Phenolic Reactant Contains At Least Two Aryl Rings And Two Diverse Phenolic To Oxygen Bonds Patents (Class 528/185)
  • Patent number: 6350817
    Abstract: Phenylethynyl containing reactive additives were prepared from aromatic diamines containing phenylethynyl groups and various ratios of phthalic anhydride and 4-phenylethynylphthalic anhydride in glacial acetic acid to form the imide in one step or in N-methyl-2-pyrrolidinone to form the amide acid intermediate. The reactive additives were mixed in various amounts (10% to 90%) with oligomers containing either terminal or pendent phenylethynyl groups (or both) to reduce the melt viscosity and thereby enhance processability. Upon thermal cure, the additives react and become chemically incorporated into the matrix and effect an increase in crosslink density relative to that of the host resin. This resultant increase in crosslink density has advantageous consequences on the cured resin properties such as higher glass transition temperature and higher modulus as compared to that of the host resin.
    Type: Grant
    Filed: April 13, 1999
    Date of Patent: February 26, 2002
    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: 6346597
    Abstract: A process for preparing a polyester carbonate is provided. The process comprises the steps of: (I) reacting a diacid with a carbonic acid diester and a catalyst in the presence of a polycarbonate oligomer via melt condensation polymerization to form a pre-polymer; and (II) reacting the pre-polymer via solid state polymerization to form a polyester carbonate.
    Type: Grant
    Filed: December 27, 1999
    Date of Patent: February 12, 2002
    Assignee: General Electric Company
    Inventors: Timothy Edward Banach, Gregory Ronald Gillette
  • Patent number: 6335416
    Abstract: A polyimide film, which is produced from polyamide acid prepared through the reaction of p-phenylenebis(trimellitic acid monoester anhydride), oxydiphthalic acid dianhydride, p-phenylenediamine, and 4,4′-diaminodiphenylether in an organic solvent, and which has a high elastic modulus, a high elongation, a low coefficient of linear expansion which is not quite different from that of copper, and a low coefficient of hygroscopic expansion.
    Type: Grant
    Filed: April 25, 2000
    Date of Patent: January 1, 2002
    Assignee: Kaneka Corporation
    Inventors: Hitoshi Nojiri, Koichiro Tanaka
  • Patent number: 6333391
    Abstract: A process for the preparation of an oligomeric polyimide comprises: mixing a tetracarboxylic acid, a dianhydride, a partially hydrolysed dianhydride or a mixture thereof with a diamine in a reaction medium comprising greater than 80% by weight water, and heating mixture in said reaction medium at a temperature above 100° C. for a time sufficient to form said oligomeric polyimide.
    Type: Grant
    Filed: April 21, 2000
    Date of Patent: December 25, 2001
    Assignees: Commonwealth Scientific and Industrial Research Organisation, The Boeing Company
    Inventors: Bronwyn Glenice Laycock, David Geoffrey Hawthorne, Jonathan Howard Hodgkin, Trevor Charles Morton
  • Publication number: 20010051705
    Abstract: The invention relates to a fluorine-containing polybenzoxazole including a structural unit represented by the general formula (1): 1
    Type: Application
    Filed: July 16, 2001
    Publication date: December 13, 2001
    Applicant: Central Glass Company, Limited
    Inventors: Kazuhiko Maeda, Yoshihiro Moroi, Michio Ishida, Kentaro Tsutsumi
  • Patent number: 6316574
    Abstract: The present invention provides a liquid crystal display element having an adequate pre-tilt angle for preventing the reverse domain, as well as excellent electrical properties by preparation of the polyamic acid composition for the liquid crystal display element which comprises a polyamic acid A that excels in electrical properties and a polyamic acid B that has side chains, mixed in the ratio A/B of 50/50 to 95/5 (by weight).
    Type: Grant
    Filed: June 19, 2000
    Date of Patent: November 13, 2001
    Assignee: Chisso Corporation
    Inventors: Satoshi Tanioka, Shizuo Murata, Itsuo Shimizu, Kazumi Ito
  • Patent number: 6307008
    Abstract: A polymide useful as an adhesive for semiconductor assemblies having excellent thermal resistance and adhesive strength at high temperatures.
