From Carboxylic Acid Having Three Or More Carboxylic Acid Groups Or Derivatives Thereof, And An Organic Amine, Or From An Organic Amine Salt Of A Tri-or Higher Carboxylic Acid Patents (Class 528/350)
  • Patent number: 5741599
    Abstract: Aromatic diamines having a carboxylic acid group and various other diamines are reacted with aromatic tetracarboxylic dianhdyrides in organic polar solvents to provide polyimides. Polyimide compositions for electrodeposition which comprise the neutralized salts of the polyimides, water and poor solvents for the polyimides have good keeping quality and when electrodeposited on electrically conductive materials, can form polyimide coats that have high levels of appearance, smoothness and denseness while exhibiting good physical and chemical characteristics in such aspects as heat resistance, electrical insulation and chemical resistance.
    Type: Grant
    Filed: October 10, 1996
    Date of Patent: April 21, 1998
    Assignee: PI Materials Research Laboratory
    Inventors: Yoshihiro Oie, Hiroshi Itatani, Shinichi Furusaki, Yuji Yamazaki, Sadakazu Hokamura
  • Patent number: 5739263
    Abstract: The present invention provides a film adhesive comprising, as the main constituent, a polyimide resin having a glass transition temperature of 350.degree. C. or lower and soluble in organic solvents, which polyimide resin is obtained by reacting at least one of the following acid components (A) and (B)(A) 4,4'-oxydiphthalic acid dianhydride(B) 3,3',4,4'-biphenyltetracarboxylic acid dianhydride and/or 3,3',4,4'-benzophenonetetracarboxylic acid dianhydridewith at least one of the following amine components (C) and (D)(C) a siloxane compound represented by the following general formula (1) and/or 2,2-bis(4-(4-amino-phenoxy)phenyl)propane ##STR1## wherein R.sub.1 and R.sub.2 are each a bivalent aliphatic (C.sub.1-4) or aromatic group; R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each a mono-valent aliphatic or aromatic group; and k is an integer of 1-20,(D) bis(aminophenoxy)benzene and/or dimethylphenylene-diamineto give rise to ring closure of imide, as well as a process for producing said film adhesive.
    Type: Grant
    Filed: January 28, 1994
    Date of Patent: April 14, 1998
    Assignee: Sumitomo Bakelite Company Limited
    Inventors: Tatsuhiro Yoshida, Yoshitaka Okugawa, Toshio Suzuki, Toshiro Takeda, Yushi Sakamoto, Takuya Tochimoto
  • Patent number: 5734008
    Abstract: The polyimide film of this invention is formed from a polyimide, which is prepared by reacting a diamino compound represented by the general formula (1): ##STR1## wherein X represents a hydrocarbon group having 1 to 20 carbon atoms or a sulfur atom; R represents each independently a halogen atom, a hydrocarbon group having 1 to 6 carbon atoms or a halogen-containing hydrocarbon group having 1 to 6 carbon atoms; a represents each independently an integer of 0 to 4;with a tetracarboxylic dianhydride represented by the general formula (2) ##STR2## wherein Y represents a tetravalent organic group having 2 or more carbon atoms.The polyimide film obtained can be applied favorably to a flexible printed circuit board without adhesion layer, a protective coating for electronic parts and electric wires, or a heat resistant adhesive.
    Type: Grant
    Filed: October 23, 1995
    Date of Patent: March 31, 1998
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mika Shirasaki, Youichi Ueda, Mitsuhiro Shibata
  • Patent number: 5731404
    Abstract: A polyimide alignment film based on pyromellitic dianhydride and a bis(4-aminophenoxy) aromatic compound, such as 1,3-bis(4-aminophenoxy)benzene or 1,4-bis(4-aminophenoxy)benzene, providing low tilt angles of from to 2 degrees when used in liquid crystal displays.
    Type: Grant
    Filed: November 1, 1995
    Date of Patent: March 24, 1998
    Assignees: E. I. du Pont de Nemours and Company, Merck Patent GmbH
    Inventors: Brian Carl Auman, Edgar Bohm
  • Patent number: 5731405
    Abstract: A process for inducing pre-tilt in alignment of a liquid crystal medium comprising exposing at least one optical alignment layer, comprising anisotropically absorbing molecules and hydrophobic moieties, 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 the liquid crystal medium at an angle + and -.theta. with respect to the direction of the polarization of the incident light beam and along the surface of the optical alignment layer, and induce a pre-tilt at an angle .PHI. with respect to the surface of the optical alignment layer and applying a liquid crystal medium to said optical alignment layer, is described. The invention also is directed to liquid crystal display elements made by the process of the invention and to novel polyimide compositions that are useful as optical alignment layers in the invention.
    Type: Grant
    Filed: March 29, 1996
    Date of Patent: March 24, 1998
    Assignee: Alliant Techsystems Inc.
