JP2005539120A - Succinic acid semiamide as anticorrosive - Google Patents

Abstract

To provide succinic semiamide as an anticorrosive agent.
The present invention relates to an improved composition based on lubricants, including oxalic acid semiamide, and the properties of lubricants such as hydraulic fluids or metalworking fluids, greases, gear oils or engine oils. Of these lubricant compositions.

Description

  The present invention relates to compositions comprising oxalic acid semiamides and the use of those compositions in improving the performance of lubricants such as hydraulic fluids or metalworking fluids, greases, gear oils or engine oils.

Additives must be added to the lubricant that must meet stringent challenges such as high yield strength, protection against wear and corrosion, and antioxidant activity. Furthermore, the performance of the lubricant should not be detrimentally modified in the presence of contaminants. In the mineral oil industry, oil is often mixed with commercially available additive concentrates or 'packages'. Contamination with water, calcium detergent and other lubricant residues can occur during the mixing process. As a result, the function of the additive component with respect to corrosion is reduced, for example due to the formation of hydrolysis products and precipitation of poorly soluble calcium residues, and the latter is particularly disadvantageous because the residues block the filter system. It is.

  The present invention relates to the problem of manufacturing a lubricant composition that provides improved compatibility with corrosion as well as good compatibility with calcium ions.

  U.S. Pat. No. 4,462,918 discloses a lubricant composition that provides protection against wear and corrosion, comprising an N-acyl-N-alkylaminosuccinate type component (aspartate, aspartate). doing.

U.S. Pat. No. 5,275,749 discloses a lubricant composition which provides protection against wear and corrosion, consisting of components of the N-acyl-N-alkoxyalkylaminosuccinate type.
U.S. Pat. No. 4,462,918 US Pat. No. 5,275,749

  Surprisingly, the succinic semiamide obtained by reacting succinic anhydride with a β-amino acid derivative reduces the formation of precipitation products and residues while improving the corrosion protection in the lubricant composition. Has now been discovered.

［式中、
Ｒ₁は、炭素原子数１ないし２２のアルキル基、ヒドロキシ基で置換された炭素原子数
２ないし２２のアルキル基、−Ｃ（＝Ｏ）−、−Ｏ−Ｃ（＝Ｏ）−によって又は−ＮＲ_a−Ｃ（＝Ｏ）−によって中断された炭素原子数２ないし２２のアルキル基、−Ｏ−、−Ｓ−、−ＮＲ_a−、−Ｃ（＝Ｏ）−Ｏ−によって又は−Ｃ（＝Ｏ）−ＮＲ_a−によって中断された炭素原子数３ないし２２のアルキル基（式中、Ｒ_aは、水素原子又は炭素原子数１ないし２２のアルキル基を表わす。）、フェニル基、ベンジル基、１−又は２−フェニルエチル基、２−フェノキシエチル基、フルフリル基、１−ナフチル基、１−ナフチルメチル基、シクロヘキシル基、シクロヘキシルメチル基及びイソボルニル基からなる群から選択される置換基を表わし；
Ｒ₂及びＲ₃は水素原子を表わすか、又はＲ₂及びＲ₃の一方は水素原子を表わし、他方はメチル基を表わし；
Ｘは、カルボキシ基又はカルボキシレート基を表わし、Ｙ⁺は、潤滑剤組成物のために適当な塩形成性カチオンを表わすか；又は
Ｘは、シアノ基、炭素原子数１ないし２２のアルキル基でエステル化されたカルボキシ基、ヒドロキシ−炭素原子数２ないし２２のアルキル基でエステル化されたカルボキシ基、−Ｃ（＝Ｏ）−、−Ｃ（＝Ｏ）−Ｏ−によって又は−Ｃ（＝Ｏ）−ＮＲ_a−によって中断された炭素原子数２ないし２２のアルキル基でエステル化されたカルボキシ基、−Ｏ−、−Ｓ−、−ＮＲ_a−、−Ｏ−Ｃ（＝Ｏ）−によって又は−ＮＲ_a−（Ｃ＝Ｏ）−によって中断された炭素原子数３ないし２２のアルキル基でエステル化されたカルボキシ基（式中、Ｒ_aは、水素原子又は炭素原子数１ないし２２のアルキル基を表わす。）、フェニル基で、ベンジル基で、１−又は２−フェニルエチル基で、２−フェノキシエチル基で、フルフリル基で、１−ナフチル基で、１−ナフチルメチル基で、シクロヘキシル基で、シクロヘキシルメチル基で、イソボルニル基でエステル化されたカルボキシ基及び部分式

（式中、Ｒ_b及びＲ_cは、互いに独立して、水素原子、炭素原子数１ないし２２のアルキル基又は２−ヒドロキシエチル基を表わすか、又はＲ_b及びＲ_cは、一緒になって、炭素原子数２ないし８のアルキレン基、炭素原子数２ないし８のアルケニレン基、炭素原子数２ないし８のアルカジエニレン基、又は−Ｏ−によって又は−ＮＲ_a−によって中断された炭素原子数２ないし８のアルキレン基、炭素原子数２ないし８のアルケニレン基又は炭素原子数２ないし８のアルカジエニレン基を表わし、Ｒ_aは上記で定義した通りである。）で表わされるカルバモイル基からなる群から選択された誘導体化カルボキシ基を表わし；及び、
Ｙ⁺は、水素イオンを表わすか、又は潤滑剤組成物のために適当な塩形成性カチオンを表わす。］で表わされる化合物；及び、
ｂ）潤滑粘度の基油
からなる組成物に関する。 The present invention
a) at least one formula

[Where:
R ₁ represents an alkyl group having 1 to 22 carbon atoms, an alkyl group having 2 to 22 carbon atoms substituted with a hydroxy group, —C (═O) —, —O—C (═O) —, or — C 2 -C 22 alkyl group interrupted by NR _a —C (═O) —, —O—, —S—, —NR _a —, —C (═O) —O— or —C ( ═O) an alkyl group having 3 to 22 carbon atoms interrupted by —NR _a — (wherein R _a represents a hydrogen atom or an alkyl group having 1 to 22 carbon atoms), phenyl group, benzyl group Represents a substituent selected from the group consisting of 1- or 2-phenylethyl group, 2-phenoxyethyl group, furfuryl group, 1-naphthyl group, 1-naphthylmethyl group, cyclohexyl group, cyclohexylmethyl group and isobornyl group. ;
R ₂ and R ₃ represent a hydrogen atom, or one of R ₂ and R ₃ represents a hydrogen atom and the other represents a methyl group;
X represents a carboxy group or a carboxylate group and Y ⁺ represents a salt-forming cation suitable for the lubricant composition; or X is a cyano group, an alkyl group having 1 to 22 carbon atoms Esterified carboxy group, hydroxy-carboxy group esterified with an alkyl group having 2 to 22 carbon atoms, -C (= O)-, -C (= O) -O-, or -C (= O ) -NR _a - carboxy esterified with alkyl of 2 carbon atoms which is interrupted 22 by, -O -, - S -, - NR a -, - O-C (= O) - or by Carboxyl group esterified with an alkyl group having 3 to 22 carbon atoms interrupted by —NR _a — (C═O) — (wherein R _a is a hydrogen atom or an alkyl group having 1 to 22 carbon atoms) Represents) An benzyl group, a benzyl group, a 1- or 2-phenylethyl group, a 2-phenoxyethyl group, a furfuryl group, a 1-naphthyl group, a 1-naphthylmethyl group, a cyclohexyl group, a cyclohexylmethyl group A carboxy group esterified with an isobornyl group and a partial formula

(Wherein R _b and R _c each independently represent a hydrogen atom, an alkyl group having 1 to 22 carbon atoms, or a 2-hydroxyethyl group, or R _b and R _c are taken together) An alkylene group having 2 to 8 carbon atoms, an alkenylene group having 2 to 8 carbon atoms, an alkadienylene group having 2 to 8 carbon atoms, or 2 to 8 carbon atoms interrupted by —O— or by —NR _a —. Represents an alkylene group having 8 carbon atoms, an alkenylene group having 2 to 8 carbon atoms, or an alkadienylene group having 2 to 8 carbon atoms, and R _a is as defined above. Represents a derivatized carboxy group; and
Y ⁺ represents a hydrogen ion or a salt forming cation suitable for a lubricant composition. And a compound represented by:
b) relates to a composition comprising a base oil of lubricating viscosity.

