Synthesis of novel biodegradable polyanhydrides containing aromatic and glycol functionality for tailoring of hydrophilicity in controlled drug delivery devices

Aromatic diacids were synthesized from chlorinated triethylene or pentaethylene glycols and p-hydroxy benzoic acid. The diacids were acetylated with acetic anhydride to produce homopolymers of polyanhydrides for controlled release applications such as the stabilization of proteins and drugs. Adding ethylene glycol segments into the acid monomer allows tailoring of the hydrophobicity of the polyanhydrides, which in turn dictates the solubility of molecules within the polymer matrix and degradation rate of the polymer. The glycol containing polyanhydrides were characterized by NMR, GPC, DSC and dissolution testing. The release characteristics and mechanism of the new polyanhydrides were evaluated using hydrophilic and hydrophobic dyes.