    Type: Grant
    Filed: February 25, 2000
    Date of Patent: October 23, 2001
    Assignee: Saehan Industries Corporation
    Inventors: Kyung Rok Lee, Soon Sik Kim, Kyeong Ho Chang, Jeong Min Kweon
  • Patent number: 6303743
    Abstract: A polyimide for optical communications, which is expressed by the formula (1), a method of preparing the same, and a method of forming multiple polyimide films using the polyimide, wherein the formula (1) is given by X1, X2, X3, A1, A2, B1, B2, B3, D1, D2, E1, E2, Y1, Y2, Y3, Y4, Y5, Y6, Y7, and Y8, are independently selected from the group consisting of hydrogen atom, halogen atom, alkyl group, halogenated alkyl group, aryl group and halogenated aryl group; Z is a simple chemical bond or selected from the group consisting of —O—, —CO—, —SO3—, —S—, —(T)m—, —(OT)m— and —(OTO)m—, wherein T is alkylene or arylene group substituted by at least one of halogen atom and halogenated alkyl group and m is an integer from 1 to 10; and n is an integer from 1 to 39.
    Type: Grant
    Filed: November 17, 1999
    Date of Patent: October 16, 2001
    Assignee: SamSung Electronics Co., Ltd.
    Inventors: Kyung-hee You, Kwan-soo Han, Tae-hyung Rhee
  • Patent number: 6303742
    Abstract: The present invention provides a novel polyimide composition which includes a cinnamoyl group or a derived cinnamoyl group and has photo-reactivity and heat-reactivity inherent to the cinnamoyl group. Further, a novel diamine and an acid dianhydride according to the present invention are materials mainly used for preparing a novel polyimide composition having the cinnamoyl group or the derived cinnamoyl group in a main chain or a side chain.
    Type: Grant
    Filed: December 1, 1999
    Date of Patent: October 16, 2001
    Assignee: Kanekafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Kohji Okada, Hitoshi Nojiri
  • Patent number: 6291122
    Abstract: A branched polyester resin of the Formula wherein n and m represent randomly repeating segments, and the number of n and m segments in the polymer backbone are each of from about 10 to about 10,000; X is an alkylene group, an olefinic group, or an arylene; Y is an organic dioxy group or radical of I, II, or mixtures thereof; Z is an organic trioxy radical of III, IV, or mixtures thereof; and wherein R and R1 is a hydrogen atom or an alkyl group; G is an alkylene or arylene group, and a is 0 or 1.
    Type: Grant
    Filed: September 14, 2000
    Date of Patent: September 18, 2001
    Assignee: Xerox Corporation
    Inventors: Guerino G. Sacripante, Alan E. J. Toth, Marko D. Saban
  • Patent number: 6281323
    Abstract: Terminal-modified imide oligomers with an inherent viscosity of 0.05-1 obtained by reacting 2,3,3′,4′-biphenyltetracarboxylic dianhydride, an aromatic diamine compound and 4-(2-phenylethynyl)phthalic anhydride, and their cured products. There are provided highly practical terminal-modified imide oligomers and their cured products, which cured products have satisfactory heat resistance and mechanical properties.
    Type: Grant
    Filed: November 19, 1999
    Date of Patent: August 28, 2001
    Assignee: Ube Industries, Ltd.
    Inventors: Rikio Yokota, Masatoshi Hasegawa, Hiroaki Yamaguchi
  • Patent number: 6277950
    Abstract: The present invention provides polyimides and co-polyimides that are organosoluble. The polyimides and co-polyimides are prepared from an aromatic diamine having ortho-linked phenylene and pendant tert-butyl group, i.e., 1,2-bis(4-aminophenoxy)-4-tert-butyl-benzene, or its mixture with other diamines, and a mixture of dianhydrides that containing at least one dianhydride selected from s-BPDA, DSDA, ODPA, 6FDA and other diether-dianhydrides.
    Type: Grant
    Filed: January 26, 2000
    Date of Patent: August 21, 2001
    Assignee: National Science Council
    Inventors: Chin-Ping Yang, Sheng-Huei Hsiao, Shin-Hung Chen
  • Patent number: 6274699
    Abstract: Polyimides and the process for preparing polyimides having improved thermal-oxidative stability derived from the polymerization of effective amounts of one or more of the polyamines such as the aromatic diamines, one or more of the tetracarboxylic dianhydrides and a novel dicarboxylic endcap having a formula selected from the group consisting of: wherein R1 is either a radical where R is either hydrogen or an alkyl radical of 1 to 4 carbons, R2 is either OH, NH2, F, or Cl radical, R3 is either H, OH, NH2, F, Cl or an alkylene radical, R4 is either an alkyl, aryl, alkoxy, aryloxy, nitro, F, or Cl radical, and R5 is either H, alkyl, aryl, alkoxy, aryloxy, nitro, F, or Cl radical. The polyimides are useful particularly in the preparation of prepregs and PMR composites.
