Preview

Plasticheskie massy

Advanced search

Copolymerization of N-[3-dialkylaminopropyl]methacrylamides with acrylic amides and esters in organic solvents

https://doi.org/10.35164/0554-2901-2023-1-2-21-26

Abstract

The radical copolymerization of N-[3-(dialkylamino)-propyl]methacrylamides with a number of (meth)acrylic amides and esters in organic solvents over a wide range of molar ratios has been studied. Co-polymerisation constants for five polymerisation systems in 1,4-dioxane and toluene have been determined by the Feinman and Ross method. The influence of the solvent on the kinetics of the copolymerization of the studied monomers was found, which manifests itself in a change of the reactivity ratios of the monomers upon varying the polarity of the medium. For the obtained polymers, the presence of thermosensitive properties in aqueous solutions and the effect of the concentration and composition of copolymers on their solubility in water were shown.

About the Authors

A. Yu. Sadikov
Nizhny Novgorod State Technical University n.a. R.E. Alekseev
Russian Federation

Nizhny Novgorod



O. A. Kazantsev
Nizhny Novgorod State Technical University n.a. R.E. Alekseev
Russian Federation

Nizhny Novgorod



D. M. Kamorin
Nizhny Novgorod State Technical University n.a. R.E. Alekseev
Russian Federation

Nizhny Novgorod



A. S. Simagin
Nizhny Novgorod State Technical University n.a. R.E. Alekseev
Russian Federation

Nizhny Novgorod



I. R. Arifullin
Nizhny Novgorod State Technical University n.a. R.E. Alekseev
Russian Federation

Nizhny Novgorod



D. V. Orekhov
Nizhny Novgorod State Technical University n.a. R.E. Alekseev
Russian Federation

Nizhny Novgorod



References

1. Heitner H.I., Flocculating agents. In: Kroschwitz J.I., HoweGrant M., editors. Kirk-Othmer encyclopedia of chemical technology. Vol. 11. New York (NY): Wiley; 2004. p. 623–647.

2. Hagiopol C., Johnston J.W. (2012) Chemistry of modern paperma king. CRC Press. doi.org/10.1201/b11011.

3. Wever D.A.Z., Picchioni F., Broekhuis A.A. Polymers for enhanced oil recovery: A paradigm for structure–property relationship in aqueous solution // Progress in Polymer Science, 2011. – V. 36. – I. 11. – P. 1558–1628.

4. Herrero M., Bernal J., Velasco D., Elvira C., Cifuentes A. Connections between structure and performance of four cationic copolymers used as physically adsorbed coatings in capillary electrophoresis // J Chromatogr A, 2010. – V. 1217. – I. 48. – P. 7586–7592. doi: 10.1016/j.chroma.2010.09.063.

5. Liu M., Chen Z., Yu S., Wu D., Gao C. Thin-film composite polyamide reverse osmosis membranes with improved acid stability and chlorine resistance by coating N-isopropylacrylamide-co-acrylamide copolymers // Desalination, 2011. – V. 270. – I. 1–3. – P. 248–257. DOI: 10.1016/j.desal.2010.11.052.

6. Aseyev V. Non-ionic Thermoresponsive Polymers in Water / V. Aseyev. – Berlin.: Heidelberg, 2010. – P. 89.

7. Döring A., Birnbaum W., Kuckling D. Responsive hydrogels – structurally and dimensionally optimized smart frameworks for applications in catalysis, micro-system technology and material science // Chem. Soc. Rev., 2013. – 42. – P. 7391–7420. DOI: 10.1039/C3CS60031A.

8. Gil E.S., Hudson S.M. Stimuli-reponsive polymers and their bioconjugates // Prog. Polym. Sci., 2004. – 29. – P. 1173–1222. DOI: 10.1016/j.progpolymsci.2004.08.003.

9. Kuckling D. Stimuli-Responsive Polymer Systems // In: Polymer Science: A Comprehensive Reference, 2012. – P. 377–413. DOI: 10.1016/B978-0-444-53349-4.00214-4.

10. Schmitz S., Ritter H. Access to Poly{N-[3-(dimethylamino)propyl] (meth)acrylamide} via Microwave-Assisted Synthesis and Control of LCST-Behavior in Water // Macromol. Rapid Commun., 2007. – 28. – P. 2080–2083.

11. Song Z., Wang K., Gao C., Wang S., Zhang W. A New Thermo-, pH-, and CO2-Responsive Homopolymer of Poly[N-[2-(diethylamino)ethyl]acrylamide]: Is the Diethylamino Group Underestimated? // Macromolecules, 2016. – V. 49. – P. 162–171.

12. Caykara T., Birlik G. Synthesis and Network Parameters of Hydrophobic Poly(N-[3-(dimethylaminopropyl)]methacrylamide-co-lauryl acrylate) Hydrogels // Journal of Applied Polymer Science, 2006. – V. 101. – P. 4159–4166

13. Das A., Mehndiratta M., Chattopadhyay P., Ray A.R. Prolonged Zero-Order BSA Release from pH-Sensitive Hydrogels of Poly(AAcco-DMAPMA) Having Rich Nano Through Micro Scale Morphology // Journal of Applied Polymer Science, 2010. – V. 115. – P. 393–403.

