Porous compositions and related methods

Swager, Timothy M.; He, Yuan; Smith, Zachary; Lin, Sharon; Benedetti, Francesco Maria

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Title: Porous compositions and related methods

Abstract

Porous compositions such as flexible polymers with side chain porosity are generally provided. In some embodiments, the composition comprises a flexible polymer backbone and a plurality of rigid side chains. In some embodiments, the rigid side chains form pores. In some embodiments, the rigid side chains may comprise two or more [2.2.2] bicyclic cores (e.g., formed by a ring opening metathesis polymerization. The compounds and methods described herein may be useful in various applications including, for example, gas separation.

Inventors:: Swager, Timothy M.; He, Yuan; Smith, Zachary; Lin, Sharon; Benedetti, Francesco Maria

Issue Date:: 2022-10-18

Research Org.:: Massachusetts Inst. of Technology (MIT), Cambridge, MA (United States)

Sponsoring Org.:: USDOE; National Science Foundation (NSF)

OSTI Identifier:: 1986708

Patent Number(s):: 11472915

Application Number:: 16/435,397

Assignee:: Massachusetts Institute of Technology (Cambridge, MA)

DOE Contract Number:: SC0019087; DMR-1410718

Resource Type:: Patent

Resource Relation:: Patent File Date: 06/07/2019

Country of Publication:: United States

Language:: English

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                    Swager, Timothy M., He, Yuan, Smith, Zachary, Lin, Sharon, and Benedetti, Francesco Maria. Porous compositions and related methods.  United States: N. p., 2022. 
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                    Swager, Timothy M., He, Yuan, Smith, Zachary, Lin, Sharon, & Benedetti, Francesco Maria. Porous compositions and related methods.  United States.

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                    Swager, Timothy M., He, Yuan, Smith, Zachary, Lin, Sharon, and Benedetti, Francesco Maria. Tue .  
        "Porous compositions and related methods".  United States.  https://www.osti.gov/servlets/purl/1986708.

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@article{osti_1986708,

  title        = {Porous compositions and related methods},

  author       = {Swager, Timothy M. and He, Yuan and Smith, Zachary and Lin, Sharon and Benedetti, Francesco Maria},

  abstractNote = {Porous compositions such as flexible polymers with side chain porosity are generally provided. In some embodiments, the composition comprises a flexible polymer backbone and a plurality of rigid side chains. In some embodiments, the rigid side chains form pores. In some embodiments, the rigid side chains may comprise two or more [2.2.2] bicyclic cores (e.g., formed by a ring opening metathesis polymerization. The compounds and methods described herein may be useful in various applications including, for example, gas separation.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {2022},

  month        = {10}

}

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Composite media for fluid stream processing, a method of forming the composite media, and a related method of processing a fluid stream

Patent Garn, Troy G; Law, Jack D; Greenhalgh, Mitchell R; ...

A composite media including at least one crystalline aluminosilicate material in polyacrylonitrile. A method of forming a composite media is also disclosed. The method comprises dissolving polyacrylonitrile in an organic solvent to form a matrix solution. At least one crystalline aluminosilicate material is combined with the matrix solution to form a composite media solution. The organic solvent present in the composite media solution is diluted. The composite media solution is solidified. In addition, a method of processing a fluid stream is disclosed. The method comprises providing a beads of a composite media comprising at least one crystalline aluminosilicate material dispersedmore » « less
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Compositions, systems and methods using selective porous materials for oxygen separation

Patent Nenoff, Tina M.; Sava Gallis, Dorina Florentina; Parkes, Marie Vernell; ...

MOFs are disclosed that can efficiently adsorb oxygen from a gas stream, such as air. Systems and methods are also disclosed that utilize MOFs to separate oxygen from a gas stream. The separated oxygen may be used in a commercial process such as a combustion process.
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Method of forming a dense, high temperature electronically conductive composite layer on a porous ceramic substrate

Patent Isenberg, Arnold O [Pittsburgh, PA]

An electrochemical device, containing a solid oxide electrolyte material and an electrically conductive composite layer, has the composite layer attached by: (A) applying a layer of LaCrO.sub.3, YCrO.sub.3 or LaMnO.sub.3 particles (32), on a portion of a porous ceramic substrate (30), (B) heating to sinter bond the particles to the substrate, (C) depositing a dense filler structure (34) between the doped particles (32), (D) shaving off the top of the particles, and (E) applying an electronically conductive layer over the particles (32) as a contact.
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Title: Porous compositions and related methods

