Alkanolamine, friction-reducing agent, and lubricating oil composition

Abstract

To provide a friction-reducing agent containing no sulfur nor phosphorus and being excellent in friction-reducing properties, and a lubricating oil composition using it. An alkanolamine represented by the following formula is used as a friction-reducing agent: ##STR00001##
wherein A.sub.1 and A.sub.2 are each independently a hydroxy group or a hydrogen atom, provided that A.sub.1 and A.sub.2 are not hydrogen atoms at the same time, R.sub.1 is a hydrocarbon group having at most 30 carbon atoms, R.sub.2 to R.sub.6 are each independently a hydrogen atom or a hydrocarbon group having at most 30 carbon atoms, and m and n are each independently an integer of from 0 to 10.

Claims

1. A method for producing an alkanolamine represented by the following formula (1): ##STR00026## wherein A.sub.1 and A.sub.2 are hydroxy groups, R.sub.1 is a hydrocarbon group having at least 8 and at most 24 carbon atoms, R.sub.2 to R.sub.6 are hydrogen atoms, and m is 1 and n is 0, the method comprising reacting a raw material amine represented by the following formula with a halide represented by the following formula or an epoxy compound represented by the following formula and further with a halide represented by the following formula: ##STR00027## wherein R.sub.2 to R.sub.5 are hydrogen atoms; ##STR00028## wherein A.sub.1 and A.sub.2 are hydroxy groups, R.sub.6 is a hydrogen atom, X is a halogen atom, and m is 1 and n is 0; ##STR00029## wherein A.sub.2 is a hydroxy group, R.sub.6 is a hydrogen atom, and n is 0;
R.sub.1X(5) wherein R.sub.1 is a hydrocarbon group having at least 8 and at most 24 carbon atoms, and X is a halogen atom.

2. A method for producing an alkanolamine represented by the following formula (1): ##STR00030## wherein A.sub.1 and A.sub.2 are hydroxy groups, R.sub.1 is a hydrocarbon group having at least 8 and at most 24 carbon atoms, R.sub.2 to R.sub.6 are hydrogen atoms, and m is 1 and n is 0, the method comprising reacting a raw material amine represented by the following formula with a halide represented by the following formula and further with a halide represented by the following formula or an epoxy compound represented by the following formula: ##STR00031## wherein R.sub.2 to R.sub.5 are hydrogen atoms;
R.sub.1X(5) wherein R.sub.1 is a hydrocarbon group having at least 8 and at most 24 carbon atoms, and X is a halogen atom; ##STR00032## wherein A.sub.1 and A.sub.2 are hydroxy groups, R.sub.6 is a hydrogen atom, X is a halogen atom, and m is 1 and n is 0; ##STR00033## wherein A.sub.2 is a hydroxy group, R.sub.6 is a hydrogen atom, and n is 0.

Description

DESCRIPTION OF EMBODIMENTS

(1) Now, the present invention will be described in further detail.

(2) The alkanolamine of the present invention is characterized by being represented by the formula (1).

(3) In the formula (1), A.sub.1 and A.sub.2 are each independently a hydroxy group or a hydrogen atom, and A.sub.1 and A.sub.2 are not hydrogen atoms at the same time. With a view to obtaining favorable friction-reducing properties, A.sub.1 and A.sub.2 in the formula (1) are particularly preferably both hydroxy groups.

(4) In the formula (1), R.sub.1 is a hydrocarbon group having at most 30 carbon atoms, and R.sub.2 to R.sub.6 are each independently a hydrogen atom or a hydrocarbon group having at most 30 carbon atoms.

(5) The hydrocarbon having at most 30 carbon atoms may, for example, be an alkyl group, an alkenyl group, an aryl group, a cycloalkyl group or a cycloalkenyl group, having at most 30 carbon atoms.

(6) The alkyl group having at most 30 carbon atoms may, for example, be a methyl group, an ethyl group, or a linear or branched propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, eicosyl group, heneicosyl group, docosyl group, tricosyl group or tetracosyl group.

(7) The alkenyl group having at most 30 carbon atoms may, for example, be a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group, a decenyl group, an undecenyl group or a dodecenyl group.

(8) The aryl group having at most 30 carbon atoms may, for example, be a phenyl group, a toluyl group, a xylyl group, a cumenyl group, a mesityl group, a benzyl group, a phenethyl group, a styryl group, a cinnamyl group, a benzhydryl group, a trityl group, an ethylphenyl group, a propylphenyl group, a butylphenyl group, a pentylphenyl group, a hexylphenyl group, a heptylphenyl group, an octylphenyl group, a nonylphenyl group, a decylphenyl group, an undecylphenyl group, a dodecylphenyl group, a styrenated phenyl group, a p-cumylphenyl group, a phenylphenyl group, a benzylphenyl group, an -naphthyl group or a -naphthyl group.

(9) The cycloalkyl group and cycloalkenyl group, having at most 30 carbon atoms, may, for example, be a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a methylcyclopentyl group, a methylcyclohexyl group, a methylcycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a methylcyclopentenyl group, a methylcyclohexenyl group or a methylcycloheptenyl group.

(10) Among these hydrocarbon groups, R.sub.1 to R.sub.6 are preferably an alkyl group having at most 30 carbon atoms, more preferably a C.sub.8-24 alkyl group.

(11) It is preferred that all of R.sub.2 to R.sub.6 are hydrogen atoms, in view of easy preparation of the alkanolamine.

(12) R.sub.1 is, in view of excellent oil solubility of the alkanolamine, preferably a C.sub.8-24 alkyl group, more preferably an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an eicosyl group, a heneicosyl group, a docosyl group, a tricosyl group or a tetracosyl group.

(13) In the formula (1), m and n represent the number of methylene groups, and are each independently an integer of from 0 to 10. It is preferred that m and n are each independently an integer of from 0 to 3, and in view of excellent friction-reducing properties, it is particularly preferred that m=1 and n=0.

