Asetil Benzofuran Metakrilat Kopolimerlerinin Termal Özelliklerinin ve Reaktivite Oranlarının İncelenmesi

Year 2018, Volume: 18 Issue: 1, 103 - 111, 30.04.2018

Zülfiye İlter Zehra Ergen Serpil Yılmaz

Abstract

2-asetil benzofuril metilmetakrilat (ABM) ve akrilonitril (AN), başlatıcı olarak benzoil peroksit kullanılarak 60°C'de 1,4-dioksan çözücüsünde serbest radikal polimerizasyonu ile hazırlanmıştır. Kopolimer karakterizasyonu için 1H-NMR spektrofotometresi kullanılmıştır. Kopolimerdeki monomer kompozisyonları elementel analiz ile belirlenmiş ve reaktivite oranları (r1 ve r2) Finemann-Ross (FR) ve Kelen-Tüds (KT) olmak üzere çeşitli doğrusal yöntemler kullanılarak hesaplanmıştır. ABM (1) ve AN (2)’nin reaktivite oranları sırasıyla 6,67 ve 0,17 olarak tespit edilmiştir. Molekül ağırlığı jel permasyon kromatografisi (GPC) ile belirlenmiş, heterojendik indeksi (Mw/Mn) 1,13 olarak bulunmuştur. Polimerlerin camsı geçiş sıcaklığı Shimadzu DSC-50 ile incelenmiş olup, camsı geçiş sıcaklıklarının (Tg), kopolimerdeki polar monomer (ABM) konsantrasyonu arttıkça arttığı gözlenmiştir. Polimerlerin termal analizi, Shimadzu TG-50 ile incelenmiş ve kopolimerlerin yüksek sıcaklığa dayanıklı olmadığı görülmüştür.

Keywords

2-Asetil benzofuran metakrilat-ko-akrilonitril, Termal analiz, Reaktivite oranları.

