TY  - JOUR
T1  - Synthesis, Spectroscopic and Thermal Characterization of a New Sustainable Polymer
AU  - Turan, Nevin
AU  - Çankaya, Nevin
PY  - 2021
DA  - December
DO  - 10.54287/gujsa.1026957
JF  - Gazi University Journal of Science Part A: Engineering and Innovation
JO  - GU J Sci, Part A
PB  - Gazi University
WT  - DergiPark
SN  - 2147-9542
SP  - 529
EP  - 536
VL  - 8
IS  - 4
LA  - en
AB  - 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.
KW  - D-limonene
KW  - Sustainable Polymer
KW  - Copolymer
KW  - Synthesis and Characterization
KW  - Thermal Stability
CR  - 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.
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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.
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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.
CR  - 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
CR  - 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
CR  - 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.
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - Sun, J. (2007). D-limonene: Safety and clinical applications. Alternative Medicine Review-A Journal of Clinical Therapeutics, 12(3), 259-264. PubMed:18072821
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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
CR  - 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
UR  - https://doi.org/10.54287/gujsa.1026957
L1  - https://dergipark.org.tr/en/download/article-file/2093983
ER  -