WO1994017163A1

WO1994017163A1 - Lubricant for a two cycle engine

Info

Publication number: WO1994017163A1
Application number: PCT/JP1994/000063
Authority: WO
Inventors: Mitsuaki Ishimaru; Mineo Kagaya; Noboru Ishida
Original assignee: Nippon Oil Co., Ltd.
Priority date: 1993-01-20
Filing date: 1994-01-19
Publication date: 1994-08-04
Also published as: EP0636680A1; EP0636680A4; JPH06212182A

Abstract

A lubricant for a two cycle engine having as a basic oil a polyoxyalkylene glycol derivative expressed by general formula (1) which can realize, when used to lubricate bearing portions and sliding portions of the two cycle engine, remarkable reduction in generation of exhaust smoke, improvement in start-up capability, improvement in cleanability of preventing clogging of an exhaust system with carbon, improvement in cleanability inside the engine at high and low temperatures and improvement in withstand-load properties.

Description

--Itoda »

2 Lubricating oil for cycle engines

Technical field

The present invention relates to a two-cycle engine lubricating oil. More specifically, the emission of exhaust smoke (smoke) is remarkably low, and the engine startability is low. Excellent cleanliness to prevent plugging of the power system in the exhaust system, excellent high-temperature cleanliness and low-temperature cleanliness in the engine, and more It relates to two-cycle engine lubricating oil with excellent loadability.

Background art

2 In the case of a cycle engine, the unburned engine lubricant is discharged with the exhaust gas due to the lubrication mechanism. It is the cause of the outbreak.

Smoke is expected to be as small as possible from the standpoint of environmental pollution, and in Japan, the generation of smoke is already in mineral base oil. For low-smoke type two-cycle engines with a base oil based on less polybutene or polysobutylene Lubricants are widespread in the market.

Mineral base oils because polybutene is a sticky substance, which increases the friction between piston and cylinder The engine output is inevitably reduced as compared to that of the previous model. --For mowers, chain saws, generators, and other types of mowers (starting method in which a string is wrapped around the pulley and pulled). In some cases, the engine is difficult to control when starting the engine, or there is a problem in that it is difficult to operate.

Et al Po Li butene down is set to not click the Ri or mosquitoes over Bonn packed the exhaust system Ri by mineral oil to cause this LesゝRu force ^s', starting one-stop run line is not abundance, For example, in a newspaper delivery cycle, it was reported that at low temperatures, rather than mineral oil, more emulsified sludge was produced than mineral oil. You. Clogging of this exhaust system with carbon or emulsion can adversely affect engine combustion and reduce output.

As a result, there is little smoke and the engine output is low, as seen in smokeless oils such as polybutene. Power of the system—The development of a two-cycle engine lubricating oil with improved cleanliness that improves clogging of the bon was required.

The present inventors have conducted extensive research to develop lubricating oils suitable for two-cycle engines, and as a result, have obtained a polyoxyalkylene having a specific structure. When a glycol derivative is used as a base oil, the output of the engine is lower than that of a conventional two-cycle lubricating oil for cycle engines. A low-smoke-type lubricating oil for two-cycle engines with little reduction, excellent startability, and no exhaust system power-bon blockage can be obtained. The present inventors have found that the present invention has been completed. Disclosure of the invention

The present invention is based on a polyoxyalkylene glycol derivative represented by the general formula (1) (hereinafter referred to as “Component A”) as a base oil. Provide a two-cycle engine lubricating oil characterized by:

R ³ R ^s

I I

R '-O— ^ C-C-O ^ — R ² --(1) HR ^{6 In} formula ⁶ , R 1 and R 2 may be the same or different. Hydrogen, an alkyl group having 1 to 22 carbon atoms, an alkylene group having 3 to 22 carbon atoms, and a cycloalkyl group or an alkyl group having 5 to 20 carbon atoms, respectively. Alkyl cycloalkyl group, or aryl group having 6 to 20 carbon atoms, alkyl aryl group or aryl alkyl group Specifically, for example, hydrogen; methyl; methyl; ethyl; propyl; butyl; pentyl; hexyl; heptyl; Group, octyl group, nonyl group, decyl group, pendecyl group, dodecyl group, tridecyl group, tetradecyl group, penta Decyl group, Hexadecyl group, Heptadecyl group, Octa Alkyl groups such as decyl group, nonadecyl group, eicosyl group and isomers thereof; propyl group, isopropyl group Group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, phenyl Decenyl, Dodecenyl, Tridecenyl, Tetradecenyl Phenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, coco Alkenyl groups such as senyl group and their isomers; cyclopentyl group, cyclohexyl group, cycloheptyl group Alkyl group at the mouth of the mouth; pentyl group at the methyl mouth; ethylcyclopentyl group; propylcyclopentyl group; Cyclopentyl group, dimethylcyclopentyl group, ethymethylcyclopentyl group, phenyl pentyl group , Dipropyl pent-pentyl group, dibutyl pent-open pentyl group, methyl-cyclo-hexyl group, ethyl-ethyl pendant Group, Probi Lexicyclohexyl group, Butylcyclohexyl group, Dimethylcyclohexyl group, Ethylmethyl Doxyl mouth hexyl group, zipropiric mouth hexyl group, digylshile mouth hexyl group, methylcyclohexyl Group, ethyl cyclyl butyl group, propyl cyclyl butyl group, butyl cyclyl butyl group, dimethyl cyclyl butyl group , Ethyl methyl lip to mouth, ethyl cyclo hop to lip, dipropyl cyclo hop to lip, butyl lip to mouth Alkyl groups such as acetyl group and their isomers; phenyl group, naphthyl group (including all isomers) Which Aryl group; tril group, ethyl phenyl group, propyl phenyl group, butyl phenyl group, pentyl phenyl group, Xyl phenyl group, heptyl phenyl group, 1-octyl nonyl phenyl group, nonyl phenyl group, desil phenyl group, undecyl phenyl group, dodecyl phenyl group, dodecyl phenyl group Nil group, Xylyl group, Methylmethylphenyl group, Jethylphenyl group, Dipropylphenyl group, Dibutylphenyl group Group, methyl naphthyl group, ethyl naphthyl group, pulpnaphthyl group, butyl naphthyl group, dimethyl naphthyl group, Ethyl methyl naphthyl, dimethyl naphthyl, dipropyl naphthyl, dibutyl naphthyl and their isomers Alkyl aryl groups such as the body; benzyl groups, phenylethyl groups, phenylpropyl groups and their isomers, etc. Library Yellow Le based on that Ki out and this Ru elevation up.

