Ring-opening copolymerization of (R,S)-β-butyrolactone and ε-caprolactone using sodium hydride as initiator

Express Polymer Letters

Volumn 4, Issue 7, 2010, Pages 431-441

  Monsalve, M ^a   Contreras, J M ^a   Laredo, E ^b   Lopez Carrasquero F ^a  

^a FACULTAD DE CIENCIAS   (Venezuela)

^b UNIVERSIDAD SIMÓN BOLÍVAR   (Venezuela)

Author keywords

Butyrolactone; caprolactone; Biodegradable polymers; Block copolymers; Sodium hydride

Indexed keywords

EID: 77954049569     PISSN: 1788618X     EISSN: None     Source Type: Journal    
DOI: 10.3144/expresspolymlett.2010.54     Document Type: Article

References (52)

1. Vert M.: Bioresorbable polymers for temporary therapeutic applications. Die Angewandte Makromolekulare Chemie, 166, 155-168 (1989). DOI: 10.1002/apmc.1989.051660111
2. Dobrzynski P.: Synthesis of biodegradable copolymers with low-toxicity zirconium compounds. III. Synthesis and chain-microstructure analysis of ter-polymer obtained from L-lactide, glycolide, and ε-caprolactone initiated by zirconium(IV) acetylacetonate. Journal of Polymer Science Part A: Polymer Chemistry, 40, 3129-3143 (2002). DOI: 10.1002/pola.10401
3. Ashammakhi N., Mäkelä E. A., Vihtonen K., Rokkanen P., Törmälä P.: Effect of self-reinforced polyglycolide membranes on cortical bone: An experimental study on rats. Journal of Biomedical Materials Research, 29, 687-694 (1995). DOI: 10.1002/jbm.820290603
4. Stridsberg K., Albertsson A.C.: Controlled ring-opening polymerization of L-lactide and 1,5-dioxepan-2- one forming a triblock copolymer. Journal of Polymer Science Part A: Polymer Chemistry, 38, 1774-1784 (2000). DOI: 10.1002/(SICI)1099-0518(20000515)38:10 <1774:: AID-POLA620>3.0.CO;2-F
5. Vanhoorne P., Dubois P., Jerome R., Teyssie P.: Macromolecular engineering of polylactones and polylactides. 7. Structural analysis of copolyesters of ε-caprolactone and L- or D,L-lactide initiated by triisopropoxyaluminum. Macromolecules, 25, 37-44 (1992). DOI: 10.1021/ma00027a008
6. Kricheldorf H. R., Rost S.: A-B-A-triblock and multiblock copolyesters prepared from ε-caprolactone, glycolide and L-lactide by means of bismuth subsalicylate. Polymer, 46, 3248-3256 (2005). DOI: 10.1016/j.polymer.2005.02.004
7. Hiki S., Miyamoto M., Kimura Y.: Synthesis and characterization of hydroxy-terminated RS]-poly(3-hydroxybutyrate) and its utilization to block copolymerization with L-lactide to obtain a biodegradable thermoplastic elastomer. Polymer, 41, 7369-7379 (2000). DOI: 10.1016/S0032-3861(00)00086-0
8. Chen C., Peng S., Wu H., Zhuang Y., Chen X., Dong L., Feng Z.: Synthesis and characterizacion of poly(β-hydroxibutyrate) and poly(ε-caprolactone) copolyesters by transesterification. Journal of Polymer Science Part B: Polymer Physics, 40, 1893-1903 (2002). DOI: 10.1002/polb.10242
9. Zhong Z., Yu D., Meng F., Gan Z., Ping X.: Controlled synthesis of L-lactide-b-ε-caprolactone block copolymers using a rare earth complex as catalyst. Polymer Journal, 31, 633-636 (1999). DOI: 10.1295/polymj.31.633
10. Fukuzaki H., Yoshida M., Asano M., Kumakura M., Mashimo T., Yuasa H., Imai K., Yamanaka H.: Synthesis of low-molecular-weight copoly(L-lactic acid/ε-caprolactone) by direct copolycondensation in the absence of catalysts, and enzymatic degradation of the polymers. Polymer, 31, 2006-2014 (1990). DOI: 10.1016/0032-3861(90)90031-S
