Carboxylic Acid Contains At Least Four Carboxylic Acid Groups Or Is A Derivative Of A Carboxylic Acid Containing At Least Four Carboxylic Groups Patents (Class 528/353)
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Patent number: 5789524Abstract: A process for producing a polyimide composition by reacting at least one polyamic acid or at least one polyamic ester or a mixture of at least one polyamic acid and at least one polyamic ester with a selected phosphoramide in the presence of at least one base catalyst to from a polyimide composition.Type: GrantFiled: April 15, 1997Date of Patent: August 4, 1998Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Steve L. C. Hsu, Ahmad Naiini, William D. Weber, Andrew J. Blakeney
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Patent number: 5789523Abstract: Polyimide compositions can be substantially improved by incorporating in the composition an inorganic, low hardness, thermally stable, sheet silicate, such as muscovite mica, talc, and kaolinite, which results in improved wear resistance and reduced coefficient of friction.Type: GrantFiled: July 9, 1996Date of Patent: August 4, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Daniel Eugene George, Joy Sawyer Bloom, Thomas Paul Feist
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Patent number: 5783656Abstract: There are provided a polyamic acid obtainable by reacting a diamine compound of the formula (1) ##STR1## wherein R.sup.1 is an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms or a halogen atom, each of X and Y is independently a divalent linking group,with a tetracarboxylic acid dianhydride; a polyimide obtainable by dehydrating and ring-closing the above polyamic acid; and a liquid crystal aligning agent containing the above polyamic acid and/or the above polyimide.Type: GrantFiled: January 31, 1997Date of Patent: July 21, 1998Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Masayuki Kimura, Tsukasa Toyoshima, Keiichi Yamamoto, Kengo Wakabayashi, Yasuo Matsuki, Kyouyu Yasuda
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Patent number: 5780199Abstract: Copolyamic acid is obtained from tetracarboxylic acid dianhydride, diamine and a fluorinated diamine and/or fluorinated tetracarboxylic acid dianhydride; and optionally ester or amine salt derivative thereof to obtain radiation sensitive polymer; and low optical high thermally stable polyimide from curing the above polyamic acid and/or derivative thereof.Type: GrantFiled: May 16, 1995Date of Patent: July 14, 1998Assignee: International Business Machines CorporationInventors: Marie Angelopoulos, Jeffrey Donald Gelorme, Jeffrey William Labadie, David Andrew Lewis, Sally Ann Swanson, Nancy Carolyn Labianca
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Patent number: 5777068Abstract: Provided are photosensitive resin compositions comprising a polyamic compound having, at each terminal thereof, a specific actinic ray-sensitive functional group which has substituent groups each having a photopolymerizable carbon-carbon double bond, a photosensitive auxiliary having a photopolymerizable functional group and a solvent. The photosensitive resin compositions of the invention are excellent in resist properties such as sensitivity and good in storage stability and can provide a film small in residual stress.Type: GrantFiled: September 12, 1995Date of Patent: July 7, 1998Assignees: Nippon Zeon Co., Ltd., Fujitsu LimitedInventors: Akira Tanaka, Satoshi Tazaki, Kei Sakamoto, Yasuhiro Yoneda, Kishio Yokouchi, Daisuke Mizutani, Yoshikatsu Ishizuki
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Patent number: 5773559Abstract: The present invention relates to a process of producing a polyimide-type copolymer, to a thin layer forming agent, to a liquid crystal alignment layer and to processes of producing thin layer formation agents and liquid crystal alignment layers. More specifically, this invention relates to a polyamic acid block copolymer, a polyimide block copolymer, a polyimide-polyamic acid block copolymer, a thin layer forming agent comprised of a polyimide-type block copolymer, and a liquid crystal alignment layer comprised of a polyimide-type block copolymer and processes of their production.Type: GrantFiled: January 31, 1996Date of Patent: June 30, 1998Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Tsuyoshi Miyamoto, Masayuki Kimura, Kazuhiro Eguchi, Yasuo Matsuki
