Skip to main content
Log in

Supramolecular Gel Lubricants Based on Amino Acid Derivative Gelators

  • Original Paper
  • Published:
Tribology Letters Aims and scope Submit manuscript

Abstract

This work presents an amino acid-derived urea as the low molecular weight gelators (LMWGs) to solidify a variety of base-lubricating oils as well as different organic solvents. LMWGs self-assemble to form fibrous structures by intermolecular hydrogen bonding and van der Waals forces, and the gelation mechanism was proposed according to the NMR analysis. The obtained gels can liquefy upon heating and gelate again after cooling down, showing reversible temperature-induced phase transition. They showed good thixotropic characteristics so that they became mobile under shearing. Therefore, it a great advantage of these supramolecular gels to be used as potential high-performance semisolid lubricants, which can guarantee both good lubrication and the ability to restrain base oil creeping, oil permeation, or leakage, especially for the gears and rolling bearings. The tribological testing results suggest that these gel lubricants could effectively reduce friction and wear of sliding pairs compared with the corresponding blank base oils and greases.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

References

  1. Buerkle, L.E., Rowan, S.J.: Supramolecular gels formed from multi-component low molecular weight species. Chem. Soc. Rev. 41, 6089–6102 (2012)

    Article  Google Scholar 

  2. Pal, A., Ghosh, Y.K., Bhattacharya, S.: Molecular mechanism of physical gelation of hydrocarbons by fatty acid amides of natural amino acids. Tetrahedron 63, 7334–7348 (2007)

    Article  Google Scholar 

  3. Li, Y., Wang, X., Yu, T., Ma, Z., Yu, X., Xing, S.: A new photo-responsive organogel containing benzophenone group. Supramol. Chem. 26, 2–6 (2013)

    Article  Google Scholar 

  4. Reichwagen, J., Hopf, H., Guerzo, A.D., Belin, C., Bouas-Laurent, H., Desvergne, J.P.: Synthesis of 2,3-substituted tetracenes and evaluation of their self-assembling properties in organic solvents. Org. Lett. 7, 971–974 (2005)

    Article  Google Scholar 

  5. Yan, N., Xu, Z., Diehn, K., Raghavan, S., Fang, Y., Weiss, R.G.: Pyrenyl-linker-glucono gelators. Correlations of gel properties with gelator structures and characterization of solvent effects. Langmuir 29, 793–805 (2013)

    Article  Google Scholar 

  6. Abdallah, D.J., Weiss, R.G.: n-Alkanes gel n-Alkanes (and many other organic liquids). Langmuir 16, 352–355 (2000)

    Article  Google Scholar 

  7. Cao, X., Zhao, X., Gao, A., Xu, R.: Organogel formation based on bis-urea derivative. Supramol. Chem. 26, 1–6 (2014)

    Article  Google Scholar 

  8. Oda, R., Huc, I., Candau, S.J.: Gemini surfactants as new low molecular weight gelators of organic solvents and water. Angew. Chem. Int. Ed. 37, 2689–2691 (1998)

    Article  Google Scholar 

  9. Ishioka, Y., Minakuchi, N., Mizuhata, M., Maruyama, T.: Supramolecular gelators based on benzenetricarboxamides for ionic liquids. Soft Matter 10, 965–971 (2014)

    Article  Google Scholar 

  10. MakarevicÂ, J., Jokić, M., Perić, B., TomiŠić, V., Kojić –Prodić, B., Žinić, M.: Bis(amino acid) oxalyl amides as ambidextrous gelators of water and organic solvents supramolecular gels with temperature dependent assembly dissolution equilibrium. Chem. Eur. J. 7, 3328–3341 (2001)

    Article  Google Scholar 

  11. Bhuniya, S., Park, S.M., Kim, B.H.: Biotin–amino acid conjugates: An approach toward self-assembled hydrogelation. Org. Lett. 7, 1741–1744 (2005)

    Article  Google Scholar 

  12. Pal, A., Patra, T., Dey, J.: Physical gelation of organic liquids by achiral amino acid based amphiphilic gelators: effect of chirality. Chin. Chem. Lett. 556, 245–250 (2013)

    Google Scholar 

  13. Li, Y., Liu, K., Liu, J., Peng, J., Feng, X., Fang, Y.: Amino acid derivatives of cholesterol as “latent” organogelators with hydrogen chloride as a protonation reagent. Langmuir 22, 7016–7020 (2006)

    Article  Google Scholar 

  14. Samai, S., Dey, J., Biradha, K.: Amino acid based low-molecular-weight tis(bis-amido) organogelators. Soft Matter 7, 2121–2126 (2011)

