Halogen-containing Reactant Patents (Class 528/169)
  • Patent number: 10030101
    Abstract: Provided is a method of producing a branched polycarbonate, including: a step (a) of subjecting an alkali aqueous solution of a dihydric phenol, phosgene, and a branching agent to a phosgenation reaction in the presence of an organic solvent to provide a reaction liquid; a step (b) of adding the alkali aqueous solution of the dihydric phenol and a polymerization catalyst to the reaction liquid obtained from the step (a) to provide a reaction liquid containing a polycarbonate oligomer; a step (c) of separating the reaction liquid containing the polycarbonate oligomer obtained in the step (b) into an organic solvent phase containing the polycarbonate oligomer and an aqueous phase; and a step (d) of causing the organic solvent phase containing the polycarbonate oligomer separated in the step (c) and the alkali aqueous solution of the dihydric phenol to react with each other to provide a reaction liquid containing the branched polycarbonate, in which a ratio (x/y) of an addition amount of the polymerization catal
    Type: Grant
    Filed: November 6, 2015
    Date of Patent: July 24, 2018
    Assignee: IDEMITSU KOSAN CO., LTD.
    Inventors: Noriyuki Kunishi, Kazuhiro Sekiguchi, Yukiko Nagao, Masayuki Takahashi, Kenji Sasaki
  • Publication number: 20140221582
    Abstract: A hydroxyphenyl or alkoxyphenyl phosphine oxide composition comprising (i) a first mixture of mono-(hydroxyphenyl) or (alkoxyphenyl) phosphine oxide isomers, (ii) a second mixture of bis-(hydroxyaryl) or (alkoxyphenyl) phosphine oxide isomers, (iii) a third mixture of tris-(hydroxyaryl) or (alkoxyphenyl) phosphine oxide isomers, and optionally iv) a minority amount of non-hydroxy or non-alkoxy tris-phenyl phosphine oxides is provided. Also provided are epoxy resins compositions with excellent flame retardancy and physical properties, which resins comprise the phosphine oxide composition.
    Type: Application
    Filed: February 4, 2013
    Publication date: August 7, 2014
    Inventors: Larry D. Timberlake, Mark V. Hanson, James D. Sibecker
  • Publication number: 20140179858
    Abstract: A phosphorous copolymer, a method for preparing the same, and a flame retardant thermoplastic resin composition including the same is disclosed. The phosphorous copolymer includes a repeat unit represented by Formula 1: wherein each A is independently a single bond, C1 to C5 alkylene, C1 to C5 alkylidene, C5 to C6 cycloalkylidene, —S—, or —SO2—; R1 and R2 are each independently substituted or unsubstituted C1 to C6 alkyl or substituted or unsubstituted C6 to C20 aryl; R3 and R4 are each independently substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C3 to C6 cycloalkyl, substituted or unsubstituted C6 to C12 aryl, or halogen; a and b are each independently an integer from 0 to 4; and m and n are each independently an integer from 1 to 500.
    Type: Application
    Filed: July 23, 2013
    Publication date: June 26, 2014
    Applicant: Cheil Industries Inc.
    Inventors: Seung Woo JANG, Chang Hong KO
  • Publication number: 20140113093
    Abstract: A polymer which comprises recurring units derived from at least one monomer (M) having a general formula (I) Y1—Z1-Q-Z2—Y2 wherein Y1 and Y2, equal or different from each other, are independently selected from a group consisting of OH, SH, Cl, Br, NO2 or I; Z1 and Z2, equal or different from each other, independently comprises at least 1 aromatic ring and, Q comprises at least one hydrophilic moiety (H) selected from the group consisting of a sulfone (SO2), a ketone (CO), a phosphine oxide (PO), an ether, a thioether, an ester, an anhydride, a carbonate, an amide, an imide, an imine and an urethane group, and the interatomic distance between Y1 and Y2 is at least 10 ?, the monomer has an EC50 response value to the estrogen receptor a (ER?) equal to or at least 26000 nM.
    Type: Application
    Filed: May 24, 2012
    Publication date: April 24, 2014
    Applicant: SOLVAY SPECIALITY POLYMERS USA, LLC
    Inventors: George A. Corbin, Theodore Moore, Atul Bhatnagar
  • Publication number: 20130172471
    Abstract: Disclosed herein is a biphenyl polyphosphonate. The biphenyl polyphosphonate is represented by Formula 1: wherein R is hydrogen, substituted or unsubstituted C1-C5 alkyl, substituted or unsubstituted C2-C5 alkenyl, substituted or unsubstituted C5-C6 cycloalkyl, substituted or unsubstituted C5-C6 cycloalkenyl, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C6-C20 aryloxy, R1 and R2 are the same or different and are each independently substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C5-C6 cycloalkyl, substituted or unsubstituted C6-C12 aryl, or halogen, a and b are the same or different and are each independently an integer from about 0 to about 4, and n is an integer from about 4 to about 500.
