Epoxide quaternized quaternary ammonium salts

Abstract

The present technology is related to quaternary ammonium salts prepared with alcohol functionalized and/or C 4 to C 20 epoxide quaternizing agents, such as, for example, glycidol and 1,2-butylene oxide, and the use of such quaternary ammonium salts in fuel compositions to improve the water shedding performance of the fuel composition.

1 . A composition comprising at least one hydrocarbyl-substituted succinic acid wherein the hydrocarbyl-substituent is a polyisobutylene having a number average molecular weight ranging from 100 to 5000 and an epoxide quaternary ammonium salt (“epoxide quat”), wherein the epoxide quat comprises the reaction product of:
 a. a quaternizable compound that is the reaction product of:
 (i) a hydrocarbyl-substituted acylating agent, wherein the hydrocarbyl-substituent has a number average molecular weight ranging from 100 to 5000, and 
 (ii) a nitrogen containing compound having an oxygen or nitrogen atom capable of reacting with said hydrocarbyl-substituted acylating agent, and further having at least one quaternizable amino group; and 
 
 b. a quaternizing agent comprising alcohol functionalized epoxides; C 4  to C 20  epoxides; and mixtures thereof. 
 
     
     
         2 . The composition of  claim 1 , wherein the hydrocarbyl-substituent of said acylating agent has a number average molecular weight of 550. 
     
     
         3 . The composition of  claim 1 , wherein the quaternizable amino group is a primary, secondary or tertiary amino group. 
     
     
         4 . The composition of  claim 1 , wherein the hydrocarbyl-substituted acylating agent comprises at least one polyisobutenyl succinic anhydride or polyisobutenyl succinic acid. 
     
     
         5 . The composition of  claim 1 , wherein the reaction in a) is carried out at a temperature of greater than 80, 90, or 100° C. 
     
     
         6 . The composition of  claim 1 , wherein the reaction in a) is carried out at a temperature of less than 80° C. 
     
     
         7 . The composition of  claim 1 , wherein the quaternizing agent comprises a C 4  to C 14  epoxide. 
     
     
         8 . The composition of  claim 1 , wherein the quaternizing agent comprises an alcohol functionalized epoxide. 
     
     
         9 . The composition of  claim 8 , wherein the quaternizing agent is glycidol. 
     
     
         10 . The composition of  claim 7 , wherein the quaternizing agent is 1,2-epoxyhexadecane. 
     
     
         11 . The composition of  claim 7 , wherein the quaternizing agent comprises butylene oxide. 
     
     
         12 . The composition of  claim 1 , wherein the quaternizing agent is employed in the presence of a protic solvent. 
     
     
         13 . The composition of  claim 12 , wherein the protic solvent comprises 2-ethylhexanol, water, and mixtures thereof. 
     
     
         14 . The composition of  claim 1 , wherein the quaternizing agent is employed in the presence of an acid. 
     
     
         15 . The composition of  claim 14 , wherein the acid is present in the structure of the acylating agent. 
     
     
         16 . The composition of  claim 1 , further comprising at least one other additive. 
     
     
         17 . The composition of  claim 16 , wherein the at least one other additive comprises a detergent, a dispersant, a demulsifier, a lubricity agent, a cold flow improver, an antioxidant, or a mixture thereof. 
     
     
         18 . The composition of  claim 16 , wherein the at least one other additive comprises at least one hydrocarbyl-substituted quaternary ammonium salt. 
     
     
         19 . The composition of  claim 16 , wherein the at least one other additive comprises at least one detergent/dispersant that is an amphiphilic substance which possess at least one hydrophobic hydrocarbon radical with a number average molecular weight of 100 to 10000 and at least one polar moiety selected from (i) Mono- or polyamino groups having up to 6 nitrogen atoms, at least one nitrogen atom having basic properties; (ii) Hydroxyl groups in combination with mono or polyamino groups, at least one nitrogen atoms having basic properties; (v) Polyoxy-C 2  to C 4  alkylene moieties terminated by hydroxyl groups, mono- or polyamino groups, at least one nitrogen atom having basic properties, or by carbamate groups; (vii) Moieties derived from succinic anhydride and having hydroxyl and/or amino and/or amido and/or imido groups; and/or (viii) Moieties obtained by Mannich reaction of substituted phenols with aldehydes and mono- or polyamines. 
     
     
         20 . The composition of  claim 18 , wherein the hydrocarbyl-substituent is a polyisobutylene having a number average molecular weight ranging from 100 to 5000. 
     
     
         21 . The composition of  claim 16 , wherein the at least one other additive comprises at least one Mannich compound. 
     
     
         22 . The composition of  claim 1 , further comprising a fuel that is liquid at room temperature. 
     
     
         23 . The composition of  claim 22 , wherein the fuel is gasoline or diesel. 
     
     
         24 . The composition of  claim 1  further comprising an oil of lubricating viscosity. 
     
     
         25 . A method of operating an internal combustion engine comprising:
 a. supplying to said engine:
 (i) a fuel, wherein said fuel
 1. is liquid at room temperature; and 
 2. has a composition comprising an epoxide quat according to  claim 1  therein; and 
 
   b. operating said engine.   
     
     
         26 . A method of operating an internal combustion engine comprising:
 a. supplying to a crankcase of said engine:
 (i) an oil of lubricating viscosity; having a composition comprising an epoxide quat according to  claim 1  therein, and 
   b. operating said engine.   
     
     
         27 . The method of  claim 26  wherein the oil of lubricating viscosity has total sulfated ash of less than 1 wt % and/or a phosphorus content of less than 0.11 wt %. 
     
     
         28 . A method of improving water shedding performance of a fuel composition comprising adding a composition comprising an epoxide quat according to  claim 1  to said fuel composition. 
     
     
         29 . A method of reducing and/or preventing injector deposits comprising:
 c. supplying to a fuel injector of said engine:
 (i) a fuel, wherein said fuel
 1. is liquid at room temperature; and 
 2. has a composition comprising an epoxide quat according to  claim 1  therein; and 
 
   b. operating said engine.