JP2872465B2 - Lubricating oil composition - Google Patents

Lubricating oil composition

Info

Publication number
JP2872465B2
JP2872465B2 JP3284083A JP28408391A JP2872465B2 JP 2872465 B2 JP2872465 B2 JP 2872465B2 JP 3284083 A JP3284083 A JP 3284083A JP 28408391 A JP28408391 A JP 28408391A JP 2872465 B2 JP2872465 B2 JP 2872465B2
Authority
JP
Japan
Prior art keywords
carbon atoms
ester
weight
composition
oil
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
JP3284083A
Other languages
Japanese (ja)
Other versions
JPH0598276A (en
Inventor
峰夫 加賀谷
光明 石丸
宏明 石井
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eneos Corp
Original Assignee
Nippon Oil Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Oil Corp filed Critical Nippon Oil Corp
Priority to JP3284083A priority Critical patent/JP2872465B2/en
Priority to CA002079512A priority patent/CA2079512A1/en
Priority to AT92309033T priority patent/ATE147096T1/en
Priority to EP92309033A priority patent/EP0535990B1/en
Priority to DE69216346T priority patent/DE69216346D1/en
Publication of JPH0598276A publication Critical patent/JPH0598276A/en
Application granted granted Critical
Publication of JP2872465B2 publication Critical patent/JP2872465B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/02—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a non-macromolecular organic compound
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C10M101/02—Petroleum fractions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/02—Well-defined hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/38—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
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    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16—Amides; Imides
    • C—CHEMISTRY; METALLURGY
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
    • C10M133/56—Amides; Imides
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    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
    • C10M145/12—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate monocarboxylic
    • C10M145/14—Acrylate; Methacrylate
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    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
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    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C10M159/22—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing phenol radicals
    • C—CHEMISTRY; METALLURGY
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    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
    • C—CHEMISTRY; METALLURGY
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    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C10M169/048—Mixtures of base-materials and additives the additives being a mixture of compounds of unknown or incompletely defined constitution, non-macromolecular and macromolecular compounds
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/0206—Well-defined aliphatic compounds used as base material
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
    • C10M2203/1025—Aliphatic fractions used as base material
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    • C10M2203/1065—Naphthenic fractions used as base material
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    • C10M2207/028—Overbased salts thereof
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    • C10M2207/301—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids used as base material
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    • C10M2207/302—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
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    • C10M2209/084—Acrylate; Methacrylate
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    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089—Overbased salts
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/64—Environmental friendly compositions
    • C—CHEMISTRY; METALLURGY
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    • C10N2040/02—Bearings
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    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C—CHEMISTRY; METALLURGY
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    • C10N2040/25—Internal-combustion engines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
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    • C10N2040/251—Alcohol fueled engines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
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    • C10N2040/255—Gasoline engines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
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    • C10N2040/255—Gasoline engines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B77/00—Component parts, details or accessories, not otherwise provided for
    • F02B77/04—Cleaning of, preventing corrosion or erosion in, or preventing unwanted deposits in, combustion engines

Abstract

The lubricating oil composition of the present invention comprising an ester mixture as the main ingredient consisting of (A) 60 - 95 % by weight of an ester of a hindered alcohol with a straight-chain saturated fatty acid having 8 - 12 carbon atoms, and (B) 5 - 40 % by weight of a complex ester of a hindered alcohol with a straight-chain saturated fatty acid having 8 - 12 carbon atoms and also with a dibasic acid having 2 - 50 carbon atoms, the composition having excellent performances such as biodegradability, high-temperature engine cleanliness, lubricity and piston seizure preventiveness which are conductive to environmental protection.

Description

【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION

【０００１】[0001]

【産業上の利用分野】本発明は潤滑油組成物に関し、詳
しくは環境保護に寄与できる、生分解性、高温清浄性お
よび焼き付き防止性に優れた２サイクルエンジン油組成
物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a lubricating oil composition, and more particularly to a two-stroke engine oil composition which can contribute to environmental protection and has excellent biodegradability, high-temperature detergency and anti-seizure properties.

【０００２】[0002]

【従来の技術】２サイクルエンジンにおいては、潤滑機
構上、排気ガスに同伴されて未燃焼のエンジン油が排出
されるため環境汚染が懸念されている。すなわち、河
川、湖水、海で使用される船外機では、水中に排気ガス
が排出されるため、未燃焼油による水質汚濁が問題にな
る。またチェインソーなど森林で使用される伐採機でも
河川汚染につながる。2. Description of the Related Art In a two-stroke engine, unburned engine oil is discharged accompanying exhaust gas on a lubrication mechanism, and there is a concern about environmental pollution. That is, in an outboard motor used in rivers, lakes, and seas, since exhaust gas is discharged into water, water pollution due to unburned oil becomes a problem. Logging machines used in forests, such as chainsaws, can also lead to river pollution.

【０００３】ヨーロッパでは環境保護の立場から、２サ
イクルエンジン油の生分解性に対する法律規定や規格化
に向けての活動が活発に続けられている。このため、生
分解性を有する２サイクルエンジン油の開発が行われお
り、オイルメーカー数社から既に販売されている。これ
らの油はいずれも基油としてエステル化合物（炭素数１
６〜１８の飽和および不飽和混合系脂肪酸エステル）と
鉱油系溶剤とからなり、添加剤としてはアミノアミド系
無灰分散剤が添加されている。[0003] In Europe, from the standpoint of environmental protection, activities for the legal provisions and standardization of the biodegradability of two-cycle engine oils have been actively continued. For this reason, biodegradable two-stroke engine oils have been developed and are already sold by several oil manufacturers. Each of these oils is used as a base oil as an ester compound (having 1 carbon atom).
6-18 saturated and unsaturated mixed fatty acid esters) and a mineral oil-based solvent, and an aminoamide-based ashless dispersant is added as an additive.

