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Research Papers: Lubricants

A Three-Dimensional Quantitative Structure Tribo-Ability Relationship Model

[+] Author and Article Information
Xinlei Gao, Zhan Wang, Hong Zhang

School of Chemical and
Environmental Engineering,
Wuhan Polytechnic University,
Wuhan, Hubei 430023, China

Kang Dai

College of Pharmacy,
South-Central University for Nationalities,
Wuhan, Hubei 430074, China
e-mail: kangdai1688@163.com

1Corresponding author.

Contributed by the Tribology Division of ASME for publication in the JOURNAL OF TRIBOLOGY. Manuscript received May 28, 2014; final manuscript received December 6, 2014; published online February 5, 2015. Assoc. Editor: Min Zou.

J. Tribol 137(2), 021802 (Apr 01, 2015) (8 pages) Paper No: TRIB-14-1119; doi: 10.1115/1.4029388 History: Received May 28, 2014; Revised December 06, 2014; Online February 05, 2015

The prediction of lubrication characteristics for compounds through tribological models would aid in the discovery of new lubricant additives and improved lubricant design. But until recently, the field of tribological prediction has been sparse and not systematic. Tribological processes are complex and involve molecular energy exchange as well as conformation transitions. We have developed a platform of a “quantitative structure tribo-ability relationship (QSTR),” which enables us to introduce well-developed quantitative structure–activity relationships (QSAR) methods into tribology systematically. The present study applies “evaluation of infrared vibration-based” (EVA) descriptors, which are three-dimensional (3D) QSAR descriptors to simulate infrared (IR) vibration properties of molecules, in order to establish the QSTR prediction model. As structural changes take place under friction loads, the EVA descriptors characterize both molecular energy and conformations. The results show a strong correlation and robust predictability of the EVA model to tribological parameters. The approach paves a way to a systematic QSTR.

