Patents by Inventor Paul Michael Smigelski, Jr.

Paul Michael Smigelski, Jr. has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 6870025
    Abstract: Polycarbonates containing low or undetectable levels of Fries rearrangement products and comprising repeat units derived from one or more of resorcinol, hydroquinone, methylhydroquinone, bisphenol A, and 4,4?-biphenol have been prepared by the melt reaction of one or more of the aforementioned dihydroxy aromatic compounds with an ester-substituted diaryl carbonate such as bis-methyl salicyl carbonate. Low, or in many instances undetectable, levels of Fries rearrangement products are found in the product polycarbonates obtained as the combined result of a highly effective catalyst system which suppresses the Fries reaction and the use of lower melt polymerization temperatures relative to temperatures required for the analogous polymerization reactions using diphenyl carbonate.
    Type: Grant
    Filed: December 23, 2002
    Date of Patent: March 22, 2005
    Assignee: General Electric Company
    Inventors: Patrick Joseph McCloskey, Jan Pleun Lens, James Anthony Cella, Jan Henk Kamps, Kathryn Lynn Longley, Narayan Ramesh, Warren William Reilly, Paul Michael Smigelski, Jr., Marc Brian Wisnudel
  • Patent number: 6790929
    Abstract: This invention relates to an extrusion method preparing polycarbonates from a solution of an oligomeric polycarbonate. A mixture of bis(methyl salicyl)carbonate (BMSC), BPA and a transesterification catalyst are first equilibrated at moderate temperatures to provide a solution of polycarbonate oligomer in methyl salicylate. The solution is then fed to a devolatilizing extruder, where the polymerization reaction is completed and the methyl salicylate solvent is removed. The solution comprising the oligomeric polycarbonate can also be pre-heated under pressure to a temperature above the boiling point of methyl salicylate and subsequently fed to a devolatilizing extruder equipped for rapid flashing off the solvent. The method provides polycarbonate with greater efficiency than the corresponding process in which unreacted monomers are fed to the extruder. Additionally, the method of the invention does not require the isolation of a precursor polycarbonate comprising ester-substituted phenoxy terminal groups.
    Type: Grant
    Filed: March 17, 2003
    Date of Patent: September 14, 2004
    Assignee: General Electric Company
    Inventors: Norberto Silvi, Mark Howard Giammattei, Patrick Joseph McCloskey, Alberto Nisoli, James Day, Narayan Ramesh, Paul Michael Smigelski, Jr., Paul Russell Wilson
  • Patent number: 6576801
    Abstract: The present invention relates to a method of neutralizing residual acid species in crude dihydric phenol comprising the step of introducing a thermally stable organic base selected from the group consisting of tetraalkyl phosphonium hydroxides, tetraorganophosphonium carboxylic acid salts, or a mixture thereof into the crude dihydric phenol.
    Type: Grant
    Filed: February 25, 2002
    Date of Patent: June 10, 2003
    Assignee: General Electric Company
    Inventors: Paul Michael Smigelski, Jr., Timothy Brydon Burnell, Patrick Joseph McCloskey
  • Patent number: 6548623
    Abstract: Polycarbonates containing low or undetectable levels of Fries rearrangement product may be prepared by the melt reaction of a dihydroxy aromatic compound such as bisphenol A with an ester-substituted diaryl carbonate such as the diaryl carbonate of methyl salicylate, bis-methyl salicyl carbonate. Low levels of Fries product are obtained as the combined result of a highly effective catalyst system which suppresses the Fries reaction and the use of lower melt polymerization temperatures relative to temperatures required for the analogous polymerization reaction using diphenyl carbonate.
    Type: Grant
    Filed: July 24, 2001
    Date of Patent: April 15, 2003
    Assignee: General Electric Company
    Inventors: Daniel Joseph Brunelle, Patrick Joseph McCloskey, Paul Michael Smigelski, Jr., Timothy Brydon Burnell, Ganesh Kailasam
  • Patent number: 6518391
    Abstract: Solid state polymerization of partially crystalline polycarbonate oligomers bearing ester-substituted terminal groups occurs at useful reaction rates despite their high level of endcapping. Partially crystalline polycarbonate oligomers having ester substituted terminal groups may be obtained in a single step by reaction of an ester substituted diaryl carbonate such as bis-methyl salicyl carbonate with a dihydroxy aromatic compound such as bisphenol A in the presence of a transesterification catalyst such as sodium hydroxide. Alternatively, amorphous oligomeric polycarbonates incorporating ester substituted endgroups may be obtained through careful control of the melt reaction conditions. The amorphous oligomeric polycarbonates are crystallized upon exposure to solvent vapor and subsequently undergo solid state polymerization at synthetically useful reaction rates.
