Methods and compositions for inhibiting polymerization of ethylenically unsaturated hydrocarbons

Abstract

Methods and compositions for inhibiting the polymerization of ethylenically unsaturated hydrocarbons are disclosed. Combinations of aminophenol compound and either of phenylenediamine or hydroxylamine compounds are effective at inhibiting this polymerization under both processing and storage conditions.

Having thus described the invention, what I claim is:  
     
         1 . A method for inhibiting the polymerization of ethylenically unsaturated hydrocarbons comprising adding to said hydrocarbons an effective inhibiting amount of a composition comprising an aminophenol compound and at least one of a phenylenediamine compound and a hydroxylamine compound.  
     
     
         2 . The method as claimed in    claim 1    wherein said aminophenol compound is selected from the group consisting of para-aminophenol, meta-aminophenol and ortho-aminophenol.  
     
     
         3 . The method as claimed in    claim 1    wherein said phenylenediamine compound has the formula:  
                 
 
       wherein R 1 , R 2 , R 3  and R 4  are the same or different and are hydrogen, alkyl, aryl, alkaryl, and aralkyl having about 1 to about 20 carbon atoms.  
     
     
         4 . The method as claimed in    claim 1    wherein said hydroxylamine compound has the formula:  
                 
 
       wherein R 5  and R 6  are the same or different and are hydrogen, alkyl, aryl, alkaryl, aralkyl or hydroxyalkyl groups and have about three to about twenty carbon atoms.  
     
     
         5 . The method as claimed in    claim 2    wherein said aminophenol compound is ortho-aminophenol.  
     
     
         6 . The method as claimed in    claim 3    wherein said phenylenediamine compound is selected from the group consisting of N,N′-bis-di-sec-butyl-p-phenylenediamine and N-phenyl-N′-(1,4-dimethylpentyl)-p-phenylenediamine.  
     
     
         7 . The method as claimed in    claim 4    wherein said hydroxylamine compound is selected from the group consisting of N,N′-diethylhydroxylamine and bis-N,N′-(hydroxypropyl-hydroxylamine).  
     
     
         8 . The method as claimed in    claim 1    wherein said ethylenically unsaturated hydrocarbons are undergoing processing.  
     
     
         9 . The method as claimed in    claim 1    wherein said ethylenically unsaturated hydrocarbons are in storage conditions.  
     
     
         10 . The method as claimed in    claim 1    wherein said processing conditions are at temperatures of about 95° to about 125° C.  
     
     
         11 . The method as claimed in    claim 1    wherein said ethylenically unsaturated hydrocarbons are selected from the group consisting of olefins and diolefins.  
     
     
         12 . The method as claimed in    claim 11    wherein said olefins and said diolefins contain about 2 to about 20 carbons.  
     
     
         13 . The method as claimed in    claim 1    wherein said composition is added to said hydrocarbon in an amount ranging from about 1 to about 10,000 parts per million parts of said hydrocarbon.  
     
     
         14 . A composition comprising an aminophenol compound and at least one of a phenylenediamine compound and a hydroxylamine compound.  
     
     
         15 . The composition as claimed in    claim 14    wherein said aminophenol compound is selected from the group consisting of para-aminophenol, meta-aminophenol and ortho-aminophenol.  
     
     
         16 . The composition as claimed in    claim 14    wherein said phenylenediamine compound has the formula:  
                 
 
       wherein R 1 , R 2 , R 3  and R 4  are the same or different and are hydrogen, alkyl, aryl, alkaryl, and aralkyl having about 1 to about 20 carbon atoms.  
     
     
         17 . The composition as claimed in    claim 14    wherein said hydroxylamine compound has the formula:  
                 
 
       wherein R 5  and R 6  are the same or different and are hydrogen, alkyl aryl, alkaryl, aralkyl or hydroxyalkyl groups and have about three to about twenty carbon atoms.  
     
     
         18 . The composition as claimed in    claim 15    wherein said aminophenol compound is ortho-aminophenol.  
     
     
         19 . The composition as claimed in    claim 16    wherein said phenylenediamine compound is selected from the group consisting of N,N′-bis-di-sec-butyl-p-phenylenediamine and N-phenyl-N′-(1,4-dimethylpentyl)-p-phenylenediamine.  
     
     
         20 . The composition as claimed in    claim 17    wherein said hydroxylamine compound is selected from the group consisting of N,N′-diethylhydroxylamine and bis-N,N′-(hydroxypropyl-hydroxylamine).  
     
     
         21 . The composition as claimed in    claim 14    further comprising either a phenylenediamine compound and a hydroxylamine compound.  
     
     
         22 . The composition as claimed in    claim 14    further comprising an ethylenically unsaturated hydrocarbon.  
     
     
         23 . The composition as claimed in    claim 14    wherein the weight ratio of aminophenol compound to either of said phenylenediamine compound and hydroxylamine compound ranges from about 1:9 to about 9:1.