, Elidrissi Abderrahman1, Aqil Mohamed1, Amyay Aicha1, Bellaouchi Reda2, Asehraou Abdeslam2, Jalal Isaad3, Tahani abdesselam41Laboratory Chemistry of Applied and Environmental, Faculty of Sciences, Mohammed Premier University, Oujda, Morocco
2Laboratory of Biochemistry and Biotechnology, Faculty of Sciences, Mohammed Premier University, Oujda, Morocco
3Faculty of Sciences and Techniques of Al Hoceima, BP 34, 32003 Ajdir, Mohammed Premier University, Morocco
4Laboratory of Physical Chemistry of Natural Resources and Environment - Department of Chemistry, Faculty of Sciences, Mohammed Premier University, Oujda, Morocco
A branched polyesters was synthesized using ethylene glycol, adipic acid and glycerol. It was characterized by FTIR, 1H and 13C-NMR, GPC, TGA/DTA. According to TGA analysis it was found that the mass loss is accomplished in two stages, the lower one was slightly distinguished in TGA. The Flynn-Ozawa-Wall method was applied for the principal reaction and the activation energies for all values of α were determined. The biodegradation process was also investigated in liquid culture media using two strains of Penicillium sp S1 and Aspergillus sp S2 which were isolated from the discharge of Oujda city (Morocco). According to the growth curves, it was found that the Penicillium sp S1 and Aspergillus sp S2 used the polyester as source of carbon. We have noted using FTIR spectra a decrease of the band intensity at δ =1170 cm-1 characteristic of the stretching vibration of C–O–C and also a decrease of the ester band group. The results obtained were compared with those of polyesters biodegradation reported in our previous work [27,28,29]. We have also proposed an enzyme degradation mechanism and hypothesis for an empirical mathematical formula giving the relationship between the thermal degradation and the biodegradation rate constant of the polyester.
| [1] | Ankur, S., Kulshrestha, Gao,W., Fu, H. and Richard, A.G, “Synthesis and characterization of branched polymers from lipase-catalyzed trimethylolpropane copolymerizations”, Biomacromolecules, 8(6). 1794-1801. May 2007.View Article PubMed |
| [2] | Mickaël, A., Stéphanie, D., Sinisa, M., Boris, E. and Véronique, N.R,“Characterization, stability and ecotoxic properties of readily biodegradable branched oligoesters based on bio-sourced succinic acid and glycerol”, Polymer Degradation and Stability. 97(10). 1956-1963. March 2012.View Article |
| [3] | Bruggeman, J.P., Bettinger, C.J., Nijst, C.L.E., Kohane, D.S. and Langer, R,“Biodegradable Xylitol Based Polymers”, Advanced Materials. 20(7). 1922-1927. 2008.View Article |
| [4] | Barret, D.G., Luo, W. and Yousaf, M.N, “Aliphatic polyester elastomers derived from erythritol and alpha, omega-diacids”, Polymer Chemistry. 1(3).296-302.January 2010. |
| [5] | Cao, H., Zheng, Y., Zhou, J., Wang, W. and Pandit, A, “A novel hyperbranched polyester made from aconitic acid (B3) and di(ethylene glycol) (A2)”. Polymer International. 60(4). 630-634. April 2011.View Article |
| [6] | Yang, Y., Lu, W., Cai, J., Hou, Y., Ouyang, S., Xie, W. and Gross, R, “Poly(oleic diacid-co-glycerol): Comparison of Polymer Structure Resulting from Chemical and Lipase Catalysis”. Macromolecules. 44(7).1977-1985. March 2011. |
| [7] | Kulshrestha , S., Bishwabhusan , S., Wei , G., Hongyong , F. and Gross, A, “Lipase Catalysis. A Direct Route to Linear Aliphatic Copolyesters of Bis(hydroxymethyl)butyric Acid with Pendant Carboxylic Acid Groups”. Macromolecules.38(8). 3205-3213. March 2005.View Article |
