Abstract
A phosphorus containing acrylate monomer has been constructed from isosorbide, a renewable biomaterial. Treatment of isosorbide with diphenylchlorophosphate generates a mixture of phosphorus esters from which exo-5-(diphenylphosphato)isosorbide-2-endo-ol may be isolated using column chromatography. Conversion of the alcohol to the corresponding acrylate by treatment with acroyl chloride provides a reactive acryloyl monomer containing a diphenylphosphato unit. Copolymerization of this monomer, at levels to provide 1% or 2% phosphorus incorporation, with styrene generates a polymer with substantially diminished flammability compared to that for styrene homopolymer.
Highlights
In the decades since World War II, the development of polymeric materials has been a major contributor to the well-being of modern society [1,2]
Many flame retardants function by promoting the formation of protective char layer at the surface of the degrading polymer, while others release volatile components to the gas phase which scavenge combustion-propagating radicals [12]
Among these, brominated aromatics have been most commonly used. These materials are readily available, modest in cost and effective as flame retardants [14,15]. They function by releasing volatile hydrogen bromide, formed by interaction with the thermally-degrading polymer, to the gas phase where it traps radicals which propagate the combustion process [12]
Summary
In the decades since World War II, the development of polymeric materials has been a major contributor to the well-being of modern society [1,2]. Many flame retardants function by promoting the formation of protective char layer at the surface of the degrading polymer, while others release volatile components to the gas phase which scavenge combustion-propagating radicals [12]. These materials are readily available, modest in cost and effective as flame retardants [14,15] They function by releasing volatile hydrogen bromide, formed by interaction with the thermally-degrading polymer, to the gas phase where it traps radicals which propagate the combustion process [12]. The action of these compounds is enhanced by the presence of antimony oxide. Organohalogen compounds have long been widely used as flame retardants, this use is coming under increasing societal and regulatory pressure [17,18]
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