Lubricating oil friction modifier and preparation method therefor and application thereof

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.sub.xB.sup.y+(C.sup.).sub.y. In the formula, A is a perfluoropolyether acyl group, B.sup.y+ represents a cationic group having x amino groups and y ammonium ions, C.sup. is BF.sub.4.sup., PF.sub.6.sup., AsF.sub.6.sup., FAP.sup., TFSI.sup., Mn.sub.2O.sub.4 or ClO.sub.4.sup., x is an integer greater than or equal to 1, y is an integer greater than or equal to 1, and x+y2. 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.

Claims

1. A lubricating oil friction modifier, having a chemical formula of A.sub.xB.sup.y+(C.sup.).sub.y, wherein, A represents a perfluoropolyether acyl group, B.sup.y+ represents a cationic group having x amino groups and y ammonium ions, C.sup. is BF.sub.4.sup. (boron tetrafluoride anion), PF.sub.6.sup. (hexafluorophosphate anion), AsF.sub.6.sup. (hexafluoroarsenate anion), FAP.sup. (trifluorotri(pentafluoroethyl)phosphate anion), TFSI.sup. (bistrifluoromethylsulfonimide anion), Mn.sub.2O.sub.4.sup. (manganate), or ClO.sub.4.sup. (perchlorate), x is an integer greater than or equal to 1, y is an integer greater than or equal to 1, and x+y2.

2. The lubricating oil friction modifier according to claim 1, wherein, A is a group of formula K, Y, Z, or D: ##STR00005## 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.sub.xB.sup.y+(C.sup.).sub.y, x+y3.

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.sub.4.sup., PF.sub.6.sup., trifluorotri(pentafluoroethyl)phosphate anion, bistrifluoromethylsulfonimide anion, Mn.sub.2O.sub.4.sup., and ClO.sub.4.sup. 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, ##STR00006## wherein, R.sub.1, R.sub.2, R.sub.3 and R.sub.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.sub.xB.sup.y+(C.sup.).sub.y, x+y4.

16. The lubricating oil friction modifier according to claim 4, wherein B is a dendrimer, and in A.sub.xB.sup.y+(C.sup.).sub.y, x+y=2.sup.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.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

(1) The FIGURE is a preparation scheme for a lubricating oil friction modifier according to an embodiment the present invention.

DETAILED DESCRIPTION OF THE EMBODIMENTS

(2) In the following, the present invention will be further illustrated in combination with specific examples, which will not constitute any limitation on the present invention.

Example 1

(3) Referring to the FIGURE, a lubricating oil friction modifier is prepared by the following method.

(4) (1) 3 g of K-type perfluoropolyether acyl fluoride (provided by Sinopec Lubricant Co., Ltd., n=7), 1 mL pyridine, and 100 mL of F113 (1,1,2-trifluorotrichloroethane) were added into a 300 mL three-necked flask under stirring. Under a condition of 3 C., 2 g of a 0th generation PAMAM dendrimer (purchased from Weihai Chenyuan Organosilicone New Materials Co., Ltd., trade name: CYD-100A, with ethylenediamine as a core) was added dropwise. After completion of dropwise addition, the resultant was stirred for 1 h at 5 to 0 C. Then the resultant was subjected to gradual temperature rise and reacted under refluxing for 3 h, the heating was stopped. When the reaction temperature was lowered to 25-30 C., 150 mL of saturated sodium bicarbonate aqueous solution was added, the resultant was stirred for 5 min, and a lower-layer solution was collected through a separating funnel.

(5) (2) 2 mL of nitric acid having a concentration of 98% was added into the above solution, the resultant was stirred at room temperature for 7 min, then 8 g of lithium bistrifluoromethylsulfonimide was added, the resultant was allowed to react under stirring for 5 h, and then the reaction was stopped. Then 150 mL of saturated sodium bicarbonate aqueous solution was added, the resultant was stirred at room temperature for 5 min, and a lower-layer solution was collected through a separating funnel. To this lower-layer solution, 150 mL of saturated sodium bicarbonate aqueous solution was further added, the resultant was stirred at room temperature for 5 min, and a lower-layer solution was collected through a separating funnel.