| [8] | Carnahan, M.A. and Grinstaff, M.W, “Synthesis and characterization of poly(glycerol-succinic acid) dendrimers”. Macromolecules .34(22). 7648-7655. September 2001.View Article |
| [9] | Stumbe, J.F. and Bruchmann, B, “Hyperbranched Polyesters Based on Adipic Acid and Glycerol”. Macromolar Rapid Communications .25(9).921-924 .March2004. |
| [10] | Wyatt, VT. and Strahan GD, “Degree of Branching in Hyperbranched Poly(glycerol-co-diacid)s Synthesized in Toluene”. Polymers . 4(1). 396-407.February 2012.View Article |
| [11] | Carnahan, MA. and Grinstaff, M.W, “Synthesis and characterization of polyether-ester dendrimers from glycerol and lactic acid”. Journal of American Chemical Society. 123 (12). 2905-2906. March 2001.View Article PubMed |
| [12] | Li, Y., Cook, WD., Moorhoff, C., Huang, W.C. and Chen, Q.Z, “Synthesis, characterization and proprieties of biocompatible poly(glycerol sebacate)”. Polymer International.62(4).534-547. April 2013. |
| [13] | Jena, K.K., Raju, K.V.S.M., Prathab, B. and Aminabhavi, T.M, “Hyperbranched Polyesters: Synthesis, Characterization, and Molecular Simulations”.J.Phys. Chem B. 111 (30). 8801-8811. June 2007.View Article PubMed |
| [14] | Kiyotsukuri, T., Kanaboshi, M. and Tsutsumi, N, “Network polyester films from glycerol and dicarboxylic acids”. Polymer International. 33(1).1-8. January 1994. |
| [15] | Tracy, Z., Bob, A., Adina, D., Steven, J. and Patrick, B, “Synthesis and Characterization of Glycerol-Adipic Acid Hyperbranched Polyesters”. Polymer. 55(20). 5065-5072. September 2014.View Article |
| [16] | Tang, J., Zhang, Z., Song, Z., Chen, L., Hou, X. and Yao, K, “Synthesis and characterization of elastic aliphatic polyesters from sebacic acid, glycol and glycerol”. European polymer journal. 42(12). 3360-3366. December 2006.View Article |
| [17] | Coneski, PN., Rao, KS. and Schoenfisch, M.H, “Degradable nitric oxide-releasing biomaterials via post-polymerization functionalization of cross-linked polyesters”. Biomacromolecules. 11 (11). 3208-3215. October 2010.View Article PubMed |
| [18] | Cao, W., Zhou, J., Mann, A., Wang, Y., Zhu, L,“Folate-functionalized unimolecular micelles based on a degradable amphiphilic dendrimer-like star polymer for cancer cell-targeted drug delivery”. Biomacromolecules. 12(7).2697-26707. Jun 2011. |
| [19] | Ifran, M. and Seiler, M, “Encapsulation using hyperbranched polymers: from research and technologies to emerging applications”. Ind.Eng.Chem.Res. 49(3).1169-1196. January 2010. |
| [20] | Lin, C. and Gitsov I “Synthesis and Physical Properties of Reactive Amphiphilic Hydrogels Based on Poly(pchloromethylstyrene) and Poly(ethylene glycol): Effects of Composition and Molecular”. Macromolecules . 43 (7). 3256-3267. March 2010.View Article |
| [21] | Shi, X., Wang, SH., Lee, I., Shen, M. and Baker, J.R, “Comparison of the internalization of targeted dendrimers and dendrimer-entrapped gold nanoparticles into cancer cells”. Biopolymers . 91(11).936-942. November 2009. |
| [22] | Ye, L., Letchford, K., Heller, M., Liggins, R., Guan, D. and Kizhakkedathu, J.N, “Synthesis and characterization of carboxylic acid conjugated, hydrophobically derivatized, hyperbranched polyglycerols as nanoparticulate drug carriers for cisplatin”. Biomacromolecules. 12(1).145-55. January (2011). |
