SYNTHESIS AND POLYMERIZATION OF FLUORINAT ED ACRYLIC-MONOMERS SUBSTITUTED IN ALPHA-POSITION .4. APPLICATIONS TO 2-PERFLUOROOCTYLETHYL ALPHA-ACETOXYACRYLATE AND ALPHA-PROPIONYLOXYACRYLATE
B. Guyot et al., SYNTHESIS AND POLYMERIZATION OF FLUORINAT ED ACRYLIC-MONOMERS SUBSTITUTED IN ALPHA-POSITION .4. APPLICATIONS TO 2-PERFLUOROOCTYLETHYL ALPHA-ACETOXYACRYLATE AND ALPHA-PROPIONYLOXYACRYLATE, Macromolecular chemistry and physics, 196(6), 1995, pp. 1875-1886
The synthesis of the two monomers 2-perfluorooctylethyl alpha-acetoxya
crylate (1) and 2-perfluorooctylethyl alpha-propionyloxyacrylate (2) w
as performed in two steps starting from ethyl pyruvate and 2-perfluoro
oclylethanol with overall yields of about 56% and 50%, respectively. T
ransesterification of ethyl pyruvate with the adequate fluorinated alc
ohol followed by enol acylation gave 1 and 2, respectively. The kineti
c 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 prop
agation 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 wer
e compared to those of commercially available fluorinated acrylates an
d methacrylates.