Phosphorus- Or Sulfur-containing Reactant Patents (Class 528/352)
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Patent number: 4822853Abstract: An amphiphilic polyimide precursor having at least 70% by mole of the recurring unit of the formula (1): ##STR1## wherein R.sup.1 is a tetravalent group having at least 2 carbon atoms, R.sup.2 is a bivalent group having at least 2 carbon atoms, and R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are hydrogen atom or a monovalent group having 1 to 30 carbon atoms selected from an aliphatic group, an alicyclic group, an aromatic group, a group in which an aliphatic group is combined with an alicyclic group or an aromatic group, and their groups substituted by a halogen atom, nitro group, amino group, cyano group, methoxy group or acetoxyl group, provided that at least one, preferably at least two, of R.sup.3, R.sup.4, R.sup.5 and R.sup.Type: GrantFiled: July 15, 1986Date of Patent: April 18, 1989Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Masakazu Uekita, Hiroshi Awaji
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Patent number: 4808696Abstract: A method is provided for making organobis(thioether)s which include bis(thioetherimide)s and bis(thioetheranhydride)s. There is also provided alkylene bis(thioetherimide)s and the corresponding dianhydrides thereof which can be used to make crystalline polyimides.Type: GrantFiled: June 1, 1987Date of Patent: February 28, 1989Assignee: General Electric CompanyInventors: Tohru Takekoshi, Patricia P. Anderson, Thomas L. Evans
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Patent number: 4801682Abstract: High temperature fluorinated polyimides having repeating polymer units comprising ##STR1## wherein X is diamine. Typically, these polyimides are the copolymerization product of about 3 mole % to about 42 mole % nadic esters; about 39 mole % to about 49 mole % diamine; and about 17 mole % to about 48 mole % 4,4'9(2,2,2-trifluoro-1-phenylethylidene)-bipthalic tetra carboxylic acid dialkylester. These polimides provide the high strength properties at high temperatures yet they can be processed into solid polymers, fibers, films and composites at low temperatures and pressures.Type: GrantFiled: May 27, 1986Date of Patent: January 31, 1989Assignee: United Technologies CorporationInventor: Daniel A. Scola
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Patent number: 4785074Abstract: Homopolycondensates and copolycondensates of the group comprising linear, saturated polyamides, polyesters, polyamide-imides, polyester-imides and polyester-amides based on benzophenonedicarboxylic acids and benzophenonetricarboxylic acids are radiation-sensitive and are particularly suitable for the production of protective coatings and relief images.Type: GrantFiled: June 22, 1987Date of Patent: November 15, 1988Assignee: Ciba-Geigy CorporationInventor: Josef Pfeifer
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Patent number: 4783522Abstract: An aromatic polythioetherimide having a recurring unit of the following general formula (II): ##STR1## wherein --Ar--, which may be the same or different in the polymer, each represents a divalent aromatic residue and ##STR2## which may be the same or different in the polymer, each represents ##STR3## The aromatic polythioetherimides can be melt-molded, are excellent in the balance of mechanical properties and heat resistance, and can be widely used for parts in the electric and electronic fields, housings, automobile parts, aircraft interior parts, sliding parts, gears, cams, insulating materials, heat-resistant films, heat-resistant varnishes, heat-resistant fibers, etc., and preferably can be used as an engineering plastic for gears, cams, etc., and a heat-resistant insulating film material for electronic hardwares.Type: GrantFiled: July 11, 1986Date of Patent: November 8, 1988Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Mitsutoshi Aritomi, Makoto Terauchi
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Patent number: 4778859Abstract: A curable composition comprising (a) a curable polyimide soluble in organic solvents and (b) a polymerization initiator as essential components, said polyimide consisting of recurring units represented by the formula ##STR1## wherein, each of X, X.sub.1, X.sub.2, X.sub.3 and X.sub.4 is a tetravalent carbocyclic or heterocyclic residue, each of Y.sub.1, Y.sub.2, and Y.sub.3 is a divalent carbocylic or heterocyclic residue, at least one of Z.sub.1 and Z.sub.2 is a residue having a reactive carbon-carbon double bond, and each of l, m, and n is an integer from 0 to 20, preferably from 0 to 10. The polyimide may include (a) polyacrylate compounds (b) bis-imide compounds (c) photosensitive polyimide precursors (d) oxime initiators (e) a 3 component sensitizer of a phenone compound, a mercapto compound, and an arylamine-alkanol, or mixtures of a,b,c,d, and e.Type: GrantFiled: April 28, 1986Date of Patent: October 18, 1988Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hideo Ai, Akihiko Ikeda, Kan-ichi Yokota
