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Unconventional method used in synthesis of polyphosphoesters

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Abstract

Polyphosphonates, polyphosphates, polyarylazophosphonates and polyarylazophosphates were synthesized by a new alternative to the classical phase transfer catalysis, respectively, the modified inverse phase transfer catalysis (IPTC) polycondensation of various phenylphosphonic (phosphoric) dichlorides (phenylphosphonic dichloride, phenylphosphoric dichloride, p-chlorophenylphosphoric dichloride) with bisphenols: bisphenol A, tetrabromobisphenol A, bis-(4-hydroxyphenyl)methane (bisphenol F), 4,4′-dihydroxyazobenzene. The polymers were characterized by infrared spectroscopy and magnetic resonance (1H-NMR, 31P-NMR, 13C-NMR) spectroscopy. Yields in the range of 63.5–85% and molecular weights (M w) of ~2,000–8,200 g mol−1 were obtained. Polyphosphonates were stable up 210–270 °C and polyphosphates up 190–220 °C in air atmosphere. For a correct estimation of the thermal behavior of similar compounds, a kinetic analysis using a modified version of Non Parametric Kinetic method for representative polyphosphonate and polyphosphate was realized. The studies made on the hydrolytic degradation of the synthesized polyphosphates show that the most stable polymer under alkali-catalyzed degradation is the polyphosphate obtained by IPTC of phenylphosphoric dichloride and bisphenol A.

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Acknowledgments

This study was financially supported by CNCSIS GR 94/2008. The authors are grateful to Professor Stefan Berger, Institute for Analytical Chemistry, Leipzig for providing access to the NMR spectrometer and Dr. Ecaterina Avram, Petru Poni Institute of Macromolecular Chemistry, Iasi, for molecular weights determination.

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Authors and Affiliations

  1. Institute of Chemistry, Romanian Academy, 24 Mihai Viteazul Bvd., 300223, Timisoara, Romania

    Smaranda Iliescu, Aurelia Pascariu, Nicoleta Plesu, Adriana Popa, Lavinia Macarie & Gheorghe Ilia

  2. Faculty of Chemistry-Biology and Geography, West University, 116 Pestalozzi Str., 300115, Timisoara, Romania

    Gheorghe Ilia

Authors
  1. Smaranda Iliescu
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  2. Aurelia Pascariu
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  3. Nicoleta Plesu
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  4. Adriana Popa
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  5. Lavinia Macarie
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  6. Gheorghe Ilia
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Correspondence to Gheorghe Ilia.

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Iliescu, S., Pascariu, A., Plesu, N. et al. Unconventional method used in synthesis of polyphosphoesters. Polym. Bull. 63, 485–495 (2009). https://doi.org/10.1007/s00289-009-0107-2

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  • DOI: https://doi.org/10.1007/s00289-009-0107-2

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