JP2587296B2 - Lubricating oil composition - Google Patents

Lubricating oil composition

Info

Publication number
JP2587296B2
JP2587296B2 JP1231426A JP23142689A JP2587296B2 JP 2587296 B2 JP2587296 B2 JP 2587296B2 JP 1231426 A JP1231426 A JP 1231426A JP 23142689 A JP23142689 A JP 23142689A JP 2587296 B2 JP2587296 B2 JP 2587296B2
Authority
JP
Japan
Prior art keywords
oil
lubricating oil
present
weight
oligomer
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
JP1231426A
Other languages
Japanese (ja)
Other versions
JPH0395297A (en
Inventor
宏之 高島
▲しょう▼ 石田
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 JP1231426A priority Critical patent/JP2587296B2/en
Priority to EP90309748A priority patent/EP0416914B1/en
Priority to DE90309748T priority patent/DE69002426T2/en
Priority to KR1019900014170A priority patent/KR930011077B1/en
Publication of JPH0395297A publication Critical patent/JPH0395297A/en
Application granted granted Critical
Publication of JP2587296B2 publication Critical patent/JP2587296B2/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
    • 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
    • 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
    • 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
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
    • C—CHEMISTRY; METALLURGY
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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
    • C10M2203/022—Well-defined aliphatic compounds saturated
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/024—Well-defined aliphatic compounds unsaturated
    • C—CHEMISTRY; METALLURGY
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/04—Well-defined cycloaliphatic compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/104—Aromatic fractions
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic fractions
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    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
    • C—CHEMISTRY; METALLURGY
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    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
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    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
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    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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    • C10N2040/32—Wires, ropes or cables lubricants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/34—Lubricating-sealants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/36—Release agents or mold release agents
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/38—Conveyors or chain belts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/40—Generators or electric motors in oil or gas winning field
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/42—Flashing oils or marking oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/44—Super vacuum or supercritical use
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/50—Medical uses

Description

【発明の詳細な説明】 ［産業上の利用分野］ 本発明は潤滑油組成物に関し、詳しくは特に酸化安定
性に優れ、かつスラッジが生成しにくい潤滑油組成物に
関する。Description: TECHNICAL FIELD The present invention relates to a lubricating oil composition, and more particularly to a lubricating oil composition which is excellent in oxidative stability and hardly generates sludge.

［従来の技術および発明が解決しようとする課題］ 芳香族含有量の低い鉱油やポリα−オレフィン油等そ
の構造単位に芳香族環を含有しない合成油は、それ自身
では酸化安定性に乏しいが、酸化防止剤のレスポンスが
よく高酸化安定性の製品が得られる。しかしこのような
油は酸化防止剤に対する溶解度が低いという欠点があ
る。酸化防止剤はそれ自身が使用中に機能を果たすと変
質するものであり、この酸化による変質物がスラッジに
なると問題である。[Problems to be Solved by the Prior Art and the Invention] Synthetic oils having no aromatic ring in their structural units, such as mineral oil having low aromatic content and poly-α-olefin oil, have poor oxidation stability by themselves. In addition, a product having good antioxidant response and high oxidation stability can be obtained. However, such oils have the disadvantage of low solubility in antioxidants. The antioxidant itself is deteriorated when it performs a function during use, and there is a problem that sludge is formed by the oxidation.

長寿命潤滑油を開発する場合に重要な点は、互いに相
反するスラッジ生成の水準と酸化寿命のバランスをとる
ことにある。An important consideration in developing long-life lubricating oils is to balance the levels of conflicting sludge formation and oxidation life.