11. Vivas M., Mejías N., Contreras J.: Ring-opening polymerization of lactones initiated by diphenylzinc-coinitiator systems. Polymer International, 52, 1005-1009 (2003). DOI: 10.1002/pi.1183
12. Abe H., Matsubara I., Doi Y., Hori Y., Yamaguchi A.: Physical properties and enzymic degradability of poly(3-hydroxybutyrate) stereoisomers with different stereoregularities. Macromolecules, 27, 6018-6025 (1994). DOI: 10.1021/ma00099a013
13. Kricheldorf H. R., Lee S-R.: Polylactones. 35. Macrocyclic and stereoselective polymerization of β-D,L-butyrolactone with cyclic dibutyltin initiators. Macromolecules, 28, 6718-6725 (1995). DOI: 10.1021/ma00124a004
14. Kohn F. E., Van Den Berg J., Van De Ridder G.: The ring-opening polymerization of D,L-lactide in the melt initiated with tetraphenyltin. Journal of Applied Polymer Science, 29, 4265-4277 (1984). DOI: 10.1002/app.1984.070291255
15. Grijpma D. W., Pennings A. J.: Polymerization temperature effects on the properties of L-lactide and ε-caprolactone copolymers. Polymer Bulletin, 25, 335-341 (1991). DOI: 10.1007/BF00316903
16. Storey R. F., Herring K. R., Hoffman D. C.: Hydroxy-terminated poly(ε-caprolactone-co-δ-valerolactone) oligomers: Synthesis, characterization, and polyurethane network formation. Journal of Polymer Science Part A: Polymer Chemistry, 29, 1759-1777 (1991). DOI: 10.1002/pola.1991.080291209
17. Kricheldorf H. R., Lee S., Scharnagl N.: Polylactones. 28. Syndiotactic poly(β-D,L-hydroxybutyrate) by ring-opening polymerization of β-D,L-Butyrolactone with butyltin methoxides. Macromolecules, 27, 3139-3146 (1994). DOI: 10.1021/ma00090a005
18. Kricheldorf H.R., Eggerstedt S.: Polylactones: 41. Polymerization of β-D,L-Butyrolactone with dialkyltinoxides as initiators. Macromolecules, 30, 5693-5697 (1997). DOI: 10.1021/ma970244c
19. Nakayama A., Kawasaki N., Maeda Y., Arvanitoyannis I., Aiba S., Yamamoto N.: Study of biodegradability of poly(δ-valerolactone-co-L-lactide)s. Journal of Applied Polymer Science, 66, 741-748 (1997). DOI: 10.1002/(SICI)1097-4628(19971024)66:4<741:: AID-APP14>3.0.CO;2-U
20. Nakayama A., Kawasaki N., Aiba S., Maeda Y., Arvanitoyannis I., Yamamoto N.: Synthesis and biodegradability of novel copolyesters containg γ-butyrolactone units. Polymer, 39, 1213-1222 (1998). DOI: 10.1016/S0032-3861(97)00401-1
21. Kricheldorf H. R., Bornhorst K., Hachmann-Thiessen H.: Bismuth(III) n-hexanoate and Tin (II) 2-ethyl-hexanoate initiated copolymerizations of ε-caprolac-tone and L-lactide. Macromolecules, 38, 5017-5024 (2005). DOI: 10.1021/ma047873o
22. Piao L., Deng M., Chen X., Jiang L., Jing X.: Ring-opening of ε-caprolactone and L-lactide using organic aminocalcium catalyst. Polymer, 44, 2331-2336 (2003). DOI: 10.1016/s0032-3861(03)00118-6
23. Zhong Z., Ankoné M., Dijkstra P. J., Birg C., Wester-hausen M., Feijen J.: Calcium methoxide initiated ring-opening polymerization of ε-caprolactone and L-lactide. Polymer Bulletin, 46, 51-57 (2001). DOI: 10.1007/s002890170088
24. Vivas M., Contreras J.: Ring-opening polymerization of ε-caprolactone initiated by diphenylzinc. European Polymer Journal, 39, 43-47 (2003). DOI: 10.1016/S0014-3057(02)00190-8
