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)
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Patent number: 6235867Abstract: The present invention provides a liquid crystal-aligning agent including, as the resin component, a polyimide precursor containing a chemical structure represented by the following formula (1): The present invention further provides a liquid crystal-aligning agent including, the above polyimide precursor and a polyimide precursor represented by the following general formula (2): (wherein Y is a tetravalent aliphatic group, Z is a bivalent aromatic group, and R is H or an alkyl group).Type: GrantFiled: November 5, 1999Date of Patent: May 22, 2001Assignee: Sumitomo Bakelite Company LimitedInventors: Toshimasa Eguchi, Toshiro Takeda
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Patent number: 6232428Abstract: Essentially colorless, transparent polyimide coatings and films prepared by combining aromatic dianhydrides with para-substituted aromatic diamines are provided. The polyimide coatings and films are produced by a process whereby the dianhydride and diamine monomer components are reacted at temperatures of greater than 80° C.Type: GrantFiled: January 14, 2000Date of Patent: May 15, 2001Assignee: I.S.T. CorporationInventors: Gary L. Deets, Toshiyuki Hattori
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Patent number: 6224892Abstract: Novel cross-linked polyesters of pyromellitic anhydride and a polyhydroxy compound containing more than two hydroxyl groups are highly water absorbent, and biodegradable, water swellable. The polyesters may be employed for the manufacture of medical devices such as prosthetic implants, supports for cell cultures or as wound dressings e.g. as a debriding agent.Type: GrantFiled: October 15, 1999Date of Patent: May 1, 2001Assignee: Smith & Nephew PlcInventor: Richard John Searle
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Patent number: 6222007Abstract: High quality films, preimpregnated tape (prepegs) and composites have been fabricated from polyimide precursor “salt-like” solutions. These “salt-like” solutions have a low viscosity (5,000 to 10,000 cp) and a high solids content (50-65% by weight) and can be coated onto reinforcing fiber to produce prepegs with excellent tack and drape at 12-15% residual solvent (˜4-6% water from thermal imidization reaction). The processing of these types of prepegs significantly overcomes solvent removal problems and allows excellent fiber wet out. In addition, the physical characteristics of the polyimide precursor “salt-like” solutions permits processing into high-performance materials through the use of standard prepregging and composite fabrication equipment. The resultant composites are of high quality.Type: GrantFiled: May 29, 1998Date of Patent: April 24, 2001Assignee: The United States of America as represented by the National Aeronautics and Space AdministrationInventors: Roberto J. Cano, Erik S. Weiser, Terry L. St. Clair, Yoshiaki Echigo, Hisayasu Kaneshiro
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Patent number: 6197920Abstract: The present invention relates to the synthesis of new type of diamine monomer, 1,3-bis(4-amonophenoxy)naphthalene, and with such a compound to produce a series of aromatic polymers, including polyamide, polyimide, copoly(amide-imide)s, etc., such polymers having excellent resistance to heat and mechanical properties.Type: GrantFiled: July 21, 1999Date of Patent: March 6, 2001Assignee: China Textile InstituteInventors: Kun Lin Cheng, Wen-Tung Chen
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Patent number: 6187899Abstract: A process for producing polyimide microfine particles which is amenable to free control of particle morphology and particle diameter distribution is provided. A polyamic acid and a polyimide, each in the form of microfine particles with good monodispersibility, are also provided. There is also provided a process for producing polyimide microfine particles from a tetracarboxylic anhydride and a diamine compound which comprises (a) a first step of preparing a first solution containing the tetracarboxylic anhydride and a second solution containing the diamine compound, (b) a second step of mixing the first and second solutions and causing a polyamic acid to precipitate in the form of microfine particles from the mixed solution under ultrasonic agitation, and (c) a third step of imidating the polyamic acid particles to provide the objective polyimide in the form of microfine particles.Type: GrantFiled: February 25, 1999Date of Patent: February 13, 2001Assignees: Osaka Prefectural Government, Sumitomo Bekelite Co., Ltd.Inventors: Katsuya Asao, Hidenori Saito
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Patent number: 6184333Abstract: The present invention is directed to polyimide systems which simultaneously offer low toxicity, a high glass transition temperature, excellent thermal oxidative stability, and desirable processing characteristics. These various polyimide systems include mixtures of monomeric reactants, polyimide-precursor reaction products, polyimides, and polyimide-containing articles. In one aspect of the invention, the mixture of monomeric reactants includes at least one dia-nhydride or a derivative thereof, and at least one diamine. The diamine may be 4,4′-[1,4-phenylene-bis(1-methylethylidene)]bisaniline, 4,4′-[1,3-phenylene-bis(1-methylethylidene)]bisaniline, and/or a derivative thereof. The diamine also may include a phenylenediamine, 2,2-bis[4-(4-aminophenoxyl)phenyl]propane, 4,4′(1,4-phenylene-bismethylene)bisaniline, and/or a derivative thereof. In addition, the mixture may include a reactive end-capping agent and/or a non-reactive end-capping agent.Type: GrantFiled: January 15, 1999Date of Patent: February 6, 2001Assignee: Maverick CorporationInventor: Robert A. Gray
