Compounds and Lubricating Compositions Containing the Compounds

Abstract

An imidazoline compound comprising the reaction product of (i) a dicarbonyl, (ii) a primary amine moiety of a polyamine, and (iii) a hydrocarbyl carbonyl is disclosed. Lubricant and fuel additive compositions comprising the imidazoline compound are also disclosed.

1 . An imidazoline compound comprising the reaction product of (i) a dicarbonyl, (ii) a primary amine moiety of a polyamine, and (iii) a hydrocarbyl carbonyl. 
     
     
         2 . The compound of  claim 1 , wherein the dicarbonyl is chosen from alpha-omega dicarboxylic acids, and esters thereof. 
     
     
         3 . The compound of  claim 1 , wherein the dicarbonyl is a compound of Formula I: 
       
         
           
           
               
               
           
         
         where n ranges from 0 to about 20; and
 R 1 , R 2 , R′ and R″ are independently chosen from a hydrogen atom and an alkyl group. 
 
       
     
     
         4 . The compound of  claim 3 , wherein at least one of R′ and R″ is an alkyl group. 
     
     
         5 . The compound of  claim 3 , where n is not 2 or 3. 
     
     
         6 . The compound of  claim 1 , wherein the dicarbonyl is a dicarboxylic acid chosen from oxalic acid, malonic acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, hexadecanedioic acid and isophthalic acid, and esters of any of these dicarboxylic acids. 
     
     
         7 . The compound of  claim 1 , wherein the dicarbonyl is dimethyl diethyl malonate. 
     
     
         8 . The compound of  claim 1 , wherein the polyamine is a linear, branched or cyclic polyalkyleneamine having at least one primary amine moiety. 
     
     
         9 . The compound of  claim 1 , wherein the polyamine is a compound of Formula II: 
       
         
           
           
               
               
           
         
       
       wherein R 6  is a hydrogen atom or a low molecular weight alkyl group having from about 1 to about 6 carbon atoms, q is an integer ranging from about 1 to about 3, and m is an integer ranging from about 2 to about 10. 
     
     
         10 . The compound of  claim 1 , wherein the polyamine is selected from the group consisting of propylene diamine, butylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, hexaethyleneheptamine, dipropylene triamine and tripropylene tetramine. 
     
     
         11 . The compound of  claim 1 , wherein the polyamine has at least three nitrogen atoms, and the compound is a reaction product of the hydrocarbyl carbonyl and a polyamine intermediate formed by reacting the dicarbonyl with the polyamine. 
     
     
         12 . The compound of  claim 11 , wherein the polyamine intermediate is formed by reacting the dicarbonyl with two equivalents of the polyamine. 
     
     
         13 . The compound of  claim 11 , wherein the polyamine intermediate comprises as least two unreacted primary amine moieties. 
     
     
         14 . The compound of  claim 11 , wherein the polyamine intermediate comprises a compound chosen from, 
       
         
           
           
               
               
           
         
       
       where n ranges from 0 to 20, m ranges from 2 to 10, x ranges from 1 to 11 and R′ and R″ are independently chosen from a hydrogen atom and an alkyl group. 
     
     
         15 . The compound of  claim 14 , wherein the hydrocarbyl carbonyl is a compound of the following Formula IV: 
       
         
           
           
               
               
           
         
       
       wherein R 14  is a hydrocarbyl group. 
     
     
         16 . The compound of  claim 15 , wherein R 14  is a polyolefin radical having a number average molecular weight ranging from about 350 to about 10,000 daltons. 
     
     
         17 . The compound of  claim 15 , wherein R 14  is polyisobutene. 
     
     
         18 . The compound of  claim 11 , wherein the hydrocarbyl carbonyl is chosen from hydrocarbyl substituted succinic anhydrides, hydrocarbyl substituted succinic acids, and esters of hydrocarbyl substituted succinic acids. 
     
     
         19 . The compound of  claim 1 , wherein the hydrocarbyl carbonyl is a compound of the following Formula IV: 
       
         
           
           
               
               
           
         
       
       wherein R 14  is a hydrocarbyl group. 
     
     
         20 . The compound of  claim 19 , wherein R 14  is a polyolefin radical having a number average molecular weight ranging from about 350 to about 10,000 daltons. 
     
     
         21 . The compound of  claim 19 , wherein R 14  is polyisobutene. 
     
     
         22 . The compound of  claim 1 , wherein the compound is a reaction product of the dicarbonyl and a mono-hydrocarbyl polyamine amine intermediate formed by reacting the hydrocarbyl carbonyl with the polyamine. 
     
     
         23 . An imidazoline compound comprising the reaction product of a dicarbonyl and a mono-hydrocarbyl polyamine, wherein the mono-hydrocarbyl polyamine is formed by reaction of a hydrocarbyl carbonyl and a polyamine. 
     
     
         24 . The compound of  claim 23 , wherein the dicarbonyl is a compound of Formula I: 
       
         
           
           
               
               
           
         
         where n ranges from 0 to about 20, with the proviso that n is not 2 or 3; and
 R 1 , R 2 , R′ and R″ are independently chosen from a hydrogen atom and an alkyl group. 
 
