Cyclen friction modifiers for boundary lubrication

Patent metadata

Field	Value
Publication number	US-10081776-B2
Application number	US-201615152284-A
Country	US
Kind code	B2
Filing date	May 11, 2016
Priority date	May 11, 2015
Publication date	Sep 25, 2018
Grant date	Sep 25, 2018

Abstract

Compositions comprising one or more cyclen compounds which can be structurally modified to affect anti-friction and anti-wear functionality.

First claim

We claim:

1. A composition comprising an oil component and a component comprising at least one cyclen compound of a formula

wherein each of R 1 , nR 2 , R 3 and R 4 (R 1 -R 4 ) is a moiety independently selected from about C 5 - about C 24 linear, substituted linear, branched and substituted branched alkyl moieties, where said substituents are selected from oxa (—O—), aza (—NH— or —N—), aryl, carbonyl, alkylcarbonyl, arylcarbonyl, oxycarbonyl (—OC(O)—), alkoxycarbonyl, amido (—NHC(O)—), alkylcarboxamido, arylcarboxamido, hydroxy, alkoxy, aryloxy, amino, alkylamino, arylamino, heteroaryl, heteroarylalkyl and heteroaryloxy substituents and combinations thereof; and n is an integer selected from 0- about 10.

2. The composition of claim 1 wherein each of R 1 -R 4 is a C 10 -C 20 alkyl moiety.

3. The composition of claim 2 wherein at least R 1 is a C 11 alkyl moiety.

4. The composition of claim 3 wherein each of R 1 -R 4 is independently a linear C 11 -C 18 alkyl moiety.

5. The composition of claim 4 wherein each of R 1 -R 4 is a linear, unsubstituted C 11 alkyl moiety.

6. The composition of claim 5 wherein n is 1-3.

7. The composition of claim 1 wherein said oil component is selected from base oils and formulated commercially-available motor oils.

8. The composition of claim 7 wherein said cyclen component is about 0.1 wt. % to about 1.0 wt. % of said composition.

9. The composition of claim 1 wherein said cyclen component comprises a plurality of cyclen compounds.

10. A composition comprising an oil component and a component comprising at least one cyclen compound of a formula

wherein each of R 1 , nR 2 , R 3 and R 4 (R 1 -R 4 ) is a moiety independently selected from about C 5 -about C 24 linear and branched alkyl moieties; and n is an integer selected from 0- about 10.

11. The composition of claim 10 wherein each of R 1 -R 4 is a C 10 -C 20 alkyl moiety.

12. The composition of claim 11 wherein at least R 1 is a C 11 alkyl moiety.

13. The composition of claim 12 wherein each of R 1 -R 4 is independently a linear C 11 -C 18 alkyl moiety.

14. The composition of claim 13 wherein each of R 1 -R 4 is a linear, unsubstituted C 11 alkyl moiety.

15. The composition of claim 14 wherein n is 1-3.

16. The composition of claim 10 wherein said oil component is selected from base oils and formulated commercially-available motor oils.

17. The composition of claim 16 wherein said cyclen component is about 0.1 wt. % to about 1.0 wt. % of said composition.

18. The composition of claim 10 wherein said cyclen component comprises a plurality of cyclen compounds.

19. A composite comprising a metal substrate and an oil-cyclen composition of claim 1 coupled thereto.

20. The composite of claim 19 wherein said N-heteroatoms of said cyclen component of said composition are adsorbed to the surface of said substrate.

21. The composite of claim 20 wherein n is 1-3.

22. The composite of claim 21 wherein said adsorption is at temperatures up to and greater than about 200° C.

23. The composite of claim 19 wherein said oil component of said composition is a formulated commercially-available motor oil.

24. The composite of claim 19 wherein each of said cyclen R 1 -R 4 is independently a linear C 11 -C 18 alkyl moiety.

25. The composite of claim 24 wherein each of R 1 -R 4 is a linear unsubstituted C 11 alkyl moiety.

26. The composite of claim 19 providing a water contact angle greater than about 90 degrees.

27. A method of using a cyclen compound to reduce boundary lubrication friction, said method comprising:
providing opposed, first and second metal substrates;
applying an oil-cyclen composition of claim 1 to at least one said metal substrate; and
contacting said first and second metal substrates, said contact inducing boundary lubrication friction therebetween,

said composition in an amount sufficient to reduce boundary lubrication friction between said substrates, said reduction compared to boundary lubrication friction induced by substrate contact with application of a composition absent a said cyclen compound.

28. The method of claim 27 wherein said oil component is selected from base oils and formulated commercially-available motor oils.

29. The method of claim 27 wherein said cyclen component is about 0.1 wt. % to about 1.0 wt. % of said composition.

30. The method of claim 27 wherein each of said cyclen R 1 -R 4 is independently selected from linear C 11 -C 18 alkyl moieties.

31. The method of claim 30 wherein each of R 1 -R 4 is a linear unsubstituted C 11 alkyl moiety.

32. The method of claim 27 wherein said first and second metal substrates are selected from crank train, valve train and piston liner components of a gasoline engine.

33. The method of claim 29 wherein each of said cyclen R 1 -R 4 is a linear unsubstituted C 11 alkyl moiety.

34. The method of claim 33 wherein said contact is over a temperature range of about 20° C. to about 260° C.

35. The method of claim 34 wherein said friction reduction is over said temperature range.

Assignees

• Univ Northwestern

Inventors

• Marks Tobin J
• Wang Qian
• Chung Yip-Wah
• Delferro Massimiliano
• Desanker Michael
• He Xingliang

Classifications

• C10N2030/06

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

• C10M133/38 Primary

  Heterocyclic nitrogen compounds · CPC title

• C10N2030/56

  Boundary lubrication or thin film lubrication · CPC title

• C10N2030/08

  Resistance to extreme temperature · CPC title

• C10M2215/222

  Triazines · CPC title