Fabrication of thin‐film composite membranes with pendant, photoreactive diazoketone functionality

A disulfonyl chloride monomer having a pendent photoreactive diazoketone functional group has been synthesized in high overall yield (>90%). The synthesis involves a convenient two‐step reaction sequence starting from commercially available 6‐diazo‐5‐oxo‐5,6‐dihydro‐1‐naphthalenesulfonyl chloride, which was reacted with piperazine then 1,3,6‐naphthalenetrisulfonyl chloride to give the disulfonyl chloride diazoketone. Thin‐film composite membranes having photoreactive diazoketone moieties as side chains of a polysulfonamide have been successfully fabricated by interfacial polymerization of ethanediamine with the disulfonyl chloride diazoketone on a polysulfone support. The effect of polymerization parameters such as monomer concentration, polymerization time, crosslinking, and surfactant have been systematically investigated in terms of membrane morphology and permeation properties. © 1997 John Wiley & Sons, Inc. J Appl Polym Sci 64: 2381–2398, 1997