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Journal articles on the topic 'Nitroxide-Mediated Radical Polymerization'

Author: Grafiati

Published: 4 June 2021

Last updated: 2 February 2022

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1

Chen, Mao, Honghong Gong, and Yu Gu. "Controlled/Living Radical Polymerization of Semifluorinated (Meth)acrylates." Synlett 29, no. 12 (April 18, 2018): 1543–51. http://dx.doi.org/10.1055/s-0036-1591974.

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Fluorinated polymers are important materials for applications in many areas. This article summarizes the development of controlled/living radical polymerization (CRP) of semifluorinated (meth)acrylates, and briefly introduces their reaction mechanisms. While the classical CRP such as atom transfer radical polymerization (ATRP), reversible addition-fragmentation chain transfer (RAFT) polymerization and nitroxide-mediated radical polymerization (NMP) have promoted the preparation of semifluorinated polymers with tailor-designed architectures, recent development of photo-CRP has led to unprecedented accuracy and monomer scope. We expect that synthetic advances will facilitate the engineering of advanced fluorinated materials with unique properties.1 Introduction2 Atom Transfer Radical Polymerization3 Reversible Addition-Fragmentation Chain Transfer Polymerization4 Nitroxide-Mediated Radical Polymerization5 Photo-CRP Mediated with Metal Complexes6 Metal-free Photo-CRP7 Conclusion

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2

Wakamatsu, Junpei, Masahiro Kawasaki, Per B. Zetterlund, and Masayoshi Okubo. "Nitroxide-Mediated Radical Polymerization in Microemulsion." Macromolecular Rapid Communications 28, no. 24 (December 14, 2007): 2346–53. http://dx.doi.org/10.1002/marc.200700576.

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3

Sill, Kevin, and Todd Emrick. "Nitroxide-Mediated Radical Polymerization from CdSe Nanoparticles." Chemistry of Materials 16, no. 7 (April 2004): 1240–43. http://dx.doi.org/10.1021/cm035077b.

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4

Li, Jieai, Xiulin Zhu, Jian Zhu, and Zhenping Cheng. "Imidazoline Nitroxide‐Mediated Radical Polymerization of Styrene." Journal of Macromolecular Science, Part A 44, no. 1 (January 2007): 41–46. http://dx.doi.org/10.1080/10601320601044401.

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5

Cano-Valdez, Andrés, Enrique Saldívar-Guerra, Roberto González-Blanco, Michael F. Cunningham, and Jorge Herrera-Ordóñez. "Nitroxide Mediated Radical Emulsion Polymerization: Mathematical Modeling." Macromolecular Symposia 374, no. 1 (August 2017): 1600150. http://dx.doi.org/10.1002/masy.201600150.

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6

Cunningham, M. F., K. Tortosa, J. W. Ma, K. B. McAuley, B. Keoshkerian, and M. K. Georges. "Nitroxide mediated living radical polymerization in miniemulsion." Macromolecular Symposia 182, no. 1 (June 2002): 273–82. http://dx.doi.org/10.1002/1521-3900(200206)182:1<273::aid-masy273>3.0.co;2-l.

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7

Ruehl, Jean, Niwat Ningnuek, Thanchanok Thongpaisanwong, and Rebecca Braslau. "Cyclic alkoxyamines for nitroxide-mediated radical polymerization." Journal of Polymer Science Part A: Polymer Chemistry 46, no. 24 (December 15, 2008): 8049–69. http://dx.doi.org/10.1002/pola.23103.

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8

Fu, Yao, Michael F. Cunningham, and Robin A. Hutchinson. "Modeling of Nitroxide-Mediated Semibatch Radical Polymerization." Macromolecular Reaction Engineering 1, no. 2 (February 7, 2007): 243–52. http://dx.doi.org/10.1002/mren.200600024.

