Nitrogen Reactant Contains At Least Three Amino-nitrogen Atoms Bonded To One Or More Carbon Atoms Patents (Class 528/186)
  • Patent number: 10960359
    Abstract: Provided herein are methods of making asymmetric membranes comprising a first layer and a second layer. The methods include preparing a polymeric solution comprising one or more polymers, casting the polymeric solution to form a polymeric film, contacting the polymeric film with a solvent comprising a crosslinker under conditions to form a first layer on the top of the film, wherein the first layer is dense and solvent resistant, and contacting the polymeric film having the dense, solvent-resistant first layer with a non-solvent solution under conditions that form a porous second layer on the bottom of the film.
    Type: Grant
    Filed: February 3, 2017
    Date of Patent: March 30, 2021
    Assignee: KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY
    Inventors: Klaus-Viktor Peinemann, Jamaliah Hani Aburabie, Luis Francisco Villalobos Vazquez de la Parra
  • Publication number: 20140224124
    Abstract: Provided are cardo copolybenzimidazoles, a gas separation membrane using the same and a method for preparing the same. More particularly, provided are cardo copolybenzimidazoles obtained by introducing cardo groups and aromatic ether groups to a polybenzimidazole backbone, a gas separation membrane having significantly improved oxygen permeability by using the same, and a method for preparing the same. The cardo copolybenzimidazoles have improved solubility as compared to the polybenzimidazole polymers according to the related art, show excellent mechanical properties while maintaining thermal stability so as to be formed into a film shape, and provide a gas separation membrane having significantly improved gas permeability, particularly, oxygen permeability.
    Type: Application
    Filed: May 13, 2013
    Publication date: August 14, 2014
    Applicant: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY
    Inventors: Hyoung-Juhn KIM, Jun Young HAN, Jong Hyun JANG, Eun Ae CHO, Jonghee HAN, Suk Woo NAM, Tae-Hoon LIM, Sung Pil YOON, Sung Jong YOO, Dirk HENKENSMEIER
  • Patent number: 8664348
    Abstract: New triaminophenol compositions and related compounds are disclosed, as are processes for their preparation and for the preparation of novel salts and diacid complexes from such compounds. Polymers prepared from these compositions can be made into high strength fiber, film, and tape and are useful in applications such as protective apparel, aircraft, automotive components, personal electronics, and sports equipment.
    Type: Grant
    Filed: December 21, 2010
    Date of Patent: March 4, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Rajiv Dhawan, Joachim C Ritter, Frederick K Mallon, Steven R Allen, David J Rodini, Roger K Siemionko
  • Patent number: 8580910
    Abstract: New triaminophenol compositions and related compounds are disclosed, as are processes for their preparation and for the preparation of novel salts and diacid complexes from such compounds. Polymers prepared from these compositions can be made into high strength fiber, film, and tape and are useful in applications such as protective apparel, aircraft, automotive components, personal electronics, and sports equipment.
    Type: Grant
    Filed: December 21, 2010
    Date of Patent: November 12, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Rajiv Dhawan, Annalisa Hargis, Joachim C Ritter
  • Publication number: 20130012679
    Abstract: New triaminophenol compositions and related compounds are disclosed, as are processes for their preparation and for the preparation of novel salts and diacid complexes from such compounds. Polymers prepared from these compositions can be made into high strength fiber, film, and tape and are useful in applications such as protective apparel, aircraft, automotive components, personal electronics, and sports equipment.
    Type: Application
    Filed: December 21, 2010
    Publication date: January 10, 2013
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: Rajiv Dhawan, Joachim C. Ritter, Frederick K. Mallon, Steven R. Allen, David J. Rodini, Roger K. Siamionko
  • Patent number: 8298375
    Abstract: The invention concerns a paper comprising (a) 40 to 70 parts by weight of polypyridobisimidazole fiber, polypyridobisimidazole pulp, or mixtures thereof and (b) 30 to 60 parts by weight of friction modifiers, structural resins, wet-strength resins, processing aids, fillers, and mixtures thereof; the parts by weight being based on the total amount of a) and b) in the paper.
    Type: Grant
    Filed: December 19, 2006
    Date of Patent: October 30, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Edmund A. Merriman, Achim Amma
  • Publication number: 20110275781
    Abstract: A polyimide represented by formula (6) is provided. The polyimide is fabricated by performing a polycondensation reaction with a amine compound shown in formula (4) and a dianhydride compound shown in formula (5) as monomers. In formulas (5) and (6), Ar represents aromatic group, and n represents a positive integer.