(6) (3) After the F113 solvent was removed from the above lower-layer solution through vacuum distillation, 4 g of viscous liquid was obtained, which was as a target product.

(7) The obtained product was characterized by infrared spectroscopy, wherein, 2929.69 cm.sup.1 and 1456.85-1305.25 cm.sup.1 are CH.sub.2 absorption peaks; 2375.19-2208.8 cm.sup.1 are amine salt absorption peaks; 1819.08 cm.sup.1 is a C(O) absorption peak; 1696.82 cm.sup.1 and 1635.98 cm.sup.1 are C(O)NH absorption peaks; and 1116.10 cm.sup.1 is a tertiary amine absorption peak.

Example 2

(8) (1) 3 g of K-type perfluoropolyether acyl fluoride (provided by Sinopec Lubricant Co., Ltd., n=10), 1 mL pyridine, and 100 mL of F113 (1,1,2-trifluorotrichloroethane) were added into a 300 mL three-necked flask under stirring. Under a condition of 3 C., 1.5 g of a second generation PAMAM dendrimer (purchased from Weihai Chenyuan Organosilicone New Materials Co., Ltd., trade name: CYD-120A, with ethylenediamine as a core) was added dropwise. After completion of dropwise addition, the resultant was stirred for 1 h at 5 to 0 C. Then the resultant was subjected to gradual temperature rise and reacted under refluxing for 3 h, the heating was stopped. When the reaction temperature was lowered to 25-30 C., 150 mL of saturated sodium bicarbonate aqueous solution was added, the resultant was stirred for 5 min, and a lower-layer solution was collected through a separating funnel.

(9) (2) 2 mL of nitric acid having a concentration of 98% was added into the above solution, the resultant was stirred at room temperature for 7 min, then 10 g of BF.sub.4Li was added, the resultant was allowed to react under stirring for 5 h, and then the reaction was stopped. Then 150 mL of saturated sodium bicarbonate aqueous solution was added, the resultant was stirred at room temperature for 5 min, and a lower-layer solution was collected through a separating funnel. To this lower-layer solution, 150 mL of saturated sodium bicarbonate aqueous solution was further added, the resultant was stirred at room temperature for 5 min, and a lower-layer solution was collected through a separating funnel.

(10) (3) After the F113 solvent was removed from the above lower-layer solution through vacuum distillation, 3.8 g of viscous liquid was obtained, which was as a target product.

(11) The obtained product was characterized by infrared spectroscopy, and the positions of individual peaks were substantially the same as those in Example 1.

Example 3

(12) (1) 3 g of Z-type perfluoropolyether acyl fluoride (provided by Sinopec Lubricant Co., Ltd., m=2, n=10), 1 mL pyridine, and 100 mL of F113 (1,1,2-trifluorotrichloroethane) were added into a 300 mL three-necked flask under stirring. Under a condition of 3 C., 1.8 g of a first generation PAMAM dendrimer (purchased from Weihai Chenyuan Organosilicone New Materials Co., Ltd., trade name: CYD-110A, with triethyldiamine as a core) was added dropwise. After completion of dropwise addition, the resultant was stirred for 1 h at 5 to 0 C. Then the resultant was subjected to gradual temperature rise and reacted under refluxing for 3 h, the heating was stopped. When the reaction temperature was lowered to 25-30 C., 150 mL of saturated sodium bicarbonate aqueous solution was added, the resultant was stirred for 5 min, and a lower-layer solution was collected through a separating funnel.

(13) (2) 2 mL of nitric acid having a concentration of 98% was added into the above solution, the resultant was stirred at room temperature for 7 min, then 10 g of LiPF.sub.6 was added, the resultant was allowed to react under stirring for 5 h, and then the reaction was stopped. Then 150 mL of saturated sodium bicarbonate aqueous solution was added, the resultant was stirred at room temperature for 5 min, and a lower-layer solution was collected through a separating funnel. To this lower-layer solution, 150 mL of saturated sodium bicarbonate aqueous solution was further added, the resultant was stirred at room temperature for 5 min, and a lower-layer solution was collected through a separating funnel.

