Ortho-alkylphenol derived mannich detergent composition and concentrate, fuel and method thereof

Abstract

A detergent composition comprises a Mannich reaction product of a hydrocarbyl-substituted ortho-alkyl substituted phenol (1) or a mixture of the phenol (1) and a hydrocarbyl-substituted phenol (2), an aldehyde, and an amine where the phenol (1) is present in the mixture at about 50 mole % or higher. Concentrate and fuel compositions include the detergent composition. A method of controlling deposits in an internal combustion engine comprises operating the engine with the fuel composition which results in unexpectedly superior detergent performance.

1 . A detergent composition useful in hydrocarbon fuels, comprising: 
 a Mannich reaction product prepared by adding an aldehyde to a mixture of a phenol (1) having a hydrocarbyl substituent and an ortho-alkyl substituent; a phenol (2) having a hydrocarbyl substituent wherein the phenol (1) is present at about 50 mole % or higher in a combination of the phenol (1) and the phenol (2); and at least one amine selected from the group consisting of a primary monoamine, and a polyamine having at least two amino groups capable of undergoing a Mannich reaction wherein at least one of the amino groups is a primary amino group; and reacting the aldehyde; the phenol (1); the phenol (2); and the at least one amine to form the Mannich reaction product.    
     
     
         2 . A concentrate composition, comprising: 
 a solvent; and    the detergent composition of  claim 1 .    
     
     
         3 . A fuel composition, comprising. 
 a hydrocarbon fuel; and    the detergent composition of  claim 1 .    
     
     
         4 . The detergent composition of  claim 1;  wherein the phenol (1) is present at about 70 mole % or higher in the combination of the phenol (1) and the phenol (2).  
     
     
         5 . The detergent composition of  claim 4;  wherein the phenol (1) is present at about 80 mole % or higher in the combination of the phenol (1) and the phenol (2).  
     
     
         6 . The detergent composition of  claim 4;  wherein the ortho-alkyl substituent of the phenol (1) has 1 to about 10 carbon atoms.  
     
     
         7 . The detergent composition of  claim 6:  wherein the ortho-alkyl substituent of the phenol (1) has 1 carbon atom.  
     
     
         8 . The detergent composition of  claim 4;  wherein the hydrocarbyl substituent of the phenol (1) and the phenol (2) is derived from a polyolefin having a number average molecular weight of 200 to 5,000.  
     
     
         9 . The detergent composition of  claim 8;  wherein the hydrocarbyl substituent has a number average molecular weight of 200 to 750.  
     
     
         10 . The detergent composition of  claim 8;  wherein the polyolefin is a polyisobutene.  
     
     
         11 . The detergent composition of  claim 10;  wherein the polyisobutene has a vinylidene content of at least 70%.  
     
     
         12 . The detergent composition of  claim 4;  wherein the aldehyde is formaldehyde.  
     
     
         13 . The detergent composition of  claim 12;  wherein the amine is propylamine, butylamine, ethylenediamine, N-methylethylenediamine, propylenediamine, N-methylpropylenediamine, diethylenetriamine, ethanolamine, or 2-(2-aminoethyl-amino)ethanol.  
     
     
         14 . The detergent composition of 4; wherein the aldehyde has 2 to about 6 carbon atoms; and the at least one amine is selected from the group consisting of a primary monoamine, a secondary monoamine, and a polyamine having at least two amino groups capable of undergoing a Mannich reaction.  
     
     
         15 . A concentrate composition, comprising: 
 a solvent; and    the detergent composition of  claim 4 .    
     
     
         16 . The concentrate composition of  claim 15 , further comprising: 
 a carrier fluid.    
     
     
         17 . A fuel composition, comprising: 
 a hydrocarbon fuel; and    the concentrate composition of  claim 16 .    
     
     
         18 . A fuel composition, comprising: 
 a hydrocarbon fuel; and    the detergent composition of  claim 4 .    
     
     
         19 . The fuel composition of  claim 18;  wherein the hydrocarbon fuel is a gasoline, a diesel fuel, a biofuel, or a mixture of a diesel fuel and a biofuel.  
     
     
         20 . A method for controlling deposits in an internal combustion engine, comprising: 
 operating the engine with the fuel composition of  claim 18 .    
     
     
         21 . The method of  claim 20;  wherein the engine is a gasoline engine or a diesel engine.