  Compound (I) has an excellent anticorrosion function with good compatibility with calcium ions, and it can be present in lubricants, in particular as a constituent of detergents.

Preferred embodiments are:
a) at least one compound (I)
[Where:
R ₁ represents an alkyl group having 1 to 22 carbon atoms, an alkyl group having 2 to 22 carbon atoms substituted with a hydroxy group, —C (═O) —, —O—C (═O) —, or — C 2 -C 22 alkyl group interrupted by NR _a —C (═O) —, —O—, —S—, —NR _a —, —C (═O) —O— or —C ( ═O) an alkyl group having 3 to 22 carbon atoms interrupted by —NR _a — (wherein R _a represents a hydrogen atom or an alkyl group having 1 to 22 carbon atoms), phenyl group, benzyl group Represents a substituent selected from the group consisting of 1- or 2-phenylethyl group, 2-phenoxyethyl group, furfuryl group, 1-naphthyl group, 1-naphthylmethyl group, cyclohexyl group, cyclohexylmethyl group and isobornyl group. ;
R ₂ and R ₃ represent a hydrogen atom, or one of R ₂ and R ₃ represents a hydrogen atom and the other represents a methyl group;
X represents a cyano group, a carboxy group esterified with an alkyl group having 1 to 22 carbon atoms, a carboxy group esterified with a hydroxy-alkyl group having 2 to 22 carbon atoms, -C (= O)-, A carboxyl group esterified with an alkyl group of 2 to 22 carbon atoms interrupted by —C (═O) —O— or —C (═O) —NR _a —, —O—, —S—, _{-NR a -, - O-C} (= O) - or by _{-NR a - (C = O)} - a carboxyl group esterified with an alkyl group having 3 to carbon atoms which is interrupted 22 by (wherein, R _a represents a hydrogen atom or an alkyl group having 1 to 22 carbon atoms), a phenyl group, a benzyl group, a 1- or 2-phenylethyl group, a 2-phenoxyethyl group, a furfuryl group, 1-naphthyl group , 1 in naphthylmethyl group, cyclohexyl group, cyclohexyl methyl group, a carboxyl group esterified and subexpressions isobornyl group (A) (wherein, R _b and R _c are independently of each other, hydrogen atom Represents an alkyl group having 1 to 22 carbon atoms or a 2-hydroxyethyl group, or R _b and R _c together represent an alkylene group having 2 to 8 carbon atoms, a group having 2 to 8 carbon atoms, An alkenylene group, an alkadienylene group having 2 to 8 carbon atoms, or an alkylene group having 2 to 8 carbon atoms interrupted by —O— or by —NR _a —, an alkenylene group having 2 to 8 carbon atoms or the number of carbon atoms 2 to represent alkadienylene group 8, R _a is selected from the group consisting of carbamoyl group represented by are as defined above.) induction It represents a reduction carboxy group; and,
Y ⁺ represents a hydrogen ion or a salt forming cation suitable for a lubricant composition. ];as well as,
b) relates to a composition comprising a base oil of lubricating viscosity.

Particularly preferred embodiments are:
a) at least one compound (I)
(Where
R ₁ is an alkyl group having 1 to 22 carbon atoms, —C (═O) — or an alkyl group having 2 to 22 carbon atoms interrupted by —O—C (═O) —, —O— Represents a substituent selected from the group consisting of an alkyl group having 3 to 22 carbon atoms, a phenyl group and a benzyl group interrupted by -S- or by -C (= O) -O-;
R ₂ and R ₃ represent a hydrogen atom;
X is a cyano group, a carboxy group esterified with an alkyl group having 1 to 22 carbon atoms, a carboxy group esterified with a hydroxy-alkyl group having 2 to 22 carbon atoms, or -C (= O)-. Or a carboxy group esterified with an alkyl group of 2 to 22 carbon atoms interrupted by —C (═O) —O—, by —O—, —S— or by —O— (C═O) —. A derivatized carboxy group selected from the group consisting of an interrupted carboxy group esterified with an alkyl group having 3 to 22 carbon atoms and a carbamoyl group represented by the partial formula (A) defined as a heterocyclic carbonyl group And; and
Y ⁺ represents a hydrogen ion, ammonium, (alkyl having 1 to 4 carbon atoms) _{1 to 4} ammonium or (2-hydroxyethyl) _{1 to 4} ammonium. );as well as,
b) A composition comprising a base oil of lubricating viscosity.

A very particularly preferred embodiment is
a) at least one compound (I)
(Where
R ₁ represents a substituent selected from the group consisting of an alkyl group having 1 to 22 carbon atoms, an alkyl group having 3 to 22 carbon atoms interrupted by —O—, a phenyl group, and a benzyl group;
R ₂ and R ₃ represent a hydrogen atom;
X is a cyano group, a carboxy group esterified with an alkyl group having 1 to 22 carbon atoms, a carboxy group esterified with an alkyl group having 3 to 22 carbon atoms interrupted by —O—, and piperidyl Represents a derivatized carboxy group selected from the group consisting of a carbamoyl group represented by the partial formula (A) defined as a nocarbonyl group, a piperazinylcarbonyl group or a morpholinocarbonyl group; and
Y ⁺ represents a hydrogen ion, ammonium, (alkyl having 1 to 4 carbon atoms) _{1 to 4} ammonium or (2-hydroxyethyl) _{1 to 4} ammonium. );as well as,
b) relates to a composition comprising a base oil of lubricating viscosity.

Similarly, a very particularly preferred embodiment is
a) at least one compound (I)
(Where
R ₁ represents a substituent selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an alkyl group having 3 to 18 carbon atoms interrupted by —O—, a phenyl group, and a benzyl group;
R ₂ and R ₃ represent a hydrogen atom;
X represents a carboxy group and Y represents ammonium, (alkyl of ₁ to 4 carbon atoms) _{1 to 4} ammonium or (2-hydroxyethyl) _{1 to 4} ammonium; or
X represents a carboxylate group, or esterified with a cyano group, a carboxy group esterified with an alkyl group having 1 to 18 carbon atoms, or an alkyl group with 3 to 18 carbon atoms interrupted by —O— Represents a derivatized carboxy group selected from the group consisting of a selected carboxy group and a morpholinocarbamoyl group; and
Y represents a hydrogen atom, ammonium, (alkyl having 1 to 4 carbon atoms) _{1 to 4} ammonium or (2-hydroxyethyl) _{1 to 4} ammonium. );as well as,
b) relates to a composition comprising a base oil of lubricating viscosity.

へ添加（α，β−不飽和カルボニル化合物へのアミンの添加）し、β−アミノ酸誘導体

を形成し、そしてそれを琥珀酸の反応性の官能性誘導体、例えば、無水琥珀酸又は琥珀酸モノクロリドでアシル化することによって製造される。 Compound (I), in a manner known per se, for example, a primary amine R ₁ -NH ₂ acrylic acid derivative

(Addition of amine to α, β-unsaturated carbonyl compound) and β-amino acid derivative

And is acylated with a reactive functional derivative of succinic acid such as succinic anhydride or succinic acid monochloride.

  German Offenlegungsschrift 2054649 describes the addition of primary amines to acrylate esters and subsequent reaction with succinic anhydride. The compounds described there can be used inter alia as fiber auxiliaries.

