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Soy protein isolate-based polyamides as wood adhesives

  • Xuedong Xi
  • Antonio PizziEmail author
  • Christine Gerardin
  • Xinyi Chen
  • Siham Amirou
Original
  • 17 Downloads

Abstract

Soy protein isolate was reacted first with maleic anhydride and then hexamethylenediamine to synthesis soy protein isolate-based polyamides (SPIPA). Its bonding properties were measured by preparing laboratory three-layer plywood. Furthermore, a silane coupling agent (KH560), citric acid and maleic anhydride were added as cross-linkers to the SPIPA glue mix before hot pressing the panels. ATR FT-MIR and MALDI-ToF were used to determine the structures of the SPIPA, and thermomechanical analysis was used to analyze its thermomechanical properties. The results show that maleic anhydride reacts with amino acids in the soy protein molecule and then reacts with hexamethylenediamine to form carbamate-structured polyamides. This is confirmed by the ATR FT-MIR and MALDI-ToF results. Moreover, structural analysis indicates that a large number of branched structures are formed and occur in the SPIPA, rendering possible the formation of a network during curing, ensuring the bonding performance of the adhesive. The SPIPA adhesive presented good bonding strength and water resistance above the standard requirements of China National Standard GB/T 9846-2015. In particular, when maleic anhydride was added as a cross-linking agent, namely the SPIPA-MA adhesive, the panels’ dry and wet shear strengths were improved so that it can be considered as a suitable soy protein-based wood adhesive.

Notes

Acknowledgements

The first and the fourth author thank the China Scholarship Council for the study bursary granted to them. The LERMAB of the University of Lorraine is supported by a grant by the French National Research Agency (ANR) as part of the Laboratory of Excellence (Labex) ARBRE. This paper was also funded by ERA CoBioTech, L’Agence nationale de la recherche (ANR) under WooBAdh title.