In the formula (1), R ¹ and R ² are preferably hydrogen, a linear or branched alkyl group having 1 to 18 carbon atoms, or a hydrogen atom. Alkyl phenyl groups having 7 to 18 carbon atoms having a benzyl group or a linear or branched alkyl group are used. Specific examples of the group include hydrogen, methyl group, ethyl group, propyl group, butyl group, ethyl group, hexyl group, and the like. Heptyl, octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, phenyl , Triphenyl, ethylphenyl, propylphenyl, butylphenyl, pentylphenyl, hexyl Phenyl group, heptylphenyl Group, octylphenyl group, nonylphenyl group, Examples include the decylphenyl group, the dodecylphenyl group, the xylyl group, and isomers thereof.

Further, from the point of view that the purification is more excellent, R 1 in the formula (1) can be hydrogen, straight-chain or branched as R 1 in the formula (1). More preferably, it is an alkyl group having 1 to 4 carbon atoms (desirably, a straight-chain alkyl group). Specifically, mention may be made of, for example, hydrogen, methyl, ethyl, propyl, and butyl and isomers thereof. From the same point, R ² in the formula (1) is a straight-chain or branched alkyl group having 1 to 4 carbon atoms (desirably straight-chain alkyl group). A chain alkyl group), a vinyl group or a linear or branched alkyl group having 7 to 18 carbon atoms. More preferably, it is a hydrocarbon group selected from the group consisting of, for example, a methyl group, an ethyl group, and a phenyl group. Propyl group, butyl group, phenyl group, tril group, ethyl phenyl group, open phenyl phenyl group, butyl phenyl group , Pentylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, Decyl-enil group, De Shi Le full E two-group, key Shi Li etc. Lumpur groups that you good beauty this is these isomers Ru is ani-up et al.

On the other hand, in the formula (1), R ³ .R ⁴ .R ⁵ and R 6 may be the same or different, and are each a hydrogen, a methyl group or a hydrogen group. Ethyl group, force, ό R 3, R 4, R 5 --And the total carbon number of R 6 is 1 or 2. Further, in the present invention, a is an integer from 1 to 200, preferably from 2 to 100, and more preferably from 5 to 50. Best form for carrying out the invention Polyoxylary grease used as a base oil with the two-cycle engine lubricant of the invention The call conductor is as described above, and has the following general formula (5)

R ^{3 5}

I I

— C-C-0 ·--· (5)

It has a polyoxyalkylene chain represented by R ⁴ ^RG , which is

R ³ R ⁵ -C-C-0--… (6)

① It is represented by the general formula (6) and is selected from it

A homopolymer having one structural oxyalkylene group as a single structural unit,

(2) It has two or more different types of oxyalkylene groups represented by the general formula (6) and selected from among them as structural units. A random copolymer or a block copolymer (in this case, a represents the total degree of polymerization of the oxyalkylene group represented by the general formula (6)), or Is a mixture of two or more polymers selected from ③ ① to ② --

(In this case, a represents the total average degree of polymerization of the oxyalkylene group represented by the general formula (6) in the polymer mixture, respectively.)

It means that something is induced by force.

In addition, the viscosity of component A is arbitrary. Viscosity at 100 ° C 1 to 100 mm 2 / _s , preferably 5 to 50 mm 2 / s is practical. It is preferably used.

The two-cycle engine lubricating oil of the present invention uses component A as a base oil. Mineral oil-based lubricating oil that dissolves in component A as required. It is also possible to mix the synthetic lubricating oil and the mineral oil diluent alone or in combination of two or more with component A as a base oil. The total mixing ratio of these other base oils is arbitrary as long as it does not impair the properties of the two-cycle engine lubricating oil of the present invention. It is 100 parts by weight or less, preferably 100 parts by weight or less, more preferably 50 parts by weight or less.

The two-cycle engine lubricating oil of the present invention exhibits excellent performance even when component A is used alone without using any additives. At least one nitrogen-containing compound selected from the following (a) to (d) with the aim of further enhancing the cleanliness of a certain force ^s Hereafter, this will be referred to as “Component B”).

(a) — a nitrogen-containing compound represented by the general formula (2)

"Component (a)") _{H- e NH - C 2 H,} - - N H- C- - O - CH - CH - ^ - OR 7 -. ·· (2) b II II

OR ⁸ R ⁹

(Wherein, is an alkyl group having 1 to 22 carbon atoms, an alkylene group having 3 to 22 carbon atoms, a cycloalkyl group having 5 to 15 carbon atoms) Is an alkylcycloalkyl group, some are, are C6 to C18 aryl groups, alkylaryl groups, or arylaryl groups. And R ⁸ and R 9 are the same or different, and may be hydrogen or an alkyl group having 2 to 6 carbon atoms, respectively. And the total number of carbon atoms of R8 and R9 is 2 to 8, b is an integer of 1 to 8, and c is an integer of 5 to 40.)

(b) Borides of the nitrogen-containing compounds of (a) (hereinafter referred to as component (b))

(c) — a nitrogen-containing compound represented by the general formula (3) (hereinafter, referred to as “component (c)”)

H- fN- [(-R1D-NH-) _d . (-R1D- τN-) _e ] -H... (3)

(In the formula, X represents a hydrogen atom or an acyl group having 6 to 30 carbon atoms derived from a fatty acid, and Y represents 6 to 30 carbon atoms derived from the fatty acid. And R io represents an alkylene group having 2 to 4 carbon atoms, d is an integer of 0 to 11 and e is an integer of 0 to 11; 2 ^ d + e ^ l 1, provided that at least one acyl group is contained in one molecule. --Yes. )

(d) Borides of the nitrogen-containing compound of (c) (hereinafter referred to as “component (d)”).

The component (a) of the present invention is a nitrogen-containing compound represented by the following general formula (2).

_{H - - NH - C 2 H} , ^ - NH - C- ^ O - CH - CH ^ - OR 7 - ... (2)

