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(12) Patent Application Publication (10) Pub. No.: US 2010/0152079 A1 Cherpeck Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2010/0152079 A1 Cherpeck Et Al US 20100152079A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2010/0152079 A1 Cherpeck et al. (43) Pub. Date: Jun. 17, 2010 (54) LUBRICATING OL COMPOSITIONS (22) Filed: Dec. 16, 2008 CONTAINING A TETRAALKYL-NAPTHALENE-18 DIAMINE Publication Classification ANTOXDANT (51) Int. Cl. CIOM 39/06 (2006.01) (75) Inventors: Richard E. Cherpeck, Cotati, CA CIOM. I.33/2 (2006.01) (US); Carrie Y. Chan, Daly City, CIOM 37/10 (2006.01) CA (US); Gaurav Bhalla, Hercules, CA (US) (52) U.S. Cl. .......................... 508/362; 508/556; 508/370 (57) ABSTRACT Correspondence Address: Disclosed is a lubricating oil composition containing an oil of CHEVRON CORPORATION lubricating viscosity and a N.N.N',N'-tetraalkyl-naphthalene P.O. BOX 6006 1,8-diamine and at least one additive selected from antioxi SAN RAMON, CA 94583-0806 (US) dants, dispersants, and detergents which together provide superior oxidation inhibition and are suitable lubricants for (73) Assignee: Chevron Oronite Company LLC automotive and truck crankcase lubricants; as well as trans mission lubricants, gear lubricants, hydraulic fluids, com (21) Appl. No.: 12/336,128 pressor oils, diesel and marine lubricants. US 2010/0152079 A1 Jun. 17, 2010 LUBRICATING OL COMPOSITIONS esters and Sulfurized ester-olefins and a secondary aliphatic CONTAINING A amine. U.S. Pat. No. 6,306,802 discloses of an antioxidant TETRAALKYL-NAPTHALENE-18 DIAMINE mixture containing a combination of an oil soluble molybde ANTIOXDANT num compound and an aromatic amine. 0005 Commonly, antioxidant compounds which were FIELD OF THE INVENTION intended to decompose hydroperoxides or peroxides (includ 0001. The present invention is directed in part to a lubri ing Sulfurized olefins, metal dithiocarbamates, dithio cating oil composition containing an oil of lubricating vis phospates, phosphites, thioesters, etc.) are increasingly diffi cosity, a N.N.N',N'-tetraalkyl-naphthalene-1,8-diamine and a cult to incorporate into the finished lubricant due to the lubricating oil additive. Particularly effective is a combina undesirable amounts of Sulfur, phosphorous and ash content tion of a N.N.N',N'-tetraalkyl-naphthalene-1,8-diamine and a they add to the lubricating oil composition. It is known that second antioxidant Such as diarylamine which together pro Sulfur, phosphorous and ash content may negatively impact vide superior oxidation inhibition. pollution control devices (such as poisoning catalysts, etc.) which are finding increasing application. Thus, there is a need BACKGROUND OF THE INVENTION for new antioxidants and antioxidant systems which do not 0002 Diarylamine antioxidants are known and have been negatively impact pollution control equipment yet provide widely used to improve the thermal-oxidative stability and/or improved antioxidancy performance to handle the typical light induced degradation in numerous products used in engi higher operating temperatures and longer service life desired. neering; for example, they can improve the performance Synergistic antioxidant systems are particularly important properties in lubricants, hydraulic fluids, metal working flu since they reduce the overall additive impact. For example, ids, fuels or polymers, just to name a few. Some antioxidants such as diphenylamines cannot be used at 0003 Commonly, these diarylamines have been alkylated, relatively high concentrations since this may result in sedi see for example, U.S. Pat. No. 2,943,112 which discloses an mentation or deposits in hot engine areas such as the diesel improved process for alkylating diphenylamine and U.S. Pat. ring areas in diesel engines. Thus, one aspect of the invention No. 3,655,559 which discloses alkylated diphenylamines as is directed to an improved antioxidant system comprising a stabilizers. Alkaryl substituted diphenylamines and phenyl free radical antioxidant and an effective peroxide decomposer napthylamines (such as C.-methylstyryl-diphenylamine) are selected from an tetraalkyl-naphthalene-1,8-diamine. disclosed for example in U.S. Pat. Nos. 3,533,992: 3,452,056 and 3,660,290. 0004 Synergist and antagonist combinations of antioxi SUMMARY OF THE INVENTION dants have been disclosed. Effective synergistic mixtures of antioxidants are typically compounds that intercept oxidation 0006. The present is directed in part to a lubricating oil by two different mechanisms. For example, those in which composition which provides improved oxidation stability. one compounds functions as decomposer of peroxides and Accordingly the compositions of the present invention have the other compound functions as an inhibitor of free radicals. various uses Such as lubricants for automotive and truck Well known heterosynergism has been disclosed between crankcase lubricants; as well as transmission lubricants, gear Sulfur and phosphorous containing compounds (such as Sul lubricants, hydraulic fluids, compressor oils, diesel and fides, dithiocarbamates, phosphites and dithiophosphates) marine lubricants. The lubricating oil compositions of the and aminic