Abstract

Citation Formats

Polymer of Intrinsic Microporosity Incorporating Thioamide Functionality: Preparation and Gas Transport Properties journal, August 2011

CO2-induced plasticization phenomena in glassy polymers journal, March 1999

Influence of methanol conditioning and physical aging on carbon spin-lattice relaxation times of poly(1-trimethylsilyl-1-propyne) journal, November 2004

Mixed-gas permeation of syngas components in poly(dimethylsiloxane) and poly(1-trimethylsilyl-1-propyne) at elevated temperatures journal, September 2001

Effect of Temperature on Physical Aging of Thin Glassy Polymer Films journal, November 2005

Synthesis and gas permeation properties of novel spirobisindane-based polyimides of intrinsic microporosity journal, January 2013

Filter materials including functionalized cellulose patent, September 2021

Mixed gas sorption in glassy polymeric membranes: I. CO2/CH4 and n-C4/CH4 mixtures sorption in poly(1-trimethylsilyl-1-propyne) (PTMSP) journal, January 2014

Porous Organic Polymers via Ring Opening Metathesis Polymerization journal, February 2018

Sub-Tg Cross-Linking of a Polyimide Membrane for Enhanced CO2 Plasticization Resistance for Natural Gas Separation journal, August 2011

Pure- and mixed-gas permeation of CO2 and CH4 in thermally rearranged polymers based on 3,3′-dihydroxy-4,4′-diamino-biphenyl (HAB) and 2,2′-bis-(3,4-dicarboxyphenyl) hexafluoropropane dianhydride (6FDA) journal, February 2015

Carbon dioxide plasticization of thin glassy polymer films journal, November 2011

Emissive polymers and devices incorporating these polymers patent, April 2007

Gas sorption and permeation in PIM-1 journal, April 2013

Avogadro: an advanced semantic chemical editor, visualization, and analysis platform journal, August 2012

Polymers of intrinsic microporosity (PIMs): robust, solution-processable, organic nanoporous materials journal, January 2004

An Efficient Polymer Molecular Sieve for Membrane Gas Separations journal, January 2013

Polymers with high internal free volume patent, February 2009

Pure- and mixed-gas permeation properties of highly selective and plasticization resistant hydroxyl-diamine-based 6FDA polyimides for CO2/CH4 separation journal, May 2016

Effect of physical aging on the gas transport and sorption in PIM-1 membranes journal, March 2017

Physical aging, CO 2 sorption and plasticization in thin films of polymer with intrinsic microporosity (PIM-1) journal, September 2017

Polymer ultrapermeability from the inefficient packing of 2D chains journal, July 2017

Polymers with high internal free volume patent-application, October 2002

A novel time lag method for the analysis of mixed gas diffusion in polymeric membranes by on-line mass spectrometry: Method development and validation journal, September 2018

Sorption and transport of inert gases in PVF2/PMMA blends journal, October 1986

Correlation of separation factor versus permeability for polymeric membranes journal, October 1991

Fluorinated high-performance polymers: Poly(arylene ether)s and aromatic polyimides containing trifluoromethyl groups journal, August 2010

Permeability of carbon dioxide at elevated pressures in substituted polycarbonates journal, November 1990

Gas permeation parameters and other physicochemical properties of a polymer of intrinsic microporosity: Polybenzodioxane PIM-1 journal, December 2008

Post-crosslinking of triptycene-based Tröger's base polymers with enhanced natural gas separation performance journal, June 2018

Living ring-opening metathesis polymerization journal, January 2007

Physical Aging, Plasticization and Their Effects on Gas Permeation in “Rigid” Polymers of Intrinsic Microporosity journal, August 2015

Decarboxylation-Induced Cross-Linking of Polymers of Intrinsic Microporosity (PIMs) for Membrane Gas Separation journal, June 2012

Physical aging of thin 6FDA-based polyimide membranes containing carboxyl acid groups. Part II. Optical properties journal, April 2006

The upper bound revisited journal, July 2008

Physical aging of thin glassy polymer films monitored by gas permeability journal, November 2004

