- (Solid?+?Liquid) Phase Equilibria of 1,2-Bis(2-oxo-5,5-dimethyl-1,3,2-dioxyphosphacyclohexyl-2-imino)ethane in Nine Pure Solvents
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1,2-Bis(2-oxo-5,5-dimethyl-1,3,2-dioxyphosphacyclohexyl-2-imino)ethane (BODIE) was synthesized and characterized by elemental analysis, mass spectra, infrared spectroscopy and nuclear magnetic resonance. The thermostability of BODIE was measured by thermogravimetric analysis and the melting temperature and the fusion enthalpy of BODIE were determined by using a differential scanning calorimeter. A gravimetric method was applied to measure the solubilities of BODIE in the selected solvents. The solubility data of BODIE in selected organic solvents are well fitted by the modified Apelblat model. Also, the solubility parameter of BODIE was estimated by the Scatchard–Hildebrand model. The results show that these models can satisfactorily reproduce the experimental data.
- Han, Feng,Pei, Liangjun,Xue, Fengfeng,Li, Dong
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- Synthesis of novel phosphorus-based flame retardants containing 9,9-bis (4-hydroxyphenyl) fluorine and their reinforcements on the fire safety of polypropylene
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Fabricating an effective synergism to improve the flame-retardant (FR) efficiency is recently considered to be a very promising way to prepare high-efficient FRs system. A novel FRs containing phosphorus and (4-hydroxyphenyl) fluorene have been synthesized and characterized by FTIR, 1H NMR and MS. The FRs were then incorporated into polypropylene (PP) in different ratios, and then, ammonium polyphosphate (APP) was added to the FRs/PP system, with subsequent investigation into the synergistic effects between FRs and APP. Limited oxygen index (LOI), UL-94 test and cone calorimeter test were adopted to investigate the FR properties of the flame-retardant PP composites. The LOI value is as high as 31.0%, when FRs/APP is 2/3. Moreover, due to the synergistic FR effects between FRs and APP, the pHRR of PP7 decreases from 783?kW?m?2 (PP0) to 110?kW?m?2 (PP7), which is 85% lower than those of PP. Meanwhile, thermogravimetric analysis (TG) was used to study the thermal degradation characteristics of the PP composites. The char residues increased from 0.02 mass% to 15.85 mass% at 650?°C when FRs/APP is 3:2, indicating that there are synergistic flame-retarding effects between FRs and APP. Generally, the stable char layers of FR/APP/PP composites are responsible for the improved FRs properties, and the char layers could not only effectively prevent the release of combustion gases from releasing but also hinder the propagation of oxygen and heat into the interior substrate.
- Qian, Xiaodong,Guo, Nan,Zhao, Yanhua,Lu, Lingang,Wang, Huiya,Wang, Xuebao,Jin, Jing,Shao, Gaosong,Hu, Zhijia
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- Waterborne polyurethane conjugated with novel diol chain-extender bearing cyclic phosphoramidate lateral group: Synthesis, flammability and thermal degradation mechanism
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A diol bearing a cyclic phosphoramidate pendant group, namely 2-(5,5-dimethyl-2-oxo-2λ5-1,3,2-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 PNMPD-based 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.
- Zhang, Peikun,Zhang, Zhenyu,Fan, Haojun,Tian, Saiqi,Chen, Yi,Yan, Jun
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- Synthesis and antimicrobial activity of 5,5′-dimethyl-2-oxido-[1,2,3] -dioxaphosphorinane-2-yl-amino carboxylates
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Synthesis of several 5,5-dimethyl-2-oxido-[1, 3,2]-dioxaphosphorinane-2-yl- amino car-boxylates (4a-j) was accomplished through a two-step process. This involves prior preparation of the intermediate monochloride (2), 2-chloro-5,5-dimethyl [1,3,2]dioxaphosphorinane-2-oxide and its subsequent reaction with various amino acid esters (3a-j) in dry tetrahydrofuran in the presence of triethyl amine at room temperature. They were characterized by elemental analysis, IR, 1H, 13C, 31P NMR, and mass spectral data. Their antifungal and antibacterial activity is also evaluated. Majority of these compounds exhibited moderate antimicrobial activity in the assay.
