Reactant Contains Three Or More Carboxylic Acid Groups Or Is Derivative Thereof Patents (Class 528/188)
  • 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: 6210872
    Abstract: A novel optical film capable of readily vitrifying the tendency and state of liquid crystal alignment, excellent in the ability to retain the alignment state, and suitable for the application to optical elements. The film is produced from a liquid-crystal material containing as the essential ingredient a liquid-crystal polyester having structural units (A) and (B) as the essential unit, exhibiting a vitrified state at a temperature lower than the liquid-crystal transition point, and having a logarithmic viscosity number (&eegr;) of 0.04-0.4 dl/g as measured at 30° C. in a phenol/tetrachloroethane solvent (60/40 by weight), wherein each X represents independently O or C═O; each Y represents independently a group selected from among F, Cl, Br and 1-4C alkyls; and n is 0 or 1.
    Type: Grant
    Filed: May 18, 2000
    Date of Patent: April 3, 2001
    Assignee: Nippon Mitsubishi Oil Corporation
    Inventors: Kenji Hosaki, Yoshihiro Kumagai, Tadahiro Kaminade
  • 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: 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: 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: 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: 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: 6103860
    Abstract: There is disclosed an organic optical component prepared from a resin essentially comprising one or more repetitive structural units selected from the group consisting of structures represented by general formula (1); ##STR1## wherein A is either of the groups below. ##STR2## This invention provides an organic optical component with excellent transparency, heat resistance and mechanical strength as well as a low birefringence. This invention also provides a novel aromatic polyamide with a low permitivity and excellent transparency, processability and thermal stability, besides excellent heat resistance inherent in an aromatic polyamide.
    Type: Grant
    Filed: June 14, 1999
    Date of Patent: August 15, 2000
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Wataru Yamashita, Tomomi Yoshimura, Atsushi Shibuya, Yoshihiro Sakata, Hideaki Oikawa, Masahiro Ohta
  • Patent number: 6103864
    Abstract: The polyimides are derived from solutions of at least one low-boiling organic solvent, e.g. isopropanol containing a mixture of polyimide-forming monomers. The monomeric solutions have an extended shelf life at ambient (room) temperatures as high as 80.degree. C. and consist essentially of a mixture of monoalkyl ester-acids, alkyl diester-diacids and aromatic polyamines wherein the alkyl radicals of the ester-acids are derived from lower molecular weight aliphatic secondary alcohols having 3 to 5 carbon atoms per molecule such as isopropanol, secondary butanol, 2-methyl-3-butanol, 2 pentanol or 3-pentanol. The solutions of the polyimide-forming monomers have a substantially improved shelf-life and are particularly useful in the aerospace and aeronautical industry for the preparation of polyimide reinforced fiber composites such as the polyimide cured carbon composites used in jet engines, missiles, and for other high temperature applications.
    Type: Grant
    Filed: January 14, 1999
    Date of Patent: August 15, 2000
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: William B. Alston, Gloria S. Gahn
  • Patent number: 6100371
    Abstract: A polyimide for optical communications has a monomer, represented by the formula (1), as a repeating unit: ##STR1## wherein X.sub.1 and X.sub.2 are independently selected from the group consisting of halogen atom, halogenated alkyl group, halogenated aromatic ring group, --NO.sub.2, --OR.sup.1 and --SR.sup.1 (where R.sup.1 is selected from the group consisting of halogenated alkyl and halogenated aromatic ring groups); and Z is selected from the group consisting of divalent halogenated aliphatic hydrocarbon, divalent halogenated aliphatic cyclic hydrocarbon and divalent halogenated aromatic hydrocarbon. Thus, light absorption loss at a near infrared light wavelength range can be minimized by using the polyimide, so that the polyimide is very useful as an optical material in the optical communications field using light of a near infrared light region.
    Type: Grant
    Filed: September 18, 1998
    Date of Patent: August 8, 2000
    Assignee: SamSung Electronics Co., Ltd.
    Inventors: Dong-Hack Suh, Eun-Young Chung, Tae-Hyung Rhee
  • 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: 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: 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: 6060581
    Abstract: An optical alignment composition including self-photosensitive polyimide having a benzophenone moiety and an active hydrogen moiety, and an LCD having the alignment layer formed of the optical alignment composition are provided. Since the alignment layer with excellent thermal stability and improved pretilt angle is obtained, the LCD having excellent performance can be manufactured.
    Type: Grant
    Filed: December 10, 1997
    Date of Patent: May 9, 2000
    Assignee: Samsung Display Devices Co., Ltd.
