Abstract
In this study, in situ graft polymerization of ε-caprolactone (CL) was studied for its potential to limit boric acid (BA) leaching from wood, and to increase the dimensional stability and biological durability of wood against Coniophora puteana and Trametes versicolor fungi. For this purpose, CL monomer with/without BA was impregnated into wood, and the monomer was polymerized in wood cell walls using various methods and combinations of reactants. It was found that biodegradable polycaprolactone (PCL) grafting at high monomer concentrations could inhibit fungal degradation of wood cell walls, as well as improve the dimensional stability of wood up to 55% and reduce water uptake (WU) by about 50%. However, inductively coupled plasma-optical emission spectrometry (ICP-OES) analysis revealed that in situ graft polymerization of CL is not an effective method to prevent BA leaching from wood.
Acknowledgments
Thanks are due to Prof. Dr. John Dunlop from the Salzburg University, Austria, for helping us improve the English of the manuscript.
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: This work was supported by the Bursa Technical University (grant no. BTU-BAP 2016-01-008), Bursa, Turkey.
Employment or leadership: None declared.
Honorarium: None declared.
References
Abdel-Motaal, F.F., El-Sayed, M.A., El-Zayat, S.A., Ito, S. (2014) Biodegradation of poly (ε-caprolactone) (PCL) film and foam plastic by Pseudozyma japonica sp. nov., a novel cutinolytic ustilaginomycetous yeast species. 3 Biotech 4:507–512.10.1007/s13205-013-0182-9Search in Google Scholar
Assessment Report (2009) Inclusion of active substances in Annex I or IA to Directive 98/8/EC, Boric acid Product-type 8 (Wood preservative), Retrieved December 28, 2018 from http://dissemination.echa.europa.eu/Biocides/ActiveSubstances/ 0009-08/0009-08_Assessment_Report.pdf.Search in Google Scholar
Baldrian, P. (2003) Interactions of heavy metals with white-rot fungi. Enzyme Microb. Technol. 32:78–91.10.1016/S0141-0229(02)00245-4Search in Google Scholar
Bergman, R. (2010) Drying and control of moisture content and dimensional changes. In: Wood Handbook – Wood as an Engineering Material. Forest Products Laboratory, Madison, USA. pp. 1–20.Search in Google Scholar
BS-EN 350 (2016) Durability of wood and wood-based products – testing and classification of the durability to biological agents of wood and wood-based materials.Search in Google Scholar
Cui, W., Kamdem, P. (1999) Bioefficiency of Boric acid grafted on to wood. In The 30th Annual Meeting of International Research Group on Wood Preservation. Rosenheim, Germany, Document No: IRG/WP 99-30202.Search in Google Scholar
Dong, Y., Qin, Y., Wang, K., Yan, Y., Zhang, S., Li, J., Zhang, S. (2016) Assessment of the performance of furfurylated wood and acetylated wood: comparison among four fast-growing wood species. BioResources 11:3679–3690.10.15376/biores.11.2.3679-3690Search in Google Scholar
Ermeydan, M.A. (2016) Chemical modification of spruce wood with combination of mesyl chloride and poly(ε-caprolactone) for improvement of dimensional stability and water absorption properties. Kastamonu Univ. J. Forestry Faculty 16:541–552.10.17475/kastorman.289764Search in Google Scholar
Ermeydan, M.A., Tomak, E.D. (2016) The combined effects of boron and polymer modification on decay resistance and properties of wood. In 16th International Materials Symposium, Denizli, Turkey. pp. 1574–1581.Search in Google Scholar
Ermeydan, M.A., Cabane, E., Hass, P., Koetz, J., Burgert, I. (2014) Fully biodegradable modification of wood for improvement of dimensional stability and water absorption properties by poly(ε-caprolactone) grafting into the cell walls. Green Chem. 16:3313–3321.10.1039/c4gc00194jSearch in Google Scholar