    Type: Grant
    Filed: March 23, 2000
    Date of Patent: August 14, 2001
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Mary Ann B. Meador
  • Patent number: 6265521
    Abstract: Polyether polymers such as polyetherimides are prepared by a two-step reaction. The first step is the reaction between an alkali metal salt of a dihydroxy-substituted aromatic hydrocarbon, such as bisphenol A disodium salt, and a substituted aromatic compound such as 1,3-bis[N-(4-chlorophthalimido)]benzene, the alkali metal salt being employed in an amount less than stoichiometric. The intermediate low molecular weight polymer thus produced then undergoes reaction with additional alkali metal salt. By this method, a polyether polymer of closely controlled molecular weight can be conveniently prepared.
    Type: Grant
    Filed: August 7, 2000
    Date of Patent: July 24, 2001
    Assignee: General Electric Company
    Inventors: Thomas Joseph Fyvie, Peter David Phelps, Paul Edward Howson, Donald Frank Rohr, Ganesh Kailasam, Elliott West Shanklin
  • Patent number: 6252033
    Abstract: A method for preparing polyamic acid and polyimide, which is suitable for use in adhesives or adhesive tapes for electronic parts. The polymers have such three-dimensional molecular structures that a significant improvement can be brought about in solvent solubility, thermal resistance, mechanical properties, and adhesive properties onto various substrates. The polyamic acid is prepared by reacting at least one tetracarboxylic dianhydride, at least one aromatic diamine, at least one diamine with a siloxane structure, represented by the following general formula I, and at least one polyamino compound represented by the following general formula II or III. The polyamic acid is converted into polyimide through thermal or chemical imidization.
    Type: Grant
    Filed: March 20, 2000
    Date of Patent: June 26, 2001
    Assignee: Saehan Industries Incorporation
    Inventors: Jeong Min Kweon, Soon Sik Kim, Kyeong Ho Chang, Kyung Rok Lee
  • Patent number: 6235866
    Abstract: Bis(halophthalimides) such as, 3-bis[N-(4-chlorophthalimido)]benzene are prepared in slurry in an organic liquid such as o-dichlorobenzene or anisole, by a reaction at a temperature of at least 150° C. between at least one diamino compound, preferably an aromatic diamine such as m- or p-phenylenediamine, and at least one halophthalic anhydride such as 4-chlorophthalic anhydride, in the presence of an imidization catalyst such as sodium phenylphosphinate. The solids content of the reaction mixture is at least about 5% and preferably at least about 12% by weight. The product slurry may be employed directly in the preparation of polyetherimides, and similar slurries may be employed to prepare other polyether polymers.
    Type: Grant
    Filed: October 6, 1999
    Date of Patent: May 22, 2001
    Assignee: General Electric Company
    Inventors: Farid Fouad Khouri, Ganesh Kailasam, Joseph John Caringi, Peter David Phelps, Paul Edward Howson
  • Patent number: 6232428
    Abstract: Essentially colorless, transparent polyimide coatings and films prepared by combining aromatic dianhydrides with para-substituted aromatic diamines are provided. The polyimide coatings and films are produced by a process whereby the dianhydride and diamine monomer components are reacted at temperatures of greater than 80° C.
    Type: Grant
    Filed: January 14, 2000
    Date of Patent: May 15, 2001
    Assignee: I.S.T. Corporation
    Inventors: Gary L. Deets, Toshiyuki Hattori
  • Patent number: 6222000
    Abstract: Process for producing highly stretchable, amorphous anisotropic melt-forming polymers having recurring units derived from p-hydroxybenzoic acid, 6-hydroxy-2-naphthoic acid, at least one aromatic diacid and at least one aromatic diol and/or hydroxyamine component, at least a portion of which is 4,4′-biphenol, which process comprises incorporating into such polymers recurring units derived from one or more aromatic monomers that provide the polymers with selected meta-linkages wherein each of said recurring units is present in the polymer in specific amounts.
    Type: Grant
    Filed: January 14, 2000
    Date of Patent: April 24, 2001
    Assignee: Ticona LLC
    Inventors: H. Clay Linstid, III, Dominick L. Cangiano, Ronald N. DeMartino, James E. Kuder, Vincent J. Provino
  • Patent number: 6204356
    Abstract: Heat resistant polybenzoxazole resins useful as layer insulation films and protective films for semiconductor, layer insulation films for multilayer circuits, cover coats for flexible copper-clad sheets, solder resist films, liquid crystal-aligned films and the like. These resins have excellent thermal, electrical, physical and mechanical characteristics. Polybenzoxazole precursors are provided, represented by the general formula (A), and are used to obtain polybenzoxazole resins, represented by the general formula (D). In the formulas (A) and (D), n denotes an integer from 2-1000, and X denotes a structure having a formula selected from structures indicated at (B). In the formulas at (B), Y denotes a structure having a formula selected from those indicated at (C), and the hydrogen atom(s) on the benzene ring in these structures are optionally substituted.
