Structural Characterization and Degradability of Poly( L ‐lactic acid)s Incorporating Phenyl‐Substituted α ‐Hydroxy Acids as Comonomers

Three types of copolymers of poly( L ‐lactic acid) (PLLA) were synthesized by direct polycondensation of L ‐lactic acid and phenyl‐substituted α ‐hydroxy acids ( L ‐phenyllactic acid and D ‐ and L ‐mandelic acids). It was found that the glass transition temperature of the copolymers comprising L ‐mandelic acid became significantly higher (from 58 to 69 °C) with increasing content of L ‐mandelic acid (from 0 to 50 mol‐%) although the M w decreased (from 87 000 to 4 000 Da). The cast films of the L ‐mandelic acid containing copolymers showed improved tensile properties compared with those of the PLLA film. This may be due to a pinning effect of the L ‐mandelic acid units on the helix formation of PLLA, although 30% of the units were racemized. The enzymatic degradability of the L ‐mandelic acid containing copolymers was much higher than that of PLLA, as analyzed with Proteinase K® originating from Tritirachium album .Synthesis of copolymers of L ‐lactic acid and phenyl‐substituted α ‐hydroxy acids.