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9

Georges, Michael K., R. Andrew Kee, Richard P. N. Veregin, Gordon K. Hamer, and Peter M. Kazmaier. "Nitroxide mediated free radical polymerization process - autopolymerization." Journal of Physical Organic Chemistry 8, no. 4 (April 1995): 301–5. http://dx.doi.org/10.1002/poc.610080413.

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10

Grubbs, Robert B. "Nitroxide-Mediated Radical Polymerization: Limitations and Versatility." Polymer Reviews 51, no. 2 (April 22, 2011): 104–37. http://dx.doi.org/10.1080/15583724.2011.566405.

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11

Gibbons, Orla, William M. Carroll, Fawaz Aldabbagh, Per B. Zetterlund, and Bunichiro Yamada. "Nitroxide-Mediated Radical Polymerization ofN-tert-Butylacrylamide." Macromolecular Chemistry and Physics 209, no. 23 (December 1, 2008): 2434–44. http://dx.doi.org/10.1002/macp.200800358.

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12

Colwell, John M., James P. Blinco, Courtney Hulbert, Kathryn E. Fairfull-Smith, and Steven E. Bottle. "A Profluorescent Azaphenalene Nitroxide for Nitroxide-Mediated Polymerization." Australian Journal of Chemistry 64, no. 4 (2011): 426. http://dx.doi.org/10.1071/ch10404.

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A novel nitroxide‐mediated polymerization (NMP) control agent; 1,1,3,3‐tetramethyl‐2,3‐dihydro‐2‐azaphenalen‐2‐yloxyl (TMAO), was used in the free‐radical polymerization of styrene. The conversion of styrene during NMP was studied using FT‐Raman spectroscopy and the effectiveness of TMAO as a NMP control agent was assessed by GPC analysis. Fidelity of the TMAO‐alkoxyamine end‐group on the synthesized polymers was confirmed by GPC, UV‐Vis and fluorescence spectroscopic analyses. Comparison to the well known NMP control agent, TEMPO was made. TMAO showed control of molecular weight approaching that of TEMPO. Attempts to improve the properties of TMAO as an NMP control agent by synthesizing an analogue with bulkier substituents around the nitroxide did not generate the target molecule but demonstrated some of the interesting chemistry of the azaphenalene ring system.

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13

Rizzardo, Ezio, and David H. Solomon. "On the Origins of Nitroxide Mediated Polymerization (NMP) and Reversible Addition–Fragmentation Chain Transfer (RAFT)." Australian Journal of Chemistry 65, no. 8 (2012): 945. http://dx.doi.org/10.1071/ch12194.

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The early experiments on radical polymerization, which were to lead to a study of nitroxide trapping of the initiation step and the interest in defect groups, particularly the macromonomers formed by termination by disproportionation, are discussed. Results from the nitroxide trapping clearly show that the initiation step ranges from simple clean addition to the head of the monomer, to complex addition/abstraction reactions. Careful selection of the monomer/initiation system is emphasized with particular reference to two common monomers, styrene and methyl methacrylate, and two initiating radicals, t-butoxy and benzoyloxy. The discovery of nitroxide mediated polymerization (NMP) from observations made during the nitroxide trapping work is reported and the ability to have a living radical system demonstrated with numerous examples. Similarly, the study of the copolymerization of macromonomers, formed by disproportionation of the propagating chains, is discussed with the discovery of β-scission and an early form of addition–fragmentation reported. The evolution of reversible addition–fragmentation chain transfer (RAFT) to a highly versatile and commercially attractive radical system is reported and the detailed chemistry behind the discovery of this living radical system discussed. Both NMP and RAFT enable the synthesis of structures not previously possible by radical polymerization and in some cases not possible by any other process.

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14

Domenichelli, Ilaria, Sanjib Banerjee, Sara Taddei, Elisa Martinelli, Elisa Passaglia, and Bruno Ameduri. "Styrene and substituted styrene grafted functional polyolefins via nitroxide mediated polymerization." Polymer Chemistry 9, no. 3 (2018): 307–14. http://dx.doi.org/10.1039/c7py01693j.

