journal article·2020-11-19Open access

Corrosion Resistance of Mild Steel Coated with Phthalimide-Functionalized Polybenzoxazines

Kamal I. Aly, Abdulsalam Mahdy, Mohamed A. Hegazy, Nayef S. Al-Muaikel, Shiao-Wei Kuo, Mohamed Gamal Mohamed

Coatings· Volume 10· Issue 11

Abstract

Herein, we synthesized two new phthalimide-functionalized benzoxazine monomers, pPP-BZ and oPP-BZ, through Mannich reactions of 2-(4-hydroxyphenyl)isoindoline-1,3-dione (pPP) and 2-(2-hydroxyphenyl)isoindoline-1,3-dione (oPP), respectively, with p-toluidine and paraformaldehyde. The structures of these two monomers were confirmed using Fourier transform infrared (FTIR) and nuclear magnetic resonance spectroscopy. We used differential scanning calorimetry, FTIR spectroscopy, and thermogravimetric analysis to study the polymerization behavior and thermal stability of the monomers and their corresponding polybenzoxazines. Poly(pPP-BZ) and poly(oPP-BZ) were formed on mild steel (MS) through spin-coating and subsequent thermal curing polymerization. We used various corrosion testing methods to examine the effect of the curing temperature on the corrosion resistance of the coated MS samples in 3.5 wt.% aqueous solution of NaCl. Among our tested systems, the corrosion rate reached a low of 2.78 µm·Y−1 for the MS coated with poly(pPP-BZ)180 (i.e., the coating that had been cured at 180 °C); this value is much lower than that (4.8 µm·Y−1) reported for a maleimide-based benzoxazine compound (MI-Bz)/33 wt.% ACAT (amine-capped aniline trimer) blend. Thus, the incorporation of the imide functional group into the PBZ coatings is an effective strategy for affording high-performance corrosion resistance.
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Research context

OpenAlex topics: Epoxy Resin Curing Processes · Synthesis and properties of polymers · Injection Molding Process and Properties

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Polymer Research Laboratory, Chemistry Department, Faculty of Science, Assiut University, Assiut 71516, Egypt

Chemistry Department, Faculty of Education & Science, Rada’a Al-Baydha University, Al-Baydha 38018, Yemen

Petrochemicals Department, Egyptian Petroleum Research Institute (EPRI), Nasr City, Cairo 11727, Egypt

Chemistry Department, College of Science, Al-Jouf University, Skaka 72388, Al-Jouf, Saudi Arabia

Department of Materials and Optoelectronic Science, Center of Crystal Research, National Sun Yat-Sen University, Kaohsiung 804, Taiwan

Funding

the Science and Technology Development Fund

References (69)

