Carboxylic Acid Or Derivative Is A Reactant Patents (Class 528/173)
  • Patent number: 6350845
    Abstract: Novel polyimides substituted by a substituent having an alkyl or fluoroalkyl group and having reduced water absorption; a process for producing these novel polyimides; and novel acid dianhydrides to be used in the production thereof. A polyimide containing a structure represented by the following general formula (I): wherein X1 represents a tetravalent organic group having a substituent —R1AR2 (wherein A represents a divalent linkage group; R1 represents a single bond or a C1-3 alkylene group; and R2 represents a C1-25 alkyl group or a fluoroalkyl group); and Y represents a divalent organic group.
    Type: Grant
    Filed: June 26, 2000
    Date of Patent: February 26, 2002
    Assignee: Kaneka Corporation
    Inventors: Koji Okada, Shoji Hara, Hitoshi Nojiri
  • Publication number: 20020012862
    Abstract: In a photoconductive element comprising a conductive support, e.g., an electrically conductive film, drum or belt on which a negatively chargeable photoconductive layer is formed, an electrical barrier layer is formed between the support and the photoconductive layer. The barrier layer provides a high energy barrier to the injection of positive charges but transports electrons under an applied electric field. The barrier layer of the invention transports charge by electronic rather than ionic mechanisms and, therefore, is not substantially affected by humidity changes.
    Type: Application
    Filed: June 8, 2001
    Publication date: January 31, 2002
    Applicant: NexPress Solutions, LLC
    Inventors: Louis J. Sorriero, Marie B. O'Regan, Michel F. Molaire
  • Patent number: 6335417
    Abstract: A novel modified polyimide resin having a polybutadiene sheleton and obtainable by reacting the following three (3) kinds of compounds, i.e., a bifunctional hydroxyl-terminal polybutadiene having a number average molecular weight of 800 to 5,000, a tetrabasic acid dianhydride, and a diisocyanate compound, imparts reduced shrinkage upon setting to a thermosetting resin composition comprising the same and also imparts heat resistance and pliability and the like to a hardened mass or article of such thermosetting resin composition. Therefore, such thermosetting resin composition is an excellent resin composition capable of fully satisfying the requirements with regard to the characteristics of an overcoat agent for a wiring circuit which should be pliable, such as a flexible wiring circuit substrate, a film carrier and the like.
    Type: Grant
    Filed: August 17, 2000
    Date of Patent: January 1, 2002
    Assignee: Ajinomoto Co., Inc.
    Inventors: Hiroshi Orikabe, Tadahiko Yokota
  • Patent number: 6335418
    Abstract: A primary object of the invention is to provide a production technology for functional polyamic acid microfine particles and functional polyimide microfine particles by which the particle shape, size and size distribution can be freely controlled. The invention is concerned with a process for synthesizing polyamic acid particles having functional groups at least on the surface from a tetracarboxylic anhydride and a diamine compound characterized by its comprising (a) a first step which comprises providing a tetracarboxylic anhydride and a diamine compound at least one of which has functional groups and preparing a first solution containing the tetracarboxylic anhydride and a second solution containing the diamine compound and (b) a second step which comprises mixing the first and second solutions under ultrasonic agitation to thereby precipitate polyamic acid microfine particles from the mixed solution.
    Type: Grant
    Filed: August 18, 2000
    Date of Patent: January 1, 2002
    Assignees: Osaka Prefectural Government, Sumitomo Bakelite Co., Ltd.
    Inventors: Katsuya Asao, Hitoshi Morita, Hitoshi Onishi, Masaki Kimoto, Yayoi Yoshioka, Hidenori Saito
  • 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: 6333392
    Abstract: An object of the invention is to provide thermosetting amic acid microfine particles, thermosetting imide microfine particles and crosslinked imide microfine particles of controlled particle shape and size distribution. The invention provides a production technology which comprises mixing a first solution containing a tetracarboxylic anhydride and a C═C bond-containing acid anhydride with a second solution containing a diamine compound, causing precipitation of thermosetting amic acid microfine particles from the resulting mixture, and further producing thermosetting imide microfine particles and crosslinked imide microfine particles from the thermosetting amic acid microfine particles.
