Nitrogen-containing Reactant Contains An Amine Group Patents (Class 528/229)
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Patent number: 5459232Abstract: A nonlinear optical material composed of a polyimide obtained from a diamine and/or a diacid anhydride or dithioacid anhydride substituted by a portion having a nonlinear optical effect or of molecules having a benzocyclobutene structure substituted at the portions having an nonlinear linear optical effect.Type: GrantFiled: July 9, 1993Date of Patent: October 17, 1995Assignee: Fujitsu LimitedInventors: Wataru Sotoyama, Satoshi Tatsuura, Tetsuzo Yoshimura, Azuma Matsuura, Tomoaki Hayano
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Patent number: 5457154Abstract: A moldable polyimide resin composition which has melt-flowability and excellent processability in addition to essential heat-resistant of polyimide and comprises an aromatic bisimide compound and polyimide resin. A further aspect relates to a carbon fiber reinforced polyimide resin composition which has excellent mechanical strengths and comprises a carbon fiber coated with aromatic bisimide compound on the surface and the polyimide resin. A still further aspect relates to a novel bisimide compound which is very useful as the aromatic bisimide compound in the composition.Type: GrantFiled: November 9, 1992Date of Patent: October 10, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Masahiro Ohta, Akio Matsuyama, Eiji Senoue, Fumiaki Kuwano, Osamu Yasui, Yasunori Yoshida, Akinori Ryu, Tadashi Kobayashi
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Patent number: 5455327Abstract: Two monomers containing meta-biphenylenedioxy moieties were prepared. One monomer, a diamine, is used to prepare polyimide, polyamide, and epoxy polymers. The other monomer, a dianhydride, was used to prepare polyimide polymers. These polymers are used to make films, coatings, and selective membranes.Type: GrantFiled: December 16, 1993Date of Patent: October 3, 1995Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Terry L. St. Clair, J. Richard Pratt
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Patent number: 5453326Abstract: The present invention relates to a polymeric film in-line coated with polyamido-polyethyleneimine to render the film receptive to direct extrusion coating with other polymers or to ink adhesion and to a method of making the same. Additionally, the present invention relates to an oriented polymeric film which has been in-line coated with polyamido-polyethyleneimine so that it has anti-static properties for other packaging applications.Type: GrantFiled: December 22, 1994Date of Patent: September 26, 1995Inventor: Junaid A. Siddiqui
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Patent number: 5453484Abstract: A diamine compound of the general formula ##STR1## wherein the arrows denote isomerism, R.sub.1 is a divalent aromatic group selected from the group consisting of ##STR2## R.sub.2 is a tetravalent aromatic group selected from the group consisting of ##STR3## and R.sub.4 is a monovalent aliphatic group selected from the group consisting of ethyl and isopropyl; and, a process for preparing same.Type: GrantFiled: June 30, 1994Date of Patent: September 26, 1995Assignee: Korea Research Institute of Chemical TechnologyInventors: Suh Bong Rhee, Ji Young Chang, Bong Seok Moon, Ji-Woong Park
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Patent number: 5449742Abstract: Polyimide optical waveguide structures comprising a core within a cladding wherein at least one of the core and the cladding is a polyimide containing 6FDA, BTDA, an aromatic diamine having bulky methyl groups ortho to the amine, and a co-diamine wherein the polyimides have the properties of low optical loss, low optical absorbance, controllable refractive index, and high thermal stability, and wherein the polyimides are photosensitive and solvent resistant.Type: GrantFiled: February 15, 1994Date of Patent: September 12, 1995Assignee: Amoco CorporationInventors: Allyson J. Beuhler, David A. Wargowski
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Patent number: 5449741Abstract: A polyimide optical material, composed of a perfluorinated polyimide having a perfluorinated repeating unit represented by general formula (1) ##STR1## wherein R.sub.1 is a tetravalent perfluorinated organic group; and R.sub.2 is a divalent perfluorinated organic group.Type: GrantFiled: October 25, 1993Date of Patent: September 12, 1995Assignee: Nippon Telegraph and Telephone CorporationInventors: Shinji Ando, Toru Matsuura, Shigekuni Sasaki, Fumio Yamamoto
