Poly(ethylene terephthalate) (PET) is a widely used thermoplastic polymer with exceptional properties, making it a cornerstone in various industries. However, the extensive global demand for PET, particularly in the packaging sector, has led to significant ecological concerns due to inadequate recycling rates. This paper explores the potential of Meldrum's acid-based chain extenders as a solution to enhance PET recycling. Initially, 2,2,5-trimethyl-5-(4-vinylbenzyl)-1,3-dioxane-4,6-dione (St-MA) was synthesized, and its homopolymers were produced through free radical polymerization and characterized through 1H NMR, FTIR and TGA analyses. Dynamic interactions between recycled PET (rPET) and the synthesized chain extender (HP) in an extrusion environment was further explored, resulting in higher T g and T c for rPET when 0.5 » wt% of HP was added as a reactive chain extender. The chemical tunability of this functional ketene-based chain extender holds promise to enhance PET recycling practices. The continuous evolution of regulatory frameworks and environmental concerns may prompt the exploration of novel approaches, such as tailored Meldrum's acid-bearing chain extenders, which might have the potential to reduce the ecological consequences associated with post-consumer PET waste.