Skip to main content
SpringerLink
Log in

The Crosslinking Mechanism of Camellia Oleifera Protein Adhesive with Amine Resins by 13C-NMR and ESI-MS

  • Biomaterials
  • Published:
Journal of Wuhan University of Technology-Mater. Sci. Ed. Aims and scope Submit manuscript

Abstract

A new protein wood adhesive was studied with Camellia oleifera protein. Formaldehyde and N-(2)-L-Ala-L-Gln (LAG) were used as the model compounds of amino resins and Camellia oleifera protein, aiming to provide scientific foundations for the improvement and applications of Camellia oleifera protein adhesive by the reaction of model compounds. The experimental results demonstrate that, under alkaline conditions, formaldehyde is easier to react with Camellia oleifera protein by quicker reaction and lower curing temperature. Under acid conditions, amino hydroxymethylated structure of aliphatic series from LAG is difficult to form stable reactive intermediates and further polycondensation. Hydroxymethylation of end acylamino and peptide bond amino from LAG is relatively weak. Under alkaline conditions, the free aliphatic amino and acylamino of LAG both can make hydroxymethylation reaction with formaldehyde. In the polycondensation, hydroxymethyl amide is the initial structure and the reactive intermediate is produced by E1cb reaction of hydroxymethyl amide. Methylene bridge bonds and methylene ether bonds are structures of the polycondensation products, which are competing reactions. The former is mainly formed by the reaction between alkaline reactive intermediate and amino of aliphatic series, and the latter is produced by the reaction of reactive intermediate and amino of hydroxymethyl aliphatic series with hydroxymethyl amide.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

References

  1. Zhang S, Li X. Hypoglycemic Activity in vitro of Polysaccharides from Camellia Oleifera Abel. Seed Cake[J]. Int. J. Biol. Macromol., 2018, 115: 811–819

    Article  CAS  Google Scholar 

  2. Di T, Yang S, Du F, et al. Cytotoxic and Hypoglycemic Activity of Triterpenoid Saponins from Camellia oleifera Abel, Seed Pomace[J]. Molecules, 2017, 22(10): 1 562

    Article  Google Scholar 

  3. Chen S, Liang J, Zhang B, et al., Study on Camellia Oleifera Protein based Wood Adhesive by Epoxy Resin and Its Crosslinking Mechanism[J]. Journal of Wuhan University of Technology-Mater. Sci. Ed., 2021, 36(4): 607–613

    Article  CAS  Google Scholar 

  4. Zong J, Wang R, Bao G, et al. Novel Triterpenoid Saponins from Residual Seed Cake of Camellia Oleifera Abel. Show Anti-proliferative Activity Against Tumor Cells[J]. Fitoterapia, 2015, 104: 7–13

    Article  CAS  Google Scholar 

  5. Zhou H, Wang C, Ye J, et al. New Triterpene Saponins from the Seed Cake of Camellia Oleifera and their Cytotoxic Activity[J]. Phytochem. Lett., 2014, 8: 46–51

    Article  Google Scholar 

  6. Igwilo Christopher Nnaemeka, Egbuna Samuel O, Onoh Maxwell I, et al., Optimization and Kinetic Studies for Enzymatic Hydrolysis and Fermentation of Colocynthis Vulgaris Shrad Seeds Shell for Bioethanol Production[J]. Journal of Bioresources and Bioproducts, 2021, 6(1): 45–64

    Article  Google Scholar 

  7. Chen N, Zheng P, Zeng Q, et al., Characterization and Performance of Soy-based Adhesives Cured with Epoxy Resin[J]. Polymers, 2017, 9(10): 514

    Article  Google Scholar 

  8. Zhang A Y, Mechanical and Microscopic Analysis of Epoxy Resin Toughened Metakaolin-based Geopolymers[J]. Journal of Wuhan University of Technology-Mater. Sci. Ed., 2020, 35(2): 431–434

    Article  CAS  Google Scholar 

  9. Li J, Luo J, Li X, et al. Soybean Meal-based Wood Adhesive Enhanced by Ethylene Glycol Diglycidyl Ether and Diethylenetriamine[J]. Ind. Crop. Prod., 2015, 74: 613–618