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Patent number: 4774317Abstract: Polyetherimides are provided having chemically combined alkylaryl diamine units and method for making. The polyetherimides have similar T.sub.g 's over broad mol percent ranges to polyetherimides made from phenylene diamine units while providing economic cost advantages during manufacture.Type: GrantFiled: October 20, 1986Date of Patent: September 27, 1988Assignee: General Electric CompanyInventors: John W. Verbicky, Jr., Elbridge A. O'Neil
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Patent number: 4772678Abstract: Novel liquid crystalline extended chain polymer compositions comprising a high concentration of one or more extended chain homopolymer(s), copolymer(s), or block polymer(s) and certain strong acids are prepared by admixing a high concentration of one or more selected homo- or hetero-bifunctional monomer(s) with or without oxidation protecting atoms or groups and one or more of a substantially non-oxidizing strong acid(s) having a high or low P.sub.2 O.sub.5 content. Such compositions are capable of exhibiting excellent cohesive strength, and are especially suited to the production of high molecular weight ordered polymer fibers by dry-jet wet spinning. These liquid crystalline compositions are capable of being drawn through long air gap distances and spun at exceptionally high spin draw ratios. Fibers, films and other articles formed from these liquid crystalline compositions exhibit exceptionally high physical and heat resistant properties.Type: GrantFiled: August 5, 1985Date of Patent: September 20, 1988Assignee: CommTech International Management CorporationInventors: Joanne R. Sybert, James F. Wolfe, Paul D. Sybert, Blake Wilson
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Patent number: 4760126Abstract: A polyimide or polyamic acid synthesized from a diamine, which may be fluorinated, and a dianhydride of the following formula: ##STR1## where R.sub.f =perfluoroalkylene and Y.sub.1 and Y.sub.2 are independently oxy-carbonyl or thiocarbonyl.Type: GrantFiled: September 8, 1986Date of Patent: July 26, 1988Assignees: Hitachi, Ltd., Hitachi Chemical Co. Ltd.Inventors: Shunichi Numata, Koji Fujisaki, Noriyuki Kinjo
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Patent number: 4755585Abstract: Novel polymers and molding compositions are prepared from acyl halide derivatives of tricarboxylic acids and diamines and about 1 to about 10 percent by weight of phthalic anhydride, trimellitic anhydride or aniline moieties. The polymers are useful in engineering plastics.Type: GrantFiled: July 25, 1986Date of Patent: July 5, 1988Assignee: Amoco CorporationInventors: Robert B. Hanson, Jeffrey D. Felberg, Gary T. Brooks
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Patent number: 4749777Abstract: A liquid crystal aligning agent consisting essentially of a polyimide resin obtained by the polymerization of a diamine, a tetracarboxylic acid dianhydride and a monoamine of the formula:R.sup.2 (R.sup.1).sub.n NH.sub.2 (I)wherein R.sup.1 is a divalent organic group, R.sup.2 is an alkyl group having from 6 to 20 carbon atoms, and n is 0 or 1.Type: GrantFiled: June 11, 1987Date of Patent: June 7, 1988Assignee: Nissan Chemical Industries Ltd.Inventors: Noriaki Kohtoh, Toyohiko Abe, Hiroyoshi Fukuro
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Patent number: 4746720Abstract: Solvent resistant polyimides are provided having improved T.sub.g by effecting reaction between aromatic bis(anhydride), such as aromatic bis(etheranhydride), and benzofuran amine such as 2-(4-aminophenyl)-5-benzofuranamine.Type: GrantFiled: October 20, 1986Date of Patent: May 24, 1988Assignee: General Electric CompanyInventor: Donald R. Berdahl
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Patent number: 4742150Abstract: Polyetheramideimide is provided and method for making. There are utilized aromatic bis(etheranhydride) and diaminobenzanilide or mixtures thereof with an organicdiamine. The polyetheramideimide has been found to have improved solvent resistance.Type: GrantFiled: September 25, 1986Date of Patent: May 3, 1988Assignee: General Electric CompanyInventors: John W. Verbicky, Jr., Elbridge A. O'Neil, Mark J. Bausch
