Emulsifiers, especially based on polyisobutylenamines

Abstract

Compounds, in particular those based on polyisobutyleneamines, are suitable as emulsifiers for water-in-oil emulsions and are used in particular as additives for fuels and lubricants. The novel compounds are those of the formula I where R 1 is unsubstituted or C 1 -C 12 -alkyl-substituted C 1 -C 8 -alkylene or C 2 -C 8 -alkenylene, R 2 is linear or branched C 8 -C 350 -alkyl or C 8 -C 350 -alkenyl, R 3 and R 4 , independently of one another, are each H, methyl or ethyl and together have not more than 2 carbon atoms, R 5 is H, M + , SO 3 H, SO 3 − M + , OPO 3 H, OPO 3 − M + or C(O)R 7 , M + is NH 4 + , an alkali metal ion or 0.5 alkaline earth metal ion, R 7 is a linear C 2 - to C 10 -hydrocarbon radical substituted by at least one hydrophilic group and y and z, independently of one another, are each an integer from 0 to 50, and R 5 is H if y is 0, and R 6 is H if z is 0.

We claim:  
     
         1 . A compound of the formula I  
       
         
           
           
               
               
           
         
       
       where R 1  is unsubstituted or C 1 -C 12 -alkyl-substituted C 1 -C 8 -alkylene or C 2 -C 8 -alkenylene, preferably unsubstituted C 2 -C 4 -alkylene, 
 R 2  is linear or branched C 8 -C 350 -alkyl or C 8 -C 3-50 -alkenyl, preferably C 22 -C 350 -polyisobutenyl, R 3  and R 4 , independently of one another, are each H, methyl or ethyl and together have not more than 2 carbon atoms,  
 R 5  and R 6 , independently of one another, are each H, M + , SO 3 H, SO 3   − M + , OPO 3 H, OPO 3   − M +  or C(O)R 7 ,  
 M +  is NH 4   + , an alkali metal ion or 0.5 alkaline earth metal ion,  
 R 7  is a linear C 2 -C 10 -hydrocarbon radical substituted by at least one hydrophilic group and  
 y and z, independently of one another, are each an integer from 0 to 50,  
 and R 5  is H if y is 0, and R 6  is H if z is 0.  
 
     
     
         2 . A compound as claimed in  claim 1 , wherein R 2  is a polyisobutenyl having a number average molar mass of from 300 to 5000, preferably from 500 to 2300, particularly preferably from 500 to 1000.  
     
     
         3 . A compound as claimed in  claim 1  or  claim 2 , where R 5  and R 6  are each C(O)R 7 , wherein R 7  corresponds to the formula VI  
       
         
           
           
               
               
           
         
       
       where n is an integer from 1 to 4.  
     
     
         4 . A process for the preparation of a compound (I) as claimed in any of  claims 1  to  3  by reacting dicarboxylic acids HO 2 C—R 1 —O 2 H with amines R 2 —NH 2  and alkylene oxides of the formula III in a suitable sequence,  
       
         
           
           
               
               
           
         
       
       and, if required, by reacting the compound obtained in this manner with SO 3 , P 4 O 10  or compounds R 7 C(O)OH  
       and, if required, then with NH 3  or alkali metal (alkaline earth metal) salts.  
     
     
         5 . A compound of the formula II  
       
         
           
           
               
               
           
         
       
       where R 1  is unsubstituted or C 1 -C 12 -alkyl-substituted C 1 -C 8 -alkylene or C 2 - to C 8 alkenylene, and 
 R 2  is linear or branched C 8 -C 350 -alkyl or C 8 -C 350 -alkenyl.  
 
     
     
         6 . A compound of the formula IV  
       
         
           
           
               
               
           
         
       
       where R 2  is linear or branched C 8 -C 350 -alkyl or C 8 -C 350 -alkenyl, 
 R 3  and R 4 , independently of one another, are each H, methyl or ethyl and together contain not more than 2 carbon atoms, and  
 R 5  is H, M+, SO 3 H, SO 3   − M + , OPO 3 H, OPO 3   − M +  or C(O)R 7 ,  
 M +  is NH 4   + , an alkali metal ion or 0.5 alkaline earth metal ion and  
 R 7  is a linear C 2 -C 10 -hydrocarbon radical substituted by at least one hydrophilic group.  
 
     
     
         7 . A compound of the formula V  
       
         
           
           
               
               
           
         
       
       where R 1  is unsubstituted C 1 -C 12 -alkyl-substituted C 1 -C 8 -alkylene or C 2 -C 8 alkenylene, 
 R 2  is linear or branched C 8 -C 350 -alkyl or C 8 -C 350 -alkenyl,  
 R 3  and R 4 , independently of one another, are each H, methyl or ethyl and together contain not more than 2 carbon atoms,  
 R 5  and R 6 , independently of one another, are each H, M + , SO 3 H, SO 3   − M + , OPO 3 H, OPO 3   − M +  or C(O)R 7 ,  
 M +  is NH 4   + , an alkali metal ion or 0.5 alkaline earth metal ion, and  
 R 7  is a linear C 2 -C 10 -hydrocarbon radical substituted by at least one hydrophilic group.  
 
     
     
         8 . The use of a compound as claimed in any of  claims 1  to  3 , preferably of a compound in which R 5  and R 6  are each H, as an emulsifier in the preparation of water-in-oil emulsions, the oil being a vegetable, animal or synthetic oil or fat.  
     
     
         9 . The use of a compound as claimed in any of  claims 1  to  3 , preferably of a compound in which R 5  and R 6  are not H, as an emulsifier of a fuel in the preparation of water-in-fuel emulsions.  
     
     
         10 . A water-in-fuel emulsion resulting from the use as claimed in  claim 9  and containing from 60 to 95% by weight of fuel, preferably diesel fuel, from 3 to 35% by weight of water and from 0.2 to 10, preferably from 0.5 to 5, % by weight of a novel compound as claimed in any of  claims 1  to  3 , preferably of a compound in which R 5  and R 6  are not H, as an emulsifier.  
     
     
         11 . An emulsion as claimed in  claim 10 , wherein, in addition to the novel compound, one or more further emulsifiers, preferably sorbitan monooleate, C 13 -oxo alcohol ethoxylates or alkylphenol ethoxylates, are present.  
     
     
         12 . A process for the preparation of an emulsion as claimed in  claim 10  or  11 , wherein the respective components are mixed with one another and are emulsified in a manner known per se, preferably in a mixing nozzle.  
     
     
         13 . The use of a compound as claimed in any of  claims 1  to  3  as a surfactant, antiwear additive or lubricity-improving or corrosion-inhibiting additive in fuels, lubricants, fuel additive concentrates and lubricant additive concentrates or as a corrosion-inhibiting additive in aqueous liquids.  
     
     
         14 . A fuel, lubricant, fuel additive concentrate, lubricant additive concentrate or aqueous liquid resulting from the use as claimed in  claim 13  and containing at least one compound as claimed in any of  claims 1  to  3 .