    Inventors: Han-sung Yu, Yong-kyu Jang
  • 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: 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: 6048959
    Abstract: Tough, soluble, aromatic, thermoplastic copolyimides were prepared by reacting 4,4'-oxydiphthalic anhydride, 3,4,3',4'-biphenyltetracarboxylic dianhydride and 3,4'-oxydianiline. Alternatively, these copolyimides may be prepared by reacting 4,4'-oxydiphthalic anhydride with 3,4,3',4'-biphenyltetracarboxylic dianhydride and 3,4'-oxydiisocyanate. Also, the copolyimide may be prepared by reacting the corresponding tetra acid and ester precursors of 4,4'-oxydiphthalic anhydride and 3,4,3',4'-biphenyltetracarboxylic dianhydride with 3,4'-oxydianiline. These copolyimides were found to be soluble in common amide solvents such as N,N'-dimethyl acetamide, N-methylpyrrolidinone, and dimethylformamide allowing them to be applied as the fully imidized copolymer and to be used to prepare a wide range of articles.
    Type: Grant
    Filed: January 22, 1999
    Date of Patent: April 11, 2000
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Robert G. Bryant
  • 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
  • Patent number: 6037499
    Abstract: This invention relates the novel diamines, the polyimide oligomers and the polyimides derived therefrom and to the method of preparing the diamines, oligomers and the polyimides. The thermoplastic polyimides derived from the aromatic diamines of this invention are characterized as having a high glass transition temperature, good mechanical properties and improved processability in the manufacture of adhesives, electronic and composite materials for use in the automotive and aerospace industry. The distinction of the novel aromatic diamines of this invention is the 2,2',6,6'-substituted biphenyl radicals which exhibit noncoplanar conformation that enhances the solubility of the diamine as well as the processability of the polyimides, while retaining a realatively high glass transition temperature and improved mechanical properties at useful temperature ranges.
    Type: Grant
    Filed: December 24, 1998
    Date of Patent: March 14, 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: 6031068
    Abstract: The object of the present invention is to provide polyimide composition having such excellent property as low water absorption and low hygroscopic swelling, and a base tape for a TAB carrier tape and a FPC.The another object of the present invention is to provide polyimide composition comprising polyimide consisting of a repeating unit of the general formula (1): ##STR1## The further object of the present invention is to provide a base tape for a TAB carrier tape containing polyimide film made from said polyimide composition as a base film and a FPC containing polyimide film made from said polyimide composition as an insulating material.
    Type: Grant
    Filed: October 23, 1998
    Date of Patent: February 29, 2000
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventor: Kohji Okada
  • Patent number: 6031061
    Abstract: A bis(trisubstitutedtrimellitic anhydride) derivative and a polyesterimide for optical communications, the polyesterimide being formed therefrom. The polyesterimide has a high refractive index, so that when using such polyesterimide as a material for a core of an optical fiber, the range of materials that can be selected for the cladding becomes wide. Also, a coating property and adhesion to a substrate are improved, thereby providing a good film forming property and thermal stability. Also, because the polyesterimide can minimize optical loss at a near infrared wavelength range, the polyesterimide is very useful as an optical material in the optical communications field adopting the light of near infrared wavelength.
    Type: Grant
    Filed: December 31, 1998
    Date of Patent: February 29, 2000
    Assignee: SamSung Electronics Co., Ltd.
    Inventors: Dong-hack Suh, Sun-young Chung, Tae-hyung Rhee
  • Patent number: 6031067
    Abstract: The invention herein relates to a soluble polyimide resin and the process of preparation of the same, wherein aromatic tetracarboxylic dianhydride and aromatic diamine having an alicyclic group with various structures of substituted alkyl groups 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 aromatic diamine monomers having a novel chemical structure with various types of aromatic tetracarboxilic acid 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 250.degree. C..about.400.degree. C. and showed a increase in solubility in proportion to the increase in volume of the alkyl group.
    Type: Grant
    Filed: May 29, 1998
    Date of Patent: February 29, 2000
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Kil-Yeong Choi, Mi-Hie Yi, Wenxi Huang
  • Patent number: 6028159
    Abstract: A polyamideimide for optical communications, having a minimum light absorption loss in a near infrared light wavelength range, high thermal stability and excellent film processibility, and a method for preparing the same are provided. The polyamideimide has a higher refractive index than the conventional fluorinated polyamideimide. Thus, when using such polyamideimide as a material for a core of an optical fiber, the selection range on the material for cladding becomes wide. Also the coating property and adhesiveness to a substrate are improved, thereby providing a good film processibility and heat resistance.