    Type: Grant
    Filed: September 27, 1999
    Date of Patent: March 20, 2001
    Assignee: Sumitomo Bakelite Company Limited
    Inventors: Hidenori Saito, Michio Nakajima, Tsuyoshi Watanabe, Maki Tokuhiro
  • Patent number: 6197916
    Abstract: A method for preparing bisphenol A is disclosed, with a selectivity for the p,p′-isomer of greater than about 97%. The method involves reacting phenol with p-isopropenylphenol or 2-(4-hydroxyphenyl)-2-propanol in the presence of a catalyst, at a reaction temperature of no greater than about 65° C. The bisphenol A product is preferably purified by a technique which omits the use of adduct crystallization.
    Type: Grant
    Filed: August 30, 1999
    Date of Patent: March 6, 2001
    Assignee: General Electric Company
    Inventors: Eric James Pressman, Joseph Richard Wetzel
  • Patent number: 6197920
    Abstract: The present invention relates to the synthesis of new type of diamine monomer, 1,3-bis(4-amonophenoxy)naphthalene, and with such a compound to produce a series of aromatic polymers, including polyamide, polyimide, copoly(amide-imide)s, etc., such polymers having excellent resistance to heat and mechanical properties.
    Type: Grant
    Filed: July 21, 1999
    Date of Patent: March 6, 2001
    Assignee: China Textile Institute
    Inventors: Kun Lin Cheng, Wen-Tung Chen
  • Patent number: 6187899
    Abstract: A process for producing polyimide microfine particles which is amenable to free control of particle morphology and particle diameter distribution is provided. A polyamic acid and a polyimide, each in the form of microfine particles with good monodispersibility, are also provided. There is also provided a process for producing polyimide microfine particles from a tetracarboxylic anhydride and a diamine compound which comprises (a) a first step of preparing a first solution containing the tetracarboxylic anhydride and a second solution containing the diamine compound, (b) a second step of mixing the first and second solutions and causing a polyamic acid to precipitate in the form of microfine particles from the mixed solution under ultrasonic agitation, and (c) a third step of imidating the polyamic acid particles to provide the objective polyimide in the form of microfine particles.
    Type: Grant
    Filed: February 25, 1999
    Date of Patent: February 13, 2001
    Assignees: Osaka Prefectural Government, Sumitomo Bekelite Co., Ltd.
    Inventors: Katsuya Asao, Hidenori Saito
  • Patent number: 6184333
    Abstract: The present invention is directed to polyimide systems which simultaneously offer low toxicity, a high glass transition temperature, excellent thermal oxidative stability, and desirable processing characteristics. These various polyimide systems include mixtures of monomeric reactants, polyimide-precursor reaction products, polyimides, and polyimide-containing articles. In one aspect of the invention, the mixture of monomeric reactants includes at least one dia-nhydride or a derivative thereof, and at least one diamine. The diamine may be 4,4′-[1,4-phenylene-bis(1-methylethylidene)]bisaniline, 4,4′-[1,3-phenylene-bis(1-methylethylidene)]bisaniline, and/or a derivative thereof. The diamine also may include a phenylenediamine, 2,2-bis[4-(4-aminophenoxyl)phenyl]propane, 4,4′(1,4-phenylene-bismethylene)bisaniline, and/or a derivative thereof. In addition, the mixture may include a reactive end-capping agent and/or a non-reactive end-capping agent.
    Type: Grant
    Filed: January 15, 1999
    Date of Patent: February 6, 2001
    Assignee: Maverick Corporation
    Inventor: Robert A. Gray
  • Patent number: 6184337
    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. wherein X is —SO2— or —C(═O)—OCH2CH2O—C(═O)—, and R1, R2, R3 and R4 are independently an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
    Type: Grant
    Filed: October 26, 1998
    Date of Patent: February 6, 2001
    Assignee: Tomoegawa Paper Co., Ltd.
    Inventors: Osamu Oka, Takeshi Nishigaya, Fumiyoshi Yamanashi
  • Patent number: 6180747
    Abstract: A branched polyester resin of the Formula wherein n and m represent randomly repeating segments, and the number of n and m segments in the polymer backbone are each of from about 10 to about 10,000; X is an alkylene group, an olefinic group, or an arylene; Y is an organic dioxy group or radical of I, II, or mixtures thereof; Z is an organic trioxy radical of III, IV, or mixtures thereof; and wherein R and R1 is a hydrogen atom or an alkyl group; G is an alkylene or arylene group, and a is 0 or 1.
