Abstract
Alkyl phosphonic acids are amphiphilic structures consisting of non-polar organic hydrophobic groups and anionic inorganic hydrophilic groups, which makes them be able to behave as surfactants as well as smart corrosion inhibitors. A simple and high yield (up to 87%) pathway for synthesizing decyl phosphonic acid (DPA) is described. 1H and 13C-NMR) as well as FTIR spectroscopy were used to characterize chemical structures and purity of the obtained product. Thermal properties and crystal structure of DPA were investigated using differential scanning calorimetry analysis (DSC) and thermogravimetric analysis (TGA). The stability of DPA in Oil-in-Water (O/W) and Water-in-Oil (W/O) emulsions was improved in the presence of ammonium persulfate (APS), which allowed us to measure their specific characteristics such as particle size and zeta potential (ξ) of micelles. Both emulsions were used for synthesizing polyaniline (PANI) by emulsion polymerization. Wettability of DPA on the mild steel surface was examined using contact angle measurements. Moreover, corrosion-inhibition properties studied by using electrochemical impedance spectroscopy (EIS) technique and salt spray test results revealed that DPA can be an efficient ingredient for anti-corrosion coating.
Similar content being viewed by others
References
A. Kalir and H. H. Kalir, In PATAI’S Chemistry of Functional Groups, Wiley (2009).
K. Chruszcz, M. Baranska, K. Czarniecki and L. M. Proniewicz, J. Mol. Struct., 651, 729 (2003).
A. F. O. Regina Luschtinetz, Surf. Sci., 602, 1347 (2008).
R. Quiñones, A. Raman and E. S. Gawalt, Thin Solid Films, 516, 8774 (2008).
T. Vallant, H. Brunner, U. Mayer and H. Hoffmann, Langmuir, 14, 5826 (1998).
I. Maege, E. Jaehne, A. Henke, H.-J.P. Adler, C. Bram, C. Jung and M. Stratmann, Macromol. Symp., 126, 7 (1998).
J. J. Hickman, D. Ofer, P. E. Laibinis, G. M. Whitesides and M. Wrighton, Science, 252, 688 (1991).
C. Bressy-Brondino, B. Boutevin, Y. Hervaud and M. Gaboyard, J. Appl. Polym. Sci., 83, 2277 (2002).
I. Maege, E. Jaehne, A. Henke, H.-J.P. Adler, C. Bram, C. Jung and M. Stratmann, Prog. Org. Coat., 34, 1 (1997).
A. Badia, R. B. Lennox and L. Reven, Acc. Chem. Res., 33, 475 (2000).
T. Nakamoto, M. Katada, K. Endo and H. Sano, Polyhedron, 17, 3507 (1998).
S. Valiyaveettil, V. Enkelmann and K. Müllen, J. Chem. Soc. Chem. Commun., 18, 2097 (1994).
T. T. Foster, M. R. Alexander, G. J. Leggett and E. McAlpine, Langmuir, 22, 9254 (2006).
M. Green and R. F. Hudson, J. Chem. Soc., 3129 (1958).
G. M. Kosolapoff, Organic phosphorus compounds, Vol. 4; Wiley-Interscience, New York (1972).
G. M. Kosolapoff, Organic Phosphorus Compounds, Vol. 7, 7th Ed., Maier, L., Ed., Wiley, New York (1976).
P. Fiurasek and L. Reven, Langmuir, 23, 2857 (2007).
Y. Sahoo, H. Pizem, T. Fried, D. Golodnitsky, L. Burstein, C. N. Sukenik and G. Markovich, Langmuir, 17, 7907 (2001).
J. K. Thottathil, Process for preparing phosphonic acids, Patent US No. 4670193, June 2 (1987).
H. S.O. Chan, S. C. Ng and P. K. H. Ho, Macromolecules, 27, 2159 (1994).
D. Boczula, A. Caly, D. Dobrzynska, J. Janczak and J. Zon, J. Mol. Struct., 1007, 220 (2012).
F. X. Perrin, T. A. Phan and D.L. Nguyen, Eur. Polym. J., 66, 253 (2015).
F. X. Perrin, T. A. Phan and D. L. Nguyen, J. Polym. Sci. Part Polym. Chem., 53, 1606 (2015).
D. L. Allara and R.G. Nuzzo, Langmuir, 1, 45 (1985).
R. G. Snyder, H. L. Strauss and C. A. Elliger, J. Phys. Chem., 86, 5145 (1982).
R. Helmy and A. Y. Fadeev, Langmuir, 18, 8924 (2002).
P. C. Schulz, M. Abrameto, J. E. Puig, F. A. Soltero-Martínez and A. Gonzalez-Alvarez, Langmuir, 12, 3082 (1996).
S. C. D’Andre and A. Y. Fadeev, Langmuir, 19, 7904 (2003).
C. C. Schulz, E-Gnos., 1, 14 (2003).
T. Hoffmann, P. Friedel, C. Harnisch, L. Häuβler and D. Pospiech, J. Anal. Appl. Pyrolysis, 96, 43 (2012).
B. Lafitte and P. Jannasch, J. Polym. Sci. Part Polym. Chem., 43, 273 (2005).
D. D. Jiang, Q. Yao, M. A. McKinney and C. A. Wilkie, Polym. Degrad. Stab., 63, 423 (1999).
P. Walde, M. Wessicken, U. Rädler, N. Berclaz, K. Conde-Frieboes and P. L. Luisi, J. Phys. Chem. B, 101, 7390 (1997).
E. B. Leodidis and T. A. Hatton, Langmuir, 5, 741 (1989).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Phan, TA., Perrin, FX. & Nguyen-Dinh, L. Synthesis and characterization of decyl phosphonic acid, applications in emulsion polymerization and anti-corrosion coating. Korean J. Chem. Eng. 35, 1365–1372 (2018). https://doi.org/10.1007/s11814-018-0041-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11814-018-0041-9