. ^b II II

OR ⁸ R ⁹

In the formula (2), R is an alkyl group having i to 22 carbon atoms, an alkylene group having 3 to 22 carbon atoms, and a cyclized alkyl having 5 to 15 carbon atoms. Or an alkylcycloalkyl group, or an aryl group having 6 to 18 carbon atoms, an alkylaryl group or an aryl group. It shows a charcoal hydrogen group selected from an alkyl group, and specifically, for example, a methyl group, an ethyl group, a propyl group, and a butyl group. Group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, pendyl group, dodecyl group, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl Sil group, Ecosil group and this Alkyl groups such as isomers thereof; propyl group, isopropenyl group, butenyl group, pentenyl group, hexenyl group, Petuyl group, octenyl group, nonenyl group, decenyl group, undecenyl group, dodecenyl group, tridecenyl group, tetra Radi-senyl group, penta-decenyl group, hexa-decenyl group, hepta-decenyl group, octa-decenyl Alkenyl groups such as--group, nonadecenyl group, eicosenyl group and isomers thereof; cycle pentyl group, cycle mouth Cycloalkyl groups such as hexyl groups and cycloheptyl groups; methylcyclopentyl groups, ethylcyclopentyl groups, Probicyclopentyl, butylcyclopentyl, dimethylcyclopentyl, ethylmethylcyclopentene Tyl group, Jethyl cyclopentyl group, Jipropyl cyclopentyl group, Jibutyl cyclopentyl group, Methyl silicon mouth Hexyl group, ethyl silk mouth Hexyl group, propyl cyclohexyl group, butyl cyclohexyl group, dimethyl cyclo Hexyl group, Chile methyl cyclohexyl group, getyl cyclohexyl group, dipropyl mouth mouth hexyl group, dibutyl cyclohexyl group Syl group, methylcycloheptyl group, ethylcycloheptyl group, propylcycloheptyl group, butylcycloheptyl group , Methyl methyl cyclo-ethyl group, methyl methyl cyclo-ethyl group, methyl cyclo-mouth to ethyl group, di-methyl cyclo-mouth Alkylcyclohexyl groups such as heptyl group, dibutylcycloheptyl group and isomers thereof; phenyl group, na group Aryl groups such as butyl groups (including all isomers); tolyl groups, ethylphenyl groups, propylphenyl groups, and butyryl groups Any Phenyl, phenylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl Group, decyl phenyl group, benzyl group --Genyl group, dodecyl phenyl group, xylyl group, ethylmethyl phenyl group, dimethyl phenyl group, dipropyl group Phenyl, dibutyl phenyl, methyl naphthyl, ethyl naphthyl, propyl naphthyl, butyna naphthyl Group, dimethyl naphthyl group, ethyl methylene naphthyl group, dimethyl naphthyl group, dipropyl naphthyl group, diptyl group Alkyl aryl groups such as naphthyl group and their isomers; benzyl group, phenylethyl group, phenylpropyl group It is possible to enumerate arylalkyl groups such as groups and their isomers.

(2) In the formula, a linear or branched alkyl group having 1 to 18 carbon atoms, a phenyl group, or a linear or branched chain. Alkyl phenyl groups having 7 to 18 carbon atoms and having an alkyl group are preferably used, and as these groups, specifically, For example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a decyl group Group, dodecyl group, tetradecyl group, hexadecyl group, octadecyl group, phenyl group, tril group, ethyl phenyl group Group, propyl phenyl group, butyl phenyl group, pentyl phenyl group, hexyl phenyl group, heptyl phenyl group Group, octylphenyl group , Nonylphenyl, decylphenyl, dodecylphenyl, xylyl and isomers thereof. You. --Also, R 8 and R 9 in the formula (2) may be the same or different, each of which is a hydrogen or a carbon number of 2 to 6 respectively. · the Ri Ah Le group, or one R ⁸ and the total carbon number containing 2-8 of R ^9, good or to rather is Ru Oh 2-6. Examples of R 8 and R 9 include, for example, an ethyl group, a port pill group, a butyl group, a pentyl group, a hexyl group and These isomers and the like are listed, and particularly, an ethyl group is preferably used.

— On the other hand, in the formula (2), b is an integer of 1 to 8, preferably 1 to 6, and c is an integer of 5 to 40, preferably 10 to 30. Is shown.

The component (b) according to the present invention is a compound obtained by reacting the component (a) with a boronizing agent.

The boriding agent to be used here includes all boriding agents which form a nitrogen-containing and boron-containing compound in reaction with the component (a). You. Is a boric iodinating agent, in particular if example embodiment, Oh Le preparative boric acid (H _₃ B 0 _3), meta boric acid (HB 〇 _2), the four-boric acid (H ₂ b ₄ 0 _7), acid of boric elements of etc. anhydrous boric acid, Sani匕boric element (b ₂ 03) of Yo I Do boric Moto Sani匕物, full Tsu Lee spoon boric iodine , Boron nitride such as boron chloride, boron bromide, ammonium boride, ammonium borate, sodium borate, boron Salts of boric acid, such as potassium sulphate, and the general formula (7)

_h · · · (7) (17) In the formula (7), R ¹⁷ is an alkyl group having 1 to 6 carbon atoms, g is 1 to 3, and h is Represents an integer from 0 to 2 and g + h = 3), and more specifically, mono-, g- and trimethyl-poles, mono-, di- One- and three-port rates, mono-, tri-, and tri-prop rates, mono-, one-, and tributyl ports Rate, Mono, Ji and Tri-Pentle Volat, Mono, Ji and Tri-Hexile Volt, etc. These mixtures and the like are preferably used. Among these, the boriding agent of the present invention is more preferable than the acid of boron and the lower alkyl ester power s of boric acid. Particular preference is given to rutoboric acid, lower alkyl esters of boric acid and mixtures thereof.

The amount of the boriding agent at the time of boriding is determined by an arbitrary force ^s , and the boriding content of the finally obtained borohydride s 0.05 to "7. It is preferable to use a sufficient amount of a boron-containing agent so as to have a weight of 6. The nitrogen-containing nitrogen atom represented by the general formula (2) is generally used. The number of boron atoms in the boronizing agent per one nitrogen atom in the compound should be 0.05 to 10 and preferably 0.1 to 2. You.

The boriding with the boriding agent is carried out by heating the nitrogen-containing compound represented by the general formula (2) together with the boriding agent. In the boron iridone reaction, water, alcohol, hydrocarbon, and a mixture thereof may coexist as necessary. Water and / or alcohol is a "reactive solvent" that reacts with the boriding agent to form an intermediate reactant that is preferred for the boriding reaction. It is effective in improving the boriding reaction yield. Hydrocarbons are also used as "non-reactive solvents". In addition to their role as solvents for the boron iridation reaction, the water produced in the reaction is azeotropically generated It also has the effect of removing it outside.

The alcohols include, specifically, methanol, ethanol, pro-no-nor, iso-pro-no, ^zero- no, and n-butano. , Sec — butanol, pentanol (amyl alcohol, isoamyl alcohol), hexanol, ethyl Recalls, propylene calls, butyl calls, penthole calls, hex calls, etc. It is preferably used. Hydrocarbons having a boiling point of 60 ° C or more are preferred, and specific examples include benzene, toluene, xylene, benzene, and rigs. Loin, mineral spirits, cleaning solvents, petroleum naphtha, cyclohexane, hexan, mineral oil, mineral oil naphtha It can be used for various purposes such as sulfur fraction, kerosene fraction, gas oil fraction, and lubricating oil fraction.

