Patents by Inventor Benny D. Freeman

Benny D. Freeman 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: 11613649
    Abstract: Polymer blends comprising an ortho-functionalized polyimide homo or copolymer and a polybenzimidazole homo or copolymer, wherein the ortho-functionalized polyimide thermally rearranges to a polymer comprising a phenylene heterocyclic group, such as, polybenzoxazole, polybenzothiazole, polybenzimidazole and/or other heterocyclic structure upon heating. Also disclosed are method of forming a polymer blend comprising dissolving an ortho-functionalized polyimide homo or copolymer and a polybenzimidazole homo or copolymer in a solvent, and optional compatibilizer, to form a polymer solution; contacting a support with the polymer solution; and evaporating the solvent to provide a thin layer comprising the polymer blend on the support. Further, methods of heat treating these polymer blends to thermally rearrange the disclosed polyimides are disclosed, as are the polymer blends prepared thereby. Methods of using these polymer blends to separate gases are also disclosed.
    Type: Grant
    Filed: April 2, 2019
    Date of Patent: March 28, 2023
    Assignee: BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM
    Inventors: Benny D. Freeman, Donald R. Paul, Joshua D. Moon
  • Patent number: 11525034
    Abstract: Described herein are water desalination membranes and methods of desalinating water. Sulfonated poly(arylene ether) polymers are also disclosed, including those comprising one or more sulfonate groups at various points along the polymer chain. The polymers may be used as at least a portion of a water desalination membrane. The polymers described herein are useful for preventing transport of aqueous ionic species (e.g., Na+ and Cl?) across a membrane made from the polymers while allowing water to pass. Chlorine-stable polymers are described, as well as polymers exhibiting good performance for rejecting monovalent cations in the presence of polyvalent cations.
    Type: Grant
    Filed: July 31, 2020
    Date of Patent: December 13, 2022
    Assignees: Board of Regents, The University of Texas System, Virginia Tech Intellectual Properties, Inc.
    Inventors: Judy S. Riffle, Ozma R. Lane, Amin Daryaei, Shreya Roy-Choudhury, Benny D. Freeman, Eui Soung Jang, Gurtej S. Narang, John J. Lesko, Trevor Schumacher
  • Patent number: 11420916
    Abstract: The present disclosure pertains to methods and systems for separating olefins from a mixture that includes olefins and non-olefins. The methods include associating the mixture with a support that is embedded with an ionic liquid and a metal ion. The ionic liquid prevents the substantial reduction of the metal ion by reducing agents while the metal ion mediates the transport of the olefin through the support by selectively and reversibly coupling with the olefin. In some embodiments, the support may be in the form of supported ionic liquid porous membranes, and the ionic liquid may be held within the pores of the support by capillary forces. In some embodiments, the support may be in the form of a composite, and the ionic liquid may be dispersed throughout the composite. In some embodiments, the metal ion may be dissolved in the ionic liquid and dispersed throughout the support.
    Type: Grant
    Filed: June 10, 2019
    Date of Patent: August 23, 2022
    Assignee: Board of Regents, The University of Texas System
    Inventors: Joan F. Brennecke, Benny D. Freeman, Constanza Miguel Sanchez
  • Publication number: 20210246089
    Abstract: The present disclosure pertains to methods and systems for separating olefins from a mixture that includes olefins and non-olefins. The methods include associating the mixture with a support that is embedded with an ionic liquid and a metal ion. The ionic liquid prevents the substantial reduction of the metal ion by reducing agents while the metal ion mediates the transport of the olefin through the support by selectively and reversibly coupling with the olefin. In some embodiments, the support may be in the form of supported ionic liquid porous membranes, and the ionic liquid may be held within the pores of the support by capillary forces. In some embodiments, the support may be in the form of a composite, and the ionic liquid may be dispersed throughout the composite. In some embodiments, the metal ion may be dissolved in the ionic liquid and dispersed throughout the support.
