Patents by Inventor Patrick Joseph McCloskey
Patrick Joseph McCloskey 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).
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Patent number: 7132498Abstract: The present invention relates to a method of preparing polycarbonate comprising the steps of: (i) introducing to an extruder through a feed port a plurality of reaction components comprising a polycarbonate oligomer, an activated carbonate residue, and a transesterification catalyst, wherein the extruder comprises the feed port, a first back vent port, and a polycarbonate exit port, wherein the feed port is located between the first back vent port and the polycarbonate exit port, and wherein the resistance to flow of the reaction components from the feed port to the first back vent port is less than or equal to the resistance to flow of the reaction components from the feed port to the polycarbonate exit port; and (ii) extruding the reaction components at one or more temperatures in a range between 100° C. and 400° C., wherein during the extrusion of the reaction components, activated carbonate residue is removed through the first back vent port, thereby preparing a polycarbonate.Type: GrantFiled: September 27, 2004Date of Patent: November 7, 2006Assignee: General Electric CompanyInventors: Patrick Joseph McCloskey, Norberto Silvi, Alberto Nisoli, Mark Giammattei
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Patent number: 7115700Abstract: 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: GrantFiled: May 19, 2005Date of Patent: October 3, 2006Assignee: General Electric CompanyInventors: James Anthony Cella, Jan Henk Kamps, Jan Pleun Lens, Kathryn Lynn Longley, Patrick Joseph McCloskey, Narayan Ramesh, Warren William Reilly, Paul Michael Smigelski, Jr., Marc Brian Wisnudel
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Patent number: 7041775Abstract: The present invention provides a method of making polycarbonate oligomers, polycarbonate, molded articles formed from polycarbonate, and an apparatus for making polycarbonate. An oligomer mixture is first prepared by the steps of providing an equilibration system comprising a vessel, a reaction mixture contained within the vessel, and means for mixing the reaction mixture contained within the vessel wherein the reaction mixture comprises a melted activated diaryl carbonate composition, and a catalyst present in sufficient amount to initiate an oligomerization reaction between a dihydroxy composition and the activated diaryl carbonate to form polycarbonate oligomers.Type: GrantFiled: April 21, 2004Date of Patent: May 9, 2006Assignee: General Electric CompanyInventors: Maria Tomas Martinez, Alberto Nisoli, Alfredo Lopez Carretero, Ganesh Kailasam, David Domingo, Patrick Joseph McCloskey
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Patent number: 6960641Abstract: A method of preparing block copolymers by solid state polymerization is described. A mixture of a partially crystalline polycarbonate having activated terminal aryloxy groups, for example terminal methyl salicyl groups, when heated together with an oligomeric polyester having reactive terminal hydroxy groups under solid state polymerization conditions affords block copolymers. The activated terminal aryloxy groups play a key role in preserving the block lengths of the starting materials. A control sample in which the partially crystalline polycarbonate lacks activated terminal aryloxy groups, for example polycarbonates substituted by phenol, affords a much lower molecular weight, more highly randomized copolymer product. The product block copolymers are useful as “weatherable” plastic materials.Type: GrantFiled: December 22, 2003Date of Patent: November 1, 2005Assignee: General Electric CompanyInventors: Gregory Allen O'Neil, James Day, Daniel Joseph Brunelle, Joseph Anthony Suriano, Patrick Joseph McCloskey, Paul Michael Smigelski, Jr.
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Patent number: 6900283Abstract: Stable, homogeneous melt solutions are prepared at temperatures of 200° C. or less from solid mixtures comprising at least one diaryl carbonate, at least one high melting dihydroxy aromatic compound (mp>200° C.), a transesterification catalyst, and optionally a lower melting dihydroxy aromatic compound. Thus, a stable, homogeneous melt solution is obtained from a solid mixture comprising 4,4?-biphenol (mp 282-284° C.) at a temperature of about 200° C. using either diphenyl carbonate or bis(methyl salicyl) carbonate as the diaryl carbonate component. It is shown that formation of the stable, homogeneous melt solutions requires the presence of the transesterification catalyst when substantial amounts of the high melting dihydroxy aromatic compound are present in the initial solid mixture. Solid mixtures comprising a variety of high melting bisphenols; 4,4?-biphenol; 3,3,3,3?-tetramethylspirobiindanbisphenol, and 4,4?-sulfonyidiphenol are converted to stable, homogeneous melt solutions at 200° C.Type: GrantFiled: November 4, 2002Date of Patent: May 31, 2005Assignee: General Electric CompanyInventors: Narayan Ramesh, Patrick Joseph McCloskey, Kathryn Lynn Longley
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Patent number: 6891015Abstract: High yields of ester-substituted diary carbonates such as bis-methyl salicyl carbonate were obtained by the condensation of ester-substituted phenols with phosgene in the presence of a phase transfer catalyst (PTC) and optionally a tertiary amine catalyst in a solvent free reaction system comprising an aqueous phase held at a pH of 8.3 or higher. The optimized conditions of the present invention use an excess of ester-substituted phenol relative to phosgene and high conversion of phosgene to ester-substituted diaryl carbonate is observed. The product ester-substituted diaryl carbonate may be conveniently isolated as a solid by filtration or as a liquid in which the excess ester-substituted phenols serves as solvent. The method represents an attractive route for the manufacture of bis methyl salicyl carbonate and ester-substituted diaryl carbonates generally. The ester-substituted diaryl carbonates are useful for the preparation and modification of polycarbonates.Type: GrantFiled: August 12, 2002Date of Patent: May 10, 2005Assignee: General Electric CompanyInventors: Timothy Brydon Burnell, Patrick Joseph McCloskey, Ganesh Kailasam, James Anthony Cella