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Patent number: 5446074Abstract: New photosensitive polyamic acid precursors are disclosed which have the formula: ##STR1## where Z is a tetravalent organic radical which contains at least one aromatic ring, Z' is a divalent organic radical which contains at least one aromatic ring, and R* is a photosensitive group. Particularly preferred compounds include BPDA-PDA and BPDA-ODA polyamic acid precursors. The precursor compositions within the practice of this invention are i-line, g-line, and i-/g-line active and show good photoresolution. The films formed exhibit excellent self-adhesion and adhesion to glass ceramic and silicon wafer substrates have low internal stress, a very low degree of solvent swelling, high thermal stability, and excellent mechanical properties such as high modulus/tensile strength and high elongation at break.Type: GrantFiled: December 17, 1993Date of Patent: August 29, 1995Assignee: International Business Machines CorporationInventors: George Czornyj, Moonhor Ree, Willi Volksen, Dominic C. Yang
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Patent number: 5442002Abstract: A polymer scale deposition preventive agent for use in polymerization of a monomer having an ethylenically unsaturated double bond, comprising an alkaline solution containing a condensation product of (A) a diphenyl compound having at least two amino groups and (B) a quinone compound. When the aforementioned monomer is polymerized in a polymerization vessel having a coating formed by applying the aforementioned preventive agent to inner wall surfaces followed by drying, polymer scale can be effectively prevented from being deposited not only on the areas located in the liquid-phase region but also on the areas around the interface between the gas and liquid phases in the polymerization vessel. When an obtained polymer is formed into a sheet or the like, it is possible to obtain a formed product having few fish eyes and good initial coloration.Type: GrantFiled: July 21, 1994Date of Patent: August 15, 1995Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Toshihide Shimizu, Mikio Watanabe
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Patent number: 5442030Abstract: Polyimides are made from the novel diamines 1,2-bis(3-aminophenyl)perfluorocyclobutane, 1,2-bis(3- or 4-aminophenyl)perfluorocyclobutene, -cyclopentene and -cyclohexene, by reaction with aromatic carboxylic anhydrides. The polyimides are useful for coatings and films.Type: GrantFiled: October 14, 1993Date of Patent: August 15, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Zhenyu Yang
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Patent number: 5442031Abstract: Soluble polyimides are formed from oxydiphthalic anhydride and 2,4-diaminotoluene. Optionally, up to 30 mole % of an alternate diamine and up to 50 mole % of an alternate dianhydride can be used with the oxydiphthalic anhydride and 2,4-diaminotoluene.Type: GrantFiled: April 21, 1994Date of Patent: August 15, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Beth E. Dunlap
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Patent number: 5438082Abstract: In order to produce a polymer electrolyte membrane from sulfonated, aromatic polyether ketone, an aromatic polyether ketone of the formula (I) ##STR1## in which Ar is a phenylene ring having p- and/or m-bonds,Ar' is a phenylene, naphthylene, biphenylene, anthrylene or another divalent aromatic unit,X, N and M, independently of one another are 0 or 1,Y is 0, 1, 2 or 3,P is 1, 2, 3 or 4,is sulfonated and the sulfonic acid is isolated. At least 5% of the sulfonic groups in the sulfonic acid are converted into sulfonyl chloride groups, and these are reacted with an amine containing at least one crosslinkable substituent or a further functional group, and unreacted sulfonyl chloride groups are subsequently hydrolyzed. The resultant aromatic sulfonamide is isolated and dissolved in an organic solvent, the solution is converted into a film, and the crosslinkable substituents in the film are then crosslinked.In specific cases, the crosslinkable substituents can be omitted.Type: GrantFiled: June 10, 1993Date of Patent: August 1, 1995Assignee: Hoechst AktiengesellschaftInventors: Freddy Helmer-Metzmann, Frank Osan, Arnold Schneller, Helmut Ritter, Konstantin Ledjeff, Roland Nolte, Ralf Thorwirth
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Patent number: 5436310Abstract: Novel aromatic poly(ether ketones) having imide, amide, ester, azo, quinoxaline, benzimidazole, benzoxazole, or benzothiazole groups, comprising, for example, a repeat unit ##STR1## are prepared by Friedel Crafts polymerization.Type: GrantFiled: June 29, 1989Date of Patent: July 25, 1995Assignee: Raychem CorporationInventors: Klaus J. Dahl, Patrick J. Horner, Heinrich C. Gors, Viktors Jansons, Richard H. Whiteley
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Patent number: 5434240Abstract: Disclosed herein are novel poly(imide-ethers) containing ortho substitution in the main chain of the polymer. These polymers are made from novel aromatic bis-carboxylic anhydrides which contain two ether groups attached to an aromatic ring in ortho positions to each other. The polymers are particularly useful for films, fibers and encapsulation, as well as thermoplastics.Type: GrantFiled: April 29, 1994Date of Patent: July 18, 1995Assignee: The University of LiverpoolInventors: Geoffrey C. Eastmond, Jerzy Paprotny