    Type: Grant
    Filed: February 28, 2000
    Date of Patent: January 30, 2001
    Assignee: Xerox Corporation
    Inventors: Guerino G. Sacripante, Alan E. J. Toth, Marko D. Saban
  • Patent number: 6166174
    Abstract: Polyimide copolymers were obtained containing 1,3-bis(3-aminophenoxy)benzene (APB) and other diamines and dianhydrides and terminating with the appropriate amount of a non-reactive endcapper, such as phthalic anhydride. Homopolymers containing only other diamines and dianhydrides which are not processable under conditions described previously can be made processable by incorporating various amounts of APB, depending on the chemical structures of the diamines and dianhydrides used. Polyimides that are more rigid in nature require more APB to impart processability than polyimides that are less rigid in nature. The copolymers that result from using APB to enhance processability have a unique combination of properties including: excellent thin film properties, low pressure processing (200 psi and below), improved toughness, improved solvent resistance, improved adhesive properties, improved composite mechanical properties, long term melt stability (several hours at 390 C.), and lower melt viscosities.
    Type: Grant
    Filed: August 5, 1999
    Date of Patent: December 26, 2000
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Brian J. Jensen
  • Patent number: 6137008
    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 methyl (--CH.sub.3) and n is an integer ranging from 1 to 4.
    Type: Grant
    Filed: June 2, 1999
    Date of Patent: October 24, 2000
    Assignee: National Science Council
    Inventors: Der-Jang Liaw, Been-Yang Liaw
  • Patent number: 6136949
    Abstract: A compound of the formula: ##STR1## wherein Ar.sup.
    Type: Grant
    Filed: September 3, 1998
    Date of Patent: October 24, 2000
    Assignee: The Dow Chemical Company
    Inventors: Jimmy Dan Earls, Bruce L. Burton, Brenda Thies Colegrove
  • Patent number: 6133401
    Abstract: Polyimide copolymers were obtained containing 1,3-bis(3-aminophenoxy)benzene (APB) and other diamines and dianhydrides and terminating with the appropriate amount of reactive endcapper. The reactive endcappers studied include but should not be limited to 4-phenylethynyl phthalic anhydride (PEPA), 3-aminophenoxy-4'-phenylethynylbenzophenone (3-APEB), maleic anhydride (MA) and nadic anhydride (5-norbornene-2,3-dicarboxylic anhydride, NA). Homopolymers containing only other diamines and dianhydrides which are not processable under conditions described previously can be made processable by incorporating various amounts of APB, depending on the chemical structures of the diamines and dianhydrides used. By simply changing the ratio of APB to the other diamine in the polyimide backbone, a material with a unique combination of solubility, Tg, Tm, melt viscosity, toughness and elevated temperature mechanical properties can be prepared.
    Type: Grant
    Filed: June 29, 1999
    Date of Patent: October 17, 2000
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Brian J. Jensen
  • Patent number: 6132884
    Abstract: Process for producing highly stretchable, amorphous anisotropic melt-forming polymers having recurring units derived from p-hydroxybenzoic acid, 6-hydroxy-2-naphthoic acid, at least one aromatic diacid and an aromatic diol and/or hydroxyamine component, at least a portion of which is 4,4'-biphenol, which comprises incorporating into such polymers recurring units derived from resorcinol and at least one additional monomer that provides the resulting polymer with selected meta linkages, wherein each of said recurring units is present in the polymer in specified amounts.
    Type: Grant
    Filed: January 14, 2000
    Date of Patent: October 17, 2000
    Assignee: Ticona LLC
    Inventors: H. Clay Linstid, III, Dominick L. Cangiano, Ronald N. DeMartino, James E. Kuder, Vincent J. Provino
  • Patent number: 6133407
    Abstract: A polyimide precursor solution having a high concentration yet low viscosity, a polyimide coating film having satisfactory physical properties which is prepared from the polyimide precursor solution, and a process for producing a polyimide coating film using the polyimide precursor solution. The polyimide precursor solution has dissolved therein a specific salt of a diamine and a tetracarboxylic acid and/or a dicarboxylic acid-dialkyl ester in a high concentration, the diamine and the tetracarboxylic acid and/or the dicarboxylic acid-dialkyl ester being capable of forming a polyimide. Also disclosed is a polyimide coating film obtained by heating the solution to cause imidization and a process for producing the polyimide coating film.
    Type: Grant
    Filed: June 23, 1998
    Date of Patent: October 17, 2000
    Assignee: Unitka Ltd.