    Type: Application
    Filed: October 22, 2010
    Publication date: November 10, 2011
    Applicant: National Taiwan University of Science and Technology
    Inventor: Der-Jang Liaw
  • Patent number: 7652124
    Abstract: There are provided a rigid heterocyclic polymer comprising rigid recurring units such as units represented by the following formulae (a) and (b): wherein X is O, S or NH, a production process thereof, and fibers comprising the polymer.
    Type: Grant
    Filed: April 12, 2005
    Date of Patent: January 26, 2010
    Assignees: Teijin Limited, Teijin Techno Products Limited
    Inventors: Masayuki Chokai, Anton Peter De Weijer, Hiroaki Kuwahara, Shunichi Matsumura
  • Patent number: 7288603
    Abstract: An object of the present invention is to obtain a novel polymeric material capable of forming a solid polymer electrolyte excellent not only in processability, solvent resistance and durability/stability but also in ion conductivity by introducing sulfonic acid group or phosphonic acid group into a polybenzazole compound having excellent properties in view of heat resistance, solvent resistance, mechanical characteristics and the like. Means attaining the object of the present invention is a polybenzazole compound including an aromatic dicarboxylic acid bond unit having sulfonic acid group and/or phosphonic acid group and satisfying either a condition that inherent viscosity measured in concentrated sulfuric acid is in the range of 0.25 to 10 dl/g or a condition that inherent viscosity measured in a methanesulfonic acid solution is in the range of 0.1 to 50 dl/g.
    Type: Grant
    Filed: November 12, 2001
    Date of Patent: October 30, 2007
    Assignee: Toyo Boseki Kabushiki Kaisha
    Inventors: Yoshimitsu Sakaguchi, Kota Kitamura, Hiroaki Taguchi, Junko Nakao, Shiro Hamamoto, Hiroshi Tachimori, Satoshi Takase
  • Patent number: 7186454
    Abstract: A material for dielectric films is a polymerizable composition containing an organic solvent, and an adamantanepolycarboxylic acid derivative represented by following Formula (1): wherein X is hydrogen atom, a hydrocarbon group or R4; R1, R2, R3 and R4 and are each independently a protected or unprotected carboxyl group, etc.; and Y1, Y2, Y3 and Y4 are each independently a single bond or a bivalent aromatic cyclic group; and an aromatic polyamine derivative represented by following Formula (2): wherein Ring Z is a monocyclic or polycyclic aromatic ring; and R5, R6, R7 and R8 are each a substituent bound to Ring Z and are each independently a protected or unprotected amino group, etc., dissolved in the organic solvent.
    Type: Grant
    Filed: March 24, 2004
    Date of Patent: March 6, 2007
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Shinya Nagano, Jiichiro Hashimoto, Kiyoharu Tsutsumi, Yoshinori Funaki
  • Patent number: 6998464
    Abstract: The present invention relates to a method of preparing a solution of a polymer comprising recurring azole units, which comprises dissolving a sufficiently dried polymer comprising recurring azole units of the formula where the radicals Ar, Ar1 and Ar2 are tetravalent, divalent or trivalent aromatic or heteroaromatic groups and the radicals X, which are identical within a repeating unit, are each an oxygen atom, a sulfur atom or an amino group bearing a hydrogen atom, a group having 1–20 carbon atoms, preferably a branched or unbranched alkyl or alkoxy group, or an aryl group as further radical, in N,N-dimethylacetamide having a sufficiently low water content at a temperature above room temperature under an inert gas atmosphere, wherein a sufficiently dried polymer comprising recurring azole units of the formula (1) or (2) of which 90% by weight based on the total weight of the polymer comprising recurring azole units has a particle size of less than 1 mm is used.
    Type: Grant
    Filed: October 20, 2001
    Date of Patent: February 14, 2006
    Assignee: PEMEAS GmbH
    Inventors: Thomas Guth, Jürgen Pawlik, Reiner Tiefenstädter, Peter Brendel, Frauke Jordt
  • Patent number: 6911519
    Abstract: A series of low melting and low viscosity phenylethynyl end-capped polyimides (PETIs) possessed of long term thermal and mechanical stability useful as films, melt coatings, adhesives, matrix and RTM resins and particular as coatings for optical fibers and phenylethynyl end-capped bismides blended with PETIs are disclosed. Processes for their production including: 1) modification of PETI-5 oligomer by molecular weight adjustments by blending with reactive low melting phenylethynyl end-capped imide monomers, 2) modification of the PETI-5 backbone structure with other diamine components, and 3) modification of the PETI-5 backbone with bulky fluorinated groups are also disclosed.