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Patent number: 6184337Abstract: The present invention provide a novel polyimide which is soluble in organic solvents and excels in heat resistance, and to a process for producing the polyimide. The polyimide of the present invention comprises a repeating unit represented by the formula (1) and having a number average molecular weight of from 4,000 to 200,000. wherein X is —SO2— or —C(═O)—OCH2CH2O—C(═O)—, and R1, R2, R3 and R4 are independently an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.Type: GrantFiled: October 26, 1998Date of Patent: February 6, 2001Assignee: Tomoegawa Paper Co., Ltd.Inventors: Osamu Oka, Takeshi Nishigaya, Fumiyoshi Yamanashi
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Patent number: 6180746Abstract: A polyimide precursor solid residuum is an admixture of an aromatic dianhydride or derivative thereof and an aromatic diamine or dervative thereof plus a complexing agent, which is complexed with the admixture by hydrogen bonding. The polyimide precursor solid residuum is effectively employed in the preparation of polyimide foam and the fabrication of polyimide foam structures.Type: GrantFiled: May 21, 1999Date of Patent: January 30, 2001Assignees: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration, Unitika, LTDInventors: Erik S. Weiser, Terry L. St. Clair, Yoshiaki Echigo, Hisayasu Kaneshiro
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Patent number: 6166174Abstract: Polyimide copolymers were obtained containing 1,3-bis(3-aminophenoxy)benzene (APB) and other diamines and dianhydrides and terminating with the appropriate amount of a non-reactive endcapper, such as phthalic anhydride. Homopolymers containing only other diamines and dianhydrides which are not processable under conditions described previously can be made processable by incorporating various amounts of APB, depending on the chemical structures of the diamines and dianhydrides used. Polyimides that are more rigid in nature require more APB to impart processability than polyimides that are less rigid in nature. The copolymers that result from using APB to enhance processability have a unique combination of properties including: excellent thin film properties, low pressure processing (200 psi and below), improved toughness, improved solvent resistance, improved adhesive properties, improved composite mechanical properties, long term melt stability (several hours at 390 C.), and lower melt viscosities.Type: GrantFiled: August 5, 1999Date of Patent: December 26, 2000Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventor: Brian J. Jensen
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Patent number: 6160081Abstract: The invention relates to a photosensitive polyimide resin composition comprising (A) a polyamic acid having, in its main chain, repeating units formed from a polycondensation product of at least one tetracarboxylic acid or tetracarboxylic anhydride thereof with at least one diamine compound, and having actinic ray-sensitive functional groups at both terminals thereof; (B) a photosensitive auxiliary having a photopolymerizable functional group; (C) a photopolymerization initiator; and (D) a solvent, wherein 1 the polyamic acid is such that when the repeating unit represented by the formula (1) is defined as a unit molecular weight, a unit molecular weight per carboxyl group (unit molecular weight/COOH) falls within a range of from 200 to 300, and 2 the photosensitive resin composition permits the formation of a polyimide film having a residual stress of 40 MPa or lower and a coefficient of thermal expansion of 30 ppm/.degree. C.Type: GrantFiled: October 30, 1998Date of Patent: December 12, 2000Assignees: Nippon Zeon Co., Ltd., Fujitsu LimitedInventors: Akira Tanaka, Kei Sakamoto, Kenichi Ito, Yasuhiro Yoneda, Kishio Yokouchi, Yasuo Naganuma
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Patent number: 6150457Abstract: The present invention relates to compounds containing modified hydrazide groups and corresponding to formula I ##STR1## wherein R represents the residue obtained by removing the isocyanate groups from a monomeric polyisocyanate, a polyisocyanate adduct or an NCO prepolymer,X represents OR' or NHR' andR' represents a group which is inert to isocyanate groups under the conditions used to form the compound of formula I andn has a value of 2 to 6.The present invention also relates to one-component, thermoset coating compositions containing the compounds of formula I and a cross-linking component that is reactive with these compounds. Finally, the present invention relates coatings, sealants and adhesives prepared from these thermoset compositions.Type: GrantFiled: November 23, 1998Date of Patent: November 21, 2000Assignees: Bayer Corporation, Bayer AktiengesellscaftInventors: Sze-Ming Lee, Douglas A. Wicks, Eberhard Koenig, Carol L. Kinney, Karen M. Henderson
