Carboxylic Acid Contains At Least Four Carboxylic Acid Groups Or Is A Derivative Of A Carboxylic Acid Containing At Least Four Carboxylic Groups Patents (Class 528/353)
  • Patent number: 4358562
    Abstract: Novel copolyimides and molding compositions are prepared from tetramethylcyclobutane-1,2,3,4-tetracarboxylic dianhydride and mixtures of diamines. Also glass and graphite filled polyimides are prepared. The polyimides are useful as engineering plastics.
    Type: Grant
    Filed: July 24, 1981
    Date of Patent: November 9, 1982
    Assignee: Standard Oil Company (Indiana)
    Inventors: Edward E. Paschke, Tayseer S. Nimry, Ellis K. Fields
  • Patent number: 4358579
    Abstract: Novel polyimides and molding compositions are prepared from tetramethylcyclobutane-1,2,3,4-tetracarboxylic dianhydride and diamines. Also glass and graphite filled polyimides are prepared. The polyimides are useful as engineering plastics.
    Type: Grant
    Filed: July 24, 1981
    Date of Patent: November 9, 1982
    Assignee: Standard Oil Company (Indiana)
    Inventors: Tayseer S. Nimry, Ellis K. Fields
  • Patent number: 4358581
    Abstract: A process is disclosed for manufacturing high molecular weight polyimide from a chilled solution which includes a polyamide acid prepolymer, a finishing component, and a converting system wherein, when the solution is heated, polyamide acid polymer is formed and converted to polyimide.
    Type: Grant
    Filed: December 5, 1980
    Date of Patent: November 9, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Richard F. Sutton, Jr.
  • Patent number: 4358580
    Abstract: Novel polyimides, copolyimides and molding compositions are prepared from novel dianhydrides such as tricyclo[6.4.0.0.sup.2,7 ] dodecane-3,6-diphenyl-1,8,4,5-tetracarboxylic acid dianhydride and tricyclo[6.4.0.0.sup.2,7 ] dodecane-1,8,4,5-tetracarboxylic acid dianhydride. The novel polyimides are useful as engineering plastics. The novel dianhydrides are useful for the preparation of the polyimides. Other dianhydrides can be mixed with our novel dianhydrides to make novel copolyimides useful as engineering plastics.
    Type: Grant
    Filed: August 19, 1981
    Date of Patent: November 9, 1982
    Assignee: Standard Oil Company (Indiana)
    Inventors: Tayseer S. Nimry, Ellis K. Fields
  • Patent number: 4353998
    Abstract: High density structural ("blocking") materials composed of a polyimide filled with glass microballoons. Structural components such as panels which have integral edgings and/or other parts made of the high density materials.
    Type: Grant
    Filed: September 28, 1981
    Date of Patent: October 12, 1982
    Assignee: International Harvester Company
    Inventors: John Gagliani, Raymond Lee
  • Patent number: 4352927
    Abstract: A method of improving the processability of rigid polymers, particularly of unprocessable rigid polymers, wherein the rigid polymer in melt or solution form is subjected to an apparent shear rate between relatively moving surfaces of at least 100 sec.sup.-1, particularly between 100 and 1000 sec.sup.-1. The method reduces the viscosity of the melt or solution and when the melt or solution is fabricated into shaped articles while the viscosity is so reduced the shaped articles have improved properties, particularly more uniform orientation when compared with products prepared by methods which do not include the pre-shearing step prior to fabrication.
    Type: Grant
    Filed: May 18, 1979
    Date of Patent: October 5, 1982
    Assignee: Imperial Chemical Industries Limited
    Inventors: Frederic N. Cogswell, Jiri G. Tomka
  • Patent number: 4346182
    Abstract: Terpolyimides prepared from tetracarboxylic acid esters and combinations of heterocyclic, aromatic, and aliphatic diamines and artifacts composed of those terpolymers. Precursors, and methods of converting them to the corresponding terpolymers.
    Type: Grant
    Filed: April 14, 1981
    Date of Patent: August 24, 1982
    Assignee: International Harvester Company
    Inventors: John Gagliani, Raymond Lee
  • Patent number: 4346212
    Abstract: This invention relates to thermally stable resins and provides such a resin made from cheaply available coal-derived materials, whereas presently available resins are made from increasingly expensive oil-derived materials.The resin comprises the condensation product of a reaction between an aromatic diamine and a phenanthrene-formaldehyde reaction product, which product has been oxidized to produce keto groups bridging the phenanthrene moieties and carboxy groups. The condensation product is a poly-(amide-imide).The invention also includes a method of making the resin and varnishes containing the resin.The resin will find use for instance as a high temperature insulator or in glass or asbestos laminates in compressor blades.
