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Licensed Unlicensed Requires Authentication Published by De Gruyter July 26, 2016

Polyamidoamines (PAAs) functionalized with siloxanes as wood preservatives against fungi and insects

  • Laura Bergamonti , Alessia Berzolla , Elisabetta Chiappini , Elisabetta Feci , Lara Maistrello , Sabrina Palanti ORCID logo EMAIL logo , Giovanni Predieri and Giacomo Vaccari
From the journal Holzforschung

Abstract

A novel treatment based on polyamidoamines (PAAs) for the preservation of wood against fungi and insects with a broad protection functionality, low effective concentration, and low environmental impact has been developed. PAAs were synthesized by nucleophile addition of ethanolamine (EtA) and/or 3-aminopropyltriethoxysilane (APTES) to N,N′-methylene-bisacrylamide (MBA). The molar ratios in the tested formulation were: I) MBA:EtA=1:1; II) MBA:APTES=1:1; III) MBA:EtA:APTES=1:0.5:0.5. These formulations, characterized by ESI-MS, NMR, FT-IR, were tested against: (a) the wood decay fungi (Coniophora puteana, Coriolus versicolor, and Poria placenta); (b) the subterranean termite Reticulitermes lucifugus, and the drywood termite Kalotermes flavicollis; (c) the woodborer Stegobium paniceum. Tests in combination with leaching showed that formulation II and III can be utilized as fungal wood preservatives for use classes 2–3 (EN 335:2013). In addition, all PAAs formulations were equally effective in preserving wood against the subterranean termite, and formulation II was most effective against drywood termite. On the other hand, the formulation I showed good efficacy against S. paniceum.

Acknowledgments

The research described in this paper is part of a project named “Nanosolwood”, supported by RENNER SpA, Minerbio, Bologna (IT).

References

Bergamonti, L., Chiappini, E., Predieri, G., Palanti, S., Maistrello, L. (2015) Wood preservative composition. International Patent Application WO 2015/004590 A1.Search in Google Scholar

Bravery, A.F. A miniaturised wood-block test for the rapid evaluation of wood preservative fungicides. IRG/WP 2113. International Research Group on Wood Protection, Stockholm, Sweden, 1979.Search in Google Scholar

Cappelletto, E., Maggini, S., Girardi, F., Bochicchio, G., Tessadri, B., Di Maggio, R. (2013) Wood surface protection with different alkoxysilanes: a hydrophobic barrier. Cellulose 20:3131–3141.10.1007/s10570-013-0038-9Search in Google Scholar

Chiappini, E., Liotta, G., Reguzzi, M.C., Battisti, A. Insetti e restauro. Legno, carta, tessuti, pellame e altri materiali. Calderini Edagricole, Bologna, 2001.Search in Google Scholar

Clausen, C.A., Kartal, S.N., Arango, R.A., Green, F. (2011) The role of particle size of particulate nano-zinc oxide wood preservatives on termite mortality and leach resistance. Nanoscale Res. Lett. 6:465.10.1186/1556-276X-6-465Search in Google Scholar

Danusso, F., Ferruti, P. (1970) Synthesis of tertiary amine polymers. Polymer 11:88–113.10.1016/0032-3861(70)90029-7Search in Google Scholar

Deutsch, D.S., Siani, A., Fanson, P.T., Hirata, H., Matsumoto, S., Williams, C.T., Amiridis M.D. (2007) FT-IR investigation of the thermal decomposition of poly(amidoamine) dendrimers and dendrimer-metal nanocomposites supported on Al2O3 and ZrO2. J. Phys. Chem. C 111:4246–4255.10.1021/jp065853dSearch in Google Scholar

Donath, S., Militz, H., Mai, C. (2006) Treatment of wood with aminofunctional silanes for protection against wood destroying fungi. Holzforschung 60:210–216.10.1515/HF.2006.035Search in Google Scholar

Eaton, R.A., Hale, M.D.C. Wood: decay, pests, and protection. Chapman and Hall, London, 1993.Search in Google Scholar

European Committee for Standardization EN 47. Wood preservatives. Determination of the toxic values against larvae of Hylotrupes bajulus (Linnaeus). (Laboratory method). European Committee for Standardization, Brussels, Belgium, 2005.Search in Google Scholar

European Committee for Standardization EN 49-2. Wood preservatives – determination of the protective effectiveness against Anobium punctatum (De Geer) by egglaying and larval survival – part 2: application by impregnation (Laboratory method). European Committee for Standardization, Brussels, Belgium, 2015.Search in Google Scholar

European Committee for Standardization EN 84. Wood preservatives – Accelerated ageing of treated wood prior to biological testing. Leaching procedure. European Committee for Standardization, Brussels, Belgium, 1997.Search in Google Scholar

