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Chemical modification of spruce wood with combination of mesyl chloride and poly(ε-caprolactone) for improvement of dimensional stability and water absorption properties

Yıl 2016, Cilt: 16 Sayı: 2, 0 - 0, 02.12.2016
https://doi.org/10.17475/kastorman.289764

Öz

Sustainability is an important issue for materials production which can be provided by using renewable resources such as wood. Wood is a natural material with excellent mechanical properties. However, humidity changes negatively affect wood’s dimensional stability. Water repellence and dimensional stability can be both improved by inserting hydrophobic molecules inside wood cell walls. In this study, a two-step modification were carried out by grafting a biodegradable polymer poly(ε-caprolactone) (PCL) onto the pre-treated wood cell walls by mesyl chloride. Confocal Raman imaging and spectroscopy were used to show the distribution of mesyl groups and poly(ε-caprolactone) within cell walls. The morphology of modified wood cell walls was monitored by scanning electron microscopy. Physical tests showed that the poly(ε-caprolactone) grafted wood has significantly better dimensional stability and water repellence compared to references.

Kaynakça

  • Butler, H.J., Ashton, L., Bird, B., Cinque, G., Curtis, K., Dorney, J., Esmonde-White, K., Fullwood, N.J., Gardner, B., Martin-Hirsch, P.L., Walsh, M.J., McAinsh, M.R., Stone, N., and Martin, F.L., 2016. Using Raman spectroscopy to characterize biological materials, Nature Protocols, 11, 664-687.
  • Cabane, E., Keplinger, T., Merk, V., Hass, P. and Burgert, I., 2014. Renewable and functional wood materials by grafting polymerization within cell walls, ChemSusChem, 7(4), 1020–1025.
  • Donath, S., Militz, H., and Mai, C., 2004. Wood modification with alkoxysilanes, Wood Science and Technology, 2004, 38, 555-566.
  • Duda, A., Penczek, S., Kowalski, A., and Libiszowski, J., 2000. Polymerizations of ε-caprolactone and L,L-dilactide initiated with stannous octoate and stannous butoxide― a comparison, Macromolecular Symposia, 153, 41-53.
  • Ermeydan, M.A., Cabane, E., Gierlinger, N., Koetz, J. and Burgert, I., 2014. Improvement of wood material properties via in situ polymerization of styrene into tosylated cell walls, RSC Advances, 4, 12981-12988.
  • Ermeydan, M.A., Cabane, E., Hass, P., Koetz, J., and 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 Chemistry, 16, 3313-3321.
  • Ermeydan, M.A., Cabane, E., Masic, A., Koetz, J. and Burgert, I., 2012, Flavonoid Insertion into Cell Walls Improves Wood Properties, ACS Applied Materials and Interfaces, 4, 5782-5789.
  • Fengel D. and Wegener, G., 1984. Wood: Chemistry, Ultrastructure, Reactions, ISBN 3-11-008481-3, W. de Gruyter, Berlin/New York.
  • Furuno, T. and Goto, T., 1979. Structure of the interface between wood and synthestic polymer. XII. Distribution of styrene polymer in the cell wall of wood-polymer composite(WPC) and dimensional stability, Mokuzai Gakkaishi, 1979, 25, 488–495.
  • Furuno, T., Imamura, Y., and Kajita, H., 2004. The modification of wood by treatment with low molecular weight phenol-formaldehyde resin: a properties enhancement with neutralized phenolic-resin and resin penetration into wood cell walls, Wood Science and Technology, 2004, 37, 349-361.
  • Gibson, L.J., 2012. The hierarchical structure and mechanics of plant materials, Journal of Royal Society Interface, 9(76), 2749-2766.
  • Gierlinger, N., and Schwanninger, M., 2007. The potential of Raman microscopy and Raman imaging in plant research, International Journal of Spectroscopy, 21, 69-89.
  • Hanai, K., Okuda, T., and Machida, K., 1975. Vibrational spectra of methanesulfonyl chloride and methanesulfonyl chloride-d3, Spectrochimica Acta, 31A, 1227-1232. 1975.
  • Hill, C.A.S., and Ormondroyd, G.A., 2004. Dimensional changes in Corsican pine (Pinus nigra Arnold) modified with acetic anhydride measured using a helium pycnometer, Holzforschung, 58, 544-547.
