Carboxylic pyrrolidinones and methods of use thereof

Abstract

The present invention provides a compound comprising the reaction product of a hydrcarbyl substituted amine with an itaconate, such as an N-substituted 4-carboxypyrrolidin-2-one, and methods of employing the same in lubricating compositions. The lubricating compositions containing the N-substituted 4-carboxypyrrolidin-2-one are preferably intended to be employed in a method for lubricating a mechanical device, such as an automatic or manual transmission. However, it is envisioned that the compound can be employed in engine oil lubricants and any other type of functional fluid.

1 . A compound comprising the reaction product of a hydrcarbyl substituted amine with an itaconate. 
     
     
         2 . The compound as claimed in  claim 1  wherein the reaction product comprises an N-substituted 4-carboxypyrrolidin-2-one, wherein the substituent comprises a hydrocarbyl group or a heteroatom-containing hydrocarbyl group having at least about 8 carbon atoms, and esters or salts thereof. 
     
     
         3 . The compound of  claim 2  wherein the substituent comprises an alkyl group of about 8 to about 24 carbon atoms. 
     
     
         4 . The compound of  claim 2  wherein the substituent comprises a group containing at least one nitrogen atom. 
     
     
         5 . The compound of  claim 2  wherein the substituent comprises a group having one or more amino groups, wherein at least one amino group of said substituent group is further substituted by at least one alkyl group of about 8 to about 20 carbon atoms. 
     
     
         6 . The compound of  claim 5  wherein at least one amino group in said substituent is reacted with dimercaptothiadiazole or a derivative of a dimercaptothiadiazole. 
     
     
         7 . The reaction product of a compound as claimed in any of the previous claims further reacted at a carboxyl group on the compound with an amine or a hydrcarbyl substituted amine. 
     
     
         8 . A lubricant composition comprising an oil of lubricating viscosity and the compound of  claim 1 . 
     
     
         9 . The lubricant composition of  claim 8  wherein the compound of any of  claims 1  through  7  is present between 0.01 and 15 weight percent of the composition on an active basis. 
     
     
         10 . A method of lubricating a mechanical device by supplying thereto the lubricant of  claim 8 . 
     
     
         11 . The method of  claim 10  wherein the mechanical device comprises an automatic transmission. 
     
     
         12 . The method of  claim 10  wherein the mechanical device comprises an engine. 
     
     
         13 . The use of a compound as claimed in  claim 1  as an additive in a functional fluid. 
     
     
         14 . The use as claimed in  claim 13  wherein the additive is selected from at least one of a friction modifier and an antiwear agent.