Side-chain phenol-functionalized poly(ether sulfone) and its contribution to high-performance and flexible epoxy thermosets

Lin, Ching Hsuan; Chen, Jui Chun; Huang, Chu Ming; Jehng, Jih‐Mirn; Chang, Hao-Chen; Juang, Tzong Yuan; Su, Wen Chiung

doi:10.1016/j.polymer.2013.10.054

Cited by 22 publications

(13 citation statements)

References 30 publications

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“…Poly(arylene ether ketone)s (PAEKs) are a class of engineering thermoplastics that possess good mechanical properties, excellent thermo‐oxidative stability and chemical resistance, giving them a wide variety of applications in automobile, aerospace and electronic fields . The introduction of functional groups into the PAEK chains provides a feasible method to tailor the chemical and physical properties to expand their applications in specific fields …”

Section: Introductionmentioning

confidence: 99%

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Soluble and crosslinkable poly(phthalazinone ether ketone)s with pendent terminal ethynyl groups: synthesis, characterization and click modification

Wang

Zong

et al. 2015

Polymer International

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New poly(phthalazinone ether ketone)s (PPEKs) with pendent terminal ethynyl groups were synthesized by the aromatic nucleophilic substitution (S N Ar) polycondensation reaction of a new bisphenol monomer, 2-(3-ethynylphenyl)hydroquinone, with 4-(4 ′ -hydroxyphenyl)phthalazin-1(2H)-one and 4,4 ′ -bis(4-fluorophenyl) ketone, followed by click modification reaction with 1-azidopyrene. Fourier transform infrared and NMR spectral data of the model compound indicated that the terminal ethynyl groups were stable in S N Ar reaction conditions, thus allowing the synthesis of the desired polymers. The PPEKs obtained with glass transition temperature (T g ) in the range 152-245 ∘ C were amorphous, characterized by wide-angle X-ray diffraction, and dissolved in organic solvent to cast into transparent and flexible films. Differential scanning calorimetry results indicated that the curing reaction of the terminal ethynyl groups of the copolymers took place upon heating to 250 ∘ C. The T g of cured PPEKs was increased to about 260 ∘ C. They also exhibited excellent thermal stability with 5% weight loss temperatures ranging from 448 to 527 ∘ C in various atmospheres. The PPEKs with pendent terminal ethynyl groups were subsequently functionalized with pyrene through click reaction. A dilute chloroform solution displayed a red-shifted emission profile.

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Section: Introductionmentioning

confidence: 99%

“…Up to now, a wide range of functional groups, including sulfonic acid, carboxyl, chloromethyl, amino, hydroxyl, iodo, indole, cyano and so on, have been introduced into PAEK chains. Oroujzadeh et al reported that pendent sulfonic acid groups in PAEKs as proton charge carriers supplied appropriate proton conductivity for fuel cells .…”

Section: Introductionmentioning

confidence: 99%

Soluble and crosslinkable poly(phthalazinone ether ketone)s with pendent terminal ethynyl groups: synthesis, characterization and click modification

Wang

Zong

et al. 2015

Polymer International

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“…We have synthesized P2 , an amino‐functionalized phosphinated PES. Although this study is an extension of a previous examination, we have observed some special characteristics for P2 . First, the synthesis of this amino‐functionalized poly(ether sulfone) is sequence‐dependent—a new finding.…”

Section: Resultsmentioning

confidence: 57%

“… Data in parentheses are those of thermosets based on a phenol‐functionalized poly(ether sulfone) and an epoxy, as reported in Ref. .…”

Section: Methodsmentioning

confidence: 99%

“…Recently, we reported a phenol‐functionalized poly(aryl ether) and a poly(aryl sulfone) and their application in the preparation of high‐performance epoxy thermosetting films. Continuing our quest for high‐performance thermosets, in this study we examined two strategies for the preparation of the phosphinated PES P2 presenting an amino group in each repeating unit.…”

Section: Introductionmentioning

confidence: 99%

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High‐performance thermosetting films based on an amino‐functionalized poly(ether sulfone)

Lin

Chen

Huang

et al. 2014

J of Applied Polymer Sci

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We have developed a sequence‐dependent synthesis of the amino‐functionalized poly(ether sulfone) P2. The amino groups of P2 act as reactive sites toward epoxy resins. After curing P2 with diglycidyl ether of bisphenol A (DGEBA) and cresol novolac epoxy (CNE), we obtained the flexible, light‐yellow, transparent, epoxy thermosetting films P2/DGEBA, and P2/CNE, respectively, having glass transition temperatures (Tg) of 258 and 274°C, respectively. In addition, we also prepared a flexible film after condensation of the amino groups of P2 with the anhydride groups of 4,4′‐oxydiphthalic anhydride (ODPA); after imidization at 300°C for 1 h, the resulting P2/ODPA thermosetting film possessed a value of Tg of 340°C. These three thermosetting films also exhibited flame retardancy with a UL‐94 VTM‐0 grade. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 40980.

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A phosphorus/silicon‐containing flame retardant based on eugenol for improving flame retardancy and smoke suppression of epoxy resin

Quan

Lin

et al. 2023

J of Applied Polymer Sci

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Epoxy resin (EP) has excellent comprehensive properties, but its inherent flammability limits its further application in high‐end industries. The present study focuses on the preparation of an efficient phosphorus/silicon‐containing flame retardant for improving the flame retardancy and smoke suppression of EP. The intermediate product ED was first obtained by the addition reaction of 9,10‐dihydro‐9‐oxa‐10‐phosphaphenanthrene‐10‐oxide (DOPO) with eugenol, and then the target flame retardant DPSi‐ED was synthesized by the Williamson etherification reaction between ED and dichlorodiphenylsilane. The flame retardant was further incorporated into EP/4,4′‐diaminodiphenylmethane (DDM) system to prepare the modified epoxy thermosets. The flame‐retardant performance and mechanism were investigated by limiting oxygen index (LOI) test, vertical combustion test, cone calorimetry, thermogravimetric analysis‐infrared spectroscopy (TG‐IR), and so forth. At the same phosphorus content (0.5 wt%), EP/DPSi‐ED thermosets exhibited superior flame‐retardant properties to EP/ED thermosets. Moreover, EP/DPSi‐ED7 achieved a LOI of 35.3% and V‐0 rating in UL‐94 testing, and compared to EP/ED7, its peak heat release rate (pHRR) and total smoke production (TSP) were reduced by 31.5% and 10.9%, respectively. The phosphorus and silicon elements synergistically contributed to the formation of a stable char layer, which acted as a physical barrier to effectively enhance the flame‐retardant properties of the thermosets. Meanwhile, the incorporation of DPSi‐ED containing flexible SiO bonds and rigid DOPO groups to some extent also improved the mechanical properties of the cured EP. Hence, this study provides an effective strategy for the preparation of bio‐based phosphorus/silica‐containing high‐efficiency and smoke‐suppressing flame retardants.

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Side-chain phenol-functionalized poly(ether sulfone) and its contribution to high-performance and flexible epoxy thermosets

Cited by 22 publications

References 30 publications

Soluble and crosslinkable poly(phthalazinone ether ketone)s with pendent terminal ethynyl groups: synthesis, characterization and click modification

Soluble and crosslinkable poly(phthalazinone ether ketone)s with pendent terminal ethynyl groups: synthesis, characterization and click modification

High‐performance thermosetting films based on an amino‐functionalized poly(ether sulfone)

A phosphorus/silicon‐containing flame retardant based on eugenol for improving flame retardancy and smoke suppression of epoxy resin

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