Stereoselective polymerization of lactide

Stereoselective Polymerization with Single-Site Catalysts

Volumn , Issue , 2007, Pages 645-660

  Chisholm, Malcolm H ^a   Zhou, Zhiping ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79955629395     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (65)

1. Kricheldorf, H. R. Syntheses and application of polylactides. Chemosphere 2001, 43, 49-54.
2. Kharas, G. B.; Sanchez-Riera, F.; Severson, D. K. Polymers of lactic acid. Plast. Microbes 1994, 93-137.
3. Gruber, P.; O’Brien, M. Polylactides. Natureworks PLA. Biopolymers 2002, 4, 235-250.
4. Lunt, J.; Bone, J. Properties and dyeability of fibers and fabrics produced from polylactide (PLA) polymers. AATCC Review 2001, 1, 20-23.
5. Dartee, M.; Lunt, J.; Shafer, A. Natureworks PLA: Sustainable performance fiber. Chem. Fibers Int.2000, 50, 546-551.
6. Drumright, R. E.; Gruber, P. R.; Henton, D. E. Polylactic acid technology. Adv. Mater. 2000, 12, 1841-1846.
7. O’Keefe, B. J.; Hillmyer, M. A.; Tolman, W. B. Polymerization of lactide and related cyclic esters by discrete metal complexes. J. Chem. Soc., Dalton Trans. 2001, 2215-2224.
8. Chisholm, M. H.; Zhou, Z. New generation polymers: The role of metal alkoxides as catalysts in the production of polyoxygenates. J. Mater. Chem. 2004, 14, 3081-3092.
9. Nakano, K.; Kosaka, N.; Hiyama, T.; Nozaki, K. Metal-catalyzed synthesis of stereoregular polyketones, polyesters, and polycarbonates. J. Chem. Soc., Dalton Trans. 2003, 4039-4050.
10. Dechy-Cabaret, O.; Martin-Vaca, B.; Bourissou, D. Controlled ring-opening polymerization of lactide and glycolide. Chem. Rev. 2004, 104, 6147-6176.
11. Penczek, S.; Duda, A.; Kowalski, A.; Libiszowski, J.; Majerska, K.; Biela, T. On the mechanism of polymerization of cyclic esters induced by tin(II) octoate. Macromol. Symp. 2000, 157, 61-70.
12. Schwach, G.; Coudane, J.; Engel, R.; Vert, M. Zn lactate as initiator of dl-lactide ring opening polymerization and comparison with Sn octoate. Polym. Bull. 1996, 37, 771-776.
13. Bero, M.; Kasperczyk, J.; Adamus, G. Coordination polymerization of lactides. 3. Copolymerization of l, l-lactide and ε-caprolactone in the presence of initiators containing zinc and aluminum. Makromol. Chem. 1993, 194, 907-912.
14. 13C NMR spectroscopy. Polymer 1996, 37, 201-203.
15. Schwach, G.; Coudane, J.; Engel, R.; Vert, M. Ring opening polymerization of dl-lactide in the presence of zinc metal and zinc lactate. Polym. Int. 1998, 46, 177-182.
16. Kricheldorf, H. R.; Damrau, D. O. Polylactones. Part 37. Polymerizations of l-lactide initiated with Zn(II) l-lactate and other resorbable Zn salts. Macromol. Chem. Phys. 1997, 198, 1753-1766.
17. 2, OR). New J. Chem. 2003, 27, 1167-1176.
18. Nederberg, F.; Connor, E. F.; Glausser, T.; Hedrick, J. L. Organocatalytic chain scission of poly(lactides): A general route to controlled molecular weight, functionality and macromolecular architecture. Chem. Commun. 2001, 2066-2067.
19. Nederberg, F.; Connor, E. F.; Moeller, M.; Glauser, T.; Hedrick, J. L. New paradigms for organic catalysts: The first organocatalytic living polymerization. Angew. Chem., Int. Ed. Engl. 2001, 40, 2712-2715.
20. Connor, E. F.; Nyce, G. W.; Myers, M.; Moeck, A.; Hedrick, J. L. First example of N-heterocyclic carbenes as catalysts for living polymerization: Organocatalytic ring-opening polymerization of cyclic esters. J. Am. Chem. Soc. 2002, 124, 914-915.
21. Myers, M.; Connor, E. F.; Glauser, T.; Mock, A.; Nyce, G.; Hedrick, J. L. Phosphines: Nucleophilic organic catalysts for the controlled ring-opening polymerization of lactides. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 844-851.
22. Nyce, G. W.; Connor, E. F.; Hedrick, J. L. In-situ formation of N-heterocyclic carbenes as organic catalysts for living polymerization. Polym. Mater. Sci. Eng. 2002, 87, 213-214.
23. Nyce, G.W.; Glauser, T.; Connor, E. F.; Moeck, A.;Waymouth, R. M.; Hedrick, J. L. In situ generation of carbenes: A general and versatile platform for organocatalytic living polymerization. J. Am. Chem. Soc. 2003, 125, 3046-3056.
