Material Is A Nitrogen-containing Compound Patents (Class 528/215)
  • Patent number: 10259762
    Abstract: A phenylene ether oligomer is prepared by a process that includes partially converting 2,6-dimethylphenol to 3,3?,5,5?-tetramethyl-4,4?-dihydroxybiphenyl and/or 3,3?,5,5?-tetramethyldiphenoquinone, converting the residual 2,6 dimethylphenol to poly(2,6-dimethyl-1,4-phenylene ether) and any 3,3?,5,5?-tetramethyl-4,4?-dihydroxybiphenyl to 3,3?,5,5?-tetramethyldiphenoquinone, and reacting the poly(2,6-dimethyl-1,4-phenylene ether) and 3,3?,5,5?-tetramethyldiphenoquinone to form the phenylene ether oligomer. The preparation can be conducted without isolation of intermediates.
    Type: Grant
    Filed: November 10, 2016
    Date of Patent: April 16, 2019
    Assignee: SABIC GLOBAL TECHNOLOGIES B.V.
    Inventors: Rajesh Chowdhury, Eylem Tarkin-Tas, Xuezhi Jin
  • Publication number: 20150141610
    Abstract: A process for producing polyphenylene ether involves to keep a combustible solvent at a gaseous concentration below the minimums of explosion, to keep oxygen gas supplied at a gaseous concentration below the limiting oxygen concentration (LOC) of the solvent, and to make use of a reactor having a rotary-sealed mixer sealed with magnetic rotary feedthroughs to prevent static electricity generated, and then to improve safety and yield thereof.
    Type: Application
    Filed: November 12, 2014
    Publication date: May 21, 2015
    Inventors: Dein-Run FUNG, Jung-Jen CHUANG, Yi-Cheng LI, Zhang-Jian HUANG
  • Patent number: 9018342
    Abstract: A poly(phenylene ether) copolymer comprises about 5 to 40 mole percent repeat units derived from 2-phenylphenol and 60 to about 95 mole percent repeat units derived from 2,6-dimethylphenol, wherein the poly(phenylene ether) copolymer has a weight average molecular weight of at least 8,000 atomic mass units, as measured by gel permeation chromatography. A method of preparing the poly(phenylene ether) copolymer, comprises oxidatively copolymerizing a monomer mixture comprising about 5 to 40 mole percent 2-phenylphenol and about 60 to about 95 mole percent 2,6-dimethylphenol in the presence of a solvent, molecular oxygen, and a polymerization catalyst comprising a metal ion and at least one amine ligand to form a solution of the poly(phenylene ether) copolymer in the solvent, wherein a ratio of total moles of 2-phenylphenol and 2,6-dimethylphenol to moles of metal ion is about 10:1 to about 1200:1.
    Type: Grant
    Filed: July 27, 2012
    Date of Patent: April 28, 2015
    Assignee: Sabic Global Technologies B.V.
    Inventors: Alvaro Carrillo, Scott Michael Fisher, Hua Guo, Stephan Moyses, Eylem Tarkin-Tas
  • Patent number: 9012572
    Abstract: A polyphenylene ether oligomer is provided. The polyphenylene ether oligomer has the following formula (I): X is ?R is H or C1-6 alkyl group; Y independently is a moiety polymerized by at least two different phenol-based compounds; and Z independently is H, acryloyl group, allyl group, vinylbenzyl group, epoxypropyl group, methylacryloyl group, propargyl group, or cyanoallyl group.
    Type: Grant
    Filed: December 26, 2013
    Date of Patent: April 21, 2015
    Assignee: Industrial Technology Research Institute
    Inventors: I-Hong Lin, Chung-Cheng Lin, Wei-Ta Yang, Chih-Hsiang Lin
  • Publication number: 20150038667
    Abstract: A poly(phenylene ether) copolymer comprising about 5 to 40 mole percent repeat units derived from 2-phenylphenol and 60 to about 95 mole percent repeat units derived from 2,6-dimethylphenol, wherein the poly(phenylene ether) copolymer has a weight average molecular weight of at least 8,000 atomic mass units, is disclosed. Also disclosed is a method of preparing the poly(phenylene ether) copolymer, the method comprising oxidatively copolymerizing a monomer mixture comprising about 5 to 40 mole percent 2-phenylphenol and about 60 to about 95 mole percent 2,6-dimethylphenol in the presence of a solvent, molecular oxygen, and a polymerization catalyst comprising a metal ion and at least one amine ligand to form a solution of the poly(phenylene ether) copolymer in the solvent, wherein a ratio of total moles of 2-phenylphenol and 2,6-dimethylphenol to moles of metal ion is about 10:1 to about 1200:1.
