Amphiphilic conetworks and gels physically cross-linked via stereocomplexation of polylactide

Langmuir

Volumn 29, Issue 46, 2013, Pages 14307-14313

  Fan, Xiaoshan ^a   Wang, Mian ^b   Yuan, Du ^a   He, Chaobin ^a,c  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b XINXIANG MEDICAL UNIVERSITY   (China)

^c INSTITUTE OF MATERIALS RESEARCH AND ENGINEERING   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIPHILIC CONETWORKS; FREE RADICAL COPOLYMERIZATION; METHYL ESTERS; POLY-L-LACTIDE; RHEOLOGY PROPERTY; STEREOCOMPLEXATION; STEREOCOMPLEXES; SWELLING BEHAVIOR;

FREE RADICALS; HYDROPHOBICITY; POLYETHYLENE GLYCOLS;

COMPLEXATION;

MACROGOL DERIVATIVE; METHACRYLIC ACID DERIVATIVE; POLYESTER; POLYETHYLENE GLYCOL METHACRYLATE; POLYLACTIDE;

ARTICLE; CHEMICAL PHENOMENA; CHEMISTRY; GEL; STEREOISOMERISM;

GELS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; METHACRYLATES; POLYESTERS; POLYETHYLENE GLYCOLS; STEREOISOMERISM;

EID: 84888345826     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la403432y     Document Type: Article

References (57)

