Bio-based polymers from raw lignocellulosic biomass

Epps, Thomas H.; Holmberg, Angela L.; Nicastro, Kaleigh H.; Wang, Shu; Saha, Basudeb; Shuai, Li; Vlachos, Dionisios G.

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Title: Bio-based polymers from raw lignocellulosic biomass

Abstract

Disclosed herein is a method of making polymerizable bio-based monomers containing one phenolic hydroxyl group which has been derivatized to provide at least one polymerizable functional group which is an ethylenically unsaturated functional group (such as a [meth]acrylate group), where the precursors of the polymerizable bio-based monomers are derived from raw lignin-containing biomass. Also disclosed herein are bio-based copolymers prepared from such bio-based monomers and a co-monomer, and methods of making and using such bio-based copolymers. In particular, the bio-based copolymers can be used as pressure sensitive adhesives, binders, and polymer electrolytes.

Inventors:: Epps, III, Thomas H.; Holmberg, Angela L.; Nicastro, Kaleigh H.; Wang, Shu; Saha, Basudeb; Shuai, Li; Vlachos, Dionisios G.

Issue Date:: 2022-12-13

Research Org.:: Univ. of Delaware, Newark, DE (United States)

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

OSTI Identifier:: 1986918

Patent Number(s):: 11525024

Application Number:: 16/243,718

Assignee:: University of Delaware (Nonatum Mills, DE)

DOE Contract Number:: CHE-1507010; SC0001004; SC0014458

Resource Type:: Patent

Resource Relation:: Patent File Date: 01/09/2019

Country of Publication:: United States

Language:: English

Citation Formats


                    Epps, III, Thomas H., Holmberg, Angela L., Nicastro, Kaleigh H., Wang, Shu, Saha, Basudeb, Shuai, Li, and Vlachos, Dionisios G. Bio-based polymers from raw lignocellulosic biomass.  United States: N. p., 2022. 
        Web.

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                    Epps, III, Thomas H., Holmberg, Angela L., Nicastro, Kaleigh H., Wang, Shu, Saha, Basudeb, Shuai, Li, & Vlachos, Dionisios G. Bio-based polymers from raw lignocellulosic biomass.  United States.

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                    Epps, III, Thomas H., Holmberg, Angela L., Nicastro, Kaleigh H., Wang, Shu, Saha, Basudeb, Shuai, Li, and Vlachos, Dionisios G. Tue .  
        "Bio-based polymers from raw lignocellulosic biomass".  United States.  https://www.osti.gov/servlets/purl/1986918.

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@article{osti_1986918,

  title        = {Bio-based polymers from raw lignocellulosic biomass},

  author       = {Epps, III, Thomas H. and Holmberg, Angela L. and Nicastro, Kaleigh H. and Wang, Shu and Saha, Basudeb and Shuai, Li and Vlachos, Dionisios G.},

  abstractNote = {Disclosed herein is a method of making polymerizable bio-based monomers containing one phenolic hydroxyl group which has been derivatized to provide at least one polymerizable functional group which is an ethylenically unsaturated functional group (such as a [meth]acrylate group), where the precursors of the polymerizable bio-based monomers are derived from raw lignin-containing biomass. Also disclosed herein are bio-based copolymers prepared from such bio-based monomers and a co-monomer, and methods of making and using such bio-based copolymers. In particular, the bio-based copolymers can be used as pressure sensitive adhesives, binders, and polymer electrolytes.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {2022},

  month        = {12}

}

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Lee, Sangjun; Lee, Kyungchan; Kim, Young-Wun
ACS Sustainable Chemistry & Engineering, Vol. 3, Issue 9
https://doi.org/10.1021/acssuschemeng.5b00580

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Title: Bio-based polymers from raw lignocellulosic biomass

Abstract

Citation Formats

Bright Side of Lignin Depolymerization: Toward New Platform Chemicals journal, January 2018

Lignin Valorization: Two Hybrid Biochemical Routes for the Conversion of Polymeric Lignin into Value-added Chemicals journal, August 2017

High-Performance Pressure-Sensitive Adhesives from Renewable Triblock Copolymers journal, July 2015

Polymerization behavior of 2,6-dimethoxystyrene journal, June 1969

Repositionable pressure-sensitive adhesive tape patent, August 1992

Substituted Amide Compound patent-application, July 2012

Biochemical transformation of lignin for deriving valued commodities from lignocellulose journal, June 2017

Synthesis of poly(methyl methacrylate)-b-poly(n-butyl acrylate)-b-poly(methyl methacrylate) triblocks and their potential as thermoplastic elastomers journal, March 2000

Recent synthetic approaches and emerging bio-inspired strategies for the development of sustainable pressure-sensitive adhesives derived from renewable building blocks: ARTICLE journal, March 2014

