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  Compound and method of making the compoundUSPTO Application #: 20080090742Title: Compound and method of making the compound Abstract: The present application is directed to compounds that are the reaction product of (i) a polyacrylate, (ii) a hindered phenol, (iii) a diaryldiamine and optionally (iv) an alkyl amine. Methods for making these compounds and formulations employing the compounds are also disclosed. (end of abstract) Agent: Mh2 Technology Law Group (cust. No. W/newmarket) - Tysons Corner, VA, US Inventor: Naresh C. Mathur USPTO Applicaton #: 20080090742 - Class: 508454 (USPTO) The Patent Description & Claims data below is from USPTO Patent Application 20080090742. Brief Patent Description - Full Patent Description - Patent Application Claims
FIELD OF THE DISCLOSURE [0001]The present application is directed to novel compounds, processes for making the compounds, and compositions that comprise the compounds. BACKGROUND OF THE DISCLOSURE [0002]Lubricating oils as used in the internal combustion engines and transmissions of automobiles or trucks are subjected to a demanding environment during use. This environment results in the oil suffering oxidation which is catalyzed by the presence of impurities in the oil, such as iron compounds, and is also promoted by the elevated temperatures of the oil during use. [0003]The oxidation of lubricating oils during use is often controlled to some extent by the use of antioxidant additives. Antioxidant additives can extend the useful life of the lubricating oil by, for example, reducing or preventing unacceptable viscosity increases. [0004]A combination of antioxidants are often employed in lubricants. One such combination includes both hindered phenol compounds and alkylated diphenylamines as antioxidants. These antioxidants are believed to work synergistically by converting relatively reactive alkoxy and/or alkyl radicals to less reactive phenoxy radicals. SUMMARY OF THE DISCLOSURE [0005]In accordance with the disclosure, one aspect of the present application is directed to a compound that is the reaction product of (i) a polyacrylate, (ii) a hindered phenol, (iii) a diaryldiamine and optionally (iv) an alkyl amine. [0006]Another aspect of the present application is directed to a compound of formula V [0007]where Y is a group having a formula VI, [0007] [0008]R.sup.1 is an aliphatic or aromatic group, [0009]R.sup.2 is hydrogen or methyl, [0010]R.sup.3 and R.sup.4 are independently chosen from hydrogen or a linear or branched C.sub.1 to C.sub.12 alkyl group, with the proviso that at least one of R.sup.3 and R.sup.4 is a branched C.sub.3 to C.sub.12 alkyl group, [0011]R.sup.5 is a secondary amine substituent, [0012]R.sup.6 and R.sup.7 are independently chosen from saturated or olefinically unsaturated aliphatic alkyl groups, and [0013]Ar and Ar' are groups independently chosen from substituted or unsubtituted aryl groups having from 6 to 50 carbon atoms. [0014]Another aspect of the present application is directed to a process for forming a first compound, the process comprising combining (i) a polyacrylate, (ii) a hindered phenol, (iii) a diaryldiamine and optionally (iv) an alkyl amine. [0015]Another aspect of the present application is directed to a lubricant composition. The composition comprises a base oil; and a first compound that is the reaction product of (i) a polyacrylate, (ii) a hindered phenol, (iii) a diaryldiamine and optionally (iv) an alkyl amine. [0016]Another aspect of the present application is directed to an additive package. The additive package comprises a diluent; and a first compound that is the reaction product of (i) a polyacrylate, (ii) a hindered phenol, (iii) a diaryldiamine and optionally (iv) an alkyl amine. [0017]Another aspect of the present application is directed to a method for reducing the oxidation of a lubricating oil. The method comprising placing in the crankcase of an internal combustion engine a lubricating composition of the present application. [0018]Additional aspects and advantages of the disclosure will be set forth in part in the description which follows, and can be learned by practice of the disclosure. