Compounds and methods of making the compounds

Abstract

The present application is directed to compounds that are the reaction product of (i) a hydrocarbyl phenol, (ii) a hindered phenol; (iii) an diaryldiamine and (iv) an aldehyde. Methods of making and using the compounds of the present application are disclosed.

1 . A compound that is the reaction product of (i) a hydrocarbyl phenol, (ii) a hindered phenol, (iii) an diaryldiamine and (iv) an aldehyde. 
     
     
         2 . The compound of  claim 1 , wherein the hydrocarbyl phenol is a compound of the formula I, 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are independently chosen from hydrogen or hydrocarbyl groups, with the proviso that at least one of R 1  and R 2  is a hydrocarbyl group. 
       
     
     
         3 . The compound of  claim 1 , wherein the hindered phenol is a compound of the formula II, 
       
         
           
           
               
               
           
         
         wherein R 3  and R 4  are independently chosen from hydrogen and a linear or branched C 1  to C 12  alkyl group, with the proviso that at least one of R 3  and R 4  is a branched C 3  to C 12  alkyl group. 
       
     
     
         4 . The compound of  claim 1 , wherein the hindered phenol is a compound chosen from 2-tert-butylphenol; 2,6-ditert-butylphenol; 2-isopropylphenol; 2,6diisopropylphenol; 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. 
     
     
         5 . The compound of  claim 1 , wherein the hindered phenol is 2,6 di-tert butyl phenol. 
     
     
         6 . The compound of  claim 1 , wherein the diaryldiamine is a compound of the formula III, 
       
         
           
           
               
               
           
         
         where Ar and Ar′ each independently represent a substituted or unsubtituted aryl group having from 6 to 50 carbon atoms; and 
         R 6  is an amine substituent. 
       
     
     
         7 . The compound of  claim 6 , wherein R 5  is a substituent chosen from —NH 2 , —[NH(CH 2 ) n ] m NH 2 , —(CH 2 ) n NH 2 , and —CH 2 -aryl-NH 2 , in which n and m are each an integer having a value of from about 1 to about 20. 
     
     
         8 . The compound of  claim 7 , wherein at least one of Ar and Ar′ is substituted with one or more substituents in addition to R 5 , the one or more additional substituents being chosen from primary amine substituents, aliphatic hydrocarbon groups, hydroxyl groups, carboxyl groups, and nitro groups. 
     
     
         9 . The compound of  claim 6 , wherein Ar and Ar′ are phenyl groups. 
     
     
         10 . The compound of  claim 1 , wherein the diaryldiamine is a compound chosen from N-phenyl-1,3-phenylenediamine, N-phenyl-1,2-phenylenediamine and N-phenyl-1,4-phenylenediamine. 
     
     
         11 . The compound of  claim 1 , wherein the aldehyde is chosen from formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, valeraldehyde, caproaldehyde, heptaldehyde, stearaldehyde, benzaldehyde, salicylaldehyde, furfural, thiophene aldehyde, and paraformaldehyde. 
     
     
         12 . A compound of formula V, 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are independently chosen from hydrogen and hydrocarbyl groups, with the proviso that at least one of R 1  and R 2  is a hydrocarbyl group; 
         R 3  and R 4  are independently chosen from hydrogen and a linear or branched C 1  to C 12  alkyl group, with the proviso that at least one of R 3  and R 4  is a branched to C 3  to C 12  alkyl group; 
         ′R 5  is a secondary amine substituent; 
         R 5  and R 7  are independently chosen from hydrogen, C 1  to C 18  linear, branched or cyclic alkyl groups, substituted or unsubstituted heterocyclic groups, or substituted or unsubstituted aryl groups, and 
         Ar and Ar′ are groups independently chosen from substituted or unsubtituted aryl groups having from 6 about 50 carbon atoms. 
       
     
     
         13 . A process for forming a compound, the process comprising reacting (i) a hydrocarbyl phenol, (ii) a hindered phenol, (iii) a diaryldiamine and (iv) an aldehyde. 
     
     
         14 . The process of  claim 13 , wherein the hydrocarbyl phenol is a compound of the formula I, 
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  are chosen from hydrogen or hydrocarbyl groups, with the proviso that at least one of R 1  and R 2  is hydrocarbyl group. 
     
     
         15 . The process of  claim 13 , wherein the hindered phenol is a compound of the formula II, 
       
         
           
           
               
               
           
         
         where R 3  and R 4  are independently chosen from hydrogen or a linear or branched C 1  to C 12  alkyl group, with the proviso that at least one of R 3  and R 4  is a branched C 3  to C 12  alkyl group. 
       
     
     
         16 . The process of  claim 13 , wherein the diaryldiamine is a compound of the formula III, 
       
         
           
           
               
               
           
         
         where Ar and Ar′ each independently represent a substituted or unsubtituted aryl group having from 6 to 50 carbon atoms; and 
         R 5  is an amine substituent. 
       
     
     
         17 . The process of  claim 13 , wherein the aldehyde is chosen from formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, valeraldehyde, caproaldehyde, heptaldehyde, stearaldehyde, benzaldehyde, salicylaldehyde, furfural, thiophene aldehyde, and paraformaldehyde. 
     