    Type: Application
    Filed: July 27, 2012
    Publication date: February 5, 2015
    Applicant: SABIC INNOVATIVE PLASTICS IP B.V.
    Inventors: Alvaro Carrillo, Scott Michael Fisher, Hua Guo, Stephan Moyses, Eylem Tarkin-Tas
  • Publication number: 20130245182
    Abstract: An object of the present invention is to provide a polyphenylene ether powder that has a high loose apparent specific gravity and good handleability, as well as a high solvent solubility, and good covering properties by coating, applying and the like, and further, when formed as a covering film, providing the covering film with excellent mechanical properties. The polyphenylene ether powder according to the present invention has a loose apparent specific gravity of 0.40 or more and 0.85 or less, and includes 5 to 20 mass % of a component having a molecular weight of 50,000 or more and 12 to 30 mass % of a component having a molecular weight of 8,000 or less.
    Type: Application
    Filed: October 12, 2011
    Publication date: September 19, 2013
    Applicant: ASAHI KASEI CHEMICALS CORPORATION
    Inventor: Tomohiro Kondo
  • Patent number: 8404798
    Abstract: Polyarylene ether is polymerized using a dissolving agent including anisole, wherein the polyarylene ether includes about 1 to about 3,000 ppm of anisole.
    Type: Grant
    Filed: December 13, 2011
    Date of Patent: March 26, 2013
    Assignee: Cheil Industries Inc.
    Inventors: Yong Tae Kim, Jin Kyu Kim, Bok Nam Jang, Joong In Kim, Young Jun Kim, Ji Heung Kim, Chang Jae Lee
  • Publication number: 20120309927
    Abstract: Polyarylene ether is polymerized using a dissolving agent including anisole, wherein the polyarylene ether includes about 1 to about 3,000 ppm of anisole.
    Type: Application
    Filed: December 13, 2011
    Publication date: December 6, 2012
    Applicant: CHEIL INDUSTRIES INC.
    Inventors: Yong Tae KIM, Jin Kyu KIM, Bok Nam JANG, Joong In KIM, Young Jun KIM, Ji Heung KIM, Chang Jae LEE
  • Patent number: 8288501
    Abstract: Method for producing polyphenylene ether, comprising preparing a polymerization solution of 10-25 parts by mass of a phenolic compound (M) and 75-90 parts by mass of an aromatic solvent (A) with the total of the compound and the solvent being 100 parts by mass, and 0.1-10 parts by mass of a catalyst (C) containing a metal salt; performing oxidative polymerization of the phenolic compound (M) by passing oxygen-containing gas through polymerization solution; stopping polymerization by mixing aqueous chelating agent solution into polymerization solution; subjecting a diphenoquinone compound produced as a by-product to quinone binding process or removal by reduction; and obtaining polyphenylene ether by separating aqueous phase through liquid-liquid separation. In the method for producing a polyphenylene ether, 0.001-0.004 part by weight of an ion catalyst (D) is added into the polymerization solution before the liquid-liquid separation.
