Alkoxylated polyalkylene imines or alkoxylated polyamines with improved biodegradability

Abstract

Described herein is an alkoxylated polyalkylene imine or an alkoxylated polyamine according to the general formula (I)Also described herein is a process for preparing such alkoxylated polyalkylene imines or alkoxylated polyamines as well as a method of using such compounds within, for example, cleaning compositions and/or in fabric and home care products. Also described herein are compositions or products that include the alkoxylated polyalkylene imine or the alkoxylated polyamine.

1 . An alkoxylated polyalkylene imine or an alkoxylated polyamine of the general formula (I) 
       
         
           
           
               
               
           
         
         in which the variables are each defined as follows: 
         R represents identical or different, i) linear or branched C 2 -C 12 -alkylene radicals or ii) an etheralkyl unit of the following formula (III): 
       
       
         
           
           
               
               
           
         
         
           in which the variables are each defined as follows:
 R 10 , R 11 , R 12  represent identical or different, linear or branched C 2 -C 6 -alkylene radicals and 
 d is an integer having a value in a range of 0 to 50 or 
 iii) C 5 -C 10 -cycloalkylene radicals optionally substituted with at least one C 1 -C 3 -alkyl; 
 
         
         B represents a continuation of the alkoxylated polyalkylene imine by branching; 
         y and z are each an integer having a value in a range of 0 to 150, under the provisio that both z and y are 0 in case R are C 5 -C 10 -cycloalkylene radicals optionally substituted with at least one C 1 -C 3 -alkyl; 
         E1, E2 and E4 represent an identical or different residue according to formula (IIa) or an identical or different residue according to formula (IIb),
 wherein the residue according to formula (IIa) is an alkylenoxy unit defined as follows 
 
       
       
         
           
           
               
               
           
         
         
           in which the variables are each defined as follows: 
           R 1  represents C 2 -C 22 -(1,2-alkylene) radicals; 
           R 2  represents hydrogen and/or C 1 -C 22 -alkyl and/or C 7 -C 22 -aralkyl in case z is an integer ≥1 within general formula (I), or 
           R 2  represents hydrogen and/or C 1 -C 4 -alkyl and/or C 7 -C 22 -aralkyl in case z is 0 within general formula (I); 
           R 3  represents linear or branched C 1 -C 22 -alkylene radicals; 
           m is an integer having a value of 1 to 10; 
           n is an integer having a value of 5 to 100; 
           and wherein the residue according to formula (IIb) is an alkylenoxy unit defined as follows 
         
       
       
         
           
           
               
               
           
         
         
           in which the variables are defined as follows: 
           R l  represents C 2 -C 22 -(1,2-alkylene) radicals; 
           R 2  represents hydrogen and/or C 1 -C 22 -alkyl and/or C 7 -C 22 -aralkyl; 
           n is an integer having a value of 5 to 100; 
         
         E3 is hydrogen in case E2 is a residue according to formula (IIa) or E3 is a residue according to formula (IIb); 
         E5 is hydrogen in case E4 is a residue according to formula (IIa) or E5 is a residue according to formula (IIb); 
         wherein 20 to 100% of a total amount of E2 and E4 is a residue according to formula (IIa) and 50 to 100% of a total amount of E1 is a residue according to formula (IIb). 
       
     
     
         2 . The alkoxylated polyalkylene imine or alkoxylated polyamine according to  claim 1 , wherein R represents identical or different,
 i) linear or branched C 2 -C 12 -alkylene radicals, or   ii) C 5 -C 10 -cycloalkylene radicals optionally substituted with at least one C 1 -C 3 -alkyl.   
     
     
         3 . The alkoxylated polyalkylene imine or the alkoxylated polyamine according to  claim 1 , wherein within formulas (IIa) and/or (IIb) the variables are each defined as follows:
 R 1  represents 1,2-ethylene, 1,2-propylene or 1,2-butylene; and/or   R 2  represents hydrogen and/or C 1 -C 4 -alkyl; and/or   R 3  represents linear or branched C 2 -C 10 -alkylene radicals; and/or   m is an integer having a value in a range of 1 to 5; and/or   n is an integer having a value in a range of 8 to 40; and/or   50 to 100% of the total amount of E2 and E4 is a residue according to formula (IIa) and 80 to 100% of the total amount of E1 is a residue according to formula (IIb).   
     
     
         4 . The alkoxylated polyalkylene imine or the alkoxylated polyamine according to  claim 1 , wherein a weight average molecular weight (Mw) of a polyalkylene imine backbone or of a polyamine backbone lies in a range of 50 to 10 000 g/mol. 
     
     
         5 . The alkoxylated polyalkylene imine according to  claim 1 , wherein the variables are each defined as follows:
 R is ethylene or propylene;   the sum of y+z is an integer having a value in a range of 9 to 120.   
     
     
         6 . The alkoxylated polyalkylene imine according to  claim 5 , wherein
 R is ethylene or propylene;   the sum of y+z is an integer having a value in the range of 9 to 120;   R 1  represents 1,2-ethylene;   R 2  represents hydrogen and/or C 1 -C 4 -alkyl;   R 3  represents linear or branched C 2 -C 10 -alkylene radicals;   m is an integer having a value in a range of 1 to 5;   n is an integer having a value in a range of 8 to 40;   50 to 100% of the total amount of E2 and E4 is a residue according to formula (IIa) and 80 to 100% of the total amount of E1 is a residue according to formula (IIb).   
     
