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Journal articles on the topic 'MADIX controlled radical polymerization'

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Published: 25 May 2024

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1

Etchenausia, Laura, Abdel Khoukh, Elise Deniau Lejeune, and Maud Save. "RAFT/MADIX emulsion copolymerization of vinyl acetate and N-vinylcaprolactam: towards waterborne physically crosslinked thermoresponsive particles." Polymer Chemistry 8, no. 14 (2017): 2244–56. http://dx.doi.org/10.1039/c7py00221a.

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2

Destarac, Mathias, Wojciech Bzducha, Daniel Taton, Isabelle Gauthier-Gillaizeau, and Samir Z. Zard. "Xanthates as Chain-Transfer Agents in Controlled Radical Polymerization (MADIX): Structural Effect of the O-Alkyl Group." Macromolecular Rapid Communications 23, no. 17 (December 2002): 1049–54. http://dx.doi.org/10.1002/marc.200290002.

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3

Destarac, Mathias, Juliette Ruchmann-Sternchuss, Eric Van Gramberen, Xavier Vila, and Samir Z. Zard. "α-Amido Trifluoromethyl Xanthates: A New Class of RAFT/MADIX Agents." Molecules 29, no. 10 (May 7, 2024): 2174. http://dx.doi.org/10.3390/molecules29102174.

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Xanthates have long been described as poor RAFT/MADIX agents for styrene polymerization. Through the determination of chain transfer constants to xanthates, this work demonstrated beneficial capto-dative substituent effects for the leaving group of a new series of α-amido trifluoromethyl xanthates, with the best effect observed with trifluoroacetyl group. The previously observed Z-group activation with a O-trifluoroethyl group compared to the O-ethyl counterpart was quantitatively established with Cex = 2.7 (3–4 fold increase) using the SEC peak resolution method. This study further confirmed the advantageous incorporation of trifluoromethyl substituents to activate xanthates in radical chain transfer processes and contributed to identify the most reactive xanthate reported to date for RAFT/MADIX polymerization of styrene.

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4

Seiler, Lucie, Julien Loiseau, Frédéric Leising, Pascal Boustingorry, Simon Harrisson, and Mathias Destarac. "Acceleration and improved control of aqueous RAFT/MADIX polymerization of vinylphosphonic acid in the presence of alkali hydroxides." Polymer Chemistry 8, no. 25 (2017): 3825–32. http://dx.doi.org/10.1039/c7py00747g.

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5

Wang, Pucheng, Jingwen Dai, Lei Liu, Qibao Dong, Hu Wang, and Ruke Bai. "Synthesis and properties of a well-defined copolymer of chlorotrifluoroethylene and N-vinylpyrrolidone by xanthate-mediated radical copolymerization under 60Co γ-ray irradiation." Polym. Chem. 5, no. 21 (2014): 6358–64. http://dx.doi.org/10.1039/c4py00902a.

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6

Theis, Alexander, Thomas P. Davis, Martina H. Stenzel, and Christopher Barner-Kowollik. "Probing the reaction kinetics of vinyl acetate free radical polymerization via living free radical polymerization (MADIX)." Polymer 47, no. 4 (February 2006): 999–1010. http://dx.doi.org/10.1016/j.polymer.2005.12.054.

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7

Matyjaszewski, Krzysztof. "Controlled radical polymerization." Current Opinion in Solid State and Materials Science 1, no. 6 (December 1996): 769–76. http://dx.doi.org/10.1016/s1359-0286(96)80101-x.

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8

Gaynor, Scott, Dorota Greszta, Daniela Mardare, Mircea Teodorescu, and Krzysztof Matyjaszewski. "Controlled Radical Polymerization." Journal of Macromolecular Science, Part A 31, no. 11 (January 1994): 1561–78. http://dx.doi.org/10.1080/10601329408545868.

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9

Bertin, Denis, and Bernard Boutevin. "Controlled radical polymerization." Polymer Bulletin 37, no. 3 (September 1996): 337–44. http://dx.doi.org/10.1007/bf00318066.

