Abstract
This paper deals with an original and non-biocidal chemical treatment consisting of a vacuum/pressure impregnation step of beech wood with a water-borne mixture made from heat-activated condensation of succinic anhydride (SA) and glycerol (G). Chemical structures of adducts were established using matrix-assisted laser desorption ionization time-of-flight mass spectroscopy (MALDI-TOF) investigations. Beech wood was impregnated and cured in order to induce in situ polymerization of glycerol/succinic adducts (GSA) in the cell walls, leading to the formation of polyglycerol succinate (PGS) polyester. Various treatment conditions were investigated depending on the duration (6–72 h) and curing temperature (103–160°C). Weight percent gains (WPGs) ranging between 40 and 60% were obtained. Attenuated total reflectance-middle infrared spectroscopy (ATR-MIR) and carbon-13 nuclear magnetic resonance (13C-NMR) spectroscopy confirmed polyester formation. A curing temperature of 160°C was found to be the best condition to totally avoid polymer leaching, and brought the anti-swelling efficiency (ASE) up to 64%. Decay resistance of PGS-treated wood against Trametes versicolor and Coniophora puteana was also strongly temperature and time dependent: performances fit with the EN113 standard requirements if a curing temperature of 160°C was applied.
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: The research leading to these results was supported by funding from the WoodWisdom-Net Research Program, which is a transnational R&D program jointly funded by national funding organizations within the framework of the ERA-NET+Action WoodWisdom-Net+. LERMaB is supported by a grant overseen by the French National Research Agency (ANR) as part of the ‘‘Investissements d’Avenir’’ program (ANR-11-LABX-0002-01, Lab of Excellence ARBRE).
Employment or leadership: None declared.
Honorarium: None declared.
References
Agach, M., Delbaere, S., Marinkovic, S., Estrine, B., Nardello-Rataj, V. (2012) Characterization, stability and ecotoxic properties of readily biodegradable branched oligoesters based on bio-sourced succinic acid and glycerol. Polym. Degrad. Stabil. 97: 1956–1963.10.1016/j.polymdegradstab.2012.03.026Search in Google Scholar
Behrens, R.H. (2015) The raised potential for vector-borne diseases in European Travelers Following the EU’s Biocide Directive on DEET Dosing. J. Travel Med. 22:203–205.10.1111/jtm.12191Search in Google Scholar
Carnahan, M.A., Grinstaff, M.W. (2001) Synthesis and characterization of poly(glycerol-succinic acid) dendrimers. Macromolecules 34:7648–7655.10.1021/ma010848nSearch in Google Scholar
El Hage, R., Chrusciel, L., Desharnais, L., Brosse, N. (2010) Effect of autohydrolysis of miscanthus x giganteus on lignin structure and organosolv delignification. Biores. Technol. 101:9321–9329.10.1016/j.biortech.2010.06.143Search in Google Scholar
Gilardi, G., Abis, L., Cass, A. (1995) C-13 CP/MAS solid-state NMR and FT-IR spectroscopy of wood cell-wall biodegradation. Enzyme Microb. Tech. 17:268–275.10.1016/0141-0229(94)00019-NSearch in Google Scholar
Guerrero, P., Arana, P., O’Grady, M.N., Kerry, J.P., De la Caba, K. (2015) Valorization of industrial by-products: development of active coatings to reduce food losses. J. Clean. Prod. 100: 179–184.10.1016/j.jclepro.2015.03.049Search in Google Scholar
Guo, W., Xiao, Z., Wentzel, M., Emmerich, L., Xie, Y., Militz, H. (2019) Modification of Scots pine with activated glucose and citric acid: physical and mechanical properties. BioResources 14:3445–3458.10.15376/biores.14.2.3445-3458Search in Google Scholar
Hakkou, M., Pétrissans, M., Zoulalian, A., Gérardin, P. (2005) Investigation of wood wettability changes during heat treatment on the basis of chemical analysis. Polym. Degrad. Stabil. 89:1–5.10.1016/j.polymdegradstab.2004.10.017Search in Google Scholar
Halpern, J.M., Urbanski, R., Weinstock, A.K., Iwig, D.F., Mathers, R.T., von Recum, H.A. (2014) A biodegradable thermoset polymer made by esterification of citric acid and glycerol. J. Biomed. Mater. Res. A 102:1467–1477.10.1002/jbm.a.34821Search in Google Scholar PubMed PubMed Central
Hill, C.A.S., Malone, S. (1998) The chemical modification of scots pine with succinic anhydride or octenyl succinic anhydride. I. Dimensional stabilization. Holzforschung 52:427–433.10.1515/hfsg.1998.52.4.427Search in Google Scholar
Jiang, M., Ma, J., Wu, M., Liu, R., Liang, L., Xin, F., Zhang, W., Jia, H., Dong, W. (2017) Progress of succinic acid production from renewable resources: metabolic and fermentative strategies. Bioresour. Technol. 245:1710–1717.10.1016/j.biortech.2017.05.209Search in Google Scholar PubMed
Kluppel, A., Mai, C. (2013) The influence of curing conditions on the chemical distribution in wood modified with thermosetting resins. Wood Sci. Technol. 47:643–658.10.1007/s00226-013-0530-2Search in Google Scholar
Lande, S., Westin, M., Schneider, M. (2004) Properties of furfurylated wood. Scand. J. For. Res. 19:22–30.10.1080/0282758041001915Search in Google Scholar