- Hari Babu,Syam Prasad,Suresh Reddy,Naga Raju
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- Synthesis and thermal properties of two novel P-N compounds
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Two novel P-N compounds were synthesized through a two-step reaction including the synthesis of 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane-2-oxide (M) and its reaction with 2,2,6,6-tetramethylpiperidine-4-amine and N-butyl-2,2,6,6-tetramethylpiperidin-4-amine. The structures were confirmed by NMR (1H, 13C, 31P), FT-IR and MS. Their thermal properties were also evaluated by thermogravimetric analysis (TGA). The TG curves showed that the two compounds have residues of 4.9 and 1.1 wt % at 600 °C and the temperature of maximum weight loss rate (Tmax) was 292 and 255 °C, respectively.
- Wei, Shanshan,Chen, Ligong,Li, Yang
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- Phosphorus-nitrogen type flame retardant as well as preparation method and application thereof
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The invention discloses a novel phosphorus-nitrogen type flame retardant and a preparation method thereof, and relates to the technical field of flame retardants, and the structural formula of the phosphorus-nitrogen type flame retardant is as shown in the formula I. The preparation method of the phosphorus-nitrogen type flame retardant comprises the following steps: reacting an intermediate neopentyl glycol phosphoryl chloride with imidazole, cooling to room temperature after the reaction is completed, and carrying out suction filtration, water washing, reduced pressure rotary evaporation and drying to obtain the phosphorus-nitrogen type flame retardant; and blending the phosphorus-nitrogen flame retardant solution and the ripened viscose liquid to prepare a flame-retardant viscose spinning solution, forming in a coagulating bath, and drafting, washing and drying to obtain the phosphorus-nitrogen flame-retardant viscose fiber. The phosphorus-nitrogen type flame retardant prepared by the invention contains a nitrogen element, can play a flame retardant role when a condensed phase and a gas phase are used, and is simple in synthesis process, and is halogen-free, formaldehyde-free, environment-friendly and pollution-free; the prepared phosphorus-nitrogen type flame-retardant viscose fiber overcomes the defect that the existing viscose fiber is easy to burn, avoids the problems of poor durability, serious strength damage and the like, and improves the flame retardance of the viscose fiber.
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Paragraph 0034-0036; 0046-0048; 0057-0059; 0068-0070
(2021/08/14)
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- Regio- And Stereoselective Addition of Bronsted Acids to Yndiamides: Synthesis of N, O, N - And N, S, N -Trisubstituted Ketene Acetals
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Yndiamides, N,N-disubstituted alkynes, are versatile building blocks for the synthesis of nitrogen-containing organic molecules. Unlike ynamides, relatives that are inherently polarized by a single nitrogen substituent, their pseudo-symmetric nature renders regioselective reactions challenging. Here we report investigations into the regioselective addition of Br nsted acids to non-symmetric yndiamides, a reaction that delivers N,O,N- and N,S,N-trisubstituted ketene acetals with excellent regio- and stereoselectivity.
- Anderson, Edward A.,Garry, Olivia L.,Mansfield, Steven J.
