, based on the total amount of the diamine blend, about 75 to 90 mole percent of 3,4'-oxydianiline and about 10 to 25 mole percent p-phenylene diamine. The solvent resistant copolyimide had a higher glass transition temperature when cured at 350.degree. , 371.degree. and 400.degree. C. than LaRC.TM.-IA. The composite prepared from the copolyimide had similar mechanical properties to LaRC.TM.-IA. Films prepared from the copolyimide were resistant to immediate breakage when exposed to solvents such as dimethylacetamide and chloroform. The adhesive properties of the copolyimide were maintained even after testing at 23.degree., 150.degree., 177.degree. and 204.degree. C.
    Type: Grant
    Filed: September 1, 1994
    Date of Patent: December 26, 1995
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Alice C. Chang, Terry L. St. Clair
  • Patent number: 5478914
    Abstract: Polyimides comprising recurring units of the following general formula (1) ##STR1## wherein R.sub.1 represents a tetravalent aromatic group. Polyimide copolymers and preparations of the polyimides and the polyimide copolymers are also described.
    Type: Grant
    Filed: July 1, 1994
    Date of Patent: December 26, 1995
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Ichiro Kaneko, Atushi Sugitani, Masahiro Yuyama, Kiyoshi Motomi
  • Patent number: 5478917
    Abstract: Solutions of polyimide-forming substances containA) aromatic or partly aromatic polyamines andB) amides or a mixture of esters and amides of tetracarboxylic acids.Solutions are useful as coating compositions.
    Type: Grant
    Filed: October 11, 1994
    Date of Patent: December 26, 1995
    Assignee: BASF Lacke + Farben Aktiengesellschaft
    Inventors: Rainer Blum, Gerhard Hoffmann
  • Patent number: 5478913
    Abstract: Copolyimides from 1,4-bis(4-aminophenoxy)-2-phenylbenzene and m- or p-phenylene diamine with biphenyl dianhydride exhibit a high Tg and reduced melt viscosity.
    Type: Grant
    Filed: August 31, 1994
    Date of Patent: December 26, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Richard J. Boyce, Thomas P. Gannett, James M. Sonnett, Murty S. Tanikella, Brian C. Auman