Abstract
Three cationic copolymers methacryloxyethyl trimethyl ammonium chloride-butyl acrylate-acrylamide (MTAC-BA-AM terpolymer) were designed and synthesized by emulsion polymerization. Their structures were confirmed by FT-IR and 1H NMR. The effect of content of hydrophobic monomer butyl acrylate (BA) in MTAC-BA-AM terpolymer on surface activities, flocculation and antibacterial properties were investigated. The study of surface tension shows that MTAC-BA-AM terpolymer has good surface activity due to the introduction of hydrophobic monomer BA. The flocculation experiment showed that the light transmittance of the kaolin suspension supernatant was 98.13% when the dose of MTAC-BA-AM terpolymer in the kaolin suspension was 0.03 mg/L, which was obviously better than the P(MTAC-AM) (91.02%) without hydrophobic modification of BA. The bacteriostatic experiment of MTAC-BA-AM terpolymer showed that as the content of hydrophobic monomer BA in MTAC-BA-AM terpolymer increased the inhibitory rate of MTAC-BA-AM terpolymer aginst Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus)
Abstract
Drei kationische Copolymere Methacryloxyethyltri-methylammoniumchlorid-Butylacrylat-Acrylamid (MTAC-BA-AM-Terpolymer) wurden entwickelt und durch Emulsionspolymerisation synthetisiert. Ihre Strukturen wurden durch FT-IR und 1H NMR bestätigt. Der Einfluss des Gehalts des hydrophoben Monomers Butylacrylat (BA) im MTAC-BA-AM-Terpolymer auf die Oberflächenaktivitäten, die Flockung und die antibakteriellen Eigenschaften wurden untersucht. Die Untersuchung der Oberflächenspannung zeigt, dass MTAC-BA-AM-Terpolymer aufgrund der Einführung des hydrophoben Monomers BA eine gute Oberflächenaktivität aufweist. Das Flockungsexperiment zeigte, dass die Lichtdurchlässigkeit des Überstandes der Kaolinsuspension 98,13% betrug, wenn die Dosis des MTAC-BA-AM-Terpolymers in der Kaolinsuspension 0,03 mg/L betrug, was offensichtlich besser war als das P(MTAC-AM) (91,02%) ohne hydrophobe Modifikation durch BA. Das bakteriostatische Experiment von MTAC-BA-AM Terpolymer zeigte, dass mit der Erhöhung des Gehalts des hydrophoben Monomers BA im MTAC-BA-AM Terpolymer die Inhibierungsgeschwindigkeit von MTAC-BA-AM Terpolymer gegen Escherichia coli (E. coli) und Staphylococcus aureus (S. aureus) zunahm.
About the authors
Geng Su is working for a master’s degree at the China Research Institute of Daily Chemical Industry. His research field centers on the synthesis and application of poly quaternary ammonium salts.
Ya-jie Jiang is an engineer at the China Research Institute of Daily Chemical Industry. Her research interest is in the synthesis and investigation of novel quaternary ammonium salts.
Hong-bin Ju is an engineer at the China Research Institute of Daily Chemical Industry. His research interest is in the synthesis of quaternary ammonium hydroxide.
Ya-kui Wang is an engineer at the China Research Institute of Daily Chemical Industry. His research interest is in the synthesis and investigation of quaternary ammonium salts with new counterions.
Shui-Xin Yu is an engineer at Shanghai ICAN Chemical S&T Co., Ltd. His research interest is in the synthesis and investigation of quaternary ammonium salts.
Ye-Yuan Luo is an engineer at Shanghai ICAN Chemical S&T Co., Ltd. Her research interest is in the application of cationic surfactants.
Tao Geng is a professor at the China Research Institute of Daily Chemical Industry. His research interests are in the synthesis and investigation of cationic surfactants.
Acknowledgements
The authors gratefully appreciate the financial support from the Nation Key R&D Program (2017YFB0308900) and Project of JALA Research Funds (JALA 2017).
