Oxanilides

Oxanilide UV stabilisers of the general form ArNH(C=0)(C=0) NHAr have been known for some time in symmetric [89] and asymmetric [90] forms. Both are available commercially from Clariant as Sanduvor EPU and VSU respectively. Also patented were bis-oxalic acid diamides [91] of basic structure ArNH(C=0)(C=0) NH-R-NH(C=0)(C=0)NHAr. 

While no studies have been found on the efficacy of these additives in aromatic polyesters, their high thermal stability and the absorption peak at 290 nm with a tail only going as far as 350 nm means that they could be useful stabilisers for these polymers. 

Attempts have also been made to produce dual-functional stabilisers incorporating oxanilide and other functional groups. This was achieved by attaching a phenylbenzotriazole unit to one or both of the phenyl rings of the oxanilide [92], or replacing one of these phenyl rings with a phenylbenzotriazole [93] or a hindered piperidine group [94]. 

Later patents to General Electric Company [95, 96] claimed oxanilides which could be used to form polymeric stabilisers or could be added to the polymerisation stage of polycarbonates or polyesters to provide built-in stabilisers. An example of this type of structure IS HOPh-R-PhNH(C=0)(C=0)NHPh-R-PhOH. 

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On nitration, oxanilide yields expl tetra- and hexanitrates (see below)... 

Origin. A.G. Perkins in 1892 obtained TNO directly by heating a soln of finely powdered oxanilide in nitric acid. He also obtained the same compd by the action of a cooled mixt of nitric and sulfuric acids on oxanilide and pptg the product by pouring the soln into w (Ref 2) Impact Sensitivity. PicArsnapp, llmg sample 30 inches... 

J. Kristal, Substitution of Tetranitro Oxanilide and Hexanitro Oxanilide for Tetranitrocarba-zole , PIcArsn Pyrotechnic Research Laboratory Rept 54-TF1-88 (20 Dec 1954) 4) S. Living-... 

Preparation. To prepare Hexanitro-oxanilide, first prepare Tetranitro-oxanilide as described above under the entry 2,4,2 , 4 Tetranitro-oxanilide (TNO) ... 

Man erhalt die Verbindung durch Nitrierung von Oxanilid. Der Stoff ist interessant als relativ hoch-temperatur-stabiler Sprengstoff. 

N 21.96% crysts, mp 295-300°(dec) si sol in hot ale Sc benz very low expin temp. It was prepd by nitrating oxanilide. Its power Sc brisance are comparable with those values of TNT Pb block expansion test — 70% Picric Acid. It is reported to be chemically unstable or reactive with moisture (Refs 6, 7, 8 8t 9) Refs 1) Beil 12, 284, (207) Sc [l65]... 

TB tracer bullet T eNOx or TNO tetr an itro oxanilide... 

Figure 6.15 Chemical structures of some polymer photostabilizers (a) 2-hydroxybenzophenone, (b) hydroxybenzotriazole, (c) oxanilide...

Carboxy deriv, lfts + HzO (from w), at ca 210° converts to oxanilide -3,3-dicarboxylic acid (Ref 2). Other props methods of prepn are given in the refs... 

This substance, m.p. 295-300°, results from the direct nitration of oxanilide.119 It is stable and about as powerful as TNT, and is reported to explode with the production of a temperature which is distinctly lower than that produced by many high explosives. 

Oxanilide and many other carbonaceous materials, incorporated in the grains of colloided powder, yield powders which are flashless in guns of the smaller calibers and, in many cases, are as powerful, weight for weight, as powders which contain none of the inert, or at least non-explosive, ingredients. If nitrocellulose burning in the gun produces 1 mol of carbon dioxide and a certain amount of other gaseous products, then nitrocellulose plus 1 mol of carbon under the same conditions will produce 2 mols of... 

The compound is prepared by the direct nitration of oxanilide (Mixter and Walther [40]). Domanski and Mieszkis [41] investigated the explosive properties of hexanitro-oxanilide and found the following values for the rate of detonation of the pressed product mixed with 2% of dinitrotoluene ... 

This compound is prepared by nitration of oxanilide. It is of interest as being relatively stable at high temperatures. The decomposition reaction above 304 °C is endothermic. 

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