Purified polyoxypropylene fatty acid isopropanolamide surfactants, production thereof and detergent compositions containing the surfactants

Abstract

A refined product of a polyoxypropylene fatty acid isopropanolamide surfactant, having a high stability in storage and a very small change in smell thereof, is obtained by heat-treating an addition-reaction mixture prepared from a compound of the formula (III) and propylene oxide in a molar amount of 0.5 to 10 times that of the compound of the formula (III), and containing the target compound of the formula (I) and an oxazoline compound of the formula (II) produced as a by-product with water or an alkaline aqueous solution at 50 to 100° C., to hydrolyze the oxyazoline compound and to control the content of the oxyazoline compound to 0.1% by mass or less; and a detergent composition containing the refined product in a content of 1 to 50% by mass, exhibits enhanced thickening, foaming, emulsifying, dispersing and dissolving properties. R 1 —CONH—CH 2 CH(CH 3 ) (X) n OH  (I)  R 1 —CONH—CH 2 CH(CH 3 )—OH  (III) [R 1 =C 1 -C 19 alkyl or alkenyl group, X=oxypropylene group, n=average number of addition-reacted X groups of 0.5 to 10]

1 . A refined product of a polyoxypropylene fatty acid isopropanolamide surfactant comprising, as a principal component, a surface active polyoxypropylene fatty acid isopropanolamide compound represented by the general formula (I):  
       
         
           
           
               
               
           
         
       
       in which formula (I), R 1  represents an alkyl or alkenyl group having 5 to 19 carbon atoms, X represents an oxypropylene group, and n represents an average number of the addition-reacted X groups of 0.5 to 10.0 per molecule of the compound, 
 characterized in that the refined product contains, as an impurity, an oxazoline compound of the general formula (II):  
                     
 in which formula (II), R 1  is as defined above, in a controlled content of 0.1% by mass or less based on the mass of the compound of the formula (I).  
 
     
     
         2 . The refined product of the polyoxypropylene fatty acid isopropanolamide surfactant as claimed in  claim 1 , wherein the surface active polyoxypropylene fatty acid isopropanolamide compound of the general formula (I) and the oxazoline compound of the general formula (II) are ones produced by an addition reaction of a fatty acid monoisopropanolamide represented by the general formula (III):  
       
         
           
           
               
               
           
         
       
       in which formula (III), R 1  is as defined above, with propylene oxide in an average amount of 0.5 to 10 moles per mole of the compound of the formula (III).  
     
     
         3 . A process for producing a refined product of a polyoxypropylene fatty acid isopropanolamide surfactant comprising addition reacting a fatty acid monoisopropanolamide represented by the general formula (III):  
       
         
           
           
               
               
           
         
       
       in which formula (III), R 1  represents an alkyl or alkenyl group having 5 to 19 carbon atoms, with propylene oxide in a molar amount of 0.5 to 10 times that of the compound of the formula (III), to produce a reaction mixture of a surface active polyoxypropylene fatty acid isopropanolamide compound of the general formula (I) with, as a side reaction product, an oxazoline compound of the formula (II):  
       
         
           
           
               
               
           
         
       
       in which formulae (I) and (II), R 1  is as defined above, X represents an oxypropylene group and n represents an average number of moles of the addition-reacted X group of 0.5 to 10; 
 mixing water or an aqueous alkaline solution into the reaction mixture, to prepare a refining reaction system;  
 heating the refining reaction system to a temperature of 50 to 100° C. to hydrolyze the oxazoline compound of the general formula (II) and to thereby reduce the content of the oxazoline compound of the general formula (II) in the reaction mixture to 0.1% by mass or less based on the mass of the compound of the formula (I); and  
 collecting the refined product of polyoxypropylene fatty acid isopropanolamide surfactant comprising the compound of the formula (I) from the reaction system.  
 
     
     
         4 . The process for producing a refined product of a polyoxypropylene fatty acid isopropanolamide surfactant as claimed in  claim 3 , wherein the pH value of the refining reaction system is adjusted to 7.5 to 12.0.  
     
     
         5 . The process for producing a refined product of a polyoxypropylene fatty acid isopropanolamide surfactant as claimed in  claim 3  or  4 , wherein the aqueous alkaline solution to be contained in the refining reaction system is selected from aqueous solutions of at least one member selected from sodium hydroxide, potassium hydroxide and lithium hydroxide.  
     
     
         6 . A detergent composition comprising the refined product of the polyoxypropylene fatty acid isopropanolamide surfactant as claimed in  claim 1  or  2 , in a content of 0.1 to 50% by mass.