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Patent number: 5773553Abstract: Disclosed is a process which comprises reacting a polyimide precursor with borane. Also disclosed is a thermal ink jet printhead containing a layer comprising the product of this reaction.Type: GrantFiled: June 13, 1996Date of Patent: June 30, 1998Assignee: Xerox CorporationInventors: Timothy J. Fuller, Ram S. Narang
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Patent number: 5773509Abstract: A heat resistant resin composition comprising, as the main components,(A) 100 parts by weight of an organic solvent-soluble polyimide resin having a glass transition temperature of 350.degree. C. or less,(B) 5 to 100 parts by weight of an epoxy compound having at least two epoxy groups in one molecule, and(C) 0.1 to 20 parts by weight of a compound having an active hydrogen group which can react with the epoxy compound (B),a heat resistant film adhesive comprising, as the main components, the above components (A), (B) and (C), and a process for producing a heat resistant film adhesive by casting a solution of the above heat resistant resin composition on one side or both sides of a support.Type: GrantFiled: March 7, 1995Date of Patent: June 30, 1998Assignee: Sumitomo Bakelite Company LimitedInventors: Tatsuhiro Yoshida, Keizo Takahama, Syusaku Okamyo
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Patent number: 5773561Abstract: The present invention relates generally to a new adhesive comprising a vinyl containing siloxane-containing polyimide for use in TSM capping of electronic package assemblies with adhesive capability of providing a seal band width of less than 4mm and even less than 2mm, solubility in non-toxic and environmentally safe solvents and durable adhesive properties and to a method for making the polyimides, a method for using the polyimides to make electronic packages and electronic packages made using the adhesive. The preferred vinyl-containing siloxane containing polyimide is a block type polymer containing blocks of a dianhydride-aromatic diamine oligomeric reaction product joined by non-vinyl/vinyl containing siloxane diamine forming links.Type: GrantFiled: August 2, 1996Date of Patent: June 30, 1998Assignee: International Business Machines CorporationInventors: Krishna Gandhi Sachdev, Michael Berger, Patrick A. Coico, Frank L. Pompeo
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Patent number: 5770676Abstract: In the process of the present invention, a non-polar, aprotic solvent is removed from an oligomer/polymer solution by freeze-drying in order to produce IPNs and semi-IPNs. By thermally quenching the solution to a solid in a short length of time, the size of the minor constituent-rich regions is greatly reduced as they are excluded along with the major constituent from the regions of crystallizing solvent. The use of this process sequence of controlling phase morphology provides IPNs and semi-IPNs with improved fracture toughness, microcracking resistance, and other physical-mechanical properties as compared to IPNs and semi-IPNs formed when the solvent is evaporated rather than sublimed.Type: GrantFiled: April 10, 1996Date of Patent: June 23, 1998Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Ruth H. Pater, Marion G. Hansen
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Patent number: 5759442Abstract: A polyimide alignment film based on 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride and ortho-substituted aromatic diamines, such as 2,3,5,6-tetramethyl-p-phenylene diamine, 2,4,6-trimethyl-m-phenylene diamine and 1,5-diaminonaphthalene, providing high voltage holding ratio and high tilt angle when used in active matrix liquid crystal displays.Type: GrantFiled: March 7, 1997Date of Patent: June 2, 1998Assignees: E. I. du Pont de Nemours and Company, Merck Patent GmbHInventors: Brian Carl Auman, Edgar Bohm, Bernd Fiebranz
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Patent number: 5760168Abstract: 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: GrantFiled: October 21, 1996Date of Patent: June 2, 1998Assignee: The United States of America as represented by the Administrator of the National Aeuonautics and Space AdministrationInventors: Paul M. Hergenrother, Joesph G. Smith, Jr.
