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Polymers 2018, 10(7), 740; https://doi.org/10.3390/polym10070740

One-Pot Synthesis of P(O)-N Containing Compounds Using N-Chlorosuccinimide and Their Influence in Thermal Decomposition of PU Foams

1
Additives and Chemistry Group, Advanced Fibers, Empa—Swiss Federal Laboratories for Materials Science and Technology, Lerchenfeldstrasse 5, 9014 St. Gallen, Switzerland
2
Laboratory for Functional Polymers, Empa—Swiss Federal Laboratories for Materials Science and Technology, Überlandstrasse 129, 8600 Dübendorf, Switzerland
*
Authors to whom correspondence should be addressed.
Received: 30 May 2018 / Revised: 28 June 2018 / Accepted: 3 July 2018 / Published: 5 July 2018
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Abstract

Synthesis of intermediate containing P(O)-Cl bonds is the key to converting P(O)-H bonds to P(O)-N. In this work we have performed chlorination reactions of different H-phosphinates and H-phosphonates using N-chlorosuccinimide as an environmentally-benign chlorinating agent. The chlorination reaction showed high yield and high selectivity for transformation of P(O)-H bonds into P(O)-Cl analogues, resulting in an easily separable succinimide as the by-product. Using a one-pot synthesis methodology, we have synthesized a series of P(O)-N containing derivatives whose synthesis was found to be dependent on the reaction solvents and the starting materials. The synthesized P(O)-N compounds were incorporated in flexible polyurethane foam (FPUF) and screened for their influence in thermal decomposition of FPUFs using thermogravimetric analysis (TGA) and a microscale combustion calorimeter (MCC). All solid P(O)-N compounds influenced the first-stage decomposition of FPUFs, which resulted in an accelerated decomposition or temporary stabilization of this stage. However, the liquid P(O)-N derivatives volatilize at an earlier stage and could be active in the gas phase. In addition, they also work in condensed phase via acid catalyzed decomposition for FPUFs. View Full-Text
Keywords: chlorination reaction; phosphoramidates; phosphonamidates; thermal decomposition; polyurethane foams chlorination reaction; phosphoramidates; phosphonamidates; thermal decomposition; polyurethane foams
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Salmeia, K.A.; Flaig, F.; Rentsch, D.; Gaan, S. One-Pot Synthesis of P(O)-N Containing Compounds Using N-Chlorosuccinimide and Their Influence in Thermal Decomposition of PU Foams. Polymers 2018, 10, 740.

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