【０００４】これらの市販油は船外機用の性能規格であ
るＴＣ−ＷＩＩ（水冷エンジン）に合格しているが、最
近になって製造される船外機用高出力水冷エンジンや空
冷エンジンでは、潤滑油の熱安定性が不足することか
ら、リング膠着やピストン焼付を生じることが考えられ
る。[0004] These commercially available oils have passed TC-WII (water-cooled engine), which is a performance standard for outboard motors. However, recently manufactured high-output water-cooled engines and air-cooled engines for outboard motors have been used. Since the thermal stability of the lubricating oil is insufficient, ring sticking and piston seizure may occur.

【０００５】このため、より高い熱安定性、より優れた
潤滑性を有する生分解性のある潤滑油の出現が求められ
ている。For this reason, there is a demand for a biodegradable lubricating oil having higher thermal stability and better lubricity.

【０００６】[0006]

【発明が解決しようとする課題】本発明は、生分解性を
有し、高温清浄性、潤滑性および焼付防止性に優れた潤
滑油を提供することを目的とする。SUMMARY OF THE INVENTION An object of the present invention is to provide a lubricating oil which has biodegradability and is excellent in high-temperature detergency, lubricity and anti-seizure properties.

【０００７】[0007]

【課題を解決するための手段】本発明者らは、上記の課
題に鑑み、さらに研究を重ねた結果、特定のエステルを
主成分とする潤滑油が上記の条件を満足することを見い
だし、本発明を完成するに至った。Means for Solving the Problems In view of the above problems, the present inventors have further studied and found that a lubricating oil containing a specific ester as a main component satisfies the above conditions. The invention has been completed.

【０００８】 すなわち、本発明の特定発明は、（Ａ）
ヒンダードアルコールと炭素数８〜１２の直鎖飽和脂肪
酸とのエステル６０〜９５重量％、および（Ｂ）ヒンダ
ードアルコールと炭素数８〜１２の直鎖飽和脂肪酸およ
び炭素数２〜５０の二塩基酸とのエステル５〜４０重量
％よりなるエステル混合物を主成分とし、ＭＩＴＩ法に
よる生分解性が３５％以上であることを特徴とする２サ
イクルエンジン油組成物を提供するものである。That is, the specific invention of the present invention relates to (A)
60 to 95% by weight of an ester of hindered alcohol and a linear saturated fatty acid having 8 to 12 carbon atoms, and (B) a hindered alcohol, a linear saturated fatty acid having 8 to 12 carbon atoms and a dibasic having 2 to 50 carbon atoms ester 5-40 consisting wt% ester mixture with an acid as a main component, the MITI method
2 Sa biodegradable according to characterized in that 35% or more
The present invention provides an engine oil composition.

【０００９】 また、本発明の第２発明は、（Ｉ）
（Ａ）ヒンダードアルコールと炭素数８〜１２の直鎖飽
和脂肪酸とのエステル６０〜９５重量％、および（Ｂ）
ヒンダードアルコールと炭素数８〜１２の直鎖飽和脂肪
酸および炭素数２〜５０の二塩基酸とのエステル５〜４
０重量％よりなるエステル混合物１００重量部に対し、
（ＩＩ）炭化水素系溶剤および／または潤滑基油３０重
量部以下を含有し、ＭＩＴＩ法による生分解性が３５％
以上であることを特徴とする２サイクルエンジン油組成
物を提供するものである。The second invention of the present invention provides (I)
(A) 60 to 95% by weight of an ester of a hindered alcohol and a linear saturated fatty acid having 8 to 12 carbon atoms, and (B)
Esters of hindered alcohol with straight-chain saturated fatty acids having 8 to 12 carbon atoms and dibasic acids having 2 to 50 carbon atoms
For 100 parts by weight of the ester mixture consisting of 0% by weight,
(II) containing 30 parts by weight or less of a hydrocarbon solvent and / or a lubricating base oil, and having a biodegradability of 35% by MITI method
The present invention provides a two-stroke engine oil composition characterized by the above.

【００１０】以下、本発明の内容をより詳細に説明す
る。本発明において、主成分として使用するエステル混
合物は、（Ａ）ヒンダードアルコールと炭素数８〜１２
の直鎖飽和脂肪酸とのエステル、および（Ｂ）ヒンダー
ドアルコールと炭素数８〜１２の直鎖飽和脂肪酸および
炭素数２〜５０の二塩基酸とのエステルの混合物であ
る。Hereinafter, the contents of the present invention will be described in more detail. In the present invention, the ester mixture used as the main component comprises (A) a hindered alcohol and 8 to 12 carbon atoms.
And a mixture of (B) an ester of a hindered alcohol with a straight-chain saturated fatty acid having 8 to 12 carbon atoms and a dibasic acid having 2 to 50 carbon atoms.

