Phosphorus esters of<scp>1‐dopyl</scp>‐1,2‐(4‐hydroxyphenyl)ethene as effective flame retardants for polymeric materials

Howell, Bob A.; Lienhart, Gavan W.

doi:10.1002/fam.2919

Cited by 7 publications

(3 citation statements)

References 39 publications

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“…Far fewer, those with a low level of oxygenation at phosphorus, principally those containing the 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide moiety (DOPO phosphonate), decompose in the degrading polymer matrix to generate volatile radical species which enter the gas phase and quench important combustion branching reactions [23,24]. Compounds containing both types of phosphorus functionality may display two types of flame-retardant activity [25]. In either case, the flame retardant additive must decompose in the degrading polymer matrix to generate species responsible for the observed flame retardant action.…”

Section: Introductionmentioning

confidence: 99%

Thermal Degradation of Organophosphorus Flame Retardants

Howell

2022

Polymers

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The development of new organophosphorus flame retardants for polymeric materials is spurred by relatively low toxicity, effectiveness, and demand for replacement of more traditional materials. To function, these compounds must decompose in a degrading polymer matrix to form species which promote modification of the solid phase or generate active radical moieties that escape to the gas phase and interrupt combustion propagating reactions. An understanding of the decomposition process for these compounds may provide insight into the nature of flame retardant action which they may offer and suggest parameters for the synthesis of effective new organophosphorus flame retardants. The thermal degradation of a series of organophosphorus esters varying in the level of oxygenation at phosphorus—alkyl phosphate, aryl phosphate, phosphonate, phosphinate—has been examined. Initial degradation in all cases corresponds to elimination of a phosphorus acid. However, the facility with which this occurs is strongly dependent on the level of oxygenation at phosphorus. For alkyl phosphates elimination occurs rapidly at relatively low temperature. The same process occurs at somewhat higher temperature for aryl phosphates. Elimination of a phosphorus acid from phosphonate or phosphinate occurs more slowly and at much higher temperature. Further, the acids formed from elimination rapidly degrade further to evolve volatile species.

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Section: Introductionmentioning

confidence: 99%

Thermal Degradation of Organophosphorus Flame Retardants

Howell

2022

Polymers

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“…Flame retardant treatment of epoxy resin is required to reduce flammability; traditionally, organohalogen flame retardants have been used for this purpose. However, these materials decompose in the polymer undergoing thermal degradation to generate volatile, very toxic dioxins [ 3 , 4 ]. Further, when items containing these flame retardants are discarded in a landfill, they are leached into the environment in which they are stable, persist, bioaccumulate, and enter the human food chain.…”

Section: Introductionmentioning

confidence: 99%

Fabrication of Diaminodiphenylmethane Modified Ammonium Polyphosphate to Remarkably Reduce the Fire Hazard of Epoxy Resins

et al. 2021

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A novel diaminodiphenylmethane (DDM) modified ammonium polyphosphate (APP) flame retardant, DDP, was successfully synthesized via ion-exchange reaction. DDP was introduced into epoxy resins (EPs) to reduce flammability. A comparable level of DDP exerts better flame-retardant and smoke suppression efficiencies in EP than APP. An EP blend containing 15 wt% DDP displays a limiting oxygen index (LOI) value of 37.1% and a UL 94 V-0 rating, and further exhibits a 32.3% reduction in total heat release and a 48.0% reduction in total smoke production compared with pure EP. The presence of DDP greatly facilitates char formation during combustion, and the char mass from thermal decomposition of an EP blend is 37.8% smaller than that of an EP blend containing 15 wt% DDP at 800 °C. The incorporation of DDP into EP blends has a smaller impact on the glass transition temperature and tensile strength than those of a comparable level of APP. This reflects the better compatibility of DDP with the EP matrix compared with that for APP.

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“…Generally speaking, these compounds are relatively stable and difficult to degrade in nature, they may even enter the human body through the food chain, so as to endanger human health. [ 8,9 ] The eco‐friendly halogen‐free flame retardants thereby have gradually become a hotspot. Flame retardants are classified as additive and reactive flame retardants according to their flame‐retardant methods.…”

Section: Introductionmentioning

confidence: 99%

A DOPO Derivative Constructed by Sulfaguanidine and Thiophene toward Enhancing Fire Safety, Smoke Suppression, and Mechanical Properties of Epoxy Resin

Duan

Zou

Cao

et al. 2021

Macro Materials & Eng

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In order to eliminate the negative effect of traditional 9,10‐dihydro‐9‐oxa‐10‐phosphaphenanthrene‐10‐oxide (DOPO) ‐based flame retardants on heat resistance, mechanical properties, and curing process of epoxy resin (EP), a DOPO derivative (DST) constructed by sulfaguanidine and thiophene is designed and used as co‐cured agent for EP. Compared with EP, the maximum decrease of glass transition temperature (Tg) in all EP/DST samples is less than 5%, indicating EP modified by DST maintains good heat resistance. Encouragingly, DST shows satisfactory flame‐retardant efficiency and excellent smoke suppressing effects. EP containing barely 5 wt% of DST (P content: 0.37 wt%) achieves a UL‐94 V‐0 rating and 32.8% limited oxygen index (LOI) value. Its peak heat release rate (PHRR), total heat release (THR), and total smoke production (TSP) are also decreased by 31.2%, 18.8%, and 30.2% . Further, DST significantly improves mechanical properties of the EP/DDM/DST system. The tensile strength and modulus increase by 37.2% and 14.6%, respectively, as DST content is 7.5 wt%. It is revealed that DST has positive quenching and diluting effects in the gas phase, as well as promoting the formation of a compact char layer in the condensed phase.

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Phosphorus esters of1‐dopyl‐1,2‐(4‐hydroxyphenyl)ethene as effective flame retardants for polymeric materials

Cited by 7 publications

References 39 publications

Thermal Degradation of Organophosphorus Flame Retardants

Thermal Degradation of Organophosphorus Flame Retardants

Fabrication of Diaminodiphenylmethane Modified Ammonium Polyphosphate to Remarkably Reduce the Fire Hazard of Epoxy Resins

A DOPO Derivative Constructed by Sulfaguanidine and Thiophene toward Enhancing Fire Safety, Smoke Suppression, and Mechanical Properties of Epoxy Resin

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