Phenyl-jS-naphthylamine

Solely epidermal lesions were pointed out by Sato (1961) in guinea pigs sensitized with phenyl-jS-naphthylamine. 

A large number of antioxidants of organic structure, of the type of amines and phenols, were investigated in [42, 43]. The additives were introduced by powdering the capron in the form of crumbs before spinning of the fiber, as well as into the fused caprolactam before polymerization. The antioxidants beloi ing to the amine class, such as N,N -di-/3 -naphthyl-p-phenylenediamine, N, N-phenylcyclohexyl-p-phenylenedi-amine, N,N -diphenyl-p-phenylenediamine, and phenyl-jS-naphthylamine, preserve the strength of the fiber by 70-95% when it is heated for 2 hr... 

Under the influence of small additions of amines, phenols, and certain other classes of compounds, the process of polymer oxidation is sharply decelerated for example, 1% phenyl-jS-naphthylamine reduces the rate of oxidation of polybutadiene during the steady-state period at 70°C more than six-fold, while the duration of this period increases sharply. By decelerating the oxidation process, the inhibitor naturally reduces the rate and even changes the character of the structural changes in the polymers. 

In the case of diphenylamine the minimum is displaced toward higher concentrations in comparison with phenyl-jS-naphthylamine. The curve of di-/3, -naphthylamine does not pass through a minimum, but approaches a constant value. The cause of this is the low activity of the dinaphthylnitrogen radical, which is incapable of initiating oxidation of the rubber. 

In reaction (4) the material AH actually acts as a pro-oxidant. If reaction (5a) is more likely than reaction (2b) and the reaction rate of (5b) is low, AH can function as an oxidation retarder. By terminating chain reactions as in (6a) and (6b) the material acts as a chainbreaking antioxidant. A single antioxidant may act in all of these ways more or less simultaneously so that whilst in some circumstances the material may appear primarily as an antioxidant in other circumstances it may show pro-oxidant tendencies. Shelton and Cox (1954) found that when phenyl-jS-naphthylamine (PBN) was used in natural rubber above a critical concentration the oxidation rate increased (Fig. 9.1.). The most important chain-breaking antioxidants are amines and phenols (see Section 9.5). 

Shlyapnikov et al. [929] have reported distillation in vacuo at different temperatures (from 20° to 200°C), with indications of the degree of extraction from 0.02-0.1 g PE for 0.2-2.0% diphenylamine, phenyl-a-naphthylamine (Neozon A), phenyl-jS-naphthylamine (Neozon D), A-phenyl-A -cyclo-hexyl-p-phenylenediamine, A,A -di-/3-naphthyl-p-phenylenediamine, lonol, 2,4,6-tri-f-butylphenol, propyl gallate, a-naphthene, 2,2 -methylenebis(4-methyl-6-f-butylphenol), 2,2 -thiobis(4-methyl-6-f-butylphenol), 2,2 -methylenebis(4-chloro-6-f-butyl-phenol), 2,6-bis(2-hydroxy-3-f-butyl-5 -methylben-zyl)-4-methylphenol, and Tinuvin 326 reported accuracy of 1-2% using derivative (n = 2) UV spectrophotometry. 

Aiylnaphthalenes. Arylnaphthalenes can be prepared by replacement of the amino group of naphthylamines by aryl groups. a-Phenyl-naphthalene can be prepared satisfactorily only through the stabilized diazonium salt method, but jS-phenylnaphthalene is obtained readily by several procedures. A considerable number of derivatives of 8-phenyl-naphthalene have been prepared. An example is 5-nitro-6-methoxy-2-phenylnaphthalene (XII), which can be obtained in 19% yield Irom the nitromethoxy-jS-naphthylamine and benzene. From the reaction between diazotized 8-naphthylamine and nitrobenzene and sodium acetate, j3-(2-nitrophenyl)-naphthalene (XIII 14%) and j3-(4-nitrophenyl)-naphthalene (XIV 26%) are formed. 

In addition to resedine, resedinine, phenyl-/3-naphthylamine, and jS-hydroxy-phenylethylamine, the above-ground parts of this plant contain two new alkaloids, lutine (49) and lutinine (50). ... 

The arsinic acid, (NH2CeH4)2As02H, is also formed to a small extent 39). Literature up to 1944 is well covered in an article 14) which describes the arsonation of phenols, phenyl ethers, phenylamines, a-naphthylamines (but not jS-), and dibenzofuran. A pyridine derivative, 2-pyridinol, can also be arsonated in the 3- or 5-position by this method 40). 

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