    Inventors: Wayne M. Gibbons, Paul J. Shannon, Shao-Tang Sun
  • Patent number: 5723571
    Abstract: A novel polyimide is soluble in organic solvents and excels in heat resistance. The polyimide comprises 95-40 mol % of the repeating unit represented by the formulas (1) and 60-5 mol % of the repeating unit represented by the formula (2) and has a number average molecular weight of 4,000-200,000: ##STR1## wherein X is --SO.sub.2 -- and/or --C(.dbd.O)--OCH.sub.2 CH.sub.2 O--C(.dbd.O)--, Ar is a divalent group containing aromatic rings, and R is an alkylene group having 1-10 carbon atoms or a group: --CH.sub.2 OC.sub.6 H.sub.4 --, and n is an integer of 1-20.
    Type: Grant
    Filed: August 29, 1996
    Date of Patent: March 3, 1998
    Assignee: Tomoegawa Paper Co., Ltd.
    Inventors: Osamu Oka, Takeshi Nishigaya
  • Patent number: 5714566
    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## in the oligomers, wherein Z= ##STR2## .beta.=the residue an organic radical selected from the group consisting of: ##STR3## --O--.O slashed.--COOH, --O--.O slashed.--COX, --X, --O.paren open-st.(R.sub.8 .paren close-st.OH, ##STR4## --O--.O slashed.--NH.sub.2 ; E= ##STR5## R.sub.8 =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.2.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: February 3, 1998
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowtiz, Clyde H. Sheppard
  • Patent number: 5708122
    Abstract: Poly(ester-imides) containing t-butylhydroquinone and trimellitic anhydride as part of the repeat units, as well as other monomers, are useful as molding resins. The polymers have a high glass transition temperature and are particularly useful in applications requiring good wear resistance.
    Type: Grant
    Filed: April 19, 1996
    Date of Patent: January 13, 1998
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Robert Ralph Luise
  • Patent number: 5708128
    Abstract: Novel thermoset polyimide and composite materials comprising the thermoset polyimides and a fibrous reinforcement are prepared according to this invention. The thermoset polyimides are obtained by heat-treating a linear polyamic acid or a linear polyimide prepared by using 4,4'-bis(3-aminophenoxy)biphenyl and pyromellitic dianhydride as essential monomers or by adding 4,4'-diaminodiphenyl ether or 3,3',4,4'-biphenyltetracarboxylic dianhydride to the essential monomers and by end-capping the molecular chain end with an aromatic dicarboxylic anhydride having a carbon-carbon triple bond. The thermoset polyimides have essential excellent properties of thermoplastic polyimide and additionally has enhanced heat resistance and improved mechanical properties. The thermoset polyimide can be used to provide various kinds of composite materials for aircraft matrices, electric and electronic appliances and others.
    Type: Grant
    Filed: June 24, 1996
    Date of Patent: January 13, 1998
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Hideaki Oikawa, Shoji Tamai, Masahiro Ohta, Akihiro Yamaguchi
  • Patent number: 5696235
    Abstract: Novel polyimides which are soluble in various organic solvents and excellent in thermal resistance, processability are disclosed. The polyimides comprise repeating units represented by the following formula (1) and/or (2) and having a number average molecular weight of 4,000-200,000. ##STR1## wherein Ar is a divalent group represented by the following formula (2) or (3): ##STR2## wherein Y is --O--, --CO--, --S--, --SO.sub.2 -- or --C(CH.sub.3).sub.2 --, ##STR3## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each a C.sub.1-4 alkyl group or a C.sub.1-4 alkoxy group, Ra is a divalent group having 2-6 benzene rings, X.sup.1 represents NH, NR (wherein R is a C.sub.1-4 alkyl group or a C.sub.1-4 alkoxy group) or S, Rb is C.sub.2-20 alkylene group, ether group or dimethylsiloxane group, and X.sub.2 represents NH, NR (wherein R is a C.sub.1-4 alkyl group or a C.sub.
    Type: Grant
    Filed: May 17, 1996
    Date of Patent: December 9, 1997
    Assignee: Tomoegawa Paper Co., Ltd.
    Inventors: Osamu Oka, Takeshi Hashimoto, Takeshi Nishigaya
  • Patent number: 5693745
    Abstract: The present method provides a method for preparing the PI varnish which has the steps of: 1) preparing a mixed solution of 60-100% by weight aprotic solvent, and 0-40% by weight aromatic solvent; 2) adding into the mixed solution in a mole ratio of 1:9 two aromatic diamines; and 3) further adding in the mixed solution in a mole ratio of 1:5 two aromatic dianhydrides. Such PI has a suitable thermal expansion coefficient and characteristics different form those of the PI currently in use.