    Type: Grant
    Filed: December 31, 1998
    Date of Patent: February 22, 2000
    Assignees: SamSung Electronics Co., Ltd., Korea Research Institute of Chemical Technology
    Inventors: Dong-hack Suh, Eun-young Chung, Tae-hyung Rhee
  • Patent number: 6025460
    Abstract: The service life of fiber-reinforced polyimide composites in a high temperature oxidative environment is extended by coating with a polyimide coating precursor solution that is synthesized by reacting an aromatic dianhydride with an aromatic diamine in a non-reactive solvent. The reactive solution is heated to a temperature sufficent to reduce its viscosity prior to its use as a coating. Preferably, a mixture of meta-phenylenediamine and para-phenylenediamine is reacted with biphenyldianhydride in n-methyl pyrrolidinone solvent and thereafter heated to between about 50.degree. C. (122.degree. F.) and 150.degree. C. (302.degree. F.) under nitrogen while stirring for a time sufficient to obtain a polyamic acid polyimide precursor coating solution having a Brookfield viscosity of from about 500 to about 5000 cP and a solids content of from about 5 to about 35 weight percent.
    Type: Grant
    Filed: November 4, 1997
    Date of Patent: February 15, 2000
    Assignee: Ohio Aerospace Institute
    Inventors: Anthony M. Mazany, Stanley G. Prybyla
  • Patent number: 6025458
    Abstract: Disclosed are degradable materials including molded products, laminates, foams, nonwoven materials, adhesives, coatings and films, and particularly packaging films. The materials are made using polydioxaneone polymers comprising at least two different dioxaneone-based repeating units. Preferred polymers are polydioxanediones. First repeating units have less carbon atoms in constituent groups extending from the polymer backbone than second repeating units. Physical characteristics and degradation of the materials can be varied by varying the choice and/or relative proportions of first and second repeating units in the polydioxaneone polymers. Methods for preparing polydioxaneone polymers that can be used in the manufacture of the materials are also discussed, as are suitable monomers and methods for preparing such monomers.
    Type: Grant
    Filed: June 15, 1998
    Date of Patent: February 15, 2000
    Assignee: Chronopol, Inc.
    Inventors: Edward S. Lipinsky, Richard G. Sinclair, James D. Browning, Alex Cheung, Kevin H. Schilling, Dan W. Verser
  • Patent number: 6025461
    Abstract: A photosensitive polyimide, which comprises a copolymer of (A) three diamine compounds mixture consisting of a diaminopolysiloxane, a hydroxyl group-containing diamine or carboxyl group-containing diamine and 1,4-bis[2-(3-aminobenzoyl)ethenyl]benzene with (B) an aromatic tetrocarboxylic acid dianhydride or a dicarboxylic anhydride having a 2,5-dioxotetrahydrofuryl group as one acid anhydride group, is soluble in all-purpose low boiling organic solvents, typically methyl ethyl ketone and provides a negative type photosensitive polyimide, which is developable with an aqueous alkaline solution.
    Type: Grant
    Filed: August 5, 1998
    Date of Patent: February 15, 2000
    Assignee: Nippon Mektron, Limited
    Inventors: Lin-Chiu Chiang, Jeng-Tain Lin
  • Patent number: 6013760
    Abstract: The invention herein relates to a soluble polyimide resin for a liquid crystal alignment layer and the process of preparation of the same, wherein aliphatic tetracarboxylic dianhydride and aromatic diamine having the amide group are used to yield a novel form of a polyimide resin having superior heat-resistance, solubility, transparency, and liquid crystal alignment capacity.More specifically, the invention herein relates to a novel polyimide resin having excellent heat-resistance, solubility, liquid crystal alignment property, and high pretilt angle, which is prepared by means of jointly using the aromatic diamine, used for the preparation of the conventional polyimide resin, and the aromatic diamine having a long alkyl chain with a substituted amide group, and reacting the same with various types of carboxylic dianhydride.
    Type: Grant
    Filed: May 29, 1998
    Date of Patent: January 11, 2000
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Kil-Yeong Choi, Mi-Hie Yi, Moon-Young Jin, Dae-Woo Ihm, Jae-Min Oh
  • Patent number: 5986036
    Abstract: A new holographic substrate utilizing flexible, optically transparent fluorinated polyimides. Said substrates have extremely low birefringence which results in a high signal to noise ratio in subsequent holograms. Specific examples of said fluorinated polyimides include 6FDA+APB and 6FDA+4BDAF.