(14) The alkanolamine in the present invention may, for example, be specifically 3-(4-octyl-1-piperazinyl)-1,2-propanediol, 3-(4-(2-ethylhexyl)-1-piperazinyl)-1,2-propanediol, 3-(4-nonyl-1-piperazinyl)-1,2-propanediol, 3-(4-decyl-1-piperazinyl)-1,2-propanediol, 3-(4-undecyl-1-piperazinyl)-1,2-propanediol, 3-(4-dodecyl-1-piperazinyl)-1,2-propanediol, 3-(4-tridecyl-1-piperazinyl)-1,2-propanediol, 3-(4-tetradecyl-1-piperazinyl)-1,2-propanediol, 3-(4-hexadecyl-1-piperazinyl)-1,2-propanediol, 3-(4-heptadecyl-1-piperazinyl)-1,2-propanediol, 3-(4-octadecyl-1-piperazinyl)-1,2-propanediol, 3-(4-nonadecyl-1-piperazinyl)-1,2-propanediol, 3-(4-eicosyldecyl-1-piperazinyl)-1,2-propanediol, 3-(4-heneicosyldecyl-1-piperazinyl)-1,2-propanediol, 3-(4-docosyl-1-piperazinyl)-1,2-propanediol, 3-(4-tricosyl-1-piperazinyl)-1,2-propanediol, 3-(4-tetracosyl-1-piperazinyl)-1,2-propanediol, 3-(4-phenyl-1-piperazinyl)-1,2-propanediol, 3-(4-benzyl-1-piperazinyl)-1,2-propanediol, 3-(4-cyclohexyl-1-piperazinyl)-1,2-propanediol, 4-(4-dodecyl-1-piperazinyl)-1,2-butanediol, 4-(4-dodecyl-1-piperazinyl)-1,3-butanediol, 4-(4-dodecyl-1-piperazinyl)-2,3-butanediol, 5-(4-dodecyl-1-piperazinyl)-1,2-pentanediol, 6-(4-dodecyl-1-piperazinyl)-1,2-hexanediol, 8-(4-dodecyl-1-piperazinyl)-1,2-octanediol, 4-dodecyl-1-piperazineethanol, 4-dodecyl-1-piperazinepropanol, 3-(4-(2-octyldodecyl)-1-piperazinyl)-1,2-propanediol, 3-(4-(2-hexyldecyl)-1-piperazinyl)-1,2-propanediol, 3-(4-(2-decyltetradecyl)-1-piperazinyl)-1,2-propanediol, 3-(4-isostearyl-1-piperazinyl)-1,2-propanediol or 3-(4-oleyl-1-piperazinyl)-1,2-propanediol.

(15) The alkanolamine of the present invention may be produced by reacting a raw material alkanolamine with a halide or an epoxy compound. Further, the raw material alkanolamine may be produced by reacting a raw material amine with a halide containing a hydroxy group or an epoxy compound.

(16) In the above reaction, the reaction temperature is not particularly limited, however, with a view to obtaining a desired product with a favorable yield, it is preferably from 40 C. to 200 C., particularly preferably from 60 C. to 150 C.

(17) For the reaction, a solvent may be used. The solvent is not particularly limited and may, for example, be a hydrocarbon organic solvent such as hexane, cyclohexane, octane, isooctane, benzene, toluene, xylene or paraffin, an alcohol organic solvent such as methanol, ethanol, isopropanol, butanol, ethylene glycol or propylene glycol, or an aprotic polar solvent such as diethyl ether, dibutyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran, dimethylformamide or dimethylsufoxide. They may be used alone or as a mixture of two or more.

(18) For the reaction, a catalyst may be used. The catalyst is not particularly limited and may, for example, be an alkali metal carbonate such as potassium carbonate, sodium carbonate, lithium carbonate or cesium carbonate, an alkaline earth metal carbonate such as magnesium carbonate or calcium carbonate, an alkali metal hydrogen carbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate, an alkali metal hydroxide such as sodium hydroxide, potassium hydroxide or lithium hydroxide, an alkaline earth metal hydroxide such as magnesium hydroxide or calcium hydroxide, or a basic substance such as sodium methoxide or sodium ethoxide.

(19) The raw material amine used for production of the alkanolamine of the present invention is not particularly limited and may, for example, be piperazine or a piperazine derivative. Specifically, although it is not particularly limited, it may, for example, be piperazine, 2-methyl-piperazine, 1-octyl-piperazine, 1-(2-ethylhexyl)-piperazine, 1-nonyl-piperazine, 1-decyl-piperazine, 1-undecyl-piperazine, 1-dodecyl-piperazine, 1-tridecyl-piperazine, 1-tetradecyl-piperazine, 1-tetradecyl-piperazine, 1-hexadecyl-piperazine, 1-heptadecyl-piperazine, 1-octadecyl-piperazine, 1-nonadecyl-piperazine, 1-eicosyldecyl-piperazine, 1-heneicosyldecyl-piperazine, 1-docosyl-piperazine, 1-tricosyl-piperazine, 1-tetracosyl-piperazine, 1-phenyl-piperazine, 1-benzyl-piperazine or 1-cyclohexyl-piperazine.

(20) The raw material alkanolamine used for production of the alkanolamine of the present invention is not particularly limited and may, for example, be 3-(1-piperazinyl)-1, 2-propanediol, 4-(1-piperazinyl)-1, 3-butanediol, 4-(1-piperazinyl)-2, 3-butanediol, 5-(1-piperazinyl)-1, 2-pentanediol, 6-(1-piperazinyl)-1, 2-hexanediol, 8-(1-piperazinyl)-1, 2-octanediol, 1-piperazinemethanol, 1-piperazineethanol, 1-piperazinepropanol, 1-piperazinebutanol, 1-piperazinepentanol, 1-piperazinehexanol, 1-piperazineheptanol or 1-piperazineoctanol.

(21) The halide used for production of the alkanolamine of the present invention is not particularly limited and may, for example, be a brominated hydrocarbon, chlorinated hydrocarbon, iodinated hydrocarbon or fluorinated hydrocarbon, having at most 30 carbon atoms, and they may have one or two hydroxy groups in its molecule.

(22) The epoxy compound used for production of the alkanolamine of the present invention is not particularly limited and may be an epoxy hydrocarbon group having at most 10 carbon atoms, and may have one hydroxy group in its molecule. It may, for example, be specifically, glycidol, ethylene oxide or propylene oxide.

(23) After completion of the reaction, the alkanolamine of the present invention can be obtained by means of a conventional purification method such as extraction, filtration, crystallization, distillation or chromatography by itself or suitably in combination.

(24) A specific method for producing the alkanolamine of the present invention is not particularly limited and may, for example, be a method of reacting a raw material amine represented by the following formula (2) with a halide represented by the following formula (3) or an epoxy compound represented by the following formula (4) and further with a halide represented by the following formula (5) or a method of reacting a raw material amine represented by the following formula (2) with a halide represented by the following formula (5) and further with a halide represented by the following formula (3) or an epoxy compound represented by the following formula (4).