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Patent number: 5432256Abstract: The present invention provides a liquid crystal aligning film having a reduced after image and a good liquid crystal aligning property caused by a rubbing treatment of a thin film consisting of organics, and its liquid crystal display device.Type: GrantFiled: June 7, 1993Date of Patent: July 11, 1995Assignee: Chisso CorporationInventors: Yukino Abe, Minoru Nakayama, Shizuo Murata
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Patent number: 5428102Abstract: A series of polyimides based on the dianhydride of 1,4-bis(3,4-dicarboxyphenoxy)benzene (HQDEA) or on 2,2-bis[4(3-aminophenoxy)phenyl]hexafluoropropane (3-BDAF) are evolved from high molecular weight polyamic acid solutions yielding flexible free-standing films and coatings in the fully imidized form which have a dielectric constant in the range of 2.5 to 3.1 at 10 GHz.Type: GrantFiled: May 2, 1994Date of Patent: June 27, 1995Assignee: The United States of America as represented by the United States National Aeronautics and Space AdministrationInventors: Anne K. St. Clair, Terry L. St. Clair, William P. Winfree
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Patent number: 5428116Abstract: New synthesis and analysis procedures for novel crosslinked polyamines and ampholytes. Polyamines are crosslinked with tartaric acid ester, malonic acid ester, or polycarboxylic acid esters of the citric acid cycle. The resulting crosslinked polyamine may further react with other compounds such as an .alpha.,.beta.-unsaturated or .alpha.-halo unsaturated carboxylic acids to prepare new ampholyte mixtures. The resulting novel ampholytes exhibit greater heterogeneity and complexity than presently prepared ampholytes, and can be used in analytical and preparative isoelectric focusing processes.Novel ampholyte analysis process entails analyzing chemical compounds, usually ampholytes, used in isoelectric focusing processes. The ampholyte is isoelectrically focused on an immobilized pH gradient, and then immersed in a picric acid solution to cause precipitation and visualization of amphoteric species.Type: GrantFiled: March 11, 1994Date of Patent: June 27, 1995Assignee: Board of Regents, The University of Texas SystemInventors: L. Scott Rodkey, Philip R. DeShong
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Patent number: 5420233Abstract: An agent for vertical orientation treatment consisting essentially of a polyimide which contains a linear alkyl group having at least 12 carbon atoms in an amount of at least 5% by weight of the alkyl group to the total weight of the polyimide, and which, when a coating film of the polyimide is formed on a substrate, has a surface energy of not more than 38 dyn/cm.Type: GrantFiled: June 15, 1993Date of Patent: May 30, 1995Assignee: Nissan Chemical Industries Ltd.Inventors: Hideyuki Isogai, Toyohiko Abe
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Patent number: 5420232Abstract: The present invention relates to an improved process for making polyamic ester comprising reacting an aromatic diester diacid halide with the monohydrohalide salt of an aromatic diamine in the presence of a base. The polyamic ester can be imidized to form a polyimide suitable for use in electronic components.Type: GrantFiled: April 29, 1992Date of Patent: May 30, 1995Assignee: International Business Machines CorporationInventors: Daniel J. Dawson, Richard A. DiPietro
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Patent number: 5414069Abstract: An electroluminescent polymer comprises a main chain and a plurality of side chains, each of the side chains comprising an electroluminescent group and a flexible spacer connecting the electroluminescent group to the main chain, the spacers and the main chain being such that the electroluminescent groups are not conjugated with one another. The nature of the main chain and the spacer groups can be varied to enhance solubility, film-forming ability and other characteristics of the polymer, without significantly changing the electroluminescent properties of the polymer.Type: GrantFiled: February 1, 1993Date of Patent: May 9, 1995Assignee: Polaroid CorporationInventors: William J. Cumming, Russell A. Gaudiana, Richard T. Ingwall, Eric S. Kolb, Parag G. Mehta, Richard A. Minns
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Patent number: 5412066Abstract: Four phenylethynyl amine compounds--3 and 4-aminophenoxy-4'-phenylethynylbenzophenone, and 3 and 4-amino-4'-phenylethynylbenzophenone--were readily prepared and were used to endcap imide oligomers. Phenylethynyl-terminated amide acid oligomers and phenylethynyl-terminated imide oligomers with various molecular weights and compositions were prepared and characterized. These oligomers were cured at 300.degree. C. to 400.degree. C. to provide crosslinked polyimides with excellent solvent resistance, high strength and modulus and good high temperature properties. Adhesive panels, composites, films and moldings from these phenylethynyl terminated imide oligomers gave excellent mechanical performance.Type: GrantFiled: March 3, 1994Date of Patent: May 2, 1995Assignee: Ther United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Paul M. Hergenrother, Robert G. Bryant, Brian J. Jensen, Stephen J. Havens
