JP2014015402A - Succinimide compound, lubricating oil additive, and lubricating oil composition - Google Patents
Succinimide compound, lubricating oil additive, and lubricating oil composition Download PDFInfo
- Publication number
- JP2014015402A JP2014015402A JP2012151824A JP2012151824A JP2014015402A JP 2014015402 A JP2014015402 A JP 2014015402A JP 2012151824 A JP2012151824 A JP 2012151824A JP 2012151824 A JP2012151824 A JP 2012151824A JP 2014015402 A JP2014015402 A JP 2014015402A
- Authority
- JP
- Japan
- Prior art keywords
- lubricating oil
- succinimide compound
- succinimide
- compound
- general 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
- 0 *C(CC(O1)=O)C1=O Chemical compound *C(CC(O1)=O)C1=O 0.000 description 1
Images
Landscapes
- Pyrrole Compounds (AREA)
- Lubricants (AREA)
Abstract
Description
本発明は、新規なコハク酸イミド化合物、並びに該化合物を含有した潤滑油添加剤及び潤滑油組成物に関する。 The present invention relates to a novel succinimide compound, and a lubricating oil additive and lubricating oil composition containing the compound.
コハク酸イミド化合物は、ガソリンエンジン油やディーゼルエンジン油などの内燃機関用潤滑油の分野において、生成する不溶解分を油中に分散させる無灰分散剤として用いられている。一方、コハク酸イミド化合物は、自動変速機などの駆動系潤滑油の分野において、摩擦力を高める摩擦調整剤として使用されている。 A succinimide compound is used as an ashless dispersant that disperses an insoluble matter to be generated in oil in the field of lubricating oil for internal combustion engines such as gasoline engine oil and diesel engine oil. On the other hand, succinimide compounds are used as friction modifiers for increasing frictional force in the field of drive system lubricants such as automatic transmissions.
従来のコハク酸イミド化合物としては、高分子量のアルケニルもしくはアルキル基で置換されたこはく酸無水物と、ポリアルキレンポリアミンとの反応により得られるコハク酸イミド化合物などが知られている（下記特許文献１〜３を参照。）また、置換コハク酸イミドの製造方法として、マレイミド化合物及びケイ素エノラートを反応させる方法が知られている（下記特許文献４を参照。）
As a conventional succinimide compound, a succinimide compound obtained by reaction of a succinic anhydride substituted with a high molecular weight alkenyl or alkyl group and a polyalkylene polyamine is known (
本発明は、内燃機関用潤滑油における無灰分散剤、駆動系潤滑油における摩擦調整剤などの用途に有用な新規なコハク酸イミド化合物、並びに該化合物を含有した潤滑油添加剤及び潤滑油組成物を提供することを目的とする。 The present invention relates to a novel succinimide compound useful for applications such as an ashless dispersant in a lubricating oil for internal combustion engines, a friction modifier in a drive system lubricating oil, and a lubricating oil additive and a lubricating oil composition containing the compound. The purpose is to provide.
上記課題を解決するために、本発明は、下記一般式（１）で表されるコハク酸イミド化合物を提供する。
［式（１）中、Ｒ１は数平均分子量５００以上５０００未満のアルキル基又は数平均分子量５００以上５０００未満のアルケニル基を示す。］
In order to solve the above problems, the present invention provides a succinimide compound represented by the following general formula (1).
[In Formula (1), R 1 represents an alkyl group having a number average molecular weight of 500 or more and less than 5000 or an alkenyl group having a number average molecular weight of 500 or more and less than 5000. ]
また、本発明は、下記一般式（２）で表される化合物と、下記式（３）で表される化合物との反応により得られるコハク酸イミド化合物を提供する。
［式（２）中、Ｒ１は数平均分子量５００以上５０００未満のアルキル基又は数平均分子量５００以上５０００未満のアルケニル基を示す。］
[In Formula (2), R 1 represents an alkyl group having a number average molecular weight of 500 or more and less than 5000 or an alkenyl group having a number average molecular weight of 500 or more and less than 5000. ]
本発明のコハク酸イミド化合物は、従来のコハク酸イミド化合物と比較して、非常に優れた特性を有するため、内燃機関用潤滑油における無灰分散剤、駆動装置用潤滑油における摩擦調整剤などの用途に有用である。 Since the succinimide compound of the present invention has very superior characteristics compared to conventional succinimide compounds, it is suitable for use in ashless dispersants in internal combustion engine lubricants, friction modifiers in drive device lubricants, etc. Useful for applications.
例えば、近時、駆動系潤滑油では、燃費効率向上の観点から自動変速機内部での摩擦力を効率よく駆動力に転換するために、従来以上の高い摩擦係数が求められている。しかし、上記の特許文献１〜３に記載されているような従来のコハク酸イミド化合物を用いた場合には、十分な摩擦特性向上効果を得ることができなかった。なお、この原因としては、従来のコハク酸イミド化合物の場合、コハク酸イミド化合物自体の摩擦特性向上効果が不十分であることに加えて、コハク酸イミドの量を増やすと金属表面への吸着性が変化してその他の添加剤のバランスを崩してしまい、結果として摩擦特性を悪化させてしまうことが考えられる。
For example, recently, drive system lubricants are required to have a higher coefficient of friction than conventional ones in order to efficiently convert the friction force inside the automatic transmission into drive force from the viewpoint of improving fuel efficiency. However, when a conventional succinimide compound as described in
それに対して、本発明のコハク酸イミド化合物は、従来のコハク酸イミド化合物と比較して、摩擦特性向上効果に優れるため、自動変速機内部での摩擦力を効率よく駆動力に転換するための高い摩擦係数を達成することができ、燃費効率を向上させることができる。 On the other hand, the succinimide compound of the present invention is superior in the effect of improving the friction characteristics as compared with the conventional succinimide compound, so that the frictional force inside the automatic transmission is efficiently converted to the driving force. A high coefficient of friction can be achieved, and fuel efficiency can be improved.