    Type: Application
    Filed: October 16, 2012
    Publication date: July 4, 2013
    Applicant: CHEIL INDUSTRIES INC.
    Inventor: Cheil Industries Inc.
  • Publication number: 20120172506
    Abstract: A polyphosphonate having an acid value of about 5.5 mg KOH/g or less and represented by Formula 1: wherein: A is a single bond, C1 to C5 alkylene, C1 to C5 alkylidene, C5 to C6 cycloalkylidene, —S— or —SO2-, R is substituted or unsubstituted C6 to C20 aryl or substituted or unsubstituted C6 to C20 aryloxy, R1 and R2 are the same or different and are each independently substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C3 to C6 cycloalkyl, substituted or unsubstituted C6 to C 12 aryl or halogen, a and b are the same or different and are each independently an integer from about 0 to about 4, and n is an integer from about 1 to about 500.
    Type: Application
    Filed: December 20, 2011
    Publication date: July 5, 2012
    Applicant: CHEIL INDUSTRIES INC.
    Inventors: Min Soo LEE, Chang Hong KO, Seon Ae LEE, Sang Hyun HONG
  • Patent number: 8063111
    Abstract: Anion-conducing polymers and membranes with enhanced stability to aqueous alkali include a polymer backbone with attached sulfonium, phosphazenium, phosphazene, and guanidinium residues. Compositions also with enhanced stability to aqueous alkali include a support embedded with sulfonium, phosphazenium, and guanidinium salts.
    Type: Grant
    Filed: November 1, 2010
    Date of Patent: November 22, 2011
    Assignee: Los Alamos National Security, LLC
    Inventors: Bryan S. Pivovar, David L. Thorn
  • Patent number: 8022165
    Abstract: Process for preparing polymeric aromatic phosphonates and also polymeric aromatic phosphonates which can be prepared by the process of the invention and blends comprising these polymeric aromatic phosphonates and at least one further polymer and also films, composites and membranes comprising these polymers or blends, the use of the membranes of the invention in fuel cells or in separation technology and also fuel cells comprising the membranes of the invention.
    Type: Grant
    Filed: February 13, 2007
    Date of Patent: September 20, 2011
    Assignee: BASF SE
    Inventors: Helmut Moehwald, Thorsten Bock, Rolf Muelhaupt
  • Patent number: 8003749
    Abstract: Disclosed is a fluorine-containing dicarboxylic acid represented by formula (1), wherein n represents an integer of 1-4, and the two carboxylic groups are not adjacent to each other on the aromatic ring. It is possible to obtain a linear polymer compound by reacting the fluorine-containing dicarboxylic acid with a comonomer (e.g., diaminodiol). By thermal cyclization, this linear polymer compound can be converted into another polymer compound having superior characteristics.
    Type: Grant
    Filed: July 16, 2008
    Date of Patent: August 23, 2011
    Assignee: Central Glass Company, Limited
    Inventors: Satoru Narizuka, Yuji Hagiwara, Masashi Nagamori, Kazuhiro Yamanaka
  • Patent number: 7846980
    Abstract: Anion-conducing polymers and membranes with enhanced stability to aqueous alkali include a polymer backbone with attached sulfonium, phosphazenium, phosphazene, and guanidinium residues. Compositions also with enhanced stability to aqueous alkali include a support embedded with sulfonium, phosphazenium, and guanidinium salts.
    Type: Grant
    Filed: August 27, 2009
    Date of Patent: December 7, 2010
    Assignee: Los Alamos National Security, LLC
    Inventors: Bryan S. Pivovar, David L. Thorn
  • Publication number: 20090253840
    Abstract: Process for preparing polymeric aromatic phosphonates and also polymeric aromatic phosphonates which can be prepared by the process of the invention and blends comprising these polymeric aromatic phosphonates and at least one further polymer and also films, composites and membranes comprising these polymers or blends, the use of the membranes of the invention in fuel cells or in separation technology and also fuel cells comprising the membranes of the invention.
    Type: Application
    Filed: February 13, 2007
    Publication date: October 8, 2009
    Applicant: BASF SE
    Inventors: Helmut Möhwald, Thorsten Bock, Rolf Mülhaupt
  • Patent number: 7582683
    Abstract: Anion-conducing polymers and membranes with enhanced stability to aqueous alkali include a polymer backbone with attached sulfonium, phosphazenium, phosphazene, and guanidinium residues. Compositions also with enhanced stability to aqueous alkali include a support embedded with sulfonium, phosphazenium, and guanidinium salts.
    Type: Grant
    Filed: September 4, 2008
    Date of Patent: September 1, 2009
    Assignee: Los Alamos National Security, LLC
    Inventors: Bryan S. Pivovar, David L. Thorn
  • Patent number: 7511113
    Abstract: An aromatic ether oligomer or polyaromatic ether comprising the formula: O—Arn; wherein Ar is an independently selected divalent aromatic radical; formed by reacting a dihydroxyaromatic with a dihaloaromatic; and wherein the reaction is performed in the presence of a copper compound and cesium carbonate. The polyaromatic ether is formed when neither the dihydroxyaromatic nor the dihaloaromatic is present in an excess amount. The aromatic ether oligomer is formed by using an excess of either dihydroxyaromatic or dihaloaromatic. A phthalonitrile monomer comprising the formula: formed by reacting a 3- or 4-nitrophthalonitrile with a hydroxy-terminated aromatic ether oligomer. A thermoset formed by curing the phthalonitrile monomer. Processes for forming all the above.
