Evaluation of 3-Allyl-5-vinylveratrole in Latex Copolymerization with an Acrylic Monomer from High Oleic Soybean Oil

Renewable 3-allyl-5-vinylveratrole (AVV) has been evaluated and classified as a biobased cross-linkable vinyl monomer in free-radical chain polymerization. AVV can be readily synthesized in four steps from vanillin, a compound available from lignin. Retained during macromolecular backbone formation, allylic unsaturation can be utilized in post-polymerization cross-linking and contribute to polymer network formation. The glass-transition temperature of the homopolymer from AVV (T-g = 77 degrees C) indicates that incorporating its fragments into copolymers might considerably change the intermolecular interactions and physicochemical properties of the resulting materials. Reactivity ratios (r(1), r(2)) obtained in AVV copolymerization with styrene and calculated Q - e parameters of AVV confirm that this monomer copolymerization is described with the classical Mayo-Lewis equation. In this work, latexes from AVV and a renewable acrylic monomer from high oleic soybean oil were synthesized using the miniemulsion process. When the resulting biobased latex films are oxidatively cured, thermomechanical properties of the latex network are determined by the cross-link density, controlled by the ratio of rigid and soft fragments of AVV and the high oleic soybean oil-based monomer, respectively. Depending on the monomer ratio in the feed, polymeric materials with essentially different viscoelastic behaviors were obtained. Being a structural analogue to styrene, 3-allyl-5-vinylveratrole may function as its renewable replacement in free-radical polymerization, particularly in sustainable latexes. Assuming a variety of plant/vegetable oil-based acrylic monomers available, combining such monomers with AVV can become a promising platform for controlling properties of biobased latex polymer networks and their performance.

Automated summary

Renewable 3-allyl-5-vinylveratrole (AVV) is a biobased cross-linkable vinyl monomer that can be synthesized from vanillin and potentially serve as a sustainable alternative to styrene in free-radical polymerization. By copolymerizing AVV with other monomers, materials with different viscoelastic behaviors can be obtained, offering a promising platform for controlling properties of biobased latex polymer networks.