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Patent number: 5412065Abstract: Polyimide oligomers are described which comprise the intercondensation product of a monomer mixture comprising (A) at least one aromatic bis(ether anhydride), (B) at least one phenylindane diamine, and (C) at least one end-cap monomer selected from the group consisting of monoanhydrides, acyl halides and amines, wherein each end-cap monomer (C) contains at least one crosslinkable group in the molecule and wherein the phenylindane diamine component (B) is present in the mixture in a stoichiometric excess. The monomers react in a suitable solvent under an inert atmosphere to form polyimide oligomers having a number average molecular weight of from about 1,000 to about 15,000. The polyimide oligomers of the present invention are readily processed to form polyimide matrix resins with high temperature and oxidative stability.Type: GrantFiled: April 9, 1993Date of Patent: May 2, 1995Assignee: Ciba-Geigy CorporationInventors: Michael Amone, Mark Southcott
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Patent number: 5410012Abstract: Novel poly(N-arylenebenzimidazole)s (PNABIs) are prepared by the aromatic nucleophilic displacement reaction of novel di(hydroxyphenyl-N-arylene benzimidazole) monomers with activated aromatic dihalides or activated aromatic dinitro compounds. The polymerizations are carried out in polar aprotic solvents such as N-methyl-2-pyrrolidinone or N,N-dimethylacetamide using alkali metal bases such as potassium carbonate at elevated temperatures under nitrogen. The di(hydroxyphenyl-N-arylenebenzimidazole) monomers are synthesized by reacting phenyl-4-hydroxybenzoate with bis(2-aminoanilino)arylenes in diphenylsulfone. Moderate molecular weight PNABIs of new chemical structures were prepared that exhibit a favorable combination of physical and mechanical properties. The use of the novel di(hydroxyphenyl-N-arylenebenzimidazole)s permits a more economical and easier way to prepare PNABIs than previous routes.Type: GrantFiled: March 5, 1993Date of Patent: April 25, 1995Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: John W. Connell, Paul M. Hergenrother, Joseph G. Smith, Jr.
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Patent number: 5405956Abstract: Low molecular weight cyclic oligomers of formula (I) ##STR1## in which n is an integer of 2 to 20, and each C in the oligomer is a radical of formula (II): ##STR2## and each X in the oligomer is --O--R--O-- or --S--R--S--, B and D are both carbonyl groups CO, or together represent a divalent radical of formula ##STR3## in which A.sub.1, A.sub.2, A.sub.3 A.sub.4, Ar.sub.1, Ar.sub.2 and Ar.sub.3 are selected from a variety of aromatic radicals, A.sub.1, A.sub.2, Ar.sub.3 and Ar.sub.4 also possibly being hydrogen, are useful in the production of high molecular weight, linear, polyketones, polyphthalazines and polyisoquinolines; the cyclic oligomers have low melt viscosities when heated above their softening temperatures and can be readily molded, whereafter they can be rings-open polymerized to form molded high molecular weight polymer products with excellent properties.Type: GrantFiled: March 1, 1994Date of Patent: April 11, 1995Inventors: Allan S. Hay, Kwok P. Chan
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Patent number: 5399664Abstract: The invention relates generally to polymers exhibiting second order nonlinear optical properties, and characterized by high thermal stability. Disclosed are polymers prepared by a polycondensation reaction between an aromatic dianhydride and a compound selected from the group consisting of a di(alkylamino)amine and an aromatic diamine. Most preferred are polymers that are the products of a polycondensation reaction between 1,2,4,5-benzenetetracarboxylic dianhydride and nitro(N,N-diethylamino)stilbene, wherein the polymer is imidized by further heat treatment.Type: GrantFiled: November 10, 1993Date of Patent: March 21, 1995Assignee: Arch Development CorporationInventors: Zhonghua Peng, Luping Yu
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Patent number: 5399655Abstract: 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: GrantFiled: October 29, 1993Date of Patent: March 21, 1995Assignee: E. I. du Pont de Nemours and CompanyInventor: Howard E. Simmons, III
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Patent number: 5395918Abstract: The invention describes new biphenyl dianhydrides, and new polyimides and copolyimides made from the dianhydrides. The synthesized polyimides exhibit significantly enhanced solubility when the biphenyl dianhydrides are substituted, particularly at the 2 and 2' positions on the phenyl rings.Type: GrantFiled: April 21, 1994Date of Patent: March 7, 1995Assignee: The University of AkronInventors: Frank W. Harris, Sheng-Hsien Lin