    Type: Grant
    Filed: July 31, 1980
    Date of Patent: August 24, 1982
    Assignee: Coal Industry (Patents) Limited
    Inventors: Joseph G. Robinson, David I. Barnes, Angela M. Carswell
  • Patent number: 4338430
    Abstract: The present invention provides an improvement in a process for preparing polyimide compositions from a mixture of monomers by the application of heat in two stages. The improvement comprises incorporating a cyclic peroxyketal catalyst, such as 3,6,6,9,9,-pentamethyl-3-(ethylacetate)-1,2,4,5-tetraoxycyclononane, into the monomer mixture prior to reaction.
    Type: Grant
    Filed: April 18, 1980
    Date of Patent: July 6, 1982
    Assignee: Celanese Corporation
    Inventor: Robert Edelman
  • Patent number: 4336175
    Abstract: Stoichiometrically imbalanced solutions of 6FTA and aromatic diamine can be used to prepare laminates and bonded articles having a broad temperature range for consolidation.
    Type: Grant
    Filed: October 1, 1980
    Date of Patent: June 22, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Hugh H. Gibbs
  • Patent number: 4332586
    Abstract: Alkylated glyoxal/cyclic urea condensates are excellent formaldehyde-free crosslinking resins for textile fabrics.
    Type: Grant
    Filed: May 15, 1981
    Date of Patent: June 1, 1982
    Assignee: Sun Chemical Corporation
    Inventor: Bernard F. North
  • Patent number: 4332929
    Abstract: Copolymers of etherimides and amides have been found to be useful in the coating and molding arts.
    Type: Grant
    Filed: March 16, 1981
    Date of Patent: June 1, 1982
    Assignee: General Electric Company
    Inventors: Fred F. Holub, Gary A. Mellinger
  • Patent number: 4332656
    Abstract: Copolymide foams derived from a diester of 3,3',4,4'-benzophenonetetracarboxylic acid, an aromatic diamine, and a heterocyclic diamine. A molar concentration of the heterocyclic diamine approaching but not exceeding 0.42 is employed. This results in a flexible foam with a homogeneous cellular structure and a reduced compression set loss.
    Type: Grant
    Filed: April 10, 1981
    Date of Patent: June 1, 1982
    Assignee: International Harvester Company
    Inventors: John Gagliani, Raymond Lee, Usman A. K. Sorathia
  • Patent number: 4332708
    Abstract: Wire coating formulations are provided by heating a mixture of aromatic dianhydride, water and a monoalkyl glycol ether, followed by the addition of organic diamine. The resulting mixture is a stable wire coating enamel capable of forming flexible wire enamels upon cure.
    Type: Grant
    Filed: February 27, 1980
    Date of Patent: June 1, 1982
    Assignee: General Electric Company
    Inventors: Edith M. Boldebuck, Eugene G. Banucci
  • Patent number: 4331799
    Abstract: Copolymers of etherimides and amideimides have been found to be useful in the coating and molding arts.
    Type: Grant
    Filed: March 2, 1981
    Date of Patent: May 25, 1982
    Assignee: General Electric Company
    Inventors: Fred F. Holub, Gary A. Mellinger
  • Patent number: 4330658
    Abstract: Curable resin compositions comprising a mixture and/or a preliminary reaction product of (a) at least one cyanate compound selected from the group consisting of polyfunctional cyanate esters, prepolymers of said cyanate esters, coprepolymers of said cyanate esters and an amine and mixtures thereof and (b) a polyamideimide resin and optionally (c) at least one maleimide compound selected from the group consisting of polyfunctional maleimides, prepolymers of said maleimides, coprepolymers of said maleimides and an amine and mixtures thereof are disclosed.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: May 18, 1982
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Nobuyuki Ikeguchi, Hidenori Kimbara
  • Patent number: 4321319
    Abstract: There is described photosensitive polymer composition and a polyimide film-coated material made by applying the composition to a support, irradiating with ultraviolet and thereafter heating. The photosensitive polymer composition is prepared by adding a sensitizer to a photosensitive polyamide acid intermediate solution which is obtained by reacting in an inert solvent a first compound comprising 100 to 5% by weight of a photosensitive group-containing diamine and 0 to 95% by weight of a diamine having no photosensitive group, with a second compound comprising at least one compound selected from a tetracarboxylic acid dianhydride and a tricarboxylic acid anhydride monohalide.