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Patent number: 6870025Abstract: 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: GrantFiled: December 23, 2002Date of Patent: March 22, 2005Assignee: General Electric CompanyInventors: 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
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Patent number: 6809817Abstract: The present invention relates to methods and devices for in-situ measurement of reaction components of interest during manufacturing of polycarbonate by melt polymerization. The present invention describes irradiating a molten polymer sample with UV/visible light, and generating an absorbance profile correlated to Fries products as well as uncapped phenolic groups in the sample. The methods and apparatus of the invention are suitable for monitoring of Fries products in reactions ranging in size from small scale combinatorial formats to production scale reactors. Also included in methods of the invention are univariate and multivariate analysis for prediction of linear Fries, branched Fries and uncapped phenolic end-groups in unknowns.Type: GrantFiled: August 24, 2001Date of Patent: October 26, 2004Assignee: General Electric CompanyInventors: Radislav Alexandrovich Potyrailo, Patrick Joseph McCloskey, James Day
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Patent number: 6797802Abstract: The present invention provides a method of preparing polycarbonate, said method comprising (A) oligomerising in the presence of a catalyst at least one dihydroxyaromatic compound at a temperature in a range between about 220-280° C. and a pressure in a range between 180 mbar and 20 mbar, said catalyst comprising a tetraarylphosphonium compound and optionally a co-catalyst, to provide an oligomeric polycarbonate having a number average molecular weight, Mn, in a range between about 1000 and about 6000 daltons; and (B) in a second step heating the oligomeric polycarbonate formed in step (A) at a temperature range between about 280 and about 310° C. and a pressure in a range between about 15 mbar and about 0.1 mbar, to provide a polycarbonate having a weight average molecular weight, in a range between about 15,000 and about 50,000 daltons, said product polycarbonate comprising less than 1000 parts per million Fries product.Type: GrantFiled: October 7, 2002Date of Patent: September 28, 2004Assignee: General Electric CompanyInventors: Patrick Joseph McCloskey, Warren William Reilly
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Patent number: 6790929Abstract: 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: GrantFiled: March 17, 2003Date of Patent: September 14, 2004Assignee: General Electric CompanyInventors: Norberto Silvi, Mark Howard Giammattei, Patrick Joseph McCloskey, Alberto Nisoli, James Day, Narayan Ramesh, Paul Michael Smigelski, Jr., Paul Russell Wilson
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Publication number: 20040138383Abstract: A method of preparing block copolymers by solid state polymerization is described. A mixture of a partially crystalline polycarbonate having activated terminal aryloxy groups, for example terminal methyl salicyl groups, when heated together with an oligomeric polyester having reactive terminal hydroxy groups under solid state polymerization conditions affords block copolymers. The activated terminal aryloxy groups play a key role in preserving the block lengths of the starting materials. A control sample in which the partially crystalline polycarbonate lacks activated terminal aryloxy groups, for example polycarbonates substituted by phenol, affords a much lower molecular weight, more highly randomized copolymer product. The product block copolymers are useful as “weatherable” plastic materials.Type: ApplicationFiled: December 22, 2003Publication date: July 15, 2004Inventors: Gregory Allen O'Neil, James Day, Daniel Joseph Brunelle, Joseph Anthony Suriano, Patrick Joseph McCloskey, Paul Michael Smigelski
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Publication number: 20040087756Abstract: Stable, homogeneous melt solutions are prepared at temperatures of 200° C. or less from solid mixtures comprising at least one diaryl carbonate, at least one high melting dihydroxy aromatic compound (mp>200° C.), a transesterification catalyst, and optionally a lower melting dihydroxy aromatic compound. Thus, a stable, homogeneous melt solution is obtained from a solid mixture comprising 4,4′-biphenol (mp 282-284° C.) at a temperature of about 200° C. using either diphenyl carbonate or bis(methyl salicyl) carbonate as the diaryl carbonate component. It is shown that formation of the stable, homogeneous melt solutions requires the presence of the transesterification catalyst when substantial amounts of the high melting dihydroxy aromatic compound are present in the initial solid mixture.Type: ApplicationFiled: November 4, 2002Publication date: May 6, 2004Applicant: General Electric CompanyInventors: Narayan Ramesh, Patrick Joseph McCloskey, Kathryn Lynn Longley
