Lignin-based vitrimers: valorization and utilization of lignin in high-value applications

Karoki, Peter K.; Zhang, Shuyang; Pu, Yunqiao; Ragauskas, Arthur J.

doi:10.1039/D4MA00281D

Title: Lignin-based vitrimers: valorization and utilization of lignin in high-value applications

Journal Article · 01 January 2024 · Materials Advances

DOI: https://doi.org/10.1039/D4MA00281D · OSTI ID:2403590

^[1];

^[2];

^[3]

Department of Chemical & Biomolecular Engineering, University of Tennessee Knoxville, Knoxville, TN 37996, USA
Joint Institute for Biological Sciences, Biosciences Division, Oak Ridge National Laboratory, Oak Ridge, TN 37831, USA
Department of Chemical & Biomolecular Engineering, University of Tennessee Knoxville, Knoxville, TN 37996, USA, Center for Renewable Carbon, The University of Tennessee Knoxville, Institute of Agriculture, Knoxville, TN 37996, USA, Joint Institute for Biological Sciences, Biosciences Division, Oak Ridge National Laboratory, Oak Ridge, TN 37831, USA

We review recent advances in the utilization of lignin as a viable alternative to fossil-based feedstock in the synthesis of a wide range of vitrimeric materials targeted towards the achievement of a sustainable and circular economy.

View Journal Article

Cite

Export

Save

Sponsoring Organization:: USDOE

OSTI ID:: 2403590

Journal Information:: Materials Advances, Journal Name: Materials Advances; ISSN MAADC9; ISSN 2633-5409

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

References (121)