    Type: Grant
    Filed: May 22, 1980
    Date of Patent: March 23, 1982
    Assignee: Hitachi, Ltd.
    Inventors: Fusaji Shoji, Issei Takemoto, Hitoshi Yokono, Tokio Isogai
  • Patent number: 4321198
    Abstract: Novel compositions comprising acetylenic polyhemi-amic acid compositions and processes for their preparation are disclosed herein. These new compositions are primarily derivatives of anhydride-terminated aromatic polyimides from which they are prepared by amidation to provide acetylenic amide groups having terminal .dbd.C.tbd.CH groups as hemi-amic acid groups of their derivatives. These new compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures to crosslinked, insoluble, infusible polymers without by-product formation thereby extending greatly the applications for which the aromatic polyimides can be employed. Also included are monomeric compounds containing acetylenic amide groups derived from monomeric tetracarboxylic dianhydrides. These are particularly useful as crosslinking agents.
    Type: Grant
    Filed: January 25, 1980
    Date of Patent: March 23, 1982
    Assignee: Plastics Engineering Company
    Inventors: Gaetano F. D'Alelio, Phillip A. Waitkus
  • Patent number: 4320217
    Abstract: Novel compositions comprising polymerization products of polyimide derivatives having terminal acetylenic amide groups and processes for their preparation are disclosed herein. These new compositions are primarily polymers of derivatives of anhydride-terminated aromatic polyimides from which these derivatives are prepared by amidation to provide acetylenic amide groups having terminal --C.tbd.CH groups as hemi-amic acid groups or their derivatives. These derivative compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures and in accordance with the practice of this invention to crosslinked, insoluble, infusible polymers without by-product formation thereby extending greatly the applications for which the aromatic polyimides can be employed. Also included are polymers from monomeric compounds containing acetylenic amide groups derived from monomeric tetracarboxylic dianhydrides.
    Type: Grant
    Filed: January 25, 1980
    Date of Patent: March 16, 1982
    Assignee: Plastics Engineering Company
    Inventors: Gaetano F. D'Alelio, Phillip A. Waitkus
  • Patent number: 4319000
    Abstract: Closed cell polyimide foams. Methods of making such foams from precursors derived from a benzophenonetetracarboxylic acid diester and a mixture of diamines in which the precursor is molded to shape and cured, hydrated, and heated until a porous, closed cell structure develops.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: March 9, 1982
    Assignee: International Harvester Company
    Inventors: John Gagliani, John V. Long
  • Patent number: 4316844
    Abstract: Novel compositions comprising unsaturated polyhemi-amic acid compositions and processes for their preparation are disclosed herein. These new compositions are primarily derivatives of anhydride-terminated aromatic polyimides from which they are prepared by amidation to provide unsaturated amide groups having terminal --CH.dbd.CH.sub.2 groups as hemi-amic acid groups or their derivatives. These new compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures to crosslinked, insoluble, infusible polymers without by-product formation thereby extending greatly the applications for which the aromatic polyimides can be employed. Also included are monomeric compounds containing unsaturated amide groups derived from monomeric tetracarboxylic dianhydrides. These are particularly useful as crosslinking agents.
    Type: Grant
    Filed: January 25, 1980
    Date of Patent: February 23, 1982
    Assignee: Plastics Engineering Company
    Inventors: Phillip A. Waitkus, Gaetano F. D'Alelio
  • Patent number: 4316845
    Abstract: Novel compositions comprising acetylenic polyimide-polyamides and processes for their preparation are disclosed herein. These new compositions are primarily derivatives of anhydride-terminated aromatic polyimides from which they are prepared by amidation to provide acetylenic amide groups having terminal --C.dbd.CH groups. These new compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures to crosslinked, insoluble, infusible polymers without by-product formation thereby extending greatly the applications for which the aromatic polyimides can be employed. Also included are monomeric compounds containing acetylenic amide groups derived from monomeric tetracarboxylic dianhydrides. These are particularly useful as crosslinking agents.
