Chemical improvement of surfaces. Part 5: surfactants as structural lead for wood hydrophobization – covalent modification with p-alkylated benzoates

Christian Kaldun; Martin Söftje; Jan C. Namyslo; Dieter E. Kaufmann

doi:10.1515/hf-2019-0196

Article

Chemical improvement of surfaces. Part 5: surfactants as structural lead for wood hydrophobization – covalent modification with p-alkylated benzoates

Christian Kaldun , Martin Söftje , Jan C. Namyslo and Dieter E. Kaufmann

Published/Copyright: December 9, 2019

Published by

Become an author with De Gruyter Brill

Submit Manuscript Author Information Explore this Subject

From the journal Holzforschung Volume 74 Issue 7

Abstract

For a durable improvement of the hydrophobization properties of wood Scots pine (Pinus sylvestris L.) sapwood veneer chips were covalently modified with surfactant-like p-alkylated benzoates and a corresponding 4-cyanophenyl derivative. These esterification reactions of wood hydroxyl groups at varied temperatures and different reaction times afforded weight percent gains (WPG) ranging from 8 to 44% and quantities of covalently bonded organomaterials (QCO) of 0.3–2.6 mmol per gram, respectively. The successful covalent attachment of the functional precursors was proven by attenuated total reflection-infrared spectroscopy (ATR-IR), while the improvement of hydrophobicity was demonstrated by resulting contact angles (CAs) in a range from 113 to 150°.

Keywords: alkylation; attenuated total reflection IR (ATR-IR); contact angle (CA); covalent fixation; esterification; hydrophobization; quantity of covalently bonded organomaterial (QCO)

Acknowledgements

We appreciate the support given by the Institute of Non-Metallic Materials, Clausthal University of Technology (Germany), for contact angle measurements. We gratefully acknowledge H. Militz and C. Mai from the Section of Wood Biology and Wood Products, Georg-August-University Göttingen (Germany) for providing the veneer of Scots pine sapwood.

Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: This work was financially supported by Clausthal University of Technology, Germany.
Employment or leadership: None declared.
Honorarium: None declared.

References

Abdul Khalil, H.P.S., Bakare, I.O., Khairul, A., Issam, A.M., Bhat, I.-ul-Haq. (2011a) Effect of anhydride modification on the thermal stability of cultivated Acacia mangium. J. Wood Chem. Technol. 31:154–171.10.1080/02773813.2010.510586Search in Google Scholar

Abdul Khalil, H.P.S., Khairul, A., Bakare, I.O., Bhat, I.-ul-Haq. (2011b) Thermal, spectroscopic, and flexural properties of anhydride modified cultivated Acacia spp. Wood Sci. Technol. 45: 597–606.10.1007/s00226-010-0365-zSearch in Google Scholar

Arni, P.C., Gray, J.D., Scougall, R.K. (1961) Chemical modification of wood. I. Use of trifluoricacetic anhydride in the esterification of wood by carboxylic acids. J. Appl. Chem. 11:157–169.10.1002/jctb.5010110501Search in Google Scholar

Çetin, N.S., Ozmen, N. (2001) Dimensional changes in Corsican and Scots Pine sapwood due to reaction with crotonic anhydride. Wood Sci. Technol. 35:257–267.10.1007/s002260100093Search in Google Scholar

Chang, H.-T., Chang, S.-T. (2002) Moisture excluding efficiency and dimensional stability of wood improved by acylation. Biores. Technol. 85:201–204.10.1016/S0960-8524(02)00085-8Search in Google Scholar

Chang, H.-T., Chang, S.-T. (2003) Improvements in dimensional stability and lightfastness of wood by butyrylation using microwave heating. J. Wood Sci. 49:455–460.10.1007/s10086-002-0504-8Search in Google Scholar

Dawson, B.S.W., Franich, R.A., Kroese, H.W., Steward, D. (1999) Reactivity of radiata pine sapwood towards carboxylic acid anhydrides. Holzforschung 53:195–198.10.1515/HF.1999.032Search in Google Scholar

