Phosphorus- Or Sulfur-containing Reactant Patents (Class 528/352)
  • Patent number: 4822853
    Abstract: 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: Grant
    Filed: July 15, 1986
    Date of Patent: April 18, 1989
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Masakazu Uekita, Hiroshi Awaji
  • Patent number: 4808696
    Abstract: 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: Grant
    Filed: June 1, 1987
    Date of Patent: February 28, 1989
    Assignee: General Electric Company
    Inventors: Tohru Takekoshi, Patricia P. Anderson, Thomas L. Evans
  • Patent number: 4801682
    Abstract: 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: Grant
    Filed: May 27, 1986
    Date of Patent: January 31, 1989
    Assignee: United Technologies Corporation
    Inventor: Daniel A. Scola
  • Patent number: 4785074
    Abstract: 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: Grant
    Filed: June 22, 1987
    Date of Patent: November 15, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Josef Pfeifer
  • Patent number: 4783522
    Abstract: 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: Grant
    Filed: July 11, 1986
    Date of Patent: November 8, 1988
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Mitsutoshi Aritomi, Makoto Terauchi
  • Patent number: 4778859
    Abstract: 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: Grant
    Filed: April 28, 1986
    Date of Patent: October 18, 1988
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Hideo Ai, Akihiko Ikeda, Kan-ichi Yokota
  • Patent number: 4774317
    Abstract: 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: Grant
    Filed: October 20, 1986
    Date of Patent: September 27, 1988
    Assignee: General Electric Company
    Inventors: John W. Verbicky, Jr., Elbridge A. O'Neil
  • Patent number: 4772678
    Abstract: 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: Grant
    Filed: August 5, 1985
    Date of Patent: September 20, 1988
    Assignee: CommTech International Management Corporation
    Inventors: Joanne R. Sybert, James F. Wolfe, Paul D. Sybert, Blake Wilson
  • Patent number: 4760126
    Abstract: 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: Grant
    Filed: September 8, 1986
    Date of Patent: July 26, 1988
    Assignees: Hitachi, Ltd., Hitachi Chemical Co. Ltd.
    Inventors: Shunichi Numata, Koji Fujisaki, Noriyuki Kinjo
  • Patent number: 4755585
    Abstract: 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: Grant
    Filed: July 25, 1986
    Date of Patent: July 5, 1988
    Assignee: Amoco Corporation
    Inventors: Robert B. Hanson, Jeffrey D. Felberg, Gary T. Brooks
  • Patent number: 4749777
    Abstract: 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: Grant
    Filed: June 11, 1987
    Date of Patent: June 7, 1988
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Noriaki Kohtoh, Toyohiko Abe, Hiroyoshi Fukuro
  • Patent number: 4746720
    Abstract: 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: Grant
    Filed: October 20, 1986
    Date of Patent: May 24, 1988
    Assignee: General Electric Company
    Inventor: Donald R. Berdahl
  • Patent number: 4742150
    Abstract: 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: Grant
    Filed: September 25, 1986
    Date of Patent: May 3, 1988
    Assignee: General Electric Company
    Inventors: John W. Verbicky, Jr., Elbridge A. O'Neil, Mark J. Bausch
  • Patent number: 4742152
    Abstract: 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: Grant
    Filed: May 27, 1986
    Date of Patent: May 3, 1988
    Assignee: United Technologies Corporation
    Inventor: Daniel A. Scola
  • Patent number: 4736015
    Abstract: 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: Grant
    Filed: October 19, 1982
    Date of Patent: April 5, 1988
    Assignee: Institut Francais du Petrole
    Inventors: Guy Rabilloud, Michel Senneron, Choua Cohen, Paul Mariaggi, Bernard Sillion
  • Patent number: 4728697
    Abstract: 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: Grant
    Filed: September 27, 1985
    Date of Patent: March 1, 1988
    Assignee: General Electric Company
    Inventors: Donald A. Bolon, Thomas B. Gorczyca
  • Patent number: 4725642
    Abstract: 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: Grant
    Filed: April 29, 1985
    Date of Patent: February 16, 1988
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Thomas P. Gannett, Robert J. Kassal, Rolland S. Ro, Julius Uradnisheck
  • Patent number: 4724257