(25) ##STR00010##
wherein R.sub.2 to R.sub.5 are each independently a hydrogen atom or a hydrocarbon group having at most 30 carbon atoms;

(26) ##STR00011##
wherein A.sub.1 and A.sub.2 are each independently a hydroxy group or a hydrogen atom, provided that A.sub.1 and A.sub.2 are not hydrogen atoms at the same time, R.sub.6 is a hydrogen atom or a hydrocarbon group having at most 30 carbon atoms, X is a halogen atom, and m and n are each independently an integer of from 0 to 10;

(27) ##STR00012##
wherein A.sub.2 is a hydroxy group or a hydrogen atom, R.sub.6 is a hydrogen atom or a hydrocarbon group having at most 30 carbon atoms, and n is an integer of from 0 to 10;
R.sub.1X(5)
wherein R.sub.1 is a hydrocarbon group having at most 30 carbon atoms, and X is a halogen atom.

(28) In the formulae (3) and (5), X is a halogen atom, and the halogen atom is not particularly limited and may, for example, be a bromine atom, a chlorine atom, an iodine atom or a fluorine atom.

(29) The alkanolamine compound of the present invention may be used as a composition or an additive of a lubricating oil. A composition containing the alkanolamine of the present invention and a molybdenum compound may be used as a friction-reducing agent for a lubricating oil, although it is not particularly limited.

(30) The friction-reducing agent of present invention is preferably a composition containing the above alkanolamine and a molybdenum compound, and the composition preferably contains the molybdenum compound in a content of from 0.1 to 3 mol as calculated as molybdenum atoms in the molybdenum compound per 1 mol of the alkanolamine. The molybdenum content is, in view of excellent friction-reducing properties, preferably from 0.5 to 1.5 mol. If the amount of the molybdenum atoms is less than 0.1 mol, no satisfactory friction-reducing properties will be obtained, and if it exceeds 3 mol, the oil solubility may decrease.

(31) The molybdenum compound in the friction-reducing agent of the present invention is a compound having molybdenum in its molecule and is not particularly limited. It may, for example, be molybdenum trioxide, molybdic acid, an alkali metal molybdate or ammonium molybdate. They may be used alone or as a mixture of two or more. Considering the oil solubility and friction properties, among them, molybdenum trioxide is particularly preferred.

(32) The method for producing the friction-reducing agent of the present invention is not particularly limited and may, for example, be a method of mixing the alkanolamine of the present invention and the molybdenum compound in a content of the molybdenum compound of from 0.1 to 3 mol as calculated as molybdenum atoms in the molybdenum compound per 1 mol of the alkanolamine, and heating the mixture. The temperature at the time of heating is not particularly limited, and is preferably from 40 C. to 200 C., particularly preferably from 60 C. to 120 C., whereby a composition having favorable oil solubility is obtained. In the method, a solvent may be used, and a solvent which can be used is not particularly limited and may, for example, be a hydrocarbon organic solvent such as hexane, cyclohexane, octane, isooctane, benzene, toluene, xylene or paraffin, an alcohol organic solvent such as methanol, ethanol, isopropanol, butanol, ethylene glycol or propylene glycol, an aprotic polar solvent such as diethylene ether, dibutyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran, dimethylformamide or dimethylsulfoxide, a fuel oil such as gasoline, gas oil, kerosene, mineral oil or polybutene, a lubricating oil such as a mineral oil, a synthetic oil, a vegetable oil or an animal oil (including an unmixed lubricating oil, and a lubricating oil containing additives such as a detergent dispersant, an antioxidant, a load carrying additive, a rust inhibitor, a corrosion inhibitor, a viscosity index improver, a pour point depressant, an anti-foam additive, an emulsifying agent, an anti-emulsifying agent, and a microbiocide), or water. They may be used alone or as a mixture of two or more.

(33) In production of the friction-reducing agent of the present invention, after mixing and heating, as the case requires, the solvent may be removed e.g. by vacuum distillation, or the mixture may be used as it is without removing the solvent.

(34) The lubricating oil composition of the present invention is characterized by containing the friction-reducing agent of the present invention and the lubricating oil (including an unmixed lubricating oil and a lubricating oil containing additives). The lubricating oil is not particularly limited and may, for example, be an automobile lubricating oil such as a gasoline engine oil, a Diesel engine oil or a vehicle gear oil, a ship lubricating oil such as a ship engine oil, or an industrial lubricating oil such as a machine oil, a metal processing oil or an electrical insulating oil.

(35) The lubricating oil composition of the present invention may contain an abrasion inhibitor other than the friction-reducing agent of the present invention, within a range not to impair the effects of the present invention, whereby the lubricating oil composition will have more favorable friction-reducing properties. Such an abrasion inhibitor is preferably a zinc dithiophosphate abrasion inhibitor, and may, for example, be zinc dialkyldithiophosphate, zinc diaryldithiophosphate or zinc alkylaryldithiophosphate. As commercial products, specifically, Lz 677A, Lz 1095, Lz 1097, Lz 1370, Lz 1371, Lz 1373 and Lz 1395 commercially available from The Lubrizol Corporation, OLOA 260, OLOA 262, OLOA 267 and OLOA 269R commercially available from Chevron Oronite, HITEC 7169 and HITEC 7197 commercially available from Afton Chemical Corporation, and ADEKA KIKU-LUBE Z-112 available from ADEKA CORPORATION.

(36) The friction-reducing agent of the present invention may further contain a boron compound, whereby more favorable friction-reducing properties at low temperature will be obtained. The boron compound used is not particularly limited and may, for example, be an aminoborane compound such as tris(dimethylamino)borane or tris(diethylamino)borane, a borate ester such as trimethyl borate, triethyl borate, tripropyl borate, tributyl borate, tripentyl borate, trihexyl borate, trioctyl borate, tridecyl borate, tritetradecyl borate, triphenyl borate, triethanolamine borate, triisopropanolamine borate, 2-ethoxy-4,4,5,5-tetramethyl-1,3,2-dioxoborolane, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxoborolane, 2-isopropoxy-4,4,6-trimethyl-1,3,2-dioxaborinane, 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxoborolane, 2,4,6-trimethylboroxine, tris(trimethylsilyl)borate or tris(2-cyanoethyl)borate, a boronic acid compound such as ethyl boronate, propyl boronate, butyl boronate, pentyl boronate, hexyl boronate, octyl boronate, decyl boronate, dodecyl boronate, tridecyl boronate, tetradecyl boronate, cyclohexyl boronate, cyclopentyl boronate or 1-cyclopentenyl boronate, or a boron dispersed alkenyl succinimide. The amount of the boron compound blended (that is, the content in the friction-reducing agent) is preferably within a range of from 0.01 to 3.0 wt %, particularly preferably within a range of from 0.05 to 2.0 wt %, in view of excellent balance between the friction-reducing properties particularly at low temperature and oil solubility.

