Degradable "click" polyesters from erythritol having free hydroxyl groups

Polymer Degradation and Stability

Volumn 97, Issue 9, 2012, Pages 1662-1670

  Bueno, Manuel ^a   Molina, Inmaculada ^a   Galbis, Juan A ^a  

^a UNIVERSITY OF SEVILLE   (Spain)

Author keywords

Click polymerization; Hydrolytic degradation; Hydrophilic polymers; Polyesters; Water soluble polymers

Indexed keywords

DEGRADATION STUDY; DISTILLED WATER; ESTER LINKAGES; FREE HYDROXYL GROUPS; HYDROLYTIC DEGRADATION; HYDROPHILIC POLYMERS; IR AND NMR SPECTROSCOPY; POLYADDITION; POLYMER CHAINS; SALT SOLUTION; THERMAL STUDY; WATERSOLUBLE POLYMERS; WEIGHT-AVERAGE MOLECULAR WEIGHT;

DEGRADATION; ESTERS; HYDROPHILICITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYESTERS; POLYMERIZATION;

POLYMERS;

EID: 84864613023     PISSN: 01413910     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.polymdegradstab.2012.06.020     Document Type: Article

References (42)

1. J.A. Galbis, and M.G. García-Martín M.N. Belgacem, A. Gandini, Monomers, oligomers, polymers and composites from renovable resources 2008 Elsevier Oxford (UK) 147 176
2. J.A. Galbis, and M.G. García-Martín Synthetic polymers from readily available monosaccharides Top Curr Chem 295 2010 147 176
3. K. Marcincinova-Benabdillah, J. Coudane, M. Boustta, and M. Vert Synthesis and characterization of novel degradable polyesters derived from d-gluconic and glycolic acids Macromolecules 32 1999 8774 8780 (Pubitemid 30533934)
4. H.C. Kolb, M.G. Finn, and K.B. Sharpless Click chemistry: diverse chemical function from a few good reactions Angew Chem Int Ed 40 2001 2004 2021
5. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless A stepwise Huisgen cycloaddition process: copper(I)-catalysed regioselective "ligation" of azides and terminal alkynes Angew Chem Int Ed 41 2002 2596 2599 (Pubitemid 34803480)
6. C.W. Tornoe, C. Christensen, and M. Meldal Peptidotriazoles on solid phase:[1,2,3]-triazoles by regiospecific copper(I)-catalysed 1,3-dipolar cycloadditions of terminal alkynes to azides J Org Chem 67 2002 3057 3064 (Pubitemid 34457265)
7. S. Hvilsted Facile design of biomaterials by 'click' chemistry Polym Int 61 2012 485 494
8. C.R. Becer, R. Hoogenboom, and U.S. Schubert Click chemistry beyond metal-catalysed cycloaddition Angew Chem Int Ed 47 2009 4900 4908
9. J.-F. Lutz Copper-free azide-alkyne cycloadditions: new insights and perspectives Angew Chem Int Ed 47 2008 2182 2184
10. J.-F. Lutz, and Z. Zarafshani Efficient construction of therapeutics, bioconjugates, biomaterials and bioactive surfaces using azide-alkyne "click" chemistry Adv Drug Deliv Rev 60 2008 958 970
11. G.W. Goodall, and W. Hayes Advances in cycloaddition polymerizations Chem Soc Rev 35 2006 280 312 (Pubitemid 43327148)
12. Y. Nagao, and A. Takasu "Click polyester": synthesis of polyesters containing triazole units in the main chain via safe and rapid "click" chemistry and their properties J Polym Sci Part A: Polym Chem 48 2010 4207 4218
13. S. Binauld, F. Boisson, T. Hamaide, J.-P. Pascault, E. Drockenmuller, and E. Fleury Kinetic study of copper(I)-catalysed click chemistry step-growth polymerization J Polym Sci Part A: Polym Chem 46 2008 5506 5517
14. R.M. Meudtner, and S. Hecht Responsive backbones based on alternating triazole-pyridine/benzene copolymers: from helically folding polymers to metallosupramolecularly crosslinked gels Macromol Rapid Commun 29 2008 347 351
15. J.A. Johnson, M.G. Finn, J.T. Koberstein, and N.J. Turro Construction of linear polymers, dendrimers, networks, and other polymeric architectures by copper-catalysed azide-alkyne cycloaddition "click" chemistry Macromol Rapid Commun 29 2008 1052 1072
16. X.-M. Liu, A. Thakur, and D. Wang Efficient synthesis of linear multifunctional poly(ethylene glycol) by copper(I)-catalysed Huisgen 1,3-dipolar cycloaddition Biomacromolecules 8 2007 2653 2658 (Pubitemid 47516911)
17. A. Qin, C.K.W. Jim, W. Lu, J.W.Y. Lam, M. Häussler, and Y. Dong Click polymerization: facile synthesis of functional poly(aroyltriazole)s by metal-free, regioselective 1,3-dipolar polycycloaddition Macromolecules 40 2007 2308 2317 (Pubitemid 46608256)
18. L. Wan, J. Tian, J. Huang, Y. Hu, F. Huang, and L. Du Synthesis and characterization of a novel polytriazole J Macromol Sci Part A: Pure Appl Chem 44 2007 175 181 (Pubitemid 44927202)
