Phosphorus-containing polymers from tetrakis-(hydroxymethyl)phosphonium sulfate<scp>iii</scp>. A new hydrolysis-resistant tris(allyloxymethyl)phosphine oxide and its thiol-ene reaction under ultraviolet irradiation

Tan, Zhiyong; Wu, Chengyan; Zhang, Min; Lv, Wei; Qiu, Jian; Liu, Chengmei

doi:10.1039/c4ra06080f

Cited by 23 publications

(23 citation statements)

References 49 publications

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“…TPOPO was prepared by standard Willamson method with the aid of phase transfer catalyst (PTC) 40 . That is, transformation of hydroxyl group into sodium alkoxide with sodium hydroxide and successive treatment with propagyl bromide.…”

Section: Scheme 2 Synthesis Of Tpopo and Its Thermal Cycloaddition Rementioning

confidence: 99%

“…In this paper, a novel phosphorus-containing trialkynes, namely tris(prop-2-yn-1-yloxy methyl)phosphane oxide(TPOPO), was first prepared in our group. The key starting material, tetrakis (hydroxymethyl) phosphonium sulfate (THPS), has been proved that it is an eco-friendly chemical and was awarded the American Green Chemicals Award in 1997 39,40 . The TPOPO underwent thermal Huisgen cycloaddition reaction [41][42][43][44][45][46] with AzSBO under catalyst-free and solvent-free environment and obtained both phosphorus-and nitrogen-containing thermosets.…”

Section: Introductionmentioning

confidence: 99%

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Phosphorus-containing polymers from THPS. VII. Synthesis of phosphorus-containing trialkynes and their metal-free 1,3-dipolar cycloaddition reaction with azidated soybean-oil

et al. 2016

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A novel hydrolysis-resistant trialkynes, namely tris(prop-2-yn-1-yloxy methyl)phosphane oxide(TPOPO) was prepared from an environmental friendly tetrakis (hydroxymethyl) phosphonium sulfate (THPS). The chemical structure of TPOPO was characterized by FT-IR, NMR ( 1 H, 13 C, 31 P) and MS. The TPOPO underwent metal-free and solvent-free 1,3dipolar cycloaddition reaction with azidated soybean oil (AzSBO) with different alkyne/azide molar ratio. The gel contents of the cured polymers were higher than 95% and the char yields of polymers at 850℃ were over 16.4%. DMA analysis showed the glass transition temperatures were over 45.9 o C. The cured polymers showed high dielectric constant and dielectric loss for their high polarity.

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Section: Scheme 2 Synthesis Of Tpopo and Its Thermal Cycloaddition Rementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Phosphorus-containing polymers from THPS. VII. Synthesis of phosphorus-containing trialkynes and their metal-free 1,3-dipolar cycloaddition reaction with azidated soybean-oil

et al. 2016

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“…For our designed PNMPD monomer, one of the easily hydrolyzable P-O linkage is well-substituted by P-N bond, which shows preferable resistant to hydrolysis. 19 On the other hand, in the PNWPU dispersions, the phosphoramidate is just as a "core" that surrounded by the "shells" of sixth position's hydrophobic methyl groups in NPG and dioxaphosphorinane of PNMPD, conforming to the Newman's "rule of six". 28 Accordingly, these moisture-sensitive moieties are resistant to hydrolyse, which endows the pendant phosphamide groups bearing PNWPU far better hydrolysis stability than previously reported phosphate-based polymers.…”

Section: Hydrolytic Resistance Of Pnwpumentioning

confidence: 99%

Waterborne polyurethane conjugated with novel diol chain-extender bearing cyclic phosphoramidate lateral group: synthesis, flammability and thermal degradation mechanism

Zhang

Fan

et al. 2016

RSC Adv.

