Antioxidant compositions and industrial fluids containing same

• US 6,764,983 B1
• Filed: 07/01/2002
• Issued: 07/20/2004
• Est. Priority Date: 06/29/2001
• Status: Expired due to Fees

• Current Assignee: Iowa State University Research Foundation Incorporated (Iowa State University)
• Original Assignee: Iowa State University Research Foundation Incorporated (Iowa State University)
• Inventors: Hammond, Earl G., Jiang, Yongyi Julia
• Primary Examiner(s): Johnson, Jerry D.
• Application Number:
  US10/187,184
• Time in Patent Office: 750 Days
• Field of Search: 508/403, 508/151, 508/491, 558/52, 558/403
• US Class Current: 508/403
• CPC Class Codes: C07C 309/73 to carbon atoms of non-condensed six-membered aromatic rings
• CPC Class Codes: C10M 135/10 Sulfonic acids or derivatives thereof
• CPC Class Codes: C10M 169/04 Mixtures of base-materials and additives
• CPC Class Codes: C10M 2201/05 Metals; Alloys
• CPC Class Codes: C10M 2201/06 Metal compounds of chromium C10M2201/086
• CPC Class Codes: C10M 2207/401 used as base material
• CPC Class Codes: C10N 2010/02 Groups 1 or 11
• CPC Class Codes: C10N 2030/10 Inhibition of oxidation, e.g. anti-oxidants
• CPC Class Codes: C10N 2040/08 Hydraulic fluids, e.g. brake-fluids

Abstract

The present invention provides new compounds that can be used as antioxidants for either molecules that do not conation ester groups or esters of alcohols that contain two or more ester groups per molecule wherein at least two of the ester groups are on adjacent carbons in the alcohol moiety. Copper ions can enhance the antioxidization activity of the new compounds. Compositions containing one of the new compound and methods of using the new compounds are disclosed.

Claims

1. A composition comprising a compound of the formula:

wherein R₁-R₁₀ are selected from the group consisting of hydrogen and a carbon chain, wherein the carbon chain is saturated, unsaturated, linear, branched, cyclic, or polycyclic and can have heteroatoms attached;

wherein R₁ and R₂ are hydrogen and R₁₀ is a carbon chain of one to 30 carbons when R₁₀ is not hydrogen.

2. The composition of claim 1, wherein R₃-R₉ are selected from hydrogen, an alkyl group, an alkenyl group, an alkynyl group, an alcohol group or an aromatic group wherein each of R₅-R₉ has less than 13 carbons;

and R₁₀ is selected from hydrogen, an alkyl group, an alkenyl group, an alkynyl group and an alcohol group.

3. The composition of claim 1, wherein R₁ and R₃ are hydrogen;

wherein R₄ is selected from the group consisting of hydrogen or and —

CH₂OH, R₁₀ is an alkyl or alkenyl group of 10 to 18 carbons; and

one of R₅-R₉ is hydrogen or an alkyl group of less than 13 carbons and the others are hydrogen.

4. The composition of claim 1 wherein the compound is an ethanediol fatty acylate p-toluenesulfonate.

5. The composition of claim 1, further comprising a copper-containing compound.

6. The composition of claim 5, wherein the copper-containing compound contains a divalent copper.

7. The composition of claim 5, wherein the copper-containing compound is colloidal metallic copper.

21. The composition of claim 8, wherein the compound of claim 1 has a concentration of at least about 100 mM relative to the total volume of the at least one target molecule.

8. A composition comprising:

a fluid comprising at least one target molecule subject to oxidation in the fluid, the at least one target molecule being selected from a non-ester and an alcohol ester having an ester group on each of at least two adjacent carbons in the alcohol moiety; and

a compound of the formula

wherein R₁-R₁₀ are either hydrogen or a carbon chain that can be saturated, unsaturated, linear, branched, cyclic, or polycyclic and can have heteroatoms attached;

the carbon chain of R₁₀ is of one to 30 carbons.

9. The composition of claim 8, wherein the fluid is an unsaturated triglyceride oil.

10. The composition of claim 9 wherein the unsaturated triglyceride oil is a vegetable oil.

11. The composition of claim 10 wherein the vegetable oil is soybean oil.

12. The composition of claim 8, further comprising divalent copper ions.

13. The composition of claim 12, wherein the divalent copper ion has a concentration of at least about 0.001 mM relative to the total volume of the at least one target molecule.

14. The composition of claim 12, wherein the divalent copper ion has a concentration of at least about 0.01 mM relative to the total volume of the at least one target molecule.