Vinylogous Urethane Vitrimers Denissen, Wim; Rivero, Guadalupe; Nicolaÿ, Renaud Advanced Functional Materials, Vol. 25, Issue 16 https://doi.org/10.1002/adfm.201404553	journal	March 2015
Lignin‐Based Materials for Additive Manufacturing: Chemistry, Processing, Structures, Properties, and Applications Jiang, Bo; Jiao, Huan; Guo, Xinyu Advanced Science, Vol. 10, Issue 9 https://doi.org/10.1002/advs.202206055	journal	January 2023
Paving the Way for Lignin Valorisation: Recent Advances in Bioengineering, Biorefining and Catalysis Rinaldi, Roberto; Jastrzebski, Robin; Clough, Matthew T. Angewandte Chemie International Edition, Vol. 55, Issue 29 https://doi.org/10.1002/anie.201510351	journal	June 2016
Covalent Adaptable Networks with Tunable Exchange Rates Based on Reversible Thiol–yne Cross‐Linking Van Herck, Niels; Maes, Diederick; Unal, Kamil Angewandte Chemie International Edition, Vol. 59, Issue 9 https://doi.org/10.1002/anie.201912902	journal	January 2020
Characterization and analysis of the molecular weight of lignin for biorefining studies Tolbert, Allison; Akinosho, Hannah; Khunsupat, Ratayakorn Biofuels, Bioproducts and Biorefining, Vol. 8, Issue 6 https://doi.org/10.1002/bbb.1500	journal	June 2014
Production and Application of Lignosulfonates and Sulfonated Lignin Aro, Thomas; Fatehi, Pedram ChemSusChem, Vol. 10, Issue 9 https://doi.org/10.1002/cssc.201700082	journal	April 2017
A High‐Lignin‐Content, Removable, and Glycol‐Assisted Repairable Coating Based on Dynamic Covalent Bonds Hao, Cheng; Liu, Tuan; Zhang, Shuai ChemSusChem, Vol. 12, Issue 5 https://doi.org/10.1002/cssc.201802615	journal	February 2019
Recent Advances in the Catalytic Depolymerization of Lignin towards Phenolic Chemicals: A Review Liu, Xudong; Bouxin, Florent P.; Fan, Jiajun ChemSusChem, Vol. 13, Issue 17 https://doi.org/10.1002/cssc.202001213	journal	August 2020
Biomass Fractionation and Lignin Fractionation towards Lignin Valorization Xu, Jiayun; Li, Chenyu; Dai, Lin ChemSusChem, Vol. 13, Issue 17 https://doi.org/10.1002/cssc.202001491	journal	July 2020
Solventless Amination of Lignin and Natural Phenolics using 2‐Oxazolidinone Liu, Li‐Yang; Wan, Xue; Chen, Siwei ChemSusChem, Vol. 16, Issue 15 https://doi.org/10.1002/cssc.202300276	journal	June 2023
From Lignins to Renewable Aromatic Vitrimers based on Vinylogous Urethane Sougrati, Lisa; Duval, Antoine; Avérous, Luc ChemSusChem, Vol. 16, Issue 23 https://doi.org/10.1002/cssc.202300792	journal	September 2023
Fully Biobased Vitrimers: Future Direction toward Sustainable Cross‐Linked Polymers Vidil, Thomas; Llevot, Audrey Macromolecular Chemistry and Physics, Vol. 223, Issue 13 https://doi.org/10.1002/macp.202100494	journal	February 2022
Carboxylated Lignin as an Effective Cohardener for Enhancing Strength and Toughness of Epoxy Sun, Jiaotong; Wang, Cun; Stubbs, Ludger P. Macromolecular Materials and Engineering, Vol. 302, Issue 12 https://doi.org/10.1002/mame.201700341	journal	October 2017
Synthesis of amphiphilic polyacetal by polycondensation of aldehyde and polyethylene glycol as an acid‐labile polymer for controlled release of aldehyde Wang, Yanmei; Morinaga, Hisatoyo; Sudo, Atsushi Journal of Polymer Science Part A: Polymer Chemistry, Vol. 49, Issue 3 https://doi.org/10.1002/pola.24425	journal	December 2010
Conversion of technical lignins to functional materials with retained polymeric properties Matsushita, Yasuyuki Journal of Wood Science, Vol. 61, Issue 3 https://doi.org/10.1007/s10086-015-1470-2	journal	April 2015
A review on organosolv pretreatment of softwood with a focus on enzymatic hydrolysis of cellulose Vaidya, Alankar A.; Murton, Karl D.; Smith, Dawn A. Biomass Conversion and Biorefinery, Vol. 12, Issue 11 https://doi.org/10.1007/s13399-022-02373-9	journal	February 2022
Lignin-based epoxy composite vitrimers with light-controlled remoldability Zheng, Yong; Liu, Tingting; He, Haodong Advanced Composites and Hybrid Materials, Vol. 6, Issue 1 https://doi.org/10.1007/s42114-023-00633-4	journal	February 2023
Lignin biorefinery: Lignin source, isolation, characterization, and bioconversion Liu, Jun; Li, Xiang; Li, Mi Advances in Bioenergy https://doi.org/10.1016/bs.aibe.2022.05.004	book	January 2022
Isolation of lignin by organosolv process from different varieties of rice husk: Understanding their physical and chemical properties Singh, Sandip K.; Dhepe, Paresh L. Bioresource Technology, Vol. 221 https://doi.org/10.1016/j.biortech.2016.09.042	journal	December 2016
