Novel carbamoyl phosphonate monomers and polymers from unsaturated isocyanates

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Abstract
Carbamoyl phosphonate derivatives of methacrylic acid and α‐methyl styrene were synthesized in good yield by reacting dimethyl and diethylphosphite with isocyanato ethylmethacrylate (IEM) or with meta‐isopropenyl‐α,α‐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 Tg relative to those of the parent polymers. Thermogravimetric studies suggest the NHC(O)P(O)(OR)2 bond to be stable to about 225°C. The radiopacifying salt UO2(NO3)26 H2O yields transparent films with the phosphonate‐containing polymers. The Tg increases with uranyl content. © 1993 John Wiley & Sons, Inc.

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