A New Green Catalyst for Synthesis of bis-Macromonomers of Polyethylene Glycol (PEG)

Sara Haoue1, Hodhaifa Derdar1, 2, Mohammed Belbachir1, Amine Harrane1, 3
1 Oran1 University Ahmed Benbella BP N° 1524 El M’Naouar, 31000 Oran, Algeria 2 Centre de Recherche Scientifique et Technique en Analyses Physico-Chimiques (CRAPC), BP 10 384, Siège ex-Pasna Zone Industrielle, Bou-Ismail CP 42004, Tipaza, Algeria 3 Department of Chemistry, FSEI University of Abdelhamid Ibn Badis – Mostaganem, Algeria hodhaifa-27@outlook.fr
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A new method to synthesise polyethylene glycol dimethacrylate (PEGDM) with various molecular weights (1000, 3000, 6000 and 8000 g/mol) of polyethylene glycol (PEG) has been developed. This technique consists in using Maghnite-H+ as eco-catalyst to replace еriethylamine, which is toxic. Maghnite-H+ is a proton exchanged montmorillonite clay which is prepared through a simple exchange process. Synthesis experiments are performed in solution using dichloromethane as solvent in the presence of methacrylic anhydride. The effect of reaction time, temperature, amount of catalyst and amount of methacrylic anhydride is studied in order to find the optimal reaction conditions. The synthesis in solution leads to the best yield (98 %) at room temperature for the reaction time of 5 h. The structure of the obtained macromonomers (PEGDM) is confirmed by FTIR, 1H NMR and 13C NMR, where the methacrylate end groups are clearly visible. Thermogravimetric analysis (TGA) is used to study the thermal stability of these obtained macromonomers. The presence of unsaturated end group was confirmed by UV-Visible analysis.

[1] Vilela C., Sousa A, Fonseca A. et al.: Polym. Chem., 2014, 5, 3119. https://doi.org/10.1039/c3py01213a
[2] Kricheldorf H.: Experiments Before World War I. [in:] Polycondensation. Springer, Berlin, Heidelberg 2014, 7-25. https://doi.org/10.1007/978-3-642-39429-4_2
[3] Hutanu D., Frishberg M., Guo L., Darie C.: Mod. Chem. Appl., 2014, 2, 132. https://doi.org/10.4172/2329-6798.1000132
[4] Kim J.-H., Emoto K., Lijima M. et al.: Polym. Adv. Technol., 1991, 10, 647. https://doi.org/10.1002/(SICI)1099-1581(199911)10:11<647::AID-PAT918>3.0.CO;2-Y
[5] Kim B.-S., Hrkach J.-S., Langer R.: Biomaterials, 2000, 21, 259. https://doi.org/10.1016/S0142-9612(99)00174-X
[6] Lu S., Anseth K.: Macromolecules, 2000, 33, 2509. https://doi.org/10.1021/ma9915024
[7] Madaghiele M., Salvatore L., Demitri C., Sannino A.: Mater Lett., 2017, 5, 1. https://doi.org/10.1016/j.matlet.2018.02.048
[8] Ponnuvely D., Kim S., Lee J.: Micro Nano Syst. Lett., 2018, 218, 305. https://doi.org/10.1186/s40486-017-0056-8
[9] McAvoy K., Jones D., Thakur R.: Pharm. Res., 2018, 35, 36. https://doi.org/10.1007/s11095-017-2298-9
[10] Benoit D., Anseth K.: Acta Biomater., 2001, 1, 461. https://doi.org/10.1016/j.actbio.2005.03.002
[11] Benoit D., Durney A., Anseth K.: Biomaterials, 2007, 28, 66. https://doi.org/10.1016/j.biomaterials.2006.08.033
[12] Lin-Gibson S., Bencherif S., Cooper J. et al.: Biomacromolecules, 2004, 5, 1280. https://doi.org/10.1021/bm0498777
[13] Hensen K., Mahaim C., HiSlderich W.: Appl. Catal. A-Gen., 1997, 149, 311. https://doi.org/10.1016/S0926-860X(96)00273-6
[14] Seghier S., Belbachir M.: Iran J. Sci. Technol. Trans. Sci., 2018, 3, 1. https://doi.org/10.1007/s40995-018-0629-2
[15] Derdar H., Belbachir M., Harrane A.: BCREC, 2018, in press. https://doi.org/10.9767/bcrec.0.0.2692.xxx-xxx
[16] Belbachir M., Bensaoula A.: Pat. US 066969 0101, 2001.
[17] Belbachir M., Bensaoula A.: Pat. US 7, 094, 823 B2, 2006.
[18] Hennaoui F., Belbachir M.: J. Macromol. Sci. A, 2015, 52, 992. https://doi.org/10.1080/10601325.2015.1095602
[19] Baghdadli M., Meghabar R., Belbachir M.: Asia J. Chem., 2016, 28, 1197. http://doi.org/10.14233/ajchem.2016.19620
[20] Draoua Z., Harrane A., Belbachir M.: J. Macromol. Sci. A., 2015, 52, 130. https://doi.org/10.1080/10601325.2015.980763
[21] Derdar H., Belbachir M., Hennaoui F. et al.: Polym. Sci. B, 2018, 60, 555. https://doi.org/10.1134/S1560090418050056
[22] Gorniak K., Szydlak T., Gawel A.: Appl. Clay Sci., 2017, 141, 180. https://doi.org/10.1016/j.clay.2017.02.032
[23] Simon G., Allen P., Wiliams D.: Polymer, 1991, 32, 2577. https://doi.org/10.1016/0032-3861(91)90337-I
[24] Yahiaoui A., Belbachir M.: J. Appl. Polym. Sci., 2006, 100, 1681. https://doi.org/10.1002/app.22946