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Patent number: 4742152Abstract: High temperature fluorinated polyimides having repeating polymer units of the formula ##STR1## wherein X is aromatic or aliphatic. The polyimides can be made by oxidizing 1-phenyl-1,1-bis (3,4-xylyl)-2,2,2-trifluorethane to form 4,4'(2,2,2-trifluoro-1-phenylethylidene)biphthalic tetra carboxylic acid and dehydrating that to form 4,4'(2,2,2-trifluoro-1-phenyl-ethylidene-biphthalic tetra carboxylic acid dianhydride. The dianhydride is polymerized with a diamine to form a polyamic acid which is further imidized to the polyimide. Alternatively, the dianhydride can be esterified to form a 4,4'(2,2,2-trifluoro-1-phenylethylidene)-biphthalic tetracarboxylic acid dialkylester which is then polymerized with a diamine to form a polyamic acid which can then be imidized to a polyimide.Type: GrantFiled: May 27, 1986Date of Patent: May 3, 1988Assignee: United Technologies CorporationInventor: Daniel A. Scola
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Patent number: 4736015Abstract: Aromatic polyimide compositions, useful in particular for manufacturing adhesive materials, varnishes and films withstanding high temperatures, having a high solubility in organic solvents, particularly polar solvents and which are manufactured by reacting, in such a solvent, a tetraester or diacid-diester of benzhydrol 3,3', 4, 4' tetracarboxylic acid with an aromatic diamine for a sufficient time to obtain a polycondensation reaction product having an inherent viscosity at 30.degree. C., at a concentration of 5 g/liter in N-methyl pyrrolidone, ranging from 0.1 to 2 dl/g.Type: GrantFiled: October 19, 1982Date of Patent: April 5, 1988Assignee: Institut Francais du PetroleInventors: Guy Rabilloud, Michel Senneron, Choua Cohen, Paul Mariaggi, Bernard Sillion
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Patent number: 4728697Abstract: Carboxy-terminated prepolymers are prepared by the reaction of a diamine, preferably an aromatic diamine, or a mixture thereof with a triamine, with a carboxy anhydride such as trimellitic anhydride and a dianhydride such as bisphenol A dianhydride. The prepolymers, or functional derivatives thereof, are then reacted with a diisocyanate or diamine, or a mixture thereof with a triisocyanate or triamine, preferably an aromatic diisocyanate, to produce copolyamideimides. The products prepared using triamines or triisocyanates are crosslinked. Other products containing alkyl or alicyclic groups attached to aromatic radicals can be oxidatively crosslinked, e.g., by heating in air.Type: GrantFiled: September 27, 1985Date of Patent: March 1, 1988Assignee: General Electric CompanyInventors: Donald A. Bolon, Thomas B. Gorczyca
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Patent number: 4725642Abstract: Melt-fusible copolyimides based on pyromellitic anhydride and two defined classes of aromatic diamines, at least one diamine of each class being incorporated into the polyimide, each diamine class being present in an amount of 10-90 mole percent of the total diamine content (100 mole percent), melt below about 400.degree. C. and can be fabricated into articles, or can be applied to either fibrous or nonfibrous substrates to make prepregs, tapes, etc., which then are shaped into final articles, such as printed circuit boards or aircraft panels.Type: GrantFiled: April 29, 1985Date of Patent: February 16, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventors: Thomas P. Gannett, Robert J. Kassal, Rolland S. Ro, Julius Uradnisheck
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Patent number: 4724257Abstract: An aromatic polythioetheramide-imide having a recurring unit of the following general formula (II): ##STR1## wherein --Ar--, which may be the same or different in the polymer, each represents a divalent aromatic residue. The aromatic polythioetheramide-imides are excellent in the balance of mechanical properties, heat resistance and moldability and can be used widely for parts in electric and electronic fields, housings, automobile parts, aircraft interior parts, sliding parts, gears, insulating materials, heat-resistant films, heat-resistant varnishes, heat-resistant fibers, etc.Type: GrantFiled: July 14, 1986Date of Patent: February 9, 1988Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Mitsutoshi Aritomi, Makoto Terauchi
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Patent number: 4716216Abstract: Crystalline polyimides having low glass transition temperatures and high solvent resistance are obtained by reacting diamino-oligo-phenylene sulfides with aromatic tetracarboxylic acids or their anhydride derivatives. The diamino-oligo-phenylene sulfides can be of varying length and can be reacted with the dianhydride by conventional processes.Type: GrantFiled: November 19, 1986Date of Patent: December 29, 1987Assignee: General Electric CompanyInventors: Tohru Takekoshi, Patricia P. Anderson
