Organic activator

Abstract

This invention relates to organic activators having the following formula: wherein Z is a charge equalizing ion and one or more of the moieties R 1 , R 2 , R 3 , R 4 and R 5 are modified such that the one or more of the drawbacks associated with this class of molecule are essentially eliminated, cleaning compositions comprising such activators; and processes for making and using such activators and cleaning products.

1 . A compound having the formula:  
     
       
         
         
             
             
         
       
     
     wherein 
 a.) R 4  and R 5  are independently hydrogen, or substituted or unsubstituted alkyl, alkenyl or aryl groups containing from 1 to 18 carbon atoms;  
 b.) at least one of R 1 , R 2  or R 3  is a hydroxyalkyl moiety comprising at least 2 carbon atoms;  
 c.) any remaining R 1 , R 2  or R 3  moieties are independently substituted or unsubstituted alkyl, alkenyl or aryl groups containing from 1 to 18 carbon atoms; and  
 d.) X is a charge-equalizing anion.  
 
   
   
       2 . A compound according to  claim 1  wherein at least one of R 1 , R 2  or R 3  is a hydroxyalkyl moiety comprising at least 2 carbon atoms and all of said hydroxyalkyl moieties' hydroxyl groups are separated from said compound's quaternary nitrogen by at least 2 carbon atoms.  
   
   
       3 . A compound according to  claim 2  wherein all of said hydroxyalkyl moieties' hydroxyl groups are separated from said compound's quaternary nitrogen by at least 3 carbon atoms.  
   
   
       4 . A compound according to  claim 1  wherein at least one of R 1 , R 2  or R 3  is a linear hydroxyalkyl moiety comprising from 2 to 12 carbons.  
   
   
       5 . A compound according to  claim 4  wherein at least one of R 1 , R 2  or R 3  is a linear hydroxyalkyl moiety comprising from 3 to 12 carbons and all of said linear hydroxyalkyl moieties' hydroxyl groups are separated from said compound's quaternary nitrogen by at least 2 carbon atoms.  
   
   
       6 . A compound having the formula:  
     
       
         
         
             
             
         
       
     
     wherein 
 a.) R 4  and R 5  are independently hydrogen, or substituted or unsubstituted alkyl, alkenyl or aryl groups containing from 1 to 18 carbon atoms;  
 b.) at least one of R 1 , R 2  or R 3  is a moiety selected from the group consisting of R 6 OSO 2   − , R 6 OSO 3   − , R 6 OPO 2   − , R 6 OCO 2   − , R 6 SO 2   − , R 6 SO 3   − , and R 6 CO 2   − ; wherein R 6  is independently a C 1  to C 20  substituted or unsubstituted alkyl; provided that when one or more of R 1 , R 2  or R 3  is R 6 CO 2   − ; the CO 2   −  group of any R 6 C02- moiety is separated from said compound's quaternary nitrogen by at least 2 carbon atoms;  
 c.) any remaining R 1 , R 2  or R 3  moieties are independently substituted or unsubstituted alkyl, alkenyl or aryl groups containing from 1 to 18 carbon atoms; and  
 d.) M, when present, is a charge balancing cation.  
 
   
   
       7 . A compound according to  claim 6  wherein only one of R 1 , R 2  or R 3  is a moiety selected from the group consisting of R 6 OSO 2   − , R 6 OSO 3   − , R 6 OPO 2   − , R60CO 2   − , R 6 SO 2   − , R 6 SO 3   − , and R 6 CO 2   − .  
   
   
       8 . A compound having the formula:  
     
       
         
         
             
             
         
       
     
     wherein 
 a.) R 1 , R 2  and R 3  are independently selected from the group consisting of substituted or unsubstituted C 1  to C 20  alkyl moieties;  
 b.) R 4  and R 5  are independently selected from the group consisting of hydrogen, or substituted or unsubstituted C 1  to C 20  alkyl moieties, provided R 4  and R 5  are not both hydrogen;  
 c.) at least one of R 1 , R 2  or R 3  is joined with at least one of R 4  and R 5  to form a ring comprising at least 5 atoms, one of said atoms being the quaternary nitrogen of said compound; and  
 d.) X is a charge-equalizing anion.  
 
