Synthesis and characterization of novel biodegradable aromatic–aliphatic poly(ester amide)s containing ethylene oxide moieties

Abstract

A series of novel biodegradable aromaticaliphatic poly(ester amide)s containing approximately equal amounts of amide and ester groups were successfully prepared through the interfacial polycondensation of 1,6-hexanediamine and aromatic diacylchlorides containing ethylene oxide moieties. The structure of the poly(ester amide)s was verified by Fourier transform infrared and NMR spectra. Differential scanning calorimetry and thermogravimetric analysis measurements demonstrated that the obtained polymers were amorphous and stable up to 3008C under nitrogen. The synthesized poly(ester amide)s showed good hydrophilicity and took up water in amounts up to 50% of their weights when exposed to a humid atmosphere. Under physiological conditions, the poly(ester amide)s were hydrolysable in a rapid and steady way.

Biodegradable Aromatic–Aliphatic Poly(ester–amides) from Monolignol-Based Ester Dimers

“…The eight carbon aliphatic spacer offers flexibility and optimal spacing between the amide and ester linkages to allow for increased intermolecular and intramolecular interactions between the chains. A similar effect was seen by Wang et al in their synthesis of aromatic–aliphatic poly­(ester–amide)­s containing different length polyethylene glycol (PEG) spacers . The polymers showed increasing T g as the length of the PEG spacer increased, due to decreased molecular mobility with increased interactions.…”

“…A similar effect was seen by Wang et al in their synthesis of aromatic−aliphatic poly(ester−amide)s containing different length polyethylene glycol (PEG) spacers. 37 The polymers showed increasing T g as the length of the PEG spacer increased, due to decreased molecular mobility with increased interactions. The addition of an aromatic linker, instead of an aliphatic linker, had varied effects on the glass transition temperature.…”

Biomass-Derived Poly(ether-amide)s Incorporating Hydroxycinnamates

“…These deviations in glass transition temperature may be due increased chain interactions, which prevent polymer chain movement. Wang et al saw a similar effect in the synthesis of poly­(ether-amide)­s with polyethylene glycol spacers . The observed T g increased as the length of the polyethylene glycol spacer increased, possibly due to increased interchain interactions.…”

“…Wang et al saw a similar effect in the synthesis of poly(ether-amide)s with polyethylene glycol spacers. 28 The observed T g increased as the length of the polyethylene glycol spacer increased, possibly due to increased interchain interactions. However, it is difficult to ascribe a definitive cause to this increased T g , as the samples also likely differ in molecular weight (as discussed below).…”

Synthesis and hydrolytic degradation of stereoregular aromatic poly(ester amide)s derived from D‐xylose

“…Aromatic PEAs present resistance to heat, outstanding mechanical properties, poor biodegradability, and poor solubility in common solvents 2. Some of these properties could be limiting factors in their future applications because processable engineering plastics possessing moderately high softening temperatures and/or solubility in organic solvents are required for practical use.…”