The reaction temperature at the time of boriding must be high enough to allow the boriding agent to react with the nitrogen-containing compound represented by the general formula (2). The force must not be so high as to cause decomposition of the reactants or products. Suitable reaction temperatures are usually between 50 and 250 ° C., preferably between 80 and: I 80. In C - - is there. Usually, reflux is performed at the boiling point of the solvent. Since the boration reaction is generally completed in a short time, the reaction time is usually 0.5 to 8 hours, preferably 2 to 6 hours. After the boriding reaction is completed, the reaction mixture is heated to distill off the water formed by the reaction and, if used, the solvent as described above. . Here, the water is usually dehydrated with a dehydrating agent such as sodium sulfate and magnesium sulfate. Then, if necessary, the reaction mixture is subjected to benzene, toluene, xylene, hexane, benzene, rubber oil for petroleum, petroleum petroleum Either dilute with any organic solvent and remove the unreacted borating agent by filtration or solvent extraction, or perform a purification operation such as vacuum distillation as appropriate. The resulting component (b) can be obtained. The ratio of the number of nitrogen atoms to the number of boron atoms in the finally obtained nitrogen-containing boron-containing compound is determined by the ratio of the boron-containing compound to the nitrogen-containing conjugate in the boriding step. It can be varied arbitrarily by varying the amount of nucleating agent, but usually from 1: 0.05 to 5, preferably 1: 0. 1-2. The component (c) of the present invention is a nitrogen-containing compound represented by the following general formula (3).

X Y

HN- [(-R1D-NH-) c-(-Rio-λ-) _e ] — H... (3)

(3) In the formula, X is a hydrogen atom or a fatty acid derived from a fatty acid having 6 to 30 carbon atoms, preferably 12 to 20 carbon atoms. Y represents an acyl group having 6 to 30 carbon atoms, preferably 12 to 20 carbon atoms, derived from a fatty acid; and Rio represents a C 2 to C 4 carbon atom. It preferably represents a few alkylene groups. d is 0 to: 1 1, preferably 3 to 11, and more preferably an integer of 4 to 11, and e is an integer of 0 to 11, where 2 ≤ d + e ^ 1 1. However, one molecule has at least one acyl group. In X or Y, the fatty acids include saturated fatty acids having 6 to 30 carbon atoms and / or unsaturated fatty acids, especially those having 12 to carbon atoms. 20 saturated fatty acids are preferred, and preferred examples are dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, and hexadecanoic acid. Sadecanic acid, Heptadecanoic acid, Octadecanoic acid, Nonadecanoic acid, Eicosanoic acid, Isododecanoic acid, Isotridecaic acid Acid, isotetradecanoic acid, isopene decanoic acid, isohexadecanoic acid, isoheptadecanoic acid, isooctadecanoic acid Examples thereof include fatty acids having a linear or branched structure, such as carboxylic acid, isononadecanoic acid, and isoeicosanoic acid, and mixtures thereof. Examples of the alkylene group of R ¹⁰ include an ethylene group, a propylene group, a trimethylene group, a tetramethylene group, and a butylene group. , I Seo Breakfast Chi-les-down based on your good beauty main Chi Le door Li main Chi-les-down group, and the like force ^s 'ani-up we are Ru force', et Ji-les-down group in this, profile pin-les-down based on Preferred are trimethylene bases, and especially preferred are ethylene groups.

As the component (c) used in the present invention, a commercially available product is used. It is also possible to use a material obtained by assembling a polyalkylene polyamine. In this case, the polyalkylenepolyamine is represented by the general formula H ₂ N (-Rio-NH) .—— H ·. · (8)

I

What is represented by can be used favorably. In the formula (8), R io is the same as R io in the general formula (3), i is 2 to 11, preferably 3 to 11, and more preferably 4 to 11. ~: An integer of 1 1 Specific examples of polyalkylene polyamine include polyethylene triamine, triethylene tetramine, tetraethylene, and tetraethylene. Pentamin, Pentaethylene Hexamin, Hexaethylene Heptamine, Heptaethylene Octamin, Octaethylene Lennonamine, nonaethylenedicene, deethylenedidecane, diethylenedidecane, dipropylene Triamin, Tripropylene, Tetrapropylene, Pentram Pen, Pen Pen, Propylene Propylene Heptamine, Hep Evening Propylene Octamin, Oktapropylen Nonamin, Nonapropylen Decamin , De cap Pyramid decane, pendant propylen decamine, tri (trimethylene) triamin, tri (trimethylene) Tetramin, Tetra (Trimethylene) Pen Yu Min, Pen Yu (Trimethylene) Hexamin, Hexa (Trimethylene) ) 夕ミ、、トチヘ、ヘ (Trimethylene) Nonamin, Nona (Trimethylen) Decamin, Deca (Trimethylen) デ Decamin, デTrimethylene) Dodecamin.

— On the other hand, as an acylating agent for assimilating a polyalkylene polyamine, the number of carbon atoms as described above is 6 to 30. Fatty acids, preferably 12 to 20 saturated fatty acids, or fatty acid derivatives such as fatty acid halides and anhydrides are preferably used.

The amount of the acylating agent used when assembling a polyalkylene polyamine is based on 1 mol of the polyalkylene polyamine. The power s preferred is 0.1 to 1 mol. The reaction conditions such as the reaction temperature, reaction time, catalyst and solvent should be in accordance with the usual conditions of the acylation reaction, and the polyalkylene used can be used. It is selected as appropriate according to the polyamine compound.

In addition, the component (d) in the present invention is a compound obtained by reacting the component (c) with a boron compound. The method of boron iodide and the method of boron iodide used here are the same as those used for the component (b). However, the boronizing agent is used in an amount of 0.05 to 5.0 mol, preferably 0.1 to 3.0 mol, per mol of the component (c). You. Further, the number of boron atoms in the boriding agent per one nitrogen atom in the component (d) is f 0.02-: I 0, preferably 0. 0 5-5.0, more preferably 0.1 to 2 You.

Component B is lubricating oil for two-cycle engines, with component A as the base oil, either as is or diluted with a solvent such as kerosene or lubricating oil To obtain a lubricating oil composition for two-cycle engines. The content of the component B is 0.5 to 30% by weight, preferably 1 to 20% by weight, and more preferably 3 to 10% by weight based on the total amount of the composition. You. If the content does not reach this range, the effect of adding this compound to improve the cleanliness is poor, while if the content exceeds this range. Is not economically disadvantageous because the effect of improving the cleanliness cannot be obtained in proportion to the amount added, and so both are not preferred.

The method of mixing the component B and the component A to obtain the lubricating oil composition for two-cycle engine according to the present invention is optional. Force Usually, the temperature is 20 to 80 ° C. It can be obtained by mixing both components in 30 minutes to 3 hours.