References
1 El-Shafei, A., El Shemy, M. and Abou-Okeil, A.: Eco-friendly finishing agent for cotton fabrics to improve flame retardant and antibacterial properties. Carbohyd. Polym. 118 (2015) 83–90. DOI:10.1016/j.carbpol.2014.11.00710.1016/j.carbpol.2014.11.007Search in Google Scholar PubMed
2 El-Rafie, M., Ahmed, H. B. and Zahran, M. K.: Characterization of nanosilver coated cotton fabrics and evaluation of its antibacterial efficacy. Carbohyd. Polym. 107 (2014) 174–181. DOI:10.1016/j.carbpol.2014.02.02410.1016/j.carbpol.2014.02.024Search in Google Scholar PubMed
3 Tashiro, T.: Antibacterial and bacterium adsorbing macromolecules. Macromol. Mater. Eng. 286 (2001) 63–87. DOI:10.1002/1439-2054(20010201)286:210.1002/1439-2054(20010201)286:2Search in Google Scholar
4 Ilker, M. F., Nüsslein, K., Tew, G. N. and Coughlin, E. B.: Tuning the hemolytic and antibacterial activities of amphiphilic polynorbornene derivatives. J. Am. Chem. Soc. 126 (2004) 15870–15875. DOI:10.1021/ja045664d10.1021/ja045664dSearch in Google Scholar PubMed
5 Dragan, S. and Ghimici, L.: Viscometric behaviour of some hydrophobically modified cationic polyelectrolytes. Polymer, 42 (2001) 2887–2891. DOI:10.1016/S0032-3861(00)00690-X10.1016/S0032-3861(00)00690-XSearch in Google Scholar
6 Berlinova, I. V., Dimitrov, I. V. and Vladimirov, N. G.: Preparation and solution behaviour of graft copolymers with cationic groups in polyoxyethylene side chains. Polymer. 41 (2000) 6431–6438. DOI:10.1016/S0032-3861(99)00883-610.1016/S0032-3861(99)00883-6Search in Google Scholar
7 Zhang, X., Jiang, G., Xuan, Y., Wang, L. and Huang, X.: Associating copolymer acrylamide/diallyldimethylammonium chloride/butyl acrylate/2-acrylamido-2-methylpropanesulfonic acid as a tackifier in clay-free and water-based drilling fluids. Energy. Fuel. 31 (2017) 4655–4662. 6b02599. DOI:10.1021/acs.energyfuels10.1021/acs.energyfuelsSearch in Google Scholar
8 Lü, T., Qi, D., Zhao, H. and Cheng, Y.: Synthesis of hydrophobically modified flocculant by aqueous dispersion polymerization and its application in oily wastewater treatment. Polym. Eng. Sci. 55 (2015) 1–7. DOI:10.1002/pen.2385610.1002/pen.23856Search in Google Scholar
9 Li, X., Zheng, H., Gao, B., Zhao, C. and Sun, Y.: UV-initiated polymerization of acid-and alkali-resistant cationic flocculant P (AM-MAPTAC): Synthesis, characterization, and application in sludge dewatering. Sep. Purif. Technol. 187 (2017) 244–254. DOI:10.1016/j.seppur.2017.06.03510.1016/j.seppur.2017.06.035Search in Google Scholar
10 Yang, Z. L., Gao, B. Y., Li, C. X., Yue, Q. Y. and Liu, B.: Synthesis and characterization of hydrophobically associating cationic polyacrylamide. Chem. Eng. J. 161 (2010) 27–33. DOI:10.1016/j.cej.2010.04.01510.1016/j.cej.2010.04.015Search in Google Scholar
11 Cao, X., Tan, Y., Xu, G. and Wu, D.: Aggregation Behavior of Cationic Copolymer Methacryloxyethyl Trimethyl Ammonium Chloride-Butyl Acrylate-Acrylamide in Aqueous Solution. J. Disper. Sci. Technol. 29 (2008) 70–76. DOI:10.1080/0193269070168841710.1080/01932690701688417Search in Google Scholar
12 Li, J. J., Jiang, H. Q., Hou, J. R. and Wang, S. L.: The effects of oil displacement efficiency and conformance efficiency on viscosity of asp flooding in a heterogeneous reservoir. Petrol. Sci. Technol. 32 (2014) 830–839. DOI:10.1080/10916466.2010.52954810.1080/10916466.2010.529548Search in Google Scholar
