JP7476534B2 - Lubricating oil composition and mechanical device - Google Patents
Lubricating oil composition and mechanical device Download PDFInfo
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- JP7476534B2 JP7476534B2 JP2019234469A JP2019234469A JP7476534B2 JP 7476534 B2 JP7476534 B2 JP 7476534B2 JP 2019234469 A JP2019234469 A JP 2019234469A JP 2019234469 A JP2019234469 A JP 2019234469A JP 7476534 B2 JP7476534 B2 JP 7476534B2
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- 239000000203 mixture Substances 0.000 title claims description 44
- 239000010687 lubricating oil Substances 0.000 title claims description 39
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims description 59
- 229910003472 fullerene Inorganic materials 0.000 claims description 23
- 239000003921 oil Substances 0.000 claims description 17
- 239000002199 base oil Substances 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 13
- 239000003507 refrigerant Substances 0.000 claims description 10
- 239000002480 mineral oil Substances 0.000 claims description 9
- 238000005057 refrigeration Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 235000010446 mineral oil Nutrition 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- -1 dodecyloxy, hexadecyloxy Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004001 thioalkyl group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000000758 substrate Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000010721 machine oil Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000005498 polishing Methods 0.000 description 3
- 229920013639 polyalphaolefin Polymers 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- LLEFDCACDRGBKD-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;nonanoic acid Chemical compound CCC(CO)(CO)CO.CCCCCCCCC(O)=O LLEFDCACDRGBKD-UHFFFAOYSA-N 0.000 description 1
- CWTQBXKJKDAOSQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;octanoic acid Chemical compound CCC(CO)(CO)CO.CCCCCCCC(O)=O CWTQBXKJKDAOSQ-UHFFFAOYSA-N 0.000 description 1
- 239000004135 Bone phosphate Substances 0.000 description 1
- DJBVDAUKGXUPLO-QEMDMZNVSA-N C(C)C(C(=O)O)CCCC.C([C@H](O)[C@H](O)CO)O.C([C@H](O)[C@H](O)CO)O.C([C@H](O)[C@H](O)CO)O.C([C@H](O)[C@H](O)CO)O.C([C@H](O)[C@H](O)CO)O Chemical compound C(C)C(C(=O)O)CCCC.C([C@H](O)[C@H](O)CO)O.C([C@H](O)[C@H](O)CO)O.C([C@H](O)[C@H](O)CO)O.C([C@H](O)[C@H](O)CO)O.C([C@H](O)[C@H](O)CO)O DJBVDAUKGXUPLO-QEMDMZNVSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- URGQBRTWLCYCMR-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] nonanoate Chemical compound CCCCCCCCC(=O)OCC(CO)(CO)CO URGQBRTWLCYCMR-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- FXNGWBDIVIGISM-UHFFFAOYSA-N methylidynechromium Chemical group [Cr]#[C] FXNGWBDIVIGISM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000010702 perfluoropolyether Substances 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- Lubricants (AREA)
Description
本発明は、潤滑油組成物及び機械装置に関する。 The present invention relates to a lubricating oil composition and a mechanical device.
特許文献１には、電動要素と、電動要素により駆動され、摺動部を有し、冷媒を圧縮する圧縮要素とを備えており、摺動部を潤滑させる冷凍機油に直径が１００ｐｍから１０ｎｍのフラーレンが添加されている冷媒圧縮機が開示されている。さらに、この文献には、フラーレンが潤滑油組成物（冷凍機油）に最大限溶解する割合は、０．１から０．２％であることが開示されている。 Patent Document 1 discloses a refrigerant compressor that includes an electric element and a compression element that is driven by the electric element, has a sliding part, and compresses a refrigerant, and in which fullerenes with a diameter of 100 pm to 10 nm are added to a refrigeration oil that lubricates the sliding part. Furthermore, this document discloses that the maximum solubility of fullerenes in the lubricating oil composition (refrigeration oil) is 0.1 to 0.2%.
特許文献２には、圧縮機から吐出された気相冷媒中に含まれる冷凍機油をオイルセパレータで分離し、分離された冷凍機油は油戻し配管を通じて圧縮機吸入側に戻されることが開示されている Patent document 2 discloses that the refrigeration oil contained in the gas phase refrigerant discharged from the compressor is separated by an oil separator, and the separated refrigeration oil is returned to the suction side of the compressor through an oil return pipe.