    Inventors: Hisayasu Kaneshiro, Jushiro Eguchi, Yoshiaki Echigo, Takahiro Ono
  • Patent number: 6133408
    Abstract: A polyimide resin having good thermal stability and good adhesion to a metal foil is disclosed. The polyimide resin is prepared by dissolving at least one diamine in a polar aprotic solvent followed by the addition of an aromatic tetracarboxylic acid dianhydride to the solution of the aromatic diamines to prepare a polyamic acid solution, imidizing this solution to a polyimide resin by heating at a temperature above 250.degree. C., the polar aprotic solvent comprising at least 1 weight % of acetone. Polyimide laminates with a metal foil, such as a copper foil, are also described. The laminates may be used to form flexible printed circuit boards.
    Type: Grant
    Filed: January 15, 1999
    Date of Patent: October 17, 2000
    Assignee: Wirex Corporation
    Inventors: Chien-Hwa Chiu, Der-Jen Sun, Yen-Huey Hsu, Fu-Ti Shiang, Chien-Hsiang Chen, Paul S. C. Wu
  • Patent number: 6127509
    Abstract: Polyimide polymers from 3,4,3',4'-biphenyltetracarboxylic dianhydride and 3,4,3',4'-benzophenonetetracarboxylic dianhydride and a diamine such as p-phenylenediamine exhibit a high glass transition temperature, high thermal oxidative stability and low moisture regain, useful for structural applications.
    Type: Grant
    Filed: June 1, 1999
    Date of Patent: October 3, 2000
    Assignees: E. I. du Pont de Nemours and Company, Fiberite Inc.
    Inventors: James F. Pratte, Murty S. Tanikella
  • Patent number: 6114494
    Abstract: A fully imidized cresylic acid soluble polymer comprising 4,4'- oxydiphthalic anhydride (ODPA), 3,4,3',4',-biphenyltetracarboxylic dianhydride (BPDA), 3,4'-oxydianiline (ODA), and 4,4'-oxydianiline (DAPE) that can be used as a coating material such as a wire coated enamel. The polyimide has relatively low viscosity and high percent solids by substituting some of the 3,4'oxydianiline with 4,4'oxydianiline. Substitution with the 4,4'oxydianiline can be accomplished up to 25% on the molar basis without losing the fully imidized, cresol solubility characteristics.
    Type: Grant
    Filed: December 3, 1998
    Date of Patent: September 5, 2000
    Assignee: Ranbar Electrical Materials, Inc.
    Inventors: Edward W. Kifer, James R. Kwiecinski
  • Patent number: 6111059
    Abstract: A diaminobenzene derivative represented by formula (1), and a polyimide obtained by reacting a diamine containing at least 1 mol % of said diaminobenzene derivative, with a tetracarboxylic acid and its derivatives to obtain a polyimide precursor and ring-closing it, having a repeating unit represented by formula (2), and a liquid crystal alignment film containing said polyimide. ##STR1## P is a single bond or --O--, --COO--, or --CONH--, Q is a cyclic substituent selected from an aromatic ring, an aliphatic ring, a hetero ring and their substitution products, R.sup.1 is an aliphatic ring, and R.sup.2 is C.sub.1-22 straight chain alkyl group, A is a tetravalent organic group constituting a tetracarboxylic acid, B is a bivalent organic group constituting a diamine.
    Type: Grant
    Filed: August 12, 1998
    Date of Patent: August 29, 2000
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Takayasu Nihira, Hideyuki Nawata, Hiroyoshi Fukuro
  • Patent number: 6103322
    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 C.sub.3 -C.sub.20 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 23, 1998
    Date of Patent: August 15, 2000
    Assignee: Elsicon Inc.
    Inventors: Wayne M. Gibbons, Paul Joseph Shannon, Hanxing Zheng
  • Patent number: 6100365
    Abstract: The present invention provides a novel soluble polyimide resin which is superior in solubility in solvents and transparency, which is useful particularly in electronics and optronics fields, and which has good processability; a process for production of the resin; and a solution composition of the resin. A soluble polyimide resin containing, as part or the whole of the diamine units, a 2,5(or 6)-bis(aminomethyl)bicyclo[2.2.1]heptane and having a light transmittance of 60% or more in a range of wavelength larger than 400 nm in an ultraviolet-visible light spectrum measured for a film of 10-.mu.m thickness; a process for production of the resin; and a solution composition of the resin.
    Type: Grant
    Filed: April 12, 1999
    Date of Patent: August 8, 2000
    Inventors: Toshihiko Matsumoto, Toshikazu Kurosaki, Shin Irie, Masaaki Kudo, Yoshiharu Ito, Masao Kaneko
  • Patent number: 6096850
    Abstract: Polyimide is produced by reacting two kinds of diamine compounds consisting of diaminopolysiloxane and a hydroxyl group-containing diamine or three kinds of diamine compounds consisting of diaminopolysiloxane, a hydroxyl group-containing diamine and an aromatic or alicyclic diamine with a 4,4'-(hexafluoroisopropylidene)diphthalic acid dianhydride, thereby once forming a polyamic acid, and subjecting the polyamic acid to polyimidization reaction. The resulting polyimide itself is soluble in low boiling organic solvents for general purpose use, typically methyl ethyl ketone. A photosensitive composition comprising the polyimide, a photo crosslinking agent and a photo acid-generating agent forms a negative type polyimide pattern upon development with an aqueous alkali solution.
