Corrosion inhibitors

Patent metadata

Field	Value
Publication number	US-10190222-B2
Application number	US-201615166511-A
Country	US
Kind code	B2
Filing date	May 27, 2016
Priority date	May 28, 2015
Publication date	Jan 29, 2019
Grant date	Jan 29, 2019

Abstract

Disclosed are novel compounds and methods useful in applications relating to industrial water systems. The compounds of the present invention are nitrogen-containing heterocyclic compounds comprising a benzotriazole covalently bonded to a benzimidazole moiety, and provide enhanced protection against corrosion of metals in aqueous systems. The compounds of the present invention are generally resistant to halogen attack and provide good corrosion resistance in the presence of oxidizing halogen-based biocides.

First claim

The invention claimed is:

1. A compound of formula (I):

wherein each of X and Y is the same or different, and is selected from the group consisting of hydrogen, C 1 -C 16 alkyl, aryl, C 2 -C 16 alkenyl, C 2 -C 16 alkynyl, heteroaryl, C 3 -C 8 cycloalkyl, benzyl, alkylheteroaryl, halogen, halosubstituted alkyl, amino, aminoalkyl, cyano, alkoxy, hydroxyl, thiol, alkylthio, carbonyl, nitro, phosphoryl, phosphonyl, and sulfonyl;
each of R 1 and R 2 is the same or different, and is selected from the group consisting of hydrogen, deuterium, C 1 -C 16 alkyl, aryl, C 2 -C 16 alkenyl, C 2 -C 16 alkynyl, heteroaryl, C 3 -C 8 cycloalkyl, benzyl, alkylheteroaryl, halogen, hydroxyl, and carbonyl;
m is 1, 2, 3, or 4; and
n is 1, 2, or 3;
or a salt thereof.

2. The compound of claim 1 , wherein R 1 and R 2 are hydrogen.

3. The compound of claim 1 , wherein X and Y are hydrogen.

4. The compound of claim 1 , wherein X is C 1 -C 16 alkyl, Y is hydrogen, m is 1, and n is 1.

5. The compound of claim 1 , wherein the compound of formula (I) is

6. The compound of claim 1 , wherein the compound of formula (I) is

wherein Me is methyl.

7. The compound of claim 1 , wherein the compound of formula (I) is

8. The compound of claim 1 , wherein the compound of formula (I) is

wherein Me is methyl.

9. A method for inhibiting corrosion of a metal surface in contact with an aqueous system, the method comprising adding to the aqueous system a compound of formula (I),

wherein each of X and Y is the same or different, and is selected from the group consisting of hydrogen, C 1 -C 16 alkyl, aryl, C 2 -C 16 alkenyl, C 2 -C 16 alkynyl, heteroaryl, C 3 -C 8 cycloalkyl, benzyl, alkylheteroaryl, halogen, halosubstituted alkyl, amino, aminoalkyl, cyano, alkoxy, hydroxyl, thiol, alkylthio, carbonyl, nitro, phosphoryl, phosphonyl, and sulfonyl;
each of R 1 and R 2 is the same or different, and is selected from the group consisting of hydrogen, deuterium, C 1 -C 16 alkyl, aryl, C 2 -C 16 alkenyl, C 2 -C 16 alkynyl, heteroaryl, C 3 -C 8 cycloalkyl, benzyl, alkylheteroaryl, halogen, hydroxyl, and carbonyl;
m is 1, 2, 3, or 4; and
n is 1, 2, or 3;
or a salt thereof.

10. The method of claim 9 , wherein the compound of formula (I) is

11. The method of claim 9 , wherein the compound of formula (I) is

wherein Me is methyl.

12. The method of claim 9 , wherein the compound of formula (I) is

13. The method of claim 9 , wherein the metal surface comprises copper or a copper alloy.

14. The method of claim 9 , wherein the aqueous system comprises an oxidizing halogen compound.

15. The method of claim 9 , wherein the compound of formula (I) is added to the aqueous system at a dosage of from about 0.01 ppm to about 100 ppm.

16. The method of claim 9 , wherein the aqueous system has a pH of from about 6 to about 12.

17. The method of claim 9 , wherein the aqueous system is a cooling water system.

18. The method of claim 17 , wherein the cooling water system is a closed loop cooling water system.

19. The method of claim 17 , wherein the cooling water system is an open loop cooling water system.

20. The method of claim 9 , wherein the metal has a corrosion rate of about 0.1 mpy or less.

Assignees

• Ecolab Usa Inc

Inventors

• Seetharaman Jothibasu
• Johnson Donald A
• Harbindu Anand
• Rane Deepak
• Atkins Jeffery M
• Mondkar Hemant
• Sivaswamy Vaideeswaran

Classifications

• C23F11/149 Primary

  Heterocyclic compounds containing nitrogen as hetero atom · CPC title

• C07D403/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C02F5/125

  combined with inorganic substances · CPC title

• C02F2303/08

  Corrosion inhibition · CPC title

• C02F2103/023

  Water in cooling circuits · CPC title