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Synthesis of an Acid‐Labile Diacrylate Crosslinker for Cleavable Michael Addition Networks
Author(s) -
Mather Brian D.,
Williams Sharlene R.,
Long Timothy E.
Publication year - 2007
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.200700221
Subject(s) - michael reaction , ethylene glycol , polymer chemistry , chemistry , catalysis , reactivity (psychology) , acrylic acid , organic chemistry , polymer , copolymer , medicine , alternative medicine , pathology
A novel acid‐cleavable diacrylate crosslinker, DCDA, was used as a difunctional Michael acceptor in the synthesis of acid‐cleavable crosslinked networks via base‐catalyzed Michael addition of telechelic poly(ethylene glycol) bis(acetoacetate). Michael addition networks containing DCDA were degraded in the presence of catalytic quantities of acids to form soluble polymeric products. Michael addition networks of non‐degradable diacrylate crosslinkers were chemically unchanged under identical reaction conditions and remained insoluble. Thermal degradation of DCDA‐containing networks was also investigated using TGA, which confirmed the thermal reactivity and concentration of the acid‐labile crosslink points.