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Original Articles

L-menthol-based xanthate mediator for RAFT polymerization of vinyl acetate

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Pages 299-309 | Received 20 Sep 2019, Accepted 18 Oct 2019, Published online: 23 Nov 2019

References

  • Hassan, C. M.; Peppas, N. A. Structure and Applications of Poly(Vinyl Alcohol) Hydrogels Produced by Conventional Crosslinking or by Freezing/Thawing Methods. Adv. Polym. Sci. 2000, 153, 37–65. DOI: 10.1007/3-540-46414-X_2.
  • Lee, K. Y.; Mooney, D. J. Hydrogels for Tissue Engineering. Chem. Rev. 2001, 101, 1869–1880. DOI: 10.1021/cr000108x.
  • Uhrich, K. E.; Cannizzaro, S. M.; Langer, R. S.; Shakesheff, K. M. Polymeric Systems for Controlled Drug Release. Chem. Rev. 1999, 99, 3181–3198. DOI: 10.1021/cr940351u.
  • Greszta, D.; Mardare, D.; Matyjaszewski, K. Living” Radical Polymerization. 1. Possibilities and Limitations. Macromolecules 1994, 27, 638–644. DOI: 10.1021/cr940351u.
  • Iovu, M. C.; Matyjaszewski, K. Controlled/Living Radical Polymerization of Vinyl Acetate by Degenerative Transfer with Alkyl Iodides. Macromolecules 2003, 36, 9346–9354. DOI: 10.1021/ma034892+.
  • Charmot, D.; Corpart, P.; Adam, H.; Zard, S. Z.; Biadatti, T.; Bouhadir, G. Controlled Radical Polymerization in Dispersed Media. Macromol. Symp. 2000, 150, 23–32. DOI: 10.1002/1521-3900(200002)150:1 < 23::AID-MASY23 > 3.0.CO;2-E.
  • Stenzel, M. H.; Cummins, L.; Roberts, G. E.; Davis, T. R.; Vana, P.; Barner-Kowollik, C. Xanthate Mediated Living Polymerization of Vinyl Acetate: A Systematic Variation in MADIX/RAFT Agent Structure. Macromol. Chem. Phys. 2003, 204, 1160–1168. DOI: 10.1021/ma034892+.
  • Coote, M.; Radom, L. Substituent Effects in Xanthate-Mediated Polymerization of Vinyl Acetate: Ab Initio Evidence for an Alternative Fragmentation Pathway. Macromolecules 2004, 37, 590–596. DOI: 10.1021/ma035477k.
  • Favier, A.; Barner-Kowollik, C.; Davis, T. P.; Stenzel, M. H. A Detailed on‐Line FT/NIR and 1H NMR Spectroscopic Investigation into Factors Causing Inhibition in Xanthate‐Mediated Vinyl Acetate Polymerization. Macromol. Chem. Phys. 2004, 205, 925–936. DOI: 10.1002/macp.200300179.
  • Simms, R. W.; Davis, T. P.; Cunningham, M. F. Xanthate‐Mediated Living Radical Polymerization of Vinyl Acetate in Miniemulsion. Macromol. Rapid Commun. 2005, 26, 592–596. DOI: 10.1002/marc.200400652.
  • Bernard, J.; Favier, A.; Zhang, L.; Nilasaroya, A.; Davis, T. P.; Barner-Kowollik, C.; Stenzel, M. H. Poly(Vinyl Ester) Star Polymers via Xanthate-Mediated Living Radical Polymerization: From Poly(Vinyl Alcohol) to Glycopolymer Stars. Macromolecules 2005, 38, 5475–5484. DOI: 10.1021/ma050050u.
  • Bernard, J.; Favier, A.; Davis, T. P.; Barner-Kowollik, C.; Stenzel, M. H. Synthesis of Poly(Vinyl Alcohol) Combs via MADIX/RAFT Polymerization. Polymer 2006, 47, 1073–1080. DOI: 10.1016/j.polymer.2005.12.004.
  • Pound, G.; Aguesse, F.; McLeary, J. B.; Lange, R. F. M.; Klumperman, B. Xanthate-Mediated Copolymerization of Vinyl Monomers for Amphiphilic and Double-Hydrophilic Block Copolymers with Poly(Ethylene Glycol). Macromolecules 2007, 40, 8861–8871. DOI: 10.1021/ma0710075.
  • Tong, Y.-Y.; Dong, Y.-Q.; Du, F.-S.; Li, Z.-C. Synthesis of Well-Defined Poly(Vinyl Acetate)-b-Polystyrene by Combination of ATRP and RAFT Polymerization. Macromolecules 2008, 41, 7339–7346. DOI: 10.1021/ma800799x.
  • Lipscomb, C. E.; Mahanthappa, M. K. Poly(Vinyl Ester) Block Copolymers Synthesized by Reversible Addition − Fragmentation Chain Transfer Polymerizations. Macromolecules 2009, 42, 4571–4579. DOI: 10.1021/ma900477d.
  • Bernard, J.; Lortie, F.; Bernard, F. Design of Heterocomplementary H‐Bonding RAFT Agents – towards the Generation of Supramolecular Star Polymers. Macromol. Rapid Commun. 2009, 30, 83–88. DOI: 10.1002/marc.200800586.