1. Chiellini, E.; Solaro, R. Biodegradable polymeric materials Adv. Mater. 1996, 8 (4) 305-313
2. Kricheldorf, H. R.; Berl, M.; Scharnagl, N. Poly(lactones). 9. Polymerization mechanism of metal alkoxide initiated polymerization of lactide and various lactones Macromolecules 1988, 21 (2) 286-293
3. Uhrich, K. E.; Cannizzaro, S. M.; Langer, R. S.; Shakesheff, K. M. Polymeric systems for controlled drug release Chem. Rev. 1999, 99 (11) 3181-3198
4. Ikada, Y.; Jamshidi, K.; Tsuji, H.; Hyon, S. H. Stereocomplex formation between enantiomeric poly(lactides) Macromolecules 1987, 20 (4) 904-906
5. Jamshidian, M.; Tehrany, E. A.; Imran, M.; Jacquot, M.; Desobry, S. Poly-lactic acid: Production, applications, nanocomposites, and release studies Compr. Rev. Food. Sci. Food Saf. 2010, 9 (5) 552-571
6. Luckachan, G. E.; Pillai, C. K. S. Biodegradable polymers- A review on recent trends and emerging perspectives J. Polym. Environ. 2011, 19 (3) 637-676
7. Slager, J.; Domb, A. J. Biopolymer stereocomplexes Adv. Drug Delivery Rev. 2003, 55 (4) 549-583
8. Tsuji, H. Poly(lactide) stereocomplexes: Formation, structure, properties, degradation, and applications Macromol. Biosci. 2005, 5 (7) 569-597
9. Fukushima, K.; Kimura, Y. Stereocomplexed polylactides (Neo-PLA) as high-performance bio-based polymers: their formation, properties, and application Polym. Int. 2006, 55 (6) 626-642
10. Kakuta, M.; Hirata, M.; Kimura, Y. Stereoblock polylactides as high-performance bio-based polymers Polym. Rev. 2009, 49 (2) 107-140
11. Sugai, N.; Yamamoto, T.; Tezuka, Y. Synthesis of orientationally isomeric cyclic stereoblock polylactides with head-to-head and head-to-tail linkages of the enantiomeric segments ACS Macro Lett. 2012, 1 (7) 902-906
12. Hiemstra, C.; Zhong, Z.; Dijkstra, P. J.; Feijen, J. PEG-PLA hydrogels by stereocomplexation for tissue engineering of cartilage J. Controlled Release 2005, 101 (1-3) 332-334
13. Hiemstra, C.; Zhong, Z. Y.; Jiang, X.; Hennink, W. E.; Dijkstra, P. J.; Feijen, J. PEG-PLLA and PEG-PDLA multiblock copolymers: Synthesis and in situ hydrogel formation by stereocomplexation J. Controlled Release 2006, 116 (2) E17-E19
14. Hiemstra, C.; Zhong, Z. Y.; Li, L. B.; Dijkstra, P. J.; Feijen, J. In-situ formation of biodegradable hydrogels by stereocomplexation of PEG-(PLLA)(8) and PEG-(PDLA)(8) star block copolymers Biomacromolecules 2006, 7 (10) 2790-2795
15. Hiemstra, C.; van der Aa, L. J.; Zhong, Z. Y.; Dijkstra, P. J.; Feijen, J. Rapidly in situ-forming degradable hydrogels from dextran thiols through Michael addition Biomacromolecules 2007, 8 (5) 1548-1556
16. Hiemstra, C.; Zhong, Z.; Van Tomme, S. R.; van Steenbergen, M. J.; Jacobs, J. J. L.; Den Otter, W.; Hennink, W. E.; Feijen, J. In vitro and in vivo protein delivery from in situ forming poly(ethylene glycol)-poly(lactide) hydrogels J. Controlled Release 2007, 119 (3) 320-327
17. Hiemstra, C.; Zhou, W.; Zhong, Z. Y.; Wouters, M.; Feijen, J. Rapidly in situ forming biodegradable robust hydrogels by combining stereocomplexation and photopolymerization J. Am. Chem. Soc. 2007, 129 (32) 9918-9926
18. Ye, S. M.; Lin, T. T.; Tjiu, W. W.; Wong, P. K.; He, C. B. Rubber toughening of poly(lactic acid): Effect of stereocomplex formation at the rubber-matrix interface J. Appl. Polym. Sci. 2013, 128 (4) 2541-2547
19. Tan, B. H.; Hussain, H.; Leong, Y. W.; Lin, T. T.; Tjiu, W. W.; He, C. B. Tuning self-assembly of hybrid PLA-P(MA-POSS) block copolymers in solution via stereocomplexation Polym. Chem. 2013, 4 (4) 1250-1259
20. Sun, Y.; He, C. B. Synthesis, stereocomplex crystallization, morphology and mechanical property of poly(lactide)-carbon nanotube nanocomposites RSC Adv. 2013, 3 (7) 2219-2226
21. Sun, Y.; He, C. B. Synthesis and stereocomplex crystallization of poly(lactide)-graphene oxide nanocomposites ACS Macro Lett. 2012, 1 (6) 709-713