    Type: Grant
    Filed: March 17, 2004
    Date of Patent: March 31, 2009
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Teddy M. Keller, Dawn D. Dominguez
  • Patent number: 7452959
    Abstract: An aromatic ether oligomer or polyaromatic ether comprising the formula: O—Arn; wherein Ar is an independently selected divalent aromatic radical; formed by reacting a dihydroxyaromatic with a dihaloaromatic; and wherein the reaction is performed in the presence of a copper compound and cesium carbonate. The polyaromatic ether is formed when neither the dihydroxyaromatic nor the dihaloaromatic is present in an excess amount. The aromatic ether oligomer is formed by using an excess of either dihydroxyaromatic or dihaloaromatic. A phthalonitrile monomer comprising the formula: formed by reacting a 3- or 4-nitrophthalonitrile with a hydroxy-terminated aromatic ether oligomer. A thermoset formed by curing the phthalonitrile monomer. Processes for forming all the above.
    Type: Grant
    Filed: March 17, 2004
    Date of Patent: November 18, 2008
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Teddy M. Keller, Dawn D. Dominguez
  • Patent number: 7442757
    Abstract: A thermoplastic resin contains a polymer, and the polymer includes a divalent phosphate residue having a spiro ring, represented by formula (1), in a molecule and has a number average molecular weight of at least 2,000: wherein R1 is independently selected from the group consisting of a hydrogen atom, a halogen atom, an aliphatic hydrocarbon group having the carbon number of 1 to 20, an aromatic hydrocarbon group having the carbon number of 1 to 20, and a nitro group; p and q are integers satisfying p+q=0 to 16; X independently represents oxygen, sulfur, selenium, or an unshared electron pair; Y is independently selected from oxygen, sulfur, and a methylene group; and n and m are integers satisfying n+m=0 to 4.
    Type: Grant
    Filed: May 13, 2003
    Date of Patent: October 28, 2008
    Assignee: Toray Industries, Inc.
    Inventors: Tatsuya Matsuno, Keijiro Takanishi
  • Patent number: 7439275
    Abstract: Anion-conducing polymers and membranes with enhanced stability to aqueous alkali include a polymer backbone with attached sulfonium, phosphazenium, phosphazene, and guanidinium residues. Compositions also with enhanced stability to aqueous alkali include a support embedded with sulfonium, phosphazenium, and guanidinium salts.
    Type: Grant
    Filed: March 22, 2006
    Date of Patent: October 21, 2008
    Assignee: Los Alamos National Security, LLC
    Inventors: Bryan S. Pivovar, David L. Thorn
  • Patent number: 7268193
    Abstract: Branched polyarylene polymers are provided comprising monovalent endcappers, divalent linear units, and polyvalent branching units. The composition of the polymers is controlled by adjusting the ratio of the three types of monomers.
    Type: Grant
    Filed: March 4, 2005
    Date of Patent: September 11, 2007
    Assignee: Mississippi Polymer Technologies, Inc.
    Inventors: Matthew L. Marrocco, III, Mark S. Trimmer, Ying Wang
  • Patent number: 7262265
    Abstract: A new family of high temperature thermoset resins having high glass transition temperatures and enhanced hygrothermal stability that are synthesized using inexpensive starting materials in essentially a single step process. A trifunctional aromatic, wherein at least one of the three functional groups comprises a halogen and the balance thereof comprises OH groups and wherein said aromatic has electron withdrawing properties, is polymerized using an excess of a diol.
    Type: Grant
    Filed: February 13, 2004
    Date of Patent: August 28, 2007
    Assignee: Solvay Advanced Polymers, L.L.C.
    Inventors: Farshad J. Motamedi, Matthew L. Marrocco, III
  • Patent number: 7144970
    Abstract: An insulating-film forming material comprising a resin (A) that has a structure represented by formula (I): wherein Y1, Y2, Ar1 and Ar2 are the same or different; each of Y1, Y2, Ar1 and Ar2represents an aromatic ring-containing divalent organic group; at least one of Y1 and Y2 is a divalent aromatic polycyclic group having a specific structure; m and n each indicates a molar percentage of the repeating units; and m falls between 0 and 100 with (m+n)=100.
    Type: Grant
    Filed: March 22, 2004
    Date of Patent: December 5, 2006
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Yutaka Adegawa
  • Patent number: 6989420
    Abstract: Coating liquid for producing insulating film having low dielectric constant is provided. It was achieved by coating liquid for producing insulating film having low dielectric constant comprising a thermosetting resin having carbon-carbon unsaturated bond, an organic solvent, and less than two molecular equivalents of water to the carbon-carbon unsaturated bond.