Cosolvent enhanced lignocellulosic fractionation tailoring lignin chemistry and enhancing lignin bioconversion Zhao, Zhi-Min; Meng, Xianzhi; Scheidemantle, Brent Bioresource Technology, Vol. 347 https://doi.org/10.1016/j.biortech.2021.126367	journal	March 2022
Vitrimers based on bio-derived chemicals: Overview and future prospects Krishnakumar, Balaji; Pucci, Andrea; Wadgaonkar, Prakash P. Chemical Engineering Journal, Vol. 433 https://doi.org/10.1016/j.cej.2021.133261	journal	April 2022
Lignin-based benzoxazines: A tunable key-precursor for the design of hydrophobic coatings, fire resistant materials and catalyst-free vitrimers Adjaoud, Antoine; Puchot, Laura; Federico, Carlos Eloy Chemical Engineering Journal, Vol. 453 https://doi.org/10.1016/j.cej.2022.139895	journal	February 2023
Economical concerns of lignin in the energy sector Sharma, Archita; Kaur, Pritam; Singh, Gursharan Cleaner Engineering and Technology, Vol. 4 https://doi.org/10.1016/j.clet.2021.100258	journal	October 2021
Facile synthesis of polyethylene-modified asphalt by chain end-functionalization Li, Mengru; Chen, Xi; Cong, Peiliang Composites Communications, Vol. 30 https://doi.org/10.1016/j.coco.2022.101088	journal	February 2022
Asphalt/polyethylene blends: Rheological properties, microstructure and viscosity modeling Vargas, María A.; Vargas, Miguel A.; Sánchez-Sólis, Antonio Construction and Building Materials, Vol. 45 https://doi.org/10.1016/j.conbuildmat.2013.03.064	journal	August 2013
Vanillin-based degradable epoxy vitrimers: Reprocessability and mechanical properties study Yu, Qingqing; Peng, Xionghou; Wang, Yuli European Polymer Journal, Vol. 117 https://doi.org/10.1016/j.eurpolymj.2019.04.053	journal	August 2019
Scalable and facile synthesis of acetal covalent adaptable networks with readily adjustable properties Lu, Na; Li, Qiong; Ma, Songqi European Polymer Journal, Vol. 147 https://doi.org/10.1016/j.eurpolymj.2021.110291	journal	March 2021
Preparation of carboxylated lignin-based epoxy resin with excellent mechanical properties Zhang, Yongjian; Wang, Hao; Eberhardt, Thomas L. European Polymer Journal, Vol. 150 https://doi.org/10.1016/j.eurpolymj.2021.110389	journal	May 2021
Comparative study on the adhesive properties of different epoxy resins Prolongo, Silvia G.; del Rosario, Gilberto; Ureña, Alejandro International Journal of Adhesion and Adhesives, Vol. 26, Issue 3 https://doi.org/10.1016/j.ijadhadh.2005.02.004	journal	June 2006
Synthesis and characterization of aminated lignin Pan, Hong; Sun, Gang; Zhao, Tao International Journal of Biological Macromolecules, Vol. 59 https://doi.org/10.1016/j.ijbiomac.2013.04.049	journal	August 2013
Amination of biorefinery technical lignin by Mannich reaction for preparing highly efficient nitrogen fertilizer Jiao, Gao-Jie; Peng, Pai; Sun, Shao-Long International Journal of Biological Macromolecules, Vol. 127 https://doi.org/10.1016/j.ijbiomac.2019.01.076	journal	April 2019
One-step silanization and amination of lignin and its adsorption of Congo red and Cu(II) ions in aqueous solution An, Liangliang; Si, Chuanling; Bae, Jin Ho International Journal of Biological Macromolecules, Vol. 159 https://doi.org/10.1016/j.ijbiomac.2020.05.072	journal	September 2020
Review of current and future softwood kraft lignin process chemistry Chakar, Fadi S.; Ragauskas, Arthur J. Industrial Crops and Products, Vol. 20, Issue 2 https://doi.org/10.1016/j.indcrop.2004.04.016	journal	September 2004
A concise review of current lignin production, applications, products and their environmental impact Bajwa, D. S.; Pourhashem, G.; Ullah, A. H. Industrial Crops and Products, Vol. 139 https://doi.org/10.1016/j.indcrop.2019.111526	journal	November 2019
Sustainable alternative for bisphenol A epoxy resin high-performance and recyclable lignin-based epoxy vitrimers Xue, Bailiang; Tang, Rui; Xue, Danwei Industrial Crops and Products, Vol. 168 https://doi.org/10.1016/j.indcrop.2021.113583	journal	September 2021
Chemical and structural characterization of hardwood and softwood LignoForce™ lignins Suota, Maria Juliane; da Silva, Thiago Alessandre; Zawadzki, Sônia Faria Industrial Crops and Products, Vol. 173 https://doi.org/10.1016/j.indcrop.2021.114138	journal	December 2021