フェニル−α−ナフチルアミンは優れた酸化防止剤で
あるが、それ自身の溶解性が低く、その酸化による変質
物、およびその２量体、３量体等の多量化物はさらに溶
解度が低い欠点があるため、その優れた酸化防止性にも
かかわらず、高い酸化安定性を要求される場合でも多量
に添加して潤滑油の酸化安定性を向上させるという手段
が採れないという問題があった。Phenyl-α-naphthylamine is an excellent antioxidant, but has low solubility in itself, and has a disadvantage that its altered product due to its oxidation and its multimers such as dimers and trimers have lower solubility. Therefore, despite its excellent antioxidant properties, there has been a problem that even when high oxidation stability is required, it is not possible to take a means of adding a large amount to improve the oxidation stability of the lubricating oil.

英国特許第1,046,353号には、フェニル−α−ナフチ
ルアミンの溶解性を向上させる手段としてそのフェニル
基をさらにアルキル化する方法が開示されているが、ア
ルキル化剤としては主としてイソブチレンのオリゴマー
が用いられており、この生成物は油に対する溶解度は改
善されるものの、変質物の溶解性は依然として低いとい
う欠点があった。British Patent No. 1,046,353 discloses a method of further alkylating the phenyl group as a means of improving the solubility of phenyl-α-naphthylamine, but an oligomer of isobutylene is mainly used as an alkylating agent. Although this product has improved solubility in oil, it has the disadvantage that the solubility of the altered product is still low.

一方、ジフェニルアミンも優れた酸化防止剤の一つで
あり、ｔ−オクチル基を有するp,p′−ジ−ｔ−オクチ
ルジフェニルアミンが公知であるが、前記のフェニル−
α−ナフチルアミンと同様、多量化物の溶解度が不十分
である。On the other hand, diphenylamine is also one of the excellent antioxidants, and p, p'-di-t-octyldiphenylamine having a t-octyl group is known.
Like α-naphthylamine, the solubility of the multimer is insufficient.

また、特開昭59−5146号公報には、分枝鎖デドシル基
を有するアルキルジフェニルアミン、その製法、および
該アミンを含有する組成物が開示されているが、やは
り、酸化防止能力およびスラッジ抑制効果に関しては不
十分であった。JP-A-59-5146 discloses an alkyldiphenylamine having a branched-chain decyl group, a method for producing the same, and a composition containing the amine. Was insufficient.

本発明者らは、アルキルフェニル−α−ナフチルアミ
ンにおいて、特定構造のアルキル基を有するものが、ス
ラッジを抑制しながら、かつ高い酸化安定性を有するこ
とを見出し、先に特許出願している（特開昭62−181396
号公報）。The present inventors have found that an alkylphenyl-α-naphthylamine having an alkyl group having a specific structure has high oxidation stability while suppressing sludge, and has previously filed a patent application. Kaikai 62-181396
No.).

本発明は、かかる課題を解決すべくなされたもので、
酸化安定性に優れ、かつスラッジが生成しにくい潤滑油
組成物を提供することを目的とする。The present invention has been made to solve such problems.
An object of the present invention is to provide a lubricating oil composition that has excellent oxidation stability and hardly generates sludge.

本発明者らは、上記先行技術に比べてさらにスラッジ
抑制効果および酸化安定性を向上させるため研究を重ね
た結果、特定の構造を有するアルキルフェニル−α−ナ
フチルアミンおよびアルキルジフェニルアミンを特定量
添加した場合に、酸化安定性に極めて優れ、かつスラッ
ジ生成が少ない潤滑油組成物が得られることを見出し、
本発明を完成するに至った。The present inventors have conducted studies to further improve the sludge suppression effect and oxidation stability as compared with the above prior art, and as a result, when a specific amount of alkylphenyl-α-naphthylamine and alkyldiphenylamine having a specific structure is added. In addition, it has been found that a lubricating oil composition having extremely excellent oxidation stability and low sludge generation can be obtained,
The present invention has been completed.