  • Hill, C.A.S., 2006. Wood Modification: Chemical, Thermal and Other Processes, ISBN: 978-0-470-02172-9, John Wiley & Sons, Chichester, England; Hoboken, NJ.
  • Keplinger, T., Cabane, E., Berg, J.K., Segmehl, J.S., Bock, P., and Burgert, I., 2016. Smart Hierarchical Bio-Based Materials by Formation of Stimuli-Responsive Hydrogels inside the Microporous Structure of Wood, Advance Materials Interfaces, 3, 1600233.
  • Keplinger, T., Cabane, E., Chanana, M., Hass, P., Merk, V., Gierlinger, N., Burgert, I., 2015. A versatile strategy for grafting polymers to wood cell walls, Acta Biomaterialia, 11, 256-263.
  • Kister, G., Cassanas, G., Bergounhon, M., Hoarau, D., and Vert, M., 2000. Structural characterization and hydrolytic degradation of solid copolymers of D,L-lactide-co-epsilon-caprolactone by RAman spectroscopy, Polymer, 41, 925-932.
  • Kricheldorf, H.R., Kreiser-Saunders, I., Sticker, A., 2000. SnOct2 –Initiated Polymerizations of Lactide: A Mechanistic Study, Macromolecules, 33, 702 -709.
  • Kusumi, R., Teramoto, Y., and Nishio, Y., 2011. Structural characterization of poly(ε-caprolactone)-grafted cellulose acetate and butyrate by solid-state 13C NMR, dynamic mechanical, and dielectric relaxation analyses, Polymer, 52, 5912-5921.
  • Labet, M., and Thielemans, W., 2009. Synthesis of polycaprolactone: a review, Chemical Society Reviews, 2009, 38, 3484-3504.
  • Lönnberg, H., Zhou, Q., Brumer, H., Teeri, T.T., Malmstrom E., and Hult, A., 2006. Grafting of cellulose fibers with poly(epsilon-caprolactone) and poly(L-lactic acid) via ring-opening polymerization, Biomacromolecules, 7, 2178-2185.
  • Makiguchi, K., Satoh, T., and Kakuchi, T., 2011. Diphenyl Phosphate as an Efficient Cationic Organocatalyst for Controlled/Living Ring-Opening Polymerization of δ-Valerolactone and ε-Caprolactone, Macromolecules, 44, 1999-2005.
  • Mantanis, G.I., Young, R.A., and Rowell, R.M., 1994. Swelling of wood, part II. Swelling in organic liquids, Holzforschung, 48, 480-490.
  • Nakagami, T. and Yokota, T., 1983. Estimation of crosslink-formation among wood components by dimesional stability merasurements. Mokuzai Gakkaishi, 29(3), 240-247.
  • Netscher, T., and Bohrer P., 2002. Towards Highly Activating Leaving Groups: Studies on the Preparation of Some Halogenated Alkyl Sulfonates, Molecules, 7, 601-617.
  • Nordstierna, L., Lande, S., Westin, M., Karlsson, O., Furo´, I., 2008. Towards novel wood-based materials: chemical bonds between lignin-like model molecules and poly(furfuryl alcohol) studied by NMR, Holzforschung, 62, 709–713.
  • Rowell R.M., 2005. Handbook of Wood Chemistry and Wood Composites, ISBN: 978-1-4398-5380-1, CRC Press, Boca Raton, Floridai, USA.
  • Rowell, R.M. 1984: Penetration and reactivity of cell wall components. Chapter 4, p. 175–210. In: Rowell, R. M., ed. Chemistry of Solid Wood. Adv. Chem. Ser. 207. American Chemical Society, Washington, DC.
  • Rowell, R.M., and Ellis, W.D., 1978. Determination of dimensional stability of wood using the water-soaking method. Wood and Fiber, 10(2), 104-111.
  • Schirp, A. and M.P. Wolcott. 2005. Influence of fungal decay and moisture absorption on mechanical properties of extruded wood-plastic composites. Wood and Fiber Science. 37(4), 643-652.
  • Schneider, M.H., and Brebner, K.I., 1985. Wood-polymer combinations: Bonding of alkoxysilane coupling agents to wood, Wood Science and Technology, 19, 67-73.
  • Storey, R.F., and Sherman, J.W., 2002. Kinetics and mechanism of the stannous octoate-catalyzed bulk polymerization of ε-caprolactone, Macromolecules, 35, 1504-1512.
  • Timmons, T.K., Meyer, J.A. and Cote, W.A., 1971. Polymer location in the wood polymer composite, Wood Science, 4, 13–24.
  • Wiltshire, J.T., and Qiao, G.G., 2006. Degradable core cross-linked star polymers via ring-opening polymerization, Macromolecules, 39, 4282-4285.
Yıl 2016, Cilt: 16 Sayı: 2, 0 - 0, 02.12.2016
https://doi.org/10.17475/kastorman.289764

