Low-odor dimethicone copolyol sulfosuccinate surfactant compositions

Abstract

Dimethicone copolyol sulfosuccinate surfactant compounds having low-odor characteristics are disclosed. The low-odor dimethicone copolyol sulfosuccinate is substantially free from propionaldehyde and acid-releasable precursors of propionaldehyde, thereby substantially eliminating the cosmetically undesirable odor characteristic of conventional dimethicone copolyol sulfosuccinate surfactants. The low-odor dimethicone copolyol sulfosuccinates are suitable for use as surfactants in household or personal care products and applications.

1 . A low-odor composition suitable for use in cosmetic and personal care applications comprising a compound having a dimethicone copolyol portion and a sulfosuccinate portion, the compound having the formula:  
       
         
           
           
               
               
           
         
       
       wherein the composition is substantially free of propionaldehyde and acid-releasable precursors of propionaldehyde; R is a polymer of ethylene oxide, a polymer of propylene oxide, a polymer of butylene oxide, a polymer of tetrahydrofuran, a polymer of glycerol, or a copolymer of two or more monomers selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, and glycerol; M+ is an alkali metal cation or ammonium group; x has a value in the range of 0 to about 100 and y has a value in the range of 1 to about 100.  
     
     
         2 . The composition of  claim 1  wherein R is selected from the group consisting of: 
         —(C 2 H 4 O) S —C 2 H 4 —; —(C 3 H 6 O) t —C 3 H 6 —; and —(C 2 H 4 O) v —(C 3 H 6 O) w —Y—; 
       wherein s and t each independently have a value in the range of 2 to about 30; v and w each independently have a value in the range of 1 to about 30; and Y is C 2 H 4  or C 3 H 6 .  
     
     
         3 . The composition of  claim 1  wherein the dimethicone copolyol portion has a calculated HLB value in the range of about 10 to about 17.  
     
     
         4 . The composition of  claim 1  wherein the compound has an equivalent weight in the range of about 400 to about 3000 grams per equivalent.  
     
     
         5 . A low-odor composition suitable for use in cosmetic and personal care applications comprising a compound having a dimethicone copolyol portion and a sulfosuccinate portion, the compound having the formula:  
       
         
           
           
               
               
           
         
         wherein the composition is substantially free of propionaldehyde and acid-releasable precursors of propionaldehyde; R is a polymer of ethylene oxide, a polymer of propylene oxide, a polymer of butylene oxide, a polymer of tetrahydrofuran, a polymer of glycerol, or a copolymer of two or more monomers selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, and glycerol; M′(+2) is an alkaline earth metal cation; x has a value in the range of 0 to about 100 and y has a value in the range of 1 to about 100.  
       
     
     
         6 . The composition of  claim 5  wherein R is selected from the group consisting of: 
         —(C 2 H 4 O) S —C 2 H 4 —; —(C 3 H 6 O) t —C 3 H 6 —; and —(C 2 H 4 O) V —(C 3 H 6 O) w —Y—; 
       wherein s and t each independently have a value in the range of 2 to about 30; v and w each independently have a value in the range of 1 to about 30; and Y is C 2 H 4  or C 3 H 6 .  
     
     
         7 . The composition of  claim 5  wherein the dimethicone copolyol portion has a calculated HLB value in the range of about 10 to about 17.  
     
     
         8 . The composition of  claim 5  wherein the compound has an equivalent weight in the range of about 400 to about 3000 grams per equivalent.  
     
     
         9 . A low-odor composition suitable for use in cosmetic and personal care applications comprising a compound having a dimethicone copolyol portion and a sulfosuccinate portion, the compound having the formula:  
       
         
           
           
               
               
           
         
       
       wherein the composition is substantially free of propionaldehyde and acid-releasable precursors of propionaldehyde; X+ is an ammonium group derived from an amino alcohol, an amine ethoxylate or an amine propoxylate; R is a polymer of ethylene oxide, a polymer of propylene oxide, a polymer of butylene oxide, a polymer of tetrahydrofuran, a polymer of glycerol, or a copolymer of two or more monomers selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, and glycerol; M+ is an alkali metal cation or ammonium group; x has a value in the range of 0 to about 100 and y has a value in the range of 1 to about 100.  
     
