Synthesis and Characterization of Novel Methacrylate Copolymers based on Sulfonamide and Coumarine: Monomer Reactivity Ratios, Biological Activity, Thermal Stability, and Optical Properties

被引:22
作者
Erol, Ibrahim [1 ]
Sanli, Gulay [1 ]
Dilek, Meltem [1 ]
Ozcan, Levent [1 ]
机构
[1] Afyon Kocatepe Univ, Dept Chem, Fac Sci & Arts, Afyon, Turkey
关键词
activation energy; biological activity; biomaterials; coumarin methacrylate; differential scanning calorimetry (DSC); functionalization of polymers; monomer reactivity ratios; radical polymerization; suflonamide methacrylate; PH-SENSITIVE POLYMERS; SIDE-GROUP; TRANSITION; POLYMERIZATION; PHOTOALIGNMENT; DEGRADATION; SYSTEM;
D O I
10.1002/pola.24220
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
The free radical copolymerization of 2-oxo-2-[(4-sulfamoylphenyl) amino]ethyl-2-methylpropenoate (SAEMA) with 4-methyl-2-oxo-2H-chromen-7-yl-2-methylpropenoate (MCMA) has been carried out in 1, 4-dioxane at 65 degrees C +/- 1 degrees C and the copolymers were analyzed by Fourier-transform infrared, H-1-NMR, C-13-NMR and gel permeation chromatography. H-1-NMR and elemental analysis was used to determine the molar fractions of SAEMA and MCMA in the copolymers. The monomer-reactivity ratios were calculated according to the general copolymerization equation using Kelen-Tudos and Fineman-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 MCMA 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. The photochemical properties of the polymers were investigated by UV spectra. (c) 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 4323-4334, 2010
引用
收藏
页码:4323 / 4334
页数:12
相关论文
共 54 条
[1]   In situ quantitative 1H NMR monitoring of monomer consumption:: A simple and fast way of estimating reactivity ratios [J].
Aguilar, MR ;
Gallardo, A ;
Fernández, MD ;
San Román, J .
MACROMOLECULES, 2002, 35 (06) :2036-2041
[2]  
ARSHADY R, 1981, MACROMOL CHEM PHYS, V182, P41
[3]   Studies in chemotherapy. VII. A theory of the relation of structure to activity of sulfanilamide type compounds [J].
Bell, PH ;
Roblin, RO .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1942, 64 :2905-2917
[4]   A very short route to enantiomerically pure coumarin-bearing fluorescent amino acids [J].
Brun, MP ;
Bischoff, L ;
Garbay, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3432-3436
[5]  
CHAN ECZ, 1993, AGAR DIFFUSION METHO, P225
[6]   Thermal properties, specific interactions, and surface energies of PMMA terpolymers having high glass transition temperatures and low moisture absorptions [J].
Chen, JK ;
Kuo, SW ;
Kao, HC ;
Chang, FC .
POLYMER, 2005, 46 (07) :2354-2364
[7]  
Degutis J., 1975, U. S. S. R.-patent, Patent No. 466227
[8]   Synthesis and characterization of cardo-polysulfonates of 1,1'-bis(4-hydroxy phenyl)cyclohexane with 1,3-benzene and 2,4-toluene disulfonyl chlorides [J].
Desai, JA ;
Dayal, U ;
Parsania, PH .
JOURNAL OF MACROMOLECULAR SCIENCE-PURE AND APPLIED CHEMISTRY, 1996, A33 (08) :1113-1122
[9]  
DESILVA MES, 2000, POLYM DEG STABIL, V67, P491
[10]   Synthesis, characterization, and polymerization of new methacrylate esters having pendant amide moieties [J].
Erol, I ;
Soykan, C .
JOURNAL OF MACROMOLECULAR SCIENCE-PURE AND APPLIED CHEMISTRY, 2002, 39 (05) :405-417