High‐<i>T</i><sub>g</sub> Transparent Poly(ether sulfone)s Based on Phosphinated Bisphenols

Lin, Ching Hsuan; Chang, Sheng Lung; Wei, Tsai Pei

doi:10.1002/macp.201000505

Cited by 13 publications

(6 citation statements)

References 41 publications

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“…Generally, DOPO is directly used as a flame retardant in prepolymers of EP resin, and it was covalently linked to the EP resin. 9 –18 However, there still exist some problems of the DOPO-modified EP resins: (1) relatively high dosage of DOPO, (2) decreased T g , (3) poor humidity resistance property, and (4) decreased decomposed temperature. 19 –21 In order to overcome the aforementioned problems, many studies have been carried out on designing special DOPO derivatives.…”

Section: Introductionmentioning

confidence: 99%

A novel curing agent based on diphenylphosphine oxide for flame-retardant epoxy resin

Huang

Hou

et al. 2017

High Performance Polymers

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A phosphorous/nitrogen-containing diphenylphosphine oxide (DPO) derivative (DPO-SS) was designed and synthesized via a two-step reaction of 4,4′-diaminodiphenylsulfone, 2-hydroxy-benzaldehyde, and DPO. The structure of DPO-SS was confirmed by Fourier transform infrared spectroscopy (FTIR), 1H and 31P nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS). DPO-SS was used as a flame retardant and curing agent for copolymerizing with diglycidyl ether of bisphenol-A. Thermal and flame-retardant properties of the obtained flame-retardant epoxy resin (F-EP) were investigated by thermogravimetric analysis, dynamic thermomechanical analysis, limited oxygen index (LOI) measurement, vertical burning test (UL-94), and cone calorimeter test. Results indicated that all F-EP samples exhibited excellent thermal stability and flame-retardant property. Especially for F-EP with P content of 0.7 wt% (denoted as EP/P-0.7), it achieved high LOI values (32.4%) and UL-94 V-0 rating. Compared with pure EP, all F-EP samples showed lower heat release rate, total heat release, total smoke produce, and little Tg fluctuation. In order to study the flame-retardant mechanism, the char residues were investigated by FTIR, scanning electron microscopy, and energy-dispersive spectrometer analysis. The results manifested that DPO-SS acted as flame retardant in both gas phase and condensed phase. Water absorption properties of pure EP and F-EP were also compared through immersion experiments. Results showed that EP/P-0.7 sample had apparently lower water absorptivity than pure EP.

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Section: Introductionmentioning

confidence: 99%

A novel curing agent based on diphenylphosphine oxide for flame-retardant epoxy resin

Huang

Hou

et al. 2017

High Performance Polymers

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“…The DOPO-BPA monomer was synthesized according to reported procedures (Figure ). , Briefly, DOPO (10.81 g, 0.05 mol), 4-hydroxyacetophenone (6.81 g, 0.05 mol), p-TSA (0.432 g, 0.0025 mol), and phenol (14.11 g, 0.15 mol) were added to a three-neck round-bottom flask and stirred for 10 h at 60 °C. The obtained DOPO-BPA was filtered with methanol and dried in an oven at 100 °C.…”

Section: Methodsmentioning

confidence: 99%

Improving the Durability and Performance of Sulfonated Poly(arylene ether)s by Introducing 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide Structure for Fuel Cell Application

Kang

Lee

2021

ACS Omega

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Polymer electrolyte membranes in which the hydrophilic and hydrophobic domains phase separate exhibit improved properties and stability. Such a phase separation of hydrophilic and hydrophobic domains can be achieved by polymerizing a 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide-bisphenol A (DOPO-BPA) and 1,4-bis(4-fluorobenzoyl)benzene (1,4-FBB) monomer. In this work, sulfonated polymer membranes with various degrees of sulfonation (DS) were prepared and their physicochemical and electrochemical properties were studied. In addition, the effect of molecular structure on the durability of the copolymers was investigated. The sulfonated copolymers were characterized by Fourier-transform infrared spectroscopy and proton nuclear magnetic resonance spectroscopy. Then, sulfonated membranes were prepared using these copolymers by the solvent casting method, and their morphologies were investigated by atomic force microscopy. The effect of DS on the thermal, mechanical, and oxidative stabilities, water uptake behavior, and ion-exchange capacity of the membranes was determined. The results showed that compared with the commercially available Nafion 212 polymer electrolyte membrane, the electrolyte membrane based on DOPO-BPA and 1,4-FBB exhibited a lower water uptake and excellent dimensional stability despite having a relatively high ion-exchange capacity. The low water uptake is an important characteristic that ensures the stability of the polymer electrolyte membrane in fuel cell applications.

