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.

1 . A compound that is the reaction product of (i) a polyacrylate, (ii) a hindered phenol, (iii) a diaryldiamine and optionally (iv) an alkyl amine. 
     
     
         2 . The compound of  claim 1 , wherein the polyacrylate is a compound of the formula I, 
       
         
           
           
               
               
           
         
       
       where R 1  is an aliphatic or aromatic group, R 2  is hydrogen or methyl and q is an integer from about 2 to about 4. 
     
     
         3 . The compound of  claim 1 , wherein the polyacrylate is a compound chosen from 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, and propyleneglycol diacrylate. 
     
     
         4 . The compound of  claim 1 , 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. 
       
     
     
         5 . The compound of  claim 1 , 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. 
     
     
         6 . The compound of  claim 1 , wherein the hindered phenol is 2,6 di-tert butyl phenol. 
     
     
         7 . 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 about 6 to about 50 carbon atoms; and 
         R 5  is an amine substituent. 
       
     
     
         8 . The compound of  claim 7 , 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 10. 
     
     
         9 . 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. 
     
     
         10 . The compound of  claim 7 , wherein Ar and Ar′ are phenyl groups. 
     
     
         11 . 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. 
     
     
         12 . The compound of  claim 1 , wherein the compound is the reaction product of (i), (ii), (iii) and (iv), the alkyl amine being a compound of the formula IV, 
       
         
           
           
               
               
           
         
         where R 5  and R 7  are substituents independently chosen from hydrogen and saturated or olefinically unsaturated aliphatic alkyl groups, with the proviso that at least one of R 5  and R 7  is not hydrogen. 
       
     
     
         13 . The compound of  claim 1 , wherein the compound is the reaction product of (i), (ii), (iii) and (iv), the alkyl amine being a compound chosen from di-iso-amylamine, di-n-octylamine, di-(2ethylhexyl)amine, di-(tert-octyl)amine, di-n-nonylamine, dilauryl amine, di-hexadecylamine, di-octadecylamine, di-oleylamine; n-octylamine, 2-ethylhexylamine, tert-octylamine, n-decylamine, n-undecylamine, lauryl amine, hexadecylamine, heptadecylamine, octadecylamine, decenylamine, dodecenylamine, palmitoleylamine, oleylamine, linoleylamine, and eicosenylamine. 
     
     
         14 . A compound of formula V, 
       
         
           
           
               
               
           
         
         where Y is a group having a formula VI, 
       
       
         
           
           
               
               
           
         
         R 1  is an aliphatic or aromatic group, 
         R 2  is hydrogen or methyl, 
         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, 
         ′R 5  is a secondary amine substituent; 
         R 6  and R 7  are independently chosen from saturated or olefinically unsaturated aliphatic alkyl groups, and 
         Ar and Ar′ are groups independently chosen from substituted or unsubtituted aryl groups having from 6 to 50 carbon atoms. 
       
     
     
         15 . A process for forming a first compound, the process comprising combining (i) a polycrylate, (ii) a hindered phenol, (iii) a diaryldiamine and optionally (iv) an alkyl amine. 
     
     
         16 . The process of  claim 15 , wherein:
 the polyacrylate is a compound of the formula I,   
       
         
           
           
               
               
           
         
       
       where R 1  is an aliphatic or aromatic group, R 2  is hydrogen or methyl and q is an integer from 2 to 4;
 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; and 
         the diaryldiamine is a compound of the formula III, 
       
       
         
           
           
               
               
           
         
         where Ar and Ar′ each independently represent a substituted or unsubituted aryl group having from 6 to 50 carbon atoms, and R 5  is an amine substituent. 
       
     
     
         17 . The process of  claim 16 , wherein the first compound is prepared by combining the alkyl amine with (i), (ii) and (iii), the alkyl amine being a compound of the formula IV, 
       
         
           
           
               
               
           
         
         where R 6  and R 7  are substituents independently chosen from hydrogen and saturated or olefinically unsaturated aliphatic alkyl groups, with the proviso that at least one of R 6  and R 7  is not hydrogen. 
       
     
     
         18 . A lubricant composition comprising:
 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.   
     
     
         19 . The lubricant composition of  claim 18 , wherein the concentration of the 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 of  claim 18 , wherein:
 the polyacrylate is a compound of the formula I,   
       
         
           
           
               
               
           
         
       
       where R 1  is an aliphatic or aromatic group, R 2  is hydrogen or methyl and q is an integer from about 2 to about 4;
 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 5  and R 4  is a branched C 3  to C 12  alkyl group; and 
         the diaryldiamine is a compound of the formula III, 
       
       
         
           
           
               
               
           
         
         where Ar and Ar′ each independently represent a substituted or unsubstituted aryl group having from about 6 to about 50 carbon atoms; and 
         R 5  is an amine substituent. 
       
     
     
         22 . The lubricant 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 10. 
     
     
         23 . The lubricant of  claim 22 , wherein Ar and Ar′ are phenyl groups. 
     
