Renewable thermosetting resins and thermoplastics from vanillin. Issue 2 (4th December 2014)

• Record Type: Journal Article
• Authors: Harvey, Benjamin G.; Guenthner, Andrew J.; Meylemans, Heather A.; Haines, Shannon R. L.; Lamison, Kevin R.; Groshens, Thomas J.; Cambrea, Lee R.; Davis, Matthew C.; Lai, William W.
• Is Part Of: Green chemistry. Volume 17:Issue 2(2015)
• Page Start: 1249
• Page End: 1258
• Publication Date: 2014-12-04
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/c4gc01825g
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : New high temperature thermosetting resins and a thermoplastic polycarbonate have been synthesized from the renewable phenol vanillin. Abstract : Two cyanate ester resins and a polycarbonate thermoplastic have been synthesized from vanillin. The bisphenol precursors were prepared by both an electrochemical route as well as by a McMurry coupling reaction. 1, 2-Bis(4-cyanato-3-methoxyphenyl)ethene (6 ) had a high melting point of 237 °C and did not cure completely under a standard cure protocol. In contrast, the reduced version, 1, 2-bis(4-cyanato-3-methoxyphenyl)ethane (7 ) melted at 190 °C and underwent complete cure to form a thermoset material with T g = 202 °C.7 showed thermal stability up to 335 °C and decomposed via formation of phenolics and isocyanic acid. A polycarbonate was then synthesized from the reduced bisphenol by a transesterification reaction with diphenylcarbonate. The polymer had M n = 3588, M w / M n = 1.9, and a T g of 86 °C. TGA/FTIR data suggested that the polycarbonate decomposed via formation of benzodioxolones with concomitant elimination of methane. The results show that vanillin is a useful precursor to both thermosetting resins and thermoplastics without significant modification.