Synthesis of novel carvone (meth)acrylate monomers for the production of hydrophilic polymers with high terpene content

The terpene-based monomers and polymers reported in the literature are mostly hydrophobic and this is limiting their use in aqueous environments. To address this drawback, we have developed a novel synthetic strategy to functionalise a model terpene monomer in order to improve hydrophilicity and the number of polar groups on the polymer side chains. To produce a highly hydrophilic monomer, carvone (meth)acrylate was chosen as the primary feedstock. Carvone has more functionalisable double bonds than other commercial cyclic terpenes and offers the potential for the maximum number of hydrophilic groups per monomer molecule. The monomers were homopolymerised and copolymerised to generate novel green hydrophilic and amphiphilic terpene-based polymers which were characterised by 1H–13C NMR, gel permeation chromatography, TGA and DSC analyses. © 2020 Society of Industrial Chemistry.