［課題を解決するための手段］ すなわち、本発明は、 ［Ｉ］芳香族含有量30％重量以下の鉱油および／または
その構造単位に芳香族環を含有しない合成油を基油と
し、これに組成物全量に基準として、 ［II］一般式 ［式中、R1はプロピレンのオリゴマーから誘導される炭
素数12または15の分枝アルキル基を示す］ で表されるＮ−ｐ−アルキルフェニル−α−ナフチルア
ミン0.01〜5.0重量％、および ［III］一般式 ［式中、R2およびR3は同一でも異なっていてもよく、そ
れぞれプロピレンのオリゴマーから誘導される炭素数12
または15の分枝アルキル基を示す］ で表されるp,p′−ジアルキルジフェニルアミン0.01〜
5.0重量％、 を必須成分として配合してなる潤滑油組成物を提供する
ものである。[Means for Solving the Problems] That is, the present invention provides [I] a mineral oil having an aromatic content of 30% by weight or less and / or a synthetic oil containing no aromatic ring in its structural unit as a base oil, Based on the total amount of the composition, [II] general formula [Wherein R 1 represents a branched alkyl group having 12 or 15 carbon atoms derived from an oligomer of propylene] 0.01 to 5.0% by weight of Np-alkylphenyl-α-naphthylamine represented by the following formula: ] General formula [Wherein R 2 and R 3 may be the same or different and each has 12 carbon atoms derived from an oligomer of propylene.
Or 15 branched alkyl groups] p, p'-dialkyldiphenylamine 0.01 to
It is intended to provide a lubricating oil composition comprising 5.0% by weight as an essential component.

以下、本発明の内容をさらに詳細に説明する。 Hereinafter, the contents of the present invention will be described in more detail.

本発明でいう［Ｉ］基油とは、芳香族含有量30重量％
以下の鉱油および／またはその構造単位に芳香族環を含
有しない合成油である。The [I] base oil referred to in the present invention is an aromatic content of 30% by weight.
The following mineral oils and / or synthetic oils containing no aromatic ring in their structural units.

鉱油としては、40℃における動粘度が10〜10,000cS
t、好ましくは20〜1,000cStのものが一般に用いられ
る。通常、原油を蒸留して得られる潤滑油留分を任意の
精製処理、例えば溶剤精製、硫酸処理、水添精製、白土
処理等にかけて得られる鉱油を使用するのが好ましい。As a mineral oil, the kinematic viscosity at 40 ° C is 10 to 10,000 cS
t, preferably 20 to 1,000 cSt are generally used. Usually, it is preferable to use a mineral oil obtained by subjecting a lubricating oil fraction obtained by distilling crude oil to any purification treatment, for example, solvent purification, sulfuric acid treatment, hydrogenation purification, clay treatment and the like.

この鉱油としては、芳香族含有量30重量％以下、好ま
しくは20重量％以下のものが適当である。なお、ここで
いう芳香族含有量とは、ASTM Ｄ 2549−81に規定され
た方法で測定される値である。As the mineral oil, those having an aromatic content of 30% by weight or less, preferably 20% by weight or less are suitable. Here, the aromatic content is a value measured by a method specified in ASTM D 2549-81.