    Type: Grant
    Filed: May 5, 2000
    Date of Patent: December 25, 2001
    Assignees: Sumitomo Bakelite and Co. Ltd., Osaka Prefectual Government
    Inventors: Katsuya Asao, Hidenori Saito
  • 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
  • Patent number: 6320019
    Abstract: A method for preparing polyamic acid and polyimide of three-dimensional molecular structure such that these polymers are superior in adhesive strength and high-temperature stability while maintaining their inherent thermal resistance and mechanical properties, and thus can be effectively used as an adhesive material for high temperature adhesive tapes suitable for semiconductor assembly.
    Type: Grant
    Filed: February 25, 2000
    Date of Patent: November 20, 2001
    Assignee: Saehan Industries Incorporation
    Inventors: Kyung Rok Lee, Soon Sik Kim, Kyeong Ho Chang, Jeong Min Kweon
  • Patent number: 6316589
    Abstract: A polyimide for optical communications, which is expressed by the formula (1) where R1 and R2 are independently selected from the group consisting of CF3, CCl3, unsubstituted aromatic ring group and halogenerated aromatic ring group; R3 and R4 are independently selected from the group consisting of Cl, F, I, Br, CF3, CCl3, unsubstituted aromatic ring group and halogenated aromatic ring group; and n is an integer from 1 to 39. The polyimides have a superior heat resistance, and can avoid the increase in optical absorption loss due to a refractive index increase and deterioration of adhesive and coating properties due to weak surface tension of a polyimide film. In addition, use of the polyimides as a material for a core layer of optical waveguides can expand the selection range of material for the cladding layer of the optical waveguide.
    Type: Grant
    Filed: April 11, 2000
    Date of Patent: November 13, 2001
    Assignee: SamSung Electronics Co., Ltd
    Inventors: Kyung-Hee You, Kwan-Soo Han, Tae-Hyung Rhee
  • 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: 6307002
    Abstract: A polyimide represented by the following general formula (1); wherein l, m, and n represent not the order of each repeating unit, but the numbers of each repeating unit existing in the molecule, E1 is a photosensitive group, E2 is a group comprising an alkyl group having 2 to 20 carbon atoms, —A(—E1)—, —A(—E2)—, and B each are a divalent organic group, X and Y each are a tetravalent organic group, X, Y, A, B, E1 and E2 may be identical or different among the repeating units, 1 is an integer of 1 or more, m and n each are an integer of 0 or more. The polyimide and polyimide compositions comprising it has thermoreactivity as well as photoreactivity and photosensitivity.
    Type: Grant
    Filed: November 9, 1999
    Date of Patent: October 23, 2001
    Assignee: Kaneka Corporation
    Inventors: Kohji Okada, Hitoshi Nojiri
  • 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: 6307009
    Abstract: An aqueous binder composition suitable for use as a binder in making wool and board products including fiberglass insulation comprising a phenolic resole resin binder made from phenol and formaldehyde by using an excess amount of a basic catalyst.
    Type: Grant
    Filed: December 29, 1999
    Date of Patent: October 23, 2001
    Assignee: Owens Corning Fiberglas Technology, Inc.
    Inventor: Jianjun Li
  • 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: 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: 6303744
    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: October 16, 2001
    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
  • Publication number: 20010029291
    Abstract: An aqueous binder composition suitable for use as a binder in making wool and board products including fiberglass insulation comprising a phenolic resole resin binder made from phenol and formaldehyde by using an excess amount of a basic catalyst.