  • Chen, S.; Bertrand, A.; Chang, X.; Alcouffe, P.; Ladavière, C.; Gérard, J-Fois.; Lortie, Frédéric.;.; Bernard, Julien.; Heterocomplementary H-Bonding RAFT Agents as Tools for the Preparation of Supramolecular Miktoarm Star Copolymers. Macromolecules 2010, 43, 5981–5988. DOI: 10.1021/ma101044y.
  • Destarac, M.; Charmot, D.; Franck, X.; Zard, S. Z. Dithiocarbamates as Universal Reversible Addition‐Fragmentation Chain Transfer Agents. Macromol. Rapid Commun. 2000, 21, 1035–1039. DOI: 10.1002/1521-3927(20001001)21:15 < 1035::AID-MARC1035 > 3.0.CO;2-5.
  • Benaglia, M.; Chen, M.; Chong, Y. K.; Moad, G.; Rizzardo, E.; Thang, S. H. Polystyrene-Block-Poly(Vinyl Acetate) through the Use of a Switchable RAFT Agent. Macromolecules 2009, 42, 9384–9386. DOI: 10.1021/ma9021086.
  • Benaglia, M.; Chiefari, J.; Chong, Y. K.; Moad, G.; Rizzardo, E.; Thang, S. H. Universal (Switchable) RAFT Agents. J. Am. Chem. Soc. 2009, 13, 6914–6915. DOI: 10.1021/ja901955n.
  • Yamago, Shigeru.; Iida, Kazunori.; Yoshida, Jun-ichi. Tailored Synthesis of Structurally Defined Polymers by Organotellurium-Mediated Living Radical Polymerization (TERP): Synthesis of Poly(Meth)Acrylate Derivatives and Their Di- and Triblock Copolymers. J. Am. Chem. Soc. 2002, 124, 13666–13667. DOI: 10.1021/ja027599i.
  • Yamago, S.; Ray, B.; Iida, K.; Yoshida, J.; Tada, T.; Yoshizawa, K.; Kwak, Y.; Goto, A.; Fukuda, T. Highly Versatile Organostibine Mediators for Living Radical Polymerization. J. Am. Chem. Soc. 2004, 126, 13908–13909. DOI: 10.1021/ja044787v.
  • Xia, J. H.; Paik, H. J.; Matyjaszewski, K. Polymerization of Vinyl Acetate Promoted by Iron Complexes. Macromolecules 1999, 32, 8310–8314. DOI: 10.1021/ma991075u.
  • Wakioka, M.; Baek, K. Y.; Ando, T.; Kamigaito, M.; Sawamoto, M. Pseudopolyrotaxanes Made to Order: Cucurbituril Threaded on Polyviologen. Macromolecules 2002, 35, 330–330. DOI: 10.1021/ma0115444.
  • Debuigne, A.; Caille, J. R.; Jerome, R. Highly Efficient Cobalt-Mediated Radical Polymerization of Vinyl Acetate. Angew Chem Int Ed 2005, 44, 1101–1104. DOI: 10.1002/anie.200461333.
  • Debuigne, A.; Caille, J.-R.; Detrembleur, C.; Jerome, R. Effective Cobalt Mediation of the Radical Polymerization of Vinyl Acetate in Suspension. Angew. Chem. Int. Ed. 2005, 44, 3439–3442. DOI: 10.1002/anie.200500112.
  • Kaneyoshi, H.; Matyjaszewski, K. Effect of Ligand and n-Butyl Acrylate on Cobalt-Mediated Radical Polymerization of Vinyl Acetate. Macromolecules 2005, 38, 8163–8169. DOI: 10.1021/ma051433v.
  • Peng, C. H.; Scricco, J.; Li, S.; Fryd, M.; Wayland, B. B. Organo-Cobalt Mediated Living Radical Polymerization of Vinyl Acetate. Macromolecules 2008, 41, 2368–2373. DOI: 10.1021/ma702500b.
  • Patel, V. K.; Mishra, A. K.; Vishwakarma, N. K.; Biswas, C. S.; Ray, B. (S)-2-(Ethyl Propionate)-(O-Ethyl Xanthate) and (S)-2-(Ethyl Isobutyrate)-(O-Ethyl Xanthate)-Mediated RAFT Polymerization of N-Vinylpyrrolidone. Polym. Bull. 2010, 65, 97–110. DOI: 10.1007/s00289-009-0185-1.
  • Patel, V. K.; Vishwakarma, N. K.; Mishra, A. K.; Biswas, C. S.; Maiti, P.; Ray, B. Synthesis of Alkyne‐Terminated Xanthate RAFT Agents and Their Uses for the Controlled Radical Polymerization of N‐Vinylpyrrolidone and the Synthesis of Its Block Copolymer Using Click Chemistry. J. Appl. Polym. Sci. 2013, 127, 4305–4317. DOI: 10.1002/app.38037.
  • Patel, V. K.; Vishwakarma, N. K.; Singh, S.; Mitra, K.; Ramesh, K.; Mishra, N.; Ray, B. Synthesis of Fluorescence Poly(N-Vinylpyrrolidone) via Click Chemistry Using Azide-Terminated Xanthate Mediator (S)-2-(4-Azidobutyl Propionate)-(O-Ethyl Xanthate). Int. J. Polym. Mater. Polym. Biomater 2016, 65, 269–276. DOI: 10.1080/00914037.2015.1119682.
  • Vishwakarma, S.; Kumari, A.; Mitra, K.; Singh, S.; Singh, R.; Singh, J.; Sen Gupta, S. K.; Ray, B. L‐Menthol‐Based Initiators for Atom Transfer Radical Polymerization of Styrene. J. Appl. Polym. Sci. 2019, 136, 47964–47974. DOI: 10.1002/app.47964.

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