Studying the photostabilization activity of Poly(Vinyl Chloride) films containing 4-amino-5-(((5-methyl-1H-benzo[d]imidazol-2-yl)thio)methyl)-2,4-dihydro-3H-1,2,4-triazole-3-thiol with a dibutyltin complex

Document Type : Original Research Paper

Authors

1 Department of Chemistry College of Science for Women University of Baghdad, 10071, Baghdad, Iraq

2 Department of Environmental Science, College of Energy and Environmental Science, AlkarkhUniversity of Science, 10081, Baghdad, Iraq

3 School of Chemical Science and Food Technology, Faculty of Science and Technology, UniversityKebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia

4 Polymer Research Unit, College of Science, Al-Mustansiriyah University, 10052, Baghdad, Iraq

5 Department of Chemistry, College of Science, Al-Nahrain University, 47077, Baghdad, Iraq

Abstract

A new traiazole derivative (4-amino-5-(((5-methyl-1H-benzo[d]imidazol-2-yl)thio)methyl)-2,4-dihydro-3H-1,2,4-triazole-3-thiol, (L), was employed as a chelating ligand to form a dibutyltin chloride complex and improve the poly(vinyl chloride) (PVC) properties. The doped PVC films were characterized via FT-IR, UV-Vis spectrum, elemental analyses (C, H, N, and M (metallic)), and magnetic susceptibility and conductivity measurements. These characterizations were conducted at room temperature, and it was disclosed that the chelating ligand rules as a bidentate chelate. The photostabilization examination of plain and L-doped PVC films was conducted in the presence of ambient air using the accelerating weather tester, where the doping ratio was fixed to 0.5 wt.%. The photostabilization performance of the additive was evaluated by tracking the indexes of carbonyl (ICO), polyene (IPO), and hydroxyl (IOH), and weight loss relationship with irradiation time. It was noticed that the values of ICO, Ipo, and IOH enhanced with the irradiation time, where this improvement relied on the presence of the Bu2SnL complex.