13 Chen, W., Zheng, H., Guan, Q., Teng, H., Zhao, C. and Zhao, C.: Fabricating a flocculant with controllable cationic microblock structure: characterization and sludge conditioning behavior evaluation. Ind. Eng. Chem. Res. 55 (2016) 2892–2902. DOI:10.1021/acs.iecr.5b0420710.1021/acs.iecr.5b04207Search in Google Scholar
14 Guan, Q., Zheng, H., Zhai, J., Liu, B., Sun, Y., Wang, Y. and Zhao, C.: Preparation, characterization, and flocculation performance of P (acrylamide-co-diallyldimethylammonium chloride) by UV-initiated template polymerization. J. Appl. Polym. Sci. 132 (2015) 13. DOI:10.1002/app.4174710.1002/app.41747Search in Google Scholar
15 Kumar, K., Adhikary, P., Karmakar, N. C., Gupta, S., Singh, R. P. and Krishna-moorthi, S.: Synthesis, characterization and application of novel cationic and amphoteric flocculants based on amylopectin. Carbohyd. Polym. 127 (2015) 275–281. DOI:10.1016/j.carbpol.2015.03.04410.1016/j.carbpol.2015.03.044Search in Google Scholar PubMed
16 Gumfekar, S. P., Rooney, T. R., Hutchinson, R. A. and Soares, J. B.: Dewatering Oil Sands Tailings with Degradable Polymer Flocculants. ACS. Appl. Mater. Inter. 9 (2017) 36290–36300. DOI:10.1021/acsami.7b1030210.1021/acsami.7b10302Search in Google Scholar PubMed
17 Dowling, K. C. and Thomas, J. K.: A novel micellar synthesis and photophysical characterization of water-soluble acrylamide-styrene block copolymers. Macromolecules. 23 (1990) 1059–1064. DOI:10.1021/ma00206a02510.1021/ma00206a025Search in Google Scholar
18 Wu, Y. M., Wang, Y. P., Yu, Y. Q., Xu, J. and Chen, Q. F.: Dispersion polymerization of acrylamide with 2-acrylamido-2-methyl-1-propane sulfonate in aqueous solution. J. Appl. Polym. Sci. 102 (2006) 2379–2385. DOI:10.1002/app.2449410.1002/app.24494Search in Google Scholar
19 Jia, X. and Zhang, Y.: Effects of maintaining temperature and time on properties and structures of poly (dimethyldiallylammonium chloride). J. Appl. Polym. Sci. 125 (2012) 1–9. DOI:10.1002/app.3435410.1002/app.34354Search in Google Scholar
20 Feng, L., Zheng, H., Tang, X., Zheng, X., Liu, S., Sun, Q. and Wang, M.: The investigation of the specific behavior of a cationic block structure and its excellent flocculation performance in high-turbidity water treatment. RSC. Adv. 8 (2018) 15119–15133. DOI:10.1039/C8RA02006J10.1039/C8RA02006JSearch in Google Scholar
21 Zhang, C., Jiang, Y., Ju, H., Wang, Y. and Geng, T.: “Organic counterion" modified quaternary ammonium salt: Impact on antibacterial activity & application properties. J. Mol. Liq. 241 (2017) 638–645. DOI:10.1016/j.molliq.2017.06.06210.1016/j.molliq.2017.06.062Search in Google Scholar
22 Raduan, N. H., Horozov, T. S. and Georgiou, T. K.: “Comb-like" non-ionic polymeric macrosurfactants. Soft. Matter. 6 (2010) 2321–2329. DOI:10.1039/b926822 g10.1039/b926822gSearch in Google Scholar
23 Bai, Y., Ma, X., Wang, W., Yin, Q., Du, Z. and Wang, G.: Synthesis, aggregation and dispersity properties of novels amphiphilic comb-like terpolymers. Colloid. Surface. A. 526 (2017) 40–47. DOI:10.1016/j.colsurfa.2016.11.01110.1016/j.colsurfa.2016.11.011Search in Google Scholar
24 Wu, X., Qiao, Y., Yang, H. and Wang, J.: Self-assembly of a series of random copolymers bearing amphiphilic side chains. J. Colloid. Interf. Sci. 349 (2010) 560–564. DOI:10.1016/j.jcis.2010.05.09310.1016/j.jcis.2010.05.093Search in Google Scholar PubMed
