Synthesis, characterization, and hydrolytic degradation of biodegradable poly(ether ester)‐urethane copolymers based on ε‐caprolactone and poly(ethylene glycol)

Abstract

In this article, a new kind of biodegradable poly(e-caprolactone)-poly(ethylene glycol)-poly(e-caprolactone)-based polyurethane (PCEC-U) copolymers were successfully synthesized by melt-polycondensation method from e-caprolactone (e-CL), poly(ethylene glycol) (PEG), 1,4-butanediol (BD), and isophorone diisocyanate (IPDI). The obtained copolymers were characterized by 1 H-nuclear magnetic resonance ( 1 H-NMR), FTIR, and gel permeation chromatography (GPC). Thermal properties of PCEC-U copolymers were studied by DSC and TGA/DTG under nitrogen atmosphere. Water absorption and hydrolytic degradation behavior of these copolymers were also investigated. Hydrolytic degradation behavior was studied by weight loss method.1 H-NMR and GPC were also used to characterize the hydrolytic degradation behavior of PCEC-U copolymers. The molecular weight of PCL block and PEG block in soft segment and the content of hard segment strongly affected the water absorption and hydrolytic degradation behavior of PCEC-U copolymers.

Electrospun biodegradable calcium containing poly(ester‐urethane)urea: Synthesis, fabrication, in vitro degradation, and biocompatibility evaluation

“…After 6 months of incubation time the scaffold lost 25% of its original mass. Similar trend was observed for L ‐tyrosine, PCL, and HDI‐based polyurethane, which showed a mass loss of 13% after 2 months of in vitro degradation 4. The hydrolytic degradation of polyurethane urea usually proceeds by the scission of urethane, urea, and ester bonds in the main chain.…”

“…Similar trend was observed for L-tyrosine, PCL, and HDI-based polyurethane, which showed a mass loss of 13% after 2 months of in vitro degradation. 4 The hydrolytic degradation of polyurethane urea usually proceeds by the scission of urethane, urea, and ester bonds in the main chain. In PEUU, in addition to this, dissociation of ionic groups in the chain extender can also occur.…”

“…To overcome these problems several groups have incorporated more hydrophilic and easily degradable soft segment materials into polyurethane, like the introduction of polyethylene glycol along with PCL. [2][3][4][5][6] Alternatively the chemistry of hard segment can be varied to influence the in vitro degradation rate of the polyurethane. Skarja and Woodhouse have introduced an amino acid based chain extender, which act as hydrolysable hard segment.…”

Preparation of waterborne elastic polyesters by chain extension with isophorone diisocyanate as a chain extender

“…In Figure (c), H signals from EPET50 sample were the total contributions of the soft and hard segments, and no new peaks were found distinctly. The reason for this is that the weak peaks of urethane group of the carbamate linker are not always observed, and also because these peaks, as shown in Figure (c), were overlapped with those of the soft or hard segment polyesters …”

Study of Biological Degradation of New Poly(Ether-Urethane-Urea)s Containing Cyclopeptide Moiety and PEG by Bacillus amyloliquefaciens Isolated from Soil

“…A high molecular weight polymer is primarily oxidized or hydrolyzed by enzymes to functional groups which improve the polymer hydrophilicity. Then, the polymer is depolymerized by microbial enzymes and then absorbed by microbial cells and ruined [10][11][12][13]. Biodegradability of PUs is generally achieved by incorporating labile and hydrolyzable moieties into the polymer backbone.…”