(14) (3) After the F113 solvent was removed from the above lower-layer solution through vacuum distillation, 4.5 g of viscous liquid was obtained, which was as a target product.

(15) The obtained product was characterized by infrared spectroscopy, and the positions of individual peaks were substantially the same as those in Example 1.

Example 4

(16) (1) 3 g of D-type perfluoropolyether acyl fluoride (provided by Sinopec Lubricant Co., Ltd., n=8), 1 mL pyridine, and 100 mL of F113 (1,1,2-trifluorotrichloroethane) were added into a 300 mL three-necked flask under stirring. Under a condition of 3 C., 1.5 g of a third generation PAMAM dendrimer (purchased from Weihai Chenyuan Organosilicone New Materials Co., Ltd., trade name: CYD-130A, with p-biphenyldiamine as a core) was added dropwise. After completion of dropwise addition, the resultant was stirred for 1 h at 5 to 0 C. Then the resultant was subjected to gradual temperature rise and reacted under refluxing for 3 h, the heating was stopped. When the reaction temperature was lowered to 25-30 C., 150 mL of saturated sodium bicarbonate aqueous solution was added, the resultant was stirred for 5 min, and a lower-layer solution was collected through a separating funnel.

(17) (2) 2 mL of nitric acid having a concentration of 98% was added into the above solution, the resultant was stirred at room temperature for 7 min, then 14 g of LiAsF.sub.6 was added, the resultant was allowed to react under stirring for 5 h, and then the reaction was stopped. Then 150 mL of saturated sodium bicarbonate aqueous solution was added, the resultant was stirred at room temperature for 5 min, and a lower-layer solution was collected through a separating funnel. To this lower-layer solution, 150 mL of saturated sodium bicarbonate aqueous solution was further added, the resultant was stirred at room temperature for 5 min, and a further lower-layer solution was collected through a separating funnel.

(18) (3) After the F113 solvent was removed from the above lower-layer solution through vacuum distillation, 4.2 g of viscous liquid was obtained, which was as a target product.

(19) The obtained product was characterized by infrared spectroscopy, and the positions of individual peaks were substantially the same as those in Example 1.

Example 5

(20) (1) 3 g of Y-type perfluoropolyether acyl fluoride (provided by Sinopec Lubricant Co., Ltd., n=8), 1 mL triethylamine, and 100 mL of F113 (1,1,2-trifluorotrichloroethane) were added into a 300 mL three-necked flask under stirring. Under a condition of 3 C., 4 g of tri(2-aminoethyl)amine (purchased from Aladdin Reagent Co., Ltd.) was added dropwise. After completion of dropwise addition, the resultant was stirred for 1 h at 5 to 0 C. Then the resultant was subjected to gradual temperature rise and reacted under refluxing for 3 h, the heating was stopped. When the reaction temperature was lowered to 25-30 C., 150 mL of saturated sodium bicarbonate aqueous solution was added, the resultant was stirred for 5 min, and a lower-layer solution was collected through a separating funnel.

(21) (2) 2 mL of nitric acid having a concentration of 98% was added into the above solution, the resultant was stirred at room temperature for 7 min, then 8 g of lithium bistrifluoromethylsulfonimide was added, the resultant was allowed to react under stirring for 5 h, and then the reaction was stopped. Then 150 mL of saturated sodium bicarbonate aqueous solution was added, the resultant was stirred at room temperature for 5 min, and a lower-layer solution was collected through a separating funnel. To this lower-layer solution, 150 mL of saturated sodium bicarbonate aqueous solution was further added, the resultant was stirred at room temperature for 5 min, and a lower-layer solution was collected through a separating funnel.