Composites Having Leather-Like Characteristics patent-application, December 2013

Lignin-Based Bio-Oil Mimic as Biobased Resin for Composite Applications journal, February 2013

Reductive lignocellulose fractionation into soluble lignin-derived phenolic monomers and dimers and processable carbohydrate pulps journal, January 2015

The Chemistry of Stable Phenoxy Radicals journal, October 1967

Tunable Thermosetting Epoxies Based on Fractionated and Well-Characterized Lignins journal, March 2018

Catalytic Biorefining of Plant Biomass to Non-Pyrolytic Lignin Bio-Oil and Carbohydrates through Hydrogen Transfer Reactions journal, June 2014

Bio-Based Foam from Natural Oils patent-application, November 2012

Lignin Model Compounds as Bio-Based Reactive Diluents for Liquid Molding Resins journal, April 2012

Synthesis, solution properties and chain flexibility of poly(2,6-dimethylphenyl methacrylate) journal, May 1990

Monomers and Polymers Having Energy Absorbing Moieties of Use in Desorption/Ionization of Analytes patent-application, November 2003

Vanillin-based resin for use in composite applications journal, January 2012

Biobased building blocks for the rational design of renewable block polymers journal, January 2014

Polymers prepared from functionalized dimethoxyphenol monomers patent, April 2019

Lignin Depolymerization into Aromatic Monomers over Solid Acid Catalysts journal, November 2014

Hydrogenolysis of lignosulfonate into phenols over heterogeneous nickel catalysts journal, April 2012

Negative type image recording material patent, September 1999

Turning renewable resources into value-added polymer: development of lignin-based thermoplastic journal, January 2012

Structure and rheology of di- and triblock copolymers of polystyrene and poly(n-butyl acrylate) journal, March 2011

Properties of Thermosets Derived from Chemically Modified Triglycerides and Bio-Based Comonomers journal, December 2013

Selective production of 4-ethylphenolics from lignin via mild hydrogenolysis journal, August 2012

The future of reversible addition fragmentation chain transfer polymerization journal, September 2008

Determination of Solvent–Polymer and Polymer–Polymer Flory–Huggins Interaction Parameters for Poly(3-hexylthiophene) via Solvent Vapor Swelling journal, August 2013

Living Radical Polymerization by the RAFT Process journal, January 2005

Effect of Methoxy Substituent Position on Thermal Properties and Solvent Resistance of Lignin-Inspired Poly(dimethoxyphenyl methacrylate)s journal, July 2017

From models to lignin: Transition metal catalysis for selective bond cleavage reactions journal, January 2016

Softwood Lignin-Based Methacrylate Polymers with Tunable Thermal and Viscoelastic Properties journal, February 2016

Sustainable glucose-based block copolymers exhibit elastomeric and adhesive behavior journal, January 2016

Furylated Flavonoids: Fully Biobased Building Blocks Produced by Condensed Tannins Depolymerization journal, November 2017

Characteristic Ratio and Plateau Modulus of 1,2-Polybutadiene. A Comparison with Other Rubbers journal, November 1990

Biobased Epoxy Resins from Deconstructed Native Softwood Lignin journal, July 2017

Selective [2 + 2]-Cycloaddition in Methacrylic Stilbene Polymers without Interference from E/Z-Isomerization journal, November 2011

Pressure-Sensitive Adhesives: An Introductory Course journal, June 2003

Syringyl Methacrylate, a Hardwood Lignin-Based Monomer for High- T g Polymeric Materials journal, April 2016

Total synthesis of alboatrin, a phytotoxic metabolite from Verticillium alboatrum journal, March 2008

Renewable Thermoplastics Based on Lignin-Derived Polyphenols journal, April 2017

Adhesive properties of acrylate copolymers: Effect of the nature of the substrate and copolymer functionality journal, April 2012

The Influence of Hydrogen Bonding Side-Groups on Viscoelastic Behavior of Linear and Network Polymers journal, January 2014

The preparation of high conversion polymeric systems containing eugenol residues and their rheological characterization journal, November 2007

Cinchona based squaramide catalysed enantioselective Michael addition of α-nitrophosphonates to aryl acrylates: enantioselective synthesis of quaternary α-aminophosphonates journal, December 2013

Pressure-Sensitive Adhesives from Renewable Triblock Copolymers journal, January 2011

Chemistry of lignin-based materials journal, September 2013

Formaldehyde stabilization facilitates lignin monomer production during biomass depolymerization journal, October 2016

Towards high-yield lignin monomer production journal, January 2017

Thermochemical conversion of lignin to functional materials: a review and future directions journal, January 2015

Palladium-catalyzed cross-coupling reactions of highly hindered, electron-rich phenol triflates and organostannanes journal, January 1992