Preparation and characterization of aminated co-solvent enhanced lignocellulosic fractionation lignin as a renewable building block for the synthesis of non-isocyanate polyurethanes Meng, Xianzhi; Zhang, Shuyang; Scheidemantle, Brent Industrial Crops and Products, Vol. 178 https://doi.org/10.1016/j.indcrop.2022.114579	journal	April 2022
Lignin-based vitrimer for circulation in plastics, coatings, and adhesives with tough mechanical properties, catalyst-free and good chemical solvent resistance Du, Liuping; Jin, Xin; Qian, Gang Industrial Crops and Products, Vol. 187 https://doi.org/10.1016/j.indcrop.2022.115439	journal	November 2022
A review on recent approaches to sustainable bio-based epoxy vitrimer from epoxidized vegetable oils Chong, K. L.; Lai, J. C.; Rahman, R. A. Industrial Crops and Products, Vol. 189 https://doi.org/10.1016/j.indcrop.2022.115857	journal	December 2022
Preparation and properties of lignin-based vitrimer system containing dynamic covalent bonds for reusable and recyclable epoxy asphalt Song, Panpan; Du, Liuping; Pang, Jiuyin Industrial Crops and Products, Vol. 197 https://doi.org/10.1016/j.indcrop.2023.116498	journal	July 2023
Vitrimers: Current research trends and their emerging applications Zheng, Jie; Png, Zhuang Mao; Ng, Shi Hoe Materials Today, Vol. 51 https://doi.org/10.1016/j.mattod.2021.07.003	journal	December 2021
Characterization of milled wood lignin and ethanol organosolv lignin from miscanthus El Hage, Roland; Brosse, Nicolas; Chrusciel, Laurent Polymer Degradation and Stability, Vol. 94, Issue 10 https://doi.org/10.1016/j.polymdegradstab.2009.07.007	journal	October 2009
Chemically recyclable polyurethanes based on bio-renewable γ-butyrolactone: From thermoplastics to elastomers Yuan, Liyun; Zhou, Wei; Shen, Yong Polymer Degradation and Stability, Vol. 204 https://doi.org/10.1016/j.polymdegradstab.2022.110116	journal	October 2022
Chemical modification of organosolv lignin using boronic acid-containing reagents Korich, Andrew L.; Fleming, Andrew B.; Walker, Amanda R. Polymer, Vol. 53, Issue 1 https://doi.org/10.1016/j.polymer.2011.10.062	journal	January 2012
Dynamic covalent polymers: Reorganizable polymers with dynamic covalent bonds Maeda, Takeshi; Otsuka, Hideyuki; Takahara, Atsushi Progress in Polymer Science, Vol. 34, Issue 7, p. 581-604 https://doi.org/10.1016/j.progpolymsci.2009.03.001	journal	July 2009
Sustainable polymers from biomass: Bridging chemistry with materials and processing Wang, Zhongkai; Ganewatta, Mitra S.; Tang, Chuanbing Progress in Polymer Science, Vol. 101 https://doi.org/10.1016/j.progpolymsci.2019.101197	journal	February 2020
Biobased vitrimers: Towards sustainable and adaptable performing polymer materials Lucherelli, Matteo Andrea; Duval, Antoine; Avérous, Luc Progress in Polymer Science, Vol. 127 https://doi.org/10.1016/j.progpolymsci.2022.101515	journal	April 2022
Biobased Epoxy Resins from Deconstructed Native Softwood Lignin van de Pas, Daniel J.; Torr, Kirk M. Biomacromolecules, Vol. 18, Issue 8 https://doi.org/10.1021/acs.biomac.7b00767	journal	July 2017
Fast Reprocessing of Acetal Covalent Adaptable Networks with High Performance Enabled by Neighboring Group Participation Li, Qiong; Ma, Songqi; Li, Pengyun Macromolecules, Vol. 54, Issue 18 https://doi.org/10.1021/acs.macromol.1c01046	journal	September 2021
Dynamic Covalent Polymer Networks Based on Degenerative Imine Bond Exchange: Tuning the Malleability and Self-Healing Properties by Solvent Chao, Albert; Negulescu, Ioan; Zhang, Donghui Macromolecules, Vol. 49, Issue 17 https://doi.org/10.1021/acs.macromol.6b01443	journal	August 2016
Catechol-Mediated Glycidylation toward Epoxy Vitrimers/Polymers with Tunable Properties Zhao, Shou; Abu-Omar, Mahdi M. Macromolecules, Vol. 52, Issue 10 https://doi.org/10.1021/acs.macromol.9b00334	journal	May 2019
Selective Cleavage of Lignin Model Compounds via a Reverse Biosynthesis Mechanism Suh, Sang Mi; Jambu, Subramanian; Chin, Mason T. Organic Letters, Vol. 25, Issue 26 https://doi.org/10.1021/acs.orglett.3c01416	journal	June 2023
New Kind of Lignin/Polyhydroxyurethane Composite: Green Synthesis, Smart Properties, Promising Applications, and Good Reprocessability and Recyclability Zhao, Wei; Liang, Zhenhua; Feng, Zihao ACS Applied Materials & Interfaces, Vol. 13, Issue 24 https://doi.org/10.1021/acsami.1c06822	journal	June 2021
