Aminobenzoic Acid Derivatives

Abstract

This invention relates to N-alkylated anthranilic acid derivative and their use in lubricants, such as engine oils, as TBN boosters. The invention particularly relates to compositions that deliver an ash-free base to a lubricant in the form of a basic amine additive, without adversely impacting seal compatibility and/or degradation, and methods thereof.

We claim: 
     
         1 . A composition comprising (a) an oil of lubricating viscosity and (b) an additive of formula (I) 
       
         
           
           
               
               
           
         
       
       wherein X 1  is oxygen or sulfur; A is —X 2 —R 3  or —R 3  where X 2  is oxygen or sulfur and R 3  is a hydrocarbyl group; R 1  and R 2  are each independently hydrogen, a hydrocarbon group, an alkoxy group, or linked together to form a hydrocarbyl ring; and wherein R 4  and R 5  are each independently: hydrogen; a hydrocarbyl group; linked together to form a hydrocarbyl ring; —CH 2 CH 2 CN;
 —CH 2 CH 2 C(O)X 2 R 6  where R 6  is hydrogen or a hydrocarbyl group; or 
 [CH 2 CHR 7 O] y —Z where R 7  is alkyl, y is from 0 to 50, and Z is hydrogen or a hydrocarbyl group; with the proviso that at least one of R 4  and R 5  is not hydrogen. 
 
     
     
         2 . The composition of  claim 1  wherein (a), the oil of lubricating viscosity, has at least one property selected from the group consisting of: (i) a phosphorus content below 0.2% by weight, (ii) a sulfur content below 1% by weight, and (iii) a sulfated ash content below 1.5% by weight. 
     
     
         3 . The composition of  claim 1  wherein (b) is represented by formula (II) 
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  are each independently hydrogen, a hydrocarbon group, an alkoxy group, or linked together form a hydrocarbyl ring; R 3  is hydrogen or a hydrocarbon group; R 4  and R 5  are each independently hydrogen, a hydrocarbyl group, or linked together to form a hydrocarbyl ring, with the proviso that at least one of R 4  and R 5  is not hydrogen. 
     
     
         4 . The composition of  claim 1  wherein (b) is represented by formula (III) 
       
         
           
           
               
               
           
         
       
       wherein X 1  is oxygen or sulfur; A is —X 2 —R 3  or —R 3  where X 2  is oxygen or sulfur and R 3  is a hydrocarbyl group; and R 4  and R 5  are each independently hydrogen, a hydrocarbyl group, linked together to form a hydrocarbyl ring, with the proviso that at least one of R 4  and R 5  is not hydrogen. 
     
     
         5 . The composition of  claim 1  wherein the addition of (b), the additive component, boosts the TBN of overall composition by at least 1 mg KOH/g; and
 wherein the sulfated ash content of the composition is less than or equal to 1.0% by weight. 
 
     
     
         6 . The composition of  claim 1  wherein R 3  is: (i) a hydrocarbyl group containing at least 10 carbon atoms; (ii) a hydrocarbyl group containing at least one branch point; (iii) a fully saturated alkyl group; or (iv) combinations thereof. 
     
     
         7 . The composition of  claim 1  wherein: (i) the nitrogen content of the composition is less than 0.4 percent by weight, (ii) the soap content of the composition is less than 5 percent by weight, or (iii) combinations thereof. 
     
     
         8 . The composition of  claim 1  wherein component (b) is derived from a 4-(dialkylamino)benzoic acid and an alcohol, optionally in the presence of a catalyst. 
     
     
         9 . The composition of  claim 1  wherein component (b) is derived from an alcohol component comprising a mixture of linear alcohols containing 1 to 4 carbon atoms, a mixture of linear alcohols containing 2 to 10 carbon atoms, a mixture of linear alcohols containing 3 to 6 carbon atoms, a mixture of linear alcohols containing 8 to 10 carbon atoms, decyl alcohol, isotridecyl alcohol, 2-ethylhexanol, or combinations thereof. 
     
     
         10 . The composition of  claim 1  further comprising at least one additive selected from the group consisting of non-phosphorus-containing anti-wear agents, ashless dispersants, antioxidants, friction modifiers, zinc dithiophosphates, dispersant viscosity modifiers and corrosion inhibitors. 
     
     
         11 . A method for preparing a lubricating composition comprising combining the components set forth in  claim 1 . 
     
     
         12 . A method of lubricating an internal combustion engine, comprising supplying to said engine a lubricating composition comprising (a) an oil of lubricating viscosity and (b) an additive of formula (I) 
       
         
           
           
               
               
           
         
       
       wherein X 1  is oxygen or sulfur; A is —X 2 —R 3  or —R 3  where X 2  is oxygen or sulfur and R 3  is a hydrocarbyl group; R 1  and R 2  are each independently hydrogen, a hydrocarbon group, an alkoxy group, or linked together to form a hydrocarbyl ring; and wherein R 4  and R 5  are each independently: hydrogen; a hydrocarbyl group; a hydrocarbyl group linked together to form a hydrocarbyl ring; —CH 2 CH 2 CN;
 —CH 2 CH 2 C(O)X 2 R 6  where R 6  is hydrogen or a hydrocarbyl group; or 
 —[CH 2 CHR 7 O] y —Z where R 7  is alkyl, y is from 0 to 50, and Z is hydrogen or a hydrocarbyl group; with the proviso that at least one of R 4  and R 5  is not hydrogen.