    Article  Google Scholar 

  15. Saha, S., Bachl, J., Kundu, T., Diaz, D.D., Banerjee, R.: Amino acid-based multiresponsive low-molecular weight metallohydrogels with load-bearing and rapid self-healing abilities. Chem. Commun. 50, 3004–3006 (2014)

    Article  Google Scholar 

  16. Basak, S., Nanda, J., Banerjee, A.: Multi-stimuli responsive self-healing metallo-hydrogels: tuning of the gel recovery property. Chem. Commun. 50, 2356–2359 (2014)

    Article  Google Scholar 

  17. Matta, C., Joly-Pottuz, L., De Barros Bouchet, M., Martin, J., Kano, M., Zhang, Q., Goddard, W.: Superlubricity and tribochemistry of polyhydric alcohols. Phys. Rev. B. 78, 085436 (2008)

    Article  Google Scholar 

  18. Cai, M., Guo, R., Zhou, F., Liu, W.: Lubricating a bright future: lubrication contribution to energy saving and low carbon emission. Sci. China: Technol. Sci. 56, 2888–2913 (2013)

    Article  Google Scholar 

  19. Nobuyoshi, O., Sobahan, M., Kazuo, M., Kentaro, S., Yuji, Y., Yoshitaka, T., Shigeki, M., Yuji, S.: Tribological properties and film formation behavior of thermoreversible gel lubricants. Tribol. Trans. 53, 722–730 (2010)

    Article  Google Scholar 

  20. Takahashi, K., Shitara, Y., Kaimai, T., Kanno, A., Mori, S.: Lubricating properties of TR gel-lube—Influence of chemical structure and content of gel agent. Tribol. Int. 43, 1577–1583 (2010)

    Article  Google Scholar 

  21. Cai, M., Liang, Y., Zhou, F., Liu, W.: Functional ionic gels formed by supramolecular assembly of a novel low molecular weight anticorrosive/antioxidative gelator. J. Mater. Chem. 21, 13399–13405 (2011)

    Article  Google Scholar 

  22. Yu, Q., Fan, M., Li, D., Song, Z., Cai, M., Zhou, F., Liu, W.: Thermoreversible gel lubricants through universal supramolecular assembly of a nonionic surfactant in a variety of base lubricating liquids. ACS Appl. Mater. Interfaces 6, 15738–15794 (2014)

    Google Scholar 

  23. Minakuchi, N.H., Yamaki, K., Tenno, D., Nakashima, S., Goto, K., Mizuhata, M., Maruyama, T.: Versatile supramolecular gelators that can harden water, organic solvents and ionic liquids. Langmuir 28, 9259–9266 (2012)

    Article  Google Scholar 

  24. Wei, J., Cai, M., Zhou, F., Liu, W.: Candle soot as particular lubricant additives. Tribol. Lett. 53, 521–531 (2014)

    Article  Google Scholar 

  25. Li, D., Gao, P., Sun, X., Zhang, S., Zhou, F., Liu, W.: The study of TEMPOs As additives in different lubrication oils for steel/steel contacts. Tribol. Int. 73, 83–87 (2014)

    Article  Google Scholar 

  26. Pal, A., Voudouris, P., Koenigs, M.M.E., Besenius, P., Wyss, H.M., Degirmenci, V., Sijbesma, R.P.: Topochemical polymerization in self-assembled rodlike micelles of bisurea bolaamphiphiles. Soft Matter 10, 952–956 (2014)

    Article  Google Scholar 

  27. Loos, M.D., Ligtenbarg, A.G.J., Esch, J.V., Kooijman, H., Spek, A.L., Hage, R., Kellogg, R.M., Feringa, B.L.: Tripodal tris-urea derivatives as gelators for organic solvents. Eur. J. Org. Chem. 2000, 3675–3678 (2000)

    Article  Google Scholar 

  28. Goh, C.Y., Mocerino, M., Ogden, M.I.: Macrocycl. Gel. Supramol. Chem. 25, 555–566 (2013)

    Article  Google Scholar 

  29. Skilling, K.J., Citossi, F., Bradshaw, T.D., Ashford, M., Kellam, B., Marlow, M.: Insights into low molecular mass organic gelators: a focus on drug delivery and tissue engineering applications. Soft Matter 10, 237–256 (2014)

    Article  Google Scholar 

  30. Babu, S., Praveen, V., Ajayaghosh, A.: Functional π-gelators and their applications. Chem. Rev. 114, 1933–2129 (2014)

    Article  Google Scholar 

  31. Basit, H., Pal, A., Sen, S., Bhattacharya, S.: Two-component hydrogels comprising fatty acids and amines: structure, properties, and application as a template for the synthesis of metal nanoparticles. Chem. Eur. J. 14, 6534–6545 (2008)

