A strategy for control of "random" copolymerization of lactide and glycolide: Application to synthesis of PEG- b -PLGA block polymers having narrow dispersity

Macromolecules

Volumn 44, Issue 18, 2011, Pages 7132-7140

  Qian, Haitao ^a   Wohl, Adam R ^a   Crow, Jordan T ^a   MacOsko, Christopher W ^a   Hoye, Thomas R ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE; BATCH POLYMERIZATIONS; BIODEGRADABLE COPOLYMERS; BIOMEDICAL APPLICATIONS; BIOMEDICAL INVESTIGATIONS; CYCLIC ESTERS; GLYCOLIDE; GLYCOLIDE MONOMERS; HIGH TEMPERATURE; LACTIDES; MACROINITIATORS; NARROW DISPERSITY; NOVEL STRATEGIES; ORGANOCATALYSTS; POLY(LACTIC-CO-GLYCOLIC ACID); POLYDISPERSITY INDICES; POLYMER PRODUCTS; POLYMERIZATION KINETICS; RANDOM COPOLYMER; REACTION CONDITIONS; ROOM TEMPERATURE; SEMI-BATCH POLYMERIZATION;

BIODEGRADABLE POLYMERS; BLOCK COPOLYMERS; CATALYSTS; COPOLYMERIZATION; ETHYLENE; FUNCTIONAL POLYMERS; GLYCOLS; MEDICAL APPLICATIONS; MONOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYDISPERSITY; POLYETHYLENE OXIDES; RING OPENING POLYMERIZATION; SYNTHESIS (CHEMICAL); THERMODYNAMIC PROPERTIES; TIN;

POLYETHYLENE GLYCOLS;

EID: 80053010066     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma201169z     Document Type: Article

References (39)

