Halogen-containing Reactant Patents (Class 528/169)
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Patent number: 12122921Abstract: The invention provides chemical conjugates comprising a plurality of fluorescence quenching moieties conjugated to polymer and the use of such conjugates to quench the emission of fluorescence from emitters including macromolecular fluorescent emitters such as phycoerythrin.Type: GrantFiled: June 30, 2021Date of Patent: October 22, 2024Assignee: ENZO BIOCHEM, INC.Inventors: Elazar Rabbani, Jack Coleman
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Patent number: 12071559Abstract: A coating composition includes: (a) an acid functional polyol polymer having an acid value of greater than 9 mg KOH/g and less than 60 mg KOH/g, and a hydroxyl value of from 100 to 300 mg KOH/g; (b) a non-aminoplast derived crosslinker reactive with the acid functional polyol polymer; and (c) a non-aqueous liquid medium. Further, an equivalent ratio of functional groups on the crosslinker reactive with hydroxyl functional groups to hydroxyl functional groups on the acid functional polyol polymer is within a range of from 0.5 to 1.5. The coating composition is substantially free of an external catalyst. The coating composition cures at a temperature of less than 80° C.Type: GrantFiled: November 1, 2019Date of Patent: August 27, 2024Assignee: PPG Industries Ohio, Inc.Inventors: Ian Michael Jones, Egle Puodziukynaite, Shanti Swarup, James C. Serene, Paul H. Lamers, Steven V. Barancyk, Craig A. Wilson
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Patent number: 10030101Abstract: 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 catalType: GrantFiled: November 6, 2015Date of Patent: July 24, 2018Assignee: IDEMITSU KOSAN CO., LTD.Inventors: Noriyuki Kunishi, Kazuhiro Sekiguchi, Yukiko Nagao, Masayuki Takahashi, Kenji Sasaki
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Publication number: 20140221582Abstract: 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: ApplicationFiled: February 4, 2013Publication date: August 7, 2014Inventors: Larry D. Timberlake, Mark V. Hanson, James D. Sibecker
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Publication number: 20140179858Abstract: 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: ApplicationFiled: July 23, 2013Publication date: June 26, 2014Applicant: Cheil Industries Inc.Inventors: Seung Woo JANG, Chang Hong KO
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Publication number: 20140113093Abstract: 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: ApplicationFiled: May 24, 2012Publication date: April 24, 2014Applicant: SOLVAY SPECIALITY POLYMERS USA, LLCInventors: George A. Corbin, Theodore Moore, Atul Bhatnagar
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Publication number: 20130172471Abstract: 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: ApplicationFiled: October 16, 2012Publication date: July 4, 2013Applicant: CHEIL INDUSTRIES INC.Inventor: Cheil Industries Inc.
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Publication number: 20120172506Abstract: 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: ApplicationFiled: December 20, 2011Publication date: July 5, 2012Applicant: CHEIL INDUSTRIES INC.Inventors: Min Soo LEE, Chang Hong KO, Seon Ae LEE, Sang Hyun HONG
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Patent number: 8063111Abstract: 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: GrantFiled: November 1, 2010Date of Patent: November 22, 2011Assignee: Los Alamos National Security, LLCInventors: Bryan S. Pivovar, David L. Thorn
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Patent number: 8022165Abstract: 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: GrantFiled: February 13, 2007Date of Patent: September 20, 2011Assignee: BASF SEInventors: Helmut Moehwald, Thorsten Bock, Rolf Muelhaupt
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Patent number: 8003749Abstract: 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: GrantFiled: July 16, 2008Date of Patent: August 23, 2011Assignee: Central Glass Company, LimitedInventors: Satoru Narizuka, Yuji Hagiwara, Masashi Nagamori, Kazuhiro Yamanaka
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Patent number: 7846980Abstract: 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: GrantFiled: August 27, 2009Date of Patent: December 7, 2010Assignee: Los Alamos National Security, LLCInventors: Bryan S. Pivovar, David L. Thorn
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Publication number: 20090253840Abstract: 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: ApplicationFiled: February 13, 2007Publication date: October 8, 2009Applicant: BASF SEInventors: Helmut Möhwald, Thorsten Bock, Rolf Mülhaupt
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Patent number: 7582683Abstract: 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: GrantFiled: September 4, 2008Date of Patent: September 1, 2009Assignee: Los Alamos National Security, LLCInventors: Bryan S. Pivovar, David L. Thorn
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Patent number: 7511113Abstract: 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: GrantFiled: March 17, 2004Date of Patent: March 31, 2009Assignee: The United States of America as represented by the Secretary of the NavyInventors: Teddy M. Keller, Dawn D. Dominguez