また、本発明は、上記本発明のコハク酸イミド化合物を含有する潤滑油添加剤を提供する。 The present invention also provides a lubricating oil additive containing the succinimide compound of the present invention.
また、本発明は、潤滑油基油と、上記本発明のコハク酸イミド化合物とを含有する潤滑油組成物を提供する。 The present invention also provides a lubricating oil composition comprising a lubricating base oil and the succinimide compound of the present invention.
また、本発明は、潤滑油基油と、上記本発明のコハク酸イミド化合物とを含有する無段変速機用潤滑油組成物を提供する。 Moreover, this invention provides the lubricating oil composition for continuously variable transmissions containing lubricating base oil and the said succinimide compound of this invention.
本発明の潤滑油組成物は、リン化合物をさらに含有することが好ましい。 The lubricating oil composition of the present invention preferably further contains a phosphorus compound.
本発明によれば、内燃機関用潤滑油における無灰分散剤、駆動系潤滑油における摩擦調整剤などの用途に有用な新規なコハク酸イミド化合物、並びに該化合物を含有した潤滑油添加剤及び潤滑油組成物を提供することが可能となる。 According to the present invention, a novel succinimide compound useful for applications such as an ashless dispersant in an internal combustion engine lubricating oil, a friction modifier in a drive system lubricating oil, and a lubricating oil additive and lubricating oil containing the compound It becomes possible to provide a composition.
以下、本発明の好適な実施形態について詳細に説明する。 Hereinafter, preferred embodiments of the present invention will be described in detail.
［第１実施形態；コハク酸イミド化合物］
本発明の第１実施形態に係るコハク酸イミド化合物は、下記一般式（１）で表される構造を有する。
The succinimide compound according to the first embodiment of the present invention has a structure represented by the following general formula (1).
一般式（１）中のＲ１としては、ポリブテニル基、ポリイソブテニル基が好ましい。また、数平均分子量は、５００以上５０００未満であり、好ましくは７００〜４０００、より好ましくは８００〜３５００である。 R 1 in the general formula (1) is preferably a polybutenyl group or a polyisobutenyl group. The number average molecular weight is 500 or more and less than 5000, preferably 700 to 4000, more preferably 800 to 3500.
一般式（１）で表されるコハク酸イミド化合物には、全ての光学異性体が包含される。好ましい化合物としては下記一般式（１−１）で表される化合物が挙げられる。
The succinimide compound represented by the general formula (1) includes all optical isomers. A preferable compound includes a compound represented by the following general formula (1-1).
一般式（１）で表されるコハク酸イミド化合物は、ホウ素化せずにそのまま（すなわち非ホウ素化コハク酸イミド化合物として）用いてもよく、あるいはホウ素化コハク酸イミド化合物として用いてもよい。さらに、ホウ素化コハク酸イミド化合物と非ホウ素化コハク酸イミド化合物とを組み合わせて用いてもよい。 The succinimide compound represented by the general formula (1) may be used as it is without being boronated (that is, as a non-borated succinimide compound), or may be used as a boronated succinimide compound. Further, a boronated succinimide compound and a non-borated succinimide compound may be used in combination.
ホウ素化コハク酸イミド化合物は、一般式（１）で表されるコハク酸イミド化合物に対し、ホウ素含有化合物を、通常５０〜２５０℃、好ましくは１００〜２００℃の温度で反応させることにより得ることができる。ホウ素含有化合物としては、酸化ホウ素、ハロゲン化ホウ素、ホウ酸、ホウ酸無水物及びホウ酸エステルなどが挙げられる。これらのホウ素含有化合物は、１種を単独で用いてもよく、２種以上を組み合わせて用いてもよい。 A boronated succinimide compound is obtained by reacting a boron-containing compound with a succinimide compound represented by the general formula (1) at a temperature of usually 50 to 250 ° C, preferably 100 to 200 ° C. Can do. Examples of the boron-containing compound include boron oxide, boron halide, boric acid, boric anhydride, and boric acid ester. These boron-containing compounds may be used alone or in combination of two or more.
［第２実施形態：コハク酸イミド化合物］
本発明の第２実施形態に係るコハク酸イミド化合物は、下記一般式（２）で表される化合物と、下記式（３）で表される化合物（「Ｌ−チロシンエチルエステル」とも呼ばれる。）との反応により得られるコハク酸イミド化合物である。
The succinimide compound according to the second embodiment of the present invention includes a compound represented by the following general formula (2) and a compound represented by the following formula (3) (also referred to as “L-tyrosine ethyl ester”). It is a succinimide compound obtained by reaction with.
一般式（２）中のＲ１は一般式（１）中のＲ１と同一の定義内容を示す。Ｒ１の好ましい態様も一般式（１）のＲ１の場合と同様であり、ここでは重複する説明を省略する。 R 1 in the general formula (2) represents the same definition as R 1 in general formula (1). The preferred embodiment of R 1 is also the same as in the case of R 1 in the general formula (1), and redundant explanation is omitted here.
式（３）で表される化合物には、全ての光学異性体が包含される。好ましい化合物としては、下記式（３−１）で表される化合物が挙げられる。
一般式（２）で表される化合物及び一般式（３）で表される化合物の仕込み比を適宜選定することによって、反応生成物中の一般式（１）で表されるコハク酸イミド化合物の割合を調整することが可能である。一般式（１）で表されるコハク酸イミド化合物をより確実に得ることができる点から、両者の仕込み比は、一般式（２）で表される化合物１ｍｏｌに対して、式（３）で表される化合物が、好ましくは１〜２ｍｏｌ、より好ましくは１〜１．８ｍｏｌ、さらに好ましくは１．１〜１．６ｍｏｌ、特に好ましくは１．２〜１．５ｍｏｌである。 By appropriately selecting the charge ratio of the compound represented by the general formula (2) and the compound represented by the general formula (3), the succinimide compound represented by the general formula (1) in the reaction product It is possible to adjust the ratio. From the point that the succinimide compound represented by the general formula (1) can be obtained more reliably, the charging ratio of both is represented by the formula (3) with respect to 1 mol of the compound represented by the general formula (2). The compound represented is preferably 1 to 2 mol, more preferably 1 to 1.8 mol, still more preferably 1.1 to 1.6 mol, and particularly preferably 1.2 to 1.5 mol.
