Exchange reactions of poly‐2‐(N‐phthalimido)ethyl acrylate with hydroxy and amino compounds

To determine the optimal general condition for the synthesis and polymerisation of 2‐(N‐phthalimido)ethyl acrylate (NPEA), as well as the exchange reactions of poly‐NPEA with aminated and hydroxylated compounds as a model compound.

Preparation of 2‐(N‐phthalimido)ethyl acrylate by the reaction of N‐(2‐hydroxyethyl) phthalimide with acrylic acid and polymerisation of the resulting monomer. The exchange reactions of the resulting polymer with amines and hydroxy compounds were carried out. The structure of the resulting compounds were characterised.

NPEA was prepared by the reaction of N‐(hydroxyethyl)phthalimide with acrylic acid. The monomer prepared was easily polymerised. The reactions of the resulting polymer with amines and hydroxy compounds were studied. In all cases, the exchange reactions were almost practically quantitative, which was confirmed by elemental analysis, IR and ¹HNMR spectroscopy. Also, it was clear that poly‐NPEA showed a good behaviour as a model compound for a long active polymeric‐drug.

The new monomer described in the present investigation may be useful for the preparation of polymeric‐drug adducts. Also, similar monomeric phthalimides may be synthesised starting from a number of other hydroxy or amino acids, thus providing wider possibilities for the synthesis of pharmacologically active polymers.

The method for preparation of monomer is simple and the exchange reactions provide a simple and practical solution to prepare some classes of macromolecular drugs.

The method of preparation of polymers was novel and may be useful for preparation of polymeric‐drug adducts.