Nitroxide-Mediated Controlled Radical Copolymerization of α-Trifluoromethylstyrenes with Styrenes

Fluorinated polymers are important materials in everyday life; however, most monomers of widely used fluoropolymers are gaseous, and their polymerization is difficult in an ordinary laboratory. Therefore, partially fluorinated polymers have recently been reported. As an easy-to-handle fluorine-conta...

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Main Authors: Tadashi Kanbara, Yuriko Ito, Airi Yamaguchi, Tomoko Yajima
Format: Article
Language:English
Published: MDPI AG 2024-03-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/29/6/1214
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author Tadashi Kanbara
Yuriko Ito
Airi Yamaguchi
Tomoko Yajima
author_facet Tadashi Kanbara
Yuriko Ito
Airi Yamaguchi
Tomoko Yajima
author_sort Tadashi Kanbara
collection DOAJ
description Fluorinated polymers are important materials in everyday life; however, most monomers of widely used fluoropolymers are gaseous, and their polymerization is difficult in an ordinary laboratory. Therefore, partially fluorinated polymers have recently been reported. As an easy-to-handle fluorine-containing monomer, α-trifluoromethylstyrene (TFMST) can be used to produce partially fluorinated polymers with trifluoromethyl groups in the main chain; however, TFMST does not homopolymerize, and there are limited reports on its copolymerization with styrene (ST). In this study, we applied the controlled radical polymerization method, which is effective for the polymerization of ST, to the copolymerization of TFMST and ST. We also showed that nitroxide-mediated polymerization is effective. The content ratio of TFMST in the TFMST–ST copolymer can be controlled between 10% and 40% by changing its monomer ratio. Additionally, the polymerization of TFMST and ST with substituents was performed to increase structural variations. The thermal stability as well as water and oil repellency of the synthesized polymers with different composition ratios and substituents were also evaluated.
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spelling doaj.art-7312b6d4035d449bac8fc9688bef053f2024-03-27T13:56:45ZengMDPI AGMolecules1420-30492024-03-01296121410.3390/molecules29061214Nitroxide-Mediated Controlled Radical Copolymerization of α-Trifluoromethylstyrenes with StyrenesTadashi Kanbara0Yuriko Ito1Airi Yamaguchi2Tomoko Yajima3Department of Chemistry, Ochanomizu University, 2-1-1 Otsuka, Bukyo-ku, Tokyo 104-8610, JapanDepartment of Chemistry, Ochanomizu University, 2-1-1 Otsuka, Bukyo-ku, Tokyo 104-8610, JapanDepartment of Chemistry, Ochanomizu University, 2-1-1 Otsuka, Bukyo-ku, Tokyo 104-8610, JapanDepartment of Chemistry, Ochanomizu University, 2-1-1 Otsuka, Bukyo-ku, Tokyo 104-8610, JapanFluorinated polymers are important materials in everyday life; however, most monomers of widely used fluoropolymers are gaseous, and their polymerization is difficult in an ordinary laboratory. Therefore, partially fluorinated polymers have recently been reported. As an easy-to-handle fluorine-containing monomer, α-trifluoromethylstyrene (TFMST) can be used to produce partially fluorinated polymers with trifluoromethyl groups in the main chain; however, TFMST does not homopolymerize, and there are limited reports on its copolymerization with styrene (ST). In this study, we applied the controlled radical polymerization method, which is effective for the polymerization of ST, to the copolymerization of TFMST and ST. We also showed that nitroxide-mediated polymerization is effective. The content ratio of TFMST in the TFMST–ST copolymer can be controlled between 10% and 40% by changing its monomer ratio. Additionally, the polymerization of TFMST and ST with substituents was performed to increase structural variations. The thermal stability as well as water and oil repellency of the synthesized polymers with different composition ratios and substituents were also evaluated.https://www.mdpi.com/1420-3049/29/6/1214fluorine-containing polymersnitroxide-mediated polymerizationcontrolled polymerization
spellingShingle Tadashi Kanbara
Yuriko Ito
Airi Yamaguchi
Tomoko Yajima
Nitroxide-Mediated Controlled Radical Copolymerization of α-Trifluoromethylstyrenes with Styrenes
Molecules
fluorine-containing polymers
nitroxide-mediated polymerization
controlled polymerization
title Nitroxide-Mediated Controlled Radical Copolymerization of α-Trifluoromethylstyrenes with Styrenes
title_full Nitroxide-Mediated Controlled Radical Copolymerization of α-Trifluoromethylstyrenes with Styrenes
title_fullStr Nitroxide-Mediated Controlled Radical Copolymerization of α-Trifluoromethylstyrenes with Styrenes
title_full_unstemmed Nitroxide-Mediated Controlled Radical Copolymerization of α-Trifluoromethylstyrenes with Styrenes
title_short Nitroxide-Mediated Controlled Radical Copolymerization of α-Trifluoromethylstyrenes with Styrenes
title_sort nitroxide mediated controlled radical copolymerization of α trifluoromethylstyrenes with styrenes
topic fluorine-containing polymers
nitroxide-mediated polymerization
controlled polymerization
url https://www.mdpi.com/1420-3049/29/6/1214
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AT yurikoito nitroxidemediatedcontrolledradicalcopolymerizationofatrifluoromethylstyreneswithstyrenes
AT airiyamaguchi nitroxidemediatedcontrolledradicalcopolymerizationofatrifluoromethylstyreneswithstyrenes
AT tomokoyajima nitroxidemediatedcontrolledradicalcopolymerizationofatrifluoromethylstyreneswithstyrenes