       
     
     
         25 . The compound of  claim 24 , wherein at least one of R′ and R″ is an alkyl group. 
     
     
         26 . The compound of  claim 23 , wherein the dicarbonyl is a dicarboxylic acid chosen from oxalic acid, malonic acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, hexadecanedioic acid and isophthalic acid, and esters of any of these dicarboxylic acids. 
     
     
         27 . The compound of  claim 23 , wherein the mono-hydrocarbyl polyamine is a compound of Formula V: 
       
         
           
           
               
               
           
         
         where R 14  is a hydrocarbyl group;
 R 6  is a hydrogen atom or a low molecular weight alkyl group having from about 1 to about 6 carbon atoms; 
 m is an integer ranging from about 2 to about 10; and 
 q is an integer ranging from about 1 to 3. 
 
       
     
     
         28 . The compound of  claim 23 , wherein the mono-hydrocarbyl polyamine is a fatty amine having at least one primary nitrogen atom. 
     
     
         29 . The compound of  claim 23 , wherein the hydrocarbyl carbonyl is a compound of the following Formula IV: 
       
         
           
           
               
               
           
         
       
       wherein R 14  is a hydrocarbyl group. 
     
     
         30 . The compound of  claim 29 , wherein R 14  is a polyolefin radical having a number average molecular weight ranging from about 350 to about 10,000 daltons. 
     
     
         31 . The compound of  claim 23 , wherein the hydrocarbyl carbonyl is chosen from dodecenylsuccinic anhydride, C 16-18  alkenyl succinic anhydride, and polyisobutenyl succinic anhydride. 
     
     
         32 . The compound of  claim 23 , wherein the polyamine is a linear, branched or cyclic polyalkyleneamine having at least one primary amine moiety. 
     
     
         33 . The compound of  claim 23 , wherein the polyamine is a compound of Formula II: 
       
         
           
           
               
               
           
         
       
       wherein R 6  is a hydrogen atom or a low molecular weight alkyl group having from about 1 to about 6 carbon atoms, q is an integer ranging from about 1 to about 3, and m is an integer ranging from about 2 to about 10. 
     
     
         34 . The compound of  claim 23 , wherein the polyamine is selected from the group consisting of propylene diamine, butylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, hexaethyleneheptamine, dipropylene triamine, and tripropylene tetramine. 
     
     
         35 . A lubricating composition comprising:
 a base oil; and   an imidazoline compound comprising the reaction product of (i) a dicarbonyl, (ii) a primary amine moiety of a polyamine, and (iii) a hydrocarbyl carbonyl.   
     
     
         36 . The lubricating composition of  claim 35 , wherein the concentration of the imidazoline compound ranges from about 0.1% by weight to about 20% by weight relative to the total weight of the composition. 
     
     
         37 . The lubricating composition of  claim 35 , wherein the dicarbonyl is a compound of Formula I: 
       
         
           
           
               
               
           
         
         where n ranges from 0 to about 20; and
 R 1 , R 2 , R′ and R″ are independently chosen from a hydrogen atom and an alkyl group. 
 
       
     
     
         38 . The lubricating composition of  claim 37 , wherein at least one of R′ and R″ is an alkyl group. 
     
     
         39 . The lubricating composition of  claim 37 , wherein the polyamine is a compound of Formula II: 
       
         
           
           
               
               
           
         
       
       wherein R 6  is a hydrogen atom or a low molecular weight alkyl group having from about 1 to about 6 carbon atoms, q is an integer ranging from about 1 to about 3, and m is an integer ranging from about 2 to about 10. 
     
     
         40 . The lubricating composition of  claim 35 , wherein the hydrocarbyl carbonyl is a compound of the following Formula IV: 
       
         
           
           
               
               
           
         
       
       wherein R 14  is a hydrocarbyl group. 
     
     
         41 . The lubricating composition of  claim 40 , wherein R 14  is polyisobutene. 
     
     
         42 . A method of reducing deposits on a lubricated surface, the method comprising lubricating the surface with the lubricating composition of  claim 35 , wherein the imidazoline compound is present in an amount sufficient to reduce the amount of deposits on the lubricated surface, as compared to the amount of deposits on the surface subjected to the same operating conditions and lubricated with the same lubricant composition except that the composition is devoid of the imidazoline compound. 
     
     
         43 . A method for improving the suspension of sludge comprising providing to a combustion system the lubricating composition of  claim 35 , wherein the imidazoline compound is present in an amount sufficient to maintain at least some sludge in suspension in the base oil for a period of time longer than if the base oil did not contain the imidazoline compound. 
     
     
         44 . A lubricant additive package composition comprising:
 a diluent; and   the imidazoline compound of  claim 1 .   
     
     
         45 . The additive package of  claim 44 , wherein the concentration of imidazoline compound ranges from about 5 to about 75 weight percent relative to the total weight of the additive package composition. 
     