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the disclosure, as claimed. DESCRIPTION OF THE EMBODIMENTS [0019]The present application is directed to compounds prepared by reacting (i) a polyacrylate, (ii) a hindered phenol, (iii) a diaryldiamine and optionally (iv) an alkyl amine. In some aspects of the present application, the resulting compounds comprise both a hindered phenol functional group and a diaryldiamine functional group. The plurality of functional groups of the compounds of the present application may result in useful properties, such as, for example, compounds having good antioxidant function and/or other capabilities, as described in more detail below. [0020]Representative examples of suitable polyacrylates used to form the compounds of the present application include, but are not limited to, compounds of the formula I, wherein R.sup.1 is an aliphatic group or aromatic group, R.sup.2 is hydrogen or methyl and q is an integer from about 2 to about 4. Non-limiting examples of a polyacrylate suitable for use herein include trimethylolpropane triacrylate (TMPTA), hydroquinone diacrylate, hydroquinone dimethacrylate, pyrogallol diacrylate, pyrogallol dimethacrylate, pyrogallol triacrylate, resorcinol diacrylate, resorcinol dimethacrylate, glycol diacrylate, glycol dimethacrylate, glycerol diacrylate, glycerol trimethacrylate, 1,1,1-trimethylol ethane triacrylate, glucose polyacrylate, pentaerythritol tetraacrylate, pentaerythritol trimethacrylate, diethyleneglycol diacrylate, triethyleneglycol dimethacrylate, propyleneglycol diacrylate and the like. [0021]Suitable hindered phenols for use in the present application include compounds of formula II, wherein R.sup.3 and R.sup.4 can be independently chosen from, for example, hydrogen or a linear or branched C.sub.1 to C.sub.12 alkyl group, with the proviso that at least one of R.sup.3 and R.sup.4 is a branched C.sub.3 to C.sub.12 alkyl group. Non-limiting examples of suitable phenols include compounds chosen from 2-tert-butylphenol; 2,6-ditert-butylphenol; 2-isopropylphenol; 2,6-diisopropylphenol; 2-sec-butylphenol; 2,6 di-sec-butylphenol; 2-tert-hexylphenol; 2,6-ditert-hexylphenol; 2-tert-butyl-o-cresol; 2-tert-dodecylphenol; 2-tert-decyl-o-cresol and 2-tert-butyl-6-isopropylphenol. In one embodiment, the hindered phenol is 2,6 di-tert-butylphenol. [0022]Suitable diaryldiamines for use in forming the compounds of the present application include reactant compounds of the formula III, wherein Ar and Ar' each independently represent a substituted or unsubtituted aryl group having from about 6 to about 50 carbon atoms; and wherein R.sup.5 is an amine substituent. Non-limiting examples of suitable amines include primary amine substituents such as --NH.sub.2, --[NH(CH.sub.2).sub.n].sub.mNH.sub.2, --(CH.sub.2).sub.nNH.sub.2, and --CH.sub.2-aryl-NH.sub.2 in which n is an integer ranging from about 1 to about 20, such as from about 1 to about 10, or in another embodiment, from about 2 to about 4; and m is an integer having a value of from about 1 to about 20, such as from about 2 to about 10. Non-limiting examples of other substituents that can also be bonded to Ar and Ar' in addition to the R.sup.5 substituent include one or more additional primary amine substituents, such as those listed above for R.sup.5; aliphatic hydrocarbon groups, such as alkyl groups having from about 1 to about 20 carbon atoms; hydroxyl; carboxyl and nitro groups. In some embodiments, both Ar and Ar' can be phenyl groups. For example, the diaryldiamine can be an N-phenylphenylenediamine (NPPDA), such as N-phenyl-1,3-phenylenediamine, N-phenyl-1,2-phenylenediamine and N-phenyl-1,4-phenylenediamine. Continue reading... Full patent description for Compound and method of making the compound Brief Patent Description - Full Patent Description - Patent Application Claims Click on the above for other options relating to this Compound and method of making the compound patent application. ###  How KEYWORD MONITOR works... a FREE service from FreshPatents1. Sign up (takes 30 seconds). 2. Fill in the keywords to be monitored. 3. Each week you receive an email with patent applications related to your keywords. Start now! - Receive info on patent apps like Compound and method of making the compound or other areas of interest. ### Previous Patent Application: Lubricating oils with enhanced piston deposit control capability Next Patent Application: Compounds and methods of making the compounds Industry Class: Solid anti-friction devices, materials therefor, lubricant or separant compositions for moving solid surfaces, and miscellaneous mineral oil compositions ### FreshPatents.com Support Thank you for viewing the Compound and method of making the compound patent info. IP-related news and info Results in 0.26289 seconds Other interesting Feshpatents.com categories: Accenture , Agouron Pharmaceuticals , Amgen , AT&T , Bausch & Lomb , Callaway Golf |
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