EXAMPLES

(37) Now, the present invention will be described in further detail with reference to Examples. However, it should be understood that the present invention is by no means restricted to such specific Examples. Reagents etc. used were commercial products unless otherwise specified.

(38) Analytical instruments and evaluation methods employed in Examples are described below.

(39) <NMR Measurement>

(40) NMR measuring apparatus: VARIAN Gemini-200.

(41) <Elemental Analysis>

(42) Elemental analyzer: automatic elemental analysis apparatus 240011, manufactured by Perkin Elmer Japan Co., Ltd.

(43) Oxygen flask combustion IC measurement method: Ion Chromatograph IC-2001 manufactured by TOSOH CORPORATION.

(44) <Evaluation of Oil Solubility>

(45) The obtained amine molybdate composition was mixed with toluene so that the concentration of the amine molybdate concentration would be 1 wt %, followed by stirring with heating at 80 C. for dissolution. The state of the solution after left to stand overnight was visually observed and taken as the index of the oil solubility.

(46) (Evaluation standard)

(47) A: A solution state without precipitates or suspension.

(48) B: A suspension state.

(49) C: A state with separation or precipitates observed.

(50) <Evaluation of Friction Properties>

(51) The obtained friction-reducing agent was blended with base oil (C-1, manufactured by Exxon Mobil Corporation, SpectraSyn Plus 6) so that the molybdenum concentration would be 500 ppm. Further, zinc dialkyldithiophosphate (ZnDTP, manufactured by ADEKA CORPORATION, KIKU-LUBE Z-112) as an abrasion inhibitor was blended so that the zinc concentration would be 1,000 ppm.

(52) Of a blended oil prepared in the after-described Examples, the coefficient of friction was evaluated by using Friction Player (manufactured by RHESCA CO., LTD., FPR2100) by ball-on-disk method at 120 C. at a rotational speed of 477.5 rpm under a load of 10 N. For the ball and the disk, lapped SUJ2 was used. The average of coefficients of friction measured for one hour was calculated.

(53) (Evaluation Standards)

(54) A: Coefficient of friction being less than 0.075.

(55) B: Coefficient of friction being at least 0.075 and less than 0.10.

(56) C: Coefficient of friction being at least 0.10.

(57) <Evaluation of Low Temperature Friction Properties>

(58) Of a blended oil prepared in the after-described Examples, the coefficient of friction was evaluated by using Friction Player (manufactured by RHESCA CO., LTD., FPR2100) by ball-on-disk method at 80 C. at a rotational speed of 477.5 rpm under a load of 10 N. For the ball and the disk, lapped SUJ2 was used. The average of coefficients of friction measured for 3 hours was calculated.

(59) (Evaluation Standards)

(60) A: Coefficient of friction being less than 0.075.

(61) B: Coefficient of friction being at least 0.075 and less than 0.10.

(62) C: Coefficient of friction being at least 0.10.

Example 1

(63) Into a 1 L four-necked flask equipped with a stirring machine and a condenser tube, 74.4 g (0.47 mol) of 3-(1-piperazinyl)-1,2-propanediol, 38.6 g (0.16 mol) of dodecyl bromide, isopropanol (500 g) and 17.3 g (0.16 mol) of sodium carbonate were added, followed by heating at 90 C. for 8 hours in a stream of nitrogen. After completion of heating, sodium carbonate was removed by filtration, and 2-propanol was removed by vacuum distillation. Then, only the oil layer was collected by extraction with chloroform, which was subjected to vacuum distillation and vacuum drying to obtain 48.58 g (yield: 95.4%) of white crystalline 3-(4-dodecyl-1-piperazinyl)-1,2-propanediol. Identification was conducted from the results of .sup.1H-NMR measurement, .sup.13C-NMR measurement and elemental analysis.

(64) .sup.1H-NMR (CDCl.sub.3): 3.72-3.84 (m, 2H), 3.48-3.53 (dd, 1H), 2.29-2.70 (m, 12H), 1.47 (s, 2H), 1.19-1.26 (m, 18H), 0.86-0.90 (t, 3H) [ppm]

(65) .sup.13C-NMR (CDCl.sub.3): 66.85, 65.00, 60.44, 58.73, 53.35, 53.23, 31.86, 29.61, 29.58, 29.56, 29.53, 29.29, 27.56, 26.81, 22.63, 14.05 [ppm]

(66) Elemental analysis (calculated value): C=69.5, H=12.3, N=8.5,

(67) Elemental analysis (measured value): C=69.6, H=12.8, N=8.5.

(68) Then, into a 100 mL round bottom flask, 3.29 g of 3-(4-dodecyl-1-piperazinyl)-1,2-propanediol and 10 g of toluene were added, followed by heating at 80 C. for dissolution, and an aqueous molybdenum dispersion having 1.51 g of molybdenum trioxide dispersed in 10 g of water was dropwise added. On that occasion, the Mo atom/amine (molar ratio) was 1.05. Then, the reaction mixture was aged at 80 C. for 2 hours and at 110 C. for 1 hour. After completion, unreacted molybdenum trioxide was removed by filtration, and the solvent was removed by vacuum distillation and vacuum drying to obtain 3.58 g of liver brown solid friction-reducing agent (A-1). The molybdenum content in the friction-reducing agent (A-1) was 13.2 wt %.

(69) Using the obtained friction-reducing agent (A-1), oil solubility and friction properties were evaluated, and the results are shown in Table 1. The friction-reducing agent (A-1) was excellent in oil solubility, had a low coefficient of friction and had favorable friction-reducing properties.

