Phenolic Reactant Contains A Nitrogen Atom Patents (Class 528/210)
  • Patent number: 5968417
    Abstract: The invention provides conductive compositions of matter, as well as methods for the preparation of the conductive compositions of matter, solutions comprising the conductive compositions of matter, and methods of preparing fibers or fabrics having improved anti-static properties employing the conductive compositions of matter.
    Type: Grant
    Filed: March 3, 1998
    Date of Patent: October 19, 1999
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Tito Viswanathan
  • Patent number: 5968416
    Abstract: Optical quality transparent conductors such as bodies, films and coatings formed from substituted and unsubstituted polyanilines in nonconductive substrates such as polymers or polymer plus solvents with protonic acid are disclosed as are methods of forming such conductors from fluid forms of the polyaniline/substrate/acid mixtures.
    Type: Grant
    Filed: March 17, 1997
    Date of Patent: October 19, 1999
    Assignee: Uniax Corporation
    Inventors: Paul Smith, Alan J. Heeger, Yong Cao
  • Patent number: 5962632
    Abstract: Deaggregated substituted and unsubstitued polyparaphenylenes, polyparaphenylevevinyles, polyanilines, polyazines, polythiophenes, poly-p-phenylene sulfides, polyfuranes, polypyrroles, polysclenopliene, polyacetylenes formed from soluble precursors and combinations thereof and copolymers thereof and methods of fabrication are described. The deaggregated polymer molecules when subsequently doped show higher electrical conductivity. Agents such as lithium chloride, m-cresol and nonylphenol are used to deaggregate the polymer molecules. The deaggregating agents can be added prior to or during doping the molecules.
    Type: Grant
    Filed: August 14, 1997
    Date of Patent: October 5, 1999
    Assignee: International Business Machines Corporation
    Inventors: Marie Angelopoulos, Bruce K. Furman
  • Patent number: 5959072
    Abstract: A wastewater-recyclable polymerization process for producing a polyaniline-based resin includes: feeding into a reactor an aniline monomer, an acid solution and an oxidizing agent to undergo polymerization so as to produce polyaniline resin particles; filtering the polyaniline resin particles from an acidic aqueous solution formed during the polymerization; neutralizing and drying the polyaniline resin particles to form a powder; recycling the acidic aqueous solution by mixing the acidic aqueous solution in the reactor with a fresh reactant feed which contains the aniline monomer, the acid solution and the oxidizing agent; and permitting the reactant feed to undergo polymerization in the presence of the recycled acidic aqueous solution at room temperature without cooling the reactor.
    Type: Grant
    Filed: January 26, 1998
    Date of Patent: September 28, 1999
    Assignee: Conpoly Technology Co., Ltd.
    Inventors: Ko-Shan Ho, Tar-Hwa Hsieh
  • Patent number: 5932144
    Abstract: A soluble aniline conducting polymer characterized in that said conductive polymer comprises as a repeating unit an alkoxyl group-substituted aminobenzenesulfonic acid, its alkali metal salts, ammonium salts and/or substituted ammonium salts, and is a solid having a weight average molecular weight of about 1900 or more at room temperature, a conductive composition and electric conductor comprising the same, and a method for producing a soluble aniline conducting polymer having a weight average molecular weight of 10,000 t 3,240,000 characterized by polymerizing at least one compound (1) selected from the group consisting of an acidic group-substituted aniline, its alkali metal salts, ammonium salts and substituted ammonium salts in a solution containing a basic compound (2) using an oxidizing agent.
    Type: Grant
    Filed: August 22, 1997
    Date of Patent: August 3, 1999
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Shigeru Shimizu, Takashi Saitoh, Masashi Uzawa, Yasuyuki Takayanagi
  • Patent number: 5919890
    Abstract: A method for producing polybenzazole, which comprises reacting a PBZ monomer salt with an AA-PBZ monomer or a BB-PBZ monomer in a non-oxidizing solvent having a dehydrating action to give an oligomer, and adding the AA-PBZ monomer or BB-PBZ monomer, which has not been subjected to the above reaction, to allow reaction with the oligomer, whereby to give a polymer having a desired polymerization degree. According to this method, the polymerization degree of the polymer to be obtained finally and of the polymer during production process can be easily controlled.
    Type: Grant
    Filed: April 30, 1997
    Date of Patent: July 6, 1999
    Assignee: Toyo Boseki Kabushiki Kaisha
    Inventors: Kiyoshi Hotta, Fuyuhiko Kubota, Yoshio Araki, Masakatsu Ohguchi
  • Patent number: 5895606
    Abstract: A conductive polymer composition comprises a conjugated double bond-bearing polymer and a composite dopant consisting essentially of an organic anion derived from an anionic surface active agent and an inorganic anion derived from a transition metal salt. A process for preparing the conductive polymer composition is also described wherein the polymerizable proceeds rapidly in coexistence of the organic anion and the inorganic anion. Addition of fine particle of an oxide is effective in film formation on substrates.
