Abstract
The synthesis and radical polymerization of N-methacryloyl-L-threo-β-hydroxyaspartic acid dimethyl ester (MA-H-M) were carried out. The corresponding polymethacrylamide [poly(MA-H-M) with Mns 38900—484000 was obtained in 28—93% yield. The ester moiety of poly(MA-H-M) could be hydrolyzed with alkaline in quantitative conversion to afford the corresponding polymer [poly(MA-H)], which could be also obtained by the radical polymerization of N-methacryloyl-L-threo-β-hydroxyaspartic acid (MA-H). Poly(MA-H) was quantitatively converted to poly(MA-H-M) by treatment with diazomethane. Poly(MA-H) showed pKa1 and pKa2 (3.74 and 6.37) Iarger than the model compound of the monomer unit of the polymer. N-pivaloyl-L-threo-β-hydroxyaspartic acid (pKa1 2.75, pKa2 4.41). The viscosity of poly(MA-H) increased with pH up to 6—7, the maximum value.
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Sanda, F., Kurokawa, T. & Endo, T. Synthesis, Reactions, and Electrolyte Properties of Polymethacrylamides Having the L-threo-β-Hydroxyaspartic Acid Moiety. Polym J 31, 353–358 (1999). https://doi.org/10.1295/polymj.31.353
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DOI: https://doi.org/10.1295/polymj.31.353