In the two-cycle engine lubricating oil composition of the present invention, a polyoxyalkylene glycol represented by the general formula (4) is particularly preferred. Base oil as the base oil,

(In the formula, R ^{11 and} R i 2 may be the same or different, and may be hydrogen, an alkyl group having 1 to 4 carbon atoms, respectively. Is an aryl group having 6 to 20 carbon atoms, an alkyl aryl group, or an aryl alkyl group, and is one of R11 and R12. One or both of them are an aryl group having 6 to 20 carbon atoms, an alkylaryl group or an arylalkyl group. R 13, R 14, R 15 and R i 6 may be the same or different, each being a hydrogen, a methyl group or an ethyl group. Oh Ri, or one _{R 1 3, R 1 4,} R 1 5 your good beauty R i 6 total carbon was prime number power 1 or of Ri Oh at 2, ί is Ru Oh 1 to 2 0 0 integer) The composition contains at least one nitrogen-containing compound selected from the above-mentioned components (c) and (d), and thus has a low-temperature purification property in addition to a high-temperature purification property. A two-cycle lubricating oil composition having excellent cleanliness can be obtained.

In addition, if necessary, a known antioxidant to enhance the superior performance of Honoki Akira's two-cycle engine lubricating oil. , Load-bearing additives, metal-based detergents, ashless dispersants, metal deactivators, viscosity index improvers, pour point depressants, defoamers and other lubricating oil additives alone Or two or more kinds can be added in combination. Except for the defoamer, these additives stably dissolve in the base oil of the two-cycle engine lubricating oil of the present invention and produce turbidity and precipitates. It is important that you do not make any mistakes, and if you do add it, you need to be very careful in its selection. Further, the amount of these additives to be added is arbitrary. Usually, the total content of the additives is 20% by weight or less based on the total amount of the composition. It is preferable to add []

The two-cycle engine according to the present invention is an engine having a mechanism that completes combustion by one rotation of the crankshaft. 2 The cycle engine is used for various purposes, and there are no special restrictions. For example, motor cycles, carts, snowboards, outboard motors, motor boats, marine skis, generators, chains These include gas saws, lawn mowers, sprayers, unmanned light aircraft and fire pumps.

The two-cycle engine lubricating oil or the two-cycle engine lubricating oil composition of the present invention is used to lubricate the two-cycle engine. There is no restriction on the method of sliding and power ^s '. For example, the use of the above-mentioned two-cycle engine lubricating oil or two-cycle engine lubricating oil composition (hereinafter referred to as “oil”) As a supply method, oil is mixed in advance with fuel at a specified ratio, and the mixture is put into the fuel tank, and the air-fuel mixture is used as a precompression chamber. The mixing method of feeding into the rank case, the fuel and oil are put in separate tanks, the oil tank power, and the oil There is a separation method in which the pump is directly pumped to the crankcase. These methods introduce oil into the crankcase and lubricate the bearings and sliding parts in the engine. The bearings used here include crank bearings, low end bearings, and large end bearings.ピ and the piston pin are raised. Also, as a sliding part Includes pistons, cylinders, and piston rings.

( Example )

Hereinafter, the ability to explain the content of the present invention more specifically with reference to Examples and Comparative Examples, and the present invention is not limited to these contents. What is it?

In addition, A to I (component A) used as the base oil in the examples are as shown in Table 1 in which R 1-R 6 and a in the general formula (1) of the component A. It has a structure or a number.

table 1

*: CsH-is an alkyl group derived from butylene trimer.

3 R ^s

**: The polyoxyalkylene group represented by the general formula "^ c-C—0 → ~

R ¹ R ⁶

CH ₃ H

Oxib D pyrene group — C— C-0-8 (average value) and

H H

C ₂ H ₅ H

Oxybutylene ¾-C-C-0-8 (average value).

HH Further, the nitrogen-containing compound A (corresponding to the component (a)) used in the examples is represented by the following chemical formula (9)

C H

NH 2-C ₂ H,-NH-C— (-0-CH-CH ₂ 0-(O = 25

II I "

0 A compound represented by C ·, H, (9), and a borohydride of the nitrogen-containing compound A (corresponding to the component (b)) used in Examples. Is a product obtained by boriding the above-mentioned nitrogen-containing compound A by the following method.

Honey

1 liter flask with a cooler equipped with a trap tube, a nitrogen inlet tube, a thermometer and a stirrer containing nitrogen 0 g and tail le door boric acid 1 0.1 to 6 g input is, you start the nitrogen adsorption have included in the room rate only force ^s et al stirring and raising the temperature of the. The reaction is carried out at a reaction temperature of 110 ° C for about 3 hours, and the reaction is stopped when 3 mL of distillate is distilled into the trap tube. Next, the reaction mixture in the flask was transferred to a 1-liter eggplant-shaped flask, and distillation was performed for 1 hour under the conditions of 120 t and D.ImmHg to obtain a yellow transparent substance. Obtained was a clear viscous substance, i.e., a borohydride (boric acid-modified product) of the nitrogen-containing compound A. This filtrate and the elemental analysis was Tsu line of this compound, nitrogen 1.6 weight ^_0/0 Ri Oh in your good beauty e © containing 0.5 9% by weight, Ru is the table in the following chemical formula (1 0) It was a dagger. CH

_{_{_{HB0 2 -NH 2 -C 2 H4-}}} NH-C- -0-CH- CH 2 → -0- (o: m = 2 5

OC ₂ H. (1 0) In addition, the actual施例(the equivalent to Ingredient (C)) 1 containing nitrogen compound used in B under Symbol of formula (1 1)

Which is obtained by the following method.

Synthesis example

100 Oml with stirrer, backflow cooler, thermometer, and nitrogen inlet tube. 9 g), sodium hydroxide 10% solution 20 O ml and benzene 30 O ml were taken, and the flask was cooled to 5 ° C or less in an ice bath. . To this, 2 mol (60.5 g) of isooctadecanoic acid chloride was added dropwise over 1 hour, and after completion of the addition, the temperature was kept at 5 ° C or less. After stirring for 1 hour at, the addition was started, reflux was performed at the boiling point of benzene for 1 hour, and the reaction was stopped. After cooling, the contents of the reaction vessel were transferred to a 100 ml separating funnel, and the lower layer was separated. The upper benzene layer was washed five times with 300 ml of pure water. After dehydration with anhydrous sodium sulfate, benzene was removed to obtain a pale yellow transparent viscous liquid. The yield is

It was 6 8 g. Elemental analysis of the product indicated that carbon was

75.2 wt%, hydrogen 13.1 wt%, nitrogen 9.2 w t%.

The borides of the nitrogen-containing compound B used in the examples are those obtained by subjecting the above-mentioned nitrogen-containing compound B to boron elimination by the following method. .