    Type: Grant
    Filed: June 27, 1997
    Date of Patent: November 16, 1999
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Paul A. Gierow, William R. Clayton, Anne K. St. Clair
  • Patent number: 5977289
    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. The present invention is also directed to synthesis of this special dianhydride.
    Type: Grant
    Filed: August 18, 1998
    Date of Patent: November 2, 1999
    Assignee: National Science Council
    Inventors: Chin-Ping Yang, Sheng-Huei Hsiao
  • Patent number: 5969088
    Abstract: An angularity enhancement layer in a liquid crystal display, which display comprises a liquid crystal cell, wherein the angularity enhancement layer includes a negative birefringent polyimide layer comprising a plurality of structural units having pendant fluorene groups, said angularity enhancement layer being disposed on at least one surface of said liquid crystal cell. A liquid crystal display can comprise an angularity enhancement construction of the invention which comprises a polyimide layer.
    Type: Grant
    Filed: May 5, 1998
    Date of Patent: October 19, 1999
    Assignee: 3M Innovative Properties Company
    Inventors: Stephen A. Ezzell, Hassan Sahouani, Ernest L. Thurber
  • Patent number: 5969087
    Abstract: A novel polyimide having a repeating structure unit expressed by the following general formula (1), a method for manufacturing the same, a gas separation membrane using the novel polyimide and the method for manufacturing the same. The gas separation membrane using this polyimide is excellent in gas permeable performance and separation selectivity for gas, for example, carbon dioxide, methane, etc.General Formula (1) ##STR1## where R denotes a quadrivalent organic group.
    Type: Grant
    Filed: March 31, 1998
    Date of Patent: October 19, 1999
    Assignee: Nitto Denko Corporation
    Inventor: Masatoshi Maeda
  • Patent number: 5969079
    Abstract: Thermomechanical and thermo-oxidative stabilities in resin composites across the range of aerospace "engineering thermoplastic" resins are improved by forming four crosslinks at each addition polymerization site in the backbone of the resin using crosslinking functionalities of the general formula: ##STR1## wherein Z= ##STR2## .beta.=the residue an organic radical selected from the group consisting of: ##STR3## R.sub.R =a divalent organic radical; X=halogen;Me=methylT=allyl or methallyl.G=--CH.sub.2 --,--S--, --CO--, --SO--, --O--, --CHR.sub.3 --, or --C(R.sub.3).sub.2 --;i=1 or 2;R.sub.3 =hydrogen, lower alkyl, lower alkoxy, aryl, or aryloxy; and.theta.=--C.tbd.N, --O--C.tbd.N, --S--C.tbd.N, or --CR.sub.3 .dbd.C(R.sub.3).sub.
    Type: Grant
    Filed: October 21, 1994
    Date of Patent: October 19, 1999
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 5965691
    Abstract: A process for aligning liquid crystals adjacent to a surface of an optical alignment layer comprising: exposing at least one optical alignment layer, comprising anisotropically absorbing molecules, to polarized light; the polarized light having a wavelength within the absorption band of said anisotropically absorbing molecules; wherein the exposed anisotropically absorbing molecules induce alignment of a liquid crystal medium at an angle + and - with respect to the direction of the polarization of the incident light beam and along the surface of the optical alignment layer; and applying a liquid crystal medium to said optical alignment layer; wherein said anisotropically absorbing molecules consist essentially of diaryl ketones, is described.
    Type: Grant
    Filed: July 1, 1997
    Date of Patent: October 12, 1999
    Assignee: Elsicon, Inc.
    Inventors: Wayne M. Gibbons, Paul J. Shannon, Shao-Tang Sun
  • Patent number: 5959070
    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: October 24, 1997
    Date of Patent: September 28, 1999
    Assignee: University of Rochester
    Inventors: Samson A. Jenekhe, John A. Osaheni
  • Patent number: 5958292
    Abstract: A polyamic acid derived from an amine component comprising a 2-cyano-1,4-phenylene diamine and a family of diaryl ketones is claimed. The polyamic acids are useful in formation of polyimides, also claimed, and for the optical alignment of liquid crystals and the manufacture of liquid crystal optical elements, also claimed.
    Type: Grant
    Filed: May 18, 1998
    Date of Patent: September 28, 1999
    Assignee: Elsicon Inc.
    Inventors: Wayne M. Gibbons, Paul Joseph Shannon, Hanxing Zheng