Skip to main content
Top
Published in: Polymer Bulletin 12/2013

01-12-2013 | Original Paper

Poly(l-lactide) initiated by silver N-heterocyclic carbene complexes: synthesis, characterization and properties

Authors: Sıla Balcan, Mehmet Balcan, Bekir Çetinkaya

Published in: Polymer Bulletin | Issue 12/2013

Log in

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

Abstract

Poly(l-lactide) (PLLA) was successfully synthesized by ring-opening polymerization (ROP) in bulk using silver N-heterocyclic carbene (Ag–NHC) complex. The effect of reaction time, temperature and monomer/initiator ratio on polymerization process were determined. The optimum conditions were found as 130 °C, 4 h and M/I molar ratio of about 100. The polymers were characterized by FTIR, 1H-NMR, GPC and TG. High-molecular-weight PLLA (M w = 3.78 × 104, M n = 1.91 × 104, PDI = 1.97) was synthesized by the ROP of l-lactide (LLA) with bis-(N-methyl N′-dodecylimidazole) silver(I) di-bromo argentate (1a) in bulk. The effect of different N-substituted ligand groups on the polymerization was studied. The antimicrobial activity of the synthesized polymers were investigated by using minimum inhibitory concentration test against gram positive (Staphylococcus aureus) and gram negative (Escherichia coli and Pseudomonas aeruginosa). It was observed that the synthesized polymers displayed moderate antimicrobial activity.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literature
1.
go back to reference Zhang JF, Sun X (2005) Biodegradable polymers for industrial applications. In: Smith R (ed) Poly(lactic acid)-based bioplastics. Woodhead Publishing, Cambridge, pp 251–252 Zhang JF, Sun X (2005) Biodegradable polymers for industrial applications. In: Smith R (ed) Poly(lactic acid)-based bioplastics. Woodhead Publishing, Cambridge, pp 251–252
2.
go back to reference Middleton JC, Tipton AJ (2000) Synthetic biodegradable polymers as orthopedic devices. Biomaterials 21:2335–2346CrossRef Middleton JC, Tipton AJ (2000) Synthetic biodegradable polymers as orthopedic devices. Biomaterials 21:2335–2346CrossRef
3.
go back to reference Ha CS, Gardella JA Jr (2005) Surface chemistry of biodegradable polymers for drug delivery systems. Chem Rev 105:4205–4232CrossRef Ha CS, Gardella JA Jr (2005) Surface chemistry of biodegradable polymers for drug delivery systems. Chem Rev 105:4205–4232CrossRef
4.
go back to reference Wang CH, Fan KR, Hsiue GH (2005) Enzymatic degradation of PLLA–PEOz–PLLA triblock copolymers. Biomaterials 26:2803–2811CrossRef Wang CH, Fan KR, Hsiue GH (2005) Enzymatic degradation of PLLA–PEOz–PLLA triblock copolymers. Biomaterials 26:2803–2811CrossRef
5.
go back to reference Kale G, Auras R, Singh SP, Narayan R (2007) Biodegradability of polylactide bottles in real and simulated composting conditions. Polym Test 26:1049–1061CrossRef Kale G, Auras R, Singh SP, Narayan R (2007) Biodegradability of polylactide bottles in real and simulated composting conditions. Polym Test 26:1049–1061CrossRef
6.
go back to reference Gupta B, Revagade N, Hilborn J (2007) Poly(lactic acid) fiber: an overview. Prog Polym Sci 32:455–482CrossRef Gupta B, Revagade N, Hilborn J (2007) Poly(lactic acid) fiber: an overview. Prog Polym Sci 32:455–482CrossRef
7.
