Polímeros: Ciência e Tecnologia
https://revistapolimeros.org.br/article/doi/10.1590/0104-1428.1950
Polímeros: Ciência e Tecnologia
Scientific & Technical Article

Synthesis, characterization and thermal degradation of cross-linked polystyrene using the alkyne-functionalized esters as a cross-linker agent by click chemistry method

Akat, Hakan; Saltan, Fehmi

Downloads: 0
Views: 961

Abstract

In this study, it has been demonstrated that cross-linked polystyrene (CPS) was successfully prepared by using click chemistry. For this purpose, firstly, poly (styrene-co-4 chloromethylstyrene) with 4-chloromethylstyrene was synthesized. Secondly, alkyne-functionalized esters (dipropargyl adipate, dipropargyl succinate) were obtained using propargyl alcohol, adipoyl chloride and succinyl chloride. Azide-functionalized polystrene (PS-N3) and dipropargyl adipate (or dipropargyl succinate) were reacted in N,N-dimethylformamide for 24 h at room temperature to give CPS. The synthesized polymer and compounds were characterized by nuclear magnetic resonance (1H-NMR), gel permeation chromatography (GPC), fourier transform infrared spectroscopy (FT-IR) and thermogravimetric (TG/DTG) analysis.. The surface properties were investigated by Scanning Electron Micrography (SEM).

Keywords

polystyrene, cross-linked polymers, click chemistry, thermal degradation.

References

1. Ai, Z. Q., Zhou, Q. L., Guang, R., & Zhang, H. T. (2005). Preparation and properties of polystyrene-g-poly(butyl acrylate) copolymer emulsions with ultrasonic radiation. I. Preparation technology and coagulum ratio. Journal of Applied Polymer Science, 96(4), 1405-1409. http://dx.doi.org/10.1002/app.21571.

2. Qin, L., He, X. W., Zhang, W., Li, W. Y., & Zhang, Y. K. (2009). Surface-modified polystyrene beads as photografting imprinted polymer matrix for chromatographic separation of proteins. Journal of Chromatography. A, 1216(5), 807-814. http://dx.doi.org/10.1016/j.chroma.2008.12.007. PMid:19111313.

3. Yu, P., Li, X., Li, X., Lu, X., Ma, G., & Su, Z. (2007). Preparative purification of polyethylene glycol derivatives with polystyrene-divinylbenzene beads as chromatographic packing. Bioorganic & Medicinal Chemistry Letters, 17(20), 5605-5609. http://dx.doi.org/10.1016/j.bmcl.2007.07.094. PMid:17822896.

4. Mizutani, A., Nagase, K., Kikuchi, A., Kanazawa, H., Akiyama, Y., Kobayashi, J., Annaka, M., & Okano, T. (2010). Thermo-responsive polymer brush-grafted porous polystyrene beads for all-aqueous chromatography. Journal of Chromatography. A, 1217(4), 522-529. http://dx.doi.org/10.1016/j.chroma.2009.11.073. PMid:20015506.

5. Zhang, X., Shen, S., & Fan, L. (2007). Studies progress of preparation, properties and applications of hyper-cross-linked polystyrene networks. Journal of Materials Science, 42(18), 7621-7629. http://dx.doi.org/10.1007/s10853-007-1763-y.

6. Belfer, S., & Glozman, R. (1979). Anion exchange resins prepared from polystyrene crosslinked via a Friedel–Crafts reaction. Journal of Applied Polymer Science, 24(10), 2147-2157. http://dx.doi.org/10.1002/app.1979.070241007.

7. Jun, B. H., Byun, J. W., Kim, J. Y., Kang, H., Park, H. J., Yoon, J., & Lee, Y. S. J. (2010). Facile method of preparing silver-embedded polymer beads and their antibacterial effect. Journal of Materials Science, 45(11), 3106-3108. http://dx.doi.org/10.1007/s10853-010-4345-3.

8. Yun, Y. H., Shon, H. K., & Yoon, S. D. (2009). Preparation and characterization of molecularly imprinted polymers for the selective separation of 2,4-dichlorophenoxyacetic acid. Journal of Materials Science, 44(22), 6206-6211. http://dx.doi.org/10.1007/s10853-009-3863-3.

