Dibenzo[b]perhydroheterocyclic amines and lubricating oil compositions

• US 7,285,518 B2
• Filed: 12/21/2005
• Issued: 10/23/2007
• Est. Priority Date: 12/21/2005
• Status: Active Grant

• Current Assignee: Chevron Oronite Company LLC (Chevron Corp.)
• Original Assignee: Chevron Oronite Company LLC (Chevron Corp.)
• Inventors: Cherpeck, Richard E., Chan, Carrie Y.
• Primary Examiner(s): Saeed; Kamal A.
• Assistant Examiner(s): Cheng; Karen
• Application Number:
  US11/316,099
• Publication Number:
  US 20070142245A1
• Time in Patent Office: 671 Days
• Field of Search: 546/112, 548/159, 548/217, 548/305.1, 549/434, 549/462, 508/266, 508/269, 508/270, 508/271
• US Class Current: 508/266
• CPC Class Codes: C07D 215/40 attached in position 8
• CPC Class Codes: C07D 307/82 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
• CPC Class Codes: C07D 317/66 Nitrogen atoms not forming part of a nitro radical

Abstract

Dibenzo[b]perhydroheterocyclic amine compounds have shown to be particularly useful as stabilizers. The compounds may serve as antioxidants, antiozoants, heat stabilizers and ultraviolet light stabilizers and such compounds are oil soluble, thus particularly suited for use as an antioxidant in a lubricating oil composition.

Claims

1. A compound according to formula I:

2. The compound according to claim 1, wherein at least one of X and X′

is oxygen or NR₄, where R₄ is hydrogen or alkyl from 1 to 6 carbon atoms.

3. The compound according to claim 2, wherein each R₂ is hydrogen.

4. The compound according to claim 2, wherein at least one of X and X′

is —

CHR₃—

where R₃ is hydrogen or alkyl from 1 to 6 carbon atoms.

5. The compound according to claim 4, wherein R₃ is hydrogen.

6. The compound according to claim 2, wherein at least one of Y and Y′

are oxygen or NR₆, where R₆ is hydrogen or alkyl from 1 to 6 carbon atoms.

7. The compound according to claim 6, wherein each R₁ is hydrogen.

8. The compound according to claim 6, wherein at least one Y and Y′

is —

CHR₅—

where R₅ is hydrogen or alkyl from 1 to 6 carbon atoms.

9. The compound according to claim 8, wherein R₅ is hydrogen.

10. The compound according to claim 1, wherein m=n.

11. The compound according to claim 10, wherein m is one.

12. The compound according to claim 11, wherein X and Y are oxygen.

13. The compound according to claim 12, wherein X′

and Y′

are independently selected from oxygen and —

CH₂—

.

14. The compound according to claim 13, wherein X′

and Y′

are —

CH₂—

.

15. The compound according to claim 1, wherein X and X′

are independently selected from —

CHR₃— and

NR₄ wherein R₃ and R₄ are independently hydrogen or alkyl from 1 to 6 carbon atoms.

16. The compound according to claim 15, wherein m=n.

17. The compound according to claim 16, wherein m is two.

18. The compound according to claim 17, wherein Y and Y′

are independently selected from —

CHR₅— and

NR₆ wherein R₅ and R₆ are independently hydrogen or alkyl from 1 to 6 carbon atoms.

19. The compound according to claim 18, wherein R₃, R₄, R₅ and R₆ are hydrogen.

20. The compound according to claim 1, wherein the compound comprises unsubstituted and alkyl substituted dibenzoperhydroheterocylic amines of Formula I selected from the group consisting of:

N-quinolin-8- ylquinolin-6-amine;

N-(1,2,3,4-tetrahydroquinolin-8-yl)-1,2,3,4-tetrahydroquinolin-6-amine;

N-(2,3-dihydro-1-benzofuran-5-yl)-2,3-dihydro-1-benzofuran-5-amine;

N-1,3-benzodioxol-5-yl-1,3-benzodioxol-5-amine and alkyl substituted derivatives thereof.

22. A lubricating oil composition comprising an oil of lubricating viscosity and a compound according to claim 20.

21. A lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor amount of the compound according to formula I: