Rigid Oligomer from Lignin in Designing of Tough, Self-Healing Elastomers

Cui, Mengmeng; Nguyen, Ngoc A.; Bonnesen, Peter V.; Uhrig, David; Keum, Jong K.; Naskar, Amit K.

doi:10.1021/acsmacrolett.8b00600

Title: Rigid Oligomer from Lignin in Designing of Tough, Self-Healing Elastomers

Journal Article · 16 October 2018 · ACS Macro Letters

DOI: https://doi.org/10.1021/acsmacrolett.8b00600 · OSTI ID:1483177

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Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

Here, converting lignin into well-defined compounds is often challenged by structural complexation and inorganic contamination induced by the pulping process. In this report, instead of breaking down lignin into small molecules, we extracted a uniform and rigid oligomer from the lignin waste stream. The multifunctional polyphenol oligomer containing carboxylic acid, alcohol, and phenol groups is highly reactive and brings stiffness into the material matrix. Tough and self-healing elastomers are economically prepared from this oligomer by a reaction with epoxy-terminated polyethylene glycol, without needing any solvent. Specifically, the polyaromatic backbone’s rigidity enhances the elastomer’s toughness, and the multiple polar substituents form a network of hydrogen bonding that heals the elastomer. Many other applications, including adhesives, hydrogels, coating, and metal scavengers, are envisioned based on this oligomer’s unique properties.

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Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1483177

Journal Information:: ACS Macro Letters, Vol. 7, Issue 11; ISSN 2161-1653

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 44 works

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References (34)

