Polyester Quaternary Ammonium Salts

Abstract

The invention relates to polyester quaternary ammonium salts, including amine, amide, and ester salts, processes for making them, and their use as additives, including their use in fuels, such as diesel fuel and fuel oils. The invention particularly relates to the use of polyester quaternary ammonium salts as detergents in fuels and the methods of making them.

What is claimed is: 
     
         1 . A composition comprising a quaternized polyester salt which comprises the reaction product of:
 a. a polyester containing a tertiary amino group; and   b. quaternizing agent suitable for converting the tertiary amino group to a quaternary nitrogen.   
     
     
         2 . The composition of  claim 1  wherein the polyester comprises the reaction product of a fatty carboxylic acid containing at least one hydroxyl group and a compound having an oxygen or nitrogen atom capable of condensing with said acid where said compound contains a tertiary amino group. 
     
     
         3 . The composition of  claim 2  wherein the fatty carboxylic acid is represented by the formula: 
       
         
           
           
               
               
           
         
       
       where R 1  is a hydrogen or a hydrocarbyl group containing from 1 to 20 carbon atoms and R 2  is a hydrocarbylene group containing from 1 to 20 carbon atoms; and
 wherein the compound having an oxygen or nitrogen atom capable of condensing with said acid and further having a tertiary amino group is represented by the formula: 
 
       
         
           
           
               
               
           
         
       
       where R 3  is a hydrocarbyl group containing from 1 to 10 carbon atoms; R 4  is a hydrocarbyl group containing from 1 to 10 carbon atoms; R 5  is a hydrocarbylene group containing from 1 to 20 carbon atoms; and X 1  is O or NR 6  where R 6  is a hydrogen or a hydrocarbyl group containing from 1 to 10 carbon atoms; 
     
     
         4 . The composition of  claim 1  wherein the quaternized polyester salt comprises a quaternized polyester amide salt wherein the polyester containing a tertiary amino group used to prepare said quaternized polyester salt comprises a polyester amide containing a tertiary amino group. 
     
     
         5 . The composition of  claim 1  wherein the quaternized polyester salt comprises a cation represented by the following formula: 
       
         
           
           
               
               
           
         
       
       where R 1  is a hydrogen or a hydrocarbyl group containing from 1 to 20 carbon atoms and R 2  is a hydrocarbylene group containing from 1 to 20 carbon atoms; R 3  is a hydrocarbyl group containing from 1 to 10 carbon atoms; R 4  is a hydrocarbyl group containing from 1 to 10 carbon atoms; R 5  is a hydrocarbylene group containing from 1 to 20 carbon atoms; R 6  is a hydrogen or a hydrocarbyl group containing from 1 to 10 carbon atoms; n is a number from 1 to 10; R 7  is hydrogen, a hydrocarbonyl group containing from 1 to 22 carbon atoms, or a hydrocarbyl group containing from 1 to 22 carbon atoms; and X 2  is a group derived from the quaternizing agent. 
     
     
         6 . The composition of  claim 2  wherein the compound having an oxygen or nitrogen atom capable of condensing with said acid and further having a tertiary amino group comprises N,N-diethylethylenediamine, N,N-dimethylethylenediamine, N,N-dibutylethylenediamine, N,N-dimethyl-1,3-diaminopropane, N,N-diethyl-1,3-diaminopropane, N,N-dimethylaminoethanol, N,N-diethylaminoethanol, or combinations thereof. 
     
     
         7 . The composition of  claim 2  wherein the fatty carboxylic acid containing at least one hydroxyl group comprises: 12-hydroxystearic acid; ricinoleic acid; 12-hydroxy dodecanoic acid; 5-hydroxy dodecanoic acid; 5-hydroxy decanoic acid; 4-hydroxy decanoic acid; 10-hydroxy undecanoic acid; or combinations thereof. 
     
     
         8 . The composition of  claim 1  wherein the quaternizing agent comprises ethylene oxide, propylene oxide, butylene oxide, styrene oxide, or combinations thereof wherein the quaternizing agent is used in combination with an acid. 
     
     
         9 . The composition of  claim 1  further comprising a metal deactivator, a detergent other than those of  claim 1 , a dispersant, a viscosity modifier, a friction modifier, a dispersant viscosity modifier, an extreme pressure agent, an antiwear agent, an antioxidant, a corrosion inhibitor, a foam inhibitor, a demulsifier, a pour point depressant, a seal swelling agent, a wax control polymer, a scale inhibitor, a gas-hydrate inhibitor, or combinations thereof. 
     
     
         10 . The composition of  claim 1  further comprising an overbased metal containing detergent, a zinc dialkyldithiophosphate, or combinations thereof. 
     
     
         11 . The composition of  claim 1 , further comprising a fuel which is liquid at room temperature. 
     
     
         12 . The method of fueling an internal combustion engine comprising:
 A. supplying to said engine:
 i. a fuel which is liquid at room temperature; and 
 ii. a composition comprising a quaternized polyester salt which comprises the reaction product of: (a) a polyester containing a tertiary amino group; and (b) quaternizing agent suitable for converting the tertiary amino group to a quaternary nitrogen. 
   
     
     
         13 . A process of making a quaternary ammonium salt detergent comprising:
 I. reacting (a) a polyester containing a tertiary amino group; and (b) quaternizing agent suitable for converting the tertiary amino group to a quaternary nitrogen;   thereby obtaining the quaternized dispersant.   
     
     
         14 . The process of  claim 14  wherein the polyester containing a tertiary amino group is prepared by a process comprising:
 I. reacting (a)(i) a fatty carboxylic acid containing at least one hydroxyl group and (a)(ii) a compound having an oxygen or nitrogen atom capable of condensing with said acid and further having a tertiary amino group; 
 thereby obtaining the polyester containing a tertiary amino group.