Azaphenothiazines and azaphenoxazines as antioxidants

Patent metadata

Field	Value
Publication number	US-11512262-B2
Application number	US-201816494936-A
Country	US
Kind code	B2
Filing date	Mar 15, 2018
Priority date	Mar 17, 2017
Publication date	Nov 29, 2022
Grant date	Nov 29, 2022

Abstract

The present disclosure relates generally to antioxidants. More particularly, the present disclosure relates to lubricating compositions comprising an antioxidant.

First claim

What is claimed is:

1. A lubricant composition useful for engines, comprising:
an oil of lubricating viscosity, and
a compound selected from the group consisting of:
a compound of Formula (I):

wherein:
X is CH or N, wherein at least one X is N, and wherein:
(i) Y is O, and A is either H or an electron donating group; wherein said electron donating group is an H atom, a hydrocarbon group, an aryl group, an alkyl group, an alkoxy group, an amine group, a monosubstituted amine, or a disubstituted amine, or
(ii) Y is S and A is either H or an electron donating group, wherein at least one A is an electron donating group when the ring to which it is attached comprises at least one X that is N; and wherein said electron donating group is a hydrocarbon group, an aryl group, an alkyl group, an alkoxy group, an amine group, a monosubstituted amine, or a disubstituted amine;

a compound of Formula (II)

a compound of Formula (IV)

a compound of Formula (VI):

a compound of Formula (VII):

a compound of Formula (VIII):

a compound of Formula (IX):

a compound of Formula (X):

and
a compound of Formula (XI):

2. The lubricant composition of claim 1 , wherein said oil of lubricating viscosity comprises a natural oil, a synthetic oil, or a mixture of a natural oil and a synthetic oil.

3. The lubricant composition of claim 1 , where said oil of lubricating viscosity comprises an API base oil of Group I, Group II, Group III, Group IV, or Group V.

4. The lubricant composition of claim 1 , further comprising an additive.

5. The lubricant composition of claim 4 , wherein said additive comprises one or more of a metal deactivator, a detergent, a friction modifier, an antiwear agent, a rust inhibitor, a dispersant, a viscosity index improver, an extreme pressure agent, an additional antioxidant, a foam inhibitor, a pour point depressant, and a seal swelling agent.

6. A method of forming a lubricant composition useful for engines, comprising combining an oil of lubricating viscosity with a compound selected from the group consisting of:
a compound of Formula (I):

wherein:
X is CH or N, wherein at least one X is N, and wherein:
(i) Y is O, and A is either H or an electron donating group; wherein said electron donating group is an H atom, a hydrocarbon group, an aryl group, an alkyl group, an alkoxy group, an amine group, a monosubstituted amine, or a disubstituted amine, or
(ii) Y is S and A is either H or an electron donating group, wherein at least one A is an electron donating group when the ring to which it is attached comprises at least one X that is N; and wherein said electron donating group is a hydrocarbon group, an aryl group, an alkyl group, an alkoxy group, an amine group, a monosubstituted amine, or a disubstituted amine;
a compound of Formula (II)

a compound of Formula (IV)

a compound of Formula (VI):

a compound of Formula (VII):

a compound of Formula (VIII):

a compound of Formula (IX):

a compound of Formula (X):

and
a compound of Formula (XI):

7. The method of claim 6 , wherein said oil of lubricating viscosity comprises a natural oil, a synthetic oil, or a mixture of a natural oil and a synthetic oil.

8. The method of claim 7 , where said oil of lubricating viscosity comprises an API base oil of Group I, Group II, Group III, Group IV, or Group V.

9. The method of claim 6 , further comprising combining an additive.

10. The method of claim 9 , wherein said additive comprises one or more of a metal deactivator, a detergent, a friction modifier, an antiwear agent, a rust inhibitor, a dispersant, a viscosity index improver, an extreme pressure agent, an additional antioxidant, a foam inhibitors, a pour point depressant, and a seal swelling agent.

11. A kit comprising the lubricant composition of claim 1 .

12. The kit of claim 11 , wherein said oil of lubricating viscosity comprises a natural oil, a synthetic oil, or a mixture of a natural oil and a synthetic oil.

13. The kit of claim 12 , where said oil of lubricating viscosity comprises an API base oil of Group I, Group II, Group III, Group IV, or Group V.

14. The kit of claim 11 , wherein the lubricant composition further comprises an additive.

15. The kit of claim 14 , wherein said additive comprises one or more of a metal deactivator, a viscosity modifier, a detergent, a friction modifier, an antiwear agent, a rust inhibitor, a corrosion inhibitor, a dispersant, a dispersant viscosity modifier, a viscosity index improver, an extreme pressure agent, an additional antioxidant, and a foam inhibitor.

16. A method of lubricating a combustion engine comprising applying a lubricant composition comprising an oil of lubricating viscosity and a compound selected from the group consisting of:
a compound of Formula (I):

wherein:
X is CH or N, wherein at least one X is N, and wherein:
(i) Y is O, and A is either H or an electron donating group; wherein said electron donating group is an H atom, a hydrocarbon group, an aryl group, an alkyl group, an alkoxy group, an amine group, a monosubstituted amine, or a disubstituted amine, or
(ii) Y is S and A is either H or an electron donating group, wherein at least one A is an electron donating group when the ring to which it is attached comprises at least one X that is N; and wherein said electron donating group is a hydrocarbon group, an aryl group, an alkyl group, an alkoxy group, an amine group, a monosubstituted amine, or a disubstituted amine;
a compound

Assignees

• Univ Ottawa

Inventors

• Pratt Derek Andrew
• Haidasz Evan

Classifications

• C10M2219/104

  containing sulfur and carbon with nitrogen or oxygen in the ring · CPC title

• C10M2203/003

  used as base material · CPC title

• C07D513/04

  Ortho-condensed systems · CPC title

• C10M135/36

  the ring containing sulfur and carbon with nitrogen or oxygen · CPC title

• C10M133/48 Primary

  the ring containing both nitrogen and oxygen · CPC title