一般式（２）で表される化合物と式（３）で表される化合物との反応条件は特に制限されないが、反応温度は１４５〜１８０℃、好ましくは１５５〜１７５℃であり、反応時間は１２〜３６、好ましくは１８〜２８時間である。
必要に応じて反応溶媒を用いることが出来、溶媒としては、一般式（２）で表される化合物と式（３）で表される化合物を溶解するものが好ましく、具体的には有機溶媒であり、エタノール、トルエン、キシレン類などが例示できる。
The reaction conditions of the compound represented by the general formula (2) and the compound represented by the formula (3) are not particularly limited, but the reaction temperature is 145 to 180 ° C, preferably 155 to 175 ° C, and the reaction time is 12 to 36, preferably 18 to 28 hours.
A reaction solvent can be used as necessary. As the solvent, a solvent that dissolves the compound represented by the general formula (2) and the compound represented by the formula (3) is preferable. Yes, ethanol, toluene, xylenes and the like can be exemplified.
本実施形態に係るコハク酸イミド化合物は、ホウ素化せずにそのまま（すなわち非ホウ素化コハク酸イミド化合物として）用いてもよく、あるいはホウ素化コハク酸イミド化合物として用いてもよい。さらに、ホウ素化コハク酸イミド化合物と非ホウ素化コハク酸イミド化合物とを組み合わせて用いてもよい。 The succinimide compound according to this embodiment may be used as it is without being boronated (that is, as a non-borated succinimide compound) or may be used as a boronated succinimide compound. Further, a boronated succinimide compound and a non-borated succinimide compound may be used in combination.
ホウ素化コハク酸イミド化合物は、式（１）で表されるコハク酸イミド化合物に対し、ホウ素含有化合物を、通常５０〜２５０℃、好ましくは１００〜２００℃の温度で反応させることにより得ることができる。ホウ素含有化合物としては、酸化ホウ素、ハロゲン化ホウ素、ホウ酸、ホウ酸無水物及びホウ酸エステルなどが挙げられる。これらのホウ素含有化合物は、１種を単独で用いてもよく、２種以上を組み合わせて用いてもよい。 The boronated succinimide compound can be obtained by reacting a boron-containing compound with a succinimide compound represented by the formula (1) at a temperature of usually 50 to 250 ° C, preferably 100 to 200 ° C. it can. Examples of the boron-containing compound include boron oxide, boron halide, boric acid, boric anhydride, and boric acid ester. These boron-containing compounds may be used alone or in combination of two or more.
［第３実施形態：潤滑油添加剤］
本実施形態に係る潤滑油添加剤は、上記の第１実施形態又は第２実施形態に係るコハク酸イミド化合物を含有する。当該潤滑油添加剤は、第１実施形態又は第２実施形態に係るコハク酸イミド化合物のみからなるものであってもよく、第１実施形態又は第２実施形態に係るコハク酸イミド化合物と他の添加剤との混合物であってもよい。また、当該潤滑油添加剤は、添加剤を溶解するための希釈剤をさらに含有してもよい。
[Third Embodiment: Lubricating Oil Additive]
The lubricating oil additive according to the present embodiment contains the succinimide compound according to the first embodiment or the second embodiment. The lubricating oil additive may be composed only of the succinimide compound according to the first embodiment or the second embodiment, and the succinimide compound according to the first embodiment or the second embodiment and other It may be a mixture with an additive. The lubricating oil additive may further contain a diluent for dissolving the additive.
第１実施形態及び第２実施形態に係るコハク酸イミド化合物は、潤滑油分野に用いられる各種添加剤との適合性に優れている。そのため、本実施形態に係る潤滑油添加剤が第１実施形態又は第２実施形態に係るコハク酸イミド化合物と他の添加剤との混合物である場合、併用される他の添加剤の種類は特に制限されず、第１実施形態又は第２実施形態に係るコハク酸イミド化合物と併用される他の添加剤の種類並びに両者の配合量は、潤滑油添加剤の用途・目的に応じて適宜選定することができる。併用される他の添加剤の具体例は後述する。 The succinimide compounds according to the first embodiment and the second embodiment are excellent in compatibility with various additives used in the lubricating oil field. Therefore, when the lubricating oil additive according to the present embodiment is a mixture of the succinimide compound according to the first embodiment or the second embodiment and other additives, the types of other additives used in combination are particularly The type of the other additive used in combination with the succinimide compound according to the first embodiment or the second embodiment and the blending amount of both are appropriately selected according to the use and purpose of the lubricant additive. be able to. Specific examples of other additives used in combination will be described later.
［第４実施形態：潤滑油組成物］
本発明の第４実施形態に係る潤滑油組成物は、潤滑油基油と、上記第１実施形態又は第２実施形態に係るコハク酸イミド化合物とを含有する。なお、当該潤滑油組成物には、潤滑油基油と、上記第３実施形態に係る潤滑油添加剤とを含有する態様が包含される。
[Fourth Embodiment: Lubricating Oil Composition]
The lubricating oil composition according to the fourth embodiment of the present invention contains a lubricating base oil and the succinimide compound according to the first embodiment or the second embodiment. In addition, the aspect containing the lubricating oil base oil and the lubricating oil additive which concerns on the said 3rd Embodiment is included by the said lubricating oil composition.
