Anilines aniline trimer

Electroluminescence devices derived from aniline trimers, (III), and phenyenediamine derivatives have also been prepared prepared and are described (2), (3). 

Anhydro farm aldehyde aniline Trimeric Methyl-eneaniline or 1,3,5-Triphenyl-trimethylenetri-amine, H C------N(C,H, )--< H,... 

The NH-tt type hydrogen bond between the charged aniline and neutral benzene is deduced by the vibrational spectrum of the [aniline/benzene]4 complex. By using a time-of-flight mass spectrometer with an ion reflector, the intermolecular interactions in aniline/benzene trimer ions were investigated. The NH-7T and N—H N structures of the [aniline/benzene]+ trimer ions based on theoretical calculations are reported in Scheme 19183. 

In this paper, recent results of studies performed on the imide derivatives of the trimeric aniline are presented. Films of TANI-polyimide were also prepared and their electrochemical and electrochromic properties were probed. It is shown from this work that well behaved polymeric materials incorporating aniline trimers can be prepared, these trimers can be addressed electrochemically within such polymeric systems and the behavior of the trimer within the polymer does not differ significantly from that within the model compounds. 

In an electroactive polymer system, Huang et al. (2011) attempted to prepare advanced PCN anticorrosive coating materials with the synergistic effects of redox catalytic capabihty and gas barrier properties by incorporation of well-dispersed organophilic clay platelets into amine-capped aniline trimer (ACAT)-based electroactive polyimide (EPl) matrix through chemical imidization (see Fig. 13.13). 

Huang H.-Y, Huang T. C., Yeh T.-C., Tsai C.-Y, Lai C. L. et al. (2011), Advanced Anticorrosive Materials Prepared from Amine-capped Aniline Trimer-based Electroactive Polyimide-clay Nanocomposite Materials with Syneigistic Effects of Redox Catalytic Capabdity and Gas Barrier Properties. Po/>wier, 52,2391 00. 

Primary aromatic amines react with aldehydes to form Schiff bases. Schiff bases formed from the reaction of lower aUphatic aldehydes, such as formaldehyde and acetaldehyde, with primary aromatic amines are often unstable and polymerize readily. Aniline reacts with formaldehyde in aqueous acid solutions to yield mixtures of a crystalline trimer of the Schiff base, methylenedianilines, and polymers. Reaction of aniline hydrochloride and formaldehyde also yields polymeric products and under certain conditions, the predominant product is 4,4 -methylenedianiline [101 -77-9] (26), an important intermediate for 4,4 -methylenebis(phenyhsocyanate) [101-68-8], or MDI (see Amines, aromatic amines, l thylenedianiline). 

Aromatic primary amines are not only binucleophiles at the amino group, but they also exhibit the properties of C,N-binucleophiles. Their reactions with internal perfluoroolefins lead to quinoline derivatives (98JFC(88)169, 94JCS(CC)134, 98T4949). Thus the reaction of aniline with 2//-heptafluorobut-2-ene yields phenyl(2-trifluoromethylquinolin-4-yl) amine (00ZOR109) when the reaction is carried out with the tetrafluoro-ethylene trimer, it leads to 2-trifluoromethyl-3-(l-N-phenylimino-2,2,2-trifluoroethyl)-4-(N-phenylamino)quinoline (98JFC(88)169). 

Acetone Peroxides A42-R Trimeric Methyleheaniliae. See Anhydro-formaldehydeaniline A404-R Trim ethyl aniline. See Ami nohem imel lit ene A215-R... 

Trimeric Acetone Peroxide. See under Acetone Peroxides A42-R Trimeric Methyleneaniline. See Anhydro-formaldehyde aniline A404-R Trimethylaniline. See Aminohemimellitene A215-R... 

The first stage in the production of MDI (9d) is condensation between aniline and formaldehyde, in the presence of HC1, under subatmospheric pressure, at 70-105 °C. This affords 4,4, 2,4 and 2,2 isomers of diaminodiphenylmethane (9a, 9b and 9c). Reaction with phosgene in an inert solvent, such as chlorobenzene, first at low temperature, and then heating to 120 °C, gives, for the 4,4 isomer (9a), MDI, trimers, tetramers and higher oligomers, the latter known as poly-MDI or PMDI. Continuous liquid-phase phosgenation is favored. 

The finding reported in these papers36,37 is in fact inconsistent with the results of previously mentioned electrochemical studies, the authors of which have found that at least both the head-to-tail and tail-to-tail dimers are formed under very similar experimental conditions. Furthermore, the observation of only the reduced dimer (and, similarly, trimer) is rather intriguing, as it has been demonstrated many times that the dimers, being the products of the initial stages of aniline oxidation, are easier to oxidize than the parent compound. 

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