Synthesis and characterization of new biodegradable gels based on 2,2 '-(ethylenedioxy) diethanethiol and pentaerythritol triacrylate

Authors

  • R. Shulen al-Farabi Kazakh National University
  • D. Kazybayeva al-Farabi Kazakh National University

DOI:

https://doi.org/10.31643/2022/6445.03

Keywords:

2,2 '-(ethylenedioxy)diethanethiol, pentaerythritol triacrylate, gel, biodegradation, thiol-ene "click" polymerization.

Abstract

The work is devoted to the synthesis and characterization of gels based on the monomers pentaerythritol triaacrylate (PETriA) and 2,2 '-(ethylenedioxy)diethanethiol (EDODET) by thiol-ene "click" polymerization. The properties of the obtained gels were investigated by IR, Raman spectroscopy, mechanical analysis. Sol-gel analysis of obtained networks was carried out and the degradability was investigated. The results of IR spectroscopy confirmed the presence of -C = O and -C-O-C- groups in the composition of the obtained gels. The presence of unreacted C = C bonds conjugated with C = O, as well as thiol groups, varies depending on the composition of the initial monomer mixture (IMM). Raman spectroscopy results correlate well with IR data. Raman spectra also show C-S, S-S and SH characteristic bands that are difficult to identify by IR spectroscopy. It was found that the composition of MM affects the physicochemical properties of the synthesized gels. The highest yield of the gel fraction of obtained polymers was found in samples with an equimolar composition of IMM. The analysis of mechanical properties showed that gels with an excess of PETriA exhibit more elastic properties, and an excess of EDODET leads to the formation of networks with a higher crosslinking density. The study of the ability of obtained PETria-EDODET gels to degrade in a 3% solution of hydrogen peroxide showed that the polymer network degrades by 12% within 60 days. This property of the obtained gels can find application in the creation of targeted drug delivery systems with their prolonged release.

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Author Biographies

R. Shulen, al-Farabi Kazakh National University

MSc

D. Kazybayeva , al-Farabi Kazakh National University

MSc, PhD studen

References

Lowe AB.Thiol-ene “click” reactions and recent applications in polymer and materials synthesis.Polym. Chem. 2010;1(1):17–36. https://doi.org/10.1039/B9PY00216B

Machado TO, Sayer C, Araujo PHH.Thiol-ene polymerisation: A promising technique to obtain novel biomaterials.Eur. Polym. J. 2017;86:200–215. https://doi.org/10.1016/j.eurpolymj.2016.02.025

Carlborg CF.et al.Beyond PDMS: off-stoichiometry thiol–ene (OSTE) based soft lithography for rapid prototyping of microfluidic devices.Lab Chip. 2011;11(18):3136. https://doi.org/10.1039/C1LC20388F

Bernkop-Schnürch A, Greimel A.Thiomers: The next generation of mucoadhesive polymers.Am. J. Drug Deliv. 2005;3:141–154. https://doi.org/10.1016/j.addr.2005.07.002[

Kloxin AM.Thiol–ene click hydrogels for therapeutic delivery. ACS Biomater. Sci. Eng.2016;2(2):165–179. https://doi.org/10.1021/acsbiomaterials.5b00420

Hoyle CE, Bowman CN.Thiol-ene click chemistry.Angew. Chemie -Int. Ed. 2010;49(9):1540–1573. https://doi.org/10.1002/anie.200903924

Summonte S.et al.Thiolated polymeric hydrogels for biomedical application: Cross-linking mechanisms.J. Control. Release.2021;330:470–482. https://doi.org/10.1016/j.jconrel.2020.12.037

Lüchow M, Fortuin L, Malkoch M.Modular, synthetic, thiol-ene mediated hydrogel networks as potential scaffolds for 3D cell cultures and tissue regeneration.J. Polym. Sci. 2020;58(22):3153–3164. https://doi.org/10.1002/pol.20200530

Tamariz E, Rios-ramírez A.Biodegradation of medical purpose polymeric materials and their impact on biocompatibility.IntechOpen;2013. Chapter 1, Biodegradation -Life of Science, pp.3–30. https://doi.org/10.5772/56220

Kamath KR, Park K.Biodegradable hydrogels in drug delivery. Advanced Drug Delivery Reviews.1993;11:59–84. https://doi.org/10.1016/0169-409X(93)90027-2

Kazitsyna LA,Kupletskaya NB. Primenenie UF-, IK-, YaMR-i mass-spektroskopii v organicheskoy khimii(Application of UV, IR and NMR spectroscopy in organic chemistry).Moscow: Izdatelstvo Moskovskogo Universiteta. 1979,237.(in Russian)

Wittman C, Chockley P, Singh SK. Pase L, Lieschke GJ,Grabher C.Hydrogen peroxide in inflammation: messenger, guide, and assassin. Advances in Hematology. 2012;2012:1–6. https://doi.org/10.1155/2012/541471

UlbrichtU, JordanR, LuxenhoferR. On the biodegradability of polyethylene glycol, polypeptoids and poly(2-oxazoline)s.Biomaterials.2014;35(17):4848-4861. https://doi.org/10.1016/j.biomaterials.2014.02.029

Nair LS, Laurencin CT. Biodegradable polymers as biomaterials.Prog. Polym. Sci.2007;32:762–798. https://doi.org/10.1016/j.progpolymsci.2007.05.017

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Published

2021-11-30

How to Cite

Shulen, R., & Kazybayeva , D. (2021). Synthesis and characterization of new biodegradable gels based on 2,2 ’-(ethylenedioxy) diethanethiol and pentaerythritol triacrylate . Kompleksnoe Ispolzovanie Mineralnogo Syra = Complex Use of Mineral Resources, 320(1), 25–31. https://doi.org/10.31643/2022/6445.03