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Title: From Tree to Tape: Direct Synthesis of Pressure Sensitive Adhesives from Depolymerized Raw Lignocellulosic Biomass

Journal Article · · ACS Central Science
ORCiD logo [1];  [2];  [2]; ORCiD logo [3]; ORCiD logo [4]
  1. Department of Chemical & Biomolecular Engineering, University of Delaware, Newark, Delaware 19716, United States
  2. Center for Energy Innovation, University of Delaware, Newark, Delaware 19716, United States
  3. Department of Chemical & Biomolecular Engineering, University of Delaware, Newark, Delaware 19716, United States, Center for Energy Innovation, University of Delaware, Newark, Delaware 19716, United States
  4. Department of Chemical & Biomolecular Engineering, University of Delaware, Newark, Delaware 19716, United States, Department of Materials Science & Engineering, University of Delaware, Newark, Delaware 19716, United States

We report a new and robust strategy toward the development of high-performance pressure sensitive adhesives (PSAs) from chemicals directly obtained from raw biomass deconstruction. A particularly unique and translatable aspect of this work was the use of a monomer obtained from real biomass, as opposed to a model compound or lignin-mimic, to generate well-defined and nanostructure-forming polymers. Herein, poplar wood depolymerization followed by minimal purification steps (filtration and extraction) produced two aromatic compounds, 4-propylsyringol and 4-propylguaiacol, with high purity and yield. Efficient functionalization of those aromatic compounds with either acrylate or methacrylate groups generated monomers that could be easily polymerized by a scalable reversible addition–fragmentation chain-transfer (RAFT) process to yield polymeric materials with high glass transition temperatures and robust thermal stabilities, especially relative to other potentially biobased alternatives. These lignin-derived compounds were used as a major component in low-dispersity triblock polymers composed of 4-propylsyringyl acrylate and n-butyl acrylate (also can be biobased). The resulting PSAs exhibited excellent adhesion to stainless steel without the addition of any tackifier or plasticizer. The 180° peel forces were up to 4 N cm–1, and tack forces were up to 2.5 N cm–1, competitive with commercial Fisherbrand labeling tape and Scotch Magic tape, demonstrating the practical significance of our biomass-derived materials.

Research Organization:
Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation (CCEI); Univ. of Delaware, Newark, DE (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF); National Inst. of Health (NIH) (United States)
Grant/Contract Number:
SC0001004; CHE-1507010; 1 P30 GM110758-01
OSTI ID:
1437200
Alternate ID(s):
OSTI ID: 1498666; OSTI ID: 1508817
Journal Information:
ACS Central Science, Journal Name: ACS Central Science Vol. 4 Journal Issue: 6; ISSN 2374-7943
Publisher:
American Chemical SocietyCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 82 works
Citation information provided by
Web of Science

References (43)

Molecular parameters and their relation to the adhesive performance of acrylic pressure-sensitive adhesives journal January 2001
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
Lignin-Based Bio-Oil Mimic as Biobased Resin for Composite Applications journal February 2013
Lignin Depolymerization into Aromatic Monomers over Solid Acid Catalysts journal November 2014
Pressure-Sensitive Adhesives: An Introductory Course journal June 2003
Bright Side of Lignin Depolymerization: Toward New Platform Chemicals journal January 2018
Thermochemical conversion of lignin to functional materials: a review and future directions journal January 2015
High-Performance Pressure-Sensitive Adhesives from Renewable Triblock Copolymers journal July 2015
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
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
From models to lignin: Transition metal catalysis for selective bond cleavage reactions journal January 2016
Reductive lignocellulose fractionation into soluble lignin-derived phenolic monomers and dimers and processable carbohydrate pulps journal January 2015
Synthesis of poly(methyl methacrylate)-b-poly(n-butyl acrylate)-b-poly(methyl methacrylate) triblocks and their potential as thermoplastic elastomers journal March 2000
Biochemical transformation of lignin for deriving valued commodities from lignocellulose journal June 2017
Acrylic Triblock Copolymers Incorporating Isosorbide for Pressure Sensitive Adhesives journal May 2016
Softwood Lignin-Based Methacrylate Polymers with Tunable Thermal and Viscoelastic Properties journal February 2016
Model hydrocarbon polymers: rheological properties of linear polyisoprenes and hydrogenated polyisoprenes journal December 1984
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
A Facile Method for Generating Designer Block Copolymers from Functionalized Lignin Model Compounds journal January 2014
Effect of Methoxy Substituent Position on Thermal Properties and Solvent Resistance of Lignin-Inspired Poly(dimethoxyphenyl methacrylate)s journal July 2017
Biobased Epoxy Resins from Deconstructed Native Softwood Lignin journal July 2017
The effect of molecular weight and temperature on tack properties of model polyisobutylenes journal August 2004
Selective production of 4-ethylphenolics from lignin via mild hydrogenolysis journal August 2012
Hydrogenolysis of lignosulfonate into phenols over heterogeneous nickel catalysts journal April 2012
Turning renewable resources into value-added polymer: development of lignin-based thermoplastic journal January 2012
Syringyl Methacrylate, a Hardwood Lignin-Based Monomer for High- T g Polymeric Materials journal April 2016
Tack and viscoelastic properties of an acrylic block copolymer/tackifier system journal December 2009
Fast pyrolysis of Kraft lignin—Vapor cracking over various fixed-bed catalysts journal March 2013
Biphasic extraction of mechanocatalytically-depolymerized lignin from water-soluble wood and its catalytic downstream processing journal January 2017
Determination of Solvent–Polymer and Polymer–Polymer Flory–Huggins Interaction Parameters for Poly(3-hexylthiophene) via Solvent Vapor Swelling journal August 2013
Chemical modification of lignins: Towards biobased polymers journal July 2014
Vanillin-based resin for use in composite applications journal January 2012
Catalytic Biorefining of Plant Biomass to Non-Pyrolytic Lignin Bio-Oil and Carbohydrates through Hydrogen Transfer Reactions journal June 2014
Chemistry of lignin-based materials journal September 2013
Formaldehyde stabilization facilitates lignin monomer production during biomass depolymerization journal October 2016
Tunable Thermosetting Epoxies Based on Fractionated and Well-Characterized Lignins journal March 2018
Pressure-Sensitive Adhesives from Renewable Triblock Copolymers journal January 2011
Lignin Valorization: Two Hybrid Biochemical Routes for the Conversion of Polymeric Lignin into Value-added Chemicals journal August 2017
Towards high-yield lignin monomer production journal January 2017
The future of reversible addition fragmentation chain transfer polymerization journal September 2008

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