Synthesis, characterization, and hydrolytic degradation of graft copolymers of polystyrene and aliphatic polyesters

Designed Monomers and Polymers

Volumn 16, Issue 3, 2013, Pages 233-240

  Kukut, Manolya ^a   Karal Yilmaz, Oksan ^b   Yagci, Yusuf ^a,c  

^a ISTANBUL TECHNICAL UNIVERSITY   (Turkey)

^b MATERIALS INSTITUTE   (Turkey)

^c KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

Click chemistry; Hydrolytic degradation; Poly(L lactic acid); Poly(L lactic co glycolic acid)

Indexed keywords

CLICK CHEMISTRY; FOURIER TRANSFORM INFRA REDS; HYDROLYTIC DEGRADATION; NITROXIDE-MEDIATED FREE RADICAL POLYMERIZATIONS; PHOSPHATE BUFFER SALINES; POLY (L-LACTIC-CO-GLYCOLIC ACID); POLY L LACTIC ACID; PROTON NUCLEAR MAGNETIC RESONANCE;

FREE RADICAL POLYMERIZATION; GEL PERMEATION CHROMATOGRAPHY; IODINE; LACTIC ACID; POLYPROPYLENES; POLYSTYRENES; STYRENE; SYNTHESIS (CHEMICAL);

GRAFT COPOLYMERS;

EID: 84878058406     PISSN: 1385772X     EISSN: 15685551     Source Type: Journal    
DOI: 10.1080/15685551.2012.725214     Document Type: Article

References (53)

