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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Publication number: 20030149223Abstract: 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: ApplicationFiled: December 23, 2002Publication date: August 7, 2003Applicant: 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, Marc Brian Wisnudel
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Patent number: 6600004Abstract: A method of preparing polyestercarbonates is presented in which a mixture of at least one activated diaryl carbonate is reacted under melt polymerization conditions with at least one aromatic dihydroxy compound together with at least one dicarboxylic acid. Polyestercarbonates possessing up to about percent 10 mole dicarboxylic acid residues based on the total amount of structural units derived from aromatic dihydroxy compounds are obtained. The method provides both for high levels of incorporation of the dicarboxylic acid into the polyestercarbonate backbone and a high level of polymer endcapping.Type: GrantFiled: April 10, 2002Date of Patent: July 29, 2003Assignee: General Electric CompanyInventors: Patrick Joseph McCloskey, Paul Michael Smigelski
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Publication number: 20030139529Abstract: 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: November 2, 2001Publication date: July 24, 2003Applicant: General Electric CompanyInventors: Gregory Allen O'Neil, James Day, Daniel Joseph Brunelle, Joseph Anthony Suriano, Patrick Joseph McCloskey, Paul Michael Smigelski
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Patent number: 6576801Abstract: 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: GrantFiled: February 25, 2002Date of Patent: June 10, 2003Assignee: General Electric CompanyInventors: Paul Michael Smigelski, Jr., Timothy Brydon Burnell, Patrick Joseph McCloskey
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Patent number: 6576911Abstract: In an embodiment, the present invention is directed a method and an apparatus comprising irradiating a polymer sample with at least one wavelength of substantially monochromatic light and monitoring radiation emitted by the polymer sample which is correlated to sample hydrolysis and a change in polymer molecular weight.Type: GrantFiled: October 19, 2000Date of Patent: June 10, 2003Assignee: General Electric CompanyInventors: Radislav Alexandrovich Potyrailo, Patrick Joseph McCloskey, Timothy Brydon Burnell
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Patent number: 6569985Abstract: Polycarbonates having a high level of endcapping and containing a low level of Fries rearrangement product are prepared from dihydroxy aromatic compounds, such as bisphenol A, and diaryl carbonates such as diphenyl carbonate in a two stage process involving a tetraalkyl phosphonium carboxylate catalyzed oligomerization of the reactants in a first reaction stage followed by the addition of an alkali metal hydroxide co-catalyst in the second stage of the polymerization reaction. The late addition of the co-catalyst provides improved polymerization reaction rates as judged by higher polycarbonate molecular weights. The amount of alkali metal hydroxide co-catalyst is small thus avoiding the formation of excessive amounts of Fries product. The method has been used to provide Fries product levels between 200 and 800 parts per million in polycarbonates having Mn values between 7,500 and 8,500 Daltons.Type: GrantFiled: August 8, 2001Date of Patent: May 27, 2003Assignee: General Electric CompanyInventors: Patrick Joseph McCloskey, Alberto Nisoli, Warren William Reilly
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Patent number: 6548623Abstract: 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: GrantFiled: July 24, 2001Date of Patent: April 15, 2003Assignee: General Electric CompanyInventors: Daniel Joseph Brunelle, Patrick Joseph McCloskey, Paul Michael Smigelski, Jr., Timothy Brydon Burnell, Ganesh Kailasam
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Publication number: 20030063282Abstract: 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: ApplicationFiled: October 2, 2001Publication date: April 3, 2003Inventors: Radislav Alexandrovich Potyrailo, Patrick Joseph McCloskey
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Publication number: 20030065129Abstract: Polycarbonates having a high level of endcapping and containing a low level of Fries rearrangement product are prepared from dihydroxy aromatic compounds, such as bisphenol A, and diaryl carbonates such as diphenyl carbonate in a two stage process involving a tetraalkyl phosphonium carboxylate catalyzed oligomerization of the reactants in a first reaction stage followed by the addition of an alkali metal hydroxide co-catalyst in the second stage of the polymerization reaction. The late addition of the co-catalyst provides improved polymerization reaction rates as judged by higher polycarbonate molecular weights. The amount of alkali metal hydroxide co-catalyst is small thus avoiding the formation of excessive amounts of Fries product. The method has been used to provide Fries product levels between 200 and 800 parts per million in polycarbonates having Mn values between 7,500 and 8,500 Daltons.Type: ApplicationFiled: August 8, 2001Publication date: April 3, 2003Applicant: General Electric CompanyInventors: Patrick Joseph McCloskey, Alberto Nisoli, WARREN WILLIAM REILLY