    Type: Grant
    Filed: February 8, 1996
    Date of Patent: December 2, 1997
    Assignee: Industrial Technology Research Institute
    Inventors: Lee-Ching Kuo, Jinn-Shing King, Wen-Yueh Hsu, Yu-Tai Tsai
  • Patent number: 5688906
    Abstract: A method for forming a polyamic acid having nonlinear optical (NLO) or pre-NLO side chains, which method includes the steps of:(1) providing a bis-(aromatic dicarboxylic acid anhydride) containing at least one NLO or pre-NLO side chain having the structure represented by:D-R-Awherein D, R and A form a delocalized resonance configuration in which R is a pi-conjugated non-centrosymmetric moiety, A is hydrogen or an electron withdrawing moiety and D is an electron donating moiety covalently linked to the bis-(aromatic dicarboxylic acid anhydride); and(2) reacting the bis-(aromatic dicarboxylic acid anhydride) with an aromatic diamine to form a polyamic acid having NLO or pre-NLO side chains. Methods for preparing polyamic acids having NLO or pre-NLO side chains by reacting aromatic diamines having NLO or pre-NLO side chains with bis-(aromatic dicarboxylic acid anhydrides) are also disclosed. Methods of forming the polyamic acids into polyimides having NLO side chains are also included.
    Type: Grant
    Filed: August 7, 1995
    Date of Patent: November 18, 1997
    Assignee: Enichem S.p.A.
    Inventors: Kwan-Yue Alex Jen, Kevin Joel Drost
  • Patent number: 5686558
    Abstract: The invention relates to a liquid crystal orientation film having a specific polymer, the main chain of the polymer formed of urea bonds and imide bonds, and a liquid crystal display element incorporating the film. The liquid crystal orientation film does not require high temperature heat treatment when prepared, allowing treatment below about 150.degree. C. Hence, the production of a liquid crystal display element using the liquid crystal orientation film is simplified. Furthermore, other element materials are protected, and the substrate used can be a plastic substrate lower in heat resistance than glass. Moreover, the liquid crystal orientation film is excellent in such properties as liquid crystal orienting capability, heat resistance, transparency, strength and adhesion to the substrate, and has an especially large and stable pre-tilt angle.
    Type: Grant
    Filed: March 29, 1995
    Date of Patent: November 11, 1997
    Assignee: Toray Industries, Inc.
    Inventors: Kazuo Kitamura, Satoshi Okawa
  • Patent number: 5686559
    Abstract: A poly(imide amic ester) having repeating unit of formula (I) and a process for the preparation thereof are provided, wherein formula (I) has the structure ##STR1## wherein Ar is, ##STR2## Ar' is, ##STR3## Ar" is ##STR4## R is selected from the group consisting of CH.sub.3, CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2, CH.sub.2 CH.sub.2 CH.sub.3, CH.sub.2 (CH(CH.sub.3).sub.2 and C(CH.sub.3).sub.3. Further, processes for the preparation of polyimide, polyimide film and polyimide fiber using the above poly(imide amic ester) are provided.
    Type: Grant
    Filed: October 30, 1995
    Date of Patent: November 11, 1997
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Suh Bong Rhee, Myong Hoon Lee, Ji Woong Park
  • Patent number: 5684119
    Abstract: Directly shapeable clear solutions of polyamide imides and a method for preparing same are provided. The solutions are obtained by polycondensation in .gamma.-butyrolactone (.gamma.BL) in substantially stoichiometric proportions between toluylene diisocyanate and an aromatic acid anhydride, and by dilution in (.gamma.BL) to give a solution allowing them to be processed at a later stage. Yarns and fibers made from said solutions are also described.
    Type: Grant
    Filed: June 10, 1994
    Date of Patent: November 4, 1997
    Assignee: Rhone-Poulenc Fibres
    Inventors: Philippe Michaud, Jean Russo
  • Patent number: 5670603
    Abstract: This invention relates to polymers having non-linear optical properties which polymers include fluorene moieties having at least one electron accepting group and at least one electon donating group substituted to different phenyl rings of the fluorene moiety.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: September 23, 1997
    Assignee: AlliedSignal Inc.
    Inventors: Chengjiu Wu, Jianhui Shan, Ajay Nahata
  • Patent number: 5670609
    Abstract: A polyimide alignment film based on pyromellitic dianhydride and a 2,2'-bis(perfluoroalkoxy)benzidine, as major components, for use in liquid crystal display devices.
    Type: Grant
    Filed: August 8, 1995
    Date of Patent: September 23, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Brian Carl Auman, Edgar Bohm
  • Patent number: 5668247
    Abstract: The invention provides novel thermoplastic polyimide featuring solid adhesive property under low temperature, low hygroscopic coefficient, and solid resistivity to radioactive rays. The invention also provides novel polyamide acid which is substantially precursor of the thermoplastic polyimide, and also provides novel thermally fusible laminated film for covering conductive wires, featuring solid adhesive property under low temperature, solid resistivity to radioactive rays, and distinct suitability for covering superconductive wires in particular.The novel thermoplastic polyimide is represented by general formula (1) corresponding to the chemical structure shown below; ##STR1## wherein, Ar.sub.1, Ar.sub.2, Ar.sub.4, and Ar.sub.6, respectively designate divalent organic radical, whereas Ar.sub.3 and Ar.sub.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: September 16, 1997
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hiroyuki Furutani, Kazuhisa Danno, Yoshifumi Okamoto, Junya Ida, Yoshihide Oonari, Hitoshi Nojiri, Hirosaku Nagano
  • Patent number: 5665856
    Abstract: A diaminobenzene derivative of the formula (I): ##STR1## wherein each of P and Q which may be the same or different from each other, is a single bond, or a bivalent organic group selected from the group consisting of --O--, --COO-- and --CONH--, R.sub.1 is a C.sub.2-22 straight chain alkylene group, and R.sub.2 is a cyclic group selected from the group consisting of an aromatic ring, an aliphatic ring, a heterocyclic ring and substituted forms of such rings.
