Mixtures of sulfuric esters

Abstract

The invention relates to novel mixtures of sulfuric esters and specific sulfuric esters that are useful as leveling agents for the dyeing of nitrogenous fiber materials and to a process for their preparation by reacting sulfuryl chloride with specific alcohols.

1 . A mixture of sulfuric esters of formula (1)  
       
         
           
           
               
               
           
         
         wherein  
         R 1  is an aliphatic radical having 1 to 30 carbon atoms,  
         R 2  is a radical of formula (2)  
         
           
             
             
                 
                 
             
           
           wherein  
           n is an integer from 0 to 30,  
           m is an integer from 1 to 29,  
           X is an aliphatic radical having 4 to 24 carbon atoms, and  
           Y is H or SO 2 (OM), where M represents hydrogen, alkali metal, ammonium, mono-, di-, tri-, or tetra(C 1 -C 6 -alkyl)ammonium, or mono-, di-, tri-, or tetra(C 2 -C 6 -alkanol)ammonium ions,  
         
         R 3  is a radical of formula (3)  
         
           
             
             
                 
                 
             
           
           wherein  
           p is an integer from 4 to 35,  
           R 4  is H, methyl, ethyl, phenyl, or mixtures of H and methyl, and  
           Z is H, methyl, ethyl, or SO 2 (OM), where M represents hydrogen, alkali metal, ammonium, mono-, di-, tri-, or tetra-(C 1 -C 6 -alkyl)ammonium, or mono-, di-, tri-, or tetra(C 2 -C 6 -alkanol)ammonium ions, and  
         
         a, b, and c are identical or different and are 0, 1, or 2, with the proviso that a+b+c is 2,  
         obtained by reacting sulfuryl chloride with a mixture of the alcohols R 1 OH, R 2 OH, and R 3 OH, wherein R 1 , R 2 , and R 3  have the same meanings as for formula (1) except that Y is exclusively hydrogen and Z is hydrogen, methyl, or ethyl.  
       
     
     
         2 . A mixture of sulfuric esters according to  claim 1  wherein 
 R 1  is an aliphatic radical having 4 to 30 carbon atoms,    R 2  is a radical of formula (2)                        wherein    n is an integer from 0 to 10,    m is an integer from 1 to 10,    X is an aliphatic radical having 12 to 24 carbon atoms, and    Y is H or SO 2 (OM), where M independently represents hydrogen, alkali metal, ammonium, mono-, di-, tri-, or tetra-(C 1 -C 6 -alkyl)ammonium, or mono-, di-, tri-, or tetra(C 2 -C 6 -alkanol)ammonium ions,      R 3  is a radical of formula (3)                        wherein    p is an integer from 3 to 35,    R 4  is H or methyl, and    Z is H, methyl, ethyl, or SO 2 (OM), where M independently represents hydrogen, alkali metal, ammonium, mono-, di-, tri-, or tetra(C 1 -C 6 -alkyl)ammonium, or mono-, di-, tri-, or tetra(C 2 -C 6 -alkanol)ammonium ions, and      a, b, and c are identical or different and are 0, 1, or 2, with the proviso that a+b+c is 2.    
     
     
         3 . A mixture of sulfuric esters according to  claim 1  wherein 
 R 1  is an aliphatic radical having 8 to 20 carbon atoms,    R 2  is a radical of formula (2)                        wherein    n is an integer from 0 to 5,    m is an integer from 1 to 5,    X is an aliphatic radical having 16 to 22 carbon atoms, and    Y is H,      R 3  is a radical of formula (3)                        wherein    p is an integer from 9 to 22,    R 1  is H, and    z is H, and      a, b, and c are identical or different and are 0, 1, or 2 with the proviso that a+b+c is 2.    
     
     
         4 . A process for preparing a mixture of sulfuric esters according to  claim 1  comprising reacting sulfuryl chloride with a mixture of the alcohols R 1 OH, R 2 OH, and R 3 OH, wherein 
 R 1  is an aliphatic radical having 1 to 30 carbon atoms,    R 2  is a radical of formula (2)                        wherein    n is an integer from 0 to 30,    m is an integer from 1 to 29,    X is an aliphatic radical having 4 to 24 carbon atoms, and    Y is H, and      R 3  is a radical of formula (3)                        wherein    p is an integer from 4 to 35,    R 4  is H, methyl, ethyl, phenyl, or mixtures of H and methyl, and    Z is H, methyl, or ethyl.      
     
     
         5 . A process according to  claim 4  wherein 3 mol of the mixture of the alcohols R 1 OH, R 2 OH, and R 3 OH are reacted with 1.5 to 2.5 mol of sulfuryl chloride.  
     
     
         6 . A process according to  claim 4  wherein the alcohols R 1 OH, R 2 OH, and R 3 OH are used in the quantity ratios 
 R 1 OH 10 to 40 mol %    R 2 OH 20 to 80 mol %, and    R 3 OH 10 to 40 mol %,    the amounts of the three alcohols totaling 100 mol %.    
     