25. Contreras J., Dávila D.: Ring-opening copolymerization of L-lactide with ε-caprolactone initiated by diphenylzinc. Polymer International, 55, 1049-1056 (2006). DOI: 10.1002/pi.2050
26. Dobrzynski P.: Synthesis of biodegradable copolymers with low-toxicity zirconium compounds. II. Copolymerization of glycolide with ε-caprolactone initiated by zirconium(IV) acetylacetonate and zirconium(IV) chloride. Journal of Polymer Science Part A: Polymer Chemistry, 40, 1379-1394 (2002). DOI: 10.1002/pola.10222
27. Kurcok P., Matuszowics A., Jedlin ́ski Z.: Anionic polymerization of β-lactones initiated with potassium hydride. A convenient route to polyester macro-monomers. Macromolecular Rapid Communication, 16, 201-206 (1995). DOI: 10.1002/marc.1995.030160308
28. Kurcok P., Kowalczuk M., Hennek K., Jedlinsky Z.: Anionic polymerization of β-lactones initiated with alkali-metal alkoxides: Reinvestigation of the polymerization mechanism. Macromolecules, 25, 2017-2020 (1992). DOI: 10.1021/ma00033a027
29. Kurcok P., Dubois P., Sikorska W., Jedlinsky Z., Jèrôme R.: Macromolecular engineering of lactones and lactides. 24. Controlled synthesis of (R,S)-β-butyrolactone-b-ε-caprolactone block copolymers by anionic and coordination polymerization. Macromolecules, 30, 5591-5595 (1997). DOI: 10.1021/ma970212p
30. Liu K., Goh S., Li J.: Controlled synthesis and characterizations of amphiphilic poly[(R,S)-3-hydroxybutyrate]-poly(ethylene glycol)-poly[(R,S)-3-hydroxybutyrate] triblock copolymers. Polymer, 49, 732-741 (2008). DOI: 10.1016/j.polymer.2007.12.017
31. Adamus G., Kowalczuk M.: Anionic ring-opening polymerization of β-alkoxymethyl-substituted β-lac-tones. Biomacromolecules, 9, 696-703 (2008). DOI: 10.1021/bm701077v
32. Yu G., Marchessault R. H.: Characterization of low molecular weight poly(β-hydroxybutyrate)s from alkaline and acid hydrolysis. Polymer, 41, 1087-1098 (2000). DOI: 10.1016/S0032-3861(99)00230-X
33. Jedlin ́sky Z., Kowalczuk M., Kurcok P.: Polymerization of β-lactones initiated by alkali metal naphthalenides. A convenient route to telechelic polymers. Journal of Macromolecular Science Part A, 29, 1223-1230 (1992). DOI: 10.1080/10601329208054152
34. Duda A.: Anionic polymerization of 4-methyl-2-oxetanone (β-butyrolactone). Journal of Polymer Science Part A: Polymer Chemistry, 30, 21-29 (1992). DOI: 10.1002/pola.1992.080300103
35. Kurcok P., Matuszowicz A., Jedliński Z., Kricheldorf H. R., Dubois P., Jèrôme R.: Substituent effect in anionic polymerization of β-lactones initiated by alkali metal alkoxides. Macromolecular Rapid Communication, 16, 513-519 (1995). DOI: 10.1002/marc.1995.030160709
36. Jedlinsky Z., Kowalczuk M., Kurcok P., Adamus G., Matuszuwicz A., Sikorska W., Gross R. A., Xu J., Lenz R. W.: Stereochemical control in the anionic polymerization of β-Butyrolactone initiated with alkali-metal alkoxides. Macromolecules, 29, 3773-3777 (1996). DOI: 10.1021/ma951888s
37. iPr)3. Polymer International, 41, 479-485 (1999). DOI: 10.1002/(SICI)1097-0126(199612)41:4<479::AID-PI652>3.0.CO;2-w.
38. Kurcok P., Smiga M., Jedlinsky Z.: β-butyrolactone polymerization initiated with tetrabutylammonium carboxylates: A novel approach to biomimetic polyester synthesis. Journal of polymer Science Part A: Polymer Chemistry, 40, 2184-2189 (2002). DOI: 10.1002/pola.10285