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Patent number: 6137008Abstract: A diamine which is useful in preparing a new flexible polyamide and polyimide with an aromatic dicarboxylic acid and a tetracarboxylic dianhydrides, respectively, has a general formula as follows: ##STR1## wherein R.sub.1 is methyl (--CH.sub.3) and n is an integer ranging from 1 to 4.Type: GrantFiled: June 2, 1999Date of Patent: October 24, 2000Assignee: National Science CouncilInventors: Der-Jang Liaw, Been-Yang Liaw
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Patent number: 6136949Abstract: A compound of the formula: ##STR1## wherein Ar.sup.Type: GrantFiled: September 3, 1998Date of Patent: October 24, 2000Assignee: The Dow Chemical CompanyInventors: Jimmy Dan Earls, Bruce L. Burton, Brenda Thies Colegrove
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Patent number: 6133401Abstract: Polyimide copolymers were obtained containing 1,3-bis(3-aminophenoxy)benzene (APB) and other diamines and dianhydrides and terminating with the appropriate amount of reactive endcapper. The reactive endcappers studied include but should not be limited to 4-phenylethynyl phthalic anhydride (PEPA), 3-aminophenoxy-4'-phenylethynylbenzophenone (3-APEB), maleic anhydride (MA) and nadic anhydride (5-norbornene-2,3-dicarboxylic anhydride, NA). Homopolymers containing only other diamines and dianhydrides which are not processable under conditions described previously can be made processable by incorporating various amounts of APB, depending on the chemical structures of the diamines and dianhydrides used. By simply changing the ratio of APB to the other diamine in the polyimide backbone, a material with a unique combination of solubility, Tg, Tm, melt viscosity, toughness and elevated temperature mechanical properties can be prepared.Type: GrantFiled: June 29, 1999Date of Patent: October 17, 2000Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventor: Brian J. Jensen
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Patent number: 6133408Abstract: A polyimide resin having good thermal stability and good adhesion to a metal foil is disclosed. The polyimide resin is prepared by dissolving at least one diamine in a polar aprotic solvent followed by the addition of an aromatic tetracarboxylic acid dianhydride to the solution of the aromatic diamines to prepare a polyamic acid solution, imidizing this solution to a polyimide resin by heating at a temperature above 250.degree. C., the polar aprotic solvent comprising at least 1 weight % of acetone. Polyimide laminates with a metal foil, such as a copper foil, are also described. The laminates may be used to form flexible printed circuit boards.Type: GrantFiled: January 15, 1999Date of Patent: October 17, 2000Assignee: Wirex CorporationInventors: Chien-Hwa Chiu, Der-Jen Sun, Yen-Huey Hsu, Fu-Ti Shiang, Chien-Hsiang Chen, Paul S. C. Wu
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Patent number: 6133407Abstract: A polyimide precursor solution having a high concentration yet low viscosity, a polyimide coating film having satisfactory physical properties which is prepared from the polyimide precursor solution, and a process for producing a polyimide coating film using the polyimide precursor solution. The polyimide precursor solution has dissolved therein a specific salt of a diamine and a tetracarboxylic acid and/or a dicarboxylic acid-dialkyl ester in a high concentration, the diamine and the tetracarboxylic acid and/or the dicarboxylic acid-dialkyl ester being capable of forming a polyimide. Also disclosed is a polyimide coating film obtained by heating the solution to cause imidization and a process for producing the polyimide coating film.Type: GrantFiled: June 23, 1998Date of Patent: October 17, 2000Assignee: Unitka Ltd.Inventors: Hisayasu Kaneshiro, Jushiro Eguchi, Yoshiaki Echigo, Takahiro Ono
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Patent number: 6127509Abstract: Polyimide polymers from 3,4,3',4'-biphenyltetracarboxylic dianhydride and 3,4,3',4'-benzophenonetetracarboxylic dianhydride and a diamine such as p-phenylenediamine exhibit a high glass transition temperature, high thermal oxidative stability and low moisture regain, useful for structural applications.Type: GrantFiled: June 1, 1999Date of Patent: October 3, 2000Assignees: E. I. du Pont de Nemours and Company, Fiberite Inc.Inventors: James F. Pratte, Murty S. Tanikella
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Patent number: 6114494Abstract: A fully imidized cresylic acid soluble polymer comprising 4,4'- oxydiphthalic anhydride (ODPA), 3,4,3',4',-biphenyltetracarboxylic dianhydride (BPDA), 3,4'-oxydianiline (ODA), and 4,4'-oxydianiline (DAPE) that can be used as a coating material such as a wire coated enamel. The polyimide has relatively low viscosity and high percent solids by substituting some of the 3,4'oxydianiline with 4,4'oxydianiline. Substitution with the 4,4'oxydianiline can be accomplished up to 25% on the molar basis without losing the fully imidized, cresol solubility characteristics.Type: GrantFiled: December 3, 1998Date of Patent: September 5, 2000Assignee: Ranbar Electrical Materials, Inc.Inventors: Edward W. Kifer, James R. Kwiecinski