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Patent number: 4703103Abstract: Novel compositions comprising a high concentration of one or more extended chain homopolymer, copolymer, or block polymer and certain polyphosphoric acids are prepared under conditions to exercise control of molecular weight as characterized by intrinsic visoscity. Such compositions are optically anisotropic (liquid crystlaline), capable of exhibiting excellent cohesive strength, and are especially suited to the production of high molecular weight ordered polymer fibers by dry-jet wet spinning. These liquid crystalline compositions are capable of being drawn through long air gap distances and spun at excptionally high spin draw ratios. Fibers, films and other articles formed from these liquid crystalline compositions exhibit exceptionally high physical and heat resistant properties.Type: GrantFiled: March 16, 1984Date of Patent: October 27, 1987Assignee: CommTech InternationalInventors: James F. Wolfe, Paul D. Sybert
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Patent number: 4689391Abstract: A process for making polyetherimides involving reacting an aromatic bis(ether anhydride) with an organic diamine in the presence of a solvent so as to form a polyamide acid. The polyamide acid is thereafter polymerized in a solid state at a temperature below the glass transition temperature of the final polyetherimide.Type: GrantFiled: December 21, 1984Date of Patent: August 25, 1987Assignee: General Electric CompanyInventors: Edward N. Peters, Daniel W. Fox
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Patent number: 4687836Abstract: This invention relates to a polyimide powder in use for adhesion and/or coat forming and to a method of preparing said powder, wherein polyamic-acid is chemically imidized which is obtained by reacting tetracarboxylic acid dianhydride with diamine in organic solvents.This invention further relates to a method for adhesion and coat forming by using said polyimide powder.This invention still further relates to a method for preparing prepreg by using said polyimide powder, and a method for adhesion and preparing molded laminates by using said prepreg.Type: GrantFiled: October 10, 1985Date of Patent: August 18, 1987Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Akira Ibi, Takushi Sato, Akihiro Yamaguchi, Shigeru Takahashi, Shigeyuki Shishido, Shoji Tamai, Hisai Nakajima
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Patent number: 4681928Abstract: Aromatic or aliphatic dianhydrides and/or acid anhydrides are reacted with certain aromatic diamines alone or in combination with other diamines to produce polyimides, polyamide acids, poly(amide-imides), poly(amide-amide acids), poly(esterimides) or poly(esteramide acids). These polymers are thermoplastic in nature and have improved processing characteristics and thermal stability. The polymers may be prepared by either melt or solution polymerization techniques.Type: GrantFiled: June 1, 1984Date of Patent: July 21, 1987Assignee: M&T Chemicals Inc.Inventors: Abe Berger, Rohitkumar H. Vora
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Patent number: 4680373Abstract: The present invention provides a process for the production of random copolymers containing repeating polyimide units and repeating polyetherimide units. The process is a reverse addition process and utilizes at least two dianhydrides of varying reactivity.Type: GrantFiled: May 27, 1986Date of Patent: July 14, 1987Assignee: General Electric CompanyInventors: Patrick E. Gallagher, Ronald A. Greenberg
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Patent number: 4654415Abstract: Oligomeric and/or polymeric radiation-sensitive polyimide and polyisoindoloquinazoline dione precursors which are soluble in organic solvents, and are of high purity, i.e. in particular chloride-free, are produced simply by first reacting an aromatic and/or heterocyclic tetracarboxylic acid dianhydride with an olefinically unsaturated alcohol to an olefinically unsaturated tetracarboxylic acid diester, and then reacting the latter, in the presence of a carbodiimide, with a diamino compound or a diamino compound having at least one ortho-positioned amino group. The radiation-sensitive precursors thus produced are suitable, for instance, for the production of highly heat-resistant relief structures.Type: GrantFiled: March 27, 1985Date of Patent: March 31, 1987Assignee: Siemens AktiengesellschaftInventors: Hellmut Ahne, Eberhard Kuhn