Drafz, M.H.H., Dahle, S., Maus-Friedrichs, W., Namyslo, J.C., Kaufmann, D.E. (2012) Chemical improvement of surfaces. Part 2: permanent hydrophobization of wood by covalently bonded fluoroorganyl substituents. Holzforschung 66:727–733.10.1515/hf-2011-0216Search in Google Scholar

Eastham, G.R., Butler, I. (2008) Novel carbonylation ligands and their use in the carbonylation of ethylenically unsaturated compounds. Lucite International UK Limited, WO002008065448 A1:88.Search in Google Scholar

Eranna, P.B., Pandey, K.K. (2012) Solvent-free chemical modification of wood by acetic and butyric anhydride with iodine as catalyst. Holzforschung 66:967–971.10.1515/hf-2011-0223Search in Google Scholar

Funakoshi, H., Shiraishi, N., Norimoto, M., Aoki, T., Hayashi, H., Yokota, T. (1979) Studies on the thermoplasticization of wood. Holzforschung 33:159–166.10.1515/hfsg.1979.33.5.159Search in Google Scholar

Grimm, J., Heidebrecht, R.W., Mampreian, D.M., Methot, J.L., Miller, T., Otte, K.M., Peterson, S., Siliphaivanh, P., Wilson, K.J., Witter, D.J. (2009) Silicon derivatives as histone deacetylase inhibitors. Merck & Co., Inc., WO2009/020589 A1:68.Search in Google Scholar

Habu, N., Nagasawa, Y., Samejima, M., Nakanishi, T.M. (2006) The effect of substituent distribution on the decay resistance of chemically modified wood. Int. Biodet. Biodeg. 57:57–62.10.1016/j.ibiod.2005.10.009Search in Google Scholar

Hammett, L.P. (1937) The effect of structure upon the reactions of organic compounds. Benzene derivatives. J. Am. Chem. Soc. 59:96–103.10.1021/ja01280a022Search in Google Scholar

Hill, C.A.S., Hillier, J.G. (1999) Studies of the reaction of carboxylic acid anhydrides with wood. Experimental determination and modeling of kinetic profiles. Phys. Chem. Chem. Phys. 1:1569–1576.10.1039/a809830aSearch in Google Scholar

Hill, C.A.S., Jones, D. (1996a) Dimensional changes in Corsican Pine Sapwood due to chemical modification with linear chain anhydrides. Holzforschung 50:457–462.10.1515/HF.1999.045Search in Google Scholar

Hill, C.A.S., Jones, D. (1996b) A chemical kinetics study of the propionic anhydride modification of Corsican Pin. (1) Determination of activation energies. J. Wood Chem. Technol. 16:235–247.10.1080/02773819608545806Search in Google Scholar

Hill, C.A.S., Jones, D. (1999) The dimensional stabilisation of Corsican Pine Sapwood by reaction with carboxylic acid anhydrides. Holzforschung 53:267–271.10.1515/HF.1999.045Search in Google Scholar

Hill, C.A.S., Papadopoulos, A.N., Payne, D. (2004) Chemical modification employed as a means of probing the cell-wall micropore of pine sapwood. Wood Sci. Technol. 37:475–488.10.1007/s00226-003-0193-5Search in Google Scholar

Ishii, Y., Nakano, T. (1997) Oxidation catalytic system and oxidation process using the same. Daicel Chemical Industries Ltd., US5958821 A:24.Search in Google Scholar

Ishii, Y., Sakaguchi, S. (1999) A new strategy for alkane oxidation with O₂ using N-hydroxyphthalimide (NHPI) as a radical catalyst. Catal. Surv. Jpn. 3:27–35.10.1023/A:1019059315516Search in Google Scholar

Jaffé, H.H. (1953) A reexamination of the Hammett equation. Chem. Rev. 53:191–261.10.1021/cr60165a003Search in Google Scholar

Jebrane, M., Heinmaa, I. (2015) Covalent fixation of boron in wood through transesterification with vinyl ester of carboxyphenylboronic acid. Holzforschung 70:577–583.10.1515/hf-2015-0118Search in Google Scholar

Kaldun, C., Dahle, S., Maus-Friedrichs, W., Namyslo, J.C., Kaufmann, D.E. (2016) Chemical improvement of surfaces. Part 4: significantly enhanced hydrophobicity of wood by covalent modification with p-silyl-functionalized benzoates. Holzforschung 70:411–419.10.1515/hf-2015-0036Search in Google Scholar