(70) TABLE-US-00001 TABLE 1 Example 1 Example 2 Friction-reducing A-1 A-2 agent Amine Name 3-(4-dodecyl-1- 3-(4-hexadecyl-1- piperazinyl)-1,2- piperazinyl)-1,2- propanediol propanediol Structural formula Molybdenum MoO.sub.3 MoO.sub.3 Mo/amine (molar ratio) 1.05 0.5 Mo content (wt %) 13.2 9.3 Oil solubility Results Soluble Soluble Evaluation A A Friction Coefficient 0.052 0.044 properties of friction Evaluation A A Example 3 Example 4 Friction-reducing A-3 A-4 agent Amine Name 3-(4-octadecyl-1- 3-(4-dodecyl-1- piperazinyl)-1,2- piperazinyl)-1,2- propanediol propanediol Structural formula Molybdenum MoO.sub.3 MoO.sub.3 Mo/amine (molar ratio) 1.05 1.5 Mo content (wt %) 8.2 21.7 Oil solubility Results Soluble Soluble Evaluation A A Friction Coefficient 0.072 0.069 properties of friction Evaluation A A

(71) TABLE-US-00002 TABLE 2 Example 5 Example 6 Friction- A-5 A-6 reducing agent Amine Name 3-(4-(2-ethylhexyl)-1- 4-dodecyl-1- piperazinyl)-1,2- piperazineethanol propanediol Structural formula Molybdenum MoO.sub.3 MoO.sub.3 Mo/amine (molar ratio) 1.05 1.05 Mo content (wt %) 16.3 6.4 Oil solubility Results Soluble Soluble Evaluation A A Friction Coefficient 0.089 0.066 properties of friction Evaluation B A Example 7 Example 8 Friction- A-7 A-8 reducing agent Amine Name 3-(4-(2-decyltetradecyl)-1- 3-(4-(2-decyltetradecyl)-1- piperazinyl)-1,2- piperazinyl)-1,2- propanediol propanediol Structural formula 0 Molybdenum MoO.sub.3 MoO.sub.3 Mo/amine (molar ratio) 1.05 0.75 Mo content (wt %) 12.7 8.8 Oil solubility Results Soluble Soluble Evaluation A A Friction Coefficient 0.045 0.51 properties of friction Evaluation A A

Example 2

(72) Into a 1 L four-necked flask equipped with a stirring machine and a condenser tube, 74.4 g (0.47 mol) of 3-(1-piperazinyl)-1,2-propanediol, 47.3 g (0.16 mol) of hexadecyl bromide, isopropanol (500 g) and 17.3 g (0.16 mol) of sodium carbonate were added, followed by heating at 90 C. for 8 hours in a stream of nitrogen. After completion of heating, sodium carbonate was removed by filtration, and 2-propanol was removed by vacuum distillation. Then, only the oil layer was collected by extraction with chloroform, which was subjected to vacuum distillation and vacuum drying to obtain 56.6 g (yield: 94.9%) of white crystalline 3-(4-hexadecyl-1-piperazinyl)-1,2-propanediol.

(73) Identification was conducted from the results of .sup.1H-NMR measurement, .sup.13C-NMR measurement and elemental analysis.

(74) .sup.1H-NMR (CDCl.sub.3): 3.72-3.86 (m, 2H), 3.43-3.54 (dd, 1H), 2.34-2.75 (m, 12H), 1.50 (s, 2H), 1.19-1.26 (m, 26H), 0.86-0.90 (t, 3H) [ppm].

(75) .sup.13C-NMR (CDCl.sub.3): 67.25, 65.26, 60.76, 58.89, 53.28, 32.16, 29.93, 29.90, 29.85, 29.82, 29.79, 29.60, 27.78, 26.88, 22.92, 14.36 [ppm].

(76) Elemental analysis (calculated value): C=71.8, H=12.6, N=7.3,

(77) Elemental analysis (measured value): C=71.8, H=12.8, N=7.3.

(78) Then, into a 100 mL round bottom flask, 3.85 g of 3-(4-hexadecyl-1-piperazinyl)-1,2-propanediol and 10 g of toluene were added, followed by heating at 80 C. for dissolution, and an aqueous molybdenum dispersion having 0.72 g of molybdenum trioxide dispersed in 10 g of water was dropwise added. On that occasion, the Mo atom/amine (molar ratio) was 0.5. Then, the reaction mixture was aged at 80 C. for 2 hours and at 110 C. for 1 hour. After completion, unreacted molybdenum trioxide was removed by filtration, and the solvent was removed by vacuum distillation and vacuum drying to obtain 4.35 g of deep green solid friction-reducing agent (A-2). The molybdenum content in the friction-reducing agent (A-2) was 9.2 wt %.

(79) Using the obtained friction-reducing agent (A-2), oil solubility and friction properties were evaluated, and the results are shown in Table 1. The friction-reducing agent (A-2) was excellent in oil solubility, had a low coefficient of friction and had favorable friction-reducing properties.

Example 3

(80) Into a 1 L four-necked flask equipped with a stirring machine and a condenser tube, 38.4 g (0.24 mol) of 3-(1-piperazinyl)-1,2-propanediol, 25.8 g (0.08 mol) of octadecyl bromide, isopropanol (250 g) and 8.65 g (0.08 mol) of sodium carbonate were added, followed by heating at 90 C. for 8 hours in a stream of nitrogen. After completion of heating, sodium carbonate was removed by filtration, and 2-propanol was removed by vacuum distillation. Then, only the oil layer was collected by extraction with chloroform, which was subjected to vacuum distillation and vacuum drying to obtain 30.8 g (yield: 95.9%) of white crystalline 3-(4-octadecyl-1-piperazinyl)-1,2-propanediol.

(81) Identification was conducted from the results of .sup.1H-NMR measurement, .sup.13C-NMR measurement and elemental analysis.

(82) .sup.1H-NMR (CDCl.sub.3): 3.71-3.90 (m, 2H), 3.49-3.55 (dd, 1H), 2.43-2.84 (m, 12H), 1.55 (s, 2H), 1.19-1.25 (m, 30H), 0.86-0.90 (t, 3H) [ppm].

(83) .sup.13C-NMR (CDCl.sub.3): 67.36, 65.07, 60.54, 58.67, 52.96, 32.17, 29.95, 29.91, 29.85, 29.82, 29.74, 29.61, 27.68, 26.53, 22.94, 14.37 [ppm].

(84) Elemental analysis (calculated value): C=72.8, H=12.7, N=6.8,

(85) Elemental analysis (calculated value): C=73.0, H=13.0, N=6.8.

(86) Then, into a 100 mL round bottom flask, 4.13 g of 3-(4-octadecyl-1-piperazinyl)-1,2-propanediol and 10 g of toluene were added, followed by heating at 80 C. for dissolution, and an aqueous molybdenum dispersion having 1.51 g of molybdenum trioxide dispersed in 10 g of water was dropwise added. On that occasion, the Mo atom/amine (molar ratio) was 1.05. Then, the reaction mixture was aged at 80 C. for 2 hours and at 110 C. for 1 hour. After completion, unreacted molybdenum trioxide was removed by filtration, and the solvent was removed by vacuum distillation and vacuum drying to obtain 4.74 g of deep green solid friction-reducing agent (A-3). The molybdenum content in the friction-reducing agent (A-3) was 8.2 wt %.

