ADMET polymerization of bio-based biphenyl compoundsElectronic supplementary information (ESI) available: 1H, 13C NMR of the monomers, SEC, DSC and TGA analyses of the polymers. See DOI: 10.1039/c5py01232e

• Main Authors: Llevot, A, Grau, E, Carlotti, S, Grelier, S, Cramail, H
• Format: Journal Article
• Language: English
• Published: 03.11.2015
• ISSN: 1759-9954; 1759-9962
• DOI: 10.1039/c5py01232e

Four biphenyl monomers derived from vanillin or eugenol were synthesized and polymerized by the ADMET methodology. The biphenyl compounds were produced by enzymatic dimerization of 2-methoxy-4-methylphenol, methyl vanillate, vanillin and eugenol. Further chemical modifications of the obtained dimers such as transesterification, Wittig reaction or allylation led to α,ω-dienes. The reactivity of these bio-based monomers towards ADMET polymerization employing several catalysts was investigated. Only oligomers were obtained when the diallylated compound was employed. The polymers based on dieugenol and the bis-unsaturated diester exhibit good thermal stability and T g at 17 and 54 °C, respectively. Polymerization of the divinyl compound obtained by the Wittig reaction of divanillin showed a reasonable molar mass of 30 000 g mol −1 , a high T g at around 160 °C and thermostability with a 5% weight loss occurring at 380 °C. Bio-based phenols were dimerized and employed as monomers in ADMET polymerization.