go back to reference Li R, Yao D (2008) Preparation of single poly(lactic acid) composites. J Appl Polym Sci 107:2909–2916CrossRef Li R, Yao D (2008) Preparation of single poly(lactic acid) composites. J Appl Polym Sci 107:2909–2916CrossRef
8.
go back to reference Hyon SH, Jamshidi K, Ikada Y (1997) Synthesis of polylactides with different molecular weights. Biomaterials 18:1503–1508CrossRef Hyon SH, Jamshidi K, Ikada Y (1997) Synthesis of polylactides with different molecular weights. Biomaterials 18:1503–1508CrossRef
9.
go back to reference Drumright RE, Gruber PR, Henton DE (2000) Polylactic acid technology. Adv Mater 12:1841–1846CrossRef Drumright RE, Gruber PR, Henton DE (2000) Polylactic acid technology. Adv Mater 12:1841–1846CrossRef
10.
go back to reference Nijenhuis AJ, Grijpma DW, Pennigs AJ (1992) Lewis acid catalyzed polymerization of l-lactide. Kinetics and mechanism of the bulk polymerization. Macromolecules 25:6419–6424CrossRef Nijenhuis AJ, Grijpma DW, Pennigs AJ (1992) Lewis acid catalyzed polymerization of l-lactide. Kinetics and mechanism of the bulk polymerization. Macromolecules 25:6419–6424CrossRef
11.
go back to reference Albertsson AC, Varma IK (2003) Recent developments in ring opening polymerization of lactones for biomedical applications. Biomacromolecules 4:1466–1486CrossRef Albertsson AC, Varma IK (2003) Recent developments in ring opening polymerization of lactones for biomedical applications. Biomacromolecules 4:1466–1486CrossRef
12.
go back to reference Schwach G, Coudane J, Engel R, Vert M (1997) More about the polymerization of lactides in the presence of stannous octoate. J Polym Sci Part A Polym Chem 35:3431–3440CrossRef Schwach G, Coudane J, Engel R, Vert M (1997) More about the polymerization of lactides in the presence of stannous octoate. J Polym Sci Part A Polym Chem 35:3431–3440CrossRef
13.
go back to reference Korhonen H, Helminen A, Seppala JV (2001) Synthesis of polylactides in the presence of co-initiators with different numbers of hydroxyl groups. Polymer 42:7541–7549CrossRef Korhonen H, Helminen A, Seppala JV (2001) Synthesis of polylactides in the presence of co-initiators with different numbers of hydroxyl groups. Polymer 42:7541–7549CrossRef
14.
go back to reference Kowalski A, Duda A, Penczek S (2000) Kinetics and mechanism of cyclic esters polymerization initiated with tin(II) octoate. Polymerization of l,l-dilactide. Macromolecules 33:7359–7370CrossRef Kowalski A, Duda A, Penczek S (2000) Kinetics and mechanism of cyclic esters polymerization initiated with tin(II) octoate. Polymerization of l,l-dilactide. Macromolecules 33:7359–7370CrossRef
15.
go back to reference Du YJ, Lemstra PJ, Nijenhuis AJ, van Aert HAM, Bastiaansen C (1995) ABA type copolymers of lactide with poly(ethylene glycol). Kinetic, mechanistic and model studies. Macromolecules 28:2124–2132CrossRef Du YJ, Lemstra PJ, Nijenhuis AJ, van Aert HAM, Bastiaansen C (1995) ABA type copolymers of lactide with poly(ethylene glycol). Kinetic, mechanistic and model studies. Macromolecules 28:2124–2132CrossRef
16.
go back to reference Jiang X, Smith MR III, Baker GL (2008) Water-soluble thermoresponsive polylactides. Macromolecules 41:318–324CrossRef Jiang X, Smith MR III, Baker GL (2008) Water-soluble thermoresponsive polylactides. Macromolecules 41:318–324CrossRef