【００１１】この（Ａ）成分において、ヒンダードアル
コールとは、水酸基のβ炭素原子が第４級であるものを
意味する。具体的には、炭素数５〜１０の２〜４価のも
の、あるいはこれらの２〜３量体が好ましく使用され、
例えば、ネオペンチルグリコール、２−メチル−２−プ
ロピル−１，３−プロパンジオール、トリメチロールエ
タン、トリメチロールプロパン（ＴＭＰ）、トリメチロ
ールブタン、ペンタエリスリト−ル（ＰＥＴ）、ジ−
（トリメチロールプロパン）、トリ−（トリメチロール
プロパン）、ジ−（ペンタエリスリトール）、トリ−
（ペンタエリスリト−ル）などが挙げられる。また、炭
素数８〜１２の直鎖飽和脂肪酸としては、具体的には例
えば、カプリル酸、ペラルゴン酸、カプリン酸、ラウリ
ン酸などが使用できる。なお、脂肪酸は、酸無水物、酸
ハライド、金属塩などの誘導体の形で使用してもよい。
（Ａ）成分においては、これらの脂肪酸のうち異なった
２種以上のものが同一のヒンダードアルコールにエステ
ル化していてもよく、また、エステル化されないで残っ
ている水酸基を有していてもよい。In the component (A), the term "hindered alcohol" means that the β-carbon atom of the hydroxyl group is quaternary. Specifically, divalent or tetravalent ones having 5 to 10 carbon atoms or dimers or trimers thereof are preferably used,
For example, neopentyl glycol, 2-methyl-2-propyl-1,3-propanediol, trimethylolethane, trimethylolpropane (TMP), trimethylolbutane, pentaerythritol (PET), di-
(Trimethylolpropane), tri- (trimethylolpropane), di- (pentaerythritol), tri-
(Pentaerythritol) and the like. Further, as the straight-chain saturated fatty acid having 8 to 12 carbon atoms, specifically, for example, caprylic acid, pelargonic acid, capric acid, lauric acid and the like can be used. The fatty acids may be used in the form of derivatives such as acid anhydrides, acid halides, metal salts and the like.
In the component (A), two or more different fatty acids among these fatty acids may be esterified to the same hindered alcohol, or may have a remaining hydroxyl group without being esterified. .

【００１２】また、（Ｂ）成分において、ヒンダードア
ルコールおよび炭素数８〜１２の飽和脂肪酸としては、
上記（Ａ）成分と同様のものが用いられる。炭素数２〜
５０の二塩基酸としては、具体的には例えば、シュウ
酸、マロン酸、コハク酸、グルタル酸、アジピン酸、ピ
メリン酸、スベリン酸、アゼライン酸、セバシン酸、そ
の他さらに炭素数の多い酸などが使用できる。好ましく
は炭素数６〜４０のものが用いられる。In the component (B), the hindered alcohol and the saturated fatty acid having 8 to 12 carbon atoms include:
The same component as the component (A) is used. 2 carbon atoms
Specific examples of the 50 dibasic acids include, for example, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and other acids having more carbon atoms. Can be used. Preferably those having 6 to 40 carbon atoms are used.

【００１３】この（Ｂ）成分としては、例えば、一般式As the component (B), for example, a general formula

【００１４】[0014]

【化１】 Embedded image

【００１５】で表されるコンプレックスエステルを挙げ
ることができる。なお、式中、Ｘ1〜Ｘ4は同一でも異な
っていてもよく、それぞれ炭素数１〜４のアルキル基、
または一般式−ＣＨ2−ＯＣＯ−Ｒ4で表される基を示
す。また、Ｒ1は炭素数１〜４８のアルキレン基または
アルケニレン基を示す（但し、二塩基酸の炭素数が２の
ときはＲ1は存在しない）。Ｒ2〜Ｒ4は同一でも異なっ
ていてもよく、それぞれ炭素数７〜１１の直鎖アルキル
基を示す。ここで、Ｒ1は炭素数３〜５０の二塩基酸の
アルキレン基に、Ｒ2〜Ｒ4は炭素数８〜１２の直鎖飽和
脂肪酸のアルキル基にそれぞれ対応するものである。The complex ester represented by the following formula: In the formula, X 1 to X 4 may be the same or different and each have an alkyl group having 1 to 4 carbon atoms,
Or a group represented by the formula -CH 2 -OCO-R 4. R 1 represents an alkylene group or alkenylene group having 1 to 48 carbon atoms (however, when the dibasic acid has 2 carbon atoms, R 1 does not exist). R 2 to R 4 may be the same or different and each represents a straight-chain alkyl group having 7 to 11 carbon atoms. Here, R 1 corresponds to an alkylene group of a dibasic acid having 3 to 50 carbon atoms, and R 2 to R 4 correspond to an alkyl group of a linear saturated fatty acid having 8 to 12 carbon atoms.

【００１６】本発明においては、上記（Ａ）成分の含有
量は、基油全量基準で６０〜９５重量％、好ましくは７
０〜９０重量％であり、（Ｂ）成分の含有量は基油全量
基準で５〜４０重量％、好ましくは１０〜３０重量％で
ある。この範囲を満たさないときは組成物の粘度が適当
でなく、また（Ｂ）成分が４０重量％を超える場合には
生分解性が落ちるため好ましくない。なお、組成物の好
ましい動粘度は６〜１５ｍｍ2／ｓ、＠１００℃であ
る。In the present invention, the content of the component (A) is 60 to 95% by weight, preferably 7 to 95% by weight based on the total amount of the base oil.
The content of the component (B) is 5 to 40% by weight, preferably 10 to 30% by weight, based on the total amount of the base oil. If this range is not satisfied, the viscosity of the composition is not appropriate, and if the component (B) exceeds 40% by weight, the biodegradability is undesirably reduced. In addition, the preferable kinematic viscosity of the composition is 6 to 15 mm 2 / s, @ 100 ° C.

