Abstract
The present work investigate the coating behaviors of a series of polybenzoxazines (PBZs) derived from N-phenyl pyrazolidine scaffold based bisphenol (PPBP) and long chain aliphatic amines. Initially, the prepared PPBP was verified for its non-toxicity in comparison with bisphenol-A. Subsequently, the PBZs prepared from PPBP displayed enhanced values of water contact angle (WCA) when coated over different substrates namely cotton fabric and mild steel. In specific, the poly(PPBP-dda) and poly(PPBP-oda) coated cotton fabrics delivered outstanding WCA values of 154.2° and 153.5°, respectively. Observations from SEM images suggest that poly(PPBP-dda), and poly(PPBP-oda) exhibit closely packed molecular arrangement contributing for rough surfaces due to presence of their long dodecyl(C12) and octadecyl(C18) chains, respectively. Subsequently the oil-water separation investigation using the poly(PPBP-dda) coated fabric delivered superior separation efficiency (98 %) and flux values [6330 L/(m2 h)]. At the same time, the mild steel specimens when coated with poly(PPBP-dda) was also found to be less aggressive towards corrosion in artificial sea-water showing 81% efficiency and charge transfer resistance (Rct) of 280 Ω cm–2. Further, screening of the PPBP monomer and corresponding polybenzoxazines exhibited good antibacterial activity. Thus, a new type of PPBP based PBZs prepared in present work can lead further development of various new non-toxic substrates to replace bis-phenol derivatives.
REFERENCES
Hatsuo, Ishida and Tarek, Agag, Handbook of Benzoxazine Resins, Amsterdam: Elsevier, 2011. https://doi.org/10.1016/C2010-0-66598-9
Okada, H., Tokunaga, T., Liu, X., Takayanagi, S., Matsushima, A., and Shimohigashi, Y., Health Perspect., 2008, vol. 116(1), pp. 32–38. https://doi.org/10.1289/ehp.10587
Lehmler, H.J., Liu, B., Gadogbe, M., and Bao, W., ACS Omega, 2018, vol. 3(6), pp. 6523–6532. https://doi.org/10.1021/acsomega.8b00824
Bisphenol, A., (BPA): Use in Food Contact Application|FDA, 2022. https://www.fda.gov/food/food-additives-petitions/bisphenol-bpa-use-food-contact-application.
Liu, J. and Ishida, H., Macromolecules, 2014, vol. 47(16), pp. 5682–5690. https://doi.org/10.1021/ma501294y
Rochester, J.R. and Bolden, A.L., Environ. Health Perspect., 2015, vol. 123(7), pp. 643–650. https://doi.org/10.1289/ehp.1408989
Salum, M.L., Iguchi, D., Arza, C.R., Han, L., Ishida, H., and Froimowicz, P., ACS Sustain. Chem. Eng., 2018, vol. 6(10), pp. 13096–13106. https://doi.org/10.1021/acssuschemeng.8b02641
Prabunathan, P., Vasanthakumar, A., Manoj, M., Hariharan, A., and Alagar, M., J. Polym. Res., 2020, vol. 27(3). https://doi.org/10.1007/s10965-020-2022-z
Hariharan, A., Srinivasan, K., Murthy, C., and Alagar, M., Ind. Eng. Chem. Res., 2017, vol. 56 (33), pp. 9347–9354. https://doi.org/10.1021/acs.iecr.7b01816
Takeichi, T., Kawauchi, T., and Agag, T., Polym. J., 2008, vol. 40(12), pp. 1121–1131. https://doi.org/10.1295/polymj.PJ2008072
Ishida, H. and Krus, C.M., Macromolecules, 1998, vol. 31(8), pp. 2409–2418. https://doi.org/10.1021/ma970156s
Kiskan, B., Ghosh, N.N., and Yagci, Y., Polym. Int., 2011, vol. 60(2), pp. 167–177. https://doi.org/10.1002/pi.2961
Zhang, W., Lu, X., Xin, Z., and Zhou, C., Nanoscale, 2015, vol. 7(46), pp. 19476–19483. https://doi.org/10.1039/C5NR06425B
Liu, C.T., Su, P.K., Hu, C.C., Lai, J.Y., and Liu, Y.L., J. Memb. Sci., 2018, vol. 546, pp. 100–109. https://doi.org/10.1016/j.memsci.2017.10.018
Li, Y., Yu, Q., Yin, X., Xu, J., Cai, Y., Han, L., Huang, H., Zhou, Y., Tan, Y., Wang, L., and Wang, H., Cellulose, 2018, vol. 25(11), pp. 6691–6704. https://doi.org/10.1007/s10570-018-2024-8
Manickam, M., Pichaimani, P., Arumugam, H., and Muthukaruppan, A., Ind. Eng. Chem. Res., 2019, vol. 58(47), pp. 21419–21430. https://doi.org/10.1021/acs.iecr.9b03440