Catalyst-Free Synthesis of Lignin Vitrimers with Tunable Mechanical Properties: Circular Polymers and Recoverable Adhesives Moreno, Adrian; Morsali, Mohammad; Sipponen, Mika H. ACS Applied Materials & Interfaces, Vol. 13, Issue 48 https://doi.org/10.1021/acsami.1c17412	journal	November 2021
Recyclable and Flexible Polyester Thermosets Derived from Microwave-Processed Lignin Xu, Yunsheng; Odelius, Karin; Hakkarainen, Minna ACS Applied Polymer Materials, Vol. 2, Issue 5 https://doi.org/10.1021/acsapm.0c00130	journal	April 2020
Biobased, Biodegradable, Self-Healing Boronic Ester Vitrimers from Epoxidized Soybean Oil Acrylate Zych, Arkadiusz; Tellers, Jonathan; Bertolacci, Laura ACS Applied Polymer Materials, Vol. 3, Issue 2 https://doi.org/10.1021/acsapm.0c01335	journal	December 2020
Regulating Lignin-Based Epoxy Vitrimer Performance by Fine-Tuning the Lignin Structure Tang, Rui; Xue, Bailiang; Tan, Jiaojun ACS Applied Polymer Materials, Vol. 4, Issue 2 https://doi.org/10.1021/acsapm.1c01541	journal	January 2022
Reprocessable Cross-Linked Polymer Networks: Are Associative Exchange Mechanisms Desirable? Elling, Benjamin R.; Dichtel, William R. ACS Central Science, Vol. 6, Issue 9 https://doi.org/10.1021/acscentsci.0c00567	journal	July 2020
100th Anniversary of Macromolecular Science Viewpoint: Polymers from Lignocellulosic Biomass. Current Challenges and Future Opportunities O’Dea, Robert M.; Willie, Jordan A.; Epps, Thomas H. ACS Macro Letters, Vol. 9, Issue 4 https://doi.org/10.1021/acsmacrolett.0c00024	journal	March 2020
Biobased Nonisocyanate Polyurethanes as Recyclable and Intrinsic Self-Healing Coating with Triple Healing Sites Choong, Ping Sen; Chong, Ning Xi; Wai Tam, Eric Kwok ACS Macro Letters, Vol. 10, Issue 5 https://doi.org/10.1021/acsmacrolett.1c00163	journal	May 2021
Novel and Integrated Process for the Valorization of Kraft Lignin to Produce Lignin-Containing Vitrimers More, Ajinkya; Elder, Thomas; Pajer, Nicolò ACS Omega, Vol. 8, Issue 1 https://doi.org/10.1021/acsomega.2c06445	journal	December 2022
Synthesis, Characterization, and Utilization of a Lignin-Based Adsorbent for Effective Removal of Azo Dye from Aqueous Solution Meng, Xianzhi; Scheidemantle, Brent; Li, Mi ACS Omega, Vol. 5, Issue 6 https://doi.org/10.1021/acsomega.9b03717	journal	February 2020
Fully Biobased Vitrimers from Glycyrrhizic Acid and Soybean Oil for Self-Healing, Shape Memory, Weldable, and Recyclable Materials Wu, Jianqiao; Yu, Xia; Zhang, Hao ACS Sustainable Chemistry & Engineering, Vol. 8, Issue 16 https://doi.org/10.1021/acssuschemeng.0c01047	journal	April 2020
Lignin Monomers from beyond the Canonical Monolignol Biosynthetic Pathway: Another Brick in the Wall del Río, José C.; Rencoret, Jorge; Gutiérrez, Ana ACS Sustainable Chemistry & Engineering, Vol. 8, Issue 13 https://doi.org/10.1021/acssuschemeng.0c01109	journal	March 2020
Perspective on Technical Lignin Fractionation Sadeghifar, Hasan; Ragauskas, Arthur ACS Sustainable Chemistry & Engineering, Vol. 8, Issue 22 https://doi.org/10.1021/acssuschemeng.0c01348	journal	May 2020
Lignin: A Review on Structure, Properties, and Applications as a Light-Colored UV Absorber Zhang, Yi; Naebe, Maryam ACS Sustainable Chemistry & Engineering, Vol. 9, Issue 4 https://doi.org/10.1021/acssuschemeng.0c06998	journal	January 2021
New Mechanistic Insights into the Lignin β-O-4 Linkage Acidolysis with Ethylene Glycol Stabilization Aided by Multilevel Computational Chemistry De Santi, Alessandra; Monti, Susanna; Barcaro, Giovanni ACS Sustainable Chemistry & Engineering, Vol. 9, Issue 5 https://doi.org/10.1021/acssuschemeng.0c08901	journal	January 2021
Fractionation of Lignin with Decreased Heterogeneity: Based on a Detailed Characteristics Study of Sequentially Extracted Softwood Kraft Lignin Liu, Rui; Smeds, Annika; Wang, Luyao ACS Sustainable Chemistry & Engineering, Vol. 9, Issue 41 https://doi.org/10.1021/acssuschemeng.1c04725	journal	October 2021
Starch-Reinforced Vinylogous Urethane Vitrimer Composites: An Approach to Biobased, Reprocessable, and Biodegradable Materials Haida, Philipp; Chirachanchai, Suwabun; Abetz, Volker ACS Sustainable Chemistry & Engineering, Vol. 11, Issue 22 https://doi.org/10.1021/acssuschemeng.3c01340	journal	May 2023