     
         7 . The alkoxylated polyalkylene imine according to  claim 5 , wherein the variables are each defined as follows:
 R is ethylene;   the sum of y+z is an integer having a value in a range of 10 to 20;   R 1  represents 1,2-ethylene;   R 2  represents hydrogen;   R 3  represents linear or branched C 2 -C 5 -alkylene radicals;   m is an integer having a value in a range of 1 to 3;   n is an integer having a value in a range of 10 to 25;   wherein 90 to 100% of the total amount of E2 and E4 is a residue according to formula (IIa) and 85 to 95% of the total amount of E1 is a residue according to formula (IIb).   
     
     
         8 . The alkoxylated polyamine according to  claim 1 , wherein
 y is an integer having a value in a range of 0 to 10;   z is 0;   R represents identical or different, linear or branched C 2 -C 12 -alkylene radicals or an etheralkyl unit according to formula (III), wherein
 d is from 1 to 5, and 
 R 10 , R 11 , R 12  are independently selected from the group consisting of linear or branched C3 to C4 alkylene radicals. 
   
     
     
         9 . The alkoxylated polyamine according to  claim 8 , wherein
 R 1  represents 1,2-ethylene;   R 2  represents hydrogen and/or C 1 -C 4 -alkyl;   R 3  represents linear or branched C 2 -C 10 -alkylene radicals;   m is an integer having a value in a range of 1 to 5;   n is an integer having a value in the range of 8 to 40;   y is an integer having a value in the range of 1 to 10;   wherein 50 to 100% of the total amount of E2 and E4 is a residue according to formula (IIa) and 80 to 100% of the total amount of E1 is a residue according to formula (IIb).   
     
     
         10 . The alkoxylated polyamine according to  claim 8 , wherein
 R is ethylene or propylene;   R 1  represents 1,2-ethylene;   R 2  represents hydrogen;   R 3  represents linear or branched C 2 -C 5 -alkylene radicals;   m is an integer having a value in a range of 1 to 3;   n is an integer having a value in a range of 10 to 25;   y is an integer having a value in a range of 2 to 4;   wherein 90 to 100% of the total amount of E2 and E4 is a residue according to formula (IIa) and 90 to 100% of the total amount of E1 is a residue according to formula (IIb).   
     
     
         11 . The alkoxylated polyamine according to  claim 1 , wherein
 y is 0;   z is 0; and   R represents identical or different C 5 -C 10 -cycloalkylene radicals optionally substituted with at least one C 1 -C 3 -alkyl.   
     
     
         12 . The alkoxylated polyalkylene imine or the alkoxylated polyamine according to  claim 1 , wherein up to 100% of nitrogen atoms present in the alkoxylated polyalkylene imine or the alkoxylated polyamine are quaternized 
     
     
         13 . A method of using the alkoxylated polyalkylene imine or the alkoxylated polyamine according to  claim 1 , the method comprising: using the alkoxylated polyalkylene imine or the alkoxylated polyamine in laundry detergents, in cleaning compositions, in fabric and home care products, in cosmetic formulations, as crude oil emulsion breaker, in pigment dispersions for ink jet inks, in formulations for electro plating, in cementitious compositions and/or as dispersant for agrochemical formulations. 
     
     
         14 . A process for preparing the alkoxylated polyalkylene imine or the alkoxylated polyamine according to  claim 1 , wherein a polyalkylene imine backbone or a polyamine backbone is first reacted with at least one lactone and/or at least one hydroxy carbon acid and then with at least one C 2 -C 22 -epoxide in order to obtain the respective alkoxylated compounds. 
     
     
         15 . The process according to  claim 14  wherein, per mol of N—H functionalities in the polyalkylene imine or the polyamine, the respective polyalkylene imine backbone or polyamine backbone is reacted with at least 0.05 moles of at least one lactone and/or at least one hydroxy carbon acid and then with at least 5 moles of least one C 2 -C 22 -epoxide. 
     
     
         16 . The process according to  claim 14 , wherein the alkoxylated polyalkylene imine or the alkoxylated polyamine is additionally quaternized. 
     
     
         17 . The process according to  claim 14 , wherein the lactone is caprolactone, the hydroxy carbon acid is lactic acid and/or the C 2 -C 22 -epoxide is ethylene oxide. 
     
     
         18 . A laundry detergent, a cleaning composition, a fabric and home care product, a cosmetic formulation, a crude oil emulsion breaker, a pigment dispersion for ink jet inks, a formulation for electro plating, a cementitious composition and/or a dispersant for agrochemical formulations, comprising at least one alkoxylated polyalkylene imine or alkoxylated polyamine according to  claim 1 . 
     
     
         19 . The alkoxylated polyamine according to  claim 1 , wherein
 y is 0;   z is 0; and   R is at least one C 6 -C 7 -cycloalkylene radical substituted with at least one methyl or ethyl.   
     
     
         20 . The alkoxylated polyalkylene imine or the alkoxylated polyamine according to  claim 1 , wherein up to 100% of nitrogen atoms present in the alkoxylated polyalkylene imine or the alkoxylated polyamine are quaternized, and wherein the degree of quaternization of the nitrogen atoms present in the alkoxylated polyalkylene imine or the alkoxylated polyamine lies in a range of 10% to 95%.