Friction modifier for hydrocarbon fuels

Abstract

There is provided a friction modifier of the formula R 1 L-N(R 2 )(R 3 ) wherein R 1 is a hydrocarbyl group that has a number average molecular weight (Mn) of from 500 to 5000; L is an optional linker group; and R 2 and R 3 are independently selected from H, a hydrocarbyl group and a bond to optional group L, wherein at least one of R 2 and R 3 is H or a hydrocarbyl group, with the proviso that if one of R 2 and R 3 is a hydrocarbyl group and the other of R 2 and R 3 is H, the hydrocarbyl group does not contain a terminal amine.

1 . A friction modifier represented by the formula  
       R 1 -L-N(R 2 )(R 3 )  
     wherein R 1  is a hydrocarbyl group and has a number average molecular weight (Mn) of from 500 to 5000; 
 L is an optional linker group; and  
 R 2  and R 3  are independently selected from H, a hydrocarbyl group and a bond to optional group L, wherein at least one of R 2  and R 3  is H or a hydrocarbyl group, with the proviso that if one of R 2  and R 3  is a hydrocarbyl group and the other of R 2  and R 3  is H, the hydrocarbyl group does not contain a terminal amine.  
 
   
   
       2 . A friction modifier according to  claim 1  wherein R 1  is a hydrocarbon group.  
   
   
       3 . A friction modifier according to  claim 1  wherein R 1  is a branched or straight chain alkyl group.  
   
   
       4 . A friction modifier according to  claim 3  wherein R 1  is a branched alkyl group.  
   
   
       5 . A friction modifier according to  claim 2  wherein R 1  is polyisobutene.  
   
   
       6 . A friction modifier according to  claim 1  wherein R 1  has a molecular weight of from 800 to 1300.  
   
   
       7 . A friction modifier according to  claim 5  wherein R 1  is polyisobutene having a molecular weight of from 800 to 1300.  
   
   
       8 . A friction modifier according to  claim 1  wherein group R 1  has from 10 to 200 carbons.  
   
   
       9 . A friction modifier according to  claim 1  wherein group R 1  has from 10 to 100 carbons.  
   
   
       10 . A friction modifier according to  claim 1  which comprises linker L.  
   
   
       11 . A friction modifier according to  claim 1  wherein L when bonded to N(R 2 )(R 3 ) provides a cyclic group of formula:  
     
       
         
         
             
             
         
       
     
     wherein e and f are independently an integer of from 0 to 6.  
   
   
       12 . A friction modifier according to  claim 1  wherein both R 2  and R 3  are H.  
   
   
       13 . A friction modifier according to  claim 1  wherein at least one of R 2  and R 3  is a hydrocarbyl group.  
   
   
       14 . A friction modifier according to  claim 13  wherein at least one of R 2  and R 3  is a hydrocarbyl group terminated with a moiety selected from —CH 3 , ═CH 2 , —OH, —C(O)OH, and derivatives thereof.  
   
   
       15 . A friction modifier according to  claim 13  wherein at least one of R 2  and R 3  is a hydrocarbyl group of the formula —[R 4 NH] p R 5 X 
 wherein R 4  is an alkylene group having from 1 to 10 carbons    wherein R 5  is an alkylene group having from 1 to 10 carbons    wherein p is an integer from 0 to 10;    wherein X is selected from —CH 3 , —CH 2 ═CH 2 , —OH, and —C(O)OH.    
   
   
       16 . A friction modifier according to  claim 15  wherein R 4  is an alkylene group having from 1 to 5 carbons.  
   
   
       17 . A friction modifier according to  claim 15  wherein R 5  is an alkylene group having from 1 to 5 carbons.  
   
   
       18 . A friction modifier according to  claim 15  wherein at least one of R 2  and R 3  is a hydrocarbyl group of the formula —[(CH 2 ) q NH] p (CH 2 ) r X 
 wherein p is an integer from 0 to 10;    wherein q is an integer from 1 to 10;    wherein r is an integer from 1 to 10; and    wherein X is selected from —CH 3 , —CH 2 ═CH 2 , —OH, and —C(O)OH.    
   
   
       19 . A friction modifier according to  claim 18  wherein p is an integer from 1 to 10.  
   
   
       20 . A friction modifier according to  claim 18  wherein q is an integer from 1 to 10.  
   
   
       21 . A friction modifier according to  claim 18  wherein r is an integer from 1 to 10.  
   
   
       22 . A friction modifier according to  claim 15  wherein X is selected from —CH 3 , and —OH.  
   
   
       23 . A friction modifier according to  claim 15  wherein at least one of R 2  and R 3  is a group of the formula —(CH 2 ) 3 CH 3 .  
   
   
       24 . A friction modifier according to  claim 23  wherein one of R 2  and R 3  is a group of the formula —(CH 2 ) 3 CH 3 , and the other of R 2  and R 3  is H.  
   