Novel Copolymers of Styrene. 3. Oxy Ring-disubstituted 2-cyano-3-phenyl-2-propenamides journal, January 2013

RAFT polymerization and associated reactivity ratios of methacrylate-functionalized mixed bio-oil constituents journal, January 2015

Low Ceiling Temperature in Radical Polymerization of 2, 6-Dimethylphenyl Methacrylate journal, January 1981

A Facile Method for Generating Designer Block Copolymers from Functionalized Lignin Model Compounds journal, January 2014

Chemical modification of lignins: Towards biobased polymers journal, July 2014

Acrylic Triblock Copolymers Incorporating Isosorbide for Pressure Sensitive Adhesives journal, May 2016

Fast pyrolysis of Kraft lignin—Vapor cracking over various fixed-bed catalysts journal, March 2013

Model hydrocarbon polymers: rheological properties of linear polyisoprenes and hydrogenated polyisoprenes journal, December 1984

Bio-Based Block Polymers Derived from Lignin and Fatty Acids patent-application, September 2014

The effect of molecular weight and temperature on tack properties of model polyisobutylenes journal, August 2004

High modulus polymers and composites from plant oils patent, September 2000

Medical Devices Having Bioactive Surfaces patent-application, November 2007

Methods and Compositions for Control of Cabbage Looper, Trichoplusia Ni patent-application, May 2013

Fatty acid monomers to reduce emissions and toughen polymers patent, April 2009

Tack and viscoelastic properties of an acrylic block copolymer/tackifier system journal, December 2009

Biphasic extraction of mechanocatalytically-depolymerized lignin from water-soluble wood and its catalytic downstream processing journal, January 2017

Preparation and Characterization of a Renewable Pressure-Sensitive Adhesive System Derived from ε-Decalactone, l -Lactide, Epoxidized Soybean Oil, and Rosin Ester journal, August 2015

Bright Side of Lignin Depolymerization: Toward New Platform Chemicals
journal, January 2018

Lignin Valorization: Two Hybrid Biochemical Routes for the Conversion of Polymeric Lignin into Value-added Chemicals
journal, August 2017

High-Performance Pressure-Sensitive Adhesives from Renewable Triblock Copolymers
journal, July 2015

Polymerization behavior of 2,6-dimethoxystyrene
journal, June 1969

Repositionable pressure-sensitive adhesive tape
patent, August 1992

Substituted Amide Compound
patent-application, July 2012

Biochemical transformation of lignin for deriving valued commodities from lignocellulose
journal, June 2017

Synthesis of poly(methyl methacrylate)-b-poly(n-butyl acrylate)-b-poly(methyl methacrylate) triblocks and their potential as thermoplastic elastomers
journal, March 2000

Recent synthetic approaches and emerging bio-inspired strategies for the development of sustainable pressure-sensitive adhesives derived from renewable building blocks: ARTICLE
journal, March 2014

Composites Having Leather-Like Characteristics
patent-application, December 2013

Lignin-Based Bio-Oil Mimic as Biobased Resin for Composite Applications
journal, February 2013

Reductive lignocellulose fractionation into soluble lignin-derived phenolic monomers and dimers and processable carbohydrate pulps
journal, January 2015

The Chemistry of Stable Phenoxy Radicals
journal, October 1967

Tunable Thermosetting Epoxies Based on Fractionated and Well-Characterized Lignins
journal, March 2018

Catalytic Biorefining of Plant Biomass to Non-Pyrolytic Lignin Bio-Oil and Carbohydrates through Hydrogen Transfer Reactions
journal, June 2014

Bio-Based Foam from Natural Oils
patent-application, November 2012

Lignin Model Compounds as Bio-Based Reactive Diluents for Liquid Molding Resins
journal, April 2012

Synthesis, solution properties and chain flexibility of poly(2,6-dimethylphenyl methacrylate)
journal, May 1990

Monomers and Polymers Having Energy Absorbing Moieties of Use in Desorption/Ionization of Analytes
patent-application, November 2003

Vanillin-based resin for use in composite applications
journal, January 2012

Biobased building blocks for the rational design of renewable block polymers
journal, January 2014

Polymers prepared from functionalized dimethoxyphenol monomers
patent, April 2019

Lignin Depolymerization into Aromatic Monomers over Solid Acid Catalysts
journal, November 2014

Hydrogenolysis of lignosulfonate into phenols over heterogeneous nickel catalysts
journal, April 2012

Negative type image recording material
patent, September 1999

Turning renewable resources into value-added polymer: development of lignin-based thermoplastic
journal, January 2012

Structure and rheology of di- and triblock copolymers of polystyrene and poly(n-butyl acrylate)
journal, March 2011

Properties of Thermosets Derived from Chemically Modified Triglycerides and Bio-Based Comonomers
journal, December 2013

