JP5315285B2 - Succinimide compound, lubricating oil additive and lubricating oil composition - Google Patents
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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。） 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 (Patent Document 1 below). See ~ 3.)
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.
そこで本発明は、下記式（１）で表されるコハク酸イミド化合物を提供する。
［式（１）中、Ｒは数平均分子量５００以上５０００未満のアルキル基又はアルケニル基を示す。］
Therefore, the present invention provides a succinimide compound represented by the following formula (1).
[In the formula (1), R represents an alkyl group or 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 Patent Documents 1 to 3 above is used, a sufficient effect of improving friction characteristics cannot be obtained. In addition, in the case of the conventional succinimide compound, the cause is that the succinimide compound itself has an insufficient effect of improving the friction characteristics, and if the amount of succinimide is increased, the adsorptivity to the metal surface is increased. May change, and the balance of other additives may be lost, resulting in deterioration of friction characteristics.
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.
本発明のコハク酸イミド化合物において、式（１）中のＲは、数平均分子量５００以上５０００未満のポリイソブテンから誘導される基であることが好ましい。 In the succinimide compound of the present invention, R in the formula (1) is preferably a group derived from polyisobutene having a number average molecular weight of 500 or more and less than 5000.
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.
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.
［コハク酸イミド化合物］
本実施形態に係るコハク酸イミド化合物は、下記式（１）で表される構造を有する。
［式（１）中、Ｒは数平均分子量５００以上５０００未満のアルキル基又はアルケニル基を示す。］
[Succinimide compounds]
The succinimide compound according to the present embodiment has a structure represented by the following formula (1).
[In the formula (1), R represents an alkyl group or alkenyl group having a number average molecular weight of 500 or more and less than 5000. ]
式（１）中、Ｒで示されるアルキル基又はアルケニル基としては、ポリブテニル基、ポリイソブテニル基が好ましい。また、Ｒで示されるアルキル基又はアルケニル基の数平均分子量は、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。 In the formula (1), the alkyl group or alkenyl group represented by R is preferably a polybutenyl group or a polyisobutenyl group. The number average molecular weight of the alkyl group or alkenyl group represented by R is 500 or more and less than 5000, preferably 700 to 4000, more preferably 800 to 3500.
式（１）で表されるコハク酸イミド化合物は、数平均分子量５００以上５０００未満のアルキル基又はアルケニル基を有するマレイン化アルキル又はマレイン化アルケニルと、ヒスチジン（２−アミノ−３−（１Ｈ−イミダゾ−４−イル）プロピオン酸）とを反応させて得ることができる。また、原料として用いられる上記のマレイン化アルキル又はマレイン化アルケニルは、例えば数平均分子量５００以上５０００未満のポリアルケン（ポリブテン、ポリイソブテン等）と無水マレイン酸とを反応させて得ることができる。 The succinimide compound represented by the formula (1) includes a maleated alkyl or maleated alkenyl having an alkyl group or an alkenyl group having a number average molecular weight of 500 or more and less than 5000, and histidine (2-amino-3- (1H-imidazo It can be obtained by reacting -4-yl) propionic acid). The maleated alkyl or maleated alkenyl used as a raw material can be obtained, for example, by reacting a polyalkene (polybutene, polyisobutene, etc.) having a number average molecular weight of 500 or more and less than 5000 with maleic anhydride.
マレイン化アルキル又はマレイン化アルケニルと、ヒスチジンとを反応させるに際し、マレイン化アルキル又はマレイン化アルケニル／ヒスチジンの仕込み比は、モル比で、好ましくは１／１〜１／２、より好ましくは１／１〜１／１．８、さらに好ましくは１／１．１〜１／１．６、特に好ましくは１／１．２〜１／１．５とすることができる。上記範囲の割合で反応を行うことにより、目的のコハク酸イミド化合物をより確実に得ることができる。 When the maleated alkyl or maleated alkenyl is reacted with histidine, the charged ratio of maleated alkyl or maleated alkenyl / histidine is a molar ratio, preferably 1/1 to 1/2, more preferably 1/1. To 1 / 1.8, more preferably 1 / 1.1-1 / 1.6, and particularly preferably 1 / 1.2-1 / 1.5. By carrying out the reaction at a ratio in the above range, the objective succinimide compound can be obtained more reliably.
