JP2006282797A - Lubricant and lubricating fluid composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a lubricant having excellent friction-reducing effect, and to provide a lubricating fluid composition containing the same, particularly such one suitable to applications for which energy saving is required including motor vehicles and industrial machinery and equipment. <P>SOLUTION: The lubricant comprises a hydroxy group-containing amine compound of the formula:R<SP>1</SP>-N(R<SP>2</SP>)-R<SP>3</SP>-(OH)<SB>n</SB>( wherein, R<SP>1</SP>is a 6-30C alkyl or alkenyl; R<SP>2</SP>is H or the like; R<SP>3</SP>is a residue resulted from removing hydroxy group(s) from a 1-10C monohydric or polyhydric alcohol; and n is an integer of 1-10 ). The lubricating fluid composition comprises the lubricant and a lubricating fluid base consisting of one or more materials selected from water, alcohol, carboxylic acid, mineral oil, synthetic oil and fat-and-oil. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a lubricant and a lubricating fluid composition, and more particularly to a novel lubricant and a lubricating fluid composition that are excellent in a friction reducing effect.

In recent years, reduction of carbon dioxide emissions has become an urgent issue, and further energy saving is required for automobiles and industrial machinery. In addition to energy savings, the lubricating fluids used for these include metals, phosphorus, sulfur, etc. in addition to low friction performance and longer life, from the viewpoint of mitigating the impact on automobile exhaust gas aftertreatment devices and waste oil treatment. There is a demand for reduction.
In order to enhance the low friction performance, a sulfur-containing molybdenum compound such as molybdenum dithiocarbamate or molybdenum dithiophosphate is generally used as a lubricant, which is effective (for example, Patent Document 1).
However, these molybdenum compounds still contain problems such as effects on automobile exhaust gas aftertreatment devices and waste oil treatment such as containing sulfur as well as metals and sulfur. In addition, it is difficult to say that the use of any or all of metal, sulfur and phosphorus is preferable depending on the type of mechanical device, the sliding material used, the usage environment, and the like.
JP-A-8-302378

SUMMARY OF THE INVENTION An object of the present invention is to provide a novel lubricant excellent in friction reducing effect suitable for a mechanical device particularly requiring a friction reducing effect, and a lubricating fluid composition containing the same.
Another object of the present invention is to provide a novel lubricant that is excellent in friction reduction effect and can reduce the influence on the exhaust gas aftertreatment device, the problem of waste oil treatment, and the like, and a lubricating fluid composition including the same.

That is, according to the present invention, a lubricant comprising a hydroxy group-containing amine compound represented by the formula (1) is provided.
R ¹ —N (R ² ) —R ³ — (OH) n (1)
(In Formula (1), R ¹ is an alkyl group or alkenyl group having 6 to 30 carbon atoms, R ² is hydrogen, an alkyl group or alkenyl group having 1 to 30 carbon atoms, —R ⁴ — (OH) m, or — ^{(R 5 O) t-H} ( wherein, residue R ⁴ is other than a hydroxy group from monohydric or polyhydric alcohols having 1 to 10 carbon atoms, R ⁵ is an alkylene group having 1 to 4 carbon atoms, m or t independently represents an integer of 1 to 10), R ³ represents a residue obtained by removing a hydroxy group from a monovalent or polyhydric alcohol having 1 to 10 carbon atoms, and n represents an integer of 1 to 10).
Moreover, according to this invention, the lubricating fluid base material which consists of 1 type, or 2 or more types chosen from water, alcohol, carboxylic acid, mineral oil, synthetic oil, and fats and oils and the lubricant which consists of the said hydroxyl group containing amine compound are contained. A lubricating fluid composition is provided.

The lubricant according to the present invention is composed of a hydroxyl group-containing amine compound represented by the above formula (1), and does not contain sulfur and / or phosphorus like a lubricant such as sulfur and / or phosphorus-containing molybdenum compound. The friction reduction effect of the lubricating fluid can be improved while reducing the influence on the aftertreatment device and the problem of waste oil treatment.
Since the lubricating fluid composition of the present invention contains the above-described lubricant of the present invention, it can contribute to energy saving of mechanical devices requiring low friction performance, such as automobiles and industrial mechanical devices.