(87) Using the obtained friction-reducing agent (A-3), oil solubility and friction properties were evaluated, and the results are shown in Table 1. The friction-reducing agent (A-3) was excellent in oil solubility, had a low coefficient of friction and had favorable friction-reducing properties.

Example 4

(88) Into a 100 mL round bottom flask, 3.29 g of 3-(4-dodecyl-1-piperazinyl)-1,2-propanediol prepared in Example 1 and 10 g of toluene were added, followed by heating at 80 C. for dissolution, and an aqueous molybdenum dispersion having 2.15 g of molybdenum trioxide dispersed in 10 g of water was dropwise added. On that occasion, the Mo atom/amine (molar ratio) was 1.5. Then, the reaction mixture was aged at 80 C. for 2 hours and at 110 C. for 1 hour. After completion, unreacted molybdenum trioxide was removed by filtration, and the solvent was removed by vacuum distillation and vacuum drying to obtain 4.12 g of liver brown solid friction-reducing agent (A-4). The molybdenum content in the friction-reducing agent (A-4) was 21.7 wt %.

(89) Using the obtained friction-reducing agent (A-4), oil solubility and friction properties were evaluated, and the results are shown in Table 1. The friction-reducing agent (A-4) was excellent in oil solubility, had a low coefficient of friction and had favorable friction-reducing properties.

Example 5

(90) Into a 1 L four-necked flask equipped with a stirring machine and a condenser tube, 38.4 g (0.24 mol) of 3-(1-piperazinyl)-1,2-propanediol, 15.4 g (0.08 mol) of 2-ethylhexyl bromide, isopropanol (250 g) and 8.65 g (0.08 mol) of sodium carbonate were added, followed by heating at 90 C. for 8 hours in a stream of nitrogen. After completion of heating, sodium carbonate was removed by filtration, and 2-propanol was removed by vacuum distillation. Then, only the oil layer was collected by extraction with chloroform, which was subjected to vacuum distillation and vacuum drying to obtain 20.1 g (yield: 92.2%) of white crystalline 3-(4-(2-ethylhexyl)-1-piperazinyl)-1,2-propanediol.

(91) Identification was conducted from the results of .sup.1H-NMR measurement, .sup.13C-NMR measurement and elemental analysis.

(92) .sup.1H-NMR (CDCl.sub.3): 3.69-3.86 (m, 2H), 3.49-3.55 (dd, 1H), 2.14-2.70 (m, 12H), 1.26-1.46 (m, 9H), 0.82-0.89 (m, 6H) [ppm].

(93) .sup.13C-NMR (CDCl.sub.3): 67.18, 65.32, 63.07, 60.78, 53.66, 36.30, 31.62, 29.13, 24.81, 23.35, 14.38, 10.95 [ppm].

(94) Elemental analysis (calculated value): C=66.1, H=11.8, N=10.3,

(95) Elemental analysis (measured value): C=66.2, H=12.0, N=10.4.

(96) Then, into a 100 mL round bottom flask, 3.54 g of 3-(4-(2-ethylhexyl)-1-piperazinyl)-1,2-propanediol and 10 g of toluene were added, followed by heating at 80 C. for dissolution, and an aqueous molybdenum dispersion having 1.97 g of molybdenum trioxide dispersed in 10 g of water was dropwise added. On that occasion, the Mo atom/amine (molar ratio) was 1.05. Then, the reaction mixture was aged at 80 C. for 2 hours and at 110 C. for 1 hour. After completion, unreacted molybdenum trioxide was removed by filtration, and the solvent was removed by vacuum distillation and vacuum drying to obtain 3.39 g of deep green solid friction-reducing agent (A-5). The molybdenum content in the friction-reducing agent (A-5) was 16.3 wt %.

(97) Using the obtained friction-reducing agent (A-5), oil solubility and friction properties were evaluated, and the results are shown in Table 2. The friction-reducing agent (A-5) was excellent in oil solubility, had a low coefficient of friction and had favorable friction-reducing properties.

Example 6

(98) Into a 1 L four-necked flask equipped with a stirring machine and a condenser tube, 31.2 g (0.24 mol) of 1-piperazineethanol, 19.3 g (0.08 mol) of dodecyl bromide, isopropanol (250 g) and 8.65 g (0.08 mol) of sodium carbonate were added, followed by heating at 90 C. for 8 hours in a stream of nitrogen. After completion of heating, sodium carbonate was removed by filtration, and 2-propanol was removed by vacuum distillation. Then, only the oil layer was collected by extraction with chloroform, which was subjected to vacuum distillation and vacuum drying to obtain 23.55 g (yield: 94.2%) of white crystalline 4-dodecyl-1-piperazineethanol.

(99) Identification was conducted from the results of .sup.1H-NMR measurement, .sup.13C-NMR measurement and elemental analysis.

(100) .sup.1H-NMR (CDCl.sub.3): 3.67-3.70 (t, 2H), 2.80 (m, 8H), 2.65-2.68 (t, 2H), 2.51-2.56 (t, 2H), 1.61 (s, 2H), 1.19-1.26 (m, 18H), 0.86-0.90 (t, 3H) [ppm].

(101) .sup.13C-NMR (CDCl.sub.3): 59.52, 58.43, 57.88, 52.54, 52.12, 32.09, 29.81, 29.75, 29.60, 29.56, 29.52, 27.52, 26.08, 22.86, 14.32 [ppm].

(102) Elemental analysis (calculated value): C=72.4, H=12.8, N=9.4,

(103) Elemental analysis (measured value): C=72.4, H=12.9, N=9.4.

(104) Then, into a 100 mL round bottom flask, 4.48 g of 4-dodecyl-1-piperazineethanol and 15 g of toluene were added, followed by heating at 80 C. for dissolution, and an aqueous molybdenum dispersion having 2.16 g of molybdenum trioxide dispersed in 15 g of water was dropwise added. On that occasion, the Mo atom/amine (molar ratio) was 1.05. Then, the reaction mixture was aged at 80 C. for 2 hours and at 110 C. for 1 hour. After completion, unreacted molybdenum trioxide was removed by filtration, and the solvent was removed by vacuum distillation and vacuum drying to obtain 4.34 g of deep green solid friction-reducing agent (A-6). The molybdenum content in the friction-reducing agent (A-6) was 6.4 wt %.

