Ring‐opening polyaddition of a saccharic acid dilactone prepared from D‐glucose, D‐glucaro‐1,4 : 6,3‐dilactone, with several alkylenediamines proceeded at room temperature with no catalyst. The resulting new polyamides carrying many pendant hydroxyl groups, poly(alkylene D‐glucaramide)s, were more amorphous and hydrophilic than the corresponding nylons having no hydroxyl groups, and were hydrolyzed more easily than the latter in an acidic condition. The ring‐opening ability of D‐mannaro‐1,4:6,3‐dilactone, which was another saccharic acid dilactone obtained from D‐mannitol, was found to be lower than that of the D‐glucaric analogue. © 1993 John Wiley & Sons, Inc.

New hydrolyzable gels bearing saccharide, L-lysine, and poly(oxyethy1ene) moieties were prepared via polyaddition of methyl ~-~-glucofuranosidurono-6,3-lactone (1) and poly(ethy1ene glycol) (PEG, M, = 1000) with an L-lysine derivative, methyl (S)-2,6-diisocyanatohexanoate (2), using dibutyltin dilaurate and triisocyanate 3 as a catalyst and a crosslinking agent, respectively. The swelling ratio and rate of hydrolysis of these gels in phosphate buffers increased with the content of PEG. Hydrolysis of these gels was enhanced by increasing the pH of phosphate buffer solution in the range from 5.5 to 8.0, while the gel having only repeating units derived from 1 and 2 but no PEG was hardly hydrolyzed in any buffer solutions (pH 5.5, 7.0, 8.0). The release of hydrophilic 5(6)-carboxyfluorescein (CF) from these gels in buffer solution of pH 8.0 was faster than that of hydrophobic magnesium 8-anilino-1-naphthalenesulfonate (ANS). The release of ANS from the gel was enhanced with the swelling caused by hydrolysis.

Four different poly(ether urethane) gels were prepared by polyaddition of saccharide derivatives (1, 2, 3a, or 38) and poly(propy1ene glycol) with an L-lysine-derived diisocyanate, methyl (S)-2,6-diisocyanatohexanoate (4). Dibutyltin dilaurate and triisocyanate 5, that was also derived from L-lysine, were used as a catalyst and a crosslinking agent, respectively. Hydrogels containing 1, 2 or 3a were hydrolyzed in phosphate buffers (pH 5.5, 7.0, 8.0) at 27 "C, while the hydrolysis of the gel bearing 38 did not occur even after immersion for 3 months. Release of 5(6)-carboxyfluorescein (CF) and magnesium 8-anilino-1-naphthalenesulfonate (ANS) from the hydrogels was investigated in buffers of different pH. The release behavior was significantly controlled by the degree of hydrolysis of the gels. Both hydrolysis and the release behavior of these gels depended on the pH value.

No abstract