1. Jerome, C.; Lecomte, P. Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization Adv. Drug Delivery Rev. 2008, 60, 1056-1076
2. Astente, C. E.; Sabliov, C. M. Synthesis and characterization of PLGA nanoparticles J. Biomater. Sci., Polym. Ed. 2006, 17, 247-289 (Pubitemid 47279194)
3. Albertsson, A. C.; Varma, I. K. Recent developments in ring opening polymerization of lactones for biomedical applications Biomacromolecules 2003, 4, 1466-1486 (Pubitemid 37460959)
4. Mohamed, F.; Van der Walle, C. F. Engineering biodegradable polyester particles with specific drug targeting and drug release properties J. Pharm. Sci. 2008, 97, 71-87
5. Middleton, J. C.; Tipton, A. J. Synthetic biodegradable polymers as orthopedic devices Biomaterials 2000, 21, 2335-2346
6. Drumright, R. E.; Gruber, P. R.; Henton, D. E. Polylactic acid technology Adv. Mater. 2000, 12, 1841-1846 (Pubitemid 32090435)
7. Chu, C. C. Biodegradable polymeric biomaterials: an updated overview. In Biomaterials; Wong, J. Y.; Bronzino, J. D., Eds.; CRC Press: Boca Raton, FL, 2007; pp 6/1-6/22.
8. Vert, M. Polyglycolide and copolyesters with lactide Biopolymers 2002, 4, 179-202
9. Stjerndahl, A.; Wistrand, A. F.; Albertsson, A. C. Industrial utilization of tin-initiated resorbable polymers: synthesis on a large scale with a low amount of initiator Biomacromolecules 2007, 8, 937-940 (Pubitemid 46488475)
10. Li, J.; Stayshich, R. M.; Meyer, T. Y. Exploiting Sequence to Control the Hydrolysis Behavior of Biodegradable PLGA Copolymers J. Am. Chem. Soc. 2011, 133, 6910-6913
11. Dechy-Cabaret, O.; Martin-Vaca, B.; Bourissou, D. Controlled ring-opening polymerization of lactide and glycolide Chem. Rev. 2004, 104, 6147-6176 (Pubitemid 40025736)
12. Dong, C.-M.; Qiu, K.-Y.; Gu, Z.-W.; Feng, X.-D. Synthesis of poly(d, l -lactic acid-alt-glycolic acid) from d, l -3-methylglycolide J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 4179-4184 (Pubitemid 32024031)
13. Kreiser-Saunders, I.; Kricheldorf, H. R. Polylactones. Part 39. Zn lactate-catalyzed copolymerization of l -lactide with glycolide or ε-caprolactone Macromol. Chem. Phys. 1998, 199, 1081-1087 (Pubitemid 128477783)
14. 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 (Pubitemid 35166706)
15. Barakat, I.; Dubois, P.; Jérôme, R.; Teyssié, P. Living polymerization and selective end functionalization of ε-caprolactone using zinc alkoxides as initiators Macromolecules 1991, 24, 6542-6545
16. Baran, J.; Duda, A.; Kowalski, A.; Szymanski, R.; Penczek, S. Quantitative comparison of selectivities in the polymerization of cyclic esters Macromol. Symp. 1997, 123, 93-101 (Pubitemid 127477401)
17. 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 (Pubitemid 34169138)
18. Shen, Y.; Shen, Z.; Shen, J.; Zhang, Y.; Yao, K. Characteristics and mechanism of ε-caprolactone polymerization with rare earth halide systems Macromolecules 1996, 29, 3441-3446 (Pubitemid 126542286)
19. 5(DME)] initiator for the living ring-opening polymerization of ε-caprolactone and δ-valerolactone Macromolecules 2001, 34, 8649-8653 (Pubitemid 34011389)
20. Chamberlin, B. M.; Jazdzewski, B. A.; Pink, M.; Hillmyer, M. A.; Tolman, W. B. Controlled polymerization of dl -lactide and ε-caprolactone by structurally well-defined alkoxo-bridged di- and triyttrium(III) complexes Macromolecules 2000, 33, 3970-3977
21. Albertsson, A. C.; Srivastava, R. K. Recent developments in enzyme-catalyzed ring-opening polymerization Adv. Drug Delivery Rev. 2008, 60, 1077-1093
22. Nederberg, F.; Connor, E. F.; Möller, M.; Glauser, T.; Hedrick, J. L. New paradigms for organic catalysts: the first organocatalytic living polymerization Angew. Chem., Int. Ed. 2001, 40, 2712-2715 (Pubitemid 32691726)
23. Dove, A. P.; Pratt, R. C.; Lohmeijer, B. G. G.; Culkin, D. A.; Hagberg, E. C.; Nyce, G. W.; Waymouth, R. M.; Hedrick, J. L. N- Heterocyclic carbenes: effective organic catalysts for living polymerization Polymer 2006, 47, 4018-4025 (Pubitemid 43767404)
24. 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 (Pubitemid 34268563)
25. Zhang, L.; Nederberg, F.; Messman, J. M.; Pratt, R. C.; Hedrick, J. L.; Wade, C. G. Organocatalytic stereoselective ring-opening polymerization of lactide with dimeric phosphazene bases J. Am. Chem. Soc. 2007, 129, 12610-12611 (Pubitemid 350004440)
26. Lohmeijer, B. G. G.; Pratt, R. C.; Leibfarth, F.; Logan, J. W.; Long, D. A.; Dove, A. P.; Nederberg, F.; Choi, J.; Wade, C.; Waymouth, R. M.; Hedrick, J. L. Guanidine and amidine organo-catalysts for ring-opening polymerization of cyclic esters Macromolecules 2006, 39, 8574-8583 (Pubitemid 46079620)
27. Dong, J.; Jiang, S.; Ping, Q. Development of injectable biodegradable in-situ forming gel implants Yaoxue Jinzhan 2007, 31, 110-113
28. Avgoustakis, K. Pegylated poly(lactide) and poly(lactide-co-glycolide) nanoparticles: Preparation, properties and possible applications in drug delivery Curr. Drug Delivery 2004, 1, 321-333
29. Huh, K. M.; Cho, Y. W.; Park, K. PLGA-PEG block copolymers for drug formulations Drug Delivery Technol. 2003, 42, 44-49
30. 1H NMR: a case of changing stereospecificity Macromolecules 1998, 21, 1487-1497
31. Kricheldorf, H. R.; Kreiser, I. Polylactones, 11. Cationic copolymerization of glycolide with l,l -dilactide Makromol. Chem. 1987, 188, 1861-1873
32. Gilding, D. K.; Reed, A. M. Biodegradable polymers for use in surgery - polyglycolic/poly(lactic acid) homo- and copolymers: 1 Polymer 1979, 20, 1459-1464 (Pubitemid 10435422)
33. Dotson, N. A.; Galván, R.; Laurence, R. L.; Tirrell, M. Reactor Configuration. In Polymerization Process Modeling; VCH Publishers, Inc.: New York, 1996; pp 259-303.
34. Huffman, K. R.; Casey, D. J. Effect of carboxyl end groups on polyglycolic acid J. Polym. Sci., Polym. Chem. Ed. 1985, 23, 1939-1954 (Pubitemid 15542517)
35. Khandpur, A. K.; Förster, S.; Bates, F. S.; Hamley, I W.; Ryan, A. J.; Bras, W.; Almdal, K.; Mortensen, K. Polyisoprene-polystyrene diblock copolymer phase diagram near the order-disorder transition Macromolecules 1995, 28, 8796-8806
36. Bandrup, J.; Immergut, E. H.; Grulke, E. A.; Abe, A.; Bloch, D. R. Polymer Handbook, 4 th ed.; John Wiley & Sons, Inc.: New York, 1999.
37. Kricheldorf, H. R.; Mang, T.; Jonte, J. M. Polylactones. 1. Copolymerization of glycolide and ε-caprolactone Macromolecules 1984, 17, 2173-2181
38. Grujpma, D. W.; Nijenhuis, A. J.; Pennings, A. J. Synthesis and hydrolytic degradation behaviour of high-molecular-weight l -lactide and glycolide copolymers Polymer 1990, 31, 2201-2206
39. Odian, G. Principles of Polymerization, 4 th ed.; Wiley-Interscience: New York, 2004; p 470.