Lubricating oil friction modifier and preparation method therefor and application thereof

Patent metadata

Field	Value
Publication number	US-12264292-B2
Application number	US-202218577522-A
Country	US
Kind code	B2
Filing date	Jan 26, 2022
Priority date	Jul 6, 2021
Publication date	Apr 1, 2025
Grant date	Apr 1, 2025

Abstract

A lubricating oil friction modifier and a preparation method therefor and use thereof are provided. The lubricating oil friction modifier has a chemical formula of A x B y+ (C − ) y . In the formula, A is a perfluoropolyether acyl group, B y+ represents a cationic group having x amino groups and y ammonium ions, C − is BF 4 − , PF 6 − , AsF 6 − , FAP − , TFSI − , Mn 2 O 4 or ClO 4 − , x is an integer greater than or equal to 1, y is an integer greater than or equal to 1, and x+y≥2. The lubricating oil friction modifier has a good solubility with fluorine oil and fluorine grease, will not precipitate in the fluorine oil and the fluorine grease after being added, and can significantly improve the wear resistance of a lubricating oil such as the fluorine oil and the fluorine grease.

First claim

The invention claimed is:

1. A lubricating oil friction modifier, having a chemical formula of A x B y+ (C − ) y , wherein,
A represents a perfluoropolyether acyl group,
B y+ represents a cationic group having x amino groups and y ammonium ions,
C − is BF 4 − (boron tetrafluoride anion), PF 6 − (hexafluorophosphate anion), AsF 6 − (hexafluoroarsenate anion), FAP − (trifluorotri(pentafluoroethyl)phosphate anion), TFSI − (bistrifluoromethylsulfonimide anion), Mn 2 O 4 − (manganate), or ClO 4 − (perchlorate),
x is an integer greater than or equal to 1, y is an integer greater than or equal to 1, and x+y≥2.

2. The lubricating oil friction modifier according to claim 1 , wherein, A is a group of formula K, Y, Z, or D:

wherein m and n each are independently positive integers, m is 1-99, and n is 1-10.

3. The lubricating oil friction modifier according to claim 1 , wherein B is a polyamine compound or a dendrimer;
wherein the polyamine compound is selected from ethylenediamine, triethyldiamine, p-biphenyldiamine, 1,4-phenylenediamine, 1,4-phenylenedimethanamine and tri(2-aminoethyl)amine;
the dendrimer is a PAMAM dendrimer having a core selected from ethylenediamine, triethyldiamine, p-biphenyldiamine, 1,4-phenylenediamine, 1,4-phenylenedimethanamine, and tri(2-aminoethyl)amine, and has a generation number of 0 to 10.

4. The lubricating oil friction modifier according to claim 3 , wherein, in A x B y+ (C − ) y , x+y≥3.

5. A preparation method for the lubricating oil friction modifier of claim 1 , comprising:
S100, performing acylation reaction between a perfluoropolyether acylating agent and a polyamine compound or a dendrimer with an amino end group in the presence of a solvent and a promoter to obtain a solution of a first reaction product;
S200, adding an acid and a salt of at least one anion selected from BF 4 − , PF 6 − , trifluorotri(pentafluoroethyl)phosphate anion, bistrifluoromethylsulfonimide anion, Mn 2 O 4 − , and ClO 4 − to the solution of the first reaction product obtained in step S100 to obtain a solution of a second reaction product; and
S300, neutralizing the solution of the second reaction product obtained in step S200, performing liquid separation, and removing the solvent therefrom to obtain a target product.

6. The preparation method according to claim 5 , wherein, the perfluoropolyether acylating agent in step S100 is at least one acylating agent selected from acylating agents of formulae K′, Y′, Z′ and D′,

wherein, R 1 , R 2 , R 3 and R 4 each are independently fluorine, chlorine, bromine, anhydride, or hydroxyl group; and/or
the polyamine compound in step S100 is selected from ethylenediamine, triethyldiamine, p-biphenyldiamine, 1,4-phenylenediamine, 1,4-phenylenedimethanamine and tri(2-aminoethyl)amine; and/or the dendrimer is a PAMAM dendrimer having the core selected from ethylenediamine, triethyldiamine, p-biphenyldiamine, 1,4-phenylenediamine, 1,4-phenylenedimethanamine, and tri(2-aminoethyl)amine, and has a generation number of 0 to 10; and/or
the promoter in step S100 is pyridine, triethylamine, or a mixture thereof; and/or
the solvent in step S100 is 1,1,2-trifluorotrichloroethane; and/or
the step S100 further comprises:
S101, mixing the perfluoropolyether acylating agent with the solvent and the promoter to obtain a mixture;
S102, adding the polyamine compound or the dendrimer with the amino group as the terminal group to the mixture obtained in step S101 at a temperature of −5 to 0° C.; and refluxing to obtain a refluxing reaction product; and
S103, neutralizing the refluxing reaction product obtained in step S102, and performing liquid separation to obtain the solution of the first reaction product.

7. The preparation method according to claim 5 , wherein the salt in step S200 is at least one selected from lithium salt, sodium salt, and potassium salt; and/or
the acid in step S200 is at least one selected from nitric acid, sulfuric acid, and hydrochloric acid; and/or
in each of steps S103 and S300, an aqueous solution containing at least one of sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, sodium hydroxide and potassium hydroxide is independently used for neutralization.

8. A lubricating oil composition, comprising 90-99 weight parts of a base lubricating oil and 1-10 weight parts of the lubricating oil friction modifier of claim 1 , wherein the base lubricating oil is at least one selected from fluorine oil and fluorine grease.

9. The lubricating oil composition according to claim 8 , wherein the lubricating oil composition comprises 92-97 weight parts of the base lubricating oil and 3-8 weight parts of the lubricating oil friction improver.

10. The lubricating oil friction modifier according to claim 2 , wherein A is a group of formula Z or D, and a value of m/n is 0.2-25.

11. The lubricating oil friction modifier according to claim 10 , wherein the value of m/n is 0.2-15.

12. The lubricating oil friction modifier according to claim 10 , wherein the value of m/n is 0.2-10.

13. The lubricating oil friction modifier according to claim 3 , wherein the dendrimer has a generation number 0 to 4.

14. The lubricating oil friction modifier according to claim 3 , wherein the dendrimer has a generation number 0 to 3.

15. The lubricating oil friction modifier according to claim 4 , wherein, in A x B y+ (C − ) y , x+y≥4.

16. The lubricating oil friction modifier according to claim 4 , wherein B is a dendrimer, and in A x B y+ (C − ) y , x+y=2 2+d , d is a number of generation of the dendrimer, and wherein d is 0 or 1, x is in a range of 2-6, and y is in a range of 2-6.

17. The preparation method according to claim 6 , wherein the dendrimer has a generation number 0 to 4.

18. The preparation method according to claim 6 , wherein, the dendrimer has a generation number of 0 to 3.

Assignees

• China Petroleum & Chem Corp

Inventors

• E Hongjun
• Du Xueling
• Xin Hu
• Lei Ling
• Li Cheng
• Jiang Dandan
• Jin Jiajia
• Baheti Ahebota

Classifications

• C10M149/00

  Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen · CPC title

• C10M2217/046

  Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers · CPC title

• C10M2213/06

  Perfluoro polymers · CPC title

• C10N2020/075

  Dendrimers · CPC title

• C10N2020/077

  Ionic Liquids · CPC title