The terms and general names used in the description of the present invention are preferably defined as follows:
Component a) Compound (I)
R ₁ and R _a , defined as alkyl groups having 1 to 22 carbon atoms, include saturated, unbranched or possibly branched hydrocarbon groups, especially alkyl groups having 1 to 9 carbon atoms. For example, methyl group, ethyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, neopentyl group, isopentyl group, n-hexyl group, 2-ethylbutyl group, 1-methylpentyl Group, 1,3-di-methylbutyl group, n-heptyl group, 3-heptyl group, 1-methylhexyl group, isoheptyl group, n-octyl group, 2-ethylhexyl group, 1,1,3,3-tetramethyl A butyl group, a 1-methylheptyl group, an n-nonyl group or a 1,1,3-trimethylhexyl group, and also an alkyl group having 10 to 22 carbon atoms, An alkyl group having 10 to 22 carbon atoms in the chain, for example, n-decyl group, n-dodecyl group, n-tetradecyl group, n-hexadecyl group or n-octadecyl group, or branched alkyl group having 10 to 22 carbon atoms Groups such as 1,1,3-trimethylhexyl, 1-methylundecyl, 2-n-butyl-n-octyl, isotridecyl, 2-n-hexyl-n-decyl or 2-n- It contains an octyl-n-dodecyl group, or a higher homologue thereof.

R ₁ defined as an alkyl group having 2 to 22 carbon atoms substituted with a hydroxy group is preferably a saturated, unbranched hydrocarbon group having 2 to 9 carbon atoms, for example 2-hydroxy Contains an ethyl group or a 2- or 3-hydroxypropyl group.

R ₁ defined as an alkyl group having 2 to 22 carbon atoms interrupted by —C (═O) —, —O—C (═O) — or —NR _a —C (═O) — Preferably an unbranched or branched hydrocarbon group having 2 to 9 carbon atoms, for example an acetyl group, an acetoxycarbonylmethyl group, a 2-acetoxycarbonylethyl group, a 2-tert-butoxycarbonylethyl group or N, Contains an N-diethylcarbamoyl group.

-O -, - S -, - NR a -, - C (= O) -O- or by -C (= O) -NR _a - is defined as an alkyl group having 3 to carbon atoms which is interrupted 22 by R ₁ is preferably an unbranched or branched hydrocarbon group having 3 to 18 carbon atoms, such as a 2-methoxyethyl group, 2- or 3-methoxypropyl group, 2-, 3- or 4-methoxybutyl group, 2-ethoxyethyl group, 2- or 3-ethoxypropyl group, 2-, 3- or 4-ethoxybutyl group, 2-n-propoxyethyl group, 2- or 3-n-propoxypropyl Group, 2-, 3- or 4-n-propoxybutyl group, 2-isopropoxyethyl group, 2- or 3-isopropoxypropyl group, 2-, 3- or 4-isopropoxybutyl group, 2-n- Butoxye 2-, 3-n-butoxypropyl group, 2-, 3- or 4-n-butoxybutyl group, 2-tert-butoxyethyl group, 2- or 3-tert-butoxypropyl group, 2-, 3- or 4-tert-butoxybutyl group, 2-methylthioethyl group, 2- or 3-methylthiopropyl group, 2-ethylthioethyl group, 2-dimethylaminoethyl group, 2- or 3-dimethylaminopropyl group, 2-diethylaminoethyl group, 2- or 3-diethylaminopropyl group, 2-acetoxyethyl group or 2- (N-acetoxy-N-methyl) -ethyl group.

In the compound (I), R ₂ and R ₃ represent a hydrogen atom, or one of R ₂ and R ₃ represents a hydrogen atom and the other represents a methyl group. Preferably, R ₂ and R ₃ represent a hydrogen atom.

In compound (I), when X represents a carboxy group or a carboxylate [—C (═O) —O ⁻ ], Y ⁺ represents a salt-forming cation suitable for the lubricant composition, such as ammonium, tetra Represents methylammonium, tetraethylammonium or 2-hydroxyethyltrimethylammonium. In the substantially undissociated form [—C (═O) —OH] or, for example, the salt form with ammonium ions such as ammonium, tetramethylammonium, tetraethylammonium or 2-hydroxyethyltrimethylammonium [—C (= O) —O ⁻ ] only one carboxy group is present.

In a preferred embodiment, X represents a derivatized carboxy group as defined below or an unsubstituted or substituted carbamoyl group. In that case, Y ⁺ represents a hydrogen ion or a salt-forming cation suitable for the lubricant composition.

X defined as a carboxy group esterified by an alkyl group having 1 to 22 carbon atoms is, for example, an alkyl group having 1 to 22 carbon atoms as defined above for R ₁ , eg, saturated, branched A branched hydrocarbon group such as methyl, ethyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, isopentyl, n -Hexyl group, 2-ethylbutyl group, 1-methylpentyl group, 1,3-di-methylbutyl group, n-heptyl group, 3-heptyl group, 1-methylhexyl group, isoheptyl group, n-octyl group, 2- Ethylhexyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, n-nonyl or 1,1,3-trimethyl By syl groups and also alkyl groups having 10 to 22 carbon atoms, in particular linear alkyl groups having 10 to 22 carbon atoms, such as n-decyl group, n-dodecyl group, n-tetradecyl group, n- It represents a carboxy group esterified with a hexadecyl group or an n-octadecyl group.

X, defined as a carboxy group esterified by a hydroxy-C2-C22 alkyl group, for example, a hydroxy-C2-C22 alkyl group as defined above for R < ₁ >, e.g. It represents a carboxy group esterified with a 2-hydroxyethoxycarbonyl group or a 2- or 3-hydroxypropoxycarbonyl group.

As a carboxy group esterified with an alkyl group of 2 to 22 carbon atoms interrupted by —C (═O) —, —C (═O) —O— or by —C (═O) —NR _a —. X as defined is for example carbon as defined above for R ₁ interrupted by —C (═O) —, —C (═O) —O— or —C (═O) —NR _a —. A carboxy group esterified with an alkyl group having 2 to 22 atoms, for example, an acetyloxycarbonyl group, an acetoxycarbonylmethoxycarbonyl group or a 2-acetoxycarbonylethoxycarbonyl group.

Esterification with alkyl groups of 3 to 22 carbon atoms interrupted by —O—, —S—, —NR _a —, —O—C (═O) — or by —NR _a — (C═O) —. X defined as a defined carboxy group is interrupted, for example, by —O—, —S—, —NR _a —, —O—C (═O) — or by —NR _a — (C═O) —. A carboxy group esterified by an alkyl group having 3 to 22 carbon atoms (as defined above for R ₁ ), such as a 2-methoxyethoxycarbonyl group, a 2- or 3-methoxypropoxycarbonyl group, 2- , 3- or 4-methoxybutoxycarbonyl group, 2-ethoxyethoxycarbonyl group, 2
-Or 3-ethoxypropoxycarbonyl group, 2-, 3- or 4-ethoxybutoxycarbonyl group, 2-methylthioethoxycarbonyl group, 2- or 3-methylthiopropoxycarbonyl group, 2-ethylthioethoxycarbonyl group, 2-dimethyl Aminoethoxycarbonyl group, 2- or 3-dimethylaminopropoxycarbonyl group, 2-diethylaminoethoxycarbonyl group, 2- or 3-diethylaminopropoxycarbonyl group, 2-acetoxyethoxycarbonyl group or 2- (N-acetoxy-N-methyl) ) Represents an ethoxycarbonyl group.

X defined as the carbamoyl group represented by the partial formula A represents, for example, a carbamoyl group, a dimethyl- or a diethyl-carbamoyl group. Further, R _b and R _c are each an alkylene group having 2 to 8 carbon atoms, such as a 1,4-n-butylene group or a 1,5-n-pentylene group, and an alkenylene group having 2 to 8 carbon atoms, For example, it can be linked together by a 2-butenylene group or by an alkadienylene group having 2 to 8 carbon atoms, for example a 1,3-butadienylene group, and together with -N <, a further heteroatom, for example Heterocycles that may contain N or O are formed. In this case, partial formula A corresponds to a heterocyclic carbonyl substituent, for example a piperidinocarbonyl group, a piperazinylcarbonyl group or a morpholinocarbonyl group.

In the compound (I), the total number of carbon atoms present in R ₁ and X is preferably greater than 10.

The definition used in Y ⁺ , “salt-forming cation suitable for lubricant compositions” is a metal salt suitable for lubricant compositions together with carboxylate groups, such as alkali Cations of salt formers that form metal salts, alkaline earth metal salts, zinc (Zn ²⁺ ) or copper (Cu ²⁺ ) salts, such as sodium ions, potassium ions, calcium ions, Zn ²⁺ ions are Cu ^{2 +} Contains ions.

