Dyes based on 5,10-dihydrophenophosphazine. Part 1: disazo direct dyes

Bello, K. A.; Shen, Kaihua; Zhao, Defeng; Esancy, Michelle K.; Freeman, Harold S.

doi:10.1016/s0143-7208(00)00044-9

Cited by 14 publications

(6 citation statements)

References 8 publications

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“…Major properties that have been observed as indices of reduced mutagenicity and genotoxicity is the presence of ring substituents ortho to both the amino group of precursor amine (Gong et al, 2002) as well as bulky alkoxyl groups ortho to the azo linkage (Bello et al, 2000). In case of 4-carboxyl-2,6dinitrophenylazohydroxynaphthalenes, the ortho nitro groups and the azo-hydrazone tautomerism will affect their biological response.…”

Section: Discussionmentioning

confidence: 99%

Genotoxicity evaluation of 4-carboxyl- 2,6-dinitrophenylazohydroxynaphthalenes in mice

et al. 2012

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A short-term in vivo genotoxicity evaluation of 4-carboxyl-2,6-dinitrophenylazohydronaphthalenes (AZ-01 to AZ-04) has been carried out in mice. Aqueous colloidal solutions of the dyes were administered to mice on each day for 5 successive days using gastric gavages. Two end point assessments of the genotoxicity potentials of the dyes were assessed using comet assay and chromosomal aberration studies using the mice bone marrow cells. The dyes were well tolerated at the doses investigated, as there were no deaths or any adverse pharmacotoxic events. Dose-dependent DNA damage (in terms of percentage of tail DNA and Olive tail moment) occurred with AZ-01 and AZ-02, although the effects were significant only with the highest doses. AZ-03 gave similar patterns with those of AZ-01 and AZ-02, while replacement with butanone in AZ-04 altered the observed pattern. Minimal chromosomal damages were obtained for the four dyes, with AZ-01 and AZ-02 giving nonsignificant damages, while the highest dose of AZ-03 produced significant aberrations in terms of breaks. Some minor isochromatid breaks and gaps were also noticed in the dye-treated mice. Mitotic indices in all cases were not significantly different from concomitantly administered vehicle control showing lack of cytotoxicity of the monoazo dyes at these doses. The monoazo dyes show the potential of being utilized as colorants, pending further required tests.

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Section: Discussionmentioning

confidence: 99%

Genotoxicity evaluation of 4-carboxyl- 2,6-dinitrophenylazohydroxynaphthalenes in mice

et al. 2012

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“…The synthesis of DPPA was carried out according to the reported procedure. 23,24 A mixture of 0.30 mol diphenylamine and 0.32 mol PCl 3 was stirred at room temperature for 30 min. The reaction mixture was then slowly heated to 210 C and kept for another 7 h. The reaction vessel was cooled to room temperature and ushed with N 2 to remove HCl and residual PCl 3 .…”

Section: Synthesis and Characterization Of Dppamentioning

confidence: 99%

Intumescent flame retardancy of a DGEBA epoxy resin based on 5,10-dihydro-phenophosphazine-10-oxide

et al. 2015

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5,10-Dihydro-phenophosphazine-10-oxide(DPPA) served as a co-curing agent of 4, 4'-diaminodiphenylmethane for the curing reaction of bisphenol A diglycidyl ether (DGEBA) epoxy resin (EP). 1 H NHR spectrum tracking the reaction process of DPPA with DGEBA revealed that P-H bond of DPPA had the higher reactivity than its N-H bond for reacting with epoxy group. DPPA could promote the curing reaction of DDM with DGEBA. DPPA endowed epoxy resin with high flameretardant efficiency due to the unique combination of phosphorus and nitrogen in the phenophosphazine ring. The cured epoxy resin could pass V-0 rating of UL-94 test with limiting oxgen index (LOI) of 33.6% at only 2.5 wt% DPPA. The reduced peak heat release rate and total heat release, and increased char yield further verified the excellent flame retardancy for EP. Flame-retardant mechanism of the epoxy resin was investigated by thermogravimetry-fourier transform infrared spectrometry (TG-FTIR), scanning electron microscopy, element analysis and FTIR spectrometry. The results indicated that DPPA catalyzed epoxy resin matrix to form the rigid intumescent char and to generate the blowing-out effect.

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“…In the synthesis of compound 1, increasing the isomerisation time to 90 min at 120°C differed from the reported method [11], with hydrolysis beginning at 100-110°C without separating the 10-chloro-5, 10 intermediate taking place at 60-80°C. Compound 2 was prepared via a nitration of compound 1.…”

Section: Resultsmentioning

confidence: 92%

“…In the synthesis of compound 1 , increasing the isomerisation time to 90 min at 120°C differed from the reported method , with hydrolysis beginning at 100–110°C without separating the 10‐chloro‐5,10‐dihydrophenophosphazine intermediate with ethanol, and oxidisation of the hydrolysate of the 5,10‐dihydro‐10‐hydroxyphenophosphazine intermediate taking place at 60–80°C. Compound 2 was prepared via a nitration of compound 1 .…”

Section: Resultsmentioning

confidence: 95%

Synthesis and application of a novel, triphendioxazine‐based, phosphorus‐containing acid dye for wool

Cui

Zhang

2018

Coloration Technology

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A novel phosphorus-containing acid dye based on triphendioxazine was designed and synthesised from diphenylamine through a series of reactions. The dye has a navy-blue colour, high molar extinction coefficient of 5.32 9 10 4 l/molÁcm, and high substantivity for dyeing wool in a salt-free, aqueous dyebath. A high exhaustion value of 98.2% on wool fabrics was recorded at 3% omf and a liquor ratio of 1:20. The wash fastness values of the acid dye, including colour change and staining on cotton and wool, were grades 5, 4 and 4-5, respectively. The dry and wet fastness are grades 4-5 and 4, respectively. In addition, light fastness reaches grades 6-7 at 3% omf dye concentration. These dye properties are better than those of commercial triphendioxazine dyes, for example, CI Direct Blue 106 and CI Reactive Blue 198, under analogous dyeing conditions.

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Dyes based on 5,10-dihydrophenophosphazine. Part 1: disazo direct dyes

Cited by 14 publications

References 8 publications

Genotoxicity evaluation of 4-carboxyl- 2,6-dinitrophenylazohydroxynaphthalenes in mice

Genotoxicity evaluation of 4-carboxyl- 2,6-dinitrophenylazohydroxynaphthalenes in mice

Intumescent flame retardancy of a DGEBA epoxy resin based on 5,10-dihydro-phenophosphazine-10-oxide

Synthesis and application of a novel, triphendioxazine‐based, phosphorus‐containing acid dye for wool

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