Hereinafter, the present invention will be described in detail.
The lubricant of the present invention comprises a hydroxy group-containing amine compound represented by the above formula (1), and can be used as a lubricating component for improving the friction reducing effect of various lubricating fluids.
In the formula (1), R ¹ is an alkyl group or alkenyl group having 6 to 30 carbon atoms, and is preferably an alkyl group or alkenyl group having 8 or more carbon atoms, more preferably 12 or more carbon atoms in terms of oil solubility. An alkyl group or an alkenyl group. From the viewpoint of availability of raw materials, an alkyl group or alkenyl group having preferably 24 or less carbon atoms, more preferably 20 or less carbon atoms is preferred.

In Formula (1), R ² is hydrogen, an alkyl or alkenyl group having 1 to 30 carbon atoms, —R ⁴ — (OH) m, or — (R ⁵ O) t—H, preferably hydrogen, carbon An alkyl group or an alkenyl group of Formula 1 to 18 and —R ⁴ — (OH) m, more preferably hydrogen or —R ⁴ — (OH) m, and particularly preferably hydrogen. Moreover, as an alkyl group or alkenyl group in R < ² >, a C1-C6 alkyl group or alkenyl group is also mentioned preferably.
Here, R ⁴ is the same group as R ³ described later, and the same examples can be given as preferable groups. R ⁵ is an alkylene group having 1 to 4 carbon atoms, preferably an alkylene group having 2 or 3 carbon atoms. m represents an integer of 1 to 10, preferably 1 to 6, particularly preferably 1 to 4. m or 1 to 10, preferably 1 to 6, more preferably an integer of 1 to 3, and particularly preferably 2. t shows the integer of 1-10.

In formula (1), R ³ is a residue obtained by removing a hydroxy group from a 1-10 valent alcohol having 1 to 10 carbon atoms, preferably a residue obtained by removing a hydroxy group from a 1-6 valent alcohol having 2 to 6 carbon atoms. More preferably, it is a residue obtained by removing a hydroxy group from a 1-3 carbon alcohol having 3 carbon atoms, and particularly preferably a residue obtained by removing a hydroxy group from a divalent alcohol having 3 carbon atoms. N is an integer of 1 to 10, preferably 1 to 6, more preferably 1 to 3, particularly preferably 2.

Preferred examples of the hydroxy group-containing amine compound represented by the formula (1) include compounds satisfying the following (a) to (d).
(a) R ¹ is an alkyl group or alkenyl group having 6 to 30 carbon atoms, R ² is hydrogen, R ³ is a residue obtained by removing a hydroxy group from a monovalent or divalent alcohol having 3 carbon atoms, n is 1 Or a compound which is 2, (b) R ¹ is an alkyl group or alkenyl group having 6 to 30 carbon atoms, R ² is —R ⁴ — (OH) m, R ³ and R ⁴ are each independently 3 carbon atoms. A residue obtained by removing a hydroxy group from a monohydric or dihydric alcohol, a compound in which n and m are each independently 1 or 2, (c) R ¹ is an alkyl group or an alkenyl group having 6 to 30 carbon atoms, R ² is — (R ⁵ O) t—H, R ⁵ is an alkylene group having 2 or 3 carbon atoms, t is an integer of 1 to 4, and R ³ is a monovalent or divalent alcohol having 3 carbon atoms. except residues, compounds wherein n is 1 or 2, (d) R ¹ is an alkyl or alkenyl group having 6 to 30 carbon atoms, R ² is 1 to 3 carbon atoms Alkyl or alkenyl group, residue R ³ is other than a hydroxy group from a mono- or dihydric alcohol having 3 carbon atoms, n can be mentioned compounds wherein one or two. Especially, it is preferable that it is 1 type, or 2 or more types chosen from (a)-(c), It is more preferable that it is (a) and / or (b), It is especially preferable that it is (a).
A specific example of (a) is preferably C ₁₈ H ₃₅ —NH—CH ₂ CH ₂ (OH) CH ₂ (OH).
A specific example of (b) is preferably C ₁₈ H ₃₅ —N [CH ₂ CH ₂ (OH) CH ₂ (OH)] ₂ .
Specific examples of _{(c), C 18 H 35} -N [(CH 2 CH 2 O) (1-4) H] -CH 2 CH 2 (OH) CH 2 (OH) may be preferably mentioned.
A specific example of (d) is preferably [C ₁₈ H ₃₅ —] ₂ N—CH ₂ CH ₂ (OH) CH ₂ (OH).