【００１７】本発明の潤滑油組成物においては、上記エ
ステル混合物を単独で用いてもよいが、必要に応じて炭
化水素系溶剤および／または潤滑基油が含有されていて
もよい。この炭化水素系溶剤としては、通常２サイクル
エンジン油に用いられるものでよく、例えば常圧におけ
る沸点が１５０〜３００℃の石油系および／または合成
系炭化水素溶剤が使用される。具体的には、ストッダー
ドソルベント、ミネラルスピリット、灯油留分、ノルマ
ルパラフィン、イソパラフィン、プロピレンオリゴマー
などが用いられる。潤滑基油としては、通常潤滑油の基
油として使用されているものでよく、例えば原油を常圧
蒸留および減圧蒸留して得られた潤滑油留分を精製して
得られたパラフィン系、ナフテン系の鉱油、ポリ−α−
オレフィン（１−オクテンオリゴマ−、１−デセンオリ
ゴマーなど）、ポリブテン、アルキルベンゼン、アルキ
ルナフタレン、ポリグリコール、ジエステル（ジトリデ
シルグルタレート、ジ２−エチルヘキシルアジペート、
ジイソデシルアジペート、ジトリデシルアジペート、ジ
２−エチルヘキシルセバケートなど）、脂肪酸の炭素数
が直鎖でかつ７以下または１３以上、あるいは分岐のポ
リオールエステル（トリメチロールプロパンステアレー
ト、トリメチロールプロパンオレエート、ペンタエリス
リト−ル２−エチルヘキサノエ−トなど）、ポリフェニ
ルエ−テル、フッ素系油、シリコン系油などが使用でき
る。In the lubricating oil composition of the present invention, the above ester mixture may be used alone, but may contain a hydrocarbon solvent and / or a lubricating base oil as required. The hydrocarbon-based solvent may be one usually used for two-cycle engine oil, and for example, a petroleum-based and / or synthetic hydrocarbon solvent having a boiling point at normal pressure of 150 to 300 ° C is used. Specifically, Stoddard solvent, mineral spirit, kerosene fraction, normal paraffin, isoparaffin, propylene oligomer and the like are used. The lubricating base oil may be any of those usually used as lubricating base oils, for example, paraffinic and naphthenic oils obtained by refining a lubricating oil fraction obtained by distilling crude oil under normal pressure and reduced pressure. Mineral oil, poly-α-
Olefin (1-octene oligomer, 1-decene oligomer, etc.), polybutene, alkylbenzene, alkylnaphthalene, polyglycol, diester (ditridecyl glutarate, di-2-ethylhexyl adipate,
Diisodecyl adipate, ditridecyl adipate, di-2-ethylhexyl sebacate, etc.), linear or less fatty acid having 7 or less or 13 or more, or branched polyol esters (trimethylolpropane stearate, trimethylolpropane oleate, pentane) Erythritol 2-ethylhexanoate), polyphenyl ether, fluorine-based oil, silicon-based oil, and the like can be used.

【００１８】溶剤および／または上記エステル混合物以
外の潤滑基油を含有せしめる場合は、本発明の特徴であ
る優れた熱安定性や潤滑性、さらには生分解性を損なわ
ないために、上記エステル混合物よりなる基油１００重
量部に対して３０重量部以下、好ましくは２０重量部以
下であるのが望ましい。When a solvent and / or a lubricating base oil other than the above-mentioned ester mixture is contained, the above-mentioned ester mixture is used in order not to impair the excellent thermal stability and lubricity, and furthermore, the biodegradability characteristic of the present invention. It is desirably 30 parts by weight or less, preferably 20 parts by weight or less, based on 100 parts by weight of the base oil.

【００１９】さらに、本発明の組成物においては、その
性能をさらに向上させる目的で、必要に応じて公知の各
種添加剤を使用することができる。この添加剤としては
例えば、塩基性カルシウムスルホネート、塩基性カルシ
ウムフェネート、塩基性カルシウムサリシレート、アル
ケニルコハク酸イミド、ベンジルアミン、ポリアルケニ
ルアミンなどの清浄剤、ポリメタクリレートなどの流動
点降下剤、その他さび止め剤、消泡剤などが挙げられ
る。Further, in the composition of the present invention, various known additives can be used as needed for the purpose of further improving the performance. Such additives include, for example, basic calcium sulfonate, basic calcium phenate, basic calcium salicylate, alkenyl succinimide, benzylamine, detergents such as polyalkenylamine, pour point depressants such as polymethacrylate, and other rusts. Stoppers, defoamers and the like.

【００２０】これら添加剤は単独で添加してもよく、ま
た数種類併用して添加してもよい。添加量も任意である
が、通常、個々の添加量は基油１００重量部に対して３
０重量部以下、好ましくは０．５〜１５重量部である。These additives may be added alone or in combination of several kinds. The addition amount is also optional, but usually, the addition amount is 3 parts per 100 parts by weight of the base oil.
0 parts by weight or less, preferably 0.5 to 15 parts by weight.

