Imidazole containing quaternary ammonium salts

Abstract

The present technology is related to imidazole containing quaternary ammonium salts and the use of such quaternary ammonium salts in compositions to improve the water shedding performance of the compositions.

1 . A composition comprising an imidazole containing quaternary ammonium salt (“imidazole quat”), wherein the imidazole 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 tertiary amino group containing imidazole compound of formula: 
 
 
       
         
           
           
               
               
           
         
         
           
             wherein R is an amine or alkanol capable of condensing with said hydrocarbyl-substituted acylating agent and having from 3 to 8 carbon atoms; and 
           
         
         b) a quaternizing agent suitable for converting the quaternizable amino group of the nitrogen containing compound to a quaternary nitrogen. 
       
     
     
         2 . The composition of  claim 1 , wherein the hydrocarbyl-substituted acylating agent comprises at least one polyisobutenyl succinic anhydride or polyisobutenyl succinic acid. 
     
     
         3 . The composition of  claim 1 , wherein the reaction in a) is carried out at a temperature of greater than 80, or 90, or 100° C. 
     
     
         4 . The composition of  claim 1 , wherein the reaction in a) is carried out at a temperature of less than 80° C. 
     
     
         5 . The composition of  claim 1 , wherein the quaternizing agent comprises at least one dialkyl sulfate, alkyl halide, hydrocarbyl substituted carbonate, hydrocarbyl epoxide, carboxylate, alkyl ester or mixtures thereof. 
     
     
         6 . The composition of  claim 5 , wherein the quaternizing agent is a hydrocarbyl epoxide. 
     
     
         7 . The composition of  claim 6 , wherein the quaternizing agent comprises a C 4  to C 14  epoxide. 
     
     
         8 . The composition of  claim 7 , 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 8 , wherein the quaternizing agent is epoxyhexadecane. 
     
     
         11 . The composition of  claim 8 , wherein the quaternizing agent comprises butylene oxide. 
     
     
         12 . The composition of  claim 6  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 5  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 6 , wherein the quaternizing agent is an oxalate or terephthalate. 
     
     
         17 . The composition of  claim 1 , further comprising at least one other additive. 
     
     
         18 . The composition of  claim 17 , 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. 
     
     
         19 . The composition of  claim 18 , wherein the at least one other additive comprises at least one hydrocarbyl-substituted succinic acid. 
     
     
         20 . The composition of  claim 18 , wherein the at least one other additive comprises at least one hydrocarbyl-substituted quaternary ammonium salt. 
     
     
         21 . The composition of  claim 18 , 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. 
     
     
         22 . The composition of  claim 19 , wherein the hydrocarbyl-substituent is a polyisobutylene having a molecular weight ranging from 100 to 5000. 
     
     
         23 . The composition of  claim 18 , wherein the at least one other additive comprises at least one Mannich compound. 
     
     
         24 . The composition of  claim 1 , further comprising a fuel that is liquid at room temperature. 
     
     
         25 . The composition of  claim 24 , wherein the fuel is gasoline or diesel. 
     
     
         26 . The fuel composition of  claim 24  further comprising at least one of a low number average molecular weight soap, a low number average molecular weight polyisobutylene succinimide (PIBSI), or a mixture thereof. 
     
     
         27 . The fuel composition of  claim 24 , further comprising a low number average molecular weight soap with a number average molecular weight (M n ) of less than 340. 
     
     
         28 . The fuel composition of  claim 24 , further comprising from 0.01 to 25 ppm of a metal and from 1 to 12 ppm of a corrosion inhibitor. 
     
     
         29 . The fuel composition of  claim 28 , wherein the corrosion inhibitor is an alkenyl succinic acid comprising at least one of dodecenyl succinic acid (DDSA), hexadecenyl succinic acid (HDSA), or mixtures thereof. 
     
     
         30 . The fuel composition of  claim 24 , wherein the fuel comprises PIBSI with a low number average molecular weight M n  of less than 400. 
     
     
         31 . A method of improving water shedding performance of a fuel composition comprising adding a composition comprising an imidazole quat according to  claims 1  to said fuel. 
     
     
         32 . The composition of  claim 1 , further comprising an oil of lubricating viscosity. 
     
     
         33 . A method of operating an internal combustion engine comprising:
 c) supplying to said engine:
 a fuel, wherein said fuel
 1. is liquid at room temperature; and 
 2. has a composition comprising an imidazole quat according to  claim 1  therein; and 
 
   d) operating said engine.   
     
     
         34 . A method of operating an internal combustion engine comprising:
 e) supplying to a crankcase of said engine:
 an oil of lubricating viscosity having a composition comprising an imidazole quat according to  claim 1  therein, and 
   f) operating said engine.   
     
     
         35 . The method of  claim 34  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 %. 
     
     
         36 . A method of reducing and/or preventing injector deposits comprising:
 g) supplying to a fuel injector of said engine:
 a fuel, wherein said fuel
 1. is liquid at room temperature; and 
 2. has a composition comprising an imidazole quat according to  claim 1  therein; and 
 
   h) operating said engine.   
     
     
         37 . The method of  claim 36 , wherein the deposits comprise a low number average molecular weight soap, a low number average molecular weight polyisobutylene succinimide (PIBSI), or mixtures thereof. 
     
     
         38 . The method of  claim 37  wherein the fuel comprises a low number average molecular weight soap with a number average molecular weight (M n ) of less than 340. 
     
     
         39 . The method of  claim 36  wherein the fuel comprises from 0.01 to 25 ppm of a metal and from 1 to 12 ppm of a corrosion inhibitor. 
     
     
         40 . The method of  claim 39  wherein the corrosion inhibitor is an alkenyl succinic acid comprising at least one of dodecenyl succinic acid (DDSA), hexadecenyl succinic acid (HDSA), or mixtures thereof. 
     
     
         41 . The method of  claim 37 , wherein the fuel comprises a PIBSI with a low number average molecular weight M n  of less than 400. 
     
     
         42 . The method of  claim 36 , wherein the fuel is gasoline or diesel. 
     
     
         43 . The method of  claim 36 , wherein the engine comprises a high pressure common rail injector system. 
     
     
         44 . (canceled) 
     
     
         45 . (canceled) 
     
     
         46 . (canceled)