A comparison of adhesive polysulfides initiated by garlic essential oil and elemental sulfur to create recyclable adhesives

Abstract

Despite adhesives having their origins in natural materials, most glues are formed from petroleum-based products. However, many natural adhesives lack the strength to compete with synthetic glues. Therefore, strong, sustainable alternatives are needed. Data presented here build on prior work that combines elemental sulfur, a petroleum byproduct, and garlic essential oil (GEO) which is composed of allyl sulfides, to make adhesives. Here, we have demonstrated that both sulfur and GEO can initiate polymerization at 160 °C with another petroleum byproduct, dicyclopentadiene, and a variety of natural monomers through the formation of sulfur radicals. In addition to using natural monomers and petroleum byproducts, these processes are solvent free and have high atom economy, limiting waste formation, and meeting many principles of green chemistry. Much of this work has focused on determining the effect of each sulfur source on polymerization and adhesion. A family of polymers were created with varied S : GEO : monomer ratios and characterized to determine differences in their chemical and materials properties. Despite similarities in the reaction mechanism, sulfur tends to polymerize more rapidly and create materials that are more ductile and more easily reprocessed. GEO is slower to react causing more polymerization to take place on the adherend surface yielding a more brittle polymer with higher maximum adhesion strength but lower work of adhesion. Both polymers exhibited effective adhesive recyclability. Overall, a combination of natural oils and petroleum byproducts were combined to make inexpensive, sustainable, recyclable adhesives.