Copolymers of 4‐(1‐methyl‐1‐mesityl‐3‐cyclobutyl)‐2‐N‐1, 3‐thiazole‐2‐yl methacrylamide with 2‐[(5‐methylisoxazol‐3‐yl) amino]‐2‐oxo‐ethyl methacrylate: Synthesis, characterization, monomer reactivity ratios and biological activity

Abstract

The free radical copolymerization of 4‐(1‐methyl‐1‐mesityl‐3‐cyclobutyl)‐2‐N‐1, 3‐thiazole‐2‐yl methacrylamide (MCTMA) with 2‐[(5‐methylisoxazol‐3‐yl)amino]‐2‐oxo‐ethyl methacrylate (IAOEMA) has been carried out in 1, 4‐dioxane at 65 °C ± 1 and were analyzed by Fourier transform infrared, 1H NMR, 13C NMR, and gel permeation chromatography. 1H‐NMR analysis was used to determine the molar fractions of MCTMA and IAOEMA in the copolymers. The monomer‐reactivity ratios were calculated according to the general copolymerization equation using Kelen–Tüdõs and Finemann–Ross linearization methods. The reactivity ratios indicated a tendency toward random copolymerization. The polydispersity indices of the polymers, determined with gel permeation chromatography, suggested a strong tendency for chain termination by disproportionation. The thermal behaviors of copolymers with various compositions were investigated by differential scanning calorimetry and thermogravimetric analysis. The glass‐transition temperature of the copolymers increased with increasing MCTMA content in the copolymers. Also, the apparent thermal decomposition activation energies were calculated by the Ozawa method with a Shimadzu TGA 60 thermogravimetric analysis thermobalance. All the products showed moderate activity against different strains of bacteria and fungi. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 530–542, 2008

Synthesis of novel functionalized methacrylate copolymers and their copolymerization kinetics, thermal stability, and biocidal properties

“…(MBAOM) is a new methacrylate bearing the methoxy‐substituted thiazole group on the side branch. In our previous studies, 20,21 methacrylamide monomers with thiazole side groups were synthesized. However, as far as we know, a methacrylate monomer bearing a methoxy‐substituted thiazole group does not exist in the literature.…”

Controlled Synthesis of Thiazole-Based Polymers and Block Copolymers by RAFT Polymerization of Azolyl S-Vinyl Sulfides and Metal Complexation

“…In particular, thiazole is a widely used electron-accepting heterocycle due to the electron-withdrawing nitrogen in the imine (CN) function; consequently, various thiazole-based molecules have been introduced into organic semiconductors . A wide variety of polymers containing thiazole, thiadiazole, and benzothiazole moieties in the side chains have been synthesized by conventional radical − and controlled radical polymerizations. − For example, Schubert et al recently reported the controlled syntheses of methacrylate-based copolymers containing donor–acceptor thiazole dyes, polystyrenes, and polymethacrylates containing thiazole-based, blue-emitting side-chains by reversible addition–fragmentation chain transfer (RAFT) polymerization. They also demonstrated the RAFT syntheses and investigated the energy transfer systems of polymethacrylates composed of thiazole-based chromophores and Os­(II) metal complexes and a statistical terpolymer containing a thiazole-based donor and an acceptor-type chromophore derived from Ru complex .…”

“…Atom transfer radical polymerization was also used for the production of well-defined polymethacrylates with pendant π-conjugated benzothiazole and triblock copolymers composed of thiadiazole-containing oligoester . Conventional radical polymerizations of acrylamides containing benzothiazole units were used to develop fluorescent polymers involving an intramolecular proton transfer. , Other examples involve the syntheses, by conventional radical polymerization, of antimicrobial polymethacrylates based on quaternized thiazole and triazole side-chain groups, biologically active copolymers composed of thiazole-containing methacrylamide and oxazole-containing methacrylate, and an antimicrobial polymethacrylate with pendant thiadiazole units . Because of scientific and industrial interest, several investigations have been made on thiazole-based polymer–metal complexes, which include thiazole-based polymethacrylamide-Cu­(II) complexes having biological activity and thiazole-based copolymer–metal (Ni 2+ and Nd 3+ ) complexes having characteristic magnetic properties …”