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“…The experimental values corresponded to vinylic polymers, polyesters, polyarylates, poly(ether sulfone)s, aromatic polyamides, and aromatic polyimides, all comprising one or two DOPO‐derived substituent group within the repeat unit. Only experimental values of T g of aromatic polyimides appeared really far from the estimation (Figure ).…”

Section: Resultsmentioning

confidence: 99%

DOPO‐Based Phosphorus‐Containing Methacrylic (Co)Polymers: Glass Transition Temperature Investigation

Bier

Six

Durand

2019

Macro Materials & Eng

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flame retardant, DOPO is also attractive because PH bond can be easily modified into PN, PO, or PC bonds, leading to improved thermal stability. [5][6][7][9][10][11][12] DOPO has been successfully used as an additive in many polymers (additive strategy) such as epoxy resins, [13,14] polyurethane, [9] acrylonitrile-butadiene-styrene copolymers, [15] polyamide, [16] and poly(methyl methacrylate) (PMMA). [17] Alternatively, DOPO-based monomers have been used to prepare matrices with chemically bound flame-retardant groups (reactive strategy) by step polymerization, like epoxy resins, [18][19][20][21] polyurethane, [22] poly(ethylene terephthalate), [23] polyamide, [24] ethylenevinyl acetate copolymer, [25] and polysulfone. [26,27] Nevertheless, to the best of our knowledge, only one study has been reported about the synthesis and application of DOPO-derived acrylate monomer for the preparation of flame resistant thermoplastic matrix by free radical polymerization. [28] More precisely, the latter monomer was first derived from acryloyl chloride with DOPO covalently linked as side group, then copoly merized with methyl methacrylate (MMA).Because of the very limited number of available studies, there is a need for new flame-retardant monomers able to react with common monomers via free radical polymerization. While bringing flame-retardant properties, these monomers should also preserve mechanical properties of final polymeric materials. The first requirement regarding mechanical properties is generally that the materials exhibit a high enough glass transition temperature (T g ) as compared to the conditions of targeted application. Indeed, when flame-retardant additives are blended with thermoplastics, they often act as plasticizers and consequently lower the T g of the final material, which may be a serious drawback. Such effect has been reported for DOPO. [17] Thus, the reactive strategy appears promising for providing efficient flame-retardant properties while limiting undesirable plasticizing effect.This work aimed at exploring a reactive strategy involving the design and the use of functional monomers with DOPO pending groups for including significant amounts of phosphorus in the material while keeping high enough T g . To that goal, DOPO was used as the precursor of the flame-retardant moiety and was covalently linked to methacrylate groups by aliphatic hydrocarbon spacers with number of carbon atoms ranging between 3 and 11 (Figure 2). Chemical structure and purity of the prepared novel phosphorus-containing methacrylic monomers were verified by combining several NMR Phosphorus-Containing MethacrylatesA two-step synthetic procedure is designed for preparing new flame-retardant methacrylic monomers containing 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) as a substituent side group. DOPO and methacrylate moieties are linked by linear aliphatic hydrocarbon spacers (3 to 11 carbon atoms). Copolymerization with methyl methacrylate is carried out leading to copolymers containing between 2 and 10 wt% ...

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High‐T_g Transparent Poly(ether sulfone)s Based on Phosphinated Bisphenols

Cited by 13 publications

References 41 publications

A novel curing agent based on diphenylphosphine oxide for flame-retardant epoxy resin

A novel curing agent based on diphenylphosphine oxide for flame-retardant epoxy resin

Improving the Durability and Performance of Sulfonated Poly(arylene ether)s by Introducing 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide Structure for Fuel Cell Application

DOPO‐Based Phosphorus‐Containing Methacrylic (Co)Polymers: Glass Transition Temperature Investigation

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High‐Tg Transparent Poly(ether sulfone)s Based on Phosphinated Bisphenols

Cited by 13 publications

References 41 publications

A novel curing agent based on diphenylphosphine oxide for flame-retardant epoxy resin

A novel curing agent based on diphenylphosphine oxide for flame-retardant epoxy resin

Improving the Durability and Performance of Sulfonated Poly(arylene ether)s by Introducing 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide Structure for Fuel Cell Application

DOPO‐Based Phosphorus‐Containing Methacrylic (Co)Polymers: Glass Transition Temperature Investigation

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High‐T_g Transparent Poly(ether sulfone)s Based on Phosphinated Bisphenols