989
Views
6
CrossRef citations to date
0
Altmetric
Articles

Synthesis of mid-chain functional macrophotoinitiators of poly(D,L-lactide) homopolymer and tetrablock poly(D,L-lactide)-poly(ε-caprolactone) copolymer by ring-opening polymerization

, , &
Pages 669-677 | Received 13 Feb 2015, Accepted 21 Jun 2015, Published online: 30 Jul 2015

References

  • Lendlein A, Sisson A. Handbook of biodegradable polymers. Weinheim: Wiley-VCH Verlag GmbH & Co.; 2011.10.1002/9783527635818
  • Albertsson AC, Varma IK. Recent developments in ring opening polymerization of lactones for biomedical applications. Biomacromolecules. 2003;4:1466–1486.10.1021/bm034247a
  • Pilla S. Handbook of bioplastics and biocomposites engineering applications. Weinheim: Wiley-VCH Verlag GmbH & Co.; 2011.10.1002/9781118203699
  • Kowalski A, Duda A, Penczek S. Polymerization of L,L-lactide initiated by aluminum isopropoxide trimer or tetramer. Macromolecules. 1998;31:2114–2122.10.1021/ma971737k
  • Bouyahyi M, Duchateau R. Metal-based catalysts for controlled ring-opening polymerization of macrolactones: high molecular weight and well-defined copolymer architectures. Macromolecules. 2014;47:517–524.10.1021/ma402072t
  • Contreras J, Pestana J, López-Carrasquero F, Torres C. Synthesis of ε-caprolactone-b-L-lactide block copolymers by mean sequential polymerization, using diphenylzinc as initiator. Polym. Bull. 2014;71:1661–1674.10.1007/s00289-014-1147-9
  • Contreras J, Dávila D. Ring-opening copolymerization of L-lactide with ɛ-caprolactone initiated by diphenylzinc. Polym. Int. 2006;55:1049–1056.10.1002/(ISSN)1097-0126
  • Chuang HJ, Chen HL, Huang BH, et al. Efficient zinc initiators supported by NNO-tridentate ketiminate ligands for cyclic esters polymerization. J. Polym. Sci. Part A: Polym. Chem. 2013;51:1185–1196.10.1002/pola.26486
  • Dechy-Cabaret O, Martin-Vaca B, Bourissou D. Controlled ring-opening polymerization of lactide and glycolide. Chem. Rev. 2004;104:6147–6176.10.1021/cr040002s
  • Gardella L, Cavallo D, Colonna S, Fina A, Monticelli O. Novel poly(L-lactide)/poly(D-lactide)/poly(tetrahydrofuran) multiblock copolymers with a controlled architecture: synthesis and characterization. J. Polym. Sci. Part A: Polym. Chem. 2014;52:3269–3282.10.1002/pola.v52.22
  • Labet M, Thielemans W. Synthesis of polycaprolactone: a review. Chem. Soc. Rev. 2009;38:3484–3504.10.1039/b820162p
  • Kricheldorf HR, Kreiser-Saunders I, Stricker A. Polylactones 48. SnOct2-initiated polymerizations of lactide: a mechanistic study. Macromolecules. 2000;33:702–709.10.1021/ma991181w
  • Degirmenci M, Hizal G, Yagci Y. Synthesis and characterization of macrophotoinitiators of poly(ε-caprolactone) and their use in block copolymerization. Macromolecules. 2002;35:8265–8270.10.1021/ma020668t
  • Martello MT, Schneiderman DK, Hillmyer MA. Synthesis and melt processing of sustainable poly(ε-decalactone)-block-poly(lactide) multiblock thermoplastic elastomers. ACS Sustainable Chem. Eng. 2014;2:2519–2526.10.1021/sc500412a
  • Biela T, Kowalski A, Libiszowski J, Duda A, Penczek S. Progress in polymerization of cyclic esters: mechanisms and synthetic applications. Macromol. Symp. 2006;240:47–55.10.1002/(ISSN)1521-3900