    Type: Grant
    Filed: February 26, 1999
    Date of Patent: August 1, 2000
    Assignee: Nippon Mektron Limited
    Inventors: Lin-chiu Chiang, Jenq-Tain Lin, Nobuyuki Sensui
  • Patent number: 6093790
    Abstract: The present invention provides polyimides and co-polyimides that are organosoluble. The polyimides and co-polyimides are prepared from an aromatic diamine having tert-butyl group, i.e., 1,4-bis(4-aminophenoxy)-2-tert-butyl-benzene, or its mixture with other diamines, and a mixture of dianhydrides that containing DSDA or 6FDA or other diether-dianhydrides.
    Type: Grant
    Filed: August 18, 1998
    Date of Patent: July 25, 2000
    Assignee: National Science Council
    Inventors: Chin-Ping Yang, Huei-Wen Yang
  • Patent number: 6084058
    Abstract: A composition for a polyimide type liquid crystal aligning film characterized in that a diamino compound constituting polyimide contains one, two or more diamine selected from 4,4'-diaminodiphenyl methane, 3,3'-dimethyl-4,4'-diaminodiphenyl methane, 2,2'-dimethyl-4,4'-diaminodiphenyl methane, 3,3',5,5'-tetramethyl-4,4'-diaminodiphenyl methane and 4,4'-ethylene di-meta-toluidine.
    Type: Grant
    Filed: September 11, 1998
    Date of Patent: July 4, 2000
    Assignee: Chisso Corporation
    Inventors: Shizuo Murata, Toshiya Sawai, Satoshi Tanioka, Haruo Kato
  • Patent number: 6084053
    Abstract: Electronic parts and a process for manufacturing the electronic parts are provided. The electronic parts comprise an electric insulating material exhibiting a high heat resistance and low dielectric constant as a structural component. The electric insulating material is formed of a polyimide containing a recurring unit represented by the following general formula (1).
    Type: Grant
    Filed: April 15, 1998
    Date of Patent: July 4, 2000
    Assignee: JSR Corporation
    Inventors: Minoru Matsubara, Yasutake Inoue, Mayumi Kakuta, Igor Rozhanskii, Kohei Goto
  • Patent number: 6080832
    Abstract: A diamine-containing polyamic acid alignment layer material provided by the polymerization of aromatic diamine and dianhydride, and having an excellent coating, adhesion and stability. After the polyamic acid alignment layer material is coated and cured at a high temperature, a polyamic acid alignment layer having a pretilt angle of below 2 degrees is formed due to a close ring reaction. The polyamic acid alignment layer with a low pretilt angle can be used in a TN (twisted nematic) type liquid crystal display.
    Type: Grant
    Filed: September 10, 1998
    Date of Patent: June 27, 2000
    Assignee: Industrial Technology Research Institute
    Inventors: Fu-Lung Chen, Ted Hong Shinn, Wen Hishin Wang, Chein-Dhau Lee
  • Patent number: 6077924
    Abstract: Polyimide is produced by reacting two kinds of diamine compounds consisting of diaminopolysiloxane and a hydroxyl group-containing diamine or three kinds of diamine compounds consisting of diaminopolysiloxane, a hydroxyl group-containing diamine and an aromatic or alicyclic diamine with a dicarboxylic acid anhydride having a 2,5-dioxotetrahydrofuryl group as one acid anhydride group, thereby once forming a polyamic acid, and subjecting the polyamic acid to polyimidization reaction. The resulting polyimide itself is soluble in low boiling organic solvents for general purpose use, typically methyl ethyl ketone. A photosensitive composition comprising the polyimide, a photo crosslinking agent and a photo acid-generating agent forms a negative type polyimide pattern upon development with an aqueous alkali solution.
    Type: Grant
    Filed: February 26, 1999
    Date of Patent: June 20, 2000
    Assignee: Nipopon Mektron Limited
    Inventors: Lin-chiu Chiang, Jenq-Tain Lin, Nobuyuki Sensui
  • Patent number: 6072010
    Abstract: A thermoplastic resin composition containing a polyetherimide resin, a siloxane-polyetherimide copolymer and a branched polycarbonate resin exhibits exhibit high heat distortion temperature, improved room temperature impact properties and improved impact strength and ductility at low temperatures.
