Regularities of the radical copolymerization of dodecyl (meth) acrylate and a new cationic monomer N-(dibutylaminomethyl) methacrylamide
https://doi.org/10.35164/0554-2901-2021-9-10-18-21
Abstract
The regularities of radical copolymerization of dodecyl methacrylate (DMA) or dodecyl acrylate (DA) with a new cationic monomer - N-(dibutylaminomethyl) methacrylamide (DBAMMA) in toluene solutions were determined. The copolymers formed at low conversions in the DMA-DBAMMA system are enriched in ether units, and in the DA-DBAMMA system - in aminoamide units. The relative activities of comonomers determined by the Feineman-Ross and Kehlen-Tudosh methods in the first case were 1.56-1.60 (DMA) and 0.87-0.89 (DBAMMA), in the second case - 0.53-0.64 (DA) and 0.80-0.90 (DBAMMA).
About the Authors
I. R. ArifullinRussian Federation
Nizhny Novgorod
K. V. Shirshin
Russian Federation
Nizhny Novgorod
Dzerzhinsk, Nizhny Novgorod region
O. A. Kazantsev
Russian Federation
Nizhny Novgorod
M. V. Savinova
Russian Federation
Nizhny Novgorod
T. A. Ryabova
Russian Federation
Nizhny Novgorod
References
1. Пат. 6323164 США. Dispersant (meth) acrylate copolymers having excellent low temperature properties / G.P. Liesen, S. Srinivasan; Ethyl Corporation (Richmond, VA); заявл. 01.01.2000; опубл. 27.11.2001.
2. Пат. 20020086965 США. Dispersant-viscosity improvers for lubricating oil compositions / M.R. Sivik, C.P. Bryant; заявл. 23.01.2000; опубл. 04.07.2002.
3. Forster, R.E. Hydrophobically modified polyacrylamide block copolymers for fast, high-resolution DNA sequencing in microfluidic chips / R.E. Forster, T.N. Chiesl, C. P. Fredlake // Electrophoresis. – 2008. – Vol. 29, N 23. – P. 4669-4676.
4. Yahaya, G.O. Solution behavior of hydrophobically associating watersoluble block copolymers of acrylamide and N-benzylacrylamide / G.O. Yahaya, A.A. Ahdab, S.A. Ali et al. // Polym. – 2001. – Vol. 42, N 8. – P. 3363-3372.
5. Zou, W. Adsorption of hydrophobically modified polyacrylamide P(AMNaAA-C16DMAAC) on model coal and clay surfaces and the effect on selective flocculation of fine coal / W. Zou, L. Gong, J. Huang // Miner. Eng. – 2019. – Vol. 142. – P. 105887.
6. Пат. 9777098 США. Polyalkyl (meth) acrylate for improving lubricating oil properties / Eisenberg B., Janssen D., Suchert E., Stihulka M.K., Voigt L.; Evonik Oil Additives GmbH; заявл. 27.06.2011; опубл. 03.10.2017.
7. Пат. 6323164 США. Dispersant (meth) acrylate copolymers having excellent low temperature properties / Liesen G., Srinivasan S.; Ethyl Corporation; заявл. 01.11.2000; опубл. 27.11.2011.
8. Si, K. Radical Copolymerization of N-[(3-Dimethylamino) propyl] Acrylamide (or Methacyrlamide) with Methyl Acrylate (or Methacrylate) / K. Si, K.Y. Qiu // J. Macromol. Sci. Pure Appl. – 1995. – Vol. 32, N 8. – P. 1139-1148.
9. Kazantsev, O.A. Copolymerization of amine-containing monomers and dodecyl (meth)acrylate in toluene: controlling compositional heterogeneity / O.A. Kazantsev, D.M. Kamorin, A.P. Sivokhin, et al. // J Polym. Res. – 2014. – Vol. 21. – P. 353-358.
10. Kazantsev, O.A. Two-stage one-pot synthesis of N-(dibutylaminomethyl)methacrylamide by Mannich reaction under mild conditions with high yield / O.A. Kazantsev, I.R. Arifullin, M.V. Savinova, et al. // React. Chem. Eng. – 2020. – N5. – P. 1791-1797.
11. Lopez, D. Effect of thermal treatment and radiation on (N,Ndimethylaminopropyl)acrylamide copolymers in the solid state / D. Lopez, P. Plata, G. Burillo // Radiat. Phys. Chem. – 1996. – Vol. 47, N 2. – P. 251-256.
12. Каморин, Д.М. Особенности мономерной ассоциации высших N-алкилакриламидов и алкилакрилатов в толуоле / Д.М. Каморин, К.В. Ширшин, М.С. Румянцев и др.// Пластические массы. – 2017. – №11-12. – С. 22-26.
13. Sivokhin, A.P. Radical copolymerization of higher alkyl methacrylates with acrylic esters and amides in toluene: influence of monomer association on copolymer composition /A.P. Sivokhin, S.I. Kamorina, M. Rumyantsev, et. al. // J. Polym. Res. – 2016. – Vol. 23, N5. – P. 1-8.
14. Fineman, M. Linear method for determining monomer reactivity ratios in copolymerization / M. Fineman, S.D. Ross // Journal of Polymer Science. ‒ 1950. ‒ Vol. 5, N2. ‒ P. 259-262.
15. Kelen, T Analysis of the linear methods for determining copolymerization reactivity ratios. I. A new improved linear graphic method / T. Kelen, F. Tudos // J. Macromol. Sci. Chem. – 1975. – Vol. 9, N1. – P. 1-27.
Review
For citations:
Arifullin I.R., Shirshin K.V., Kazantsev O.A., Savinova M.V., Ryabova T.A. Regularities of the radical copolymerization of dodecyl (meth) acrylate and a new cationic monomer N-(dibutylaminomethyl) methacrylamide. Plasticheskie massy. 2021;(9-10):18-21. (In Russ.) https://doi.org/10.35164/0554-2901-2021-9-10-18-21