    Article  Google Scholar 

  32. Wang, D., Hao, J.: Multiple-stimulus-responsive hydrogels of cationic surfactants and azoic salt mixtures. Colloid Polym. Sci. 291, 2935–2946 (2013)

    Article  Google Scholar 

  33. Suzuki, M., Nakajima, Y., Yumoto, M., Kimura, M., Shirai, H., Hanabusa, K.: Effects of hydrogen bonding and van der waals interactions on organogelation using designed low-molecular-weight gelators and gel formation at room temperature. Langmuir 19, 8622–8624 (2003)

    Article  Google Scholar 

  34. Wang, C., Zhang, D., Zhu, D.: A chiral low-molecular-weight gelator based on binaphthalene with two urea moieties modulation of the CD spectrum after gel formation. Langmuir 23, 1478–1482 (2007)

    Article  Google Scholar 

  35. Duncan, D.C., Whitten, D.G.: 1H NMR Investigation of the composition, structure, and dynamics of cholesterol–stilbene tethered dyad organogels. Langmuir 16, 6445–6452 (2000)

    Article  Google Scholar 

  36. Allix, F., Curcio, P., Pham, Q.N., Pickaert, G., Jamart-Gregoire, B.: Evidence of intercolumnar ππ stacking interactions in amino-acid-based low-molecular-weight organogels. Langmuir 26, 16818–16827 (2010)

    Article  Google Scholar 

  37. Nandi, S., Altenbach, H.J., Jakob, B., Lange, K., Ihizane, R., Schneider, M.P., Gün, Ü., Mayer, A.: Amphiphiles based on d-glucose efficient low molecular weight gelators. Org. Lett. 14, 3826–3829 (2012)

    Article  Google Scholar 

  38. Mandal, D., Kar, T., Das, P.K.: Pyrene-based fluorescent ambidextrous gelators: scaffolds for mechanically robust SWNT-gel nanocomposites. Chem. Eur. J. 20, 1349–1358 (2014)

    Article  Google Scholar 

  39. Rodriguez-Llansola, F., Hermida-Merino, D., Nieto-Ortega, B., Ramirez, F.J., Navarrete, J.T., Casado, J., Hamley, I.W., Escuder, B., Hayes, W., Miravet, J.F.: Assembly studies of a chiral bisurea-based superhydrogelator. Chem. Eur. J. 18, 14725–14731 (2012)

    Article  Google Scholar 

  40. Cai, M., Liang, Y., Yao, M., Xia, Y., Zhou, F., Liu, W.: Imidazolium ionic liquids as antiwear and antioxidant additive in poly(ethylene glycol) for steel/steel contacts. ACS Appl. Mater. Interfaces 2, 870–876 (2010)

    Article  Google Scholar 

  41. Daisuke, T., Sobahan, M., Shigeki, M., Nobuyoshi, O., Yuji, S.: EHL oil film behavior of thermo-reversible gel-lubricants. Tribol. Online 3, 90–93 (2008)

    Article  Google Scholar 

  42. Yuji, S., Aoi, K., Takashi, K., Shigeyuki, M.: Effect of amide molecular structure on tribological properties of thermoreversible gel lubricant. Tribol. Online 5, 284–290 (2010)

    Article  Google Scholar 

  43. National Institute of Standards and Technology. NIST X-ray Photoelectron Spectroscopy Database, version 4.1, 2012. http://srdata.nist.gov/xps/

  44. Cai, M., Zhao, Z., Liang, Y., Zhou, F., Liu, W.: Alkyl imidazolium ionic liquids as friction reduction and anti-wear additive in polyurea grease for steel/steel contacts. Tribol. Lett. 40, 215–224 (2010)

    Article  Google Scholar 

  45. Cai, M., Liang, Y., Zhou, F., Liu, W.: A novel imidazolium salt with antioxidation and anticorrosion dual functionalities as the additive in poly(ethylene glycol) for steel/steel contacts. Wear 306, 197–208 (2013)

    Article  Google Scholar 

  46. Song, Z., Fan, M., Liang, Y., Zhou, F., Liu, W.: Lithium-based ionic liquids: in situ-formed lubricant additive only by blending. Tribol. Lett. 49, 127–133 (2012)

    Article  Google Scholar 

Download references

Acknowledgments

The authors acknowledge the financial support from the NSFC (51305428, 21173243), ‘‘973’’ program (2013CB632301) and West Light Foundation of the Chinese Academy of Sciences.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Meirong Cai or Feng Zhou.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 6058 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yu, Q., Li, D., Cai, M. et al. Supramolecular Gel Lubricants Based on Amino Acid Derivative Gelators. Tribol Lett 61, 16 (2016). https://doi.org/10.1007/s11249-015-0634-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s11249-015-0634-y

Keywords

Navigation