    Type: Grant
    Filed: December 23, 1997
    Date of Patent: June 6, 2000
    Assignee: General Electric Co.
    Inventor: Robert Puyenbroek
  • Patent number: 6069278
    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 relatively high glass transition temperature and improved mechanical properties at useful temperature ranges.
    Type: Grant
    Filed: November 23, 1999
    Date of Patent: May 30, 2000
    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: 6066710
    Abstract: Disclosed is a method of making an imide-containing polymer by bulk or melt polymerizing monomers. A mixture is formed of (1) a cyclic compound that contains an anhydride group and a second group which is an anhydride, a carboxylic acid, or an ester and (2) a diamine in an amount stoichiometric .+-.5 mole % of stoichiometric with the amount of cyclic compound. An end capper may also be included in the mixture to control the molecular weight but no solvent is used. A polyimidesiloxane can be made by using a siloxane-containing diamine. The mixture is heated to a temperature above the T.sub.g or T.sub.m of the polymer but below its degradation temperature.
    Type: Grant
    Filed: October 29, 1998
    Date of Patent: May 23, 2000
    Assignee: Occidental Chemical Corporation
    Inventors: Kevin H. Becker, Jerold C. Rosenfeld
  • Patent number: 6060575
    Abstract: The present invention provides a series of easily processable poly(ether-imide)s that are organic-soluble and can afford colorless films, their organic solutions and their manufacturing process. The poly(ether-imide) is prepared from a dianhydride and a diamine, wherein the dianhydride is a bis(ether anhydride) having tert-butyl group, i. e. 1,4-bis(3,4-dicarboxyphenoxy)-2-tert-butylbenzene dianhydride.
    Type: Grant
    Filed: April 27, 1999
    Date of Patent: May 9, 2000
    Assignee: National Science Council
    Inventors: Chin-Ping Yang, Sheng-Huei Hsiao
  • Patent number: 6057417
    Abstract: A polymer system having repeating units of the formula: ##STR1## wherein A is --H or --OH, x has a value of 0.5 to 1.0 and y has a value of 1.0-x, exhibits a high glass transition temperature (T.sub.g) and a low dielectric constant. The polymer system is useful in the area of microelectronic packaging.
    Type: Grant
    Filed: May 27, 1999
    Date of Patent: May 2, 2000
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Fred E. Arnold, Thuy D. Dang, Robert J. Spry, Max D. Alexander, Patrick T. Mather
  • Patent number: 6054554
    Abstract: The invention herein relates to a novel soluble polyimide resin comprising polyalicyclic structures and the process of preparation of the same, wherein aromatic tetracarboxylic dianhydride and novel aromatic diamine having an polyalicyclic group with various structures are used to yield a novel form of a polyimide resin, which has superior heat-resistance, solubility, and transparency.More specifically, the invention herein relates to a novel polyimide resin having excellent heat-resistance and solubility, which is prepared by means of reacting diamine monomers having a novel chemical structure with various types of aromatic carboxilic dianhydrides, in stead of aromatic diamine used for the preparation of the conventional polyimide resin. As a result, the polymers so obtained had the glass transition temperature of 260.degree. C..about.410.degree. C. and showed a increase in solubility in proportion to the increase in a number of the aromatic rings between two phenyl groups.
    Type: Grant
    Filed: May 7, 1999
    Date of Patent: April 25, 2000
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Kil Yeong Choi, Mi Hie Yi, Wenxi Huang
  • Patent number: 6046303
    Abstract: The invention herein relates to a soluble polyimide resin for a liquid crystal alignment layer and the manufacturing method thereof, wherein a mixture of aliphatic tetracarboxylic acid dianhydrides and aromatic diamine having aliphatic side chains are used to yield a soluble polyimide resin which has superior heat-resistance, solubility, surface hardness, transparency and liquid crystal alignment capacity.The soluble polyimide resin having alkoxy substituents, for a liquid crystal layer, according to the present invention, is manufactured by adding a mixture of dioxotetrahydrofuran 3-methylcyclohexene-1,2-dicarboxylic dianhydride, which is an aliphatic tetracarboxylic acid dianhydride and aromatic tetracarboxylic acid dianhydride to a mixture of aromatic diamine, and said dioxotetrahydrofuran 3-methylcyclohexene- 1,2-dicarboxylic dianhydride is used in the amount of 50 to 99 mol % to the total amount of anhydrides.
    Type: Grant
    Filed: September 11, 1998
    Date of Patent: April 4, 2000
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Kil-Yeong Choi, Mi-Hie Yi, Moon-Young Jin, Jin-Tae Jung, Jeong-Ghi Koo, Jae-Eun Cho