19. Y. Zhu, Y. Huang, W.-D. Meng, H. Li, and F.-L. Qing Novel perfluorocyclobutyl (PFCB)-containing polymers formed by click chemistry Polymer 47 2006 6272 6279 (Pubitemid 44189457)
20. S. Srinivasachari, Y. Liu, G. Zhang, L. Prevette, and T.M. Reineke Trehalose click polymers inhibit nanoparticle aggregation and promote pDNA delivery in serum J Am Chem Soc 128 2006 8176 8184 (Pubitemid 43967762)
21. D.M. Mizrahi, M. Omer-Mizrahi, J. Goldshtein, N. Askinadze, and S. Margel Novel poly(ethylene glycol) monomers bearing diverse functional groups J Polym Sci Part A: Polym Chem 48 2010 5468 5478
22. K.Y. Lee, and S.H. Yuk Polymeric protein delivery systems Polym Sci 32 2007 669 697 (Pubitemid 46977433)
23. G. Pasut, M. Sergi, and F.M. Veronese Anti-cancer PEG-enzymes: 30 years old, but still a current approach Adv Drug Deliv Rev 60 2008 69 78 (Pubitemid 350181167)
24. H.R. Kricheldorf "Sugar diols" as building blocks of polycondensates J Macromol Sci Part C: Polym Rev C37 1997 599 631 (Pubitemid 127569147)
25. R. Quintana, A. Martinez de Ilarduya, A. Alla, and S. Muñoz-Guerra Polyterephthalates made from ethylene glycol, 1,4-cyclohexanedimethanol, and isosorbide J Polym Sci Part A: Polym Chem 49 2011 2252 2260
26. J.F. Lutz 1,3-Dipolar cycloadditions of azides and alkynes: a universal ligation tool in polymer and materials science Angew Chem Int Ed 46 2007 1018 1025
27. L. Wang, Y. Song, R. Gyanda, R. Sakhuja, N.K. Meher, and S. Hanci Preparation and mechanical properties of crosslinked 1,2,3-triazole-polymers as potential propellant binders J Appl Polym Sci 117 2010 2612 2621
28. A.L. Katritzky, N.K. Meher, S. Hanci, R. Gyanda, S. Tala, and S. Mathai Preparation and characterization of 1,2,3-triazole-cured polymers from endcapped azides and alkynes J Polym Sci Part A: Polym Chem 46 2008 238 256
29. C.M. Thompson, and P.M. Hergenrother Phenylethynyl terminated arylene ether oxadiazole and triazole oligomers and their cured polymers High Perform Polym 13 2001 313 322 (Pubitemid 34043897)
30. Reed R. Triazole cross-linked polymers. US Patent; 2000; 6103029.
31. B. Trachli, M. Keddam, H. Takenouti, and A. Srhiri Protective effect of electropolymerized 3-amino 1,2,4-triazole towards corrosion of copper in 0.5 M NaCl Corros Sci 44 2002 997 1008 (Pubitemid 34170176)
32. P.G. Cao, J.L. Yao, J.W. Zheng, R.A. Gu, and Z.Q. Tian Comparative study of inhibition effects of benzotriazole for metals in neutral solutions as observed with surface-enhanced Raman spectroscopy Langmuir 18 2002 100 104 (Pubitemid 35382284)
33. M.M. El-Naggar Bis-triazole as a new corrosion inhibitor for copper in sulfate solution. A model for synergistic inhibition action J Mat Sci 35 2000 6189 6195 (Pubitemid 32076441)
34. D.A. Díaz, S. Punna, P. Holzer, A.K. McPherson, K.B. Sharpless, and V.V. Fokin Click chemistry in materials synthesis. 1. Adhesive polymers from copper-catalysed azide-alkyne cycloaddition J Polym Sci Part A: Polym Chem 42 2004 4392 4403
35. H.C. Kolb, and K.B. Sharpless The growing impact of click chemistry on drug discovery Drug Discov Today 8 2003 1128 1137 (Pubitemid 37547919)
36. V. Glaçon, M. Benazza, A. El Anzi, D. Beaupère, and G. Demailly Synthesis of α,ω-diazidoalditol derivatives via both bis- or tris-cyclic sulfites and peracetylated α,ω-dibromoalditols as bielectrophilic intermediates J Carbohydr Chem 23 2004 95 110 (Pubitemid 44161418)
37. A.R. Katritzky, S.K. Singh, N.K. Meher, J. Doskocz, K. Suzuki, and R. Jiang Triazole-oligomers by 1,3-dipolar cycloaddition Arkivoc 5 2006 43 62 (Pubitemid 43356319)
38. L. Balas, B. Jousseaume, and B. Langwost Improved preparation of aliphatic propynoic esters Tetrahedron Lett 30 1989 4525 4526
39. C. Besset, J.-P. Pascault, E. Fleury, E. Drockenmuller, and J. Bernard Structure-properties relationship of biosourced stereocontrolled polytriazoles from click chemistry step growth polymerization of diazide and dialkyne dianhydrohexitols Biomacromolecules 11 2010 2797 2803
40. A. Qin, L. Tang, J.W.Y. Lam, C.K.W. Jim, Y. Yu, and H. Zhao Metal-free click polymerization: synthesis and photonic properties of poly(aroyltriazole)s Adv Funct Mater 19 2009 1891 1900
41. J.A. Codelli, J.M. Baskin, N.J. Agard, and C.R. Bertozzi Second-generation difluorinated cyclooctynes for copper-free click chemistry J Am Chem Soc 130 2008 11486 11493
42. D. Braun, H. Chedron, and W. Kern Praktikum der Makromolekularen Organischen Chemie 1966 Alfred Huthig Verlag Heidelberg