Opportunities and challenges in biological lignin valorization Beckham, Gregg T.; Johnson, Christopher W.; Karp, Eric M. Current Opinion in Biotechnology, Vol. 42 https://doi.org/10.1016/j.copbio.2016.02.030	journal	December 2016
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
Lignin and Lignans Heitner, Cyril; Dimmel, Don; Schmidt, John https://doi.org/10.1201/EBK1574444865	book	August 2010
Complete lignocellulose conversion with integrated catalyst recycling yielding valuable aromatics and fuels Sun, Zhuohua; Bottari, Giovanni; Afanasenko, Anastasiia Nature Catalysis, Vol. 1, Issue 1 https://doi.org/10.1038/s41929-017-0007-z	journal	January 2018
Bright Side of Lignin Depolymerization: Toward New Platform Chemicals Sun, Zhuohua; Fridrich, Bálint; de Santi, Alessandra Chemical Reviews, Vol. 118, Issue 2 https://doi.org/10.1021/acs.chemrev.7b00588	journal	January 2018
Lignin Depolymerization and Conversion A Review of Thermochemical Methods Pandey, M. P.; Kim, C. S. Chemical Engineering & Technology, Vol. 34, Issue 1, p. 29-41 https://doi.org/10.1002/ceat.201000270	journal	November 2010
Variation in Lignin Content and Composition (Mechanisms of Control and Implications for the Genetic Improvement of Plants) Campbell, M. M.; Sederoff, R. R. Plant Physiology, Vol. 110, Issue 1 https://doi.org/10.1104/pp.110.1.3	journal	January 1996
Lignin Biosynthesis and Structure Vanholme, R.; Demedts, B.; Morreel, K. Plant Physiology, Vol. 153, Issue 3, p. 895-905 https://doi.org/10.1104/pp.110.155119	journal	May 2010
New insights into the structure and composition of technical lignins: a comparative characterisation study Constant, Sandra; Wienk, Hans L. J.; Frissen, Augustinus E. Green Chemistry, Vol. 18, Issue 9 https://doi.org/10.1039/C5GC03043A	journal	January 2016
Polyphenolic Substance of Mytilus edulis: Novel Adhesive Containing L-Dopa and Hydroxyproline Waite, J. H.; Tanzer, M. L. Science, Vol. 212, Issue 4498 https://doi.org/10.1126/science.212.4498.1038	journal	May 1981
Mussel-Inspired Surface Chemistry for Multifunctional Coatings Lee, H.; Dellatore, S. M.; Miller, W. M. Science, Vol. 318, Issue 5849 https://doi.org/10.1126/science.1147241	journal	October 2007
Catechol-Based Biomimetic Functional Materials Sedó, Josep; Saiz-Poseu, Javier; Busqué, Felix Advanced Materials, Vol. 25, Issue 5 https://doi.org/10.1002/adma.201202343	journal	November 2012
Toughening elastomers using mussel-inspired iron-catechol complexes Filippidi, Emmanouela; Cristiani, Thomas R.; Eisenbach, Claus D. Science, Vol. 358, Issue 6362 https://doi.org/10.1126/science.aao0350	journal	October 2017
Linking Hydrophilic Macromolecules to Monodisperse Magnetite (Fe ₃ O ₄ ) Nanoparticles via Trichloro- s -triazine Xie, Jin; Xu, Chenjie; Xu, Zhichuan Chemistry of Materials, Vol. 18, Issue 23 https://doi.org/10.1021/cm061793c	journal	November 2006
pH-induced metal-ligand cross-links inspired by mussel yield self-healing polymer networks with near-covalent elastic moduli Holten-Andersen, N.; Harrington, M. J.; Birkedal, H. Proceedings of the National Academy of Sciences, Vol. 108, Issue 7, p. 2651-2655 https://doi.org/10.1073/pnas.1015862108	journal	January 2011
Quantum Chemical Determination of Young's Modulus of Lignin. Calculations on a β−O-4‘ Model Compound Elder, Thomas Biomacromolecules, Vol. 8, Issue 11 https://doi.org/10.1021/bm700663y	journal	November 2007
Self-healing polymeric materials Yang, Ying; Urban, Marek W. Chemical Society Reviews, Vol. 42, Issue 17 https://doi.org/10.1039/c3cs60109a	journal	January 2013
Self-healing and thermoreversible rubber from supramolecular assembly Cordier, Philippe; Tournilhac, François; Soulié-Ziakovic, Corinne Nature, Vol. 451, Issue 7181, p. 977-980 https://doi.org/10.1038/nature06669	journal	February 2008
Self-Repairing Oxetane-Substituted Chitosan Polyurethane Networks Ghosh, B.; Urban, M. W. Science, Vol. 323, Issue 5920 https://doi.org/10.1126/science.1167391	journal	March 2009
A Healable Supramolecular Polymer Blend Based on Aromatic π−π Stacking and Hydrogen-Bonding Interactions Burattini, Stefano; Greenland, Barnaby W.; Merino, Daniel Hermida Journal of the American Chemical Society, Vol. 132, Issue 34 https://doi.org/10.1021/ja104446r	journal	September 2010
Optically healable supramolecular polymers Burnworth, Mark; Tang, Liming; Kumpfer, Justin R. Nature, Vol. 472, Issue 7343, p. 334-337 https://doi.org/10.1038/nature09963	journal	April 2011
A highly stretchable autonomous self-healing elastomer Li, Cheng-Hui; Wang, Chao; Keplinger, Christoph Nature Chemistry, Vol. 8, Issue 6 https://doi.org/10.1038/nchem.2492	journal	April 2016
Self-Healing of Poly(Ethylene-co-Methacrylic Acid) Copolymers Following Projectile Puncture Kalista, Stephen J.; Ward, Thomas C.; Oyetunji, Zainab Mechanics of Advanced Materials and Structures, Vol. 14, Issue 5 https://doi.org/10.1080/15376490701298819	journal	June 2007
A self-healable and highly stretchable supercapacitor based on a dual crosslinked polyelectrolyte Huang, Yan; Zhong, Ming; Huang, Yang Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms10310	journal	December 2015
Self-Healing, Expansion-Contraction, and Shape-Memory Properties of a Preorganized Supramolecular Hydrogel through Host-Guest Interactions Miyamae, Kohei; Nakahata, Masaki; Takashima, Yoshinori Angewandte Chemie International Edition, Vol. 54, Issue 31 https://doi.org/10.1002/anie.201502957	journal	June 2015
Multiphase design of autonomic self-healing thermoplastic elastomers Chen, Yulin; Kushner, Aaron M.; Williams, Gregory A. Nature Chemistry, Vol. 4, Issue 6 https://doi.org/10.1038/nchem.1314	journal	April 2012
Multivalent hydrogen bonding block copolymers self-assemble into strong and tough self-healing materials Chen, Yulin; Guan, Zhibin Chem. Commun., Vol. 50, Issue 74 https://doi.org/10.1039/C4CC03168G	journal	January 2014
Self-Healing Multiphase Polymers via Dynamic Metal–Ligand Interactions Mozhdehi, Davoud; Ayala, Sergio; Cromwell, Olivia R. Journal of the American Chemical Society, Vol. 136, Issue 46 https://doi.org/10.1021/ja5097094	journal	November 2014
Glycidyl Ether Reactions with Alcohols, Phenols, Carboxylic Acids, and Acid Anhydrides Shechter, Leon; Wynstra, John Industrial & Engineering Chemistry, Vol. 48, Issue 1 https://doi.org/10.1021/ie50553a028	journal	January 1956
Double-Network Hydrogels with Extremely High Mechanical Strength Gong, J. P.; Katsuyama, Y.; Kurokawa, T. Advanced Materials, Vol. 15, Issue 14 https://doi.org/10.1002/adma.200304907	journal	July 2003
Highly stretchable and tough hydrogels Sun, Jeong-Yun; Zhao, Xuanhe; Illeperuma, Widusha R. K. Nature, Vol. 489, Issue 7414 https://doi.org/10.1038/nature11409	journal	September 2012
Physical hydrogels composed of polyampholytes demonstrate high toughness and viscoelasticity Sun, Tao Lin; Kurokawa, Takayuki; Kuroda, Shinya Nature Materials, Vol. 12, Issue 10 https://doi.org/10.1038/nmat3713	journal	July 2013
Multi-scale multi-mechanism design of tough hydrogels: building dissipation into stretchy networks Zhao, Xuanhe Soft Matter, Vol. 10, Issue 5 https://doi.org/10.1039/C3SM52272E	journal	January 2014
Intrinsically stretchable and healable semiconducting polymer for organic transistors Oh, Jin Young; Rondeau-Gagné, Simon; Chiu, Yu-Cheng Nature, Vol. 539, Issue 7629 https://doi.org/10.1038/nature20102	journal	November 2016

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