    Type: Grant
    Filed: February 15, 2012
    Date of Patent: October 16, 2012
    Assignee: Asahi Kasei Chemicals Corporation
    Inventors: Mutsumi Maeda, Hiroaki Furukawa
  • Publication number: 20120149865
    Abstract: Method for producing polyphenylene ether, comprising preparing a polymerization solution of 10-25 parts by mass of a phenolic compound (M) and 75-90 parts by mass of an aromatic solvent (A) with the total of the compound and the solvent being 100 parts by mass, and 0.1-10 parts by mass of a catalyst (C) containing a metal salt; performing oxidative polymerization of the phenolic compound (M) by passing oxygen-containing gas through polymerization solution; stopping polymerization by mixing aqueous chelating agent solution into polymerization solution; subjecting a diphenoquinone compound produced as a by-product to quinone binding process or removal by reduction; and obtaining polyphenylene ether by separating aqueous phase through liquid-liquid separation. In the method for producing a polyphenylene ether, 0.001-0.004 part by weight of an ion catalyst (D) is added into the polymerization solution before the liquid-liquid separation.
    Type: Application
    Filed: February 15, 2012
    Publication date: June 14, 2012
    Applicant: ASAHI KASEI CHEMICALS CORPORATION
    Inventors: Mutsumi MAEDA, Hiroaki FURUKAWA
  • Patent number: 8133933
    Abstract: Phenolic resin binder systems for sand molds, used in metal casting, which improve the quality of thermally reclaimed sand, are described. The substantial or complete elimination of calcium compounds (e.g., calcium stearate and calcium hydroxide, conventionally employed as a mold lubricant and a resin curing catalyst, respectively) allows the thermally reclaimed sand to be reused over multiple thermal reclamation cycles without the adverse effects previously encountered.
    Type: Grant
    Filed: August 11, 2006
    Date of Patent: March 13, 2012
    Assignee: Georgia-Pacific Chemicals LLC
    Inventors: Richard Rediger, Edward Lucas
  • Publication number: 20110288262
    Abstract: A poly(2,6-dimethyl-1,4-phenylene ether) having a high molecular weight and a reduced content of low molecular weight species can be prepared by a method that includes specific conditions for the oxidative polymerization, chelation, and isolation steps. The poly(2,6-dimethyl-1,4-phenylene ether) is particularly useful for the fabrication of fluid separation membranes.
    Type: Application
    Filed: August 8, 2011
    Publication date: November 24, 2011
    Inventors: Erik René Delsman, Gert-Jan Schoenmakers
  • Publication number: 20090247724
    Abstract: A poly(arylene ether) copolymer is the product of oxidative copolymerization of monomers including a monohydric phenol and a dihydric phenol. It has an intrinsic viscosity of about 0.04 to about 0.15 deciliter per gram and, on average, about 1.8 to about 2 hydroxyl groups per molecule. The poly(arylene ether) copolymer is enriched in low molecular weight copolymer chains and copolymer chains that include a terminal unit derived from the dihydric phenol.
    Type: Application
    Filed: March 31, 2009
    Publication date: October 1, 2009
    Inventors: Alvaro Carrillo, Erik Rene Delsman, Hua Guo, Alexey Kruglov, Edward N. Peters
  • Patent number: 7282534
    Abstract: A resin composition comprising a polyphenylene ether produced by polymerizing a monomer component consisting of 100 parts by weight of 2,6-dimethylphenol and 0.5 to 7.5 parts by weight of o-cresol in the presence of both a catalyst and an oxygen-containing gas and a flame retardant. When the polyphenylene ether has a molecular weight distribution of 2.8 to 8.0, the resulting resin composition is more excellent in flame retardance, particularly anti-dripping properties in burning. The resin composition is applicable to not only electric and electronic applications necessitating high flame retardance but also other fields of application of polyphenylene ether resins.
    Type: Grant
    Filed: July 15, 2003
    Date of Patent: October 16, 2007
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventors: Teruaki Sakuma, Akira Mitsui
  • Patent number: 7060781
    Abstract: A 2,6-dimethylphenol composition having an m-cresol content of from 15 to 700 ppm on a weight basis has effects of drastically improving polymerization activity and particularly, improving the color tone of polyphenylene ethers. Therefore, the composition makes it possible to provide a preparation process having improved productivity, and at the same time, provide polyphenylene ethers having good quality.
