JPS63205394A - Lubricating oil composition - Google Patents
Lubricating oil compositionInfo
- Publication number
- JPS63205394A JPS63205394A JP3851587A JP3851587A JPS63205394A JP S63205394 A JPS63205394 A JP S63205394A JP 3851587 A JP3851587 A JP 3851587A JP 3851587 A JP3851587 A JP 3851587A JP S63205394 A JPS63205394 A JP S63205394A
- Authority
- JP
- Japan
- Prior art keywords
- lubricating oil
- temp
- compd
- ester
- formula
- 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.)
- Pending
Links
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 13
- 239000000203 mixture Substances 0.000 title claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 9
- 125000002723 alicyclic group Chemical group 0.000 abstract description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 abstract description 3
- 230000001050 lubricating effect Effects 0.000 abstract description 3
- 239000010689 synthetic lubricating oil Substances 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- -1 ester compound Chemical class 0.000 description 14
- 239000003921 oil Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000005461 lubrication Methods 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000002199 base oil Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- PMUPSYZVABJEKC-UHFFFAOYSA-N 1-methylcyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)CCCCC1C(O)=O PMUPSYZVABJEKC-UHFFFAOYSA-N 0.000 description 1
- ODGCZQFTJDEYNI-UHFFFAOYSA-N 2-methylcyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)C=CCCC1C(O)=O ODGCZQFTJDEYNI-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- DFHRKKNQGGEVPA-YPKPFQOOSA-N [(z)-octadec-9-enyl] octanoate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC DFHRKKNQGGEVPA-YPKPFQOOSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 230000002475 laxative effect Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Lubricants (AREA)
Abstract
Description
【発明の詳細な説明】 ［産業上の利用分野］ 本発明は、潤滑油組成物に関する。[Detailed description of the invention] [Industrial application field] TECHNICAL FIELD This invention relates to lubricating oil compositions.
［従来の技術及び発明が解決しようとする問題点］一般
にエステル系の合成潤滑油は、鉱油系の潤滑油に比べて
熱安定性、酸化安定性、低温流動性に優れ、温度による
粘度変化が小ざく、又、他の合成潤滑油（ポリオレフィ
ン、ポリエーテル等）と比べてもバランスのよい性状を
有することにより、近年エンジン油、計器油、ポンプ油
等の各種分野において広く利用されている。[Prior art and problems to be solved by the invention] In general, ester-based synthetic lubricating oils have superior thermal stability, oxidation stability, and low-temperature fluidity compared to mineral oil-based lubricating oils, and their viscosity changes with temperature. Due to its well-balanced properties compared to other synthetic lubricating oils (polyolefin, polyether, etc.), it has recently been widely used in various fields such as engine oil, instrument oil, and pump oil.
しかし、最近潤滑油を使用する機器の発達が著しく、潤
滑油にもこれまで以上に苛酷な条件下でも使用し得るよ
うな性能が要求されている。However, recently, equipment that uses lubricating oil has made remarkable progress, and lubricating oil is required to have performance that allows it to be used even under harsher conditions than ever before.
［発明が解決しようとする問題点］
そこで、本発明者らは、新規なエステル系合成潤滑油を
開発すべく鋭意検討の結果、特定の構造を有するエステ
ルが優れた潤滑性を示し、かつバランス良く物理的、化
学的性状を示すことを見い出し、この知見に基づいて本
発明を完成するに至った。[Problems to be Solved by the Invention] Therefore, as a result of intensive studies to develop a new ester-based synthetic lubricant, the present inventors found that an ester having a specific structure exhibits excellent lubricity and has a balanced It was discovered that it exhibits good physical and chemical properties, and based on this knowledge, the present invention was completed.
即ち、本発明は特定の構造を有するエステルを必須成分
として含有する新規な潤滑油組成物を提供することを目
的とする。That is, an object of the present invention is to provide a novel lubricating oil composition containing an ester having a specific structure as an essential component.
［問題点を解決するための手段］
本発明に係る潤滑油組成物は、下記の一般式（Ｉ）で示
されるごとき、アルコール残基中に不飽和結合を含むエ
ステル化合物を含有することを 。[Means for Solving the Problems] The lubricating oil composition according to the present invention contains an ester compound containing an unsaturated bond in the alcohol residue, as represented by the following general formula (I).
特徴とする。Features.