一方、合成油としては、その構造単位に芳香族環を含
有しないもので、40℃における動粘度10〜10,000cStの
ものが一般に用いられる。具体的には例えば、炭素数４
〜30のα−オレフィンの単独重合ないしは共重合により
得られるポリプテン、デセン−１オリゴマー等のポリ−
α−オレフィン油、ブチルステアレート、メチルラウレ
ート等に代表される脂肪族モノカルボン酸と脂肪族１価
アルコールとのモノエステル、ジ−２−エチルヘキシル
セバケート、ジオクチルアジペート、ジトリデシルグル
タレート等に代表される脂肪族２塩基酸と脂肪族１価ア
ルコールとのジエステル、トリメチロールプロパンカプ
リレート、トリメチロールプロパンペラルゴネート、ペ
ンタエリスリトール２−エチルヘキサノエート、ペンタ
エリスリトール、ペラルゴネート等に代表される脂肪族
多価アルコールの脂肪族モノカルボン酸エステル、ポリ
エチレングリコール、ポリプロピレングリコール等に代
表されるポリアルキレングリコールまたはそのモノアル
キルエーテル、ジアルキルエーテル、モノアルキルエス
テル、ジアルキルエステル、シクロドデカン、ヒドリン
ダン、ビシクロヘキシル、ターシクロヘキシル等のシク
ロパラフィン、ジシクロヘキシルブタン、ジシクロヘキ
シルプロパン等のアルキルシクロパラフィンおよびこれ
らの混合物等が挙げられる。On the other hand, synthetic oils that do not contain an aromatic ring in their structural units and have a kinematic viscosity at 40 ° C. of 10 to 10,000 cSt are generally used. Specifically, for example, carbon number 4
Polyolefins such as polybutene and decene-1 oligomer obtained by homopolymerization or copolymerization of α-olefins
α-olefin oil, butyl stearate, monoester of aliphatic monocarboxylic acid represented by aliphatic monohydric alcohol such as methyl laurate, di-2-ethylhexyl sebacate, dioctyl adipate, ditridecyl glutarate, etc. Fats represented by diesters of aliphatic dibasic acids and aliphatic monohydric alcohols, trimethylolpropane caprylate, trimethylolpropaneperargonate, pentaerythritol 2-ethylhexanoate, pentaerythritol, pelargonate, etc. Polyalkylene glycols represented by aliphatic monocarboxylic acid esters of aliphatic polyhydric alcohols, polyethylene glycol, polypropylene glycol, etc. or their monoalkyl ethers, dialkyl ethers, monoalkyl esters, dialkyls Ester, cyclododecane, hydrindane, bicyclohexyl, cycloparaffins terpolymers cyclohexyl, dicyclohexyl butane, alkylcycloparaffins and mixtures thereof such as dicyclohexyl propane.

一方、本発明でいう［II］Ｎ−ｐ−アルキルフェニル
−α−ナフチルアミンとは、一般式 で表わされる化合物である。式中、R1はプロピレンのオ
リゴマー（４量体または５量体）から誘導される炭素数
12または15の分枝アルキル基を示している。On the other hand, [II] Np-alkylphenyl-α-naphthylamine referred to in the present invention is represented by the general formula: It is a compound represented by these. Wherein R 1 is the number of carbon atoms derived from a propylene oligomer (tetramer or pentamer)
Shows 12 or 15 branched alkyl groups.

また、本発明でいう［III］p,p′−ジアルキルジフェ
ニルアミンとは、一般式 で表される化合物である。式中、R2およびR3は同一でも
異なっていてもよく、それぞれプロピレンのオリゴマー
（４〜５量体）から誘導される炭素数12または15の分枝
アルキル基を示している。[III] The p, p'-dialkyldiphenylamine referred to in the present invention is represented by the general formula It is a compound represented by these. In the formula, R 2 and R 3 may be the same or different and each represents a branched alkyl group having 12 or 15 carbon atoms derived from an oligomer (4- to 5-mer) of propylene.

本発明においては、上記R1、R2およびR3がプロピレン
のオリゴマーから誘導される分枝アルキル基であること
が重要であり、同じ分枝アルキル基でもα−オレフィン
から誘導されるものでは生成物の酸化防止性能が本発明
の［II］成分および［III］成分より大きく劣り、ま
た、プロピレン以外のオレフィン、例えばイソブチレン
等のオリゴマーから誘導されるものではそれ自身が酸化
により潤滑油中にスラッジとして沈降しやすいため好ま
しくない。In the present invention, it is important that the above R 1 , R 2 and R 3 are a branched alkyl group derived from an oligomer of propylene, and even if the same branched alkyl group is derived from an α-olefin, The antioxidant performance of the product is significantly inferior to the components [II] and [III] of the present invention, and when the product is derived from an olefin other than propylene, for example, an oligomer such as isobutylene, the product itself is oxidized into the sludge in the lubricating oil. It is not preferable because it tends to settle.