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Patent number: 6111059Abstract: A diaminobenzene derivative represented by formula (1), and a polyimide obtained by reacting a diamine containing at least 1 mol % of said diaminobenzene derivative, with a tetracarboxylic acid and its derivatives to obtain a polyimide precursor and ring-closing it, having a repeating unit represented by formula (2), and a liquid crystal alignment film containing said polyimide. ##STR1## P is a single bond or --O--, --COO--, or --CONH--, Q is a cyclic substituent selected from an aromatic ring, an aliphatic ring, a hetero ring and their substitution products, R.sup.1 is an aliphatic ring, and R.sup.2 is C.sub.1-22 straight chain alkyl group, A is a tetravalent organic group constituting a tetracarboxylic acid, B is a bivalent organic group constituting a diamine.Type: GrantFiled: August 12, 1998Date of Patent: August 29, 2000Assignee: Nissan Chemical Industries, Ltd.Inventors: Takayasu Nihira, Hideyuki Nawata, Hiroyoshi Fukuro
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Patent number: 6103864Abstract: The polyimides are derived from solutions of at least one low-boiling organic solvent, e.g. isopropanol containing a mixture of polyimide-forming monomers. The monomeric solutions have an extended shelf life at ambient (room) temperatures as high as 80.degree. C. and consist essentially of a mixture of monoalkyl ester-acids, alkyl diester-diacids and aromatic polyamines wherein the alkyl radicals of the ester-acids are derived from lower molecular weight aliphatic secondary alcohols having 3 to 5 carbon atoms per molecule such as isopropanol, secondary butanol, 2-methyl-3-butanol, 2 pentanol or 3-pentanol. The solutions of the polyimide-forming monomers have a substantially improved shelf-life and are particularly useful in the aerospace and aeronautical industry for the preparation of polyimide reinforced fiber composites such as the polyimide cured carbon composites used in jet engines, missiles, and for other high temperature applications.Type: GrantFiled: January 14, 1999Date of Patent: August 15, 2000Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: William B. Alston, Gloria S. Gahn
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Patent number: 6100371Abstract: A polyimide for optical communications has a monomer, represented by the formula (1), as a repeating unit: ##STR1## wherein X.sub.1 and X.sub.2 are independently selected from the group consisting of halogen atom, halogenated alkyl group, halogenated aromatic ring group, --NO.sub.2, --OR.sup.1 and --SR.sup.1 (where R.sup.1 is selected from the group consisting of halogenated alkyl and halogenated aromatic ring groups); and Z is selected from the group consisting of divalent halogenated aliphatic hydrocarbon, divalent halogenated aliphatic cyclic hydrocarbon and divalent halogenated aromatic hydrocarbon. Thus, light absorption loss at a near infrared light wavelength range can be minimized by using the polyimide, so that the polyimide is very useful as an optical material in the optical communications field using light of a near infrared light region.Type: GrantFiled: September 18, 1998Date of Patent: August 8, 2000Assignee: SamSung Electronics Co., Ltd.Inventors: Dong-Hack Suh, Eun-Young Chung, Tae-Hyung Rhee
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Patent number: 6096850Abstract: Polyimide is produced by reacting two kinds of diamine compounds consisting of diaminopolysiloxane and a hydroxyl group-containing diamine or three kinds of diamine compounds consisting of diaminopolysiloxane, a hydroxyl group-containing diamine and an aromatic or alicyclic diamine with a 4,4'-(hexafluoroisopropylidene)diphthalic acid dianhydride, thereby once forming a polyamic acid, and subjecting the polyamic acid to polyimidization reaction. The resulting polyimide itself is soluble in low boiling organic solvents for general purpose use, typically methyl ethyl ketone. A photosensitive composition comprising the polyimide, a photo crosslinking agent and a photo acid-generating agent forms a negative type polyimide pattern upon development with an aqueous alkali solution.Type: GrantFiled: February 26, 1999Date of Patent: August 1, 2000Assignee: Nippon Mektron LimitedInventors: Lin-chiu Chiang, Jenq-Tain Lin, Nobuyuki Sensui
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Patent number: 6093790Abstract: The present invention provides polyimides and co-polyimides that are organosoluble. The polyimides and co-polyimides are prepared from an aromatic diamine having tert-butyl group, i.e., 1,4-bis(4-aminophenoxy)-2-tert-butyl-benzene, or its mixture with other diamines, and a mixture of dianhydrides that containing DSDA or 6FDA or other diether-dianhydrides.Type: GrantFiled: August 18, 1998Date of Patent: July 25, 2000Assignee: National Science CouncilInventors: Chin-Ping Yang, Huei-Wen Yang
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Patent number: 6084058Abstract: A composition for a polyimide type liquid crystal aligning film characterized in that a diamino compound constituting polyimide contains one, two or more diamine selected from 4,4'-diaminodiphenyl methane, 3,3'-dimethyl-4,4'-diaminodiphenyl methane, 2,2'-dimethyl-4,4'-diaminodiphenyl methane, 3,3',5,5'-tetramethyl-4,4'-diaminodiphenyl methane and 4,4'-ethylene di-meta-toluidine.Type: GrantFiled: September 11, 1998Date of Patent: July 4, 2000Assignee: Chisso CorporationInventors: Shizuo Murata, Toshiya Sawai, Satoshi Tanioka, Haruo Kato
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Patent number: 6084053Abstract: Electronic parts and a process for manufacturing the electronic parts are provided. The electronic parts comprise an electric insulating material exhibiting a high heat resistance and low dielectric constant as a structural component. The electric insulating material is formed of a polyimide containing a recurring unit represented by the following general formula (1).Type: GrantFiled: April 15, 1998Date of Patent: July 4, 2000Assignee: JSR CorporationInventors: Minoru Matsubara, Yasutake Inoue, Mayumi Kakuta, Igor Rozhanskii, Kohei Goto
