Ultra-low molecular weight amide/ester containing quaternary ammonium salts having short hydrocarbon tails

Abstract

The present technology is related to amide or ester containing quaternary ammonium salts having a hydrocarbyl substituent of number average molecular weight less 300, and additive packages having such quaternary ammonium salts and improved stability.

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 less than 300, 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  claim 1 , wherein the hydrocarbyl-substituted acylating agent comprises at least one dodecenyl succinic anhydride, dodecenyl succinic acid, hexadecenyl succinic anhydride, hexadecenyl succinic acid, octadecenyl succinic anhydride, octadecenyl succinic acid, or mixtures thereof. 
     
     
         4 - 5 . (canceled) 
     
     
         6 . 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. 
     
     
         7 - 17 . (canceled) 
     
     
         18 . The composition of  claim 1 , further comprising a hydrolyzed alkenyl succinic acid or anhydride with a molecular weight M n  ranging from about 225 to about 1000. 
     
     
         19 . The composition of  claim 18 , wherein the hydrolyzed alkenyl succinic acid or anhydride has a M n  of 1000. 
     
     
         20 . The composition of  claim 19 , wherein the hydrolyzed alkenyl succinic acid or anhydride has a M n  of 550. 
     
     
         21 . A composition comprising an ester or amide containing quaternary ammonium salt (“amide/ester quat”) and a hydrolyzed alkenyl succinic acid or anhydride with a molecular weight M n  ranging from about 225 to about 1000, wherein the amide/ester quat comprises the reaction product of:
 c) 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 less 100 to 700, 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 
 
 d) a quaternizing agent suitable for converting the quaternizable amino group of the nitrogen containing compound to a quaternary nitrogen. 
 
     
     
         22 . The composition of  claim 21 , further comprising a fuel that is liquid at room temperature. 
     
     
         23 . (canceled) 
     
     
         24 . The composition of  claim 22  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. 
     
     
         25 . The composition of  claim 24 , wherein said low number average molecular weight soap has a number average molecular weight (M n ) of less than 340. 
     
     
         26 . The composition of  claim 22 , further comprising from 0.01 to 25 ppm of a metal and from 1 to 12 ppm of a corrosion inhibitor. 
     
     
         27 . The composition of  claim 26 , 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. 
     
     
         28 . The composition of  claim 24 , wherein said low number average molecular weight PIBSI has an M n  of less than 400. 
     
     
         29 - 32 . (canceled) 
     
     
         33 . A method of reducing and/or preventing injector deposits comprising:
 e) 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  claim 1  therein; and 
 
   f) operating said engine.   
     
     
         34 . The method of  claim 33 , wherein the fuel comprises a low number average molecular weight soap, a low number average molecular weight polyisobutylene succinimide (PIBSI), or mixtures thereof. 
     
     
         35 . The method of  claim 34  wherein said low number average molecular weight soap has a number average molecular weight (M n ) of less than 340. 
     
     
         36 . The method of  claim 33  wherein the fuel comprises from 0.01 to 25 ppm of a metal and from 1 to 12 ppm of a corrosion inhibitor. 
     
     
         37 . The method of  claim 36  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. 
     
     
         38 . The method of  claim 34 , wherein said low number average molecular weight PIBSI has an M n  of less than 400. 
     
     
         39 - 46 . (canceled)