    Type: Grant
    Filed: February 16, 1996
    Date of Patent: April 20, 1999
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Yasuo Kudoh, Toshikuni Kojima, Kenji Akami
  • Patent number: 5886130
    Abstract: A new class of polyarylene co-polymers include repeating units comprising one or more arylene units having the general formula (--Ar--/--Y--).sub.n, where Y is a divalent group chosen from nil, --Z--, --Z--Ph--, and --Ph--Z--Ph--, where Z is a divalent group chosen from the group consisting of --O--, --S--, --NR--, --O(CO)--, --O(CO.sub.2)--,--(CO)NH(CO)--, --NR(CO)--, phthalimide, pyromellitimide, --CO--, --SO--, --SO.sub.2 --, --P(O)R--, --CH.sub.2 --, --CF.sub.2 --, and --CRR'--; Ph is phenylene (ortho, meta or para); and n is greater than 4. The co-polymers are useful as molding resins, and composite matrix resins, and where Ar is heteroarylene as ion exchange resins.
    Type: Grant
    Filed: November 2, 1995
    Date of Patent: March 23, 1999
    Assignee: Maxdem Incorporated
    Inventors: Mark S. Trimmer, Ying Wang, Matthew L. Marrocco III, Virgil J. Lee
  • Patent number: 5863465
    Abstract: Emulsion-polymerization of electrically conductive polyaniline salts is disclosed. The process comprises combining water, a water-solubilizing organic solvent, an organic acid that is soluble in the organic solvent, an aniline monomer, and a radical initiator. An organic phase forms which contains the polyaniline salt of the organic acid wherein the organic phase is separable from an aqueous phase. The polyaniline salt so formed is soluble in organic carrier solvents at a concentration of 25 w/w % or greater.
    Type: Grant
    Filed: February 16, 1996
    Date of Patent: January 26, 1999
    Assignee: Monsanto Company
    Inventor: Patrick J. Kinlen
  • Patent number: 5844069
    Abstract: The invention provides copolymers having magnetic properties, said copolymers containing aminoaromatic groups, and being based on a structural unit comprising:a first group of aminoaromatic compounds chosen from aniline derivatives and the corresponding iminoquinone forms; anda second group of substituted aminoaromatic compounds chosen from substituted amino compounds containing at least two condensed benzene rings, substituted polycyclic compounds containing at least one aniline structural unit in their structure, compounds derived from aniline and carrying a substituent bonded to the ring by means of an ethynylidene or paraphenylene link, and the corresponding iminoquinone compounds.
    Type: Grant
    Filed: December 29, 1994
    Date of Patent: December 1, 1998
    Assignee: Alcatel Alsthom Compagnie Generale D'Electricite
    Inventors: Stanislas Galaj, Alain Le Mehaute
  • Patent number: 5824414
    Abstract: Phenols are reacted with hydrogen peroxide in a solution comprising an organic solvent compatible with water, water, a peroxidase and a dispersing agent to obtain spherical polyphenol particles.
    Type: Grant
    Filed: April 17, 1996
    Date of Patent: October 20, 1998
    Assignees: Mitsui Chemicals, Inc., Shiro Kobayashi
    Inventors: Shiro Kobayashi, Hiroshi Uyama, Sunao Maeda, Shinichirou Tawaki
  • Patent number: 5804100
    Abstract: Deaggregated substituted and unsubstituted polyparaphenylenes, polyparaphenylevevinyles, polyanilines, polyazines, polythiophenes, poly-p-phenylene sulfides, polyfuranes, polypyrroles, polyselenophene, polyacetylenes formed from soluble precursors and combinations thereof and copolymers thereof and methods of fabrication are described. The deaggregated polymer molecules when subsequently doped show higher electrical conductivity. Agents such as lithium chloride, m-cresol and nonylphenol are used to deaggregate the polymer molecules. The deaggregating agents can be added prior to or during doping the molecules.