また、R1、R2およびR3としてプロピレンのオリゴマー
から誘導される分枝アルキル基を用いた場合でも、その
炭素数が本発明の範囲未満の場合にはやはりそれ自身が
酸化により潤滑油中にスラッジとして沈降しやすく、ま
た炭素数が本発明の範囲を超えるものは分子中に占める
官能基の割合が小さくなり酸化防止能力が弱くなるた
め、それぞれ好ましくない。Further, even when a branched alkyl group derived from an oligomer of propylene is used as R 1 , R 2 and R 3 , if the number of carbon atoms is less than the range of the present invention, the carbon atom itself is oxidized in the lubricating oil. Those which easily settle as sludge and have a carbon number exceeding the range of the present invention are not preferred because the ratio of the functional group in the molecule becomes small and the antioxidant ability becomes weak.

本発明の［II］成分であるＮ−ｐ−アルキルフェニル
−α−ナフチルアミンおよび［III］成分であるp,p′−
ジアルキルジフェニルアミンの合成法は任意であり、公
知の方法で合成することができるが、合成の容易さの点
から、フェニル−α−ナフチルアミンまたはジフェニル
アミンとプロピレンのオリゴマーのフリーデル・クラフ
ツアルキル化反応が好ましい。この際の触媒としては、
塩化アルミニウム、塩化亜鉛、塩化鉄等の金属ハロゲン
化物や硫酸、リン酸、五酸化リン、フッ化ホウ素、酸性
白土、活性白土等の酸性触媒が用いられる。Np-alkylphenyl-α-naphthylamine as the component [II] of the present invention and p, p′- as the component [III] of the present invention.
The method of synthesizing the dialkyldiphenylamine is arbitrary, and can be synthesized by a known method.From the viewpoint of ease of synthesis, a Friedel-Crafts alkylation reaction of phenyl-α-naphthylamine or an oligomer of propylene with diphenylamine is preferable. . As a catalyst in this case,
Metal halides such as aluminum chloride, zinc chloride and iron chloride, and acidic catalysts such as sulfuric acid, phosphoric acid, phosphorus pentoxide, boron fluoride, acid clay and activated clay are used.

なお、このＮ−ｐ−アルキルフェニル−α−ナフチル
アミンの製造方法は、本出願人が先に出願した特開昭62
−181396号公報に、またp,p′−ジアルキルジフェニル
アミンの製造方法は特開昭59−5146号公報に、それぞれ
その詳細が記載されている。Incidentally, this method for producing Np-alkylphenyl-α-naphthylamine is described in Japanese Patent Application Laid-Open No.
JP-A-181396 and the method for producing p, p'-dialkyldiphenylamine are described in detail in JP-A-59-5146.

本発明における［II］成分配合量は、組成物全量を基
準として0.01〜5.0重量％、好ましくは0.1〜0.3重量％
である。また［III］成分配合量は組成物全量を基準と
して0.01〜5.0重量％、好ましくは0.1〜3.0重量％であ
る。配合量が上記範囲に満たない場合には配合効果がな
く、配合量が上記範囲を超える場合には添加量に見合う
だけの効果が得られず、経済的にも不利であるためそれ
ぞれ好ましくない。Component [II] in the present invention is used in an amount of 0.01 to 5.0% by weight, preferably 0.1 to 0.3% by weight, based on the total amount of the composition.
It is. The amount of the component (III) is 0.01 to 5.0% by weight, preferably 0.1 to 3.0% by weight, based on the total amount of the composition. When the compounding amount is less than the above range, there is no compounding effect, and when the compounding amount exceeds the above range, the effect corresponding to the added amount cannot be obtained, and it is economically disadvantageous, so it is not preferable.