【００２１】 本発明の潤滑油組成物は、生分解性に優
れていることから、特に船外機用、チェインソーなどの
２サイクルエンジンに適しているが、その他、モペッ
ト、モーターサイクルなどの２輪車用エンジン、芝刈
機、発電機などの汎用エンジンなどにも好ましく用いら
れる。 Since the lubricating oil composition of the present invention is excellent in biodegradability, it is particularly suitable for two-stroke engines such as for outboard motors and chain saws. wheel vehicles engines, lawn mowers, Re preferably used et <br/> that in general-purpose engines, such as an electrical generator.

【００２２】[0022]

【実施例】以下、本発明の内容を、実施例および比較例
によりさらに具体的に説明するが、本発明は、これらに
何等限定されるものではない。EXAMPLES Hereinafter, 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 thereto.

【００２３】＜１．生分解性および熱安定性＞本発明の
基本的な性能である生分解性と熱安定性について評価し
た。<1. Biodegradability and Thermal Stability> Biodegradability and thermal stability, which are basic performances of the present invention, were evaluated.

【００２４】（１）生分解性 クーロメーター法（閉鎖系酸素消費測定装置、通常化審
法のうちのＭＩＴＩ法と呼ばれている）で行った。この
方法は培養温度が２５℃で培養期間が１４日間の試験で
ある。分解度は、 分解度＝［（ＢＯＤ−Ｂ）／ＴＯＤ］×１００ ＢＯＤ：供試物質の生物学的酸素要求量（測定値）ｍｇ Ｂ：基礎培養基に活性汚泥を接種したものの酸素消費量
（測定値）ｍｇ ＴＯＤ：供試物質が完全に酸化された場合に必要とされ
る理論的酸素要求量（計算値）ｍｇ で求められる。またＴＯＤは供試油の元素分析値から分
子式を計算して求めた。(1) Biodegradability The biodegradability was measured by a coulometer method (closed oxygen consumption measuring device, usually called MITI method of the Chemical Substances Control Law). This method is a test in which the culture temperature is 25 ° C. and the culture period is 14 days. Degradation degree is as follows: Degradation degree = [(BOD-B) / TOD] × 100 BOD: Biological oxygen demand (measured value) of test substance mg B: Oxygen consumption of basic culture inoculated with activated sludge ( (Measured value) mg TOD: The theoretical oxygen demand (calculated value) mg required when the test substance is completely oxidized. TOD was determined by calculating the molecular formula from the elemental analysis value of the test oil.

【００２５】この試験に基づいて分解度が３５〜４０％
を示す供試物質は、ほとんど生分解されるものと考えら
れており、本発明の組成物の生分解性基準もこの値に準
じた。Based on this test, the degree of decomposition is 35-40%
Is considered to be almost biodegradable, and the biodegradability criterion of the composition of the present invention was also in accordance with this value.

【００２６】（２）熱安定性 ホットチューブ試験（ＨＴＴ）で評価した（日石レビュ
ー３１巻、５号、２２９ページ（１９８９年））。これ
はガラスチューブを電気炉内に差し込み、油を空気で押
し上げる装置である。油はガラスチューブ内を通る際に
熱および酸化を受け劣化する。ガラス内壁に付着したラ
ッカー色の程度を付着物なしが１０点、黒色が０点とし
たメリット評点で表す。エンジン試験によるピストン清
浄性とＨＴＴ評点には比較的良い相関性があるため、Ｈ
ＴＴはエンジン試験にかける前のスクリーニング試験と
して活用されている。本発明の組成物においては、ＨＴ
Ｔ評点は５点以上を基準とした。結果を表１に示す。(2) Thermal stability Evaluation was made by a hot tube test (HTT) (Nisseki Review Vol. 31, No. 5, page 229, 1989). This is a device that inserts a glass tube into an electric furnace and pushes up oil with air. Oil degrades due to heat and oxidation when passing through the glass tube. The degree of the lacquer color adhering to the inner wall of the glass is represented by a merit score of 10 points for no adhering matter and 0 points for black. Since there is a relatively good correlation between the piston cleanliness from the engine test and the HTT score,
TT is used as a screening test before an engine test. In the composition of the present invention, HT
The T score was based on 5 or more points. Table 1 shows the results.

【００２７】[0027]

【表１】 [Table 1]

【００２８】実施例１〜６は本発明の組成物であり、比
較例の組成物に比べ、生分解性および熱安定性で優れた
性能を発揮する。Examples 1 to 6 are compositions of the present invention, and exhibit excellent performance in biodegradability and thermal stability as compared with the compositions of Comparative Examples.

【００２９】（１）比較例１は、炭素数が１８の脂肪酸
（オレイン酸）を主体にするＴＭＰエステルである。本
発明の組成物と比べ、生分解性はあるものの、熱安定性
が劣っている。(1) Comparative Example 1 is a TMP ester mainly composed of a fatty acid having 18 carbon atoms (oleic acid). Compared to the composition of the present invention, it has biodegradability, but is inferior in heat stability.

【００３０】（２）比較例２は、炭素数が８の分岐構造
の脂肪酸からなるＰＥＴエステルである。熱安定性は良
いものの、生分解性が低い。(2) Comparative Example 2 is a PET ester comprising a branched fatty acid having 8 carbon atoms. Good thermal stability but low biodegradability.

