Synthesis and Identification of Heterocyclic Compounds (Oxazepine, Tetrazole) Derived from Benzidine as Photostabilizing for Poly vinyl chloride

Olfat A. Nief

Abstract


This research describes preparation of new four compounds (A2-A5) having 1,3-oxazepine and Tetrazole rings. The first step involves reaction of benzidine (A1) with aromatic aldehyde (cinnamaldehyde) in ethanol as a solvent in the presence of acid as catalyst to yield the Schiff base (A2), Schiff base (A2) was condensed with maleic anhydride and phthalic anhydride in dry benzene to give a seven-membered heterocyclic ring derivative (A3, A4), In addition, we synthesis novel tetrazole derivative (A5) from the reaction of Schiff base (A2) with sodium azide in tetrahydrofuran. The structure of synthesized compounds were identified by spectral methods [FTIR, ¹H-NMR, and ¹³C-NMR] and measurement physical properties. The photo stabilization of poly (vinyl chloride) films by compounds (A1-A5) was studied. The Photostabilization activities of these compounds were determined by monitoring the carbonyl and hydroxyl indexes values with irradiation time. The changes in viscosity average molecular weight of PVC with irradiation time were studied by using tetrahydrofuran as a solvent. The influence of concentrations additives (range 0.1-0.5wt) on the rate of photodegradation and Photostabilization course was studied. Therefore, we found that was an increase Photostabilization rates with increasing concentrations of additives. In addition, Studying the effect of film thickness and the results showed that an increase in film thickness would reduce the rate of photolysis. The results indicated that Photostabilisation proportion of plastic in the presence of additives follow the trend: (PVC blank) > PVC+A1> PVC+A2 > PVC+A5> PVC+A4> PVC+A3. According to the results obtained, it proposed mechanisms depending on the structure of the additive.

Keywords


1,3-Oxazepine, Photochemistry, PVC, Photostabilizer, UV absorber, Tetrazole.

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References


H. Schiff, Ann. Chem. , vol. 131, p. 118, 1864.

P. Saul, "The chemistry of the carbon nitrogen double bond," Ltd., London, (1970.

Ahmed, A., Sarah, M., Anwar, H., Ayad, H. and Emad, Y, "Antibacterial Study of Some Oxazepine Derivatives," Journal of Al -Nahrain University, vol. 18, pp. 22-26, 2015.

Dhanya Sunil 1, Ranjitha C1, Rama M 1, "Oxazepine Derivative as an Antitumor Agent and Snail1 Inhibitor against Human Colorectal Adenocarcinoma," international Journal of Innovative Research in Science, vol. 3, pp. 15357-15363, 2014.

Matsuzaki, H., Takuchi, I., Hamad, Y. and Hatano, K, "Studies on the 1, 4-oxazepine ring formation reaction using the molecular orbital method," Chemical and Pharmaceutical Bulletin, vol. 48, pp. 755 -756, 2000.

Hamak, K. F., Eissa, H. H, "Synthesis, Characterization, and Biological Evaluation and Anti Corrosion Activity of Some Heterocyclic Compounds Oxazepine Derivatives from Schiff Bases," Organic Chemistry Current Research, vol. 2, no. 3, pp. 1-7, 2013.

H. Ayad, "Microwave Synthesis of Some New 1, 3 -Oxazepine Compounds as Photostabilizing Additives for Pmma Films," Journal of Al -Nahrain University , vol. 15, pp. 47-59 , 2012.

T. A. A. –. Khitam, "Synthesis, Identification and Evaluation the Biological Activity for Some New Heterocyclic Compounds Derived from Schiff Bases," Journal of Applied Chemistry , vol. 9, no. 5, pp. 1-11, 2016.

Andrady, A., Hamid, S., Hu, X.and Torikai, A, "Effects of increased solar ultraviolet radiation on materials in Environmental Effects of Ozone Depletion," J. Photochem. Photobiol, vol. 46, p. 96–103, 1988.

Grassie N., Scott, G, "Polymer Degradation and Stabilization," Cambridge University Press, London, 1985.

Diana C. G. A. Pinto., Clementina, M. M. Santos. and Artur, M. S. Silva, "Advanced NMR techniques for structural characterization of heterocyclic structures," Recent Research Developments in Heterocyclic Chemistry, vol. 81, pp. 397-475, 2007.

Arct J., Dul, M., Rabek, J.F. and Ranby, B, "Studies on modified benzotriazoles as photostabilizers for poly (vinyl chloride)," Eurp. Polym.J, vol. 17, pp. 1041-1048, 1981.

Ranby B.G., Rabek, J.F, "Photodegradation, Photooxidation and Photostabilization of Polymers," London: John Wiley & Sons, 1975.

J. Mark, "Physical Properties of Polymers Handbook," Springer, New York, 1988.

Mori, F., Koyama, M.and Oki, Y, "Studies on photodegradation of poly (vinyl chloride)," Die Angewandte Mak-omolekulare Chemie, vol. 64, no. 1, p. 89–99, 2007.

Silverstein, R.M., Basslar, G.C, "Spectroscopic identification of organic compound," 2005.

Fisher, P.E., Lawrence, W, "Selection of Engineering Materials and Adhesives," CRC Press, 2005.

Shyichuk A., White, J, "Analysis of chain –scission and crosslinking rates in the photo –oxidation of polystyrene," Appl. Poly. Sci, vol. 77, no. 13, pp. 3015-3023, 2000.

F. Gugumus, "Mechanism of Polymer Degradation and Stabilization," 1990.

A. N. Olfat, "Photostabilization of polyvinyl chloride by some new thiadiazole derivatives," Eur. J. Chem, vol. 3, no. 6, p. 242‐247, 2015.




DOI: http://dx.doi.org/10.23851/mjs.v28i2.521

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