In a preferred embodiment of the present invention, the definition used in Y ⁺ , 'a salt-forming cation suitable for a lubricant composition' is a salt that together with the carboxylate group forms a suitable non-metal salt. Forming cations, such as ammonium, (alkyl of 1 to 22 carbon atoms) _{1 to 4} ammonium or (2-hydroxyethyl) _{1 to 4} ammonium, such as tetramethylammonium, tetraethylammonium or 2-hydroxyethyltrimethylammonium Is understood to mean.

  Compound (I) is readily soluble in oil and can be mixed in a known manner with a base oil of lubricating viscosity, such as a lubricant.

Component b) Base oil The definition "base oil of lubricating viscosity" includes, for example, a lubricant that can be used in hydraulic fluids or metalworking fluids, greases, gear oils or engine oils.

Suitable lubricants are based, for example, on mineral or synthetic oils or mixtures thereof. Lubricants are well known to those skilled in the art and are described in the relevant technical literature such as Chemistry and Technology of Lubricants; M.M. And Ausuriku, S .; T.A. (Editor); 1992, UK, Blackie and Sun, USA, New York VCH-Publisher, ISBN 0-216-92921-0 (see pages 208 to 269); Kirk-Othmer Engineering of Chemical Technology, 4th edition 1969, J. Am. Willie & Sun, New York, Vol. 13, 533 (pressure fluid); Performance Testing of Hydrodynamic Fluids, R.C. Tourlet and E.E. P. Wright, for the London Petroleum Association, UK, Hayden & Sun, ISBN 0 85501 317 6; Ullmann's Encyclopaedia of Ind. Chem. , Fifth Revised Edition, Barrag Chemi, Germany, Wayne Heim, USA, VCH-Publisher, A15, 423 (lubricant), A13, 165 (pressure fluid). .

  Lubricants are in particular oils and greases based on, for example, mineral or vegetable oils and animal oils, greases, tallows and waxes, or mixtures thereof. Vegetable oil and animal oil, grease, tallow and wax are, for example, palm seed oil, palm oil, olive oil, rapeseed oil, rape oil, linseed oil, soybean oil, cottonseed oil, sunflower oil, coconut oil, Corn oil, castor oil, nut oil and mixtures thereof, fish oil, and their chemically modified forms, such as epoxidized and sulfoxylated forms, or forms produced by genetic engineering, such as genetic engineering Soybean oil.

  Examples of synthetic lubricants are aliphatic or aromatic carboxylic esters, polymeric esters, polyalkylene oxides, phosphate esters, poly-α-olefins or silicones, diesters of diacids and monohydric alcohols, for example dioctyl. Triesters of trimethylolpropane and monovalent acids or mixtures of such acids, such as sebacate or dinonyl adipate, such as trimethylolpropane triperagonate, trimethylolpropane tricaprylate or mixtures thereof, penta Tetraesters of erythritol and monohydric acids or mixtures of such acids, such as pentaerythritol tetracaprylate, etc., or complex esters of mono- and dihydric acids and polyhydric alcohols, such as trimethylolpropane and caprylic acid and sebacine A complex ester of an acid, or Including a lubricant based on a mixture of these. Apart from mineral oils, for example, poly-α-olefins, ester-based lubricants, phosphates, glycols, polyglycols and polyalkylene glycols, and also mixtures thereof with water are particularly suitable.

  Organic or inorganic thickeners can also be added to the lubricant or mixtures thereof (base grease). Metalworking fluids and hydraulic fluids can be manufactured based on materials similar to those described above for the lubricant. Such liquids are also often emulsions of such substances in water or other liquids.

  The composition advantageously comprises 0.005 to 10.0% by weight, preferably 0.01 to 5.0% by weight, in particular 0.01 to 0.9% by weight of component (I).

  The composition is used, for example, in hydraulic fluids or metalworking fluids, greases, gear oils or oils for Otto, Diesel, Two-stroke, Wankel or Orbital type engines.

  The lubricants can further include other additives added to further improve their basic properties; such additives include antioxidants, metal deactivators, rust inhibitors, viscosities. Includes index improvers, pour point depressants, dispersants, detergents, extreme pressure additives, antiwear additives, and friction reducers. Such additives are added in conventional amounts in each case in the range of about 0.01 to 10.0% by weight. Examples of further additives are shown below.

Phenolic antioxidant
1. Alkylated monophenols : 2,6-di-tert-butyl-4-methylphenol, 2-butyl-4,6-di-methylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2, 6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-iso-butylphenol, 2,6-dicyclopentyl-4-methylphenol, 2-
(Α-methylcyclohexyl) -4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethyl Phenol, linear nonylphenol or nonylphenol branched in the side chain, for example 2,6-di-nonyl-4-methylphenol, 2,4-dimethyl-6- (1'-methylundec-1'-yl) phenol 2,4-dimethyl-6- (1'-methylheptadec-1'-yl) phenol, 2,4-dimethyl-6- (1'-methyltridec-1'-yl) phenol and mixtures thereof.
2. Alkylthiomethylphenol : 2,4-di-octylthiomethyl-6-tert-butylphenol, 2,4-di-octylthiomethyl-6-methylphenol, 2,4-di-octylthiomethyl-6-ethylphenol, 2,6-di-dodecylthiomethyl-4-nonylphenol.
3. Hydroquinone and alkylated hydroquinone : 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4 Octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5- Di-tert-butyl-4-hydroxyphenyl stearate, bis (3,5-di-tert-butyl-4-hydroxyphenyl) adipate.
4). Tocopherol : α-, β-, γ- and δ-tocopherol or mixtures thereof (vitamin E).
5. Hydroxylated thiodiphenyl ether : 2,2′-thiobis (6-tert-butyl-4-methylphenol), 2,2′-thiobis (4-octylphenol), 4,4′-thiobis (6-tert-butyl-3) -Methylphenol), 4,4'-thiobis (6-tert-butyl-2-methylphenol), 4,4'-thiobis (3,6-di-secondary amylphenol), 4,4'-bis ( 2,6-di-methyl-4-hydroxyphenyl) disulfide.
6). Alkylidene bisphenol : 2,2′-methylene bis (6-tert-butyl-4-methylphenol), 2,2′-methylene bis (6-tert-butyl-4-ethylphenol), 2,2′-methylene bis [4- Methyl-6- (α-methylcyclohexyl) phenol], 2,2′-methylenebis (4-methyl-6-cyclohexylphenol), 2,2′-methylenebis (6-nonyl-4-methylphenol), 2,2 '-Methylenebis (4,6-di-tert-butylphenol), 2,2'-ethylidenebis (4,6-di-tert-butylphenol), 2,2'-ethylidenebis (6-tert-butyl-4- Isobutylphenol), 2,2′-methylenebis [6- (α-methylbenzyl) -4-nonylphenol], 2,2′-methylene-bis [6- (α, α-dimethyl) Nyl) -4-nonylphenol], 4,4′-methylenebis (2,6-di-tert-butylphenol), 4,4′-methylenebis (6-tert-butyl-2-methylphenol), 1,1-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 2,6-bis (3-tert-butyl-5-methyl-2-hydroxybenzyl) -4-methylphenol, 1,1,3 -Tris (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 1,1-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) -3-n-dodecyl mercaptobutane, Ethylene glycol bis [3,3-bis (3′-tert-butyl-4′-hydroxyphenyl) butyrate], bis (3-tert-butyl-4-hydroxy-5-methylphenyl) dicyclo-pe Tadiene, bis [2- (3′-tert-butyl-2′-hydroxy-5′-methylbenzyl) -6-tert-butyl-4-methylphenyl] terephthalate, 1,1-bis- (3,5- Dimethyl-2-hydroxyphenyl) butane, 2,2-bis (3,5-di-tert-butyl-4-hydroxyphenyl) propane, 2,2-bis- (5-tert-butyl-4-hydroxy-2-) Methylphenyl) -4-n-dodecylmercaptobutane, 1,1,5,5-tetra (5-tert-butyl-4-hydroxy-2-methylphenyl) pentane.
7). O-, N- and S-benzyl compounds : 3,5,3 ', 5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-
Dimethylbenzyl mercaptoacetate, tridecyl-4-hydroxy-3,5-di-tert-butylbenzyl mercaptoacetate, tris (3,5-di-tert-butyl-4-hydroxybenzyl) amine, bis (4-tert-butyl) -3-hydroxy-2,6-dimethylbenzyl) dithioterephthalate, bis (3,5-di-tert-butyl-4-hydroxybenzyl) sulfide, isooctyl-3,5-di-tert-butyl-4-hydroxybenzyl Mercaptoacetate.
8). Hydroxybenzylated malonate : dioctadecyl 2,2-bis (3,5-di-tert-butyl-2-hydroxybenzyl) malonate, di-octadecyl 2- (3-tert-butyl-4-hydroxy-5-methylbenzyl ) -Malonate, di-dodecyl mercaptoethyl-2,2-bis (3,5-di-tert-butyl-4-hydroxybenzyl) -malonate or di [4- (1,1,3,3-tetramethylbutyl) ) Phenyl] 2,2-bis (3,5-di-tert-butyl-4-hydroxybenzyl) malonate.
9. Hydroxybenzyl aromatic compounds : 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -2,4,6-trimethylbenzene, 1,4-bis (3,5-di -Tert-butyl-4-hydroxybenzyl) -2,3,5,6-tetramethylbenzene, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) phenol.
10. Triazine compound : 2,4-bisoctyl mercapto-6- (3,5-di-tert-butyl-4-hydroxyanilino) -1,3,5-triazine, 2-octyl mercapto-4,6-bis ( 3,5-di-tert-butyl-4-hydroxyanilino) -1,3,5-triazine, 2-octyl mercapto-4,6-bis (3,5-di-tert-butyl-4-hydroxyphenoxy) ) -1,3,5-triazine, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxyphenoxy) -1,2,3-triazine, 1,3,5-tris ( 3,5-di-tert-butyl-4-hydroxybenzyl) -isocyanurate, 1,3,5-tris (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, 2,4 , 6-Tris- (3,5- -Tert-butyl-4-hydroxyphenylethyl) -1,3,5-triazine, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hexahydro-1,3 5-Triazine, 1,3,5-tris (3,5-dicyclohexyl-4-hydroxybenzyl) isocyanurate.
11. Acylaminophenol : 4-hydroxylauric acid anilide, 4-hydroxysteric acid anilide, N- (3,5-di-tert-butyl-4-hydroxyphenyl) carbamic acid octyl ester.
12 β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid , mono- or polyhydric alcohols such as methanol, ethanol, n-octanol, isooctanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) succinic acid diamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxavic [2.2.2] octane.
13. Esters of β- (5-tert-butyl-4-hydroxy-3-methylphenyl) propionic acid (and mono- or polyhydric alcohols) : for example, methanol, ethanol, n-octanol, isooctanol, octadecanol, 1 , 6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N '-Bis (hydroxyethyl) succinic acid diamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabici (B) [2.2.2] octane.
14 β- (3,5-dicyclohexyl-4-hydroxyphenyl) propionic acid ester , mono- or polyhydric alcohols such as 13. Esters with alcohols mentioned in.
15. Esters of 3,5-di-tert-butyl-4-hydroxyphenylacetic acid , which are mono- or polyhydric alcohols, for example 13. Esters with alcohols mentioned in.
16. Amides of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid , such as N, N′-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hexamethylene Diamine, N, N′-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) trimethylenediamine, N, N′-bis (3,5-di-tert-butyl-4-hydroxyphenyl) Propionyl) hydrazide.