1. Edlund U, Albertsson AC. Degradable polymer microspheres for controlled drug delivery. Advances in Polymer Science. 2002;157:67-112.
2. Moravek SJ, Storey RF. Copolymers of rac-lactide and ε-caprolactone: conventional copolymerization vs. macroinitiator copolymerization. Journal of Macromolecular Science, Pure Applied Chemistry. 2009;46:339-345.
3. Lue J-M, Wang X, Marin-Muller C, Wang H, Lin PH, Yao Q, Chen C. Current advances in research and clinical applications of PLGA-based nanotechnology. Expert Review of Molecular Diagnostics. 2009;9:325-341.
4. Gupta AP, Kumar V. Synthesis and characterization of novel chain-linked biodegradable polymers. Designed Monomers and Polymers. 2010;13:65-72.
5. Zhou ZH, Liu XP, Lin LH. Preparation and biocompatibility of poly(L-lactide-co-glycolide) scaffold materials for nerve conduits. Designed Monomers and Polymers. 2008;11:447-456.
6. Carrot G, Hilborn JG, Trollsas M, Hedrick JL. Two general methods for the synthesis of thiol-functional polycaprolactones. Macromolecules. 1999;32:5264-5269.
7. Ouchi T, Seike H, Miyazaki H, Tasaka F, Ohya Y. Synthesis of a block copolymer of L-lactide and depsipeptide with pendant thiol groups. Designed Monomers and Polymers. 2000;3:279-287. (Pubitemid 32478194)
8. Lu FZ, Xiong XY, Li ZC, Du FS, Zhang BY, Li FM. A convenient method for the synthesis of amine-terminated poly(ethylene oxide) and poly(epsilon- caprolactone). Bioconjugate Chemistry. 2002;13:1159-1162.
9. Cometa S, Bartolozzi I, Corti A, Chiellini F, De Giglio E, Chiellini E. Hydrolytic and microbial degradation of multi-block polyurethanes based on poly(ε-caprolactone)/poly(ethylene glycol) segments. Polymer Degradation and Stability. 2010;95:2013-2021.
10. Corti A, Muniyasamy S, Vitali M, Imam SH, Chiellini E. Oxidation and biodegradation of polyethylene films containing pro-oxidant additives: synergistic effects of sunlight exposure, thermal aging and fungal biodegradation. Polymer Degradation and Stability. 2010;95:1106-1114.
11. Cordova A, Iversen T, Hult K. Lipase-catalyzed formation of end-functionalized poly(ε-caprolactone) by initiation and termination reactions. Polymer. 1999;40:6709-6721. (Pubitemid 29404810)
12. Kayaman-Apohan N, Karal-Yilmaz O, Baysal K, Baysal BM. Polymer. 2001;42:4109.
13. Porjazoska A, Kayaman-Apohan N, Karal-Yilmaz O, Cvetkovska M, Baysal K, Baysal BM. Synthesis and characterization of glycolide, L-lactide and PDMS based terpolymers as a support for cell cultures. Journal of Biomaterials Science Polymer Edition. 2002;13: 1119-1134. (Pubitemid 35402148)
14. Porjazoska A, Karal-Yilmaz O, Kayaman-Apohan N, Cvetkovska M, Baysal BM. Biocompatible polymer blends of poly(D, L-lactic acid-co-glycolic acid) and triblock PCL-PDMS-PCL copolymers: their characterizations and degradations. Zagreb: Croatian Chemical Society; 2004. p. 545-551.
15. Nampoothiri KM, Nair NR, John RP. An overview of the recent developments in polylactide (PLA) research. Bioresource Technology. 2010;101:8493-8501.
16. Wiggins JS, Hassan MK, Mauritz KA, Storey RF. Hydrolytic degradation of poly(D,L-Lactide) as a function of end group: carboxylic acid vs. hydroxyl. Polymer. 2006;47:1960-1969. (Pubitemid 43344370)
17. Moravek SJ, Messman JM, Storey RF. Copolymers of raclactide and ε-caprolactone: conventional copolymerization vs. macroinitiator copolymerization. Journal of Polymer Science Part A: Polymer Chemistry. 2009;47:797-803.
18. Detta N, El-Fattah AA, Chiellini E, Walkenstrom P, Gatenholm P. Biodegradable polymeric micro-nanofibres by electrospinning of polyester/polyether block copolymers. Journal of Applied Polymer Science. 2008;110:253-261.
19. Cometa S, Chiellini F, Bartolozzi I, Chiellini E, De Giglio E, Sabbatini L. Surface segregation assessment in poly(3- caprolactone)-poly(ethylene glycol) multi-block copolymer films. Macromolecular Bioscience. 2010;10:317-327.
20. Tasdelen MA. Poly(epsilon-caprolactone)/clay nanocomposites via 'click' chemistry. European Polymer Journal. 2011;47:937-941.
21. Colak DG, Cianga I, Yagci Y, Cirpan A, Karasz FE. Novel poly(phenylene vinylenes) with well-defined poly (epsilon-caprolactone) or polystyrene as lateral substituents: synthesis and characterization. Macromolecules. 2007;40:5301-5310. (Pubitemid 47210154)
22. Kiskan B, Yagci Y. Synthesis and characterization of naphthoxazine functional poly(ε-caprolactone). Polymer. 2005;46:11690-11697. (Pubitemid 41653364)
23. Yurteri S, Cianga I, Demirel AL, Yagci Y. New polyphenylene-g-polystyrene and polyphenylene-g-polystyrene/poly (ε-caprolactone) copolymers by combined controlled polymerization and cross-coupling processes. Journal of Polymer Science Part A: Polymer Chemistry. 2005;43:879-896. (Pubitemid 40206682)
24. Yurteri S, Cianga I, Degirmenci M, Yagci Y. Synthesis and characterization of poly(p-phenylene)-graft-poly (ε-caprolactone) copolymers by combined ring-opening polymerization and cross-coupling processes. Polymer International. 2004;53:1219-1225. (Pubitemid 39112671)
25. Nur Y, Yurteri S, Cianga I, Yagci Y, Hacaloglu J. Thermal degradation of poly(p-phenylene-graft-ε-caprolactone) copolymer. Polymer Degradation Stability. 2007;92:838-848.
26. Muftuoglu AE, Cianga M, Colak D, Yagci Y. Synthesis, characterization and electrochromic properties of a conducting copolymer of pyrrole functionalized polystyrene with pyrrole. Designed Monomers Polymers. 2004;7:563-582.