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Patent number: 5393857Abstract: A polymer scale preventive agent for use in polymerization of a monomer having an ethylenically unsaturated double bond, comprising a condensation product of (A) hydrazine and (B) a quinone compound. Where the monomer is polymerized in a polymerization vessel having, on its inner wall surface, a coating comprising the condensation product, deposition of polymer scale can be effectively prevented not only on the liquid phase part in the polymerization vessel but also near the interface between the gas phase part and the liquid phase part, so that the thus obtained polymer can provide a molded item having few fish eyes and low in initial coloration, when the polymer is molded into a sheet or the like.Type: GrantFiled: March 4, 1994Date of Patent: February 28, 1995Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Toshihide Shimizu, Mikio Watanabe
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Patent number: 5393864Abstract: A random polyimide copolymer, based on a rigid dianhydride, a rigid diamine and an additional diamine and/or dianhydride containing one or more flexibilizing linkages. Soft-baked coatings of the poly(amic acid) precursor are readily processed using conventional aqueous base developers, such as tetramethylammonium hydroxide. The polyimide and soft-baked coatings are useful as a dielectric layer In multichip module applications or as a stress buffer coating.Type: GrantFiled: April 26, 1993Date of Patent: February 28, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: John D. Summers
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Patent number: 5387657Abstract: Epoxy resins containing more than one vicinal epoxide group per molecule and at least one thiadiazole, oxadiazole or both thiadiazole and oxadiazole moiety per molecule are disclosed, as well as curable and cured compositions thereof. Certain of these epoxy resins possess enantiotropic liquid crystallinity. These enantiotropic epoxy resins are useful in preparing copolymers with high glass transition temperatures and liquid crystalline morphology, which can result in enhanced unidirectional mechanical properties. These epoxy resins are useful in coating, casting, encapsulation, electronic or structural laminate or composite, filament winding or molding applications.Type: GrantFiled: April 28, 1994Date of Patent: February 7, 1995Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Joseph A. Schomaker, Jimmy D. Earls
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Patent number: 5384390Abstract: There are disclosed flame-retardant, high temperature resistant polyimide fibers of the general formula ##STR1## wherein n is an integer larger than 1, A is a tetravalent aromatic group and R is at least one divalent aromatic group. These polyimide fibers have been heat-treated in the unstretched state and have a maximum shrinkage of 14% when heated to a temperature of 400.degree. C. These polyimide fibers are produced by initially spinning crude fibers from a solution of the appropriate polyimide in an aprotic organic solvent, preferably according to the dry-spinning method, which solution optionally contains additives. The crude fibers obtained are washed with water to remove the solvent. The washed crude fibers are dried to a moisture content of less than 5% by mass, are subjected to a heat treatment at a temperature of between 315.degree. C and 450.degree. C, are cooled and, if desired, are crimped and cut to staple fibers.Type: GrantFiled: September 23, 1991Date of Patent: January 24, 1995Assignee: Lenzing AktiengesellschaftInventors: Claus Schobesberger, Klaus Weinrotter, Herbert Griesser, Sigrid Seidl
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Patent number: 5380820Abstract: In one aspect, the present invention relates to polyimides having excellent thermal resistance and process for preparing the same comprising carrying out condensation of 4,4'-bis(3-aminophenoxy)biphenyl with pyromellitic dianhydride in the presence of a different diamine compound and optionally with a different tetracarboxylic acid dianhydride.In a second aspect, the present invention relates to a heat resistant resin composition consisting essentially of an aromatic polyetherimide and a defined polyimide.In a third aspect, the present invention relates to a polyimide resin composition comprised on a defined polyimide and a separate high-temperature engineering polymer.In a fourth aspect, the present invention relates to a resin composition comprised of a defined polyimide and an aromatic polyamideimide.Type: GrantFiled: December 7, 1993Date of Patent: January 10, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Masahiro Ohta, Masao Yoshikawa
