Synthesis and characterization of novel biodegradable polymers composed of hydroxycinnamic acid and D,L-lactic acid

D,L -Lactic acid (DLLA) was polycondensed with 4-hydroxycinnamic acid (4HCA), a derivative of cinnamic acid, to prepare a novel functional biodegradable polymer. The polymer was prepared using two different methods, the solvent method, which used acetic anhydride as the solvent, and the direct method. White and brown-colored copolymers were obtained by these two methods, respectively. ¹H-NMR spectroscopy and UV-visible spectroscopy revealed that the double bond of 4HCA was almost completely destroyed when the copolymer was prepared by the direct method. On the other hand, copolymers in which the double bond was preserved in the 4HCA–DLLA copolymer were successfully obtained using the solvent method. The solubility of the copolymers obtained by the solvent method in organic solvent was poor. When the copolymer was prepared under a 4HCA:DLLA ratio of 20:80 using the solvent method, the resulting copolymer had high solubility in organic solvents and the double bond was preserved. Moreover, it was confirmed that the 4HCA–DLLA copolymer synthesized by the solvent method was both photoreactive and biodegradable. The 4HCA–DLLA copolymer is expected to be used as basic material for tissue engineering and drug delivery systems, in addition to applications as an orthopedic matrix and a degradable plastic. © 2001 John Wiley & Sons, Inc. J Appl Polym Sci 82: 2357–2364, 2001