Synthesis and characterization of monomers and polymers for adhesives from methyl oleate

Abstract The focus of this work is to synthesize a monomer from a fatty acid methyl ester capable of forming high molecular weight polymers. The mono‐unsaturation in the starting material, methyl oleate, was first epoxidized using a peroxy acid. This intermediate material was further modified using acrylic acid. The acrylated molecule is able to participate in free‐radical polymerization reactions to form high molecular weight polymers. The rate of polymerization was low because of the long aliphatic structure of the monomer. It is hypothesized that the polymerization reaction occurred in the interface between the particle and water, thereby slowing down the reaction. After 18 h of reaction, a monomer conversion of approximately 91% was achieved. A maximum weight‐average molecular weight of approximately 10 6 g/mol was observed after 14 h of reaction. At early reaction times linear polymers were formed. However, as the reaction time increased, the amount of branching that occurred on the polymer molecule increased, as indicated by gel permeation chromatography and light scattering. This has been attributed to chain transfer to polymer via hydrogen abstraction from a tertiary backbone C–H bond. The resulting polymer may be of considerable interest for pressure‐sensitive adhesive applications. © 2002 John Wiley & Sons, Inc. J Polym Sci Part A: Polym Chem 40: 451–458, 2002; DOI 10.1002/pola.10130