    Type: Grant
    Filed: August 6, 2002
    Date of Patent: June 13, 2006
    Assignee: Asahi Kasei Chemicals Corporation
    Inventors: Akira Mitsui, Osamu Shoji, Hitoshi Ota
  • Patent number: 7049388
    Abstract: A process for manufacturing an ?-dihydroxy derivative from an aryl allyl ether wherein such ?-dihydroxy derivative can be used to prepare an ?-halohydrin intermediate and an epoxy resin prepared therefrom including epoxidizing an ?-halohydrin intermediate produced from a halide substitution of an ?-dihydroxy derivative which has been obtained by a dihydroxylation reaction of an aryl allyl ether in the presence of an oxidant or in the presence of an oxidant and a catalyst.
    Type: Grant
    Filed: September 9, 2003
    Date of Patent: May 23, 2006
    Assignee: Dow Global Technologies Inc.
    Inventors: Clinton J. Boriack, Zeng K. Liao, Thomas H. Kalantar
  • Patent number: 6646102
    Abstract: A process for manufacturing an &agr;-dihydroxy derivative from an aryl allyl ether wherein such &agr;-dihydroxy derivative can be used to prepare an &agr;-halohydrin intermediate and an epoxy resin prepared therefrom including epoxidizing an &agr;-halohydrin intermediate produced from a halide substitution of an &agr;-dihydroxy derivative which has been obtained by a dihydroxylation reaction of an aryl allyl ether in the presence of an oxidant or in the presence of an oxidant and a catalyst.
    Type: Grant
    Filed: July 5, 2001
    Date of Patent: November 11, 2003
    Assignee: Dow Global Technologies Inc.
    Inventors: Clinton J. Boriack, Zeng K. Liao, Thomas H. Kalantar
  • Patent number: 6521735
    Abstract: A process for producing a polyphenylene ether by oxidative polymerization of a phenol compound using a catalyst and an oxygen-containing gas, wherein said catalyst comprises a copper compound, a bromine compound, a diamine compound of formula (1) as recited in the specification, a tertiary monoamine compound and a secondary monoamine compound, and wherein said process comprises the steps of: preparing a catalyst component (P1) in a container which is under a substantially oxygen-free inert atmosphere by mixing the copper compound and the bromine compound to obtain a mixture and then mixing the mixture with the secondary monoamine compound in an amount of at least 2 times the molar amount of the copper atom; separately preparing a catalyst component (P2) by mixing the diamine compound of formula (1) and the tertiary monoamine compound together with a solvent in an oxidative polymerization vessel; adding a predetermined amount of the catalyst component (P1) to the polymerization vessel containing the catalyst c
    Type: Grant
    Filed: June 19, 2001
    Date of Patent: February 18, 2003
    Assignees: Asahi Kasei Kabushiki Kaisha, Mitsubishi Gas Chemical Company, Inc.
    Inventors: Akira Mitsui, Yuji Takeda
  • Patent number: 6489439
    Abstract: A process for producing a polyphenylene ether by oxidative polymerization of a phenol compound using a catalyst and an oxygen-containing gas, wherein the catalyst comprises a copper compound, a bromine compound, a diamine compound represented by the following formula (1): (wherein, R1, R2, R3 and R4 each independently represents hydrogen or a C1-6 linear or branched alkyl group with the proviso that all of them do not represent hydrogen simultaneously, and R5 represents a linear or methyl-branched C2-5 alkylene group), a tertiary monoamine compound and a secondary monoamine compound, wherein the process comprises the steps of: controlling an absolute pressure at a gaseous phase of a reaction vessel to a range of from 0.098 MPa to less than 0.392 MPa; and feeding the oxygen-containing gas to the reaction vessel, the oxygen-containing gas having an oxygen partial pressure, in terms of an absolute pressure, of from 0.0147 MPa to 0.0883 MPa.
    Type: Grant
    Filed: June 19, 2001
    Date of Patent: December 3, 2002
    Assignees: Asahi Kasei Kabushiki Kaisha, Mitsubishi Gas Chemical Company, Inc.
    Inventors: Akira Mitsui, Yuji Takeda
  • Patent number: 6472499
    Abstract: Poly(arylene ether) resins having intrinsic viscosities greater than about 0.8 dL/g are produced in the reaction of a phenol with oxygen in the presence of an organic solvent and a metal complex catalyst, the phenol concentration being about 5 to about 15 weight percent of the sum of phenol and solvent, and the molar ratio of metal in the metal complex catalyst to the phenol being about 1:100 to about 1:200.