Keywords


Abdullah, B. H., Abdullah, M. A., Al-Jibori, S. A. and Talal, A. K. (2007). Platinum (II) Linkage Isomeric Complexes Containing Mixed Ligands 4, 5-diphenyl-1, 2, 4-triazole-3-thione and Diphosphines Ph2P (CH2) nPPh2 (n= 1, 2 or 3). Asian J. Chem., 19(2); 1334.
Abed, R. N., Kadhom, M., Ahmed, D.S., Hadawey, A. and Yousif, E. (2021). Enhancing Optical Properties of Modified PVC and Cr2O3 Nanocomposite. Trans. Electr. Electron. Mater., 22(3); 317-327.
Ahmad, T., Guria, C. and Mandal, A. (2018). Synthesis, characterization and performance studies of mixed-matrix poly (vinyl chloride)-bentonite ultrafiltration membrane for the treatment of saline oily wastewater. Process Saf Environ Prot., 116, 703-717.
Ahmed, D. S., Kadhom, M., Hadi, A. G., Bufaroosha, M., Salih, N., Al-Dahhan, W. H. and Yousif, E. (2021). Tetra Schiff Bases as Polyvinyl Chloride Thermal Stabilizers. Chemistry, 3(1); 288-296.
Al-Dossary, A. K., Gilbert, M. and Hitt, D. (2010). Evaluating PVC degradation using UV and Raman spectroscopies. Adv Mat Res., 83; 923-930
Ali, G. Q., El-Hiti, G. A., Tomi, I. H. R., Haddad, R., Al-Qaisi, A. J. and Yousif, E. (2016). Photostability and performance of polystyrene films containing 1, 2, 4-triazole-3-thiol ring system Schiff bases. Molecules, 21(12); 1699.
Ali, M. M., El-Hiti, G. A. and Yousif, E. (2016). Photostabilizing efficiency of poly (vinyl chloride) in the presence of organotin (IV) complexes as photostabilizers. Molecules, 21(9); 1151.
Alias, M. F. (2007). Synthesis and characterization of some new metal complexes with Bis [4-phenyl- 2-dibutyl aminomethyl-1,2,4-triazole-3-thion-5yl]methane and theoretical study. Al-Nahrain J. Sci., 10(2), 13-24.
Alias,M.F. ,Hashim, A.J. and Kareem, T.A. (2008). Synthesis and Characterization of Some Inorganic Compounds and Study their Effect in activity of Laccase Produced by Fungal isolate Pleurotus ostreatus. Ibn Al-haitham J. for pure & appl. sci. 21 (2)
Al-Jibouri, M. N., Al-Ameri, S. A., Al-Jibouri, W. M. and Al-Souz, M. A. (2013). Spectroscopic study of the effect of a new metal chelate on the stability of PVC. J Assn Arab Univ Basic Appl Sci., 14(1); 67-74.
Awad, A. A., Al-Hasan, R. A. and Yousif, E. A. (2016). Study The Rate Constant of Photodecomposition of Polystyrene Films in Presence of Some 4-amino-5-(2-(6- methoxynaphthalen-2-yl) piperidino)-1, 2,   4-triazole-3-thion   Complexes. Al-Nahrain   J. Sci., 19(1); 69-75.
Boughattas, I., Ferry, M., Dauvois, V., Lamouroux, C., Dannoux-Papin, A., Leoni, E. and Esnouf, S. (2016) Thermal degradation of γ-irradiated PVC: I-dynamical experiments. Polym. Degrad. Stab., 126; 219-226.
de Souza, M. J. B., Silva, T. H. A., Ribeiro, T. R. S., da Silva, A. O. S. and Pedrosa, A. M. G. (2019). Thermal and catalytic pyrolysis of polyvinyl chloride using micro/mesoporous ZSM-35/MCM- 41 catalysts. J. Therm. Anal. Calorim., 140; 167-175.
Decker, C. and Balandier, M. (1981). Photo-oxidation of poly (vinyl chloride). Polym Photochem 1(3); 221-232.
Fizer, O., Fizer, M. and Studenyak, Y. (2017). Photostability of plasticized polyvinyl chloride membranes: A theoretical study. Malaysian Anal Sci .J., 21(6); 1257-1265.
Folarin, O. M. and Sadiku, E. R. (2011). Thermal stabilizers for poly (vinyl chloride): A review. Int. J. Phys. Sci, 6(18), 4323-4330.
Gardette, J.-L.; Gaumet, S.; and Lemaire, J. (1989) Photooxidation of poly(vinyl chloride). 1. A reexamination of the mechanism. Macromolecules, 22, 2576–2581.
Gaumet, S. and Gardette, J. L. (1991). Photo-oxidation of poly (vinyl chloride): Part 2—A comparative study of the carbonylated products in photo-chemical and thermal oxidations. Polym. Degrad. Stab., 33(1); 17-34.
Gesenhues, U. (2000). Influence of titanium dioxide pigments on the photodegradation of poly (vinyl chloride). Polym. Degrad. Stab., 68(2); 185-196.
Gugumus, F. (1990), Mechanism of Polymer Degradation and Stabilization, Elsevier, Amsterdam. Gusev, A  N , Shul’gin, V F , Konnic, O. V., Meshkova, S. B., Aleksandrov, G. G., Kiskin, M. A. and
Linert, W. (2011). New Zn complexes based on 1, 2, 4-triazoles: Synthesis, structure and luminescence. Inorganica Chim. Acta., 376(1); 509-514.
Haddad, R. (2019). Photochemical Study of Different Thicknesses of Polystyrene Films Containing Ni
(II) Complex against photodegradation. Al-Nahrain J. Sci., 22(4); 30-41.
Hadi, A. G., Yousif, E., El-Hiti, G. A., Ahmed, D. S., Jawad, K., Alotaibi, M. H. and Hashim, H. (2019). Long-term effect of ultraviolet irradiation on poly (vinyl chloride) films containing naproxen diorganotin (IV) complexes. Molecules, 24(13); 2396.
Hasan, M., Banerjee, A. N. and Lee, M. (2015). Enhanced thermo-optical performance and high BET surface area of graphene@ PVC nanocomposite fibers prepared by simple facile deposition technique: N2 adsorption study. J Ind Eng Chem., 21; 828-834.