24. Duda, A.; Penczek, S. Thermodynamics of l-lactide polymerization. Equilibrium monomer concentration. Macromolecules 1990, 23, 1636-1639.
25. i): The notable influence of initiator group. New J. Chem. 2003, 27, 1177-1183.
26. Kricheldorf, H. R.; Boettcher, C.; Toennes, K. U. Polylactones. 23. Polymerization of racemic and meso d, l-lactide with various organotin catalysts - stereochemical aspects. Polymer 1992, 33, 2817-2824.
27. Kricheldorf, H. R.; Kreiser-Saunders, I. Polylactides-synthesis, characterization and medical application. Macromol. Symp. 1996, 103, 85-102.
28. Chisholm, M. H.; Iyer, S. S.; Matison, M. E.; McCollum, D. G.; Pagel, M. Concerning the stereochemistry of poly(lactide), PLA. Previous assignments are shown to be incorrect and a new assignment is proposed. Chem. Commun. 1997, 1999-2000.
29. Chisholm, M. H.; Iyer, S. S.; McCollum, D. G.; Pagel, M.; Werner-Zwanziger, U. Microstructure of polylactide. Phase-sensitive HETCOR spectra of poly-meso-lactide, poly-rac-lactide, and atactic polylactide. Macromolecules 1999, 32, 963-973.
30. 1H NMR stereosequence assignments of polylactide using high-resolution solution NMR spectroscopy. Macromolecules 2002, 35, 7700-7707.
31. Kasperczyk, J. E. Microstructure analysis of poly(lactic acid) obtained by lithium tert-butoxide as initiator. Macromolecules 1995, 28, 3937-3939.
32. Kasperczyk, J. E. HETCOR NMR study of poly(rac-lactide) and poly(meso-lactide). Polymer 1999, 40, 5455-5458.
33. Coudane, J.; Ustariz-Peyret, C.; Schwach, G.; Vert, M. More about the stereodependence of dd and ll pair linkages during the ring-opening polymerization of racemic lactide. J. Polym. Sci., Part A: Polym. Chem. 1997, 35, 1651-1658.
34. Chamberlain, B. M.; Cheng, M.; Moore, D. R.; Ovitt, T. M.; Lobkovsky, E. B.; Coates, G. W. Polymerization of lactide with zinc and magnesium β-diiminate complexes: Stereocontrol and mechanism. J. Am. Chem. Soc. 2001, 123, 3229-3238.
35. Bovey, F. A.; Mirau, P. A. Physical properties of synthetic high polymers. In NMR of Polymers; Academic Press: San Diego, CA, 1996; p 459.
36. Spinu, M.; Jackson, C.; Keating, M. Y.; Gardner, K. H. Material design in poly(lactic acid) systems: Block copolymers, star homo- and copolymers, and stereocomplexes. J. Macromol. Sci., Pure Appl. Chem. 1996, A33, 1497-1530.
37. Yui, N.; Dijkstra, P. J.; Feijen, J. Stereo block copolymers of l- and d-lactides. Makromol. Chem.1990, 191, 481-488.
38. Tsuji, H.; Ikada, Y. Stereocomplex formation between enantiomeric poly(lactic acid)s. XI. Mechanical properties and morphology of solution-cast films. Polymer 1999, 40, 6699-6708.
39. Zhong, Z.; Dijkstra, P. J.; Feijen, J. Controlled and stereoselective polymerization of lactide: Kinetics, selectivity, and microstructures. J. Am. Chem. Soc. 2003, 125, 11291-11298.
40. Spassky, N.; Wisniewski, M.; Pluta, C.; Le Borgne, A. Highly stereoelective polymerization of rac-(d, l)-lactide with a chiral Schiff’s base/aluminum alkoxide initiator. Macromol. Chem. Phys. 1996, 197, 2627-2637.
41. Zhong, Z.; Dijkstra, P. J.; Feijen, J. [(salen)Al]-Mediated, controlled and stereoselective ring-opening polymerization of lactide in solution and without solvent: Synthesis of highly isotactic polylactide stereocopolymers from racemic d, l-lactide. Angew. Chem., Int. Ed. Engl. 2002, 41, 4510-4513.
42. 3and S-CHMeCl). Chem. Commun.2005, 127-129.
43. Radano, C. P.; Baker, G. L.; Smith, M. R. III. Stereoselective polymerization of a racemic monomer with a racemic catalyst. Direct preparation of the poly(lactic acid) stereocomplex from racemic lactide. J. Am. Chem. Soc. 2000, 122, 1552-1553.
44. Ovitt, T. M.; Coates, G. W. Stereoselective ring-opening polymerization of rac-lactide with a singlesite, racemic aluminum alkoxide catalyst: Synthesis of stereoblock poly(lactic acid). J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 4686-4692.
