Hydrocarbyl succinic acid and hydrocarbylsuccinic acid derivatives as friction modifiers

Abstract

The present invention relates to hydrocarbyl succinic acid and hydrocarbylsuccinic acid derivatives as friction modifiers for gasolines.

1 . The use of at least one hydrocarbyl succinic acid or hydrocarbyl succinic acid derivative of the formula (I) 
     
       
         
         
             
             
         
       
       wherein
 R 1  is an aliphatic hydrocarbyl group containing less than 15% quaternary carbon atoms, or is an araliphatic hydrocarbyl group; 
 X and Y are, independently of each other, OR 2 , O − (M x+ ) 1/x  or NR 3 R 4  or X and Y together form a group —O—; 
 R 2  is hydrogen, C 1 -C 8 -alkyl, aryl or C 1 -C 20 -alkylaryl; 
 R 3  and R 4  are, independently of each other, hydrogen, C 1 -C 8 -alkyl, C 2 -C 8 -hydroxyalkyl, C 2 -C 8 -alkylene-NR 6 R 7 , a group of the formula A-NR 8  y A-NR 6 R 7 , aryl or C 1 -C 20 -alkylaryl; where
 R 6 , R 7  and R 8  are, independently of each other, hydrogen, C 1 -C 8 -alkyl or C 2 -C 8 -hydroxyalkyl; 
 A is a C 2 -C 4 -alkylene group; and 
 y is 0 or an integer from 1 to 10; 
 
 (M x+ ) 1/x  a metal equivalent, an ammonium cation [NH 4 ] +  or a substituted ammonium cation equivalent; and 
 x is 1, 2, 3 or 4 in case (M x+ ) 1/x  a metal equivalent, or is 1 in case (M x+ ) 1/x  an ammonium cation [NH 4 ] +  or is an integer from 1 to 10 in case (M x+ ) 1/x  is a substituted ammonium cation equivalent, 
 
       as friction modifying additive in a gasoline. 
     
   
   
       2 . The use as claimed in  claim 1 , where R 1  is a linear or branched C 4 -C 40 -alkenyl or C 4 -C 40 -alkyl group, wherein at least 95% of the carbon atoms are no quaternary, or R 1  is a C 1 -C 20 -alkylaryl group. 
   
   
       3 . The use as claimed in  claim 2 , where R 1  is derived from an α-alkene. 
   
   
       4 . The use as claimed in  claim 2 , where R 1  is derived from a polyalkene obtained by oligo- or polymerization of at least one C 2 -C 8 -alkene. 
   
   
       5 . The use as claimed in  claim 1 , where R 2  is hydrogen or C 1 -C 8 -alkyl. 
   
   
       6 . The use as claimed in  claim 1 , where R 3  and R 4  are, independently of each other, hydrogen, C 1 -C 8 -alkyl, C 2 -C 8 -hydroxyalkyl, C 2 -C 8 -alkylene-NR 6 R 7  or a group of the formula A-NR 8  y A-NR 6 R 7 , where R 6 , R 7 , R 8 , A and y are as defined in  claim 1   
   
   
       7 . The use as claimed in  claim 1 , where
 (M x+ ) 1/x  an alkali metal cation, an alkaline earth metal equivalent, an ammonium cation [NH 4 ] +  or a substituted ammonium cation equivalent;   x is 1 or 2 in case (M x+ ) 1/x  an alkali metal or alkaline earth metal equivalent, or is 1 in case (M x+ ) 1/x  is an ammonium cation [NH 4 ] +  or is an integer from 1 to 10 in case (M x+ ) 1/x  a substituted ammonium cation equivalent   
   
