Methods of making antidegradant compounds are disclosed in which a p-phenylenediamine is reacted with a diol to obtain mixtures comprising the antidegradant compounds.

A compound represented by the formula:

##STR00001## wherein R is selected from the group consisting of (i) substituted or unsubstituted alkyl with C=0 to 12 inclusive; (ii) substituted or unsubstituted aryl; and (iii) substituted and unsubstituted alkylaryl; wherein X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are each selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen; wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are each selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen and R.sup.2 and R.sup.3 may optionally be bridged by a polymethylene group; wherein when C=0 in R, the combined group R.sup.1 R.sup.2 is the same as the combined group R.sup.3 R.sup.4; and wherein when C=1 in R, each of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are hydrogen.

The invention provides an oil of lubricating viscosity, a dispersant and an amine-functionalized additive, wherein the amine-functionalized additive is derived from an amine having at least 3 or 4 aromatic groups. The invention further relates to the use of the lubricating composition in an internal combustion engine.

A grease composition includes: (A) a trimellitic acid ester, (B1) a phenyl naphthylamine, (B2) an alkyl diphenylamine, (C1) a succinic acid half ester, (C2) a sorbitan monoester, and (D) a urea-based thickener. This grease composition is excellent in anti-flaking, rust prevention, and oxidation resistance properties, and furthermore, a fatigue life of a rolling device and the like in which the grease is enclosed can be maintained for a long time.

Lubricating oil composition is provided. The composition includes several components including a major amount of a base oil, a mixture of alkylated diphenylamines having a weight ratio of mono-alkylated diphenylamine to di-alkylated diphenylamine ranging from 0.6 to 4.0, and a molybdenum or sulfur additive that provides synergistic enhancement of oxidation stability in combination with the mixture of alkylated diphenylamines.