特許文献３には、フラーレンを含むことを特徴とする精密研磨剤、及び、精密研磨剤において、前記フラーレンが凝集体であることを特徴とする精密研磨剤。フラーレン凝集体を含む研磨材が開示されている。 Patent document 3 discloses a precision polishing agent that contains fullerene, and a precision polishing agent in which the fullerene is in the form of an aggregate. The precision polishing agent contains a fullerene aggregate.
特許文献４には、液状フラーレン誘導体及びその製造方法、並びに、液状フラーレン誘導体を含む導電性組成物、及び、液状フラーレン誘導体が少なくともその構成の一部とされている電気・電子素子、が開示されている。しかし、前記誘導体の潤滑油組成物への適用に関しては何も開示されていない。 Patent Document 4 discloses a liquid fullerene derivative and a method for producing the same, as well as a conductive composition containing the liquid fullerene derivative, and an electric/electronic device having a liquid fullerene derivative as at least a part of its configuration. However, there is no disclosure regarding the application of the derivative to a lubricating oil composition.
例えば特許文献１に記載のように、フラーレンは潤滑性能を向上させるための潤滑油成分として好ましく用いられているが、フラーレンの潤滑油組成物（冷凍機油）に対する溶解度は高くない。そのため、より高濃度でフラーレンを使用しようとすると、使用中の温度などの環境変化でフラーレンが析出（凝集粒子の生成）することがあった。このようになった場合、例えば、特許文献２に記載のオイルセパレータで冷凍機油成分を戻せなくなったり、油戻し配管を詰まらせたり、あるいは、フラーレンの凝集粒子は特許文献３に記載のように研磨剤として作用し、潤滑油組成物が付加されている摺動面を損傷させてしまったり、種々の障害が生じることがあった。 For example, as described in Patent Document 1, fullerenes are preferably used as a lubricating oil component to improve lubrication performance, but the solubility of fullerenes in lubricating oil compositions (refrigerating machine oils) is not high. Therefore, when attempting to use fullerenes at higher concentrations, fullerenes may precipitate (generate aggregated particles) due to environmental changes such as temperature during use. When this occurs, various problems may occur, such as the oil separator described in Patent Document 2 being unable to return refrigerating machine oil components, clogging the oil return pipe, or the aggregated particles of fullerene acting as an abrasive as described in Patent Document 3, damaging the sliding surface to which the lubricating oil composition is applied.
本発明は、以上の事情に鑑みてなされたものであり、潤滑油組成物中で前記凝集粒が生じにくい潤滑油組成物を提供することを課題としている。 The present invention was made in consideration of the above circumstances, and aims to provide a lubricating oil composition in which the above-mentioned aggregate particles are less likely to occur.
本発明は、上記課題を解決するため、以下の手段を提供する。 To solve the above problems, the present invention provides the following means.
［１］ 基油と液状のフラーレン誘導体とを含む潤滑油組成物。
［２］ 前記基油が、鉱物油または合成油である前項［１］に記載の潤滑油組成物。
［３］ 前記フラーレン誘導体は、式（１）；
で表わされ、前記第１～第３のアルキル系置換基Ｒ１、Ｒ２およびＲ３は、それぞれ、アルキル（ＣｎＨ２ｎ＋１）、アルコキシル（ＯＣｎＨ２ｎ＋１）、および、チオアルキル（ＳＣｎＨ２ｎ＋１）からなる群から選択される（ここでｎは、１２以上の整数である）、
前項［１］または［２］に記載の潤滑油組成物。
［４］ 前記フラーレン誘導体は、その構造中のフラーレンがＣ６０またはＣ７０である誘導体、あるいはそれら誘導体の混合物である前項［１］または［２］に記載の潤滑油組成物。
［５］ 摺動部を有し、前記摺動部に前項［１］～［４］のいずれかに記載の潤滑油組成物が付加されている機械装置。
［６］ 前記機械装置が、冷媒を圧縮する冷媒圧縮機である前項［５］に記載の機械装置。
［７］ 前記機械装置が、冷凍装置である前項［５］に記載の機械装置。
[1] A lubricating oil composition comprising a base oil and a liquid fullerene derivative.
[2] The lubricating oil composition according to the above item [1], wherein the base oil is a mineral oil or a synthetic oil.
