Organic acids catalyzed polymerization of ε‐caprolactone: Synthesis and characterization

Abstract

Environmentally friendly organocatalytic synthesis of aliphatic polyesters was studied. The catalysis investigated is novel, and lends itself well to the potential production of valuable biodegradable products. The reactions were based on an organic acids-catalyzed ring-opening polymerization of e-caprolactone with fatty acid derivatives as the initiator and were performed in the absence of solvents. The chemical structures of the functionalized polymers were confirmed by 1 H and 13 C-NMR spectra. Polymers with different molecular weights, in the range 10,900-15,200 were obtained in the presence of fumaric acid as catalyst. The thermal properties of the functionalized PCLs were determined by modulated differential scanning calorimetry and thermogravimetric analysis. The MDSC results verified that the crystallinity and the melting point of the lipid-functionalized polymers were lower than that of the unfunctionalized poly(e-caprolactone). The hydrolytic degradation of the functionalized polymer was also investigated. The result shows the degradation rate was affected by the presence of oleic acid derivatives in the polymer molecule. The lipid-functionalized polymers synthesized by the metalfree polymerization systems seem to be suitable biodegradable polyesters for use in biomedical and pharmacological applications.

Effect of ionic liquids on the structural, thermal, and in vitro degradation properties of poly(ε‐caprolactone) synthesized in the presence of Candida antarctica lipase B

“…The polymers synthesized in ILs showed bimodal melting peak (Figure ). These results indicated that the imperfect crystallization existed in the synthesized samples, probably because of the presence of cyclic macromolecules in the structure of the synthesized polymers. Furthermore, these results are well correlated with those obtained from NMR, MALDI‐TOF and SEC/MALLS studies, regarding the evidence of multiphase morphology of PCLs.…”

Synthesis and Properties of a Star-Shaped Poly( ϵ -Caprolactone)–Ibuprofen Conjugate

“…However, the drug within the body cannot be released from the delivery matrix before degradation of the polymer [64]. Our previous study of linear PCL demonstrated a weight loss of 2.0% after 16 days of hydrolytic degradation [65]. In this work, the hydrophilicity and physicochemical properties of the obtained polymers were improved due to the presence of the PA-MAM dendrimer in the macromolecule.…”

A polycaprolactone‐based compatibilization treatment to improve dispersion and interphase structure of silica polyurethane composites

“…This is an essential aspect so as to avoid silica aggregation and a subsequent effect in the grafting kinetics . It should be noticed that there are several ways to describe how the grafting process covers the silica surface ; however, in this work we will use the organic weight fraction of the GN as the main parameter. This is obtained using TGA analysis, where it is possible to discern the inorganic (silica) and organic (grafted caprolactone) weight fractions.…”