TY - JOUR
T1 - Dual-functional, aromatic, epoxy-methacrylate monomers from bio-based feedstocks and their respective epoxy-functional thermoplastics
AU - Bassett, Alexander W.
AU - Sweet, Kayla R.
AU - O'Dea, Robert M.
AU - Honnig, Amy E.
AU - Breyta, Claire M.
AU - Reilly, Julia H.
AU - La Scala, John J.
AU - Epps, Thomas H.
AU - Stanzione, Joseph F.
N1 - Funding Information:
A.W.B., K.R.S., A.E.H., C.M.B., J.H.R., and J.F.S. acknowledge financial support of the United States Army Research Laboratory through Cooperative Agreements W911NF‐14‐2‐0086 and W911NF‐16‐2‐0225 for the development of the dual‐functional monomers and preparation of their respective thermoplatics. R.M.O., J.F.S., and T.H.E. acknowledge financial support from NSF grant CHE‐1507010 for the surface characterization of the prepared thermoplastics. The authors would also like to thank Professor Jonathan Foglein of the Chemistry Department at Rowan University for assistance with the NMR spectrometer and Waters Corporation for their assistance with running HRMS.
Publisher Copyright:
© 2020 Wiley Periodicals, Inc.
Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.
PY - 2020/3/1
Y1 - 2020/3/1
N2 - Dual-functional monomers consist of two distinctly different functional groups that enable chemical versatility. The most readily available epoxy-methacrylate dual-functional monomer is glycidyl methacrylate (GMA). In an effort to produce bio-based, aromatic complements to GMA, asymmetric phenolic diols (vanillyl alcohol, syringyl alcohol, gastrodigenin, and tyrosol) were identified and selectively epoxidized at the aromatic hydroxyl followed by subsequent esterification at the aliphatic hydroxyl to prepare dual functional monomers, vanillyl alcohol epoxy-methacrylate (VAEM), syringyl alcohol epoxy-methacrylate (SAEM), gastrodigenin epoxy-methacrylate (GDEM), and tyrosol epoxy-methacrylate (TEM). These monomers are viable platforms for a multitude of applications due to their unique chemical functionalities. VAEM, SAEM, GDEM, and TEM were homopolymerized individually to produce aromatic, bio-based epoxy-functional thermoplastics analogous to poly(GMA). 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 (initial decomposition temperatures >260 °C in air) relative to poly(GMA), while retaining similar glass transition temperatures (~ 65 °C) and surface energies (~ 53 mJ m−2); thus, these materials could be substituted for poly(GMA) and enable use in higher-temperature applications.
AB - Dual-functional monomers consist of two distinctly different functional groups that enable chemical versatility. The most readily available epoxy-methacrylate dual-functional monomer is glycidyl methacrylate (GMA). In an effort to produce bio-based, aromatic complements to GMA, asymmetric phenolic diols (vanillyl alcohol, syringyl alcohol, gastrodigenin, and tyrosol) were identified and selectively epoxidized at the aromatic hydroxyl followed by subsequent esterification at the aliphatic hydroxyl to prepare dual functional monomers, vanillyl alcohol epoxy-methacrylate (VAEM), syringyl alcohol epoxy-methacrylate (SAEM), gastrodigenin epoxy-methacrylate (GDEM), and tyrosol epoxy-methacrylate (TEM). These monomers are viable platforms for a multitude of applications due to their unique chemical functionalities. VAEM, SAEM, GDEM, and TEM were homopolymerized individually to produce aromatic, bio-based epoxy-functional thermoplastics analogous to poly(GMA). 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 (initial decomposition temperatures >260 °C in air) relative to poly(GMA), while retaining similar glass transition temperatures (~ 65 °C) and surface energies (~ 53 mJ m−2); thus, these materials could be substituted for poly(GMA) and enable use in higher-temperature applications.
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U2 - 10.1002/pol.20190110
DO - 10.1002/pol.20190110
M3 - Article
AN - SCOPUS:85092436197
VL - 58
SP - 673
EP - 682
JO - Journal of Polymer Science
JF - Journal of Polymer Science
SN - 2642-4150
IS - 5
ER -