Synthesis and effect of hyperbranched (3-hydroxyphenyl) phosphate as a curing agent on the thermal and combustion behaviours of novolac epoxy resin

Deng, Jing; Shi, Wenfang

doi:10.1016/j.eurpolymj.2003.12.015

Cited by 35 publications

(16 citation statements)

References 23 publications

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“…However, HTTE/DGEBA blends show two more stages and still have char yields at over 8008C, which suggests that the HTTE/DGEBA blends have a higher thermal stability. 39 From Figs 9b and 10b DTG curves, it is interesting to observe that all the HTTE/DEGBA blend samples show two closely peaks. These indicate that all the HTTE/DGEBA blends show similar thermal degradation behavior.…”

Section: Glass Transition Behaviormentioning

confidence: 90%

Morphology, toughness mechanism, and thermal properties of hyperbranched epoxy modified diglycidyl ether of bisphenol A (DGEBA) interpenetrating polymer networks

Shi

Yuan

et al. 2008

Polymers for Advanced Techs

100

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New hyperbranched poly(trimellitic anhydride-triethylene glycol) ester epoxy (HTTE) is synthesized and used to toughen diglycidyl ether of bisphenol A (DGEBA) 4,4(-diaminodiphenylmethane (DDM) resin system. The effects of content and generation number of HTTE on the performance of the cured systems are studied in detail. The impact strength is improved 2--7 times for HTTE/ DGEBA blends compared with that of the unmodified system. Scanning electron microscopy (SEM) of fracture surface shows cavitations at center and fibrous yielding phenomenon at edge which indicated that the particle cavitations, shear yield deformation, and in situ toughness mechanism are the main toughening mechanisms. The dynamic mechanical thermal analyzer (DMA) analyses suggest that phase separation occurred as interpenetrating polymer networks (IPNs) for the HTTE/DGEBA amine systems. The IPN maintains transparency and shows higher modulus than the neat epoxy. The glass transition temperature (T g ) decreases to some extent compared with the neat epoxy. The T g increases with increase in the generation number from first to third of HTTE and the concentrations of hard segment. The HTTE leads to a small decrease in thermal stability with the increasing content from TGA analysis. The thermal stability increases with increase in the generation number from first to third. Moreover, HTTE promotes char formation in the HTTE/DGEBA blends. The increase in thermal properties from first to third generation number is attributed to the increase in the molar mass and intramolecular hydrogen bridges, the increasing interaction of the HTTE/ DGEBA IPNs, and the increasing crosslinking density due to the availability of a greater number of end hydroxyl and end epoxide functions.

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Section: Glass Transition Behaviormentioning

confidence: 90%

Morphology, toughness mechanism, and thermal properties of hyperbranched epoxy modified diglycidyl ether of bisphenol A (DGEBA) interpenetrating polymer networks

Shi

Yuan

et al. 2008

Polymers for Advanced Techs

100

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“…As previously reported, the LOI value of EP thermosets cured with the synthesized hyperbranched (3-hydroxyphenyl) phosphate was 30.0%, and the samples failed to pass UL-94 rating in vertical burning tests. [35] The LOI value of the epoxy resins cured with bis (4-aminophenoxy) phenylphosphine oxide was 33% / reaching 4.2%, and the thermosets had no rating in the UL-94 vertical burning tests. [36] Comparing with the reported results, the synthesized DPDCEPO curing agent possesses efficient flame retardancy of epoxy resins.…”

Section: Flame Retardancymentioning

confidence: 99%

Synthesis of a novel phosphorus-containing curing agent and its effects on the flame retardancy, thermal degradation and moisture resistance of epoxy resins

Zhang

2015

Polym. Adv. Technol.

