4 : 4 -Diaminodiphenyl

In the presence of acids, hydrazobenzene rearranges to give about 0 per cent, of benzidine (4 4 -diaminodiphenyl) and about 30 per cent, of diphenyline (2 4 -diaminodiphenyl) ... 

The conversion of a hydrazobenzene into a diaminodiphenyl upon treatment with acid is termed the benzidine rearrangement. The following mechanism for the formation of benzidine from hydrazobenzene appears reasonable ... 

Polyimides for use ia molded products and high temperature films can be produced by the reaction of pyromelHtic dianhydride [89-32-7] and 4,4 -diaminodiphenyl ether [13174-32-8] ia DMAC to form a polyamide that can be converted iato a polyimide (13). DMAC can also be used as a spinning solvent for polyimides. AdditionaUy, polymers containing over 50% vinyHdene chloride are soluble up to 20% at elevated temperatures ia DMAC. Such solutions are useful ia preparing fibers (14). 

Technora. In 1985, Teijin Ltd. introduced Technora fiber, previously known as HM-50, into the high performance fiber market. Technora is based on the 1 1 copolyterephthalamide of 3,4 -diaminodiphenyl ether and/ -phenylenediamine (8). Technora is a whoUy aromatic copolyamide of PPT, modified with a crankshaft-shaped comonomer, which results in the formation of isotropic solutions that then become anisotropic during the shear alignment during spinning. The polymer is synthesized by the low temperature polymerization of/ -phenylenediamine, 3,4 -diaminophenyl ether, and terephthaloyl chloride in an amide solvent containing a small amount of an alkaU salt. Calcium chloride or lithium chloride is used as the alkaU salt. The solvents used are hexamethylphosphoramide (HMPA), A/-methyl-2-pyrrohdinone (NMP), and dimethyl acetamide (DMAc). The stmcture of Technora is as follows ... 

The chemical production of aminophenols via the reduction of nitrobenzene occurs in two stages. Nitrobenzene [98-95-3] is first selectively reduced with hydrogen in the presence of Raney copper to phenylhydroxylamine in an organic solvent such as 2-propanol (37). With the addition of dilute sulfuric acid, nucleophilic attack by water on the aromatic ring of /V-phenylhydroxylamine [100-65-2] takes place to form 2- and 4-aminophenol. The by-product, 4,4 -diaminodiphenyl ether [13174-32-8] presumably arises in a similar manner from attack on the ring by a molecule of 4-aminophenol (38,39). Aniline [62-53-3] is produced via further reduction (40,41). 

The first are competitors of PABA (p-aminobenzoic acid) and thus intermpt host de novo formation of the tetrahydrofoUc acid required for nucleic acid synthesis. Examples of dmgs that fall into this group are the sulfones and sulfonamides. The most weU-known of the sulfones is dapsone (70, 4,4 -diaminodiphenyl sulfone, DDS), whose toxicity has discouraged its use. Production of foHc acid, which consists of PABA, a pteridine unit, and glutamate, is disturbed by the substitution of a sulfonamide (stmcturally similar to PABA). The antimalarial sulfonamides include sulfadoxine (71, Fanasd [2447-57-6]) sulfadiazine (25), and sulfalene (72, sulfamethoxypyrazine [152-47-6] Kelfizina). Compounds of this group are rapidly absorbed but are cleared slowly. 

Phenothiophosphine ring-containing polyamides and polyesters were also prepared by the polycondensation of 2,8-bischloroformyl-lO-phenylphenothiophos-phine 5,5, 10-trioxide with aromatic diamines such as 4,4 -diaminodiphenyl ether and 4,4 -diaminodiphenyl-methane, and bisphenols such as 4,4 -dihydroxybiphe-nyl and 4,4 -dihydroxydiphenylmethane, respectively [159]. These polymers are soluble in polar aprotic solvents and also exhibit good heat and fire resistance. Phosphorus containing high performance polymers are shown in Table 6. 

Most analytical work on sulphones has naturally been concerned with the compounds synthesized for special purposes, e.g. sulphonal, trional and tetronal as sedatives and hypnotics Sulphenone (4-chlorodiphenyl sulphone) and Tedion (2,4,4, 5 -tetrachlorodiphenyl sulphone) as acaricides 4,4 -diaminodiphenyl sulphone as an antileprotic. In choosing examples preference has been given to methods devoted to more than a single sulphone. 

Most of the examples concern substituted diphenyl sulphones, with the anti-leprotic agent 4,4 -diaminodiphenyl sulphone taking a prominent place. Cates and Meloan56 separated aliphatic, aromatic and cyclic sulphones using helium carrier gas and thermal... 

CiiHijNj 101-77-9) see Aeriflavinium chloride 4,4 -diaminodiphenyl sultide (C12H12N2S 139-65-1) see Dapsone... 

Michler s base, N,N,N, N -tetramethyl-4,4 -diaminodiphenyl-methane) in 10 ml glacial acetic acid (yields a greenish solution) and make up to 100 ml with 80% 2-propanol. 

Virtually all of the nitrobenzene made is converted to aniline. The most important use of aniline is for the preparation of 4,4 -diaminodiphenyl methane (commonly called methylenedianiline or MDA), an intermediate to one of the main ingredients used to make polyurethane foams and rubber. Aniline is also used to make other rubber chemicals, textile fiber intermediates, dyes, and pharmaceuticals. 

Polyimide-clay nanocomposites constitute another example of the synthesis of nanocomposite from polymer solution [70-76]. Polyimide-clay nanocomposite films were produced via polymerization of 4,4 -diaminodiphenyl ether and pyromellitic dianhydride in dimethylacetamide (DMAC) solvent, followed by mixing of the poly(amic acid) solution with organoclay dispersed in DMAC. Synthetic mica and MMT produced primarily exfoliated nanocomposites, while saponite and hectorite led to only monolayer intercalation in the clay galleries [71]. Dramatic improvements in barrier properties, thermal stability, and modulus were observed for these nanocomposites. Polyimide-clay nanocomposites containing only a small fraction of clay exhibited a several-fold reduction in the... 

Azo dye metabolites Activated sludge Under aerobic conditions, two compounds 4,4 -thiodianiline and p-kresidine were most easily degraded, followed by 4,4 -diaminodiphenylmethane and 2-naphthylamine. Under anaerobic conditions, stabilities of the amines were totally different and compounds p-kresidine, 4,4 -diaminodiphenyl methane, and 2-naphthylamine were degraded while the 4-chloroaniline, 2,4-diaminotoluene, and 2,4-diaminoanisole were partly degraded [16]... 

Historically, bladder tumors have been associated with exposures in the aniline dye industry. However, conclusive evidence for any one particular exposure could not be obtained in these studies since the workers were exposed to many chemicals within the same work area. For example, Case et al. (1954) investigated the incidence of bladder tumors among British workers in the chemical dye industry. In addition to aniline, the workers were exposed to other aromatic amines, including a- and P-naphthylamine, benzidine, and auramine. Although exposures could not be quantified, there was insufficient evidence to suggest that aniline was a cause of bladder cancers. More recent studies indicate that P-naphthylamine, 4-aminodiphenyl, 4-nitrodiphenyl, 4,4-diaminodiphenyl, or o-toluidine may be involved in increased cancers in the dye industry (Ward et al. 1991 Benya and Cornish 1994). 

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