潤滑油基油としては特に制限されず、鉱油及び合成油のいずれも使用することができる。鉱油としては、従来公知の種々のものが使用可能であり、例えば、パラフィン基系鉱油、中間基系鉱油、ナフテン基系鉱油などが挙げられる。具体的には、溶剤精製又は水素精製による軽質ニュートラル油、中間ニュートラル油、重質ニュートラル油又はブライトストックなどを挙げることができる。また、ワックスを異性化したＧＴＬ基油などを用いてもよく、精製度が上がるほどその効果は高くなる。 The lubricant base oil is not particularly limited, and any of mineral oil and synthetic oil can be used. Various conventionally known oils can be used as the mineral oil, and examples thereof include paraffin-based mineral oil, intermediate-based mineral oil, and naphthene-based mineral oil. Specifically, light neutral oil, intermediate neutral oil, heavy neutral oil, bright stock, etc. by solvent refining or hydrogen refining can be mentioned. Alternatively, GTL base oil obtained by isomerizing wax may be used, and the effect increases as the degree of purification increases.
また、合成油としては、同様に従来公知の種々のものが使用可能である。例えば、ポリα―オレフィン（α―オレフィン共重合体を含む）、ポリブテン、ポリオールエステル、二塩基酸エステル、リン酸エステル、ポリフェニルエーテル、アルキルベンゼン、アルキルナフタレン、ポリオキシアルキレングリコール、ネオペンチルグリコール、シリコーンオイル、トリメチロールプロパン、ペンタエリスリトール、さらにはヒンダードエステルなどを用いることができる。 As the synthetic oil, various conventionally known oils can be used. For example, poly α-olefin (including α-olefin copolymer), polybutene, polyol ester, dibasic acid ester, phosphate ester, polyphenyl ether, alkylbenzene, alkylnaphthalene, polyoxyalkylene glycol, neopentyl glycol, silicone Oil, trimethylolpropane, pentaerythritol, hindered ester and the like can be used.
これらの潤滑油基油は、１種を単独で、あるいは２種以上を組み合わせて使用することができ、鉱油と合成油とを組み合わせて使用してもよい。 These lubricating base oils can be used alone or in combination of two or more, and may be used in combination of mineral oil and synthetic oil.
潤滑油基油の動粘度は、潤滑油組成物の用途・目的に応じて適宜選定することができる。例えば、本実施形態に係る潤滑油組成物を駆動系潤滑油として用いる場合、潤滑油基油の１００℃における動粘度は、好ましくは１〜３０ｍｍ２／ｓ、より好ましくは２〜２０ｍｍ２／ｓ、さらに好ましくは３〜１０ｍｍ２／ｓである。１００℃における動粘度が上記範囲にあると、自動変速機のギア軸受けやクラッチなどの摺動部における摩擦を十分に低減し得ると共に低温特性も良好となる。一方、１００℃における動粘度が３０ｍｍ２／ｓを超えると、燃費が悪化し、また低温粘度が高くなりすぎる傾向にある。また、１００℃における動粘度が１ｍｍ２／ｓ未満であると、自動変速機のギア軸受けやクラッチ等の摺動部において摩耗量が増加するなど潤滑性能が低下したり、蒸発性が高くなり潤滑油消費量が多くなるおそれがある。 The kinematic viscosity of the lubricating base oil can be appropriately selected according to the use and purpose of the lubricating oil composition. For example, when using a lubricating oil composition according to the present embodiment as the drive system a lubricating oil, a kinematic viscosity at 100 ° C. of the lubricating base oil is preferably 1 to 30 mm 2 / s, more preferably 2 to 20 mm 2 / s More preferably, it is 3-10 mm < 2 > / s. When the kinematic viscosity at 100 ° C. is in the above range, friction at sliding parts such as gear bearings and clutches of the automatic transmission can be sufficiently reduced and the low temperature characteristics are also good. On the other hand, if the kinematic viscosity at 100 ° C. exceeds 30 mm 2 / s, the fuel efficiency deteriorates and the low-temperature viscosity tends to be too high. Further, if the kinematic viscosity at 100 ° C. is less than 1 mm 2 / s, the lubrication performance is lowered such as an increase in wear amount in sliding parts such as gear bearings and clutches of the automatic transmission, and the evaporating property is increased, resulting in lubrication. Oil consumption may increase.
また、潤滑油基油の％ＣＡは、低温特性の点から、２０以下であるものが好ましく、特に１０以下であることがより好ましい。 Further,% CA of the lubricating base oil is preferably 20 or less, more preferably 10 or less, from the viewpoint of low temperature characteristics.
本実施形態に係る潤滑油組成物において、式（１）で表されるコハク酸イミド化合物の含有量は、その添加効果を有効に発揮し得る点から、好ましくは０．０１〜３０質量％、より好ましくは０．０５〜２０質量％、さらに好ましくは０．１〜１０質量％である。 In the lubricating oil composition according to the present embodiment, the content of the succinimide compound represented by the formula (1) is preferably 0.01 to 30% by mass from the viewpoint that the additive effect can be effectively exhibited. More preferably, it is 0.05-20 mass%, More preferably, it is 0.1-10 mass%.
本実施形態に係る潤滑油組成物は、その性能をさらに向上させる目的で、必要に応じて、第１実施形態又は第２実施形態に係るコハク酸イミド化合物以外の添加剤をさらに含有することができる。当該添加剤としては、式（１）で表されるコハク酸イミド化合物以外の無灰分散剤及び／又は摩擦調整剤、金属系清浄剤、粘度指数向上剤、極圧添加剤、酸化防止剤、腐食防止剤、消泡剤、着色剤等が挙げられる。これらの添加剤は、１種を単独で、又は２種以上を組み合わせて用いることができる。 The lubricating oil composition according to the present embodiment may further contain additives other than the succinimide compound according to the first embodiment or the second embodiment, as necessary, for the purpose of further improving the performance. it can. Such additives include ashless dispersants and / or friction modifiers other than the succinimide compounds represented by formula (1), metal detergents, viscosity index improvers, extreme pressure additives, antioxidants, corrosion An inhibitor, an antifoamer, a coloring agent, etc. are mentioned. These additives can be used individually by 1 type or in combination of 2 or more types.