     
         10 . The composition of  claim 9  wherein the ammonium group, X+, is derived from at least one amine selected from the group consisting of monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine and diglycolamine.  
     
     
         11 . The composition of  claim 9  wherein R is selected from the group consisting of: 
         —(C 2 H 4 O) S —C 2 H 4 —; —(C 3 H 6 O) t —C 3 H 6 —; and —(C 2 H 4 O) V —(C 3 H 6 O) W —Y—; 
       wherein s and t each independently have a value in the range of 2 to about 30; v and w each independently have a value in the range of 1 to about 30; and Y is C 2 H 4  or C 3 H 6 .  
     
     
         12 . The composition of  claim 9  wherein the dimethicone copolyol portion has a calculated HLB value in the range of about 10 to about 17.  
     
     
         13 . The composition of  claim 9  wherein the compound has an equivalent weight in the range of about 400 to about 3000 grams per equivalent.  
     
     
         14 . A low-odor composition suitable for use in cosmetic and personal care applications comprising a compound having a dimethicone copolyol portion and a sulfosuccinate portion, the compound having the formula:  
       
         
           
           
               
               
           
         
         wherein the composition is substantially free of propionaldehyde and acid-releasable precursors of propionaldehyde; X+ is an ammonium group derived from an amino alcohol, an amine ethoxylate or an amine propoxylate; R is a polymer of ethylene oxide, a polymer of propylene oxide, a polymer of butylene oxide, a polymer of tetrahydrofuran, a polymer of glycerol, or a copolymer of two or more monomers selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, and glycerol; x has a value in the range of 0 to about 100 and y has a value in the range of 1 to about 100.  
       
     
     
         15 . The composition of  claim 14  wherein the ammonium group, X+, is derived from at least one amine selected from the group consisting of monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine and diglycolamine.  
     
     
         16 . The composition of  claim 14  wherein R is selected from the group consisting of: 
         —(C 2 H 4 O) S —C 2 H 4 —; —(C 3 H 6 O) t —C 3 H 6 —; and —(C 2 H 4 O) v —(C 3 H 6 O) w —Y—; 
       wherein s and t each independently have a value in the range of 2 to about 30; v and w each independently have a value in the range of 1 to about 30; and Y is C 2 H 4  or C 3 H 6 .  
     
     
         17 . The composition of  claim 14  wherein the dimethicone copolyol portion has a calculated HLB value in the range of about 10 to about 17.  
     
     
         18 . The composition of  claim 14  wherein the compound has an equivalent weight in the range of about 400 to about 3000 grams per equivalent.  
     
     
         19 . A method of producing a relatively low-odor dimethicone copolyol sulfosuccinate that is substantially free from propionaldehyde and acid-releasable precursors of propionaldehyde, the method comprising the steps of: 
 reacting a dimethicone copolyol with maleic anhydride to form a maleic monoester, the dimethicone copolyol being substantially free of propionaldehyde and acid-releasable precursors of propionaldehyde; and    sulfonating the maleic monoester with a compound selected from the group consisting of an alkali metal sulfite, an alkaline earth sulfite, ammonium sulfite, an amino sulfite, and a combination of any of the foregoing with an amino alcohol.    
     
     
         20 . The method of  claim 15  wherein the dimethicone copolyol has an equivalent weight in the range of about 350 to about 1100 grams per equivalent.  
     
     
         21 . The method of  claim 15  wherein the dimethicone copolyol has a calculated HLB value in the range of about 10 to about 17.  
     
     
         22 . A household or personal care product comprising at least one low-odor composition of  claim 1  and a physiologically tolerable vehicle.  
     
     
         23 . A household or personal care product comprising at least one low-odor composition of  claim 5  and a physiologically tolerable vehicle.  
     
     
         24 . A household or personal care product comprising at least one low-odor composition of  claim 9  and a physiologically tolerable vehicle.  
     
     
         25 . A household or personal care product comprising at least one low-odor composition of  claim 14  and a physiologically tolerable vehicle.