     
         46 . The additive package of  claim 44 , further comprising one or more additional additives chosen from additional dispersants, detergents, anti-wear agents, supplemental antioxidants, viscosity index improvers, pour point depressants, corrosion inhibitors, rust inhibitors, foam inhibitors, and friction modifiers. 
     
     
         47 . A fuel composition comprising:
 a base fuel; and   an imidazoline compound comprising the reaction product of (i) a dicarbonyl, (ii) a primary amine moiety of a polyamine, and (iii) a hydrocarbyl carbonyl.   
     
     
         48 . The fuel composition of  claim 47 , wherein the concentration of the imidazoline compound ranges from about 10 to about 10,000 parts per million. 
     
     
         49 . The fuel composition of  claim 47 , wherein the dicarbonyl is a compound of Formula I: 
       
         
           
           
               
               
           
         
         where n ranges from 0 to about 20; and
 R 1 , R 2 , R′ and R″ are independently chosen from a hydrogen atom and an alkyl group. 
 
       
     
     
         50 . The fuel composition of  claim 47 , wherein the polyamine is a compound of Formula II: 
       
         
           
           
               
               
           
         
       
       wherein R 6  is a hydrogen atom or a low molecular weight alkyl group having from about 1 to about 6 carbon atoms, q is an integer ranging from about 1 to about 3, and m is an integer ranging from about 2 to about 10. 
     
     
         51 . The fuel composition of  claim 47 , wherein the hydrocarbyl carbonyl is a compound of the following Formula IV: 
       
         
           
           
               
               
           
         
       
       wherein R 14  is a hydrocarbyl group. 
     
     
         52 . The fuel composition of  claim 51 , wherein R 14  is polyisobutene. 
     
     
         53 . A method of reducing deposits in the fuel system of an internal combustion engine, the method comprising using as the fuel for the internal combustion engine the fuel composition of  claim 47 , wherein the imidazoline compound is present in the fuel in an amount sufficient to reduce the deposits in the fuel system, as compared to the amount of deposits in the fuel system operated in the same manner and using the same fuel composition except that the fuel composition is devoid of the imidazoline compound. 
     
     
         54 . A method of dispersing soot, comprising providing to a combustion system the fuel composition of  claim 47 , wherein the imidazoline compound is present in an amount sufficient to maintain at least some soot in suspension in the base fuel for a period of time longer than if the base fuel did not contain the imidazoline compound. 
     
     
         55 . A fuel additive package composition comprising:
 a diluent; and   the imidazoline compound of  claim 1 .   
     
     
         56 . The fuel additive package composition of  claim 55 , wherein the concentration of imidazoline compound ranges from about 5 weight percent to about 50 weight percent of the total fuel additive package composition. 
     
     
         57 . A process for forming an imidazoline compound comprising reacting (i) a dicarbonyl, (ii) a primary amine moiety of a polyamine, and (iii) a hydrocarbyl carbonyl. 
     
     
         58 . The process of  claim 57 , wherein the process comprises:
 (i) reacting the dicarbonyl with the polyamine under reaction conditions sufficient to form a polyamine imidazoline intermediate; and   (ii) reacting the polyamine imidazoline intermediate with the hydrocarbyl carbonyl.   
     
     
         59 . The process of  claim 58 , wherein the reaction conditions for forming the polyamine imidazoline intermediate include heating at reaction temperatures ranging from about 150° C. to about 250° C. 
     
     
         60 . A process for forming an additive compound comprising reacting a dicarbonyl compound and a mono-hydrocarbyl polyamine. 
     
     
         61 . The process of  claim 60 , wherein the dicarbonyl is a compound of Formula I: 
       
         
           
           
               
               
           
         
         where n ranges from 0 to about 20; and
 R 1 , R 2 , R′ and R″ are independently chosen from a hydrogen atom and an alkyl group. 
 
       
     
     
         62 . The process of  claim 60 , wherein the mono-hydrocarbyl polyamine is a fatty amine. 
     
     
         63 . The process of  claim 60 , wherein the mono-hydrocarbyl polyamine is formed by reacting a hydrocarbyl carbonyl with a polyamine. 
     
     
         64 . The process of  claim 63 , wherein the polyamine is a compound of Formula II: 
       
         
           
           
               
               
           
         
       
       wherein R 6  is a hydrogen atom or a low molecular weight alkyl group having from about 1 to about 6 carbon atoms, q is an integer ranging from about 1 to about 3, and m is an integer ranging from about 2 to about 10. 
     
     
         65 . The process of  claim 63 , wherein the hydrocarbyl carbonyl is a compound of the following Formula IV: 
       
         
           
           
               
               
           
         
       
       wherein R 14  is a hydrocarbyl group. 
     
     
         66 . The process of  claim 60 , wherein the additive compound comprises a central polyamine chain of one or more polyamine groups linked together with one or more groups chosen from diamide groups, imidazoline-amide groups and bis imidazoline groups, and a hydrocarbyl carbonyl group being attached to at least one end of the polyamine chain.