NOVEL CARBAMOYL PHOSPHONATE MONOMERS AND POLYMERS FROM UNSATURATED ISOCYANATES

Carbamoyl phosphonate derivatives of methacrylic acid and alpha-methyl styrene were synthesized in good yield by reacting dimethyl and diethylphosphite with isocyanato ethylmethacrylate (IEM) or with meta-isopropenyl-alpha,alpha-dimethylbenzylisocyanate (m-TMI). The IEM derivatives yield soluble homopolymers with common radical initiators. The m-TMI carbamoyl phosphonates were copolymerized with styrene and with acrylates yielding soluble materials with better than 50 mol % incorporation of the phosphonate monomer. The side chain carbamoyl phosphonate group drastically lowers the T(g) relative to those of the parent polymers. Thermogravimetric studies suggest the NHC (O) - P (O) (OR)2 bond to be stable to about 225-degrees-C. The radiopacifying salt UO2(NO3)26 H2O yields transparent films with the phosphonate-containing polymers. The T(g) increases with uranyl content.