    Abstract: 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: Grant
    Filed: July 14, 1986
    Date of Patent: February 9, 1988
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Mitsutoshi Aritomi, Makoto Terauchi
  • Patent number: 4716216
    Abstract: 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: Grant
    Filed: November 19, 1986
    Date of Patent: December 29, 1987
    Assignee: General Electric Company
    Inventors: Tohru Takekoshi, Patricia P. Anderson
  • Patent number: 4703103
    Abstract: 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: Grant
    Filed: March 16, 1984
    Date of Patent: October 27, 1987
    Assignee: CommTech International
    Inventors: James F. Wolfe, Paul D. Sybert
  • Patent number: 4689391
    Abstract: 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: Grant
    Filed: December 21, 1984
    Date of Patent: August 25, 1987
    Assignee: General Electric Company
    Inventors: Edward N. Peters, Daniel W. Fox
  • Patent number: 4687836
    Abstract: 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: Grant
    Filed: October 10, 1985
    Date of Patent: August 18, 1987
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Akira Ibi, Takushi Sato, Akihiro Yamaguchi, Shigeru Takahashi, Shigeyuki Shishido, Shoji Tamai, Hisai Nakajima
  • Patent number: 4681928
    Abstract: 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: Grant
    Filed: June 1, 1984
    Date of Patent: July 21, 1987
    Assignee: M&T Chemicals Inc.
    Inventors: Abe Berger, Rohitkumar H. Vora
  • Patent number: 4680373
    Abstract: 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: Grant
    Filed: May 27, 1986
    Date of Patent: July 14, 1987
    Assignee: General Electric Company
    Inventors: Patrick E. Gallagher, Ronald A. Greenberg
  • Patent number: 4654415
    Abstract: 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: Grant
    Filed: March 27, 1985
    Date of Patent: March 31, 1987
    Assignee: Siemens Aktiengesellschaft
    Inventors: Hellmut Ahne, Eberhard Kuhn
  • Patent number: 4647616
    Abstract: 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: Grant
    Filed: July 15, 1985
    Date of Patent: March 3, 1987
    Assignee: The Dow Chemical Company
    Inventors: Loren L. Swearingen, Jimmy D. Earls, Randy J. LaTulip
  • Patent number: 4645823
    Abstract: 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: Grant
    Filed: September 10, 1985
    Date of Patent: February 24, 1987
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Hideo Ai, Akihiko Ikeda, Yoshio Matsuoka
  • Patent number: 4629777
    Abstract: 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: Grant
    Filed: May 10, 1984
    Date of Patent: December 16, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Josef Pfeifer
  • Patent number: 4625013
    Abstract: 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: Grant
    Filed: December 20, 1984
    Date of Patent: November 25, 1986
    Assignee: General Electric Company
    Inventors: Thomas L. Evans, Marsha M. Grade
  • Patent number: 4622285
    Abstract: 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: Grant
    Filed: March 27, 1985
    Date of Patent: November 11, 1986
    Assignee: Siemens Aktiengesellschaft
    Inventor: Hellmut Ahne
  • Patent number: 4613637
    Abstract: 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: Grant
    Filed: December 27, 1983
    Date of Patent: September 23, 1986
    Assignee: Hughes Aircraft Company
    Inventors: Abraham L. Landis, Arthur B. Naselow
  • Patent number: 4609712
    Abstract: 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: Grant
    Filed: June 18, 1984
    Date of Patent: September 2, 1986
    Assignee: General Electric Company
    Inventors: Thomas L. Evans, Marsha M. Grade
  • Patent number: 4599396
    Abstract: 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: Grant
    Filed: September 4, 1984
    Date of Patent: July 8, 1986
    Assignee: General Electric Company
    Inventors: Tohru Takekoshi, Patricia P. Anderson
  • Patent number: 4588804
    Abstract: 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: Grant
    Filed: May 4, 1984
    Date of Patent: May 13, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Michael Fryd
  • Patent number: 4588805
    Abstract: 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: Grant
    Filed: September 6, 1984
    Date of Patent: May 13, 1986
    Assignee: General Electric Company
    Inventor: Robert E. Williams, Jr.
