Phosphorus‐Containing Polymer Flame Retardants for Aliphatic Polyesters

Schwarzer, Madeleine; Korwitz, Andreas; Komber, Hartmut; Häußler, Liane; Dittrich, Bettina; Schartel, Bernhard; Pospiech, Doris

doi:10.1002/mame.201700512

Cited by 16 publications

(13 citation statements)

References 41 publications

(77 reference statements)

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“…ItaP, a DOPO-containing polyester which already showed good fire behavior but wasn't investigated in PLA yet, was also tested in order to compare the efficiency of the synthesized flame retardants. [30,31] Since the fire behavior depends not only on the mode of action of the flame retardants and their interaction with the polymeric matrix, but also strongly on physical phenomena like melt dripping which correlates to the viscosity of the melt, two PLAs with different melt viscosities are investigated. [37] The composition of the formulations and the results are represented in Table 3 for the PLA with low viscosity (MFR, g/10 min, 210 • C, 2.16 kg: 80) and Table 4 for the PLA with higher viscosity (MFR, g/10 min, 210 • C, 2.16 kg: 14).…”

Section: Burning Behavior Of the Flame Retardants In Plamentioning

confidence: 99%

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Synthesis of Novel Polymeric Acrylate-Based Flame Retardants Containing Two Phosphorus Groups in Different Chemical Environments and Their Influence on the Flammability of Poly (Lactic Acid)

et al. 2020

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Novel polymeric acrylate-based flame retardants (FR 1–4) containing two phosphorus groups in different chemical environments were synthesized in three steps and characterized via nuclear magnetic resonance (NMR) spectroscopy, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and mass spectrometry (MS). Polylactic acid (PLA) formulations with the synthesized compounds were investigated to evaluate the efficiency of these flame retardants and their mode of action by using TGA, UL94, and cone calorimetry. In order to compare the results a flame retardant polyester containing only one phosphorus group (ItaP) was also investigated in PLA regarding its flame inhibiting effect. Since the fire behavior depends not only on the mode of action of the flame retardants but also strongly on physical phenomena like melt dripping, the flame retardants were also incorporated into PLA with higher viscosity. In the UL94 vertical burning test setup, 10% of the novel flame retardants (FR 1–4) is sufficient to reach a V-0 rating in both PLA types, while a loading of 15% of ItaP is not enough to reach the same classification. Despite their different structure, TGA and cone calorimetry results confirmed a gas phase mechanism mainly responsible for the highly efficient flame retardancy for all compounds. Finally, cone calorimetry tests of the flame retardant PLA with two heat fluxes showed different flame inhibiting efficiencies for different fire scenarios.

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Section: Burning Behavior Of the Flame Retardants In Plamentioning

confidence: 99%

“…ItaP is a biobased flame retardant polyester of the DOPO adduct of dimethyl itaconate and ethylene glycol, which already showed good flame retardant effects in various polyesters, but was not investigated in PLA yet. [30,31]…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Polymeric Acrylate-Based Flame Retardants Containing Two Phosphorus Groups in Different Chemical Environments and Their Influence on the Flammability of Poly (Lactic Acid)

et al. 2020

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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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“…A reaction could not be observed under various conditions, in most cases the BPPO ring opened. For SU-BPPO and DMI-BPPO, the synthesis of oligomers with different diols, as outlined before for DOPO derivatives [38], was also examined (Table S2). These experiments were not successful and they showed ring opening of the BPPO phosphonate ring.…”

Section: Resultsmentioning

confidence: 99%

Improving the Flame Retardance of Polyisocyanurate Foams by Dibenzo[d,f][1,3,2]dioxaphosphepine 6-Oxide-Containing Additives

et al. 2019

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A series of new flame retardants (FR) based on dibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide (BPPO) incorporating acrylates and benzoquinone were developed previously. In this study, we examine the fire behavior of the new flame retardants in polyisocyanurate (PIR) foams. The foam characteristics, thermal decomposition, and fire behavior are investigated. The fire properties of the foams containing BPPO-based derivatives were found to depend on the chemical structure of the substituents. We also compare our results to state-of-the-art non-halogenated FR such as triphenylphosphate and chemically similar phosphinate, i.e. 9,10-dihydro-9-oxa-10- phosphaphenanthrene-10-oxide (DOPO), based derivatives to discuss the role of the phosphorus oxidation state.

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Phosphorus‐Containing Polymer Flame Retardants for Aliphatic Polyesters

Cited by 16 publications

References 41 publications

Synthesis of Novel Polymeric Acrylate-Based Flame Retardants Containing Two Phosphorus Groups in Different Chemical Environments and Their Influence on the Flammability of Poly (Lactic Acid)

Synthesis of Novel Polymeric Acrylate-Based Flame Retardants Containing Two Phosphorus Groups in Different Chemical Environments and Their Influence on the Flammability of Poly (Lactic Acid)

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

Improving the Flame Retardance of Polyisocyanurate Foams by Dibenzo[d,f][1,3,2]dioxaphosphepine 6-Oxide-Containing Additives

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