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Patent number: 4647616Abstract: Thermosettable prepolymers are prepared by reacting (A) a heterocyclic material containing one or more rings and one nitrogen atom or a mixture of such materials wherein at least one of such materials contains at least two reactive substituent groups having at least one reactive hydrogen atom attached to a carbon atom which is attached to the ring such as 2,4,6-trimethyl pyridine; with (B) a cycloaliphatic or aromatic carboxylic acid mono- or dianhydride such as phthalic anhydride. These prepolymers or resins, can be homopolymerized without coreactants or copolymerized with N,N'-bis-imide such as 1,1'-(methylenedi-4,1-phenylene)bismaleimide, to produce products, mat castings or composites having good mechanical and thermal properties.Type: GrantFiled: July 15, 1985Date of Patent: March 3, 1987Assignee: The Dow Chemical CompanyInventors: Loren L. Swearingen, Jimmy D. Earls, Randy J. LaTulip
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Patent number: 4645823Abstract: A process for preparing polyamides which comprises polycondensing dicarboxylic acids having the following general formula and diamines by using carbodiimides as the condensing agent. ##STR1## wherein X is a group having a valence of (m+2), and C.sub.6-20 carbocyclic group, C.sub.3-20 heterocyclic group, C.sub.2-20 alkyl group, or C.sub.2-20 alkenyl group, the group having at least one carbon-carbon double bond in the position of conjugating to carboxylic acid radical or the group having an .alpha.,.beta.-unsaturated ketone structure;Y is --OR or --NRR' wherein R and R' each independently is C.sub.5-20 carbocyclic group, C.sub.1-20 heterocyclic group, C.sub.1-20 alkyl group or substituted group thereof having at least one substituent selected from the group consisting of --OW (wherein W is C.sub.1-12 alkyl group), C.sub.2-12 saturated acyl group, C.sub.2-12 saturated acyloxy group, C.sub.2-12 saturated acylamino group, C.sub.2-12 dialkylamino group, --SW (wherein W is the same as defined above), C.sub.Type: GrantFiled: September 10, 1985Date of Patent: February 24, 1987Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hideo Ai, Akihiko Ikeda, Yoshio Matsuoka
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Patent number: 4629777Abstract: Homopolyimides and copolyimides of aromatic tetracarboxylic acids and aromatic diamines which are substituted in the two ortho-positions relative to at least one N atom by alkyl, alkoxy, alkoxyalkyl, cycloalkyl or aralkyl, are soluble in organic solvents and have increased glass transition temperatures and hence very good heat stabilities. Such polyimides, which contain radicals of a benzophenonetetracarboxylic acid, are radiation-sensitive and autophotocrosslinkable. The polyimides are suitable for the production of films, protective coatings and photographic relief images.Type: GrantFiled: May 10, 1984Date of Patent: December 16, 1986Assignee: Ciba-Geigy CorporationInventor: Josef Pfeifer
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Patent number: 4625013Abstract: Aromatic sulfoxy tetracarboxylic acids, and their derivatives such as dianhydrides, bisimides and polyimides, are prepared by oxidizing the corresponding sulfides under relatively mild conditions, using oxidizing agents such as nitric acid, N-chlorosuccinimide, potassium persulfate and hydrogen peroxide. The polyimides may also be prepared by the reaction of the dianhydrides or certain bisimides with diamines.Type: GrantFiled: December 20, 1984Date of Patent: November 25, 1986Assignee: General Electric CompanyInventors: Thomas L. Evans, Marsha M. Grade
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Patent number: 4622285Abstract: Oligomeric and/or polymeric polyoxazole and polythiazole precursors can be prepared with high purity, i.e., especially without chloride, in a simple manner if an aromatic and/or heterocyclic dihydroxy, dialkoxy or diaryloxydiamino compound or a corresponding dithio compound is reacted with a dicarboxylic acid in the presence of a carbodiimide. The precursors prepared in this manner are suitable, for instance, for the manufacture of protection and insulating layers.Type: GrantFiled: March 27, 1985Date of Patent: November 11, 1986Assignee: Siemens AktiengesellschaftInventor: Hellmut Ahne
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Patent number: 4613637Abstract: A copolymer formed from an isoimide oligomer and another compound, such as an aryl sulfone, each of which has reactive functional terminal groups, such as ethylenic or acetylenic groups. The isoimide oligomer is soluble in the other compound, unreactive with the compound below a certain temperature and forms a liquid blend therewith. Upon heating the liquid blend above that certain temperature, the terminal groups on the isoimide oligomer and the other compound react with each other to form a copolymer. The liquid blends may be used to form encapsulants, coatings, films, and resin matrices for composites to provide resins with excellent high temperature properties.Type: GrantFiled: December 27, 1983Date of Patent: September 23, 1986Assignee: Hughes Aircraft CompanyInventors: Abraham L. Landis, Arthur B. Naselow