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Functionalized polyolefins bearing alkoxyamines derived from a nitroxide radical coupling reaction were successfully used as macroinitiators to graft polystyrene or substituted polystyrene brushes via nitroxide mediated polymerization.

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15

Lowe, A. B., and C. L. McCormick. "Homogeneous Controlled Free Radical Polymerization in Aqueous Media." Australian Journal of Chemistry 55, no. 7 (2002): 367. http://dx.doi.org/10.1071/ch02053.

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The ability to conduct controlled radical polymerizations (CRP) in homogeneous aqueous media is discussed. Three main techniques, namely stable free radical polymerization (SFRP), with an emphasis on nitroxide-mediated polymerization (NMP), atom transfer radical polymerization (ATRP) and reversible addition-fragmentation chain transfer polymerization (RAFT) are examined. No examples exist of homogeneous aqueous NMP polymerization, but mixed water/solvent systems are discussed with specific reference to the NMP of sodium 4-styrenesulfonate. Aqueous ATRP is possible, although monomer choice is limited to methacrylates and certain styrenics. Finally, homogeneous aqueous RAFT polymerizations are examined. We demonstrate the greater versatility of this technique, at least in terms of monomer variety, by discussing the controlled polymerization of charged and neutral acrylamido monomers and of a series of ionic styrenic monomers. Many of these monomers cannot/have not been polymerized by either NMP or ATRP.

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16

Zetterlund, Per B. "Nitroxide-Mediated Radical Polymerization in Nanoreactors: Can Dilution or Increased Nitroxide Concentration Provide Benefits Similar to Compartmentalization?" Australian Journal of Chemistry 63, no. 8 (2010): 1195. http://dx.doi.org/10.1071/ch10063.

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Compartmentalization of a nitroxide-mediated radical polymerization system can lead to improved levels of both control and livingness, but at the cost of a reduced polymerization rate. Improved control is a result of the confined space effect on deactivation, whereas improved livingness stems from the segregation effect on bimolecular termination. Modelling and simulations have been carried out for the systems styrene/2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) and styrene/2,2,5-trimethyl-4-phenyl-3-azahexane-3-oxy (TIPNO) using the respective nitroxide-based polystyrene macroinitaitors (alkoxyamines) at 125°C to elucidate whether similar benefits can be obtained in the corresponding bulk polymerizations by merely diluting the systems or by addition of extra free nitroxide. The results have shown that neither approach leads to simultaneous improvement in control and livingness relative to the corresponding bulk systems, thus accentuating the merits of compartmentalization in nanoreactors.

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17

Zetterlund, Per B. "Nitroxide-Mediated Radical Polymerization in Dispersed Systems: Compartmentalization and Nitroxide Partitioning." Macromolecular Theory and Simulations 19, no. 1 (November 10, 2009): 11–23. http://dx.doi.org/10.1002/mats.200900051.

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18

Li, Jieai, Xiulin Zhu, Jian Zhu, and Zhenping Cheng. "Microwave-assisted nitroxide-mediated radical polymerization of styrene." Radiation Physics and Chemistry 75, no. 2 (February 2006): 253–58. http://dx.doi.org/10.1016/j.radphyschem.2005.06.006.

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19

Cao, Jizhuang, Junpo He, Chengming Li, and Yuliang Yang. "Nitroxide-Mediated Radical Polymerization of Styrene in Emulsion." Polymer Journal 33, no. 1 (January 2001): 75–80. http://dx.doi.org/10.1295/polymj.33.75.

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20

Quinn, Jeffrey D., and Richard A. Register. "Nitroxide-mediated radical polymerization ofN-ethyl-2-vinylcarbazole." Polymers for Advanced Technologies 19, no. 6 (2008): 556–59. http://dx.doi.org/10.1002/pat.1103.