Selective production of 4-ethylphenolics from lignin via mild hydrogenolysis
journal, August 2012

The future of reversible addition fragmentation chain transfer polymerization
journal, September 2008

Determination of Solvent–Polymer and Polymer–Polymer Flory–Huggins Interaction Parameters for Poly(3-hexylthiophene) via Solvent Vapor Swelling
journal, August 2013

Living Radical Polymerization by the RAFT Process
journal, January 2005

Effect of Methoxy Substituent Position on Thermal Properties and Solvent Resistance of Lignin-Inspired Poly(dimethoxyphenyl methacrylate)s
journal, July 2017

From models to lignin: Transition metal catalysis for selective bond cleavage reactions
journal, January 2016

Softwood Lignin-Based Methacrylate Polymers with Tunable Thermal and Viscoelastic Properties
journal, February 2016

Sustainable glucose-based block copolymers exhibit elastomeric and adhesive behavior
journal, January 2016

Furylated Flavonoids: Fully Biobased Building Blocks Produced by Condensed Tannins Depolymerization
journal, November 2017

Characteristic Ratio and Plateau Modulus of 1,2-Polybutadiene. A Comparison with Other Rubbers
journal, November 1990

Biobased Epoxy Resins from Deconstructed Native Softwood Lignin
journal, July 2017

Selective [2 + 2]-Cycloaddition in Methacrylic Stilbene Polymers without Interference from E/Z-Isomerization
journal, November 2011

Pressure-Sensitive Adhesives: An Introductory Course
journal, June 2003

Syringyl Methacrylate, a Hardwood Lignin-Based Monomer for High- T _g Polymeric Materials
journal, April 2016

Total synthesis of alboatrin, a phytotoxic metabolite from Verticillium alboatrum
journal, March 2008

Renewable Thermoplastics Based on Lignin-Derived Polyphenols
journal, April 2017

Adhesive properties of acrylate copolymers: Effect of the nature of the substrate and copolymer functionality
journal, April 2012

The Influence of Hydrogen Bonding Side-Groups on Viscoelastic Behavior of Linear and Network Polymers
journal, January 2014

The preparation of high conversion polymeric systems containing eugenol residues and their rheological characterization
journal, November 2007

Cinchona based squaramide catalysed enantioselective Michael addition of α-nitrophosphonates to aryl acrylates: enantioselective synthesis of quaternary α-aminophosphonates
journal, December 2013

Pressure-Sensitive Adhesives from Renewable Triblock Copolymers
journal, January 2011

Chemistry of lignin-based materials
journal, September 2013

Formaldehyde stabilization facilitates lignin monomer production during biomass depolymerization
journal, October 2016

Towards high-yield lignin monomer production
journal, January 2017

Thermochemical conversion of lignin to functional materials: a review and future directions
journal, January 2015

Palladium-catalyzed cross-coupling reactions of highly hindered, electron-rich phenol triflates and organostannanes
journal, January 1992

Novel Copolymers of Styrene. 3. Oxy Ring-disubstituted 2-cyano-3-phenyl-2-propenamides
journal, January 2013

RAFT polymerization and associated reactivity ratios of methacrylate-functionalized mixed bio-oil constituents
journal, January 2015

Low Ceiling Temperature in Radical Polymerization of 2, 6-Dimethylphenyl Methacrylate
journal, January 1981

A Facile Method for Generating Designer Block Copolymers from Functionalized Lignin Model Compounds
journal, January 2014

Chemical modification of lignins: Towards biobased polymers
journal, July 2014

Acrylic Triblock Copolymers Incorporating Isosorbide for Pressure Sensitive Adhesives
journal, May 2016

Fast pyrolysis of Kraft lignin—Vapor cracking over various fixed-bed catalysts
journal, March 2013

Model hydrocarbon polymers: rheological properties of linear polyisoprenes and hydrogenated polyisoprenes
journal, December 1984

Bio-Based Block Polymers Derived from Lignin and Fatty Acids
patent-application, September 2014

The effect of molecular weight and temperature on tack properties of model polyisobutylenes
journal, August 2004

High modulus polymers and composites from plant oils
patent, September 2000

Medical Devices Having Bioactive Surfaces
patent-application, November 2007

Methods and Compositions for Control of Cabbage Looper, Trichoplusia Ni
patent-application, May 2013

Fatty acid monomers to reduce emissions and toughen polymers
patent, April 2009

Tack and viscoelastic properties of an acrylic block copolymer/tackifier system
journal, December 2009

Biphasic extraction of mechanocatalytically-depolymerized lignin from water-soluble wood and its catalytic downstream processing
journal, January 2017

Preparation and Characterization of a Renewable Pressure-Sensitive Adhesive System Derived from ε-Decalactone, l -Lactide, Epoxidized Soybean Oil, and Rosin Ester
journal, August 2015