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Patent number: 4609712Abstract: Bis(dicarboxyphenyl) sulfone compounds, including the free tetracarboxylic acids and their functional derivatives such as salts, esters, amides, anhydrides and imides, are prepared by oxidizing the corresponding sulfides with a relatively strong oxidizing agent, preferably a peroxy reagent such as acetyl peroxide or m-chloroperbenzoic acid. The reaction is especially useful for the preparation of sulfone polyimides, since films of the sulfide polyimides may be oxidized without dissolving or otherwise degrading their structural integrity.Type: GrantFiled: June 18, 1984Date of Patent: September 2, 1986Assignee: General Electric CompanyInventors: Thomas L. Evans, Marsha M. Grade
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Patent number: 4599396Abstract: Crystalline polyetherimides having equilibrium melting points below 400.degree. C. are obtained by the reaction of various p-linked polycyclic tetracarboxylic acids or their functional derivatives with p-linked polycyclic diamines. The structural units in said crystalline polyetherimides contain at least 7 aromatic rings.Type: GrantFiled: September 4, 1984Date of Patent: July 8, 1986Assignee: General Electric CompanyInventors: Tohru Takekoshi, Patricia P. Anderson
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Patent number: 4588804Abstract: A soluble polyimide derived from dehydration of a polyamic acid which is the liquid phase condensation reaction product of a solution in aprotic solvent of approximately equimolar amounts of aromatic dianhydride and aromatic diamine. At least 50 mole % of the dianhydride must have ring linkages which prevent conjugation between the rings and at least 20 mole % of the diamine must contain electron withdrawing groups.Type: GrantFiled: May 4, 1984Date of Patent: May 13, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: Michael Fryd
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Patent number: 4588805Abstract: Sulfonate-terminated polyimides and polyamic acids are prepared by the reaction of a dianhydride such as bisphenol A dianhydride, a diamine such as m-phenylenediamine or bis(4-aminophenyl)methane, and an amino sulfonic acid such as p- or m-aminobenzenesulfonic acid or 2-aminoethanesulfonic acid. The products may be used as compatibilizing agents for blends of aromatic polymers with ionomeric elastomers.Type: GrantFiled: September 6, 1984Date of Patent: May 13, 1986Assignee: General Electric CompanyInventor: Robert E. Williams, Jr.
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Patent number: 4587324Abstract: Compounds having the general formula 1 ##STR1## wherein X and Y are functional groups, preferably amino groups, are polymerized with, for example, polyfunctional epoxides to provide heat and fire resistant polymers useful for making flame and fire resistant polymer structures such as for aircraft secondary structures. The groups R in 1 are preferably alkyl and lower halo (e.g., chloro) alkyl.Type: GrantFiled: August 16, 1984Date of Patent: May 6, 1986Assignee: The United States of America as represented by the Administrator, National Aeronautics and Space AdministrationInventors: John A. Mikroyannidis, Demetrius A. Kourtides
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Patent number: 4556697Abstract: Nylon-type polyamides are produced by the polycondensation of a non-wholly aromatic diacid and diamine in the presence of a poly(ethylene oxide) matrix.Type: GrantFiled: July 25, 1983Date of Patent: December 3, 1985Assignee: The Standard Oil CompanyInventors: Benedict S. Curatolo, Gerald P. Coffey
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Patent number: 4552931Abstract: A process of endcapping a polyimide system with an endcapping agent in order to achieve a controlled decrease in molecular weight and melt viscosity along with predictable fracture resistance of the molded products is disclosed. The uncapped system is formed by combining an equimolar ratio of 4,4'-bis(3,4-dicarboxyphenoxy) diphenylsulfide dianhydride (BDSDA) and 1,3-bis(aminophenoxy)benzene (APB) dissolved in bis(2-methoxyethyl)ether. The endcapped system is formed by dissolving APB in bis-(2-methoxyethyl)ether, adding the endcapping agent, and then adding the BDSDA. By varying the amount of endcapping from 0 to 4%, molecular weight is decreased from 13,900 to 8660. At a processing temperature of 250.degree. C., there is a linear relationship between molecular weight and viscosity, with the viscosity decreasing by two orders of magnitude as the molecular weight decreased from 13,900 to 8660. A greater drop in viscosity is noted at higher temperatures.Type: GrantFiled: September 11, 1984Date of Patent: November 12, 1985Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Terry L. St. Clair, Harold D. Burks
