Biocompatible Polymers from Renewable Sources: Linear Polyesters from Seed Oils of Flax and Hemp N. Galotto Galotto, L. Boggioni Istituto per lo Studio delle Macromolecole, Consiglio Nazionale delle Ricerche via Bassini 15, 20133 Milano (Italy) e-mail: boggioni@ismac.cnr.it, nella.galotto@ismac.cnr.it ABSTRACT Currently, most of the thermoplastic polymers are derived almost exclusively from petroleum derivatives. However, given the prospect of a future depletion of fossil raw materials, whose price continues to increase, the need to switch to alternative raw materials derived from renewable sources is a desirable long-term prospect. Between the renewable raw materials also vegetable oils have attracted the attention of the scientific community, for its low environmental impact, inherent biodegradability, low toxicity, the availability of large-scale and low market price. There are two characteristics that make the vegetable oils used on an industrial scale: the long aliphatic chains and the two functional groups, the double bond and the carbonyl group, very interesting for the preparation of thermoplastic materials. Among the various methods of polymerization of the vegetable oils, the polymerization by means of an acyclic diene metathesis (ADMET) seems to be the most promising. This technique allows the union of more units of ?, ?-dienes, thanks to the action of a "Grubbs" ruthenium catalyst. The objective of the project is the synthesis and polymerization of building blocks obtained from oleic acid, present in abundance in the seeds of Cannabis Sativa and Linum Usitatissimum, to obtain a polymer starting from renewable sources, biocompatible and/or biodegradable and environmentally friendly. The methyl oleate was converted by ethenolysis reaction, using first and second generation Grubbs catalysts, in the methyl-9-decenoate, subsequently transformed and reacted with diols (OH-(CH2)n-OH) of variable length. The ?,?-dienes obtained were characterized by 13C and 1H NMR spectroscopy to determine the structure and subsequently polymerized. The polymers obtained were characterized by 13C and 1H NMR spectroscopy. The molecular characterization, by Gel Permeation Chromatography (GPC), has determined values of Mn and Mw between 14000 and 86000 Da. Thermal analysis DSC showed melting point very similar for all the polymers obtained (Tc = 67° C) and crystallization point about Tm = 58° C. Riferimenti bibliografici [1]S. Warwel, et al., Chemosphere, 43, 39 (2001). [2](a) Y. Schrodi, T. Ung, A. Vargas, G. Mkrtumyan, L. C. Woo, T. M. Champagne, R. L. Pederson, S. H. Hong, Clean, 36, 669 (2008). (b) K. A. Burdett, L. D. Harris, P. Margl, B. R. Maughon, T. Mokhtar-Zadeh, P. C. Saucier, E. P. Wasserman, Organometallics, 23, 2027 (2004). [3]K. B. Wagener, J. M. Boncella, J. G. Nel, R. P. Duttweiler, M. A. Hillmyer, Macromolecules, 191, 365 (1990). [4]T. M. Trnka, R.H. Grubbs, The Development of L2X2Ru=CHR Olefin Metathesis Catalysts: An Organometallic Success Story, Acc. Chem. Res. 34, 18 (2001).
Biocompatible Polymers from Renewable Sources: Linear Polyesters from Seed Oils of Flax and Hemp
Nella Galotto Galotto;Laura Boggioni
2015
Abstract
Biocompatible Polymers from Renewable Sources: Linear Polyesters from Seed Oils of Flax and Hemp N. Galotto Galotto, L. Boggioni Istituto per lo Studio delle Macromolecole, Consiglio Nazionale delle Ricerche via Bassini 15, 20133 Milano (Italy) e-mail: boggioni@ismac.cnr.it, nella.galotto@ismac.cnr.it ABSTRACT Currently, most of the thermoplastic polymers are derived almost exclusively from petroleum derivatives. However, given the prospect of a future depletion of fossil raw materials, whose price continues to increase, the need to switch to alternative raw materials derived from renewable sources is a desirable long-term prospect. Between the renewable raw materials also vegetable oils have attracted the attention of the scientific community, for its low environmental impact, inherent biodegradability, low toxicity, the availability of large-scale and low market price. There are two characteristics that make the vegetable oils used on an industrial scale: the long aliphatic chains and the two functional groups, the double bond and the carbonyl group, very interesting for the preparation of thermoplastic materials. Among the various methods of polymerization of the vegetable oils, the polymerization by means of an acyclic diene metathesis (ADMET) seems to be the most promising. This technique allows the union of more units of ?, ?-dienes, thanks to the action of a "Grubbs" ruthenium catalyst. The objective of the project is the synthesis and polymerization of building blocks obtained from oleic acid, present in abundance in the seeds of Cannabis Sativa and Linum Usitatissimum, to obtain a polymer starting from renewable sources, biocompatible and/or biodegradable and environmentally friendly. The methyl oleate was converted by ethenolysis reaction, using first and second generation Grubbs catalysts, in the methyl-9-decenoate, subsequently transformed and reacted with diols (OH-(CH2)n-OH) of variable length. The ?,?-dienes obtained were characterized by 13C and 1H NMR spectroscopy to determine the structure and subsequently polymerized. The polymers obtained were characterized by 13C and 1H NMR spectroscopy. The molecular characterization, by Gel Permeation Chromatography (GPC), has determined values of Mn and Mw between 14000 and 86000 Da. Thermal analysis DSC showed melting point very similar for all the polymers obtained (Tc = 67° C) and crystallization point about Tm = 58° C. Riferimenti bibliografici [1]S. Warwel, et al., Chemosphere, 43, 39 (2001). [2](a) Y. Schrodi, T. Ung, A. Vargas, G. Mkrtumyan, L. C. Woo, T. M. Champagne, R. L. Pederson, S. H. Hong, Clean, 36, 669 (2008). (b) K. A. Burdett, L. D. Harris, P. Margl, B. R. Maughon, T. Mokhtar-Zadeh, P. C. Saucier, E. P. Wasserman, Organometallics, 23, 2027 (2004). [3]K. B. Wagener, J. M. Boncella, J. G. Nel, R. P. Duttweiler, M. A. Hillmyer, Macromolecules, 191, 365 (1990). [4]T. M. Trnka, R.H. Grubbs, The Development of L2X2Ru=CHR Olefin Metathesis Catalysts: An Organometallic Success Story, Acc. Chem. Res. 34, 18 (2001).I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