   
       8 . The use as claimed in  claim 1 , where
 X and Y are, independently of each other, OR 2 , O − (M x+ ) 1/x , NR 3 R 4  or X and Y together form a group —O—;   R 2  is hydrogen or C 1 -C 8 -alkyl;   R 3  and R 4  are, independently of each other, hydrogen, C 1 -C 8 -alkyl, C 2 -C 8 -hydroxyalkyl, C 2 -C 8 -alkylene-NR 6 R 7  or a group of the formula A-NR 8  y A-NR 6 R 7 ;   (M x+ ) 1/x  is an alkali metal cation, an alkaline earth metal equivalent, an ammonium cation [NH 4 ] +  or a substituted ammonium cation equivalent;   x is 1 or 2 in case (M x+ ) 1/x  an alkali metal or alkaline earth metal equivalent, or is 1 in case (M x+ ) 1/x  is an ammonium cation [NH 4 ] +  or is an integer from 1 to 10 in case (M x+ ) 1/x  a substituted ammonium cation equivalent; and   R 6 , R 7 , R 8 — A and y are as defined in  claim 1 .   
   
   
       9 . The use as claimed in  claim 8 , where X and Y are, independently of each other, OH or O − (M x+ ) 1/x , or together form a group —O—. 
   
   
       10 . The use as claimed in  claim 9 , where X and Y are, independently of each other, OH or O − (M x+ ) 1/x . 
   
   
       11 . The use as claimed in  claim 1 , where the substituted ammonium cation equivalent is derived from a monoamine NR 10 R 11 R 12 , from a diamine of the formula NR 13 R 14 —C 2 -C 8 -alkylene-NR 6 R 7 , or from a polyamine of the formula NR 13 R 14 A-NR 8  w A-NR 6 R 7 ,
 where
 R 10 , R 11 , and R 12  are, independently of each other, hydrogen, C 1 -C 20 -alkyl or C 2 -C 8 -hydroxyalkyl, with the proviso that at least one of the radicals R 10 , R 11 , and R 12  is different from hydrogen; 
 R 13  and R 14  are, independently of each other, hydrogen, C 1 -C 8 -alkyl or C 2 -C 8 -hydroxyalkyl; 
 w is an integer from 1 to 8; and 
 R 6 , R 7 , R 8  and A are as defined in any of  claims 1  to  4 . 
   
   
   
       12 . The use as claimed in  claim 1 , where the compound of formula (I) is a hydrocarbyl succinic acid of the formula (I-1) 
     
       
         
         
             
             
         
       
       which is at least partially neutralized by a monoamine NR 10 R 11 R 12  or a diamine NR 13 R 14 —C 2 -C 8 -alkylene-NR 6 R 7  or a polyamine of the formula NR 13 R 14 A-NR 8  w A-NR 6 R 7 , 
       where 
       R 10 , R 11 , and R 12  are, independently of each other, hydrogen, C 1 -C 20 -alkyl or C 2 -C 8 -hydroxyalkyl, with the proviso that at least one of the radicals R 10 , R 11 , and R 12  is different from hydrogen 
       R 13 , and R 14  are, independently of each other, hydrogen, C 1 -C 8 -alkyl or C 2 -C 8 -hydroxyalkyl; 
       w is an integer from 1 to 8; and 
     
     R 1 , R 6 , R 7 , R 8  and A are as defined in any of  claims 1  to  4 . 
   
   
       13 . The use as claimed in  claim 1 , where the compound of formula (I) is a hydrocarbyl succinic acid of the formula (I-1) 
     
       
         
         
             
             
         
       
       where R 1  is as defined in any of  claims 1  to  4 . 
     
   
   
       14 . The use as claimed in  claim 1 , where the gasoline is additized with the compound of formula (I) in an amount of from 10 to 300 mg per kg of the gasoline. 
   
   
       15 . The use as claimed in  claim 1 , in combination with at least one further conventional fuel additive. 
   
   
       16 . Gasoline composition containing a gasoline as major component and at least one compound of the formula (I) as defined in  claim 1  and optionally at least one further additive. 
   
   
       17 . Additive concentrate, comprising at least one compound of the formula (I) as defined in  claim 1  and at least one diluent and optionally at least one further additive. 
   
   
       18 . A method for producing a gasoline composition with improved friction properties, where a gasoline or a commercial gasoline composition is additized with at least one compound of the formula (I) as defined in  claim 1 . 
   
   
       19 . The method according to  claim 17  with the additive concentrate of at least one diluent and optionally at least one further additive.