Amine type antioxidants N, N'-di-isopropyl-p-phenylenediamine, N, N'-di-secondary butyl-p-phenylenediamine, N, N'-bis (1,4-dimethylpentyl)- p-phenylenediamine, N, N′-bis (1-ethyl-3-methyl-pentyl) -p-phenylenediamine, N, N′-bis (1-methylheptyl) -p-phenylenediamine, N, N ′ -Dicyclohexyl-p-phenylenediamine, N, N'-diphenyl-p-phenylenediamine, N, N'-di (2-naphthyl) -p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine N- (1,3-dimethylbutyl) -N′-phenyl-p-phenylenediamine, N- (1-methylheptyl) N′-phenyl-p-phenylenediamine, N-cycl Hexyl-N'-phenyl-p-phenylenediamine, 4- (p-toluenesulfonamido) diphenylamine, N, N'-dimethyl-N, N'-di-secondary butyl-p-phenylenediamine, diphenylamine, N- Allyldiphenylamine, 4-isopropoxydiphenylamine, N-phenyl-1-naphthylamine, N- (4-tert-octylphenyl) -1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine such as p, p'- Di-tertiary octyldiphenyl-amine, 4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol, 4-octadecanoylaminophenol, di- (4 -Methoxyphenyl) -amine, 2,6-di Tert-butyl-4-dimethylaminomethylphenol, 2,4′-diaminodiphenylmethane, 4,4′-diamino-diphenylmethane, N, N, N ′, N′-tetramethyl-4,4′-diamino-diphenylmethane, 1,2-di [(2-methylphenyl) amino] ethane, 1,2-di- (phenylamino) propane, (o-tolyl) biguanide, di [4- (1 ′, 3′-dimethylbutyl)- Phenyl] amine, tertiary octylated N-phenyl-1-naphthylamine, mono- and dialkylated tertiary butyl / tertiary octyl diphenylamine mixtures, mono- and dialkylated nonyl diphenylamine mixtures, mono- and dialkylated dodecyl diphenylamines Mixtures, mono- and dialkylated isopropyl / isohexyl diphenylamine mixtures, -And dialkylated tert-butyldiphenylamine mixtures, 2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine, mono- and dialkylated tert-butyl / tertiary octylphenothiazine mixtures, mono -And mixtures of dialkylated tertiary octylphenothiazines, N-allylphenothiazine, N, N, N ', N'-tetraphenyl-1,4-diaminobut-2-ene, N, N-bis (2,2,6 , 6-Tetramethylpiperidin-4-yl) hexamethylenediamine, bis (2,2,6,6-tetramethyl-piperidin-4-yl) sebacate, 2,2,6,6-tetramethylpiperidino -4-one, 2,2,6,6-tetramethylpiperidino-4-ol.

Further antioxidants Ascorbic acid (vitamin C), aliphatic or aromatic phosphites, esters of thiodipropionic acid or thiodiacetic acid, or salts of dithiocarbamic acid or dithiophosphoric acid, 2,2,12,12-tetra Methyl-5,9-dihydroxy-3,7,11-trithiatridecane or 2,2,15,15-tetramethyl-5,12-dihydroxy-3,7,10,14-tetrathiahexadecane.

Metal deactivator, for example for copper
1. Benzotriazole and its derivatives : 2-mercaptobenzotriazole, 2,5-dimercaptobenzotriazole, 4- or 5-alkylbenzotriazole (eg toltriazole) and their derivatives, 4,5,6,7-tetrahydrobenzo Triazole, 5,5′-methylene-bisbenzotriazole; Mannich base of benzotriazole or toltriazole, such as 1- [di (2-ethylhexyl) aminomethyl] toltriazole and 1- [di (2-ethylhexyl) aminomethyl Benzotriazole; alkoxyalkylbenzotriazole, such as 1- (nonyloxymethyl) benzotriazole, 1- (1-butoxyethyl) benzotriazole and 1- (1-cyclohexyloxybutyl) toltriazo The
2. 1,2,4-triazole and its derivatives : 3-alkyl- (or aryl-) 1,2,4-triazole, Mannich bases of 1,2,4-triazole, such as 1- [di (2- Ethylhexyl) aminomethyl] -1,2,4-tolutriazole; alkoxyalkyl-1,2,4-triazole, such as 1- (1-butoxyethyl) -1,2,4-triazole; acylated 3-amino -1,2,4-triazole.
3. Imidazole derivatives : 4,4′-methylenebis (2-undecyl-5-methylimidazole); bis [(N-methyl) -imidazol-2-yl] carbinol-octyl ether.
4). Sulfur atom-containing heterocyclic compounds : 2-mercaptobenzothiazole, 2,5-dimercapto-1,3,4-thiadiazole, 2,5-dimercaptobenzothiadiazole and derivatives thereof; 3,5-bis [di (2 -Ethylhexyl) aminomethyl] -1,3,4-thiadiazolin-2-one.
5. Amino compounds : salicylidene-propylenediamine, salicylaminoguanidine and salts thereof.

