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 derivates yield soluble homopolymers with common radical initiators. The m-TMI carbamoyl phosphonates were copolymerized with styrene and with acrylates yielding soluble materials with > 50 mol% incorporation of the phosphonate monomer. The side chain carbamoyl phosphonate group drastically lowers the T sub g relative to those of the parent polymers. Thermogravimetric studies suggest the NHC(O)--P(O)(OR) sub 2 bond to be stable to approx 225 deg C. The radiopacifying salt UO sub 2 (NO sub 3 ) sub 2 6 H sub 2 O yields transparent films with the phosphonate-containing polymers. The T sub g increases with uranyl content.