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Carbalkoxilation of polyethylene polyamines with dialkyl carbonates

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Abstract

The reaction of carbalkoxylation of polyethylene polyamines (PEPA) with various dialkyl carbonates, including fluorine-containing ones, was studied in order to obtain new hardeners for epoxy resins containing a carbamate functional group in the side chain. The degree of functionalization of PEPA decreases with an increase in the length of the hydrocarbon radical in the carbonate. The maximum degree of carbalkoxylation was achieved using ethyl (2,2,3,3-tetrafluoropropyl) carbonate. The obtained PEPA O-alkyl carbamates demonstrated catalytic activity in the curing reaction of ED-20 epoxy resin. The highest reactivity was exhibited by O-ethyl carbamate of PEPA. The onset temperature of curing in this case was 55 °C with a total degree of carbethoxylation of 12%.

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Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 ul. S. Kovalevskoj, 620137, Yekaterinburg, Russian Federation

    A. M. Semenova, N. A. Malenkih, E. F. Zhilina, A. V. Mekhaev & A. V. Pestov

  2. First President of Russia B. N. Yeltsin Ural Federal University, 19 ul. Mira, 620002, Yekaterinburg, Russian Federation

    N. A. Malenkih & A. V. Pestov

Authors
  1. A. M. Semenova
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  2. N. A. Malenkih
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  3. E. F. Zhilina
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  4. A. V. Mekhaev
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  5. A. V. Pestov
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Correspondence to A. M. Semenova.

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Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 90th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 146–151, January, 2022.

The work was carried out within the framework of the State assignment of the I. Ya. Postovsky Institute of Organic Synthesis, the Ural Branch of the Russian Academy of Sciences (themes No. AAAA-A19-119012290116-9 and No. AAAA-A19-119012490006-1) using the equipment of the Shared Use Center “Spectroscopy and Analysis of Organic Compounds”.

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Semenova, A.M., Malenkih, N.A., Zhilina, E.F. et al. Carbalkoxilation of polyethylene polyamines with dialkyl carbonates. Russ Chem Bull 71, 146–151 (2022). https://doi.org/10.1007/s11172-022-3388-3

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  • DOI: https://doi.org/10.1007/s11172-022-3388-3

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