(22) (3) After the F113 solvent was removed from the above lower-layer solution through vacuum distillation, 3.8 g of viscous liquid was obtained, which was as a target product.

(23) The obtained product was characterized by infrared spectroscopy, and the positions of individual peaks were substantially the same as those in Example 1.

Example 6

(24) (1) 3 g of Y-type perfluoropolyether acyl fluoride (provided by Sinopec Lubricant Co., Ltd., n=8), 1 mL triethylamine, and 100 mL of F113 (1,1,2-trifluorotrichloroethane) were added into a 300 mL three-necked flask under stirring. Under a condition of 3 C., 4.2 g of 1,4-phenylenedimethanamine (purchased from Aladdin Reagent Co., Ltd.) was added dropwise. After completion of dropwise addition, the resultant was stirred for 1 h at 5 to 0 C. Then the resultant was subjected to gradual temperature rise and reacted under refluxing for 3 h, the heating was stopped. When the reaction temperature was lowered to 25-30 C., 150 mL of saturated sodium bicarbonate aqueous solution was added, the resultant was stirred for 5 min, and a lower-layer solution was collected through a separating funnel.

(25) (2) 2 mL of nitric acid having a concentration of 98% was added into the above solution, the resultant was stirred at room temperature for 7 min, then 9 g of BF.sub.4Li was added, the resultant was allowed to react under stirring for 5 h, and then the reaction was stopped. Then 150 mL of saturated sodium bicarbonate aqueous solution was added, the resultant was stirred at room temperature for 5 min, and a lower-layer solution was collected through a separating funnel. To this lower-layer solution, 150 mL of saturated sodium bicarbonate aqueous solution was further added, the resultant was stirred at room temperature for 5 min, and a lower-layer solution was collected through a separating funnel.

(26) (3) After the F113 solvent was removed from the above lower-layer solution through vacuum distillation, 4.1 g of viscous liquid was obtained, which was as a target product.

(27) The obtained product was characterized by infrared spectroscopy, wherein, 3010 cm.sup.1 is an H absorption peak on a benzene ring; 2929.42 cm.sup.1 is a CH.sub.2 absorption peak; 2372.31-2205.32 cm.sup.1 are amine salt absorption peaks; 1821.05 cm.sup.1 is a C(O) absorption peak; 1692.48 cm.sup.1 and 1632.75 cm.sup.1 are C(O)NH absorption peaks; 1460 cm.sup.1, 1500 cm.sup.1 and 1600 cm.sup.1 are benzene ring absorption peaks; and 1116.10 cm.sup.1 is a tertiary amine absorption peak.

Application Example 1

(28) (1) A friction and wear test was conducted on a fluorine oil (provided by Sinopec Lubricant Co., Ltd., a fluoric vacuum pump oil) by using an HFRR instrument under the following test conditions: ball/disc friction pair, 200 g, 80 Hz, 90 C., 1 h, 1 mm. The measured average friction coefficient was 0.122, the measured disc wear volume was 1.295*10.sup.6 m.sup.3, and the measured disc wear rate was 0.144*10.sup.6 mm.sup.2/gs.

(29) (2) 3 g of the lubricating oil friction modifier from Example 1 was added to 97 g of fluorine oil (provided by Sinopec Lubricant Company, a fluoric vacuum pump oil). A friction and wear test was conducted on the resultant by using an HFRR instrument under the following test conditions: ball/disc friction pair, 200 g, 80 Hz, 90 C., 1 h, 1 mm. The measured average friction coefficient was 0.118, the measured disc wear volume was 7.18*10.sup.5 m.sup.3, and the measured disc wear rate was 0.0798*10.sup.6 mm.sup.2/gs.

(30) Compared with a single fluorine oil, the fluorine oil added with 3% of the lubricating oil friction modifier had a slightly reduced friction coefficient, but its disc wear rate was significantly reduced by 44.58%. Thus it can be seen that, the fluorine oil added with the prepared lubricating oil friction modifier had a significantly improved wear resistance.

