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Journal articles on the topic 'Living radical polymerization'

Author: Grafiati

Published: 4 June 2021

Last updated: 4 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

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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3

YAMAGO, Shigeru, and Yasuyuki NAKAMURA. "Living Radical Polymerization: 4. Stereospecific Living Radical Polymerization." NIPPON GOMU KYOKAISHI 83, no. 2 (2010): 35–39. http://dx.doi.org/10.2324/gomu.83.35.

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4

Yamago, S., and Y. Nakamura. "Living Radical Polymerization 4. Stereospecific Living Radical Polymerization." International Polymer Science and Technology 37, no. 6 (June 2010): 51–56. http://dx.doi.org/10.1177/0307174x1003700614.

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5

YAMADA, Takeshi, Kazunori IIDA, and Shigeru YAMAGO. "Living Radical Polymerization." KOBUNSHI RONBUNSHU 64, no. 6 (2007): 329–42. http://dx.doi.org/10.1295/koron.64.329.

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6

Masuda, Tsukuru, and Masamichi Nakayama. "Living radical polymerization." Drug Delivery System 36, no. 1 (January 25, 2021): 68–71. http://dx.doi.org/10.2745/dds.36.68.

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7

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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8

KAMIGAITO, Masami, and Kotaro SATOH. "Stereospecific Living Radical Polymerization." Kobunshi 55, no. 4 (2006): 250–53. http://dx.doi.org/10.1295/kobunshi.55.250.

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9

Moad, Graeme, Ezio Rizzardo, and San H. Thang. "Toward Living Radical Polymerization." Accounts of Chemical Research 41, no. 9 (September 16, 2008): 1133–42. http://dx.doi.org/10.1021/ar800075n.

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10

YAMADA, Bunichiro. "Living Free-radical Polymerization." Kobunshi 45, no. 9 (1996): 676–81. http://dx.doi.org/10.1295/kobunshi.45.676.

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11

Matyjaszewski, Krzysztof. "From "Living" Carbocationic to "Living" Radical Polymerization." Journal of Macromolecular Science, Part A 31, no. 8 (1994): 989–1000. http://dx.doi.org/10.1080/10601329408545697.

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12

Matyjaszewski, Krzysztof. "From “Living” Carbocationic to “Living” Radical Polymerization." Journal of Macromolecular Science, Part A 31, no. 8 (August 1994): 989–1000. http://dx.doi.org/10.1080/10601329409349774.

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13

Goto, Atsushi, and Takeshi Fukuda. "Kinetics of living radical polymerization." Progress in Polymer Science 29, no. 4 (April 2004): 329–85. http://dx.doi.org/10.1016/j.progpolymsci.2004.01.002.

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14

McQuillan, B. W., and S. Paguio. "Living Radical Polymerization of Trimethylsilylstyrene." Fusion Technology 38, no. 1 (July 2000): 108–9. http://dx.doi.org/10.13182/fst00-a36124.

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15

YAMAGO, Shigeru. "Living Radical Polymerization under Photoimadiation." Journal of The Adhesion Society of Japan 53, no. 5 (May 1, 2017): 157–63. http://dx.doi.org/10.11618/adhesion.53.157.

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16

Kamigaito, Masami, Tsuyoshi Ando, and Mitsuo Sawamoto. "Metal-Catalyzed Living Radical Polymerization." Chemical Reviews 101, no. 12 (December 2001): 3689–746. http://dx.doi.org/10.1021/cr9901182.

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17

Zheng, Xuefeng, Miao Yue, Peng Yang, Qi Li, and Wantai Yang. "Cycloketyl radical mediated living polymerization." Polymer Chemistry 3, no. 8 (2012): 1982. http://dx.doi.org/10.1039/c2py20117h.

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18

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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19

Kamigaito, Masami, and Kotaro Satoh. "Stereoregulation in Living Radical Polymerization." Macromolecules 41, no. 2 (January 2008): 269–76. http://dx.doi.org/10.1021/ma071499l.

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20

Keoshkerian, Barkev, Michael K. Georges, and Danielle Boils-Boissier. "Living Free-Radical Aqueous Polymerization." Macromolecules 28, no. 18 (August 1995): 6381–82. http://dx.doi.org/10.1021/ma00122a058.

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21

Catala, J. M., F. Bubel, and S. Oulad Hammouch. "Living Radical Polymerization: Kinetic Results." Macromolecules 28, no. 24 (November 1995): 8441–43. http://dx.doi.org/10.1021/ma00128a069.

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22

Geng, Jin, Weishuo Li, Yichuan Zhang, Neelima Thottappillil, Jessica Clavadetscher, Annamaria Lilienkampf, and Mark Bradley. "Radical polymerization inside living cells." Nature Chemistry 11, no. 6 (April 15, 2019): 578–86. http://dx.doi.org/10.1038/s41557-019-0240-y.