  The method for producing the hydroxy group-containing amine compound represented by the formula (1) is not limited at all. For example, an amine compound selected from primary alkyl or alkenyl amine and its alkylene oxide adduct, secondary alkyl or alkenyl amine and A method of reacting with glycidol can be exemplified. These methods are disclosed in, for example, JP-A-58-63736, JP-A-46-21306, and US Pat. No. 2,784,233.

  In the present invention, for example, as a method for producing a compound satisfying the above (a), specifically, a methanol solution containing the same mole of glycidol is dropped into a primary alkyl or alkenylamine dissolved in a solvent such as toluene. Examples of the method include mixing and reacting at 30 to 100 ° C., preferably 60 to 90 ° C., and distilling off the remaining toluene and methanol by distillation under reduced pressure.

  The lubricating fluid composition of the present invention comprises a lubricating fluid base material composed of one or more selected from water, alcohol, carboxylic acid, mineral oil, synthetic oil, and oil and fat, and a hydroxy group represented by the formula (1) And a lubricant of the present invention comprising an amine compound, and if necessary, for example, a phosphorus-containing compound, a metal-based detergent, an ashless dispersant, an antioxidant, a friction modifier, a viscosity index improver, an antiwear agent, You may contain at least 1 sort (s) chosen from a fluid improvement agent, a demulsifier, a metal deactivator, an antifoamer, a corrosion inhibitor, and a rust inhibitor.

Examples of the alcohol include monovalent or polyhydric alcohols.
Examples of the monohydric alcohol include saturated or unsaturated aliphatic alcohols having 1 to 30 carbon atoms, preferably 6 to 24 carbon atoms, and these may be linear or branched. Specifically, for example, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, icosanol, hexenol, heptenol , Monovalent saturated or unsaturated aliphatic alcohols such as octenol, nonenol, decenol, undecenol, dodecenol, tridecenol, tetradecenol, pentadecenol, hexadecenol, heptadecenol, octadecenol, etc., which may be linear or branched. The position of the double bond is also arbitrary.
Examples of the polyhydric alcohol include those having 2 to 10 valences, preferably 2 to 6 valences. Specific examples include polyethylene glycols such as ethylene glycol, diethylene glycol, and ethylene glycol 3 to 15 mers, propylene. Polypropylene glycol such as glycol, dipropylene glycol, 3-15 mer of propylene glycol, 1,3-propanediol, 1,2-propanediol, 2-methyl-1,2-propanediol, 2-methyl-1, 3-Propanediol, neopentyl glycol, glycerin, diglycerin, triglycerin, trimethylol ethane, trimethylol propane, trimethylol butane and the like trimethylol alkanes and their 2-tetramers, pentaerythritol, dipentaerythritol, 1 2,4-butanetriol, 1,3,5-pentanetriol, 1,2,6-hexanetriol, 1,2,3,4-butanetetrol, sorbitol, sorbitan, sorbitol glycerin condensate, adonitol, arabitol, Examples thereof include divalent to hexavalent polyhydric alcohols such as xylitol and mannitol, and mixtures thereof. Among these, since higher oxidative stability is obtained, ethylene glycol, propylene glycol, neopentyl glycol, glycerin, diglycerin, triglycerin, trimethylolethane, trimethylolpropane, pentaerythritol, sorbitan, and mixtures thereof, etc. Is preferred.

  The carboxylic acid may be a monobasic acid or a polybasic acid, and its carbon number is arbitrary, but a saturated or unsaturated fatty acid having 6 to 30 carbon atoms, particularly 8 to 24 carbon atoms is preferable. Examples of the saturated or unsaturated fatty acid having 6 to 30 carbon atoms include hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, and heptadecane. Acid, octadecanoic acid, nonadecanoic acid, icosanoic acid, hexenoic acid, heptenoic acid, octenoic acid, nonenoic acid, decenoic acid, undecenoic acid, dodecenoic acid, tridecenoic acid, tetradecenoic acid, pentadecenoic acid, hexadecenoic acid, heptadecenoic acid, octadecenoic acid, etc. These may be linear or branched, and the position of the double bond is arbitrary. Of these, saturated or unsaturated fatty acids having 12 to 18 carbon atoms such as lauric acid, stearic acid, and oleic acid are particularly preferable.

