Bicyclic thioamides as additives for lubricating oils

Abstract

A composition comprising: (a) from 0.1% to 20% of at least one bicyclic thioamide of formula I: wherein X is O, S, NR 6 or CR 7 R 8 ; R 1 , R 2 , R 4 , R 5 , R 7 and R 8 independently are hydrogen, alkyl, alkenyl, aryl or aralkyl; R 3 and R 6 independently are hydrogen, alkyl, alkenyl, aryl, aralkyl, alkanoyl or aroyl; and bond “a” is a single or double bond; and (b) a lubricating oil.

1 . A composition comprising: 
 (a) from 0.1% to 20% of at least one bicyclic thioamide of formula I:                          wherein X is O, S, NR 6  or CR 7 R 8 ; R 1 , R 2 , R 4 , R 5 , R 7  and R 8  independently are hydrogen, alkyl, alkenyl, aryl or aralkyl; R 3  and R 6  independently are hydrogen, alkyl, alkenyl, aryl, aralkyl, alkanoyl or aroyl; and bond “a” is a single or double bond; and    (b) a lubricating oil.    
     
     
         2 . The composition of  claim 1  in which at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7  and R 8  is aryl, aralkyl, C 4 -C 22  alkyl or C 4 -C 22  alkenyl.  
     
     
         3 . The composition of  claim 2  in which bond “a” is a double bond.  
     
     
         4 . The composition of  claim 3  in which R 3  is C 6 -C 22  alkyl, C 6 -C 22  alkenyl, aryl or aralkyl.  
     
     
         5 . The composition of  claim 4  in which X is NR 6 .  
     
     
         6 . The composition of  claim 2  in which bond “a” is a single bond.  
     
     
         7 . The composition of  claim 6  in which X is NR 6 .  
     
     
         8 . A composition comprising: 
 (a) a reaction product of a compound of formula (I) with an imine; an unsaturated carboxylic acid or ester; an isocyanate or isothiocyanate; or an alkyl, alkenyl or aralkyl group bearing a leaving group; and    (b) a lubricating oil.    
     
     
         9 . A compound of formula (IV)  
       
         
           
           
               
               
           
         
       
       wherein X is O, S, NR 6  or CR 7 R 8 ; R 1 , R 2 , R 4 , R 5 , R 7  and R 8  independently are hydrogen, alkyl, alkenyl, aryl or aralkyl; R 6  is B 3 , hydrogen, alkyl, alkenyl, aryl, aralkyl, alkanoyl or aroyl; bond “a” is a single or a double bond; bonds “b” and “c” are single or double bonds, provided that one of b and c is a single bond and the other is a double bond; 
 B 1 , B 2  and B 3  independently are —CR 12 H—CR 13 H—COOR 14 , —CR 10 R 11 NHR 9 , —C(O)NHR 15 , —C(S)NHR 15  or R 16 ; provided that at least one of B 1 , B 2  and B 3  is —CR 12 H—CR 13 H—COOR 14 , —CR 10 R 11 NHR 9 , —C(O)NHR 15 , —C(S)NHR 15  or R 16 ; and provided that when one of B 1  and B 2  is —CR 12 H-CR 13 H—COOR 14 , —CR 10 R 11 NHR 9 , —C(O)NHR 15 , —C(S)NHR 15  or R 16 , then the other of B 1  and B 2  is absent;  
 R 10 , R 11  and R 14  independently are hydrogen, alkyl, alkenyl, aryl or aralkyl; R 16  is alkyl, alkenyl or aralkyl; R 12  and R 13  independently are hydrogen or C 1 -C 4  alkyl; R 9  and R 15  independently are alkyl, alkenyl, aryl or aralkyl.  
 
     
     
         10 . The compound of  claim 9  in which at least one of B 1 , B 2  and B 3  is —CR 12 H—CR 13 H—COOR 14 , —CR 10 R 11 NHR 9 , —C(O)NHR 15  or —C(S)NHR 15 .