    Type: Grant
    Filed: August 4, 2000
    Date of Patent: October 29, 2002
    Assignee: General Electric Company
    Inventors: Adrianus J. F. M. Braat, Hugo G. E. Ingelbrecht
  • Publication number: 20020095020
    Abstract: An improvement to the melt transesterification reaction of diaryl carbonate with dihydroxy aryl compound is disclosed.
    Type: Application
    Filed: January 2, 2002
    Publication date: July 18, 2002
    Inventors: Uwe Hucks, Kaspar Hallenberger, Silke Kratschmer, Michael Prein, Steffen Kuhling
  • Patent number: 6417274
    Abstract: The invention relates to a novel process for preparing functionalized PPE, the process comprising oxidative coupling in a reaction solution at least one monovalent phenol species using an oxygen containing gas and a complex metal catalyst to produce a PPE; and functionalizing the PPE prior to and/or during at least one isolation step for devolatilization of the reaction solvent. The invention also relates to the polyphenylene ether resin made by the process as well as blends and articles containing the polyphenylene ether resin made by the process.
    Type: Grant
    Filed: February 5, 1999
    Date of Patent: July 9, 2002
    Assignee: General Electric Co.
    Inventors: Adrianus J. F. M. Braat, Rene de Jongh, Juraj Liska
  • Patent number: 6362314
    Abstract: A process of controlling the molecular weight and dispersity of poly(p-ethylphenol) and poly(m-cresol) synthesized enzymatically by varying the composition of the reaction medium. Polymers with low dispersities and molecular weights from 1000 to 3000 are synthesized in reversed micelles and biphasic systems. In comparison, reactions in bulk solvents resulted in a narrow range of molecular weights (281 to 675 with poly(p-ethylphenol) in a DMF/water system and 1,400 to 25,000 with poly(m-cresol) in an ethanol/water system). Poly(p-ethylphenol) was functionalized at hydroxyl positions with palmitoyl, cinnamoyl, and biotin groups.
    Type: Grant
    Filed: February 4, 1999
    Date of Patent: March 26, 2002
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventors: Joseph A. Akkara, David L. Kaplan, Madhu Ayyagari
  • Patent number: 6362315
    Abstract: A process of controlling the molecular weight and dispersity of poly(p-ethylphenol) and poly(m-cresol) synthesized enzymatically by varying the composition of the reaction medium. Polymers with low dispersities and molecular weights from 1000 to 3000 are synthesized in reversed micelles and biphasic systems. In comparison, reactions in bulk solvents resulted in a narrow range of molecular weights (281 to 675 with poly(p-ethylphenol) in a DMF/water system and 1,400 to 25,000 with poly(m-cresol) in an ethanol/water system). Poly(p-ethylphenol) was functionalized at hydroxyl positions with palmitoyl, cinnamoyl, and biotin groups.
    Type: Grant
    Filed: February 4, 1999
    Date of Patent: March 26, 2002
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventors: Joseph A. Akkara, David L. Kaplan, Madhu Ayyagari
  • Publication number: 20020013446
    Abstract: A process for producing a polyphenylene ether by oxidative polymerization of a phenol compound using a catalyst and an oxygen-containing gas, wherein said catalyst comprises a copper compound, a bromine compound, a diamine compound of formula (1) as recited in the specification, a tertiary monoamine compound and a secondary monoamine compound, and wherein said process comprises the steps of: preparing a catalyst component (P1) in a container which is under a substantially oxygen-free inert atmosphere by mixing the copper compound and the bromine compound to obtain a mixture and then mixing the mixture with the secondary monoamine compound in an amount of at least 2 times the molar amount of the copper atom; separately preparing a catalyst component (P2) by mixing the diamine compound of formula (1) and the tertiary monoamine compound together with a solvent in an oxidative polymerization vessel; adding a predetermined amount of the catalyst component (P1) to the polymerization vessel containing the catalyst c
    Type: Application
    Filed: June 19, 2001
    Publication date: January 31, 2002
    Inventors: Akira Mitsui, Yuji Takeda
  • Publication number: 20020010314
    Abstract: A process for producing a polyphenylene ether by oxidative polymerization of a phenol compound using a catalyst and an oxygen-containing gas, wherein the catalyst comprises a copper compound, a bromine compound, a diamine compound represented by the following formula (1): 1
    Type: Application
    Filed: June 19, 2001
    Publication date: January 24, 2002
    Inventors: Akira Mitsui, Yuji Takeda
  • Patent number: 6307010
    Abstract: The invention relates to a novel process for the manufacture of functionalized polyphenylene ether resins through redistribution with a functionalized phenolic compound in the polyphenylene ether resin polymerization reaction solution without the addition of an added redistribution catalyst or promoter. The invention also relates to the functionalized polyphenylene ether resin made by the process as well as blends and articles containing the functionalized polyphenylene ether resin made by the process.
