Functionalized Maleated Fatty Acids as Non Acidic Fluid Additives

Abstract

Maleated fatty acids that are functionalized with materials such as polyols, alkanolamines and/or alkylene oxides have been discovered to improve the properties of various fluids. In a non-limiting example, functionalized maleated fatty acids having acid numbers less than 10 may improve the lubricity of fuels and lubricants, such as hydrocarbon fuels and lubricants, when added thereto.

What is claimed is: 
     
         1 . A method of improving the lubricity of a fuel, the method comprising:
 adding to the fuel an effective amount of a functionalized maleated fatty acid that is an ester, imide, and/or amide to improve the lubricity thereof.   
     
     
         2 . The method  claim 1  where the functionalized maleated fatty acid is made by a process comprising:
 reacting an unsaturated fatty acid with an unsaturated compound selected from the group consisting of an unsaturated anhydride, a maleimide, and mixtures thereof where the unsaturated compound may be substituted with a linear or branched alkyl group, which reacting gives a maleated fatty acid; 
 reacting the maleated fatty acid with a multifunctional reactant selected from the group consisting of a polyol, an alkanolamine, an alkylene oxide and mixtures thereof to give a functionalized maleated fatty acid that has an acid number less than 10. 
 
     
     
         3 . The method of  claim 1  where the functionalized maleated fatty acid has a structure selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         where:
 R 1  is H or a hydrocarbyl group having 1 to 10 carbon atoms with zero, one or more double bonds, 
 R 2  is a direct bond or hydrocarbyl group having 1 to 10 carbons with one or more double bonds, 
 R 3  is —(CH 2 CH 2 O) n —, or —(CH 2 CH(CH 3 )O) n —, or combinations thereof, 
 
         R 4  is —(CH 2 CH 2 O) n H, —(CH 2 CH(CH 3 )O) n H, —CH 2 CHOHCH 2 OH, or —CH 2 CH 2 CH 2 CH 2 OH or combinations thereof, and 
         n is an integer from 1 to 10. 
       
     
     
         4 . The method of  claim 3  where the n is an integer from 1 to 5. 
     
     
         5 . The method of  claim 1  where the functionalized maleated fatty ester/imide/amide has an acid number less than 5. 
     
     
         6 . The method of  claim 2  where the effective amount of functionalized maleated fatty acid added to the fuel ranges from about 1 to about 3000 ppm. 
     
     
         7 . The method of  claim 2  where the unsaturated fatty acid has a weight average molecular weight between about 300 to about 5000. 
     
     
         8 . The method of  claim 6  where the unsaturated fatty acid is selected from the group consisting of monomeric, dimeric, trimeric crosslinked unsaturated fatty acids and mixtures thereof. 
     
     
         9 . The method of  claim 2  where the molar ratio of unsaturated fatty acid to unsaturated compound ranges from about 1:50 to about 50:1. 
     
     
         10 . The method of  claim 2  where the molar ratio of maleated fatty acid to multifunctional reactant ranges from about 1:20 to about 20:1. 
     
     
         11 . The method of  claim 2  where:
 the unsaturated fatty acid is selected from the group consisting of oleic acid, linoleic acid, a-linolenic acid, arachidonic acid, C10 to C40 unsaturated synthetic dimer fatty acids, dimer acid, unsaturated fatty acids having from 2 to 30 carbon atoms, and mixtures thereof; 
 the polyol is selected from the group consisting of glycol, glycerol, alkyl phenols, alkyoxylated alkyl phenol, linear or branched alkyl alcohols, the polyol having from 2 to 30 carbon atoms and mixtures thereof; 
 the alkanolamine is selected from the group consisting of ethanolamine, propanolamine, diethanolamine, n-alkylethanolamine, isopropanol amine, diisopropanol amine, 3-amino-1,2-propanediol and mixtures thereof; and 
 the alkylene oxide is selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide and mixtures thereof. 
 