    Type: Grant
    Filed: January 9, 1995
    Date of Patent: September 8, 1998
    Assignee: International Business Machines Corporation
    Inventors: Marie Angelopoulos, Bruce K. Furman
  • Patent number: 5804649
    Abstract: The present invention discloses a water-soluble self-acid-doped polyaniline, and its sodium salt, which can be cast into free-standing films from their aqueous solutions. A process for preparing a water-soluble self-acid-doped polyaniline is also disclosed, which comprises reacting a polyaniline with a strong base to convert the amino nitrogen thereof to anionic nitrogen; reacting sultone with the anionic nitrogen to form a side chain alkanesulfonic acid group; doping with protonic acid to form precipitate; dissolving (undoping) the precipitate in an alkaline aqueous solution; removing excess alkali from the alkaline aqueous solution; and contacting the resulting aqueous solution with a H.sup.+ -type ion exchange resin. Moreover, an aqueous solution of the present water-soluble self-acid-doped PAn can be easily mixed with an additional water soluble polymer or polymer emulsion, which can then be cased into a polymer blend film having improved mechanical properties and coupling strength to a substrate.
    Type: Grant
    Filed: July 21, 1997
    Date of Patent: September 8, 1998
    Assignee: National Science Council
    Inventors: Show-An Chen, Gue-Wuu Hwang
  • Patent number: 5792830
    Abstract: Described is a process for preparing polyaniline polymer which includes contacting aniline monomers with (a) hydrogen peroxide, (b) at least one acid, including hydrogen chloride, hydrogen bromide, or a mixture thereof, and (c) a catalytic amount of at least one metal-containing compound or complex, under reaction conditions sufficient to form a polymerization reaction product containing a polyaniline polymer. It has been discovered that the processes described herein provide means to prepare polyaniline having a relatively high conductivity at a high degree of aniline monomer conversion using hydrogen peroxide as an oxidant.
    Type: Grant
    Filed: December 9, 1996
    Date of Patent: August 11, 1998
    Assignee: The Dow Chemical Company
    Inventors: Stephen A. Noding, Susan J. Babinec, Carey L. Scortichini
  • Patent number: 5786071
    Abstract: New polyquinoline polymers are provided, as well as new methods for preparing the polyquinoline polymers using a novel combination of monomers. The polyquinoline polymers comprise repeat units comprising at least one quinoline nucleus and at least one ether linkage and having as end groups either fluoro groups or hydroxy groups or a combination of fluoro and hydroxy groups. The polymers are formed by providing a monomer comprising two fluoro groups, where each such fluoro group is activated by a quinoline nucleus, a diol monomer provided in the form of its bis-oxide salt, or in the presence of a base capable of deprotonating the diol and reacting the difluoro and diol monomers together in a dipolar solvent to form the polyquinoline polymer.
    Type: Grant
    Filed: April 9, 1997
    Date of Patent: July 28, 1998
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Matthew L. Marrocco, III, Ying Wang
  • Patent number: 5780572
    Abstract: A method for increasing the conductivity of a composition of a polyaniline salt of an organic acid is disclosed. The method comprises contacting the composition with a polar organic solvent that is capable of solubilizing the organic acid without solubilizing the polyaniline salt. Also provided are coating compositions which can be prepared by the method.
    Type: Grant
    Filed: July 26, 1996
    Date of Patent: July 14, 1998
    Assignee: Monsanto Company
    Inventor: Charles R. Graham
  • Patent number: 5776374
    Abstract: The present invention relates to crosslinkable thermoplastic compositions comprising a plurality of crosslinkable moieties, capable of undergoing addition polymerization, incorporated by functionalization of the precursor poly(hydroxy ethers). The poly(hydroxy ethers) comprise recurring moieties derived from aromatic dihydroxy compounds. The crosslinkable polymeric compositions are crosslinked to obtain crosslinked thermoset polymeric compositions of the invention. The polymeric compositions of the inventions can be suitably used either as an active guiding layer, and/or as a NLO active upper and lower cladding layers in an electro-optic device. The polymeric compositions can also be used as non-NLO polymers for the upper and lower cladding layers, prior to orientation by the application of an electric field.
    Type: Grant
    Filed: November 7, 1995
    Date of Patent: July 7, 1998
    Assignee: The Dow Chemical Company
    Inventors: Mark D. Newsham, Michael N. Mang, Robert J. Gulotty, Jr., Dennis W. Smith, Jr.
  • Patent number: 5773568
    Abstract: Methods for preparing conductive polyaniline forms are provided in which the conductivity of the polyaniline form can be substantially increased by contacting the polyaniline form with a phenolic compound that acts as a secondary dopant for the polyaniline. Generally, a doped polyaniline solution is prepared in which the polyaniline is initially doped by a protonic acid and a doped polyaniline form is then prepared from this solution. The polyaniline form can then be contacted with the phenolic compound in either its vapor or liquid state, however it is preferred that the polyaniline form be maintained in either the gelatinous or solid state during the contacting step. The conductivity of the polyanine form can be raised by a factor of up to about 500-1000.