45. Ovitt, T. M.; Coates, G.W. Stereoselective ring-opening polymerization of meso-lactide: Synthesis of syndiotactic poly(lactic acid). J. Am. Chem. Soc. 1999, 121, 4072-4073.
46. Ovitt, T. M.; Coates, G. W. Stereochemistry of lactide polymerization with chiral catalysts: New opportunities for stereocontrol using polymer exchange mechanisms. J. Am. Chem. Soc. 2002, 124, 1316-1326.
47. Lin, M.-H.; RajanBabu, T. V. Ligand-assisted rate acceleration in transacylation by a yttrium-salen complex. Demonstration of a conceptually new strategy for metal-catalyzed kinetic resolution of alcohols. Org. Lett. 2002, 4, 1607-1610.
48. Chisholm, M. H.; Zhou, Z. The Ohio State University, Columbus, OH. Unpublished results, 2004.
49. 3-L)MOR, where L = trispyrazolyl- and trisindazolylborate ligands. J. Am. Chem. Soc. 2000, 122, 11845-11854.
50. Bero, M.; Dobrzynski, P.; Kasperczyk, J. Synthesis of disyndiotactic polylactide. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 4038-4042.
51. Wisniewski, M.; Le Borgne, A.; Spassky, N. Synthesis and properties of (d)- and (l)-lactide stereocopolymers using the system achiral Schiff’s base/aluminum methoxide as initiator. Macromol. Chem. Phys. 1997, 198, 1227-1238.
52. Nomura, N.; Ishii, R.; Akakura, M.; Aoi, K. Stereoselective ring-opening polymerization of racemic lactide using aluminum-achiral ligand complexes: Exploration of a chain-end control mechanism. J. Am. Chem. Soc. 2002, 124, 5938-5939.
53. Tang, Z.; Chen, X.; Pang, X.; Yang, Y.; Zhang, X.; Jing, X. Stereoselective polymerization of raclactide using a monoethylaluminum Schiff base complex. Biomacromolecules 2004, 5, 965-970.
54. Hormnirun, P.; Marshall, E. L.; Gibson, V. C.; White, A. J. P.; Williams, D. J. Remarkable stereocontrol in the polymerization of racemic lactide using aluminum initiators supported by tetradentate aminophenoxide ligands. J. Am. Chem. Soc. 2004, 126, 2688-2689.
55. Chisholm, M. H.; Lin, C.-C.; Gallucci, J. C.; Ko, B.-T. Binolate complexes of lithium, zinc, aluminium, and titanium; preparations, structures, and studies of lactide polymerization. J. Chem. Soc., Dalton Trans. 2003, 406-412.
56. Chisholm, M. H.; Gallucci, J. C.; Phomphrai, K. Well-defined calcium initiators for lactide polymerization. Inorg. Chem. 2004, 43, 6717-6725.
57. Cheng, M.; Attygalle, A. B.; Lobkovsky, E. B.; Coates, G. W. Single-site catalysts for ring-opening polymerization: Synthesis of heterotactic poly(lactic acid) from rac-lactide. J. Am. Chem. Soc. 1999, 121, 11583-11584.
58. 3)(THF). Comments on single site catalysts for ring-opening polymerization of lactides. J. Chem. Soc., Dalton Trans. 2001, 222-224.
59. 2. A comparative study. Inorg. Chem. 2002, 41, 2785-2794.
60. Chisholm, M. H.; Phomphrai, K. Conformational effects in β-diiminate ligated magnesium and zinc amides. Solution dynamics and lactide polymerization. Inorg. Chim. Acta. 2003, 350, 121-125.
61. Dove, A. P.; Gibson, V. C.; Marshall, E. L.; White, A. J. P.; Williams, D. J. A well defined tin(II) initiator for the living polymerisation of lactide. Chem. Commun. 2001, 283-284.
62. Cai, C.-X.; Amgoune, A.; Lehmann, C.W.; Carpentier, J.-F. Stereoselective ring-opening polymerization of racemic lactide using alkoxy-amino-bis(phenolate) group 3 metal complexes. Chem. Commun.2004, 330-331.
63. Jensen, T. R.; Breyfogle, L. E.; Hillmyer, M. A.; Tolman, W. B. Stereoselective polymerization of d, l-lactide using N-heterocyclic carbene based compounds. Chem. Commun. 2004, 2504-2505.
64. von Schenck, H.; Ryner, M.; Albertsson, A.-C.; Svensson, M. Ring-opening polymerization of lactones and lactides with Sn(IV) and Al(III) initiators. Macromolecules 2002, 35, 1556-1562.
65. Marshall, E. L.; Gibson, V. C.; Rzepa, H. S. A computational analysis of the ring-opening polymerization of rac-lactide initiated by single-site β-diketiminate metal complexes: Defining the mechanistic pathway and the origin of stereocontrol. J. Am. Chem. Soc. 2005, 127, 6048-6051.