Synthesis of Zn(II) and Co(II) Complexes with a Schiff Base Derived from Malonic Acid Dihydrazide for Photo-Stabilizers of Polystyrene

https://doi.org/10.22146/ijc.83730

Rehab Ghalib Hammoda(1), Naser Shaalan(2*)

(1) Department of Chemistry, College of Science for Women, University of Baghdad, Baghdad 10071, Iraq
(2) Department of Chemistry, College of Science for Women, University of Baghdad, Baghdad 10071, Iraq
(*) Corresponding Author

Abstract


In this study, novel Schiff base complexes with Zn(II) and Co(II) ions were successfully synthesized. The malonic acid dihydrazide was converted into the Schiff base ligand by combining it with 1-hydroxy-2-naphthaldehyde, and the last step required reacting it with the appropriate metal(II) chloride to produce pure target complexes. The generated complexes were thoroughly characterized using FTIR, 1H-NMR, 13C-NMR, GC-mass, and UV-Vis spectroscopies. In order to photo-stabilize polystyrene (PS) and reduce the photodegradation of its polymeric chains, these chemicals have been used in this work. The efficiency of the generated complexes as photo-stabilizers was evaluated using a variety of techniques, including FTIR, weight loss, viscosity average molecular weight, light and atomic force microscopy, scanning electron microscopy (SEM), and energy dispersive X-ray (EDX) mapping. These tests corroborated each other and demonstrated how effectively new compounds stabilize PS photographs. As a result, compared to blank PS, they reduce the photodegradation of PS films containing these complexes after 300 h of exposure to UV radiation with a wavelength of 313 nm. Also, it has demonstrated how effective the cobalt complex is as a photo-stabilizer. The highly conjugated systems in these chemicals are to blame for this.


Keywords


photodegradation; malonyldihydrazide; phytostabilization; polystyrene; Schiff base complexes



References

[1] Basha, M.H., Sulaiman, S.A., and Uemura, Y., 2020, Co-gasification of palm kernel shell and polystyrene plastic: Effect of different operating conditions, J. Energy Inst., 93 (3), 1045–1052.

[2] Al-Mashhadani, M.H., Thamer, H., Adil, H., Ahmed, A., Ahmed, D.S., Bufaroosha, M., Jawad, A.H., and Yousif, E., 2021, Environmental and morphological behavior of polystyrene films containing Schiff base moiety, Mater. Today: Proc., 42, 2693–2699.

[3] Wang, J., Wang, X., Zhao, S., Sun, B., Wang, Z., and Wang, J., 2020, Robust superhydrophobic mesh coated by PANI/TiO2 nanoclusters for oil/water separation with high flux, self-cleaning, photodegradation and anti-corrosion, Sep. Purif. Technol., 235, 116166.

[4] Zabaniotou, A., and Kassidi, E., 2003, Life cycle assessment applied to egg packaging made from polystyrene and recycled paper, J. Cleaner Prod., 11 (5), 549–559.

[5] Wu, Y., Dong, L., Shu, X., Yang, Y., She, W., and Ran, Q., 2022, A review on recent advances in the fabrication and evaluation of superhydrophobic concrete, Composites, Part B, 237, 109867.

[6] Rabie, S.T., Ahmed, A.E., Sabaa, M.W., and Abd El-Ghaffar, M.A., 2013, Maleic diamides as photostabilizers for polystyrene, J. Ind. Eng. Chem., 19 (6), 1869–1878.

[7] Liu, X., Sun, P., Qu, G., Jing, J., Zhang, T., Shi, H., and Zhao, Y., 2021, Insight into the characteristics and sorption behaviors of aged polystyrene microplastics through three type of accelerated oxidation processes, J. Hazard. Mater., 407, 124836.

[8] Li, Y., Li, J., Ding, J., Song, Z., Yang, B., Zhang, C., and Guan, B., 2022, Degradation of nano-sized polystyrene plastics by ozonation or chlorination in drinking water disinfection processes, Chem. Eng. J., 427, 131690.