第１実施形態又は第２実施形態に係るコハク酸イミド化合物以外の無灰分散剤及び／摩擦調整剤としては、脂肪酸エステル、脂肪酸アミド、又は、リン酸エステル、亜リン酸エステル、チオリン酸エステルなどのリン化合物、ＭｏＤＴＰ、ＭｏＤＴＣなどの有機モリブデン化合物、ＺｎＤＴＰなどの有機亜鉛化合物、アルキルメルカプチルボレートなどの有機ホウ素化合物、グラファイト、二硫化モリブデン、硫化アンチモン、ホウ素化合物、ポリテトラフルオロエチレンなどの固体潤滑剤系摩擦調整剤などが挙げられ、これら中でも、リン化合物が好ましい。無灰分散剤及び／又は摩擦調整剤の含有量は、潤滑油組成物全量を基準として、通常０．１〜１０質量％である。 Ashless dispersants and / or friction modifiers other than succinimide compounds according to the first embodiment or the second embodiment include fatty acid esters, fatty acid amides, phosphate esters, phosphite esters, thiophosphate esters, and the like. Solid lubricants such as phosphorus compounds, organomolybdenum compounds such as MoDTP, MoDTC, organozinc compounds such as ZnDTP, organoboron compounds such as alkyl mercaptoylborate, graphite, molybdenum disulfide, antimony sulfide, boron compounds, polytetrafluoroethylene, etc. System friction modifiers and the like. Among these, phosphorus compounds are preferable. The content of the ashless dispersant and / or the friction modifier is usually 0.1 to 10% by mass based on the total amount of the lubricating oil composition.
酸化防止剤としては、例えばアルキル化ジフェニルアミン、フェニル−α−ナフチルアミン、アルキル化−α−ナフチルアミンなどのアミン系酸化防止剤、２，６−ジ−ｔ−ブチル−４−メチルフェノール、４，４’−メチレンビス（２，６−ジ−ｔ−ブチルフェノール）などのフェノール系酸化防止剤などが挙げられる。酸化防止剤の含有量は、潤滑油組成物全量を基準として、通常０．０５〜５質量％である。 Examples of the antioxidant include amine-based antioxidants such as alkylated diphenylamine, phenyl-α-naphthylamine, alkylated-α-naphthylamine, 2,6-di-t-butyl-4-methylphenol, 4,4 ′. -Phenolic antioxidants such as -methylenebis (2,6-di-t-butylphenol). The content of the antioxidant is usually 0.05 to 5% by mass based on the total amount of the lubricating oil composition.
金属系清浄剤としては、例えば、カルシウムスルホネート、マグネシウムスルホネート、バリウムスルホネート、カルシウムサリチレート、マグネシウムサリチレート、カルシウムフェネート、バリウムフェネートなどが挙げられ、金属系清浄剤の含有量は、潤滑油組成物全量を基準として、通常０．１〜１０質量％である。 Examples of metallic detergents include calcium sulfonate, magnesium sulfonate, barium sulfonate, calcium salicylate, magnesium salicylate, calcium phenate, barium phenate, and the like. It is usually 0.1 to 10% by mass based on the total amount of the oil composition.
粘度指数向上剤としては、例えばポリメタクリレート系、ポリイソブテン系、エチレン−プロピレン共重合体系、スチレン−ブタジエン水添共重合体系のものなどが挙げられる。粘度指数向上剤の含有量は、潤滑油組成物全量を基準として、通常０．５〜３５質量％である。 Examples of the viscosity index improver include polymethacrylates, polyisobutenes, ethylene-propylene copolymer systems, and styrene-butadiene hydrogenated copolymer systems. The content of the viscosity index improver is usually 0.5 to 35% by mass based on the total amount of the lubricating oil composition.
本実施形態に係る潤滑油組成物の用途は特に制限されず、内燃機関用潤滑油、駆動系潤滑油等の幅広い分野で使用することができる。例えば、本実施形態に係る潤滑油組成物は、潤滑式（１）で表されるコハク酸イミド化合物を含有するため、従来のコハク酸イミド化合物と比較して、高い静摩擦係数（高い湿式摩擦材トルク容量）を達成することができ、自動変速機油や無段変速機油として好適である。また湿式クラッチ、湿式ブレーキを有する変速機を備えた建設機械や農機、手動変速機、二輪車ガソリンエンジン、ディーゼルエンジン、ガスエンジン、ショックアブソーバー油等の潤滑油として用いることができる。 The use of the lubricating oil composition according to the present embodiment is not particularly limited, and can be used in a wide range of fields such as a lubricating oil for internal combustion engines and a drive system lubricating oil. For example, since the lubricating oil composition according to the present embodiment contains a succinimide compound represented by the lubrication formula (1), it has a higher coefficient of static friction (high wet friction material) than a conventional succinimide compound. Torque capacity) and can be used as an automatic transmission oil or a continuously variable transmission oil. Further, it can be used as a lubricating oil for construction machines, agricultural machines, manual transmissions, two-wheeled gasoline engines, diesel engines, gas engines, shock absorber oils, etc., equipped with transmissions having wet clutches and wet brakes.
以下、実施例及び比較例に基づき本発明をさらに具体的に説明するが、本発明は以下の実施例に何ら限定されるものではない。 EXAMPLES Hereinafter, although this invention is demonstrated more concretely based on an Example and a comparative example, this invention is not limited to a following example at all.
