SYNTHESIS AND POLYMERIZATION OF FLUORINATED ACRYLIC-MONOMERS SUBSTITUTED IN ALPHA-POSITION .4. APPLICATIONS TO 2-PERFLUOROOCTYLETHYL ALPHA-ACETOXYACRYLATE AND ALPHA-PROPIONYLOXYACRYLATE

The synthesis of the two monomers 2-perfluorooctylethyl alpha-acetoxyacrylate (1) and 2-perfluorooctylethyl alpha-propionyloxyacrylate (2) was performed in two steps starting from ethyl pyruvate and 2-perfluorooclylethanol with overall yields of about 56% and 50%, respectively. Transesterification of ethyl pyruvate with the adequate fluorinated alcohol followed by enol acylation gave 1 and 2, respectively. The kinetic study of polymerization of monomers 1 and 2 led to the determination of the values of the ratio of the square of the rate constant of propagation over the rate constant of termination k(p)(2)/k(te) equal to 9,2 . 10(-3) and 9,1 . 10(-3) L . mol(-1). s(-1), respectively, and were compared to those of commercially available fluorinated acrylates and methacrylates.