Synthesis, thermal property and hydrolytic degradation of a novel star-shaped hexa[p-(carbonylglycinomethylester)phenoxy]cyclotriphosphazene

Abstract

A novel star-shaped cyclotriphosphazene substituted by glycinomethylesterphenoxy and its intermediates are synthesized from hexachlorocyclotriphosphazene (HCCP). The structures are characterized by 1 H NMR, 13 C NMR, 31 P NMR, FTIR and elemental analysis. Their thermal properties are clarified by thermogravimetric analysis (TGA), differential scanning calorimentry (DSC) and FTIR, while hydrolytic degradation behaviour is studied with UV-vis spectrophotometer and by measuring the weight loss, and the phosphorus content of residue. According to hydrolysis behaviour of hexa[p-(carbonylglycinomethylester)phenoxy]cyclotriphosphazene (HGPCP) under different conditions, it is easy to hydrolyze in hydrochloric acid (pH 1.0) than in phosphate buffer (pH 7.4) at 37℃. And the sample hydrolytic degradation still remains at the stage of side groups' break. The TGA data show that the thermal stability of the hexa[p-(aldehyde)phenoxy]cyclotriphosphazene (HAPCP), hexa[p-(carboxyl) phenoxy]cyclotriphosphazene (HCPCP) andHGPCP is so high that their char residues are 75%, 47% and 47% at 800℃, respectively, probably due to cross-linking between molecules.phosphazene, glycino methyl ester, synthesis, hydrolytic degradation, thermal properties

Synthesis and characterization of a novel epoxy resin based on cyclotriphosphazene and its thermal degradation and flammability performance

“…According to our previous work [36], hexa-(4-carboxyl-phenoxy)-cyclotriphosphazene (HCPCP) was obtained from oxidizing hexa-(4-aldehyde-phenoxy)-cyclotriphosphazene (HAPCP) by potassium permanganate. 33.3 g potassium permanganate (0.21 mol), 6.3 g sodium hydroxide (0.16 mol) and 320 mL H 2 O was added to the solution of 21 g HAPCP (0.024 mol) in 400 mL THF in a threeneck-flask equipped with a mechanical stirrer and refluxing condenser, then the reaction mixture was stirred for 30 h at refluxing temperature.…”

Self-assembly of nanoparticles from cyclotriphosphazenes grafted with hexa-[p-(carbonyl tryptophan ethyl ester) phenoxy)] group

“…The target compound of HEPCP was synthesized according to the following steps. Firstly, hexa-[p-(carboxyl) phenoxy] cyclotriphosphazene (N 3 P 3 (p-O-C 6 H 4 -COOH) 6 , HCPCP) was prepared according to the literature 24 and activated in thionyl chloride, then the acid chloride was reacted with tryptophan ethyl ester (EtTrp) for 48 h in THF under a circumfluence condition, triethylamine was used to neutralize the byproduct hydrochloride. After the reaction, most of the solvent was evaporated under vacuum and the solution was dropped into petroleum ether, the product was separated out and washed by excess deionized water.…”

“…1. The cyclotriphosphazene compound HCPCP, as a starting material, was prepared according to the literature 24 and firstly activated in thionyl chloride. The object compound appended with six p-(carbonyl tryptophan ethyl ester) phenoxycontaining groups, HEPCP, was obtained by reaction of acid chloride with primary amine of EtTrp.…”

“…12b, which could be ascribed to the decomposition of the ester bond and followed by the breaking of the acylamide bond. 24 The main decomposition appeared at 360 uC due to the decomposition of cyclotriphosphazene and phenyl structures. For the as-prepared nanoparticles, there are also two weight loss sections during the thermal degradation process, but the initial decomposition occurred at 305 uC, an increase of 50 uC, which was indicative of a new interaction force between the HEPCP molecules during the self-assembly process.…”