    Type: Grant
    Filed: February 5, 1999
    Date of Patent: October 23, 2001
    Assignee: General Electric Company
    Inventors: Adrianus J. F. M. Braat, Hugo G. E. Engelbrecht, Juraj Liska
  • Patent number: 6284863
    Abstract: A polymer having an O-substituted vinylphenol unit represented by the following formula (I) wherein R1, R2 and R3 represent an alkyl; or R1 and R2, R1 and R3 or R2 and R3 are bound together and respectively form an alkylene; or R2 is methylidyne wherein one bond in the methylidyne is bound to R1, the other bond is bound to R3, and R1 and R3 represent alkylene, and a resist composition comprising the polymer are provided.
    Type: Grant
    Filed: April 28, 2000
    Date of Patent: September 4, 2001
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Yoshiteru Ohta, Sang-tae Kim, Masumi Suetsugu
  • Patent number: 6265521
    Abstract: Polyether polymers such as polyetherimides are prepared by a two-step reaction. The first step is the reaction between an alkali metal salt of a dihydroxy-substituted aromatic hydrocarbon, such as bisphenol A disodium salt, and a substituted aromatic compound such as 1,3-bis[N-(4-chlorophthalimido)]benzene, the alkali metal salt being employed in an amount less than stoichiometric. The intermediate low molecular weight polymer thus produced then undergoes reaction with additional alkali metal salt. By this method, a polyether polymer of closely controlled molecular weight can be conveniently prepared.
    Type: Grant
    Filed: August 7, 2000
    Date of Patent: July 24, 2001
    Assignee: General Electric Company
    Inventors: Thomas Joseph Fyvie, Peter David Phelps, Paul Edward Howson, Donald Frank Rohr, Ganesh Kailasam, Elliott West Shanklin
  • Publication number: 20010003774
    Abstract: A process of controlling the molecular weight and dispersity of poly(p-ethylphenol) and poly(m-cresol) synthesized enzymatically by varying the composition of the reaction medium. Polymers with low dispersities and molecular weights from 1000 to 3000 are synthesized in reversed micelles and biphasic systems. In comparison, reactions in bulk solvents resulted in a narrow range of molecular weights (281 to 675 with poly(p-ethylphenol) in a DMF/water system and 1,400 to 25,000 with poly(m-cresol) in an ethanol/water system). Poly(p-ethylphenol) was functionalized at hydroxyl positions with palmitoyl, cinnamoyl, and biotin groups.
    Type: Application
    Filed: February 4, 1999
    Publication date: June 14, 2001
    Inventors: JOSEPH A. AKKARA, DAVID L. KAPLAN, MADHO AYYAGARI
  • Publication number: 20010002417
    Abstract: A process of controlling the molecular weight and dispersity of poly(p-ethylphenol) and poly(n-cresol) synthesized enzymatically by varying the composition of the reaction medium. Polymers with low dispersities and molecular weights from 1000 to 3000 are synthesized in reversed micelles and biphasic systems. In comparison, reactions in bulk solvents resulted in a narrow range of molecular weights (281 to 675 with poly(p-ethylphenol) in a DMF/water system and 1,400 to 25,000 with poly(m-cresol) in an ethanol/water system). Poly(p-ethylphenol) was functionalized at hydroxyl positions with palmitoyl, cinnamoyl, and biotin groups.