    Type: Grant
    Filed: March 25, 2003
    Date of Patent: June 28, 2005
    Assignee: University of Connecticut
    Inventors: Daniel A. Scola, Christopher D. Simone
  • Patent number: 6818726
    Abstract: Polymers are prepared from A) 60 to 95 percent by weight of a mixture including A1) 20 to 70 percent by weight of hydroxyalkyl amino triazines and A2) 30 to 80 percent by weight of bis(hydroxyalkyl) amino triazines B) 5 to 40 percent by weight of polyfunctional compounds selected from one or more of B1) polyisocyanates and/or oligomeric polyesters or polyethers with isocyanate end groups, B2) aliphatic dicarboxylic acids, esters, chlorides or anhydrides, or aromatic polybasic acids, esters, chlorides or anhydrides, B3) aliphatic or aromatic diglycidal compounds or triglycidyl compounds, and, optionally, C) 1 to 20 percent by weight of aliphatic, cycloaliphatic or aromatic dihydroxy compounds, polyalkylene glycols and aliphatic aldehydes.
    Type: Grant
    Filed: July 25, 2002
    Date of Patent: November 16, 2004
    Assignee: Agrolinz Melamin GmbH
    Inventors: Manfred Rätzsch, Martin Burger, Manfred Arnold, Willy Frank
  • Patent number: 6657016
    Abstract: A polyester resin composition comprising 50 equivalents/ton or more of an aromatic ring in the resin and at least one thermosetting resin selected from the group consisting of melamine resin, urea resin, benzoguanamine resin and phenol resin. The aromatic ring in the polyester resin has a phenolic hydroxyl group and at least one of ortho-position and para-position of the aromatic ring to the phenolic hydroxyl group is a hydrogen atom. The resin composition has excellent toughness at ambient temperature and heat resistance.
    Type: Grant
    Filed: March 14, 2002
    Date of Patent: December 2, 2003
    Assignee: Toyo Boseki Kabushiki Kaisha
    Inventor: Takeshi Yatsuka
  • Patent number: 6156874
    Abstract: Rod-like aromatic heterocyclic polymers having repeating units of the formula --(--Q--Ar--).sub.m --(--Q--Ph--).sub.n)-- where Q is ##STR1## X is --O--, --S--, or --NH--; m is 0.05 to 1.0; n is 1.0-m; Ph is 1,4-phenylene; Ar is ##STR2## R.sub.1 and R.sub.2 are the same and are either H or CH.sub.3 ; and R.sub.3 and R.sub.4 are CH.sub.3.
    Type: Grant
    Filed: January 27, 1999
    Date of Patent: December 5, 2000
    Assignee: Georgia Tech Research Corp.
    Inventors: Xiaodong Hu, Satish Kumar, Malcolm B. Polk
  • Patent number: 5932688
    Abstract: An improved polybenzimidazole wherein the total concentration of metals other than alkali metal and alkaline earth metals is 10 ppm or less. The resulting polybenzimidazole is industrially useable in parts or components of apparatus for the manufacture of semiconductors and display devices.
    Type: Grant
    Filed: January 14, 1997
    Date of Patent: August 3, 1999
    Assignee: Hoechst Japan Limited
    Inventor: Makoto Murata
  • Patent number: 5907025
    Abstract: Esterification reactions conducted in the presence of Lewis acids, including the reactions between aromatic carboxylic acids and alcohols and between epoxides and carboxylic acids, may be conducted with the use as the catalyst of a hexaalkylguanidinium or .alpha.,.omega.-bis(pentaalkylguanidinium)alkane salt such as hexaethyiguanidinium chloride or bromide.
    Type: Grant
    Filed: May 27, 1997
    Date of Patent: May 25, 1999
    Assignee: General Electric Company
    Inventor: Daniel Joseph Brunelle
  • Patent number: 5902876
    Abstract: Improved process for producing a polybenzimidazole compound in solution by dissolving a fully dried polybenzimidazole of the following general formula (1) or (2) in N,N-dimethylacetamide of a sufficiently reduced water content at an elevated temperature of 260.degree. C. or higher in an inert gas atmosphere and a solution of the polybenzimidazole compound produced by the process. The solution remains useful for an extended time without using metal salts or any other stabilizers: ##STR1## where R.sup.1, R.sup.2 and R.sup.5 are tetra-, di- and trivalent aromatic groups, respectively; R.sup.3, R.sup.4 and R.sup.6 are each independently a hydrogen atom, an alkyl group or an aryl group; n is an integer of 2 or more.
