Cost‐effective synthesis of polyricinoleate: Investigation of coating characteristics,in vitrodegradation, and antibacterial activity

Abstract

Ricinoleic acid (RA) is a component of various bio‐based copolymers. However, high‐molecular weight polyricinoleate homopolymers are not widely investigated due to high cost of commercial monomer and catalysts. In this work, we present low‐cost approach for the synthesis of high‐molecular‐weight polyricinoleate by preparing large amount of pure monomer and use of lipozyme TL IM as catalyst. First, polymerization conditions were optimized and comparative studies of medium‐molecular‐weight polyricinoleate (PRA‐M) of Mw = 30 000 gmol−1 and high‐molecular‐weight polyricinoleate (PRA‐H) of Mw = 72 000 gmol−1 were conducted. Polyricinoleates were characterized by common spectroscopic, chromatographic, and thermal methods. Solvent casting of polyricinoleates resulted in thin and continuous coating with perfectly smooth surface under SEM observation. AFM analysis of PRA films showed that surface roughness decreased with increasing molecular weight of polyricinoleate (roughness PRA‐M = 68.39 nm and PRA‐H = 57.36 nm). Degradation studies under in vitro conditions showed that both PRA‐M and PRA‐H showed good stability with only ~2% of mass loss after 6 months, possibly due to its hydrophobic nature and relatively high‐molecular weight. In contrast to RA, PRA‐M and PRA‐H do not have significant antibacterial effect on Staphylococcus aureus and Escherichia coli. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 48172.

Biobased Unsaturated Polyesters Containing Castor Oil-Derived Ricinoleic Acid and Itaconic Acid: Synthesis, In Vitro Antibacterial, and Cytocompatibility Studies

“…The surfactant behavior of ricinoleic acid moiety, because of the presence of long lateral hydrophobic methylene units in its structure, could enable permeability of the polyester into the cell membrane and inhibited the growth of bacteria . Also, the electron-deficient nature of CC bond in the itaconic acid moiety compliments the enhanced antibacterial activity of the synthesized polyesters . The plausible mechanism could be that these interactions of the bioactive monomers would cause denaturation and coagulation of bacterial proteins, thus leading to cell membrane rupture and finally cell death …”

“…62 Also, the electron-deficient nature of CC bond in the itaconic acid moiety compliments the enhanced antibacterial activity of the synthesized polyesters. 63 The plausible mechanism could be that these interactions of the bioactive monomers would cause denaturation and coagulation of bacterial proteins, thus leading to cell membrane rupture and finally cell death. 64 The antibacterial activity of representative polyester IRDd was tested on P. aeruginosa, and it showed no antibacterial activity against this Gram-negative bacterium.…”

Development of a GC-FID method for the quantitative determination of polyglycerol polyricinoleate (PGPR) in foods

“…hydroxylated) and non-polar FAMEs using a previously described (Marmesat et al 2008) two steps silica SPE method. As the hydroxy compounds do not elute easily from the GC column, resulting in the formation of broad peaks, the polar fraction was analysed after silylation (Tonta et al 2019). Figure 3(c) shows that all the non-OH FAMEs were absent in the polar fraction after the SPE procedure.…”

Analytics and applications of polyglycerol polyricinoleate (PGPR)—Current research progress

“…The detailed preparation process of PGPR and the advantages and disadvantages of various production methods have been reviewed by Bastida-Rodríguez et al (2013), Christiansen (2014), and Mortensen et al (2017). However, as long reaction times and high operating temperatures can adversely affect the quality of the final product due to the formation of side products (cyclic esters) and artifacts (coloration and odors), several studies have recently focused on the synthesis of polyricinoleic acid or PGPR using chemical (such as tin(II) 2-ethylhexanoate) or enzymatic catalysts (via immobilized or soluble enzymes, such as lipozyme TLIM, rhizopus oryzae lipase, candida rugosa lipase, and candida antarctica lipase A) in a more gentle way (Arslan et al, 2020;Ortega et al, 2013;Ortega-Requena et al, 2014;Potula et al, 2014;Tonta et al, 2019;Vadgama et al, 2019).…”