Dual-functional monomers consist of two distinct functional groups that enable chemical versatility. Glycidyl methacrylate (GMA) is the sole commercially available epoxy-methacrylate monomer. GMA can be polymerized to form poly(GMA), an epoxy-functional thermoplastic with highly versatile and tunable chemical, mechanical, and thermal properties. In an effort to produce bio-based, aromatic complements to GMA, the asymmetric phenolic diols vanillyl alcohol (VA), syringyl alcohol (SA), gastrodigenin (GD), and tyrosol were identified. VA, SA, and GD are derived from lignin, whereas tyrosol can be extracted from olive mill wastewater. Each diol was selectively epoxidized at the aromatic hydroxyl group followed by esterification at the aliphatic hydroxyl group to prepare dual functional monomers vanillyl alcohol epoxy-methacrylate (VAEM), syringyl alcohol epoxy-methacrylate (SAEM), gastrodigenin epoxy-methacrylate (GDEM), and tyrosol epoxy-methacrylate (TEM). VAEM, SAEM, GDEM, and TEM were polymerized to form bio-based epoxy-functional poly(GMA) alternatives. The molecular weight distributions and thermal properties of each polymer were evaluated, as were the surface characteristics of flow-coated thin films from these polymers. Most of the newly prepared epoxy-functional thermoplastics exhibited increased thermal stability relative to poly(GMA) while retaining similar glass transition temperatures and surface energies; thus, these materials could be substituted for poly(GMA) and be useful in higher-temperature applications.

Dual-functional epoxy-methacrylate monomers from bio-based feedstocks and their respective epoxy-functional thermoplastics

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.