また、本発明の潤滑油組成物に対して必要に応じて、
通常実用されている他の潤滑油添加剤、例えば酸化防止
剤、清浄分散剤、流動点降下剤、粘度指数向上剤、油性
剤、耐摩耗剤、極圧剤、腐食防止剤、金属不活性剤、消
泡剤、乳化剤、抗乳化剤、殺菌剤、着色剤等を添加する
こともできる。これら各種添加剤の詳細については、例
えば潤滑学会誌15巻６号あるいは桜井俊男編著「石油製
品添加剤」（幸書房）に開示されている。Also, if necessary for the lubricating oil composition of the present invention,
Other commonly used lubricating oil additives such as antioxidants, detergents and dispersants, pour point depressants, viscosity index improvers, oil agents, antiwear agents, extreme pressure agents, corrosion inhibitors, metal deactivators , An antifoaming agent, an emulsifier, a demulsifier, a bactericide, a coloring agent, and the like. The details of these various additives are disclosed in, for example, Journal of the Japan Lubrication Society, Vol. 15, No. 6, or "Petroleum Product Additives" edited by Toshio Sakurai (Koshobo).

本発明の潤滑油組成物は、酸化安定性能の要求される
潤滑油、例えば自動車エンジン油、農機用エンジン油、
ディーゼルエンジン油、船用ディーゼルエンジン油、工
業用多目的潤滑油、タービン油、油圧作動油、スピンド
ル油、油膜軸受油、冷凍機油、ギヤー油、自動変速機
油、シリンダー油、ダイナモ油、マシン油、切削油、金
属加工油等に利用できる。The lubricating oil composition of the present invention is a lubricating oil required for oxidation stability performance, for example, an automobile engine oil, an agricultural machine engine oil,
Diesel engine oil, marine diesel engine oil, industrial multi-purpose lubricating oil, turbine oil, hydraulic oil, spindle oil, oil film bearing oil, refrigeration oil, gear oil, automatic transmission oil, cylinder oil, dynamo oil, machine oil, cutting oil And metal working oil.

［実施例］ 次に実施例および比較例により本発明をさらに具体的
に説明するが、本発明はその要旨を変えない限り、これ
ら実施例に制約されるものではない。[Examples] Next, the present invention will be described more specifically with reference to examples and comparative examples. However, the present invention is not limited to these examples unless the gist is changed.

実施例１および比較例１〜４ 本発明における［II］成分であるＮ−ｐ−アルキルフ
ェニル−α−ナフチルアミンおよび［III］成分である
p,p′−ジアルキルジフェニルアミンを第１表に示す量
だけ芳香族含有量７重量％の精製鉱油（動粘度34.4cSt,
40℃）に添加し、以下に示す方法で酸化寿命およびス
ラッジの有無を調べ、その結果を第１表に示した（実施
例１）。Example 1 and Comparative Examples 1 to 4 N-p-alkylphenyl-α-naphthylamine, which is the component [II], and the component [III] in the present invention.
p, p'-Dialkyldiphenylamine was refined mineral oil having an aromatic content of 7% by weight (kinetic viscosity of 34.4 cSt,
(40 ° C.), and the oxidation life and the presence or absence of sludge were examined by the following methods. The results are shown in Table 1 (Example 1).

また比較のため、第１表に示す各種化合物を上記と同
様の精製鉱油に添加し、上記と同様に酸化寿命およびス
ラッジの有無を評価し、その結果も第１表に併記した
（比較例１〜４）。For comparison, various compounds shown in Table 1 were added to the same refined mineral oil as above, and the oxidation life and the presence or absence of sludge were evaluated in the same manner as above. The results are also shown in Table 1 (Comparative Example 1). 4).

［酸化寿命試験］ JIS K 2514 3.3に準拠し、試験温度150℃、酸素圧6.3
kg/cm2（常温）、銅線触媒という条件で回転ボンブ酸化
試験を行った。酸化寿命は酸素圧が1.75kg/cm2低下する
までの時間で評価した。[Oxidation life test] Based on JIS K 2514 3.3, test temperature 150 ° C, oxygen pressure 6.3
A rotating bomb oxidation test was performed under the conditions of kg / cm 2 (normal temperature) and a copper wire catalyst. The oxidation life was evaluated by the time until the oxygen pressure decreased by 1.75 kg / cm 2 .

