Functionalized Copolymers And Lubricating Compositions Thereof

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.

1 . A lubricating composition comprising an oil of lubricating viscosity and a (thio)phosphate salt of an amine-functionalized esterified copolymer, wherein the esterified copolymer comprises units derived from monomers:
 (i) an α-olefin and   (ii) an ethylenically unsaturated carboxylic acid or derivative thereof, esterified with at least one alcohol, and wherein at least a portion of carboxylic acid groups are reacted with at least one amine.   
     
     
         2 . The lubricating composition of  claim 1 , wherein the α-olefin is a linear or branched olefin, or mixtures thereof. 
     
     
         3 . The lubricating composition of  claim 2 , wherein the α-olefin includes 1-decene, 1-undecene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene 1-octadecene, or mixtures thereof. 
     
     
         4 . The lubricating composition of  claim 3 , wherein the α-olefin is 1-dodecene. 
     
     
         5 . The lubricating composition of  claim 1 , wherein the ethylenically unsaturated carboxylic acid or derivative thereof includes itaconic anhydride, maleic anhydride, methyl maleic anhydride, ethyl maleic anhydride, dimethyl maleic anhydride or mixtures thereof. 
     
     
         6 . The lubricating composition of  claim 1 , wherein the ethylenically unsaturated carboxylic acid or derivative thereof is maleic anhydride or a derivative thereof. 
     
     
         7 . The lubricating composition of  claim 1 , wherein the α-olefin is 1-dodecene and the unsaturated carboxylic acid or derivative thereof is maleic anhydride. 
     
     
         8 . The lubricating composition of  claim 1 , wherein the copolymer has, prior to esterification, a reduced specific viscosity of up to 0.08. 
     
     
         9 . The lubricating composition of  claim 1 , wherein the alcohol is a linear or branched alcohol, a cyclic or acyclic alcohol, or a combination of features thereof. 
     
     
         10 . The lubricating composition of  claim 1 , wherein the alcohol comprises a primary alcohol branched at the β- or higher position and may have at least 12 (or at least 16, or at least 18 or at least 20) carbon atoms. 
     
     
         11 . The lubricating composition of  claim 1 , wherein the alcohol comprises a mixture of (i) a Guerbet alcohol and (ii) a linear alcohol containing 6 to 20, or 8 to 18, or 10 to 15 carbon atoms other than a Guerbet alcohol. 
     
     
         12 . The lubricating composition of  claim 1 , wherein the amine is capable of providing a TBN (i.e., a total base number) of greater than 0 mg KOH/g. 
     
     
         13 . The lubricating composition of  claim 12 , wherein the amine includes an amino-hydrocarbyl morpholine (such as n-aminopropylmorpholine), an aminoalcohol, vinyl pyridine, N-vinyl imidazole, a dialkylaminoalkyl (meth)acrylamide or dialkylaminoalkyl (meth)acrylate, a N-substituted alkanediamine, or mixtures thereof. 
     
     
         14 . The lubricating composition of  claim 13 , wherein the amino alcohol includes at least one of dimethylethanolamine, ethanolamine, isopropanolamine, diethanolamine, triethanolamine, N,N-diethylethanolamine, N,N-dibutylethanolamine, 3-amino-1,2-propanediol, serinol, 2-amino-2-methyl-1,3-propanediol, tris(hydroxymethyl)-aminomethane, diisopropanolamine, N-methyldiethanolamine, 3-(dimethylamino)-2,2-dimethylpropan-1-ol, and 2-(2-aminoethylamino)ethanol. 
     
     
         15 . The lubricating composition of  claim 1 , wherein the (thio)phosphate salt is derivable from a (thio)phosphating agent or (thio)phosphorylating agent which may have phosphorus in its +5 oxidation state. 
     
     
         16 . The lubricating composition of  claim 15 , wherein the (thio)phosphorylating agent comprises at least one of POCl 3 , P 2 O 5 , P 4 O 10 , polyphosphoric acid, P 2 S 5 , P 4 S 10 , phosphoric acid, thiophosphoric acid, or mixtures thereof. 
     
     
         17 . The lubricating composition of  claim 15 , wherein the (thio)phosphate salt is a product obtained/obtainable by reacting: the esterified copolymer with a (thio)phosphate, wherein the (thio)phosphate is obtained/obtainable by reacting a hydroxy-containing carboxylic compound (typically a hydroxy-containing carboxylic acid, or derivatives thereof), a (typically sulphur-free) phosphating agent, and optionally an alcohol. 
     
     
         18 . A method of lubricating a mechanical device comprising supplying to the device a lubricating composition of any preceding  claim 1 . 
     
     
         19 . The method of  claim 18 , wherein the mechanical device is a driveline device, such as a manual transmission. 
     
     
         20 . The method of  claim 18 , wherein the mechanical device comprises at least one of a planetary hub reduction axle, a mechanical steering and transfer gear box in a utility vehicle, a synchromesh gear box, a power take-off gear, a limited slip axle, and a planetary hub reduction gear box.