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References

Hansch, C., and Steward, A. R., 1964, “The Use of Substituent Constants in the Analysis of the Structure–Activity Relationship in Penicillin Derivatives,” J. Med. Chem., 7(6), pp. 691–694. [CrossRef] [PubMed]
Prasanna, S., and Doerksen, R. J., 2009, “Topological Polar Surface Area: A Useful Descriptor in 2D-QSAR,” Curr. Med. Chem., 16(1), pp. 21–41. [CrossRef] [PubMed]
Cramer, R. D., III, Patterson, D. E., and Bunce, J. D., 1988, “Comparative Molecular Field Analysis (CoMFA). 1. Effect of Shape on Binding of Steroids to Carrier Proteins,” J. Am. Chem. Soc., 110(18), pp. 5959–5967. [CrossRef] [PubMed]
Liu, X., Zhou, F., Liang, Y., and Liu, W., 2006, “Tribological Performance of Phosphonium Based Ionic Liquids for an Aluminum-on-Steel System and Opinions on Lubrication Mechanism,” Wear, 261(10), pp. 1174–1179. [CrossRef]
Yu, G., Zhou, F., Liu, W., Liang, Y., and Yan, S., 2006, “Preparation of Functional Ionic Liquids and Tribological Investigation of Their Ultra-Thin Films,” Wear, 260(9–10), pp. 1076–1080. [CrossRef]
Jiménez, A. E., Bermúdez, M. D., Iglesias, P., Carrión, F. J., and Martínez-Nicolás, G., 2006, “1-N-Alkyl-3-Methylimidazolium Ionic Liquids as Neat Lubricants and Lubricant Additives in Steel–Aluminium Contacts,” Wear, 260(7–8), pp. 766–782. [CrossRef]
Singh, H., and Gulati, I. B., 1990, “Tribological Behaviour of Some Hydrocarbon Compounds and Their Blends,” Wear, 139(2), pp. 425–437. [CrossRef]
Martin, J. M., Grossiord, C., Varlot, K., Vacher, B., and Igarashi, J., 2000, “Synergistic Effects in Binary Systems of Lubricant Additives: A Chemical Hardness Approach,” Tribol. Lett., 8(4) pp. 193–201. [CrossRef]
Edgar, J., and Hurley, S., 2004, “The Use of Quantitative Structure Activity Relationships (QSAR) in Traction Fluid Design,” SAE Technical Paper No. 2004-01-2009. [CrossRef]
Barr, D., and Friend, C., 2005, “The Development of Predictive Models for Non-Acidic Lubricity Agents (NALA) Using Quantitative Structure Activity Relationships (QSAR),” SAE Technical Paper No. 2005-01-3900. [CrossRef]
Ferguson, A. M., Heritage, T., Jonathon, P., Pack, S. E., Phillips, L., Rogan, J., and Snaith, P. J., 1997, “EVA: A New Theoretically Based Molecular Descriptor for Use in QSAR/QSPR Analysis,” J. Comput. Aided Mol. Des., 11(2), pp. 143–152. [CrossRef] [PubMed]
Ginn, C. M. R., Turner, D. B., Willett, P., Ferguson, A. M., and Heritage, T. W., 1997, “Similarity Searching in Files of Three-Dimensional Chemical Structures: Evaluation of the EVA Descriptor and Combination of Rankings Using Data Fusion,” J. Chem. Inf. Comput. Sci., 37(1), pp. 23–37. [CrossRef]
Clark, R. D., 1996, “Synthesis and QSAR of Herbicidal 3-Pyrazolyl α,α,α-Trifluorotolyl Ethers,” J. Agric. Food Chem., 44(11), pp. 3643–3652. [CrossRef]
Turner, D. B., Willett, P., Ferguson, A. M., and Heritage, T., 1997, “Evaluation of a Novel Infra-Red Range Vibration-Based Descriptor (EVA) for QSAR Studies: 1. General Application,” J. Comput. Aided Mol. Des., 11(4), pp. 409–422. [CrossRef] [PubMed]
Heritage, T. W., Ferguson, A. M., Turner, D. B., and Willett, P., 1998, “EVA: A Novel Theoretical Descriptor for QSAR Studies,” Perspect. Drug Discovery Des., 9–11, pp. 381–398. [CrossRef]
Nilsson, B. M., Sundquist, S., Johansson, G., Nordvall, G., Glas, G., Nilvebrant, L., and Hacksell, U., 1995, “3-Heteroaryl-Substituted Quinuclidin-3-ol and Quinuclidin-2-ene Derivatives as Muscarinic Antagonists. Synthesis and Structure–Activity Relationships,” J. Med. Chem., 38(3), pp. 473–487. [CrossRef] [PubMed]
Zhang, J., 1999, “The Relationship Between Additives Molecular Structure and Their Tribological Properties and the Mechanism of Boundary Lubrication,” Ph.D. thesis, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, China.
Zhang, J., Liu, W., Xue, Q., and Wang, Q., 1998, “Investigation of the Friction and Wear Behaviors of Cu(I) and Cu(II) Dioctyldithiophosphates as Additives in Liquid Paraffin,” Wear, 216(1), pp. 35–40. [CrossRef]
Zhang, J., Zhang, Z., Liu, W., and Xue, Q., 1998, “The Tribological Behaviors of 2-Mercaptobenzoxazole Derivatives as Additives in Liquid Paraffin,” Wear, 219(2), pp. 184–187. [CrossRef]
Zhang, J., Liu, W., and Xue, Q., 1998, “Tribological Study of a Mannich Compound of 2-Mercaptobenzimidazole in Liquid Paraffin,” Tribol. Int., 31(12), pp. 767–770. [CrossRef]
Zhang, J., Liu, W., and Xue, Q., 1999, “The Friction and Wear Behaviors of S-[2-S-(2-Hydroxylpropy1)Benthiazole] Dioctyldithiocarbamic Acid Ester as Additive in Liquid Paraffin,” Wear, 224(1), pp. 50–55. [CrossRef]
Zhang, J., Xue, Q., and Liu, W., 1999, “The Tribological Properties of the Heterocyclic Compound Containing S, N, O, and B as Additive in Liquid Paraffin,” Wear, 224(1), pp. 68–72. [CrossRef]
Zhang, J., Liu, W., Xue, Q., and Ren, T., 1999, “Study of N and S Heterocyclic Compound as a Potential Lubricating Oil Additive,” Wear, 224(1), pp. 160–164. [CrossRef]
Zhang, J., Liu, W., and Xue, Q., 1999, “The Effect of Molecular Structure of Heterocyclic Compounds Containing N, O and S on Their Tribological Performance,” Wear, 231(1), pp. 65–70. [CrossRef]
Zhang, J., Liu, W., and Xue, Q., 1999, “A Study of 2-(Dibutylaminomethyl)-Thiobenzimidazole as an Oil Additive,” Wear, 231(2), pp. 279–284. [CrossRef]
Zhang, J., Yang, L., Liu, W., and Xue, Q., 1999, “The Effect of Poly[Hexane Dioic Acid-1,2-Propylene-Glycol] Ester on the Wear of Steel,” Wear, 232(1), pp. 61–66. [CrossRef]
Zhang, J., Xue, Q., and Liu, W., 1999, “Tribological Properties of the Film Formed by 2-(n-Dodecyldithio)-Benzothiazole as Additive in Liquid Paraffin,” Wear, 236(1), pp. 34–38. [CrossRef]
Xue, Q., Zhang, J., Liu, W., and Yang, S., 1999, “The Friction and Wear Behavior of 2-(n-Alkyldithio)-Benzimidazole as Additives in Liquid Paraffin,” Tribol. Lett., 7(1), pp. 27–30. [CrossRef]
Zhang, J., Yang, S., Liu, W., and Xue, Q., 2000, “A Study of S-[2-(2-Hydroxy Genacetyl)Thiobenzothiazol-1-yl]Dialkyldithiophosphates as Novel Additives in Liquid Paraffin,” Wear, 237(1), pp. 49–53. [CrossRef]
Zhang, J., Yang, S., and Xue, Q., 2000, “Preparation and Characterization of Ni(OH)2 Nanoparticles Coated With Dialkyldithiophosphate,” J. Mater. Res., 15(2), pp. 541–545. [CrossRef]
Zhang, J., Yang, S., Liu, W., and Xue, Q., 1999, “A Study of 2-(n-Alkyldithio)-Benzoxazoles as Novel Additives,” Tribol. Lett., 7(4), pp. 173–177. [CrossRef]
sybyl-x 1.1, 2009, Tripos International, St. Louis, MO.
Stewart, J. J. P., 2009, “MOPAC2009, Stewart Computational Chemistry,” Colorado Springs, CO, http://OpenMOPAC.net
Dai, K., and Gao, X., 2013, “Estimating Antiwear Properties of Lubricant Additives Using a Quantitative Structure Tribo-Ability Relationship Model With Back Propagation Neural Network,” Wear, 306(1–2), pp. 242–247. [CrossRef]
Boulesteix, A. L., and Strimmer, K., 2007, “Partial Least Squares: A Versatile Tool for the Analysis of High-Dimensional Genomic Data,” Briefings Bioinf., 8(1), pp. 32–44. [CrossRef]
Jahanmir, S., 1985, “Chain Length Effects in Boundary Lubrication,” Wear, 102(4) pp. 331–333. [CrossRef]