    Type: Grant
    Filed: April 15, 1996
    Date of Patent: June 30, 1998
    Assignee: The Trustees of the University of Pennsylvania
    Inventors: Alan G. MacDiarmid, You Nan Xia, Joanna M. Wiesinger
  • Patent number: 5772923
    Abstract: A solution which comprises: a non-polar organic solvent, such as an aliphatic hydrocarbon solvent, like hexane; polyaniline; and an effective amount of an amphiphilic phenol-containing reagent, which can be a monomeric compound or a phenol-containing polymer, for the solubilization of the polyaniline in the solvent. The alkyl substituent in the phenol-containing reagent, if monomeric, can contain from about six to about twelve carbon atoms, with a preferred solubilizer being dodecylphenol.
    Type: Grant
    Filed: October 29, 1996
    Date of Patent: June 30, 1998
    Inventor: Kalle M. J. Levon
  • Patent number: 5773179
    Abstract: Materials of formula (I) are provided, wherein X.sub.1 -X.sub.5 are independently selected from H, F, Cl, NO.sub.2, CF.sub.3, OR, R, SR, .paren open-st.CO-- or .paren open-st.CO-- where R is C.sub.1-15 branched or straight chain alkyl; provided that one of X.sub.1 -X.sub.5 is selected from .paren open-st.CO-- or .paren open-st.OC--; p is at least 2; W=single bond, phenyl, fluorinated phenyl, .dbd., .tbd., cyclohexyl, thiophene, CO, OC; T.sub.1, T.sub.2, T.sub.3, T.sub.4 are independently selected from H, F, Cl, NO.sub.2, CF.sub.3, OR, R, SR, where R is C.sub.1-15 branched or straight chain alkyl; g=0 or 1; X is selected from CO.sub.2 and OOC; n is selected from 1-5; m is selected from 1-20, Y is selected from O, S, CH.sub.2, CO.sub.2, OOC; Q is CH.sub.2 and when m is greater than 1 then non-adjacent CH.sub.
    Type: Grant
    Filed: October 22, 1997
    Date of Patent: June 30, 1998
    Assignee: The Secretary of State for Defence Defence Evaluation & Research Agency
    Inventors: Georg H. R. Mehl, John W. Goodby, David Lacey
  • Patent number: 5744125
    Abstract: Disclosed are cosmetic melanins of different colors produced by procedures involving oxidative polymerization of monomeric precursors of melanin and/or co-monomers that enhance substantivity or adherence of the melanins to the skin and hair. Also disclosed are methods for preparing cosmetic melanins and methods for using these compositions topically to produce a natural-appearing tan and to prevent damage to skin caused by UV exposure.
    Type: Grant
    Filed: February 23, 1995
    Date of Patent: April 28, 1998
    Assignee: Yale University
    Inventors: John M. Pawelek, James T. Platt
  • Patent number: 5728321
    Abstract: This invention relates to a conducting organic polymer formed by doping an organic polymer with a protonic acid having a dissociation constant value pKa of less than 4.8, wherein the organic polymer has, as the main repeating unit, a compound represented by the general formula: ##STR1## wherein, m and n, respectively, show the molar fraction of the quinonediimine structural unit and phenylenediamine structural unit in the repeating unit, and 0<m<1, 0<n<1, and m+n=1; and the organic polymer is soluble in an organic solvent in the undoped state, and has an intrinsic viscosity ?.eta.! of more than 0.4 dl/g measured in N-methyl-2-pyrrolidone at 30.degree. C. This invention also relates to a film formed of the conducting organic polymer and a conducting organic polymer composition.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: March 17, 1998
    Assignee: Nitto Denko Corporation
    Inventors: Masao Abe, Akira Ohtani, Hiroyuki Higuchi, Minoru Ezoe, Shinya Akizuki, Keiji Nakamoto, Keiko Mochizuki, Yasuhiro Umemoto, Michio Umeda
  • Patent number: 5720903
    Abstract: A dispersible, intrinsically conductive polymer having an electrical conductivity (measured in a 4-point measuring cell on a powder pellet) of 2.5.times.10.sup.1 to 2.5.times.10.sup.5 S/cm is obtained when a dispersible intrinsically conductive polymer in powder form having a starting conductivity of 1 to 5 S/cm is rubbed and/or dispersed in the presence of a non-polymeric polar substance applying sufficient shear forces until the desired increased electrical conductivity is reached.