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Patent number: 6080832Abstract: A diamine-containing polyamic acid alignment layer material provided by the polymerization of aromatic diamine and dianhydride, and having an excellent coating, adhesion and stability. After the polyamic acid alignment layer material is coated and cured at a high temperature, a polyamic acid alignment layer having a pretilt angle of below 2 degrees is formed due to a close ring reaction. The polyamic acid alignment layer with a low pretilt angle can be used in a TN (twisted nematic) type liquid crystal display.Type: GrantFiled: September 10, 1998Date of Patent: June 27, 2000Assignee: Industrial Technology Research InstituteInventors: Fu-Lung Chen, Ted Hong Shinn, Wen Hishin Wang, Chein-Dhau Lee
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Patent number: 6077924Abstract: Polyimide is produced by reacting two kinds of diamine compounds consisting of diaminopolysiloxane and a hydroxyl group-containing diamine or three kinds of diamine compounds consisting of diaminopolysiloxane, a hydroxyl group-containing diamine and an aromatic or alicyclic diamine with a dicarboxylic acid anhydride having a 2,5-dioxotetrahydrofuryl group as one acid anhydride group, thereby once forming a polyamic acid, and subjecting the polyamic acid to polyimidization reaction. The resulting polyimide itself is soluble in low boiling organic solvents for general purpose use, typically methyl ethyl ketone. A photosensitive composition comprising the polyimide, a photo crosslinking agent and a photo acid-generating agent forms a negative type polyimide pattern upon development with an aqueous alkali solution.Type: GrantFiled: February 26, 1999Date of Patent: June 20, 2000Assignee: Nipopon Mektron LimitedInventors: Lin-chiu Chiang, Jenq-Tain Lin, Nobuyuki Sensui
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Patent number: 6074757Abstract: The invention relates to mixtures of preferably from 80 to 99.9% by weight, based on the mixture, of a solution S1 comprising one or more polyamidocarboxylic acids and preferably from 0.1 to 20% by weight, based on the mixture, of a solution S2 comprising one or more, preferably primary, diamines and one or more tetracarboxylic acid diesters, processes for producing polyimide coatings using such mixtures, the use of such mixtures for producing polyimide coatings, and also polyamide-coated articles obtainable using such mixtures.Type: GrantFiled: February 17, 1998Date of Patent: June 13, 2000Assignee: Schenectady Europe GmbHInventors: Klaus-Wilhelm Lienert, Gerold Schmidt, Rainer Blum
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Patent number: 6069278Abstract: This invention relates the novel diamines, the polyimide oligomers and the polyimides derived therefrom and to the method of preparing the diamines, oligomers and the polyimides. The thermoplastic polyimides derived from the aromatic diamines of this invention are characterized as having a high glass transition temperature, good mechanical properties and improved processability in the manufacture of adhesives, electronic and composite materials for use in the automotive and aerospace industry. The distinction of the novel aromatic diamines of this invention is the 2,2',6,6'-substituted biphenyl radicals which exhibit noncoplanar conformation that enhances the solubility of the diamine as well as the processability of the polyimides, while retaining a relatively high glass transition temperature and improved mechanical properties at useful temperature ranges.Type: GrantFiled: November 23, 1999Date of Patent: May 30, 2000Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventor: Chun-Hua K. Chuang
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Patent number: 6066710Abstract: Disclosed is a method of making an imide-containing polymer by bulk or melt polymerizing monomers. A mixture is formed of (1) a cyclic compound that contains an anhydride group and a second group which is an anhydride, a carboxylic acid, or an ester and (2) a diamine in an amount stoichiometric .+-.5 mole % of stoichiometric with the amount of cyclic compound. An end capper may also be included in the mixture to control the molecular weight but no solvent is used. A polyimidesiloxane can be made by using a siloxane-containing diamine. The mixture is heated to a temperature above the T.sub.g or T.sub.m of the polymer but below its degradation temperature.Type: GrantFiled: October 29, 1998Date of Patent: May 23, 2000Assignee: Occidental Chemical CorporationInventors: Kevin H. Becker, Jerold C. Rosenfeld
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Patent number: 6063829Abstract: A treating method for liquid crystal alignment, which comprises applying polarized ultraviolet or electron rays to a polymer thin film formed on a substrate, in a predetermined direction relative to the substrate surface, and using the substrate to align liquid crystal without rubbing treatment, wherein the polymer thin film is a polyimide resin containing a repeating unit of the formula (I): ##STR1## (wherein R.sup.1 is a tetravalent organic group having an alicyclic structure, and R.sup.2 is a bivalent organic group), which is obtained by dehydration ring-closure of a polyimide precursor having a reduced viscosity of from 0.05 to 3.0 dl/g (in N-methyl-2-pyrrolidone at temperature of 300.degree. C. at a concentration of 0.Type: GrantFiled: September 4, 1998Date of Patent: May 16, 2000Assignee: Nissan Chemical Industries, Ltd.Inventors: Hideyuki Endou, Hiroyoshi Fukuro