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Patent number: 5380807Abstract: Polycondensation of, for example, squaric acid with a benzodihydropyrrole, benzodithiazole, neocuproine, terthienyl or an aromatic diamine gives a semiconductive alternating copolymer having a small band gap. It is alternatively possible to use croconic acid or 5,6-dihydroxy-5-cyclohexene-1,2,3,4-tetraone instead of squaric acid.Type: GrantFiled: January 8, 1993Date of Patent: January 10, 1995Assignee: U.S. Philips CorporationInventors: Edsko E. Havinga, Wolter Ten Hoeve, Hans Wijnberg
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Patent number: 5378799Abstract: Heat-stable polyimides and polyamideimides with modified benzhydrol structural elements and a process of preparing thereof; wherein the polyimides and polyamideimides are obtained by reacting 3,3'4,4'-benzhydroltetracarboxylic acid dimethyl ester a) with only a diamine and then cyclized to give polyimides or b) with a diamine and with trimellitic, phthalic-or isophthalic acid (or the anhydrides, acid chlorides, anhydride chlorides or esters) and is then cyclized to give polyamideimides.Type: GrantFiled: September 13, 1993Date of Patent: January 3, 1995Assignee: Chemie Linz GmbHInventors: Gerhard Greber, deceased, Heinrich Gruber, Marcel Sychra
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Patent number: 5374708Abstract: Polyimide filaments and polyimide films having great strength, high elastic modulus and high crystallinity and comprising a novel polyimide which can be melt-processed without impairing high crystallinity and which essentially consists of recurring structural units represented by the formula (I): ##STR1## more than 85 mol % the polyimide consists of recurring structural units of the formula (II): ##STR2## and from 0.5 to 15 mol % of the polyimide consists of recurring structural units represented by the formula (III), the formula (II) exclusive, the formula (IV) and/or the formula (V).Type: GrantFiled: August 8, 1991Date of Patent: December 20, 1994Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Shoji Tamai, Masahiro Ohta, Akihiro Yamaguchi, Masumi Saruwatari
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Patent number: 5371168Abstract: Amorphous polyimide powder which has recurring structural units of the formula (I): ##STR1## as a fundamental skeleton, is blocked at the polymer chain end with dicarboxylic anhydride represented by the formula (II) ##STR2## wherein Z is a divalent radical having from 6 to 27 carbon atoms and selected from the group consisting of a monoaromatic radical, condensed polyaromatic radical and noncondensed aromatic radical connected to each other with a direct bond or a bridge member, and essentially has no reactive radical at the polymer chain end, preparation process of the amorphous polyimide powder, heat-resistant adhesive comprising the polyimide, and bonding method using the adhesive.Type: GrantFiled: June 5, 1992Date of Patent: December 6, 1994Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Wataru Yamashita, Shoji Tamai, Akihiro Yamaguchi
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Patent number: 5362837Abstract: Macrocyclic polyetherimide oligomer compositions are prepared by a displacement reaction at a temperature in the range of about 200.degree.-225.degree. C. between at least one fluorinated aromatic phthalimide and at least one phenolic trialkylsilyl ether compound. Preferably, a bis-fluoroimide and a bis-trialkylsilyl ether of a dihydroxyaromatic compound such as resorcinol are employed. The reaction is conducted by maintaining reagents A and B in high dilution in a dipolar aprotic organic liquid such as N-methylpyrrolidone, and in the presence of a catalytic amount of at least one substantially soluble fluoride. Preferably, a mixture of reagents A and B is added to solvent containing the catalyst.Type: GrantFiled: July 26, 1993Date of Patent: November 8, 1994Assignee: General Electric CompanyInventors: Tohru Takekoshi, Jane M. Terry
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Patent number: 5357033Abstract: Film forming aromatic organic polymers are provided having a dielectric constant greater than 3 resulting from the polymerization of aromatic organic monomers having orientable organic dipolar groups with a net dipole moment of at least 0.5 Debye. Among the aromatic organic polymers are included polyimides and polyetherimides having repeat main chain groups with orientable organic dipolar groups with non-symmetrically positioned polar radicals, such as fluoro and nitrile.Type: GrantFiled: April 1, 1993Date of Patent: October 18, 1994Assignee: General Electric CompanyInventors: John T. Bendler, Tohru Takekoshi, Clive W. Reed