9. Yu, H., Cai, Z., Liu, X., Li, M., Shi, Z., & Cui, Z. (2014). Crosslinked polystyrene beads modified with polar groups for the separation of aromatic/aliphatic hydrocarbons. Journal of Applied Polymer Science, 131(8), 40156-40162. http://dx.doi.org/10.1002/app.40156.

10. Archibald, T. G., Malik, A. A., Baum, K., & Unroe, M. R. (1991). Thermally stable acetylenic adamantane polymers. Macromolecules, 24(19), 5261-5265. http://dx.doi.org/10.1021/ma00019a005.

11. Bellenger, V., Verdu, J., & Morel, E. (1989). Structure-properties relationships for densely cross-linked epoxide-amine systems based on epoxide or amine mixtures. Journal of Materials Science, 24(1), 63-68. http://dx.doi.org/10.1007/BF00660933.

12. Douglas, W. E., & Overend, A. S. (1991). Curing reactions in acetylene terminated resins—I. Uncatalyzed cure of arylpropargyl ether terminated monomers. European Polymer Journal, 27(11), 1279-1287. http://dx.doi.org/10.1016/0014-3057(91)90066-W.

13. Kirchhoff, R. A., Bruza, K., Carriere, C., & Rondan, N. (1992). Makromolekulare Chemie. Macromolecular Symposia, 54-55(1), 531-534. http://dx.doi.org/10.1002/masy.19920540140.

14. Morel, E., Bellenger, V., Bocquet, M., & Verdu, J. (1989). Structure-properties relationships for densely cross-linked epoxide-amine systems based on epoxide or amine mixtures. Journal of Materials Science, 24(1), 69-75. http://dx.doi.org/10.1007/BF00660934.

15. Yagci, Y., Kiskan, B., Gacal, B., & Ergin, M. (2007). Thermally curable polystyrene via click chemistry. Macromolecules, 40(13), 4724-4727. http://dx.doi.org/10.1021/ma070549j.

16. Wang, Y. X., & Ishida, H. (1999). Cationic ring-opening polymerization of benzoxazines. Polymer, 40(16), 4563-4570. http://dx.doi.org/10.1016/S0032-3861(99)00074-9.

17. Kasapoglu, F., Cianga, I., Yagci, Y., & Takeichi, T. (2003). Photoinitiated cationic polymerization of monofunctional benzoxazine. Journal of Polymer Science. Part A, Polymer Chemistry, 41(21), 3320-3328. http://dx.doi.org/10.1002/pola.10913.

18. Gacal, B., Akat, H., Balta, D. K., Arsu, N., & Yagci, Y. (2008). Synthesis and characterization of polymeric thioxanthone photoinitatiors via double click reactions. Macromolecules, 41(7), 2401-2405. http://dx.doi.org/10.1021/ma702502h.

19. Yildirim, Y., Dogan, B., Muğlali, S., Saltan, F., Ozkan, M., & Akat, H. (2012). Synthesis, characterization, and thermal degradation kinetic of polystyrene-g-polycaprolactone. Journal of Applied Polymer Science, 126(4), 1236-1246. http://dx.doi.org/10.1002/app.36888.

20. Malhotra, S. L., Hesse, J., & Blanchard, L. P. (1975). Thermal decomposition of polystyrene. Polymer, 16(2), 81-93. http://dx.doi.org/10.1016/0032-3861(75)90133-0.

21. Sivalingam, G., & Madras, G. (2003). Thermal degradation of poly (ε-caprolactone). Polymer Degradation & Stability, 80(1), 11-16. http://dx.doi.org/10.1016/S0141-3910(02)00376-2.

22. McNeill, I. C., Zulfiqar, M., & Kousar, T. A. (1990). Detailed investigation of the products of the thermal degradation of polystyrene. Polymer Degradation & Stability, 28(2), 131-151. http://dx.doi.org/10.1016/0141-3910(90)90002-O.
588371c57f8c9d0a0c8b4a60 polimeros Articles
Links & Downloads

Polímeros: Ciência e Tecnologia

Share this page
Page Sections