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10

Zard, Samir Z. "The Genesis of the Reversible Radical Addition–Fragmentation–Transfer of Thiocarbonylthio Derivatives from the Barton–McCombie Deoxygenation: A Brief Account and Some Mechanistic Observations." Australian Journal of Chemistry 59, no. 10 (2006): 663. http://dx.doi.org/10.1071/ch06263.

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The observations and reasoning leading to the discovery of the degenerative transfer of xanthates and related thiocarbonylthio derivatives are briefly described. A few synthetic applications are presented, and the consequences on the emergence of the RAFT and MADIX polymerization technologies as well as some mechanistic aspects are briefly discussed.

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11

Lou, Yu, Dong Jian Shi, Wei Fu Dong, and Ming Qing Chen. "Synthesis and Self-Assemble Behavior of Block Copolymerization of Vinyl Acetate and N-Vinylacetamide." Advanced Materials Research 645 (January 2013): 10–14. http://dx.doi.org/10.4028/www.scientific.net/amr.645.10.

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Polymerizations of VAc was carried out using AIBN as the initiator and DIP as the MADIX agent precursor. Then, block copolymer PVAc-b-PNVA had been synthesized by RAFT radical polymerization in the presence of PVAc-DIP as macro CTA. The length of blocks could be tuned by changing the molar ratio of NVA and VAc. Block copolymer PVAc-b-PNVA self-assembled into micelles in solution, and underwent microphase separation in bulk state.

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12

Severin, K., M. Haas, E. Solari, O. Nguyen, S. Gautier, and R. Scopelliti. "RT-Controlled Radical Polymerization." Synfacts 2006, no. 5 (May 2006): 0446. http://dx.doi.org/10.1055/s-2006-934385.

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13

Matyjaszewski, Krzysztof, and James Spanswick. "Controlled/living radical polymerization." Materials Today 8, no. 3 (March 2005): 26–33. http://dx.doi.org/10.1016/s1369-7021(05)00745-5.

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14

Pan, Xiangcheng, Mehmet Atilla Tasdelen, Joachim Laun, Thomas Junkers, Yusuf Yagci, and Krzysztof Matyjaszewski. "Photomediated controlled radical polymerization." Progress in Polymer Science 62 (November 2016): 73–125. http://dx.doi.org/10.1016/j.progpolymsci.2016.06.005.

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15

Tasdelen, Mehmet Atilla, Mustafa Uygun, and Yusuf Yagci. "Photoinduced Controlled Radical Polymerization." Macromolecular Rapid Communications 32, no. 1 (August 31, 2010): 58–62. http://dx.doi.org/10.1002/marc.201000351.

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16

Bon, Stefan A. F., Michiel Bosveld, Bert Klumperman, and Anton L. German. "Controlled Radical Polymerization in Emulsion." Macromolecules 30, no. 2 (January 1997): 324–26. http://dx.doi.org/10.1021/ma961003s.

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17

Matyjaszewski, Krzysztof, Scott Gaynor, Dorota Greszta, Daniela Mardare, and Takeo Shigemoto. "?Living? and controlled radical polymerization." Journal of Physical Organic Chemistry 8, no. 4 (April 1995): 306–15. http://dx.doi.org/10.1002/poc.610080414.

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18

Whitfield, Richard, Nghia P. Truong, and Athina Anastasaki. "Sequence-controlled Polymers via Controlled Radical Polymerization." CHIMIA International Journal for Chemistry 73, no. 4 (April 24, 2019): 331. http://dx.doi.org/10.2533/chimia.2019.331.

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19

Caille, Jean-Raphaël, Antoine Debuigne, and Robert Jérôme. "Controlled Radical Polymerization of Styrene by Quinone Transfer Radical Polymerization (QTRP)." Macromolecules 38, no. 1 (January 2005): 27–32. http://dx.doi.org/10.1021/ma048561o.

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20

Matyjaszewski, Krzysztof. "Transition Metal Catalysis in Controlled Radical Polymerization: Atom Transfer Radical Polymerization." Chemistry - A European Journal 5, no. 11 (November 5, 1999): 3095–102. http://dx.doi.org/10.1002/(sici)1521-3765(19991105)5:11<3095::aid-chem3095>3.0.co;2-#.