Ermeydan, M.A., Tomak, E.D., Kartal, Z.N. (2019) Wood property improvement of siberian pine by combination of boric acid impregnation and in-situ polymerization of ε-caprolactone. J.Polytechnic. 22:157–161.10.2339/politeknik.386966Search in Google Scholar
Fengel, D., Wegener, G. Wood: Chemistry, Ultrastructure, Reactions. Verlag Kessel, Remagen-Oberwinter, 2003.Search in Google Scholar
Fromm, J., Rockel, B., Lautner, S., Windeisen, E., Wanner, G. (2003) Lignin distribution in wood cell walls determined by TEM and backscattered SEM techniques. J. Struct. Biol. 143:77–84.10.1016/S1047-8477(03)00119-9Search in Google Scholar
Gadd, G.M., Gray, D.J., Newby, P.J. (1990) Role of melanin in fungal biosorption of tributyltin chloride. Appl. Microbiol. Biotechnol. 34:116–121.10.1007/BF00170934Search in Google Scholar
Gierlinger, N., Keplinger, T., Harrington, M. (2012) Imaging of plant cell walls by confocal Raman microscopy. Nat. Protoc. 7:1694–1708.10.1038/nprot.2012.092Search in Google Scholar PubMed
Hanninen, T., Kontturi, E., Vuorinen, T. (2011) Distribution of lignin and its coniferyl alcohol and coniferyl aldehyde groups in Picea abies and Pinus sylvestris as observed by Raman imaging. Phytochemistry 72:1889–1895.10.1016/j.phytochem.2011.05.005Search in Google Scholar PubMed
Hill, C.A.S. Wood Modification: Chemical, Thermal and Other Processes. Wiley, Chichester, UK, 2006.10.1002/0470021748Search in Google Scholar
Homan, W.J., Jorissen, A.J.M. (2004) Wood modification developments. Heron 49:361–386.Search in Google Scholar
Humar, M. (2017) Protection of the bio-based material, Chapter 4. In: Performance of Bio-based Building Materials. Ed. Jones, D., Brischke, C. Woodhead Publishing, Duxford, UK. pp. 187–203.10.1016/B978-0-08-100982-6.00004-5Search in Google Scholar
Humar, M., Melcher E. (2017) Material protection. In: Performance of Bio-based Building Materials. Ed. Jones, D., Brischke, C.Woodhead Publishing, Duxford, UK. pp. 203–247.Search in Google Scholar
Kartal, S.N., Yoshimura, T., Imamura, Y. (2004) Decay and termite resistance of boron-treated and chemically modified wood by in situ co-polymerization of allyl glycidyl ether (AGE) with methyl methacrylate (MMA). Int. Biodeter. Biodegr. 53:111–117.10.1016/j.ibiod.2003.09.004Search in Google Scholar
Kister, G., Cassanas, G., Bergounhon, M., Hoarau, D., Vert, M. (2000) Structural characterization and hydrolytic degradation of solid copolymers of d,l-lactide-co-ε-caprolactone by Raman spectroscopy. Polymer 41:925–932.10.1016/S0032-3861(99)00223-2Search in Google Scholar
Krzisnik, D., Lesar, B., Thaler, N., Humar, M. (2018) Micro and material climate monitoring in wooden buildings in sub-alpine environments. Constr. Build. Mater. 166:188–195.10.1016/j.conbuildmat.2018.01.118Search in Google Scholar
Leja, K., Lewandowicz, G. (2010) Polymer biodegradation and biodegradable polymers – a review. Polish J. Environ. Stud. 19:255–266.Search in Google Scholar
Lesar, B., Kralj, P., Humar, M. (2009) Montan wax improves performance of boron-based wood preservatives. Int. Biodeter. Biodegr. 63:306–310.10.1016/j.ibiod.2008.10.006Search in Google Scholar
Lloyd, J.D., Fogel, J.L. (2005) Wood preservative concentrate. Patent number: 6896908, United States.Search in Google Scholar
Ozaki, S.K., Yalinkilic, M.K., Imamura, Y., Souza, M.F. (2001) Effect of boron compounds-furfuryl alcohol treatment of wood on dimensional stability, termite resistance and boron leachability. In 32. IRG Annual Meeting, May, Nara, Japan, IRG-WP 01-40195.Search in Google Scholar
Palmans, E., Mares, G., Poppe, J., Höfte, M. (1995) Biodegradation of xenobiotics by heavy metal resistant higher fungi. In Ninth Forum for Applied Biotechnology September 27–29, 1995, Gent, Belgium. Proceedings part II, p. 2593.Search in Google Scholar
