Diaryl-p-phenylenediamines

Akrochem Antiozonant MPD-100. See M ixed diaryl-p-phenylenediamine Akrochem Antiozonant NIBud. See Nickel dibutyidithiocarbamate Akrochem Antiozonant PD-2. See N-(1,3-Dimethylbutyl)-N -phenyl-p-phenylenediamine Akrochem Calcium Stearate. See Calcium stearate... 

Diarylide orange. See Pigment orange 34 Diarylide yellow. See Pigment yellow 14 Diarylide yellow AAA. See Diarylanilide yellow N,N -Diaryl-p-phenylenediamine. See Mixed diaryl-p-phenylenediamine Diasmol. See 1,3-Nonanediol acetate, mixed esters DidstdS0... 

Mixed cresols (INCI). See Cresylic acid Mixed decanoic and octanoic acids, methyl esters. See Methyl caprylate/caprate Mixed diaryl-p-phenylenediamine CAS 68478-45-5 69853-84-4 Synonyms N,N -Diaryl-p-phenylenediamine Definition Mixed prod, contg. N,N -ditolyl-p-phenylenediamine, N, N -diphenyl-p-phenylenediamine, and N-phenyl-N -tolyl-p-phenylenediamine Empihcai C20H20N2... 

Novatone. See Acetanisole Novawet G-3300. See Isopropylamine dodecylbenzenesulfonate Novazone AS. See Mixed diaryl-p-phenylenediamine Novei a 10-3. See Deceth-3 Novel II1214GC-2. See Laureth-2 Novel il 1412-7. See Laureth-7 Novel N3.0-1216CO. See C12-16 pareth-3 Novelose 240, Novelose 260. See Starch Novelose 330. See Maltodextrin Noveon AA-1. See Polycarbophil Noveon CA-1, Noveon CA-2. See Calcium polycarbophil Novocaine. See Procaine Novodur L3FR, Novodur M3FR, Novodur ... 

See Sodium metaphosphate Optiwhite MX] Optiwhite P, Optiwhite . See Aluminum silicate Opus . See Epoxiconazole OPX. See Potassium 3-[(ethoxy-thioxomethyl) thio]-1 -propanesulfonate OR 5050. See Mixed diaryl-p-phenylenediamine Oramide DL 200 AF. See Cocamide DEA Oramide ML 115. See Cocamide MEA Oramide MLM 02. See PEG-3 cocamide Oramide MLM 06. See PEG-7 cocamide Oramide MLM 10. See PEG-11 cocamide Oramix BG 14. See Butyl glucoside Oramix CG 110-60. See Caprylyl/capryl glucoside... 

Methyl tallowate Microcrystalline wax Mineral oil Mixed diaryl-p-phenylenediamine Montan wax... 

Methylenebis 6-(1-methylcyclohexyl)-p-cresol 2,2 -Methylenebis (4-methyl-6-cyclohexylphenol) 4- and 5-Methylmercaptobenzimidazole Mixed diaryl-p-phenylenediamine P-Naphthol Nickel dimethyidithiocarbamate Nonylphenol Paraldehyde Pentaerythrityl tetrakis f3-(3, 5 -di-t-butyl-4-hydroxyphenyl) propionate] Pentaerythrityl tetrakis (p-laurylthiopropionate)... 

N,N -Di-p-naphthyl-p-phenylenediamine p,p -Dioctyldiphenylamine 6-Ethoxy-1,2-dihydro-2,2,4-trimethylquinoline Microcrystalline wax Mixed diaryl-p-phenylenediamine Paraffin N-Phenyl-N -(1-methylheptyl)-p-phenylenediamine... 

Mixed diaryl-p-phenylenediamine Vanox 2-AZ Wingstay 100AZ... 

Ditolyl-p-phenylenediamine Mixed diaryl-p-phenylenediamine C2oH2iCIN ... 

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... 

The ozonation mechanism for the iV-iV -diaryl-p-phenylenediamine antiozonants is identical to the above described mechanism except that the reaction terminates with the formation of the nitrone and the release of oxygen after reacting with the ozone, Step (3) [4]. 

Additionally, carbon radicals exhibit a high degree of energy, and few materials can effectively trap these intermediates. Diaryl-p-phenylenediamines such as N, A -diphenyl-p-phenylenediamine (Naugard J) and mixed diaryl-p-phenylenediamine (Novazone AS) are two examples of carbon radical traps. 

Dialkyl or diaryl group substituents hold the molecule more rigidly out of the plane of the benzene ring than corresponding monosubstituted amine groups. The free radicals produced from unsymmetrical p-phenylenediamine derivatives should react more slowly with ozone than those formed from analogous symmetrical compounds. 

The success of the diaUtyl-p-phenylenediamines led to the development of related antiozonants, i.e., aUtyl/aryl-analogs, N-isopropyl-N -pheny-p-phenylenediamine (IPPD) and N-cyclohexyl-N -phenyl-p-phenylenediamine, and mixed N,N -diaryl-p-phenylenedi-amine mixtures. 

The longer-chain alkyl substituents served to reduce the volatility. However, the fugitive nature of the protection offered by the di-octyl-p-phenylenediamine was attributed to the fact that it reacts directly with oxygen (O2) as well as ozone. Alkyl/aryl- or diaryl-/>-phenylenediamines are less subject to depletion by reaction with oxygen and are longer-lasting in rubber compounds. 

The antiozonants, N-(l,3-di-methylbutyl)-N -phenyl-p-phenylenediamine (6PPD) and the C7 and C5 alkyl-analogs were later introduced. In addition to their nse as antiozonants, p-phenylenediamines, primarily the more persistent mixed diaryl-derivatives, have replaced N-phenyl- 3-naphthylamine as antioxidants flex crack inhibitors and synthetic polymer antioxidant stabilizers. 

Antiozonant activity changes with time. For short periods of aging time, the dialkyl-p-phenylenediamines are the most effective antiozonants, very closely followed by the alkyl/ aryl analogs, with the diaryl being less effective. However, with increased aging time, the order of effectiveness is completely reversed, as oxidation and reaction with ozone occur—another reason for using mixtures of antiozonants, i.e, to provide protection for an extended period of aging. 

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