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Patent number: 5756649Abstract: 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: GrantFiled: January 28, 1997Date of Patent: May 26, 1998Assignees: Japan Synthetic Rubber Co., Ltd., Sharp CorporationInventors: Shigeaki Mizushima, Noriko Watanabe, Hiroko Iwagoe, Seiji Makino, Sigeo Kawamura, Yusuke Tsuda, Nobuo Bessho
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Patent number: 5756648Abstract: Photosensitive polyimides (Ps-PIM) materials have been synthesized that belong to three families of Ps-PIM materials. Through the use of precursors, various catalytic compositions with differing photosensitivities are provided. The results are Ps-PIM materials having increased photosensitivities at wavelengths longer than approximately 330 to 350 nm and an associated catalytic system that is insensitive to oxygen. A variety of applications, including use in holographic systems, are improved by the present invention.Type: GrantFiled: October 25, 1995Date of Patent: May 26, 1998Assignee: Tamarack Storage Devices, Inc.Inventor: Chung J. Lee
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Patent number: 5756650Abstract: A polyimide precursor composition, which comprises, a polyamic acid having a repeating unit represented by the following general formula (PA), and at least one kinds of cure accelerator selected from the group consisting of a substituted or unsubstituted nitrogen-containing heterocyclic compound exhibiting an acid dissociation index "pKa" of a proton complex ranging from 0 to 8 in an aqueous solution thereof, or an N-oxide compound of said nitrogen-containing heterocyclic compound (AC1), a substituted or unsubstituted amino acid compound (AC2), and an aromatic hydrocarbon compound or an aromatic heterocyclic compound having a molecular weight of 1,000 or less and two or more hydroxyl groups (AC3): ##STR1## wherein .phi. is a quadrivalent organic group, .phi. is a bivalent organic group, R is a substituted or unsubstituted hydrocarbon group, organosilicic group or hydrogen atom.Type: GrantFiled: March 13, 1997Date of Patent: May 26, 1998Assignee: Kabushiki Kaisha ToshibaInventors: Yoshiaki Kawamonzen, Masayuki Oba, Satoshi Mikoshiba, Shigeru Matake
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Patent number: 5750633Abstract: A dope for cast formation comprising a fluorine including polyimide resin and an organic solvent (P) as main components. The fluorine including polyimide resin has at least one --CF.sub.3 group in the repeating molecular unit. The organic solvent (P) is present during the resin polymerization of the fluorine including polyimide resin. The organic solvent (P) is diethylene glycol dimethyl ether.Type: GrantFiled: October 24, 1995Date of Patent: May 12, 1998Assignee: Nitto Denko CorporationInventors: Tomomi Ohara, Hisao Hachisuka
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Patent number: 5750636Abstract: This invention provides a process wherein a stable solution of polycarbodiimide with a number-average molecular-weight of 5,000 to 60,000 can be very easily prepared by using an organic diisocyanate (e.g., 2,4-tolylene diisocyanate or 2,6-tolylene diisocyanate) as starting material, a cyclic phosphine oxide as catalyst and a chlorinated aromatic compound as solvent and by controlling certain reaction conditions within the reaction temperature range of 110.degree. to 150.degree. C.Type: GrantFiled: June 4, 1996Date of Patent: May 12, 1998Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Yasuyoshi Komoto, Yasuyuki Takiguchi, Ken Yahata, Akira Hayashida, Minoru Takamizawa
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Patent number: 5750637Abstract: This invention provides a process for the preparation of a polycarbodiimide solution wherein the polycarbodiimide is synthesized by heating an organic diisocyanate (e.g., 2,4-tolylene diisocyanate or 2,6-tolylene diisocyanate) in the presence of a carbodiimidation catlayst characterized in that a non-chlorinated aromatic hydrocarbon is used as the solvent and the resulting polycarbodiimide has a number average molecular weight from about 3,000 to about 10,000; wherein the synthesis is performed in the temperature range of from about 100.degree. to about 120.degree. C.Type: GrantFiled: June 4, 1996Date of Patent: May 12, 1998Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Yasuyuki Takiguchi, Ken Yahata, Yasuyoshi Komoto, Akira Hayashida, Minoru Takamizawa
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Patent number: 5750641Abstract: 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: GrantFiled: May 23, 1996Date of Patent: May 12, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Stephen A. Ezzell, Hassan Sahouani, Ernest L. Thurber
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Patent number: 5744575Abstract: An aromatic polyimide having a recurring unit of the formula (I): ##STR1## wherein Ar is a divalent aromatic group having one or two benzene rings which has a sulfonate group of --SO.sub.3 H, --SO.sub.3 M, and --SO.sub.3 N(L).sub.4 on the ring, wherein M is an alkali metal and L is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, is favorably employed in the form of a semipermeable film for gas separation.Type: GrantFiled: June 6, 1996Date of Patent: April 28, 1998Assignee: Ube Industries, Ltd.Inventors: Shunsuke Nakanishi, Kenji Ito, Yoshihiro Kusuki