Polymers with high internal free volume patent, August 2004

Compositions, methods, and systems comprising poly(thiophenes) patent, September 2014

Adsorption of Gases in Multimolecular Layers journal, February 1938

Molecular Design of Free Volume as a Route to Low-κ Dielectric Materials journal, November 2003

50th Anniversary Perspective : Polymers and Mixed Matrix Membranes for Gas and Vapor Separation: A Review and Prospective Opportunities journal, October 2017

Integrated membrane material and process development for gas separation journal, May 2014

Analysis of the transport properties of thermally rearranged (TR) polymers and polymers of intrinsic microporosity (PIM) relative to upper bound performance journal, March 2017

Plasticization-resistant glassy polyimide membranes for CO2/CO4 separations journal, August 1998

Triptycene Induced Enhancement of Membrane Gas Selectivity for Microporous Tröger's Base Polymers journal, March 2014

Gas Permeation Properties, Physical Aging, and Its Mitigation in High Free Volume Glassy Polymers journal, May 2018

Compositions, methods, and systems comprising fluorous-soluble polymers patent, October 2015

Basis of Permeability/Selectivity Tradeoff Relations in Polymeric Gas Separation Membranes journal, January 1999

The solution-diffusion model: a review journal, November 1995

Gas separation membranes from polymers of intrinsic microporosity journal, April 2005

Polymers of intrinsic microporosity (PIMs): organic materials for membrane separations, heterogeneous catalysis and hydrogen storage journal, January 2006

Polymer nanosieve membranes for CO2-capture applications journal, April 2011

Determination of Gas Transport Coefficients of Mixed Gases in 6FDA-TMPDA Polyimide by NMR Spectroscopy journal, April 2017

Mechanochemical synthesis of iptycenes patent, December 2018

Advances in high permeability polymer-based membrane materials for CO 2 separations journal, January 2016

The Effects of Crosslinking Chemistry on CO 2 Plasticization of Polyimide Gas Separation Membranes journal, November 2002

Physical aging of thin 6FDA-based polyimide membranes containing carboxyl acid groups. Part I. Transport properties journal, April 2006

Current challenges in membrane separation of CO2 from natural gas: A review journal, September 2013

Contributions of diffusion and solubility selectivity to the upper bound analysis for glassy gas separation membranes journal, March 2014

Polymers for analyte detection patent, December 2013

A Spirobifluorene-Based Polymer of Intrinsic Microporosity with Improved Performance for Gas Separation journal, September 2012

Synthesis and characterization of triptycene-based polyimides with tunable high fractional free volume for gas separation membranes journal, January 2014

Polysulfide-Blocking Microporous Polymer Membrane Tailored for Hybrid Li-Sulfur Flow Batteries journal, August 2015

Plasticization of glassy polymers by CO2 journal, June 1985

Gas permeation in thin films of “high free-volume” glassy perfluoropolymers: Part I. Physical aging journal, October 2014

Efficient Synthesis of Rigid Ladder Polymers via Palladium Catalyzed Annulation journal, December 2014

Decarboxylation-Induced Cross-Linking of a Polyimide for Enhanced CO 2 Plasticization Resistance journal, November 2008

Conditioning of Fluorine-Containing Polyimides. 2. Effect of Conditioning Protocol at 8 Volume Dilation on Gas-Transport Properties journal, May 1999

Physical aging in plastics and other glassy materials journal, March 1977

Polymer synthetic technique patent, October 2012

Elucidating the mechanism(s) of gas transport in poly[1-(trimethylsilyl)-1-propyne] (PTMSP) membranes journal, January 1994

Interactions of Carbon Dioxide with Liquid Fluorocarbons journal, December 2003

Gas permeation in thin films of “high free-volume” glassy perfluoropolymers: Part II. CO2 plasticization and sorption journal, March 2015

Emissive, high charge transport polymers patent, May 2006

Role of Intrachain Rigidity in the Plasticization of Intrinsically Microporous Triptycene-Based Polyimide Membranes in Mixed-Gas CO 2 /CH 4 Separations journal, October 2014

Microporous Materials Based on Norbornadiene-Based Cross-Linked Polymers journal, December 2018

Polymers for gas separations: the next decade journal, September 1994

Polymer of Intrinsic Microporosity Incorporating Thioamide Functionality: Preparation and Gas Transport Properties
journal, August 2011