Keplinger, T., Cabane, E., Chanana, M., Hass, P., Merk, V., Gierlinger, N., Burgert, I. (2015) A versatile strategy for grafting polymers to cell walls. Acta Biomat. 11:256–263.10.1016/j.actbio.2014.09.016Search in Google Scholar

Kiryanov, A.A., Seed, A.J., Sampson, P. (2001) Synthesis and stability of 2-(1,1-difluoroalkyl)thiophenes and related 1,1-difluoroalkylbenzenes: fluorinated building block for liquid crystal synthesis. Tetrahedron 57:5757–5767.10.1016/S0040-4020(01)00519-1Search in Google Scholar

Li, J.-Z., Furuno, T., Katoh, S., Uehara, T. (2000) Chemical modification of wood by anhydrides without solvents or catalysts. J. Wood Sci. 46:215–221.10.1007/BF00776452Search in Google Scholar

Li, J.-Z., Furuno, T., Katoh, S., Uehara, T. (2001a) Wood propionylation in the presence of catalysts. Wood Fiber Sci. 33:255–263.Search in Google Scholar

Li, J.-Z., Furuno, T., Katoh, S. (2001b) Preparation and properties of acetylated and propionylated wood-silicate composites. Holzforschung 55:93–96.10.1515/HFSG.2001.93Search in Google Scholar

Liptáková, E., und Kúdela, J. (1994) Analysis of the wood-wetting process. Holzforschung 48:139–144.10.1515/hfsg.1994.48.2.139Search in Google Scholar

Mohammed-Ziegler, I., Marosi, G., Matkó, S., Hórvölgyi, Z., Tóth, A. (2003) Silylation of wood for potential protection against biodegradation. An ATR-FTIR, ESCA and contact angle study. Polym. Adv. Technol. 14:790–795.10.1002/pat.396Search in Google Scholar

Mohtar, M.A., Hamid, N.H., Sahri, M.H. (2014) Effect of linear chain carboxylic acid anhydrides on physical and mechanical properties of rubber (Hevea brasiliensis), acacia, (Acacia spp.), and oil palm (Tinnera spp.). Woods. J. Composites 2014:1–10.10.1155/2014/983634Search in Google Scholar

Morrow, N.R.C.P. (1975) The effects of surface roughness on contact angle with special reference to petroleum recovery. J. Can. Petrol. Technol. 14:42–53.10.2118/75-04-04Search in Google Scholar

Nakagami, T., Yokota, T. (1975) Esterification of wood with unsaturated carboxylic acids. II: reaction conditions of esterification and properties of the prepared esters of wood. Bull. Kyoto Univers. Forests 47:178–183.Search in Google Scholar

Nakagami, T., Yokota, T. (1979) Grafting of styrene onto methacrylated woods. Bull. Kyoto Univers. Forests 51:274–284.Search in Google Scholar

Nakagami, T., Amimoto, H., Yokota, T. (1974) Esterification of wood with unsaturated carboxylic acids. I: preparation of several wood-esters by the TFAA method. Bull. Kyoto Univers. Forests 46:217–224.Search in Google Scholar

Nakano, T. (1994) Mechanism of thermoplasticity for chemically-modified wood. Holzforschung 48:318–324.10.1515/hfsg.1994.48.4.318Search in Google Scholar

Namyslo, J.C., Kaufmann, D.E. (2009) Chemical improvement of surfaces. Part 1: novel functional modification of wood with covalently bound organoboron compounds. Holzforschung 63:627–632.10.1515/HF.2009.112Search in Google Scholar

Namyslo, J.C., Kaufmann, D.E., Mai, C.M., Militz, H. (2015) Chemical improvement of surfaces. Part 3: bioresistance of covalently functionalized wood bearing boronate-, silyl-, and amino-substituted benzoyl derivatives. Holzforschung 69:595–601.10.1515/hf-2014-0086Search in Google Scholar

Papadopoulos, A.N., Hill, C.A.S. (2002) The biological effectiveness of wood modified with linear chain carboxylic acid anhydrides against Coniophora puteana. Holz Roh Werkst. 60:329–332.10.1007/s00107-002-0327-8Search in Google Scholar