Application Example 2

(31) (1) A friction and wear test was conducted on a fluorine oil (provided by Sinopec Lubricant Co., Ltd., an FM 110 shielding oil for coating) by using an HFRR instrument under the following test conditions: ball/disc friction pair, 200 g, 80 Hz, 90 C., 1 h, 1 mm. The measured average friction coefficient was 0.122, the measured disc wear volume was 1.295*10.sup.6 m.sup.3, and the measured disc wear rate was 0.144*10.sup.6 mm.sup.2/gs.

(32) (2) 5 g of the lubricating oil friction modifier from Example 2 was added to 95 g of fluorine oil (provided by Sinopec Lubricant Co., Ltd., an FM 110 shielding oil for coating). A friction and wear test was conducted on the resultant by using an HFRR instrument under the following test conditions: ball/disc friction pair, 200 g, 80 Hz, 90 C., 1 h, 1 mm. The measured average friction coefficient was 0.115, the measured disc wear volume was 6.77*10.sup.5 m.sup.3, and the measured disc wear rate was 0.0752*10.sup.6 mm.sup.2/gs.

(33) Compared with a single fluorine oil, the fluorine oil added with 5% of the lubricating oil friction modifier had a slightly reduced friction coefficient, but its disc wear rate was significantly reduced by 47.78%. Thus it can be seen that, the fluorine oil added with the prepared lubricating oil friction modifier had a significantly improved wear resistance.

Application Example 3

(34) (1) A friction and wear test was conducted on a fluorine grease (provided by Sinopec Lubricant Co., Ltd., a high temperature resistant lubricating grease) by using an HFRR instrument under the following test conditions: ball/disc friction pair, 200 g, 50 Hz, 90 C., 1 h, 2 mm. The measured average friction coefficient was 0.142, and the measured diameter of disc wear spot was 126 m.

(35) (2) 8 g of the lubricating oil friction modifier from Example 3 was added to 92 g of the fluorine grease (provided by Sinopec Lubricant Co., Ltd., a high temperature resistant lubricating grease). A friction and wear test was conducted on the resultant by using an HFRR instrument under the following test conditions: ball/disc friction pair, 200 g, 50 Hz, 90 C., 1 h, 2 mm. The measured average friction coefficient was 0.115, and the measured diameter of disc wear spot was 92 m.

(36) Compared with a single fluorine grease, the fluorine grease added with 8% of the lubricating oil modifier had a friction coefficient and a diameter of disc wear spot significantly reduced by 19.01% and 26.98%, respectively. Thus it can be seen that, the fluorine grease added with the prepared lubricating oil friction modifier had a significantly improved friction and wear resistance.

Application Example 4

(37) (1) A friction and wear test was conducted on a fluorine grease (provided by Sinopec Lubricant Co., Ltd., a high temperature resistant lubricating grease) by using an HFRR instrument under the following test conditions: ball/disc friction pair, 200 g, 50 Hz, 90 C., 1 h, 2 mm. The measured average friction coefficient was 0.142, and the measured diameter of disc wear spot was 126 m.

(38) (2) 9 g of the lubricating oil friction modifier from Example 4 was added to 91 g of the fluorine grease (provided by Sinopec Lubricant Co., Ltd., a high temperature resistant lubricating grease). A friction and wear test was conducted on the resultant by using an HFRR instrument under the following test conditions: ball/disc friction pair, 200 g, 50 Hz, 90 C., 1 h, 2 mm. The measured average friction coefficient was 0.108, and the measured diameter of disc wear spot was 87 m.

(39) Compared with a single fluorine grease, the fluorine grease added with 9% of the lubricating oil modifier had a friction coefficient and a diameter of disc wear spot significantly reduced by 23.94% and 30.95%, respectively. Thus it can be seen that, the fluorine grease added with the prepared lubricating oil friction modifier had a significantly improved friction and wear resistance.

