Low molecular weight amide/ester containing quaternary ammonium salts

Abstract

The present technology is related to amide or ester containing quaternary ammonium salts having a hydrocarbyl substituent of number average molecular weight ranging from 300 to 750, and the use of such quaternary ammonium salts in fuel compositions to improve the water shedding performance of the fuel composition.

What we claim: 
     
         1 . A composition comprising an ester or amide containing quaternary ammonium salt (“amide/ester quat”), wherein the amide/ester 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 300 to 750, and 
 (ii) a nitrogen containing compound having an oxygen or nitrogen atom capable of reacting with said hydrocarbyl-substituted acylating agent to form an ester or amide, and further having at least one quaternizable amino group; 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 quaternizable amino group is a primary, secondary or tertiary amino group. 
     
     
         3 . The composition of any previous claim, wherein the hydrocarbyl-substituted acylating agent comprises at least one polyisobutenyl succinic anhydride or polyisobutenyl succinic acid. 
     
     
         4 . The composition of any previous claim, wherein the reaction of a)(i) with a)(ii) is carried out at a temperature of less than 80° C. 
     
     
         5 . The composition of any previous claim wherein the nitrogen containing compound excludes dimethylaminopropylamine. 
     
     
         6 . The composition of any previous claim, wherein the quaternizing agent comprises at least one dialkyl sulfate, alkyl halide, hydrocarbyl substituted carbonate, hydrocarbyl epoxide, carboxylate, alkyl ester, or mixtures thereof. 
     
     
         7 . The composition of  claim 6 , wherein the quaternizing agent is a hydrocarbyl epoxide. 
     
     
         8 . The composition of  claim 7 , wherein the quaternizing agent is a hydrocarbyl epoxide in combination with an acid. 
     
     
         9 . The composition of  claim 6 , wherein the quaternizing agent is an oxalate or terephthalate. 
     
     
         10 . The composition of any previous claim wherein the quaternizing agent excludes methyl salicylate. 
     
     
         11 . The composition of any previous claim, further comprising at least one other additive. 
     
     
         12 . The composition of  claim 11 , 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. 
     
     
         13 . The composition of  claim 11 , wherein the at least one other additive comprises at least one hydrocarbyl-substituted succinic acid. 
     
     
         14 . The composition of  claim 11 , wherein the at least one other additive comprises at least one hydrocarbyl-substituted quaternary ammonium salt. 
     
     
         15 . The composition of  claim 11 , 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. 
     
     
         16 . The composition of  claims 13  through  15 , wherein the hydrocarbyl-substituent is a polyisobutylene having a molecular weight ranging from 100 to 5000. 
     
     
         17 . The composition of  claim 11 , wherein the at least one other additive comprises at least one Mannich compound. 
     
     
         18 . The composition of any previous claim, further comprising a fuel that is liquid at room temperature. 
     
     
         19 . The composition of  claim 18 , wherein the fuel is gasoline or diesel. 
     
     
         20 . The fuel composition of  claim 18  or  19  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. 
     
     
         21 . The fuel composition of  claims 18  through  20 , further comprising a low number average molecular weight soap with a number average molecular weight (M n ) of less than 340. 
     
     
         22 . The fuel composition of  claims 18  through  20 , further comprising from 0.01 to 25 ppm of a metal and from 1 to 12 ppm of a corrosion inhibitor. 
     
     
         23 . The fuel composition of  claim 22 , 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. 
     
     
         24 . The fuel composition of  claims 18  through  20 , wherein the fuel comprises PIBSI with a low number average molecular weight M n  of less than 400. 
     
     
         25 . A method of improving water shedding performance of a fuel composition comprising employing a composition comprising an amide/ester quat according to any  claims 1  to  24 . 
     
     
         26 . The composition of any of  claims 1  to  17 , further comprising an oil of lubricating viscosity. 
     
     
         27 . 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 amide/ester quat according to any  claims 1  to  17  therein; and 
 
   b) operating said engine.   
     
     
         28 . 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 amide/ester quat according to any  claims 1  to  17  therein, and 
   b) operating said engine.   
     
     
         29 . The method of  claim 28  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 %. 
     
     
         30 . A method of reducing and/or preventing injector deposits comprising:
 a) 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 amide/ester quat according to any  claims 1  to  17  therein; and 
 
   b) operating said engine.   
     
     
         31 . The method of  claim 30 , wherein the deposits comprise a low number average molecular weight soap, a low number average molecular weight polyisobutylene succinimide (PIBSI), or mixtures thereof. 
     
     
         32 . The method of  claim 31  wherein the fuel comprises a low number average molecular weight soap with a number average molecular weight (M n ) of less than 340. 
     
     
         33 . The method of  claims 30  through  32  wherein the fuel comprises from 0.01 to 25 ppm of a metal and from 1 to 12 ppm of a corrosion inhibitor. 
     
     
         34 . The method of  claim 33  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. 
     
     
         35 . The method of  claim 30 , wherein the fuel comprises a PIBSI with a low number average molecular weight M n  of less than 400. 
     
     
         36 . The method of  claims 30  to  36 , wherein the fuel is gasoline or diesel. 
     
     
         37 . The method of any of  claims 27  to  35  wherein the engine comprises a high pressure common rail injector system. 
     
     
         38 . The use of composition of any of  claims 1  to  17  to reduce and/or prevent internal deposits in an engine operated with a fuel, wherein the fuel is gasoline or diesel. 
     
     
         39 . The use of  claim 38  wherein the engine comprises a high pressure common rail injector system. 
     
     
         40 . The use of  claim 38  or  39  wherein said deposits are internal diesel injector deposits (IDID) deposits.