    Type: Grant
    Filed: June 18, 1997
    Date of Patent: May 11, 1999
    Assignee: Hoechst Japan Limited
    Inventors: Makoto Murata, Toru Nakamura
  • Patent number: 5708127
    Abstract: The invention relates to a PMR type resin which comprises a mixture of:(a) nadic acid of Formula (Ia) or a derivative thereof ##STR1## (b) a diaminobisimide of Formula (Ib) ##STR2## (c) an aromatic tetracarboxylic acid of Formula (Ic) or a derivative thereof ##STR3## the components (a), (b) and (c) being present in the approximate molar proportions of 2:n:n-1 respectively.
    Type: Grant
    Filed: July 21, 1995
    Date of Patent: January 13, 1998
    Assignee: Commonwealth Scientific and Industrial Research Organisation
    Inventors: Jonathan Howard Hodgkin, Robert Eibl
  • Patent number: 5674969
    Abstract: A rigid rod polymer in which at least 50% of the recurring groups correspond to the formula; ##STR1## Included in the invention are processes for preparation of the above rigid rod polymer and using such polymer as well as compositions employing the above rigid rod polymer.
    Type: Grant
    Filed: October 27, 1995
    Date of Patent: October 7, 1997
    Assignee: Akzo Nobel NV
    Inventors: Doetze Jakob Sikkema, Vadim Leonidovich Lishinsky
  • Patent number: 5665855
    Abstract: Disclosed are polymers and copolymers containing at least one repeating unit of the formula ##STR1## in which X is O or NH; R is a single bond or a hydrocarbon chain; R' is a hydrocarbon chain containing one or two carbon atoms, and P is the residue of an oligomer HX--P--XH whose solution viscosity determined in meta-cresol at 30.degree. C. at concentrations of 0.5 g/dl is lower than 0.50 dl/g.sup.-1. Also disclosed is a process for obtaining the polymers and copolymers.
    Type: Grant
    Filed: July 23, 1993
    Date of Patent: September 9, 1997
    Assignee: Elf Atochem S.A.
    Inventors: Margarita Acevedo, Alain Fradet, Didier Judas
  • Patent number: 5633337
    Abstract: A polymer having repeating units of the formula: ##STR1## wherein Q is ##STR2## wherein X is --NH--, --S-- or --O--. A copolymer having repeating units of the formula: ##STR3## wherein x has a value of 0.01 to 0.99 and Q is ##STR4## wherein X is --NH--, --S-- or --O--.
    Type: Grant
    Filed: February 23, 1996
    Date of Patent: May 27, 1997
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Loon-Seng Tan, Kasturi R. Srinivasan
  • Patent number: 5606012
    Abstract: Polymeric polyetheramidoamine hydrogel materials, which are capable of complexing heparin in physiological conditions are herein described. Said materials are useful in the manufacturing of medical devices.
    Type: Grant
    Filed: November 22, 1994
    Date of Patent: February 25, 1997
    Assignee: Societa' Consortile Ricerche Angelini S.p.A.
    Inventors: Maria C. Tanzi, Gianfranco Palumbo
  • Patent number: 5602226
    Abstract: The yield of fully substituted, multidimensional aromatic hubs in the condensation of hydroxyl and acid halide functionalities is improved by adding a thallium catalyst, such as thallium ethoxide (T1-OC.sub.2 H.sub.5), in the solvent.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: February 11, 1997
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard, Ronald R. Stephenson
  • Patent number: 5594089
    Abstract: Thermomechanical and thermo-oxidative stabilities in heterocycle or heterocycle sulfone resin composites are improved by forming four crosslinks at each addition polymerization site in the backbone of the resin using crosslinking functionalities.
    Type: Grant
    Filed: October 21, 1994
    Date of Patent: January 14, 1997
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowtiz, Clyde H. Sheppard
  • Patent number: 5554715
    Abstract: Novel poly(N-arylenebenzimidazole)s (PNABls) are prepared by the aromatic nucleophilic displacement reaction of novel di(hydroxyphenyl-N-arylene benzimidazole) monomers with activated aromatic dihalides or activated aromatic dinitro compounds. The polymerizations are carried out in polar aprotic solvents such as N-methyl-2-pyrrolidinone or N,N-dimethylacetamide using alkali metal bases such as potassium carbonate at elevated temperatures under nitrogen. The di(hydroxyphenyl-N-arylenebenzimidazole) monomers are synthesized by reacting phenyl-4-hydroxybenzoate with bis(2-aminoanilino)arylenes in diphenylsulfone. Moderate molecular weight PNABIs of new chemical structures were prepared that exhibit a favorable combination of physical and mechanical properties. The use of the novel di(hydroxyphenyI-N-arylenebenzimidazole)s permits a more economical and easier way to prepare PNABIs than previous routes.