17.
go back to reference Kricheldorf HR, Saunders IK, Stricker A (2000) Polylactones 48. SnOct2-initiated polymerizations of lactide: a mechanistic study. Macromolecules 33:702–709CrossRef Kricheldorf HR, Saunders IK, Stricker A (2000) Polylactones 48. SnOct2-initiated polymerizations of lactide: a mechanistic study. Macromolecules 33:702–709CrossRef
18.
go back to reference Wang C, Li H, Zhao X (2004) Ring opening polymerization of l-lactide initiated by creatinine. Biomaterials 25:5797–5801CrossRef Wang C, Li H, Zhao X (2004) Ring opening polymerization of l-lactide initiated by creatinine. Biomaterials 25:5797–5801CrossRef
19.
go back to reference Samantaray MK, Katiyar V, Roy D, Pang K, Nanavati H, Stephen R, Sunoj RB, Ghosh P (2006) A cationic (N-heterocyclic carbene) silver complex as catalyst for bulk ring-opening polymerization of l-lactides. Eur J Inorg Chem 2006:2975–2984CrossRef Samantaray MK, Katiyar V, Roy D, Pang K, Nanavati H, Stephen R, Sunoj RB, Ghosh P (2006) A cationic (N-heterocyclic carbene) silver complex as catalyst for bulk ring-opening polymerization of l-lactides. Eur J Inorg Chem 2006:2975–2984CrossRef
20.
go back to reference Ray L, Katiyar V, Raihan MJ, Nanavati H, Shaikh MM, Ghosh P (2006) First example of a gold(I) N-heterocyclic-carbene-based initiator for the bulk ring-opening polymerization of l-lactide. Eur J Inorg Chem 2006:3724–3730 CrossRef Ray L, Katiyar V, Raihan MJ, Nanavati H, Shaikh MM, Ghosh P (2006) First example of a gold(I) N-heterocyclic-carbene-based initiator for the bulk ring-opening polymerization of l-lactide. Eur J Inorg Chem 2006:3724–3730 CrossRef
21.
go back to reference Samantaray MK, Katiyar V, Pang K, Nanavati H, Ghosh P (2007) Silver N-heterocyclic carbene complexes as initiators for bulk ring-opening polymerization (ROP) of l-lactides. J Organomet Chem 692:1672–1682CrossRef Samantaray MK, Katiyar V, Pang K, Nanavati H, Ghosh P (2007) Silver N-heterocyclic carbene complexes as initiators for bulk ring-opening polymerization (ROP) of l-lactides. J Organomet Chem 692:1672–1682CrossRef
22.
go back to reference Wang Z, Zhang L, Wang J, Wang Y, Zhang R, Guo X, Liu C (2012) Ring-opening polymerization of 2,2-dimethyltrimethylene carbonate using imidazol-2-ylidenes. Polym Bull 68:141–150CrossRef Wang Z, Zhang L, Wang J, Wang Y, Zhang R, Guo X, Liu C (2012) Ring-opening polymerization of 2,2-dimethyltrimethylene carbonate using imidazol-2-ylidenes. Polym Bull 68:141–150CrossRef
23.
go back to reference Bourissou D, Martin-Vaca BM, Dumitrescu A, Graullier M, Lacombe F (2005) Controlled cationic polymerization of lactide. Macromolecules 38:9993–9998CrossRef Bourissou D, Martin-Vaca BM, Dumitrescu A, Graullier M, Lacombe F (2005) Controlled cationic polymerization of lactide. Macromolecules 38:9993–9998CrossRef
24.
go back to reference Nyce GW, Glauser T, Connor EF, Möck A, Waymouth RM, Hedrick JL (2003) In situ generation of carbenes: a general and versatile platform for organocatalytic living polymerization. J Am Chem Soc 125:3046–3056CrossRef Nyce GW, Glauser T, Connor EF, Möck A, Waymouth RM, Hedrick JL (2003) In situ generation of carbenes: a general and versatile platform for organocatalytic living polymerization. J Am Chem Soc 125:3046–3056CrossRef
