A tryptamine-based DOPO derivative as a flame retardant for epoxy resins

Ren, Jiexiang; Yang, Guichun; Deng, Xiaocong; Huang, Shengchao; Lu, Cuifen

doi:10.1016/j.polymdegradstab.2023.110595

Cited by 10 publications

(1 citation statement)

References 57 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Simultaneously, phosphorus-containing compounds serve as catalysts in the generation of a protective char layer on the material’s surface, acting as a barrier that restricts the ingress of oxygen and heat into the underlying material . Furthermore, the emitted phosphorus-containing gases not only can dilute the flammable gases produced during combustion but also disrupt the combustion process by scavenging free radicals and inhibiting reactions such as the •PO and •PO 2 radicals cover hydrogen (•H) and hydroxyl (•HO) radicals, thereby reducing the concentration of flammable gases through effective quenching and dilution. ,− In summary, the cleavage of P–C bonds during combustion and the subsequent release of phosphorus-containing species contribute to the formation of a protective char layer, ultimately enhancing the flame-retardant properties of the material. Therefore, it is imperative for us to comprehend a key thermodynamic aspect of the P–C bond, specifically, the strength of the P–C bond, which can be quantified through the determination of homolytic bond dissociation enthalpies (BDEs).…”

Section: Introductionmentioning

confidence: 99%

Theoretical Study on the P–C Bond Dissociation Enthalpy in 9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide Flame Retardants

Jiao,

Zheng,

Cui

et al. 2024

J. Phys. Chem. A

View full text Add to dashboard Cite

The 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) flame retardants (DOPO-FRs) have attracted more and more attention in the flame-retardant industry due to their high efficiency, environmental protection, and good molecular design. During the flame-retardant process, the breakage of P−C bonds is very important to the flame-retardant effect. Through the comparison of different density functional theories (DFTs) on P− C BDEs, it was found that MN12-L has the highest calculation accuracy, and the root-mean-square error is the smallest with 1.85 kcal/mol. Therefore, MN12-L was selected to investigate P−C BDEs of different DOPO-FRs including thiophen-amine, benzo-[d]thiazol-amine, triazol-amine, and aniline DOPO-FRs. By comparing the theoretical calculation of BDE with the experimental parameters of high limiting oxygen index (LOI) and vertical combustion test (UL-94 test), it was found that the P−C BDEs have a certain correlation with the flame-retardant effect. Finally, based on P−C BDEs, substituent effects, and effective flame-retardant fragments, a series of new DOPO-FRs were designed. The results showed that when only one DOPO fragment was contained, the effective fragments of flame retardants were ranked as furan > thiophene > triazole > imidazole. When bis-DOPO fragment was contained, the flame-retardant effect of diamino-triazole fragments was better than that of benzyldimethylamine fragments. In addition, when the substituents on the effective fragment have two EDGs, the flame-retardant effect is superimposed, which makes the flame-retardant performance more excellent.

show abstract

Section: Introductionmentioning

confidence: 99%

Theoretical Study on the P–C Bond Dissociation Enthalpy in 9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide Flame Retardants

Jiao,

Zheng,

Cui

et al. 2024

J. Phys. Chem. A

View full text Add to dashboard Cite

show abstract

Cyano group‐containing DOPO derivative for improving the flame retardancy, smoke suppression, and mechanical properties of epoxy resins

Zhang,

Ma,

Gao

et al. 2024

J of Applied Polymer Sci

View full text Add to dashboard Cite

In order to obtain an efficient flame retardant and smoke suppressor without sacrificing mechanical properties of epoxy resin (EP). A cyano group‐containing 9,10‐dihydro‐9‐oxa‐10‐phosphaphenanthrene‐10‐oxide (DOPO) derivative (CP‐DOPO) was proposed and synthesized through one‐step Atherton–Todd reaction between DOPO and 4‐cyanophenol. The comprehensive performance analysis of CP‐DOPO‐based EP composite was conducted by measuring the flame retardancy, smoke suppression, and mechanical properties. The flame‐retardant test findings shows that the EP/4CP‐DOPO sample achieves UL‐94 V‐0 rating with 4 wt% low addition of CP‐DOPO. Moreover, EP/6CP‐DOPO sample presents a LOI of 36.5%, a 28.1% reduction in the peak heat release rate, and a 42.1% substantial decrease in total smoke production, demonstrating its desirable flame retardancy and smoke suppression properties. Significantly, different from the traditionally additive flame retardants, the mechanical properties of EP matrix will not be affected by the incorporation of CP‐DOPO but a 17.7% increasement of flexural properties compared to EP. This research not only provides an ingenious strategy for designing and preparing high‐effective flame retardant but also enhances the comprehensive performance of EP resins in practical applications.

show abstract

A Cu‐MOF‐decorated ammonium polyphosphate for epoxy resins with reduced smoke release and enhanced char layer

Chai,

Hou,

Zhang

et al. 2024

J of Applied Polymer Sci

View full text Add to dashboard Cite

Inspired by the significant catalytic charring effect of metal–organic frameworks (MOFs), Cu‐MOF decorated ammonium polyphosphate (APP@Cu‐MOF) was prepared by coupling agents to improve the fire safety of epoxy resin (EP). After adding 9 wt% APP@Cu‐MOF, the fire performance of EP is significantly improved with limiting oxide index (LOI) value of 29.4 and UL‐94 V‐0 rating. The peak heat release rate (PHRR), total smoke production (TSP), CO production, and CO2 production of EP composite samples decreased by 34.6%, 54.7%, 24.6% and 30.0%, respectively. It is proposed that the synergistic effect among Cu‐MOF and APP promoted the char formation of EP. The dense carbon layers formed a barrier that prevented the transfer of heat and inhibited the release of toxic gases, thus acting as a flame retardant. This work provides a new strategy to develop a high‐efficient MOF‐decorated flame retardant with smoke inhibition, toxicity reduction, and catalytic carbonization effect.

show abstract

A tryptamine-based DOPO derivative as a flame retardant for epoxy resins

Cited by 10 publications

References 57 publications

Theoretical Study on the P–C Bond Dissociation Enthalpy in 9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide Flame Retardants

Theoretical Study on the P–C Bond Dissociation Enthalpy in 9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide Flame Retardants

Cyano group‐containing DOPO derivative for improving the flame retardancy, smoke suppression, and mechanical properties of epoxy resins

A Cu‐MOF‐decorated ammonium polyphosphate for epoxy resins with reduced smoke release and enhanced char layer

Contact Info

Product

Resources

About