Acid-free quaternized nitrogen compounds and use thereof as additives in fuels and lubricants

Abstract

The present invention relates to novel acid-free quaternized nitrogen compounds, to the preparation thereof and to the use thereof as a fuel and lubricant additive, more particularly as a detergent additive, as a wax antisettling additive (WASA) or as an additive for reducing internal diesel injector deposits (IDID); to additive packages which comprise these compounds; and to fuels and lubricants thus additized. The present invention further relates to the use of these acid-free quaternized nitrogen compounds as a fuel additive for reducing or preventing deposits in the injection systems of direct-injection diesel engines, especially in common-rail injection systems, for reducing the fuel consumption of direct-injection diesel engines, especially of diesel engines with common-rail injection systems, and for minimizing power loss in direct-injection diesel engines, especially in diesel engines with common-rail injection systems.

1 . A quaternized nitrogen compound which is H +  donor-free, and comprises no inorganic acids or short-chain organic acids and is obtained by
 a. reacting a compound comprising at least one oxygen- or nitrogen-containing group reactive with an anhydride and at least one quaternizable amino group with a polycarboxylic anhydride compound to obtain an amide compound having at least one quaternizable amino group, and 
 b. quaternizing in the absence of a free acid the at least one quaternizable amino group of the amide compound by reaction with a hydrocarbyl epoxide of formula (II) to obtain the quaternized nitrogen compound: 
 
       
         
           
           
               
               
           
         
         wherein the R a  radicals are each independently H or a hydrocarbyl radical having 1 to 10 carbon atoms; and 
         wherein 
         at least the quaternizing is performed in the presence of a protic solvent, and 
         the quaternized nitrogen compound is selected from the group of compounds consisting of formulae Ia-1, Ia-2, Ia-3, Ib-1, Ib-2 and Ib-3: 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein R 1  is H or a straight-chain or branched hydrocarbyl radical which is optionally mono- or polysubstituted by hydroxyl, carboxyl, hydrocarbyloxy and/or acyl radicals, or has one or more ether groups in a hydrocarbyl chain; 
         R 2  is H or alkyl; 
         R 3  is hydrocarbyl, especially long-chain hydrocarbyl, for example a polyalkylene radical; 
         at least one of the R 4 , R 5  and R 6  radicals is a radical introduced by quaternization, and remaining radicals are selected from straight-chain or branched, cyclic hydrocarbyl radicals which are optionally mono- or polysubstituted and/or have one or more heteroatoms; 
         R 7  is H or a straight-chain or branched hydrocarbyl radical which is optionally mono- or polysubstituted by hydroxyl, carboxyl, hydrocarbyloxy and/or acyl radicals, or has one or more ether groups in the hydrocarbyl chain, or R 7  together with one of the R 4 , R 5  and R 6  radicals forms a bridge group; 
         L 1  is a chemical bond or a straight-chain or branched alkylene group and 
         L 2  is a straight-chain or branched alkylene group which optionally bears one or more heteroatoms or substituents. 
       
     
     
         2 . A fuel additive or lubricant additive comprising the quaternized nitrogen compound according to  claim 1 . 
     
     
         3 . A detergent additive for diesel fuels comprising the quaternized nitrogen compound according to  claim 1 . 
     
     
         4 . A wax antisetting additive (WASA) for middle distillate fuels comprising the quaternized nitrogen compound according to  claim 1 . 
     
     
         5 . An additive for reducing or preventing deposits in injection systems of direct-injection diesel engines comprising a quaternized nitrogen compound according to  claim 1 . 
     
     
         6 . An additive for controlling or reducing internal diesel injector deposits (IDID) comprising a quaternized nitrogen compound according to  claim 1 . 
     
     
         7 . An additive concentrate comprising, in combination with further diesel fuel additives, at least one quaternized nitrogen compound according to  claim 1 . 
     
     
         8 . A fuel composition comprising: a base fuel, and an effective amount of at least one quaternized nitrogen compound according to  claim 1 . 
     
     
         9 . A lubricant composition comprising: a lubricant, and
 an effective amount of at least one quaternized nitrogen compound according to  claim 1