    Type: Grant
    Filed: November 17, 1995
    Date of Patent: February 24, 1998
    Assignee: Zipperling Kessler & Co. (GmbH & Co)
    Inventors: Bernhard Wessling, Holger Merkle, Jr., Susanne Blattner
  • Patent number: 5700399
    Abstract: A soluble aniline conducting polymer characterized in that said conductive polymer comprises as a repeating unit an alkoxyl group-substituted aminobenzenesulfonic acid, its alkali metal salts, ammonium salts and/or substituted ammonium salts, and is a solid having a weight average molecular weight of about 1900 or more at room temperature, a conductive composition and electric conductor comprising the same, and a method for producing a soluble aniline conducting polymer having a weight average molecular weight of 10,000 t 3,240,000 characterized by polymerizing at least one compound (1) selected from the group consisting of an acidic group-substituted aniline, its alkali metal salts, ammonium salts and substituted ammonium salts in a solution containing a basic compound (2) using an oxidizing agent.
    Type: Grant
    Filed: August 21, 1996
    Date of Patent: December 23, 1997
    Assignee: Nitto Chemical Industry Co., Ltd.
    Inventors: Shigeru Shimizu, Takashi Saitoh, Masashi Uzawa, Yasuyuki Takayanagi
  • Patent number: 5696218
    Abstract: In a process for the preparation of poly-o-hydroxyamides and poly-o-mercaptoamides, a bis-o-hydroxyamide or a bis-o-mercaptoamide is reacted with a dihydroxy compound in the presence of a basic catalyst.
    Type: Grant
    Filed: August 29, 1996
    Date of Patent: December 9, 1997
    Assignee: Siemens Aktiengesellschaft
    Inventors: Recai Sezi, Hellmut Ahne, Roland Gestigkeit
  • Patent number: 5670603
    Abstract: This invention relates to polymers having non-linear optical properties which polymers include fluorene moieties having at least one electron accepting group and at least one electon donating group substituted to different phenyl rings of the fluorene moiety.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: September 23, 1997
    Assignee: AlliedSignal Inc.
    Inventors: Chengjiu Wu, Jianhui Shan, Ajay Nahata
  • Patent number: 5656862
    Abstract: Solder interconnection encapsulant, encapsulated structure and method for its fabrication and use, whereby the gap created by solder connections between a carrier substrate and a semiconductor device is filled with a composition obtained from curing a preparation containing a cycloaliphatic polyepoxide and/or curable cyanate ester or prepolymer thereof; filler, e.g., an aluminum nitride or aluminum oxide filler, having a maximum particle size of 31 microns.
    Type: Grant
    Filed: May 6, 1993
    Date of Patent: August 12, 1997
    Assignee: International Business Machines Corporation
    Inventors: Kostas I. Papathomas, David Wei Wang
  • Patent number: 5648448
    Abstract: New polyquinoline polymers are provided, as well as new methods for preparing the polyquinoline polymers using a novel combination of monomers. The polyquinoline polymers comprise repeat units comprising at least one quinoline nucleus and at least one ether linkage and having as end groups either fluoro groups or hydroxy groups or a combination of fluoro and hydroxy groups. The polymers are formed by providing a monomer comprising two fluoro groups, where each such fluoro group is activated by a quinoline nucleus, a diol monomer provided in the form of its bis-oxide salt, or in the presence of a base capable of deprotonating the diol and reacting the difluoro and diol monomers together in a dipolar solvent to form the polyquinoline polymer.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: July 15, 1997
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Matthew L. Marrocco, III, Ying Wang
  • Patent number: 5645764
    Abstract: An electrically conductive pressure sensitive adhesive containing electrically conductive polymers used as an alternative to metallic solder in interconnect electronic applications.
    Type: Grant
    Filed: January 19, 1995
    Date of Patent: July 8, 1997
    Assignee: International Business Machines Corporation
    Inventors: Marie Angelopoulos, Jeffrey Donald Gelorme, Joseph Paul Kuczynski
  • Patent number: 5646241
    Abstract: In accordance with the present invention, there are provided adhesive formulations containing small amounts of bleed control agent, which render the invention compositions extremely resistant to resin bleed. Several different types of bleed control agents are contemplated for use in the practice of the present invention, e.g., cationic surfactants, tertiary amines, tertiary phosphines, amphoteric surfactants, polyfunctional compounds, and the like, as well as mixtures of any two or more thereof.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 8, 1997
    Assignee: Quantum Materials, Inc.
    Inventors: Stephen M. Dershem, Deborah L. Derfelt
  • Patent number: 5637670
    Abstract: Novel molecular weight controlled and endcapped polybenzimidazoles (PBI) are prepared by the aromatic nucleophilic displacement reaction of di(hydroxyphenylbenzimidazole) monomers with activated aromatic dihalides or activated aromatic dinitro compounds. The PBI are endcapped with mono(hydroxyphenyl)benzimidazoles. 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. Mono(hydroxyphenyl)benzimidazoles are synthesized by reacting phenyl-4-hydroxybenzoate with aromatic (o-diamine)s in diphenylsulfone. Molecular weight controlled and endcapped PBI of new chemical structures are prepared that exhibit a favorable combination of physical and mechanical properties.