Öz

Kaynakça

  • Butler, H.J., Ashton, L., Bird, B., Cinque, G., Curtis, K., Dorney, J., Esmonde-White, K., Fullwood, N.J., Gardner, B., Martin-Hirsch, P.L., Walsh, M.J., McAinsh, M.R., Stone, N., and Martin, F.L., 2016. Using Raman spectroscopy to characterize biological materials, Nature Protocols, 11, 664-687.
  • Cabane, E., Keplinger, T., Merk, V., Hass, P. and Burgert, I., 2014. Renewable and functional wood materials by grafting polymerization within cell walls, ChemSusChem, 7(4), 1020–1025.
  • Donath, S., Militz, H., and Mai, C., 2004. Wood modification with alkoxysilanes, Wood Science and Technology, 2004, 38, 555-566.
  • Duda, A., Penczek, S., Kowalski, A., and Libiszowski, J., 2000. Polymerizations of ε-caprolactone and L,L-dilactide initiated with stannous octoate and stannous butoxide― a comparison, Macromolecular Symposia, 153, 41-53.
  • Ermeydan, M.A., Cabane, E., Gierlinger, N., Koetz, J. and Burgert, I., 2014. Improvement of wood material properties via in situ polymerization of styrene into tosylated cell walls, RSC Advances, 4, 12981-12988.
  • Ermeydan, M.A., Cabane, E., Hass, P., Koetz, J., and 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 Chemistry, 16, 3313-3321.
  • Ermeydan, M.A., Cabane, E., Masic, A., Koetz, J. and Burgert, I., 2012, Flavonoid Insertion into Cell Walls Improves Wood Properties, ACS Applied Materials and Interfaces, 4, 5782-5789.
  • Fengel D. and Wegener, G., 1984. Wood: Chemistry, Ultrastructure, Reactions, ISBN 3-11-008481-3, W. de Gruyter, Berlin/New York.
  • Furuno, T. and Goto, T., 1979. Structure of the interface between wood and synthestic polymer. XII. Distribution of styrene polymer in the cell wall of wood-polymer composite(WPC) and dimensional stability, Mokuzai Gakkaishi, 1979, 25, 488–495.
  • Furuno, T., Imamura, Y., and Kajita, H., 2004. The modification of wood by treatment with low molecular weight phenol-formaldehyde resin: a properties enhancement with neutralized phenolic-resin and resin penetration into wood cell walls, Wood Science and Technology, 2004, 37, 349-361.
  • Gibson, L.J., 2012. The hierarchical structure and mechanics of plant materials, Journal of Royal Society Interface, 9(76), 2749-2766.
  • Gierlinger, N., and Schwanninger, M., 2007. The potential of Raman microscopy and Raman imaging in plant research, International Journal of Spectroscopy, 21, 69-89.
  • Hanai, K., Okuda, T., and Machida, K., 1975. Vibrational spectra of methanesulfonyl chloride and methanesulfonyl chloride-d3, Spectrochimica Acta, 31A, 1227-1232. 1975.
  • Hill, C.A.S., and Ormondroyd, G.A., 2004. Dimensional changes in Corsican pine (Pinus nigra Arnold) modified with acetic anhydride measured using a helium pycnometer, Holzforschung, 58, 544-547.
  • Hill, C.A.S., 2006. Wood Modification: Chemical, Thermal and Other Processes, ISBN: 978-0-470-02172-9, John Wiley & Sons, Chichester, England; Hoboken, NJ.
  • Keplinger, T., Cabane, E., Berg, J.K., Segmehl, J.S., Bock, P., and Burgert, I., 2016. Smart Hierarchical Bio-Based Materials by Formation of Stimuli-Responsive Hydrogels inside the Microporous Structure of Wood, Advance Materials Interfaces, 3, 1600233.
  • Keplinger, T., Cabane, E., Chanana, M., Hass, P., Merk, V., Gierlinger, N., Burgert, I., 2015. A versatile strategy for grafting polymers to wood cell walls, Acta Biomaterialia, 11, 256-263.
