Octylated diphenylamine antioxidant

Aniline hydrochloride is directly used to produce diphenylamine, a very important feedstock in the production of 6PPD antiozonant, octylated diphenylamine antioxidant, and ADPA AO, all produced for rubber use. 

Diisobutylene reacts with diphenylamine to produce octylated diphenylamine antioxidant for rubber. 

NBR antioxidant pLASTOTffiRS, SYNTTiETIC - NITRILE RUBBER] (Vol 8) Octylated diphenylamines [101-67-7]... 

Because nitrile rubber is an unsaturated copolymer it is sensitive to oxidative attack and addition of an antioxidant is necessary. The most common practice is to add an emulsion or dispersion of antioxidant or stabilizer to the latex before coagulation. This is sometimes done batchwise to the latex in the blend tank, and sometimes is added continuously to the latex as it is pumped toward further processing. PhenoHc, amine, and organic phosphite materials are used. Examples are di-Z fZ-butylcatechol, octylated diphenylamine, and tris(nonylphenyl) phosphite [26523-78-4]. All are meant to protect the product from oxidation during drying at elevated temperature and during storage until final use. Most mbber processors add additional antioxidant to their compounds when the NBR is mixed with fillers and curatives in order to extend the life of the final mbber part. 

In an acetone extract from a neoprene/SBR hose compound, Lattimer et al. [92] distinguished dioctylph-thalate (m/z 390), di(r-octyl)diphenylamine (m/z 393), 1,3,5-tris(3,5-di-f-butyl-4-hydroxybenzyl)-isocyanurate m/z 783), hydrocarbon oil and a paraffin wax (numerous molecular ions in the m/z range of 200-500) by means of FD-MS. Since cross-linked rubbers are insoluble, more complex extraction procedures must be carried out (Chapter 2). The method of Dinsmore and Smith [257], or a modification thereof, is normally used. Mass spectrometry (and other analytical techniques) is then used to characterise the various rubber fractions. The mass-spectral identification of numerous antioxidants (hindered phenols and aromatic amines, e.g. phenyl-/ -naphthyl-amine, 6-dodecyl-2,2,4-trimethyl-l,2-dihydroquinoline, butylated bisphenol-A, HPPD, poly-TMDQ, di-(t-octyl)diphenylamine) in rubber extracts by means of direct probe EI-MS with programmed heating, has been reported [252]. The main problem reported consisted of the numerous ions arising from hydrocarbon oil in the recipe. In older work, mass spectrometry has been used to qualitatively identify volatile AOs in sheet samples of SBR and rubber-type vulcanisates after extraction of the polymer with acetone [51,246]. 

Over half of the remaining market for products used in the processing of rubber is made up of antioxidants, antiozonants and stabilizers, either amino compounds or phenols. Aniline is used to manufacture vulcanization accelerators, antioxidants and antidegradants. Of the latter, several are A-substituted derivatives of p-phenylenediamine and octyl dipheny-lamine. Diphenylamines terminate free-radical reactions by donating the amino hydrogen, and are used to protect a wide range of polymers and elastomers. Many synthetic rubbers incorporate alkylated diphenylamine antioxidants. Other antioxidants include aryl amine resinous products from, e.g. condensation of aniline and acetone in the presence of... 

Raw NBR containing 1.5% of the built-in antioxidant retained 92% of its original resistance to oxidation after exhaustive extraction with methanol. NBR containing a conventional aroma tic amine antioxidant (octylated diphenylamine) retained only 4% of its original oxidative stability after similar extraction. 

AI3-17279 Benzenamine, 4-octyl-N-(4-octylphenyl)- Bis(4-octylphenyljamine Bis(p-octylphenyl)amine CCRIS 6029 Di-n-octyl diphenylamine p,p-Dioctyl-diphenylamine Diphenylamine, 4,4 -dioctyl- EINECS 202-965-5 HSDB 5341 Naugalube 438 NSC 79268. Antioxidant in automatic transmission fluids, turbine oil, and synthetic lubricants used in jet turbine engines thermal stabilizer for automatic transmission fluid at high temperatures. Crystals mp= 96-97° insoluble in H2O (<1 mg/ml) LD50 (rat orl) = 7.58 g/kg. Uniroyal. 

The antioxidant used in thermoplastic polyurethane elastomers are hindered phenols, e.g., BHT, octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate, and pentaerythrityl-tetrakis-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate, and aromatic amines, e.g., 4,4 -di-tcrt-octyl-diphenylamine, as well as their combinations. Aromatic amines can, however, be employed only in very limited concentrations (250-550 ppm at most) because of their discoloring properties. 

Dioctyloxostannane. See Dioctyltin oxide Dioctylperoxydicarbonate. See Di (2-ethylhexyl) peroxydicarbonate 4,4 -Dioctylphenylamine. See p,p -Dioctyldiphenylamine 4,4 -Di-t-octylphenylamine Synonyms Diphenylamine, octylated Octylated diphenylamine ODPA Empirical C28H43N Properties M.w. 393.66 Uses Antioxidant for plastics, rubber, and lubricants... 