25.
go back to reference Culkin DA, Jeong W, Csihony S, Gomez ED, Balsara NP, Hedrick JL, Waymouth RM (2007) Zwitterionic polymerization of lactide to cyclic poly(lactide) by using N-heterocyclic carbene organocatalysts. Angew Chem Int Ed 46:2627–2630CrossRef Culkin DA, Jeong W, Csihony S, Gomez ED, Balsara NP, Hedrick JL, Waymouth RM (2007) Zwitterionic polymerization of lactide to cyclic poly(lactide) by using N-heterocyclic carbene organocatalysts. Angew Chem Int Ed 46:2627–2630CrossRef
26.
go back to reference Pratt RC, Lohmeijer BGG, Long DA, Lundberg PNP, Dove AP, Li H, Wade CG, Waymouth RM, Hedrick JL (2006) Exploration, optimization and application of supramolecular thiourea-amine catalysts for the synthesis of lactide (co)polymers. Macromolecules 39:7863–7871CrossRef Pratt RC, Lohmeijer BGG, Long DA, Lundberg PNP, Dove AP, Li H, Wade CG, Waymouth RM, Hedrick JL (2006) Exploration, optimization and application of supramolecular thiourea-amine catalysts for the synthesis of lactide (co)polymers. Macromolecules 39:7863–7871CrossRef
27.
go back to reference Csihony S, Culkin DA, Sentman AC, Dove AP, Waymouth RM, Hedrick JL (2005) Single-component catalyst/initiators for the organocatalytic ring-opening polymerization of lactide. J Am Chem Soc 127:9079–9084CrossRef Csihony S, Culkin DA, Sentman AC, Dove AP, Waymouth RM, Hedrick JL (2005) Single-component catalyst/initiators for the organocatalytic ring-opening polymerization of lactide. J Am Chem Soc 127:9079–9084CrossRef
28.
go back to reference Sentman AC, Csihony S, Waymouth RM, Hedrick JL (2005) Silver(I)-Carbene Complexes/Ionic Liquids: novel N-heterocyclic carbene delivery agents for organocatalytic transformations. J Org Chem 70:2391–2393CrossRef Sentman AC, Csihony S, Waymouth RM, Hedrick JL (2005) Silver(I)-Carbene Complexes/Ionic Liquids: novel N-heterocyclic carbene delivery agents for organocatalytic transformations. J Org Chem 70:2391–2393CrossRef
29.
go back to reference Garrison JC, Youngs WJ (2005) Ag(I) N-heterocyclic carbene complexes: synthesis, structure and application. Chem Rev 105:3978–4008CrossRef Garrison JC, Youngs WJ (2005) Ag(I) N-heterocyclic carbene complexes: synthesis, structure and application. Chem Rev 105:3978–4008CrossRef
30.
go back to reference Melaiye A, Sun Z, Hindi K, Milsted A, Ely D, Reneker DH, Tessier CA, Youngs WJ (2005) Silver(I)-imidazole cyclophane gem-diol complexes encapsulated by electrospun tecophilic nanofibers: formation of nanosilver particles and antimicrobial activity. J Am Chem Soc 127:2285–2291CrossRef Melaiye A, Sun Z, Hindi K, Milsted A, Ely D, Reneker DH, Tessier CA, Youngs WJ (2005) Silver(I)-imidazole cyclophane gem-diol complexes encapsulated by electrospun tecophilic nanofibers: formation of nanosilver particles and antimicrobial activity. J Am Chem Soc 127:2285–2291CrossRef
31.
go back to reference Siciliano TJ, Deblock MC, Hindi KM, Durmus S, Panzner MJ, Tessier CA, Youngs WJ (2011) Synthesis and anticancer properties of gold(I) and silver(I) N-heterocyclic carbene complexes. J Organomet Chem 696:1066–1071CrossRef Siciliano TJ, Deblock MC, Hindi KM, Durmus S, Panzner MJ, Tessier CA, Youngs WJ (2011) Synthesis and anticancer properties of gold(I) and silver(I) N-heterocyclic carbene complexes. J Organomet Chem 696:1066–1071CrossRef
