Synthesis and Characterization of Aluminum 2-Carboxyethyl-Phenyl-Phosphinate and Its Flame-Retardant Application in Polyester

A flame retardant aluminum 2-carboxyethyl-phenyl-phosphinate (CPA-Al) was synthesized through the salification reaction. The molecular structure of CPA-Al and thermal stability were characterized by solid nuclear magnetic resonance, Fourier transform infrared spectroscopy, and thermogravimetric analysis. Subsequently, CPA-Al mixed in polyurethane was coated on polyester textile to obtain flame-retardant samples. The addition of 14.7 wt.% CPA-Al in textile sample can bring a limited oxygen index (LOI) value of 24.5%, 0 s after flame time, and the vertical burning B1 rating. Meanwhile, the incorporated CPA-Al reduced the peak heat release rate, total heat release, average effective heat of combustion, and increased the charring capacity of polyester textiles in contrast to the samples without CPA-Al. CPA-Al exerted not only its flame inhibition effect in gas phase, but also the charring and barrier effect in the condensed phase. Besides, with an increasing CPA-Al ratio in polyester textile, the contact angle gradually decreased from 123.6° to 75.6°, indicating that the surficial property of coating from hydrophobic to hydrophilic, thereby increasing the moisture permeability of polyester textile.

Insight into the Synthesis and Characterization of Organophosphorus-Based Bridged Triazine Compounds

In this article, we report the synthesis of 2,4,6-substituted s-triazine-based organophosphorus compounds via a two-step process, which enables their production in high yields, and with a high purity as solids. In the first step, a Michaelis–Arbuzov rearrangement of cyanuric chloride with triethyl phosphite afforded 2,4,6-trisdiethoxyphosphinyl-1,3,5-triazine (HEPT). Subsequently, the nucleophilic substitution reaction on the triazine carbon was achieved, owing to the electron-withdrawing ability of the phosphonate groups. This characteristic of HEPT facilitated its derivatization with bi-functional amines, producing novel P–C containing bridged triazine organophosphorus compounds. The molecular structures of all of the compounds were confirmed by NMR spectroscopy, CHN elemental analysis, and single crystal X-ray analysis. In the thermogravimetric analysis in an N2 environment, >33% char formation was observed for the bridged compounds. The chemical composition analysis of the char obtained under the oxidative thermal decomposition of the bridged compounds confirmed the presence of phosphorus- and nitrogen-enriched species, which indicate their function in the condensed phase. Comparatively, the detection of HPO and H–C≡P in the gas phase during the pyrolysis of the bridged compounds can act as a source for PO•, which is known for its gas phase flame inhibition reactions. The synergy of significant char formation and the generation of intermediates leading to PO• during pyrolysis makes these molecules promising flame-retardant additives.

Flame Inhibition and Charring Effect of Aromatic Polyimide and Aluminum Diethylphosphinate in Polyamide 6

An aromatic macromolecular polyimide (API) was synthesized and characterized, and used as a synergistic charring flame retardant in glass fiber reinforced polyamide 6 (GF/PA6). API and aluminum diethylphosphinate (ADP) exhibited better flame inhibition behavior and synergistic charring flame retardant behavior compared with ADP alone. The 5%API/7%ADP/GF/PA6 sample achieved the lower peak value of the heat release rate (pk-HRR) at 497 kW/m2 and produced higher residue yields of 36.1 wt.%, verifying that API and ADP have an outstanding synergistic effect on the barrier effect. The API/ADP system facilitated the formation of a carbonaceous, phosphorus and aluminum-containing compact char layer with increased barrier effect. FTIR spectra of the residue and real-time TGA-FTIR analysis on the evolved gases from PA6 composites revealed that API interacted with ADP/PA6 and locked in more P–O–C and P–O–Ar content, which is the main mechanism for improving flame inhibition and charring ability. In addition, the API/ADP system improved the mechanical properties and corrosion resistance of GF/PA6 composites compared to ADP alone.