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23

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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24

Matyjaszewski, Krzysztof. "Transformation of “living” carbocationic and other polymerizations to controlled/“living” radical polymerization." Macromolecular Symposia 132, no. 1 (July 1998): 85–101. http://dx.doi.org/10.1002/masy.19981320111.

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25

Theis, Alexander, Martina H. Stenzel, Thomas P. Davis, Michelle L. Coote, and Christopher Barner-Kowollik. "A Synthetic Approach to a Novel Class of Fluorine-Bearing Reversible Addition - Fragmentation Chain Transfer (RAFT) Agents: F-RAFT." Australian Journal of Chemistry 58, no. 6 (2005): 437. http://dx.doi.org/10.1071/ch05069.

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A synthetic route is described to a novel class of reversible addition–fragmentation chain transfer (RAFT) agents bearing a fluorine Z-group. Such F-RAFT agents are theoretically predicted to allow living free radical polymerization of various monomers without affecting the rate of polymerization, and should also facilitate the construction of block copolymers from monomers with disparate reactivity. The class of F-RAFT agents is exemplified by the example of benzyl fluoro dithioformate (BFDF) in styrene free-radical polymerizations and the process is shown to induce living polymerization.

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26

Xu, Yuan Qing, Xiao Min Fang, Tao Ding, and Yan Rong Ren. "Living Radical Polymerizations of Methyl Methacrylate Mediated by Tris-(4-Carboxyphenyl) Methane." Advanced Materials Research 631-632 (January 2013): 3–8. http://dx.doi.org/10.4028/www.scientific.net/amr.631-632.3.

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Pseudo-living radical polymerization and reverse atom transfer radical polymerization (RATRP) of methyl methacrylate (MMA) were reported, utilizing tris-(4-carboxyphenyl)methane (TCOPM) as the thermal iniferter and initiator, respectively. The polymerization of MMA using TCOPM as thermal iniferter possesses pseudo-living characteristics: Mn increases with conversion in a certain range, and the resulted polymer can be used as the macro-initiator for chain extension. The RATRP using TCOPM as the initiator shows linear kinetic plot, linear increase of Mn with conversion and narrow polydispersity indice (PDI) of the resultant polymers. Effects of temperature on both polymerizations were investigated.

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27

Fischer, Hanns. "The Persistent Radical Effect In “Living” Radical Polymerization." Macromolecules 30, no. 19 (September 1997): 5666–72. http://dx.doi.org/10.1021/ma970535l.

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28

Matyjaszewski, Krzysztof, Takeo Shigemoto, Jean M. J. Fréchet, and Marc Leduc. "Controlled/“Living” Radical Polymerization with Dendrimers Containing Stable Radicals." Macromolecules 29, no. 12 (January 1996): 4167–71. http://dx.doi.org/10.1021/ma9600163.

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29

FUKUDA, Takeshi. "Kinetic Characterization of Living Radical Polymerization." Kobunshi 48, no. 7 (1999): 498–501. http://dx.doi.org/10.1295/kobunshi.48.498.

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30

Butté, Alessandro, Giuseppe Storti, and Massimo Morbidelli. "Kinetics of “living” free radical polymerization." Chemical Engineering Science 54, no. 15-16 (July 1999): 3225–31. http://dx.doi.org/10.1016/s0009-2509(98)00369-8.

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31

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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32

Korolev, G. V., and A. P. Marchenko. "ChemInform Abstract: “Living”-Chain Radical Polymerization." ChemInform 31, no. 45 (November 7, 2000): no. http://dx.doi.org/10.1002/chin.200045299.

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33

Boutevin, B. "From telomerization to living radical polymerization." Journal of Polymer Science Part A: Polymer Chemistry 38, no. 18 (2000): 3235–43. http://dx.doi.org/10.1002/1099-0518(20000915)38:18<3235::aid-pola20>3.0.co;2-6.

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34

Otsu, Takayuki. "Iniferter concept and living radical polymerization." Journal of Polymer Science Part A: Polymer Chemistry 38, no. 12 (June 15, 2000): 2121–36. http://dx.doi.org/10.1002/(sici)1099-0518(20000615)38:12<2121::aid-pola10>3.0.co;2-x.

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35

Mardare, Daniela, and Krzysztof Matyjaszewski. ""Living" radical polymerization of vinyl acetate." Macromolecules 27, no. 3 (May 1994): 645–49. http://dx.doi.org/10.1021/ma00081a003.

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36

Bisht, Harender Singh, and Alok Kumar Chatterjee. "LIVING FREE-RADICAL POLYMERIZATION—A REVIEW." Journal of Macromolecular Science, Part C: Polymer Reviews 41, no. 3 (July 31, 2001): 139–73. http://dx.doi.org/10.1081/mc-100107774.

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37

Yan, Deyue, Hong Jiang, and Xunpei Fan. "Kinetic model of living radical polymerization." Macromolecular Theory and Simulations 5, no. 2 (March 1996): 333–45. http://dx.doi.org/10.1002/mats.1996.040050213.