     
     
         12 . A method of improving the properties of a fluid selected from the group consisting of:
 reducing the corrosivity of a fluid selected from the group consisting of a fuel, a lubricant, a motor oil, a transmission fluid, and an alcohol; and   improving the lubricating properties of a lubricant, a motor oil, a transmission fluid, and an alcohol;   
       the method comprising adding to the fluid an effective amount of a functionalized maleated fatty acid that is an ester, imide, and/or amide to either improve the lubricity and or reduce the corrosivity thereof. 
     
     
         13 . The method of  claim 12  where the functionalized maleated fatty acid is made by a process comprising:
 reacting an unsaturated fatty acid with an unsaturated compound selected from the group consisting of an unsaturated anhydride, a maleimide, and mixtures thereof where the unsaturated compound may be substituted with a linear or branched alkyl group, which reacting gives a maleated fatty acid; 
 reacting the maleated fatty acid with a multifunctional reactant selected from the group consisting of a polyol, an alkanolamine, an alkylene oxide and mixtures thereof to give a functionalized maleated fatty acid that has an acid number less than 10. 
 
     
     
         14 . The method of  claim 12  where the method is for reducing the corrosivity of a fuel, and the effective amount of functionalized maleated fatty ester/imide/amide ranges from about 1 to about 100 ppm. 
     
     
         15 . The method of  claim 12  where the functionalized maleated fatty acid has a structure selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         where:
 R 1  is H or a hydrocarbyl group having 1 to 10 carbon atoms with zero, one or more double bonds, 
 R 2  is a direct bond or hydrocarbyl group having 1 to 10 carbons with one or more double bonds, 
 R 3  is —(CH 2 CH 2 O) n —, or —(CH 2 CH(CH 3 )O) n —, or combinations thereof, 
 
         R 4  is —(CH 2 CH 2 O) n H, —(CH 2 CH(CH 3 )O) n H, —CH 2 CHOHCH 2 OH, or —CH 2 CH 2 CH 2 CH 2 OH or combinations thereof, and 
         n is an integer from 1 to 10. 
       
     
     
         16 . The method of  claim 15  where the n is an integer from 1 to 5. 
     
     
         17 . The method of  claim 12  where the functionalized maleated fatty ester/imide/amide has an acid number less than 5. 
     
     
         18 . The method of  claim 12  where the effective amount of functionalized maleated fatty acid added to the fuel ranges from about 1 to about 3000 ppm. 
     
     
         19 . The method of  claim 13  where the unsaturated fatty acid has a weight average molecular weight between about 300 to about 5000 and where the unsaturated fatty acid is selected from the group consisting of monomeric, dimeric, trimeric crosslinked unsaturated fatty acids and mixtures thereof. 
     
     
         20 . The method of  claim 13  where the molar ratio of unsaturated fatty acid to unsaturated compound ranges from about 1:50 to about 50:1. 
     
     
         21 . The method of  claim 13  where the molar ratio of maleated fatty acid to multifunctional reactant ranges from about 1:20 to about 20:1. 
     
     
         22 . The method of  claim 13  where:
 the unsaturated fatty acid is selected from the group consisting of oleic acid, linoleic acid, a-linolenic acid, arachidonic acid, C10 to C40 unsaturated synthetic dimer fatty acids, unsaturated fatty acids having from 2 to 30 carbon atoms, and mixtures thereof; 
 the polyol is selected from the group consisting of glycol, glycerol, alkyl phenols, alkyoxylated alkyl phenol, linear or branched alkyl alcohols, the polyol having from 2 to 30 carbon atoms and mixtures thereof; 
 the alkanolamine is selected from the group consisting of ethanolamine, propanolamine, diethanolamine, n-alkylethanolamine, isopropanol amine, diisopropanol amine, 3-amino-1,2-propanediol and mixtures thereof; and 
 the alkylene oxide is selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide and mixtures thereof.