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

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 themore » practical significance of our biomass-derived materials.« less

Authors:
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
Publication Date:
Research Org.:
Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation (CCEI); Univ. of Delaware, Newark, DE (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF); National Inst. of Health (NIH) (United States)
OSTI Identifier:
1437200
Alternate Identifier(s):
OSTI ID: 1498666; OSTI ID: 1508817
Grant/Contract Number:  
SC0001004; CHE-1507010; 1 P30 GM110758-01
Resource Type:
Published Article
Journal Name:
ACS Central Science
Additional Journal Information:
Journal Name: ACS Central Science Journal Volume: 4 Journal Issue: 6; Journal ID: ISSN 2374-7943
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 09 BIOMASS FUELS

Citation Formats

Wang, Shu, Shuai, Li, Saha, Basudeb, Vlachos, Dionisios G., and Epps, III, Thomas H. From Tree to Tape: Direct Synthesis of Pressure Sensitive Adhesives from Depolymerized Raw Lignocellulosic Biomass. United States: N. p., 2018. Web. https://doi.org/10.1021/acscentsci.8b00140.
Wang, Shu, Shuai, Li, Saha, Basudeb, Vlachos, Dionisios G., & Epps, III, Thomas H. From Tree to Tape: Direct Synthesis of Pressure Sensitive Adhesives from Depolymerized Raw Lignocellulosic Biomass. United States. https://doi.org/10.1021/acscentsci.8b00140
Wang, Shu, Shuai, Li, Saha, Basudeb, Vlachos, Dionisios G., and Epps, III, Thomas H. Tue . "From Tree to Tape: Direct Synthesis of Pressure Sensitive Adhesives from Depolymerized Raw Lignocellulosic Biomass". United States. https://doi.org/10.1021/acscentsci.8b00140.
@article{osti_1437200,
title = {From Tree to Tape: Direct Synthesis of Pressure Sensitive Adhesives from Depolymerized Raw Lignocellulosic Biomass},
author = {Wang, Shu and Shuai, Li and Saha, Basudeb and Vlachos, Dionisios G. and Epps, III, Thomas H.},
abstractNote = {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.},
doi = {10.1021/acscentsci.8b00140},
journal = {ACS Central Science},
number = 6,
volume = 4,
place = {United States},
year = {2018},
month = {5}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1021/acscentsci.8b00140

Citation Metrics:
Cited by: 12 works
Citation information provided by
Web of Science

Figures / Tables:

Scheme 1 Scheme 1: Process from Raw Biomass to PSAs (4-Propylsyringol, R = OCH3; 4-Propylguaiacol, R = H)

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Works referencing / citing this record:

First insights of SHVO catalyst activity for monomeric phenol production from olive pomace
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  • Cequier, Enrique; Balcells, Mercè; Canela‐Garayoa, Ramon
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Extraction and characterization of lignin from olive pomace: a comparison study among ionic liquid, sulfuric acid, and alkaline treatments
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  • Cequier, Enrique; Aguilera, Johanna; Balcells, Mercè
  • Biomass Conversion and Biorefinery, Vol. 9, Issue 2
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Lignin from second-generation biorefinery for pressure-sensitive adhesive tapes
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Differences in S/G ratio in natural poplar variants do not predict catalytic depolymerization monomer yields
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  • Liu, Xue; Li, Helong; Xiao, Ling-Ping
  • Green Chemistry, Vol. 21, Issue 6
  • DOI: 10.1039/c8gc03511c

Recent advances in RAFT polymerization of monomers derived from renewable resources
journal, January 2020


Lignin Biopolymers in the Age of Controlled Polymerization
journal, July 2019

  • Ganewatta, Mitra S.; Lokupitiya, Hasala N.; Tang, Chuanbing
  • Polymers, Vol. 11, Issue 7
  • DOI: 10.3390/polym11071176

Synthesis of Lignin-Based Polyacid Catalyst and Its Utilization to Improve Water Resistance of Urea–formaldehyde Resins
journal, January 2020


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