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Patent number: 5357032Abstract: A diamine compound of the general formula ##STR1## wherein the arrows denote isomerism, R.sub.1 is a divalent aromatic group selected from the group consisting of ##STR2## R.sub.2 is a tetravalent aromatic group selected from the group consisting of ##STR3## and R.sub.4 is a monovalent aliphatic group selected from the group consisting of ethyl and isopropyl; and, a process for preparing same.Type: GrantFiled: August 17, 1992Date of Patent: October 18, 1994Assignee: Korea Research Institute of Chemical TechnologyInventors: Suh Bong Rhee, Ji Y. Chang, Bong S. Moon, Ji-Woong Park
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Patent number: 5354839Abstract: A polyimide comprising a requisite structural unit having one or more recurring structural units of the formula: ##STR1## such as the structural units of the formula ##STR2## The polyimide can have an extremely low dielectric constant and is colorless, transparent and excellent in processability and heat resistance, and also provides an aromatic diamine which is useful as a raw material monomer of the polyimide or a raw material of other various engineering plastics.Type: GrantFiled: March 31, 1993Date of Patent: October 11, 1994Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Wataru Yamashita, Yoshihiro Sakata, Toshiyuki Kataoka, Yuichi Okawa, Hideaki Oikawa, Tadashi Asanuma, Mitsunori Matsuo, Tsutomu Ishida, Keizaburo Yamaguchi, Akihiro Yamaguchi
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Patent number: 5346982Abstract: A polyimide-based heat-resistant adhesive having excellent peel strength and heat resistance comprising polyimide composed of 10 to 99% by mole of structural units having the formula (1) and 1 to 90% by mole of structural units having the formula (2) or comprising polyamic acid precursor which corresponds to the polyimide.Type: GrantFiled: June 7, 1993Date of Patent: September 13, 1994Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Shoji Tamai, Katsuaki Iiyama, Akihiro Yamaguchi
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Patent number: 5344916Abstract: A negative birefringent film, useful in liquid crystal displays, and a method for controlling the negative birefringence of a polyimide film is disclosed which allows the matching of an application to a targeted amount of birefringence by controlling the degree of in-plane orientation of the polyimide by the selection of functional groups within both the diamine and dianhydride segments of the polyimide which affect the polyimide backbone chain rigidity, linearity, and symmetry. The higher the rigidity, linearity and symmetry of the polyimide backbone, the larger the value of the negative birefringence of the polyimide film.Type: GrantFiled: June 4, 1993Date of Patent: September 6, 1994Assignee: The University of AkronInventors: Frank W. Harris, Stephen Z. D. Cheng
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Patent number: 5340914Abstract: A method and apparatus are disclosed for conducting a physical process and a chemical reaction by exposing a material containing a volatile substance to microwave radiation where the morphology of said material will change when exposed to such radiation. The power of said radiation is adjusted over time as the morphology of the material changes to maximize the effect of the radiation in order to produce a product in a minimum amount of time that is substantially free of said volatile substance.The method and apparatus can also be used to conduct such a process or reaction with materials that do not contain a volatile material.In one embodiment a method and apparatus are disclosed for manufacturing a polyimide from a precursor in a solvent by exposing the precursor to microwave radiation in a tuneable microwave resonant cavity that is tuned during imidization to achieve critical coupling of the system. Microwave power is controlled to remove the solvent and obtain the desired level of reaction.Type: GrantFiled: June 16, 1993Date of Patent: August 23, 1994Assignee: International Business Machines CorporationInventors: Jerome J. Cuomo, Jeffrey D. Gelorme, Michael Hatzakis, Jr., David A. Lewis, Jane M. Shaw, Stanley J. Whitehair
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Patent number: 5340904Abstract: A compound or polymer having a bis(phenoxy)naphthalene structure, a high molecular weight, and very good mechanical performance and heat-resistivity is provided. The polymer can be polyamides, polyimides or poly(amide-imide)s and can have a basic structure of ##STR1## wherein R1 is a naphthalene ring.Type: GrantFiled: December 29, 1992Date of Patent: August 23, 1994Assignee: National Science CouncilInventors: Chin-Ping Yang, Wen-Tung Chen
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Patent number: 5338826Abstract: A structure which is effective as an electrical insulator or as a transmitter-receiver of electromagnetic energy is prepared by providing a suitable substrate and covering the substrate with an adhering layer of a low dielectric, high temperature, linear aromatic polyimide.Type: GrantFiled: September 28, 1992Date of Patent: August 16, 1994Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministationInventors: Anne K. St. Clair, Terry L. St. Clair, William P. Winfree