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21

Le Du, Yann, Laurent Binet, Patrick Hémery, and Lucien Marx. "Proton-controlled nitroxide mediated radical polymerization of styrene." Journal of Polymer Science Part A: Polymer Chemistry 50, no. 14 (April 16, 2012): 2871–77. http://dx.doi.org/10.1002/pola.26064.

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22

Colwell, John M., James P. Blinco, Courtney Hulbert, Kathryn E. Fairfull-Smith, and Steven E. Bottle. "Corrigendum to: A Profluorescent Azaphenalene Nitroxide for Nitroxide-Mediated Polymerization." Australian Journal of Chemistry 64, no. 11 (2011): 1539. http://dx.doi.org/10.1071/ch10404_co.

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A novel nitroxide-mediated polymerization (NMP) control agent; 1,1,3,3-tetramethyl-2,3-dihydro-2-azaphenalen-2-yloxyl (TMAO), was used in the free-radical polymerization of styrene. The conversion of styrene during NMP was studied using FT-Raman spectroscopy and the effectiveness of TMAO as a NMP control agent was assessed by GPC analysis. Fidelity of the TMAO-alkoxyamine end-group on the synthesized polymers was confirmed by GPC, UV-Vis and fluorescence spectroscopic analyses. Comparison to the well known NMP control agent, TEMPO was made. TMAO showed control of molecular weight approaching that of TEMPO. Attempts to improve the properties of TMAO as an NMP control agent by synthesizing an analogue with bulkier substituents around the nitroxide did not generate the target molecule but demonstrated some of the interesting chemistry of the azaphenalene ring system.

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23

Li, Weikun, Chunhui Bao, Roger A. E. Wright, and Bin Zhao. "Synthesis of mixed poly(ε-caprolactone)/polystyrene brushes from Y-initiator-functionalized silica particles by surface-initiated ring-opening polymerization and nitroxide-mediated radical polymerization." RSC Adv. 4, no. 36 (2014): 18772–81. http://dx.doi.org/10.1039/c4ra02429j.

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This article reports the synthesis of mixed brushes by ring-opening polymerization of ε-caprolactone and nitroxide-mediated radical polymerization of styrene from Y-initiator-functionalized silica particles.

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24

Asteasuain, Mariano. "Deterministic Approaches for Simulation of Nitroxide-Mediated Radical Polymerization." International Journal of Polymer Science 2018 (August 9, 2018): 1–16. http://dx.doi.org/10.1155/2018/7803702.

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Since its development in the last decades, controlled radical polymerization (CRP) has become a very promising option for the synthesis of polymers with controlled structure. The design and production of tailor-made materials can be significantly improved by developing models capable of predicting the polymer properties from the operating conditions. Nitroxide-mediated polymerization (NMP) was the first of the three main variants of CRP to be discovered. Although it has lost preference over the years against other CRP alternatives, NMP is still an attractive synthesis method because of its simple experimental implementation and environmental friendliness. This review focuses on deterministic methods employed in mathematical models of NMP. It presents an overview of the different techniques that have been reported for modelling NMP processes in homogeneous and heterogeneous media, covering from the prediction of average properties to the latest techniques for modelling univariate and multivariate distributions of polymer properties. Finally, an outlook of model-based design studies of NMP processes is given.

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25

Huang, Jian-ying, Jia-ming Zhuang, and You-si Zou. "Substituent effects of accelerator on nitroxide-mediated radical polymerization." Macromolecular Research 19, no. 8 (July 19, 2011): 757–63. http://dx.doi.org/10.1007/s13233-011-0808-x.

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26

Alemdar, Neslihan, A. Tuncer Erciyes, and Yusuf Yagci. "Styrenation of triglyceride oil by nitroxide mediated radical polymerization." Progress in Organic Coatings 66, no. 2 (October 2009): 99–106. http://dx.doi.org/10.1016/j.porgcoat.2009.06.006.

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27

Prodpran, T., V. L. Dimonie, E. D. Sudol, and M. S. El-Aasser. "Nitroxide-mediated living free radical miniemulsion polymerization of styrene." Macromolecular Symposia 155, no. 1 (April 2000): 1–14. http://dx.doi.org/10.1002/1521-3900(200004)155:1<1::aid-masy1>3.0.co;2-1.