(105) Using the obtained friction-reducing agent (A-6), oil solubility and friction properties were evaluated, and the results are shown in Table 2. The friction-reducing agent (A-6) was excellent in oil solubility, had a low coefficient of friction and had favorable friction-reducing properties.

Example 7

(106) Into a 1 L four-necked flask equipped with a stirring machine and a condenser tube, 19.0 g (0.12 mol) of 3-(1-piperazinyl)-1,2-propanediol, 16.7 g (0.04 mol) of 1-bromo-2-decyl-tetradecane, isopropanol (200 g) and 4.45 g (0.042 mol) of sodium carbonate were added, followed by heating at 90 C. for 8 hours in a stream of nitrogen. After completion of heating, sodium carbonate was removed by filtration, and 2-propanol was removed by vacuum distillation. Then, only the oil layer was collected by extraction with chloroform, which was subjected to vacuum distillation and vacuum drying to obtain 18.9 g (yield: 95.1%) of pale yellow oil 3-(4-(2-decyltetradecyl)-1-piperazinyl)-1,2-propanediol.

(107) Identification was conducted from the results of .sup.1H-NMR measurement, .sup.13C-NMR measurement and elemental analysis.

(108) .sup.1H-NMR (CDCl.sub.3): 3.68-3.84 (m, 2H), 3.48-3.53 (dd, 1H), 2.11-2.65 (m, 12H), 1.48 (s, 1H), 1.19-1.26 (m, 40H), 0.86-0.90 (t, 6H) [ppm].

(109) .sup.13C-NMR (CDCl.sub.3): 67.19, 65.34, 63.63, 60.81, 53.90, 35.04, 32.60, 32.18, 30.36, 29.96, 29.92, 29.62, 26.84, 22.94, 14.37 [ppm].

(110) Elemental analysis (calculated value): C=74.9, H=13.0, N=5.6,

(111) Elemental analysis (measured value): C=75.0, H=13.4, N=5.7.

(112) Then, into a 100 mL round bottom flask, 4.97 g of 3-(4-(2-decyltetradecyl)-1-piperazinyl)-1,2-propanediol and 12 g of toluene were added, followed by heating at 80 C. for dissolution, and an aqueous molybdenum dispersion having 1.44 g of molybdenum trioxide dispersed in 12 g of water was dropwise added. On that occasion, the Mo atom/amine (molar ratio) was 1.05. Then, the reaction mixture was aged at 80 C. for 2 hours and at 110 C. for 1 hour. After completion, unreacted molybdenum trioxide was removed by filtration, and the solvent was removed by vacuum distillation and vacuum drying to obtain 6.23 g of a deep green solid friction-reducing agent (A-7). The molybdenum content in the friction-reducing agent (A-7) was 12.7 wt %.

(113) Using the obtained friction-reducing agent (A-7), oil solubility and friction properties were evaluated, and the results are shown in Table 2. The friction-reducing agent (A-7) was excellent in oil solubility, had a low coefficient of friction and had favorable friction-reducing properties.

Example 8

(114) Into a 100 mL round bottom flask, 4.97 g of 3-(4-(2-decyltetradecyl)-1-piperazinyl)-1,2-propanediol prepared in Example 7 and 12 g of toluene were added, followed by heating at 80 C. for dissolution, and an aqueous molybdenum dispersion having 0.96 g of molybdenum trioxide dispersed in 12 g of water was dropwise added. On that occasion, the Mo atom/amine (molar ratio) was 0.75. Then, the reaction mixture was aged at 80 C. for 2 hours and at 110 C. for 1 hour. After completion, unreacted molybdenum trioxide was removed by filtration, and the solvent was removed by vacuum distillation and vacuum drying to obtain 5.45 g of a deep green solid friction-reducing agent (A-8). The molybdenum content in the friction-reducing agent (A-8) was 8.8 wt %.

(115) Using the obtained friction-reducing agent (A-8), oil solubility and friction properties were evaluated, and the results are shown in Table 2. The friction-reducing agent (A-8) was excellent in oil solubility, had a low coefficient of friction and had favorable friction-reducing properties.

Example 9

(116) Into a 1 L four-necked flask equipped with a stirring machine and a condenser tube, 70.9 g (0.20 mol) of 2-decyl-1-tetradecanol, 22.3 g (0.22 mol) of triethylamine and 1,320 g of dichloromethane were added, 25.2 g (0.22 mol) of methanesulfonyl chloride was dropwise added in a stream of nitrogen in a state cooled to 10 C. to 0 C., and the reaction mixture was aged at from 10 to 0 C. for 30 minutes and at 25 C. for 17 hours. Then, extraction with a saturated salt solution and removal of the solvent were carried out to obtain 93.0 g of an intermediate.

(117) Then, into a 1 L four-necked flask equipped with a stirring machine and a condenser tube, 92.6 g of the intermediate, 124.4 g (0.54 mol) of 3-(1-piperazinyl)-1,2-propanediol and 150 g of ethanol were added, followed by reaction at 150 C. for 13 hours in a stream of nitrogen. Then, only the oil layer was collected by extraction with chloroform, which was subjected to vacuum distillation and vacuum drying to obtain 81.8 g (yield: 94.0%) of pale yellow oil 3-(4-(2-decyltetradecyl)-1-piperazinyl)-1,2-propanediol.

(118) Identification was conducted from the results of .sup.1H-NMR measurement, .sup.13C-NMR measurement and elemental analysis.

(119) .sup.1H-NMR (CDCl.sub.3): 3.71-3.82 (m, 2H), 3.50-3.53 (dd, 1H), 2.12-2.66 (m, 12H), 1.48 (s, 1H), 1.20-1.26 (m, 40H), 0.86-0.90 (t, 6H) [ppm].

(120) 13C-NMR (CDCl.sub.3): 66.76, 65.04, 63.40, 60.37, 53.71, 34.82, 32.37, 31.94, 30.11, 29.72, 29.69, 29.38, 26.61, 22.70, 14.13 [ppm].

(121) Elemental analysis (calculated value): C=74.9, H=13.0, N=5.6,

(122) Elemental analysis (measured value): C=75.0, H=13.1, N=5.7.