    Type: Grant
    Filed: November 25, 2002
    Date of Patent: January 24, 2006
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yuji Yoshida, Naoya Satoh
  • Patent number: 6878796
    Abstract: Aromatic aliphatic ether solvents, such as anisole, methylanisole, and phenetole, have been found useful in formulating coating solutions of polymeric dielectric materials and as a clean up solvent in the coating process. A process for forming a dielectric film on a substrate includes depositing a coating solution of a dielectric material in a formulation solvent onto a surface of the substrate and depositing an aromatic aliphatic ether solvent onto an edge portion of the surface of the substrate. The process is used to form films of dielectric materials including arylene ether dielectric polymers, hydridosiloxane resins, organohydridosiloxane resins, spin-on-glass materials, partially hydrolyzed and partially condensed alkoxysilane compositions which are cured to form a nanoporous dielectric silica material, and poly(perhydrido)silazanes.
    Type: Grant
    Filed: November 18, 2002
    Date of Patent: April 12, 2005
    Assignee: Honeywell International Inc.
    Inventors: Oana Leonte, Tadashi Nakano, Kelly Beres, Kreisler Lau
  • Patent number: 6756470
    Abstract: An aromatic ether oligomer or polyaromatic ether comprising the formula: wherein Ar is an independently selected divalent aromatic radical; formed by reacting a dihydroxyaromatic with a dihaloaromatic; and wherein the reaction is performed in the presence of a copper compound and cesium carbonate. The polyaromatic ether is formed when neither the dihydroxyaromatic nor the dihaloaromatic is present in an excess amount. The aromatic ether oligomer is formed by using an excess of either dihydroxyaromatic or dihaloaromatic. A phthalonitrile monomer comprising the formula: formed by reacting a 3- or 4-nitrophthalonitrile with a hydroxy-terminated aromatic ether oligomer. A thermoset formed by curing the phthalonitrile monomer. Processes for forming all the above.
    Type: Grant
    Filed: April 26, 2002
    Date of Patent: June 29, 2004
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Teddy M. Keller, Dawn D. Dominguez
  • Publication number: 20030191275
    Abstract: Aromatic aliphatic ether solvents, such as anisole, methylanisole, and phenetole, have been found useful in formulating coating solutions of polymeric dielectric materials and as a clean up solvent in the coating process. A process for forming a dielectric film on a substrate includes depositing a coating solution of a dielectric material in a formulation solvent onto a surface of the substrate and depositing an aromatic aliphatic ether solvent onto an edge portion of the surface of the substrate. The process is used to form films of dielectric materials including arylene ether dielectric polymers, hydridosiloxane resins, organohydridosiloxane resins, spin-on-glass materials, partially hydrolyzed and partially condensed alkoxysilane compositions which are cured to form a nanoporous dielectric silica material, and poly(perhydrido)silazanes.
    Type: Application
    Filed: November 18, 2002
    Publication date: October 9, 2003
    Inventors: Oana Leonte, Tadashi Nakano, Kelly Beres, Kreisler Lau
  • Patent number: 6566483
    Abstract: This invention discloses a photosensitive phosphorylated phenol-formaldehyde resin, characterized by containing in its molecule at least two phosphate groups, each phosphate group coupled with at least one photo-sensitive group. The photosensitive resin of the present invention is prepared by reacting a phenol-formaldehyde resin with phosphorus oxychloride to form a phosphorylated phenol-formaldehyde resin; then reacting the resin with a compound having one hydroxyl group and at least one ethylenically unsaturated bond, thereby esterifying some of the phosphorochloridate groups to produce a resin having ethylenically unsaturated bonds and unreacted phosphorochloridate groups; and hydrolyzing the unreacted phosphorochloridate groups into phosphoric groups. The photosensitive resin according to the invention is UV-curable and alkaline-soluble as traditional photosensitive resins are; moreover, it exhibits good flame retardant and adhesive properties.
    Type: Grant
    Filed: September 27, 2001
    Date of Patent: May 20, 2003
    Assignee: Industrial Technology Research Institute
    Inventors: Ching-Sheng Cho, Shinn-Jen Chang, Wan-Jung Teng, Jiun-Ji Chen
  • Patent number: 6524657
    Abstract: Aromatic aliphatic ether solvents, such as anisole, methylanisole, and phenetole, have been found useful in formulating coating solutions of polymeric dielectric materials and as a clean up solvent in the coating process. A process for forming a dielectric film on a substrate includes depositing a coating solution of a dielectric material in a formulation solvent onto a surface of the substrate and depositing an aromatic aliphatic ether solvent onto an edge portion of the surface of the substrate. The process is used to form films of dielectric materials including arylene ether dielectric polymers, hydridosiloxane resins, organohydridosiloxane resins, spin-on-glass materials, partially hydrolyzed and partially condensed alkoxysilane compositions which are cured to form a nanoporous dielectric silica material, and poly(perhydrido)silazanes.
