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Poly(Ethylene Glycol) Dimethacrylates with Cleavable Ketal Sites: Precursors for Cleavable PEG‐Hydrogels
Author(s) -
Pohlit Hannah,
Leibig Daniel,
Frey Holger
Publication year - 2017
Publication title -
macromolecular bioscience
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.924
H-Index - 105
eISSN - 1616-5195
pISSN - 1616-5187
DOI - 10.1002/mabi.201600532
Subject(s) - self healing hydrogels , ethylene glycol , peg ratio , chemistry , polymer chemistry , methacrylate , polymerization , diol , organic chemistry , polymer , finance , economics
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 1 H 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.