  • In’t Veld PJA, Velner EM, Van de Witte P, Hamhuis J, Dijkstra PJ, Feijen J. Melt block copolymerization of ε-caprolactone and L-lactide. J. Polym. Sci. Part A: Polym. Chem. 1997;35:219–226.
  • Kim JK, Park DJ, Lee MS, Ihn KJ. Synthesis and crystallization behavior of poly(L-lactide)-block-poly(ε-caprolactone) copolymer. Polymer. 2001;42:7429–7441.10.1016/S0032-3861(01)00217-8
  • Pensec S, Leroy M, Akkouche H, Spassky N. Stereocomplex formation in enantiomeric diblock and triblock copolymers of poly (ε-caprolactone) and polylactide. Polym. Bull. 2000;45:373–380.10.1007/s002890070010
  • Qian H, Bei J, Wang S. Synthesis, characterization and degradation of ABA block copolymer of L-lactide and ε-caprolactone. Polym. Degrad. Stab. 2000;68:423–429.10.1016/S0141-3910(00)00031-8
  • Maglio G, Migliozzi A, Palumbo R. Thermal properties of di- and triblock copolymers of poly(L-lactide) with poly(oxyethylene) or poly(ε-caprolactone). Polymer. 2003;44:369–375.10.1016/S0032-3861(02)00764-4
  • Tamboli V, Mishra GP, Mitra AK. Novel pentablock copolymer (PLA–PCL–PEG–PCL–PLA)-based nanoparticles for controlled drug delivery: effect of copolymer compositions on the crystallinity of copolymers and in vitro drug release profile from nanoparticles. Colloid Polym. Sci. 2013;291:1235–1245.10.1007/s00396-012-2854-0
  • Yağci Y Macrophotoinitiators: synthesis and their use in block copolymerization. In: Mishra MK, Nuyken O, Kobayashi S, Yağci Y, Sar B, editors. Macromolecular engineering.New York (NY): Plenium Press; 1995. Chapter 11, p. 151–161.10.1007/978-1-4615-1905-8
  • Corrales T, Catalina F, Peinado C, Allen NS. Free radical macrophotoinitiators: an overview on recent advances. J. Photochem. Photobiol. A. 2003;159:103–114.10.1016/S1010-6030(03)00175-8
  • Carlini C, Angiolini L, Caretti D, Corelli E. Recent advances on photosensitive polymers: polymeric photoinitiators. Polym. Adv. Technol. 1996;7:379–384.10.1002/(ISSN)1099-1581
  • Fouassier J. Photoinitiation, photopolymerisation and photocuring: fundamentals and applications. Munich: Hanser; 1995.
  • Allen NS, editor. Photopolymerisation and photoimaging science and technology. Oxford: Elsevier; 1989.
  • Jiang XS, Luo XW, Yin J. Polymeric photoinitiators containing in-chain benzophenone and coinitiators amine: effect of the structure of coinitiator amine on photopolymerization. J. Photochem. Photobiol. A. 2005;174:165–170.10.1016/j.jphotochem.2005.02.008
  • Wang Y, Jiang X, Yin J. Novel polymeric photoinitiators comprising of side-chain benzophenone and coinitiator amine: photochemical and photopolymerization behaviors. Eur. Polym. J. 2009;45:437–447.10.1016/j.eurpolymj.2008.10.039
  • Davidson RS. Polymeric and polymerisable free radical photoinitiators. J. Photochem. Photobiol. A. 1993;69:263–275.10.1016/1010-6030(93)85092-M
  • Degirmenci M, Sarac MA, Genli N. Synthesis and characterization of mid-chain macrophotoinitiator of poly(ε-caprolactone) by combination of ROP and click chemistry. Polym. Bull. 2014;71:1743–1755.10.1007/s00289-014-1152-z
  • Ohar H, Dolynska L, Tokarev V. Synthesis and application of macrophotoinitiators obtained via benzoin tethering with copolymers of maleic anhydride. Chem. Chem. Technol. 2013;7:125–130.
