Synthesis of three novel phosphorus-containing flame retardants and their application in epoxy resins

Sun, Dechao; Yao, Youwei

doi:10.1016/j.polymdegradstab.2011.08.004

Cited by 146 publications

(102 citation statements)

References 29 publications

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“…Yao and coworkers [9][10][11] synthesized a range of DPIs, which presented highly flame-retardant effect in cured epoxy resin with 1.0 wt % phosphorus content. Xiong et al synthesized a kind of DPI with triazine group, which imparted improved flame retardancy to epoxy resin.…”

Section: Introductionmentioning

confidence: 99%

Flame‐retardant properties and mechanisms of epoxy thermosets modified with two phosphorus‐containing phenolic amines

Wang

et al. 2016

J of Applied Polymer Sci

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Two phosphorus-containing phenolic amines, a 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO)-based derivative (DAP) by covalently bonding DOPO and imine (SB) obtained from the condensation of p-phenylenediamine with salicylaldehyde, and its analog (AP) via the addition reaction between diethyl phosphite and SB, were used to prepare flame-retardant epoxy resins. The burning behaviors and dynamic mechanical properties of epoxy thermosets were studied by limited oxygen index (LOI) measurement, UL-94 test, and dynamic mechanical analysis. The flame-retardant mechanisms of modified thermosets were investigated by thermogravimetric analysis, Py-GC/MS, Fourier transform infrared, SEM, elemental analysis, and laser Raman spectroscopy. The results revealed that epoxy thermoset modified with DAP displayed the blowing-out effect during UL-94 test. With the incorporation of 10 wt % DAP, the modified thermoset showed an LOI value of 36.1% and V-0 rating in UL-94 test. The flame-retardant mechanism was ascribed to the quenching and diluting effect in the gas phase and the formation of phosphorus-rich char layers in the condensed phase. However, the thermoset modified with 10 wt % AP only showed an LOI value of 25.7% and no rating in UL-94 test, which was possibly ascribed to the mismatching of charring process with gas emission process during combustion. V C 2016Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016, 133, 43953.

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Section: Introductionmentioning

confidence: 99%

Flame‐retardant properties and mechanisms of epoxy thermosets modified with two phosphorus‐containing phenolic amines

Wang

et al. 2016

J of Applied Polymer Sci

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“…[24][25][26] This lower bonding strength stimulates the degradation of the phosphate to phosphoric acids, which can form stable phosphorus-carbon structures, enhancing the charring of the polymer in the condensed phase and therefore increasing the residual mass. 3,24,26,27 Also, the length of the alkyl chain in the backbone of the PPE was found to have a more significant effect on the thermal stability than the nature of the substituent in the side chain (Et or Ph). Thus, although C6-Ph shows a less pronounced decomposition than C6-Et between 250-350°C, probably because of a charring effect of the aromatic side group, the degradation profile for both polymers is very similar at temperatures above 400°C.…”

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confidence: 99%

Triazolinedione-“clicked” poly(phosphoester)s: systematic adjustment of thermal properties