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Patent number: 5741585Abstract: Polyimide precursor solutions comprise an organic liquid and the reaction product of an aromatic dianhydride and an aromatic diaminobenzoxazole capped, on at least one terminal end, with a bifunctional chain extender. The bifunctional chain extender has one functional group reactive with the amine of the aromatic diaminobenzoxazole or the anhydride of the aromatic dianhydride and another functional group which does not form amic acid linkages, but which is capable of further reaction to increase the molecular weight of the polyimide precursor under conditions other than those used to react the aromatic diamine and aromatic dianhydride to form the polyimide precursor. These polyimide precursors can be converted into polyimidebenzoxazole polymers.Type: GrantFiled: April 24, 1995Date of Patent: April 21, 1998Assignee: The Dow Chemical CompanyInventors: William J. Harris, Wen-Fang Hwang
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Patent number: 5741883Abstract: Tough, soluble, aromatic, thermoplastic copolyimides were prepared by reacting 4,4'-oxydiphthalic anhydride, 3,4,3',4'-biphenyltetracarboxylic dianhydride and 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: GrantFiled: December 16, 1994Date of Patent: April 21, 1998Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventor: Robert G. Bryant
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Patent number: 5739263Abstract: 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: GrantFiled: January 28, 1994Date of Patent: April 14, 1998Assignee: Sumitomo Bakelite Company LimitedInventors: Tatsuhiro Yoshida, Yoshitaka Okugawa, Toshio Suzuki, Toshiro Takeda, Yushi Sakamoto, Takuya Tochimoto
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Patent number: 5736592Abstract: A process for intramolecularly condensing a polyamic acid composition containing an NLO compound to form a polyimide host matrix composition containing as a guest the NLO compound, which process includes the step of uniformly heating the polyamic acid composition, in the absence of a solvent or diluent, to a temperature at which the intramolecular condensation will occur without thermal degradation of the NLO compound, so that the temperature differential within the polyamic acid is below that which will produce localized thermal degradation temperatures, until the intramolecular condensation of the polyamic acid composition to the polyimide host matrix composition is substantially complete. Polyimide host matrix compositions containing guest NLO compounds prepared by the inventive process are also disclosed, wherein the NLO compounds have external field-induced molecular alignments.Type: GrantFiled: February 15, 1995Date of Patent: April 7, 1998Assignee: Enichem S.p.A.Inventors: Mark Thomas DeMeuse, Diana Marie Applegate, Kwan-Yue Alex Jen, John Thomas Kenney
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Patent number: 5734008Abstract: 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: GrantFiled: October 23, 1995Date of Patent: March 31, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Mika Shirasaki, Youichi Ueda, Mitsuhiro Shibata
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Patent number: 5731404Abstract: 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: GrantFiled: November 1, 1995Date of Patent: March 24, 1998Assignees: E. I. du Pont de Nemours and Company, Merck Patent GmbHInventors: Brian Carl Auman, Edgar Bohm
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Patent number: 5731405Abstract: 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: GrantFiled: March 29, 1996Date of Patent: March 24, 1998Assignee: Alliant Techsystems Inc.Inventors: Wayne M. Gibbons, Paul J. Shannon, Shao-Tang Sun
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Patent number: 5723571Abstract: 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: GrantFiled: August 29, 1996Date of Patent: March 3, 1998Assignee: Tomoegawa Paper Co., Ltd.Inventors: Osamu Oka, Takeshi Nishigaya
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Patent number: 5721335Abstract: Rigid-rod and segmented rigid-rod polymers, methods for preparing the polymers and useful articles incorporating the polymers are provided. The polymers incorporate rigid-rod backbones with pendant solubilizing groups attached thereto for rendering the polymers soluble.Type: GrantFiled: June 2, 1995Date of Patent: February 24, 1998Assignee: Maxdem IncorporatedInventors: Matthew Louis Marrocco, III, Robert R. Gagne, Mark Steven Trimmer
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Patent number: 5719253Abstract: This invention provides a poly(amic acid) solution which does not contain aprotic polar solvents such as DMF, NMP, DMAc, DMSO, as well as a polyimide film obtained therefrom having appropriate flexibility and a small coefficient of linear thermal expansion and a coated material in which the polyimide film is formed on a substrate.More particularly, it provides a poly(amic acid) solution which has an aromatic poly(amic acid) and a tertiary amine as the solute and a water soluble alcohol compound and/or a water soluble ether compound as the solvent and contains substantially no aprotic polar solvent, as well as a polyimide film obtained from the poly(amic acid) solution and a coated material obtained by forming the film on a substrate.Type: GrantFiled: October 5, 1995Date of Patent: February 17, 1998Assignee: Unitika Ltd.Inventors: Yoshiaki Echigo, Shoji Okamoto, Hiroshi Yamada, Isao Tomioka, Yoshiaki Iwaya