    Type: Grant
    Filed: January 20, 1995
    Date of Patent: June 10, 1997
    Assignee: The United States of America as represented by the Administrator, National Aeronautics and Space Administration
    Inventors: John W. Connell, Paul M. Hergenrother, Joseph G. Smith, Jr.
  • Patent number: 5626795
    Abstract: Optical quality transparent conductors such as bodies, films and coatings formed from substituted and unsubstituted polyanilines in nonconductive substrates such as polymers or polymer plus solvents with protonic acid are disclosed as are methods of forming such conductors from fluid forms of the polyaniline/substrate/acid mixtures.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: May 6, 1997
    Assignee: Uniax Corporation
    Inventors: Paul Smith, Alan J. Heeger, Yong Cao
  • Patent number: 5624605
    Abstract: Compositions of electrically conductive substituted and unsubstituted polyanilines in nonconductive substrates such as polymers or polymer plus solvents with protonic acids are disclosed as are methods of forming such compositions and use of same to form conductive articles.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: April 29, 1997
    Assignee: Uniax Corporation
    Inventors: Yong Cao, Paul Smith, Alan J. Heeger
  • Patent number: 5618469
    Abstract: The invention provides a solution comprising a proton-doped polyaniline in combination with a protonic acid which is a solvent thereof, and an article coated with an optically-transparent, electrically-conductive layer, formed from the solution, and comprising a proton-doped poiyaniline. The invention also provides a method for preparing a processable solution of a proton-doped polyaniline for use in the preparation of electrically-conductive and optically-transparent coatings, comprising oxidatively polymerizing aniline in the presence of a second protonic acid to yield a solid polyaniline; and dissolving the solid polyaniline in the first protonic acid.
    Type: Grant
    Filed: May 12, 1995
    Date of Patent: April 8, 1997
    Assignee: Al-Coat Ltd.
    Inventors: Eli Harlev, Tamilla Gulakhmedova, Ilya M. Rubinovich
  • Patent number: 5589565
    Abstract: A self-doped conducting polymer having along its backbone a .pi.-electron conjugated system which comprises a plurality of monomer units, between about 0.01 and 100 mole % of the units having covalently linked thereto at least one Bronsted acid group. The conductive zwitterionic polymer is also provided, as are monomers useful in the preparation of the polymer and electrodes comprising the polymer.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: December 31, 1996
    Assignee: The Regents of the University of California
    Inventors: Fred Wudl, Alan Heeger
  • Patent number: 5589108
    Abstract: A soluble aniline conducting polymer characterized in that said conductive polymer comprises as a repeating unit an alkoxyl group-substituted aminobenzenesulfonic acid, its alkali metal salts, ammonium salts and/or substituted ammonium salts, and is a solid having a weight average molecular weight of about 1900 or more at room temperature, a conductive composition and electric conductor comprising the same, and a method for producing a soluble aniline conducting polymer having a weight average molecular weight of 10,000 t 3,240,000 characterized by polymerizing at least one compound (1) selected from the group consisting of an acidic group-substituted aniline, its alkali metal salts, ammonium salts and substituted ammonium salts in a solution containing a basic compound (2) using an oxidizing agent.
    Type: Grant
    Filed: December 22, 1994
    Date of Patent: December 31, 1996
    Assignee: Nitto Chemical Industry Co., Ltd.
    Inventors: Shigeru Shimizu, Takashi Saitoh, Masashi Uzawa, Yasuyuki Takayanagi
  • Patent number: 5585040
    Abstract: The invention relates to a conductive polymer complex which contains a polyaniline or derivative thereof doped with a protonic acid. By the method according to the invention, a conductive polymer is obtained having substantially reduced acidity, sufficiently high conductivity level, and which is suitable, for example, for being melt processed in conventional plastics processing apparatus. The acidity of the conductive polymer can be reduced by having the conductive polymer contain both a metal compound and an additionally neutralizing compound. The obtained conductive polymer material, having a pH value of approximately 3-8, can be mixed with an insulating polymer to produce a conductive plastics mixture. The invention also relates to a method of preparing a conductive polymer that is more processable by incorporating therein a plasticizing agent selected from the group consisting of water, a C.sub.1 -C.sub.3 alcohol, and mixtures thereof.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: December 17, 1996
    Assignee: Neste Oy
    Inventors: Pauli Kirmanen, Esko Savolainen, Esa Virtanen, Toivo Karna, Jukka Laakso, Heikki Ruohonen, Kimmo Vakiparta, Olli Ikkala, Hannele Jarvinen
  • Patent number: 5583169
    Abstract: A stabilized non-conductive polyaniline solution comprising from about 1 to bout 10 percent by weight polyaniline or a polyaniline derivative, from about 90 to about 99 percent by weight N-methylpyrrolidone, and from about 0.5 percent by weight to about 15 percent by weight of a solution stabilizing additive selected from the group consisting of hindered amine light stabilizers, polymeric amines, and dialkylamines, percent by weight of additive based on the total weight of polyaniline or polyaniline derivative is provided together with a method for stabilizing a polyaniline solution.