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Patent number: 6723823Abstract: Mixed alkali metal salts of phosphoric acid in combination with a co-catalyst such as tetramethylammonium hydroxide (TMAH) are excellent transesterification catalysts for use in the preparation of polycarbonate from bisphenol A and diphenyl carbonate. The mixed alkali metal phosphate salts were shown by kinetic measurements made on a model system composed of p-tert-octylphenol and bis(p-cumylphenyl) carbonate to be inherently more potent catalysts than salts of phosphoric acid comprising a single alkali metal ion. In addition to providing higher rates of polymerization, the new catalysts were shown to provide polycarbonates containing reduced levels of Fries rearrangement product relative to polymerization reactions catalyzed by conventional catalyst systems such as sodium hydroxide together with TMAH co-catalyst.Type: GrantFiled: June 12, 2002Date of Patent: April 20, 2004Assignee: General Electric CompanyInventors: Patrick Joseph McCloskey, Warren William Reilly, Brian James Grimmond
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Publication number: 20040068087Abstract: The present invention provides a method of preparing polycarbonate, said method comprising (A) oligomerising in the presence of a catalyst at least one dihydroxyaromatic compound at a temperature in a range between about 220-280° C. and a pressure in a range between 180 mbar and 20 mbar, said catalyst comprising a tetraarylphosphonium compound and optionally a co-catalyst, to provide an oligomeric polycarbonate having a number average molecular weight, Mn, in a range between about 1000 and about 6000 daltons; and (B) in a second step heating the oligomeric polycarbonate formed in step (A) at a temperature range between about 280 and about 310° C. and a pressure in a range between about 15 mbar and about 0.1 mbar, to provide a polycarbonate having a weight average molecular weight, in a range between about 15,000 and about 50,000 daltons, said product polycarbonate comprising less than 1000 parts per million Fries product.Type: ApplicationFiled: October 7, 2002Publication date: April 8, 2004Applicant: General Electric CompanyInventors: Patrick Joseph McCloskey, Warren William Reilly
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Patent number: 6683689Abstract: The invention comprises UV/visible spectroscopic analysis of polycarbonate composition. The method comprises determination of the concentration of Fries products, as either total Fries products or as separate determinations of linear and branched components. The method also allows for simultaneous determination of uncapped phenolic end-groups. Determinations may be performed at a single wavelength or over the entire absorption band. The method is suitable for measuring of Fries products in samples ranging in size from small scale combinatorial formats to production scale reactors. The method is independent of reaction variables such as polymer molecular weight, reactor type, and reaction temperature.Type: GrantFiled: October 2, 2001Date of Patent: January 27, 2004Assignee: General Electric CompanyInventors: Radislav Alexandrovich Potyrailo, Patrick Joseph McCloskey
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Publication number: 20030236384Abstract: 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: ApplicationFiled: March 17, 2003Publication date: December 25, 2003Applicant: General Electric CompanyInventors: Norberto Silvi, Mark Howard Giammattei, Patrick Joseph McCloskey, Alberto Nisoli, James Day, Narayan Ramesh, Paul Michael Smigelski, Paul Russell Wilson
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Publication number: 20030236383Abstract: Mixed alkali metal salts of phosphoric acid in combination with a co-catalyst such as tetramethylammonium hydroxide (TMAH) are excellent transesterification catalysts for use in the preparation of polycarbonate from bisphenol A and diphenyl carbonate. The mixed alkali metal phosphate salts were shown by kinetic measurements made on a model system composed of p-tert-octylphenol and bis(p-cumylphenyl) carbonate to be inherently more potent catalysts than salts of phosphoric acid comprising a single alkali metal ion. In addition to providing higher rates of polymerization, the new catalysts were shown to provide polycarbonates containing reduced levels of Fries rearrangement product relative to polymerization reactions catalyzed by conventional catalyst systems such as sodium hydroxide together with TMAH co-catalyst.Type: ApplicationFiled: June 12, 2002Publication date: December 25, 2003Applicant: General Electric CompanyInventors: Patrick Joseph McCloskey, Warren William Reilly, Brian James Grimmond
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Publication number: 20030232957Abstract: 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: ApplicationFiled: June 12, 2002Publication date: December 18, 2003Applicant: General Electric CompanyInventors: Norberto Silvi, Patrick Joseph McCloskey, James Day, Mark Howard Giammattei
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Patent number: 6608678Abstract: The present invention provides a method for monitoring a reaction mixture using Raman spectroscopy. In a preferred embodiment, the invention provides a method for monitoring bulk and thin film melt polycarbonate polymerization reactions. In this method, the relative and absolute concentrations of the starting materials diphenylcarbonate (DPC) and bisphenol-A (BPA) are determined. Monitoring and maintenance of optimum stoichiometry in such a reaction is critical to ensuring desired polycarbonate product quality.Type: GrantFiled: October 19, 2000Date of Patent: August 19, 2003Assignee: General Electric CompanyInventors: Radislav Alexandrovich Potyrailo, Ronald Eugene Shaffer, Patrick Joseph McCloskey
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Patent number: RE38995Abstract: 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: GrantFiled: August 15, 2003Date of Patent: February 28, 2006Assignee: General Electric CompanyInventors: Patrick Joseph McCloskey, Timothy Brydon Burnell, Daniel Joseph Brunelle, Elliott West Shanklin, Paul Michael Smigelski, Jr., Ganesh Kailasam