The mineral oil is not particularly limited, and specifically, a light mineral oil obtained by subjecting a fraction obtained by atmospheric distillation of crude oil to purification, reforming or the like by a known method, or atmospheric distillation of crude oil. The lubricating oil fraction obtained by distilling the atmospheric residue obtained in this way under reduced pressure is subjected to one or more treatments such as solvent removal, solvent extraction, hydrocracking, solvent dewaxing, and hydrorefining. Or a base oil produced by a method of isomerizing a wax isomerized mineral oil, GTL WAX (Gas Liquid Wax), or the like.
Specific examples of the synthetic oil include polybutene or hydrides thereof; poly-α-olefins such as 1-octene oligomers and 1-decene oligomers or hydrides thereof; ditridecyl glutarate, di-2-ethylhexyl adipate, Diesters such as diisodecyl adipate, ditridecyl adipate, di-2-ethylhexyl sebacate; polyol esters such as dialkylpropane diol having 5 to 19 carbon atoms such as neopentyl glycol and 2-butyl-2-ethylpropane-1,3 diol A trimethylol alkane having 5 to 15 carbon atoms such as 1,1,1-trimethylolethane, 1,1,1-trimethylolpropane, 1,1,1-trimethylolbutane; pentaerythritol, dipentaerythritol, etc. At least selected from polyols 1 type and valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, oleic acid, isopentanoic acid, 2-methylhexanoic acid, 2-ethylpentanoic acid, 2-ethylhexanoic acid, 3, 5, 5 -Monoester, diester, triester, tetraester and mixtures thereof consisting of at least one selected from fatty acids such as trimethylhexanoic acid; aromatic synthetic oils such as alkylnaphthalene, alkylbenzene, aromatic ester; these two The above mixture can be illustrated.
Examples of the fats and oils include natural fats and oils such as animal oils and vegetable oils, and fats and oils obtained by purifying these.
As the lubricating fluid base material, water, the alcohol, the carboxylic acid, the mineral oil, the synthetic oil, the oil or fat, or an arbitrary mixture of two or more selected from these can be used. Examples thereof include one or more mineral oils, one or more synthetic oils, a mixed oil of one or more mineral oils and one or more synthetic oils, and the like. In the following, one or more of these selected from the group consisting of mineral oil, synthetic oil and fat may be referred to as a lubricating fluid base oil.

The kinematic viscosity of the lubricating base oil is not particularly limited, but the kinematic viscosity at 40 ° C. is usually 1 to 500 mm ² / s, preferably ² to 100 mm ² / s. The kinematic viscosity at 100 ° C. of the lubricating fluid base oil when the lubricating fluid composition of the present invention is used under high temperature conditions is preferably 1 to 100 mm ² / s, more preferably ^{2 to 20} mm ² / s. preferably 2.5~8mm ² / s, more preferably from 3 to 5 mm ² / s. By setting the kinematic viscosity at 100 ° C. to 1 mm ² / s or more, excellent lubricity can be obtained by retaining the oil film, and by reducing the viscosity, particularly 5 mm ² / s or less, energy saving can be further improved by reducing stirring resistance. it can.

  The viscosity index of the lubricating base oil is not particularly limited and is arbitrary, but is preferably 80 or more, more preferably 100 or more, and particularly preferably 120 or more so that excellent viscosity characteristics from low temperature to high temperature can be obtained. . The upper limit of the viscosity index is not particularly limited. For example, the upper limit of the viscosity index when using normal paraffin, slack wax, GTL WAX or the like, or isoparaffin mineral oil obtained by isomerizing these is about 135 to 180, and complex ester The upper limit of the viscosity index when using a base oil or an HVI-PAO base oil is about 150 to 250.

