Synthesis, Spectroscopic and Thermal Characterization of a New Sustainable Polymer

Yıl 2021, Cilt: 8 Sayı: 4, 529 - 536, 30.12.2021

Nevin Çankaya Nevin Turan

https://doi.org/10.54287/gujsa.1026957

Öz

Copolymerization is a very important method in the synthesis of products having the physical and chemical properties sought in industrial sense. In this paper, the copolymerization of N-(4-nitrophenyl) acrylamide monomer with D-limonene was carried out and LIM-co-NPA copolymer was synthesized by free radical chain polymerization reaction. The structure of sustainable copolymer of limonene was chemically characterized by FT-IR, ¹H-NMR spectroscopic techniques. In addition, thermal stability of copolymer investigated by TGA/DTG/DTA simultaneous thermal analysis methods. The spectroscopic results are compatible with the amide or limonene polymers synthesized in the literature. From the important thermal results of the sustainable copolymer, it has been found that the initial decomposition temperature is 226°C, and the maximum decomposition temperatures is 329°C, glass transition temperature at 261°C and crystallization temperature at 340°C. It can be said that this promising sustainable copolymer is suitable for other mechanical, physical and biological study and research fields.

Anahtar Kelimeler

D-limonene, Sustainable Polymer, Copolymer, Synthesis and Characterization, Thermal Stability

