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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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          The future of reversible addition fragmentation chain transfer polymerization

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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
            6026785
            10.1021/acscentsci.8b00140
            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.

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            Research Article
            Custom metadata
            oc8b00140
            oc-2018-001404

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