2,5–furandicarboxylic Acid Dicinamil Ether and New Copolymers on Its Basis

Abstract

A method for the synthesis of dicinamyl ester of 2,5-furandicarboxylic acid (DCF) a new unsaturated compound of the furan series and potential monomer for producing copolymers with various vinyl compounds and based on them a new generation of construction and ion-exchange materials has been developed. DCF does not form homopolymers as in bulk as in solution (toluene solvent). However, DCF is actively copolymerized with styrene, methyl methacrylate, methacrylic and acrylic acids to form cross-linked polymers with varying degrees of crosslinking. The copolymerization constants of DCF with all investigated vinyl compounds were determined. The DCF copolymers are enriched with comonomer units for all ratios of the components in the initial reaction mixture. They are statistical, and the comonomer units in the macromolecule are randomly arranged. Copolymers with styrene or methyl methacrylate have higher mechanical strength compared to polystyrene and polymethyl methacrylate. Copolymers containing carboxyl groups and 10-20 % wt. crosslinking agent exhibit good ion-exchange properties with respect to heavy metals. The equilibrium adsorption amount of Cu2+ onto ion-exchange сopolymers (221-234 mg/g) was almost twice as large as that onto Amberlite IRC-748 (120.0 mg/g). Materials with a crosslinking agent content of 2.5-5% wt. form polymer gels with high water absorption. Materials containing 2.5 % wt. crosslinking agent (≥ 1400 % for copolymer DCF /acrylic acid and ≥ 1700 for copolymer DCF/methacrylic acid) are showed maximum swelling. These materials can be recommended as water absorbers.