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Patent number: 6060581Abstract: An optical alignment composition including self-photosensitive polyimide having a benzophenone moiety and an active hydrogen moiety, and an LCD having the alignment layer formed of the optical alignment composition are provided. Since the alignment layer with excellent thermal stability and improved pretilt angle is obtained, the LCD having excellent performance can be manufactured.Type: GrantFiled: December 10, 1997Date of Patent: May 9, 2000Assignee: Samsung Display Devices Co., Ltd.Inventors: Han-sung Yu, Yong-kyu Jang
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Patent number: 6060575Abstract: The present invention provides a series of easily processable poly(ether-imide)s that are organic-soluble and can afford colorless films, their organic solutions and their manufacturing process. The poly(ether-imide) is prepared from a dianhydride and a diamine, wherein the dianhydride is a bis(ether anhydride) having tert-butyl group, i. e. 1,4-bis(3,4-dicarboxyphenoxy)-2-tert-butylbenzene dianhydride.Type: GrantFiled: April 27, 1999Date of Patent: May 9, 2000Assignee: National Science CouncilInventors: Chin-Ping Yang, Sheng-Huei Hsiao
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Patent number: 6054554Abstract: The invention herein relates to a novel soluble polyimide resin comprising polyalicyclic structures and the process of preparation of the same, wherein aromatic tetracarboxylic dianhydride and novel aromatic diamine having an polyalicyclic group with various structures are used to yield a novel form of a polyimide resin, which has superior heat-resistance, solubility, and transparency.More specifically, the invention herein relates to a novel polyimide resin having excellent heat-resistance and solubility, which is prepared by means of reacting diamine monomers having a novel chemical structure with various types of aromatic carboxilic dianhydrides, in stead of aromatic diamine used for the preparation of the conventional polyimide resin. As a result, the polymers so obtained had the glass transition temperature of 260.degree. C..about.410.degree. C. and showed a increase in solubility in proportion to the increase in a number of the aromatic rings between two phenyl groups.Type: GrantFiled: May 7, 1999Date of Patent: April 25, 2000Assignee: Korea Research Institute of Chemical TechnologyInventors: Kil Yeong Choi, Mi Hie Yi, Wenxi Huang
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Patent number: 6048959Abstract: Tough, soluble, aromatic, thermoplastic copolyimides were prepared by reacting 4,4'-oxydiphthalic anhydride, 3,4,3',4'-biphenyltetracarboxylic dianhydride and 3,4'-oxydianiline. Alternatively, these copolyimides may be prepared by reacting 4,4'-oxydiphthalic anhydride with 3,4,3',4'-biphenyltetracarboxylic dianhydride and 3,4'-oxydiisocyanate. Also, the copolyimide may be prepared by reacting the corresponding tetra acid and ester precursors of 4,4'-oxydiphthalic anhydride and 3,4,3',4'-biphenyltetracarboxylic dianhydride with 3,4'-oxydianiline. These copolyimides were found to be soluble in common amide solvents such as N,N'-dimethyl acetamide, N-methylpyrrolidinone, and dimethylformamide allowing them to be applied as the fully imidized copolymer and to be used to prepare a wide range of articles.Type: GrantFiled: January 22, 1999Date of Patent: April 11, 2000Assignee: 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: 6046303Abstract: The invention herein relates to a soluble polyimide resin for a liquid crystal alignment layer and the manufacturing method thereof, wherein a mixture of aliphatic tetracarboxylic acid dianhydrides and aromatic diamine having aliphatic side chains are used to yield a soluble polyimide resin which has superior heat-resistance, solubility, surface hardness, transparency and liquid crystal alignment capacity.The soluble polyimide resin having alkoxy substituents, for a liquid crystal layer, according to the present invention, is manufactured by adding a mixture of dioxotetrahydrofuran 3-methylcyclohexene-1,2-dicarboxylic dianhydride, which is an aliphatic tetracarboxylic acid dianhydride and aromatic tetracarboxylic acid dianhydride to a mixture of aromatic diamine, and said dioxotetrahydrofuran 3-methylcyclohexene- 1,2-dicarboxylic dianhydride is used in the amount of 50 to 99 mol % to the total amount of anhydrides.Type: GrantFiled: September 11, 1998Date of Patent: April 4, 2000Assignee: Korea Research Institute of Chemical TechnologyInventors: Kil-Yeong Choi, Mi-Hie Yi, Moon-Young Jin, Jin-Tae Jung, Jeong-Ghi Koo, Jae-Eun Cho
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Patent number: 6040418Abstract: Fluorinated polymides comprising units of 2,2',5,5',6,6'-hexafluorobiphenyl-3,3',4,4'-tetracarboxylic dianhydride and aromatic diamines.Type: GrantFiled: August 4, 1998Date of Patent: March 21, 2000Assignee: Ube Industries, Ltd.Inventors: Tomohiko Yamamoto, Tatsuo Tsumiyama, Kouji Sugimoto