27. Tasdelen MA, Beyazit S, Gunes D, Bicak N, Tatar P, Demirel AL, Yagci Y. Poly(p-phenylene methylene)-based block copolymers by mechanistic transformation. Journal of Polymer Science Part B: Polymer Chemistry. 2011;49:4021-4026.
28. Degirmenci M, Hizal G, Yagci Y. Synthesis and characterization of macrophotoinitiators of poly(ε-caprolactone) and their use in block copolymerization. Macromolecules. 2002;35:8265-8270. (Pubitemid 35263705)
29. Degirmenci M, Izgin O, Yagci Y. Synthesis and characterization of cyclohexene oxide functional poly (epsilon-caprolactone) macromonomers and their use in photoinitiated cationic homo- and copolymerization. Journal of Polymer Science Part A: Polymer Chemistry. 2004;42:3365-3372.
30. Kerman I, Toppare L, Yilmaz F, Yagci Y. Thiophene ended epsilon-caprolactone conducting copolymers and their electrochromic properties. Journal of Macromolecular Science, Pure and Applied Chemistry. 2005;A42:509-520. (Pubitemid 40540395)
31. Tasdelen MA, Kahveci MU, Yagci Y. Telechelic polymers by living and controlled/living polymerization methods. Progress in Polymer Science. 2011;36:455-567.
32. Kolb HC, Finn MG, Sharpless KB. Click chemistry: diverse chemical function from a few good reactions. Angewandte Chemie International Edition. 2001;40:2004-2021.
33. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective 'ligation' of azides and terminal alkynes. Angewandte Chemie International Edition. 2002;41:2596-2599. (Pubitemid 34803480)
34. Tornoe CW, Christensen C, Meldal M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. Journal of Organic Chemistry. 2002;67:3057-3064. (Pubitemid 34457265)
35. Iskin B, Yilmaz G, Yagci Y. ABC type miktoarm star copolymers through combination of controlled polymerization techniques with thiol-ene and azide-alkyne click reactions. Journal of Polymer Science Part A: Polymer Chemistry. 2011;49:2417-2422.
36. Iskin B, Yilmaz G, Yagci Y. Synthesis of ABC type miktoarm star copolymers by triple click chemistry. Polymer Chemistry. 2011;2:2865-2871.
37. Tasdelen MA, Yilmaz G, Iskin B, Yagci Y. Photoinduced free radical promoted copper(I)-catalyzed click chemistry for macromolecular syntheses. Macromolecules. 2012;45:56-61.
38. Cengiz H, Aydogan B, Ates S, Acikalin E, Yagci Y. Intramolecular cross-linking of polymers by using difunctional acetylenes via click chemistry. Designed Monomers and Polymer. 2011;14:69-78.
39. Yilmaz G, Toiserkani H, Demirkol DO, Sakarya S, Timur S, Orun L, Orun L. Polysulfone based amphiphilic graft copolymers by click chemistry as bioinert membranes. Materials Science and Engineering: C. 2011;31:1091-1097.
40. Gacal BN, Koz B, Gacal B, Kiskan B, Erdogan M, Yagci Y. Pyrene functional poly(vinyl alcohol) by 'click' chemistry. Journal of Polymer Science Part A: Polymer Chemistry. 2009;47:1317-1326.
41. Kukut M, Kiskan B, Yagci Y. Self-curable benzoxazine functional polybutadienes synthesized by click chemistry. Designed Monomers and Polymers. 2009;12:167-176.
42. Toiserkani H, Yilmaz G, Yagci Y, Torun L. Functionalization of polysulfones by click chemistry. Macromolecular Chemistry and Physics. 2010;211:2389-2395.
43. Durmaz YY, Sangermano M, Yagci Y. Surface modification of UV-cured epoxy resins by click chemistry. Journal of Polymer Science Part A: Polymer Chemistry. 2010;48:2862-2868.
44. Okcu SS, Durmaz YY, Yagci Y. Synthesis and characterization of telechelic block co-polymers by combination of atom transfer radical polymerization and click chemistry processes. Designed Monomers and Polymers. 2010;13:459-472.
45. Yilmaz G, Toiserkani H, Demirkol DO, Sakarya S, Timur S, Yagci Y, Torun L. Modification of polysulfones by click chemistry: amphiphilic graft copolymers and their protein adsorption and cell adhesion properties. Journal of Polymer Science Part A: Polymer Chemistry. 2011;49:110-117.
46. Ates S, Durmaz YY, Torun L, Yagci Y. Synthesis and characterization of polystyrene possessing triptycene units in the main chain by combination of ATRP and click chemistry processes. Journal of Macromolecular Science: Pure and Applied Chemistry. 2010;47:809-815.
47. Tasdelen MA, Yagci Y. Light-induced copper(I)-catalyzed click chemistry. Tetrahedron Letters. 2010;51:6945-6947.
48. Karagoz B, Durmaz YY, Gacal BN, Bicak N, Yagci Y. Functionalization of poly(divinylbenzene) microspheres by combination of hydrobromination and click chemistry processes: a model study. Designed Monomers and Polymers. 2009;12:511-522.
49. Tasdelen MA, Van Camp W, Goethals E, Dubois P, Du Prez F, Yagci Y. Polytetrahydrofuran/clay nanocomposites by in situ polymerization and 'click' chemistry processes. Macromolecules. 2008;41:6035-6040.
50. Oral A, Tasdelen MA, Demirel AL, Yagci Y. Poly(methyl methacrylate)/clay nanocomposites by photoinitiated free radical polymerization using intercalated monomer. Polymer. 2009;50:3905-3910.
51. Ak M, Gacal B, Kiskan B, Yagci Y, Toppare L. Enhancing electrochromic properties of polypyrrole by silsesquioxane nanocages. Polymer. 2008;49:2202-2210.
52. Gacal B, Durmaz H, Tasdelen MA, Hizal G, Tunca U, Yagci Y, Demirel AL. Anthracene-maleimide-based Diels-Alder 'click chemistry' as a novel route to graft copolymers. Macromolecules. 2006;39:5330-5336. (Pubitemid 44325110)
53. Li J, Li H, Wu C, Ke Y, Wang D, Li Q, Zhang L, Hu Y. Morphologies, crystallinity and dynamic mechanical characterizations of polypropylene/ polystyrene blends compatibilized with PP-g-PS copolymer: effect of the side chain length. European Polymer Journal. 2009;45:2619-2628.