Power transmission fluids with enhanced antishudder durability and handling characteristics

Abstract

A finished power transmitting fluid having enhanced friction durability and improved μ/v characteristics on paper, steel and advanced friction materials such as carbon fiber, and which may provide a lubricant composition that carries minimal concern for skin sensitization and related health, safety, and environmental issues, can contain lubricating base oil, a friction modifier produced by reacting a polyamine with an aliphatic mono acid such as oleic or isostearic acid under conditions to form a mixture of 1,2-disubstituted imidazoline containing components, wherein further acylation of residual active nitrogens with mono or diacids or anhydrides affords friction modifier compositions having enhanced frictional and handling characteristics.

1 . A fluid composition, comprising: 
 (1) a major amount of a base oil, and    (2) a minor amount of an additive comprising:    (i) a reaction product of an aliphatic carboxylic acid and a polyamine obtained under conditions sufficient to produce a mixture containing one or more compounds represented by formula I and/or II; (ii) a reaction product obtained by (a) reacting an aliphatic carboxylic acid and a polyamine under conditions sufficient to produce a mixture of 1,2-disubstituted imidazolines containing one or more compounds represented by formula I and/or II, and then (b) treating under conditions to produce a further mixture containing one or more compounds represented by formula III, IV, V and/or VI; or (iii) a mixture containing at least one compound represented by formula I and/or II and at least one compound from among the compounds represented by formulas III to VI, wherein said formulas are:                          wherein R 1  and R 2  are independent of one another and represent C 3  to C 30  straight or branched alkyl, alkenyl or aryl or heteroatom derivatives thereof, such as an alkyl having heteroatoms, as one example; R 3  and R 4  are independent of one another and are selected from the group consisting of H, —OH, —OR, —COOH, —SH, —SR, straight chain, branched alkyl, alkenyl radicals and hydrocarbyl groups in oligomeric or polymeric form that are derived from propylene, isobutylene and higher olefins having terminal, internal and vinylidene double bonds, R represents an alkyl or alkenyl group having up to 30 carbon atoms in linear, branched or cyclic form and n is a value from 0 to 5.    
     
     
         2 . The fluid composition of  claim 1 , wherein the additive contains a compound represented by formula I and a compound represented by formula II.  
     
     
         3 . The fluid composition of  claim 1 , wherein the additive contains a compound represented by formula I, a compound represented by formula II, and a compound represented by formula III and a compound represented by formula IV.  
     
     
         4 . The fluid composition of  claim 1;  wherein the additive contains a compound represented by formula I, a compound represented by formula II, a compound represented by formula V and a compound represented by formula VI.  
     
     
         5 . The fluid composition of  claim 1 , wherein the additive contains a compound represented by formula III and a compound represented by formula IV.  
     
     
         6 . The fluid composition of  claim 1 , wherein the additive contains a compound represented by formula V and a compound represented by formula VI.  
     
     
         7 . The fluid composition of  claim 1 , wherein said additive comprises a mixture containing at least one compound represented by formula I or II and at least one compound from among the compounds represented by formulas III to VI.  
     
     
         8 . The fluid composition of  claim 1 , wherein the base oil comprises one or more of a natural oil, a mixture of natural oils, a synthetic oil, a mixture of synthetic oils, a mixture of natural and synthetic oils, and a base oil derived from a Fischer-Tropsch or gas-to-liquid process.  
     
     
         9 . The fluid composition of  claim 1 , wherein the base oil has a kinematic viscosity of from about 2 centistokes to about 10 centistokes at 100° C.  
     
     
         10 . The fluid composition of  claim 1 , wherein the fluid composition contains an ashless dispersant.  
     
     
         11 . The fluid according to  claim 1  or  10 , wherein said fluid composition contains at least one a detergent, another friction modifier, an antioxidant, an antiwear agent, an antifoam agent, a viscosity index improver, a copper corrosion inhibitor, an anti-rust additive, a seal swell agent, and/or a metal deactivator.  
     
