Applications of 4,4'-Diaminodiphenylsulfone

4,4'-Diaminodiphenylsulfone (dapsone,DDS) is a diamine-based hardener that is used to cure epoxy-based resins. 4,4′-diaminodiphenylsulfone, is the most common drug prescribed to treat Hansen disease patients. In addition to its antibacterial activity, 4,4'-Diaminodiphenylsulfone has been reported to be involved in other cellular processes that occur in eukaryotic cells^[1].

Fig 1. Chemical structure formula of 4,4'-Diaminodiphenylsulfone

Tetrafunctional epoxy resins can be blended with 4,4'-Diaminodiphenylsulfone and can be thermally cured which can be used in oil field applications. 4,4'-Diaminodiphenylsulfone can also be used to cure iron oxide (Fe2O3) layer double hydroxide based epoxy that forms a flame retardant epoxy nanocomposites. 4,4'-Diaminodiphenylsulfone can also be used as a hardener to cure bisphenol A (DGEBA) for use in the fabrication of flame retardant epoxy/clay nanocomposites[2-4].

4,4'-Diaminodiphenylsulfone is a sulfone active against a wide range of bacteria but mainly employed for its actions against mycobacterium leprae. Antibacterial 4,4'-Diaminodiphenylsulfone is an antibacterial most commonly used in combination with rifampicin and clofazimine as multidrug therapy (MDT) for the treatment of Mycobacterium leprae infections (leprosy). 4,4'-Diaminodiphenylsulfone antagonized all of the I/R end points measured, showing a remarkable ability to decrease markers of damage through antioxidant, antiinflammatory, and anti-apoptotic effects[5]. As an antibacterial, 4,4'-Diaminodiphenylsulfone inhibits bacterial synthesis of dihydrofolic acid, via competition with para-aminobenzoate for the active site of dihydropteroate synthetase. 4,4'-Diaminodiphenylsulfone has anti-inflammatory and immunomodulatory effects[6].

4,4'-Diaminodiphenylsulfone is a sulfone active against a wide range of bacteria but mainly employed for its actions against mycobacterium leprae, which has anti-inflammatory and immunomodulatory effects.

4,4′-Diaminodiphenyl sulfone has been widely used in broad areas in chemistry, as an antileprotic, a curing agent of epoxy resins, and a monomer for preparing polyimide. Various compounds and polymers have also been derived from 4,4′-Diaminodiphenyl sulfone by exploiting the reactivity of its terminal primary amine. Silylated 4,4′-Diaminodiphenyl sulfone prepared in situ has been used as an active monomer for synthesis of aromatic polyamides. However, there are no reports on the synthesis and characterization of 4,4′-Diaminodiphenyl sulfone derivatives with silyl substituents on nitrogen atoms, because of the difficult isolation and purification arising from the sensitivity of the Si–N bond to moisture[7].

4,4'-Diaminodiphenylsulfone can neutralize acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides. Incompatible with strong oxidizing agents. Also incompatible with epoxy resins under uncontrolled conditions. 

References

[1] Sung Chun Cho, Moon Cheol Park, Bhumsuk Keam, Jung Min Choi, Yunje Cho, Soonsil Hyun, Sang Chul Park, and Junho Lee PNAS November 9, 2010 107 (45) 19326-19331.
[2] A novel high performance bismaleimide/diallyl bisphenol A (BMI/DBA)-epoxy interpenetrating network resin for rigid riser application. Jena RK, et al. Royal Society of Chemistry Advances 5(97), 79888-79897, (2015).
[3] Synthesis of a Fe3O4 nanosphere@ Mg-Al layered-double-hydroxide hybrid and application in the fabrication of multifunctional epoxy nanocomposites. Kalali EN, et al. Industrial & Engineering Chemistry Research 55(23), 6634-6642, (2016).
[4] Study of Thermal Stability and Flame Retardancy of Epoxy/clay Nanocomposites Containing Triphenyl Phosphate and Zinc Stannate. Jangra P and Dahiya JB Industrial & Engineering Chemistry Research 7(8), 626-633, (2017)

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