plasticnewsПластические массыPlasticheskie massy0554-2901PLASTMASSY Publishing House (Moscow)10.35164/0554-2901-2023-5-6-48-52plasticnews-888Research ArticleСИНТЕЗ И ТЕХНОЛОГИЯSYNTHESIS AND TECHNOLOGYВлияние амфифильных сополимеров олиго(этиленгликоль)метакрилатов на синтез N-(дибутиламинометил)метакриламида в водно-органической эмульсииEffect of amphiphilic copolymers of oligo(ethylene glycol)methacrylates on the synthesis of N-(dibutylaminomethyl)methacrylamide in an aqueous-organic emulsionАрифуллинИ. Р.ArifullinI. R.

Нижний Новгород

i-arifullin@mail.ruКазанцевО. А.KazantsevO. A.

Нижний Новгород

СавиноваМ. В.SavinovaM. V.

Нижний Новгород

ЛаптеваЕ. А.LaptevaE. A.

Нижний Новгород

КомаровВ. А.KomarovV. A.

Нижний Новгород

ЧубенкоМ. Н.ChubenkoM. N.

Нижний Новгород

Нижегородский государственный технический университет им. Р.Е. АлексееваРоссияNizhny Novgorod State Technical University n.a. R.E. AlekseevRussian Federation20232607202315-64852Copyright © Арифуллин И.Р., Казанцев О.А., Савинова М.В., Лаптева Е.А., Комаров В.А., Чубенко М.Н., 20232023Арифуллин И.Р., Казанцев О.А., Савинова М.В., Лаптева Е.А., Комаров В.А., Чубенко М.Н.Arifullin I.R., Kazantsev O.A., Savinova M.V., Lapteva E.A., Komarov V.A., Chubenko M.N.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://www.plastics-news.ru/jour/article/view/888

Выявлено ускоряющее влияние добавок низкомолекулярного сульфокислотного ПАВ (алкилбензолсульфокислоты) и неионогенных или содержащих сульфокислотные звенья амфифильных сополимеров метокси- и высших алкоксиолиго(этиленгликоль)метакрилатов на синтез по реакции Манниха перспективного катионного мономера – N-(дибутиламинометил)метакриламида, протекающий в водно-аминной эмульсии. Показано влияние на каталитический эффект концентрации добавок и строения сополимеров.

The accelerating effect of adding a low molecular weight sulfonic acid surfactant (alkylbenzenesulfonic acid) and nonionic or containing sulfonic acid units amphiphilic copolymers of methoxy- and higher alkoxyoligo(ethylene glycol)methacrylates on the synthesis of a promising cationic monomer, N-(dibutylaminomethyl)methacrylamide, proceeding in an aqueous-amine emulsion, by the Mannich reaction, was revealed. The infl uence of the concentration of additives and the structure of copolymers on the catalytic effect is shown.