    Type: Application
    Filed: February 4, 1999
    Publication date: May 31, 2001
    Inventors: JOSEPH A. AKKARA, DAVID L. KAPLAN, MADHU AYYAGARI
  • Patent number: 6096859
    Abstract: A process of controlling the molecular weight and dispersity of poly(p-ethylphenol) and poly(m-cresol) synthesized enzymatically by varying the composition of the reaction medium. Polymers with low dispersities and molecular weights from 1000 to 3000 are synthesized in reversed micelles and biphasic systems. In comparison, reactions in bulk solvents resulted in a narrow range of molecular weights (281 to 675 with poly(p-ethylphenol) in a DMF/water system and 1,400 to 25,000 with poly(m-cresol) in an ethanol/water system). Poly(p-ethylphenol) was functionalized at hydroxyl positions with palmitoyl, cinnamoyl, and biotin groups.
    Type: Grant
    Filed: January 16, 1996
    Date of Patent: August 1, 2000
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventors: Joseph A. Akkara, David L. Kaplan, Madhu Ayyagari
  • Patent number: 5908915
    Abstract: Copolyetherimides are prepared by the reaction of an alkali metal salt of a dihydroxyaromatic compound with a bis(substituted phthalimide) and a third compound which may be a substituted aromatic ketone or sulfone or a macrocyclic polycarbonate or polyarylate oligomer. The reaction takes place the in presence of a solvent and a phase transfer catalyst having high thermal stability, such as a hexaalkylguanidinium halide. Random or block copolymers may be obtained, depending on the reaction conditions.
    Type: Grant
    Filed: October 6, 1997
    Date of Patent: June 1, 1999
    Assignee: General Electric Company
    Inventor: Daniel Joseph Brunelle
  • 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: 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: 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: 5726321
    Abstract: Process for carrying out gas/liquid reactions at from (-50.degree.) to 300.degree. C. and from 0.1 to 100 bar by carrying out the reaction in the absence of a continuous gas phase, and, as a special case, a process for the batchwise reaction of acetylene in the liquid phase at from 0.degree. to 300.degree. C. and from 2 to 30 bar, in which acetylene is introduced a) in the absence of a continuous gas phase and b) under isobaric conditions to a degree of saturation of from 5 to 100%.
    Type: Grant
    Filed: March 22, 1996
    Date of Patent: March 10, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Bittins, Marc Heider, Martin Schmidt-Radde, Jochen Kellenbenz, Kurt Josef Wagner, Peter Zehner, Stefan Berg
  • Patent number: 5693742
    Abstract: A method for making polyarylene ethers comprises the step of melt polymerizing phenolic monomers in the presence of oxygen and oxidative coupling catalysts without employing environmentally unfriendly solvents.
    Type: Grant
    Filed: September 15, 1995
    Date of Patent: December 2, 1997
    Assignee: General Electric Company
    Inventors: Dwain Montgomery White, Margaret Louise Blohm, David Winfield Woodruff, Sterling Bruce Brown
  • Patent number: 5659006
    Abstract: A method for making polyarylene ethers comprising the step of melt polymerizing 2,6-disubstituted-4-alkylphenols in the presence of an oxidative coupling catalyst and in the absence of environmentally unfriendly solvents.
    Type: Grant
    Filed: December 14, 1995
    Date of Patent: August 19, 1997
    Assignee: General Electric Company
    Inventor: Dwain M. White
  • 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: 5629405
    Abstract: A method for making polyarylene ethers is described and the method comprises the step of polymerizing hydroxyaromatic monomers or oligomers prepared therefrom in the presence of pyridine catalysts.
    Type: Grant
    Filed: November 20, 1995
    Date of Patent: May 13, 1997
    Assignee: General Electric Company
    Inventor: Dwain M. White
  • 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: 5621066
    Abstract: An environmentally friendly process is provided for the preparation of poly(phenylene ether) resin by oxidatively coupling at least one monovalent phenol using an oxygen containing gas and a complex copper (I) amine catalyst as the oxidizing agent and extracting the copper catalyst with an aqueous containing solution as a copper (II)-organic acid salt, an improvement which comprises reduction and recovery of the copper (II) species as a copper (I) species for regeneration of the complex copper (I) amine catalyst.
