Benzo[b]perhydroheterocyclic arylamines and lubricating oil compositions

• US 20070142246A1
• Filed: 12/21/2005
• Published: 06/21/2007
• 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: Chan, Carrie, Cherpeck, Richard
• Granted Patent: US 8,003,583 B2
• Time in Patent Office: Days
• US Class Current: 508/269
• CPC Class Codes: C07D 215/38 Nitrogen atoms nitro radicals C07D215/18
• CPC Class Codes: C07D 215/40 attached in position 8
• CPC Class Codes: C07D 307/79 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
• CPC Class Codes: C07D 319/18 Ethylenedioxybenzenes, not substituted on the hetero ring
• CPC Class Codes: C10M 133/38 Heterocyclic nitrogen compounds
• CPC Class Codes: C10M 133/40 Six-membered ring containing nitrogen and carbon only
• CPC Class Codes: C10M 2215/064 Di- and triaryl amines
• CPC Class Codes: C10M 2215/221 Six-membered rings containing nitrogen and carbon only
• CPC Class Codes: C10M 2215/28 Amides; Imides
• CPC Class Codes: C10M 2219/046 Overbasedsulfonic acid salts
• CPC Class Codes: C10M 2223/045 Metal containing thio derivatives
• CPC Class Codes: C10N 2030/10 Inhibition of oxidation, e.g. anti-oxidants

Abstract

Benzo[b]perhydroheterocyclic arylamine 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:

wherein

R₁ and R₂ are each independently selected from the group consisting of hydrogen, alkyl from 1 to 20 carbon atoms, —

OR, —

SR and —

NRR′

, where R and R′

are independently hydrogen or alkyl from 1 to 6 carbon atoms, or R₁ and R₂ when adjacent to each other together form a 5 to 6 membered alicyclic or aromatic ring which may be optionally substituted with 1 or 2 alkyl groups each having from 1 to 20 carbon atoms;

each R₃ is hydrogen or alkyl from 1 to 6 carbon atoms,

X and X′

are independently selected from —

CHR₄—

, oxygen, sulfur or NR₅, wherein R₄ and R₅ are independently hydrogen or alkyl from 1 to 6 carbon atoms, with the proviso that at least one of X or X′

is a heteroatom positioned ortho or para to the bridging nitrogen atom, and when X or X′

are nitrogen then R₁ or R₂ is not hydroxyl; and

further provided that when one of X or X′

is —

CHR₄—

then the other may not be oxygen; and

n is an integer from 1 to 2.

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

are selected from NR₅ and oxygen.

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

is NR₅.

4. The compound according to claim 3, wherein X is —

CHR₄— and

X′

is NR₅.

5. The compound according to claim 4, wherein n is 2.

6. The compound according to claim 5, wherein R₃, R₄ and R₅ are each hydrogen.

7. The compound according to claim 4, wherein R₁ and R₂ are each independently selected from the group consisting of hydrogen, alkyl from 1 to 20 carbon atoms, or R₁ and R₂ when adjacent to each other together form a 5 to 6 membered alicyclic or aromatic ring which may be optionally substituted with 1 or 2 alkyl groups each having from 1 to 20 carbon atoms.

8. The compound according to claim 7, wherein R₁ and R₂ are each independently selected from the group consisting of hydrogen and alkyl from 1 to 20 carbon atoms.

9. The compound of claim, 1, wherein at least one X and X′

is sulfur.

10. The compound of claim 1, wherein X and X′

are independently selected from oxygen, sulfur or NR₅, wherein R₅ is hydrogen or alkyl from 1 to 6 carbon atoms.

11. The compound of claim 10, wherein X and X′

are oxygen.

12. The compound according to claim 1, wherein R₃ is hydrogen.

13. The compound according to claim 1, wherein R₁ and R₂ are adjacent to each other and together form a 5 to 6 membered aromatic ring which may be optionally substituted with 1 or 2 alkyl groups each having from 1 to 20 carbon atoms.

14. The compound according to claim 1, wherein R₁ is hydrogen and R₂ is selected from the group consisting of alkyl from 1 to 20 carbon atoms, —

OR, —

SR and —

NRR′

, where R and R′

are independently hydrogen or alkyl from 1 to 6 carbon atoms.

15. The compound according to claim 14, wherein R₂ is —

NRR′

where R and R′

are alkyl from 1 to 6.

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

wherein

R₁ and R₂ are each independently selected from the group consisting of hydrogen, alkyl from 1 to 20 carbon atoms, —

OR, —

SR and —

NRR′

, where R and R′

are independently hydrogen or alkyl from 1 to 6 carbon atoms, or R₁ and R₂ when adjacent to each other together form a 5 to 6 membered alicyclic or aromatic ring which may be optionally substituted with 1 or 2 alkyl groups each having from 1 to 20 carbon atoms;

each R₃ is hydrogen or alkyl from 1 to 6 carbon atoms,

X and X′

are independently selected from —

CHR₄—

, oxygen, sulfur or NR₅, wherein R₄ and R₅ are independently hydrogen or alkyl from 1 to 6 carbon atoms, with the proviso that at least one of X or X′

is a heteroatom positioned ortho or para to the bridging nitrogen atom, and when X or X′

are nitrogen then R₁ or R₂ is not hydroxyl; and

further provided that when one of X or X′

is —

CHR₄—

then the other may not be oxygen; and

n is an integer from 1 to 2.

17. The lubricating composition according to claim 16 wherein at least one X and X′

are selected from NR₅ and oxygen.

18. The lubricating composition according to claim 17, wherein at least one X and X′

is NR₅.

19. The lubricating composition according to claim 18, wherein X is —

CHR₄— and

X′

is NR₅.

20. The lubricating composition according to claim 19, wherein n is 2.

21. The lubricating composition according to claim 20, wherein R₃, R₄ and R₅ are each hydrogen.

22. The lubricating composition according to claim 20, wherein R₁ and R₂ are each independently selected from the group consisting of hydrogen, alkyl from 1 to 20 carbon atoms, or R₁ and R₂ when adjacent to each other together form a 5 to 6 membered alicyclic or aromatic ring which may be optionally substituted with 1 or 2 alkyl groups each having from 1 to 20 carbon atoms.

23. The lubricating composition according to claim 22, wherein R₁ and R₂ are each independently selected from the group consisting of hydrogen and alkyl from 1 to 20 carbon atoms.

24. The lubricating composition of claim 16, wherein at least one X and X′

is sulfur.

25. The lubricating composition of claim 16, wherein X and X′

are independently selected from oxygen, sulfur or NR₅, wherein R₅ is hydrogen or alkyl from 1 to 6 carbon atoms.

26. The lubricating composition of claim 25, wherein X and X′

are oxygen.

27. The lubricating composition according to claim 16, wherein R₃ is hydrogen.

28. The lubricating composition according to claim 16, wherein R₁ and R₂ are adjacent to each other and together form a 5 to 6 membered aromatic ring which may be optionally substituted with 1 or 2 alkyl groups each having from 1 to 20 carbon atoms.

29. The lubricating composition according to claim 16, wherein R₁ is hydrogen and R₂ is selected from the group consisting of alkyl from 1 to 20 carbon atoms, —

OR, —

SR and —

NRR′

, where R and R′

are independently hydrogen or alkyl from 1 to 6 carbon atoms.

30. The lubricating composition according to claim 16, wherein R₂ is —

NRR′

where R and R′

are alkyl from 1 to 6.