Poly(thioacrylate)s: expanding the monomer toolbox of functional polymers

被引:21
作者
Aksakal, Suzan [1 ]
Becer, C. Remzi [1 ]
机构
[1] Queen Mary Univ London, Polymer Chem Lab, Sch Mat Sci & Engn, London E1 4NS, England
关键词
TRANSFER RADICAL POLYMERIZATION; THIOL SIDE CHAINS; ALKYL THIOLACRYLATES; CONDENSATION PRODUCTS; COPOLYMERS; THIOMERS;
D O I
10.1039/c6py01721e
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Radically polymerizable monomers such as acrylates, acrylamides, and styrenes have been investigated because of their corresponding polymers for many years. However, thioacrylates are a forgotten class of monomers and have not been studied for decades. Herein, we present a simple synthetic approach to prepare various thioacrylate monomers as well as their controlled radical polymerization for the first time. Four different thioacrylate (TA) monomers namely, ethyl thioacrylate, phenyl thioacrylate, n-propyl thioacrylate and isopropyl thioacrylate have been polymerized via RAFT polymerization. A trithiocarbonate chain transfer agent was utilized to control the molar mass and dispersity of thioacrylate polymers. Homopolymers of thioacrylates with different degrees of polymerizations were prepared and their block copolymerizations were studied with ethylacrylate and thioacrylates. All obtained polymers were analyzed in detail using GPC, NMR, TGA, DSC and water contact angle.
引用
收藏
页码:7011 / 7018
页数:8
相关论文
共 35 条
[1]   Cu(0)-mediated living radical polymerization: recent highlights and applications; a perspective [J].
Anastasaki, Athina ;
Nikolaou, Vasiliki ;
Haddleton, David M. .
POLYMER CHEMISTRY, 2016, 7 (05) :1002-1026
[2]   Synthesis of poly (2-ethyl-2-oxazoline)-b-poly(styrene) copolymers via a dual initiator route combining cationic ring-opening polymerization and atom transfer radical polymerization [J].
Becer, C. Remzi ;
Paulus, Renzo M. ;
Hoeppener, Stephanie ;
Hoogenboom, Richard ;
Fustin, Charles-Andre ;
Gohy, Jean-Francois ;
Schubert, Ulrich S. .
MACROMOLECULES, 2008, 41 (14) :5210-5215
[3]   Thiomers:: potential excipients for non-invasive peptide delivery systems [J].
Bernkop-Schnürch, A ;
Krauland, AH ;
Leitner, VM ;
Palmberger, T .
EUROPEAN JOURNAL OF PHARMACEUTICS AND BIOPHARMACEUTICS, 2004, 58 (02) :253-263
[4]   Thiomers - From bench to market [J].
Bonengel, Sonja ;
Bernkop-Schnuerch, Andreas .
JOURNAL OF CONTROLLED RELEASE, 2014, 195 :120-129
[5]   Copper-Mediated Living Radical Polymerization (Atom Transfer Radical Polymerization and Copper(0) Mediated Polymerization): From Fundamentals to Bioapplications [J].
Boyer, Cyrille ;
Corrigan, Nathaniel Alan ;
Jung, Kenward ;
Diep Nguyen ;
Thuy-Khanh Nguyen ;
Adnan, Nik Nik M. ;
Oliver, Susan ;
Shanmugam, Sivaprakash ;
Yeow, Jonathan .
CHEMICAL REVIEWS, 2016, 116 (04) :1803-1949
[6]   Functional polymers by atom transfer radical polymerization [J].
Coessens, V ;
Pintauer, T ;
Matyjaszewski, K .
PROGRESS IN POLYMER SCIENCE, 2001, 26 (03) :337-377
[7]   Realisation of siloxane ionomers by mild oxidation of alkylmercaptosiloxanes [J].
Evans, PJ ;
Slade, RCT ;
Varcoe, JR ;
Young, KE .
JOURNAL OF MATERIALS CHEMISTRY, 1999, 9 (12) :3015-3021
[8]   Nitroxide-Mediated Radical Polymerization: Limitations and Versatility [J].
Grubbs, Robert B. .
POLYMER REVIEWS, 2011, 51 (02) :104-137
[9]   SOLUTION PROPERTIES AND CHAIN FLEXIBILITY OF POLY(THIOLMETHACRYLATES) .2. POLY(CYCLOHEXYL THIOLMETHACRYLATE) [J].
HADJICHRISTIDIS, N ;
TOULOUPIS, C ;
FETTERS, LJ .
MACROMOLECULES, 1981, 14 (01) :128-130
[10]  
Hadjichristidis N., 1981, POLYMER, V22, P63