   
   
       9 . A compound according to  claim 8  wherein only one of R 1 , R 2 , or R 3 is joined with only one of R 4  or R 5  to form a ring comprising at least 5 atoms, one of said atoms being the quaternary nitrogen of said compound.  
   
   
       10 . A process of making a bleach activator having the formula:  
     
       
         
         
             
             
         
       
     
     wherein R 4  and R 5  are independently hydrogen, or substituted or unsubstituted alkyl, alkenyl or aryl groups containing from 1 to 18 carbon atoms; at least one of R 1 , R 2  or R 3  is a hydroxyalkyl moiety comprising at least 2 carbon atoms; any remaining R 1 , R 2  or R 3  moieties are independently substituted or unsubstituted alkyl, alkenyl or aryl groups containing from 1 to 18 carbon atoms; and X is a charge-equalizing anion said process comprising the steps of: 
 a.) reacting an amine having the formula  
                     
  wherein R 1 , R 2  and R 3  are as defined above, with an acetonitrile derivative having the formula:  
                     
  wherein R 4  and R 5  are as defined above and Y is a moiety that upon displacement by the amine becomes X as defined above; or  
 b.) reacting an amine having the formula:  
                     
  wherein R 1 , R 3 , R 4  and R 5  are as defined above, with a compound having the formula: 
   R 2 —Y 
 wherein R 2  is as defined above and Y is a moiety that upon displacement by the amine becomes X as defined above.  
 
   
   
       11 . A process of making a zwitterionic bleach activator said activator comprising only one anionic moiety and only one quaternary nitrogen, said activator having the formula:  
     
       
         
         
             
             
         
       
     
     wherein R 4  and R 5  are independently hydrogen, or substituted or unsubstituted alkyl, alkenyl or aryl groups containing from 1 to 18 carbon atoms; only one of R 1 , R 2  or R 3 is a moiety selected from the group consisting of R 6 OSO 2   − , R 6 OSO 3   − , R 6 OPO2 − , R 6 OCO 2   − , R 6 SO 2   − , R 6 SO 3   − , and R 6 CO 2   − ; wherein R 6  is independently a C 1  to C 20  substituted or unsubstituted alkyl; provided that when R 1 , R 2  or R 3 is R 6 CO 2   − ; the CO 2   −  group of the R 6 CO 2   −  moiety is separated from said compound's quaternary nitrogen by at least 2 carbon atoms; and the remaining R 1 , R 2  or R 3  moieties are independently substituted or unsubstituted alkyl, alkenyl or aryl groups containing from 1 to 18 carbon atoms, said process comprising the steps of reacting an amine having the formula:  
     
       
         
         
             
             
         
       
     
     wherein R 1 , R 3 , R 4  and R 5  are as defined above, with a compound having the formula: 
       R 2 —Y 
     wherein R 2  is a moiety selected from the group consisting of R 6 OSO 2   − M, R 6 OSO 3   − M, R 6 OPO 2   − M, R 6 OCO 2   − M, R 6 SO 2   − M, R 6 SO 3   − M, and R 6 CO 2   − M wherein M is a charge neutralizing cation and Y is moiety that upon displacement by the amine becomes a charge neutralizing anion which when combined with M forms an acid or a salt; or  
     
       
         
         
             
             
         
       
     
     wherein R 6  is C 1  to C 20  substituted or unsubstituted alkylene and G is selected from the group consisting of OSO 2 , OSO 3 , OPO 2 , OCO 2 , S(O)O, SO 3  and CO 2 .  
   
