Criteria for Quick and Consistent Synthesis of Poly(glycerol sebacate) for Tailored Mechanical Properties

Biomacromolecules. 2015 May 11;16(5):1525-33. doi: 10.1021/acs.biomac.5b00018. Epub 2015 Apr 24.

Abstract

Poly(glycerol sebacate) (PGS) and its derivatives make up an attractive class of biomaterial owing to their tunable mechanical properties with programmable biodegradability. In practice, however, the application of PGS is often hampered by frequent inconsistency in reproducing process conditions. The inconsistency stems from the volatile nature of glycerol during the esterification process. In this study, we suggest that the degree of esterification (DE) can be used to predict precisely the physical status, the mechanical properties, and the degradation of the PGS materials. Young's modulus is shown to linearly increase with DE, which is in agreement with an entropic spring theory of rubbers. To provide a processing guideline for researchers, we also provide a physical status map as a function of curing temperature and time. The amount of glycerol loss, obtainable by monitoring the evolution of the total mass loss and the DE during synthesis, is shown to make the predictions even more precise. We expect that these strategies can be applicable to different categories of polymers that involve condensation polymerization with the volatility of the reactants. In addition, we demonstrate that microwave-assisted prepolymerization is a time- and energy-efficient pathway to obtain PGS. For example, 15 min of microwave time is shown to be as efficient as prepolymerization in nitrogen atmosphere for 6 h at 130 °C. The quick synthesis method, however, causes a severe evaporation of glycerol, resulting in a large distortion in the monomer ratio between glycerol and sebacic acid. Consequently, more rigid PGS is produced under a similar curing condition compared to the conventional prepolymerization method. Finally, we demonstrate that the addition of molecularly rigid cross-linking agents and network-structured inorganic nanoparticles are also effective in enhancing the mechanical properties of the PGS-derived materials.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocompatible Materials / chemical synthesis*
  • Biocompatible Materials / chemistry
  • Biodegradable Plastics / chemical synthesis
  • Biodegradable Plastics / chemistry
  • Decanoates / chemical synthesis*
  • Decanoates / chemistry
  • Glycerol / analogs & derivatives*
  • Glycerol / chemical synthesis
  • Glycerol / chemistry
  • Materials Testing
  • Mechanical Phenomena
  • Polymers / chemical synthesis*
  • Polymers / chemistry
  • Tensile Strength

Substances

  • Biocompatible Materials
  • Biodegradable Plastics
  • Decanoates
  • Polymers
  • poly(glycerol-sebacate)
  • Glycerol