Synthesis and Characterization of Bio-based Epoxy Resins Derived from Vanillyl Alcohol Hernandez, Eric D.; Bassett, Alexander W.; Sadler, Joshua M. ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 8 https://doi.org/10.1021/acssuschemeng.6b00835	journal	July 2016
Effect of Fatty Acid Esterification on the Thermal Properties of Softwood Kraft Lignin Koivu, Klaus A. Y.; Sadeghifar, Hasan; Nousiainen, Paula A. ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 10 https://doi.org/10.1021/acssuschemeng.6b01048	journal	August 2016
Vanillin-Based Polyschiff Vitrimers: Reprocessability and Chemical Recyclability Geng, Hongwei; Wang, Yuli; Yu, Qingqing ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 11 https://doi.org/10.1021/acssuschemeng.8b03925	journal	September 2018
Valorization of Pyrolysis Liquids: Ozonation of the Pyrolytic Lignin Fraction and Model Components Figueirêdo, Monique B.; Deuss, Peter J.; Venderbosch, Robbie H. ACS Sustainable Chemistry & Engineering, Vol. 7, Issue 5 https://doi.org/10.1021/acssuschemeng.8b04856	journal	February 2019
Efficient Depolymerization of Lignin to Biobased Chemicals Using a Two-Step Approach Involving Ozonation in a Continuous Flow Microreactor Followed by Catalytic Hydrotreatment Figueirêdo, M. B.; Keij, F. W.; Hommes, A. ACS Sustainable Chemistry & Engineering, Vol. 7, Issue 22 https://doi.org/10.1021/acssuschemeng.9b04020	journal	October 2019
Preserving Aryl Ether Linkages and Higher Yields of Isolated Lignin through Biomass Fibrillation Bhagia, Samarthya; Ragauskas, Arthur J. ACS Sustainable Chemistry & Engineering, Vol. 8, Issue 1 https://doi.org/10.1021/acssuschemeng.9b06390	journal	December 2019
Methods for Pretreatment of Lignocellulosic Biomass for Efficient Hydrolysis and Biofuel Production Kumar, Parveen; Barrett, Diane M.; Delwiche, Michael J. Industrial & Engineering Chemistry Research, Vol. 48, Issue 8, p. 3713-3729 https://doi.org/10.1021/ie801542g	journal	April 2009
Boronic Ester Based Vitrimers with Enhanced Stability via Internal Boron–Nitrogen Coordination Zhang, Xiaoting; Wang, Shujuan; Jiang, Zikang Journal of the American Chemical Society, Vol. 142, Issue 52 https://doi.org/10.1021/jacs.0c10244	journal	December 2020
Comparative Evaluation of Three Lignin Isolation Protocols for Various Wood Species Guerra, Anderson; Filpponen, Ilari; Lucia, Lucian A. Journal of Agricultural and Food Chemistry, Vol. 54, Issue 26 https://doi.org/10.1021/jf062433c	journal	December 2006
Pendent Chain Functionalized Polyacetals That Display pH-Dependent Degradation: A Platform for the Development of Novel Polymer Therapeutics Tomlinson, Ryan; Klee, Marcus; Garrett, Shane Macromolecules, Vol. 35, Issue 2 https://doi.org/10.1021/ma0108867	journal	December 2001
PEG-based Multifunctional Polyethers with Highly Reactive Vinyl-Ether Side Chains for Click-Type Functionalization Mangold, Christine; Dingels, Carsten; Obermeier, Boris Macromolecules, Vol. 44, Issue 16 https://doi.org/10.1021/ma200898n	journal	August 2011
One-Pot Synthesis and PEGylation of Hyperbranched Polyacetals with a Degree of Branching of 100% Liu, Na; Vignolle, Joan; Vincent, Jean-Marc Macromolecules, Vol. 47, Issue 5 https://doi.org/10.1021/ma4026509	journal	February 2014
Chemical Modification of a Lignin Model Polymer via Arylboronate Ester Formation under Mild Reaction Conditions Korich, Andrew L.; Clarke, Kristine M.; Wallace, David Macromolecules, Vol. 42, Issue 16 https://doi.org/10.1021/ma901146b	journal	July 2009
Covalent Adaptable Networks (CANs): A Unique Paradigm in Cross-Linked Polymers Kloxin, Christopher J.; Scott, Timothy F.; Adzima, Brian J. Macromolecules, Vol. 43, Issue 6 https://doi.org/10.1021/ma902596s	journal	March 2010
Mechanochromic and thermally reprocessable thermosets for autonomic damage reporting and self-healing coatings Yoon, Subin; Choi, Jong Ho; Sung, Bong June NPG Asia Materials, Vol. 14, Issue 1 https://doi.org/10.1038/s41427-022-00406-3	journal	July 2022
Application of quantitative 31P NMR in biomass lignin and biofuel precursors characterization Pu, Yunqiao; Cao, Shilin; Ragauskas, Arthur J. Energy & Environmental Science, Vol. 4, Issue 9 https://doi.org/10.1039/c1ee01201k	journal	January 2011
Oxidative conversion of lignin and lignin model compounds catalyzed by CeO ₂ -supported Pd nanoparticles Deng, Weiping; Zhang, Hongxi; Wu, Xuejiao Green Chemistry, Vol. 17, Issue 11 https://doi.org/10.1039/c5gc01473e	journal	January 2015