    Type: Grant
    Filed: April 25, 1995
    Date of Patent: September 9, 1997
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Takayasu Nihira, Yoshio Miyamoto, Hideyuki Endo, Toyohiko Abe
  • Patent number: 5663287
    Abstract: The present invention provide a novel polyimide which is soluble in organic solvents and excels in heat resistance, and to a process for producing the polyimide. The polyimide of the present invention comprises a repeating unit represented by the formula (1) and having a number average molecular weight of from 4,000 to 200,000. ##STR1## wherein X is --SO.sub.2 -- or --C(.dbd.O)--OCH.sub.2 CH.sub.2 O--C(.dbd.O)--, and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
    Type: Grant
    Filed: March 1, 1996
    Date of Patent: September 2, 1997
    Assignee: Tomoegawa Paper Co., Ltd.
    Inventors: Osamu Oka, Takeshi Hashimoto, Takeshi Nishigaya, Tatsuya Hariko
  • Patent number: 5654396
    Abstract: We achieve solvent resistance and extended use life for advanced polyimides by including at least some solvent-resistant linkages in the backbone in place of phenoxyphenyl sulfone linkages and using diPEPA or PEPA crosslinking end caps.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: August 5, 1997
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 5648451
    Abstract: A process for producing a photosensitive resin, comprises reacting a diamine with a tetracarboxylic acid tetraester represented by the formula (1) at a temperature of 0.degree. to 50.degree. C. in an aprotic polar solvent: ##STR1## wherein R.sub.1 is a tetravalent organic group; R.sub.2 is a group represented by the formula: ##STR2## in which R.sub.5 is a divalent to hexavalent organic group, R.sub.6 is H or CH.sub.3 and p is an integer of 1 to 5; R.sub.3 is a group represented by --OCH.sub.3, --OC.sub.2 H.sub.5, --OC.sub.3 H.sub.7 or the formula: ##STR3## and R.sub.4 is a group of the formula: ##STR4## the tetracarboxylic acid tetraester of the formula (1) is obtained by subjecting to addition reaction a tetracarboxylic dianhydride, an alcohol compound represented by the formula R.sub.2 H in which R.sub.2 is as defined above and an alcohol compound represented by the formula R.sub.3 H in which R.sub.
    Type: Grant
    Filed: October 10, 1995
    Date of Patent: July 15, 1997
    Assignee: Sumitomo Bakelite Company Limited
    Inventors: Nobuyuki Sashida, Toshio Banba, Naoshige Takeda
  • Patent number: 5646236
    Abstract: Polyesters obtained by reacting from 5 to 50 parts of at least one linear or branched, aliphatic or cycloaliphatic, at least dihydric alcohol, from 2 to 40 parts of at least one at least dibasic, aromatic carboxylic acid, from 0 to 40 parts of at least one 2-alkenyldicarboxylic anhydride, from 10 to 30 parts of at least one at least dibasic, linear or branched, aliphatic carboxylic acid, from 0 to 15 parts of an aliphatic, linear or branched hydroxy acid, from 0 to 15 parts of an aliphatic, linear or branched polyamine having at least one primary and at least one secondary or tertiary amino group, from 0 to 15 parts of a glycidyl ester of a branched, aliphatic monocarboxylic acid or of a glycidyl ether of a branched, aliphatic alcohol, and from 0 to 15 parts of polyhydroxyamine are useful, for example, as additives in coating compositions.
    Type: Grant
    Filed: January 30, 1995
    Date of Patent: July 8, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Markus A. Schafheutle, Achim Voelker, Susanne Wehner, Gerd Walz, Joachim Zoeller
  • Patent number: 5643998
    Abstract: A recyclable polymer is formed of a plurality of oligomer units obtained by polymerizing a fixed number of monomers, and linkage units for linking the oligomer units through a chemical bond which is different from a bond between monomers constituting the oligomer units, thereby allowing repetitive scission and re-bonding of the linkage units by a predetermined treatment not cleaving the bond between monomers. The recyclable polymer is decomposable into oligomers and the oligomers can be linked again into the original polymer without degrading the quality of the polymer. A process for producing the recyclable polymer, a method for recovering the recyclable polymer, and a method for regenerating the recyclable polymer are also provided.