なお、上記の反応においては、式（１）で表されるコハク酸イミド化合物の他に、下記式（２）で表されるコハク酸イミド化合物が副生し得る。この場合、反応生成物から式（２）で表されるコハク酸イミド化合物を分離除去し、式（１）コハク酸イミド化合物のみを潤滑油添加剤としてもよく、あるいは、式（１）で表されるコハク酸イミド化合物と式（２）で表されるコハク酸イミド化合物との混合物を潤滑油添加剤として用いてもよい。
式（２）中、Ｒは数平均分子量５００以上５０００未満のアルキル基又はアルケニル基を示す。ｎは１以上の整数を示す。なお、ｎは通常１又は２であるが、合成の際に原料中のマレイン化アルキル又はマレイン化アルケニルに対するヒスチジンの割合が大きいと、ｎが増加する傾向にある。 In the formula (2), R represents an alkyl group or alkenyl group having a number average molecular weight of 500 or more and less than 5000. n represents an integer of 1 or more. Note that n is usually 1 or 2, but if the ratio of histidine to maleated alkyl or maleated alkenyl in the raw material during synthesis is large, n tends to increase.
また、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。 Further, the succinimide compound represented by the formula (1) may be used as it is without being boronated (that is, as a non-boronated 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、ホウ酸無水物およ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.
［潤滑油添加剤］
本実施形態に係る潤滑油添加剤は、上記式（１）で表され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、式（１）で表され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、式（１）で表され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。
[Lubricant additive]
The lubricating oil additive according to this embodiment contains a succinimide compound represented by the above formula (1). The lubricating oil additive may consist only of the succinimide compound represented by the formula (1), or may be a mixture of the succinimide compound represented by the formula (1) and other additives. There may be. The lubricating oil additive may further contain a diluent for dissolving the additive.
なお、式（１）で表され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ため、本実施形態に係る潤滑油添加剤が式（１）で表され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は特に制限されない。したがって、式（１）で表され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。 In addition, since the succinimide compound represented by the formula (1) is excellent in compatibility with various additives used in the lubricating oil field, the lubricant additive according to the present embodiment is represented by the formula (1). In the case of a mixture of the succinimide compound and other additives, the other additives used in combination are not particularly limited. Therefore, the kind of other additive used together with the succinimide compound represented by the formula (1) and the blending amount of both can be appropriately selected according to the use and purpose of the lubricating oil additive. Specific examples of other additives used in combination will be described later.
本実施形態に係る潤滑油組成物は、潤滑油基油と、上記式（１）で表され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。 The lubricating oil composition according to this embodiment contains a lubricating base oil and a succinimide compound represented by the above formula (1). In addition, the aspect containing the lubricating base oil and the lubricating oil additive which concerns on the said embodiment is included in the said lubricating oil composition.
潤滑油基油としては特に制限されず、鉱油およ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、溶剤精製また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また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 lubricating 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。 Moreover,% C A of the lubricating base oil, from the viewpoint of low temperature characteristics, it is more preferably preferably not more than 20, in particular 10 or less.
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、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、着色剤等に代表される各種添加剤をさらに含有することができる。これらの添加剤は、１種を単独で、または２種以上を組み合わせて用いることができる。 For the purpose of further improving the performance of the lubricating oil composition according to the present embodiment, an ashless dispersant and / or a friction modifier other than the succinimide compound represented by the formula (1), if necessary, a metal Various additives represented by system detergents, viscosity index improvers, extreme pressure additives, antioxidants, corrosion inhibitors, antifoaming agents, colorants and the like can be further contained. These additives can be used individually by 1 type or in combination of 2 or more types.
式（１）で表されるコハク酸イミド化合物以外の摩擦調整剤としては、脂肪酸エステル、脂肪酸アミド、または、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製剤などが挙げられ、これら中でも、リン化合物が好ましい。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。 Examples of the friction modifier other than the succinimide compound represented by the formula (1) include fatty acid esters, fatty acid amides, phosphorus compounds such as phosphate esters, phosphite esters, and thiophosphate esters, MoDTP, MoDTC, and the like. Examples include organomolybdenum compounds, organozinc compounds such as ZnDTP, organoboron compounds such as alkyl mercaptyl borates, solid lubricant friction modifiers such as graphite, molybdenum disulfide, antimony sulfide, boron compounds, and polytetrafluoroethylene. Of these, phosphorus compounds are preferred. The content of 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、その液をろ過して不溶解分を取り除いた。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。
一方、ヒスチジン０．００８ｍｏｌを乳鉢でつぶし、１００ｍＬ四口フラスコに入れ、キシレンを加えた。次に、キシレンに溶解させた得られたマレイン化ポリイソブテン０．００４ｍｏｌを滴下させながら、１６５℃で２４時間反応させた。反応終了後、ろ過で残留アミノ酸を除去し、減圧蒸留で溶媒を除去し、コハク酸イミド化合物Ｉを得た。得られたコハク酸イミド化合物Ｉについて赤外吸収スペクトルおよび元素分析を行い、式（１）で表される構造を有することを確認した。含有窒素は３．１８（理論値３．２１）％であった。
Example 1 Synthesis of Succinimide Compound I
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 solution was filtered to remove insoluble matter. After removing n-hexane from the filtrate by atmospheric distillation, maleic anhydride was removed at 220 ° C. under reduced pressure to obtain maleated polyisobutene.