Hosseini, M., Mertens, S.F.L., Ghorbani, M., and Arshadi, M.R., Mater. Chem. Phys., 2003, vol. 78(3), pp. 800–808. https://doi.org/10.1016/S0254-0584(02)00390-5
Subramanyam, N.C., Sheshadri, B.S., and Mayanna, S.M., Corros. Sci., 1993, vol. 34(4), pp. 563–571. https://doi.org/10.1016/0010-938X(93)90272-I
Shi, X., Nguyen, T.A., Suo, Z., Liu, Y., and Avci, R., Surf. Coatings Technol., 2009, vol. 204(3), pp. 237–245. https://doi.org/10.1016/j.surfcoat.2009.06.048
Lu, X., Liu, Y., Zhou, C., Zhang, W., and Xin, Z., RSC Adv., 2016, vol. 6(7), pp. 5805–5811. https://doi.org/10.1039/C5RA22980D
Zhou, C., Lu, X., Xin, Z., Liu, J., and Zhang, Y., Prog. Org. Coatings, 2013, vol.76(9), pp. 1178–1183. https://doi.org/10.1016/j.porgcoat.2013.03.013
Manoj, M., Kumaravel, A., Mangalam, R., Prabunathan, P., Hariharan, A., and Alagar, M., J. Coatings Technol. Res., 2020, vol. 17(4), pp. 921–935. https://doi.org/10.1007/s11998-019-00312-4
Li, P.Z., Liu, Z.Q., Tetrahedron, 2013, vol. 69(46), pp.9898–9905. https://doi.org/10.1016/j.tet.2013.08.053
Thennarasu, P., Prabunathan, P., and Senthilkumar, M., Industrial Textiles, 2017, vol. 47(7), pp. 1609–1625. https://www.fda.gov/food/food-additives-petitions/bisphenol-bpa-use-food-contact-application.
Van Kreelen, D.W. and TeNijenhuis, K., Prop. Polym., 2009.
Vimala, K., Sundarraj, S., Paulpandi, M., Vengatesan, S., and Kannan, S., Process Biochem., 2014, vol. 49(1), pp. 160–172.https://doi.org/10.1016/j.procbio.2013.10.007
Rios, J.L., Recio, M.C., and Villar, A., J. Ethnopharmacol., 1988, vol. 23(2–3), pp. 127–149. https://doi.org/10.1016/0378-8741(88)90001-3
Ahmed, T., Baidya, S., Sharma, B.C., Malek, M., Das, K.K., Acharjee, M., Munshi, S.K., Noor Am. J. Clin. Pathol., 1966, vol. 45(4), pp. 493–496. https://www.fda.gov/food/food-additives-petitions/bisphenol-bpa-use-food-contact-application.
Ning, X. and Ishida, H., J. Polym. Sci., Part A Polym. Chem., 1994, vol. 32(6), pp.1121–1129. https://doi.org/10.1002/pola.1994.080320614
Hung, H.M., Linh, D.K., Chinh, N.T., Duc, L.M., Trung, V.Q., Prog. Org. Coatings, 2019, vol. 131, pp. 407–416. https://doi.org/10.1016/j.porgcoat.2019.03.006
Koga, G.Y., Wolf, W., Schulz, R., Savoie, S., Bolfarini, C., Kiminami, C.S., Botta, W.J., Surf. Coatings Technol., 2019, vol. 357, pp. 993–1003. https://doi.org/10.1016/j.surfcoat.2018.10.101
Zhou, C., Lu, X., Xin, Z., Liu, J., Corros. Sci., 2013, vol. 70, pp. 145–151. https://doi.org/10.1016/j.corsci.2013.01.023
Nayak, S.R. and Mohana, K.N.S., Surfaces and Interfaces, 2018, vol. 11, pp. 63–73. https://doi.org/10.1016/j.surfin.2018.03.002
Zheng, H., Guo, M., Shao, Y., Wang, Y., Liu, B., Meng, G., Corros. Sci., 2018, vol. 139, pp. 1–12. https://doi.org/10.1016/j.corsci.2018.04.036
Sharifi, Z., Pakshir, M., Amini, A., and Rafiei, R., J. Ind. Eng. Chem., 2019, vol. 74, pp. 41–54. https://doi.org/10.1016/j.jiec.2019.01.043
Zhang, Y., Shao, Y., Liu, X., Shi, C., Wang, Y., Meng, G., Zeng, X., and Yang, Y., Prog. Org. Coatings, 2017, vol. 111, pp. 240–247. https://www.fda.gov/food/food-additives-petitions/bisphenol-bpa-use-food-contact-application.
ACKNOWLEDGMENTS
The authors acknowledge the SIF, VIT-Vellore for providing NMR facility.
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
The authors have no conflict of interest.
Supplementary information
Rights and permissions
About this article
Cite this article
Nivinkrishnan, P., Sophia, S.J., Kumaravel, A. et al. Synthesis and Application of Non-Toxic Superhydrophobic Phenyl Substituted Pyrazolidine Based Benzoxazine Coating for Oil-Water Separation and Corrosion Resistance. Russ J Appl Chem 95, 1243–1261 (2022). https://doi.org/10.1134/S1070427222080225
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070427222080225