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Patent number: 5714572Abstract: The present invention provides a polyimide resin composition comprising:(a) a polyamide resin comprising a repeating unit represented by the general formula (1): ##STR1## wherein X represents a tetravalent organic group represented by the formula (2): ##STR2## Y represents a divalent organic group comprising a divalent siloxane residual group represented by the formula (3): ##STR3## wherein m is an integer of 60 to 120; and a divalent aromatic group represented by the formula (4): ##STR4## wherein R.sup.1 represents a hydrogen atom or a fluorine atom; and (B) cyclohexanone. From this composition, polyimide resin films can be obtained by heating at a lower temperature for a short time, and the films obtained show good adhesion under moisture-resistant conditions.Type: GrantFiled: October 23, 1996Date of Patent: February 3, 1998Assignee: Shin-Etsu Chemical Co., Ltd.Inventor: Hideto Kato
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Patent number: 5714566Abstract: 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: GrantFiled: June 5, 1995Date of Patent: February 3, 1998Assignee: The Boeing CompanyInventors: Hyman R. Lubowtiz, Clyde H. Sheppard
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Patent number: 5710241Abstract: The present invention relates to monoanhydride monomer compounds, methods of making such compounds and reaction products of the monoanhydride-diacid compounds with other monomers. The inventive monomer compounds exhibit selective reactivity, that is, the dianhydride locus is substantially more reactive towards amines than the diacid locus making it possible to sequentially synthesize a new class of materials suitable for membranes, catalytic substrates or any speciality material required for advanced applications.Type: GrantFiled: March 2, 1994Date of Patent: January 20, 1998Assignee: Hoechst Celanese Corp.Inventors: Michael Haubs, Paul Foley, Dominick L. Cangiano
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Patent number: 5708127Abstract: The invention relates to a PMR type resin which comprises a mixture of:(a) nadic acid of Formula (Ia) or a derivative thereof ##STR1## (b) a diaminobisimide of Formula (Ib) ##STR2## (c) an aromatic tetracarboxylic acid of Formula (Ic) or a derivative thereof ##STR3## the components (a), (b) and (c) being present in the approximate molar proportions of 2:n:n-1 respectively.Type: GrantFiled: July 21, 1995Date of Patent: January 13, 1998Assignee: Commonwealth Scientific and Industrial Research OrganisationInventors: Jonathan Howard Hodgkin, Robert Eibl
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Patent number: 5708128Abstract: 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: GrantFiled: June 24, 1996Date of Patent: January 13, 1998Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Hideaki Oikawa, Shoji Tamai, Masahiro Ohta, Akihiro Yamaguchi
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Patent number: 5708122Abstract: 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: GrantFiled: April 19, 1996Date of Patent: January 13, 1998Assignee: E. I. Du Pont de Nemours and CompanyInventor: Robert Ralph Luise
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Patent number: 5698135Abstract: A liquid crystal-aligning agent comprising at least one of a polyamic acid obtained by reacting (A) a tetracarboxylic acid dianhydride consisting of 70 to 98 mole % of a dianhydride of a tetracarboxylic acid such as ##STR1## or the like, and 2 to 30 mole % of a dianhydride of a cyclobutanetetracarboxylic acid, and (B) a diamine compound, and a polymer obtained by imidizing the polyamic acid.Type: GrantFiled: December 7, 1995Date of Patent: December 16, 1997Assignee: Japan Synthetic Rubber Co., Ltd., a Japanese CorporationInventors: Michinori Nishikawa, Shigeo Kawamura, Yasuo Matsuki, Kyouyu Yasuda, Tsuyoshi Miyamoto
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Patent number: 5696235Abstract: 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: GrantFiled: May 17, 1996Date of Patent: December 9, 1997Assignee: Tomoegawa Paper Co., Ltd.Inventors: Osamu Oka, Takeshi Hashimoto, Takeshi Nishigaya
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Patent number: 5693745Abstract: 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: GrantFiled: February 8, 1996Date of Patent: December 2, 1997Assignee: Industrial Technology Research InstituteInventors: Lee-Ching Kuo, Jinn-Shing King, Wen-Yueh Hsu, Yu-Tai Tsai
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Patent number: 5688906Abstract: 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: GrantFiled: August 7, 1995Date of Patent: November 18, 1997Assignee: Enichem S.p.A.Inventors: Kwan-Yue Alex Jen, Kevin Joel Drost
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Patent number: 5686558Abstract: 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: GrantFiled: March 29, 1995Date of Patent: November 11, 1997Assignee: Toray Industries, Inc.Inventors: Kazuo Kitamura, Satoshi Okawa