CO2-induced plasticization phenomena in glassy polymers
journal, March 1999

Influence of methanol conditioning and physical aging on carbon spin-lattice relaxation times of poly(1-trimethylsilyl-1-propyne)
journal, November 2004

Mixed-gas permeation of syngas components in poly(dimethylsiloxane) and poly(1-trimethylsilyl-1-propyne) at elevated temperatures
journal, September 2001

Effect of Temperature on Physical Aging of Thin Glassy Polymer Films
journal, November 2005

Synthesis and gas permeation properties of novel spirobisindane-based polyimides of intrinsic microporosity
journal, January 2013

Filter materials including functionalized cellulose
patent, September 2021

Mixed gas sorption in glassy polymeric membranes: I. CO2/CH4 and n-C4/CH4 mixtures sorption in poly(1-trimethylsilyl-1-propyne) (PTMSP)
journal, January 2014

Porous Organic Polymers via Ring Opening Metathesis Polymerization
journal, February 2018

Sub-T_g Cross-Linking of a Polyimide Membrane for Enhanced CO₂ Plasticization Resistance for Natural Gas Separation
journal, August 2011

Pure- and mixed-gas permeation of CO2 and CH4 in thermally rearranged polymers based on 3,3′-dihydroxy-4,4′-diamino-biphenyl (HAB) and 2,2′-bis-(3,4-dicarboxyphenyl) hexafluoropropane dianhydride (6FDA)
journal, February 2015

Carbon dioxide plasticization of thin glassy polymer films
journal, November 2011

Emissive polymers and devices incorporating these polymers
patent, April 2007

Gas sorption and permeation in PIM-1
journal, April 2013

Avogadro: an advanced semantic chemical editor, visualization, and analysis platform
journal, August 2012

Polymers of intrinsic microporosity (PIMs): robust, solution-processable, organic nanoporous materials
journal, January 2004

An Efficient Polymer Molecular Sieve for Membrane Gas Separations
journal, January 2013

Polymers with high internal free volume
patent, February 2009

Pure- and mixed-gas permeation properties of highly selective and plasticization resistant hydroxyl-diamine-based 6FDA polyimides for CO2/CH4 separation
journal, May 2016

Effect of physical aging on the gas transport and sorption in PIM-1 membranes
journal, March 2017

Physical aging, CO 2 sorption and plasticization in thin films of polymer with intrinsic microporosity (PIM-1)
journal, September 2017

Polymer ultrapermeability from the inefficient packing of 2D chains
journal, July 2017

Polymers with high internal free volume
patent-application, October 2002

A novel time lag method for the analysis of mixed gas diffusion in polymeric membranes by on-line mass spectrometry: Method development and validation
journal, September 2018

Sorption and transport of inert gases in PVF₂/PMMA blends
journal, October 1986

Correlation of separation factor versus permeability for polymeric membranes
journal, October 1991

Fluorinated high-performance polymers: Poly(arylene ether)s and aromatic polyimides containing trifluoromethyl groups
journal, August 2010

Permeability of carbon dioxide at elevated pressures in substituted polycarbonates
journal, November 1990

Gas permeation parameters and other physicochemical properties of a polymer of intrinsic microporosity: Polybenzodioxane PIM-1
journal, December 2008

Post-crosslinking of triptycene-based Tröger's base polymers with enhanced natural gas separation performance
journal, June 2018

Living ring-opening metathesis polymerization
journal, January 2007

Physical Aging, Plasticization and Their Effects on Gas Permeation in “Rigid” Polymers of Intrinsic Microporosity
journal, August 2015

Decarboxylation-Induced Cross-Linking of Polymers of Intrinsic Microporosity (PIMs) for Membrane Gas Separation
journal, June 2012

Physical aging of thin 6FDA-based polyimide membranes containing carboxyl acid groups. Part II. Optical properties
journal, April 2006

The upper bound revisited
journal, July 2008

Physical aging of thin glassy polymer films monitored by gas permeability
journal, November 2004

Polymers with high internal free volume
patent, August 2004

Compositions, methods, and systems comprising poly(thiophenes)
patent, September 2014

Adsorption of Gases in Multimolecular Layers
journal, February 1938

Molecular Design of Free Volume as a Route to Low-κ Dielectric Materials
journal, November 2003