    Type: Grant
    Filed: July 24, 2001
    Date of Patent: February 11, 2003
    Assignee: General Electric Company
    Inventors: Patrick Joseph McCloskey, James Day, Paul Michael Smigelski, Jr., Timothy Brydon Burnell
  • Patent number: 6500914
    Abstract: A method for end-capping polycarbonate resins, comprising the step of processing a mixture comprising a polycarbonate having free hydroxyl-end groups and an end-capping reagent in a melt transesterification reaction to produce a polycarbonate resin, wherein the end-capping reagent comprises a mixture of:(a) at least one species of a symmetrical activated aromatic carbonate, and (b) at least one species of a symmetrical non-activated aromatic carbonate, whereby said end-capping reagent reacts with at least some of the free hydroxyl end-groups of the polycarbonate to produce an end-capped polycarbonate resin.
    Type: Grant
    Filed: October 10, 2001
    Date of Patent: December 31, 2002
    Assignee: General Electric Company
    Inventors: Hans Peter Brack, James Anthony Cella, Dennis Karlik, Paul Michael Smigelski, Jr.
  • Patent number: 6420588
    Abstract: High yields of ester-substituted diary carbonates such as bis-methyl salicyl carbonate were obtained by the condensation of methyl salicylate with phosgene in the presence of a phase transfer catalyst (PTC) in an interfacial reaction system in which the pH of the aqueous phase was greater than 9.3. Using the method of the present invention conversions of greater than 99% were obtained whereas under standard conditions using triethylamine as the catalyst conversions were limited to 70-75% of the methyl salicylate starting material even with a 20 mole % excess of added phosgene. The optimized conditions of the of the present invention use only a slight excess of phosgene and represent an attractive route for the manufacture of bis methyl salicyl carbonate and ester-substituted diaryl carbonates generally.
    Type: Grant
    Filed: July 24, 2001
    Date of Patent: July 16, 2002
    Assignee: General Electric Company
    Inventors: Patrick Joseph McCloskey, Timothy Brydon Burnell, Daniel Joseph Brunelle, Elliott West Shanklin, Paul Michael Smigelski, Jr., Ganesh Kailasam
  • Patent number: 6414106
    Abstract: The present invention relates to a method of neutralizing residual acid species in crude dihydric phenol comprising the step of introducing a thermally stable organic base selected from the group consisting of tetraalkyl phosphonium hydroxides, tetraorganophosphonium carboxylic acid salts, or a mixture thereof into the crude dihydric phenol.
    Type: Grant
    Filed: March 2, 2001
    Date of Patent: July 2, 2002
    Assignee: General Electric Company
    Inventors: Paul Michael Smigelski, Jr., Timothy Brydon Burnell, Patrick Joseph McCloskey
  • Patent number: 6403754
    Abstract: Acidic impurities in dihydroxyaromatic compounds such as bisphenol A, as illustrated by sulfonic acids and mercaptocarboxylic acids, can have an adverse effect on the molecular weight of a polycarbonate prepared therefrom by transesterification. The same is true of acidic impurities in diaryl carbonates such as diphenyl carbonate, as illustrated by salicylic acid and ferric chloride. The reagents are analyzed for these impurities. Based on the analysis, the reagents are discarded or recycled, or a compensatory amount of alkali metal hydroxide is employed as a catalyst in the reaction.
    Type: Grant
    Filed: January 29, 2001
    Date of Patent: June 11, 2002
    Assignee: General Electric Company
    Inventors: Patrick Joseph McCloskey, Paul Michael Smigelski, Jr., Timothy Brydon Burnell, Juan Rodriques Ordonez, Ignacia Vic Fernandez, Gerardo Hidalgo-Llinas, Rudy Francois Alain J. Peemans, Edward Venama
  • Patent number: 6316578
    Abstract: This invention relates to a method for the preparation of polycarbonate by the melt process comprising reacting a diphenol and a diarylcarbonate in the presence of a catalyst system comprising a catalytically effective amount of an alkali and/or alkali earth metal salt of a non volatile acid and a base.