Papadopoulos, A.N., Hill, C.A.S. (2003) The sorption of water vapour by anhydride modified softwood. Wood Sci. Technol. 37:221–231.10.1007/s00226-003-0192-6Search in Google Scholar

Papadopoulos, A.N., Pougioula, G. (2010) Mechanical behaviour of pine wood chemically modified with a homologous series of linear chain carboxylic acid anhydrides. Biores. Technol. 101:6147–6150.10.1016/j.biortech.2010.02.079Search in Google Scholar

Papadopoulos, A.N., Avtzis, D.N., Avtzis, N.D. (2008a) The biological effectiveness of wood modified with linear chain carboxylic acid anhydrides against the subterranean termites Reticulitermes flavipes. Holz Roh Werkst. 66:249–252.10.1007/s00107-008-0252-6Search in Google Scholar

Papadopoulos, A.N., Duquesnoys, P., Cragg, S.M., Pitman, A.J. (2008b) The resistance of wood modified with linear chain carboxylic acid anhydrides to attack by the marine wood borer Limnoria quadripunctata Holthius. Int. Biodet. Biodeg. 61:199–202.10.1016/j.ibiod.2007.11.004Search in Google Scholar

Papadopoulos, A.N., Pfeffer, A., Militz, H. (2011) Durability of pine wood modified with a series of linear chain carboxylic acid anhydrides against soft rot fungi. Wood Res. 56:147–156.Search in Google Scholar

Risi, J., Arseneau, D.F. (1957) Dimensional stabilization of wood: Part II. Crotonylation and crotylation. Forest Prod. J. 7:245–246.Search in Google Scholar

Rodrìguez-Valverde, M.A., Cabrerizo-Vilchez, M.A., Rosales- López, P., Páez-Duenas, A., Hidalgo-Álvarez, R. (2002) Contact angle measurements on two (wood and stone) non-ideal surfaces. Colloids Surf. A: Physicochem. Eng. Aspects 206:485–495.10.1016/S0927-7757(02)00054-7Search in Google Scholar

Shiraishi, N., Matsunaga, T., Yokota, T. (1979) Thermal softening and melting of esterified wood prepared in an N₂O₄–DMF cellulose solvent medium. J. Appl. Polym. Sci. 24:2361–2368.10.1002/app.1979.070241204Search in Google Scholar

Thiebaud, S., Borredon, M.E. (1995) Solvent-free wood esterification with fatty acid chlorides. Biores. Technol. 52:169–173.10.1016/0960-8524(95)00018-ASearch in Google Scholar

Thiebaud, S., Borredon, M.E., Baziard, G., Senocq, F. (1997) Properties of wood esterified by fatty-acid chlorides. Biores. Technol. 59:103–107.10.1016/S0960-8524(96)00160-5Search in Google Scholar

Shorter, J. (1985) Die Hammett-Gleichung – und was daraus in fünfzig Jahren wurde. Chem. unserer Zeit 19:197–208.10.1002/ciuz.19850190604Search in Google Scholar

Stamm, A.J., Tarkow, H. (1947) Dimensional stabilization of wood. J. Phys. Colloid Sci. 51:493–505.10.1021/j150452a016Search in Google Scholar PubMed

Verma, P., Junga, U., Militz, M., Mai, C. (2009) Protection mechanisms of DMDHEU treated wood agaings white and brown rot fungi. Holzforschung 63:371–378.10.1515/HF.2009.051Search in Google Scholar

Wålinder, M.E.P., Gardner, D.J. (2002) Factors influencing the determination of wood contact angles and wettability – extractives contamination, wicking and bulk sorption effects. Contact Angle Wettab. Adh. 2:215–238.Search in Google Scholar

Received: 2019-08-03

Accepted: 2019-10-21

Published Online: 2019-12-09

Published in Print: 2020-07-28

You are currently not able to access this content.

Articles in the same Issue

https://doi.org/10.1515/hf-2019-0196

Keywords for this article

alkylation; attenuated total reflection IR (ATR-IR); contact angle (CA); covalent fixation; esterification; hydrophobization; quantity of covalently bonded organomaterial (QCO)