  The aromatic content of the lubricating fluid base oil is not particularly limited, but is usually 50% by mass or less, more preferably 15% by mass or less, further preferably 5% by mass or less, and particularly preferably 3% by mass or less. It may be mass%. Here, the aromatic content means the total aromatic content measured according to ASTM D2549. The sulfur content of the lubricating fluid base material is not particularly limited, but is preferably 0.3% by mass or less, more preferably 0.05% by mass or less, and particularly preferably 0.005% by mass or less. Further, the evaporation loss amount of the lubricating base oil is preferably 40% by mass or less, more preferably 20% by mass or less, and further preferably 16% by mass or less in terms of NOACK evaporation. By making the NOACK evaporation amount 40% by mass or less, it becomes easy to suppress the evaporation loss. Here, the NOACK evaporation amount is measured in accordance with ASTM D5800.

Examples of phosphorus-containing compounds that can be contained in the lubricating fluid composition of the present invention include generally known phosphorus compounds, such as zinc dialkyldithiophosphates, zinc dialkylphosphates, (sub) phosphate esters, thio (sub) Phosphorus esters and phosphorus-containing compounds such as amine salts thereof can be mentioned. Among these, primary or secondary zinc dialkyldithiophosphates, primary or secondary zinc dialkyldiphosphates, phosphate triesters, and the like are preferable. These usually have a hydrocarbon group having 3 to 30 carbon atoms.
The content in the case of containing the phosphorus-containing compound is not particularly limited, but is preferably 0.005 to 0.4% by mass, more preferably 0.01 to 0.1% as the phosphorus content based on the total amount of the composition. It is preferably 0.02 to 0.08% by mass, more preferably 0.03 to 0.06% by mass. By containing 0.005% by mass or more of a phosphorus-containing compound, the anti-wear property is further improved, and in particular, by reducing the phosphorus-containing compound to 0.1% by mass or less, a composition having a more excellent friction reducing effect is obtained. Can do.

Examples of metal detergents that can be contained in the lubricating fluid composition of the present invention include generally known metal detergents such as alkaline earth metal sulfonates, alkaline earth metal finates, and alkaline earth metal salicylates. A metallic detergent is mentioned. These may be neutral or (over) basic, and those having a basic number of 0 to 500 mgKOH / g are generally available.
Although content in the case of containing a metallic detergent is not particularly limited, it is usually 0.005 to 5% by mass as a metal amount based on the total amount of the composition.
Examples of the ashless dispersant that can be contained in the lubricating fluid composition of the present invention include generally known ashless dispersants, such as succinimide-based benzylamine-based having an alkyl group or alkenyl group having 40 to 400 carbon atoms. And amine compounds and boron compound derivatives, phosphorus compound derivatives, and acylated derivatives thereof.
Although content in the case of containing an ashless dispersing agent does not have a restriction | limiting in particular, it is 0.1-15 mass% normally on the basis of the composition whole quantity.

Examples of the antioxidant that can be contained in the lubricating fluid composition of the present invention include generally known antioxidants. For example, monophenol antioxidants such as 2,6-di-tert-butylparacresol; 4 Bisphenol-based antioxidants such as 4,4'-methylenebis (2,6-di-tert-butylphenol); octyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate, (3-methyl Hydroxyphenyl group-substituted fatty acid ester antioxidants such as -5-tert-butyl-4-hydroxyphenyl) propionate; Amine antioxidants such as (alkyl) phenyl-α-naphthylamine and dialkyldiphenylamine; Copper-based and molybdenum-based And other metal antioxidants.
The content in the case of containing an antioxidant is not particularly limited, but is usually 0.1 to 5% by mass based on the total amount of the composition.
Examples of the friction modifier that can be contained in the lubricating fluid composition of the present invention include generally known friction modifiers, such as molybdenum dithiocarbamate, molybdenum dithiophosphate, and an alkyl group or alkenyl group having 6 to 30 carbon atoms. Examples include fatty acid esters, aliphatic alcohols, aliphatic amines, aliphatic ethers, aliphatic imides, aliphatic hydrazides, and aliphatic ureas.
Although content in the case of containing a friction modifier is not particularly limited, it is usually 0.1 to 5% by mass based on the total amount of the composition.