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Patent number: 4551522Abstract: A process for the synthesis of the photosensitive polyamic acid derivatives which are polyimide precursors, comprising the sequential steps:(1) Partially derivatizing an aromatic dianhydride with a reactive monomer containing a photosensitive moiety;(2) Condensation polymerizing the partially derivatized aromatic dianhydride with aromatic diamine to form polyamic acid;(3) Isoimidization of the polyamic acid;(4) Condensation of the polyisoimide to polyamic acid derivative by reaction with additional reactive monomer; and(5) Separation of the polyamic acid derivative.Type: GrantFiled: April 26, 1985Date of Patent: November 5, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventors: Michael Fryd, David L. Goff
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Patent number: 4550156Abstract: This invention is concerned with a new class of polyetherimide copolymers. More particularly, the invention is concerned with polyetherimide copolymers containing polyetherimide repeating units and repeating polyimide units. The polyetherimide compositions have improved solvent resistance and good heat properties.Type: GrantFiled: October 26, 1984Date of Patent: October 29, 1985Assignee: General Electric CompanyInventor: Patrick E. Gallagher
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Patent number: 4536565Abstract: Phosphorus-containing polyimides and copolyimides are synthesized in a two-step polycondensation reaction from 1-[(diorganooxyphosphonyl)methyl]-2,4- and -2,6-diaminobenzenes and tetracarboxylic anhydride. The diorgano position of the diorganooxyphosphonyl group includes alkyl, such as ethyl, substituted alkyl, such as 2-chloroethyl, and aryl such as phenyl. The tetracarboxylic anhydrides include compounds such as pyromellitic dianhydride and benzophenone tetracarboxylic dianhydride. The glass transition temperature (Tg) of the polyimides is reduced by incorporation of the (dialkoxyphosphonyl)methyl groups. Both the molecular weight and the thermal stability of the polymers are reduced with increasing concentration of the phosphorus moieties.Type: GrantFiled: August 16, 1984Date of Patent: August 20, 1985Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventor: John A. Mikroyannidis
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Patent number: 4536560Abstract: Cyclic dianhydrides and polyimides are prepared from maleic anhydride compounds and diolefins. The diolefins are alpha- , omega-linear diolefins of up to 100 carbon atoms or cyclic diolefins of up to 40 carbon atoms. The polyimides and copolyimides prepared from these cyclic dianhydrides are useful in films, fibers and coatings.Type: GrantFiled: May 29, 1984Date of Patent: August 20, 1985Assignee: Standard Oil Company (Indiana)Inventors: Mark L. Winzenburg, Ellis K. Fields, Benjamin L. Shneider
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Patent number: 4533693Abstract: Novel compositions comprising a high concentration of one or more extended chain homopolymer, copolymer, or block polymer and certain polyphosphoric acids are prepared. Such compositions are optically anisotropic (liquid crystalline), capable of exhibiting excellent cohesive strength, and are especially suited to the production of high molecular weight ordered polymer fibers by dry-jet wet spinning. These liquid crystalline compositions are capable of being drawn through long air gap distances and spun at exceptionally high spin draw ratios. Fibers, films and other articles formed from these liquid crystalline compositions exhibit exceptionally high physical and heat resistant properties.Type: GrantFiled: September 15, 1983Date of Patent: August 6, 1985Assignee: SRI InternationalInventors: James F. Wolfe, Paul D. Sybert, Joanne R. Sybert
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Patent number: 4530993Abstract: Disclosed is a polyimide film consisting essentially of 2,2'-dichloro-4,4'-biphenylene pyromellitimide units. This film has high tensile characteristics and excellent heat resistance.Type: GrantFiled: November 2, 1984Date of Patent: July 23, 1985Assignee: Director General of Agency of Industrial Science & TechnologyInventors: Takuma Jinda, Toshikazu Matsuda, Masanori Sakamoto
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Patent number: 4499252Abstract: A process for producing a polyimide precursor having excellent adhesion property and improved moisture resistance by polymerization of an organic tetracarboxylic acid component and a diamine is disclosed. A portion of the organic tetracarboxylic acid is reacted with an aminosilane compound in which H in an amino group is substituted with a monovalent organic group containing a hydrophobic aromatic ring, to produce a silane-modified polycarboxylic acid component and the resulting silane-modified polycarboxylic acid component is polymerized with a diamine together with the residual organic tetracarboxylic acid component.Type: GrantFiled: March 28, 1984Date of Patent: February 12, 1985Assignee: Nitto Electric Industrial Co., Ltd.Inventors: Kazumasa Igarashi, Katsuhiko Yamaguchi, Munekazu Tanaka
