Recently, we reported on synthesis and characterization of new biobased acrylic monomers derived from variety of plant/vegetable oils (soybean, olive, linseed, sunflower, corn, canola etc.) and their application in free radical polymerization. Copolymerization study on plant oil-based monomers (POBMs) with a variety of petroleum-based commodity comonomers demonstrated that incorporation of POBM into macromolecular structure provides internal plasticization, hydrophobization, improves toughness of crosslinked latex polymers and promotes biodegradability of resulted biobased latexes. However, excessive polymers softening was observed when POBM content in the resulted copolymers exceeds 60 wt.%, making latexes “too soft” and not applicable for film preparation. To be able to increase biobased content without worsening the material properties, alternative biobased counterparts may be considered for copolymerization with POBM. For this, new vanillin-derived 3-allyl-5-vinylveratrole (AVV) was chosen. Having chemical structure similar to petroleum-based Styrene, the AVV can perform as its biobased alternative when incorporated in macromolecular structure. Incorporation of AVV fragments into latex copolymers could balance mechanical properties of the resulted macromolecules by enhancing the materials strength and toughness. In addition, presence of allyl bond in the AVV chemical structure may contribute to its reactivity in free radical reactions, if allyl groups are retained during the polymerization-they can be used for post-polymerization cross-linking. The obtained results show that AVV successfully undergoes free radical homopolymerization and chain copolymerization with POBM (monomer from high oleic soybean oil was used). As determined by <sup>1</sup>H NMR spectroscopy, AVV’s allylic groups remain unreacted under polymerization reaction conditions used in this study. Feasibility of AVV and POBM combination in chain copolymerization was demonstrated. Varying monomers feed ratio, latexes in a broad range of thermo-mechanical properties were synthesized, along with ability to tune tensile properties by crosslinking using allylic groups of AVV fragments.

Vanillin and soy derived vinyl monomers copolymerization targeting synthesis of latexes with high bio-based content

ACS Spring Meeting 2021

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