    Type: Application
    Filed: June 10, 2019
    Publication date: August 12, 2021
    Inventors: Joan F. Brennecke, Benny D. Freeman, Constanza Miguel Sanchez
  • Publication number: 20210095122
    Abstract: Polymer blends comprising an ortho-functionalized polyimide homo or copolymer and a polybenzimidazole homo or copolymer, wherein the ortho-functionalized polyimide thermally rearranges to a polymer comprising a phenylene heterocyclic group, such as, polybenzoxazole, polybenzothiazole, polybenzimidazole and/or other heterocyclic structure upon heating. Also disclosed are method of forming a polymer blend comprising dissolving an ortho-functionalized polyimide homo or copolymer and a polybenzimidazole homo or copolymer in a solvent, and optional compatibilizer, to form a polymer solution; contacting a support with the polymer solution; and evaporating the solvent to provide a thin layer comprising the polymer blend on the support. Further, methods of heat treating these polymer blends to thermally rearrange the disclosed polyimides are disclosed, as are the polymer blends prepared thereby. Methods of using these polymer blends to separate gases are also disclosed.
    Type: Application
    Filed: April 2, 2019
    Publication date: April 1, 2021
    Inventors: Benny D. FREEMAN, Donald R. PAUL, Joshua D. MOON
  • Publication number: 20200362107
    Abstract: Described herein are water desalination membranes and methods of desalinating water. Sulfonated poly(arylene ether) polymers are also disclosed, including those comprising one or more sulfonate groups at various points along the polymer chain. The polymers may be used as at least a portion of a water desalination membrane. The polymers described herein are useful for preventing transport of aqueous ionic species (e.g., Na+ and Cl?) across a membrane made from the polymers while allowing water to pass. Chlorine-stable polymers are described, as well as polymers exhibiting good performance for rejecting monovalent cations in the presence of polyvalent cations.
    Type: Application
    Filed: July 31, 2020
    Publication date: November 19, 2020
    Applicants: Board of Regents, The University of Texas System, Virginia Tech Intellectual Properties, Inc.
    Inventors: Judy S. Riffle, Ozma R. Lane, Amin Daryaei, Shreya Roy-Choudhury, Benny D. Freeman, Eui Soung Jang, Gurtej S. Narang, John J. Lesko, Trevor Schumacher
  • Patent number: 10188992
    Abstract: Disclosed are polybenzimidazoles containing sulfonyl groups. The polymers can be synthesized in Eaton's reagent from 3,3?,4,4?-tetraaminodiphenylsulfone, which itself can be synthesized from 4,4?-dichlorodiphenylsulfone. Methods of synthesizing the polymers are disclosed. The disclosed polymers can be used for high temperature H2/CO2 separation membranes and other uses.
    Type: Grant
    Filed: September 19, 2016
    Date of Patent: January 29, 2019
    Assignees: Board of Regents, The University of Texas System, Virginia Tech Intellectual Properties, Inc.
    Inventors: James E. McGrath, Judy S. Riffle, Benny D. Freeman
  • Patent number: 9724900
    Abstract: A method of fabricating a gas separation membrane includes providing a coextruded multilayer film that includes a first polymer layer formed of a first polymer material and a second polymer layer formed of a second polymer material, the first polymer material having a first gas permeability. The coextruded multilayer film is axially oriented such that the second polymer layer has a second gas permeability that is greater than the first gas permeability.
    Type: Grant
    Filed: December 15, 2014
    Date of Patent: August 8, 2017
    Assignees: Case Western Reserve University, The University of Texas at Austin
    Inventors: Eric Baer, Shannon Armstrong, Benny D. Freeman, Donald R. Paul, Grant Offord
  • Publication number: 20170081477
    Abstract: Disclosed are polybenzimidazoles containing sulfonyl groups. The polymers can be synthesized in Eaton's reagent from 3,3?,4,4?-tetraaminodiphenylsulfone, which itself can be synthesized from 4,4?-dichlorodiphenylsulfone. Methods of synthesizing the polymers are disclosed. The disclosed polymers can be used for high temperature H2/CO2 separation membranes and other uses.
