Synthesis and characterization of decyl phosphonic acid, applications in emulsion polymerization and anti-corrosion coating

The-Anh Phan; François-Xavier Perrin; Lam Nguyen-Dinh

Korean Journal of Chemical Engineering, Vol.35, No.6, 1365-1372, June, 2018

DOI10.1007/s11814-018-0041-9 Export Citation

Synthesis and characterization of decyl phosphonic acid, applications in emulsion polymerization and anti-corrosion coating

The-Anh Phan, François-Xavier Perrin¹, and Lam Nguyen-Dinh^†

The University of Danang, University of Science and Technology, Danang, Viet Nam, Vietnam
¹Laboratoire MAPIEM EA 4323, SeaTech-Ecole d’ingénieurs, Université de Toulon, La Garde Cedex, France

E-mail:

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 (ζ) 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.

Keywords:Surfactant;Oil-in-water Emulsion;Water-in-oil Emulsion;Polyaniline

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Allara DL, Nuzzo RG, Langmuir, 1, 45 (1985)
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Schulz PC, Abrameto M, Puig JE, Solteromartinez FA, Gonzalezalvarez A, Langmuir, 12(12), 3082 (1996)
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Jiang DD, Yao Q, McKinney MA, Wilkie CA, Polym. Degrad. Stabil., 63, 423 (1999)
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[Referenced By]

[1] Kalir A, Kalir HH, In PATAI’S Chemistry of Functional Groups, Wiley (2009).

[2] Chruszcz K, Baranska M, Czarniecki K, Proniewicz LM, J. Mol. Struct., 651, 729 (2003)

[3] Luschtinetz AFOR, Surf. Sci., 602, 1347 (2008)

[4] Quinones R, Raman A, Gawalt ES, Thin Solid Films, 516(23), 8774 (2008)

[5] Vallant T, Brunner H, Mayer U, Hoffmann H, Langmuir, 14(20), 5826 (1998)

[6] Maege I, Jaehne E, Henke A, Adler HJP, Bram C, Jung C, Stratmann M, Macromol. Symp., 126, 7 (1998)

[7] Hickman JJ, Ofer D, Laibinis PE, Whitesides GM, Wrighton M, Science, 252, 688 (1991)

[8] Bressy-Brondino C, Boutevin B, Hervaud Y, Gaboyard M, J. Appl. Polym. Sci., 83(11), 2277 (2002)

[9] Maege I, Jaehne E, Henke A, Adler HJP, Bram C, Jung C, Stratmann M, Prog. Org. Coat., 34, 1 (1997)

[10] Badia A, Lennox RB, Reven L, Accounts Chem. Res., 33, 475 (2000)

[11] Nakamoto T, Katada M, Endo K, Sano H, Polyhedron, 17, 3507 (1998)

[12] Valiyaveettil S, Enkelmann V, Mullen K, J. Chem. Soc. Chem. Commun., 18, 2097 (1994)

[13] Foster TT, Alexander MR, Leggett GJ, McAlpine E, Langmuir, 22(22), 9254 (2006)

[14] Green M, Hudson RF, J. Chem. Soc., 3129 (1958).

[15] Kosolapoff GM, Organic phosphorus compounds, Vol. 4; Wiley-Interscience, New York (1972).

[16] Kosolapoff GM, Organic Phosphorus Compounds, Vol. 7, 7th Ed., Maier, L., Ed., Wiley, New York (1976).

[17] Fiurasek P, Reven L, Langmuir, 23(5), 2857 (2007)

[18] Sahoo Y, Pizem H, Fried T, Golodnitsky D, Burstein L, Sukenik CN, Markovich G, Langmuir, 17(25), 7907 (2001)

[19] Thottathil JK, Process for preparing phosphonic acids, Patent US No. 4670193, June 2 (1987).

[20] Chan HS, Ng SC, Ho PK, Macromolecules, 27(8), 2159 (1994)

[21] Boczula D, Cały A, Dobrzynska D, Janczak J, Zon J, J. Mol. Struct., 1007, 220 (2012)

[22] Perrin FX, Phan TA, Nguyen DL, Eur. Polym. J., 66, 253 (2015)

[23] Perrin FX, Phan TA, Nguyen DL, J. Polym. Sci. A: Polym. Chem., 53(13), 1606 (2015)

[24] Allara DL, Nuzzo RG, Langmuir, 1, 45 (1985)

[25] Snyder RG, Strauss HL, Elliger CA, J. Phys. Chem., 86, 5145 (1982)

[26] Helmy R, Fadeev AY, Langmuir, 18(23), 8924 (2002)

[27] Schulz PC, Abrameto M, Puig JE, Solteromartinez FA, Gonzalezalvarez A, Langmuir, 12(12), 3082 (1996)

[28] D'Andrea SC, Fadeev AY, Langmuir, 19(19), 7904 (2003)

[29] Schulz CC, E-Gnos., 1, 14 (2003)

[30] Hoffmann T, Friedel P, Harnisch C, Haußler L, Pospiech D, J. Anal. Appl. Pyrolysis, 96, 43 (2012)

[31] Lafitte B, Jannasch P, J. Polym. Sci. A: Polym. Chem., 43(2), 273 (2005)

[32] Jiang DD, Yao Q, McKinney MA, Wilkie CA, Polym. Degrad. Stabil., 63, 423 (1999)

[33] Walde P, Wessicken M, Radler U, Berclaz N, Condefrieboes K, Luisi PL, J. Phys. Chem. B, 101(38), 7390 (1997)

[34] Leodidis EB, Hatton TA, Langmuir, 5, 741 (1989)