     
         12 . The fluid composition of  claim 1 , wherein the additive is present in an amount of about 0.01 wt. % to about 10 wt. %, based on the fluid composition.  
     
     
         13 . The fluid composition of  claim 1 , wherein the additive is present in an amount of from 0.1 wt. % to 5.0 wt. %.  
     
     
         14 . A transmission containing the fluid composition of  claim 1 .  
     
     
         15 . The transmission of  claim 14 , wherein the transmission comprises a continuously variable transmission.  
     
     
         16 . The transmission of  claim 14 , wherein the transmission comprises a dual clutch transmission.  
     
     
         17 . The transmission of  claim 14 , wherein the transmission comprises an automatic transmission.  
     
     
         18 . The transmission of  claim 14 , wherein the transmission comprises a manual transmission.  
     
     
         19 . The fluid composition of  claim 1 , wherein the fluid is adapted for use in a transmission employing one or more of an electronically controlled converter clutch, a slipping torque converter, a lock-up torque converter, a starting clutch, and one or more shifting clutches.  
     
     
         20 . The fluid composition of  claim 1 , wherein the fluid is adapted for use in a belt, chain, or disk-type continuously variable transmission, a 4-, 5-, 6-, or 7-speed automatic transmission, a manual transmission, an automated manual transmission, or a dual clutch transmission.  
     
     
         21 . The fluid composition of  claim 1 , wherein the fluid is adapted for use in an industrial gear or an automotive gear.  
     
     
         22 . A vehicle comprising an engine and a transmission, the transmission including the fluid of  claim 1 .  
     
     
         23 . A vehicle comprising a differential, the differential including a lubricant containing the fluid composition of  claim 1 .  
     
     
         24 . A method for producing friction modifier compounds comprising: 
 (a) reacting a molar excess of at least one carboxylic acid R 1 COOH with a linear polyamine represented by the formula H 2 N—(CH 2 CH 2 NH) x —CH 2 , where x represents an integer of 1 to 10 at a temperature in a range of about 120° C. to about 180° C. for about 5 to about 20 hours, said compounds being represented by formula I and II                          wherein R 1  represents a C 3  to C 30  straight or branched alkyl, alkenyl or aryl or heteroatom derivative thereof, and n is a value from 0 to 5.    
     
     
         25 . A method for producing friction modifier compounds according to  claim 24 , wherein R 1  represents —C 17 H 35 .  
     
     
         26 . A method for producing friction modifier compounds according to  claim 24 , wherein said molar ratio of carboxylic acid to polyamine is about 1:1 to about 2:1.  
     
     
         27 . A method for producing friction modifier compounds according to  claim 26 , wherein said molar ratio is about 1.2:1 to about 1.6:1.  
     
     
         28 . A method for producing friction modifier compounds according to  claim 27 , wherein said molar ratio of carboxylic acid to polyamine is about 4:3.  
     
     
         29 . A method for producing friction modifier compounds according to  claim 24 , wherein the reaction is for about 12 to about 16 hours.  
     
     
         30 . A method for producing friction modifier compounds according to  claim 25 , wherein the reaction temperature is about 150° C.  
     
     
         31 . A method for producing friction modifier compounds according to  claim 24 , wherein said method yields a reaction product in which there is a ratio of at least one compound represented by formula I to at least one compound represented by formula II of about 2:1.  
     
     
         32 . A method for producing friction modifier compounds according to  claim 24 , wherein said method further comprises post treating the reaction products from (a) with at least one carboxylic acid R 2 COOH in an amount that at least a portion of the reactive nitrogen atoms in a compound of formula I or II can be acylated, whereby a compound(s) represented by formula III and a compound(s) represented by formula IV are obtained:  
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  are independent of one another and represent C 3  to C 30  straight or branched alkyl, alkenyl or aryl groups or a heteroatom derivative thereof.  
     
