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Synthesis of polyesteramides: poly(ethylene adipate amide) and poly(ethylene succinate amide) and their application as corrosion inhibitors in paint formulations

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Abstract

Aliphatic polyesters based on adipic or succinic acid were synthesized by polycondensation reaction to produce poly(ethylene adipate) (PEA) and poly(ethylene succinate) (PES), respectively. The prepared polyesters (PEA and PES) were modified with monoethanol amine to produce polyesteramides, namely polyethylene adipate amide (PEAA) and polyethylene succinate amide (PESA). Full characterization of PEA, PES, PEAA and PESA was achieved using thermal, spectroscopic, and gel permeation chromatography analyses. The prepared aliphatic polyesters (PEA and PES) and polyesteramides (PEAA and PESA) were evaluated as corrosion inhibitors in paint formulations. Two groups of paints were prepared with 24 paint formulations based on medium oil alkyd resin, talc, titanium dioxide, drier and the prepared polymers with different types and concentrations. All the formulations are free from any inorganic anticorrosive pigments. PEA and PEAA were incorporated in Group I formulations. Paint formulations that contain PEA are six formulations F1A, F2A, F3A, F4A, F5A and F6A in addition to F1Aa, F2Aa, F3Aa, F4Aa, F5Aa and F6Aa based on PEAA with different concentrations 0.5%, 1.5%, 2.5%, 3.5%,4.5% and 5.5%, respectively. Group II formulations contain twelve other prepared formulations F1S, F2S, F3S, F4S, F5S and F6S based on PES, in addition to F1Sa, F2Sa, F3Sa, F4Sa, F5Sa and F6Sa based on PESA with the same series of concentrations. Physical, mechanical, and chemical properties of the coated films were determined. Corrosion tests in addition to surface analysis by a scanning electron microscope were performed to study the protection efficiency of such coats on steel. It was found that the synthesized polyesteramides can protect steel from corrosion successfully in 3.5% NaCl solution depending on their adsorption on the steel surface. The extent of steel protection coated with PESA formulations was slightly higher than PEAA.

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References

  1. Clarinval, A-M, Halleux, J, “Classification of Biodegradable Polymers.” In: Smith, R (ed.) Biodegradable Polymers for Industrial Applications, p. 3. Woodhead Publishing Limited, Cambridge (2005)

    Chapter  Google Scholar 

  2. Jérôme, C, Lecomte, P, “Recent Advances in the Synthesis of Aliphatic Polyesters by Ring-Opening Polymerization.” Adv. Drug Deliv. Rev., 60 1056–1076 (2008)

    Article  Google Scholar 

  3. Roumanet, P-J, Laflèche, F, Jarroux, N, Raoul, Y, Claude, S, Guégan, P, “Novel Aliphatic Polyesters From an Oleic Acid Based Monomer. Synthesis, Epoxidation, Cross-Linking and Biodegradation.” Eur. Polymer J., 49 813–822 (2013)

    Article  Google Scholar 

  4. Dhamaniya, S, Jacob, J, “Synthesis and Characterization of Polyesters Based on Tartaric Acid Derivatives.” Polymer, 51 5392–5399 (2010)

    Article  Google Scholar 

  5. Luckachan, GE, Pillai, CKS, “Random Multiblock Poly(Ester Amide)s Containing Poly(l-Lactide) and Cyclo Aliphatic Amide Segments: Synthesis and Biodegradation Studies.” J. Polym. Sci., Part A: Polym. Chem., 44 3250 (2006)

    Article  Google Scholar 

  6. van der Shuur, M, Gaymans, RJ, “Segmented Block Copolymers Based on Poly(Propylene Oxide) and Mono Disperse Polyamide-6,T Segments.” J. Polym. Sci., Part A: Polym. Chem., 44 4769 (2006)

    Article  Google Scholar 

  7. Deep, P, Sona, C, Jayakannan, M, “Synthesis and Investigation of the Effect of Nematic Phases on the Glass-Transition Behavior of Novel Cyclo Aliphatic Liquid-Crystalline Poly(Ester Amide)s.” J. Polym. Sci., Part A: Polym. Chem., 44 5557 (2006)

    Article  Google Scholar 

  8. Harashina, H, Nakane, T, Itoh, T, “Synthesis of Poly(Ester Amide)s by the Melt Polycondensation of Semiaromatic Polyesters with Ethanolamine and Their Characterization.” J. Polym. Sci., Part A: Polym. Chem., 45 2184–2193 (2007)

    Article  Google Scholar 

  9. Okada, M, “Chemical Synthesis of Biodegradable Polymers.” Prog. Polym. Sci., 27 87–133 (2000)

    Article  Google Scholar 

  10. Lips, PAM, Dijkstra, PJ, Biodegradable Polymers for Industrial Applications, Chap. 5, pp. 109–139. CRC Press, Boca Raton (2005)