    Type: Application
    Filed: September 19, 2016
    Publication date: March 23, 2017
    Inventors: James E. McGrath, Judy S. Riffle, Benny D. Freeman
  • Publication number: 20150298436
    Abstract: A method of fabricating a gas separation membrane includes providing a coextruded multilayer film that includes a first polymer layer formed of a first polymer material and a second polymer layer formed of a second polymer material, the first polymer material having a first gas permeability. The coextruded multilayer film is axially oriented such that the second polymer layer has a second gas permeability that is greater than the first gas permeability.
    Type: Application
    Filed: December 15, 2014
    Publication date: October 22, 2015
    Inventors: Eric Baer, Shannon Armstrong, Benny D. Freeman, Donald R. Paul, Grant Offord
  • Patent number: 8911540
    Abstract: A method of fabricating a gas separation membrane includes providing a coextruded multilayer film that includes a first polymer layer formed of a first polymer material and a second polymer layer formed of a second polymer material, the first polymer material having a first gas permeability. The coextruded multilayer film is axially oriented such that the second polymer layer has a second gas permeability that is greater than the first gas permeability.
    Type: Grant
    Filed: May 1, 2013
    Date of Patent: December 16, 2014
    Assignee: Case Western Reserve University
    Inventors: Eric Baer, Shannon Armstrong, Benny D. Freeman, Donald R. Paul, Grant Offord
  • Publication number: 20130291729
    Abstract: A method of fabricating a gas separation membrane includes providing a coextruded multilayer film that includes a first polymer layer formed of a first polymer material and a second polymer layer formed of a second polymer material, the first polymer material having a first gas permeability. The coextruded multilayer film is axially oriented such that the second polymer layer has a second gas permeability that is greater than the first gas permeability.
    Type: Application
    Filed: May 1, 2013
    Publication date: November 7, 2013
    Applicant: Case Western Reserve University
    Inventors: Eric Baer, Shannon Armstrong, Benny D. Freeman, Donald R. Paul, Grant Offord
  • Publication number: 20120329958
    Abstract: The present invention includes a polymer formed by the thermal rearrangement of an ortho-functional polyimide synthesized via chemical imidization with permeation properties for gas separation membranes higher than those synthesized via thermal imidization and a method for forming that polymer having tailored transport properties and different chemical resistance. The present invention also includes a polymer formed by the thermal rearrangement of an ortho-functional polyimide in which a portion of the ortho-position functional group is lost during thermal rearrangement to yield a thermally rearranged polymer with higher permeability than would be seen without the ortho-position group. This ortho-position group can be the result of chemical imidization, or the result of a post-imidization modification reaction.
    Type: Application
    Filed: June 1, 2012
    Publication date: December 27, 2012
    Applicants: Virginia Tech Intellectual Properties, Inc., Board of Regents, The University of Texas System
    Inventors: Benny D. Freeman, David Sanders, Claudio P. Ribeiro, JR., Zachary Smith, James E. McGrath, Ruilan Guo
  • Publication number: 20120305484
    Abstract: Synthesis and use of a new class of polymeric materials with favorable separation characteristics for the dehydration of ethanol and other organic solvents is described herein. The thermally rearranged (TR) polybenzoxazole (PBO), polybenzimidazole (PBI) and polybenzothiazole (PBT) membranes of the present invention can be used for the dehydration of ethanol during processing to fuel grade biodiesel by either pervaporation or vapor permeation. The unique microstructure of the membranes provides excellent separation characteristics, and this, coupled with their inherent thermal and chemical stability, enables their usage in other separations, such as the dehydration of other organic solvents.
    Type: Application
    Filed: June 3, 2011
    Publication date: December 6, 2012
    Applicant: Board of Regents, The University of Texas System
    Inventors: Benny D. Freeman, Donald R. Paul, Katrina Czenkusch, Claudio P. Ribeiro, JR., Chaoyi Ba
  • Publication number: 20120111791
    Abstract: The present invention includes methods and compositions for liquid separation and water purification. The present invention includes a purification membrane having a polymer matrix purification membrane that has been treated with hydroquinone, catechol, and/or dopamine coated membrane with a high water flux.