[3] The fullerene derivative is represented by formula (1);
wherein the first to third alkyl substituents R 1 , R 2 and R 3 are each selected from the group consisting of alkyl (C n H 2n+1 ), alkoxyl (OC n H 2n+1 ) and thioalkyl (SC n H 2n+1 ), where n is an integer of 12 or more;
The lubricating oil composition according to the above item [1] or [2].
[4] The lubricating oil composition according to the above item [1] or [2], wherein the fullerene derivative is a derivative in which the fullerene in the structure is C60 or C70 , or a mixture of such derivatives.
[5] A mechanical device having a sliding part, to which the lubricating oil composition according to any one of the above items [1] to [4] is applied.
[6] The mechanical device according to the above item [5], wherein the mechanical device is a refrigerant compressor that compresses a refrigerant.
[7] The mechanical device according to the above item [5], which is a refrigeration device.
本発明によれば、凝集粒になりにくいフラーレン誘導体を含む潤滑油組成物を提供することができる。そのため、前記凝集粒に起因する機械装置等の障害を避けることができる。 According to the present invention, it is possible to provide a lubricating oil composition containing a fullerene derivative that is less likely to form agglomerates. Therefore, it is possible to avoid damage to machinery and equipment caused by the agglomerates.
以下、本発明の一実施形態を挙げて詳細に説明する。なお、本発明はその要旨を変更しない範囲で適宜変更して実施することが可能である。 One embodiment of the present invention will be described in detail below. Note that the present invention can be modified as appropriate without departing from the spirit and scope of the invention.
本実施形態で得られる潤滑油組成物は、基油と液状のフラーレン誘導体とを含む。前記フラーレン誘導体は、液状であるため、潤滑油組成物やその溶媒などから析出しても凝集粒とはならず、前述の障害は生じない。前記溶媒としては、例えば、前記潤滑油組成物が冷凍機油であるならば冷媒が挙げられる。 The lubricating oil composition obtained in this embodiment contains a base oil and a liquid fullerene derivative. Since the fullerene derivative is liquid, it does not form aggregates even if it precipitates from the lubricating oil composition or its solvent, and the above-mentioned problems do not occur. If the lubricating oil composition is a refrigerating machine oil, for example, the solvent can be a refrigerant.
（基油）
本実施形態で使用される基油は、特に限定されるものではないが、通常、潤滑油の基油として広く使用されている鉱油及び合成油の使用が好ましい。
(Base oil)
The base oil used in this embodiment is not particularly limited, but it is preferable to use mineral oils and synthetic oils that are generally used widely as base oils for lubricating oils.
前記鉱油は、内部に含まれる二重結合を水素添加により飽和炭化水素に変換したものが一般的である。例えば、パラフィン系，ナフテン系などの基油が挙げられる。 The mineral oils are generally those in which the double bonds contained therein have been converted to saturated hydrocarbons through hydrogenation. Examples include paraffinic and naphthenic base oils.
前記合成油としては、合成炭化水素油、エーテル油、エステル油を挙げることができる。より、具体的には、ポリα－オレフィン、ジエステル、ポリアルキレングリコール、ポリアルファオレフィン、ポリアルキルビニールエーテル、ポリブテン、イソパラフィン、オレフィンコポリマー、アルキルベンゼン、アルキルナフタレン、ジイソデシルアジペート、モノエステル、二塩基酸エステル、三塩基酸エステル、ポリオールエステル（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）、ジアルキルジフェニルエーテル、アルキルジフェニルサルファイド、ポリフェニルエーテル、シリコーン潤滑油（ジメチルシリコーンなど）、パーフルオロポリエーテルなどが好適に使用できる。より好ましくは、ポリα－オレフィン、ジエステル、ポリオールエステル、ポリアルキレングリコール、ポリアルキルビニールエーテル、等を挙げることができる。 Examples of the synthetic oil include synthetic hydrocarbon oils, ether oils, and ester oils. More specifically, polyα-olefins, diesters, polyalkylene glycols, polyα-olefins, polyalkyl vinyl ethers, polybutenes, isoparaffins, olefin copolymers, alkylbenzenes, alkylnaphthalenes, diisodecyl adipates, monoesters, dibasic acid esters, tribasic acid esters, polyol esters (trimethylolpropane caprylate, trimethylolpropane pelargonate, pentaerythritol 2-ethylhexanoate, pentaerythritol pelargonate, etc.), dialkyl diphenyl ethers, alkyl diphenyl sulfides, polyphenyl ethers, silicone lubricants (dimethyl silicone, etc.), and perfluoropolyethers are preferably used. More preferably, examples of the synthetic oil include polyα-olefins, diesters, polyol esters, polyalkylene glycols, and polyalkyl vinyl ethers.
