Synthesis and characterization of glucose derivatives copolymers

CARLOS ALEJANDRO RODRÍGUEZ RAMIREZ; VERÓNICA MANZANO; NANCY L. GARCÍA; NORMA D´ACCORSO

Florianopolis

Simposio; XXXth International Carbohydrate Symposium; 2022

Biobased polymers have positioned as "sustainable" materials for the development of the world economy. The demand for new materials based on carbohydrates is on constantly rise and study, since these materials have significant advantages such as high availability, low cost, and biodegradability. The aim of this project is the synthesis of new copolymers incorporating carbohydrates and other biomass components such as cinnamic alcohol. Initially, the polymerization was standardized using a benzyl alcohol derivative as a model compound and then extrapolated to cinnamic alcohol. The synthesis of the glucose derivative 1 involved the formation of de 1,2,5,6-di-O-isopropylidene-α-D-glucofuranose derivative by a treatment with acetone in an acid medium, followed by esterification with methacrylic acid using DCC. An analogous esterification procedure was used for the synthesis of compound 3 and 4, derived from benzyl and cinnamic alcohol, respectively.Homopolymerization of 1 to gain 2 required the use AIBN as initiator. Monomers 1 and 3 were copolymerized in different proportions, yielded copolymers 5-7. A similar procedure using 1 with 4 afforded 8-10 products. Molecular weights for the polymers were determined by GPC producing polymers with Mn~2500 approximately. All products were fully characterized physical and thermally (contact angle, TGA, DSC), spectroscopical techniques (FTIR, mono- and bi-dimensional NMR) as well as by X-ray diffraction (XRD) and SEM microscopy.