Octylamine N-Octylamine. See 1-Octanamine Octylated diphenylamine. See 4,4 -Di-t-octylphenylamine p,p -Dioctyldiphenylamine Octylated N-phenyl-a-naphthylamines CAS 68259-36-9 Empirical C24H29N Uses Antioxidant for lubricants... 

Figure 5.12 Separation of amine antioxidants and antiozonants by one-dimensional thin-layer chromatography. Solvent benzene - acetone - concentrated ammonium hydroxide (100 5 0.1) development distance 15 cm indicator 4% benzoyl peroxide in benzene. 1 = N-phenyl-l-naphthylamine 2 = N-phenyl-2-naphthylamine 3 = p-(p-tolylsulfonylamido)-diphenylamine 4 = nonylated diphenylamines 5 = octylated diphenylamines 6 = octylated diphenylamines 7 = octylated diphenylamines 8 = 4,4-dimethoxydiphenylamine 9 = 4-isopropoxydiphenylamine 10 = 4"-isopropyl-aminodiphenylamine 11 = N, N-diisopropyl-p-phenylenediamine 12 = N,N -6i-sec-h xtyi-p-p)Lieny emdizTmne. Reproduced from [119]...

Antioxidants stabilize the polyether against oxidative attack during manufacture and storage in addition, they reduce the danger of core discoloration or self-ignition during foam manufacture. Most commonly, 2,6-di-tert-butyl-p-cresol and 4,4 -di-tert-octyl-diphenylamine are used for this purpose [513]. 

Slightly staining antioxidants, which are derivatives of diphenylamine, such as octylated diphenylamine (ODPA), styrenated diphenylamine (SDPA), or 4,4-bis (dimethylbenzyl)-diphenylamine are especially effective in CR compounds. 

General purpose antioxidants commonly used are octylated diphenylamine types, alkylated-arylated bisphenolic phosphate (also inhibits gel formation in the polymer), polymerized l,2-dihydro-2,2,4 trimethylquinoline (AgeRite Resin D or Flectol TMQ). This is by no means a complete list as many other types are equally as... 

Having no reactive double bonds EVM elastomers have an inherently excellent heat resistance. But for an optimum stability it is necessary to add approximately 1 phr of an antioxidant. Here it is necessary to select the right substance, because many well-known antioxidants cannot be used in peroxide cure. For an optimum heat resistance, the addition of 1 phr of styrenated or octylated diphenylamine (SDPA or OOP A) is recommended. Aralkylated phenols can be used as nonstaining antioxidants. To protect the vulcanizates from hydrolysis at elevated temperatures and higher humidity, the addition of a polycarbodiimide may be necessary. 

Examples of alkoxy and peroxy radical trap antioxidants are hindered amines (i.e., octylated diphenylamine, Octamine) and phenols (i.e., butylated hydroxytoluene, Naugard BHT). 

The selection of an antioxidant is very important, the preferred one being octylated diphenylamine which may be used up to a level of 6phr. 

Polychloroprene vulcanisates have excellent resistance to flex cracking. However, for products that will be flexed severely in service, compounds should be soft, with low modulus and high elongation wherever possible. This should be done using well dispersed loadings of soft carbon blacks (MT or SRF) rather than mineral fillers, although up to 20 phr precipitated silica will be beneficial. A good antioxidant/antiozonant protection system such as 2 phr octylated diphenylamine and 1 phr mixed diaryl /7-phenylene diamine is required. The plasticiser should be kept to a minimum and preferably be an aromatic oil esters should be avoided. 

Bisphenol A, polybutylated 4,4 -Butylidenebis (6-t-butyl-m-cresol) Butyraldehyde-aniline condensation product N,N -Di (n-octyl)-p-phenylenediamine Diphenylamine-acetone Zinc diisobutyidithiocarbamate Zinc 2-mercaptotoluimidazole antioxidant, NR latex Dimethylamine antioxidant, NR, SR... 

However, the experimental investigations conducted have shown that the premises cited above actually are not justified. In [33] it was shown that the antioxidants usually are not consumed according to a linear law. Thus, 2,6-di-tert-octyl-4-methylphenol, when introduced into polypropylene, is consumed first rapidly, then more slowly, and then again more rapidly. The antioxidant di-tert-butyl-p-cresylmethane in polypropylene is consumed according to a first order law until its concentration is reduced to the critical value, after which it disappears rapidly. If polypropylene is stabilized by phenyl-a-naphthylamine, then the latter is consumed first slowly, and then considerably more rapidly during oxidation. The curves of the consumption of the antioxidants mentioned are depicted in Fig. 16. Anal-logous results have been obtained in other works in which the kinetics of the consumption of diphenylamine in the inhibition of the oxidation of polypropylene, cetane, and other hydrocarbons was investigated. 

Isobutylene reacts with ammonia to make f-butylamine, an important feedstock in the synthesis of TBBS rubber accelerator, one of the two most widely used accelerators. Isobutylene is dimerized to make diisobutylene, which is used to produce octy-lated diphenylamine (a commonly used rubber antioxidant) and para-t-octyl phenol (a feedstock for the most common phenolic tackifier resin used by the rubber industry). 

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