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A Novel and Formaldehyde-Free Preparation Method for Lignin Amine and Its Enhancement for Soy Protein Adhesive

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Abstract

In this work, a novel two-step process to prepare primary lignin amine was developed. The lignin used in this study was obtained from the residue of cellulosic sugar fermentation for bioethanol (referred as “lignin”). The lignin was initially oxidized through Fenton oxidation. The oxidized lignin was further converted to lignin amine by reductive amination. Ammonia was used in the second step leading to give the highly active primary lignin amine. The oxidation and reduction exhibited relatively high yields of 80.0 and 91.2 % respectively. For comparison, lignin was partially depolymerized via mild hydrogenolysis and then the partial depolymerized lignin was also converted to lignin amine using the same method. The obtained lignin amines were characterized in detail using elemental analysis, proton nuclear magnetic resonance (1H NMR), and Fourier transform infrared spectroscopy (FTIR). Further, modification of soy protein adhesive by lignin amine was exemplified in wood bonding, and the results indicated that addition of lignin amine greatly increased water resistance of soy protein adhesives.

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Acknowledgments

This work was made possible by the Northwest Advanced Renewables Alliance (NARA) funded by the Agriculture and Food Research Initiative Competitive Grant No. 2011-68005-30416 of the USDA and National Institute of Food and Agriculture and from the Sungrant/United States Department of Transportation (Contract no. T0013G-A-9). We also like to acknowledge Dr. Johnway Gao for his technical support with preparation of enzymolysis lignin.

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Authors and Affiliations

  1. Composite Materials and Engineering Center, Washington State University, PO Box 641806, Pullman, WA, 99164, USA

    Junna Xin, Pei Zhang, Michael P. Wolcott & Jinwen Zhang

  2. Nuclear Magnetic Resonance Center, Washington State University, Pullman, WA, 99164, USA

    William C. Hiscox

  3. Bioproducts, Science and Engineering Laboratory, Voiland School of Chemical Engineering and Bioengineering, Washington State University, Richland, WA, 99354, USA

    Xiao Zhang

Authors
  1. Junna Xin
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  2. Pei Zhang
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  3. Michael P. Wolcott
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  4. Jinwen Zhang
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  5. William C. Hiscox
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  6. Xiao Zhang
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Correspondence to Jinwen Zhang.

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Xin, J., Zhang, P., Wolcott, M.P. et al. A Novel and Formaldehyde-Free Preparation Method for Lignin Amine and Its Enhancement for Soy Protein Adhesive. J Polym Environ 25, 599–605 (2017). https://doi.org/10.1007/s10924-016-0844-x

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  • DOI: https://doi.org/10.1007/s10924-016-0844-x

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