  • Kister, G., Cassanas, G., Bergounhon, M., Hoarau, D., and Vert, M., 2000. Structural characterization and hydrolytic degradation of solid copolymers of D,L-lactide-co-epsilon-caprolactone by RAman spectroscopy, Polymer, 41, 925-932.
  • Kricheldorf, H.R., Kreiser-Saunders, I., Sticker, A., 2000. SnOct2 –Initiated Polymerizations of Lactide: A Mechanistic Study, Macromolecules, 33, 702 -709.
  • Kusumi, R., Teramoto, Y., and Nishio, Y., 2011. Structural characterization of poly(ε-caprolactone)-grafted cellulose acetate and butyrate by solid-state 13C NMR, dynamic mechanical, and dielectric relaxation analyses, Polymer, 52, 5912-5921.
  • Labet, M., and Thielemans, W., 2009. Synthesis of polycaprolactone: a review, Chemical Society Reviews, 2009, 38, 3484-3504.
  • Lönnberg, H., Zhou, Q., Brumer, H., Teeri, T.T., Malmstrom E., and Hult, A., 2006. Grafting of cellulose fibers with poly(epsilon-caprolactone) and poly(L-lactic acid) via ring-opening polymerization, Biomacromolecules, 7, 2178-2185.
  • Makiguchi, K., Satoh, T., and Kakuchi, T., 2011. Diphenyl Phosphate as an Efficient Cationic Organocatalyst for Controlled/Living Ring-Opening Polymerization of δ-Valerolactone and ε-Caprolactone, Macromolecules, 44, 1999-2005.
  • Mantanis, G.I., Young, R.A., and Rowell, R.M., 1994. Swelling of wood, part II. Swelling in organic liquids, Holzforschung, 48, 480-490.
  • Nakagami, T. and Yokota, T., 1983. Estimation of crosslink-formation among wood components by dimesional stability merasurements. Mokuzai Gakkaishi, 29(3), 240-247.
  • Netscher, T., and Bohrer P., 2002. Towards Highly Activating Leaving Groups: Studies on the Preparation of Some Halogenated Alkyl Sulfonates, Molecules, 7, 601-617.
  • Nordstierna, L., Lande, S., Westin, M., Karlsson, O., Furo´, I., 2008. Towards novel wood-based materials: chemical bonds between lignin-like model molecules and poly(furfuryl alcohol) studied by NMR, Holzforschung, 62, 709–713.
  • Rowell R.M., 2005. Handbook of Wood Chemistry and Wood Composites, ISBN: 978-1-4398-5380-1, CRC Press, Boca Raton, Floridai, USA.
  • Rowell, R.M. 1984: Penetration and reactivity of cell wall components. Chapter 4, p. 175–210. In: Rowell, R. M., ed. Chemistry of Solid Wood. Adv. Chem. Ser. 207. American Chemical Society, Washington, DC.
  • Rowell, R.M., and Ellis, W.D., 1978. Determination of dimensional stability of wood using the water-soaking method. Wood and Fiber, 10(2), 104-111.
  • Schirp, A. and M.P. Wolcott. 2005. Influence of fungal decay and moisture absorption on mechanical properties of extruded wood-plastic composites. Wood and Fiber Science. 37(4), 643-652.
  • Schneider, M.H., and Brebner, K.I., 1985. Wood-polymer combinations: Bonding of alkoxysilane coupling agents to wood, Wood Science and Technology, 19, 67-73.
  • Storey, R.F., and Sherman, J.W., 2002. Kinetics and mechanism of the stannous octoate-catalyzed bulk polymerization of ε-caprolactone, Macromolecules, 35, 1504-1512.
  • Timmons, T.K., Meyer, J.A. and Cote, W.A., 1971. Polymer location in the wood polymer composite, Wood Science, 4, 13–24.
  • Wiltshire, J.T., and Qiao, G.G., 2006. Degradable core cross-linked star polymers via ring-opening polymerization, Macromolecules, 39, 4282-4285.
Toplam 35 adet kaynakça vardır.

