Synthesis, flame retardancy, and thermal degradation behaviors of novel organo-phosphorus compounds derived from 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO)

Kim, Woojung; Hoang, DongQuy; Vothi, Hai; Nguyen, Congtranh; Giang, Thanhkieu; An, Haiyan; Kim, Jinhwan

doi:10.1007/s13233-016-4012-x

Cited by 20 publications

(16 citation statements)

References 22 publications

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“…In addition, DOPO could catalyze the formation of polymer coke and act as a synergistic flame retardant between gas phase and solidification phase [4]. Kim W research group [5] synthesized a series of DOPO derivatives FR and applied them to acrylonitrile-butadienestyrene copolymer (ABS). The results showed that when the load of FR is 27.5-30.0 wt%, the flame-retardant performance of ABS/FR mixture can be significantly improved, which can reach V-0 rating, and smoke emission can be greatly reduced.…”

Section: Introductionmentioning

confidence: 99%

A study on preparation of modified Graphene Oxide and flame retardancy of polystyrene composite microspheres

Wang

Qing

Sun

et al. 2020

Designed Monomers and Polymers

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In this paper, the ODOPM, a kind of 9, 10-dihydro-9-oxygen-heterooxy-10-phosphoro-10-oxygen (DOPO) derivative, was obtained by hydroxylation of DOPO. Further, a phosphorus nano-flame retardant (GO-ODOPM) was obtained by addition reaction with carboxylated Graphite Oxide (GO-COOH). And then Graphene Oxide/polystyrene (GO-ODOPM/PS) composite microspheres were obtained via suspension polymerization of styrene with GO-ODOPM. The decrease of the peak heat release rate (HRR) and total heat release rate (THR) for the GO-ODOPM/PS composite microspheres was obtained when the content of the additives was only 3.0 wt% is more than 36.2% and 33.6% compared with the pure PS microspheres, respectively. Thermogravimetric (TG), dynamic rheology and carbon residue analysis were used to study the flame-retardant mechanism of GO-ODOPM in PS microspheres. The results revealed that the addition of GO-ODOPM obviously reduced the fire hazard of polystyrene (PS) microspheres. Thus, this work provided a feasible method to design efficient flame retardants for enhancing fire safety of polymers. ARTICLE HISTORY

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Section: Introductionmentioning

confidence: 99%

A study on preparation of modified Graphene Oxide and flame retardancy of polystyrene composite microspheres

Wang

Qing

Sun

et al. 2020

Designed Monomers and Polymers

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“… For many years, various flame retardants (FRs) are used to reduce the potential fire dangers associated with the EP. Traditional halogenated flame retardants (HFRs) demonstrate remarkable flame retardance efficiency. However, there are serious disadvantages such as the release of poisonous and corrosive fumes from HFRs during combustion .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a caged bicyclic phosphates derived anhydride and its performance as a flame‐retardant curing agent for epoxy resins

Liu

et al. 2019

Polymers for Advanced Techs

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A novel curing and flame‐retardant agent (PEPA‐TMAC) was successfully synthesized. The chemical structure was characterized by Fourier transform infrared spectroscopy (FTIR) and nuclear magnetic resonance (NMR). Use of PEPA‐TMAC as part of the curing agent in combination with another anhydride for a commercial epoxy resin (EP) was studied. Results of differential scanning calorimetry (DSC) indicated that PEPA‐TMAC was an effective curing agent for EP. The dynamic mechanical analysis (DMA) results showed that the glass transition temperature (Tg) and cross‐linking density (Ve) of EP composites exhibited an increase trend with the addition of PEPA‐TMAC. The limiting oxygen index (LOI) value of EP composites reached 26.9%, and the cone calorimeter results indicated that peak heat release rate (PHRR), total heat release (THR), smoke produce rate (SPR), and total smoke produce (TSP) remarkably decreased with increasing PEPA‐TMAC content. TGA data showed that the addition of PEPA‐TMAC greatly increased the amount of residual char during combustion. The morphology of the residual char was studied by SEM and showed that the addition of PEPA‐TMAC greatly increased the stability of EP composites. The thermogravimetric analysis (TGA), energy‐dispersive X‐ray spectroscopy (EDS), and FTIR results revealed the flame‐retardant mechanism that PEPA‐TMAC can promote the formation of charred layers with the phospho‐carbonaceous complexes in the condensed phase during burning of EP composites.

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“…In addition to its efficiency as 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 . DOPO has been successfully used as an additive in many polymers (additive strategy) such as epoxy resins, polyurethane, acrylonitrile‐butadiene‐styrene copolymers, polyamide, and poly(methyl methacrylate) (PMMA) . Alternatively, DOPO‐based monomers have been used to prepare matrices with chemically bound flame‐retardant groups (reactive strategy) by step polymerization, like epoxy resins, polyurethane, poly(ethylene terephthalate), polyamide, ethylene‐vinyl acetate copolymer, and polysulfone .…”

Section: Introductionmentioning

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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Synthesis, flame retardancy, and thermal degradation behaviors of novel organo-phosphorus compounds derived from 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO)

Cited by 20 publications

References 22 publications

A study on preparation of modified Graphene Oxide and flame retardancy of polystyrene composite microspheres

A study on preparation of modified Graphene Oxide and flame retardancy of polystyrene composite microspheres

Synthesis of a caged bicyclic phosphates derived anhydride and its performance as a flame‐retardant curing agent for epoxy resins

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

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