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p. 4221 - 4230
(2021/10/04)
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- A phosphorus-nitrogen intumescent fire retardant and its preparation method
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The invention relates to a phosphorus-nitrogen intumescent flame retardant and a preparation method thereof. The preparation method comprises the steps: mixing neopentyl glycol and a solvent, adding a catalyst, dissolving the catalyst, then, adding phosphorus oxychloride into a reaction solution under the condition of stirring at the temperature of 0-10 DEG C, reacting for 4-8 hours at the temperature of 20-50 DEG C after phosphorus oxychloride is added completely, removing the solvent through distilling after reacting ends, and washing and drying residues, so as to obtain cyclic phosphoryl chloride; adding the obtained cyclic phosphoryl chloride and an acid binding agent into a solvent, stirring to dissolve, adding diamine into a reaction solution under the condition of stirring at the temperature of 15-30 DEG C, then, reacting for 8-12 hours at the temperature of 50-110 DEG C, removing the solvent through distilling after reacting ends, and washing and drying residues, thereby obtaining the phosphorus-nitrogen intumescent flame retardant. The phosphorus-nitrogen intumescent flame retardant and the preparation method thereof have the advantages that the synthesis process is simple, the reaction time is short, the product has a melting point, the transparency is good when the flame retardant is added into materials, the flame-retardant effect is good, the influence on mechanical properties is low, and the like; and meanwhile, the disadvantage that intumescent flame retardants cannot be applied to the flame retardance of engineering plastics due to poor thermal stability is overcome.
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Paragraph 0029; 0030; 0045; 0047; 0049; 0051
(2018/01/09)
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- Phosphaphenanthrene phosphate flame retardant with xenyl and preparation method and application thereof
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The invention provides a phosphaphenanthrene phosphate flame retardant with xenyl and a preparation method. The preparation method comprises the steps that phenyl-P-benzoquinone and DOPO react to generate an intermediate I; neopentyl glycol and phosphorus oxychloride synthesize an intermediate II under the effect of chloroform; triethylamine is used as an acid-binding agent, N,N-dimethyl formamide (DMF) is used as a solvent, and the intermediate I and the intermediate II react to obtain the phosphaphenanthrene phosphate flame retardant with the xenyl. The appearance of the flame retardant is white powder, the initial decomposition temperature is about 315 DEG C, weightlessness reaches 10% at the temperature of 420 DEG C, and the carbon residue rate of the flame retardant reaches 39% at the temperature of 700 DEG C. The flame retardant has the good heat stability and high carbon residue rate, and can be used for ABS halogen-free flame retardance.
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Paragraph 0025; 0028; 0030
(2016/10/10)
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- PROCESSES FOR PRODUCTION OF CYCLIC ALKYLENE PHOSPHOHALIDATE AND CYCLIC PHOSPHORIC ACID ESTER
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A process for producing a cyclic alkylene phosphorohalidite, which comprises reacting a specific phosphorus trihalide with a specific alkylene glycol compound under conditions where the phosphorus trihalide is present in an excess amount relative to the amount of the alkylene glycol compound in the reaction system to order to obtain the cyclic alkylene phosphorohalidite by reacting the alkylene glycol compound with the phosphorus trihalide; and a process for producing a cyclic phosphoric acid ester by using the obtained cyclic alkylene phosphorohalidite as a raw material.
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Page/Page column 8-9; 13
(2012/09/21)
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- Synthesis of new organophosphorus compounds using the atherton-todd reaction as a versatile tool
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This article discusses the behavior of seven organophosphorus compounds under Atherton-Todd conditions. Therefore, the reactivity and selectivity of different (phen)oxaphosphinines, dioxaphosphinines, dioxaphosphinanes, and diphenylphosphine oxide with three nucleophiles were systematically studied. The results prove the versatility of the Atherton-Todd reaction to a broad range of organophosphorus compounds with different phosphorus environments and reactive Pi-H bonds. The nucleophiles studied in this article were chosen as model substrates for amines and alcohols. Because organophosphorus molecules are important and versatile compounds, for a broad field of applications, novel synthetic approaches are of interest to both academia and industry. As an example, the single-step synthesis of the bridged 1,3-phenylene bis(diphenylphosphinate) with potential flame-retardant properties was added to this study. In addition, the reaction is utilized for the synthesis of a novel organophosphorus anhydride.