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28

Wang, Yanxiang, Robin A. Hutchinson, and Michael F. Cunningham. "A Semi-Batch Process for Nitroxide Mediated Radical Polymerization." Macromolecular Materials and Engineering 290, no. 4 (April 19, 2005): 230–41. http://dx.doi.org/10.1002/mame.200400273.

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29

Delaittre, Guillaume, Jutta Rieger, and Bernadette Charleux. "Nitroxide-Mediated Living/Controlled Radical Polymerization ofN,N-Diethylacrylamide." Macromolecules 44, no. 3 (February 8, 2011): 462–70. http://dx.doi.org/10.1021/ma102569e.

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30

Pan, Gaofeng, E. David Sudol, Victoria L. Dimonie, and Mohamed S. El-Aasser. "Nitroxide-Mediated Living Free Radical Miniemulsion Polymerization of Styrene." Macromolecules 34, no. 3 (January 2001): 481–88. http://dx.doi.org/10.1021/ma000922m.

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31

Zetterlund, Per B., and Masayoshi Okubo. "Compartmentalization in Nitroxide-Mediated Radical Polymerization in Dispersed Systems." Macromolecules 39, no. 26 (December 2006): 8959–67. http://dx.doi.org/10.1021/ma060841b.

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32

Marestin, Catherine, Catherine Noël, Alain Guyot, and Jérôme Claverie. "Nitroxide Mediated Living Radical Polymerization of Styrene in Emulsion." Macromolecules 31, no. 12 (June 1998): 4041–44. http://dx.doi.org/10.1021/ma9710951.

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33

Yoshida, Eri. "Nitroxide-mediated photo-living radical polymerization of vinyl acetate." Colloid and Polymer Science 288, no. 1 (October 17, 2009): 73–78. http://dx.doi.org/10.1007/s00396-009-2123-z.

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34

Grassl, Bruno, Gérald Clisson, Abdel Khoukh, and Laurent Billon. "Nitroxide-mediated radical polymerization of acrylamide in water solution." European Polymer Journal 44, no. 1 (January 2008): 50–58. http://dx.doi.org/10.1016/j.eurpolymj.2007.10.019.

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35

Cameron, Neil R., Olivier Lagrille, Peter A. Lovell, and Bencha Thongnuanchan. "A Nitroxide for Effecting Controlled Nitroxide-Mediated Radical Polymerization at Temperatures ≤90 °C." ACS Macro Letters 1, no. 11 (October 12, 2012): 1262–65. http://dx.doi.org/10.1021/mz300464c.

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36

Bothe, Marc, and Gudrun Schmidt-Naake. "Nitroxide-Mediated Radical Polymerization with Bisaminooxy Compounds as Initiators– Controlled Biradical Polymerization." Macromolecular Chemistry and Physics 205, no. 2 (January 2004): 208–16. http://dx.doi.org/10.1002/macp.200300022.

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37

Kuo, Teng-Yuan, Li-An Chien, Ya-Chi Chang, Shuang-Yu Liou, and Che-Chien Chang. "Synthetic mimics of carbohydrate-based anticancer vaccines: preparation of carbohydrate polymers bearing unimolecular trivalent carbohydrate ligands by controlled living radical polymerization." RSC Adv. 4, no. 87 (2014): 47066–75. http://dx.doi.org/10.1039/c4ra04907a.

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38

Yoshida, Eri. "Nitroxide-Mediated Photo-Controlled/Living Radical Polymerization of Methacrylic Acid." Open Journal of Polymer Chemistry 03, no. 01 (2013): 16–22. http://dx.doi.org/10.4236/ojpchem.2013.31004.

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39

Kermagoret, Anthony, and Didier Gigmes. "Combined nitroxide mediated radical polymerization techniques for block copolymer synthesis." Tetrahedron 72, no. 48 (December 2016): 7672–85. http://dx.doi.org/10.1016/j.tet.2016.07.002.

