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Issue 6, 2010
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High Tg aliphatic polyesters by the polymerization of spirolactide derivatives

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Abstract

A series of bicyclic and tricyclic lactide derivatives was prepared using L-lactide as the starting material. Exomethylene-lactide served as a platform for the Diels–Alder addition of various dienes to afford norbornene-, cyclohexadiene-, and isoprene-lactide derivatives. Norbornene-lactide (NL) was also hydrogenated to the saturated norbornane analog. These new lactide derivatives were subjected to ring-opening polymerization using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as the catalyst. Homopolymers of poly(cyclohexadiene-lactide) (Mn = 6.4 kg mol−1), poly(isoprene-lactide) (Mn = 15.3 kg mol−1), and poly(norbornane-lactide) (Mn = 34.4 kg mol−1) exhibited glass transition temperatures (Tg's) of 119 °C, 77 °C, and 107 °C, respectively. The decomposition temperature (Td) of unsaturated PLA derivatives was ≤280 °C, whereas saturated poly(norbornane-lactide) has a Td of 300 °C. Additionally, a series of poly(norbornene-lactide-s-L-lactide) (P(NL-s-L)) copolymers with varying ratios of NL and L-lactide were prepared. The Tg's of the P(NL-s-L) samples ranged from 61 to 100 °C, and the values were well-described by the Fox equation.

Graphical abstract: High Tg aliphatic polyesters by the polymerization of spirolactide derivatives

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Publication details

The article was received on 26 Jan 2010, accepted on 09 Mar 2010 and first published on 09 Apr 2010


Article type: Paper
DOI: 10.1039/C0PY00029A
Citation: Polym. Chem., 2010,1, 870-877
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    High Tg aliphatic polyesters by the polymerization of spirolactide derivatives

    G. L. Fiore, F. Jing, V. G. Young, Jr., C. J. Cramer and M. A. Hillmyer, Polym. Chem., 2010, 1, 870
    DOI: 10.1039/C0PY00029A

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