    Article  CAS  Google Scholar 

  10. Xu F, Dong Y, Zhang W, et al. Preparation of Cross-Linked Soy Protein Isolate-Based Environmentally-Friendly Films Enhanced by PTGE and PAM[J]. Ind. Crop. Prod., 2015, 67: 375–40

    Article  Google Scholar 

  11. Wu Z, Lei H, Cao M, et al., Soy Based Adhesive Cross Linked by Melamine Glyoxal and Epoxy Resin[J]. J. Adhes. Sci. Technol., 2016, 30(19): 2 120–2 129

    Article  CAS  Google Scholar 

  12. Tang W, Xu Y, Zhao H, et al., Synthesis and Characterization of Catechol-based Polysaccharide Crosslinking Agent and Its Effect on the Properties of Soybean Protein Adhesive[J]. Journal of Forestry Engineering, 2022, 7(3): 136–143

    Google Scholar 

  13. Ma Z B, Chang S, Li M, et al., Effect of E-44 Epoxy Resin and Pyrolysis Temperature on the Adhesion Strength of SiBCN Ceramic[J]. Journal of Wuhan University of Technology-Mater. Sci. Ed., 2020, 35(1): 81–86

    Article  CAS  Google Scholar 

  14. Jin C, Zhang S, Pang J, et al. Plywood with Soy Protein-Acrylate Hybrid Adhesive[J]. Advanced Materials Research, 2014, 884–885: 108–111

    Article  Google Scholar 

  15. Li H, Liang Y, Li P, et al. Conversion of Biomass Lignin to High-value Polyurethane: A Review[J]. Journal of Bioresources and Bioproducts, 5(3): 163–179

  16. Frihart C, Satori H, Soy Flour Dispersibility and Performance as Wood Adhesive[J]. J. Adhes. Sci. Technol., 2013, 27(18–19): 2 043–2 052

    Article  CAS  Google Scholar 

  17. Xu Y, Liu L, Structural and Functional Properties of Soy Protein Isolates Modified by Soy Soluble Polysaccharides[J]. J. Agr. Food Chem., 2016, 64(38): 7 275–7 284

    Article  CAS  Google Scholar 

  18. Zhang J, Tian Y, Cui Y, et al. Key Intermediates in Nitrogen Transformation During Microwave Pyrolysis of Sewage Sludge: A Protein Model Compound Study[J]. Bioresource Technol., 2013, 132: 57–63

    Article  CAS  Google Scholar 

  19. Lei H, Wu Z, Cao M, et al., Study on the Soy Protein-Based Wood Adhesive Modified by Hydroxymethyl Phenol[J]. Polymers, 2016, 8(7): 256–265

    Article  Google Scholar 

  20. Gan W, Liu J, Zhang J, et al., Research Progress on Utilizing Liquefaction of Lignin to Modify Phenolic Resin[J]. Journal of Forestry Engineering, 2022, 7(3): 11–19

    Google Scholar 

  21. Pizzi A, Recent Developments in Eco-efficent Bio-based Adhesives for Wood Bonding[J]. Opportunities and Issues, 2006, 20(8): 829–846

    CAS  Google Scholar 

  22. Liang J, Li Q, Wu Z, et al., Competitive Polycondensation of Model Compound Melamine-Urea-Formaldehyed (MUF) Resin System by 13C NMR[J]. Journal of Bioresources and Bioproducts, 2020, 5(1): 60–66

    Article  Google Scholar 

  23. Qu P, Huang H, Wu G, et al., Hydrolyzed Soy Protein Isolates Modified Urea Formaldehyde Resins as Adhesives and Its Biodegradability[J]. J. Adhes. Sci. Technol., 2015, 29(21): 2 381–2 398

    Article  CAS  Google Scholar 

  24. Zhang N, Li Z, Xiao Y, et al., Lignin-based Phenolic Resin Modified with Whisker Silicon and Its Application[J]. Journal of Bioresources and Bioproducts, 2020, 5(1): 67–77