    Google Scholar 

  11. Aqeel, S, Abd El-Wahab, H, Mahdy, A, Abd El-Hai, F, Abd El-Fattah, M, “New Modified Polyesteramide Resin for Industrial Applications.” Prog. Org. Coat., 68 219–224 (2010)

    Article  Google Scholar 

  12. More, AP, Mhaske, ST, “Anticorrosive Coating of Polyesteramide Resin by Functionalized ZnO-Al2O3-Fly Ash Composite and Functionalized Multiwalled Carbon Nanotubes.” Prog. Org. Coat., 99 240–250 (2016)

    Article  Google Scholar 

  13. Mohamed, HA, Abdel Rehim, M, “Surface Active Hyperbranched Polyamide-Ester as a Corrosion Inhibitor in Both Neutral and Acidic Media.” Anti Corros. Methods Mater., 62 (2) 95–102 (2015)

    Article  Google Scholar 

  14. Burns, RM, Bradly, WW, Protective Coating for Metal, 3rd ed., p. 674. Renhold Publishing Corporation, NY (1984)

    Google Scholar 

  15. Gomaa, AZ, Gad, H, J. Oil Color Chem. Assoc.: JOCCA, 71 (2) 50–54 (1988)

    Google Scholar 

  16. Mohamed, HA, Farag, AA, Badran, BM, “Preparation and Emulsification of New Steel Corrosion Inhibitors.” Eurasian Chem. Technol. J., 8 225–235 (2006)

    Google Scholar 

  17. Ramadan, AM, Gomaa, AZ, Eur. Coat. J., 11 740–749 (1992)

    Google Scholar 

  18. Abdel-Hai, F, Abdel-Wahab Mohamed, A, Eur. Coat. J., 3 (4) 28–33 (2004)

    Google Scholar 

  19. Mohamed, HA, Badrana, BM, Rabie, AM, Morsi, SMM, “Synthesis and Characterization of Aqueous (Polyurethane/Aromaticpolyamide Sulfone) Copolymer Dispersions from Castor Oil.” Prog. Org. Coat., 77 (6) 965–974 (2014)

    Article  Google Scholar 

  20. Licis, IJ, “Pollution Prevention Possibilities for Small and Medium-Sized Industries.” Environ. Prog., 14 (4) 224–231 (1995)

    Article  Google Scholar 

  21. Badran, BM, Mohamed, HA, Aglan, HA, “Effect of Different Polymers on the Efficiency of Methylamine Adduct as Corrosion Inhibitors for Surface Coatings.” J. Appl. Polym. Sci., 85 879–885 (2002)

    Article  Google Scholar 

  22. Hariharaputhran, R, Subramanian, A, Anthony, AA, “Influence of Nitrones on Corrosion Inhibition and Hydrogen Permeation Through Mild Steel in Acidic Solutions.” Anti Corros. Methods Mater., 46 (1) 35–39 (1999)

    Article  Google Scholar 

  23. Mohamed, HA, Badran, BM, “Pilot Plant Study of Water-Borne High Molecular Weight Amine Adduct as Corrosion Inhibitor in Emulsion Paints.” J. Appl. Polym. Sci., 115 174–182 (2010)

    Article  Google Scholar 

  24. Vasudevan, T, Muralidharan, B, Muralidharan, S, “Inhibition of Corrosion of Mild Steel in Acidic Solutions by Quarternary Salts of Pyridinium Bases.” Anti Corros. Methods Mater., 45 (2) 120–126 (1998)

    Article  Google Scholar 

  25. Mohamed, HA, “Eco-Friendly Zero VOC Anticorrosive Paints for Steel Protection.” J. Appl. Polym. Sci., 125 (3) 1790–1795 (2012)

    Article  Google Scholar 

  26. Ataei, S, Yahya, R, Gan, SN, “Coating Performances of Copolymers from a Novel Palm Oil Based Macromer and Methyl Methacrylate.” Pigm. Resin Technol., 41 (2) 112–121 (2012)

    Article  Google Scholar 

  27. Gast, LE, Schneider, WJ, Cowan, JC, “Polyester Amides from Linseed Oil for Protective Coatings.” J. Am. Oil Chem. Soc.: JAOCS, 43 (6) 418–421 (1966)

    Article  Google Scholar 

  28. Gast, LE, Schneider, WJ, Mc Manis, GE, Cowan, JC, “Polyesteramides from Linseed and Soybean Oils for Protective Coatings: Diisocyanate-Modified Polymers.” J. Am. Chem. Soc.: JAOCS, 46 (7) 360–364 (1969)