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Patent number: 7452959Abstract: 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: GrantFiled: March 17, 2004Date of Patent: November 18, 2008Assignee: The United States of America as represented by the Secretary of the NavyInventors: Teddy M. Keller, Dawn D. Dominguez
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Patent number: 7442757Abstract: 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: GrantFiled: May 13, 2003Date of Patent: October 28, 2008Assignee: Toray Industries, Inc.Inventors: Tatsuya Matsuno, Keijiro Takanishi
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Patent number: 7439275Abstract: 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: GrantFiled: March 22, 2006Date of Patent: October 21, 2008Assignee: Los Alamos National Security, LLCInventors: Bryan S. Pivovar, David L. Thorn
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Patent number: 7268193Abstract: 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: GrantFiled: March 4, 2005Date of Patent: September 11, 2007Assignee: Mississippi Polymer Technologies, Inc.Inventors: Matthew L. Marrocco, III, Mark S. Trimmer, Ying Wang
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Patent number: 7262265Abstract: 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: GrantFiled: February 13, 2004Date of Patent: August 28, 2007Assignee: Solvay Advanced Polymers, L.L.C.Inventors: Farshad J. Motamedi, Matthew L. Marrocco, III
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Patent number: 7144970Abstract: 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: GrantFiled: March 22, 2004Date of Patent: December 5, 2006Assignee: Fuji Photo Film Co., Ltd.Inventor: Yutaka Adegawa
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Patent number: 6989420Abstract: 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: GrantFiled: November 25, 2002Date of Patent: January 24, 2006Assignee: Sumitomo Chemical Company, LimitedInventors: Yuji Yoshida, Naoya Satoh
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Patent number: 6878796Abstract: 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: GrantFiled: November 18, 2002Date of Patent: April 12, 2005Assignee: Honeywell International Inc.Inventors: Oana Leonte, Tadashi Nakano, Kelly Beres, Kreisler Lau
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Patent number: 6756470Abstract: 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: GrantFiled: April 26, 2002Date of Patent: June 29, 2004Assignee: The United States of America as represented by the Secretary of the NavyInventors: Teddy M. Keller, Dawn D. Dominguez
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Publication number: 20030191275Abstract: 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: ApplicationFiled: November 18, 2002Publication date: October 9, 2003Inventors: Oana Leonte, Tadashi Nakano, Kelly Beres, Kreisler Lau
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Patent number: 6566483Abstract: 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: GrantFiled: September 27, 2001Date of Patent: May 20, 2003Assignee: Industrial Technology Research InstituteInventors: Ching-Sheng Cho, Shinn-Jen Chang, Wan-Jung Teng, Jiun-Ji Chen
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Patent number: 6524657Abstract: 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: GrantFiled: May 7, 2002Date of Patent: February 25, 2003Assignee: Honeywell International Inc.Inventors: Oana M. Leonte, Tadashi Nakano, Kelly M. Beres, Kreisler Lau
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Publication number: 20020183476Abstract: 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: ApplicationFiled: May 7, 2002Publication date: December 5, 2002Applicant: Honeywell International Inc.Inventors: Oana M. Leonte, Tadashi Nakano, Kelly M. Beres, Kreisler Lau
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Patent number: 6303733Abstract: 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: GrantFiled: November 20, 1998Date of Patent: October 16, 2001Assignee: AlliedSignal Inc.Inventors: Kreisler S. Y. Lau, Tian-An Chen, Boris A. Korolev, Emma Brouk
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Patent number: 6291628Abstract: 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: GrantFiled: January 21, 1999Date of Patent: September 18, 2001Assignee: Allied Signal Inc.Inventors: Tian-An Chen, Kreisler S. Y. Lau, Qiang Zhao
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Patent number: 6124421Abstract: 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: GrantFiled: December 12, 1997Date of Patent: September 26, 2000Assignee: AlliedSignal Inc.Inventors: Kreisler S. Y. Lau, Tian-An Chen, Boris A. Korolev, Emma Brouk, Paul E. Schilling, Heike W. Thompson
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Patent number: 6040416Abstract: 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: GrantFiled: February 18, 1999Date of Patent: March 21, 2000Assignees: Johnson & Johnson Vision Products, Inc., Virginia Tech Intellectual Properties, Inc.Inventors: Venkateshwaran N. Sekharipuram, Beverly Sue Mecham, Atul Bhatnagar, James E. McGrath