Ｘ→Ｃ００Ｒ）。 （Ｉ＞
（式中、Ｘは置換基を有していてもよい炭素数２〜２２
の脂肪族、脂環式若しくは芳香族の、モノ若しくは多価
カルホン酸残基を、Ｒは同一又は異なっていてもよい炭
素数１２〜２２のアルケニル基を表わす。ｎは１〜５の
整数である。〉上記化合物は、下記の一般式（ＩＩ＞で
表わされるアルコールと脂肪族、脂環式若しくは芳香族
の、モノ若しくは多価カルボン酸とを原料にして、一般
的なエステル製造法により容易に得ることができる。X→C00R). (I> (wherein, X has 2 to 22 carbon atoms, which may have a substituent)
R represents an alkenyl group having 12 to 22 carbon atoms which may be the same or different. n is an integer from 1 to 5. 〉The above compound can be easily obtained by a general ester production method using an alcohol represented by the following general formula (II>) and an aliphatic, alicyclic or aromatic mono- or polyhydric carboxylic acid as raw materials. be able to.
Ｒ−ＯＨ（ＩＩ）
（式中、Ｒは炭素数１２〜２２のアルケニル基を表わす
。）
アルコール成分として、具体的には、ドデセニルアルコ
ール、テトラデセニルアルコール、ヘキサデセニルアル
コール、オクタデセニルアルコール、エイコセニルアル
コール、トコセニルアルコール、オクタデカジェニルア
ルコール
力トリエニルアルコール等か例示される。R-OH(II) (In the formula, R represents an alkenyl group having 12 to 22 carbon atoms.) As the alcohol component, specifically, dodecenyl alcohol, tetradecenyl alcohol, hexadecenyl alcohol , octadecenyl alcohol, eicocenyl alcohol, tococenyl alcohol, octadecagenyl alcohol, trienyl alcohol, and the like.
アルコールの炭素数が上記で特定した範囲から外れると
所定の効果が得られにくい。When the number of carbon atoms in the alcohol is outside the range specified above, it is difficult to obtain the desired effect.
酸成分としては、醋酸、カプリン酸、カプロン酸、クエ
ン酸、セバシン酸、シトラコン酸、アジピン酸、ブタン
テトラカルホン酸（ ｍｅｓｏ体、１体）等の脂肪族カ
ルボン酸、安息香酸、フタル酸、テレフタル酸、トリメ
リット酸、ピロメリツｌ−酸等の芳香族カルボン酸、テ
トラヒドロフタル酸、メチルテトラヒドロフタル酸、ヘ
キサヒドロフタル酸、メチルへキサヒドロフタル酸等の
脂環式カルボン酸並びにこれらのカルボン酸の無水物等
が例示される。As acid components, aliphatic carboxylic acids such as acetic acid, capric acid, caproic acid, citric acid, sebacic acid, citraconic acid, adipic acid, butanetetracarphonic acid (meso form, 1 form), benzoic acid, phthalic acid, Aromatic carboxylic acids such as terephthalic acid, trimellitic acid, pyromellitic l-acid, alicyclic carboxylic acids such as tetrahydrophthalic acid, methyltetrahydrophthalic acid, hexahydrophthalic acid, methylhexahydrophthalic acid, and these carboxylic acids Examples include anhydrides and the like.
これらのアルコール成分及び酸成分は単独で用いてもよ
いし、２種以上の混合物として用いてもよい。These alcohol components and acid components may be used alone or as a mixture of two or more.
本発明に係る潤滑油組成物にあっては、一般式（Ｉ＞で
表わされるエステルを単独で潤滑油の基油としてもよい
が、汎用の鉱油や他の合成油を併用してもよい。In the lubricating oil composition according to the present invention, the ester represented by the general formula (I>) may be used alone as the base oil of the lubricating oil, but a general-purpose mineral oil or other synthetic oil may be used in combination.
ここで鉱油とは、ナフテン系、パラフィン系等、一般に
潤滑油基油して知られているものをいう。Here, the mineral oil refers to what is generally known as a lubricating oil base oil, such as a naphthenic oil or a paraffin oil.
又、合成油としては、ポリオレフィン、各種ジエチル、
ヒンダードエステル、ポリフェニルエーテル、ポリアル
キレングリコール、リン酸エステル、ケイ酸エステル、
シリコーン油、フロロエステル等が例示される。In addition, as synthetic oils, polyolefins, various diethyl,
Hindered ester, polyphenyl ether, polyalkylene glycol, phosphate ester, silicate ester,
Examples include silicone oil and fluoroester.
