Novel thermally degradable diepoxy crosslinkers containing sulfonate ester groups for photo-crosslinking

Abstract New diepoxy crosslinkers (Cr-1, Cr-2 and Cr-3) containing thermally degradable sulfonate ester linkages were synthesized and characterized. From FT-IR and UV spectroscopic experiments, it was confirmed that Cr-1 and Cr-2 photochemically generated sulfonic acid, while Cr-3 was photochemically stable. Cr-1 and Cr-2 initiated photo-crosslinking reaction with poly(vinylphenol) (PVP), a copolymer of methacrylic acid and ethyl methacrylate (P(MAA-EMA)), and poly(7-oxabicyclo[4.1.0]hept-3-yl)methyl p-styrenesulfonate) (POHMSS). After irradiation at 254 nm, the Cr-1 or Cr-2/polymer blended film became insoluble and the degree of insolubilisation increased with baking at 100–140 °C. Solubilisation due to decrosslinking was observed by baking at higher temperatures (150–200 °C). The crosslinker/POHMSS system showed high efficiency in photo-thermal crosslinking and thermal decrosslinking at high temperatures.