реакция МаннихаN-(дибутиламинометил)акриламидсинтезэмульсиякатализалкилбензолсульфокислотаамфифильные сополимерыалкоксиолиго(этиленгликоль)метакрилаты2-(акриламидо)додекансульфокислотаMannich reactionN-(dibutylaminomethyl)acrylamidesynthesisemulsioncatalysisalkylbenzenesulfonic acidamphiphilic copolymersalkoxyoligo(ethylene glycol)methacrylates2-(acrylamido)dodecanesulfonic acidПроведенные исследования сульфосодержащих полимеров проведены при финансовой поддержке Российского научного фонда в рамках выполнения проекта № 21-73-00271ReferencesHubbe, M.A. Prospects for Maintaining Strength of Paper and Paperboard Products While Using Less Forest Resources: A Review / M.A. Hubbe // BioResources. – 2013. – Vol. 9, N 1. – P. 1634–1763.Hubbe, M.A. Prospects for Maintaining Strength of Paper and Paperboard Products While Using Less Forest Resources: A Review / M.A. Hubbe // BioResources. – 2013. – Vol. 9, N 1. – P. 1634–1763.Li, S. Flocculating and dewatering performance of hydrophobic and hydrophilic solids using a thermal-sensitive copolymer. Water Science and Technology / S. Li, Y. Liao, G. Li // Wat. Sci. Tech. – 2017. Vol. 76, N 3. – P. 694–704.Li, S. Flocculating and dewatering performance of hydrophobic and hydrophilic solids using a thermal-sensitive copolymer. Water Science and Technology / S. Li, Y. Liao, G. Li // Wat. Sci. Tech. – 2017. Vol. 76, N 3. – P. 694–704.Kazantsev, O.A. Dependence of efficiency of polyalkyl acrylatebased pour point depressants on composition of crude oil / O.A. Kazantsev, I.R. Arifullin, A.A. Moikin et al. // Egypt. J. of Pet. – 2021. Vol. 30, N3. – P. 21–26.Kazantsev, O.A. Dependence of efficiency of polyalkyl acrylatebased pour point depressants on composition of crude oil / O.A. Kazantsev, I.R. Arifullin, A.A. Moikin et al. // Egypt. J. of Pet. – 2021. Vol. 30, N3. – P. 21–26.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. // Reaction Chemistry & Engineering. – 2020. – Vol. 5, N9. – P. 1791–1797.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. // Reaction Chemistry & Engineering. – 2020. – Vol. 5, N9. – P. 1791–1797.Khan, M.N. Micellar Catalysis / M.N. Khan // Surfactant Science Series. – 2007. – Vol. 133. – P. 504.Khan, M.N. Micellar Catalysis / M.N. Khan // Surfactant Science Series. – 2007. – Vol. 133. – P. 504.Sorella, G. Recent advances in catalysis in micellar media / G. Sorella, G. Strukul, A. Scarso // Green Chem. – 2015. – Vol. 17, N2. – P. 644–683.Sorella, G. Recent advances in catalysis in micellar media / G. Sorella, G. Strukul, A. Scarso // Green Chem. – 2015. – Vol. 17, N2. – P. 644–683.Березин, И.В. Физико-химические основы мицеллярного катализа / И.В. Березин, К. Мартинек, А.К. Яцимирский // Успехи химии. – 1973. – Т. 42, №10. – С. 1729–1756.Березин, И.В. Физико-химические основы мицеллярного катализа / И.В. Березин, К. Мартинек, А.К. Яцимирский // Успехи химии. – 1973. – Т. 42, №10. – С. 1729–1756.Blicke, F.F. The Mannich Reaction / F.F. Blicke // Organic Reactions. – 2011. Vol. 1. – P. 303–341.Blicke, F.F. The Mannich Reaction / F.F. Blicke // Organic Reactions. – 2011. Vol. 1. – P. 303–341.Tramontini, М. Further advances in the chemistry of Mannich bases / М. Tramontini, L. Angiolini // Tetrahedron. – 1990. – Vol. 46, N6. – P. 1791–1837.Tramontini, М. Further advances in the chemistry of Mannich bases / М. Tramontini, L. Angiolini // Tetrahedron. – 1990. – Vol. 46, N6. – P. 1791–1837.Roman, G. Mannich bases in medicinal chemistry and drug design / G. Roman // Eur. J. Med. Chem. – 2015. – Vol. 89. – P. 743–816.Roman, G. Mannich bases in medicinal chemistry and drug design / G. Roman // Eur. J. Med. Chem. – 2015. – Vol. 89. – P. 743–816.Laschewsky, A. Molecular Concepts, Self-Organisation and Properties of Polysoaps / A. Laschewsky // Adv. Polym. Sci. – 1995. – Vol. 124. – Р. 1–86.Laschewsky, A. Molecular Concepts, Self-Organisation and Properties of Polysoaps / A. Laschewsky // Adv. Polym. Sci. – 1995. – Vol. 124. – Р. 1–86.Pashirova, T.N. Self Assembled Quaternary Ammonium Containing Comb-Like Polyelectrolytes for the Hydrolysis of Organophosphorous Esters: Effect of Head Groups and Counter-Ions / T.N. Pashirova, P.A. Fetin, M.V. Kadnikov et al. // ChemPlusChem. – 2020. – Vol. 85. – P. 1939–1948.Pashirova, T.N. Self Assembled Quaternary Ammonium Containing Comb-Like Polyelectrolytes for the Hydrolysis of Organophosphorous Esters: Effect of Head Groups and Counter-Ions / T.N. Pashirova, P.A. Fetin, M.V. Kadnikov et al. // ChemPlusChem. – 2020. – Vol. 85. – P. 1939–1948.Vancoillie, G. Thermoresponsive poly(oligo ethylene glycol acrylates) / G. Vancoillie, D. Frank, R. Hoogenboom // Prog. Polym. Sci. – 2014. – Vol. 39, N6. – P. 1074–1095.Vancoillie, G. Thermoresponsive poly(oligo ethylene glycol acrylates) / G. Vancoillie, D. Frank, R. Hoogenboom // Prog. Polym. Sci. – 2014. – Vol. 39, N6. – P. 1074–1095.Matsumoto, M. Self-assembly of amphiphilic block pendant polymers as microphase separation materials and folded flower micelles / M. Matsumoto, M. Takenaka, M. Sawamoto, T. Terashima / Polym Chem. – 2019. – Vol. 10, N 36. – P. 4954–4961.Matsumoto, M. Self-assembly of amphiphilic block pendant polymers as microphase separation materials and folded flower micelles / M. Matsumoto, M. Takenaka, M. Sawamoto, T. Terashima / Polym Chem. – 2019. – Vol. 10, N 36. – P. 4954–4961.Kamorin, D.M. Synthesis and thermoresponsive prop erties of polymethacrylate molecular brushes with oligo(ethylene glycol)- block-oligo(propylene glycol) side chains / D.M. Kamorin, A.S. Simagin, D.V. Orekhov et al. // Polymer Bulletin. – 2021. – Vol. 78. – P. 8599–8616.Kamorin, D.M. Synthesis and thermoresponsive prop erties of polymethacrylate molecular brushes with oligo(ethylene glycol)- block-oligo(propylene glycol) side chains / D.M. Kamorin, A.S. Simagin, D.V. Orekhov et al. // Polymer Bulletin. – 2021. – Vol. 78. – P. 8599–8616.Sivokhin, A. Random and Diblock Thermoresponsive OEGMA-based Copolymers Synthesized via Photo-Induced RAFT Polymerization / A. Sivokhin, D. Orekhov, O. Kazantsev et. al // Polymers. – 2022. – Vol. 14. P. 137.Sivokhin, A. Random and Diblock Thermoresponsive OEGMA-based Copolymers Synthesized via Photo-Induced RAFT Polymerization / A. Sivokhin, D. Orekhov, O. Kazantsev et. al // Polymers. – 2022. – Vol. 14. P. 137.Hattori, G. Self-assembly of PEG/dodecyl-graft amphiphilic copolymers in water: consequences of the monomer sequence and chain flexibility on uniform micelles./ G. Hattori, Y. Hirai, M. Sawamoto, T. Terashima // Polym Chem. – 2017. – Vol.8, N 46. – P. 7248–7259.Hattori, G. Self-assembly of PEG/dodecyl-graft amphiphilic copolymers in water: consequences of the monomer sequence and chain flexibility on uniform micelles./ G. Hattori, Y. Hirai, M. Sawamoto, T. Terashima // Polym Chem. – 2017. – Vol.8, N 46. – P. 7248–7259.Sivokhin, A.Р. Amphiphilic thermo-responsive copolymer brushes: synthesis, characterization and self-assembly into flower-like micelles / A.