    Type: Grant
    Filed: January 25, 1980
    Date of Patent: February 23, 1982
    Assignee: Plastics Engineering Company
    Inventors: Gaetano F. D'Alelio, Phillip A. Waitkus
  • Patent number: 4316843
    Abstract: Novel compositions comprising unsaturated polyimide-polyamides and processes for their preparation are disclosed herein. These new compositions are primarily derivatives of anhydride-terminated aromatic polyimides from which they are prepared by amidation to provide unsaturated amide groups having terminal --CH.dbd.CH.sub.2 groups. These new compositions are more tractable than the original anhydride-terminated polyimides and can be converted at appropriate lower temperatures to crosslinked, insoluble, infusible polymers without by-product formation thereby extending greatly the applications for which the aromatic polyimides can be employed. Also included are monomeric compounds containing unsaturated amide groups derived from monomeric tetracarboxylic dianhydrides. These are particularly useful as crosslinking agents.
    Type: Grant
    Filed: January 25, 1980
    Date of Patent: February 23, 1982
    Assignee: Plastics Engineering Company
    Inventors: Phillip A. Waitkus, Gaetano F. D'Alelio
  • Patent number: 4315077
    Abstract: Terpolyimides prepared from tetracarboxylic acid esters and combinations of heterocyclic, aromatic, and aliphatic diamines and artifacts composed of those terpolymers. Precursors, and methods of converting them to the corresponding terpolymers.
    Type: Grant
    Filed: May 27, 1981
    Date of Patent: February 9, 1982
    Assignee: International Harvester Company
    Inventors: John Gagliani, Raymond Lee
  • Patent number: 4315076
    Abstract: Terpolyimides prepared from tetracarboxylic acid esters and combinations of heterocyclic, aromatic, and aliphatic diamines and artifacts composed of those terpolymers. Precursors, and methods of converting them to the corresponding terpolymers.
    Type: Grant
    Filed: April 14, 1981
    Date of Patent: February 9, 1982
    Assignee: International Harvester Company
    Inventors: John Gagliani, Raymond Lee
  • Patent number: 4315080
    Abstract: Terpolyimides prepared from tetracarboxylic acid esters and combinations of heterocyclic, aromatic, and aliphatic diamines and artifacts composed of those terpolymers. Precursors, and methods of converting them to the corresponding terpolymers.
    Type: Grant
    Filed: May 27, 1981
    Date of Patent: February 9, 1982
    Assignee: International Harvester Company
    Inventors: John Gagliani, Raymond Lee
  • Patent number: 4313870
    Abstract: In a method producing a polycondensate by bulk polycondensation of a monomer (or a reactant mixture) which is a fluid at the polycondensation temperature, an improvement which comprises carrying out the polycondensation until substantially the whole polycondensate becomes a solid polydispersion while continually applying a shearing force sufficient for maintaining the polycondensation system in polydispersed state at a temperature of below the sintering of the produced polycondensate but sufficiently high for allowing the polycondensation to proceed substantially.
    Type: Grant
    Filed: September 5, 1978
    Date of Patent: February 2, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shozaburo Imai, Haruo Suzuki, Kuniaki Asai, Katsuji Ueno
  • Patent number: 4307220
    Abstract: A process for purifying an acetylene-terminated polyimide oligomer containing residual solvent in which the oligomer is initially dissolved in the same solvent used as the reaction medium in its synthesis. After precipitating the oligomer from solution by mixing with an aqueous solution of potassium or sodium chloride, the precipitated oligomer is washed successively with a plurality of liquids of decreasing polarity to provide an oligomer free of residual solvent.
    Type: Grant
    Filed: December 5, 1979
    Date of Patent: December 22, 1981
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Michael A. Lucarelli, Lewellyn G. Picklesimer
  • Patent number: 4305796
    Abstract: Methods of converting essentially unpolymerized precursors into polyimides in which the precursors are exposed to microwave radiation. Preheating, thermal post-curing, and other techniques may be employed to promote the development of optimum properties; and reinforcements can be employed to impart strength and rigidity to the final product. Also disclosed are processes for making various composite artifacts in which non-polymeric precursors are converted to polyimides by using the techniques described above.
