Dithiocarbamate derivatives and lubricants containing same

• US 5,686,397 A
• Filed: 02/03/1997
• Issued: 11/11/1997
• Est. Priority Date: 02/03/1997
• Status: Expired due to Term

• Current Assignee: Uniroyal Chemical Company Inc (Lanxess AG)
• Original Assignee: Uniroyal Chemical Company Inc (Lanxess AG)
• Inventors: Migdal, Cyril A., Baranski, John R.
• Primary Examiner(s): Johnson, Jerry D.
• Application Number:
  US08/794,112
• Time in Patent Office: 281 Days
• Field of Search: 508/274, 548/142
• US Class Current: 508/274
• CPC Class Codes: C07D 285/16 Thiadiazines; Hydrogenated thiadiazines
• CPC Class Codes: C10M 135/36 the ring containing sulfur and carbon with nitrogen or oxygen
• CPC Class Codes: C10M 2219/10 Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
• CPC Class Codes: C10M 2219/102 containing sulfur and carbon only in the ring
• CPC Class Codes: C10M 2219/104 containing sulfur and carbon with nitrogen or oxygen in the ring
• CPC Class Codes: C10M 2219/106 Thiadiazoles
• CPC Class Codes: C10N 2040/02 Bearings
• CPC Class Codes: C10N 2040/08 Hydraulic fluids, e.g. brake-fluids
• CPC Class Codes: C10N 2040/135 Steam engines or turbines
• CPC Class Codes: C10N 2040/20 Metal working
• CPC Class Codes: C10N 2040/25 Internal-combustion engines
• CPC Class Codes: C10N 2040/251 Alcohol-fuelled engines
• CPC Class Codes: C10N 2040/255 Gasoline engines
• CPC Class Codes: C10N 2040/28 Rotary engines

Abstract

A composition of matter is disclosed having the structure: ##STR1## wherein R and R¹ are independently a member selected from the group consisting of alkyl, cycloalkyl, aryl, aralkyl, and alkaryl; R² is an alkylene moiety; R³ is hydrogen, alkyl, alkenyl, aryl, alkaryl, aralkyl, or 2-hydroxyalkyl; X is sulfur; and y is 0 or 1. Lubricants and lubricant additives comprising the composition are also disclosed. The lubricants are preferably lubricating oils.

Claims

1. A composition of matter having the structure:

##STR7## wherein R and R¹ are independently a member selected from the group consisting of alkyl, cycloalkyl, aryl, aralkyl, and alkaryl;

R² is an alkylene moiety;

R³ is hydrogen, alkyl, alkenyl, aryl, alkaryl, aralkyl, or 2-hydroxyalkyl;

X is sulfur; and

y is 0 or 1.

2. The composition of claim 1 wherein R is alkyl.

3. The composition of claim 2 wherein R¹ is alkyl.

4. The composition of claim 3 wherein R² is a lower alkylene group of three to ten carbon atoms.

5. The composition of claim 4 wherein y is 0 and R³ is hydrogen.

6. The composition of claim 3 wherein R² is isopropylene.

7. The composition of claim 6 wherein y is 0 and R³ is hydrogen.

8. The composition of claim 3 wherein y is 0 and R³ is hydrogen.

9. The composition of claim 1 wherein R is tetradecyl.

10. The composition of claim 9 wherein R¹ is tetradecyl.

11. The composition of claim 10 wherein R² is a lower alkylene group of three to ten carbon atoms.

12. The composition of claim 11 wherein y is 0 and R³ is hydrogen.

13. The composition of claim 10 wherein R² is isopropylene.

14. The composition of claim 10 wherein y is 0 and R³ is hydrogen.

15. The composition of claim 1 wherein R² is a lower alkylene group of one to twelve carbon atoms.

16. The composition of claim 15 wherein y is 0 and R³ is hydrogen.

17. The composition of claim 1 wherein R² is isopropylene.

18. The composition of claim 17 wherein y is 0 and R³ is hydrogen.

19. The composition of claim 1 wherein y is 0 and R³ is hydrogen.

20. 1{propyl-2-(S-{mercaptothioliazoylthio})}-N,N-di(tetradecyl)dithiocarbamate.