    Type: Application
    Filed: December 29, 1999
    Publication date: October 11, 2001
    Inventor: JIANJUN LI
  • Patent number: 6288209
    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: September 21, 2000
    Date of Patent: September 11, 2001
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Brian J. Jensen
  • 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: 6277495
    Abstract: A polyimide film of birefringence less than 0.01 is formed by drawing a copolymerized polyimide comprising a block component and a random component which are molecularly bonded, wherein the block component of copolymerized polyimide comprises an aromatic diamine compound having a rigid structure and an aromatic tetracarboxylic acid compound and wherein the random component of copolymerized polyimide comprises an aromatic diamine compound having a flexible structure and at least two aromatic tetracarboxylic acid components. The resulting polyimide film has high elasticity, a low thermal expansion equivalent to that of metal and low water absorbing properties. A method for its manufacture and a metal laminated plate having improved curl properties in which the polyimide is used as the base material are also disclosed.
    Type: Grant
    Filed: July 14, 1998
    Date of Patent: August 21, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Koichi Sawasaki, Kenji Uhara, Michihiro Kubo
  • Patent number: 6274695
    Abstract: The present invention relates to a treating agent for liquid crystal alignment, which is an agent for liquid crystal alignment to be used for a method in which polarized ultraviolet rays or electron rays are irradiated on a polymer thin film formed on a substrate in a predetermined direction relative to the substrate plane, and said substrate is used for aligning liquid crystal without rubbing treatment, wherein said agent for liquid crystal alignment contains a polymer compound having photochemically reactive groups in the polymer main chain and a glass transition temperature of at least 200° C.
    Type: Grant
    Filed: November 1, 1999
    Date of Patent: August 14, 2001
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Hideyuki Endou, Takayasu Nihira, Hiroyoshi Fukuro
  • 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: 6268460
    Abstract: The present invention provides a process for preparing an optical alignment layer for aligning liquid crystals and liquid crystal displays comprising exposing polyimide layers with polarized light. The invention further describes optical alignment layers, liquid crystal displays incorporating optical alignment layers and novel polymer compositions within the class of polyimide, polyamic acids and esters thereof.
    Type: Grant
    Filed: July 18, 2000
    Date of Patent: July 31, 2001
    Inventors: Wayne M. Gibbons, Patricia A. Rose, Paul J. Shannon, Hanxing Zheng
  • Patent number: 6268465
    Abstract: An aliphatic polyester amide which is hydrolysis-resistant includes a ternary polycondensation product of monomeric constituents composed of a monomeric constituent A which is at least one diol having a general formula: HO—R1—OH, where R1 is an aliphatic residue having 2-16 carbon atoms; a monomeric constituent B which is at least one dicarboxylic acid having a general formula: HOOC—R2—COOH, where R2 is an aliphatic residue having 1-14 carbon atoms; and a monomeric constituent C which is at least one diamine having a general formula: H2N—R3—NH2, where R3 is an aliphatic residue having 2-16 carbon atoms and is present in an amount of up to about 5% by weight based on total weight of the monomeric constituents, wherein polycondensation proceeds in the presence of a catalyst comprised of constituent D, which is a metal-containing catalyst, in combination with constituent E, which is at least one of an organic phosphorus compound and an inorganic phosphorus compound, and wherei
    Type: Grant
    Filed: April 12, 1999
    Date of Patent: July 31, 2001
    Assignee: BK Giulini Chemie GmbH Co OHG
    Inventors: Gudrun Chomiakow, Hasan Ulubay, Emil Wilding
  • 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: 6265520
    Abstract: Disclosed is a solvent soluble polyimide and a method for making thereof, which characterizes by producing a solvent soluble polyimide with low electric conductivity through the polymerization of an anhydride and a diamine under the condition with or without catalyst.
    Type: Grant
    Filed: November 29, 1999
    Date of Patent: July 24, 2001
    Assignee: Industrial Technology Research Institute
    Inventors: Hui-Lung Kuo, Chein-Dhau Lee, Yi-Chun Liu, Shih-Chi Yang
  • Patent number: 6262223
    Abstract: Addition-cured polyimides that contain the reaction product of an aromatic triamine or trianhydride analogue thereof, a reactive end group such as 5-norbornene-2, 3-dicarboxylic acid, ester derivatives of 5-norbornene-2,3-dicarboxylic acid, anhydride derivatives of 5-norbornene-2,3-dicarboxylic acid, or 4-phenylethynylphthalic anhydride, an aromatic diamine, and a dialkyl ester of an aromatic tetracarboxylic acid. The resultant starlike polyimides exhibit lower melt flow viscosity than its linear counterparts, providing for improved processability of the polyimide. Also disclosed are methods for the synthesis of these polyimides as well as composite structures formed using these polyimides.
