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

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          Abstract

          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.

          Abstract

          We demonstrated the successful incorporation of materials obtained directly from raw biomass deconstruction in the development of nanostructured pressure sensitive adhesives for use in tapes.

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          Most cited references 44

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          Chemical modification of lignins: Towards biobased polymers

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            Reductive lignocellulose fractionation into soluble lignin-derived phenolic monomers and dimers and processable carbohydrate pulps

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              Formaldehyde stabilization facilitates lignin monomer production during biomass depolymerization

              Practical, high-yield lignin depolymerization methods could greatly increase biorefinery productivity and profitability. However, development of these methods is limited by the presence of interunit carbon-carbon bonds within native lignin, and further by formation of such linkages during lignin extraction. We report that adding formaldehyde during biomass pretreatment produces a soluble lignin fraction that can be converted to guaiacyl and syringyl monomers at near theoretical yields during subsequent hydrogenolysis (47 mole % of Klason lignin for beech and 78 mole % for a high-syringyl transgenic poplar). These yields were three to seven times those obtained without formaldehyde, which prevented lignin condensation by forming 1,3-dioxane structures with lignin side-chain hydroxyl groups. By depolymerizing cellulose, hemicelluloses, and lignin separately, monomer yields were between 76 and 90 mole % for these three major biomass fractions.
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                Author and article information

                Affiliations
                []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
                [§ ]Department of Materials Science & Engineering, University of Delaware , Newark, Delaware 19716, United States
                Author notes
                Journal
                ACS Cent Sci
                ACS Cent Sci
                oc
                acscii
                ACS Central Science
                American Chemical Society
                2374-7943
                2374-7951
                15 May 2018
                27 June 2018
                : 4
                : 6
                : 701-708
                10.1021/acscentsci.8b00140
                6026785
                Copyright © 2018 American Chemical Society

                This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.

                Categories
                Research Article
                Custom metadata
                oc8b00140
                oc-2018-001404

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