     
         24 . The lubricant of  claim 21 , wherein the first compound that is the reaction product of (i), (ii), (iii), and (iv), the alkyl amine being a compound of the formula IV, 
       
         
           
           
               
               
           
         
         Where R 6  and R 7  are substituents independently chosen from hydrogen and saturated or olefinically unsaturated aliphatic alkyl groups, with the proviso that at least one of R 6  and R 7  is not hydrogen. 
       
     
     
         25 . The lubricant of  claim 18 , wherein:
 the polyacrylate is a compound chosen from 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, and propyleneglycol diacrylate;   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; and   the diaryldiamine is a compound chosen from N-phenyl-1,3-phenylenediamine, N-phenyl-1,2-phenylenediamine, and N-phenyl-1,4-phenylenediamine.   
     
     
         26 . The lubricant of  claim 25 , wherein the first compound is the reaction product of (i), (ii), (iii) and (iv), the alkyl amine being a compound chosen from di-iso-amylamine, di-n-octylamine, di-(2ethylhexyl)amine, di-(tert-octyl)amine, di-n-nonylamine, dilauryl amine, di-hexadecylamine, di-octadecylamine, di-oleylamine; n-octylamine, 2-ethylhexylamine, tert-octylamine, n-decylamine, n-undecylamine, lauryl amine, hexadecylamine, heptadecylamine, octadecylamine, decenylamine, dodecenylamine, palmitoleylamine, oleylamine, linoleylamine, and eicosenylamine. 
     
     
         27 . The lubricant of  claim 25 , wherein:
 the polyacrylate is TMPTA;   the hindered phenol is 2,6 di-tert butyl phenol; and   the diaryldiamine is a compound chosen from N-phenyl-1,3-phenylenediamine, N-phenyl-1,2-phenylenediamine, and N-phenyl-1,4-phenylenediamine.   
     
     
         28 . A lubricant composition comprising:
 a base oil; and   the compound of  claim 14 .   
     
     
         29 . An additive package comprising:
 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.   
     
     
         30 . The additive package of  claim 29 , wherein the concentration of the compound ranges from about 5 wt % to about 75 wt % of the additive package. 
     
     
         31 . The additive package composition of  claim 29 , 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. 
     
     
         32 . The additive package of  claim 29 , wherein:
 the polyacrylate is a compound of the formula I,   
       
         
           
           
               
               
           
         
       
       where R 1  is an aliphatic or aromatic group, R 2  is hydrogen or methyl and q is an integer from about 2 to about 4;
 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; and 
         the diaryldiamine is a compound of the formula III, 
       
       
         
           
           
               
               
           
         
         where Ar and Ar′ each independently represent a substituted or unsubtituted aryl group having from about 6 to about 50 carbon atoms; and 
         R 5  is an amine substituent. 
       
     
     
         33 . The additive package of  claim 32 , 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 10. 
     
     
         34 . The additive package of  claim 33 , wherein Ar and Ar′ are phenyl groups. 
     
     
         35 . The additive package of  claim 32 , wherein the first compound is the reaction product of (i), (ii), (iii) and (iv), the alkyl amine being a compound of the formula IV, 
       
         
           
           
               
               
           
         
         where R 6  and R 7  are substituents independently chosen from hydrogen and saturated or olefinically unsaturated aliphatic alkyl groups, with the proviso that at least one of R 6  and R 7  is not hydrogen. 
       
     
     
         36 . The additive package of  claim 29 , wherein:
 the polyacrylate is a compound chosen from 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, and propyleneglycol diacrylate;   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; and   the diaryldiamine is a compound chosen from N-phenyl-1,3-phenylenediamine, N-phenyl-1,2-phenylenediamine, and N-phenyl-1,4-phenylenediamine.   
     
     
         37 . The additive package of  claim 36 , wherein the first compound is the reaction product of (i), (ii), (iii) and (iv), the alkyl amine being a compound chosen from di-iso-amylamine, di-n-octylamine, di-(2ethylhexyl)amine, di-(tert-octyl)amine, di-n-nonylamine, dilauryl amine, di-hexadecylamine, di-octadecylamine, di-oleylamine; n-octylamine, 2-ethylhexylamine, tert-octylamine, n-decylamine, n-undecylamine, lauryl amine, hexadecylamine, heptadecylamine, octadecylamine, decenylamine, dodecenylamine, palmitoleylamine, oleylamine, linoleylamine, and eicosenylamine. 
     
     
         38 . The additive package of  claim 36 , wherein:
 the polyacrylate is TMPTA;   the hindered phenol is 2,6 di-tert butyl phenol; and   the diaryldiamine is a compound chosen from N-phenyl-1,3-phenylenediamine, N-phenyl-1,2-phenylenediamine, and N-phenyl-1,4-phenylenediamine.   
     
     
         39 . A additive package composition comprising:
 a base oil; and   the compound of  claim 14 .   
     
     
         40 . 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 .