    Type: Grant
    Filed: March 10, 1995
    Date of Patent: December 10, 1996
    Assignee: The Regents of the University of California Office of Technology Transfer
    Inventors: Debra A. Wrobleski, Brian C. Benicewicz
  • Patent number: 5567356
    Abstract: Electrically-conductive polyaniline salts that are soluble in xylene and an emulsion-polymerization process for producing the salts is disclosed. The process comprises the steps of combining water, a water soluble organic solvent, a hydrophobic organic acid, an aniline monomer, and a radical initiator and allowing the mixture to form the electrically-conductive polyaniline salt of the acid.
    Type: Grant
    Filed: November 7, 1994
    Date of Patent: October 22, 1996
    Assignee: Monsanto Company
    Inventor: Patrick J. Kinlen
  • Patent number: 5565544
    Abstract: A process for preparing a polyhydroxystyrene having a novolak type structure which comprises the step of polymerizing a mixture of carboxylic acid and at least one substituted phenyl carbinol whose formula is: ##STR1## wherein (a) R.sub.1 is selected from the group consisting of H, alkyl C.sub.1 -C.sub.20, substituted and unsubstituted phenyl, and C(O)R.sub.8 (where R.sub.8 is alkyl C.sub.1 -C.sub.20); (b) R.sub.2 is selected from the group consisting of H and alkyl C.sub.1 -C.sub.20 ; and (c) R.sub.3 -R.sub.7 are each independently selected from the group consisting of H, alkyl C.sub.1 -C.sub.20, OR.sub.9 (where R.sub.9 is H, alkyl C.sub.1 -C.sub.20, esters thereof, or substituted and unsubstituted phenyl), halogen, BZT, nitro, or amino, with the proviso that at least one of R.sub.3 -R.sub.7 is OR.sub.9, in the presence of a suitable catalyst for a sufficient period of time and under suitable conditions of temperature and pressure to form said novolak type polymer.
    Type: Grant
    Filed: June 16, 1995
    Date of Patent: October 15, 1996
    Assignee: Hoechst Celanese Corporation
    Inventor: James R. Sounik
  • Patent number: 5560870
    Abstract: A composition for forming an electrically conductive layer which is used in patterning of a resist with electric charge beam, which comprises:(a) 0.1 to 20 parts by weight of sulfonated polyanilines with a sulfonic group content ranging from 20 to 80% based on the aromatic ring, the sulfonated polyaniline having a weight average molecular weight of 500 to 100,000 and a molecular weight dispersion of not more than 5,(b) 100 parts by weight of a solvent, and(c) 0.01 to 30 parts by weight of amines and/or quaternary ammonium salts,and if desired, it further comprises 0 to 200 parts by weight of the following substance(s) (A) and/or (B) as component (d):(A) a high molecular weight compound soluble in the aforesaid solvent (b),(B) a surface active agent.
    Type: Grant
    Filed: May 22, 1995
    Date of Patent: October 1, 1996
    Assignees: Fujitsu Limited, Nitto Chemical Industry Co.
    Inventors: Keiji Watanabe, Yasuhiro Yoneda, Takashi Maruyama, Keiko Yano, Tomio Nakamura, Shigeru Shimizu, Takashi Saitoh
  • 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: 5540862
    Abstract: Colored, electrically conductive compositions comprising substituted and unsubstituted polyanilines and functionalized protonic acids and blends with insulating and semiconducting substrate polymers or polymers plus solvents are disclosed as are methods of forming colored electrically conductive articles of polyaniline/substrate/acid mixtures.
    Type: Grant
    Filed: March 18, 1994
    Date of Patent: July 30, 1996
    Assignee: Uniax Corporation
    Inventors: Yong Cao, Paul Smith
  • Patent number: 5541091
    Abstract: A process is described for the dimerization of a substituted aromatic compound of the formula (I): ##STR1## wherein X represents --OH, --SH or --NHR where R is H, an alkyl group or an aryl group; R.sup.1 and R.sup.2 represent an alkyl group, an aryl group, an alkenyl group, an alkynyl group, an alicyclic group, a halogen atom, an alkoxy group, an aryloxy group, a hydroxy group, or an amino group; and R.sup.3 and R.sup.4 can have the same definition as R.sup.1 and R.sup.2 and may additionally represent a hydrogen atom; which comprises reacting the substituted aromatic compound in the presence of a peroxidase enzyme, a peroxide and a radical transfer agent in an aqueous medium.