Figures

Grahic Jump Location
Fig. 1

Comparison of EVA spectra and observed IR spectra

Grahic Jump Location
Fig. 2

Prediction performance of EVA model. (a) Prediction of VS. (b) Prediction of FF. (OBS: the observed or experimental scale of antiwear and antifriction; PRED: the predicted scale of antiwear and antifriction in the models).

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Fig. 3

The PLS coefficients of antiwear and antifriction models. (a) The curve of antiwear model and (b) the curve of antifriction model. Horizontal axis denotes frequency ν; longitudinal axis denotes the value of PLS coefficient (defined in Eq. (5)).

Grahic Jump Location
Fig. 4

The increment of EVA–PLS model when butyl is substituted with octyl (DEVA: compound 8 versus compound 9). (a) The VS as a function of the vector DEVA (the EVA descriptors difference of compound pair). (b) The FF as a function of the vector DEVA (the EVA descriptors difference of compound pair).

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Fig. 5

The increment of EVA–PLS model when butyl is substituted with decyl (DEVA: compound 33 versus compound 35). (a) The VS as a function of the vector DEVA (the EVA descriptors difference of compound pair). (b) The FF as a function of the vector DEVA (the EVA descriptors difference of compound pair).

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Fig. 6

The increment of EVA–PLS model when butyl is substituted with dodecyl (DEVA: compound 7 versus compound 9). (a) The VS as a function of the vector DEVA (the EVA descriptors difference of compound pair). (b) The FF as a function of the vector DEVA (the EVA descriptors difference of compound pair).

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Fig. 7

The increment of EVA–PLS model when phenyl thiazole is substituted with benzoxazole (DEVA: compound 29 versus compound 31). (a) The VS as a function of the vector DEVA (the EVA descriptors difference of compound pair). (b) The FF as a function of the vector DEVA (the EVA descriptors difference of compound pair).

Grahic Jump Location
Fig. 8

The increment of EVA–PLS model when phenyl thiazole is substituted with benzimidazole (DEVA: compound 27 versus compound 28). (a) The VS as a function of the vector DEVA (the EVA descriptors difference of compound pair). (b) The FF as a function of the vector DEVA (the EVA descriptors difference of compound pair).

Grahic Jump Location
Fig. 9

The increment of EVA–PLS model when propyl is substituted with allyl (DEVA: compound 31 versus compound 28). (a) The VS as a function of the vector DEVA (the EVA descriptors difference of compound pair). (b) The FF as a function of the vector DEVA (the EVA descriptors difference of compound pair).

Grahic Jump Location
Fig. 10

The increment of EVA–PLS model with xanthionyl (DEVA: compound 13 versus compound 32). (a) The VS as a function of the vector DEVA (the EVA descriptors difference of compound pair). (b) The FF as a function of the vector DEVA (the EVA descriptors difference of compound pair).

Grahic Jump Location
Fig. 11

The increment of EVA–PLS model with thiophosphoryl (DEVA: compound 17 versus compound 21). (a) The VS as a function of the vector DEVA (the EVA descriptors difference of compound pair). (b) The FF as a function of the vector DEVA (the EVA descriptors difference of compound pair).

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