Towards lignin-based functional materials in a sustainable world Kai, Dan; Tan, Mein Jin; Chee, Pei Lin Green Chemistry, Vol. 18, Issue 5 https://doi.org/10.1039/c5gc02616d	journal	January 2016
Vitrimers: permanent organic networks with glass-like fluidity Denissen, Wim; Winne, Johan M.; Du Prez, Filip E. Chemical Science, Vol. 7, Issue 1 https://doi.org/10.1039/c5sc02223a	journal	January 2016
Chemical modifications of lignin for the preparation of macromers containing cyclic carbonates Salanti, Anika; Zoia, Luca; Orlandi, Marco Green Chemistry, Vol. 18, Issue 14 https://doi.org/10.1039/c6gc01028h	journal	January 2016
Self-healing of glucose-modified polyurethane networks facilitated by damage-induced primary amines Yang, Ying; Urban, Marek W. Polymer Chemistry, Vol. 8, Issue 1 https://doi.org/10.1039/c6py01221c	journal	January 2017
Preparation of a lignin-based vitrimer material and its potential use for recoverable adhesives Zhang, Shuai; Liu, Tuan; Hao, Cheng Green Chemistry, Vol. 20, Issue 13 https://doi.org/10.1039/c8gc01299g	journal	January 2018
Readily recyclable, high-performance thermosetting materials based on a lignin-derived spiro diacetal trigger Ma, Songqi; Wei, Jingjing; Jia, Zhen Journal of Materials Chemistry A, Vol. 7, Issue 3 https://doi.org/10.1039/c8ta07140c	journal	January 2019
Intensified ozonolysis of lignins in a spray reactor: insights into product yields and lignin structure Silverman, Julian R.; Danby, Andrew M.; Subramaniam, Bala Reaction Chemistry & Engineering, Vol. 4, Issue 8 https://doi.org/10.1039/c9re00098d	journal	January 2019
Reprocessable and degradable thermoset with high T_g cross-linked via Si–O–Ph bonds Gao, Sheng; Liu, Ying; Feng, Shengyu Journal of Materials Chemistry A, Vol. 7, Issue 29 https://doi.org/10.1039/c9ta04951g	journal	January 2019
Preparation of non-isocyanate polyurethanes from epoxy soybean oil: dual dynamic networks to realize self-healing and reprocessing under mild conditions Yang, Xinxin; Wang, Shibo; Liu, Xiuxiu Green Chemistry, Vol. 23, Issue 17 https://doi.org/10.1039/d1gc01936h	journal	January 2021
Blended vinylogous urethane/urea vitrimers derived from aromatic alcohols Haida, Philipp; Signorato, Gloria; Abetz, Volker Polymer Chemistry, Vol. 13, Issue 7 https://doi.org/10.1039/d1py01237a	journal	January 2022
Strategies for lignin depolymerization and reconstruction towards functional polymers Jiang, Lu; Wang, Chen-Gang; Chee, Pei Lin Sustainable Energy & Fuels, Vol. 7, Issue 13 https://doi.org/10.1039/d3se00173c	journal	January 2023
Preparation of lignin-based imine vitrimers and their potential application as repairable, self-cleaning, removable and degradable coatings Liu, Jian; Bernaerts, Katrien V. Journal of Materials Chemistry A, Vol. 12, Issue 5 https://doi.org/10.1039/d3ta06338k	journal	January 2024
Study on synthesis and road performance of light-colored resin modified asphalt Zhang, Zhao; Huang, Zhouyi; Zhou, Wei IOP Conference Series: Earth and Environmental Science, Vol. 770, Issue 1 https://doi.org/10.1088/1755-1315/770/1/012003	journal	May 2021
A Thermally Re-mendable Cross-Linked Polymeric Material Chen, Xiangxu; Dam, Matheus A.; Ono, Kanji Science, Vol. 295, Issue 5560, p. 1698-1702 https://doi.org/10.1126/science.1065879	journal	March 2002
Photoinduced Plasticity in Cross-Linked Polymers Scott, T. F. Science, Vol. 308, Issue 5728 https://doi.org/10.1126/science.1110505	journal	June 2005
Silica-Like Malleable Materials from Permanent Organic Networks Montarnal, D.; Capelot, M.; Tournilhac, F. Science, Vol. 334, Issue 6058 https://doi.org/10.1126/science.1212648	journal	November 2011
Lignin Valorization: Improving Lignin Processing in the Biorefinery Ragauskas, A. J.; Beckham, G. T.; Biddy, M. J. Science, Vol. 344, Issue 6185, p. 1246843-1246843 https://doi.org/10.1126/science.1246843	journal	May 2014
Polymers from Biomass: Characterization, Modification, Degradation, and Applications Adsul, Mukund; Tuli, Deepak K.; Annamalai, Pratheep K. International Journal of Polymer Science, Vol. 2016 https://doi.org/10.1155/2016/1857297	journal	January 2016
Structural Characterization of Lignin and Its Degradation Products with Spectroscopic Methods Lu, Yao; Lu, Yong-Chao; Hu, Hong-Qin Journal of Spectroscopy, Vol. 2017 https://doi.org/10.1155/2017/8951658	journal	January 2017