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Publication number: 20030060649Abstract: 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: ApplicationFiled: August 12, 2002Publication date: March 27, 2003Applicant: General Electric CompanyInventors: Timothy Brydon Burnell, Patrick Joseph McCloskey, Ganesh Kailasam, James Anthony Cella
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Publication number: 20030053050Abstract: 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: ApplicationFiled: August 24, 2001Publication date: March 20, 2003Inventors: Radislav Alexandrovich Potyrailo, Patrick Joseph McCloskey, James Day
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Publication number: 20030050427Abstract: 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: ApplicationFiled: July 24, 2001Publication date: March 13, 2003Applicant: General Electric CompanyInventors: Daniel Joseph Brunelle, Patrick Joseph McCloskey, Paul Michael Smigelski, Timothy Brydon Burnell, Ganesh Kailasam
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Patent number: 6518391Abstract: 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: GrantFiled: July 24, 2001Date of Patent: February 11, 2003Assignee: General Electric CompanyInventors: Patrick Joseph McCloskey, James Day, Paul Michael Smigelski, Jr., Timothy Brydon Burnell
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Patent number: 6506871Abstract: Extrusion of a mixture of an ester-substituted diaryl carbonate, such as bis(methyl salicyl) carbonate, a dihydroxy aromatic compound such as bisphenol A and a transesterification catalyst such as tetrabutylphosphonium acetate (TBPA) affords polycarbonate having a weight average molecular weight of greater than 20,000 daltons. The extruder is equipped with one or more vacuum vents to remove by-product ester-substituted phenol. Similarly, a precursor polycarbonate having ester-substituted phenoxy endgroups, for example methyl salicyl endgroups, when subjected to extrusion affords a polycarbonate having a significantly increased molecular weight relative to the precursor polycarbonate. The reaction to form a higher molecular weight polycarbonate may be catalyzed by residual transesterification catalyst present in the precursor polycarbonate, or by a combination of any residual catalyst and an additional catalyst such as TBPA introduced in the extrusion step.Type: GrantFiled: June 12, 2002Date of Patent: January 14, 2003Assignee: General Electric CompanyInventors: Norberto Silvi, Patrick Joseph McCloskey, James Day, Mark Howard Giammattei
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Patent number: 6492485Abstract: The application relates to methods for producing a polycarbonate resin having a narrowed molecular weight distribution, specifically, the application relates to the use of a redistribution catalyst and a feedback loop control mechanism to prepare narrow molecular weight distribution resin.Type: GrantFiled: April 11, 2000Date of Patent: December 10, 2002Assignee: General Electric CompanyInventors: Eric Thomas Gohr, Chad David Mistele, Michael F. Shannon, Vijaykumar Hanagandi, Devesh Mathur, Patrick Joseph McCloskey
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Patent number: 6469192Abstract: 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.Type: GrantFiled: July 24, 2001Date of Patent: October 22, 2002Assignee: General Electric CompanyInventors: Timothy Brydon Burnell, Patrick Joseph McCloskey, Ganesh Kailasam, James Anthony Cella
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Publication number: 20020143134Abstract: 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: ApplicationFiled: February 25, 2002Publication date: October 3, 2002Inventors: Paul Michael Smigelski, Timothy Brydon Burnell, Patrick Joseph McCloskey
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Patent number: 6420588Abstract: 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: July 24, 2001Date of Patent: July 16, 2002Assignee: General Electric CompanyInventors: Patrick Joseph McCloskey, Timothy Brydon Burnell, Daniel Joseph Brunelle, Elliott West Shanklin, Paul Michael Smigelski, Jr., Ganesh Kailasam
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Patent number: 6420512Abstract: Extrusion of a mixture of an ester-substituted diaryl carbonate, such as bis-methyl salicyl carbonate, a dihydroxy aromatic compound such as bisphenol A and a transesterification catalyst such as tetrabutyl phosphonium acetate (TBPA) affords polycarbonate having a weight average molecular weight of greater than 20,000 Daltons. The extruder is equipped with one or more vacuum vents to remove by-product ester-substituted phenol. Similarly, a precursor polycarbonate having ester-substituted phenoxy endgroups, for example methyl salicyl endgroups, when subjected to extrusion affords a polycarbonate having a significantly increased molecular weight relative to the precursor polycarbonate. The reaction to form a higher molecular weight polycarbonate may be catalyzed by residual transesterification catalyst present in the precursor polycarbonate, or by a combination of any residual catalyst and an additional catalyst such as TBPA introduced in the extrusion step.Type: GrantFiled: July 24, 2001Date of Patent: July 16, 2002Assignee: General Electric CompanyInventors: Patrick Joseph McCloskey, James Day, Paul Michael Smigelski, John Lester Maxam, John Aibangbee Osaheni
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Patent number: 6414106Abstract: 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: GrantFiled: March 2, 2001Date of Patent: July 2, 2002Assignee: General Electric CompanyInventors: Paul Michael Smigelski, Jr., Timothy Brydon Burnell, Patrick Joseph McCloskey