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Crosslinking Mechanism of Soy Protein-based Adhesives based on Glyoxal and a Compound of Protein Model

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Abstract

The crosslinking mechanism of glyoxal and asparagine was analyzed, and the relationship between the mechanism and practical performances of soy protein-based adhesives was also discussed. It is shown that when pH=1 and 3, glyoxal reacted with asparagine in the form of major cyclic ether compounds. When pH =5, glyoxal reacted with asparagine in two structural forms of sodium glycollate and cyclic ether compounds. However, amidogens of asparagine were easy to develop protonation under acid conditions. Supplemented by the instability of cyclic ether compounds, the reaction activity and reaction degree between glyoxal and asparagine were relatively small. Under alkaline conditions, glyoxal mainly reacted with asparagine in the form of sodium glycollate. With the increase of pH, the polycondensation was more sufficient and the produced polycondensation products were more stable. The reaction mechanism between glyoxal and asparagine had strong correspondence to the practical performances of the adhesives. Glyoxal solution could develop crosslinking reactions with soy protein under both acid and alkaline conditions. Bonding strength and water resistance of the prepared soy protein-based adhesives were increased significantly. When pH>7, glyoxal had relatively high reaction activity and reaction intensity with soy protein, and the prepared adhesives had high crosslinking density and cohesion strength, showing relatively high bonding strength, water resistance and thermal stability.

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Acknowledgements

The authors thank the anonymous reviewers for their invaluable comments and suggestions to improve the quality of the paper.

Author information

Authors and Affiliations

  1. Yunnan Provincial Key Laboratory of Wood Adhesives and Glued Products, Southwest Forestry University, Kunming, 650224, China

    Long Cao  (曹龙) & Xuedong Xi

  2. College of Civil Engineering, Kaili University, Qiandongnan, Kaili, 556011, China

    Jiankun Liang

  3. Zhazuo State-owned Forest Farm, Guiyang, 550299, China

    Qiaoyan Zhang

  4. College of Forestry, Guizhou University, Guiyang, 550025, China

    Zhigang Wu  (吴志刚)

  5. School of Chemistry Materials Engineering, Zhejiang A&F University, Hangzhou, 311300, China

    Hong Lei  (雷洪)

Authors
  1. Long Cao  (曹龙)
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  2. Jiankun Liang
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  3. Qiaoyan Zhang
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  4. Xuedong Xi
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  5. Zhigang Wu  (吴志刚)
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  6. Hong Lei  (雷洪)
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Corresponding authors

Correspondence to Zhigang Wu  (吴志刚) or Hong Lei  (雷洪).

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Conflict of interest

All authors declare that there are no competing interests.

Funded by the National Natural Science Foundation of China (No.32160348), the Department Program of Guizhou Province (No. ZK[2021]162), the Guizhou Province Science and Technology Plan Project (No.[2020]1Y128), and the Forestry Department Foundation of Guizhou Province of China (Nos.J[2022]21 and [2020]C14)

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Cao, L., Liang, J., Zhang, Q. et al. Crosslinking Mechanism of Soy Protein-based Adhesives based on Glyoxal and a Compound of Protein Model. J. Wuhan Univ. Technol.-Mat. Sci. Edit. 38, 942–950 (2023). https://doi.org/10.1007/s11595-023-2781-6

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  • DOI: https://doi.org/10.1007/s11595-023-2781-6

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