Hassan, O. A. and Otaiwi, A. M. (2008). Photodegradation Study of PVC by New Metal Complexes of Thiourea Derivatives. Iraqi Nat. J. Chem., (31); 501-513.
Hussain, Z., Alsayed, R., Alwash, A., Ahmed, A., Noaman, R., Jawad, A. H. and Yousif, E. (2019). Controlling the Photo-Degradation Rate Constant of PS Containing Nickel (II) Complex. Al- Nahrain J. Sci., 22(3); 8-17.
Joshi, R., Kumari, A., Singh, K., Mishra, H. and Pokharia, S. (2019). New diorganotin (IV) complexes of Schiff base derived from 4‐amino‐3‐hydrazino‐5‐mercapto‐4H‐1, 2, 4‐triazole: Synthesis, structural characterization, density functional theory studies, atoms‐in‐molecules analysis and antifungal activity. Appl. Organomet. Chem., 33(5); e4894.
La Mantia, F. P. and Morreale, M. (2008). Accelerated weathering of polypropylene/wood flour composites. Polym. Degrad. Stab., 93(7); 1252-1258.
Ma, Y., Song, F., Hu, Y., Kong, Q., Liu, C., Rahman, M. A. and Jia, P. (2020). Highly branched and nontoxic plasticizers based on natural cashew shell oil by a facile and sustainable way. J. Clean. Prod., 252; 119597.
Maouz, H., Khaouane, L., Hanini, S., Ammi, Y., Hamadache, M. and Laidi, M. (2020). QSPR Studies of Carbonyl, Hydroxyl, Polyene Indices, and Viscosity Average Molecular Weight of Polymers under Photostabilization Using ANN and MLR Approaches. Kemija u industriji: Časopis kemičara i kemijskih inženjera Hrvatske, 69(1-2); 1-16.
Mark, J. E. (Ed.). (2007). Physical properties of polymers handbook 1076; 825. New York: Springer. Mohamed, S. H., Hameed, A. S., El-Hiti, G. A., Ahmed, D. S., Kadhom, M., Baashen, M. A.,
Bufaroosha, M., Ahmed, A. A. and Yousif, E. (2021). A process for the synthesis and use of highly aromatic organosilanes as additives for poly (vinyl chloride) films. Processes, 9(1); 91.
Mohammed, A., Kadhom, M. and Yousif, E. (2021). Tin (IV) Compounds as Photo-Stabilizers for Irradiated Surfaces of Poly (Vinyl Chloride) Films. Surfaces, 4(4); 279-292.
Naif, O. A. (2011). Synthesis of new modified PVC and their photostability study. Tikrit J. Pure Sci., 16(4); 101-117.
Okoro, H. K., Fatoki, O. S., Adekola, F. A., Ximba, B. J. and Snyman, R. G. (2011). Sources environmental levels and toxicity of organotin in marine environment: a review. Instit. Repos., 23(2); 473-482
Rabie, S. T. and Khalil, A. M. (2012). Antimicrobial agents as photostabilizers for rigid poly (vinyl chloride). Polym Adv Technol., 23(10); 1394-1402.
Rabinovitch, E. B., Dorsch, J. L., Summers, J. W. and Quisenberry, J. G. (1986). Role of organotin mercaptide stabilizer in heat and light stability of PVC. J. Vinyl Addit. Technol., 8(2); 73-78.
Salman, H. N., Nief, O. A. and Ahmed, A. A. (2018). New Stabilizers for Poly (vinyl chloride) Derived from 1, 1-Bis (4-aminophenyl)-4-Phenyl Cyclohexane Compounds [II]. Al-Nahrain J. Sci., 21(3); 61-69.
Singh, K., Kumar, Y., Puri, P., Sharma, C. and Aneja, K. R. (2011). Metal-based biologically active compounds: synthesis, spectral, and antimicrobial studies of cobalt, nickel, copper, and zinc complexes of triazole-derived Schiff bases. Bioinorg Chem Appl., 2011, 901716.
Su, Q., Mao, J., Zhao, G. and Zhang, M. (1997). A study on the structure of degraded PVC by photoacoustic spectroscopy. J. Mol. Struct., 403(3); 231-236.
Su, X , Ng, H T , Dai, C C , O’Shea, S J. and Li, S. F. Y. (2000). Disposable, low cost, silver-coated, piezoelectric quartz crystal biosensor and electrode protection. Analyst, 125(12); 2268-2273.
Symal, A.; Bari Niazi, M. A. (1984). Synthesis of new Schiff bases derived from 4-amino-5-mercapto- 3-methyl-1,2,4-triazole & salicylaldehyde or substituted salicylaldehyde & their copper(II) complexes. Indian J. Chem., 23A, 163–165.
Vymazal, Z. and Vymazalova, Z. (1991). Photodegradation of PVC stabilized by organotin compounds. Eur. Polym. J., 27(11); 1265-1270.
Wang, X., Ma, B., Wang, Y., Lu, S., Ma, M., Shi, Y. and Chen, S (2019) A new theory of “two-step stabilization mechanism” for triazole-based zinc-containing complex as thermal stabilizer for poly (vinyl chloride). Polym. Degrad. Stab., 167; 86-93.
Watheq, B., Yousif, E., Al-Mashhadani, M. H., Mohammed, A., Ahmed, D. S., Kadhom, M. and Jawad, A. H. (2020). A Surface Morphological Study, Poly (Vinyl Chloride) Photo-Stabilizers Utilizing Ibuprofen Tin Complexes against Ultraviolet Radiation. Surfaces 3(4); 579-593.
Xiang, X., Chen, S., Zhang, J. and Huang, X. (2010). Effect of relatively nontoxic thermal stabilizers on photodegradation of poly (vinyl chloride). Polym. Eng. Sci., 50(6); 1095-1104.
Yang, X., Jiang, X., Hu, J., Wang, F. and Hu, C. (2017). Relationship between physical and mechanical properties of accelerated weathering and outdoor weathering of PVC-coated membrane material under tensile stress. J. Ind. Text., 47(2); 197-210.
Yousif, E., Salih, N. and Salimon, J. (2011). Improvement of the photostabilization of PVC films in the presence of 2N‐salicylidene‐5‐(substituted)‐1, 3, 4‐thiadiazole. J. Appl. Polym. Sci., 120(4); 2207-2214.