［実機試験］ （寿命） 水冷クーラー付回転空気圧縮機（モーター出力5.5Kw
を用い、油温80℃、吐出圧力7.5kg f/cm2の条件で実機
寿命試験を行った。寿命は１）残存酸化試験値（JIS K
−2514 3.3による）が15min以下、２）全酸価増加（JIS
K−2501による）が急激になるインダクションポイン
ト、３）粘度増加（JIS K−2283による）が急激になる
インダクションポイントのいずれか、１つの性状変化が
起こるまでの時間を測定し、その油の寿命とした。[Actual machine test] (Life) Rotary air compressor with water-cooled cooler (motor output 5.5Kw
, A life test was conducted under the conditions of an oil temperature of 80 ° C. and a discharge pressure of 7.5 kg f / cm 2 . Life is 1) Residual oxidation test value (JIS K
-2514 3.3) is 15min or less 2) Total acid value increase (JIS
The induction point at which the viscosity increases (according to JIS K-2283), at which one of the induction points at which the viscosity increase (according to JIS K-2283) increases, is measured, and the time until one property change occurs is measured. And

（スラッジ） 実機寿命試験と同様の圧縮機を用い、同様の条件で30
00hr開放時のオイルクーラ付着の有無を目視した。(Sludge) Using the same compressor as in the actual life test, under the same conditions
The presence or absence of oil cooler adhesion at the time of opening for 00 hours was visually observed.

第１表に示す結果から明らかなように、本発明に係る
実施例１の潤滑油組成物は、［II］および［III］成分
やその他の化合物をそれぞれ単独で用いた比較例１〜３
の潤滑油組成物に比べて寿命が相乗的に延び、スラッジ
の発生もなく、優れた潤滑油組成物である。また、添加
した化合物のアルキル基が本発明で規定する範囲外の比
較例４の潤滑油組成物においては、寿命は実施例１の潤
滑油組成物と同等であるが、スラッジが多量に発生し、
その性能は実施例１の潤滑油組成物に比較して大きく劣
る。 As is clear from the results shown in Table 1, the lubricating oil compositions of Example 1 according to the present invention were obtained using Comparative Examples 1 to 3 in which the components [II] and [III] and other compounds were used alone.
Is a superior lubricating oil composition having a longer life than that of the lubricating oil composition described above and no sludge generation. In the lubricating oil composition of Comparative Example 4 in which the alkyl group of the added compound was out of the range specified in the present invention, the life was the same as that of the lubricating oil composition of Example 1, but a large amount of sludge was generated. ,
Its performance is significantly inferior to the lubricating oil composition of Example 1.

［発明の効果］ 以上説明したように、特定の構造を有する［II］アル
キルフェニル−α−ナフチルアミンと［III］アルキル
ジフェニルアミンを［Ｉ］基油に一定量添加して得られ
る本発明の潤滑油組成物は、酸化安定性に極めて優れ、
かつスラッジの発生が少ない。[Effect of the Invention] As described above, the lubricating oil of the present invention obtained by adding a certain amount of [II] alkylphenyl-α-naphthylamine and [III] alkyldiphenylamine having specific structures to [I] base oil. The composition is extremely excellent in oxidative stability,
And little generation of sludge.

───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ１０Ｍ 105:32） Ｃ１０Ｎ 30:10 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 6 Identification code Agency reference number FI Technical display location C10M 105: 32) C10N 30:10

Claims (1)