     
         18 . A lubricant composition comprising:
 a base oil; and   a first compound that is the reaction product of (i) a hydrocarbyl phenol, (ii) a hindered phenol, (iii) a diaryldiamine and (iv) an aldehyde.   
     
     
         19 . The lubricant composition of  claim 18 , wherein the concentration of the first compound ranges from about 0.05 wt % to about 10 wt % of the lubricant composition. 
     
     
         20 . The lubricant composition of  claim 18 , further comprising one or more additional additives chosen from dispersants, detergents, anti-wear agents, supplemental antioxidants, viscosity index improvers, pour point depressants, corrosion inhibitors, rust inhibitors, foam inhibitors, anti-swell agents and friction modifiers. 
     
     
         21 . The lubricant composition of  claim 18 , wherein:
 the hydrocarbyl phenol is a compound of the formula I,   
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are chosen from hydrogen or hydrocarbyl groups, with the proviso that at least one of R 1  and R 2  is a hydrocarbyl group; 
         the hindered phenol is a compound of the formula II, 
       
       
         
           
           
               
               
           
         
         where R 3  and R 4  are independently chosen from hydrogen and a linear or branched C 1  to C 12  alkyl group, with the proviso that at least one of R 3  and R 4  is a branched C 3  to C 12  alkyl group; 
         the diaryldiamine is a compound of the formula III, 
       
       
         
           
           
               
               
           
         
         where Ar and Ar′ each independently represent a substituted or unsubtituted aryl group having from 6 to 50 carbon atoms and R 5  is an amine substituent; and 
         the aldehyde is chosen from formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, valeraldehyde, caproaldehyde, heptaldehyde, stearaldehyde, benzaldehyde, salicylaldehyde, furfural, thiophene aldehyde, and paraformaldehyde. 
       
     
     
         22 . The lubricant composition of  claim 21 , wherein R 5  is a substituent chosen from —NH 2 , —[NH(CH 2 ) n ] m NH 2 , —(CH 2 ) n NH 2 , and —CH 2 -aryl-NH 2 , in which n and m are each an integer having a value of from about 1 to about 20; and wherein Ar and Ar′ are phenyl groups. 
     
     
         23 . The lubricant composition of  claim 21 , wherein the hindered phenol is a compound 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. 
     
     
         24 . The lubricant composition of  claim 21 , wherein the diaryldiamine is a compound chosen from N-phenyl-1,3-phenylenediamine, N-phenyl-1,2-phenylenediamine and N-phenyl-1,4-phenylenediamine. 
     
     
         25 . A additive package composition comprising:
 a diluent; and   a first compound that is the reaction product of (i) a hydrocarbyl phenol, (ii) a hindered phenol, (iii) a diaryldiamine and (iv) an aldehyde.   
     
     
         26 . The additive package composition of  claim 25 , wherein the concentration of the first compound ranges from about 5 wt % to about 75 wt % of the additive package composition. 
     
     
         27 . The additive package composition of  claim 25 , further comprising one or more additional additives chosen from dispersants, detergents, anti-wear agents, supplemental antioxidants, viscosity index improvers, pour point depressants, corrosion inhibitors, rust inhibitors, foam inhibitors, anti-swell agents and friction modifiers. 
     
     
         28 . The additive package of  claim 25 , wherein:
 the hydrocarbyl phenol is a compound of the formula I,   
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are chosen from hydrogen or hydrocarbyl groups, with the proviso that at least one of R 1  and R 2  is a hydrocarbyl group; 
         the hindered phenol is a compound of the formula II, 
       
       
         
           
           
               
               
           
         
         where R 3  and R 4  are independently chosen from hydrogen and a linear or branched C 1  to C 12  alkyl group, with the proviso that at least one of R 3  and R 4  is a branched C 3  to C 12  alkyl group; 
         the diaryldiamine is a compound of the formula III, 
       
       
         
           
           
               
               
           
         
         where Ar and Ar′ each independently represent a substituted or unsubtituted aryl group having from 6 to 50 carbon atoms and R 5  is an amine substituent; and 
         the aldehyde is chosen from formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, valeraldehyde, caproaldehyde, heptaldehyde, stearaldehyde, benzaldehyde, salicylaldehyde, furfural, thiophene aldehyde, and paraformaldehyde. 
       
     
     
         29 . The additive package of  claim 28 , wherein R 5  is a substituent chosen from —NH 2 , —[NH(CH 2 ) n ] m NH 2 , —(CH 2 ) n NH 2 , and —CH 2 -aryl-NH 2 , in which n and m are each an integer having a value of from about 1 to about 20; and wherein Ar and Ar′ are phenyl groups. 
     
     
         30 . The additive package of  claim 28 , wherein the hindered phenol is a compound 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. 
     
     
         31 . The additive package of  claim 28 , wherein the diaryldiamine is a compound chosen from N-phenyl-1,3-phenylenediamine, N-phenyl-1,2-phenylenediamine and N-phenyl-1,4-phenylenediamine. 
     
     
         32 . 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 according to  claim 18 , where the amount of oxidation of the oil is reduced compared to the amount of oxidation that would have occurred if the lubricating composition did not comprise the first compound.