On the other hand, 0.008 mol of histidine was crushed in a mortar, placed in a 100 mL four-necked flask, and xylene was added. Next, it was made to react at 165 degreeC for 24 hours, dripping 0.004 mol of maleated polyisobutenes obtained by making it melt | dissolve in xylene. After completion of the reaction, residual amino acid was removed by filtration, and the solvent was removed by distillation under reduced pressure to obtain succinimide compound I. The obtained succinimide compound I was subjected to infrared absorption spectrum and elemental analysis, and confirmed to have a structure represented by the formula (1). The nitrogen content was 3.18 (theoretical value 3.21)%.
［実施例２；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２３００）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、その液をろ過して不溶解分を取り除いた。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。
一方、ヒスチジン０．００８ｍｏｌを乳鉢でつぶし、１００ｍＬ四口フラスコに入れ、キシレンを加えた。次に、キシレンに溶解させた得られたマレイン化ポリイソブテン０．００４ｍｏｌを滴下させながら、１６５℃で２４時間反応させた。反応終了後、ろ過で残留アミノ酸を除去し、減圧蒸留で溶媒を除去し、コハク酸イミド化合物ＩＩを得た。得られたコハク酸イミド化合物ＩＩについて赤外吸収スペクトルおよび元素分析を行い、式（１）で表される構造を有することを確認した。含有窒素は１．５８（理論値１．６１）％であった。
[Example 2; Synthesis of succinimide compound II]
In a 2000 mL autoclave, 1.0 mol of polyisobutene (number average molecular weight 2300) 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 solution was filtered to remove insoluble matter. After removing n-hexane from the filtrate by atmospheric distillation, maleic anhydride was removed at 220 ° C. under reduced pressure to obtain maleated polyisobutene.
On the other hand, 0.008 mol of histidine was crushed in a mortar, placed in a 100 mL four-necked flask, and xylene was added. Next, it was made to react at 165 degreeC for 24 hours, dripping 0.004 mol of maleated polyisobutenes obtained by making it melt | dissolve in xylene. After completion of the reaction, residual amino acids were removed by filtration, and the solvent was removed by distillation under reduced pressure to obtain succinimide compound II. The obtained succinimide compound II was subjected to infrared absorption spectrum and elemental analysis, and confirmed to have a structure represented by the formula (1). The nitrogen content was 1.58 (theoretical value 1.61)%.
［比較例１；コハク酸イミド化合物ＩＩＩ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ＩＩＩを得た。
[Comparative Example 1; Synthesis of Succinimide Compound III]
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 III.
［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及び比較例２〜４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、ＩＩ又はＩＩＩ、並びに表１、２に示す添加剤を用いて、潤滑油組成物を調製した。各潤滑油組成物の組成を表１、２に示す。
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。
[Examples 3-8, Comparative Examples 2-4; Preparation and Evaluation Test of Lubricating Oil Composition]
In Examples 3 to 8 and Comparative Examples 2 to 4, mineral oil of SAE10 fraction (100 ° C. kinematic viscosity 4.1 mm 2 / s) as a lubricant base oil, succinimide compound I, II or III, A lubricating oil composition was prepared using the additives shown in Tables 1 and 2. The composition of each lubricating oil composition is shown in Tables 1 and 2.
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 results are shown in Tables 1 and 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断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. .
Claims (5)
［式（１）中、Ｒは数平均分子量５００以上５０００未満のアルキル基又はアルケニル基を示す。］ A succinimide compound represented by the following formula (1).
[In the formula (1), R represents an alkyl group or alkenyl group having a number average molecular weight of 500 or more and less than 5000. ]
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