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Synthesis, Characterization and Antimicrobial Activity of Novel Acrylic Copolymers

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Synthesis, Characterization and Antimicrobial Activity of Novel Acrylic Copolymers Polymer Journal, Vol. 38, No. 2, pp. 159–170 (2006) Synthesis, Characterization and Antimicrobial Activity of Novel Acrylic Copolymers y Mitul B. DOLIA, Umesh S. PATEL, Arabinda RAY, and Rajni M. PATEL Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar-388120, Gujarat India (Received May 30, 2005; Accepted October 10, 2005; Published February 15, 2006) ABSTRACT: Copolymers of monomers 4-chloro-3-methyl phenyl methacrylate (CMPM) and methyl methacrylate (MMA) were synthesized with different monomer feed ratios using 2,20-azobisisobutyronitrile (AIBN) as initiator in toluene at 70 C. The copolymers were characterized by IR-spectroscopy and their compositions were determined by ultraviolet (UV) and 1H NMR spectroscopy. The linearization method of Fineman–Ross and Kelen–Tudos were employed to calculate the monomer reactivity ratio. Average molecular weight and polydispersity index were obtained by gel permeation chromatography (GPC). Thermogravimetric analysis (TGA and DTA) of copolymers were carried out under a nitrogen atmosphere. Antimicrobial effects of the homo and copolymers were also investigated for various microorganisms such as bacteria, fungi and yeast. [DOI 10.1295/polymj.38.159] KEY WORDS Antimicrobial Activity / Copolymerization / Reactivity Ratio / Thermal Properties / Gel Permeation Chromatography (GPC) / Many polymers with reactive functional groups are and they offer information about the relative reactivity now being synthesized, tested and used not only for of monomer pairs. Many reports have been published their macromolecular properties but also for the prop- on the correlation between the reactivity ratio of vinyl erties of functional groups. These groups provide an monomers and extent of radical polymerization and approach to a subsequent modification of the polymer copolymerizations.14,15 The distribution of protons in for specific end applications.1 Acrylic and methacrylic the two units is an important means of distinguishing esters are readily polymerized or copolymerized with monomers in the copolymerization. The aliphatic pro- a wide range of other monomers. The copolymers of tons of both the monomers are almost indistinguisha- acrylic and methacrylic esters have found use in var- ble. Narsinhaswamy16 et al. proposed a method for the ious applications.2–4 Due to their varied applications, determination of copolymer composition in the co- chlorine containing phenyl methacrylate and its poly- polymer of phenyl methacrylate and glycidyl meth- mers have received considerable attention in recent acrylate from 1H NMR data. years.5,6 These chemicals find application as biocides In continuous to our work on copolymers of CMPM also. Many chlorine containing polymers possessing and 8-Quinolinyl methacrylate,17 it was thought ap- antimicrobial property have been reported.7,8 Phenyl propriate to synthesize copolymers of CMPM with acrylate polymer are relatively newly developed mate- MMA and examine their bioactivity. This investiga- rials compared to the commercial polymers such as vi- tion will help to understand the role of moieties other nylic, acryl amides, alkyl acrylates etc. Phenyl acry- than chlorine in imparting antimicrobial activity to a lates are considered as reactive monomers primarily polymer. We report here the synthesis and character- because of the presence of the aromatic ring.9 The co- ization of monomers CMPM and MMA, their homo polymers of phenyl acrylate and methacrylate exhibit polymers and copolymers using different feed ratio. good adhesive characteristics.10 Incorporation of pho- The copolymer composition was obtained by UV tosensitive group is expected to enhance the usage of and 1H NMR data. The reactivity ratio of monomers methyl methacrylate copolymers in microlithography was obtained by Fineman–Ross and Kelen–Tudos due to improvement in the mechanical properties method. Molecular weight was determined by gel per- without affecting thermal performance.11 meation chromatography. The monomer and polymers Erol and coworkers have prepared new methacry- were characterized from their IR data. The results of late monomers, their derivatives and polymers. These thermal analysis on polymers are also included in this authors have also investigated biological activity of paper. Homo and copolymers were also tested for these polymers and they showed good biological ac- their antimicrobial properties against microorganisms tivity.12,13 such as bacteria (Bacillus subtilis, Escherichia coli Reactivity ratios are among the most important pa- and Staphylococcus citreus), fungi (Aspergillus niger, rameters for determination of copolymer composition Sporotichum pulverulentum and Trichoderma ligno- yTo whom correspondence should be addressed (Tel: +91-2692-226855, E-mail: [email protected]). 