  • Patent number: 4587324
    Abstract: 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: Grant
    Filed: August 16, 1984
    Date of Patent: May 6, 1986
    Assignee: The United States of America as represented by the Administrator, National Aeronautics and Space Administration
    Inventors: John A. Mikroyannidis, Demetrius A. Kourtides
  • Patent number: 4556697
    Abstract: 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: Grant
    Filed: July 25, 1983
    Date of Patent: December 3, 1985
    Assignee: The Standard Oil Company
    Inventors: Benedict S. Curatolo, Gerald P. Coffey
  • Patent number: 4552931
    Abstract: 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: Grant
    Filed: September 11, 1984
    Date of Patent: November 12, 1985
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Terry L. St. Clair, Harold D. Burks
  • Patent number: 4551522
    Abstract: 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: Grant
    Filed: April 26, 1985
    Date of Patent: November 5, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Michael Fryd, David L. Goff
  • Patent number: 4550156
    Abstract: 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: Grant
    Filed: October 26, 1984
    Date of Patent: October 29, 1985
    Assignee: General Electric Company
    Inventor: Patrick E. Gallagher
  • Patent number: 4536565
    Abstract: 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: Grant
    Filed: August 16, 1984
    Date of Patent: August 20, 1985
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: John A. Mikroyannidis
  • Patent number: 4536560
    Abstract: 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: Grant
    Filed: May 29, 1984
    Date of Patent: August 20, 1985
    Assignee: Standard Oil Company (Indiana)
    Inventors: Mark L. Winzenburg, Ellis K. Fields, Benjamin L. Shneider
  • Patent number: 4533693
    Abstract: 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: Grant
    Filed: September 15, 1983
    Date of Patent: August 6, 1985
    Assignee: SRI International
    Inventors: James F. Wolfe, Paul D. Sybert, Joanne R. Sybert
  • Patent number: 4530993
    Abstract: 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: Grant
    Filed: November 2, 1984
    Date of Patent: July 23, 1985
    Assignee: Director General of Agency of Industrial Science & Technology
    Inventors: Takuma Jinda, Toshikazu Matsuda, Masanori Sakamoto
  • Patent number: 4499252
    Abstract: 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: Grant
    Filed: March 28, 1984
    Date of Patent: February 12, 1985
    Assignee: Nitto Electric Industrial Co., Ltd.
    Inventors: Kazumasa Igarashi, Katsuhiko Yamaguchi, Munekazu Tanaka
  • Patent number: 4499260
    Abstract: 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: Grant
    Filed: November 10, 1982
    Date of Patent: February 12, 1985
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Bappalige N. Achar, George M. Fohlen, John A. Parker
  • Patent number: 4496711
    Abstract: 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: Grant
    Filed: September 26, 1983
    Date of Patent: January 29, 1985
    Assignee: Hughes Aircraft Company
    Inventor: Abraham L. Landis
  • Patent number: 4495342
    Abstract: 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: Grant
    Filed: September 26, 1983
    Date of Patent: January 22, 1985
    Assignee: Hughes Aircraft Company
    Inventor: Abraham L. Landis
  • Patent number: 4489185
    Abstract: 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: Grant
    Filed: September 26, 1983
    Date of Patent: December 18, 1984
    Inventor: Jules E. Schoenberg
  • Patent number: 4485231
    Abstract: 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: Grant
    Filed: September 26, 1983
    Date of Patent: November 27, 1984
    Assignee: Hughes Aircraft Company
    Inventor: Abraham L. Landis