Rust inhibitor 1. Organic acids, their esters, metal salts, amine salts and anhydrides : alkyl- and alkenyl succinic acids and their partial esters of alcohols, diols or hydroxycarboxylic acids, partial amides of alkyl- and alkenyl succinic acids, 4-nonylphenoxy Acetic acid, alkoxy- and alkoxyethoxycarboxylic acids such as dodecyloxyacetic acid, dodecyloxy (ethoxy) acetic acid and their amine salts, and also N-oleoyl sarcosine, sorbitan monooleate, lead naphthenate, alkenyl anhydride Acids such as dodecenyl succinic anhydride, 2- (2-carboxyethyl) -1-dodecyl-3-methylglycerol and their salts, in particular their sodium and triethanolamine salts.
2. Nitrogen atom-containing compounds :
2.1 Tertiary aliphatic or cycloaliphatic amines and amine salts of organic or inorganic acids such as oil-soluble alkyl ammonium carboxylates and also 1- [N, N-bis (2-hydroxyethyl) amino ] -3- (4-Nonylphenoxy) propan-2-ol.
2.2 Heterocyclic compounds such as: substituted imidazolines or oxazolines such as 2-heptadecenyl-1- (2-hydroxyethyl) -imidazoline.
3. Sulfur atom-containing compound : barium dinonylnaphthalenesulfonate, calcium petroleum sulfonate, alkylthio-substituted aliphatic carboxylic acid, ester of aliphatic 2-sulfocarboxylic acid or a salt thereof.

Extreme pressure and antiwear additives sulfur atom containing compounds and halogen atom containing compounds such as chlorinated paraffins, sulfurized olefins and vegetable oils (soybean / rapeseed oil), alkyl or aryl di- or trisulfides, benzotriazole or derivatives thereof, For example, bis (2-ethylhexyl) aminomethyl toltriazole, dithiocarbamate, such as methylene-bis-dibutyldithiocarbamate, 2-mercaptobenzothiazole derivative, such as 1- [N, N-bis (2-ethylhexyl) amino Methyl] -2-mercapto-1H-1,3-benzothiazole, derivatives of 2,5-dimercapto-1,3,4-thiadiazole, such as 2,5-bis (tertiary nonyldithio) -1,3,4 -Thiadiazole.

Friction coefficient reducing agent Lard oil, oleic acid, tallow, rapeseed oil, sulfurized fat, amine. Further examples are described in EP-A-0 565 487.

Further additives
1. Viscosity index improver : polyacrylate, polymethacrylate, vinyl pyrrolidone / methacrylate copolymer, polyvinyl pyrrolidone, polybutene, olefin copolymer, styrene / acrylate copolymer, polyether.
2. Pour point depressants : poly (meth) acrylate, ethylene / vinyl acetate copolymer, alkyl polystyrene, fumarate copolymer, alkylated naphthalene derivative.
3. Dispersants / surfactants : polybutenyl succinamides or imides, polybutenylphosphonic acid derivatives, basic magnesium, calcium and barium sulfonates and phenolates.

Special Additives For use in water / oil metal working fluids and hydraulic fluids Emulsifiers : petroleum sulfonates, amines such as polyoxyethylated fatty amines, nonionic surfactants;
2. Buffer : alkanolamine;
3. Biocides: triazines, thiazolinones, tris - nitromethane, morpholine, pyridinium Dench ol sodium (sodium pyridenethiol);
4). Processing speed improvers : calcium sulfonate and barium sulfonate.

  The above ingredients are added to the composition using conventional mixing methods in a manner known per se. It is also possible to produce a concentrate or so-called additive package using compound (I) or a mixture thereof and further additives as desired, said concentrate or so-called additive package being a lubricant of interest. Dilute as necessary to a concentration for use. The composition of the components in the concentrate is such that the concentrate is liquid at room temperature without further addition of component b) or solvent.

The present invention also provides a) at least one compound (I) wherein R ₁ , R ₂ , R ₃ , X and Y are as defined, further optional additives, and b) It also relates to a concentrate containing a base oil of lubricating viscosity.

The invention also consists in adding to the lubricant a composition comprising at least one compound (I), wherein R ₁ , R ₂ , R ₃ , X and Y are as defined. It also relates to a method for improving the use performance of the lubricant.

１．１ アクリル酸ｎ−ブチルエステル１４．１ｇ（０．１１０ｍｏｌ）をｎ−オクタデシルアミン２８．４ｇ（０．１００ｍｏｌ）へ６０℃において１０分間かけて滴下添加し、透明な反応混合物を１００℃において２時間攪拌し；冷却した粗生成物をヘキサン１００ｍＬに溶解し、濾過し、水５０ｍＬで２度洗浄した。有機相を回転エバポレーターを使用した蒸発によって濃縮し、残渣を減圧下で乾燥させ、透明な無色の中粘度のオイル４０．０ｇを得た。
１．２ 無水琥珀酸３．１ｇ（０．０３０ｍｏｌ）を結果として生じた中間生成物１１．９ｇ（０．０３０ｍｏｌ）へ添加し、透明な反応溶液を１００℃において１時間攪拌した。冷却した粗生成物をヘキサン１００ｍＬに溶解し、濾過し、水４０ｍＬで２度洗浄した。ヘキサン溶液を回転エバポレーターを使用した蒸発によって濃縮し、残渣を減圧下で乾燥させた。放置すると結晶化する透明な黄色のオイル１３．７ｇ（理論量の９２％）を得た。
Ｍ．ｐ．：５０−５２℃；元素分析：Ｃ ７０．２４％（計算値６９．９８％）、Ｈ １０．９１％（計算値１１．１４％）、Ｎ ２．８０％（計算値２．８１％）。 The following examples illustrate the invention:
Examples m. p. Indicates melting point. Drying under reduced pressure (100 ° C., about 0.05 mbar).
Example of synthesis
Example 1
N- (2-n-butoxycarbonylethyl) -N- (n-octadecyl) -succinic acid monoamide

1.1 14.1 g (0.110 mol) of acrylic acid n-butyl ester is added dropwise to 28.4 g (0.100 mol) of n-octadecylamine over 10 minutes at 60 ° C., and the transparent reaction mixture is added at 100 ° C. Stir for 2 hours; the cooled crude product was dissolved in 100 mL of hexane, filtered and washed twice with 50 mL of water. The organic phase was concentrated by evaporation using a rotary evaporator and the residue was dried under reduced pressure to give 40.0 g of a clear colorless medium viscosity oil.
1.2 3.1 g (0.030 mol) of succinic anhydride was added to 11.9 g (0.030 mol) of the resulting intermediate product and the clear reaction solution was stirred at 100 ° C. for 1 hour. The cooled crude product was dissolved in 100 mL of hexane, filtered and washed twice with 40 mL of water. The hexane solution was concentrated by evaporation using a rotary evaporator and the residue was dried under reduced pressure. 13.7 g (92% of theory) of a clear yellow oil that crystallizes on standing.
M.M. p. : 50-52 ° C; elemental analysis: C 70.24% (calculated value 69.98%), H 10.91% (calculated value 11.14%), N 2.80% (calculated value 2.81%) .