Ayrıntılar

Bölüm Makaleler
Yazarlar

Mahmut Ali Ermeydan

Yayımlanma Tarihi 2 Aralık 2016
Yayımlandığı Sayı Yıl 2016 Cilt: 16 Sayı: 2

Kaynak Göster

APA 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 University Journal of Forestry Faculty, 16(2). https://doi.org/10.17475/kastorman.289764
AMA Ermeydan MA. Chemical modification of spruce wood with combination of mesyl chloride and poly(ε-caprolactone) for improvement of dimensional stability and water absorption properties. Kastamonu University Journal of Forestry Faculty. Aralık 2016;16(2). doi:10.17475/kastorman.289764
Chicago Ermeydan, Mahmut Ali. “Chemical Modification of Spruce Wood With Combination of Mesyl Chloride and poly(ε-Caprolactone) for Improvement of Dimensional Stability and Water Absorption Properties”. Kastamonu University Journal of Forestry Faculty 16, sy. 2 (Aralık 2016). https://doi.org/10.17475/kastorman.289764.
EndNote Ermeydan MA (01 Aralık 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 University Journal of Forestry Faculty 16 2
IEEE M. A. Ermeydan, “Chemical modification of spruce wood with combination of mesyl chloride and poly(ε-caprolactone) for improvement of dimensional stability and water absorption properties”, Kastamonu University Journal of Forestry Faculty, c. 16, sy. 2, 2016, doi: 10.17475/kastorman.289764.
ISNAD Ermeydan, Mahmut Ali. “Chemical Modification of Spruce Wood With Combination of Mesyl Chloride and poly(ε-Caprolactone) for Improvement of Dimensional Stability and Water Absorption Properties”. Kastamonu University Journal of Forestry Faculty 16/2 (Aralık 2016). https://doi.org/10.17475/kastorman.289764.
JAMA Ermeydan MA. Chemical modification of spruce wood with combination of mesyl chloride and poly(ε-caprolactone) for improvement of dimensional stability and water absorption properties. Kastamonu University Journal of Forestry Faculty. 2016;16. doi:10.17475/kastorman.289764.
MLA Ermeydan, Mahmut Ali. “Chemical Modification of Spruce Wood With Combination of Mesyl Chloride and poly(ε-Caprolactone) for Improvement of Dimensional Stability and Water Absorption Properties”. Kastamonu University Journal of Forestry Faculty, c. 16, sy. 2, 2016, doi:10.17475/kastorman.289764.
Vancouver Ermeydan MA. Chemical modification of spruce wood with combination of mesyl chloride and poly(ε-caprolactone) for improvement of dimensional stability and water absorption properties. Kastamonu University Journal of Forestry Faculty. 2016;16(2).

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