Responsive Polyesters with Alkene and Carboxylic Acid Side-Groups for Tissue Engineering Applications

Abstract

Main chain polyesters have been extensively used in the biomedical field. Despite their many advantages, including biocompatibility, biodegradability, and others, these materials are rather inert and lack specific functionalities which will endow them with additional biological and responsive properties. In this work, novel pH-responsive main chain polyesters have been prepared by a conventional condensation polymerization of a vinyl functionalized diol with a diacid chloride, followed by a photo-induced thiol-ene click reaction to attach functional carboxylic acid side-groups along the polymer chains. Two different mercaptocarboxylic acids were employed, allowing to vary the alkyl chain length of the polymer pendant groups. Moreover, the degree of modification, and as a result, the carboxylic acid content of the polymers, was easily tuned by varying the irradiation time during the click reaction. Both these parameters, were shown to strongly influence the responsive behavior of the polyesters, which presented adjustable pKα values and water solubilities. Finally, the difunctional polyesters bearing the alkene and carboxylic acid functionalities enabled the preparation of cross-linked polyester films by chemically linking the pendant vinyl bonds on the polymer side groups. The biocompatibility of the cross-linked polymers films was assessed in L929 fibroblast cultures and showed that the cell viability, proliferation, and attachment were greatly promoted on the polyester surface, bearing the shorter alkyl chain length side groups and the higher fraction of carboxylic acid functionalities.

Enhancing the Washing Durability and Electrical Longevity of Conductive Polyaniline-Grafted Polyester Fabrics

“…This observation reflected the elimination of short chains in the ester linkage . Simultaneously, the peaks at 725.32 cm –1 were attributed to the carbon–carbon chain of the carboxylic group on the fabric’s surface …”

“…39 Simultaneously, the peaks at 725.32 cm −1 were attributed to the carbon−carbon chain of the carboxylic group on the fabric's surface. 40 The hydrolysis of PES showed a significant weight loss of 25.36% when the NaOH concentration was raised to 21 wt %, as seen in Figure 2c. According to a past study, a weight loss from 15 to 30% could contribute to overall depreciation in stiffness, tenacity, and elongation of PES fabrics.…”

Synthesis and Characterization of Functionalized Polylactides Containing Acetal Units

“…This effect can be correlated with the presence of the pendant carboxylic acid groups that can undergo condensation or decarboxylation upon thermal heating. 47 Acid-Triggered Degradation of Functionalized Polylactides Containing Acetal Units. In our previously published work, 22 we proved that the random distribution of acetal units (27 mol %) in the polylactide chain enabled the degradation of copolymers within 72 h.…”

“…The TGA results showed that only the copolymer modified with thioglycolic acid had a lower T max compared to the nonmodified one. This effect can be correlated with the presence of the pendant carboxylic acid groups that can undergo condensation or decarboxylation upon thermal heating …”

Biodegradable Aromatic–Aliphatic Copolyesters Derived from Bis(2-Hydroxyethyl) Terephthalate for Sustainable Flexible Packaging Applications

“…In this work, we aim to develop an open-loop recycling strategy by synthesizing new types of high value-added biodegradable polymers rather than generating conventional C-rPET to address the issue of high PET-recycling cost. − For this purpose, we attempted to develop BHET-based biodegradable copolymers with excellent physical and mechanical properties that the conventional semicrystalline PET does not retain. The BHET-based biodegradable polymers were synthesized from BHET with various types of hydrophilic aliphatic carboxylic acids, including succinic acid (C4, SA), adipic acid (C6, AA), sebacic acid (C10, Seb), and dodecanedioic acid (C12, DDDA), − via a two-step melt polycondensation reaction to create aromatic–aliphatic poly­(ethylene aliphatate- co -terephthalate) random copolymers with increased biodegradability. − The representative monomer species utilized in this study are summarized in Table . The relationship between the chain structure of the aromatic–aliphatic random copolymers and their thermo-mechanical properties was investigated.…”