【００３１】（３）比較例３および比較例４は、いずれ
も本発明の組成物を構成する（Ａ）成分のみの使用であ
り、生分解性、熱安定性とも良い結果を示す。しかし、
各々単独では動粘度が６ｍｍ2／ｓ、＠１００℃未満で
あり、２サイクルエンジン油基油としては粘度が低す
ぎ、潤滑性や焼き付き性が懸念される。また比較例５
は、本発明の組成物を構成する（Ｂ）成分のみの使用で
あるが、比較例３および４とは逆に動粘度が３０ｍｍ2
／ｓ、＠１００℃を超えており、単独では清浄性、流動
性で問題がある。(3) Comparative Examples 3 and 4 each use only the component (A) constituting the composition of the present invention, and show good results in both biodegradability and thermal stability. But,
Each of them has a kinematic viscosity of 6 mm 2 / s and less than ＠ 100 ° C., and the viscosity is too low for a two-cycle engine oil base oil, which may cause lubricity and seizure. Comparative Example 5
Is the use of only the component (B) which constitutes the composition of the present invention, but the kinematic viscosity is 30 mm 2, contrary to Comparative Examples 3 and 4.
/ S, which exceeds ℃ 100 ° C., and there is a problem in cleanliness and fluidity by itself.

【００３２】（４）比較例６は本発明の組成物を構成す
る（Ａ）成分および（Ｂ）成分を使用しているが、混合
割合が本発明の組成物の範囲を逸脱するため、生分解性
が悪くなる。(4) In Comparative Example 6, the components (A) and (B) constituting the composition of the present invention were used. However, since the mixing ratio was outside the range of the composition of the present invention, Degradability deteriorates.

【００３３】（５）比較例７および比較例８は市販の生
分解性２サイクルエンジン油である。これらは基油の主
成分に比較例１のエステルを用いている。これらに比
べ、本発明の組成物である実施例１〜６は熱安定性が著
しく改善されていることが明らかである。また比較例９
はポリブテン基油の市販低排気煙型２サイクルエンジン
油であるが、熱安定性は良いものの、生分解性が低い。
また比較例１０は鉱油系基油の２サイクルエンジン油、
比較例１１は基油の一部がポリブテン基油の市販低排気
煙型２サイクルエンジン油であるが、熱安定性および生
分解性とも低い。(5) Comparative Examples 7 and 8 are commercially available biodegradable two-cycle engine oils. These use the ester of Comparative Example 1 as the main component of the base oil. In comparison with these, it is clear that the compositions of the present invention, Examples 1 to 6, have significantly improved thermal stability. Comparative Example 9
Is a commercially available low-emission smoke type two-stroke engine oil of polybutene base oil, which has good thermal stability but low biodegradability.
Comparative Example 10 is a two-stroke engine oil of a mineral base oil,
Comparative Example 11 is a commercially available low-emission smoke type two-cycle engine oil in which a part of the base oil is a polybutene base oil, but also has low heat stability and low biodegradability.

【００３４】（６）実施例に示すように、本発明の組成
物は（Ａ）成分と（Ｂ）成分を特定量併用することで、
２サイクルエンジン油に要求される適当な範囲の粘度特
性を有し、優れた潤滑性を付与し、さらには本発明の重
要な特性である生分解性と熱安定性について、同時に優
れた性能を満足させるものである。(6) As shown in the examples, the composition of the present invention is obtained by using the components (A) and (B) in a specific amount.
It has viscosity characteristics in the appropriate range required for two-stroke engine oils, imparts excellent lubricity, and at the same time, has excellent performance for biodegradability and thermal stability, which are important characteristics of the present invention. It will satisfy you.

【００３５】＜２．エンジン試験結果＞ （１）モーターサイクルエンジンによる高温清浄性試験 排気量１２３ｃｃ単気筒のモーターサイクル用空冷２サ
イクルエンジンを用い、エンジン回転数７０００ｒｐ
ｍ、全負荷、プラグ座温２６０℃、燃料：油混合比２
０：１、３ｈｒｓの試験を行った<2. Engine Test Results> (1) High-temperature cleanliness test using a motorcycle engine Using an air-cooled two-cycle engine for motorcycles with a displacement of 123 cc and a single cylinder, the engine speed was 7000 rpm
m, full load, plug seat temperature 260 ° C, fuel: oil mixing ratio 2
0: 1, 3 hrs test

【００３６】結果を表２に示すが、実施例３の本発明の
組成物は市販生分解性２サイクルエンジン油である比較
例７および比較例８と比べ、ピストンとシリンダ間の耐
焼き付き性に優れ、試験後のピストンにもリング膠着が
なく、ピストン清浄性が極めて優れていた。The results are shown in Table 2. The composition of the present invention of Example 3 is superior to Comparative Examples 7 and 8 which are commercially available biodegradable two-cycle engine oils in the seizure resistance between the piston and the cylinder. Excellent, there was no ring sticking on the piston after the test, and the piston cleanliness was extremely excellent.

【００３７】[0037]

【表２】 [Table 2]

【００３８】（２）発電機用エンジンによる清浄性試験 排気量６３ｃｃ単気筒の発電機用エンジンを用い、全負
荷（８００Ｗ）運転で５ｈｒｓ試験した。プラグ座温
は、発電機に装備されている強制冷却ファンの空気吸入
口を約５０％カバーすることで、２００℃に設定した。
燃料：油混合比は５０：１（混合潤滑）で行った。(2) Cleanliness Test Using a Generator Engine A 5 hrs test was conducted at a full load (800 W) using a 63 cc single cylinder generator engine. The plug seat temperature was set to 200 ° C. by covering about 50% of the air inlet of the forced cooling fan provided in the generator.
The fuel: oil mixing ratio was 50: 1 (mixed lubrication).

