Kinetics and Mechanism of Synthesis of Carboxyl-Containing N-Vinyl-2-Pyrrolidone Telehelics for Pharmacological Use
It was found that sulfanylethanoic and 3-sulfanylpropanoic acids are effective regulators of molecular weight with chain transfer constants of 0.441 and 0.317, respectively, and show an unexpected acceleration effect on the radical polymerization of N-vinyl-2-pyrrolidone, initiated by 2,2’-azobisiso...
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MDPI AG
2021-08-01
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| author | Andrey N. Kuskov Anna L. Luss Inessa A. Gritskova Mikhail I. Shtilman Mikhail V. Motyakin Irina I. Levina Anna M. Nechaeva Oksana Yu. Sizova Aristidis M. Tsatsakis Yaroslav O. Mezhuev |
| author_facet | Andrey N. Kuskov Anna L. Luss Inessa A. Gritskova Mikhail I. Shtilman Mikhail V. Motyakin Irina I. Levina Anna M. Nechaeva Oksana Yu. Sizova Aristidis M. Tsatsakis Yaroslav O. Mezhuev |
| author_sort | Andrey N. Kuskov |
| collection | DOAJ |
| description | It was found that sulfanylethanoic and 3-sulfanylpropanoic acids are effective regulators of molecular weight with chain transfer constants of 0.441 and 0.317, respectively, and show an unexpected acceleration effect on the radical polymerization of N-vinyl-2-pyrrolidone, initiated by 2,2’-azobisisobutyronitrile. It was determined for the first time that the thiolate anions of mercapto acids form a high-temperature redox initiating system with 2,2’-azobisisobutyronitrile during the radical polymerization of N-vinyl-2-pyrrolidone in 1,4-dioxane. Considering the peculiarities of initiation, a kinetic model of the polymerization of N-vinyl-2-pyrrolidone is proposed, and it is shown that the theoretical orders of the reaction rate, with respect to the monomer, initiator, and chain transfer agent, are 1, 0.75, 0.25, and are close to their experimentally determined values. Carboxyl-containing techelics of N-vinyl-2-pyrrolidone were synthesized so that it can slow down the release of the anticancer drug, doxorubicin, from aqueous solutions, which can find its application in the pharmacological field. |
| first_indexed | 2024-03-10T09:10:24Z |
| format | Article |
| id | doaj.art-af23d04fb7b04ac793034b003c8335ea |
| institution | Directory Open Access Journal |
| issn | 2073-4360 |
| language | English |
| last_indexed | 2024-03-10T09:10:24Z |
| publishDate | 2021-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Polymers |
| spelling | doaj.art-af23d04fb7b04ac793034b003c8335ea2023-11-22T06:04:52ZengMDPI AGPolymers2073-43602021-08-011315256910.3390/polym13152569Kinetics and Mechanism of Synthesis of Carboxyl-Containing N-Vinyl-2-Pyrrolidone Telehelics for Pharmacological UseAndrey N. Kuskov0Anna L. Luss1Inessa A. Gritskova2Mikhail I. Shtilman3Mikhail V. Motyakin4Irina I. Levina5Anna M. Nechaeva6Oksana Yu. Sizova7Aristidis M. Tsatsakis8Yaroslav O. Mezhuev9Department of Biomaterials, Mendeleev University of Chemical Technology of Russia, 125047 Moscow, RussiaDepartment of Biomaterials, Mendeleev University of Chemical Technology of Russia, 125047 Moscow, RussiaDepartment of Chemistry and Technology of Macromolecular Compounds, MIREA—Russian Technological University (RTU MIREA), 119454 Moscow, RussiaDepartment of Biomaterials, Mendeleev University of Chemical Technology of Russia, 125047 Moscow, RussiaEmanuel Institute of Biochemical Physics, Russian Academy of Sciences, 119334 Moscow, RussiaEmanuel Institute of Biochemical Physics, Russian Academy of Sciences, 119334 Moscow, RussiaDepartment of Biomaterials, Mendeleev University of Chemical Technology of Russia, 125047 Moscow, RussiaDepartment of Biomaterials, Mendeleev University of Chemical Technology of Russia, 125047 Moscow, RussiaCenter of Toxicology Science & Research, Division of Morphology, Medical School, Voutes Campus, University of Crete, 71003 Heraklion, GreeceDepartment of Biomaterials, Mendeleev University of Chemical Technology of Russia, 125047 Moscow, RussiaIt was found that sulfanylethanoic and 3-sulfanylpropanoic acids are effective regulators of molecular weight with chain transfer constants of 0.441 and 0.317, respectively, and show an unexpected acceleration effect on the radical polymerization of N-vinyl-2-pyrrolidone, initiated by 2,2’-azobisisobutyronitrile. It was determined for the first time that the thiolate anions of mercapto acids form a high-temperature redox initiating system with 2,2’-azobisisobutyronitrile during the radical polymerization of N-vinyl-2-pyrrolidone in 1,4-dioxane. Considering the peculiarities of initiation, a kinetic model of the polymerization of N-vinyl-2-pyrrolidone is proposed, and it is shown that the theoretical orders of the reaction rate, with respect to the monomer, initiator, and chain transfer agent, are 1, 0.75, 0.25, and are close to their experimentally determined values. Carboxyl-containing techelics of N-vinyl-2-pyrrolidone were synthesized so that it can slow down the release of the anticancer drug, doxorubicin, from aqueous solutions, which can find its application in the pharmacological field.https://www.mdpi.com/2073-4360/13/15/2569N-vinyl-2-pyrrolidone polymerizationpolymerization mechanismpolymerization kineticsdoxorubicin |
| spellingShingle | Andrey N. Kuskov Anna L. Luss Inessa A. Gritskova Mikhail I. Shtilman Mikhail V. Motyakin Irina I. Levina Anna M. Nechaeva Oksana Yu. Sizova Aristidis M. Tsatsakis Yaroslav O. Mezhuev Kinetics and Mechanism of Synthesis of Carboxyl-Containing N-Vinyl-2-Pyrrolidone Telehelics for Pharmacological Use Polymers N-vinyl-2-pyrrolidone polymerization polymerization mechanism polymerization kinetics doxorubicin |
| title | Kinetics and Mechanism of Synthesis of Carboxyl-Containing N-Vinyl-2-Pyrrolidone Telehelics for Pharmacological Use |
| title_full | Kinetics and Mechanism of Synthesis of Carboxyl-Containing N-Vinyl-2-Pyrrolidone Telehelics for Pharmacological Use |
| title_fullStr | Kinetics and Mechanism of Synthesis of Carboxyl-Containing N-Vinyl-2-Pyrrolidone Telehelics for Pharmacological Use |
| title_full_unstemmed | Kinetics and Mechanism of Synthesis of Carboxyl-Containing N-Vinyl-2-Pyrrolidone Telehelics for Pharmacological Use |
| title_short | Kinetics and Mechanism of Synthesis of Carboxyl-Containing N-Vinyl-2-Pyrrolidone Telehelics for Pharmacological Use |
| title_sort | kinetics and mechanism of synthesis of carboxyl containing n vinyl 2 pyrrolidone telehelics for pharmacological use |
| topic | N-vinyl-2-pyrrolidone polymerization polymerization mechanism polymerization kinetics doxorubicin |
| url | https://www.mdpi.com/2073-4360/13/15/2569 |
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