Structure-property relationships of degradable polyurethane elastomers containing an amino acid-based chain extender

Abstract

A series of degradable polyurethanes of variable soft segment chemistry and content were synthesized and characterized. An amino acid-based diester chain extender was used to confer degradability and both polycaprolactone diol (PCL) and polyethylene oxide (PEO) were used as soft segments. In addition, the diisocyanate component was a potentially nontoxic diisocyanate (2,6-diisocyanato methyl caproate, LDI). The physicochemical properties of these unique series of polyurethanes were investigated. It was found that the PEO containing polyurethanes were generally weak, tacky amorphous materials. In contrast, the PCL polyurethanes were relatively strong, elastomeric materials which ranged from completely amorphous to semicrystalline as noted by differential scanning calorimetry. The PCL containing polyurethanes exhibited increasing tensile strength, modulus, and ultimate strain with increasing PCL molecular weight because of increasing phase separation and increasing soft segment crystallinity. Fourier transform infrared analysis showed significant hard segment urea and urethane hydrogen bonding which increased with hard segment content, although interphase bonding is believed to be significant for the PCL polyurethanes. Surface characterization carried out by contact angle analysis and X-ray photoelectron spectroscopy indicated soft segment surface enrichment for all of the polyurethanes. The PEO-based polymers were very hydrophilic whereas the PCL-based polymers displayed significantly higher contact angles, indicating greater surface hydrophobicity. The observed diversity in material properties suggests that these polyurethanes may be useful for a wide range of applications. © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 75: 1522–1534, 2000