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

Patent metadata

Field	Value
Publication number	US-10000437-B2
Application number	US-201414770524-A
Country	US
Kind code	B2
Filing date	Mar 13, 2014
Priority date	Mar 14, 2013
Publication date	Jun 19, 2018
Grant date	Jun 19, 2018

Abstract

The present invention is directed to a nitrogen containing surfactant composition comprising at least one nitrogen containing surfactant of structure (h) or structure (i). The nitrogen containing surfactant of structure (h) is as shown below: Structure (h). The nitrogen containing surfactant of structure (i) is as shown below: Structure (i). The present invention is also directed to an agricultural composition comprising at least one agrochemical and at least one nitrogen containing surfactant composition of the present invention.

First claim

We claim:

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 c

Assignees

• Akzo Nobel Chemicals Int Bv

Inventors

• Zhu Shawn
• Su Biing-Ming
• Nguyen Giao Vinh
• Schwarzmayr Louis
• Sun Jinxia Susan
• Wang Xiaoyu
• Band Elliot Isaac
• Islam Mojahedul
• Puglisi Christine
• Winkenwerder Wyatt
• Davis Charles Woodville

Classifications

• C07C51/02

  from salts of carboxylic acids · CPC title

• C07C235/10

  having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups · CPC title

• A01N39/04

  Aryloxy-acetic acids; Derivatives thereof · CPC title

• C11D1/42

  Amino alcohols or amino ethers · CPC title

• C11D1/44

  Ethers of polyoxyalkylenes with amino alcohols; Condensation products of epoxyalkanes with amines · CPC title