    Type: Grant
    Filed: February 1, 2000
    Date of Patent: July 17, 2001
    Assignee: The United States of America as represented by the Administrator of National Aeronautics and Space Administration
    Inventors: Michael A. Meador, Baochau N. Nguyen, Ronald K. Eby
  • 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: 6248480
    Abstract: An electrolyte is provided having a backbone that includes a plurality of aromatic constituents coupled together by at least one atom having a &pgr;-cloud, and in which a halogen atom and an ion exchange group are covalently bound directly to the backbone. Furthermore, the electrolyte is high temperature resistant and may comprise perhalogenated polymers, including perhalogenated polyphenylenes, perhalogenated polyamides, perhalogenated aromatic polyesters, perhalogenated polyimide, etc. Still further, the electrolyte may have acidic groups as ion exchange groups, including sulfonic acid groups, or phosphoric acid groups.
    Type: Grant
    Filed: June 28, 1999
    Date of Patent: June 19, 2001
    Assignee: SRI International
    Inventors: Subhash Narang, Susanna Ventura
  • Patent number: 6248857
    Abstract: An aromatic polycarbodiimide comprising a structure represented by the following formula (1) has excellent low moisture resistance, heat resistance and a low dielectric constant: wherein Q is one selected from the group consisting of —CH2—, m is 0 or 1, A is a divalent organic group having 4 or less carbon atoms, Ph is a phenyl group, X's are a hydrogen atom when Q is and the same or different halogen atoms when Q is —CH2—, and n is an integer of 2 to 300.
    Type: Grant
    Filed: September 23, 1999
    Date of Patent: June 19, 2001
    Assignee: Nitto Denko Corporation
    Inventors: Sadahito Misumi, Akiko Matsumura, Amane Mochizuki, Michio Satsuma, Michie Sakamoto
  • Patent number: 6235868
    Abstract: Polymerisable resins which comprise a porphyrinogenic ring system obtained by the reaction of: (a) one or more compounds selected from the group consisting of pyrrole and N-(lower)alkyl pyrroles, any of which may be optionally substituted, and (b) a C4-C6 saturated alicyclic ketone which is capable of reacting with the 2 or 5 position of the pyrrole ring. Resin coating systems comprising the said resins.
    Type: Grant
    Filed: September 22, 1994
    Date of Patent: May 22, 2001
    Assignee: The Australian National University
    Inventors: James Thomas Guthrie, Richard Allan Morris, He Wei Dong
  • 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: 6235867
    Abstract: The present invention provides a liquid crystal-aligning agent including, as the resin component, a polyimide precursor containing a chemical structure represented by the following formula (1): The present invention further provides a liquid crystal-aligning agent including, the above polyimide precursor and a polyimide precursor represented by the following general formula (2): (wherein Y is a tetravalent aliphatic group, Z is a bivalent aromatic group, and R is H or an alkyl group).
    Type: Grant
    Filed: November 5, 1999
    Date of Patent: May 22, 2001
    Assignee: Sumitomo Bakelite Company Limited
    Inventors: Toshimasa Eguchi, Toshiro Takeda
  • 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: 6222007
    Abstract: High quality films, preimpregnated tape (prepegs) and composites have been fabricated from polyimide precursor “salt-like” solutions. These “salt-like” solutions have a low viscosity (5,000 to 10,000 cp) and a high solids content (50-65% by weight) and can be coated onto reinforcing fiber to produce prepegs with excellent tack and drape at 12-15% residual solvent (˜4-6% water from thermal imidization reaction). The processing of these types of prepegs significantly overcomes solvent removal problems and allows excellent fiber wet out. In addition, the physical characteristics of the polyimide precursor “salt-like” solutions permits processing into high-performance materials through the use of standard prepregging and composite fabrication equipment. The resultant composites are of high quality.