    Type: Application
    Filed: November 4, 2010
    Publication date: May 10, 2012
    Applicant: Board of Regents, The University of Texas System
    Inventors: Benny D. Freeman, Daniel J. Miller, Bryan D. McCloskey, Christopher W. Bielawski, Daniel R. Dreyer
  • Patent number: 8163814
    Abstract: Azidoaryl-substituted cyclooctene monomers and synthesized and used in the preparation of various copolymers. Among these copolymers are those prepared from ring-opening metathesis polymerization of cyclooctene, polyethylene glycol-substituted cyclooctene, and azidoaryl-substituted cyclooctene. These copolymers are useful in the formation of crosslinked films that reduce fouling of water purification membranes.
    Type: Grant
    Filed: February 11, 2011
    Date of Patent: April 24, 2012
    Assignees: The University of Massachusetts, Board of Regents, The University of Texas System
    Inventors: Todd Shannon Emrick, Kurt Breitenkamp, Ravindra Revanur, Benny D. Freeman, Bryan McCloskey
  • Patent number: 8028842
    Abstract: The present invention provides a membrane, kit, and method of making a hydrophilic-hydrophobic random copolymer membrane. The hydrophilic-hydrophobic random copolymer membrane includes a hydrophilic-hydrophobic random copolymer. The hydrophilic-hydrophobic random copolymer includes one or more hydrophilic monomers having a sulfonated polyarylsulfone monomer and a second monomer and one or more hydrophobic monomers having a non-sulfonated third monomer and a fourth monomer. The sulfonated polyarylsulfone monomer introduces a sulfonate into the hydrophilic-hydrophobic random copolymer prior to polymerization.
    Type: Grant
    Filed: January 18, 2007
    Date of Patent: October 4, 2011
    Assignee: Virginia Tech Intellectual Properties, Inc.
    Inventors: James E. McGrath, Ho Bum Park, Benny D. Freeman
  • Patent number: 8017050
    Abstract: The present invention includes methods and compositions for liquid separation and water purification. The present invention includes a purification membrane having a polymer matrix purification membrane that has been treated with dopamine to form a polydopamine coated membrane with a high water flux and a high hydrophilicity.
    Type: Grant
    Filed: July 9, 2009
    Date of Patent: September 13, 2011
    Assignee: Board of Regents The University of Texas System
    Inventors: Benny D. Freeman, Ho Bum Park, Bryan D. McCloskey
  • Publication number: 20110139709
    Abstract: Azidoaryl-substituted cyclooctene monomers and synthesized and used in the preparation of various copolymers. Among these copolymers are those prepared from ring-opening metathesis polymerization of cyclooctene, polyethylene glycol-substituted cyclooctene, and azidoaryl-substituted cyclooctene. These copolymers are useful in the formation of crosslinked films that reduce fouling of water purification membranes.
    Type: Application
    Filed: February 11, 2011
    Publication date: June 16, 2011
    Inventors: Todd Shannon Emrick, Kurt Breitenkamp, Ravindra Revanur, Benny D. Freeman, Bryan McCloskey
  • Publication number: 20100059433
    Abstract: The present invention describes methods and compositions for the reduction, prevention and elimination of biofilm formation on a surface. The present invention provides a method of depositing a coating material to reduce or prevent biofilm formation on a surface by adding a dopamine coating material to a liquid solvent to form a solution mixture, adjusting a pH of the solution mixture to 8, 9, or 10 and dissolving the dopamine coating material in the liquid solvent. The solution mixture is then placed into contact with one or more surfaces to form a dopamine coating on the surface to reduce biofilm formation.
    Type: Application
    Filed: July 9, 2009
    Publication date: March 11, 2010
    Applicant: Board of Regents, The University of Texas System
    Inventors: Benny D. Freeman, Ho Bum Park, Bryan D. McCloskey, Daniel J. Miller