    Type: Grant
    Filed: September 12, 1980
    Date of Patent: December 15, 1981
    Assignee: International Harvester Company
    Inventors: John Gagliani, Raymond Lee, Anthony L. Wilcoxson
  • Patent number: 4303775
    Abstract: A group of heat curable resins are provided which have good physical properties, which properties are retained to a surprising degree after prolonged exposure to temperatures as high as 300.degree. C. The products are acetylene end-capped esterimides having the structure: ##STR1## where R is an arylene group or a group having the structure: ##STR2## where X is ##STR3## R.sub.1 is an alkyl group containing 1 or 2 carbon atoms and R.sub.2 is hydrogen or an alkyl group containing 1 or 2 carbon atoms; and where R' is a phenylene group.
    Type: Grant
    Filed: September 6, 1979
    Date of Patent: December 1, 1981
    Assignee: Gulf Oil Corporation
    Inventors: Wai Y. Chow, S. Paul Thackaberry
  • Patent number: 4299750
    Abstract: The products of the invention are partial acetylene end-capped oligomers which have the structure as shown in FIG. 3 in which terminal R" group is derived from a mixture consisting of about 14-40 mol % of an aromatic monoamine and the balance an acetylene substituted aromatic monoamine. The products are prepared from either of two (2) precursors. The first precursor has the structure shown in FIG. 2. The second precursor is a complex amine salt having the structure shown in FIG. 5.
    Type: Grant
    Filed: May 3, 1979
    Date of Patent: November 10, 1981
    Assignee: Gulf Oil Corporation
    Inventors: Patricia A. Antonoplos, William J. Heilman
  • Patent number: 4290936
    Abstract: A polyimide solution is prepared by a process wherein a tetracarboxylic acid ingredient containing at least about 80% by mole of 3,3',4,4'-biphenyltetracarboxylic acid or its functional derivative and an aromatic diamine ingredient containing at least about 50% by mole of 4,4'-diaminodiphenyl ether are polymerized at from about 100.degree. to 300.degree. C. in phenol or a halogenated phenolic compound; the amount of the acid and diamine ingredients being approximately equimolar to each other; whereby polymerization of the tetracarboxylic acid ingredient and the aromatic diamine ingredient is effected while being accompanied by imidation. Preferably, the polymerization accompanied by imidation is effected in a manner such that at least a second half of the polymerization is carried out in a closed reaction system. The resulting polyimide solution is suitable for making therefrom shaped articles, such as films, possessing excellent mechanical properties.
    Type: Grant
    Filed: November 8, 1979
    Date of Patent: September 22, 1981
    Assignee: UBE Industries, Ltd.
    Inventors: Yoshikazu Sasaki, Hiroshi Inoue, Ichiro Sasaki, Hiroshi Itatani, Mikito Kashima
  • Patent number: 4284461
    Abstract: A method for preparing an aluminum ion-filled polyimide adhesive wherein a meta-oriented aromatic diamine is reacted with an aromatic dianhydride and an aluminum compound in the presence of a water or lower alkanol miscible ether solvent to produce an intermediate polyamic acid; and thereafter converting the polyamic acid to the thermally stable, metal ion-filled polyimide by heating in the temperature range of 300.degree. C. to produce a flexible, high temperature adhesive.
    Type: Grant
    Filed: November 7, 1979
    Date of Patent: August 18, 1981
    Inventors: Robert A. Administrator of the National Aeronautics and Space Administration, with respect to an invention of Frosch, Anne K. St. Clair, Larry T. Taylor, Terry L. St. Clair
  • Patent number: 4276407
    Abstract: Improved diimide and polyimide oligomers containing phenylacetylene terminal groups have been produced which melt at low temperatures and are curable into useful laminating resins, molding compounds and matrix resins. These oligomers are analogous to diimides and polyimides made from conventional dianhydrides, such as benzophenonetetracarboxylic dianhydride or pyromellitic dianhydride.
    Type: Grant
    Filed: August 16, 1979
    Date of Patent: June 30, 1981
    Assignee: Hughes Aircraft Company
    Inventors: Norman Bilow, Abraham L. Landis
  • Patent number: 4273886
    Abstract: Polyimide foams derived from mixtures of aromatic diamines and partial esters of a benzophenonetetracarboxylic acid. The precursors are converted into polyimide foams by the application of heat; and the foams are then compressed, yielding dense, rigid, and structurally strong, intumescent materials.
    Type: Grant
    Filed: February 15, 1980
    Date of Patent: June 16, 1981
    Assignee: International Harvester Company
    Inventor: John Gagliani
  • Patent number: 4271079
    Abstract: A novel compound, 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, of the following formula is provided. ##STR1## This novel tetracarboxylic acid dianhydride is useful as a curing agent for epoxy resins.