(123) Then, into a 100 mL round bottom flask, 9.94 g of 3-(4-(2-decyltetradecyl)-1-piperazinyl)-1,2-propanediol and 25 g of toluene were added, followed by heating at 80 C. for dissolution, and an aqueous molybdenum dispersion having 3.02 g of molybdenum trioxide dispersed in 25 g of water was dropwise added. On that occasion, the Mo atom/amine (molar ratio) was 1.05. Then, the reaction mixture was aged at 110 C. for 1 hour. After completion, unreacted molybdenum trioxide was removed by filtration, and the solvent was removed by vacuum distillation and vacuum drying to obtain 11.5 g of a deep green solid friction-reducing agent (A-9). The molybdenum content in the friction-reducing agent (A-9) was 14.0 wt %.

(124) The friction-reducing agent (A-9) was blended with base oil (C-1) so that the molybdenum concentration would be 500 ppm, and tris(dimethylamino)borane as a boron compound was blended at a concentration of 0.1 wt %, and further, zinc dialkyldithiophosphate (ZnDTP, manufactured by ADEKA CORPORATION, KIKU-LUBE Z-112) as an abrasion inhibitor was blended so that the zinc concentration would be 1,000 ppm, to prepare a blended oil. Using the obtained blended oil, oil solubility and low temperature friction properties were evaluated. The results are shown in Table 3.

(125) The obtained blended oil was excellent in oil solubility, had a low coefficient of friction and had favorable low temperature friction properties.

(126) TABLE-US-00003 TABLE 3 Example 9 Example 10 Example 11 Friction-reducing agent A-9 A-9 A-9 Amine Name 3-(4-(2-decyltetradecyl)- 3-(4-(2-decyltetradecyl)- 3-(4-(2-decyltetradecyl)- 1-piperazinyl)-1,2- 1-piperazinyl)-1,2- 1-piperazinyl)-1,2- propanediol propanediol propanediol Structural formula Molybdenum MoO.sub.3 MoO.sub.3 MoO.sub.3 Mo/amine (molar ratio) 1.05 1.05 1.05 Mo content (wt %) 14.0 14.0 14.0 Boron Name Tris(dimethylamino) Tris(dimethylamino) Tris(dimethylamino) compound borane borane borane Amount 0.10 0.50 1.0 blended [wt %] Oil solubility Results Soluble Soluble Soluble Evaluation A A A Low temperature Coefficient 0.070 0.071 0.070 Friction of friction properties Evaluation A A A

Example 10

(127) A blended oil was prepared in the same manner as in Example 9 except that the amount of tris(dimethylamino)borane as a boron compound blended was 0.5 wt %, and oil solubility and low temperature friction properties were evaluated. The results are shown in Table 3.

(128) The obtained blended oil was excellent in oil solubility, had a low coefficient of friction and had favorable low temperature friction properties.

Example 11

(129) A blended oil was prepared in the same manner as in Example 9 except that the amount of tris(dimethylamino)borane as a boron compound blended was 1.0 wt %, and oil solubility and low temperature friction properties were evaluated. The results are shown in Table 3.

(130) The obtained blended oil was excellent in oil solubility, had a low coefficient of friction and had favorable low temperature friction properties.

Comparative Example 1

(131) Using friction-reducing agent (B-1) comprising base oil (C-1) and zinc dialkyldithiophosphate (ZnDTP, manufactured by ADEKA CORPORATION, KIKU-LUBE Z-112) as an abrasion inhibitor blended so that the zinc concentration would be 1,000 ppm, oil solubility and friction properties were evaluated, and the results are shown in Table 4. The friction-reducing agent (B-1) had a high coefficient of friction and was inferior in friction-reducing properties.

(132) TABLE-US-00004 TABLE 4 Comparative Comparative Comparative Comparative Example 1 Example 2 Example 3 Example 4 Friction-reducing agent B-1 B-2 B-3 B-4 Amine Name 3-(1-piperazinyl)- 2,2,-(dodecylimino) Molybdenum 1,2-propanediol bisethanol oxysulfide dithiocarbamate Structural formula Molybdenum MoO.sub.3 Mo/amine (molar ratio) 1.05 Mo content (wt %) 19.3 10.0 Oil solubility Results Soluble Separated Suspended Soluble Evaluation A C B A Friction Coefficient 0.156 Evaluation 0.131 0.101 properties of friction impossible Evaluation C C C C

Comparative Example 2

(133) Using friction-reducing agent (B-2) comprising base oil (C-1) and 3-(1-piperazinyl)-1,2-propanediol blended at a concentration of 0.1 wt %, oil solubility and friction properties were evaluated, and the results are shown in Table 4. The friction-reducing agent (B-2) was inferior in oil solubility and was separated from the base oil, and the friction properties could not be evaluated.

Comparative Example 3

(134) Into a 100 mL round bottom flask, 3.42 g of 2,2-(dodecylimino)bis-ethanol and 15 g of toluene were added, followed by heating at 80 C. for dissolution, and an aqueous molybdenum dispersion having 1.89 g of molybdenum trioxide dispersed in 15 g of water was dropwise added. On that occasion, the Mo atom/amine (molar ratio) was 1.05. Then, the reaction mixture was aged at 80 C. for 2 hours and at 110 C. for 1 hour. After completion, unreacted molybdenum trioxide was removed by filtration, and the solvent was removed by vacuum distillation and vacuum drying to obtain 3.63 g of deep green solid friction-reducing agent (B-3). The molybdenum content in the friction-reducing agent (B-3) was 19.3 wt %.

(135) Using the obtained friction-reducing agent (B-3), oil solubility and friction properties were evaluated, and the results are shown in Table 4. The friction-reducing agent (B-3) was suspended in the base oil, had a high coefficient of friction and was inferior in friction-reducing properties.

Comparative Example 4

(136) Using friction-reducing agent (B-4) comprising base oil (C-1) and molybdenum oxysulfide dithiocarbamate (MoDTC, manufactured by ADEKA CORPORATION, SAKURA-LUBE 525, Mo content: 10.0 wt %) blended so that the molybdenum concentration would be 500 ppm, oil solubility and friction properties were evaluated, and the results are shown in Table 4. The friction-reducing agent (B-4) had a high coefficient of friction and was inferior in friction-reducing properties.

(137) The present invention was described in detail with reference to specific embodiments, however, it is obvious for the person skilled in the art that various changes and modifications are possible without departing from the intention and the scope of the present invention.

INDUSTRIAL APPLICABILITY

(138) The friction-reducing agent of the present invention is excellent in friction-reducing properties and is thereby suitable as an additive for a lubricating oil. It is particularly useful as an additive for a gasoline engine oil, a Diesel engine oil, a jet engine oil and a gear oil.