50th Anniversary Perspective : Polymers and Mixed Matrix Membranes for Gas and Vapor Separation: A Review and Prospective Opportunities
journal, October 2017

Integrated membrane material and process development for gas separation
journal, May 2014

Analysis of the transport properties of thermally rearranged (TR) polymers and polymers of intrinsic microporosity (PIM) relative to upper bound performance
journal, March 2017

Plasticization-resistant glassy polyimide membranes for CO2/CO4 separations
journal, August 1998

Triptycene Induced Enhancement of Membrane Gas Selectivity for Microporous Tröger's Base Polymers
journal, March 2014

Gas Permeation Properties, Physical Aging, and Its Mitigation in High Free Volume Glassy Polymers
journal, May 2018

Compositions, methods, and systems comprising fluorous-soluble polymers
patent, October 2015

Basis of Permeability/Selectivity Tradeoff Relations in Polymeric Gas Separation Membranes
journal, January 1999

The solution-diffusion model: a review
journal, November 1995

Gas separation membranes from polymers of intrinsic microporosity
journal, April 2005

Polymers of intrinsic microporosity (PIMs): organic materials for membrane separations, heterogeneous catalysis and hydrogen storage
journal, January 2006

Polymer nanosieve membranes for CO₂-capture applications
journal, April 2011

Determination of Gas Transport Coefficients of Mixed Gases in 6FDA-TMPDA Polyimide by NMR Spectroscopy
journal, April 2017

Mechanochemical synthesis of iptycenes
patent, December 2018

Advances in high permeability polymer-based membrane materials for CO ₂ separations
journal, January 2016

The Effects of Crosslinking Chemistry on CO ₂ Plasticization of Polyimide Gas Separation Membranes
journal, November 2002

Physical aging of thin 6FDA-based polyimide membranes containing carboxyl acid groups. Part I. Transport properties
journal, April 2006

Current challenges in membrane separation of CO2 from natural gas: A review
journal, September 2013

Contributions of diffusion and solubility selectivity to the upper bound analysis for glassy gas separation membranes
journal, March 2014

Polymers for analyte detection
patent, December 2013

A Spirobifluorene-Based Polymer of Intrinsic Microporosity with Improved Performance for Gas Separation
journal, September 2012

Synthesis and characterization of triptycene-based polyimides with tunable high fractional free volume for gas separation membranes
journal, January 2014

Polysulfide-Blocking Microporous Polymer Membrane Tailored for Hybrid Li-Sulfur Flow Batteries
journal, August 2015

Plasticization of glassy polymers by CO2
journal, June 1985

Gas permeation in thin films of “high free-volume” glassy perfluoropolymers: Part I. Physical aging
journal, October 2014

Efficient Synthesis of Rigid Ladder Polymers via Palladium Catalyzed Annulation
journal, December 2014

Decarboxylation-Induced Cross-Linking of a Polyimide for Enhanced CO ₂ Plasticization Resistance
journal, November 2008

Conditioning of Fluorine-Containing Polyimides. 2. Effect of Conditioning Protocol at 8 Volume Dilation on Gas-Transport Properties
journal, May 1999

Physical aging in plastics and other glassy materials
journal, March 1977

Polymer synthetic technique
patent, October 2012

Elucidating the mechanism(s) of gas transport in poly[1-(trimethylsilyl)-1-propyne] (PTMSP) membranes
journal, January 1994

Interactions of Carbon Dioxide with Liquid Fluorocarbons
journal, December 2003

Gas permeation in thin films of “high free-volume” glassy perfluoropolymers: Part II. CO2 plasticization and sorption
journal, March 2015

Emissive, high charge transport polymers
patent, May 2006

Role of Intrachain Rigidity in the Plasticization of Intrinsically Microporous Triptycene-Based Polyimide Membranes in Mixed-Gas CO ₂ /CH ₄ Separations
journal, October 2014

Microporous Materials Based on Norbornadiene-Based Cross-Linked Polymers
journal, December 2018

Polymers for gas separations: the next decade
journal, September 1994

A New Two-Constant Equation of State
journal, February 1976

Emissive compositions with internal standard and related techniques
patent, August 2014

Pure- and mixed-gas CO2/CH4 separation properties of PIM-1 and an amidoxime-functionalized PIM-1
journal, May 2014