Soot Dispersants and Lubricating Oil Compositions Containing Same

Abstract

Linked aromatic compounds found to act as potent soot dispersants in lubricating oil compositions; lubricating oil compositions containing such soot dispersants and precursor compounds from which the soot dispersants are derived.

1 . Compounds of the formula: 
       
         
           
           
               
               
           
         
         wherein: 
         each Ar independently represents an aromatic moiety having 0 to 3 substituents selected from the group consisting of alkyl, alkoxy, alkoxyalkyl, aryloxy, aryloxyalkyl, hydroxy, hydroxyalkyl, halo and combinations thereof; 
         each L is independently a linking moiety comprising a carbon-carbon single bond or a linking group; 
         each Y is —OR″ wherein each R″ is independently selected from C 1  to C 100  alkyl and aryl; 
         each a is independently 0 to 3, with the proviso that at least one Ar moiety bears at least one group Y; and 
         m is 1 to 100. 
       
     
     
         2 . Compounds of  claim 1 , wherein m is 2 to 100. 
     
     
         3 . Compounds of the formula: 
       
         
           
           
               
               
           
         
         wherein: 
         each Ar independently represents an aromatic moiety having 0 to 3 substituents selected from the group consisting of alkyl, alkoxy, alkoxyalkyl, aryloxy, aryloxyalkyl, hydroxy, hydroxyalkyl, halo and combinations thereof; 
         each L is independently a linking moiety comprising a carbon-carbon single bond or a linking group; 
         from about 2% to about 98% of the Y units are each independently —OR″; and from about 98% to about 2% of the Y units are one or more moiety of the formula H(O(CR 2 ) n ) y X—, wherein X is selected from the group consisting of (CR′ 2 ) z , O and S; R and R′ are each independently selected from H, C 1  to C 6  alkyl and aryl; R″ is selected from C 1  to C 100  alkyl and aryl; z is 1 to 10; n is 0 to 10 when X is (CR′ 2 ) z , and 2 to 10 when X is O or S; and y is 1 to 30; 
         each a is independently 0 to 3, with the proviso that at least one Ar moiety bears at least one group Y; and 
         m is 1 to 100. 
       
     
     
         4 . Compounds of  claim 3 , wherein m is 2 to 100. 
     
     
         5 . Compounds of  claim 3 , wherein from about 2% to about 98% of Y units are H(O(CR 2 ) 2 ) y O—, wherein y is 1 to 6, and from about 98% to 2% of Y units are —OR″. 
     
     
         6 . Compounds of  claim 5 , wherein Ar is naphthalene; from about 40% to about 90% of Y units are HOCH 2 CH 2 O—, and from about 90% to 10% of Y units are —OCH 3 ; and L is CH 2 . 
     
     
         7 . Compounds of  claim 6 , wherein from about 65 mol. % to about 75 mol. % of Y units are HOCH 2 CH 2 O—, and from about 35 mol. % to about 25 mol. % of Y units are —OCH 3 . 
     
     
         8 . Compounds of  claim 7  derived from about 65 mol. % to about 75 mol. % of 2-(2-naphthoxy)-ethanol and from about 35 mol. % to about 25 mol. ° A) of 2-methoxy naphthalene, wherein m is 1 to about 25. 
     
     
         9 . A process for forming compounds, or mixtures of compounds, of  claim 8  comprising reaction of naphthyloxyethanol and 2-methoxylnaphthalene with formaldehyde in the presence of an acid. 
     
     
         10 . The process of  claim 9 , wherein naphthoxyethanol is the product of a process comprising reaction of a hydroxyl-naphthylene compound with ethylene carbonate in the presence of a base catalyst. 
     
     
         11 . The process of  claim 10 , wherein remaining base is neutralized with an excess of acid prior to introduction of said formaldehyde. 
     
     
         12 . The process of  claim 11 , wherein said acid is selected from oil soluble sulfonic acid and solid acid catalyst. 
     
     
         13 . A reaction product of one or more compounds as claimed in  claim 1 , and an acylating agent. 
     
     
         14 . The reaction product of  claim 13 , wherein said acylating agent is at least one selected from polyalkyl succinic acylating agent and polyalkenyl succinic acylating agent derived from polyalkene having  M n of from about 100 to about 5000. 
     
     
         15 . The reaction product of  claim 13 , wherein said acylating agent is hydrocarbyl isocyanate. 
     
     
         16 . A reaction product of one or more compounds as claimed in  claim 2 , and an acylating agent. 
     
     
         17 . The reaction product of  claim 16 , wherein said acylating agent is at least one selected from polyalkyl succinic acylating agent and polyalkenyl succinic acylating agent derived from polyalkene having  M n of from about 100 to about 5000. 
     
     
         18 . The reaction product of  claim 16 , wherein said acylating agent is hydrocarbyl isocyanate. 
     
     
         19 . The reaction product of a mixture of methylene-bridged naphthoxyethanol and 2-methoxy naphthalene compounds, and an acylating agent selected from polyalkyl succinic acylating agent and polyalkenyl succinic acylating agent. 
     
     
         20 . A process for forming the product of  claim 19 , wherein said mixture of methylene-bridged naphthoxyethanol and 2-methoxy naphthalene compounds, and acylating agent are reacted in the presence of an acid catalyst. 
     
     
         21 . The process of  claim 20 , wherein said methylene-bridged naphthoxyethanol and 2-methoxy naphthalene compounds are the products of a process comprising (i) reacting hydroxyl-naphthalene compound and ethylene carbonate in the presence of a base catalyst to form naphthyloxyethanol; (ii) neutralizing said base with an excess of acid to provide an intermediate; and (iii) reacting said intermediate with 2-methoxy naphthalene and formaldehyde in the presence of residual acid. 
     
     
         22 . The process of  claim 21 , wherein said acid is selected from oil soluble liquid acid catalyst and solid acid catalyst. 
     
     
         23 . The process of  claim 22 , wherein said acylating agent is polybutenyl succininc acylating agent derived from polybutene having  M n of from about 300 to about 5000. 
     
     
         24 . The process of  claim 23 , wherein a ratio of total moles of succinic acylating moieties to total moles of naphthyl moieties of said naphthyloxyethanol and said 2-methoxy naphthalene is from about 1.10 to about 0.5.