   
       12 . A process of making a bleach activator having the formula:  
     
       
         
         
             
             
         
       
     
     wherein R 1 , R 2  and R 3  are independently selected from the group consisting of substituted or unsubstituted C 1  to C 20  alkyl moieties; R 4  and R 5  are independently selected from the group consisting of hydrogen, or substituted or unsubstituted C 1  to C 20  alkyl moieties, provided that R 4  and R 5  are not both hydrogen; at least one of R 1 , R 2  or R 3 is joined with at least one of R 4  and R 5  to form a ring comprising at least 5 atoms, one of said atoms being the quaternary nitrogen of said compound; and X, when present, is a charge-equalizing anion, said process comprising the steps of reacting an amine having the formula:  
     
       
         
         
             
             
         
       
     
     wherein R 8 , R 9 , R 10  and R 11  are independently selected from the group consisting of substituted or unsubstituted C 1  to C 20  alkyl moieties; and at least one of R 8  or R 10  is joined with at least one of R 9  or R 11  to form a ring comprising at least 5 atoms, one of said atoms being the nitrogen of said amine; with a compound selected from the group consisting of: 
       R 2 —Y 
     wherein R 2  is as defined above and Y is moiety that upon displacement by the amine becomes X as defined above; or  
     
       
         
         
             
             
         
       
     
     wherein R 6  is C 1  to C 20  substituted or unsubstituted alkylene and G is selected from the group consisting of OSO 2 , OSO 3 , OPO 2 , OCO 2 , SO 2 , SO 3  and CO 2 .  
   
   
       13 . A cleaning composition comprising a bleach activator according to  claim 1 .  
   
   
       14 . A cleaning composition according to  claim 13  comprising a lipophilic fluid.  
   
   
       15 . A cleaning composition comprising a bleach activator according to  claim 6 .  
   
   
       16 . A cleaning composition according to  claim 15  comprising a lipophilic fluid.  
   
   
       17 . A cleaning composition comprising a bleach activator according to  claim 8 .  
   
   
       18 . A cleaning composition according to  claim 17  comprising a lipophilic fluid.  
   
   
       19 . A method of cleaning a substrate comprising contacting said substrate with a bleach activator or a cleaning composition comprising said bleach activator, said activator being selected from the group consisting of: 
 a.) a compound having the formula:                           wherein 
 (i) R 4  and R 5  are independently hydrogen, or substituted or unsubstituted alkyl, alkenyl or aryl groups containing from 1 to 18 carbon atoms;  
 (ii) at least one of R 1 , R 2  or R 3  is a hydroxyalkyl moiety comprising at least 2 carbon atoms;  
 (iii) any remaining R 1 , R 2  or R 3  moieties are independently substituted or unsubstituted alkyl, alkenyl or aryl groups containing from 1 to 18 carbon atoms; and  
 (iv) X is a charge-equalizing anion;  
   b.) a compound having the formula:                           wherein 
 (i) R 4  and R 5  are independently hydrogen, or substituted or unsubstituted alkyl, alkenyl or aryl groups containing from 1 to 18 carbon atoms;  
 (ii) at least one of R 1 , R 2  or R 3  is a moiety selected from the group consisting of R 6 OSO 2   − , R 6 OSO 3   − , R 6 OPO 2   − , R 6 OCO 2   − , R 6 SO 2   − , R 6 SO 3   − , and R 6 CO 2   − ; wherein R 6  is independently a C 1  to C 20  substituted or unsubstituted alkyl; provided that when one or more of R 1 , R 2  or R 3  is R 6 CO 2   − ; the CO 2   −  group of any R 6 CO 2   −  moiety is separated from said compound's quaternary nitrogen by at least 2 carbon atoms;  
 (iii) any remaining R 1 , R 2  or R 3  moieties are independently substituted or unsubstituted alkyl, alkenyl or aryl groups containing from 1 to 18 carbon atoms; and  
 (iv) M, when present, is a charge balancing cation;  
   c.) a compound having the formula:                           wherein 
 (i) R 1 , R 2  and R 3  are independently selected from the group consisting of substituted or unsubstituted C 1  to C 20  alkyl moieties;  
 (ii) R 4  and R 5  are independently selected from the group consisting of hydrogen, or substituted or unsubstituted C 1  to C 20  alkyl moieties, provided R 4  and R 5  are not both hydrogen;  
 (iii) at least one of R 1 , R 2  or R 3  is joined with at least one of R 4  and R 5  to form a ring comprising at least 5 atoms, one of said atoms being the quaternary nitrogen of said compound; and  
 (iv) X is a charge-equalizing anion; and  
   d.) mixtures thereof;    said method including the optional steps of washing, rinsing, or washing and then rinsing said substrate.