Synthesis and characterization of a soybean oil‐based macromonomer

Abstract

An acrylate‐functional soybean oil‐based macromonomer (SoyAA‐1) was synthesized in high yields utilizing sequential amidation and acrylation processes to serve as an internal plasticizer in emulsion polymers. The structure and structure–property relationships of this unique macromonomer were validated with FTIR, NMR, and LC‐MS. The viability of SoyAA‐1 as a comonomer in emulsion polymerization was established via copolymerization with methyl methacrylate (MMA) at varying copolymer weight compositions. The effect of increasing SoyAA‐1 levels and concomitantly higher allylic functionality was measured through film coalescence, minimum film forming temperature, and initial and progressively increasing glass transition temperature(s). The results indicate that synthetic modification of a renewable resource, soybean oil, can yield a valuable monomer that can be copolymerized in high yields via emulsion polymerization to produce practical and mechanically stable latexes for a variety of coatings applications. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 40249.

Sustainable thermoplastic elastomers derived from plant oil and their “click-coupling” via TAD chemistry

“…50 As demonstrated by Rawlins and his coworkers, acrylate soybean oil polymer (PSBA) exhibits a low T g of −32 °C. 51 Accordingly, we hypothesized that renewable acrylate soybean oil monomers could be used to replace isoprene/butadiene as the soft segment in the design of TPEs.…”

Fatty Acid-Based Radically Polymerizable Monomers: From Novel Poly(meth)acrylates to Cutting-Edge Properties

“…76 Similar work of amidation and acrylation processes have been reported by Delatte et al in which soybean oil was functionalized with polymerizable moities via two synthetic routes after amidation: acryloyl chloride in the presence of trimethylamine and direct esterification with acrylic acid. 77 The resulting soyamide acrylate monomers were obtained in high yields in both cases (99-100 %). This strategic pathway can be used for any plant oil but also directly with FA or derivatives to afford suitable monomers leading to linear polymers through radical polymerization.…”

“…In a further work, the same procedure with different amino alcohols has been used to afford other monomers for further radical polymerization . In a similar work, soybean oil was functionalized with polymerizable moieties via two synthetic routes after amidation: trans­esterification with acryloyl chloride in the presence of trimethylamine and direct esterification with acrylic acid . The resulting soy­amide acrylate monomers were obtained in high yields in both cases (99–100%).…”

Straightforward Synthesis of Amido Polyols from Epoxidized Soybean Oil for Polyurethane Films

“…One of the most important reactions involving VOs is the preparation of N ‐hydroxyalkylamides, usually obtained by the amidation of the triglyceride structure with aminoalcohols, in the presence of sodium methoxide, [ 6,9–13 ] potassium hydroxide, [ 14,15 ] or NaOH/CaO in nanocrystalline form [ 16 ] as catalysts. The obtained N ‐hydroxyalkylamides are typically converted into acrylates or methacrylates [ 6,9,10,17 ] and used, e.g., in emulsion polymerization, [ 9 ] as precursors for the preparation of deformable bioelastomers [ 11 ] or as precursors for biobased thermosets. [ 12–14 ] The same type of reactions can be employed with epoxidized VOs, with the advantage that the oxirane ring can also undergo modifications through the nucleophilic reaction with hydroxyl or amine‐containing reagents.…”