Boronization

Between the flask and the backflow cooler, a 500 ml reactor similar to the synthesis example, incorporating a trap of the water to be produced, containing the sample obtained in the synthesis example. The nitrogen compound B was weighed to 50 g, and 300 ml of toluene and 0.14 mol (8.6 g) of boric acid were added. Heating and stirring were started, reflux was carried out at the boiling point of toluene, and the heating was stopped at a point (about 3 hours) when about 2 ml of generated water was distilled off. After allowing to cool, the contents were dehydrated with anhydrous sodium sulfate, and toluene was distilled off.

The obtained reaction product was a more viscous liquid than the nitrogen-containing compound B obtained in the synthesis example.

Examples 1 to 17 and Comparative Examples 1 to 4

By blending the respective components shown in Table 2, lubricating oils for two-cycle engines according to the present invention were prepared as Examples 1 to 1 1.

Performance evaluation test

The following performance evaluation tests were conducted on the two-cycle engine lubricant oil according to the present invention shown in Table 2, and the results are also shown in Table 2. .

Mineral oil (Comparative Example 1), polybutene (Comparative Example 2) A similar performance evaluation test was performed on commercially available two-cycle engine oil (Comparative Examples 3 and 4), and the results were also evaluated. Also shown in Table 2.

(1) Smoke (exhaust smoke) test

2 Use a motor cycle (air-cooled, 49 cc) equipped with a cycle engine, and observe the exhaust smoke concentration (smoke) from the muffler. It was visually evaluated. The criteria for Nao Smoke are expressed in six levels from 0 to 5 (best = 0), and under three operating conditions (40 km at idling, sudden start). / h during normal running).

(2) Startability (startability) test

2 Use a motor cycle (air-cooled, 49 cc) equipped with a cycle engine. After traveling about 10 km on the road, turn off the motor cycle at 1 o'clock. It was left in the interim room, and further left at 15 ° C for 3 hours. Next, a constant current (120 A) is applied to the cell motor from outside (outside the low-temperature room) for 10 seconds to start the engine, and the crank force 4 The time until rotation was measured, and this time was used as a measure of startability. The shorter the time, the better the start-up. Table 2

1 10.8 "2 / _s (l OO t) 2 Ca ^ fit + ift K Ca 0.6¾t ¾%, 2 ¾ ΐτ ϋ 1. fi S%)

3) M K23.0 "2 / _s (I 0 0 t) 4) Ca ¾0.033ί S, S 0. ΙΟίΐ: β% Ca ^, 1ϊ ffi

5) Ca 0.053S%, S ¾ 0.06 SC fl% (Ca κ

High temperature cleanliness test using a motor cycle engine Examples of the present invention shown in Table 2 1. 10, 11, 15 and 17-2 The lubricating oil for cycle engines and the commercially available two-cycle engine lubricating oils of Comparative Examples 3 and 4 shown in Table 2 for comparison were used as sample oils. As a result, a high-temperature cleanliness test was conducted using a single-cycle engine.

Displacement 1 2 3 cc Single-cylinder motor — Cycle air-cooled 2 Uses a cycle engine, engine speed 500 rpm, total load, puller After the engine was operated for 5 hours under the condition of fuel: oil mixture ratio = 40: 1, the cleanliness in the engine was visually evaluated. The results are shown in Table 3. The criteria for cleanliness were expressed in 11 levels from 0 to 10 (best = 10).

Table 3 Example 1 Example 1 0 Example 1 1 Example 1 5 Example 1 Comparative Example 3 Comparative Example 4 Link ', sticky tofu ⁰ 10 10 10 10 10 5.0 5.0 Link "sticky second' 10 10 10 10 10 10 10 link "groove g :; 7.9 8.6 9.0 8.9 9.0 2.9 0 Link ', groove w 7.4 8.4 8.2 7.9 8.5 1.7 6.4 Link "Land tough ⁰ 7.2 6.9 8.0 7.0 8.1 3.8 5.9 Link', Land * Land '7.2 8.3 7.6 7.4 8.4 6.2 8.3 Piston skirt 9.1 9.6 9.3 9.3 9.5 9.8 9.6 Anne ',-Crown 5.3 5.7 7.7 6.5 7.0 1.3 3.5 Total (out of 80) 64.1 67.5 69.δ 67.0 70.5 40.7 48.7

Low temperature cleanliness test

Examples 14, 15 and 17-2 of the present invention shown in Table 2 Lubricating oil for cycle engines, and Table 2 for comparison A low-temperature cleanliness test was conducted using the commercially available two-cycle lubricating oil of Comparative Example 3 as a sample oil. In this test, the running conditions of the engine and engine where the temperature of the engine does not rise due to many start-stop types, such as a motor cycle dedicated to newspaper delivery This test assumes that The test was carried out using a generator, and after the engine was operated intermittently at around 130 ° C of plug temperature, the cleanliness inside the engine was visually evaluated. Table 4 shows the results. The criterion for cleanliness was expressed in 11 levels from 0 to 10 (best = 10).

Table 4 Results of low-temperature cleanliness evaluation Example 14 Imperial case 15 Difficult example 17 Comparative example 3 Ring sticking top 10 10 10 10 Ring sticking Second 10 10 10 10 Ring groove top Second 8.1 9.9 10 7.8 Ring land top 5.1 10 10 3.9 Ring land second 7.6 10 10 7.6 Biston skirt 7.6 10 10 7.5 Under crown 9.9 10 10 9.5 Total (up to 80 points) 6-5. 0 78. 8 79. 1 63. 3 Exhaust system obstruction evaluation test

JASOM 3 4 3 — 92, which is the standard of the Society of Automotive Engineers of Japan, was adopted as a test to evaluate the degree of output reduction due to the accumulation of power and carbon in the muffler. Examples 1, 14, 15 and 17 according to the present invention shown in Table 2 Lubricants for cycle engines, and Table 2 for comparison The mineral oil-based two-cycle engine lubricating oil of Comparative Example 1 and the low smoke type polybutene-based two-cycle engine of Comparative Example 3 shown in Figure 3 Using the lubricating oil for gin as a sample oil, an exhaust system clogging evaluation test was performed. The test method is specified in the JAS 0 standard, and the suction negative pressure is 2 k in the mode operation in which a generator is used and no load and a 75 W load are controlled by the exhaust gas temperature. It measures the time until it becomes Pa. Table 5 shows the results JASOM 3 4 3 — According to the way of organizing the test results specified in 92, the standard oil (JATRE-1) is expressed as a closure index with 100 as the standard oil. ing. The higher the index, the more difficult it is for the exhaust system to block. JATER-1 is selected to represent the performance of a low smoke type two-cycle engine lubricating oil and is based on this oil. The performance index required for low-smoke two-cycle engine lubricating oils with an index of 90 or more is specified in JAS0M345-93. Table 5 Exhaust system closing test results

The compositions of Examples 1 to 17 used the polyoxyalkylene glycol derivative constituting the present invention as a base oil, and had a two-cycle enzymatic composition. These are lubricating oils for diesel engines, but as is clear from the performance evaluation test results in Table 2, the smoke is significantly less than that of mineral oil (Comparative Example 1). Polybutene (Comparative Example 2) and a commercially available low smoke type 2 cycle enzymatic using polybutene as part of the base oil composition Lubricating oils for engines (Comparative Examples 3 and 4).