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Patent number: 6037499Abstract: This invention relates the novel diamines, the polyimide oligomers and the polyimides derived therefrom and to the method of preparing the diamines, oligomers and the polyimides. The thermoplastic polyimides derived from the aromatic diamines of this invention are characterized as having a high glass transition temperature, good mechanical properties and improved processability in the manufacture of adhesives, electronic and composite materials for use in the automotive and aerospace industry. The distinction of the novel aromatic diamines of this invention is the 2,2',6,6'-substituted biphenyl radicals which exhibit noncoplanar conformation that enhances the solubility of the diamine as well as the processability of the polyimides, while retaining a realatively high glass transition temperature and improved mechanical properties at useful temperature ranges.Type: GrantFiled: December 24, 1998Date of Patent: March 14, 2000Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventor: Chun-Hua K. Chuang
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Patent number: 6031061Abstract: A bis(trisubstitutedtrimellitic anhydride) derivative and a polyesterimide for optical communications, the polyesterimide being formed therefrom. The polyesterimide has a high refractive index, so that when using such polyesterimide as a material for a core of an optical fiber, the range of materials that can be selected for the cladding becomes wide. Also, a coating property and adhesion to a substrate are improved, thereby providing a good film forming property and thermal stability. Also, because the polyesterimide can minimize optical loss at a near infrared wavelength range, the polyesterimide is very useful as an optical material in the optical communications field adopting the light of near infrared wavelength.Type: GrantFiled: December 31, 1998Date of Patent: February 29, 2000Assignee: SamSung Electronics Co., Ltd.Inventors: Dong-hack Suh, Sun-young Chung, Tae-hyung Rhee
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Patent number: 6031068Abstract: The object of the present invention is to provide polyimide composition having such excellent property as low water absorption and low hygroscopic swelling, and a base tape for a TAB carrier tape and a FPC.The another object of the present invention is to provide polyimide composition comprising polyimide consisting of a repeating unit of the general formula (1): ##STR1## The further object of the present invention is to provide a base tape for a TAB carrier tape containing polyimide film made from said polyimide composition as a base film and a FPC containing polyimide film made from said polyimide composition as an insulating material.Type: GrantFiled: October 23, 1998Date of Patent: February 29, 2000Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventor: Kohji Okada
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Patent number: 6031067Abstract: The invention herein relates to a soluble polyimide resin and the process of preparation of the same, wherein aromatic tetracarboxylic dianhydride and aromatic diamine having an alicyclic group with various structures of substituted alkyl groups are used to yield a novel form of a polyimide resin, which has superior heat-resistance, solubility and transparency.More specifically, the invention herein relates to a novel polyimide resin having excellent heat-resistance and solubility, which is prepared by means of reacting aromatic diamine monomers having a novel chemical structure with various types of aromatic tetracarboxilic acid dianhydrides, in stead of aromatic diamine used for the preparation of the conventional polyimide resin. As a result, the polymers so obtained had the glass transition temperature of 250.degree. C..about.400.degree. C. and showed a increase in solubility in proportion to the increase in volume of the alkyl group.Type: GrantFiled: May 29, 1998Date of Patent: February 29, 2000Assignee: Korea Research Institute of Chemical TechnologyInventors: Kil-Yeong Choi, Mi-Hie Yi, Wenxi Huang
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Patent number: 6028159Abstract: A polyamideimide for optical communications, having a minimum light absorption loss in a near infrared light wavelength range, high thermal stability and excellent film processibility, and a method for preparing the same are provided. The polyamideimide has a higher refractive index than the conventional fluorinated polyamideimide. Thus, when using such polyamideimide as a material for a core of an optical fiber, the selection range on the material for cladding becomes wide. Also the coating property and adhesiveness to a substrate are improved, thereby providing a good film processibility and heat resistance.Type: GrantFiled: December 31, 1998Date of Patent: February 22, 2000Assignees: SamSung Electronics Co., Ltd., Korea Research Institute of Chemical TechnologyInventors: Dong-hack Suh, Eun-young Chung, Tae-hyung Rhee