Р. Sivokhin, D.V. Orekhov, O.A. Kazantsev et al. // Polymer Journal. – 2021. – Vol. 53, N5. – P. 655–665.Sivokhin, A.Р. Amphiphilic thermo-responsive copolymer brushes: synthesis, characterization and self-assembly into flower-like micelles / A.Р. Sivokhin, D.V. Orekhov, O.A. Kazantsev et al. // Polymer Journal. – 2021. – Vol. 53, N5. – P. 655–665.Terashima, T. Single-Chain Nanoparticles via Self-Folding Amphiphilic Copolymers in Water / T. Terashima, M. Sawamoto // Single-Chain Polymer Nanoparticles. – 2017. – P. 313–339.Terashima, T. Single-Chain Nanoparticles via Self-Folding Amphiphilic Copolymers in Water / T. Terashima, M. Sawamoto // Single-Chain Polymer Nanoparticles. – 2017. – P. 313–339.Frisch, H. Macromolecular Superstructures: A Future Beyond Single Chain Nanoparticles / H. Frisch, B. T. Tuten, C. Barner-Kowollik // Isr. J. Chem. – 2020. – V. 60 – P. 1–15.Frisch, H. Macromolecular Superstructures: A Future Beyond Single Chain Nanoparticles / H. Frisch, B. T. Tuten, C. Barner-Kowollik // Isr. J. Chem. – 2020. – V. 60 – P. 1–15.Terashima, T. Synthesis and Single-Chain Folding of Amphiphilic Random Copolymers in Water / T. Terashima, T. Sugita, K. Fukae, M. Sawamoto // Macromolecules. – 2014. – V. 47. – P. 589−600.Terashima, T. Synthesis and Single-Chain Folding of Amphiphilic Random Copolymers in Water / T. Terashima, T. Sugita, K. Fukae, M. Sawamoto // Macromolecules. – 2014. – V. 47. – P. 589−600.Rubio-Cervilla, J. Advances in Single-Chain Nanoparticles for Catalysis Applications / J. Rubio-Cervilla, E. González, J. Pomposo // Nanomaterials. – 2017. – Vol. 7, N10. – P. 341–361.Rubio-Cervilla, J. Advances in Single-Chain Nanoparticles for Catalysis Applications / J. Rubio-Cervilla, E. González, J. Pomposo // Nanomaterials. – 2017. – Vol. 7, N10. – P. 341–361.Rothfuss, H. Single-Chain Nanoparticles as Catalytic Nanoreactors / H. Rothfuss, N.D. Knöfel, P.W. Roesky, C. Barner-Kowollik // JACS. – 2018. – Vol. 140, N18. – P. 5875–5881.Rothfuss, H. Single-Chain Nanoparticles as Catalytic Nanoreactors / H. Rothfuss, N.D. Knöfel, P.W. Roesky, C. Barner-Kowollik // JACS. – 2018. – Vol. 140, N18. – P. 5875–5881.Artar, M. Catalysis Inside Folded Single Macromolecules in Water / M. Artar, A.R. Palmans // Effects of Nanoconfinement on Catalysis, Fundamental and Applied Catalysis. – 2017. – P. 105–123.Artar, M. Catalysis Inside Folded Single Macromolecules in Water / M. Artar, A.R. Palmans // Effects of Nanoconfinement on Catalysis, Fundamental and Applied Catalysis. – 2017. – P. 105–123.Симагин, А.С. Амино- и сульфосодержащие молекулярные щетки на основе олигоэтиленгликоль(мет)акрилатов – синтез и свойства в растворах / А.С. Симагин, М.В. Савинова, Д.М. Каморин и др. // Высокомолекулярные соединения. – 2022. – Т. 64. – №2. – С. 251–264.Симагин, А.С. Амино- и сульфосодержащие молекулярные щетки на основе олигоэтиленгликоль(мет)акрилатов – синтез и свойства в растворах / А.С. Симагин, М.В. Савинова, Д.М. Каморин и др. // Высокомолекулярные соединения. – 2022. – Т. 64. – №2. – С. 251–264.Орехов, Д.В. Амфифильные свойства алкоксиолигоэтиленгликольметакрилатов и сополимеров на их основе / Д.В. Орехов, К.В. Ширшин, М.В. Савинова и др. // Пластические массы. – 2019. – №7–8. – С. 38–41.Орехов, Д.В. Амфифильные свойства алкоксиолигоэтиленгликольметакрилатов и сополимеров на их основе / Д.В. Орехов, К.В. Ширшин, М.В. Савинова и др. // Пластические массы. – 2019. – №7–8. – С. 38–41.

The authors declare that there are no conflicts of interest present.