２．１ アクリル酸ｎ−ドデシルエステル２６．７ｇ（０．１０ｍｏｌ）を３−ｎ−ブトキシプロピルアミン１３．３ｇ（０．１００ｍｏｌ）へ２０分間かけて滴下添加し、反応混合物を１００℃において２時間攪拌し；冷却した粗生成物を減圧下で乾燥させ、透明な無色の低粘度のオイル３７．０ｇを得た。
２．２ 無水琥珀酸４．２ｇ（０．０４０ｍｏｌ）を結果として生じた中間生成物１４．９ｇ（０．０４０ｍｏｌ）へ添加し、反応溶液を２時間攪拌し；冷却した粗生成物をヘキサン１００ｍＬに溶解し、濾過し、水３０ｍＬで３度洗浄した。ヘキサン溶液を回転エバポレーターを使用した蒸発によって濃縮し、残った生成物を減圧下で乾燥させ、中粘度の透明な黄色オイル１８．０ｇ（理論量の９５％）を得た。
ｎ_D ²⁰ １．４６７０；元素分析：Ｃ ６６．８５％（計算値６６．２１％）、Ｈ １０
．５４％（計算値１０．４７％）、Ｎ ２．７２％（計算値２．９７％）。 Example 2
N- (3-n-butoxypropyl) -N- (2-n-dodecyloxycarbonylethyl) -succinic acid monoamide

2.1 26.7 g (0.10 mol) of acrylic acid n-dodecyl ester are added dropwise to 13.3 g (0.100 mol) of 3-n-butoxypropylamine over 20 minutes, and the reaction mixture is heated at 100 ° C. for 2 hours. Stirring; the cooled crude product was dried under reduced pressure to yield 37.0 g of a clear, colorless, low viscosity oil.
2.2 4.2 g (0.040 mol) of succinic anhydride are added to 14.9 g (0.040 mol) of the resulting intermediate product and the reaction solution is stirred for 2 hours; the cooled crude product is added to 100 mL of hexane. , Filtered and washed 3 times with 30 mL of water. The hexane solution was concentrated by evaporation using a rotary evaporator and the remaining product was dried under reduced pressure to yield 18.0 g (95% of theory) of a medium viscosity clear yellow oil.
n _D ²⁰ 1.4670; Elemental analysis: C 66.85% (calculated value 66.21%), H 10
. 54% (calculated value 10.47%), N 2.72% (calculated value 2.97%).

３．１ ４−アクリロイルモルホリン５．８ｇ（０．０４０ｍｏｌ）をオレイルアミン（アルミーンＯ（登録商標：Ａｒｍｅｅｎ））１０．７ｇ（０．０４０ｍｏｌ）へ６０℃において１０分間かけて滴下添加し、反応混合物を１００℃において１時間攪拌し、冷却した粗生成物を減圧下で乾燥させ、透明な淡黄色で低粘度のオイル１６．０ｇを得た。
３．２ 無水琥珀酸４．１ｇ（０．０４０ｍｏｌ）を結果として生じた中間生成物１６ｇ（０．０４０ｍｏｌ）へ添加し、反応溶液を１００℃において１時間攪拌し、冷却した粗生成物をヘキサン２００ｍＬ及びブライン（飽和ＮａＣｌ）１００ｍＬと振盪した。３相のまん中の相をそれぞれブライン３０ｍＬを使用して更に３度洗浄し、トルエン１００ｍＬ中に溶解し、濾過し、回転エバポレーターを使用した蒸発によって濃縮し；残った生成物を減圧下で乾燥させた。冷却すると濁る透明な黄色オイル１５．６ｇ（理論量の７７％）を得た。
元素分析：Ｃ ６８．２４％（計算値６８．４７％）、Ｈ １０．２３％（計算値１０．３０％）、Ｎ ５．３４％（計算値５．５１％）。 Example 3
N- (2-morpholinocarbonylethyl) -N- (n-octadecyl) -succinic acid monoamide

3.1 5.8 g (0.040 mol) of 4-acryloylmorpholine was added dropwise to 10.7 g (0.040 mol) of oleylamine (Alumine O® Armen) over 10 minutes at 60 ° C. and the reaction mixture was The mixture was stirred at 100 ° C. for 1 hour, and the cooled crude product was dried under reduced pressure to obtain 16.0 g of a clear, pale yellow, low-viscosity oil.
3.2 4.1 g (0.040 mol) of succinic anhydride are added to 16 g (0.040 mol) of the resulting intermediate product, the reaction solution is stirred at 100 ° C. for 1 hour and the cooled crude product is added to hexane. Shake with 200 mL and brine (saturated NaCl) 100 mL. The phases in the three phases are washed three more times using 30 mL of brine each, dissolved in 100 mL of toluene, filtered and concentrated by evaporation using a rotary evaporator; the remaining product is dried under reduced pressure. It was. On cooling, 15.6 g (77% of theory) of a clear yellow oil which became cloudy was obtained.
Elemental analysis: C 68.24% (calculated value 68.47%), H 10.23% (calculated value 10.30%), N 5.34% (calculated value 5.51%).

表１

Example 4
The following compound (I) could be prepared analogously to Examples 1 to 3:

Table 1

Application examples
Example 5
Corrosion protection test (for industrial oil, circulating oil, turbine oil and hydraulic oil containing active ingredients) according to ASTM D 665 (= DIN 51585)

300 mL of the blended oil was mixed with 30 mL of synthetic seawater by stirring at 60 ° C. for 24 hours, and at the same time, a steel round rod was immersed.
After 24 hours of contact, the steel rod was subjected to a visual corrosion test. Each test was performed twice. The base formulation is based on standard SN VG46 mineral oil stabilized using antioxidants and metal deactivators. In the test, the active ingredient was used at a concentration of 0.1 mmol / kg (corresponding to 0.03 to 0.06 wt% or 300 to 600 ppm). See Table 2 for results.
・ 0: No corrosion ・ 1: Slightly corroded (corrosion part with a diameter of less than 1 mm is <6)
・ 2: Some degree of corrosion (corrosive surface <5%)
・ 3: considerable corrosion (corrosion surface> 5%)

Example 6
Test of filter capacity in the presence of calcium ions 0.3 g of distilled water and 30 ppm of calcium in the form of a calcium detergent (6.9% Ca) were added to 300 g of the test formulation. The mixture was homogenized for 5 minutes at maximum rotation speed in a four-blade mixer. The emulsion was stored at 70 ° C. (+/− 2 ° C.) for 96 hours and then stored in the dark at room temperature for an additional 48 hours. The test was stopped when precipitation was observed. Prior to filtration, the test mixture was homogenized again by shaking vigorously for 1 minute. The mixture was then filtered by passing through a 0.8 μmillipore® filter (AAWP04700) using compressed air with a positive pressure of 1 bar (+/− 0.05 bar). The time required to filter 50, 100, 200 and 300 mL of the test mixture was measured. The filtration index FI was calculated as the average value from two measurements according to the following formula (see AFNOR NFE48-691):

_{FI = (t 300mL -t 200mL)} / 2 (t 100mL -t 50mL)
FI = 1 means that no resistor has accumulated in the filter.
FI <2 is a necessary condition for passing the test.
If the filter was blocked, the volume of oil passed by after 60 minutes was recorded. Table 2

Claims (8)

a) at least one formula

[Where:
R ₁ represents an alkyl group having 1 to 22 carbon atoms, an alkyl group having 2 to 22 carbon atoms substituted with a hydroxy group, —C (═O) —, —O—C (═O) —, or — C 2 -C 22 alkyl group interrupted by NR _a —C (═O) —, —O—, —S—, —NR _a —, —C (═O) —O— or —C ( ═O) an alkyl group having 3 to 22 carbon atoms interrupted by —NR _a — (wherein R _a represents a hydrogen atom or an alkyl group having 1 to 22 carbon atoms), phenyl group, benzyl group Represents a substituent selected from the group consisting of 1- or 2-phenylethyl group, 2-phenoxyethyl group, furfuryl group, 1-naphthyl group, 1-naphthylmethyl group, cyclohexyl group, cyclohexylmethyl group and isobornyl group. ;
R ₂ and R ₃ represent a hydrogen atom, or one of R ₂ and R ₃ represents a hydrogen atom and the other represents a methyl group;
X represents a carboxy group or a carboxylate and Y ⁺ represents a salt-forming cation suitable for a lubricant composition; or X is a cyano group, an ester with an alkyl group having 1 to 22 carbon atoms Carboxy group, hydroxy-carboxy group esterified with an alkyl group having 2 to 22 carbon atoms, -C (= O)-, -C (= O) -O-, or -C (= O) -NR _a - interrupted by the esterified carboxy group with an alkyl group having a carbon number of 2 to 22, -O -, - S - , - NR a -, - O-C (= O) - or by - Carboxyl group esterified with an alkyl group having 3 to 22 carbon atoms interrupted by NR _a — (C═O) — (wherein R _a represents a hydrogen atom or an alkyl group having 1 to 22 carbon atoms). Express) Nyl group, benzyl group, 1- or 2-phenylethyl group, 2-phenoxyethyl group, furfuryl group, 1-naphthyl group, 1-naphthylmethyl group, cyclohexyl group, cyclohexylmethyl group A carboxy group esterified with an isobornyl group and a partial formula