22. Tan, B. H.; Hussain, H.; Lin, T. T.; Chua, Y. C.; Leong, Y. W.; Tjiu, W. W.; Wong, P. K.; He, C. B. Stable dispersions of hybrid nanoparticles induced by stereocomplexation between enantiomeric poly(lactide) star polymers Langmuir 2011, 27 (17) 10538-10547
23. Kali, G.; Georgiou, T. K.; Iván, B.; Patrickios, C. S.; Loizou, E.; Thomann, Y.; Tiller, J. C. Synthesis and characterization of anionic amphiphilic model conetworks based on methacrylic acid and methyl methacrylate: Effects of composition and architecture Macromolecules 2007, 40 (6) 2192-2200
24. Kali, G.; Georgiou, T. K.; Iván, B.; Patrickios, C. S.; Loizou, E.; Thomann, Y.; Tiller, J. C. Synthesis and characterization of anionic amphiphilic model conetworks of 2-butyl-1-octyl-methacrylate and methacrylic acid: Effects of polymer composition and architecture Langmuir 2007, 23 (21) 10746-10755
25. Fodor, C.; Iván, B. Poly(N -vinylimidazole)-l- poly(tetrahydrofuran) amphiphilic conetworks and gels. II. Unexpected dependence of the reactivity of poly(tetrahydrofuran) macromonomer cross-Linker on molecular weight in copolymerization with N -vinylimidazole J. Polym. Sci., Part A: Polym. Chem. 2011, 49 (22) 4729-4734
26. Erdodi, G.; Kennedy, J. P. Amphiphilic conetworks: Definition, synthesis, applications Prog. Polym. Sci. 2006, 31 (1) 1-18
27. Kamata, H.; Chung, U.; Shibayama, M.; Sakai, T. Anomalous volume phase transition in a polymer gel with alternative hydrophilic-amphiphilic sequence Soft Matter 2012, 8 (26) 6876-6879
28. Cui, J.; Lackey, M. A.; Madkour, A. E.; Saffer, E. M.; Griffin, D. M.; Bhatia, S. R.; Crosby, A. J.; Tew, G. N. Synthetically simple, highly resilient hydrogels Biomacromolecules 2012, 13 (3) 584-588
29. Domján, A.; Mezey, P.; Varga, J. Behavior of the interphase region of an amphiphilic polymer conetwork swollen in polar and nonpolar solvent Macromolecules 2012, 45 (2) 1037-1040
30. Domján, A.; Erdodi, G.; Wilhelm, M.; Neidhöfer, M.; Landfester, K.; Iván, B.; Speiss, H. W. Structural studies of nanophase-separated poly(2-hydroxyethyl methacrylate)-l-polyisobutylene amphiphilic conetworks by solid-state NMR and small-angle X-ray scattering Macromolecules 2003, 36 (24) 9107-9114
31. Bruns, N.; Scherble, J.; Hartmann, L.; Thomann, R.; Iván, B.; Mülhaupt, R.; Tiller, J. C. Nanophase separated amphiphilic conetwork coatings and membranes Macromolecules 2005, 38 (6) 2431-2438
32. Tobis, J.; Thomann, Y.; Tiller, J. C. Synthesis and characterization of chiral and thermo responsive amphiphilic conetworks Polymer 2010, 51 (1) 35-45
33. Isayeva, I. S.; Gent, A. N.; Kennedy, J. P. Amphiphilic networks part XVIII-Synthesis and burst strength of water-swollen immunoisolatory tubules J. Polym. Sci., Part A: Polym. Chem. 2002, 40 (12) 2075-2084
34. Haigh, R.; Fullwood, N.; Rimmer, S. Synthesis and properties of amphiphilic networks 2: a differential scanning calorimetric study of poly(dodecyl methacrylate- stat -2,3 propandiol-1-methacrylate-stat-ethandiol dimethacrylate) networks and adhesion and spreading of dermal fibroblasts on these materials Biomaterials 2002, 23 (16) 3509-3516
35. Rimmer, S.; German, M. J.; Maughan, J.; Sun, Y.; Fullwood, N.; Ebdon, J.; MacNeil, S. Synthesis and properties of amphiphilic networks 3: preparation and characterization of block conetworks of poly(butyl methacrylate- block -(2,3 propandiol-1-methacrylate-stat-ethandiol dimethacrylate)) Biomaterials 2005, 26 (15) 2219-2230
36. Kali, G.; Georgiou, T. K.; Iván, B.; Patrickios, C. S. Anionic amphiphilic end-linked conetworks by the combination of quasiliving carbocationic and group transfer polymerizations J. Polym. Sci., Part A: Polym. Chem. 2009, 47 (17) 4289-4301
37. Haraszti, M.; Tóth, E.; Iván, B. Poly(methacrylic acid)-l-polyisobutylene: A novel polyelectrolyte amphiphilic conetwork Chem. Mater. 2006, 18 (20) 4952-4958
38. Lin, C.; Gitsov, I. Preparation and characterization of novel amphiphilic hydrogels with covalently attached drugs and fluorescent markers Macromolecules 2010, 43 (23) 10017-10030
