1. AMINE AND PHENOL-BEARING COMPOUNDS
Given the high popularity and effectiveness of amine and phenol derivatives as lubricant anti oxidants, the combination of amine and phenolic moieties in one molecule represents a logic approach to enhance performance. In a prior art, fusing amine with a long carbon chain 3,5- di-tert-butyl-4-hydroxyphenalkyl group that separates the phenol group from the amino nitrogen leads to novel products with lower volatility, better thermal stability, and higher solubility in oils.
Nelson and Rudnick reacted an ethyoxylated alkyl phenol with an alkyl arylamine in the presence of an aldehyde. The resulting product had improved antioxidant potency owing to a syn ergistic action between the phenolic moiety and the amine, and also showed enhanced solubility in oils owing to the presence of alkylated aromatic moiety in the molecule. Phenolic imidazo lines have been prepared from polyaminophenols and carbonyl compounds.
In addition to providing antioxidant activity, the products also have corrosion inhibition and metal deactivation properties owing to the cyclic imidazoline moiety. Multifunctional additives containing sulfur, nitrogen, and phenolic moieties in one molecule have been reported. In this instance, mercaptobenzothiazoles or thiadiazoles are Mannich reacted with HP antioxidants to yield oil-soluble compounds with antioxidant and antiwear properties. More complex product having similar functionalities was obtained by reacting a sulfur-containing HP ester with an ADPA.
2. MULTIFUNCTIONAL AMINE AND PHENOL DERIVATIVES
The industry-wide trend in the reduction of phosphorus and sulfur, in particular, ZDDP in fnished lubricants has led to increasing activities in the development of novel multifunctional additives that have combined properties of antioxidancy, antiwear, and to some extent dispersancy, while having low-to no-sulfur and phosphorus contents. It has been shown that products obtained from reacting alkyl or alkenyl succinic acid anhydride with an appropriate amine may impart such multifunctionalities. Product made by reacting a polyalkenylsuccinic acid or anhydride frst with an aromatic secondary amine, then with an alkanol amine, was found to provide appreciable antioxidancy, dispersancy, and anticorrosion effects to engine oils as tested in a Caterpillar engine test.
A more recent U.S. Patent literature discloses materials made from the reaction of alkyl or alkenyl succinic acid derivative with a diamino naphthyl compound for use as antioxidant, antiwear, and soot dispersing agents for lubricating oils. By fusing a HP moiety to an alkenyl succinimide domain, a novel dispersant having antioxidant property was obtained. The product improved the performance of engine oils in the sequence VG, an industry recognized sludge test to evaluate the ability of a lubricant in preventing the formation of sludge and varnish deposits in a fred engine. U.S. Patent 5,075,383 describes novel antioxidant–dispersant additives obtained by reacting amino-aromatic polyamine compound, including aromatic secondary amines, with ethylene–propylene copolymer grafted with maleic anhydride. Engine oils containing the additives displayed improved performance characteristics in laboratory oxidation and sludge dispersancy tests, as well as in the sequence VE and the MWM-B engine tests.
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