Show source-provided references
1. Electronic effects of asymmetric and meta-alkoxy substituents on the polymerization behavior of bis-benzoxazines10.1039/C9PY01641D ↗
2. Crown Ether-Functionalized Polybenzoxazine for Metal Ion Adsorption10.1021/acs.macromol.9b02519 ↗
3. Preparation, and characterization of carbon fiber reinforced polybenzoxazine and polybenzoxazole composites from the same precursor: Use of a smart, ortho-substituted and amide-co-imide functional matrix10.1016/j.compscitech.2020.108205 ↗
4. Bai, L., Ge, Y., and Bai, L. (2019). Boron and Nitrogen Co-Doped Porous Carbons Synthesized from Polybenzoxazines for High-Performance Supercapacitors. Coatings, 9.10.3390/coatings9100657 ↗
5. Synthesis and thermally induced structural transformation of phthalimide and nitrile-functionalized benzoxazine: Toward smart ortho-benzoxazine chemistry for low flammability thermosets10.1039/C8RA10009H ↗
6. A tetraphenylethylene-functionalized benzoxazine and copper (II) acetylacetonate form a high-performance polybenzoxazine10.1016/j.polymer.2020.122552 ↗
7. Bifunctional polybenzoxazine nanocomposites containing photo-crosslinkable coumarin units and pyrene units capable of dispersing single-walled carbon nanotubes10.1039/C5PY00035A ↗
8. Polymerization of an AB-Type Benzoxazine Monomer toward Different Polybenzoxazine Networks: When Diels–Alder Reaction Meets Benzoxazine Chemistry in a Single-Component Resin10.1021/acs.macromol.9b01581 ↗
9. Functional Silica and Carbon Nanocomposites Based on Polybenzoxazines10.1002/macp.201800306 ↗
10. Dai, J., Yang, S., Teng, N., Liu, Y., Liu, X., Zhu, J., and Zhao, J. (2018). Synthesis of Eugenol-Based Silicon-Containing Benzoxazines and Their Applications as Bio-Based Organic Coatings. Coatings, 8.10.3390/coatings8030088 ↗
11. Benzoxazine-Based Thermoset with Autonomous Self-Healing and Shape Recovery10.1021/acs.macromol.8b02137 ↗
12. Easily Processable Thermosets with Outstanding Performance via Smart Twisted Small-Molecule Benzoxazines10.1002/marc.201900625 ↗
13. Combining polybenzoxazines and polybutadienes via simultaneous inverse and direct vulcanization for flexible and recyclable thermosets by polysulfide dynamic bonding10.1039/C9PY01056D ↗
14. Modification of solventless synthesized benzoxazine resin by phthalonitrile group: An effective approach for enhancing thermal stability of polybenzoxazines10.1002/macp.201800291 ↗
15. Catalyst-Free and Low-Temperature Terpolymerization in a Single-Component Benzoxazine Resin Containing Both Norbornene and Acetylene Functionalities10.1021/acs.macromol.8b01558 ↗
16. Zhang, T., Bonnaud, L., Raquez, T.M., Poorteman, M., Olivier, M., and Dubois, P. (2020). Cerium Salts: An Efficient Curing Catalyst for Benzoxazine Based Coatings. Polymers, 12.10.3390/polym12020415 ↗
17. Pyrene-functionalized tetraphenylethylene polybenzoxazine for dispersing single-walled carbon nanotubes and energy storage10.1016/j.compscitech.2020.108360 ↗
18. Enhanced CO2 capture in nitrogen-enriched microporous carbons derived from Polybenzoxazines containing azobenzene and carboxylic acid units10.1007/s10965-020-02179-1 ↗
19. Bisbenzylidene cyclopentanone and cyclohexanone-functionalized polybenzoxazine nanocomposites: Synthesis, characterization, and use for corrosion protection on mild steel10.1016/j.mtcomm.2020.101418 ↗
20. Benzoxazine/Triphenylamine-Based Dendrimers Prepared through Facile One-Pot Mannich Condensations10.1002/marc.201700251 ↗
21. Crosslinking polyimides for membrane applications: A review10.1016/j.progpolymsci.2012.11.001 ↗
22. Mohamed, M.G., and Kuo, S.W. (2019). Functional polyimide/polyhedral oligomeric silsesquioxane nanocomposites. Polymers, 11.10.3390/polym11010026 ↗
23. Synthesis of sulfonic acid-containing polybenzoxazine for proton ex proton exchange membrane in direct methanol fuel cells10.1021/ma4020214 ↗
24. Performance improvement of polybenzoxazine by alloying with polyimide: Effect of preparation method on the properties10.1016/j.polymer.2005.03.096 ↗
25. Enhanced corrosion resistance of polybenzoxazine coatings by epoxy incorporation10.1039/C6RA02215D ↗
26. The determination of coating performance with impedance measurements-I. Coating polymer properties10.1016/0010-938X(93)90245-C ↗
27. Silane-functionalized polybenzoxazines: A superior corrosion resistant coating for steel plates10.1002/maco.201709587 ↗
28. Preparation of diamine-based polybenzoxazine coating for corrosion protection on mild steel10.1007/s10965-018-1683-3 ↗
29. Synthesis and characterization of aniline-dimer-based electroactive benzoxazine and its polymer10.1039/C7RA11349H ↗
30. Synthesis and electrochemical properties of electroactive aniline-dimer-based benzoxazines for advanced corrosion-resistant coatings10.1007/s10853-018-2113-y ↗
31. Crosslinked main-chain-type polybenzoxazine coatings for corrosion protection of mild steel10.1007/s11998-016-9902-5 ↗
32. Synthetic of Phthalimides via the reaction of phthalic anhydride with amines and evaluating of its biological and anticorrosion activity
33. A novel Schiff base-based cationic gemini surfactants: Synthesis and effect on corrosion inhibition of carbon steel in hydrochloric acid solution10.1016/j.corsci.2009.06.046 ↗
34. Nitrogen-Doped microporous carbons derived from azobenzene and nitrile-functionalized polybenzoxazines for CO2 uptake10.1016/j.mtcomm.2020.101111 ↗
