A series of multistage (pressure-sensitive/hot melt) adhesives utilizing dynamic thia-Michael bonding motifs are reported. The benzalcyanoacetate Michael acceptors used in this work undergo bond exchange under ambient conditions without external catalysis, facilitating pressure-sensitive adhesion. A key feature of this system is the dynamic reaction-induced phase separation that lends reinforcement to the otherwise weakly bonded materials, enabling weak, repeatable pressure-sensitive adhesion under ambient conditions and strong adhesion when processed as a hot melt adhesive. By using different pairs of benzalcyanoacetate cross-linking units, the phase separation characteristics of the adhesives can be directly manipulated, allowing for a tailored adhesive response.
Keywords: dynamic covalent chemistry; hot melt adhesive; phase separation; pressure sensitive adhesive; rheology; thia-Michael bonds.