Peylo, A., Willeitner, H. (1995) The problem of reducing the leachability of boron by water repellents. Holzforschung 49:211–216.10.1515/hfsg.1995.49.3.211Search in Google Scholar
Råberg, U., Hafrén, J. (2008) Biodegradation and appearance of plastic treated solid wood. Int. Biodeter. Biodegr. 62:210–213.10.1016/j.ibiod.2007.12.006Search in Google Scholar
Reinprecht, L., Kizlink, J. (1999) Synthesis and anti-fungal screening test of organotin dithiocarbamates. Drevársky Výskum 44:67–74.Search in Google Scholar
Reshmi, C.R., Sundaran, S.P., Juraij, A., Athiyanathil, S. (2017) Fabrication of superhydrophobic polycaprolactone/beeswax electrospun membranes for high-efficiency oil/water separation. RSC Adv. 7:2092–2102.10.1039/C6RA26123JSearch in Google Scholar
Rowell, R. Handbook of Wood Chemistry and Wood Composites, 2nd ed. CRC Press, Boca Raton, FL, 2012.10.1201/b12487Search in Google Scholar
Rowell, R. (2014) Acetylation of wood – a review. Int. J. Lignocellul. Prod. 1:1–27.Search in Google Scholar
Rowell, R.M., Ellis, W.D. (1978) Determination of dimensional stabilization of wood using the water-soak method. Wood Fiber 10:104–111.Search in Google Scholar
Salami, M.A., Kaveian, F., Rafienia, M., Saber-Samandari, S., Khandan, A., Naeimi, M. (2017) Electrospun polycaprolactone/lignin-based nanocomposite as a novel tissue scaffold for biomedical applications. J. Med. Signals Sens. 7:228–238.10.4103/jmss.JMSS_11_17Search in Google Scholar
Storey, R.F., Sherman, J.W. (2002) Kinetics and mechanism of the stannous octoate-catalyzed bulk polymerization of ε-caprolactone. Macromolecules 35:1504–1512.10.1021/ma010986cSearch in Google Scholar
Temiz, A., Terziev, N., Jacobsen, B., Eikenes, M. (2006) Weathering, water absorption, and durability of silicon, acetylated, and heat-treated wood. J. Appl. Polym. Sci. 102:4506–4513.10.1002/app.24878Search in Google Scholar
Temiz, A., Alfredsen, G., Eikenes, M., Terziev, N. (2008) Decay resistance of wood treated with boric acid and tall oil derivates. Bioresour. Technol. 99:2102–2106.10.1016/j.biortech.2007.08.052Search in Google Scholar PubMed
Thevenon, M.F., Pizzi, A., Haluk, J.P., Zaremski, A. (1998) Normalized biological tests of protein borates wood preservatives. Holz Roh Werk. 56:162.10.1007/s001070050290Search in Google Scholar
Tomak, E.D. (2014) Changes in chemical composition of decayed Scots pine and beech wood. Sci. Eng. Compos. Mater. 21:589–595.10.1515/secm-2013-0180Search in Google Scholar
Tudor, D., Robinson, S.C., Cooper, P.A. (2012) The influence of moisture content variation on fungal pigment formation in spalted wood. AMB Express 2:69.10.1186/2191-0855-2-69Search in Google Scholar PubMed PubMed Central
Yalinkilic, M.K., Yoshimura, T., Takahashi, M. (1998a) Enhancement of the biological resistance of wood by phenylboronic acid treatment, J. Wood Sci. 44:152–157.10.1007/BF00526262Search in Google Scholar
Yalinkilic, M.K., Dwianto, W., Imamura, Y., Takahashi, M. (1998b) A new process for in situ polymerization of vinyl monomers in wood to delay boron leaching. Document International Research Group on Wood Preservation, IRG/WP 98-40110.Search in Google Scholar
Yalinkilic, M.K., Imamura, Y., Takahashi, M., Yalinkilic, A.C. (1999) In situ polymerization of vinyl monomers during compressive deformation of wood treated with boric acid to delay boron leaching. Forest Prod. J. 49:43–51.Search in Google Scholar
Zabel, R.A., Morrell, J.J. (1992) Wood deterioration agents. In: Wood Microbiology: Decay and its Prevention. Academic Press, San Diego, CL.10.1016/B978-0-12-775210-5.50006-5Search in Google Scholar
Zuo, Z., Zhou, X., Zuo, C. (1999) On the role of boric acid in the copper-tin alloy bath. Wuhan Univ. J. Nat. Sci. 4:211–215.10.1007/BF02841503Search in Google Scholar
Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/hf-2018-0231).
©2019 Walter de Gruyter GmbH, Berlin/Boston