(Wherein R _b and R _c each independently represent a hydrogen atom, an alkyl group having 1 to 22 carbon atoms, or a 2-hydroxyethyl group, or R _b and R _c are taken together) An alkylene group having 2 to 8 carbon atoms, an alkenylene group having 2 to 8 carbon atoms, an alkadienylene group having 2 to 8 carbon atoms, or 2 to 8 carbon atoms interrupted by —O— or by —NR _a —. Represents an alkylene group having 8 carbon atoms, an alkenylene group having 2 to 8 carbon atoms, or an alkadienylene group having 2 to 8 carbon atoms, and R _a is as defined above. Represents a derivatized carboxy group; and
Y ⁺ represents a hydrogen ion or a salt forming cation suitable for a lubricant composition. And a compound represented by:
b) A composition comprising a base oil of lubricating viscosity. a) at least one compound (I)
[Where:
R ₁ represents an alkyl group having 1 to 22 carbon atoms, an alkyl group having 2 to 22 carbon atoms substituted with a hydroxy group, —C (═O) —, —O—C (═O) —, or — C 2 -C 22 alkyl group interrupted by NR _a —C (═O) —, —O—, —S—, —NR _a —, —C (═O) —O— or —C ( ═O) an alkyl group having 3 to 22 carbon atoms interrupted by —NR _a — (wherein R _a represents a hydrogen atom or an alkyl group having 1 to 22 carbon atoms), phenyl group, benzyl group Represents a substituent selected from the group consisting of 1- or 2-phenylethyl group, 2-phenoxyethyl group, furfuryl group, 1-naphthyl group, 1-naphthylmethyl group, cyclohexyl group, cyclohexylmethyl group and isobornyl group. ;
R ₂ and R ₃ represent a hydrogen atom, or one of R ₂ and R ₃ represents a hydrogen atom and the other represents a methyl group;
X represents a cyano group, a carboxy group esterified with an alkyl group having 1 to 22 carbon atoms, a carboxy group esterified with a hydroxy-alkyl group having 2 to 22 carbon atoms, -C (= O)-, A carboxyl group esterified with an alkyl group of 2 to 22 carbon atoms interrupted by —C (═O) —O— or —C (═O) —NR _a —, —O—, —S—, _{-NR a -, - O-C} (= O) - or by _{-NR a - (C = O)} - a carboxyl group esterified with an alkyl group having 3 to carbon atoms which is interrupted 22 by (wherein, R _a represents a hydrogen atom or an alkyl group having 1 to 22 carbon atoms), a phenyl group, a benzyl group, a 1- or 2-phenylethyl group, a 2-phenoxyethyl group, a furfuryl group, 1-naphthyl group , 1 in naphthylmethyl group, cyclohexyl group, cyclohexyl methyl group, a carboxyl group esterified and subexpressions isobornyl group (A) (wherein, R _b and R _c are independently of each other, hydrogen atom Represents an alkyl group having 1 to 22 carbon atoms or a 2-hydroxyethyl group, or R _b and R _c together represent an alkylene group having 2 to 8 carbon atoms, a group having 2 to 8 carbon atoms, An alkenylene group, an alkadienylene group having 2 to 8 carbon atoms, or an alkylene group having 2 to 8 carbon atoms interrupted by —O— or by —NR _a —, an alkenylene group having 2 to 8 carbon atoms or the number of carbon atoms 2 to represent alkadienylene group 8, R _a is selected from the group consisting of carbamoyl group represented by are as defined above.) induction It represents a reduction carboxy group; and,
Y ⁺ represents a hydrogen ion or a salt forming cation suitable for a lubricant composition. ];as well as,
2. The composition of claim 1 comprising a base oil of lubricating viscosity. a) at least one compound (I)
(Where
R ₁ is an alkyl group having 1 to 22 carbon atoms, —C (═O) — or an alkyl group having 2 to 22 carbon atoms interrupted by —O—C (═O) —, —O— Represents a substituent selected from the group consisting of an alkyl group having 3 to 22 carbon atoms, a phenyl group and a benzyl group interrupted by -S- or by -C (= O) -O-;
R ₂ and R ₃ represent a hydrogen atom;
X is a cyano group, a carboxy group esterified with an alkyl group having 1 to 22 carbon atoms, a carboxy group esterified with a hydroxy-alkyl group having 2 to 22 carbon atoms, or -C (= O)-. Or a carboxy group esterified with an alkyl group of 2 to 22 carbon atoms interrupted by -C (= O) -O-, -O-, -S- or -O
A group consisting of a carboxy group esterified with an alkyl group having 3 to 22 carbon atoms interrupted by-(C = O)-, a carbamoyl group represented by the partial formula (A) defined as a heterocyclic carbonyl group Represents a derivatized carboxy group selected from: and
Y ⁺ represents a hydrogen ion, ammonium, (alkyl having 1 to 4 carbon atoms) _{1 to 4} ammonium or (2-hydroxyethyl) _{1 to 4} ammonium. );as well as,
2. The composition of claim 1 comprising a base oil of lubricating viscosity. a) at least one compound (I)
(Where
R ₁ represents a substituent selected from the group consisting of an alkyl group having 1 to 22 carbon atoms, an alkyl group having 3 to 22 carbon atoms interrupted by —O—, a phenyl group, and a benzyl group;
R ₂ and R ₃ represent a hydrogen atom;
X is a cyano group, a carboxy group esterified with an alkyl group having 1 to 22 carbon atoms, a carboxy group esterified with an alkyl group having 3 to 22 carbon atoms interrupted by —O—, and piperidyl Represents a derivatized carboxy group selected from the group consisting of a carbamoyl group represented by the partial formula (A) defined as a nocarbonyl group, a piperazinylcarbonyl group or a morpholinocarbonyl group; and
Y ⁺ represents a hydrogen ion, ammonium, (alkyl having 1 to 4 carbon atoms) _{1 to 4} ammonium or (2-hydroxyethyl) _{1 to 4} ammonium. );as well as,
2. The composition of claim 1 comprising a base oil of lubricating viscosity. a) at least one compound (I)
(Where
R ₁ represents a substituent selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an alkyl group having 3 to 18 carbon atoms interrupted by —O—, a phenyl group, and a benzyl group;
R ₂ and R ₃ represent a hydrogen atom;
X represents a carboxy group and Y represents ammonium, (alkyl of ₁ to 4 carbon atoms) _{1 to 4} ammonium or (2-hydroxyethyl) _{1 to 4} ammonium; or
X represents a carboxylate group, or esterified with a cyano group, a carboxy group esterified with an alkyl group having 1 to 18 carbon atoms, or an alkyl group with 3 to 18 carbon atoms interrupted by —O— Represents a derivatized carboxy group selected from the group consisting of a selected carboxy group and a morpholinocarbamoyl group; and
Y represents a hydrogen atom, ammonium, (alkyl having 1 to 4 carbon atoms) _{1 to 4} ammonium or (2-hydroxyethyl) _{1 to 4} ammonium. );as well as,
2. The composition of claim 1 comprising a base oil of lubricating viscosity. The composition according to claim 1, comprising a base oil having a lubricating viscosity used for b) hydraulic fluid or metal working fluid, grease, gear oil or engine oil. A concentrate comprising at least one compound (I), wherein R ₁ , R ₂ , R ₃ , X and Y are as defined in claim 1. A method for improving the serviceability of a lubricant, comprising adding at least one composition according to claim 1 to the lubricant.