本発明に係る潤滑油組成物には、必要に応じて酸化防止
剤、清浄剤、極圧剤、油性剤、防錆剤、粘度指数面下剤
、流動点降下剤、耐摩耗剤、腐蝕防止剤、金属不活性化
剤、消泡剤、乳化剤等の各種添加剤を適宜配合すること
ができる。The lubricating oil composition according to the present invention may optionally contain an antioxidant, a detergent, an extreme pressure agent, an oily agent, a rust preventive agent, a viscosity index laxative, a pour point depressant, an anti-wear agent, and a corrosion inhibitor. , metal deactivators, antifoaming agents, emulsifiers, and other various additives may be appropriately blended.
本発明に係るエステルは、一般的な作動油、金属加工油
等の成分として幅広く使用することができる。The ester according to the present invention can be widely used as a component of general hydraulic fluids, metal working fluids, and the like.
［実 施 例コ 次に実施例をもって本発明の詳細な説明する。[Implementation example] Next, the present invention will be explained in detail with reference to Examples.
実施例１
フタル酸ジオレイル（以下、「エステルＡ」又は第１表
中「Ａ」と略称する。）について動粘度、粘度指数、動
摩擦係数、流動点並びに潤滑性能を測定した。得られた
結果を第１表に一覧する。Example 1 The kinematic viscosity, viscosity index, dynamic friction coefficient, pour point, and lubrication performance of dioleyl phthalate (hereinafter abbreviated as "ester A" or "A" in Table 1) were measured. The results obtained are listed in Table 1.
尚、各物性値は、以下の方法により測定した。In addition, each physical property value was measured by the following method.
（動粘度）
ウベローデ粘度計を用いてＪ Ｉｓ−に−２２８３に準
拠して測定した。(Kinematic viscosity) Measured using an Ubbelohde viscometer in accordance with JIS-2283.
（粘度指数）
４０’Ｃ及び１００’Ｃにおける動粘度よりＪＩＳ−に
−２２８４に準拠して算出した。(Viscosity index) Calculated from kinematic viscosity at 40'C and 100'C in accordance with JIS-2284.
（動摩擦係数〉 振子型油性摩擦試験機を用いて２５°Ｃにて測定した。(Dynamic friction coefficient) Measurement was performed at 25°C using a pendulum type oil-based friction tester.
（流動点） Ｊ Ｉｓ−に−２２６９に準拠して測定した。(Pour point) Measured according to JIS-2269.
（潤滑性能）
総合的に判断して、優れている順に◎、○、△、×の４
段階に評価した。(Lubrication performance) Based on the overall judgment, ◎, ○, △, × in order of superiority
Rated in stages.
実施例２〜６
実施例１と同様にして、下記の各種エステルの物性を測
定した。Examples 2 to 6 In the same manner as in Example 1, the physical properties of the following various esters were measured.
１．２，３．４−テトラカルボン酸テトラ（ヘキサデセ
ニル）・・・第１表中ｒＢＪ又は第２表中１エステルＢ
」と略称する。1.2,3.4-tetracarboxylic acid tetra(hexadecenyl)... rBJ in Table 1 or 1 ester B in Table 2
” is abbreviated as “.
１．２，３．４−テトラカルリボン酸テｌ〜ラオレイル
・・・第１表中「Ｃ」と略称する。1.2,3.4-tetracarribonic acid tel-laoleyl...abbreviated as "C" in Table 1.
アジピン酸オレイル・・・第１表中ｒＤＪと略称する。Oleyl adipate: Abbreviated as rDJ in Table 1.
カプリル酸オレイル・・・第１表中ｒＥＪと略称する。Oleyl caprylate: Abbreviated as rEJ in Table 1.
ヘキサヒドロフタル酸ジ（ヘキサデセニル）・・・第１
表中ｒＦＪと略称する。Di(hexadecenyl) hexahydrophthalate...1st
It is abbreviated as rFJ in the table.
得られた結果を第１表に示した。The results obtained are shown in Table 1.
実施例７〜１０
第２表に示す組成に従って調製した組成物について実施
例１と同様に各物性並びに潤滑性能を測定した。得られ
た結果を第２表に一覧する。Examples 7 to 10 Physical properties and lubricating performance of compositions prepared according to the compositions shown in Table 2 were measured in the same manner as in Example 1. The results obtained are listed in Table 2.
比較例１〜２
市販の鉱油及びヒンダードエステルの１種であるペンタ
エリスリトールテトライソノナノエート（第１表中ｒＧ
Ｊと略称する。）について実施例１と同様に物性を評価
した。得られた結果を第１表に示す。Comparative Examples 1-2 Commercially available mineral oil and pentaerythritol tetrasononanoate, which is one type of hindered ester (rG in Table 1)
It is abbreviated as J. ) was evaluated for physical properties in the same manner as in Example 1. The results obtained are shown in Table 1.
