Phenyl-/?-naphthylamine

Smoked sheet, 40 lamp black, 1 phenyl-/ -naphthylamine, 3.5 dicumyl peroxide 50 min at 140° C Methyl methacrylate 52 — 96 96... 

Problem 19.29 Use the Bucherer reaction to prepare 2-(N-methyl)- and 2-(N-phenyl)naphthylamines. CHjNHj and C HjNH replace NH,. 

Aromatic amines, such as phenyl- -naphthylamine or condensation products of diphenylamine with acetone condensates, are excellent antioxidants and antiozonants but cause color development. From the sterically hindered phenols, monocyclic phenols, such as 2,6-di-teit-butyl-p-cresol, are less effective antioxidants but remain white and nontoxic during aging. They are, however, volatile and provide poor protection at elevated processing temperatures. Polycyclic phenols, such as 2,2 -methylene-bis (4-methyl-6-teit-butylphenol), are relatively nonvolatile, but become discolored by oxidation to a conjugated system. O Shea... 

Polymerization. All experiments were run under a high vacuum system. Monomer was added from a breakseal to the catalyst solution. The polymerization was stopped by pouring the reaction mixture into excess methanol containing phenyl / -naphthylamine, and precipitated polymer was vacuum dried under room temperature. 

Amines have been used for the following purposes related to expls,propellants, pyrotechnic compositions and fuels a).Rtabilizers for NC propellants(eg, diphenylaminc, nitro-Jiphenylamine and phenyl-/ -naphthylamine, the last examined in France(Ref 3) b)Sensi-tizers for some expl and propellent compns (Ref 4 and addnl ref d) c)Smoke-producing compels (Addnl Ref d) d)Liquid fuels for rockets in conjunction with strong oxidizers, such as nitric acid(some of these are hyper-golic) (Refs 6 8 and addnl refs e,g,i,k l) e)Additives to gasoline and other motor fuels (Addnl refs a,b,c f)... 

Acetone-extracted pale crepe, 5 zinc oxide, 1 stearic acid, 1 phenyl- -naphthylamine, 0.7 Santocure, 2.5 sulfur 30 min at 140° C... 

For the last block, a styrene-in-cyclohexane solution is prepared and purged similar to the starting solution, and the proper amount is added by syringe directly into the polymerization bottle at 50°C. This portion of the polymerization is allowed to proceed for an additional 3 hours and is terminated by the addition of a few milliliters of methanol. The polymers are precipitated in methanol in a Waring Blendor, stabilized with 1% N-phenyl-/ -naphthylamine and dried in a vacuum oven. If the product is hydrogenated, the quench with methanol is not done and the cyclohexane solution of the polymer is used directly. 

Ethyl 754 3,5-di-terf-butyl-4-hydroxybenzyl alcohol PBNA N-phenyl- -naphthylamine... 

Sulfuric acid is also a very satisfactory catalyst aluminum alkoxides also are useful, especially when the alcohols would be adversely affected by strong acids. Sodium alkoxides produce undesirable side reactions and give lower yields. When alkahne catalysts are employed, an alkaline polymerization inhibitor, such as j >-phenylenediamine or phenyl- -naphthylamine, should be used instead of hydroquinone. 

Secondary diaryl amines phenyl naphthylamines, substituted diphenylamines, and para-phenylenediamines ... 

Parker and Barnes [90] found that in solvent extracts of rubbers, the strong absorption by pine-tar and other constituents masks the absorption spectra of phenyl naphthylamines. 

Staining (amines) phenyl naphthylamines. 4,4-dialkyl or dialkoxydiphenyl-amines. N,N-dialkyl or diaryl-p-phenylenediamines staining (phenols) styrenated phenols, substituted phenols, ct- or p-bridged substituted phenols... 

Practically all the secondary amines and derivatives of para-phenyl-enediamine used for the stabilization of raw and cured rubbers are suitable for the stabilization of polyolefins [26]. However, in this case we must consider that the amines color the polymer a blackish-brown color. Hence they can be used only in the preparation of technical objects, colored deep shades. The amines most widely used in the practice of stabilization of polyolefins are cited in Table 6, We should indicate that phenyl-/ -naphthylamine, phenylcyclohexyl-p-phenylenediamine, and N,N -di-/ -naphthyl-p-phenylenediamine are the most effective. 

Of the amines, esters of /3-aminocrotonic and p-aminobenzoic acids, p-aminobenzenesulfamide [63, 266], hexamethylenetetramine [267], and certain others have been used for the stabilization of polyvinyl chloride. Phenyl-/ -naphthylamine, ethylphenylethanolamine [269], dicyanallqtl-amines [270], caprolactam [271], and N-(p-aminophenyl)hexamethylene-imine [268] have been recommended in the patent literature for the stabilization of polyvinyl chloride and vinyl chloride copolymers,... 

Chemical relaxation of stress in rubbers of the first type proceeds at a lower rate than that of rubber of the second type. In both types of rubbers, stress relaxation is determined by the breakdown of transverse bonds, formed during the process of vulcanization (Fig. 166). Moreover, the introduction not only of phenyl-/ -naphthylamine, but also of such substances as the condensation products of acetone and aniline, mercaptobenzimidazole, or the condensation product of diphenylamine and acetone into rubbers vulcanized only with sulfur and altax substantially reduces the rate of decomposition of transverse bonds (Fig. 167). 

ChIor.beiizol]-< 1 azo 1 -[N-(2.4-dinitro-phenyl).naphthylamin-(2)] 18 II195. 

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