Poly(phthalaldehyde) and its copolymers are metastable polymers that have been shown to rapidly depolymerize from the solid state back into their constituent monomers, a consequence of their low ceiling temperature. This rapid depolymerization upon triggering makes it well suited as a potential chemically recyclable polymer, and for niche engineering applications. Several studies will be presented on both the fundamental chemistry and engineering applications of these stimuli-responsive materials. A microflow reactor was utilized to probe the rapid, cationic polymerization kinetics of phthalaldehyde. Molecular weight and conversion data give insights into the growth mechanism of these inherently cyclic polymers. Notably, at higher conversions polymer chains start to fuse via intermolecular chain transfer reactions that results in rapid, substantial increase in the observed molecular weights. A series of phthalaldehyde-aliphatic aldehyde-based copolymers were synthesized in order to understand the reactivity behaviors of aldehyde comonomers. Electron deficient aldehydes display improved polymerizability by increasing the monomer’s electrophilicity. These rapidly degradable copolymers, whose properties can be optimized by monomer composition, show promise as resist materials for both thermal and optical lithography processes.

Synthesis of rapidly depolymerizable phthalaldehyde-based polymers and their application toward dry-develop lithography

ACS Spring 2022

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