  • Degirmenci M, Cianga I, Hizal G, Yagci Y. Synthesis, characterization and application of polymeric photoinitiators prepared by atom transfer radical polymerization and ring-opening polymerization. Polym. Prepr. 2002;43:22–23.
  • Degirmenci M, Genli N. Synthesis of well-defined telechelic macrophotoinitiator of polystyrene by combination of ATRP and click chemistry. Macromol. Chem. Phys. 2009;210:1617–1623.10.1002/macp.v210:19
  • Temel G, Arsu N. One-pot synthesis of water-soluble polymeric photoinitiator via thioxanthonation and sulfonation process. J. Photochem. Photobiol. A. 2009;202:63–66.10.1016/j.jphotochem.2008.11.012
  • Durmaz YY, Yilmaz G, Yağci Y N-alkoxy pyridinium ion terminated polystyrenes: a facile route to photoinduced block copolymerization. J. Polym. Sci. Part A: Polym. Chem. 2007;45:423–428.10.1002/(ISSN)1099-0518
  • Degirmenci M, Cianga I, Yagci Y. Synthesis of well-defined polystyrene macrophotoinitiators by atom-transfer radical polymerization. Macromol. Chem. Phys. 2002;203:1279–1284.10.1002/1521-3935(200207)203:10/11<1279::AID-MACP1279>3.0.CO;2-H
  • Degirmenci M, Alter S, Genli N. Synthesis and characterization of well-defined mid-chain functional macrophotoinitiators of polystyrene by combination of ATRP and “click” chemistry. Macromol. Chem. Phys. 2011;212:1575–1581.10.1002/macp.v212.15
  • Degirmenci M Synthesis and characterization of novel well‐defined end‐functional macrophotoinitiator of poly(MMA) by ATRP J. Macromol. Sci. Part A-Pure Appl. Chem. 2005;42:21–30.10.1081/MA-200040949
  • Degirmenci M. Synthesis of novel well-defined end-functional macrophotoinitiator of poly(ε-caprolactone) by ring-opening polymerization. Polym. J. 2004;36:542–548.10.1295/polymj.36.542
  • Degirmenci M, Besli PA, Genli N. Synthesis of a well-defined end-chain macrophotoinitiator of poly(ε-caprolactone) by combination of ring-opening polymerization and click chemistry. J. Polym. Res. 2014;21:540–549.10.1007/s10965-014-0540-2
  • Save M, Schappacher M, Soum A. Controlled ring-opening polymerization of lactones and lactides initiated by lanthanum isopropoxide, 1. General aspects and kinetics. Macromol. Chem. Phys. 2002;203:889–899.10.1002/1521-3935(20020401)203:5/6<889::AID-MACP889>3.0.CO;2-O
  • César-Oliveira MAF, Zaioncz S, Oliveira ARS, et al. Síntese de copolímeros metacrílicos através da modificação química do poli(metacrilato de metila) de massa molar controlada [Synthesis of methacrylic copolymers by chemical modification of poly(methyl methacrylate) with controlled molecular weight]. Polímeros. 1999;9:156–162.10.1590/S0104-14281999000400026
  • Vangani V, Rakshit AK. Synthesis and characterization of homopolymer of 2-ethylhexyl acrylate and its copolymers with acrylamide, acrylonitrile, and methyl methacrylate. J. Appl. Polym. Sci. 1996;60:1005–1013.10.1002/(ISSN)1097-4628
  • Gong S, Ma H, Wan X. Atom transfer radical polymerization of methyl methacrylate induced by an initiator derived from an ionic liquid. Polym. Int. 2006;55:1420–1425.10.1002/(ISSN)1097-0126

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.