これらの鉱油や合成油は単独で使用しても良く、またこれらの中から選ばれる２種以上の基油を任意の割合で混合して使用してもよい。 These mineral oils and synthetic oils may be used alone, or two or more base oils selected from these may be mixed in any ratio.
（フラーレン誘導体）
フラーレン誘導体としては、液状のものであればよい。前記フラーレン誘導体は、通常、常温常圧（２０℃、０．１ＭＰａ）で液状であればよいが、温度や圧力など、前記潤滑油組成物の使用環境が判明している場合は、その範囲においても液状であることが好ましい。
(Fullerene derivatives)
The fullerene derivative may be any fullerene derivative that is liquid. Generally, the fullerene derivative may be liquid at room temperature and normal pressure (20° C., 0.1 MPa), but when the use environment of the lubricating oil composition, such as temperature and pressure, is known, it is preferable that the fullerene derivative is liquid within that range.
前記フラーレン誘導体の具体例としては、例えば、特許文献４に記載の液状フラーレン誘導体等が挙げられる。すなわち、下記式（１）；
で表わされ、前記第１～第３のアルキル系置換基Ｒ１、Ｒ２およびＲ３は、それぞれ、アルキル（ＣｎＨ２ｎ＋１）、アルコキシル（ＯＣｎＨ２ｎ＋１）、および、チオアルキル（ＳＣｎＨ２ｎ＋１）からなる群から選択される（ここでｎは、１２以上の整数である）、フラーレン誘導体が挙げられる。
Specific examples of the fullerene derivative include a liquid fullerene derivative described in Patent Document 4, which is represented by the following formula (1);
and the first to third alkyl substituents R 1 , R 2 and R 3 are each selected from the group consisting of alkyl (C n H 2n+1 ), alkoxyl (OC n H 2n+1 ) and thioalkyl (SC n H 2n+1 ) (wherein n is an integer of 12 or more).
前記フラーレン誘導体の構造中のフラーレンは、特に限定されず、Ｃ６０やＣ７０、さらに高次のフラーレンであってもよく、原料となるフラーレンの入手しやすさの観点から、Ｃ６０やＣ７０が好ましくは、基油への着色が少なく得られる潤滑油組成物の劣化を色で判断しやすい観点からＣ６０がより好ましい。前記フラーレン誘導体としては、これら誘導体の混合物であってもよい。この場合、Ｃ６０を有する誘導体が５０質量％以上に含まれることが好ましい。 The fullerene in the structure of the fullerene derivative is not particularly limited, and may be C60 , C70 , or higher fullerene, with C60 or C70 being preferred from the viewpoint of availability of the raw fullerene, and C60 being more preferred from the viewpoint of less coloring of the base oil and easier judgment of the deterioration of the obtained lubricating oil composition by color. The fullerene derivative may be a mixture of these derivatives. In this case, it is preferred that the derivative having C60 is contained in an amount of 50 mass% or more.
（機械装置）
本実施形態の機械装置としては、摺動部を有し、前記摺動部に前記潤滑油組成物が付加されている機械装置が挙げられる。特に、前記潤滑油組成物は、前記フラーレン誘導体による凝集粒を生じにくいので、例えば、潤滑油交換のメンテナンスを行いにくい機械装置などに好ましく適用できる。このような機械装置としてより具体的には、例えば、冷凍装置、特に、冷媒を圧縮する冷媒圧縮機が挙げられる。
(Machinery)
The mechanical device of the present embodiment may be a mechanical device having a sliding part and having the lubricating oil composition applied to the sliding part.In particular, the lubricating oil composition is less likely to generate aggregate particles due to the fullerene derivative, so it can be preferably applied to mechanical devices that are difficult to maintain by changing lubricating oil.More specifically, such mechanical devices may be refrigeration devices, particularly refrigerant compressors that compress refrigerants.
以上、本発明の好ましい実施形態について述べたが、本発明は特定の実施の形態に限定されるものではなく、特許請求の範囲内に記載された本発明の要旨の範囲内において、種々の変形・変更が可能である。 Although the preferred embodiment of the present invention has been described above, the present invention is not limited to a specific embodiment, and various modifications and variations are possible within the scope of the gist of the present invention as described in the claims.
