Skip to main content

Advertisement

Log in

Neutrals influence on the water resistance coefficient of phenol-formaldehyde resin modified by wood pyrolysis liquid products

  • Original Article
  • Published:
Biomass Conversion and Biorefinery Aims and scope Submit manuscript

Abstract

This article presents the results of the investigation of the properties of phenol-formaldehyde resin, obtained using the phenol-replacing fraction. A two-step method was developed for phenol-replacing fraction separation from liquid pyrolysis products with a yield up to 15%, and this fraction was used in the phenol-formaldehyde resin synthesis. Then, a work was conducted for the removal of neutrals from the modified phenol-formaldehyde resin with organic solvents, n-hexane and benzene. As a result, benzene was defined as a more efficient solvent because it removed more aromatics, like ethers and substituted phenols, that cannot react and worsen the glue line water resistance. Benzene dissolved 3.2% weight of the resin, and n-hexane dissolved 2.5% weight. The removal of neutrals increased the water resistance coefficient by more than 60%, so neutrals have a considerable effect on the resin properties. The results can be used for production of resin from renewable feedstock with the similar properties with the traditional resin.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Doronin YG, Svitkina MM, Miroshnichenko SN (1979) Synthetic resins in wood processing: a guide. Lesnaya promyshlennost’. 208 p. (in Russian)

  2. Weber M, Weber M, Kleine-Boymann M (2004) Phenol/Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCN. doi:https://doi.org/10.1002/14356007.a19_299.pub2

  3. Grachev AN, Zabelkin SA, Iakovleva AY, Fayzrahmanova GM, Bashkirov VN (2014) Resole phenol-formaldehyde resin glue line strength when modified by wood pyrolysis piqued products. Vestnik Kazanskogo Technologicheskogo Universiteta 16:27–29 (In Russian)

    Google Scholar 

  4. Bridgwater AV, Peacocke GVC (2000) Fast pyrolysis processes for biomass. Renew Sust Energ Rev 4(1):1–73. https://doi.org/10.1016/S1364-0321(99)00007-6

    Article  Google Scholar 

  5. Stücker A, Schütt F, Saake B, Lehnen R (2016) Lignins from enzymatic hydrolysis and alkaline extraction of steam refined poplar wood: utilization in lignin-phenol-formaldehyde resins. Ind Crop Prod 85:300–308

    Article  Google Scholar 

  6. Varfolomeev MA, Emel'yanenko VN, Musin TR, Gerasimov AV, Nurgaliev DK, Grachev AN, Makarov AA, Zabelkin SA (2015) Thermal analysis and calorimetric study of the combustion of hydrolytic wood lignin and products of its pyrolysis. Chem Technol Fuels Oils 51(1):140–145

    Article  Google Scholar 

  7. Fayzrakhmanova GM, Zabelkin SA, Grachev AN, Bashkirov VN (2016) A study of the properties of a composite asphalt binder using liquid products of wood fast pyrolysis. Polymer Science, Series D: Glues and Sealing Materials 9(2):181–184

    Article  Google Scholar 

  8. Amen-Chen C, Pakdel H, Roy C (2001) Production of monomeric phenols by thermochemical conversion of biomass: a review. Bioresour Technol 79:277–299

    Article  Google Scholar 

  9. Fardhyanti DS, Triwibowo B, Prasetiawan H, Chafidz A, Andriyani S, Cahyani NN (2019) Improving the quality of bio-oil produced from rice husk pyrolysis by extraction of its phenolic compounds. Jurnal Bahan Alam Terbarukan JBAT 8(2):90–100

    Article  Google Scholar 

  10. La Ifa, Setiawati Yani, Mandasini, Zakir Sabara, Nurjannah Nurjannah, & Andi Rusnaenah. Production of phenol from liquid smoke resulted by the pyrolysis of cashew nut shells. IOP Conf. Series: Earth and Environmental Science 2018 IOP Conf. Ser.: Earth Environ. Sci. 175 012033.

