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SnOct2-Catalyzed Syntheses of Cyclic Poly(l-lactide)s with Catechol as Low-Toxic Co-catalyst

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Abstract

Polymerizations of l-lactide in bulk at 160 or 180 °C were performed with 1/1 mixtures of catechol (CA) or 4-tert-butylcatechol (BuCA) and tin(II)-2-ethylhexanoate (SnOct2) as catalysts and a variation of the Lac/Cat ratio. Weight average molar masses (Mw) up to 170,000 g mol−1 were obtained with CA and up to 120,000 g mol−1 with BuCA. The cyclic structure of the resulting poly(l-lactide)s was proven by MALDI-TOF mass spectrometry and by comparison of their hydrodynamic volumes with those of commercial linear poly(l-lactide)s. The predominance of even-numbered cycles increased with lower temperatures and shorter polymerization times. This finding indicates that the cyclic architecture is the results of a ring-expansion polymerization mechanism. Addition of silylated BuCA as co-catalyst was less favorable than addition of free BuCA.

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Acknowledgements

We wish to thank Profs G. Luinstra and H.-U. Moritz (TMC, Hamburg) and BAM (Berlin) for technical support. Furthermore, we thank Mrs. Rosemarie Laging (BAM, Berlin) for the SEC measurements.

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Authors and Affiliations

  1. Universität Hamburg, Institut für Technische Und Makromolekulare Chemie, Bundesstrasse 45, Hamburg, Germany

    Hans R. Kricheldorf

  2. BAM, Federal Institute for Materials Research and Testing , Richard-Willstätter-Strasse 11, 12489, Berlin, Germany

    Steffen M. Weidner

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  1. Hans R. Kricheldorf
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  2. Steffen M. Weidner
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Correspondence to Hans R. Kricheldorf.

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Kricheldorf, H.R., Weidner, S.M. SnOct2-Catalyzed Syntheses of Cyclic Poly(l-lactide)s with Catechol as Low-Toxic Co-catalyst. J Polym Environ 27, 2697–2706 (2019). https://doi.org/10.1007/s10924-019-01545-5

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