[9] Khalaf, M., Fadhil, Z., Al-Mashhadani, M.H., Abdallh, M., Bufaroosha, M., Majeed, A., Salih, N., and Yousif, E., 2020, PVC films performance stabilized by dibutyltin(IV) complex for sustainable environment, J. Phys.: Conf. Ser., 1664, 012072.

[10] Ahmed, A., Al-Mashhadani, M.H., Ahmed, D.S., Ahmed, A.A., Yousif, E., and Yusop, R.M., 2021, Preparation of polymeric films containing Schiff base as UV-absorber with good resistance against UV-photoaging, Biointerface Res. Appl. Chem., 11, 12743–12749.

[11] Al-Mashhadani, M.H., Salman, E.A., Husain, A.A., Abdallh, M., Bufaroosha, M., and Yousif, E., 2022, Utilizing organic aromatic melamine moiety to modify poly(vinyl chloride) chemical structure and micro CuO that plays an important role to enhance its photophysical features, Indones. J. Chem., 22 (5), 1187–1194.

[12] Jima'a, R.B., and Shaalan, N., 2023, Synthesis, characterization, and biological activity of new metal ion complexes with Schiff base derived from 2-acetylthiophene and isatin, Egypt. J. Chem., 65 (132), 1409–1419.

[13] Ahmed, D.S., Mohammed, A., Husain, A.A., El-Hiti, G.A., Kadhom, M., Kariuki, B.M., and Yousif, E., 2022, Fabrication of highly photostable polystyrene films embedded with organometallic complexes, Polymers, 14 (5), 1024.

[14] Fadhil, Z., Zageer, D.S., Faris, A.H., Al-Mashhadani, M.H., Ahmed, A., Hashim, H., and Yousif, E., 2022, Extracted lignin from oil palm empty fruit bunch as natural eco-friendly poly(vinyl chloride) photo-stabilizer, Mater. Sci. Energy Technol., 5, 15–21.

[15] Jose, T.S., Rajesh, C., Puthukkara, P.A.R., Unnikrishnan, K.S., and Arun, K.J., 2021, Accelerated photodegradation of polystyrene by TiO2-polyaniline photocatalyst under UV radiation, Eur. Polym. J., 153, 110493.

[16] Zhang, X., Su, H., Gao, P., Li, B., Feng, L., Liu, Y., Du, Z., and Zhang, L., 2022, Effects and mechanisms of aged polystyrene microplastics on the photodegradation of sulfamethoxazole in water under simulated sunlight, J. Hazard. Mater., 433, 128813.

[17] Mahdi, S.A., Ahmed, A.A., Yousif, E., Al-Mashhadani, M.H., Ahmed, A., Hashim, H., and Jawad, A.H., 2022, New organic PVC photostabilizers derived from synthesised novel coumarine moieties, Mater. Sci. Energy Technol., 5, 278–293.

[18] Ali, A.A., Karasu, B., Allazov, M.R., and Ilyasli, T.M., 2013, Synthesis and study of CexPrxMg1-2xAl2O4 ceramic pigment by combustion method using malonic acid dihydrazide as fuel, Int. J. Sci. Eng. Res., 4 (8), 1686–1690.

[19] Hussein, K.A., and Shaalan, N., 2022, Synthesis, characterization, and antibacterial activity of lanthanide metal complexes with Schiff base ligand produced from reaction of 4,4-methylene diantipyrine with ethylenediamine, Indones. J. Chem., 22 (5), 1365–1375.

[20] Shaalan, N., Khalaf, W.M., and Mahdi, S., 2022, Preparation and characterization of new tetra-dentate N2O2 Schiff base with some of metal ions complexes, Indones. J. Chem., 22 (1), 62–71.

[21] Shaalan, N.D., and Abdulwahhab, S., 2021, Synthesis, characterization and biological activity study of some new metal complexes with Schiff’s bases derived from [Ο-vanillin] with [2-amino-5-(2-hydroxy-ohenyl)-1,3,4-thiadiazole], Egypt. J. Chem., 64 (8), 4059–4067.