  11. Awasthia A, Dhyania V, Biswasa B, Kumara J, Bhaskar T (2019) Production of phenolic compounds using waste coir pith: estimation of kinetic and thermodynamic parameters. Bioresour Technol 274:173–179

    Article  Google Scholar 

  12. Zabelkin SA, Grachev AN, Bikbulatova GM, Yakovleva AE, Makarov AA, Bashkirov VN (2018) Resole-type phenol–formaldehyde resin with neutralized liquid products of fast pyrolysis of birch wood. Polymer Science, Series D 11:131–134

    Article  Google Scholar 

  13. Zhang W, Ma Y, Wang C, Li S, Zhang M, Chu F (2013) Preparation and properties of lignin–phenol–formaldehyde resins based on different biorefinery residues of agricultural biomass. Ind Crop Prod 43:326–333

    Article  Google Scholar 

  14. Zabelkin S, Grachev A, Fayzrakhmanova G, Makarov A, Bashkirov V (2016) Application of the water-insoluble pyrolysis oil fraction as an organic binder. Constr Build Mater 102:59–64

    Article  Google Scholar 

  15. Grachev AN, Varfolomeev MA, Emel’yanov DA, Zabelkin SA, Gilfanov MF, Nuriyakhmetov RA (2017) Joint thermal treatment of heavy oil and liquid products of fast wood pyrolysis for producing fuels and chemicals. Chem Technol Fuels Oils 53:638–645

    Article  Google Scholar 

  16. Lee JH, Jeon J, Kim SJ (2011) Green adhesives using tannin and cashew nut shell liquid for environment-friendly furniture materials. Korean Furniture Soc 22:219–229

    Google Scholar 

  17. Bisanda ETN, Ogola WO, Tesha JV (2003) Characterisation of tannin adhesive blends for particle board applications. Cem Concr Res 25:593–598

    Article  Google Scholar 

  18. Vazquez G, Antorrena G, Gonzalez J et al (1996) Tannin based adhesives for bonding high moisture eucalyptus veneers: influence of tannin extraction and press conditions. Holz Roh Werkst 54:93–97

    Article  Google Scholar 

  19. Uvarov IP, Gordon LV (1962) Wood resins (synthetic products based on wood chemical phenols). Moscow: Goslesbumizdat. 84 p. (In Russian)

  20. Nakos P, Tsiantzi S, Athanassiadou E. (2001) Wood adhesives made with pyrolysis oils. In: Proceedings of 3rd European Wood-based Panel Symposium, Sep 12–14; European Panel Federation & Wilhelm Klauditz Institute, Hannover, pp. 1–8

  21. Chaouch M, Diouf PN, Laghdir A, Yin S (2014) Bio-oil from whole-tree feedstock in resol-type phenolic resins. Journal of Applied Polymer Science. 10.1002/app.40014

  22. Cui Y, Chang J, Wang W (2016) Fabrication of glass fiber reinforced composited based on bio-oil phenol formaldehyde resin. Materials 9:886. https://doi.org/10.3390/ma9110886

    Article  Google Scholar 

  23. Lee W, Tseng I, Kao Y, Lee Y, Hu M (2014) Synthesis of alcohol-soluble resins from pyrolysis oil of Cunninghamia lanceolate wood and properties of molding plates made of resin-impregnated materials. Holzforschung. 68(2):217–222. https://doi.org/10.1515/hf-2013-0068

    Article  Google Scholar 

  24. Sukhbaatar B, Steele PH, Kim MG (2009) Use of lignin separated from bio-oil in oriented strand board binder phenol-formaldehyde adhesives. BioResources. 4:789–804

    Google Scholar 

  25. Aslan M, Özbay G, Ayrilmis N (2015) Adhesive characteristics and bonding performance of phenol formaldehyde modified with phenol-rich fraction of crude bio-oil. J Adhes Sci Technol 29:2679–2691. https://doi.org/10.1080/01694243.2015.1080474