    Type: Grant
    Filed: May 7, 2002
    Date of Patent: February 25, 2003
    Assignee: Honeywell International Inc.
    Inventors: Oana M. Leonte, Tadashi Nakano, Kelly M. Beres, Kreisler Lau
  • Publication number: 20020183476
    Abstract: Aromatic aliphatic ether solvents, such as anisole, methylanisole, and phenetole, have been found useful in formulating coating solutions of polymeric dielectric materials and as a clean up solvent in the coating process. A process for forming a dielectric film on a substrate includes depositing a coating solution of a dielectric material in a formulation solvent onto a surface of the substrate and depositing an aromatic aliphatic ether solvent onto an edge portion of the surface of the substrate. The process is used to form films of dielectric materials including arylene ether dielectric polymers, hydridosiloxane resins, organohydridosiloxane resins, spin-on-glass materials, partially hydrolyzed and partially condensed alkoxysilane compositions which are cured to form a nanoporous dielectric silica material, and poly(perhydrido)silazanes.
    Type: Application
    Filed: May 7, 2002
    Publication date: December 5, 2002
    Applicant: Honeywell International Inc.
    Inventors: Oana M. Leonte, Tadashi Nakano, Kelly M. Beres, Kreisler Lau
  • Patent number: 6303733
    Abstract: Dielectric compositions encompassing one or more poly(arylene ether) polymers are provided. The dielectric compositions have the repetitive structural unit: where n=1 to 200, Y and Ar are each a divalent arylene radical, Y derived from bisphenol compounds of general formula HO—Y—OH, Ar derived from difluoro diarylacetylenes and/or ethynylated benzophenones of general formula F—Ar—F and Z is optionally hydrogen, a methyl group or derived from a monofluoro-benzophenone derivative of general formula Z—F. Such poly(arylene ether) polymers are employed with a variety of microelectronic devices, for example, integrated circuits and multichip modules.
    Type: Grant
    Filed: November 20, 1998
    Date of Patent: October 16, 2001
    Assignee: AlliedSignal Inc.
    Inventors: Kreisler S. Y. Lau, Tian-An Chen, Boris A. Korolev, Emma Brouk
  • Patent number: 6291628
    Abstract: A polymeric low dielectric constant solution includes a low dielectric constant polymer dissolved in an aromatic aliphatic ether solvent. The polymer preferably is a poly(arylene ether) and the solvent preferably is anisole, methylanisole, phenetole or mixtures thereof. A process for forming a dielectric film on a substrate by spin-coating the polymeric solution is also provided.
    Type: Grant
    Filed: January 21, 1999
    Date of Patent: September 18, 2001
    Assignee: Allied Signal Inc.
    Inventors: Tian-An Chen, Kreisler S. Y. Lau, Qiang Zhao
  • Patent number: 6124421
    Abstract: Dielectric compositions encompassing one or more poly(arylene ether) polymers are provided. The dielectric compositions have the repetitive structural unit: ##STR1## where n=0 to 1; m=0 to 1-n; and Y.sub.1, Y.sub.2, Ar.sub.1 and Ar.sub.2 are each a divalent arylene radical, Y.sub.1 and Y.sub.2 derived from biphenol compounds, Ar.sub.1 derived from difluoroarylethynes and Ar.sub.2 derived from difluoroaryl compounds. Where both Y.sub.1 and Y.sub.2 are derived from fluorene bisphenol, n=0.1 to 1. Such poly(arylene ether) polymers are employed with a variety of microelectronic devices, for example, integrated circuits and multichip modules.
    Type: Grant
    Filed: December 12, 1997
    Date of Patent: September 26, 2000
    Assignee: AlliedSignal Inc.
    Inventors: Kreisler S. Y. Lau, Tian-An Chen, Boris A. Korolev, Emma Brouk, Paul E. Schilling, Heike W. Thompson
  • Patent number: 6040416
    Abstract: A melt polymerization method for producing poly(arylene ethers phosphine oxide)s suited to optical applications comprising reacting a trimethyl silyl derivative of bisphenol and an activated aromatic dihalide, wherein either reactant is a phosphine oxide, is provided.
    Type: Grant
    Filed: February 18, 1999
    Date of Patent: March 21, 2000
    Assignees: Johnson & Johnson Vision Products, Inc., Virginia Tech Intellectual Properties, Inc.
    Inventors: Venkateshwaran N. Sekharipuram, Beverly Sue Mecham, Atul Bhatnagar, James E. McGrath
  • Patent number: 5914388
    Abstract: A process for the preparation of polyphosphazenes is provided that includes the cationic solution polymerization reaction of a phosphoranimine, using a main group or transition metal halide, or other appropriate halide salt, including a linear phosphazene salt of any chain length, or a preformed non-phosphazene polymer containing a main or transition metal chloride, as an initiator. In a preferred embodiment, triarmed-star polyphosphazenes having the formula N{RN(H)R'.sub.2 P--(N.dbd.PR'.sub.2).sub.n }.sub.3 are prepared via this method. Also, a methods for synthesis of the monomer Cl.sub.3 P.dbd.NSiMe.sub.3 and cyclic trimer N.sub.3 P.sub.3 X.sub.6 from the reactants N(SiR.sub.3).sub.3 and PX.sub.5 are also described.
