This article presents the results of the quaternary ammonium salt synthesis containing nitrogen heterocyclic fragments, including N, N-diallylbenzoimidazolyl bromide and N, N-diallylbenzotriazolyl bromide and their copolymerization with acrylic acid. The synthesis of allyl monomers - N, N-diallylbenzotriazolium bromide (DABTB) and N, N-diallylbenzoimidazolium bromide (DABIB) was carried out by reacting allyl bromide with benzotriazole and benzoimidazole at a temperature of 50-60 °C in an allylation reaction in an organic solvent. The obtained salts were recrystallized from ethyl alcohol. The substance is obtained in the form of colorless crystal, its yield is 80-85%. The purity of the obtained salt was checked by TLC. The radical polymerization of N, N-diallylbenzotriazolium bromide in aqueous solution in the presence of a radical initiator potassium persulfate at a temperature of 60-70 °C is in an inert nitrogen gas. The polymer yield is up to 40%. Binary copolymerization of the synthesized salt of N, N–diallybenzotriazolium bromide with acrylic acid was carried out. It was found that copolymerization does not occur in the absence of an initiator. Copolymerization was carried out in organic solvents in the presence of the radical initiator azobisisobutyronitrile. After the end of the copolymerization reaction, the reaction mixture was precipitated with benzene and dried to constant weight. Dried copolymers to constant weight were analyzed for the content of carboxyl groups by titration of the samples with 0.1 N KOH solution. The synthesized copolymers dissolve well in water, ethanol, acetone, but do not dissolve in toluene and benzene. The results obtained show that the composition of the copolymers depends on the initial ratio of the monomer mixture and the content of each monomer in the copolymer changes symbatically with its initial content. The structure of the synthesized monomers and (co) polymers has been proved by IR spectral studies. According to the IR spectral results, the spectrum of the synthesized copolymer is radically different from the spectra of the starting comonomers.
№ | Author name | position | Name of organisation |
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1 | Maksumova O.S. | Professor | Tashkent Institute of Chemical Technology |
2 | Kedelbaev B.S. | Professor | M.Auezov South Kazakhstan State University |
3 | Tadjieva S.A. | Doktarant | Tashkent Institute of Chemical Technology |
№ | Name of reference |
---|---|
1 | 1. Esmurziev A.M., Hashirov S.J., Martynenko A.I., Kabanov E.Y., Popova N.I., Siobov N.A., Malkanduev YU. Radical homo (co) polymerization of acrylate and methacrylate guanidins in water media. /News. Sowing. - Kavk. the region, is gray. Natures. sciences. 2003, № 6, p. 56-59. |
2 | 2. Solovieva O.M, Kalyazina O.V, Murzabekova G. G., Topchiev D. A., Radical block-polymerization involving quaternary diallyl ammonium salts. Theses of the reports of the 2nd All-Russian Kargin Symposium "Chemistry and Physics of Polymers at the Beginning of the XXI Century," 2000, Vol. 2, С.24, Montenegro |
3 | 3. Kukharev B F, Lelyukh T.F, Kalyazina O.V, Murzabekova T.G, Doslov O.I. Cationic polyelectrolytes with tertiary nitrogen atom in the main chain Journal of Irkutsk State University of Technical University, 2004, № 4, with 133 136 |
4 | 4. Kenawi E.R., Abdel-Hey F.I., El-Shanshuri A.E.-R.R., El-Newhi M.H. Biologically active polymers. V. Synthesis and antimicrobial activity of modified poly (glycidyl methacrylate-co-2-hydroxyethyl methacrylate) derivatives with quaternary ammonium and phosphonium salts. J. PolymSci A1. 2002; 40 (14): 2384-93. |
5 | 5. Evdokimov M. V., Horsovyrina T. A. Synthesis of polyelectrolytes based on mixed acrylic anhydride and chloroacetic acids//Topical problems of ecology, biology and chemistry: materials of the Republican Scientific and Practical Conference/MarSU. Yoshkar-Ola, 2013. Issue. 4. Page 130-133. |
6 | 6. Kurbatova M. V., Podkovyrina T. A. Polymerization of quaternary ammonium salts based on allyl bromide//Topical problems of ecology, biology and chemistry: conference materials on the results of NIR for 2010/MarSU. Yoshkar-Ola, 2011. Page 90-92. |
7 | 7. Topchiev D. A., Malkanduev Yu. A. Cationic polyelectrolytes of poly-N, N-dialkyl-N, N-diallylammonium halides: peculiarities of formation processes, properties and applications. Nalchik, 1997. – Page. 240. |
8 | 8. Jalilov A.T., Malkanduev Yu.A., Mikitayev A.K. Synthesis and properties of reactive polymers. Moscow: "D.I.Mendeleeva RSTU," 2011. -282 p. |
9 | 9. Maksumova A.S. Water-soluble polymers and copolymers based on dimethylaminoethyl methacrylate with galloid allyls//Journal of GulGU, 2004. - No. 1.-С.14-17. |
10 | 10. L.M. Potiha, A. R. Turelik, V. A. Kovtunenko, A. V. Turov, HGS, 95 (2010). [Chem. Heterocycl. Compd., 46, 82 (2010).] |
11 | 11. L. M. Potiha, A. R. Turelik, V. A. Kovtunenko, A. V. Turov, HGS, 275 (2010). [Chem. Heterocycl. Compd., 46, 223 (2010).] |
12 | 12. Soloviev O.M., Klazina O.B., Murzabekova T.G., Topchiev D.A. Radical block-polymerization involving quaternary diallyl ammonium salts. Theses of reports of the 2nd All-Russian Kargin Symposium "Chemistry and Physics of Polymers at the Beginning of the XXI Century." Montenegolovka, 2000. -H. 2. – Page. 24. |
13 | 13. N.A. Siobov, A.I. Martynenko, E.Y. Kabanov, N.I. Popov, S.J. Hashirov, Y.A. Malkanduyev. Copolymers erization of dimethyl ammonium chloride and methacrylate guanidine dialyl at deep conversion degrees//Izvia of higher education institutions. North Caucasian region. Natural Sciences, 2006. - № 3. -С.33-36. |
14 | 14. Muhammad Jawwad Saif, Jamil Anwar, Nazeran Idrees, Naveed Athir, Tanvir Hussain Bokhariand Waheed uz-Zaman. Acrylate copolymers containing benzimidazolium moieties: synthesis and antimicrobial applications. Polymers 2014; 14(6): 391–396 |
15 | 15. G.B. Vladina, I.V. Yakunina. Laboratory workshop on organic chemistry. Tambov: Tamb publishing house. State. Tekhn. Un-ta, 2004. 80 pages. |