    Type: Grant
    Filed: January 17, 1995
    Date of Patent: September 10, 1996
    Assignee: The United States of America as represented by the Administrator of National Aeronautics and Space Administration
    Inventors: John W. Connell, Paul M. Hergenrother, Joseph G. Smith, Jr.
  • Patent number: 5498784
    Abstract: Alcohol-soluble aromatic heterocyclic copolymers having repeating units of the formula: ##STR1## wherein x has a value of 0.05 to 0.50 and y has a value of 1.0-x. These copolymers are useful in the preparation of organic/inorganic hybrid materials having transparency which comprise the sol-gel derived, hydrolytically condensed reaction product of a metal alkoxide of the formula M(OR).sub.w wherein R is a lower alkyl group, M is Si, Ti, Al or a mixture thereof, and w is the valence value of M, and the above copolymer.
    Type: Grant
    Filed: February 21, 1995
    Date of Patent: March 12, 1996
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Fred E. Arnold, Jom P. Chen
  • Patent number: 5492996
    Abstract: Alcohol-soluble aromatic heterocyclic polymers having repeating units of the formula: ##STR1## wherein X is --O-- or --S--, and R is selected from the group consisting of: ##STR2## and R' is selected from the group consisting of alkyl having 1 to 5 carbon atoms, alkaryl having 7 to 12 carbon atoms, aralkyl having 7 to 12 carbon atoms and substituted aromatic having 1 to 3 substituent groups.The alcohol-soluble polymers may be used for fabricating organic/inorganic hybrid composites with metal alkoxides M(OQ).sub.v, wherein M is Si, Ti, Al or the like and Q is a lower alkyl group. These polymers can also be used to coat materials or substrates which are susceptible to attack by highly corrosive acids. On drying, the ionic bond between the trialkylamine and the sulfo group is broken and the polymer reverts to the parent structure, thereby leaving a polymer coating. Yet further, the original amine can be exchanged with a less volatile amine or an amine having a desired functionality.
    Type: Grant
    Filed: February 21, 1995
    Date of Patent: February 20, 1996
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Thuy D. Dang, Jom P. Chen, Fred E. Arnold
  • Patent number: 5430123
    Abstract: The present invention provides new polymer compositions which contain novel substituted pyrazines or pyrazine derivatives ("NPD") which are functional and have useful application as a monomer (co-monomer) for a variety of high performance polymers such as polyester, polyarylate, polycarbonate, polyetherketones, epoxides, polyimides, polyamides, and polyamides-imides. These NPD have the general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are defined herein.
    Type: Grant
    Filed: November 1, 1994
    Date of Patent: July 4, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: George Kvakovszky, Richard Vicari, Olan S. Fruchey, Ahmed M. Tafesh, Charles B. Hilton
  • Patent number: 5422416
    Abstract: Described herein is a process for synthesizing polybenzazole polymers comprising: (a) contacting a bis(trihalomethyl) organic compound with a polyphosphoric acid under reaction conditions sufficient to convert at least about 25 mole percent of the trihalomethyl groups present to carboxylic acid or carboxylate groups, forming a reaction mixture thereby; and (b) contacting the reaction mixture with an aromatic compound having two o-amino-basic moieties under reaction conditions sufficient to form a polybenzazole polymer.
    Type: Grant
    Filed: June 28, 1994
    Date of Patent: June 6, 1995
    Assignee: The Dow Chemical Company
    Inventor: Ying H. So
  • Patent number: 5410012
    Abstract: Novel poly(N-arylenebenzimidazole)s (PNABIs) are prepared by the aromatic nucleophilic displacement reaction of novel di(hydroxyphenyl-N-arylene benzimidazole) monomers with activated aromatic dihalides or activated aromatic dinitro compounds. The polymerizations are carried out in polar aprotic solvents such as N-methyl-2-pyrrolidinone or N,N-dimethylacetamide using alkali metal bases such as potassium carbonate at elevated temperatures under nitrogen. The di(hydroxyphenyl-N-arylenebenzimidazole) monomers are synthesized by reacting phenyl-4-hydroxybenzoate with bis(2-aminoanilino)arylenes in diphenylsulfone. Moderate molecular weight PNABIs of new chemical structures were prepared that exhibit a favorable combination of physical and mechanical properties. The use of the novel di(hydroxyphenyl-N-arylenebenzimidazole)s permits a more economical and easier way to prepare PNABIs than previous routes.