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Patent number: 6025460Abstract: The service life of fiber-reinforced polyimide composites in a high temperature oxidative environment is extended by coating with a polyimide coating precursor solution that is synthesized by reacting an aromatic dianhydride with an aromatic diamine in a non-reactive solvent. The reactive solution is heated to a temperature sufficent to reduce its viscosity prior to its use as a coating. Preferably, a mixture of meta-phenylenediamine and para-phenylenediamine is reacted with biphenyldianhydride in n-methyl pyrrolidinone solvent and thereafter heated to between about 50.degree. C. (122.degree. F.) and 150.degree. C. (302.degree. F.) under nitrogen while stirring for a time sufficient to obtain a polyamic acid polyimide precursor coating solution having a Brookfield viscosity of from about 500 to about 5000 cP and a solids content of from about 5 to about 35 weight percent.Type: GrantFiled: November 4, 1997Date of Patent: February 15, 2000Assignee: Ohio Aerospace InstituteInventors: Anthony M. Mazany, Stanley G. Prybyla
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Patent number: 6025461Abstract: A photosensitive polyimide, which comprises a copolymer of (A) three diamine compounds mixture consisting of a diaminopolysiloxane, a hydroxyl group-containing diamine or carboxyl group-containing diamine and 1,4-bis[2-(3-aminobenzoyl)ethenyl]benzene with (B) an aromatic tetrocarboxylic acid dianhydride or a dicarboxylic anhydride having a 2,5-dioxotetrahydrofuryl group as one acid anhydride group, is soluble in all-purpose low boiling organic solvents, typically methyl ethyl ketone and provides a negative type photosensitive polyimide, which is developable with an aqueous alkaline solution.Type: GrantFiled: August 5, 1998Date of Patent: February 15, 2000Assignee: Nippon Mektron, LimitedInventors: Lin-Chiu Chiang, Jeng-Tain Lin
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Patent number: 6020456Abstract: Copolyetherimides are prepared by conventional means from hindered diamines such as the isomeric methyl-4,6-diethyl-1,3-phenylenediamines and bis(2-chloro-4-amino-3,5-diethylphenyl)methane. They have unusually high glass transition temperatures.Type: GrantFiled: November 6, 1998Date of Patent: February 1, 2000Assignee: General Electric CompanyInventors: Daniel Joseph Brunelle, Tina Lynn Grubb, Gordon Lee Tullos
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Patent number: 6013760Abstract: The invention herein relates to a soluble polyimide resin for a liquid crystal alignment layer and the process of preparation of the same, wherein aliphatic tetracarboxylic dianhydride and aromatic diamine having the amide group are used to yield a novel form of a polyimide resin having superior heat-resistance, solubility, transparency, and liquid crystal alignment capacity.More specifically, the invention herein relates to a novel polyimide resin having excellent heat-resistance, solubility, liquid crystal alignment property, and high pretilt angle, which is prepared by means of jointly using the aromatic diamine, used for the preparation of the conventional polyimide resin, and the aromatic diamine having a long alkyl chain with a substituted amide group, and reacting the same with various types of carboxylic dianhydride.Type: GrantFiled: May 29, 1998Date of Patent: January 11, 2000Assignee: Korea Research Institute of Chemical TechnologyInventors: Kil-Yeong Choi, Mi-Hie Yi, Moon-Young Jin, Dae-Woo Ihm, Jae-Min Oh
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Patent number: 6013759Abstract: A polyamideimide for optical communications, having a minimum optical loss in a near infrared light wavelength range, high thermal resistance and good film processibility, and a method for preparing the same are provided. The polyamideimide is very useful as an optical material in the optical communications field adopting the light of near infrared light wavelength.Type: GrantFiled: December 7, 1998Date of Patent: January 11, 2000Assignee: SamSung Electronics Co., Ltd.Inventors: Dong-hack Suh, Eun-young Chung, Tae-hyung Rhee
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Patent number: 6001942Abstract: The invention relates to a silicon-containing polyimide resin comprising (I) 0.1 to 100 mole % of structural units represented by the formula: ##STR1## where Ar.sup.1 is a tetra valent organic group having at least one aromatic ring, R independently represents a monovalent hydrocarbon group free of aliphatic unsaturated bonds, X is selected from an alkyleneoxyalkylene or an alkylene group having 2 or more carbon atoms, Y is an oxygen atom, an alkyleneoxyalkylene group, or an alkylene group having 2 or more carbon atoms, l, m, n are each integers having a value of 1 to 10, p is an integer having a value of 1 to 80, and a is 0 or 1; and (II) 99.9 to 0 mole % of structural units represented by the formula: ##STR2## where Ar.sup.2 is a tetravalent organic group having at least one aromatic ring, and Ar.sup.3 is a divalent organic group having at least one aromatic group.Type: GrantFiled: December 21, 1998Date of Patent: December 14, 1999Assignee: Dow Corning Toray Silicone Co., Ltd.Inventors: Masaaki Amako, Haruhiko Furukawa, Yoshitsugu Morita, Hiroshi Ueki
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Patent number: 6001910Abstract: A remoistenable hot melt adhesive composition comprising (i) 25 to 80% by weight of a sulfonated polyester;(ii) 3 to 40% by weight of an anionic or cationic plasticizer;(iii) 0 to 40% by weight of a polar tackifier;(iv) 0 to 3% by weight of an antioxidant; and(v) 10 to 35% by weight of a polar wax; and(vi) optionally 0 to 30% nonionic plasticizer, wherein the total of (i)-(vi) to equal 100% by weight.Type: GrantFiled: April 9, 1999Date of Patent: December 14, 1999Assignee: National Starch and Chemical Investment Holding CorporationInventors: Mitchell J. Blumenthal, Charles W. Paul, Matthew L. Sharak