    Type: Grant
    Filed: March 8, 1995
    Date of Patent: July 1, 1997
    Assignee: Kabushiki Kaisha Toyota Chuo Kenkyusho
    Inventors: Mitsuru Nakano, Arimitsu Usuki, Akane Okada, Osami Kamigaito
  • Patent number: 5644022
    Abstract: Polyimide copolymers were prepared by reacting different ratios of 3,4'-oxydianiline (ODA) and 1,3-bis(3-aminophenoxy)benzene (APB) with 3,3',4,4'-biphenylcarboxylic dianhydride (BPDA), and terminating with an effective amount of a reactive endcapper. The reactive endcappers employed include 4-phenylethynyl phthalic anhydride (PEPA), 3-aminophenoxy-4'-phenylethynylbenzophenone (3-APEB), maleic anhydride (MA) and nadic anhydride (5-norbornene-2,3-dicarboxylic anhydride) (NA). Within a relatively narrow ratio of diamines, from .sup..about. 50% ODA/50% APB to .sup..about. 95% ODA/5% APB, the copolyimides prepared with BPDA and terminated with reactive endgroups have a unique combination of properties that make them very attractive for a number of applications. This unique combination of properties includes low pressure processing (200 psi and below), long term melt stability (several hours at 300.degree. C.
    Type: Grant
    Filed: February 14, 1995
    Date of Patent: July 1, 1997
    Assignee: The United States of America as represented by the Admninistrator of the National Aeronautics and Space Administration
    Inventor: Brian J. Jensen
  • Patent number: 5644016
    Abstract: Use of a polymer containing maleimide units of the formula I ##STR1## in which R.sup.1 is hydrogen, an acyclic or cyclic, aliphatic, aromatic or araliphatic radical which is chiral or achiral, can be monosubstituted or polysubstituted by functional groups and in which one or more CH.sub.2 groups can be replaced by functional groups, as alignment layer in liquid-crystal displays.Alignment layers containing a polymer conforming to the formula I effect, in particular, a suppression of twist states and ghost images and thus an improvement in the optical contrast.
    Type: Grant
    Filed: November 17, 1994
    Date of Patent: July 1, 1997
    Inventors: Horst Roschert, Norbert Rosch, Peter Wegener
  • Patent number: 5639850
    Abstract: A process for preparing a tough, soluble, aromatic, thermoplastic copolyimide is provided. The process comprises the steps of (a) providing 4,4'-oxydiphthalic anhydride to 3,4,3',4'-biphenyltetracarboxylic dianhydride at a mole ratio ranging from about 25 mole percent to 75 mole percent to 75 mole percent to about 25 mole percent; (b) adding 3,4'-oxydianiline to form a mixture; c) adding a polar aprotic or polar protic solvent to the mixture to form a solution having a percentage of solids capable of maintaining polymer solubility; (d) stirring the solution to allow it to react; (e) adding an azeotropic solvent to the solution and heating to remove water; (f) cooling the solution of step (e) to room temperature and recovering the tough, soluble, aromatic, thermoplastic copolyimide.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: June 17, 1997
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Robert G. Bryant
  • Patent number: 5637672
    Abstract: Polyamide esters which can be prepared from tetracarboxylic dianhydrides and can be converted into polyimides by alcohol cleavage with cyclization, characterized in that the radicals OR of the ester groups --COOR which are substituted during the polyimide formation are alkoxy radicals having 2 to 5 C atoms which are monosubstituted or polysubstituted by fluorine.Polyimides prepared therefrom are suitable as orientation layers in liquid-crystal display elements and in optical wave guides.
    Type: Grant
    Filed: April 18, 1991
    Date of Patent: June 10, 1997
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Bernhard Rieger, Ekkehard Bartmann, Eike Poetsch
  • Patent number: 5621068
    Abstract: A thermoplastic polyimide film comprising a thermoplastic polyimide polymer, a polyimide laminate, respectively being suited for use as cover-lay adhesive agent and a cover-lay film capable of exerting distinguished thermal resistant property, processability and adhesion property useful for the manufacture of flexible printed circuit boards, and yet, suited for use as the adhesive-agent layers of flexible copper-coated laminates and bilateral adhesive sheets; and a method of manufacturing the polyimide laminate. The thermoplastic polyimide polymer represented by the general formula (1) specified below: ##STR1## wherein Ar.sub.1, Ar.sub.2, Ar.sub.4 and Ar.sub.6, represents divalent organic radical, whereas Ar.sub.3 and Ar.sub.5 represent quadrivalent organic radical, wherein l, m amd n designate positive integer of 0 to 15, wherein the sum of 1 and m is 1 or more than 1, and wherein t designates positive integer of 1 or more than 1.
    Type: Grant
    Filed: February 22, 1995
    Date of Patent: April 15, 1997
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yoshifumi Okamoto, Hiroyuki Furutani, Kazuhisa Danno, Junya Ida, Hirosaku Nagano
  • Patent number: 5621067
    Abstract: Wholly aromatic polyamides and their shaped articles containing at least 85 mole percent of repeat units of m-phenylene isophthalamide: ##STR1## and repeat units of selected aromatic diamines and diacid chlorides exhibit improved flame resistance while retaining good thermal stability.
    Type: Grant
    Filed: March 30, 1995
    Date of Patent: April 15, 1997
    Assignee: Industrial Technology Research Institute
    Inventors: Jin-Chyueh Lin, Jen-Chang Yang, Ting-Hsiu Chen
  • Patent number: 5614606
    Abstract: Polyamic acids and corresponding polyimides are prepared by reacting polyfunctional amines, aromatic polyfunctional anhydrides or esters thereof, and allyl-nadic anhydride end capping agents, the resulting products exhibiting excellent properties and being suitable for the preparation of prepregs, composites, adhesives, coatings, and the like.