     
         33 . A method for producing friction modifier compounds according to  claim 24 , wherein said method further comprises post-treating a reaction product comprising at least one compound represented by formula I and at least one compound represented by formula II with at least one organic acid or an anhydride thereof in an amount that at least a portion of the nitrogens in said compounds can be acylated, whereby compounds represented by formulas V and VI are obtained:  
       
         
           
           
               
               
           
         
       
       wherein R 3  and R 4  can be independent of one another and represent C 3  to C 30  straight or branched alkyl, alkenyl or aryl groups or a heteroatom derivative thereof; R 3  and R 4  can be independent of one another and are selected from the group consisting of H, —OH, —OR, —COOH, —SH, —SR, straight chain, beta branched alkyl, alkenyl radicals and hydrocarbyl groups in oligomeric or polymeric form that are derived from propylene, isobutylene and higher olefins having terminal, internal and vinylidene double bonds, wherein R is an organic group having up to 30 carbon atom, and n is a value from 0 to 5.  
     
     
         34 . A method for providing improved durability of friction characteristics in a lubricated power transmitting apparatus comprising: 
 1) adding a fluid to an power transmitting apparatus, said fluid comprising (a) a base oil, and (b) a friction modifier comprising (i) a reaction product of an aliphatic carboxylic acid and a polyamine, said reaction product obtained under conditions sufficient to produce a mixture of 1,2-disubstituted imidazolines, said mixture containing one or more compounds represented by formula I and/or II, (ii) a reaction product obtained by (a) reacting an aliphatic carboxylic acid and a polyamine, said reaction product obtained under conditions sufficient to produce a mixture of 1,2-disubstituted imidazolines, said mixture containing one or more compounds represented by formula I and/or II, and then (b) treating under conditions to provide at least one or more compounds represented by formula III, IV, V and/or VI; or (iii) a mixture containing at least one compound represented by formula I or II and at least one compound from among the compounds represented by formula III, IV, V or VI:                          wherein R 1  and R 2  are independent of one another and are represent C 3  to C 30  straight or branched alkyl, alkenyl or aryl or heteroatom derivatives thereof; R 3  and R 4  are independent of one another and are selected from the group consisting of H, —OH, —OR, —COOH, —SH, —SR, straight chain, beta branched alkyl, alkenyl radicals and hydrocarbyl groups in oligomeric or polymeric form that are derived from propylene, isobutylene and higher olefins having terminal, internal and vinylidene double bonds, R represents an organic group having up to 30 carbon atoms, and n is a value from 0 to 5; and    2) operating the fluid in the power transmitting apparatus, wherein the duration of stability against oxidation of said fluid as a power transmission fluid is improved relative to the performance of a transmission without said fluid.    
     
     
         35 . The method of  claim 34 , wherein the base oil has a kinematic viscosity of from about 2 centistokes to about 10 centistokes at 100° C.  
     
     
         36 . The method of  claim 34 , wherein the fluid further comprises an ashless dispersant.  
     
     
         37 . The method according to  claim 34  or  36 , wherein said fluid further comprises at least one member selected from the group consisting of an antioxidant, an antifoam agent, an antiwear agent, an antirust additive, a detergent, a viscosity index improver, a copper corrosion inhibitor, a seal swell agent, a metal deactivator, and a friction modifier other than one represented by formulas I to VI.  
     
     
         38 . The method of  claim 34 , wherein the power transmitting apparatus comprises a transmission.  
     
     
         39 . The method of  claim 34 , wherein the power transmitting apparatus comprises an industrial gear or an automotive gear.  
     
     
         40 . An additive composition comprising: 
 (1) (i) a reaction product of an aliphatic carboxylic acid and a polyamine obtained under conditions sufficient to produce a mixture containing one or more compounds represented by formula I and/or II; (ii) a reaction product obtained by (a) reacting an aliphatic carboxylic acid and a polyamine under conditions sufficient to produce a mixture of 1,2-disubstituted imidazolines containing one or more compounds represented by formulas I and/or II, and then (b) treating under conditions to produce a further mixture containing one or more compounds represented by formula III, IV, V and/or VI; or (iii) a mixture containing at least one compound represented by formula I and/or II and at least one compound from among the compounds represented by formulas III to VI, wherein said formulas are:                          wherein R 1  and R 2  are independent of one another and represent C 3  to C 30  straight or branched alkyl, alkenyl or aryl or heteroatom derivatives thereof; R 3  and R 4  are independent of one another and are selected from the group consisting of H, —OH, —OR, —COOH, —SH, —SR, straight chain, beta branched alkyl, alkenyl radicals and hydrocarbyl groups in oligomeric or polymeric form that are derived from propylene, isobutylene and higher olefins having terminal, internal and vinylidene double bonds, R represents an organic group having up to 30 carbon atoms and n is a value from 0 to 5.    
     