［実施例１；コハク酸イミド化合物Ｉ−ａの合成］
合成装置を組み、１００ｍＬの４口フラスコに、Ｌ−チロシンエチルエステル（式（３）で表される化合物）１．０１ｇをはかりとり、４口フラスコ内を窒素置換した。
一方、１００ｍｌナスフラスコに、一般式（２）で表され、Ｒ１が数平均分子量１０００のポリイソブテニル基である化合物５．００ｇをはかりとり、それにキシレン４０ｍｌを加え、油浴で溶解させて溶液を得た。この溶液を、４口フラスコに装着した滴下ロートに移した。また、滴下を開始する前に４口フラスコ内に４０ｍｌのキシレンをロートを用いて加えた。上記の溶液を滴下ロートから滴下し、滴下終了後、３００ｒｐｍで撹拌しながら１６５℃で２４時間反応させた。
反応終了後、セライトろ過を行い、エバポレータにより溶媒を除去し、目的の生成物３．２１ｇを得た。
ＩＲ及びＧＰＣ分析により、得られた生成物が、一般式（１）で表され、Ｒ１が数平均分子量１０００のポリイソブテニル基であるコハク酸イミド化合物（以下、「コハク酸イミド化合物Ｉ−ａ」という。）であることを確認した。生成物のＩＲチャートを図１に示す。
Example 1 Synthesis of Succinimide Compound Ia
The synthesizer was assembled, 1.01 g of L-tyrosine ethyl ester (compound represented by formula (3)) was weighed into a 100 mL 4-neck flask, and the inside of the 4-neck flask was replaced with nitrogen.
On the other hand, in a 100 ml eggplant flask, weigh 5.00 g of a compound represented by the general formula (2) and R 1 is a polyisobutenyl group having a number average molecular weight of 1000, add 40 ml of xylene, dissolve in an oil bath, and dissolve the solution. Obtained. This solution was transferred to a dropping funnel attached to a four-necked flask. In addition, 40 ml of xylene was added into the four-necked flask using a funnel before the dropping was started. The above solution was dropped from the dropping funnel, and after completion of the dropping, the mixture was reacted at 165 ° C. for 24 hours while stirring at 300 rpm.
After completion of the reaction, the mixture was filtered through Celite, and the solvent was removed by an evaporator to obtain 3.21 g of the desired product.
The product obtained by IR and GPC analysis is represented by the general formula (1), and R 1 is a polyisobutenyl group having a number average molecular weight of 1000 (hereinafter referred to as “succinimide compound Ia”). It was confirmed that. An IR chart of the product is shown in FIG.
［実施例２；コハク酸イミド化合物Ｉ−ｂの合成］
合成装置を組み、１００ｍＬの４口フラスコに、Ｌ−チロシンエチルエステル（式（３）で表される化合物）０．４３ｇをはかりとり、４口フラスコ内を窒素置換した。
一方、１００ｍｌナスフラスコに、一般式（２）で表され、Ｒ１が数平均分子量２３００のポリイソブテニル基である化合物４．９８ｇをはかりとり、それにキシレン４０ｍｌを加え、油浴で溶解させて溶液を得た。この溶液を、４口フラスコに装着した滴下ロートに移した。また、滴下を開始する前に４口フラスコ内に４０ｍｌのキシレンをロートを用いて加えた。上記の溶液を滴下ロートから滴下し、滴下終了後、３００ｒｐｍで撹拌しながら１６５℃で２４時間反応させた。
反応終了後、セライトろ過を行い、エバポレータにより溶媒を除去し、目的の生成物５．３８ｇを得た。
ＩＲ及びＧＰＣ分析により、得られた生成物が、一般式（１）で表され、Ｒ１が数平均分子量２３００のポリイソブテニル基であるコハク酸イミド化合物（以下、「コハク酸イミド化合物Ｉ−ｂ」という。）であることを確認した。
[Example 2; Synthesis of succinimide compound Ib]
A synthesizer was assembled, 0.43 g of L-tyrosine ethyl ester (compound represented by formula (3)) was weighed into a 100 mL 4-neck flask, and the inside of the 4-neck flask was replaced with nitrogen.
On the other hand, in a 100 ml eggplant flask, 4.98 g of a compound represented by the general formula (2) and R 1 is a polyisobutenyl group having a number average molecular weight of 2300 is weighed, 40 ml of xylene is added thereto, and the solution is dissolved in an oil bath. Obtained. This solution was transferred to a dropping funnel attached to a four-necked flask. In addition, 40 ml of xylene was added into the four-necked flask using a funnel before the dropping was started. The above solution was dropped from the dropping funnel, and after completion of the dropping, the mixture was reacted at 165 ° C. for 24 hours while stirring at 300 rpm.
After completion of the reaction, the reaction mixture was filtered through Celite, and the solvent was removed by an evaporator to obtain 5.38 g of the desired product.
The product obtained by IR and GPC analysis is represented by the general formula (1), and R 1 is a polyisobutenyl group having a number average molecular weight of 2300 (hereinafter referred to as “succinimide compound Ib”). It was confirmed that.