    Type: Grant
    Filed: December 31, 1986
    Date of Patent: March 25, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Mohammad A. Chaudhari, John J. King, Byung Lee
  • Patent number: 5614607
    Abstract: The invention provides a method of preparing a polyimide by reacting together a dianhydride and a diisocyanate or equivalent, the polyimide having repeating units of the general formula (I): ##STR1## in which D is a group comprising one or more aromatic rings, to which the imide carbon atoms are directly bonded, andE is a group comprising one or more cycloaliphatic or aromatic rings, to which the imide nitrogen atoms are bonded directly or via an aliphatic group, provided that the imide nitrogen atoms are not bonded directly to an aromatic ring. Such polyimide is colourless or of low colour.
    Type: Grant
    Filed: March 30, 1995
    Date of Patent: March 25, 1997
    Assignee: Kabushiki Kaisha Kobe Seiko Sho
    Inventors: John N. Hay, Barry Woodfine
  • Patent number: 5612450
    Abstract: A liquid crystal aligning agent comprising a polyamic acid containing an aliphatic and/or alicyclic hydrocarbon group and a polyimide containing an aliphatic and/or alicyclic hydrocarbon group; and a liquid crystal display device using the liquid crystal aligning agent. This liquid crystal aligning agent gives a liquid crystal aligning film which has good liquid crystal aligning property and in which pretilt angle can be changed by radiation with a small energy and which is suitable for domain-divided alignment type liquid crystal display having a wide view angle.
    Type: Grant
    Filed: May 16, 1995
    Date of Patent: March 18, 1997
    Assignees: Japan Synthetic Rubber Co., Ltd., Sharp Corporation
    Inventors: Shigeaki Mizushima, Noriko Watanabe, Hiroko Iwagoe, Seiji Makino, Sigeo Kawamura, Yusuke Tsuda, Nobuo Bessho
  • Patent number: 5610265
    Abstract: A rigid-rod aromatic polyimide having repeating units of the formula: ##STR1##
    Type: Grant
    Filed: February 2, 1996
    Date of Patent: March 11, 1997
    Assignee: The United States of America as represented by The Secretary of the Air Force
    Inventor: Loon-Seng Tan
  • Patent number: 5608033
    Abstract: A liquid crystal alignment film made of a polyimide which has, on its side chain, a benzene or biphenyl ring substituted by a monovalent substituent having a positive value as the .sigma.p value under Hammett's rule.
    Type: Grant
    Filed: May 5, 1995
    Date of Patent: March 4, 1997
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Takayasu Nihira, Yoshio Miyamoto, Hideyuki Endo, Toyohiko Abe
  • Patent number: 5606014
    Abstract: Controlled molecular weight imide oligomers and co-oligomers containing pendent phenylethynyl groups (PEPIs) and endcapped with nonreactive or phenylethynyl groups have been prepared by the cyclodehydration of the precursor amide acid oligomers or co-oligomers containing pendent phenylethynyl groups and endcapped with nonreactive or phenylethynyl groups. The amine terminated amide acid oligomers or co-oligomers are prepared from the reaction of dianhydride(s) with an excess of diamine(s) and diamine containing pendent phenylethynyl groups and subsequently endcapped with a phenylethynyl phthalic anhydride or monofunctional anhydride. The anhydride terminated amide acid oligomers and co-oligomers are prepared from the reaction of diamine(s) and diamine containing pendent phenylethynyl group(s) with an excess of dianhydride(s) and subsequently endcapped with a phenylethynyl amine or monofunctional amine. The polymerizations are carried out in polar aprotic solvents such as under nitrogen at room temperature.
    Type: Grant
    Filed: August 4, 1995
    Date of Patent: February 25, 1997
    Assignee: The United States of America as represented by the United States National Aeronautics and Space Administration
    Inventors: John W. Connell, Joseph G. Smith, Jr., Paul M. Hergenrother
  • Patent number: 5606013
    Abstract: Polyamic acids and corresponding polyimides are prepared by reacting phenylindane diamines, aromatic polyfunctional anhydrides or esters thereof, and nadic anhydride or allylnadic anhydride end capping agents, the resulting products exhibiting excellent properties and being suitable for the preparation of prepregs, composites, adhesives, coatings, and the like.
    Type: Grant
    Filed: December 31, 1986
    Date of Patent: February 25, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Mohammad A. Chaudhari, John J. King, Byung Lee
  • Patent number: 5596073
    Abstract: The present invention relates to solutions which can be directly shaped in anhydrous dimethylalkyleneurea, based on a polyimide obtained from an aromatic dianhydride and an aromatic diisocyanate.It also relates to the process for the production of the above solutions, as well as to a process for spinning these solutions and to the yarns and fibres thus obtained.