以下、本発明の実施例について説明する。なお、本発明は以下の実施例のみに限定されるものではない。 The following describes examples of the present invention. Note that the present invention is not limited to the following examples.
（フラーレン誘導体）
以下のフラーレン誘導体Ａ，Ｂ，Ｂ２及びＣについて、特許文献４に記載の方法で分析及び合成を行った。ただし、原料のフラーレンとしてＣ６０（フロンティアカーボン（株）製、ｎａｎｏｍ（登録商標）ＳＵＨ）を用いた。また、得られた各誘導体はすべて常温常圧（２０℃、０．１ＭＰａ）で液状であった。
(Fullerene derivatives)
The following fullerene derivatives A, B, B2, and C were analyzed and synthesized by the method described in Patent Document 4. However, C 60 (nanom (registered trademark) SUH, manufactured by Frontier Carbon Co., Ltd.) was used as the raw fullerene. Furthermore, all of the obtained derivatives were liquid at room temperature and normal pressure (20° C., 0.1 MPa).
フラーレン誘導体Ａ： 前記式（１）において、Ｒ１、Ｒ２およびＲ３が－Ｏ（ＣＨ２）１１ＣＨ３であり、ｍが１であり、（Ｆｕ）がＣ６０である化合物Ｎ－メチル－２［２，４，６－トリ（ドデシルオキシ）フェニル］フレロピロリジンであり、特許文献４の実施例１の方法で得た。 Fullerene derivative A: This is the compound N-methyl-2[2,4,6-tri(dodecyloxy)phenyl]fulleropyrrolidine represented by the formula (1) in which R 1 , R 2 and R 3 are —O(CH 2 ) 11 CH 3 , m is 1 and (Fu) is C 60 , and was obtained by the method described in Example 1 of Patent Document 4.
フラーレン誘導体Ｂ： 前記式（１）において、Ｒ１、Ｒ２およびＲ３が－Ｏ（ＣＨ２）１５ＣＨ３であり、ｍが１であり、（Ｆｕ）がＣ６０である化合物Ｎ－メチル－２［２，４，６－トリ（ヘキサデシルオキシ）フェニル］フレロピロリジンであり、特許文献４の実施例２の方法で得た。 Fullerene derivative B: This is the compound N-methyl-2[2,4,6-tri(hexadecyloxy)phenyl]fulleropyrrolidine represented by the formula (1) in which R 1 , R 2 and R 3 are —O(CH 2 ) 15 CH 3 , m is 1 and (Fu) is C 60 , and was obtained by the method described in Example 2 of Patent Document 4.
フラーレン誘導体Ｂ２： 前記式（１）において、Ｒ１、Ｒ２およびＲ３が－Ｏ（ＣＨ２）１５ＣＨ３であり、ｍが２～３であり、（Ｆｕ）がＣ６０である化合物の混合物であり、特許文献４の実施例２の方法でフラーレン誘導体Ｂをカラムクロマトグラフィーで精製する際、フラーレン誘導体Ｂの不純物として分離されたものである。 Fullerene derivative B2: A mixture of compounds represented by the formula (1) in which R 1 , R 2 and R 3 are —O(CH 2 ) 15 CH 3 , m is 2 to 3, and (Fu) is C 60 , which was separated as an impurity of fullerene derivative B when fullerene derivative B was purified by column chromatography in the method of Example 2 of Patent Document 4.
フラーレン誘導体Ｃ： 前記式（１）において、Ｒ１、Ｒ２およびＲ３が－Ｏ（ＣＨ２）１９ＣＨ３であり、ｍが１であり、（Ｆｕ）がＣ６０である化合物Ｎ－メチル－２［２，４，６－トリ（エイコシルオキシ）フェニル］フレロピロリジンであり、特許文献４の実施例３の方法で得た。 Fullerene derivative C: This is N-methyl-2[ 2,4,6- tri(eicosyloxy)phenyl]fulleropyrrolidine, a compound represented by the formula (1) in which R 1 , R 2 and R 3 are —O(CH 2 ) 19 CH 3 , m is 1 and (Fu) is C 60, and was obtained by the method described in Example 3 of Patent Document 4.
