Dispersing agent

Patent metadata

Field	Value
Publication number	US-11753541-B2
Application number	US-202017425291-A
Country	US
Kind code	B2
Filing date	Jan 13, 2020
Priority date	Jan 23, 2019
Publication date	Sep 12, 2023
Grant date	Sep 12, 2023

Abstract

The invention relates to compositions containing compounds of formula (I), formula (II), or mixtures thereof, in which n is an integer greater than or equal to 1, R 1 , an aliphatic, linear or branched hydrocarbon group having 1 to 10 carbon atoms, a hydrogen atom, the structural unit —O—X, or the structural unit —CH 2 —O—X, X corresponds to formula (III), in which a is an integer from 2 to 6, b is an integer from 0 to 3, c is an integer from 20 to 28, m is 1 or 2, R 2 is an aliphatic, linear or branched hydrocarbon group having 1 to 10 carbon atoms, Y is hydrogen, —SO 3 M, —SO 2 M, —PO 3 M 2 , or —CH 2 COOM, and M is a cation. The compounds of formula (I), of formula (II), or mixtures thereof are preferably suitable to act as a dispersing agent.

First claim

The invention claimed is:

1. A composition containing compounds of formula (I), formula (II), or mixtures thereof,

wherein
n is an integer greater than or equal to 1
R 1 is an aliphatic, linear or branched hydrocarbon radical having 1 to 10 carbon atoms, a hydrogen atom, the structural unit —O—X, or the structural unit —CH 2 —O—X,
X corresponds to formula (III)

in which
a is an integer from 2 to 6,
b is an integer from 0 to 3,
c is an integer from 20 to 28,
m is 1 or 2,
R 2 is an aliphatic, linear or branched hydrocarbon radical having 1 to 10 carbon atoms,
Y is hydrogen, —SO 3 M, —SO 2 M, —PO 3 M 2 or —CH 2 COOM, and
M is a cation.

2. The composition as claimed in claim 1 , wherein in formula III, read from left to right, block m is before block c, and wherein blocks a and b are arranged within m in a random or blockwise manner.

3. The composition as claimed in claim 1 , wherein a is 3, 4 or 5.

4. The composition as claimed in claim 1 , wherein b is an integer from 0 to 2.

5. The composition as claimed in claim 1 , wherein m is equal to 1.

6. The composition as claimed in claim 1 , wherein Y is H or —PO 3 M 2 .

7. The composition as claimed in claim 1 , wherein the ratio of (a+b):c is 1:4 to 1:6.

8. The composition as claimed in claim 1 , wherein
a is a number from 2 to 6,
b is a number from 0 to 3,
c is a number from 20 to 28,
m is 1 or 2, and
Y is H or —PO 3 M 2 .

9. The composition as claimed in claim 1 , wherein a is a number from 2 to 6, b is zero or 1, m is equal to one, and c is a number from 20 to 28.

10. The composition as claimed in claim 1 , wherein R 1 is —CH 2 —O—X.

11. The composition as claimed in claim 1 , wherein R 2 is —CH 3 .

12. The composition as claimed in claim 1 , wherein n is 1.

13. A process for preparing compounds of formula (I), formula (II), or mixtures thereof,

wherein
n is an integer greater than or equal to 1 R 1 is an aliphatic, linear or branched hydrocarbon radical having 1 to 10 carbon atoms, a hydrogen atom, the structural unit —O—X, or the structural unit —CH 2 —O—X,
X corresponds to formula (III)

in which
a is an integer from 2 to 6,
b is an integer from 0 to 3,
c is an integer from 20 to 28,
m is 1 or 2,
R 2 is an aliphatic, linear or branched hydrocarbon radical having 1 to 10 carbon atoms,
Y is hydrogen, —SO 3 M, —SO 2 M, —PO 3 M 2 or —CH 2 COOM, and
M is a cation,
by
1. providing an alcohol resulting from formula I or formula II by formal replacement of the X radical with H,
2. alkoxylating the alcohol with, per active hydrogen atom, 2 to 6 mol of styrene oxide and optionally with up to 3 mol of a C 3 - to C 12 -alkylene oxide, wherein the alkoxylation can be effected simultaneously with styrene oxide and the C 3 - to C 32 -alkylene oxide or sequentially,
3. optionally repeating step 2 once or twice, and
4. alkoxylating the product thus obtained with 20 to 28 mol of ethylene oxide per active hydrogen atom.

14. The process as claimed in claim 13 , wherein the alkoylating is conducted using alkali metal, alkaline-earth metal or double metal cyanide catalysts.

15. The process as claimed in claim 13 , wherein the alkoylating is conducted at temperatures in the range from 130-140° C. and at a pressure of from 2 to 9 bar.

16. The process as claimed in claim 13 , wherein an alkali, alkaline earth or double metal cyanide catalyst is present in the alkoylating step, and wherein the catalyst is neutralized at the end of reaction.

17. The process as claimed in claim 13 , further comprising the step of modifying the product obtained by adduct formation with an anionic group Y, wherein Y is selected from the group consisting of —SO 3 M, —SO 2 M, —PO 3 M 2 and —CH 2 COOM.

18. The process as claimed in claim 13 , further comprising the step after the end of reaction, wherein the product obtained is mixed with an aqueous substance and neutralized with lactic acid.

19. The process as claimed in claim 13 , wherein a is a number from 2 to 6, b is zero or 1, m is equal to 1, and c is a number from 20 to 28.

20. The process as claimed in claim 13 , wherein Y is PO 3 M 2 .

21. A dispersing agent for aqueous formulations of crop protection agent, comprising at least one compound of formula (I), formula (II), or mixtures thereof,

wherein
n is an integer greater than or equal to 1
R 1 is an aliphatic, linear or branched hydrocarbon radical having 1 to 10 carbon atoms, a hydrogen atom, the structural unit —O—X, or the structural unit —CH 2 —O—X,
X corresponds to formula (III)

in which
a is an integer from 2 to 6,
b is an integer from 0 to 3,
c is an integer from 20 to 28,
m is 1 or 2,
R 2 is an aliphatic, linear or branched hydrocarbon radical having 1 to 10 carbon atoms,
Y is hydrogen, —SO 3 M, —SO 2 M, —PO 3 M 2 or —CH 2 COOM, and
M is a cation.

Assignees

• Clariant Int Ltd

Inventors

• Gabel Dorothee
• Hövelmann Felix
• Kupfer Rainer
• Scheinhardt Benjamin
• Beck Dietmar

Classifications

• C08G65/2609 Primary

  containing aliphatic hydroxyl groups · CPC title

• C08L71/02 Primary

  Polyalkylene oxides · CPC title

• C08G65/331

  containing oxygen {(cyclic ether compounds C08G65/26)} · CPC title

• C08G65/3355

  having phosphorus bound to carbon and oxygen · CPC title

• C08G2650/30

  branched · CPC title