    Type: Grant
    Filed: April 14, 1995
    Date of Patent: January 21, 1997
    Assignee: S.N.C. Kermel
    Inventors: Philippe Michaud, Jean Russo
  • Patent number: 5587452
    Abstract: The invention relates to a polyamide-imide containing recurring units according to the formula ##STR1## where Y is an arylene group, andR and R' are alkylene groups, in which at least 50 mole % of R and/or R' is a butylene group.The polyamide-imides are semi-crystalline.They are suitable for injection moulding applications, structural moulded parts, films, coatings and fibres. They can preferably be used in fields of application where temperatures above 200.degree. C. occur.
    Type: Grant
    Filed: July 3, 1995
    Date of Patent: December 24, 1996
    Assignee: DSM N.V.
    Inventors: Cornelis E. Koning, Lilian M. J. Teuwen
  • Patent number: 5580950
    Abstract: A class of soluble polymers having a rigid rod backbone, which when used to cast films, undergo a self-orientation process whereby the polymer backbone becomes more or less aligned parallel to the film surface. This in-plane orientation results in a film that displays negative birefringence. The degree of in-plane orientation and thus, the magnitude of the negative birefringence is controlled by varying the backbone linearity and rigidity of the class of polymers which includes polyesters, polyamides, poly(amide-imides) and poly(ester-imides) through selection of substituents in the polymer backbone chain. By increasing the polymer backbone linearity and rigidity, the degree of in-plane orientation and associated negative birefringence can be increased, and that conversely, by decreasing the polymer backbone linearity and rigidity, the negative birefringence can be decreased.
    Type: Grant
    Filed: October 13, 1994
    Date of Patent: December 3, 1996
    Assignee: The University of Akron
    Inventors: Frank W. Harris, Stephen Z. D. Cheng
  • Patent number: 5578696
    Abstract: A heat-resistant adhesive film, an adhesion structure obtained using the same, and an adhesion method using the same are disclosed, the film comprising a polyisoimide resin containing at least 40 mol % of an isoimide unit represented by formula (I): ##STR1## wherein R.sub.1 represents a tetravalent aromatic or aliphatic residue; R.sub.2 represents a divalent aromatic or aliphatic residue; and the arrow represents a bond replaceable on isomerization, in the molecule thereof. The isoimide unit of the polyisoimide resin is easily converted to an imide unit on heating, e.g., hot pressing with an adherend, to provide a cover-lay film or a single-sided or double-sided base for printed circuit boards having excellent adhesion, heat resistance, dimensional precision, and workability.
    Type: Grant
    Filed: April 6, 1994
    Date of Patent: November 26, 1996
    Assignee: Nitto Denko Corporation
    Inventors: Amane Mochizuki, Kazumi Higashi, Masako Maeda
  • Patent number: 5569510
    Abstract: Process for the production of polyester resins suitable for the manufacture of fibers including a phase of esterification of an aromatic dicarboxylic acid with an alkylenic glycol or of transesterification of a diester of the dicarboxylic acid with the alkylenic glycol, of polycondensation of diester obtained to form a prepolymer with intrinsic viscosity between 0.2 and 0.5 dl/g and, lastly, of polycondensation of the melt polymeric mass added with a dianhydride of a tetracarboxylic acid kept in agitation and on which an inert gas current is circulated.
    Type: Grant
    Filed: April 11, 1994
    Date of Patent: October 29, 1996
    Assignee: Sinco Engineering S.p.A.
    Inventors: Hussain A. K. Al Ghatta, Mario Pizzetti
  • Patent number: 5567800
    Abstract: Controlled molecular weight phenylethynyl terminated imide oligomers (PETIs) have been prepared by the cyclodehydration of precursor phenylethynyl terminated amic acid oligomers. Amino terminated amic acid oligomers are prepared from the reaction of dianhydride(s) with an excess of diamine(s) and subsequently endcapped with phenylethynyl phthalic anhydride(s) (PEPA). The polymerizations are carried out in polar aprotic solvents such as N-methyl-2-pyrrolidinone or N,N-dimethylacetamide under nitrogen at room temperature. The amic acid oligomers are subsequently cyclodehydrated either thermally or chemically to the corresponding imide oligomers. Direct preparation of PETIs from the reaction of dianhydride(s) with an excess of diamine(s) and endcapped with phenylethynyl phthalic anhydride(s) has been performed in m-cresol. Phenylethynyl phthalic anhydrides are synthesized by the palladium catalyzed reaction of phenylacetylene with bromo substituted phthalic anhydrides in triethylamine.
    Type: Grant
    Filed: October 28, 1994
    Date of Patent: October 22, 1996
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Paul M. Hergenrother, Joseph G. Smith, Jr.
  • Patent number: 5539080
    Abstract: A process is disclosed for making circuit elements by photolithography comprising depositing an antireflective polyimide or polyimide precursor layer on a substrate and heating the substrate at 200.degree. C. to 500.degree. to provide a functional integrated circuit element that includes an antireflective polyimide layer. The antireflective polyimide layer contains a sufficient concentration of at least one chromophore to give rise to an absorbance sufficient to attenuate actinic radiation at 405 or 436 nm. Preferred chromophores include those arising from perylenes, naphthalenes and anthraquinones. The chromophore may reside in a dye which is a component of the polyimide coating mixture or it may reside in a residue which is incorporated into the polyimide itself.