Study on the Preparation and Application of Lignin-Derived Polycarboxylic Acids Wang, Ruiqi; Zhou, Bing; Wang, Zichen Journal of Chemistry, Vol. 2019 https://doi.org/10.1155/2019/5493745	journal	April 2019
Depolymerization and conversion of lignin to value-added bioproducts by microbial and enzymatic catalysis Weng, Caihong; Peng, Xiaowei; Han, Yejun Biotechnology for Biofuels, Vol. 14, Issue 1 https://doi.org/10.1186/s13068-021-01934-w	journal	April 2021
Co-curing of epoxy resins with aminated lignins: insights into the role of lignin homo crosslinking during lignin amination on the elastic properties Ott, Marcus W.; Dietz, Christian; Trosien, Simon Holzforschung, Vol. 75, Issue 4 https://doi.org/10.1515/hf-2020-0060	journal	August 2020
Multifunctional Lignin-Based Composite Materials for Emerging Applications Ma, Chang; Kim, Tae-Hee; Liu, Kun Frontiers in Bioengineering and Biotechnology, Vol. 9 https://doi.org/10.3389/fbioe.2021.708976	journal	July 2021
About Making Lignin Great Again—Some Lessons From the Past Glasser, Wolfgang G. Frontiers in Chemistry, Vol. 7 https://doi.org/10.3389/fchem.2019.00565	journal	August 2019
Lignocellulosic Biomass: Understanding Recalcitrance and Predicting Hydrolysis Zoghlami, Aya; Paës, Gabriel Frontiers in Chemistry, Vol. 7 https://doi.org/10.3389/fchem.2019.00874	journal	December 2019
The Effect of Plant Source on the Properties of Lignin-Based Polyurethanes Lang, Jason M.; Shrestha, Umesh M.; Dadmun, Mark Frontiers in Energy Research, Vol. 6 https://doi.org/10.3389/fenrg.2018.00004	journal	February 2018
Epoxidation of Kraft Lignin as a Tool for Improving the Mechanical Properties of Epoxy Adhesive Gouveia, Julia R.; Garcia, Guilherme E. S.; Antonino, Leonardo Dalseno Molecules, Vol. 25, Issue 11 https://doi.org/10.3390/molecules25112513	journal	May 2020
The Impact of Vitrimers on the Industry of the Future: Chemistry, Properties and Sustainable Forward-Looking Applications Alabiso, Walter; Schlögl, Sandra Polymers, Vol. 12, Issue 8 https://doi.org/10.3390/polym12081660	journal	July 2020
Insights into the Potential of Hardwood Kraft Lignin to Be a Green Platform Material for Emergence of the Biorefinery Jardim, Juliana M.; Hart, Peter W.; Lucia, Lucian Polymers, Vol. 12, Issue 8 https://doi.org/10.3390/polym12081795	journal	August 2020
Recent Advances in Renewable Polymer Production from Lignin-Derived Aldehydes Lee, Nahyeon; Kim, Yong Tae; Lee, Jechan Polymers, Vol. 13, Issue 3 https://doi.org/10.3390/polym13030364	journal	January 2021
Preparation of Chemically Modified Lignin-Reinforced PLA Biocomposites and Their 3D Printing Performance Hong, Seo-Hwa; Park, Jin Hwan; Kim, Oh Young Polymers, Vol. 13, Issue 4 https://doi.org/10.3390/polym13040667	journal	February 2021
Boronic Acid Esters and Anhydrates as Dynamic Cross-Links in Vitrimers Gosecki, Mateusz; Gosecka, Monika Polymers, Vol. 14, Issue 4 https://doi.org/10.3390/polym14040842	journal	February 2022
Recycling of Thermoset Materials and Thermoset-Based Composites: Challenge and Opportunity Morici, Elisabetta; Dintcheva, Nadka Tz. Polymers, Vol. 14, Issue 19 https://doi.org/10.3390/polym14194153	journal	October 2022
Bio-Vitrimers for Sustainable Circular Bio-Economy Rana, Sravendra; Solanki, Manisha; Sahoo, Nanda Gopal Polymers, Vol. 14, Issue 20 https://doi.org/10.3390/polym14204338	journal	October 2022
Structural Changes of Alkali Lignin under Ozone Treatment and Effect of Ozone-Oxidized Alkali Lignin on Cellulose Digestibility Wang, Hongyuan; Zhao, Lihong; Ren, Junli Processes, Vol. 10, Issue 3 https://doi.org/10.3390/pr10030559	journal	March 2022

Similar Records

Lignin valorization reshapes sustainable biomass refining

Journal Article · 2024 · Renewable and Sustainable Energy Reviews · OSTI ID:2538169

Liu, Zhi-Hua; Liu, He; Xu, Tao; +5 more

Lignin Valorization: Improving Lignin Processing in the Biorefinery

Journal Article · 2014 · Science · OSTI ID:1154822

Ragauskas, Arthur; Beckham, Gregg; Biddy, Mary J; +13 more

Finding values in lignin: A promising yet under-utilized component of the lignocellulosic biomass

Journal Article · 2022 · Frontiers in Chemical Engineering · OSTI ID:2280424

Jassal, Vidhisha; Dou, Chang; Sun, Ning; +3 more

Title: Lignin-based vitrimers: valorization and utilization of lignin in high-value applications

Citation Formats

References (121)

Similar Records

Related Subjects