    Type: Grant
    Filed: September 5, 1979
    Date of Patent: June 2, 1981
    Assignee: Dainippon Ink & Chemicals, Inc.
    Inventors: Hiroshi Maeda, Nagao Ariga, Hiroshi Oikawa, Hidemitsu Tominaga
  • Patent number: 4271288
    Abstract: Novel polymeric materials are formed from dianhydride compounds of the formula ##STR1## wherein Ar, R' and R" are named substituents, and both x's are either zeros or ones.
    Type: Grant
    Filed: January 21, 1980
    Date of Patent: June 2, 1981
    Assignee: The Dow Chemical Company
    Inventor: Edmund P. Woo
  • Patent number: 4269968
    Abstract: Polyamic acid having greatly increased adhesive ability is prepared by compacting a solid aromatic dianhydride to reduct its surface area to weight ratio and reacting the compacted dianhydride with a solution of an organic diamine in an inert non-aqueous solvent.
    Type: Grant
    Filed: November 13, 1979
    Date of Patent: May 26, 1981
    Assignee: International Business Machines Corporation
    Inventors: John Duran, Leo Missel, Thomas O. Montelbano
  • Patent number: 4255483
    Abstract: Fire barrier composition particularly applicable as an acoustic panel-fire wall structure in aircraft, capable of withstanding a 2,000.degree. F. flame temperature, comprising incorporating a silica-containing material such as silicic acid or the reaction product of silicic acid and maleic anhydride, into a resin, particularly a polyimide resin. The resulting silica-containing resin, e.g. silicic acid-filled polyimide, is then applied to a substrate such as graphite fiber or glass cloth, to form a composite structure, which is then cured. The resulting cured composite when subjected to high temperature, e.g. a 2,000.degree. F. flame temperature, forms silicon carbide and/or silicon nitride, in situ, which stabilizes any char that forms.
    Type: Grant
    Filed: June 14, 1977
    Date of Patent: March 10, 1981
    Assignee: McDonnell Douglas Corporation
    Inventors: Norman R. Byrd, John K. Donahoe
  • Patent number: 4251417
    Abstract: The products of the invention are acetylene end-capped polyimide oligomers prepared from a dianhydride of an aromatic tetracarboxylic acid such as 3,3',4,4' benzophenonetetracarboxylic acid, an aromatic triamine, and an acetylene-substituted aromatic monoamine. The structure of the polyimide oligomers is shown in FIG. 3.
    Type: Grant
    Filed: April 25, 1979
    Date of Patent: February 17, 1981
    Assignee: Gulf Oil Corporation
    Inventors: Wai Y. Chow, William J. Heilman
  • Patent number: 4251418
    Abstract: The products of the invention are acetylene end-capped polyimide oligomers prepared from a dianhydride of an aromatic tetracarboxylic such as 3,3', 4,4'-benzophenonetetracarboxylic acid, an aromatic diamine, and a propargyl ester of an amino-substituted aromatic acid such as aminobenzoic acid. The structure of the polyimide oligomers is shown in FIG. 3.
    Type: Grant
    Filed: April 27, 1979
    Date of Patent: February 17, 1981
    Assignee: Gulf Oil Corporation
    Inventors: Wai Y. Chow, S. Paul Thackaberry
  • Patent number: 4251419
    Abstract: The products of the invention are vinyl end-capped oligomers which have the structure as shown in FIG. 3. The products are prepared from either of two (2) precursors. The first precursor is a compound which has the structure as shown in FIG. 2. The second precursor is a complex amine salt which has the structure shown in FIG. 5.
    Type: Grant
    Filed: April 5, 1979
    Date of Patent: February 17, 1981
    Assignee: Gulf Oil Corporation
    Inventors: William J. Heilman, Daniel J. Hurley
  • Patent number: 4251420
    Abstract: The products of the invention are end-capped polyimide oligomers prepared from a dianhydride of an aromatic tetracarboxylic acid such as 3,3'4,4'-benzophenonetetracarboxylic acid, an aromatic triamine, and a 1-(aminoaryl)-3-hydroxy-3-methyl-1-butyne. The structure of the polyimide oligomers is shown in FIG. 3.