比較例３
鉱油に各種添加剤を配合した組成物について実施例１と
同様に物性を評価した。得られた結果を第２表に示す。Comparative Example 3 The physical properties of a composition prepared by blending various additives with mineral oil were evaluated in the same manner as in Example 1. The results obtained are shown in Table 2.
［発明の効果］
本発明に係るエステル化合物は、単独でも充分な低温流
動性を有し、更には温度による粘度変化が小さく、非常
にバランスの良い性能を有する。[Effects of the Invention] The ester compound according to the present invention has sufficient low-temperature fluidity even when used alone, has little change in viscosity due to temperature, and has very well-balanced performance.
更に、潤滑性能についても優れている。Furthermore, it also has excellent lubrication performance.
（以下余白）(Margin below)
Claims (1)
する潤滑油組成物。 Ｘ−（ＣＯＯＲ）＿ｎ（ I ） （式中、Ｘは置換基を有していてもよい炭素数２〜２２
の脂肪族、脂環式若しくは芳香族の、モノ若しくは多価
カルボン酸残基を、Ｒは同一又は異なっていてもよい炭
素数１２〜２２のアルケニル基を表わす。ｎは１〜５の
整数である。）[Scope of Claims] A lubricating oil composition characterized by containing a compound represented by general formula (I). X-(COOR)_n(I) (wherein, X has 2 to 22 carbon atoms, which may have a substituent)
R represents an alkenyl group having 12 to 22 carbon atoms which may be the same or different. n is an integer from 1 to 5. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3851587A JPS63205394A (en) | 1987-02-21 | 1987-02-21 | Lubricating oil composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3851587A JPS63205394A (en) | 1987-02-21 | 1987-02-21 | Lubricating oil composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63205394A true JPS63205394A (en) | 1988-08-24 |
Family
ID=12527408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3851587A Pending JPS63205394A (en) | 1987-02-21 | 1987-02-21 | Lubricating oil composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63205394A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997021792A1 (en) * | 1995-12-12 | 1997-06-19 | New Japan Chemical Co., Ltd. | Lubricating oil |
| JP2006249369A (en) * | 2005-03-14 | 2006-09-21 | Nippon Oil Corp | Lubricant for metal working by supplying extremely small amount of lubricant |
| CN102015980A (en) * | 2008-04-23 | 2011-04-13 | 禾大国际股份公开有限公司 | Engine lubricants |
| US8043524B2 (en) | 2006-09-15 | 2011-10-25 | Shrieve Chemical Products, Inc. | Synthetic refrigeration oil composition for HFC applications |
| JP2013117427A (en) * | 2011-12-02 | 2013-06-13 | Mitsubishi Heavy Ind Ltd | Deterioration evaluation device for lubricating oil and deterioration evaluation system for lubricating oil |
-
1987
- 1987-02-21 JP JP3851587A patent/JPS63205394A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997021792A1 (en) * | 1995-12-12 | 1997-06-19 | New Japan Chemical Co., Ltd. | Lubricating oil |
| JP2006249369A (en) * | 2005-03-14 | 2006-09-21 | Nippon Oil Corp | Lubricant for metal working by supplying extremely small amount of lubricant |
| US8043524B2 (en) | 2006-09-15 | 2011-10-25 | Shrieve Chemical Products, Inc. | Synthetic refrigeration oil composition for HFC applications |
| US8123974B2 (en) | 2006-09-15 | 2012-02-28 | Shrieve Chemical Products, Inc. | Synthetic refrigeration oil composition for HFC applications |
| US20120161065A1 (en) * | 2006-09-15 | 2012-06-28 | Shrieve Chemical Products, Inc. | Synthetic refrigeration oil composition for hfc applications |
| US8268188B2 (en) | 2006-09-15 | 2012-09-18 | Shrieve Chemical Products, Inc. | Synthetic refrigeration oil composition for HFC applications |
| US8709276B2 (en) * | 2006-09-15 | 2014-04-29 | Shrieve Chemical Products, Inc. | Synthetic refrigeration oil composition for HFC applications |
| CN102015980A (en) * | 2008-04-23 | 2011-04-13 | 禾大国际股份公开有限公司 | Engine lubricants |
| US8673831B2 (en) | 2008-04-23 | 2014-03-18 | Croda International Plc | Engine lubricants |
| JP2013117427A (en) * | 2011-12-02 | 2013-06-13 | Mitsubishi Heavy Ind Ltd | Deterioration evaluation device for lubricating oil and deterioration evaluation system for lubricating oil |
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