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Patent number: 5914388Abstract: 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: GrantFiled: August 22, 1997Date of Patent: June 22, 1999Assignee: The Penn State Research FoundationInventors: 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
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Patent number: 5898062Abstract: 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: GrantFiled: April 10, 1997Date of Patent: April 27, 1999Assignee: The Penn State Research FoundationInventors: Harry R. Allcock, Archel M. A. Ambrosio
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Patent number: 5698664Abstract: 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: GrantFiled: April 26, 1995Date of Patent: December 16, 1997Assignees: The Penn State Research Foundation, University of TorontoInventors: Harry R. Allcock, Christopher T. Morrissey, Ian Manners, Charles H. Honeyman
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Patent number: 5548060Abstract: 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: GrantFiled: August 8, 1994Date of Patent: August 20, 1996Assignee: Penn State Research Foundation, Inc.Inventors: Harry R. Allcock, Eric H. Klingenberg, Mark P. Weller
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Patent number: 5464932Abstract: 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: GrantFiled: April 15, 1994Date of Patent: November 7, 1995Assignee: The Penn State Research FoundationInventors: Harry R. Allcock, Charles G. Cameron, Dawn E. Smith
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Patent number: 5399654Abstract: 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: GrantFiled: October 21, 1993Date of Patent: March 21, 1995Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Young H. Ko, Seung D. Cho, Byung C. Jeon
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Patent number: 5384337Abstract: 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: GrantFiled: February 5, 1993Date of Patent: January 24, 1995Inventor: William D. Budinger
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Patent number: 5312890Abstract: 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: GrantFiled: April 22, 1993Date of Patent: May 17, 1994Assignee: General Electric CompanyInventor: Gary C. Davis
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Patent number: 5310855Abstract: 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: GrantFiled: November 13, 1992Date of Patent: May 10, 1994Assignee: Bayer AktiengesellschaftInventors: Klaus Walz, Udo Hendricks, Hans-Albert Ehlert, Fritz Lesszinsky
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Patent number: 5304625Abstract: 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: GrantFiled: February 19, 1993Date of Patent: April 19, 1994Assignee: The United States of America as represented by the Secretary of the NavyInventor: Teddy M. Keller
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Patent number: 5208318Abstract: 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: GrantFiled: March 15, 1991Date of Patent: May 4, 1993Inventor: Teddy M. Keller
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Patent number: 5194564Abstract: 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: GrantFiled: June 18, 1992Date of Patent: March 16, 1993Assignee: General Electric CompanyInventors: Gary C. Davis, Christianus A. A. Claesen, Erwin M. A. Gijzen
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Patent number: 5182356Abstract: 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: GrantFiled: January 24, 1991Date of Patent: January 26, 1993Assignee: The United States of America as represented by the United States National Aeronautics and Space AdministrationInventors: John W. Connell, Paul M. Hergenrother, Peter Wolf
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Patent number: 5145936Abstract: 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: GrantFiled: September 6, 1991Date of Patent: September 8, 1992Assignee: Raychem CorporationInventor: Frank Mercer
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Patent number: 5101002Abstract: 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: GrantFiled: September 24, 1990Date of Patent: March 31, 1992Assignee: Ethyl CorporationInventors: W. Dirk Klobucar, David M. Indyke
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Patent number: 5089534Abstract: 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: GrantFiled: March 23, 1990Date of Patent: February 18, 1992Assignee: The Dow Chemical CompanyInventors: Johan A. Thoen, Robert A. Sewell, Ulrich Muller
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Patent number: 5079333Abstract: 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: GrantFiled: July 13, 1990Date of Patent: January 7, 1992Assignee: Virginia Tech Intellectual Properties, Inc.Inventors: James E. McGrath, Carrington D. Smith
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Patent number: 5053451Abstract: 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: GrantFiled: January 19, 1990Date of Patent: October 1, 1991Assignee: The Pennsylvania Research CorporationInventors: Harry R. Allcock, Sukky Kwon