14. Eke I., Elmas B., Tuncel M., Tuncel A. A new, highly stable cationic-thermosensitive microgel: Uniform isopropylacrylamide-dimethylaminopropylmethacrylamide copolymer particles // Colloids and Surfaces A: Physicochem. Eng. Aspects, 2006. – 279. – P. 247–253.

15. Jean B., Bokias G., Lee L.-T., Iliopoulos I., Cabane B. Microphase separation of cationic poly(N-isopropylacrylamide) copolymers in water: Effect of the migration of charges // Colloid Polym Sci, 2002. – 280. – P. 908–914.

16. Mishra R.K., Ramasamy K., Majeed A.B.A. pH-Responsive Poly(DMAPMA-co-HEMA)-Based Hydrogels for Prolonged Release of 5-Fluorouracil // Journal of Applied Polymer Science, 2012. – V. 126. - P. E98–E107.

17. Demirel G.B., Caykara T. Reentrant Phase Transition and Fast Responsive Behaviors of Poly{N-[3-(dimethylaminopropyl)] Methacrylamide} Hydrogels Prepared in Poly(ethylene glycol) Solutions // Journal of Applied Polymer Science, 2009. – V. 113. P. 547–552.

18. Beatriz A. Pineda-Contreras, Fangyao Liu, Seema Agarwal. Importance of compositional homogeneity of macromolecular chains for UCST-type transitions in water: Controlled versus conventional radical polymerization // Journal Of Polymer Science, Part A: Polymer Chemistry, 2014. – 52. – P. 1878–1884.

19. Kamorin D.M., Rumyantsev M., Kazantsev O.A., Sivokhin A.P., Kamorina S.I. Influences of monomer self-association on the radical solution homopolymerization of N-[3-(dimethylamino)propyl] (meth)acrylamide // J. Appl. Polym. Sci., 2016. – 134. – 44412. DOI: 10.1002/APP.44412.

20. Kazantsev O.A., Samodurova S.I., Sivokhin A.P., Goncharova O.S., Kamorin D.M., Shirshin K.V., Orekhov D.V. Homopolymerization of higher alkyl (meth)acrylates and N-alkyl acrylamides in toluene: an effect of monomer self-organization // J Polym Res, 2013. – 20. – 52. DOI: 10.1007/s10965-012-0052-x.

21. Kazantsev O.A., Samodurova S.I., Kamorin D.M., Rumyantsev M., Sivokhin A.P., Radical copolymerization of higher alkyl methacrylates with acrylic esters and amides in toluene: influence of monomer association on copolymer composition // J. Polym Res, 2016. – 23. – 89. DOI 10.1007/s10965-016-0991-8.

22. Kazantsev O., Sivokhin A., Samodurova S., Orekhov D., Korotkova T. Copolymerization of amine-containing monomers and dodecyl (meth)acrylate in toluene: controlling compositional heterogeneity // Journal of Polymer Research, 2014. – V.21 – №2. DOI:10.1007/s10965-013-0353-8.

23. Казанцев О.А., Сивохин А.П., Орехов Д.В., Каморин Д.М. Влияние условий синтеза на композиционную неоднородность сополимеров высших N-алкилакриламидов и бутил(мет)акрилата // Журнал прикладной химии, 2012. – Т. 85. – №5. – С. 805–812.

24. Казанцев О.А., Самодурова С.И., Ширшин К.В., Сивохин А.П., Орехов Д.В., Каморин Д.М. Влияние условий синтеза на композиционную неоднородность сополимеров высших N-алкилакриламидов и додецил(мет)акрилата // Пластические массы, 2012. – №11. – С. 21–27.

25. Bezzaoucha F. New amphiphilic polyacrylamides: Synthesis and characterisation of pseudo-micellar organisation in aqueous media // Eur Polym J., 2007. – V. 43. – P. 4440–4452.

26. Orekhov D.V., Kamorin D.M., Simagin A.S. et al. Molecular brushes based on copolymers of alkoxy oligo(ethylene glycol) methacrylatesand dodecyl(meth)acrylate: features of synthesis by conventional free radical polymerization // Polymer Bulletin, 2021. – 78. – 5833–5850. DOI: 10.1007/s00289-020-03390-2.

27. Fineman M., Ross S. D. Linear method for determining monomer reactivity ratios in copolymerization // J. Polym. Sci, 1950. – V. 5. – №2. P. 259–265.

28. Мягченков В.А., Френкель С.Я. Композиционная неоднородность сополимеров. Ленинград: Химия, 1988.

29. Семчиков Ю.Д. Высокомолекулярные соединения. М.: Академия. 2010. 368 с.

30. Каморин Д.М., Ширшин К.В., Симагин А.С., Кавтрова В.Д., Сак Ю.В., Тимченко Е.А. Растворные свойства амфифильных амино- и олигоэтиленгликольсодержащих метакриловых сополимеров // Пластические массы, 2021. – №11–12. – C. 40–42. DOI: 10.35164/0554-2901-2021-11-12-40-42.


Review

For citations:


Sadikov A.Yu., Kazantsev O.A., Kamorin D.M., Simagin A.S., Arifullin I.R., Orekhov D.V. Copolymerization of N-[3-dialkylaminopropyl]methacrylamides with acrylic amides and esters in organic solvents. Plasticheskie massy. 2023;1(1-2):21-26. (In Russ.) https://doi.org/10.35164/0554-2901-2023-1-2-21-26

Views: 213


Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 License.


ISSN 0554-2901 (Print)