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Synthesis of polyurethanes from saccharide-derived diols and diisocyanates and their hydrolyzability

✍ Scribed by Sirinat Wilbullucksanakul; Kazuhiko Hashimoto; Masahio Okada


Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
547 KB
Volume
197
Category
Article
ISSN
1022-1352

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✦ Synopsis


Polyurethanes with saccharide moieties in their repeating units (8 and 9) were prepared by polyaddition of methyl aand ~-~-g~ucofuranosidurono-6,3-lactones (3a and 38, respectively) and 1,43,6-dianhydro-~-glucitol(4) with hexamethylene diisocyanate (5 a) and methyl (S)-2,6-diisocyanatohexanoate (5 b), which was derived from L-lysine, in NN-dimethylformamide at 25 "C using dibutyltin dilaurate as a catalyst. Their properties were compared with those of the polyurethanes (6 and 7) prepared from ~-glucaro-l,4:6,3-dilactone (1) and D-mannaro-l,4:6,3-dilactone (2), respectively, in our previous work. Hydrolyzability of the polyurethanes containing 1, 2, or 3a units in buffer solutions was found to be higher than that of the polyurethanes derived from 3p or 4.

Recently, polyurethanes 6 and 7 were found to be hydrolyzed in phosphate buffers ").

The introduction of dilactone skeletons into the main chains may increase the hydrolyzability of the resulting polyurethanes.

In this work, saccharide-derived polyurethanes having one and no lactone moieties in the repeating units (8 and 9, respectively) were prepared through the polyaddition of methyl aand /3-~-glucofuranosidurono-6,3-lactone (3a and 38, respectively) and 1,43,6-dianhydro-~-glucitol(4) with diisocyanates (5 a and 5 b), and their solubilities, mechanical strength, transition temperatures, and hydrolyzability were determined and compared with those of 6 and 7 having dilactone moieties in the repeating units.


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