    Type: Grant
    Filed: April 5, 1995
    Date of Patent: July 30, 1996
    Assignee: Enzymol International, Inc.
    Inventors: Thurman M. Wheeler, Joseph Borovsky, Alexander Pokora
  • Patent number: 5534613
    Abstract: Polymers of the class rigid-rod aromatic heterocyclic polymers, having repeating units of the formula: ##STR1## wherein R is selected from the group consisting of --H, --CH.sub.3, --N(CH.sub.3).sub.2 and --OH, and Q is ##STR2## wherein X is --S-- or --O--, exhibit increased electrical conductivity, as compared to rigid-rod aromatic heterocyclic polymers polymers not containing the triarylamino moiety.
    Type: Grant
    Filed: January 26, 1995
    Date of Patent: July 9, 1996
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Loon-Seng Tan, Kasturi R. Srinivasan
  • Patent number: 5531932
    Abstract: Compositions and methods are described that relate to the use of reaction products of metal compounds and protonic acids for plasticizing and neutralizing acidic, protonated compositions comprising substituted and unsubstituted polyanilines and co-polymers and or mixtures thereof; and for reducing the percolation threshold for conductivity in blends with insulating bulk polymers.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: July 2, 1996
    Assignee: Neste Oy
    Inventors: Toivo Karna, Jukka Laakso, Timo Niemi, Heikki Ruohonen, Esko Savolainen, Helge Lindstrom, Esa Virtanen, Olli Ikkala
  • Patent number: 5521014
    Abstract: Crosslinkable, polyaromatic, polyether or polyester oligomers can have glass transition temperatures above 900.degree. F. while exhibiting desirable toughness for aerospace applications and ease of processing. A plurality (i.e. three or more) of generally linear aryl arms extend outwardly like spokes from a central aromatic hub through ether or ester linkages. Each spoke usually includes electronegative linkages, and is capped with one or two crosslinking functionalities (i.e. unsaturated hydrocarbon sites) which may be thermally or chemically activated to complete the advanced composite during curing. Among other methods, linear and multidimensional polyether oligomers are synthesized using nitrophthalic anhydride or halophthalic anhydride, dialcohols, or polyols, diamines, and suitable end caps.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: May 28, 1996
    Assignee: The Boeing Company
    Inventors: Hyman R. Lubowitz, Clyde H. Sheppard
  • Patent number: 5510535
    Abstract: Ether-linked amine-terminated polyethers are produced by reacting (1) a polyether polyol in which substantially all of the hydroxyl groups have been replaced with good leaving groups with (2) an aminoalcohol and/or aminothiol and (3) a deprotonating agent. The aminopolyethers obtained by this process are characterized by low viscosities and excellent reactivities over a wide range of molecular weights and functionalities.
    Type: Grant
    Filed: November 22, 1994
    Date of Patent: April 23, 1996
    Assignee: Bayer Corporation
    Inventors: Rick L. Adkins, William E. Slack
  • Patent number: 5498689
    Abstract: A modified polyphenylene ether comprising repeating units of the formula (1): ##STR1## wherein R.sub.1 and R.sub.2 are, independently from each other, a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms and having a number average polymerization degree of 20 to 12,000, in which 0.02/X to 1/X of methyl groups at the 2- and/or 6-positions of phenylene group are substituted by an aminomethyl group wherein X is a number average polymerization degree, a process for preparing the same, and a thermoplastic resin composition containing (A) 1 to 75% by weight of the above modified polyphenylene ether and (B) 99 to 25% by weight of a liquid crystalline polyester.Since this modified polyphenylene ether includes a highly reactive primary amine on the polymer side chain, it is preferably used in a wide range as a component of various compositions or polymer alloys. The thermoplastic resin composition is excellent in heat resistance, mechanical properties and appearance and gloss of a molded article.
    Type: Grant
    Filed: April 29, 1994
    Date of Patent: March 12, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Motonobu Furuta, Takanari Yamaguchi, Kazutoshi Ohashi
  • Patent number: 5498477
    Abstract: Electroactive polymers are provided which contain alternating phenyl rings and nitrogen atoms, and which contain both quinoid mer units and benzenoid mer units. The polymers are formed by poly(condensation) of N-phenylhydroxylamine or derivatives thereof under anhydrous conditions in the presence of a Lewis acid catalyst. Methods for producing films, fibers and shaped articles of the polymers are provided as well.
    Type: Grant
    Filed: January 31, 1994
    Date of Patent: March 12, 1996
    Assignee: Neste Oy
    Inventor: Floyd Klavetter