Polymer Bulletin

, Volume 9, Issue 6–7, pp 276–283 | Cite as

New polymer syntheses

8. Synthesis and polymerization of L-lactic acid O-carboxyanhydride (5-methyl-dioxolan-2,4-dione)
  • Hans R. Kricheldorf
  • J. Michael Jonté


L-Lactic acid O-carboxyanhydride (L-Lac-OCA) was prepared by phosgenation of L-lactic acid lithium salt. Its polymerization was conducted using a variety of initiators, and the resulting poly(L-lactides) were characterized by 1H-and 13C-NMR spectra, by vapor pressure osmometry (VPO) and by optical rotation. Number average molecular weights > 3 000 were never obtained. Also polymerizations of D,L-Lac-OCA did not give higher Mn's. The formation of isotactic triads was favored under all conditions. Furthermore, copolymerizations of L-Lac-OCA and various α-amino acid N-carboxyanhydrides (NCAs) only yielded low molecular weight poly(depsipeptides). The polymerization mechanism is discussed.


Lithium Vapor Pressure Triad Copolymerization Average Molecular Weight 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1).
    J.Smith and J.Tighe; Makromol.Chem. 182, 313 (1981)Google Scholar
  2. 2).
    M.Goodman and U.Arnon; Biopolymers 1, 500 (1963)Google Scholar
  3. 3).
    H.R.Kricheldorf and M.Fehrle; Chem.Ber. 107, 3533 (1974)Google Scholar
  4. 4).
    H.R.Kricheldorf and K.Bösinger; Makromol.Chem. 177, 1243 (1976)Google Scholar
  5. 5).
    R.Idelson and E.R.Blout; J.Ann.Chem.Soc. 79,39,48 (1957)Google Scholar
  6. 6).
    C.Naegeli; Helv.Chim.Acta 18, 142 (1935)Google Scholar
  7. 7).
    St.Goldschmidt and M.Wick; Liebigs Ann.Chem.575,217 (1952)Google Scholar
  8. 8).
    H.R.Kricheldorf and E.Leppert; Makromol.Chem.167,47 (1973)Google Scholar
  9. 9).
    W.H.Davies; J.Chem.Soc. (London) 1357 (1951)Google Scholar
  10. 10).
    E.Lillie and R.C.Schulz; Makromol.Chem.176, 1901 (1975)Google Scholar
  11. 11).
    H.R.Kricheldorf and T.Mang; Makromol.Chem.182, 3077 (1981)Google Scholar
  12. 12).
    H.R.Kricheldorf and T.Mang; Makromol.Chem.183, 2113 (1982)Google Scholar
  13. 13).
    H.R.Kricheldorf and W.E.Hull; Biopolymers 21, 1635 (1982)Google Scholar
  14. 14).
    A.Schindler and D.Harper; J.Polym.Sci.Polym.Letters Ed.14 729 (1976)Google Scholar
  15. 15).
    F.Chabot and M.Vert; Polymers (1983) in pressGoogle Scholar

Copyright information

© Springer-Verlag 1983

Authors and Affiliations

  • Hans R. Kricheldorf
    • 1
  • J. Michael Jonté
    • 1
  1. 1.Institut für Angewandte Chemie der UniversitätHamburg 13Germany

Personalised recommendations