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40

Couvreur, Laurence, Catherine Lefay, Joël Belleney, Bernadette Charleux, Olivier Guerret, and Stéphanie Magnet. "First Nitroxide-Mediated Controlled Free-Radical Polymerization of Acrylic Acid." Macromolecules 36, no. 22 (November 2003): 8260–67. http://dx.doi.org/10.1021/ma035043p.

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41

Mignard, Emmanuel, Thierry Leblanc, Denis Bertin, Olivier Guerret, and Wayne F. Reed. "Online Monitoring of Controlled Radical Polymerization: Nitroxide-Mediated Gradient Copolymerization." Macromolecules 37, no. 3 (February 2004): 966–75. http://dx.doi.org/10.1021/ma035589b.

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42

Búcsiová, L'ubica, Meizhen Yin, ŠTefan Chmela, and Wolf D. Habicher. "Nitroxide‐mediated Living Radical Polymerization of Styrene with Fluorescent Initiator." Journal of Macromolecular Science, Part A 45, no. 9 (July 2008): 761–68. http://dx.doi.org/10.1080/10601320802222897.

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43

Schierholz, K., M. Givehchi, P. Fabre, F. Nallet, E. Papon, O. Guerret, and Y. Gnanou. "Acrylamide-Based Amphiphilic Block Copolymers via Nitroxide-Mediated Radical Polymerization." Macromolecules 36, no. 16 (August 2003): 5995–99. http://dx.doi.org/10.1021/ma0300387.

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44

Lutz, Jean-François, Patrick Lacroix-Desmazes, and Bernard Boutevin. "The Persistent Radical Effect in Nitroxide Mediated Polymerization: Experimental Validity." Macromolecular Rapid Communications 22, no. 3 (February 2001): 189–93. http://dx.doi.org/10.1002/1521-3927(200102)22:3<189::aid-marc189>3.0.co;2-x.

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45

Nesvadba, Peter, Lucienne Bugnon, and Rosemarie Sift. "New 7-membered diazepanone alkoxyamines for nitroxide-mediated radical polymerization." Journal of Polymer Science Part A: Polymer Chemistry 42, no. 13 (2004): 3332–41. http://dx.doi.org/10.1002/pola.20200.

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46

Lang, Andreas S., Franz René Kogler, Michael Sommer, Ulrich Wiesner, and Mukundan Thelakkat. "Semiconductor Dendritic-Linear Block Copolymers by Nitroxide Mediated Radical Polymerization." Macromolecular Rapid Communications 30, no. 14 (July 3, 2009): 1243–48. http://dx.doi.org/10.1002/marc.200900203.

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47

Pu, Da Wei, Frank P. Lucien, and Per B. Zetterlund. "Nitroxide-mediated radical polymerization of carbon dioxide-expanded methyl methacrylate." Journal of Polymer Science Part A: Polymer Chemistry 48, no. 23 (October 13, 2010): 5636–41. http://dx.doi.org/10.1002/pola.24343.

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48

Grubbs, Robert B., Jakub K. Wegrzyn, and Qing Xia. "One-step synthesis of alkoxyamines for nitroxide-mediated radical polymerization." Chemical Communications, no. 1 (2005): 80. http://dx.doi.org/10.1039/b413358g.

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49

Yoshida, Eri. "Nitroxide-mediated photo-controlled/living radical polymerization of ethyl acrylate." Colloid and Polymer Science 289, no. 10 (May 12, 2011): 1127–32. http://dx.doi.org/10.1007/s00396-011-2435-7.

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50

Chmela, Š., and L’ Hrčková. "Nitroxide mediated styrene radical polymerization using a fluorescence marked mediator." European Polymer Journal 45, no. 9 (September 2009): 2580–86. http://dx.doi.org/10.1016/j.eurpolymj.2009.06.019.

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