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

Journal Article · · ACS Macro Letters

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.

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
Citation Metrics:
Cited by: 37 works
Citation information provided by
Web of Science

References (35)

Opportunities and challenges in biological lignin valorization journal December 2016
Lignin Valorization: Improving Lignin Processing in the Biorefinery journal May 2014
Lignin and Lignans book August 2010
Complete lignocellulose conversion with integrated catalyst recycling yielding valuable aromatics and fuels journal January 2018
Bright Side of Lignin Depolymerization: Toward New Platform Chemicals journal January 2018
Lignin Depolymerization and Conversion A Review of Thermochemical Methods journal November 2010
Variation in Lignin Content and Composition (Mechanisms of Control and Implications for the Genetic Improvement of Plants) journal January 1996
Lignin Biosynthesis and Structure journal May 2010
New insights into the structure and composition of technical lignins: a comparative characterisation study journal January 2016
Polyphenolic Substance of Mytilus edulis: Novel Adhesive Containing L-Dopa and Hydroxyproline journal May 1981
Mussel-Inspired Surface Chemistry for Multifunctional Coatings journal October 2007
Catechol-Based Biomimetic Functional Materials journal November 2012
Toughening elastomers using mussel-inspired iron-catechol complexes journal October 2017
Linking Hydrophilic Macromolecules to Monodisperse Magnetite (Fe 3 O 4 ) Nanoparticles via Trichloro- s -triazine journal November 2006
Visible absorption spectra of metal–catecholate and metal–tironate complexes journal January 2004
pH-induced metal-ligand cross-links inspired by mussel yield self-healing polymer networks with near-covalent elastic moduli journal January 2011
Quantum Chemical Determination of Young's Modulus of Lignin. Calculations on a β−O-4‘ Model Compound journal November 2007
Self-healing polymeric materials journal January 2013
Self-healing and thermoreversible rubber from supramolecular assembly journal February 2008
Self-Repairing Oxetane-Substituted Chitosan Polyurethane Networks journal March 2009
A Healable Supramolecular Polymer Blend Based on Aromatic π−π Stacking and Hydrogen-Bonding Interactions journal September 2010
Optically healable supramolecular polymers journal April 2011
A highly stretchable autonomous self-healing elastomer journal April 2016
Self-Healing of Poly(Ethylene-co-Methacrylic Acid) Copolymers Following Projectile Puncture journal June 2007
A self-healable and highly stretchable supercapacitor based on a dual crosslinked polyelectrolyte journal December 2015
Self-Healing, Expansion-Contraction, and Shape-Memory Properties of a Preorganized Supramolecular Hydrogel through Host-Guest Interactions journal June 2015
Multiphase design of autonomic self-healing thermoplastic elastomers journal April 2012
Multivalent hydrogen bonding block copolymers self-assemble into strong and tough self-healing materials journal January 2014
Self-Healing Multiphase Polymers via Dynamic Metal–Ligand Interactions journal November 2014
Glycidyl Ether Reactions with Alcohols, Phenols, Carboxylic Acids, and Acid Anhydrides journal January 1956
Double-Network Hydrogels with Extremely High Mechanical Strength journal July 2003
Highly stretchable and tough hydrogels journal September 2012
Physical hydrogels composed of polyampholytes demonstrate high toughness and viscoelasticity journal July 2013
Multi-scale multi-mechanism design of tough hydrogels: building dissipation into stretchy networks journal January 2014
Intrinsically stretchable and healable semiconducting polymer for organic transistors journal November 2016

Cited By (2)

Synthesis of Lignin-Based Polyacid Catalyst and Its Utilization to Improve Water Resistance of Urea–formaldehyde Resins journal January 2020
A Cast Net Thrown onto an Interface: Wrapping 3D Objects with an Interfacially Jammed Amphiphilic Sheet journal April 2020

Figures / Tables (6)