     
         41 . A method for improving the handling characteristics of a power transmission fluid comprising adding thereto an additive according to  claim 40 .  
     
     
         42 . A fluid composition, comprising: 
 (1) a major amount of a base oil, and    (2) a minor amount of an additive comprising: 
 (i) a mixture containing one or more compounds represented by formula I and/or II; or  
 (ii) a mixture containing at least one compound represented by formula I and/or II and at least one compound from among the compounds represented by formulas III to VI, wherein said formulas are:  
                     
 wherein R 1  and R 2  are independent of one another and represent C 3  to C 30  straight or branched alkyl, alkenyl or aryl or heteroatom derivatives thereof, such as an alkyl having heteroatoms, as one example; R 3  and R 4  are independent of one another and are selected from the group consisting of H, —OH, —OR, —COOH, —SH, —SR, straight chain, branched alkyl, alkenyl radicals and hydrocarbyl groups in oligomeric or polymeric form that are derived from propylene, isobutylene and higher olefins having terminal, internal and vinylidene double bonds, R represents an alkyl or alkenyl group having up to 30 carbon atoms in linear, branched or cyclic form and n is a value from 0 to 5.  
   
     
     
         43 . An additive composition comprising 
 (1) a mixture containing one or more compounds represented by formula I and/or II; or    (2) a mixture containing at least one compound represented by formula I and/or II and at least one compound from among the compounds represented by formulas III to VI, wherein said formulas are:                          wherein R 1  and R 2  are independent of one another and represent C 3  to C 30  straight or branched alkyl, alkenyl or aryl or heteroatom derivatives thereof; R 3  and R 4  are independent of one another and are selected from the group consisting of H, —OH, —OR, —COOH, —SH, —SR, straight chain, beta branched alkyl, alkenyl radicals and hydrocarbyl groups in oligomeric or polymeric form that are derived from propylene, isobutylene and higher olefins having terminal, internal and vinylidene double bonds, R represents an organic group having up to 30 carbon atoms and n is a value from 0 to 5.    
     
     
         44 . A material resulting from the combination of an aliphatic carboxylic acid and a polyamine.  
     
     
         45 . The material of  claim 44 , wherein the material resulting from the combination comprises a 1,2-disubstituted imidazoline.  
     
     
         46 . The material of  claim 44 , wherein the molar ratio of the carboxylic acid to the polyamine is between about 1.0 to about 2.0.  
     
     
         47 . The material of  claim 44 , wherein the molar ratio of the carboxylic acid to the polyamine is between about 1.2 to about 1.6.  
     
     
         48 . The material of  claim 44 , wherein the carboxylic acid comprises one or more of a lauric, myristic, palmitic, stearic, isostearic, dodecenoic, hexadecenoic, oleic, iso-oleic, linoleic, arachidic fatty acid, or combinations thereof.  
     
     
         49 . The material of  claim 44 , wherein the carboxylic acid comprises one or more of 4-dodecylbenzoic acid, 2-hexadecylnicotinic acid, and 4-polyisobutyl acid  
     
     
         50 . The material of  claim 44 , wherein the polyamine comprises a polyethylene amine containing an internal repeating unit of —(CH 2  CH 2 NH) x —, wherein x is an integer from about 1 to about 10.  
     
     
         51 . The material of  claim 44 , wherein the polyamine comprises one or more of a diethylene triamine, a triethylene tetramine, and a tetraethylene pentamine.