Application Example 5

(40) (1) A friction and wear test was conducted on a fluorine oil (provided by Sinopec Lubricant Co., Ltd., an FM 110 shielding oil for coating) by using an HFRR instrument under the following test conditions: ball/disc friction pair, 200 g, 80 Hz, 90 C., 1 h, 1 mm. The measured average friction coefficient was 0.122, the measured disc wear volume was 1.295*10.sup.6 m.sup.3, and the measured disc wear rate was 0.144*10.sup.6 mm.sup.2/gs.

(41) (2) 10 g of the lubricating oil friction modifier from Example 5 was added to 90 g of the fluorine oil (provided by Sinopec Lubricant Co., Ltd., an FM 110 shielding oil for coating). A friction and wear test was conducted on the resultant by using an HFRR instrument under the following test conditions: ball/disc friction pair, 200 g, 80 Hz, 90 C., 1 h, 1 mm. The measured average friction coefficient was 0.112, the measured disc wear volume was 7.87*10.sup.5 m.sup.3, and the measured disc wear rate was 0.0874*10.sup.6 mm.sup.2/gs.

(42) Compared with a single fluorine oil, the fluorine oil added with 10% of the lubricating oil friction modifier had a slightly reduced friction coefficient, but its disc wear rate was significantly reduced by 39.28%. Thus it can be seen that, the fluorine oil added with the prepared lubricating oil friction modifier had a significantly improved wear resistance.

Application Example 6

(43) (1) A friction and wear test was conducted on a fluorine oil (provided by Sinopec Lubricant Co., Ltd., an FM 110 shielding oil for coating) by using an HFRR instrument under the following test conditions: ball/disc friction pair, 200 g, 80 Hz, 90 C., 1 h, 1 mm. The measured average friction coefficient was 0.122, the measured disc wear volume was 1.295*10.sup.6 m.sup.3, and the measured disc wear rate was 0.144*10.sup.6 mm.sup.2/gs.

(44) (2) 1 g of the lubricating oil friction modifier from Example 6 was added to 95 g of the fluorine oil (provided by Sinopec Lubricant Co., Ltd., an FM 110 shielding oil for coating). A friction and wear test was conducted on the resultant by using an HFRR instrument under the following test conditions: ball/disc friction pair, 200 g, 80 Hz, 90 C., 1 h, 1 mm. The measured average friction coefficient was 0.117, the measured disc wear volume was 9.87*1105 m.sup.3, and the measured disc wear rate was 0.0874*10.sup.6 mm.sup.2/gs.

(45) Compared with a single fluorine oil, the fluorine oil added with 1% of the lubricating oil friction modifier had a slightly reduced friction coefficient, but its disc wear rate was significantly reduced by 23.84%. Thus it can be seen that, the fluorine oil added with the prepared lubricating oil friction improver had a significantly improved wear resistance.

(46) As to any numerical value mentioned in the present invention, if there is only a two-unit interval between any lowest value and any highest value, it includes all the values obtained by increasing by one unit each time from the lowest value to the highest value. For example, if it is claimed that an amount of a component, or a value of a process variable such as temperature, pressure, time, etc. is 50-90, it means that values such as 51-89, 52-88 . . . , 69-71, 70-71, etc. are specifically enumerated in the description. As to non-integer values, it is appropriate to consider using 0.1, 0.01, 0.001, or 0.0001 as one unit. These are only some specially specified examples. In the present application, likewise, all the possible combinations of the enumerated values between a lowest value and a highest value are considered to have been disclosed.

(47) It should be noted that, the examples described above are only used to explain the present invention, but do not constitute any limitation on the present invention. The present invention has been described by referring to typical examples, but it should be understood that the words used herein are descriptive and explanatory vocabularies, rather than restrictive vocabularies. Modifications may be made to the present invention within the scope of the claims of the present invention as required, and revisions may be made without departing from the scope and spirit of the present invention. Although the present invention described herein relates to specific methods, materials, and examples, but it is not meant that the present invention is limited to the specific examples disclosed herein. On the contrary, the present invention may be extended to all the other methods and applications with the same functionality.