【００３９】結果を表３に示すが、実施例４の本発明の
組成物は、市販生分解性２サイクルエンジン油である比
較例７、また鉱油系２サイクルエンジン油である比較例
１０に比べ、リング膠着がなく、ピストン清浄性が優れ
ており、シリンダヘッドデボジットが極めて少なかっ
た。The results are shown in Table 3. The composition of the present invention in Example 4 was compared with Comparative Example 7 which was a commercially available biodegradable two-cycle engine oil and Comparative Example 10 which was a mineral oil-based two-cycle engine oil. No ring sticking, excellent piston cleanliness, and extremely low cylinder head devodge.

【００４０】[0040]

【表３】 [Table 3]

【００４１】（３）チェーンソーエンジンによる清浄性
試験 排気量４５ｃｃ単気筒のチェーンソーエンジンを用い、
エンジン回転数９０００ｒｐｍ、全負荷、プラグ座温２
８０℃、燃料：油混合比５０：１（混合潤滑）、３０ｈ
ｒｓの試験を行った。(3) Cleanliness test using a chainsaw engine Using a chainsaw engine with a displacement of 45 cc and a single cylinder,
Engine speed 9000 rpm, full load, plug seat temperature 2
80 ° C, fuel: oil mixing ratio 50: 1 (mixed lubrication), 30h
The rs test was performed.

【００４２】結果を表４に示すが、実施例４の本発明の
組成物は市販の低煙型２サイクルエンジン油である比較
例１１と比べ、耐リング膠着性に優れ、ピストン清浄性
が格段に優れていた。The results are shown in Table 4. The composition of the present invention of Example 4 is superior to Comparative Example 11 which is a commercially available low-smoke type two-stroke engine oil in ring-sticking resistance and significantly improved piston cleanliness. Was excellent.

【００４３】[0043]

【表４】 [Table 4]

【００４４】以上のように、本発明の組成物の性能に優
れている点を幾つか例示したが、この他のエンジン試験
においても同様な結果であった。また本発明の組成物は
船外機用２サイクルエンジン油のＮＭＭＡ（Ｎａｔｉｏ
ｎａｌ Ｍａｒｉｎｅ Ｍａｎｕｆａｃｔｕｒｅｒｓ
Ａｓｓｏｃｉａｔｉｏｎ）規格であるＴＣ−ＷＩＩに合
格しており、また船外機用２サイクルエンジン油の生分
解性を評価する試験法であるＣＥＣ Ｌ−３３−Ｔ−８
２（日本のＭＩＴＩ法と生分解性試験の方法が異なる）
において、生分解性の基準である６７％以上に合格した
（例えば比較例７が分解度６７％に対し、実施例４では
分解度８７％を示した）。As described above, some of the points of excellent performance of the composition of the present invention have been exemplified, but similar results were obtained in other engine tests. Further, the composition of the present invention is a two-stroke engine oil for an outboard motor, NMMA (Natio
nal Marine Manufacturers
CEC L-33-T-8, a test method for evaluating the biodegradability of two-stroke engine oil for outboard motors
2 (The biodegradability test method differs from the Japanese MITI method)
, Passed the biodegradability criterion of 67% or more (for example, Comparative Example 7 showed a degree of degradation of 67%, while Example 4 showed a degree of degradation of 87%).

【００４５】[0045]

【発明の効果】以上のように、本発明の組成物は、市場
で問題となっているピストンリング膠着やピストン焼付
に対する問題点を解決する潤滑油である。As described above, the composition of the present invention is a lubricating oil which solves the problems of piston ring sticking and piston seizure which are problems in the market.

───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｃ１０Ｎ 40:26 (58)調査した分野(Int.Cl.6，ＤＢ名) C10M 105/38 C10M 105/42 C10N 40:25 C10N 40:26 ──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. 6 identification code FI C10N 40:26 (58) Investigated field (Int.Cl. 6 , DB name) C10M 105/38 C10M 105/42 C10N 40:25 C10N 40:26

Claims (3)