    Google Scholar 

  29. Economy, J, “Liquid Crystalline Aromatic Polyesters.” J. Macromol. Sci. Part A Pure Appl. Chem., 21 1705–1724 (1984)

    Article  Google Scholar 

  30. Pal, RR, Patil, PS, Salunkhe, MM, Maldar, NN, Wadgaonkar, PP, “Synthesis, Characterization and Constitutional Isomerism Study of New Aromatic Polyamides Containing Pendant Groups Based on Asymmetrically Substituted Meta-Phenylene Diamines.” Eur. Polymer J., 45 953–959 (2009)

    Article  Google Scholar 

  31. Sheng, S, Li, T, Jiang, J, He, W, Song, C, “Synthesis and Properties of Novel Polyamides Containing Sulfone-Ether Linkages and Xanthene Cardo Groups.” Polym. Int., 59 1014–1020 (2010)

    Article  Google Scholar 

  32. Liu, YJ, Pei, XL, Sheng, SR, Yang, F, Liu, XL, Song, CS, “Synthesis and Characterization of Novel Aromatic Poly(Ester Amide)s Containing Pendant Trifluoromethylphenoxy Groups.” J. Appl. Polym. Sci., 125 3904–3912 (2012)

    Article  Google Scholar 

  33. Zhu, D, van Ooij, WJ, “Corrosion Protection of Metals by Water-Based Silane Mixtures of Bis-[trimethoxysilylpropyl]amine and Vinyltriacetoxysilane.” Prog. Org. Coat., 49 (1) 42–53 (2004)

    Article  Google Scholar 

  34. Malik, VP, Neemla, KD, Kumar, V, “Sulphonates as Rust Inhibitors.” Anti Corros. Methods Mater., 33 (7) 12–18 (1986)

    Article  Google Scholar 

  35. Bisht, RP, Sivasankaran, GA, Jayaraman, A, Bhatia, VK, “Effect of Corrosion Inhibitor on the Performance of Extreme Pressure Additive.” Anti Corros. Methods Mater., 38 (8) 4–6 (1991)

    Article  Google Scholar 

  36. Yurt, A, Mihrican, Y, “Quantitative Relationships Between the Structure of Some Thiol Compounds and Their Inhibition Efficiencies.” Anti Corros. Methods Mater., 55 (4) 195–203 (2008)

    Article  Google Scholar 

  37. Bereket, G, Gülec, M, Yurt, A, “Inhibition Efficiencies of Some Organic Compounds on the Corrosion of Zinc in Alkaline Media.” Anti Corros. Methods Mater., 53 (1) 52–56 (2006)

    Article  Google Scholar 

  38. Olivares, GZ, Gayosso, MJ, Mendoza, JL, “Corrosion Inhibitors Performance for Mild Steel in CO2 Containing Solutions.” Mater. Corros., 58 (6) 427–437 (2007)

    Article  Google Scholar 

  39. Mohamed, HA, “Environmentally Friendly Paints, Chapter 6.” In: Sarrica, SM (ed.) Paints Types, Components and Application, pp. 127–139. Nova Publisher, USA (2011)

    Google Scholar 

  40. Mohamed, HA, Badran, BM, Farag, AA, “Friendly to Environment Heterocyclic Adducts as Corrosion Inhibitors for Steel in Paints.” J. Appl. Polym. Sci., 117 (3) 1270–1278 (2010)

    Google Scholar 

  41. Alsabagh, AM, Migahed, MA, Awad, HS, “Reactivity of Polyester Aliphatic Amine Surfactants as Corrosion Inhibitors for Carbon Steel in Formation Water (Deep Well Water).” Corros. Sci., 48 813–828 (2006)

    Article  Google Scholar 

Download references

Funding

Authors would like to express their appreciations to National Research Center (NRC), Egypt, that funded this research.

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Authors and Affiliations

  1. Polymers and Pigment Department, National Research Centre, Dokki, Giza, Egypt

    Heba A. Mohamed, Yasser Assem & Rana Said

  2. Chemistry Department, Faculty of Science, Zagazig University, Zagazig, Egypt

    Ahmed M. El-Masry

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  1. Heba A. Mohamed
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  2. Yasser Assem
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  3. Rana Said
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Correspondence to Heba A. Mohamed.

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Mohamed, H.A., Assem, Y., Said, R. et al. Synthesis of polyesteramides: poly(ethylene adipate amide) and poly(ethylene succinate amide) and their application as corrosion inhibitors in paint formulations. J Coat Technol Res 15, 967–981 (2018). https://doi.org/10.1007/s11998-017-0027-2

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