    Article  Google Scholar 

  25. Qi G, Li N, Wang D, et al. Physicochemical Properties of Soy Protein Adhesives Modified by 2-Octen-1-Ylsuccinic Anhydride[J]. Ind. Crop. Prod., 2013, 46: 165–172

    Article  CAS  Google Scholar 

  26. Zhang S, Dong L, Pang J, et al. The Research of Modified-Soy-Protein-Acrylate Hybrid Emulsion[J]. Advanced Materials Research, 2010, 113–116: 1 818–1 823

    Google Scholar 

  27. Zheng P, Li Y, Li F, et al. Development of Defatted Soy Flour-based Adhesives by Acid Hydrolysis of Carbonhydrates[J]. Polymers, 2017, 9: 153

    Article  Google Scholar 

  28. Zhang X, Liu Z, Zhang Y, et al. Study on Synthesis of Epoxy Quercetin and Its Effect on Soy Protein Adhesives’ Properties[J]. Journal of Forestry Engineering, 2022, 7(5): 87–92

    Google Scholar 

  29. Li J, Luo J, Li X, et al. Soybean Meal-based Wood Adhesive Enhanced by Ethylene Glycol Diglycidyl Ether and Diethylenetriamine[J]. Ind. Crop. Prod., 2015, 74: 613–618

    Article  CAS  Google Scholar 

  30. Gao Q, Shi S Q, Zhang S, et al., Soybean Meal-based Adhesive Enhanced by MUF Resin[J]. J. Appl. Polym. Sci., 2012, 125(5): 3 676–3 681

    Article  CAS  Google Scholar 

  31. Song J, Tian H, Lei H, et al., Modification of Urea-formaldehyde Resin by nano MnO2[J]. Journal of Forestry Engineering, 2022, 7(2): 91–96

    Google Scholar 

  32. Liang J, Wu Z, Xi X, et al., Investigation of The Reaction between A Soy Based Protein Model Compound and Formaldehyde[J]. Wood Sci. Technol., 2019, 53(5): 1 061–1 077

    Article  CAS  Google Scholar 

  33. Li T, Guo X, Liang J, et al. Competitive Formation of the Methylene and Methylene Ether Bridges in the Urea-Formaldehyde Reaction in Alkaline Solution: A Combined Experimental and Theoretical Study[J]. Wood Sci. Technol., 2015, 49: 475–493

    Article  CAS  Google Scholar 

  34. Li T, Cao M, Liang J, et al., New Mechanism Proposed for the Base-Catalyzed Urea-Formaldehyde Condensation Reactions: A Theoretical Study[J]. Polymers, 2017, 9(6): 203

    Article  Google Scholar 

  35. Wang J, Du G, Yang H, et al., Synthesis and Adhesive Properties of Highly Branched Polyurea with Polyethyleneimine and Urea[J]. Journal of Forestry Engineering, 2022, 7(2): 97–102

    Google Scholar 

Download references

Author information

Authors and Affiliations

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

    Xue Deng  (邓雪), Lifen Li & Zhigang Wu  (吴志刚)

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

    Bengang Zhang & Hong Lei  (雷洪)

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

    Jiankun Liang

Authors
  1. Xue Deng  (邓雪)
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Bengang Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jiankun Liang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Lifen Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Zhigang Wu  (吴志刚)
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Hong Lei  (雷洪)
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

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

Additional information

Funded by the National Natural Science Foundation of China (32160348), the Department Program of Guizhou Province (ZK[2021]162 and [2019]2325), the Special Project of “Doctor Professor Service Group of Kaili University (BJFWT201906), and the Cultivation Project of Guizhou University of China ([2019]37)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Deng, X., Zhang, B., Liang, J. et al. The Crosslinking Mechanism of Camellia Oleifera Protein Adhesive with Amine Resins by 13C-NMR and ESI-MS. J. Wuhan Univ. Technol.-Mat. Sci. Edit. 38, 460–466 (2023). https://doi.org/10.1007/s11595-023-2719-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11595-023-2719-z

Key words

Search

Navigation