(57)【特許請求の範囲】(57) [Claims] 【請求項１】［Ｉ］芳香族含有量30重量％以下の鉱油お
よび／またはその構造単位に芳香族環を含有しない合成
油を基油として、これに組成物全量を基準として、 ［II］一般式 ［式中、R1はプロピレンのオリゴマーから誘導される炭
素数12または15の分枝アルキル基を示す］ で表されるＮ−ｐ−アルキルフェニル−α−ナフチルア
ミン0.01〜5.0重量％、および ［III］一般式 ［式中、R2およびR3は同一でも異なっていてもよく、そ
れぞれプロピレンのオリゴマーから誘導される炭素数12
または15の分枝アルキル基を示す］ で表されるp,p′−ジアルキルジフェニルアミン0.01〜
5.0重量％、 を必須成分として配合してなる潤滑油組成物。[1] A mineral oil having an aromatic content of 30% by weight or less and / or a synthetic oil containing no aromatic ring in its structural unit is used as a base oil, and based on the total amount of the composition, General formula [Wherein R 1 represents a branched alkyl group having 12 or 15 carbon atoms derived from an oligomer of propylene] 0.01 to 5.0% by weight of Np-alkylphenyl-α-naphthylamine represented by the following formula: ] General formula [Wherein R 2 and R 3 may be the same or different and each has 12 carbon atoms derived from an oligomer of propylene.
Or 15 branched alkyl groups] p, p'-dialkyldiphenylamine 0.01 to
A lubricating oil composition comprising 5.0% by weight as an essential component.
JP1231426A 1989-09-08 1989-09-08 Lubricating oil composition Expired - Lifetime JP2587296B2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP1231426A JP2587296B2 (en) 1989-09-08 1989-09-08 Lubricating oil composition
EP90309748A EP0416914B1 (en) 1989-09-08 1990-09-06 Lubricating oil compositions
DE90309748T DE69002426T2 (en) 1989-09-08 1990-09-06 Lubricating oil compositions.
KR1019900014170A KR930011077B1 (en) 1989-09-08 1990-09-07 Lubricating oil compositions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP1231426A JP2587296B2 (en) 1989-09-08 1989-09-08 Lubricating oil composition

Publications (2)

Publication Number Publication Date
JPH0395297A JPH0395297A (en) 1991-04-19
JP2587296B2 true JP2587296B2 (en) 1997-03-05

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ID=16923391

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Country Status (4)

Country Link
EP (1) EP0416914B1 (en)
JP (1) JP2587296B2 (en)
KR (1) KR930011077B1 (en)
DE (1) DE69002426T2 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995016765A2 (en) * 1993-12-15 1995-06-22 The B.F. Goodrich Company Synthetic ester lubricant stabilizer composition
JPH07188688A (en) * 1993-12-27 1995-07-25 Nippon Oil Co Ltd Lubricating oil composition for plastic working of aluminum
JP3401349B2 (en) * 1994-12-07 2003-04-28 新日本石油株式会社 Lubricating oil composition
MY145889A (en) * 2004-07-08 2012-05-15 Shell Int Research Lubricating oil composition
AU2006303337A1 (en) * 2005-10-17 2007-04-26 Shell Internationale Research Maatschappij B.V. Lubricating oil composition
JP5258162B2 (en) 2005-12-09 2013-08-07 出光興産株式会社 Lubricating oil composition
WO2008154334A1 (en) 2007-06-08 2008-12-18 Infineum International Limited Additives and lubricating oil compositions containing same
JP2011051951A (en) * 2009-09-03 2011-03-17 Jx Nippon Oil & Energy Corp Method for producing hydrindane and solvent

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4096078A (en) * 1977-06-28 1978-06-20 Texaco Inc. Synthetic aircraft turbine oil
EP0097118A3 (en) * 1982-06-10 1984-07-25 Ciba-Geigy Ag Liquid antioxidants for lubricants and elastomers
US4770802A (en) * 1986-02-04 1988-09-13 Nippon Oil Co., Ltd. Lubricating oil compositions
JP2510088B2 (en) * 1986-06-05 1996-06-26 日本石油株式会社 Lubricating oil composition

Also Published As

Publication number Publication date
DE69002426D1 (en) 1993-09-02
JPH0395297A (en) 1991-04-19
DE69002426T2 (en) 1994-03-24
EP0416914B1 (en) 1993-07-28
KR910021468A (en) 1991-12-20
EP0416914A1 (en) 1991-03-13
KR930011077B1 (en) 1993-11-20

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