W-Phenylenediamine

Ten years ago, good model systems were found for epoxy networks. These were polymers based on monomeric diglycidyl ethers of some bisphenols cured by simple aromatic amines (primarily w-phenylenediamine — wPhDA). Polymers based on these reactants satisfied the requirements for such a model system in several points ... 

All the reactants are individual compounds of high chemical purity with epoxy equivalent close to theoretical values. It has been shown 6,7,16,17) that, at Tcure iS 110-120 °C and especially with diglycidyl ether of resorcinol (DGER) or Bis-phenol-A (DGEBA) and w-phenylenediamine (w-PhDA) as reactants, Eq. (I) proceeds practically without side reactions and yields a polymer with a chemical structure very close to that shown in above. Using different initial ratios of reactants (P = [NH]0/[EP]0 molar ratio), one can prepare a family of polymers with rather broad variations of crosslink concentration per unit volume or number of unreacted groups of different type and properties of the final products. 

Magnesium, calcium, barium, and strontium can also be determined by ion chromatography with w-phenylenediamine in perchloric acid as the eluent. Ion chromatography by conductimetric detection has been described, and applications to environmental waters have been discussed (1,22—23). 

The following compounds are reported to have been deaminated by decomposing their stabilized diazonipm salts aniline o-, m-, and p-toluidine o-, m-, and p-anisidine o-, m-, and p-nitroaniline 2-methoxy-4-nitro-5-aminotoluene > > w-phenylenediamine 7 -tolyl-enediamine p-aminophenol benzidine a- and /S-naphthylamine. - f... 

Some of the earliest dyes prepared by this reaction were Bismarck Brown In 1865, and Chrysoidine G in 1876. The latter is very simple in structure and was obtained by coupling diazotized aniline with w-phenylenediamine... 

The condensation product 7 of w-phenylenediamine and 2-formylcy-clohexanone, on treatment with polyphosphoric acid (PPA), gave the octahydrobenzophenanthroline 8, which, on dehydrogenation, afforded... 

Cl Direct Black 22 [6473-13-8] (Cl 35435) is an example of a tetrakisazo dye, (4,4kdiaminodiphenylamine-2-sulfonic acid bisdiazotized and coupled to 2 mol gamma acid which is then bisdiazotized and coupled to 2 mol w-phenylenediamine) which had production of 552 t in 1985. 

Basic Orange 1 (130) (aniline coupled to 2,4-diaminotoluene) and Basic Orange 2 (22) (aniline coupled to w-phenylenediamine) are examples of amine salt type cationic azo dyes. The cation is formed by protonation under acidic conditions. Under neutral or alkaline conditions, these dyes behave more like disperse dyes. In 1988 the U.S. production of Cl Basic Orange 2 amounted to 132 tons. 

Oiaminophenol. 4-Hydroxy-w-phenylenediamine [95-86-3] (12) forms leaflets that darken on exposure to ait. It is soluble in acid, alkali, ethanol, and acetone and is sparingly soluble in chloroform, diethji ether, and ligroin. 2,4-IDiaminophenol usually is sold as the sulfate [74283-34 ] (Diamol) or dihydtochlotide salt [137-09-7] (Acrol, Amidol). 2,4-Diaminophenol can be prepared from 2,4-dinitrophenol by catalytic hydrogenation or, less conveniendy, by metal reduction in acid solution (Bfichamp method) (169,170). Alternatively, electrolytic reduction and subsequent hydroxjiation of 1,3-dinitrobenzene or 3-nitroaniLine in sulfuric acid can be undertaken (171,172). 

DuPont s w-aramid polymer, MPDI, is polymerized using essentially a 1 1 molar ratio of w-phenylenediamine and isophthaloyl chloride [85]. Patent literature indicates that the fiber, Nomex, is spun directly from the polymerization solution in DMAc, which contains caldum chloride. MPDI polymer solutions containing >3% by weight calcium chloride are quite stable [2]. 

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