15. The composition of claim 12, wherein the divalent copper ion has a concentration of at least about 0.1 mM relative to the total volume of the at least one target molecule.

16. The composition of claim 12, wherein the divalent copper ion has a concentration of at least about 1.0 mM relative to the total volume of the at least one target molecule.

17. The composition of claim 8 wherein the composition is a lubricant.

18. The composition of claim 8 wherein the composition is a hydraulic fluid.

19. The composition of claim 8, wherein the compound has a concentration of at least about 40 mM relative to the total volume of the at least one target molecule.

20. The composition of claim 8, wherein the compound has a concentration of at least about 60 mM relative to the total volume of the at least one target molecule.

22. A method for inhibiting oxidization of a at least one target molecule in a fluid, the at least one target molecule being subject to oxidation in the fluid and being selected from a non-ester and an alcohol ester having an ester group on each of at least two adjacent carbons in the alcohol moiety, the method comprising the step of adding into the fluid a compound of the formula

wherein R₁-R₁₀ are either hydrogen or a carbon chain that can be saturated, unsaturated, linear, branched, cyclic, or polycyclic and can have heteroatoms attached, the carbon chain of R₁₀ is of one to 30 carbons.

23. The method of claim 22 further comprising the step of adding a copper-containing compound into the fluid.

24. A composition comprising a copper-containing compound and a compound of the formula:

wherein R₁-R₁₀ are either hydrogen or a carbon chain that can be saturated, unsaturated, linear, branched, cyclic, or polycyclic and can have heteroatoms attached; and

the carbon chain of R₁₀ is of one to 30 carbons.

25. The composition of claim 24, wherein the copper-containing compound contains a divalent copper.

26. The composition of claim 24, wherein the copper-containing compound is colloidal metallic copper.

27. A compound having a formula

wherein R₁-R₁₀ are either hydrogen or a carbon chain that can be saturated, unsaturated, linear, branched, cyclic, or polycyclic and can have heteroatoms attached;

R₁ and R₂ being hydrogen, R₁₀ being a carbon chain of one to 30 carbons when R₁₀ is not hydrogen.

28. The compound of claim 27, wherein R₃-R₉ are selected from hydrogen, an alkyl group, an alkenyl group, an alkynyl group, an alcohol group or an aromatic group wherein each of R₅-R₉ has less than 13 carbons;

and R₁₀ is selected from hydrogen, an alkyl group, an alkenyl group, an alkynyl group and an alcohol group.

29. The compound of claim 27, wherein R₃ is hydrogen;

wherein R₄ is selected from the group consisting of hydrogen and —

CH₂OH, R₁₀ is an alkyl or alkenyl group of 10 to 18 carbons; and

one of R₅-R₉ is hydrogen or an alkyl group of less than 13 carbons and the others are hydrogen.

30. A fluid comprising:

at least one target molecule subject to oxidation in the fluid and being selected from a non-ester and an alcohol ester having an ester group on each of at least two adjacent carbons in the alcohol moiety; and

a compound of the formula

wherein R₁-R₁₀ are either hydrogen or a carbon chain that can be saturated, unsaturated, linear, branched, cyclic, or polycyclic and can have heteroatoms attached;

the carbon chain of R₁₀ is of one to 30 carbons.

31. The composition of claim 30, the at least one target molecule being an unsaturated triglyceride oil.

32. The composition of claim 31 wherein the unsaturated triglyceride oil is a vegetable oil.

33. The composition of claim 32 wherein the vegetable oil is soybean oil.

34. The composition of claim 30 wherein the composition is a lubricant.

35. The composition of claim 30 wherein the composition is a hydraulic fluid.

36. The composition of claim 30 wherein the compound has a concentration of at least about 40 mM relative to the volume of the at least one target molecule.

37. The composition of claim 30, wherein the compound has a concentration of at least about 60 mM relative to the volume of the at least one target molecule.

38. The composition of claim 30, wherein the compound has a concentration of at least about 100 mM relative to the volume of the at least one target molecule.

39. The composition of claim 30, further comprising divalent copper ions.

40. The composition of claim 39, wherein the divalent copper ions are present at a concentration of at least about 0.001 mM relative to the volume of the at least one target molecule.

41. The composition of claim 39, wherein the divalent copper ions are present at a concentration of at least about 0.01 mM relative to the volume of the at least one target molecule.

42. The composition of claim 39, wherein the divalent copper ions are present at a concentration of at least about 0.1 mM relative to the volume of the at least one target molecule.

43. The composition of claim 39, wherein the divalent copper ions are present at a concentration of at least about 1.0 mM relative to the volume of the at least one target molecule.