Tailor‐made unsaturated poly(ester‐ amide) network that contains monomeric lactate sequences

Abstract

A novel unsaturated poly(ester‐amide) network (UPEAN) that contains isolated CC double bonds, monomeric lactate sequences, rigid benzyl side‐groups, amide groups and crosslinking points has been designed and synthesized. The structure of the intermediate and UPEAN was verified with Fourier transform infrared spectroscopy. Pores in UPEAN generated in situ were examined with scanning electron microscopy. Differential scanning calorimetry analysis shows that UPEAN is amorphous and its glass transition temperature is around 34 °C. It is found that UPEAN exhibits thermosensitive shape‐recovery characteristics. The maximum percentage weight loss of UPEAN is 10 and 42% after immersing the samples in active sludge at ambient temperature for 146 days and in 0.1 mol L−1 phosphate‐buffer saline at 37 °C for 103 days, respectively, which suggests that UPEAN is degradable. Copyright © 2007 Society of Chemical Industry

Elastomeric polyamide biomaterials with stereochemically tuneable mechanical properties and shape memory

“…We discovered that all formulations displayed shape memory behaviour (Supplementary Tables 1 and 2), a rare phenomenon in polyamides that has previously only been observed in thermoset materials 24,69 . An important note to make is that these thermoplastics display good initial shape recovery, on par with cross-linked materials containing permanent net-points which help promote their original shape structures.…”

“…Synthetic heteroatom-containing polymers featuring stereocontrolled unsaturated moieties along the main chain are not very abundant. Nonetheless, polyesters or poly(ester-amide)s [22][23][24] , prepared with pre-defined stereochemical units, such as fumaric acid, have garnered attention as biomaterials [25][26][27][28][29][30][31][32][33][34] . However, maleate-based materials have been notoriously hard to prepare due to isomerization issues 35,36 and, with the exception of a recent report 37 , only low-molecular-weight polymers have been isolated 38,39 , which reduces the durability of the materials.…”

Degradable Poly(ester amide)s for Biomedical Applications

“…Polymers were hydrolyzable in a rapid and steady way, increasing the rate of hydrolytic degradation by increasing the number of ether linkages per repeat unit. An unsaturated dicarboxylic-terminated oligoester was prepared by reaction of ethylene glycol lactate diol with maleic anhydride [71]. The oligoester was then melt-polycondensed with toluene-2,4-diisocyanate to render a crosslinked resin with unsaturated double bonds ( Figure 17).…”