or phenolic antioxidants. U.S. Pat. No. 2,718,501 present invention comprise at least one oil of lubricating discloses a synergistic mixture of a Sulfur-containing com Viscosity, an oil soluble antioxidant according to formula I: pound. Such as a wax Sulfide or dioctadecyl disulfide, and an aromatic amine compound having at least 2 aromatic rings, Such as phenyl alpha-naphthyl amine, for use in preventing R. R3 oxidation in lubricating oils. For example, U.S. Pat. No. 2.958,663 discloses an extreme pressure lubricant composi tion containing from 0.01 to 5 percent each of sulfurized oleic acid, Cs-C alkenyl Succinic acid, chlorinated paraffin wax containing from 20 to 60 percent chlorine, diphenylamine and N,N-salicylal-1,2-propylenediamine. U.S. Pat. No. 3.345,292 discloses stabilized alkyl substituted diaryl sul fides for use as functional fluids where the stabilizer can be diaryl amine or alkylated phenol. U.S. Pat. No. 4,032,462 0007 wherein R. R. R. and Ra are each independently discloses lubricants having improved antioxidancy having an selected from alkyl groups each having from 1 to 20 carbon oil soluble antimony compound and an oil soluble antioxidant atoms, and at least one additive selected from antioxidants, selected from sterically hindered phenols and thiophenols, dispersants, and detergents. The antioxidant according to for and aromatic amines, and mixtures of these antioxidants. U.S. mula I is effective by itself when employed in a lubricating Pat. No. 4,089,792 discloses lubricants having a an antioxi composition. However, there is an improvement in antioxid dant mixture of a primary amine and an antioxidant selected ancy performance when the compounds of formula I are from aromatic or alkyl sulfides and polysulfides, sulfurized employed with a free radical antioxidant. Thus another aspect olefins, sulfurized carboxylic acid esters and sulfurized ester is directed to a lubricating oil composition comprising an oil olefins. U.S. Pat. No. 4,102.796 discloses lubricants having of lubricating viscosity and an antioxidant is a mixture com an antioxidant mixture of aromatic and alkyl sulfides and prising: a) from 0.1 to 10 weight percent of a first antioxidant polysulfides, sulfurized olefins, sulfurized carboxylic acid according to formula I: US 2010/0152079 A1 Jun. 17, 2010 thus one aspect is directed to the use of the compounds of formula I in a lubricating oil composition for oxidation retar R2 R3 dation purposes. RIn 7 DETAILED DESCRIPTION OF THE INVENTION 0014 Inhibition of free radical-mediated oxidation is one of the most important reactions in organic Substrates and is commonly used in rubbers, polymers and lubrication oils; namely, since these chemical products may undergo oxidative damage by the autoxidation process. Hydrocarbon oxidation 0008 wherein R. R. R. and Ra are each independently is a three step process which comprises: initiation, propaga selected from alkyl groups each having from 1 to 20 carbon tion and termination. Oxidative degradation and the reaction atoms; and mechanisms are dependent upon the specific hydrocarbons, 0009 b) from 0.01 to 10 weight percent of a second anti temperatures, operating conditions, catalysts such as metals, oxidant selected from the formula etc., which more detail can be found in Chapter 4 of Mortier R. M. et al., 1992, “Chemistry and Technology of Lubricants Initiation. VCH Publishers, Inc.; incorporated herein by ref H erence in its entirety. Initiation involves the reaction of oxy gen or nitrogen oxides (NO) on a hydrocarbon molecule. Ra-N-R Typically, initiation starts by the abstraction of hydrocarbon proton. This may result in the formation of hydrogen peroxide wherein R and Rare each independently aryl from 6 to 10 (HOOH) and radicals such as alkyl radicals (R.) and peroxy carbonatoms which may be unsubstituted or substituted with radicals (ROO.). During the propagation stage, hydroperoX one or two alkyl groups each having from 1 to 20 carbon ides may decompose, either on their own or in the presence of atOmS. catalysts such as metal ions, to alkoxy radicals (RO.) and peroxy radicals. These radicals can react with the hydrocar 0010 Improvement of the combination of component a) bons to form a variety of additional radicals and reactive and component b) is demonstrated at ratios of componenta) oxygen containing compounds such as alcohols, aldehydes, to component b) from about 0.5:1 to about 10:1 and even ketones and carboxylic acids; which again can further poly more particularly from about 0.75:1 to about 5.1. Due to the merize or continue chain propagation. Termination results demonstrated improvement in oxidative stability of the com from the self termination of radicals or by reacting with position afforded by the mixture of components a) & b), the oxidation inhibitors. mixture of these components present in the total composition 0015 The uncatalyzed oxidation of hydrocarbons attem is less than 5 weight percent. More preferably the mixture of peratures of up to about 120° C. primarily leads to alkyl a) & b) is from 0.5 to 2.0 weight percent based on the total hydroperoxides, dialkylperoxides, alcohols, ketones; as well weight of the composition.
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