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Correlations of limiting oxygen index with structural polyphosphoester features by QSPR approaches

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Abstract

Fire retardant materials diminish the hazard to life from fire. Polyphosphonates and polyphosphates display good flame retardancy and attractive plasticizing properties, being an important class of organophosphorus based polymer additives. Properties of previously synthesized polyphosphoesters are presented here, being simulated as monomers. In this quantitative structure–property relationship work, the flammability was expressed by limiting oxygen index (LOI) values, which were determined experimentally. Two types of chiral structures were found by molecular mechanics calculations using the MMFF94s force field for half of the monomers, consequently, two datasets were built. Structural parameters were calculated for the minimum energy structures and were related to the LOI values by multiple linear regression (MLR), artificial neural networks (ANNs), and support vector machines (SVMs). MLR calculations were combined with a genetic algorithm for variable selection. Stable and predictive MLR models in terms of 2D autocorrelation parameters weighed by atomic polarizabilities and of 3D-Morse descriptors were obtained. Somewhat inferior fits were found in the nonlinear modeling by ANNs and SVMs with the same set of descriptors. Monomers including R chiral structures gave more stable and predictive models compared to the S isomers in all approaches. Monomer geometry influences the flame retardancy, being favorable for R isomers.

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Acknowledgments

This project was financially supported by Project 1.1 of the Institute of Chemistry Timisoara of the Romanian Academy. The authors are indebted to Chemaxon Ltd., OpenEye Ltd. and Prof. Paola Gramatica from The University of Insubria (Varese, Italy) for giving access to their software.

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Authors and Affiliations

  1. Institute of Chemistry, Timisoara of the Romanian Academy, B-dul Mihai Viteazul 24, 300223, Timişoara, Romania

    Simona Funar-Timofei & Smaranda Iliescu

  2. Natural Science Laboratory, Toyo University, 5-28-20 Hakusan, Bunkyo-ku, Tokyo, 112-8606, Japan

    Takahiro Suzuki

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  1. Simona Funar-Timofei
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  2. Smaranda Iliescu
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  3. Takahiro Suzuki
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Correspondence to Simona Funar-Timofei.

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Funar-Timofei, S., Iliescu, S. & Suzuki, T. Correlations of limiting oxygen index with structural polyphosphoester features by QSPR approaches. Struct Chem 25, 1847–1863 (2014). https://doi.org/10.1007/s11224-014-0474-7

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