On the other hand, in engine startability, it is generally desired that the number of seconds is shorter than that of a mineral oil (Comparative Example 1). However, in Examples 1 to 17 according to the present invention, 2 Both mineral oils for cycle engines are mineral oils (Comparative Example 1) and commercially available lubricants for 2 cycle engines (Comparative Examples 3 and 4) Featuring fewer seconds and excellent startability. On the other hand, polybutene (Comparative Example 2) is inferior in engine startability due to the adhesiveness of polybutene.

In addition, it is clear from the results in Table 3 that the lubricating oil for 2 cycle engines containing the component Β (Examples 10 and 1) 1, 15 and 17) show superior high-temperature detergency compared to the two-cycle lubricating oil of Example 1 and show that component B The effect of the addition is clearly shown.

In addition, as can be seen from the results in Table 4, a lubricating oil for two-cycle engine containing the component (c) or (d) (Example 15) And 17) were superior to the lubricating oil for cycle 2 engine containing no component (c) or (d) (Example 14). It shows low-temperature detergency, and the effect of adding component (c) or (d) is clearly shown. Also, as is evident from the results in Table 5, the two-cycle engine lubricating oil of the present invention (Examples 1, 14, 15, and 17) Are compared with the conventional mineral oil-based two-cycle engine lubricant (Comparative Example 1) and the low smoke type two-cycle engine lubricant (Comparative Example 3). In comparison, it shows more than 3 times longer life for muffler clogging.

Industrial availability

As described above, the two-cycle engine lubricating oil of the present invention generates remarkably low exhaust smoke (smoke) and has a low engine start-up performance. Excellent, cleanliness that prevents carbon clogging of the exhaust system, excellent high-temperature and low-temperature cleanliness in the engine, and more It has excellent loadability.

Claims

The scope of the claims

) A two-cycle engine characterized in that a polyoxyalkylene glycol derivative represented by the general formula (1) is used as a base oil. Lubricating oil.

R ³ R ^s

R'- O— ^ C-C-O ^-R ² --(1)

R ⁶

(In the formula, R ¹ and R 2 may be the same or different, and may be hydrogen, an alkyl group having 122 carbon atoms, and an alkyl group having 122 carbon atoms, respectively.) Alkynyl group, Alkyl group with 520 carbon atoms, Alkyl group with Alkyl port, or Alkyl group with 620 carbon atoms, or Alkyl group with 620 carbon atoms R 3, R 4, R 5, and R 6 are the same or different, but are not the same as R 3, alkyl aryl, or aryl alkyl groups. R3, R4, R5, and R6, each of which is a hydrogen, methyl, or ethyl group. Is 1 or 2, and a is an integer of 1200.)) A. Polyoxyalkylenglycol represented by general formula (1) Base oil as the base oil,

R ³ R ⁵

R 0— C— C— 0— R ² ··· (1)

R ^A R ^G

(In the formula, R 1 and R 2 may be the same or different, and each is hydrogen, an alkyl group having 122 carbon atoms, Alkenyl group having 3 to 22 carbon atoms, Alkyl alkyl group having 5 to 20 carbon atoms or Alkyl Alkyl group having Alkyl mouth, Alkali group having carbon atom Are aryl groups, alkyl aryl groups or aryl alkyl groups of the formulas 6 to 20; R ³ , R ⁴ , R 5 and R 6 ^May be the same or different and are each a hydrogen, a methyl group or an ethyl group, and R 3, R 4, R ⁵ and The total carbon number of R ⁶ is 1 or 2, and a-is an integer of 1 to 200. )

B. At least one nitrogen-containing compound selected from the following (a) to (d):

(a) — a nitrogen-containing compound represented by the general formula (2).

_{_{H - N H - CNH - C}} ~ ^ 0- CH - CH- OR 7 - ... (2)

'' ^b II II

0 R ⁸ R ⁹

(In the formula, R 7 is an alkyl group having 1 to 22 carbon atoms, an alkylene group having 3 to 22 carbon atoms, or an alkyl group having 5 to 15 carbon atoms.) Or an alkyl cycloalkyl group, or an aryl group having 6 to 18 carbon atoms, or an alkyl aryl group.

— Indicates a radical or an arylalkyl group, and R ⁸ and R ⁹ may be the same or different, each being hydrogen or Alkyl group having 2 to 6 carbon atoms.

The total carbon number of R ⁸ and R ⁹ is 2 to 8, and b is 1 to

An integer of 8 and c is an integer between 5 and 40. )

(b) Borides of the nitrogen-containing compound of (a)

(c) a nitrogen-containing compound represented by the general formula (3) XY

Hl-[(-R10-NH-) _d . (-Rio-i-) _e ] i H... (3)

(In the formula, X represents an acyl group having 6 to 30 carbon atoms derived from a hydrogen atom or a fatty acid, and Y represents 6 to 30 carbon atoms derived from a fatty acid. Represents an acyl group; R io represents an alkylene group having 2 to 4 carbon atoms; d is an integer of 0 to 11; e is an integer of 0 to 11; ≤ d + e ^ 11 1. However, one molecule has at least one acyl group.)

(d) Borides of the nitrogen-containing compounds of (c)

A lubricating oil composition for two-cycle engines characterized by containing 0.5 to 30% by weight, based on the total amount of the composition. A. A polyoxyalkylene glycol derivative represented by the general formula (4) is used as a base oil,

R13R15

Rii— 0 ~ ft-C-O: ~ R12 (4)

16

(In the formula, R 1 1 your good beauty R 1 ² is rather good even though Tsu Do different even in the same, hydrogen, respectively Re its, A Le key Le group having 1 to 4 carbon atoms, have Ru Oh is § Li Lumpur group having 6 to 2 0, a Le key Le § Li Lumpur groups or the Ri Ah in § rie Le a Le key group, or R 1 1 and R 1 ² throat Chi et al On the other hand, or both of them are an aryl group, an alkyl aryl group or an aryl alkyl group having 6 to 20 carbon atoms. 1 ^ R 15 and R ₆ Rather good even if Tsu Do different even in the same, their Re, respectively hydrogen, was main Chi Le group or Ri Oh by E Ji group, or One _{R 1 3, R 4 n R} 5 your good beauty R (The total number of carbon atoms in ¹⁶ is 1 or 2, and f is an integer from 1 to 200.)