159 M. B. DOLIA et al. rum) and yeast (Candida utilis, Saccharomyces cere- 2925 ({CH3 ), 1743 (C=O), 1642 (C=C), 1232 visiae and Pichia stipitis). (asymmetric C{O{C) and 1160 (symmetric C{O{C), 980 (–CH bending mode of vinyl group), 720 (rocking EXPERIMENTAL mode of vinyl group), 670 (C{Cl), 1590 and 1488 (bands due to phenyl ring). Materials 4-chloro-3-methyl phenol and methyl methacrylate 1H NMR ( ppm) (60 MHz) Data of Monomer CMPM (S.D. fine chemicals), 2,20-azobisisobutyronitrile The NMR spectrum of CMPM is shown in Figure (AIBN, Aldrich), methacrylic acid and benzoyl chlo- 2b. The resonances are: ride (chiti chem.) have been used without any further 1H NMR ( ppm) (60 MHz): 2.275 (6H) (methyl purification. Solvents were purified by fractional dis- protons), 6.494 (1H) and 6.533 (1H) (non-equivalent tillation. methylene protons), 7.080–7.217 (3H) (aromatic pro- tons). Synthesis of Methacryloyl Chloride Methacryloyl chloride was prepared following the Copolymerization standard procedure given by Stempel.18 Copolymers of CMPM with MMA having different feed composition were synthesized by free radical Synthesis of 4-Chloro-3-methyl Phenyl Methacrylate polymerization in toluene using AIBN as free radical (CMPM) initiator. The feed composition of both the monomer The esterification was performed with methacryloyl and comonomer is given in Table I. Appropriate chloride and 4-chloro-3-methyl phenol (CMP). Abso- quantities of monomer, comonomer, toluene (10 mL), lute alcohol (400 mL) and NaOH (0.2 mol, 8.0 g) were and AIBN (0.5% of total monomers) were mixed in a added to a three necked flask, equipped with a stirrer, round bottom flask equipped with mechanical stirrer condenser and thermometer. The flask was placed in a and reflux condenser. The reaction mixture was heated water bath. The contents of the flask were stirred until to 70 C for 5 h with stirring. It was then cooled to all the NaOH dissolved. CMP (0.2 mol, 42.1 g) was room temperature and the resulting polymer solution added to this. The reaction mixture was heated to was slowly poured in a large volume of methanol with 60 C for 30 min with stirring, cooled to room temper- stirring, when the polymer precipitated out. It was ature and then to 0–5 C by ice. Freshly prepared then filtered and washed with methanol. Solid poly- methacryloyl chloride (0.21 mol, 20.5 mL) was added mers were purified by repeated precipitation by meth- drop wise within 60 min to the cooled reaction mix- anol from solution in DMF and finally dried. Reaction ture. The reaction temperature (0–5 C) was main- scheme (Figure 1) shows the reaction leading to the tained through out the addition. It was then stirred formation of homopolymer as well as copolymers of for 90 min and poured into crushed ice-water mixture, CMPM with MMA. The yield of copolymers varies where a light yellow color liquid product settled from 80 to 89%. down. That was extracted with ether. The lower aqueous layer is separated. The remaining solution Characterization of Polymers is transferred to a petry dish to allow evaporation of Infrared spectra of solid samples in KBr pellets ether at room temperature and then dried over anhy- were recorded with a NICOLET-400D FT IR spec- drous calcium chloride in vacuum desicator. The boil- trophotometer. Shimadzu-160-A recording UV–vis ing point of this monomer was found to be 230 C. spectrophotometer was used to determine copolymer Yield 75%. composition and reactivity ratios. HITACHI-R-1500 FT NMR spectrophotometer (60 MHz) was also used Characterization of Monomers CMPM to determine copolymer composition. Molecular The monomer was characterized by FT IR and weights of the polymers were obtained by gel perme- 1H NMR spectroscopy. IR spectra of monomer was ation chromatography (Waters 600 E) equipped with a recorded using NICOLET 400D FT IR spectrophotom- 410-RI detectors calibrated with polystyrene stand- eter. 1H NMR spectra of monomer was recorded on ards. Thermogravimetic analysis was performed with HITACHI-R-1500 FT NMR spectrophotometer (60 Du Pont-951 thermal analyzer at a heating rate of MHz) using CDCl3 as solvent and tetramethylsilane 10 C/min in nitrogen atmosphere. Differential ther- as an internal standard. mal analysis (DTA) traces were obtained with Du Pont-9900 differential thermal analyzer at a heating IR Data of Monomer CMPM rate of 10 C/min in nitrogen atmosphere. A heating The IR spectrum of monomer CMPM is shown in rate of 10 C/min and a sample size of 10 Æ 1 mg Figure 2a. The important absorptions in cmÀ1 are: were used in each experiment. Intrinsic viscosity 160 Polym. J., Vol. 38, No. 2, 2006 Synthesis, Characterization, and Antimicrobial Activity Table I. Copolymer composition and reactivity ratios of copolymers of CMPM and MMA Monomer feed Composition Reactivity ratio Sample composition Conversion of CMPM M m F2 Fðf À 1Þ G H code CMPM MMA F ¼ 1 f ¼ 1 H ¼ G ¼ ¼ ¼ (%) in the copolymer M2 m2 f f þ H þ H no. [M1][M2] F–R K–T [m1] (mole) (mole) M-1 1.0 — — — r1 r2 r1 r2 M-2 0.2 0.8 8.72 (0.246)Ã, 0.225 0.25 0.290 0.216 À0:612 À0:493 0.174 M-3 0.4 0.6 9.12 (0.375)Ã, 0.389 0.67 0.636 0.706 À0:383 À0:221 0.408 M-4 0.5 0.5 8.83 (0.483)Ã, 0.468 1.0 0.88 1.136 À0:136 À0:063 0.526 0.75 0.88 0.70 0.82 M-5 0.6 0.4 7.86 (0.571)Ã, 0.573 1.5 1.342 1.677 0.382 0.142 0.621 M-6 0.8 0.2 8.42 (0.775)Ã, 0.767 4.0 3.292 4.860 2.785 0.473 0.826 M-7 — 1.0 — — 1=2 ¼ðHmax à HminÞ ÃValue in parenthesis are obtained from 1H NMR data.
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