（摩擦摩耗試験）
試料とする潤滑油組成物について、摩擦摩耗試験機（製品名：ボールオンディスクトライボメーター、Ａｎｔｏｎ Ｐａａｒ社製）を用いて、摩擦係数及び耐摩耗性を評価した。基板およびボールの材質を高炭素クロム軸受鋼鋼材ＳＵＪ２とした。ボールの直径を６ｍｍとした。基板の一主面に潤滑油組成物を塗布した。次に、潤滑油組成物を介して、基板の一主面上にて、ボールが同心円状の軌道を描くように、ボールを摺動させた。基板の一主面上におけるボールの速度を５０ｃｍ／秒、ボールによる基板の一主面に対する荷重を２５Ｎとした。基板の一主面上におけるボールの摺動距離が積算１０ｍの時の、平均の摩擦係数及び耐摩耗性を評価した。耐摩耗性の評価はボール面の擦り面（円形）を光学顕微鏡で観察し、擦り面の直径を測定した。
(Friction and wear test)
The friction coefficient and wear resistance of the lubricating oil composition sample were evaluated using a friction and wear tester (product name: ball-on-disk tribometer, manufactured by Anton Paar). The material of the substrate and ball was high carbon chromium bearing steel SUJ2. The diameter of the ball was 6 mm. The lubricating oil composition was applied to one main surface of the substrate. Next, the ball was slid on one main surface of the substrate through the lubricating oil composition so that the ball drew a concentric orbit. The speed of the ball on one main surface of the substrate was 50 cm/sec, and the load of the ball on one main surface of the substrate was 25 N. The average friction coefficient and wear resistance were evaluated when the sliding distance of the ball on one main surface of the substrate was an accumulated 10 m. The wear resistance was evaluated by observing the rubbing surface (circular) of the ball surface with an optical microscope and measuring the diameter of the rubbing surface.
（再溶解試験）
試料とする潤滑油組成物１０ｍｌを、２５０℃オイルバス中、ロータリーエバポレーターで留去物が観察されなくなくなるまで減圧濃縮した。得られた残留物の性状、及び、前記残留物に基油１０ｍｌを加えて攪拌したときの再溶解時の性状を、それぞれ観察した。
(Redissolution test)
10 ml of the sample lubricating oil composition was concentrated under reduced pressure in a rotary evaporator in an oil bath at 250° C. until no distillate was observed. The properties of the resulting residue and the properties of the residue when redissolved by adding 10 ml of base oil to the residue and stirring were observed.
（析出試験）
試料とする潤滑油組成物１質量部とイソブタン（代替フロンＲ６００Ａ）９質量部とを混合した。この混合物を攪拌しながら真空ポンプで減圧し、体積が１／５になるまで濃縮した。濃縮後の析出物の有無を観察した。これらの操作は、－１８℃の環境で行った。
(Precipitation test)
One part by mass of the lubricating oil composition as a sample was mixed with 9 parts by mass of isobutane (alternative to freon R600A). The mixture was stirred and reduced in pressure with a vacuum pump, and concentrated to 1/5 of its volume. The presence or absence of precipitates after concentration was observed. These operations were performed in an environment of -18°C.
（実施例１）
基油として鉱油（出光興産株式会社製、ダイアナフレシアＵ－４６）２５０ｇとフラーレン誘導体Ａ０．２５ｇとを混合し潤滑油組成物を得た。さらに、この潤滑油組成物について、摩擦摩耗試験、再溶解試験および析出試験を行った。結果を表１に示した。
Example 1
A lubricating oil composition was obtained by mixing 250 g of mineral oil (Diana Fresia U-46, manufactured by Idemitsu Kosan Co., Ltd.) as a base oil and 0.25 g of fullerene derivative A. Furthermore, this lubricating oil composition was subjected to a friction and wear test, a redissolution test, and a precipitation test. The results are shown in Table 1.
（実施例２～４）
フラーレン誘導体Ａの代わりに、フラーレン誘導体Ｂ（実施例２）、フラーレン誘導体Ｂ２（実施例３）またはフラーレン誘導体Ｃ（実施例４）を用いたことを除き、実施例１と同様に操作及び測定を行った。結果を表１に示した。
(Examples 2 to 4)
The same operations and measurements were carried out as in Example 1, except that fullerene derivative B (Example 2), fullerene derivative B2 (Example 3) or fullerene derivative C (Example 4) was used instead of fullerene derivative A. The results are shown in Table 1.