25 Zhu, J., Zheng, H., Jiang, Z., Zhang, Z., Liu, L., Sun, Y. and Tshukudu, T.: Synthesis and characterization of a dewatering reagent: cationic polyacrylamide (P (AM–DMC–DAC)) for activated sludge dewatering treatment. Desalin. Water. Treat. 51 (2013) 2791–2801. DOI:10.1080/19443994.2012.74957910.1080/19443994.2012.749579Search in Google Scholar
26 Ma, J., Fu, K., Fu, X., Guan, Q., Ding, L., Shi, J. and Jiang, L.: Flocculation properties and kinetic investigation of polyacrylamide with different cationic monomer content for high turbid water purification. Sep. Purif. Technol. 182 (2017) 134–143. DOI:10.1016/j.seppur.2017.03.04810.1016/j.seppur.2017.03.048Search in Google Scholar
27 Zhang, W., Du, Z., Chang, C. H. and Wang, G.: Preparation and properties of comb-like surfactants containing poly (ethylene oxide) methyl ether grafts. J. Colloid. Interf. Sci. 33 (2009) 563–568. DOI:10.1016/j.jcis.2009.05.04310.1016/j.jcis.2009.05.043Search in Google Scholar PubMed
28 Zhao, C., Zheng, H., Sun, Y., Zhang, S., Liang, J., Liu, Y. and An, Y.: Evaluation of a novel dextran-based flocculant on treatment of dye wastewater: Effect of kaolin particles. Sci. Total. Environ. 640 (2018) 243–254. DOI:10.1016/j.scitotenv.2018.05.28610.1016/j.scitotenv.2018.05.286Search in Google Scholar PubMed
29 Theodoly, O., Ober, R. and Williams, C. E.: Adsorption of hydrophobic polyelectrolytes at the air/water interface: Conformational effect and history dependence. Eur. Phys. J. E. 5 (2001) 51–58. DOI:10.1007/s10189017008610.1007/s101890170086Search in Google Scholar
30 Yang, Z., Shang, Y., Lu, Y., Chen, Y., Huang, X., Chen, A. and Cheng, R.: Flocculation properties of biodegradable amphoteric chitosan-based flocculants. Chem. Eng. J. 172 (2011) 287–295. DOI:10.1016/j.cej.2011.05.10610.1016/j.cej.2011.05.106Search in Google Scholar
31 Abid, C. Z., Chattopadhyay, S., Mazumdar, N. and Singh, H.: Synthesis and characterization of quaternary ammonium PEGDA dendritic copolymer networks for water disinfection. J. Appl. Polym. Sci. 116 (2010) 1640–1649. DOI:10.1002/app.3151010.1002/app.31510Search in Google Scholar
32 Ikeda, T., Tazuke, S. and Suzuki, Y.: Biologically active polycations, 4. Synthesis and antimicrobial activity of poly (trialkylvinylbenzylammonium chloride) s. Die. Makromolekulare. Chemie. 185 (1984) 869–876. DOI:10.1002/macp.1984.02185050310.1002/macp.1984.021850503Search in Google Scholar
33 Zhang, A., Liu, Q., Lei, Y., Hong, S. and Lin, Y.: Synthesis and antimicrobial activities of acrylamide polymers containing quaternary ammonium salts on bacteria and phytopathogenic fungi. React. Funct. Polym. 88 (2015) 39–46. DOI:10.1016/j.reactfunctpolym.2015.02.00510.1016/j.reactfunctpolym.2015.02.005Search in Google Scholar
34 Meng, X., Liang, L., Liu, B., Peng, G., Wang, B., Chen, H. and Luo, R.: Influence of 2-methylacryloyLxyethyl trimethyl ammonium chloride on the properties of cationic poly (vinyl acetate-butyl acrylate-DMC) copolymer emulsions. J. Macromol. Sci. A. 50 (2013) 185–192. DOI:10.1080/10601325.2013.74238110.1080/10601325.2013.742381Search in Google Scholar
35 Gilbert, P. and Moore, L. E.: Cationic antiseptics: diversity of action under a common epithet. J. Appl. Microbiol. 99 (2005) 703–715. PMid:16162221; DOI:10.1111/j.1365-2672.2005.02664.x10.1111/j.1365-2672.2005.02664.xSearch in Google Scholar PubMed
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