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Patent number: 4499260Abstract: Method of forming 4,4',4",4'"-tetraamino phthalocyanines by reducing 4,4',4",4'"-tetranitro phthalocyanines, polymerization of the metal tetraamino phthalocyanines with a tetracarboxylic dianhydride (preferably aromatic) or copolymerization with a tetracarboxylic dianhydride and a diamine (preferably also aromatic) to produce amic acids which are then dehydrocyclized to imides. Thermally and oxidatively stable polymers result which form tough, flexible films, etc.Type: GrantFiled: November 10, 1982Date of Patent: February 12, 1985Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Bappalige N. Achar, George M. Fohlen, John A. Parker
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Patent number: 4496711Abstract: Processes for forming a class of relatively low molecular-weight oligomers containing at least one isoimide group and terminal groups capable of undergoing an addition polymerization reaction are provided. These oligomers are characterized by excellent solubility in common solvents and a melting temperature considerably lower than their cure temperature, thus enabling the oligomers to be formed into cured polymers more slowly and at lower temperatures, all without the evolution of deleterious gases. The process for forming these oligomers includes the formation of a polyamic acid and dehydration thereof under specified conditions to effect cyclization of the polyamic acid to form the isoimide-containing oligomer, without the formation of undesired side-reaction products.Type: GrantFiled: September 26, 1983Date of Patent: January 29, 1985Assignee: Hughes Aircraft CompanyInventor: Abraham L. Landis
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Patent number: 4495342Abstract: A class of relatively low molecular-weight oligomers containing at least one isoimide group and terminal groups capable of undergoing an addition polymerization reaction are provided. These oligomers are characterized by excellent solubility in common solvents and a melting temperature considerably lower than their cure temperature, thus enabling the oligomers to be formed into cured polymers more slowly and at lower temperatures, all without the evolution of deleterious gases. The oligomers of the present invention may be formed by reacting an aromatic dianhydride with an aromatic diamine, followed by reaction with a monoanhydride. The resulting product is dehydrated to form the isoimide-containing oligomer.Type: GrantFiled: September 26, 1983Date of Patent: January 22, 1985Assignee: Hughes Aircraft CompanyInventor: Abraham L. Landis
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Patent number: 4489185Abstract: Novel carbinol-containing polyimides capable of self-crosslinking at low temperatures are prepared by reacting a molar excess of selected 3,3',4,4'-benzhydrol tetracarboxylic acid compounds (the tetraacid, diester-diacid, or (dianhydride) with polyfunctional polyamines (e.g. 4,4'-methylenedianiline, 1,6-hexanediamine, etc.) in an inert organic solvent at about 100.degree.-150.degree. C. The molar ratio of tetracarboxylic acid compound to diamine must be between 2:1 and 9:8. The polyimides may be crosslinked at less than 200.degree. C. via a reaction between the carbinol group(s) and the end group(s) of the polyimide.Type: GrantFiled: September 26, 1983Date of Patent: December 18, 1984Inventor: Jules E. Schoenberg
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Patent number: 4485231Abstract: A class of relatively low molecular-weight oligomers containing at least one isoimide group and terminal groups capable of undergoing an addition polymerization reaction are provided. These oligomers are characterized by excellent solubility in common solvents and a melting temperature considerably lower than their cure temperature, thus enabling the oligomers to be formed into cured polymers more slowly and at lower temperatures, all without the evolution of deleterious gases. The oligomers of the present invention may be formed by reacting an aromatic dianhydride with an aromatic diamine, followed by reaction with a functional mono-amine. The resulting product is then dehydrated to form the isoimide-containing oligomer.Type: GrantFiled: September 26, 1983Date of Patent: November 27, 1984Assignee: Hughes Aircraft CompanyInventor: Abraham L. Landis