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A novel phosphorus-containing compound diphenyl-(1, 2-dicarboxylethyl)-phosphine oxide defined as DPDCEPO was synthesized and used as a flame retardant curing agent for epoxy resins (EP). The chemical structure of the prepared DPDCEPO was well characterized by Fourier transform infrared spectroscopy, and 1 H, 13 C and 31 P nuclear magnetic resonance. The DPDCEPO was mixed with curing agent of phthalic anhydride (PA) with various weight ratios into epoxy resins to prepare flame retardant EP thermosets. The flame retardant properties, combustion behavior and thermal analysis of the EP thermosets were respectively investigated by limiting oxygen index (LOI), vertical burning tests (UL-94), cone calorimeter measurement, dynamic mechanical thermal analysis and thermogravimetric analysis (TGA) tests. The surface morphologies and chemical compositions of the char residues for EP thermosets were respectively investigated by scanning electron microscopy and X-ray photoelectron spectroscopy (XPS). The water resistant properties of the cured EP were evaluated by putting the samples into distilled water at 70°C for 168 hr. The results revealed that the EP/20 wt% DPDCEPO/80 wt% PA thermosets successfully passed UL-94 V-0 flammability rating and the LOI value was as high as 33.2%. The cone test results revealed that the incorporation of DPDCEPO effectively reduced the combustion parameters of the epoxy resin thermosets, such as heat release rate and total heat release. The dynamic mechanical thermal analysis test demonstrated that the glass transition temperature (Tg) decreased with the increase of DPDCEPO content. The TGA results indicated that the incorporation of DPDCEPO promoted the decomposition of epoxy resin matrix ahead of time and led to a higher char yield and thermal stability at high temperatures. The surface morphological structures and analysis of the XPS of the char residues of EP thermosets revealed that the introduction of DPDCEPO benefited the formation of a sufficient, compact and homogeneous char layer with rich flame retardant elements on the epoxy resin material surface during combustion. The mechanical properties and water resistance of the cured epoxy resins were also measured. After water resistance tests, the EP/20 wt% DPDCEPO/80 wt% PA thermosets retained excellent flame retardancy, and the moisture adsorption of the EP thermosets decreased with the increase of DPDCEPO content in EP thermosets because of the existence of the P-C bonds and the rigid aromatic hydrophobic structure in DPDCEPO.

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“…Jeng et al [7] used phenyl phosphonic dichloride to synthesize phosphorus-containing amines as a series of curing agents which provide epoxy polymers with high phosphorus content; Deng and Shi [8] synthesized hyperbranched (3-hydroxyphenyl) phosphate (HHPP) with high functionality as a curing agent of epoxy resins, and the LOI value was much improved; Wang and Lin [9] synthesized 2-(6-oxido-6H-dibenz(c,e)(1,2) oxaphosphorin-6-yl)-1,4-dihydroxy phenylene with 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide (DOPO), which also revealed excellent flame retardancy and mechanical properties; Shieh and Wang [10] synthesized bis(3-hydroxyphenyl) phenyl phosphate(BHPP), which was used as a curing agent for diglycidyl ether of bisphenol-A (BA-EP). The resulting phosphorous-containing epoxy resin exhibited better flame retardancy and higher thermal stability than the regular bromine containing flame retardant epoxy resin.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of a phosphorus-containing flame retardant epoxy resin based on bis-phenoxy (3-hydroxy) phenyl phosphine oxide

Ren

Sun

Binjie

et al. 2007

Polymer Degradation and Stability

149

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Synthesis and effect of hyperbranched (3-hydroxyphenyl) phosphate as a curing agent on the thermal and combustion behaviours of novolac epoxy resin

Cited by 35 publications

References 23 publications

Morphology, toughness mechanism, and thermal properties of hyperbranched epoxy modified diglycidyl ether of bisphenol A (DGEBA) interpenetrating polymer networks

Morphology, toughness mechanism, and thermal properties of hyperbranched epoxy modified diglycidyl ether of bisphenol A (DGEBA) interpenetrating polymer networks

Synthesis of a novel phosphorus-containing curing agent and its effects on the flame retardancy, thermal degradation and moisture resistance of epoxy resins

Synthesis and properties of a phosphorus-containing flame retardant epoxy resin based on bis-phenoxy (3-hydroxy) phenyl phosphine oxide

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