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21

Wang, Lu, Wang, and Bai. "A New Strategy for the Synthesis of Fluorinated Polyurethane." Polymers 11, no. 9 (September 2, 2019): 1440. http://dx.doi.org/10.3390/polym11091440.

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An alternating fluorinated copolymer based on chlorotrifluoroethylene (CTFE) and butyl vinyl ether (BVE) was synthesized by RAFT/MADIX living/controlled polymerization in the presence of S-benzyl O-ethyl dithiocarbonate (BEDTC). Then, using the obtained poly(CTFE-alt-BVE) as a macro chain transfer agent (macro-CTA), a block copolymer was prepared by chain extension polymerization of vinyl acetate (VAc). After a basic methanolysis process, the poly(vinyl acetate) (PVAc) block was transferred into poly(vinyl alcohol) (PVA). Finally, a novel fluorinated polyurethane with good surface properties due to the mobility of the flexible fluorinated polymer chains linked to the network was obtained via reaction of the copolymer bearing the blocks of PVA with isophorone diisocyanate (IPDI) as a cross-linking agent.

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22

Grimaud, Thomas, and Krzysztof Matyjaszewski. "Controlled/“Living” Radical Polymerization of Methyl Methacrylate by Atom Transfer Radical Polymerization." Macromolecules 30, no. 7 (April 1997): 2216–18. http://dx.doi.org/10.1021/ma961796i.

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23

Xia, Jianhui, and Krzysztof Matyjaszewski. "Controlled/“Living” Radical Polymerization. Atom Transfer Radical Polymerization Using Multidentate Amine Ligands." Macromolecules 30, no. 25 (December 1997): 7697–700. http://dx.doi.org/10.1021/ma971009x.

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24

Higashimura, Hideyuki. "Radical-Controlled Oxidative Polymerization of Phenols." Journal of Synthetic Organic Chemistry, Japan 63, no. 10 (2005): 970–81. http://dx.doi.org/10.5059/yukigoseikyokaishi.63.970.

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25

UEDA, Naoki. "Controlled Radical Polymerization with Iodine Compounds." Kobunshi 48, no. 7 (1999): 513. http://dx.doi.org/10.1295/kobunshi.48.513.

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26

SHIGA, Akinobu. "“Radical -Controlled”Oxidative Polymerization of Phenols." Kobunshi 49, no. 4 (2000): 236. http://dx.doi.org/10.1295/kobunshi.49.236.

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27

Matyjaszewski, K., and E. Chernikova. "New trends in controlled radical polymerization." Polymer Science Series C 57, no. 1 (July 7, 2015): 1–2. http://dx.doi.org/10.1134/s1811238215010075.

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28

Pan, Xiangcheng, Marco Fantin, Fang Yuan, and Krzysztof Matyjaszewski. "Externally controlled atom transfer radical polymerization." Chemical Society Reviews 47, no. 14 (2018): 5457–90. http://dx.doi.org/10.1039/c8cs00259b.

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ATRP can be externally controlled by electrical current, light, mechanical forces and various chemical reducing agents. The mechanistic aspects and preparation of polymers with complex functional architectures and their applications are critically reviewed.

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29

Cuthbert, Julia, Anna C. Balazs, Tomasz Kowalewski, and Krzysztof Matyjaszewski. "STEM Gels by Controlled Radical Polymerization." Trends in Chemistry 2, no. 4 (April 2020): 341–53. http://dx.doi.org/10.1016/j.trechm.2020.02.002.

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30

Bruno, Ameduri. "Controlled Radical (Co)polymerization of Fluoromonomers." Macromolecules 43, no. 24 (December 28, 2010): 10163–84. http://dx.doi.org/10.1021/ma1019297.

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31

Ameduri, Bruno. "Controlled Radical (Co)polymerization of Fluoromonomers." Macromolecules 44, no. 7 (April 12, 2011): 2394. http://dx.doi.org/10.1021/ma2003536.

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32

Allen, Michael H., Sean T. Hemp, Adam E. Smith, and Timothy E. Long. "Controlled Radical Polymerization of 4-Vinylimidazole." Macromolecules 45, no. 9 (April 25, 2012): 3669–76. http://dx.doi.org/10.1021/ma300543h.

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33

Ansong, Omari E., Susan Jansen, Yen Wei, Gregory Pomrink, Hui Lu, Alpa Patel, and Shuxi Li. "Accelerated controlled radical polymerization of methacrylates." Polymer International 58, no. 1 (November 18, 2008): 54–65. http://dx.doi.org/10.1002/pi.2492.

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34

Bohrisch, Jörg, Ulrich Wendler, and Werner Jaeger. "Controlled radical polymerization of 4-vinylpyridine." Macromolecular Rapid Communications 18, no. 11 (November 1997): 975–82. http://dx.doi.org/10.1002/marc.1997.030181104.

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35

Charmot, D., P. Corpart, H. Adam, S. Z. Zard, T. Biadatti, and G. Bouhadir. "Controlled radical polymerization in dispersed media." Macromolecular Symposia 150, no. 1 (February 2000): 23–32. http://dx.doi.org/10.1002/1521-3900(200002)150:1<23::aid-masy23>3.0.co;2-e.

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36

Matyjaszewski, Krzysztof. "Environmental aspects of controlled radical polymerization." Macromolecular Symposia 152, no. 1 (March 2000): 29–42. http://dx.doi.org/10.1002/1521-3900(200003)152:1<29::aid-masy29>3.0.co;2-c.

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37

Tamasi, Matthew, Shashank Kosuri, Jason DiStefano, Robert Chapman, and Adam J. Gormley. "Automation of Controlled/Living Radical Polymerization." Advanced Intelligent Systems 2, no. 2 (January 29, 2020): 1900126. http://dx.doi.org/10.1002/aisy.201900126.

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38

Schmidt-Naake, Gudrun, Marco Drache, and Carsten Taube. "TEMPO-controlled free radical suspension polymerization." Die Angewandte Makromolekulare Chemie 265, no. 1 (March 1, 1999): 62–68. http://dx.doi.org/10.1002/(sici)1522-9505(19990301)265:1<62::aid-apmc62>3.0.co;2-p.

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39

Steenbock, M., M. Klapper, and K. Müllen. "“Self-regulation” of controlled radical polymerization." Acta Polymerica 49, no. 7 (July 1998): 376–78. http://dx.doi.org/10.1002/(sici)1521-4044(199807)49:7<376::aid-apol376>3.0.co;2-e.

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40

Jin, Xin, Hongliang Kang, Ruigang Liu, and Yong Huang. "Controlled radical emulsion polymerization of polystyrene." Colloid and Polymer Science 291, no. 10 (June 9, 2013): 2481–85. http://dx.doi.org/10.1007/s00396-013-2998-6.

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41

Kavitha, Amalin A., Anusuya Choudhury, and Nikhil K. Singha. "Controlled Radical Polymerization of Furfuryl Methacrylate." Macromolecular Symposia 240, no. 1 (July 2006): 232–37. http://dx.doi.org/10.1002/masy.200650828.

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42

Özyürek, Zeynep, Hartmut Komber, Stefan Gramm, Dirk Schmaljohann, Axel H. E. Müller, and Brigitte Voit. "Thermoresponsive Glycopolymers via Controlled Radical Polymerization." Macromolecular Chemistry and Physics 208, no. 10 (May 21, 2007): 1035–49. http://dx.doi.org/10.1002/macp.200600661.

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43

Tasdelen, Mehmet Atilla, Mustafa Uygun, and Yusuf Yagci. "Photoinduced Controlled Radical Polymerization in Methanol." Macromolecular Chemistry and Physics 211, no. 21 (September 30, 2010): 2271–75. http://dx.doi.org/10.1002/macp.201000445.

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44

Jenkins, Aubrey D., Richard G. Jones, and Graeme Moad. "Terminology for reversible-deactivation radical polymerization previously called "controlled" radical or "living" radical polymerization (IUPAC Recommendations 2010)." Pure and Applied Chemistry 82, no. 2 (November 18, 2009): 483–91. http://dx.doi.org/10.1351/pac-rep-08-04-03.