    Type: Grant
    Filed: March 5, 1993
    Date of Patent: April 25, 1995
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: John W. Connell, Paul M. Hergenrother, Joseph G. Smith, Jr.
  • Patent number: 5393860
    Abstract: The present invention provides new polymer compositions which contain novel substituted pyrazines or pyrazine derivatives ("NPD") which are functional and have useful application as a monomer (co-monomer) for a variety of high performance polymers such as polyester, polyarylate, polycarbonate, polyetherketones, epoxides, polyimides, polyamides, and polyamides-imides. These NPD have the general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are defined herein.
    Type: Grant
    Filed: February 4, 1994
    Date of Patent: February 28, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: George Kvakovszky, Richard Vicari, Olan S. Fruchey, Ahmed M. Tafesh, Charles B. Hilton
  • Patent number: 5338828
    Abstract: Novel cyclic imino ether compositions containing one or more mesogenic moieties, when polymerized, result in products having improved properties.
    Type: Grant
    Filed: September 10, 1993
    Date of Patent: August 16, 1994
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5324808
    Abstract: In reactions to form PBZ polymers such as polybenzoxazole, monomers having an aromatic group bonded to a primary amine group and to a hydroxy, thio or amine group ortho to said primary amine group are contacted with monomers having an electron-deficient carbon group. In the present invention the electron deficient carbon group may be an alkali metal carboxylate group or a trihalomethyl group. Useful monomers include, for example, .alpha.,.alpha.,.alpha.,.alpha.',.alpha.',.alpha.'-hexachloroxylene and disodium terephthalate.
    Type: Grant
    Filed: June 30, 1993
    Date of Patent: June 28, 1994
    Assignee: The Dow Chemical Company
    Inventor: Ying H. So
  • Patent number: 5317078
    Abstract: Di(hydroxyphenyl)benzimidazole monomers were prepared from phenyl-4-hydroxybenzoate and aromatic bis(o-diamine)s. These monomers were used in the synthesis of soluble polybenzimidazoles. The reaction involved the aromatic nucleophilic displacement of various di(hydroxyphenyl)benzimidazole monomers with activated aromatic dihalides or activated aromatic dinitro compounds in the presence of an alkali metal base. These polymers exhibited lower glass transition temperatures, improved solubility, and better compression moldability over their commercial counterparts.
    Type: Grant
    Filed: October 30, 1991
    Date of Patent: May 31, 1994
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: John W. Connell, Paul M. Hergenrother, Joseph G. Smith
  • Patent number: 5312895
    Abstract: Para-ordered aromatic heterocyclic polymers having repeating units of the formula: ##STR1## wherein n has a value of 0.05 to 1.00 and Q is a benzobisazole of the formula ##STR2## wherein X is --S-- or --O--, are soluble in aprotic solvents.
    Type: Grant
    Filed: March 12, 1993
    Date of Patent: May 17, 1994
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Thuy D. Dang, Fred E. Arnold
  • Patent number: 5235023
    Abstract: In reactions to form PBZ polymers such as polybenzoxazole, monomers having an aromatic group bonded to a primary amine group and to a hydroxy, thio or amine group ortho to said primary amine group are contacted with monomers having an "electron-deficient carbon group." In the present invention the electron-deficient carbon group may be an alkali metal carboxylate group or a trihalomethyl group. Useful monomers include, for example, .alpha.,.alpha.,.alpha.,.alpha.',.alpha.',.alpha.',-hexachloroxylene and disodium terephthalate.
    Type: Grant
    Filed: June 6, 1991
    Date of Patent: August 10, 1993
    Assignee: The Dow Chemical Company
    Inventor: Ying H. So
  • Patent number: 5216110
    Abstract: Azole rings, such as oxazole and thiazole rings, can activate an aromatic ring bonded to a leaving group such as a halogen atom so that the aromatic ring will undergo aromatic nucleophilic substitution. The reaction is useful for making ethers, thioethers and amines containing azole rings. In particular, monomers having azole rings, activated aromatic rings with leaving groups and nucleophilic moieties can react under conditions of aromatic nucleophilic displacement to form non-rigid rod PBZ polymers. The non-rigid rod PBZ polymers can be used to form molecular composites with rigid rod PBZ polymers which molecular composites are not substantially phase separated.