References

  1. Bel-Hassen R, Boufi S, Salon MCB, Abdelmouleh M, Belgacem MN (2008) Adsorption of silane onto cellulose fibers. II. The effect of pH on silane hydrolysis, condensation, and adsorption behavior. J Appl Polym Sci 108(3):1958–1968CrossRefGoogle Scholar
  2. Butler PJG, Harris JI, Hartley BS, Leberman R (1969) The use of maleic anhydride for the reversible blocking of amino groups on polypeptide chains. Biochem J 112(5):679PubMedPubMedCentralGoogle Scholar
  3. China National Standard GB/T 14074 (2006) Testing methods for wood adhesives and their resins. Standardization Administration of the Peoples Republic of ChinaGoogle Scholar
  4. China National Standard GB/T 17657 (1999) Test methods for evaluating the properties of wood-based panels and surface decorated wood-based panels. Standardization Administration of the Peoples Republic of China (SAC)Google Scholar
  5. China National Standard GB/T 4897.5-2003 (2003) Requirements for load-bearing boards for use in humid conditions. Standardization Administration of the Peoples Republic of China (SAC)Google Scholar
  6. Creighton TE (1996) Proteins: structures and molecular properties, 2nd edn. W.H. Freeman, New YorkGoogle Scholar
  7. Del Menezzi C, Amirou S, Pizzi A, Xi X, Delmotte L (2018) Reactions with wood carbohydrates and lignin of citric acid as a bond promoter of wood veneer panels. Polymers 10(8):833CrossRefGoogle Scholar
  8. EN 312.2003 (2003) Particleboards—specifications. European Committee for StandardisationGoogle Scholar
  9. EN 636:2012 (2012) Plywood—specifications. European Committee for StandardisationGoogle Scholar
  10. Eslah F, Jonoobi M, Faezipour M, Afsharpour M, Enayati AA (2016) Preparation and development of a chemically modified bio-adhesive derived from soybean flour protein. Int J Adhes Adhes 71:48–54CrossRefGoogle Scholar
  11. Gao ZH, Zhang YH, Fang B, Zhang LP, Shi J (2015) The effects of thermal-acid treatment and crosslinking on the water resistance of soybean protein. Ind Crop Prod 74:122–131CrossRefGoogle Scholar
  12. Gui C, Wang G, Wu D, Zhu J, Liu X (2013) Synthesis of a bio-based polyamidoamine-epichlorohydrin resin and its application for soy-based adhesives. Int J Adhes Adhes 44:237–242CrossRefGoogle Scholar
  13. Hemmilä V, Adamopoulos S, Karlsson O, Kumar A (2017) Development of sustainable bio-adhesives for engineered wood panels—a Review. RSC Adv 7(61):38604–38630CrossRefGoogle Scholar
  14. Hettiarachchy NS, Kalapathy U, Myers DJ (1995) Alkali-modified soy protein with improved adhesive and hydrophobic properties. J Am Oil Chem Soc 72(12):1461–1464CrossRefGoogle Scholar
  15. Kamoun C, Pizzi A (2000) Particleboard IB forecast by TMA bending in MUF adhesives curing. Eur J Wood Prod 58(4):288–289CrossRefGoogle Scholar
  16. Lecourt M, Pizzi A, Humphrey P (2003) Comparison of TMA and ABES as forecasting systems of wood bonding effectiveness. Eur J Wood Prod 61(1):75–76CrossRefGoogle Scholar
  17. Lei H, Frazier CE (2015) Curing behavior of melamine-urea-formaldehyde (MUF) resin adhesive. Int J Adhes Adhes 62:40–44CrossRefGoogle Scholar
  18. Lei H, Pizzi A, Navarrete P, Rigolet S, Redl A, Wagner A (2010) Gluten protein adhesives for wood panels. J Adhes Sci Technol 24(8–10):1583–1596CrossRefGoogle Scholar
  19. Lei H, Du G, Wu Z, Xi X, Dong Z (2014) Cross-linked soy-based wood adhesives for plywood. Int J Adhes Adhes 50:199–203CrossRefGoogle Scholar
  20. Li K, Peshkova S, Geng X (2004) Investigation of soy protein-Kymene® adhesive systems for wood composites. J Am Oil Chem Soc 81(5):487–491CrossRefGoogle Scholar
  21. Lin Q, Chen N, Bian L, Fan M (2012) Development and mechanism characterization of high performance soy-based bio-adhesives. Int J Adhes Adhes 34:11–16CrossRefGoogle Scholar
  22. Liu Y, Li K (2002) Chemical modification of soy protein for wood adhesives. Macromol Rapid Commun 23(13):739–742CrossRefGoogle Scholar
  23. Liu Y, Li K (2007) Development and characterization of adhesives from soy protein for bonding wood. Int J Adhes Adhes 27(1):59–67CrossRefGoogle Scholar
  24. Liu W, Mohanty AK, Askeland P, Drzal LT, Misra M (2008) Modification of soy protein plastic with functional monomer with reactive extrusion. J Polym Environ 16(3):177–182CrossRefGoogle Scholar
  25. Pizzi A (2006) Recent developments in eco-efficient bio-based adhesives for wood bonding: opportunities and issues. J Adhes Sci Technol 20(8):829–846CrossRefGoogle Scholar
  26. Pizzi A (2016) Wood products and green chemistry. Ann For Sci 73(1):185–203CrossRefGoogle Scholar
  27. Pizzi A, Garcia R, Deglise X (1998) Thermomechanical analysis of entanglement networks: correlation of some calculated and experimental parameters. J Appl Polym Sci 67(9):1673–1678CrossRefGoogle Scholar
  28. Salon MCB, Abdelmouleh M, Boufi S, Belgacem MN, Gandini A (2005) Silane adsorption onto cellulose fibers: hydrolysis and condensation reactions. J Colloid Interface Sci 289(1):249–261CrossRefGoogle Scholar
  29. Schmidt V, Giacomelli C, Soldi V (2005) Thermal stability of films formed by soy protein isolate–sodium dodecyl sulfate. Polymer Degrad Stab 87(1):25–31CrossRefGoogle Scholar
  30. Simon C, George B, Pizzi A (2002) Copolymerization in UF/pMDI adhesives networks. J Appl Polymer Sci 86(14):3681–3688CrossRefGoogle Scholar
  31. Sun X, Bian K (1999) Shear strength and water resistance of modified soy protein adhesives. J Am Oil Chem Soc 76(8):977–980CrossRefGoogle Scholar
  32. Umemura K, Ueda T, Kawai S (2012a) Characterization of wood-based molding bonded with citric acid. J Wood Sci 58(1):38–45CrossRefGoogle Scholar
  33. Umemura K, Ueda T, Munawar SS, Kawai S (2012b) Application of citric acid as natural adhesive for wood. J Appl Polymer Sci 123(4):1991–1996CrossRefGoogle Scholar
  34. Umemura K, Sugihara O, Kawai S (2013) Investigation of a new natural adhesive composed of citric acid and sucrose for particleboard. J Wood Sci 59(3):203–208CrossRefGoogle Scholar
  35. Vnučec D, Kutnar A, Goršek A (2017) Soy-based adhesives for wood-bonding—a review. J Adhes Sci Technol 31(8):910–931CrossRefGoogle Scholar
  36. Xi X, Pizzi A, Delmotte L (2018) Isocyanate-free polyurethane coatings and adhesives from mono-and di-saccharides. Polymers 10(4):402CrossRefGoogle Scholar
  37. Xi X, Wu Z, Pizzi A, Gerardin C, Lei H, Zhang B, Du G (2019) Non-isocyanate polyurethane adhesive from sucrose used for particleboard. Wood Sci Technol 53(2):393–405CrossRefGoogle Scholar
  38. Xie Y, Hill CA, Xiao Z, Militz H, Mai C (2010) Silane coupling agents used for natural fiber/polymer composites: a review. Compos A Appl Sci Manuf 41(7):806–819CrossRefGoogle Scholar
  39. Zhong Z, Sun XS, Wang D, Ratto JA (2003) Wet strength and water resistance of modified soy protein adhesives and effects of drying treatment. J Polym Environ 11(4):137–144CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.LERMABUniversity of LorraineÉpinalFrance
  2. 2.Yunnan Key Laboratory of Wood Adhesives and Glue ProductsSouthwest Forestry UniversityKunmingChina
  3. 3.LERMABUniversity of LorraineNancyFrance

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