    Type: Grant
    Filed: August 22, 1997
    Date of Patent: June 22, 1999
    Assignee: The Penn State Research Foundation
    Inventors: Harry R. Allcock, Christopher T. Morrissey, Ian Manners, Charles H. Honeyman, James M. Nelson, Chester A. Crane, Scott D. Reeves, A. Paul Primrose, Thomas J. Hartle, R. Prange
  • Patent number: 5898062
    Abstract: Poly (organophosphazene) polymers bearing various ratios of a carboxylic acid containing sidegroup and an alkylamino, alkoxy, or alkoxy ether sidegroup are disclosed. These water-soluble macromolecules are cross-linked and allowed to absorb water to form hydrogels. Because of their anionic character and high water content, the polymeric hydrogels are useful for a wide variety of biomedical applications including controlled drug delivery (e.g. pH sensitive drug delivery), biocompatible coatings, and pH sensitive membranes.
    Type: Grant
    Filed: April 10, 1997
    Date of Patent: April 27, 1999
    Assignee: The Penn State Research Foundation
    Inventors: Harry R. Allcock, Archel M. A. Ambrosio
  • Patent number: 5698664
    Abstract: A process for the preparation of polyphosphazenes is provided that includes the cationic solution polymerization reaction of a phosphoranimine, using a main group or transition metal halide, or other appropriate halide salt, including a linear phosphazene salt of any chain length, or a preformed nonphosphazene polymer containing a main or transition metal chloride, as an initiator.
    Type: Grant
    Filed: April 26, 1995
    Date of Patent: December 16, 1997
    Assignees: The Penn State Research Foundation, University of Toronto
    Inventors: Harry R. Allcock, Christopher T. Morrissey, Ian Manners, Charles H. Honeyman
  • Patent number: 5548060
    Abstract: A method for the alkylsulfonation of polymeric and cyclic trimer phosphazenes that includes reacting the phosphazene with a sultone. This method can be used to prepare sulfonated phosphazenes that are useful as biomedical materials, membranes, reversibly cross-linkable polymers, surfactants, and polyelectrolytes.
    Type: Grant
    Filed: August 8, 1994
    Date of Patent: August 20, 1996
    Assignee: Penn State Research Foundation, Inc.
    Inventors: Harry R. Allcock, Eric H. Klingenberg, Mark P. Weller
  • Patent number: 5464932
    Abstract: Chalcone and cinnamate bearing polyphosphazenes are disclosed. The polyphusphazenes contain a sufficient number of chalcone or cinnamate groups, or a combination thereof, to achieve a photocrosslinkable material. The phosphazene backbone is transparent from the near and mid-UV to the near infrared region, minimizing degradation of the skeleton both under the high intensity UV irradiation required for the photo-crosslinking reaction and during subsequent exposure to light disclosed. These photosensitive polyphosphazenes are useful for a variety of purposes, including in photolithography, photocurable coatings, for the stabilization of certain non-linear optical properties, and for use in the construction of biocompatible semi-permeable membranes which can be used to encapsulate living cells or other substances of implantation.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: November 7, 1995
    Assignee: The Penn State Research Foundation
    Inventors: Harry R. Allcock, Charles G. Cameron, Dawn E. Smith
  • Patent number: 5399654
    Abstract: A phosphorus-containing wholly aromatic polyester is produced by an interfacial polymerization method which includes the step of reacting a phosphorus-containing bisphenol compound and a bisphenol compound with dicarboxylic acid chlorides. An organic layer containing the dicarboxylic acid chlorides and phase transfer catalyst is added into an alkaline aqueous layer which contains a bisphenol compound.
    Type: Grant
    Filed: October 21, 1993
    Date of Patent: March 21, 1995
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Young H. Ko, Seung D. Cho, Byung C. Jeon
  • Patent number: 5384337
    Abstract: A poromeric material for maintaining an electrostatic charge is provided, the material including a matrix of fibers, a polymeric binder for binding the matrix, and electrets present substantially uniformly throughout the poromeric material. Also provided are methods for making the poromeric material. In one embodiment, a polymeric binder mixture having electrets substantially uniformly contained therein is formed. The matrix of fibers is impregnated with the mixture and cured, whereby the electrets are substantially uniformly distributed throughout the matrix to produce the electrostatic poromeric material. In an alternative embodiment, the electrets are contained in the fibers of the matrix. The poromeric material may be used to encase a core to form a roller, for example, a hickey-removing roller.