    Type: Grant
    Filed: January 10, 1992
    Date of Patent: June 1, 1993
    Assignee: The Dow Chemical Company
    Inventors: Muthiah N. Inbasekaran, Michael J. Mullins
  • Patent number: 5200495
    Abstract: Rigid-rod aromatic heterocyclic polymers having repeating units of the formula: ##STR1## wherein Ba is a benzobisazole moiety of the formula: ##STR2## wherein X is --O--, --S-- or --NH.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: April 6, 1993
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Fred E. Arnold, Jom P. Chen
  • Patent number: 5194562
    Abstract: Azole rings, such as oxazole and thiazole rings, can activate an aromatic ring bonded to a leaving group such as a halogen atom so that the aromatic ring will undergo aromatic nucleophilic substitution. The reaction is useful for making ethers, thioethers and amines containing azole rings. In particular, monomers having azole rings, activated aromatic rings with leaving groups and nucleophilic moieties can react under conditions of aromatic nucleophilic displacement to form non-rigid rob PBZ polymers. The non-rigid rod PBZ polymers can be used to form molecular composites with rigid rod PBZ polymers which molecular composites are not substantially phase separated.
    Type: Grant
    Filed: January 10, 1992
    Date of Patent: March 16, 1993
    Assignee: The Dow Chemical Company
    Inventors: Muthiah N. Inbasekaran, Michael J. Mullins
  • Patent number: 5175232
    Abstract: Rigid-rod aromatic heterocyclic copolymers having repeating units of the formula: ##STR1## wherein n has a value of about 0.10 to 0.99, m is 1.0-n, Ar is a para-ordered divalent aromatic moiety, as defined hereinafter, and wherein Ba is a benzobisazole moiety of the formula: ##STR2## wherein X is --O--, --S-- or --NH. Ar can be any para-ordered divalent moiety such as, for example, 1,4-phenylene, 4,4'-biphenylene, 4,4"-terphenylene, and the like, as well as substituted divalent moieties, such as, for example: ##STR3## wherein R is Q or an alkyl group having 1 to 4 carbon atoms, wherein Q is ##STR4## wherein Z is --O-- or --S--; ##STR5## wherein R is as defined above, or ##STR6## wherein R.sup.1 and R.sup.3 are --H or -phenyl, R.sup.2 is --H or ##STR7## wherein Q is as defined above, and R.sup.4 is R.sup.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: December 29, 1992
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Fred E. Arnold, Jom P. Chen
  • Patent number: 5175234
    Abstract: Polyimide oligomers include (1) linear, monofunctional crosslinking oligomers prepared by condensing a monoanhydride end cap with a diamine that includes alternating ether and "Sulfone" (--SO.sub.2 --, --S--, --CO--, --(CF.sub.3).sub.2 C--, or --(CH.sub.3).sub.2 C--) linkages connecting alternating aromatic radicals and with a dianhydride (or dianhydride mixture), particularly the unsaturated, aliphatic dianhydride commonly known as MCTC; (2) linear, mono- or difunctional crosslinking oligomers prepared by condensing an amine end cap with a diamine and a dianhydride; and (3) multidimensional, crosslinking oligomers having an aromatic hub and at least three radiating arms connected to the hub, each arm including a crosslinking end cap at its distal end and at least one imide linkage.Blends, prepregs, and composites can be prepared from the oligomers.
    Type: Grant
    Filed: November 7, 1989
    Date of Patent: December 29, 1992
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 5136012
    Abstract: There are provided novel rod-like heterocyclic aromatic copolymers having peating groups of the formula: ##STR1## wherein n has a value of 0.01 to 0.50, wherein Ar is a para-oriented aromatic group and Q is an aromatic heterocyclic group of the formula: ##STR2## wherein Y is --S--, --O-- or --NR--, wherein R is selected from the group consisting of --H, alkyl having 1 to 4 carbon atoms, and aromatic having 1 or 2 aromatic rings.
    Type: Grant
    Filed: June 3, 1991
    Date of Patent: August 4, 1992
    Assignee: United States of America as Represented by the Secretary of the Air Force
    Inventors: Thuy D. Dang, Hoe H. Chuah, Loon S. Tan, Fred E. Arnold
  • Patent number: 5134219
    Abstract: The substituted polyheterocycles containing recurring structural units corresponding to the formula ##STR1## in which X is an oxygen atom, a sulfur atom or N-H, show good solubility in mixtures of methanesulfonic acid and methylene chloride or trifluoroacetic acid and methylene chloride. They may be used for the production of mixtures with thermoplastic polymers.