    Type: Grant
    Filed: February 4, 2000
    Date of Patent: November 13, 2001
    Assignee: General Electric Company
    Inventors: Patrick Joseph McCloskey, Timothy Brydon Burnell, Paul Michael Smigelski, Jr.
  • Patent number: 6300460
    Abstract: This invention relates to mixed dialkali metal salts of sulfuric acid containing at least one cesium equivalent useful in catalyst systems in melt polymerizations. The catalysts provide product with low branching side reaction products and good properties.
    Type: Grant
    Filed: July 6, 2000
    Date of Patent: October 9, 2001
    Assignee: General Electric Company
    Inventors: Patrick Joseph McCloskey, Timothy Brydon Burnell, Paul Michael Smigelski, Jr., Alberto Nisoli
  • Patent number: 6252013
    Abstract: A melt condensation polymerization process for preparing siloxane copolycarbonates is provided. The process includes reacting an aromatic dihydroxy compound, carbonic acid diester, hydroxyaryl terminated polydiorganosiloxane and catalyst with a salt.
    Type: Grant
    Filed: January 18, 2000
    Date of Patent: June 26, 2001
    Assignee: General Electric Company
    Inventors: Timothy Edward Banach, Gary Charles Davis, Paul Michael Smigelski, Jr., Patrick Joseph McCloskey
  • Patent number: 6252035
    Abstract: The present invention relates to a method for the preparation of polycarbonate comprising preparing a polycarbonate by a melt process by reacting a diphenol and a diaryl carbonate in the presence of a catalytically effective amount of one or more alkali and or alkali earth metal salts of chelating agents. Suitable chelating agents include nitrilotriacetate and EDTA.
    Type: Grant
    Filed: November 29, 1999
    Date of Patent: June 26, 2001
    Assignee: General Electric Company
    Inventors: Patrick Joseph McCloskey, Timothy Brydon Burnell, Paul Michael Smigelski, Jr.
  • Patent number: 6228973
    Abstract: A method of preparing polycarbonate by the melt process comprising the steps of: a) melting a dihydric phenol and a diester of carbonic acid for a time and at a temperature sufficient to form a melt; and thereafter introducing a catalyst composition comprising a tetraorganophosphonium salt or a derivative thereof and 1) an alkali and/or alkali earth metal compound or derivative thereof or 2) a less active alkali and/or alkali earth metal derivative thereof into the melt; and b) oligomerizing the product from step a) to a number average molecular weight of from about 3000 to about 7500; and c) polymerizing the product from step b) to a number average molecular weight of from about 16,000 to about 35,000.
    Type: Grant
    Filed: June 2, 2000
    Date of Patent: May 8, 2001
    Assignee: General Electric Company
    Inventors: Patrick Joseph McCloskey, Timothy Brydon Burnell, Paul Michael Smigelski, Jr., Johan Pieter Anna Heuts, Hendricus Franciscus Zirkzee
  • Patent number: 6184335
    Abstract: This invention relates to salts of aryl sulfonic acids useful in catalyst systems in melt polymerizations. Suitable alkali metal salts of aryl sulfonic acids include alkali metal salts of p-toluenesulfonic acid. The invention further relates to polycarbonates prepared using the catalyst systems of the present invention, and articles made from these polycarbonates.
    Type: Grant
    Filed: April 10, 2000
    Date of Patent: February 6, 2001
    Assignee: General Electric Company
    Inventors: Patrick Joseph McCloskey, Paul Michael Smigelski, Jr., Timothy Brydon Burnell
  • Patent number: 6184334
    Abstract: The present invention relates to a method for the preparation of polycarbonate comprising preparing a polycarbonate by a melt process by reacting a diphenol and a diaryl carbonate in the presence of a catalytically effective amount of one or more alkali metal salts of oxoacids of sulfur.
    Type: Grant
    Filed: October 4, 1999
    Date of Patent: February 6, 2001
    Assignee: General Electric Company
    Inventors: Patrick Joseph McCloskey, Timothy Brydon Burnell, Paul Michael Smigelski, Jr.