2-substituted imidazole and benzimidazole corrosion inhibitors

Patent metadata

Field	Value
Publication number	US-10202694-B2
Application number	US-201615166527-A
Country	US
Kind code	B2
Filing date	May 27, 2016
Priority date	May 28, 2015
Publication date	Feb 12, 2019
Grant date	Feb 12, 2019

Abstract

Disclosed are methods of using nitrogen-containing compounds as corrosion inhibitors. The present method is used to inhibit corrosion of a metal surface in contact with an aqueous system using 2-substituted imidazoles and 2-substituted benzimidazoles, and provides enhanced protection against corrosion of metals in the aqueous system. The method comprises the use of corrosion inhibitors that are generally resistant to halogen attack and provide good corrosion resistance in the presence of oxidizing halogen-based biocides. Formulations comprising 2-substituted imidazoles and 2-substituted benzimidazoles are also disclosed.

First claim

The invention claimed is:

1. A method for inhibiting corrosion of a metal surface in contact with an aqueous system comprising:
adding to the aqueous system a compound of formula (I),
wherein each X 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;
Y is selected from the group consisting of hydroxyl, halogen, oxo, alkoxy, thiol, alkylthio, amino, hydrogen, and aminoalkyl;
Z is selected from the group consisting of carbon and nitrogen;
R 1 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;
R 2 and R 3 are selected from the group consisting of hydrogen, halogen, hydroxyl, aryl, phenyl, heteroaryl, benzyl, alkylheteroaryl, carbonyl, C 2 -C 16 alkenyl, C 2 -C 16 alkynyl, C 3 -C 8 cycloalkyl, and C 1 -C 16 alkyl; and
m is 1, 2, 3, or 4; or
a salt thereof;
and the aqueous system comprises an oxidizing halogen compound and has a pH of from about 6 to about 12.

2. The method of claim 1 , wherein Z is carbon.

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

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

wherein Me is methyl.

5. The method of claim 1 , wherein the metal surface comprises copper or a copper alloy.

6. The method of claim 1 , wherein the aqueous system is a cooling water system.

7. The method of claim 1 , wherein the metal has a corrosion rate of less than about 0.1 mpy.

8. The method of claim 1 , wherein the aqueous system has a pH of from about 7 to about 12.

9. A method for inhibiting corrosion of a metal surface in contact with an aqueous system comprising an oxidizing halogen compound, the method comprising adding to the aqueous system a compound of formula (II),
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;
R 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, 3, or 4; or
a salt thereof;
and the aqueous system has a pH of from about 6 to about 12.

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

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

wherein Me is methyl.

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

13. The method of claim 9 , wherein the compound of formula (II) is

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

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

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

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

18. A formulation for inhibiting corrosion of a metal surface in contact with an aqueous system comprising an oxidizing halogen compound and having a pH of from about 6 to about 12, the formulation comprising a compound of formula (I) or (II), a phosphoric acid, and a phosphinosuccinic oligomer;
wherein formula (I) is

wherein each X 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;
Y is selected from the group consisting of hydroxyl, halogen, oxo, alkoxy, thiol, alkylthio, amino, hydrogen, and aminoalkyl;
Z is selected from the group consisting of carbon and nitrogen;
R 1 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;
R 2 and R 3 are selected from the group consisting of hydrogen, halogen, hydroxyl, aryl, phenyl, heteroaryl, benzyl, alkylheteroaryl, carbonyl, C 2 -C 16 alkenyl, C 2 -C 16 alkynyl, C 3 -C 8 cycloalkyl, and C 1 -C 16 alkyl; and
m is 1, 2, 3, or 4; or

a salt thereof;
formula (II) is

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;
R 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; or
n is 1, 2, 3, or 4; or

a salt thereof.

19. The formulation of claim 18 , wherein the formulation further comprises a fluorescent organic compound.

20. The formulation of claim 19 , wherein the fluorescent organic compound is selected from the group consisting of Rhodamine, a derivative of Rhodamine, an acridine dye, fluorescein, a derivative of fluorescein, and combinations thereof.

Assignees

• Ecolab Usa Inc

Inventors

• Rane Deepak
• Seetharaman Jothibasu
• Atkins Jeffery M
• Harbindu Anand
• Anant Piyush
• Sivaswamy Vaideeswaran
• Cheruku Pradeep

Classifications

• C07D235/12

  Radicals substituted by oxygen atoms · CPC title

• C23F11/149 Primary

  Heterocyclic compounds containing nitrogen as hetero atom · CPC title

• C07D401/04

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

• C07D231/12

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C02F2303/08

  Corrosion inhibition · CPC title