21. A lubricant additive comprising a composition of matter having the structure:

##STR8## wherein R and R¹ are independently a member selected from the group consisting of alkyl, cycloalkyl, aryl, aralkyl, and alkaryl;

R² is an alkylene moiety;

R³ is hydrogen, alkyl, alkenyl, aryl, alkaryl, aralkyl, or 2-hydroxyalkyl;

X is sulfur; and

y is 0 or 1.

22. The additive of claim 21 wherein the additive is a lubricating oil additive.

23. The additive of claim 21 wherein R is alkyl.

24. The additive of claim 23 wherein R¹ is alkyl.

25. The additive of claim 24 wherein R² is isopropylene.

26. The additive of claim 25 wherein y is 0 and R³ is hydrogen.

27. The additive of claim 24 wherein R² is a lower alkylene group of three to ten carbon atoms.

28. The additive of claim 27 wherein y is 0 and R³ is hydrogen.

29. The additive of claim 24 wherein y is 0 and R³ is hydrogen.

30. The additive of claim 21 wherein R is tetradecyl.

31. The additive of claim 30 wherein R¹ is tetradecyl.

32. The additive of claim 31 wherein R² is a lower alkylene group of three to ten carbon atoms.

33. The additive of claim 32 wherein y is 0 and R³ is hydrogen.

34. The additive of claim 31 wherein R² is isopropylene.

35. The additive of claim 31 wherein y is 0 and R³ is hydrogen.

36. The additive of claim 21 wherein R² is a lower alkylene group of three to ten carbon atoms.

37. The additive of claim 36 wherein y is 0 and R³ is hydrogen.

38. The additive of claim 21 wherein R² is isopropylene.

39. The additive of claim 38 wherein y is 0 and R³ is hydrogen.

40. The additive of claim 21 wherein y is 0 and R³ is hydrogen.

41. The additive of claim 21 wherein said additive is 1{propyl-2-(S-{mercaptothioliazoylthio})}-N,N-di(tetradecyl)dithiocarbamate.

42. A lubricant comprising a lubricant additive comprising a composition of matter having the structure:

##STR9## wherein R and R¹ are independently a member selected from the group consisting of alkyl, cycloalkyl, aryl, aralkyl, and alkaryl;

R² is an alkylene moiety;

R³ is hydrogen, alkyl, alkenyl, aryl, alkaryl, aralkyl, or 2-hydroxyalkyl;

X is sulfur; and

y is 0 or 1.

43. The lubricant of claim 42 wherein said lubricant is a lubricating oil.

44. The lubricant of claim 42 wherein R is alkyl.

45. The lubricant of claim 44 wherein R¹ is alkyl.

46. The lubricant of claim 45 wherein R² is a lower alkylene group of three to ten carbon atoms.

47. The lubricant of claim 46 wherein y is 0 and R³ is hydrogen.

48. The lubricant of claim 45 wherein R² is isopropylene.

49. The lubricant of claim 48 wherein y is 0 and R³ is hydrogen.

50. The lubricant of claim 45 wherein y is 0 and R³ is hydrogen.

51. The lubricant of claim 42 wherein R is tetradecyl.

52. The lubricant of claim 51 wherein R¹ is tetradecyl.

53. The lubricant of claim 52 wherein R² is a lower alkylene group of three to ten carbon atoms.

54. The lubricant of claim 53 wherein y is 0 and R³ is hydrogen.

55. The lubricant of claim 52 wherein R² is isopropylene.

56. The lubricant of claim 52 wherein y is 0 and R³ is hydrogen.

57. The lubricant of claim 42 wherein R² is a lower alkylene group of three to ten carbon atoms.

58. The lubricant of claim 57 wherein y is 0 and R³ is hydrogen.

59. The lubricant of claim 42 wherein R² is isopropylene.

60. The lubricant of claim 59 wherein y is 0 and R³ is hydrogen.

61. The lubricant of claim 42 wherein y is 0 and R³ is hydrogen.

62. The lubricant of claim 42 wherein the additive is 1{propyl-2-(S-{mercaptothioliazoylthio})}-N,N-di(tetradecyl)dithiocarbamate.