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38

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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39

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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40

YAMAGO, Shigeru, and Yasuyuki NAKAMURA. "Living Radical Polymerization: 1. Polymerization Mechanism and Methods: 1." NIPPON GOMU KYOKAISHI 82, no. 3 (2009): 135–40. http://dx.doi.org/10.2324/gomu.82.135.

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41

YAMAGO, Shigeru, and Yasuyuki NAKAMURA. "Living Radical Polymerization: 2. Polymerization Mechanism and Methods: 2." NIPPON GOMU KYOKAISHI 82, no. 8 (2009): 363–69. http://dx.doi.org/10.2324/gomu.82.363.

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42

Monteiro, M. J., R. Bussels, S. Beuermann, and M. Buback. "High Pressure 'Living' Free-Radical Polymerization of Styrene in the Presence of RAFT." Australian Journal of Chemistry 55, no. 7 (2002): 433. http://dx.doi.org/10.1071/ch02079.

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Reversible addition-fragmentation chain transfer (RAFT) polymerization of styrene was studied at high pressure, employing two dithioester RAFT agents with an isopropylcyano (5) and a cumyl (6) leaving group, respectively. The high-pressure reaction resulted in low polydispersity polymer. It was found that controlled polymerizations can be performed at increased pressures with a high degree of monomer conversion, which signifies that high-pressure polymerizations can be utilized for the production of higher molecular weight polystyrene of controlled microstructure. Retardation of styrene polymerization was also observed at high pressure in the presence of RAFT agents (5) and (6). It is postulated that the retarding potential of these two RAFT agents is associated with an intermediate radical termination mechanism. High-pressure free-radical polymerizations open the way to producing living polymers with high rates, and thus lower impurities such as 'dead' polymer that are formed through bimolecular termination reactions.

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43

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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44

Fukuda, Takeshi, and Tomoya Terauchi. "Mechanism of “Living” Radical Polymerization Mediated by Stable Nitroxyl Radicals." Chemistry Letters 25, no. 4 (April 1996): 293–94. http://dx.doi.org/10.1246/cl.1996.293.

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45

Aoki, Daisuke, Moeko Yanagisawa, and Hideyuki Otsuka. "Synthesis of well-defined mechanochromic polymers based on a radical-type mechanochromophore by RAFT polymerization: living radical polymerization from a polymerization inhibitor." Polymer Chemistry 11, no. 26 (2020): 4290–96. http://dx.doi.org/10.1039/d0py00590h.

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46

Braun, Dietrich. "Origins and Development of Initiation of Free Radical Polymerization Processes." International Journal of Polymer Science 2009 (2009): 1–10. http://dx.doi.org/10.1155/2009/893234.

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At present worldwide about 45% of the manufactured plastic materials and 40% of synthetic rubber are obtained by free radical polymerization processes. The first free radically synthesized polymers were produced between 1910 and 1930 by initiation with peroxy compounds. In the 1940s the polymerization by redox processes was found independently and simultaneously at IG Farben in Germany and ICI in Great Britain. In the 1950s the systematic investigation of azo compounds as free radical initiators followed. Compounds with labile C–C-bonds were investigated as initiators only in the period from the end of the 1960s until the early 1980s. At about the same time, iniferters with cleavable S–S-bonds were studied in detail. Both these initiator classes can be designated as predecessors for “living” or controlled free radical polymerizations with nitroxyl-mediated polymerizations, reversible addition fragmentation chain transfer processes (RAFT), and atom transfer radical polymerizations (ATRP).

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47

Stenzel, Martina H., and Christopher Barner-Kowollik. "The living dead – common misconceptions about reversible deactivation radical polymerization." Materials Horizons 3, no. 6 (2016): 471–77. http://dx.doi.org/10.1039/c6mh00265j.

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We illustrate common misconceptions and errors when interpreting polymerization data from ‘Living/controlled’ radical polymerization, preferably termed ‘reversible deactivation radical polymerization’ (RDRP). Avoiding the discussed errors leads to better defined materials for soft matter materials applications.

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48

Lei, Lin, Miho Tanishima, Atsushi Goto, and Hironori Kaji. "Living Radical Polymerization via Organic Superbase Catalysis." Polymers 6, no. 3 (March 17, 2014): 860–72. http://dx.doi.org/10.3390/polym6030860.

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49

FUKUDA, Takeshi, and Atsushi GOTO. "Living Radical Polymerization and New Block Copolymers." NIPPON GOMU KYOKAISHI 76, no. 8 (2003): 289–93. http://dx.doi.org/10.2324/gomu.76.289.

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50

YAMAGO, Shigeru. "Living Radical Polymerization Mediated by Organoheteroatom Compounds." Kobunshi 55, no. 4 (2006): 254–57. http://dx.doi.org/10.1295/kobunshi.55.254.

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