     
         7 . A sulfuric ester of formula (1)  
       
         
           
           
               
               
           
         
         wherein  
         R 1  is an aliphatic radical having 1 to 30 carbon atoms,  
         R 2  is a radical of formula (2)  
         
           
             
             
                 
                 
             
           
           wherein  
           n is an integer from 0 to 30,  
           m is an integer from 1 to 29,  
           X is an aliphatic radical having 4 to 24 carbon atoms, and  
           Y is H or SO 2 (OM), where M represents hydrogen, alkali metal, ammonium, mono-, di-, tri-, or tetra(C 1 -C 6 -alkyl)ammonium, or mono-, di-, tri-, or tetra(C 2 -C 8 -alkanol)ammonium ions,  
         
         R 3  is a radical of formula (3)  
         
           
             
             
                 
                 
             
           
           wherein  
           p is an integer from 4 to 35,  
           R 4  is H, methyl, ethyl, phenyl, or mixtures of H and methyl, and  
           Z is H, methyl, ethyl, or SO 2 (OM), where M represents hydrogen, alkali metal, ammonium, mono-, di-, tri-, or tetra-(C 1 -C 6 -alkyl)ammonium, or mono-, di-, tri-, or tetra(C 2 -C 6 -alkanol)ammonium ions, and  
         
         a, b, and c are identical or different and are 0 or 1, with the proviso that a+b+c is 2.  
       
     
     
         8 . A sulfuric ester according to  claim 7  wherein 
 R 1  is an aliphatic radical having 4 to 30 carbon atoms,    R 2  is a radical of formula (2)                        wherein    n is an integer from 0 to 10,    m is an integer from 1 to 10,    X is an aliphatic radical having 12 to 24 carbon atoms, and    Y is H or SO 2 (OM), where M independently represents hydrogen, alkali metal, ammonium, mono-, di-, tri-, or tetra(C 1 -C 6 -alkyl)ammonium, or mono-, di-, tri-, or tetra(C 2 -C 6 -alkanol)ammonium ions,      R 3  is a radical of formula (3)                        wherein    p is an integer from 3 to 35,    R 4  is H or methyl, and    Z is H, methyl, ethyl, or SO 2 (OM), where M independently represents hydrogen, alkali metal, ammonium, mono-, di-, tri-, or tetra(C 1 -C 6 -alkyl)ammonium, or mono-, di-, tri-, or tetra(C 2 -C 6 -alkanol)ammonium ions, and    a, b, and c are identical or different and are 0 or 1, with the proviso that a+b+c is 2.      
     
     
         9 . A sulfuric ester according to  claim 7  wherein 
 R 1  is an aliphatic radical having 8 to 20 carbon atoms,    R 2  is a radical of formula (2)                        wherein    n is an integer from 0 to 5,    m is an integer from 1 to 5,    X is an aliphatic radical having 16 to 22 carbon atoms, and    Y is H,      R 3  is a radical of formula (3)                        wherein    p is an integer from 9 to 22,    R 1  is H, and    Z is H, and    a, b, and c are identical or different and are 0 or 1, with the proviso that a+b+c is 2.      
     
     
         10 . An organic or aqueous-organic formulation comprising 25 to 70% by weight of a mixture of sulfuric esters according to  claim 1 .  
     
     
         11 . An organic or aqueous-organic formulation according to  claim 10  wherein the organic component of the formulation comprises one or more organic solvents selected from the group consisting of mono-, di-, and oligoethylene glycols, oligopropylene glycols, and oligoethylene/propylene glycols, and mono- and diethers thereof.  
     
     
         12 . An organic or aqueous-organic formulation comprising 25 to 70% by weight of a mixture of sulfuric esters according to  claim 7 .  
     
     
         13 . An organic or aqueous-organic formulation according to  claim 12  wherein the organic component of the formulation comprises one or more organic solvents selected from the group consisting of mono-, di-, and oligoethylene glycols, oligopropylene glycols, and oligoethylene/propylene glycols, and mono- and diethers thereof.  
     
     
         14 . A method comprising dyeing nitrogenous fiber materials in the presence of an auxiliary wherein the auxiliary is a sulfuric ester according to  claim 1 .  
     
     
         15 . A method according to  claim 14  wherein the dyeing is carried out with an acid dye, a 1:1 metal complex dye, a 1:2 metal complex dye, a chromium dye, or mixtures thereof.  
     
     
         16 . A method comprising dyeing nitrogenous fiber materials in the presence of an auxiliary wherein the auxiliary is a sulfuric ester according to  claim 7 .  
     
     
         17 . A method according to  claim 16  wherein the dyeing is carried out with an acid dye, a 1:1 metal complex dye, a 1:2 metal complex dye, a chromium dye, or mixtures thereof.  
     
     
         18 . A method comprising dyeing nitrogenous fiber materials in the presence of an auxiliary wherein the auxiliary is a formulation according to  claim 10 .  
     
     
         19 . A method according to  claim 18  wherein the dyeing is carried out with an acid dye, a 1:1 metal complex dye, a 1:2 metal complex dye, a chromium dye, or mixtures thereof.  
     
     
         20 . A method comprising dyeing nitrogenous fiber materials in the presence of an auxiliary wherein the auxiliary is a formulation according to  claim 12 .  
     
     
         21 . A method according to  claim 20  wherein the dyeing is carried out with an acid dye, a 1:1 metal complex dye, a 1:2 metal complex dye, a chromium dye, or mixtures thereof.