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Patent number: 5686559Abstract: 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: GrantFiled: October 30, 1995Date of Patent: November 11, 1997Assignee: Korea Research Institute of Chemical TechnologyInventors: Suh Bong Rhee, Myong Hoon Lee, Ji Woong Park
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Patent number: 5686525Abstract: A polyimide precursor composition which is produced by (i) providing a polyamide acid solution obtained by reacting an aromatic tetracarboxylic acid component and a diamine component in the presence of an oxygen-containing solvent and (ii) subjecting said polyamide acid solution to heat treatment. The polyimide precursor composition exhibits a desirable apparent viscosity and a desirable thixotropic property and it excels in film forming ability, and because of this, it enables the formation a high quality relief pattern film with no defect and which excels in form retention by way of the screen printing.Type: GrantFiled: March 14, 1996Date of Patent: November 11, 1997Assignee: Central Glass Company, Ltd.Inventors: Masamichi Maruta, Hidehisa Nanai, Yoshihiro Moroi, Hiroshi Takahashi, Seiji Hasegawa
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Patent number: 5677418Abstract: A silver organic complex, such as silver acetate, is solubilized in a polyamic acid resin or soluble polyimide solution using a suitable solvent such as hexafluoroacetyl acetone. The mixture is stable and can be applied to both flat and contoured surfaces. Application can be performed by casting, dip-coating, spraying, or other suitable techniques. In addition, the mixture can be cast or extruded as a polyimide film which is not applied to an underlying substrate. Upon curing, a flexible silver coated polyimide film is produced.Type: GrantFiled: June 14, 1995Date of Patent: October 14, 1997Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: David W. Thompson, Maggie L. Caplan, Anne K. St. Clair
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Patent number: 5674575Abstract: The present invention provides a liquid crystal aligning film containing as the principal constituent a polyimide resin, which comprises two or more diamines, and having a stripping load of 4.0 gf or more measured by particular conditions, and a liquid crystal display device using it. The liquid crystal aligning film has excellent resistance to liquid crystals, and does not have partial disorder of liquid crystal alignment caused by many scratches made by rubbing treatment.Type: GrantFiled: April 18, 1995Date of Patent: October 7, 1997Assignee: Chisso CorporationInventors: Yukino Abe, Shizuo Murata
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Patent number: 5670609Abstract: 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: GrantFiled: August 8, 1995Date of Patent: September 23, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventors: Brian Carl Auman, Edgar Bohm
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Patent number: 5670603Abstract: 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: GrantFiled: March 8, 1993Date of Patent: September 23, 1997Assignee: AlliedSignal Inc.Inventors: Chengjiu Wu, Jianhui Shan, Ajay Nahata
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Patent number: 5668248Abstract: A photosensitive resin composition comprising, as its main ingredient, a poly(amic acid) resin constituted of a diamino compound represented by formula: ##STR1## and optionally used other diamino compound and a tetracarboxylic acid dianhydride as its constituent monomers and/or a poly(amic acid) ester resin obtained by esterifying said poly(amic acid) resin and/or a polyimide resin obtained by a dehydrating or alcohol-eliminating ring-closure reaction of said poly(amic acid) resin or poly(amic acid) ester resin has an excellent developability and a high film strength and can form a relief patter of low thermal expansion.Type: GrantFiled: August 22, 1995Date of Patent: September 16, 1997Assignee: Hitachi Chemical Co., Ltd.Inventors: Hideo Hagiwara, Makoto Kaji, Hiroshi Nishizawa, Kenji Suzuki, Yasunori Kojima
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Patent number: 5667899Abstract: An electrically conductive bonding film useful in bonding an IC or LSI with a lead frame. The film comprises (A) a polyimide resin obtained by reacting a tetracarboxylic dianhydride component, in which the content of a tetracarboxylic dianhydride represented by the following formula (I): ##STR1## wherein n stands for an integer of 2-20 amounts to at least 70 mole %, with a diamine; and (B) an electrically conductive filler. Optionally, the film may further comprises a thermosetting resin or an imide compound having at least two thermally-crosslinking imido groups per molecule.Type: GrantFiled: June 7, 1995Date of Patent: September 16, 1997Assignee: Hitachi Chemical Co. Ltd.Inventors: Masami Yusa, Shinji Takeda, Takashi Masuko, Yasuo Miyadera, Mitsuo Yamazaki
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Patent number: 5668245Abstract: A new class of polymers include repeating units comprising one or more arylene units substituted with heterocyclic side groups. The heterocyclic substituted arylene repeat units have the general structural formula: ##STR1## wherein Het is a heterocyclic group, R is an optional substituent, x is 1 or 2, and y is less than or equal to 4-x.Type: GrantFiled: November 2, 1995Date of Patent: September 16, 1997Assignee: Maxdem IncorporatedInventors: Matthew L. Marrocco, III, Ying Wang, Virgil J. Lee