Synthesis and polymerizations of monomers bearing phosphonated groups. I. Applications on acrylates and methacrylates

Abstract

The synthesis of (meth)acrylic monomer bearing phosphonic esters, phosphonic acids, and semisalts is presented. This synthesis was performed in four steps. The first concerns the phosphonylation of allyl bromide by Arbuzov reaction. Second is the monoaddition of 2‐mercapto ethanol onto the allyl double bond, whereas the third consists of the acrylation of the previous phosphonated alcohol. The fourth step involves the dealkylation of the phosphonated ester by the mean of trimethyl halosilane and then the hydrolysis of the obtained silyl ester. Finally, the salification of the diacid is performed in order to stabilize the diacid. In the last part of this work two applications of these monomers in the field of additives for adhesives cured by UV or EB were studied. The results clearly show the superiority of phosphonic acid about the homologous esters. Moreover, the number of acid group and the neighbouring of this acid play an important part in adhesion phenomenon. © 1994 John Wiley & Sons, Inc. Copyright © 1994 John Wiley & Sons, Inc.