European Committee for Standardization EN 113. Wood preservatives. Test method for determining the protective effectiveness against wood destroying basidiomycetes – Determination of the toxic values. European Committee for Standardization, Brussels, Belgium, 2006.Search in Google Scholar

European Committee for Standardization EN 335. Durability of wood and wood-based products – use classes: definitions, application to solid wood and wood-based products. European Committee for Standardization, Brussels, Belgium, 2013.Search in Google Scholar

European Committee for Standardization EN 15866. Conservation of cultural property – test methods – colour measurement of surfaces. European Committee for Standardization, Brussels, Belgium, 2010.Search in Google Scholar

Ferruti, P., Marchisio, M.A., Duncan, R. (2002) Poly(amido-amine)s: biomedical applications. Macromol. Rapid Commun. 23:332–355.10.1007/978-1-4757-9510-3_5Search in Google Scholar

Girardi, F., Maggini, S., Della Volpe, C., Cappelletto, E., Mueller, K., Siboni, S., Di Maggio, R. (2011) Hybrid organic-inorganic materials on paper: surface and thermo-mechanical properties. J. Sol-Gel Sci. Technol. 60:315–323.10.1007/s10971-011-2563-zSearch in Google Scholar

Girardi, F., Cappelletto, E., Sandak, J., Bochicchio, G., Tessadri, B., Palanti, S., Feci, E., Di Maggio, R. R. (2014) Hybrid organic-inorganic materials as coatings for protecting wood. Prog. Org. Coat. 77:449–457.10.1016/j.porgcoat.2013.11.010Search in Google Scholar

Hadi, Y.S., Nawawi, D.S., Herliyana, E.N., Lawniczak, M. (1998) Termite attack resistance of four polystyrene-impregnated woods from Poland. For. Prod. J. 48:60–62.Search in Google Scholar

Hadi, Y.S., Westin, M., Rasyid, E. (2005) Resistance of furfurylated wood to termite attack. Forest Prod. J. 55:85–88.Search in Google Scholar

Hadi, Y.S., Nurhayati, T., Jasni, A., Yamamoto, H., Kamiya N. (2010a) Smoked wood resistance against termite. J. Trop. For. Sci. 22:127–132.Search in Google Scholar

Hadi, Y.S., Nurhayati, T., Jasni, J., Yamamoto, H., Kamiya, N. (2010b) Smoked wood as an alternative for wood protection against termites. Forest Prod. J. 60:496–500.10.13073/0015-7473-60.6.496Search in Google Scholar

Hadi, Y.S., Nurhayati, T., Jasni, A., Yamamoto, H., Kamiya N. (2012) Resistance of smoked wood to subterranean and dry-wood termite attack. Int. Biodeter. Biodegr. 70:79–81.10.1016/j.ibiod.2011.06.010Search in Google Scholar

Hill, C.A.S, Farahani, M.R.M., Hale, M.D.C. (2004) The use of organo alkoxysilane coupling agents for wood preservation. Holzforschung 58:316–325.10.1515/HF.2004.049Search in Google Scholar

Hughes, A. The tools at our disposal, Final Workshop Cost Action E22. Lisbon, Portugal, 2004.Search in Google Scholar

Hwang, W.J., Yoshimura, T., Tsunoda, K., Imamura, Y. (2006) Efficacy of two alkylammonium compounds in controlling the attack on wood by western drywood termite, Incisitermes minor (Isopterae: Kalotermitidae). Sociobiology 48:471–478.Search in Google Scholar

Kalaitzakis, D., Smonou, I. (2012) Chemoenzymatic synthesis of stegobinone and stegobiol, the natural sex pheromone of the drugstore beetle Stegobium paniceum L. Eur. J. Org. Chem. 1:43–46.10.1002/ejoc.201101319Search in Google Scholar

Kartal, S.N., Terzi, E., Yoshimura, T., Arango, R., Clausen, C.A, Green, F. (2012) Preliminary evaluation of storax and its constituents: Fungal decay, mold and termite resistance. Int. Biodeter. Biodegr. 70:47–54.10.1016/j.ibiod.2012.02.002Search in Google Scholar

Lebow, S., Arango, R., Woodward, B., Lebow, P., Ohno, K. (2015) Efficacy of alternatives to zinc naphthenate for dip treatment of wood packaging materials. Int. Biodeter. Biodegr. 104:371–376.10.1016/j.ibiod.2015.07.006Search in Google Scholar

Maistrello, L., Berzolla, A., Macias-Pavon, I., Vignali, F., Predieri, G., Chiappini, E. (2012a) Wood impregnated with metal chelates dissolved in organic media tested for termite resistance. J. Entomol. Acarol. Res. 43:277–285.10.4081/jear.2011.277Search in Google Scholar