    Type: Grant
    Filed: November 26, 1990
    Date of Patent: July 28, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans R. Kricheldorf, Jurgen Engelhardt, Ralf Pakull, Volker Eckhardt, Ulrich Leyrer
  • Patent number: 5120825
    Abstract: The present invention provides for hybrid polybenzimidazole and polybenzimidazolone polymers which are characterized as containing both imidazole and imidazolone structural units in the polymer chain. These polymers are characterized as containing at least one recurring monomer unit containing the structure of the formula: ##STR1## wherein Ar is a tetravalent aromatic moiety derived from an aromatic tetraamine and Ar.sub.1 is a trivalent aromatic moiety derived from a trifunctional acid, an acid anhydride or amine-reactive derivatives thereof, said polymers further characterized by an inherent viscosity of at least about 0.01 dl/g measured as a 0.5% solution in N-methyl pyrrolidone at 25.degree. C.The polymers of this invention exhibit many of the advantageous properties of both polybenzimidazole and polybenzimidazolone polymers. They are characterized as being extremely resistant to chemical attack such as by solvents, acids and bases.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: June 9, 1992
    Assignee: Hoechst Celanese Corp.
    Inventors: Rohitkumar H. Vora, Paul N. Chen, Sr.
  • Patent number: 5116935
    Abstract: A preferred class of polyimide oligomers include (1) linear, difunctional crosslinking oligomers prepared by condensing an imidophenylamine end cap with a lower alkylene diamine or a polyaryldiamine such as 3,3'-phenoxyphenylsulfone diamine and with a dianhydride, particularly 4,4'-phenoxyphenylsulfone dianhydride; and (2) multidimensional, crosslinking, polyimide oligomers having an aromatic hub and at least two radiating arms connected to the hub, each arm including a crosslinking imidophenylamine end cap at its distal end and at least two imide linkages.Blends, prepregs, and composites can be prepared from the oligomers.
    Type: Grant
    Filed: May 18, 1989
    Date of Patent: May 26, 1992
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 5106940
    Abstract: There are provided novel rod-like heterocyclic aromatic polymers having repeating groups of the formula: ##STR1## wherein Y is --S--, --O-- or --NR--, R is -H, an alkyl group having 1 to 4 carbon atoms or an aromatic group having 1 or 2 aromatic rings, and the bullet symbol (.cndot.) indicates hydrogen bonding.
    Type: Grant
    Filed: June 3, 1991
    Date of Patent: April 21, 1992
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Thuy D. Dang, Hoe H. Chuah, Loon S. Tan, Fred E. Arnold
  • Patent number: 5104960
    Abstract: Azole rings, such as oxazole and thiazole rings, can activate an aromatic ring bonded to a leaving group such as a halogen atom so that the aromatic ring will undergo aromatic nucleophilic substitution. The reaction is useful for making ethers, thioethers and amines containing azole rings. In particular, monomers having azole rings, activated aromatic rings with leaving groups and nucleophilic moieties can react under conditions of aromatic nucleophilic displacement to form non-rigid rod PBZ polymers. The non-rigid rod PBZ polymers can be used to form molecular composites with rigid rod PBZ polymers which molecular composites are not substantially phase separated.
    Type: Grant
    Filed: February 22, 1989
    Date of Patent: April 14, 1992
    Assignee: The Dow Chemical Company
    Inventors: Muthiah N. Inbasekaran, Michael J. Mullins
  • Patent number: 5098988
    Abstract: There are provided para-ordered aromatic heterocyclic copolymers having repeating groups of the following formulas: ##STR1## wherein a, b, c, d, and e are positive integers, each representing an average number of the respective different recurring units present in the repeating group, m and n are 1 or 2, R and R' are alkyl groups having 1 to 4 carbon atoms, and Q is a benzobisazole group of the formula: ##STR2## wherein Y is --O--, --S--, or --NH--. In the copolymers wherein m or n is 2, the R or R' groups can be the same or different. In copolymer I, the ratio a:b can be about 1:1 to 99:1. In copolymer II, the ratio c:(d+e) can be about 1:1 to 99:1, and the ratio d:e can be about 1:99 to 99:1.
    Type: Grant
    Filed: November 30, 1990
    Date of Patent: March 24, 1992
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Tsu-Tzu Tsai, Fred E. Arnold
  • Patent number: 5098987
    Abstract: There are provided crosslinkable, para-ordered aromatic heterocyclic polymers having repeating groups of the following formula ##STR1## wherein Y is --O--, --S--, or --NH--, n is 1 or 2, and R is an alkyl group having 1 to 4 carbon atoms. In polymers having two pendant R groups, the R groups can be the same or different.
    Type: Grant
    Filed: November 30, 1990
    Date of Patent: March 24, 1992
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Tsu-Tzu Tsai, Fred E. Arnold