    Type: Grant
    Filed: August 10, 1994
    Date of Patent: April 15, 1997
    Assignee: General Electric Company
    Inventor: Jilles J. H. Edema
  • Patent number: 5571887
    Abstract: A new thermoplastic homopolymer of o-cresol which is a poly(2-methylphenylene oxide) having a high molecular weight distribution is described. The polymer is prepared using a 2 and/or 6 substituted pyridine catalyst to the molecular weight distribution. The homopolymer can be blended with other thermoplastic polymers. The homopolymer is rapidly biodegraded, particularly in soil containing soil microorganisms.
    Type: Grant
    Filed: June 19, 1995
    Date of Patent: November 5, 1996
    Assignee: Board of Trustees operating Michigan State University
    Inventors: Li-Xia Li, Patrick J. Oriel, Eric A. Grulke
  • Patent number: 5563300
    Abstract: The present invention provides a unique and novel way of producing carbinols such as 4-hydroxyphenylmethylcarbinol (HPMC). In this new process, a ketone such as 4-hydroxyacetophenone (4-HAP) is heated under suitable hydrogenation conditions of temperature and pressure in the presence of a suitable catalyst and a basic material, and for a sufficient period of time to form HPMC.
    Type: Grant
    Filed: December 7, 1995
    Date of Patent: October 8, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: James R. Sounik, Graham N. Mott, Charles B. Hilton, Mohammad Aslam
  • 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: 5554719
    Abstract: A new polyhydroxystyrene having a novolak type structure which is prepared by the process 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 polyhydroxystyrene.
    Type: Grant
    Filed: June 16, 1995
    Date of Patent: September 10, 1996
    Assignee: Hoechst Celanese Corporation
    Inventor: James R. Sounik
  • Patent number: 5523378
    Abstract: The present invention provides a unique and novel way of producing polyhydroxystyrene which comprises the steps of (a) heating 4-hydroxyacetophenone under suitable hydrogenation conditions of temperature and pressure in the presence of a suitable palladium catalyst and a basic material and for a sufficient period of time to form 4-hydroxyphenylmethylcarbinol; (b) heating 4-hydroxyphenylmethylcarbinol under suitable conditions of temperature and pressure and for a sufficient period of time to form said polyhydroxystyrene.
    Type: Grant
    Filed: September 18, 1995
    Date of Patent: June 4, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: James R. Sounik, Graham N. Mott, Charles B. Hilton
  • Patent number: 5459173
    Abstract: Stable thiol-ene compositions are provided which comprise a polythiol, a polyene and a stabilizer system comprising an alkenyl substituted phenolic compound having a formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are independently selected from the group consisting of H, OR, a C.sub.1 -C.sub.8 alkyl, substituted alkyl, alkenyl or substituted alkenyl, a C.sub.6 -C.sub.20 aryl or substituted aryl, or a cyano group; R.sup.4 is H, R, OR, halogen, COR, COOR, or SR; R.sup.5 is OH, OR, OCOR, OCOOR, OCONHR, or OTMS; R is a C.sub.1 -C.sub.6 alkyl, a cycloalkyl, or a C.sub.6 -C.sub.20 caryl or substituted aryl; x and y are 1, 2, or 3; z is 0, 1, or 2; and x+y+z=2, 3, or 4; or a formula: ##STR2## where x, y, z, w, R.sup.1 R.sup.2 R.sup.3, R.sup.4 and R.sup.5 are defined as above, except that x+y+z=2-6, and R.sup.6 is CH.sub.2, C(CH.sub.3).sub.2, O, S, or SO.sub.
    Type: Grant
    Filed: June 22, 1993
    Date of Patent: October 17, 1995
    Assignee: Loctite Corporation
    Inventors: David M. Glaser, Anthony F. Jacobine, Paul J. Grabek