Functionalisation of wood by reaction with 3-isocyanatopropyltriethoxysilane: Grafting and hydrolysis of the triethoxysilane end groups
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Philippe Tingaut
Abstract
The chemical modification of maritime pine sapwood (Pinus pinaster Soland) with 3-isocyanatopropyltriethoxysilane (IPTES) and its subsequent hydrolysis were investigated. The formation of urethane linkages after the carbamoylation reaction was confirmed by Fourier-transform infrared (FTIR) spectroscopy. The weight percent gain (WPG) obtained was found to be commensurate with the quantity of IPTES in the reagent solution. Swelling measurements combined with scanning electron microscopy-energy dispersive X-ray (SEM-EDX) analysis showed that the reaction occurred within the wood cell walls. Hydrolysis of the grafted triethoxysilane ends in highly carbamoylated wood was also envisaged: the modifications generated after prolonged contact with water were studied by FTIR spectroscopy and 13C and 29Si nuclear magnetic resonance cross-polarisation with magic-angle spinning (NMR CP MAS) analysis. The chemical environments found for silicon (Si–OH, Si–OEt or Si–OSi) before and after hydrolysis were thus identified and a schematic representation of the silicon structures most often encountered in modified wood was proposed.
References
Arkles, B. (1977) Tailoring surfaces with silanes. Chemtech7:766–778.Search in Google Scholar
Bazant, V., Chvalovsky, V., Rathowsky, J. Organosilicon Compounds. Academic Press, New York, 1965.Search in Google Scholar
Cai, M., Ho, M., Pemberton, J.E. (2000) Surface vibrational spectroscopy of alkylsilane layers covalently bonded to monolayers of (3-mercaptopropyl)trimethoxysilane on Ag substrates. Langmuir16:3446–3453.10.1021/la991075nSearch in Google Scholar
Denes, A.R., Tshabalala, M.A., Rowell, R., Denes, F., Young, R.A. (1999) Hexamethyldisiloxane-plasma coating of wood surfaces for creating water repellent characteristics. Holzforschung53:318–326.10.1515/HF.1999.052Search in Google Scholar
Derouet, D., Forgeard, S., Brosse, J.-C., Emery, J., Buzare, J.-Y. (1998) Application of solid-state NMR (13C and 29Si CP/MAS NMR) spectroscopy to the characterization of alkenyltrialkoxysilane and trialkoxysilyl-terminated polyisoprene grafting onto silica microparticles. J. Polym. Sci. A Polym. Chem.36:437–453.10.1002/(SICI)1099-0518(199802)36:3<437::AID-POLA8>3.0.CO;2-OSearch in Google Scholar
Douskey, M.C., Gebhard, M.S., McCormick, A.V., Lange, B.C., Whitman, D.W., Schure, M.R., Beshah, K. (2002) Spectroscopic studies of a novel cyclic oligomer with pendant alkoxysilane groups. Prog. Org. Coat.45:145–157.10.1016/S0300-9440(02)00104-2Search in Google Scholar
Cho, D.L., Sjoblom, E. (1990) Plasma treatment of wood. J. Appl. Polym. Sci. Appl. Polym. Symp.46:461–472.10.1002/app.1990.070460023Search in Google Scholar
Hellgren, J.M., Olofsson, K., Sundberg B. (2004) Patterns of auxin distribution during gravitational induction of reaction wood in poplar and pine. Plant Physiol.135:212–220.10.1104/pp.104.038927Search 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. Holzforschung58:316–325.10.1515/HF.2004.049Search in Google Scholar
Hon, D.N.-S. – Chemical Modification of Lignocellulosic Materials. Marcel Dekker, New York, 1996.Search in Google Scholar
Hook, J.H. (1996) A 29Si NMR study of the sol-gel polymerisation rates of substituted ethoxysilanes. J. Non-Cryst. Solids195:1–15.10.1016/0022-3093(95)00508-0Search in Google Scholar
Lu, J.Z., Wu, Q., McNabb, H.S. (2000) Chemical coupling in wood fiber and polymer composites: a review of coupling agents and treatments. Wood Fiber Sci.32(1):88–104.Search in Google Scholar
Mai, C., Militz, H. (2004) Modification of wood with silicon compounds. Treatment systems based on organic silicon compounds – a review. Wood Sci. Technol.37:453–461.Search in Google Scholar
Miyashita, H., Suzuki, M. (1999) Improvement of dimensional stability and fire retardancy by γ-methacryloxypropyl trimethoxysilane for Cryptomeria japonica D. Don and its application to durability of adhesive bond plywood. Mokuzai Gakkaishi45(3):251–260.Search in Google Scholar
Miyashita, H., Ohmi, M., Tominaga, H., Sawatari, A., Suzuki, M., Kawarada, K., Mizumoto, K. (2000) Distribution of silicon atoms in sugi wood treated with γ-methacryloxypropyl trimethoxysilane and its fire retardancy. Mokuzai Gakkaishi46(5):449–455.Search in Google Scholar
Ogiso, K., Saka, S. (1994) Wood-inorganic composites prepared by sol-gel process III. Effects of chemical bonds between wood and inorganic substances on property enhancement. Mokuzai Gakkaishi40:1100–1106.Search in Google Scholar
Oyane, A., Minoda, M., Miyamoto, T., Takahashi, R., Nakanishi, K., Kim, H.-M., Kokubo, T., Nakamura, T. (1999) Apatite formation on ethylene-vinyl alcohol copolymer modified with silanol groups. J. Biomater. Mater. Res.47(3):367–373.10.1002/(SICI)1097-4636(19991205)47:3<367::AID-JBM11>3.0.CO;2-ASearch in Google Scholar
