Nitrogen containing surfactants with alkoxylation on the hydroxyl group of fatty chains

1. An agricultural composition comprising at least one agricultural chemical and at least one nitrogen containing surfactant composition, wherein the agricultural chemical is an herbicide and the nitrogen containing surfactant composition comprises at least one nitrogen containing surfactant of structure (i):

wherein

p is 1-3;

R 0 is nothing or C1-C6 alkylene;

R 1 and R 2 each independently are C1-18 hydrocarbons, saturated or unsaturated, linear or branched alkyl or alkylene groups so that the total hydrocarbon chain length is C14 to C22;

A is a C2-C3 alkylene;

x′ is 0-100;

y′ is 0 or 1;

Z is a H (hydrogen) when y′=0, a C1-C22 alkyl when y′=1, or a polyalkylene oxide (A′O) w′ H when y′=1 where A′ is a C2-C3 alkylene and w′ is 0-100;

R 3 is H, CH 3 , or (A′″O) w ″H where A′″ is a C2-C3 alkylene and w″=1-100;

R 5 , R 7 , and R 9 are the same or different and are selected from nothing, H, CH 3 , CH 3 CH 2 , (A″O) w H where A″ is a C2-C3 alkylene and w=1-100, O (oxygen), CH 2 —COO, CH 2 —COO − M + , CH 2 —CH 2 —COO − M + , CH 2 —CH 2 —CH 2 —SO 3 , or CH 2 —CH(OH)—CH 2 —SO 3 ;

q=1-5;

R 8 is C2-C3 alkylene;

X − is an anion and e is a value that balances the charge in the molecule when N is a quaternary nitrogen; and M + is a suitable cation; or

at least one nitrogen containing surfactant of structure (h):

wherein p is 1-3; R 0 is nothing or C1-C6 alkylene; R 1 and R 2 each independently are C1-C18 hydrocarbons, saturated or unsaturated, linear or branched alkyl or alkylene groups so that the total hydrocarbon chain length is C14 to C22; A is a C2-C3 alkylene; x′ is 0-100; Z is C1-C22 alkyl or a polyalkylene oxide (A′O) w ′H where A′ is a C2-C3 alkylene and w′ is 0-100; R 4 , R 5 , R 6 , R 7 , and R 9 are the same or different and are selected from nothing, H, CH 3 , CH 3 CH 2 , (A″O) w H where A″ is a C2-C3 alkylene and w=1-100, O (oxygen), CH 2 —COO, CH 2 —COO − M + , CH 2 —CH 2 —COO − M + , CH 2 —CH 2 —CH 2 —SO 3 , or CH 2 —CH(OH)—CH 2 —SO 3 ; q=0-5; R 8 is C2-C3 alkylene; X″ is an anion and e is a value that balances the charge in the molecule when N is a quaternary nitrogen; and M + is a suitable cation; or

at least one nitrogen containing surfactant of structure (j):

wherein p is 1-3; R 0 is nothing or C1-C6 alkylene;

R 1 and R 2 each independently are C1-C18 hydrocarbons, saturated or unsaturated, linear or branched alkyl or alkylene groups so that the total hydrocarbon chain length is C14 to C22; A is a C2-C3 alkylene; x′ is 0-100; y′ is 0 or 1; Z is a H (hydrogen) when y′=0, a C1-C22 alkyl when y′=1, or a polyalkylene oxide (A′O) w ′H when y′=1 where A′ is a C2-C3 alkylene and w′ is 0-100; R 3 and R 9 each is H, CH 3 , or (A′″O) w ″H where A′″ is a C2-C3 alkylene and w″=1-100; wherein the concentration of the at least one nitrogen containing surfactant composition is present in the agricultural composition at a level of greater than 0.001 wt %.

2. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (i):

wherein R3 is H; R 5 and R 7 are each CH 3 ; R 9 is selected from nothing, H, CH 3 , CH 3 CH 2 , O (oxygen), CH 2 —COO and CH 2 —COO − M + ; q=1; and R 8 is propylene.

3. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (i) wherein q=1, R 3 is H, R 8 is C3 (propylene), R 5 and R 7 is each CH 3 , R 9 is nothing, and e is zero.

4. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (i) wherein q=1, R 3 is H, R 8 is C3 (propylene), R 5 and R 7 is each CH 3 , R 9 is O (oxygen), and e is zero.

5. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (i) wherein q=1, R 3 is H, R 8 is C3 (propylene), R 5 and R 7 is each CH 3 , R 9 is CH 2 —COO, and e is zero.

6. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (i) wherein q=1, R 3 is H, R 8 is C3 (propylene), R 5 and R 7 is each CH 3 , R 9 is methyl (or ethyl), e is 1, and X is chloride or sulfate.

7. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (i) wherein q=1, R 3 is H, R 8 is C2 (ethylene), R 5 is H, R 7 is (A″O) w H where w=1, R 9 is nothing, and e is zero.

8. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (i) wherein q=1, R 3 is H or (A′″O) w ″H where w″=1-100, R 8 is C2 (ethylene), R 7 and R 5 are each (A″O) w H where w=1-100; R 9 is nothing; and e is zero.

9. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (i) wherein q=1, R 3 is H or (A′″O) w ″H where w″=1-100; R 8 is C2 (ethylene); R 7 and R 5 are each (A″O) w H where w=1-100; R 9 is O (oxygen); and e is zero.

10. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (i) wherein q=1, R 3 is H or (A′″O) w ″H where w=1-100; R 8 is C2 (ethylene); R 7 and R 5 are each (A″O) w H where w=1-100; R 9 is methyl or ethyl; e is 1; and X is chloride or sulfate.

11. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (i) wherein q=2; R 3 is H or (A′″O) w ″H where w=1-100; R 8 is C2 (ethylene); R 5 is nothing, H, or (A″O) w H where w=1-100; R 7 is H or (A″O) w H where w=1-100, R 9 is nothing, and e is zero.

12. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (i) wherein q=2; R 3 is H or (A′″O) w ″H where w″=1-100; R 8 is C2 (ethylene); R 5 is nothing or O (oxygen); R 7 is (A″O) w H where w=1-100; R 9 is nothing or O (oxygen); and e is zero.

13. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (i) wherein q=2; R 3 is H or (A′″O) w ″H where w″=1-100; R 8 is C2 (ethylene); R 5 is nothing or CH 3 ; R 7 is (A″O) w H where w=1-100; R 9 is nothing or CH 3 or ethyl; e is 1 or >1; and X is chloride or sulfate.

14. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (h) wherein q=0, R 4 and R 6 are each methyl, R 9 is nothing, and e is zero.

15. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (h) wherein q=0, R 4 and R 6 are each methyl, R 9 is CH 2 —COO, and e is zero.

16. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (h) wherein q=0, R 4 and R 6 are each methyl, R 9 is O (oxygen), and e is zero.

17. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (h) wherein q=0, R 4 and R 6 are each methyl, R 9 is methyl (or ethyl), e is 1, and X is chloride (or sulfate).

18. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (h) wherein q=0, R 4 and R 6 are each (A″O) w H where w=1-100; R 9 is nothing; and e is zero.

19. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (h) wherein q=0, R 4 and R 6 are each (A″O) w H where w=1-100; R 9 is O (oxygen); and e is zero.

20. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (h) wherein q=0, R 4 and R 6 are each (A″O) w H where w=1-100; R 9 is methyl (or ethyl); e is 1; and X is chloride or sulfate.

21. An agricultural composition according to claim 1 comprising the nitrogen containing surfactant of structure (h) wherein q=0, R 4 and R 6 are each methyl or (A″O) w H where w=1, R 9 is CH 2 —COO, and e is zero.

22. The agricultural composition of claim 1 wherein the concentration of the at least one nitrogen containing surfactant is greater than 1 wt %.

23. The agricultural composition of claim 1 wherein the concentration of the at least one nitrogen containing surfactant is greater than 10 wt %.

24. The agricultural composition of claim 1 wherein the concentration of the at least one nitrogen containing surfactant is greater than 30 wt %.

25. The agricultural composition of claim 1 wherein the concentration of the at least one nitrogen containing surfactant is greater than 50 wt %.

26. The agricultural composition of claim 1 wherein the herbicide is glyphosate.

27. The agricultural composition of claim 1 wherein the herbicide is dicamba.

28. The agricultural composition of claim 1 wherein the herbicide is 2,4-D.

29. The agricultural composition of claim 1 wherein the herbicide is glufosinate.

30. The agricultural composition of claim 26 wherein the agricultural composition further comprises a C5-C12 dimethylamidopropylamine.

31. A nitrogen containing surfactant of structure (h):

wherein p is 1-3; R 0 is nothing or C1-C6 alkylene; R 1 and R 2 each independently are C1-C18 hydrocarbons, saturated or unsaturated, linear or branched alkyl or alkylene groups so that the total hydrocarbon chain length is C14 to C22; A is a C2-C3 alkylene; x′ is 0-100; Z is C1-C22 alkyl or a polyalkylene oxide (A′O) w ′H where A′ is a C2-C3 alkylene and w′ is 0-100; R 4 , R 5 , R 6 , R 7 , and R 9 are the same or different and are selected from nothing, H, CH 3 , CH 3 CH 2 , (A″O) w H where A″ is a C2-C3 alkylene and w=1-100, O (oxygen), CH 2 —COO, CH 2 —COO − M + , CH 2 —CH 2 —COO − M + , CH 2 —CH 2 —CH 2 —SO 3 , or CH 2 —CH(OH)—CH 2 —SO 3 ; q=0-5; R 8 is C2-C3 alkylene; X − is an anion and e is a value that balances the charge in the molecule when N is a quaternary nitrogen; and M + is a suitable cation.

32. A method of making a nitrogen containing surfactant of structure (h) as defined in any one of claims 31 and 14 - 21 , the method comprising the steps of:

reacting unsaturated fatty acid with ammonium to produce a fatty nitrile;

epoxidizing the fatty nitrile;

opening the ring of the epoxidized fatty amine to produce a nitrile with di-pendant groups;

alkoxylating the nitrile with di-pendant groups;

optionally further alkoxylating the alkoxylated nitrile with di-pendant groups; and

reducing the alkoxylated nitrile with di-pendant groups.

33. A method of claim 32 wherein the alkoxylation up to 7 or fewer polyalkylene oxide group is done with a Lewis acid catalyst on the fatty acid, fatty ester, triglycerides with at least one pendant OH group.

34. A method of claim 33 wherein the further alkoxylation is done with an alkaline catalyst.

35. A agricultural composition according to claim 1 wherein w′ and w″ of structure (j) is 1-50.

36. A agricultural composition according to claim 1 wherein w′ and w″ of structure (j) is 5-20.