Patents by Inventor Paul Michael Smigelski
Paul Michael Smigelski 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: 20080004418Abstract: Polycarbonates incorporating terminal carbonate groups derived from ester-substituted activated carbonates in a transesterification process have unfavorable properties with respect to color, hydrolytic stability and thermal stability, particularly when the polycarbonate containing such end groups is molded. The number of activated carbonate end groups formed during the melt transesterification formation of polycarbonate can be reduced by reacting a dihydroxy compound with an activated diaryl carbonate in the presence of an esterification catalyst to produce a polycarbonate, in the presence of a monohydroxy chainstopper such as para-cumyl phenol in an amount that results in 35 to 65 mol % of the end groups being derived from the monohydroxy chainstopper. Suitably, the reactants are provided such that the molar ratio of activated diaryl carbonate to the total of dihydroxy compound plus ½ the chainstopping reagent that is less than 1.Type: ApplicationFiled: June 30, 2006Publication date: January 3, 2008Applicant: General Electric CompanyInventors: Bernd Jansen, Jan Henk Kamps, Edward Kung, Patrick Joseph McCloskey, Paul Michael Smigelski
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Publication number: 20080004407Abstract: A method for preparing a molded article includes the steps of (a) obtaining a polycarbonate resin and (b) molding the polycarbonate resin. The polycarbonate resin is made by a transesterification reaction using an activated diaryl carbonate such that the polycarbonate is susceptible to the formation of internal ester linkages (IEL). The method occurs with the proviso that the polycarbonate resin, the molding conditions or both are selected to control the amount of IEL formed during the molding process to a level of less than 0.4 mol %.Type: ApplicationFiled: March 20, 2007Publication date: January 3, 2008Applicant: GENERAL ELECTRIC COMPANYInventors: Sjef Berndsen, Hans-Peter Brack, Bernd Jansen, Jan Henk Kamps, Edward Kung, Daniel Lowery, Patrick Joseph McCloskey, Paul Michael Smigelski, Dennis Willemse
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Publication number: 20080004417Abstract: Polycarbonates incorporating terminal carbonate groups derived from ester-substituted activated carbonates, for example terminal methyl salicyl carbonate (TMSC) derived from the use of BMSC as the activated carbonate in a transesterification process, have unfavorable properties with respect to color, hydrolytic stability and thermal stability, particularly when the polycarbonate containing such end groups is molded. The number of activated carbonate end groups formed during the melt transesterification formation of polycarbonate can be reduced, however, without sacrificing the benefits of using an activated diaryl carbonate, and without requiring a separate reaction or additional additives by reacting a dihydroxy compound with an activated diaryl carbonate in the presence of an esterification catalyst to produce a polycarbonate, wherein the molar ratio of activated diaryl carbonate to dihydroxy compound is less than 1 when expressed to at least three decimal places, for example 0.996 or less.Type: ApplicationFiled: June 30, 2006Publication date: January 3, 2008Applicant: General Electric CompanyInventors: Bernd Jansen, Jan Henk Kamps, Edward Kung, Patrick Joseph McCloskey, Paul Michael Smigelski
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Patent number: 7294657Abstract: A composition comprising a phenylthioethylacrylate, a multifunctional (meth)acrylate, a curing agent, wherein the phenylthioethylacrylate comprises less than about 400 parts per million tin and less than about 2 percent by weight of the corresponding phenylthioethanol. The composition may further comprise at least one unsaturated acid.Type: GrantFiled: March 7, 2005Date of Patent: November 13, 2007Assignee: General Electric CompanyInventors: Daniel Robert Olson, Dennis Joseph Coyle, Christian Andrew Huntley, Bret Ja Chisholm, Paul Michael Smigelski, Jr., Alvin Un-Teh Chen
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Patent number: 7271283Abstract: Disclosed herein are high refractive index monomers that are curable by ultraviolet light. These monomers may be a component of curable compositions useful in the preparation of optical articles. Also disclosed is a method of synthesizing the monomers.Type: GrantFiled: July 21, 2004Date of Patent: September 18, 2007Assignee: General Electric CompanyInventors: Bret Ja Chisholm, Paul Michael Smigelski, Jr., James Edward Pickett
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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: 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: 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: 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: 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: 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: 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: 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: 6500914Abstract: 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: GrantFiled: October 10, 2001Date of Patent: December 31, 2002Assignee: General Electric CompanyInventors: Hans Peter Brack, James Anthony Cella, Dennis Karlik, Paul Michael Smigelski, Jr.
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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