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Volume 14
Issue 24
10.3390/polym14245481
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Article

Aminolysis of Poly-3-Hydroxybutyrate in N,N-Dimethylformamide and 1,4-Dioxane and Formation of Functionalized Oligomers

by
Anatoly Nikolayevich Boyandin
1,2,*,
Viktoriya Aleksandrovna Bessonova
3,
Natalya Leonidovna Ertiletskaya
1,2,
Anna Alekseevna Sukhanova
1,
Taisiya Aleksandrovna Shalygina
1 and
Alexander Alexandrovich Kondrasenko
4
1
Scientific Laboratory “Smart Materials and Structures”, Reshetnev Siberian State University of Science and Technology, 433/1 Ul. Semafornaya, Krasnoyarsk 660059, Russia
2
Institute of Biophysics SB RAS, Federal Research Center “Krasnoyarsk Science Center of the Siberian Branch of the Russian Academy of Sciences”, 50, b. 50, Akademgorodok, Krasnoyarsk 660036, Russia
3
School of Fundamental Biology and Biotechnology, Siberian Federal University, 79 Svobodny pr., Krasnoyarsk 660041, Russia
4
Institute of Chemistry and Chemical Technology SB RAS, Federal Research Center “Krasnoyarsk Science Center of the Siberian Branch of the Russian Academy of Sciences”, 50, b. 24, Akademgorodok, Krasnoyarsk 660036, Russia
*
Author to whom correspondence should be addressed.
Polymers 2022, 14(24), 5481; https://doi.org/10.3390/polym14245481
Submission received: 31 October 2022 / Revised: 8 December 2022 / Accepted: 11 December 2022 / Published: 14 December 2022
(This article belongs to the Special Issue Biodegradable Polyesters: Synthesis, Properties, Applications)
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Abstract

The degradation pattern of bacterial poly-3-hydroxybutyrate (PHB) in dimethylformamide (DMF) and dioxane solutions at 100 °C assisted by ethylenediamine, 1,4-diaminobutane and monoaminoethanol was studied. When diamines were introduced into the PHB solution in DMF in the amount of 1 mol of the reagent to 5 or 10 mol of PHB monomers, a rapid decrease in the molecular weight of the polymer was observed. The initial value of the weight average molecular weight (Mw) 840 kDa had decreased by 20–30 times within the first 10–20 min of the experiment, followed by its gradual decrease to several thousand Da. When a similar molar quantity of aminoethanol was added, the molecular weight decreased slower. PHB had been degrading much slower in the dioxane solution than in DMF. By varying the number of reagents, it was possible to reach stabilization of the Mw at 1000–3000 Da when using diamines and 8000–20,000 Da using aminoethanol. 1H NMR analysis of the oligomers revealed of amino and amido groups forming in their structure. From the opposite end of the polymer chain, residues of 3-hydroxybutyric, crotonic and isocrotonic acids were formed during degradation. Differential scanning calorimetry indicated that after oligomerization there was a decrease in the melting point from 178 °C to 140–170 °C depending on the decrease in the molecular weight. The method proposed can be used for obtaining aminated PHB oligomers.
Keywords: poly-3-hydroxybutyrate; polyesters; bifunctional amines; aminolysis; functionalized oligomers poly-3-hydroxybutyrate; polyesters; bifunctional amines; aminolysis; functionalized oligomers
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MDPI and ACS Style

Boyandin, A.N.; Bessonova, V.A.; Ertiletskaya, N.L.; Sukhanova, A.A.; Shalygina, T.A.; Kondrasenko, A.A. Aminolysis of Poly-3-Hydroxybutyrate in N,N-Dimethylformamide and 1,4-Dioxane and Formation of Functionalized Oligomers. Polymers 2022, 14, 5481. https://doi.org/10.3390/polym14245481

AMA Style

Boyandin AN, Bessonova VA, Ertiletskaya NL, Sukhanova AA, Shalygina TA, Kondrasenko AA. Aminolysis of Poly-3-Hydroxybutyrate in N,N-Dimethylformamide and 1,4-Dioxane and Formation of Functionalized Oligomers. Polymers. 2022; 14(24):5481. https://doi.org/10.3390/polym14245481

Chicago/Turabian Style

Boyandin, Anatoly Nikolayevich, Viktoriya Aleksandrovna Bessonova, Natalya Leonidovna Ertiletskaya, Anna Alekseevna Sukhanova, Taisiya Aleksandrovna Shalygina, and Alexander Alexandrovich Kondrasenko. 2022. "Aminolysis of Poly-3-Hydroxybutyrate in N,N-Dimethylformamide and 1,4-Dioxane and Formation of Functionalized Oligomers" Polymers 14, no. 24: 5481. https://doi.org/10.3390/polym14245481

APA Style

Boyandin, A. N., Bessonova, V. A., Ertiletskaya, N. L., Sukhanova, A. A., Shalygina, T. A., & Kondrasenko, A. A. (2022). Aminolysis of Poly-3-Hydroxybutyrate in N,N-Dimethylformamide and 1,4-Dioxane and Formation of Functionalized Oligomers. Polymers, 14(24), 5481. https://doi.org/10.3390/polym14245481

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