Examples of the viscosity index improver that can be contained in the lubricating fluid composition of the present invention include generally known viscosity index improvers, such as polymers of one or more monomers selected from various methacrylic esters or So-called non-dispersed viscosity index improvers such as copolymers or hydrogenated products thereof, or so-called dispersed viscosity index improvers obtained by copolymerizing various methacrylic acid esters containing nitrogen compounds, non-dispersed or dispersed ethylene- Examples thereof include α-olefin copolymers or hydrogenated products thereof, polyisobutylene or hydrogenated products thereof, hydrogenated products of styrene-diene copolymers, styrene-maleic anhydride ester copolymers, and polyalkylstyrenes. Here, propylene can be illustrated as the α-olefin.
Although there is no restriction | limiting in particular in content in the case of containing a viscosity index improver, It is 0.1-20 mass% normally on the basis of the composition whole quantity.
Examples of the antiwear agent that can be contained in the lubricating fluid composition of the present invention include generally known antiwear agents, and antiwear agents other than the phosphorus-containing compounds listed above, for example, disulfides, sulfurized olefins, sulfides. Sulfur-containing compounds such as fats and oils, dithiocarbamate, zinc dithiocarbamate and the like can be mentioned.
Although content in the case of containing an antiwear agent is not particularly limited, it is usually 0.005 to 10% by mass based on the total amount of the composition.
Examples of the pour point depressant that can be contained in the lubricating fluid composition of the present invention include generally known pour point depressants, such as poly (meth) acrylate pour point depressants.
When the pour point depressant is contained, the content is usually 0.01 to 5% by mass based on the total amount of the composition.

Examples of the demulsifier that can be contained in the lubricating fluid composition of the present invention include generally known demulsifiers, such as polyalkylenes such as polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene alkyl naphthyl ether, and the like. Glycol-based nonionic surfactants; sorbitan monooleate.
Examples of the metal deactivator that can be contained in the lubricating fluid composition of the present invention include generally known metal deactivators such as imidazoline, pyrimidine derivatives, alkylthiadiazoles, mercaptobenzothiazoles, benzotriazoles or derivatives thereof. 1,3,4-thiadiazole polysulfide, 1,3,4-thiadiazolyl-2,5-bisdialkyldithiocarbamate, 2- (alkyldithio) benzimidazole, β- (o-carboxybenzylthio) propiononitrile. .
Examples of the antifoaming agent that can be contained in the lubricating fluid composition of the present invention include generally known antifoaming agents, such as silicone, fluorosilicol, and fluoroalkyl ether.
Examples of the corrosion inhibitor that can be contained in the lubricating fluid composition of the present invention include benzotriazole, tolyltriazole, thiadiazole, and imidazole compounds.
Examples of the rust preventive agent that can be contained in the lubricating fluid composition of the present invention include petroleum sulfonate, alkylbenzene sulfonate, dinonylnaphthalene sulfonate, alkenyl succinate, and polyhydric alcohol ester.
When these additives are contained, the content is usually 0.005 to 5% by mass for the demulsifier, corrosion inhibitor, and rust inhibitor, respectively, and 0.005 for the metal deactivator, based on the total amount of the composition. It is usually 0.0005 to 1% by mass for an antifoaming agent.

The lubricant and lubricating fluid composition of the present invention are not only used for reducing friction of general iron-based, aluminum-based, magnesium-based and other sliding materials, but also various sliding materials such as carbon-based hard thin film-coated sliding materials. It is also effective in reducing the friction of fluororesin-based sliding materials.
The lubricant and lubricating fluid composition of the present invention are used for internal combustion engines such as automobile engines, motorcycle engines, marine engines, and power generation engines; automatic transmissions, manual transmissions, continuously variable transmissions, final reduction gears, etc. Drive transmission devices: compressors, turbines, industrial gears, refrigerators, bearings, paper machines, sliding guide surfaces, cutting, pressing, rolling, metal working, shock absorbers, construction machinery, hydraulic equipment, machine tools, hard disks, etc. It can be used for sliding surfaces for applications.