    Type: Grant
    Filed: February 5, 1993
    Date of Patent: January 24, 1995
    Inventor: William D. Budinger
  • Patent number: 5312890
    Abstract: Bisphosphine oxide monomers and homologs thereof may be incorporated into polycarbonates in order to obtain a flame retardant polymer. More particularly, bis[2,5-(diphenylphosphine oxide)]-1,4-hydroquinone and homologs thereof may be used to prepare flame retardant polycarbonates that retain high glass transition temperature and high impact resistances.
    Type: Grant
    Filed: April 22, 1993
    Date of Patent: May 17, 1994
    Assignee: General Electric Company
    Inventor: Gary C. Davis
  • Patent number: 5310855
    Abstract: The aromatic formaldehyde condensation products, which are substantially colorless and water-soluble and contain sulphonate and/or carboxylate groups, are obtainable by adding agents which have a reducing action during and/or after the condensation reaction, and are suitable for the treatment of textiles and leather.
    Type: Grant
    Filed: November 13, 1992
    Date of Patent: May 10, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Walz, Udo Hendricks, Hans-Albert Ehlert, Fritz Lesszinsky
  • Patent number: 5304625
    Abstract: Phosphazene-containing amines having at least one amine or substituted amine moiety reactive with nitrile groups of the phthalonitrile monomers or oligomeric resins are useful curing agents for phthalonitriles. Typically, the phosphazene-containing amines useful as curing agents in the present invention have the formula: ##STR1## wherein each of X.sub.1-6 is a hydrogen, an unsubstituted amine group, or an amine group substituted with C.sub.1 -C.sub.12 alkyl groups or aromatic groups, at least one of X.sub.1-6 includes an amine group, and each of R'.sub.1-6 is an alkyl, aromatic, or alkyl-substituted aromatic moiety, or a linear polymer of the phosphazene-based amine monomer. The curing agents enhance the speed of cure and also add flame retardancy to the cured polymers.
    Type: Grant
    Filed: February 19, 1993
    Date of Patent: April 19, 1994
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Teddy M. Keller
  • Patent number: 5208318
    Abstract: Phosphazene-containing amines having at least one amine or substituted amine moiety reactive with nitrile groups of the phthalonitrile monomers or oligomeric resins are useful curing agents for phthalonitriles. Typically, the phosphazene-containing amines useful as curing agents in the present invention have the formula: ##STR1## wherein each of X.sub.1-6 is a hydrogen, an unsubstituted amine group, or an amine group substituted with C.sub.1 -C.sub.12 alkyl groups or aromatic groups, at least one of X.sub.1-6 includes an amine group, and each of R'.sub.1-6 is an alkyl, aromatic, or alkyl-substituted aromatic moiety, or a linear polymer of the phosphazene-based amine monomer. The curing agents enhance the speed of cure and also add flame retardancy to the cured polymers.
    Type: Grant
    Filed: March 15, 1991
    Date of Patent: May 4, 1993
    Inventor: Teddy M. Keller
  • Patent number: 5194564
    Abstract: Novel flame retardant polycarbonates are prepared that maintain a T.sub.g and an impact strength similar to that of non-modified polycarbonates. More particular, phosphine oxide containing polycarbonates are prepared that demonstrate improved flame retardancy and the retention of impact strength and glass transition temperature.
    Type: Grant
    Filed: June 18, 1992
    Date of Patent: March 16, 1993
    Assignee: General Electric Company
    Inventors: Gary C. Davis, Christianus A. A. Claesen, Erwin M. A. Gijzen
  • Patent number: 5182356
    Abstract: Poly(1,2,4-triazoles)(PT) have been prepared by involving the aromatic nucleophilic displacement reaction of di(hydroxyphenyl)-1,2,4-triazole monomers with activated aromatic dihalides or activated aromatic dinitro compounds. The reactions are carried out in polar aprotic solvents such as sulfolane or diphenylsulfone using alkali metal bases such as potassium carbonate at elevated temperatures under nitrogen. The di(hydroxyphenyl)-1,2,4-triazole monomers are first synthesized by reacting bis(4-hydroxyphenyl) hydrazide with aniline hydrochloride at 250.degree. C. in the melt and also by reacting 1,3 or 1,4-bis-(4-hydroxyphenyl)phenylenedihydrazide with 2 moles of aniline hydrochloride in the melt. Purification of the di(hydroxyphenyl)-1,2,4-triazole monomers is accomplished by recrystallization.
    Type: Grant
    Filed: January 24, 1991
    Date of Patent: January 26, 1993
    Assignee: The United States of America as represented by the United States National Aeronautics and Space Administration
    Inventors: John W. Connell, Paul M. Hergenrother, Peter Wolf
  • Patent number: 5145936
    Abstract: A fluorinated poly(naphthyl ether) having a repeat unit of the formula ##STR1## wherein Y is (CF.sub.2).sub.m, ##STR2## m is an integer from 1 to 4, inclusive, and X is S, CO, SO.sub.2, O, P(C.sub.6 H.sub.5), or C(OH)H. Such polymers are useful as low dielectric constant, low moisture absorption insulators for multilayered integrated circuit articles, especially in their crosslinked form.