B. At least one nitrogen-containing compound selected from the following (c) and component (d):

(c) a nitrogen-containing compound represented by the general formula (3)

X Y

HN- [(-R1D-NH-) _d . (-R10-N-) _e ]-H... (3)

(In the formula, X represents an acyl group having 6 to 30 carbon atoms derived from a hydrogen atom or a fatty acid, and Y represents 6 to 30 carbon atoms derived from a fatty acid. And R io represents an alkylene group having 2 to 4 carbon atoms, d is an integer of 0 to 11 and e is an integer of 0 to 11; 2 ^ d + e ^ 11 1. However, one molecule has at least one acyl group.)

(d) Borides of the nitrogen-containing compounds of (c)

A lubricant composition for two-cycle engines, comprising 0.5 to 30% by weight based on the total amount of the composition. ) Mix two cycle oil lubricating oil based on the polyalkylene glycol derivative represented by the general formula (1) as a base oil. It is introduced into the two-cycle engine by the system or the separation system, and is characterized by lubricating the bearings and sliding parts in the engine. Equlen How to lubricate gin.

R ^{3 5}

R to 0 C-C-1 0 R ^2- (1)

R "R ⁶

(In the formula, R 1 and R 2 may be the same or different, and each may be hydrogen, an alkyl group having 1 to 22 carbon atoms, and 3 carbon atoms. Alkenyl group of ~ 22, Alkyl group of Alkyl port or Alkyl group of Alkyl port with 5 ~ 20 carbon atoms. Up to 20 aryl groups, alkyl aryl groups, or aryl alkyl groups, and R ³ , R 4, R 5, and R 6 are the same. rather good even if Tsu Do different even in one, each Re its Re hydrogen, was Demon Eyes Chi Le based on Ri Ah in E Chi group, or one R 3, R 4, R ₅ your good beauty R ₆ Is 1 or 2, and a is an integer of 1 to 200.)) A. Polyoxyalkyl represented by general formula (1) Lung glycol derivative as base oil,

R ³ R ⁵

_R i_ 0— ^ C-C-O ^-R ² --(1)

R ^c

(In the formula, R i and R 2 may be the same or different, each being hydrogen, an alkyl group having 1 to 22 carbon atoms, and a carbon number of 3 to 22 Alkynyl group, Alkyl alkyl group or Alkyl Alkyl group with 5 to 20 carbon atoms. ~ 20 free groups, alkyl groups A reel group or a real alkyl group, and R 3,

R ^{4 and} R ⁵ and R ⁶ may be the same or different, each being a hydrogen, a methyl or an ethyl group, and the R 3. R _T R 5 your good beauty was a total carbon number of force 1 or of R ₆ is Ri Ah in 2, a is Ru Oh 1 to 2 0 0 integer. ;)

(a) — a nitrogen-containing compound represented by the general formula (2).

H— ^ H- CzH, ^ — N H- C— ^ O-CH-CH -— OR ⁷ …-(2) • ^b II II

0 ⁸ R ^s

(In the formula, R 7 is an alkyl group having 1 to 22 carbon atoms, an alkylene group having 3 to 22 carbon atoms, and a cycloalkyl group having 5 to 15 carbon atoms. Or an alkylcycloalkyl group, an aryl group having 6 to 18 carbon atoms, an alkylaryl group or an aryl group. R ⁸ and R 9 may be the same or different, and each represents hydrogen or an alkyl having 2 to 6 carbon atoms. Ri Ah Le group, or one total number of carbon atoms in R s and R ₉ Ri Oh at 2 ~ 8, b is an integer of 1 ~ 8, c is Ru Ah in integer of 5-4 0.)

(b) Borides of the nitrogen-containing compound of (a)

(c) a nitrogen-containing compound represented by the general formula (3)

X Y

HN- [(-R1D-NH-) _d · (-R10-N-) _e ] — H · · · (3)

(Where X is derived from hydrogen atoms or fatty acids) Y represents an acyl group having 6 to 30 carbon atoms, Y represents an acyl group having 6 to 30 carbon atoms derived from a fatty acid, and R io represents an alkyl group having 2 to 4 carbon atoms. Represents a chiral group, d is an integer of 0 to 11, e is an integer of 0 to 11, and is 2 ^ d + e11. However, one molecule has at least one acyl group. )

(d) Borides of the nitrogen-containing compounds of (c)

A two-cycle engine lubricating oil composition containing 0.5 to 30% by weight based on the total amount of the composition, based on the mixing system or the separation system. A two-cycle engine lubrication method that is introduced into the engine to lubricate the bearings and sliding parts in the engine.

A. A polyoxyalkylene glycol derivative represented by the general formula (4) is used as a base oil,

Rii- 0 ~~ R12... (4)

(In the formula, R 1 1 your good beauty R ¹ 2 is Tsu Do different even in the same record, even rather good, each Re its Re hydrogen, A Le key Le group having 1 to 4 carbon atoms, Oh Ru have 6 to 2 0 of § Li Lumpur group carbons a Le key Le § Li was one Le group or the Ri Ah in § rie Le a Le key Le group, R 1 1 and R 1 ² throat Chi et al On the other hand, or both of them are a C 6 -C 20 aryl group, an alkyl aryl group or an aryl alkyl group. R 1 _N R 15 and R i ₆ Rather good even if Tsu Do different even in the same, each Re its Re hydrogen, was main Chi Le group or Ri Oh by E Ji group, or One ^{R 1 3, R 1 4,} R 1 5 Contact And the total number of carbon atoms of R 16 is 1 or 2, and f is an integer of 1 to 200.)

(c) a nitrogen-containing compound represented by the general formula (3)

X Y

HN- [(-R1D-NH-) _d · (-Rio-l-) _e ] —H · · · (3)

(In the formula, X represents a hydrogen atom or an acyl group having 6 to 30 carbon atoms derived from a fatty acid, and Y represents a C 6 to 30 carbon atom derived from a fatty acid. Represents an acyl group; R io represents an alkylene group having 2 to 4 carbon atoms; d is an integer of 0 to 11; e is an integer of 0 to 11; ^ d + e ≤ 11 1. However, one molecule has at least one acyl group.)

(d) Borides of the nitrogen-containing compounds of (c)

A two-cycle engine lubricating oil composition containing 0.5 to 30% by weight based on the total amount of the composition by a mixing method or a separation method. A two-cycle engine lubrication method characterized by being introduced into the engine and lubricating the bearings and sliding parts in the engine.