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A diol bearing a cyclic phosphoramidate pendant group, namely 2-(5,5-dimethyl-2-oxo-2l 5 -1,3,2-dioxaphosphinan-2-ylamino)-2-methyl-propane-1,3-diol (PNMPD) was synthesized and characterized by FTIR and NMR. Subsequently, PNMPD was applied as a flame-retardant chain extender to prepare phosphorus-nitrogen containing waterborne polyurethane (PNWPU), and the influence of PNMPD on the hydrolysis, thermal and flame-retardant properties of PNWPU was investigated. The fabricated PNMPDbased PNWPU shows controllable mechanical properties and maintains the good hydrolysis-resistance property of polyurethane. Thermal stability and flammability analysis demonstrate that though the covalent conjugation of PNMPD induces a slight thermal destabilization effect, it efficiently promotes char formation in PNWPU, as a result, a 27.2% limiting oxygen index (LOI) value and a UL-94 V-0 rating can be achieved with only 12 wt% PNMPD incorporated. Compared with WPU, the peak heat release rate (PHRR), total heat release (THR), peak smoke production rate (PSPR) and total smoke release (TSR) of PNWPU-12, evaluated with cone calorimetry, are decreased by 44.7%, 39.0%, 42.9% and 36.1%, respectively. In addition, the flame retarding mechanism of PNWPU was comprehensively investigated by SEM microscopy, EDX analysis, real time FTIR and TG-FTIR, and results elucidate that these notable reductions in fire hazards are probably attributed to the formation of polyphosphoric acid-rich rugged and intumescent char in the condensed phase, which behaves as a "labyrinth effect" to effectively inhibit the transmission of heat, oxygen and volatile fragments from entering into the flame zone and shield the underlying PNWPU matrix against flame.

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“…When the phosphorus content was increased to 3%, the peak heat release rate (PHRR) and total heat release (THR) of modified unsaturated polyester resin were reduced by 45.7 and 45.5%, respectively, in comparison with those of pure unsaturated polyester resin. Therefore, it is a good strategy to improve the flame retardancy of EPs through the incorporation of chemical units containing azaphosphorine with PCN bonds into polymer matrixes …”

Section: Introductionmentioning

confidence: 99%

Synthesis of a novel azaphosphorine flame retardant and its application in epoxy resins

Liu

Huang

Zhu

et al. 2017

J of Applied Polymer Sci

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A novel PCN bond containing azaphosphorine, 5‐(4‐hydroxy)anilinomethyl‐1,3‐di(4‐hydroxy)phenyl‐1,3,5‐diazaphosphorinane (ADDPP‐OH), which could be used as both a cocuring agent and a flame‐retarding agent for epoxy resins (EPs), was synthesized from tetrakis(hydroxymethyl)phosphonium sulfate and characterized by FTIR, 1H‐NMR, 13C‐NMR, 31P‐NMR, and so on. Compared with the pure EP, the ADDPP‐OH–EP composites showed increased decomposition temperatures and char yields. When the content of ADDPP‐OH was 10 wt %, the cured EP composite possessed a limiting oxygen index value of 33.7% and passed the V‐0 rating of the UL‐94 test. The mechanical properties of the ADDPP‐OH–EP composites was improved because of the increased crosslinking density. In addition, the morphology of the residual char indicated an intumescent and multiporous structure in the inner space and a compact and continual appearance in the outer layer; this was important in preventing the materials from burning further. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 45721.

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Phosphorus-containing polymers from tetrakis-(hydroxymethyl)phosphonium sulfateiii. A new hydrolysis-resistant tris(allyloxymethyl)phosphine oxide and its thiol-ene reaction under ultraviolet irradiation

Cited by 23 publications

References 49 publications

Phosphorus-containing polymers from THPS. VII. Synthesis of phosphorus-containing trialkynes and their metal-free 1,3-dipolar cycloaddition reaction with azidated soybean-oil

Phosphorus-containing polymers from THPS. VII. Synthesis of phosphorus-containing trialkynes and their metal-free 1,3-dipolar cycloaddition reaction with azidated soybean-oil

Waterborne polyurethane conjugated with novel diol chain-extender bearing cyclic phosphoramidate lateral group: synthesis, flammability and thermal degradation mechanism

Synthesis of a novel azaphosphorine flame retardant and its application in epoxy resins

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