    Type: Grant
    Filed: April 23, 1979
    Date of Patent: February 17, 1981
    Assignee: Gulf Oil Corporation
    Inventors: Patricia A. Antonoplos, William J. Heilman
  • Patent number: 4244853
    Abstract: A composition for making polyimide resin-reinforced fibers or fabric. The composition is of the type disclosed in U.S. Pat. No. 3,745,149 and includes a polyfunctional ester, a polyfunctional amine, and an end-capping agent. The composition is impregnated into fibers or fabric and heated to form prepreg material. The tack retention characteristics of this prepreg material are improved by incorporating into the composition a liquid olefinic material compatible with the other ingredients of the composition. The prepreg material is heated at a higher temperature to effect formation of the polyimide resin and the monomeric additive is incorporated in the polyimide polymer structure.
    Type: Grant
    Filed: April 6, 1979
    Date of Patent: January 13, 1981
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Tito T. Serafini, Peter Delvigs
  • Patent number: 4242437
    Abstract: A photosensitized polyamic acid film comprising polyamic acid and a photoinitiator, which is curable to a polyimide upon exposure to actinic radiation in the absence of externally applied heat.
    Type: Grant
    Filed: May 11, 1979
    Date of Patent: December 30, 1980
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Robert R. Rohloff
  • Patent number: 4241114
    Abstract: Polyimide foams derived from mixtures of aromatic diamines and partial esters of a benzophenonetetracarboxylic acid. The precursors are converted into polyimide foams by the application of heat; and the foams are then compressed, yielding dense, rigid, and structurally strong, intumescent materials.
    Type: Grant
    Filed: February 15, 1980
    Date of Patent: December 23, 1980
    Assignee: International Harvester Company
    Inventor: John Gagliani
  • Patent number: 4241193
    Abstract: Polyimide foams derived from mixtures of aromatic diamines and partial esters of a benzophenonetetracarboxylic acid. The precursors are converted into polyimide foams by the application of heat; and the foams are then compressed, yielding dense, rigid, and structurally strong, intumescent materials.
    Type: Grant
    Filed: August 21, 1978
    Date of Patent: December 23, 1980
    Assignee: International Harvester Company
    Inventor: John Gagliani
  • Patent number: 4238528
    Abstract: A protective layer composition, suitable for protecting metal electrodes on components and other microelectronic circuitry, comprises an organic thermoplastic polymeric material, an organic solvent or solvents, and a non-ionic fluorocarbon surfactant as a wetting/leveling/flow control agent. A typical formulation comprises an aromatic polymer which cures to form a polyamide-imide polymer, an organic solvent or a mixture of orangic solvents and a non-ionic fluorocarbon surfactant.
    Type: Grant
    Filed: October 2, 1979
    Date of Patent: December 9, 1980
    Assignee: International Business Machines Corporation
    Inventors: Raymond W. Angelo, Richard M. Poliak, John R. Susko
  • Patent number: 4238601
    Abstract: A bisorthodinitrile of the formula: ##STR1## wherein R' and R" are perfluorinated alkyls having from 1 to 4 carbon at, and the phenyl groups are attached at the para position. A polyphthalocyanine resin is prepared by heating one or more of these bisorthodinitriles at a temperature from about 260.degree. C. to about 295.degree. C. These resins are particularly useful in high-temperature structural composites used in high-temperature, moist or corrosive environments.
    Type: Grant
    Filed: June 25, 1979
    Date of Patent: December 9, 1980
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Teddy M. Keller, James R. Griffith
  • Patent number: RE30922
    Abstract: The products of the invention are vinyl end-capped oligomers which are prepared from 2,4-bis (p-aminobenzyl) aniline and a vinyl substituted aromatic monoamine, the principal component of which is the compound whose structure is shown in FIG. 3. The products are prepared from either of two (2) precursors. The first precursor is a compound whose structure is shown in FIG. 2 and which is prepared from 2,4-bis (p-aminobenzyl) aniline, a dianhydride of an aromatic tetracarboxylic acid such as 3,3'4,4'-benzophenonetetracarboxylic acid (BTDA) and a vinyl substituted aromatic monoamine, such as 3-aminophenyl-ethylene (APE). The second precursor is a complex amine salt having the structure shown in FIG. 6 and which is prepared from 2,4-bis-(p-aminobenzyl) aniline, a dialkyl ester of BTDA and APE.
    Type: Grant
    Filed: August 25, 1980
    Date of Patent: May 4, 1982
    Assignee: Gulf Oil Corporation
    Inventors: William J. Heilman, Daniel J. Hurley