   
       25 . A friction modifier according to  claim 15  wherein at least one of R 2  and R 3  is a group of the formula —(CH 2 ) 2 NH(CH 2 ) 2 OH.  
   
   
       26 . A friction modifier according to  claim 25  wherein one of R 2  and R 3  is a group of the formula —(CH 2 ) 2 NH(CH 2 ) 2 OH, and the other of R 2  and R 3  is H.  
   
   
       27 . A friction modifier according to  claim 1  which is a polyisobutenyl succinimide.  
   
   
       28 . A friction modifying composition comprising: 
 (i) a friction modifier according to  claim 1;     (ii) a carrier oil comprising an optionally esterified polyether.    
   
   
       29 . A friction modifying composition according to  claim 28  wherein the polyether carrier oil has a molecular weight in the range 500 to 5000.  
   
   
       30 . A friction modifying composition according to  claim 28  wherein the polyether carrier oil is a mono end-capped polypropylene glycol.  
   
   
       31 . A friction modifying composition according to  claim 30  wherein the end cap is a group consisting of or containing a hydrocarbyl group having up to 30 carbon atoms.  
   
   
       32 . A friction modifying composition according to  claim 31  wherein the end cap is or comprises an alkyl group having from 4 to 20 carbon atoms.  
   
   
       33 . A friction modifying composition according to  claim 30  wherein the carrier oil is a polypropyleneglycol monoether of the formula:  
     
       
         
         
             
             
         
       
     
     where R 6  is straight chain C 12-18  alkyl; and n is an integer of from 10 to 30.  
   
   
       34 . A friction modifying composition according to  claim 28  wherein the friction modifier is present in an amount of from 10 to 60% by weight, based on the total composition.  
   
   
       35 . A friction modifying composition according to  claim 28  wherein the carrier oil is present in an amount of from 10 to 40% by weight, based on the total composition.  
   
   
       36 . A friction modifying composition according to  claim 28  wherein the weight ratio of friction modifier to carrier oil is from 0.2:1 to 5:1.  
   
   
       37 . A friction modifying composition according to  claim 28  further comprising a solvent.  
   
   
       38 . A friction modifying composition according to  claim 37  wherein the solvent is a hydrocarbon solvent having a boiling point in the range 66 to 320° C.  
   
   
       39 . A fuel additive composition comprising: 
 (i) a friction modifier as defined in  claim 1;  and    (ii) a carrier, diluent or solvent;    which is substantially free of any detergent or friction modifier other than the friction modifier as defined in  claim 1 .    
   
   
       40 . A fuel additive composition according to  claim 39  which is substantially free of any detergent and any friction modifier other than the friction modifier as defined in  claim 1 .  
   
   
       41 . A fuel additive composition according to  claim 39  wherein the carrier, diluent or solvent is a carrier oil comprising an optionally esterified polyether.  
   
   
       42 . A fuel additive composition according  claim 39  wherein the carrier, diluent or solvent is a polyether carrier oil as defined in  claim 29 .  
   
   
       43 . A fuel composition comprising 
 (i) a fuel; and    (ii) a friction modifier according to  claim 1 .    
   
   
       44 . A fuel composition comprising 
 (i) a fuel; and    (ii) a friction modifying composition according to  claim 28 .    
   
   
       45 . A fuel composition comprising 
 (i) a fuel; and    (ii) a fuel additive composition according to  claim 39 .    
   
   
       46 . A fuel composition according to  claim 43  wherein the friction modifier is present in an amount, on a weight basis, of 50 to 500 ppm.  
   
   
       47 . A fuel composition according to  claim 44  wherein the friction modifying composition is present in an amount to provide on a weight basis, from 50 to 500 ppm friction modifier and 30 to 500 ppm carrier oil.  
   
   
       48 . A fuel composition according to  claim 43  wherein the fuel is a gasoline.  
   
   
       49 . A process for the reduction of friction in a combustion engine comprising the steps of: 
 (i) dosing a fuel with a friction modifier as defined in  claim 1 , or a friction modifying composition as defined in  claim 28 , or a fuel additive composition as defined in  claim 39 , to provide a fuel composition;    (ii) combusting the fuel composition in a combustion engine.    
   
   
       50 . A process according to  claim 49  wherein the fuel composition is substantially free of any detergent other than the friction modifier as defined in  claim 1 .  
   
   
       51 . A process according to  claim 49  wherein the fuel composition is substantially free of any friction modifier other than the friction modifier as defined in  claim 1 .  
   
   
       52 . Use of a friction modifier as defined in  claim 1 , or a friction modifying composition as defined  claim 28 , or a fuel additive composition as defined in  claim 39 , for reducing friction or improving detergency in a combustion engine.  
   
   
       53 . Use of a friction modifier as defined  claim 1 , or a friction modifying composition as defined in  claim 28 , or a fuel additive composition as defined in  claim 39 , for reducing friction and improving detergency in a combustion engine.  
   
   
       54 - 59 . (canceled)