Thermal degradation of phosphorus esters derived from isosorbide and 10-undecenoic acid

Abstract

Phosphorus compounds derived from renewable biomaterials are of increasing interest as polymer additives. These compounds may have both a plasticizing and flameretarding effect on a polymer matrix into which they are incorporated. The thermal degradation of a series of phosphorus esters derived from a diol generated by the esterification of isosorbide (from starch) with 10-undecenoic acid (from castor oil) followed by thiol-ene reaction with 2-hydroxyethanethiol has been examined using thermogravimetry and infrared spectroscopy. All the esters undergo degradation over the temperature range of 250-310°C to generate a substantial residual char. Infrared analysis of samples undergoing degradation suggests that a prominent reaction is elimination of a phosphorus acid.

From a bio-based phosphorus-containing epoxy monomer to fully bio-based flame-retardant thermosets

“…The most actual trends of green solutions for ame retardancy have been gathered in a recent book. 21 In a recent paper, 22 our team reported the synthesis of several bio-based phosphoruscontaining additive ame retardants by graing phosphate functions onto hydroxyl groups of phloroglucinol, a bio-based phenolic molecule found in the bark of fruit trees. 10 Once again, various fractions of the biomass have been considered in the literature to promote biobased FR.…”

Incorporation of Comonomer exo-5-(Diphenylphosphato)Isosorbide-2-endo-Acrylate to Generate Flame Retardant Poly(Styrene)

“…This is largely driven by concern about the release of toxic agents to the environment and the likely negative impact of these materials on human health. Flame retardants, in particular have been a focus of much of this development [40][41][42][43][44][45][46][47][48][49]. Precursors for biobased flame retardants may come from a variety of sources including plant oils [49], seed grain constituents [50,51], and by-products of food manufacture [47,49].…”

“…In general ester synthesis and polymerization were carried out using the previously described methods [44,45]. Characterization was accomplished using chromatographic, thermal, and spectroscopic methods as previously described [44,45,53,54]. Thermal transitions were determined using differential scanning calorimetry (DSC) at a heating rate of 10 • C/min and a TA Instruments Q2000 instrument (TA Instruments, New Castle, DE, USA).…”

“…Isosorbide esters were prepared as previously described [44,45,53]. The polymerization is outlined in Scheme 1 and described below.…”

“…Toxicity of organophosphorus compounds is usually the consequence of a particular structure rather than a function of the compounds as a class. Organophosphorus compounds based on renewable biosources are particularly attractive [40][41][42][43][44][45][46][47][48][49]. The precursors to these compounds are usually nontoxic, benign, or biodegradable in the environment, often renewable annually, and available at costs that are independent of fluctuations in petrochemical markets.…”