［比較例１；コハク酸イミド化合物ＩＩの合成］
２０００ｍＬのオートクレーブに、ポリイソブテン（数平均分子量１０００）１．０ｍｏｌと、無水マレイン酸１．０ｍｏｌとを入れ、１．５時間かけて２２０℃まで昇温させ、２２０℃に達してから４時間反応させた。反応終了後、得られた生成物にｎ−ヘキサンを加え攪拌し、その液をろ過してスラッジを取り除いた。ろ液を常圧蒸留でｎ−ヘキサンを除去後、減圧下２２０℃で無水マレイン酸を除去し、マレイン化ポリイソブテンを得た。
２Ｌセパラブルフラスコに、ジエチレントリアミン１．７ｍｏｌ、キシレンを入れた。次に、キシレンに溶解させた得られたマレイン化ポリブテン０．１７ｍｏｌを滴下させながら、１４５〜１５５℃で１１時間反応させた。反応終了後、常圧蒸留で溶媒を除去し、減圧蒸留で残留ジエチレントリアミンを除去し、コハク酸イミド化合物ＩＩを得た。
[Comparative Example 1; Synthesis of Succinimide Compound II]
In a 2000 mL autoclave, 1.0 mol of polyisobutene (number average molecular weight 1000) and 1.0 mol of maleic anhydride are added, heated to 220 ° C. over 1.5 hours, and allowed to react for 4 hours after reaching 220 ° C. It was. After completion of the reaction, n-hexane was added to the obtained product and stirred, and the liquid was filtered to remove sludge. After removing n-hexane from the filtrate by atmospheric distillation, maleic anhydride was removed at 220 ° C. under reduced pressure to obtain maleated polyisobutene.
In a 2 L separable flask, 1.7 mol of diethylenetriamine and xylene were added. Next, it was made to react at 145-155 degreeC for 11 hours, dripping 0.17 mol of maleated polybutenes melt | dissolved in xylene. After completion of the reaction, the solvent was removed by atmospheric distillation, and residual diethylenetriamine was removed by distillation under reduced pressure to obtain succinimide compound II.
［実施例３〜８、比較例２〜４；潤滑油組成物の調製及び評価試験］
実施例３〜８においては、それぞれ、潤滑油基油としてのＳＡＥ１０留分（１００℃動粘度４．１ｍｍ２／ｓ）の鉱油、コハク酸イミド化合物Ｉ−ａ又はＩ−ｂ並びに以下に示す添加剤を用いて、表１に示す組成を有する潤滑油組成物を調製した。
比較例２、３においては、それぞれ、潤滑油基油としてのＳＡＥ１０留分（１００℃動粘度４．１ｍｍ２／ｓ）の鉱油、コハク酸イミド化合物ＩＩ並びに以下に示す添加剤を用いて、表２に示す組成を有する潤滑油組成物を調製した。また、比較例４においては、潤滑油基油としてのＳＡＥ１０留分（１００℃動粘度４．１ｍｍ２／ｓ）の鉱油及び以下に示す添加剤を用いて、表２に示す組成を有する潤滑油組成物を調製した。
ポリメタクリレート：平均分子量２０，０００
アミン系酸化防止剤：ジフェニルアミン
トリクレジルホスフェノート
カルシウムスルホネート：３００ＴＢＮ
無灰系油性剤：グリセリンモノオレート
[Examples 3-8, Comparative Examples 2-4; Preparation and Evaluation Test of Lubricating Oil Composition]
In Examples 3 to 8, mineral oil of 10 SAE fractions (100 ° C. kinematic viscosity 4.1 mm 2 / s) as a lubricating base oil, succinimide compound Ia or Ib, and additions shown below A lubricating oil composition having the composition shown in Table 1 was prepared using the agent.
In Comparative Examples 2 and 3, a mineral oil of SAE 10 fraction (100 ° C. kinematic viscosity 4.1 mm 2 / s) as a lubricant base oil, succinimide compound II, and the additives shown below were used, respectively. A lubricating oil composition having the composition shown in 2 was prepared. Further, in Comparative Example 4, a lubricating oil having the composition shown in Table 2 using a mineral oil of SAE 10 fraction (100 ° C. kinematic viscosity 4.1 mm 2 / s) as a lubricating base oil and the additives shown below. A composition was prepared.
Polymethacrylate: average molecular weight 20,000
Amine-based antioxidant: diphenylamine tricresyl phosphanote calcium sulfonate: 300TBN
Ashless oil-based agent: glycerol monooleate
次に、実施例３〜８及び比較例２〜４の潤滑油組成物について、ＬＦＷ−１試験機を用いて金属間摩擦係数を評価した。試験条件は面圧０．８ＧＰａ、すべり速度０．２ｍ／ｓ、試験温度８０℃で、試験時間１時間とし、時間内の摩擦係数を平均化した平均摩擦係数で評価した。得られた結果を表１〜２に示す。 Next, about the lubricating oil composition of Examples 3-8 and Comparative Examples 2-4, the friction coefficient between metals was evaluated using the LFW-1 test machine. The test conditions were a surface pressure of 0.8 GPa, a sliding speed of 0.2 m / s, a test temperature of 80 ° C., a test time of 1 hour, and an average friction coefficient obtained by averaging the friction coefficients within the time. The obtained result is shown to Tables 1-2.
本発明のコハク酸イミド化合物、潤滑油添加剤及び潤滑油組成物は、幅広い潤滑油分野で使用可能であり、特に、高い静摩擦係数が必要とされる自動変速機油や無段変速機油として好適である。 The succinimide compound, lubricating oil additive and lubricating oil composition of the present invention can be used in a wide range of lubricating oil fields, and are particularly suitable as automatic transmission oils and continuously variable transmission oils that require a high coefficient of static friction. is there.
Claims (5)
［式（１）中、Ｒ１は数平均分子量５００以上５０００未満のアルキル基又は数平均分子量５００以上５０００未満のアルケニル基を示す。］ A succinimide compound represented by the following general formula (1).