（比較例１）
基油として鉱油（出光興産株式会社製、ダイアナフレシアＵ－４６）２５０ｇと、フラーレンとしてＣ６０（フロンティアカーボン（株）製、ｎａｎｏｍ（登録商標）ＳＵＨ）０．２５ｇとを混合し、室温でマグネチックスターラーを用いて３６時間撹拌した。次に、孔径０．１μｍのメンブランフィルターで濾過し、得られた濾液を潤滑油組成物としたことを除き、実施例１と同様に操作及び測定を行った。結果を表１に示した。
(Comparative Example 1)
250 g of mineral oil (Diana Fresia U-46, manufactured by Idemitsu Kosan Co., Ltd.) as base oil and 0.25 g of C 60 (nanom (registered trademark) SUH, manufactured by Frontier Carbon Corp.) as fullerene were mixed and stirred at room temperature for 36 hours using a magnetic stirrer. Next, the mixture was filtered through a membrane filter with a pore size of 0.1 μm, and the same operations and measurements were carried out as in Example 1, except that the filtrate obtained was used as the lubricating oil composition. The results are shown in Table 1.
（比較例２）
鉱油（出光興産株式会社製、ダイアナフレシアＵ－４６）を潤滑油組成物としたこと、及び、再溶解試験を行わなかったこと、を除き実施例１と同様に操作及び測定を行った。結果を表１に示した。
(Comparative Example 2)
The same operations and measurements were carried out as in Example 1, except that mineral oil (Diana Fresia U-46, manufactured by Idemitsu Kosan Co., Ltd.) was used as the lubricating oil composition and that the redissolution test was not carried out. The results are shown in Table 1.
表１より、本実施形態の潤滑油組成物（実施例１～４）は、摩擦摩耗試験でＣ６０を用いた潤滑油組成物（比較例１）と同等の摩擦摩耗性能を有しているにもかかわらず、再溶解試験及び析出試験で析出物や固形物の残留が見られず、フラーレン化合物の凝集粒が生じにくいことが分かった。なお、比較例１の再溶解試験及び析出試験で生じた固形物は黒色でフラーレン凝集粒と考えられる。
From Table 1, it can be seen that the lubricating oil compositions of this embodiment (Examples 1 to 4) have the same friction and wear performance as the lubricating oil composition using C60 (Comparative Example 1) in the friction and wear test, but no precipitates or solid residues were observed in the redissolution test and precipitation test, and agglomerates of fullerene compounds are unlikely to form. The solids generated in the redissolution test and precipitation test of Comparative Example 1 were black and are thought to be fullerene aggregates.
Claims (7)
前記フラーレン誘導体は、式（１）；
（式中の、Ｒ １ 、Ｒ ２ およびＲ ３ は、同一または別異に、炭素原子数が少なくとも１２の第１～第３のアルキル系置換基を示し、（Ｆｕ）はフラーレンを示し、Ｘはメチル基を示し、ｍは１～３であることを示す。）
で表わされ、
前記第１～第３のアルキル系置換基Ｒ １ 、Ｒ ２ およびＲ ３ は、それぞれ、アルキル（Ｃ ｎ Ｈ ２ｎ＋１ ）、アルコキシル（ＯＣ ｎ Ｈ ２ｎ＋１ ）、および、チオアルキル（ＳＣ ｎ Ｈ ２ｎ＋１ ）からなる群から選択される（ここでｎは、１２以上の整数である）潤滑油組成物。 The liquid composition includes a base oil and a liquid fullerene derivative,
The fullerene derivative is represented by formula (1);
(In the formula, R 1 , R 2 and R 3 are the same or different and each represents a first to a third alkyl-based substituent having at least 12 carbon atoms, (Fu) represents a fullerene, X represents a methyl group, and m represents an integer of 1 to 3.)
It is expressed as
The lubricating oil composition wherein the first, second and third alkyl substituents R 1 , R 2 and R 3 are each selected from the group consisting of alkyl (C n H 2n+1 ), alkoxyl (OC n H 2n+1 ), and thioalkyl (SC n H 2n+1 ), where n is an integer equal to or greater than 12 .
前記基油が、鉱油である請求項１または２に記載の潤滑油組成物。 In the formula (1), R 1 , R 2 and R 3 each represent a linear alkylalkoxyl group having 12 to 20 carbon atoms selected from dodecyloxy, hexadecyloxy and eicosyloxy, (Fu) represents a compound having a carbon number of 60 , X represents a methyl group, m is 1, 2 or 3,
3. The lubricating oil composition according to claim 1 , wherein the base oil is a mineral oil .
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