Maistrello, L., Martini, L., Macías-Pavon, I., Bortolini, S., Marchettini, N. (2012b) Evaluation of polyphenols-rich natural compounds as treatments to prevent attacks by subterranean and drywood termites: preliminary results. J. Entomol. Acarol. Res. 43:261–267.10.4081/jear.2011.261Search in Google Scholar

Moein, S., Rust, M. (1992) The effect of wood degradation by fungi on the feeding and survival of the West-Indian drywood termite, Cryptotermes brevis (Isoptera, Kalotermitidae). Sociobiology 20:29–39.Search in Google Scholar

Müller, G., Schöpper, C., Vos, H., Kharazipour, A., Polle, A. (2009) FTIR-ATR spectroscopic analysis of chages in wood properties during particle- and fibreboard production of hard- and softwood trees. Bioresources 4:49–71.10.15376/biores.4.1.49-71Search in Google Scholar

Murugan, R., Mohan, S., Bigotto, A. (1998) FTIR and Polarised Raman Spectra of Acrylamide and Polyacrylamide. J. Korean Phys. Soc. 32:505–512.Search in Google Scholar

Obounou-Akong, F., Gérardin, P., Thévenon, M.F., Gérardin-Charbonnier, C. (2015) Hydrogel-based boron salt formulations for wood preservation. Wood Sci. Technol. 49:443–456.10.1007/s00226-015-0701-4Search in Google Scholar

Palanti, S., Feci, E., Predieri, G., Vignali, F. (2010) Copper anchored to amino-group functionalized silica gel as wood preservative against brown-rot decay. Maderas-Cienc. Tecnol. T. 12:259–266.10.4067/S0718-221X2010000300010Search in Google Scholar

Palanti, S., Predieri, G., Vignali, F., Feci, E., Casoli, A., Conti, E. (2011) Copper complexes grafted to functionalized silica gel as wood preservatives against the brown rot fungus Coniophora puteana. Wood Sci. Technol. 45:707–718.10.1007/s00226-010-0396-5Search in Google Scholar

Pandey, K.K. (1999) A study of chemical structure of soft and hardwood and wood polymers by FTIR spectroscopy. J. Appl. Polym. Sci. 71:1969–1975.10.1002/(SICI)1097-4628(19990321)71:12<1969::AID-APP6>3.0.CO;2-DSearch 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

Pernak, J., Zabielska-Mateljuc, J., Kropacs, A., Foksowicz-Flaczyk, J. (2004) Ionic liquid in wood preservation. Holzforschung 52:286–291.10.1515/HF.2004.044Search in Google Scholar

Rahman, I.A., Jafarzadeh, M., Sipaut, C. S. (2009) Synthesis of organo-functionalized nanosilica via cocondensation modification using aminopropyltriethoxysilane (APTES). Ceram. Int. 35:1883–1888.10.1016/j.ceramint.2008.10.028Search in Google Scholar

Robinson, W.H. Urban entomology. Chapman and Hall, London, 1996.10.1007/978-1-4613-0437-1Search in Google Scholar

Sèbe, G., Brook, M.A. (2001) Hydrophobization of wood surfaces: covalent grafting of silicone polymers. Wood Sci. Technol. 35:269–28.10.1007/s002260100091Search in Google Scholar

Suhasman, S., Nadi, Y.S., Massijaya, M.Y., Santoso, A. (2012) Binder less particleboard esistance to termite attack. For. Prod. J. 62:412–415.Search in Google Scholar

Sunarta, S., Darmadji, P., Uehara, T., Katoh, S. (2011) Production and characterization of palm fruit shell bio-oil for wood preservation. For. Prod. J. 61:180–184.10.13073/0015-7473-61.2.180Search in Google Scholar

Tsunoda, K., Nishimoto, K. (1987) Effectiveness of alkylammonium compounds as above-ground wood preservatives. J. Japan Wood Res. Soc. 33:589–595.Search in Google Scholar

Unger, B., Bücker M., Reinsch, S., Hübert, T. (2013) Chemical aspects of wood modification by sol-gel-derived silica. Wood Sci. Technol. 47:83–104.10.1007/s00226-012-0486-7Search in Google Scholar

Vignali, F., Predieri, G., Baratto, M.C., Basosi, R., Müller, K., Callone, E, Palanti, S., Feci E. (2011) Interpenetration of wood with NH2R-functionalized silica xerogels anchoring copper(II) for preservation purposes. J. Sol-Gel Sci. Techn. 60:445–456.10.1007/s10971-011-2557-xSearch in Google Scholar

Received: 2016-1-12
Accepted: 2016-6-22
Published Online: 2016-7-26
Published in Print: 2017-1-1

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