Poly(carbonate-ester)s of dihydroxyacetone and lactic acid as potential biomaterials

Biomacromolecules. 2011 Apr 11;12(4):977-86. doi: 10.1021/bm101342p. Epub 2011 Mar 14.

Abstract

The synthesis of new polymeric biomaterials using biocompatible building blocks is important for the advancement of the biomedical field. We report the synthesis of statistically random poly(carbonate-ester)s derived from lactic acid and dihydroxyacetone by ring-opening polymerization. The monomer mole feed ratio and initiator concentration were adjusted to create various copolymer ratios and molecular weights. A dimethoxy acetal protecting group was used to stabilize the dihydroxyacetone and was removed using elemental iodine and acetone at reflux to produce the final poly(lactide-co-dihydroxyacetone) copolymers. The characteristics of the copolymers in their protected and deprotected forms were characterized by (1)H NMR, (13)C NMR, GPC, TGA, and DSC. Hydrolytic degradation of the deprotected copolymers was tracked over an 8-week time frame. The results show that faster degradation occurred with increased carbonate content in the copolymer backbone. The degradation pattern of the copolymers was visualized using SEM and revealed a trend toward surface erosion as the primary mode of degradation.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Biocompatible Materials*
  • Calorimetry, Differential Scanning
  • Carbonates / chemistry*
  • Chromatography, Gel
  • Dihydroxyacetone / chemistry*
  • Esters
  • Lactic Acid / chemistry*
  • Magnetic Resonance Spectroscopy
  • Microscopy, Electron, Scanning
  • Polymers / chemistry*
  • Thermogravimetry

Substances

  • Biocompatible Materials
  • Carbonates
  • Esters
  • Polymers
  • Lactic Acid
  • Dihydroxyacetone