Kaynakça

• Adiguzel, R., Ergin, Z., Sekerci, M., & Tascioglu, S. (2011). Synthesis and structural characterization of bis(2-amino-1,3,4-thiadiazolyl)methane complexes. Journal of the Chemical Society of Pakistan, 33(2), 238-244.
• Arrieta, M. P., López, J., Ferrándiz, S., & Peltzer, M. A. (2013). Characterization of PLA-limonene blends for food packaging applications. Polymer Testing, 32(4), 760-768. doi:10.1016/j.polymertesting.2013.03.016
• Bacanlı, M., Başaran, A. A., & Başaran, N. (2018). Effects and Usage of a Citrus Compound, Limonene. In: R. R. Watson, V. R. Preedy, & S. Zibadi (Eds.) Polyphenols: Prevention and Treatment of Human Disease (Second Ed.) (pp. 419-424). Cambridge: Academic Press. doi:10.1016/B978-0-12-813008-7.00032-1
• Bingöl, M., & Turan, N. (2020). Schiff base and metal(II) complexes containing thiophene-3-carboxylate: Synthesis, characterization and antioxidant activities. Journal of Molecular Structure, 1205, 127542. doi:10.1016/j.molstruc.2019.127542
• Brum, F. J. B., Laux, F. N., & Forte, M. M. C. (2013). Synthesis of hydrocarbon polymers by cationic polymerization and their thermal properties. Designed Monomers and Polymers, 16(3), 291-301. doi:10.1080/15685551.2012.747145
• Coşkun, D., Gündüz, B., & Coşkun, M. F. (2019). Synthesis, characterization and significant optoelectronic parameters of 1-(7-methoxy-1-benzofuran-2-yl) substituted chalcone derivatives. Journal of Molecular Structure, 1178, 261-267. doi:10.1016/j.molstruc.2018.10.043
• Coşkun, M., Erol, İ., Coşkun, M. F., & Demirelli, K. (2002). Thermal degradation behavior of two methacrylate polymers with side chain amide groups. Polymer Degradation and Stability, 78(1), 49-55. doi:10.1016/S0141-3910(02)00118-0
• Çankaya, N., & Temüz, M. M. (2012). Characterization and monomer reactivity ratios of grafted cellulose with N-(4-nitrophenyl)acrylamide and methyl methacrylate by atom transfer radical polymerization. Cellulose Chemistry and Technology, 46(9-10), 551-558.
• Çankaya, N., Tanış, E., Elmalı, H. G., & Bulut, N. (2019). A new synthesize of limonene copolymer: Experimental and theoretical analysis. Polymer Bulletin, 76(7), 3297-3327. doi:10.1007/s00289-018-2543-3
• Çankaya, N., Tanış, E., & Sapan, P. G. (2021). New synthesis of homopolymer and limonene copolymer: Experimental analysis and density functional theory study. Russian Journal of Physical Chemistry A, 95(1), 139-153. doi:10.1134/S0036024421010052
• Farhat, A., Fabiano-Tixier, A-S., Maataoui, M. E., Maingonnat, J-F., Romdhane, M., & Chemat, F. (2011). Microwave steam diffusion for extraction of essential oil from orange peel: Kinetic data, extract’s global yield and mechanism. Food Chemistry, 125(1), 255-261. doi:10.1016/j.foodchem.2010.07.110
• Guyton, K. Z., & Kensler, T. W. (2002). Prevention of liver cancer. Current Oncology Reports, 4(1), 464-470. doi:10.1007/s11912-002-0057-4
• Hajizadeh, M. R., Maleki, H., Barani, M., Fahmidehkar, M. A., Mahmoodi, M., & Torkzadeh-Mahani, M. (2019). In vitro cytotoxicity assay of D-limonene niosomes: an efficient nano-carrier for enhancing solubility of plant-extracted agents. Research in Pharmaceutical Sciences, 14(5), 448-458. doi:10.4103/1735-5362.268206
• Hartsel, J. A., Eades, J., Hickory, B., & Makriyannis, A. (2016). Cannabis Sativa and Hemp. In: R. C. Gupta (Eds.) Nutraceuticals: Efficacy, Safety and Toxicity (pp. 735-754). Elsevier Inc: London. doi:10.1016/B978-0-12-802147-7.00053-X
• Kurt, A., Gündüz, B., İlter, Z., & Koca M. (2019a). Optoelectronic properties of 3-acetyl-6-bromocoumarin compound in various solvents and concentrations. Kuwait Journal of Science, 46(3), 60-70.
• Kurt, A., Gündüz, B., & Koca, M. (2019b). A detailed study on the optical properties of 3-benzoyl-7-hydroxy coumarin compound in different solvents and concentrations. Macedonian Journal of Chemistry and Chemical Engineering, 38(2), 227-236. doi:10.20450/mjcce.2019.1403
• Kurt, A., Andan, H., & Koca, M. (2020). Synthesis and characterization of a new bithiazole-containing conjugated polymer and its thermal decomposition kinetics. Macedonian Journal of Chemistry and Chemical Engineering, 39(2), 227-237. doi:10.20450/mjcce.2020.2025
• Lu, X-g., Feng, B-a., Zhan, L-b., & Yu, Z-h. (2003). D-limonene induces apoptosis of gastric cancer cells. Chinese Journal of Oncology, 25(4), 325-327.
• Monica, F. D., & Kleij A. W. (2020). From terpenes to sustainable and functional polymers. Francesco Polymer Chemistry, 11(32), 5109-5127. doi:10.1039/D0PY00817F
• Murali, R., Karthikeyan, A., & Saravanan, R. (2013). Protective effects of D-limonene on lipid peroxidation and antioxidant enzymes in streptozotocin-induced diabetic rats. Basic & Clinical Pharmacology &Toxicology, 112(3), 175-181. doi:10.1111/bcpt.12010
• Neumann, S., Hu, P., Bretschneider, F., Schmalz, H., & Greiner A. (2021). Blends of bio-based poly(limonene carbonate) with commodity polymers. Macromolecular Materials and Engineering, 306(7), 2100090. doi:10.1002/mame.202100090
• Ren, S., Trevino, E., & Dube, M. A. (2015). Copolymerization of limonene with n-butyl acrylate. Macromolecular Reaction Engineering, 9(4), 339-349. doi:10.1002/mren.201400068
• Sharma, S., & Srivastava, A. K. (2003). Alternating copolymers of limonene with methyl methacrylate: kinetics and mechanism. Journal of Macromolecular Science Part A Pure and Applied Chemistry, 40(6), 593-603. doi:10.1081/MA-120020867
• Sharma. S., & Srivastava, A. K. (2004). Synthesis and characterization of copolymers of limonene with styrene initiated by azobisisobutyronitrile. European Polymer Journal, 40(9), 2235-2240. doi:10.1016/j.eurpolymj.2004.02.028
• Sharma, S., & Srivastava, A. K. (2006). Radical co-polymerization of limonene with N-vinyl pyrrolidone: Synthesis and characterization. Designed Monomers and Polymers, 9(5), 503-516. doi:10.1163/156855506778538001
• Singh, A., & Kamal, M. (2012). Synthesis and characterization of polylimonene: Polymer of an optically active terpene. Journal of Applied Polymer Science, 125(2), 1456-1459. doi:10.1002/app.36250
• Souto, E. B., Zielinska, A., Souto, S. B., Durazzo, A., Lucarini, M., Santini, A., Silva, A. M., Atanasov, A. G., Marques, C., Andrade, L. N., & Severino, P. (2020). (+)-Limonene 1,2-epoxide-loaded SLNs: Evaluation of drug release, antioxidant activity, and cytotoxicity in an HaCaT cell line. International Journal of Molecular Sciences, 21(4), 1449. doi:10.3390/ijms21041449
• Sun, J. (2007). D-limonene: Safety and clinical applications. Alternative Medicine Review-A Journal of Clinical Therapeutics, 12(3), 259-264. PubMed:18072821
• Tanış, E., Çankaya, N., & Yalçın, S. (2019). Synthesis, characterization, computation of global reactivity descriptors and antiproliferative activity of N-(4-nitrophenyl)acrylamide. Russian Journal of Physical Chemistry B, 13(1), 49-61. doi:10.1134/S1990793119010147
• Temüz, M. M. (2017). Radical copolymerization of acrloylmorpholine with 2-hydroxyethyl methacrylate: Monomer reactivity ratios and thermal properties. Anadolu University Journal of Science and Technology A-Applied Sciences and Engineering, 18(5), 929-938. doi:10.18038/aubtda.306626
• Turan, N., & Şekerci, M. (2009). Metal complexes of Schiff base derived from terephthalaldehyde and 2-amino-5-ethyl-1,3,4-thiadiazole synthesis, spectral and thermal characterization. Synthesis and Reactivity in Inorganic Metal-Organic and Nano-Metal Chemistry, 39(10), 651-657. doi:10.1080/15533170903433162
• Yu, X., Lin, H., Wang, Y., Lv, W., Zhang, S., Qian, Y., Deng, X., Feng, N., Yu, H., & Qian, B. (2018). D-limonene exhibits antitumor activity by inducing autophagy and apoptosis in lung cancer. OncoTargets and Therapy, 11, 1833-1847. doi:10.2147/OTT.S155716
• Zhang, X., Fevre, M., Jones, G. O., & Waymouth, R. M. (2018). Catalysis as an enabling science for sustainable polymers. Chemical Reviews, 118(2), 839-885. doi:10.1021/acs.chemrev.7b00329
• Zhang, Y., & Dubé, M. A. (2014). Copolymerization of N-butyl methacrylate and D-limonene. Macromolecular Reaction Engineering, 8(12), 805-812. doi:10.1002/mren.201400023
• Zhang, Y., & Dubé, M. A. (2015). Copolymerization of 2-ethylhexyl acrylate and D-limonene, copolymerization of 2-ethylhexyl acrylate and D-limonene. Polymer-Plastics Technology and Engineering, 54(5), 499-505. doi:10.1080/03602559.2014.961080