    Type: Grant
    Filed: April 19, 1995
    Date of Patent: July 23, 1996
    Assignee: International Business Machines Corporation
    Inventors: Dennis P. Hogan, Harold G. Linde, Ronald A. Warren
  • Patent number: 5532334
    Abstract: A process for preparing polyamideimide resins having high molecular weights as described wherein major problems of prior art processes such as low heat resistance and low melt flowability are improved. Polyamideimide resins having an intrinsic viscosity of 0.4 to 1.50 dl/g as measured on a solution of dimethylacetamide as a solvent at a concentration of 0.5 g/dl at 30.degree. C., are prepared by reacting an aromatic tricarboxylic acid anhydride with an aromatic diamine in N-methyl pyrrolidone solvent in the presence of a first catalyst selected from a group consisting of thionyl chloride, p-toluenesulphonly chloride, sulfuryl chloride, cyanuric chloride and phosphorus trichloride at a temperature of 50.degree. C. to 130.degree. C. over a period of 1 to 5 hours and further reacting the resultant reaction mixture in the presence of a second catalyst which is a compound of the formula (RO).sub.
    Type: Grant
    Filed: November 14, 1994
    Date of Patent: July 2, 1996
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Kil-Yeong Choi, Dong-Hack Suh, Mi-Hie Yi, Young-Taik Hong, Jong-Chan Won
  • Patent number: 5521276
    Abstract: Polyamideimide resins having the formula (I) ##STR1## in which repeating units are bound in a head to tail or head to head manner,R is at least two divalent groups selected from the group consisting of ##STR2## (cis-, trans- conformational mixture) wherein one divalent group is ##STR3## group in a PAI molecule, produced by introducing isophorone diamine into the conventional aromatic polyamideimide resins.
    Type: Grant
    Filed: June 22, 1994
    Date of Patent: May 28, 1996
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Kil-Yeong Choi, Mi-Hie Yi, Jae-Heung Lee, Moon-Young Jin, Young-Taik Hong
  • Patent number: 5517993
    Abstract: Novel compounds having use as contrast agents in magnetic resonance imaging, as well as other uses, are described. The compounds are comprised of a copolymer which comprises at least two of a first monomer of the formula X.sub.1 -(CHR.sub.2 CHR.sub.2 --Y).sub.n --(CHR.sub.2).sub.m --CHR.sub.2 CHR.sub.2 --X.sub.2, wherein X.sub.1 and X.sub.2 are, independently, OH, NH.sub.2, NHR.sub.1, COOH, COOR.sub.1, SH, or Z, Y is O, NH, NR.sub.1, S, or CO, n is 0-10,000, m is 0 or 1, each Z is, independently, Cl, Br, or I, each R.sub.1 is, independently, a C.sub.1 -C.sub.20 substituted alkyl or cycloalkyl, and each R.sub.2 is, independently, H or OH, and at least one of a second monomer which is a polynitrilo chelating agent having at least two COOH, COOR.sub.1, or COZ groups, the first and second monomers being bound to one another to form a copolymer through an ester, amide, or carboxylic thioester linkage of at least one of the OH, NH.sub.2, NHR.sub.1, COOH, COOR.sub.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: May 21, 1996
    Assignee: ImaRx Pharmaceutical Corp.
    Inventors: Evan C. Unger, Guanli Wu
  • Patent number: 5516875
    Abstract: This invention concerns positive-working photodefinable polyimide precursors which make use of chemical amplification based on photoacid catalyzed cleavage of acid labile-poly(amic acetal esters).
    Type: Grant
    Filed: December 15, 1994
    Date of Patent: May 14, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Howard E. Simmons, III
  • Patent number: 5498691
    Abstract: Disclosed are bis-meta-benzotrifluoride compounds having the general formula ##STR1## where each A is independently selected from the group consisting of NO.sub.2, NH.sub.2, and NH.sub.3.sup.+ Z.sup.-, Z.sup.- is an anion and B is selected from the group consisting of O, CO, S, SO, and SO.sub.2. The diamine compounds are useful as monomers in making polyimides, polyamide-imides, and polyamides.
    Type: Grant
    Filed: October 9, 1990
    Date of Patent: March 12, 1996
    Assignee: Occidental Chemical Corporation
    Inventors: Jeffrey S. Stults, Henry C. Lin, Robert A. Buchanan, Robert L. Ostrozynski
  • Patent number: 5496915
    Abstract: Polyimides are obtainable by reacting a dianhydride component with a diamine component, at least one diamine containing cycloaliphatic units, with the proviso that the dianhydride component is a mixture of different dianhydrides if the diamine component consists only of one diamine containing cycloaliphatic units and the diamine component is a mixture of different diamines if the dianhydride component consists of only one dianhydride.
    Type: Grant
    Filed: February 13, 1995
    Date of Patent: March 5, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Christian Fischer, Karin Elbl-Weiser, Ju/ rgen Koch