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Spectroscopic studies of a ring opening process between epoxy- and aminosilanes and imine formation reactions in aqueous solutions

  • Original Paper: Sol-gel, hybrids and solution chemistries
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Abstract

NMR and Raman spectroscopy studies were performed for different 3-aminopropyl(trimethoxy)- and 3-glycidoxypropyl(trimethoxy)silane based sol-gel systems containing different ketones. Exceptionally stable imine products were obtained depending on a reaction system at alkaline pH conditions and in the presence of water. These imine formation reactions were carried out without further catalyst. In addition, effect of water for the epoxy ring opening process was demonstrated, as well as the effect of solvents for the reaction path was confirmed.

The reaction between 3-aminopropyl(trimethoxy)- and 3-glycidoxypropyl(trimethoxy)silane needs additional catalyst to proceed fast or the reaction between the organic parts remains very slow. In case of isopropyl alcohol as the solvent, the result is the same. Water catalyses the organic and hydrolysation/condensation reactions. Ketones, like acetone initiates stable imine formation and water as a by-product methoxy group hydrolysation, but the epoxy groups remains unchanged after long period

Highlights

  • Stable organosiloxane based imines were synthesised in the presence of water as a by-product and in a very alkaline conditions (pH ≥ 12).

  • Synthesised and characterised amine/epoxy/ketone – sol-gel one-pot systems proved that ketones and amines form imines, as was expected, and these imines showed to be very stable in aqueous solutions and no drying agents, extraction or precursors having aromatic substituents were used during the syntheses.

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Acknowledgements

Research presented here were partially supported by the VTT – Technical Research Center of Finland and by the Gdańsk University of Technology (DS project of the Faculty of ETI). This article is also based upon work from COST Action “Raman-based applications for clinical diagnostics – Raman4Clinics” (BM 1401), supported by COST (European Cooperation in Science and Technology).

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Authors and Affiliations

  1. VTT Technical Research Centre of Finland Ltd, Kaitoväylä 1, P.O. Box 1100, FI-90571, Oulu, Finland

    Mikko Keränen, Arto Maaninen & Tiina Maaninen

  2. Department of Metrology and Optoelectronics, Gdańsk University of Technology, ul. Narutowicza 11/12, 80-233, Gdańsk, Poland

    Marcin Gnyba

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  1. Mikko Keränen
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  2. Arto Maaninen
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  3. Marcin Gnyba
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  4. Tiina Maaninen
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Correspondence to Mikko Keränen.

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Keränen, M., Maaninen, A., Gnyba, M. et al. Spectroscopic studies of a ring opening process between epoxy- and aminosilanes and imine formation reactions in aqueous solutions. J Sol-Gel Sci Technol 87, 725–733 (2018). https://doi.org/10.1007/s10971-018-4758-z

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  • DOI: https://doi.org/10.1007/s10971-018-4758-z

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