- Wagner, Sebastian,Rakotomalala, Muriel,Bykov, Yana,Walter, Olaf,Doering, Manfred
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scheme or table
p. 216 - 222
(2012/07/13)
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- PHOSPHORUS COMPOUND, USE THEREOF AND FLAME-RETARDANT POLYESTER FIBER
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A phosphorus compound represented by the formula (I): wherein R1 and R2 are, the same or different, a hydrogen atom, a straight or branched-chain alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 12 carbon atoms which may be optionally substituted for an alkyl group having 1 to 4 carbon atoms, R3, R4, R5, R6 and R7 are, the same or different, a hydrogen atom or an aryl group having 6 to 12 carbon atoms which may be optionally substituted for an alkyl group having 1 to 4 carbon atoms, or R3 and R4, R4 and R5, R5 and R6 or R6 and R7 may form a 6 membered ring with carbon atoms wherein these groups bond a benzene ring provided that R3, R4, R5, R6 and R7 are not hydrogen atoms at the same time.
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Page/Page column 9; 14-15
(2008/12/05)
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- PHOSPHORAMIDE ESTER FLAME RETARDANT AND RESINS CONTAINING SAME
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Certain cyclic phosphoramide ester compounds useful, inter alia, as halogen-free flame-retardant compounds, are disclosed. The compounds are particularly useful for providing flame retarded polyurethane foams. (I)
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Page/Page column 9-10
(2008/12/07)
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- METHOD FOR PRODUCING PHOSPHORUS COMPOUND HAVING PHOSPHATE-PHOSPHONATE BOND
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A novel process for preparing in a high purity and in a high yield phosphorus compounds having a phosphate-phosphonate bond within one molecule, along with only a small amount of a by-product, without being restricted by the kind of a phosphonate having an alcoholic hydroxyl group which is a raw material, without using a catalyst such as magnesium chloride, but only using a nitrogen-containing basic compound.
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Page/Page column 13-14; 17
(2008/06/13)
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- Dialkylphosphates as stereodirecting protecting groups in oligosaccharide synthesis
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(Chemical Equation Presented) Double duty: A phosphoric ester at the C2 position in glycosyl donors directs the glycosylation to occur selectively at the anomeric carbon atom with complete 1,2-trans selectivity. Since the phosphoric ester can be removed to give the hydroxy function, this group serves as a stereodirecting protecting group in oligosaccharide synthesis.
- Yamada, Takeshi,Takemura, Kazunobu,Yoshida, Jun-Ichi,Yamago, Shigeru
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p. 7575 - 7578
(2008/02/01)
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- ORGANOPHOSPHORUS COMPOUND HAVING PHOSPHATE-PHOSPHONATE BOND, AND FLAME-RETARDANT POLYESTER FIBER AND FLAME-RETARDANT POLYURETHANE RESIN COMPOSITION EACH CONTAINING THE SAME
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The present invention provides a phosphate-phosphonate compound which has a low volatility and a high phosphorus content, does not exert adverse influences on the physical properties of a product containing the phosphate-phosphonate compound as a material, and is recyclable and causes substantially no environmental load since a halogen atom such as a chlorine atom or a bromine atom is not included. A phosphorus compound containing a phosphate-phosphonate bond in one molecule and having a specific structure has a high flame retarding property. By using a phosphate-phosphonate compound as a flame retarding agent for a polyurethane or for a polyester, preferable plasticity and flame retarding property are obtained. Such a flame retardant agent exerts substantially no adverse influences on the physical properties of a polyurethane foam or a polyester fiber.
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Page/Page column 40
(2008/06/13)
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- Synthesis and reactivity of O-acyl selenophosphates
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The synthesis of several new O-acyl selenophosphates were investigated. The stability and reactivity of the products were studied and related to their structure. The Royal Society of Chemistry 2005.