    Type: Grant
    Filed: May 29, 1998
    Date of Patent: April 24, 2001
    Assignee: The United States of America as represented by the National Aeronautics and Space Administration
    Inventors: Roberto J. Cano, Erik S. Weiser, Terry L. St. Clair, Yoshiaki Echigo, Hisayasu Kaneshiro
  • Patent number: 6211326
    Abstract: The invention relates to a process for preparing hydroxyl- and carboxyl-containing polyesterimide resins, comprising as monomeric components: (A) imide-forming compounds having at least two primary amino groups and/or at least two isocyanate groups or imide-forming compounds having at least one primary amino group and/or at least one isocyanate group and at least one further functional group selected from hydroxyl, carboxyl and/or carboxylic anhydride, (B) polycarboxylic acids and/or their anhydrides and/or their esters and (C) polyols, characterized in that (I) component (A) is reacted with part of component (B) to form a polyimide, (II) the polyimide obtained in accordance with stage (I) is reacted with component (C) to form a polyesterimide, and finally (III) the polyesterimide obtained in accordance with stage (II) is reacted with the remaining part of component (B) to form the Also embraced by the invention is the use of the polyesterimides prepared by the process according to the invention as bi
    Type: Grant
    Filed: July 13, 1999
    Date of Patent: April 3, 2001
    Assignee: Schenectady International, Inc.
    Inventors: Brian W. Glasper, Geoffrey C. Rix, Klaus-Wilhelm Lienert
  • 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: 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: 6180746
    Abstract: A polyimide precursor solid residuum is an admixture of an aromatic dianhydride or derivative thereof and an aromatic diamine or dervative thereof plus a complexing agent, which is complexed with the admixture by hydrogen bonding. The polyimide precursor solid residuum is effectively employed in the preparation of polyimide foam and the fabrication of polyimide foam structures.
    Type: Grant
    Filed: May 21, 1999
    Date of Patent: January 30, 2001
    Assignees: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration, Unitika, LTD
    Inventors: Erik S. Weiser, Terry L. St. Clair, Yoshiaki Echigo, Hisayasu Kaneshiro
  • 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: 6160081
    Abstract: The invention relates to a photosensitive polyimide resin composition comprising (A) a polyamic acid having, in its main chain, repeating units formed from a polycondensation product of at least one tetracarboxylic acid or tetracarboxylic anhydride thereof with at least one diamine compound, and having actinic ray-sensitive functional groups at both terminals thereof; (B) a photosensitive auxiliary having a photopolymerizable functional group; (C) a photopolymerization initiator; and (D) a solvent, wherein 1 the polyamic acid is such that when the repeating unit represented by the formula (1) is defined as a unit molecular weight, a unit molecular weight per carboxyl group (unit molecular weight/COOH) falls within a range of from 200 to 300, and 2 the photosensitive resin composition permits the formation of a polyimide film having a residual stress of 40 MPa or lower and a coefficient of thermal expansion of 30 ppm/.degree. C.
    Type: Grant
    Filed: October 30, 1998
    Date of Patent: December 12, 2000
    Assignees: Nippon Zeon Co., Ltd., Fujitsu Limited
    Inventors: Akira Tanaka, Kei Sakamoto, Kenichi Ito, Yasuhiro Yoneda, Kishio Yokouchi, Yasuo Naganuma
  • 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: 6133405
    Abstract: Water soluble polyalkanolamides and a process to prepare same by reacting polycarboxylic acid or its anhydride, ester or halide derivative with at least one alkanolamine and optionally with a polyamine and removing the condensation byproduct water, alcohol or hydrogen halide.
    Type: Grant
    Filed: July 10, 1997
    Date of Patent: October 17, 2000
    Assignee: Hercules Incorporated
    Inventor: Anthony J. Allen
  • 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