Cyclic poly(l-lactide)s via ring-expansion polymerizations catalysed by 2,2-dibutyl-2-stanna-1,3-dithiolane

Literature Information

Publication Date 2017-01-31
DOI 10.1039/C6PY02166B
Impact Factor 5.582
Authors

H. R. Kricheldorf, S. M. Weidner, F. Scheliga


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Abstract

L-Lactides were polymerized in bulk at 120 or 160 °C with cyclic dibutyltin catalysts derived from 1,2-dimercaptoethane or 2-mercaptoethanol. Only linear chains having one benzyl ester and one OH-end group were obtained when benzyl alcohol was added. When L-lactides were polymerized with neat dibutyl-2-stanna-1,3-dithiolane, exclusively cyclic polylactides were formed even at 120 °C. The temperature, time and monomer/catalyst ratio (M/C) were varied. These results are best explained by a combination of ring-expansion polymerization and ring-extrusion of cyclic oligo- or polylactides with elimination of the cyclic catalyst. Neither syntheses of linear polylactides nor of cyclic lactides involved racemization up to 20 h at 160 °C.

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