39. Bruns, N.; Tiller, J. C. Amphiphilic network as nanoreactor for enzymes in organic solvents Nano Lett. 2005, 5 (1) 45-48
40. Dech, S.; Cramer, T.; Ladisch, R.; Bruns, N.; Tiller, J. C. Solid-solid interface adsorption of proteins and enzymes in nanophase-separated amphiphilic conetworks Biomacromolecules 2011, 12 (5) 1594-1601
41. Dech, S.; Wruk, V.; Fik, C. P.; Tiller, J. C. Amphiphilic polymer conetworks derived from aqueous solutions for biocatalysis in organic solvents Polymer 2012, 53 (3) 701-707
42. Rimmer, S.; Wilshaw, S. P.; Pickavance, P.; Ingham, E. Cytocompatibility of poly(1,2 propandiol methacrylate) copolymer hydrogels and conetworks with or without alkyl amine functionality Biomaterials 2009, 30 (13) 2468-2478
43. Xu, J. K.; Li, X. S.; Sun, F. Q. In vitro and in vivo evaluation of ketotifen fumarate-loaded silicone hydrogel contact lenses for ocular drug delivery Drug Delivery 2011, 18 (2) 150-158
44. Wang, Y. P.; Finlay, J. A.; Betts, D. E.; Merkel, T. J.; Luft, J. C.; Callow, M. E.; Callow, J. A.; DeSimone, J. M. Amphiphilic co-networks with moisture-induced surface segregation for high-performance nonfouling coatings Langmuir 2011, 27 (17) 10365-10369
45. Aranaz, I.; Carrasco, S.; Tardajos, M. G.; Elvira, C.; Reinecke, H.; Lopez, D.; Gallardo, A. Singular thermosensitivity of polymethyl methacrylate/poly- N -isopropylacrylamide conetworks prepared by a facile synthetic route Polym. Chem. 2011, 2 (3) 709-713
46. Fodor, Cs.; Kali, G.; Iván, B. Poly(N -vinylimidazole)- l -poly(tetrahydrofuran) amphiphilic copetworks and gels: Synthesis, characterization, thermal and swelling behavior Macromolecules 2011, 44 (11) 4496-4502
47. Kali, G.; Vavra, S.; László, K.; Iván, B. Thermally responsive amphiphilic conetworks and gels based on poly(N -isopropylacrylamide) and polyisobutylene Macromolecules 2013, 46 (13) 5337-5344
48. Mespouille, L.; Coulembier, O.; Paneva, D.; Degee, P.; Rashkov, I.; Dubois, P. Novel biodegradable adaptive hydrogels: Controlled synthesis and full characterization of the amphiphilic co-networks Chem.-Eur. J. 2008, 14 (21) 6369-6378
49. Zednik, J.; Riva, R.; Lussis, P.; Jéroîme, C.; Jéroîme, R.; Lecorate, P. pH-responsive biodegradable amphiphilic networks Polymer 2008, 49 (3) 697-702
50. Yuan, Y.; Zhang, A. K.; Ling, J.; Yin, L. H.; Chen, Y.; Fu, G. D. Well-defined biodegradable amphiphilic conetworks Soft Matter 2013, 9 (27) 6309-6318
51. Rikkou, M. D.; Loizou, E.; Porcar, L.; Butler, P.; Patrickios, C. S. Degradable amphiphilic end-linked conetworks with aqueous degradation rates determined by polymer topology Macromolecules 2009, 42 (24) 9412-9421
52. Rikkou-Kalourkoti, M.; Matyjaszewski, K.; Patrickios, C. S. Synthesis, characterization and thermolysis of hyperbranched homo- and amphiphilic co-polymers prepared using an inimer bearing a thermolyzable acylal group Macromolecules 2012, 45 (3) 1313-1320
53. Rikkou-Kalourkoti, M.; Patrickios, C. S. Synthesis and characterization of end-linked amphiphilic copolymer conetworks based on a novel bifunctional cleavable chain transfer agent Macromolecules 2012, 45 (19) 7890-7899
54. Rikkou-Kalourkoti, M.; Loizou, E.; Porcar, L.; Matyjaszewski, K.; Patrickios, C. S. End-linked, amphiphilic, degradable polymer conetworks: Synthesis by sequential atom transfer radical polymerization using a bifunctional, cleavable initiator Polym. Chem. 2012, 3 (1) 105-116
55. Lin, T. T.; Liu, X. Y.; He, C. B. Calculation of infrared/Raman spectra and dielectric properties of various crystalline poly(lactic acid)s by density functional perturbation theory (DFPT) method J. Phys. Chem. B. 2012, 116 (5) 1524-1535
56. Lin, T. T.; Liu, X. Y.; He, C. B. Ab initio elasticity of poly(lactic acid) crystals J. Phys. Chem. B. 2010, 114 (9) 3133-3139
57. Sarasua, J. R.; Prud'homme, R. E.; Wisniewski, M.; Le Borgne, A.; Spassky, N. Crystallization and melting behavior of polylactides Macromolecules 1998, 31 (12) 3895-3905