Polymerization of trans-Resveratrol via Condensation with Sebacic Acid

This work aimed to synthesize a "green" polymer from trans-resveratrol by condensation with sebacic acid. Trans-resveratrol is a polyphenol naturally synthesized in plants, presenting cardioprotective, anti -diabetes, anticancer, neural, and renal protective effects. It can be also considered a promising renewable resource monomer, due to its hydroxyl groups that can be esterified. The polymer was obtained by reacting trans-resveratrol with sebacic acid dichloride, under ambient conditions, with a reaction yield of 86.7%. The result material was characterized by nuclear magnetic resonance and Fourier transform infrared spectroscopies, thermogravimetry (TG) and differential scanning calorimetry (DSC), confirming the formation of a polyester, poly(resveratrol sebacate) PRS, with a glass transition temperature (Tg) of 34 degrees C. The TG curve of PRS presented two stages of mass loss, the first occurring between 158 and 388 degrees C, corresponding to a loss of 63.6% (decomposition of the aliphatic part), and the second stage of mass loss between 388 degrees C and 493 degrees C, corresponding to a loss of 23.5% (decomposition of the aromatic part). The polymer has potential applications for controlled resveratrol delivery, by hydrolysis of PRS, and as a biomaterial, presenting a Tg close to the temperature of human body.