    Type: Grant
    Filed: September 6, 1991
    Date of Patent: September 8, 1992
    Assignee: Raychem Corporation
    Inventor: Frank Mercer
  • Patent number: 5101002
    Abstract: Phosphazene polymers having the units ##STR1## wherein the total number of units ranges from about 3 to about 50,000, R.sub.1 and R.sub.2 are different and are C.sub.1 to C.sub.12 linear or branched alkyl, C.sub.2 to C.sub.15 linear or branched fluoroalkyl or mixtures thereof, and R.sub.3 is phenyl substituted with C.sub.1 to C.sub.12 linear or branched alkyl. The polymers can be cured with peroxides to yield cross-linked materials having enhanced elongation.
    Type: Grant
    Filed: September 24, 1990
    Date of Patent: March 31, 1992
    Assignee: Ethyl Corporation
    Inventors: W. Dirk Klobucar, David M. Indyke
  • Patent number: 5089534
    Abstract: This invention relates to the use of phosphorus-containing compounds, specifically cyclic organophosphorus compounds, as carbodiimidization catalysts in the preparation of open-celled flexible polyurethane foam for the purpose of controlling foam density and providing softer foams. foams that are softer and of lower density can be prepared with significantly reduced quantities of blowing agents in comparison to foams prepared in the absence of such phosphorus-containing compounds. Additionally, use of such catalysts provides for a reduced reaction exotherm during the preparation of the foam thereby minimizing foam discoloration or scorching. Preferred phosphorus-containing compounds are the 1-alkyl-1-oxophospholenes, especially 1-methyl-1-oxophospholene.
    Type: Grant
    Filed: March 23, 1990
    Date of Patent: February 18, 1992
    Assignee: The Dow Chemical Company
    Inventors: Johan A. Thoen, Robert A. Sewell, Ulrich Muller
  • Patent number: 5079333
    Abstract: Amine-terminated poly(arylene ether phosphine oxide) oligomers of the general formula ##STR1## where Ar' is phenyl, biphenyl, bisphenol-A, etc., can be formed by reaction of a bisphenol monomer, a dihalo triphenyl phosphine oxide monomer, and an aminophenol.
    Type: Grant
    Filed: July 13, 1990
    Date of Patent: January 7, 1992
    Assignee: Virginia Tech Intellectual Properties, Inc.
    Inventors: James E. McGrath, Carrington D. Smith
  • Patent number: 5053451
    Abstract: Hexachlorocyclotriphosphazene and poly(dichlorophosphazene) react with the sodium salt of ethyl p-hydroxybenzoate to give small molecule cyclic and high polymeric phosphazenes with aryloxy ester side groups; reaction of these compounds with potassium tert-butoxide brings about complete hydrolysis of the ester groups to yielding aqueous media-soluble, carboxylic acid bearing cyclic and high polymeric phosphazenes; the carboxylic acid bearing high polymer formed ionic cross-links when treated in aqueous media with salts of di- or trivalent cations yield hydrogels and membranes. The cross-linked gels were stable in neutral or strongly acidic aqueous media, but the cross-linking process was reversed in basic aqueous solutions of excess monovalent cations.
    Type: Grant
    Filed: January 19, 1990
    Date of Patent: October 1, 1991
    Assignee: The Pennsylvania Research Corporation
    Inventors: Harry R. Allcock, Sukky Kwon
  • Patent number: 5041524
    Abstract: Polyphosphazene derivatives containing carbonyl groups which are apt to undergo rapid photoreticulation processes having the general formula ##STR1## in which: X represents substituents bound to the polyphosphazene chains by means of hydroxy or amino functions, and containing carbonyl groups;X' represents additional substituents bound to the polyphosphazene chain through hydroxy or amino functions and containing one or more easily extractable hydrogen atoms;(w+y+z) is an integer between 20 and 15,000;w and z are integers greater than or equal to 0 and always lower than 15.000;y is an integer between 20 and 15,000.
    Type: Grant
    Filed: November 16, 1989
    Date of Patent: August 20, 1991
    Assignee: Consiglio Nazionale Delle Ricerche
    Inventors: Mario Gleria, Francesco Minto, Lucia Flamigni
  • Patent number: 4990588
    Abstract: What are disclosed are aromatic polyethers which are resistant to high temperature, having a reduced viscosity greater than 0.25 dl/g and a repeating structural unit[(A-O).sub.a (B-O).sub.b (C-O).sub.c ],wherein A is 5a,10b-diphenyl-coumarano[2',3',2,3]coumaran of the formula ##STR1## B has the formula ##STR2## wherein n is 0 or 1, and X is ##STR3## and/or ##STR4## and C is at least one further aromatic unit.
    Type: Grant
    Filed: February 8, 1989
    Date of Patent: February 5, 1991
    Assignee: Rohm GmbH
    Inventors: Joachim Knebel, Werner Ude, Joachim Vetter