References

• Aguilar, M. R., Gallardo, A., del Mar Fernandez, M., San Roman, J., Cifuentes, A., 2002. Micellar electro kinetic chromatography: a powerful analytical tool to study copolymerization reactions involving ionic species. Macromolecules, 35(6), 2036–2041.
• Allen, N.S., Khan, L., Edge, M., Billings, M., Vercs, J., 1998. Studies on UV and thermally radical in duced cross‐linked polymer networks as charge‐transport layers in electro photographic coating applications. Journal of Photo chemistry and Photobiology A: Chemistry, 116, 235‐244.
• Banihashemi, A. and Abdolmaleki, A., 2004. Novel aromatic polyimides derived from benzofuro (2,3-b) benzofuran-2,3,8,9-tetracarboxylic dianhydride (BBTDA). Europen Polymer Journal, 40, 1629-1635.
• Baysal, B., 1994. Polimer Kimyası, ODTÜ, ANKARA, 9-12. Chen, D., Singh, D., Sirkar, K.K., Pfeffer, R., 2015. Continuous synthesis of polymer-coated drug particles by poroushollow fiber membrane-bas ed anti solvent crystallization. Langmuir, 31(1), 432-41.
• Chen, Y., Liu, C., Chen, Z., Su, C., Hageman, M., Hussain, M., Haskell, R., Stefanski, K., Qian, F., 2015. Drug-polymer-water interaction and its implication for the dissolution performance of amorphous solid dispersions. Molecular Pharmaceutics, 12(2), 576-89.
• Coşkun, M. F., Şentürk, A., Coşkun, D., 2016. Synthesis, characterization of chalcone containing methacrylate polymers: investigation of fluorescence, thermal and dielectric properties. Afyon Kocatepe University Journal of Science and Engineering, 16, 230‐238.
• Çakmak, İ., İlter, Z., Örek, C., 2011. 2-Asetil benzofuran-metakrilat kopolimerinin sentezi, karakterizasyonu ve anti mikrobiyal etkilerinin araştırılması. Science Journal of Bingöl Universty, 1(2), 17-23.
• Darvishi, A., Mohammad, J., Mehr, Z., Marandi, G. B., Kabiri, K., Bouhendi, H., Bakhshi, H., 2013. Copolymers of glycidyl methacrylate and octadecylacrylate: synthesis, characterization, swelling properties, and reactivity ratios. Designed Monomers and Polymers, 16(1), 79–88.
• Ergen, Z., 2006. Asetil benzofuran metakrilat, homo ve kopolimerlerinin sentezi ve özelliklerinin incelenmesi. Yüksek Lisans Tezi, Fırat Üniversitesi Fen Bilimleri Enstitüsü, Elazığ, 64.
• Finemann, M., Ross, S.D., 1950. Linear method for determining monomer reactivity ratios in copolymerization. Journal of Polymer Science, 5, 259–262.
• Gruber, J. And Li, R.W.C., 1997. Electrochemical syntheses of poly(4,7-benzofuran vinylene) (PBFV) and poly(4,7-benzothiophene vinylene) (PBTV). Synthetic Metal, 88, 201-204.
• Ho, B.C., Lee, Y.D. and Chin, W.K., 1992. Thermal degradation of polymethacrylic acid. Journal of Polymer Science Part A: Polymer Chemistry, 30, 2389-2397.
• İlter, Z., Alhanlı, F., Yılmaz, S., 2017. Poli[2-(p-brom fenil) 1,3-dioksalan-4-il] metil akrilat kopolimerlerinin sentezi, karakterizasyonu ve fiziksel özellikleri. Erzincan Üniversitesi Journal of Science and Technology, 10(1), 23-37.
• İlter, Z., Soykan, C., Solmaz, A., 2015. Copolymers of 7-methoxy-2-acetyl benzofuryl methylmethacrylate with styrene: synthesis, characterization, reactivity ratios and determination of kinetic parameters with thermogravimetric analysis. Journal of Macromolecular Science, Part A Pure and Applied Chemistry, 52, 175-185.
• Kawaguchi, H., 2000. Functional polymer microspheres. Progress In Polymer Science, 25, 1171–1210.
• Kaya, E., 2016. 2-Hidroksietil metakrilat (HEMA) ile n-ftalimidometil metakrilat (PHMMA) 'ın serbest radikal kopolimerizasyonu: termal analiz çalışmaları ve monomer reaktiflik oranlarının belirlenmesi. Journal of Anatolian Chemistry and Chemical Education Research, 1(1), 30-43.
• Khan, M.W., Alam, M.J., Rashid, M.A., Chowdhury, R., 2005. A new structural alternative inbenzo[b] furans for antimicrobial activity. Bioorganic & Medicinian Chemistry, 13, 4796-4805.
• Kumar, H., Kumar, A., Siddaramaiah., 2006. Physico-mechanical, thermal and morphological behaviour of polyurethane / poly(methylmethacrylate) semi-interpenetrating polymer Networks. Polymer Degradation and Stability, 91, 1097-1104.
• Mar’in, A., Greci, L., Dups, P., 2002. Antioxidative activity of 3-aryl-benzofuran-2-one stabilizers (Irganox® HP-136) in polyprophylene. Polymer Degradation and Stability, 76, 489-494.
• Masubuchi, M., Eblike, H., Kawasaki, E., Sogabe, S., Morikami, K., 2003. Synthesis and biological activities of benzofuran antifungal agent star geting fungal N-myristoyl transferase. Biyoorganic &Medicinal Chemistry, 11, 4463-4478.
• Masubuchi, M., Kawasaki, K., Ebiike, H., Ikeda, Y., Tsujii, S., Sogabe, S., Fujii, T., Sakata, K., Shiratori, Y., Aoki, Y., Ohtsuka, T., Shimma, N., 2001. Design and synthesis of novel benzofurans as a new class of antifungal agent star geting fungal N-myristoyl transferase. Part 1 Bioorganic & Medicinal Chemistry Letters, 11(14), 1833-1837.
• Mizoguchi, K., Hasegawa, E., 1996. Photo active polymers applied to advanced micro electronic devices. Polymers for Advanced Technologies, 7, 471‐477.
• Song, D.M., Jung, K.H., Moon, J.H., Shin, D.M., 2002. Photo chemistry of chalcone and the application of chalcone‐derivatives in photo‐alignment layer of liquid crystal display. Optical Materials, 21, 667‐671.
• Taylor, J. W., Winnik, M. A., 2004. Functional latex and thermoset latex films. Journal of Coating Technology and Research, 1, 163–193.
• Tüdös, F., Kelen, T., Turcsanyi, B., Kennedy, J. P., 1981. Analysis of the linear methods for determining copolymerization reactivity ratios. VI. A comprehensivecriticalre examination of oxoniumion copolymerizations. Journal of Polymer Science, 19, 1119–1132.
• Vejani, C., Bellantone, R.A., 2015. An in situ method to quantitatively determine dissolved free drug concentrations in vitro in the presence of polymer excipients using pulsatile microdialysis (PMD). International Journal of Pharmaceutics, 496 (2), 275-81.
• Vinh, T.K., Ahmadi, M., Delgado, P.O.L., Perez, S.F., Walters, H.M., Smith, H.J., Nicholls, P.J., Simons, C., 1999. 1-[(Benzofuran-2-yl) phenylmethyl]-triazoles and -tetrazoles-potent competitive inhibitors of aromatase. Bioorganic & Medicinal Chemistry Letters, 9(14), 2015-2108.
• Wang, E., Xiong, H., Zhou, D., Xie, Z., Huang, Y., Jing, X., Sun, X., 2014. Co-delivery of oxali platin and demethylcantharidinvia a polymer–drug conjugate. Macromolecular Bioscience, 14(4), 588-96.
• Xu, J.K., Nie, G.M., Zhang, S.S., Han, X.J., Pu, S.Z., Shen, L., Xiao, Q., 2005. Electro syntheses of poly(2,3-benzofuran) films in boron trifluoride diethylether ate containing poly(ethyleneglycol) oligomers. European Polymer Journal, 41(7), 1654-1661.
• Xue, J.T., McKinney, M. A., Wilkie, C. A., 1997. The thermal degradation of poly acrylonitrile. Polymer Degradation and Stability, 58, 193-2002.
• Yoruç, A.B.H., Uğraşkan, V., 2017. Yeşil Polimerler ve Uygulamaları. Afyon Kocatepe Üniversitesi Afyon Kocatepe University Journal of Science and Engineering, 17, 318-337.
• Zhang, L.Z., Li, Y., Liang, Z.X., Yu, Q.S., Cai, Z.G., 1999. New cross linked polymer systems with high and stable optical non linearity. Reactive and Functional Polymer. 40, 255‐262.