    Article  Google Scholar 

  26. Guzelciftci B, Park K, Kim J(2020) Production of phenol-rich bio-oil via a two-stage pyrolysis of wood. Energy 200. doi: https://doi.org/10.1016/j.energy.2020.117536

  27. Kim J (2014) Production, separation and applications of phenolic-rich bio-oil – A review. Bioresour Technol 178:90–98. https://doi.org/10.1016/j.biortech.2014.08.121

    Article  Google Scholar 

  28. Chum HL, Black SK (1990) Process for fractionating fast-pyrolysis oils and products derived from, USA patent 4, 942, 269. July 17

  29. Suzuki T, Hiroshi N, Yamada T, Homma T (1992) Preparation of wood tar-based phenol-resin adhesives. Mokuzai Gak 38:321–324

    Google Scholar 

  30. Cheng S, Yuan Z, Anderson M, Leitch M, Xu C (2012) Synthesis of biobased phenolic resins/adhesives with methylolated wood-derived bio-oil. J Appl Polym Sci 126:E431–E441. https://doi.org/10.1002/app.35655

    Article  Google Scholar 

  31. Choi G, Oh S, Lee S, Kim J (2015) Production of bio-based phenolic resin and activated carbon from bio-oil and biochar derived from fast pyrolysis of palm kernel shells. Bioresour Technol 178:99–107

    Article  Google Scholar 

  32. Farag S, Chaouki J (2014) Economics evaluation for on-site pyrolysis of kraft lignin to value-added chemicals. Bioresour Technol 175:254–261. https://doi.org/10.1016/j.biortech.2014.10.096

    Article  Google Scholar 

  33. Vithanage AE, Chowdhury E, Alejo LD, Pomeroy PC, DeSisto WJ, Frederick BG, Gramlich WM (2017) Renewably sourced phenolic resins from lignin bio-oil. J Appl Polym Sci, DOI: 10.1002/APP.44827

  34. Effendi A, Gerhauser H, Bridgwater AV (2007) Production of renewable phenolic resins by thermochemical conversion of biomass: a review. Renew Sustain Energy Rev. doi: 10.1016/j.rser.2007.04.008

  35. Zhang W, Ma Y, Xu Y, Wang C, Chu F (2013) Lignocellulosic ethanol residue-based lignin–phenol–formaldehyde resin adhesive. Int J Adhes Adhes 40:11–18

    Article  Google Scholar 

  36. Feghali E. et al. (2020) Thermosetting polymers from lignin model compounds and depolymerized lignins. In: Serrano L., Luque R., Sels B. (eds) Lignin chemistry. Topics in Current Chemistry Collections. Springer, Cham

  37. Valeeva AR, Grachev AN, Zabelkin SA, Bashkirov VN, Sabirzyanova AI (2020) Determination of phenol substitution level influence by wood pyrolysis liquid products on phenol-formaldehyde resin strength. Derevoobrabatyvayuschaya Promyshlennost 16:88–95 (In Russian)

    Google Scholar 

  38. Grachev AN et al. A fast ablative pyrolysis plant for decentralized processing of biomass into biochar and biooil. EUBCE 2019; 27TH European Biomass Conference and Exhibition. Lisbon – Portugal: 164

  39. ASTM E 203-16 Standard test method for water using volumetric Karl Fischer titration.

  40. ASTM D5266-13 Standard practice for estimating the percentage of wood failure in adhesive bonded joints

  41. Dahiya A (2015) Bioenergy. Biomass to biofuels. 1st Edition. Academic Press

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Sergey Zabelkin.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zabelkin, S., Valeeva, A., Sabirzyanova, A. et al. Neutrals influence on the water resistance coefficient of phenol-formaldehyde resin modified by wood pyrolysis liquid products. Biomass Conv. Bioref. 12, 5563–5570 (2022). https://doi.org/10.1007/s13399-020-01025-0

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13399-020-01025-0

Keywords

Navigation