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Patent number: 5334697Abstract: A polyimide gas separation membrane containing repeating units derived from 9,9-disubstituted xanthene dianhydride is disclosed.Type: GrantFiled: October 4, 1993Date of Patent: August 2, 1994Assignee: L'Air Liquide, S.A.Inventor: John W. Simmons
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Patent number: 5332799Abstract: In solutions of polyimide-forming starting materials, containing diamines and tetracarboxylic diesters, at least 2 mol % of the ester groups in the tetracarboxylic diesters are derived from alcohols of the general formulaHO--Z--O--X IorHO--Z--X IIwhere Z is a straight-chain or branched aliphatic radical of from 1 to 15 carbon atoms which can be interrupted by from 1 to 4 ether groups --O-- and X is an aromatic radical of from 5 to 20 carbon atoms which can also contain nitrogen, oxygen or sulfur as hetero atoms in the aromatic ring system, excepting benzyl alcohol as compound of the formula II in the case of the use of diamines having a basicity constant of less than or equal to 10.sup.-11.Type: GrantFiled: November 2, 1992Date of Patent: July 26, 1994Assignee: BASF Lacke+Farben AktiengesellschaftInventors: Rainer Blum, Hans J. Heller, Klaus Lienert
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Patent number: 5328979Abstract: Copolyimide compositions and methods for their preparation which are melt-processible at relative low pressures, i.e. less than 1000 psi, and are suited for laminating and molding, are described. The invention additionally encompasses copolyimide precursors, reinforced polyimide composites and laminates made from said polyimides where the composite is reinforced by fibrous materials. This is achieved by reacting at least one aromatic dianhydride where each anhydride group is located on an aromatic ring with the carbonyl units in an ortho orientation relative to one another, with at least one diamine which is capable of a transmidization reaction upon incorporation into the polyimide backbone, and with at least one other diamine which is not capable of undergoing such reaction, the diamine which is capable of undergoing the transimidization reaction being present in an amount of from about 1-50 mole percent in relation to the diamine that is not susceptable to transimidization.Type: GrantFiled: November 16, 1992Date of Patent: July 12, 1994Assignee: The University of AkronInventors: Frank Harris, Patricia A. Gabori
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Patent number: 5324813Abstract: Low dielectric constant polyimides formed from an optionally fluorinated dianhydride and a fluorinated diamine are described. The fluorine containing constituents are sterically disposed so that the dipole moment of the constituents tend to cancel out. Since fluorine containing diamines are generally nonreactive, to achieve a polyimide of high enough molecular weight to be practically useful, a method of fabrication of a high molecular weight polymer from monomers of low reactivity is provided. The monomers, such as a diamine and dianhydride are provided in a solution within which a low molecular weight polyamic acid is formed. The solution is dried. The polyamic acid used is cured to a low molecular weight polyimide. The polyimide is redisolved, redryed and recured enough times to build up the molecular weight to a useful level. The method is applicable to fabricating other polymers of high molecular weight, such as polyamides, polyesters and polyurethanes.Type: GrantFiled: July 22, 1992Date of Patent: June 28, 1994Assignee: International Business Machines CorporationInventors: Gareth G. Hougham, Jane M. Shaw, Alfred Viehbeck
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Patent number: RE34820Abstract: Sizing for carbon fibers with uncapped or capped linear polyamideimides.The uncapped linear polyamideimides useful as carbon fiber sizings generally contain repeating units having the general formula: ##STR1## Wherein R.sub.2 =a trivalent organic radical and generally benzenetriyl;R.sub.3 =a divalent organic radical; andn=an integer sufficiently large to provide a strong, tough coating.Useful capped, linear polyamideimide oligomers may be formed by including end caps with an unsaturated functionality (Y) containing a residue selected from the group consisting of: ##STR2## wherein R.sub.1 =lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl, halogen, or mixtures thereof;j=0, 1 or 2;i=1 or 2;G=--CH.sub.2 --, --O--, --S--, --SO.sub.2 --, --SO--, --CO--, --CHR--, or --CR.sub.2 --;T=methallyl or allyl;Me=methyl; andR=hydrogen, lower alkyl, or phenyl.Prepregs and composites having carbon fibers sized with such polyamideimides are also described.Type: GrantFiled: November 15, 1993Date of Patent: January 3, 1995Assignee: The Boeing CompanyInventors: Hyman R. Lubowitz, Clyde H. Sheppard, Ronald R. Stephenson