4,4*-Diaminodiphenylmethane

COLIPOSITEIvL TERLALS - POLYMER-MATRIX - THERMOSETS] (Vol 7) Glycidated polyamine (N,NHyHy-tetragl ycidyl-4,4y-diaminodiphenylmethane [28768-32-3]... 

Fig. 1. Structures of commercial epoxy resins (a) phenolic novolac epoxy resin, (b) glycidated polybasic acid, (c) glycidated polyamine (A,A,A, A -tetraglycidyl-4,4 -diaminodiphenylmethane [28768-32-3] (TGMDA)), and (d) glycidated bisphenol A.

The BMT-biiilding blocks primarily used in commercial bismaleimide resins are 4,4 -bismaleimidodiphenylmethane, 2,4-bismaleimidotoluene [6422-83-9] 1,3-bismaleimidobenzene [3006-93-7J, and, sometimes, aUphatic BMIs based on alkanes. However, because of toxicity problems associated with MO A (4,4 -diaminodiphenylmethane) and other diamines with only one or two aromatic rings, polyaromatic diamines and BMIs based on them ate... 

A biphenyl diglycidyl ether based epoxy resin was crosslinked with aminecuring agents (d -diaminodiphenylmethane and aniline novolac) and phenolcuring agents (phenol novolac and catechol novolac), and the thermomechanical... 

By contrast with tertiary amines used in catalytic quantities, primary and secondary amines or acid anhydrides may be used to bring about the cure of epoxy resins by reaction in stoichiometric proportions. A typical amine curing agent used at this level is diaminodiphenylmethane (DDM), which reacts with an individual epoxy-group in the way shown in Reaction 4.17. 

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]... 

The most important starting materials for process A are 4,4, 4"-triamino-triphenylmethane, pararosaniline (119), and parafuchsin (118). Aniline and formaldehyde are treated at 170°C to form, apart from some formaldehyde-aniline intermediates, 1,3,5-triphenylhexahydrotriazine as the main component. Subsequent treatment with an acidic catalyst, for instance with hydrochloric acid, in excess aniline as a solvent initially affords 4,4 -diaminodiphenylmethane, which is finally oxidized to yield parafuchsin (118). Iron(III)chloride and nitrobenzene, which in the past were used as oxidants, are no longer used. The reaction is now performed by air oxidation in the presence of vanadium pentoxide as a catalyst. 

The technically important new fuchsine synthesis from a primary aromatic amine and formaldehyde falls, in the case of aniline, into the above reaction scheme since the formation of the intermediate product, p-diaminodiphenylmethane, is readily intelligible. 

Trippel-Schulte P, Zeiske J, Kettrup A. 1986. Traee analysis of seleeted benzidine and diaminodiphenylmethane derivatives in mine by means of liquid ehromatography using preeolumn sample preconcentration, UV and electrochemical detection. Chromatographia 22(1-6) 138-148. 

Naphthylamine, 4-aminodiphenyl, 4-chloro-2-toluidine, benzidine, 2,4,5-trimethylaniline, 2,4-diaminoanisol, 2,4-toluylenediamine, 2-amino-4-nitrobenzene, 3,3 -dichlorobenzidine, 3,3 -dimethoxybenzidine, 3,3 -dimethylbenzidine, 3,3 -4,4 -diaminodiphenylmethane, 4,4 -diaminodiphenybnethane, 4,4 -methylene-bis-(2-chloroaniline), 4,4 -Oxydianiline, 4,4 -thiodianiline, 2-aminoazotoluene,... 

Table 6.1 Polycondensation of terephthalic acid, TPA, and 4,4 -diaminodiphenylmethane, MDA, in the presence of poly(4-vinylpyridine) in N-methylpyrrolidone-pyridine solvent. [Reprinted from N. Yamazaki and F. Higashi, Adv. Polym. Sci., 38,1 (1981)]...

In diamines such as 4,4 -diaminodiphenylmethane, 4,4 -diaminodiphenyl sulphone or 1,6-hexamethylenediamine, the substitution effect is practically absent641 although this may not be the case for di- and polyamines where the distance between the amino groups is not large allowing inductive and steric effects to be operative 59,68 ... 

The imino-, oxo- and 4,4 -diaminodiphenylmethane-A,A -diacetates have been isolated from aqueous solution (Table 28). The central nitrogen or oxygen atoms of these diacetate groups are probably bonded to the metal as found for the pyridine-2,6-dicarboxylates. 

Diaminodiphenyl sulfone (DDS) cured tetraglycidyl-4,4 -diaminodiphenylmethane (TGDDM) epoxies are the mpst common composite matrices utilized in high performance fibrous composites prepared from prepregs. The structures of the unreacted TGDDM epoxide and DDS monomers are illustrated in Fig. 3. The TGDDM epoxide monomer is a liquid at 23 °C, whereas the DDS monomer is a crystalline... 

The cure of tetra-N-glycidyl-4,4 -diaminodiphenylmethane (TGDDM), as a commercial grade, with 4,4 -diaminodiphenylsulphone (DDS) has been studied by Barton 89), in the temperature range 170-220 °C. The data were fitted to Eq. (4-11) with m = 1 and n = 1 or 2. 

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