The content of the present invention will be described more specifically with reference to examples and comparative examples, but the present invention is not limited to these examples.
Examples 1-4, Comparative Examples 1 and 2
Lubricating fluid compositions according to the present invention having compositions shown in Table 1 (Examples 1 to 4) and comparative lubricating fluid compositions (Comparative Examples 1 and 2) were prepared.
The following evaluation tests were performed on the obtained compositions. The results are shown in Table 1.
(SRV friction test)
A test piece (cylinder / disk, SUJ-2) for SRV friction tester manufactured by Optimol Co., Ltd. was made to have a roughness finish Ra of 0.2 μm or less, and each lubricating fluid composition was dropped onto the test piece and set on the tester. The coefficient of friction after 30 minutes was measured under the test conditions of a temperature of 80 ° C., a load of 30 N, an amplitude of 3 mm, and a frequency of 50 Hz.

The hydroxy group-containing amine compounds (I) and (II) in Table 1 were synthesized by the following procedure.
<Synthesis of Hydroxy Group-Containing Amine Compound (I)>
61.52 g of oleylamine was placed in a 500 ml four-necked flask and dissolved in 200 ml of dehydrated toluene in a nitrogen atmosphere at room temperature. Next, 17.04 g of glycidol was dissolved in 34.72 ml of dehydrated methanol, added dropwise to the flask over 2 hours, and heated and maintained at 80 ° C. for 2 hours while continuing to stir. The reaction was completed as methanol was distilled off. . Toluene was distilled off with a rotary evaporator maintained at 80 ° C. to obtain 78.47 g of N- (2,3-dihydroxypropyl) oleylamine as a target product.
<Synthesis of hydroxyl group-containing amine compound (II)>
Instead of oleylamine, 77.54 g of octylamine was used and the amount of glycidol used was equimolar with that of octylamine. 121.0 g of 2,3-dihydroxypropyl) octylamine was obtained.

表１から明らかな通り、本発明の潤滑剤を含む潤滑流体組成物は、本発明の潤滑剤を含まない潤滑流体組成物に比べ、優れた摩擦低減効果を有していることがわかる。特に長鎖炭化水素基を有する本発明の潤滑剤を含む実施例１の潤滑流体組成物がより優れた摩擦低減効果を示すことがわかる。また、ＺＤＴＰを含有する実施例３及び４の潤滑流体組成物よりも低リン化された実施例１の組成物の方が優れた低摩擦性を示すことがわかる。

As is apparent from Table 1, the lubricating fluid composition containing the lubricant of the present invention has an excellent friction reducing effect as compared with the lubricating fluid composition not containing the lubricant of the present invention. In particular, it can be seen that the lubricating fluid composition of Example 1 containing the lubricant of the present invention having a long-chain hydrocarbon group exhibits a more excellent friction reducing effect. In addition, it can be seen that the composition of Example 1 that is low-phosphorized than the lubricating fluid compositions of Examples 3 and 4 containing ZDTP exhibits superior low friction properties.

Claims (3)

A lubricant comprising a hydroxy group-containing amine compound represented by the formula (1).
R ¹ —N (R ² ) —R ³ — (OH) n (1)
(In Formula (1), R ¹ is an alkyl group or alkenyl group having 6 to 30 carbon atoms, R ² is hydrogen, an alkyl group or alkenyl group having 1 to 30 carbon atoms, —R ⁴ — (OH) m, or — ^{(R 5 O) t-H} ( wherein, residue R ⁴ is other than a hydroxy group from monohydric or polyhydric alcohols having 1 to 10 carbon atoms, R ⁵ is an alkylene group having 1 to 4 carbon atoms, m or t independently represents an integer of 1 to 10), R ³ represents a residue obtained by removing a hydroxy group from a monovalent or polyhydric alcohol having 1 to 10 carbon atoms, and n represents an integer of 1 to 10).   A lubricating fluid composition comprising: a lubricating fluid base material comprising one or more selected from water, alcohol, carboxylic acid, mineral oil, synthetic oil and oil and fat; and the lubricant according to claim 1. .   Phosphorus-containing compounds, metal detergents, ashless dispersants, antioxidants, friction modifiers, viscosity index improvers, antiwear agents, fluidity improvers, demulsifiers, metal deactivators, antifoaming agents, corrosion inhibitors The lubricating fluid composition according to claim 2, comprising at least one selected from an agent and a rust inhibitor.