et al. 2017

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The thermal properties of halogen-free flame retardant poly(phosphoester)s from acyclic diene metathesis polycondensation have been optimized by a systematic post-modification using 1,2,4-triazoline-3,5-dione derivatives. The straightforward modification not only increased their glass transition temperatures significantly but also improved the thermal stability with respect to their char yields.Poly( phosphoester)s (PPEs) can be prepared via both ringopening polymerization and polycondensation.1,2 We recently applied ADMET polycondensation to prepare a variety of PPEs. [3][4][5][6] Currently, PPEs are studied in biomedical applications for their biocompatibility, 7 biodegradability and adjus- show higher resistance to leaching and migration, compared to low molecular weight additives. 9 Indeed, phosphorus is an efficient char promoter forming an accumulated protective layer on the materials surface, which limits the release of fuel to the flame. 10,11 Additionally, PPEs typically show low toxicity or almost smoke-free burning. 12,13 Recently, the combination of phosphorus-containing flame retardants with nitrogen compounds has attracted much attention. The combination of both elements physically and chemically can dramatically improve the action of the phosphorus species in the condensed phase upon combustion. 14,15 Nitrogen compounds are believed to act by the release of inert gases or by the promotion of char formation as a result of a condensation reaction.Besides phosphorus and nitrogen, the introduction of aromatic structures is also often mentioned to promote the charring. 16As a systematic study on the thermal properties and char yield, with structural variation of the main-and side chains of PPEs, is missing in the current literature, the main goal of this research was the preparation of modified PPEs via ADMET polycondensation, as a result of the variation of both the backbone and side chains. Furthermore, we used the efficient, recently revisited "click chemistry" of 1,2,4-triazoline-3,5-diones (TAD) 17,18 to modify the double bonds along the PPE backbone to further adjust the material properties. This TADene chemistry can not only be applied as a reliable and convenient post-modification reaction of unsaturated polymers but will also introduce additional nitrogen atoms into the PPEs, which is expected to have a positive influence on their flame retardant performance. TADs are one of the most reactive (di)enophiles and show quantitative conversions at room temperature with isolated alkenes or conjugated dienes, respectively in an Alder-ene or Diels-Alder reaction. TAD has recently been applied in a wide range of applications, such as self-healing, 19 surface chemistry, 20-22 and post-modification of unsaturated ADMET polymers. 23This is the first report on the post-modification of PPEs via their internal double bonds for tuning their thermal properties. Supposing that TAD-modification can increase the glass transition temperature (T g ), this would undoubtedly broaden the range of applications for PPEs...

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“…As shown in Figure 4, the initial degradation temperature of the EP composites decrease compare with pure EP, The depressed initial degradation temperature values may be attributed to the fact that the O=P−O bond is less stable than the C−C bond [4,5]. The char yield of the EP composites at high temperatures (beyond 430°C) are higher than that for EP , these results reveal that the PDDP and APP could promote enhance the thermal stability of EP at higher temperatures.…”

Section: Cone Calorimetry Testmentioning

confidence: 95%

“…Epoxy resin (EP) have the excellent characteristics of toughness, chemical resistance, and superior electrical properties, it is widely used in coatings, electronic/electrical appliances, and adhesives [1][2][3][4][5]. However, the application value of EP is restricted by its flammability.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Polyphosphonate Flame Retardants for Epoxy Resins

Li¹,

Wang²,

Liu³

et al. 2017

Proceedings of the 2017 6th International Conference on Measurement, Instrumentation and Automation (ICMIA 2017)

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Abstract.A novel halogen-free flame retardant of polyphosphonate (PDDP), has been synthesized by the melt polymerization. The structure of PDDP has been characterized by fourier transform infrared spectroscopy and nuclear magnetic resonance spectra. Results of vertical burning (UL-94), limiting oxygen index (LOI), and the cone calorimeter test rereveal that the PDDP could effectively improve the flame-retardant performance of EP, and PDDP also have a synergistic effect with APP. With the 12wt. % PDDP loading, the EP composites reached UL-94 V-0 rating with a LOI value of 35.0%, the peak of heat release rate and total heat release value decreased by 54.8 % and 26.8%, respectively. The comprehensive test results shows that the improvement of flame retardancy of the EP composites is attributed to the synergistic action of the condensed and gas phases.

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Synthesis of three novel phosphorus-containing flame retardants and their application in epoxy resins

Cited by 146 publications

References 29 publications

Flame‐retardant properties and mechanisms of epoxy thermosets modified with two phosphorus‐containing phenolic amines

Flame‐retardant properties and mechanisms of epoxy thermosets modified with two phosphorus‐containing phenolic amines

Triazolinedione-“clicked” poly(phosphoester)s: systematic adjustment of thermal properties

Synthesis of Novel Polyphosphonate Flame Retardants for Epoxy Resins

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