[In Formula (1), R 1 represents an alkyl group having a number average molecular weight of 500 or more and less than 5000 or an alkenyl group having a number average molecular weight of 500 or more and less than 5000. ]
［式（２）中、Ｒ１は数平均分子量５００以上５０００未満のアルキル基又は数平均分子量５００以上５０００未満のアルケニル基を示す。］
[In Formula (2), R 1 represents an alkyl group having a number average molecular weight of 500 or more and less than 5000 or an alkenyl group having a number average molecular weight of 500 or more and less than 5000. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012151824A JP2014015402A (en) | 2012-07-05 | 2012-07-05 | Succinimide compound, lubricating oil additive, and lubricating oil composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012151824A JP2014015402A (en) | 2012-07-05 | 2012-07-05 | Succinimide compound, lubricating oil additive, and lubricating oil composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2014015402A true JP2014015402A (en) | 2014-01-30 |
Family
ID=50110433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012151824A Pending JP2014015402A (en) | 2012-07-05 | 2012-07-05 | Succinimide compound, lubricating oil additive, and lubricating oil composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2014015402A (en) |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005146148A (en) * | 2003-11-17 | 2005-06-09 | Chevron Texaco Japan Ltd | Additive for lubricating oil and lubricating oil composition |
| JP2007238524A (en) * | 2006-03-09 | 2007-09-20 | Japan Science & Technology Agency | Method for producing monosubstituted succinimide |
| JP2010530470A (en) * | 2007-06-19 | 2010-09-09 | アフトン・ケミカル・コーポレーション | Pyrrolidine-2,5-dione derivatives for use in friction adjustment |
| JP2011208006A (en) * | 2010-03-30 | 2011-10-20 | Tachi S Co Ltd | Skin-integrated foamed molding |
| JP2011219536A (en) * | 2010-04-05 | 2011-11-04 | Jx Nippon Oil & Energy Corp | Succinimide compound, lubricant additive, and lubricant composition |
| JP2011219534A (en) * | 2010-04-05 | 2011-11-04 | Jx Nippon Oil & Energy Corp | Succinimide compound, lubricant additive, and lubricant composition |
| JP2011219537A (en) * | 2010-04-05 | 2011-11-04 | Jx Nippon Oil & Energy Corp | Succinimide compound, lubricant additive, and lubricant composition |
-
2012
- 2012-07-05 JP JP2012151824A patent/JP2014015402A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005146148A (en) * | 2003-11-17 | 2005-06-09 | Chevron Texaco Japan Ltd | Additive for lubricating oil and lubricating oil composition |
| JP2007238524A (en) * | 2006-03-09 | 2007-09-20 | Japan Science & Technology Agency | Method for producing monosubstituted succinimide |
| JP2010530470A (en) * | 2007-06-19 | 2010-09-09 | アフトン・ケミカル・コーポレーション | Pyrrolidine-2,5-dione derivatives for use in friction adjustment |
| JP2011208006A (en) * | 2010-03-30 | 2011-10-20 | Tachi S Co Ltd | Skin-integrated foamed molding |
| JP2011219536A (en) * | 2010-04-05 | 2011-11-04 | Jx Nippon Oil & Energy Corp | Succinimide compound, lubricant additive, and lubricant composition |
| JP2011219534A (en) * | 2010-04-05 | 2011-11-04 | Jx Nippon Oil & Energy Corp | Succinimide compound, lubricant additive, and lubricant composition |
| JP2011219537A (en) * | 2010-04-05 | 2011-11-04 | Jx Nippon Oil & Energy Corp | Succinimide compound, lubricant additive, and lubricant composition |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5504036B2 (en) | Friction modifier, lubricating oil additive and lubricating oil composition containing succinimide compound | |
| JP5315285B2 (en) | Succinimide compound, lubricating oil additive and lubricating oil composition | |
| JP5504033B2 (en) | Friction modifier, lubricating oil additive and lubricating oil composition containing succinimide compound | |
| WO2011122637A1 (en) | Succinimide compound, lubricating oil additive, and lubricating oil composition | |
| JP5315284B2 (en) | Succinimide compound, lubricating oil additive and lubricating oil composition | |
| JP5476192B2 (en) | Succinimide compound, lubricating oil additive and lubricating oil composition | |
| JP5543256B2 (en) | Succinimide compound, lubricating oil additive and lubricating oil composition | |
| JP5546316B2 (en) | Succinimide compound, lubricating oil additive and lubricating oil composition | |
| JP5504038B2 (en) | Friction modifier, lubricating oil additive and lubricating oil composition containing succinimide compound | |
| JP5889134B2 (en) | Succinimide compound, lubricating oil additive and lubricating oil composition | |
| JP5952659B2 (en) | Succinimide compound, lubricating oil additive and lubricating oil composition | |
| JP5876779B2 (en) | Succinimide compound, lubricating oil additive and lubricating oil composition | |
| JP5952661B2 (en) | Succinimide compound, lubricating oil additive and lubricating oil composition | |
| JP5829965B2 (en) | Succinimide compound, lubricating oil additive and lubricating oil composition | |
| JP2013203724A (en) | Succinimide compound, lubricating oil additive and lubricating oil composition | |
| WO2014007377A1 (en) | Succinimide compound, lubricating oil additive, and lubricating oil composition | |
| WO2014007379A1 (en) | Succinimide compound, lubricating oil additive, and lubricating oil composition | |
| JP5952658B2 (en) | Succinimide compound, lubricating oil additive and lubricating oil composition | |
| JP5952657B2 (en) | Succinimide compound, lubricating oil additive and lubricating oil composition | |
| JP5952660B2 (en) | Succinimide compound, lubricating oil additive and lubricating oil composition | |
| JP2014015495A (en) | Succinimide compound, lubricating oil additive, and lubricating oil composition | |
| JP6049282B2 (en) | Succinimide compound, lubricating oil additive and lubricating oil composition | |
| JP5504037B2 (en) | Friction modifier, lubricating oil additive and lubricating oil composition containing succinimide compound | |
| WO2014007378A1 (en) | Succinimide compound, lubricating oil additive, and lubricating oil composition | |
| JP2014015402A (en) | Succinimide compound, lubricating oil additive, and lubricating oil composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20150424 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20151126 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20151215 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20160301 |