Synthesis, characterization, thermal properties, and antimicrobial activity of 4‐chloro‐3‐methyl phenyl methacrylate/8‐quinolinyl methacrylate copolymers

Abstract

4‐Chloro‐3‐methyl phenyl methacrylate (CMPM) and 8‐quinolinyl methacrylate (8‐QMA) were synthesized through the reaction of 4‐chloro‐3‐methyl phenol and 8‐hydroxy quinoline, respectively, with methacryloyl chloride. The homopolymers and copolymers were prepared by free‐radical polymerization with azobisisobutyronitrile as the initiator at 70 °C. Copolymers of CMPM and 8‐QMA of different compositions were prepared. The monomers were characterized with IR spectroscopy and 1H NMR techniques. The copolymers were characterized with IR spectroscopy. UV spectroscopy was used to obtain the compositions of the copolymers. The monomer reactivity ratios were calculated with the Fineman–Ross method. The molecular weights and polydispersity values of the copolymers were determined with gel permeation chromatography. The thermal stability of the polymers was evaluated with thermogravimetric analysis under a nitrogen atmosphere. The homopolymers and copolymers were tested for their antimicrobial activity againstbacteria, fungi, and yeast. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 157–167, 2005

Synthesis, exchange reactions, and biological activity of poly(8‐methacryloxyquinoline)

“…The yields of the recrystallized products usually ranged from 70 to 85% (mp = 50–52°C, lit. 49°C) 22…”

Perfluorocyclobutyl-based methacrylate monomers: Synthesis and radical polymerization

“…Therefore, another approach of demethylation using BBr 3 was employed in CH 2 Cl 2 at room temperature [17,18], which gave PFCB-containing phenols with almost quantitative yields. The esterification of PFCB-containing phenols and methacryloyl chloride was carried out following previously reported procedure [21] with a yield about 70%. Chemical structure of PFCB-containing methacrylate monomers was confirmed by 1 H NMR, 19 F NMR, 13 C NMR, FT-IR and HRMS.…”

Synthesis, Characterization and Antimicrobial Activity of Novel Acrylic Copolymers

“…Although the chlorine content of polymers appeared to be most important for imparting antimicrobial properties, it is to be noted that other moieties also possess antimicrobial activity. The copolymers of CMPM with 8-Quinolinyl methacrylate 17 are more potent antimicrobial agents than the copolymers of CMPM and MMA. It thus appears that 8-Quinoline moiety also might have some role to enhance antimicrobial activity.…”

“…The details of experimental procedure have been reported elsewhere. 17,19 RESULTS AND DISCUSSION Five copolymers of CMPM with MMA were synthesized by taking different mole fraction of the monomers in the feed ranging from 0.2 to 0.8 (Table I). In order to satisfy the differential copolymerization equation, the reaction time was so selected as to have less than 10 wt % conversion.…”

“…Narsinhaswamy 16 et al proposed a method for the determination of copolymer composition in the copolymer of phenyl methacrylate and glycidyl methacrylate from 1 H NMR data. In continuous to our work on copolymers of CMPM and 8-Quinolinyl methacrylate, 17 it was thought appropriate to synthesize copolymers of CMPM with MMA and examine their bioactivity. This investigation will help to understand the role of moieties other than chlorine in imparting antimicrobial activity to a polymer.…”