| [23] | Chatterjee, S. and Ramakrishnan, S, “Understanding Self-Segregation of Immiscible Peripheral Segments in Pseudodendritic Hyperbranched Polydithioacetals: Formation of Improved Janus Structures”. Macro Letter. 3(9).953-957. September 2014. |
| [24] | Gao, C. and Yan, D, “Hyperbranched polymers: from synthesis to applications”. Progress in Polymer Science .29(3).183-275. March 2004. |
| [25] | Lea, A., Matthias, W. and Thomas, K,“The role of branched polyesters and their modifications in the development of modern drug delivery vehicles. role of branched polyesters and their modifications in the development of modern drug delivery vehicles”. Journal controlled release. 101(1-3).137-149. January 2005. |
| [26] | Coullerez, G., Lundmark, S., Malmstrom, E., Hult, A. and Mathieu, H.J, “ToF-SIMS for the characterization of hyperbranched aliphatic polyesters: probing their molecular weight on surfaces based on principal component analysis (PCA)”. Surface and Interface Analysis. 35(8). 693–708.August 2003.View Article |
| [27] | Benarbia, A., Elidrissi A., Bellaouchi, R. and Asehraou, A, “Polybutylene succinate preparation and Biodegradation study of cellulose and cellulose blends”. International Journal Engineering Technical Research. 3(3),348-354. March (2015). |
| [28] | Benarbia, A., Elidrissi, A., Aqil, M., Tabaght, F., Tahani, A. and Ouassini, K, “Kinetic Thermal Degradation of Cellulose, Polybutylene Succinate and a Green Composite: Comparative Study”. World Journal of Environmental Engineering.3(4). 95-110.September 2015. |
| [29] | Benarbia, A., Elidrissi, A., Ganetri, I., Touzani, R,“Synthesis, characterization and thermal degradation kinetics of Copolyesters”. J. Mater. Environ. Sci. 5(4).1262-1279. March 2014. |
| [30] | Ozawa, T., “A new method of analyzing thermogravimetric data”.Chem. Soc. Jpn. 38(11).1881-1886. 1965. |
| [31] | Flynn, J.H. and Wall, L.A, “Thermal Methods in Polymer Analysis”.Phys. Chem. 70A(6) 487-523.December 1966. |
| [32] | Zoubida SAADI. Université du Maine - U.F.R. Sciences et Techniques. 154.2008. |
| [33] | Trinh, T., Cooper, D., Marié, M. and Nicell, A, “Biodegradation of a Synthetic Co-Polyester by Aerobic Mesophilic Microorganisms”. Polymer Degradation Stability. 93(8). 1479-1485. August 2008.View Article |
| [34] | Warscheid, T. and Braams, J, “Biodeterioration of stone: a review.International Biodeterioration”. Biodegradation. 46(4).343-368. December 2000. |
| [35] | Hakkarainen, M., Karlsson, S. and Albertsson, A, “Rapid (bio)degradation of polylactide by mixed culture of compost microorganisms-low molecular weight products and matrix changes”. Polymer. 41(7). 2331-2338.March 2000.View Article |
| [36] | Pepic, D., Zagar, E., Zigon, M., Krzan, A., Kunaver, M. and Djonlagic, J, “Synthesis and characterization of biodegradable aliphatic copolyesters with poly(ethylene oxide) soft segments”. European Polymer Journal. 44(3). 904-917. March 2008.View Article |
| [37] | Soni, R., Soam, S. and Dutt, K, “Studies on biodegradability of copolymers of lactic acid, terephthalic acid and ethylene glycol”. Polymer Degradation Stability. 94(3). 432-437. March 2009.View Article |
| [38] | Wing-Hung LO,B.eng,“biodegradation of PHA and blends with synthetic polymer by soil microorganisms” thesis, Hong Kong university of science and technology.2000. |
| [39] | Marten, E., Joachim, R., Dieter, W, “Studies on the enzymatic hydrolysis of polyesters. II. Aliphaticearomatic copolyesters”. Polymer Degradation and Stability. 88(3). 371-381. June 2005.View Article |