3 years ago

Poly(Ethylene Glycol) Dimethacrylates with Cleavable Ketal Sites: Precursors for Cleavable PEG-Hydrogels

Poly(Ethylene Glycol) Dimethacrylates with Cleavable Ketal Sites: Precursors for Cleavable PEG-Hydrogels
Daniel Leibig, Hannah Pohlit, Holger Frey
The authors introduce poly(ethylene glycol) (PEG) based macromonomers containing acid-labile ketal moieties as well as terminal methacrylate units that are amenable to radical polymerization. The synthesis of PEGs of different molecular weights (ranging from 2000 to 13 000 g mol−1 with polydispersities <1.15) with a central ketal unit (PEG-ketal-diol) and their conversion to PEG-ketal-dimethacrylates (PEG-ketal-DMA) is introduced. Degradation rates of both PEG-ketal-diols and PEG-ketal-DMA are investigated by in situ 1H NMR kinetic studies in deuterated phosphate buffer. Hydrogels containing 0, 5, or 10 wt% of PEG-ketal-DMA and 100, 95, or 90 wt% of PEG-DMA, respectively, are synthesized and disintegration of the gels is investigated in buffer at different pH values. Visible disintegration of the gels appears at pH 5 for hydrogels containing PEG-ketal-DMA, whereas no visible degradation is observed at all at neutral pH or for PEG hydrogels without PEG-ketal-DMA. Poly(ethylene glycol) (PEG) based macromonomers containing acid-labile ketal moieties as well as terminal methacrylate units are synthesized and their degradation rates are investigated by in situ 1H NMR kinetic studies in deuterated phosphate buffer. Hydrogels composed of PEG-dimethacrylates and PEG-ketal-dimethacrylates are prepared and the disintegration of the gels is investigated in buffers at different pH values.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/mabi.201600532

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