32.
go back to reference Melaiye A, Simons RS, Milsted A, Pingitore F, Wesdemiotis C, Tessier CA, Youngs WJ (2004) Formation of water-soluble pincer silver(I)-carbene complexes: a novel antimicrobial agent. J Med Chem 47:973–977CrossRef Melaiye A, Simons RS, Milsted A, Pingitore F, Wesdemiotis C, Tessier CA, Youngs WJ (2004) Formation of water-soluble pincer silver(I)-carbene complexes: a novel antimicrobial agent. J Med Chem 47:973–977CrossRef
33.
go back to reference Tasçı Z, Kunduracioglu A, Kani I, Çetinkaya B (2012) A new application area for Ag–NHCs: CO2 fixation catalyst. Chem Cat Chem 4:831–835 Tasçı Z, Kunduracioglu A, Kani I, Çetinkaya B (2012) A new application area for Ag–NHCs: CO2 fixation catalyst. Chem Cat Chem 4:831–835
34.
go back to reference Clinical and Laboratory Standards Institute (CLSI) (2005) Performance standards for antimicrobial susceptibility testing: 15th Informational Supplement. CLSI Document M100-S15. Wayne, PA, USA Clinical and Laboratory Standards Institute (CLSI) (2005) Performance standards for antimicrobial susceptibility testing: 15th Informational Supplement. CLSI Document M100-S15. Wayne, PA, USA
35.
go back to reference Stephen R, Sunoj RB, Ghosh P (2011) A computational insight into a metal mediated pathway for the ring-opening polymerization (ROP) of lactides by an ionic {(NHC)2Ag}+X− (X = halide) type N-heterocyclic carbene (NHC) complex. Dalton Trans 40:10156–10161CrossRef Stephen R, Sunoj RB, Ghosh P (2011) A computational insight into a metal mediated pathway for the ring-opening polymerization (ROP) of lactides by an ionic {(NHC)2Ag}+X (X = halide) type N-heterocyclic carbene (NHC) complex. Dalton Trans 40:10156–10161CrossRef
36.
go back to reference Odian G (2004) Principles of polymerization. In: Ring opening polymerization, 4rd edn. Wiley, New Jersey, pp 546–547 Odian G (2004) Principles of polymerization. In: Ring opening polymerization, 4rd edn. Wiley, New Jersey, pp 546–547
37.
go back to reference Yuan M, Liu D, Xiong C, Deng X (1999) Polymerization of lactides and lactones 6. Synthesis of polyDL-lactide and polyethylene glycol-co-polydl-lactide copolymer with allylmagnesium chloride. Eur Polymer J 35:2139–2145CrossRef Yuan M, Liu D, Xiong C, Deng X (1999) Polymerization of lactides and lactones 6. Synthesis of polyDL-lactide and polyethylene glycol-co-polydl-lactide copolymer with allylmagnesium chloride. Eur Polymer J 35:2139–2145CrossRef
38.
go back to reference Wang X, Liao K, Quan D, Wu Q (2005) Bulk ring-opening polymerization of lactides initiated by ferric alkoxides. Macromolecules 38:4611–4617CrossRef Wang X, Liao K, Quan D, Wu Q (2005) Bulk ring-opening polymerization of lactides initiated by ferric alkoxides. Macromolecules 38:4611–4617CrossRef
Metadata
Title
Poly(l-lactide) initiated by silver N-heterocyclic carbene complexes: synthesis, characterization and properties
Authors
Sıla Balcan
Mehmet Balcan
Bekir Çetinkaya
Publication date
01-12-2013
Publisher
Springer Berlin Heidelberg
Published in
Polymer Bulletin / Issue 12/2013
Print ISSN: 0170-0839
Electronic ISSN: 1436-2449
DOI
https://doi.org/10.1007/s00289-013-1034-9

Other articles of this Issue 12/2013

Polymer Bulletin 12/2013 Go to the issue

Premium Partners