- Rachon, Janusz,Cholewinski, Grzegorz,Witt, Dariusz
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p. 2692 - 2694
(2007/10/03)
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- Synthesis and fugicidal activities of 2-silatranyl propylamino-4-substitued phenyl(hydrogen)-5,5-dimethyl-1,3,2-dioxaphosphinanes-2-oxides (sulfides)
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Phosphoryl-aminopropyl-silatranes 4 were synthesized by nucleophilic reactions of 2-Cl-1,3,2- dioxaphosphinanes 2 with α-aminopropyl-silatrane 3, which was obtained by the cyclization reaction of triethanolamine and γ-aminopropyltriethoxysilane. The structures of the products were characterized by 1H NMR, 31P NMR, IR, MS, and elemental analyses. The target compounds 4 exhibited fungicidal activity. Copyright Taylor & Francis Inc.
- Wan, Shi-Guan,Yang, Xing-Yu,Yu, Yan,Liu, Chang
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p. 2813 - 2821
(2007/10/03)
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- Phosphorochloridates from phosphorohydrazides with ButOCl: Stereospecificity, selectivity and phosphorylium ion intermediates
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The efficiency with which a six-membered cyclic phosphorochloridate can be obtained from the corresponding hydrazide with retention of configuration at phosphorus, using tert-butyl hypochlorite in tert-butyl alcohol, depends on how stereoelectronic factors influence the fate of an intermediate chloride-phosphorylium ion pair.
- Harger, Martin J.P
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p. 6749 - 6752
(2007/10/03)
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- Reductive cleavage of the halogen-phosphorus, oxygen-phosphorus and phosphorus-phosphorus bonds with alkali metals
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The reduction of phosphorus acid chlorides as well as hypophosphates, pyrophosphates and mixed P(III)-P(V) anhydrides with alkali metals (Li, Na, K) in NH3 liq. / THF solution and potassium naphthalenide was investigated. It was found that this type of phosphorus compounds easily undergo reduction: a) >P(O)Cl to >P(O)H; b) >P(O)P(O)P(O)H; c) >P(O)-O-P(O)P(O)OH and >P(O)H; d) >P(O)-O-PP(O)O- and >P-. The results of our experiments strongly suggest that the mixed P(III)-P(V) anhydride is reduced by potassium naphthalenide in THF with the cleavage of the P(III)-oxygen bond.
- Nycz, Jacek,Rachon, Janusz
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- Synthesis and antimicrobial activity of 2-aryloxy-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxides
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A series of 2-aryloxy-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxides have been synthesized by condensing 2,2-dimethyl-1,3-propanediol with various arylphosphorodichloridates. Some of these compounds are prepared by reacting the monochloride, 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, in situ with some substituted phenols. The monochloride is prepared by condensing 2,2-dimethyl-1,3-propanediol with phosphorus oxychloride. Their structures have been confirmed by elemental analyses, IR, 1H, 13C and 31P NMR and mass spectral studies. All these compounds are screened for their antibacterial activity against Escherichia coli, Klebsiella pneumoniae, Bacillus subtilis and Staphylococcus aureus and antifungal activity against Curvularia lunata, Fusarium oxysporum and Helmeinthosporium oryzae.
- Raghu,Devendranath Reddy
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p. 1228 - 1232
(2007/10/03)
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- 2-Alkyl-5,5-dimethyl-1,3,2-dioxaphosphorinan-2-ones α-Lithiated Carbanions. Synthesis, Stability, and Conformation
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The preparation and a conformational study of lithiated 2-alkyl-5,5-dimethyl-1,3,2-dioxaphosphorinan-2-ones (2) in THF-hexane are described.These anions are present as two rapidly interconverting species with the P=O bond either axial (2a) or equatorial (2e).They are thermally unstable, but can be stabilised by the presence of one equivalent of LiBr or of lithium di-isopropylamide.A 31P NMR study of the self condensation of the carbanions (2) showed that the phosphorus atom in the axial conformation (2a) is more electrophilic than in the equatorial one (2e).An X-ray structural study of 2,5,5-trimethyl-1,3,2-dioxaphosphorinan-2-one is described.
- Patois, Carl,Ricard, Louis,Savignac, Philippe
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p. 1577 - 1581
(2007/10/02)
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