Oyane, A., Kawashita, M., Nakanishi, K., Nakanishi, K., Kokubo, T., Minoda, M., Miyamoto, T., Nakamura, T. (2003) Bonelike apatite formation on ethylene-vinyl alcohol copolymer modified with silane coupling agent and calcium silicate solutions. Biomaterials24:1729–1735.10.1016/S0142-9612(02)00581-1Search in Google Scholar
Rowell, R.M. The Chemistry of Solid Wood. Advances in Chemistry Series No. 207. American Chemical Society, New York, 1984.10.1021/ba-1984-0207Search in Google Scholar
Saka, S., Yakake, Y. (1993) Wood-inorganic compositesprepared by sol-gel process III. Chemically modified wood-inorganic composites. Mokuzai Gakkaishi75:308–314.Search in Google Scholar
Sèbe, G., De Jéso, B. (2000) The dimensional stabilisation of maritime pine sapwood (Pinus pinaster) by chemical reaction with organosilicon compounds. Holzforschung54:474–480.10.1515/HF.2000.080Search in Google Scholar
Sèbe, G., Brook, M.A. (2001) Hydrophobization of wood surfaces: covalent grafting of silicone polymers. Wood Sci. Technol.35(3):269–282.10.1007/s002260100091Search in Google Scholar
Sèbe, G., Tingaut, P., Safou-Tchiama, R, Pétraud, M., Grelier, S., De Jéso, B. (2004) Chemical reaction of maritime pine sapwood (Pinus pinaster Soland) with alkoxysilane molecules: A study of chemical pathways. Holzforschung58:511–518.10.1515/HF.2004.078Search in Google Scholar
Tissot, I., Reymond, J.P., Lebfevre, F., Bourgeat-Lami, E. (2002) SiOH-functionalized polystyrene latexes. A step toward the synthesis of hollow silica nanoparticles. Chem. Mater.14:1325–1331.Search in Google Scholar
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Articles in the same Issue
- Chemical changes in silver birch (Betula pendula Roth) wood caused by hydrogen peroxide bleaching and monitored by color measurement (CIELab) and UV-Vis, FTIR and UVRR spectroscopy
- Hydrophobisation and densification of wood by different chemical treatments
- Functionalisation of wood by reaction with 3-isocyanatopropyltriethoxysilane: Grafting and hydrolysis of the triethoxysilane end groups
- Isolation and fractionation of lignosulfonates by amine extraction and ultrafiltration: A comparative study
- Bioactive phenolic substances in industrially important tree species. Part 4: Identification of two new 7-hydroxy divanillyl butyrolactol lignans in some spruce, fir, and pine species
- Characterization of physiological functions of sapwood IV: Formation and accumulation of lignans in sapwood of Cryptomeria japonica (L.f.) D. Don after felling
- X-ray scattering studies of thermally modified Scots pine (Pinus sylvestris L.)
- Differences in acoustic velocity by resonance and transit-time methods in an anisotropic laminated wood medium
- Parallel-plate rheology of latex films bonded to wood
- An assessment of the feasibility of ultrasound as a defect detector in lumber
- Vibrational properties of green wood in high-temperature water vapor
- The stiffness modulus in Norway spruce as a function of year ring
- Strain analysis in bulk forming of wood
- Decay fungi from playground wood products in service using 28S rDNA sequence analysis
- Effect of climatic variables on chromated copper arsenate (CCA) leaching during above-ground exposure
- Protic ionic liquids with organic anion as wood preservative
Articles in the same Issue
- Chemical changes in silver birch (Betula pendula Roth) wood caused by hydrogen peroxide bleaching and monitored by color measurement (CIELab) and UV-Vis, FTIR and UVRR spectroscopy
- Hydrophobisation and densification of wood by different chemical treatments
- Functionalisation of wood by reaction with 3-isocyanatopropyltriethoxysilane: Grafting and hydrolysis of the triethoxysilane end groups
- Isolation and fractionation of lignosulfonates by amine extraction and ultrafiltration: A comparative study
- Bioactive phenolic substances in industrially important tree species. Part 4: Identification of two new 7-hydroxy divanillyl butyrolactol lignans in some spruce, fir, and pine species
- Characterization of physiological functions of sapwood IV: Formation and accumulation of lignans in sapwood of Cryptomeria japonica (L.f.) D. Don after felling
- X-ray scattering studies of thermally modified Scots pine (Pinus sylvestris L.)
- Differences in acoustic velocity by resonance and transit-time methods in an anisotropic laminated wood medium
- Parallel-plate rheology of latex films bonded to wood
- An assessment of the feasibility of ultrasound as a defect detector in lumber
- Vibrational properties of green wood in high-temperature water vapor
- The stiffness modulus in Norway spruce as a function of year ring
- Strain analysis in bulk forming of wood
- Decay fungi from playground wood products in service using 28S rDNA sequence analysis
- Effect of climatic variables on chromated copper arsenate (CCA) leaching during above-ground exposure
- Protic ionic liquids with organic anion as wood preservative