[22] Tazin, N., Ragole, V.D., and Wankhede, D.S., 2019, Facile one pot synthesis of tetraamide macrocyclic complexes using malonyldihydrazide and p-nitrobenzaldehyde at room temperature, Inorg. Nano-Met. Chem., 49 (9), 291–296.

[23] Jimaa, R.B., and Shaalan, N., 2022, Synthesis, characterization and biological activity new metal ion complexes with Schiff’s bases derived from 2-Acetylthiophene and Isatin, Egypt. J. Chem., 65 (13), 1409–1419.

[24] Hussein, K.A., Mahdi, S., and Shaalan, N., 2023, Synthesis, spectroscopy of new lanthanide complexes with Schiff base derived from (4-antipyrinecarboxaldehyde with ethylene di-amine) and study the bioactivity, Baghdad Sci. J., 20 (2), 469–482.

[25] Majeed, N.M., Abd. Al-Sahab, S., and Al Shemary, R.K., 2021, Eco-friendly and efficient composition, diagnosis, theoretical, kinetic studies, antibacterial and anticancer activities of mixed some metal complexes of tridentate Schiff base ligand, Int. J. Pharm. Res., 13 (1), 3358–3369.

[26] Mohan, B., and Shaalan, N., 2023, Highly thermally stable and biologically active compounds prepared to be polymer stabilizers consisting of a Schiff base and its complexes derived from 2-hydroxynaphthaldehyde, J. Med. Chem. Sci., 6 (2), 355–364.

[27] Alpay, A., Tuna, Ö., and Simsek, E.B., 2020, Deposition of perovskite-type LaFeO3 particles on spherical commercial polystyrene resin: A new platform for enhanced photo-Fenton-catalyzed degradation and simultaneous wastewater purification, Environ. Technol. Innovation, 20, 101175.

[28] Xiao, L., Zhao, Y., Jin, B., Zhang, Q., Chai, Z., and Peng, R., 2020, Synthesis of novel ultraviolet stabilizers based on [60]fullerene and their effects on photo-oxidative degradation of polystyrene, Fullerenes, Nanotubes Carbon Nanostruct., 28 (6), 465–473.

[29] Fakhri, L.A., Ghanbarzadeh, B., Dehghannya, J., Hosseini, M., and Dadashi, S., 2021, Photo-catalytic and biotic degradation of polystyrene packaging film: Effect of zinc oxide photocatalyst nanoparticles and nanoclay, Chemosphere, 283, 130972.

[30] Luna, C.B.B., Siqueira, D.D., Araújo, E.M., and Fook, M.V.L., 2020, Photodegradation of polystyrene/rubber waste blends compatibilized with SBS copolymer, J. Elastomers Plast., 52 (4), 356–379.

[31] Yousif, E., Haddad, R., El-Hiti, G.A., and Yusop, R.M., 2017, Spectroscopic and photochemical stability of polystyrene films in the presence of metal complexes, J. Taibah Univ. Sci., 11 (6), 997–1007.

[32] Mageed, Z.N., Kadhium, S.S., Rodhan, W.F., and Mohammed, H.H., 2022, Study of the photostabilization of polystyrene in the presence and absence of Schiff base derivatives, Egypt. J. Chem., 65 (4), 675–683.

[33] Fajstavr, D., Neznalová, K., Švorčík, V., and Slepička, P., 2019, LIPSS structures induced on graphene-polystyrene composite, Materials, 12 (21), 3460.

[34] Slepička, P., Neznalová, K., Fajstavr, D., and Švorčík, V., 2020, Nanostructuring of honeycomb-like polystyrene with excimer laser, Prog. Org. Coat., 145, 105670.

[35] Nguyen, T.N., Rangel, A., and Migonney, V., 2021, Fibronectin adsorption on polystyrene sulfonate-grafted polyester using atomic force microscope, Biointerphases, 16 (5), 051003.



DOI: https://doi.org/10.22146/ijc.83730

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