35. Directly synthesized nitrogen-and-oxygen–doped microporous carbons derived from a bio-derived polybenzoxazine exhibiting high-performance supercapacitance and CO2 uptake10.1016/j.eurpolymj.2020.109954 ↗
36. Salicylaldehyde azine-functionalized polybenzoxazine: Synthesis, characterization, and its nanocomposites as coatings for inhibiting the mild steel corrosion10.1016/j.porgcoat.2019.105385 ↗
37. The evolution of poly (hydroxyamide amic acid) to poly (benzoxazole) via stepwise thermal cyclization: Structural changes and gas transport properties10.1016/j.polymer.2011.08.043 ↗
38. Ortho-Imide and Allyl Groups Effect on Highly Thermally Stable Polybenzoxazine/Double-Decker-Shaped Polyhedral Silsesquioxane Hybrids10.1021/acs.macromol.8b02207 ↗
39. An anomalous trade-off effect on the properties of smart ortho-functional benzoxazines10.1039/C5PY00031A ↗
40. Direct synthesis of poly (benzoxazine imide) from an ortho-benzoxazine: Its thermal conversion to highly cross-linked polybenzoxazole and blending with poly (4-vinylphenol)10.1039/C8PY00087E ↗
41. Takeichi, Preparation of Imide-modified Benzoxazines and Characterization of Cured Films10.2494/photopolymer.28.145 ↗
42. Multivalent photo-crosslinkable coumarin-containing polybenzoxazines exhibiting enhanced thermal and hydrophobic surface properties10.1039/C5RA27705A ↗
43. Multifunctional polybenzoxazine nanocomposites containing photoresponsive azobenzene units, catalytic carboxylic acid groups, and pyrene units capable of dispersing carbon nanotubes10.1039/C5RA07983G ↗
44. Supramolecular functionalized polybenzoxazines from azobenzene carboxylic acid/azobenzene pyridine complexes: Synthesis, surface properties, and specific interactions10.1039/C4RA15107K ↗
45. Study on the synergistic anticorrosion property of a fully bio-based polybenzoxazine copolymer resin10.1016/j.eurpolymj.2019.07.020 ↗
46. Synthesis and characterization of thermally curable guaiacol based poly (benzoxazine-urethane) coating for corrosion protection on mild steel10.1016/j.eurpolymj.2016.12.030 ↗
47. Reaction mechanism and synergistic anticorrosion property of reactive blends of maleimide-containing benzoxazine and amine-capped aniline trimer10.1039/C4PY00274A ↗
48. Chitosan-polypyrrole-SiO2 composite coatings with advanced anticorrosive properties10.1016/j.synthmet.2014.12.019 ↗
49. Conducting polyaniline–nano-TiO2 composites for smart corrosion resistant coatings10.1016/j.electacta.2008.08.069 ↗
50. The corrosion performance and adhesion properties of the epoxy coating applied on the steel substrates treated by cerium-based conversion coatings10.1016/j.corsci.2015.02.028 ↗
51. Correction: Synergistic effects of hydrophobicity and gas barrier properties on the anticorrosion property of PMMA nanocomposite coatings embedded with graphene nanosheets10.1039/C4PY90078B ↗
52. Influence of copper nanoparticles capped by cationic surfactant as modifier for steel anti-corrosion paints10.1016/j.ejpe.2013.11.009 ↗
53. Hydrophobic benzoxazine-cured epoxy coatings for corrosion protection10.1016/j.porgcoat.2013.03.013 ↗
54. Nanosilicon dioxide/o-phenylenediamine hybrid composite as a modifier for steel paints10.1016/j.porgcoat.2013.01.009 ↗
55. Polybenzoxazine/SiO2 nanocomposite coatings for corrosion protection of mild steel10.1016/j.corsci.2013.11.042 ↗
56. Effect of seawater biofilms on corrosion potential and oxygen reduction of stainless steel10.5006/1.3584936 ↗
57. Evaluation of the corrosion resistance of an epoxy-polyamide coating containing different ratios of micaceous iron oxide/Al pigments10.1016/j.corsci.2011.01.045 ↗
58. Smart synthesis of high-performance thermosets based on ortho-amide–imide functional benzoxazines10.3389/fmats.2015.00005 ↗
59. Relation between Corrosion Inhibition Efficiency of Polar Organic Compounds for Some Non-transition Metals and the HSAB Principle10.3323/jcorr1974.32.3_144 ↗
60. Corrosion protection of hydrophobic bisphenol A-based polybenzoxazine coatings on mild steel10.1039/C5RA22980D ↗
61. Kelly, R.G., Scully, J.R., Shoesmith, D., and Buchheit, R.G. (2002). Electrochemical Techniques in Corrosion Science and Engineering, CRC Press.10.1201/9780203909133 ↗
62. Preparation, and surface properties of novel low surface free energy fluorinated silane-functional polybenzoxazine films10.1021/la200073v ↗
63. Effect of N-substituents on the surface characteristics and hydrogen bonding network of polybenzoxazines10.1016/j.polymer.2011.01.009 ↗
64. 4,4′-(((1E,5E)-pentane-1,5-diylidene)bis(azanylylidene))bis(1-dodecylpyridin-1-ium) bromide as a novel corrosion inhibitor in an acidic solution (Part I)10.1016/j.msec.2020.110673 ↗
65. A corrosion-protective coating based on a solution-processable polymer-grafted graphene oxide nanocomposite10.1016/j.corsci.2015.05.056 ↗
66. Corrosion inhibition performance of a novel cationic surfactant for protection of carbon steel pipeline in acidic media10.20964/2018.07.53 ↗
67. The substituted 1, 3, 4-oxadiazoles: A new class of corrosion inhibitors of mild steel in acidic media10.1016/S0010-938X(99)00049-9 ↗
68. Thermal curing of para-phenylenediamine benzoxazine for barrier coating applications on 1050 aluminum alloys10.1016/j.porgcoat.2016.03.026 ↗
69. Henna leaves extract as a corrosion inhibitor in acrylic resin coating10.1016/j.porgcoat.2017.01.017 ↗