39. Arkin A. H., Hazet B., Adamus G., Kuwalczuk M., Jedlin ́sky Z., Lenz R. W.: Synthesis of poly(2-methyl- 3-hydroxyoctanoate) via anionic polymerization of α- methyl-β-pentyl-β-propiolactone. Biomacromolecules, 2, 623-627 (2001). DOI: 10.1021/bm015528q
40. Kawalec M., S ́miga-Matuszowicz M., Kurcok P.: Counterion and solvent effects on the anionic polymerization of β-Butyrolactone initiated with acetic acid salts. European Polymer Journal, 44, 3556-3563 (2008). DOI: 10.1016/j.eurpolymj.2008.09.008
41. Kricheldorf H. R., Mang T., Jonté J. M.: Polylactones. 1. Copolymerizations of glycolide and ε-Caprolactone. Macromolecules, 17, 2173-2181 (1984). DOI: 10.1021/ma00140a051
42. Aoyagi Y., Yamashita K., Doi Y.: Thermal degradation of poly[(R)-3-hydroxybutyrate], poly[ε-Caprolactone], and poly[(S)-lactide]. Polymer Degradation and Stability, 76, 53-59 (2002). DOI: 10.1016/S0141-3910(01)00265-8
43. Gonzalez A., Irusta L., Fernández-Berridi M. J., Iriarte M., Iruin J. J.: Application of pyrolysis/gas chromatography/Fourier transform infrared spectroscopy and TGA techniques in the study of thermal degradation of poly (3-hydroxybutyrate). Polymer Degradation and Stability, 87, 347-354 (2005). DOI: 10.1016/j.polymdegradstab.2004.09.005
44. Ariffin H., Nishida H., Shirai Y., Hassan M. A.: Determination of multiple thermal degradation mechanisms of poly(3-hydroxybutyrate). Polymer Degradation and Stability, 93, 1433-1439 (2008). DOI: 10.1016/j.polymdegradstab.2008.05.020
45. Kawalec M., Adamus G., Kurcok P., Kowalczuk M., Foltran I., Focarete M. L., Scandola M.: Carboxylate- induced degradation of poly(3-hydroxybutyrate)s. Biomacromolecules, 8, 1053-1058 (2007). DOI: 10.1021/bm061155n
46. Pearce R., Marchessault R. H.: Multiple melting in blends of isotactic and atactic poly(β-hydroxybutyrate). Polymer, 35, 3990-3997 (1994). DOI: 10.1016/0032-3861(94)90285-2
47. Gunaratne L. M., Shanks R. A.: Multiple melting behaviour of poly(3-hydroxybutyrate-co-hydroxyvalerate) using step-scan DSC. European Polymer Journal, 41, 2980-2988 (2005). DOI: 10.1016/j.eurpolymj.2005.06.015
48. Yoo E. S., Im S. S.: Melting behavior of poly(butylenes succinate) during heating scan by DSC. Journal of Polymer Science Part B: Polymer Physics, 37, 1357-1366 (1999). DOI: 10.1002/(SICI)1099-0488(19990701)37:13 <1357::AID-POLB2>3.0.CO;2-Q
49. Bittiger H., Marchessault R. H., Niegisch W.D.: Crystal structure of poly-ε-Caprolactone. Acta crystallo-graphica, B26, 1923-1927 (1970). DOI: 10.1107/S0567740870005198
50. Herrera D., Zamora J-C., Bello A., Grimau M., Laredo E., Müller A. J., Lodge T.: Miscibility and crystallization in polycarbonate/poly(ε-Caprolactone) blends: Application of the self-concentration model. Macromolecules, 38, 5109-5120 (2005). DOI: 10.1021/ma050481c
51. Balsamo V., Newman D., Gouveia L., Herrera L., Grimau M., Laredo E.: Molecular dynamics and crystallization kinetics in PSMA14/PCL blends. Polymer, 47, 5810-5820 (2006). DOI: 10.1016/j.polymer.2006.06.019
52. Laredo E., Hernández M. C., Bello A., Grimau M., Müller A., Balsamo V.: Local and segmental dynamics in homopolymer and triblock copolymers with one semicrystalline block. Physical Review E, 65, 021807/1-021807/13 (2002). DOI: 10.1103/PhysRevE.65.021807