Larnøy, E., Karaca, A., Gobakken, L.R., Hill, C.A.S. (2018) Polyesterification of wood using sorbitol and citric acid under aqueous conditions. Int. Wood Prod. J. 9:66–73.10.1080/20426445.2018.1475918Search in Google Scholar
L’Hostis, C., Thevenon, M.F., Fredon, E., Gerardin, P. (2018) Improvement of beech wood properties by in situ formation of polyesters of citric acid and tartaric acid in combination with glycerol. Holzforschung 72:291–299.10.1515/hf-2017-0081Search in Google Scholar
Li, Y., Cook, W.D., Moorhoff, C., Huang, W.C., Chen, Q.Z. (2012) Synthesis, characterization and properties of biocompatible poly(glycerol sebacate) pre-polymer and gel. Polym. Int. 62:534–547.10.1002/pi.4419Search in Google Scholar
Liu, X.Y., Timar, M.C., Varodi, A.M., Sawyer, G. (2017) An investigation of accelerated temperature-induced ageing of four wood species: colour and FTIR. Wood Sci. Technol. 51:357–378.10.1007/s00226-016-0867-4Search in Google Scholar
NF EN 113 (1996) Wood preservatives – determination of toxic values of wood preservatives against wood destroying basidiomycetes cultured on agar medium. European Committee for Standardization.Search in Google Scholar
NF EN 84 (1997) Wood preservatives – accelerated ageing of treated wood prior to biological testing – leaching procedure. European Committee for Standardization.Search in Google Scholar
NF X 41-568 (2014) AFNOR, Wood preservatives – laboratory method for obtaining samples for analysis to measure losses by leaching into water or synthetic sea water.Search in Google Scholar
Noël, M., Fredon, E., Mougel, E., Masson, D., Masson, E., Delmotte, L. (2009a) Lactic acid/wood-based composite material. Part 1: synthesis and characterization. Bioresource Technol. 100:4711–4716.10.1016/j.biortech.2009.04.040Search in Google Scholar PubMed
Noël, M., Mougel, E., Fredon, E., Masson, D., Masson, E. (2009b) Lactic acid/wood-based composite material. Part 2: physical and mechanical performance. Bioresource Technol. 100:4717–4722.10.1016/j.biortech.2009.04.042Search in Google Scholar PubMed
Noël, M., Grigsby, W., Vitkeviciute, I., Volkmer, T. (2015) Modifying wood with bio-polyesters: analysis and performance. Int. Wood Prod. J. 6:14–20.10.1179/2042645314Y.0000000086Search in Google Scholar
Okoye, P.U., Hameed, B.H. (2016) Review on recent progress in catalytic carboxylation and acetylation of glycerol as a byproduct of biodiesel production. Renew. Sustain. Energy Rev. 53:558–574.10.1016/j.rser.2015.08.064Search in Google Scholar
Pandey, K.K., Pitman, A.J. (2003) FTIR studies of the changes in wood chemistry following decay by brown-rot and white-rot fungi. Int. Biodeter. Biodegr. 52:151–160.10.1016/S0964-8305(03)00052-0Search in Google Scholar
Roussel, C., Marchetti, V., Lemor, A., Wozniak, E., Loubinoux, B., Gérardin, P. (2001) Chemical modification of wood by polyglycerol/maleic anhydride treatment. Holzforschung 55:57–62.10.1515/HF.2001.009Search in Google Scholar
Rowell, R.R. (2014) Acetylation of wood – a review. Int. J. Lignocell. Prod. 1:1–27.Search in Google Scholar
Sandberg, D., Kutnar, A., Mantanis, G. (2017) Wood modification technologies – a review. iForest 10:895–908.10.3832/ifor2380-010Search in Google Scholar
Santoni, I., Callone, E., Sandak, A., Sandak, J., Dire, S. (2015) Solid state NMR and IR characterization of wood polymer structure in relation to tree provenance. Carbohydr. Polym. 117:710–721.10.1016/j.carbpol.2014.10.057Search in Google Scholar PubMed
Schultz, T.P., Nicholas, D.D., Preston, A.F. (2007) A brief review of the past, present and future of wood preservation. Pest Manag. Sci. 63:784–788.10.1002/ps.1386Search in Google Scholar PubMed
Sejati, P.S., Imbert, A., Gérardin-Charbonnier, C., Dumarçay, S., Fredon, E., Masson, E., Nandika, D., Priadi, T., Gérardin, P. (2017) Tartaric acid catalyzed furfurylation of beech wood. Wood Sci. Technol. 51:379–394.10.1007/s00226-016-0871-8Search in Google Scholar
Tjeerdsma, B.F., Militz, H. (2005) Chemical changes in hydrothermal treated wood: FTIR analysis of combined hydrothermal and dry heat-treated wood. Holz Roh. Werkst. 63:102–111.10.1007/s00107-004-0532-8Search in Google Scholar
Valerio, O., Horvath, T., Pond, C., Misra, M. (2015) Improved utilization of crude glycerol from biodiesel industries: synthesis and characterization of sustainable biobased polyesters. Ind. Crops Prod. 78:141–147.10.1016/j.indcrop.2015.10.019Search in Google Scholar
Yates, M.R., Barlow, C.Y. (2013) Life cycle assessments of biodegradable, commercial biopolymers – a critical review. Resour. Conserv. Recycl. 78:54–66.10.1016/j.resconrec.2013.06.010Search in Google Scholar
Zhang, T., Howell, B.A., Dumistracu, A., Martin, S.J. (2014) Synthesis and characterization of glycerol-adipic hyperbranched polyesters. Polymer 55:5065–5072.10.1016/j.polymer.2014.08.036Search in Google Scholar
Zia, K.M., Noreen, A., Zuber, M., Tabasum, S., Mujahid, M. (2016) Recent developments and future prospects on bio-based polyesters derived from renewable resources: a review. Int. J. Biol. Macromol. 82:1028–1040.10.1016/j.ijbiomac.2015.10.040Search in Google Scholar PubMed
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