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This document defines terms related to modern methods of radical polymerization, in which certain additives react reversibly with the radicals, thus enabling the reactions to take on much of the character of living polymerizations, even though some termination inevitably takes place. In recent technical literature, these reactions have often been loosely referred to as, inter alia, "controlled", "controlled/living", or "living" polymerizations. The use of these terms is discouraged. The use of "controlled" is permitted as long as the type of control is defined at its first occurrence, but the full name that is recommended for these polymerizations is "reversible-deactivation radical polymerization".

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45

Quiclet-Sire, Béatrice, and Samir Z. Zard. "Fun with radicals: Some new perspectives for organic synthesis." Pure and Applied Chemistry 83, no. 3 (October 15, 2010): 519–51. http://dx.doi.org/10.1351/pac-con-10-08-07.

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The degenerative radical addition-transfer of xanthates onto alkenes allows the rapid assembly of richly functionalized structures. Various families of open-chain, cyclic, and polycyclic compounds can thus be readily accessed. Furthermore, the process can be extended to the synthesis or modification of aromatic and heteroaromatic derivatives by exploiting the possibility of using peroxides both as initiators and stoichiometric oxidants. The modification of existing polymers and the controlled synthesis of block polymers by what is now known as the RAFT/MADIX (reversible addition–fragmentation transfer/macromolecular design by interchange of xanthate) process is described briefly.

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46

Yaǧci, Yusuf, Ayşegül Başkan Düz, and Ayşen Önen. "Controlled radical polymerization initiated by stable radical terminated polytetrahydrofuran." Polymer 38, no. 11 (May 1997): 2861–63. http://dx.doi.org/10.1016/s0032-3861(97)85626-1.

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47

Xia, Jianhui, Scott G. Gaynor, and Krzysztof Matyjaszewski. "Controlled/“Living” Radical Polymerization. Atom Transfer Radical Polymerization of Acrylates at Ambient Temperature." Macromolecules 31, no. 17 (August 1998): 5958–59. http://dx.doi.org/10.1021/ma980725b.

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48

Save, Maud, Yohann Guillaneuf, and Robert G. Gilbert. "Controlled Radical Polymerization in Aqueous Dispersed Media." Australian Journal of Chemistry 59, no. 10 (2006): 693. http://dx.doi.org/10.1071/ch06308.

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Controlled radical polymerization (CRP), sometimes also termed ‘living’ radical polymerization, offers the potential to create a wide range of polymer architectures, and its implementation in aqueous dispersed media (e.g. emulsion polymerization, used on a vast scale industrially) opens the way to large-scale manufacture of products based on this technique. Until recently, implementing CRP in aqueous dispersed media was plagued with problems such as loss of ‘living’ character and loss of colloidal stability. This review examines the basic mechanistic processes in free-radical polymerization in aqueous dispersed media (e.g. emulsion polymerization), and then examines, through this mechanistic understanding, the new techniques that have been developed over the last few years to implement CRP successfully in emulsion polymerizations and related processes. The strategies leading to these successes can thus be understood in terms of the various mechanisms which dominate CRP systems in dispersed media; these mechanisms are sometimes quite different from those in conventional free-radical polymerization in these media.

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49

Xue, Wentao, Jie Wang, Ming Wen, Gaojian Chen, and Weidong Zhang. "Integration of CuAAC Polymerization and Controlled Radical Polymerization into Electron Transfer Mediated “Click-Radical” Concurrent Polymerization." Macromolecular Rapid Communications 38, no. 6 (February 3, 2017): 1600733. http://dx.doi.org/10.1002/marc.201600733.

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50

Sütekin, S. Duygu, and Olgun Güven. "Radiation-induced controlled polymerization of acrylic acid by RAFT and RAFT-MADIX methods in protic solvents." Radiation Physics and Chemistry 142 (January 2018): 82–87. http://dx.doi.org/10.1016/j.radphyschem.2017.01.046.

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