Phosphorous-containing compounds and uses thereof

Patent metadata

Field	Value
Publication number	US-9944879-B2
Application number	US-201514681507-A
Country	US
Kind code	B2
Filing date	Apr 8, 2015
Priority date	Oct 8, 2014
Publication date	Apr 17, 2018
Grant date	Apr 17, 2018

Abstract

The present invention provides phosphorous-containing compounds useful as antiwear additive components, lubricant additive compositions and lubricant compositions each comprising such compounds, and methods for making and using the same.

First claim

The invention claimed is:

1. A compound of Formula (I)

wherein each R 1 is independently alkyl or cycloalkyl;
each R 2 R 3 , R 4 and R 5 is independently selected from the group consisting of hydrogen, alkyl and cycloalkyl;
each n is independently an integer from 0 to 6;
M 1 , M 2 , X 1 , and X 2 are each independently S or O;
each W is independently S or O;
Y is selected from the group consisting of alkyl, alkoxyalkylene, benzyl, and —R 6 —R 7 —R 8 ;
R 6 is alkylene;
R 7 is selected from the group consisting of a bond, alkylene; —C(O)— and —C(R 9 )—;
R 8 is selected from the group consisting of alkyl, hydroxyalkylene, hydroxyalkyleneoxy, hydroxyl and alkoxy; and
R 9 is alkyl.

2. The compound of claim 1 , wherein X 1 is S.

3. The compound of claim 1 , wherein X 2 is S.

4. The compound of claim 1 , wherein M 1 is S.

5. The compound of claim 1 , wherein M 2 is S.

6. The compound of claim 1 , wherein X 1 , X 2 , M 1 , and M 2 are each S.

7. The compound of claim 1 , wherein X 1 is O.

8. The compound of claim 1 , wherein X 2 is O.

9. The compound of claim 1 , wherein M 1 is O.

10. The compound of claim 1 , wherein M 2 is O.

11. The compound of claim 1 , wherein X 1 , X 2 , M 1 , and M 2 are each O.

12. The compound of claim 1 , wherein X 1 and X 2 are O and M 1 and M 2 are S.

13. The compound of claim 1 , wherein X 1 and X 2 are S and M 1 and M 2 are O.

14. The compound of claim 1 , selected from the group consisting of

wherein each R 1 is independently alkyl or cycloalkyl;
each R 2 R 3 , R 4 and R 5 is independently selected from the group consisting of hydrogen, alkyl and cycloalkyl;
each n is independently an integer from 0 to 6;
Y is selected from the group consisting of alkyl, alkoxyalkylene, benzyl, and —R 6 —R 7 —R 8 ;
R 6 is alkylene;
R 7 is selected from the group consisting of a bond, alkylene; —C(O)— and —C(R 9 )—;
R 8 is selected from the group consisting of alkyl, hydroxyalkylene, hydroxyalkyleneoxy, hydroxyl and alkoxy; and
R 9 is alkyl.

15. The compound of claim 1 , wherein each R 2 R 3 , R 4 and R 5 is independently selected from hydrogen or C 1 -C 30 alkyl.

16. The compound of claim 1 , wherein at least one of R 2 and R 3 is hydrogen and at least one of R 4 and R 5 is hydrogen.

17. The compound of claim 1 , wherein each R 1 is the same.

18. The compound of claim 1 , wherein Y is O 1 —C 20 alkyl.

19. The compound of claim 1 , wherein Y is —R 6 —R 7 —R 8 .

20. The compound of claim 1 , wherein R 3 and R 4 are the same.

21. The compound of claim 1 , wherein R 2 and R 5 are the same.

22. The compound of claim 1 , wherein R 2 and R 4 are the same.

23. The compound of claim 1 , wherein R 3 and R 5 are the same.

24. The compound of claim 1 , wherein R 2 and R 5 are both hydrogen.

25. The compound of claim 1 , wherein R 1 is C 3 -C 10 alkyl.

26. The compound of claim 25 , wherein R 1 is C 3 -C 6 alkyl.

27. The compound of claim 1 , wherein one of R 2 and R 3 and one of R 4 and R 5 is C 1 -C 10 alkyl.

28. The compound of claim 1 , wherein the compound is selected from the group consisting of:

29. The compound of claim 1 , wherein the compound is selected from the group consisting of:

30. The compound of claim 1 , wherein the compound is selected from the group consisting of:

31. The compound of claim 1 , wherein the compound is selected from the group consisting of:

32. A compound prepared by reacting a compound of the formula:

with a reactive group to form a compound of the structure

wherein each W is independently S or O;
M 1 , M 2 , X 1 , and X 2 are each independently S or O;
each R 1 is independently alkyl or cycloalkyl;
each R 2 R 3 , R 4 and R 5 is independently selected from the group consisting of hydrogen, alkyl and cycloalkyl;
each n is independently an integer from 0 to 6;
Y is selected from the group consisting of alkyl, alkoxyalkylene, benzyl, and —R 6 —R 7 —R 8 ;
R 6 is alkylene;
R 7 is selected from the group consisting of a bond, alkylene; —C(O)— and —C(R 9 )—;
R 8 is selected from the group consisting of alkyl, hydroxyalkylene, hydroxyalkyleneoxy, hydroxyl and alkoxy; and
R 9 is alkyl.

33. A compound prepared by a process comprising:
(a) reacting a compound of the formula:

with an epoxide of the formula

wherein R is alkyl or cycloalkyl; and
M and X are each independently S or O;

(b) reacting the reaction product of step (a) with P 2 W 5 , to form a compound of the structure

and
(c) reacting the reaction product of step (b) with a reactive group to form a compound of the structure

wherein each W is the same and is either S or O;
each R 1 is independently alkyl or cycloalkyl;
each R 2 R 3 , R 4 and R 5 is independently selected from the group consisting of hydrogen, alkyl and cycloalkyl;
n is 0;
Y is selected from the group consisting of alkyl, alkoxyalkylene, benzyl, and —R 6 —R 7 —R 8 ;
R 6 is alkylene;
R 7 is selected from the group consisting of a bond, alkylene; —C(O)— and —C(R 9 )—;
R 8 is selected from the group consisting of alkyl, hydroxyalkylene, hydroxyalkyleneoxy, hydroxyl and alkoxy; and
R 9 is hydroxyl.

34. A lubricant additive composition comprising a compound of claim 1 .

35. The lubric

Assignees

• Afton Chemical Corp

Inventors

• Edwards David
• Parks Bevin

Classifications

• C10N2030/06

  Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure · CPC title

• C10N2040/25

  Internal-combustion engines · CPC title

• C07F9/16

  Esters of thiophosphoric acids or thiophosphorous acids · CPC title

• C10M2223/047

  Thioderivatives not containing metallic elements · CPC title

• C10M2223/04

  Phosphate esters · CPC title