(57)【特許請求の範囲】(57) [Claims] 【請求項１】 （Ａ）ヒンダードアルコールと炭素数８
〜１２の直鎖飽和脂肪酸とのエステル６０〜９５重量
％、および （Ｂ）ヒンダードアルコールと炭素数８〜１２の直鎖飽
和脂肪酸および炭素数２〜５０の二塩基酸とのエステル
５〜４０重量％、 よりなるエステル混合物を主成分とし、ＭＩＴＩ法によ
る生分解性が３５％以上であることを特徴とする２サイ
クルエンジン油組成物。1. A hindered alcohol having 8 carbon atoms
(B) an ester of a hindered alcohol with a straight-chain saturated fatty acid having 8 to 12 carbon atoms and a dibasic acid having 2 to 50 carbon atoms; wt%, the main component become more ester mixture, the MITI method
2 Sai biodegradable that is characterized in that 35% or more
Kle engine oil composition. 【請求項２】 （Ｉ）（Ａ）ヒンダードアルコールと炭
素数８〜１２の直鎖飽和脂肪酸とのエステル６０〜９５
重量％、および （Ｂ）ヒンダードアルコールと炭素数８〜１２の直鎖飽
和脂肪酸および炭素数２〜５０の二塩基酸とのエステル
５〜４０重量％、 よりなるエステル混合物１００重量部に対し、 （ＩＩ）炭化水素系溶剤および／または潤滑基油３０重
量部以下を含有し、ＭＩＴＩ法による生分解性が３５％
以上であることを特徴とする２サイクルエンジン油組成
物。2. (I) Ester 60-95 of (A) hindered alcohol with a straight-chain saturated fatty acid having 8 to 12 carbon atoms.
(B) 5 to 40% by weight of an ester of a hindered alcohol, a straight-chain saturated fatty acid having 8 to 12 carbon atoms and a dibasic acid having 2 to 50 carbon atoms, (II) containing 30 parts by weight or less of a hydrocarbon solvent and / or a lubricating base oil, and having a biodegradability of 35% by MITI method
A two-cycle engine oil composition characterized by the above . 【請求項３】 前記エステル混合物１００重量部に対
し、無灰分散剤５〜２５重量部を更に含有することを特
徴とする請求項１または２記載の２サイクルエンジン油
組成物。 3. An amount of 100 parts by weight of the ester mixture.
And further contains 5 to 25 parts by weight of an ashless dispersant.
The two-stroke engine oil according to claim 1 or 2, characterized in that:
Composition.
JP3284083A 1991-10-04 1991-10-04 Lubricating oil composition Expired - Lifetime JP2872465B2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP3284083A JP2872465B2 (en) 1991-10-04 1991-10-04 Lubricating oil composition
CA002079512A CA2079512A1 (en) 1991-10-04 1992-09-30 Lubricating oil composition
AT92309033T ATE147096T1 (en) 1991-10-04 1992-10-02 LUBRICANT OIL COMPOSITION
EP92309033A EP0535990B1 (en) 1991-10-04 1992-10-02 A lubricating oil composition
DE69216346T DE69216346D1 (en) 1991-10-04 1992-10-02 Lubricating oil composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP3284083A JP2872465B2 (en) 1991-10-04 1991-10-04 Lubricating oil composition

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JPH0598276A JPH0598276A (en) 1993-04-20
JP2872465B2 true JP2872465B2 (en) 1999-03-17

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AT (1) ATE147096T1 (en)
CA (1) CA2079512A1 (en)
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JPH05331481A (en) * 1992-05-29 1993-12-14 Tonen Corp Lubricant composition for two-cycle engine
DE4217961A1 (en) * 1992-05-30 1993-12-02 Fuchs Petrolub Ag Oel & Chemie Environmentally compatible and quickly biodegradable supplies for the circulation lubrication of engines and other units in vehicles and work machines
AU674024B2 (en) * 1992-08-28 1996-12-05 Henkel Corporation Biodegradable two-cycle engine oil compositions and ester base stocks
DE4313948A1 (en) * 1993-04-28 1994-11-03 Henkel Kgaa Hydraulic oils with improved seal compatibility
JPH07109477A (en) * 1993-10-15 1995-04-25 Oronaito Japan Kk Lubricating hydraulic oil common to agricultural equipment and civil engineering and building equipment
AU1437395A (en) * 1993-12-30 1995-07-17 Exxon Chemical Patents Inc. Biodegradable two-cycle oil composition
WO1996017907A1 (en) * 1994-12-08 1996-06-13 Exxon Chemical Patents Inc. Biodegradable branched synthetic ester base stocks and lubricants formed therefrom
JP2003522204A (en) * 1997-10-01 2003-07-22 ユニケマ ケミー ベスローテン フェンノートシャップ Complex esters, formulations containing these esters and their use
JP2000044972A (en) * 1998-08-03 2000-02-15 General Sekiyu Kk Method for improving biodegradability of lubricant, biodegradability improver, and biodegradable lubricant composition
FR2792325B1 (en) * 1999-06-30 2006-07-14 Renault NON-TOXIC AND BIODEGRADABLE FUNCTIONAL FLUIDS BASED ON NEOPOLYOL FAT CHAIN ESTERS FOR MOTOR VEHICLES
WO2005077876A1 (en) 2004-01-28 2005-08-25 Idemitsu Kosan Co., Ltd. Carbonyl compound containing long-chain branched alkyl group
JP5827782B2 (en) * 2009-05-08 2015-12-02 出光興産株式会社 Biodegradable lubricating oil composition

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US3505230A (en) * 1967-03-29 1970-04-07 Monsanto Co Functional ester base fluids containing corrosion inhibitors
FR2144559B1 (en) * 1971-07-05 1974-09-06 Inst Francais Du Petrole
FR2311088A1 (en) * 1975-05-15 1976-12-10 Inst Francais Du Petrole Two stroke engine lubrication - with lubricants based on trimethyol propane mixed ester compsns.
DE2551173C2 (en) * 1975-11-14 1985-09-12 Henkel KGaA, 4000 Düsseldorf Neutral complex esters
DE3924583C1 (en) * 1989-07-25 1990-11-08 Hans 7432 Bad Urach De Schur
DK0435253T3 (en) * 1989-12-28 1994-06-20 Nippon Oil Co Ltd Cooling oils for use with hydrogen-containing halogen carbon refrigerants

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EP0535990B1 (en) 1997-01-02
ATE147096T1 (en) 1997-01-15
EP0535990A1 (en) 1993-04-07
CA2079512A1 (en) 1993-04-05
JPH0598276A (en) 1993-04-20

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